Document 8EXZJJdYVe4NxYY6oKp2Jjq5

cer 3nIn.i~r7rnn.allCCoL~rimrnssgppoo-nndde2enn1cc-ee24-07 (eso only) W3DRBB..LI, WALA~~.!... B~RBp~aaeaelncafcignarnonienete-ro--n-2-/~22n2-12~2.-11-w22--2o~0R2~0e--4070-00~5R55i~cM~(kHMe(emeexmrmo/oaooc-ooenna3nlyis3lyyh)-)r)6e3n-t0)4 (W/Actachnenc) . $F1ID. H. H. F. D. Pearlson/D. R. ~icker - 223-6S-04 (W/~t~achment) Gerainfyeit"h2207212365-330303(Me(mno/aotntlayc)hment) Gri~fith - 220-2E-02 (H/Attachment) S. M. Leahy - 220-13E-33 ~Memo b: 3. J. . D. LAZENTE LAZERTE - - CCOOMMMMEERRCCIIAALL CCHHEEMVIICCAALLSS DDIIVVIISSIIOONN - = 223366--I1B8--2211 FF~O.~RR.. LL.. BBOOHMOONN -~ EENNVVIIRROONNMNEENNTTAALL LLAA~B//EEEE && FPCC -= 2211--226W--0055 SS~0: FFAATTEE OOFF FFLLUUOONROOCCHHEEMVIICCAALLSS PPHHAASSEE TIXI 3m on way ~le. MAY 25, ~S, I1~98833 ~ AAfEEtuultttrruaattocchhrhheeoeerrcdshaeenvvftiaaoocirlraoulaayystcoo.eeuurrssereFrleolerevevcicibteetaewwecddkiissesernnavavauiinrrppgoorrnnoompmPpoaeeorsnnspattaelalaslleffsrprp:oorrmmooppteoehoreurutrrtpiireellossaapbbooooosfrfraaaltt3IooMnrryy ttoo ncCfeoolnniuttoTaaroioinncnmshgeenmoatinnaclaeellxxsytt.eenrnsasiliFvevoeseranbcctaoocmskppigeenrnnodsouiirnuosdmmatopoiuffornpsaoolisn!leseeS,xHxiissftltthuiiesnncggpo.,rcohpeonsiaclals. environmentally relevant information on 3M fluor0chemicals. FnhTerhndeedooerrssaascceeeiiiddeeennetbtbnyiyi,ffiooiucuDcrraaEFHssannppgvveeeiccinrttz,ssoenrWommo.efefnntcPttaaahhllciisksiSSnpcpcgirir.eoeonnppccooG.eessaalAlANddavvnhhtiiaa.ssvvoceercassnbbdeeeeC(nn5M... rrCBCeeaaavvssiineeeed,:wvsee)dd: aanndd W. Pearlson, D. Hagen, W. Perkins, G. Hunt, and S. Ban~al). TiTIEhhnTneefufoSoPrrrPhmomhaaaeasstnteeieionontnIcauFwFlhhaasiittcceevhheoorfflieee~dFFellxuttueoooorrreototnchcheehehleemyncciiooccpnnaaeccllcllsuuissSSsiittcoouuonnddnyyttt,hh({aa11ttt99h77ae7a7-l-yl77it39nhc))ooauusggyyehniideellddneeodd RIhafSopSlpRwpupLIeaoeeNvrrrVeeoeerncCnr,thhteamgafaniadeedcrvwwvateelarriIsssnneeffswoohereerermnmneaavvntciieiirereodoooxnnnntmmrteeehohnnamaststeeaalsllybbseeseepeoennfefsfresesSbccirrttsoocsstuuh..egsenhhtttv,SSaiilttnnooitccdhesoeieuutyrrytthchaoaaaatftuttstteeetttdnniihttmmieeiisn,:ooonn wLbnldchlustugigaests the need to reassess the validity of this conclusion. nePPFnveuevrrritisszhriioeossnrtntmeemennetnccnaieetvaailleccwoonnaattaggiineenndnnuucceeiitsseeessstttiooiinnngbb.eetthheeasbotkKssheeeeyyllGeeoccccntooteinnioscconeetnrrinnocoffaalannlccddyhheeUmmttniirrdcciieaaggrllggseserrTSffCbbooAyryr and CsCf{ioouTnnmmrttimmteemuuhrrlnnennaiiraatttttlyyiir..doeonvniwaaehTlTlhewhlleneyyanrrieidennefggiJuJutaalaletppaasiaatttnnnioocnrrgsyya9,n7dr0Sreoebvvoctitdihhheeeeewwscd~thpopeordmrnnoeeo-cctcsnneietaasosittsnsicioaonlnii{lssx yEEfcuufurruuorroonpttdppiehheeereeaadrrnnTvSiCtAh antdne ppPPTsrrrrtRooooiIppppmTeeeeuTrrrrlAttttaiyiyitoeeensdsttoooSowfffbhb~eieononnxaseetccwwreccenuuccsmsnnhiuisaeslivvmtsaeiiattccneeaabc:.iliessoatssaoIIsrnrnaeedyeffaagtthccthretteea,,sdtakkieteiinynyingo.JJnccaarrppiiiaattsnnee,,rrciioasuttphhleeffessooedrer wttiwwtooh the initiation of extensive b~oassay testing. b~RTiieennnccdadeeitinncetntaagtdemmapermmtTomnhapaaaestllriitaa~iinnnesa.sLsdttduu(eisdatiiieefaossonrmccnoot~nnofddduduecebctnmtieeoooddnnasacttcbbrhuyyamatutREiliiinanxkgtgeeirrossnttLL)rraa.oabbnnoogerrcaaettrppootrrrroaoiittieeeenssiinnfluoro EScsbihthinEueenpdanmdGciiiitenccssgaiolisGnEwpeerrrhEoteeuopesnneadsrccnotosnintt,dodeouusccvbttteeh~eeead~yeexxfdccioiorrnnreemttFooeeraroddddifesereree5xxiqtcttouorroaeeecsnmeecteessuillttmyoyiiunmmlsaaasstttlleeioorwovelnistty)yahh..,reesippcnWWooeghhttriieetllnnatetteihieinaattllehhffeelfsrueeeocrtoopPoBinrnrrmooopodrdaotcouuttrchchetteediiroroonnnooprrhhggooauasarfmennaniippsssrrI,mroo1sscc,.eetssshissesesiiydssnnryp~gedecociiifnfsaavraicloaclililiylvlsy:iieettsttiiqhheeuaoossness..eseteivnnoAAeaennnaslsrtuaiitcrfmfipeplioogouonrarorsrtroadaoocninfchtnthagefmmppiiieaetccrclhetatdelloeoffffettchhtee pcCroRonpEdoiEsteiodonnesPheanseneaerIItthneestu3dMynDeeidC~auvttouulrrv,:esAALLanpplleaavnnatel..uation of field Exhi--bit 2573 ua10085483 3MA10065463 3aMM__MWNNGO0000000001188 22557733..00000011 I ETHH PH3.oiygDe.225.Laz1e9r83te Cri OEBufuollerulutooiddcrnaaoogtcccaahheaebnsmbasiaisescceesaasllmssooennnhhtaattsnshheeoccnooeennnnnttvveiiiiwnnrruuoooeennfddmmeenmnttttoooaadllieefxxippppeaarrdnnooddpppeerrsrsotitinidinceeucesscetsoo11ff997c799o3nMtttahhirrnooiuungghgh eeSrfEnnollavvuuugiitosirtrrenoooosernccamhhaeeaatnnmnsheiitsiccsaseaadlsildsssemKk..feinoinouwctliisNNeceeeddnovvgsnceeeeyrr..ttnhheLeewnllT"Teehoahssirnissss.,mOorpPdgdhghiaeaaafpssrpiesesleydsIS1I1atinipldlrssllottduucuddoeecyysxxttiiss-spptterrofocpfpoiioecnnnscstestaoossiuiuvrnreittnoo~bgaassiicc aseCfE~eaealdlscserehhtceiicltosotoinsninvvaeevvtniihiaaddipeesevvaaeedddllgde(oiiofSttppiiismRcooeeiRnnnnesattn)lcyaannllddaainbbuuoossrraeenaattooooorrfrfyydeVvaraAannllLddyii~d{aflnissdeettllrr~auucccottsssuutttruru-ededeiifeesfasseecctttpiiplivvluviiusettsyytthhee relationships (SAR}. pDiD7es"uueeripporrttdooooppooattssthhee~edadmmtaattoghghtnaanatitilttuuttddehheeeestoiossfmfttauutddtteyyhhseebbeecssottrcucueododynnyoddfuuaaccnndtdtueendoddoeuucrroovvele$l5riri0nm0liaa,tt0eett0ddhh0re.mmeeaaeann--Hppyyooeeewwaseersarrr,,e iitt Ppprreereippoaadrreesdat ttaoo ctcoootmmamelenncceeestww~ooarrtkke~iinncottshhtee o33fcrdduqqnudueaarrrttee$rr50011,690880330... we are SwSIIfooeullCCiddoommnmmaaeepperrppccrriieeoaaccnlliiaaattCCeeehhceemymyiioooccuxuaarrllcsssaguusiDiDpdidiovavanininsscscoieieroonnaannddccaamhnhseenollotppt ffiuunnnddidetthnhiitssifysstituunddgyy,a, n II in i~entifying an SVSaIhlhTotoEueulrlddnCaotnyyoetouaucstphhoaaynvvoeseuo~aasnnyhyoroqrqutcueloesysstptiotioononsnsoss,re,.t ppluleepassaseeTeccvaaillellwmpemeeeaatttin77g7788-o-55n1100t4h4.i.s I proposal. will contact proposal. you shortly to se~ up a review meeting on this up/cer AARttLttBaa/ccchehlmmeenntt:: PPrrooppoossaall,, ""FFaattee ooff FFlluuoorroocchheenniiccaallss =- PPhhaassee I1I1" 22557733..00000022 uato0ssdse 3MA10065464 au_Nooococto 3M_MNO0000019 3M "CONFIDENTIAL" FATE OF rLuOROCHENICALS - PmaSE IT Prepared by: Environmental Environmental LLaabboorraattoorryy ((E2E2 && 5PC)) Eo AA.. RReeiinneedr,, Ecdaisttoorr aHayy 2200,, 11998833 22557733..00000033 3aMaAt1o0e0s65i4s6s5 SM_NO00C20 3M_MNDOOOOr]20 = -tIe- fr-- ACKNOWLEDGMENTS 32MM ECA OMADENTIAL S2Tth0hhrl1riossogugpnrphrraoooneuppe~ooessnaaa3Slll~N,,trrhFpeebaEpporrrtrteeiaissccceeaonunlrttlayssacrlSlttytyhhaeerpptecac.ssoottmmbbilaannnneedd8dpprereefefsfsfeoeonrnrttttssmeooenffmtbeemmrraassnnyyooFfppeerttcshhaoeennss EESPSDfiRprpnSeoevrrvcdcliiiuirracacaoeeltlntmssmi;,ettonhhntnRaaainndlkkkrsseorLSnwaaarrbLeeoaCRabreooaexeerxtixiatotciteereonnayirddooieesSieddtycsa,ftdrtifoooo.rCnCCeecsoneomtamtrmoethaerilricncsfigiReaaelllwseiettaCCahrhhdceehmoslsiHccC iaapslletssro,,ttE ihAAneogenrcniiitcccauutllstt.uurraall T Ie TFonAB LRe ETneoTtnnIt Lon E5X% SHheTormaeet,na. Services, an~ 3M Toxicology for sharing with us pertinent information from their experience on selected fluorochemlcals. We apologlze for any misquoted information or incorrect interpretations which may have crept into the flnal p:oposal. :. 22557733..00000044 auntonesess 3MA10065466 au vooones 3M_MNODO00021 lide irDa tio 3L M COr NADENTIAL out or corres TABLE OF CONTENTS Jr pe3 ABSTRACT J-------- s ORGANIZATION OF REPORT . svesooucrion s I. INTRODUCTION 5. Backarouns : A. Background 3 bE canna concen } B, Remainlng:Environmental Concerns 4 & nmi : CD5.. CTCoiosmstitnssg' 6 6 6 st. remmotmontore wow sesgeseER , FLUORO~HEMICAL RISK ASSESSMENT FA -- 1 II. COMMON CONCERNS WITH 3M FLUOROCHEMICALS i0 2. siructyre hevivity Reissionshipe 10 A. Snructure Activity RelatlonshIps i0 bop u B. Field Studies 20 hn # C. Incineration 27 Iv. VIROWENTAL PROPERTIES OF PLOGROCWENICN. CLASSES 79 IV. ENVIRONMENTAL PROPERTIES OF LUOROCHEMICAL CLASSES 29 1 TTL 2 A. Inert Liquids 29 bE aie sui 3 ~. Low MW Acids and Their Salts 34 Efe mac 3 C. Surfactants 36 5 peta i D. Phosphates 55 Egon i E. Alcohols 58 Edi. 8 F. Acrylates 69 otha % G. Urethanes 77 ---- u ~. FLUOREL~ an~ KEL-F~ Polymers 81 I Ema i I. Catalysts 82 v.. so o SUMMARY 83 REFERENCES 93 APPENDLR 3 ~ MGONFIC TOKICETY RANKING SYSTEN J APPENDIX I - AQUATIC TOXICITY RANKING SYSTEM A-I JR p------ APPENDIX II - KEY TO CHEMICAL PRODUCTS DISCUSSED IN REPORT A-2 aeverEn 113 = wakes on G-RSIOLARESED FULGROCHNIGHS 3-6 APPENDIX III - NEEDS FOR 14C-RADIOLABELED LUOROCHEMICALS A-6 Jy as APPENDIX IV - IMPORTANCE OF SAR TO U.S. EPA A-8 aurtoossir 3MA10065467 awsnooneczz 3M_MN00000022 2573.0005 --e-- e ------r-- r ---------------- "thie oiiio T TABLAESB AANNDDLFFIE IGGUURRS ES TIT IDINTIAL TABLE TABLE 3 1 - - DDPAATToAA tOONN FFLLUOeOORRnOOeCCHHSEErPMiIICCmAAnLLSSpaIInNNeCC}LLUUDDEEDD In IN FATE FATE OF OF 5 FIGURE FIGURE 1111-+ FBILIEMUNEPOPOROoRORCTE~AAENNmTMTICPPAAaALTTSHNIASKYTSSUDYOOFFPAAANNRTOORRI GGAAWNIICC CHENICNL CHEMICAL Ix IN 12 12 TASLE TABLE 3 2 - - Ae ACCTHUUEEEOO~UESER NVSISOROLLOUUNBBMISELLNIITTTEIIEESShAAUNDDSOOCCrTEAAeNNOOeLL/WAATTEERR PARTITION PARTITION TABLE 3 ~ CFOLECOFNFIICCEIEMNTESSUORFENOERNGTASNIACTCTOHMEPOUDENCDASTUR FIAVT a16 TABLE TABLE TABLE ~ 4 -- - SfSFUULiMMUrMPOAAReRRIsYDYEOOFFMEAEESNNUVVRIIERRMOOENMNMETENSNTTAAATLL EFTECTS OF FLUGRINERT THE DECATUR PLANT EFFECTS OF FLUORINERT 3221 32 TABLES TABLE S - - TTLOOIXXQIIUCCCIIIDRTTSYYEOOFBFANLNaEaOSOHH oFNNEEUUSTTRRESASALLIRZAIEEGDD TFFLLUUOORROGCCHHEIMNIICCAALL ACIDS ACIDS 35 35 mats TABLE 6 - - FASsEONoLuDE UwBOBIITLLHIIETERYYSAAAS NNLDDTcSOcCOTTFaANToOHLE LE/SWEAATTAEECSRIDSPsAARRTTIITzIIOONN 37 abt TABLE 7 7 - - f ErODPami ADATIONt DATA s OF NOMSCLUENT-CONTATNDYG COEFFICIENTS OF FLUOROCHENICAL SURFACTANT PRODUCTS BIOD~GRADATION DATA ON NONSOLVENT-CONTAINING 41 41 TABLE - AFGLOUNOTRIOCC~EBMIIOCAASLEAYSURDAFTAACTOANTSth S628 AWD EAZ B01 44 ATARBLLEE 8 - - AIQSURATIJCenBnI.OALSosSgAY DDAATTAA OFNORLRFL5I6C2R5CCHAENDNICEAAIL 80021 44 TABLE TABLE TABLF 10 + opwenrBvTa ROWBYRTALepsrrEsCES SATA On 9 - SSUIu~SRPFmACC9T6TA-ANHVRTS.S LC500 DATA FCR FLUOROCREMICAL I0 - OTRER E~IRONMENTAL EFFECTS DATA ON 45 47 TABLE 11 - BFELoUAOSRSOACYHEDMAITCAALOFSURTAFA3C8T4A4N-T4S AD Ln 4197-2 o TTAABBLLEE 1II3 -- T~OIMOAISCSIATYY ODFATAACROYNLALTRE38P4R4O-D4UCEASND70LRAQ4U1A9T7-I2C =63 TABLE 12 - TOXICITY OF ACRYLATE PRODUCTS TO AQUATIC 72 THRLE TABLE 13 13 = - AAOHcCReuUGAAAiTTNsIIICSCsMSTTOOXXIICCIITTYY DATA DATA OF ON URETHANE ~RET~ANE CoTRIING CONTAINING 79 79 as TABLE 14 14 = - SsPHUo~MrOMeDAaS RrCYyTSoOFrERsEiCcOoMmMmEuNnDeEeD stustes STUDIES on ON w84 wats 15 - sFLuUOpROaC~EoMFICsArLososto work w TABLE 15 - SCHEDULE OF PROPOSED ~[ORK 88 awar0%5468 3MA10065468 auvoxmec2s 3M_MN00000C23 22557733..00000066 NT a IM LL TIENTIAL are or rrscsoouenicass - ewse 11 FATE OF FLUOROCHEMICALS - PHASE rssrac ABSTRACT his report suvious che Environmental Lavorscory's krovlegge This report reviews the Environmental Laboratory's knowledge aE Rt eg py through the end of 1982 of the environmental behavior of 3M SSISChnoSh CE Ture Seay neces co fluorochemicals and proposes areas of further study necessary to resolve important unanswered questions. ------ ORGANIZATION OF RE~ORT he arrangenent of the repose fs as foliovss The arrangement of the report is as follows: t. moowczion, Tata section sores fou greast INTRODUCTION. This section covers four areas: A) Background, B) Remaining Environmental Concerns, oF HRN RR C) Time, and D) Cost requirements of the proposal. fr. romomocEmicar nis pssesswerT. The resdes is intzoduces FLUOROCHEMICAL RISK aSSESSMENT. The reader is introduce~ Stet Ina hosine procesass bred by the to the basic approach and thought processes used by the FErErEanEteSeoEiReSnteLatt ana A She heed for SS een ret ap: Environmental Laboratory in assessing the environmental HHI. AScomES SR EotmoceostncrR eete acutesCihvWniLcWe s E FRLeOHlGaKs cGiCoEHnEsNnS IiCpaALJST,hhTisTEphaicstsseacgtzieosnseiss ZII. risks of fluorochemicals and the need for such study. COMMON CONCERNS WITH 3M FLUOROCHEMZCALS. This section is divided into 3 parts: A. Structure-Activity Relationship. This part addresses the need to develop capabilities which will enable prediction of the environmental behaviOr Of EERE MHI fluorochemlcals from structure and physical properties measurements rather than expensive laboratory and f~eld testing. Field Studies. This part discusses a proposal to Rly, DST La perforln on-site studies to evaluate actual ETomnence] Sobepmtrac in and face of sstectes environmental concentration and fate of selected pe a fluorochemicals. The section emphasizes the need to Compa Eieie Sey eats Sieh Ioorstory Sete compare field study data with laboratory data ied predictions. C. jostnerssion. mis pace sesceibes the seed to Incineration. This part describes the need to i rs determine experimentally whether fluorochemicals roan Len Em oh Bu Te hee produce toxic combustion by-products at levels that EE hate son ELomnt eT on the SetEeonainy could have significant effects on the surrounding eitormene! environment. Iv. Evimomen proreaTies oF FLioKchENICAL CLeses. This IV. ENVIRONMENTAL PROPERTIES OF FLUOROCHEMICAL CLASSES. This extensive section reviews existing environmental data and SEE hee eo neh SEL ES assessment needs for each of the following fluorochemicaZ So La i groups: A. Inert Liquids; B. LOw Molecular Weight EE BEI Acids and Their Salts; C. Surfactants; D. Phosphates; E. Alcohols; F. Acrylates; G. Urethanes; H. the re tay = FLUORELe and KeI-F polymers; and I. Catalysts. auntoosees 3MA10065469 sunasoonze 3M_MNO0000024 2573.0007 J iN TAENLTIAL -2JHE AIT SITET gre fh Sheet 9 wee Each of the above fluorochemical groups (A through ~) are Hot Tne IE, further divided into two parts entitled: Background: An examination of current understanding of physical properties, degradabilit~, and TR i Bale bio-effects for each fiuorocbemical group. 2. Besgmmented sestiony responia for fares suusies Recommended Testing: Proposals for further studies heeded in ~rder to fill important gaps in present knowledge. Decision points, expected test output, Eh aE : and priorities are include~. SUV~ARY. Th~s section reviews in tabular fo~m the proposed work and cost for this Pa~t II of the Fate of or. E EELLA AL SEIalee] Th issnsd saps Fluoroche~icals Study. VI. REFERENCES. A list Of cited 3M internal reports and published literature ~our appendixes follow the report: Appendix I: The NIOSH Aquatic Toxicity Ranking System. Appendix II: "Key to Chemical Products Discussed in the Report." This appendix provides the class, chemical code name, and structure or formulation of chemical products mentioned in the report text. 6ppen~x III: "Needs For 14C-Badioiabeied Fluorochemicals." It lists the proposed tests which require, or would be s~mplifie~ by, using radiolabeled fluorochemlcals. The section addresses test priorities, the preferred placement of the ra~olabel on the fluorochemical, an~ the importance of having rad~olabele4 mster~al for each recommended test. The appendix also references the location of the proposed test in the report. or Appendix IV: Article from the Chemical Re@ulation Re~orter showing the importance o" structure activity relationships to the U.S. EPA chemical assessment program. 22557733..00000088 [-- 3MA10065470 ononzs 3M_MN00000025 a -- 5 -3- 1. mINmTRRoODDcUCTTIIOONN VIL TINTIALY A. Backaround A. TnBThahveecikcgEEornnnQvvsuiie~rrondontnam mleenntttaealsltLLdaaabbtooarraaottnoorryyIhhaaFssluaoarocccoohnnessmiiiddceeacrlaasbb.llee aTamhmoiousunntwtorookff CCCce{ooooPnmnnaavrsmsmitriieeossrrnttcc1)sm siiaaellpp"nrrFtCiiCaahthmmleeeaammrrteiiioiccfllsaayytllFssiodoffsaoDDtasreiinonvvvvcoiiiinhsscreiiooaoo3nnHinnemceeapfplnnlrruttsoooeaddrlluuoccscttssthsscucedrryeeeam'eenn.dinndciianna8lggspp. rrtteeeevvsTstiithsoosiuusssoonnwork (Part I) "Fate of Fluorochemicals" study*. zmNSHooeUellabaerejlclceyyuuclltaaeaarzdllllvwtCeeoCoiiomeggmnmhhmvteteirrrccffoiillnaauumllooerrnCoCothcchahheeleesmnmiiiiccsccaacaallrllsseeppDnDrriiioovnvddigiuusscciisttootssnnudihhlleaaiisvvqq.eeuuiiddbbeeIeenaannnndmdoslltoowv CcsEaaulsbsueejcsesr,c,otcetthhdheeenssiteecoasslettsnuuvddwiiihreeiosscnhmeddneectttaeauesrlremmiisnnaceecrddueteeni1))inlgetthhteeshtacculdooiintneyccsee.nntttorraafIttniiisoohmnnossstooff pP(Tf(oo9e9lrr6a6utto-dohhiiirrelooo..ynnc;hsoo~eff"Cmga5in)0cdtt)ahh;;ele3s) pp22))rwrfohoodridllucuaahccbbsttooevrrceaaattrtuthhesoaaodettrryyafmmBcliiBOuiccOtDorrDer/oo/oCooCcOrrOlhgDgDeeaatnnnthtiiieeacsssslemttailsssstyddpccereaetottnnodeeurrddfcmseeitiiggssnnhrr,eeaaddddeetthhee msNrieeiscartdraeioblblyit;ear)leaatnbBdmlieoonaa3t)ssssmaafiyyoc:srroddsoeeerwttgeeearrrnemmidiisnnmeefsddl.uoStrhhoee~hlleeemvvleecllassl vwhhpiircochdhuciitnmshh,iisbiict waste treatment m~croorganisms. wVS!IEeennrreeSttheheeddlooenncPpeeatarertd:ttoo eI iffusuusotrtrrututoddhhcyyeeh,,rronmemeivovoeararalelstuusaa.eettexxe(ttee1nnt:tshsh5eeii:vv3eeee1nnvvlliiaarrDbbaooootnnrramma:aeettnnofottrrraayoylln sssettttfuuhffdidseeiicecetstsss SostEifttnhhiiuussgdssryyeepplarraaetrreeceeesstreeenndssttuduemmftmmrrlaaaeeuirrppolioiorzrzroteetcaddsherrmbeieiinanSfcceeaTkrTrlageaesrbbnnollccueeee{nss1d,i1,,a2in,nid3daan)nnf.dddoSirimssttachchDeteuuaistsmoFassnaaeeisisfnnrfoottrmbbhhooeetdssttyeeyhheiosdodfafaFtatatae ooiffn gFHrlueuoaortroeocrchhedenemiticacaialllssasSSttuubddayyckgFPraaorruttndI1I..information for the Fate TTPBLhhriUeeot3ggEmmrrSaaaaesmjjnooerrPbnaairrgscteeeannleeIIsrraaaallpnnaddrfffooiiottnnrdhhdnieieenrnrdggssffoiivooeeeffllrddtthhataeenhn~deFF1aallttaaseebbtoooorrffaattthoFFoerrellysyuuoorrsysooettccauurhhddseieimemesisiactceaaoorllnnss fluorochemicals performed over the last three years are: 1. TTFFthhelieesuvioomtmrrotooosasccntthhceeeemme,niinvccviaaicrllrososomnnpmmahheeraannevvttedeaallsstlloooyymmeetsshiiecciggoornnmmiimmffoohniinyccdaarccnnohhttgaaerrnaaiissccottfeettrrhhiieoessitittrrhiieccgrgssrr..eeaatteerr Bhhbrtlaaiheilolossococighghseaeetsnnmnatiinacccbaaaaeinnl,llaa,,lliootcggyaaossnnm,,ddpaapprpptthooeheo~aotrtddosoeetccggohhrrteeaaotnmddhiiaaeeccttxiaaiitrllooennnhdmymedettcrchhthohorraagoonneuutiignghshshemmossrcc..hheeommtiihSScceooaarmmllee,, ooff Tntnhhooiinnessfflluussoottrraaiibbnniiaallttiieett4ydy pap1soporprtedtiauioreonsnsstotooofftehoxfftlleiuunnoodhrreoorcctehohneetmntihieccsaatllrenmmogoltleehccuuollfeess.t.he This stability is due to the inherent strength of the * ThFhieelorEEonncvvhiierrnoonnimmceeonnlttsaallStuLLdaaybboorrFaaattrooerryyI ccfoornnoddnuucc1tt3ee7dd6 ttthhheeeouTFsaahttee 1oo9ff79. Four LtLfFfRPelllcuuuhooo33nrr8r8io04ooc44ccca--hhhl44eee))nmmi~~rccwwceeaeeaplrlrloeesrcppsrreeSooxtxddwauauuedmmcrc~iiettnnsseePdwdarr((itiEiEtnnAAtITIessnoo88f:mm00re00eo72m11Tdd,,hee1tet9aaLI7iiR6Rpllre55ts6a6ahe22nnrn55ddo,t.ugsshcpececrvcveoe1rpr977aoa799ls9l55a.-1l223333M,,Fouaarnndd oEEgtrfnneeevcvffihieetrnrrrhoieoeecnnnnammccfleeeeonnssuttsraanmellacipnhnoyeyrLlmtaaisbcsccfoeoawrrleaattrtthheopoeerrsrsoyewyedruiwUeectreaattoocrsettlineeil.:ee(crrc1oo:mTm3ttph,pee3eercc)sehn.hhnpieeirinncecssasaAiilelnvvnaeetlssytetpurrlirdeecoilppaepooslsorr'.sttassl omoTnnhee tthhrreeee VeodofirlfkfteihaecnulEftoceiueresT-coT-h-weOhm3Rii.ccEhalWnoEpwrEodhuacvetssbee(eeinn,2,sso3or)lb.veedd"An((4a48l0,y5t)i-cS-asEltyymmiicesd tehnee , work on cc 795-23. S3MMAAT100008655447711 _MNODDO0E2S. 3M_MN00000C26 22557733..00000099 ls cacbon-tluoeine bondeend 12 peov7asiy.enhanced byTtheAL carbon-fluorine bond and is probably enhanced by the Creropnabioris oth Far tLuEETRINY SONMICRS UY hydrophobicity o the perfluocinated portions of 3M Hliceetentelat ont: Frdcopmenicity Gosia be fluorochemlcalso This hydrophoblcity wou~d be SRREe E Sl IE a RenEE NheS HSeesrht rryees ls ininized. > ex~--ected to repel water from the fluorochemical molecules so that hydrolysis and degradation by enzymes is minimized. 3. Wout 3 Eluorachemteals exhib lov orders of ~ost 3M fluorochemicals exhibit low orders of Et Loa ergata Seek acute ane toxicity to aquatic organisms in both acute and Ror ote Suractants. subchronic tests. Some f/uorochemical surfactantso Fores Seve bain Sound's be emtEticee: however, have been found to be exceptions. ERIS ie angie, a noseiatesy tekte co EAI 80021, for example, was moderately toxic to Erinana tintore la ChLiAtal Thtacsinst Sosdrese). fathea~ minnows in oritical llfe-stage studies(6). EN mead Tovaeas Hara ie SH It should be noted, however, that a majority of ont RS Suttatene She commonly used nonfluorinate~ surfactants are also SRA a moderately toxic in acute aquatic tests (7). 3. The fluorochamicnl alcool. Ln 3ekd-d; has vary lov The fluorochemlcal alcohol, LR 3844-4, has very low LEE nat nT water solubility, a high octanol-water partition SE erkiI tnea maanIy SI Se coefficient, an~ tends to concentrate in ~he lipid portions of fish(8,9). 4. Segression snalysis of sxperiomntal soil sorption Regression analysis of experimental soil Sorption STERLCIL SRI Sey coefficients and water solubilities of four 3M eacheniI TE theat Hho Fafanecats fluorochemicals shows that these two parameters LE Ch Ie correlate well with the same regression equation SEES or hanFhuee naced pesaies 18). "HELL derived for nonfluorinated organlcs(I0). This fades TRL ucturaceiviey suggests that seme of the classic structure-actlvity BIAS nin ree er ale a relatlonsbips for physical properties also may be SRR SRL applicable to fluorochemi=als. 5. Prolinoecy fiela stustes at Decatur dusonstcated Preliminary field studies at Decatur ~emonstrated He es, Lame Sn that the soil environmental compartment receiues the HE Tor highest concentration of fluorochemicals from the SELLn application of wastewater treatment sludge. A FET ST A I oolffabooorrrggaaatnoniricyt affnllvauoloryrisininese((1ls1lhs,o11w32e))d." sluIIdnngeccoomntppoaarrciiosanootnna,.in 730 ppm Luau Catt entering the Memneries Avie in fluorochemicals entering t~e Tennessee River in Sastieater CHEAT SS 3S ne wastewater effluent were present at 10.9 ppm organic HITE Te SED Belted TENN fluorine, but the volume of the effluent is 200 times ALi that of the sludge {13). +. semsining Bizemments Concerns B. Remaining Environmental Concerns nagor anvionsentl questions xbich vase not sdesessed Ma~or environmental questions which were not addressed frie aa ee a MR during the Fate of Fluorochemicals Study Part I or which sirname have surfaced since 1979, include: 1. What are the environmental fate and effects of What are the environmental fate and effects of tL fluorochemical polymers? 2. what ta che epplicabiiny of sar (scructure Activity What is the applicability of SAR (Structure Activity Relationship) estimation techniques to Hanan fluorochemicals? aunroossi2 3MA10065472 auoso? 3M_MN00000027 22557733..00001100 J = i-- mWaE ASmSSmRESSaUmeeOT aTTmoaemmAL |Ca17SO2/i(Et) Eros aoe PHYSICAL PROPERTIES (R~ Tem~) SoAouloes solub., i~/l: ~080 Ya~ Press.: sima Soil ~C: In~clusl~ >3~10~ 5Unknown(l) 17 .Inconclusive 1221 SH0.0~. 0.16 =6.-7 Unkn~vn (e) 2 ry No ~ob I I 11-/ Hydr. ~oEAI 8002t In Pho~oChem I ca I , In solution: adsarbs<l to soil: Nocia[b) (T|/~-77 hrs.) Hone(b) DFI ~-12.3 end for 24 hrs. Shako f leak : hrS. =w==EF~'ECTS a FISh, ~s-4-1r, Fathaod: sats Bluegill: LC~O, mg/I, TrouT: = None 3.~ ~ II RAEI Fethead ~g-fry l.g Ru$1due Der.~tur effluent. None (2 1/2 ~m~) a. Hone Probably none or None es 17-day) Inconclusive Fresiy onal) Pro~lbly no~e(e) "766 uo>100 SE >O.IIll soos >.~013 In lob s~udJes fish times aci~eous oat. Fish pla~ In eft luen~ e~u~ fated 7 LE - all Eo Cell count: Nicroblal, mg/l: rg No In/Hbltio~ Of ac~'lvotm:l sludge ea" et 4000 m,~l sn.ate 7~ 4~ NO Inhlbltloe of a~. sludge PeSo fo mgr lO(~O mg/I NO offec?~n at 0,1 ~mg/I(d) - men| e~ 1200 - ~J/l EEE re) S~Jm distills. (b| S~udy done In OI ~ater Egere a~ >300 nm J-- 3MA10065473 3M_MN00000028 22557733..00001111 6 ILITHEDENrIT~IIIAALL 3. hat 1s the fate of Flsorocheicals in soil systems? 4. 4. WW Ehohaatrteaaairreelattthiheec cccnhhirroiotnnoiicncmeeenfEtffaeelccttssconooncnenbbitioortataatioffrnrosom?m eexxppoossuurree to reallstic environmental concentrations? BnTTnherehieoeissddgeeeddappsr~oaaopnntpoddoossaoaoalduuldttrleelieixnxsnppesellsosorrteehaassesttheaahrr~reeeeieaaessss--yuyeewewsahahreerrwreeiSStyyhffssuiuttnerretmtmh8ahaeteBtirrioccdsse~tttaeuuetddssyyttibinun~igdgssget. pTSGTtoorhlhoeeugseseoreenrnasosmufcfuuruhreerertottnhhittheehcaereadrid-llssroctoetnuounsgdnsdgti--ieteattehssierrnemaisaaenrregeeennisvpnnvsireeiurroecoeodddnsnueem cmddtewesnssni.toottahalitltnhhssaaataatffm ee33Mt0toyydcceooaasfnnft ictosntinie budget, continue its fluorochemicsl-contatning products, TTffFlhholueerioorerrroemeocifcfhrrzhaeaeocm cnmittmiococearranylyltssannlaiiadtetuuTenrarn teegituiflf((iiaieis.t.e siseo..n,tthshe.ppemeserSrsnaasicssisslttippeedooninttcnceegeenn)t)tifiaouoalrfflthcceaarnncditidseaasttteiesnsg oCC rrfeFooeoqnqrntuJurtaeii=ropronelaelvmnmirA A'eeocsn~cnttttm ,ssC, heetUutnhmhnnteiedadceelaErErluruerliraooCgvwppoueeenslataarnnsstoiuuolCCccnohhomsLmm4aa,uvssmn.iunitttnhchieiletueiesdTTs:io'onxxgiSSicci~xfxutSSthhruutbbhAAssent~taearennnndcctdeseemesssentnitnt,,g or Japan's Chemical Control Law. . zining Co TTwSwihhiiaeettphhsssettffau'uiiddeeyltyliddswweiiss.llttlluusd"iibbSeeeepssecccoorrinneefddqiqcuuuucciittrrieeiitdnneggmsoovvtteeahhrrceeegaagrgrieettvaahhettrrneeeesseetpt--ryyieesaaoazmrrrooiuutnnppytteerriioocooffaddt,,ings wfefhrlrioaocnmphse1IdtthtoeotimpIIerIi.Iogr~iaSnnspdde~iwccciiaalfttli~icnngpgriotiigemarmppesoosrrstt~.raaenncceegivaaennndd pttrhhieeorooirrtedyaerrraiitnnings whlch ~he program will progress. b. cCoosts__t__s_s TShhEeetimttaoottcaaelld Cfcooossttbeooffthtrtheheee fssottuuddfyyouroovveemrranttyhheeearttshhrree(ewa--pyypeeroaaxrr.ppeerriioodd iiss st3e$teee30sscs0t0ttt0i,i,m0o0tat0n0yyt00ppe))eed(..v)aat.nnoddFFbooTrerpparrbiiaatlooherrssriiueuttem1myym3a,..atrroyyassleefseellooiiusTrsTtataiibinbmnlnlagegnetheoyo114f4feasrpupiimsrnrncooajjtt(reehhaycceep.ttpeerssddouuixmsm.mcmcoaaoassrrttyysa bbyy ssseccchhteeiddouunllee (bbVyy). qquuaaTrrattbeleerr oo1ff5,pprraoolpspooosseeAddn wwtoohrrekksauanmnddmarccyoo,ssttss~..s a 22557733..00001122 u3MatA010008655447744 a3M_M_MNoN0O0000000C02299 Ir. rLuOROCRENICAL RISK ASsESSKE--N7-T- INTIAL" II. heTFhLii~essORnssOeeCsccHttEiiMooTInnhCeALiiGnnnRttvrIrioSodrsKuoucncAeseSsasSnEtSttahShleeMENrfFTeieasskddeecrofttcoohettmhhieecapplrrsoocceeissnsseegsseneuurssaeeldd aiinnnd a3SMKssefEslusuoiornragocchhtehenemiicceaanllvssiroiinnnmeppnaatrrattliiccuurliiaascrk.. of chemicals in general and ThSSshetheehavcrittteesaovvmaamwvlleiiuunttaathhtt.iioobBnnaaTssihioocffceseqqttuuhheeeebssattseeiiinnoocvvnnlissrrqoounneoommnsneetnniwwttohhaaanalltst aailimempapcCaahdhcceettmmtiiocoocaafSflloraawweiiccllshhllpeeemmdciidocicoafailliincn the the FqeoSiunonuurvtereiessr"ruttouainoinncdondmteneseirrnosstnsati.ashbaononuodudtfTiitnhnggeEtthsnheeieoosff bcScahththhhseeeeeaimmlcicppicclrqraalooul"lpep'syesertartineetiodineennvssscirhcoeaalenmnnoam idddceraesnlctctesoooalllooimnggoiCmiricicgepaeera3lnscoeptreacbCliaa.dseeiddc on on Taminhneyeterm1maoo0ssc%ttetiroitnmasEppooErroS~ttaaGnnthtteissbbtaaisscoiihnccemqfqiueuceneasdslsttiiaoontndon tciissho::emotiWWchiiaelllrslls:aainccWghhheeeammntiieccraaal~l. hhaarmm cacSCChnooooeynnnncccceeeleennnlnntftvtterrirr?aaraattottiiniioomToonnehn6nistwvoosfiifllqlluaaeLsivcvctbhahaioreeioirmmonoaiisucctesaaolllreyappdllccsaaaatnnuuettssstsseeotsssaatnnhwh(ddaaobrrimmoaoas;tnanhiisemssaarasannsliydd:sss)ttbbooeeWchwavashenhtaxxattppbeoosseedd iinn phapsteepahnrerecyfcfioioeereranmnsm0ve:,deid1d.rtbbouunttit?oomoendand2iletent?teQeo0urrrreamddLsiieeatnnrrbieeoorttnwwaooshhtaaoaamttrnnuyssswwllteeeetrvrveeebsellhhtssosoawwncc(cammabwvuuuieecscocsehhaesdheshe.aaxaxryptpmsoao)ssHuuottcrwooceeamsnsiewveciillbhlieeeliccwttieseoeldcdclcuurrb,,e mBBRpcarlhreneooonymdcdiiuuoccccaraaeedclldaad?.nittssziooooorHrcnhoveeaewdldmmtubuqhbecycuyhehsscstuhwweii|cedlolinillnmeisencntabbtee?lm?'susddtiissDbDooobppewoosaassnneaeiindtdmrshaaweaaellnnrssddcehdohohe.rfoomwwi?c?ppellHlaaonnw1Isttsp.ssmaurttcthhheietiwoilnl be amF$bra0eeii0aaoy8nddcliioyll4n3yyc?reiIynnnataatelonnrcdatsoae~tssirhooe,etroohnnewa.:qatutceeehrrsTTe,,thhmieeiooocnfaraasnlns?sssuwooteeiihclrlaDs?ts?oestctaooDDnootsehttssbehheee.ssctteeahhheenesmqqcwciuuhecheearaesselnmttdiiiiccoopaannallssrtddisseetoogigmsroeeeanattdidiemseeess SeGdelxeexe5pgaparerdteiraarcidditnueemoessteninytoteiianatnnl.llltyotyhh.t.eehDeeareunnsFFevqOoiiurrizrteoosiinntnnptmisshaeotconnnaetttsnneccdeeebbt,,uqohttraaotosnnnneeeocostatnmmkakahnyyb`o1eosuwkk.nnaiototncwwhhseewcehttmrmhehaeaeanjtdjtioocrraaailcrctyohhoueeutmmteiiesccsaallooff oSTpdlxoexaaigribbdrsGooaiiirrdznzaaaieetttidoaoii?rrrotyyni.oCCctnaaoe.nnssttDssoiiettsttboobiliotoesdsvvseaapgglthrruuoaaatadctoceae~s,.egttroohharfeedecppc?urarnnoobbaaIiIbbsttiillhhiiityuteddyyrccooholloefyfymzzieecee?saaacclhhlTyThohoefefrreetthheaeassrreeee AApLoonsfugsulililnlbil1claiisntsttiebseoo.ff spphooossrsstiiebbnlleeed qsiuuheessvttoiioonnwsseveJf:ss qquuTiiFttreest,ioonnts@a,,stibbnuugtt ttishheedone lthSIinnee0e"ssnEttgahsstne"hkpooperfeccadrdnffeFeoorcarrlblumebyyneeddppsorrhfoooiipgrnnrrtddteeeiiesrnccssaeataiisdttoeoenni(whnIhsissoiot.cec~,hhotthheatwttttiaeeeysssrtttt.sshheoefaarrFrreesieeersvsqunnetvlooi,ettttnsstsatipoopesffppslrrtooittppnhhtergreeiisastffkttsiiienerrgssdttoiinnne sSCtsIehcnheeehseeteamnttneenhhcsxaa)e)ttt.,.ccroeo"TrARruEtstenaad`wlippennorrfoooSppitieenthnrr0eeettsrsiitteeshssattsee(ssooittffa.ase.a3c,aahrcecceemthhiieecemimiarininlcacaaapopllprpGrrAooaasTpprrerreeqiiuTaaeeeettnlpleetuiu.:icicailildydaaFFttaooteerrnedsds,,tinvwgee ccaann cclioonmmstppoallneeccteeec,llyy itddfiieeaggwrrneaaddtfeeie,,nadttshhteehrraeet aiiss clThiiekmnieecrlayyl nnoowilnnleeeedsraStpooidplpeyercfiaoonrr4nm TTTbtThhheeiieesrcsteas'scseceisccuTiosoomnnauddlbbyyatvwteaiachuoyhysinnitnioosgffqtueest"t"thshisistit.ncrnuninucieictnnntaggturireseaatsLalaiiccsusttsttiievvooiifftttygyccshhrraeeeeymmlliiaecctttaahiillaootnnqqssuhuCneiehispessstmst"ii:icooann((lssSSsAAooRR)rr). wFCTpcahhhe0yiyyl7,sisaiicccuSiieapsht1loon',ninaniaatttpnnehhsddeec,hmmnbBoioiialqogleulieceooccuggaulirlslaccceraapillreenssaittppriirrracsuooctctppttseeuurrrrrttueeeii:sl.eeeessvatnoddIItfeepspewavpeeneyr.ndod,puutenhnrdadiittenneircesasacstthaoeppnnmrrfdsieercddoainittlcchh,ietetasashbebeellee SFesrfitrrerrrveleiuiqaqccrtuuttoieeuononnrrsntteeesll..hhyyciapbblsMyyT,hiibbisswoooettnhhssccciiaaiieenmnnnnaddcicupueyesrsetetirdriisMiyssctbobaenneiddirnnegglrreeeuvuggssauuenelldtdaattFmoopoorrrrryyoeepebbaroaontnddddiiieeesssmpoorsfiieennrom the environmental risk analysis. WkI006475 3MA10065,475 3SM__MMNNOO0000000%0S3E0 22557733..00001133 -e- 2 CITA S oSSSethbtsrsrsucueerccrritutvutuaaerrtteeiiootnna ahsscectsteiooirvrv.siitbttty hiyhee erorroe vreraelleattatititiiccoo iana onlsnlsshcohcoiifopnpnscstcehepsaeptcortseers,i, eddseerEriqaigvvurueeaeadtdtitioohffrnnerossnomnw wLre eurimem idptttitperetinrinoiccaa ftolol describe these observations or theories are then used to Predict properties of untested chemicals falling within the predict properties o untested chemicals falling w~thin the Ehiernucttuecnstied Titnoitvsaroifattehesnsdystreenf.ineAdtdhietiroenlaaltiocnheenmiipcea.ls are structural Zimits of the system, Additional chemicals are then tested to validate and refine the relationships, TSTffeherrsasootmctnsesvssaaiaitnnmmiddppollneeoosbb.sslleeaarrbbvvooFaarrittaaeiittldoooonnrrsysystmmuuueedssasieesdsdeusurrfineenamsreeeeennnnttvvsssiirrroottenoonammleef-fnnivitteeoaallrldldidststeettlssuuuttddxssiiueecsaasynnddrcoaarnnggee oeaSSShnhbnn"asvveiiiirrPrmnvoroppanneootmmdrr{eeittonncaantttnnsaatit.ilonoospspscppFiioowieerrienntttltthuudiinnsslistttttitssayyu,,ldsieeexbxbssuiuittbssttsasseriirennvttaoatotchhieebbroaaenccccaskkaalss-eoeuuwnppooorff3llldaabbfFuolonllruriuuaoqaxsrtututooeorocrrychyyfrelfemaottslsreeicssscattalssossf,, paplaprArnadpSoobropoparrrrpiaaiirstteseaoottdlrraelyyrrcyotymflseoecSwanahhssseaeuumtarriwelecimantetleehhnsnnel.ttfsseien"glTgvdmih~ieevvreeoossncbcssooeaenamnrtbcmsviiauuannlcctaahhictoliinomoRnsonnoprcaeeoco0nft2ccaofo2Fnineuvevaueiliinlndnlieccyg'iiuiannennHggdaac-l-oarss isof oF appralsal not. of ~hat ~he environmental impact really is--or is IcIGSamaamnpnupotorlrhhtnteeagalln'npptotflla~yyln,,nSlitmRrpp~iurrzzcoueedtd,,eeunnrttabbluulttttyeennsseerttvveiieenlngrargteoeoedffnnttiincnrrheeeevewmlliyyccchhaeeeellmlmsilii:mccmlaailnlnsasaCttaeeraa,e,sstutftflhuhuetecyuyuprrleeeeavnvonolilvnvege nZacctonaaeennnssucwteeiyyerrnir1nge1lbb8daaoasnfsdiaaiccstpBpqqrUrruLuooueLcppesdteestrurtiriaooaaannlnnbssldeaysiacacsboobrommeouppltutlalotteeettmtthdeeahekeectChcceaehhspsmetreeimiiemcinndiacggiclacasltppl.irrooooofnggfsrCraaaiim~~ssmebm mfoetteuudhhd~tiaaiattatptteewwlh1eia1ln1lning Ecbeeohhnaacvveiirooner anooffd ssb~uiminl~idllaarra ccbhhaeesmmiiisccaatlloss mpparrkooedduupccreeedsdiciinntiottnhhese affbuutoruuorrtee.:the fStITneehssetttthhreeerelscceTuaatslsreetas"ootffStooafEmddllpaauuitcooeeerrsooccgshhiievevemneiiccrraai~llssssee,, tossttrcruoucnctctueerrranell to concern foccroonnessniivddieerrroaanttmiieoonnntssalaanndd for environmental sa=fetyFFE.loiubvaooorFrnooocrchfheaeemynxiiacmcbapaelllessL:ianarrkeeedhhiaanllotoggheeennaatmteiednddsoorroggafanniiTccessquaainnsddtorffsoorrvittthhhiiss EFcrrheRoalStsoRoirIneinnnasamttateyiadnbseatnnhdaell`pnbBekrraeootdmniini(ranaattegteddh.eccmooPimCmBnpp,dOosuunnPddoBssfB, rttDhheOaagTttu.lahhataevovrerees)cc:waaiuutsshee~d problems in the pas~ (e.g., PCB, PB8, DDT, etc.). | = FFhlieuunoorroeechslhhoeermniiinecaaatliesss"aarraeendeevvbeernnomnimoonrraeetedrreessciihssettmaainnctatlstt:oo ddeeggrraaddaattiioonn TTBhheeerssaeeistthccaaoonnnnccceeec,rrhnnlsssocrgeigiiunvvmaeeutleadrrtiiissaeoenndttoopbortloleemeno~stlniitatsitilmes,adatteescnhdqequmueieescscattoliitsooo.nnxssicisatbhyoouuttoftthhee pEe~lrulsooirrsootccehhneecmneii,ccaallassccuiimnnulttahhteeioeannnvviiprcoootnenmnmetenintat.ls, and ecotoxicity of TTTSthwhEeeoeossbeerTreIetaqiqusuEuooyeennsssstti.,iinootnnlssfFaiirrteeissnntttddi,,eccswoo`whnnhevccerieereercernrsstthhKeenssrrohheewoonuulllidssndarbb""aeesacmndoaskonnkeusae"swweercr((ehessdedttmrriuuffcccooattrrluurtraaa)sttll lltaaeehnnaaedsdsrtte anesaSvvntnideeadcnnb"httittuulhhaeeiaaltilypplyucyubasbinwliil~imclcilr.l.le'ashrbpeieo"3'tnM3sisnaennshehetiieoeggddwhshsitthhe!lt1seoe0evvkeehnh!saoacvvwoenencocffe~ssrcacoonouzousnnann.cdrcdederqoraanuunnnesssswvffteerrcirroohosmsnenmsiarra.ctteeagglauhuhslalan)naandtdtootrrwhwssiiettrhhe wpPhooisscsshiibblwleyy ciiannnaaccccruuersrapatotenedaactcoccuusstaahtteiisooennssc,.oncerns, questions, and 22557733..00001144 aktooesers 3MA10065476 3aMW__UMNN00%0000000303311 I RC EAT -9- Second, he propaesies of fluscocarbons sppest <a be unique. Second, the properties of fluorocarbons appear to be unique. Er rata rater alive They often do not act as other halocarbona do. In other Bach Soon EL Eo Bo worOs, the current structure ac~Ivlty relationships may or To Benue, pet a teSY PmpooaksyeenovvteerryyapLplil~tyti.tllee IPpnrroofbbalictee,mn cciotonmppaeaprrpeeedaOrswwiittthhhatootthh3ee~rr~hhlaaujloooEccoaacrrhs~eoomnnissc,,alsaanndd Fatt hg A AE are envlronmentally "sound." But since these obse:vatlons Ft A BR PER are contrary to many predictions, the hard data needed to Fre support such a contention must be of the highest quality rave Ts a ter tier ee oeeil more extensive than normalo Proper testing can strengthen rtrd i ie he the contention that our products are environmentally sound, Fak paral ig or It can enable us to identify problems as soon as pusslble. ZEoAl Sele bate Seeley probiaaneeronn a3 Fouts Showing that ouE products are envlronme~tally sound could tee hati eR have a beneficlal marketing effect, and f~n~Ing problems ele Serene ee, Tl rn Sree early can help 3M avold potentially costly environmental A En problems an~ adverse publ~c~ty. EE The potential application to new products or manufacturing tip Er Rr sr process of reliable property values and relationships shoul~ BSbmeantiener ana Ey atodmat ne Sees ene ot not be overlooked as a by-pro~uct of this type of characterization program. 22557733..00001155 unto? 3MA10065477 Smaoonsz 3M_MN00000032 FE -- 10- - oo LTIIaNTtIAsL IIl. -10COMMON CONCERNS WITM 3M FLUOROCHEMICALS ...... "--'NUAL' his section desis yi concerns thas apply to aid In This section deals with concerns that apply to all 3M Tiineassidzenals ith concaras, that uppiy to 21 fluorochemicals. It is divided into 3 parts: A, Senet ThEe TLE oe can ara Structure-Activity RelatiOnships. Presents use Of SAR and ome alumnares ote 52,0 proposes the development of further capabilitles with BeTL SRE acres fluorochemicals; B. Field studies. This subsection describes Hroreesanicylny5, stpeultdios, Tole subnaction dracri the minimal field data now avail~ble on 3M f]uorochemlcals I Du and proposes further study at and surrounding the Decatur Ee Bethonion plant site; and C. Incineration. Gives existing information De utaiint Sonee EEac tnR etsvion of IF and questions concerning the incineration of 3M nan fluorochemicals. a Sursesure nevivity petavionsbize A. Structure Activity Relationships P-- i. Background SoState-of-the-art environmental risk assessment Bearers eee pele Te preaket hy LITE oe procedures use models to predict the mobility of Le chemicals and their concentrations in various JE environmental compartments. Most of these models are ITIL SIT: emesencstin mathematical simulations of representative ee requive environmental systems and scenarios which require Sovssorrancal, ystees, ng spanatiol xhichr,eg inputs Of physical, chemical, and biochemical ee soramtiicrs properties, which include aqueous solubility, Be on eondiiotente tonos Fressure, octanol-water partition coefficient, vapor pressure, Ftp eat ef soil organic matter adsorption coefficient, and Te en Se at rcFaahtteeemssi..cal,FFiiggbuuirroeecheI1miiicllallluu,ssttrraanadtteessph0ttthheeolyyttypipeecssdeoofgframmdooavvetemimeeonnntt fren, ST eetheSitoo between environmental compartments which are Flan ASIN Th SEERA Brats. frequently modeled in risk assessment procedures. In che absence of diboratory daa, these chemoamanic In the absence of laboratorF data, these chemodynamic Tolar. tients of Litprascay fey thats sheredin properties can be estimated by structure activity fie CE A rr rr relationships (SAR). While SAR provides a quick and Shure she Beinn) economical method of estimating the chemical Sonoma) heited of, TLUTEIn0E8 Ion ne properties needed for environmental modeling, the Sremariiss fe std foe sovizonntatsd Sele 19 me applicability of existing SAR methods to the 3M line SEP 2h ne na SL eeefe he of fluorochemlcals has not been validated. The current literature ~oes not have sufficient SoEermaciint is Setene seTos Shiscing Eun poronches information to defend using existing SAR approaches ee rg EE iene with perfluorinated chemicals, so SAR applications to Shen a 3M fluorochemicals are suspect. he 0.5. Em ie actively engages in developing Bn The U.S. EPA is actively engagea in developing SAR Tit asi one io ayesenine pe, estimation-mathematical modelinq for the purpose of BSersiseino?n Smaeunaannsseisoenntimneeanstilonog Btaokr,vasatomaucrkesns ot predicting the environmental behavior of chemicals. The extent of SPA commitment to SAR was clearly illustrated in a letter from the EPA's Assistant find dnsdane tren Te mens, Administrator for Pesticides and Toxic Substances to the Department of State. In this letter, he states REEy EE EE that ph>sicochemial ~nformat~On is more readily an4 Sr Rha TL Ee more accurately developed by existing Office of Toxic aussi 3MA10065478 amonnocss 3M_MN00000033 22557733..00001166 [ -- -1- aT - #90 1 Tasetoess pethvays oF sn onset. shania fn tn STEAEORISE ~E. 1. ImporSan~ pathways of an orEani chemical in the enviroumen~ or, - - ... SSTT.RRATOA_PTAU.OS..EP_.A..U_.S._ .E. \ STRATOSPHERE STRATOSPHERE A | 2I ce R T ROP_O..PAUSE : OY # 1 TTRROOPPOOSSPPHHEREE~ DNS >"W"3 BWiAbTeElRers senso > : :y wiiifeVorIsot" ATER STRFIC PP, te GROUND WATER . W sce ws)i A A > (SEA T T J dS F E " & Va R =i fe. 3MA10065479 anno 3M_MN00000034 22557733..00001177 a IINEdMINTIAL -12substances conn (oun tative Steveture Activity Substances OSA~ (Quantitative ~t~ucture Activity a by tne hep. Binion Relationship) methodologies than by the ~PD (Ninimum BT er te ED, ni Premarket Data ~ase) measurements prescribed by the Ee Te etic! on EEC 6th Amendment (14). Additional information on HE IA) hr 1a SLE Ir eB 1 the importance of SAR to the re Appendix J ---- Since EPA can be expected to be concerned eventually fregtglng arbi 4 with the risk and hazard of fluorochemicals, they are Tren et of Se en he likely to apply data generated by these SAR methods Innate Shaner oe ee to mathematical models to predict the environmental foo rede 10 FA in rnin) fate and effects of 3M (and other) fluorochemicals. He te CE Se Since the applicability of this approach to Ee ot ror one of fluorochemicals is not validated, development of rr Rt al suffiEient scientific knowledge is necessary to TE EC identify the true risks and to refute any inaccurate Hapeiey the severisks md 12 buy risk assessment which could affect 3M pri fluorochemicals. me deveiopeent of an presicive capabilities for The development of SAR predictive capabilities for Thsotorietmuntof wh Erne SHELLS, fluorochemicals should also have utility to 3M in ee eeEE 5 the Seapya"ot areas other than environmental, e.g., 'the design of jonas ottes ansmviroraenial 11% Sopernits perfluorinated structures w~th unique properties BE Erssateton: Pectuct fecaufatlon: ax nev required for processing, product formulation, or new ene product development. 2 obsessive Objective Ihe obteceive of this proposed work vidi be to The objective of this proposed work will be to Be Siiatelsnof in met pe be, determine the applicability of SAR methods to 3M Shier, fos sliciny eete e ha fluorochemicals, and, if necessary, obtain new data omni 1 a I for SAR development. ~n this respect, two stages of fon, 0 Seselommune, In hia Tepe Doe et structure activity analysis are of primary interest: 11 she ap of equations fneereeieing I) The use of equations interrelating 2 E Tere ois properties: and BuPrImerayateat properties trom 2) The estimation of physical properties from molecular structure. For. siulins go SUssoTnicsir tre ampbieied op the SAR studies on fluorochemicals are complicated by the BL, on umreshinicals, ans conpiict remarkable differences in physical-chemical mn eens EC cuvee properties between the fl~orochemicals and other BE aeons nethee Tor sous organic chemicals. The simplest method for aqueous TIL Shing Le solubility measurement(15,1~) uses HPLC guantitation, en for ope Focolommest rie" which wilI not be effective for the fluorochemicals, Sed ML TE stirifor he ree since most 3M fluorochemlcals have no stron9 RR SE chro~ophores for ~V detection. Alternative SoS 50 SeRt RR: of teint Fhverine analytical methods, such as GC or total fluorine he analysis, will require an extraction step. A more ps HE important potential problem involves the expected ER ea Ta difficulty in getting pure samples of gic ine fluorochemlcals. suntoosse0 3MA10065480 aaeoosss 3M_MNO0000035 22557733..00001188 Iasi So seesete ho testes an . oe JIINTIAU TiTIrhanaoenepriicdacttwllvnoyyoemrniappinnhhdaacassaeseetfcsfppi.lrrcoeotippaeToo-nnhs]steta3alll-lyyPrhhsaeae~sisxeaasmnbbiieenneeseennerSSddAaeeRnssiigaSgnppnePepiddlitctteaoonttimm ioooonsnstt to to SBosoe 3:rEvaluate existing, 1uorochemicals, The phases Phase I: Evaluate existing, earmep=icically empirically ddeerriivveeds SsARR P~ PhhaatsseeiIoI1:nDDeetrroiivvfeelunoerwocSShAAeRRmicffaoolrrs.ffilsuoorroocchheemmiiccaallss 3 maser new PaEFPPhphhapaaaEslsseyeerTins1IITguwiseilxStEliesittpphrieeenrregmiictteSavAReRuurssotcnSOttmooeo3unMttNteessHfttollfuuottoshhrreeeoccctthvvaieaannmlligiiiecddauaiitlttrssyyeowovffiitthhoouutt Huge requiring method development fluorochemical samples. or getting pure p$EErSreeAL8oalRappaETteeppilirrrottoooniiccrseeeenhnsddiuiuprroTeseeEfF,,essautrnwaSaekhrhcmeniieeioccswhhotmnnoosssaatstsrreoueenfbccisoroatmsmpTiasimpalnooblactnniaeeelletdssyyds..icddtteeoeosrErEi:siexhvcvrsteeeeetrEddeiiaaampmmloeaeaasoslLttsaaiiretnneisigmgbopopaniinprrtiiiooccfyfaall BascSTnaunenasappSeeeeAbcceRnttaatcuoahihnnitiatcaiellvvnreaeadawiItt;bbsyyoecmaarawnneianembpspbbiiieercroievifyesacaaallasdniluitdboaumsmtteoteeetaytddhnhs.o.ocSddehssse,:SSduorrccewWehkhthmiiLacGovlvhhnanatlsiiirFdoeheaaqitttuvgiiiihoorrlnneeyss Tfementt Tis E physical property arguments or by a Tonbinaton measurement combination ofby of the tee: theoretical the twO. TTihisis kgfiiresstt pphhaassLeeewvtiiillillenttSeeesstttanaaopptppllaiiscctaaettriioonnpaoorffeittihhoeen S EwcerEoeleaele]nflHcatf-ttiia krlocnooniloniReyswhenhtinate ipet,p'aSuAsttRfKoinasmlt ueub,ggte1siiet'vvasweHen(esni ndeIn~ObSab,yyqIoeu5Hci nEe,Stoq1aatEuu6unesa,eot1elIri7y is/So,oowIn1nlma8Euxt,bbelt1ii rgaa9le)ispff.ttcoaoyrirrr,e othiTpPRuhtSuywriici,eseoonellffiohoiqrruueiinmedoossnnn- pct En ER i Kv and by Equation ib as a general expression crystalline solids as well as liquids. for pure I ltoong KKoowu ==R a2 dloorg BSwI y ++ CapE a ec iins SIInnerttyhhlaoeetgssaeenKioefwqnueeqa=utaiAstoioonlnossag,,. a crystalline solid Sm3SFpwp or +2i215s5hBfetftohoh(reremap-s2ma2*ee5Halll)ititaqiitunn+iiggl daC,lppooiiaannnnS tdts AAii,,nn 5",CC B, aooffnibe and siete C are constants analysis. derived from linear regression TTTS lhhiieennsseeeeaT areeqqrTuueeaaggE ttrriieeoossnnsassiiS oonnwweerraseennLaelleeyymmseppiiiissLrriiooccnnoaa.llllKhooyoyuw.ddeaesnTnvvadee.lloeoSsppwueeddtgduattsueaasi:.innggT2Th1he2e data base from which the equations were derived did not include any good analogs of 3M fluorochemicals. Subsequent publications(15,16,17,20,21) have namie banda. for shin san. in ~emonstrated a thermodynamic basis for this SAR, in en Ir ear athee by the activicy which Zq~ation i is explained by the actiy~ty SEITE Bette STIS coefficients for t~e solutes in octanol (~ o) and Cher BT IS Beaton a hate Sextthes water {Fw). For this description, we haue selected HEEI hati crestent TTIan TERERAOTO Dats He Aen the Mackay treatmentS20), @uations 2 and 3, in which ~o and ~w are expressed on a molar basis. awntcossiet 3MA10065481 wens 3M_MN00000036 22557733..00001199 Kou v 0ttfso~u- Kow, = 0.115 OL a TZINTIAL 1T5o,tih3e0see ssqoutniotn.s. A8t1nDtnh simucetptaattteiOoFr. Sw = 55.5 In these equations, /fR is the fugacity ratio for the pure solute to the liquid reference state (f/fR = I for liquids). The fugaulty of crytslllne solids is less than I. Its f/fR ratio can be estimated by EERE alain nade, means of its melting point. Combining Equations 2 FRR Gir, SE ney and 3 yields Equation 4 for pure liquid solutes. 109 Xow = -10 Sy ~log 16 + 103 Ko " log Kow = -log Sw -log ~ log TThhee MMoo iinn tthhiiss eeqquuaattiioonn iiss tthhee mmoollaarriittyy ooff ooccttasnnooll iinn mL gin itself (6.36 moles/flier}. A ------ If ~o remains constant, then a log ~ow vs. log Sw correlation, as given by Equation is, will have a slope, A, equal to -I, which empirical regression analysis on nonfluorochemicals confirms. The melting point term in Equation Ib accounts for the difference in fugacitles of the solute as a solid and as a liquid (the defined reference state). Any series of ffimenien axprensionsof Sapatien 1, aires, solutes where ~'o varies will not yield the linear regression expressions of Equation i. since 3M fluorochemica!s are not miscible with octanol, Brees imeapiSd do gletin nonideal behavior and a wi~e vacation in their octanol activity coefficients, ~o, can be expected. These arguments ultimately predict that the existing SAR defined by Equation i will not apply to 3M fluorochemicals. A Amidon and Williams offered Equation 4a as a general relationship for relating aqueous solubility to octanol/water partition coefficient (22). They derived th~s equation from thermodynamic relationships for the following sequence: solid melted to supercooled liquid; supercooled liquid dissolve~ to yield an octanol solution~ solute partitioned from octanOl solution into aqueous solution. This equation uses the solubility parameter, ~, for the organic solute as a means of estimating its activity in octanol. Since this equation might be valid for nonionic fluorochemicais, it should be tested. -7.3xi0-4 (V2 (i0.3-~) o In this eguation,~SF is the entropy of fusion, V2 is the molar volume and ~ is the Hildebran4 solubility parameter for the substitute. anssas2 3MA10065482 noon? 3M_MNOOeO0037 22557733..00002200 as =r P'en E"NNTTI;AAYL' 7 41510 the need for pure lsocochenical izomecs and To avoid the need for pure fluorochemical isomers and Sethads development This sce precedsisics to che methods development that are prerequisite to the Sher lr FIR: NCAT IE Ce hd a direct study of the relationship between Kow ~nd SW for Eludrocturiests. an sisecnacive soptorch IF foc fluorochemicals, an alternative approach xs Froponed. This seproben vill sxsrine srasatic proposed. This approach will examine aromatic Boe ian pare AEbootey batvesn eater son hydrocarbon partitioning between water and E HueItunT tct Sola vers ny meeans sof EosAstDig.n 5. which fluorochemical solvents by means of Equation 5, which can be derived by the Hackay approach(20,21}. 108 Key = ion (2/2m15umiVonp + deg Kp log KFW = -log (f/fB)Sw-lo9 ~ + log MF (5 Rare, py 3 the Eiuorochenient colvent-vater Rere, E~W is the fluoroehemical solvent-water PRT SE TI a Ty partition coefficient, ~F is the solute activity Boren Tn the Hiorbonemient Fotvent and Br 1s coefficient in the fluorochemlcal solvent, and H~ is a, oe Tn nesetenion Sapeent Ir ieked. the molarity of the fluorochemical solvent in itself. Sherine eatnet ar ew vy aresaion A nonlinear relationship~for KFW vs. Sw regression Sosa Re Cinte thee Fy for omtic hystocetbons would be evidence that ~F for aromatic hydrocarbons T3 noc be Canteant. "Te: varies for'a series at would not be constant. If _~F varies for a series of Fr biacston: soietes, ines 10" for 3pet Sioscoshesions hydrocarbon solutes, then ~'o for a perfluorochemical ee ogous ca che Eluarochential otvent 1b series analogous to the fluorochemica/ solvent is p SifeckesSotA iie vary. H This vouii s sepEose. ihe uorbcnemice15r1s expected to also vary. This would support the concept that Equation i will not be valid for 3M fluorochemlcels(23}. Tuo procedures for km seasuresant are hero Two procedures for KFW measurement are being fred prea ig ais hogtiei J considered. They are the standard shake flask method SSR pTraaeis noF,hIo nationCal aFacreeeonf tSiarhserees ETE2 Hl He ntetenital sotvents Seiected or preferably the new column generator technique developed by the National Bureau of Standards (15,16,17). The f!uorcchemical solvents selected Shou1e probide's, Sepeereiie SoLitety af the bebevicr should provide a reasonable estimate of the behavior roan Shoes ringing From of 3H fluorochemical types ranging from Huotocheicat nets Hlauics oa Fuorogpenical fluorochemical inert llguids tc fluorochemical Ee re ties ashe pretenses alcohols. We have selected as the preliminary Saraioats sotvens: 1) feceivorosciner 4] candidate solvents: l) perfluorooctane; 2) Se Sha cd hubrceatorer tion Dione l,l,2,2-tetrahydroperfluorooctanol from DuPont EON an 3] MES FORE slgnhe] (LR Thet-). (C6FI3C2H4OH)~ and 3) N-Et FOiE alcohol (LR 3844-4), EP Ae elotni which iS a solid. This series of fluorochemicels, Touuer: does mot coves Ehiorecheniets hich lorie however, does not c~ver fluorochemicals which ionize ater Cah aE ERY hota Flr ensurenent in water, such as EAI 80021. Either measurement pO i lee technique (shake flask or generator column) could be Spied to the Tuguls cFioechenicatss bo the reli, applied to the liquid fluorochemicals, but the solid, PE Lon Tanta Te enbeatsr Shion LR 3844-4, wou~d require the generator column Soptasdh: He Wit] Setest spometis myscocathans from approach. We will select aromatic hydrocarbons from Ee ato Toor EL Naor Bares Table 2, This table comes from the National Bureau pti esi Bi dl of Standards studies of octanol-water partitioning S Sho aL aeencIe:solsbiieT g: Ce he expecEtTsLo Shoots Shout 10 and aqueous solubility. We expect to choose about i~ solutes, base~ upon statistical needs. 2573.0021 2573.0021 auktoossies 3MA10065483 0000038 3M_MN00000038 EET TABLE 2* ~ ness ~UJEi'LIa TZr~b~ om ooncrwAeN~cm La/~rIT~ e in een SHAY T Tr E TE E TT Ar~ma~l I<y~Pocart~n$ ve . io pe aw? Lace a. wari Ed an ee FE Sa alt ale) alt E --Ce -- TTT as ra rd TE EE(f) ~SC~ in~ Leo. REE (g) ~c~y e~ ~.. 198o. 6 te vers te 8g ramet ""Ffrroomm NNaattiioonnaall BBuurreeaauu ooff Standards (15). noesas 3MA10065484 wns 3M_MN00000039 22557733..00002222 TELE 2 (Continued) yy. TABLE 2 (Continued) ee wrle rts emse INT me me ee me mm _--e e emrytony --T pr ------ E Ft L lBt _T ITTE E-- lT i -- a a e mT o Tg I r PRP EIe TT [RE SETI", auatonsseas 3MA10065485 awunanoooceo 3M_MNO0000040 22557733..00002233 he following "tee cable summarizes tBhe aNntCicOipNaEteRsISSEENNTITALIAL TBoarsabeent:log veo The following scheduling and sempour Sot the table summarizes manpower for the ack pistons the anticipated work proposed tn in sPuhnaesteio!n.- sanshoues s~aOntcutpiotnise so-s0 ~an-houts AA Sneenavtaduiyplyottpitiiccmmaaelelntm meetthhoodd 50-80 S00 SSdTyyaesstnvetgemeelopttfm eoissnesetniiintnnggy ana and 50-70 sore Psfaaroarcontetgitezeriioofnntionsmrdeeissenssgauucsrheemmseeonnlttvssentvu5sse0i-i7nng0 spproxieately approximately ten ten E1R) Restiaorroesctane 125-200 solutes or each solvent: 1) Perfluorooctane 125-200 a2| pBerliEoroaciantt 1,1,2,2-tetrahydro- perfluorooctanol 1210000s--115500 3) TLoRta3l844p-h4ase 1 a704-sie0r00 4 msTeotanlr Phase I 445-670 PAAsP Phssuhybasedssioeetcsslacctlr rruieisbnbcetehdeanfisaaa chbcaoot:vvoeer,,praonSSs paAAeRlRrytsraiiefesfesesrfsso(r3tt4voeo:s5tbbooi5ettm:hha3t0)ami7.otn7lgeeccauunllaaarr TPIppcaEBhohhpoEyTyyprieessrriieioekccacalecaatacaillhlhta--e-einncccssothhhneesewvmnmiiseiiiiliqicciclsusaaaatllltCsriheetpopIpfqornnorruuoeskoioipprrpeeeeesewrhrrehtittiasaiaiicnheeeht.dtsssaaaettr(dsae((1l1T28EabFb84:Etea,e,,4ess1p28ee95e:,t1,eoo52w12sff1o0.~t,,3i2o3Ll28n81raa7--vb]33smaoT97norrah1}raanae1.ediityooeerysyBmsoatthh henies to vieia the BAR measurements to which standard are applied to yiel~ the SAR. regression analyses hoTSohbSeeesennroovvbbiijajceteiccipottouniintevvseeedssTinnootfhPnahisanttsehh.eiitssheI1pphhaaSaannkssdeeesdaewvviilLleliillittseesddrrreeaaeppttneeuutnnrr~deeWisFurLopeoLvovninioeiwwrtts.hcheeiusI1et6 oEeecisosnntaeasitrtnmatatannitittcipnassinesgpaoftoepreretadroohfennlteeuhuoaabttrootrorocrthhmmhoaeoeounmrrteiSecAnsaARkylleyydeafFhvpErraehaaAlygssosmewipeleaemnncf1etetar-nltt-sscuhurhwbbeeeisrnrmlttsiiliioccttraauvielleen;nncttluadneg moE%eprarkoisEphnoegirltiineoC ntsrti,gecarpnpsrT iruococppheemrraaR ttstyyteRrocSwoo,rsSirorereSelpwl,atttiiioocaonnln~oscSm,oveeafpstboufotcrtihhceipsesarnnssetse,sh~uoorpwKoeoc,ovsos:v.vse.!Su ThSTSlhwiiel.etieeosrrsaatttttuuuuddsrtyyee,wwii"atllnVnlldaapggoHfaarrottorhhpmererbrwwtiisttaauhhvvtiiaaennii,llsa3nbbMcollteeonannddsaattltthhaeeeusaiaJinnqqauuresttoohhupesesrsrtition SSscfFeoolielesuufufsoeibfirreiioroliccceiihtnoteeeenynmnnt,tiit,,ccsaavltva"assaipnh.;idoairssopWWboiehriaeelnns-aswuduanpaereteteces,eeratssosioppaacaorrtr1ryy1att,:1initoeilillioo-naannwbbaosotrhrcceaeoaortncetoegfrerpfFgyyailerce.tikieetnnittIotnooffix aamScneEctaSIauisSercuEtairapetpeEmeamEttei1ean3ttd'thhstaaanntTewhaiiiItlnnSleepsskrubovceeoihvnToimhomBaesueednssasiescsauusstoirpitaeeoumstdfeteiu~nneslits.tlcsshssinwwiiiionnllccrth~leeiesbbaShbetgtaattspemmesmoes.prtpiteeinssa~twwteiilli)ls SbSieEsEoommmNaeedrtSess ErtSoaatthIhuneeseSrr StttehhosaeetnncopcErrhecoerodmeuiccScttaesdlisowwthwhihichichohmsaeerersexsi"smmtiixrttauserreesseingOolFfe . structural and molecular weight isomers. wat0085485 3MA10065486 Su_uNo00000st 3M_MN00000041 22657733..00002244 privy su 5 EINMS C~NE IDENTIAL. C CpfElouEuorbiorrierreireolsoclaasnhhteteieidom noniniisesncsa]vw tlihleipBllllroiotctephheceeersnrnsiticeebbsusee.r,e=naSacodvofmeem oprapbbtaaoeirtttpiwnuhggeee.eernntthhteyemsmpseeessawsw.siuuitcotrhheefddtthhoossee CpoSSEcourioCrgabrTarUnleiensiLAalihaccLetsTidccoYooonnmmiEnspsapoohyouueatuhnTRrndeeeapdstas.dr.ltnihoitonoiensvFEreeiaeaxnoaatdsosomuFpfprCAielovaevneasasttppforooOofirr~1c22ipro6r~ee7eetr:hnelleetseesvosvsrafbuauyrnntryeaettpBqeuaippasenpnuuogadvbutotlsiiwwsifeahametetmeedeerrt ction costs 1Clent ednevCeolonti Tetan LensntanHicastotion solubility by Amldon and Anlk ); O aqueous solubility and partition coefficient by Banerjee et al (21]I and o partition coefficient and biosorption Bpaarritxtologne 598coef~icien~ pee 8eveloped by Steen and cSSIIhfhfoeemccmnooooegrrdmzryneenailatnaamhtttieiicaoonfnphsvsraolpbbroeeeprttetvw]dieeeeesrnestoott~rihhmeeaftpplihhuoyyonesriioccscnaphellpenrmoclcshchseaehnlmisiccwaaiatllrlea~nnbe~e dsaBSfetploPrrpurToiloS1nvirc0gao@n,0cdehsenuttLmoihon"iesccteaaadxixilietissnvost..eitilnintongAApg.tcecttdoldeeni1mssetspptseetiatrrssniaatmttsauawit~rrlileefiloon:dSaaaallttiassaampoopporaarobnbnatededcahnmstttaeooddweeiSaalcHclttttuuooaablle In 3M e PdpfEirerloroutpipora veereerorcctthhiiseeeeunm~sLbtisecLatesalsttlttiRius`me~asarncetoteeueespdicsnobbnyysssruetceaottphnhhptiiesssaorsstaafTpCCpoaa8pprrFrrr1ibo~7ziafm-sccop.yhhrortwvvafiavVnlllaatllillduuaeb3betseeMiooonff. TMIchRoee%mapnfafrtooeilldillpooawwwtiiienntsggh miiteshsaesaaunenrreeeidssvttapiitmrmiaoaotptneeedrdtobiwveooCrsrhkrkigf.ol1ro0ascdavras1ff~oodrraatnPPlshhoaanssc.eer ii. f For oA rtinaA ion R and cR he derivatioInSof correlation E~fEraaaggnnmteeinnctcpacctooennsssttaatnnhttessdeffrooirrvattthhieeonHHaan~ossfcchhCSaFadInd?d, LLeeCooF3aappapnprdrooaaCccFhh2 Kow estimation and the ~erivation of correlation ttoo sa~nqcusttiioonns between Kow vs. Sw and Koc vs. rowvanocrhoSuw.rs SSFLFuuuibbnottsscreetttarisltratocett~uooyueerrnnsetta.sscscraooeovnnvurssitatteasaawnnnettnsst,, Fou row ~an-hours 323553--55520000 REIT Property measurement 20%38 300-400 eoSrtraettisattiicoanl aneqaulaytiso~nss 20-25 SFroHperAtyTseasurenents Correlation equations Literature review Property measurements $53%00 5-10 250-350 Statistical ana~ys~s 20-25 Bithod Sleopmint for Koo measurement ~ethod development for Koc measurement Toc measirerncs Koc measurements rs Statistical analysts Total phase 2 Tota! Phase 2 200-300 200-300 fiat] 250-350 2% 20-25 100-3535 1100-1535 22557733..00002255 s0085467 3MA10065487 00000082 3M_MNO0000042 5. riele stuties -20- Caeyya Sp I..N,.m ,E, D_.,I.-Ni",TITIIAALL" Field Studies 1. Backerouns 1. Background TThhhaeeppeppnuusrrppootssoeechooffemiffciiaeelllsdd ssinttuuddtiiheeess reiisssi ttwooorddleedtt:eerrsmiiTnnheee wwrhheaasttults opPophhrfrfaeeettpnddeapoiinnemccnettsccniiooaoontn.nnotfssiir,,rcmnIh,,naaennmdbobduitucthtttaehhlsssreeooyymmwineoeoorttffdiittthsneme,eneenssfurueiFrnneeecaclffooluudvvtteweeersro,,truuulddllnniaapp.ebbrrsooeeTrdrdaiaidhtcetceottotraarerebybyrllmseeiunlets pwWctthhhahheeeueenyrrsyoeeemmmeooaiinvvnnnaeey.tthhaiieenndvIeneettrnhhnesevoveitirhereoenneonrvvfnniifmreerewocononntnrttmsdmse.ecc,nnhhttee,,mmfiiicceaaaalnnlddldssswwthahauececdtctcihuhueeemmsrruullaadoottrereet',,ennroomtthhioonwttwehheeyy cause any adverse effects. IIlpfrnnieaelceletavvdiaa:cllssauuttla.auu'ttddiiyynnggSius1scttheehhxexettsrrtffeeuaamdtmteieeeellsyyaanndadvvcaoesellrfuutfaafeebbrccileetteqssuebbnoouutffttlysrsruauatbrbrosesestltlayaynncccoeessst,,lyato BpbbBteeeerhaecjtS$t0ouuci0osascsttaweiwilifit.doidiefeeedssappnSrreuffecewooaharrddchslletottomouwoidciaavvaelloolsllllsuuuo,wmmwaeeresffuooccrrfhhffeeriemsmeaciaiqscicsuyaayeellnnsstmtR..oloynnfiiittRRetooeloerrdolliieennaarcggssao,:eeisetoaolmncsryaaeyytiinon tttooheaallcllaooswew dodeeftteenccettwiioocnnhemmmaaiyycalnnsoo,tt hhsaauvvfeefioocccicceuunrrtrreefddi..eld release pTTPRarhhrneeea"sseecuunnannttuccsssooenndtpptroorottofleelanlnlctetetiiddoaarllsnnaapmpttrrauuooryrbbeellceeooommffmssp..lffiiiceealUl`tddUnenrresseldttlaauuattddtaeiiededessnnaaaattlluussrrooaall oorr mnintiahenenenatatreceerbhrcpfyyparfrueeesiittcennaat@ddttsuuiissfooottannfrrc,.iitaaotllrhesFFoooorrcrmrhaeeaeaymxxggiaarrcmcriiopapccmllluupeselll,,ttiuucorrfattaatoollexxiiinccdsatacectrdttSaeiiiissvvsticic.ththiiaaecrrssggeessmsaayyffrrmomoamamsskk the effects of the chemicals of interest. pBTFFoooiosrsrnssiiitttbbhhelieeaeeeffnsllsviiuyinnootccrroeeoonccnhhtteeehhnmmeetiirracecealallhhssaar,,sselebtbtaehehseooeuuenngghhkkf,,niooorwwsanyneffppaiirrreeooslldddduuacctssttttiiuuaooddnnyyfeaaniinsnsdd elufiffssioaefemccei~ictlltttelihhsdtteeiisseoeeeesfsn..SvsitiittireesBoBssoyynrmgodettceenoohstseaiiesnlggvuinnaaciillrannuoelggaalstte:eeattshheeettThhhppeefirrosoorrr,ppeeeeyaarrellian--rsswwsttootuurruddlrlaniidtd,eessaff,,waaittfloeoeelmnweeaanndccdaann p3aESerirlficeeflihddeooiciwuctcctstoeeiimvvooopaanfnallssruuiaafsttblboiaiuanosoossnenredoscvoohiofoflennlmllttiyyhhceeaaooilnnsvvseaa.lllleiaiadnbdbioaTiohrtbrtiaylaystte,ooaarrnntydydhienoottbbEhthsseeuneervrnriUu,vvritaaotittnwliiiimiioolettnnlnyysst..aoolff eSLLaTefuaafscfbbfsheooecrrctaatdcstatsocoomarroopyfyfaarnittssdsooiiomnnmmhiisaaellkknaaeecrwreilbsbslueuefotbbtrtsstaettelraasrlnneoscceeseessessttniiacmzobiiasalnnttte.eettsshhteehoeoffffuuEttnttuhuhvererieeroffnwawamtiiteetethhntaaannmmlduducchh less data and hence for less cost. TZTfHahallbbeuullooeerraooloca33hhteeessmniuuiimbmccmumaaata]lririoiznzrreeeessssoiifddrruuoeeeerssssguualltanatsttiscoottafhhfeeneppaDaDseseitctcnaaottfrfuuigirreaelnldppdillcaassnnttFttuuldduiio[(eer11ssi11,:n11oeo22nn))., wTsWsSaahlllsseuuuddcgmgmgdeeeeeiaasstsaahurunnaridrddebedudebetefieftiionnnllnuoeeattnnphohttpefe,,iippoellraadaasgs,nnattnww''ieessllcSllomwvaeaanaasdsssttfeeiiliwwnnnuaaoottrrtteehgohrreeacnhiessttmcoorriiieellcaafattllmvwmuehheoneenrtrrtieene pscCpBerloor'eummedlpplcgoioioenmnrneieicnnnlnhtatuaasrdssryeyewbvqeqeeureutrneaahnnatttaiiipiddtptheealainnittgtteiihii~vvff.eiiefeelddeeu..vSvoaoralmolueBcBuaeheateccftinaalioiuuuoncssonsaeers,ioctchihichteteoemssneisccccaaeanwmnnlneetnorrroteeattyyiooeeonntntllysy hbheaavveeconnncoottludsaeccdccuumstuahllaaattteeh~dighnneeaafrrluotthrheeochppellamannittcalssiittceeo..ncentrations Mmato085:8s 3MA10065488 33M0_0M0N0O000000004433 22557733..00002266 [EI Al a-X 1TYLd -21- see 3 FFLLUIOORRIIDOEE MREEASSUURREENMEENNTTTASSBLEAATT3TTRHEE DDEECCAATTUURR PPLLAANNTT sessures riverine = Jeanie. Measure4 Fluorine mats studs as Inorgan, ic 7200Organic sseluedigueens 22B3 a s730ea sh SsEofoiHfillause((tnSistleuu?dzgee sone 23.7 po 10.9b,0.096 pferaereseols Treated} Decatur Soil 20.0300c 24.4 0440c 8.9 a(untMrMBeaaaajjtoooterrrdTv)uooslltaaantciiisllsee,hCfellsuuyooerrcaocchhhoeensmiileccnaasl vwvaaasss U8 LR 3844-4, 3844-4. IR 3625 ana LR 5625 and bb CrSsFeImTcSirOi2eNsHEt1awesreeis.also identified. aIpdpeanrteinftiedanaLlRyt5i6c2a5l. error (CR Anal. 48937). Apparent analytical error (CRL Anal. #6937). Fish pisces in she pecatur setivent biosoncentrares Fish placed in the Decatur effluent bioconcentrated fob plaicn,tehes, peentar seciuan biormmeniisetat, those !uorochemi=als with low water solubility {38). eins A Residue concentrations n the fish were measured at oa ee Fake matte ar pseaE eee} et 10 ppm for the FOSE amide (CBFI7SO2NHEt) and 7 ppm* BT SLE RE Ce) 1 for LR 3844-4 (CSYlTSO2REtC2H4OB]. Neither LR 2929 Lorn ded pte tl] ee nor L~ 5625 was detected. EAI 80021 was detected but or Ease not quantified. hie greater bionccumiation of lov water sobs This greater b~oaccumulatlon of low water soluble ee LIEed Benen fluorochemicals agrees with SAR relationships between fret HE Siganic crenteats 1.537 bioaccumulation and water solubility or octanol-water partition coefficient derived for nonfluorinated organic chemicals (24,39). S *sFro9re ppE eerrssppeucrR ttiivvee,, S FFiDnA paililoowwss 303 PCB sonsenseastens concentrations vp up v6 to 2 pp ppm fn in edible portions of fish. Suntcosss 3MA10065489 Sans 3M_MN00000044 22557733..00002277 a : -. -223. riels stusy ax pecatur pian "INTIAL '2. Field Stud~ at Decatur Plant 3 fiels study is recomended to sessure alstrisution. A field study is recommended to measure distribution, A re biological uptake, and effects of fluorochemicals freteR Se lg near the Decatur plant. In this study, we want to SetienineenT} IE Hantocntniiats Sve tons. tied og determine: l) if fluorochemicals are long lived as Sneath; 3) Hf dietioneninn ven, nn Le us predicted; 2) if they concentrate near the point of ea alfutes! oneamoss Sra sheiserbents 3 entry or are diluted throughout the environment; 3) ris a oe aatiepent AE the if they concentrate in one compartment of the a LL EE al setians or environment such as air, water, soil, sediment or RTI ie ae any seca totes Sh. biota; 4) if they cause any ecological effects. Fluososhenicals have been produced at the Decatus Fluorochemicals have been produced at the Decatur Te TE Toate Sle her, sion Love plant for about thirty years. Since then, they have Be area tot elcbasent hisswt. Lande Ling of been :entering the environment through landfilllng of EC hytore er GL tars and other by-products, through water discharges, a Seri Tr tea cin both before and after the installation of s modern er Teme che ty hasan, vena wastewater treatment facility, through vapor HI En priate. ahs discharges from ma~ufacturlng ~rccesses and er ne theta; theousn wastewster aeration basins, and more recently through Beis esreration of wastewater shotos' the field Incorporation of wastewater sludge ret Een containing fluorochemicals. Analytica: capabiiities will be tested and evaluated Analytical capabilities will be tested and evaluated BRS SRE Salen prior to study initiation. While there is concern fr EE RH about all fluorochemlcals produced at Decatur, we EP eesiristoostomn arid: plan to monitor only three (perfluorooctanoic acid, Be er oat ae EA SSH Spas rie perfluorooctyl sulfonate, and DR 3844-4). Specific Done aves fi andr ot mats atbe Sect analyses, however, will only be made after first SHIRL TS Men determining the need by looking at the levels of Se hte EA Rahul Siteinins total organic fluorine. This preliminary screening lar ee LE for total organic fluorine will eliminate an fritter unnecessarily large number of costly specific fluoroSonesta eee poner: SES IEICE Sent chemical analyses, We can obtain estimations on how ee Hhemieat hia re ont inetas Sheniaats moon these chemicals and other fluorinated chemicals move Lea Ba avdronmene by Tonting St Suet srsenic and act in the environment by looking at ~ust organic Hn fluorine. 4 comparison of the difference between the total A comparison of the difference between the total TE Ee ME The Sovcsotgation organic fluorine concentration and the concentration Te ent trea ent eal3 some of the three specific monitored chemicals would Thaleee oheehit ster Fhsocinetes chenieats aay bo indicate whether other fluorinated chemicals may be eros easteetrints. 28, Boe important as environmental contaminants, and thus TEE) Resta atne be Thenaifios: Stoer whether they should also be identified. Other ani 12 Mattie antiites 1n fluorochemicals found in significant quantities in SEnrEinL LAr Decatur soil, sludge, biota, wastewater, an@ rn RT pT lrae~ecseeoiivbaienTg~aenwneatItieEfriieebhdy matenntdehoqqduusaanntsiiuctcahactiiaovseellcsyapSideletlteaerrrnymiinnGeeLs~C miTannyetre the study. me 3MA10065490 auamoscones 3M_MNO0000045 22557733..00002288 Ie analytical cach=niaues selected aust have adequTatIeAL The analytical techniques selected must have adequate eee Se ornchenisats To enters sostiate specificity for 3~ fluorochemicals to ensure accurate Es ofdes vo s00Ls Folge Fiseme: identification in order to avoid false alarms. EE J Analytical work, done to determine if Tennessee River fic mL PAR LL fish bioconcentrated 3K fluorochemicalS, has clearly Heim pete, ly Lor Toentetie hoo, Hest illustrated the potential for incorrect resuIts with MASE LE CL II Te nonspecific analytical techniques(40,41). In this Tone EAISToAL GE) elas ruth siecteen Shpture study, preliminary GLC analysis with electron capture Em Sa 1 Hee detection separated three peaks from fish extracts fie ety that moved idantleall7 to those of three 3M fluoroLI ATE Co, heenJn Shere chemical controls (40~. Rad analysis stoppe~ here, EAs Sons Shpestes coat ab ietochontEete mae it would have appeared that 3~ f~uorochemicals were Sloot Ear 2 unre bioconcentrating into fish from ambient ras concent~atlons. ~owever, confirmational analytical PErere ee work ~sing microwave sustained helium plasma cenaaees ts the hooks Shan Ba" FERy inane detection showed that the ~eak~ from the fish tissue te ep Sad extracts were not due to fluo~ochemicals (41). PO ------ Before sampling, conceptual modeling will be fr opis gyloei ogo JI conducted in an attempt to predict the field study eres? a TE Te Lele SY, findings. These predictions will be baaed on old and I gt SE new laboratory data, available ~ischarge reor~s, and i Tr ey maps of the site. When possible, wi~ely use~ tent Sodeid mach a che Pha 5 PARS yscen environmental models such as the EPA's EXAMS System tire ge th yok will also be applied. This exercise will help tO an er A ensure a meaningful interpreation of the field study Shine San results and will immediately draw attention to a re RT uns tng unexpected results. It will also help in evaluating par SEAR Uy ty the applicability of existing models, which are based ne Or, he he mostly on hydrocarbon data, in predicting the TR rEet enieadl environmental behavior of fluorochemicals. ne fotlowing is a List of propsses sampling sites The following is a list of proposed sampling sites fugit gngba ovsgl chop and procedures. These procedures and sites may be es ee ties tote Tato en a provereish of s~juste4 as other information on the properties of Fp Eh pr ST the chemicals and nature of the sampling sites become Th oF smn ae LAL SECT available. At the time of sampling, complete ~etails SE hs Tee I RI of the sampling sites, including pictures, will be Les recorded. a2 sues a) Sludge 2 seciee of vxah state saspies wild be taken 19 A series of grab sludge samples will be taken to Ee Le LES Hasse compare with other samples previously taken. Sludge CoE htee ann EL ae should be sampled when it is being pumped from ee ar LL emsFedCr 1 oe storage to be applied to fields. The results will be ee ER CE SE used to estimate quantities and variability of Be atte choo fluorochemicals entering the soil environment through Asmar Ante Se sludge incorporation. (7 samples, 96 hrs.) -- 3MA10065491 pr 3M_MN00000046 22557733..00002299 -24- b) Feluent SHAD bEfiffofllluuoeegnnitctalwwilitllrleabbeetmeccnootlllleesccyttseetddemasbttef~tohhreeeoouum~tifx1lioonwwg owofifthtthhee cwcbiooilooolllloiinngagglicsw Voaalatbteeterrre..caatlmCC coueonlnncatcetenestndyrstratbaetam tisiooenndbsseofoneenrnetrteeerm lriianintxggiinvgetthheew flitorrhewesseerrarvtveoosiirr w 2pannrddielsl etthnhaetelsoaaisnsssbeucurompocptlatiiiloconnung lawtthtahetaadettr.nbnooaseOfdnl1euuooon5rr-oolcrceihhetelasemirtiiccvasaelalssmpfllaaoertweewiralltesbe vptEaaarkerkeisenanetniddtouunrirniinniggncoeetoaahlcecinhhgefooffwflaufftoeoenuurtrr. ddcOihiffanffereearrc5eet-nneltrtitieswwtereeiekcsksssamsc5po0alen tthw bhaea~till thebe the etevuvvaoaarliluauwaaattistoeetnded.. t~rn`S eSatiihntnemggelleneetfccflosounynetstrntrooetlmlssschw vnaiorltilallctaatrelelssraoiotsitnbbicgeestftaaclkakueneonnrobe-ffrroomn cecthsh~etoemimimwcaiacatsalitlseos.n. troefT?ahh~eetmheerrnee~qssuuualslntytstssitetoomiffesstthhneeooftaantnfrllleyyuassoirtisisoncgw whielisfllliluco3gailrivovsee- aann eeetnnhstotteiesm rreSiannftggiroonmtthheesoefdllaiathkmkeeee.n. tquT~aahhnneedtibvvtiiaaeollustueae.ssofw w(6iflliullsloarmbboepeclheccesoo,m m mppta8ca4rareelsddhrsw w.ii)tthh those from sediment and b~ota. (6 samples, 84 hrs.) ssooinl SSionoicilolrpffrororomantetthdheewiffilielellddbsse wwchohelerlreeectsslelududdggieen hhaaacsscorbbedeeaennnce with aaEinclccccuoeeoprrpptiteoendderamtmaeneeddtt,hhoowddissfill t((4hb42i2e)s) caaoinnslddlefcaaotnuneanadldlyyzziineenddahiffcogochrorrdqttaouonattacanletliotowririggethasan,niicc AAfffolppolurpperorr1oodr`thitsxxnheiieemminaatthttahreeernelelidecfyy,fetfitlrfeeluennuonotrthrssooaaicscmmlhhppoelelcism eemassitiiccfooavwaunliilssnsll,lldssbpbpinSeeeeeccmichcipfooifgilillehiellddneegccqttaaudeebbaeddoopvnvtefeft.hirr.tooiewmmisl,ttlhhee bbfeeieblbdeesttwweeieennndittfhhfeeersseuunrrtffaaccleeocaaatnn~ddon11s22.".. Sampling ~epth w~ll aIInnnpaalddeddsiittiifoornnomttoothetthhedessieetchsseaasmmppltleehsas,t, aacpopplprlroeocxxtiim maratutenelolyyffsswiixaxtessoroiill sfsfralrooumnmdpgleettshheeapfpffrliioiemeclldadtthiwweiiollndllitarcbheheese.sttaakkteehnnat aattcopPlooliiencntttss roouuunttossfifiddeewatttheheer sludge application area. TsTwawoone ccoosnnotitrlroolltssypwweiillallt bbleeeastttaakkee1nn0 fmfrrioolmmesaarllooorccaatttiihoeonn wwiitthh tthhee mmSsaaaanmrneupuflfaiascncotgtlulurrsiiitnntyggepseffwaaaictcliilllliiettabyysa..tseiTtT0hheemaifeeltxxeeaasrccttrfreolvlmoiocecawattthieioofonnssthoeoff stlthhueedge psiiaanntmcctpooelrrrippnnoosgrraatotsefeiterTtsahaetteewssiflileiilnndbstet.hheesetffiieeallfddtsseraannrddevittheheew orrfuunnootffhffe sludge patterns of the fields. TTbehhee ursreeessduulltttossesfftrrioonnmatttehheehoaawnnaamlluyycssihissofooff thttehheessaeeppslsaiamemppdlleess wwiillll mbffuellcuuhouorsroeoocfdchheettmsohliecceaasflltliusmsotatrataiyyenssatheoiindnw msttulhheceuhdgsseoooiifllistaahttweasatthhhpeeepdlisse~ifdttreeonaanntddhehhooww msffuiaicenehllpddl,,iosf,ppoots2sh5ses2iibbflhllyyuso.rtt)ioonatththeeedaaddsjjlaauccdeegnnett isrreeswseearrsvvhooeiidrr..fro((m1188 the samples, 252 hrs.) d2]) FFiieelldd Vveeggeettaattiioonn SSfiirxxonccrrFooippe1sssaammpprlleeecsseivwwiiillnllg bsbeeludccgooelllleaeccnttdee~dtwoaattfhrhaoasrrvveecssottntrttoiilmmee from fields receiving sludge and two fro~ control fields. Wk10085402 3MA10065492 3WM_N_MN0N2000000000044T7 22557733..00003300 SThheepsseeassnaammipplleeessnww.illlll"aTffshiierrnssttEbbeehsaamnraaellyysza eetdde K~foonrr ttToootttaaaJlls, TA cre SEoc3S8rrE4ogUEU4paT-sna4iTA;,cwiANlaaflnlndu?eoBbsraeeinarTTeahonn.ttaielayfFyzTteoeeheersdedaeniinnfecqgooi'rfrssttEotLuuRRhddeyyret5eh6a2suus5saa;,iritneneggtEEAaAhIIiittgnhhhegeS8O~cQ0lcS2rSeir1vLooo,espalswaia,wiiniidlellltlhiLenR BfbbfFeeelaluuetosit0orenhoioedctdceaieartatrabtseoeeotraednnmnc.siisynnee4ffeTriohott1smehheetbptuhhuukeeprastpearocctksrreeeoopFp.FEkoifinonehfTetththeinieeccaasddfneeetsoectafd1.ai5illnttssg1hhseeoosfftudttyhheewill aaFfEppeEpperrdTooipnthrgteiialstteteeur.ldo"yf((nfw8eilsslasamenpbbpleeleiesest,se)t 1i0ci8kf Arahat or when hrs not iditnncciilsvuadiinngg o Feito possible feeding studies) OaCefEnn)/eleeutioPoTrariieglamaoc!tponhoohrseuretmttnaaiifnncortt~naIinspZpoposlsiJnassntnii~eesbo.ileepttahheern~aosddeeeeenancvootoiiffurcrooinreenmmnngeettnrnetytyproooiffrcsesttttshhhheeeresoouuogghfn aatier S vseSHyopmEsaliUttasTeetsT Ems;i..:loJnzsa"aCrC thehfeiremouomlnmslcaeapBdltlluul?ssteynteCtneormtibtaetaerniheriurenenfartg~atiacioitotSinhnuhoereeiooenfSefdgon.uvthiiphneorerenoooancwaamearnesstttntshet.eeesstttHiohrrirrreeroasoutattgmioohdeanntt RcuttShsnhheueeaearecelanaiflittoyreorasealStrooieccccoaaaanllrrulirzsyyiilu."eseaddlluWyoaSMhhfEieEfeaennfi-oohtrryhttheheGtretrrhrheeeede'ayy~tl1ies5upbsrtrteeesscdcuui"tccCphph~liinotstfsasoaaettllsesilttoohvuoeotottuu.,stta,,itrhttehheeand SEE Fans concentration is SEL EL RE usually greatest closest toithee , TSTashahnouudmusspr,,lcaaitenwwgeeaiEnnrpdpvcrareroocefsptpaaiooosisrsllnesesnggssvoaoafEdmumfiiplpstdlltwaiiainnbnntdeghcgeesstsdtehh~teesffr~rosuasopomonn:iiclletthh.TecefcolrleoppooslmaseafernitttrthS..soeot sttMwThhoeewuooroocpplell.aanntt oSSsfEtooaoehlmlEeTpleoralonciwtnuaEgpTtpdwnhuieevinTendicpGd.otrrnoeargdssoeFFmonoeiutuawncrronhauenlnssdtveooies!docbeotowcsovoonrsmrrweveetiaitnn.dsguspa.ai.mitnrpxrtElaaeiedTjrssheveeacclwttosooofuurtillyrsoddfstaannbblewedeooonutt,lhhdee Sfc2t0iaoo0kklo~eelr,nneLct"Ss4eiSoe0od0vui~een,arzaaallloaarnnngmddmiille$8enea0s0esc0.0a~h..firvrBoeomT"cntPwtuootsthrhhleecceooalptnpnl~ttaarWrinnoonittll.ti."erssvspaoaTmzThtlhppese!i.eebessolofoviwccaiaa1itlkt0lilei0osMo,nnbbeetrii~son yEt{ehhtooRsseetoTpsoboeilnnHttdsseRtewwrhhCmeeirrneeehdssa.aammppFllSiiiavnnmeggp?levv(see1c8ctwtiooFlrralssmotniIeonnnttt.eebrress1ee44cctttabkrevwanaalss:ttfeerom dispsoessatlmenst~tes or the r~ver (i0 samples, 144 hrs). pPfPFf)ririeeeuuvvoSoitirerooodaueucicssmhheeenmnssTtitiotucucddaaHiItieenssssbbibihhinnaandvvdaee ctsfsooohhoossrwooTnn~ialtunctthahaiaannetdtd ssStteeehhdvvuufeesserreaaswnllootuualool!fdfs btbteheh"Teeor wate S~EerEHeerxaeapETsecRoceGhRntloeowBdntthRmaheIut"etCcerroeEh'eianlfHeistsl1suoouisoaaicrtbeoohinmniceneethhdeaedsis~eatmiconttiocieocaraeleqTalonucootdaeaokokteeiivsscneaatrtybabsiiaescnndqsqedeiesu.:rmpeaeictncititciCccesyhrn..deesdmneeiitddtccnicFim aaenoliaresnnantrttehit0os wvdufGtaaes~httcuaaEeertacrraltTsstlibecyicneeneanndfotttoueeewutnrrnoiddihsanstieinnSoldllaiaikmhHtketeihoeuengnonothercressereappndoecodicnrmuoodaeenna..nyrccteaenntTTvttrihherorneernaayttwiicacSoooothrnnnneeacsscrpeeiendnwwnttlthhteyrreern,aarrydttepeioiatoionesonndnfitft.liauor(eeu1nn)tt FSdFeHo~eforfcEElrauetheeahSnnisEtstes cEreRewoenEaiattSmtszrohoyynnM,:dpbTooieilswwRnneetetanpphcrraaeeonnopddpoooalsswaaieettacyhtcttahohofeser'ossonmammemiirpdgFtpldlahseolelweesSse.eseandndntiiddrmiSyeiemmnnropoctueouetithnahatttt.ooh(fettlhn~ee EfthlIeo0wL5coGovREfe htehieendtoeSfeefwklhlTiuoecemnhnntsotthaaeftErtedesd~:iTseceThnnattreegrtFeiionnhggfolnotcwhhesen..E~cReeeSssieenVrrcavvee~otiios~tehsesc?aann vary, a~ditional sampling will follow three vectors: akr006s483 3MA10065493 anonoons 3M_MN00000048 22557733..00003311 1EE. | a. AD -26- "' Snns Shes a Sun hedAnsHoge0, one up the shore line: one down the shoce line,, and one perpendicular to the shore line. Sampling depth will be determined on-slte an~ will depend on the Re bottom topography along each vector. Control samples aD will also be taken from points on the river well DD Dra Eh Di cy Sie above and below the plant site. Only the top i-2 centimeters of sediment would be sampled. The EE Let Bi Tr 1 sampling metho~ has not been ~etermined yet, but it could be either done by diving and scraping the top SS I-2 centimers or by using a vsnbean sampler with a Se nie i NY, removable top to obtain the top 1-2 centimeters. (9 samples, 132 hrs.) : There will be two types of biotic sampling. First, to estimate possible effects and second, to ~etermine 1 Eft Forel thre Teg if biota accumulate fluorochem~cals. The sampling RE Se points will be the same as for the sediment ssmples for the same reason and so that the concentrations i, Br he sam Tease 3,hes the Someta the sediment can be directly compared with the Dr SR Sn concentration in the biota. If there is an effect on will likely ~ecrease with increasing concentration of the chemical causing the effect. The clam, Corbicula, will be sampled in order to determine the Seeeieniwnii Se Samplived oloe LoSEvimaine.S concent~atlon of fluorochemicals in biota.(43) samples, 204 hrs.) vr ver Gotomn h) Water Column The concentration of fluorochemicals in the water column will be measure~ at each of the sites where the biota an~ sediment are sample~ in order to directly compare the concentration of fluorochemicals Ne in the water versus the sediment and the biota. The parts of the water column that will be sampled will Br EA se depend on the mixing pattern of the water, the flow of the effluent, and topography of sampling sites. One possibility is to sample water close to the bottom, at the middle of the water column, a~ close tO the surface. (12 samples, 168 hrs.) Priority This field work is needed for three reasons: I) very little data now exists on the actual environmental Ease concentration and impact of fluorochemicals; 2) the study will assist in clarifying those physical, rn ey chemical, an~ biochemical properties of fluorochemicals that are m~st important i~ Sree SE sineSit determining ~beir environmental fate; 3) it will provide the n~cessary ~ata for validation or correction of our present estimated environmenta~ concentrations from our modeling studies. -- 3MA10065494 ois 3M_MN00000049 2573.0032 i. TiAl -27Ie pricy objective of th tisie seut, Seuss, is The primary objective o the field study, however, is to determine if unanticipated or unreasonably high floorochem~cal concentration exists in any site near the Decatur manufacturing plant and to extend such Setter icin sie 2 ne information to predictions at other manufacturlng and use sites. i sats of thi study see sive he foioving The phases of this study are given the following ee priority: Trae 1 (eons paipeica capiiisies) - Phase 1 (confirm analytical capabilities) - Priority I - 150 hours fry Phase 2 [modeling to predict findings) Priority I - 20 hours PS eleie TEESE wna core smarter = Phase 3 (field Samples and sample analysis) - Priority III- 1200 hours C. Incineration I. Background S SETieIO Incomplete combustion of fluorochemicals can lead to the formation of acutely toxic by-products such as carbonyl fluori~e and perfluoroisobutylene in addition to the HF normally formed. Incineration stuOies conducted by EE&PC at a pilot scale incineration facility looked for p~ssible toxic by-products (sUch as CF20, OF2, perfluoroolefins or Beran athe Cop aBerney NF3) from cc 788-19 (100 ml) combustion (w~tb 5 gallons #2 fuel oil) at 2185F. None of these components were detecte~ at 1 and 5 ppm in Sabon dhe Le condensable and volatile components, respectively. ~owever, literature sources describing other Be eee reeSey OE me fluorochemical combustion studies have observed some of these toxic components (44). . spproms ng oecision seins 2. Approval and Decision Points 3 son burn ot hsroetenients x she Daur A test burn of fluorochemicals at the Decatur incinerator is recommended. The Decatur incinerator has been selected for this study because it is more femelle feito, et TE likely to allow the formatlcn of incomplete ccmbust~o~ products than the more sophisticated ChemoZite incinerator. Thus, if the Decatur incinerator ~oes not produce significant leve~s of toxic by-products, we would assume that the similar Cordova or more modern Chemollte incinerators are at least as effective in destroyin@ fluorochemicals wlthout producing toxic by-products. f-- 3MA10065495 ap 3M_MN00000050 2573.0033 [---------- -28- FA JLATIINTIAL SSSaSaunnamagamplolplytylezsessestedeadooffffosorrttthaheHAceFrkm~aagaanutntssdeerriTaTiaoonalttaleal]lyttotoiOOcrrbbaegeglaanniiniipncccacirinaFFnesilerevuraocoatrreteiirednnsdee;:vw iinlcilllludbbeee or, CSCEFF332a00ni((cccaaCrrobbroobnneyynll ff(ll1uu0oo0r)ri,iddeet))o;,talppeerroftrllsuuaoonrriosclissfoaibbvuuottryyilldeee,nnee,,andttoottcaaoll organic carbon (T~C), total organic 1uoride, and CO. AASSsnntrtaaaaallbblyiyiutltlniliittctceyayad,l.lpaccarnnaaodgppcaappbbrriiSelleosiistetetirihreeevvssaatttiieaaoonnnnntdd.ssrfaaeemmTqgappuolliieeSrteeohhmnnaaeennnnddottllFssiinnwwtggiih,,liellse bbee hepRCPoaovoonnsnsaddscslilieiuiiblbainllltngebeegtdiabdbopyliynr-fe-fpBipiriorocoerorududluiucttctcholtitaescsntsegheeaasrcaaerertoeetqsgotauua.nilnPttttoiee~rccsAilsiFrppoeeaanaasttsccoeetmtddeiiovvfeeaoa,,nftndhistssacahcmomeoPpupusrlllleoeed~poccsaaiuulss.ee cancellation or changes ~o por~ions of this proposal. 3. priority TGTiTEhhfn"eeceetashnsseettouunDdDeaeyhybcciaaiietstsuurrsaapacci(uoonnnnncctffiisiinnrreemmrroafaaattttcooooorrrrnyycddeoottneeeetssssrttaootkrppillodadanonomseneesesddofntotot~chtoas~eteeemmerliilalttouuusss Gdueensgrrreaaaddsaaottniiaoobnnlepprraoomddouuuccn~ttsss.. or concentrations of hazardous A PPrrtioorriittyy IIIIII is Js aassssiiggnneedd ttoo this this pprrooppoossaall.. 22557733..00003344 WMAI0065498 3MA100654.96 S_UNOX0SS 3M_MN00000051 I === "n= NTA IV. ENVIRONMENTAL PROPERTIES OF-29F-LUOROCHENICAL CLASSES IV. ATilcEhlNcaisaVmslsIsRaaessOrsneeNccMdoottErfiiNosoTnnA3DhMLeecrsePeEfvviRlSiivOueeaPoawnrErtssaRoccTehhIooreeuEunmcrS.ilccOppasrFrtleesnsssF::ueeLnnUettOAARs:.KkOnnCaooHwwIEIcllnMneeeeIiddrrCgttagAbeeLneLLiiooCtfsqfLuuAeiiSttodShPhsssEeeh:;SofftBBooi,ellnllaootwwLLeiioaonnwsggwoMsmW S EER E ReR da1 cotatoiie.tines, Acids and Their Salts; C. Surfactants; ~Icoho/s~ F. Acrylates~ G. Urethanes; .D. H. FEOBAEEY ane PhosphateS; E. FLUORELe and TTcKiThhenoaeetltcoo-tFsaaeaecicc.ttPt"aiioBoaolanTnytcmhkkeeogorrnnrosBou;aueencnaxakdccao""hhnrdossfueelnlIc.csuut.tooiirrooosCon~ncecthchaetaeelmnix,ndioiydcncssatsaasll.Ro"ucRcetlelclacsoisoamnsmsemmeieLnussnddreffsduuprcrSTtteeehhssseeettrrinintnddggii"vviiddeeds isutRCnhennadecidteeiEeftrollesEnstutf.aaoaenrrncadootlicTcannhhhggeee~rTiioo~hfcfaaealcl.ktthgh`eerRlc.oleoueaecssnnnosdvvms'iimrresoonppenndhhcmmeyyteesdsiininoccnttTasaaeellllsltloiyppyunrrtgoosls:ppiiieenggrrennsctiieiiffcoeeiitussccir:,aoannnpttdrdeepessragaecorssnepapptsodeessaccbebttisissllilooetffyy., 3iaoaSund0Itddt0piTuteUptLif.ofCuennncaTtliEEscsa.chswoohtr;trkhTstkehte.euuaaddnnmyadyi"sRggbeiLiisaxcvvroeeggsmrsiimvveieedn~nnnededeccidlc8iaasstpiBiTer0HoeinisnotoboripEptnioLohgtiti'"ynyntttsshfsreaeacttaatiinnniddnnaoggdnaeeoxOxFfppparneedoccI1,,tpeeoetdssh1Ie1e:I.,sstoeersosodttrfer Ii{nIITwheiinchhwhittchheeh pptrrhooeppoonssueemddbersssttvudsiilneedssicassthheoouslibddotbhbeetSdhooenneen..eed end the order pTTpErhhreoeeoptfclippeTlrrseeooarspnpcooaossonncee'iddviiepnphhdheoyiylfvssviiiidcchuuaaeeallsnle.pprfrEololiuppbmoeeoprrrroototrcciiehaheeneesstmniinmccee(aaaallissussuuocrrewewoshmhcaieihnccnethhtnssicaaarvrweleiillllclabbsrrsooeassdd:eenn hTrThaeietpaserseeasSdneaadntttaea2t:wiw3iivllellGoaftbbaee tVbuhaosecsesse~e bbfiooomrttphhoSrAtttaRoontmmdooedtvfeeelllluooptrtmhoheecenilhtrre.mleecnnavvliirroocnnlmmaeessnnettsaa.ll DpDPEfoeleaosgostssertriihaaobaddallsaaneeitdtciiaoocealnnrnsssyvioiafcrssoottdnnpuuamhcddteoeiiantneeotstsbtaaahlwwlseiienlldSlileefcgogardrdrleaea)tdtdSeeeAarrtRatrmmiieoiio.dnnnneeevipmemewelwphchcooiiphhrccmatahheann,,nniittss.mniLsfsfinaa((nntccyyhhh,,eeemmooiiffccaalltt,,hhee eebnn~vvciiczhroeommnimmcaeannlttaallor ffpaahtteeotooocffhettmhhieecaFflll)uuooraroroecnheeinmmiipccosarlltancctllaassissneesst..he EEFfflffueesccrttossthattsaeisscttaiilnnsgg wvtiihllal)t dcdeeottleesrrnmiisnndeeverttshheeelyccoonnscciefenenctttrraattsiicooonnlosooiffcel fluorochemlcals that coul~ adversely affect ecological ToTshhyoeesesstteeeimnstt.ghhrreeaeena ttyy"Hppieeesslaooffsatddaaa,ttaa..wilwwlhheennpeuulsrsee~d ainngonccgoommbbniisnniaacttaiitooinnonvwiittohhf the mlEToiiidkoeeerllloii{cnhnhgo%eoonddatncdo"n0ftfaaiCdedlvlvadeesrcssdeeeast.aee,nnvviiwrrioolnm!mseiynnitteaallld eeaffffgeeoccottdss ifFnrrdooimncatttihhoeensreeof3IMKthe AfluoIrnoecrhtemlLciagluiccelasses. A. I1.nertmcLkiaqruoiudnss I. B0ackueraoyusnicdal properties a) CScPoohmnyTmsseeiIrccaceTlti2aallRProCcRphheeeTCrmmntiiicceaassllussmmaDpriiivvsiiessstioonnheTTeecpchhhnynisicicacalallbbrroocchhuurzee TYFBpphar-rreveoIosafpTpeeeePrrBsttd-duaiiIafteet(iasss2i1c.iooif3fofnn)ndaJtiFfFRclclvauauototoslereruiaimntnmtteieahhrlraarttttiitzyeEaGElsl1ll1etecotctFFhtreLcErroUOoenpOCsnihRRtscyIIssN.NiEELLcRiRisaTqYghluueiinl1ddiisetqg..uouiidoss heSSaveevenenietsnusaauetlfnllfyyi.cieeevvnaatppoorrvaaottleeatiaalnn~istydSiisstppoeerreseneeabliiennttoothettmhhee to atmosphere. aMAT0085497 3MA10065497 a oo000s2 3M_MNOOO00052 22557733..00003355 Calculations "-3300-based on < ~i .: ul models deveioped by rIoNmTaII A\LL CC CtEShoheaueepnlpioctvFiFutteLLtldVaUODt((ib4RR4oyI35Zn3NN)sdERiRssshTTmbosoawousl1ileiqvdgetuhiurinaioadgtndts,s, mionaoaonrnrdeeccseeealisnnnoiiontndtweattvllhitheikeeekloerepllaayeoyttm dfmottoobobssyyp.phbbheeeerree., S3SaraeFnEd3myosocorCcvhrbaeaebisdssinnete?ggb, yibbnttoeeeodcrcistaaaausunnssdodfeellvsusiooeoentfrfgttotlchtliihhinnenegelgnieirracwwahhiiiniittighsghhhwprpavvaeatormeorltortaliviactceouiudtrlilllaiabiftttytryeyeo,s,ns..aatnnhyeyIn SoaavttfmemnoothtssetppsheheelerlreeyinbbeFyyeretvtthah~eeplsusoeeoraropptcrerohocceteeomsssistceehasselsavwtiremlilmollsopiviiheikedkereellf.yryom the eventually ~eevaporate to the atmosphere. FPSpSochhomreyyesseiieccxuuaaannlmlaapnnlpspserwwr,eooerppreeeehddrrottwiiqqeeusussetesrstoootinffioognnlttssyhheeddoooiinneteeehxrxrteitiysstftfalldccuvsooooorntnrococbcceehhrreetnn~noiinJingccsgaaollittsshlh:.ee} SaS2SFn07ooo~iarlilv1eded"nexeTstattoosmearr.prcbplmatteiiiai,nnoroeenenhdodlLiaffwaittkaaesttlhtheyersayyoil,,nlito~oowlwllsmis~ikokeevdvueoasssooft~tmmoohreeeoynppcrcrheheasldldpdoiiosilcrorcltriitbnnaapmattaonteebaboddiilllsiiaotntidyly? fdsSS~iooaolsuulmerfpvoccoeseenstanstao]..sl,evssaiiT"aTltthrhueeeeeasstEElenaaninnvvkdsiiterhrlcioocysonnonmmntteeptonnaoattmsmmaaiiaollnnivaabettiLLeelaafibbrtgogooyrmrrroaoaustutsnonoptdrrdiawlyywrlaatstseheharoronduullddlanbb~ee GdaF((eebSSLvvlAAOReReeO))llRooItppNoCcmmEaaeeReppnnTvaattbSapiltluLooiiafiftttqiieusseeittssdrrt..suuh,iccsttTTuudhhrripeeeesocsuslaalslococsbwtwteiiidvlttviiooittxxbtyiyieylccoiiarrwttfee,yytlleaarorottffaiikooennssshhiitpphssis pSopcFhoonoLettpmUneelpOinnalRcttteIaiiatNlaslEesll'yRl"TyppinrriioonLnbgbninlrioqoeocuecmuiuundonosudunn,ssuoo,,snntccdereittriishhtteeciiu1ccs5ppaasrrll5eee,,dssseeebnnbbnucucectteeliotwooee,iffvvveeennmmmaaanknaii-e-nffsmdmaaddhteeihgihs bcprhroeormfiiilcleaelsssuubbijjneeccgttr..oundwater is a sensitive and high 5b)) DDeeggrraasdaattiioonD aEFFrnleleevcusoloirrpisoorttcyciihihnneleggncmaiiddlcceeaaggllrrcaaoddniiaadnntiteeitrriiottoonnnllsiiuu:gqnnuuddiieeddrIrssnbboosaattrrahheeditsvvejeexxorritnyytr:eenmsssetttahabebccllshheeeee,,mmiiccaall aTl1ini0gdg7uu8fi0pad0htsy'sanihsdchoaowlowthcnneooorndssibuutissioccodeaneppsgte.riiabndiialiItniiittoyyanddttiootteisbbotiineoo.,ddeeggtrrhaaessdeaattiioonn in BOD and other biodegradation tests. ThTTiyhhnnpee"oritttehrhheee"sssstaitStasma.mbbooiirsliippiehhtaeyysrrueebsssuutggfgagoforeenrssttvtvisesesrrtyyattdhhaalltotobnnyggttahhneettayyiilzmeeywwsstii..illclls)TEpphneeiirrsxssiisat PTTihfehhyinreepnafyydoilitninhEfgcgoeosurssunoingasdoo.iffsitteDDshhtiiaahettesyttulpzspbceesyrrtaacfnfnaidl~lnouuthococierroaoxo-otwsmwemonsoderetrtkkhhbeeyyhyrrlolssevcaeyyncca((llrl46ooey6:hhmt,4eeai47xicx7.anaa,4neln48ed8e)).aainnnd~ the mSpaStaetihhjrmeoeofoiserlrspiupntohtteyreoororctdeaeaoiylfmnnveewetoatohatrhrer'ylsdldetticwhhyiaectcdweeloccooohppnbnerrcecxooereaddnfnnuutlteccrruttaaoiittrhooiiaonnovoc.:ennhenree`iTexxThcmppheaaeeeliccssngtecereeddedvaaettriffenrroommthe lmRrhE~aeeadijllggoeteears',saifeet1ddyuaaonndrdoStofooceehiitttecghhhneehheitcsceyaayattlmmpptooeewsrsro1capcpeehhpnneeesttrrrt,,eefillouoiifonrnrihpopttocohhsehsetseshimie11o~b99clla44ayy0t0l's'ssosasslipllawa,h,tteerceSOooeaaff.xk this fluorochemical is still in the atmosphere. PaSDDrumrUoeieid~nueettcssootssatthbhhooaeevrveeettrrana2dno8nast0sptapnraneenmrxnepcneyT(ccH4yt.9e,5doo5f6f0,,f5EopT1eL,drpE5eef2rglH)trul,aoydroeotOrphoReapienrcaTFafLtItfUhGieiOiRnRnsIgENEEaaRnnTedT eCpcEtoroinrnonCocEdtrpeauaoosicits:ntpnpishihneenvgrrgaaeevreeFFlooLLefrVUnnOoGctRRlltIIoohNvNweeEeExrrR0Rp7TeTcssttsbtperrhrrdaoeaodtotdvoruotecpssocttppssihhd,,eoeernrge,erUw.:ahhiOiRcecahhyNNiiithtnhraravovoteesgheeenntt--nhee longest wavelength []V absorption, may kr0065408 3MA10065498 aW_WN0D0000S3 3M_MNO0000053 22557733..00003366 a TAL photodegrade in the m~d-st~atosphere, but other Bast inn slope FLUORINERT chemicals will probably only photodegrade in the upper stratosphere and above. Unlike other organic materiels, degradation of te menest Sa inert liquids through reaction with OR radical is alan unlikely to provide a significant sink for smiley psp,sipleicn: dle, perfluorocarbons ~53). Reactions with O(ID) hH(aawvvheeichsSoommoeeccussriisggnnipitfriiiccmaaannrcciee'ly ((5i5n33)).the a stratosphere) may The lifetime of these products is probably Tnete pm, determined by the extremely long time required shite ethene ni, for molecules to diffuse into the upper regions qf the atmosphere where photolysis, SottndSRnS HE In wis photooxidation or significant reaction with pmsl of sion) th sing/et oxygen can occur (54). Estimated atmospheric lifetimes of perfluorocarbons due to these reactions are on the order of hundreds of years (53). retainer sizer dining on entreEin Preliminary literature findings on chlorofluoro- methanes and ethanes suggest that FLUORINERTS, Sia he fer, Bel rs unlike chlorofluorocarbcns, are unlikely candidates to photodegrade after adsorbing to send in spite of the strength of SiF bonds (55|. BE Tm The literature shows that increasing the number of fluorines in a chlorofluorocarbon greatly decreases its rate of photodeoradation when Somme To Sh pe Re he es adsorbed to sand (39,55). Th6s, one would expect Se hen Se ina ihieorrats Tor Es that these completely fluorinated compounds would degrade even more slowly than chlorofluoromethanes. In addition, these experiments have shown no detectable C-F bun4 breakage. ~anno has reported on the sensitized photodegra~atlon of Freon 12 with very high fpiemoneid ShEoTnEiEcEn concentratons of nitrogen oxides in air. This study, which used a xenon lamp. shows the formation of HF indicating breakage of the C-F bond (56). Similar sensitized photodegradation could possibly occur with the FLUORINERTS but would likely be at an extre~el~ slow rate. c) Effects As a class, FLUORINERT liquids show little aT aplac Gtl isen tot2 toxicity. A summary of the environmental effects data on this class of compounds is shown in Table 4. No significant toxicity has been found. All of the thirteen FLUORINERT liguid products which have been subjected to acute fish bioessays have had 96-hr. LCs0 values greater than 1,000 mg/l and are classified as inslgnif~cant hazard*. *Appendix I gives a scale rating aquatic toxicity data from highly toxic to insignificant hazard. awsoeses 3MA10065499 pp 3M_MN00000054 22557733..00003377 fBn aaubiinliontoneCLnSSRENHEEeLaut conx TEE vee -~3322-- I~,,/T~ T.... ".., . T;~I.A~L In addition, one FLUOBINRT liquid (co 742~7) was 2mfgo//u1ln5)d,, tGoannadb'e fcnooouunrrtovwxeeirrcee tffooouunnDddaphnnnooitta ttoo~LCaasdd0vveerr>ss15ee0ll0yy affect activated sludge microorganisms. wveay mane LR 4894 mes L~ 3844-1 wes LR 2465-i a mLwR o7w9n82 s men L~ 6589 swe 12 7842 sa 12 2455-3 cr CC 742-7 amieTypical fur Boiling PRaa~gjee(t~'C)) maw 138-189 ~LE 4 some orpumosms.on ~ OF D/~I~AL Z~'~TS OF LAson. exefSrE Een Major CCocm~pnoenennttss cm wae am Cts (C4Fg)3N Other Data 96-Hr. LC50(a,b) and Lab Request im(magi!l) ) oorr RReeffeerreennccee 5,000 >1,000 >5,000 25015250. 2455 was 139-185 ws 165-185 ee 139-180 mes 207-225 mm 203-221 wm 244-262 wa50-60 mm 99-107 we90-107 F 2 che ase {C8~17)~2 cu fe CIIF24 0 cm wa em {oC4Fng)a3N wEsH soe BE -- pHue-- ensis C12F24 (cyclic, 1,686 1,893 >5,000 >1,500 >5,000 cw ee 1I 2maee ttn (CsFII)3N corm, : so BtAeS soSntsieereisa. C13P28; 4 BA SE F2~F2 ((CCoIOPF2)1)FFC~TF2 cn am ow (C6FI3)3N ane wwe ee C6F14 asngos, imo bsitaoee tums 8FI~ F2q"~2 ~C4FglFC%~CF2 ane amma es 8F18; caine . (C4F9) Fr~O,CF2 >i,000 >1,00o (h) >I,000 >1,000 >5,000 51.000 >5,000 >1,000 4894 DfFiuidnnggeanrlotggrrseouawpitpnhoi(rdt)).. 22445555 Retarded activated slu~e 02c~emletion rate(e). {ST), 2465 No a~h~rse effect on lab scale treatment system(f) ~571. 7981 No effect on activate~ sludge 02 depletion rat~ EAI 79215,79213, 6589 6589 7842 DiO not support fungal growth (d). 2455 s5C5o0>1,DD5aa0pp0hhnni~iaa/..I, 22444585-55Hr. Eo3MA10065500 woos 3M_MN00000055 2255"7}3'3..00003388 ee a 3a uTAl pTeEn ee rate miroso)re, stot cToEmeEmees n Product wm wo q fy Sa Seaertetd tR y ivee s sis 788-19 T~ical Range(`C) 50-60 (Table 4 ontinuec]) Components 3 pr te >5,00C ooexrndRRee~ffeerzle~~nneccqee~est Retar6ed activated fa dna ~eDletion rate{e) ~ ac~verse efect~n lab scale tma~nt s~t~(f). 2455, 5713~[ Gen ww ome ue on 4913 cma ww aanmee sta 50 sete an esate E09--21 90-107 75-90 Fetes: Raas Sasa Footnotes: : Cyclic C8F16 C7F16 >1000h >I,000 4913 No effect on activate~ slu~geO2 ~epletion rat 6262 (0) ALL 6c. sp tests wre on Fthend irre (pagales Emel) wees dicated. All 96-hr. LC50 tests were on Pathea4 minnows {Pime~ales pr~m~ias] ~!ess indicate4. (1 AL 3. 3g vlons are fox rermicible inten. All 96-hr. LCso val~es are for nommlsc~ble m~xtures. ( 400 3 ible 12 5120 argent. T 1s meu of savin fps of pec 5-4380 iS a possible L~ 5120 ~.~unent. It is a mixture of varies i~s of ~rfl~ Sram ~i tetr~fu~. 611070 3070 gr acing wae 1 icin spa rd sentence nei ASTMG-21o70 growth rating was 1 in~i~ating sp~rseandscatteredgrowth. The analyst a a TT TTIE De felt this growth was dU~ to a mass of spores ~n the inoculum an~ not t~ ~-owth on pro~ucl (0 Activated side ines Moor with + issved capper centeotion of 7 55/2 had Activate~ sluc~ge mixe~ liquor with a dissol~ oxen ~ntration of 7 ~/l h~ a prisms fog ariel veges slightly lo~r ~n ~pletion t~ ~ ~e ~n~l. et Sou ama etivertaas orgie ~is ~s ~ly ~t d~ ~ t~ici~ b~ to ~e fact ~at ~rfl~ri~t~ o~anic pr IE el iy iy li~ids dis~l~ la~ ~tities of ~n ~i~ ~ey ~ tra~fer to ~e ~ eT BS Ee ~. ~us, sin~ ~ve 02 ~ p~nt, a Io~r t~ w~ n~ for i~ utilization. (6) 18 M651 100 cx 760-19, evn at. reasonably high conanations (13 3/1 rrmdocible LR 2465-1 an4 cc 788-19, even at unreasonably high concentrations (13 g/l no~iscible ee eo Thies Sl Tr Are: mixtures), had no a~verse effect on lab scale semicontinuous activa~e~ slu~e systems ae operated for ii days. (61 1430 10 0 ossiie 18 7981 cron. L-4308 is a possible LR 7981 ~q,~onent. @ Slotis smi (Lapis sash). Bluegill sunfish fLep~m~s macrcchirus). TThhee llooww ttooxxiicciittyy ooff FFLLUUOORRIIHNEE~RTTeS lliiqguuiidcss,, indicates that this group of chemicals presents a Ee nT ernie an ~nsignificant risk of causing a~verse environmental effects to aquatic organisms. The low aquatic exposure resulting from their low water soluDility an~ h~gh uolatility further re4uces the r~sk. suntossssor 3MA10065501 Suvoscnocss 3M_MN00000056 22557733..00003399 ae -34- 2. RReeccoommmmeennddeedd TTeessttiinngg p~i"'' ", ,I,-A~.~L NWTToiooScolloraamabbetoonarrdraaeettdoorsryty3utdssytthuuihddsaiiseesssbienooenen.nFPeLLmUHUcOoOuvRRbeIIivNNieEEsrERh,TTeeSas.hLLiiaqq"nuuTigioddogssisngasactreeudy is etESlinhnineaeatcvsbbreeelleraiiansntncsegughreentitiithhtesesesattuEuEusnnnnd:yddvyieierrrrhoossannttssmaaeennbnndaettiieaannnllggeoosLLfftaaabbbttoolhhrrieeaastthoofearerdtbyy.ee ttoasoTnndhdccioosennefttffiifsennetccuuutteadssllyllosyoiffs 5. Lowitheascetocshemaincealmse.ss saree L1.ow sMeWckAcgirdosunaand Their Salts 1. RYB~ck~round ---- a) cSCcPfoolheemmayesmmssseeEirrcaccaSc1iilooaaannsllasPiirssCicotthnhpeeae"msroociffttccieeaattsllSwussooosFDDf.liil)svvuoiiorsrasnoioigcoco.hnhneemmmpopiirsrccsooeaddlluuoccfattacsscsiihddeiissninsttshhaiilssts. Ea2I(onc2c1kio8idtc"nshh8gee11aa0rrutn-eanhn9enenevvuueaathtrnrryrydyataialsscclcttiozzrroeeoo8nddnn0ssg5ll-ffSIyyoo)arrmmvaa,.eccaciniiddtdtaihihtceecsso.maFafnenlldduuBoooorfccovooocercrthvrhzheeoeoenrsmsii:iiircvcvaeeass,lsliacletps.t mUTioanhukTiEtanhhge0betcchaasnesemeeutohoraffazlaldraa(drrsoggeueses ss1mp5paiitlltellhesrsiaeoolnrfsv.iddrliossnccHmhhoeaawnrretgzvseeesrs,,. they except they wCpSBCoarraauloollcddctduuuucleletatabsstteeeeddstonuueJgmHauagnetnaeenrcsrrayttylG't'isiszatpehdataLLtraaewwisntShcceeootrhy1nnhesswVtttihaeaulennnlvttissarqEuoulffhnatoomatrrieimtncattetthh.eeelsslyeey merl$inieTgvqriuiuairo6tdonsen0n,meetnnotTtthh(ee1a51n80daa))tt.SmdrtoiosssepppUBhehnrTerelrsirkeekSeeeotvwiuiitnnbllheillet1henin"TeSonoyatetadrqeotubb.Feaetffiliaatcuuhooessrrriiosoggccnnhhiieeffmniiitccccaaaannlltt SpbPEsltriiroTnoookcodcd.anuounacncctictaseysTnnhtetaateriloaasshtteioeseg.ohimslaaiiknnkweeoassrt.lTeiirvvsttiihehnnseedggmniomleuusLanbynymtsilsistliit:eikkemteensyllsyyooofrrStoottthooesbbeoonnde 5) tsetgreoandgaltyiotno soil or sediments. b) occDT(xCoeREygODgDr88))ea00nd55-a-iiIGt1nneionsas3nahhnoo22gwv00ee--dddd(aaCayynnnoo).ttbbaeiiss(ooteLcAchahaneen3gmmd6.ii5cc5nn3aaoo.lldiiooccxxShhyyIgrtgReoeoLnnmIraaattdcdeeaemsraaeccnnshhddueelmmtiisccaall oowcCExohheyueeteglmmTediiancccaaabsllednaecoSmeepxiaxaypnp1gode0teecnnetc(ehCddddeOeeDm)nmiffaacoonnarr(ddlLRccaSccsueu5gqg68$ggt911e5ea11)ss0d0.st-a5s9st..ioeeSnxxittTmThrrhiieeeeln.mmaeerlLtaahcecrkkesuooflftsa& vreisriosntmanecnet.to chemical degradation in the ettects environment. c) EEPEnrrfvovfiaeirtczotoonsrmmaneennSthtoaatlls' pTriomdeuicgtnsicischaonwts sshcctharrheteeeneeemrnnsiitt)nnoogg hh(ddaasaavvetteesaa TvvoaeoenbrnrlyyetthhlLeeiitttanntnleeldeuuettrrAttaapoollpxxiieiizzncceediiddittsy~ AIll()~ii.tnnEhseaidTlNgSienituiyytfETricaeorralniStzZaoetnodhheearsrzcLactrstdReo80)a0xi5iSsc-c(IisEaeeefCcffaaveTSutccaseettbenssslde nntCtsoooo5 ncafaafencciidnsuusthtthreeAiapintpnieon29nd66,ix S&C72a10-a5" acoundh minimum Tathalicys only two of hrs. at 2000 mg/l. At this same concentration, cc 8110-9 caused minimum lethality: only two of 60 fish died. awnioosssoz 3MA10065502 aw moooncs" 3M_MN00000(357 22657733..00004400 EE -35- 3m There HSTTTshaailaavbbugotelldhegeeeaernso55mSnhilasHaacclilhnrssgTaooonoiOviatrfrssoigihshuoacoaosunawwnminssiestaomntttssahhsecaaeeuttaauitttlsettycchhoeoettnonoocccnxnreceeieinunucuettrttiirrrrtsaaayayittllniiiitooz+zo2nneessdvadaaccsstmaattuiucciecvciivahhddatssteed = Thee higher than would normally occur in a waste ThStathhrreeaehetactllormotonwehvateniyttttnootaxxserliyesccitnligetelTmyyie.nkooeoltffl"yycttoThthooeneSscsTeedeinotlcceuthhstaeetmseeiicciiaanrillnsstt,,Fhheeitthhhpaeeequtunaffttaa1iicc1ctctving eovTSCFonorilvnnuinnemreonreonnassnllmiimeSavvaniiErktnneteggrssaensSsdyyTtsshhetieneeomrtpEiEsare,:oicbnotaanaahnbnncEtdidealnitsttitrthehyyaeaetirioeorefoillfsniooiowwmgeeinippsitrrSfhooteiegdcrauaoaccmnttlstiiioovnning arioLtehdEemevSoaeTtriatEesrpi:.eppEaasrreteeN"fnnSeifettveovecnertce:rtesxihitnesrefleeirenmooseeemss,,FrtehesssisoosiinmsmettgtarunccorcooueennpcceeooorsfFfnnctthehheaexennsiimeessitccssapBlrrssoaohdbsouoeuucttttss 2. Recom~moenddeegdrazdaetsitoinn.g NNRSooeecoffemuumrrettpnhhrdeeereradueeetnnTsvveiisrratootinnnmmgteehnnittsaalltintteee.ssttiinngg 1s is recommended recommended on on these products at. this time. meus ~BL~ 5 ocroF on vemIzED FRR ACE T~XICITY OF NaOH NEUTRALIZED ~CAL AcIn~ en a or me Ser AND OT~ER SALTS OF ~ ACIDS moe roma Product Formula ones coma cc 8110-9 3F7CO0~ Testratiens Ein Neutralized C3F7CC~a wast cron cNcTeeu8st0t5rr-aa1lliizzeeds `iy CF3SO3H CF3SO3Na comes crn cc 786-6 C23SO3L~ foLs9EnCeS-sH0er.e. s-:n >2000 ote a>20000 >1000(c) sL MItinimcherirtobbybiiitanaislL on TI Ps = Concentration 10 i, - >i000 7364 - on >1I00000 s5e69s6s - 4388 ccce W79I1-T17 ([CCPF338S00537-)] [MHH2ANN((CC2aHHss})22]+) >100000% -- 4h74a0 (0 bionsys used Fchess isos (iseprles proms) snies indicted. {a) Bioassa~s used Fathead minnows (Pimephales p~Telas} unless indicate~. (5 Gomcenteation causing an irdiate rection of activated shige cen (b) Concentratlcn causing an irmediate reduction of activated sludge oxygen ry uptake rate. ( Bhegi1) mntioh (tein sacrcnic. {c) Blut~ill sunfish {Lepcmis macrochirus). awar0065503 3MA10065503 aN0e0058 3M_MNO0000058 22557733..00004411 a ---- c. sersctants C. Surfactants ww-36- Ga aL l1.. RET pBaacckkagrroouunndd ---- a) W tBEFPaAehasIryteEescr8ri0ec0sSaSso2luol1onlPTnut[iriCboaao8iiptEelFcie1tsTyr7RstSeioe0-=ss3BnKLut)Rra} tawd52ce66eir22rea5e3ntss{(Ceetcu7doFdairn1tiy.e5isCdac6OhoO seoanrsNuaHytd))eaannofda ASerFFnleoIvvupEhSiorrirreeooeostnacmemtehnaeeetRnnmralttitcsaclsrllavotleissppoeeFbrCrPpissrrspposoteeggueccrrryttaafiimmavvceetPpS;,aaainrrnttStbcsooektI1hhinn{1ipp22srr,0toa33h))ddes..uiececFtdtaysstFF.errhhooaaomnvvfeeaann mEPEhTeA6iiTIagEsshuA8trw0Oeea0d2tE,,1ersassnosaoSdldououlslubSdbieeilttlieeLitrreitymyhtyiiy.nhnhaeaessdmseSabBittesnooeeucenersbeeemmntooaaahrrnbbieetosouuttaavsactcsucc11duu,.y0rr0,8a8a00tteemlmlgyy/1l 3sssS(iauAu5etbt9bi)uess.nrreigaaqgttuueeTeetdshhnneittsslliayyEsmnsbpvsocililooeezunnobtonoiiinfflereinmnt~eZItyAddAaIlmbbyeyB8.a0Lo0sttsi2uhhns1eeroeramsasnaeeennannattlteloy'yrstswstyoiaoisssDDcooovoffhnercimhvaaaaanncwvnniaaottneerr SER Sor sat pene (651: during the Environmental Laboratory's evaluation o5iALlMfR8iImEia"5t5t66h22ce55naiwramspiiosTannOnoOnovvttgeerrevyyqdGaueesti.ssoepoorrmllsmmeuueiibbntnnlltneeeeis.d.n(,.a6t0e)II.d"SttssSoelaaufaalbsccbiettliuuriisati)layhssssowooololrruulkkbbeiiloloniniwttayys efcltfqoohiauuuioinanstntldoctwoTvtheomeeipeungotgihueoeetntndmatl(BulywD6yas1)su.idaititsasescsSErocoomleiliRvununeetbastiAeliidninaTcttaya8fgvdtvSioaeoltvrlRuaesmnmaTeeonsIonaofomfeTptuwlahrebaealtrceewera3sM.ooff TiTEEfhhAElRIeeurssoaeerR8co0otc0hhba2hiian1egglt,mhhsicvwLIaavRaRlittlee53lrr6s522u53arss",ifoo1allicnuauttnbbedeaiinlltioioIsttnttihhieeeeasrsrrsqeuss3sIgMtnuuiigsvFgcfgeeilenssusetcotmrrvioonittccchhhhTaaoeetacnmmbmiilaccenaaclls6. wESsIiun0o~rt8uthof0nTaicZlsstieeatdItnimnlmtaeestenictrwpas,iar.lrtltLliiiCtdpbliTiiiioodlshnnueiitstSnneeiiggsmSsioeufnFecerrssaooa,,mnqauioaotthsrtvheeeicsswyvupaasealfppneeeeevrrnnai'ddrsepepoeddhhnaamsseteennatts oaStSqrahhCugteaeasemnoenequiuiscsHfeilhmpButtahooertarrsatsooseetocrehh.edidmumioirincirctanaToilghlseswswvaeaasaacsrrtetetde.eeawwtval1aaatiittekkeeraeerrlll"ysystoltiurttadeooisgantetdrr.nmieeeecmsnnaaatttii~nnaanntiiddhnnattnnthoohetet to concentrate into wastewater sludge. 22657733..00004422 waioasceos 3MA10065504 a3N0000059 3M_MNO0000059 22 - SSOOLLUUBBIILLIITTYYbAANNDD o OOOCCChTTVAANNEn OOALL//TTLWWAABAABLTTLSEEEEoRRr6e6sPPeAArRRaTTnIIETTIIPOOrNNoDCCiOOcEErFFs~FIICCIIENNTT$S OF FLUO~OCHwEaMtIeCrALsSoUuRmFiAnCiTtAyNT PBODUCT$ 2WataRteBooroommSToTeleummbppi..lity rReetfee rfeennccee oacLccR5r82sSs40oa51on6n1--nihi2a3 i >si225500 a1 wren (55.500 cpEccctAIef387908Ti520icd--0os722t)31nyerany soaner I>13I005%50g(0/ga0l)/8l 3 jJ(6it4t} 2cLLiiRcRh 805-10(hydroxy es 2318-2 3P2i0 e 29~9 : foamer) 21S(a0af30)oagon/tl o(glgee)nl)) (((55c66a)) cc 773-588 i 32s LR 5625 SFE a. LR 2337-1 50 g/l (gel) 3508754 >500 g/l 353H en 300 g/l (gel) {{((((666se6165an])) SW cc 7711-18 cc 777-3 1 i g/l I g/l {b) 5(67) (68) ml - F~(a3o))otnoBSStooIellsuuR:bbiiRlliittyy iissLuunInkknnoTowwnn S bbuutt pprL roobbaabblR lyy hhiigghh (0) Sbaecause it is ) csrolodueyatsolution. Cloudy solution. "7 Gcionol iter partition Contsctont hn emoOcEEcoc~irr~etaeeefiarnfnooeeiaoclcicc~h/iiczeawueu~nartnraitatatni,teteaeerrllli1yysspP.,saauararvrvttaaainaiinsaittoicoliiceicaoobtatnbnenalaeten.nCc.oooeleeff/offooawrrffraiittocc3Seenii0hrrlee1yynn1ttSd3Sioe3hns-(ceetKlrAo(inwKu)bos,uutirioooo.rn6n8). dSSSfpooirlheenauescsoeetrnnoooccetthceemeeR8ixxo0ctii1aass~ltt-2233asassurIiftatsahheceaantn.assnaaiotmmon,eeniici.cscscooelrmmueaa8ltttt0esee1rr1i-iss2aapp3lleecciiara(aeennKssddo"w=iiitn0nohoiu5sntt5hh)ee. phpBtiaaaawrveobkteesiiittmnmiioomoottinnscbwcceieooebenenlnffefefEiiusuccltoiillleoyyvnnettnds..teesvv*ee,lQlGououpaptaenehn~tsitisitfftaooiatrrstiivvniLeeooot~rSSiiAAceaRRsstmnppreeeuetccehhiiooeodsdrss hSTpv(hiia2ee4tls)uht.eyaaippopr pfnolLsriiccaaCccbobiria lri8iei0ltt1ay]yt-i2oop 3nffgFttthrhoiiyssep sxiiddcsiietssiittonrre cgiipbbeuurntteiiigeoornl nnelssrriaaaonttneiioo NMe SceeheqveumeamcUrtos atidyhoynTennalsa, nemsiicIscco,rrppNerrtTlhohoeaEppteeirsSrFnteeegiigsieertssepelshesyai1istsstoionscnqaouleSeeB-ssqaacttuehiiauveootinmnnitiaoatcbnhblaieleoso..ffataBaBnadynneecrsjeeee esSSteoeeilstuailhbeiitil(ii~2oet1nyy)., hCehaarrt.foemtatk which correlates Eow {S), appears to make arSweirsHteshaoIsnwonasTattbel,lree oFoeadiels BO prediction. range as the predicts the TRIES onl" IIS Using the midpoint of the melting melting point (69), this equation solubil~ty of cc 8011-23 to be 250 ~/i. a Sez Solalaa lLily enti IEiRne iSng SHisoRcleted BiIcRe in thesaveows *co 8011-23 will exist in the dissociated state in the aqueous phase and primarily in the associate~ state in ~n-octanol. awtcossens 3MA10065505 SWN00000080 3M_MNO0000060 22557733..00004433 a S011 adsorption-2ceo-steictentsJ - Soe il oHxEganDircoIrNTweIAL S635 and 45 For Ba1 60021 (30) indicate vary hish Soil Adsorption Coefficients - Soil organic matter adsorption coefficients, 5625 and 45 ~or EAI 80021 (70) /no'care very high hI fn nen ta mobility in soil. This is congruent with their TRL eins high water solubility. A regression analysis Lh aS, er BL aaa, ILL based on data for EAI 80021, LR 5625, LR 3844-4, SECTS SL SR Ss rastioneris and LR 4197-2 showed the following relationship Be lami (a) hms sart oRpinde patter between solubility (S) and soil organic matter mnt aw adsorption coefficient Los Foo = 3.38 = 0.513 Clog 1. log KOC - 3.58 - 0.513 (log $), Ihis repesssion squstion 1s geacly Wgneicad to This regression equation is nearly identical to EheeSEEIation Fomereed by Rerast and the correlation reported by Kenaga and ShreTRI Is Kan Ggring (I0} for 106 organic compounds= Jon Foe = 3464 = 0.55 (10g 81. log Koc = 3.64 - 0.55 (log S). his prelininary correlation sain supports the This preliminary correlation again supports the Pret hat ad Citrenty Se5cr bed isctite prospect that some currently described structure EETionanin: hey be. sept ichbie: so Flacrcheniont relationships Bay be applicable to flucrochemlcal SHE surfactants and alcohols. Developing soil thin-layer cheosatosasty (7Lc) Developing s0il th~n-leyer chromatography (TIC) rs plates with water is another method of measuring BEA SE Caan tite Ee heocaiiral the affinity of chemicals for soil. Procedures Rate Seer Flopcasd by She USEPA 35 sensu have been proposed by the USEPA to measure LEE, Tail petias TTEoS mobility in soil by this method (71), and To ieitats messusaiets br spore alelis; petted prellmlnary measurements by a very simila~ method BETA Lar SE Shokd SEE Seni have been made on EAI 80021 and LR 5625 EatSetommestes She booms ot Bar 403s sporti Unfortunately, the amount 0 EAI 80021 spotted ip ipa htt yl was too small to allow visualization. LR 5525, Fede ER J ra TI however, showed lo~ mobility. This finding seems rater oth che sek aasbrption to contradict both the soil adsorption Le ent shu SE na ene coefficient measurements given above and the Farida on ol che predictions Of low SOil sorption based on the Er Sat SPH Rh high water solubility Of 3~ fluorochemlcal ha Re Lett hoe) Ths he surfactants. These adsorption (Koc) and TiC Sinn LL Crh sont measurements were conducted in two different soll Treas EA aT Sa Factors can couse types, but while edaphic factors* can cause 4mne totlouing sxe sgaphic factors which can atfect chemical *The following are edaphic factors which can affece An mobility in soil (73): HB cipieieion sien organics I) Complexatlon with organics Ee Tadhines Sith Scsantes a) Cation exchange with organics 3oSR hiGenltaons 2) Adsorption by mineral species fe.g., clay) b) Organic anion fixation ) Nonp~lar organic reactions 2) Adsorption by mineral species (e.g., clay) 3 Remon 3) Chemical oxidatlon-reduction effects 3 RELI 4) Precipitation reactions .and pH effects 5) Ion exchange reactions I es a) With layered silicates 3 HE Ey SE re same b) W~th hydroxy oxides of Fe and Mn Lo3HME emNEaEeD ncn) or natura) c) with organic matter chemical d) With llme materials (agricultural or natural) awntanssses 3MA10065506 aw noooueont 3M_MN00000061 22557733..00004444 -39- M AL adtEEhhilifiifufsseerrrom emceanahngcgecnenneiiissttucudadiineien cascahtuhreeeretnmaiuuccnnctolaleliiIknkteemmeloly.yb~iblw viiCiliitittthyhay,c,itthgdheiieifsctsfeeafeetrerieonnncceeosfs ooff Shoe data is nesses. Eluorochemical suractants. Clarification of CoBBthlnieoodsssueoocrrt~pdettadiitaooonnnis--cAAeneebb80idl1ooe1ssd-oo.2rr3pp,ttiiootnnhessGttiuusddyythahhnaassclabbseeieennne salt TSncofhefEooe"unpndpeduefEscrlutfurEoeloorvdurtoooocrcr6thahonoeeenmtbctiihichccynyealdl8llce0y1yscp1ctpl-oloro2roro3htntn,eiiegxooxlnyynyt]lhoeotffsosduualilttfcehEhiiottossnhniiiavmcmcnaaaotttle8aeeadc1rrmidiifsdaalnlule({d77gvws44eaa)a...sslt TTCTffhholloeenuuuanooidrrrrnoooecscsnhuuhoileienttmtnsisittcchoaoaoelfflbaignptptudoohhcrriiosttssuiitsoossrnnttoupunddhoogyfyaflsyeciciccnntddodui8i8rc0ca0ia1a1Cntt11tege--i22v33pattahthtaeaiitit~ssagstltlelhihiueekkdeeglleyy. to to bSEhrteeehhumhhrrsaaoooivuvungiigshoohirr'minsiao`lofaawtfrashsetttthhteeiioavssw~aauttteawheeoaatrrtuteserrrttprerhsseegaooaaisllttceuummtbbeeellnn~etedturisfffsnollyygrsuuttooeeprrEmmaAoo:.Isccshhaee3gmEn0Teivi0hc3ece1aallaniiass sE~EtaARAh7Itu'5us586r6082a200s5t530i,,e12md"1i,laanan~(sdr`ttChhgebebteseocucbplaaeetfuitrhossfafneetiliuvcoooopfrrfrsliecnndiiiatatidsetct)ete,desdsdiipptmmoiohifrlrelotataririrfiooiEitnntAnyyIdii1nsstt8goo00aa2all1dssdoosaanad Sredtneste tal preatetion. saturated, C~ sulfonlc acid), credence tc this prediction. the finding adds pESBSeeetttrcuutdfogiivtlleeeuusrsoorrqowwauoiicatctcnhthttaainnrrteeaaatttssssiuuvddlleoofflnnooeyennaattbfbeeyyromRRiisisikkteeivvrrseesrruhyhyaeavsvddeeiiaffnfssfdhihiooccwwuufnnlletctettshhttaooatt oSperS1oovuelfleecanGanornrvaUwechorhoeerer.nqng~uaaanneeinlixnxtccttirrttaaSshaceooctllttvviebeeevdidnnecttlobbssysyy.. vfa3arsoPssFmeeee3rrrr1iifftee3lliss0ussosoouorrfeffooosoouccnnntdtaooaannnnndpptesooollfaaebercresttoo SpesH(3esu7B5grsl)gtfeS.niontnvtaioiTtesraheioltelolsysyieetnaccnoott"stmmwhhpopeesllueebfElttliifeeennolldddny4yiianntggbbwessooauusmnnssadduuaygglgtgsteoooeSsisntstsfdooolluttuusnhhbbdeaallttreeotnospplrrbooyetteetiionnss apnaSRnoeoRuinrnEnmsfsRtaoloeillul"euoUtFrbtilooliTeoresacsttuppteaerrnrsoorettaaeeannisi~dnuntalafcciieooennennooaursutsooeseiinllvmsssmiaaacttoyooaernfrrmiibeaaissnllneetssddd.,,iimmseetbbnnTrootthtotssehhnsgeooliiffynn to tthhee CcaEfooqiiannunnnttdadorirtirnaaniagrgrctsyaycoyarattnnooddbtatteshthrteehherdeeespptboprrnrrereiededasidwilicaiccttctetitieriooinonnovnsnisoesroff-lobnbuamabttsesihhneeieetddi.tEEoyonnnnvviiTrrhttooehhnnseemmemneennaattrraaeell Laboratory based on water solubility measurements. SVmVa~nEaeyppaBoosErruoitrrhepPeemrrereeensnststs3ususrreewwIeeir-rs=eeoNNrooomncaadshaaeeeccattuuioosannc]lalEEsNAvvTIaappinoo88rr0000t25pph11err,.eessFssaLLuutRRrreee55o66f2255,. oorf bSbFaFFeenll'ylumVvooeoetorrvrotoyayhccnehhereeuunnmsstiiee3ZccfPouaaallllnf,,dlSSut`thoShouurUowsdoswecyycevhrveePpiermaart,,criuetceaiiilnno1~s..npporrifeenTTddhhiieeatcchttepfciihaanneFrrggmaaaitmrceeettahthtleeeoefrrrraaccttaaenen bSPobafeeqp5ttuenwwamoteetoxieeivienncenmaeetnttnhhnveteevisitrsaaootntnnndzmemmooeessdnnppaitthrstsseeterrresi((ob44faa5u57nn)t,,d~vioonelett.aeer9torro.firr:,leesisettzvvrraaaciitpphaaiooellorrmnicapapannrrflddeerssossmuurree a3S apq3upaerooouH uxssimasstooellsuuttiitoohnne oorrrateffrrooofmm vttohheelataaiddlssioozrrabbteedidonssttaaftrteoemoonn so~l (76). pLuir~2nneccshh55s66aau22nnr55@seeeddccaa(7nn7{t3bo.bbyyee ~Tshs)a)uubtsllaattitimneei11dsa776~cscCCoo.emmappa3nllndedebtteeesaslltttyyamhnooissaaynnpzddhheeenrrrrtiieeecccccoosvveerrteehdde CepeSinnxrn0eipv"siePiPsIErTruEFoioErEnenemmneecmmnneaa(ttnn7uu7if)fnst.aehhccherttaoouunuu~rsdgcoeelhhs..itnvvgooLOPOllnnaFaA5ttI6itit2hhil5eeii$zs0oo0asp2ttttr1hhiioeoeobrnrnasbnldhhffyaarrnnoosgdn~er.,nytiiieoonttrugssusr uutssoteehe aSennxaaplleyyrzzieeenciTeet bbiyyn TThO0aCCndlaainnnddgCCLLECCAI iin8n0dd0ii2cc~aatteeassndtthhtaarttyiniigtgss to Mk10085507 3MA10065507 SH_N0D000CE2 3M_MN00000062 22557733..00004455 eS -t0- TIAL -40- v1IVinanaad8pppLiooocsrcraatpppteerrreaessstthsssheeuuucrreneeneeeeaiisddnsdpfpfovorrororolbvqaqeautnubailalynlyntitizqqittauuaatiittittLeioevvneelloofwr~vr.eeo.sanssouTsTrahrheaueem sesseoeeensntsddtaaototaaff 2hyviitteonntmetnhtaat)wialllscetnisbubtlieonp.resicelons of vapor pressure and volatilizatLon fro~ aUueous systems that will enable predLet[ons of environmental distrLbution. b)) pegracation OPOpEnneeoeerrrtfflal33ucuMeooarrEfnoollcccuueaaoo:rrrrbbooooccArxhhiyyeeklle~niiiiccccFaaAlLlssaallss8ttu0u:.5rr2ff1aa,cScStteeaavvanneerttrre,,aallLLRooRff5566tt22hh55ee,,seeiiss aa pSSspsuueeueccgrrrhhfatfanliciauastsscooa-rrnsoTaLtmns~ssiuu,dli22eft99o22ol9n3dn~Lekicetcsainn~vdaEaeAccsiittiddhheve8es0ssa0ahh2llyy1ttodd,ssfrr,,ooxxafyyralaennuddoffrooaaottmmchheaheerra,.nrrieecsmamarataelieinnddeerr,. oShBstu~euhiligrlssfaffonoinniuali~coaccc-rttaitemneaarlgcrcidtiddeeggssdrr..oo~uauenpprdlDDmveeruauggns;srrott~aanvddfesaalssebboepiioplaltaoiriirftatnaytyatfetellaelauyssysossrpeeoccosscoorsshnntmmessieemiionn~ddntcteessasrr.loottnnhhee perfluorinated and nonfluorinate~ portions. SBBiioceddeee~qrrdaadsIaaettiid3oo%nn) --aiNNneeoiinttthhhee.rrshEEaAAkIIe8800F00l22a1s1k nnoorr LLRR 55662255 sdsb{BeeeRiipgp6oGaraedararieuada1ggtietrredeaawdataatitnrrtrieeleosao2tntnf-nmr1eeo/ssnnn2tttt-uumdssosiiysneeysytssstshettmeeuusmmsssisshinantgkg(r.e7e(87aif8)tnr).i:1oonaccgsuukTllTawwaIoonffoorrffoommtthhtteehhsrsreeeeee nPCifEoaonllpnnouuaaacoobccurrlcelooelalcciihhomneewfaamneittircgeecearddalolfwrLiiawonnnasmoogsccttuusaelloyssanas.,tettthmoaoaesnnsddhheaa.tvvttreehhe{uualssmmtuiiiomcnccmgororocroorheeoo3errMmgglliaai~cnnkkaiieelzsllsyemy.sstthhaann ETbcBFRhia1liTpo0osaS~0Sberelwgawseratatsasha~aocnafattitthhcigieeaorolnonmmwooisstcsn~teaugssrttirroaiinscegctvoovaerrtenroohtuuessddss.ooennlleeaafObblotooounnhrorreaaotrtttcoohhhrreebeyysbimeeoidceaglrsa.dation E2tf~RnAealEd7ssuttossr83I,,R0o00c223hiI1~6enn2mcc5~ilfcuu7agd9()liiL1ons49ngas)"nu10ndaar35f8BaB3S4Oco-o0Dthbh)ra2s..n0;tasWBltt.aas~errossbbttuosssOruhtgrohoovnenersssttbbuuoobdndtt~yoyhhodooeEEngnAAIrad88a00t00i2211on adSSneondggareaasrLddo~aabtti5iic6oo2nn5c..on(dLiBNNtOoi#ot3tn8ees4ss.4tt)ii,nnggalhhasasos sbSheeoeewnne~d4oonnneoe uunnddeerr anaerobic conditions. GTTEbhehllepeoosasddeeneedggeredddaaaatdctaoaaanttiiaaoorrtneneo ooaoacffddceeuqqEEruAAuITaattieen880000att22noo)1dadeqaeanmnumd~oaontnsisLLtcn8trraaeS5tn6t6ev22e5i5rttohcchnaaaamtntnennnoottt. bbee TFdTTthohehhir~peeseseiirnrsdrfuepeepdbescesriirtsfofsatlnltanuvanotontcrircoeiiaennlOaalcttctyocoeeud~~rdrueelggssLerirtnrarauudodacucaantttttuoiiarrooqteennhuddea..tiisispcosHccshoooeoiwnnnvnessvaiviiivlessrerittor,teen;ynnmtettEnoootfww.iitthh moFSPbofotiirroeGetdd'traaaeuutsnggiuashhgbnfttasoseertrfrroamvon.aptpralrEitriyooaiaodalontusnlf'ecyattaavnssnroddur.oloieffnttghheoeuuunbntkkiccnnooooodnntwwechcnnegoormnaiipttdtocooaasaxxntisnictiitciboitinfftylo0y,irrhtmsoyaattstteetiosissftctossnnta ~pFoeerrteftoorrrrmiaegsdo..rously favorinS biodegra~ation should be TTfFnaallbbulellooeertioocc77hheestsmnhheiioolcwcuesaasllbba5iissoouuddrrnoeffetgaagcrcrctataaodadnannatttttiaioioppnnnreoodddGbusaaictetotaetosse..gooznnadoToTehthtnehehieetrrpprroodduuccttss oZ3sFif23noe1altuvttseehhbe!nen~ttsssEsfualtWwclauhhhbooilirreccooahhccsbh~eaotntmneeoiinnn.cc~odaatllttoocssomeunmarrtassaifkkiaanccttttaabhhnneeittossdbbeiigcciirncdnaeedsgnAaeroebaannlddsseaappbbeeiicclliiififititcyty tests, such as BOD. Mat0085508 3MA10065508 SHNODO000ES 3M_MN00000063 22557733..00004466 a1 = -N TAL wTTSSihh0Ltee3Ehss0ee2n0odcnaattnEoaaoRnEni[ssilhhAvuoo0oowwrr0iitt3nnhhaaaattttaeendddfElloSLuurhroogp~raaoo3nn6cci3ihh5csee.mmiippccoohaarral!ttviieoossnneuusssrc,.sfaeacnce6ttt..agai9n.na.,ttlsslycccc nnC8iToo0oaS2nnI-biEi52icic35oaoa,lcciTlhhl,yeeyEnmAiih!bbcocooavann8)eldd0ee0dsBd2oO1xxB,yyoS'gsrESee.ggannaanncndJidldcceeoLsammsR,saaenn5dd6tiL..2o.i5ee,.t.,TThhahhtoocacsscveeeewh88iwwe00ciis11htt1s1h-he-2vn23otuilaaadnlndslyse cc 795-7, have BOP's c]ose to that which would Be mate 7 IBOIODDEEGGRRAAGDAAFTTLIIOOOGNNROCTDRAAETTRAAITCAOOABNFLLENHSOOUN7NRSSFOOALLCVVTEEANNNTTT--SCCOONNTTAAIINN~INNGG FLUOROCHEMICAL SURFACTANTS prose) Product(a ) cc a80n11-n23 wn cc 802-23 cc m79s5-n7 ~mm29s29 cc m77i11-n27 me CC 7711-18 ~c 7m7a7-a3 1L3R 55006622 (0MC,L EE~rnuullassitfiieerr)) = c~ 0055--1I0O5S ((t~yrrooxnyy FFeoaatrheeer)) eTesstt Rreosmulatns BBO0D200 00..2288 agilg[gb)) p0~e022z00 90 <3800 aks mg/kg ~sOoDn2g0 N0i2l,000 m3) 7Lo-~hHGDrF.2,0tWvh8ae2ar,bc0rur0rg0ygenmgEiB/Cc~kODg=Rp7~To0Os%)NtoioofnfT.ThODDNH3(4) soonfgtvhe1 organic p~rtion. RHOtDa2g0 N=il0.1" 07 arte) B~OoDo2g0 == 00.,117079g5/0g()e) BO~20 = 0.17 g/g(f) E8O0D02200 99660000 mrga/ll BBO0D02z00 (<9E3M000 ~FgA/kSg s~Leeaftbeercreeenngcceeentoorr a62n60 0i38a444 1a2n3s1 4(8199)5 {79) 1187700 a419s7 4o95s1 5000622 e813e9 ((8a)) SSttrruuccttuurreess ffoorxtthheesseepprroofduuccttssaarree iinnTTaabbllee99.. t(S(h8be))e ~Thee BRO0D220 ooff cc~x 98901111--2233 iisn aapppprrooxxiimraetteellyy 9500~0 oof diechanatasive postion of this cherial. tthhee ttbheeoorr~ettliccaall oox~yyg~eenn ddeermen~d ooff ((c6)) diethanolamine portion of this chemial. eccco 77c9955--ot77f4ii3sh2aioa22s55%0antsaqgev~ee1osnuutsshesssoollauumtteiioo~4n3ootffhaa ddioifeetthEhAaaTnnool8laa0mm0ii2nnee ssaalltt.. TThhee fElluuocrcoocchheenmiiaall port~o~ of this salt is the same as that uf EAI 80021. @(d) TRFThonoilseOncTi~'FlKes3,Dis21altt2hsh5eoe attshheeuoomrreeesttiiccaa0lldeoopxxryyagoieeanntiddoeenmmaaonnfdd assumes no 0egradation of atahssessuupmmieinncggtnlnooosoocxxiiinddeaasttiioopnnorootffiontthhoeefnnitithtrerooggeenn the perfluorlnated port,on of the 0) mmoolepcul=e.tov ot co ((e) 8m0Do20 -= 2103%0 ootf 0COD ~f) 80D20 = 25% of COD 3aMwtA01000s685550099 aw _oao0ces 3M_MNO0000064 22557733..00004477 e e e ---- "- SSHETIAL eeST(xxdiopcpieeeEeitcachhtctaaeetnnddaoont!tffassrrm aooimwninnieettsyh)hheeiiCsarsoolovnnooaerrei:gg.eaannntiiFFycciluuopSpbooorsornroctctshieihoseeonnnmioicrcagalal nic surfactants with covalently bonded organic Portions gave nixed Tessith. Frose with portions gave mixed results. Those with SEyhecteertyn'acSyhasmmseaniaunea ocer"ga3n1i1c-p5o:rtihoenas,roipe03., quaternary ammonium organic portions, i.e., HMChCLiL,, s hydroxy foamer, and cc 7711-27, had no BOD. This ot smerpesied since sven nonivorinaced is not unexpected since even non1uo~inated GHheEkeLtnIary SaRsotnieus ssicer.tacTthaonstes aSuectafcrteaqnugesntlwyien quaternary ammonium surfactants a~e f~equently difficult to Bolyethylens polyethylene E heiieoR n a. and cc 777-3, biodeg~ade. Those surfactants with siyect components, Lie: ce T71I-18 glycol components, i.e., c9 7711-18 MisA indlertee s sog nt partitale Te had ~OD20 values egual to 10-20% o SPidptheooeagTrgerittriiasvirodcoanannCssttsOiiDoooBonnffo'sn.ooccffccisTt7SThgh7hiIsere1Te1a-nnHin1tooE8ednnrfeiclaaTaunnutotdgshecatslnicnrnvaastoot77meue77dls77ed--33oop~rbaegpss.raaiitnnnneiia iccxceceplecttthheeed ocFEffcbirrEseooaemnE7tr7T'vo1o7e1rrEd-ggR1daa8anBn,,yiOiscDc:adlibbiddSyys--ippgnolrrorratooenddaeuutbscceiittrSoossids..oeetgdqhrearanooOodtnrneeeewaocuaoaoaltttffdioaattnllbhhileeevsseaeeii,ssnnxpesttchehetaeend at sol$Sf8hbOri"asriecsi2dtrrcayvbayasata7ittoielVdnoiEoatEnynhNso.faanntedphdnieSdslcceirooSegananahtkttseteiiinnnuubiigiiinn.nnoccggrdreeeaagsa~tstriiann2d20g5gatacadittaaoyynsstthhweevwaisitt1dhh4se-ecdennoaonomy at TttT1ihe9hnase3edsts3sieecppaEete58driaTariottaionaaccdeaseosst,fuugcgoTggpumaeeslpiisaslnntttegeecatteuah`hisacencdtctgceli.giLlimroovaannatsggteseeedresriooobbrnriiggooeasddnnteeiiggssrrttmaahasedd.,asttimimoioinngghhtt RnlPoeaanrdEff]iuitooorrEiiminnooaarrtteaeec~scroeppmmoopirrletteaititoeonnsdouoeffrgfrapapcodotlaiatyvineeotttnshhyylioeefnnesthsgeliycvoe] LsiSaT~rudcrdEkfu22aaR99cc22ctt95taaifnnhhltttaaussessorsotwtlhchioeebhtneyhmhbi5iicccgsooahahvvleoeeasmsllteseesnnnuhtBtrBaiOlfolyyaDnc2ztn0ybao//ontCcubotOenousndDpd.coLo((prr77og7g%raa))onntiiscocosffs,, tthbhTuouottssee ScbLiotilonocnfwdt7iaie8aEsr0gaEm1rr1aat1dsett0asahhttitaseiiTdoounnTbibio$yetode3ssesa0tegt0rss1amoscdmeeraet"1cabwhoihaopnalrdniotiidtt((uiyym7c3o9t1hr)h.:.eaavvceeornA"ittSAbgateeioieeeernnnmooiupwnstmntgasas.ddeettthooewwiittLhhf CS cs2cht39ei320l9m8li0c1ssa1uualE -crwsitfaa0aicctDttii{ianvLnngiBets,,iaa6on3n0aDbl0ulu)ttyL,sali`sbssoaaarPrapppiEitlrnneoeosrsd,tTyuha:ceefftrrooCEmnoocmmomrntteethhrriaisccsiiinaoi$sllnt0gu0d)ythesarree5~ TahCsSPtahohhvelooeemusticoocibsdaoeaeBelneguissnsrnaagduDtTsaaeieittsvnniititgooesendnidoan--fnfoorrBBsLooaepttFbEhhhohioroFattEEitoAoAcoXdIssreeiygd88.rt00aa00Mds22o:an1ntteiiaaoonnnnddsovLILininnReeaa53qa66uu22e5e5oouuss pFET ps(Thrhhowooooolaattttuvvococteedoddilln eaeoeeeggngnsnrisgrtsataaeahdshdguasaastttita2>lilni33ooogo~5tnnn00naenaLnwsnmmatis))suasdrtitoao((eeibeb88rssfs00eipe,-rrdhc86svv1i1oiie]e5dteao~..dl..fndoolettN`iuoTsgaghhccnrteooesnnbsettsaiaoiiioutnnnrceseuaios hFBnsbaaoioevvnanneeda"seeideLSt~oieelezennininooannngJdfeosollnnuuuaeeroogirreaiionocnntnnesaa.sttsSeeuusdsrcfNtuapopabococrtrtptatabhinisnootottnsnssossa.~wwneiidogottrrrhhoafwdwhhaSceetsoonnlivv1oaainsllaeee~dnnsnssotttorSllurebyydbleieedes onto solid surfaces such as sand or silica gel. wniconssio 3MA10065510 1N020085 3M_MN00000065 22657733..00004488 --4-3- <N ee SNTIAy L Bloconcenteation c) NNEBoOliouobcbrloioooncccchooeannnncctiereacnnatt~tlrroaantstiiuoocnnfacsstttauunddtiisee.ss inhhaavvteehebbeeFeennnviddtooonnnemeenootnnal PmmLLfleaaaaulrlbboeefoorarroauarfcttoaahoortte rrossyyom..ceeitxxcaccanrrSSlceettatutustededueiireeppfassrvrceeef~riiiynn1avunoRsRotrsiiirckokooweeoicnricrtytaahhnthnasa(eev.v1ee5)ssE:ususnlhhlvtoofiowuroPonnnnenaacm ttttteiehheuaanotatatrnnaoddl- poPSBprcrceaeetttrvvaaifeennilnneeiuttoossrstsououoeelolcxxfrftccotorrananeenanattotctiiaeaeootcnneekissvttisehhss.rrrttyoorrluuooeggannshhsglglolywytstlhhteyerpporrnokoX(igtti7~olee5nny~i)ee.nnyyp:.rtbooPotuuenenrdidfnluwwohhbriiooccuh-hnd pmSP[(e~eeaavterppeerpfprr:rrliioouxasxot..lloroob9t9tec7hh7t.aa.t5taa3%n0c})otff,;aiiitvlletetbbeeluurrtytissstrthhetlteeahehssrrsosossuoummgragashlhbltllerdottnhhffebgerrylaaysccgmtitlaiioopioommrsnneeorrtouueorfilfiatvunseffrrbeeoeeund KaksfFiixeiiddcennnnemddeeseiiyyntnssgegt.:sso poebonenrRRteelsahshaeuecamaaomtsrrsritcctovehehserceeclssrrtyssanr[(csea71atta53t))de..sDD,oUurPpboOFbFennuaetdttnmaallbhhbeeyaoatvvhmeFreaaalctmnmessaaaddleceercaaantnssaniidmsiillaarc efrixaee3EtmcsEsaa5rlleeeSta4ennkdpdpeheplooeoohppnrnllllfaeeyylluoavavrpeepoprrpoeyyecaatsrsrallnooctowoowalltyybbeee,hhcCaallvveebeeaaurrtmmoobttrrohheeteehilrllrilmkkabbeelooeddmmiiaeeaalsnseedoof this material. ad) Eefrfreeccttss ZGBTdaaaa0bbttullaaeee`'eosnn~ EssEEANuauITmcmemmaaa38rrr00ii00oz2z21fee3ssaatnnettd4nhheemLLcoRcRururer5Srr66ee22tn5n3o.tt.xicesceEEtttAAoIIooff83fi00s00bbh22ii11ooaaanwvssdaassssaayy SCmadrubaeaecopfpthuhahatnrrndtoiaescaasdsEftta`AahhslaTcaingntgaoBuere0LL0RrsSogLcfr5S.oo66uw22tt5t5e..hhnEa~sbbOyOoyennrdeaspGpttpnphhtrereoooxsxxihooiecittmrhhaaeeNttortrIeeOllhSfhyaayiHnnsd~htat.,qwiaiucncaLLedetRRicaa55ss662255 mbbtTeu5eoocxuhiEcclcoeoaiinnanttsss,yyliddEees"AsurrcIcneeaaiddll8leee00tt2oo(T(1nss.iehhaeea'v3ve6eAA~.3bpsappSsSaeellwnndiioddgugihilhoxtdxtn b1ttIt)e)oho,eCmmloEeNEaAAdcILIseeOsrrSiaaH88rtt00eie00ae23qd1)uttaooatwwxxsiooiicuuccllii~dttyy ppBtrroaaaccfttieisihcc:,aalllwlyhyilnneoonnttLoo~xxii5cc625ttoowoffuiilsshdh abaenndeclssallsiisggihhfttilleyyd ttaoosxxiicc to algae. OEoEoFnnnnvviiooIzrttroohehnnceeesmrreennpssttruusarro)lffcaauccsscttcctaarranneetteennsiipponnrrggo.odduuttcLceetFtssssttss24((5hhTT6aaaa-vvbb1eelleeaaanll95d)s)s..oocebbeeIIeenn8nn0s5s-oorr1rmuu0eenn, SosSStefohchleeivvbteeufhEntnelitytsuuieooscrrpyFobyasccrsrthhotkeee~eimnmcissiiotcctsaacCe,lloo..nnttsesaa.uogiirkB.nnfil,~iaionnccaggttdLa~asnwwnataaty2sttes4ee5rrw6aa-errIaraeenneddtasnoordluliendissocoocpiipnnrnroo8ptp0aha5nne-eos1:0le, ptDolDrhrrioeotIddtbuluRutcectottyxslsittcooiaxCaxstsi~iycrcibissotiotolbytlyddso..letteroo.ve`SFfSdiiiitnsBnhhcwic.,eaeosastItidsEthhuaeeeyssiieesns tsSwosaceeosirslstvevuuheenmenneerctdduesnttohhhhanaaattvveetaahlvvlelieeserryy BootfEaxrhllseuieooaidrrnntoottooccaaxhnhgiceeocenmcniniiuitidcseysaattsliiolccbisanateeninfrgdttfveeeesnncocdotttte.sswx,,apttsehhrhheeioodevwussneeeoocvvlleeevvt,rreeo,,nnttatssnaah..rtreeeagoppSSnooyyissnnssseesiirr.bbgglliieess:.ttiicc EwBThaiseRcehdaSowlonouueTlodurm`TmalakeikeemrittteehhdeensSeauuxrprsfef!raaiccettnaacnnett,ss aaapnpptpeaeagaorrnisssoommr,eewuhhaett less toxic, is more likely. M3MATA01000B6S5S51111 _3MM_NMDNOO0000D0000S6S6 22557733..00004499 ee sce aes en " " iTTIIAALL" AGUNTIC DIOKSSAY DATATA0B8LELP8 5625 AWD EAT 80031 sen AOUATIC BIOASSAY DATA Spam, ON LP 5625 AND EAI 80021 Lab Retest Ftatrheesads ewe mma 32,29,38 766 202.o2r0R,e58e2~5n,c1e0 Bsns ww 96-H~. LOS0 a PA a 1429,2340,5625, (c) ot Bluegill s%6-eR~a. mLCss0 168 g569 . (d) ,3844 TDea~ptu~ntniiaa owwy 9~-~r. r~50 Ii 50 a-- 632 ess worry 48~'~". LC50 Law me we C~ oen sige G~ ~ cElhei 30-~y ~-~ Cell ~ght 161.9{a) 146 l~(b) 73 po o~nn~gase etCfelol c~iotus 95 o 43 wm (84,85) () SCCoollEoorr Lawnnd bbeehbaaviic1oe4rSaal-l,h~cchh~aa5no0guess cheered observed at at 1.0 1.0 3/1 ~/I while while agp egg-fry suRvivBLLLy survivabi/itT vas was (9)10deecfrefaescetd arotte1d.9xmig/nl. this stay at doses 4p50 ad inclu 100 1. ((b) (c) IEvisScmenTta aRbatYoryMme Tonilty Hrtabet on IL 40021 Lok S83, No effect note4 during this study at ~cses ~p to amd inclu4ing I00 m~/1. Environmental I~%boratory Aquatic Toxicity Workshe~t on EA~ 80021 Lot 583, FFaotthhenatd () 1MmL..innT7..oaw,EPlinsmatbaba~arc:eaawdyy,,8/ErE 22vn/i7zv7o.T ~emtnataL ll LLaabboorraattoorryy Matic Aquatic Todetty ~oxicity BaData Sheet Sheet en on TA EAI 0122 80021 ( (e) 5. T7,h Saban,SErirIormeTntal PEaboRratoey patie Lot 583, Bluegill sunfish, starte~ 5/23/78. M. T. E!nabarawy, Envirormental Laboratory Aquatic Toxdaity Toxicity Data Data Set Sheet an on EAL EAI GEL, 8002/, Lot 58~, Rainbow trout, starte~ 2/21/78. 2573.0050 austcosssi2 3MA10065512 Sun00087 3M_MN00000067 J asptme me aD Crs en waa J wma weamet ww: enn wm in mn re wma woe [Ep ------ T~L~ 9 FISH 9~-4'~. LC~ DATA. FOR FLU~|,~.J~ SURFA~ANTS Sata sire coyormaceron - corm -- codTyre mm co mons ww co wFeesntso?n aw am po rtp ase mr ps cn" ps emperor nan cri I. fosoccoieseos onn m common ts Sm -- snes w sn. --- ren som - 0 Ls tm cr ca 1 he tc soln, Th cre se This fluoro~hemlcsl was ?esYe~l va~er-bu~yl Callosol~-e?hans~ Se ~?h as a soluYl~s I00~ solids ~c 81~27~ m~tsrlsl (LR 801l-IO), Tr 2~2g) end as wa?er-l$opro~anol en~ The solvenY 8~14~s ?o have 8n ~ld hive caused ~e observe~ ~o~[ci~ ~)ff~ences. awsrosesers 3MA10065513 acooocss 3M_MN00000068 22557733..00005511 a6 "ee JENTIAL TOEOfhttllehhuuseeooerrrrooccetehhenneeavvnmtiiiisrrccooaannsllmmheeonnwSstteuuaadzrllffaateccehtaft~taaffnneettcctsstthsesaardrdseeaauttraafssahhocooowwtnnnnantiisnn TThaaabbvlleee 1100.. fssTTllolhiiuruettdmdstegagelleeleltyaooaettrfsetxsncnpooooensncchiicteomneenwmvndeteetdrddraCitaotaattittihoeoerannetssattcoothmmxhxueuiicaccchhiiswttuyaggyrsrrfteeattaeacootwtteaeaasrtrnccetttsriittvvhhaaaahttnntareevededattthhmooessenet snsyyossrttmeeamml..ly expected to reach a wastewter ~reatmen~ W5Khh1ii0lleemmmioonssutttesss,lluuddtggheee ttteoosxxtiiccwiiitttyyhtteeEssAtItss 6ww0ee0rr7ee1 srruhunnoveffdoorrno Tt5tiihhh-nneee1hh0iidbffbamililtitutoeniioruoorotdnnoceochesheees,evvnmeeiinnntccohaatewwllhhseetnmhwweaaosssweetxxpwpwccohoioosestnnuhtuttrhriieeennEruuAoeIeofsdffl8u0tffto0hooher2rer1ocssffhilsooeuuhuumddroeiggwceeehhardelsatt..oono DiTsSsholuugeuprrduffsgdlaaea,acc,ttttaaianoniItntd.cseso.e.S,shhhiaafvvnbbteyeoyst,aii3 snndbhdhhuoeeiitwllbbaiaiwyttydhieieundnedeggthooterggrorrroocctwwhhhfttrrelhhooiunnroioiorcrrcolcocehewcafefaufmfuasiseeciicccunnatttggeloonn ptEooopxxiiuccliiatttyyi,,ontthhsiihssiftsssee,eemmsshutuunnldlilukkeeelltyyo.. their low acute oODttnnahheeapannhnuuintntawuuwoossuutoaaohlrlraddneerrrreetssssouuollfofttfishmmvw.aaaasggsnniLitttathhuruaadgdtteeeccmmccdooirrf77eef77e11r11tte--oon11xx8c8iieccsiissttbooesmtoowrreeeen DDCDaaa2pppThhhBnnnaiii1aaa1-2aat3nnh,ddanAifitsYsohh 8f0itts0ooh2xx.1ii,cciittnLyyoarrvgweeeLrrReedi56fnn2foo3tte.ressneeceeenns wviibttehhtween cc 8011-23, EAI 80021, nor LR 5625. CWccwechhhiiecco77hhn77i11c1h1h-aa-ss12e88ffuuenniiscsddteesrrtthggheooeonnneeoonnDlla~Sypyeehssntfftiiillannuuggcorr(oo3tt7ccoo)hheeddnmaeeiLtntcceaeaarrllmmiiitsnnsseeuuarrcffIiutaatstccs.ettaanntt CSeceshfohhfofornfwwoeecenecceditdtncsscccchaheoortnrfnoiofnoenvvinciaactcssscceuxuttlplooooaanxxsr~iiuccDrpapeeleplsfafha,nfnfntteeisscac0.,tt.ss1(8ma7WaW)tthh/iillvlav,eeenedrryyLttoh~hieletdoosapwwp-prrahoocndduiutudcecstt, Sppc~irllto'aoanVnwnwcatttaezshssn.,.tfrfooaorutuIInttnidhdoynhhpaannodseoecttxopnntoootfysoolueerfbbfefefGeseer,ccovvttweetrr0hyoy.on1nottfgmgooegexrr/riismlmcco,iiynnbttaaeoottstoniivvtooaad.nnssa,,cpchuunllrriaaoodrroostt, gr0Zryi6oee8wga-trr3haa8,ss0ss6,;ornooahrrsyipcc.ooocrronntyaaltt gccrooonnwccteehnnttrorfaattiisooonnysbsearrnaasnn,ggiinngg ffrroomm 1000-1800 mg/l. 22557733..00005522 MmAto0es514 3MA10065514 3SMM__MMNN0O0Y0000000659 I sae - "TAL 8FF0il1sa1hn-1bb0li;oosassussnaaiyycssh ooannll cccccon881t166a--i22n77,,theLLRR sa22m992e299,, and and co cc a8Effff0oolla1uuuu1nnnoo-ddirr1eoo0iccii,chhnnaeenmncwcticiehcclaaca88llhn11t66a-s-sa23gulu77oclrtnfaiaaaccscnnot~cddnaaitnncacctticc,,ns8f8s0ste1u1uhc1eg1stgg-1ee1s0ss0oattnmmmeaatttyyhhheaatthhaatvvsoseeoxolilvcv3aeientntytss aBasoSnnfiEsg%sntL5tnhiRRhclfiesis22c99a2E2ofn95flltuuoossirraaasoommnoccpptphlhlareeeegonmopiinabbccinooaatsotllhtlh..icwiionnuAAelcctftduuhhfeteteecectpplrraffeeroiissinsseefhhnyntcchbDeeeliiofoaaaatnnssotddsshxaaeiyycgssirtyeosannt GGaddCuibiouefsxEfeieecnttcircooaeeenynasccnoneeofttssfaaggiooiaisnnnnioiicpstsrttaetoooriipxxeccaiinncctoiieelttffyyffleeowococtobtstubssslsedeorforovvrrceetlddhaddiriisiff((fffTTyeseairurbberellinfenfeaccceet93tss))haenwwiiteenng.rrreeeat toxicity of different lots of this surfactant. TGLTLeeoa-8s6s77tt877ii188nn6,0g7g27LLii,kRss ct3c2uh99ua32rrt95rc-7ee11nnm,,ttallyyya4 pppauurrrnnootddddieeuuarrcclwvttlaayyyssisi((mmnLiiisRRllvaae$#rrr884444ttt22ooh))ieoonn GqCsSTuuCcoeserotsskee8ttiea1iinnn6ogoii-nnnn2.g.g7a,,,t tAAtttsshhhheeeataannEtEmonnxavsvaiyiiddcrrddiooeaptnnnnaymmddreeuutnnmiontftaaalttlllotoyhtLitLhshaaaeebnbposorrwrrroaeaoodtrtsuuoottcrriittynynheeiasiifssteaarllssoo lefEFeouvuviorarasktptpihohonerertgraraattsittatintienegnsgsgttt.iihoonenffggfe twwottiixhhlleeillcisstdoodylleevvppeeeeonnnfnttdd..toohnnishThtteehpheeronndeerrueeeedcdsstuullffttaoossfrrteooffr this testing. sFPoiiisanhvenS9t66--hh=er..briLLcCCt5sl0oeyoonn11LL1RR 2929 2929 with with and and without without solvent - Priority III SwSSSaaiiiyynngccgeesiIennatcmmvooooassttaaqqSuuiEfaanllttiuuiiioocacrrrooeeccnnhhtvveeoiinmcriitoocchnnaaammllteenndssttouussnrr,,tffaac2oc2tn0t8a-a-nddnctaattsyys2D7Dff1aaii1pnpn-dhdh1nn8iittaahheeiirr ibss(tiii8e7omm)aii9,tsll3asaa7carra7yon3sdn0ctnooaTs1ne4ittd-mhhediooadalssyyeaerfmomdduruootlnlnoteetailitlggooheennanntoefeLCcrRdkaaottthn53ilee66oo23nn55omnajsaaaolnincrgdcdaallE7EAA7ITb1bi1io-o8Ss1a0O8ss0U2ssL1aayyss aErleoursercoocmhmeennidceadl fsourrfaalcltanotfs.the major TTfFooelxxpoiiruccaoiisrtteoyyncthettmee2sisttcmssaaljooonnrsurcttfhhooaomsscpeetoannooetrrnsggt.aasnniiossfmmsst,,hewwhhaiiqccuhhatic cbCBirorrloemoopommaarruuddeanneesciirrehttneyytppn,,eeirr2cssppappllmleeaaacncnjttttsossiiurvvreefaacannodcdoomtffpaoiinntnnttehvhvseneeetrrsttttteeooobbxxorrfiitaacchtteteephpsseoao,,tqteueananwqwttitiuiliilalcalatllicggiioovffvee a a bBnBfeeernlvccavuiaasiotuuerrossnooeetmnclmheyeettnnhmhtteeia..cvaammliiinnlTTiiaHhsmmbLiuaalEsrllefabbcddrhrtaaaooasppaanhhddtnnesesiihrrddowpptnoeaeannrrddsstthhppaeeeaatccllgtgtaaaiiqtllvvuoeeaxtttiieeciicsssistttynnddeeaaeetttddoaaeedd ptEirhaaeesnsseeenntooilrroyygtaaannsaiiavasyanmissldaatbccalaa.ennnnoohttaFsorbbeesheopxpwerrnmeepdcliitecch,taeeteddcctrroeaTxlil7ici1aisbtb1yll8yytoffirrsoomm pCphRforriiimaagshpcchaattllryiibeccidaaot"llaoSllwsxoyyisixtachynnoo0tn0odnLatRttoodSaxxaa3.ipip6ch2hc5nniittFddoooisasr,,fimiesosxa"hahrannedmapPbltuuEEettoAA,IxLimmcooC88ddc00ee00t2rr2e71a1a7ttf1eewiw1llhsh-yyhee1nn8buttitoso fort tons to compared with less toxic to aLallRggaa5se6s.25 is more toxic to fish but T2CScsohohh2leleeuusvmmaeeeiinencctstaatesll.esssutii1sTn7tt1oowwshh"aahBiovveicuoochlii"ddddottnbssheheeyeyyynn`oeednrroaalnrggtyeeeiissotcnossiinooclclpddrt.:hoesefdffutecanCCctcehhtastrrstsoovnniiifffctcrrlhooummoDBraaLoppi-hsnnen~iaa SonsvTntaeaasulsleduretteissetsooffl1oe0wssirtt:slgoolxxaiittnccbhhiieaiastnnteyydoi1n00iie00nn mmop3gne//leAlylimoooirnrnhawpchriyioccdhhuccotsstshheoowwwibtaaihoddaeesLlslCaaasyy0yseedd preliminary acute bioassays on this organism. Suatosssts 3MA10065515 _MN0D000CT0 3M_MN00000(~70 22557733..00005533 I SE a-50- 51 sepestatton 2 og b) siosegtasntion = cc 771-3 me cc Ls haut Biodegradation - cc 777-3 end cc 7711-18 hav~ ed Hot Thaten both given indications of partial biodegradation DD mri pnd Hoy in a 20-day BOD test, suggesting possible ELE degradation of the Carbowax portion of these a molecules. Studies on cc 777-3 under more an rigorous conditions are recommended to EE etI Triet s thnetons substantiate these part~al degradation findings SEHR aL and to identify degradation products. I. The recommended test approach involves using Thm rs re PY preacclimated mlcroorgan~sms as inocula for a Dl SRR 28-day BOD |92). If biodegradation tests are AR tn positive, an attempt will be made t identify mle he gle Lo ls major degradation products. This testing is Btn caa) ~mportan~ to substantiate the previous Pi ee ane, inconclusive findings of partial microblal Be EE tenssy degradation Of 3M fluorochemlcals with covalently Foi ik rp bonded nonfluorlnated moieties and to determine Sprint ER LAS BE if perfluorooctane sulfonlc acid (the EAI 80021 Heme Ra ne fluorochemical).is the major degradation product. eR Analytical methods could involve techniques such SSIS SH nel sr ae? as methylation and capillary GC or TLC of radiofrist fils labeled cc 777-3 degradation products. The ee TL LSE lon ot label should be on the perfluorinated portion of We the cc 777-3 molecule. 25a 302 28-Day BOD: HI priori cc 777-3 - Priority I Smeramatnisieon Seonial Seemstetoation = Degradation Product Identification - Priority II mr No degradation has been observed in BOD tests on Sng a ae pte ig the hydroxy foamer, cc 805-iOS, or on any other She quaternary ammonium fluorochemical surfactant. Hn ep ek Since the hydroxy foamer is an important rer per foeTe ine component of "LIGHT WATER" products and is also HE SH Bo pe finding a significant use in copper mining, ere LTE Te rigorous biodegradation tests such as the SCAS* i hy ra. test or soil respirometric tests are recommended. Preheat hyde This testing would be greatly facilitated by the aE ES use of radiolabele4 hydroxy foamer with the SE AR in radiocarbon tag placed on the hydrocarbon portion Eliot of the molecule. J If results indicate significant degradation, an Foon rimriin attempt will be made to identify degradation Fug products. PT Soil ~espirometry or SCAS: Morn Hydroxy foamer - Priority ZI SEEt ten - Dearadation product identification - Priority III onsets snttosned stutsn *Semiontinuous activated sludge susrcossre 3MA10065516 pp 3M_MN00000071 22557733..00005544 asin : AL WWSEshhiuuiiogglldggeeeeesssrttttsashhdeesttthhssieettoyyrrnuu:wcwcititlulutllrreeeshhtaaioovfvnfeegEeAAetxIIxottrdr68eea00mmt00ee22e11rrieeasanssnddioisnstltLLaayRRnncc55ee662255ttoo dGSbSsene ious'otfgcsdtfraceiiadugdcdanriiattaeetdiinniosocttntlnliyeyonccnvaarr,iniincnggnaoootontrretsooseuubbtnsseeitn.gdfdtooeepptMeseOsonhnhroddodsweweadtdetFthhiuueappgittosoonnroottnuhthtolsoeeylisrrooeccrccouubrriciinn bbSanlulobodsadteaqaggunrtataatiddicsaattteieioonnntvhirettoeensssmittpsseencaattrr, eeedmrrceeooccremoopmmlmmrieeegtnnoeddreeodrduessttioosatffeauurnrorcttbehhiceerorf iCsECAouAoTInbTn0ds'a'it8{85t0at0ei0ni0o2ot2n11nimssaetaadenntrddiigFgtoooLhLcerrnRhoouue35ssxa66il2p25y5y5ecmitffttxeaoaoidvvnoobbgrrii.ciiooonnddmhggeepegglrrebbaat~lpddeoroaadodttesreiigsesoocrsenntaia:.sdsdatatatwiniioctonhen of GiCwgshiaallelrruemldddsieegecnenbaelsstSsoohua.iiastlltedhSahanaunusdssdcuhchcbScooeesmmeetappnnsuoodssimaatteiccsxccillffnciiuugommrruaatttlthhtedeeehdrdrebeitiptnonrooooeccdxttuuuhthlceleesatsanetsetdeeedddwiwwtuihiptthhto ppEcIeehn'ryeryemieierioaoaicdrdcaaiillcc~Sssaaee..llpplleeyynn"dcSAppiiunrrncniiihgglmsyeeosotddnntiucvwdarrliiieettesshhsmuulletttcffsshorr,,ueoeslsdhdhsaanndddvbdeeielccowlaaoeuyyuxiiltisnndenggnvdobbeelevde up to SeBmteeeallestaeeseetcct,rittiinrrnagogoolrddseeff.,,soorreammreeAffcaanllhssauuiuluoonryrrrgetieimidndeeceefnanotlrrtreeolloomtffeeehaategsh11rseo44dC0sOUGu32ss,,iigwnnrigglaaaldbbasstttohohiierernobbvneeofeddlllvpuuerooiiornrndiiuddceets oSboufafssecrE,raiadadoitirooolrgaasrbseaeeaplirneacy~dh.inffglluuofoorrrooccohhteehmnieicrcaalidssegrbbayydaTTtLLiCCon products autoradiography. RRiiggoorrEEIooARAuIusIsse08200((s0ss32oo11iillp))+-riaaPPoeerrrrriiiooootbbrryiiiiccttyy1b1bii1oo1ddeeggrraa~daattiioonn:: LR 5525 - Priority IX 2RBlT5iioo'ggnn3ooggrr-roorttuueeessprrrmneaasnn((eaaiinee.otrere.aoo,,tbbiiivcwcveeeeebbkkiipasooe--ddrmmeefo~gginnrruttaashhddtesaai))ttniiaootbbnneuudrriittaaSeellussttrssfooffaciiLtLnnRaRvvnootll55vv66i2i2in5n5ngg iaawsatteeariri-rssehsapitruuerrsaeaettnteethd~atoisslvooeiilllpeaalrrreefel~aaolirssRiooenarrSteeeccdooommmsseeuannrddfeeaeddck.:tanetnein Analytical methods will be the same as for the rigorous aerobic tests. RRiiggoorrTooRuussS6aa2nnaaeerroohbbeiiiccorbbiilyooddeeTggHrraaddaattiioonn:: LR 5625 - Priority III ydPPeehhtgoorttaoobddseaeeeSentg~grerirgaa6adtiddnaonaanttoooiinftoossnntara-3=3tMeSSdiiffnnllccuuieenoorrnaonooqcocuhheepepomhnhuioiosctctaaoollccshhoeelssnmuuuiitrrcciffaaoaallncctt1aa1nntt7)hhaa.ss ySiSeseu0uxptcggplh0gloeeobrrsreaatta~steentoddosrridyylettiomocoppanhhttsooeettstrstroeoaadantecpdpegsoodrsrsoasarsiddiib~abn"lttiseieiaeooqnnnuaasecciottts~uiiittsvvzuuaiaddtntilsigeieoososlnnuatgaairrebbeeyoynnts{ss-7uu1rr,ffl7aai2cck)eee,ss sthuheechoorraggsaannsiiicclicccaoomnppsooannneednnttossr oo"ffsennnaasttioutrriaazllingvwaatraeegrre..nts" like CCEsraaiaacldnnliidgoociittadsaaaagsttggaeeeeelddf,.li1nsuwwdooiirrllooallcclhhseeobbnemeiidccibbaasoollstthholssvccuueoorrssaffttaaeecciddttnaannoovttnanssttt,,oeorLpspaarrcnneeoddffneetoorraFraaibbnlliyyng qsasSHqeieouunlnbeesiseocioiauttssiBizygtiessinlaaSngmmgppa'nllansegedeessnniagctwnwltesiis..lloFllordBBittooshh3ttsee1hhnon7l,vbbtteeehhdeeaniLdccreioonrras1aattwds2eeaii-ddtaaoettnreesscddiinllciioiiccpnnnaaetraVUiiyayacnnnca4doiosrnr.g AASPatfnfrnuteatobleleedsyyrruazceetbiTddsyrrreabhsffydodourirlnTaaltitiiiiicgnnoohiinnttta,,iiuaatflloottrrhhaeeffdll3i,iussoooaagrrmm6r,popoalclcpeeaaahssrrn,dbhoowwnniio1llr2lla-annmGddobLb/jenecootrrhesfxxo~dpttlaerarlrauveoicgcgwoththidetetnsddeeg.,.rr mpEleeriotohhdoyyuilHcaattatsiioontbn,yh,iTeLa"taCnnidaaaeuff?toorroraffdlliuuooogrrriiaddpeeh,rFeelloereaassGeeLCvuasfiionnlgglowtthineeng fluori~e electrode. 3mMrtA010006655851177 Sn MN030000T2 3M_MNO0000072 22557733..00005555 ee neo TABLE IO omen onvimomeTaL erricrs arate) OTH~ ~NV|RONM~NTAL EFFECTS DATA(8) on Fsosoentuicns SATACTINTS ON FLUOROCH[MICAL SURFACTANTS Sum = Tay sroser 80021 802-23 7957 Boa-t0( ) ~ 816-27 cc 8011o10 cc 7711-27 7711-18 Cana 250 mg/I None Bf 4000 mg/I(b) Non* et 100 mg/! No~o aT 230 mg/I None sT 130 mg/I N~ne e~ 300 mg/I None at 500 mg/l Bomis'eiies Frise 15 m9/t satin: 6260S I.~ mg/I I.O mg/l NO inhibition Of NO Inhibition of No tfflct on Soybean, rye. and (79) 5428 489~ 49~0S 7009 2174 600~ 2174 4197 (871 ~77-3 Nonl aT 1000 mg/I of broods, and brood size in LR ~062(s) ~0~ InhibiTion ot None 8$ I00 eg/I 1000 mg/l 5062 (~) [xD0Sur8 t~ ~kl exposures Jh 80021 ontl.uid fo~ 4 hrs. es oppose0 to P ~o 10 min. sludge (C) H~rO~y foSmo~. 1966. (~) MCL emuiS|tler. amarooesste 3MA10065518 3aMW__AMNNO0O0T00000007733 22557733..00005566 i-482. pesomented Testing nTAmL Recommended Testin~ 22 Poysicat coanicat a) Physical Chemical Solobiltey - ater solubility daa on Sn Solubilit~ - Water solubility data on 3M Je ee une in cefsslttuiionmraaoctciihnneggmicttahhlee eesnnuvvriifrraoocnntmmaeennntttssa!lismpooabbdiiellqiiuctayyteoofffortthheeussseee in a et ites Shisbtitty segeuresents compounds. Further water solubility measurements Cen ian ard Tot on 2~ fluoroehemlcal surfactants are not Tree erie Set sre ses be specifically recommended, but some may ~e prostheticfh J included as part of efforts to develop structure a da activity relationships for fluorochemicals. Pacsision costtictenss - octanalwater pustition Part~tlon Coefficients - Octanol/water partition Ce eagomtentiel coefficient measurements on fluorochemical STELLGTIS ENE Sana ana in Sass are surfactants EAI 80021 and LR 5625 are frei Met de Eeene can {ecommended. True "partition coefficients" can't Fp Me Rog oy be made on these ionic materials, but reee Shut ee don ToetEiciants can be octanol/water distribution coefficients can be A measured. The usefulness of such distr~butlon rr To evihatiee Shemctypais coefficients in predicting chemodynamic Erie heer tose tees mactition properties from octanol/water partition Ee TE Stn Pt, coefficients is now uncertain, but these onerements whai he ReipEel in Sacer ining hese measurements will be helpful in determining their HI AL e REh T util~ty in this area. EAI 80021 and LR 5625 are Ln trio HEE tnd LL 2a appropriate choices for this testing since they EE a Taree 2 ehietotaasina: serfacon represent the range of fluoroohemical surfactant CORI a halt Lone ar ane ater solubility; EAI 80021 is one of the least EL suttietanss, arabs fo fave one of soluble FC surfactants, and likely to hawe one of Fret rEA the highest octano]/water distribution Ee Eecrentcats. coefficients among this class of fluorochemica/s, RE Tene Se HE nent while LR 5625 has one cf the highest shine solubilities. igtrivueion conteitanss wii be sessed, 1s Sooroves by the Oech (BT andthe USERA (89) Distribution coefficients will be measured, if possible, by standard procedures such as those approved by the OECD (88} and the USEPA (89). Erp HE Key Ry The separated phases will be analyzed for total rE Enna She Huetierenton: organic fluorine, for the specific fluorochemical Stata ie elloving Bethpincion: or bp by capillary GLC following methylation, or by EE Se TT RA Chote using radiolabeled materials. Standard samples Fr prepared in water-saturated octanol and EE res TER RT contrat. octanol-saturated wa~er will be used as controls. hese gistrinution costeisions messurenenss azo These distrfbutlon coefficient measurements are Te STERN given the following priority: eax 30031 - priority 1 EAI 80021 - Priority a any LR 5625 - Priority I suntosssis 3MA10065519 S074 3M_MN00000(~74 2573.0057 i. - toa TITAL SSFS5o6eEei2l2cSll5o4mTTaaneLnndcCddo--EaASTtIselpinen08cac00tee0i22n11ppg.rrgseeaalltvviiheemmesiienanaamamrbrbSyliyasgsuutssaoooo:uullssll TTTrrhLLeeeCsCsuullsttttetessssa,,ttnssdwveeeoornn LLRh TTUnGrhhS3eeeeEEcPPoAFpnpmrrrmoooessscconouieeidcl1ddeuursrrTTeeeLLpCaEeacrppteserrigtqonouaucgcinieerrdddeeatususrhrrdeeesaaeTLwy1JCii4AtllCCellh-s-ytllsabba.veebnaeelllffueeTooeddhllellootsswwhuuseeabbtddtssattndrr((aaaI7rttL1de)e).. ahchnhaedarraipacrcieotederursicyizeazesteassnastt.shhteeamnmdooabbriidlliitTtyLyC ooffRf ttvhhaeeluffelluuaotrrhoaotcchheemmiiccaall in soll systems. GSSioovl~elln'TTLLtCChetteefssottliilnnoggvinoogff pffelliuuooorrrioocccyhh.eenmiiccaall ssuurrffaaccttasnnttss iiss given the following priority. IEEAARTI 56882005002211+ -p-ePiproririoioreriyiteyyFT11 LR 5625 - Priority II SpebB8reiieoeocnbnaaFaddsbsfoloo5rryuppn3ttdhiia0oottnno ~-btbiihAAnnessddy wLtLtoRoRoulpp55drr66oo22at5t5ieesiiaaennnnddbi~ninEEnA~!dTcraattt88ese00,,0022t11hiLetthhaassvveeeeeemmss RpmrSFiireeiccoccnrrboogooammbbmbeiieltnaanyhd)ldeeetsdaphparrvtototihtthraaeetottiihnnnessyBsBelinowoiitaoannauddllaasadooccrrttLppiiaattvvlbliaasroottoanenetdsobSrSitnytssduulldduspiiddrteggecoeesst..otbbcheeeolIIttrruu(ns1iis4s) wBnabueneodsdui"lnuuFd~rssaeaedffd`tiBuuiheclloermlaoaEiitsbnnnetevllddieeeeirdsttioekenmmerrmaalmmettyniieetnnrraiitiilnnoaeggllpLssawwe..shhbseerttathSShthueuoercrcrrohhyuttgssphhhtteerususodedaetiioeevcccsseooolsmmtpwwpeoooo(uvuuu7nalln4ddt}ddsesr sSwstFlottrruurreedlooaagdnntteggms.lleabyyennttemanonssddsyytssbttbeeeelnmiddkiieiisslnnppyoottsshtheeeoeddipaoqaOqffsuusceooWwuuiitststhhhroppuaahhgccaahttssiieevvaaaoottrfweeaddsbbitinenddwster sludge. BSBiulrootssaoocrrtppattniicoosnn tteessttiinngg ooff Elluucorroocchheenmiiccaall surfactants. ALLRRz S566822055021-- P-PrriipoorrriiiottryyityI1I1Ix1 EAI 80021 - Priority III VRVaaep~CooerrraPaPrrreyesssstuuorreesst--inVVaaatppeoorrthpperreessvssouulrraeetimlseeiaazssauutrrieeosmneennottfss aarree FppnflerreluteecuooddeoruiirsorccoscettcahniihreaooeynnnnmitsistcscoaaoolwlffessisletelaaninnnvmvaabdiietrreootsmononammtgremehenaanetkktaeeafvllooqqlluuidSaaaoiitnngssittittliinrr~ttigizbaabauutttsttiiitiivvaoooeennnnd..aorfd PpSM~prrSertooEaoePspbbnAueaarrbbetll((miyy59ee80n)~sbbteesosopprreeewsrricOGfflaEEoolrCCrrcDDmmhbeeepp~darrtoomabcc~~xyeeye4dbAuAu.nnrrfaaeeollsslyyltto((iiw93cci11aan))llg aananasnddntddanwwdiiallrlldmmoosstt Properties Research st CRL. EEEAAsLI68830050022117S -p- ePlporrriiiooerryiittyy111I1Ii1 L~ 5625 - Priority II SGSGstririneneRccaaeeettpeehrrttehlrpipsesrriiootSmrrhaaiirttttoeeyyutrgiihaaiidlss iSggwtsiiiTlvvLleeunnseRt'tytIioopCniScwwoaoPTrrIlTkkPl,Eyoonnn"eenantnLLtReiuerra55c66ttt22hhu55eere. aTIttUmToiSsSpThaIelErsSeo 3ta hhhrioiuggghhheerr ivtvsoolluuummseee product. in PTFE manufacture. product. 3MMATA010008655552200 3aMW__MNOND0O00O0O0C0T7S5 22557733..00005588 _s- 3M LR 55662255 aanndd EEAAII 8800002211PPhhoottooddeeggrraaddaattiioonn:: pi pp On silica - Priority III Jubii is HN Sensitized - Priority Ill syacony tommert photadegeadation: Hydroxy foamer" photodegradation: tiga ah tris 8ensitlzed - Priority III Btoconcanteaston c] Bioconcentra~lon Seaggan an active sede of Soneumtrati ppBeeercrfatulisuveoorroaoonscctatacantnoiiivcce maacociiddde e~oxxfiisscttossnceiinnntrraaatttssin1a{7735)),, iitt rie hg EA seems possible t~at fish or other organisms could Tey onsantrate this or obec Flmtocentost actively concentrate this or other fluorochemical roe the snalomenrs" torecor s~rfactants from the environment. Laboratory eles mrauid he Bene vo prove or Giesrove this studies should be done to prove or disprove this Sosaishitey: `mote' Seay elon bicconcepiistion possibility. Whole body fish bioconcentration Toe ies EiRiaspeed techataues (131 ang studies using EPA-a~proved techniques (93) and Sinaia te radiolabe]ed materials are recommended. Fish blossncantzation studies on Eluscoshenisal Fish bioconcentration studies on fluorochemical surfactants. Serluoraoctansate (ix 5635) = Priseisy Perfluorooctanoate (LR 5625) - Priority I RertliersnianaLa Perfluoroctane sulfonic acid (EAI 80021) Fai Priority I d) aB AaEHqqqfiuuuftaaaetscttotiiiscctcnbI tbeioinoxolaiaescsaissatayyyEsspErsaorrfeeRilpperrEsooppoooofFsseeHddsSaeevltteoovtrasaclboormiasppcelillevkaetctceeeteretcsdhhwee d SRN ret neil fluorochemical surfactants. These bioassays employ standard Environmental Laboratory will pEEE StnrhnEevoviciWrezhodoyEs nnudmmrrReeeonnsxttyisa(t]lfa8o7enssa,noc9merr4e,see,r9se5nn$ih)ii3nr.nn5gg3otwaoittneessmesitit3ssx$tt5auh3htr0aaee0vvss,ee-, bbesAceecasnnsu7Tnd9d9io6o0n-nn1e3gs3 oomSannnh0da tacSFEhlcEEleSSE8E0FoECff5o-r1sttn0ohhleFeia(edCtLnsRoo,nxaNtiaiocotshito.etimtyyiah4ny9ootfd5fes0rncttxTaohhyfneeodssneefASok5ams79lami2t0ex5i)srth.url5rheoseas.ssAsCsoaiTursomi9Troi6amdln-ruuihgtegsrs.ttboonhnat fone rnin LC50 for Fathead minnow the surfactant alone to of 20-25 mg/l. Tests confirm this toxicity on HFlana= 36eAns.G1250 level are desiraDle. Fish - 96-hr. LC50 on on Soiventtras Solvent-free Mygroxy Hydroxy Foamer - Priority III + SPrTsheauRoccotoirTomaodmmteeeengngdrtceaaadddtaatotoininollonyynet11ifes1ss1t1ie %sst aodGnnooeesshhyyntdnkoroortosxyybbiiofofaodoeesapgmmrrmeaaerddeeaarree under rigorous conditions. Swaroosss2t 3MA10065521 Sus 3M_MNO0000076 22557733..00005599 se FT. TIOIIEINNTTIIAAYL HJ0sotylARliggmeaeeeSBliooaspssisseaeyyssroosnp tgtiihnee nneesaet fluorochemicals contained in 202s LE 2929 BEM 805-J0 Ema cc 773-58 HPSesPrerietioooariyrriitstteyyy Hii11 Priority F2288--a0D1acy7cmDD7aa7pp7hhp-nn3riiaanBBdiiooeaasrsssnaayy oonn tthhee neat Eluoro- Priority neat fluoro- chemicals contained In ia a36n2s LR 2929 S2E8R, cc 805-10 PseHpreiorioorntniityyyy i1fx oIfI pes cc 773-58 cc 777-3 rer Priority II Priority II Priority II 22557733..00006600 nioosssz2 3MA10065522 au wnootaeer7 3M_MNO0000077 ES IAL D. PP1.hhoosspBphahacatkteaesrsouns 1. TATB 7Thh9ateeic5lk-@ a2E E)n3nrv,ovirueirrw Renroodhinnpieam cmrhetaengenteLntacsailslooonrnTLLeeiaantbberEooo:irfrcaaattth3oo`Te5rrtyyhhIUhhiegaaaahsssaeggmTsteoetinmnxvesoeorortrladsauatohtmeemndedeseocddneppasarrotaosteatdssmuuuieeoocnrtnntsgscocfec P ERR edEroeE eaconal 1J8 JA044-R4 BokHaEkastcohntaining in the FC product line. It is a mixture containing mostly the ammonium salt of the di-phosphete ester of the ethyl FOSE a/cohol, LB 3844-4 but also containing REsome of the -- mono- and tri-phosphate ester salts. a) hA~TIPhhrehyenyysssiilEEicenncasvvialiiil-orzrccooPhnnnriemesomenepeininectctrhaanatll]liiesdLdLyaoaattbb.aahhaaoosnns ggteehenneerrEaalttueesddtosnmoonentcal the fluorochemical 5) Dceosmrpaocnaetnitonof cc 795-23. b) HfB cSI Dcyryedcdgror7robo9alal5dtyu-a aisa2toi3tRionssen(-=3N%B2TT1hh4T43ee6a52t6arss9eedss1uu6pD.7llr3ttosst223240,ooifhfnac2aru4a0au))tnehhsyys"edTdmh:hrreoooowtullhpyyehhtsshaiia3ttsst;h ssttuadyy on on 6S,hed3.ce Scu1SiE0on,r,nrccrceueaeab1a2ncand,tttteireoaadiarntnai4tcceohhoatneatn1mn2nii.sa43cctb5aaooellvvCdeeidppfroretcrehenhcacacotttuu2rr4rssu1iioohNnnroriScu1tErrooiIesffaRaalEslceSacgyctfyptepphH37aerHe95tes5-est-L33,e2aR03nns:.tth36a,8ta4aks4T"9P-,hr4iiaisnns LS ila I denleaL l FytneTlieRts SsehsoonSenR:ST work is significant because it suggests that rapid chemical hydrolysis of cc 795-23 o L~ 9sI 37[,839i~545oo54-sd7-2ee4~rgcraoi~agsnndatvataoutilinovol(enni3dk6.e--boloyBsCethiihocidna1bbe3sli4gtso0ohrr6aecaa)nhddeeaeanmtntaniiviidccioo.narnnslointntmooeceexssoxnyttrytgiice.enninnggosSdiooeeonnmmeaeccnnccsddnake Sif(tlBvoaOsDdi)ky paretests tests (96, from ARH CO LR #3488) and inconclusive shame the Fate of Fluorochemicals hSSTtT1h2hthaeeeuesdsyBc8StiOc0,aD0aPaD7artc9iteo5tcsn-eet2th~Tr3.errH iRefeeslsctuuunEllodttrE sosoec"hllieeeSnmaaheAdidecSaSthtlohoredrathtctyhhonceemapBSiococnoboenonovncocytflloruuessicniisee,oonn7nsto9et5ttv-hhe2aa,i3t oSCeiE{EfsaLE"aRsnoitcmhnl3hTie8lyeSa4aye4leobl)ariraS.ygobgadoaneBunigtaSSicrpiicasrnhnrd,ecacedeledefss.thhi(ooosSuufoaoklTpepdhr.treohtopehhhnaiaa2anevvc0noeeh-oldevt,abbmayseeiewecwernhahnBiliOccPnvnhhoaeerxaoabmyfryraalglkkyeytceencessed7teu9oampp5,a-n249d30i0%f completely degraded in this Progr fain any, degradation could have pLretainit l h EL remaining 60%, which is the RSeeg ] i test, very little, occurred to the f!uorochemical if TTS SciihhonneemcepooponsseI nhchcealdainkukitesei.ioScvfellaanssbatA kkeibcybabbiuiieisooL yee@daeelEgngvGoreaaac~daaInanactatnilinvoyoRintngiuicsesa,ttluu(lddhiitceee)slschaanarxiIzeeqoueatfaor cc 795-23 was available at the t~me. A nonapecific analytical technique (TOC] also did TEESE Bicaure mecarial precipstaces fron not work because material prec~pltated from J get ate solution, possibly due to calcium in the culture medium. sustoosss2s 3MA10065523 uses 3M_MN00000078 22557733..00006611 J se oes "HTTIAALL TiTeEEhhnfieevfmiercaaaeotvvansaaminielltnaatbaballeale smdedeaafahtttffaaeeccrttddaseeeammtooopnntrssoeottpapreresararittttceieiieoessytthhoorrSfefoeeecscecava77r99t55-e-2233:: SopsZor)rtpogamaiaeentiliEneaashsgma:))ss rethant mt>SL(Tli393ns666l0tS-n0m0ehoanrr.lsmaaoTg/pa/EaLaela1Ccr)tESua0tets((iF91Co6at9E,ntonhxieaaiLitRacodiuta1Cny2a mlns0ioe4intt:,hsnoonwLaLn~nqEau{rS~aPa1tic9i(m1c9eS,6ap)hi]LasTRlees n SSIL HE here tte che Slogeorambinics of 2256); 2) it does not significantly affect waste treatment system operation at <2200 mg/l (96), and 3) it does not tatar@ the biodegradability of 2. Recotmreenasteesd Tceasrcdibonard 0Recomsmyesnidceadl Tepsrtoipnegrties a) TnTePEoonehvyiTiseerrinnocoaanTanbbnlmllaeee:nnPttrttaaohhlleepteorrmefetooevvibblaaiietllilsluuiioaastrttyyii,,oocnnommreeootsaffisssuuoccrocceenrm77eae99:nn55tt--22sa33ooiffl.wvasatotreeprrtion, 9ssfIhool1ieluoluobebrciRoTlLcoECihea.,tenym,iiaiecnnoaddpnlatrvatcaSpipohtomorirpsoooosnpntpreeraennecstttsosseaeeu*sgfirefteeiaaircreoiooe:neffnrrtccaee,cdrccaooms73mmmo99eoei55nnnl-.gdt22ee35sddo..rptiOOoffn, tiehmepsoera,tanstt oluesbieincleT eitytThuaeanydicchapnanarpmmtoiamtssitteonnaeaattsariielliyyLm?obbseet uusseedd to to fHWpaartrteeedrrictSSoololutuT bhbieilrliictycyhem-- oTTdhhyeeng amEElnncvviirrpoornnomspeeenrntttiaaTellRs.LLaabboorraaattsooirrdyy wuuissliilnnggmeccauusrrurrreeenntt fluorochemical solubility rreeccoommmmeennddeedd mmeetthhooddoollooggyy in water ((998)).. SRE he HE Ci Analysis of the saturated water samples could SAeritaolreientaatEitonScofietheeetrehlybitaitvees. ssoolmomAeLsi;itsaltSFeritnhge involve GLC of the methylated samples, allowing determination of the relative solubility of the ee ane aT mono- and @i- esters. Alternatively, or for SCornminaeputrerss. febicioied' ic Atha confirmation purposes, red~olabeled cc 795-23 couldVatbeerusSeodl.ubility of ce 795-23 = Pricrity 1 TOe mOocc~ttySaaunenWroaoeltlI@e/os rWaaatbttySeeporrrlsotucabPseniaor ddlrruaittrrtiiedyttsi,iooopnwfnrioCicCCco1ecoosdestuftb7urft9E"eii5iscc-tE(ii2h%3esei@ant,tt-se8y9nP=-sg)r..iKKaooosrwu'ifTowthvtniyeihtllolslIe bbeo e sieiEe Hr Seriating analytical procedures will be described above for measuring S73 ater the same as those cc 795-23 water Daismtriybution sOlubility. Distribution Cooteicient Coefficient of of ce cc 708-23 795-23 = - Priority I +C*= l"fulEsuroorRsohcheTemmiiccaaIllL SccoomRmppoonnIeennttss"" TrreeffeeHrrss Rttoo ttnhhee emmoonnaoo-=,. dis. di-, 3nd and tri-phosphate ester salts of ethyl rOSE alcohol. Eo -- 3MA10065524 e000 3M_MN00000079 22557733..00006622 e --e ---------------------- -"57=- To Ea Soll foraunic aster agsorgtion costtictent toc) Soil/Organic Matter Adsorption Coefficient (Koc~ ~oil sorption measurements are p~oposed to Latins he mobiles of Sr 7050E3 tn the' sail evaluating the mobility o~ cc 795-23 in tee soil ee eo trapiar Shere data will sid In environment. For example, these data will FFreEsiEcTtin inse oancaetaandssseTanhtisobeorLkevHchiiTnaeeFioinow standard procesures 138.59.1003 "Ene ana1yeical predicting the rate and extent of leachin9 from landfills to groundwater. This work will follow standard procedures (98,99oI00). The analytical EEAIEOTITTN sane an used cor ater methods will be the same as used for water oeElity and rene Dor besaues of rossivie solubility and Kow, but because of possible IoLSRHLLIEreonc Oly thet, of geil) interferences caused by soil, the need TE radiolabeled material is greater. Roc of cc 195-23 = priority 111 Koc of CC 795-23 - Priority III So ic - This procedure vill confim foe Soil TLC - This procedure well confirm Koc eT Eoamandns pr scadstds vill measurements. USEPA recommended procedures will oT Se BTioves. (Hs Frese. S18 Brocesemen agai8 be followed (71). These EPA procedures et hatte meeriats. require radiolabeled materials. sold Tic of ce 3-23 = priority 1X Soll TLC of cc 795-23 - Priorlty III Yargr Povspure = Vanes pressure sessucepens for ~apqr Pressure - Vapor pressure measurement for EE Ee Tt Shaint cc 795-23 is proposed to complete its physical inn og Cl Rr property profile. This measurement is necessary Ee cee mae ot 14 ovement to estimate the extent and rate of its movement Bes SOL Ta sf into the atmosphere ~I01). Analytical and ELperties Robart at cai 14 Shobebis the post Properties Research at CRL is probably the most SrnhnELy men appropriate laboratory for this testing. Vapor Pressure of cc 195-23 - priorisy 1X vapor Pressure of cc 795-23 - Priority l]I 5 Degradation b) Degradation Degradation studies on ce 795-23 will allow Degradation studies on cc 795-23 will allow Eo raga iStemce. a the environment estimation of ~ts persistence in the environment Lee pes and identification of degradation products. Proposed biodssradation studies, as a first Proposed biodegradation studies, as a first ee Tere toons Teokive roe oe stage, wild simply involve looking for an Theteints tonteptiotlon of 18 Skt: the most increased concentration of LR 3844-4, the most Ty Seseaation Fiosust. bv Gis 3s vas Som in likely ~egradation product, by GLC as was done in Fp Engrg Ht A the above described cc 795-23 hydrolysis eens Ee rege tras saeeberien olen eunrt experlr~ent. In this case, extraction with ethyl EE fovane iii br Mresseiey. oo omure ether or dioxane will be necessary to insure prea Rai AA complete extraction of LR 3844-4 which we have Hare LL re found binds strongly to biological sludge and oe soil. astooeseas 3MA10065525 1Jios00080 3M_MN00000080 22557733..00006633 sae-58- TAL Op -- Zf studies 9ire an indication of cc 795-23 faaation, ghee on Lnttention of og, 72%.2 biodegradation, further work will be done eoLe al Ee oh he pois involving specific analysis or cc 795-23 Eh epcacation components and other possibie degradation Een 2 hak Boneh a Fencrioes shove, products such as EAI 80021. As described above, Giesiess, suk og BIT S00,gn Tenoribes pinves, these specific analytical methods will consist of Shs Seam asty SHE Te Teta gas-liguid chromatography of methylated extracts, me eerontarer ot or, if possible, thin-layer chromatography of Salhi! radiolabeled cc 795-23. ALI proposes testing will be done sndec All proposed testin9 will be done under eee Thatsantion. conditions r~gorously favoring biodegradation. eeent teaes 1Snamie acts cc 795-23 will be incubated for extended periods i~ a mixture of compost and soil. Bigorcus Sot} Biodegradation Tests on cc Rigorous Soil Biodegra~ation Tests on cc repli 795-23 - Priority III oo streets c) Effects 5 382g Oaphnia bioassay (97) ang 14-day algae A 28-dam Daphnia bioassay {87) and a 14-day algae AnoSee LL test (8~) are needed to complete the EEapantes <Frongs proEieten thie impartans environmental effects profile on this important rome peeeeEies ng secibitn peines fluorochemical. Procedures and decision points the IT fetniadntes foc will be the same as those recommende~ for oH oe take, Shean fluorochemical surfactants. ce 95230 cc 795-23: 14-oy Niage Bigtssay = Priority IT 14-d~y Algae Bioassay - Priority II Td Nami 28-day Daphnia Bioassay - Priority II b mieshels Alcohols por rvnean--e a) Usage aniy 3 fav relssively smalisvoiuse products, Only a few relatively small-volume products, Sry soln sealielune pretuets cc 815-I1, cc 783-1 and cc 796-10, contain the aa free ~luorochemical alcohols as o~her than an Eopeter] alboiasri,er ten 22 uncompletely reacted raw material. Thus, the thea 1 Shis-1 ond in importance of the alcohols (LR 3844-4 and LR ra een tetany 4197-2} from an environmental assessment ere nati a omer wii sates fron perspective is mainly a concern with wastes from Erpieilee Ln rHtiLe omen it este manufacture and the possible rel~ase of these Dict andSe Terie rej of ese alcohols from the degradation of other products siophle trop, SheSrgmadagion of outer prota such as the fluorochemical acrylates and the SBcohiaseosteQouee2rpciaricnl demrlnses 0 0 re phosphates {cc 795-23) in which the alcohols are chemically bound. aunrossszs 3MA10065526 awunosotst 3M_MN00000081 22557733..00006644 EEcrmee-------------------------- -- ho -59- 5 mystical properties TAU b) Physical Properties ter solupia - Waser soli censuonents Water $0lubility - Water Solubility measurements EEL h41a9v7e-2been (1m 04)~eby 4197-2 (1~4} by ontheL~ the VVe3ei8ttt4hh4-4tteecc(h1hnn0ii2qq,u1uee03)((11a00n55)d),, LR"TThhiiss Hiaeeis seturios sates by rerliioiseins it process saturates water by recirculating it frre peg A Rr through a column of sand or glass beads coated RE tai ey TeeElr ehiaetanatesy. with a low solubility material. ~nfortunately, ptr ne All the technique preferentially leaches the more A IR soluble components o impure materlals from the gs column. This dotect of the procedure can be significant This defect of the procedure can be significant crepes foodie ~ith this class of products since both alcohols herent arn brigh are actually mixtures of several isomers which SiEely have altiesens solubilities bot ere likely have different solubilities but were seat Hetant iota Es tne hair iea] Sethas.saec. undifferentiated by the analytical methoO used. SCE he I Teron he So This lack of purity makes it impossible to eet eel LertoToeiins siators salubliity accurately and reproducibly measure solubility pei eee a te and partition coefficient by any standard ~ethod, 32 Bea Rese a but the Veith technigue is particularly deficient fray ri nr rv in this respect. For example, the two solubility Egy i i RL values given for LR 4197-2 (2.3 mg/l and 0.82 SEAS BEE a haters elections mg/l) resulted from ~wo seguential recirculations Rb tha tend Coates Selim heir these Sata: through the same coated column. From these data, Bn a Ber Te Sper oe it appears that the more soluble components came SECT A LL, RS, SEE off ~n the first washings. Thus, the 0.82 mg/l CEPR Sore HIE, Thtriatne os value probably more closely represents the ES RL HI Cana. solubility of the ma~or LR 4197-2 component. The tush of chuntosl gority say alse be the cause The lack of chemical purity may also be the cause ath T BI Ran of variability in LR 3844-4 solubility Shrines? BLA SHEA re measurements. Early, apparently repeatable preter gh ha so results showed an LR 3844-4 water solubility of bSrEeaTHpectS ed thaY mes ee ot sho GE eA eS 0.~5 mg/1 ~i02), but our latest set of measurements consistently showed a value of about 0.16 mg/l cetanoluates ractstion cootricsent - the Octanol/Water Partition Coefficient - The eee on ie rom miconet ~atltion cbeffi~ient for t~e ethyl FOSE alcohol EE io mot sesorately Khoi: but the satis of is also not accurately known, but the ratio of etae IT hae oceans) the product's water solubil~ty and octanol TI ot ra EE HEE solubility (106) indicates that the partition Soatticione in nok (sorsinly besvee 10 308 coefficient is high (possibly between 105 and Tam ne thE oo dag i07). On the other hand, using the average STeoateicReEd }sobthieniitiessyerosfsi2nh aSahuesrri:on6o.3f mCph0i]ou : aA RE Ce Teeater parsivion measured solubility of LR 3844-4, 0.i mg/l (0.18 ~M), the regression equation of Chiou et al ~19) predicts an octanol/water partition efhidien Ties Erte SR Be coefficient for LR 3844-4 of 3x105. The Err rl distribution coefficient of LR 4197-2 has been measure~ by the standard Environmental Laborator~ LLIN Tr Aen procedure and was ~etermined to be 5.7x104 (I07). auktessszr 3MA10065527 pr 3 M_MN00000082 22557733..00006655 J --s0- - STA These water solubility and partition coefficient Ter et nt een netic, data sugqest that the two fluorochemical alcohols would tend to partition from water into SEpe Ee ae, sediments, llpi4 tissues of aquatic Organisms, and suspended organic matter, such as activated qa sludge. Sod Sorption = 3 e318 amet were Soil Sorptiqn - LR 4197-2 and LR 3844-4 were EET el con re en, ~0una to have soil organic carbon adsorption crroeeessfppfeeicccttiiievvneetllsyy,,, Kwwofhcif,cchhofiinn3dd,ii5cc0aa0tteessandvveerr1yy5,0ll0oo0vw mm{oo1bb0i8i,ll1ii0tt9yy), in soil and is in agreement with the low water solubilities of these compounds. Preliminary FP ae SE ~oll TiC measurements were also made on LR 3844-4 (72). In this test, the LR 3844-4 remained at enn et SHC Lene the origin, which is consistent with its Koc and water solubiltiy data. Together, the water ANT te Sn solubility, soil scrptlon, and soil TiC sil else wR, measurements indicate that LR 3844-4 will have Spstihaa BLE Sy very low mobility in the soil environment. 5srsp - fron rpntsaste cern: ~apor Pressure - From nonquantitative observa- tions, the volatility of LR 3844-4 was found to Sahm ie. be substantial (I02,1~6). LR 3844-4 steam distills or coevaporates appreciably with water. These observations suggest that LR 3844-4 has a significant vapor pressure. Due to its OF momanion structural similarity, LR 4197-2 likely behaves in a similar manner. c) Degradation Chemical Degradation - Lab tests have shown that LR 3844-4, when treated w~th 5% KOH in absolute ethanol at 50-53~C, hydrolyzes to form EAI 80021 sea en erBY with a half-life of 77 hours (106). These results, however, cannot be extrapolated to Sai met mtheid estimate environmentally relevant alkaline hydrolysis rates in water. Alkoxi~es formed in eden ok eg inte, alcohol are much stronger bases than hydroxyls in water. This stronger activity can cause reactions to take place in alcohol that may not occur in water. Our present understanding is that LR 3844-4 would not hydrolyze at a significant rate in the shied alan teine environment since sulfonamides are stable in water at norma~ pH, only hydrolyzing in strong FRNA, acid or caustic solutions ~iI0). -- 3MA10065528 sss 3M_MN000000B3 22557733..00006666 re mc rr Rseisivesmataseirono,r- SmoOrRosEeLseuss bHyavee TIAL rte raretive sesurts (11a aki clon, the Pbotodeqradation - Photolysis studies by the Agrichemical Group on LR 3844-4 in DI water have given negative results Iii). In addition, the fitgh vig Environmental Laboratory has done two ETSI I UNS me rire photodegradation studies on LR 4197-2. The first proneEE lh involved exposing a saturated aqueous solution of E BE T ALL LR 4197-2 for 30 days to a 40 W fluorescent black ey es seis light (112). The second involved exposing Fri hs supersaturated aqueous solutions of LR 4197-2 to Ee ey ml re natural sunlight fur 7 months both in the Pm is tet 2 ppBhrhoeotstoeocnchcheeemniiaccnaadll ab""ssseeennncsseiittiiozzfiinnaggc""etoaapggheenenttnon((e11,1133))a.. NNeeiitthheerr RAG ey study showed any significaat photodegradation. Rr Tee Aquatic photolysis doesn't appear likely to cause IIS mn significant degradation of these compounds. A pigtolyeds stay on 8 844-4 sorbed so soit BRIS igh ent ive, "yet A Dhotolysis study on LR 3844-4 adsorbed (114) has given slight positive, yet to soil Imran iE PEI, socorpuion inconcluslve, results. In this study, adsorption nlite to silica could have lowe~ed energy requirements Sa for photodegradation. Sictagratusion - wo blodsseadation of etsher 1x Biodegradation - NO biodegradation of either LR Hemme,te on, 3844~4 or LR 4197-2 has been substantiated by FHA py analytical means in any of several biodegradation Rim, net el oan tests conducted in the Environmental Lab. The Tort SSopTdanStnd of HranACTL SL tests conducted on LR 3844-4 include a Warbu~g A ei sy (((711912)5551,, a a%4n1nd0a-dsaa>G6--nsmooennmttihhconssthhlaankkueeouffsllaassakkctissvttauutddeyyd wwshhliicuchdhgeuusseedd PD eete E rt es i eorothanscals 1S): theta seusies shov that inocula from a number of sources, including soil and sludge that had been exposed to fluorochemlcals (I15). These studies show that ED aptiiN T rapid aeroblc, microbial conversion of LR 3844-4 aR i Rly to other products is unlikely. Io contrast, peetlucesactane sutdonsc acia In contrast, perfluorooctane sulfonic acid RE EI EE TE ce (EAI 80021) has been identified in rat and monkey Leet Se PR a serum following 30 and 90-day LR 3844-4 feeding SSRI Rt derdo Eat Saisie studies (116). Its concentration was 300-750 HE reer cob hot SE Tobioual I Sobee times greater than that of residual LR 3844-4, nn Hah, suggesting that it is a major metabolite of LR ams raid ~844-4 in mammalian systemS. Due to the great BEdiversity of catabo1c capabilities in He mn microorganisms, this finding increases the BEI Hie HET DAE Moca probability that microbial systems may eventually be found that are also capable of this IE, conversion. It also suggests that FruIit i W-- biotransformation could occur in other organisms, such as fish or food crops grown on so~l in which Be rr ni fluorochemical-containing wastewater sludge has Srna been incorporate~. awstoosezo 3MA10065529 onones 3M_MN00000084 22557733..00006677 a. . -62- ad) moconcenteiaotn : L bSbR IItltSiioooTcthhceoaaoossnnncEccebbeleneenantaetnnrtrraaVacdadttesleieoummneoTLoRsnhnsst33ftra88rnaa44stt4i4ee-n4d4dg' titinhnhraeottttnhheffeii2siisr0hh0t-t~i5vwssi0ssl3ilululeetssi,,nesw wiittthhhe SSw wcTooRmhaEnnoetEeclce)ereennfv(ti8tasgrl,aah9utiei)oosvnnavluoSeToefrhafeselstceheirhanisinbabeiglom pmcinceaoganotnedtncerefcerirnoeniatam tnllrtorafa2iitnn0tiis0ooptt-hn5nehe0cei0ffaeascct.ittmooerrsssACEthe GSAdf(oBoaS3rCrtS5aTbb)eooooftvtfhhSaa2slumiDbiem pIRlslu viiae1legagewgirre1ihrl]eoolarrdddssteanueurdnrsnest.SfpiCisssFoonhhffdmveoom aanflrga~ugneccnhohitaotfaufnundsnesepselpel wwpceccreieraoareetsstfi.fiinffsosaohuhtBu:ninC. dldFy H b2bS20a0iiu50goos;,rccceoolseuwnn:nhcceeeesrrnnaaeettm iadrropssaa.ltteeesrrddBeeClhlLaEaLakdRttii=vva3Jee188ll044Byy044C0--F14mmoovirrnatteeooluberafafaaaittmomnttuifyycthhatCtpilgigpsrsrrrsseeeouusa.xeettissm eerraTtheilys dlLpfei~ir5gpnpa7rdood5e~ppt1enhne9,giislaiiioettc.cnhhgaya.ttmm,oaafttLLeeRBRrrCtiiF33haa6e8ll44=44r--qq1i44uu0uaa0tll0ettiiesentttnidaadinsttso.iinbvvrtteeasoollioyyniccaootnanatiggccirorseeseennnueettessrrd.aaetwtwiei~eectTihhhoiiipnnsed pbcT cSyroqheeseNdaftetiftreiciiolcctnyhiiaeonnnp(ttsrIe17do(()ifKKI dooi~rrt)s)ehelwatShctorI oielnBgBegCroFer.osfcsiH tisoahOOnnuuBoaaOlnne/FttS qw'iiuastcataattteaiiibrovovnueepttlladyyreto,inteta ethhleieoopned STeE'ST equation orde~ of nitude Manes than that observed. predicts whole fish BCF's about one magnitude higher than that observed. ScFCFililasseilhhannecchVlwlaaeottaiseernerred.d.doaaaccEl"ccxEeuxupBpmmeiauurr1lliiaamntteseeenunnddtctss LLiwvRsRihitt33hhs8644h44bbo--oou44ttdhhuuppSCcoonlhnnaaansnnrnrreaeeellnttcuuerrnntottoo 2TcsbSteahutaed8fatyib,solhaubtaussai,in9nnd5gg%SbrSolcoenuonolemcygyphilnblecccltehheaannsinnnui.eennllfti1ia s4ccvhaeattdftasdialyhysasoshnw.,,e(Thd8()sg3.0hhcoo~wweeaaAd'Rruasesne7Tcc0conle%yoend,dto SwtthhheeEoleRmmaajjbooEo~rRdyesSdaciiAlbbelElaeeranccTBcooRemmppooinnneennTftteinvedooff deaffvyiiassshhd,,(a9y1cc.liecpaoerrr~eeiuddosdc.l53e00,%0 ABoAfimomaaatjjdhooenrriaLqqRtuuieer3ssa8ttt4i4fio-oon4nn dbaitoacon(choenta4r1a5t4i7o,n rzwieonarmmkab~iihnnessginscaaae~bbeoouusttf~rvettehvhii-issdeawyofpertihoed.ra w5.ork21;sin2c3,e a34,rev23i,ew 41o,f atnhde raw tSSSNdoBoanhtaaadd#eea4dcmm6(heo2aNy6nsnBl9ss,,ti#rc4aah1pc0..ti9ee4et7a33,t5t5te))hh)aa~tt."snvhooott21whuuh,esseldss2thc3oqha,llautwevaeen2mnnt4not,ciossta2ottu5uek,issseevetsdess4l1,ywe((eoorraecceentxtdatandnrdooaoollcnntee mcR aLRlRntdc0or3on o8e0ro4tg4hr4-yga4lanntiiaffsscrrnemeoosstmnantfstseiuuo)sgatnhggewesostttutifhselssesdcauattuevhqhg.aeuattraanitWhssobiooorttmmmkeaeetioo~STvnniH!enIlgnSyi)nggext~trooact coetltleucleasr mater~al is irreversible (ll~). e) Effects BnBiiioocaahssssaaiyyhelddauatgtaea oaonncutttehheefiffsllhuuooraznoogcchheeammaiipcchaanlliaaallscccoouhncooillesss,, on oowDTbnnhhooiettcshhLLhsRaLLRhc3is8one4mc33c4pl88-uo4t44du44,,e-n-4d4sai(caannunnsddtddtiieccaoLoLtRtrRfeeis4n4haae119a97aTrl7-naa22dcch,,kkedoa2oaiff9pnadhnttsiaaoooalllxxuggiinaaccsilliitittuiyydsscittyeoou.ufsfddiieeossn ttlITTihoii)Eemxn.isiitetcsei,stcE8ygo0ccgm_-a~pr8atfo,ruyyn00d.01s1ssLate/ua3aiidnt8lidaoeoo]rsfr1 mS5songnpe58/pa0tlrrL1h,oRxtirh3"Sme8er3a4eisHts4rpTp-eeeL4lcscytotiliiivunn1veb/dael3iillylcytaiawttta{aeeytTvdsearbilnneeoo utSSstas1aouee5txdtd3ui" rcaaiiIbtttnniiyieonhotnhain.tiissnd2s`TTimtrhruiuuie~ldds/ciyylt.:iwwyaaossr TTshhauStiiphhbssepesrcoa~lhTxaaniicictggkkmhihaeaetstsootfefteldytcoTooobnxwyn1cii/cec3eeoniinttttwthiyyearartatehthiariasosonn S5ateel1srs0tto5sa5..:beeanv"~Poeortrienneadxxiaaormnpeppeclltreela,,yteda3sussbfeesomm~riiaccn1oot0nintatditiaenny~usuoouubvssyithasocettthSiei0rvv0aamtteeesddt: sludge system operated for I0 days with 500 mg/l" MAT00855%0 3MA10065530 a3wM_nMoNc0o00o0s00s8s5 22557733..00006688 -63- SMEAR. TN oS[oxeimcuilnsyiEtioetdheLR toxicity to the sludge 3844-4 sludge mmaiinccdrroooperrggoaadnunicisesndmss no(5a~0p:arenitn (ii ]~ In bioconcentration studies on bluegill sunfish and channel catfish {8,9), I~ ]844-4 snowed no toxic effect despite the fact that the ish concentrated LR 3844-4 to whole ~ody concentrations o u~ to a~roximtel ~00 mg/kg a acase or-tt Tes.t, x ps D~4u8pn-hHinr0iasTm~FaSng0nae Eseffee W -- w 96-Hr. I~C50 81ueql11 sunfish LR 38.44-4 wewaxactteeeerrdsssoolluubbiill~ittyy exceeds water solubility so et) me 0 3O-4ay egg-f~y(a) exp~ure ~'C(b) >20 ug/l SEU em Algae{d)14-day ECS0 o cell coJnt >1,800 m@/!(c) 0wan : ee LR 4197-2 im {1350 ~3/~) (c~ FScEUmFp om exceeds water solubility, , waom >100 mg/1) P~ference.~ {I,I18) ( i, 118 (119) (120) Footnotes: B ERLIIERA SSEMEA , oe cin sn (a) Fry w~re Fathead minnow (Pimephales pro~elas). (b) MTC - Minimum Threshold Concentration (20 ug/l was t~e highest concentration used). Bo Ene Ed (c) This concentration is greatly above maximum water solub111ty. (d) The green algae used in these studies was Selenastr~a~ Scaapprriiccoormnuuttuunm,. 2. peRceocommsmenenddeeddTTesetstiinngg a) Physical Properties Water Soiub|lity and Kow - More accurate measurements of LR 3844-4 water solubility, LR 3844-4 octanol/water partition coefficient (Koc), and LR 4197-2 water solubility are needed for structure activity work. These measurements ~referably should be made on individually isolated isomers. Work will be done using PA-a~proved protocols and, if available, radiolabeled fluorochemicals to simplify analysis and cut analytical costs. -- 3MA10065531 snore 3M_MN00000086 22557733..00006699 en Ct TAL WMaatteerr SSooZluubbiilllittyy:: LLRRr 343883445447---442 =- PpPrrriiiooorrriiitttyyy 1111 LR 4197-2 - Priority III Distribution coeffictont (Kou): LR 3044-4 Distribution LR 3844-4 ~ Petority coefficient - Priority 1(Kow): TcSSR|ooeTEliLcllYCo)m,,SSeooSnlr~Edupsiett/ndniisgoo"nnt'otth-~hese uSSoobO0li..sllS5t..aTTnhhtEEiiiPBnanA-t-LeLppaarryyioteetthrrooeccooCpCllrhherrdoo({imm17caa93t))tt,:ioooggnrriiaasnppthhhyayt AASFfrdahllessoucooouoorrrrmopp0omct1techlinhteoodeFnnenmeidirccddeaaaanttlltcOaae'saasoolulcbabcboemtososahhtniioaognnln]eesstddivaahhtraauueivsvsoeiieunntgsghlloeovtwt{.hphliirsussseoooidirllipPocrrcmtmoohoioccebobeemindidiluuclirraittelethyya.mtmaayy ~dd1sCIeehhcclteoooaeswnhrrsoommdlliiiannfliicfiinnoaesgnogromoemelenttrsrchheseee..sinrraaasttTmToeehohienelgssaaeennddevnssavitreeviuixxardottlouieeesnennstsmtefnwoowltiffiullsollmmroosouavvaccileehhddmmeeemnnisiittcsnnalooff TTPlltLLraahCCinneoddsemrffmieiielaltaalslyslsusucrroseehiaammonnnelecddsnenttssssltiiunhedoiogngsnseeoiLtLlRRyiipnne3e3cc88noo44ovrr4f4ipp--roo4w4orronaaramattkrrieieavnvetehsooaffssssiiutltalceeooishswvr..eeerrsadsySSooiiblleen pdsCSGoortatnniadaeeinon,,odrdlaiasrtarabdyldlettlhphspeororiduouongccgcheemheddauutpptrrerrhereiii.i;osoarrltsSSytt,oopooiielltthhoeefTTLICCwaAovvraarrkiieeqllqueauhibibarrisieellssiiattlyyreooaffdy8a been radiolabeled materials. Sot1 mics LILRRR 45411899769--k22 -=- pPPrrriiiooorrriiitttyyy I1TIIx LR 3844-4 - Priority III SoVVVbaoaEsplpEoeaoSrtrrTivTlapPitarrzieeteossIsnssosuunrrfseeriTonnn-da-ituccSSaaaiitttnneeeccree,ttphhpGraarutteeallniiLLtmrsRiiiinn33aaa08trc04iy4y4v--e44llaambtrTeoeoeararssdaadoittirlosoeyryrnyyents 2vonffeoe3eladadVv4estaa1dsipp9loo7irrtt%zooeppsmDmrrooeeeddssfleessrilluuocrrmaeettwhheeavaatnnadmmdrrooi,vovasueeqqsrmuqueeeuennoeacttunnusvteiioorfftvvoaoontllttsiahaheviittnessiitlleiimccltteooyyammpspoouaauurrrenneeddmenaatnnsdd mSECLc8aooRo3ymymp7p4aha1bPreer9rt7to-Rmmmp2ooeeessnnrtttttbssieeetesf4wafFnnefiddeRicencisitteeehhvnaeenarttrcllaiahyytot,ummsooppsseCeppArrehhLffn.eeoovrrrrieemmr..eeoddnmeMbNbnyeyetaaaAAsslnnuusarrileeyymmeeteniintcctsaasll VaVaraanedppoorrpPrroppoprrpoeeesssresstduuirerseeforRaatennsddeavvroocllhaa,ttiillCiRiLzz.aattiioonn mmeeaassuurreemmeennttss are proposed for: LnLpPa33i8044r44--e44 -C= Prpreiitcootrriiiitzyyy ITn LR 4197-2 - Priorlt~ II b) Dteeggrraadsaattiioonn SCCa3hhl8eec4mmo4Hii-hc4coaalEllihcasDRexagonrn,D"ealRgdyraadtTbaIihetioeeonsnne a--mefaaiCCtsnhhuieedmrmieiiensccdgaaslliinsnahnmyyttndshoeorertoollppyyrrbsseeeiisssseennooccffee LoL~fi of RehSSaAaxolxTltpcEEfolra-hiapTlocpoTilaoluviblaeeciacsset.eteKd"dOtHo.MTttehooterhreTeeeehsstfetteoosiinrremmveeaai,,ttrfeeoinnttmdaeeesiesnntnntvvesgtiisrrmmooaoonrncrremmaeeeennnnnttoeddaatsiillerrsbeeeecc.ttllyy applicable to the environment are needed. 3aMMAA1100008655553322 33MM__NMNNG0200000000088T7 22557733..00007700 SE -- = < A -65- TFFTpiey~ies'e'ssstr.tiionn(ilguguyppsuusnttn'ododueelprprtEhnhhii~1ll1gng))hha~wtteaaerm yymepapbbeseeerornaaatnntubueelrcrceeeeessssstsaia((ursruyypep tttztooooanoo66eb0b0:ssCee~)rrvveeaanndd KSKhiinimnnyogppodunoowrlirroleeftslddiaaygcgnnseaettisntoobbfw eefmccioaattthhduuheesesineeohhfyaiiyttsderrrenoiiovassilisyyroelisoinikinsskaeseblelrFlynaeyattteaet~tlooimoodfebbf eeegLL~RrRctrhaahemes33a88em c4m4. 4io4o-os-s44ntt 1s is for psEpthhhnhiigpooiseottnrooitdccgfiaehhecngegeatmrem.inaacdaitcaasaltmItl.ifi.ooodnhneyTTdooottreefossddttleaassytntesev,ihh,irsaaovvnnneeeiemisitsstehhhhonoeoestwwrraennrl m mvdtiteihhcecdeergr,nmoorbabitstdiaoocaaltltebbioemennnpootrrsfor ahWwhiniEaamdlTtlpl]tfot--rlobTtbeiaeinvvitemamd.sasieddneetuuinnIfddttyeeoo:rhehyeyxdxnndtrtoororrrromlaaalaspypliyososliliassaesttnneveviipsirrffoooiiomdnnnbsumdsdeceieintnnrnsttgvg.eeassldl,ttcocoooappnntrrdsteeieiddtmtiiipiccotottnsnss and to identify hydrolysis products. hTEmTaahhyiilissfp-lllttaieeeyfss'ettsiinsnngingcnocrcceeeaanndoootgslmhiieievvsrneearnmooetenncclllhyytaaosnlaaliennsamnuausttppppeeoonrfrfeuhthllryyiiaddmmlrriitootlipyyhtt.saooitssFor meaSBSya1xloay0anmnm beeeppitllaooaeelfyr,s gm SGaoeeeerncmncehoheroararatenanlhtilseadmrnoaassmccmiiidassnd-uuta-bccenbahhrtasiseaeaarls3oshlhhheyyydiyddnradretooroltollhyynlyesyeseiusisiestissnracvclhibaayrtytaoapnHHll"yu.sj2zies0oenedtsFOr NwbReyaoudumlildedotlannalobostetleobbrdee mopsaptetehaeeetrrdeieddemlatuuweppirlibblayylsfiiannccicnirrieeiaatthsseaiitnneggenvttthhiheiresoBnim.ent Seating. Ra@iolabeled material will facilitate this Pterosptoinsges. hycrolysis tests: Proposed hydrolysis tests: LLIRRR 343018494474--7442 -= PpPrrriiiooorrriiitttyyy 1I11I11I1 LR 4197-2 - Priority III TBPi3hh0noo4dR4tti-ooc4lElayyteirsEioalsnys o-tc-chhaAcaAtturpprrsoeoewrmvvheeieinoouuppsshhsooettsssoeottddruueebddgyeyyrzdaahhddaataassottiissgooiionnvvieelnnooffaanTLnLReRsting C3ttfoooo80n4mf4Ssmei-ie1ra4la1asis1ucumearrateeyalsseaoattnhhcndeedcFuiPOprnoarrhrioowntthsssooeii.llnllyyiissccaiaiadsssosgereoollfbfedL5ii8Fss t33ort08ee44csci4ooo--imm4lme.enanaddddeesTsddoeorsrbtbtteeiooddng confirm this finding. TT3F3ee8r8s0so4t44nt--ii44nangg"oSonwownilivllsselliinlltiiii,ccnnaavvsoolsplsavravneneeddapdpoolilrranacgcPiiprnnraeggeffteehaarriaanttbbhhlliilyynnavescsc:ioiollasoiittfcciiaannggtggheeeoollff LLRA VVc1Cfy3yoorcacnotootomenarrdedea ysacsceuooouabnlnbrtsvti.aeatrniiratnnat,eetTrreeh,.esoopnnacarnnoeddnattthdheseieeinxxngpbpBeoooorssttaiittnnooutggnmsheidonottffoowliasssalnhuyulennralaliiiibergrgohtfthtiitggthhfhftteoorr uupp tFtthoraeanonsmnspeapaxariyremeenauntrtm. ettnoovTihssreuuonnnlicmiioegennhhttttaailnddeoodrwwenngursttaeoodda22tw99ii80lolnnnambTeattcooe.ppeerrmmiitt the maximum environmental degradation rate. PPhhoortteootlleyytssiiitssy ooTffur LL~R 33684444--44 on on SSiilliiccaa GGeell oorr SSaanndd Priority IIl 22557733..00007711 Em 3MA10065533 au WNooooosss 3M_MNO0000088 = "oe Ja -66- Sisgesrasation = wyarotysis, photolysis, ans Biodegradation - Hydrolysis, photolysis, and Ee ies Inde: Doserataty ciporous biodegradation studies Under moderately rigorous EE Srorasscion of conditions have not shown degradation o eral Simi ieetas 1 pessious testing envlronmental significance in previous testing. Fheniin Wh En A need exists to run'aerobic microbial Tn Sonatas cosas She. ghat rigorous biodegradatlon studies under the mos____~t rigorous Precirinnpabins ails hinged conditions conceivable at moderate cost. Such era. et onas 1 Seetralne Sheines studies would allow us to determine whether Sainiribi Mat Ei. measurable blolys~s might be occurring in the means out wae pbsiescaie Sasi ne environment, but was undetectable under the ee, ET i Te. milder laboratory conditions of previous tests. me proposed bisorgrasasion siuey wit mostty The proposed biodegradatlon study will modify eit te ney standard soil burial methods by simultaneously PI Ar rh bomposting organic material with the soil. This a approach, which increases microbial activity in HERE Neen e Sresely Tocetast are Felistent "to degradetion(1a1) = the soil, has been found to greatly increase the degradation rate of organic compounds very resistant to degradatlon(121). This study vould be grassly facilitated by the This study would be greatly facilitated by the Ee TL SE hse use of radi0tagge4 LR 4197-2 and LR 3844-4. This ee hier sumer would allow detection of 14C-EAI 80021 or other Sopiaattion reteete es me iF ne Labes wart on degradation products hy TLC if the label were on rrri Sa I SAC the perfluorinated portion. Zf the label were on He pens ie pelhes the hydrocarbon portion of the fluorochemica! RE i HE Sy alcohol, 14CO2 evolution wo~id be measured, and TE This Sadioeces Simm Eieant dngasetiont the if results indicated significant degradation, the FT Rr RE RH Le program would be expanded to identify degradation ann products. Froprusd rigorous seid aerobic biodegsadesion Proposed rigorous soil aerobic biodegradation non testing: in 3n44-0 = priority 3 LB 3844-4 - Priority I Bay LR 4197-2 - Priority II No study of Lt 3844-4 siosesradation under No study of LR 3844-4 biodegradation under a te et anaerobic condition has been done. Rigorous SRASESBi: SEE act Miko ecorsindes sich 08 anaerobic tests are also recommended such as eben oe eninantanr mixing 14C-LR 3844-4 in river sediments or TETuatceines seid daorispentes sion slsester water-saturated soil supplemented with digester ae ma Seer RATT E00 sludge and adequate nutrients. Such testing aatiTans Jor sveveatic would provide optimal conditions for anaerobic ied ET he degradation. It is relevant to the ET La Ene Tne Stet soaunisivy. flsorochemical alcohols since water solubility, Err e Ms octanol/water partition coefficient, and soil Fr a sorption data all suggest that the alcohols are ira rn Sntr is likely to accumulate in sediments or soil. This Lea art i, Se Se TE Th 1d testing woul~ preferably be done wlth the 14C Hel RRL SILT See label on the pPrfluorina~ed portion of LR 3844-4. aunts 3MA10065534 a ossocen 3M_MNO0000089 22557733..00007722 --67Proposes aerobic Testinas NTIAL Proposed Anaerobic Testing: us Saeket = prterisy 18 LS 3844-4 - Priority II Blosransgorsation = The setsboltsn of ia 04t-4 Biotransformatio~ - The metabolism of LR 3844-4 Blegrmsformation| he Setinclisn of 18 Js, by fish has not been investigated in our previous BE Taveciaad,1h,205 studies. Zndications have appeared in the fhysier, dications hs,spppeessin,Le internal 3M literature (122,123) that this Be erty sastaator fists: 1t process is operative in ma~alfan systems. SEoSree 18 peebys Be petier net lly is, therefore, recommended tha~ simila~ studies Jr Shaestorty srr? hay pti rnin be done on [ish and plants. Fish studies could Bt goreon, Bi rE pir etn Serie be performed alone or in conjunction with other FEEL RSARR long-term studies such as fish chronic tests. Aceumuiation in planes is of signiticuree since ~ccumulation in plants is of significance since Sop Sli et ei food crops are grown in areas in whichLR SL Ta 3844-4-containlng sludge is applied. A rehome Ln b, preZ~mlnary study of accumulation of PC's, Be een ot, including the methyl and ethyl POSE alcohols, Tbeiion Fn a hE Tuk den into crops grown at Decatur is now unde~ay. [Er Samples are awaiting analysis in the Commercial SRE Ie Rape Teal Decoy TSH Chemicals Division Analytical Laboratory (124). Shemicats, Dlvision Raripticel, oie Looks Proposed laboratory studies will examine roots Des soreloey of i Tis sovseves and aboveground portions of corn and soybeans er Tees Ea Bhat grown to maturity. Again, radiolabeled LR 3844-4 at should be used in future studies and plant tissue leh nl ann rn assayed for parent and degradation compounds. Information ron this study vill be vred to Information from this study will be used to bombay estimate environmental risk of sludge s~il forimmie sruivnens,sie of ege, incorporation practices. It will allow EET Tories vagetailor arom at determination of whether vegetation grown at EpA these sites coul~ uptake, accumulate, and pass Bereer he wae ass . fluorochemicals into the human food chain. FE Ri np Kal Abnormalities in plant growth and development tonoempticios Lo plane gover, sm Sevelopten will also be checke~. The study will follow Erecpgoged,sitanddard Pregrssgesgteores if vessotion proposed standard procedures for vegetation uptake measurement (125). Secpones fan blotranstorsation stuetest Proposed fish biotransformatlon studies: 8 3004-4 = priority 131 LR 3844-4 - Priority IIi Fropotes plans upeake and biotramstornation Proposed plant uptake an~ biotransformation roe studies: 18 1004 = petority 11 LR 3844-4 - Priority II f-- 3MA10065535 summons 3M_MN00000090 22557733..00007733 a a ei SIA -68- ioconcenteacion c] Bioconcentration Fish bioconcentration date are suspect bectuse. ~Ish bioconcentration data are s~spect because, Tea meee pe ely re soe seriass as indicated above, no checks were done to show eeEr Ton he ks Jorn. Frost in ~uantitatlve extraction of LR 3844-4 from ~ish Fanti xtrioonf Mattias Sen tissue. It is recommended that such checks be Sovtisi che Hume Teneo ants ovate sogirs done at this time. Testing would involve adding frst. lE HI ine an tre a2 LR 3844-4 to fish tissue homogenized in water, RIL; Eien tage pomogenie 12 ve mixing for i hr. and 8 hrs. This would be TeriSben br ncienting Ith br] sovagee and followed by extracting with ethyl acetate and Es a hue tins n-octanol, the solvents used in the fish Be as? Jt ELE cena. bioconcentration studies, as well as ethyl ether, er i anEirt, ttt 12 25rdeo a solvent which unlike the other two solvents Satartes Shin ant te le extracted LR 3844-4 quantitatively from et tL De SHE wien Microorganisms. Analysis will be by GLC with mee DEE peat oa 3} electron capture detection or by the use of SoTL radiolabeled material. Contienstion of ish biosancenteation study ConEirmatlon of fish bioconcentration study st extraction procedure: ia 304404 ~ priority LR 3844-4 - Priority I 0 sects d) Effects i recommend expanding che bioasaay Sats en In 38404 0Tth a 26-day Japhnis bioassay. Fis We recommend expanding the bioassay data on 3844-4 with a 28-day daphnia bioassay. This dLdRaattas Sn Bn will allow a more complete evaluation of the ShienTor SES eluate environmental safety of the important RE A flu0rochemlcal alcohols. This testing is needed eae Le i parently Some fas to determine if this apparently long-l|ved el environmental contaminant causes any long-ter~ orignal Som ann toxic effects. Tests on daphnids, a Fe Le representative of the invertebrates, are BE Eh iy re particularly useful since they are generally more Ee ee rir eer Thur ard sis sensitive to toxicants than fish and algae. a eee hrnatis. E"aoR pmeth 2L02,lSH,EL ST corer Shuster are SonpIniaEeTaaps as oryetec to These tests are also much less costly than other chronic studies. Daphnia manna life cycle studies are completed in 2~'days as opposed to audi bre comeisnee nine months for f~sh. 2t-Day Bupha Sicassay 1h 3844-4 ~ Priority IF 28-Day Daphnia Bioassay LR 3844-4 - Priority II 22557733..00007744 unicosss 3MA10065536 sucsocst 3M_MN00000091 = "es -69- Fo A1.crylbaatcehsoroung INTIAL 4) cresteas chacacteristics a) TTCThhooh5eerre~e2m3IuiHmi8lcaaattEfleellSudsC yooxorhlrppoaaorrconocrhatshdeusecuem ntcteiatiscnscr;iad.asllteicTahauscehicryeiry.yyilliaacsyttooeiennnttghppairrinonosdgdeuuccmcoocitm mtsssppsooaannrerieeennnttassll SPollymeirs." Elisratnenical oneeining acrylate such as solvents and emulsifying agents in addition to fluorochemtcal-containing acrylate pTlShfholleeluoeyoramaroreccocrerchvsyyheoileniaamititceceeaallpproollsa"yytcmmrreeyyrrliMssaatcoeeaarreeaadnnmddmaaddcs(eeooEmmpmsftroorrnnoiomnrhheyydddCrroolccsas)rrbsoonn RSBehrens in the Rose ihpockont acrylate monomers. HeFOSEA (C8FITSO2N(CH3) CH~uB3sc-oOc-hC(eOn)iCcBa:CRna2n)oneJrs(1t2h6e70"m"ost 1i7mportant PTTTphoho~eellaurryyoeemsireeorrocaassrrh::eeemp~ottcewl`wsamooymlurule~tlsmryydiospploneeanosns(mteaooshrnffne(dds1esa2scsc6ooprr)llyyo.uulllttaayiittmooeeennriffppzliooeuultdocyyrrmmoeaeeccerrhhssees.:mnhiiucclaasTTllihhoeens SSefirnrmoioouunbEmwl"ceasiti3r2ooeo00tnrn00)),,00pp00oohRa00lalatyvtyeememtSeeoorrrmEossoggorlrrleeee((eccaatLcuutthhulieeociaarrssarreettPhhebpwoaaeieolnrigilygngymhtnmsaetseesr.srmailtizllzr(0eileaMsiidnW)oo)snniaI..nEnsrgaannoegrigTmrngihiuoeeanlnnngsyiicons solution polymers (those polymerized in organic solvents) have molecular weights ranging from 551008 0 300.00. She i Tanges are eitiraces 20,000 to 200,000. The MW ranges are estimates SlicLe Lsere ae zeally Little fare sats on since there are really little hard data on hSTMTuhhWeneearEssae(eeca1tc2Etes6a)escc.d"eryyollEvaa]uttueeeoScreoppovcrreehooeeddnmuuciccoitctnasasttlammmaiasanyyilaccnooaatbhlloessls0oo ycc((ooasbnppnetpotartioieSnxnrh..esssoo1Iem01n1)ete.,t STEapenrnveodoviedirdurtocChoontihnsssrvme.ienrnlcotoanLawLiooloelwltlnyyetmmvaeoessllliiaeggmcnnccuuoiionlffnacaiiterrccaraamnnniw'wttneeaitPngaehAthsxaEtpnpeemccacpcttyooomlmpypoboomaeffneneretttnsnhhhtteeesssssemeaoatasrrseetusoeoff psImtsTeoohhohsretelabyeylulrubykeariiornTleeeveiisoiet,ryylIooi0n"kaarenpmenelsoedl'rynyatvEviaaatttslopopliooyrrbbecueoelpnpucrcmraooeoeeirrsrrsnesensguutrrmmtneeouihe:,bbaoiinxlliaBaeecnnlp,,deootleeythhttambaahhieevveetsiriyeensnlsggaa.rrbheheeiicggmabThhohuoeeurrssrreee. SSmabEleceeaimrctkEbayeeEiurlulasaasytenteReeetsooo,ffpoopIllpatTyyoshhrmsseeeEeisirrrirtssbh,,lnhriyiorgguppehhgeechrcanNMuWseosseeeri0.naangneiadaantrrttreeoottehxheeibneniicoio.rrtotleofilligfniinieskkeccrceetatillslnnyy.ecssttssoo,.Thuttshh,ee 5) cmayussiecaslignpirfoipcearnttiesa~verse effects. b) TphFPBhrrhreeooyeppsleeiEErcrnntaivvcliiihieezarssonoPimnrcmmdeoaeeaaplntntetatsraa'tllsiooiennrsLtuaascbbcctreotyhyhelala,sasatceegsteennpnipeoeosrlrleyaya'mtrtpeeeerrrddosss..unncooesppBBhoahyisytesesesdiiccaaoollnn itehP lthhieeel~tliietrryleH yRicmWhtts,eoem"ihth(cahahaveveleyey asaTRltrooereEwvuRcwswetxaaxRupttpreeeeEeccrr,ttSaesssdotcHlhhueEttusboobeiilhhiiapastvrvyyeeo.,dunSnce`eaotcgnnsdtlsiigcatbriiaaebbsslieeees4 oonn volatility and little mobility in a soil environment. aatoosses" 3MA10065537 aw monnotez 3M_MN00000092 22567733..00007755 [-- oo or c) Degradation The only signiEicant question w~th acrylate Frat By polymers is whether they will break down under environmental conditions to release more environmentally significant low HW FC components. As a general rule, FC acrylates are more stable (they depolymerize less readily) than their hydrocarbon analogs Chemical Degradation - Due to their known chemical stability, it seems unlikely that the acrylate products would undergo rapid chemical EE degradation in lab tests simulating normal environmental conditions. The products, however, are known to degrade in strong base BEL SES Rot erat sci hyarotyres 430) his but are not easily acid hydrolyzed ( ). This suggests that the acrylates will undergo some slow basic hydrolysis in the environment. Photodegradation - The acrylates (e.g., MeFOSEA!BA) do not discolor when exposed to light (126) which suggests resistance to Eateries and solid manufacturing wastes photodegradation, but some such degradation is possible on sunlight exposed fabrics. Both waterborne and solid m~nufacturing wastes containing 1uorochemi~al acrylates are not likely to be exposed for l~ng period to solar radiation since the high M~ of these polymers suggests that they will not volatilize and that ~hey ~ill mo~e into seaiments or be buried in soils ~here little ~olar exposure is possible. BBbIiiSooEddEeeI@gErrNaaAddaRatEtiIiooonnn -1iasThloeovw..likeEElvvlaahllouuoaa~ttiiooonfn oroffapid b~odegradation tests done by the Environmental Laboratory, however, is complicate~ by the presence of biodegradable surfactants and solvents in the tested acrylate products. In all cases, though, the extent of biodegra~ation can be explained as being solely due to the nonacrylate components. The lack of ready lohestasapie HHT TT 20 EE Lh Tikes are blodegradation is substantiated by the fact that hydrocarbon acrylates are generally not biodegradable (127,128), and FC acrylates are likely tc be even more resistant. aus 3MA10065538 sums 3M_MN000000O3 22557733..00007766 ne ; -71- ITAL @d) treces ~ffects dElElaannatrrvvagglieerrooannrnnmemuueemm~nbbstteeuaarrmllmaoorffeeiffzffaaeeeccdccrrttyysslliaantttteTeeeessbtptpslrsreooddhhuuaa1cc7vvtt.eess..bbTeeheenSinSosommddeeootnnaeeboolffeoonntthheeaassee dgpPPSaroroetololcauyuycpmpmesseenarrrteappgrrtteooososdgdguueuemocttcmhthftaeessrrrit..zhcceeoo~nnttsIIttaapiiienggnnciiTiiivvnanfeegbgissleedtthhttaeehh1ece2.rssywwaeemlmeeeiiaTgghthhieaattsccrrpyytollalaabyttlseeeers in nptNttoehhheteeresscedeenNinoodrtdnnaaaeaattgcqgaaetuusleeoayoeurruoseersfepccfEtroOoohemmr~esppeoOsffnnnopoteerernnmcmttuitulhfloeoaiafftetedetdseoeaaaxccppichhrrcrooiydpdtlpuuryarccootttdosessufu,,ccpttto,:hltteyhhmeeAAeyyssrsddoo in SnsftBooohlutelluovvoceemdronnaiocttjrchssoeherecnmtaaiilnnccdcdyaaaullsssreuuerrpaaffrcocaaerrfccsyyttlelpaaanarnntttotetedssu.tcphpteooiilnnlyyttmmototeexhxhrreiiesssccs..eieittyypp.rrIIonnoofdduuTffcchtaattehccssett,,daaatrrttaeehhee ooFtnnhllleuyyrmoaaacjllholleoronwwiccooaannuleeseattoocorfyssleepttartormediiunpncoiitlmmyuutmmsoexriLLscCi:i5s0tey.vvaalluuTeehsse dffaootrratthhee fluorochemical acrylate polymers. OS5oa8nnhnllyy3ragoqudouoannaeeettriiacctaaeccrlrLLyyyCsls'lg0atatotexevviaacppllrruuooee(ddsuulclcceoottwwApeeffpnnaaecommnuuiidsgllihhyyx tt((ooc1co)c.bbee88005cTc5-hl-l1i1aa4s4ss))ssiiffhhiiaaeeesdd GsSacusinianviguleismnieekiokssefdelielycrylTaaiinttttttetootllleeyTcreoeanactccccooohehnxnncictceettrrrhhaneen(tsiasaesoeiqqinnuunsAcaca.epettpiieccttnchhdceeeeinssnxeve8vi0ir5ppIo-o)rrn1.nooe4mddeeuunnccTitttthsssisnAinonaarwree mmSbsbaaoeeiddxilgeelnnneg'giitfttooiaaycss!asdsGneeeetstscsseeeerrcddmnoiinnnc((eeeLLnRRtttr1h8haee18t85i5ll))oiinkksaaee,nnlldyy aeccncnausa8aet0tt5teoe-fmm1pp4tttihwwsiiis~lnllowbbee cause of this toxicity. osTTafeeecssttttii`ssvvFaalttuttecoeorddogdcieeshtrlueeeuandrcgigmaceeiiannleehh-aaavvttceehhteeyaalalalatsscceoouutteepbbreeoeettdnnoourxciiddtccoosnn.eeeeffffooeennIccnttaassalnnluuttmoombbeerr CossCcofllaanususdecdefsgesel,s,enutorrrrttaehoehteescsiphpoieippnrmrrrsaiaoottcddiiauuloolccinn-ttkasesclrrryawwayteteleerrtssaeeotearafftteooaupucnnrpphddorrdoouddwnncuuooatctctssttt.ettOo tIriinennahhatiilmbbleiinttt sscyyossnttceeermnsst..rations likely to reach waste treatment NOmON-aInnBtBllueUyyFrPiOOooaSSnnlEEee,AA,,Ef`llsuuiioasooldrroossccoo3hhsllee~dmmciciaaccllasoollnn1ee3-aa2ccas6csruyyllaaanaadttpperreoocddemmuuooccnn8ttool:.nmieelr-rlTTehh,iissis mpPBarrltaaeccerttiiiaacclaa,llnlllmyysnoelnndloonntta0oos2xxii3cccc5.. 8m1a3IIs-ttts2s.6aaccauundtteeccS966--~tHIrri..I-1LL6CC,sSo0 fathead minnow is 235 mg/l. 22557733..00007777 3MMA1A010008655553399 SM MNGS000094 3M_MN00000094 "-722e- Sia i we svvoeveeerFrrsAnTSSTomauASniirTdoPs wmSgmiSav ooulzha Prcduct % this Polymer in ~:onagueous r~nts 96-Hr. LCS0 of Acrylate Assund, r~j it caused all the ~oxicit'~ ~m~/1 ) b sss sm ees rms 95 mor P~odu~s Con~ainin~ the E~nu~sion l~lymer: 95/5 i 5: 52om LR 2485-2 19 40 125 ers 552 A % CC 815-1 33 20 & 51c E E 38d 96-Hr. LC50 of Total P~xluct ReguestNo. i~J/l) or (Referent, 400 1250 131 339c 249d 2485 1204 (129) 43e 284e cc 8110-92 42 eo cc 805-15 27 34 180 (130) 2 E 34c 179c iE 22d 118e 34e : - 25 170 (131) Re cc 805-17 12 cc 806-6 55 cc 805-24 38 : - 33 689 6814 46 233 5785 78 527 (132) cc 8010-32 47 cc 811-17 54 pe cc 766-29 20 s It i v i Products ccataining the emulsion methylol acrylami~e cc 7811-I 5g ees rage mii Products containing i~he eradson 66 71 =i12c 26d ms, polymer: i>295 polymer: 575 440 ai132c 283d WA rtm 49/29/16/6 MeF~SEA/9inylidine ir>Ioo0 Chlorc%orene/EtF{~EA 6363 6671 ir 4068 chlori~e/ODMA/~ 4625 CT wL~ma25s6e3-a3 5500 116677 660000 22556633 487 1750 1204 mi 3MA10065540 3M_MN00000095 22557733..00007788 I a BADE mm prot Pynee [mT seE ena tao-- g lct t ya ATnSaee Prod.uct % this Pollmer in Nonagueous CJ=~nts 96-Hr. LC50 Of Acrylate Assuming it cause~ all the Toxl.city (,g/l)b 96-Hr. LC0 of Lab Total Product Request No. {m~/l) or (Referenc~ rats contain th solution ye: 50/50 PENA, 4000 8 Products containing the solution polymer: 50/50 MeFOSEA/C.W. 480 ~ cme ain EsaAcs win cc 824-32 67 >600 1132 1695 >2000 3762 5630 8021 (133) 1204 [Er os 2 an cc E13-17 9 ."" 9.5 286 6888 rcs contin he seen es 0/310 WIA 33 Products contalntng the solution polymer, A~late cms om = ~c 805-15 27 25 cw om 0 cc 805-16 77 >300 cow cc 805-16 77 28 cms ow = cc 782-43 48 130 rotus containing: 35/35/2010 NTSB PARSE ln Pro4ucts Containing: 35/35/20/10 YeFOSBA/re~FA/PoL~eg wes eo cc 803-15 36 >360 nets cnainio: 70/30 eros 758 Products containing_: 70/30 FeK~EA/C~ 750A wae ow 200 II~ 2256-3 1800 ets containing 50/3 Beso Products containing: 50/50 Et~M~EMA/(3~vA mw - cc 794-2 50 45d tts contain: 65728 tercmE Pr~xgucts containing: 65/35 N-Me~M~/ODYA cman cc 8011-235 I0 cman aos ~: 8012-41 >1009 roti cnsanion 7525ress te 36200 Products containing= cm ow 5 cc 782-14 80 75/25 Fe~SE~./Alfol 162~A 95d rotacts cntinin parses tele 38e Products containingMe~DSEA/Alfol-1620A ged @ [2 2543-4 95 479 400 wn asm 170 (131) sue>i000 woe 96f 5884 2 ax 328 4200 208 CAR -2000 DMA/BA aoe se >I000 5546 son as 9000 2256 we wo 180d (134) 0 sas 140 2485 we on 184 7~20 ww 23~d 4197 94e fd ut 1200 1000 2456 2256 auntoossses 3MA10065541 Snes 3M_MN00000096 25730079 2573.0079 J TC tee nl 5 BLE 32 (continued) iY vue J pa wer om 96-Hr. L~50 of Acrylate Assuming. Vp FURR wmeps im, it cause~ all the en me EERDE SE mi oxicit~ (.9/i)b 96-Mr. LCS0 of Total P~x~uct 9e~uest No. Or (Referenc [rp Products containing 70/15/5/10 PeB3~EA/Alfol 6120A/I~V'O~ 750A ---- p -- cc 805-14 35 3.5 22 8185 rem aio 57 ime Products containing 50/50 c~lorop~e~e/Et~ wmes p2 B omom LR 2563-3 50 167 600 2563 i BH 487 1750 1204 362 1300 2485 ris cn 4.7.38 eS Prc~ucts containir~ 55.7/28.3/15 .~E'CSEA/(EtE~E/TDI/~3PMA]/B~ pst we ?-/5-27 93 179 480 5508 ce ii 5355 BE A 651 Products containing 25/25/50Ye~EA/(EtEO6E/TDI/I~3~A)/Alfol 1620A Cue po wa cc 8111-4 40 >800 >2000 7461 a er N Ru P0SEA Mor~er ---- - mw CC 813-26 i00 235 235 6813 se Footnotes : 3 RriEr S 0 peSn st, re er son Organism is Fatheaa minnow, unless noted. EE EERE Er en em on Ass~ing no synergistic or antagonistic effects, this represents a minim~.~ 96-Hr. Rainbow trout (Saleo gairdert) LC50 for the~olymer. The actual LC50 for the acrylate, hc~er, is likely to be much higher. $e hen, R~inbow trout (Salm~gairdneri) Bluegill sunfish-~-~pcmismacrochirus) H FER y i ir 105 ot ee ts The emulsifers ."~een 80 and S~n 80 ~hich make up 1.5% of the product were replace~ E REE TRThS ma ses by$iponic 5-4. This ~.~iI change ma~e t.~ product l0 times as to~ic. Toxicity measure~ after solven evaporation 22557733..00008800 ass 3MA10065542 snc 3M_MN00000097 a Ta -75- 2 LATIAL 3. Bscommenges Testing 0 mystens eopecties a) HNe Poohysppihhe cyyassliiccaaPnllropppreroroptepieererrysttiiieeasstettpeeosstltsysreaarcrsee.rreeccoommmmeenndceedd oonn bfelgueoardoacthieomnical acrylate polymers. b} CR C~SDhIcehektgemayrsiilacaidcatnaaleetsiohDndyee rdBerroaldtregcyaaedatsticoniiosomnern=a-dtC eeFMdee.oaafsse ouTrrtheewemsoseeennrTtteesspGpeartooseaffsoennwtttit~haleeatltiivvee FShaeSyyncaeadartrrbyeioollaelelatyytosesiueisisnsaeet1srrocleaatteteeBsrisste'icesoomo:nffamtmeeettn`hhRdeeuuhaesspp.deepp.seecprprrrrvooTlHiddhiisueumcncsciettettsssss,daoaoaittnnteacottwnhhieselalndes EMFeffeeeonolFRrvrsOoicSSrthuEEohilAAniae/VsmCsCe..nLtWNtLee.:aasalittgii44hnn0p0tggH000'0saae.rrmDbeeuMelAn..sT39ih35o7/en55MKeeaFpFMcNOoOereSlSFyFEvEOlONeASaS/e/tEEEr~eAAAAs/C.BEvAKariLssaeasaca.nonaddminmhneii53gng00hdh/7e58d00 BPmLII1ytoRUeRlreS2iLo'csT14Syua8el5lkIlea-isiE22rk.s,es"SlwyeyScicpgosVthoOle8Ity1rbmo1oeeee-ST1rme7uoso,lnensesauei-faauooonnnffd4di0n0psftt0ohheeeelcvreyebumrmnanaeoos-llrssuteiilSsuo-trsrt3eei3ehedsesenirirs,susitctnrphaaronnogtdtluuocevtitoeossr.. h3FSMpcycooWEdretrts37Niioo90ooll8D0nnyu-5s2t1i1iooS7s,fofe.notaatshhnhpteedsoMelsTpoybpFirtmirOooehboSdreecEuwrruAacc/uttptpCsererWrnmodo,eacd4yyuui0cepn0tto0risssncc.:sccDrirMeebA8s`~al0Tthsy1iheee1se-t2ChcCat4haheaAeerrvm,bebusoasoctwfshvfafiaxinxilngenoiiwtte[yyrhe oSEstEfohuuosscSbcctreeeehoppiltstoohiinneleebpniriiloooicifdftotulcytTthhesctcoctameonyohhlsywaeatadrttroeeosrrrleey,ytapasadoliliipesyllo..myysesrhhisTbTyy.halddilyrrssoolliyynTizsssceerdedeexxappBoseefficcnttgtceehhddeeits saCLLfotoalnnatbustnoooaadrrriaaoarnrtctisdboonerrgmmFyy!ieEctpspahhrrSoleoodccSsseeardcduuruN(tyrreEilee.Saslgs.tiH,eiwwIeiilslp1Nllo3e5lF)ybbll.meei.eorrmrsPooTo.rtdchoeehrdlleoueenacddittessaaatftttesercrylate pecEP(nooo3Tvllniyyt0mrmaoeoe0inrnrnm0mieewnw8nnigattl}aalatilhnllebbdyyeoeesmhrhm:uyyelaldlersrevcicLvialfoayrywinsezteeemdcd.bpplHufefflciiu((sero41rsi-r9sta9o))tcwwhiiLeaastenmnhhdidiigicnhnatttleesmppaeeccrraayttluuarrteee sfTf{(geli2oauo0rroceacrr-nhos4eecc5aad"hn:Cee)mrfEiooscr;reEaaarllnuubgssoehihitsnnyyo.ggdddrrnooettlnlhhLiyyiiocssnnwaiii-lsimslaaogylsppeeeerrtrrcooydusiulScsucahhcetriressoosem.waawewttiiisoollvgsgllehrctaabbppeehhyy,. iiff AoaSa1Eytvvhl4ahaiCaateio-lirolrtleawtaaaibiyeglalsangeeeetae,:,.tsdicooTfarraI"li'tfiussogeoarnnrsWseoaocciellhT1i0ioeiG1qwmgeulebeticrmrrdeaeosclralsicecctsuchhaessuerccilcorsaabmyiiroralnnttaeootwtvsgsehe.aertsileageappthnpahttthryyeh,.i4c-h3 Erhangned, SheSfyxnlEdtauErreosaorplooyclnlshoiaieratmsmtiiaioclornanasltesenrmvaiwaadivreleeelnrdtceoeobnteceeeacssdlttteeiitdmmecaarottmnieiecnintehntldyyhoedenrrasotop:llHyyhssi4igi-shs9 Facer range, pH and rates Buynadceorlynsoirsmalofenfvlivrorooncmheenntiaclalcosncdriytliaotness.: sa c so1E 1-20n =LpeTsoriEty 11 Hydrolysis of fluorochemica/ acrylates: cc B011-24A - Priority II LR 2485-2 - Priority III awrossess 3MA10065543 a N0000058 3M_MN00000098 22657733..00008811 TE -- ------ ~76- AL BPPrhootetoocchhetermiciceaall EDDeeg~ErraadNdaaettailooennal-- TsTchheeevtssauutssecscepetcpoitbiibliliittyy of ppttEi-h'hrn6hee~oeo'sttbopspo-elrr~loymoydosgesfuiuiscstcwestssosshshoooeonnua~ullulddessodiriollbbicieechhciaeacssmhiim ggm-[epsep~lliall;yy,il iccacccaohohcseeartlccytikiklanaenesgtgddessb~tthyychoiitsosncctooaaooatinntininnettghgrhee FCFi((nVooVosmlyylLiplccdoaoooew rrwrseiin'dno),gg,fwiaBasatnuunhdccdshhedeeaaxeexlecpxxpdkpopoosossichisnunoiugrggnrhete,rt,toooslttihsslhsi,eeucurnaipLpliarrigogiognnhddlatguutsccsatfftonoarcccrloooyoouuntnnlltideedacianybybleeeeesratr.. mCm cxaoetm ttchhpaooacsdrtsesadbddlw eeessictchroriiwbbdeeaddWrki aabcbfoloovuvneoet,r,roocffloshoer,rniutthchseaeinlg.aam sasoenunnattlyootfifcal ePEFlelxusutroioaarrctooacstanhhtbeemmleiicccoaeslolltwinaagcMcWrryyflloflarauttoeecrssaorcpaaherceteeimnuugissceeaddaln.daasstaeaxstsiooliiells. In :SrtEEtvoeohhesiisaSissuusnntRuuilaistiineegog,,thnhtttscs,,oaoomcmaaeteatnnigdnooagffs Iitpttfthhohoeeriitssocaacppacchoorrresspyymsselliiitaacbibttnlaleegeless wUatt"inihhsdllaaellttn~sbbtetieehxhteetiieezlxtxteerepersxxoo.ttsriieeflldcoeer dSStyhhheeeaosrfebmlliiuungosghrrtooccahnhaeeecmtniitccaraasallnpsddhfeeoeggtrrroraaciddhnaaegttmiiisooconnal,.lscc"aeaspnpeaaenbbrsllgieeytizooceffor"thefor ZaPpaaorcrcbnororsEpyhyoiollorgsabasaeittetndeedegppttoohhaHllaenlytytdimmoeedvtrrryreasseacd..dntsy~fflFFeeeaooxrxtrrtrteiiislintteeghhibisessfEoiisblrrbeeeeaaaraarrlssssoeoendnncc.,eooarsintgtiItteyedsvyiitsswcowioittarathhllshsseootthhee CccSooaonnnuttdaaiiidnnaeetErrelssu,.ofrleeeucxxohpcroeoosnsaeiec~cetayllttsaooteossssuunndllbeieigsohncsttre,,iableeaaddnnddsinahannoaVavllyeyyczsoeerdd ffoorr low YW fluoroche~icals as described above. PFhroottoollyyseitss ooff fflluuoorroocchheenmiiccaall aaccreyyllaatteess:: AA. O0Locnchn s8E2sii040lt181si15ec-73na2784"Agg~eell-prpPirroiigooirrtiiyttyy1111I1Il1 B. ~. GOcGLconnRF dd8BS2yy04Ieee18Ledd51-s--2322tt0'4eeAYAxx-ttiip-PllereelPPiorroriirffiooiiirtrtbbiyieeytrrtssyyTIaIllI1I1I1 LR 24~5-2 - Priority III E2aFPiiri,oell0doderresoegmrccrahoademdaanmatieticnionadonlneda--ctCroRRyiiRlggsaoeoEtrereooEsuuissfViGhdElelellpcpeododotelessgyscmrmraeaearrdrd.aiiatnztiaaiostoTnniieoosnntttieensosogtftfse tthhee wAifTiinnln1lvuv3looo3lrlavovrbbicieaehnneeggnssmiiibmbsmcuuoiiarrillliilaaaarrllaancttgwwrooiiyttlatthhanhhtaaeelctctsyoormmrreppweedoiocclssoolttmmfiimmonnoreeggcnncddtueeoohrdderr.gsaarffnneooiirrlTcceeasLLmtsmRRaiaetnt33egeo80rrf44ii44aa--ll46 1ultiEanoee0ewsstTtgsoMsaHeWrdssehfnTEnoolauuuutliroisdsroCooiiclcabbhehebeeeanmlncrii~eouccdnnaaallnaffoacordrlkdeyyugzlgaarteatta~atdsellaaseefttsaoiiossroot:unntloohdpnnpereeroogrddryyeuueeelccaaaettrrtass.:ls..ye TohfSSeuucchh The iauisinlsrmTpeleporolrowowoovfnvemmme'ootrnneattiildhhttseeioosorrslsiiaeecnn6bnngg3essliieoototfdfriivviiddbattyeecyyggrrryiaalooaddfafoaatltteossiisucuooccinnhhnwgoubbttylyeef~ssactctdsagasiprpitteeasuuannnrrtdeeiilinnyvwaggoosuulld~ RSRfrEaalalicduduiinoooorroetloolacacanbbhbEaeeeealmlrlaii~ieinccn~cgaagtllaCbcOc2edooteduueegolldgdrrraadbHbbdaeCeyattiaoaiiofcocsnnhohiTlieeCppavvrrteeooisddddneuugrccybbttiyyrssaa..tdiieinnocclnooaorrbnppeooolrrreeaadrttsiinngg eTiattheertner'adBioolylsaebreel.e~ MC or FC acrylate monomers into the polymers. Suatonsssia 3MA10065544 Su_MNoD000CE0 3M_MNO0000099 22557733..00008822 == a -77- ~, ~ A PTdPlooreruwegelrlmMiaiiWmdmiaintnHfaiallroruuynyodrrpoottrcceehhosseedttmnussiicccewwaasiillllllcassnppbbeeeeccbiddieeooensnsceeettthhrttaaeoottidvdaee~acrtsteeeerrfrpvmpoioion.nsns.esesiitbbhiiellffee dsoo2ieiigl"rinaeSsddyya"sstttiteooomnn..deptreTTorhdhmeueiscsnteees ppvrrcehaeIner~timhbnieeinrnarcretyyoterstteeeissovtfteasd fwilf~srlloollrmoraatllhsseoo Cocbhehleenrmueiisicceatad)liatm`otmoiondonoeonmtmeeerrtrsmssinf~(errRooemwmhnett,thheheerssooiilllossssyyseotfteemnfluttohhrreooo-uugchh RHvRiiogglooairrtooiuulsssizasstooeliillonbb~iaioosnddeolagsitrckaeaalddyaa!.~tiioonn tests tests on on cc 2se101-20n =Sparieirity fluorochemical acrylates: cc 8011-24A - Priority 111 ) "efteLcRts 2485-2 - Priority c) "AAPEccofuulfttyeeercetrsfa1i'sashhiobbniieoo,aasssssaaeyypsseraaatrreeednneefeerSdoeendd toohnne tsthhoeelvaeacncrtrysyllaaattneed psSSBsyooouullrlruufyflttaamaiicceootvtrnnaasa.:nnsttassl.soSnwhuwecheh,hiinIccnhhsssseeekkpppReeaoaaerecrtpaaaphtttoiiettdoodhhnneemvafoccruoiooilnunmvdlldeestmmphruupepollrrbssoosaiibbobooaellnnbbvy.lleyooynrtrrsebbmeeoamvmnaeadddee mpBGbbosiiyienoonraoaodasrmriisaeaaairlryyyssisss'ni'aascnonS.nnddupttp1lhhToooeehrwuitsdFdFiiluWnaagmlieolyytltizihihcedogeadedomememexmwcraiaosstsutletedriraainissagapllrwwoeeebllwvvlaloio.:ubdilleddyncSSeuubrbeeecenhmtohvaet Suth2hse8eefuHnflllouunooitrrnooonccsihhuceipmtpiioccraatlsingaScerrtyyhlleaatteeexispptooillnyygmmeerressvidttehhneecmmesseelltvvheeasst Aacruetenonftiosxhicb.ioassays of efalyzed: [cc R301a1-2p08 t~ pariotrity 11 Acute fish bioassays of dialyzed: cc 8011-24A - Priority LR 2485-2 - Priority II 1U.retBhaancekserome i. B a)ackCaoromupnodsition a) UCUUnnocllmeiiptkkoheesaintettishhoeenataaeccrryyhlloaattteepsso,,lyrttehheericffllmuuaootrreoorccihhaeelnmsti;ccaallbut ace ZutfSForrllirieuunamtoreethroriaoscsnnc,h,eehessenmttiiHeeaccyrttaaearcllaramrcneecaaorrailtsaccc,,hoophnoooonololifrysssm,,ioeoctrtoihhddncseiiorriilssmsoomsa.cmctaayeyilarallninFaaraltetoosielel,esisisgoombaarmounneedtldrresscaureoloffes oe Seen the Tange of one sometimes hydrocarbon alcohols. weights are in the range of one ttToo~ettiwvroo mtEohnlooeuscssauannldsa.:r 5b)) PPhhyyssiiccaall pPrrooppeerrttiieess H TpIFhhrreeoeppeeEea rrnnttvviiiiesrzssoot nnmm~eeafantntattasalloonnLLaatthhbteeooerrlpafttlS ooulurrosyyrtoochhuhaahseesrmiiL nnccooaallpphhyyJusesreiiecctcaahhllaaTnnYeess.. These materials have low water solubility, hut net soph, In Ble me a their solubility in lipid materials is xipnecntead HtoEhiLve' LlovEvOaratS iiity. E re unknown {126). Based on their F~, they are expected to hawe low volatility. Mat0ss845 3MA10065545 aW_uN0000100 3M_MN00000100 22557733..00008833 -78- OF regataion ee aa c) Degradation ..... T The fluorochemical u~ethanes are more stable than imely their hydrocarbon analogs, but they are less stable than the fluorochemical acrylates. These materials are more likely than the acrylates to degrade through hydrolsis; photolysis, or biochemical mechanisms, releasing low MW fluor0- chemical monomers to the environment. d) Effects rE a Environmental effects data on these products are shown in Table 13. Like the acrylates, the .fluorochemical urethanes are sold in mixtures FEA TN "with other materials, including solvents, surfactants, and polymers that can mask the toxiciLy of the urethane. The tabZe shows, however, that some of these products have hlgh nn RL ee nn concentrations of fluorochemlcal urethane and little toxicity. These data indicate that at least two of the three uret~anes are at worst practically nontoxic assuming no antagonistic + tecmmntet utine effects on toxicity from other product components. 2. Recommended Testinq a) Physical Properties ~he possibility o bioconcentratJon of urethane products should be further investigated. One possibility is that their molecular size may limit their capacity to bioconcentrate. Further literature study is needed on the effects of molecular size or molecular weiqht on the bioconcentration potential of fluorochemicals. Most SAP methods predict bioconcentration from octanol/water partition coefficient. It is Se prin ce LL recommende that the octanol/water partition coefficient of the EtFOSE/TDI urethane be ~etermlned as a representative of this group of firm RRL OL fluorochemicals. The most appropriate method of making th~s measurement appears to be the use of reverse-phase high-pressure liquid chromatograph (136). This method will prevent possible interference from other components of the product mixture. The T~I component of the molecule shoul~ facilitate ~V eetection. n-Octanol/water partlt~on coefficient of: 2 EtFOS/TD~ - Priority ~II frm 3MA10065546 pp 3M_MN00000101 22557733..00008844 EEE ES mn srmragr mz 33 L ANTE TCT TAT ON RETNA PORTS prot vet.n B4 emtna Prtuces containing SecsE/ cmon ws ce woes ns coon cc 806-6 ea10.5 ccec s80e1r01-s30 `6.2 =cc mer 803-15 54 come cc 811-17 m9 Omermla cPCrd8o1n1t-s18containing20F{9T8%SofEsolids) . l~u~t$ 5 containing Ft~E/TDI wns c~ 803-3 i15 wma oo 782-5 o1u5 rcco7v9e5-s19convaininy142 ere coy masz x Prc~ucts containing 2 Et~E/cDAb/pAPI LR 2485-2 10 wu815s-1 15 conan 3 cc 8110-938 30 SasE OF cc 8110-96B 30 pte s cc 812-35 5 cwsn os cc 8~5-24 15 9s6e-Hera.. 105 0180 2179c ie1~,0e m233 PA575 oon >10o0 "w440 mma >2~00 s1e02 56 65 0400 2%1250 m131 339c i2e%284. Po1148 fe:1306 a6S9 =527 apPrestiter Lab ~guest Number or {Reerence) am[130) sms5785 a6363 ss5546 "on6671 wn6672 5s49o3 ae s43o6s9 5055 sa2485 fd1204 azm(129) su5511 Ey5983 oe6814 amI132) nomen: Footnotes : 2 ALL data on Futhest iors lens others mts. All data on Fathead ~tnnc~s Saat OPA = Stearyl alcohol. Rainbow trout. & Bh Tntien, ~lueg,ili sunfish. EEL Da~ni~a manna, 4R-Hr. ~50 unless othe~a~_=e noted. ar0085547 3MA10065547 Sunosco0102 3M_MN00000102 22557733..00008855 a0 b) Degradation -80- AL b) Degradation TTFeeosscttossnsassniidnmeitdllaarrto ttcoohettchhkoosseseusffcooerrptttihhbeeilaaicctrryyylloaaftteesstheaarree pVuBurhirhreoteoechttttoohohmdadamtenenehgeseneredaaepapdddcrraaroottyddtiiluouooaccntnttc,e,sshse,caattknnooddhsbybuciidcshoorhceddeomeeemlipgigyccrrtsaaaaiillddbsaaittlhhtiiiyyeootddsnnryrt,,osolloyywssiiiltsslh..e beAAssFun wowSSSniiin1ltl'1ilhttchhaeehbteehepgperrdGlooooaddnncueuaerccnytedlooanntoaaesnsttshh,esedsooyllepphdddrry..oodtddreuuoxcPPcltthhytiosolittrresooeeddssesfiitggdaderubruseareatdisdcasllsttwee.iiiffottlonlnoonnbtteeessttrssun sBBFeiiislosiiddcceeuaggerriagcdeilaanttiisaoonanndidoTtneessttdssyedwwiilltllextbbieeleddoonnfeeabrooinncstt.hh.ee pprroodduuccte residue in soil. cIIett 8ti1ss1-rr1ee8cc.oommmmeTenhniddseeddprttohhdaatutcttteesscttoiinnntggainbbsee dc2oo0nneesooolnnids, and cz93ca88%4ma8oio1fnf1-i1ntt8ghh.eeii3rr4Thssi~cooslliiHddCpssrLodaeaurnrceeutlsEEic~LfFoFiOnOeStSzEaE,//iMNnDDs&II..20%TThhseeolids, and SFrfulelrumufoaoarirconotcicahnhneegtmnii2ccc%oaaullilsdssuuMrrCcffLaauacsceettmaaunnslttos,.imfeiecTTrohh,neetuppasrriee3ossMneennccieen ooff tthhiiss dsduiiauernngrgettrfrteeaaahrrdcdappatnarrtaeteesniitttooiinnnnwggocouoocculrrccldeeuudssrruus..llcittamssupsTlTehihiiefeffysuuooossnmaneeleln'yyaloocffyvvoteenirrfrrycyuaaasddliiillooooonllwwwaoarbbillkeeneellvveeeaeddlnlsds ooff ppurrreeevvteehnnattnesssuuccwhhoulccdoonnffsuuissmiipoolnni..fy analytical work and DcDeeeggrralaaiddaaTtteiioonnTecttreeosssttssmooonnn)fF:lluuoorroocchheemmiiccaall uurreetthhaannee cc 811-18 (EtFOSE/MDI): RHHRP~iyyRggddOoorrtrrooooollduuyyessssgiiessassodoiia--lltiPPobrbrnliiioooorrddoiienettggyyrrsaaidldIIaiIarcttaiioongnel-= P=PrriiP. oorrriiiottryyityIIITIXIIT PPPhhhooo~totoddoeedggreraaqddrraaitatoiiidroooainnneyooonnniSsdfyiyeledid.c.affaabbgrerliicc--- Priority III Priority III c) eEtfefeeccttss AEAllltithohozouougcghhhennnioocabbliiooaaussrssaaatyyhsasnehhaavvseeionbbsee,eennbiddcoosnnesesaooynns ttohhnee the EEfffthhhool6eerrunmouurwwUllooorrarcaessthtttteehedamdniccecaapp.sasrreleooddououuSccrcruttcesshtllhooawwcpcneeaarsesnnettdiaaalpclplootlolnsiosoeswosw,inisbsballbeeiddasoeettsattouoseemxxsrreiaimmcvciisiinntttaahyytaottiniododnuuntaseihleooffttoo ctEthhrheeeemittucooraxxeliit,chcaiinttaeyyn.dooffaSiuttochheheapppgrrsrooueddmdeuuiccctttniooiinsstsoxdGuaieescsiutttmoyoeotthrhteehatfflluauololrrooCaaCccnnoonhvmmtteippmaazooiggonncoeneeannnnlniite,tsssnset..iiiaascnldsUeUsfdsaiffailnteansgagccotesssatthshhoiisffswsurrsmooenmtteetccoohnhhttaonnthhiieetqqrroEuuxLeeppiF,,rrcOooiSddtpEpuuy/rrccMeettDssoIsernnttand oeEBEBnuntuEltvtFFyiOO'rsSSsoiEEitnm//momiOOieDllDsnAaaAat/rr/yaPPlAdAdtPaPahIttTadaatatuuaororinneettstshhhESaaotLSnnwFP6seeO-OsshSSrEEt.//hhhTTaaaDDtvvfIIeeisEhuutllrrFiieeOLttttiStthhlsElaaee/ennMgeD5ttssI1oo5xxiiaaamcclnliildlattooiyyww.. uuss o((CnLlIlReRys's4#55t04ot59o33xs))ia".y) tI1tht0sahta8nL1Ci5tt50shis9ii:ss6-phprrr"T.ooobbaacfbboillmsyyhplemLmutuCcceShh0 thhR>ei1i5gghhdemeargtr/al bST(aaolssueeaes,:slsbS~iiooofox~aacsst)sahaaiyystsshauanarcreeettnhainnnseee.ee.ddeeddToccoonnc7opp5mrr1poo3ld-d~u2ut5cc~ttssi~sheiwioctndhehaahhiigghh levels of this uretnane, cc 7512~25 is one 3MMATA010006655554488 3SMM__MMNNOO0D00O0D0110033. 22557733..00008866 ote oh SIAL pcEpEooloosnlsnsosttiriaaobbiicllnnheeseanp2p2ir0r0c%ooaddluuEScct-ettc~8roO1omS-sffpEeooo//rrnTreDouunIlsstee."aaxsiinnAi1sst5uusssccahhmonnplllttyyseessttofiinnggthessiinnccee it GGud[freruelameeumtotnoohsnhrnaisaontttncsierhe.anaettmaseeilicooanniTlestessUcwoppoosirmutoopldbobda,aneDbbnileetee.esvvTleaeacennAkk sbhoaoeeffmtcpttlsSeoeirirggnnottoifioffiitcchaaenntt ~9o6-xHiec.ltyP.ian Lcsor 96-StE.eroFsies/htoLrC50-= priorisy I EtFOSE/TD[ - Prioriy #. p FLUGRuELeo sanngdnKKeELvs -rFee si Pooilvysmeeecrss 1. ssckazouns I. TFRTmBoheoharreexcaessakeetgoourofppofurrrtnotoohddhpdeeurucoctffpesooa1lnllaaeoozr,ovweiinnhahggniidgghhmmoocnnMhWoolWHmmoeerpperoooesllos=yyrmmeerbrvvrssiionntymmyollaariiddddeeteernneiEfe.fxrlooufmmclleuuooo-snnrteeiidgooeerr,. ihebBEteehrehxiyehynaoleglloe1unnufTbeeouuirlreoltpyBSyroononmocuptemuravreneoaadedtll:,,asscooatitihhnhhnaadee,vvsseeeec`haplpcchooouuallrrryyaobamtm-etieeoisvrrvrresseembsayserryttoeeseymtoae-nfnsmnotosemnr..rtiicoof:xxliiuAAceoff,,rtt-eerr insolT8FFFuS0lLLbT1uUUl0OaOOeLSzRR,liTEEldILLAeReOn--oFnhFh(avaLL0seoUU.lOO4a3RsRbtEeEeieLeLmlnngSe/,aBfBf)rooruauaannnnnadddddndetvfooxlsltmuuaroeollererslamcoceeeehlllaayamsosssuttmminaaoontllemmlslreetrr.aoafmmcccoooCuunnottpss ooff dBEuf((ennl05r2ddu.2aeo738rgrr45ri1dam0dSegniH05/fT01gfo(e7)4ef0cr.ee4Sc((onnp3oL2attaamnb8g9cc/1oforgon0nedu)d-dqqni1iuudtIteaaisiAsntotodeonn(ssb351se233m771alI030leso:))laax..ccihhaceeTmddh"oA8outnol0T0t.a:aLs2t3etfn6e6eicrrsohmmhfapgssttaCtsun.uoOofddd8Dyyf/CrcOooDm0 pdSIcaeScaorpmnh8ming0inir1oudan0tsm:-o1s1o((,fA13Twcn7cao,s1E3t88o0f)x1oE,i0ucn-d1Rbn1utaAtcooEa(rfb1ite3Tse7)lrtN.oxlcEieucaTrhciSenhtS9eodlS aeftaics(h1h33aT 50t0a)e.nFd ffrcooorrm TTp1eoo5rxxiiimoccisiinsttu,ytyesvw,aa"Css2 naao6ll0ss1too0o-x1nin1oco6tt,mffaoo`tauuennnrddiiadalaeffntttleeierrcaacllhloeoFndnLggOeo(rOr1R3E8cc)Luu.Srriinngg npafEelldrulcEioouotrtrtdhooaseeta,liieavaTsesottcpoocsaimnyteees8trrit0,,ee1nm0,,-eae1xxs1ccelBeeeb,ppancttocnrhaeentcddhhcaaiottoodtnneellniiyytttitcddo.0aoa01le1sss1m2m~p8gLnnoUovtOoo.orRffEcc5oCCoenOnODtt/Baagii,,nn mSShadcSonaaaauUdnnp~ErmoohAhacmTmnnttaeIieiihirVvedravEsessselsosoeTa(,fryay1Isec3tnaTh8tteher)ah"enm.ete',,e fthallTawTennaouhhddsoeoecrs~saeannontouoscortkshthreeeeesrmrsrttieoeuoizfcrslxeeaiitillsodsctuuhaaeppt(llooonalltdlyyoffifcmmxilciaeeissaucrrhctooesseirrtoooyccrtthhhheaaafmmttriioccmttaahhllee nerd FEhoRELs Flusroetestomera. themselves, are the cause of the toxicity uncured FLUOREL fluoroelastomers. from KKSeellE--~RF -~KeNNlooleegnnvvpiiorlroyomnnemmreesnn.ttaall ttaessttiinngg hhaass bbeeeenn ddoonnee 2. RecomonsuntdheesKeTle-sYtinpgolymers. 2. RNHTooeucoaemnnnvvmieierrnoodnneesmdneennTtteKaasllteinitt@eesspttiiannlggmaiitsse!rreeccoommsmeennddeadd for for the the FLOORLe and Kel-Fe polymers. awic0sssio 3MA10065549 aw_uoooo01o4 3M_MN00000104 22557733..00008877 -82- IMCOn Ar I catalysts <P * Stine i. Background iP INLE B yyr---- 3~ makes two hexaElucrophosphste salts which are used eene ma mht gt as catalysts for the curing of epoxy resins. At th~s ti~e, these are used in low volume products (cc 792-8 and cc 794-6) and their prospect for significantly increased volume do not seem great. 1 reggrenaations to facts hese products in tne 2. Recommended Testing No recommendations to include these Products in the Part II Fate of Fluorochemlcals program are made ~ thi~ time. 22557733..00008888 fr-- 3MA10065550 3M_MN00000105 6 ay -B3- Vv. sumary ENTIAL SUmmARY AASSavreeasseuru'mgrTetimvihaaeeecrnnyyprooGinofnfpoRpTpsrraRoeobcppRleootsshee1Tedd4Es.etteeTs"sattaRoiibnEcnlgNegswwt1Ui5usitdthhyp Berpe tppeardrriiiiioccootrtrdssii.ttyycToorrrisantatnsankktiihppnneeeggsrreaq qannutuddaaabrrltcctee eoossrrs,tt opcPEErrEerviieiiettuooriilrrcctiithaasttellii.seefssproronTTarpaaanobbntgsllgheeeeeed ffI1farrthtooiiremmnneeot1Itf-hhyeeffeooParrliiunnr vottverrresrooortuyddcyduuhycceiitemnmiiipppoocooennerrrlttiogesagdninitvtv,peerssttoooIgnasrIIasIstihrIuuemmsmmFffeaaaoorrcrrytytallbooeeI:fsslesss, SrSfrEeuleilpmsuunomuooaralrcctrtooi.sicceehhsseafmnroioioffcmcaoleletsnsnhvveiiaarrrrFooeeanntmmeffeeoonnuouttnfnaaddllF~l1ndnduaaottoorasttohhcooeehnnrremittttchhaaeeabblllseevvssaarpcirittooohhusgrrssrooauumggcc,hlhioaosusuePtstsaeerssttthheeooIff. 3InM report. TgT330hah48"eep5essftteieiennsscttiitttnnhhsggee OrbrpErreeaeccssooIeemmnnnmstteeFnnldduuueeonnddcddoeecrriihnnssettnaattinnhhcddiiaisislnnsggrr.eepoopfoforrEttnttvhheieiicssoeennniinvnvnettiineerrcnnooaddnnleemmddeennpttrttaaooollfiffliifflelaallsttee LSSdLaFeaneadvbvbeoeuolrslreeoaofaptpfteeoeoacdrdrntyydsffdrtrtiooooosfmnpggoii3ttsvvMhhaeeeelssFeelrrueeioccnssroosttommtuucmrmddheueiienecnemdstdsiaiactotwwainiiilosollsnlnl.ssteehnnffaotaaoErbrbnlwlveieipFlrrrlooattndghhumuesececittnrEEtinnanmnvvlooiiidzdrrieioopffnnriimmopcceefoaannisttttlsiiaaeiololsbnnlsse oiSernnhdvviuirsaoeocnncmmuaeernnnadtttaaedll~srpeeeoifssffpaeeolccnttsssei..ntsotTTrhhuteechsseteeioeppnnrrsuooiffttiiohllmaeemtssenwtiwwaliillllllcmaoialnlnssciooemrinzeesennaabbpollfoeessirtbaalppeiidd GgaoonvdveerranncmmceeunnrttatesaggeernneccsiipeeossnseaannddtoI3Mtheccuusestntovomimererorsns.mental concerns of AhAlfnanlutuSeeorxpxroaraocmmochppphelloeneemniieccooaaffllassaa rhuhcraaleessegg.,uulleaxaiinntetomoprrfftyaayiccttnpp,,grroorcbrbeelelrcecetememannittccnllaayyuuscseelssddauusrrsffbbeaayycsceellddoaa.:cfckkpToToohfhfleeynddeUaaUrttSSsaEaEPZAoonn hhfhfFooairrwswoloeemnovvrpeearpPrrcohM,,hpnNeorsaarriertaeca~eqqauuliianrzrooetteprnmoueelliinnyennttmcceselle..ruuxsddeeemddapFrtFleiluiinynnoogprrrittionhchnibeieessa-r-bctcolaesonyxixnetnetnasmapsipcirntnliiieiaoonnnsnngg.vs.'eisrppoooilWnhoyyhrfiemieleelnperretossal.,l3ydlMumyerssafe aSafshltvuhiotrhreceoncrphpeoeolnmlyiiyracmelaerlrss"daptoiialnnyclmtloeoudrdssesddubarsiietnnanpttthrhieeoabtaeeebxxelemmytpphttiaiissoonnve;,inevwwvipeerooinilnmaatceckkntoandllyhenscafee Cceaannnvnnieorltonmpperrneetssassl ttdhheaetaaaggeetnnoccyysufbfoosrrtanmrtoeidsaiitffeiiccaat~htiiisuonnviooffewpttohhieentfreesagnuudllsatthiieoonnnc..e uPufPnrnrldedaievevrririoossocututhsasaennnsdttiiieecnnssaggtttiisnnoo,ggff bhhttaoahhstsee oaaeannlnllvlvlyioiorwrweooeLdnndinmseeittnnthhtteeeaadllffooirpprnmrrmfaooaotpptrieemioraornttntiiioeoeonfsfs aoaoiffsbbaaa3IssvMniiaccilable on tttttfhhohhleeeexuiiiiiorrrrcriovtcvlJoyhooolelnnamaggitlt--nicittflaleeoil~rrrtstmnmy,ya,,tssittboaaussnbtbooiilllluouiiibnbsttiilyyllya..iiittslyyoi;,mIininltettessshhdsooeemmiieerrcionmcnscfaaopoossvlvreeeemessmtan,,eteeinnoteettnnnhvvaiiininnirrsoosdsnneooammsiiveelilannrittalaaabaannlllbddel.e on toxicity information is also less complete than desirable. SsFFtEthllaaeuuRlboorIirrTlsoeiiccnthhtvyeeyinmziioooccffanallrttehhnpeeptirirarrooldduupPcceepttrrrssfoflpleuuaarorortereeiiiennsssaouuttssepepideses,ccttpFootrrbhbtteeeiicccooaeannufusssce..eree,ooffKKnnvoeottwrhwheyelleedaeeiggxxaeettprroeeroommtffeeant tittihnhhhnaaae`tttioorrradga3reMeveerrnvtfiltltLroovunooopnmmrormiciooesnncciniihhstmenelaimmilezi~zecceaaopllrrttssohhpeeeexaarcerrcteehrhiaeaenrncCsccaaaeeluusssysiiis,nnocoggFfostteehFflnneiiyvvrnniieddtfriifoononorgngne,:nmu,eennndiittonvna.aellrttyhheepprrioomffbbuopllttoeueorrnrmteetsa,.nt that are impossible or extremely costly to undO. 22557733..00008899 3uMatA01000868585S511 3aMW__WMNNo0o0000000110068 -- JE J 2pz. I pte mmm ps 21 0 Cts 1 pmticiionnof stiating 2 eFonew ai to ro sostes a1 30 Erte 3 contin spin ett bing 2 rite spinga suits geen 2 onnionts A LAr ---- EriEtRy seTfRp=Eoanr Cost rw na 650 29,25 x ame ss 1,300 58,50 rw on 150 6,75; rw " 20 90~ a am seco ,200 54,001 wom 2 200 9,00( -- Footnotes: (2) Coieof rts te shun in eg 7 (a) Chemistry of Products is shown in Appendix II 5 rm Sn (b) 5~R = Structure Activity Relationships Be [c) ~y Foamer 22557733..00009900 sunasiz 3MA10065552 sumo 3M_MN00000107 ---------------- ste 14 (contin) Table ).4 (continoed) rvatnox: rGPerooadrucectty sical practic 2 Seirlay sNroEsgRpaStes Alcohols 2 2) ndnpS~-csOoctcrrttniaabiniouot]rcin-aoWntateerr TEE coefficient a) Shaking smtecms Surfac~ants Fr seARfslcgopEheaoltses 2 sb)o sorption 3) a3 k Soil Sorption PPoRhsoEsaphtaetess 5) RmSPohuemorpsfpamahccattaeenssts Alcohols 14)) pVaoporr pPrreessssuurree SSutrafaccatna~ttss TTo~eossgphhaatteess Alcohols 5 bstoption Swtactans 5) Bio~orption Surfactants pm i~egradation Daetine I) Alkaline raeelysis Hydrolysis Nsbols Alcohols J-- Acrylates J Urethane 5 pone) product(a) ANE: " 3M "CONFIDENTIAL Priceity ReTTgT~Tepisisimtntceiieennmggents Gwe Priority of Work mT Requirement~ ges Cost LCaSD ~cmh7398ea54a -4ns2-34 mI1IIInl 5338<05 pii2L,,eo25E57dm(: L~ 4197-2 III 5~ 2,25( een 1 = 12 EKI 80021 I 25 mast 5 aE L~ 5625 I 25 3 " ak cc 795-23 I 40 So 5 pS LR 3844-4 I 25 Fem in 2 TEE 2 Et~DSE/~DI III 25 1,12.~ 1,121 1,80( i, 12-~ 1,12 ePcES acelm7a9850sE n-02231 HooIInIIml 91x%i0 5 o4,s08a657e~5 a SR LLc~Rc. a537869a, E42545-d-243 I0mIIIoI III a1113x555 675 =675 a=675 SE[mLo A2RIwe54861e02950ne 7n2-12 mIIIooIlImmIl 1111ii555 oa9666777es55 BShaina cc 795-23 I~3844-4 xkIIhII 15i155 Ga6677e55 DmELAPauI4s1s890te70-2n21 mEIIIIHmI 11ii55 66aa77s55 LR 5625 IIl 15 675 LLSwB~Ploa34S1iwa4947dsd--42e u1IIooIImmII i04400 11bLi,,i88oi00]0C SZouesmt cc 8011-24A L~ 2485-2 oFII III &6600 i me 2,700 2,700 cc 811-18 II 60 2,700 22657733..00009011 awatoosses 3MA10065553 a02000108 3M_MN00000108 Table 14 (entire) Table 14 {eontinue4) sTseesitreomxent Measurement Cpartoedguocr:y 22)) pSPrhooottnsoliyySsalitissce a] o~ Silica Pfoabnridcs fabrics c) ssiennnvssaiittteiirzzee~ in water SSu~eta octcan~ts Aacalrlccyoolhhaootllses .s Acrylates uUrreetthhaanneess aAccrryyllaatteess UUrreetthhaarneess. Sus~uftaaccttaannttss 33) BBiico~deeggrraaddaattiioonn 2 Acsiisstes SSuurxftaaccttaannttss sonhii Suctactants bc))RFePSh,Rroiieecigsgsrlopaaprieiorr.ruo~cm~eertrryy Surfactants SSuurcftaaccttaannttss Aerobic RFAPlrlhcocoosOsrphpahohlalascsteess AAecrryyllaatteess DD)) ARRniisggeoorrrooonuuissc trSeutrhfaacnteasnts SKulrefcahcotlsants 44) EBa))iiooAttPpFnrrlllaaaaaaennnnnrstesssoftbooirmcmmaattiioonnAnAlt!cccaooo~bhnooorlls b) Fish Alcohol BBiioocsoonncceennttrzaattiioonn a2) Fr~iesnh sSuurrtfaaccttaannttss . h) CCoonnfitrim eexx-e AAllceochtooll traction ~th~f eEftfeecrtss I2)) s96e-tHer,. FFiisshh TTto~x.. SSuucrtfaaccttaannttss -86- 3 CCFDENTIAL Promiee) PPorrfiivooerreiirttyy of ~.brk Requti~eTrTiseiitmmrnieeennggts (hes Requirements (~rs L cCooustt t(.t~ mEiAeIes8ew0x0en21 ImoImI 110000 LR5S6e25ed III 1io0o 4a i a4,,s550Oa(C LcddcLccCRR23io8848m1084oz1L44-I--se1-e24824A IoaIIImmIIIImIlII 1l1i1l1o0o000o0p80 4pa4445,,,,s5555y%0000x[E[( mccCca8se01os1-ns24gA cLR E24u85w-2 oIImmaIIxnmIl 01111000000 asx 4,50C odcs 4,50[ CC 811-18 III i00 4 m oELAo~5I5sw86e022we 05s21e mmImt 1101i00oo0oo 4aw4,,5ss5s0a0cCC CC 805-IOSc IIl IOO 4,50t scc m777s-3 oIt 2=O 090O epDraousdquhctitesrsTe. I1T Fcced8.05-TIe0Sc IIXm FE2=]5 320 11,1022c5 Lia LPmsGF~A~srIR5.ee68e20se50In2.nD1. o.IIIoImIIfmI @i25 45 45 p212zo,,,ro010z222:m555 DcLLch~~cnoas347819nes495a47-ae--2d423n 1mIIIIIIIml 45 i45 &i45 22o2,,a00022t55 22,0025 ccIcLcc~n as882ae140iea181-s5s1n1--:8224A amIImnI ImIrI 45 45 pH845 22o2,,a00022t255 22,0225 a LR 5625 12 3844-4 IIIn bs45 45 202s 2,025 2,025 Lw oR m38a44e-4kaImIm EF050 2v2.,i2255z00 LR 3844-4 III 25 1,125 mEAIrs8ea0es021 11 s5s=5 2p2,.4d0785 5525 55 2,475 LaP e3844s-4 3 = 25 1L,a12z5 ceTcc29e802s59-t10owSsicen m1i1x1 l1o LSP&oww2lii9vtt2ehh9roo)uu(rtwiL5 IIl 2O solvent) sP45oo0 9O0 watoossss 3MA10065554 U_MN000010 3M_MNO0000109 22557733..00009922 I ble 14 (continues) ~able 14 m~esaitt mootee Mea~u~nt produce P~x~uct foe Cat~ory p-- Acrylate oUxreethnane 2D) i14e-Dtay ANlsgaee Susrufahcotuanntss 2 nla SPhotsossehlar~ttneesss 3) 28-Day Daphnia Surfactants imFo=hsoipspanhcateess Alcohol oa) priority Total Priority I al ortey 11 Total I~iorlty II ol Felony tin Total Priority III oTottaall PPrrootjeecctt - SMCCEIIne Frioeity BemriieTrseee~minntss mw) Gen Priority of ~rk mm Requtrenents (Hrs) Diam Dialyzed oCme cc 8011-24A I3I n =25 2 mR Dialyze~ LR 2485-2 IonI 025. Et~DSE/TDI II WEB 1 LR 2929 II aSmy e n cc 773-5~ II 3331=355O cc 777-3 Swf c~ 805-IOSc SDamma cc 795-23 IIImo0mIIZn 3=3333555 nLLccRRsEcm752h796si3s22-e955se8 1II II II 25~ 50 50 PSccSc~a78yr70w75-i-3IsOS IInoInnI i55P5o0l0 Bes cc 795-23 LR 3844-4 IInIXm 550 50 2121,,8121s84050 3,465 9 6,890 Ccoessts (: az 1i,12 Pei, 12: 45~ Le 1,57f eida 1,57E 1,57~ LE 1,57f va5m 1,575 i iE 2,25t 2,250 2i222i,,,3.2225m55520000 Im 2,250 2,250 115055211,.,s8833200500 155,925 331100,,005500 22557733..00009933 Wr0ss585 3MA10065555 awoa0no 3M_MN0~)000110 ee ne 15 I TABLE 15 satu or ness vo SCHEDULE OP PROPOSED D.~O~K aL This table prioritlzes work and schedules it by quarter following program approval. The schedule assumes a l-i 1/2 man rate of expenditure and availability of the radiolabeled materials listed in Appendix III. omimom=S--n-eey sFToitRLes-- rEImEe-- SEsRt mam I Field : SB REm E--S R--E--T = I mesm TE oSeme. s 3 I : rCoEmRpEsS I : +SHeEEcRwEEt e3y I mena pEeRTan sue I ~ioo~adation memeemus - E r-- mommayermthpeeoyrers =pBorE ~ioconcentration Confirm analytical capab~!- ities for TOF, EAI 80021, LR 5625, an~ LR 3844-4 in spiked soil, sediment, sludge, tlss~e water samples. 150 l~ictive~o~ellng for field stuck. 20 Water solubility of c~ 795-23 35 n-~ct~nol/water distribution coefficient of AI 80021, i~ 5625, cc 795-23, an~ LR 3844-~, 115 vapor pressure of LR 3844-4 15 Acc/imate~ see~ BOD or Shake fla~k st,~y on cc 777-3 (save p~ucts ) 2O Time quarter 1 Cost quarter i - 530 hrs. $23,850 sts 3MA10065556 wns 3M_M NO0000111 22557733..00009944 I soar ures ty ce : om u rise FR T Bomemmim sour 1, quitery FEYear i, Ouarter 3 x rueField x J I Bio~e~ra~ation soar 1, quer s FEYear i, Quarter 4 = ree Pield HM Psi ppurties II, III Physical FEII Effects -- 2M .-.\ -' :C--0- TTTam.I-rN.,aTNITAIALL" sesctpnton sie tne. Time in hrs. ar SSS. a125 = SSeigniec1-- a spi-- ng wn Identify bio~egradatioo fm 3 ~-~:~ucts o~ cc 777-3 - Hen boconmtration stotes ~ish bi~ntration studies SRST we cn FA~ 80021 and LR 5625 -- 30 1s Time quarter 2 Lm 2m Cost quarter 2 - 300 110 560 hrs. $25,200 reir styon ndoien Continue study on ex~stirg SRLS. is SA~applicability. 125 = Cone ella spi and Continue field s~p!ing and pio 2 analysis. 300 - igure aerobic on Eag iz, RigOrOus aerobic on EAT 80021, EPI ET Ph LR 5625, L~ 3844-4, & LR 4197-2.180 icart 3 + ats. Time quarter 3 mam Sh Cost quarter 3 - 605 h~s. $27,225 = conte st tii, Continue SA~ applicability 125 mine tiett saptivg 300 Continue field samplin9 30O Foy and analysls - someloflBAL OL, 565 Soil TiC of EAI 80021, LR 5625. kathy bing Cc 795-23, LR3844-4, FAyitd and LR 4197-2 ot sige 18 200, oe Ts 14-day algae L~ 2929, ~: 773-58 Smee Pp. Solids, ar~ cc 777-3 105 Rp -- 9G-hr. LC50 fish on dialyzed foe A acrylate polyers cc 8011-24A, and Ei LR 2485-2 50 -- ee Time quarter 4 mami Es Cost quarter 4 - 655 hrs. $29,475 antcoesss? 3MA10065557 sumcsoortz 3M_MN00000112 22557733..00009955 YYeeaarr 22,, (~uaarttearr 1I peiortty Cateoory 1Priority 2Categor7 3 II riFieelsd IMI Bwsical properties II, III I~ical l~operties a EEetftfeeccwttss Year Year 22,. QOuuiaretteerr 2 2 m oSAe~ TIIo, II peseadatien Degradation un II PY prec II Effects Year 2, cwrter 3 mYear 2, o Ouarter 3 III SAR nr ysical Properties !II Physical ~rties moan II, III Peitce~segartaa~tatiioonn Ed 2ah ogLina -'-: \~,, Description Description TTiimree tino hhress.. -- rFiinniisshh ~ 0 asppppllilceambiiiltittyy 112255 ~-amFFiiinniigsaahh sfi1e6l1d8 ssaarmap>lliinngg aann~d F analysis 300 -- VVaappooSrrerpp,rreecssossuumrreeeoodff,EEAAIT 2D800R0022A11,,I2 G0 LR 5625, cc 795-23. & LR 4197-2 60 =- w1M4t-e~aayy aaBldgEgaoEee ccco 8a005s--I100S8 an4 cc 795-23 70 - w28-nday Daphnia 1X 5625 10 an~ L8 2929 100 GTToiisrmtee gqquuuaaarrrttteeerrr 555 =+- 66255,554he7rs5s.. Cost ~arter 5 - $29,475 ---------- -- toStaracrttErittnoocaddceuhrreiinvvieecannteesww ~ 57 00 for f]uorc~hemicals 300 --fArCALeDerkpipararleleisiecennaneenttanhatyytlaoi%r~~ooollaysycssciricsysylloaootffteess aanndt 1 u~thanes 180 -~ bBilinoopttlrraaannntasstfoomrmmeattiioonn ooff 2LP 33884444--44 Py in plants 50 ~ S2285i--ddsaa,yyDcaapphintiaa oonn cCccces7773r3--5o588ss 150 solids, cc 777-3, & cc 805-I0S 150 TiCiorsmete qqquuuaaarrrttteeerrr 66 =- 603800.6hh0re0ss.. Cost quarter 6 - ;$30,600 --SeCCooinncttiianntuueesnneeww SSAARR ffoorr fflluuosrroo-- ES ~ V~caah;sateitemecirrcaasslloosllsuiubcisolinieltlyiostofyf13ff3llu0uO4or1rO4o- ad 25O Fae chemical alcohols LR 4197-2 L~ 3844-4 an~ 10 - SfSEEooooialSulmlreerrrreewCssipitpiehirroppmorreonotdderiutoyecssotnyniihdheleya~ndmrtreoioi~frEyiylceaa- " tion 45 WaT0085558 3MA10065558 _3MM_NMONXOO00D01011133 22557733..00009966 rPriiotriyt7 wII,oImII mIII u II CCaotteegoorry7 Ettects Effects tone 2, Queeer 4 mYear 2, P 0uarter 4 III SAR mIII IInncciinneerraattiioonn m Siesucrption II I B ioadsorption DDeesqeraatdaattiioonn sess 3, uaeser 1 mYear 3, = Quarter III m Pysten)poperties III Physical Properties m Desratarion III mm Ettecss Effects - spe mescciption # -+TioreIiNn ThesI.AL - BRI iiggoorroouuE ss aanraaeerrE ocbhiicc bbE iicc~deegsreaadtaaT--ime in hrs. - BbthiiiccottnErraaonrfssftLooRrmmm5au6t2t5ii,oonnLooRff3L18R344-364844i4--44 - 22in8d-f4EirasyhDmaeRpehnniiaa ~cco 79955-233 25 w iEaTnin~meeR1qq2uAua3ar8ttN4ee4r-r477 -+ 618 i1000 0 heres.. COst quarter 7 - $27,450 ~ SCCoommntitiinotuuensnneewv ~ a8 ofoxr rfluoozo- = =EfhLcyhoeekcEmiicfuaoclirsetesoxniiinncetA~eacrtaotecurrheIcnniciciannl- 250 x bF-~ - SseDS oiuerecrtatffeteiaronecmriitiI naanenneemetisssaastdSEissR AoooH~nrmsppO8te0iiR0oo2nEn1ooafafnedd L2R 55622550 - sEESstiueeomrnmEffsaiaakctEccttittiioaazvenneatt~stsse~pp2hiirnnosotltwaouRsaldtitygeyeseSririssoonnooff 30 x0 fTiLi~romee5r6aq2gu5taoraetntedsrCc =805-I03 - 0S2608h00 ehnresss.. CO~t quarter S - $30,600 J oaricatap - Continue newS;L% for -- fluoro- = -m ocOCchocevttmtaaitnciolaclll/sewanatsteercrta4uitrsseteirrnitabanutstiioBoynn oie 250 25 - cSsFoeooenrmfstiafitcititciaaiznneetdn~tpBporhTfoor6u~o0rsr0mear%~~aaacnatetibioyonnHPLC 25 0 - - =mPsLuPohrosHf3I~o8aod4c4e4teEsR-age4nra,tat~aanEatnAdtiI~ioeo8unslnr0roe0iottf2fheh1a~aannlleec:,eohvoel,, I00 x -- sTc96co-rh8eEr1..1-1ffR8ii,smhoTnttooxxsioolNnnicccaicc t8p0o5se-iit0s3 ~00 aw ETT~iPimmeem2~oo2u9vaarrsttomeelrirdis39, -& EtFDSE/TDI a6B14s~5 ehnress.. Cost quarter 9 ~ $27,675 waicossess 3MA'10065559 N00 14 3M_MNO0000114 22557733..00009977 apc RSENTIAL sour 3, curser 2 [-- Year 3, Cuar~er 2 PTiority Cat_~ mm ~ Carpets new 3 to ire III psmweoowr 5, Garpp r e3 ep :r le+rm aemT-- EiomesriTieTstoa-- krn eeSpacoo-- fl10wrn-esTcmyatEesnce wiiIa2=v5e3. Year 3, Quar~r 3 = ---- -Eme --T SPia -- rooeTavEeq--is umy-- atrT Etsee--roe L1-- :--1 ---EscpiYaes ws ow=iem. III De~astaitoinn DDeessccrriippttiioonn TTiirmeeiinn bhe~ss.. - Complete n~w SAB for flucro- chemicals 250 - Measure KOC for cc 795-23 90 Photolysis Of acrylates cc 8011-24A and LI~ 2485-2 on silica 200 Time quarter 10 Cost quarter 10 - 630 hrs. $28,350 Aaalllkccaoolhhoiolnlses hLLIyR~dr33o88l44y44-s-4i4s&&oLfLRR 44119977--22 8800 photolysis on silica of surfactants EAI 80C21 and LR 5625 200 son ed fabrics Pho~olysts of acrylates u~ethanes on dyed fabrics 0300 Rigo;-ous aerobic bio- ~egradation of acrylates cc 8C11-24A an~ LR 2485-2 9O Ti~e quarter II Cost quarter II - 670 hrs. $30,150 22557733..00009988 fe 3MA10065560 swsosootts 3M_MN00000115 Er -93- SE FOENTEyIaAD vr. mesemsnces I. I- ATA.aNchN..nicHVaeellltteeFrre,,for""tFFsiinnaa3ll/7/CC7oo5mm.pprreehheennssiivvee RReeppoorrtt:: LR 33884444--44,."" 33~ LR Technical Peport, 2/7/79. 2. 2. AAT..ecNNh..nicWWaeellltteeRrre,,por""tFF,iinnaa3ll/2CC3oo/sm7pp5rreenheennssiivvee RReeppoorrtt:: LLRE 55662255,,"" 33M Technical Report, 3/23/79. 3. 3. AAT.eNcNh..nicWWaeellltteeRrre,,por""tFF,iinnae3ll/15CC/oo7mm5pp.rreehheennssiivvee RReeppoorrtt=: EEAAIT 880000"2211,%" Technical Report, 3/15/79. 4. 4. DD.LPF.. HRaaggeenn,, PPeerrssoonnaall CCoommmmuunniiccaattiioonn,, HKaayy Iiil,, 11998811.. 5. vV.. PPootthhaapprcaagg~addaa,, PPeerrssoonnaall CCoomsmuunniiccaattiioonn,, MKaayy 55,, 1Ig98822.. 5. JSJL1..u4irCevDD-oiee7rava8anna.l,,l0h2ao""fTT((hhEheeAFeIryEEfft8ffo0oefe0scc2ht1tF))ssathoooofefnnadBCBCaoaoMtntnicttcnihihnnnaaouubbwooliuuilssfi(etEAyAyiqqruuooeeetfgoohuuaEFsslgeegsssEExxppSaonopddssruuorGGrsreearoiwottstooueh) aannda B5eer haSee er B RR e Survival of ~ry of Fathea~ Minnow (Pimephales promelas)," Report %BW-78-8-263, EG&G Bionomios, Wareham, MA, August 1978. 7. WKMM.aaMsjooM.E.rroGGSSoouHyyrfeeefEnrraiecctteeBatitanntttaeseall.i,!,ocH~nuuAsmmaar"nnRMeeeppsoSSooararfctfteiebtstbyytyyioAaanrnnA:tddeehhFuEEuarnnryvvii0D:.rr31oc.noCLmmiietet1tnen3l7ltt7eeaa.,,ll AATssrppeese,ccttssToooff Inc., To The Soap and Detergent Association, May 31, 1977. . S~..intT7..ishECllannnaaabb.aarriaenwvyyC,,han*"nBBelZlooccCoonneccteennittsrrhaa.ttiioo3nn% TooeffchLLnRRic33a80l4444-R44epoiirnnt.BBlluueegglillll S5Su//n11f75i/)s7%h77 a(tnDhdeeprtei..n C00h22a22n23)3n..el Catfish," 3M Technical Report, 5. AA5.6NNL..h eW5eleltateemrrE.,= ""EESuvv"aallTuueaactthiinooinncelooff RtethpheeortBB,iioocc8oo/nn1cc6ee/nn7t8trraa(ttDiieoopnn. PPoo0t3te7en2n)tt.iiaall of LR 3844-4," 3M Technical Report, 8/16/78 (Dept. 0222). 10. SESCE.ooO.ln1Euc6..be8in1ltEK1ieeeEtsnnyytaa:,gigaoansSaooaonitnfld)d CSCSC.ooh.AArre..ppbIItti..iicooannlGG,,soorrOiiOicnnnctggta,,abnnioo""ollRRt-eeaMWlla,aaatttteeiPirruoobnnlsPsPihahasirirhpptteiidtBBtieieoottinnwwniieenneeAggnns,,uWMaaataattinnedecdrr AATCTN.oaooxcxnieiCcE.crceoionlalHtSoloerussna,yy4t..ricio1hcn3kAAa8s0SoS.,,TfHMECEp~phSSos.eTnT.mP.,i7c877aAA-001lmn771.s.ee5rr.iiiccnJ3a..annBGiG..oSStooaccEE,iiya"eettttoonyynP,,ubfflPooB.irrishTTRB.e.eedssttPieiintnntggi~ saahnn,ddPareish, aanndd Materials, 1980, pp. 78-115. 1. AAP..roWMjeeenncddtee,ll,, n""PpTrreoocgghrrneeisscssalRReeppReooprrottrtooe,nn F8Faa/tt3ee0/7oo8ff FF(llbuuaopserc.oocchh0ee5mn3~i5cc)a.allss Project," 3M Technical Peport, 8/30/78 (Dept. 8535). 12. J3F..iuWo..kinBBegelliCissollneet,,ant"".AA"nnaall3yy%ssiiTssecohoffnicDDaeelccaattRuuerrp,.ortAA.llaabbaa/mm6aa/..78SSoo(iiFlelptf.foorr0502). Fluorine Content." 3M Technical ~eport, 6/6/78 (~ept. 0502). 13. ITTTE..hhhiiessF'F..strraaaBBtttaaeiillototuuoftwtwiiaeAsssslaPcPcbeaeaarlrlnscscoauounlnlaoasaltn)tee4WdCCaoosmmfftmmrrueuoonnwmmiiaccgt~aaaaettttriiaaooSnniff,,urrsoozOOmmeccttttoohahebbepeeprrl11i9986c22116a6,,tirroee11np9p98o8o22rarn..ttd.ttoo tEhgeorSotaattes from data oTfn in AtSlhheae'bafFmooauurronqSuuWanarrstiteeerrwllayyteNMrPPDOESSSlSudRRgeeeppoorrattpssplitCcooatttihhoeen SStaknaa~ttee of ALabama. MAr0085861 3MA10065561 IM_NODOOO116 3M_MN00000116 22557733..00009999 a E-94S- a ~. ... ~ 16. T3AaJ..oSxxiliiAAe..cseaTSTSnuooutbdbdsshhttuSuaannennttccceereerress,,t,,arAAsyUsUSSssEEiifPPssoAAttr,,aannEttnLLveeAAtitdtdcememoeirnirnsnieittsnsootttarrM:.laattooRAN..rrealRRffooooosnwrree,,nPPeedDDsseettpipNicuuacitttidyuydereassl aannd ARRseesssooiuusrrtccaeensst,. SU0e..cS5r..etaDDreepypaarrfetommreennEttnvOoiffronSSmttaaettneet.,alSSeeHppetta..lth3300,,and119988N23a..tural 15.5OOS..citaaPPfn..nooomlWi%lta/aatWssaaiitatke,,enrYY..PbaaaircBB..tisiittTTnJieeoowvnDaarcaitCC,,ooeeffs M..fiiiccMn..iiesannMWttiisslllleesarrnn,,d~ aannddAquDDcs..se EE.. Aque~.us MMaarrttiiree,, ~olubilities of Organic Compounds, NBSIR 81-24~6, 1981. 1166.. oYY"".fAiEgqO~uu..reagocauuTTnsseeiwwacaSSrrooiiCll,,ouumbnpiMiW.o.liuitntMtr.d.yysWMaaisinndlrldllOeeO2crr~t5,,taa.nnSSc0..oil,/P7w..Waa3t.tWWeeearssrCiihkkaPP,,nae.rraatennEii4dntegii.oDoD..nnDaECEC..tooaec,ftMMaffar2iirt7cct~1iiiroeeenn,,tt o5f OS rganicosCeo!mpounds a~ 25.0~C," J. Chem. En~. Data, 27: 451-454, 1982. 1177.. A5AY..qq3uu:eeS0..oo7uu8ss5TT-ee1wvSS5aaoo8rrlli.iuu~]bbii1M0llM.8.ii2tt"yyWM.. ooKfMfiillOOllrreeggrraa,,nriiAcAennd~CCoom55m..ppoouPP.n.udnsWad,ass"siik3J,,., R""eCCsaaellaccruucllhsattiiNooonsn,ooff Research NBS, 87: 155-158, 1982. 16. 18. WCW5C.ll0Bee1aBa.5.rt0aa6nnNNcce1eeeee5ll3yyoo0,,ff. CC""hhE"ee1ssm9mtt7iiiisccmmaaaatlltesseddbbyyRRaattFFeeiisshhCC,,oo"-nnssttEEaannnnvvttiirrssoonnff..oorrSSccttiihh..ee TUUeppcttahaknkeeol:aanndd Technol. 13:1506-1510, 1979. 1199.. CSBCE.lin.oovTTaai..ccrecouCunChmhmmiieuuoonliuutaaattliieeoottnnSacallfoo..aff,,ncSSeee""llPPeesaaccrrttStteeeiiddcttniinooOOonnrflgpoCaCanononyeiie.fccfefiiCC3cchh1iiee0ee5mmn)nii.ttccaollaa1ssnn3,dsd7"7. Environmental Science & Technology, 11(5), 1977~ 20. TbD..hsMaiacackkzeaeyy,,, UU1nn5t7t7ii.ttlleedd nnoottee,, EEnnvviirroonn.. SSecii.. TTeecchhnnooll.. lifr: 1219-1220, 1977. 2. 5$SSS.e.oo6laDuBne1abi0nnicTee0ls1rr.i"ji8t0ecyee,,aiLnni~a5mS..iOtocacHH.t.ttaionYonYooanolllslxk-ooWoewwfatsstkkeetyyrrh,,eP~eSaaannorrddlttuiib5ttS..iiilooinCCn..tyCcVV-ooaapenllaffvvrffeatiinnciciiiti;seianontnt""ssWWaattoofefec~ OCTCreoogcteanffnnffioiiclccsoii.gieynnetVLoCCiroom.rirrtrea3elt4lai(ato1ti0nio)so.nn,op",f. TEEthnnevvIiirrSHooonmlmsuIeebnnitLtlaTailltOIy0-sSEEPccLaiireeEtnniccetSeioaa,nnndg Technology Vol. 14(10), p. 1227-12~9~ 1'980. 2222.. GNGC..neLL..iecAAtmmriioddiooynnta&sNN..inAAH..atWWeiirll,lliiaaImmnsst,i,. AAJ.SSooPllhuuabbriinll.iitt1yy1:EEgg3uu4aa3tt-ii2oo5nn Ef(Oo1rr382). Nonelectrolytes in P~ater, Intl. J. Pharm. 11:249-256 (1982). 2253.. FPB.eWxsw..onaCCloarretc,,ompDD.i.niFFc..atHHiaaoggnee,nn,, FLeL..beoP..aryWWiinn2tt4.eerr,,198aa3nn:dd SS.. SS.. LLaannddee,, personal communication, February 24, 1983. 2246.. T CCCCT..oorrerrKHeren aallnnaassttccihiheoonnaanndAdArnnAaaA..ilyyeasJJi.i.FssoLlteeuiiconn,. CCa hSvSoeuurhmbbkiss,n sttetiirttuyut seesnnaTISnttnTdde CSCooBisnineosso. ltttoaaqgnnyytte:,ss yffoorr ~;iley-In~rscience, New o~k, 1979. 25. 25. F3FJMr..ouxlevtMt..iiSccooPPEmmrrppaaRauovnsennneeiinnttttzsE,,aVapaesee~rtottoLerie-qaauLalli.idd.,~uiCC~oosmmppaauundtdtCreteeeL,rrLTnGiCCeSagaIllu9ccToLiuusll~eaas-ttuiiLiooinndss~Fleffooibrrbtrhaea,. Prentice-~all, nglewocd Cliffs, NJ, [{~0~ matonssss2 3MA10065562 _MNo0000117 3M_MN00000117 22557733..00110000 53 26. C3~cF.ooo.mmkppkKM.aae,rrriiV Vssaaaooynynndeerr,LEb,eeeott~ H,.wu."eeeevvnnaaEnnetthdhdeeee0.WW HHayyeatddd~eoo.ecpprbhhbeooeCebsehnim iedcmcd,.,.TFraraananVdgdigm7meeBBn.nN.ttia.aT TlleespstpMMt.aeea ,tt,hh1.oo~""7AddA-oss5.,ooff1q98, 2~,..~, ~ekker and Leo," Eur J. Med. Chem., V17 NI, pp. 17-25, 1982. 27. 27. TTDE..hexecre5rSh..smosodAAdy~ybCrrinraoaaanbmmmiasisccssEaannnddeoorffa3J..yLLiiokqMgK.fuu. iiddPPPrraFaMaruiutisxslxntnytiuiotrtorzezre,s,s: C""AAoSSmttNNpaaeetltwwieiststteEEiilxxccyppaarrllMeeisssssciioionbnleffoorr tthhee ZSSxyacsettseasmsn,G,"ibAbAsIICChHEEEneJr0.g.,y o22f11,,11P13a66rtl((y11997o75r8)).. Completely Miscible 26. 28. GASRG..rieeLasiL.. IAaAAppmmppTiirrddooooaannccohhneaannttddoao rt5Sto..hhreeTT..SCCrooAAerrnnrrri~ieekkull,,kaaett.ii""ooaAMnnppppualalnniiiddccaatEtAEisirsotoocnnimiamntaeooittffciioottnnhhheeydooSfcSfuourAAcrfgqafiuauaiecscooeoenuusss. SJ3.oluCChbheeimnl..ityEnE@na.and oDVaa~taasp,,or2266P::r32e88s--s33u53r,,e, 11A95l86k11.yl Aromatic ~y@rocarbons,'" 29. 29. AGNN..TooInngeLe1.hliaeetAAccimttmcirridoodAoltonlyyn~cttseehs5sSo..liisRHnnH.. PipnoYoYallaHlaalakrrktooewuSSrssoo;kkllyyvv,,Jeeonnuttaarssnnndda1Il1ISS::..ofLSSLeeoouullPnnuuhggbba,,iirllsSSiaiootctkllyysuutobboffiiicllaiilttyy ooff ASSclciiietpnnhccaeetssi;,c A66l33c(0o1122h))o,,lsppo.in11W88a58t80,e,r,1B997J4o6.urnal of Pharmaceutical 3300.. CELLM.oohlleHeenH.cl-uu-llCHHaahaarrelllln,,iVVcooall"`uuTTmmThheheeeetRaRaaenenpdllaeaavttBBtiiiiioooocnnllaoo:gOgoifficc1aaMM6lle(o5ll)esAA;ccccuttuililPrvava.irirttyyCC3,.oo9"n9mn-ee4EEcc0uvt7reti.,.ivviiJT3t.t:HyyATMeSettddoo.. Chem.-Chemica Therapeutica, 16(5), pp. 399-407, 1981. 3311.. CCCEC.oon7mmvppiT..ooruuonnCnCddhmhssieionouutBBaeeltteewwtteeSeeeaannlli.,eSnSooc""iiePPllaarrOOttTrriieggttcaiaihnoonninniocclEEoMghqgauauyttii,ttlleeiirrbb1rr7iiaa4ansn)dd,ooWWffaa1tt9NKee8oor3rnn.,.ii"oonniicc OOrrggaanniicc Environmental Science & Technology, 17(4), 1983. 3522.. o5SoS.Ff,r5OSS..3rigg6aaLLnnaaiinnccddpeeenNNoaoannnn7ddee3!i1eSeS..7cctt3rBrB5aoaonlnleeyyTrrtiajieeaeesslee,,ffrrooPPmmrreeMMddooiilccltataiirrnnggVVoolAlMuuqurmueeeeo,,ouussCChheeSSmmoooollssuuppbbhhiieellrriieettyy vol. 10, pp. 751-759, 1981. 33. 33. CB6BG..aoetetutwGG.s.eieeinncE~irreiiSSn3ggo1tieg1lsss,,, AAeTddTshshtooeeerroorpprrtteeiittSooiionncco,,aablliOOiccaattntniaddasnnsooEEl,lxx--pp~NeBe;ariratioitemcemreroennnttcPPaaeaallnrrtttriPiPateteitilloioaanonttniioonnFssahhciitroprsss, Ca3Prnno.ddeffttihihceecsi0eTPinaaotrrssaas,cc,hhllWooa1rrt9,,6e1r.9J..SoAAl~ucrbiiiecl..tleFFsoo,ooddSCC~hhoeecmmo.:ncVeVoonllt..rat229i3,,on Factors, pp. 105~-I059, 1981. 3. 34. T E CHHCE.aan.nnvddiFFn.bbrBRoooToGonGkrkrmBaaeiiononfnft,,ailCChh""TaeBVVo ev nmeaahiihppsccaoosaarrve illiPooPPerrPrrFsn rereeoososoFnpsfspeEuuert rOrrteeryTtGo,,gryin "i"ata,anEnisCECtcsthhetr iaaiCmppHnooCattas.omete,tmt priripooPoounne11unC41nad,e,MMdsasee,,vttpp-phhpl.r.Woo.idd:lss11lJ944,..--77.,LL1yy9mm9aa7.nn,, WH.. 35. 35. aSaa5F...rntedeRHBr..ePp.caa"hrYYrltaati,llintkktaiooiaolwwonnssndikkiEnyyngDn,,@..a." RHR...ch33iJO..P..no:`TsTOhOehrrenFeerbu,,lnSSedootaallamtnuun.,dbndii1i!5SE8..i~O:tts3yy.CC5,..1oo.ffVVMaecllGH1Hvv9raaa7aalln5nwgo.ii-bb,,Heeinnl~z""leeSS,nnooeellssu1u9bb8iiii2lnnl.iittyy 36. 36. SWD0..ateMMtroa,cc"kkisayyI,,na.oPPf.. MR Mn~aa.ssccB aaCrrheeenmnI.hhaassF,,S un4aaannmd~.sWl..1i8v:YYe.3.5r1SSs,hh,iiuu1,,"9t79n"".eAAnqqduuieepoouuhssee 91257. Solubility of Pclychlorinated Biphenyls, Chemosphere 9:257, 30. 37. BEW1.9yC8e0C.C..opSSottneeieecnn Oaafnn~gtanSS.ibcW..PolKKalacruiitccakknhhtoostftfb,,y H"iBoxiseoodsrorpFpittciirooonnbiaoolff PHPoyopdpurulolapatbictobinioscn,s"OrgCCahhneeirmccossppPrhoeelrrleeutaVvoonilt..s 1b100y., Mppippx..e0 2271M--i33c22r,.obi11a93l8811. 3AMrA010080565556633 aunoocoo1t8 3M_MNO0000118 22557733..00110011 ee ---------- ee KH INTIAL 38. SGG.i.veAA.g.tiVVlrraassFppiiiserh,,,AA..InMMeeTnneddceehlln;;ica""lAAnnRaaellpyyossriEtss, ffoo5rr/1/PF7ll9uuoorr(ooDeccphhtee.mniicc9aa5ll3s5s).iinn Blueg111 Fish," 3M Technical Report, 5/I/79 (Dept. 0535). 35. TK~I..nnnvttieePPzacraorropnellhhnaaaatrrssa,,eelss,,11o"998800Cii,,hnnemO0""i.PPshhtHHooruuttyctoo,szcciihhnnVeeggonmleeii.rrssttrr2((,yye4d0.Paa)}ott,,rtSSSTTuuAhhrrp.eeffraaiccHHeneaassnngddebbaaroonn-doodkkVeoorfflag, ef Envlronmental Chemistry, New York, pp. 145-160. Vol. 2, Part A, Springer-Verlag, 4400.. 3JP..iveEt..r GGFaalgginnnoo.n"n., IM""BBTiteoocashccncciuucmmauulllaattRiieoopnnortoo,ff FF5ll/uu2c2or/r7cc5cchhee(mmDileccptaa.llss 0i2inn32)TT.eennnn.. River Pish," 3M Technical Report, 5/22/79 (Dept. 0222). 4411.. JT3..ecEh..nicGGaaalggnnooRnne,,por""tFF.lluuoo1rr/oo2cc8hh/ee7mm9~iccaa(llPsseptii.nn TT0ee3nn3nn3..).RRiivveerr FFiisshh,,"" 3M Technical Report, 12/28/79 (Dept. 0222). 4422.. SoOSannam--mplSSpiiilnttgieenqSEsaEaaanRnmmEgdppliiiSsnnaaggmcppBoloioiofefsr, PSSPreeErFReddeONslisemmereervnnvattatsstiiAooaaSnnnnIddIoo0ffSS%oo0ViWi3lla,,,tearHHaaSaennantpddndtbb~eoo'mWeooWbekkaessrtr:tffeeoobwrraatteerrTHE.. Edward Berg, Editor, EPA 600/4-82-0209, September, 198~. 43. 43. EaSO~iulfouaoltillooioTgr~oyiiyccaaOoEllf'SSrFullEuPRIreetflltaddaceeaannTa~ddOaOctTLLeaeabrrboaorraanatnootdroyrFEayfri.yfb.lMMueee1ett9rnhh7tsoo3sdd..,ss ffCooorrrnMMeeelaatsseuusrrilnngHe@bertt,hhee Cornelius Weber, Editor. EPA-670/4-73-001. July, 1973. 44. YNY..ESMAlaaArrisieeaeeltt aa3l3l.3,,) S TToouxiicE ciittyyiooff n PPUllRaassc ttiicc t cCoooe smbtiuussttiiaoonnePPtrreoodduustccttss,, NTIS #PB-267 233, Sprinqfiel~'VA, 1977. 45. B AALL.ilTrT..E EE nCCvuuinppriiottnC etmv,,entFF.i aatteeEEProPcAfAf 6TTo 60oo00ex0/ii/3n cc3--58aa00nnm--dd0068HH44aaeo,zzaaArrAun ddugooguuuusssstt t.,MM1aatt91.ee98rr800ii.,aaNllssNITIiiSTnn ttEhhee 46. ERRPP#.leiPircuEcNft8.tli0euv-oDoDo2niirr2eeii1Cttnn9szaag4,,ptt8tee.du5dP..reTTaWWa..gbgogoaGaGnnonoicototedsaorrrii~isccnn.hh,,EFllaeaeInncncddterrTiirEE..ccocAeABB..eildaaiCCcsnoottagaiitstnneeggs;-CCaaS""ppyDDssmeepttebebesyyccittviiaoonnanoodff F~EooltrekkcasthrhooopBn~eeoCosnna'pDtDeuIetrteeeccRttaMiolononinotvoaaernnrs~ds.e"IIeddeennItnt1, iiFFfPirccoraactte196,piieoodnnRilensgootfosfon -EsXpStVlyiomrspvgiionvsieeias:u,msasnd October 30, ~i, and November i, 1978, Reston Virginia. 47. 47. CRB.oNenN..iniDoeilseetttsiz,,onBBrr7oo2so4kk/hh8aa1vv.eenn Naattiioonnsa]l LLeabboorrsattoorryy.. PPeerrssoonnnneell communication 7/24/81. 48. 48. GGE .. 0J.. FFE eerrbbeerr,, NNOOAAMA AAifrr RReessoouurrcceess LLaabboorraattoorryy.. PPeerrssoonnaall communication 4/28/82. 49. 49. LCL.oDmnD..icWWciiinnattleerrC,,hemUUiVuc//aVvliisss ASSnppaeelccytttrraiacaoolff CCR5Sepo88r11t221100#24(0L,R J65u8l9y),17, 1981. Commercial Chemicals Analytical Report #240, July 17, 1981. 50. 50. CGGFF..haaerrnBB--.eebUllllaaPttnnhrryggaaseevv.rrii,,oollLeeePP.tt.tteSSSSrapapsuauevcvcaeat3,grgreseaoa6su4oo,,5ff. PoaPnnee1ddrr96ft3lCCi...uloorSSroaaenn-WddNoooorrrrsffmayyai,.l--PP""eaTTrrhhaaeetftfiinngs,,"" Chem. Phys. Letters 3, 649, 1969. SI. 51. AUDA..littcrRR..aavviiCCCRooHaaIGlallle eellstoowVwaaaaatyynno,,4dr bFUF..iFltatcrrAA..uianvvtiiSSsoottllaaemempttpfossr.,AAbbssaaBoonnldrrdappstetGGi..iinoognnLL.. aSSbppLLteeoo:ccpptteerrrra;saFraoF~VVnfaa-ascce~ruus'uui~mmooubuy ssthe aRACeearrrneoodntsi.opdaaacct1eee97C8CV0oaor~poWorErrIaSTtaip~PoaEnaonTt8fos1orrr-1f8ota5rh3eSha1BtUl.6aUS.sE.itiDnoeD~eppCtta..n~soo,ff the Treasury. Prepared b9 ~he. the Treasury, M~rch, 1979, NTIS ~P~ 81-15531 9. 3mMatAo1o00s6s5e5s6a4 M0010 3M_MNO0000119 22557733..00110022 oz Gk INTIAL 52. cEC..huSSiaacnondndomorertnfyty.., v""oUUl.VV AAbb1ss5.oorrppFott.iioonn34oo3ff-3FF5ll1uuoorr1o9s7cc6aa.rcbboonnss,,"" AAttmcossppRhhaeesrraiitccs 53. EEPrEEoxni.ippvClliB8oo.ar.nssoimlKnPvvemaceeebnEnlt1trVvar,oaaolyppy,ooV,rroRleee.sxTTteaaagsoeItgal0leai,..n,nn,,tepp"".~PFPIooonollt3cteee4e.ccn3nuut-llit3Wiesa5Easls1El,,.S""AAtW1tm AAm9PLt7ooB6cmssI.oopp-ishhBpe1eRhr6riee7iccrcIiiEccIImmaip1pn9aasd7cc9tt. ooff Su. 54. NNSE SEaaitnttrEviiaaioottrS nnonoaastnllpmahehAAeneH ccrtraiaaicddlceesmCCRA hyhyeaasnneooggffaeer,,cSShcc,iiHHeeaarnnllIccoonreecccssas.,rrbb--ooNnnCCTssoIo::mSmmTiei#ttEPtttnBeoev8veei1ir-cooo1onnn8nm7me1IeIn8mnnt9tppaaaallcc1tt97EE9offo.ffffeeccttss ooff 55.55. ARNC7P~.a.histlnoiaAorrovurbbnesoeaellfdi~oclooouossnBonr'oeoeSctSmtiaielsltaeiihllcca.o.s,anfeSSS""uutRmPraerrhflndooaesttacaeaocesrddesesees,,scc",oopmSm.JppFSoooTouss2sIr8iieT,nttnaiialioo1nn9I7ooR6ffoo.ffRReeCCsshhesllaaooBILrtrrCccoonhmroeettoohfhftaannttteehhssee 56. 56. N5FSSP..ahhhteooinEKttoacooenniccnnaahhoolhee,,anmrBii7sTusa..rtierc6a1yyII6utt5oooo,,,ffofAeApaplnlnS.d~iitppahhn7Ti..aad-ttasoiOirmmccd0uusbrrfS,eaea8,,ll2oo[1igg"9")eeSS7:nrtt.aauutcda1eeii-~see8,ssHHooyy1nnd9s7rr7oott.chhceeaarcbboonnss I1.."" 57. 57. EREqE.eiol~peeeofcAAm.ritoterpsooRsRnneehiiiiesccnnrceeeorrLLj,,iie6oqc(uut8""i)iEE,ddnn$ssvv3ipiIprLz0.~oo8CnnIms225Oee448Mnn663Gtc55-,aa--5ll1108R,aeaEBnpnfeddoff1ree9cec7cc7etct.ss00772oo88,ff88--1DFF19ell9,puu,t"og.rrii33Mn1n0ee5Tr3Tr5tete.cchhnniiccaall jv Report, Project 12/27/78. 997001D100, Report 002, Dept. 0535, Si. 58. RpR5B..p.i.7nGG1.1a.55l7T-T1ihhoo-mmT-aas1ssn15,,e5i3-z34""e4VV:n,ooelleBHaanaatttnnaiiTadllbtiioozzBooaaekkttroiieooofinfnToCCffrhhrreeoommmomiifcWcVaaaalltteerrGEMr,r,rans""?npipseeCCrthhttyaaCyopptttpeefEerarsuttniis11me5m5,,,aattiiooHnno. EEmSan Treen and Methods - Environmental Lyman, ~;. F. Re~hl, and be B ForerBiatt: Ears vebenu-hill, ~eh~ior of Orq@n.lc Compounds, w. J. D. H. Bosenblatt, Eds., McGraw-Sill, 55. EEEI.anArc.A.,.i0RR1ee95i~812nn2.eerc,,inaaTnnddecWkh.nAiA.c.aSScSchehpeeeilr/lt,,, ""2SSo/oll6uu/bb8ii1lliittyy Mreeasssuurceemneennttss on on 60. AAPBH~nneAroo~pEennoryyrS8ismt0oooS0kuu2Noss,o~....,"xtX11EEh663m5Ro5M3Tz3o,:FEiTXxoe,,hcSJhuunnnbsDeieoochbharr2a0lms9i,,aennnRanne11np90o88Dp2r3iiG..tvvi,iirasiiD2boogoo/nnnl6h.,ta/re8nme1AAsan.ppnnppn.flliiibffcceoouaarunttndii~f.ooinnlhtthaeaPPcrtrr,,,oojjee+aaccfftttteerr hCTCEfho.ii2in2la5s5ct0%erTmnaOottEECriArAoITanctcoio8aonn0tncc0h0e2er1nnooftturrgmSahaii1t.txx6iaitt8oouunnrrWemeha1iotssii/mnnLaeenqwqwuauaititGveveFarar/llFeehnnnaigtt~dlastatasooTTOoa8fCCiEEbAReooIffIr 8f1190i9508l2te1pprpo,mt 80021 a C. 6.6]. HcL.oonTT7c..3enEtl1rnnaSaatbbiRaaozrnoaAwwoyyf,,e1tFM0]ee90sassRuumorrgt/eeelmsr.eeonnottkss 5oo0nn012tt.hhee pSaSovoleluubb2i6i,lliitt1yy1/oo1ff7/6LL1Rp 55662255 .62. CLLL.oosmtmD..e3r7cW,Wiiiann3lttMeerrGT,,heecnhCCniSoie--ca22at00ls7700/nN/CoscStie-ey-2be21oi15ocs1kel5((0cc0oRe1e2p8m,o00r1Lt1Ip-a-2g213e37))422.8Ss,ooAlluuu1bgb1iui/lsl1iti7t/ty8y3,1,,. 1981. .63. NLGCCL.oooapemasfmD.f.feieircWcWciii~i1oennannttlstee1,,rrC5,,heCc0CmooCSimn5-mcm-2eea2v0rl0e7cs7ii00ea/A/slCnCSa--lCC22yhh11tee55irm11ciiacclao((llccssceReAAp88nno00aar11llt11yy--t2t2#3i3i2))cc4aa2ll,PPaaPrArReuttepgiiv0uttersiirttoeonn#13,224551,,981. 6.64. ACYcSSou-eomIgemTSmufeTesizRDrtccIctiia3aan,1{llt37ss51-Cc3 928hhE)1eex.msiA iNccSPaoI0l,l2ss]lFDLPiiaUionvOvmaiRiasAsziDtceoeoennRnBrTrTOaeaeAnccn~hhdTnn.iiFFccliaauulloorrooIIccnnhnffeeoormrriimmccaaaattlliioonn Brochure Brochure Surfactants EAI 80021 an~ cc 802-23. Mnt0065585 3MA10065565 aw_No00120 3M_MN00000120 22557733..00110033 sen Fogy ne ToTApDe 65. 65. 3JFFI.oo. crTmmD0..iuulEnaLLttaaiizzoeeoncrnttt-FeeFni,,lu~voMTMtreeoommccoonhEeeSSnmuuiibbdcjjaaeealcctt:sCCoBoddeeeCCehhaaNmnnuusggmkesbeoteeerrii,,nnsJ0uunnoee 2295,.el1199T77o98.. nemo Memo indicates that cc 795-7 had been sold as a 5~% Solids 66. 66. CCSS YSoo-ommIlmmuSEeteTrirDoccJniih .aa(sll75Ch-C2hh)eemmiihBNccPeTaIat,ll,ss FEDDLiiURvvOiiRALssAiiDSoosnnSsBTrToeeanccnEghhdnniiFFccilaaauRllsorrooIIemcnnthffeeooermrriimmocaanatttliioonn Dochure Brochure 67. 67. Su=factants DR 2929, commercial Chemicols Commercial Chemicals SI omes UTE Y-ITDITDC (41.1) ~i, DBivaisinoneTechhnica al Innffeormattieonn terocehure cc 7711-27, and LR 2337-1. Division Technical Xnformation Brochure "FLUORAD'' Pluorochemlcal SUr{actant cc 68. 68. CYcSS7o-o7mI1mTmhT1eeD-rrI1Rcc.78ii,1aanl1(19a 4c8C~1h).h.iee)mmiiccSRaaIEll,ss B"DDFiiLiovUvROiiRassAiioDooenn-" TTeeFFccilhhuunncoiirrccooaascllhheemnIIiinnccffaeoollrrmmaSaStt~oiirtooffnnaaccttBBaarrnonocttchhuurree 6.~9. EcLL.ocomnD7.i.7r7cWW-iii3an,ndttee1rrC9,,8h1a.rCCioSe--s2zt7ns0o//ACcSsma22i11y55i11ce((sccocR0oB01p11e1-r-22331))344TT,hheerJrmomalayll AA2nn5aa,llyy$us9ii0ss1,,. 0.70. SSC$.oiKmmKT..earcWscheeinllaisslthha,,iChe"r"meAApiddecssraooelrrssppttiiAHoononnalhoyoeffti"cEEaAAITl 20022 nd IR Report #244, 80021 and LR 5625July 5625 en Soil." 29, 1981. on Soil," TL TpSBU3.SieMSCcvAkeTS..ieccTenEheEnrPnseteAit,,nctaaR,lbuDDilrreeFaaPssffre:,ttspsoroSPpStsorr,eiooTlsppooI2sTRs/euLeR2dlCd7e/7BSEE8Stnn.eAavvcniitdRrriaooorInnndmmeennfHttoTaar5ll0iTheTT,esesstttPDaocaSsttattaaann7d7d2aa.rcdaSuffbooprrart p HERt E h RAta Development, Proposed Rule Section L, Section 122-5, Federal Register Kia TA 4 TSCA, Part Vol. 44, No. fae 772, Subpart 53. pp. 72.72. AFAF1.o,l6ieu2uo5Mvo~e7etn-onadd1ctee6hld2eh,,6me4~d,c""saAAcilMnnastaaaArllcFPyyThrttrEoiiocjc1aeaE6elcl,Lts,MN1e"e9e7tt9h3theB.MoouddroTshelelcoochgshenyyraiccaaaannrlddNotSRSSeeueutppppooopprorootekrr,.ttvaf11f.oo/7rr11170/0FF573aa593tt7ee of opfase i(Dept. 0535). Also see 3M Technical Notebook No. 48277 page 7.73. WN3.0p..hRWi.saFFuutllillaeenrr,, S MpoovseemmeennttT ooff SSeelleeE cceteedd CchheeE mmiiccyaallsseiiR nn tsSeooiill -= A~plications to Waste ~isp0sal Problems, 1977, 76.74. TSESE~..ePEcAhSAAh-S..n6ii0c0RaRha/eel2iis-nn7eeRer7ress,-,pe0or2r""e0tBB,.,lioossPPoroerorcpjpitetuicicoteonn9soo9sff7r0oc0oC1iSa2a--e623o000r070,,0 h((eccpcoorBgs00111v1o-.2-32)42,1)", Report No. 61, bI3nHee. Dept. 75. %. . 0535, J8o/m2m5s/o8n1,. personal Comeunications. 3/21/83. 76.75. 76. ~PE~PF...rrOooRppKKDe.elICrrooEttppJiitfoeeffhSsesentrrsa,,oma4nsns,iGG..cDUePseeetRRtfrihiuuspeplloppmnoetnancTR,.leooiolslmCae.snoa"dmmffuooSRxe.rrn.oitcFbPoPrarrrritiieecisssdooicciionhnccnseeity,,,iinngg"3"/Pm2hatty2hnhys/egesi8ic3EcEno.ronvcucvihthireerrommooniirnscccmeaaeenllnnttteaalll SFaateecyorf VOregTanTiecEC,hemTiecanles,," Eco~oTep xiiccoalioo@s~t aannddfEinrvoirmomnemnenctaall 7.77. ~ SrM.oovmr.T, .sorPptiikVkeoe1,l.,. MPhI6oo(nHn3e)e., ceport with we. 294-301, 19~2. report w~th Mr. 3J.. K~eollccuunn ooff I1C6I1,. November ii, 1981. anaroosssss 3MA10065566 aw nonoor2s 3M_MN00000121 22557733..00110044 wn wna aL" -99Te. E. A. feiner. "Hlosescadation odiss of Fluagocscbons 111. 78. E, A, ~einer, "Bio~egrs~ation Studies o~ PIuorocachons ~,*' SB renee ESS Tae 3M Technical Report, Pro~ect 9970612~13, No. 5, ~ept. ~535, Ti 71~91~8. 7. kA. Selmer, "Bisgessaation Stages of Fiuersshesicais. 79. E. A. Reiner, "eiOdegradation Studies of Wluoro~he~icals," $B meparteTA S Bhneee ite! 3M Technics1 Report, Project 75-6398-29, Dept. 0222, Ts 8/12/76. 10. 3. Ted. "EAI tocai/mhotolysis Stacy using Simplazed 80. J. H. To~, "EAI 8002l/Photolysis Study using Simulated Siotioned sn Beater SE SHERRY oo, Sunlight," 3V Technical Report, Project 9776750202,. NO. 001, Sent iosie LAT Dept. 3068, 1/9/79. 01. 2. w, Toad, +p 3028 Posolysin study using Staats J. w. To~, "LR 5625 Photolysls Study using Simulated Lontion hee IRR SEE Oe. ana, Sunlight," 3~ ~echn~cal Report, Project 997675020~, ~o. 002, Senile. BA Dept. 30~8, :2/2/79. 42. 3; saan. +Tue Effects of Continuors Avueous Eipemure to 82. J. Dean, "The Effects of Contln~ous Aqueous Exposure to HE LSE of SRUNRIONER PRIS te ~4C-78.02 (EAI 80021) on Hatchab~lity of Eggs an~ Growth rad Survival of Fry of Fathead Minnow (Pimephales promelas)," Heit Sh TR Rl Report #BW-78-8-263, EG&G, Bionomcs, Wareham, MA, August ir1978. 83.5, 7, Wiison, "moe Eetests of Coneinuous Aqueous Exposure to 83. B. F. Wilson, "The Effects of Continuous Aqueous Exposure to RRR Rye tyr 78.03 ~LR 5625) on Hatchability of Eggs and Growth and Jh:oh (08,300) op punstantilyy ofbyes ped Sou bi Survival of Fry of Fathea~ Minnow (Pi~e~hales promelas)," HR Re Be Report #BW-78-6-175, EG&G Bionomics, W~reham, MA, June, 1978. 8. kT. Eisabaceny, Srulticghass pxposuce/mscovery Risse Assay 84. M. T. Elnabarewy, "Multi-phase Exposure/Recovery Algae Assay Seal aE STE Sree oe Test Methods, EAI 80021, Lot 583," 3M Technical Report, Rat SiR RHR Si SEH Project No. 9970030000, No. 007, Dept. No. 0535, 12/16/81. 05. r. 7. Cissturauy, "Fulti-pbasy Expasuce/macevesy Nisse dasay M. T. Elnabarawy, "Multi-phase Exposure/Recovery Algae Assay [ert a lor ite Ro Test Method, LR 5625, Lot 37," 3M Technical Report, Project TEI Sask he bobs rent. ma. STATES No. 9970030000, No. 006, Dept. No. 0535, 11/16/81. Ge gr meoptchoesn soxetes of n supe te: 3 ec 86. C. M. Thompson, "acute Toxicity of 3H Sample No. 2 (co RI Tre tr AAAT JE 795-7) to Bluegill Sunfish {~ macrochirus)," Static TA esi ieaneeiL tls SH ines, eieaiemempeniminl LSiatls Acute Bioassay Report #23893, A~C Ana~'~ical ~iochem~stry Laboratories, Columbia, MC, June le, 1979. 9. h.. Welter, "Muitigeneration aghnia Life Cycle Test." 3 87. A. N. Welter, "Multigeneration Daphnid Life Cycle Test," 3M Bechtel art HEE SHERRI hep Technical Report, Project No. 9~70030000, Report #5, Dept. fiir 0535, 7/17/81. mene, pacts conttcien mote user 88. Anonymous, "Partition Coefficient (n-otanol/water)" rans hie ah Teepatent, (Flask-shak~ng Method), OECD Guidelines for Testin~ I a gencys Chemicals, No. 107, p. i-9, 1981. -- 3MA10065567 ooworzz 3M_M N00000122 22557733..00110055 see -100- ,.. -i- No,T~iI, ALY 85. 89. 7TF0O5S.r.0C5o$A.Ap.osTTEEeeePPsssAA,tt, RPPuDDiulrrlleaaeeffssttS,,ecPPtOOrrioccootptpnaoaonsnseeeo4ddl!3WEEaCannthtvveseiirrrroFonaPPmrm aaetrrenttntii7tatt7alii2l,oonnTTeeSCCsseoottbeepffS SafttitiaaccnniiddLee,aannrrLtdds,,ecffotoriron T1P72r32oE%-p.1oT2s2eH-d4E,l~uRFlRe VSVooellc..tio4wn44,, 4NNooT.uSCA55,33,, PPpappr..t 171766222,544--S11u66b52p35a66r,,t MML,aarrccShhect116i6,,on 30. 90. 0T01..95S57C..9.ETEPPeAAs,,t RDDurrlaaeEtstt. PPrrVooapppooossreeddPrEEensnsvvuiirrreoo,nnmmeePnnrttoaapllosTTeeedssttRulSSettaannSddeaacrrtddionffoorr{ TTTRSSeSCCgAAAi,,stTePePrsas,rctetVRou77i7l7.22e,,s,4`S,SuVubabppRpaooa.rrrtt P5L3Lr,,.essSSpupee.rccett,ii1ooenn3Psreo77-p73io2-es-1ae1s2d2t22,-R33u,,lkearFFeeeSnddeeecrrtiaaifrlo, n 194 75. 51. AAT8nneeoosgnntiyyismmntoogeuurss,C,,heVon""liVV.caahpploo4rsr4,NPporNr.Oee.ssss1uu054cr3,ee, CCppuurpr.rvv1ee-1"26,,62,5OO6T EE-C1C6DD25GG7uuR ,iiddeeMllaiirnncL eehss 16fef,ootrr 1979. Testing Chemicals No. 104, p. 1-20, i981. 52. ASASRnnteiOoagannnlnyydadmmataoorecuudressss.,44ff.oUo~..rrSSn..osT.ShCEEAPP5AA3,TTNNeeooss1tttt6ii2cc7RPe3euu,lleeoossff1,.97PP3D~rr+iioocpopdodoesseeesgddrraaddEEaennttvviiiioozrnnoo,,nnmmeeFFnneettddaaeellrraallTTeesstt 53. TAARennesoogtnniyysCmmtuooetuurdsse,,4r4,FFniiessNshhO..BBlEi5ooo3n,ccoonnS1cc6eee207nn/2tt6,rr-aastt21l-i90oo70nn92.,TTeess1tt9,,62.EEnnvviirroonnmmeennttaall EEffffeeccttss 94. AACTSSoeTsnTttMHa--cSGSttutieianndngdeaalrirAnddceustPP,erraaccTEttoPiixAccicee5i6tE0y77/2269T9--e-88s820t0-.s.0~2v,iSSttthaa~nn9d8dF2aai.rrsddhesPP:rraaccttiiccee for for CTBMoeearncct~rriuoonciigtnnlvvnaeegntrdeteeAbbcHrrueaatttteeeerrsTi,,osxliaascnniddtPyhAAeimTppihehaiisdbbteiisiaapnnnwssii..at,h AAPFAmimseehrreii1scc5,aa8nn0 SSoocciieettyy ffoorr 55. 95. gSWT.eisEctEih. nagesMtilrlallnodenerr,aMaptJ9i.e.irciCcoa.orlnsGGu,rrteeeeePnnnheei,,lpardiaaennndtlsph7Ti.as,SAhlhgialPlcrAooAyytase1me9nay8s.0.. Boo"tTthhlee fest: E DSEUEL.exRESlpR..e~6nr0EaElp 0snrm/tvee5riin-uzrt3maoan8nlSnmc0eead1nn~e5Rttrs.aaiillgcEno,rPp1n2rru8oaottptuepbemclcsCtiticiPoooaorntniolinynoAtA:nozg,,eeanA1ccl"a9yyagn7n:,a%~al CdC~aAooattsrraavsv.aaalylIillnn~iBttssoee,.trrtpplOOrrerreeeettggaTaootetnnsii..too~nn.." EPA-600/9-78-018. 125 p., July, ~978. 96. PPBPS..aiEppEeeeLL.r.roue~tPPaoorrhtoooottfnnooe,,rccttooa""rrnEEnnovccvuiccitrreo77oin93mem55ene-3nn23tt3p,aa,r0ll"eseAAS5nss//tpp14aee23tcc//it7t77sos7.n.ooffbyTTShhSNicicessoo.ttcpbcFahehopbbbeaearSnrnaelvwoeaBBsnsrreaannndd Rees approved (Hilden) 155 for an 1977. outsi~e presentation by Mr. P. Salomon 97. 97. CC5E.aaArrAd.d8.bbooaRRur2eerdii,nn",eemrr,,3IuM ""TTBSeeiiccoohhddnneeiiggccrraaaallddaattPPiieeooppnonorrctoo,,ff ccPccroj77e99c55t--2233357TT0rr0ee1aa2tt6ee0dd0, Project 9970012600, DDeepptt.. 98. 98. AAS0nn5eoo3enn5ty,yirmooo4nuu/sss2",,2t/8OO0EEP.CChDDysGGtuueiiaddleellCiihnneeemssicaffloorrPTTreeossptteiirtnniggesoo,ff CWChahetemmeiirccaaSllossl,,ubility MFSeeetcthteoisdonsoI0s5I.,, Iot1. Physlcal 19~i. Chemical Properties, water Solubility $9. 99. GdBP.5eJ1st3Jee..irnnmiiMFdnnceaCacatStaleiilldoo,,innmeaaOonnnfFtddsss:ooDD..rrppAtADt..iirooannfLLeaacscsko3okoonn,wwssssttkkOaaiicnn,,ttt.ssSStoto7.aaffnnddoo1aarr5rr6sgd1~aa,nniiPpccrruaanccdccttehhiireeccmmeeiiccaafflolosrrs titnhhee in Scsooo~nnlssiiaddneedrraastteiidooinnmesbnyytsAR.SeTMm.Draft ~9, Oct. 7, 1981, under 100. 100. AAAnnRooEnnyymmRoouuss,,aOOEEiCCot DDn GGSuuee iisddeeerllps iiinnieeossn ffppoo.rr TT1ee7ss3tt.iinngg190oo1ff+ CChheemmiiccaallss,, NHoo.. i0~, Adsorption/Desorptlon pp. 1-23, 1981. Mk10085583 3MA10065568 W_UNC0123 3M_MN000D0123 22557733..00110066 ao Ip CT eneTImALa 101.101. vactay an. 3. tetnonn, tate of D. Mackay an~ P. J. 5einonen, "Rate of pe ArLreoRyRoR RS Low-Solubil~ty Contaminants From Water IiBpEovrsdapipoeeorsrTaatRttiio.oonn of of 102.102. AR, eandled. a"amnaiytial Atmosphere," Environ. A. Mendel, "Analytical Feshodolosy Scl. Technol. Methodology on 18 384-4," 9:1178, 1975. on L~ 3844-4," I3~ 103.103. SM, a7. dEinabarawy, Technical Report, M. T. Elnabarawy, I Technical 11/15/77. 3M Technical Notebook Notebook Ne. No. 43665. 42669, p. p. 33, 32, 100. EE1.2A/EA2..8/R7Rr7ee.iinneeRrr aaYnndg aA.,VNu..NWWeeiltteerr,, "Sclubliity "Solubility of of Lh L~ 41972," 4197-2," 33M 103.105. GSGSTF..iaeLetcouhDoA..irnRaaitctvVEiaieenlinsStggths~eWwBpaaaa#olntntraadeetdrr,vv..LEwiiInttM/?.hh8/7CVCHb9ooyy.mmdasEsrtttooocppccRhakkeo,,bbEiicc""AASOppSErppg3aaaerrHnanaittiucasIsscCffhhNooearrmmNiiCCccooaanlnrtstis,iie,"nnuu?oogJu.uessllyy 106.106. aS. vetnde,iAntalytt ica) Aestthofolosy Fish, Res. Boar4 Can. Vol. 32(i0), A. Mendel, "Analytical Methodology andpp. and Suprert." 1845-1851, 1975. Support," 3M 107. 107. Technical Report, 1/17/79. E. A. Selmer, "Distribution Costticient of 1B 4137-2, E. A. Reiner, "Dlstributlon Coefficient of LR 4197-2, Savoottteydo, reportpNorr eO13,RgBestg e eai s. Llose: n-Octanol~'ater," 3M Technical Report, Project No. in in 108.5S. aK. elsRandGc. W.a Schanda e, "Adsorption of Ln I08. 9970012600, Report No. 015, Dept. 0535, 1/10/79. S. K. Welsh and C. H. Schran4t, "Adsorption of L~ 44119977--22 oonn 105. 109. S5SS..oiirlKKe..,d"lV~?e3eiMHlsshhT,,eech""nAaiddcssaoolrrppttRiieoopnnortoo,ff IR 344int 3/22/79. LR 3844-4 on on Soll." Soil," 30 3M Technical Technical 150. 110. L3J~..eopovMrraaatxr,ccnhh,,9v/e111/e99766881o.,,rkaAsddvvaapnnroccgeeds Opogrrnggiaaenniicc SCGhhheeenmstitssatisereyy., Mectau-uiLl McGraw-Hill Book Book MI. iii. J5CE.,omWpW..aRnyTT,oodRsdN,,ew""RiLYrRork33g,884440p--.44i3BP1rh3voO-tt3oo16ll.yyussiisstUUssiiA nngg SSiimsuullasttee4d Sunish" Sunlight," 132. 112. 3M Technical Report, 8/11/81 (Dept. 3068). Asthuc bended and Commie H. Scheandt, "photodsgzadusion Arthur Menael and Connie H. Schran~t, "Photodegradation EyEoAr LT i anne arts see hr Study on LR 4197-2," 3M Technical Report, 8/6/80 (Dept. 23.!13. 0535). 2. Gageen: CW. J. E. Gagnon, C. H. nFeR HE Aqueous Solutions," So chrands s. "Bhoe tolysisltoy f Lx 4e 197-3 in Schrandt, "Photolysis of LR 4197-2 in 3M Technical Report, ~i/7/80 (Dept. 6.114. 3E 20..535E).R.GGa~ggunooA nn aannda AArrtthRhuurr rvMeenndedTl,,heb"Paohttootlolyyasiiss of of th LR Jekted 3844-4 on on 135. 115 . ESE,oilAA..,R"RSe]elRMnneeTrre,,cbn""lBsciiaool~odueeqRsrerpaaoddrattti,ioonn12aSS/tt1uu04/dii8ie1e.ss Hooff FFlluuosrrooccasrsbboonnss XL." 16. 5. BTeelcihsnliec,alSt~uedpyortN,umb1e/r9s/:78, R(CDept1.37-002H226).and 0C 337-088. 116. J. 8elisle, Study Numbers~ IRDC 137-086 and IRDC 137-0S8. auntoossses 3MA10065569 auunooonorzs 3M_MNO0000124 22557733..00110077 t-1i0r2e- IA en eTaAe 17. 117. B8WkE.iineoovdPci..ooonnccNacNmeeeeenenentltlttyryaaaltteeiittooSnncaalli..ePF,0noocttee"e"nnPPttaaaiinrraadttlliiTttoeioiffcoohnnOnCrroCCagoloaaeoennfqfiiffycciiccVoiiCCleehh.nneettmsii8.ccttaaoollpss.MMeeaai1issnn1uu13rrFF,ieeisshh1.,5"74. Enviornmental Science and Technology Vol. 8, p. 1113, 1974. 16. AATNT.eao.ccENhWhs.nni3icHW3aaee,llllttee~B1rrea7,,pp7oo7rr""SttAA,.aquu(sePP0ttrr0iiooccjjeescciTTttnoooxxil9Scca95il77bte00y0y511R23esS66tqt8u0uu0d0deiiseetRRssee::pp4oo1rr5t7tLD)Rp:KNoo41.:1997700:-112892,,.,%" Dbea33ppMHte.. 11199.. 3JN7..O5..W00..1053DB[5ee5,8aann,,318/48""4/TT-7hh49ee) EE(ofeSnfefeeaccHttaasstlscohooffabLiaCCl5ooinntttRyieinqnouuufoeousustEs sAA4sqq1u9u7eae)ono.duussGrEEoxxvppeoorssuurraneec.ttoo SES7ou8Eir.v0v.1iivvaaR~lllLRooonff3i8a4FFi4rra-yy4)RooeffpOanFFtaasHtthsheetsaachddhusrbMMeiiilntnlnentoryywso{(:fPPSiTEmcogeengppeshhsaaliaeenssdHEGSprrrooomwmetlehalsaa)n,sd*)' 120. 120. r3E~..G5&4G7T0,..20BFE,illonnnaa"IobbWmaairrTcaaewsvcaahyynR,,iecpao""lrMRtuuRllett|pii8o--Wrpp-thh7,aa8ss-ee6P-r1AoA7ljl5geg,aceeteJuAA3nss9ess7,aa0yy5310TT90ee70sSs0.tt, MeRecethphoooddr..t NoLirRn 03308884,,4-4DD,ee"pptt..3M00~35e33c55,h,ni11c22a//l3300//R88e15p..ort, Project 9970030000, Report No. 121. 121 . 9GJ~F..oniahnlaLia..inntccOeyOedsdssmEooSSnnnoociiiilnaaenndadaarnniddCC..ngCCCooC..mmCppoAAnoocnnsneddttrrr,eeSSwwyyssNss,,attveeam""mlsThs,he,"NeeaBBSSpclicoiiooneeddsnneeccggeerrSuaapddDDpiaaiovvtt.r.ii,t,oonnWCWeoeeonafaftppeoTTornnNT.ssT iinn ACQEruiaaRnnleeiO:,tyS1IEnn.nddiglaiannnae,,eriRRneegpnoorrCttentNNeoor.., AARRNLaLCvCDaOl--TTRRW--e7Ta77p00o33n2%s,, Su11p99p778o8rtNNTTICISeSntNNeeor.., 122. CAAnL-,A05F4i3r7s5t.Triester Report, 1978. ]12232.. 123. CRL, First Trimester Report, 1978. JJL..avo5D..tatJJooorhhinnesssoo,nn,, T""nFFeii,rrsstAtprTTirrliimmee39ss,tteerr19Rr8ee3ppoorrtt,, 11998811,,"" RRiikkeerr 112240.. LEEF.eaAnbAso..raetRRaoeeriirinneeesr"r5,,,! SASIanalcmma.ppc,llhiiAnnupggar,iVvleeFggoee2rtt9e,aanttii1oo91nn87,1.ffooSrr01FF.lluuoorroocchheemniiccaall UUppttaakkee,, 112255.. M~uFsSeemoopEEPoPAnAt,,eodPFP.SlleaaJcnn.tttioUBUhlppattca4akkkTweeeelsaaltnn,ddGMuTTairrdraaecnnlhssillnoo1ecc7s,aa,ttii1Soo9enn81c.TtTeiesosttnsSStt8aannddaaarrnddd.. 43DD,rraafftt peste Proposed Section January 15, 1981. 4 Test Guidelines, Sections #48 and #49, 112266.. . D. 7. P. LLaanndduuccceil,, PPeerrssoonnaall CCoonmsmuunniiccaattiioonn,, MMaayy 5, 5, 11958811.. 112277.. 3DSBJ..icioloSSedSueneurgdzguurerkka'aiidadanatsteeiittooTnnaealclo.oh.f,fnoWlw""aaomEttgtfeeyffrree-coc1Stst2oo0li1oou0uffb)b,liOOeerzoo7.nnPpeeool1lyTT1ymrr8meee0era-ars1tts.1sm."8ee3nn,ttEE1nunu9pgpv7oioi8nnrr.oonnsmeennttaall 112288.. pEDS(e..ncmtviehieLLt..nrhycyollenKKmaaeppmBalnleneatet~tnanailcTcreeetyttcFylhiaanaeattlorlde.ol,),)boigoyao""tnnBBoddi1ia2ocy(Pd*d,s1heeh0eqae)nr3rr,oa0ael0ldd3aap).ttFr:[ioooor1rnpnm1mpa8o.olo0lffd-ee13s1hPP5t8yoo5y3dll3a,eyy5s,ss,:"tt1yy9TrrAA 7Bepe8.nS.npee.lp ,,lieecdPPaootnllayyned 112295.. AATE..incuhvNi..iriocWWnaeemlllettneetRrrae,,lporM""tiAA.cqqruuoPaabrttioiiojccleocTTgtooyxr,ii3cc9ii73t0t8y0y(13)2SS,6tt0uu0ddp,iip.eessR::e5p5o-r5cct3ec5,M88u11r551b--9e117r,,9."% 00337M, Tepe o33s. iene: Technical Report, Project Dept. 0535, 2/16/79. 9970012600, Report ~!umber 007, WAIO0EETO 3MA10065570 WNOOO0125 3M_MN00000125 22557733..00110088 530. gw, Helter, navesic Tondieclety StutleBs: Ace L0330-92DtoxAL 130. IhtSiho3. KSeOltIeTrT,,esic]pcetn8e0i5es-n18sTHAqEuIaStinciTeesstiyng SReIsuRicEe.NMamE, 131. 152. E7R. RBhlnabEearauyt, "he sussic Toxteley Tesecingg: occ t0326 132. 135. SETEyeS,esTaiebn.s.AqIuRaeepiTocrtTToar.ici0e38y WDRoervkatSnhoetehet.RceETh8e2r0-e35t26C,om0pleted 133. PiT o 134. 135. Ae Sor.o"nymloTus,InORSDiGualtsn eeelniinleo is forA STheestiing eamceshemicaartse,nNae. iTrte,s, 135. 196. GS,ra5n;isvietischSandEReS7.SNofrvitus,ernA Rtcaaptkiesngriasehpneiscnetoef Extisin 136. 357. 5P, aA. Rfeies ang A.A nuttreard,eo "Bioassay on d Leachate of cc 137. 138. ER 5S5AaS.LnSe tS1eai0ner0a .e,Re"EBriPoIuSsaILtSaLEr,Isr0Sg0nhSCeonereedtSnaAIndTEtnUcSuLreRs,Gp:roteeSrhee 338. A. N. Welter, "Aquatic Toxiclty Studies: cc 8110-92 Lot 610," 3M Technics] Report, Project 9970012600, Report No. 008, Dept. 0535, 1/17/79. A. N. Welter0 "co 805-15 Aquatic Testln9 Results," 3~ Technical ~eDort, Project 9970012600, Report No. 018, Dept. 0535, 6/29/7S. M. T. Elnabarawy, "Aquatic Toxicity Testing= cc 805-24 (F-6461-1) L.R. 57495," 2M Technical Report, Project 9970012600, Report No. 038 Dept. 0535, 6/20/80. Env. Lab. Aquatic Toxicity Work Sheet cc 824-32 Completed 9/10/77. C. M. Tompson, A. D. Forbis, "Acute Toxicity of 3M Sample SSNott.aactii5ec ~cAcccuutt7ee94-BD2ii)ooaasstssoaayyBlRRueeepgpoiorlrt~t S|1u22n33f8699i66s,,h AA(BBRLCEempAoanmiaTslyy~taiTqcraIo~cBehI~aEruYs), Chemistry Laboratories, Inc., Columbia, MO, June 19, 1979. Anonymous, OECD Guidelines for Testing ChemicaZs, No. Iii, Hy4rolysls ~s a Function of pH, pp. 1-24, 1981. G. D. Ve~th an~ R. T. Morris, A Rap1~..Method of Estimatin@ Lo@ ~ for Organic Chemicals, EPA-6003-78-049, May, 1978. E. A. Reiner and A. N. Welter, "Bioassay on Leachate of cc 8010-11A," 3M Technical Report, Project #997D012600, Report No. 47, ~i/17/80. E. A. Reiner, "Bioassays on Cured and Uncured Fluorce]astomer Leachate," 3M Technical Report, Project ~9970012600 ~eport No. 62, Ii/~7/81. 22557733..00109 auntoosss 3MA10065571 suoocaonzs 3M_MNO0000126 a1 Ta AAPpPpEmNNDDILXX I AAQQUUAATTIICC TTOOXXIICCIITTYY RRAANNKKIINNGG SSYYSSTTEEMM CNaaNhIqIqeOuOumSaSaiHHttciiacacalddoottpp`ooSttxxueeiibddccsiitttttayyhhneecdedsaaff:ttooaallZlooTlwwiiiissnntcggeeddttooiInnxxllcettiihhteteyyRResescgcgaaiillsseettrryyttoooofafaiiTddTooxxiIiinnociiEEnnefttffeeserrccppttrrsseeLtiioonnffgg Chemical Substances: Description LLeCgs0o CCoonncceennttrraattiioonn SPPIIrlrnnaiasscgciithtggitlnnclciiayafillicllctayyaonnxttihncoohnhnattazoo2axrairirdcdc 11>1200i010,-,6-010-00011080,0000mnm80gga//iT1mmg/1l MSHHoZeididgeighrrhlaatytcleeytlroyyrtoicxttooicxxiicc i11G-0i1-o01e00smgg/mt19/1 Highly toxi <I mg/1 TSTSshhtntiiu'ussdVdihieeissssccchaallooeenna,,cuaatwwddehhuuililtcctahhquaawwnanaaddtssicJjudduvevetevevonneexiillillooceeppieetddyaaqquubbdaaaaasttcseiaie~ccdcaoooonnnrrggaappDennuuiibbsspllmmuiitssss,,hheeiddpnprrododsvaovaitmtieadadeessfrrooaanmbbaassiiss oopStntee6hhrressewGrpprhaeeitcccaEftthraaiimccvvttiaeeoonc:.rriussnt,,geIInnaitihnnqeuuu'aaassddtiiiadinnnlicggpttaiictttoothhonniixossifcttooisstcacyaaaallccceeuuhd,,tteaeetmaoiocnnaaaeeqcqluauanassttohhiinoobcceuulaldrdpttuootxaxbbiqieeccuiiianaatttwvyyiasa,,croremeeccoottnnhhttaartrtiibmbmuuaattnneyey pveeVtoonoontlvlveaiadintrieotioitnilnlemalmirelm tetn.ynyit,,tn..`inpaegennrvvIIsiimmtihrcppseooootnnrrammttn~eeacamnennnp,ttttaaacllataanmmdoooeennfnnggtttrhraayyttchhSehecsisesoozemenneiccceooeantatnltnhhtrdeeaarrottRniiiffooxaaannincc,,nttgooarrbbqssliTuoaoatcttaaeiororecenroccfeessnnoottlltrruuhbaabeiittlliiiioottnnyy,, prFoeetcceeeniltvviiiannlgg, aapgqeuuraasttiiisccteeennncvveii,rroonnammneednnttt..he size and mixing rate o~ the RReeffeerreennccee:: CRCSRheeherpgiglaislsrststitatemrnyneyssnaetoonnff,,ofTTHooTH.xrR: ieisccEEi..,t.EEnff,ffaaeenncc~dEttdssuEB..caoot3Jff..ioCCnhhFFeeaammiiaiirrnccccdaahhlliiWlleddlSS,,fuuabbrssEBettdassaas.nn.,ccWeeasstppb,,.i.onXX''aVV77l55aannEETddddniiettCcCiiIIioo,,tnnu,,cU0s..S5.. DfOoeErpaErOitctmcieuRnpatatiioofonnaaHllealSStaahft,eiteyyEduaacnndadtiHRoeenaallttahhn,,d WWWeaalssfhhaiirnnegg;ttoonnN,,atiDBOoC.na((lJJuunnIeen,.sti11t95u776t6))e.. 22557733..00111100 WAr0065572 3MA10065572 W3M__NM0N00000001012277 ~t sAPePrEmNDoInX 1I2I SIMM CCOE NFIEDENTIAL EohoritpaeornAc{pipEaeilnnd,CihxanTiihsecaalAsclrgDohisavs-imrsaeirfoienrcetncocoelvaerebpesttivEeeanckirnoefptoowretoSkcoaprdeeoqrnutseeesetrPstroiarntehdreiplrEyntovdhiuoscscteoncehsneeteiaioycnasld t ooorraeonimrreynt,taaclhTTihaebs.eoorrnleeytrhSeaonabScebgeirnCimUebeehrsvaCesfro:sfevleeAclutikheoodnu,aThthSeieDyaHaP cEh PhRat sONbheEoevnhes iFrs oksnl1tyahoatnohcoceo eTaenr.TyToh.isTpOe)iocm s. Tb ntohxoa LeasbcPaer sqssacrhter(12)5mmbFuarrbseswocreou(t900T.o Bn feud Bir: re 70 meron. popu orscseD rer T8hhidissotetasabrblloeedindncnclcluhudodedesestathlo~)KsEePeYrpbTprdrOoucdc~CutuHcscEttMshsICi~AhcLiihcP~hoRDarDarkU~eCTds8~pipsiDacIsu~SesCssUIenS~dSEwcwhDioitlI~he~iis.nn~ t~heet~ extooff ~thee ~rerpter.. fpoPereoadsuscet er Number cc 742-7 cosas cc 7512-2~ wm cc 773-53 wma cc 777-3 cme cc 777-4A&B cms Ic Class tiie Inert ligui4 Geetene UmeUhane setae SSuurrtfoaccttaanntt sSuurrtfaeccttaanntt Sur~actant cc 7m77e-n4B em 7711-18 @mLn 7711-27 - Ssurafatctaannt Sutactane Surfactant fe CCShheamnitocaall mNraamnee emtent rorutation (3M Synonym) ~emi~al Formulation tomas aks 05, tt) P~rfluorinated alkanes e.@., (C8F28) nariSedsoehen bottos ice Rasaies and cyclic ethers boiling (C4Fg)~4FT-Q 12Tr22020a.0t0n355g%%3e22--a9sis0letr-r~h~Ioai60snit7e/a/eTCmDDoDIisnisesplpaesll 6.775 sSuilvfeanmtisc 2acmidwater S6e6e.75oxs7ol1ve2nt7s an4 water PR. See cc 7711-27 so4~ncc 777-4AsB exegosuir an <10% FNcTc-etesaattnhheyywllTs-eiulll-enppf~oelrnraffmlsliuu~orro~-((fvFNOr-iSEEceraissmEidoeaallu)ceoocehboolal--ct) ethylene oxide adduct) carsoponee) CsFI7SO2NH [F~) C8CFo1F7ySOy20NHA-CC2aHs5 CSC(gFrIp7sSRoOu~i(CCya2tHe5)) (C~I~.20}14CH Mitpertivomsoctyl) (cpr psoneyteHanIT s3suullffoponenryyfll)l) uaaommriicnnoooc)t)-y-NlN,,)NN,N=- [Ct~FHI7SO2~C3A H6H [CR3 )3 ] +IEfoid reann trimethyl-]-propanamini~ aatoossers 3MA10065573 aw noc128 3M_MNO0000128 22557733..00111111 fp= eo 1 m0 783-38 Clase Noho nesytaze Acrylate coc T78088-1199 cec 97292-88 ccce 79904-64 cc 77955-77 ems cc 795-23 Ienrertt lliiqugied cua Catalyst caCaattaylysstt stactant ha- ccce 719966-33 ee 796-10 oman ecc s802o-2r3 cc 8s0o5-sI sSuurrtfaaccttaannte tor reas surtactant Surfactant Lom hess ~ iL OETA Csrenmaear)m Smealpolation 00Zt'-icotvcoeut+nruesrtosAelco) see see cn 13 4197-2 3044-4 Tf A0i11]7f%-oIc717-o000o Ir%/16eN1a82r-5o07E/anAt55c/F/i1el IO10yS0(oiE~nsm/cACncelWcspoI7eoh55oi00alAyn)mmSeee LR 3844-4 5211% 52% iwatenr o~her acrylate water 20% solvent NNR-ppeeelrroffrluauomorermrt~petrehonyilline CcSFsllpNO s0opnera pfylsutoerlrog~orpeholineovaiace 155s0%~ cadlimmrcehtmhyopxhyienthaytlatpeh~J~late 10045% 10~ BRE wom Test ~imethylphthalate ERL-4221 epox> resin PPieorreftll,uuooSrrooocotcchttaaamnneemismauimlliffnooenniicscaClCtoSPFITSO3-HHA2N+(GCHl2CH~O2ONH)Z2 acid, diethanolamine salt hS~33h30ahi1nniisscooelonlibisdldtse]s.ro" (TWNo,xAayNY-'2-2l,((pplih-hooeos-- o[ClQRaIIEONCHICHTT, ApeFetoIrhEarnhgeudeoir,yhdl-i)l{op)acwpchetienastnr(ueN.-nestuhlytl ea RStssoaittllcoeet~ hrs~aeloo)f)mWNmaeon~noyglandToesxei- eaterts earre,al5z%o Spireeesrnatt. i 3113.552..%10%bbeuhht~tlydrrlroonxccyayarcbbffiiottaooomlleer SSeeee ccce 880055--11C0 8(1r.7o%sswacterr o) Soe 12 4157-2 a11(c22Mi..ea55F,%0~Sw~ETeeorFaSoolcssomeE/!heEEopprlii)//taAsddiinpplinec See LR 4197-2 Piea45~c0nmi00rildlt,IosIii4,1fAap,.ire5era%22s68;;1M%e~~5m5044A~4eE/%A~/wpwwCa;e.teWee.r33,a,%1 aPnedctiIv%o~roKn.inyelthyellaecetateCaf (F) soy P.eoTh~coe-xfkryisrlusotssriuuollneiftosohnanyttilceccvayecctildso,,- SD TTrtprioiofttlanusiioscricooummeatcshiaadlntetrittater"eCFs3SO3H sulfonic acid (Triflate) Mar08SST4 3MA10065574 awuNon0r29 3M_MN00000129 22657733..00111122 iio Product. cori cc 805-10 creus cc 80~-105 cc ICUA ln :c 8010-118 con cc 8011-10 coun oc 801/-23 eccxm80i11r-e24nA ll HID com cc 811-18 Jp. cc 13-26 cCluassss Sourwf"aecutamnt omneam Surfactant US rier .- rms mime owocam tea Surfactant Surfactant amine ryt Aczylate/urethane oe Urethane ce aAccryylate - . A-4 Fiore CChheemmicicaall NMaamree (3P Synonym) GCheemmiiceanlC rFoeremmA uilnartiiconn oFe~pcr4ouecst c~ontsatiniant~og.~, 32500 25% coGrorpson-ocyinbuy SE Hy~roxy we ! agers solvent an~ 50% H20 ioc tere me so ce B050 100% FC Hydrcsy Fom~r See ~ 805-10 hr solids 90 ferels 70 let CT and 96% fluoroelastm.er Tamim RE 1% dichlor~ip~enyl 78% mole % CH2CF2 and 22 ~e % C3F6 Se sulfo~ Fy2% b~e~l ~ SREY 0.5% tri~e~l ~I a ery ~~ ~or~ EE ree ston 0.45~ tetr~le~s~fo~ Si ST 0.05% ~i~ ~la~ 200 oelasmer 7024 iH 100% fl~-~elastcmer 76/24 C~ ~C~z/C23CF~F2 seman See LR 2929 Feit ome nDmrmaricnan; Perfl~roethyl cyclorT h~l ~ifonic acid, RE die~a~l~e ~It C2.~-H2N+ { C2H4CR ) :, 23E 0HD0 o30te7ER 3s0spigR ionmerofcGto 25% 65/35 mixture of AE emulsified 95/5 MeK~SEA/ Fe BA ar~ Et~OSE/MDI 8 i 5% Ethylene glycol She70% water [EE --. 1% max. ethyl acetate ---- 20%, 98% t~DSE/MDI mom, 21 ~L emulsifier son ees 80~: water ods Trace: ethyl acetate Sr fema etr iaoee Corsomcyie 2p ac Canons CSF17SO2N(C3HT)C2S4O (O)C~C~2 Sunioossss 3MA10065575 p-- 3M_MN00000130 22557733..00111133 oCEournn cc e15-11 con cc 816-27 Shr cc 8110-~ Cmonm ~ 80021 mows L,p 2456-1 rt2485-2 wan2929 nm LR 2929-1 swe L~ 3844-4 sams4197-2 ews5062 sam L~ 5625 oaClamwsse wmtmosm stiee htm ee teem Surfactant mma Alcohol nem Alcohol wm mtn Surfactant EmiEsSee ome mnie Chemical Name ~3HS~.yponym) mwemme owe (Wide range N-Kt alcohol ) Chemical Formulation See LR, 3844-4 mam See LR 292~ eth Spm Perfluorobut-yric acid C3F~ seen ~ ~ 813-26 etieresieie cn Pcaeciriadf,,l~p~otsrsass~sisii~unlasfag~letic CdOFVIT~3K pete sites me RAPeenmrmof0nlniuiuo~nrossoaacl!tttane sulfonic CdeFnITRD3-NH4+ Arete ponies A poZyme= o 95% P.~e~q:~"ZA = S CSF1E7SOR2N{C~h3y}ICCHH2,C~2 Rarer OC(O)C~m2 Sa Rom a~ 5~ butyl ac~llat~e = C~3(C~2)3OZ(0)~2 Bde Emulsifier is 5% th~ 18/25 base~ on solidus eerie onc N-"ooecettiyhvlyh))l-nssu-al[ft(opinenyrlf]]lusgoilryvoce-iinnee,.CtdFIT7TSOR2N(C2C~A5 )SCHI2(NDOOK gHmEaHke cnmremscsc `Nee-ttehhtyyhlly))l---1l4--~pp(ee2r-rhftlyluduoroorroxoy-Ef E s octanesulfcnamide (N-ethyl EO~E alcohol) CdEFPI7RSOI2N(C2SH5B)C2,H4CR peegessme N-e thyl-N (by6rox~methyl)- CdF17SO2N (C~3 )C2HdC~ 1-perfluorooctane sulfonamide ETRE (N-methyl ~OSE alcohol) pgm ame co3ec-1ttyy{ll())besmpu~ulaldoetmc!ealf))lum~oriionm-oe)) SHEE -N,N ,N-trimethyl-l-proFEhesbalite pan~mium chlori~e (MCL emulsifier) Cd0 FI7SO2N~]Co3He6h~ ( C~3 ) 3=CL e incie, CT ~erfluorcoc~anoic acid, CTFIsCOO-NH4+ salt ans 3MA10065576 3M_MNO0000131 22557733..00111144 2 on emooR rs 1ROSACT ~EED~ FOR t4C-R~OIOLASLEO rma em Se~t i~n wate ivan cat. of IV. .2.a. mV e Priority P I 8cem~f W e--E of 1.4C Lsbel I mpcx'l'8nCe Of W- TI Hevlrlg Libel(a) Mere amie ans 0 [-- IV ned IV.C.2ob. ean lY.C.2.bo me IV.C.2.b. Acido ame peeing on~here on perfiuorFne~e~ ah corm on ry bo mean Xl Hy~rO~:~rbOn are nt ene W -- ~ay~here oan High ~o~era1~ wnHigh IHigh iv.C,2.b. nena my IV.3.2.co IV.O,2.e. ne er III ~or?lon ! I anywhere wa, IV.~.2.a. IV.E.2oa. IV.E.2.a. I.E.2.~ ic witsimpson [a III onywhore NeceS~ry ~II O~ perfluo~lna~e~ High Ill ~n~h~o L~ ill awtoosser 3MA10065577 aw_uNono00rS2 3M_MN00000132 22557733..00111155 om ann mm I.E.2.b. IY.~.2.b. Anaerobic soil I~io(:legrsds~'lon o~ LR ~4~-4 BIo~rans~a~l~ In flsh IV.F.2. b. wan IV.F.2.h, t~ fish LR 248~2 Photorysls of 8011-24A end ene LR 2485-2 Sol I blodsgrsdstlOh of eOl1-Zd^ end LR248~-2 SE wii SE ENTIAL " " "-',- - ,, .,-- .:~"~i ~ '..'-:': L re aa er Prlorl~'y of 14C Libel Hevln~ libel(a') III On perf I uor lnsTed 14odarste I1| on perf I Uor Ina?ed SL LiIX~t Ion II for portion LR 4197-2 Noderefe ve on paH|uorlnete~t p~"-tJon High Ill-fish Oh perfluorlne*sd If-plants portion Moderate II prefersbty Hc~lerole . my III preferably monomer High Footnotes: EE mee ert ot pene tren L_._~ redlola~l~ material IS preferred ~f tilting CO~I~I readily ew coer ate. SiS vat on SHtHicuin. sosalbly Insensile, virion ausomsers 3MA10065578 ateons 3M_MN00000133 22557733..00111166 ee Thi gptient irom the OV Cheriont Regulation Reporser rors che. togo-r'ible T~i8 ~1 {tom the ~ C~em~[ Re~[~t~o~ Re,order that Structure-Activity relationships w{ll take in future Assee~ment. CURR~:NT REPORT SP CSPiEERRTT mEEIoEnTNTI AiUEISNCSSRESfEaTIESsAES tmt t emi Biok~i~l l~onlrol Agonlo m a m pmn me a e cre m ene i nsera l ~al~on p~ ~ ~mine eff~ t~ ~bial e ETEETOt IIEIIAET ge i eRe e ETS fe iE ETa nBanR Mokwcrarea ottyyokp e fe and ~al ~ or~ ~ bi~ ~d ~1 "~1 ag~, ~ ~ ~ ~ ~ ~ F~e~ ~tt. Tl ~ a~ known ~ a~ ~ ~, but ~ir EE Cd ~ ~ag ~e ~ ~ ~o biolo~l ~nt~l pl FEreRok i perssciAem ntosandpe utinsd e SIm TTi INrTaAtTe E `elles,andrisks: roverammei. mses ty mt rt TUnRtEreefor maiogiB adtosr ort EE CLE lg84. Rolmu~h hlUl~lonoe se fviveEeyPy eAu~ alsToTsoeh~s~a ivm~neecletaye o~hfee~ ddeevveliopommpielsmntW ofnm~ ete ECS A ~or ~raJ ~.~ ~, su~ ~ ldenUtymg RESTRICINS ~Io~ for lden~ymg ~n ~ra~;~ic ~{~al REEEEEh 7 mprovinens ended onaber ical woadtimemoofmresntss. piso a tty ErI aEmeRnT sIeMeE nati ESARRIR BaEh SeElre EE EEt T or a voi evsS+a d et P b a A e Ar EEE SESat o ERsEm 3 Pmrmgenme emmermee mrmmmemrr a.ko will be sought tn an e~o~t "to support or e|in~nate the TESA SE DEaER eet ~ a~ a~ ai~ to dewlop mn~ "ca~b)e ~r Ee eS EESE rpe~ ese, uu~n pth, u~c~il~ a~rr~ec,t org org~is~ ~1 20, ucute, ~ub. auntcasssTs 3MA10065579 a onze 3M_MN00000134 22557733..00111177