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. 0 ~~ AR 226 34k 70 --~ 000665 . ARR26 . 34bb Saino Lu | CONTAINSCONFIDENTIAL THFORMATiON. LRa Cos p-l0 it WHENRENSOPEONLNIOSNNIGBGEIRLITNYEEDOEFDD,bRIENCDGIE,PSITERNOTY. BY CCIo&spPsyueNdoN:.o:. 0T"JL-87-5 2. Distribution on last page. JACKSON LABORATORY bI oRoEnCEIVED RESEARCH AND DEVELOPMENT DIVISION TECHNICAL REPORT CHEMICALS AND PIGMENTS JERARUTS CLNTRAL INSEYCS E. 1.DU PONe T DE e NEMOURS &COMPANY! me INl FO.SSYT STN rMS | KOIFNEFTLIUCOSRIONFATSEODRPSTUIROFNACATNADNTESLIIMNINBALToIOODN Work done by: Ecik Kissa | ARpaetpperonortt'vseidwtruaibtyti:tonen by: approved by: cEriFi3Rk.. KHOiesrnsisalaenrii 7 y aPse osf teochdnical work: mgiusnti 1964 to bencigry / 1986 Personnel: Ci Gibson n and i Paul A. Saingon AnsTRACT CsluubocrhirnoenicaBnldosotduidpysaarmognpalnetseiofuoarilisg.gnxaevlelTheLbeaebKnoirnaaetntoairlcyyzeoidfnhsafoolfcapttiooirnognaniacnd vCeaolsnicmeifnonutanrtdaiotvniaonofinciee apprBiirnbealltoaeotdleydhvaoivretghanbitecheen(ldsuaeoutareciremnienreoidon.t bolfoTohdethe incceasing concentration in the air inhaled. The TCehileriamtis-nqouaratdrieeornrooKfoi|tMGtoifcet.hebuintctrthereaosmirnabgtleoopdcoosecafpefpxiepcaoirsesunctetodieomcbere.eyases with Hpoevrefvleuro;ragTehteaneoliicminat1acisiaonlinesrsbalteovoodlcaot4ei0flfeincotiethanndtisffpeeorcrtgimvomern--ootianoi+c0 catcohiondsseeqnoufaentpleyrPhetlicunooncbcoleoofcordtaatnaicroiencstahceoifrde.fore 11keT fntoalbce alnodwer than HoEo K: jve -- EE `CompanySanit. Dossnot containTSCACEL | i EETEEeer 000a666 | ren i 8 % E - OBJECTIVES 1{ . 33 vsyu]sthromeTotgoecyerine hfalsukceclilne aibnorraattorbyl.oodof sa(hezpleisn.hasluabtmiigtnted to estimate the ;; fTreovmesbloiond:blood fol MERI eXPHuce and the catfmof eTRIMicion 3 ] f contains BACKGROUND Tbhoeth obisneorrvgaatniicon lbyyorTiadveesan(d1,2o)rgatnhaitc hfluumoatninbeloohdaveseus 4: Tinocrreoactneednitchaelsintienrebsltoodi.n thIen arestteuntdiyononoftheorgeaxnpiocsure of 46: 1 cFoilocnonvdocaudensntotrioiicfaaltawicooirwndnos.er,rkesrTfshhaeanngtdiolnloginfnglgu(orfroetnohtecehn1 eatmmi0inoconan7l1iTsuinmpep(ms3.o)a.fltwaeprloeefervtapifteuoeruodnfrdlouofoclictnuoaonrtcihience 4;a a c1ida stantabloobdy hLSaessns olveraodltattoialdeeff(o1orlutosrintn aoterdeplss aurcieacptearntetleru:oercsoctcaonocnic i iTnoTneefrionBdoaposlymdeesriigsnaetdiontoprroecpelsascees.ammoniun per(luotooctansate i CONCLUSIONS | 1. * Tshqeuaraemournototofof orignacnriecasitnlghprine in bloodonciennctreraasteisonwiitnhthtehe vy air inhaled. | 2. T2TThietCeeorneslomtiramdenietnr,atijKeouittneneodtrnecgruneia@msha--elsouieivtBhl. thtenebslqrouaoatderecaoprnpotorftoixcioifneantttehse is not 3. ThepeecltiimuicnraotToiocotnTaensrcsaitcevoalccaoitediflfeidocainendnottsidtsioc(cfMogrnucmemmna--trrakteio.n.s:Hinotvheaavtierr. nt eRlently in blood are likely Go be lover than those of perfluorooctanoic acid. 4. TTheesiignnoirfgiacnainctlfyl.uoraitdeer leexvpelossurien bo lggd m incre aged saiiifghbluyt, decreased to normal values in a relatively short time. --a- q CompanySanitized. DoesnotcontainTSCACBI 000667 an PATENT SITUATION io = patent Protection A pocenc appicatiol ; 4 has been filed. Proposed Filing Action Patent action. related to this study. is not planned. | PUBLICATION STATUS The Kinetic interpretation of sorption and desorption of | vfilluloartotsyu.rfasPtuabnltiscatiinonblowoidll isbe ncoovenlsidaenrdedp.robably of general || fn blood The has method for the been published determination of (E. Kissa, Clin. inorganic Chem. 33, fluoride 253 (19871. - ~Dn FUTURE, MORK turthor woornkE =ts n-- ot pLfMnoend.121 100 study has i ben completed , and f saeery it No unusual consideiations. ENVIRONMENTAL CONSIDERATIONS No unusual environmental considerations. : D ! meee -3 GonparyBosSssoal cnoniizTSCdAC.SH 000668 RST ESR Ee see Fay on | ; . TABLE OF CONTENTS ! - B ! Page : I Discussion . LLLi.. .... ... ... 8 : 1. sorpcion ofENNin nied . . . . . . 5 2. erininacion of[EMRRtes cron Bloca. . . . 5 3. inorganic Fluoride in Blood . . . . . . .. 7 TL. Experimental o.oo... a... 6 LLL References . . . . i... ........20 ~p !i -4- 1 iS `CompanySanitzed. Doasnotcontain TSCA CEN i| 000669 i Pp. + DISCUSSION | 1. sorption of [NE in Blood. |{d Tshteudytecotn taskell WITROTET atory conducted TWCTIConPee Uere acnolliencatleadUtsiiaonfgntersrautbtscheharsotneincth || eExepoovseurrye., aWfeteranatlwyozewedeAkns,e sbilxoodweeskpse,cimaennd ftowfelvteotawleekfsivooffine by |i otuhre aonxaylhyytderogaedndittioornchmemtehtohdod (4(]6.) anTdhe focronciennotrrgaatniicon folfuoorirdgeanibcy ! CfToolntuacolernitn'reFlautibinfoinbneloiocndonbwclaoeosndt:rcaatlicounlataendd atshethienodrigfafneicrenfcleuocbiedteween the wCaosncefnoutnedatTihtooencoionfnc[cgegnaGsterEatsMixoonoMdboAnftioar3i1gcia.nyicwcoi.t(hleuxtophireneesisneicdnrenabtsloiondg. cp cp = Kc, fa | yTiheolueas thsattAraiptglhhoettvaodfliunaecssp wvofietrhatuhsetheccaoseofinfoipcelioengnatr(:iFitghK..micd1)e:csrceaalTsehseedpwloitth the oBirnicortheeaaspiSonqsguianrraeetceoFlvoyoetryb.o5ft,imcseSuG((TTeaaLbbtllaeeng11)1.)t:hatThAecyBlvoamtlayueofboeftahethfeourngceatxnpioioncnent || DnR er A the TinCocpoeonteolcatwihooincnhi"ndienbclro7oedasevYseireslWudissthtihtnehdeeesdqIunaacrreesatsr1ia0nsitgghtorfecovery a] | tTIihnntcear.iecgobpiTtnhge thrleeicneoxs-vaexrdoiys ntoaittnes5pd1aFosistaa.ntcher3s)o.ughhiTchthehe dneoocrnirigiiannce,earihwtoiywtehvoeftrh,ethibsut celationsnip at very Loo coc Lone Tequizes | more data for a definite terpret&tion. 2. Elimination of[EEcN<on B100d. antatriabbuetoerdoTehdet. pirnfelstuehoenrcienbaotdoefydomracgiaanrnlbiyocxyblyfilcuionrahicaniledastiiownnhibcl(ho3o.d6a)r:ehasv'oBlbeaecteainslsee ot concern about their long residence tine in blood; pPSeriroefcfleauscostr,aonotwcatsoatnroeTipocluacavecodil.da,tibysug|ad as the NY" diaspfelrvsoarntinaitneathe Teflon Fcheastifimce tinetnchTbrilokonecikcp:erifnlhuacloaTctuaitiveaownnoeisectkuidagcyliidoe,or[e--xFrepeo--su)rMeme :toornaogvelsow CGCorngcae ennottr1autoiroinne (c7o.6ne ce83n/tmr3ae )tioontintDYoSCEnFagiiunchaecist tta:ghe normal ccoengcaennettriajtoiroinnse cinonacietntrhaastioan8ignnLtChieciarntbloiyodelsetviall after twelve Veeks (Table 1 ~o~ "se . CompanySanitzed. Dossntcontain TSCACBI 0006770 ee---------------------------------------------- 4 . ] 5 2 || 5 AL 1 PLECHI SR (Cunt Tl) eGoltainnoiicnaanctiaPdo,pTnethbelotooddatcaotmoehaatcvheee ettohleibeamtifeintatatetdiwrohtaiotncehafKainSmetEmic--IYT:.c ebFxeapcteraeusscseoieoftnfheiwchieielncithnsi,fpaerciTnhoiintssoftish,efluchooavrlaicvnuealrta,etdiononsturoffsatcrrtaaatinegthsctocncosrrtovananrtbdsiooodf does not Obey simple Kinetics: Bfr1oucoersasc.onpFItoiruanitdssoursrduoearnllyKbilnoaeoscdsiuemooeb.devet,Thahtelikhtehaelfa-e1lmiaifsmesinaotftriaotnnhpeoorft eaFsllsiuumonirenosactoinuopnnocuonmrdpatleii:cnatbelHdoowoedfviehrras,st-otbrhedeeenrcvaeiKecidunleattciocisoonxparnofdesstthheitshehaaslefu-lnipfteion $0 Rot alvaye valid: 1 have geported on that the decrease of organic fluorine in blood during the postexposure period of a perfluorooctanoic acid feeding study approximates first-order kinetics: + log epseq x Ket @ wtilhnueorbrelionocadpteaidts sttuhiremfeaccottrnacncetqntrtiahnetibloionnoidto,fialatnhdeconkfycleunottrhieiantaritaoecnde ocsfouerfftfahicectiaenntt Cor1fo%enacstteonhnneeatbre(lalletiuimooairngniosnaeatutiineonpdntbiloBofounor:dftaheccttahanefnnltrueotphriesriensaometEontegtdammietscthuearbf{oaiclcuoitonzarceniedtnn.etfavrthoiimocnhbslorooodf.a fluorinated surfactants. cfoonnatduenrcaobnAlpelpilcocatutrevodfatu{lrioegretac-hpdorvdceeorrnsusseKqiunteeitnniteclsy(.Faig.Tshiea3)neilfeiixcmnaiinnbtaittsidoenparrtautcee of peciiuntooctanolc acid fron blood 16 more rapia in the TbheigsinnSiungggestthsanthdautrimtghe tdheesolraptttieorn patratteofof thpeertrluceorveesrsytopneoriisod. aaKtcchniieoadw`nummnooCaloldeesccaouudrllsbeeoessrdb aainronden bBtelhlroeoiodmtielnimeanastsyeidsvnatrarbtyol.ono4gdlyPfae(ch7rte.fel8lr)du.orbpaootorTetct:tlauinseToceihspcovotisensagaicnbidlsteihceisthat Bore strongly held perfluorooctansic acid molecules back. It pisecatlisvoorspoocstsainbcliec tahcatid thmeolsotcruetensgtvhardifest.hedeapdesnodripntgiveon bvoned of o adsorption blood also scshhioetwaestiiocncusrbevlraootdov.rieet (oFfifBe 4)U. THPTE devtiaotisons(7r5o0nm uSSnEicanottmripeerliivceta'otetFdhiactCiodcfrapte-tnohdfeedneptrerfVKlaiurngieratetiocicsotnacnoafanacsbaasseeerxippniiiaviemnw:epsarbsyinagn, Bocefogesacey oRPoRstion may aiso complicate di(ettsseorreopnlteirimeoi)nnataofnidon@itfkhfeienraeeitniftcisu.soinon rate of hcicohnsisntas oofoflceamcoctlueicceuhnle.es _e- CompanySanitzed. Does not containTSACB t LIFCU7303H (Cenitdl) * . of a fluoTrhienataevderasguertarcattaenccoeffrfoincibelnotodk;urfionrgtahetismleisiinnacgiivoanl wt Ot is given by the general kinetic expression i . Bert = ke cf? jay Hi where 0c is the average organofluocine concentrat! n decrease | _ Papnodstceyxptohseureavetriamgee ionrtegravnaolflAuto.rine concentration during the , It follows that log (Bc/Bt) = log ky + z log ex tay (4) i FaTLchaec0orsdt6ionnTegocTohtfoeforaeobqrfougiuaaut.tnoiotofoomnloeuc;ot(ar4)niIonnleideniccoaaFcintigcid.en.ngt5rtahTfotahrite] Te Kinerically of (iret order. Movewer: htehFloot elyiielmdiwnatinapodrineneisnpprlowocitettsehsd vapses oC kare TPnorto3cecsosnC:sotnacbnnuttq.uodnaegtc.ieyea:xspeecwteiaihfotfheanInwchrceoamspinigicarteecsove{riyrettinoerat(eTable . 10g (ep/eg) = Ke t (5) Whore ke 1s a tise dependent rate coefficient at time t. . Plotted aTghaiensltogtahreithtmauaorfeorFoasatncfofluoriinneericeotnoceentsciaratiioonnt bins in blood i (Fig. 7). Hence | 109 (cp/eg) = ke 05 ) The question remainz. why does the organofivorine c(o6n:cent"Sriantcieontheinlbllsoodsidfeits otfhetheequaetaivoantio(n5s) aarned a1ldseonteiqcuaastiotnhe right sides have to be equal | Ke t= kg 05 @ i It follows that Ke = kg / 0-5 and: the equation (5) becomes equation (7): 10g (ep/eo) = kp t / 9-5 uk; 0-5 ore . CompanySanftized.Dossnotcontain TSCACBI Ei 000672 h 1 Fe - | | =D | . DISCUSSION (Cont'd). Mthoush tho cine tasecvats, ot which onefumm-- concentration in blood was determined. were not selected for dSCoepstpfeEeroimnciiinneiannctge.lythiwteittihsimeatphpedaerpseeqnnutdareentcheartaootftheotfhveatleiumleeismi(noFfaatbiikySonv1ar0ra)yte In summary, the elimination of fluorinated surfactants from blood is a {irst-order kinetic process having a time edeqpubantdieonnt (4r)ateyieciodesffitchieenatv.eragAe lroagtaeritchomefifcicpileontt,. aKyc.corfdoirngtheto "ime interval At. aiocenitideiiaccrot.nocneAtnHtocrwvoaeamvlpetvaroern:sies.oninofbinoeo OoeiPtTRmvEocirrsut TaoreHoaencevropTehneletr.iaCirlfliuasiroaerroTsohcintmaanyoibce CPovritrloumoeznaotcaelanopircosien:TMA and pbs therolore lesser It ohould bo remembered that the disappearance of organofluorine from blood does not necessarily indicate that the fluorinated surfactant has been completely eliminated from the body. Organs, especially liver and splecn, may also harbor organic fluorine. 3. InorganicFluoride in Blood. : creased TheTrTtoainbpnl0eoa-rr0hg1Vaap7pn:sic s"GifoTighlenui.ionferaviinecdrtaeensteil,nyrol,Ithsneoaasrngbialaenotiorcdestuotilint6ucoroseobfiaidseeedxpphbaoasruessrieteto vcTaextrpuotrsnaiezgdenitttiooca4mn5ot0n.eottsnuevaM luTeMsorM gianniseM IoFileutoic1iv2d7ee"lycohs1cchoernTttuiliastitiTnaoern Ei0ae?plod Je Company Sntize.Dosnot containTSCACat 1 000673 2 i i EXPERIMENTAL ! The oxyhydrogen torch method (DET Method CH-9-8.3) for Tacolnotuamaolblryuitsdetfeilowunioitrnhionfbealnobwoldaofsoowdnad-sehsatesdeleretmcbeiterniemevnidendeaeedsslcercbtiytlbrueaoodndteidaienn(a4l)oi.yuntrethIraeendpodorcirgottaminboiu1ncs6t}.emdethod we'developed 15] s . || | ge | ! ! i . . i 000674 | | amie 1 ORGANIC FLUORINE IN RAT BLOOD tl Exphoy suroef 3 pes OcIaosvnaiekcsFluorinGeoWeireKBlood:12-WERKs, Initial Recovery Recovery Recovery | 7580.060 a202z0.o20 01a3.lo9o 480.0 wo 40ls 02U.2s9 o0ilaas Ul 1606 ai "Average values for blood samples of five rats. to - ] BLE_UI : SokPTION oF THE COEFICIMNS Xo AND THInEEXRAPTOBNLOEOND1:T || =Ae Rec(owveeerkys)time xe a | ok20 ol21.e58r17 0oa.ll6ss4 S10 Company Saniized.DossnotcontainTSCACBI ] 000675 bo LL . I . TABLE 111 : KINETICS OF FLUORINE ELIMINATION FROM RAT BLOOD Hdec(owveeerkysPeriod 021-7262 Fluorochenical ((hao1ati on) Rate CoeXtet.icient 0o.l3167 01A6verage Expo2nent 110130 1150077 20-62 Peacritdlu(ofceoeodcitnga)noic 00..373 01.0932 Average 0590 , + TABLEIY In BATECOEFFICIENTS AS FUNCTIOONF TIME PD RPeercioovder|y ARveecroavgeery oSfquAarveeraRgoeot Time Recovary oe Rate CoePfafritclieunotrsoostanei Acid (uecks) (weeks) Time Found TM CET Found Cale || 0-2 26 1 4 612 5 1 32 0.36 : o01s7 o0.z18 0.73 033 0.3;7 || "+ Calculated by the equation (8). . 5 Su ~~ CompanySanittfed. DoesnotcontainTSCA CBI 000676 DD aw. E . TABLE V INORGANIC (IONIC) FLUORINE IN RAT Bi0OD . |Lo c onc. 1| {mg.red) 00 00 444888000 80 i TRienceovery AWeeks) o2 22 00 2 . OFlrugoarniince (pom) 01.74 01.17 161114820...000 a2 FIlnuoorrgianneic (pom) i 0o.l0o1z6s 0.0.000179 ' 000...000536534 0.020 i RatNo. 337766,884490 337766 883a51 333777666 888752458 376 850 ~D + y- tH -12 - - ~o~ e CompanySanitized.DoesnotcontainTSCA Bi 0006777 | | Ce eTa He Soom F sw 8L000 _E=---- - --- r Pee EEE EE EEE ee Ee 0 E e EE eeeee ) TE TEER EE ET a TE RET Eee ee EEE | ----).. : 9 ' CompanySanitized.Does not contain TSCACBI -13- 000675 i he . TCaOeNSCEoNoTRnATIONctOForIFf ICGRUNRETe C2PRUv GRINEeIN Br LOOD VISN.AR. - Tibo-r TeLFeinns fmeoowaar Te so EE EE EE Ph FT TT TS eee A A Eri De gin TcTe T I dE TTe IA T TT TT L= okBT ERRer fro Ti mT 1| ; r semTl er h pT ; | a ee ha eit { Soll A Le wees | bp reg GREENER | E el AT eeTTGe--ar i C: lee T f] a 1 : tea1" - . ! JT CompanySanitized. Does not containTSCA CBI 000679 .. A riass-oCmLeTnRIBNAtTIOONF.PFRiOBprBiLaOoOmDocTAOLE ACID ppm EF sv ss000 Er "TM EE eee e e k NTT TE ET Tn nn Hl BRENN TS | AEN NTE ee PD None i ST : pmemmEENaN on iba Ee NC sgl EL oh ELL TS Tn eT = e---- TTT a TTT TT REL HE D i 1 TIME (wesxs) Case : ERED 000650 EI rine cnen LiroFs ricue on eon so Arm A ) ov SL000 ee ENE eT TT Tn eThe NeoGeo rEen a et Nn eh D DN wm mim nan en ree : ane" 2pNR panat :; EA ee en eT maL mT mm UmeT e TTI eTrTr coanll iq EYE steno ietirsfhamrst Domi op Eat 3 Do 3g 4 FomE tweaks) A EE Ss CompanySanitzed. Dossnot contain TSCACt 000681 TET ------ 4 aa - She : --_----_-- d= . AS ATHFEUNECLTIIMONINAOFTIFOIITNGSTURAECTOEN5CoErNm FRATi ION n IFBLOOD`| : to r ee eee e ee Am mn ] Cry em LE | r E mr e T ery er hT g yi S Eg S ea T ei D TI e SEOdE e 2 weekLy LEoTiIn pCn OTmTe Em Re TIS I: 1 SEE i Hr--e=ltay a eae es iE A [Yo E weaa a i EEEEEE nT eeee TEEeA ee fLVOR NE CONE Cy iw G409D (pm) Aih 17. [S---- ! ; 000682 # Te TAHSE AELITMUINNCATTIOINONORFAFT1IE7GO5URFCEo6PnEeRnFFUaOnRsOrOoCnTAmNnOIsCionAsC]ID . ----"_----_-- = "F FERLoROORTAORC A0T) rm -- ToT ---- - PLE Crray os EEEEERE Li : E a e rei ' D Shims [I E E EET e TTm E eee CZ ar ye e eae ee aee at Le Emme A eR | Em eee e : E r ree ee rd eeeaA R E Ee s r ERaAe R aA SE eee ae e Cae = = -- -- -- == _ =e =e---- sevomins ows bf iw 4000 (hm) : AS oe . 000683 Ann | (-- cen FLFUIOGRUIRN7 EEIN BLOOD AS A PUNCTION OF TINE Cpe Tv sai000 i} --_-- = ph ee Eee E . Er ee e eeeetSeeEe ==:: JER EE esre ee 3 =e == | |! |4 ) |] . . mead - i Eesha Eases Fone E E E EE Eoee A A Hs Es SR SHH E r Ee H er rr "IRE FE HE eee ee Seeees ee Eee es EEE see = R EE HE I H Er Ep Hr) z 7E flan) -19 - `Company Banitized.DoesnotcontainTSCACBI 000684 I" i 111. REFERENCES : qia i 23L.0 DA.aWF.ASC.:EhR.emGUT.buaeSylvo..e'css..DS.yNmRap.Dt..uSrTeeSax,voer+se22.6n1,c7,oann11.a17a"0nw5d0(s1.9(1796s6,e5e)r.. i An.Ind.fiyg Assoc... 41. Sha, (b15b60.7. Roach0 , || | ; i;i 4765... EREEl..l HKKK.iiisssssOsaapa,.,hauCACgPlni-anaJl.ni.d-C0hC0ehL.ne-m.1.4Si5n35{g,31e,9r10,74n94yP35ro((ci1.s9a8n3S))o.c.. + Exp. i Biol. Med.Ly],i iq i 8. J1o6i2B.e7l1i5sl(e19a0n0d).'D. F. Hagen, Anal. Bioches. 101. 369 (? 1980). i . ; ByJ i i 4i SSeunbtmitfotredPaftoerntApApprporvoavla:l: DSaetnte tfoorTRyepcioertding: | J 31i2s/a9r/e8s6 1123//93778566 |i ~D Date Typed: 2717/87 |I B0E0K:74ji3ve s : S20. 600685 ,| | lo 5 | le. Sh PUBLICATIONS | E. Kissa | soaks 3 "WT.echG.nolCougtyl-e,r aMnadrcEe.l KiDseskak,er.EdiNteowrsY.ork "D(e1t9e6r3g.ency. ; Theory. and BOOK_CHAPTERS Erik Kissa -- Evaluation of Detergency. pp. 1 to 89, in e"dDse.t..ergMeanrccye.l DeTkhkeeorr.y Nanedw YToerchkno(l1o9g0y6").. W. G. Cutler and E. Kissa DEeetiexcgKeinscsya. --pp.Kin1e93tictso Technology". a3n31d. Meicnha"nDiestsesrgeonfcyS.oilTihnegorayndand WG. Cutler and E. Kissa eds., Marcel Dekker. New York (1986). DTEehrkeikoketryK,isasnNadewT--YeochrSnkooill(o1g9Ry8e"6l.)e.asWe., G.pp.Cut3l3e)r taond369,. Kiinss"aDeetdesr.g.encMya.rcel oEfcixFibKeirssaSci-.encReepealnldenTtecFhinnollaongeys., S. 5. Selo, eds.. Marcel bekner. Vpopi.. 142,3 Mt.o L2e10w,iniannd"Handbook New York (1364): ~D a"EnHcdai'nsd.bKoiosS.ksaoSfe.l.lFeiS.boeirledsSR.ce.ileeMnaacsreeceaFlnidniDsTehxeekcseh.rn.oplpNo.egwy2,Y11oVroktlo.(12023,96,4)M..inLewin ' i | WAEinrlaielkyy-tKiiIcsnastlaersC--chieenQniucsaetn,rtiyNteaofwtivYSeoyrnktAhnea(tl1yi9sc7i7s)D:.yespsp,. K5.19Vetnoka5t5a3,tamiann,"Tehde.. | Jumma ARTICLES | * Ecik Kissa -- Single author, unless noted otherwise. || 2D8e3ter(n1i98n7a)t.ion of Inorganic Fluoride in Blood, Clin. Chem., 33, || TDoecthenromli.n.ati20o.n o1f254Org(a1n98o6f)l.uorine in Air, Environm. Science ATninnucatlo,ria1l58E4-f0f5i.cacy of Dyes and Dyeing Processes. Colourage Sam | 000657 TEEFee ToeTey Po Sn TAG tt E. Kissa `wid JOURNAL ARTICLES (Cont'd.) CDhertoebramtiongartaipohny.of3129H.-he40x7afl(u1o9r8o5)p.ropanol-2 in Ar. J. CSooillourRelPeuabsleica-tiPoansts. (PBroemsbeanyt,, Iandnida)F.utu(r1e9,84)C:olourage Annual, 3Ti.n7c5t4o.ria5l7Ef(fsiecearc.y of Dyes in Polyester Fibers. Textile Res. DJoenteSremriencattiivoen EoflecFtlruoodrei,deAnaatl.LoCwhCeonn.cen55t.rat1i4o4n5s (w1i3t83h).the D1e22t2erm(i1n9a83t)i.on of Hexachloroacetone in Air. Anal. Chem. 55. ADneatle.rmiChneamt.i.on54o,f T1r4a5c0e (A1m9o62u)n:ts of Sultuc in Orgganic Solvents|. SA.1lMi.ngDavMeethaondd. E.TeKxitsislae. Hehs.Rapdi..d 5a1n.d 6R5e0pro(d1u9c81i)b.le Transfer: Mechanisns of Soil Release. Textile Res. J.. 51. 508 (1981). ~ 5W3e.tti2n2g65an(d198D1e)t.ergency. J. Pure and Applied Chemistry (IUPAC) | cTaaptielrliaarcye SScoir.p.tio8n3. in265Fib(r1o9u8s1).Assemblies, J. Colloid and | MA.ethW.odsD,aveTexatnidleE. ChKeins.sa,ColCoorm.par12a.tiv2e55St(u1d9i80e)s. of Two Soiling i; DFiebteerrsm.inatTiexotniloef DRiesspeearrsceh DJyoeusnailn, P4o3l.yet2h45yle(n1e979T)e.rephthalate JKCoiounnteantiaitlcison4s3a,ndon38M4ePcahr(at1ni9i7cs9u)ml.sateofSDoielterDgeteenccgyenIcIyI.. TEfefxetcitleofResSeoairlcihng TKienxettiilcesReasnedarMcehchaJnoiusrmnaslof48,Det3e9r5ge(n1c9y701)1.. Particulate Soil. CDoelt.erm9.ina1t48ion(19of77)C.ationic Dyes in Actylic Fibers. Textile Chea. || ~~ Rll ai Sa iscab ipcee se 000688 | iaad rr mre vee E. Kissa -L JOURNAL ARTICLES (Cont d.) . QDbuyeatneStreimlteiacnttaiitvvieeonEDxeotftrearDcmitisinpoaentr,iseonTeaxnodtfilCDeyaetsiReosni.incJT.eDyx4et6si.lein48F3iPboel(ry1se5s7t6I)eV.r. Fibers . PEocliykesKtiesrsaFiabnedrsR,obeTretxtiH.leDeRtets.re,J. S4o5r.pti7o73n o(f197S5u)r.factants in K(iOnileyt)icsSoialnsd, MeTcehxtainliesmsReso.f DJ.et4e5r.gen73c6y I(.19L7i5q)uid Hydrophobic QCautainotniitcatiDvyeesDeitnerPmoilnyaetstieorn Res. J. 45, 480 (1975). aofnd DFyeoslyaicnryTleixctilSeubsFtirbaetress,I11T.extile CNQeoulanlniutolinotisacitciDvyeeSsubDseitntrearPtmoeilsyn,easttiTeoerxn.tiolfPeolDyRyeaesms.idieJn,. TA8e5cx.rtyill2ie9c0,Fi(Ab1ec3r7es5t)a:t1e1.and | QCNeuolanlnoutnliiotcsaitciDvyeeSsubDseittnrearPtmoeilsny,easttiTeoernx,tiolfPeolDyyReaessm.idieJn.. TAe4c5x.rtyill2ie9c0.Fi(bA1ec7re5st)a.t1e1. and | 5 QCPoaultayinmoteniritsca,tiaTnvdeextNDioelnteieornmRieiscn.at(JiD.oins4p4eo.rfse5D)9y7esDy(a1is5n74Ti)en.xtPiolleyacFciybleorsnit1i. ile Ia * Comments on Soil Release Mechanism of Acrylic Polymers, Textile | Chem. Col. 5. 232 (1973). CMhoedme.l PCoalr.ti5c.ula2t5e0 S(o1i9l73s).for Soil Release Evaluation, Textile A45d.sor8p6ti(o1n973o)f Particulate Soils on Textiles, Textile Res. J. Kinetics of Oily Soil Release, Textile Res. J. dl. 760 (1971). ] ATexRteiplreodCuhceimb.leCoMle.tho3,d 2f2o5r t(h1e971E)v.aluation of Soil Release, ; ASoiRlapiRdesiasntdanRceep,roTdeuxctiibllee MReest.hoJd. fo41r. th6e21De(t1e9r71m)i.nation of Dey Lightfastness of Reactive Dyes, Taxtile Res. J. 41. 715 (1971). Urea in Reactive Dyeing, Textile Res. J. 39. 734 (1969). HP ] 000689 4 "ye d : || 0 PUL ATIS E. Kissa | JOURNAL ARTICLES (Cont'd.) ATmheerr.motDyiexsatt.ioRnepo.f 5V6i.nyl1s06ulf(o1n3e67)T.ype Reactive Dyes on Cotton, EIrniokrgaKniiscsaSaalntdsMaasinuSamSpeleeperAed-dYiltliov,esTuinngCsatrebnonTrianodxidHeydranodge`n|| Analssis, Mikrochem. Acta 1967. 287. i bi CSoocn.du1c1t2i.vit7y16An(o1m9a6l5)i.es of Dimethyl Sulfone, J. Elei ctrochem. JS.oluCotliloonisdofScAilenkcaeli13M.eta2l79Ca(r1b96o4x)y.late Mixtures : in Hydrocai rbons: HSyodlruobcialribzoantioSnolvoefntLsi.thJi.umCaClalrobiodxylSactieesncewi1t8h, Ca1r47box(y1l9i6c3)Acids in SCoollluobiidlitsycieonfceAlk17a,li85M7eta(l196C2a)r.boxylates in Hydrocarbons, J. T4.he89Iso(l19a6t0i)o.n of Microbalances Against Vibrations, Microchem.J. TChoentaMiincirnogdeAtlekramliinatainodnAlokfalCianrebonEaratnhd (1957). MHeytdarlosg.enMiicnroCcohmepmo.udn.d1s. 203 : - 25- i 000659 8 tet INVITED PAPERS PRESENTED B SDoectieertmyinaNtaitoinonaolf MOeregtainnogf,luoCrhiicnaegoi,n AIi1r1,., 1S9e0ptth. Am1e98r5i.can Chemical . Wetting and Detergency. 186th National Meeting, Washington, American Chemical D.C., Aug. 1983. Society EMevcahlaunaitsimosn ooff DSeotielrignegncayn:d DNeatteurgreanlcya.nd MSoodilel ReSloielass,e FViinsiucahlesa.nd DSepteecrtgreonpchyo,toCmleetmrsicon SoUinliveErvsailtuya.tioFne.bruaCroynfe1r5e83n.ce on Soiling and Wetting and Detergency. (Topical lecture.) The Fourth JIenrtuesranlaetmi.onaJlulyCon1f98e1r.ence(SopnonsSourrefdacebyanTdUPACCo)l.loic Science, || MEeveatliunagt,ioNnewof OrDleetaenrsg,encMya,y A1m9e81r.ican Oil Chemists Society Annual !i CtahpeiNlolratrhy ASmoerrpitciaonn CionntTienxetnitlesi.ncl.Setchoend1C8h0etmhicAaClS NCaotnigorneasls of MLeaestiVnegg,as.Aug. 1980. Symposium on Reactions at Fiber Surfaces. = |i! ~0)i NA.ultM.inaDtaivoenaalndSyErmipkosiKuismsao.n CDortytoSnoilFiinnigshainndg,itsspPornesvoernetdiobny, U1N9I7D5O... ACS/CSJ Chemical Congress in Honolulu. Hawaii. April || HMFoienncoihlsauhnliiuns,gm.sHaoswfpaoinSiso,oilreAdpRreilbleyasU1eN9.I7D9.O.MulAtCiSn/atCiSoJnaClhemSiycmaplosCiounmgroenss:Cotinton | + MKeienteitnigc,s CohficDaegtoe,rgeInlcly.., AuPga.rti1c97u7l.ate Soils. 174th ACS National . Soiling and Detergency, Fiber Science, 1975. Gordon Research Conference, Textiles: Sorption of Surfactants in Polyester Fibers, Meeting, Philadelphia, Pa., April 197%. 169th ACS National Kinetice of Detergency. City, N.J., Sept. 1974. 168th ACS National Meeting, Atlantic i - 26 - ! . : i 000691 BTR a 3: 3 f i 3 i i TRL R IPI LT Eh Ts U.S.PATENTSISSUED Erik Kissa i i 1961 US 3013 i 865 cHoymdproosciatriboonnssoluble alkali metal 1965 US 3106 204 pDyreo-cpeasds. h|ot-chemical-treatment dy'eing 1966 (US 3 290 262 Fiber-ceactive dyes 1967 ' [US 3313797 1967 US 3321 457 Stabilized tiber-reactive dyes W2Pa.h3tonedyrilcashzoiolopuryb0rl-ae6z-odqlyuoeinsneooxfsaelrtihieensylceoanrtbaoinnyilnagninao substituent 1963 US 3 453 038 C(oCmopianrvtemnetnortsedP.eleMcantorsocharndomiC.c Wdaemv1iicge) 1570 US 3507 850 Folyneric fugitive dyes derived from Gamcueiltdlhoancairncydlaaatceiddyealgkmryoolnuopmseesrtaenrdc,oanmteamtiehntiahncagrcryylliocyl Soup (Coinventor W. Conon) 1972 US 3 660 008 fDiybeeirnsg wsiutlhfonaanteadqueaonuisonidcisppeorlsyimoenricof a salt and an aryleuifonate NM | | i& |7 1973 Us 3 765 835 acAtanytiliosonuniliccfodndiaystepeearnsdiona osfeleactseadlt of a 1973 US 3778 226 cDoumrpaobsliet-ipornesss and sofl-release 1977 US 4 063 889 SPuHoalllfyooesssotulecvrceinwntiattdehyeaicnnaigtoinopsnr.ioccesdsyesforhaving . Ley 4 4 TEA T R E A NIE IVES AS 000692 ; A La CT Im re ar rr rT a i lMCA AB 1. se ion, muLrrioCnH,EMI=RCEASLSJESPAAERCCACKTNHSRDOOANSPNCIDLOGBPHDOYEERNVTNAESTLDOODRPPEYHiPEYANSRTITcMAELNTTESTING . . [I CopyNo. 32 LSat.borRaetsoerayrcMhanSaugpeerrvisor . Research Director 56 710 n Researen Supecvicor E. Kissa CJ.. Jb.. JHeensssloenr cE NE. toens) Keavse) mm Tue Central Jackson Report Index Lavocatory Files [a $ Wsavse : | : pi 000693 r eT