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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
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KOIFNEFTLIUCOSRIONFATSEODRPSTUIROFNACATNADNTESLIIMNINBALToIOODN
Work done by:
Ecik Kissa
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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
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OBJECTIVES
1{ . 33
vsyu]sthromeTotgoecyerine
hfalsukceclilne
aibnorraattorbyl.oodof sa(hezpleisn.hasluabtmiigtnted to estimate the
;;
fTreovmesbloiond:blood fol MERI eXPHuce and the catfmof eTRIMicion
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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
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1. * Tshqeuaraemournototofof orignacnriecasitnlghprine in bloodonciennctreraasteisonwiitnhthtehe
vy
air inhaled.
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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.
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PATENT SITUATION
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A pocenc appicatiol
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has been filed.
Proposed Filing Action Patent action. related to this study. is not planned.
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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.
-
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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.
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TABLE OF CONTENTS
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Page
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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
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DISCUSSION
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1. sorption of [NE
in Blood.
|{d
Tshteudytecotn
taskell
WITROTET
atory conducted
TWCTIConPee Uere
acnolliencatleadUtsiiaonfgntersrautbtscheharsotneincth
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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
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DnR er A the TinCocpoeonteolcatwihooincnhi"ndienbclro7oedasevYseireslWudissthtihtnehdeeesdqIunaacrreesatsr1ia0nsitgghtorfecovery
a]
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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
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AL
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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
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* . 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)
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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
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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
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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
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EXPERIMENTAL
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The oxyhydrogen torch method (DET Method CH-9-8.3) for Tacolnotuamaolblryuitsdetfeilowunioitrnhionfbealnobwoldaofsoowdnad-sehsatesdeleretmcbeiterniemevnidendeaeedsslcercbtiytlbrueaoodndteidaienn(a4l)oi.yuntrethIraeendpodorcirgottaminboiu1ncs6t}.emdethod we'developed 15]
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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
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BLE_UI
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SokPTION oF THE COEFICIMNS
Xo AND THInEEXRAPTOBNLOEOND1:T
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Rec(owveeerkys)time
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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
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0-2
26
1
4
612
5
1 32
0.36 : o01s7 o0.z18
0.73 033 0.3;7
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"+ Calculated by the equation (8).
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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
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RatNo.
337766,884490 337766 883a51 333777666 888752458 376 850
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111. REFERENCES
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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..
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An.Ind.fiyg Assoc... 41. Sha, (b15b60.7. Roach0 , || | ;
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8. J1o6i2B.e7l1i5sl(e19a0n0d).'D. F. Hagen, Anal. Bioches. 101. 369 (? 1980).
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PUBLICATIONS
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E. Kissa
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"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
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WAEinrlaielkyy-tKiiIcsnastlaersC--chieenQniucsaetn,rtiyNteaofwtivYSeoyrnktAhnea(tl1yi9sc7i7s)D:.yespsp,. K5.19Vetnoka5t5a3,tamiann,"Tehde..
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Jumma ARTICLES
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* Ecik Kissa -- Single author, unless noted otherwise.
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2D8e3ter(n1i98n7a)t.ion of Inorganic Fluoride in Blood, Clin. Chem., 33,
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TDoecthenromli.n.ati20o.n o1f254Org(a1n98o6f)l.uorine in Air, Environm. Science
ATninnucatlo,ria1l58E4-f0f5i.cacy of Dyes and Dyeing Processes. Colourage
Sam
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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)
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cTaaptielrliaarcye SScoir.p.tio8n3. in265Fib(r1o9u8s1).Assemblies, J. Colloid and
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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.
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ai
Sa
iscab ipcee se
000688 | iaad
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vee
E. Kissa
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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
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QCNeuolanlnoutnliiotcsaitciDvyeeSsubDseittnrearPtmoeilsny,easttiTeoernx,tiolfPeolDyyReaessm.idieJn.. TAe4c5x.rtyill2ie9c0.Fi(bA1ec7re5st)a.t1e1. and
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QCPoaultayinmoteniritsca,tiaTnvdeextNDioelnteieornmRieiscn.at(JiD.oins4p4eo.rfse5D)9y7esDy(a1is5n74Ti)en.xtPiolleyacFciybleorsnit1i. ile
Ia *
Comments on Soil Release Mechanism of Acrylic Polymers, Textile
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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
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000689
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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.
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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
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INVITED PAPERS PRESENTED
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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,
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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.
=
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NA.ultM.inaDtaivoenaalndSyErmipkosiKuismsao.n CDortytoSnoilFiinnigshainndg,itsspPornesvoernetdiobny,
U1N9I7D5O... ACS/CSJ Chemical Congress in Honolulu. Hawaii. April
||
HMFoienncoihlsauhnliiuns,gm.sHaoswfpaoinSiso,oilreAdpRreilbleyasU1eN9.I7D9.O.MulAtCiSn/atCiSoJnaClhemSiycmaplosCiounmgroenss:Cotinton
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+ 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
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TRL R IPI LT Eh Ts
U.S.PATENTSISSUED
Erik Kissa
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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
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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
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