Document 6RnRxLnNMNYY8z6wZOxR1bDQm
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000665
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C&P No.: JL-87-
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JACKSON LABORATORY
I /v.;
RESEARCH AND DEVELOPMENT DIVISION TECHNICAL REPORT
CHEMICALS AND PIGMENTS DEPARTMENTI CENTRAL JNr.^y..
E. I. DU PONT PE NEMOURS 8. COMPANY JMEQ. SYSTrM^
KINETICS OF SORPTION AND ELIMINATION OF FLUORINATED SURFACTANTS IN BLOOD
Work done by: Report written by: Approved by:
Erik Kissa
Iyv*
Erik Kissa '/
C, J. Hens 1e r '
by: R . Or tolan i
Type o technical work: Period covered :
August 1984 to February 1986
Personnel :
'Ward Gibson and Paul A. Sai neon
ABSTRACT
Blood samp of a Haskell Laboratory inhalation
subchronic study on
have been analyzed for organic
fluorine and iaargan
jjoriJe. The kinetics of sorption and
elimination of
blood have been determined. The
concentration
related organic fluorine in blood
was found to. incr
approximately with the square root of the
increasing
concentration in the air inhaled. The
elimination
from blood appears to obey
first-order ki
the rate coefficient decreases with
the square root of the increasing postexposuce time.
The elimination rate coefficients of
and
perfluoraactanoi^acid in blood do not dif'ferlffeat ly.
However,
is less volatile than perf luotooctanoie
acid rnd the concentrations ofPHVHIIIlQin air and
consequently in blood are therefore n x e T y to be lower than
those of perfluorooctanoic acid.
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OBJECTIVES
To determine nuotine in rat blood samples, submitted Haskell ,,laboratory, of tfog inhalatj^n
suffFhronlc study r o | H p v | t o estimate t h e f e M n levels in blood follewuJgexposure and the c a t^ofelimi fiat:ixon from blood.
BACKGROUND
The observation by Taves (1,2) tbat human blood serum contains both inorganic fluoride and organic fluorine have increased the interest in the retention of organic fluorochemic&lB in blood. In a study on the exposure of industrial workers to fluproehirmicals (3), elevated fluorine concentrations, ranging from l to 71 ppm. were found in the blood of workers handling the ammonium salt of perfluoro octanoic acid. The long retention time of per luorooc tanoic acid in blood has lead to efforts to replace perfluorooctanoic tcid saltanbv less volatile fluorinated surfactants.
an ammonium salt of a sulfonic acid derived from felomer B.Twas designed to replace ammonium perf luorooctanoate in Teflon polymerization processes.
CONCLUSIONS
1* Jhe amount of organic flu ine in b! pd increases with the
1 square root of increasing,
oncentration in the
air inhaled.
2. The elimination
rom blood approximates
first-order k i n e t i TM . However. the rate coefficient is not
a constant, l?ut decreases with the square root of the
increasing postexposure time.
3. The eliminati on rate coefficients o f H M M M | | | M a n d that jQf perfTuoroo ct.anoic acid do not d i f TM r markedly. However, M H i B less volatile and its concentrations in air 'and consequently in blood are likely to be lower than those of perfluorooctanoic acid.
.4 The inorganic fluoride levels in blondincreased slightly,
if significantly. after exposure to M i n air but decreased to normal values in a relatively short 1: . *
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Patent Protection #
PATENT SITUATION
Proposed Filing Action
Patent action, related to this study, is not planned.
PUBLICAT1ON STATUS
The kinetic interpretation of sorption and desorption of fluorosurfactants in blood is novel and probably of general validity. Publication will be considered.
The method for the determination of inorganic fluoride in blood has been published (E. Kissa. Clin. Chem. U , 2*3 (1987]).
Th- [inhalation study has been corapleteu and
further wot! s n o t p l ned.
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SAFStY
No unusual considerations.
ENV1RONMENTAL CONSIOEHATIONS No unusual environmental considerations.
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t- i:
TABLE OP CONTENTS
'
Di&cu&6ion 1. Sorption o c H p M H H H Q i n Blood . 2. : Elimination o f B P P H K a s irom Blood, 3. inorganic Fluoride in Blood . . . .
Page .6 .5 .S .7
li Experimental
8
n i . R eferences - .
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DISCUSSION
I. Sorption
lation subchronic
study on
___ using rats as
the test Thimals. 'BTbod samples were collected after the tenth
exposure, after two weeks, six weeks, and twelve weeks of
recovery. We analyzed the blood spec imen for total fluorine by
the oxyhydrogen torch method [6] and for inorganic fluoride by
our analyte addition method J4J. The concentration of organic
fluorine in blood was calculated as the difference between the
total fluorine concentration and the inorganic fluoride
concentration in blood.
The concentration of organic fluorine in blood, Cfc,
was found to inc^^seexfiil|ntially with the increasing
concentration
air, ca , expressed as
kcn
(1)
A plot of Cfc versus ca on logarithmic scales
yields straight lines with the slope n (Fig. lj. The plot
6hows that the values of the coefficient, k, decreased with the
increasing recovery time (Table 1). The value of the exponent
n is appoximately 0,5, suggesting that may be a function
of the square root of ca (Table II). A plot of the organic
>ncent rat iori in blood versus the square root of .
___ Jconcentrat 1on in air yields indeed a straight line, the slope of which decreases with the increasing recovery
time. The lines do not pass through the origin, however, but
intercept the.x-axis at distances which decrease with the
increasing recovery t
The nonlinearity of this
relat ionship at very 1
concentrat ;ions requires
more data for a definite^TnterpretSTion.
Elimination of
from Blood.
The presence of organic fluorine in blood has been attributed t. fluocinated carboxylic acids which are volatile and absoroed in the body mainly by inhalation P.6]. Because of concern about their long residence time in blood, perfluorooctanoic acid, us^iasth^^lispersant in the Teflon process, was replaced, b y p H H H M a fluorinated surfactant of low volatil:
___________ ichronic inhalation study o n H B H H I B Q 6howed that P I -- W like perf luooctanoic acid,^iso has a long resiafthce tlme"fn blood. Tu^v^jeekfU*fter exposure to a low
concentration (7.6 mg/m3) offlMHHflHHj *n air the organof luorine concentrtionnin D io o a returned tCL_a normal
level. However, rats exposed to higher^_ concentrations in air had a significantly elevate organofIjorine concentration in their blood still after twelve
weeks (Table I).
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Inonder to compare the rate at whichjj^HHHIHVlis
eliminatsiP't'Tom blood to the elimination, rate WP'perf luol
octanoic acid, the data have to be fitted to a kinetic
expression which permits the calculation of rate constants or
rate coefficients^ This is, however, not straightforward,
because the elimination of fluorinated surfactants from blood
does not obey simple kinetics.
I
It is usually assumed that the elimination of fluorocompounds from blood obeys, like a mass transport process, first-order kinetics. The half-life of the fluorocorapound in blood has been used to express the elimination rate. However, the calculation of the half-life assumes uncomplicated first-order kinetics and this assumption is not always valid.
1 have Reported ["J that the decrease of organic fluorine in blood during the postexposure period of a perfluorooctanoic acid feeding study approximates first7order kinetics:
log Cb/c0 kct
(2)
where cj, is the concentration of the tluocinated surfactant in blood at time t, c0 the initial concentration of the fluorinated surfactant in blood, and k r the rate coefficient of the elimination of the fluorinated surfactant from blood. If the fluorinated surfactant is not metabolized, which is a !reasonable asssumption, then the organic fluorine concentrations in blood can represent the concentrations of fluorinated surfactants.
A plot of log cj> versus time (Fig. 3) exhibits
considerable curvature atid consequently a significant departure
from uncomplicated first-order kinetics. The elimination rate
of perfluorooctanoic acid from blood is more rapid in the
beginning than due tag the latter part of the recovery period.
This suggests that the desorption rate of pertluorooctanoic
acid molecules in blood may vary. Pertluorooctanoic acid is
known to adsorb on protein in blood [7,8). it is possible that
the unadsorbed and the less strongly held perfluorooctanoic
acid molecules are eliminated at a faster rate, leaving the
more strongly held perfluorooctanoic acid molecules back. It ,
Is also possible that the Strength ofe. the adsorptive bond of
perfluorooctanoic acid molecules varies, depending on the
adsorption site in blood.
''
A first-order plot o f p B M B B W e l i m i n a t i o n from,
blood also shows curvature (FigT4). Thff deviation from
uncomplicated first-order kinetics can be explained by an
adsorptive site dependent variation of adsorptive ponding,
similar to that of the perfliu^ooctan^c acid. Thfe
heterogeneous composition
may also complicate
its elimination kinetics.
consists of molecules
(telomers) of different c h J m ^ T e n g W & h ^ l ^ t i a i ^ f f e e t the
desorption and the dif fusion rate
molecules.
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The average rate coefficient kt for the elimination
of a fluorinated surfactant from blood during time interval
At is given by the general kinetic expression
j. 1
Ac/At * k ct2
j (3)
where he is the average organofluorine concentrt' n decrease and Ct the average organofluorine concentration during the r postexposure time interval At.
It follows that' log (Ae/At) = log k t 4 2 log ct
; ]|j (4) ;
The organof luorine concent rat i ^ y ^ r M b i ^ d are plotted according to equation (4) in Fig. S f o r f l H H B H V u n d in Fig. 6 for perfluorooctanoic acid. The plot yield# lines with the slope of about one, indicating that th elimination process is kinetically of first-order. However, the values of kt are not constant, as expected for an uncomplicated first-order process, but decrease with the increasing recovery time (Table 1X1), Consequently,
log (Cb/cQ ) kt t
(!>)
where k* is a time dependent rate coefficient at time t.
The logarithm of organofluorine concentration in blood
plotted against the square root of time yields straight lines
(Fig. 7), Hence
i
log <cb/c0 ) * kc t0 -*
(6)
The guest ion remains, why does the organofluorine concentration in blood fit the equation (5) and also equation (6). Since the left sides of the equations are identical, the tight sides have to be equal
kt t * Kt t0 '5
(7)
It follows that
kt kr / t0 '5
(8)
andt the equation (5) becomes equation (7):
log (cb/c0 ) kr t / t0 *5 kr t0*5
(9)
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Although the time intervals, at which the concentration in blood was determined, were not se determining the time dependence of the elimination rate coefficient, it is apparent that the values of fct vary approximately with the square root of time (Table IV).
In summary, the elimination of fiuorinated surfactants from blood is a first-order Kinetic process having a time dependent rate coefficient. A logarithmic plot . according to equation (4) yields the average rate coefficient, kt, for the time interval At.
A comparison of t h e nd 'perf luorooctanoic acid concentrations in bloodsuggeststhat the rate coefficient values^y^iniortLC fiuorinated surfactants may be similar. H o w e v e r j H H H H H H i s much less volatile than perfluorooctanoic acid and poles therefore a lesser environmental problem.
It should be remembered that the disappearance of organofluorine from blood does not necessarily indicate that the fiuorinated surfactant has been completely eliminated from the body. Organs, especially liver and spleen, may also harbor organic fluorine,
3 Inorganic Fluoride jn,B^logd. The inorganic fluoride in the blood increased t perhaps significantly, as a result of exposure to (Table V). The average inorganic fluoride value
rncreasedTrom o.oiv n^i^con^LOl samples to 6.OSl ppm after exposure to 460 mg/m __P H H l i n air. If this increase was significant the norganic fluoride concentration .in blood returned to normal values in a relatively short time.
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EXPERIMENTAL
The oxyhydrogen torch method (CD&.T Method CW-9-8 -3) for combustion of blood has been described in our report [6], Total fluorine was determined as fluoride in the combusted analyte with an ion-selective electrode [4J. Inorganic fluoride in blood was determined by an analyte addition method we developed [51.
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TABLE I 1ORGANIC FLUORINE IN RAT BLOOD
Exposure X o n c of
( P # 'r i11
0 7.6 58.0 480.0
ppm Organic Fluorine ir. Blood*
2-Weeks
6-Week6 12-Weeks.
Initial Recovery Recovery Recovery1
2.0 10.2 42.0
147.0
0.9 4.0 13.0 40.5
0.9 1.8
7.2 16.6
0.4 0.6 2.2
4.4-
Average values for blood samples of five cats..
I
TABLE,II
SORPTION Of Ih B H B 1n rAT BLOOD: THE COEFFICIENT K, AND THE EXPONENT n
Recovery time ___ Lwgeksj__,,
0 2
6
.kt.
2.87 1.31 0.67
,
n
0.64 0.56 0.53
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TABLE III KINETICS OF FLUORINE ELIMINATION FROM RAT BLOOD
*
Recovery Period (weeks)
0-2 2-6 6-12
i
0-2 2-6
Fluorocheraical
M
(iTwialaTi on)
perfluorooctanoic acid (feeding)
Rate Coefficient
Kr
0.36 0.17 0.16
Average
0.73 0..33
Average
Exponent 2
1.10 1.03 1.07 1.07
0.92 1.03 0.98
t IM^LXY
RATE COEFFICIENTS AS A FUNCTION OF TIME
Recovery Period
Lwec&si
Average Recovery Time
(weeks)
Square Root of Average Recovery Time
Rate Coefficients
^ga -
Peri luorooctanoic
Found"1'"" CaTc.*
Acid Found Calc.*
0-2 2-6 6-12
1 '1 42 93
0.36 0-17 0.16
0.18 0.12
0.73 0.33
0.37
* Calculated by the equation (8).
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TABLE V
INORGANIC fIONIC) FLUORINE IN RAT BLOOD
JgxPQ&uce 8
i
Recovery . Organic
Time
Fluorine
(Weeks)
(ppm)
Inorganic Fluorine (ppm)
i
Rat No.
0 0 0
0 '! j ! 480 f 480 480 480
0
1.4 i
0.016
2 0.7 i 0.025
2 , 1.1 2 0.7
0.019 0.007
0
140.0
' 0.066
0
112.0
0.034
0
168.0
0.063
2
41.2
0.020
376 .840 376 849 376 836 376 841 376 884 376 828 376 879 376 868
ii i *
> 1
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Figure CONCENTRATION OF OR' EXPONENTIAL FUNCTION O
NE IN BLOOD AS AN CONCENTRATION IN AIR
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FIGURE 2
CONCENTRATION OF ORGANIC FLUOR:INE IN BLOOD VS.
THE SQUARE ROOT OF
CONCENTRATION IN AIR.
p r!
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FIGURE 3 A FIRST-ORDER PLOT OF PERFLUOROOCTANOIC ACID
ELIMINATION FROM BLOOD
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000G80
t
i A FIRST ORDER PLOT
/
SAf & 4 0 O & j
ELIMINATION FROM BLOOD I
_ --
- . / ' ......'m:'
r, s+ jp f
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FIGURE 5 THE ELIHINATION RJyTE OF AS A FUNCTION OF ITS CONCEN
LOOD |
)
y+ ,/
.......... > ...*........'............../...... ........................*........................*............................*...... ... ' . ~ * /0o
*4 c o * i/r* CO*C. ^ / > u c a o
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"A i / ---------------
FIGURE 6 c
f
THE ELIMINATION RATE OF PERFLUOROOCTANOIC ACID
AS A rUNCTION OF 1TS CONCENTRATION IN BLOOD.
I I
7
#
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FIGURE 7 RELATED FLUORINE IN BLOOD AS A FUNCTION OF TIME SA* & O 0 >
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III. REFERENCES
1. D. R. Taves, Nature, 217, 1050 (1968). 2. K.: S, Guy. D. R. Taves, and W. S, Brey,
Aro.Chero.Soc.Symp.Ser-28, 117 (1976). 3. F, A. bel. s. 0. Sorenson.and D. E. Roach,
Am.Ind.Hyg.Assoc,J .. 41. 584, (1980). i 4. B. Kissa, Anal.Chem, 55, 1445 (1983). 5. E. Kissa, Clin. Chero. 33., 253 (1987). 6. E. Kissa, CP-Jl-80-14 (I960), 7. R. H. Ophaug and L, Singer, Froc. Soc. Eatp. Biol. Med.
163. 19 (1980). 8. J . ,Bel isle and D. F. Hagen, Anal. Biochem, 101, 369 (1980).
Submitted for Approval: Sent for Patent Approval:
Sent for Recording: Date to Typist: Date Typed:
EKijve CP-JL-87-5 0074J
i
12/9/86 3/24/87
.12/9/86 12/9/86 2/17/87
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PUBLICATIONS E. Kissa
. BOOKS
j.
: i
W. 0. Cutlet and . Kissa, Editors. "Detergency. Theory and
Technology". Marcel Dekker. New York (19861.
BOOK CHAPTERS
Erik Kissa -- Evaluation of. Detergency, pp. 1 to 89, in "Detergency. Theory and Technology", W. G. Cutler and E. Kissa eds., Marcel Dekker, New York (1986).
Erik Kissa Kinetics and Mechanisms of Soiling and Detergency, pp, 193 to 331, in "Detergency. Theory and Technology". W. C. Cutler and E, Kissa eds., Marcel Dekker, New York (1986).
Erik Kissa Soil Release, pp. 333 to 369, in "Detergency. Theory and Technology", W. G. Cutler and K. Kissa eds,, Marcel Dekker, New York (1986),
Erik Kissa -- Repellent Finishes, pp, 143 to 210, in "Handbook of Fiber Science and Technology", Vol. 2, M. Lewin and S. S, Sello, eds., Marcel Dekker, New York (1984).
Erik Kissa - Soil Release Finishes, pp. 211 to 289. in "Handbook of Fiber Science and Technology", Vol. 2, M. Lewin and S. S. Sello, eds.. Marcel Dekker, New York (1984).
Erik Kissa Quantitative Analysis, pp, 619 to 653, in "The Analytical Chemistry of Synthetic Dyes", K. Venkataraman, ed., Wiley-lnterscience, New York (1977),
JOURNAL ARTICLES
* Erik Kissa Single author, unless noted otherwise.
Determination of Inorganic Fluoride in Blood, Clin. chem., 32, 253 (1987).
Determination of Organofluorine in Air, Environm. Science Technol.. 20, 1254 (1986).
Tinctorial Efficacy of Dyes and Dyeing Processes. Colourage Annual. 1984-85.
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if
OQOs&y
V M Ojj> . Kissa
JOURNAL ARTICLES (Confd.)
Determination of 2H-hexafluoroptopanol-2 in Air- J. Chromatography. 319. 407 (1985).
Soil Release - Past. Present, and Future, Colour age Annual, Colour Publications (Bombay, India), (1984).
Tinctorial Efficacy of Dyes in Polyester Fibers. Textile Res. J.. 54, 497 (1984).
Determination of Fluoride at Low Concentrations with the Ion-Selective Electrode. Anal, Chem., 55, 1445 (1983).
Determination of Hexachloroacetone in Air, Anal. Chem., 5*>, 1222 (1983).
Determination of Trace Amounts of Sulfur in Organic Solvents,
Anal. Chem.. 4 *4*0 (1982).
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A. M. Dave and E, Kissa, A Rapid and Reproducible Transfer
Soiling Method. Textile Res. J,, JjJk. 650 (1981).,
Mechanisms of Soil Release, Textile Res, J., 51 508 (1981).
Wetting and Detergency, J. Pure and Applied Chemistry (1UPAC) 53, 2255 (1981).
Capillary Sorption in Fibrous Assemblies. J. Colloid and Interface Sci.. 83., 265 (1981).
A. M. Dave and E. Kissa. Comparative Studies of Two Soiling Methods. Textile Chem. Color. 12, 255 (1980).
Deterrainat ion of Disperse Dyes in Polyethylene Terephthalate Fibers. Textile Research Journal, 9, 245 (1979).
Kinetics and Mechanisms of Detergency III. Effect of Soiling Conditions on Particulate Soil Detergency. Textile Research
Journal 49, 384 (1979),
Kinetics and Mechanisms of Detergency II. Particulate Soil. Textile Research Journal 48. 395 (1978).,
Determination of Cationic Dyes in Acrylic Fibers, Textile Chem Col. , 148 (1977),
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E. Kissa
JOURNAL ARTICLES (Cont'd.)
Quantitative Determination of Dyes in Textile Fibers IV. Determination of Disperse and Cationic Dyes in Polyester Fibers by Selective Extraction, Textile Res. J. 46, 483 (1976).
Erik Kissa and Robert H, Dettre, Sorption of Surfactants In Polyester Fibers, Textile Res. J. 5, 773 (1975).
Kinetics and Mechanisms of Detergency I. Liquid Hydrophobic (Oily) Soils, Textile Res. J. 45. 736 (1975).
, ' J Quantitative Determination of Dyes in Textile Fibers III, Cationic Dyes in Polyester and Polyacrylic Substrates, Textile Res. J. 45. 488 (1976).
Quantitative Determination of Dyes in Textile Fibers II. Nonionic Dyes in Polyester. Polyamide, Acrylic, Acetate and Cellulosic Substrates, Textile Res. J. 45, 290 (1975),
Quantitative Determination of Dyes in Textile Fibers II. Nonionic Dyes in Polyester, Polyamide. Acrylic, Acetate and Cellulosic Substrates, Textile Res. J. 4J5, 290 (1975).
Quantitative Determination of Dyes in Textile Fibers 1, Cationic and Nonionic (Disperse) Dyes in Polyacrylonitrile Polymers, Textile Res. J. 44. 997 (1974).
Comments on Soil Release Mechanism of Acrylic Polymers, Textile Chem. COl, 5, 232 (1973).
Model Particulate Soils for Soil Release Evaluation. Textile Chem. Col. 5, 250 (1973).
Adsorption of Particulate Soils on Textiles, Textile Res. J. 45, 86 (1973)
Kinetics of Oily Soil Release, Textile Res, J. 41, 760 (1971).
A Reproducible Method for the Evaluation of Sail Release, Textile Chem. Col. 3., 225 (1971).
A Rapid and Reproducible Method for the Determination of Dry Soil Resistance, Textile Res. J. 41, 621 (1971).
Lightfastness of Reactive Dyes, Textile Res. J. 4JL, 715 (1971).
Urea in Reactive Dyeing, Textile Res. J. 3j), 734 (1969)..
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000689
r..' L . AT IONS
E. Kissa
| JOURNAL ARTICLES {Confd.)
Therroofixation of Vinylsulfone Type Reactive Dyes on Cotton, Amec. Dyeat. Rep. 56., 106 (1967).
Erik Kissa and Mairau Seepere-Yllo, Tungsten Trioxide and *1 j
Inorganic Salts as sample Additives in Carbon and Hydrogen
Anal/sis, Hikcochem, Acta 1967, 287.
* '! L
Conductivity Anomalies of Dimethyl Sulfone, J. Electroehem.
SOC. 111. 716 (1965). i
I
Solutions of Alkali Metal Carboxylate Mixtures in Hydrocarbons;
J. Colloid Science ii. 279 (1964).
Solubilization of Lithium Cacboxylates with Carboxylic Acids in
Hydrocarbon Solvents, J. Colloid Science xe, 147 (1963).
}
i
Solubility of Alkali Metal carboxylates in Hydrocarbons, J.
Colloid Science 7, 857 (1962).
The Isolation of Microbalances Against Vibrations, Mierochem.J. 4, 89 (1960).
The Mierodetermination of Carbon and Hydrogen in Compounds
Containing Alkali and Alkaline Earth Metals, Mierochem.J.1, 203 (1957).
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INVITED PAPERS PRESENTED
Erik Kissa -- single author* unless noced otherwise.
Determination of Organofluorine in Air, 190th American Chemical Society National Meeting, Chicago, 111., Sept. 1985.
Wetting and Detergency, 186th American Chemical Society National Meeting, Washington, D.C., Aug. 1983.
Mechanisms of Soiling and Detergency, Soil Release Finishes. Evaluation of Detergency: Natural and Model Soils, Visual and Spectrophotometric Soil Evaluation. Conference on Soiling and Detergency, Clemson University. February 1983.
i
Wetting and Detergency. (Topical lecture.) The Fourth International Conference on Surface and Colloic Science, Jerusalem, July 1981. (Sponsored by IUPAC).
Evaluation of Detergency, American Oil Chemists Society Annual Meeting, New Orleans, May 1961.
Capillary Sorption in Textiles. Second Chemical Congress of the North American Continent incl. the 180th ACS National Meeting, Aug. 1980. Symposium on Reactions at Fiber surfaces, has Vegas.
A, M. Dave and Erik Kissa, Dry Soiling and its Prevention, Multinational Symposium on Cotton Finishing, sponsored by UNIDO. ACS/CSJ Chemical Congress in Honolulu, Hawaii. April 1979.
Mechanisms of Soil Release. Multinational symposium on Cotton Finishing, sponsored by UNIDO. ACS/CSJ Chemical Congress in Honolulu, Hawaii, April 1979.
Kinetics of Detergency. Particulate Soils, 174th ACS National Meeting, Chicago, 111., Aug. 1977.
Soiling and Detergency, Gordon Research Conference, Textiles:
Fiber Science, 1975.
i
Sorption of Surfactants in Polyester Fibers, 169th ACS National Meeting. Philadelphia, Pa,, April 1976.
Kinetics of Detergency, 168th ACS National Meeting, Atlantic City. N.J., Sept. 1974.
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000691
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U.S. PATENTS ISSUED
Erik Kissa
1961
US 3 013 869 : Hydrocarbon soluble alkali metal . : : compositions
1965
US 3 184 28*
Dye-pad, hot-chemical-treatment dyeing process j
1966 iUS 3 290 282 Ii
1967 US 3 313 797
Fiber-reactive dyes Stabilized fiber-reactive dyes
1967 US 3 321 457
Water soluble dyes of the phenylazopyrazolone series containing a
2,3-dichloro-6-quinoxalinylcar bonylamino substituent
1969
US 3 463 038 Compartmented electrochromic device fCoinventors P. Manos and C. Wahlig)
1970
US 3 507 850
Polymeric fugitive dyes derived from methacrylate alkyl ester, methacrylic acid and ,a dye monomer containing sulfonic acid groups and a methacryloyl group {Coinventor W. Cohen)
1972
US 3 660 008
Dyeing sulfonated anionic polymeric fibers with an aqueous dispersion of a salt and an arylsulfonate
1973
US 3 765 835
Anionic dispersion of a salt of a cationic dye and a selected arylsulfonate
1973 t
1977
US 3 778 226 US 4 063 889
Durable-press and soil-release compositions
Halosolvent dyeing process for polyester with cationic dyes having sulfosuccinate anions.
- 27
!
000692
JACKSON LABORATORY. CHEMICALS AND PIGMENTS DEPARTMENT
RESEARCH AND DEVELOPMENT ANALYTICAL -- SPECTROSCOPY AND PHYSICAL TESTING
SSBLMf
1 2! 3 4
Author Sr. Research Supervisor Laboratory Manager Research Director
5-6 7-10 11
Research Supervisor
E. Kissa
C. J* Hens1er
J. P, Jesson
C. E. Lorenz) In 1j
N, E. Krause) Turn .
Central Report- Index
Jackson Laboratory Piles
H. F. Wyles
. j'
/jve 007 3J
{
t
000 6 9 3
