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Ce: S. Korzeniowski - DuPont M. Dominiak - U.S. EPA
P U > . Chemical Solutions Enterprise
P. O. Box 80023, BMP 23-1324 Wilmington, DE 19880-0023
OPPT Document Control Office EPA East, Room 6428 1201 Constitution Avenue, NW Washington, D. C. 20460
February 12, 2002
To Whom It May Concern:,
Please find enclosed an updated copy o f the DuPont presentation submitted to the Agency at the meeting held on December 17, 2001. The CBI claim for the information on pages 21 and 66 is withdrawn. These pages contain no CBI and should be included in the public record. Text has been added to pages 21 and 66 to clarify that the proposed timelines are subject to change and harmonize the study material names with those used throughout the balance o f the document. Otherwise, these pages do not differ in any other way from the documents that were provided on December 17, 2001. The non-CBI version o f this document is intended to replace the previous version (AR226-1042) in the public record.
Please contact me if you have any questions regarding this submission.
Robert C. Buck, Ph.D. Sr. Technology Consultant
Phone: 302.892.8935 Fax: 302.892.1124 Email : robertc.buck@usa.dupont.com
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4 V)S
17 Dec. 2001
DuPont Product Stewardship Update
United States Environmental Protection Agency
17 December 2001
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R. C. Buck, G. L. Kennedy, S. H. Korzeniowski, J. C. Stadler
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Discussion Outline
17 Dec. 2001
Reconnect to 21 Feb Discussion
Work Plans & Chemistry, Radio-label
Toxicology
- Biopersistence - Repeated Dose, Reproduction & Developmental Studies - Structure - Activity Relationships
Exposure Connection : What the data means
- Human Exposure : Worker Data, Consumer - Environmental Exposure
Environmental Fate & Effects
- Physical - Chemical Properties - Environmental Fate - Environmental Effects
Conclusions Discussion
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17 Dec . 2001
CBI Information has been redacted
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DuPont Fluorotelomer Product Groups:
Intermediates, Surfactants, Polymers
1) Intermediates
Sales Products
CF2=CF2
(TFE)
I
F(CF2CF2)nI
I
(Telomer A)
n = 2-8
F(CF2CF2)nCH2CH2I (Telomer B)
2) Surfactants / " M olecules' * \m o n ic - Phosphate C aihuxylait..
Nuilonale
* Nom onic Ethoxviate * Hclailk:
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F(CF2CF2)nCH2CH2OH (Telomer BA)
I Straight Chain Alkyl
F(C F 2C F 2)nCH2C H2O C (0 )C (R )= C H 2
3) Polymers Acrylic
Ester Amide Urethane Urea
Zonyr* T M (r = c h 3) ; Zonyl*
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Synthetic Strategies for Radiolabeled Fluorotelomers
17 Dec. 2001
FF
C7F 15'^*'''''^''OH
November 2001 DCSE R&D
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General Synthetic Strategy
17 Dec. 2001
- practical synthesis not demonstrated; SHE issues
Must use readily available sources of 14C
- e.g., C 0 2 (ex. B aC 03), NaCN, etc. - ample literature precedent for conversion o f C = 0 into CF2 - typical reagents: Et2NSF3 (DAST); (MeOCH2CH2)2NSF3 (DeoxoFluor)
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Radio-label Synthetic Routes
17 Dec. 2001
Multiple (5+) Deoxyfluorination routes explored using different starting synthons
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Successful Synthetic Route
17 Dec. 2001
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Synthetic Route provides access to a ll the key Fluorotelomer Intermediates : Telomer A, Telomer B and Telomer BA
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Product Stewardship Analysis
17 Dec. 2001
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Toxicity Studies
Acute Toxicitv
Oral, Inhalation Eye, Skin Irritation Skin Sensitization
17 Dec. 2001
Repeat Dose Toxicitv
Oral, Dermal Inhalation (AEL)
Basic evaluation set
Genetic Toxicitv
Expanded evaluation
Developmental Toxicitv
ReDroductive Toxicitv
Pharmacokinetics
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17 Dec. 2001
Summary : in Vivo Biopersistence Screening of Fluoro-
Organic Chemicals in Male Rats Purpose : To compare bio-uptake and bio-clearance in rat blood for a
series of fluorotelomer intermediate, surfactant and polymeric products including PFOS as a positive control. S tu d y : 10 consecutive days dosing via oral gavage, 84 day recovery period with analysis of total Blood, Liver & Fat fluorine on selected days (3 during dosing, 4 during recovery). Analysis : Use fluorine data to compare internal exposure of fluoroorganic materials on a dose normalized or prnolar basis.
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17 O ec. 2001
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17 Dec. 2001
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17 Dec. 2001
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17 Dec. 2001
Biopersistence Studies - Key Learnings
Telomer-based materials do not act like PFOS in the blood or liver - Blood total fluorine AUC's much lower than PFOS - Liver total fluorine lower than PFOS
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Repeated-Dose Study Plans
90 Dav Subchronic Study
Determine systemic effects from repeated oral gavage exposure
17 Dec. 2001
One-Generation Reproduction Study
Determine effects on parental capability to conceive, bear offspring and evaluate effects on offspring during pregnancy, early feeding and maturation to adulthood
Developmental Toxicity Study
Determine effects on fetal development (I.e. growth, maturation, abnormalities)
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90 Day Repeated Oral Dosing & One-Generation Reproduction Study
Dose Levels :
three levels + control
Experimental A nim al: Male & Female CD Rats
Study Evaluations :
90 Dav Repeated Dose :
appearance, behavior, weight, blood, organs and tissues, (3-oxidation
U.S. EPA Health Effects Test Guideline : OPPTS 870.3100 (1998)
Reproduction :
Adult In life : body wt., clinical signs, limited histopathology, female reproductive cycle time, sperm assessment, reproductive organs, mating, fertility;
Pups: physical development and maturation to adulthood, reproductive organs
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90-day & One-Generation Reproduction Study Protocol
J1 s
gi
Pretest " %
90-day Dosing Period
Repeat Dose Toxicity
:i i i sm l
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Pi
10 anima Is/sexydose
ip. Pretest
30 Day Recovery
90-day Dosing Period
|H !I
N
i o
One Month io
2 Recovery 2
10 animals/sex In control and high dose
Reproductive Evaluations
Pretest
P1 Adult Dosing Period
r VaginalS. ' Mating/Gestation/lactetion
. -i. .1! -- 'i1.!.. .1....... '...........'.I
O
" F1 Adult <3 Evaluations
Developmental Landmarks
20 animals/sex/dose
Feces
90 Day Recovery
Pretest 90-dav Dosing with Blood Collection
........ '1|1' 'n ""1.....
iwne
all
90-dav Recovery with Blood Collection
& Blood Fluorine
- "r.$..s" "7r IH
"8 SB---5-- sr Q33 S
5 animals/sex/dose
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Developmental Study
17 Dec. 2001
Dose Levels :
Three Doses + Control
Experimental A nim al: Male & Female CD Rats
U.S. EPA Test Guidelines : 870.3700; OECD Sect. 4, No. 414
Stud\ Evaluations ;
Determine effects on fetal development (I.e. growth, maturation, abnormalities)
M aternal: clinical signs, body weight, gross pathology
Pup: sex, body weight, external, skeletal and visceral examinations
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17 Dec. 2001
DuPont Toxicology Studies Timeline*
120001 21 | 22
Test M aterial Telomer Urethane Polymer Telom er Alcohol Interm ediate
Telomer Ethoxylate
Telomer Phosphate
Telomer Acrylate Polymer
Work
90 Day Oral Repeat Dose + tGen Repro (Rat)
Developmental Study (F i 90 Day Ranae-Findinq Study
JH
90 Day Oral Repeat Dose + 1Gen Repro (Rat)
Developmental Study Rangefinder
Genetic Toxicity: In Vitro Chrom Ab
Developmental Study
90 DayRanqe Finding
90 Day Oral Repeat Dose,1 Gen Repro (Rat)
Developmental Study Randetinder
Developmental Study
Ranqe Findinq
90 Day Oral Chronic Repeat Dose (Rat)
1Gen Reproduction Study (Rat)
Developmental Study
Ranqe Findinq
Developmental Study
90 Day Oral Repeat Dose, 1Gen Repro (Rati
HH rzr z
il rt
1 1p r
m
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Multiple Compounds Biopersistence Gavage Screen #2 Intermediate, Surfactant and Polymer
I
* This is a proposed timeline and subject to change.
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Telomer BA Synthesis Chemistry
CF2=CF2
(TFE)
lF(CF2CF2)nI (Telomer A)
n=3-6
17 Dec. 2001
F(CF2CF2)nCH2CH2I (Telomer B)
F(CF2CF2)nCH2CH2OH Telomer BA
Straight Chain Alkyl
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Actual Telomer BA Study Material Com position
C4 C6 C8 CIO C12+
F(CF2CF2)nCH2CH2OH Chain Length n= Number
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17 Dec. 2001
Telomer BA : Repeated-Dose Toxicology Information F(CF2CF2)nCH2CH2OH n= 3 -6
Repeated Dose Toxicity : NOEL 25 mg/kg/day
Reproductive Toxicity : NOEL 25 mg/kg/day
Developmental Toxicity : NOEL 200 mg/kg/day
Genetic Toxicity :
Negative AMES, Chrom Ab
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Telomer BA : 90 Day Study Results
Study Conclusion: NOEL = 25 mg/kg/day
17 Dec. 2001
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17 Dec. 2001
One-Generation Reproduction Study : F1 Survival Indices
/ if
tf *
*
/
Lactation
JL
'4' P
1
17 Dec. 2001
Telomer BA : Reproduction Study Results
Study Conclusion: NOEL = 25 mg/kg/day
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17 Dec. 2001
Telomer BA : Developmental Study Results
Study Conclusion: NOEL = 200 mg/kg/day
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Telomer BA : Study Conclusions
Subchronic - Primary adverse target is teeth (fluoride) - Other compound-related effects were non-adverse physiological responses : liver, kidney, thyroid
Reproduction - not a selective reproductive toxin
Developmental - not a selective developmental toxin
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Telomer Ethoxylate : Chemistry
17 Dac.2001
F(CF2CF2)nCH2CH2OH
i
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F(CF2CF2)nCH2CH20(CH2CH20 )xH*
Product by Process Mixture of Mixtures : Fluorocarbon Chain and EO Chain are both
gaussian distributions and tailored for specific end-uses
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17 Dec . 2001
Telomer Ethoxy late : Repeated Dose Toxicology Information
Repeated Dose Toxicity: NOEL 50mg/kg/day
Reproduction :
Pj NOEL = Not Established
Fj NOEL = 25 mg/kg/day
Developmental Toxicity: NOEL 50mg/kg/day
Genetic Toxicity:
negative AMES
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17 Dec. 2001
Telomer Ethoxylate : 90 Day Study Results
Studv Conclusion: NOL = 25 mg/kg/day
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17 Dec. 2001
Telomer Ethoxylate : Reproduction Study Results Study Conclusion: P, NOEL = Not Established
NOEL = 25 mg/kg/day
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17 Dec. 2001
One-Generation Reproduction Study - P1
Fertility Index (%) = # Animals that Deliver Pups # Animals that Mate
Fertility Index accounts for any event from mating to birth.
Reduction may be due to lack of fertilization, implantation or embryo viability
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17 Dec. 2001
Telomer Ethoxylate : Developmental Study Results Study Conclusion : NOEL 50 mg/kg/day
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17 Dec. 2001
Telomer Ethoxylate : Study Conclusions
Subchronic - Primary adverse targets are red blood cell mass & kidney - Other compound-related effects were non-adverse physiological responses : liver, thyroid, spleen
Reproduction - pup (FI) effects occurred only at dose levels with systemic effects on blood and kidney
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Developmental - not a selective developmental toxin
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17 Dec. 2001
Telomer Phosphate Chemistry
F(CF2CF2),,CH2CH2OH ^
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[F(CF2CF2)nCH2CH20 ]xP(0)(0NR3H)3.x*
Products by Process BL, B Telomer Distributions tailored to end-use
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Telomer Phosphate : Study Update
17 Dec. 2001
90 Day Repeated Dose Oral Gavage Study - production material - In-life complete, histopathology evaluations ongoing
Reproduction & Developmental
- range-finder underway - studies to begin 1Q2002
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17 Dec. 2001
Telomer Urethane Polymer : Chemistry
F(CF2CF2)nCH2CH2OH (Telomer BA)
Telomer Urethane Polymer
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17 Dec. 2001
Telomer Urethane Polymer : Repeated Dose Toxicology Information
Repeated Dose Toxicity:
Reproductive Toxicity: Developmental Toxicity: Genetic Toxicity:
LOEL 50mg/kg/day (nose only)
No Observed Adverse Effect at 50 mg/kg/day for all other parameters
No effects on reproduction at any dose level No abnormalities or birth defects Negative AMES and Chom Ab
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17 Dec. 2001
Telomer Urethane P olym er: 90 Day Study Results Study Conclusions :
NOEL Not Established N o O bserved A dverse E ffect at 50 m g/kg/day for all other parameters
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17 Dec. 2001
Telomer Urethane Polymer : Reproduction Study Results Study Conclusion: NOEL = 50 mg/kg/day No effects on functional reproductive parameters at any dose level
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17 Dec. 2001
Telomer Urethane Polymer : Developmental Study Results Study Conclusions: Developmental NOEL = 250 mg/kg/day Maternal NOEL = 50 mg/kg/day
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17 Dec. 2001
Telomer Urethane Polymer: Study Conclusions
Subchronic - Primary adverse effect is nasal lesions - Other compound-related effects were non-adverse physiological responses : liver, thyroid
Reproduction - not a selective reproductive toxin
Developmental - not a selective developmental toxin
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17 Dec. 2001
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17 Dec. 2001
Fluorotelomers Exposure Assessment
In-Use Exposure Assessment Environmental Release Assessment
- Product Trails external focus : markets where used distribution, use, disposal
- Mass Balance Environmental releases & media (Land. Air, Water)
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: In-Use Exposure Model
17 Dec. 2001
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: In-Use Exposure Model
17 Dec. 2001
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: In-Use Exposure Model
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17 Dec. 2001
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Product Trails
For each Market / End-Use by Product Used to determine product release points
Product Trail : Carpet
17 Dec. 2001
Production
D IS T R IB U T IO N
USE
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DISPO SAL 5l
17 Dec. 2001
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Environmental Compartments
based on emissions assessment
17 Dec. 2001
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17 Dec. 2001
DuPont Environmental Fate & Effects Studies
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Study Materials
CBI Information has been redacted
17 Dec. 2001
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17 Dec. 2001
Physical - Chemical Properties
n-C8F17CH2CH2X, n-C6F13CH2CH2X X * OH, I
UV / Visible Absorption Spectrum Vapor Pressure Sorption Water Solubility Henry's Law Constant Log Kow Octanol - Water Partition)
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17 Oec. 2001
UV-Visible Spectra : Telomer B Alcohols & Iodides
No absorbance in visible light range, 350-800nm Direct photolytic degradation not expected Indirect Photolysis [OH Radical] work underway (8-2 Alcohol, TRP)
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Vapor Pressure : Telomer B Alcohols & Iodides*
Data fit to Antoine Equation extrapolated to ambient, 20C No anomalies observed
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Physical - Chemical Properties : Sorption 6-2, 8-2 Telomer B Alcohols & Iodides
17 Dec. 2001
rapid sorption from saturated aqueous solution - glass, silanized glass, plastic, PTFE, stainless steel
evidence o f time-dependent adsorption with decreasing ability to recover materialfrom surface(s)
specific recovery methods had to be developed and validated
- weeks for each sample to reach equilibrium with continuous analysis - 8 to 20 samples replicated to establish method and analysis confidence
makes water solubility measurement much more complicated and mass balances difficult to achieve
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Physical - Chemical Properties : Water Solubility 6-2, 8-2 Telomer B Alcohols & Iodides
17 Dec. 2001
pH 3, 7, 9 ; T = 12, 25, 37, 60C see no differences in solubility versus pH material is adsorbed to the container, not in the water, when
excess material is no longer present
- sorbed to the container surfaces
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Physical - Chemical Properties : Water Solubility 6-2, 8-2 Telomer B Alcohols & Iodides
17 Dec. 2001
CeFiaCHgCHgOH C8F 17CH2CH2O H CeFisCHaCHsI C8F 17CH2CH2l PFOA PFOS
Solubility ug / m L (ppm)
12C
25C
37C
60C
preliminary data 1 range
0.134 + 0.029 0.150 + 0.005 0.318 + 0.176
preliminary data : 0.1 range work ongoing
> wt 10 %
680
De-ionized water measurements
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Physical - Chemical Properties : Henry's Law Constant 6-2, 8-2 Telomer B Alcohols & Iodides
Computed from Water Solubility and Vapor Pressure Non-linearity and Non-traditional behavior Surface Tension Driving Behavior? Plan to Measure utilizing Static Headspace Method
(ref. J. D. Stuart, etal., Analytical Chemistry, 1993, 65.3113-3118)
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17 Dec. 2001
Physical - Chemical Properties : Conclusions 6-2, 8-2 Telomer B Alcohols & Iodides
Water Solubility varies with T but not pH and is in the range of 0.1 - 1.0 ppm Highly sorptive onto many surfaces and may remain highly sorbed and
difficult to remove Preliminary VP data do not exhibit anomalies No visible light absorbance
These properties present significant method development and analysis challenges going forward and will require use of radiolabeled material for more studies than expected
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17 Dec. 2001
Analytical : Method Development Challenges
Head-Space Analysis Method
- Parent and potential degradation product(s)
Extraction & Recovery Methods
- Matrices: Soil, Sediment, Sludge, Labware Surfaces, Water - Materials : Parent & Degradation Product(s), including radiolabel
Analysis Methods (GC/MS, LC/MS/MS)
- Parent & Degradation Product(s) in relevant matrices - Radiolabeled Materials (stop-flow scintillation counter)
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17 Dec. 2001
Environmental Fate & Effects Work Plan
f Environmental Fate : Abiotic Hydrolysis Adsorption / Desorption *
Physical Properties
UV/Visible Spectrum Water Solubility Adsorption to Glass Air-Water Partition
Coefficient
\
Environmental Fate : Biotic Anaerobic Biodegradation* Aerobic Biodegradation*
( * Radiolabeled M aterial)
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Environmental Effects Bioconcentration Screen
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17 Dec. 2001
DuPont Environmental Fate & Effects Timeline*
Test Materials
Work
8-2& 6-2 B. BA
P Physical Properties
Multiple Compounds
E Bioconcentration Factor (BCF)
htermediate, Surfactant and Screen (Minnow) I
Polymer
2001
2002
1Q2Q3QI4Q 1Q2Q 3Q 4Q
LI
1
Multiple Compounds
Bioconcentration Factor (BCF)
Intermediate, Surfactant and Screen (Minnow) II
Polymer
I I
8-2 Telom er Iodide C8F17CH2CH2I
"M odel" Urethane P o lym e r "M odel" Urethane P o lym e r "M odel" Acrylate P o lym e r
F Hydrolysis
F Adsorption / Desorption (14C) F Aerobic Biodegradation (14C) F Anaerobic Biodegradation (14C) F Hydrolysis
~ T a be Ion rirT M il flel vith
rsii oRc rwcn r t1
' rn --! I
F Anaerobic Biodegradation (14C)
"1
?! Hydrolysis
Work Underway
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17 Dec. 2001
Conclusions
DuPont fluorotelomer-based products are safe for their intended uses. - DuPont's data and analysis support this conclusion
DuPont fluorotelomer-based products do not have the same overall PBT properties as PFOS Chemicals
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17 Dec. 2001
DuPont Product Stewardship Summary
We are committed to and staying in the business. We are confident that our products are safe for their intended uses. We have programs in place to learn more about our products:
Toxicology, Environmental Fate & Effect, Exposure We are working together with industry members & groups We will continue to have an open &frequent dialogue with
Regulators, Customers, and Employees
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Reflections & Discussion Questions Path Forward
17 Dec. 2001
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