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Specialty Chemicals & Equipment

Environmental Status and Use of TelomerBased Fluorosurfactants

Bob Gilbert

Sales and Marketing Manager

Chemguard, Inc.

OUTLINE

ENVIRONMENTAL ISSUESHISTORY OF PFOA/PFOS ISSUESTELOMER BASEDFLUOROSURFACTANTSREACH REGULATIONS ANDREQUIREMENTS

FLUOROSURFACTANTCHARACTERISTICSFLUOROSURFACTANT APPLICATIONS



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What are the longterm prospects forfluorosurfactants in industrial

applications?

Due to the decision by 3M to withdraw their PerfluorooctylSulfonate (PFOS) based products from the market, the onlyviable products left are produced from Perfluoro Telomer.

Recently, Perfluorooctanoic Acid (PFOA) has also comeunder considerable fire.


ENVIRONMENTAL ISSUESWITH PFOS/PFOA BASED PRODUCTS

Why did 3M agree to phase out 90Perfluorooctyl (FC95, FC120, FC135,FC430, ETC.) Sulphonate (PFOS) basedproducts by 2003?

Data indicate PFOS chemicals are Persistent


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PFOS is a very stable chemical that does not

break down or degrade in the environment

Data indicate PFOS chemicals are Bioaccumulative

PFOS can build up over time; its half-life in

human blood may be about 4 years

Data indicate PFOS chemicals are Toxic

PFOS is only moderately toxic via acute oral

exposure; rat LD50 of 251 mg/kg

In repeat oral dose systematic and reproductive

toxicity studies, however, serious effects are seen

Post-natal deaths in rats at 3.2 and 1.6 mg/kg/day In repeat-dose treated Rhesus monkeys, death within

3 weeks at 10 mg/kg/day; within 7 weeks at 4.5 mg/kg/day.


Comparison :Telomerization vs. ECF IntermediateProducts


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Telomerization (Fluorotelomers)

CF2= CF2 (TFE)

F(CF2CF2 )nI (Tel A)

F(CF2CF2 )nCH2CH2I (Tel B)

F(CF2CF2 )nCH2CH2OH (Tel BA)

Sales Products

Straight Chain Alkyl

ECF (ElectroChemical Fluorination)

C8H17SH

C8H17SO2Cl

C8F17SO2F

(POSF)

C8F17SO2X

Neutralize

(PFOS)

C8F17SO2N(C2H5)CH2CH2OH

30% Branched Alkyl) (N-EtFOSE)

Sales Products


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What are the longterm prospects forfluorosurfactants in industrial

applications?

Telomer manufacturers have been required to do largequantities of research on the environmental properties andfate of Perfluoro Telomers.

To date, this research has indicated that Perfluoro Telomers,although Persistent, do not appear to Bioaccumulate or beToxic as was PFOS. A positive result!


ENVIRONMENTAL ISSUESWITH TELOMER BASED PRODUCTS

Why does Chemguard see Telomer BasedFluorosurfactants safe from EPA’s actionin the near future?

In October 2003, the EPA Telomer Technical Workgroupdetermined that telomer-based AFFF fire fighting foam is notlikely to be a source of PFOA in the environment and will nothave to be tested in the current enforceable consent


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agreement (ECA) process.

The EPA has concluded that existing data “provided noevidence that these fluorosurfactants (C6 perfluoro- telomer)biodegrade into PFOA or its homologs…”

The March 2005 Fire Fighting Foam Coalition (FFFC) states“there is no known pathway for the C6 fluorosurfactants usedin AFFF to breakdown into PFOA.”


Chemguard uses the same fluorochemicalintermediate for the coatings, wetting andleveling market for as AFFFs!


Telomer based fluorosurfactants do notcontain PFOA, PFOS or any of itsderivatives or breakdown products.

REACH REGULATIONS FOR EUROPE

REACH is the new European Community(EU) regulation governing the “Registration,Evaluation, Authorization and restriction of


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CHemicals” It came into force on June 1st 2007 and replaces multipleEuropean directives and legislation with a single regulation.All EU members are required to enforce it.

Its primary aim is to protect human health and theenvironment.

REACH will have major impact on the entire chemicals sectorsince manufacturers and importers of chemical substancesmade in or imported into the EU in annual volumes of 1 ton ormore must register them with the European ChemicalsAgency (ECHA). It is estimated that more than 30,000 substancesindustry-wide will be affected by REACH.



REGISTRATION TIMELINE

PRE-REGISTRATION: JUNE 1, 2008- DECEMBER 1, 2008

REGISTRATION: 3 PHASES DEPENDING ON VOLUME IMPORTED


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1-100 TONS PER YEAR: JUNE 1, 2018

100-1000 TONS PER YEAR: JUNE 1, 2013

1000 TONS PER YEAR: NOVEMBER 30, 2010

REACH requires manufacturers and importers of chemicalsubstances to obtain information on the physico-chemical,health and environmental properties of their substances anduse it to determine how these substances can be used safely. Each manufacturer and importer must submit a registrationdossier documenting data and assessments. If substances are not registered correctly in time, they cannotbe manufactured, imported or sold.



EVALUATION PROCESS

Dossier evaluation - ECHA decides whether REGISTRATIONinformation complies with requirements and examines testingproposals made by registrants. Substance evaluation – ECHA in coordination with thecompetent authorities of the Member States assesses therisk of substances to human health or the environment anddetermines the possible need for additional informationand/or proposes further testing.


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AUTHORIZATION PROCESS

Companies applying for authorization must demonstrate thatany risk associated with uses of a substance is adequatelycontrolled or that the socio-economic benefits of useoutweigh potential risk.

Restriction The EU can impose restrictions and prohibit or set conditionsfor the manufacture, placing on the market or use of certaindangerous substances when unacceptable risks to humansor the environment have been identified.



BOTTOM LINE


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It will cost more to sell into the EU and this law will likelyspawn similar laws in other countries.

It is likely many chemicals will be discontinued due to the costof testing.



MORE INFORMATION

REACH USA 2008

April 15-17 2008, Boston, Massachusetts, USA

http://www.rapra.net/products_and_services/Conferences/REACH_USA_2008.asp


FLUOROSURFACTANTSMAJOR ADVANTAGES


Best known products for wetting


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Superior interfacial tension reductionwhich speeds up emulsionCan perform all vital surfactant jobsHigh cost can be offset by lower uselevels

Characteristics vital to useWetting abilityEmulsificationCorrosion inhibitionLeveling

Dispersing abilityFoamingPore penetrationAnti-blocking

FS8

FS7

FS6


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FS5

FS4

FS3

FS2

FS1

Product

Yes

No

95% or >

Slightly Cationic

Yes

No

95% or >

Slightly Cationic/Silicone

Yes

No

95% or >

Anionic/Silicone

No

Yes

95% or >

Nonionic

No

Yes


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> 50%

Nonionic

No

No

95% or >

Cationic

No

No

95% or >

Anionic

No

No

> 50%

Amphoteric

Mixture Y/N

Polymer Y/N

C6-perfluoro

Type

Fluorosurfactant Product Examples


Fluorosurfactant Product Examples



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35.4

26.6

21.6

85.0%

Polyoxyethylene - polyoxypropylene 15%

Polyalkyl ether fluorosurfactant

Nonionic

FS5

28.5

16.7

15.9

48.4%

Hexylene Glycol 9.5% water 39%

Blend of fluoro and silicone surfactants

Anionic/Silicone Blend

FS8

16.4

16.4

45%

Hexylene glycol 10% Water 55%

Blend of fluoro and silicone surfactants

Cationic/Silicone Blend

FS7

17.3


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16.2

45%

Hexylene glycol 10% Water 55%

Alkyl ammonium chloride fluorosurfactant Blend

Cationic Blend

FS6

34.3

24.6

21.2

45.0%

Isopropanol 34% alkyl polyoxyethylene 18% water 3%

Polyoxyethylene fluorosurfactant

Nonionic

FS4

55

46.6

28.6

30.0%

Hexylene Glycol 10% sodium chloride 3% water 57%

Alkyl ammonium chloride fluorosurfactant

Cationic

FS3

56.1

35.2


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19.9

45.0%

Hexylene Glycol 15% magnesium sulfate 1.7% water 38.3%

Alkyl sodium sulfonate fluorosurfactant

Anionic

FS2

35.7

21.3

21

25.0%

Hexylene Glycol 10% tetramethylene sulfone 3% water 62%

Alkyl amino acid fluorosurfactant

Amphoteric

FS1

(Actives Concentration)

(10ppm)

(100ppm)

(1,000ppm)

0.001%

0.01%

0.1%

Surface Tension (dynes/cm)*

Actives


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Solvent

Description

Type

Product

Name

KRUSS TENSIOMETER



Fluorosurfactants (FC) impart 10 to 100 times lowersurface tension than typical hydrocarbon


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Surfactants (HC) on water based solutions.

HC

FC

Chemguard Fluorosurfactant Product Line


X

X

X

-

X

X

X

-

X

S-222N

NONIONIC

X

X

X

-

-

X


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X

-

X

S-107B

NONIONIC

X

X

X

-

-

X

-

-

X

S-216A

CAIONIC

X

X

X

X

-

X

-

X

X


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S-208A

CATIONIC

X

X

X

X

-

X

-

X

X

S-106A

CATIONIC

X

X

X

X

-

X

-

-

X

S-228M

ANIONIC

X


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X

X

X

-

X

-

X

X

S-103A

ANIONIC

X

X

X

-

-

X

-

X

X

S-111

AMPHOTERIC

X

X

X

-


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-

X

-

X

X

S-100

AMPHOTERIC

ALKALIES

ACID

HEAT

STABLE IN

CORROSION INHIBITOR

ANHYDROUS

SOLUBLE IN POLAR SOLVENTS

SOLUBLE IN NONPOLAR SOLVENTS

FOAMING AGENT

WETTING AGENT

PRODUCT

TYPE

Chemguard Fluorosurfactant Product Line


0.5

-


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-

-

-

-

-

-

-

-

0.05

0.3

-

0.05

0.3

-

-

-

-

0.05

-

-

0.05

-

-

0.1


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-

FOAMING

Hydrocarbon Foamer

Aqueous Foamer

Acid (HCl) Foaming

0.05

0.05

0.05

0.1

0.1

0.1

-

-

-

-

-

-

-

-

-

-

-

-

-


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-

-

0.1

-

-

0.1

-

-

CLEANING

Alkaline Cleaners

Glass Cleaner and Defogging

Solvent Degreasing

0.05

0.05

0.05

0.1

-

0.1

0.1

-

-

-

-

-

-


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-

-

-

-

-

-

-

-

-

0.05

-

0.05

0.05

0.05

-

-

-

-

-

-

-

-

-

METALWORKS

Plating Bath Aid

Anticorrosion


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Cleaning and Scale Removal

Degreasing

0.05

0.05

0.05

0.05

0.1

0.1

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-


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-

-

-

-

-

GRAPHIC ARTS

Leveling

Wicking Decrease

Emulsion Wetting

0.05

0.05

0.05

0.05

0.1

0.1

0.05

0.1

-

0.05

0.1

-

0.05

0.1

-


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0.05

0.1

-

0.05

0.1

-

0.1

-

-

0.1

-

-

ADHESIVES

Wetting

Semi-Release Additive

Nonaqueous formulas

0.05

0.05

0.05

0.05

0.05

0.1

0.05


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0.05

-

0.05

0.05

-

0.05

0.05

-

0.05

0.05

-

0.05

0.05

-

0.1

0.1

-

0.1

0.1

-

PAINTS WAXES POLISHES AND COATINGS


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Wetting

Leveling

Antisoiling

S-222N

NONIONIC

S-107B

NONIONIC

S-216

CATIONIC

S-208

CATIONIC

S-106A

CATIONIC

S-228M

ANIONIC

S-103A

ANIONIC

S-111

AMPHOTERIC

S-100

AMPHOTERIC

PRODUCT

APPLICATION GUIDE

CONCLUSIONS


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Telomer based fluorosurfactants are saferthan PFOS/PFOA based products.Telomer based fluorosurfactants offersimilar characteristics to what the oldPFOS based products imparted toformulations.Concentrations can be low enough to makefluorosurfactants cheaper thanhydrocarbon surfactants for manyapplications.Lower concentrations equate to lessproduct ultimately released into theenvironment.

QUESTIONS?



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