IP Library Granted Patent US 9,029,452
Granted Patent B2
US 9,029,452 · App. 12/789,086 · Granted May 12, 2015

Fluoropolymer additive for coatings

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Quick Facts
Patent No.
US 9,029,452
App. No.
12/789,086
Granted
May 12, 2015
Kind
B2
Abstract

This invention relates to a composition comprising a solvent-based fluoropolymer and its use as a coating additive, and a coating composition comprising the fluoropolymer. The coating composition comprising the solvent-based fluoropolymer provides desirable properties including uniform spreading, and cleanability and increased contact angle to a coated substrate. There is further provided a method of treating a substrate using the coating composition.

Claims (64)

1. A coating composition comprising a fluoropolymer composition and a coating base, wherein the fluoropolymer composition comprises a fluoropolymer dissolved in an organic solvent and further wherein the fluoropolymer comprises repeating units in any sequence of polymer units:

(R f —X—Y—C(O)—CZ—CH 2 ) a —  I:

(R f —X—Y—C(O)—CH—CH 2 ) b —  II:

(CCl 2 —CH 2 ) c —  III:

(R 1 —O—C(O)—C(CH 3 )—CH 2 ) d —  IV:

(R 1 —O—C(O)—CH—CH 2 ) e —  V:

(R 2 —Y—C(O)—CT-CH 2 ) g   VI:

wherein

R f is C 6 F 13 —, and is a straight or branched alkyl, or a combination thereof;

X is an organic divalent linking group having from about 1 to about 20 carbon atoms, optionally containing a triazole, oxygen, nitrogen, or sulfur, or a combination thereof;

Y is O;

Z is a straight or branched alkyl group having from about 1 to about 4 carbon atoms, or halide;

R 1 is a straight or branched alkyl group having from 12 to 22 carbon atoms;

T is H, a straight, branched or cyclic alkyl group having from about 1 to about 10 carbon atoms, or halide;

R 2 is H, C n H 2n+1 , C n H 2n−1 , (CH 2 CH 2 O) p R 3 , (CH 2 CH(CH 3 )O) p R 3 , (C m H 2m )N(R 3 ) 2 ;

n is from about 8 to about 40;

m is 1 to about 40;

each R 3 is independently H, CH 2 OH or C q H 2q+1 ;

p is 1 to about 200;

q is 0 to about 40; and

provided that

1) repeating unit I, (R f —X—Y—C(O)—CZ—CH 2 ) a —, is present in the fluoropolymer at a minimum of about 30% by weight of the fluoropolymer,

2) repeating units I, II and III, (R f —X—Y—C(O)—CZ—CH 2 ) a —, (R f —X—Y—C(O)—CH—CH 2 ) b — and (CCl 2 —CH 2 ) c — are present at a minimum combined total of about 50% by weight of the fluoropolymer; and

3) the total of all repeating units, I-VI plus any optional monomers equals 100% by weight of the fluoropolymer,

wherein the subscripts a, c, and d are each independently from 5 to about 5,000 and wherein the subscripts b, e, and g are each independently from 0 to about 2,000,

wherein the organic solvent is methyl isobutyl ketone, butyl acetate, tetrahydrofuran, acetone, isopropanol, ethyl acetate, methylene chloride, chloroform, carbon tetrachloride, cyclohexane, hexane, dioxane, hexafluoroisopropanol, or a mixture of two or more thereof, and

wherein the coating base is selected from the group consisting of an alkyd coating, a Type I urethane coating, and an unsaturated polyester coating.

2. The coating composition according to claim 1 wherein g is a positive integer and R 1 is stearyl, CH 3 (CH 2 ) 17 .

3. The coating composition according to claim 1 wherein R 2 is an alkyl group containing 8 to 20 carbon atoms.

4. The coating composition according to claim 1 wherein the organic solvent is cyclohexane or methyl isobutyl ketone.

5. The coating composition of claim 1 further comprising an application solvent, which is selected from the group consisting of alcohols and ketones.

6. The coating composition according to claim 1 wherein the coating base is a solvent-based paint and the fluoropolymer composition is added to the paint in an amount of 0.001 weight % to about 1 weight % on a dry weight basis of the fluoropolymer to the weight of the wet paint.

7. The coating composition according to claim 6 wherein the fluoropolymer composition is added to the paint in an amount of 0.01 weight % to about 0.5 weight % on a dry weight basis of the fluoropolymer to the weight of the wet paint.

8. The coating composition according to claim 6 wherein the fluoropolymer composition is added to the paint in an amount of 0.05 weight % to about 0.25 weight % on a dry weight basis of the fluoropolymer to the weight of the wet paint.

9. The coating composition of claim 1 wherein R f is C 6 F 13 —, and is a straight or branched alkyl, or a combination thereof; R 1 is stearyl, CH 3 (CH 2 ) 17 ; R 2 is an alkyl group containing 8 to 20 carbon atoms; and the organic solvent is cyclohexane or methyl isobutyl ketone.

10. A method for treating a substrate with a coating composition comprising contacting the substrate with the coating composition and drying or curing the coating composition on the substrate, wherein the coating composition comprises a fluoropolymer composition and a coating base, wherein the fluoropolymer composition comprises a fluoropolymer dissolved in an organic solvent and further wherein the fluoropolymer comprises repeating units in any sequence of polymer units:

[R f —X—Y—C(O)—CZ—CH 2 ] a —  I:

[R f —X—Y—C(O)—CH—CH 2 ] b —  II:

[CCl 2 —CH 2 ] c —  III:

[R 1 —O—C(O)—C(CH 3 )—CH 2 ] d —  IV:

[R 1 —O—C(O)—CH—CH 2 ] e —  V:

[R 2 —Y—C(O)—CT-CH 2 ] g   VI:

wherein

R f is C 6 F 13 —, and is a straight or branched alkyl or a combination thereof;

X is an organic divalent linking group having from about 1 to about 20 carbon atoms, optionally containing a triazole, oxygen, nitrogen, or sulfur, or a combination thereof;

Y is O;

Z is a straight or branched alkyl group having from about 1 to about 4 carbon atoms, or halide;

R 1 is a straight or branched alkyl group having from 12 to 22 carbon atoms;

T is H, a straight, branched or cyclic alkyl group having from about 1 to about 10 carbon atoms, or halide;

R 2 is H, C n H 2n+1 , C n H 2n−1 , [CH 2 CH 2 O] p R 3 , [CH 2 CH(CH 3 )O] p R 3 , [C m H 2m ]N(R 3 ) 2 ,

n is from about 8 to about 40;

m is 1 to about 40;

each R 3 is independently H, CH 2 OH or C q H 2q+1 ;

p is 1 to about 200;

q is 0 to about 40; and

provided that

1) repeating unit I, [R f —X—Y—C(O)—CZ—CH 2 ] a —, is present in the fluoropolymer at a minimum of about 30% by weight of the fluoropolymer,

2) repeating units I, II and III, [R f —X—Y—C(O)—CZ—CH 2 ] a —, [R f —X—Y—C(O)—CH—CH 2 ] b — and [CCl 2 —CH 2 ] c — are present at a minimum combined total of about 50% by weight of the fluoropolymer; and

3) the total of all repeating units, I-VI plus any optional monomers equals 100% by weight of the fluoropolymer,

wherein the subscripts a, c, and d are each independently from 5 to about 5,000 and wherein the subscripts b, e, and q are each independently from 0 to about 2.000,

wherein the organic solvent is methyl isobutyl ketone, butyl acetate, tetrahydrofuran, acetone, isopropanol, ethyl acetate, methylene chloride, chloroform, carbon tetrachloride, cyclohexane, hexane, dioxane, hexafluoroisopropanol, or a mixture of two or more thereof, and

wherein the coating base is selected from the group consisting of an alkyd coating, a Type I urethane coating, and an unsaturated polyester coating.

11. The method according to claim 10 wherein the contacting step by brush, spray, roller, doctor blade, wipe, dip, foam, liquid injection, immersion or casting.

12. The method according to claim 10 wherein drying or curing step is performed by air curing, polymerizing, or energy curing.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2010
From: BROWN, GERALD ORONDE; MENG, XIANJUN
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 024683/0184 →