IP Library Granted Patent US 8,410,202
Granted Patent B1
US 8,410,202 · App. 13/280,088 · Granted Apr 2, 2013

Coating compositions

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Quick Facts
Patent No.
US 8,410,202
App. No.
13/280,088
Granted
Apr 2, 2013
Kind
B1
Abstract

A mixture of a functionalized polyfluoropolyether and a benzoxazine resin in a weight ratio of from about 1/99 to about 99/1.

Claims (44)

1. A composition consisting of a mixture of a functionalized polyfluoropolyether and a benzoxazine resin with the weight ratio of said functionalized polyfluoropolyether to said benzoxazine resin being from about 1/99 to about 99/1.

2. A composition consisting of a mixture of a functionalized polyfluoropolyether and a benzoxazine resin with the weight ratio of said functionalized polyfluoropolyether to said benzoxazine resin being from about 1/99 to about 99/1 wherein a solvent is present and is selected from the group consisting of methyl isobutyl ketone, methyl ethyl ketone, 1-butanol, xylene, N,N-dimethylformamide, N-methylpyrrolidone, tetrahydrofuran, toluene, hexane, cyclohexane, heptane, N,N′-dimethylacetamide, methylene chloride, and mixtures thereof.

3. A composition in accordance with claim 1 wherein the functionalized polyfluoropolyether is at least one of

R 1 —(—CF(CF 3 )—CF 2 —O—) n —R 2

R 1 —(—CF 2 —CF 2 —CF 2 —O—) n —R 2

R 1 —(—CF 2 —CF 2 —O—) n —(—CF 2 —O—) m —R 2

and

R 1 —(—CF 2 —CF(CF 3 )—O—) n —(—CF 2 —O—) m —R 2

wherein n and m each represents the number of repeating groups; n is from about 3 to about 120; m is from about 5 to about 120, and the sum of n and m is from about 40 to about 180; R 1 and R 2 are independently represented by A 1 —CF 2 O— and —CF 2 —A 2 , respectively, and A 1 and A 2 are independently at least one of

—A k —OH

—CH 2 (OCH 2 CH 2 ) p OH

—CH 2 OCH 2 CH(OH)CH 2 OH

—COOR H

—A k —Si(OR H ) 3

and

—A k —OP(O)(OH) 2

wherein A k , depending on the valences, is a chemical bond or an alkylene group with from about 1 to 10 carbon atoms; R H is H, or an alkyl group with from about 1 to about 10 carbon atoms, and p is from 1 to about 20.

4. A composition in accordance with claim 1 wherein the functionalized polyfluoropolyether is one of a hydroxyl terminated polyfluoropolyether, a carboxyl acid or an ester terminated polyfluoropolyether, a silane terminated polyfluoropolyether, and a phosphoric acid terminated polyfluoropolyether.

5. A composition in accordance with claim 1 wherein the benzoxazine polymer is at least one of

6. A composition in accordance with claim 1 wherein the benzoxazine is

7. A composition in accordance with claim 1 wherein the weight average molecular weight of the polyfluropolyether is from about 200 to about 3,000, and the number average molecular weight thereof is from about 100 to about 2,000 as determined by GPC analysis.

8. A composition in accordance with claim 1 wherein the weight average molecular weight of the benzoxazine is from about 450 to about 3,000, and the number average molecular weight is from about 400 to about 2000 as determined by GPC analysis.

9. A composition in accordance with claim 1 wherein said weight ratio of said functionalized polyfluoropolyether/benzoxazine resin is from about 20/80 to about 80/20.

10. A composition in accordance with claim 1 wherein said polyfluoropolyether is

HOCH 2 OCF 2 (CF 2 CF 2 CF 2 O) n CF 2 CH 2 OH

or

HOOCOCF 2 (CF 2 CF 2 CF 2 O) n CF 2 COOH

wherein n represents the number of repeating groups, and is a number of from about 3 to about 25.

11. A composition in accordance with claim 1 wherein said polyfluoropolyether is

HOCH 2 OCF 2 (CF 2 CF 2 CF 2 O) n CF 2 CH 2 OH

wherein n represents the number of repeating segments.

12. A composition in accordance with claim 3 wherein m is from about 10 to about 100, n is from about 10 to about 100, and A 1 and A 2 are independently one of —CH 2 OH or —COOH.

13. A composition in accordance with claim 3 wherein m is from about 20 to about 80, n is from about 20 to about 80, and A 1 and A 2 are —CH 2 OH.

14. A composition in accordance with claim 1 wherein said polyfluoropolyether is at least one of a hydroxyl terminated polyfluoropolyether, a carboxyl acid terminated polyfluoropolyether, an ester terminated polyfluoropolyether, a silane terminated polyfluoropolyether, and a phosphoric acid terminated polyfluoropolyether, and said benzoxazine is

or

15. A composition in accordance with claim 1 with a water contact angle of from about 90° to about 150°, and a hexadecane contact angle of from about 45° to about 95°.

16. A composition in accordance with claim 1 that possesses both hydrophobic and oleophobic characteristics, and a water contact angle of from about 95° to about 130°, and a hexadecane contact angle of from about 55° to about 80°.

17. A composition consisting of a mixture of a functionalized polyfluoropolyether and a benzoxazine resin with the weight ratio of said functionalized polyfluoropolyether to said benzoxazine resin being from about 20/80 to about 80/20, wherein said polyfluoropolyether is

HOCH 2 OCF 2 (CF 2 CF 2 CF 2 O) n CF 2 CH 2 OH

or

HOOCOCF 2 (CF 2 CF 2 CF 2 O) n CF 2 COOH

wherein n represents the number of repeating groups and which composition has a water contact angle of from about 95° to about 130°, and a hexadecane contact angle of from about 45° to about 95°.

18. A composition in accordance with claim 17 wherein n is a number of from about 3 to about 25 in said polyfluoropolyether and said benzoxazine is

or

Assignments (11)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
RELEASE OF SECURITY INTEREST IN PATENTS AT R/F 062740/0214 Recorded May 18, 2023
From: CITIBANK, N.A., AS AGENT
To: XEROX CORPORATION
Reel/Frame 063694/0122 →
SECURITY INTEREST Recorded Nov 10, 2022
From: XEROX CORPORATION
To: CITIBANK, N.A., AS AGENT
Reel/Frame 062740/0214 →
CORRECTIVE ASSIGNMENT TO ADD OMITTED ASSIGNORS PREVIOUSLY RECORDED AT REEL 027110 FRAME 0632. THE ASSIGNORS HEREBY CONFIRM THE ASSIGNMENT OF THE ENTIRE INTEREST. Recorded Nov 9, 2011
From: WU, JIN; ZHANG, LANHUI; MA, LIN
To: XEROX CORPORATION
Reel/Frame 027264/0685 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2011
From: WU, JIN
To: XEROX CORPORATION
Reel/Frame 027110/0632 →