IP Library Granted Patent US 7,652,115
Granted Patent B2
US 7,652,115 · App. 10/657,644 · Granted Jan 26, 2010

Fluorinated polyether isocyanate derived silane compositions

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Quick Facts
Patent No.
US 7,652,115
App. No.
10/657,644
Granted
Jan 26, 2010
Kind
B2
Abstract

Described are compositions containing fluorinated polyether isocyanate derived silane compounds for treating substrates such as hard surfaces, e.g. ceramic and/or glass, to render them oil and water repellent, and stain resistant, articles having coatings comprising such compounds, and methods for applying such coatings.

Claims (40)

1. A composition comprising a mixture of:

(a) a perfluoropolyether urethane or urea silane or a mixture thereof comprising the reaction product of:

(i) a fluorinated polyether compound of the formula

(T′) y -R f -T  (I)

wherein R f is a monovalent or divalent polyfluoropolyether group; T and T′ each independently represent —CO 2 R 3 , where R 3 is hydroxyalkyl, or —C(O)N(R 1 )(R 2 ), where R 1 is hydroxyalkyl, dihydroxypropyl, or polyalkylenepolyamine and R 2 is hydrogen or R 1 ; and y is 0 or 1; and

(ii) a silane compound of the formula

T″-Q″-SiY 3-x R′ x   (II)

wherein T″ is —NCO; Q″ is —(C n H 2n )—, where n is 2 to 6 ; R′ is an alkyl group of 1-4 carbon atoms; Y is a C 1 -C 4 alkoxy group, a halide, an acyloxy group, or a polyoxyalkylene group; and x is 0 or 1; and

(b) an organic solvent.

2. The composition according to claim 1 wherein T and T′ each independently represent —C(O)N(R 1 )(R 2 ), where R 1 is hydroxyalkyl, dihydroxypropyl, or polyalkylenepolyamine, and R 2 is hydrogen.

3. The composition according to claim 1 wherein R 1 is hydroxyalkyl, dihydroxypropyl, or polyalkylenepolyamine, and R 2 is hydrogen.

4. A composition according to claim 1 , further comprising a fluorosurfactant.

5. A composition according to claim 4 , wherein the fluorosurfactant has the structure

wherein the molar ratio of a:b:c is about 30:about 1 :about 32 and wherein the molecular weight of the fluorosurfactant is about 1,000 to about 4,000 grams per mole, or wherein the fluorosurfactant has the structure

wherein the molar ratio of a′:b′:c′ is about 3:about 3:about 1 and wherein the molecular weight of the fluorosurfactant is about 2,000 to about 40,000 grams per mole, or mixtures thereof.

6. A composition according to claim 1 , wherein said organic solvent is an aliphatic alcohol, a ketone, an ester, an ether, an amide, or a mixture thereof.

7. A composition according to claim 1 , wherein said organic solvent comprises a fluorinated organic solvent.

8. A composition according to claim 1 , wherein R f in Formula (I) is of the formula:

—((R f 3 ) q′ —R f 2 —O) z′ —R f 1 —(O—R f 2 —(R f 3 ) q ) z —  (III)

wherein R f 1 is a perfluorinated alkyl or a perfluorinated alkylene group, R f 2 is a perfluorinated polyalkyleneoxy group consisting of perfluorinated alkyleneoxy groups having 1, 2, 3 or 4 carbon atoms or a mixture of such perfluorinated alkyleneoxy groups; R f 3 is a perfluorinated alkylene group or a substituted perfluorinated alkyl group; q and q′ are independently chosen from 0 or 1; z is from 4 to 30, and z′ is 0 to 30.

9. A composition according to claim 8 , wherein R f 2 comprises repeating units selected from the group consisting of —(C n F 2n O)—,—(CF(Z)O)—, —(C n F 2n CF(Z)O)—, and —(CF 2 CF(Z)O)—, and combinations thereof, wherein n is at least 1 and wherein Z is a fluorine atom, a perfluoroalkyl group, a substituted perfluoroalkyl group, an oxygen-substituted perfluoroalkyl group, a perfluoroalkoxy group, or an oxygen-substituted perfluoroalkoxy group.

10. A composition according to claim 8 , wherein R f 3 comprises repeating units selected from the group consisting of —(C n F 2n )— and —(CF(Z))—, and combinations thereof, wherein n is at least 1 and wherein Z is a fluorine atom, a perfluoroalkyl group, a substituted perfluoroalkyl group, an oxygen-substituted perfluoroalkyl group, a perfluoroalkoxy group, or an oxygen-substituted perfluoroalkoxy group.

11. A composition according to claim 1 , wherein R f is —CF 2 O(CF 2 O) m (C 2 F 4 O) p CF 2 —, —CF 2 O(C 2 F 4 O) p CF 2 —, CF(CF 3 )(OCF 2 (CF 3 )CF) p O(CF 2 ) m O(CF(CF 3 )CF 2 O) p CF(CF 3 )—, CF 3 CF 2 CF 2 O(CF(CF 3 )CF 2 O) p CF(CF 3 )—, or combinations thereof, where an average value for m and p is 0 to 50 and m and p are not independently 0.

12. A composition according to claim 1 wherein R f is CF 3 CF 2 O(CF 2 O) m —(C 2 F 4 O) p CF 2 —, CF(CF 3 )(OCF 2 (CF 3 )CF) p O(CF 2 ) m O(CF(CF 3 )CF 2 O) p CF(CF 3 )—, CF 3 CF 2 O(C 2 F 4 O) p CF 2 —, CF 3 CF(CF 3 )O—(CF(CF 3 )CF 2 O) p CF(CF 3 )—, or combinations thereof, where an average value for m and p is 0 to 50 and m and p are not independently 0.

13. A method for treating a substrate comprising the step of applying a composition according to claim 1 to said substrate.

14. The method according to claim 13 , wherein said method further comprises curing the applied composition at elevated temperature.

15. The method according to claim 13 , wherein said substrate is a ceramic or a glass substrate.

16. The method according to claim 13 , wherein the substrate is an antireflective surface, wherein said coating composition forms an antisoiling coating thereon.

17. A composition comprising:

(a) a perfluoropolyether urethane or urea silane or a mixture thereof comprising the reaction product of:

(i) a fluorinated polyether compound of the formula

(T′) y -R f -T  (I)

wherein R f is a monovalent or divalent polyfluoropolyether group; T and T′ each independently represent —CO 2 R 3 , where R 3 is hydroxyalkyl, or —C(O)N(R 1 )(R 2 ), where R 1 is hydroxyalkyl, dihydroxypropyl, or polyalkylenepolyamine and R 2 is hydrogen or R 1 ; and y is 0 or 1; and

(ii) a silane compound of the formula

T″-Q″-SiY 3-x R′ x   (II)

wherein T″ is —NCO; Q″is —(C n H 2n )—, where n is 2 to 6; R′ is an alkyl group of 1-4 carbon atoms; Y is a C 1 -C 4 alkoxy group, a halide, an acyloxy group, or a polyoxyalkylene group; and x is 0 or 1.

18. The composition according to claim 17 wherein T and T′ each independently represent —C(O)N(R 1 )(R 2 ), where R 1 is hydroxyalkyl, dihydroxypropyl, or polyalkylenepolyamine, and R 2 is hydrogen.

19. The composition according to claim 17 wherein R 1 is hydroxyalkyl, dihydroxypropyl, or polyalkylenepolyamine, and R 2 is hydrogen.

20. An article having a surface, at least a portion of said surface having a coating thereon, said coating comprising a composition according to claim 17 .

21. The article of claim 20 wherein said article is a ceramic or glass substrate.

Assignments (4)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL RECORDED AT R/F 053586/0715 Recorded Dec 12, 2022
From: MIDCAP FINANCIAL TRUST, AS ADMINISTRATIVE AGENT
To: KINDEVA DRUG DELIVERY L.P.
Reel/Frame 062115/0707 →
SECURITY INTEREST Recorded Aug 24, 2020
From: KINDEVA DRUG DELIVERY L.P.
To: MIDCAP FINANCIAL TRUST, AS ADMINISTRATIVE AGENT
Reel/Frame 053586/0715 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2020
From: 3M COMPANY; 3M INNOVATIVE PROPERTIES COMPANY
To: KINDEVA DRUG DELIVERY L.P.
Reel/Frame 052818/0234 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2004
From: DAMS, RUDOLF J.; MARTIN, STEVEN J.; FLYNN, RICHARD M.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 014894/0352 →