Process for producing anti-fog coating

• US 8,231,971 B2
• Filed: 11/16/2006
• Issued: 07/31/2012
• Est. Priority Date: 11/16/2005
• Status: Expired due to Fees

• Current Assignee: Universite Laval
• Original Assignee: Universite Laval
• Inventors: Laroche, Gaétan, Mantovani, Diego, Chevalier, Pascale
• Primary Examiner(s): Shosho, Callie
• Assistant Examiner(s): FREEMAN, JOHN D
• Application Number:
  US12/093,916
• Publication Number:
  US 20090246513A1
• Time in Patent Office: 2,084 Days
• Field of Search: 428/420, 428/412, 428/507, 428/520, 106/13, 156/307.1, 156/307.7, 523/169
• US Class Current: 428/420
• CPC Class Codes: C03C 17/3405 with at least two coatings of organic materials C03C17/36, C03C17/42 take precedence
• CPC Class Codes: C03C 2218/111 by dipping, immersion
• CPC Class Codes: C03C 2218/116 by spin-coating, centrifugation
• CPC Class Codes: C03C 2218/32 After-treatment
• CPC Class Codes: C03C 23/006 by plasma or corona discharge
• CPC Class Codes: C08J 2333/12 Homopolymers or copolymers of methyl methacrylate
• CPC Class Codes: C08J 2369/00 Characterised by the use of polycarbonates; Derivatives of polycarbonates
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C08J 7/054 Forming anti-misting or drip-proofing coatings
• CPC Class Codes: C08J 7/123 Treatment by wave energy or particle radiation C08J7/18 takes precedence
• CPC Class Codes: C09D 101/12 Cellulose acetate
• CPC Class Codes: C09D 101/28 Alkyl ethers
• CPC Class Codes: C09D 101/284 with hydroxylated hydrocarbon radicals
• CPC Class Codes: C09D 105/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09D 135/00 Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09J 135/00 Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
• CPC Class Codes: Y10T 428/265 1 mil or less
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31536 Including interfacial reaction product of adjacent layers
• CPC Class Codes: Y10T 428/31645 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31794 : Of cross-linked polyester
• CPC Class Codes: Y10T 428/31797 : Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/3188 : Next to cellulosic
• CPC Class Codes: Y10T 428/31928 : Ester, halide or nitrile of addition polymer

Abstract

The invention relates to an anti-fog coating for a surface of a substrate comprising: a first polymer layer resulting from covalently bonding a polyanhydride polymer to said surface; and a second polymer layer resulting from covalently bonding a polymer selected from the group consisting of polyvinyl alcohol, partially hydrolyzed polyester, polyether and cellulose derivative; said surface having nucleophilic groups. A substrate having an anti-fog coating, as well as a process for preparing said anti-fog coating to the surface of a substrate is also provided.

Claims

1. A process for preparing an anti-fog coating on a surface of a substrate comprising:

a) providing nucleophilic groups at the surface of said substrate, wherein said nucleophilic groups are selected from hydroxyl groups, thiol groups, amino groups, aminosilanes and mixtures thereof;

b) adding a first polymer layer by covalently bonding a polyanhydride polymer to said nucleophilic groups; and

c) adding a second polymer layer by covalently bonding a polymer selected from the group consisting of polyvinyl alcohol, partially hydrolyzed polyvinyl ester and polyether to said first polymer layer wherein the polyanhydride is selected from poly(ethylene-alt-maleic anhydride), poly(maleic anhydride-alt-1-octadecene), poly(isobutylene-alt-maleic anhydride), poly(styrene-alt-maleic anhydride), poly(methyl vinyl ether-alt-maleic anhydride) and poly[(isobutylene-alt-maleic acid, ammonium salt)-co-(isobutylene-alt-maleic anhydride)].

2. The process of claim 1, wherein said steps b) and c) are repeated a plurality of times to provide a plurality of said first and second polymer layers.

3. The process of claim 2, wherein said coating has a thickness of up to about 90 nm.

4. The process as defined in claim 1, wherein said polyanhydride polymer is poly(ethylene-alt maleic anhydride).

5. The process as defined in claim 1, wherein the polyanhydride polymer is poly(maleic anhydride-alt-1-octadecene).

6. The process as defined in claim 1, wherein the polyanhydride polymer is poly(methyl vinyl ether-alt-maleic anhydride).

7. The process as defined in claim 1, wherein said nucleophilic groups are selected from hydroxyl groups, thiol groups, amino groups and mixtures thereof.

8. The process as defined in claim 1, wherein said step a) comprises treating said surface with a gas plasma selected from NH₃, mixture of N₂/H₂, alkylamine and mixtures thereof.

9. The process as defined in claim 8, wherein said step a) comprises treating said surface with a gas plasma of a mixture of N₂/H₂.

10. The process as defined in claim 1, wherein said step a) comprises a chemical functionalization.

11. The process as defined in claim 10, wherein said chemical functionalization comprises aminosilylation.

12. The process as defined in claim 1, wherein there is at least 0.5% of said nucleophilic groups at the surface of the substrate.

13. The process as defined in claim 1, wherein step (b) further comprises the step of cross-linking said first polymer layer.

14. The process as defined in claim 1, wherein step (c) further comprises cross-linking said first and second polymer layers.

15. The process as defined in claim 1, wherein the second polymer is bonded by spin coating.

16. The process as defined in claim 1, wherein the second polymer is bonded by dip coating.

17. A process for preparing an anti-fog coating to a surface of a substrate as defined in claim 1, comprising:

a) providing nucleophilic groups at the surface of said substrate, wherein said nucleophilic groups are selected from hydroxyl groups, thiol groups, amino groups, aminosilanes and mixtures thereof;

b) adding a first polymer layer by covalently bonding a polyanhydride polymer to said nucleophilic groups;

b1) optionally cross-linking said first polymer layer;

c) adding a second polymer layer by covalently bonding a polymer selected from the group consisting of polyvinyl alcohol, partially hydrolyzed polyvinyl ester and polyether to said first polymer layer; and

1) when said first polymer layer has been cross-linked in step b1) above, then the process further comprises the step of cross-linking said second polymer layer;

or

2) when said first polymer layer has not been cross-linked in step b1) above, then the process comprises the step of cross-linking said first and second polymer layers.

18. A substrate having an anti-fog coating thereon,

wherein said substrate has a surface comprising nucleophilic groups selected from hydroxyl groups, thiol groups, amino groups, aminosilanes and mixtures thereof;

and

said coating comprises;

a first polymer layer resulting from covalently bonding a polyanhydride polymer to said nucleophilic groups, and

a second polymer layer resulting from covalently bonding a polymer selected from the group consisting of polyvinyl alcohol, partially hydrolyzed polyvinyl ester and polyether to said first polymer layer wherein the polyanhydride is selected from poly(ethylene-alt-maleic anhydride), poly(maleic anhydride-alt-1-octadecene), poly(isobutylene-alt-maleic anhydride), poly(styrene-alt-maleic anhydride), poly(methyl vinyl ether-alt-maleic anhydride) and poly[(isobutylene-alt-maleic acid, ammonium salt)-co-(isobutylene-alt-maleic anhydride)].

19. The substrate as defined in claim 18, wherein said coating comprises a plurality of said first and said second polymer layers.

20. The substrate as defined in claim 18, wherein said coating has a thickness of up to about 90 nm.

21. The substrate as defined in claim 18, wherein the polyanhydride polymer is poly(ethylene-alt maleic anhydride).

22. The substrate as defined in claim 18, wherein the polyanhydride polymer is poly(maleic anhydride-alt-1-octadecene).

23. The substrate as defined in claim 18, wherein the polyanhydride polymer is poly(methyl vinyl ether-alt-maleic anhydride).

24. The substrate as defined in claim 18, wherein said nucleophilic groups are selected from hydroxyl groups, thiol groups, amino groups and mixtures thereof.

25. The substrate as defined in claim 18, wherein said substrate is a glass or a polymeric material.

26. The substrate as defined in claim 25, wherein the polymeric substrate is polycarbonate or polymethylmethacrylate.