IP Library Granted Patent US 7,879,456
Granted Patent B2
US 7,879,456 · App. 12/169,324 · Granted Feb 1, 2011

Carrier applied coating layers

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Quick Facts
Patent No.
US 7,879,456
App. No.
12/169,324
Granted
Feb 1, 2011
Kind
B2
Abstract

Methods for bonding adherent phosphorous-containing coating layers to oxide surfaces on substrates wherein the substrates with oxide surfaces are selected from: (a) oxidized iron, titanium, silicon, tin and vanadium; (b) indium tin oxide; and (c) substrates with oxide layers deposited thereon, wherein the substrates on which oxide layers are deposited are selected from ceramics, semiconductors, metals, plastics and glass, and the method contacts the oxide surface with a carrier conveying an organo-phosphonic acid coating composition and heats the oxide surface and carrier at a sufficient temperature while maintaining contact for a sufficient time to bond a layer of the organophosphonic acid to the oxide surface. Coated articles prepared by the inventive method are also disclosed.

Claims (37)

1. A method of bonding an adherent phosphorous-containing coating layer to an oxide surface on a substrate, wherein said substrate with an oxide surface is selected from the group consisting of:

(a) oxidized iron, titanium, silicon, tin and vanadium;

(b) indium tin oxide; and

(c) substrates with oxide layers deposited thereon, wherein said substrates on which said oxide layers are deposited are selected from the group consisting of ceramics, semiconductors, metals, plastics and glass,

said method comprising: (i) adsorbing or absorbing onto a hydrophilic carrier a solution comprising a coating composition comprising an organophosphonic acid compound, (ii) contacting said oxide surface with said carrier conveying said coating composition, and (iii) heating said oxide surface and carrier at a sufficient temperature while maintaining contact for a sufficient time to bond a layer of said organophosphonic acid compound to said oxide surface, wherein said adherent phosphorus-containing coating layer comprises said organophosphonic acid compound in an amount up to about 10 times greater than the amount in a coated article comprising the same substrate and oxide surface that is treated directly with said solution comprising said coating composition.

2. The method of claim 1 , wherein said oxidized iron comprises oxidized steel.

3. The method of claim 2 wherein said oxidized steel is oxidized stainless steel.

4. The method of claim 1 wherein said oxide surface is an oxide layer deposited on a substrate.

5. The method of claim 4 wherein said substrate with an oxide surface layer comprises an oxide layer deposited on a substrate selected from the group consisting of gallium arsenide, gallium nitride, silicon carbide, silicon nitride, germanium and semiconducting compounds comprising germanium.

6. The method of claim 4 wherein said substrate with an oxide surface layer comprises an oxide insulator deposited on a substrate or an oxide conductor deposited on a substrate.

7. The method of claim 1 wherein said organophosphonic acid compound is a diphosphonic acid.

8. The method of claim 7 , wherein said organophosphonic acid compound is 1,12-diphosphonododecane diphosphonic acid.

9. The method of claim 1 , wherein said substrate is selected from the group consisting of plastics, glass, ceramic, semi-conductors, and metals.

10. The method of claim 1 , wherein the organo group of the organophosphonic acid compound is selected independently for each occurrence from the group consisting of: (a) optionally substituted linear and branched, saturated and unsaturated hydrocarbon moieties having from about 2 to about 40 carbon atoms; (b) optionally substituted oligoarene and polyarene moieties; and (c) substituted and unsubstituted tetracyanoquinodimethane and tetrathiofulvalene moieties.

11. The method of claim 1 , wherein the organo group of the organophosphonic acid compound comprises functional groups selected independently for each occurrence from the group consisting of hydroxyl, amino, carboxylic acid, phosphonic acid, thiol, maleimido and succinimidoyl functional groups.

12. The method of claim 1 wherein the organo group of the organophosphonic acid compound is a linear alkyl group having at least one carbon chain of from about 2 to about 20 carbon atoms in length and an omega-substituent selected from the group consisting of hydroxyl, amino, carboxylic acid, phosphonic acid, thiol, maleimido and succinimidoyl functional groups.

13. The method of claim 1 , wherein the organo group of the organophosphonic acid compound is selected independently for each occurrence from the group consisting of substituted and unsubstituted thiophene moieties, substituted and unsubstituted polythiophene moieties, substituted and unsubstituted oligomeric and polymeric arene moieties, organic electron donor moieties, organic electron acceptor moieties, tetracyanoquinodimethane moieties and tetrathiofulvalene moieties.

14. The method of claim 1 , wherein the organo group of the organophosphonic acid compound comprises electronic conductor moieties.

15. The method of claim 14 , wherein said electronic conductor moieties are selected from the group consisting of tetracyanoquinodimethane and tetrafluorotetracyanoquinodimethane.

16. The method of claim 1 , wherein said coating composition comprises at least one organophosphonic acid compound having an omega-carbon substituent selected from the group consisting of carboxylic acid, phosphonic acid, hydroxyl, amino, and thiol functional groups, and the method further comprises: (a) contacting at least a portion of said coating layer with a reagent capable of a bond-forming reaction with said omega-carbon substituents; and (b) forming a bond between at least a portion of said contacting reagent and at least a portion of said omega-carbon substituents.

17. The method of claim 16 , wherein said contacting step (a) is achieved by applying a printing medium containing said reagent to said coating layer.

18. The method of claim 17 wherein said printing medium is applied by a method selected from ink-jet printing, stamping, screen printing and lithography.

19. The method of claim 17 wherein said printing medium is applied in a pattern.

20. The method of claim 16 , wherein at least a portion of said omega-functional groups are selected from the group consisting of carboxylic acid and hydroxyl functional groups and said reagent is a protein coupling reagent.

21. A coated article comprising a substrate with an oxide surface and an adherent phosphorus-containing coating layer bonded to said oxide surface, wherein said substrate with an oxide surface is selected from the group consisting of:

(a) oxidized iron, titanium, silicon, tin and vanadium;

(b) indium tin oxide; and

(c) substrates with oxide layers deposited thereon, wherein said substrates on which oxide layers are deposited are selected from the group consisting of ceramics, semiconductors, metals, plastics and glass,

and said adherent phosphorus-containing coating layer bonded thereto is produced by a method comprising (i) adsorbing or absorbing onto a hydrophilic carrier a solution comprising a coating composition comprising an organophosphonic acid compound, (ii) contacting said oxide surface of said article with said carrier conveying said coating composition, and (iii) heating said oxide surface and said carrier at a sufficient temperature while maintaining contact for a sufficient time to bond said organophosphonic acid compound to said oxide surface, wherein said adherent phosphorus-containing coating layer comprises said organophosphonic acid compound in an amount up to about 10 times greater than the amount in a coated article comprising the same substrate and oxide surface that is treated directly with said solution comprising said coating composition.

22. The coated article of claim 21 , wherein said oxidized iron comprises oxidized steel.

23. The coated article of claim 22 wherein said oxidized steel is oxidized stainless steel.

24. The coated article of claim 21 , wherein said oxide surface is an oxide layer deposited on a substrate.

25. The coated article of claim 24 , wherein said substrate with an oxide surface layer comprises an oxide layer deposited on a substrate selected from the group consisting of gallium arsenide, gallium nitride, silicon carbide, silicon nitride, germanium and semi-conducting compounds comprising germanium.

26. The coated article of claim 24 , wherein said substrate with an oxide surface layer comprises an oxide insulator deposited on a substrate or an oxide conductor deposited on a substrate.

27. The coated article of claim 21 , wherein the organo group of the organophosphonic acid compound comprises functional groups selected independently for each occurrence from the group consisting of hydroxyl, amino, carboxylic acid, phosphonic acid, thiol, maleimido and succinimidoyl functional groups.

28. The coated article of claim 21 , wherein the organo group of the organophosphonic acid compound comprises electronic conductor moieties.

29. The coated article of claim 28 wherein said electronic conductor moieties are selected from the group consisting of tetracyanoquinodimethane and tetrafluorotetracyanoquinodimethane.

Assignments (2)
CONFIRMATORY LICENSE Recorded Apr 12, 2011
From: PRINCETON UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 026108/0638 →
CONFIRMATORY LICENSE Recorded Jun 17, 2010
From: SCHWARTZ, JEFFREY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 024551/0199 →
Continuity (14)
Continuation 1087629400 · Jun 23, 2004
Continuation In Part 1017974300 · Jun 24, 2002
Continuation In Part 0966808000 · Sep 22, 2000
Continuation In Part 0879483300 · Feb 4, 1997
Continuation In Part 1040555700 · Apr 1, 2003
Continuation In Part 1017974300 · Jun 24, 2002
Provisional Application 6048067000 · Jun 23, 2003
Provisional Application 6030014400 · Jun 22, 2001
Provisional Application 6015539800 · Sep 22, 1999
Provisional Application 6002894900 · Oct 17, 1996
Provisional Application 6003504000 · Jan 13, 1997
Provisional Application 6036923600 · Apr 1, 2002
Provisional Application 6036923700 · Apr 1, 2002
Related Publication 20090004481A1 · Jan 1, 2009