IP Library Granted Patent US 7,595,372
Granted Patent B2
US 7,595,372 · App. 11/297,714 · Granted Sep 29, 2009

Epoxy silane oligomer and coating composition containing same

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Quick Facts
Patent No.
US 7,595,372
App. No.
11/297,714
Granted
Sep 29, 2009
Kind
B2
Abstract

A process for producing an epoxy silane oligomer including a reaction glycidoxy silane and/or cycloaliphatic epoxy silane having 2 or 3 alkoxy groups and, optionally, a copolymerizable silane other than glycidoxy and cycloaliphatic epoxy silane, with less than 1.5 equivalents of water in the presence of a catalyst, wherein said water is continuously fed during the reaction.

Claims (26)

1. A waterborne composition which comprises:

i) a water soluble epoxy silane oligomer composition containing from 7.46 to 23.5 weight percent residual monomer, wherein the epoxy silane oligomer is produced by the reaction of glycidoxy silane having 3 alkoxy groups with water, wherein the molar ratio of water to silane monomer is from 0.1 to 1.5, in the presence of a catalyst, wherein said water is continuously fed during the reaction and the by-product alcohol is continuously removed during the reaction;

ii) at least one particulate metal selected from the group consisting of aluminum, manganese, cadmium, nickel, tin, magnesium, zinc, alloys thereof and ferroalloys thereof; and,

iii) one or more optional ingredients selected from the group consisting of a surfactant, pH adjusting agent, co-solvent, monomeric silane, binder, crosslinker and pigment paste dispersion.

2. The waterborne composition of claim 1 wherein the epoxy silane oligomer composition is pre-solubilized in an aqueous solution.

3. The composition of claim 1 wherein optional pH adjusting agent is at least one member selected from the group consisting of boric acid, orthophosporic acid, acetic acid, ascorbic acid and citric acid; optional co-solvent is at least one member of the group consisting of dipropylene glycol methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, ethylene glycol monophenyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, butyl carbitol, dipropylene glycol dimethyl ether, butyl glycol, butyldiglycol, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, n-propyl acetate, n-butyl acetate, isobutyl acetate, methoxypropylacetate, butyl cellosolve actetate, butylcarbitol acetate, propylene glycol n-butyl ether acetate, t-butyl acetate, n-butanol, n-propanol, isopropanol and ethanol.

4. The composition of claim 1 wherein the surfactant is at least one member selected from the group consisting of alkyl-phenol-ethoxylate surfactant, cationic surfactant, anionic surfactant, non-ionic surfactant, a polyether siloxane-based surfactant and any combination thereof.

5. The composition of claim 1 wherein the surfactant has a hydrophilic-lipophilic balance value of from about 5 to about 15.

6. The composition of claim 1 wherein the binder is selected from the group consisting organic or inorganic binders.

7. The composition of claim 6 wherein the inorganic binder is selected from the group consisting of silicates, ethyl silicates, silica nano particles solutions and silicone resins.

8. The composition of claim 6 wherein the organic binder is selected from the group consisting of non-ionic stabilized resins, anionic stabilized emulsions and cationic stabilized emulsions.

9. The composition of claim 8 wherein the organic binder is selected from the group consisting of vinylic resins, polyvinyl chlorides, vinyl chloride copolymers, vinylacetate copolymers, acrylics copolymers, styrene butadiene copolymers, acrylate copolymer, polyacrylate, styrene acrylate copolymers, phenolic resins, melamine resins, epoxy resins, polyurethane resins, alkyd resins, polyvinyl butyral resins, polyamides, polyamidoamines resins, polyvinyl ethers, polybutadienes, polyester resins, organosilicone resins, organopolysiloxane resins, nitrocellulosic resins, carboxymethyl cellulose, cellulose esters of organic acids, cellulose ethers, modified natural rubbers, natural gums, a solution of said polymers and copolymers, and any combination thereof.

10. The composition of claim 1 wherein the crosslinker is selected from the group consisting of isocyanates, epoxy curing agents, amino agents, aminoamido agents, epoxy amino adducts, carbodiimides, melamines anhydrides, polycarboxylic anhydrides, carboxylic acid resins, aziridines, titanates, organofunctional titanates and organofunctional silanes.

11. The composition of claim 10 wherein the organofunctional silane is selected from the group consisting of epoxy silanes, aminosilanes, isocyanatosilanes, methacryl silanes and vinylsilanes.

12. The composition of claim 1 wherein the pigment paste dispersion is selected from the group consisting of organic pigment dispersions and inorganic pigment dispersions.

13. The composition of claim 1 wherein the epoxy silane oligomer composition is present in the range of about 0.05 to about 40 weight percent of the composition.

14. The cured composition of claim 1 .

15. An adhesive, sealant or coating composition which comprises the waterborne composition of claim 1 .

16. The composition of claim 1 wherein the particulate metal is selected from the group consisting of zinc dust, zinc flake, aluminum dust, aluminum flake, zinc aluminum alloy dust, zinc aluminum alloy flakes and any combination thereof.

17. The composition of claim 1 wherein the particulate metal is in a powder or paste dispersion form.

18. A waterborne composition which comprises:

i) an epoxy silane oligomer, composition containing from 15 to 23.5 weight percent residual monomer, wherein the epoxy silane oligomer is produced by the reaction of glycidoxy silane and/or cycloaliphatic epoxy silane having 3 alkoxy groups with water wherein the ratio of water to silane monomer is from 0.1 to 1.5 in the presence of a catalyst, wherein said water is continuously fed during the reaction and wherein the epoxy silane oligomer composition is pre- solubilized in an aqueous solution; and,

ii) one or more optional ingredients selected from the group consisting of a surfactant, pH adjusting agent, co-solvent, monomeric silane, binder, crosslinker and pigment paste dispersion, and,

iii) at least one particulate metal selected from the group consisting of zinc chromate, zinc potassium chromate, zinc phosphates, alumino triphosphates, calcium magnesium phosphates, barium phosphates, aluminum zinc phosphates, molybdates, wolframates, zirconates, vanadates, zinc salts of 5-nitrophthalic acid and iron phosphide.

19. A coating composition which comprises the composition of claim 18 .

20. The cured product of claim 19 .

Assignments (27)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
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From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
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SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
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FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
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TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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Reel/Frame 049194/0085 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
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NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
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