IP Library Granted Patent US 8,338,531
Granted Patent B2
US 8,338,531 · App. 13/006,917 · Granted Dec 25, 2012

Epoxy silane oligomer and coating composition containing same

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Quick Facts
Patent No.
US 8,338,531
App. No.
13/006,917
Granted
Dec 25, 2012
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 (18)

1. A process for producing a waterborne coating composition comprising an epoxysilane oligomer, a particulate metal, a surfactant and water, said method comprising: reacting glycidoxy silane having 2 alkoxy groups with water in the presence of a catalyst selected from the group consisting of an ion exchange resin, an alkylammonium salt, and a reaction product of a quaternary ammonium organofunctional silane and a ceramic, silica gel, precipitated silica, alumina or aluminosilicate support, wherein said water is continuously fed during the reaction and the molar ratio of water to silane monomer is from 0.1 to 1.5.

2. The process of claim 1 , wherein the molar ratio of water to silane monomer is from 0.4 to 1.0.

3. The process of claim 1 , wherein the molar ratio of water to silane monomer is from 0.1 to 0.5.

4. The process of claim 1 wherein the catalyst is at least one member selected from the group consisting of, hexadecyltrimethylammonium chloride, tetra-n-butylammonium chloride, benzyl trimethylammonium chloride, hexadecyltrimethylammonium bromide, tetra-n-butylammonium bromide, benzyl trimethylammonium bromide, hexadecyltrimethylammonium hydroxide, tetra-n-butylammonium hydroxide and benzyl trimethylammonium hydroxide.

5. The process of claim 1 wherein the glycidoxy silane is selected from the group consisting of gamma-glycidoxypropyl methyldimethoxysilane and gamma-glycidoxypropyl methyldiethoxysilane.

6. The process of claim 1 which further comprises continuously removing by-product alcohol produced during the reaction.

7. A waterborne coating composition, comprising:

a particulate metal;

a surfactant;

epoxy silane oligomer made by the process of reacting glycidoxy silane having 2 alkoxy group with water in the presence of a catalyst selected from the group consisting of an ion exchange resin, an alkylammonium salt, and a reaction product of a quaternary ammonium organofunctional silane and a ceramic, silica gel, precipitated silica, alumina or aluminosilicate support, wherein said water is continuously fed during the reaction and the molar ratio of water to silane monomer is from 0.1 to 1.5;

water; and,

one or more optional ingredients selected from the group consisting of pH adjusting agent, cosolvent, epoxy silane monomer, surfactant, binder, and pigment paste dispersion.

8. The waterborne coating composition of claim 7 wherein the particulate metal is present in an amount of from 0.1 to 80 weight percent, the surfactant is present in an amount of from 0.05 to 10 weight percent, the epoxy silane oligomer is present in an amount of from 0.1 to 30 weight percent, and water is present in an amount of from 5 to 99 weight percent.

9. The waterborne coating composition of claim 7 wherein the particulate metal is selected from the group consisting of finely divided aluminum, manganese, cadmium, nickel, stainless steel, tin, ferroalloys, magnesium and zinc.

10. The waterborne composition of claim 7 including a pH adjusting agent comprising at least one member selected from the group consisting of boric acid, orthophosphoric acid, acetic acid, and citric acid in an amount sufficient to provide a pH of from 4 to 6.

11. The waterborne composition of claim 7 including a co-solvent present in an amount of from 0.1 to about 60 weight percent based upon the total weight of the composition, wherein said 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.

12. The waterborne composition of claim 7 including an epoxy silane monomer present in an amount of up to 10 weight percent based on the total weight of the composition, wherein said epoxy silane monomer is selected from the group consisting of gamma-glycidoxypropyl trimethoxy silane, gamma-glycidoxypropyl triethoxy silane, gamma-glycidoxypropyl methyldimethoxy silane and gamma-glycidoxypropyl methyldiethoxy silane.

13. An adhesive, sealant or coating composition which comprises the waterborne composition of claim 7 .

Assignments (23)
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 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded May 4, 2023
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063548/0383 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
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 →
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
Reel/Frame 049388/0220 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →
SECURITY AGREEMENT Recorded Mar 28, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 027944/0386 →