IP Library Granted Patent US 7,893,183
Granted Patent B2
US 7,893,183 · App. 11/100,840 · Granted Feb 22, 2011

Epoxy silane oligomer and coating composition containing same

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Quick Facts
Patent No.
US 7,893,183
App. No.
11/100,840
Granted
Feb 22, 2011
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 (13)

1. An epoxy silane oligomer made by the process comprising reacting in the presence of a catalyst (i) glycidoxy silane having 3 alkoxy groups and (ii) a polyalkyleneoxide functional silane with water that is continuously fed during the reaction and is in a molar ratio of 0.4 to 1.0 water to silane monomers (i) and (ii),

wherein the epoxy silane oligomer has a viscosity of 7 to 86 mPa·s and a residual monomer content less than 23.5 weight percent based upon the total weight of the residual monomer and epoxy silane oligomer.

2. The epoxy silane oligomer of claim 1 , wherein the glycidoxy silane is at least one member selected from the group consisting of gamma-glycidoxypropyl trimethoxysilane and gamma-glycidoxypropyl triethoxysilane.

3. The epoxy silane oligomer of claim 1 wherein the reaction is carried out in the presence of an alcohol-free solvent.

4. The epoxy silane oligomer of claim 3 wherein the alcohol-free solvent is at least one member selected from the group consisting of acetone, toluene, aliphatic hydrocarbon, paraffin, aromatic hydrocarbon, ketone and ester.

5. The epoxy silane oligomer of claim 1 , wherein the catalyst is at least one member selected from the group consisting of ion exchange resin, titanate, Lewis acid, zirconate, alkylammonium salt, quaternary ammonium-functional silane reacted with at least one of ceramic, silica gel, precipitated or fumed silica, alumina and aluminosilicate.

6. The epoxy silane oligomer of claim 5 , 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.

7. An epoxy silane oligomer made by the process comprising reacting in the presence of a catalyst (i) a glycidoxy silane having 2 alkoxy groups and (ii) a polyalkyleneoxide functional silane, with water that is continuously fed during the reaction and in a molar ratio of 0.4 to 1.0 water to silane monomers (i) and (ii), wherein the epoxy silane oligomer has a viscosity of 7 to 86 mPa·s and a residual monomer content less than 23.5 weight percent based upon the total weight of the residual monomer and epoxy silane oligomer.

8. The epoxy silane oligomer of claim 7 , wherein the glycidoxy silane is at least one member selected from the group consisting of gamma-glycidoxypropyl methyl dimethoxysilane and gamma-glycidoxypropylmethyl diethoxysilane.

9. The epoxy silane oligomer of claim 7 wherein the reaction is carried out in the presence of an alcohol-free solvent.

10. The epoxy silane oligomer of claim 9 wherein the alcohol-free solvent is at least one member selected from the group consisting of acetone, toluene, aliphatic hydrocarbon, paraffin, aromatic hydrocarbon, ketone and ester.

11. The epoxy silane oligomer of claim 7 , wherein the catalyst is at least one member selected from the group consisting of ion exchange resin, titanate, Lewis acid, zirconate, alkylammonium salt, quaternary ammonium-functional silane reacted with at least one of ceramic, silica gel, precipitated or fumed silica, alumina and aluminosilicate.

12. The epoxy silane oligomer of claim 11 , 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.

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.
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FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
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RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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 Dec 24, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054883/0855 →
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
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SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
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FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
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To: BNP PARIBAS, 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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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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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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NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
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TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
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SECURITY INTEREST Recorded Oct 27, 2014
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From: MOMENTIVE PERFORMANCE MATERIALS, INC.; JUNIPER BOND HOLDINGS I LLC; JUNIPER BOND HOLDINGS II LLC; JUNIPER BOND HOLDINGS III LLC; JUNIPER BOND HOLDINGS IV LLC; MOMENTIVE PERFORMANCE MATERIALS CHINA SPV INC.; MOMENTIVE PERFORMANCE MATERIALS QUARTZ, INC.; MOMENTIVE PERFORMANCE MATERIALS SOUTH AMERICA INC.; MOMENTIVE PERFORMANCE MATERIALS USA INC.; MOMENTIVE PERFORMANCE MATERIALS WORLDWIDE INC.; MPM SILICONES, LLC
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