IP Library Granted Patent US 8,343,632
Granted Patent B2
US 8,343,632 · App. 12/907,281 · Granted Jan 1, 2013

Paper release compositions having improved adhesion to paper and polymeric films

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Quick Facts
Patent No.
US 8,343,632
App. No.
12/907,281
Filed
Oct 19, 2010
Granted
Jan 1, 2013
Kind
B2
Art Unit
1761
USPC
428/447
Abstract

The present invention relates to curable alkenyl based silicone release coating compositions having improved adhesion to paper and polymeric substrates. Furthermore the present invention relates to the process for making a silicone release coating with improved adhesion to paper and polymeric substrates.

Claims (37)

1. A laminate having a substrate and a cured release coating on said substrate,

wherein said substrate is a polyester film and wherein

said cured release coating is the cured product of a release coating composition comprising:

(A) an additive for anchorage of a release coating, said additive being a compound of the general formula:

(R a SiO( 4−a )/ 2 ) n

where n is an integer greater than 3, a ranges from about 1 to about 3, R is independently selected from the group consisting of: oxirane containing radicals having from one to forty carbon atoms, epoxide containing radicals having from one to forty carbon atoms, carboxylic acid anhydride containing radicals having from one to forty carbon atoms, monovalent hydrocarbon radicals, monovalent hydrocarbonoxy radicals, and hydride atoms, wherein at least one of said oxirane or epoxide or carboxylic acid anhydride containing radicals are present per molecule, and wherein at least one of said hydride atoms are present per molecule;

(B) a curable alkenyl silicone having the formula

M Vi a T b D c M d where

M Vi =R 1 3−p R 2 p SiO 1/2 , where R 1 is selected from the group consisting of trifluoropropyl and one to forty carbon monovalent hydrocarbon radicals and R 2 is selected from the group consisting of two to forty carbon atom terminal olefinic monovalent hydrocarbon radicals, where p ranges from 1 to 3;

T=R 3 SiO 3/2 where R 3 is selected from the group consisting of R 1 and R 2 ;

D=R 4 R 5 SiO 2/2 where R 4 and R 5 are each independently selected from the group consisting of R 1 and R 2 ; and

M=R 1 3 SiO 1/2 where each R 1 is as previously defined and is independently selected; wherein a and b have values ranging from 2 to 5, c is an integer ranging from about 50 to about 1,000 and d has a value ranging from 2 to about 0.5;

(C) a hydrogen siloxane selected from the group of compounds;

MD e D′ f M,

MD′ f M,

MD e D′ f M′,

M′D e D′ f M, and

M′D e M′, where

M=R′ 3 SiO 1/2 ,

M′=H g R′ 3−g SiO 1/2 , and

D=R′R′SiO 2/2 , and

D′=R′HSiO 2/2 wherein each R′ in M, M′, D, and D′ is independently selected from the group consisting of trifluoropropyl and one to forty carbon monovalent hydrocarbon radicals wherein the subscripts e and f may be zero or positive whereby the sum of e and f ranges from about 10 to about 100 subject to the limitation that the sum of f and g is two or greater;

(D) a hydrosilylation catalyst; and

(E) an inhibitor.

2. The laminate of claim 1 wherein the viscosity of component (B) of the release coating ranges from about 125 to about 1,000 centipoise.

3. The laminate of claim 1 wherein at least one of said oxirane or epoxide containing radicals and at least one of said hydride atoms are present per molecule of said component (A) of said release coating.

4. The laminate of claim 1 , wherein at least one of said carboxylic acid anhydride containing radicals and at least one of said hydride atoms are present per molecule of said component (A) of said release coating.

5. The laminate of claim 1 wherein variable a of component (A) of the release coating is about 3, and component (A) features at least one of said oxirane or epoxide containing radicals per molecule, at least one of said hydride atoms per molecule, and at least one of said hydrocarbonoxy radicals per molecule.

6. The laminate of claim 1 wherein the subscripts a, b and d of component (B) of the release coating satisfy the relationship a+d>b.

7. The laminate of claim 6 wherein the viscosity of component (B) of the release coating ranges from about 100 to about 10,000 centipoise.

8. The laminate of claim 1 where R 1 is methyl or phenyl and R 2 is selected from the group consisting of two to ten carbon atom alkenyl groups.

9. The laminate of claim 1 wherein where R′ is methyl or phenyl.

10. The laminate of claim 1 wherein the hydrogen siloxane is selected from the groups consisting of

MD e D′ f M,

MD′ f M,

and mixtures thereof, wherein the subscripts e and f may be zero or positive whereby the sum of e and f ranges from about 10 to about 100 subject to the limitation that f is two or greater.

11. The laminate of claim 1 wherein the release coating composition further comprises at least one component selected from the group consisting of bath life extenders, release additives, fillers, extenders, photocatalysts, reactive diluents, and anchorage additives.

Assignments (20)
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 063548/0281 →
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 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
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 →
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 →
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 034066/0570 →
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 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 →