IP Library Granted Patent US 7,976,951
Granted Patent B2
US 7,976,951 · App. 12/466,727 · Granted Jul 12, 2011

Laminate containing an adhesive-forming composition

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Quick Facts
Patent No.
US 7,976,951
App. No.
12/466,727
Granted
Jul 12, 2011
Kind
B2
Abstract

A laminate includes a backing material coated with an adhesive composition. The adhesive composition includes a silylated polyurethane obtained from the silylation of a polyurethane prepolymer derived from the reaction of polybutadiene polyol and polyisocyanate; and an additional adhesive component.

Claims (37)

1. A laminate comprising a backing material having an adhesive layer adhered thereto, said adhesive layer being formed by curing a composition comprising:

(a) a silylated polyurethane prepolymer, the silylated polyurethane prepolymer being obtained from the silylation of a polyurethane prepolymer derived from the reaction of at least one polybutadiene polyol with at least one polyisocyanate; and,

(b) an additional adhesive component other than component (a),

wherein the backing material comprises a polymer film formed from polyethylene, polypropylene, polyester or polyimide.

2. The laminate of claim 1 wherein the polybutadiene polyol possesses a number average molecular weight of from about 500 to about 10,000.

3. The laminate of claim 1 wherein the polybutadiene polyol possesses a number average molecular weight of from about 800 to about 5,000.

4. The laminate of claim 1 wherein the polybutadiene polyol possesses a primary hydroxyl group content of from about 0.1 to about 2.0 meq/g.

5. The laminate of claim 1 wherein the polyurethane prepolymer is silylated with at least one compound selected from the group consisting of aminosilane and isocyanatosilane.

6. The laminate of claim 5 wherein the aminosilane is of the general formula:

wherein R 1 is hydrogen or an alkyl group of from about 1 to about 10 carbon atoms, R 2 is a divalent alkylene group of from about 3 to about 10 carbon atoms, R 3 and R 4 each independently is an alkyl group of from about 1 to about 6 carbon atoms or an aryl group of from about 6 to about 8 carbon atoms, and x has a value of 0, 1 or 2 and the isocyanatosilane is of the general formula:

wherein R 1 is a divalent alkylene group of from about 3 to about 10 carbon atoms, R 2 and R 3 each independently is an alkyl group of from about 1 to about 6 carbon atoms or an aryl group of from about 6 to about 8 carbon atoms, and x has a value of 0, 1 or 2.

7. The laminate of claim 1 wherein the additional adhesive component (b) is at least one adhesive selected from the group consisting of polyurethane adhesive, acrylic-based adhesive, methacrylic-based adhesive, natural rubber adhesive, synthetic rubber adhesive, polyvinylacetate adhesive, urea-formaldehyde adhesive, phenol-formaldehyde adhesive, formaldehyde resin, natural gum adhesive, silicone elastomer based adhesive, and combinations thereof.

8. The laminate of claim 1 wherein the additional adhesive component (b) is a silylated polyurethane resin.

9. The laminate of claim 7 wherein the additional adhesive component (b) is selected from the group consisting of styrene butadiene rubber adhesive, styrene isoprene styrene based adhesive, isoprene-based adhesive, methyl, low phenyl and/or high phenyl silicone-based adhesive and combinations thereof.

10. The laminate of claim 1 wherein the adhesive composition further includes at least one additional component selected from the group consisting of filler, tackifier, silane adhesion promoter, plasticizer, solvent, thixotropic agent, U.V. stabilizer, antioxidant, curing catalyst, and combination thereof.

11. The laminate of claim 10 wherein the adhesive composition includes a MQ tackifier resin containing curing catalyst therefor.

12. An article having a surface to which the laminate of claim 1 is attached.

13. The article of claim 12 wherein said article is an aircraft.

14. A laminate comprising a backing material having an adhesive layer adhered thereto, said adhesive layer being formed by curing a composition comprising:

(a) a silylated polyurethane prepolymer, the silylated polyurethane prepolymer being obtained from the silylation of a polyurethane prepolymer derived from the reaction of at least one polybutadiene polyol with at least one polyisocyanate; and,

(b) an additional adhesive component other than component (a),

wherein the laminate further includes a release liner.

15. The laminate of claim 14 wherein the release liner is fabricated from paper or a polymeric film formed from polyethylene, polyester or polyimide, and includes a release coating.

16. An article having a surface to which the laminate of claim 14 is attached.

17. A method for making a laminate comprising the steps of

(a) providing an adhesive composition including: (i) a silylated polyurethane prepolymer, the silylated polyurethane prepolymer being obtained from the silylation of a polyurethane prepolymer derived from the reaction of at least one polybutadiene polyol with at least one polyisocyanate; and, (ii) an additional adhesive component other than component (i);

(b) applying said adhesive composition to a backing material; and

(c) curing said adhesive composition to provide an adhesive layer, thereby making said laminate, wherein the backing material comprises a polymer film formed from polyethylene, polypropylene, polyester or polyimide.

18. A method for making a laminate comprising the steps of:

(a) providing an adhesive composition including: (i) a silylated polyurethane prepolymer, the silylated polyurethane prepolymer being obtained from the silylation of a polyurethane prepolymer derived from the reaction of at least one polybutadiene polyol with at least one polyisocyanate; and, an additional adhesive component other than component (i);

(b) applying said adhesive composition to a backing material; and

(c) curing said adhesive composition to provide an adhesive layer, thereby making said laminate, wherein the method further comprises applying a release liner to the adhesive layer, said release liner being removable from the laminate.

19. A method of applying a laminate to a surface of a substrate comprising the steps of:

(a) providing a laminate comprising a backing material with a layer of a cured adhesive composition in contact with at least one side of the backing material, the laminate having a release liner disposed on the layer of the cured adhesive composition; the cured adhesive composition being prepared by curing an admixture of (i) a silylated polyurethane prepolymer, the silylated polyurethane prepolymer being obtained from the silylation of a polyurethane prepolymer derived from the reaction of at least one polybutadiene polyol with at least one polyisocyanate; and, (ii) an additional adhesive component other than component (i);

(b) removing the release liner;

(c) applying the laminate to the surface of the substrate such that the layer of adhesive composition of the laminate contacts and adheres to the surface of the substrate.

20. The method of claim 19 wherein the surface of the substrate comprises a surface of an aircraft component.

Assignments (22)
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 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 →
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 →
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 →
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 →
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 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 034113/0331 →
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 →
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 →