IP Library Granted Patent US 8,247,079
Granted Patent B2
US 8,247,079 · App. 12/381,039 · Granted Aug 21, 2012

Laminate containing a silylated polyurethane adhesive composition

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Quick Facts
Patent No.
US 8,247,079
App. No.
12/381,039
Granted
Aug 21, 2012
Kind
B2
Abstract

A laminate includes a backing material coated with an adhesive composition. The adhesive composition includes a cured silylated polyurethane composition derived from polyester based polyurethane prepolymer. The silylated polyurethane composition when partially silylated is especially useful for pressure sensitive adhesives where it imparts superior adhesive and cohesive performance thereto.

Claims (24)

1. A laminate comprising a backing material having a cured pressure sensitive adhesive composition applied thereto, the adhesive composition including a silylated polyurethane prepolymer prepared from a process which comprises:

(a) reacting a polyol being a blend of two or more polyester polyols possessing an average of hydroxyl group of the blend ranging from about 2.05 to about 2.75 with at least one polyisocyanate in the presence of a catalyst at a molar ratio of NCO to OH from about 0.3 to about 0.95 to provide a hydroxyl-terminated polyurethane prepolymer,

(b) reacting said hydroxyl-terminated polyurethane prepolymer with an isocyanatosilane to form said silylated polyurethane prepolymer,

wherein less than 95% of the hydroxyl-terminated polyurethane prepolymer is silylated, and

wherein the weight percent of Si in the silylated polyurethane prepolymer is from 0.098% to 0.118%,

with the proviso that if said polyester polyol comprises a crystalline polyester diol, said diol has a melting point of less than 50° C.

2. The laminate of claim 1 wherein the adhesive composition further comprises an additional adhesive component.

3. The laminate of claim 2 where in the additional adhesive component is at least one adhesive derived from a polymer selected from the group consisting of silane-terminated polyurethane, polyurethane, silicone, natural rubber, styrene butadiene rubber, styrene isoprene styrene, acrylic, isoprene and polyisobutylene.

4. The laminate of claim 1 wherein said isocyanatosilane is of the general formula:

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

5. The laminate of claim 1 wherein the adhesive composition 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 and curing catalyst.

6. The laminate of claim 5 wherein the adhesive composition includes an MQ tackifier resin containing curing catalyst therefor.

7. The laminate of claim 1 wherein the backing material comprises a polymeric film formed from polyethylene, polypropylene, polyester, or polyimide.

8. The laminate of claim 1 further including a release liner that is removably attached to the cured adhesive composition.

9. The laminate of claim 8 wherein the release liner is fabricated from paper or a polymeric film formed from polyethylene, polypropylene, polyester, or polyimide, and includes a silicone release coating.

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

11. The article of claim 10 wherein said article is an aircraft.

12. The laminate of claim 1 , wherein said catalyst is dimethyltinbis[(1-oxoneodecyl)oxyl]stannane.

13. A laminate comprising a backing material having a cured pressure sensitive adhesive composition applied thereto,

the adhesive composition including a silylated polyurethane prepolymer prepared from a process which comprises:

(a) reacting a polyol being a blend of two or more polyester polyols possessing an average of hydroxyl group of the blend ranging from about 2.05 to about 2.75 with at least one polyisocyanate in the presence of a catalyst at a molar ratio of NCO to OH from about 0.3 to about 0.95 to provide a hydroxyl-terminated polyurethane prepolymer,

(b) reacting said hydroxyl-terminated polyurethane prepolymer with an isocyanatosilane to form said silylated polyurethane prepolymer,

wherein less than 95% of the hydroxyl-terminated polyurethane prepolymer is silylated, and

wherein said polyester polyol comprises a crystalline polyester polyol having a melting point of less than 50° C.

Assignments (24)
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 →
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 →
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 →
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 034113/0252 →
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 Jul 1, 2009
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
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 022902/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 28, 2009
From: GRISWOLD, ROY M.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 022753/0899 →