IP Library Granted Patent US 8,481,668
Granted Patent B2
US 8,481,668 · App. 11/291,235 · Granted Jul 9, 2013

Silane-containing adhesion promoter composition and sealants, adhesives and coatings containing same

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Quick Facts
Patent No.
US 8,481,668
App. No.
11/291,235
Granted
Jul 9, 2013
Kind
B2
Abstract

An adhesion promoter composition which comprises an oligomer of a functional alkoxysilane and a specific alkyl alkoxy silane is advantageously employed to improve the bonding of sealants/adhesives/coatings such as moisture curable silylated polymers on various substrates such as wet or dry concrete. In a preferred embodiment the adhesion promoter contains an octyltrialkoxysilane and an oligomer prepared from an epoxy or polyethylene oxide functional alkoxysilane.

Claims (45)

1. A composition comprising:

a) a moisture-curable silylated polymer selected from the group consisting of a silylated polyurethane polymer and polyether functionalized with terminal alkoxysilane groups; and,

b) an adhesion promoting amount of at least one adhesion promoter consisting of:

i) at least one compound having the formula 1:

R—Si(R 1 ) 3   [1]

wherein

each R 1 is independently selected from alkoxy, and R is an alkyl group having 8 carbon atoms; and,

ii) at least one oligomer prepared from a compound having formula 1:

R—Si(R 1 ) 3   [1]

wherein

each R 1 is independently selected from alkoxy, or C 1 -C 3 alkyl, with the proviso that at least two of the R 1 groups are alkoxy, and R is an organic group containing epoxy or polyethyleneoxide functionality, wherein said composition is applied to or is on a concrete substrate.

2. The composition of claim 1 wherein the moisture-curable silylated polymer is a silylated polyurethane polymer.

3. The composition of claim 1 wherein the moisture-curable silylated polymer is polyether functionalized with terminal alkoxysilane groups.

4. The composition of claim 1 wherein the R group of the oligomer (ii) is epoxycyclohexyl or glycidoxypropyl.

5. The composition of claim 4 wherein the R group is glycidoxypropyl.

6. The composition of claim 1 wherein the compound (i) is octyltriethoxysilane.

7. The composition of claim 1 wherein the R 1 groups of compound (i) or oligomer (ii) are methoxy or ethoxy.

8. The composition of claim 1 wherein the oligomer (ii) is prepared from a compound selected from the group consisting of beta (3,4-epoxycyclohexyl)ethyltriethoxysilane, gamma-glycidoxypropyltriethoxysilane, gamma-glycidoxypropyl triethoxysilane, gamma-glycidoxypropylmethyldiethoxysilane and poly(ethyleneoxide)trimethoxysilane.

9. The composition of claim 1 wherein the adhesion promoter composition consists of at least one compound (i) in the range of 40 to 95 weight percent and the oligomer (ii) in the range of 5 to 60 weight percent based upon the total weight of components (i) and (ii).

10. The composition of claim 1 further comprising one or more component selected from the group consisting of plasticizers, fillers, UV stabilizers, thixotropes, colorants, moisture scavengers and catalysts.

11. A method for treating a substrate comprising:

a) providing a composition containing a moisture-curable silylated resin selected from the group consisting of a silylated polyurethane polymer and polyether functionalized with terminal alkoxysilane groups and an adhesion promoter, the adhesion promoter including,

i) at least one compound having the formula 1:

R—Si(R 1 ) 3   [1]

wherein

each R 1 is alkoxy, and

R is alkyl having from 8 carbon atoms; and,

ii) at least one oligomer prepared from a compound having formula 1:

R—Si(R 1 ) 3   [1]

wherein

each R 1 is independently selected from alkoxy, or C 1 -C 3 alkyl, with the proviso that at least two of the R 1 groups is alkoxy, and R is an organic group containing epoxy or polyethyleneoxide functionality; and

b) applying said composition to a surface of the substrate, wherein said substrate is concrete.

12. The method of claim 11 wherein the substrate has a pH of above 10.

13. The composition of claim 1 wherein the composition is a sealant, coating or adhesive.

14. A sealant, adhesive or coating composition comprising:

a) a moisture-curable moisture-curable silylated polymer selected from the group consisting of a silylated polyurethane polymer and polyether functionalized with terminal alkoxysilane groups; and,

b) an adhesion promoting amount of at least one adhesion promoter consisting of:

i) 40% to 95% by weight based upon the total weight of components (i) and (ii) of at least one compound having the formula 1:

R—Si(R 1 ) 3   [1]

wherein

each R 1 is independently selected from alkoxy, or C 1 -C 3 alkyl, with the proviso that at least two of the R 1 groups is alkoxy, and R is an alkyl group having from 8 to 20 carbon atoms; and,

ii) 5% to 60% by weight based upon the total weight of components (i) and (ii) of at least one oligomer prepared from a compound having formula 1:

R—Si(R 1 ) 3   [1]

wherein

each R 1 is independently selected from alkoxy, or C 1 -C 3 alkyl, with the proviso that at least two of the R 1 groups are alkoxy, and R is an organic group containing epoxy or polyethyleneoxide functionality, wherein said sealant, adhesive or coating composition is applied to or is on a concrete substrate.

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.
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 →
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
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
To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
Reel/Frame 054387/0001 →
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 →
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 →
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 - 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 →
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.
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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.
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PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
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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 Feb 21, 2008
From: GENERAL ELECTRIC COMPANY
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Reel/Frame 020542/0607 →
SECURITY AGREEMENT Recorded Jul 3, 2007
From: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 019511/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2006
From: GAUTHIER, REMY; LACROIX, CHRISTINE
To: GENERAL ELECTRIC COMPANY
Reel/Frame 017367/0670 →