IP Library Granted Patent US 11,760,900
Granted Patent B2
US 11,760,900 · App. 17/512,083 · Granted Sep 19, 2023

Condensation curable composition

Inventors: Hao Shen (Verona, NJ); Antonio Chaves (Chappaqua, NY); Amy Hua McKinstry (Danbury, CT); Monjit Phukan (West Harrison, NY)
Assignee: Momentive Performance Materials Inc.
C09D183/04C08F230/08C08G77/458C09D183/10C08G18/837C08G65/336
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Quick Facts
Patent No.
US 11,760,900
App. No.
17/512,083
Filed
Oct 27, 2021
Granted
Sep 19, 2023
Kind
B2
Art Unit
1765
USPC
524/588
Abstract

A moisture-curable composition is shown and described herein. The moisture-curable composition comprises a moisture-curable resin and a moisture scavenger selected from a cyanoalkylalkoxysilane. The inclusion of the cyanoalkylalkoxysilane in the moisture-curable composition has been found to effectively scavenge moisture and control the rate of curing and viscosity increase in the composition.

Claims (26)

1. A moisture-curable composition comprising:

(a) a moisture-curable resin comprising a polymer that is reactive with water, wherein the moisture-curable resin (a) is selected from a silylated polyol; a silylated polyether; a silylated polyurethane; a silane-containing copolymer derived from the copolymerization of an ethylenically unsaturated silane selected from a vinylsilane, an allylsilane, a methallylsilane, an acryloxyalkylsilane, a methacryloxyalkylsilane, and an ethylenically unsaturated monomer selected from an olefinic hydrocarbon, an acrylic acid, a methacrylic acid, an acrylate ester, a methacrylate ester, an ethylenically unsaturated dicarboxylic acid, and/or an anhydride of the ethylenically unsaturated monomer, oligomers, and/or a polymer possessing ethylenic unsaturation; a combination of two or more thereof; and

(b) a moisture scavenger selected from a cyanoalkylalkoxysilane.

2. The moisture-curable composition of claim 1 , wherein the cyanoalkylalkoxysilane is of the formula:

NC—R 1 —Si(R 2 )(R 3 )(R 4 )

where R 1 is selected from a C1-C20 bivalent hydrocarbon group; R 2 , R 3 , and R 4 are each independently selected from C1-30 monovalent hydrocarbon, a halide, and —OR 5 , where R 5 is independently selected from a C1-30 monovalent hydrocarbon, with the proviso that at least one of R 2 , R 3 , and R 4 is selected from —OR 5 .

3. The moisture-curable composition of claim 2 , wherein R 1 is selected from a C1-20 alkylene; R 2 , R 3 , and R 4 are each independently selected from a C1-20 alkyl, a C4-C20 cycloalkyl, and a C6-C30 aryl, and —OR 5 with the proviso that at least one of R 2 , R 3 , and R 4 is selected from —OR 5 ; and R 5 is independently selected from a C1-20 alkyl.

4. The moisture-curable composition of claim 2 , wherein R 1 is selected from a C1-20 alkylene; each of R 2 , R 3 , and R 4 is selected from a C1-C10 alkyl, and —OR 5 with the proviso that at least one of R 2 , R 3 , and R 4 is selected from —OR 5 , and R 5 is selected from a C1-C10 alkyl.

5. The moisture-curable composition of claim 2 , wherein R 1 is selected from a C1-C4 alkylene, and each of R 2 , R 3 , and R 4 is selected from —OR 5 , where R 5 is independently selected from a C1-C4 alkyl.

6. The moisture-curable composition of claim 1 , wherein the cyanoalkylalkoxysilane is selected from 2-cyanoethyltrimethoxysilane, 2-cyanoethyltriethoxysilane, 2-cyanoethyltripropoxysilane, 2-cyanoethyldimethoxymethylsilane, 2-cyanoethyldimethoxyethyl silane, 2-cyanoethyldiethoxymethyl silane, 2-cyanoethyldiethyoxyethyl silane, 3-cyanopropyltrimethoxysilane, 3-cyanopropyltriethoxysilane, 3-cyanopropyltripropoxysilane, 3-cyanopropyldimethoxymethyl silane, 3-cyanopropyldimethoxyethyl silane, 3-cyanodiethoxymethyl silane, 3-cyanopropyldiethoxyethylsilane, or a combination of two or more thereof.

7. The moisture-curable composition of claim 1 , wherein the cyanoalkylsiloxane is present in an amount of from about 0.1 wt. % to about 20 wt. % based on the total weight of the moisture-curable resin (a).

8. The moisture-curable composition of claim 1 , wherein the cyanoalkylsilane is present in an amount of from about 0.5 wt. % to about 10 wt. % based on the total weight of the moisture-curable resin (a).

9. The moisture-curable composition of claim 1 , wherein the moisture curable resin comprises a hydrolysable silyl group.

10. The moisture-curable composition of claim 2 , wherein the moisture-curable resin (a) is selected from a silylated polyurethane.

11. The moisture-curable composition of claim 10 , wherein the silylated polyurethane is selected from a polymer of the formula:

R z —[OC(O)NH—R 6 Si(R 7 ) x (OR 8 ) 3-x ] y

where R 1 is an organic polymer fragment, R 6 is an alkylene group of up to 12 carbon atoms, optionally containing one or more heteroatoms, each R 7 is the same or different alkyl or aryl group of up to 8 carbon atoms, each R 8 is the same or different alkyl group of up to 6 carbon atoms, x is 0, 1 or 2, and y is 1 to 6.

12. The moisture-curable composition of claim 10 , wherein R 1 is selected from a C1-C20 linear or branched bivalent hydrocarbon group; R 2 , R 3 , and R 4 are each independently selected from a C1-C10 alkyl; where R 5 is selected from a C1-C10 alkyl.

13. The moisture-curable composition of claim 10 , wherein each of R 2 , R 3 , and R 4 is selected from a C1-C20 alkyl, a C4-C20 cycloalkyl, a C6-C30 aryl, or —OR 5 .

14. The moisture-curable composition of claim 10 , wherein R 1 is selected from a C1-C20 linear or branched bivalent hydrocarbon group, and each of R 2 , R 3 , and R 4 is selected from —OR 5 , where R 5 is independently selected from a C1-C4 alkyl.

15. The moisture-curable composition of claim 1 , wherein the composition further comprises an additive selected from a pigment, a filler, a curing catalyst, a dye, a plasticizer, a thickener, a coupling agent, an extender, a solvent, a wetting agent, a tackifiers, a crosslinking agent, a thermoplastic polymer, an adhesion promoter, a UV stabilizer, or a combination of two or more thereof.

16. The moisture-curable composition of claim 1 , wherein the composition further comprises a catalyst that catalyzes the reaction of the moisture-curable resin (a) with water under curing conditions.

17. A cured composition produced by contacting the composition of claim 1 with water.

18. A moisture-curable sealant, adhesive or coating containing the moisture-curable resin composition of claim 1 .

19. A method of forming a cured composition comprising contacting the composition of claim 1 with water.

20. A method of treating a substrate comprising applying a moisture-curable composition of claim 1 to a surface of the substrate.

Assignments (5)
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 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 3, 2022
From: SHEN, HAO; CHAVES, ANTONIO; MCKINSTRY, AMY HUA; PHUKAN, MONJIT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 058527/0765 →
Continuity (1)
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