Non-metal catalyzed room temperature moisture curable organopolysiloxane compositions

Patent metadata

Field	Value
Publication number	US-2016130404-A1
Application number	US-201414890189-A
Country	US
Kind code	A1
Filing date	May 9, 2014
Priority date	May 10, 2013
Publication date	May 12, 2016
Grant date	—

Abstract

The present invention provides curable compositions that are free of metal catalysts including both tin and non-tin metal catalysts. The curable compositions employ a catalyst comprising curable polymers having reactive terminal silyl groups. In particular, a silylated carboxylic acid is an alternative to organotin or other metal catalysts. In addition, the catalyst may be used with an amino-containing adhesion promoter or a mixture of amine-containing adhesion promoters and an amino-containing siloxane. The combination of these materials accelerates the condensation curing of moisture curable silicones/non-silicones even in the absence of a metal-based catalyst.

First claim

1 . A composition for forming a cured polymer composition comprising:
(A) a polymer having at least a reactive silyl group; (B) a crosslinker or chain extender chosen from an alkoxysilane, an alkoxysiloxane, an oximosilane, an oximosiloxane, an enoxysilane, an enoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkarylaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof; (C) a catalyst composition comprising a silylated carboxylic acid compound; (D) an adhesion promoter; (E) optionally a cure accelerator; and (F) optionally a flow modifier or extender.

2 . The composition of claim 1 , wherein the silylated carboxylic acid is a silyl ester of a carboxylic acid comprising a silyl group bonded to a carboxylic acid compound.

3 . The composition of claim 2 , wherein the carboxylic acid compound of the silylated carboxylic acid is chosen from an aliphatic carboxylic acid, an unsaturated carboxylic acid, or a combination of two or more thereof.

4 . The composition of claim 2 , wherein the carboxylic acid compound of the silylated carboxylic acid is chosen from a linear or branched C 4 -C 30 -alkyl carboxylic acid, or a combination of two or more such carboxylic acids.

5 . The composition of claim 1 , wherein the carboxylic acid compound is chosen from undecenoic acid, dodecenoic acid, tridecenoic acid, tetradecenoic acid, pentadecenoic acid, hexadecenoic acid, heptadecenoic acid, octadecenoic acid, nonadecenoic acid, eicosenoic acid, docosenoic acid, tetracosenoic acid, or a combination of two or more thereof.

6 . The composition of claim 1 , wherein the silyl group is an alkyl silyl group, an alkoxy silyl group, or a combination thereof.

7 . The composition of claim 1 , wherein the silyl group is a trialkyl silyl group comprising alkyl groups having 1 to 10 carbon atoms.

8 . The composition of claim 1 , wherein the catalyst composition comprises a trimethylsilyl ester of undecenoic acid.

9 . The composition of claim 1 , wherein the silylated carboxylic acid is of the formula:

where R 11 is CH 3 , an alkene, or a siloxane group of formula —((CH 3 ) 3 Si—O) 2 —Si(CH3); R 12 , R 13 , and R 14 are independently chosen from a C 1 -C 10 alkyl, polysiloxane, an alkoxy group of the formula OR 15 , where R 15 is a C 1 -C 10 alkyl group; and t is 4-30.

10 . The composition of claim 1 , wherein the silylated carboxylic acid is of the formula:

11 . The composition of claim 1 comprising from about 0.005 to about 7 pt. wt. of the catalyst composition (C) per 100 pt. wt. of component (A).

12 . The composition of claim 1 comprising from about 0.1 to about 5 pt. wt. of the silylated carboxylic acid compound (C) per 100 pt. wt. of component (A).

13 . The composition of claim 1 , wherein the adhesion promoter (D) includes an amino silane functional compound and/or an organic amine.

14 . The composition of claim 1 , wherein the adhesion promoter (D) is chosen from an (aminoalkyl)trialkoxysilane, an (aminoalkyl)alkyldialkoxysilane, a bis(trialkoxysilylalkyl)amine, a tris(trialkoxysilylalkyl)amine, a tris(trialkoxysilylalkyl)cyanurate, and a tris(trialkoxysilylalkyl)isocyanurate, an (epoxyalkyl)alkyldialkoxysilane, an (epoxyalkyl)trialkoxysilane, an (epoxyalkylether)trialkoxysilane, or a combination of two or more thereof.

15 . The composition of claim 1 further comprising from about 0.1 to about 5 pt. wt. of amino-containing adhesion promoter (D) per 100 pt. wt. of component (A).

16 . The composition of claim 1 comprising from about 0.1 to about 5 pt. wt. of an amino-functional siloxane component (E) per 100 pt. wt. of component (A).

17 . The polymer composition of claim 1 , wherein the polymer (A) has the formula (2)
[R 1 a R 2 3-a Si—Z—] n —X—Z—SiR 1 a R 2 3-a   (2)

where X is chosen from a polyurethane; a polyester; a polyether; a polycarbonate; a polyolefin; a polypropylene; a polyesterether; and a polyorganosiloxane having units of R 3 SiO 1/2 , R 2 SiO, RSiO 3/2 , and/or SiO 4/2 ,
n is 0 to 100,
a is 0 to 2,
R 1 can be identical or different at the same Si-atom and chosen from a C 1 -C 10 -alkyl; a C 1 -C 10 alkyl substituted with one or more of Cl, F, N, O or S; a phenyl; a C 7 -C 16 alkylaryl; a C 7 -C 16 arylalkyl; a C 2 -C 4 polyalkylene ether; or a combination of two or more thereof,
R 2 is chosen from OH, a C 1 -C 8 -alkoxy, a C 2 -C 18 -alkoxyalkyl, an oximoalkyl, an enoxyalkyl, an aminoalkyl, a carboxyalkyl, an amidoalkyl, an amidoaryl, a carbamatoalkyl, or a combination of two or more thereof, and
Z is a bond, a divalent unit selected from the group of a C 1 -C 8 alkylene, or O.

18 . The composition of claim 1 , wherein the cross-linker component (B) is chosen from a silane or a siloxane, the silane or siloxane having two or more reactive groups that can undergo hydrolysis and/or condensation reaction with polymer (A) or on its own in the presence of water and component (F).

19 . The composition of claim 1 wherein the cross-linker component (B) is chosen from tetraethylorthosilicate (TEOS); a polycondensate of TEOS; methyltrimethoxysilane (MTMS); vinyl-trimethoxysilane; methylvinyldimethoxysilane; dimethyldiethoxysilane; vinyltriethoxysilane; tetra-n-propylorthosilicate; vinyltris(methylethylketoxime)silane; methyltris(methylethylketoxime)silane; trisacetamidomethylsilane; bisacetamidodimethylsilane; tris(N-methyl-acetamido)methylsilane; bis(N-methylacetamido)dimethylsilane; (N-methyl-acetamido)methyldialkoxysilane; trisbenzamidomethylsilane; trispropenoxymethylsilane; alkyldialkoxyamidosilanes; alkylalkoxybisamidosilanes; CH 3 Si(OC 2 H 5 ) 1-2 (NHCOR) 2-1 ; (CH 3 Si(OC 2 H 5 )(NCH 3 COC 6 H 5 ) 2 ; CH 3 Si(OC 2 H 5 )—(NHCOC 6 H 5 ) 2 ; methyldimethoxy(ethylmethylketoximo)silane; methylmethoxybis-(ethylmethylketoximo)silane; methyldimethoxy(acetaldoximo)silane; methyldimethoxy(N-methylcarbamato)silane; ethyldimethoxy(N-methylcarbamato)silane; methyldimethoxyisopropenoxysilane; trimethoxyisopropenoxysilane; methyltri-iso-propenoxysilane; methyldimethoxy(but-2-ene-2-oxy)silane; methyldimethoxy(1-phenylethenoxy)silane; methyldimethoxy-2(1-carboethoxypropenoxy)silane; methylmethoxydi-N-methylaminosilane; vinyldimethoxymethylaminosilane; tetra-N,N-diethylaminosilane; methyldimethoxymethylaminosilane; methyltricyclohexylaminosilane; methyldimethoxyethylaminosilane; dimethyldi-N,N-dimethylaminosilane; methyldimethoxyisopropylaminosilane dimethyldi-N,N-diethylaminosilane. ethyldimethoxy(N-ethylpropionamido)silane; methyldimethoxy(N-methylacetamido)silane; methyltris(N-methylacetamido)silane; ethyldimethoxy(N-methylacetamido)silane; methyltris(N-methylbenzamido)silane; methylmethoxybis(N-methylacetamido)silane; methyldimethoxy(caprolactamo)silane; trimethoxy(N-methylacetamido)silane; methyldimethoxyethylacetimidatosilane; methyldimethoxypropylacetimidatosilane; methyldimethoxy(N,N′,N′-trimethylureido)silane; methyldimethoxy(N-allyl-N′,N′-dimethylureido)silane; methyldimethoxy(N-phenyl-N′,N′-dimethylureido)silane; methyldimethoxyisocyanatosilane; dimethoxydiisocyanatosilane; methyldimethoxythioisocyanatosilane; methylmethoxydithioisocyanatosilane, or a combination of two or more thereof.

2

Assignees

• Momentive Performance Mat Inc

Inventors

• Patel Mihirkumar Maheshbai
• Dhanabalan Anantharaman
• Dinkar Sumi
• Sarkar Alok

Classifications

• C08G77/44 Primary

  containing only polysiloxane sequences · CPC title

• C08K5/544 Primary

  containing nitrogen · CPC title

• C08L101/10

  containing hydrolysable silane groups · CPC title

• C08G77/08

  characterised by the catalysts used · CPC title

• C08K5/5419

  containing at least one Si—C bond · CPC title