Moisture curable compositions

Patent metadata

Field	Value
Publication number	US-2017306096-A1
Application number	US-201515528114-A
Country	US
Kind code	A1
Filing date	Nov 20, 2015
Priority date	Nov 20, 2014
Publication date	Oct 26, 2017
Grant date	—

Abstract

The present invention provides moisture-curable compositions comprising an amino ester catalyst as an alternative to organotin catalysts. In particular, the present invention provides a condensation catalyst comprising a secondary amine, a tertiary amine, a substituted amine (e.g., an amino ester compound), or a combination of two or more thereof and optionally one or more aminosilanes or siloxanes. Further, the compositions employing amino esters allow for tuning or adjusting the cure characteristics of the compositions by the addition of other components such as adhesion promoters or acidic compounds, and provides good adhesion and storage stability.

First claim

1 . A composition for forming a curable polymer composition comprising:
(A) a polymer having at least a reactive silyl group; (B) a crosslinker or chain extender; (C) a catalyst comprising an amine compound chosen from a secondary amine, a tertiary amine, a substituted amine, or a combination thereof; (D) optionally at least one amino-containing adhesion promoter; (E) optionally a filler component; (F) optionally a acidic component; and (G) optionally an auxiliary component comprising an organo-functional silicon compound and or low molecular weight organic polymer and or high boiling solvents.

2 . The composition of claim 1 , wherein the composition is a two-part composition comprising:
(i) a first portion comprising the polymer (A), optionally the filler component (E), and optionally the acidic compound (F); and (ii) a second portion comprising the crosslinker (B), the catalyst (C), optionally the adhesion promoter (D), and optionally an organo-functional silicon compound and/or low molecular weight organic polymer or high boiling solvents (G), whereby (i) and (ii) are stored separately until applied for curing by mixing of the components (i) and (ii).

3 . The composition of claim 1 , wherein the composition is a two-part composition comprising:
(i) a first portion comprising the polymer (A), the crosslinker (B), optionally the filler component (E), and optionally the acidic compound (F); and (ii) a second portion comprising the catalyst (C), optionally an organo-functional silicon compound and/or low molecular weight organic polymer or high boiling solvents (G), whereby (i) and (ii) are stored separately until applied for curing by mixing of the components (i) and (ii).

4 . The composition of claim 1 , wherein the catalyst comprises a plurality of amine functional groups.

5 . The composition of claim 1 , wherein the amine compound comprises one or multiple amine functional group of the formula:

where R 22 is independently chosen from hydrogen; a C 1 -C 15 linear, branched, or cyclic alkyl group; a C 1 -C 15 linear, branched, or cyclic alkyl group comprising one or more substituents chosen from a halide, N, O or S; a C 6 -C 10 aryl group; a C 7 -C 16 linear or branched alkylaryl group; a C 2 -C 4 polyalkylene ether; or a linear or branched C 7 -C 16 heteroaralkyl, heteroalkyl, heterocycloalkyl, or heteroaryl; and
where R 23 and R 24 are independently chosen from a C 1 -C 15 linear, branched, or cyclic alkyl group; a C 1 -C 15 linear, branched, or cyclic alkyl group comprising one or more substituents chosen from a halide, N, O or S; a C 6 -C 10 aryl group; a C 7 -C 16 linear or branched alkylaryl group; a C 2 -C 4 polyalkylene ether; a linear or branched C 7 -C 16 heteroaralkyl; heteroalkyl, heterocycloalkyl, heteroaryl, with the proviso that the N atom is bi-substituted with either of R 23 , R 24 , R 23 and R 24 , or a combined R 23 , R 24 in the compound.

6 . The composition of claim 1 , wherein the catalyst comprises a secondary amine selected from dialkyl and substituted dialkyl amines, dimethylamine, diisopropylamine, dibutylamine, N-methylbutylamine, N,N-diallyl trimethylenediamine, diamylamine, dihexylamine, dioctylamine, N-ethylcetylamine, didodecylamine, ditetradecylamine, diricinoleylamine, N-isopropylstearylamine, N-isoamylhexylamine, N-ethyloctylamine, dioctadecylamine, their homologs and analogs, or a combination of two or more thereof.

7 . The composition of claim 1 , wherein the catalyst comprises a secondary cycloalkylamine selected from dicyclohexylamine, N-methylcyclohexylamine, dicyclopentylamine, N-octylcyclohexylamine, N-octyl-3,5,5-trimethylcyclohexylamine, diallylamine, N-ethylallylamine, N-octylallylamine, dioleylamine, N-isopropylolelyamine, N-methyl-3,3,5-trimethyl-5-cyclohexenylamine, N-amyl-linoleylamine, N-methyl-propargylamine, diphenylamine, their analogs and homologs, or a combination of two or more thereof.

8 . The composition of claim 1 , wherein the catalyst comprises a tertiary amine selected from triethylamine, tri-isopropylamine, tributylamine, N-ethyldibutylamine, N-ethyl-N-butylamylamine, N,N-diethyl aniline, triallylamine, N,N-dipropylcyclohexylamine, N,N-dipropyloleyl-amine, trimethylamine, N-octyldiallylamine, N,N-dipropylcyclohexylamine, dimethylaminopropylemine, dimethylaminoethoxypropylamine, pentamethyldiethylylenetriamine, trimethylamine, triethylamine, N-methylmorpholine, N-ethylmorpholine, N,N-dimethylbenzylamine, N,N-dimethylethanolamine, N,N,N′,N′-tetramethyl- 1,4-butanediamine, N,N-dimethylpiperazine, bis(2-dimethylaminoethyl)ether, morpholine, N-substituted morpholines, such as N-methyl or N-ethyl morpholine, 4,4′-(oxydi-2,1-ethanediyl)bis, triethylenediamine, pentamethyl diethylene triamine, dimethyl cyclohexyl amine, N-cetyl N,N-dimethyl amine, N-coco-morpholine, N,N-dimethyl aminomethyl N-methyl ethanol amine, N,N,N′-trimethyl-N′-hydroxyethyl bis(aminoethyl)ether, N,N-bis(3-dimethylaminopropyl)N-isopropanolamine, (N,N-dimethyl)amino-ethoxy ethanol, N,N,N′,N′-tetramethyl hexane diamine, N,N-dimorpholinodiethyl ether, N-methyl imidazole, dimethyl aminopropyl dipropanolamine, bis(dimethylaminopropyl)amino-2-propanol, tetramethylamino bis (propylamine), (dimethyl(aminoethoxyethyl))((dimethyl amine)ethyl)ether, tris(dimethylamino propyl) amine, dicyclohexyl methyl amine, bis(N,N-dimethyl-3-aminopropyl) amine, N,N-bis (3-dimethylaminopropyl)-N-isopropanolamine, 1,3-propanediamine, 1,2-ethylene piperidine, methyl-hydroxyethyl piperazine, dimethylaminopropyl-S-triazine, bisdimethylaminopropylurea, their analogs and homologs, or a combination of two or more thereof.

9 . The composition of claim 1 , wherein the catalyst comprises a heterocyclic amine selected from piperidine, pyridine, methylpiperazine, 2,2,4,6-tetramethylpiperidine, 2,2,4,6-tetramethyl-tetrahydropyridine, N-ethyl 2,2,4,6 tetramethylpiperidine, 2-aminopyrimidine, 2-aminopyridine, 2-(dimethylamino)pyridine, 4-(dimethylamino)pyridine, 2-hydroxypyridine, imidazole, 2-ethyl-4-methylimidazole, morpholine, N-methylmorpholine, 2-piperidinemethanol, 2-(2-piperidino)ethanol, piperidone, 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine, aziridine, methoymethyldiphenylamine, nicotine, pentobarbital, methadone, cocaine, and triphenylamine, or a combination of two or more thereof.

10 . The composition of claim 1 , wherein the catalyst comprises a substituted amine is chosen from an amino ester compound.

11 . The composition of claim 10 , wherein the amino ester compound comprises at least one amino ester functional group.

12 . The composition of claim 10 , wherein the amino ester compound comprises 1-10 amino ester functional groups.

13 . The composition of claim 10 , wherein the amino ester compound comprises 1-4 amino ester functional groups.

14 . The composition of claim 10 , wherein the amino ester compound comprises an amino ester functional group of the formula:

where R 17 is a C 1 -C 5 alkyl group, and R 18 and R 19 are independently chosen from hydrogen, a C 1 -C 10 linear, branched, or cyclic alkyl group, a C 1 -C 10 linear, branched, or cyclic alkyl group comprising one or more substituents chosen from a halide, N, O or S; a C 6 -C 10 aryl group; a C 7 -C 16 alkylaryl group; a C 7 -C 16 arylalkyl group; a C 2 -C 4 polyalkylene ether; a substituted silicon, a substituted siloxane, or a combination of two or more thereof.

15 . The composition of

Assignees

• Momentive Performance Mat Inc

Inventors

• Muthusamy Ramesh
• Dinkar Sumi
• Dhanabalan Anantharaman

Classifications

• C08K5/544

  containing nitrogen · CPC title

• C07C229/24

  having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid · CPC title

• C08G77/08 Primary

  characterised by the catalysts used · CPC title

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title

• C08K5/175

  containing COOH-groups; Esters or salts thereof · CPC title