Moisture curable composition with amino acids

Patent metadata

Field	Value
Publication number	US-2016200880-A1
Application number	US-201414914887-A
Country	US
Kind code	A1
Filing date	Aug 29, 2014
Priority date	Aug 30, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

The present invention provides curable compositions comprising non-tin metal accelerators that accelerate the condensation curing of moisture-curable silicones/non-silicones. In particular, the present invention provides an accelerator comprising amino acid compounds that are suitable as replacements for organotin in sealant and RTV formulations.

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; and (C) a condensation accelerator comprising an amino acid compound.

2 . The composition of claim 1 , wherein the amino acid compound comprises at least one group attached to the N-terminus that is a group other than hydrogen.

3 . The composition of claim 1 , wherein the amino acid compound comprises an amino acid substituted at the O-terminus with a group other than hydrogen.

4 . The composition of claim 1 , wherein the amino acid compound comprises a compound of the formula (6):

wherein Q is selected from

an aliphatic heterocyclic compound containing at least one nitrogen atom of the formula:

where t is an integer from 1 to 6;
or an aromatic heterocyclic compound containing at least one nitrogen atom;
where R 9 , R 10 , and R 11 are independently selected from hydrogen, a linear or branched alkyl, a linear or branched heteroalkyl, an aryl, a heteroaryl, a cycloalkyl, a heterocycloalkyl, a linear or branched aralkyl, or a linear or branched heteroaralkyl, a silyl group, as siloxy group, or a combination of two or more thereof;
R 12 and R 13 are independently selected from hydrogen, a linear or branched alkyl, a cycloalkyl, an aryl, a heteroaryl, a linear or branched aralkyl, a linear or branched heteroaralkyl, a silyl group, a siloxy group, a functional group of the formula,

or a functional group of the formula

where X is either O or S; and R 14 and R 15 are independently selected from hydrogen, a linear or branched alkyl, a cycloalkyl, an aryl, a heteroaryl, a linear or branched aralkyl, a linear or branched heteroaralkyl, OR 16 , NR 2 16 , or SR 16 ; and R 16 is chosen from hydrogen, a linear or branched alkyl, a cycloalkyl, an aryl, a heteroaryl, a linear or branched aralkyl, a linear or branched heteroaralkyl, an acyl group, a thioacyl group, or a combination of two or more thereof, and R 16 groups may be similar or different.

5 . The composition of claim 4 , wherein R 9 is a group other than hydrogen, R 12 is a group other than hydrogen, or both R 9 and R 12 is a group other than hydrogen.

6 . The composition of claim 4 , wherein at least one of R 12 and R 13 is chosen from a functional group of the formula:

7 . The composition of claim 6 , wherein X is O, and R 14 is a C 1 -C 6 alkyl group.

8 . The composition of claim 6 , wherein R 12 is an acetyl.

9 . The composition of claim 1 , wherein the amino acid comprises a compound of the formula:

10 . The composition of claim 1 , wherein the amino acid is chosen from N-acetyl-glycine, N-acetyl-alanine, N-acetyl-valine, N-acetyl-leucine, N-acetyl-isoleucine, N-acetyl-serine, N-acetyl-threonine, N-acetyl-cysteine, N-acetyl-methionine, N-acetyl-aspartic acid, N-acetyl-asparagine, N-acetyl-glutamic acid, N-acetyl-glutamine, N-acetyl-arginine, N-acetyl-lysine, N-acetyl-histidine, N-acetyl-phenylalanine, N-acetyl-tyrosine, N-acetyl-tryptophan, N-acetyl-proline, N-acetyl-taurine, N-acetyl-hydroxyproline, N-acetyl-canavanine, N-acetyl-hydroxylysine, N-acetyl-cycloserine, N-acetyl-homoarginine, N-acetyl-norleucine, N-acetyl-norvaline, N-acetyl-homoserine, N-acetyl-methylserine, N-acetyl-hydroxyvaline, N-acetyl-ethionine, N-acetyl-methoxinine, N-acetyl-β-aminoisobutanoic acid, N-acetyl-homocysteine, N-acetyl-cysteine sulfinic acid, N-acetyl-homophenylalanine, N-acetyl-homotryptophan, N-acetyl-hydroxytryptamine (N-acetylserotonin), N-acetyl-tryptamine, N-acetyl-ornithine, N-acetyl-citrulline, N-acetyl-argininosuccinic acid, N-acetyl-dopa, N-acetyl-3-iodotyrosine, N-acetyl-3,5-diiodotyrosine, N-acetyl-3,5,3′-triiodothyronine, N-acetyl-thyroxine, N-acetyl-creatine, N-acetyl-creatinine, N-acetyl-cystine and N-acetyl-homocystine, or a combination of two or more thereof.

11 . The composition of claim 1 , wherein the amino acid compound is chosen from glycine trimethylsilyl ester, alanine trimethylsilyl ester, d-alanine trimethylsilyl ester, glycine tert-butyldimethylsilyl ester, 1-serine trimethylsilyl ester, valine trimethylsilyl ester, norvaline trimethylsilyl ester, isoleucine trimethylsilyl ester, 1H-imidazole-1-acetic acid trimethylsilyl ester, 2-pyridinecarboxylic acid trimethylsilyl ester, proline trimethylsilyl ester, 2-piperidinecarboxylic acid trimethylsilyl ester, or a combination of two or more thereof.

12 . The composition of claim 1 , wherein the amino acid compound is chosen from N-acetyl-glycine trimethylsilyl ester, N-(trifluoroacetyl)-1-leucine trimethylsilyl ester, or a combination of two or more thereof.

13 . The composition of claim 1 , wherein the amino acid compound is chosen from 2-methyl-(N-(trimethylsilyl)-alanine trimethylsilyl ester, S-ethyl-N-(trimethylsilyl)-homocysteine trimethylsilyl ester, 1-(trimethylsilyl)-1H-indole2-carboxylic acid trimethylsilyl ester, or a combination of two or more thereof.

14 . The composition of claim 1 , wherein the amino acid compound is chosen from 2-[bis(trimethylsilyl)amino]-butanoic acid trimethylsilyl ester, or a combination of two or more thereof.

15 . The composition of claim 1 , wherein the amino acid compound is chosen from glycine bis(trimethylsiloxy)methylsilyl ester, alanine bis(trimethylsiloxy)methylsilyl ester, valine bis(trimethylsiloxy)methylsilyl ester, leucine bis(trimethylsiloxy)methylsilyl ester, glycine dimethyl(trimethylsiloxy)silyl ester, alanine dimethyl(trimethylsiloxy)silyl ester, valine dimethyl(trimethylsiloxy)silyl ester, leucine dimethyl(trimethylsiloxy)silyl ester, or a combination of two or more thereof.

16 . The composition of claim 1 , wherein the amino acid compound comprises N-acetyl-proline.

17 . The composition of claim 1 comprising from about 0.001 to about 10 parts per weight of accelerator (C) per 100 parts per weight of the polymer (A).

18 . The composition of claim 1 comprising from about 0.1 to about 5 wt. pt. of accelerator (C) per 100 parts of the polymer A.

19 . The composition of claim 1 , wherein the accelerator (C) is substantially free of tin.

20 . The composition of claim 1 , wherein the accelerator (C) further comprises a blend of metal accelerator, a salt of a metal accelerator, a carboxylic acid, an alkyl-sulfonic acid, an aryl sulfonic acid, an inorganic acid, an amine, a guanidine, an amidine, an inorganic base, or a combination of two or more thereof.

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

where X is chosen from a polyurethane; a polyester; a polyether; a polycarbonate; a polyolefin; a polyesterether; and a polyorganosiloxane having units of R 3 SiO 1/2 ,

Assignees

• Momentive Performance Mat Inc

Inventors

• Jenkins David
• Byrne Christopher Michael
• Patel Mihirkumar Maheshbhai
• Dhanabalan Anantharaman

Classifications

• C08L83/16

  in which all the silicon atoms are connected by linkages other than oxygen atoms · CPC title

• C08J2371/00

  Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers · CPC title

• C09J201/10

  containing hydrolysable silane groups · CPC title

• C08L43/04

  Homopolymers or copolymers of monomers containing silicon · CPC title

• C08G77/08

  characterised by the catalysts used · CPC title