Moisture curable composition with amino acids

Patent metadata

Field	Value
Publication number	US-9914809-B2
Application number	US-201414914887-A
Country	US
Kind code	B2
Filing date	Aug 29, 2014
Priority date	Aug 30, 2013
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

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

What is claimed is:

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, chosen from 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 is an acetyl; 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.

2. The composition of claim 1 , wherein R 9 is a group other than hydrogen.

3. The composition of claim 1 , wherein R 13 is chosen from a functional group of the formula:

4. The composition of claim 3 , wherein X is O, and R 14 is a C 1 -C 6 alkyl group.

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

6. 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.

7. 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.

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

9. 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).

10. 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.

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

12. 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.

13. The polymer 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 , R 2 SiO, RSiO 3/2 , and/or SiO 2 ;
n is 0 to 100; a is 0 to 2; R′ 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, C 1 -C 8 alkoxy, C 2 -C 18 alkoxyalkyl, oximoalkyl, enoxyalkyl, aminoalkyl, carboxyalkyl, amidoalkyl, amidoaryl, 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.

14. The polymer composition of claim 1 wherein the polymer component (A) has the formula (2):
R 2 3-c R 1 c Si—Z—[R 2 SiO] x [R 1 2 SiO] y —Z—SiR 1 c R 2 3-c   (2)

where 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, C 1 -C 8 alkoxy, C 2 -C 18 alkoxyalkyl, oximoalkyl, enoxyalkyl, aminoalkyl, carboxyalkyl, amidoalkyl, amidoaryl, carbamatoalkyl, or a combination of two or more thereof, Z is a bond, a divalent unit selected from the group of a C 1 -C 8 alkylene, or O; R is C 1 -C 6 alkyl (an exemplary alkyl being methyl); x is 0 to about 10,000.

15. The polymer composition of claim 1 wherein the polymer component (A) has the formula (3):
R 2 3-c-d SiR 3 c R 4 d —[OSiR 3 R 4 ] x —[OSiR 3 R 4 ] y —OSiR 3 e R 4 f R 2 3-e-f   (3)

where x is 0 to 10000; y is 0 to 1000; c, d, and f are independently chosen from 0 to 2; R′ is 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, and other siloxane units may be present in amounts less than 10 mol. % preferably methyl, vinyl, phenyl; R 2 is chosen from OH, a C 1 -C 8 alkoxy, a C 2 -C 18 alkoxyalkyl, an oximoalkyl, an oximoaryl, an eno

Assignees

• Momentive Performance Mat Inc

Inventors

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

Classifications

• C08K5/54

  Silicon-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C08K5/175 Primary

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

• C08L83/16

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

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C08L83/04

  Polysiloxanes · CPC title