Moisture curable compositions

Patent metadata

Field	Value
Publication number	US-2016200875-A1
Application number	US-201414913769-A
Country	US
Kind code	A1
Filing date	Aug 18, 2014
Priority date	Aug 23, 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 guanidine-containing compounds that are particularly suitable as replacements for organotin in sealant and RTV formulations. Further, the compositions employing a guanidine-containing compound is comparable or superior to organotin such as DBTDL, exhibits certain behavior in the presence of components that allow for tuning or adjusting the cure characteristics of the compositions, 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; and (C) a condensation accelerator comprising a guanidine-containing compound, wherein the guanidine-containing compound comprises a plurality of guanidine functional groups.

2 . The composition of claim 1 , wherein the guanidine-containing compound comprises two guanidine functional groups.

3 . The composition of claim 1 , wherein the guanidine-containing compound comprises three guanidine functional groups.

4 . The composition of claim 1 , wherein the guanidine-containing compound comprises four guanidine functional groups.

5 . The composition of claim 1 , wherein the guanidine-containing compound is of the formula:

where R 9 , R 10 , R 11 , and R 12 are independently chosen from an alkyl, a substituted alkyl, an alkenyl, a substituted alkenyl, an alkynyl, a substituted alkynyl, a carbocycle, a heterocycle, an aryl, or a heteroaryl; and R 13 is chosen from an alkylene, a cycloalkylene, an alkynylene, an alkenylene, an arylene, a siloxane derivative, or a polysiloxane derivative.

6 . The composition of claim 5 , wherein R 9 -R 12 are individually chosen from branched or straight chain C 1 -C 30 alkyl radical, and R 13 is chosen from a C 1 -C 30 alkylene.

7 . The composition of claim 1 , wherein the guanidine-containing compound is of the formula:

8 . The composition of claim 5 , wherein R 9 -R 12 are independently chosen from a branched or straight chain C 1 -C 30 alkyl radical, and R 13 is chosen from an alkylene comprising a carbocycle.

9 . The composition of claim 8 , wherein the carbocycle comprises a bridging group, a fused ring, or a fused ring system with at least one ring in the fused ring system comprising a bridging group.

10 . The composition of claim 1 , wherein the guanidine-containing group is of the formula:

11 . The composition of claim 5 , wherein R 13 is a siloxane derivative of the formula:

where R 21 , R 22 , and R 23 can be identical or different at the same silicon atom and chosen from C 1 -C 10 alkyl; C 1 -C 10 alkyl substituted with one or more of Cl, F, N, O, or S; a phenyl; C 7 -C 16 alkylaryl; C 7 -C 16 arylalkyl; C 2 -C 20 -polyalkylene ether; or a combination of two or more thereof; R 22 and R 23 can further be chosen from OH, C 1 -C 8 alkoxy, C 2 -C 18 alkoxyalkyl, alkoxyaryl, oximoalkyl, oximoaryl, enoxyalkyl, enoxyaryl, aminoalkyl, aminoaryl, carboxyalkyl, carboxyaryl, amidoalkyl, amidoaryl, carbamatoalkyl, carbamatoaryl, or a combination of two or more thereof; L is independently chosen from a bond, a divalent unit selected from the group of a C 1 -C 14 alkylene, or O; and k is 0 to 1000.

12 . The composition of claim 1 , wherein the guanidine-containing group is of the formula:

13 . The composition of claim 1 , wherein the guanidine-containing compound is of the formula:

where R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are independently chosen from hydrogen, an alkyl, a substituted alkyl, an alkenyl, a substituted alkenyl, an alkynyl, a substituted alkynyl, a carbocycle, a heterocycle, an aryl, or a heteroaryl; and R 20 is chosen from an alkylene, a cycloalkylene, an alkynylene, an alkenylene, an arylene, a siloxane derivative, or a polysiloxane derivative.

14 . The composition of claim 1 comprising from about 0.0001 to about 10 parts per weight of accelerator (C) per 100 parts per weight of the polymer (A).

15 . The composition of claim 1 comprising from about 0.005 to about 0.05 wt. pt. of accelerator (C) per 100 parts of component.

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

17 . 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.

18 . 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 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 and 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; and Z is a bond, a divalent unit selected from the group of a C 1 -C 8 alkylene, or O.

19 . The polymer composition of claim 1 , wherein the polymer component (A) has the formula (4):
R 2 3-a R 1 a Si—Z—[R 2 SiO] x [R 1 2 SiO] y —Z—SiR 1 a R 2 3-a   (4)

where x is 0 to 10000; y is 0 to 1000; a is 0 to 2; R is methyl; R 1 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 enoxyalkyl, an enoxyaryl, an aminoalkyl, an aminoaryl, a carboxyalkyl, a carboxyaryl, an amidoalkyl, an amidoaryl, a carbamatoalkyl, a carbamatoaryl, or a combination of two or more thereof; and Z is —O—, a bond, or —C 2 H 4 —.

20 . The composition of claim 1 , wherein the polymer (A) is chosen from silylated polyurethane (SPUR), silylated polyester, silylated polyether, silylated polycarbonate, silylated polyolefins like polyethylene, polypropylene, silylated polyesterether and combinations of two or more thereof.

21 . The composition of claim 1 , wherein the crosslinker (B) is chosen from an alkoxysilane, an alkoxysiloxane, an oximosilane, an oximosiloxane, an enoxysilane, an enoxysiloxane, an aminosilane, an aminosiloxane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alklarylaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, a hydridosilane, a hydridosiloxane, and combinations of two or more thereof.

22 . The composition of claim 1 wherein the crosslinker component (B) is chosen from tetraethylorthosilicate (TEOS)

Assignees

• Momentive Performance Mat Inc

Inventors

• Patel Mihirkumar Maheshbhai
• Dhanabalan Anantharaman

Classifications

• C08L101/10

  containing hydrolysable silane groups · CPC title

• C07C277/00

  Preparation of guanidine or its derivatives, i.e. compounds containing the group [IMAGE cpc-sch-C07C-0970.gif], the singly-bound nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C07C2603/68

  Dicyclopentadienes; Hydrogenated dicyclopentadienes · CPC title

• C08G77/442 Primary

  containing vinyl polymer sequences · CPC title

• C07F7/0838

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title