Moisture curable organopolysiloxane compositions

Patent metadata

Field	Value
Publication number	US-9493691-B2
Application number	US-201414775065-A
Country	US
Kind code	B2
Filing date	Feb 27, 2014
Priority date	Mar 13, 2013
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

The present invention provides curable compositions that are substantially free of metal catalysts including both tin and non-tin metal catalysts. The curable compositions employ a catalyst composition comprising the combination of a (i) carbodiimide functional compound, and (ii) an amino-containing compound such as an amino silane functional compound and/or an organic amine compound. The combination of these materials, particularly when aged, accelerates the condensation curing of moisture curable silicones/non-silicones even in the absence of a metal-based catalyst.

First claim

We 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; and
(C) a catalyst composition comprising (i) a carbodiimide functional compound, and (ii) an amino silane functional compound, an organic amine, or a combination thereof wherein the catalyst composition is aged for at least one hour prior to addition to the curable composition.

2. The composition of claim 1 , wherein the carbodiimide functional compound is chosen from a monocarbodiimide, a polycarbodiimide, a silica grafted carbodiimide, a silylated carbodiimide, or a combination of two or more thereof.

3. The composition of claim 1 , wherein the carbodiimide functional compound is chosen from a compound of the formula: R 6 —(N═C═N)—R 7 wherein R 6 and R 7 are the same or different and can be chosen from a hydrogen, hydrocarbyl group, a nitrogen-containing hydrocarbyl group, an oxygen-containing hydrocarbyl group, and a silicon-containing hydrocarbyl group.

4. The composition of claim 3 , wherein R 6 and R 7 are independently a C 1 -C 12 aliphatic group, C 6 -C- 18 aromatic group, or an aromatic-aliphatic group.

5. The composition of claim 1 , wherein the amino silane functional compound (ii) is chosen from N-(2-aminoethyl)aminopropyltrimethoxysilane gamma-aminopropyltriethoxysilane, gamma-aminopropyltrimethoxysilane, bis(gamma-trimethoxysilylpropyl)amine, N-phenyl-gamma-aminopropyltrimethoxysilane, triaminofunctionaltrimethoxysilane, gamma-aminopropylmethyldimethoxysilane, gamma-aminopropylmethyldiethoxysilane, omega-bis-(aminoalkyl-diethoxysilyl)-polydimethylsiloxanes (Pn=1-7), alpha, omega-bis-(aminoalkyl-diethoxysilyl)-octa-methyltetrasiloxane, 4-amino-3,3,-dimethyl-butyl-tri-methoxysilane, and N-ethyl-3-tri-methoxy-silyl-2-methylpropanamine, 3-(diethyl-aminopropyl)-trimethoxysilane or a combination of two or more thereof.

6. The composition of claim 1 , wherein the organic amine is chosen from a compound of the formula R 8 —NR 9 R 10 , wherein R 8 , R 9 , and R 10 are the same or different and can be chosen from a hydrogen, a hydrocarbyl group, a nitrogen-containing hydrocarbyl group, an oxygen-containing hydrocarbyl group, or a combination of two or more thereof.

7. The composition of claim 6 , wherein R 8 , R 9 , and R 10 are independently chosen from a C 1 -C 12 aliphatic group, a C 6 -C 18 aromatic group, or an aromatic aliphatic group.

8. The composition of claim 1 , wherein the catalyst composition (C) comprises the carbodiimide functional compound in an amount of from about 25 weight percent to about 90 weight percent, and the amino silane functional compound and/or the organic amine in an amount of from about 75 weight percent to about 10 weight percent.

9. The composition of claim 1 , wherein the catalyst composition (C) comprises the carbodiimide functional compound in an amount of from about 60 weight percent to about 75 weight percent, and the amino silane functional compound and/or the organic amine in an amount of from about 25 weight percent to about 40 weight percent.

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

11. The composition of claim 1 comprising from about 0.1 to about wt. % of the carbodiimide functional compound (C)(i) per 100 wt. % of component (A).

12. The composition of claim 1 comprising from about 0.1 to about 5 wt. % of the amino silane functional compound and/or the organic amine (C)(ii) per 100 wt. % of component (A).

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

14. The composition of claim 1 , wherein the catalyst composition (C) is aged for at least two hours prior to addition to the curable composition.

15. The composition of claim 1 , wherein the catalyst composition (C) is aged for at least three hours prior to addition to the curable composition.

16. The composition of claim 1 , wherein the catalyst composition (C) is aged for at least seven hours prior to addition to the curable composition.

17. The composition of claim 1 , wherein the catalyst composition (C) is aged for at least 24 hours prior to addition to the curable composition.

18. The composition of claim 1 , wherein the catalyst composition (C) is aged for at least 1 to 48 hours prior to addition to the curable composition.

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

20. The 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 1 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, 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.

21. 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 )(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(

Assignees

• Momentive Performance Mat Inc

Inventors

• Patel Mihirkumar
• Dhanabalan Anantharaman
• Dinkar Sumi
• Karambelkar Vivek

Classifications

• C08G77/08

  characterised by the catalysts used · CPC title

• C08L43/04

  Homopolymers or copolymers of monomers containing silicon · CPC title

• C08L2312/08

  by silane · CPC title

• C08K5/544 Primary

  containing nitrogen · CPC title

• C08G77/455

  containing polyamide, polyesteramide or polyimide sequences · CPC title