Moisture curable organopolysiloxane compositions

Patent metadata

Field	Value
Publication number	US-9523002-B2
Application number	US-201214365275-A
Country	US
Kind code	B2
Filing date	Dec 7, 2012
Priority date	Dec 15, 2011
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

The present invention provides curable compositions comprising non-Sn organo-metal catalysts that accelerate the condensation curing of moisture curable silicones/non-silicones. In particular, the present invention provides La(III) complexes that are particularly suitable as replacements for organotin for sealant and RTV formulations. The La(III) complexes are comparable to organotin such as DBTDL and exhibit certain behavior in the presence of components that allow for tuning or adjusting the cure characteristics of the present compositions and provide good adhesion and storage stability.

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;
(C) a catalyst chosen from a lanthanum (III) (La-III) complex;
(D) at least one adhesion promoter chosen from a silane or siloxane other than the compounds listed under (B);
(E) optionally, a filler component; and
(F) at least one co-catalyst chosen from an acidic compound.

2. The composition of claim 1 , wherein the metal catalyst component (C) comprises a La(III) complex of the formula (1):
La III Y 3-c A c   (1)

wherein Y is a chelating ligand chosen from a diketonate, a diamine, a triamine, an aminoacetate, a nitriloacetate, a bipyridin, a glyoxime, or a combination of two or more thereof; and A is an anion, and c is a number between 0 to 2 or an integer.

3. The composition of claim 2 , wherein the chelating agent Y comprises a substituted or unsubstituted diketonate.

4. The composition of claim 2 , wherein the anion A is chosen from a branched C4-C19-alkyl carboxylic acid, a C4-C12-alkylsulfonate, or a combination thereof.

5. The composition of claim 1 - 4 , comprising component (C) in an amount of about 0.01 to about 7 parts per weight per 100 parts per weight of the polymer (A).

6. The composition of claim 1 , comprising component (C) in an amount of about 0.05 to about 5 parts per weight per 100 parts per weight of the polymer (A).

7. The composition of claim 1 , comprising component (C) in an amount of about 0.01 to about 1.0 parts per weight per 100 parts per weight of the polymer (A).

8. The composition of claim 1 , comprising component (C) in an amount of about 0.02 to about 0.4 parts per weight per 100 parts per weight of the polymer (A).

9. The composition of claim 1 , wherein the component (F) is chosen from a mono ester of a phosphate; a phosphonate of the formula (R 3 O)PO(OH) 2 , (R 3 O)P(OH) 2 , or R 3 P(O)(OH) 2 where R 3 is a C 1 -C 18 -alkyl, a C 2 -C 20 -alkoxyalkyl, phenyl, a C 7 -C 12 -alkylaryl, a poly(C 2 -C 4 -alkylene) oxide ester or its mixtures with diesters; a branched alkyl C 4 -C 30 -alkyl carboxylic acid; or a combination of two or more thereof.

10. The composition of claim 1 , wherein the component (F) comprises a mixture of branched alkyl C 4 -C 30 alkyl carboxylic acid comprising C 5 -C 30 acids having an alpha tertiary carbon.

11. The composition of claim 1 , comprising from about 0.01 to about 5 wt. % of the component (F).

12. The composition of claim 1 comprising the component (F) in an amount of from about 0.01 to about 8 pt. wt. per 100 pt. wt. of component (A).

13. The composition of claim 1 comprising the component (F) in an amount of from about 0.02 to about 1 pt. wt. per 100 pt. wt. of component (A).

14. 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 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 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, 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.

15. The composition of claim 1 , wherein the component (B) is 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 alkaryaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof.

16. The composition of claim 1 wherein the crosslinker 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 ) 1-2 (NHCOR) 2-1 ; (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(l-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(N-ethylpropionamido)silane; methyldimethoxy(N-methylacetamido)silane; methyltris(N-methylacetamido)silane; ethyldimethoxy(N-methylacetamido)silane; methyltris(N-methylbenzamido)silane; methylmethoxybis(N-methylacetamido)silane; methyldimethoxy(caprolactamo)silane; trimethoxy(N-methylacetamido)silane; methyldimethoxyethylacetimidatosilane; methyldimethoxypropylacetimidatosilane; methyldimethoxy(N,N′,N′-trimethylureido)silane; methyldimethoxy(N-allyl-N′,N′-dimethylureido)silane; methyldimethoxy(N-phenyl-N′,N′-dimethylureido)silane; methyldimethoxyisocyanatosilane; dimethoxydiisocyanatosilane; methyldimethoxythioisocyanatosilane; methylmethoxydithioisocyanatosilane, or a combination of two or more thereof.

17. The composition of claim 1 , wherein the adhesion promoter component (D) is chosen from an aminoalkyltrialkoxysilane, an aminoalkylalkyldialkoxysilane, a bis(alkyltrialkoxysilyl)amine, a tris(alkyltrialkoxysilyl)amine, a tris(alkyltrialkoxysilyl)cyanuarate, and a tris(alkyltrialkoxysilyl)isocyanuarate, or a combination of two or more thereof.

18. The composition of claim 1 , comprising about 1 to about 10 wt. % of the crosslinker component (B) based on 100 wt. % of the polymer component (A).

19. The composition of claim 1 , wherein the crosslinker component (B) is chosen from a silane or a siloxane, the silane or siloxane having two or more reactive groups that can undergo hydrolysis and/or condensation reaction with polymer (A) or on its own in the presence of water and component (F).

20. The composition of claim 1 , wherein the polymer component (A) is chosen from a polyorganosiloxane comprising divalent units of the formula [R 2 SiO] in the backbone, wherein R is chosen from a C 1 -C 10 -alkyl; a C 1 -C 10 alkyl substituted with one or m

Assignees

• Dinkar Sumi
• Dhanabalan Anantharaman
• Momentive Performance Mat Inc

Inventors

• Dinkar Sumi
• Dhanabalan Anantharaman

Classifications

• C08K5/09

  Carboxylic acids; Metal salts thereof; Anhydrides thereof · CPC title

• C08G77/04

  Polysiloxanes · CPC title

• C08L83/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers · CPC title

• C08G77/08

  characterised by the catalysts used · CPC title

• C08K5/00

  Use of organic ingredients · CPC title