Moisture curable organopolysiloxane composition

Patent metadata

Field	Value
Publication number	US-9394443-B2
Application number	US-201214357346-A
Country	US
Kind code	B2
Filing date	Nov 9, 2012
Priority date	Nov 10, 2011
Publication date	Jul 19, 2016
Grant date	Jul 19, 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 Fe(III) and Bi(III) complexes that are particularly suitable as replacements for organotin for sealant and RTV formulations. The Fe(III) and Bi(III) complexes are comparable or superior 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 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;
(C) about 0.01-7 parts per weight per 100 parts per weight of the polymer (A) of a catalyst selected from a Fe(III) complex of the Formula (1), a Bi(III) complex of the Formula (2), or a combination thereof:
Fe III Y 3-c A c   (1)

Bi III Y 3-c A c   (2)

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 chosen from substituted, unsubstituted alkyl- and aryl carboxylates, and c is a number between 0 to 3 or an integer;
(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 acidic compound chosen from a phosphate ester, a phosphonate, a phosphite, a phosphine, a sulfite, a pseudohalogenide, a branched alkyl carboxylic acid, and a combination of two or more thereof.

2. The composition of claim 1 , wherein the chelating agent Y comprises a substituted diketonate, the carboxylate anion A is chosen from pentanoate, hexanoate, heptanoate, octoate, neodecanoate, 2-ethylhexanoate, or a combination of two or more thereof.

3. The composition of claim 1 , wherein catalyst (C) comprises a complex Fe III Y 3-c A c whereby c=0 and Y is 3-methyl-2,4-pentadionate.

4. The composition of claim 1 , wherein catalyst (C) comprises a complex Bi III Y 3-c A c and whereby c=3 and the anion A is a branched C 4 -C 19 alkyl carboxylate.

5. The composition of claim 1 comprising the catalyst (C) in an amount of about 0.1 to about 2 parts per weight per 100 parts per weight of the polymer (A).

6. The composition of claim 1 comprising the catalyst (C) in an amount of about 0.2 to about 0.7 parts per weight per 100 parts per weight of the polymer (A).

7. The composition of claim 1 , wherein the acidic component (F) is added in a molar ratio of (F):(C) of 1:10 to 1:4.

8. 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 14 -alkyl carboxylic acid; or a combination of two or more thereof.

9. 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
is a bond, a divalent unit selected from the group of a C 1 -C 8 alkylene, or O.

10. 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(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(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.

11. 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.

12. The composition of claim 1 comprising about 0.1 to about 5 pt. wt. of the adhesion promoter (D) per 100 parts per weight of the polymer (A).

13. 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.

14. The composition of claim 1 wherein the adhesion promoter comprises an aminoalkyltrialkoxysilane and a bis(alkyltrialkoxysilyl)amine.

15. The composition of claim 1 , wherein the adhesion promoter comprises bis(3-propyltrimethoxysilyl)amine and 3-aminopropyltrimethoxy silane.

16. 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)

whereby
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

Assignees

• Dinkar Sumi
• Maheshbai Mihirkumar Patel
• Dhanabalan Anantharaman
• Momentive Performance Mat Inc

Inventors

• Dinkar Sumi
• Maheshbai Mihirkumar Patel
• Dhanabalan Anantharaman

Classifications

• B01J2531/54

  Bismuth · CPC title

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• B01J2231/14

  Other (co) polymerisation, e.g. of lactides or epoxides · CPC title

• C09D183/04

  Polysiloxanes · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title