Compositions comprising alkoxysilane-containing isocyanates and acid stabilisers

Patent metadata

Field	Value
Publication number	US-9593135-B2
Application number	US-201314433186-A
Country	US
Kind code	B2
Filing date	Sep 25, 2013
Priority date	Oct 23, 2012
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

The present invention relates to a composition comprising (A) an isocyanate of formula (I) OCN-A-SiR 1 R 2 R 3 (I), wherein A is straight-chain, branched, substituted and/or unsubstituted aliphatic hydrocarbyl of 1 to 12 carbon atoms or substituted or unsubstituted cycloaliphatic hydrocarbyl of 4 to 18 carbon atoms, wherein R 1 is selected from the group comprising —O—R alk , wherein R 2 and R 3 are each independently selected from the group of substituents comprising —R alk and —O—R alk , and wherein —R alk is hydrocarbyl of 1 to 6 carbon atoms, and B) a Bronstedt or Lewis acid or a compound which releases a Bronstedt or Lewis acid at room temperature; and also to a process for producing a stabilized alkoxysilane-containing isocyanate comprising the step of adding a Lewis or Bronstedt acid or a compound which releases a Bronstedt or Lewis acid at room temperature to an alkoxysilane-containing isocyanate.

First claim

The invention claimed is:

1. A composition comprising
A) an isocyanate of formula (I)
OCN-A-SiR 1 R 2 R 3   (I),

wherein A is a straight-chain, branched, substituted and/or unsubstituted aliphatic hydrocarbyl of 1 to 12 carbon atoms or substituted or unsubstituted cycloaliphatic hydrocarbyl of 4 to 18 carbon atoms,
wherein R 1 has a formula —O—R alk ,
wherein R 2 and R 3 are each independently selected from the group of substituents consisting of —R alk and —O—R alk , and
wherein —R alk is a hydrocarbyl of 1 to 6 carbon atoms, and
B) a Bronstedt or Lewis acid or a compound which releases a Bronstedt or Lewis acid at room temperature selected from the group consisting of a carboxylic acid, a mineral acid, an acyl halide, an alkyl halide, an aryl halide and a mixture thereof
wherein the Bronstedt or Lewis acid or the compound which releases a Bronstedt or Lewis acid at room temperature is present in an amount of 0.0001 to 1 per cent by weight of the mass of the isocyanate in the composition.

2. The composition according to claim 1 , wherein the Bronstedt or Lewis acid or the compound which releases a Bronstedt or Lewis acid at room temperature is an aryl halide a compound of formula (II)

wherein R 5 is selected from the group consisting of halogen, —CO-halogen and —CH 2 -halogen, and R 6 is selected from the group consisting of hydrogen, —CH 2 -halogen, halogen and —CO-halogen.

3. The composition according to claim 1 , wherein the isocyanate has a formula OCN—(CH 2 ) n —Si(OR 7 ) 3 wherein n is 1 to 12 and R 7 is either methyl or ethyl.

4. The composition according to claim 1 , further comprising
C) a compound having one or more NCO-reactive hydroxyl, thiol, —NH—, carbon-acid and/or amine groups.

5. The composition according to claim 4 , wherein a stoichiometric ratio between a totality of NCO-reactive hydroxyl, thiol, NH, carbon-acid and/or amine groups of C) to a totality of NCO groups of A) is 2:1 to 1:2.

6. A process for preparing a polymer, comprising curing the composition according to claim 4 .

7. A process for preparing a stabilized alkoxysilane-containing isocyanate, comprising
e) adding a Lewis or Bronstedt acid or a compound which releases a Bronstedt or Lewis acid at room temperature to an alkoxysilane-containing isocyanate,
wherein the Bronstedt or Lewis acid or the compound which releases a Bronstedt or Lewis acid at room temperature is present in an amount of 0.0001 to 1 per cent by weight of the sum of the acid and isocyanate.

8. A process for preparing a stabilized alkoxysilane-containing isocyanate, comprising
a1) reacting an alkoxysilanealkylamine of formula (III)
H 2 N-A-SiR 1 R 2 R 3   (III)

with urea to form a (cyclo) alkylenebisurea of formula (IV)
H 2 N—OC—NH-A-SiR 1 R 2 R 3   (IV),

b1) reacting the (cyclo)alkylenebisurea of formula (IV) from a) with an alcohol of formula R 8 —OH to form a carbamate of formula (V)
R 8 O—OC—NH-A-SiR 1 R 2 R 3   (V)

or
a2) reacting an alkoxysilanealkylamine of formula (III)
H 2 N-A-SiR 1 R 2 R 3   (III)

with urea in the presence of an alcohol of formula R 8 —OH to form a carbamate of formula (V)
R 8 O—OC—NH-A-SiR 1 R 2 R 3   (V),

and also additionally to the combination of a1) and b1) or additionally to a2)
c) removing the alcohol of formula R 8 —OH after b1) or a2) to form a reaction mixture separated from the alcohol, and
d) thermally cracking the reaction mixture separated from the alcohol, at a temperature of 180 to 280° C. at a pressure of 0.1 to 200 mbar,
wherein A is a straight-chain, branched, substituted and/or unsubstituted aliphatic hydrocarbyl of 1 to 12 carbon atoms or substituted or unsubstituted cycloaliphatic hydrocarbyl of 4 to 18 carbon atoms,
wherein R 1 has a formula —O—R alk ,
wherein R 2 and R 3 are each independently selected from the group of substituents consisting of —R alk , and —O—R alk ,
wherein —R alk is hydrocarbyl of 1 to 6 carbon atoms, and
wherein R 8 is a substituted or unsubstituted alkyl, cycloalkyl, aryl or aralkyl; and
e) adding a Lewis or Bronstedt acid or a compound which releases a Bronstedt or Lewis acid at room temperature to an alkoxysilane-containing isocyanate.

9. The process according to claim 7 , wherein the Bronstedt or Lewis acid or the compound which releases a Bronstedt or Lewis acid at room temperature is selected from the group consisting of a carboxylic acid, a mineral acid, an acyl halide, an alkyl halide, and an aryl halide.

10. The process according to claim 7 , wherein the isocyanate has a formula OCN—(CH 2 ) n —Si(OMe) 3 wherein n is from 1 to 12.

11. The process according to claim 8 , wherein b1) or a) are carried out in a pressure distillation reactor with removal of resultant ammonia.

12. A composition consisting essentially of
A) an isocyanate of formula (I)
OCN-A-SiR 1 R 2 R 3   (I),

wherein A is a straight-chain, branched, substituted and/or unsubstituted aliphatic hydrocarbyl of 1 in 12 carbon atoms or substituted or unsubstituted cycloaliphatic hydrocarbyl of 4 to 18 carbon atoms,
wherein R 1 has a formula —O—R alk ,
wherein R 2 and R 3 are each independently selected from the group of substituents consisting of —R alk and —O—R alk , and
wherein —R alk is a hydrocarbyl of 1 to 6 carbon atoms, and
B) a Bronstedt or Lewis acid or a compound which releases a Bronstedt or Lewis acid at room temperature which is selected from the group consisting of a carboxylic acid, a mineral acid, an acyl halide, an alkyl halide, an aryl halide and a mixture thereof.

Assignees

• Spyrou Emmanouil
• Kreczinski Manfred
• Loesch Holger
• Thesing Andrea
• Hellkuhl Lars
• Evonik Degussa Gmbh

Inventors

• Spyrou Emmanouil
• Kreczinski Manfred
• Loesch Holger
• Thesing Andrea
• Hellkuhl Lars

Classifications

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07F7/1892

  by reactions not provided for in C07F7/1876 - C07F7/1888 · CPC title

• C08G18/718

  containing silicon · CPC title

• C08G18/34

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• C08G18/3876

  containing mercapto groups · CPC title