Process for preparing tris[3-(alkoxysilyl)propyl]isocyanurates

Patent metadata

Field	Value
Publication number	US-10125156-B2
Application number	US-201815915126-A
Country	US
Kind code	B2
Filing date	Mar 8, 2018
Priority date	Mar 8, 2017
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

The present invention relates to a process for preparing a tris[3-(alkoxysilyl)propyl] isocyanurate from the group of tris[3-(trialkoxysilyl)propyl] isocyanurate, tris[3-(alkyldialkoxysilyl)propyl] isocyanurate and tris[3-(dialkylalkoxysilyl)propyl] isocyanurate by hydrosilylation,
by

in step A initially charging a mixture comprising 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione as olefin component, at least one carboxylic acid and a Pt catalyst, heating the mixture to a temperature of 50 to 140° C.,
in step B adding at least one hydroalkoxysilane from the group of hydrotrialkoxysilane, hydroalkyldialkoxysilane, hydrodialkylalkoxysilane [called H-silane(s) for short] to the mixture from step A while mixing,
in step C leaving the mixture from step B to react while mixing, with addition of at least a defined amount of alcohol to the mixture as further cocatalyst, and
in step D working up the product mixture thus obtained.

First claim

The invention claimed is:

1. A process for preparing a tris[3-(alkoxysilyl)propyl]isocyanurate of the formula:

comprising the following steps:
(A) preparing a mixture comprising at least one carboxylic acid, a platinum catalyst and 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione of the formula:

(B) heating the mixture prepared in step (A) to a temperature in the range of 40° C.-140° C.;
(C) adding a hydrosilane of the formula:
(CH 3 O) 3 SiH,

to the mixture prepared in step (B);
(D) adding at least one alcohol to the mixture prepared in step (C); and
(E) isolating the tris[3-(alkoxysilyl)propyl]isocyanurate of the formula above.

2. The process according to claim 1 , wherein the molar ratio of the hydrosilane to the at least one alcohol is 1:0.005-0.3.

3. The process according to claim 1 , wherein the molar ratio of the hydrosilane to the platinum catalyst is 1:0.000000001-0.0001.

4. The process according to claim 1 , wherein the molar ratio of the hydrosilane to the at least one carboxylic acid is 1:0.001-0.03.

5. The process according to claim 1 , wherein the molar ratio of the hydrosilane to 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione is 1:0.1-1.

6. The process according to claim 1 , wherein the at least one carboxylic acid is selected from the group consisting of benzoic acid, propionic acid, 2,2-dimethylpropionic acid, 3,5-di-tert-butylbenzoic acid, 3,5-di-tert-butyl-4-hydroxybenzoic acid and acetic acid.

7. The process according to claim 1 , wherein the at least one alcohol is selected from the group consisting of methanol, ethanol, tert-butanol, benzyl alcohol and diglycol monomethyl ether.

8. The process according to claim 1 , wherein the at least one alcohol is a C 1 -C 10 alcohol.

9. The process according to claim 1 , wherein the at least one alcohol is tert-butanol.

10. The process according to claim 1 , wherein the platinum catalyst is selected from the group consisting of a Karstedt catalyst, a hexachloroplatinum(IV) acid and platinum adsorbed on a solid support.

11. The process according to claim 1 , wherein the platinum catalyst is selected from the group consisting of a platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in the form of a Karstedt catalyst in xylene or toluene with a 0.5%-5% w/w platinum(0) content, hexachloroplatinum(IV) acid dissolved in acetone and platinum adsorbed on activated carbon.

12. The process according to claim 1 , wherein the platinum catalyst is a platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in the form of a Karstedt catalyst in xylene or toluene with a 0.5%-5% w/w platinum(0) content.

13. The process according to claim 1 , wherein the process further comprises performing step (C) at a temperature in the range of 91° C.-111° C.

14. The process according to claim 1 , wherein the process further comprises performing step (D) at a temperature in the range of 96° C.-111° C.

15. The process according to claim 1 , wherein the process further comprises recovering the platinum catalyst from the mixture formed in step (D) prior to performing step (E).

16. The process according to claim 1 , wherein the process further comprises performing step (E) via distillation at a temperature in the range of 45° C.-150° C. and at a pressure less than 1 bar.

Assignees

• Evonik Degussa Gmbh

Inventors

• Albert Philipp
• Just Eckhard

Classifications

• C07F7/1836

  Chemistry & Metallurgy · mapped topic

• C07F7/1876 Primary

  by reactions involving the formation of Si-C linkages · CPC title

• C07F7/1804 Primary

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

• B01J27/13

  Platinum group metals · CPC title

• B01J21/18

  Carbon · CPC title