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

Patent metadata

Field	Value
Publication number	US-9951091-B2
Application number	US-201715658074-A
Country	US
Kind code	B2
Filing date	Jul 24, 2017
Priority date	Jul 22, 2016
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

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 is prepared by hydrosilylation, by a) initially charging a mixture of at least one hydroalkoxysilane from the group of hydrotrialkoxysilane, hydroalkyldialkoxysilane, hydrodialkylalkoxysilane [called H-silane(s) for short] and a Pt catalyst, b) heating the mixture to a temperature of 40 to 170° C., c) then adding or metering in 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, at least one carboxylic acid and at least one alcohol as cocatalyst while mixing, and d) leaving the mixture to react and then working up the product mixture thus obtained.

First claim

The invention claimed is:

1. A process for preparing at least one tris[3-(alkoxysilyl)propyl] isocyanurate selected from the group consisting of tris[3-(trialkoxysilyl)propyl] isocyanurate, tris[3-(alkyldialkoxysilyl)propyl] isocyanurate and tris[3-(dialkylalkoxysilyl)propyl] isocyanurate by hydrosilylation,
the process comprising:
a) preparing a mixture of at least one hydroalkoxysilane (H-silane) selected from the group consisting of hydrotrialkoxysilane, hydroalkyldialkoxysilane, and hydrodialkylalkoxysilane, and a Pt catalyst;
b) heating the mixture to a temperature of 40 to 170° C.;
c) then adding or metering in an olefin component which is 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, at least one carboxylic acid and at least one alcohol as cocatalyst to the mixture while mixing the mixture; and
d) leaving the mixture to react with the olefin component, the carboxylic acid, and the alcohol to produce a product mixture comprising the tris[3-(alkoxysilyl)propyl] isocyanurate.

2. The process according to claim 1 , wherein a molar ratio of the H-silane to the alcohol is 1:0.01 to 0.2.

3. The process according to claim 1 , wherein a molar ratio of the H-silane to the Pt catalyst is 1:1×10 −4 to 1×10 −9 .

4. The process according to claim 1 , wherein a molar ratio of the H-silane to the carboxylic acid is 1:1×10 −3 to 30×10 −3 .

5. The process according to claim 1 , wherein a molar ratio of the H-silane to the olefin component is 1:0.1 to 0.5.

6. The process according to claim 1 , wherein the carboxylic acid is at least one selected from the group consisting of benzoic acid, propionic 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 alcohol is a C1-C10 alcohol.

8. The process according to claim 1 , wherein the H-silane is at least one selected from the group consisting of hydrotrimethoxysilane (TMOS), hydrotriethoxysilane (TEOS), methyldiethoxysilane (DEMS), methyldimethoxysilane (DMMS), dimethylethoxysilane (DMES), and dimethylmethoxysilane (MDMS).

9. The process according to claim 1 , wherein the Pt catalyst is a Karstedt catalyst or is Pt applied to a solid catalyst support.

10. The process according to claim 1 , further comprising:
after the leaving in d), removing a heterogeneous catalyst, if any, from the product mixture; and then
performing a distillative workup at 45-150° C. and a reduced pressure, to remove low boilers from the product mixture to obtain the tris[3-(alkoxysilyl)propyl] isocyanurate,
wherein
the H-silane and the Pt catalyst are initially charged and heated as a mixture,
the olefin component, the carboxylic acid and the alcohol are combined and a cocatalyst mixture comprising the olefin component, the carboxylic acid and the alcohol is metered into the initial charge at a temperature in the initial charge of 40-135° C. while mixing over a period of time of 1 to 10 hours, and
in the leaving in d), the mixture is left to react over a period of time of 0.5 to 2 hours.

11. The process according to claim 1 ,
wherein a molar ratio of the H-silane to the alcohol is 1:0.01 to 0.2,
a molar ratio of the H-silane to the Pt catalyst is 1:1×10 −4 to 1×10 −9 ,
a molar ratio of the H-silane to the carboxylic acid is 1:1×10 −3 to 30×10 −3 , and
a molar ratio of the H-silane to the olefin component is 1:0.1 to 0.5.

12. The process according to claim 1 ,
wherein a molar ratio of the H-silane to the alcohol is 1:0.02 to 0.2,
a molar ratio of the H-silane to the Pt catalyst is 1:1×10 −4 to 9×10 −6 ,
a molar ratio of the H-silane to the carboxylic acid is 2.7×10 −3 to 6×10 −3 , and
a molar ratio of the H-silane to the olefin component is 1:0.25 to 0.33.

13. The process according to claim 12 ,
wherein the carboxylic acid is at least one selected from the group consisting of benzoic acid, propionic acid, 3,5-di-tert-butylbenzoic acid, 3,5-di-tert-butyl-4-hydroxybenzoic acid, and acetic acid,
the H-silane is at least one selected from the group consisting of hydrotrimethoxysilane (TMOS), hydrotriethoxysilane (TEOS), methyldiethoxysilane (DEMS), methyldimethoxysilane (DMMS), dimethylethoxysilane (DMES), and dimethylmethoxysilane (MDMS), and
the alcohol is at least one selected from the group consisting of tert-butanol, methanol, ethanol, benzyl alcohol, and diethylene glycol monomethyl ether.

14. The process according to claim 1 , wherein the product mixture comprises 97.5 mol % or more of the tris[3-(alkoxysilyl)propyl] isocyanurate with respect to all compounds produced by hydrosilylation of the olefin component.

Assignees

• Evonik Degussa Gmbh

Inventors

• Albert Philipp
• Just Eckhard

Classifications

• C07F7/1804

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

• C07D251/34

  Cyanuric or isocyanuric esters · CPC title

• C07F7/1876 Primary

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

• B01J2531/828

  Platinum · CPC title

• B01J31/1616

  Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts (catalysts comprising molecular sieves B01J29/00) · CPC title