# US 2018/0022762 A1 · Process for preparing tris[3-(alkoxysilyl)propyl] isocyanurates

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- Number: US 2018/0022762 A1
- Document ID: US20180022762A1
- Status: Published application
- Kind: A1
- Application number: 15/658,074
- Filed: 2017-07-24
- Published: 2018-01-25
- Earliest claimed: 2016-07-22
- Assignees: Evonik Degussa GmbH
- Applicants: Evonik Degussa GmbH
- Inventors: Philipp ALBERT; Eckhard JUST
- Web page: https://patentgrep.com/patent/US20180022762A1

## CPC

- C07F 7/1876: {by reactions involving the formation of Si-C linkages}
- C07D 251/34: Cyanuric or isocyanuric esters
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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.

## Claims

### Claim 1

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,
said process comprising:
a) initially charging a mixture of at least one hydroalkoxysilane from the group of hydrotrialkoxysilane, hydroalkyldialkoxysilane, hydrodialkylalkoxysilane [H-silane(s)] 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,
d) leaving the mixture to react and then working up the product mixture thus obtained.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

The process according to claim 1, wherein H-silane is used relative to Pt in a molar ratio of 1:1×104 to 1×10−9.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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, acetic acid.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the alcohol is selected from the group consisting of the C1-C10 alcohols.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the H-silane used is hydrotrimethoxysilane (TMOS), hydrotriethoxysilane (TEOS), methyldiethoxysilane (DEMS), methyldimethoxysilane (DMMS), dimethylethoxysilane (DMES) or dimethylmethoxysilane (MDMS).

### Claim 9 (depends on 1)

The process according to claim 1, wherein a Pt catalyst from the “Karstedt catalyst” group is used, or Pt applied to a solid catalyst support.

### Claim 10 (depends on 1)

The process according to claim 1, wherein
a) the H-silane and Pt catalyst components are initially charged and heated as a mixture,
b) olefin component, carboxylic acid and alcohol are combined and the mixture comprising olefin component [1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione], carboxylic acid and 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,
c) the mixture is subsequently left to react over a period of time of 0.5 to 2 hours; optionally—if a heterogeneous catalyst is used—removing it from the product mixture thus obtained, and
d) the subsequent distillative workup of the product mixture obtained is performed at 45-150° C. and a reduced pressure, by removing low boilers that are present from the product mixture to obtain the tris[3-(alkoxysilyl)propyl] isocyanurate.