Process for producing hydrosilylable polyoxyalkylene ethers

Patent metadata

Field	Value
Publication number	US-10301427-B2
Application number	US-201815863156-A
Country	US
Kind code	B2
Filing date	Jan 5, 2018
Priority date	Feb 10, 2017
Publication date	May 28, 2019
Grant date	May 28, 2019

Abstract

Described are a process for producing hydrosilylable polyoxyalkylene ethers, comprising the steps of (1) alkoxylation of at least one terminally unsaturated alcohol with alkylene oxides to afford a polyoxyalkylene ether, (2) etherification of the polyoxyalkylene ether from step (1) and (3) neutralization of the product from step (2) under buffered conditions, and hydrosilylable polyoxyalkylene ether mixtures.

First claim

The invention claimed is:

1. A process for producing hydrosilylable polyoxyalkylene ethers, comprising the steps of
(1) alkoxylation of at least one terminally unsaturated alcohol with alkylene oxides to afford a polyoxyalkylene ether,
(2) etherification of the polyoxyalkylene ether from step (1) and
(3) neutralization of the product from step (2) under buffered conditions.

2. The process according to claim 1 , wherein in step (3) the product from step (2) is admixed with a buffer solution before the acid addition.

3. The process according to claim 1 , wherein step (3) is performed in the presence of water.

4. The process according to claim 1 , wherein the buffer solution has a buffering range between pH 3.5 and 9.0.

5. The process according to claim 1 , wherein the buffer solution comprises phosphate as the buffer substance.

6. The process according to claim 1 for producing mixtures of hydrosilylable polyoxyalkylene ethers comprising hydrosilylable propylene-containing polyoxyalkylene ethers.

7. The process according to claim 1 for producing hydrosilylable polyoxyalkylene ether mixtures comprising compounds of general formulae (1a) and (1b),

where
R1 is independently at each occurrence a hydrogen radical or an alkyl group having 1 to 8 carbon atoms,
R2 is independently at each occurrence a hydrogen radical, an alkyl group having 1 to 20 carbon atoms, an aryl or alkaryl group, or
R1 and one of the R2 radicals may together form a ring which includes the atoms to which R1 and R2 are bonded;
R3 is independently at each occurrence a saturated or unsaturated, aliphatic or aromatic, hydrocarbon radical having 2 to 30 carbon atoms, which is optionally further substituted,
R4 is independently at each occurrence a hydrogen radical, an alkyl group having 1 to 8 carbon atoms, which may optionally be branched, and/or an unsaturated aliphatic group, preferably <10% hydrogen radical, reported % based on the entirety of all relevant molecules containing the R4 radical,
R5 is hydrogen or methyl group,
wherein
a is from 1 to 1000,
b is from 0 to 1000, preferably 1 to 500,
with the proviso that the sum of a+b must be not less than 3 and
with the proviso that the groups having the indices a+b are freely permutable over the molecular chain,
and wherein the different monomer units of the fragments with the indices a and b may be in a blockwise structure with one another, wherein individual blocks may also occur multiple times and may be randomly distributed among one another or else are subject to a random distribution and further are freely permutable with one another in the sense that they may be arranged in any desired sequence.

8. The process according to claim 1 , wherein the buffer solution comprises hydrogenphosphate and/or dihydrogenphosphate.

9. The process according to claim 4 , wherein the buffer solution comprises hydrogenphosphate and/or dihydrogenphosphate.

10. The process according to claim 7 wherein
R1 is independently at each occurrence selected from the group consisting of hydrogen, methyl or ethyl,
R2 is independently at each occurrence selected from the group consisting of hydrogen, methyl, ethyl, octyl, decyl, dodecyl, phenyl, benzyl, or
R1 and one of the R2 radicals may together form a ring which includes the atoms to which R1 and R2 are bonded, wherein the ring comprises 5 to 8 carbon atoms,
R3 is independently at each occurrence a saturated or unsaturated, aliphatic or aromatic, hydrocarbon radical having 2 to 24 carbon atoms, and
R4 is independently at each occurrence less than 10% hydrogen radical reported % based on the entirety of all relevant molecules containing the R4 radical, an alkyl group having 1 to 8 carbon atoms.

11. The process according to claim 7 wherein
R1 is hydrogen and
R2 is selected from the group consisting of hydrogen, methyl and ethyl.

12. The process according to claim 7 wherein
a is from 3 to 100, and
b is from 1 to 500.

13. The process according to claim 7 wherein
a is from 3 to 500, and
b is from 1 to 200.

14. The process according to claim 7 wherein
a is from 4 to 50, and
b is 0.

Assignees

• Evonik Degussa Gmbh

Inventors

• Lobert Matthias
• Zellmer Volker
• Brösgen Anja
• Reibold Thomas

Classifications

• C08G65/336

  containing silicon · CPC title

• C08G2650/58

  Ethylene oxide or propylene oxide copolymers, e.g. pluronics · CPC title

• C08G65/337

  containing other elements (organic compounds containing halogens only as halides of a carboxyl group C08G65/332) · CPC title

• C08G65/324 Primary

  containing oxygen · CPC title

• C08G65/2603

  the other compounds containing oxygen · CPC title