Alkyl silikate

Patent metadata

Field	Value
Publication number	US-12466920-B2
Application number	US-202018016694-A
Country	US
Kind code	B2
Filing date	Jul 22, 2020
Priority date	Jul 22, 2020
Publication date	Nov 11, 2025
Grant date	Nov 11, 2025

Abstract

Alkyl-silicates and alkyl-silicate-containing organosilicon compounds. The alkyl-silicate-containing organosilicon compound includes at least 90% by weight, preferably at least 95% by weight, of alkyl silicates of average formula (I)

[SiO 4/2 ] a [(R x O)SiO 3/2 ] b [(R y O)SiO 3/2 ] b ′[(R x O) 2 SiO 2/2 ] c

[(R x O)(R y O)SiO 2/2 ] c ′[(R y O) 2 SiO 2/2 ] c ″[(R x O) 3 SiO 1/2 ] d

[(R x O) 2 (R y O)SiO 1/2 ] d ′[(R x O)(R y O) 2 SiO 1/2 ] d ″

[(R y O) 3 SiO 1/2 ]d′″  (I).

Where the radicals R x are each independently selected from radicals that meet at least one of the following conditions: (a) where R x is a substituted or unsubstituted, C 4 -C 20 hydrocarbon radical that is branched at the α-carbon atom, (b) where R x is a substituted or unsubstituted, C 5 -C 20 hydrocarbon radical that is doubly branched at the β-carbon atom, and/or (c) where R x is an unsubstituted or alkyl-substituted cyclopentyl, cyclohexyl or cycloheptyl radical having a total of not more than 9 carbon atoms. Where the radicals R y are each independently selected from (i) hydrogen, (ii) methyl radical, and (iii) ethyl radical.

First claim

The invention claimed is:

1 . An alkyl-silicate-containing organosilicon compound, comprising:
wherein the alkyl-silicate-containing organosilicon compound comprises at least 90% by weight, preferably at least 95% by weight, of alkyl silicates of average formula (I)
[SiO 4/2 ] a [(R x O)SiO 3/2 ] b [(R y O)SiO 3/2 ] b ′[(R x O) 2 SiO 2/2 ] c

[(R x O)(R y O)SiO 2/2 ] c ′[(R y O) 2 SiO 2/2 ] c ″[(R x O) 3 SiO 1/2 ] d

[(R x O) 2 (R y O)SiO 1/2 ] d ′[(R x O)(R y O) 2 SiO 1/2 ] d ″

[(R y O) 3 SiO 1/2 ]d′″  (I);

wherein the indices a, b, b′, c, c′, c″, d, d′, d″, d′″ indicate the average content of the respective structural unit in the compound and are each independently a number within a range from 0 to 100 000, and wherein the sum of the indices is at least 2; wherein the radicals R x are each independently selected from radicals that meet at least one of the following conditions: (a) R x is a substituted or unsubstituted, C 4 -C 20 hydrocarbon radical that is branched at the α-carbon atom, (b) R x is a substituted or unsubstituted, C 5 -C 20 hydrocarbon radical that is doubly branched at the β-carbon atom, and/or (c) R x is an unsubstituted or alkyl-substituted cyclopentyl, cyclohexyl or cycloheptyl radical having a total of not more than 9 carbon atoms; wherein substituted in each case means that the hydrocarbon radical has at least one functional group selected from the group consisting of vinyl radical, ethynyl radical, amino radical, epoxy radical, thiol radical, and carbinol radical; wherein the radicals R y are each independently selected from the group consisting of (i) hydrogen, (ii) methyl radical, and (iii) ethyl radical; wherein the molar proportion of all radicals R y in the silicate is within a range from 1 to 15 mol %; wherein the molar proportion for R y =(i) hydrogen is not more than 9 mol %, in each case based on the molar amount of the sum of all radicals R x and R y ; and wherein the alkyl-silicate-containing organosilicon compounds contain no SiC-bonded radicals.

2 . The alkyl-silicate-containing organosilicon compound of claim 1 , wherein the radicals R y are each independently a (ii) methyl radical or (iii) ethyl radical.

3 . The alkyl-silicate-containing organosilicon compound of claim 1 , wherein the radicals R x are each independently selected from radicals that meet one of the following conditions:
(a) R x is a substituted or unsubstituted, aliphatic C 4 -C 10 hydrocarbon radical that is branched at the α-carbon atom, (b) R x is a substituted or unsubstituted, aliphatic C 5 -C 10 hydrocarbon radical that is doubly branched at the β-carbon atom, and (c) R x is an unsubstituted or alkyl-substituted cyclohexyl radical having a total of not more than 9 carbon atoms.

4 . The alkyl-silicate-containing organosilicon compound of claim 1 , wherein the radicals R x are selected from the group consisting of 2-butyl radical, 3-methyl-2-butyl, 3-methyl-2-pentyl, 3-pentyl radical, 2-hexyl radical, 3-hexyl radical, 2-heptyl radical, 2-octyl radical, 1-phenylethyl radical, 1-phenyl-1-propyl radical, 2,2-dimethyl-1-propyl radical, 1,1-dimethylethyl radical, 1,1-dimethylpropyl radical, cyclohexyl radical, and 3,3,5-trimethylcyclohexyl radical.

5 . The alkyl-silicate-containing organosilicon compound of claim 1 , wherein the indices a, b, b′, c, c′, c″, d, d′, d″, d′″ are each independently a number within a range from 0 to 500, and wherein the sum of the indices is at least 2.

6 . The alkyl-silicate-containing organosilicon compound of claim 1 , wherein the indices a, b, b′, c, c′, c″, d, d′, d″, d′″ are each independently a number within a range from 0 to 10, and wherein the sum of the indices is at least 2.

7 . An alkyl silicate, comprising:
wherein the alkyl silicate has the average formula (I)
[SiO 4/2 ] a [(R x O)SiO 3/2 ] b [(R y O)SiO 3/2 ] b ′[(R x O) 2 SiO 2/2 ] c

[(R x O)(R y O)SiO 2/2 ] c ′[(R y O) 2 SiO 2/2 ] c ″[(R x O) 3 SiO 1/2 ] d

[(R x O) 2 (R y O)SiO 1/2 ] d ′[(R x O)(R y O) 2 SiO 1/2 ] d ″

[(R y O) 3 SiO 1/2 ]d′″  (I);

wherein the indices a, b, b′, c, c′, c″, d, d′, d″, d′″ indicate the average content of the respective structural unit in the compound and are each independently a number within a range from 0 to 100 000, wherein the sum of the indices is at least 2; wherein the radicals R x are each independently selected from radicals that meet at least one of the following conditions: (a) R x is a substituted or unsubstituted, C 4 -C 20 hydrocarbon radical that is branched at the α-carbon atom, (b) R x is a substituted or unsubstituted, C 5 -C 20 hydrocarbon radical that is doubly branched at the β-carbon atom, and/or (c) R x is an unsubstituted or alkyl-substituted cyclopentyl, cyclohexyl or cycloheptyl radical having a total of not more than 9 carbon atoms; wherein substituted in each case means that the hydrocarbon radical has at least one functional group selected from the group consisting of vinyl radical, ethynyl radical, amino radical, epoxy radical, thiol radical, and carbinol radical; wherein the radicals R y are each independently selected from the group consisting of (i) hydrogen, (ii) methyl radical, and (iii) ethyl radical; wherein the molar proportion of all radicals R y in the silicate is within a range from 1 to 15 mol %; and wherein the molar proportion for R y =(i) hydrogen is not more than 9 mol %, in each case based on the molar amount of the sum of all radicals R x and R y .

8 . The alkyl silicate of claim 7 , wherein the radicals R y are each independently a (ii) methyl radical or (iii) ethyl radical.

9 . The alkyl silicate of claim 7 , wherein the radicals R x are each independently selected from radicals that meet one of the following conditions:
(a) R x is a substituted or unsubstituted, aliphatic C 4 -C 10 hydrocarbon radical that is branched at the α-carbon atom, (b) R x is a substituted or unsubstituted, aliphatic C 5 -C 10 hydrocarbon radical that is doubly branched at the β-carbon atom, and (c) R x is an unsubstituted or alkyl-substituted cyclohexyl radical having a total of not more than 9 carbon atoms.

10 . The alkyl silicate of claim 7 , wherein the radicals R x are selected from the group consisting of 2-butyl radical, 3-methyl-2-butyl, 3-methyl-2-pentyl, 3-pentyl radical, 2-hexyl radical, 3-hexyl radical, 2-heptyl radical, 2-octyl radical, 1-phenylethyl radical, 1-phenyl-1-propyl radical, 2,2-dimethyl-1-propyl radical, 1,1-dimethylethyl radical, 1,1-dimethylpropyl radical, cyclohexyl radical, and 3,3,5-trimethylcyclohexyl radical.

11 . The alkyl silicate of claim 7 , wherein the indices a, b, b′, c, c′, c″, d, d′, d″, d′″ are each independently a number within a range from 0 to 500, and wherein the sum of the indices is at least 2.

12 . The alkyl silicate of claim 7 , wherein the indices a, b, b′, c, c′, c″, d, d′, d″, d′″ are each independently a number within a range from 0 to 10, and wherein the sum of the indices is at least 2.

Assignees

• Wacker Chemie Ag

Inventors

• Fritz-Langhals Elke
• Weidner Richard

Classifications

• C08L83/04

  Polysiloxanes · CPC title

• C08G77/02 Primary

  Polysilicates · CPC title

• C08G77/18 Primary

  to alkoxy or aryloxy groups · CPC title