Amino-containing organosilicon compound and making method

Patent metadata

Field	Value
Publication number	US-10065975-B2
Application number	US-201615200132-A
Country	US
Kind code	B2
Filing date	Jul 1, 2016
Priority date	Jul 3, 2015
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

An amino-containing organosilicon compound having formula (1) is used for surface treatment of an inorganic filler for thereby rendering the filler more compatible with and adhesive to a polymer material. In formula (1), R 1 is alkyl, alkenyl, aryl or aralkyl, R 2 is alkenyl, aryl or aralkyl, R 3 and R 4 each are a monovalent hydrocarbon group, and n is 0, 1 or 2.

First claim

The invention claimed is:

1. An amino-containing organosilicon compound having the general formula (1):

wherein
R 1 is an unsubstituted C 1 -C 10 alkyl or C 2 -C 10 alkenyl group,
R 2 is an unsubstituted C 2 -C 10 alkenyl or C 6 -C 10 aryl group,
R 3 and R 4 are each independently an unsubstituted C 1 -C 10 alkyl group, and
n is an integer of 0 to 2.

2. A method for preparing the amino-containing organosilicon compound of claim 1 , comprising the steps of
reacting an amine compound with a γ-glycidoxypropylalkoxysilane, and subjecting the resulting reaction mixture to dealcoholization cyclization under solvent reflux,
the amine compound having the general formula (2):

wherein R 1 is an unsubstituted C 1 -C 10 alkyl or C 2 -C 10 alkenyl group and R 2 is an unsubstituted C 2 -C 10 alkenyl or C 6 -C 10 aryl group, and
the γ-glycidoxypropylalkoxysilane having the general formula (3):

wherein R 3 and R 4 are each independently an unsubstituted C 1 -C 10 alkyl group, and n is an integer of 0 to 2.

3. A method for preparing the amino-containing organosilicon compound of claim 1 , comprising the step of
reacting an amine compound with a γ-glycidoxypropylalkoxysilane while simultaneously effecting dealcoholization cyclization under solvent reflux,
the amine compound having the general formula (2):

wherein R 1 is an unsubstituted C 1 -C 10 alkyl or C 2 -C 10 alkenyl group and R 2 is an unsubstituted C 2 -C 10 alkenyl or C 6 -C 10 aryl group, and
the γ-glycidoxypropylalkoxysilane having the general formula (3):

wherein R 3 and R 4 are each independently an unsubstituted C 1 -C 10 alkyl group, and n is an integer of 0 to 2.

4. The method of claim 2 wherein the dealcoholization cyclization is effected in the presence of a basic catalyst.

5. The method of claim 3 wherein the dealcoholization cyclization is effected in the presence of a basic catalyst.

6. The amino-containing organosilicon compound of claim 1 , wherein R 1 is vinyl or allyl, R 2 is vinyl, allyl, or phenyl, and R 3 and R 4 are independently methyl or ethyl.

7. The amino-containing organosilicon compound of claim 1 , which is:
2,2-dimethoxy-8-(N,N-diallylaminomethyl)-1,6-dioxa-2-silacyclooctane;
2,2-dimethoxy-8-(N-methyl-N-phenylaminomethyl)-1,6-dioxa-2-silacyclooctane; or
2-ethoxy-2-methyl-8-(N,N-diallylaminomethyl)-1,6-dioxa-2-silacyclooctane.

Assignees

• Shinetsu Chemical Co

Inventors

• Honma Takayuki
• Kubota Tohru
• Tonomura Yoichi

Classifications

• C07F7/1804 Primary

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

• C08K5/54

  Silicon-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C07F7/1836

  Chemistry & Metallurgy · mapped topic

• C07F7/1812 Primary

  Chemistry & Metallurgy · mapped topic

• C07F7/184

  Chemistry & Metallurgy · mapped topic