Method for producing silicon compound

Patent metadata

Field	Value
Publication number	US-9738789-B2
Application number	US-201615162908-A
Country	US
Kind code	B2
Filing date	May 24, 2016
Priority date	Dec 13, 2013
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

To provide a method for producing a silicon compound, whereby a hydrosilylation reaction of a compound having a 2-propenyl group, can be conducted with high selectivity by a simple and easy method. The method for producing a silicon compound comprises reacting a compound (3) having a group represented by —CH 2 CH═CH 2 and a silicon compound (4) having an H—Si bond in the presence of a transition metal catalyst (C) and a compound (D) having a group represented by —S(═O)— to obtain a compound (5) having a group represented by —CH 2 CH 2 CH 2 Si≡.

First claim

What is claimed is:

1. A method for producing a silicon compound, comprising reacting a compound having a group represented by formula (3) and a silicon compound (4) having an H—Si bond in the presence of a transition metal catalyst (C) and dimethyl sulfoxide or tetramethylene sulfoxide to obtain a compound having a group represented by formula (5):
—CH 2 CH═CH 2   (3)

—CH 2 CH 2 CH 2 Si≡  (5).

2. The method according to claim 1 , wherein the silicon compound (4) having an H—Si bond is a compound represented by formula (41), and the group represented by the formula (5) is a group represented by formula (5-1):
HSiL m R n   (41)

—CH 2 CH 2 CH 2 SiL m R n   (5-1)

wherein L a hydrolyzable group, R is a monovalent hydrocarbon group, m is an integer of from 1 to 3, and n is an integer of from 0 to 2, provided m+n=3.

3. The method according to claim 2 , wherein L is a C 1-4 alkoxy group.

4. The method according to claim 1 , wherein the silicon compound (4) having an H—Si bond is a linear or cyclic organopolysiloxane compound.

5. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound having an allyloxy group.

6. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound having from 1 to 3 groups represented by the formula (3).

7. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound having a polyoxyalkylene chain or a polyoxyfluoroalkylene chain.

8. The method according to claim 1 , wherein the number average molecular weight of the compound having a group represented by the formula (3) is from 200 to 20,000.

9. The method according to claim 1 , wherein the transition metal catalyst (C) is a platinum catalyst.

10. The method according to claim 9 , wherein the transition metal catalyst (C) is a Pt/divinyltetramethyldisiloxane complex or a Pt/tetramethyltetravinylcyclotetrasiloxane complex.

11. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound represented by formula (3A), a compound represented by formula (3B), or a compound represented by formula (3C):
R A —CH 2 CH═CH 2   (3A)

CH 2 ═CHCH 2 —R B —CH 2 CH═CH 2   (3B)

wherein each of R A and R B is an organic group having a polyoxyalkylene chain or a polyoxyfluoroalkylene chain, and R C is a trivalent organic group.

12. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound represented by formula (3A) or a compound represented by formula (3B):
R A —CH 2 CH═CH 2   (3A)

CH 2 ═CHCH 2 —R B —CH 2 CH═CH 2   (3B)

wherein each of R A and R B is an organic group having a polyoxyfluoroalkylene chain.

13. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound represented by formula (3A):
R A —CH 2 CH═CH 2   (3A)

wherein R A is CH 3 —R A1 —O—, CH 3 —R A1 —O—(C y H 2y O) yl —, CH 3 —R A1 —, CF 3 —R A1 —O—, CF 3 —R A1 —O—(C y H 2y O) y1 —, CF 3 —R A1 —O—(C σ F 2σ O) σ1 —, CF 3 —R A1 —, A-O-Q-(C b F 2b O) d —X—O—, or a group represented by any one of following formulae:

wherein:
R A1 is a single bond, a C 1-30 alkylene group, or a C 1-30 fluoroalkylene group, and the number of carbon atoms in the alkylene group or the fluoroalkylene group is 1 to 20;
each of y and σ is independently an integer of from 1 to 10;
each of y1 and σ1 is independently an integer of from 1 to 500;
A is a C 1-20 perfluoroalkyl group;
Q is a single bond, —CH 2 —, —CH—, -Q 1 -CH 2 —, -Q 1 -CHF—, -Q 1 -O—CH 2 —, -Q 1 -O—CHF—, -Q 1 CH 2 —O— or -Q 1 -CHF—O—;
Q 1 is a C 1-10 fluoroalkylene group, a group in which an etheric oxygen atom is inserted between two carbon atoms of a C 2-10 fluoroalkylene group, a C 1-10 alkylene group, or a group in which an etheric oxygen atom is inserted between two carbon atoms of a C 2-10 alkylene group;
b is an integer of from 1 to 10;
d is an integer of from 1 to 200, provided that when d is at least 2, (C b F 2b O) d is optionally composed of at least two kinds of C b F 2b O different in b; and
X is a divalent organic group having no CF 2 O.

14. The method according to claim 1 , wherein the compound having a group represented by the formula (3) is a compound represented by formula (3B):
CH 2 ═CHCH 2 —R B —CH 2 CH═CH 2   (3B)

wherein:
R B is a single bond, —O—, —O—R B1 —O—, —O—(C y H 2y O) y1 —, —O—R B1 , —O—(C y H 2y O) y1 —, R B1 , —R B1 —O—, —O—R B1 —, —R B1 —O—(C y H 2y O) y1 —, or —O-Q-(C b F 2b O) d —X—O—;
R B1 is a C 1-30 alkylene group, or a C 1-30 fluoroalkylene group, and the number of carbon atoms in the alkylene group or the fluoroalkylene group is 1 to 20;
y is an integer of from 1 to 10;
y1 is an integer of from 1 to 500;
Q is a single bond,
Q is a single bond, —CH 2 —, —CHF—, -Q 1 -CH 2 —, -Q 1 -CHF—, -Q 1 -O—CH 2 —, -Q 1 -O—CHF—, -Q 1 CH 2 —O— or -Q 1 -CHF—O—;
Q 1 is a C 1-10 fluoroalkylene group, a group in which an etheric oxygen atom is inserted between two carbon atoms of a C 2-10 fluoroalkylene group, a C 1-10 alkylene group, or a group in which an etheric oxygen atom is inserted between two carbon atoms of a C 2-10 alkylene group;
b is an integer of from 1 to 10;
d is an integer of from 1 to 200, provided that when d is at least 2, (C b F 2b O) d is optionally composed of at least two kinds of C b F 2b O different in b; and
X is a divalent organic group having no CF 2 O.

15. The method according to claim 1 , wherein a selectivity of the reaction to obtain the compound having the group represented by formula (5) is 95% or more.

Assignees

• Asahi Glass Co Ltd

Inventors

• Hoshino Taiki
• Murotani Eisuke
• Isobe Akira

Classifications

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C09D4/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title

• C09D171/02 Primary

  Polyalkylene oxides · CPC title

• C08L71/02

  Polyalkylene oxides · CPC title