Silicone compound and a use thereof

Patent metadata

Field	Value
Publication number	US-9353135-B2
Application number	US-201514658799-A
Country	US
Kind code	B2
Filing date	Mar 16, 2015
Priority date	Mar 20, 2014
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

One of the purposes of the present invention is to provide a compound which is a polymerizable monomer having a specific number of silicon atoms and a specific number of fluorine atoms and to provide a method for preparing the compound. The present invention provides a compound represented by the following formula (1):

wherein m is an integer of from 2 to 10, n is an integer of from 1 to 3, R 1 is, independently of each other, an alkyl group having 1 to 6 carbon atoms, and R 2 is, independently of each other, an alkylene group having 1 to 6 carbon atoms or a fluoroalkylene group having 1 to 6 carbon atoms, R 3 is an alkyl group having 1 to 4 carbon atoms, and R 4 , R 5 and R 6 are, independently of each other, a hydrogen atom or a methyl group.

First claim

The invention claimed is:

1. A compound mixture having the following formula (1):

wherein m is an integer of from 2 to 10, n is an integer of from 1 to 3, R 1 is, independently of each other, an alkyl group having 1 to 6 carbon atoms, R 2 is, independently of each other, an alkylene group having 1 to 6 carbon atoms or a fluoroalkylene group having 1 to 6 carbon atoms, R 3 is an alkyl group having 1 to 4 carbon atoms, and R 4 , R 5 and R 6 are, independently of each other, a hydrogen atom or a methyl group,
wherein more than 95 mass % of a total mass of the compound mixture having the formula (1) consists of a structure having a single value for m and a single value for n in the formula (1).

2. The compound mixture according to claim 1 , wherein m in the formula (1) is 3.

3. A polymer having repeating units derived from the compound mixture according to claim 1 and repeating units derived from at least one other compound having a group which is polymerizable with said compound.

4. An ophthalmic device composed of the polymer according to claim 3 .

5. A method for preparing the compound of claim 1 having the following formula (1):

wherein m is an integer of from 2 to 10, n is an integer of from 1 to 3, R 1 is, independently of each other, an alkyl group having 1 to 6 carbon atoms, R 2 is, independently of each other, an alkylene group having 1 to 6 carbon atoms or a fluoroalkylene group having 1 to 6 carbon atoms, R 3 is an alkyl group having 1 to 4 carbon atoms, and R 4 , R 5 and R 6 are, independently of each other, a hydrogen atom or a methyl group,
comprising a step of reacting a silicone compound having the following formula (2):

wherein m, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined above;
with a (meth)acryl acid halide having the following formula (3):

wherein X is a Cl, Br or I atom and R 6 is as defined above.

6. The method according to claim 5 , wherein said reaction is carried out in the presence of an acid scavenger.

7. The method according to claim 6 , wherein the acid scavenger is triethylamine.

8. The method according to claim 5 , wherein the method comprises a step of reacting a polyorganohydrogen siloxane having the following formula (4):

wherein m, R 1 , R 2 and R 3 are as defined above;
with a compound having the following formula (5):

wherein n, R 4 and R 5 are as defined above;
to thereby prepare the silicone compound having the aforesaid formula (2).

9. The method according to claim 8 , wherein an amount of one kind of compound having each one value of m and n in the formula (2) is more than 95 mass % of a total mass of the compound.

10. A method for preparing a compound having the following formula (1):

wherein m is an integer of from 2 to 10, n is an integer of from 1 to 3, R 1 is, independently of each other, an alkyl group having 1 to 6 carbon atoms, R 2 is, independently of each other, an alkylene group having 1 to 6 carbon atoms or a fluoroalkylene group having 1 to 6 carbon atoms, R 3 is an alkyl group having 1 to 4 carbon atoms, and R 4 , R 5 and R 6 are, independently of each other, a hydrogen atom or a methyl group,
comprising a step of reacting a polyorganohydrogen siloxane having the following formula (4):

wherein m, R 1 , R 2 and R 3 are as defined above;
with a compound having the following formula (6):

wherein n, R 4 and R 5 are as defined above.

11. The method according to claim 5 , wherein an amount of one kind of compound having each one value of m and n in the formula (1) is more than 95 mass % of a total mass of the compound.

12. The method according to claim 5 , wherein m in the formula (1) is 3.

Assignees

• Shinetsu Chemical Co

Inventors

• Kudo Muneo
• Ichinohe Shoji
• Goto Tomoyuki

Classifications

• C07F7/1804

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

• C08L83/12

  containing polyether sequences · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C08G77/24

  halogen-containing groups · CPC title

• C07F7/0838 Primary

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title