Silicone compound and a use thereof
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.
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.