Phosphorylcholine group-containing polysiloxane monomer
Provided is a monomer suitable for application to an ophthalmic device, the monomer showing high surface hydrophilicity, a high oxygen transmissibility, and appropriate mechanical strength when copolymerized with a polymerizable monomer, such as a hydrophilic monomer. It has been recognized that a phosphorylcholine group-containing polysiloxane monomer can solve the problems.
1. A phosphorylcholine group-containing polysiloxane monomer, which is represented by the formula (1):
where “a” represents an integer of from 20 to 500, “b” represents an integer of from 1 to 70, “c” represents 0 or 1, “p” and “q” each represent 0 or 1, and X represents —CH 2 — or —CH 2 CH 2 —.
2. A method of producing a phosphorylcholine group-containing polysiloxane monomer represented by the formula (1), the method comprising a step of subjecting a hydrosilyl group-containing di-methacrylate-terminated silicone represented by the formula (4) and an allyl group-containing phosphorylcholine compound represented by the formula (5) to an addition reaction:
where “a” represents an integer of from 20 to 500, “b” represents an integer of from 1 to 70, “c” represents 0 or 1, “p” and “q” each represent 0 or 1, and X represents —CH 2 — or —CH 2 CH 2 —;
where “a” represents an integer of from 20 to 500, “b” represents an integer of from 1 to 70, and “p” and “q” each represent 0 or 1;
where “c” represents 0 or 1, and Z represents CH 2 ═CHCH 2 — or CH 2 ═CH—.
3. A monomer composition, comprising:
10 parts by weight to 60 parts by weight of a phosphorylcholine group-containing polysiloxane monomer represented by the formula (1); and
40 parts by weight to 90 parts by weight of one kind or a plurality of kinds of hydrophilic monomers:
where “a” represents an integer of from 20 to 500, “b” represents an integer of from 1 to 70, “c” represents 0 or 1, “p” and “q” each represent 0 or 1, and X represents —CH 2 — or —CH 2 CH 2 —.
4. The monomer composition according to claim 3 , wherein the hydrophilic monomers are any one or more selected from the group consisting of 2-hydroxyethyl (meth)acrylate, N-vinylpyrrolidone, N,N-dimethylacrylamide, 2-(methacryloyloxyethyl)-2-(trimethylammonioethyl) phosphate, methyl methacrylate, and hydroxypropyl (meth)acrylate.
5. A polymer, which is obtained by polymerizing the monomer composition of claim 3 .
6. A polymer, which is obtained by polymerizing the monomer composition of claim 4 .
7. The composition according to claim 1 , wherein the composition is a composition for an ophthalmic device.
8. The composition according to claim 3 , wherein the composition is a composition for an ophthalmic device.
9. An ophthalmic device, comprising the polymer of claim 4 .
10. An ophthalmic device, comprising the polymer of claim 5 .