Silicone-containing ocular lens material with high safety and preparing method thereof
[Problem] To provide a safe ocular lens material having high oxygen permeability, excellent surface wettability, the excellent lubricity/easy lubricating property of surface, little in surface adhesive and superior flexibility and stress relaxation, in addition, suppressing elution of a monomer from the final product. [Means for Solving the Problem] An ocular lens comprising a compound (A) having an ethylenically unsaturated group and polydimethylsiloxane structure through a urethane bond and an 1-alkyl-3-methylene-2-pyrrolidone (B). [Selected Figure] None
1. An ocular lens material comprising at least one kind of a compound (A) having an ethylenically unsaturated group and polydimethylsiloxane structure through a urethane bond; at least one kind of a pyrrolidone derivative (B) selected from the group consisting of 1-alkyl-3-methylene-2-pyrrolidone, 1-alkyl-5-methylene-2-pyrrolidone, and 5-alkyl-3-methylene-2-pyrrolidone; silicone compound (C) being tris(trimethylsiloxy)silylpropyl(meth)acrylate; and an N-substituted acrylamide (D),
wherein an oxygen permeability coefficient (Dk) of the ocular lens material is not less than 51 (×10 −11 (cm 2 /sec)), and
wherein a water content of the ocular lens material is 32% to 55% by weight.
2. An ocular lens material according to claim 1 , comprising 5 to 60% by weight of the pyrrolidone derivatives.
3. An ocular lens material according to claim 1 , wherein the pyrrolidone derivative (B) is 1-methyl-3-methylene-2-pyrrolidone.
4. An ocular lens material according to claim 1 , wherein the pyrrolidone derivative (B) is 1-methyl-5-methylene-2-pyrrolidone.
5. An ocular lens material according to claim 1 , wherein the pyrrolidone derivative (B) is 5-methyl-3-methylene-2-pyrrolidone.
6. An ocular lens material according to claim 1 , wherein the repeating number of siloxane of the polydimethylsiloxane structure in a compound (A) having ethylenically unsaturated groups and polydimethylsiloxane structure through a urethane bond is 10 to 100.
7. An ocular lens material according to claim 1 , wherein tensile modulus is 0.2 to 0.8 MPa and stress relaxation under loading a fixed load for 30 seconds is 8 to 15%.
8. An ocular lens material according to claim 1 , wherein the N-substituted acrylamide (D) is at least one of N-substituted acrylamides selected from the group consisting of N,N-dimethyl acrylamide, N,N-diethyl acrylamide, acryloyl morpholine, N-isopropyl acrylamide and N-(2-hydroxyethyl)acrylamide.
9. An ocular lens material according to claim 1 , wherein at least one of a crosslinking agent is further comprised.
10. A lens for the eyes comprising the ocular lens material according to claim 1 .
11. A method for preparing an ocular lens material, comprising
a) a step of obtaining a mixed solution comprising at least one kind of a compound (A) having ethylenically unsaturated groups and polydimethylsiloxane structures through a urethane bond and at least one kind of a pyrrolidone derivative (B) selected from the group consisting of 1-alkyl-3-methylene-2-pyrrolidone, 1-alkyl-5-methylene-2-pyrrolidone, and 5-alkyl-3-methylene-2-pyrrolidone and silicone compound (C) being tris(trimethylsiloxy)silylpropyl(meth)acrylate and an N-substituted acrylamide (D), and a photo polymerization initiator and/or a thermal polymerization initiator,
b) a step of introducing said mixed solution to a mold,
c) a step of obtaining an ocular lens material cured by irradiating UV light on and/or heating the mixed solution in said mold,
d) a step of carrying out surface treatment to said ocular lens material after demolding said ocular lens material to impart hydrophilicity and deposit resistance,
e) a step of removing an unreacted component from said ocular lens material, and
f) a step of hydrating said ocular lens material,
wherein an oxygen permeability coefficient (Dk) of the ocular lens material is not less than 51 (×10 −11 (cm 2 /sec)), and
wherein a water content of the ocular lens material is 32% to 55% by weight.
12. A method for preparing the ocular lens material according to claim 11 , containing a crosslinking agent in the mixed solution.
13. A method for preparing the ocular lens material according to claim 11 , containing at least one of polymerizable or non polymerizable ultraviolet absorbents and/or at least one of polymerizable or non polymerizable dyes in the mixed solution.
14. A method for preparing the ocular lens material according to claim 11 , comprising 0.1 to 5% by weight of a water-soluble organic solvent.
15. A method for preparing the ocular lens material according to claim 14 , wherein the water-soluble organic solvent is a water-soluble organic solvent selected from alcohols having 1 to 4 carbons, acetone, methyl ethyl ketone, dimethylformamide, dimethylsulfoxide, acetonitrile and N-methyl-2-pyrrolidone.
16. A method for preparing the ocular lens material according to claim 11 , wherein the surface treatment is plasma treatment.
17. A method for preparing the ocular lens material according to claim 16 , wherein oxygen or a mixture of oxygen is used in the plasma treatment.
18. A method for preparing the ocular lens material according to claim 17 , wherein a mixture of oxygen and water is used in the plasma treatment.
19. A method for preparing the ocular lens material according to claim 17 , wherein a mixture of oxygen and tetrafluoromethane is used in the plasma treatment.
20. A method for preparing the ocular lens material according to claim 17 , wherein a mixture of oxygen and organic silane is used in the plasma treatment.
21. A method for preparing the ocular lens material according to claim 20 , wherein the organic silane is tetramethoxysilane.
22. A method for preparing the ocular lens material according to claim 17 , wherein a mixture of oxygen and methane is used in the plasma treatment.
23. A method for preparing the ocular lens material according to claim 17 , wherein a mixture of oxygen, nitrogen and methane is used in the plasma treatment.
24. A method for preparing the ocular lens material according to claim 11 , wherein the surface treatment is a treatment according to the coating method of a hydrophilic polymer coating.
25. A method for preparing the ocular lens material according to claim 24 , wherein the coating method is a plasma polymerization method of a hydrophilic monomer.
26. A method for preparing the ocular lens material according to claim 24 , wherein the coating method is a plasma-induced graft polymerization.
27. A method for preparing the ocular lens material according to claim 11 , further comprising (g) a step of coloring the ocular lens material by using a vat dye.
28. A method for preparing an ocular lens material, comprising
a) a step of obtaining a mixed solution comprising at least one kind of a compound (A) having ethylenically unsaturated groups and polydimethylsiloxane structures through a urethane bond and at least one kind of a pyrrolidone derivative (B) selected from the group consisting of 1-alkyl-3-methylene-2-pyrrolidone, 1-alkyl-5-methylene-2-pyrrolidone, and 5-alkyl-3-methylene-2-pyrrolidone and silicone compound (C) being tris(trimethylsiloxy)silylpropyl(meth)acrylate and an N-substituted acrylamide (D), and a photo polymerization initiator and/or a thermal polymerization initiator,
b) a step of introducing said mixed solution to a mold,
c) a step of obtaining an ocular lens material cured by irradiating UV light on and/or heating the mixed solution in said mold,
d) a step of carrying out surface treatment to said ocular lens material after demolding said ocular lens material to impart hydrophilicity and deposit resistance, and
e) a step of removing an unreacted component from said ocular lens material and a step of hydrating said ocular lens material, at the same time by immersing in distilled water or a saline solution,
wherein an oxygen permeability coefficient (Dk) of the ocular lens material is not less than 51 (×10 −11 (cm 2 /sec)), and
wherein a water content of the ocular lens material is 32% to 55% by weight.