Silicone hydrogel lens with a crosslinked hydrophilic coating
View Patent ↗The invention is related to a cost-effective method for making a silicone hydrogel contact lens having a crosslinked hydrophilic coating thereon. A method of the invention involves heating a silicone hydrogel contact lens in an aqueous solution in the presence of a water-soluble, highly branched, thermally-crosslinkable hydrophilic polymeric material having positively-charged azetidinium groups, to and at a temperature from about 40° C. to about 140° C. for a period of time sufficient to covalently attach the thermally-crosslinkable hydrophilic polymeric material onto the surface of the silicone hydrogel contact lens through covalent linkages each formed between one azetidinium group and one of the reactive functional groups on and/or near the surface of the silicone hydrogel contact lens, thereby forming a crosslinked hydrophilic coating on the silicone hydrogel contact lens. Such method can be advantageously implemented directly in a sealed lens package during autoclave.
1. A readily-usable silicone hydrogel contact lens, comprising:
a preformed silicone hydrogel contact lens; and
a crosslinked hydrophilic coating on the preformed silicone hydrogel contact lens,
wherein the crosslinked hydrophilic coating comprises from about 5% to about 80% by weight of polymer chains derived from a copolymer which is a polymerization product of a composition comprising from about 0.1% to about 30% by weight of one or more reactive vinylic monomer and (2) at least one phosphorylcholine-containing vinylic monomer, wherein said one or more reactive vinylic monomers are vinylic monomers having a carboxyl group or an amino group,
wherein the readily-usable silicone hydrogel contact lens has (1) an averaged water contact angle of about 80 degrees or less, (2) an oxygen permeability of at least about 40 barrers, (3) an elastic modulus of about 1.5 MPa or less, and (4) a water content of from about 18% to about 70% by weight when fully hydrated.
2. The readily-usable silicone hydrogel contact lens of claim 1 , wherein the readily-usable silicone hydrogel contact lens has an averaged water contact angle of about 70 degrees or less.
3. The readily-usable silicone hydrogel contact lens of claim 1 , wherein the readily-usable silicone hydrogel contact lens has an averaged water contact angle of about 60 degrees or less.
4. The readily-usable silicone hydrogel contact lens of claim 1 , wherein the readily-usable silicone hydrogel contact lens has an averaged water contact angle of about 50 degrees or less.
5. The readily-usable silicone hydrogel contact lens of claim 1 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
6. The readily-usable silicone hydrogel contact lens of claim 2 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
7. The readily-usable silicone hydrogel contact lens of claim 3 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
8. The readily-usable silicone hydrogel contact lens of claim 4 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
9. The readily-usable silicone hydrogel contact lens of claim 1 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
10. The readily-usable silicone hydrogel contact lens of claim 2 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
11. The readily-usable silicone hydrogel contact lens of claim 3 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
12. The readily-usable silicone hydrogel contact lens of claim 4 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
13. The readily-usable silicone hydrogel contact lens of claim 5 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
14. The readily-usable silicone hydrogel contact lens of claim 6 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
15. The readily-usable silicone hydrogel contact lens of claim 7 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
16. The readily-usable silicone hydrogel contact lens of claim 8 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
17. The readily-usable silicone hydrogel contact lens of claim 9 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
18. The readily-usable silicone hydrogel contact lens of claim 10 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
19. The readily-usable silicone hydrogel contact lens of claim 11 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
20. The readily-usable silicone hydrogel contact lens of claim 12 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.