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 water-soluble and thermally-crosslinkable hydrophilic polymeric material, comprising:
(a) from about 20% to about 95% by weight of first polymer chains derived from an epichlorohydrin-functionalized polyamine or polyamidoamine;
(b) from about 5% to about 80% by weight of second polymer chains derived from a copolymer which is a polymerization product of a composition comprising about 50% or less 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 second polymer chains are covalently attached to the first polymer chains through one or more covalent linkages each formed between one azetitdinium group of the epichlorohydrin-functionalized polyamine or polyamidoamine and one amino or carboxyl group of the copolymer; and
(c) azetidinium groups which are parts of the first polymer chains or pendant groups covalently attached to the first polymer chains.
2. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 1 , wherein said one or more reactive vinylic monomers are vinylic monomers having a carboxyl group.
3. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 2 , wherein said one or more reactive vinylic monomers are selected from the group consisting of acrylic acid, C 1 -C 12 alkylacrylic acid, N,N-2-acrylamidoglycolic acid, beta methyl-acrylic acid, alpha-phenyl acrylic acid, beta-acryloxy propionic acid, sorbic acid, angelic acid, cinnamic acid, 1-carobxy-4-phenyl butadiene-1,3, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid, maleic acid, fumaric acid, tricarboxy ethylene, and combinations thereof.
4. The water-soluble and thermally-crosslinkable hydrophilic polymeric material, of claim 2 , wherein said one or more reactive vinylic monomers are selected from the group consisting of acrylic acid, C 1 -C 12 alkylacrylic acid, and combinations thereof.
5. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 1 , wherein said one or more reactive vinylic monomers are vinylic monomers having an amino group.
6. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 5 , wherein said one or more reactive vinylic monomers are selected from the group consisting of amino-C 1 -C 6 alkyl (meth)acrylate, C 1 -C 6 alkylamino-C 1 -C 6 alkyl (meth)acrylate, allylamine, vinylamine, amino-C 1 -C 6 alkyl (meth)acrylamide, C 1 -C 6 alkylamino-C 1 -C 6 alkyl (meth)acrylamide, and combinations thereof.
7. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 6 , wherein said one or more reactive vinylic monomers are amino-C 1 -C 6 alkyl (meth)acrylate, C 1 -C 6 alkylamino-C 1 -C 6 alkyl (meth)acrylate, or combinations thereof.
8. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 1 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
9. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 8 , wherein the composition comprises from about 0.1% to about 30% by weight of said one or more reactive vinylic monomers.
10. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 8 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
11. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 8 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
12. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 2 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
13. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 12 , wherein the composition comprises from about 0.1% to about 30% by weight of said one or more reactive vinylic monomers.
14. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 12 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
15. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 12 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
16. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 5 , wherein said at least one phosphorylcholine-containing vinylic monomer is (meth)acryloyloxyethyl phosphorylcholine.
17. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 16 , wherein the composition comprises from about 0.1% to about 30% by weight of said one or more reactive vinylic monomers.
18. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 16 , wherein the composition comprises from about 0.5% to about 20% by weight of said one or more reactive vinylic monomers.
19. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 16 , wherein the composition comprises from about 1% to about 15% by weight of said one or more reactive vinylic monomers.
20. The water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 1 , wherein said one or more reactive vinylic monomers are amino-C 2 -C 4 alkyl (meth)acrylate.