SILICONE HYDROGEL LENS WITH A CROSSLINKED HYDROPHILIC COATING
First Claim
1. A method for producing silicone hydrogel contact lenses with crosslinked hydrophilic coatings thereon, comprising the steps of:
- (a) obtaining a silicone hydrogel contact lens having amino groups and/or carboxyl groups on and/or near its surface and a water-soluble and thermally-crosslinkable hydrophilic polymeric material, wherein the silicone hydrogel contact lens comprises amino groups or carboxyl groups or both on and/or near the surface of the contact lens, wherein the hydrophilic polymeric material comprises (i) from about 20% to about 95% by weight of first polymer chains derived from an epichlorohydrin-functionalized polyamine or polyamidoamine, (ii) from about 5% to about 80% by weight of hydrophilic moieties or second polymer chains derived from at least one hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of amino group, carboxyl group, thiol group, and combination thereof, and (iii) positively-charged azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains, wherein the hydrophilic moieties or 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, carboxyl or thiol group of the hydrophilicity-enhancing agent; and
(b) heating the silicone hydrogel contact lens in an aqueous solution in the presence of the hydrophilic polymeric material to and at a temperature from about 40°
C. to about 140°
C. for a period of time sufficient to covalently attach the hydrophilic polymeric material onto the surface of the silicone hydrogel contact lens through second covalent linkages each formed between one azetidinium group of the hydrophilic polymeric material and one of the reactive functional groups on and/or near the surface of the contact lens, thereby forming a crosslinked hydrophilic coating on the silicone hydrogel contact lens, wherein the silicone hydrogel contact lens with the crosslinked hydrophilic coating thereon has a surface wettability characterized by having an averaged water contact angle of about 90 degrees or less.
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Accused Products
Abstract
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.
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Citations
20 Claims
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1. A method for producing silicone hydrogel contact lenses with crosslinked hydrophilic coatings thereon, comprising the steps of:
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(a) obtaining a silicone hydrogel contact lens having amino groups and/or carboxyl groups on and/or near its surface and a water-soluble and thermally-crosslinkable hydrophilic polymeric material, wherein the silicone hydrogel contact lens comprises amino groups or carboxyl groups or both on and/or near the surface of the contact lens, wherein the hydrophilic polymeric material comprises (i) from about 20% to about 95% by weight of first polymer chains derived from an epichlorohydrin-functionalized polyamine or polyamidoamine, (ii) from about 5% to about 80% by weight of hydrophilic moieties or second polymer chains derived from at least one hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of amino group, carboxyl group, thiol group, and combination thereof, and (iii) positively-charged azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains, wherein the hydrophilic moieties or 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, carboxyl or thiol group of the hydrophilicity-enhancing agent; and (b) heating the silicone hydrogel contact lens in an aqueous solution in the presence of the hydrophilic polymeric material to and at a temperature from about 40°
C. to about 140°
C. for a period of time sufficient to covalently attach the hydrophilic polymeric material onto the surface of the silicone hydrogel contact lens through second covalent linkages each formed between one azetidinium group of the hydrophilic polymeric material and one of the reactive functional groups on and/or near the surface of the contact lens, thereby forming a crosslinked hydrophilic coating on the silicone hydrogel contact lens, wherein the silicone hydrogel contact lens with the crosslinked hydrophilic coating thereon has a surface wettability characterized by having an averaged water contact angle of about 90 degrees or less. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
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19. An ophthalmic lens product, which comprises a sterilized and sealed lens package,
wherein the lens package comprises: -
a post-autoclave lens packaging solution and a readily-usable silicone hydrogel contact lens immersed therein, wherein the readily-usable silicone hydrogel contact lens comprises a crosslinked hydrophilic coating obtained by autoclaving an original silicone hydrogel contact lens having amino groups and/or carboxyl groups on and/or near the surface of the original silicone hydrogel contact lens in a pre-autoclave packaging solution containing a water-soluble and thermally-crosslinkable hydrophilic polymeric material, wherein the thermally-crosslinkable hydrophilic polymeric material comprises (i) from about 20% to about 95% by weight of first polymer chains derived from an epichlorohydrin-functionalized polyamine or polyamidoamine, (ii) from about 5% to about 80% by weight of hydrophilic moieties or second polymer chains derived from at least one hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of amino group, carboxyl group, thiol group, and combination thereof, and (iii) azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains, wherein the thermally-crosslinkable hydrophilic polymeric material is covalently attached onto the original silicone hydrogel contact lens through first covalent linkages each formed between one amino or carboxyl group on and/or near the surface of the original silicone hydrogel contact lens and one azetidinium group of the thermally-crosslinkable hydrophilic polymeric material, wherein the post-autoclave packaging solution comprises at least one buffering agent in an amount sufficient to maintain a pH of from about 6.0 to about 8.5 and has a tonicity of from about 200 to about 450 milliosmol, and a viscosity of from about 1 centipoise to about 20 centipoises at 25°
C.,wherein the post-autoclave packaging solution comprises a polymeric wetting material which is an hydrolyzed product of the thermally-crosslinkable hydrophilic polymeric material after autoclave, wherein the readily-usable silicone hydrogel contact lens has a surface hydrophilicity/wettability characterized by having an averaged water contact angle of about 90 degrees or less.
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20. A water-soluble and thermally-crosslinkable hydrophilic polymeric material, comprising:
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(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 at least one hydrophilicity-enhancing polymeric agent having at least one reactive functional group selected from the group consisting of amino group, carboxyl group, thiol group, and combination thereof, 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, carboxyl or thiol group of the hydrophilicity-enhancing polymeric agent; and (c) azetidinium groups which are parts of the first polymer chains or pendant groups covalently attached to the first polymer chains.
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Specification