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US 9,429,684 B2Granted
Primary amine-containing silicone hydrogel contact lenses and related compositions and methods
AssigneeCooperVision International Holding Company, LP
InventorsGuigui Wang, Hong Xue
Life of this patent
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Abstract
Miscible polymerizable compositions comprising at least one primary amine-containing methacrylate monomer, or at least one primary amine-containing methacrylamide monomer, in addition to 20-80 wt. % siloxane monomer, 20-80 wt. % hydrophilic monomer, cross-linking agent, and polymerization initiator, are described. These polymerizable compositions can be used to form silicone hydrogel contact lenses, and in methods of manufacturing silicone hydrogel contact lenses.
Claims22
A silicone hydrogel contact lens, comprising:
- a polymeric lens body having, when hydrated, an equilibrium water content of at least 30%, an oxygen permeability of at least 30 barrers, and a modulus of 0.3 to 1.2 MPa, and which is the reaction product of a miscible polymerizable composition, said miscible polymerizable composition comprising
- (a) at least one siloxane monomer in an amount of from 20 to 80 weight percent;
- (b) at least one hydrophilic monomer in an amount of from 20 to 80 weight percent;
- (c) at least one cross-linking agent;
- (d) at least one polymerization initiator;
- and
- (e) at least one primary amine-containing methacrylate monomer or at least one primary amine-containing methacrylamide monomer;
- wherein the polymeric lens body comprises a plurality of primary amine functional groups provided by polymerized units of the at least one primary amine-containing methacrylate monomer or polymerized units of the at least one primary amine-containing methacrylamide monomer, and the plurality of primary amine functional groups are covalently bonded with complementary functional groups as a result of the polymeric lens body having been provided in an aqueous solution comprising an agent having an attached one or more of said complementary functional groups.
5 more elements
A method of manufacturing a silicone hydrogel contact lens, comprising:
- providing a miscible polymerizable composition, said polymerizable composition comprising
- (a) at least one siloxane monomer in an amount of from 20 to 80 weight percent;
- (b) at least one hydrophilic monomer in an amount of from 20 to 80 weight percent;
- (c) at least one cross-linking agent;
- (d) at least one polymerization initiator;
- and
- (e) at least one primary amine-containing methacrylate monomer or at least one primary amine-containing methacrylamide monomer;
- polymerizing the polymerizable composition in a contact lens mold assembly to form a polymeric lens body having, when hydrated, an equilibrium water content of at least 30%, an oxygen permeability of at least 30 barrers, and a modulus of 0.3 to 1.2 MPa;
- the polymeric lens body comprising a plurality of primary amine functional groups provided by polymerized units of the at least one primary amine-containing methacrylate monomer or the at least one primary amine-containing methacrylamide monomer;
- separating the polymeric lens body from the mold assembly;
- contacting the separated polymeric lens body with an aqueous solution comprising an agent having an attached one or more complementary functional groups, forming covalent bonds between the one or more complementary functional groups of the agent and the plurality of primary amine functional groups of the polymeric lens body, thereby attaching the agent to the contacted polymeric lens body;
- and
- packaging the contacted polymeric lens body in a contact lens packaging solution in a contact lens package to form a finished contact lens.
10 more elements
Dependencies are inferred from the claim text.