Contact lens

An ophthalmic lens comprising a polymeric material that has an oxygen permeability of about 45 to about 150 Dk units and a hydrated water content of about 20 to about 55 weight percent, the polymeric material being comprised of a co-polymer of (a) a hydrophilic monomer, (b) a hydrophobic aromatic or aliphatic monomer or a mixture thereof, (c) a tris(siloxy)silyl group-containing monomer, (d) a fluorinated monomer containing about 3 to about 20 fluorine atoms and 4 to about 20 carbon atoms per monomer molecule that is a suffonamido ethyl ester of acrylic acid or methacrylic acid, and (e) an amount of cross-linker sufficient to provide a stress at break value of about 0.003 to about 30 N/mm2, elongation at break of about 25 to about 3000 percent and a modulus value of about 0.001 to about 10 N/mm2.

A polymeric contact lens comprising a co-polymer that is co-polymerization product of (a) a non-ionic hydrophilic monomer, (b) a hydrophobic aromatic monomer in an amount effective to provide said co-polymer with an increased oxygen permeability, (c) a tris(siloxy)silyl group-containing monomer, (d) a fluorinated monomer containing about 3 to about 20 fluorine atoms and 4 to about 20 carbon atoms per monomer molecule in an amount effective to provide said co-polymer with an increased water content at equilibrium hydration and (e) a cross-linking agent, wherein the weight ratio of the tris(siloxy)silyl group-containing monomer to the non-ionic hydrophilic monomer is about 0.3:1 to about 2:1, said lens having an oxygen permeability of greater than about 60 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens comprising a co-polymer that is co-polymerization product of (a) a non-ionic hydrophilic monomer, (b) a hydrophobic aromatic monomer, (c) a tris(siloxy)silyl group-containing monomer, (d) a fluorinated monomer containing about 3 to about 20 fluorine atoms and 4 to about 20 carbon atoms per monomer molecule which is a sulfonamido ethyl ester of acrylic acid or methacrylic acid and (e) a cross-linking agent, wherein the weight ratio of the tris(siloxy)silyl group-containing monomer to the non-ionic hydrophilic monomer is about 0.3:1 to about 2:1, said lens having an oxygen permeability of greater than about 60 Ok units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A polymeric contact lens comprising a co-polymer that is co-polymerization product of (a) a non-ionic hydrophilic monomer containing a methacrylamide, an acrylamide, a methacrylate ester or an acrylate ester group, (b) a hydrophobic styrene-containing monomer, (c) a tris(siloxy)silyl group-containing monomer that is an amide or ester of acrylic acid or methacrylic acid, (d) a fluorinated monomer containing about 3 to about 20 fluorine atoms and 4 to about 20 carbon atoms per monomer molecule that is a sulfonamido ethyl ester of acrylic acid or methacrylic acid and (e) a cross-linking agent, wherein the weight ratio of the tris(siloxy)silyl group-containing monomer to the non-ionic hydrophilic monomer is about 0.7:1 to about 1.4:1, said lens having an oxygen permeability of greater than about 50 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a tris(siloxy)silyl group-containing monomer, (c) a hydrophobic aromatic monomer, (d) a single monomer selected from a monomer group consisting of a polyfluorinated monomer, a cationic monomer, a hydrophobic non-aromatic monomer or a mixture of at least two members selected from the monomer group, wherein said single monomer or mixture is present in an amount effective to provide said contact lens with an increased oxygen permeability and an increased water content at equilibrium hydration and (e) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, and a weight ratio of tris(siloxy)silyl group-containing monomer to the single monomer or mixture of (d) of about 1.5:1 to about 20:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a tris(siloxy)silyl group-containing monomer, (c) a hydrophobic aromatic monomer, (d) a cationic monomer or a mixture of said cationic monomer and a polyfluorinated monomer and/or a hydrophobic non-aromatic monomer, wherein said cationic monomer is an ester of acrylic or methacrylic acid, and (e) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, and a weight ratio of tris(siloxy)silyl group-containing monomer to the cationic monomer or mixture of (d) of about 1.5:1 to about 20:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer that contains a methacrylamide, an acrylamide, a methacrylate ester or an acrylate ester group, (b) a tris(siloxy)silyl group-containing monomer that is an amide or ester of acrylic acid or methacrylic acid, (c) a hydrophobic styrene-containing monomer, (d) a polyfluorinated monomer or a mixture of said polyfluorinated monomer with a cationic monomer and/or a hydrophobic non-aromatic monomer, wherein said polyfluorinated monomer contains about 3 to about 20 fluorine atoms and 4 to about 20 carbon atoms per monomer molecule and is a sulfonamido ethyl ester of acrylic acid or methacrylic acid, wherein said cationic monomer is an ester of acrylic acid or methacrylic acid, wherein said hydrophobic non-aromatic monomer is a C1-C10 aliphatic ester of acrylic acid or methacrylic acid, and (e) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.6:1 to about 2:1, and a weight ratio of tris(siloxy)silyl group-containing monomer to the polyfluorinated monomer or mixture of (d) of about 1.5:1 to about 20:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a cationic monomer, (c) a tris(siloxy)silyl group-containing monomer, (d) a hydrophobic aromatic monomer and (e) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, said lens exhibiting an oxygen permeability of greater than 45 Ok units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a cationic monomer that is an ester of acrylic or methacrylic acid, (c) a tris(siloxy)silyl group-containing monomer that is an amide or ester of acrylic acid or methacrylic acid, (d) a hydrophobic styrene-containing monomer and (e) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophiiic monomer of about 0.3:1 to about 2:1, said lens exhibiting an oxygen permeability of greater than 45 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a poly(dimethylsiloxy)silyl group-containing monomer, (c) a tris(siloxy)silyl group-containing monomer, (d) a hydrophobic styrene-containing monomer in an amount effective to provide said contact lens with increased oxygen permeability, and (e) a cross-linking agent, said monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, and exhibiting a water content on equilibrium hydration of at least 20 weight percent and an oxygen permeability of about 55 to about 150 Dk units.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a poly(dimethylsiloxy)silyl group-containing monomer, (c) a tris(siloxy)silyl group-containing monomer, (d) a single monomer selected from a monomer group consisting of a cationic monomer, a hydrophobic aromatic monomer, a hydrophobic aliphatic monomer, and a polyfluorinated monomer or a mixture of at least two members selected from the monomer group, wherein said single monomer or mixture is present in an amount effective to provide said contact lens with an increased oxygen permeability and an increased water content at equilibrium hydration and (e) a cross-linking agent, said monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, and exhibiting a water content on equilibrium hydration of at least 20 weight percent and an oxygen permeability of about 55 to about 150 Ok units.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a poly(dimethylsiloxy)silyl group-containing monomer, (c) a tris(siloxy)silyl group-containing monomer, (d) a cationic monomer or a mixture of said cationic monomer with at least one of a hydrophobic aromatic monomer a hydrophobic aliphatic monomer, and a polyfluorinated monomer, wherein said cationic monomer is an ester of acrylic or methacrylic acid, and (e) a cross-linking agent, said monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, and exhibiting a water content on equilibrium hydration of at least 20 weight percent and an oxygen permeability of about 55 to about 150 Dk units.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a tris(siloxy)silyl group-containing monomer, (c) a single monomer selected from a monomer group consisting of a polyfluorinated monomer, a cationic monomer, and a hydrophobic non-aromatic monomer, or a mixture of at least two members selected from the monomer group, wherein said single monomer or mixture is present in an amount effective to provide said contact lens with an increased oxygen permeability and an increased water content at equilibrium hydration and (d) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to hydrophilic monomer of about 0.3:1 to about 2:1, and a weight ratio of tris(siloxy)silyl group-containing monomer to a single monomer or monomer mixture of (c) of about 1.5:1 to about 20:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer, (b) a tris(siloxy)silyl group-containing monomer, (c) a cationic monomer or a mixture of said cationic monomer with a polyfluorinated monomer and/or a hydrophobic non-aromatic monomer, wherein said cationic monomer is an ester of acrylic or methacrylic acid, and (d) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to the hydrophilic monomer of about 0.3:1 to about 2:1, and a weight ratio of tris(siloxy)silyl group-containing monomer to a single monomer or monomer mixture of (c) of about 1.5:1 to about 20:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A contact lens that is the co-polymerization product of a monomer mixture comprising (a) a non-ionic hydrophilic monomer that contains a methacrylamide, an acrylamide, a methacrylate ester or an acrylate ester group, (b) a tris(siloxy)silyl group-containing monomer that is an amide or ester of acrylic acid or methacrylic acid, (c) a polyfluorinated monomer or a mixture of said polyfluorinated monomer with a cationic monomer and/or a hydrophobic non-aromatic monomer, wherein said cationic monomer is an ester of acrylic or methacrylic acid, wherein said hydrophobic non-aromatic monomer is a C1-C10 aliphatic ester of acrylic acid or methacrylic acid, wherein said polyfluorinated monomer containing about 3 to about 20 fluorine atoms per monomer molecule is a sulfonamido ethyl ester of acrylic acid or methacrylic acid and (d) a cross-linking agent, the monomer mixture including a weight ratio of tris(siloxy)silyl group-containing monomer to the hydrophilic monomer of about 0.6:1 to about 2:1, and a weight ratio of tris(siloxy)silyl group-containing monomer to the polyfluorinated monomer or mixture of (c) of about 1.5:1 to about 20:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units and a water content at equilibrium hydration of about 35 to about 55 weight percent.

A prolonged wear contact lens that comprises a co-polymer of (a) a non-ionic hydrophilic monomer, (b) a tris(siloxy)silyl group-containing monomer, (c) a cationic monomer, (d) at least one monomer selected from the group consisting of a polyfluorinated monomer, a poly-(dimethylsiloxy)silyl monomer, and a hydrophobic monomer and (e) a cross-linking agent, wherein the weight ratio of the tris(siloxy)silyl group-containing monomer to the hydrophilic monomer is about 0.3:1 to about 2:1, said lens exhibiting an oxygen permeability of about 45 to about 150 Dk units, a water content at equilibrium hydration of about 35 to about 55 weight percent, said lens separately binding mucin and lysozyme in vitro at a ratio by weight of about 1:2 to about 2:1 and in an amount of about 0.75 to about 2.5 μg/cm2 when said proteins are separately present a initial concentrations of 0.46 g/L in aqueous buffers at a pH value of 7.2-7.6.

A process for preparing an ophthalmic contact lens that comprises the steps of a) thermally co-polymerizing a monomer mixture in a filled and closed casting cup for a time period of about ten to about fifteen minutes at a temperature of about 110 to about 14000, said monomer mixture comprising (a) a hydrophilic monomer that is an unsubstituted, mono- or di-substituted 01-04-alkyl acrylamide or methacrylamide, (b) a tris(siloxy)silyl group-containing monomer, (c) at least one monomer selected from the group consisting of a polyfluorinated monomer, a cationic monomer, a hydrophobic non-aromatic monomer, a hydrophobic aromatic monomer, and a poly(dimethylsiloxy)silyl group-containing monomer and (d) a cross-linking agent, wherein the weight ratio of the tris(siloxy)silyl group-containing monomer to the hydrophilic monomer is about 0.3:1 to about 2:1;

• and (b) on completion of the polymerization, cooling, opening the casting cups, removing the lenses and hydrating the lenses for use, said lens exhibiting an oxygen permeability of about 45 to about 150 Ok units and a hydrated water content of about 20 to about 55 weight percent upon hydration.

In a process of forming ophthalmic lenses by co-polymerization of a monomer mixture comprising (a) a non-ionic hydrophilic monomer that is a methacrylamide or acrylamide, (b) a tris(siloxy)silyl group-containing monomer, the improvement that comprises wet casting said lenses from a composition that includes said monomers, a hydrophobic aromatic or aliphatic monomer or a mixture thereof in an amount effective to provide said lenses with an increased oxygen permeability, a C4-C20 monomer containing about 3 to about 20 fluorine atoms in an amount effective to provide said lenses with an increased water content at equilibrium hydration, and a non-co-polymerizable solvent that is miscible in the monomer mixture and is readily removable from the co-polymerized lens.