Silicone hydrogel lens with a crosslinked hydrophilic coating

Patent metadata

Field	Value
Publication number	US-2017037276-A1
Application number	US-201615298298-A
Country	US
Kind code	A1
Filing date	Oct 20, 2016
Priority date	Jul 30, 2010
Publication date	Feb 9, 2017
Grant date	—

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.

First claim

1 - 20 . (canceled)

21 . A contact lens packaging solution, which is an aqueous solution comprising at least one buffering agent in an amount sufficient to maintain a pH of from about 6.0 to about 8.5 and from about 0.01% to about 2% by weight of a water-soluble and thermally-crosslinkable hydrophilic polymeric material;
wherein the water-soluble and thermally-crosslinkable hydrophilic polymeric material which 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, wherein the packaging solution has a tonicity of from about 200 to about 450 milliosmol (mOsm) and a viscosity of from about 1 centipoise to about 20 centipoises at 25° C.

22 . The contact lens packaging solution of claim 21 , wherein the hydrophilicity-enhancing agent is: a polyethylene glycol having one sole amino, carboxyl or thiol group; a polyethylene glycol with two terminal amino, carboxyl and/or thiol groups; a multi-arm polyethylene glycol with one or more amino, carboxyl and/or thiol groups; a polyethylene glycol dendrimer with one or more amino, carboxyl and/or thiol groups.

23 . The contact lens packaging solution of claim 21 , wherein the weight average molecular weight M w of the hydrophilic polymer as the hydrophilicity-enhancing agent is from about 500 to about 1,000,000.

24 . The contact lens packaging solution of claim 21 , wherein the hydrophilic polymer as the hydrophilicity-enhancing agent is a copolymer which is a polymerization product of a composition comprising (1) about 60% or less by weight of at least one reactive vinylic monomer and (2) at least one non-reactive hydrophilic vinylic monomer;
wherein the reactive vinylic monomer is 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, 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; wherein the non-reactive hydrophilic vinylic monomer is selected from the group consisting of acrylamide, methacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-vinylpyrrolidone, N,N,-dimethylaminoethylmethacrylate, N,N-dimethylaminoethylacrylate, N,N-dimethylaminopropylmethacrylamide, N,N-dimethylaminopropylacrylamide, glycerol methacrylate, 3-acryloylamino-1-propanol, N-hydroxyethyl acrylamide, N-[tris(hydroxymethyl)methyl]-acrylamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500 Daltons, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, allyl alcohol, vinyl alcohol, and combinations thereof.

25 . The contact lens packaging solution of claim 24 , wherein said one or more reactive vinylic monomers are vinylic monomers having a carboxyl group.

26 . The contact lens packaging solution of claim 25 , 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.

27 . The contact lens packaging solution of claim 24 , wherein said one or more reactive vinylic monomers are vinylic monomers having an amino group.

28 . The contact lens packaging solution of claim 25 , 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.

29 . The contact lens packaging solution of claim 21 , wherein the hydrophilic polymer as the hydrophilicity-enhancing agent is a copolymer which is a polymerization product of a composition comprising (1) about 60% or less by weight of at least one reactive vinylic monomer and (2) at least one phosphorylcholine-containing vinylic monomer; or combinations thereof,
wherein the reactive vinylic monomer is 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, 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.

30 . The contact lens packaging solution of claim 29 , wherein said one or more reactive vinylic monomers are vinylic monomers having a carboxyl group.

31 . The contact lens packaging solution of claim 30 , 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.

32 . The contact lens packaging solution of claim 29 , wherein said one or more reactive vinylic monomers are vinylic monomers having an amino group.

33 . The contact lens packaging solution of claim 32 , 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.

34 . The contact lens packaging solution of claim 21 , wherein the hydrophilic polymer as the hydrophilicity-enhancing agent is a monoamino-, monocarboxyl-, diamino- or dicarboxyl-terminated homo- or copolymer of a non-reactive hydrophilic vinylic monomer selected from the group consisting of acrylamide, N,N-dimethylacrylamide, N-vinylpyrrolidone, N-vinyl-N-methyl acetamide, glycerol (meth)acrylate, hydroxyethyl (meth)acrylate, N-hydroxyethyl (meth)acrylamide, (meth)acryloyloxyethyl phosphorylcholine, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 400 Daltons, vinyl alcohol, N-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (metha)crylamide, and combination thereof.

35 . The contact lens packaging solution of claim 21 , wherein the hydrophilic

Assignees

• Novartis Ag

Inventors

• Qiu Yongxing
• Samuel Newton T
• Pruitt John Dallas
• Kolluru Chandana
• Medina Arturo Norberto
• Winterton Lynn Cook
• Wu Daqing
• Qian Xinming
• Nelson Jared

Classifications

• G02C7/04

  Contact lenses for the eyes (disinfection or sterilisation of contact lenses A61L12/00) · CPC title

• B29D11/00067 Primary

  Hydrating contact lenses · CPC title

• G02B1/10

  Optical coatings produced by application to, or surface treatment of, optical elements (G02B1/08 takes precedence) · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• G02B1/18

  Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films (G02B1/16 takes precedence) · CPC title