Soft contact lenses with a lubricious coating covalently-attached thereon

Patent metadata

Field	Value
Publication number	US-2018113236-A1
Application number	US-201715792806-A
Country	US
Kind code	A1
Filing date	Oct 25, 2017
Priority date	Oct 26, 2016
Publication date	Apr 26, 2018
Grant date	—

Abstract

The invention is generally related to soft contact lenses which comprise a polyvinylalcohol-based hydrogel lens body and a durable lubricious coating thereon which are covalently attached to the polyvinylalcohol-based hydrogel lens body through 6-membered acetal rings and to a method for producing the same.

First claim

What is claimed is:

1 . A method for producing soft contact lenses, comprising the steps of:
(1) obtaining a preformed polyvinylalcohol-based hydrogel contact lens, wherein the preformed polyvinylalcohol-based hydrogel contact lens is composed of a polymer comprising at least 50% by mole of repeating units of vinyl alcohol; (2) contacting the preformed polyvinylalcohol-based hydrogel contact lens with a first aqueous coating solution of a hydrophilic polymer having reactive groups of

in which R 1 is methyl or ethyl and R 2 is hydrogen or a C 1 -C 4 alkyl, at a pH of about 4.0 or less for a contacting time to covalently attach a layer of the hydrophilic polymer onto the preformed polyvinylalcohol-based hydrogel contact lens through 6-membered acetal rings.

2 . The method of claim 1 , wherein the contacting time is about 30 minutes or less, wherein the first aqueous coating solution has a temperature of from about 35° C. to about 85° C. (preferably from about 40° C. to about 80° C., more preferably from about 45° C. to about 70° C.).

3 . The method of claim 2 , wherein the hydrophilic polymer are a linear or branched polymer comprising about 25% or less by mole of repeating units of a vinylic monomer having a reactive group of

4 . The method of claim 4 , wherein the hydrophilic polymer further comprises repeating units of one or more vinylic monomers selected from the group consisting of a carboxyl-containing vinylic monomer, a primary amine-containing vinylic monomer, a secondary amine-containing vinylic monomer, a non-reactive hydrophilic vinylic monomer, a phosphorylcholine-containing vinylic monomer, and combinations thereof.

5 . The method of claim 4 , wherein the carboxyl-containing vinylic monomer is selected from the group consisting of acrylic acid, methacrylic ethylacrylic acid, propylacrylic acid, butylacrylic acid, N,N-2-acrylamidoglycolic acid, beta methyl-acrylic acid (crotonic 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 primary and secondary amine-containing vinylic monomers are amino-C 2 -C 6 alkyl (meth)acrylate, C 1 -C 6 alkylamino-C 2 -C 6 alkyl (meth)acrylate, allylamine, vinylamine, amino-C 2 -C 6 alkyl (meth)acrylamide, C 1 -C 6 alkylamino-C 2 -C 6 alkyl (meth)acrylamide, or a combination thereof, wherein the non-reactive hydrophilic vinylic monomer is (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone (NVP), N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide, N-2-hydroxylethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)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, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500 Daltons, allyl alcohol, vinyl alcohol, or a combination thereof.

6 . The method of claim 4 , wherein the hydrophilic polymer comprises repeating units of one or more vinylic monomers selected from the group consisting of a phosphorylcholine-containing vinylic monomer, (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone (NVP), N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide, N-2-hydroxylethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)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, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500 Daltons, allyl alcohol, vinyl alcohol, or a combination thereof.

7 . The method of claim 4 , wherein the hydrophilic polymer comprises repeating units of one or more carboxyl-containing vinylic monomers selected from the group consisting of acrylic acid, methacrylic acid, ethylacrylic acid, and combinations thereof.

8 . The method of claim 4 , wherein the hydrophilic polymer comprises repeating units of one or more vinylic monomers selected from the group consisting of amino-C 2 -C 3 alkyl (meth)acrylate, C 1 -C 2 alkylamino-C 2 -C 3 alkyl (meth)acrylate, amino-C 2 -C 3 alkyl (meth)acrylamide, C 1 -C 2 alkylamino-C 2 -C 3 alkyl (meth)acrylamide, and combinations thereof.

9 . The method of claim 4 , wherein the method further comprises a step of heating the preformed polyvinylalcohol-based hydrogel contact lens having the layer (or coating) of the hydrophilic polymer thereon in a second aqueous coating solution comprising a water-soluble thermally-crosslinkable polymeric material having azetidinium groups to a temperature of from about 60° C. to about 125° C. and maintaining at the temperature for a time period to form a hydrogel layer (or coating) on top of the layer (or coating) of the hydrophilic polymer.

10 . The method of claim 9 , wherein the step of heating is performed by autoclaving the soft contact lens precursor immersed in the second aqueous coating solution in a sealed lens package at a temperature of from about 115° C. to about 125° C. for approximately 20-90 minutes, wherein the second aqueous coating solution is a buffered aqueous solution with a pH of from 6.7 to 7.6.

11 . The method of claim 10 , wherein the water-soluble thermally-crosslinkable polymeric material comprises (i) from about 20% to about 95% by weight of first polymer chains derived from a polyamidoamine-epichlorohydrin and/or a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin, (ii) from about 5% to about 80% by weight of hydrophilic moieties and/or second polymer chains, wherein each of the hydrophilic moieties is derived from at least one first 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, wherein the hydrophilic moieties are covalently attached to the first polymer chains through one or more covalent linkages each formed between one azetitdinium group and one amino, carboxyl or thiol group of the first hydrophilicity-enhancing agent, wherein each of the second polymer chains is derived from at least one second 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, wherein the second polymer chains are covalently attached to the first p

Assignees

• Novartis Ag

Inventors

• Bothe Harald
• Seiferling Bernhard
• Arndt Heike
• Wasse Thomas
• Wittmar Stephan

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• C07H3/04

  Disaccharides · CPC title

• C08F226/06

  by a heterocyclic ring containing nitrogen · CPC title

• C08L29/04

  Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids · CPC title

• C08F216/38

  by an acetal or ketal radical · CPC title