Silicone hydrogel lens with a crosslinked hydrophilic coating

• US 9,708,087 B2
• Filed: 12/16/2014
• Issued: 07/18/2017
• Est. Priority Date: 12/17/2013
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Qiu, Yongxing
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/571,851
• Publication Number:
  US 20150166205A1
• Time in Patent Office: 945 Days
• Field of Search: 523107, 35115933
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• CPC Class Codes: B65B 31/00 Packaging articles or materials under special atmospheric or gaseous conditions; Adding propellants to aerosol containers
• CPC Class Codes: B65B 7/16 Closing semi-rigid or rigid containers or receptacles not deformed by, or not taking-up shape of, contents, e.g. boxes or cartons
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02B 1/14 Protective coatings, e.g. hard coatings
• CPC Class Codes: G02B 2207/109 Sols, gels, sol-gel materials

Abstract

The present invention generally relates to a cost-effective and time-efficient method for applying a crosslinked hydrophilic coating onto a silicone hydrogel contact lens to reduce its positively charged preservatives such as PHMB uptake and to improve its hydrophilicity and lubricity.

Claims

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 immersed in a packaging solution comprising the hydrophilic polymeric material and 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 (mOsm) and a viscosity of from about 1 centipoise to about 20 centipoises at 25°

C. in a lens package 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,

(c) adding a polyazetidinium groups-containing component into the package solution with the silicone contact lens of the step (b), wherein the polyazetidinium groups-containing component comprise at least two groups selected from the group consisting of Formula (II), Formula (III) and mixtures thereof;

2. The method of claim 1, wherein the polyazetidinium groups-containing component has a solution viscosity range from 10 to 200 m·

Pa·

s. at 23% solid.

3. The method of claim 2, wherein the polyazetidinium groups-containing component has a solution a viscosity range from 30 to 160 m·

Pa·

s. at 23% solid.

4. The method of claim 3, wherein the polyazetidinium groups-containing component has a solution a viscosity range from 40 to 130 m·

Pa·

s. at 23% solid.

5. The method of claim 1, wherein the in-packaging-coating solution of step (b) comprises from 0.01% to 2% by weight of thermally-crosslinkable hydrophilic polymeric material.

6. The method of claim 1, wherein the polyazetidinium groups-containing component is added in the in-packaging-coating solution of step (c) in an amount of from about 0.01% to about 5% by weight based on the total amount of the in-packaging-coating solution.

7. The method of claim 1, wherein the step of heating is perform by heating the silicone hydrogel contact lens immersed in a packaging solution in a sealed lens package at a temperature from about 40°

C. to about 140°

C. for approximately 20-180 minutes and the step of reducing the concentration of amino groups and/or carboxyl groups on and/or near the silicone hydrogel contact lens by autoclaving the package with the contact lens and the in-package-coating solution at a temperature of from about 118°

C. to about 125°

C. for approximately 20-90 minutes.

8. The method of claim 7, wherein the step of heating is perform by heating the silicone hydrogel contact lens immersed in a packaging solution in a sealed lens package at a temperature from about 75°

C. to about 95°

C. for approximately 20-180 minutes and the step of reducing the concentration of amino groups and/or carboxyl groups on and/or near the silicone hydrogel contact lens by autoclaving the package with the contact lens and the in-package-coating solution at a temperature of from about 118°

C. to about 125°

C. for approximately about 118°

C. to about 125°

C. for approximately 20-40 minutes.

9. The method of claim 1, wherein the hydrophilicity-enhancing agent is a hydrophilic polymers having one or more amino, carboxyl and/or thiol groups, wherein the content of monomeric units having an amino, carboxyl or thiol group in the hydrophilic polymer as the hydrophilicity-enhancing agent is less than about 40% by weight based on the total weight of the hydrophilic polymer.

10. The method of claim 1, wherein the weight average molecular weight Mw of the hydrophilic polymer having at least one amino, carboxyl or thiol group from about 500 to about 1,000,000 Daltons.

11. The method of claim 1, wherein the silicone hydrogel contact lens comprises a reactive base coating including amino and/or carboxyl groups.

12. The method of claim 11, wherein the reactive base coating comprises at least one layer of a reactive polymer having pendant amino groups and/or carboxyl groups and is obtained by contacting the silicone hydrogel contact lens with a solution of the reactive polymer, wherein the reactive polymer is:

a homopolymer of amino-C₁ to C₄ alkyl (meth)acrylamide, amino-C₁ to C₄ alkyl (meth)acrylate, C₁ to C₄ alkylamino-C₁ to C₄ alkyl (meth)acrylamide, C₁ to C₄ alkylamino-C₁ to C₄ alkyl (meth)acrylate, allylamine, or vinylamine;

polyethyleneimine;

a polyvinylalcohol with pendant amino groups;

a linear or branched polyacrylic acid;

a homopolymer of C₁ to C₁₂ alkylacrylic acid;

a copolymer of amino-C₂ to C₄ alkyl (meth)acrylamide, amino-C₂ to C₄ alkyl (meth)acrylate, C₁ to C₄ alkylamino-C₂ to C₄ alkyl (meth)acrylamide, C₁ to C₄ alkylamino-C₂ to C₄ alkyl (meth)acrylate, acrylic acid, C₁ to C₁₂ alkylacrylic acid, maleic acid, and/or fumaric acid, with at least one non-reactive hydrophilic vinylic monomer;

a carboxyl-containing cellulose;

hyaluronate;

chondroitin sulfate;

poly(glutamic acid);

poly(aspartic acid);

or combinations thereof.

13. The method of claim 12, wherein the reactive polymer for forming a base coating is polyacrylic acid, polymethacrylic acid, poly(N,N-2-acrylamidoglycolic acid), poly[(meth)acrylic acid-co-acrylamide], poly[(meth)acrylic acid-co-vinylpyrrolidone], hydrolyzed poly[(meth)acrylic acid-co-vinylacetate], polyethyleneimine (PEI), polyallylamine hydrochloride (PAH) homo- or copolymer, polyvinylamine homo- or copolymer, or combinations thereof.

14. The method of claim 13, wherein the weight average molecular weight Mw of a reactive polymer for forming a reactive base coating is at least about 10,000 Daltons.

15. The method of claim 14, wherein the weight average molecular weight Mw of a reactive polymer for forming a reactive base coating is from about 10,000 to 1,000,000 Daltons.

16. The method of claim 13, wherein the reactive polymer is dissolved in a mixture of water and one or more organic solvents, an organic solvent, or a mixture of one or more organic solvents.