Method for making UV-absorbing ophthalmic lenses

• US 9,005,700 B2
• Filed: 10/10/2012
• Issued: 04/14/2015
• Est. Priority Date: 10/12/2011
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Bothe, Harald, Qiu, Yongxing, Hagmann, Peter
• Primary Examiner(s): BURKHART, ELIZABETH A
• Application Number:
  US13/648,522
• Publication Number:
  US 20130095235A1
• Time in Patent Office: 916 Days
• Field of Search: 427160-169
• US Class Current: 427/164
• CPC Class Codes: B05D 5/06 to obtain multicolour or other optical effects B05D5/02 takes precedence
• CPC Class Codes: B29D 11/00125 Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
• CPC Class Codes: B29D 11/00634 Production of filters
• 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: G02B 1/043 Contact lenses

Abstract

Described herein is a cost-effective and time-efficient method for making UV-absorbing contact lenses. In contrast to the conventional method for making UV-absorbing contact lenses which involves copolymerizing a lens forming composition including a UV-absorbing vinylic monomer, a method of the invention involves dipping a contact lens in a solution of UV-absorbing polymer comprising carboxyl-containing monomeric units and UV-absorbing monomeric units to form a UV-absorbing coating on the contact lens.

Claims

1. A method for producing UV-absorbing contact lenses, comprising the steps of:

obtaining an ophthalmic lens;

dipping the ophthalmic lens in a coating solution, which comprises a first organic solvent and a UV-absorbing polymer dissolved in the first organic solvent, for a period of time sufficient to form a UV-absorbing coating on the ophthalmic lens, wherein the UV-absorbing polymer comprises UV-absorbing monomeric units and at least 50% by mole of carboxyl-containing monomeric units, wherein the UV-absorbing polymer is obtained by reacting a UV-absorbing compound with a precursor polymer having at least 50% by mole of carboxyl-containing monomeric units in a coupling reaction, wherein the UV-absorbing compound is represented by formula I, II, III, or IV

2. The method of claim 1, wherein the precursor polymer is:

(1) a homopolymer of acrylic acid or C₁-C₁₂ alkylacrylic acid;

(2) a copolymer of acrylic acid and C₁-C₁₂ alkylacrylic acid;

(3) a copolymer of a carboxyl-containing vinylic monomer and an amino-containing vinylic monomer, wherein the carboxyl-containing vinylic monomer is acrylic acid or C₁-C₁₂ alkylacrylic or combination thereof, wherein the amino-containing vinylic monomer is selected from the group consisting of amino-C₂-C₆ alkyl(meth)acrylate, C₁-C₆ alkylamino-C₂-C₆ alkyl(meth)acrylate, allylamine, vinylamine, amino-C₂-C₆ alkyl(meth)acrylamide, C₁-C₆ alkylamino-C₂-C₆ alkyl(meth)acrylamide), and combination thereof;

or (4) a copolymer of a carboxyl-containing vinylic monomer and one or more hydrophilic vinylic monomers, wherein the carboxyl-containing vinylic monomer is acrylic acid or C₁-C₁₂ alkylacrylic or combination thereof, wherein said one or more hydrophilic vinylic monomers are free of carboxyl or amino group and selected from the group consisting of acrylamide (AAm), methacrylamide N,N-dimethylacrylamide (DMA), N,N-dimethyl methacrylamide (DMMA), N-vinylpyrrolidone (NVP), N,N,-dimethylaminoethylmethacrylate (DMAEM), N,N-dimethylaminoethylacrylate (DMAEA), N,N-dimethylaminopropyl methacrylamide (DMAPMAm), N,N-dimethylaminopropylacrylamide (DMAPAAm), 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, C₁-C₄-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 (hydrolyzed form of vinyl acetate in the copolymer), and combinations thereof.

3. The method of claim 1, wherein the precursor polymer is polyacrylic acid, polymethacrylic acid, poly(C₂-C₁₂ alkylacrylic acid), poly(acrylic acid-co-methacrylic acid), poly[C₂-C₁₂ alkylacrylic acid-co-(meth)acrylic acid], poly(N,N-2-acrylamidoglycolic acid), poly[(meth)acrylic acid-co-acrylamide], poly[(meth)acrylic acid-co-vinylpyrrolidone], poly[C₂-C₁₂ alkylacrylic acid-co-acrylamide], poly[C₂-C₁₂ alkylacrylic acid-co-vinyl pyrrolidone], hydrolyzed poly[(meth)acrylic acid-co-vinylacetate], hydrolyzed poly[C₂-C₁₂ alkylacrylic acid-co-vinylacetate], or combinations thereof.

4. The method of claim 1, further comprising a step of rinsing the ophthalmic lens having the UV-absorbing coating thereon with a mixture of water and at most 50% by weight of a second organic solvent, wherein the first organic solvent is present in an amount of at least 60% by weight in the coating solution.

5. The method of claim 4, wherein the method comprises a step of covalently attaching a hydrophilic polymer or polymeric material having reactive functional groups onto the UV-absorbing coating to form a hydrogel coating, wherein the hydrogel coating is covalently attached onto the UV-absorbing coating through linkages each formed between one carboxylic group of the UV-absorbing coating and one reactive functional group of the hydrophilic polymer or polymeric material.

6. The method of claim 5, wherein the reactive functional groups of the hydrophilic polymer and hydrophilic polymeric material are azetidinium groups, epoxy groups, isocyanate groups, aziridine groups, azlactone groups, amino groups, carboxyl groups, and combinations thereof.

7. The method of claim 5, wherein the hydrogel coating is formed by crosslinking a partially-crosslinked polymeric material onto the UV-absorbing coating, wherein the partially-crosslinked polymeric material is water-soluble and comprises a three-dimensional network and reactive functional groups selected from the group consisting of azetidinium groups, epoxy groups, isocyanate groups, aziridine groups, azlactone groups, amino groups, carboxyl groups, and combinations thereof.

8. The method of claim 7, wherein the partially-crosslinked 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, 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 (iii) azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains.

9. The method of claim 8, wherein the step of covalently attaching the hydrophilic polymeric material is performed by autoclaving the contact lens with the UV-absorbing coating thereon in a packaging solution including the partially-crosslinked polymeric material in a sealed lens package at a temperature of from about 118°

C. to about 125°

C. for approximately 20-90 minutes.

10. The method of claim 5, wherein the hydrophilic polymer or hydrophilic polymeric material for forming the hydrogel coating comprises UV-absorbing moieties.

11. The method of claim 5, wherein the UV-absorbing coating further comprises a blue light-absorbing polymer.

12. The method of claim 1, wherein the ophthalmic lens is a silicone hydrogel contact lens which has a surface wettability characterized by having an averaged water contact angle of about 90 degrees or less.

13. A method for producing UV-absorbing contact lenses, comprising the steps of:

obtaining an ophthalmic lens;

dipping the ophthalmic lens in a coating solution, which comprises a first organic solvent and a UV-absorbing polymer dissolved in the first organic solvent, for a period of time sufficient to form a UV-absorbing coating on the ophthalmic lens, wherein the UV-absorbing polymer comprises UV-absorbing monomeric units and at least 50% by mole of carboxyl-containing monomeric units, wherein the first organic solvent is present in an amount of at least 60% by weight in the coating solution;

rinsing the ophthalmic lens having the UV-absorbing coating thereon with a mixture of water and at most 50% by weight of a second organic solvent; and

covalently attaching a hydrophilic polymer or polymeric material having reactive functional groups onto the UV-absorbing coating to form a hydrogel coating, wherein the hydrogel coating is covalently attached onto the UV-absorbing coating through linkages each formed between one carboxylic group of the UV-absorbing coating and one reactive functional group of the hydrophilic polymer or polymeric material.

14. The method of claim 13, wherein each UV-absorbing monomeric unit comprises a benzotriazole or benzophenone moiety.

15. The method of claim 14, wherein the UV-absorbing polymer is obtained by copolymerizing a polymerizable mixture comprising at least one carboxyl-containing vinylic monomer and at least one UV-absorbing vinylic monomer in the presence or absence of a vinylic monomer, provided that the carboxyl-containing vinylic monomer is present in an amount of at least 50% by mole in the polymerizable composition.

16. The method of claim 15, wherein the UV-absorbing vinylic monomer is selected from the group consisting of 2-(2-hydroxy-5-vinylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-acrylyloxyphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-methacrylamido methyl-5-tert octylphenyl) benzotriazole, 2-(2′

-hydroxy-5′

-methacrylamidophenyl)-5-chlorobenzotriazole, 2-(2′

-hydroxy-5′

-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(2′

-hydroxy-5′

-methacryloxypropyl-3′

-t-butyl-phenyl)-5-chlorobenzotriazo le, 2-(2′

-hydroxy-5′

-methacryloxyethylphenyl) benzotriazole, 2-(2′

-hydroxy-5′

-methacryloxypropylphenyl) benzotriazole, 2-hydroxy-4-acryloxy alkoxy benzophenone, 2-hydroxy-4-methacryloxy alkoxy benzophenone, allyl-2-hydroxybenzophenone, and 2-hydroxy-4-methacryloxy benzophenone, and combinations thereof;

wherein the carboxyl-containing vinylic monomer is selected from the group consisting of acrylic acid, C₁-C₁₂ alkylacrylic 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.

17. The method of claim 13, wherein the reactive functional groups of the hydrophilic polymer and hydrophilic polymeric material are azetidinium groups, epoxy groups, isocyanate groups, aziridine groups, azlactone groups, amino groups, carboxyl groups, and combinations thereof.

18. The method of claim 13, wherein the hydrogel coating is formed by crosslinking a partially-crosslinked polymeric material onto the UV-absorbing coating, wherein the partially-crosslinked polymeric material is water-soluble and comprises a three-dimensional network and reactive functional groups selected from the group consisting of azetidinium groups, epoxy groups, isocyanate groups, aziridine groups, azlactone groups, amino groups, carboxyl groups, and combinations thereof.

19. The method of claim 18, wherein the partially-crosslinked 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, 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 (iii) azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains.

20. The method of claim 19, wherein the step of covalently attaching the hydrophilic polymeric material is performed by autoclaving the contact lens with the UV-absorbing coating thereon in a packaging solution including the partially-crosslinked polymeric material in a sealed lens package at a temperature of from about 118°

C. to about 125°

C. for approximately 20-90 minutes.