Method for making UV-absorbing ophthalmic lenses

• US 9,052,439 B2
• Filed: 07/20/2011
• Issued: 06/09/2015
• Est. Priority Date: 07/30/2010
• Status: Expired due to Fees

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Samuel, Newton T., Pruitt, John Dallas, Wu, Daqing, Kuyu, Selma
• Primary Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US13/186,616
• Publication Number:
  US 20120023869A1
• Time in Patent Office: 1,420 Days
• Field of Search: 523/106
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00048 composed of parts with dissimilar composition B29D11/00057 takes precedence
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

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 covalent attachment of a UV-absorbing compound having a second reactive functional group to a preformed contact lens having a first reactive functional group therein and/or thereon.

Claims

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

(1) obtaining a contact lens including a polymer matrix comprising reactive vinylic monomer units each having a first reactive functional group which is azlactone group, epoxy group, isocyanate group, aziridine group, or combination thereof, wherein the contact lens is obtained by polymerizing in a mold a lens formulation comprising a reactive vinylic monomer selected from the group consisting of an azlactone-containing vinylic monomer, an epoxy-containing vinylic monomer, an isocyanate-containing vinylic monomer, an aziridine-containing vinylic monomer, and a combination thereof;

(2) obtaining a solution containing a UV-absorbing compound having a UV-absorbing moiety and an amino group of —

NHR in which R is hydrogen or a C₁-C₂₀ unsubstituted or substituted, linear or branched alkyl group; and

(3) covalently attaching UV-absorbing moieties to the polymer matrix of the contact lens through covalent linkages each formed in a reaction between the amino group of the UV-absorbing compound and one of the first reactive functional groups of the reactive vinylic monomer units of the polymer matrix, by contacting the contact lens with the solution of the UV-absorbing compound.

2. The method of claim 1, wherein the UV-absorbing moieties are benzotriazole-moieties, benzophenone-moieties, or combinations thereof.

3. The method of claim 1, wherein the UV-absorbing compound in step (2) comprises a compound of formula I, II, III, or IV

4. The method of claim 1, wherein the reactive vinylic monomer is present in the lens formulation in an amount of from about 0.05% to about 6.0% by weight, based on the lens formulation.

5. The method according to claim 1, wherein the UV-absorbing compound comprises a compound of formula I, II or III in which Y is amino group of —

NHR in which R is hydrogen or a C₁-C₂₀ unsubstituted or substituted, linear or branched alkyl group, R¹ and R² independent of each other is hydrogen, halogen, C₁-C₆ linear or branched alkoxy, C₁-C₁₂ linear or branched alkyl, or C₆-C₁₅ aryl, L is a covalent bond or a divalent radical of —

X_a-E₁-X_b-E₂-X_c—

in which X_a is a covalent bond or

6. The method of claim 1, wherein the solution of the UV-absorbing compound is prepared by dissolving the UV-absorbing compound in water, a mixture of water and an organic solvent miscible with water, an organic solvent, or a mixture of one or more organic solvent.

7. The method of claim 5, wherein the solution of the UV-absorbing compound is prepared by dissolving the UV-absorbing compound in water, a mixture of water and an organic solvent miscible with water, an organic solvent, or a mixture of one or more organic solvent.

8. The method according to claim 7, wherein the contact lens is subjected to one or more processes selected from the group consisting of lens extraction, hydration, surface treatment, packaging in a lens package contained a packaging solution, sterilization and combinations thereof.

9. The method according to claim 7, wherein the contact lens is a soft contact lens.

10. The method of claim 9, the soft contact lens is a silicone hydrogel contact lens.

11. A contact lens produced according to a method of claim 3.