METHOD FOR MAKING UV-ABSORBING OPHTHALMIC LENSES

• US 20120023869A1
• Filed: 07/20/2011
• Published: 02/02/2012
• Est. Priority Date: 07/30/2010
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Samuel, Newton T., Pruitt, John Dallas, Wu, Daqing, Kuyu, Selma
• Granted Patent: US 9,052,439 B2
• Time in Patent Office: Days
• US Class Current: 53/425
• 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; and

(2) covalently attaching UV-absorbing moieties to the polymer matrix through the first reactive functional groups of the reactive vinylic monomer units, by contacting the contact lens with a solution containing a UV-absorbing compound having a UV-absorbing moiety and a second reactive functional group coreactive with the first reactive functional group to form a covalent linkage, wherein one of the first and second reactive functional groups is an azlactone group, an isocyanate group, an epoxy group, an aziridine group, or combination thereof, while the other group is an amino group or a thiol group or both.

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 according to claim 3, wherein the first functional reactive groups are selected from the group consisting of azlactone groups, epoxy groups, isocyanate groups, aziridine groups, and combinations thereof.

5. The method according to claim 4, 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.

6. The method of claim 5, 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.

7. The method of claim 6, wherein the polymer matrix of the contact lens comprises azlactone, epoxy, isocyanate, or aziridine groups or combination thereof, wherein the UV-absorbing compound comprises one or more compounds of formula I, II, III or IV, in which Y and Y¹ is an amino group of —

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

8. The method of claim 7, wherein the UV-absorbing compound comprises a compound of formula I, II or III in which Y is amino group of —

NHR (R is defined above), 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

9. The method according to claim 7, 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.

10. The method of claim 8, 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.

11. The method according to claim 10, 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.

12. The method according to claim 10, wherein the contact lens is a soft contact lens.

13. The method of claim 12, the soft contact lens is a silicone hydrogel contact lens.

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