Method for making UV-absorbing ophthalmic lenses

• US 9,315,669 B2
• Filed: 09/23/2014
• Issued: 04/19/2016
• Est. Priority Date: 09/30/2013
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Holland, Troy Vernon, Chang, Frank, Haken, Uwe, Weinschenk, Joseph I. III
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): WHITELEY, JESSICA
• Application Number:
  US14/494,186
• Publication Number:
  US 20150094393A1
• Time in Patent Office: 574 Days
• Field of Search: 522/66, 522/6, 522/71, 522/189, 522/184, 522/1, 520/1
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00913 full body; edge-to-edge
• CPC Class Codes: C08F 2/48 by ultraviolet or visible light
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Described herein is a method for producing UV-absorbing silicone hydrogel contact lenses, which is free or substantially free of internal stress and also is capable of blocking ultra-violet (“UV”) radiation and optionally (but preferably) violet radiation with wavelengths from 381 nm to 440 nm, according to a photocuring technology, preferably according to the Lightstream Technology™. This invention also provides UV-absorbing contact lenses made according to a method of the invention.

Claims

1. A method for producing UV-absorbing silicone hydrogel contact lenses which have an UVB transmittance of about 10% or less between 280 and 315 nanometers, an UVA transmittance of about 30% or less between 316 and 380 nanometers, and an average violet transmittance of about 70% or less between 381 nm and 440 nm, the method comprising the steps of:

(1) providing a mold for making a soft contact lens, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces;

(2) introducing a UV-absorbing pre-polymerization mixture of lens-forming materials into the cavity, wherein the pre-polymerization mixture comprises

(a) at least one hydrophilic vinylic monomer,

(b) at least one siloxane-containing vinylic monomer,

(c) at least one polysiloxane crosslinker with two or more ethylenically-unsaturated groups,

(d) a first UV-absorbing vinylic monomer and a second UV-absorbing vinylic monomer, wherein the first UV-absorbing vinylic monomer absorbs UV radiation and high-energy-violet-light radiation of from 380 nm to 440 nm, wherein the second UV-absorbing vinylic monomer absorbs UV radiation, wherein the first and second vinylic monomers are present in the UV-absorbing pre-polymerization mixture in an amount sufficient to render a contact lens formed from the curing of the UV-absorbing pre-polymerization mixture an ability of blocking at least 90% of UVB light between 280 and 315 nanometers, at least 70% of UVA light between 316 and 380 nanometers, and at least 30% of high-energy violet light between 381 nm and 440 nm,

(e) at least one visibility-tinting agent, and

(f) from about 0.05% to about 1.5% by weight of at least one germanium-based Norrish Type I photoinitiator capable of initiating a free-radical polymerization under irradiation with a light source including a light in the region of about 380 to about 550 nm; and

(3) irradiating the pre-polymerization mixture in the mold with a light in a region of from 380 to 550 nm and crosslinking the lens-forming materials to form an UV-absorbing silicone hydrogel contact lens,

wherein the formed UV-absorbing silicone hydrogel contact lens is substantially free of internal stress and has an UVB transmittance of about 10% or less between 280 and 315 nanometers, an UVA transmittance of about 30% or less between 316 and 380 nanometers, and an average violet transmittance of about 70% or less between 381 nm and 440 nm.

2. The method of claim 1, wherein said at least one visibility-tinting agent comprise a violet-tinting agent.

3. The method of claim 1, wherein the first UV-absorbing vinylic monomer is a benzotriazole-containing UV/HEVL vinylic monomer of formula

4. The method of claim 3, wherein in the formula of the benzotriazole-containing UV/HEVL vinylic monomer, R¹=CH₃;

R²=CH₃O; and

R³=H, CH₃, CH₃O, F, or CF₃.

5. The method of claim 1, wherein the second UV-absorbing vinylic monomer is 2-(2′

-hydroxy-5′

-methacryloxyethylphenyl)-2H-benzotriazole.

6. The method of claim 1, wherein said at least one germanium-based Norrish Type I photoinitiator comprises an acylgermanium compound of formula

7. The method of claim 2, wherein said at least one visibility-tinting agent comprises a blue-tinting agent.

8. The method of claim 1, the pre-polymerization mixture of lens-forming materials of the invention comprises:

(1) from about 10% to about 75% by weight of at least one hydrophilic vinylic monomer;

(2) from about 5% to about 50% by weight of at least one siloxane-containing vinylic monomer;

(3) from about 5% to about 50% by weight of at least one polysiloxane crosslinker;

(4) from about 0.1% to about 4% by weight of the first and second UV-absorbing vinylic monomers; and

(5) from about 0.05% to about 1.5% by weight of at least one germanium-based Norrish Type I photoinitiator, provided that the listed components and any additional components add up to 100% by weight.

9. The method of claim 1, wherein the hydrophilic vinylic monomer is a hydrophilic (meth)acrylamide-type monomer and the siloxane-containing vinylic monomer is a siloxane-containing (meth)acrylamide-type monomer, wherein the pre-polymerization mixture is characterized by having an ability to be cured within about 100 seconds by a visible light having a total intensity of from about 10 to about 100 mW/cm² in the wavelength region from 380 nm to 550 nm.

10. The method of claim 9, wherein the mold is a reusable mold suitable, wherein the step of irradiating is performed under a spatial limitation of actinic radiation, wherein the formed UV-absorbing silicone hydrogel contact lens comprises a lens edge defined by the spatial limitation of actinic radiation.

11. The method of claim 9, wherein the hydrophilic (meth)acrylamide-type monomer is N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-(hydroxymethyl)acrylamide, N-hydroxyethyl acrylamide, N-hydroxypropyl acrylamide, N-[Tris(hydroxymethyl)methyl]acrylamide, acrylamide, methacrylamide, N-(2-aminoethyl)(meth)acrylamide, N-(3-aminopropyl)(meth)acrylamide, or a mixture thereof.

12. The method of claim 11, wherein the siloxane-containing (meth)acrylamide-type monomer is selected from the group consisting of N-[tris(trimethylsiloxy)silylpropyl](meth)acrylamide, N-[tris(dimethylethylsiloxy)-silylpropyl](meth)acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]acrylamide, N-[tris(dimethylphenylsiloxy)silylpropyl](meth)acrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)-2-methyl acrylamide, N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)acrylamide, N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]-2-methyl acrylamide, and N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]acrylamide, N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl)-2-methyl acrylamide, N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl) acrylamide, N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl]-2-methyl acrylamide, N,N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl]acrylamide, N-[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]-2-methyl acrylamide, a siloxane-containing (meth)acrylamide-type monomer of formula (I), a siloxane-containing (meth)acrylamide-type monomer of formula (II), and combinations thereof,

13. The method of claim 12, wherein said at least one polysiloxane crosslinker comprises a polysiloxane crosslinker of formula (III)

14. The method of claim 1, wherein the light source is a light-emitting-device having a peak wavelength of from 410 nm to 480 nm.

15. The method of claim 9, wherein the intensity of the light source is from about 4 to about 80 mW/cm² in the 380 nm to 550 nm region, wherein the pre-polymerization mixture in the mold is irradiated under the spatial limitation of actinic radiation for a time period of about 50 seconds or less.

16. The method of claim 3, wherein the second UV-absorbing vinylic monomer is 2-(2′

-hydroxy-5′

-methacryloxyethylphenyl)-2H-benzotriazole.

17. A UV-absorbing silicone hydrogel contact lens obtained according to a method of claim 1, wherein the contact lens has:

an oxygen permeability of at least about 40 barrers at about 35°

C.;

an elastic modulus of about 2.0 MPa or less at room temperature; and

/or a water content of from about 15% to about 70% at room temperature when fully hydrated.