Method for making UV-absorbing ophthalmic lenses

Patent metadata

Field	Value
Publication number	US-9315669-B2
Application number	US-201414494186-A
Country	US
Kind code	B2
Filing date	Sep 23, 2014
Priority date	Sep 30, 2013
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

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.

First claim

What is claimed is:

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

wherein R 1 =H, CH 3 , CH 2 CH 3 , or CH 2 OH; R 2 =C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and R 3 =H, CH 3 , CH 3 O, F, Cl, Br, I, or CF 3 .

4. The method of claim 3 , wherein in the formula of the benzotriazole-containing UV/HEVL vinylic monomer, R 1 =CH 3 ; R 2 =CH 3 O; and R 3 =H, CH 3 , CH 3 O, F, or CF 3 .

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/cm 2 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,

in which R′ is hydrogen or methyl, R″, R 11 and R 12 independent of one another are C 1 -C 6 alkyl, r1 and r2 independent of each other are integer of 0 or 1, m1 is an integer of 3 to 10, R 9 and R 10 independent of each other are a substituted or unsubstituted C 1 -C 10 alkylene divalent group, X 1 is a linkage of

 in which R″ is as defined above and R 12 ″ and R 12 ′ independent of each other are C 1 -C 6 alkyl.

13. The method of claim 12 , whe

Assignees

• Novartis Ag

Inventors

• Holland Troy Vernon
• Chang Frank
• Haken Uwe
• Weinschenk Iii Joseph I

Classifications

• G02B1/043

  Contact lenses · CPC title

• C08F220/54

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C08L83/04 Primary

  Polysiloxanes · CPC title

• C08F230/08

  containing silicon · CPC title