Cast-molding process for producing UV-absorbing contact lenses

Patent metadata

Field	Value
Publication number	US-11111327-B2
Application number	US-201916250003-A
Country	US
Kind code	B2
Filing date	Jan 17, 2019
Priority date	Jan 22, 2018
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

Described herein is a cast-molding process for producing contact lenses in a relatively-short curing time from a lens-forming composition, which comprises (a) at least one thiol-containing compound or component, (b) at least one metal scavenger, and (c) at least one free radical scavenger and which has a pH of from about 2.5 to about 5. The addition of a chain-transfer agent into a lens-forming composition can reduce not only the curing time of the lens-forming composition but also reduce the elastic modulus of resultant crosslinked materials (e.g., contact lenses) from the lens-forming composition. The lower pH and the addition of metal scavenger and the free radical scavenger into the lens-forming composition can ensure that the lens-forming composition to have a shelf life of at least three days.

First claim

What is claimed is:

1. A lens-forming composition, comprising:
(a) at least one lens-forming material,
(b) at least one photoinitiator,
(c) at least one thiol-containing compound or polymer in an amount for reducing the curing time of the lens-forming composition, with a light having a wavelength from about 380 to about 460 nm, compared to a control composition which differs from the lens-forming composition only in that the control composition is free of any chain-transfer agent while the lens-forming composition comprises said at least one thiol-containing compound or polymer,
(d) at least one metal ion scavenger,
(e) at least one free radical scavenger, and
(f) optionally at least one polymerizable UV-absorbing component having at least one UV-absorbing moiety which absorbs UV radiation having a wavelength of from 200 nm to 400 nm,
wherein the lens-forming composition has a pH of from about 2.5 to about 5 and a shelf life of at least 3 days.

2. The lens-forming composition of claim 1 , wherein said at least one thiol-containing compound or polymer is selected from the group consisting of 2-mercaptoethylamine, 2-mercaptopropylamine, 3-mercaptopropylamine, 2-mercaptobutylamine, 3-mercaptobutylamine, 4-mercaptobutylamine, 5-mercaptopentylamine, 6-mercaptohexylamine, 1-amino-2-methyl-2-propanethiol hydrochloride, N-methylaminoethanethiol, N-ethylaminoethanethiol, N-methylaminopropanethiol, N-ethylaminopropanethiol, N-methylaminobutanethiol, N-ethylaminobutanethiol, 2-(butylamino)ethanethiol, thioglycolic acid, ammonium thioglycolate, thiolactic acid, mercaptosuccinic acid, meso-2,3-dimercaptosuccinic acid, 2-mercaptoisobutyric acid, 2-methyl-3-sulfanylpropanoic acid, 4-mercaptobutyric acid, 6-mercaptohexanoic acid, 8-mercaptooctanoic acid, 2-mercaptoethanol, 1-mercapto-2-propanol, 2,3-dimercapto-1-propanol, 1-thioglycerol, 3-mercapto-1-propanol, 4-mercapto-1-butanol, 3-mercapto-1-hexanol, 4-mercapto-4-methylpentan-2-ol, 6-mercapto-1-hexanol, 8-mercapto-1-octanol, 9-mercapto-1-nonanol, 2-mercapto-pyrimidine-4,6-diol; cysteine; 4-amino-5-mercapto-pentanoic acid, 2-mercapto-4-amino-6-hydroxypyrimidine, 2-mercapto-succinic acid, 3-mercapto-2-(methylamino)propanoic acid, 2-mercapto-4,5-dihydro-1h-imidazole-4,5-diol, 3-mercaptotyramine, mercaptopropanediol, 2-mercaptomethylglutaric acid, 3-mercapto-DL-valine hydrochloride, 2,2,2-trifluoroethanethiol, ethanethiol, 1,2-ethanedithiol, methyl thioglycolate, 2-methoxyethanethiol, 2-propanethiol, 1,3-propanedithiol, N-acetylcysteamine, cysteamine, L-cysteine-methyl ester-HCl, 2-mercaptoethyl ether, 1-butanethiol, 2-methyl-1-propanethiol, 2-methyl-2-propanethiol, 1,4-butanedithiol, 2,2′-thiodiethanethiol, 4-cyano-1-butanethiol, 3-sulfanyl-2-pentanone, cyclopentanethiol, 2-(2-methoxyethoxy)ethanethiol, 2-methyl-1-butanethiol, 3-methyl-1-butanethiol, 1,5-pentanedithiol, 4-methyl-4-mercaptopentan-2-one, 3-mercapto-3-methyl-1-butyl-1-formate, 3-mercaptobutyl acetate, cyclohexanethiol, 1,6-hexanedithiol, 2-ethylhexanethiol, 1-nonanethiol, trimethylolpropane tris(3-mercaptopropionate), a poly(ethylene glycol) having one sole terminal thiol group, a poly(ethylene glycol) having two terminal thiol groups, a multi-arm poly(ethylene glycol) having one terminal thiol group at each arm, a polyvinyl alcohol having pendant thiol groups, and combinations thereof.

3. The lens-forming composition of claim 1 , wherein said at least one thiol-containing compound or polymer comprises a thiol-containing polyvinyl alcohol which comprises at least about 50% by mole of repeating units of vinyl alcohol; and repeating units of formula (1)

in which: R o and R 3 independent of each other are hydrogen or a C 1 -C 6 alkyl group, R 4 is a C 2 -C 6 alkylene divalent radical, R a is hydrogen or methyl, and R b is hydrogen, C 1 -C 3 alkyl, acetyl, or C 2 -C 4 alkanoylamino which optionally has a carboxyl group.

4. The lens-forming composition of claim 1 , wherein said at least one metal ion scavenger is selected from the group consisting of ethylenediaminetetraacetic acid, diethylenetriamine penta(methylene phosphonic acid) and salts thereof, ethylenediamine tetra(methylene phosphonic acid) and salts thereof, hexamethylenediamine tetra(methylene phosphonic acid) and salts thereof, polyacrylic acid and salts thereof, and combinations thereof.

5. The lens-forming composition of claim 1 , wherein said at least one free radical scavenger is selected from the group consisting of 4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, citric acid and salts thereof, ascorbic acid and salts thereof, and combinations thereof.

6. The lens-forming composition of claim 1 , wherein the lens-forming composition comprises a UV-absorbing vinylic monomer in an amount to obtain the contact lens which has an UVB transmittance of about 10% or less between 280 and 315 nanometers and an UVA transmittance of about 30% or less between 315 and 380 nanometers.

7. The lens-forming composition of claim 1 , wherein the lens-forming composition comprises about 0.1% to about 3.0% by weight of said at least one polymerizable UV-absorbing component related to the amount of all polymerizable components in the lens-forming composition, wherein said at least one polymerizable UV-absorbing component 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-chlorobenzotriazole, 2-(2′-hydroxy-5′-methacryloxypropylphenyl) benzotriazole, 2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 3-(5-fluoro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate, 3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate, 3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate, 2-hydroxy-5-methoxy-3-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 2-hydroxy-5-methyl-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 4-allyl-2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-methoxyphenol, 2-{2′-Hydroxy-3′-tert-5′[3″-(4″-vinylbenzyloxy)propoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1, 1-dimethylethyl)-4-ethenylphenol, 2-[2′-hydroxy-5′-(2-methacryloxyethyl)phenyl)]-2H-benzotriazole, 2-{2′-Hydroxy-3′-tert-butyl-5′-[3′-methacryloyloxypropoxy]phenyl}-2H-benzotriazole, 2-{2′-Hydroxy-3′-tert-butyl-5′-[3′-methacryloyloxypropoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-{2′-Hydroxy-3′-tert-butyl-5′-[3′-methacryloyloxypropoxy]phenyl}-5-chloro-2H-benzotriazole, 2-[2′-Hydroxy-3′-tert-butyl-5′-(3′-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole, 2-(2′-hydroxy-5-methacrylamidophenyl)-5-methoxybenzotriazole, 2-(3-allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(2-Hydroxy-3-methallyl-5-methylphenyl)-2H-benzotriazole, 2-3′-t-butyl-2′-hydroxy-5′-(3″-dimethylvinylsilylpropoxy)-2′-hydroxy-phenyl)-5-methoxybenzotriazole, 2-(2′-hydroxy-5′-methacryloylpropyl-3′-tert-butyl-phenyl)-5-methoxy-2H-benzotriazole, 2-(2′-hydroxy-5′-acryloylpropyl-3′-tert-butyl-phenyl)-5-methoxy-2H-benzotriazole, 2-Methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester, 2-(3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenoxy)ethyl methacrylate, 2-(5-chloro-2H-benzotriazol-2-yl)-6-methoxy-4-(2-propen-1-yl)phenol, 2-[2-Hydroxy

Assignees

• Novartis Ag
• Alcon Inc

Inventors

• Desousa Ryan
• Holland Troy Vernon
• Chang Frank

Classifications

• B29D11/00038 Primary

  Production of contact lenses · CPC title

• G02C7/04

  Contact lenses for the eyes (disinfection or sterilisation of contact lenses A61L12/00) · CPC title

• G02B1/043

  Contact lenses · CPC title

• B29C35/0805

  using electromagnetic radiation · CPC title

• B29D11/00519

  Reusable moulds · CPC title