Polymerizable thioxanthones
US-9278949-B2 · Mar 8, 2016 · US
US12486348B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-12486348-B2 |
| Application number | US-202016938117-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 24, 2020 |
| Priority date | Aug 30, 2019 |
| Publication date | Dec 2, 2025 |
| Grant date | Dec 2, 2025 |
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Described are contact lenses that contain high energy visible (HEV) light absorbing compounds and their use for improving one or more vision attributes.
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We claim: 1 . A contact lens that is a free radical reaction product of a reactive mixture comprising: one or more polymerizable compounds suitable for making the contact lens; and a high energy visible (HEV) light absorbing compound, wherein the contact lens transmits from 0 percent to 70 percent of light across a wavelength range of 400 to 409 nm, wherein the contact lens further comprises a UV absorbing compound that is a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicyclic acid, a benzoic acid, a cinnamic acid, a chalcone, a dypnone, a crotonic acid, or mixtures thereof, and wherein the contact lens provides a greater reduction in halo size for wearers in a 40 to 65 age group than for wearers in an 18-39 age group, when compared to a control lens that does not contain the HEV light absorbing compound. 2 . The contact lens of claim 1 wherein the contact lens transmits 45 percent or less of light across a wavelength range of 280 to 399 nm. 3 . The contact lens of claim 1 that transmits at least 80 percent of light across a wavelength range of 450 to 800 nm. 4 . The contact lens of claim 1 that is photostable. 5 . The contact lens of claim 1 wherein the high energy visible light absorbing compound is a static compound. 6 . The contact lens of claim 1 wherein the high energy visible light absorbing compound comprises a compound of formula I: wherein: m and n are independently 0, 1, 2, 3, or 4; T is a bond, O, or NR; Y is a linking group; P g is a polymerizable group; R at each occurrence is independently H, C 1 -C 6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y—P g ; and R 1 and R 2 , when present, are independently at each occurrence C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkyl, C 3 -C 7 cycloalkyl, aryl, halo, hydroxy, amino, NR 3 R 4 , or benzyl, wherein R 3 and R 4 are independently H or C 1 -C 6 alkyl, or two adjacent R 1 or R 2 groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring. 7 . The contact lens of claim 6 wherein m and n are each independently 0 or 1. 8 . The contact lens of claim 6 wherein Y at each occurrence is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or combinations thereof. 9 . The contact lens of claim 6 wherein P g comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide. 10 . The contact lens of claim 1 wherein the UV absorbing compound comprises a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile or mixtures thereof. 11 . The contact lens of claim 1 wherein the polymerizable compound suitable for making the contact lens comprises a hydrophilic component, a silicone-containing component, or mixtures thereof. 12 . A method for improving a vision attribute in a contact lens wearer, the method comprising: providing the contact lens wearer with a contact lens according to claim 1 , wherein the vision attribute is selected from one or more of photostress recovery time, glare discomfort, glare disability threshold, heterochromatic contrast threshold, halo size, starburst size, and light scattering. 13 . A method for improving a vision attribute in a contact lens wearer, the method comprising: providing the contact lens wearer with a contact lens that is a free radical reaction product of a reactive mixture comprising: one or more polymerizable compounds suitable for making the contact lens; and a high energy visible (HEV) light absorbing compound, a UV absorbing compound that is a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicyclic acid, a benzoic acid, a cinnamic acid, a chalcone, a dypnone, a crotonic acid, or mixtures thereof, wherein the contact lens provides a greater reduction in halo size for wearers in a 40 to 65 age group than for wearers in an 18-39 age group, when compared to a control lens that does not contain the HEV light absorbing compound. 14 . The method of claim 12 wherein improving a vision attribute comprises an improvement in the vision attribute as observed by a contact lens wearer when compared to a contact lens that transmits at least 90 percent of light across the wavelength range of 400 to 409 nm. 15 . The contact lens of claim 1 wherein the HEV light absorbing compound comprises: 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate; 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl acrylate; N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)methacrylamide; N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)acrylamide; 2-(2-cyano-N-methyl-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate; 2-cyano-2-(9H-thioxanthen-9-ylidene)-N-(2-(N-vinylacetamido)ethyl)acetamide; 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)-2-methylpropyl methacrylate; (E)-2-(2-cyano-2-(2,4-dichloro-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate; (E)-2-(2-(2-chloro-9H-thioxanthen-9-ylidene)-2-cyanoacetamido)ethyl methacrylate; (E)-2-(2-cyano-2-(2-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate; (E)-2-(2-cyano-2-(4-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate; 2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetoxy)ethyl methacrylate; or mixtures thereof.
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