US2001025198A1PendingUtilityA1
UV blocking lenses and material containing benzotriazoles and benzophenones
Est. expiryJul 21, 2018(expired)· nominal 20-yr term from priority
Inventors:Hermann Faubl
G02B 1/043
39
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Claims
Abstract
A contact lens with enhanced UV blocking to meet ANSI Class 1 specifications includes enhanced effective amounts of two different UV absorbing compounds. One UV absorber is a benzotriazole derivative, and the other UV absorber is a benzophenone derivative.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A contact lens comprising a hydrogel polymer formed by polymerizing one or more monomers suitable for use in making such lenses, and incorporating effective amounts of a first ultraviolet absorber and a second ultraviolet absorber, wherein said first UV absorber is a benzotriazole compound represented by the formula:
where R 1a , R 1b , and R 1c are independently hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; R 2 is hydrogen or lower alkyl, aryl or substituted aryl; R 3 is hydrogen, lower alkyl, aryl, substituted aryl, or R 4 -R 5 -R 6 , where R 4 is an oxygen or is absent, R 1 is a linking group selected from —(CH 2 ) n O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) n OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; R 6 is acrylate, methacrylate, styrene or vinyl; and n is 2 or 3; and wherein the second UV absorber is a substituted 2-hydroxy-benzophenone according to the formula:
where R 7a , R 7b , and R 7 c are independently hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; R 8 is a linking group selected from alkyl, —(CH 2 ) m O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) m OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; and R 9 is alkyl, acrylate, methacrylate, styrene or vinyl; and m is 2 or 3.
2 . The lens of claim 1 wherein the first UV absorber is a benzotriazole compound represented by the formula:
where R 1 is hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; and R 5 is a linking group selected from —(CH 2 ) n O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) n OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; and n is 2 or 3.
3 . The lens of claim 2 wherein R 1 is methoxy.
4 . The lens of claim 2 wherein R 5 is —(CH 2 ) n OCH 2 —.
5 . The lens of claim 4 wherein n is 3.
6 . The lens of claim 1 wherein the second UV absorber is 2-hydroxy-4-acryloxyethoxy-benzophenone, 2-hydroxy-4-methacryloxy-benzophenone, or 2-hydroxy-4-methoxy-benzophenone.
7 . The lens of claim 6 wherein the second UV absorbing compound is 2-hydroxy-4-acryloxyethoxy-benzophenone.
8 . The lens of claim 1 wherein the lens has an average UV transmittance of less than 10 percent in the UVA range and an average UV transmittance of less than 1.0 percent in the UVB range.
9 . The lens of claim 8 wherein the average UV transmittance is less than 1.0 percent in the UVA range.
10 . A rigid gas permeable contact lens comprising a polymer formed by incorporating a monomer suitable for use in making such lenses, and effective amounts of a first ultraviolet absorber and a second ultraviolet absorber, wherein said first UV absorber is a benzotriazole compound represented by the formula:
where R 1 is a hydrogen, halogen or lower alkoxy, and R 2 and R 3 are independently hydrogen or lower alkyl; and the second UV absorber is selected from the group consisting of 2-hydroxy4-acryloxyethoxy-benzophenone, 2-hydroxy-4-methacryloxy-benzophenone and 2-hydroxy4-methoxy-benzophenone.
11 . The lens of claim 10 wherein R 2 and R 3 are independently hydrogen, methyl or tert-butyl.
12 . The lens of claim 10 wherein R 2 is tert-butyl.
13 . The lens of claim 10 wherein R 1 is halogen.
14 . The lens of claim 10 wherein the first UV absorber is 2-(2′-hydroxy-3 ′-tert-butyl-5 ′-methylphenyl)-5-chlorobenzotriazole.
15 . The lens of claim 10 wherein the second UV absorber is 2-hydroxy-4-methoxy-benzophenone.
16 . The lens of claim 10 wherein the first UV absorber is 2-(2′-hydroxy-3′-tert-butyl-5′-methylphenyl)-5-chlorobenzotriazole and the second UV absorber is 2-hydroxy4-methoxy-benzophenone.
17 . An intraocular lens comprising a polymer incorporating effective amounts of a first ultraviolet absorber and a second ultraviolet absorber, wherein said first UV absorber is a benzotriazole compound represented by the formula:
where R 1a , R 1b , and R 1c are independently hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; R 2 is hydrogen, lower alkyl, aryl or substituted aryl; R 3 is hydrogen, lower alkyl, aryl, substituted aryl, or R 4 -R 5 -R 6 , where R 4 is an oxygen or is absent, R 5 is a linking group selected from —(CH 2 ) n O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) n OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; R 6 is acrylate, methacrylate, styrene or vinyl; and n is 2 or 3; and wherein the second UV absorber is a substituted 2-hydroxy-benzophenone according to the formula:
where R 7a , R 7b , and R 7c are independently hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; R 8 is a linking group selected from alkyl, —(CH 2 ) m O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) m OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; and R 9 is alkyl, acrylate, methacrylate, styrene or vinyl; and m is 2 or 3.
18 . The lens of claim 17 , wherein the first UV absorber and the second UV absorber are present in a ratio of between about 3:1 and 1:3 by weight.
19 . The lens of claim 17 , wherein the total amount of UV absorbers present is between about 0.8 and about 3.0 percent dry weight of the lens material.
20 . The lens of claim 19 , wherein the total amount of UV absorbers present is between about 1.0 and about 2.0 percent by dry weight of lens material.
21 . The lens of claim 17 , wherein the amount of the first UV absorber present is less than 0.5 percent by dry weight of lens material so as to minimize any observable yellowish tint.
22 . The lens of claim 17 wherein the first UV absorber is a benzotriazole compound represented by the formula:
where R 1 is hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; and R 5 is a linking group selected from —(CH 2 ) n O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) n OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; and n is 2 or 3.
23 . The lens of claim 22 wherein R 1 is methoxy.
24 . The lens of claim 22 wherein R 5 is —(CH 2 ) n OCH 2 —.
25 . The lens of claim 24 wherein n is 3.
26 . A UV-absorbing transparent plastic material incorporating at least two UV absorbing compounds, wherein the first UV absorber is a benzotriazole compound represented by the formula:
where R 1a , R 1b , and R 1c are independently hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; R 2 is hydrogen, lower alkyl, aryl or substituted aryl; R 3 is hydrogen, lower alkyl, aryl, substituted aryl, or R 4 -R 5 -R 6 , where R 4 is an oxygen or is absent, R 5 is a linking group selected from —(CH 2 ) n O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) n OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; R 6 is acrylate, methacrylate, styrene or vinyl; and n is 2 or 3; and wherein the second UV absorber is a substituted 2-hydroxy-benzophenone according to the formula:
where R 7a , R 7b , and R 7c are independently hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; R 8 is a linking group selected from alkyl, —(CH 2 ) m O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) m OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; and R 9 is alkyl, acrylate, methacrylate, styrene or vinyl; and m is 2 or 3.
27 . The plastic material of claim 26 wherein the first UV absorber is a benzotriazole compound represented by the formula:
where R 1 is hydrogen, halogen, C 1 -C 6 straight or branched chain alkoxy group, aryl or substituted aryl; and R 5 is a linking group selected from —(CH 2 ) n O—, —CH(CH 3 )CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) n OCH 2 —, —CH(CH 3 )CH 2 OCH 2 —, or —CH 2 CH(CH 3 )OCH 2 — group, or is absent; and n is 2 or 3.
28 . The plastic material of claim 27 wherein R 1 is methoxy.
29 . The plastic material of claim 27 wherein R 5 is —(CH 2 ) n OCH 2 —.
30 . The plastic material of claim 29 wherein n is 3.
31 . The plastic material of claim 26 wherein the second UV absorber is 2-hydroxy4-acryloxyethoxy-benzophenone, 2-hydroxy-4-methacryloxy-benzophenone, or 2-hydroxy-4-methoxy-benzophenone.
32 . The plastic material of claim 26 wherein the second UV absorbing compound is 2-hydroxy4-acryloxyethoxy-benzophenone.
33 . The plastic material of claim 26 wherein the lens has an average UV transmittance of less than 10 percent in the UVA range and an average UV transmittance of less than 1.0 percent in the UVB range.
34 . The plastic material of claim 33 wherein the average UV transmittance is less than 1.0 percent in the UVA range.Join the waitlist — get patent alerts
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