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Ultraviolet light absorbing compounds, compositions and methods for making same

Assignee: Allergan Sales LLC
•
Filing: 1988-03-21
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Granted: 1989-07-04
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Expires: 2008-03-21
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Abstract

Abstract An ultraviolet absorbing composition comprising a polymer of at least one diisocyantate, at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet absorbing monomer. Included among the preferred ultraviolet absorbing monomers are compounds which have the following structure: <IMAGE> and mixtures thereof, wherein X is selected from the group consisting of H, alkoxy radicals and halogen; R1 is selected from the group consisting of H and alkyl radicals, provided that at least one of X and R1 is other than H; and R2 is an organic radical including a functional hydroxyl group.

Inventors

  • 👤 Janis C. Henry

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 18:47
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/2805; C08G18/285; C08G18/30; C08G18/38; C08G18/3819; C08G18/3842; C08G18/3851

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 100 words
An ultraviolet absorbing composition comprising a polymer of at least one diisocyanate, at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet light absorbing monomer selected from the group of compounds having the following structure: ##STR4## and mixtures thereof, wherein X is selected from the group consisting of H and alkyl radicals and halogen; R 1 is selected from the group consisting of H and alkyl radical, provided that at least one of X and R 1 is other than H; and R 2 is an organic radical including a functional hydroxyl group, said composition being optically clear.
Claim 2
Dependent Claim 100 words
An ultraviolet absorbing composition comprising a polymer of at least one diisocyanate, at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet light absorbing monomer selected from the group of compounds having the following structure: ##STR4## and mixtures thereof, wherein X is selected from the group consisting of H and alkyl radicals and halogen; R 1 is selected from the group consisting of H and alkyl radical, provided that at least one of X and R 1 is other than H; and R 2 is an organic radical including a functional hydroxyl group, said composition being optically clear.
Claim 3
Dependent Claim 25 words
The composition of claim 1 wherein said composition is effective to absorb ultraviolet light in the range of about 300 nm to about 400 nm.
Claim 4
Dependent Claim 17 words
The composition of claim 1 wherein said ultraviolet light absorbing monomer has a terminal functional hydroxyl group.
Claim 5
Dependent Claim 15 words
The composition of claim 1 wherein R 2 contains 2 to about 10 carbon atoms.
Claim 6
Dependent Claim 10 words
The composition of claim 1 wherein R 2 is aliphatic.
Claim 7
Dependent Claim 12 words
The composition of claim 1 wherein R 2 contains two carbon atoms.
Claim 8
Dependent Claim 23 words
The composition of claim 5 wherein R 2 is --(CH 2 ) m --CH 2 --OH, wherein m is 0 to about 4.
Claim 9
Dependent Claim 24 words
The composition of claim 1 wherein R 1 is selected from the group consisting of alkyl radicals containing 1 to about 8 carbon atoms.
Claim 10
Dependent Claim 24 words
The composition of claim 1 wherein R 1 is selected from the group consisting of t-alkyl radicals containing from 4 to 6 carbon atoms.
Claim 11
Dependent Claim 12 words
The composition of claim 1 wherein R 1 is a t-butyl radical.
Claim 12
Dependent Claim 13 words
The composition of claim 1 wherein said ultraviolet light absorbing monomer is 2-(2-hydroxy-3-t-butyl-5-(2-hydroxyethyl)phenyl)-5-chloro-2H-benzotriazole
Claim 13
Dependent Claim 33 words
The composition of claim 1 wherein said ultraviolet light absorbing monomer is included in said polymer in an amount in the range of about 0.1% to about 10% by weight of said polymer.
Claim 14
Dependent Claim 34 words
The composition of claim 1 wherein said ultraviolet absorbing monomer is included in said polymer in an amount in the range of about 0.1% to less than about 1% by weight of said polymer.
Claim 15
Dependent Claim 39 words
The composition of claim 1 wherein said diisocyanate is selected from the group of aliphatic organic diisocyanates and mixtures thereof; and said polyol is selected from the group consisting of dihydroxyl functional compounds, trihydroxyl functional compounds and mixtures thereof.
Claim 16
Dependent Claim 11 words
The composition of claim 1 which further comprises a cross-linking agent.
Claim 17
Independent Claim 108 words
A method for producing a polymer comprising combining at least one diisocyanate, at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet absorbing monomer at effective polymerization conditions to form an optically clear polymer, said ultraviolet absorbing monomer being selected from the group of compounds having the following structure: ##STR5## and mixtures thereof, wherein X is selected from the group consisting of H, alkoxy radicals and halogen; R 1 is selected from the group consisting of H and alkyl radicals, provided that at least one of X and R 1 is other than H; and R 2 is an organic radical including a functional hydroxyl group.
Claim 18
Independent Claim 108 words
A method for producing a polymer comprising combining at least one diisocyanate, at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet absorbing monomer at effective polymerization conditions to form an optically clear polymer, said ultraviolet absorbing monomer being selected from the group of compounds having the following structure: ##STR5## and mixtures thereof, wherein X is selected from the group consisting of H, alkoxy radicals and halogen; R 1 is selected from the group consisting of H and alkyl radicals, provided that at least one of X and R 1 is other than H; and R 2 is an organic radical including a functional hydroxyl group.
Claim 19
Dependent Claim 16 words
The method of claim 16 wherein said ultraviolet absorbing monomer has a terminal, functional hydroxyl group.
Claim 20
Dependent Claim 10 words
The method of claim 16 wherein R 2 is aliphatic.
Claim 21
Dependent Claim 15 words
The method of claim 16 wherein R 2 contains 2 to about 10 carbon atoms.
Claim 22
Dependent Claim 12 words
The method of claim 16 wherein R 2 contains two carbon atoms.
Claim 23
Dependent Claim 23 words
The method of claim 18 wherein R 2 is --(CH 2 ) m --CH 2 --OH, wherein m is 0 to about 4.
Claim 24
Dependent Claim 12 words
The method of claim 16 wherein said ultraviolet absorbing monomer is 2-(2-hydroxy-3-t-butyl-5-(2-hydroxyethyl)phenyl)-5-chloro-2H-benzotriazole.
Claim 25
Independent Claim 134 words
A method for producing a polymer comprising combining at least one diisocyanate and at least one polyol at effective polymerization condition to produce a relatively low molecular weight polymer; and combining said relatively low molecular weight polymer with at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet absorbing monomer at effective polymerization conditions to form an optically clear polymer, said ultraviolet absorbing monomer being selected from the group of compounds having the following structure: ##STR6## and mixtures thereof, wherein X is selected from the group consisting of H, alkoxy radicals and halogen; R 1 is selected from the group consisting of H and alkyl radicals, provided that at least one of X and R 1 is other than H; and R 2 is an organic radical including a functional hydroxyl group.
Claim 26
Independent Claim 134 words
A method for producing a polymer comprising combining at least one diisocyanate and at least one polyol at effective polymerization condition to produce a relatively low molecular weight polymer; and combining said relatively low molecular weight polymer with at least one polyol and at least one hydroxyl functional, polymerizable ultraviolet absorbing monomer at effective polymerization conditions to form an optically clear polymer, said ultraviolet absorbing monomer being selected from the group of compounds having the following structure: ##STR6## and mixtures thereof, wherein X is selected from the group consisting of H, alkoxy radicals and halogen; R 1 is selected from the group consisting of H and alkyl radicals, provided that at least one of X and R 1 is other than H; and R 2 is an organic radical including a functional hydroxyl group.
Claim 27
Dependent Claim 16 words
The method of claim 23 wherein said ultraviolet absorbing monomer has a terminal, functional hydroxyl group.
Claim 28
Dependent Claim 10 words
The method of claim 23 wherein R 2 is aliphatic.
Claim 29
Dependent Claim 15 words
The method of claim 23 wherein R 2 contains 2 to about 10 carbon atoms.
Claim 30
Dependent Claim 12 words
The method of claim 23 wherein R 2 contains two carbon atoms.
Claim 31
Dependent Claim 29 words
The method of claim 23 wherein the composition of claim 5 wherein R 2 is --(CH 2 ) m --CH 2 --OH, wherein m is 0 to about 4.
Claim 32
Dependent Claim 12 words
The method of claim 23 wherein said ultraviolet absorbing monomer is 2-(2-hydroxy-3-t-butyl-5-(2-hydroxyethyl)phenyl)-5-chloro-2H-benzotriazole.

References Cited (Backward Citations)

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US4021405A Cited
US4179548A Cited
US4131571A Cited
US4096128A Cited
US4383863A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-07-03 1993-01-02 1993-07-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-07-03 1997-01-02 1997-07-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-07-03 2001-01-02 2001-07-04 $7700.00 Window Closed / Lapsed

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