Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles

• US 4,528,311 A
• Filed: 07/11/1983
• Issued: 07/09/1985
• Est. Priority Date: 07/11/1983
• Status: Expired due to Term

• Current Assignee: Iolab Corp. (Johnson & Johnson)
• Original Assignee: Iolab Corp. (Johnson & Johnson)
• Inventors: Yamada, Akira, Beard, Charles D., Doddi, Namassivaya
• Primary Examiner(s): LEE, LESTER
• Application Number:
  US06/512,860
• Time in Patent Office: 729 Days
• Field of Search: 524/91, 525/204, 526/259, 548/259, 548/261, 351/160 H
• US Class Current: 524/91
• CPC Class Codes: C08F 20/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08K 5/3475 condensed with carbocyclic rings
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Ultraviolet light absorbing polymer compositions comprising copolymers of 2-Hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles with one or more other monomers copolymerizable therewith, particularly acrylic monomers are useful in the manufacture of occular devices, particularly intraoccular lenses and contact lenses. Polymers of the disclosed benzotriazoles may be added to other organic materials to impart ultraviolet absorbing properties thereo.

Claims

1. A compound of the formula ##STR9## wherein X is H or halogen,

R₁ is selected from the group consisting of H, CH₃ and t-alkyl of 4 to 6 carbons,

R₂ is C₂ -C₁₀ alkylene which may be straight chain or branched, and

R₃ is H or CH₃ ;

and

homopolymers thereof.

2. The compound of claim 1 wherein X is chlorine.

3. The compound of claim 1 wherein R₃ is CH₃.

10. An ultraviolet absorbing composition comprising a copolymer of an ethylenically unsaturated monomer and an effective amount of a compound of claim 1.

11. The composition of claim 10 wherein said ethylenically unsaturated material is selected from the group consisting of styrene, methylstyrene, acrylates, methylacrylates, acrylamide, acrylonitrile, methacrylonitrile, vinylacetate, vinylidene chloride, vinyl chloride, ethylene, propylene, and mixtures thereof.

12. The composition of claim 10 wherein said compound of claim 1 is 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropyl-3'"'"'-tertbutylphenyl)-5-chloro-2H-benzotriazole and comprises from 0.05 to 20% by weight of said composition.

13. The composition of claim 12 wherein said UV absorbing composition comprises a copolymer of methyl methacrylate and from 0.05 to 5.0% by weight of said compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropyl-3'"'"'-tertbutylphenyl)-5-chloro-2H-benzotriazole.

14. A composition comprising an organic polymer and as an ultraviolet absorbing additive thereto, from 0.05 to 20 percent by weight of a compound of claim 1.

15. The composition of claim 14 wherein said polymeric material is selected from the group consisting of polyvinyl halides, polyacrylates, polystyrene, polyvinylidene halides, polycarbonates and acrylonitrile-butadiene styrene terpolymers.

16. The composition of claim 15 wherein said compound of claim 1 is a homopolymer of compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropyl-3'"'"'-tert-butylphenyl)-5-chloro-2H-benzotriazole.

17. The composition of claim 16 wherein said homopolymer of compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropyl-3'"'"'-tert-butylphenyl)-5-chloro-2H-benzotriazole is present in an amount of from 0.05 to 5% by weight.

18. A contact lens comprising an optically clear polymer composition of claim 10.

19. A contact lens comprising an optically clear polymer composition of claim 13.

20. An intraoccular lens comprising an optically clear polymer composition of claim 10.

21. An intraoccular lens comprising an optically clear polymer composition of claim 13.

22. A plastic film comprising the composition of claim 10.

23. A plastic film comprising the composition of claim 14.

4. The compound 2-(2'"'"'-Hydroxy-5'"'"'-methacryloxyethylphenyl)-2H-benzotriazole and homopolymers thereof.

5. The compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxyethylphenyl)-5-chloro-2H-benzotriazole and homopolymers thereof.

6. The compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropylphenyl)-2H-benzotriazole and homopolymers thereof.

7. The compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropylphenyl)-5-chloro-2H-benzotriazole and homopolymers thereof.

8. The compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropyl-3'"'"'-tert-butylphenyl)-2H-benzotriazole and homopolymers thereof.

9. The compound 2-(2'"'"'-Hydroxy-5'"'"'-methacrylyloxypropyl-3'"'"'-tert-butylphenyl)-5-chloro-2H-benzotriazole and homopolymers thereof.