Ultraviolet light absorbing silicone compositions

• US 4,868,251 A
• Filed: 11/19/1987
• Issued: 09/19/1989
• Est. Priority Date: 12/24/1986
• Status: Expired due to Term

• Current Assignee: Advanced Medical Optics Incorporated (Johnson & Johnson)
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: Reich, Cary J., Christ, F. Richard
• Primary Examiner(s): BRIGGS SR, WILBERT
• Application Number:
  US07/122,945
• Time in Patent Office: 670 Days
• Field of Search: 525/479, 525/281, 525/478, 528/27
• US Class Current: 525/479
• CPC Class Codes: C08G 77/045 containing less than 25 silicon atoms
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

An ultraviolet light absorbing silicone composition comprising silicone elastomer and, covalently bonded thereto, ultraviolet light absorbing component derived from one or more vinyl functional, polymerizable ultraviolet absorbing monomers having the following structures: ##STR1## 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 and R are independently selected from organic radicals with a terminal double bond.

Claims

1. An ultraviolet light absorbing silicone composition comprising silicone base polymer selected from the group consisting of platinum catalyzed vinyl-hydride addition cured polydiorganosiloxanes and mixtures thereof and, covalently bonded thereto, ultraviolet light absorbing component derived from one or more vinyl functional, polymerizable ultraviolet absorbing monomers having the following structure:

##STR8## 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 with a terminal double bond.

2. The composition of claim 1 wherein R₂ is a straight chain or branched chain alkenyl group.

3. The composition of claim 1 wherein the ultraviolet absorbing component is present in an amount effective to absorb ultraviolet light in the range of about 300 to about 400 nm.

4. The composition of claim 1 wherein said silicone base polymer has the formula:

##STR9## wherein R'"'"'₁ is a methyl radical, R'"'"'₂ is selected from the group consisting of alkyl radicals, flouro alkyl radicals, alkenyl radicals with a terminal double bond, aryl radicals, substituted aryl radicals, and mixtures thereof, and n and are integers in the range of 0 to about 500.

5. The composition of claim 1 wherein said silicone base polymer is selected from the group consisting of polydimethylsiloxanes, poly(dimethyl-diphenyl) siloxanes, polyfluoroorganosiloxanes and mixtures thereof.

6. The composition of claim 1 wherein said silicone base polymer is derived from a two part, platinum catalyzed polymerization process.

7. The composition of claim 1 wherein R₂ is selected from the group consisting of a vinyl functionality, an acrylate functionality and a methacrylate functionality.

8. The composition of claim 1 wherein the ultraviolet absorbing monomer is 2-(2-hydroxy-3-t-butyl-5-vinylphenyl)-5-chloro-2H-benzotriazole.

9. The composition of claim 1 wherein the ultraviolet light absorbing component is present in an amount of less than about 1% by weight.

10. The composition of claim 1 which is defined utililizing at least one hydride functional siloxane crosslinking agent.

11. The composition of claim 1 which is optically clear.

12. A corneal contact lens, an intraocular lens or a corneal intrastromal lens comprising the composition of claim 15.

13. The composition of claim 1 wherein R₂ is a vinyl group.

14. The composition of claim 4 wherein said vinyl functional, polymerizable ultraviolet absorbing monomer is 2-(2-hydroxy-3-t-butyl-5-vinylphenyl)-5-chloro-2H-benzotriazole.

15. A corneal contact lens, an intraocular lens or a corneal intrasotromal lens comprising the composition of claim 13.

16. A corneal contact lens, an intraocular lens or a corneal intrastromal lens comprising the composition of claim 14.

17. A corneal contact lens, an intraocular lens or a corneal intrastromal lens comprising the composition of claim 1.