Ultraviolet light absorbing compounds and silicone compositions

• US 5,164,462 A
• Filed: 04/25/1991
• Issued: 11/17/1992
• Est. Priority Date: 04/25/1991
• Status: Expired due to Fees

• Current Assignee: Abbott Medical Optics Incorporated (Johnson & Johnson)
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: Yang, Shih-Liang S.
• Primary Examiner(s): Hoke, Veronica P.
• Application Number:
  US07/691,149
• Time in Patent Office: 572 Days
• Field of Search: 526/259, 523/107, 523/108, 351/160 R, 351/163, 524/91, 548/110, 525/477, 525/478
• US Class Current: 525/478
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C07F 7/0896 Compounds with a Si-H linkage
• CPC Class Codes: C08F 299/08 from polysiloxanes
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08G 77/045 containing less than 25 silicon atoms
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/18 to alkoxy or aryloxy groups
• 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: C08K 5/5477 containing nitrogen in a heterocyclic ring
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• 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 base polymer and ultraviolet light absorbing component present as, or derived from, one or more ultraviolet light absorbing compounds having the following structure: ##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; R² is selected from the group consisting of divalent hydrocarbon radicals, divalent substituted hydrocarbon radicals, oxo, divalent oxyhydrocarbon radicals and divalent substituted oxyhydrocarbon radicals; each R³ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, aryl radicals, substituted aryl radicals and fluoro radical; R is selected from R³, H and CH═CH₂, and c is an integer in the range of 1 to about 20.

Claims

1. An ultraviolet light absorbing silicone composition comprising silicone elastomer and an effective amount of ultraviolet light absorbing component covalently bonded to said silicone elastomer and derived from one or more ultraviolet light absorbing compounds selected from the group consisting of compounds having the following structure ##STR9## 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;

R² is selected from the group consisting of divalent hydrocarbon radicals, divalent substituted hydrocarbon radicals, oxo, divalent oxyhydrocarbon radicals and divalent substituted oxyhydrocarbon radicals;

each R³ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, aryl radicals, substituted aryl radicals and fluoro radical;

R is selected from the group consisting of H and CH=CH₂ ; and

c is an integer in the range of 1 to about 20.

2. The composition of claim 1 wherein each R³ is independently selected from the group consisting of alkyl radicals and aryl radicals.

3. The composition of claim 1 wherein R¹ is selected from alkyl radicals.

4. The composition of claim 1 wherein said compounds have the following structure:

##STR10##

5. The composition of claim 1 wherein said silicone elastomer is a vinyl/hydride addition cured polysiloxane.

6. The composition of claim 1 wherein each R3 is independently selected from the group consisting of alkyl radicals having 1 to about 4 carbon atoms, substituted alkyl radicals having 1 to about 4 carbon atoms, alkoxy radicals having 1 to about 4 carbon atoms, substituted alkoxy radicals having 1 to about 4 carbon atoms, phenyl radicals and substituted phenyl radicals.

7. The composition of claim 1 wherein each R³ is a methyl radical and c is an integer in the range of 1 to about 4.

8. The composition of claim 1 wherein R² is selected from the group consisting of methylene, substituted methylene, ethylene, substituted ethylene, oxo, divalent oxyhydrocarbon radicals, and divalent substituted oxyhydrocarbon radicals.

9. The composition of claim 1 wherein said ultraviolet light absorbing component is about 0.05% to about 5% by weight of said composition.

10. A corneal contact lens, an intraocular lens or a corneal intrastromal lens comprising the composition of claim 1, provided said composition is optically clear.

11. A composition curable into a cross-linked polymer composition comprising a cross-linkable siloxane polymer, a cross-linking component capable of reacting with said cross-linkable siloxane polymer, and at least one component capable of reacting with at least one of said cross-linkable siloxane polymer and said cross-linking component in an amount effective to render said cross-linked polymer composition ultraviolet light absorbing, said component having the following structure ##STR11## 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, R² is selected from the group consisting of divalent hydrocarbon radicals, divalent substituted hydrocarbon radicals, oxo, divalent oxyhydrocarbon radicals and divalent substituted oxyhydrocarbon radicals, each R³ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, aryl radicals, substituted aryl radicals and fluoro radical, R is selected from the group consisting of H and CH=CH₂, and c is an integer in the range of 1 to about 20.

12. The composition of claim 11 wherein R² is selected from the group consisting of methylene, substituted methylene, ethylene, substituted ethylene, oxo, divalent oxyhydrocarbon radicals, and divalent substituted oxyhydrocarbon radicals.

13. A compound having the following formula ##STR12## 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, R² is selected from the group consisting of divalent hydrocarbon radicals, divalent substituted hydrocarbon radicals, oxo, divalent oxyhydrocarbon radicals and divalent substituted oxyhydrocarbon radicals, each R³ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, aryl radicals and substituted aryl radicals, R is selected from the group consisting of H and CH=CH₂, and c is an integer in the range of 1 to about 20.

14. The compound of claim 13 wherein each R³ is independently selected from the group consisting of alkyl radicals and aryl radicals.

15. The compound of claim 13 wherein R¹ is selected from alkyl radicals. PG,33

16. The compound of claim 13 which has the following formula ##STR13##

17. The compound of claim 13 wherein each R³ is independently selected from the group consisting of alkyl radicals having 1 to about 4 carbon atoms, substituted alkyl radicals having 1 to about 4 carbon atoms, alkoxy radicals having 1 to about 4 carbon atoms, substituted alkoxy radicals having 1 to about 4 carbon atoms, phenyl radicals and substituted phenyl radicals.

18. The compound of claim 13 wherein each R³ is a methyl radical and c is an integer in the range of 1 to about 4.

19. The compound of claim 13 wherein R² is an alkylene radical.

20. A compound or mixture of compounds selected from the group consisting of2-[3'"'"'-t-butyl-2'"'"'-hydroxy-5'"'"'-(2"(7'"'"'"-vinyl octamethyl tetrasiloxane) ethyl) phenyl]-5-chloro-2H-benzotriazole, 2-[3'"'"'-t-butyl-2'"'"'hydroxy-5'"'"'octamethyl tetrasiloxane) ethyl) phenyl]5-chloro-2H-benzotriazole and mixtures thereof.

21. A compound having the following formula ##STR14## wherein X is selected from the group consisting of H, alkoxy radicals and halogen, R¹ is selected from the group consisting of alkyl radicals, R² is selected from the group consisting of divalent hydrocarbon radicals, divalent substituted hydrocarbon radicals, oxo, divalent oxyhydrocarbon radicals and divalent substituted oxyhydrocarbon radicals, each R³ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, aryl radicals and substituted aryl radicals, R is selected from the group consisting of R³, H and CH=CH₂, and c is an integer in the range of 1 to about 20.

22. A compound having the following formula ##STR15## 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, R² is selected from the group consisting of methylene, substituted emthylene, ethylene, substituted ethylene, oxo, divalent oxyhydrocarbon radicals and divalent substituted oxyhydrocarbon radicals, each R³ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, aryl radicals and substituted aryl radicals, R is selected from the group consisting of R³, H and CH=CH₂, and c is an integer in the range of 1 to about 20.