Ultraviolet light absorbing compounds, silicone compositions and methods for making same

• US 5,466,768 A
• Filed: 05/06/1994
• Issued: 11/14/1995
• Est. Priority Date: 04/25/1991
• Status: Expired due to Term

• Current Assignee: Abbott Medical Optics Incorporated (Johnson & Johnson)
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: Yang, Shih-Liang S.
• Primary Examiner(s): Lesmes, George F.
• Assistant Examiner(s): PEZZUTO, HELEN LEE
• Application Number:
  US08/239,175
• Time in Patent Office: 557 Days
• Field of Search: 528/27, 528/15, 525/479
• US Class Current: 528/15
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• 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: C07F 7/21 Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
• 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 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/16 to hydroxyl groups
• 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 77/26 nitrogen-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 is disclosed which comprises silicone base polymer and ultraviolet light absorbing component present as, or derived from, one or more silicon-containing ultraviolet light absorbing benzotriazole derivatives. Also disclosed are methods for producing such silicone compositions and derivatives. Such silicone compositions, which are preferably optically clear, are useful as lens materials.

Claims

1. A compound having one of the following formulas ##STR24## and mixtures thereof, wherein B is ##STR25## each x is independently selected from the group consisting of H, monovalent hydrocarbon radicals, monovalent substituted hydrocarbon radicals, hydroxyl radicals, amino radicals, carboxyl radicals, alkoxy radicals, substituted alkoxy radicals, and halogen radicals;

each R¹ is independently selected from the group consisting of H, alkyl radicals, alkoxy radical, hydroxyl radicals, amino radicals and carboxyl 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, H, alkenyl radicals, substituted alkenyl radicals, R² -B, aryl radicals, substituted aryl radicals and fluoro radical;

R is selected from the group consisting of H, alkenyl radicals and substituted alkenyl radicals, alkenoxy radicals, substituted alkenoxy radicals, acryloxy alkyl radicals and substituted acryloxy alkyl radicals;

each R⁴ is independently selected from the group consisting of R and R³, provided that at least one of the R⁴ s is R;

c is an integer in the range of 1 to about 10,000; and

d is an integer in the range of 0 to about 100.

2. The compound of claim 1 wherein each R³ is independently selected from the group consisting of alkyl radicals and aryl radicals, and said alkenyl radicals and substituted alkenyl radicals which contain a terminal carbon-carbon double bond have 2 to about 6 carbon atoms.

3. The compound of claim 1 selected from the group consisting of compounds having the structure (1) and the mixtures thereof, and R² is bonded to the ortho position or to the para position relative to the phenolic hydroxyl group of B.

4. The compound of claim 3 wherein R² is bonded to the ortho position relative to the phenolic hydroxyl group of B.

5. The compound of claim 4 wherein all of the R¹ s are H.

6. The compound of claim 1 wherein no more than one of the Xs is other than H, no more than one of the R¹ s is other than H, 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 compound of claim 1 wherein each R³ is a methyl radical and c is an integer in the range of 1 to about 4 and d is an integer in the range of 0 to about 3.

8. The compound of claim 1 wherein R² is an alkylene radical.

9. A compound having the formula ##STR26## wherein B is ##STR27## each x is independently selected from the group consisting of H, monovalent hydrocarbon radicals, monovalent substituted hydrocarbon radicals, hydroxyl radicals, amino radicals, carboxyl radicals, alkoxy radicals, substituted alkoxy radicals, and halogen radicals;

each R¹ is independently selected from the group consisting of H, alkyl radicals, alkoxy radical, hydroxyl radicals, amino radicals and carboxyl 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 R⁴ is independently selected from the group consisting of alkyl radicals, substituted alkyl radicals, alkoxy radicals, substituted alkoxy radicals, H, alkenyl radicals, substituted alkenyl radicals, R² -B, aryl radicals, substituted aryl radicals, fluoro radical, alkenoxy radicals, substituted alkenoxy radicals, acryloxy alkyl -radicals and substituted acryloxy alkyl radicals, provided that at least one of the R⁴ s is selected from the group consisting of H, alkenyl radicals, substituted alkenyl radicals, alkenoxy radicals, substituted alkenoxy radicals, acryloxy alkyl radicals and substituted acryloxy alkyl radicals; and

d is an integer in the range of 0 to about 100.

10. The compound of claim 9 wherein said alkenyl radicals and substituted alkenyl radicals which contain a terminal carbon-carbon double bond have 2 to about 6 carbon atoms.

11. The compound of claim 9 wherein no more than one of the Xs is other than H, and no more than one of the R¹ s is other than H.

12. The compound of claim 9 wherein d is an integer in the range of 0 to about 3.

13. The compound of claim 9 wherein R² is an alkylene radical.

14. A method for producing an ultraviolet light absorbing compound comprising:

contacting a functional benzotriazole derivative with a siloxane component having at least two functional hydride groups at conditions effective to chemically react the functional group of the benzotriazole derivative with one of the hydride groups of the siloxane component, thereby forming a hydride functional benzotriazole derivative.

15. The method of claim 14 which further comprises contacting said hydride functional benzotriazole derivative with a functional component selected from the group consisting of compounds containing a plurality of carbon-carbon multiple bonds, compounds containing a carbon-carbon triple bond, compounds with both a hydroxyl group and a carbon-carbon multiple bond, compounds with an acryloxy alkyl group and a carbon-carbon multiple bond and mixtures thereof at conditions effective to chemically react the hydride group of said hydride functional benzotriazole derivative with a functional group present in said functional component, thereby forming an unsaturation functional benzotriazole derivative.

16. The method of claim 14 wherein said contacting occurs in the presence of a platinum group metal-containing catalyst in an amount effective to promote said chemical reaction.

17. The method of claim 15 wherein each of said contactings occurs in the presence of an effective amount of platinum group metal-containing catalyst.