Tri-functional UV-absorbing compounds and use thereof

• US 8,324,256 B2
• Filed: 12/17/2009
• Issued: 12/04/2012
• Est. Priority Date: 12/30/2008
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Domschke, Angelika Maria, Winterton, Lynn Cook, Holland, Troy Vernon, Turek, Richard Charles
• Primary Examiner(s): JARRELL, NOBLE E
• Application Number:
  US12/640,019
• Publication Number:
  US 20100168359A1
• Time in Patent Office: 1,083 Days
• Field of Search: None
• US Class Current: 514/359
• CPC Class Codes: C07D 249/20 with aryl radicals directly attached in position 2
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Described herein are tri-functional compounds useful in the production of ophthalmic lenses. The compounds are composed of UV absorber having a polymerization initiator directly or indirectly bonded to the ultraviolet absorber, and an olefinic group directly or indirectly bonded to the ultraviolet absorber. Also described herein are polymers and ophthalmic lenses produced from the tri-functional compounds described herein.

Claims

1. A compound of formula I

Y-L²-Z-L¹-X 

 

I

wherein

Z is the ultraviolet absorber and is a divalent radical of formula (1a) or (1c)

2. The compound of claim 1, wherein the polymerization initiator comprises a phosphine oxide, a peroxide group, or an azide group.

3. The compound of claim 1, wherein the polymerization initiator comprises a monovalent radical of formula IIa, IIb or XI

4. The compound of claim 1, wherein the polymerization initiator comprises a monovalent radical of formula III or Iva or b

5. The compound of claim 1, wherein the polymerization initiator comprises a monovalent radical of formula XII

6. The compound of claim 3, wherein L¹ and L² independent of each other are a covalent bond or a linker of a silicon group, a carbonyl group, a dicarbonyl group, an alkylene group, an alkylene oxide group, an alkylene amine group, or any combination thereof.

7. The compound of claim 3, wherein L¹ and L² independent of each other are a covalent bond or a divalent radical of

—

X₁-E₁-X_b-E₂-X_c—

in which;

X_a is a covalent bond, carbonyl

8. The compound of claim 7, wherein the compound is defined by the formula V

9. The compound of claim 8, wherein X is a monovalent radical of the formula VI

10. The compound of claim 7, wherein the compound has the formula VII

11. The compound of claim 10, wherein L¹ is a divalent radical of the formula

12. An ophthalmic lens comprising a polymer which is the copolymerization product of a polymerizable composition including one or more vinylic monomers and/or macromers and at least one compound of formula I

Y-L²-Z-L¹-X 

 

I

wherein

Z is a divalent radical of formula (1a) or (1c)

13. The ophthalmic lens of claim 12, wherein the polymerization initiator moiety comprises a monovalent radical of formula IIa, IIb or XI

14. The ophthalmic lens of claim 13, wherein L¹ and L² independent of each other are a covalent bond or a divalent radical of

—

X_a-E₁-X_b-E₂-X_e—

in which;

X_a is a covalent bond, carbonyl

15. A method for making UV-absorbing ophthalmic lenses, comprising the steps of:

a. introducing into a mold a lens-forming material, wherein the lens-forming material comprises one or more vinylic monomers and/or macromers and at least one compound of formula I

Y-L²-Z-L¹-X 

 

I

wherein

Z is a divalent radical of formula (1a) or (1c)

16. The method of claim 15, wherein the polymerization initiator moiety comprises a monovalent radical of formula IIa, IIb or XI