HYDROLYSIS-RESISTANT SILICONE COMPOUNDS

• US 20080081894A1
• Filed: 11/20/2006
• Published: 04/03/2008
• Est. Priority Date: 09/29/2006
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson), Toray Industries Incorporated
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson), Toray Industries Incorporated
• Inventors: Nakamura, Masataka, Yokota, Mitsuru, Fujisawa, Kazuhiko, Vanderlaan, Douglas G.
• Granted Patent: US 7,838,698 B2
• Time in Patent Office: Days
• US Class Current: 528/33
• 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 7/0872 Preparation and treatment thereof
• CPC Class Codes: C07F 7/0876 Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si 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 30/08 containing silicon
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

In one aspect, the invention relates to hydrolysis-resistant silicone compounds. In particular, disclosed are sterically hindered hydrolysis-resistant silicone compounds and improved purity hydrolysis-resistant silicone compounds. Also disclosed are processes for making hydrolysis-resistant silicone compounds; the products of the disclosed processes; compositions and polymers comprising the disclosed compounds and products of the disclosed processes; and ophthalmic lenses, for example contact lenses, intraocular lenses, artificial cornea, and spectacle lenses, comprising the disclosed compositions, disclosed polymers, disclosed compounds, and products of the disclosed processes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims

1. A compound having the structure:

2. The compound of claim 1, wherein M is a group comprising an acryloyl group or a methacryloyl group.

3. The compound of claim 1, wherein L has the structure:

4. The compound of claim 1, wherein n is 0, and wherein all of a, b, and c are 1.

5. The compound of claim 1, wherein a is 0;

wherein b and c are 1; and

wherein Z⁹ comprises a methyl group, an ethyl group, a propyl group, a butyl group, or a phenyl group.

6. The compound of claim 3, wherein k is 0, and wherein m is from 1 to 3.

7. The compound of claim 1, wherein two of Z³, Z⁴, and Z⁹ are methyl, and one of Z³, Z⁴, and Z⁹ is ethyl, propyl, or butyl;

wherein two of Z⁵, Z⁶, and Z¹⁰ are methyl, and one of Z⁵, Z⁶, and Z¹⁰ is ethyl, propyl, or butyl; and

two of Z⁷, Z⁸, and Z¹¹ are methyl, and one of Z⁵, Z⁶, and Z¹⁰ is ethyl, propyl, or butyl.

8. The compound of claim 7, wherein Z³, Z⁴, Z⁵, Z⁶, Z⁷, and Z⁸ are methyl, and wherein and Z⁹, Z¹⁰, and Z¹¹ are independently ethyl, propyl, or butyl.

10. A polymer comprising at least one residue of a compound of claim 1.

11. The polymer of claim 10, wherein at least 25% of the polymer comprises residues of a compound of claim 1.

12. An ophthalmic lens comprising the polymer of claim 10.

13. A contact lens comprising the polymer of claim 10.

9. A compound having the structure:

14. A process for making a hydrolysis-resistant silicone compound having a sterically hindered terminal silicon group, the process comprising the step of reacting an alkoxysilyl compound having the structure:

15. The process of claim 14, wherein L has the structure:

16. The process of claim 14, wherein Q¹, Q², and Q³ independently represent alkyl.

17. The process of claim 14, wherein the alkoxysilyl compound has the structure:

18. The process of claim 14, wherein the silyl halide compound has the structure:

19. The process of claim 14, wherein the hydrolysis-resistant silicone compound has the structure:

20. The product of the process of claim 14.

21. A compound having the structure:

22. A polymer comprising at least one residue of a compound of claim 21.

23. A process for making a cyclic siloxane monomer comprising the step of reacting a dihalosilyl compound having the structure:

24. The product of the process of claim 23.

25. A process for making a cyclic siloxane monomer comprising the step of hydrosilylating a unsaturated compound having the structure:

26. The product of the process of claim 25.