Silicone monomer

• US 8,580,904 B2
• Filed: 03/05/2010
• Issued: 11/12/2013
• Est. Priority Date: 03/09/2009
• Status: Active Grant

• Current Assignee: NOF Corporation
• Original Assignee: NOF Corporation
• Inventors: Matsuoka, Yosuke, Yoshioka, Nobuyuki, Sorimachi, Mao, Sakamoto, Nobuyuki
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Miller, David L
• Application Number:
  US13/255,480
• Publication Number:
  US 20110319583A1
• Time in Patent Office: 1,348 Days
• Field of Search: 526/279, 526/264
• US Class Current: 526/279
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• 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: C08F 130/08 containing silicon
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

The invention provides a silicone monomer which is suitable for the manufacture of ophthalmic devices, such as contact lenses, intraocular lenses, and keratoprosthesis, a monomer composition containing the monomer, and a polymer which fulfills both surface hydrophilicity and oxygen permeability at the same time. The silicone monomer of the present invention is represented by the formula (1a) or (1b):

(X: a monovalent C2 to C6 organic group having one or more —OH and optionally one O or N in its main chain; Z¹ to Z⁹: a C1 to C4 alkyl group; n: 1 to 3; a and b: 0 or 1).

Claims

1. A silicone monomer represented by the formula (1a) or (1b):

2. The silicone monomer of claim 1, wherein X is selected from the groups represented by formulae (2a) to (2f):

3. A monomer composition comprising:

at least one silicone monomer according to claim 1, and

a hydrophilic monomer selected from the group consisting of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, N,N-dimethylacrylamide, 2-(methacryloyloxyethyl)-2-(trimethylammonioethyl) phosphate, and mixtures thereof,

wherein the content of said silicone monomer is 20 to 60 mass % of a total amount of said composition.

4. A polymer obtained by polymerization of a monomer composition according to claim 3.

5. A monomer composition comprising:

at least one silicone monomer according to claim 2, and

a hydrophilic monomer selected from the group consisting of 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, N,N-dimethylacrylamide, 2-(methacryloyloxyethyl)-2-(trimethylammonioethyl) phosphate, and mixtures thereof,

wherein the content of said silicone monomer is 20 to 60 mass % of a total amount of said composition.

6. A polymer obtained by polymerization of a monomer composition according to claim 5.