Soluble silicone prepolymers

• US 8,399,539 B2
• Filed: 11/19/2011
• Issued: 03/19/2013
• Est. Priority Date: 06/29/2007
• 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: Fujisawa, Kazuhiko, Yokota, Mitsuru, Nakamura, Masataka
• Primary Examiner(s): Loewe, Robert S
• Application Number:
  US13/300,576
• Publication Number:
  US 20120065348A1
• Time in Patent Office: 486 Days
• Field of Search: 526/279
• US Class Current: 523/107
• 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 220/26 Esters containing oxygen in addition to the carboxy oxygen
• CPC Class Codes: C08F 220/387 and containing nitrogen and oxygen
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

In one aspect, the invention relates to silicon-based prepolymers. The disclosed prepolymers exhibit satisfactory solubility in aqueous solutions or hydrophilic solutions and can overcome undesirable shrinkage, expansion, and related problems possessed by conventional silicone monomers and related conventional polymerization techniques by producing hydrogels from a crosslinkable prepolymer. Also disclosed are polymers and molded articles produced from the disclosed prepolymers, which attain a satisfactory oxygen permeability. Also disclosed are methods for producing the disclosed prepolymers. 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 silicone prepolymer comprising:

at least one silicone-containing residue having a structure represented by the formula;

2. The prepolymer of claim 1, further comprising at least one at least one hydrophilic residue having a structure represented by the formula:

3. The prepolymer of claim 2, wherein the hydrophilic residue comprises one or more residues of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, N-vinylpyrrolidone, N-vinylformamide, N-vinylacetamide, (meth)acrylic acid, N-vinyl-2-piperidone, N-vinyl-2-caprolactam, N-vinyl-3-methyl-2-caprolactam, N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-4-methyl-2-caprolactam, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, or N-vinylimidazole.

4. The prepolymer of claim 1, wherein the polymerizable residue is obtained by reacting a unit having a structure represented by the formula:

5. The prepolymer of claim 4, wherein Z comprises one or more of:

6. The prepolymer of claim 4, wherein the compound having at least one

polymerizable group is 2-isocyanatoethyl(meth)acrylate, (meth)acryloyl isocyanate,

7. The prepolymer of claim 1, wherein at least one polymerizable moiety has a structure represented by the formula:

8. The prepolymer of claim 1, wherein the prepolymer has a silicon content of from about 13% to about 20% by weight.

9. The prepolymer of claim 1, wherein the content of the polymerizable unit is from about 0.1 to about 15 mol%, based on the prepolymer.

10. The prepolymer of claim 1, wherein the prepolymer has a solubility of not less than about 50% by weight, based on solid content of the prepolymer, in a water-soluble solvent.

11. The prepolymer of claim 10, wherein the prepolymer has a solubility of not less than about 50% by weight, based on solid content of the prepolymer, in a water-soluble solvent comprising from about 1% to about 10% by weight of polyvinylpyrrolidone.

12. The prepolymer of claim 10, wherein the water-soluble solvent comprises one or more of ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, or ethylene glycol-propylene glycol copolymer or a mixture thereof.

13. A polymer obtained by polymerizing the prepolymer of claim 1.

14. An ophthalmic lens comprising the polymer according to claim 13.

15. A contact lens comprising the polymer according to claim 13.