METHODS FOR PURIFYING SILOXANYL MONOMERS

• US 20080119627A1
• Filed: 03/02/2007
• Published: 05/22/2008
• Est. Priority Date: 11/22/2006
• Status: Abandoned Application

• 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: Koyama, Hiroya, Kiguchi, Shinya, Nakamura, Masataka, Kohara, Takehiro
• Application Number:
  US11/681,406
• Publication Number:
  US 20080119627A1
• Time in Patent Office: Days
• US Class Current: 528/31
• CPC Class Codes: C07F 7/20 Purification, separation

Abstract

Disclosed are reduced pressure distillation methods for purifying siloxanyl monomers in the presence of at least one polymerization inhibitor. In further aspects, the polymerization inhibitor can be an alkylhydroquinone or a hydroxynaphthalene. Also disclosed are compounds purified by the disclosed methods and polymers produced therefrom. 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 method for purifying a siloxanyl monomer, the method comprising the step of reduced pressure distillation of the siloxanyl monomer in the presence of at least one polymerization inhibitor comprising an alkylhydroquinone or a hydroxynaphthalene.

2. The method of claim 1, further comprising the step of collecting the distilled siloxanyl monomer.

3. The method of claim 1, wherein the at least one polymerization inhibitor comprises a hydroxynaphthalene.

4. The method of claim 3, wherein the hydroxynaphthalene is an alkoxy naphthol, a dihydroxynaphthol, or a dialkoxynaphthol.

5. The method of claim 3, wherein the hydroxynaphthalene is 4-methoxy-1-naphthol.

6. The method of claim 1, wherein the at least one polymerization inhibitor comprises an alkylhydroquinone comprising at least one alkyl group.

7. The method of claim 6, wherein the alkyl group comprises a substituted or unsubstituted C₁ to C₁₂ alkyl group.

8. The method of claim 6, wherein the alkyl group is a tertiary alkyl group.

9. The method of claim 6, wherein the alkylhydroquinone is 2-t-butylhydroquinone or 2,6-di-t-butylhydroquinone.

10. The method of claim 1, wherein the siloxanyl monomer comprises at least one polymerizable carbon-carbon unsaturated bond in an alkylacryloyl moiety.

11. The method of claim 1, wherein the siloxanyl monomer is represented by the following Formula (A1-1) or (A1-2):

12. The method of claim 11, wherein A is a group represented by the following Formula (B1):

13. The method of claim 11, wherein A is a group represented by the following Formula (B2):

14. The method of claim 1, wherein the distillation is thin film distillation.

15. The method of claim 1, wherein the distillation is carried out at a temperature of at least 110°

C.

16. The method of claim 1, further comprising the step of removing at least a portion of the at least one polymerization inhibitor.

17. The method of claim 16, wherein the step of removing at least a portion of the at least one polymerization inhibitor is performed by washing of the reaction mixture with an alkaline aqueous solution and treatment with active carbon.

18. A compound purified by the method of claim 1.

19. A polymer comprising at least one residue of a compound of claim 18.

20. A molded article, ophthalmic lens, or contact lens comprising the polymer of claim 19.