ACRYLOYL MATERIALS FOR MOLDED PLASTICS

• US 20080004383A1
• Filed: 12/12/2006
• Published: 01/03/2008
• Est. Priority Date: 06/30/2006
• 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: Koyama, Hiroya, Kohara, Takehiro, Umeda, Satoshi, Nakamura, Masataka, Yokota, Mitsuru, Kamasaka, Kimihiro, Kiguchi, Shinya
• Granted Patent: US 8,569,538 B2
• Time in Patent Office: Days
• US Class Current: 524/284
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08K 5/10 Esters; Ether-esters
• CPC Class Codes: C08K 5/5425 containing at least one C=C bond
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

In one aspect, the invention relates to methods of synthesizing acryloyl compounds, comprising the step of hydrosilylating a compound having the structure:

with a compound having the structure A-H, wherein A comprises a siloxanyl group, to yield a compound having the structure:

Compounds and compositions produced thereby can effectively attain a satisfactory balance between high oxygen permeability and hydrophilicity while achieving an acceptably low concentration of undesirable impurities. 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. An acryloyl compound comprising a structure:

2. The compound of claim 1, wherein R¹ is hydrogen or methyl.

3. The compound of claim 1, wherein X is a hydrolysable alkyl group selected from a residue of dihydropyran, a residue of alkyl halide, a residue of tosyloxyalkane, a residue of diazoalkane, a residue of dialkyl sulfate, a residue of an acid anhydride, a residue of an acid halide, a residue of a halogenated silane, and a residue of a silazane.

4. A composition comprising the compound of claim 1 or a hydrolysis product thereof or a polymer comprising residues of the compound of claim 1 or a hydrolysis product thereof.

5. The composition of claim 4, wherein the polymer is a copolymer comprising residues of 2-hydroxyethyl methacrylate.

6. The composition of claim 4, wherein an epoxide moiety or a diol moiety is present in a concentration of less than about 100 ppm.

7. A molded article, ophthalmic lens, or contact lens comprising the composition of claim 4.

8. A method of synthesizing an acryloyl compound, comprising the step of hydrosilylating a first compound having the structure:

9. The method of claim 8, wherein R¹ is hydrogen or methyl.

10. The method of claim 8, wherein X is a hydrolysable alkyl group selected from a residue of dihydropyran, a residue of alkyl halide, a residue of tosyloxyalkane, a residue of diazoalkane, a residue of dialkyl sulfate, a residue of an acid anhydride, a residue of an acid halide, a residue of a halogenated silane, and a residue of a silazane.

11. The method of claim 8, wherein the siloxanyl group comprises a structure:

12. The method of claim 8, wherein X is a hydrolysable group, further comprising the step of hydrolyzing or solvolyzing the third compound to yield a fourth compound having the structure:

13. The method of claim 8, further comprising the step of providing the first compound by treating allyl glycidyl ether with an alkylacrylic acid to yield a starting compound having the structure:

14. The product of the method of claim 8.

15. A method for producing a siloxanyl monomer comprising a structure:

16. The method of claim 15, further comprising the sequential steps of:

a) mixing the reaction mixture with a hydrocarbon solvent and a hydrophilic solvent;

b) allowing the mixture to form two layers; and

c) separating the two layers,

thereby removing the unsaturated compound from the reaction mixture.

17. The method of claim 15, wherein the unsaturated compound is removed from the reaction mixture by thin film distillation.

18. The method of claim 15, wherein the unsaturated compound has a structure:

19. The method of claim 15, wherein the siloxanyl compound has a structure:

20. The product of the method of claim 15.