Acryloyl materials for molded plastics

• US 8,569,538 B2
• Filed: 12/12/2006
• Issued: 10/29/2013
• 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: Nakamura, Masataka, Yokota, Mitsuru, Kohara, Takehiro, Kamasaka, Kimihiro, Koyama, Hiroya, Kiguchi, Shinya, Umeda, Satoshi
• Primary Examiner(s): Richter, Johann R
• Assistant Examiner(s): Sawyer, Jennifer C
• Application Number:
  US11/609,724
• Publication Number:
  US 20080004383A1
• Time in Patent Office: 2,513 Days
• Field of Search: None
• US Class Current: 560/129
• 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. A method for producing a siloxanyl monomer composition, the composition comprising monomers having the structures:

2. The method of claim 1, wherein the molar ratio of the unsaturated compounds to the siloxanyl compound is from about 2.5:

1 to about 3;

1 during the reacting step.

3. The method of claim 2, further comprising the sequential steps of:

a) mixing the reaction mixture with a hydrocarbon solvent and water and/or a C₁-C₅ alcohol;

b) allowing the mixture to form two layers; and

c) separating the two layers,

thereby removing the unsaturated compounds from the reaction mixture.

4. The method of claim 2, wherein the unsaturated compounds are removed from the reaction mixture by thin film distillation.

5. The method of claim 2, wherein the unsaturated compounds have the structures:

6. The method of claim 2, wherein the siloxanyl compound has a structure: