Method for manufacturing hydrophilic silicone macromer

• US 9,133,221 B2
• Filed: 08/26/2014
• Issued: 09/15/2015
• Est. Priority Date: 12/29/2011
• Status: Active Grant

• Current Assignee: Pegavision Corporation
• Original Assignee: Pegavision Corporation
• Inventors: Ting, Wei-Jia, Li, Heng-Yi, Lai, Yu-Chin, Chang, Han-Yi
• Primary Examiner(s): Jackson, Shawquia
• Application Number:
  US14/469,386
• Publication Number:
  US 20140364624A1
• Time in Patent Office: 385 Days
• Field of Search: 556/450
• US Class Current: 1/1
• CPC Class Codes: C07F 7/10 containing nitrogen having a Si-N linkage
• CPC Class Codes: C07F 9/062 Organo-phosphoranes without P-C bonds
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A method for manufacturing a hydrophilic silicone macromer is provided. A hydrosilylation between a Si—H bond of a polysiloxane and a C═C bond of a hydrophilic mononmer is performed by using a rhodium-containing catalyst to form the polysiloxane having a hydrophilic side chain having an amide group or a phosphoryl choline group. After performing an end-capping reaction, the hydrophilic silicone macromer is formed.

Claims

1. A method for manufacturing a hydrophilic silicone macromer, comprising the steps of:

performing a ring-opening insertion, wherein a cyclic siloxane and a cyclic hydrogen siloxane are subject to a ring-opening reaction, and then are inserted into an asymmetrically end-capped polydialkylsiloxane having a terminal reactive hydrogen to form an asymmetrically end-capped polysiloxane having a silicon-hydrogen (Si-H) bond, in which the terminal reactive hydrogen is derived from a hydroxyl group or an amino group;

performing a hydrosilylation between the Si-H bond of the asymmetrically end-capped polysiloxane and a C═

C bond of a hydrophilic monomer by using a rhodium-containing catalyst to form an asymmetrically end-capped polysiloxane intermediate having a hydrophilic side chain, wherein the hydrophilic monomer has an amide group or a phosphoryl choline group; and

performing an end-capping reaction between the terminal reactive hydrogen of the asymmetrically end-capped polysiloxane intermediate and an electrophilic group of an ethylenically unsaturated compound to form the hydrophilic silicone macromer having only one ethylenically unsaturated group.

2. The method of claim 1, wherein the step of performing the hydrosilylation is in an environment of 40 to 150°

C.

3. The method of claim 1, wherein the hydrophilic monomer having the amide group selected from the group comprising N-vinylpyrrolidone, N-allylpyrrolidone, N-vinyl-N-methylacetamide and a combination thereof.

4. The method of claim 1, wherein the hydrophilic monomer having a phosphoryl choline group is 2-methacryloyloxyethyl phosphorylcholine.

5. The method of claim 1, wherein the rhodium-containing catalyst is tris(dibutylsul fide)rhodium trichloride.

6. The method of claim 1, wherein the hydrophilic silicone macromer has a molecular weight in a range of about 500 to about 6,000.

7. The method of claim 1, wherein the weight ratio of the hydrophilic monomer used for the hydrosilylation and the hydrophilic silicone macromer to be manufactured is in a range of about 5:

100 to about 90;

100.

8. The method of claim 1, wherein the cyclic siloxane is 1,1,3,3,5,5,7,7-octamethylcyclotetrasiloxane, and the cyclic hydrogen siloxane is 1,3,5,7-tetramethyltetrasiloxane.

9. The method of claim 1, wherein the ethylenically unsaturated compound is selected from the group comprising isocyanatoethyl methacrylate, methacryloyl chloride, methacrylic anhydride and a combination thereof.