Hydrophilic Polysiloxane Macromonomer, and Production and Use of the same

• US 20090234089A1
• Filed: 02/06/2009
• Published: 09/17/2009
• Est. Priority Date: 02/08/2008
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: AsahiKasei Aime Co. Ltd. (Asahi Kasei Corporation)
• Inventors: UEYAMA, Hiroyuki, IWATA, Junichi, IKAWA, Seiichiro
• Granted Patent: US 8,129,442 B2
• Time in Patent Office: Days
• US Class Current: 526/279
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/061 Polyesters; Polycarbonates
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 8/42 Introducing metal atoms or metal-containing groups
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Problem to be Solved To provide an ophthalmic lens, which can be more safely worn, that is, to provide a material, which is transparent and has high oxygen permeability and a high hydrophilic property, and to provide a novel monomer to be a raw material thereof.

Solution A hydrophilic polysiloxane macromonomer contains polyoxyethylene as a hydrophilic side chains in a polysiloxane main chain, wherein transparency, oxygen permeability, and hydrophilic properties of the material are controlled by regulating the length of the polysiloxane main chain, the length of the hydrophilic polyoxyethylene side chains, and the number of the side chains.

Claims

1. A hydrophilic polysiloxane macromonomer represented by general formula (1):

2. The hydrophilic polysiloxane macromonomer according to claim 1, wherein a and b, which are presented in the general formula (1), represent 25-200 and 2-20, respectively.

3. The hydrophilic polysiloxane macromonomer according to claim 1, wherein n presented in the general formula (1) represents 5 to 20.

4. The hydrophilic polysiloxane macromonomer according to claim 1, wherein a and b, which are presented in the general formula (1), represent 25-160 and 3-10, respectively, and n represents 5-15.

5. A method of producing the hydrophilic polysiloxane macromonomer according to claim 1, comprising a step of producing a polysiloxane intermediate represented by general formula (2) described below:

6. The method of producing the hydrophilic polysiloxane macromonomer according to claim 5, wherein the step of producing the intermediate represented by general formula (2) is carried out using an acid catalyst.

7. The method of producing the hydrophilic polysiloxane macromonomer according to claim 5, wherein the step of producing the intermediate represented by general formula (2) is carried out by ring-opening polymerization of cyclic dimethylsiloxane, cyclic siloxane having hydrosilane (Si—

H), and siloxane having (meth)acrylic groups at both terminals.

8. The method of producing the hydrophilic polysiloxane macromonomer according to claim 7, wherein the step of producing the intermediate represented by general formula (2) is stopped the reaction by neutralization reaction with a basic aqueous solution.

9. A method of producing the hydrophilic polysiloxane macromonomer according to claim 1, comprising hydrosilylation reaction of the intermediate represented by general formula (2) with polyethylene glycol allyl ether represented by general formula (3):

10. The method of producing the hydrophilic polysiloxane macromonomer according to claim 9, wherein a platinum-containing catalyst is used as the catalyst for the hydrosilylation reaction.

11. The method of producing the hydrophilic polysiloxane macromonomer according to claim 9, further comprising the step of washing the hydrophilic polysiloxane macromonomer with a solvent.

12. A homopolymer of the hydrophilic polysiloxane macromonomer according to claim 1, or a copolymer copolymerized with one or more polymerizable monomers.

13. An ophthalmic lens material comprising at least a polymer according to claim 12.

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

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

16. The hydrophilic polysiloxane macromonomer according to claim 2, wherein n presented in the general formula (1) represents 5 to 20.

17. The hydrophilic polysiloxane macromonomer according to claim 2, wherein a and b, which are presented in the general formula (1), represent 25-160 and 3-10, respectively, and n represents 5-15.

18. The hydrophilic polysiloxane macromonomer according to claim 3, wherein a and b, which are presented in the general formula (1), represent 25-160 and 3-10, respectively, and n represents 5-15.

19. The method of producing the hydrophilic polysiloxane macromonomer according to claim 10, further comprising the step of washing the hydrophilic polysiloxane macromonomer with a solvent.

20. A homopolymer of the hydrophilic polysiloxane macromonomer according to claim 2, or a copolymer copolymerized with one or more polymerizable monomers.