TRANSPARENT GEL AND CONTACT LENSE FROM THE SAME

• US 20090012205A1
• Filed: 01/13/2006
• Published: 01/08/2009
• Est. Priority Date: 01/20/2005
• Status: Active Grant

• Current Assignee: Menicon Company Limited, Mitsubishi Gas Chemical Company Incorporated (Mitsubishi Electric Corporation)
• Original Assignee: Menicon Company Limited, Mitsubishi Gas Chemical Company Incorporated (Mitsubishi Electric Corporation)
• Inventors: Nakada, Kazuhiko, Nakase, Takahito, Yamamoto, Akira, Adachi, Takahiro, Minemura, Masahiko
• Granted Patent: US 8,173,720 B2
• Time in Patent Office: Days
• US Class Current: 523/107
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08G 77/448 containing polycarbonate sequences
• CPC Class Codes: C08L 2201/00 Properties
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• 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 33/24 Homopolymers or copolymers of amides or imides
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 69/00 Compositions of polycarbonates; Compositions of derivatives of polycarbonates
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/10 Block- or graft-copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A transparent gel is disclosed which has an interpenetrating polymer network of a copolymer containing a polysiloxane structure and a polycarbonate structure and a hydrophilic polymer obtained by polymerizing a hydrophilic monomer. The transparent gel is useful as a cultivation substrate, a container for storage and an ophthalmic material, comprising an easily synthesizable and purifiable silicon-containing resin, wherein a gel strength, transparency, oxygen permeability, birefringence and other characteristics are excellent.

Claims

1. A transparent gel comprising a copolymer having a polysiloxane structure and a polycarbonate structure and a hydrophilic polymer obtained by polymerizing a hydrophilic monomer;

the gel having an interpenetrating polymer network of the copolymer and the hydrophilic polymer.

2. The transparent gel of claim 1, wherein the above copolymer having a polysiloxane structure and a polycarbonate structure is derived from a compound shown by the general formula (A) and a compound shown by the general formula (B) and a compound forming a carbonic acid ester.

(wherein R¹ and R² are, respectively and independently, a member selected from the group consisting of a hydrogen atom, an alkyl group of C1-C10, an aryl group of C6-C12, an alkenyl group of C2 to C5, an alkoxy group of C1 to C5 and an aralkyl group of C7-C17, and when those groups have a carbon atom, those group may contain a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5, Y is a group shown by the formula:

(wherein R³ to R⁶ are respectively a member selected from the group consisting of a hydrogen atom, an alkyl group of C1 to C10, an alkenyl group of C2 to C10, an alkoxy group of C1 to C10 and an aryl group of C6 to C12, or both R3 and R4 and both R5 and R6 are respectively combined together to form a carbon ring or a heterocyclic ring, and when those group contain a carbon atom, those group may have a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5, and a is an integer of 0 to

     20), or a formula;

(wherein R⁷ to R¹⁴ are respectively and independently a member selected from the group consisting of a hydrogen atom, an alkyl group of C1 to C5, an aryl group of C6 to C12, an alkenyl group of C2 to C5, an alkoxy group of C1 to C5 and an aralkyl group of C7 to C17, and when those group contain a carbon atom, those group may have a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5. R¹⁵ is an aliphatic group of C1 to C6 or only shows a bond. X is a single polymer or a random copolymer of —

SiO(R¹⁶)(R¹⁷)— and

/or —

SiO(R¹⁸)(R¹⁹)— and

its polymerization degree is 0 to 200, and R¹⁶ to R¹⁹ are respectively and independently a member selected from the group consisting of a hydrogen atom, an alkyl group of C1 to C5, an aryl group of C6 to C12, an alkenyl group of C2 to C5, an alkoxy group of C1 to C5 and an aralkyl group of C7 to C17, and when those group contain a carbon atom, those group may have a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5).

3. The transparent gel of claim 1, wherein the above hydrophilic monomer is a monomer containing a nitrogen atom.

4. The transparent gel of claim 3, wherein the above monomer containing a nitrogen atom is N-vinyl pyrrolidone, N,N-dimethylacrylamide and/or N-methyl-3-methylidene pyrrolidone.

5. The transparent gel of claim 2, wherein the compound shown by the above formula (A) is a member selected from the group consisting of 9,9-bis(4-hydroxyphenyl) fluorene, 9,9-bis(4-hydroxy-3-methylphenyl) fluorene and 9,9-bis(4-hydroxy-2-methylphenyl) fluorene.

6. The transparent gel of claim 2, wherein a ratio of the polysiloxane structure to the polycarbonate structure contained in the above copolymer is 25:

75 to 75;

25 by weight.

7. The transparent gel of claim 1, wherein a ratio of the above copolymer to the above hydrophilic monomer is 5:

95 to 40;

60 by weight.

12. A contact lens comprising the transparent gel of claim 1.

13. The transparent gel of claim 1, wherein a ratio of the polysiloxane structure to the polycarbonate structure combined in the above copolymer is 25:

75 to 75;

25 by weight.

16. The contact lens of claim 12, wherein the copolymer has a polysilixane structure and a polycarbonate structure is derived from a compound shown by the general formula (A) and a compound shown by the general formula (B) and a compound forming a carbonic acid ester.

(wherein R¹ and R² are, respectively and independently, a member selected from the group consisting of a hydrogen atom, an alkyl group of C1-C10, an aryl group of C6-C12, an alkenyl group of C2 to C5, an alkoxy group of C1 to C5 and an aralkyl group of C7-C17, and when those groups have a carbon atom, those group may contain a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5, Y is a group shown by the formula:

(wherein R³ to R⁶ are respectively a member selected from the group consisting of a hydrogen atom, an alkyl group of C1 to C10, an alkenyl group of C2 to C10, an alkoxy group of C1 to C10 and an aryl group of C6 to C12, or both R³ and R⁴ and both R⁵ and R⁶ are respectively combined together to form a carbon ring or a heterocyclic ring, and when those group contain a carbon atom, those group may have a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5, and a is an integer of 0 to

     20), or a formula;

(wherein R⁷ to R¹⁴ are respectively and independently a member selected from the group consisting of a hydrogen atom, an alkyl group of C1 to C5, an aryl group of C6 to C12, an alkenyl group of C2 to C5, an alkoxy group of C1 to C5 and an aralkyl group of C7 to C17, and when those group contain a carbon atom, those group may have a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5. R¹⁵ is an aliphatic group of C1 to C6 or only shows a bond. X is a single polymer or a random copolymer of —

SiO(R¹⁶)(R¹⁷)— and

/or —

SiO(R¹⁸)(R¹⁹)— and

its polymerization degree is 0 to 200, and R¹⁶ to R¹⁹ are respectively and independently a member selected from the group consisting of a hydrogen atom, an alkyl group of C1 to C5, an aryl group of C6 to C12, an alkenyl group of C2 to C5, an alkoxy group of C1 to C5 and an aralkyl group of C7 to C17, and when those group contain a carbon atom, those group may have a substituent selected from the group consisting of an alkyl group of C1 to C5, an alkenyl group of C2 to C5 and an alkoxy group of C1 to C5).

17. The contact lens of claim 16, wherein the compound shown by the above formula (A) is a member selected from the group consisting of 9,9-bis(4-hydroxyphenyl) fluorene, 9,9-bis(4-hydroxy-3-methylphenyl) fluorene and 9,9-bis(4-hydroxy-2-methylphenyl) fluorene.

18. The contact lens of claim 16, wherein a ratio of the polysiloxane structure to the polycarbonate structure contained in the above copolymer is 25:

75 to 75;

25 by weight.

19. The contact lens of claim 12, wherein the above hydrophilic monomer is a monomer containing a nitrogen atom.

20. The contact lens of claim 19, wherein the above monomer containing a nitrogen atom is N-vinyl pyrrolidone, N,N-dimethylacrylamide and/or N-methyl-3-methylidene pyrrolidone.

21. The contact lens of claim 12, wherein a ratio of the polysiloxane structure to the polycarbonate structure contained in the above copolymer is 25:

75 to 75;

25 by weight.

8. A method for producing a transparent gel comprising a process of polymerization after dissolving a copolymer containing a polysiloxane structure and a polycarbonate structure in a hydrophilic monomer solution.

9. The method for producing a transparent gel of claim 8, wherein a process of adding a cross linking agent is included upon dissolving the copolymer in the hydrophilic monomer solution.

10. The method for producing a transparent gel of claim 9, wherein the above cross linking agent is allyl methacrylate or diethyleneglycol diallyl ether.

11. The method for producing a transparent gel of claim 10, wherein the polymerization is conducted in a mold.

14. The method for producing a transparent gel of claim 9, wherein the polymerization is conducted in a mold.

15. The method for producing a transparent gel of claim 8, wherein the polymerization is conducted in a mold.