Contact lens material

• US 20030109637A1
• Filed: 11/12/2002
• Published: 06/12/2003
• Est. Priority Date: 07/27/1999
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Martin, Arthur W., Kunzler, Jay F.
• Granted Patent: US 6,762,264 B2
• Time in Patent Office: Days
• US Class Current: 525/100
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 77/06 Preparatory processes C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A method for reducing the modulus of polymer silicone hydrogel compositions by employing monomeric polysiloxanes endcapped with trimethylsilyl to reduce the crosslinking density of the hydrogel. The synthesis consists of a single vessel acid catalyzed ring opening polymerization and may be employed to produce copolymers useful as hydrogel contact lens materials.

Claims

1. In a hydrogel formed from the polymerization product of a monomer mixture comprising silicone prepolymers having the generic formula:

2. The method of claim 1, wherein crosslinking density of said hydrogel decreases as the amount of said T₂ increases.

3. The method of claim 1, wherein dimethacrylate disiloxane (M₂) is represented-by the formula:

4. The method of claim 1, wherein m+n+p of said polysiloxane prepolymer is within a range of about 25 to 50.

5. The method of claim 4, wherein m+n+p of said polysiloxane prepolymer is about 25.

6. The method of claim 1, wherein said polysiloxane prepolymer is endcapped with 1 to 70 mole % trimethylsilyl.

7. The method of claim 6, wherein said prepolymer is endcapped within the range of 25 to 50 mole % trimethylsilyl.

8. The method of claim 7, wherein said prepolymer is endcapped within the range of 40 to 50 mole % trimethylsilyl.

9. The method of claim 1, wherein m+n+p of said polysiloxane prepolymer is about 25 and endcapped with about 50 mole % trimethylsilyl.

10. The method of claim 1, wherein D is octamethylcyclotetrasiloxane.

11. The method of claim 1, wherein D is 1,1,3,3-tetramethyl-1,3-disila-2-oxacyclopentane.

12. The method of claim 1, wherein D is hexamethylcyclotrisiloxane.

13. The method of claim 1, wherein said catalyst is trifluoromethane sulfonic acid.

14. The method of claim 1, wherein T₂ is hexamethyl disiloxane.

15. The method of claim 1, wherein said monomer mixture further comprises a hydrophilic monomer.

16. The method of claim 15, wherein said hydrophilic monomer is an acrylic-containing monomer.

17. The method of claim 16, wherein said hydrophilic monomer is N,N-dimethyl acrylamide.

18. The method of claim 15, wherein said hydrophilic monomer is a vinyl-containing monomer.

19. The method of claim 18, wherein said hydrophilic monomer is N-vinyl pyrrolidone.

20. The method of claim 15, still further comprising a monofunctional, ethylenically unsaturated silicone-containing monomer.

21. The method of claim 20, wherein said monofunctional, ethylenically unsaturated silicone-containing monomer is represented by the formula:

22. The method of claim 1, wherein said monomer mixture further comprises a UV initiator.

23. The method of claim 22, wherein said UV initiator is Darocur 1173.

24. The method of claim 1, wherein said monomer mixture further comprises a diluent.

25. The method of claim 24, wherein said diluent is hexanol.

26. A silicone-containing, hydrogel formed from the polymerization product of a monomer mixture comprising:

(a) polysiloxane prepolymers represented by the formula;

 

wherein;

A is an acitvated unsaturated radical;

A′

is either an activated unsaturated radical or an alkyl group;

R₁-R₁₀ are independently an alkyl, fluoroalkyl, alcohol, ether, or fluoroether group having 1-10 carbons, or an aromatic group having 6-18 carbons;

m, n, and p are independently 0 to 200, m+n+p being from about 23 to 200;

a is 1 to 10; and

b is 0 to 10

 

wherein the silicone prepolymer is prepared by the reaction of dimethacrylate disiloxane (M₂) and cyclic siloxane (D) in the presence of a catalyst, the improvement comprising adding at least one disiloxane (T₂) having the formula;

 

wherein R₁₁-R₁₆ are independently an alkyl group having 1-5 carbons, to the reaction mixture used to form the silicone prepolymer;

(b) a hydrophilic monomer; and

(c) a monofunctional, ethylenically unsaturated silicone-containing monomer.

27. The hydrogel of claim 26, wherein m+n+p of said polysiloxane prepolymer is within the range of 25 to 50.

28. The hydrogel of claim 27, wherein m+n+p of said polysiloxane prepolymer is about 25.

29. The hydrogel of claim 26, wherein said polysiloxane prepolymer is endcapped within the range of 1 to 70 mole % trimethylsilyl.

30. The hydrogel of claim 29, wherein said prepolymer is endcapped within the range of 25 to 50 mole % trimethylsilyl.

31. The hydrogel of claim 30, wherein said prepolymer is endcapped within the range of 40 to 50 mole % trimethylsilyl.

32. The hydrogel of claim 26, wherein m+n+p of said polysiloxane prepolymer is about 25 and endcapped with about 50 mole % trimethylsilyl.

33. The hydrogel of claim 26, wherein T₂ is hexamethyl disiloxane.

34. The hydrogel of claim 26, wherein said hydrophilic monomer is an acrylic-containing monomer.

35. The hydrogel of claim 34, wherein said hydrophilic monomer is N,N-dimethyl acrylamide.

36. The hydrogel of claim 26, wherein said hydrophilic monomer is a vinyl-containing monomer.

37. The hydrogel of claim 36, wherein said hydrophilic monomer is N-vinyl pyrrolidone.

38. The hydrogel of claim 26, wherein said monofunctional, ethylenically unsaturated silicone-containing monomer is represented by the formula:

39. The hydrogel of claim 26, wherein the monomer mixture further comprises a UV initiator.

40. The hydrogel of claim 39, wherein said UV initiator is Darocur 1173.

41. The hydrogel of claim 26, wherein the monomer mixture further comprises a diluent.

42. The hydrogel of claim 41, wherein the diluent is hexanol.

43. A contact lens comprising the hydrogel of claim 26.

44. An intraocular lens comprising the hydrogel of claim 26.