Process for making ophthalmic lenses

• US 20070222094A1
• Filed: 03/23/2006
• Published: 09/27/2007
• Est. Priority Date: 03/23/2006
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Turner, David, Mahadevan, Shivkumar, Alli, Azaam, Zanini, Diana, Ford, James, Canavan, Kristy
• Granted Patent: US 8,414,804 B2
• Time in Patent Office: Days
• US Class Current: 264/1.320
• CPC Class Codes: B29D 11/00067 Hydrating contact lenses
• CPC Class Codes: B29D 11/0025 Removing impurities from contact lenses, e.g. leaching
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to aqueous processes for the production of silicone hydrogel contact lenses.

Claims

1. A process comprising

(a) curing in a mold a reaction mixture comprising at least one silicone containing component wherein said reaction mixture is substantially free from sparingly water soluble components or impurities having a retention time, relative to TRIS of less than about 0.9 to form a lens;

(b) contacting said lens and mold with an aqueous solution at a temperature less than 99°

C. for less than about 1 hour;

to release said lens from the mold and

(c) optionally post processing the lens, wherein said post processing, if conducted, is conducted with aqueous solutions for a time less than 6 hours.

2. The process of claim 1 wherein said reaction mixture further comprises at least one hydrophilic component.

3. The process of claim 2 wherein said hydrophilic component comprises at least one acrylic- or vinyl-containing monomer.

4. The process of claim 2 wherein said hydrophilic component comprises at least one monomer selected from the group consisting of DMA, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinyl pyrrolidone, N-vinyl-N-methyl acrylamide, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid and combinations thereof.

5. The process of claim 1 wherein said aqueous processing time is less than about 4 hours.

6. The process of claim 1 wherein said aqueous processing time is less than about 2 hours.

7. The process of claim 1 wherein said aqueous processing time is less than about one hour.

8. The process of claim 1 wherein said component or impurity is present in an amount of less than about 3000 ppm in the reaction mixture.

9. The process of claim 1 wherein said component or impurity is present in an amount of less than about 1000 ppm in the reaction mixture.

10. The process of claim 1 wherein said component or impurity is present in an amount of less than about 200 ppm based upon all components in the reaction mixture.

11. The process of claim 1 wherein said component or impurity is present in an amount of less than about 100 ppm based upon all components in the reaction mixture.

12. The process of claim 1 wherein said component or impurity has a retention time relative to TRIS of less than about 0.8.

13. The process of claim 1 wherein said at least one silicone component is selected from the group consisting of silicone containing monomers, prepolymers, macromers and mixtures thereof.

14. The process of claim 1 wherein said at least one silicone component comprises at least one silicone monomer.

15. The process of claim 1 wherein said reactive mixture is a substantially homogeneous mixture.

16. The process of claim 1 wherein said silicone component is present in said reactive mixture in an amount between about 20 and 70 weight %.

17. The process of claim 2 wherein said hydrophilic component is present in said reactive mixture in an amount up to about 50 weight %.

18. The process of claim 2 wherein said hydrophilic component is present in said reactive mixture in an amount between about 5 and about 50 weight %.

19. The process of claim 1 wherein said silicone component comprises at least one polymerizable functional group selected from the group consisting of acrylate, methacrylate, acrylamide, methacrylamide, N-vinyl lactam, N-vinylamide, and styryl functional groups.

20. The process of claim 1 wherein said silicone component comprises at least one monofunctional silicone containing component.

21. The process of claim 1 wherein said reaction mixture is free from measurable amounts of sparing water soluble components or impurities having a retention time, relative to TRIS of less than about 0.9.

22. The process of claim 1 wherein said aqueous solution further comprises at least one release aid.

23. A contact lens made by the process of claim 1.

24. A process for producing an ophthalmic lens which does not cause ocular discomfort when worn by a human comprising the steps of

(a) curing in a mold a silicone containing reaction mixture comprising less than about 3000 ppm of any sparingly water soluble component or impurity having a retention time, relative to TRIS of less than about 0.9 minutes to form said ophthalmic lens;

b) contacting said lens and mold with an aqueous solution at a temperature less than 99°

C. for less than about 1 hour;

to release said lens from the mold and

(c) optionally post processing the lens, wherein said post processing, if conducted, is conducted with aqueous solutions for a time less than 6 hours.

25. A process comprising

(a) curing in a mold a reaction mixture comprising at least one silicone containing component, and at least one sparingly water soluble component or impurity having a retention time, relative to TRIS of less than about 0.9 to produce a cured contact lens having less than an ocular discomfort causing amount of said component or impurity,

(b) contacting said lens and mold with an aqueous solution at a temperature less than 99°

C. for less than about 1 hour;

to release said lens from the mold and

(c) optionally post processing the lens, wherein said post processing, if conducted, is conducted with aqueous solutions for a time less than 6 hours.

26. The process of claim 25 wherein said reaction mixture further comprises at least one hydrophilic component.

27. The process of claim 26 wherein said hydrophilic component comprises at least one acrylic- or vinyl-containing monomer.

28. The process of claim 26 wherein said hydrophilic component comprises at least one monomer selected from the group consisting of DMA, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinyl pyrrolidone, N-vinyl-N-methyl acrylamide, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid and combinations thereof.

29. The process of claim 25 wherein said aqueous processing time is less than about 4 hours.

30. The process of claim 25 wherein said aqueous processing time is less than about 2 hours.

31. The process of claim 25 wherein said aqueous processing time is less than about one hour.

32. The process of claim 25 wherein said at least one sparingly water soluble component or impurity is present in said lens after step b, in an amount less than about 2000 ppm based upon weight of said lens in a fully hydrated state.

33. The process of claim 25 wherein said aqueous solution further comprises at least one release aid.

34. The process of claim 25 wherein said sparingly water soluble component or impurity is present in said lens after step b, in an amount of less than about 1000 ppm based upon weight of said lens in a fully hydrated state.

35. The process of claim 25 wherein said sparingly water soluble component or impurity is present in said lens after step b, in an amount of less than about 200 ppm based upon weight of said lens in a fully hydrated state.

36. The process of claim 25 wherein said sparingly water soluble component or impurity is present in said lens after step b in an amount of less than about 100 ppm based upon weight of said lens in a fully hydrated state.

37. The process of claim 25 wherein said component or impurity has a retention time relative to TRIS of less than about 0.8.

38. The process of claim 25 wherein said at least one silicone component is selected from the group consisting of silicone containing monomers, prepolymers, macromers and mixtures thereof.

39. The process of claim 25 wherein said at least one silicone component comprises at least one silicone monomer.

40. The process of claim 25 wherein said reactive mixture is a substantially homogeneous mixture.

41. The process of claim 25 wherein said silicone component is present in said reactive mixture in an amount between about 20 and 70 weight %.

42. The process of claim 26 wherein said hydrophilic component is present in said reactive mixture in an amount up to about 50 weight %.

43. The process of claim 26 wherein said hydrophilic component is present in said reactive mixture in an amount between about 5 and about 50 weight %.

44. The process of claim 25 wherein said silicone component comprises at least one polymerizable functional group selected from the group consisting of acrylate, methacrylate, acrylamide, methacrylamide, N-vinyl lactam, N-vinylamide, and styryl functional groups.

45. The process of claim 25 wherein said silicone component comprises at least one monofunctional silicone containing component.

46. A contact lens made by the process of claim 25.

47. A process comprising

(a) curing in a mold a silicone containing reaction mixture wherein all reaction mixture components and impurities which are sparingly water soluble have a retention time, relative to TRIS of at least about 1 to form a lens;

(b) contacting said lens and mold with an aqueous solution at a temperature less than 99°

C. for less than about 1 hour;

to release said lens from the mold and

(c) optionally post processing the lens, wherein said post processing, if conducted, is conducted with aqueous solutions for a time less than 6 hours.