Wettable silicone hydrogel contact lenses and related compositions and methods

• US 8,231,218 B2
• Filed: 06/11/2007
• Issued: 07/31/2012
• Est. Priority Date: 06/15/2006
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Hong, Ye, Chen, Charlie, Manesis, Nick
• Primary Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US11/761,332
• Publication Number:
  US 20070296914A1
• Time in Patent Office: 1,877 Days
• Field of Search: 523/106, 523/107, 351/160.H, 351/160.R, 623/6.56, 623/6.6, 424/429, 526/279, 524/865
• US Class Current: 351/160.H
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• 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: B29K 2039/06 Polymers of N-vinyl-pyrrolidones
• CPC Class Codes: B29K 2077/00 Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
• CPC Class Codes: B29K 2083/00 Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
• CPC Class Codes: B29K 2105/0061 Gel or sol
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

Silicone hydrogel contact lenses having ophthalmically acceptable surface wettabilities are obtained from pre-extracted polymerized silicone hydrogel contact lens products having relatively large amounts of removable or extractable materials. The silicone hydrogel contact lenses can be obtained from non-polar resin based contact lens molds and without surface treatments or an interpenetrating polymeric network of a polymeric wetting agent. Related lens products, polymerizable compositions, and methods are also described.

Claims

1. A polymerizable silicone hydrogel contact lens precursor composition, comprising:

a polymerizable non-silicon-containing component combined with a polymerizable silicon-containing component as a polymerizable silicone hydrogel contact lens precursor composition, a portion of the polymerizable silicone hydrogel contact lens precursor composition being removable from a polymerized silicone hydrogel contact lens product produced from the polymerizable silicone hydrogel contact lens precursor composition, and being present in an amount of at least 10% (w/w) of the polymerized silicone hydrogel contact lens product, wherein said portion has unreacted monomer, partially reacted monomer, or both in an amount that is at least 10% (w/w) based on the weight of the polymerized silicone hydrogel contact lens product.

2. The polymerizable silicone hydrogel contact lens precursor composition of claim 1, wherein the polymerizable non-silicon-containing component comprises a first monomer having a first reactivity ratio, and a second monomer having a second reactivity ratio less than the first reactivity ratio.

3. The polymerizable silicone hydrogel contact lens precursor composition of claim 2, wherein the polymerizable non-silicon-containing component further comprises a cross-linking agent having a reactivity ratio similar to the first reactivity ratio.

4. The polymerizable silicone hydrogel contact lens precursor composition of claim 1, wherein the polymerizable silicon-containing component is α

-ω

-Bis(methacryloyloxyethyl iminocarboxy ethyloxypropyl)-poly(dimethylsiloxane)-poly (trifluoropropylmethylsiloxane)-poly(ω

-methoxy-poly(ethyleneglycol)propylmethylsiloxane);

dimethacryloyl silicone-containing macromer, and the polymerizable non-silicon-containing component comprises N-vinyl-N-methylacetamide, methyl methacrylate, tri(ethylene glycol) dimethacrylate, and an initiator.

5. The polymerizable silicone hydrogel contact lens precursor composition of claim 4, wherein the non-silicon-containing component further comprises an ultraviolet absorber and a tinting agent.

6. The polymerizable silicone hydrogel contact lens precursor composition of claim 5, further comprising a block copolymer of polydimethylsiloxane and polyethylene glycol.

7. The polymerizable silicone hydrogel contact lens precursor composition of claim 1, wherein the polymerizable silicon-containing component is α

-ω

-Bis(methacryloyloxyethyl iminocarboxy ethyloxypropyl)-poly(dimethylsiloxane)-poly(trifluoropropylmethylsiloxane)-poly(ω

-methoxy-poly(ethyleneglycol)propylmethylsiloxane);

dimethacryloyl silicone-containing macromer, and the polymerizable non-silicon-containing component comprises 1-vinyl-2-pyrrolidone, methyl methacrylate, tri(ethylene glycol)dimethacrylate, and an initiator.

8. The polymerizable silicone hydrogel contact lens precursor composition of claim 7, wherein the non-silicon-containing component further comprises decanol.

9. The polymerizable silicone hydrogel contact lens precursor composition of claim 8, wherein the decanol is present in an amount from about 5% (w/w) to about 30% (w/w) of the composition.

10. The polymerizable silicone hydrogel contact lens precursor composition of claim 7, further comprising a block copolymer of polydimethylsiloxane and polyethylene glycol.

11. The polymerizable silicone hydrogel contact lens precursor composition of claim 7, further comprising a hydrophilic silicone-containing demolding aid or a polyalkylene oxide demolding aid.

12. The polymerizable silicone hydrogel contact lens precursor composition of claim 7, wherein the non-silicon-containing component further comprises a diluent selected from the group consisting of hexanol, ethoxyethanol, isopropanol, propanol, decanol, and combinations thereof.

13. The polymerizable silicone hydrogel contact lens precursor composition of claim 12, further comprising units of a methacrylate phosphorylcholine-monomer.

14. The polymerizable silicone hydrogel contact lens precursor composition of claim 1, further comprising an extractable hydrophobic additive or an extractable amphiphilic additive.

15. The polymerizable silicone hydrogel contact lens precursor composition of claim 14, wherein the additive is ethylene glycol stearate, diethylene glycol monolaurate, a C₂-C₂₄ alcohol, a C₂-C₂₄ amine, or polydimethylsiloxane co-PEG, or combinations thereof.

16. The polymerizable silicone hydrogel contact lens precursor composition of claim 15, wherein the additive is decanol, or polydimethylsiloxane-co-PEG, or combinations thereof.

17. The polymerizable silicone hydrogel contact lens precursor composition of claim 16, wherein the additive comprises polydimethylsiloxane-co-PEG having a molecular weight in a range of about 300 to about 30,000 Daltons.

18. The polymerizable silicone hydrogel contact lens precursor composition of claim 16, wherein the additive comprises polydimethylsiloxane-co-PEG having a molecular weight of less than about 3,000 Daltons.

19. The polymerizable silicone hydrogel contact lens precursor composition of claim 14, wherein the additive is present in an amount in a range of about 1% to about 60% (w/w) of the composition.

20. The polymerizable silicone hydrogel contact lens precursor composition of claim 14, comprising at least two different additives.

21. The polymerizable silicone hydrogel contact lens precursor of claim 1, wherein the polymerizable silicone hydrogel contact lens precursor composition comprises at least two reactive components that comprise monomer types with different reactivity ratios.

22. The polymerizable silicone hydrogel contact lens precursor composition of claim 1, wherein the polymerizable non-silicon-containing component comprises a hydrophilic vinyl-containing monomer.

23. The polymerizable silicone hydrogel contact lens precursor composition of claim 1, wherein the portion of the polymerizable silicone hydrogel contact lens precursor composition being removable from a polymerized silicone hydrogel contact lens product produced from the polymerizable silicone hydrogel contact lens precursor composition is present in an amount of at least 15% (w/w) of the polymerized silicone hydrogel contact lens product, and said portion has unreacted monomer, partially reacted monomer, or both in an amount that is at least 15% (w/w) based on the weight of the polymerized silicone hydrogel contact lens product.

24. A silicone hydrogel contact lens, comprising:

a lens body comprising a silicone hydrogel material, the lens body having an ophthalmically acceptable surface wettability and a dry weight no greater than 90% of the dry weight of the lens body prior to extraction, wherein said lens body had at least 15% (w/w) extractables removed by extraction based on the dry weight of the lens body prior to extraction, and said extractables have unreacted monomer, partially reacted monomer, or both, in an amount that is at least 15% (w/w/) based on the dry weight of the lens body prior to extraction, and wherein the lens body is a cast molded element obtained from a non-polar resin contact lens mold.

25. The silicone hydrogel contact lens of claim 24, wherein the lens body is free of a surface treatment that provides an ophthalmically acceptable surface wettability.

26. The silicone hydrogel contact lens of claim 24, wherein the lens body is free of an interpenetrating polymer network of a polymeric wetting agent that provides an ophthalmically acceptable surface wettability.

27. The silicone hydrogel contact lens of claim 24, wherein the lens body is hydrated and comprises an advancing contact angle less than about 120 degrees, a tensile modulus less than about 1.6 MPa, an ionoflux less than about 7 10⁻

3 mm²/min, an oxygen permeability of at least about 70 barrers, or a water content of at least about 30% by weight, or combinations thereof.

28. The silicone hydrogel contact lens of claim 24, wherein the lens body comprises units obtained from a methacrylate phosphorylcholine-monomer.

29. The silicone hydrogel contact lens of claim 28, wherein the lens body comprises units obtained from 2-methacryloyloxyethyl phosphorylcholine.

30. The silicone hydrogel contact lens of claim 24, wherein the lens body has an equilibrium water content from about 35% to about 65%.

31. The silicone hydrogel contact lens of claim 24, wherein said lens body is a polymerization product of a polymerizable composition comprising at least two reactive components that comprise monomer types with different reactivity ratios.

32. The silicone hydrogel contact lens of claim 24, wherein said extraction is achieved with a liquid extraction media that is an alcohol.

33. The silicone hydrogel contact lens of claim 24, wherein said extraction is achieved with a liquid extraction media that is chloroform.

34. The silicone hydrogel contact lens of claim 24, wherein said silicone hydrogel material comprises a hydrophilic vinyl-containing monomer.

35. A silicone hydrogel contact lens, comprising:

a lens body comprising a silicone hydrogel material, the lens body having an ophthalmically acceptable surface wettability and a dry weight no greater than 90% of the dry weight of the lens body prior to extraction, wherein said lens body had at least 10% (w/w) extractables removed by extraction based on the dry weight of the lens body prior to extraction, and said extractables have unreacted monomer, partially reacted monomer, or both, in an amount that is at least 10% (w/w/) based on the dry weight of the lens body prior to extraction, and wherein the lens body is a cast molded element obtained from a non-polar resin contact lens mold, wherein said silicone hydrogel material comprises a hydrophilic vinyl-containing monomer.

36. The polymerized silicone hydrogel contact lens product of claim 35, wherein the pre-extracted body member has a removable component content from 10% (w/w) to about 75% (w/w) of the body member.

37. The silicone hydrogel contact lens of claim 35, wherein the lens body has an equilibrium water content from about 35% to about 65%.

38. The silicone hydrogel contact lens of claim 35, wherein the lens body is a polymerization product of a polymerizable composition comprising at least two reactive components that comprise monomer types with different reactivity ratios.

39. The silicone hydrogel contact lens of claim 35, wherein the lens body is free of a surface treatment that provides an ophthalmically acceptable surface wettability.

40. The silicone hydrogel contact lens of claim 35, wherein the lens body is free of an interpenetrating polymer network of a polymeric wetting agent that provides an ophthalmically acceptable surface wettability.

41. The silicone hydrogel contact lens of claim 35, wherein the lens body is hydrated and comprises an advancing contact angle less than about 120 degrees, a tensile modulus less than about 1.6 MPa, an ionoflux less than about 7 10⁻

3 mm²/min, an oxygen permeability of at least about 70 barrers, or a water content of at least about 30% by weight, or combinations thereof.

42. The silicone hydrogel contact lens of claim 35, wherein said extraction is achieved with a liquid extraction media that is an alcohol.

43. The silicone hydrogel contact lens of claim 35, wherein said extraction is achieved with a liquid extraction media that is chloroform.

44. The silicone hydrogel contact lens of claim 35, wherein the lens body comprises units obtained from a methacrylate phosphorylcholine-monomer.

45. The silicone hydrogel contact lens of claim 44, wherein the lens body comprises units obtained from 2-methacryloyloxyethyl phosphorylcholine.

46. A pre-extracted polymerized silicone hydrogel contact lens product, comprising:

a pre-extracted body member having a dry weight at least 10% greater than the dry weight of the body member after subjecting the body member to an extraction procedure to form an extracted polymerized silicone hydrogel contact lens product, wherein said pre-extracted body member has at least 10% (w/w) extractables removable by extraction based on the dry weight of the body member prior to extraction, and said extractables have unreacted monomer, partially reacted monomer, or both in an amount that is at least 10% (w/w/) based on the dry weight of the body member prior to extraction, and wherein the pre-extracted body member is a cast molded element obtained from a non-polar resin contact lens mold, wherein said pre-extracted body member is a polymerization product of a polymerizable composition comprising at least two reactive components that comprise monomer types with different reactivity ratios.

47. A method for producing a silicone hydrogel contact lens, comprising:

forming a silicone hydrogel contact lens body having a dry weight no greater than 90% of the dry weight of the lens body prior to extraction and an ophthalmically acceptable surface wettability from a pre-extracted silicone hydrogel contact lens product having a removable component content of at least 10% (w/w) of the lens product, wherein said removable component content has unreacted monomer, partially reacted monomer, or both in an amount that is at least 10% (w/w) based on the dry weight of the silicone hydrogel contact lens body, and wherein the lens body is a cast molded element obtained from a non-polar resin contact lens mold.

48. The method of claim 47, wherein the forming comprises extracting extractables from the pre-extracted silicone hydrogel contact lens product.

49. The method of claim 47, further comprising curing a polymerizable silicone hydrogel contact lens precursor composition to form a pre-extracted polymerized silicone hydrogel contact lens product having a removable component content of at least 10% (w/w) of the lens product.

50. The method of claim 49, further comprising adding a removable additive to the polymerizable silicone hydrogel contact lens precursor composition.

51. The method of claim 50, wherein the removable additive is selected from the group consisting of compatibilizers, demolding aids, delensing aids, wettability enhancers, modulus reducers, ionoflux reducers, and combinations thereof.

52. The method of claim 49, further comprising adding an agent selected from the group consisting of an ultraviolet absorber, a tinting agent, and combinations thereof, to the lens precursor composition.

53. The method of claim 49, wherein the polymerizable silicone hydrogel contact lens precursor composition comprises a hydrophilic vinyl-containing monomer.

54. The method of claim 47, wherein the silicone hydrogel contact lens is produced without surface treating the lens or forming the lens with an interpenetrating polymer network of a polymeric wetting agent.

55. The method of claim 47, wherein said silicone hydrogel contact lens is a polymerization product of a polymerizable composition comprising at least two reactive components that comprise monomer types with different reactivity ratios.

56. The method of claim 47, wherein the pre-extracted silicone hydrogel contact lens product has a removable component content of at least 15% (w/w) of the lens product, and said removable component content has unreacted monomer, partially reacted monomer, or both in an amount that is at least 15% (w/w) based on the dry weight of the silicone hydrogel contact lens body.