Extended wear ophthalmic lens

• US 5,760,100 A
• Filed: 12/08/1995
• Issued: 06/02/1998
• Est. Priority Date: 09/06/1994
• Status: Expired due to Term

• Current Assignee: Novartis Ag
• Original Assignee: CIBA Vision Corporation (Bayer AG), Commonwealth Scientific & Industrial Research Organisation (Commonwealth Of Australia As Represented By Department Of Industry, Innovation, Climate Change, Science, Research And Tertiary Education)
• Inventors: Court, John, Winterton, Lynn Cook, Ho, Arthur, Lohmann, Dieter, Chabrecek, Peter, Liu, Qin, Riffle, Judy Smith, Papaspiliotopoulos, Eric, Meijs, Gordon Francis, Schindhelm, Klaus, Laycock, Bronwyn Glenice, Domschke, Angelika, Nicolson, Paul Clement, Baron, Richard Carlton, Sweeney, Deborah, Terry, Wilson Leonard Jr., Hopken, Jens, Griesser, Hans Jorg, Vogt, Jurgen
• Primary Examiner(s): MERRIAM, ANDREW EDWIN
• Application Number:
  US08/569,816
• Time in Patent Office: 907 Days
• Field of Search: 523/106, 525/903, 525/936, 525/101, 351/160 H
• US Class Current: 523/106
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: B05D 1/62 Plasma-deposition of organic layers plasma deposition in general C23C14/00, C23C16/00
• CPC Class Codes: B29C 39/42 Casting under special conditions, e.g. vacuum
• CPC Class Codes: B29C 71/00 After-treatment of articles without altering their shape; Apparatus therefor B29C44/56, B29C73/00 take precedence; surface shaping B29C59/00 ; for joined or sealed parts B29C66/03; after-treatment specially adapted for vulcanising tyres B29D30/0633
• CPC Class Codes: B29D 11/00076 enabling passage of fluids, e.g. oxygen, tears, between the area under the lens and the lens exterior
• CPC Class Codes: B29L 2011/0041 Contact lenses
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/5015 having fluorine atoms
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/63 Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/8116 esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• CPC Class Codes: C08G 18/8175 with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• 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
• CPC Class Codes: Y10S 525/903 : Interpenetrating network
• CPC Class Codes: Y10S 525/936 : Encapsulated chemical agent
• CPC Class Codes: Y10S 525/937 : Utility as body contact e.g. implant, contact lens or I.U.D.

Abstract

An ophthalmic lens suited for extended-wear for periods of at least one day on the eye without a clinically significant amount of corneal swelling and without substantial wearer discomfort. The lens has a balance of oxygen permeability and ion or water permeability, with the ion or water permeability being sufficient to provide good on-eye movement, such that a good tear exchange occurs between the lens and the eye. A preferred lens is a copolymerization product of a oxyperm macromer and an ionoperm monomer. The invention encompasses extended wear contact lenses, which include a core having oxygen transmission and ion transmission pathways extending from the inner surface to the outer surface.

Claims

1. An ophthalmic lens having ophthalnically compatible inner and outer surfaces, said lens being suited to extended periods of wear in continuous, intimate contact with ocular tissue and ocular fluids, said lens comprising a polymeric material which has a high oxygen permeability and a high ion permeability, said polymeric material being formed from polymerizable materials comprising:

(a) at least one oxyperm polymerizable material and

(b) at least one ionoperm polymerizable material,

wherein said lens allows oxygen permeation in an amount sufficient to maintain corneal health and wearer comfort during a period of extended, continuous contact with ocular tissue and ocular fluids,

wherein said oxyperm polymerizablea material forms a phase or phases substantially seperate from the phase or phases formed by said ionoperm polymerizable material,

wherein said lens allows ion or water permeation via ion or water pathways in an amount sufficient to enable the lens to move on the eye such that corneal health is not substantially hared and wearer comfort is acceptable during a period of extended, continuous contact with ocular tissue and ocular fluids,

wherein said ionoperm polyrnerizable material, if polymerized alone would form a hydrophilic polymer having a water content of atleast 10 weight percent upon full hydration, and

wherein said ophthalmic lens has an oxygen transmissibility of at least about 70 barrers/mm and an ion permeability characteized either by (1) an Ionoton Ion Permeability Coefficient of greater than about 0.2×

10^-6 cm² /sec. or(2) an Ionoflux Diffusion Coefficient of greater than about 1.5×

10³¹ 6 mm² /min. wherein said ion permeability is measured with respect to sodium ions.

2. An ophthalmic lens of claim 1, wherein said ophthalmic lens is selected from the group consisting of contact lenses for vision correction, contact lenses for eye color modification, ophthalmic drug delivery devices, and ophthalmic wound healing devices.

3. An ophthalmic lens of claim 2, wherein said ophthalmic lens is a contact lens.

4. An ophthalmic lens of claim 1, wherein said ophthalmic lens has an oxygen transmissibility of at least about 75 barrers/mm.

5. An ophthalmic lens of claim 4, wherein said ophthalmic lens has an oxygen transmissibility of at least about 87 barrers/mm.

6. An ophthalmic lens of claim 1, wherein said polymeric material comprises an ionoperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens.

7. An ophthalmic lens of claim 1, wherein said polymeric material comprises an oxyperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens.

8. An ophthalmic lens of claim 1, wherein said polymeric material comprises a plurality of co-continuous phases, including at least one oxyperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens and at least one ionoperm phase which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens.

9. An ophthalmic lens of claim 1, wherein said polymeric material comprises at least one ion or water pathway which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens.

10. An ophthalmic lens of claim 1, wherein said polymeric material comprises at least one oxygen pathway which extends continuously from the inner surface of the ophthalmic lens to the outer surface of the ophthalmic lens.

11. An ophthalmic lens of claim 1, wherein said polymeric material comprises a plurality of co-continuous pathways, at least one being an ion or water pathway and at least one other being an oxygen pathway, which pathways extend continuously from the inner surface of the lens to the outer surface of the lens.

12. An ophthalmic lens of claim 11, wherein said co-continuous pathways include a continuous phase of ionoperm polymeric material and a continuous phase of siloxane-containing polymeric material.

13. An ophthalmic lens of claim 11, wherein said pathways have a domain size which is less than a size which undesirably distorts visible light in an amount which is visible to the eye of the wearer.

14. An ophthalmic lens of claim 1, wherein said lens has an Ionoton Ion Permeability Coefficient of greater than about 0.3×

10^-6 cm² /sec and wherein said Ionoton Ion Permeability Coefficient is measured with respect to sodium ions.

15. An ophthalmic lens of claim 14, wherein said lens has an Ionoton Ion Permeability Coefficient of greater than about 0.4×

10^-6 cm² /sec and wherein said Ionoton Ion Permeability Coefficient is measured with respect to sodium ions.

16. An ophthalmic lens of claim 1, wherein said lens has an Ionoflux Diffusion Coefficient of greater than about 2.6×

10^-6 mm² /min and wherein said Ionoflux Ion Permeability Coefficeint is measured with respect to sodium ions.

17. An ophthalmic lens of claim 16, wherein said lens has an Ionoflux Diffuision Coefficient of greater than about 6.4×

10^-6 mm² /min and wherein said Ionoflux Ion Permeability Coefficient is measured with respect to sodium ions.

18. An ophthalmic lens of claim 1, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.2×

10^-6 cm² /sec.

19. An ophthalmic lens of claim 18, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.3×

10^-6 cm² /sec.

20. An ophthalmic lens of claim 19, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.4×

10^-6 cm² /sec.

21. An ophthalmic lens of claim 1, wherein when hydrated, said lens has an equilibrium water content of less than about 32 weight percent when tested in accordance with the Bulk Technique.

22. An ophthalmic lens of claim 21, wherein when hydrated, said lens has an equilibrium water content of about 10 to about 30 weight percent when tested in accordance with the Bulk Technique.

23. An ophthalmic lens of claim 22, wherein when hydrated, said lens has an equilibrium water content of about 15 to about 25 weight percent when tested in accordance with the Bulk Technique.

24. An ophthalmic lens of claim 1, wherein said polymeric material is formed from a polymerizable mixture comprising:

(a) about 60 to about 85 weight percent oxyperm macromer; and

(b) about 15 to about 40 weight percent ionoperm monomer.

25. An ophthalmic lens of claim 24, wherein said polymeric material is formed from a polymerizable mixture comprising:

(a) about 70 to about 82 weight percent oxyperm macromer; and

(b) about 18 to about 30 weight percent ionoperm monomer.

26. An ophthlamic lens of claim 1, wherein said lens allows oxygen transmission in an amount sufficient to prevent any clinically signficant corneal swelling during a period of extended, continuous contact with ocular tissue and ocular fluids.

27. An ophthalmic lens of claim 1, wherein said lens produces, after wear of about 24 hours, including normal sleep periods, less than about 8% corneal swelling.

28. An ophthalmic lens of claim 27, wherein said lens produces, after wear of about 24 hours, including normal sleep periods, less than about 6% corneal swelling.

29. An ophthalmic lens of claim 28, wherein said lens produces, after wear of about 24 hours, including normal sleep periods, less than about 4% corneal swelling.

30. An ophthalmic lens of claim 1, wherein said period of extended continuous contact is at least 24 hours.

31. An ophthalmic lens of claim 30, wherein said period of extended continuous contact is at least 4 days.

32. An ophthalmic lens of claim 31, wherein said period of extended continuous contact is at least 7 days.

33. An ophthalmic lens of claim 32, wherein said period of extended continuous contact is at least 14 days.

34. An ophthalmic lens of claim 33, wherein said period of extended continuous contact is at least 30 days.

35. An ophthalmic lens of claim 1, wherein said lens has a tensile modulus of 3 MPa or less.

36. An ophthalmic lens of claim 1, wherein said lens has a short relaxation time constant of greater than about 3.5 seconds, wherein said short relaxation time constant is measured in phosphate-buffered saline solution.

37. An ophthalmic lens of claim 26, wherein said lens has an Ionoton Ion Permeability Coefficient, P, of greater than about 0.2×

10^-6 cm² /sec, wherein said short relaxation time constant is measured in phosphate-buffered saline solution and wherein said Ionoton Ion Permeability Coefficient is measured with respect to sodium ions.

38. An ophthalmic lens of claim 26, wherein said lens has an Ionoflux Diffusion Coefficient of greater than about 2.6×

10^-6 mm² /min, wherein said short relaxation time constant is measured in phosphate-buffered saline solution and wherein said Ionoton Ion Permeability Coefficient is measured with respect to sodium ions.

39. An ophthalmic lens of claim 36, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.2×

10^-6 cm² /min, wherein said short relaxation time constant is measured in phosphate-buffered saline solution.

40. An ophthalmic lens of claim 1, wherein the polymeric material has a tan δ

above about 0.25 at about 10 Hz, wherein said short relaxation time constant is measured in phosphate-buffered saline solution.

41. An ophthalmic lens of claim 1, wherein said lens has an Ionoton Ion Permeability Coefficient of greater than about 0.3×

10^-6 cm² /sec, a tensile modulus of 3 MPa or less, and a short relaxation time constant of greater than about 3.5 seconds, wherein said short relaxation time constant is measured in phosphate-buffered saline solution and wherein said Ionoton Ion Permeability Coefficient is measured with respect to sodium ions.

42. An ophthalmic lens of claim 1, wherein said lens has an Ionoflux Diffusion Coefficient of greater than about 2.6×

10^-6 mm² /min., a tensile modulus of 3 MPa or less, and a short relaxation time constant of greater than about 3.5 seconds, wherein said short relaxation time constant is measured in phosphate-buffered saline solution and wherein said Ionoflux Ion Permeability Coefficient is measured with respect to sodium ions.

43. An ophthalmic lens of claim 1, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.3×

10^-6 cm² /min., a tensile modulus of 3 MPa or less, and a short relaxation time constant of greater than about 3.5 seconds, wherein said short relaxation time constant is measured in phosphate-buffered saline solution.

44. An ophthalmic lens having ophthalmically compatible inner and outer surfaces, said lens being suited to extended periods of wear in continuous, intimate contact with ocular tissue and ocular fluids, said lens comprising a polymeric material which has a high oxygen permeability and a high ion permeability, said polymeric material being formed from polymerizable materials comprising at least one polymerizable material comprising:

(a) at least one oxyperm segment; and

(b) at least one ionoperm segment,

wherein said lens allows oxygen permeation in an amount sufficient to maintain corneal health and wearer comfort during a period of extended, continuous contact with ocular tissue and ocular fluids,

wherein said oxyperm polymerizable mateerial forms a phase or phases substantially separate from the phase of phase formed by said ionoperm polymerizable material,

wherein said lens allows ion or water permeation via ion or water pathways in an amount sufficient to enable the lens to move on the eye such that corneal health is not substantially harmed and wearer comfort is acceptable during a period of extended, continuous contact with ocular tissue and ocular fluids,

Wherein said ionoperm polymerizable material, if polymerized alone, would form a hydrophilic polymer having a water content of at least 10 weight percent upon full hydration, and

Wherein said ophthalmic lens has an oxygen transmissibility of at least about 70 barrers/mm and an ion permeability characterized either by (1) an Ionoton Ion Permeability Coeffecient of greater than about0.2×

10³¹ 6 cm² /sec. or (2) an Ionoflux Diffusion Coefficient of greater than about 1.5×

10^-6 mm² min. Wherein said ion permeability is measured with respect to sodiumn ions.

45. An ophthalmic lens of claim 44, wherein said ophthalmic lens has an oxygen transmissibility of at least about 75 barrers/mm.

46. An ophthalmic lens of claim 45, wherein said ophthalmic lens has an oxygen transmissibility of at least about 87 barrers/mm.

47. An ophthalmic lens of claim 44, wherein said lens has an Ionoflux Diffusion Coefficient of greater than about 1.5×

10^-6 mm² /min and wherein said Ionoflux Ion Pemeability Coefficient is measured with respect to sodium ions.

48. An ophthalmic lens of claim 44, wherein said lens has a Hydrodell Water Permeability Coefficient of greater than about 0.2×

10^-6 cm² /sec.