CONTACT LENS WITH A HYDROPHILIC LAYER

• US 20160320635A1
• Filed: 07/08/2016
• Published: 11/03/2016
• Est. Priority Date: 08/27/2012
• Status: Active Grant

• Current Assignee: Tangible Science, Llc
• Original Assignee: Andrew A. Mcgibbon, Douglas M. Ackermann, Evan S. Luxon, Karen L. Havenstrite, Paul A. Cook
• Inventors: MCCRAY, Victor W., FELKINS, Brandon M., ACKERMANN, Douglas M., SMITH, Garrett C., MCGIBBON, Andrew A., HAVENSTRITE, Karen L., COOK, Paul A., LUXON, Evan S.
• Granted Patent: US 10,451,896 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 2203/02 for biomedical use
• CPC Class Codes: C08L 2205/025 containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
• CPC Class Codes: C08L 5/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 105/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09D 171/00 Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06; Coating compositions based on derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 2202/16 Laminated or compound lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

Embodiments of the technology relate to a contact lens having a core that is covalently coated by a hydrogel layer, and to methods of making such a lens. In one aspect, embodiments provide for a coated contact lens comprising a lens core comprising an outer surface; and a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population having a first PEG species and a second PEG species, the first PEG species being at least partially cross-linked to the second PEG species.

Claims

1. A coated contact lens comprising:

a lens core comprising an outer surface; and

a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population having a first polymer species with a reactive electron pair accepting group and a second polymer species with a reactive nucleophilic group, the first polymer species being at least partially cross-linked to the second polymer species through the reactive electron pair accepting group of the first polymer species and the reactive nucleophilic group through the second polymer species.

2. The lens of claim 1, wherein the first polymer species is polyethylene glycol (PEG).

3. The lens of claim 2, wherein the second polymer species is polyethylene glycol (PEG).

4. The lens of claim 2, wherein the second polymer species is polyacrylamide (PAM).

5. The lens of claim 1, wherein the first polymer species is polyacrylamide (PAM) and the second polymer species is polyacrylamide (PAM).

6. The lens of claim 1, wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.

7. The lens of claim 1, wherein the hydrogel layer and core are covalently attached at the outer surface by a sulfonyl moiety.

8. The lens of claim 1, wherein the hydrogel layer and core are covalently attached at the outer surface by a thioether moiety.

9. The lens of claim 1, wherein the hydrogel layer and core are covalently attached at the outer surface by a sulfonyl moiety and a thioether moiety.

10. The lens of claim 1, wherein the hydrogel layer substantially surrounds the outer surface of the core.

11. The lens of claim 1, wherein the hydrogel layer and core are substantially optically clear.

12. The lens of claim 1, wherein the hydrogel layer is adapted to allow optical transmission through the hydrogel layer to the ophthalmic surface.

13. The lens of claim 1, wherein the hydrogel layer comprises a thickness between about 50 nm to about 500 nm.

14. The lens of claim 1, wherein the hydrogel layer comprises a thickness below about 100 nm.

15. The lens of claim 1, wherein each of the first polymer species and second polymer species is a branched species having a branch count between two to twelve branch arms.

16. The lens of claim 1, wherein the reactive electron pair accepting group is a sulfone moiety.

17. The lens of claim 1, wherein the reactive nucleophilic group is a thiol moiety.

18. The lens of claim 1, wherein the reactive electron pair accepting group of the first polymer species is covalently linked to the outer surface of the core.

19. The lens of claim 1, further comprising an advancing contact angle between about 20 degrees to about 50 degrees.

20. The lens of claim 1, further comprising an advancing contact angle between about 25 degrees to about 35 degrees.

21. The lens of claim 1, wherein the hydrogel layer comprises between about 80% to about 98% water by weight.

22. The lens of claim 1, wherein the core consists of silicone.

23. The lens of claim 1, wherein the core comprises silicone.

24. The lens of claim 1, wherein the core is substantially free of silicone.

25. The lens of claim 1, wherein the core comprises a hydrogel.

26. The lens of claim 1, wherein the hydrogel layer further comprises at least one active agent.

27. The lens of claim 26, wherein the at least one active agent is selected from the group consisting of a UV-absorbing agent, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, or any mixture thereof.

28. A coated contact lens comprising:

a lens core comprising an outer surface; and

a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population having a first polymer species with a reactive sulfonyl group and a second polymer species with a reactive amine group, the first polymer species being at least partially cross-linked to the second polymer species through a sulfonamide covalent linkage between the reactive sulfonyl group of the first polymer species and the reactive amine group of the second polymer species.

29. The lens of claim 28, wherein the first polymer species is polyethylene glycol (PEG).

30. The lens of claim 29, wherein the second polymer species is polyethylene glycol (PEG).

31. The lens of claim 29, wherein the second polymer species is polyacrylamide (PAM).

32. The lens of claim 28, wherein the first polymer species is polyacrylamide (PAM) and the second polymer species is polyacrylamide (PAM).

33. The lens of claim 28, wherein the hydrogel layer comprises a thickness below about 100 nm.

34. The lens of claim 28, wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.

35. The lens of claim 28, wherein the hydrogel layer further comprises at least one active agent.

36. The lens of claim 28, wherein the at least one active agent is selected from the group consisting of a UV-absorbing agent, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, or any mixture thereof.

37. The lens of claim 28, wherein the core layer consists of silicone.

38. The lens of claim 28, wherein the core layer comprises silicone.

39. The lens of claim 28, wherein the core layer is substantially free of silicone.

40. A method of making a hydrogel coated contact lens comprising:

reacting an outer surface of the contact lens with a first polymer species of a hydrophilic polymer solution, wherein the first polymer species comprises an electron pair accepting moiety and a first portion of the electron pair accepting moiety forms a covalent attachment to the outer surface of the contact lens through a first nucleophilic conjugate reaction; and

reacting the first polymer species of the hydrophilic polymer solution with a second polymer species of the hydrophilic polymer solution, the second polymer species comprising a nucleophilic reactive moiety adapted to covalently link to a second portion of the electron pair accepting moiety of the first polymer species in a second nucleophilic conjugate reaction to thereby at least partially cross-link the first polymer species and second polymer species, wherein a hydrogel coating is formed and covalently attached to the outer surface of the contact lens by the first and second nucleophilic conjugate reactions.

41. The method of claim 40, wherein the first polymer species comprises a first polyethylene glycol (PEG) species.

42. The method of claim 40, further comprising modifying an outer surface of a contact lens to form the plurality of reactive nucleophilic sites on the outer surface.

43. The method of claim 40, wherein the modifying step comprises exposing the outer surface of the contact lens to a gas plasma treatment.

44. The method of claim 40, wherein reacting an outer surface of the contact lens with the first polymer species comprises reacting at least a portion of the plurality of reactive nucleophilic sites on the outer surface with the first portion of the electron pair accepting moiety on the first polymer species.

45. The method of claim 40, wherein both of the first and second nucleophilic conjugate reactions are 1,4-nucleophilic addition reactions.

46. The method of claim 40, wherein the first and second nucleophilic conjugate reactions are both a Michael-type reaction.

47. The method of claim 40, wherein both of the first and second nucleophilic conjugate reactions are click reactions.

48. The method of claim 40, wherein the nucleophilic reactive moiety of the second polymer species is a thiol group and the electron pair accepting moiety of the first polymer species is a sulfone group.

49. The method of claim 40, wherein the first polymer species and the second polymer species are cross-linked through a thioether moiety.

50. The method of claim 40, wherein the hydrophilic polymer solution comprises substantially equivalent concentrations of the first polymer species and second polymer species.

51. The method of claim 40, wherein the concentration of the electron pair accepting moiety of the first polymer species exceeds the concentration of the nucleophilic reactive moiety of the second polymer species by about 1% to about 30%.

52. The method of claim 40, wherein the concentration of the electron pair accepting moiety of the first polymer species exceeds the concentration of the nucleophilic reactive moiety of the second polymer species by about 5% and about 20%.

53. The method of claim 40, wherein the reacting steps are performed at a temperature between about 15 degrees Celsius and about 100 degrees Celsius.

54. The method of claim 40, wherein the reacting steps are performed at a temperature between about 20 degrees Celsius and about 40 degrees Celsius.

55. The method of claim 40, wherein the reacting steps are performed at a pH between about 7 and about 11.

56. The method of claim 40, wherein the hydrogel coating is substantially optically clear.

57. The method of claim 40, wherein the contact lens comprises a core consisting of silicone.

58. The method of claim 40, wherein the contact lens comprises a core comprising silicone.

59. The method of claim 40, wherein the contact lens comprises a core substantially free of silicone.

60. The method of claim 59, wherein the contact lens comprises a hydrogel core.

61. The method of claim 41, wherein the second polymer species is polyethylene glycol (PEG) or polyacrylamide (PAM).

62. The method of claim 40, wherein the first polymer species is polyacrylamide (PAM) and the second polymer species is polyacrylamide (PAM).

63. The method of claim 40, wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.

64. A contact lens solution, the solution comprising:

a first polymer species comprising polyethylene glycol (PEG) with a reactive electron pair accepting group; and

a second polymer species comprising polyacrylamide (PAM) with a reactive nucleophilic group;

wherein the first polymer species is adapted to at least partially cross-link to the second polymer species through the reactive electron pair accepting group of the first polymer species and the reactive nucleophilic group of the second polymer species when a contact lens with a hydrophilic coating is placed in the solution.

65. The solution of claim 64, wherein the solution includes water.

66. The solution of claim 64, wherein the concentration of the first and second polymer species is each independently between about 0.01 (w/v) % and about 0.50 (w/v) %.

67. A coated contact lens comprising:

a lens core comprising an outer surface; and

a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population comprising a polyacrylamide (PAM) polymer species, wherein the hydrogel layer comprises a thickness below about 100 nm.

68. The lens of claim 67, the hydrophilic polymer population further comprising a second polymer species comprising polyethylene glycol (PEG).

69. The lens of claim 68, wherein the hydrogel layer includes cross-linking between the polyacrylamide polymer species and the second polymer species comprising PEG.

70. The lens of claim 67, wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.