CONTACT LENSES AND METHODS OF MAKING CONTACT LENSES

• US 20170160432A1
• Filed: 07/20/2015
• Published: 06/08/2017
• Est. Priority Date: 07/21/2014
• Status: Abandoned Application

• Current Assignee: Tangible Science, Llc
• Original Assignee: Tangible Science, Llc
• Inventors: HAVENSTRITE, Karen L., MCCRAY, Victor Wayne, FELKINS, Brandon McNary, MCGIBBON, Andrew A.
• Application Number:
  US15/325,678
• Publication Number:
  US 20170160432A1
• Time in Patent Office: Days
• CPC Class Codes: A61F 9/00 Methods or devices for treatment of the eyes; Devices for putting-in contact lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand caps with means for protecting the eyes A42B1/018; visors for helmets A42B3/22; retractors A61B17/02; manipulators specially adapted for use in surgery A61B34/70; appliances to aid invalids to move about A61H3/00; exercisers for the eyes A61H5/00; eye baths A61H35/02; sunglasses or goggles having the same features as spectacles G02C
• CPC Class Codes: A61F 9/0017 implantable in, or in contact with, the eye, e.g. ocular inserts
• 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: C08J 2383/04 Polysiloxanes
• CPC Class Codes: C08J 2433/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08J 2471/02 Polyalkylene oxides
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08L 5/00 Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

Contact lenses with hydrophilic polymer coatings are described herein along with methods of making such lenses. The contact lenses can include a lens core that comprises about 75% to about 100% silicone. The hydrophilic polymer coating can include polyethylene glycol and polyacrylamide.

Claims

1. A contact lens comprising:

a. a contact lens core comprising about 75% to about 100% silicone and;

b. a coating layer covalently attached to at least a portion of an outer surface of the contact lens core, the coating layer adapted to contact an ophthalmic surface, wherein the coating layer comprises a cross-linked, hydrophilic polymer, wherein the contact lens has an oxygen permeability Dk greater than 200*10̂

-11 (cm/sec)(ml 02/m1 x mm Hg).

2. The lens of claim 1, wherein the contact lens core comprises about 98% to about 100% silicone.

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

4. The lens of claim 1, wherein the contact lens has an oxygen permeability Dk greater than 250*10̂

-11 (cm/sec)(ml O2/ml×

mm Hg).

5. The lens of claim 1, wherein the contact lens has an oxygen permeability Dk greater than 300*10̂

-11 (cm/sec)(ml O2/ml×

mm Hg).

6. The lens of claim 1, wherein a surface of the contact lens has an advancing contact angle<

65 degrees.

7. The lens of claim 1, wherein a surface of the contact lens has an advancing contact angle<

60 degrees.

8. The lens of claim 1, wherein a surface of the contact lens has an advancing contact angle between<

55 degrees.

9. The lens of claim 1, wherein a surface of the contact lens has an advancing contact angle<

50 degrees.

10. The lens of claim 1, wherein a surface of the contact lens has an advancing contact angle<

45 degrees.

11. The lens of claim 1, wherein the contact lens surface has an advancing contact angle<

40 degrees.

12. The lens of claim 1, wherein the contact lens surface has an advancing contact angle<

35 degrees.

13. The lens of claim 1, wherein the contact lens surface has an advancing contact angle<

30 degrees.

14. The lens of claim 1, wherein the coating layer and core are covalently attached at the outer surface by an amine moiety.

15. The lens of claim 1, wherein the coating layer and core are covalently attached at the outer surface by an epoxide moiety.

16. The lens of claim 1, wherein the hydrophilic polymer comprises a first polymer species with a reactive sulfonyl group and a second polymer species with a reactive thiol, and the first polymer species and second polymer species are cross-linked by a thioether linkage.

17. The lens of claim 1, wherein the hydrophilic polymer comprises a first polymer species with a reactive sulfonyl group and a second polymer species with a reactive amine, and the first polymer species and second polymer species are cross-linked by a aminoether linkage.

18. The lens of claim 1, wherein the coating layer substantially surrounds an outer surface of the core.

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

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

21. The lens of claim 1, wherein the coating layer comprises a thickness between about 5 nm to about 30 nm.

22. The lens of claim 1, wherein the coating layer comprises a thickness between about 10 nm to about 50 nm.

23. The lens of claim 1, wherein the coating layer has a maximum thickness of less than about 10 microns.

24. The lens of claim 1, wherein a first portion of the coating layer comprises a first thickness different from a second thickness of a second portion of the coating layer.

25. The lens of claim 1, wherein the hydrophilic polymer comprises a branched species having a branch count between two to twelve branch arms.

26. The lens of claim 1, wherein the hydrophilic polymer includes a polymer species with a reactive electron pair accepting group and a polysaccharide species with a reactive nucleophilic group, the reactive electron pair accepting group and the reactive nucleophilic group adapted to react to thereby form cross-links between the polymer species to the polysaccharide species.

27. The lens of claim 26, wherein the reactive electron pair accepting group is a sulfonyl moiety.

28. The lens of claim 26, wherein the reactive nucleophilic group is an amine moiety.

29. The lens of claim 26, wherein the reactive electron pair accepting group of the polysaccharide species is covalently linked to the outer surface of the core.

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

31. The lens of claim 1, wherein the hydrophilic polymer comprises polyethylene glycol.

32. The lens of claim 1, wherein the hydrophilic polymer comprises polyacrylamide.

33. The lens of claim 1, wherein the hydrophilic polymer comprises a polysaccharide.

34. The lens of claim 33, wherein the polysaccharide comprises Chondroitin.

35. The lens of claim 33, wherein the polysaccharide comprises Chondroitin sulfate.

36. The lens of claim 33, wherein the polysaccharide comprises Dextran.

37. The lens of claim 33, wherein the polysaccharide comprises Dextran sulfate.

38. The lens of claim 33, wherein the polysaccharide comprises Hydroxyl propyl methyl cellulose.

39. A method of coating a contact lens core comprising:

a. Reacting an outer surface of the contact lens core with a first polymer species of a hydrophilic polymer solution, wherein the lens core is about 75% to about 100% silicone, 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

b. 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 and second polymer species, wherein a polymer hydrogel coating is formed and covalently attached to the outer surface of the contact lens core by the first and second nucleophilic conjugate reactions.

40. The method of claim 39, further comprising modifying an outer surface of the lens core to form a plurality of chemically reactive nucleophilic sites on the outer surface.

41. The method of claim 39, further comprising modifying an outer surface of the lens core to form a plurality of moieties that physically attract the polymer species to the lens surface.

42. The method of claim 39, further comprising modifying an outer surface of the lens core to form a combination of a plurality of chemically reactive sites as well as a plurality of physically attractive sites on the outer surface.

43. The method of claim 39, further comprising exposing the outer surface of the contact lens to a gas plasma treatment.

44. The method of claim 40, wherein the reactive nucleophilic sites on the outer surface include amines.

45. The method of claim 41, wherein the moieties on the outer surface include carboxylic acids.

46. The method of claim 39, further comprising modifying an outer surface of the lens core, wherein modifying includes the addition of an activator to a chemical mix used to form the lens core.

47. The method of claim 46, wherein the activator participates in a radical polymerization process of the chemical mix during fabrication of the lens core.

48. The method of claim 46, wherein the activator is a bifunctional polyethylene glycol.

49. The method of claim 48, wherein at least one moiety of the bifunctional activator does not participate in the radical polymerization process of the core lens during fabrication.

50. The method of claim 46, wherein the activator covalently bonds to a silane backbone of the lens core.

51. The method of claim 46, wherein the activator is N-(3-Aminopropyl)methacrylamide hydrochloride.

52. The method of claim 39, 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 a first portion of the electron pair accepting moiety on the first polymer species.

53. The method of claim 39, wherein the nucleophilic conjugate reactions are 1,4-nucleophilic addition reactions.

54. The method of claim 39, wherein the nucleophilic conjugate reactions are Michael-type reactions.

55. The method of claim 39, wherein the nucleophilic conjugate reactions are click reactions.

56. The method of claim 39, 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 sulfonyl group.

57. The method of claim 39, wherein the first polymer species and the second polymer species are cross-linked through an aminoether moiety.

58. The method of claim 39, wherein the nucleophilic reactive moiety of the second polymer species is an amine group and the electron pair accepting moiety of the first polymer species is a sulfonyl group.

59. The method of claim 39, wherein the first polymer species and the second polymer species are cross-linked through an aminoether moiety.

60. The method of claim 39, wherein the nucleophilic reactive moiety of the second polymer species is an amine group and the electron pair accepting moiety of the polysaccharide species is a sulfonyl group.

61. The method of claim 39, wherein the first polymer species and the polysaccharide species are cross-linked through an aminoether moiety.

62. The method of claim 39, wherein the hydrophilic polymer solution comprises substantially equivalent concentrations of the reactive moieties of the first polymer species and second polymer species.

63. The method of claim 39, wherein the concentrations of the reactive moieties of the first polymer species exceeds the concentration of the nucleophilic reactive moiety of the second polymer species by about 1% to about 50%.

64. The method of claim 39, wherein the reacting steps are performed at a temperature between about 15 degrees Celsius and about 60 degrees Celsius.

65. The method of claim 39, wherein the reacting steps are performed at a temperature of 120 degrees Celsius and 17 barr pressure

66. The method of claim 39, wherein the reacting steps are performed at a pH between about 7 and about 12.

67. The method of claim 39, wherein the polymer hydrogel coating is substantially optically clear.

68. The method of claim 39, wherein the contact lens comprises a core consisting of silicone.