CONTACT LENS WITH A HYDROPHILIC LAYER

• US 20160223836A1
• Filed: 04/11/2016
• Published: 08/04/2016
• Est. Priority Date: 11/15/2013
• Status: Active Grant

• Current Assignee: Tangible Science, Llc
• Original Assignee: Brandon Mcnary Felkins, Karen L. Havenstrite, Paul A. Cook, Victor Wayne Mccray
• Inventors: HAVENSTRITE, Karen L., MCCRAY, Victor Wayne, FELKINS, Brandon McNary, COOK, Paul A.
• Granted Patent: US 10,330,951 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: A61B 5/01 Measuring temperature of body parts ; Diagnostic temperature sensing, e.g. for malignant or inflamed tissue clinical contact thermometers G01K13/20
• CPC Class Codes: A61B 5/02 Detecting, measuring or recording pulse, heart rate, blood pressure or blood flow; Combined pulse/heart-rate/blood pressure determination; Evaluating a cardiovascular condition not otherwise provided for, e.g. using combinations of techniques provided for in this group with electrocardiography or electroauscultation; Heart catheters for measuring blood pressure
• CPC Class Codes: A61B 5/14507 specially adapted for measuring characteristics of body fluids other than blood devices for taking samples of body liquids A61B10/0045
• CPC Class Codes: A61B 5/14532 for measuring glucose, e.g. by tissue impedance measurement
• CPC Class Codes: B29D 11/00 Producing optical elements, e.g. lenses or prisms grinding or polishing of optical elements B24B; constructional form of optical elements G02B; optical parts of spectacles G02C7/00
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00788 Producing optical films
• 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 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08L 83/04 Polysiloxanes
• 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 7/04 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

Embodiments of the technology relate to a contact lens having a core that is coated by a hydrogel layer, and to methods of making such a lens. The coated lens can include a rigid gas permeable contact lens. The coated lens can also include a hybrid silicone and rigid gas permeable contact lens. In one aspect, embodiments provide for a coated contact lens comprising a lens core with a water equilibrium constant of less than about 2% 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 of one or more species.

Claims

1. A coated contact lens comprising:

a lens core with an equilibrium water content of less than about 2%, the 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 of one or more species.

2. The lens of claim 1, wherein the one or more species are at least partially cross-linked.

3. The lens of claim 1, wherein the lens core is substantially free of water.

4. The lens of claim 1, wherein the hydrophilic polymer population includes a first species selected from the group consisting of:

polyethylene glycol (PEG), phosphorylcholine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(N-isopropylacrylamide) (PNIPAM), polyacrylamide (PAM), poly(2-oxazoline), polyethylenimine (PEI), poly(acrylic acid), polymethacrylate, polyelectrolytes, hyaluronic acid, chitosan, chondroitin sulfate, alginate, hydroxypropylmethylcellulose, and dextran.

5. The lens of claim 1, wherein the hydrophilic polymer population includes a second species selected from the group consisting of:

polyethylene glycol (PEG), phosphorylcholine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(N-isopropylacrylamide) (PNIPAM), polyacrylamide (PAM), poly(2-oxazoline), polyethylenimine (PEI), poly(acrylic acid), polymethacrylate, polyelectrolytes, hyaluronic acid, chitosan, chondroitin sulfate, alginate, hydroxypropylmethylcellulose, and dextran.

6. The lens of claim 1, wherein the hydrophilic polymer population includes a first species comprising PEG.

7. The lens of claim 1, wherein the hydrophilic polymer population includes a second species comprising polyacrylamide.

8. The lens of claim 1, wherein the contact lens is a rigid gas permeable contact lens.

9. The lens of claim 1, wherein the lens core comprises a rigid gas permeable material.

10. The lens of claim 1, wherein the lens core consists essentially of a cross-linked polysiloxane.

11. The lens of claim 1, wherein the lens core is a soft contact lens.

12. The lens of claim 1, wherein the hydrogel layer has a thickness less than about 5 micron.

13. The lens of claim 1, wherein the hydrogel layer comprises a thickness less than about 50 nm.

14. The lens of claim 1, wherein the first species comprises a reactive electrophilic group or a reactive nucleophilic group and the second species comprises a reactive electrophilic group or a reactive nucleophilic group complementary to the first species, the reactive electrophilic group and the reactive nucleophilic group adapted to react to thereby form cross-links between the first species to the second species.

15. The lens of claim 14, wherein the reactive electrophilic group is selected from the group consisting of:

amino-reactive groups, sulfhydryl-reactive groups, carboxyl groups, hydroxyl groups, haloalkyl groups, dienophile groups, aldehyde or ketone groups, alkenes, epoxides, and phosphoramidites.

16. The lens of claim 14, wherein the reactive nucleophilic group is selected from the group consisting of:

amines, amino-reactive groups, sulfhydryl, sulfhydryl-reactive groups, carboxyl groups, hydroxyl groups, haloalkyl groups, dienophile groups, aldehyde or ketone groups, alkenes, epoxides, and phosphoramidites.

17. The lens of claim 14, wherein at least one of the reactive electrophilic group of the first species or the reactive electrophilic group of the second species is covalently linked to the outer surface of the core.

18. The lens of claim 1, wherein the lens has an advancing contact angle as measured by a captive bubble test of less than about 35 degrees.

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

20. The lens of claim 1, wherein the lens has a critical coefficient of friction of less than about 0.05.

21. The lens of claim 1, wherein the lens has a water break up time of greater than about 20 seconds.

22. The lens of claim 1, wherein the lens does not substantially denature proteins.

23. The lens of claim 1, wherein the hydrophilic polymer layer further comprises at least one active agent.

24. The lens of claim 23, 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.

25. The lens of claim 1, wherein the lens has an oxygen transmissibility (DK/t) of greater than 200.

26. A contact lens comprising:

a coated soft lens with an oxygen transmissibility (Dk/t) of greater than about 200, the coated soft lens comprising a lens core with an outer surface and a coating, the coated lens adapted for on-eye movement that is adequate to maintain the health of the ophthalmic surface and wearer comfort.

27. The lens of claim 26, wherein the soft lens includes a hydrogel layer coating.

28. The lens of claim 26, wherein the hydrogel layer is covalently attached to an outer surface of the lens core.

29. The lens of claim 26, wherein the lens core comprises a cross-linked polysiloxane.

30. The lens of claim 26, wherein the core comprises a sensor.

31. The lens of claim 26, wherein the core comprises a glucose sensor.

32. The lens of claim 26, wherein the core comprises a biometric sensor.

33. The lens of claim 26, wherein the core comprises one or more of a conductive metal material, a camera, a power source, electronics, wireless transmitter, and memory.

34. 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 a moiety at a first portion that forms a covalent attachment to the outer surface of the contact lens; 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 moiety that forms a covalent bond to a second portion of the first polymer species in a second covalent reaction thereby forming a hydrogel coating comprising the first polymer species and the second polymer species at least partially cross-linked.

35. The method of claim 34, wherein the covalent attachment between the outer surface of the contact lens and the first portion of the first polymer species is formed by a first nucleophilic conjugate reaction.

36. The method of claim 34, wherein the second covalent reaction is a second nucleophilic conjugate reaction.

37. The method of claim 34, wherein the partial cross-linking is between an electrophilic moiety of the first species and a nucleophilic moiety of the second species in a nucleophilic conjugate reaction.

38. The method of claim 34, wherein the hydrophilic polymer population includes a first species selected from the group consisting of:

polyethylene glycol (PEG), phosphorylcholine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(N-isopropylacrylamide) (PNIPAM), polyacrylamide (PAM), poly(2-oxazoline), polyethylenimine (PEI), poly(acrylic acid), polymethacrylate, polyelectrolytes, hyaluronic acid, chitosan, chondroitin sulfate, alginate, hydroxypropylmethylcellulose, and dextran.

39. The method of claim 34, wherein the hydrophilic polymer population includes a second species selected from the group consisting of:

polyethylene glycol (PEG), phosphorylcholine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(N-isopropylacrylamide) (PNIPAM), polyacrylamide (PAM), poly(2-oxazoline), polyethylenimine (PEI), poly(acrylic acid), polymethacrylate, polyelectrolytes, hyaluronic acid, chitosan, chondroitin sulfate, alginate, hydroxypropylmethylcellulose, and dextran.

40. The method of claim 34, wherein the first species comprises a reactive electrophilic group or a reactive nucleophilic group and the second species comprises a reactive electrophilic group or a reactive nucleophilic group complementary to the first species, the reactive electrophilic group and the reactive nucleophilic group adapted to react to thereby form cross-links between the first species to the second species.

41. The method of claim 40, wherein the reactive electrophilic group is selected from the group consisting of:

amino-reactive groups, sulfhydryl-reactive groups, carboxyl groups, hydroxyl groups, haloalkyl groups, dienophile groups, aldehyde or ketone groups, alkenes, epoxides, and phosphoramidites.

42. The method of claim 40, wherein the reactive nucleophilic group is selected from the group consisting of:

amines, amino-reactive groups, sulfhydryl, sulfhydryl-reactive groups, carboxyl groups, hydroxyl groups, haloalkyl groups, dienophile groups, aldehyde or ketone groups, alkenes, epoxides, and phosphoramidites.

43. The method of claim 40, wherein at least one of the reactive electrophilic group of the first species or the reactive electrophilic group of the second species is covalently linked to the outer surface of the contact lens.

44. The method of claim 34, wherein the contact lens comprises a rigid gas permeable lens.

45. The method of claim 44, further comprising modifying an outer surface of a contact lens to form the plurality of reactive nucleophilic sites or a plurality of electrophilic sites on the outer surface.

46. The method of claim 34, wherein the modifying step comprises exposing the outer surface of the contact lens to a gas plasma treatment.

47. The method of claim 34, further comprising adding a bifunctional monomer or a polymer to a prepolymerization mixture used to form the contact lens.

48. The method of claim 47, wherein the bifunctional monomer or polymer provides additional nucleophilic or electrophilic reactive sites on the surface of the contact lens.

49. The method of claim 48, wherein modifying the outer surface of the contact lens includes one or more of:

pH adjustment, plasma activation, light activation, activation of the liquid monomer mix, wet activation, and adding a monomer that reacts with the contact lens that still leaves reactive sites.

50. The method of claim 34, wherein the contact lens comprises a core comprising polysiloxane.

51. The method of claim 34, wherein the contact lens comprises a core substantially free of polysiloxane.

52. The method of claim 34, wherein the contact lens comprises a hydrogel core.

53. The method of claim 34, wherein the hydrogel coated contact lens has an oxygen transmissibility (DK/t) of greater than 200.

54. The method of claim 34, wherein the hydrogel layer comprises a thickness between about 1 nm to about 50 nm.