Hybrid contact lenses prepared with expansion controlled polymeric materials

• US 7,828,432 B2
• Filed: 05/25/2007
• Issued: 11/09/2010
• Est. Priority Date: 05/25/2007
• Status: Active Grant

• Current Assignee: SynergEyes, Inc. (The Cooper Cos., Inc.)
• Original Assignee: SynergEyes, Inc. (The Cooper Cos., Inc.)
• Inventors: Collins, Joseph, Huynh, Jenny Xuan, Neidlinger, Hermann H., Dahi, Ali, Meyers, William E., Benrashid, Ramazan
• Primary Examiner(s): Sugarman; Scott J
• Application Number:
  US11/754,221
• Publication Number:
  US 20080291391A1
• Time in Patent Office: 1,264 Days
• Field of Search: 351/160.H, 351/160.R, 351/177
• US Class Current: 351/160.00H
• 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

A hybrid contact lens includes a substantially rigid center portion and a substantially flexible skirt portion connected to the center portion. The skirt portion is formed using xerogels compatible with diluents comprising at least one selected from polylactic acid, polyglycolic acid, lactide, glycolide, a polyacetal, a cyclic acetal, a polyketal, a cyclic ketal, a polyorthoester, a cyclic orthoester, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide. These diluents are formulated to function as a stand-in for water in the xerogel polymer, allowing the xerogel to form and bond to the rigid center portion in its fully expanded state. Upon hydration of the hybrid lens, substantially little dimensional change, and thus substantially little distortion, is obtained in the skirt portion. The diluents of the present invention further preserve the mechanical integrity of the xerogel, allowing the xerogel to be machined to final shape, improving the dimensional tolerances which can be achieved in the hybrid lens.

Claims

1. A hybrid contact lens blank, comprising:

a rigid center portion;

a skirt portion disposed about the center portion; and

a diluent dispersed within the skirt portion, wherein the diluent comprises at least one selected from polylactic acid, polyglycolic acid, lactide, glycolide, a polyacetal, a cyclic acetal, a polyketal, a cyclic ketal, a polyorthoester, a cyclic orthoester, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

2. The hybrid lens blank of claim 1, wherein the polyorthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

3. The hybrid lens blank of claim 1, wherein the cyclic orthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

4. The hybrid lens blank of claim 1, wherein the polyketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

5. The hybrid lens blank of claim 1, wherein the cyclic ketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

6. The hybrid lens blank of claim 1, wherein the diluent is configured to be readily removable by water during hydration of the lens blank.

7. The hybrid lens blank of claim 1, wherein the rigid center portion comprises a gas permeable material.

8. The hybrid lens blank of claim 1, wherein the skirt portion comprises a hydrogel polymer having a Dk greater than about 30 barrers.

9. The hybrid lens blank of claim 8, wherein the hydrogel comprises:

a vinyl amide recurring unit;

a polysiloxanylalkyl acrylate or methacrylate recurring unit;

a fluorine containing recurring unit;

a styrene containing recurring unit; and

a crosslinking unit.

10. The hybrid lens blank of claim 9, wherein the hydrogel comprises:

about 65 to about 75 mol % dimethylacrylamide recurring units;

about 25 to about 30 mol % tris(trimethylsiloxy)silylpropyl methacrylate recurring units;

about 0.2 to about 0.6 mol % 1,1,1,3,3,3-Hexafluoroisopropyl methacrylate recurring units;

about 1.5 to about 2 mol % styrene recurring units, and

about 1 to about 2 mol % ethyleneglycol dimethacrylate recurring units,

wherein the amount of each of the foregoing recurring units is on the basis of the total number of moles of recurring units in the hydrogel.

11. The hybrid lens blank of claim 1, wherein the skirt portion comprises a polymeric material that comprises one or more recurring units selected from linear (siloxanyl)alkyl (meth)acrylates, branched (siloxanyl)alkyl (meth)acrylates, cyclic (siloxanyl)alkyl (meth)acrylates, silicone-containing (meth)acrylates, fluorine-containing (meth)acrylates, hydroxyl group containing (meth)acrylates, (meth)acrylic acid, N-(meth)acryloylpyrrolidone, (meth)acrylamides, aminoalkyl (meth)acrylates, alkoxy group-containing (meth)acrylates, aromatic group containing (meth)acrylates, glycidyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, silicone-containing styrene derivatives, fluorine-containing styrene derivatives, styrene derivatives, and vinyl monomers.

12. The hybrid lens blank of claim 1, wherein the diluent is selected from the group consisting of L-lactide, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

13. The hybrid lens blank of claim 1, wherein the diluent is present in an amount sufficient to provide the skirt portion with an elastic modulus of at least about 3-14 kgf/cm2 after substantially full hydration.

14. The hybrid lens blank of claim 1, comprising about 5 to about 35 wt % of the diluent on the basis of the total weight of the skirt portion.

15. A xerogel polymer composition, comprising:

a vinyl amide recurring unit;

a polysiloxanylalkyl acrylate or methacrylate recurring unit;

a fluorine containing recurring unit;

a styrene containing recurring unit;

a crosslinking unit; and

a diluent comprising at least one selected from polylactic acid, polyglycolic acid, lactide, glycolide, a polyacetal, a cyclic acetal, a polyketal, a cyclic ketal, a polyorthoester, a cyclic orthoester, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

16. The xerogel polymer composition of claim 15, wherein the polyorthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

17. The xerogel polymer composition of claim 15, wherein the cyclic orthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

18. The xerogel polymer composition of claim 15, wherein the polyketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

19. The xerogel polymer composition of claim 15, wherein the cyclic ketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

20. The xerogel polymer composition of claim 15, wherein the diluent is selected from the group consisting of L-lactide, Di-t-butyl-dicarbonate, Tris(trimethylsilyl)amine, and 2,2,2-Trifluoroacetamide.

21. The xerogel polymer composition of claim 15, comprising about 5 to about 35 wt % of the diluent on the basis of the total weight of the polymer.

22. The xerogel polymer composition of claim 15, wherein the composition forms at least a portion of a contact lens.

23. A xerogel polymer composition, comprising:

a polymer; and

a diluent dispersed within the polymer, wherein the diluent comprises at least one selected from polylactic acid, polyglycolic acid, lactide, glycolide, a polyacetal, a cyclic acetal, a polyketal, a cyclic ketal, a polyorthoester, a cyclic orthoester, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide,

wherein the amount of diluent is selected so that upon substantially full hydration, the xerogel composition undergoes a linear expansion of less than approximately 8%.

24. The xerogel polymer composition of claim 23, wherein the polyorthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

25. The xerogel polymer composition of claim 23, wherein the cyclic orthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

26. The xerogel polymer composition of claim 23, wherein the polyketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

27. The xerogel polymer composition of claim 23, wherein the cyclic ketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

28. The xerogel polymer composition of claim 23, wherein the polymer comprises one or more recurring units selected from linear (siloxanyl)alkyl (meth)acrylates, branched (siloxanyl)alkyl (meth)acrylates, cyclic (siloxanyl)alkyl (meth)acrylates, silicone-containing (meth)acrylates, fluorine-containing (meth)acrylates, hydroxyl group containing (meth)acrylates, (meth)acrylic acid, N-(meth)acryloylpyrrolidone, (meth)acrylamides, aminoalkyl (meth)acrylates, alkoxy group-containing (meth)acrylates, aromatic group containing (meth)acrylates, glycidyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, silicone-containing styrene derivatives, fluorine-containing styrene derivatives, styrene derivatives, and vinyl monomers.

29. The xerogel polymer composition of claim 23, wherein the polymer comprises:

about 65 to about 75 mol % dimethylacrylamide recurring units;

about 25 to about 30 mol % tris(trimethylsiloxy)silylpropyl methacrylate recurring units;

about 0.2 to about 0.6 mol % 1,1,1,3,3,3-Hexafluoroisopropyl methacrylate recurring units;

about 1.5 to about 2 mol % styrene recurring units;

and about 1 to about 2 mol % ethyleneglycol dimethacrylate recurring units;

each of the foregoing recurring units being on the basis of the total number of moles of recurring units in the polymer.

30. The xerogel polymer composition of claim 23, wherein the diluent is selected from the group consisting of L-lactide, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

31. The xerogel polymer composition of claim 23, wherein the diluent is present in a concentration from about 5 to about 35 wt % on the basis of the total weight of the polymer.

32. The xerogel polymer composition of claim 23, wherein the composition forms at least a portion of a contact lens.

33. A hybrid contact lens, comprising:

a rigid center portion, comprising;

an acrylate recurring unit;

a styrene containing recurring unit;

a silicon containing recurring unit;

a fluorine containing recurring unit;

a cross-linking unit; and

an annular skirt portion coupled to the center portion at a junction between an outer peripheral edge of the center portion and an inner edge of the annular skirt portion, wherein the skirt portion comprises;

a vinyl amide recurring unit;

a polysiloxanylalkyl acrylate or methacrylate recurring unit;

a fluorine containing recurring unit;

a styrene containing recurring unit;

a cross-linking unit; and

a diluent dispersed within the skirt portion, wherein the diluent comprises at least one selected from polylactic acid, polyglycolic acid, lactide, glycolide, a polyacetal, a cyclic acetal, a polyketal, a cyclic ketal, a polyorthoester, a cyclic orthoester, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

34. The hybrid lens of claim 33, wherein the polyorthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

35. The hybrid lens of claim 33, wherein the cyclic orthoester comprises at least one selected from a methoxymethylene, an ethoxymethylene, a 1-(N,N-dimethylamino)ethylidene, a methanesulfonate and a toluenesulfonate.

36. The hybrid lens of claim 33, wherein the polyketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

37. The hybrid lens of claim 33, wherein the cyclic ketal comprises at least one selected from a methylene, a ethylidene and a 2,2,2-trichloroethylidene.

38. The hybrid lens of claim 33, wherein the rigid center portion comprises one or more polymeric materials comprising recurring units selected from linear alkyl (meth)acrylates, branched alkyl (meth)acrylates, cyclic (meth)acrylates, silicone-containing (meth)acrylates, fluorine-containing (meth)acrylates, hydroxyl group containing (meth)acrylates, (meth)acrylic acid, N-(meth)acryloylpyrrolidone, (meth)acrylamides, aminoalkyl (meth)acrylates, alkoxy group-containing (meth)acrylates, aromatic group containing (meth)acrylates, silicone-containing styrene derivatives, fluorine-containing styrene derivatives, styrene derivatives, and vinyl monomers.

39. The hybrid lens of claim 33, wherein the rigid center portion comprises:

about 1 to about 10 mol % methacrylic acid recurring units;

about 2 to about 11 mol % 2,6-dichlorostyrene recurring units;

about 10 to about 55 mol % styrylethyl-tris(trimethylsiloxy)silane recurring units;

about 1 to about 10 mol % [1,1,3,3-tetrakis[(trimethylsilyl)oxy]-1,3-disiloxanediyl]di-3,1-propanediyl dimethacrylate recurring units,

about 1 to about 8 mol % 1,1,1,3,3,3-Hexafluoroisopropyl methacrylate recurring units;

about 5 to about 35 mol % 3-[3,3,3-Trimethyl-1,1-bis [(trimethylsilyl)oxy]disiloxanyl]propyl methacrylate recurring units; and

about 1 to about 8 mol % of a crosslinking unit selected from the group consisting of divinyl benzene, ethyleneglycol dimethyacrylate, and vinyl methacrylate,

each of the foregoing recurring units on the basis of the total number of mols of recurring units of the rigid portion.

40. The hybrid lens of claim 33, wherein the diluent is substantially removed during hydration of the skirt portion.

41. The hybrid lens of claim 33, wherein the diluent is selected from the group consisting of L-lactide, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

42. The hybrid lens of claim 33, comprising about 5 to 35 wt % of the diluent on the basis of the total weight of the skirt portion.

43. A method for preparing a hybrid contact lens, the method comprising:

providing a substantially rigid center portion;

forming a peripheral skirt portion in the presence of the center portion, the skirt portion comprising a xerogel polymer and a diluent comprising at least one selected from polylactic acid, polyglycolic acid, lactide, glycolide, a polyacetal, a cyclic acetal, a polyketal, a cyclic ketal, a polyorthoester, a cyclic orthoester, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide; and

machining at least the skirt portion to a selected shape while the diluent is present in the skirt portion.

44. The method of claim 43, further comprising hydrating the hybrid contact lens to substantially replace the diluent with water.

45. The method of claim 43, wherein the diluent is selected from the group consisting of L-lactide, di-t-butyl-dicarbonate, tris(trimethylsilyl)amine, and 2,2,2-trifluoroacetamide.

46. The method of claim 43, wherein the diluent is present in an amount sufficient to provide the skirt portion with an elastic modulus of at least about 3-14 kgf/cm2 after substantially full hydration.

47. The method of claim 43, comprising about 5 to about 35 wt % of the diluent on the basis of the total weight of the skirt portion.

48. The method of claim 43, wherein the skirt portion is bonded to the center portion using one of conventional organic reactions at about the junction between the two portions or plasma treatment of the junction.