Silicone hydrogel contact lenses

• US 8,820,928 B2
• Filed: 02/24/2012
• Issued: 09/02/2014
• Est. Priority Date: 02/28/2011
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Back, Arthur, Morsley, David Robert, Rogers, Richard, Almond, Sarah, Chen, Charlie, Liu, Yuwen, Francis, Charles A., Hong, Ye
• Primary Examiner(s): SCHWARTZ, JORDAN MARC
• Application Number:
  US13/404,033
• Publication Number:
  US 20120218509A1
• Time in Patent Office: 921 Days
• Field of Search: 351/159.33, 351/159.73, 351/159.78
• US Class Current: 351/159.73
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Silicone hydrogel contact lenses are produced without using volatile organic solvents to extract materials from the polymerized contact lens bodies, and instead are washed with aqueous liquids. The silicone hydrogel contact lenses so produced have ophthalmically wettable lens surfaces such that less than five percent of a batch of twenty or more such silicone hydrogel contact lenses have visually identifiable non-wetting spots when the contact lenses are located on eyes of subjects.

Claims

1. A method of manufacturing a batch of silicone hydrogel contact lenses, comprising:

providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of the silicone hydrogel contact lens body, and the first mold section and second mold section are coupled together;

separating the polymerized silicone hydrogel contact lens bodies from the contact lens mold assemblies to produce delensed contact lens bodies;

washing the delensed contact lens bodies with an aqueous liquid free of volatile organic solvent to produce washed contact lenses; and

sterilizing the washed contact lenses in sealed contact lens packages;

wherein the batch so manufactured comprises at least twenty silicone hydrogel contact lenses, and the anterior surfaces of the sterilized contact lenses have clinically acceptable surface wettabilities such that less than five percent of the silicone hydrogel contact lenses have visually identifiable non-wetting spots when located on eyes of subjects, and wherein the non-wetting spots are discontinuities of the contact lens wearer'"'"'s pre-lens tear film present on the anterior surface of the contact lens, and are visually identifiable during a slit lamp examination at a total magnification from about 6×

to about 70×

;

wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a siloxane monomer represented by formula (1);

2. The method of claim 1, wherein at least one of the first mold section or the second mold section comprises a polar resin having a polarity from 1% to 7%.

3. The method of claim 1, wherein at least one of the first mold section or the second mold section comprises a polybutylene terephthalate (PBT) resin.

4. The method of claim 1, wherein each polymerized contact lens body is obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation, or ultraviolet radiation, or both.

5. The method of claim 1, wherein each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one cross-linking agent, and said polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both.

6. The method of claim 5, wherein the polymerizable composition comprises at least one hydrophilic vinyl monomer and at least one vinyl cross-linking agent.

7. The method of claim 1, wherein the batch of sterilized silicone hydrogel contact lenses has an average diameter that is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step.

8. The method of claim 1, wherein each of the sterilized silicone hydrogel contact lenses has an oxygen permeability of at least 55 barrers, or an equilibrium water content from about 30% wt/wt to about 70% wt/wt, or a tensile modulus from about 0.2 MPa to about 0.9 MPa, or any combination thereof.

11. The method of claim 1, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a hydrophilic amide monomer having one N-vinyl group, and the polymerized silicone hydrogel contact lens bodies comprise a copolymer including polymerized units of the hydrophilic amide monomer having one N-vinyl group.

12. The method of claim 1, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a vinyl-containing cross-linking agent, and the polymerized silicone hydrogel contact lens bodies comprise a copolymer including polymerized units of the vinyl-containing cross-linking agent.

9. A method of manufacturing a batch of silicone hydrogel contact lenses, comprising:

providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of the silicone hydrogel contact lens body, and the first mold section and second mold section are coupled together;

separating the polymerized silicone hydrogel contact lens bodies from the contact lens mold assemblies to produce delensed contact lens bodies;

washing the delensed contact lens bodies with an aqueous liquid free of volatile organic solvent to produce washed contact lenses; and

sterilizing the washed contact lenses in sealed contact lens packages;

wherein the batch so manufactured comprises at least twenty silicone hydrogel contact lenses, and the anterior surfaces of the sterilized contact lenses have clinically acceptable surface wettabilities such that less than five percent of the silicone hydrogel contact lenses have visually identifiable non-wetting spots when located on eyes of subjects, and wherein the non-wetting spots are discontinuities of the contact lens wearer'"'"'s pre-lens tear film present on the anterior surface of the contact lens, and are visually identifiable during a slit lamp examination at a total magnification from about 6×

to about 70×

,

wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a siloxane monomer represented by formula (2);

20. The method of claim 9, wherein at least one of the first mold section or the second mold section comprises a polar resin having a polarity from 1% to 7%.

21. The method of claim 9, wherein at least one of the first mold section or the second mold section comprises a polybutylene terephthalate (PBT) resin.

22. The method of claim 9, wherein each polymerized contact lens body is obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation, or ultraviolet radiation, or both.

23. The method of claim 9, wherein each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one cross-linking agent, and said polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both.

24. The method of claim 23, wherein the polymerizable composition comprises at least one hydrophilic vinyl monomer and at least one vinyl cross-linking agent.

25. The method of claim 9, wherein the batch of sterilized silicone hydrogel contact lenses has an average diameter that is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step.

26. The method of claim 9, wherein each of the sterilized silicone hydrogel contact lenses has an oxygen permeability of at least 55 barrers, or an equilibrium water content from about 30% wt/wt to about 70% wt/wt, or a tensile modulus from about 0.2 MPa to about 0.9 MPa, or any combination thereof.

27. The method of claim 9, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a hydrophilic amide monomer having one N-vinyl group, and the polymerized silicone hydrogel contact lens bodies comprise a copolymer including polymerized units of the hydrophilic amide monomer having one N-vinyl group.

28. The method of claim 9, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a vinyl-containing cross-linking agent, and the polymerized silicone hydrogel contact lens bodies comprise a copolymer including polymerized units of the vinyl-containing cross-linking agent.

10. A method of manufacturing a batch of silicone hydrogel contact lenses, comprising:

providing polymerized silicone hydrogel contact lens bodies in contact lens mold assemblies, wherein a single polymerized silicone hydrogel contact lens body is provided in a single contact lens mold assembly, and each contact lens mold assembly comprises a first mold section having a concave optical surface for forming an anterior surface of the silicone hydrogel contact lens body and a second mold section having a convex optical surface for forming a posterior surface of the silicone hydrogel contact lens body, and the first mold section and second mold section are coupled together;

separating the polymerized silicone hydrogel contact lens bodies from the contact lens mold assemblies to produce delensed contact lens bodies;

washing the delensed contact lens bodies with an aqueous liquid free of volatile organic solvent to produce washed contact lenses; and

sterilizing the washed contact lenses in sealed contact lens packages;

wherein the batch so manufactured comprises at least twenty silicone hydrogel contact lenses, and the anterior surfaces of the sterilized contact lenses have clinically acceptable surface wettabilities such that less than five percent of the silicone hydrogel contact lenses have visually identifiable non-wetting spots when located on eyes of subjects, and wherein the non-wetting spots are discontinuities of the contact lens wearer'"'"'s pre-lens tear film present on the anterior surface of the contact lens, and are visually identifiable during a slit lamp examination at a total magnification from about 6×

to about 70×

,

wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a siloxane monomer represented by formula (6);

29. The method of claim 10, wherein at least one of the first mold section or the second mold section comprises a polar resin having a polarity from 1% to 7%.

30. The method of claim 10, wherein at least one of the first mold section or the second mold section comprises a polybutylene terephthalate (PBT) resin.

31. The method of claim 10, wherein each polymerized contact lens body is obtained by polymerizing a polymerizable composition in a contact lens mold assembly using thermal radiation, or ultraviolet radiation, or both.

32. The method of claim 10, wherein each polymerized silicone hydrogel contact lens body is obtained by polymerizing a polymerizable composition comprising a first siloxane monomer, a second siloxane monomer, at least one hydrophilic monomer, at least one hydrophobic monomer, and at least one cross-linking agent, and said polymerizable composition is free of a diluent, or free of a hydrophilic polymer, or both.

33. The method of claim 32, wherein the polymerizable composition comprises at least one hydrophilic vinyl monomer and at least one vinyl cross-linking agent.

34. The method of claim 10, wherein the batch of sterilized silicone hydrogel contact lenses has an average diameter that is at least 20% greater than the average diameter of the same batch of silicone hydrogel contact lens bodies prior to the washing step.

35. The method of claim 10, wherein each of the sterilized silicone hydrogel contact lenses has an oxygen permeability of at least 55 barrers, or an equilibrium water content from about 30% wt/wt to about 70% wt/wt, or a tensile modulus from about 0.2 MPa to about 0.9 MPa, or any combination thereof.

36. The method of claim 10, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a hydrophilic amide monomer having one N-vinyl group, and the polymerized silicone hydrogel contact lens bodies comprise a copolymer including polymerized units of the hydrophilic amide monomer having one N-vinyl group.

37. The method of claim 10, wherein a polymerizable composition used to form the polymerized silicone hydrogel contact lens bodies comprises a vinyl-containing cross-linking agent, and the polymerized silicone hydrogel contact lens bodies comprise a copolymer including polymerized units of the vinyl-containing cross-linking agent.

13. A batch of silicone hydrogel contact lenses, the batch comprising:

at least twenty silicone hydrogel contact lenses, each silicone hydrogel contact lens of the batch is an aqueous extracted silicone hydrogel contact lens comprising an anterior surface and an opposing posterior surface, the posterior surface dimensioned by size and shape for placement against a subject'"'"'s eye;

the anterior surface of each of the aqueous extracted contact lenses having a clinically acceptable surface wettability, such that less than five percent of the batch of silicone hydrogel contact lenses has visually identifiable non-wetting spots when located on eyes of subject;

wherein the non-wetting spots are discontinuities of the contact lens wearer'"'"'s pre-lens tear film present on the anterior surface of the contact lenses, and are visually identifiable during a slit lamp examination at a total magnification from about 6×

to about 70×

, and

wherein a) a polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (1);

14. The batch of silicone hydrogel contact lenses of claim 13, wherein each silicone hydrogel contact lens is a cast molded silicone hydrogel contact lens without a plasma surface treatment or a polymeric internal wetting agent provided by including a hydrophilic polymer in the polymerizable composition used to form the silicone hydrogel contact lens.

15. The batch of silicone hydrogel contact lenses of claim 13, wherein each silicone hydrogel contact lens is a cast molded silicone hydrogel contact lens obtained from a contact lens mold assembly, the contact lens mold assembly comprising an anterior mold member and a posterior mold member, each mold member being formed from a polar resin having a polarity from about 1% to about 7%.

16. The batch of silicone hydrogel contact lenses of claim 15, wherein the polar resin is polybutylene terephthalate (PBT).

17. The batch of silicone hydrogel contact lenses of claim 13, wherein each contact lens comprises a polymeric component and a liquid component, the polymeric component comprising units of at least one siloxane having one or more functional acrylic groups, and units of one or more hydrophilic monomers having one or more functional non-acrylic vinyl groups.

18. The batch of silicone hydrogel contact lenses of claim 13, wherein each contact lens has an oxygen permeability of at least 55 barrers, or an equilibrium water content from about 30% wt/wt to about 70% wt/wt, or a tensile modulus from about 0.2 MPa to about 0.9 MPa, or any combination thereof.

19. The batch of silicone hydrogel contact lenses of claim 13, wherein each silicone hydrogel is provided in a sterilized contact lens packaging solution, and each lens body has a wet extractable content less than 10% (wt/wt).

38. The batch of claim 13, wherein the polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (1):

39. The batch of claim 13, wherein the polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (2):

40. The batch of claim 13, wherein the polymerizable composition used to form the silicone hydrogel contact lenses comprises a siloxane monomer represented by formula (6):