Wettable Silicone Hydrogel Contact Lenses

• US 20120220744A1
• Filed: 02/24/2012
• Published: 08/30/2012
• 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: Liu, Yuwen, Chen, Charlie, Francis, Charles A., Xu, Yuan, Yao, Li, Back, Arthur, Ge, Junhao, Zheng, Ying
• Granted Patent: US 8,487,058 B2
• Time in Patent Office: Days
• US Class Current: 526/279
• CPC Class Codes: B65B 5/04 Packaging single articles
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 83/12 containing polyether sequences
• 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

Abstract

Ophthalmically acceptably wettable silicone hydrogel contact lenses are described. The lenses are derived from a polymerizable composition including a first siloxane monomer. The lenses have ophthalmically acceptably wettable lens surfaces when fully hydrated. Batches of silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses are also described.

Claims

1. A silicone hydrogel contact lens, comprising:

a polymeric lens body that is the reaction product of a miscible polymerizable composition, said polymerizable composition comprising

(a) a first siloxane monomer represented by formula (1);

2. The contact lens of claim 1, wherein the contact lens has the ophthalmically acceptably wettable surfaces when the polymerizable composition used to form the polymeric lens body is free of an internal wetting agent, or when the polymerizable composition used to form the polymeric lens body is free of an organic diluent, or when the lens is washed in a liquid free of a volatile organic solvent, or when the lens is free of a surface plasma treatment, or any combination thereof.

3. The contact lens of claim 1, wherein the contact lens has an equilibrium water content (EWC) from 30% to 70% when fully hydrated.

4. The contact lens of claim 1, wherein the polymeric lens has a captive bubble dynamic advancing contact angle less than 70 degrees when fully hydrated.

5. The contact lens of claim 1, wherein the polymerizable composition is essentially free of N,N-dimethylacrylamide (DMA)

6. The contact lens of claim 1, wherein the first siloxane monomer and the second siloxane monomer are present in the polymerizable composition in a ratio from about 2:

1 to about 10;

1 based on unit parts.

7. The contact lens of claim 1, wherein in the first siloxane monomer, m of formula (1) is 4, n of formula (1) is 1, R¹ of formula (1) is a butyl group, and each R² of formula (1) is independently either a hydrogen atom or a methyl group.

8. The contact lens of claim 1, wherein the polymerizable composition is essentially free of an organic diluent.

9. The contact lens of claim 1, wherein the second siloxane monomer is represented by formula (2):

10. The contact lens of claim 9, wherein in the second siloxane monomer, m of formula (2) is 0, n of formula (2) is one integer from 5 to 10, a is one integer from 65 to 90, b is one integer from 1 to 10, R₁ of formula (2) is a methyl group, and R₂ of formula (2) is either a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms.

11. A batch of silicone hydrogel contact lenses, comprising a plurality of the contact lens recited in claim 1, wherein the batch of silicone hydrogel contact lenses has an average equilibrium water content (EWC) from 30% to 70% when fully hydrated, or an average oxygen permeability of at least 55 barrers, or an average tensile modulus from about 0.2 MPa to about 0.9 MPa when fully hydrated, or an average captive bubble dynamic advancing contact angle less than 70 degrees when fully hydrated, or an average captive bubble static contact angle less than 55 degrees when fully hydrated, or any combination thereof, based on averages of values determined for at least 20 individual lenses of the batch.

12. A method of manufacturing a silicone hydrogel contact lens, comprising:

providing a miscible polymerizable composition, said polymerizable composition comprising

(a) a first siloxane monomer represented by formula (1);

13. The method of claim 12, wherein the contact lens has the ophthalmically acceptably wettable lens surfaces when the polymerizable composition used to form the polymeric lens body is free of an internal wetting agent, or when the polymerizable composition used to form the lens is free of an organic diluent, or when the lens is washed in a liquid free of a volatile organic solvent, or when the lens is free of a surface plasma treatment, or any combination thereof.

14. The method of claim 12, further comprising the step of autoclaving the contact lens package to sterilize the polymeric lens body and the contact lens packaging solution.

15. The method of claim 12, wherein in the first siloxane monomer, m of formula (1) is 4, n of formula (1) is 1, R¹ of formula (1) is a butyl group, and each R² of formula (1) is independently either a hydrogen atom or a methyl group.

16. The method of claim 12, wherein the polymerizable composition further comprises a second siloxane monomer is represented by formula (2):

17. The method of claim 16, wherein in the second siloxane monomer, m of formula (2) is 0, n of formula (2) is one integer from 5 to 10, a is one integer from 65 to 90, b is one integer from 1 to 10, R₁ of formula (2) is a methyl group, and R₂ of formula (2) is either a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms.

18. The method of claim 12, wherein the polymerizing step comprises polymerizing the polymerizable composition in a contact lens mold assembly having a molding surface formed of a non-polar thermoplastic polymer to form a polymeric lens body.

19. The method of claim 12, wherein the polymerizing step comprises polymerizing the polymerizable composition in a contact lens mold assembly having a molding surface formed of a polar thermoplastic polymer to form a polymeric lens body.

20. The method of claim 12, wherein the contacting step comprises contacting the polymeric lens body with a washing liquid comprising at least one volatile organic solvent.