Silicone hydrogel contact lenses having acceptable levels of energy loss

• US 8,481,662 B2
• Filed: 02/24/2012
• Issued: 07/09/2013
• 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, Ronghua, Shi, Xinfeng, Liu, Yuwen, Chen, Charlie, Hong, Ye, Francis, Charles A., Yao, Li, Back, Arthur, Zheng, Ying
• Primary Examiner(s): Loewe, Robert S
• Application Number:
  US13/404,040
• Publication Number:
  US 20120220690A1
• Time in Patent Office: 501 Days
• Field of Search: None
• US Class Current: 526/279
• 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: 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

Silicone hydrogel contact lenses having ophthalmically acceptable levels of energy loss are described. The lenses are derived from a polymerizable composition including a first siloxane monomer represented by formula (1):

wherein m of formula (1) represents one integer from 3 to 10, n of formula (1) represents one integer from 1 to 10, R¹ of formula (1) is an alkyl group having from 1 to 4 carbon atoms, and each R² of formula (1) is independently either a hydrogen atom or a methyl group; the lenses also include units derived from a second siloxane monomer which is a dual-end methacrylate end-capped polydimethylsiloxane having a number average molecular weight of at least 7,000 daltons. 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 polymerizable composition, said polymerizable composition comprising

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

2. The contact lens of claim 1, wherein the silicone hydrogel contact lens, when fully hydrated, has an energy loss from about 27% to about 40%.

3. 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.

4. The contact lens of claim 1, wherein the number average molecular weight of the first siloxane monomer is from 400 daltons to 700 daltons.

5. The contact lens of claim 1, wherein the polymerizable composition further comprises at least one cross-linking agent.

6. The contact lens of claim 5, wherein the at least one cross-linking agent comprises a vinyl-containing cross-linking agent.

7. The contact lens of claim 6, wherein a total amount of vinyl-containing cross-linking agents present in the polymerizable composition is from about 0.01 unit parts to about 2.0 unit parts by weight.

8. The contact lens of claim 7, wherein a ratio of an amount of the first siloxane monomer present in the polymerizable composition to the total amount of vinyl-containing cross-linking agents present in the polymerizable composition is from 100:

1 to 400;

1 based on unit parts by weight.

9. The contact lens of claim 1, wherein the polymerizable composition further comprises at least one hydrophilic monomer.

10. The contact lens of claim 9, wherein the at least one hydrophilic monomer comprises a hydrophilic amide monomer having one N-vinyl group.

11. The contact lens of claim 1, wherein a ratio of an amount of the first siloxane monomer present in the polymerizable composition to an amount of the second siloxane monomer present in the polymerizable composition is at least 3:

1 based on unit parts by weight.

12. The contact lens of claim 1, wherein a total amount of siloxane monomers present in the polymerizable composition is from about 35 to about 40 unit parts by weight.

13. The contact lens of claim 1, wherein in the second siloxane monomer, m of formula (2) is 0, n of formula (2) is one integer from 5 to 10, a of formula (2) is one integer from 65 to 90, b of formula (2) is one integer from 1 to 10, and R₁ of formula (2) is a methyl group.

14. 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, when fully hydrated, an average equilibrium water content (EWC) from about 30% wt/wt to about 70% wt/wt, or an average oxygen permeability of at least 55 barrers, or an average captive bubble dynamic advancing contact angle less than 70 degrees, or an average captive bubble static contact angle less than 55 degrees, or any combination thereof, based on averages of values determined for at least 20 individual lenses of the batch.

15. 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);

16. The method of claim 15, wherein the contacting step comprises contacting the polymeric lens body with a washing liquid that is free of a volatile organic solvent.

17. The method of claim 15, wherein the number average molecular weight of the first siloxane monomer is from 400 daltons to 700 daltons.