Dimensionally stable silicone hydrogel contact lenses

• US 8,445,614 B2
• Filed: 02/24/2012
• Issued: 05/21/2013
• 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: Francis, Charles A., Xu, Yuan, Yao, Li, Back, Arthur, Hong, Ye, Chen, Charlie, Zheng, Ying
• Primary Examiner(s): Loewe, Robert S
• Application Number:
  US13/404,034
• Publication Number:
  US 20120220743A1
• Time in Patent Office: 452 Days
• Field of Search: None
• US Class Current: 526/279
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/103 of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
• CPC Class Codes: C08F 230/08 containing silicon

Abstract

Dimensionally stable silicone hydrogel contact lenses 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 represented by formula (2):

• • wherein R₁ of formula (2) is selected from either hydrogen atom or a methyl group; R₂ of formula (2) is selected from either of hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; m of formula (2) represents an integer of from 0 to 10; n of formula (2) represents an integer of from 4 to 100; a and b represent integers of 1 or more; a+b is equal to 20-500; b/(a+b) is equal to 0.01-0.22; the configuration of siloxane units includes a random configuration, the second siloxane monomer having a number average molecular weight of at least 3,000 daltons that is present in the polymerizable composition in an amount such that ratio of the first siloxane monomer to the second siloxane monomer is at least 2:1 based on unit parts by weight. 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 which 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.

3. The contact lens of claim 1, wherein in the first siloxane monomer, m of formula (1) is 4, n 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 first siloxane monomer has a number average molecular weight of from 400 daltons to 700 daltons.

5. The contact lens of claim 1, wherein the second siloxane monomer has a number average molecular weight greater than 7,000 daltons.

6. 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 is one integer from 65 to 90, b is one integer from 1 to 10, and R₁ of formula (2) is a methyl group.

7. The contact lens of claim 1, wherein the polymerizable composition comprises the at least one hydrophilic monomer, and the at least one hydrophilic monomer comprises at least one hydrophilic vinyl-containing monomer.

8. The contact lens of claim 7, wherein the at least one vinyl-containing monomer comprises at least one hydrophilic amide-containing monomer having one N-vinyl group.

9. The contact lens of claim 1, wherein the polymerizable composition comprises the at least one hydrophilic monomer, and the at least one hydrophilic monomer is present in the polymerizable composition in an amount from 30 unit parts to 60 unit parts.

10. The contact lens of claim 1, wherein the polymerizable composition comprises the at least one cross-linking agent, and the at least one cross-linking agent comprises at least one vinyl-containing cross-linking agent.

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 have an average dimensional stability variance of less than plus or minus three percent (±

3.0%), where the average dimensional stability variance is the variance in a value of a physical dimension when measured at an initial time point within one day of a manufacturing date of the batch of lenses, and at a second time point, where the second time point is from two weeks to seven years after the initial time point when the batch is stored at room temperature, or, when the batch is stored at a higher temperature, the second time point is a time point representative of storage of the batch from two weeks to seven years at room temperature, said average dimensional stability variance being an average of the dimensional stability variance determined for at least 20 individual lenses of the batch by the following equation (A);

(Diameter_Final−

Diameter_Original/Diameter_Original)×

100 

 

(A).

12. The batch of silicone hydrogel contact lenses recited in claim 11, wherein the average dimensional stability variance is less than plus or minus two percent (±

2.0%).

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

providing a polymerizable composition, said polymerizable composition comprising

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

14. The method of claim 13, further comprising repeating the steps to produce a plurality of the silicone hydrogel contact lenses having an average dimensional stability variance of less than plus or minus three percent (±

3.0%) over a time period from two weeks to seven years when stored at room temperature, or, when stored under accelerated shelf life testing conditions, for a time period and temperature equivalent to storage from two weeks to seven years at room temperature, said average dimensional stability variance being an average of the dimensional stability variance determined for at least 20 individual lenses of the batch by the following equation (A);

((Diameter_Final−

Diameter_Original)/Diameter_Original)×

100 

 

(A).

15. The method of claim 13, wherein in the first siloxane monomer, m of formula (1) is 4, n of formula (1) is 1, R¹ 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 13, wherein the first siloxane monomer has a number average molecular weight from about 400 daltons to about 700 daltons.

17. The method of claim 13, wherein the second siloxane monomer has a number average molecular weight greater than 7,000 daltons.

18. The method of claim 13, 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, and R₁ of formula (2) is a methyl group.

19. The method of claim 13, wherein the contacting step comprises contacting the polymeric lens body with a washing liquid comprising a volatile organic solvent.

20. The method of claim 13, wherein the contacting step comprises contacting the polymeric lens body with an aqueous washing liquid that is free of a volatile organic solvent.