Phosphine-containing hydrogel contact lenses

• US 9,864,103 B2
• Filed: 01/20/2014
• Issued: 01/09/2018
• 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: Wang, Guigui, Zhang, Yun, Liu, Yuwen, Hong, Ye, Chen, Charlie, Zhu, Peter
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/158,879
• Publication Number:
  US 20140131227A1
• Time in Patent Office: 1,450 Days
• Field of Search: None
• CPC Class Codes: A45C 11/005 Contact lens cases A45C11/046 takes precedence
• CPC Class Codes: B65D 81/22 in moist conditions or immersed in liquids
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Hydrogel contact lenses that are derived from a polymerizable composition including at least one hydrophilic monomer and at least one phosphine-containing component are described. The hydrogel of the contact lenses can be a silicone hydrogel or a non-silicone hydrogel. Use of polymerizable compositions comprising a phosphine-containing component can be cured under both inert and air atmospheres, and can be used to form hydrogel contact lenses having improved shape retention properties, having improved resistance to discoloration. Batches of hydrogel contact lenses and methods of making hydrogel contact lenses are also described.

Claims

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

providing a polymerizable composition comprising

(a) at least one hydrophilic monomer, and

(b) at least one phosphine-containing compound, wherein the at least one phosphine-containing compound is present in an unoxidized form at the time it is combined with the at least one hydrophilic monomer in the polymerizable composition, and

(c) at least one thermal initiator, wherein (b) and (c) are different from each other; and

(d) thermally curing the polymerizable composition to form a polymeric lens body.

2. The method of claim 1, wherein the phosphine-containing compound has a structure represented by formula (1):

3. The method of claim 1, wherein the phosphine-containing compound is a polymerizable phosphine-containing compound.

4. The method of any claim 1, wherein the phosphine-containing compound comprises triphenylphosphine, or diphenyl(4-vinylphenyl)phosphine, or both.

5. The method of claim 1, wherein the phosphine compound is present in the polymerizable composition in an amount from 0.01 to 5 unit parts.

6. The method of claim 1, wherein the polymerizable composition contains an amount of the phosphine-containing compound effective to scavenge at least a portion of oxygen present in the polymerizable composition during the manufacturing.

7. The method of claim 1, wherein the polymerizable composition contains an amount of the phosphine-containing compound effective to produce a polymeric lens body having a reduced amount of axial edge lift (AEL) as compared to a second hydrogel contact lens body formed from a second polymerizable composition substantially identical to the polymerizable composition except without the phosphine-containing compound and using a manufacturing process substantially identical to the manufacturing process of the hydrogel contact lens.

8. The method of claim 1, wherein the polymerizable composition contains an amount of the phosphine-containing compound effective to reduce distortion of the hydrogel contact lens as compared to a second hydrogel contact lens body formed from a second polymerizable composition substantially identical to the polymerizable composition except without the phosphine-containing compound and using a manufacturing process substantially identical to the manufacturing process of the hydrogel contact lens.

9. The method of claim 1, wherein the thermally curing of the polymerizable composition is conducted in an atmosphere comprising air.

10. The method of claim 1, wherein the thermally curing of the polymerizable composition is conducted in an atmosphere comprising an inert gas at a concentration greater than is found in air.

11. The method of claim 1, wherein the polymerizable composition contains an amount of the phosphine-containing compound effective to reduce discoloration of the contact lens for at least 1 year when stored at room temperature, as compared to a second contact lens formed from a second polymerizable composition substantially identical to the first polymerizable composition except without the phosphine-containing compound and using a manufacturing process substantially identical to the manufacturing process of the hydrogel contact lens.

12. The method of claim 1, wherein the polymerizable composition further comprises at least one siloxane monomer.

13. The method of claim 1, wherein the reacting comprises cast molding the polymerizable composition in a contact lens mold assembly to form a polymeric lens body.

14. The method of claim 1, further comprising contacting the polymeric lens body with a washing liquid to remove extractable material from the polymeric lens body.

15. The method of claim 14, wherein the contacting removes a portion of the at least one phosphine compound from the polymeric lens body.

16. The method of claim 1, further comprising oxidizing at least a portion of the phosphine-containing compound present in the polymeric lens body, or in the hydrogel contact lens.

25. The method of claim 1, wherein said at least one phosphine-containing compound is not an initiator.

26. The method of claim 1, wherein the thermal initiator is 2,T-azobis-2-methyl propanenitrile, 2,2′

-azobis(2,4-dimethylpentanenitrile), 1,1′

-azo bis(cyanocyclohexane), or a combination thereof.

17. A hydrogel contact lens, comprising:

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

(a) at least one hydrophilic monomer, and

(b) at least one phosphine-containing compound, wherein the at least one phosphine-containing compound is present in an unoxidized form at the time it is combined with the at least one hydrophilic monomer in the polymerizable composition, and

(c) at least one thermal initiator that is thermally activated, wherein (b) and (c) are different from each other.

18. A batch of hydrogel contact lenses comprising a plurality of hydrogel contact lenses of claim 17.

19. The batch of hydrogel contact lenses of claim 18, wherein the batch of hydrogel contact lenses has an average axial edge lift (AEL) variance of less than plus or minus 50% over a time period from two weeks to seven years when stored at room temperature, or, when stored under accelerated shelf life conditions for a time period and temperature equivalent to storage from two weeks to seven years at room temperature, as determined based on at least 20 individual lenses of the batch, the AEP variance percentage determined for each of the individual lenses by the following equation (A):

((AEL_Final−

AEL_Initial)/AEL_Initial)×

100 

 

(A).

27. The hydrogel contact lens of claim 17, wherein the thermal initiator is 2,2′

-azobis-2-methyl propanenitrile, 2,2′

-azobis(2,4-dimethylpentanenitrile), 1,1′

-azo bis(cyanocyclohexane), or a combination thereof.

20. A hydrogel contact lens package, comprising:

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

(a) at least one hydrophilic monomer, and

(b) at least one phosphine-containing compound wherein the at least one phosphine-containing compound is present in an unoxidized form at the time it is combined with the at least one hydrophilic monomer in the polymerizable composition, and

(c) at least one thermal initiator that is thermally activated, wherein (b) and (c) are different from each other;

a packaging solution comprising a lens hydrating agent; and

a contact lens package base member having a cavity configured to hold the contact lens body and the packaging solution, and a seal attached to the base member configured to maintain the contact lens and the packaging solution in a sterile condition for a duration of time equivalent to a room temperature shelf life of the contact lens.

28. The hydrogel contact lens package of claim 20, wherein the thermal initiator is 2,2′

-azobis-2-methyl propanenitrile, 2,2′

-azobis(2,4-dimethylpentanenitrile), 1,1′

-azo bis(cyanocyclohexane), or a combination thereof.

21. A hydrogel contact lens, comprising:

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

(a) at least one hydrophilic monomer, and

(b) at least one phosphine-containing compound, wherein the at least one phosphine-containing compound is present in an unoxidized form at the time it is combined with the at least one hydrophilic monomer in the polymerizable composition and said at least one phosphine-containing compound is not an initiator, and

(c) at least one thermal initiator.

22. A batch of hydrogel contact lenses comprising a plurality of hydrogel contact lenses of claim 21.

23. The batch of hydrogel contact lenses of claim 22, wherein the batch of hydrogel contact lenses has an average axial edge lift (AEL) variance of less than plus or minus 50% over a time period from two weeks to seven years when stored at room temperature, or, when stored under accelerated shelf life conditions for a time period and temperature equivalent to storage from two weeks to seven years at room temperature, as determined based on at least 20 individual lenses of the batch, the AEP variance percentage determined for each of the individual lenses by the following equation (A):

((AEL_Final−

AEL_Initial)/AEL_Initial)×

100 

 

(A).

29. The hydrogel contact lens of claim 21, wherein the thermal initiator is 2,2′

-azobis-2-methyl propanenitrile, 2,2′

-azobis(2,4-dimethylpentanenitrile), 1,1′

-azo bis(cyanocyclohexane), or a combination thereof.

24. A hydrogel contact lens package, comprising:

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

(a) at least one hydrophilic monomer, and

(b) at least one phosphine-containing compound wherein the at least one phosphine-containing compound is present in an unoxidized form at the time it is combined with the at least one hydrophilic monomer in the polymerizable composition and said at least one phosphine-containing compound is not an initiator, and

(c) at least one thermal initiator, wherein (b) and (c) are different from each other;

a packaging solution comprising a lens hydrating agent; and

a contact lens package base member having a cavity configured to hold the polymeric lens body and the packaging solution, and a seal attached to the base member configured to maintain the contact lens and the packaging solution in a sterile condition for a duration of time equivalent to a room temperature shelf life of the contact lens.

30. The hydrogel contact lens package of claim 24, wherein the thermal initiator is 2,2′

-azobis-2-methyl propanenitrile, 2,2′

-azobis(2,4-dimethylpentanenitrile), 1,1′

-azobis(cyanocyclohexane), or a combination thereof.