Ionic silicone hydrogels having improved hydrolytic stability

• US 8,815,972 B2
• Filed: 05/21/2013
• Issued: 08/26/2014
• Est. Priority Date: 09/30/2008
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Rathore, Osman, Fadli, Zohra, Lada, Mark, Ford, James D., Alli, Azaam, Li, Yongcheng
• Primary Examiner(s): ZIMMER, MARC S
• Application Number:
  US13/898,919
• Publication Number:
  US 20130261215A1
• Time in Patent Office: 462 Days
• Field of Search: None
• US Class Current: 523/107
• CPC Class Codes: C08F 20/02 Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
• CPC Class Codes: C08F 20/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 22/16 Esters having free carboxylic acid groups
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/061 Polyesters; Polycarbonates
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 30/08 containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to ionic silicone hydrogel polymers displaying improved thermal stability. More specifically, the present invention relates to a polymer formed from reactive components comprising at least one silicone component and at least one ionic component comprising at least one anionic group. The polymers of the present invention display good thermal stability and desirable protein uptake.

Claims

1. A contact lens formed by polymerizing components comprising at least one silicone component and at least one ionic component wherein said ionic component is present in said polymer in concentration between 0.2 and 0.8 wt %, wherein all silicone components are free of trimethyl silyl groups;

and wherein said contact lens absorbs at least about 10 μ

g lysozyme, less than about 5 μ

g lipocalin and wherein at least about 50% of all proteins absorbed in or on said contact lens are in native form.

2. The contact lens of claim 1 wherein said ionic component comprises at least one polymerizable group and three to ten carbon atoms.

3. The contact lens of claim 1 where said ionic component comprises three to eight carbon atoms.

4. The contact lens of claim 1 wherein said ionic component comprises at least one carboxylic acid group.

5. The contact lens of claim 4 wherein said ionic component is selected from the group consisting of acrylic acid, methacrylic acid, furmaric acid, maelic acid, itaconic acid, crotonic acid, cinnamic acid, vinylbenzoic acid, monoesters of furmaric acid, maelic acid and itaconic acid and N-vinyloxycarbonyl alanine (N-vinyloxycarbonyl-β

-alanine) and homopolymers and copolymers thereof.

6. The contact lens of claim 1 wherein said contact lens absorbs at least about 50 μ

g lysozyme.

7. The contact lens of claim 1 wherein said contact lens absorbs at least about 100 μ

g lysozyme.

8. The contact lens of claim 1 wherein said contact lens absorbs at least about 200 μ

g lysozyme.

9. The contact lens of claim 1 wherein said contact lens absorbs at least about 500 μ

g lysozyme.

10. The contact lens of claim 1 wherein said contact lens absorbs at least about 800 μ

g lysozyme.

11. The contact lens of claim 1 wherein said contact lens absorbs about 3 μ

g or less lipocalin.

12. The contact lens of claim 1 wherein at least about 60% of all proteins absorbed in or on said contact lens are in native form.

13. The contact lens of claim 1 wherein at least about 75% of all proteins absorbed in or on said contact lens are in native form.

14. The contact lens of claim 1 further comprising a water content of at least about 15%.

15. The contact lens of claim 1 further comprising a Dk of at least about 50.

16. The contact lens of claim 5 wherein at least about 60% of all proteins absorbed in or on said contact lens are in native form.

17. The contact lens of claim 5 wherein at least about 75% of all proteins absorbed in or on said contact lens are in native form.

18. The contact lens of claim 1 wherein at least one silicone component is selected from compounds of Formula I:

19. The contact lens of claim 18 wherein said at least one silicone component is selected from the group consisting of monomethacryloxypropyl terminated mono-n-alkyl terminated polydialkylsiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane, methacryloxypropyl-terminated polydialkylsiloxane, mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-alkyl terminated polydialkylsiloxane and combinations thereof.

20. The polymer of claim 18 wherein said at least one silicone component is selected from monomethacryloxypropyl terminated mono-n-C_1-4 alkyl terminated polydimethylsiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane, and mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-C_1-4 alkyl terminated polydialkylsiloxane combinations thereof and the like.

21. The polymer of claim 18 wherein said at least one silicone component is selected from monomethacryloxypropyl-terminated mono-n-butyl terminated polydimethysiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane, methacryloxypropyl-terminated polydimethylsiloxane and mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydimethylsiloxane and mixtures thereof.

22. A contact lens formed by polymerizing components comprising at least one silicone component and at least one ionic component comprising at least one carboxylic acid group in molar concentrations up to about 9.3 mmol/100 gm, wherein all silicone components are free of trimethyl silyl groups, and wherein said contact lens absorbs at least about 10 μ

g lysozyme, less than about 5 μ

g lipocalin and wherein at least about 50% of proteins absorbed in or on said contact lens are in native form.

23. The contact lens of claim 22 wherein said ionic component comprises at least one polymerizable group and three to ten carbon atoms.

24. The contact lens of claim 23 where said ionic component comprises three to eight carbon atoms.

25. The contact lens of claim 22 wherein said ionic component is selected from the group consisting of acrylic acid, methacrylic acid, furmaric acid, maelic acid, itaconic acid, crotonic acid, cinnamic acid, vinylbenzoic acid, monoesters of furmaric acid, maelic acid and itaconic acid and N-vinyloxycarbonyl alanine (N-vinyloxycarbonyl-β

-alanine) and homopolymers and copolymers thereof.

26. The contact lens of claim 22 wherein said contact lens absorbs at least about 50 μ

g lysozyme.

27. The contact lens of claim 22 wherein said contact lens absorbs at least about 100 μ

g lysozyme.

28. The contact lens of claim 22 wherein said contact lens absorbs at least about 200 μ

g lysozyme.

29. The contact lens of claim 22 wherein said contact lens absorbs at least about 500 μ

g lysozyme.

30. The contact lens of claim 22 wherein said contact lens absorbs at least about 800 μ

g lysozyme.

31. The contact lens of claim 22 wherein said contact lens absorbs about 3 μ

g or less lipocalin.

32. The contact lens of claim 22 wherein at least about 60% of all proteins absorbed in or on said contact lens are in native form.

33. The contact lens of claim 22 wherein at least about 75% of all proteins absorbed in or on said contact lens are in native form.

34. The contact lens of claim 22 further comprising a water content of at least about 15%.

35. The contact lens of claim 22 further comprising a contact angle of less than about 90°

.

36. The contact lens of claim 35 wherein at least about 60% of all proteins absorbed in or on said contact lens are in native form.

37. The contact lens of claim 35 wherein at least about 75% of all proteins absorbed in or on said contact lens are in native form.

38. The contact lens of claim 22 wherein at least one silicone component is selected from compounds of Formula I:

39. The contact lens of claim 22 wherein said at least one silicone component is selected from the group consisting of monomethacryloxypropyl terminated mono-n-alkyl terminated polydialkylsiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane, methacryloxypropyl-terminated polydialkylsiloxane, mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-alkyl terminated polydialkylsiloxane and combinations thereof.

40. The contact lens of claim 22 wherein said at least one silicone component is selected from monomethacryloxypropyl terminated mono-n-C_1-4alkyl terminated polydimethylsiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane, and mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-C_1-4 alkyl terminated polydialkylsiloxane combinations thereof.

41. The contact lens of claim 22 wherein said at least one silicone component is selected from monomethacryloxypropyl-terminated mono-n-butyl terminated polydimethysiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane, methacryloxypropyl-terminated polydimethylsiloxane and mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydimethylsiloxane and mixtures thereof.