Ionic silicone hydrogels having improved hydrolytic stability

• US 9,260,544 B2
• Filed: 06/11/2014
• Issued: 02/16/2016
• 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:
  US14/301,633
• Publication Number:
  US 20140296440A1
• Time in Patent Office: 615 Days
• Field of Search: None
• US Class Current: 1/1
• 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 polymer formed from reactive components comprising about 0.2 to about 0.8 weight % of at least one anionic component and at least one silicone component selected from the group consisting of reactive polydialkylsiloxane selected from compounds of Formula I:

2. The polymer of claim 1 wherein said at least one silicone component is selected from monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane, and mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane combinations thereof and the like.

3. The polymer of claim 1 wherein said anionic component is a carboxylic acid containing component selected from the group consisting of free radical reactive carboxylic acids comprising 1-8 carbon atoms.

4. The polymer of claim 3 wherein said carboxylic acid-containing component is selected from the group consisting of (meth)acrylic acid, acrylic acid, itaconic acid, crotonic acid, cinnamic acid, vinylbenzoic acid, fumaric acid, maleic acid, N-vinyloxycarbonyl alanine and mixtures thereof.

5. The polymer of claim 3 wherein said carboxylic acid-containing component comprises methacrylic acid.

6. The polymer of claim 1 wherein at least about 50% of all proteins absorbed in or on said polymer are in native form.

7. The polymer of claim 1 wherein said anionic component comprises at least one polymerizable group and three to ten carbon atoms.

8. The polymer of claim 1 wherein said anionic component comprises three to eight carbon atoms.

9. The polymer of claim 1 wherein said anionic component comprises at least one carboxylic acid group.

10. The polymer of claim 1 wherein said anionic 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.

11. The polymer of claim 1 wherein said polymer absorbs at least about 50 μ

g lysozyme.

12. The polymer of claim 1 wherein said polymer absorbs at least about 100 μ

g lysozyme.

13. The polymer of claim 1 wherein said polymer absorbs at least about 200 μ

g lysozyme.

14. The polymer of claim 1 wherein said polymer absorbs at least about 500 μ

g lysozyme.

15. The polymer of claim 1 wherein said polymer absorbs at least about 800 μ

g lysozyme.

16. The polymer of claim 1 wherein said polymer absorbs about 3 μ

g or less lipocalin.

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

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

19. The polymer of claim 1 further comprising a water content of at least about 15%.

20. The polymer of claim 1 further comprising a Dk of at least about 50.

21. The polymer of claim 1 further comprising a contact angle of less than about 90°

.