Ionic silicone hydrogels having improved hydrolytic stability

Patent metadata

Field	Value
Publication number	US-9260544-B2
Application number	US-201414301633-A
Country	US
Kind code	B2
Filing date	Jun 11, 2014
Priority date	Sep 30, 2008
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

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.

First claim

We claim:

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:

wherein b=2 to 20; one terminal R 1 comprises at least one ethylenically unsaturated moiety, the remaining terminal R 1 are independently selected from the group consisting of monovalent alkyl groups having 2 to 16 carbon atoms, and the remaining R 1 are selected from the group consisting of monovalent alkyl groups having 1 to 16 carbon atoms, wherein said polymer absorbs at least about 10 μg lysozyme and less than about 5 μg lipocalin.

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 μg lysozyme.

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

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

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

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

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

Assignees

• Johnson & Johnson Vision Care

Inventors

• Rathore Osman
• Fadli Zohra
• Lada Mark
• Ford James D
• Alli Azaam
• Li Yongcheng

Classifications

• C08F290/06 Primary

  Polymers provided for in subclass C08G · CPC title

• G02B1/043

  Contact lenses · CPC title

• C08F20/06 Primary

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08L51/085

  on to polysiloxanes · CPC title

• C08F22/16

  Esters having free carboxylic acid groups · CPC title