Ionic silicone hydrogels

Patent metadata

Field	Value
Publication number	US-9507055-B2
Application number	US-201514828560-A
Country	US
Kind code	B2
Filing date	Aug 18, 2015
Priority date	Dec 23, 2011
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

The present invention relates to a process comprising the steps of reacting a reactive mixture comprising at least one silicone-containing component, at least one hydrophilic component, and at least one diluent to form an ophthalmic device having an advancing contact angle of less than about 80°; and contacting the ophthalmic device with an aqueous extraction solution at an elevated extraction temperature, wherein said at least one diluent has a boiling point at least about 10° higher than said extraction temperature.

First claim

What is claimed is:

1. A silicone hydrogel contact lens formed from a reaction mixture comprising
about 37 to about 75 wt % of a mixture of slow-reacting hydrophilic monomers, each having a slow-reacting hydrophilic monomer kinetic half life; said mixture of slow reacting hydrophilic monomers comprising and at least one slow-reacting ionic monomer;
at least one silicone-containing component having a silicone-containing component kinetic half life, which may be optionally substituted with at least one hydroxyl containing group; and
at least one hydroxyl-containing component selected from said silicone-containing components substituted with at least one hydroxyl containing group, at least one hydroxyalkyl monomer, and mixtures thereof,
wherein ratio of each of said slow-reacting hydrophilic component half lives to said silicone-containing component half life is at least 2, and said contact lens uptakes at least about 30 μg, of lysozyme from a 2 mg/ml lysozyme solution over 72 hours incubation at 35° C.

2. The silicone hydrogel contact lens of claim 1 wherein said slow-reacting ionic component is selected from the group consisting of anionic components, cationic components, zwitterionic components and mixtures thereof.

3. The silicone hydrogel contact lens of claim 1 wherein said slow-reacting ionic component comprise at least one anionic component selected from the group consisting of carboxylic acids, sulfonic acids, boronic acids, phosphonic acids and their salts and mixtures thereof.

4. The silicone hydrogel contact lens of claim 1 wherein said slow-reacting ionic component comprises reactive functionality selected from the group consisting of ionic vinyl ethers, ionic vinyl amines and ionic vinyl enamines.

5. The silicone hydrogel contact lens of claim 1 wherein said slow-reacting ionic component is selected from the group consisting of N-vinyloxycarbonyl-α-alanine; N-vinyloxycarbonyl-β-alanine (VINAL); 2-vinyl-4,4-dimethyl-2-oxazolin-5-one (VDMO); vinyl sulphonate sodium salt; acetic acid, 2-carboxymethoxy)-,1-ethenylesters of Formula Q, mixtures thereof and the like.

6. The silicone hydrogel contact lens of any of claims 1 - 4 wherein said slow-reacting ionic component is present in the reactive mixture in an amount below about 20 mole %.

7. The silicone hydrogel contact lens of any of claims 1 - 4 wherein said slow-reacting ionic component is present in the reactive mixture in an amount between about 0.5 and about 15 mole %, based upon all components in the reaction mixture.

8. The silicone hydrogel contact lens of any of claims 1 - 4 wherein said slow-reacting ionic component is present in the reactive mixture in an amount between about 0.5 and about 5 mole %, based upon all components in the reaction mixture.

9. The silicone hydrogel contact lens of any of claims 1 - 4 wherein said slow-reacting ionic component is present in the reactive mixture in an amount between about 0.5 and about 10 mole %, based upon all components in the reaction mixture.

10. The silicone hydrogel contact lens of claim 1 wherein all of said slow-reacting components have the same reactive functionality.

11. The silicone hydrogel contact lens of claim 1 wherein all of said slow-reacting components have vinyl functionality.

12. The silicone hydrogel contact lens of claim 1 wherein said reaction mixture further comprises at least one slow reacting crosslinker and at least one fast reacting crosslinker.

13. The silicone hydrogel contact lens of claim 12 wherein said slow reacting crosslinkers have only vinyl reactive functionality and said fast reacting crosslinkers have (meth)acrylate reactive functionality only.

14. The silicone hydrogel contact lens of claim 12 wherein said slow reacting crosslinker comprises TAC and said fast reacting crosslinker is selected from the group consisting of EDGMA, TEGDMA and mixtures thereof.

15. The silicone hydrogel contact lens of claim 12 wherein said at least one slow reacting crosslinker and at least one fast reacting crosslinker are each present in said reaction mixture in amounts between about 0.4 to about 2.0 mmoles per 100 g of reactive components.

16. The silicone hydrogel contact lens of claim 12 wherein said at least one slow reacting crosslinker and at least one fast reacting crosslinker are each present in said reaction mixture in amounts between about 0.3 to about 2.0 mmol/100 g of polymerizable components.

17. The silicone hydrogel contact lens of claim 1 wherein said reactive mixture further comprises at least one reactive cationic component.

18. The silicone hydrogel contact lens of claim 17 wherein said cationic component or hydrogen bonding component is present in an amount sufficient to improve surface resilience of said hydrogel.

19. The silicone hydrogel contact lens of claim 17 wherein said at least one reactive cationic component has the same reactive functionality as at least one of said silicone containing components.

20. The silicone hydrogel contact lens of claim 1 wherein said kinetic half life ratio is at least about 3.

21. The silicone hydrogel contact lens of claim 1 further comprising a Dk of at least about 80.

22. The silicone hydrogel contact lens of claim 1 further comprising a water content of at least about 55%.

23. The silicone hydrogel contact lens of claim 1 further comprising a modulus of about 100 psi or less.

24. The silicone hydrogel contact lens of claim 1 wherein said reaction mixture further comprises at least one UV absorbing compound.

25. The silicone hydrogel contact lens of claim 24 wherein said at least one UV absorbing compound is reactive.

26. The silicone hydrogel contact lens The silicone hydrogel of claim 24 wherein said at least one UV absorbing compound is selected from benzotriazoles.

27. The silicone hydrogel contact lens of claim 24 wherein said at least one UV absorbing compound is selected from the group consisting of reactive 2-(2′-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, 2-hydroxyphenyltriazines, oxanilides, cyanoacrylates, salicylates and 4-hydroxybenzoates.

28. The silicone hydrogel contact lens of claim 24 wherein said at least one UV absorbing compound is selected from the group consisting of 2-(2′-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, 5-vinyl and 5-isopropenyl derivatives of 2-(2,4-dihydroxyphenyl)-2H-benzotriazole and 4-acrylates or 4-methacrylates of 2-(2,4-dihydroxyphenyl)-2H-benzotriazole or 2-(2,4-dihydroxyphenyl)-1,3-2H-dibenzotriazole, and mixtures thereof.

29. The silicone hydrogel contact lens of claim 14 comprising between about 0.5 and about 4 wt. %, of at least one UV absorber.

30. The silicone hydrogel contact lens of claim 24 comprising between about 1 wt % and about 2 wt % UV absorber.

31. The silicone hydrogel contact lens of claim 1 wherein said reaction mixture is substantially free of diluent.

32. The silicone hydrogel contact lens of claim 1 wherein said reaction mixture is substantially free of TRIS.

33. The silicone hydrogel contact lens of claim 1 wherein said slow-reacting hydrophilic monomer comprises a reactive group selected from the group consisting of (meth)acrylamides, vinyls, allyls and combinations thereof and said silicone-containing component comprises a reactive group selected from the gro

Assignees

• Johnson & Johnson Vision Care

Inventors

• Alli Azaam
• Ford James D
• Vanderlaan Douglas G
• Joslin Scott L

Classifications

• C08L83/04

  Polysiloxanes · CPC title

• C08L101/14

  the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels · CPC title

• C08L33/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title