Silicone hydrogels having a structure formed via controlled reaction kinetics

Patent metadata

Field	Value
Publication number	US-9562161-B2
Application number	US-201414495264-A
Country	US
Kind code	B2
Filing date	Sep 24, 2014
Priority date	Dec 23, 2011
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

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 formed from a reaction mixture comprising
about 39 to about 75 wt % of at least one slow-reacting hydrophilic monomer;
at least one silicone-containing component; and
at least one visible light photoinitiator;
wherein at least one of said silicone-containing component, optional additional hydrophilic components or both comprises at least one hydroxyl group and wherein said slow-reacting hydrophilic component and said silicone-containing component are selected to have a conversion ratio at 90% conversion of at least about 20.

2. The silicone hydrogel of claim 1 wherein said slow-reacting hydrophilic monomer has a slow-reacting hydrophilic monomer kinetic half life;
said at least one silicone-containing component has a silicone-containing component kinetic half life, and a ratio of said slow-reacting hydrophilic component half life to said silicone-containing component half life is at least about 3.

3. The silicone hydrogel of claim 1 wherein said kinetic half life ratio is at least about 5.

4. The silicone hydrogel of claim 1 further comprising a Dk of at least about 80.

5. The silicone hydrogel of claim 1 further comprising a Dk of at least about 85.

6. The silicone hydrogel of claim 1 further comprising a % haze of less than about 50%.

7. The silicone hydrogel of claim 1 further comprising a % haze of less than about 10%.

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

9. The silicone hydrogel of claim 1 further comprising a water content of at least about 60%.

10. The silicone hydrogel of claim 1 further comprising a modulus of less than about 150 psi.

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

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

13. The silicone hydrogel of claim 12 wherein said at least one UV absorbing compound is selected from benzotriazoles.

14. The silicone hydrogel of claim 12 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.

15. The silicone hydrogel of claim 12 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.

16. The silicone hydrogel of claim 12 comprising between about 0.5 and about 4 wt. %, of at least one UV absorber.

17. The silicone hydrogel of claim 12 comprising between about 1 wt % and about 2 wt % UV absorber.

18. The silicone hydrogel of claim 1 wherein said reaction mixture is substantially free of diluent.

19. The silicone hydrogel of claim 1 wherein said reaction mixture is substantially free of TRIS.

20. The silicone hydrogel of claim 1 wherein said reaction mixture is substantially free of silicone containing macromers or prepolymers.

21. The silicone hydrogel 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 group consisting of (meth)acrylates, styryls, amides and mixtures thereof.

22. The silicone hydrogel of claim 1 wherein said slow-reacting hydrophilic monomer comprises a reactive group selected from the group consisting of vinyls, allyls and combinations thereof and said silicone-containing component comprises a reactive group selected from the group consisting of (meth)acrylates, styryls, amides and mixtures thereof.

23. The silicone hydrogel of claim 1 wherein said slow-reacting hydrophilic monomer is present in an amount between about 39 and about 70 wt %.

24. The silicone hydrogel of claim 1 wherein said slow-reacting hydrophilic monomer is present in an amount between about 39 and about 60 wt %.

25. The silicone hydrogel of claim 1 wherein said slow-reacting hydrophilic monomer comprises a reactive group selected from the group consisting of N-vinyl amides, O-vinyl carbamates, O-vinyl carbonates, N-vinyl carbamates, O-vinyl ethers, O-2-propenyl, wherein the vinyl or allyl groups may be further substituted with a methyl group.

26. The silicone hydrogel of claim 1 wherein said slow reacting hydrophilic monomer comprises at least one hydrophilic group selected from the group consisting of hydroxyls, amines, ethers, amides, ammonium groups, carboxylic acid, carbamates and combinations thereof.

27. The silicone hydrogel of claim 1 wherein said slow reacting hydrophilic monomer comprises at least one hydrophilic group selected from the group consisting of hydroxyls, ethers, amides, carboxylic acids, and combinations thereof.

28. The silicone hydrogel of claim 1 wherein said slow reacting hydrophilic monomer is selected from N-vinylamide monomer of Formula I, a vinyl pyrrolidone of Formula II-1V, n-vinyl piperidone of Formula V:

wherein R is H or methyl;
R 1 , R 2 , R 3 , R 6 , R 7 , R 10 , and R 11 are independently selected from H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , C(CH 3 ) 2 ;
R 4 and R 8 are independently selected from CH 2 , CHCH 3 and C(CH 3 );
R 5 is selected from H, methyl, ethyl; and
R 9 is selected from CH═CH 2 , CCH 3 ═CH 2 , and CH═CHCH 3 .

29. The silicone hydrogel of claim 28 wherein the slow-reacting hydrophilic monomer is selected from the vinyl pyrrolidone of Formula II or IV or the N-vinyl amide monomer of Formula I, and the total number of carbon atoms in R 1 and R 2 is 4 or less.

30. The silicone hydrogel of claim 28 wherein the slow-reacting hydrophilic monomer is selected from a vinyl pyrrolidone of Formula III or IV and R 6 is methyl, R 7 is hydrogen, R 9 is CH═CH 2 , R 10 and R 11 are H.

31. The silicone hydrogel of claim 1 wherein the slow-reacting hydrophilic monomer is selected from the slow-reacting hydrophilic monomer is selected from ethylene glycol vinyl ether (EGVE), di(ethylene glycol) vinyl ether (DEGVE), N-vinyl pyrrolidone (NVP), 1-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone; 1-ethyl-5-methylene-2-pyrrolidone, N-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, N-vinyl-N-methyl acetamide (VMA), N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, allyl alcohol, N-vinyl caprolactam, N-2-hydroxyethyl vinyl carbamate, N-carboxy-β-alanine N-vinyl ester; N-carboxyvinyl-β-alanine (VINAL), N-carboxyvinyl-α-alanine and mixtures thereof.

32. The silicone hydrogel of claim 1 wherein the

Assignees

• Johnson & Johnson Vision Care

Inventors

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

Classifications

• G02C7/049

  Contact lenses having special fitting or structural features achieved by special materials or material structures · CPC title

• B29C59/16

  by wave energy or particle radiation {, e.g. infrared heating (B29C59/007 takes precedence)} · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C08F20/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C08L77/02

  Polyamides derived from omega-amino carboxylic acids or from lactams thereof (C08L77/10 takes precedence) · CPC title