Silicone hydrogels having a structure formed via controlled reaction kinetics

Patent metadata

Field	Value
Publication number	US-9994665-B2
Application number	US-201715398830-A
Country	US
Kind code	B2
Filing date	Jan 5, 2017
Priority date	Dec 23, 2011
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

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 process for forming a silicone hydrogel comprising photocuring a reaction mixture comprising about 39 to about 75 wt % of at least one slow-reacting hydrophilic monomer;
at least one silicone-containing component;
at least one photoinitiator; and
optional additional hydrophilic components;
wherein said photocuring is completed in about 30 minutes or less and at least one of said silicone-containing component, optional additional hydrophilic components or both comprises at least one hydroxyl group.

2. The process of claim 1 wherein said reaction mixture further comprises at least one UV absorbing compound.

3. The process of claim 2 wherein said at least one UV absorbing compound is selected from benzotriazoles.

4. The process of claim 2 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.

5. The process of claim 2 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.

6. The process of claim 2 comprising between about 0.5 and about 4 wt. %, of at least one UV absorber.

7. The process of claim 2 comprising between about 1 wt % and about 2 wt % UV absorber.

8. The process of claim 1 wherein said reaction mixture is free of diluent.

9. The process of claim 1 wherein said reaction mixture is free of TRIS.

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

11. The process 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.

12. The process 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.

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

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

15. The process 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.

16. The process 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.

17. The process 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 acid combinations thereof.

18. The process of claim 1 wherein said slow reacting hydrophilic monomer is selected from N-vinylamide monomer of Formula I, a vinyl pyrrolidone of Formula II-IV, 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 .

19. The process of claim 18 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.

20. The process of claim 18 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.

21. The process 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.

22. The process of claim 1 wherein the slow-reacting hydrophilic monomer is selected from NVP, VMA and 1-methyl-5-methylene-2-pyrrolidone.

23. The process of claim 1 wherein the slow-reacting hydrophilic monomer comprises NVP.

24. The process of claim 1 wherein said silicone-containing component comprises at least one hydroxyl group.

25. The process of claim 1 further comprising at least one hydroxyalkyl monomer.

26. The process of claim 25 wherein said hydroxyalkyl monomer is selected from hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer of Formula VII or a styryl compound of Formula VIII

wherein R 1 is H or methyl,
X is O or NR 16 , R 16 is a H, C 1 to C 4 alkyl, which may be further substituted with at least one OH, and
R 17 is selected from C 2 -C 4 mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 1-10 repeating units.

27. The process of claim 26 wherein R 1 is H or methyl, X is oxygen and R is selected from C 2 -C 4 mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 1-10 repeating units.

28. The process of claim 26 wherein R 1 methyl, X is oxygen and R is selected from C 2 -C 4 mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 2-20 repeating units.

29. The process of claim 26 wherein said hydroxyalkyl monomer is selected from 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1-hydroxypropyl-2-(m

Assignees

• Johnson & Johnson Vision Care

Inventors

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

Classifications

• C08L83/04

  Polysiloxanes · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08F2/50

  with sensitising agents · CPC title

• A61F2/142

  Cornea, e.g. artificial corneae, keratoprostheses or corneal implants for repair of defective corneal tissue · CPC title