Silicone hydrogels comprising N-vinyl amides and hydroxyalkyl (meth)acrylates or (meth)acrylamides

• US 9,494,714 B2
• Filed: 08/31/2015
• Issued: 11/15/2016
• Est. Priority Date: 12/23/2011
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Alli, Azaam, Vanderlaan, Douglas G., Ford, James D., Joslin, Scott L.
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): WHITELEY, JESSICA
• Application Number:
  US14/840,094
• Publication Number:
  US 20150369961A1
• Time in Patent Office: 442 Days
• Field of Search: 526/258, 526/72, 526/1, 520/1, 525/242, 525/55, 525/50, 525/313, 528/480
• US Class Current: 1/1
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08L 2203/02 for biomedical use
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

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.

Claims

1. A contact lens formed from a reaction mixture comprising,

(a) from 37 to 70 wt % of at least one slow reacting hydrophilic monomer selected from the group consisting of N-vinylamide monomers of Formula I, vinyl pyrrolidones of Formula II-IV, and N-vinyl piperidones of Formula V:

2. A contact lens of claim 1 wherein each R₃ is independently selected from ethyl and methyl groups.

3. A contact lens of claim 1 wherein all R₃ are methyl.

4. A contact lens of claim 1 wherein R₁₃ is selected from the group consisting of C₁-C₆ alkylene group which may be substituted with ether, hydroxyl and combinations thereof.

5. A contact lens of claim 1 wherein R₁₃ is selected from the group consisting of C₁ or C₃-C₆ alkylene groups which may be substituted with ether, hydroxyl and combinations thereof.

6. A contact lens of claim 1 wherein R₁₆ is H or methyl.

7. A contact lens of claim 1 wherein R₁₂ and each R₁₄ are methyl.

8. A contact lens of claim 1 wherein at least one R₁₄ is 3,3,3-trifluoropropyl.

9. A contact lens of claim 1 wherein R₁₆ is methyl or 2-hydroxyethyl.

10. A contact lens of claim 1 wherein a is 5 to 15.

11. A contact lens of claim 1 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, having a total number of carbon atoms in R₁ and R₂ of 4 or less.

12. A contact lens of claim 1 wherein the slow-reacting hydrophilic monomer is selected from a vinyl pyrrolidone of Formula III or IV and R₆ is methyl, R₇ is hydrogen, R₉ is CH═

CH₂, R₁₀ and R₁₁ are H.

13. A contact lens of claim 1 wherein 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.

14. A contact lens of claim 1 wherein the slow-reacting hydrophilic monomer is selected from the group consisting of N-vinylpyrrolidone, N-vinylacetamide, 1-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, and mixtures thereof.

15. A contact lens of claim 1 wherein the slow-reacting hydrophilic monomer is selected from the group consisting of NVP, VMA and 1-methyl-5-methylene-2-pyrrolidone.

16. A contact lens of claim 1 wherein the slow-reacting hydrophilic monomer comprises NVP.

17. A contact lens of claim 1 wherein R₁ is H or methyl, X is oxygen and R₁₇ is selected from C₂-C₄ mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 1-10 repeating units.

18. A contact lens of claim 1 wherein R₁ methyl, X is oxygen and R₁₇ is selected from C₂-C₄ mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 2-20 repeating units.

19. A contact lens of claim 1 wherein at least one R₁₄ is 3,3,3-trifluoropropyl.

20. A contact lens of claim 1 wherein R₁₃ is selected from C₁-C₆ alkylene groups which may be substituted with ether, hydroxyl and combinations thereof.

21. A contact lens of claim 1 wherein R₁₃ is selected from C₁ or C_3-6 alkylene groups which may be substituted with ether, hydroxyl and combinations thereof.

22. A contact lens of claim 1 wherein a is 7 to 30.

23. A contact lens of claim 1 wherein R₁₆ is H or methyl.

24. A contact lens of claim 1 wherein said mono (meth)acryloxyalkyl polydialkylsiloxane monomer is selected from the group consisting of monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, monomethacryloxypropyl terminated mono-n-methyl terminated polydimethylsiloxane, monomethacryloxypropyl terminated mono-n-butyl terminated polydiethylsiloxane, monomethacryloxypropyl terminated mono-n-methyl terminated polydiethylsiloxane, N-(2,3-dihydroxypropane)-N′

-(propyl tetra(dimethylsiloxy) dimethylbutylsilane)acrylamide;

α

-(2-hydroxy-1-methacryloxypropyloxypropyl)-ω

-butyl-octamethylpentasiloxane and mixtures thereof.

25. A contact lens of claim 1 wherein said mono (meth)acryloxyalkyl polydialkylsiloxane monomer is selected from the group consisting of monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, monomethacryloxypropyl terminated mono-n-methyl terminated polydimethylsiloxane, N-(2,3-dihydroxypropane)-N′

-(propyl tetra(dimethylsiloxy) dimethylbutylsilane)acrylamide.

26. A contact lens of claim 1 wherein R₁₇ is selected from the group consisting of 2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl.

27. A contact lens of claim 1 wherein said hydroxyalkyl monomer is selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1-hydroxypropyl-2-(meth)acrylate, 2-hydroxy-2-methyl-propyl (meth)acrylate, 3-hydroxy-2,2-dimethyl-propyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, glycerol (meth)acrylate, 2-hydroxyethyl (meth)acrylamide, polyethyleneglycol monomethacrylate, bis-(2-hydroxyethyl) (meth)acrylamide, 2,3-dihydroxypropyl (meth)acrylamide, and mixtures thereof.

28. A contact lens of claim 1 wherein said hydroxyalkyl monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxypropyl methacrylate, hydroxybutyl methacrylate, 3-hydroxy-2,2-dimethyl-propyl methacrylate, and mixtures thereof.

29. A contact lens of claim 1 wherein said hydroxyalkyl monomer comprises 2-hydroxyethyl methacrylate, 3-hydroxy-2,2-dimethyl-propyl methacrylate, glycerol methacrylate and mixtures comprising them.

30. A contact lens of claim 1 further comprising a Dk of at least about 60.

31. A contact lens of claim 1 further comprising a Dk of at least about 80.

32. A contact lens of claim 1 further comprising a water content of at least about 55%.

33. A contact lens of claim 1 further comprising a water content of at least about 60%.

34. A contact lens of claim 1 further comprising a contact angle of less than about 80°

.

35. A contact lens of claim 1 further comprising a % haze of less than about 50%.

36. A contact lens of claim 1 further comprising a % haze of less than about 10%.

37. A contact lens of claim 1 further comprising a modulus of less than about 120 psi.

38. A contact lens of claim 1 further comprising a modulus of about 100 psi or less.

39. A contact lens of claim 1 wherein the hydroxyalkyl monomer comprises 2,3-dihydroxypropyl methacrylate and the reaction mixture further comprises t-amyl alcohol as a diluent.

40. A contact lens of claim 1 wherein said reaction mixture further comprises at least one slow reacting crosslinker and at least one fast reacting crosslinker.

41. A contact lens of claim 40 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 0.05 to about 0.3 wt %.

42. A contact lens of claim 40 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 0.1 to about 0.2 wt %.

43. A contact lens of claim 1 wherein all components which comprise at least one hydroxyl group and a fast reacting reactive group are present in a concentration sufficient to provide a molar ratio of hydroxyl to silicon between about 0.16 and about 0.4.

44. A contact lens of claim 1 wherein said hydroxyalkyl (meth)acrylate or (meth)acrylamide monomers are present in a concentration sufficient to provide a HO:

Si ratio of 0.13 to 0.35.