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

• US 9,964,666 B2
• Filed: 09/28/2016
• Issued: 05/08/2018
• 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): WHITELEY, JESSICA
• Application Number:
  US15/278,691
• Publication Number:
  US 20170017016A1
• Time in Patent Office: 587 Days
• Field of Search: 526258, 526 71, 526 1, 520 1, 525242, 525 55, 525 50, 525313, 528480
• 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 silicone hydrogel formed from a reaction mixture comprising,

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

2. The silicone hydrogel of claim 1 wherein each R₃ is independently selected from ethyl and methyl groups.

3. The silicone hydrogel of claim 1 wherein all R₃ are methyl.

4. The silicone hydrogel 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. The silicone hydrogel 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. The silicone hydrogel of claim 1 wherein R₁₆ in Formula VII is H or methyl.

7. The silicone hydrogel of claim 1 wherein R₁₂ and each R₁₄ are methyl.

8. The silicone hydrogel of claim 1 wherein at least one R₁₄ is 3,3,3-trifluoropropyl.

9. The silicone hydrogel of claim 1 wherein R₄ is CH₂.

10. The silicone hydrogel 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.

11. The silicone hydrogel 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.

12. The silicone hydrogel 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.

13. The silicone hydrogel of claim 1 wherein the slow-reacting hydrophilic monomer comprises NVP.

14. The silicone hydrogel of claim 1 wherein at least one R₁₄ is 3,3,3-trifluoropropyl.

15. The silicone hydrogel of claim 1 wherein R₁₃ is selected from C₁-C₆ alkylene groups which may be substituted with ether, hydroxyl and combinations thereof.

16. The silicone hydrogel 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.

17. The silicone hydrogel of claim 1 wherein a is 7 to 30.

18. The silicone hydrogel of claim 1 wherein R₁₆ in Formula IX is H or methyl.

19. The silicone hydrogel 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.

20. The silicone hydrogel 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.

21. The silicone hydrogel of claim 1 wherein in Formula IX 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.

22. The silicone hydrogel of claim 1 wherein in Formula IX R₁ is 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.

23. The silicone hydrogel of claim 1 wherein R₁₇ is 2-hydroxyethyl, 2,3-dihydroxypropyl, or 2-hydroxypropyl.

24. The silicone hydrogel of claim 1 wherein Formula IX 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.

25. The silicone hydrogel of claim 1 wherein Formula IX 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.

26. The silicone hydrogel of claim 1 wherein Formula IX comprises 2-hydroxyethyl methacrylate, 3-hydroxy-2,2-dimethyl-propyl methacrylate, glycerol methacrylate and mixtures comprising them.

27. The silicone hydrogel of claim 1 further comprising a Dk of at least about 60.

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

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

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

31. The silicone hydrogel of claim 1 further comprising an advancing contact angle of less than about 80°

.

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

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

34. The silicone hydrogel of claim 1 further comprising a modulus of less than about 120 psi.

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

36. The silicone hydrogel of claim 1 wherein Formula IX comprises 2,3-dihydroxypropyl methacrylate and the reaction mixture further comprises t-amyl alcohol as a diluent.

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

38. The silicone hydrogel of claim 37 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.

39. The silicone hydrogel of claim 37 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 %.