Forming clear, wettable silicone hydrogel articles without surface treatments

• US 8,158,695 B2
• Filed: 03/05/2004
• Issued: 04/17/2012
• Est. Priority Date: 09/06/2002
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Vanderlaan, Douglas G., Petisce, James R., Alli, Azaam, McCabe, Kevin P.
• Primary Examiner(s): Cain, Edward J
• Application Number:
  US10/794,399
• Publication Number:
  US 20100280146A1
• Time in Patent Office: 2,965 Days
• Field of Search: 523113-116
• US Class Current: 523/113
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

The present invention is a composition, which may be used to form contact lenses, comprising at least one silicone containing component, at least one hydrophilic component, at least one high molecular weight hydrophilic polymer and at least one diluent with an alpha value of about 0.5 to about 1 and a Hansen solubility parameter of less than about 10.

Claims

1. A composition comprising:

at least one silicone containing component,

at least one hydrophilic component,

at least one high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, wherein the composition forms a clear blend at a selected reaction temperature, wherein the reaction temperature is up to about 75C., and wherein the composition further comprises at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the blend absent the diluent.

2. The composition of claim 1 wherein the alpha value is between about 0.1 and about 0.9.

3. The composition of claim 1 wherein the hydrophilic component and the silicone containing component are polymerizable and the composition forms a clear article when polymerized at the reaction temperature.

4. The composition of claim 1 wherein the diluent is selected from the group consisting of alcohols having at least three carbon atoms.

5. The composition of claim 1 wherein the diluent is selected from the group consisting of alcohols having at least four carbon atoms.

6. The composition of claim 1 wherein the diluent is selected from the group consisting of alcohols having at least six carbon atoms.

7. The composition of claim 1 wherein the δ

p of less than about 6.

8. The composition of claim 1 wherein the silicone containing compatibilizing component is present in an amount between about 0 and about 5 weight % of the composition.

9. The composition of claim 1 wherein diluent is one or more selected from the group consisting of 1-ethoxy-2-propanol, diisopropylaminoethanol, isopropanol, 3,7-dimethyl-3-octanol, 1-decanol, 1-dodecanol, 1-octanol, 1-pentanol, 2-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, tert-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-propanol, 1-propanol, ethanol, 2-ethyl-1-butanol, SiGMA acetate, 1-tert-butoxy-2-propanol, 3,3-dimethyl-2-butanol, tert-butoxyethanol, 2-octyl-1-dodecanol, decanoic acid, octanoic acid, dodecanoic acid, 2-(diisopropylamino)ethanol and mixtures thereof.

10. The composition of claim 1 wherein the diluent is one or more selected from the group consisting of 3,7-dimethyl-3-octanol, 1-dodecanol, 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, 2-pentanol, t-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, ethanol, 3,3-dimethyl-2-butanol, 2-octyl-1-dodecanol, decanoic acid, octanoic acid, dodecanoic acid and mixtures thereof.

11. The composition of claim 1 wherein the diluent is one or more selected from the group consisting of 3,7-dimethyl-3-octanol, 1-dodecanol, 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 1-dodecanol, 3-methyl-3-pentanol, 1-pentanol, 2-pentanol, t-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, 3,3-dimethyl-2-butanol, 2-octyl-1-dodecanol and mixtures thereof.

12. The composition of claim 1 wherein the high molecular weight hydrophilic polymer has a molecular weight greater than about 150,000 Daltons.

13. The composition of claim 1 wherein the high molecular weight hydrophilic polymer has a molecular weight between about 150,000 to about 2,000,000 Daltons.

14. The composition of claim 1 wherein the high molecular weight hydrophilic polymer has a molecular weight between about 500,000 to about 1,500,000 Daltons.

15. The composition of claim 1 wherein the high molecular weight hydrophilic polymer is present in an amount between about 1 to about 15 weight % of the composition.

16. The composition of claim 1 wherein the high molecular weight hydrophilic polymer is present in an amount between about 3 to about 12 weight % of the composition.

17. The composition of claim 1 wherein the high molecular weight hydrophilic polymer comprises a cyclic amide in a backbone of the high molecular weight hydrophilic polymer.

18. The composition of claim 1 wherein the high molecular weight hydrophilic polymer comprises a cyclic imide in a backbone of the high molecular weight hydrophilic polymer.

19. The composition of claim 1 wherein the high molecular weight hydrophilic polymers is one or more selected from the group consisting of poly-N-vinyl pyrrolidone, poly-N-vinyl-2- piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2- caprolactam, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N-vinyl-3-ethyl-2- pyrrolidone, and poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinylimidazole, poly-N-N-dimethylacrylamide, polyvinyl alcohol, polyacrylic acid, polyethylene oxide, poly 2 ethyl oxazoline, heparin polysaccharides, polysaccharides, and mixtures, block copolymers, random copolymers, branched copolymers, multichain copolymers, comb-shaped copolymers, and star shaped copolymers thereof.

20. The composition of claim 1 wherein the high molecular weight hydrophilic polymer comprises poly-N-vinylpyrrolidone.

21. The composition of claim 1 wherein the reaction temperature is about 40°

C.

22. The composition of claim 1 wherein at least one component comprises a least one hydrogen bond donor group and at least one component comprises at least one hydrogen bond acceptor group and said composition comprises a ratio of moles hydrogen bond donor groups to moles of hydrogen bond acceptor groups in said high molecular weight hydrophilic polymer is ≧

about 0.8 for the composition.

23. The composition of claim 1 wherein at least one component comprises a least one hydrogen bond donor group, said silicone containing component comprises silicon and said composition comprises a ratio of moles of hydrogen bond donor group to moles of silicon greater than about 0.14 for the composition.

24. A composition comprising

at least one silicone containing component,

at least one hydroxyl containing component,

at least one high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, wherein the composition forms a clear blend at a selected reaction temperature, wherein the reaction temperature is up to about 75°

C., wherein the composition further comprises at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the blend absent the diluent.

25. The composition of claim 24 wherein the hydroxyl containing component comprises at least one polymerizable double bond and at least one hydrophilic functional group.

26. The composition of claim 25 wherein the polymerizable double bond is one or more selected from the group consisting of acrylic, methacrylic, acrylamido, methacrylamido, fumaric, maleic, styryl, isopropenylphenyl, O-vinylcarbonate, O-vinylcarbamate, allylic, O-vinylacetyl and N-vinyllactam and N-vinylamido double bonds.

27. The composition of claim 24 wherein the hydroxyl containing component is one or more selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylamide, 2-hydroxyethyl acrylamide, 2-hydroxyethyl vinyl carbamate, 2-hydroxyethyl vinyl carbonate, 2-hydroxypropyl methacrylate, hydroxyhexyl methacrylate, hydroxyoctyl methacrylate and mixtures thereof.

28. The composition of claim 24 wherein the hydroxyl containing component comprises 2-hydroxyethyl methacrylate.

29. The composition of claim 24 wherein the silicone containing component comprises a fluoroether-siloxane-methacrylate macromer.

30. The composition of claim 25 or 29 wherein the hydroxyl containing component comprises 2-hydroxyethyl methacrylate and

the high molecular weight hydrophilic polymer comprises poly-N-vinylpyrrolidone.

31. The composition of claim 25 wherein the silicone containing component comprises monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane.

32. The composition of claim 31 wherein the hydroxyl containing component comprises 2-hydroxyethyl methacrylate and

the high molecular weight hydrophilic polymer comprises poly-N-vinylpyrrolidone.

33. The composition of claim 24 wherein the reaction temperature is about 40°

C.

34. A composition comprising

about 1 part by weight of at least one silicone containing component,

about 1.6 parts by weight of at least one hydrophilic component,

about 0.3 parts by weight of at least one high molecular weight hydrophilic polymer and

about 2 parts by weight diluent, and the composition is a compatible mixture at about room temperature.

35. The composition of claim 34 wherein the hydrophilic component comprises

DMA,

the silicone containing component comprises monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, and

the high molecular weight hydrophilic polymer comprises PVP.

36. An ophthalmic device comprising a cured compound, wherein the compound in precure form comprises

at least one silicone containing component,

at least one hydrophilic component,

at least one high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, wherein the procure form further comprises at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the blend absent the diluent.

37. An ophthalmic device comprising a cured compound, wherein the compound in precure form comprises

at least one silicone containing component,

at least one hydroxyl containing component,

at least high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, wherein the procure form further comprises at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the blend absent the diluent.

38. A method of making a clear and wettable ophthalmic device comprising

Forming a reaction mixture comprising at least one silicone containing component, at least one hydrophilic component, at least one high molecular weight hydrophilic polymer, at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10 and at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the reaction mixture absent the diluent,

Placing the reaction mixture in a mold,

Curing the reaction mixture to form the ophthalmic device,

Releasing the ophthalmic device from the mold, and

Removing substantially all of the diluent from the ophthalmic device.

39. A method of making a clear and wettable ophthalmic device comprising

Forming a reaction mixture comprising at least one silicone containing component, at least one hydroxyl containing component, at least one high molecular weight hydrophilic polymer, at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, and at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the reaction mixture absent the diluent,

Placing the reaction mixture in a mold,

Curing the reaction mixture to form the ophthalmic device, and

Releasing the ophthalmic device from the mold.

40. A composition comprising

monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane;

N,N-dimethylacrylamide;

2-hydroxyethyl methacrylate;

tetraethyleneglycol dimethacrylate;

poly(N-vinyl pyrrolidone) (K value

     90);

bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide; and

3,7-dimethyl-3-octanol.

41. A composition comprising:

monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane;

N,N-dimethylacrylamide;

2-hydroxyethyl methacrylate;

ethylene glycol dimethacrylate;

2-(2′

-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole;

poly(N-vinyl pyrrolidone) (K value

     90);

bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide; and

t-amyl alcohol.