Biomedical devices containing internal wetting agents

• US 7,666,921 B2
• Filed: 09/10/2004
• Issued: 02/23/2010
• Est. Priority Date: 09/10/2001
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Ford, James D., McCabe, Kevin P., Steffen, Robert B., Molock, Frank F., Hill, Gregory A., Vanderlaan, Douglas G., Alli, Azaam
• Primary Examiner(s): Seidleck; James
• Assistant Examiner(s): Figueroa; John J
• Application Number:
  US10/938,361
• Publication Number:
  US 20050154080A1
• Time in Patent Office: 1,992 Days
• Field of Search: None
• US Class Current: 523/107
• 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: C08F 251/00 Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
• CPC Class Codes: C08F 265/04 on to polymers of esters
• CPC Class Codes: C08F 271/00 Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
• CPC Class Codes: C08F 271/02 on to polymers of monomers containing heterocyclic nitrogen
• CPC Class Codes: C08F 283/06 on to polyethers, polyoxymethylenes or polyacetals C08F283/004 takes precedence
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/022 Ophthalmic lenses having special refractive features achieved by special materials or material structures G02C7/049 takes precedence

Abstract

This invention includes a wettable biomedical device containing a high molecular weight hydrophilic polymer and a hydroxyl-functionalized silicone-containing monomer.

Claims

1. A silicone hydrogel comprising the reaction product of about 28 weight % 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, about 31 weight % monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane about 24 weight % N,N-dimethylacrylamide, about 6 weight % 2-hydroxyethyl methacrylate, about 1.5 weight % tetraethyleneglycoldimethacrylate, about 7 weight % polyvinylpyrrolidone, and up to about 1 weight % photoinitiator all based upon weight of all reactive components.

4. The silicone hydrogel of any of claims 1-3 wherein said polyvinylpyrrolidone has a weight average molecular weight of at least about 100,000 daltons.

5. An ophthalmic device comprising the silicone hydrogel of claims 1-3.

6. The ophthalmic 1 device of claim 5 further comprising an advancing dynamic contact angle of less than about 70°

.

7. The ophthalmic 1 device of claim 5 further comprising an advancing dynamic contact angle of less than about 60°

.

8. The ophthalmic device of claim 5 further comprising, after about one day of wear, a tear film break up time of at least about 7 seconds and an oxygen permeability of at least about 50 barriers.

9. The ophthalmic device of claim 6 further comprising a modulus of less than about 90 psi.

10. The ophthalmic device of claim 6 further comprising a water content between about 10 and about 60%.

11. The ophthalmic device of claim 6 further comprising a water content between about 20 and about 55%.

12. The ophthalmic device of claims 6 further comprising a water content between about 25 and about 40%.

13. The ophthalmic device of claim 8 wherein said tear film breakup time is at least about 7 seconds after about 7 days of wear.

2. A silicone hydrogel comprising the reaction product of about 30 weight % 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, about 23 weight % monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane about 31 weight % N,N-dimethylacrylamide, about 7.5 weight % 2-hydroxyethyl methacrylate, about 0.75 weight % ethyleneglycoldimethacrylate, about 6 weight % polyvinylpyrrolidone, and up to about 1 weight % photoinitiator all based upon weight of all reactive components.

3. A silicone hydrogel comprising the reaction product of about 30 weight % 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, about 18 weight % monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane about 31 weight % N,N-dimethylacrylamide, about 9 weight % 2-hydroxyethyl methacrylate, about 0.8 weight % ethyleneglycoldimethacrylate, about 6 weight % polyvinylpyrrolidone, and less than about 1 weight % photoinitiator all based upon weight of all reactive components.