Biomedical devices

• US 8,083,348 B2
• Filed: 06/16/2009
• Issued: 12/27/2011
• Est. Priority Date: 06/16/2009
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Linhardt, Jeffrey G., Kunzler, Jay F., Shipp, Devon A.
• Primary Examiner(s): Wu, David W
• Assistant Examiner(s): Nguyen, Vu A
• Application Number:
  US12/456,420
• Publication Number:
  US 20100317816A1
• Time in Patent Office: 924 Days
• Field of Search: 526/286, 351/159, 351/160.R, 351/160.H
• US Class Current: 351/160.H
• CPC Class Codes: C08F 118/02 Esters of monocarboxylic acids
• CPC Class Codes: C08F 20/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 226/02 by a single or double bond to nitrogen
• CPC Class Codes: C08F 26/08 N-Vinyl-pyrrolidine
• CPC Class Codes: C08L 81/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/10 Block- or graft-copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Biomedical devices such as contact lenses formed from a polymerization product of a mixture comprising an ethylenically unsaturated-containing non-amphiphilic macromonomer comprising hydrophilic units or hydrophobic units derived from a living radical polymerization of one or more ethylenically unsaturated hydrophilic monomers or one or more ethylenically unsaturated hydrophobic monomers are disclosed.

Claims

1. A biomedical device which is a polymerization product of a mixture comprising an ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent and a biomedical device-forming comonomer.

2. The biomedical device of claim 1, wherein the ethylenically unsaturated moiety of the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent is selected from the group consisting of (meth)acrylate, (meth)acrylamide, styrenyl, alkenyl, vinyl carbonate, vinyl carbamate groups and combinations thereof.

3. The biomedical device of claim 1, wherein the ethylenically unsaturated moiety of the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent is represented by the general formula:

4. The biomedical device of claim 1, wherein the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent comprises hydrophilic units derived from a hydrophilic monomer selected from the group consisting of an unsaturated carboxylic acid, acrylamide, vinyl lactam, ethylenically unsaturated poly(alkylene oxide), (meth)acrylic acid, hydroxyl-containing-(meth)acrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomer, and mixtures thereof.

5. The biomedical device of claim 1, wherein the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent comprises hydrophilic units derived from a hydrophilic monomer selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, N-vinyl caprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate and mixtures thereof.

6. The biomedical device of claim 1, wherein the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent comprises hydrophilic units derived from an ethylenically unsaturated polymerizable alkoxylated polymer selected from the group consisting of polyethylene glycol (PEG)-200 methacrylate, PEG-400 methacrylate, PEG-600 methacrylate, PEG-1000 methacrylate and mixtures thereof.

7. The biomedical device of claim 1, wherein the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent comprises at least two of the same or different hydrophilic units.

8. The biomedical device of claim 7, wherein the hydrophilic units comprises one or more of polyoxyalkylenes, polyacrylamides, polyvinylpyrrolidones, polyvinyl alcohols, and poly(hydroxyethyl methacrylate).

9. The biomedical device of claim 1, wherein the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent comprises hydrophobic units derived from a hydrophobic monomer selected from the groups consisting of an ethylenically unsaturated polymerizable fluorine-containing monomer, ethylenically unsaturated polymerizable fatty acid ester-containing monomer, ethylenically unsaturated polymerizable polysiloxanylalkyl-containing monomer, ethylenically unsaturated polymerizable monomer having ring-opening reactive functionalities, and mixtures thereof.

10. The biomedical device of claim 1, wherein the ethylenically unsaturated-containing non-amphiphilic macromonomer reversible addition fragmentation chain transfer agent comprises hydrophobic units derived from a hydrophobic monomer selected from the group consisting of alkyl (meth)acrylates, N-alkyl (meth)acrylamides, alkyl vinylcarbonates, alkyl vinylcarbamates, fluoroalkyl (meth)acrylates, N-fluoroalkyl (meth)acrylamides, N-fluoroalkyl vinylcarbonates, N-fluoroalkyl vinylcarbamates, silicone-containing (meth)acrylates, (meth)acrylamides, vinyl carbonates, vinyl carbamates, vinyl esters, styrenic monomers, polyoxypropylene (meth)acrylates and mixtures thereof.

11. The biomedical device of claim 1, wherein the reversible addition fragmentation chain transfer agent comprises a dithioester group, xanthate group, dithiocarbamate group or trithiocarbonate group.

12. The biomedical device of claim 1, wherein the biomedical device-forming comonomer is a silicone-containing monomer.

13. The biomedical device of claim 1, wherein the biomedical device-forming comonomer is selected from the group consisting of an unsaturated carboxylic acid, acrylamide, vinyl lactam, poly(alkyleneoxy)(meth)acrylate, (meth)acrylic acid, hydroxyl-containing-(meth)acrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomer and mixtures thereof.

14. The biomedical device of claim 1, wherein the biomedical device-forming comonomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, N-vinyl caprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate and mixtures thereof.

15. The biomedical device of claim 1, wherein the device is a contact lens.

16. The biomedical device of claim 15, wherein the contact lens is a rigid gas permeable contact lens.

17. The biomedical device of claim 15, wherein the contact lens is a soft contact lens.

18. The biomedical device of claim 15, wherein the contact lens is a hydrogel contact lens.

19. The biomedical device of claim 1, wherein the device is an intraocular lens.

20. The biomedical device of claim 1, wherein the device is a corneal implant.