Surface modification of functional group-containing intraocular lenses with catalyst containing reactive polymer system

• US 20040006385A1
• Filed: 06/28/2002
• Published: 01/08/2004
• Est. Priority Date: 06/28/2002
• Status: Active Grant

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: McGee, Joseph A., Salamone, Joseph C., Valint, Paul L. Jr.
• Granted Patent: US 7,270,678 B2
• Time in Patent Office: Days
• US Class Current: 623/5.16
• CPC Class Codes: A61F 2/16 Intraocular lenses
• CPC Class Codes: A61L 2400/18 Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: C08J 2333/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
• CPC Class Codes: C08J 7/12 Chemical modification

Abstract

Surface modified medical devices such as intraocular lens implants formed from one or more functional group-containing materials using reactive, hydrophilic polymers with catalyst functionality for the purpose of reducing or eliminating lens epithelial cell growth thereon, reducing or eliminating silicone oil absorption upon subsequent surgical exposure and/or reducing implantation inserter friction is provided herein. Additionally, a method of making and using surface modified intraocular lens implants is provided.

Claims

1. A surface modified medical device comprising:

a medical device manufactured from a functional group-containing polymeric material; and

one or more reactive, hydrophilic polymers with an additive having catalyst functionality applied to the surface of said medical device;

whereby a chemical reaction between said functional group-containing polymeric material and said one or more reactive, hydrophilic polymers form covalent bonds therebetween.

2. The medical device of claim 1 wherein said medical device is an intraocular lens.

3. The medical device of claim 1 wherein said medical device is a contact lens or corneal inlay.

4. The surface modified medical device of claim 1 wherein said additive having catalyst functionality is selected from the group consisting of N,N-dimethylaminopropyl methacrylamide, 2-(N,N-dimethylamino)ethyl methacrylate, 2-(N,N-dimethylamino)ethyl acrylate, (N,N-dimethyl aminomethyl)styrene, N-[3-(N,N-dimethylamino)propyl]acrylamide and 3-(N,N-dimethylamino)propyl acrylate.

5. The surface modified medical device of claim 1 wherein said functional group-containing polymeric material includes a material selected from the group consisting of 2-hydroxyethyl methacrylate, glyceryl methacrylate, 3-hydroxypropyl methacrylamide, methacrylic acid, acrylic acid, N-carboxy-β

-alanine-N-vinyl ester, 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one, 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, spiro-4′

-(2′

-isopropenyl-2′

-oxazolin-5-one)cyclohexane, spiro-4′

-(2′

-vinyl-2′

-oxazolin-5′

-one)cyclohexane, 2-(1-propenyl)-4,4-dimethyl-oxazolin-5-one, methacrylic anhydride, acrylic anhydride, maleic anhydride and glycidyl methacrylate.

6. The surface modified medical device of claim 1 wherein said functional group-containing polymeric material is selected from the group consisting of silicone polymers, hydrocarbon and fluorocarbon polymers, hydrogels, acrylic polymers, polyesters, polyamides, polyurethanes, silicone polymers with hydrophilic monomer units, fluorine-containing polysiloxane elastomers and combinations thereof.

7. The surface modified medical device of claim 1 wherein said functional group-containing polymeric material is poly(HEMA-co-HOHEXMA.

8. The surface modified medical device of claim 1 wherein said one or more reactive, hydrophilic polymers are produced from hydrophilic monomers selected from the group consisting of aprotic types and protic types.

9. The surface modified medical device of claim 1 wherein said one or more reactive, hydrophilic polymers are produced from hydrophilic monomers selected from the group consisting of N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-methylmethacrylamide and N-methylacrylamide.

10. The surface modified medical device of claim 1 wherein said one or more reactive, hydrophilic polymers are produced from hydrophilic monomers having reactive chemical functionality selected from the group consisting of epoxide functionality, carboxylic acid functionality, anhydride functionality, oxazolinone functionality and alcohol functionality.

11. The surface modified medical device of claim 1 wherein said one or more reactive, hydrophilic polymers is poly(DMA-co-GMA).

23. A method of using the surface modified medical device of claim 1 comprising:

creating an incision in an eye; and

implanting said surface modified medical device through said incision prior to closing said incision.

24. The method of using the surface modified medical device of claim 23 wherein said medical device is an intraocular lens.

25. The method of using the surface modified medical device of claim 23 wherein said medical device is a corneal inlay.

26. The method of using the surface modified medical device of claim 23, 24 or 25 wherein a natural lens is removed from said eye prior to implanting said surface modified medical device within said eye.

27. The method of using the surface modified medical device of claim 23 or 24 wherein a natural lens is removed from said eye prior to implanting said surface modified medical device within a lens capsule of said eye.

28. The method of using the surface modified medical device of claim 23, 24 or 25 wherein a natural lens is removed from said eye prior to implanting said surface modified medical device within said eye using an implantation inserter.

29. The method of using the surface modified medical device of claim 23 or 24 wherein a natural lens is removed from said eye prior to implanting said surface modified medical device within a capsule of said eye using an implantation inserter.

12. A method of making a surface modified medical device comprising:

producing a medical device from a functional group-containing polymeric material; and

exposing one or more reactive, hydrophilic polymers with an additive having catalyst functionality to the surface of said medical device;

whereby a chemical reaction between said functional group-containing polymeric material and said one or more reactive, hydrophilic polymers form covalent bonds therebetween.

13. The method of claim 12 wherein said medical device is an intraocular lens or corneal inlay.

14. The method of claim 12 wherein said medical device is a contact lens.

15. The method of claim 12 wherein said additive having catalyst functionality is selected from the group consisting of 3-(N,N-dimethylamino)propyl methacrylamide, 2-(N,N-dimethylamino)ethyl methacrylate, 2-(N,N-dimethylamino)ethyl acrylate, (N,N-dimethyl aminomethyl)styrene, N-[3-(N,N-dimethylamino)propyl]acrylamide and 3-(N,N-dimethylamino)propyl acrylate.

16. The method of claim 12 wherein said functional group-containing polymeric material includes a material selected from the group consisting of 2-hydroxyethyl methacrylate, glyceryl methacrylate, 3-hydroxypropyl methacrylamide, methacrylic acid, acrylic acid, N-carboxy-β

-alanine-N-vinyl ester, 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one, 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, spiro-4′

-(2′

-isopropenyl-2′

-oxazolin-5-one)cyclohexane, spiro-4′

-(2′

-vinyl-2′

-oxazolin-5′

-one)cyclohexane, 2-(1-propenyl)-4,4-dimethyl-oxazolin-5-one, methacrylic anhydride, acrylic anhydride, maleic anhydride and glycidyl methacrylate.

17. The method of claim 12 wherein said functional group-containing polymeric material is selected from the group consisting of silicone polymers, hydrocarbon and fluorocarbon polymers, hydrogels, acrylic polymers, polyesters, polyamides, polyurethanes, silicone polymers with hydrophilic monomer units, fluorine-containing polysiloxane elastomers and combinations thereof.

18. The method of claim 12 wherein said functional group-containing polymeric material is poly(HEMA-co-HOHEXMA).

19. The method of claim 12 wherein said one or more reactive, hydrophilic polymers are produced from hydrophilic monomers selected from the group consisting of aprotic types and protic types.

20. The method of claim 12 wherein said one or more reactive, hydrophilic polymers are produced from hydrophilic monomers selected from the group consisting of N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-methylmethacrylamide and N-methylacrylamide.

21. The method of claim 12 wherein said one or more reactive, hydrophilic polymers are produced from hydrophilic monomers having reactive chemical functionality selected from the group consisting of epoxide functionality, carboxylic acid functionality, anhydride functionality, oxazolinone functionality and alcohol functionality.

22. The method of claim 12 wherein said one or more reactive, hydrophilic polymers is poly(DMA-co-GMA).