Biomedical devices with amid-containing coatings

• US 6,500,481 B1
• Filed: 06/09/1999
• Issued: 12/31/2002
• Est. Priority Date: 06/11/1998
• Status: Expired due to Term

• Current Assignee: Johnson & Johnson Vision Products, Inc.
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Wong Meyers, Ann-Marie, Turner, David C., Vanderlaan, Douglas G., Wood, Joe M.
• Primary Examiner(s): SZEKELY, PETER A
• Application Number:
  US09/328,628
• Time in Patent Office: 1,301 Days
• Field of Search: 427/2.24, 427/164, 427/165, 428/411.1, 351/160.H, 523/106, 523/107, 523/108, 264/1.7
• US Class Current: 427/2.24
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08L 33/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 35/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]

Abstract

The invention provides biomedical devices. In particular, the invention provides biomedical devices on the surfaces of which stable, hydrophilic, amide-containing coatings are formed.

Claims

1. A method for manufacturing biomedical devices comprising the step of contacting at least one surface of a biomedical device, the surface comprising an effective amount of carboxyl groups, with a coating-effective amount of an amine and a coupling effective amount of at least one coupling agent at a temperature of about 0 to about 95°

C. and for a time of about 1 to about 360 minutes to produce a stable, amide-containing coating on the surface.

2. The method of claim 1, wherein the device is a contact lens.

3. The method of claim 1 or 2, wherein the amount of carboxyl groups is about 0.65 to about 65 nMol/cm².

4. The method of claim 1 or 2, wherein the coupling agent is selected from the group consisting of a carbodiimide., acid halide of an inorganic or organic acid, isocyanide, N,N′

-carbonyldiimidazole and combinations thereof.

5. The method of claim 4, wherein the coupling agent is a carbodiimide.

6. The method of claim 5, wherein the carbodiimide is 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide or dicyclohexyl carbodiimide.

7. The method of claim 1 or 2, wherein the amine is selected from the group consisting of a primary amine, a secondary amine, an acid salt of a primary or secondary amine, an amine-containing protein, an amine-containing antibiotic, and combinations thereof.

8. The method of claim 1 or 2, wherein the amine is selected from the group consisting of ammonium chloride, glucosamine hydrochloride, dimethylamine hydrochloride, ethanolamine hydrochloride, diethanolamine hydrochloride, polyethylene glycol amines, lactoferrin, lysozyme, albumin, casein, cytochrome C, immunoglobulins, avidin, heparin, polymyxin, and combinations thereof.

9. The method of claim 1 or 2, wherein the stable, amide-containing coating produced is a polyacrylamide or a polymethacrylamide coating.

10. A method for manufacturing biomedical devices comprising the steps of:

a.) coating at least one surface of a device with one or more carboxyl functional polymers; and

b.) contacting the at least one surface with a coating-effective amount of an amine and a coupling effective amount of at least one coupling agent at a temperature of about 0 to about 95°

C. and for a time of about 1 to about 360 minutes to produce a stable, amide-containing coating on the surface.

11. The method of claim 10, wherein the device is a contact lens.

12. The method of claim 10 or 11 wherein the one or more carboxyl functional polymer is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, , and mixtures thereof.

13. The method of claim 10 or 11, wherein the carboxyl functional polymer is poly(acrylic acid).

14. The method of claim 10 or 11, wherein the coupling agent is selected from the group consisting of a carbodiimide, acid halide of an inorganic or organic acid, isocyanide, and combinations thereof.

15. The method of claim 10 or 11, wherein the coupling agent is a carbodiimide.

16. The method of claim 15, wherein the carbodiimide is 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide or dicyclohexyl carbodiimide.

17. The method of claim 10 or 11, wherein the amine is selected from the group consisting of a primary amine, a secondary amine, an acid salt of a primary or secondary amine, an amine-containing protein, an amine-containing antibiotic, and combinations thereof.

18. The method of claim 10 or 11, wherein the amine is selected from the group consisting of ammonium chloride, glucosamine hydrochloride,dimethylamine hydrochloride, polyethylene glycol amines, lactoferrin, lysozyme, albumin, casein, cytochrome C, immunoglobulins, avidin, heparin, polymyxin, and combinations thereof.

19. The method of claim 10, wherein step a.) is carried out by:

(i.) contacting the at least one surface with a coupling effective amount of a coupling agent for about 0.5 to about 60 minutes; and

(ii.) contacting, subsequently, the at least one surface with a carboxyl functional polymer for a period of about 1 to about 1000 minutes to coat the at least one surface with the carboxyl functional polymer.

20. The method of claim 19, wherein the coupling agent is selected from the group consisting of a carbodiimide, acid halide of an inorganic or organic acid, isocyanide, and combinations thereof.

21. The method of claim 20, wherein the coupling agent is a carbodiimide.

22. The method of claim 21, wherein the carbodiimide is 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide.

23. The method of claim 19, wherein the carboxyl functional polymer is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, carboxymethylated polymers, and mixtures thereof.

24. The method of claim 23, wherein the carboxyl functional polymer is poly(acrylic acid).

25. The method of claim 24, wherein the coupling agent is a carbodiimide.

26. The method of claim 25, wherein the carbodiimide is 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide.

27. The method of claim 24, wherein the amine is selected from the group consisting of a primary amine, a secondary amine, an acid salt of a primary or secondary amine, an amine-containing protein, an amine-containing antibiotic, and combinations thereof.

28. The method of claim 27, wherein the amine is lactoferrin.

29. A contact lens comprising at least one surface having an amide-containing coating coupled thereto by at least one coupling agent.

30. The lens of claim 29, wherein the amide-containing coating is a coating formed from at least one amine selected from the group consisting of ammonium chloride, glucosamine hydrochloride, dimethylamine hydrochloride, ethanolamine hydrochloride, diethanolamine hydrochloride, polyethylene glycol amines, lactoferrin, lysozyme, albumin, casein, cytochrome C, immunoglobulins, avidin, heparin, polymyxin, and combinations thereof.

31. The lens of claim 29, wherein the amide-containing coating is a polyacrylamide coating.