COATING METHODS

• US 20130243936A1
• Filed: 02/28/2013
• Published: 09/19/2013
• Est. Priority Date: 02/28/2012
• Status: Active Grant

• Current Assignee: Microvention Incorporated (Terumo Corporation)
• Original Assignee: Microvention Incorporated (Terumo Corporation)
• Inventors: Cruise, Gregory M., Garretson, Joshua, Belletto, John
• Granted Patent: US 10,328,458 B2
• Time in Patent Office: Days
• US Class Current: 427/2.25
• CPC Class Codes: A61L 2420/02 Methods for coating medical devices
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: B05D 2503/00 Polyurethanes
• CPC Class Codes: B05D 3/142 Pretreatment
• CPC Class Codes: B05D 5/00 Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/7831 containing biuret groups
• CPC Class Codes: C09D 171/08 Polyethers derived from hydroxy compounds or from their metallic derivatives C09D171/02 takes precedence
• CPC Class Codes: C09D 175/08 from polyethers

Abstract

Described herein are methods of coating both metallic and polymeric surfaces adding hydrophilicity comprising the steps mixing a coating composition comprising at least one polyol, at least one compound having at least two isocyanate groups, and an organic solvent; introducing nucleophilic functional groups on the surface thereby creating an active surface; subjecting the active surface to the coating composition thereby forming a coated surface; and curing the coated surface. Medical devices, for example, implantable medical devices can be coated by the methods described herein.

Claims

1. A method of coating a surface comprising the steps

a) mixing a coating composition comprising at least one polyol, at least one compound having at least two isocyanate groups, and an organic solvent;

b) introducing nucleophilic functional groups on the surface thereby creating an active surface;

c) subjecting the active surface to the coating composition thereby forming a coated surface; and

d) curing the coated surface.

2. The method according to claim 1 wherein the surface is polymeric.

3. The method according to claim 2 wherein the surface contains alkyl carbons.

4. The method according to claim 1 wherein the surface is metallic.

5. The method according to claim 4 further comprising a step after a) wherein the step comprises applying an alkyl carbon containing coating to the metallic surface.

6. The method according to claim 5 wherein the alkyl carbon containing coating is a silane coating.

7. The methods according to claim 1 wherein the introducing step is accomplished using a plasma gas.

8. The method according to claim 7 wherein the plasma gas is argon.

9. The method according to claim 1 wherein the at least one polyol is selected from poly(ethylene glycol), poly(tetramethylene oxide), ethoxylated trimethylol propane, glycerin, poly(hydroxyethyl methacrylate), poly(vinyl alcohol), and combinations thereof.

10. The method according to claim 1 wherein the at least one compound having at least two isocyanate groups is selected from 1,4-tetramethylene di-isocyanate, 1,6-hexamethylene di-isocyanate(HDI), trifunctional biuret, isocyanurate derivates of HDI, p-tetramethylxylene di-isocyanate, trans 1,4-cyclohexylene di-isocyanate, m-xylene di-isocyanate and combinations thereof.

11. The method according to claim 1 wherein the at least one compound having at least two isocyanate groups is hexamethylene diisocyanate.

12. A method of coating a surface comprising the steps

contacting a coating composition with a surface, wherein the coating composition comprises at least one polyol, at least one compound having at least two isocyanate groups, and an organic solvent with a surface,

and wherein the surface has been treated with a plasma.

13. The method according to claim 12 wherein the surface is polymeric.

14. The method according to claim 12 wherein the surface is metallic.

15. The method according to claim 12 wherein the plasma is argon.

16. The method according to claim 12 wherein the at least one polyol is selected from poly(ethylene glycol), poly(tetramethylene oxide), ethoxylated trimethylol propane, glycerin, poly(hydroxyethyl methacrylate), poly(vinyl alcohol), and combinations thereof.

17. The method according to claim 12 wherein the at least one compound having at least two isocyanate groups is selected from 1,4-tetramethylene di-isocyanate, 1,6-hexamethylene di-isocyanate(HDI), trifunctional biuret, isocyanurate derivates of HDI, p-tetramethylxylene di-isocyanate, trans 1,4-cyclohexylene di-isocyanate, m-xylene di-isocyanate, hexamethylene diisocyanate and combinations thereof.

18. The method according to claim 12 wherein the surface is selected from a catheters surface, an introducer sheath surface, a stent surface, an embolic pusher surface, a guide wire surface, an overcoil surface, and combinations thereof.

19. A method of coating an implantable medical device surface comprising the steps

a) providing an implantable medical device;

b) mixing a coating composition comprising at least one polyol, at least one compound having at least two isocyanate groups, and an organic solvent;

c) plasma treating a surface of the implantable medical device thereby creating an active surface;

d) subjecting the active surface to the coating composition thereby forming a coated surface;

e) curing the coated surface; and

f) forming a coated implantable medical device.

20. The method according to claim 19 wherein the surface is polymeric.

21. The method according to claim 19 wherein the surface is metallic.

22. The method according to claim 19 further comprising applying an alkyl carbon containing coating to the metallic surface.

23. The method according to claim 19 wherein the plasma is argon.

24. The method according to claim 19 wherein the at least one polyol is selected from poly(ethylene glycol), poly(tetramethylene oxide), ethoxylated trimethylol propane, glycerin, poly(hydroxyethyl methacrylate), poly(vinyl alcohol), and combinations thereof.

25. The method according to claim 19 wherein the at least one compound having at least two isocyanate groups is selected from 1,4-tetramethylene di-isocyanate, 1,6-hexamethylene di-isocyanate(HDI), trifunctional biuret, isocyanurate derivates of HDI, p-tetramethylxylene di-isocyanate, trans 1,4-cyclohexylene di-isocyanate, m-xylene di-isocyanate, hexamethylene diisocyanate and combinations thereof.

26. The method according to claim 19 wherein the implantable medical device is selected from catheters, introducer sheaths, stents, embolic pushers, guide wires, overcoils, and combinations thereof.