Coating methods

• US 10,328,458 B2
• Filed: 02/28/2013
• Issued: 06/25/2019
• Est. Priority Date: 02/28/2012
• Status: Active Grant

• Current Assignee: Microvention Incorporated (Terumo Corporation)
• Original Assignee: Microvention Incorporated (Terumo Corporation)
• Inventors: Garretson, Joshua, Belletto, John, Cruise, Gregory M.
• Primary Examiner(s): Bowman, Andrew J
• Application Number:
  US13/781,385
• Publication Number:
  US 20130243936A1
• Time in Patent Office: 2,308 Days
• Field of Search: 156 60, 427 23, 427 228, 427301, 427318, 427322, 427534, 427536, 4273935, 4284255, 428334, 623 1, 241 16, 523113
• 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, the method comprising the steps of;

a) mixing a coating composition comprising at a poly(ethylene) glycol, hexamethylene diisocyanate, dichloromethane, dibutyltin dilaurate, and optionally at least one additional compound having at least two isocyanate groups, wherein the coating composition is biocompatible;

b) polymerizing the coating composition to form a polymerized coating composition;

c) creating an active surface on at least two sides of the surface by introducing nucleophilic functional groups onto the surface, wherein the creating step is accomplished using argon or oxygen plasma;

d) forming a coated surface by maintaining the active surface in the polymerized coating composition for at least about 90 seconds, wherein the polymerized coating composition is deposited directly onto both sides of the active surface without a primer base coat; and

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

19. The method according to claim 1, wherein the at least one polyol and the hexamethylene diisocyanate or the additional compound having at least two isocyanate groups are in a ratio of about 1,000 to 1, about 500:

1, about 250;

1, about 100;

1, about 50;

1, about 25;

1, about 10;

1, about 5;

1, about 2;

1, about 1;

1, about 1;

2, about 1;

5, about 1;

10, about 1;

25, about 1;

50, about 1;

100, about 1;

250, about 1;

500 or about 1;

1,000, respectively.

8. A method of coating a surface comprising the steps;

maintaining the surface in a coating composition for at least about 90 seconds after the coating composition has polymerized, wherein the coating composition is biocompatible, comprises a polymerized reaction product of poly(ethylene) glycol, hexamethylene diisocyanate, dichloromethane, dibutyltin dilaurate, and optionally at least one additional compound having at least two isocyanate groups, and is deposited directly onto at least two sides of the surface without a primer base coat, and wherein the surface has been treated with argon or oxygen plasma.

9. The method according to claim 8 wherein the surface is polymeric.

10. The method according to claim 8 wherein the surface is metallic.

11. The method according to claim 8 wherein the at least one additional compound having at least two isocyanate groups is selected from 1,4-tetramethylene di-isocyanate, 1,6-hexamethylene di-isocyanate(HDI), trifunctional biuret, isocyanurate derivatives of HDl, p-tetramethylxylene di-isocyanate, trans 1,4-cyclohexylene di-isocyanate, m-xylene di-isocyanate and combinations thereof.

12. The method according to claim 8 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.

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

a) providing an implantable medical device;

b) mixing a coating composition comprising poly(ethylene) glycol, hexamethylene diisocyanate, dichloromethan, dibutyltin dilaurate, and optionally at least one additional compound having at least two isocyanate groups;

c) polymerizing the coating composition to form a polymerized coating composition;

d) creating an active surface by argon or oxygen plasma treating the implantable medical device surface;

e) forming a coated surface by maintaining the active surface in the polymerized coating composition for at least about 90 seconds, wherein the polymerized coating composition is deposited directly onto the active surface without a primer base coat;

f) curing the coated surface; and

g) forming a coated implantable medical device.

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

15. The method according to claim 13 wherein the surface is metallic.

16. The method according to claim 15 further comprising applying an alkyl carbon containing coating to the metallic surface.

17. The method according to claim 13 wherein the at least one additional compound having at least two isocyanate groups is selected from 1,4-tetramethylene di-isocyanate, 1,6-hexamethylene di-isocyanate(HDI), trifunctional biuret, isocyanurate derivatives of HDl, p-tetramethylxylene di-isocyanate, trans 1,4-cyclohexylene di-isocyanate, m-xylene di-isocyanate and combinations thereof.

18. The method according to claim 13 wherein the implantable medical device is selected from catheters, introducer sheaths, stents, embolic pushers, guide wires, overcoils, and combinations thereof.