Lubricious coating for medical devices

• US 20040151930A1
• Filed: 11/10/2003
• Published: 08/05/2004
• Est. Priority Date: 12/19/2002
• Status: Active Grant

• Current Assignee: O&M Halyard, Inc. (Owens and Minor Incorporated)
• Original Assignee: Kimberly-Clark Worldwide Incorporated (Kimberly-Clark Corporation)
• Inventors: Perrault, James, Rouns, Cameron
• Granted Patent: US 7,264,859 B2
• Time in Patent Office: Days
• US Class Current: 428/500
• CPC Class Codes: A61L 2400/10 Materials for lubricating medical devices
• CPC Class Codes: A61L 2420/02 Methods for coating medical devices
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/44 having a macromolecular matrix
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: A61L 29/041 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 29/126 having a macromolecular matrix
• CPC Class Codes: A61L 29/14 Materials characterised by their function or physical properties , e.g. lubricating compositions
• CPC Class Codes: A61L 29/145 Hydrogels or hydrocolloids
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/125 having a macromolecular matrix
• CPC Class Codes: A61L 31/14 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: Y10T 428/1393 Multilayer [continuous layer]
• CPC Class Codes: Y10T 428/31576 Ester monomer type [polyvinylacetate, etc.]
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31928 Ester, halide or nitrile of addition polymer
• CPC Class Codes: Y10T 428/31935 Ester, halide or nitrile of addition polymer

Abstract

Medical devices having at least a portion thereof coated with a lubricious polymer are disclosed. The lubricious polymer can be, for instance, a hydrogel polymer, such as a quaternary amine acrylate polymer. To bond the lubricious polymer to the surface of the medical device, the medical device is first subjected to a solvent and a multi-functional monomer. The solvent causes the multi-functional monomer to become imbibed into the surface of the medical device. Thereafter, a polymer having lubricious properties is polymerized on the surface of the device. The multi-functional monomer reacts with the polymer coating securely affixing the polymer coating to the device.

Claims

1. A process for applying a lubricious coating to a surface of a medical device comprising:

providing a medical device made from a polymer;

contacting a surface of the medical device with a solvent and a multi-functional monomer, the solvent causing the multi-functional monomer to be imbibed into the surface of the medical device, the multi-functional monomer comprising an acrylate or an ammonium compound;

drying the surface of the medical device; and

providing and polymerizing a polymer on the surface of the medical device, the polymer reacting with the multi-functional monomer imbibed into the surface of the device to form a lubricious coating.

2. A process as defined in claim 1, wherein the polymer polymerizing on the surface of the medical device and reacting with the multi-functional monomer is a hydrogel polymer.

3. A process as defined in claim 2, wherein the surface of the medical device is made from a thermoplastic or a thermoset polymer.

4. A process as defined in claim 2, wherein the surface of the medical device is made from polyvinyl chloride.

5. A process as defined in claim 2, wherein the solvent causes the surface of the medical device to swell and/or partially dissolve.

6. A process as defined in claim 2, wherein the solvent comprises dimethyl sulphoxide, acetone, methylethyl ketone, toluene, alcohol, or xylene.

7. A process as defined in claim 2, wherein the surface of the medical device is further contacted with an initiator.

8. A process as defined in claim 7, wherein the initiator comprises 1-hydroxycyclohexyl phenyl ketone, α

-hydroxy-1, α

dimethylacetophenone, benzoyl peroxide, azo-bis-isobutyro-nitrile, di-t-butyl peroxide, bromyl peroxide, cumyl peroxide, lauroyl peroxide, isopropyl precarbonate, methylethyl ketone peroxide, cyclohexane peroxide, t-butylhydroperoxide, di-t-amyl peroxide, dicumyl peroxide, t-butyl perbenzoate, a benzoin alkyl ether, a benzophenone, a acetophenone, a thioxanthone, benzyl 2-ethyl anthraquinone, methylbenzoyl formate, 2-hydroxy-2-methyl-1-phenyl propane-1-one, 2-hydroxy-4′

-isopropyl-2-methyl propiophenone, e-hydroxy ketone, tet-remethyl thiuram monosulfide, an allyl diazonium salt, camphorquinone or 4-(N,N-dimethylamino)benzoate.

9. A process as defined in claim 2, wherein the multi-functional monomer and solvent are combined into a solution when contacting the surface of the medical device and wherein the multi-functional monomer cross-links the hydrogel polymer.

10. A process as defined in claim 2, wherein the hydrogel polymer comprises:

11. A process as defined in claim 2, wherein the hydrogel polymer is polymerized by:

contacting the surface of the medical device with a monomer comprising;

 

wherein R′

, R″ and

R′

″

are independently selected from the group consisting of H,C₁ to C¹⁶ alkyl, aryl, arylamine, alkylamine, alkaryl and aralkyl;

X is selected from the group consisting of O and NH;

Y⁻

is an acceptable anionic counterion to the N⁺ of the quaternary amine;

m is an integer greater than 50,000;

and thereafter initiating polymerization.

12. A process as defined in claim 11, whereas polymerization is initiated by exposing the surface of the medical device with ultraviolet light.

13. A process as defined in claim 2, whereas a medical device is a tracheal suction device, a catheter, a guidewire, a stylet, an introducer, an enternal feeding device, or an endotracheal tube.

14. A process as defined in claim 2, wherein the surface of the medical device comprises a silicone or a urethane.

15. A process as defined in claim 2, wherein the hydrogel polymer is made from a monomer comprising an acryloyloxyalkyl-trialkyl-substituted ammonium salt, an acryloyloxyalkyl-aryl-substituted ammonium salt, an acrylamidioalkyl-trialkyl-substituted ammonium salt, or an acrylamidioalkyl-aryl-substituted ammonium salt.

16. A process as defined in claim 2, wherein the hydrogel polymer is made from a monomer comprising acryloyloxyethyltrimethyl ammonium chloride, or acryloyloxyethyltrimethyl ammonium methyl sulfate.

17. A process as defined in claim 2, wherein the multi-functional monomer comprises an alkoxylated acrylate.

18. A process as defined in claim 2, wherein the multi-functional monomer comprises a triacrylate.

19. A process as defined in claim 2, wherein the multi-functional monomer comprises a tetraacrylate, a pentaacrylate, a hexaacrylate, or a diacrylate.

20. A process as defined in claim 2, wherein the multi-functional monomer comprises an ethoxylated trimethylolpropane triacrylate, a propoxylated glyceryl triacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, a propoxylated glyceryl triacrylate, a propoxylated trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tris(2-hydroxy ethyl)isocyanurate triacrylate, di-trimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, an ethoxylated pentaerythritol tetraacrylate, a dipentaerythritol pentaacrylate, a pentaacrylate ester, pentaerythritol tetraacrylate, or a caprolactone modified dipentaerythritol hexaacrylate.

21. A process as defined in claim 2, wherein the multi-functional monomer comprises N,N-Dimethylanimoethyl acrylate dimethylsulfate, N,N-Dimethylaminoethyl acrylate methylchloride, N,N-Dimethylaminoethyl methacrylate dimethylsulfate, N,N-Dimethylaminoethyl methacrylate methylchloride, Diallyldimethylammonium chloride, acryloxyethyldimethyl benzyl ammonium chloride, acryloxyethyltrimethyl ammonium chloride, methacryloxyethyldimethyl benzyl ammonium chloride, or methacryloxyethyltrimethyl ammonium chloride.

22. A process as defined in claim 2, wherein the multi-functional monomer comprises an ethoxylated trimethylolpropane triacrylate.

23. A medical device comprising:

a surface configured to move in relation to an adjacent surface; and

a lubricious coating applied to the surface, the lubricious coating comprising a quaternary amine acrylate polymer that has been cross-linked by a multi-functional monomer, the multi-functional monomer having been imbibed into the surface of the medical device, the multi-functional monomer comprising an acrylate or an ammonium compound.

24. A medical device as defined in claim 23, wherein the surface of the device is made from a thermoplastic or a thermoset.

25. A medical device as defined in claim 23, wherein the surface of the device is made from polyvinyl chloride.

26. A medical device as defined in claim 23, wherein the quaternary amine acrylate polymer comprises:

27. A medical device as defined in claim 23, wherein the medical device comprises tracheal suction device, a catheter, a guidewire, a stylet, an enteral feeding device, an introducer, or an endotracheal tube.

28. A medical device as defined in claim 23, wherein the surface of the device is made from a silicone or a urethane.

29. A medical device as defined in claim 23, wherein the quaternary amine acrylate polymer comprises acryloyloxyalkyl-trialkyl-substituted ammonium salt, an acryloyloxyalkyl-aryl-substituted ammonium salt, an acrylamidoalkyl-trialkyl-substituted ammonium salt, or an acrylamidoalkyl-aryl-substituted ammonium salt.

30. A medical device as defined in claim 23, wherein the quaternary amine acrylate polymer comprises acryloyloxyethyltrimethyl ammonium chloride, or acryloyloxyethyltrimethyl ammonium methyl sulfate.

31. A medical device as defined in claim 23 wherein the multi-functional monomer comprises an alkoxylated acrylate.

32. A medical device as defined in claim 23 wherein the multi-functional monomer comprises a triacrylate.

33. A medical device as defined in claim 23, wherein the multi-functional monomer comprises a tetraacrylate, a pentaacrylate, a hexaacrylate, or a diacrylate.

34. A medical device as defined in claim 23, wherein the multi-functional monomer comprises an ethoxylated trimethylolpropane triacrylate, a propoxylated glyceryl triacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, a propoxylated glyceryl triacrylate, a propoxylated trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tris(2-hydroxy ethyl)isocyanurate triacrylate, di-trimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, an ethoxylated pentaerythritol tetraacrylate, a dipentaerythritol pentaacrylate, a pentaacrylate ester, pentaerythritol tetraacrylate, or a caprolactone modified dipentaerythritol hexaacrylate.

35. A medical device as defined in claim 23, wherein the multi-functional monomer comprises N,N-Dimethylanimoethyl acrylate dimethylsulfate, N,N-Dimethylaminoethyl acrylate methylchloride, N,N-Dimethylaminoethyl methacrylate dimethylsulfate, N,N-Dimethylaminoethyl methacrylate methylchloride, Diallyldimethylammonium chloride, acryloxyethyldimethyl benzyl ammonium chloride, acryloxyethyltrimethyl ammonium chloride, methacryloxyethyldimethyl benzyl ammonium chloride, or methacryloxyethyltrimethyl ammonium chloride.

36. A medical device as defined in claim 23, wherein the multi-functional monomer comprises an ethoxylated trimethylolpropane triacrylate.

37. A process for applying a lubricious coating to the surface of a medical device comprising:

providing a medical device having a surface comprising polyvinyl chloride;

contacting the surface of the medical device with a solvent, an initiator, and a multi-functional monomer, the solvent causing the multi-functional monomer to be imbibed into the surface of the medical device, the multi-functional monomer comprising an ammonium compound;

drying the surface of the medical device;

thereafter contacting the surface of the medical device with a monomer comprising;

 

wherein R′

, R″ and

R′

″

are independently selected from the group consisting of H,C₁ to C₁₆ alkyl, aryl, arylamine, alkylamine, alkaryl and aralkyl;

X is selected from the group consisting of O and NH;

Y⁻

is an acceptable anionic counterion to the N⁺ of the quaternary amine;

m is an integer greater than 50,000;

 

thereafter initiating polymerization;

polymerizing the monomer by exposing the monomer to ultraviolet light, the monomer polymerizing and forming a lubricious coating attached to the medical device.

38. A process as defined in claim 37, wherein the solvent causes the surface of the medical device to swell.

39. A process as defined in claim 37, wherein the solvent causes the surface of the medical device to partially dissolve.

40. A process as defined in claim 37, wherein the solvent comprises dimethyl sulphoxide, acetone, methylethyl ketone, toluene, alcohol, or xylene.

41. A process as defined in claim 37, whereas a medical device is a tracheal suction device, a catheter, a guidewire, a stylet, an introducer, an enteral feeding device, or an endotracheal tube.

42. A process as defined in claim 37, wherein the hydrogel polymer is made from a monomer comprising an acryloyloxyalkyl-trialkyl-substituted ammonium salt, an acryloyloxyalkyl-aryl-substituted ammonium salt, an acrylamidioalkyl-trialkyl-substituted ammonium salt, or an acrylamidoalkyl-aryl-substituted ammonium salt.

43. A process as defined in claim 37, wherein the hydrogel polymer is made from a monomer comprising acryloyloxyethyltrimethyl ammonium chloride, or acryloyloxyethyltrimethyl ammonium methyl sulfate.

44. A process as defined in claim 37, wherein the multi-functional monomer forms a mechanical bond with the surface of the medical device during the process.

45. A process as defined in claim 37, wherein the multi-functional monomer comprises an alkoxylated acrylate.

46. A process as defined in claim 37, wherein the multi-functional monomer comprises a triacrylate.

47. A process as defined in claim 37, wherein the multi-functional monomer comprises a tetraacrylate, a pentaacrylate, a hexaacrylate, or a diacrylate.

48. A process as defined in claim 37, wherein the multi-functional monomer comprises an ethoxylated trimethylolpropane triacrylate, a propoxylated glyceryl triacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, a propoxylated glyceryl triacrylate, a propoxylated trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tris(2-hydroxy ethyl)isocyanurate triacrylate, di-trimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, an ethoxylated pentaerythritol tetraacrylate, a dipentaerythritol pentaacrylate, a pentaacrylate ester, pentaerythritol tetraacrylate, or a caprolactone modified dipentaerythritol hexaacrylate.

49. A process as defined in claim 37, wherein the multi-functional monomer comprises N,N-Dimethylanimoethyl acrylate dimethylsulfate, N,N-Dimethylaminoethyl acrylate methylchloride, N,N-Dimethylaminoethyl methacrylate dimethylsulfate, N,N-Dimethylaminoethyl methacrylate methylchloride, Diallyldimethylammonium chloride, acryloxyethyldimethyl benzyl ammonium chloride, acryloxyethyltrimethyl ammonium chloride, methacryloxyethyldimethyl benzyl ammonium chloride, or methacryloxyethyltrimethyl ammonium chloride.

50. A process a defined in claim 37, wherein the multi-functional monomer comprises an ethoxylated trimethylolpropane triacrylate.