Conductive polymeric coatings, medical devices, coating solutions and methods

Patent metadata

Field	Value
Publication number	US-2016208114-A1
Application number	US-201414914586-A
Country	US
Kind code	A1
Filing date	Aug 25, 2014
Priority date	Aug 25, 2013
Publication date	Jul 21, 2016
Grant date	—

Abstract

The invention includes conductive polymeric coatings, medical device, coating solutions and methods of making the same. A coating solution for forming a conductive polymer layer can include a conductive monomer, at least one photoreactive component comprising an anionic photoreactive cross-linking agent or an anionic photoreactive hydrophilic polymer, and a solvent. A medical device can include an electrode and an electrically conductive coating disposed over the electrode. The electrically conductive coating can include a reaction product of the conductive monomer and the at least one photoreactive component. Other aspects are included herein.

First claim

1 . A coating solution for forming a conductive polymer layer comprising:
a conductive monomer or a conductive polymer; at least one photoreactive component comprising an anionic photoreactive cross-linking agent or an anionic photoreactive hydrophilic polymer; and a solvent.

2 . The coating solution of claim 1 , the conductive monomer comprising acetylene, fluorene, para-phenylene, pyrene, pyrrole, carbazole, indole, phenyl azide, aniline, thiophene, pyridine, or a mixture or functionalized derivative thereof.

3 . The coating solution of claim 1 or 2 , the conductive monomer comprising 3,4-ethylenedioxythiophene (EDOT) or a functionalized, dimerized or trimerized derivative thereof.

4 . The coating solution of claim 3 , the conductive monomer comprising EDOT.

5 . The coating solution of claim 3 , the conductive monomer comprising a functionalized derivative of EDOT selected from the group consisting of hydroxymethyl-EDOT, EDOT-vinyl, EDOT-ether allyl, EDOT-COOH, EDOT-MeOH, EDOT-silane, EDOT-vinyl, EDOT-acrylate, EDOT-sulfonate, EDOT-amine, EDOT-amide, bi-EDOT, tri-EDOT, and combinations thereof.

6 . The coating solution of claim 5 , the conductive monomer comprising a functionalized derivative of EDOT selected from the group consisting of hydroxymethyl-EDOT, EDOT-vinyl, EDOT-ether allyl, EDOT-acrylate, and combinations thereof.

7 . The coating solution of claim 3 , the conductive monomer comprising a functionalized derivative of EDOT comprising an alkene functional group.

8 . The coating solution of any one of claims 1 to 7 , the conductive monomer comprises a mixture of EDOT and a functionalized EDOT derivative.

9 . The coating solution of claim 8 , the functionalized EDOT derivative comprising an alkene functional group.

10 . The coating solution of claim 8 or 9 , the molar ratio of EDOT to the functionalized EDOT derivative is from about 0.5:1 to about 10:1.

11 . The coating solution of claim 10 wherein the molar ratio of EDOT to the functionalized EDOT derivative is from about 0.5:1 to about 2:1.

12 . The coating solution of claim 1 , the conductive monomer comprising a propylenedioxythiophene or a functionalized derivative thereof.

13 . The coating solution of claim 12 , the propylenedioxythiophene comprising 3,4-propylenedioxythiophene (ProDOT), 3,4-(2,2-dimethylpropylenedioxy)thiophene, 3,4-(2′,2′-diethylpropylene)dioxythiophene, or a functionalized derivative thereof.

14 . The coating solution of claim 13 , the conductive monomer comprising ProDOT or a functionalized derivative thereof.

15 . The coating solution of claim 1 , the conductive monomer comprising hexylthiophene or a functionalized derivative thereof.

16 . The coating solution of claim 1 , the conductive monomer comprising 4-vinylpyridine.

17 . The coating solution of claim 1 , the conductive monomer comprising 3-methyl thiophene.

18 . The coating solution of any one of claims 1 - 17 , the amount of the conductive monomer in the coating solution comprising from about 0.001 M to about 1 M.

19 . The coating solution of claim 18 , the amount of the conductive monomer in the coating solution comprising from about 0.001 M to about 0.2 M.

20 . The coating solution of claim 1 , the conductive polymer comprising a polyacetylene, a poly(vinyl alcohol), a poly(fluorene), a polyphenylene, a polyphenylene vinylene, a polypyrene, a polyazulene, a polynaphthalene, a poly(pyrrole), a polycarbazole, a polyindole, a polyazepine, a polyaniline, a polyacene, a polythiophene, a polythiophene vinylene, a poly(p-phenylene sulfide), a polypyridine, or functionalized derivatives, precursors or blends thereof.

21 . The coating solution of claim 1 or 20 , the conductive polymer comprising poly(3,4-ethylenedioxythiophene) (PEDOT) or a functionalized derivative thereof.

22 . The coating solution of claim 21 , the conductive polymer comprising PEDOT.

23 . The coating solution of claim 21 , the conductive polymer being derived from a functionalized derivative of EDOT selected from the group consisting of hydroxymethyl-EDOT, EDOT-vinyl, EDOT-ether allyl, EDOT-COOH, EDOT-MeOH, EDOT-silane, EDOT-vinyl, EDOT-acrylate, EDOT-sulfonate, EDOT-amine, EDOT-amide, and combinations thereof.

24 . The coating solution of claim 23 , the conductive polymer being derived from a functionalized derivative of EDOT selected from the group consisting of hydroxymethyl-EDOT, EDOT-vinyl, EDOT-ether allyl, EDOT-acrylate, and combinations thereof.

25 . The coating solution of claim 20 , the conductive polymer being derived from a functionalized derivative of EDOT comprising an alkene functional group.

26 . The coating solution of any one of claims 1 and 23 - 25 , the conductive polymer being derived from a mixture of EDOT and a functionalized EDOT derivative.

27 . The coating solution of claim 26 , the functionalized EDOT derivative comprising an alkene functional group.

28 . The coating solution of claim 26 or 27 , the molar ratio of EDOT to the functionalized EDOT derivative is from about 0.5:1 to about 10:1.

29 . The coating solution of claim 28 wherein the molar ratio of EDOT to the functionalized EDOT derivative is from about 0.5:1 to about 2:1.

30 . The coating solution of claim 1 , the conductive polymer being derived from a propylenedioxythiophene or a functionalized derivative thereof.

31 . The coating solution of claim 30 , the propylenedioxythiophene comprising ProDOT, 3,4-(2,2-dimethylpropylenedioxy)thiophene, 3,4-(2′,2′-diethylpropylene)dioxythiophene, or a functionalized derivative thereof.

32 . The coating solution of claim 31 , the conductive polymer being derived from ProDOT or a functionalized derivative thereof.

33 . The coating solution of claim 1 , the conductive polymer comprising poly(hexylthiophene) or a functionalized derivative thereof.

34 . The coating solution of claim 1 , the conductive polymer comprising poly-4-vinylpyridine.

35 . The coating solution of claim 1 , the conductive polymer comprising poly(diallyldimethylammonium chloride).

36 . The coating solution of any one of claims 1 and 20 - 35 , the amount of the conductive polymer in the coating solution comprising from about 0.001 M to about 1 M.

37 . The coating solution of claim 36 , the amount of the conductive polymer in the coating solution comprising from about 0.001 M to about 0.2 M.

38 . The coating solution of any one of claims 1 - 37 , further comprising a non-charged photoreactive hydrophilic polymer.

39 . The coating solution of claim 38 , further comprising a non-charged hydrophilic polymer derived from 1-vinyl-2-pyrrolidone (PVP), PVP comprising photoreactive functional groups, N-(3-aminopropyl)methacrylamide (APMA), AMPA comprising photoreactive functional groups, and combinations thereof.

40 . The coating solution of claim 38 or 39 , the anionic photoreactive hydrophilic polymer and the non-charged hydrophilic polymer being present in a weight ratio of from about 1:10 to about 10:1.

41 . The coating solution of claim 40 , the anionic photoreactive hydrophilic polymer and the non-charged hydrophilic polymer b

Assignees

• Hendricks Jeffrey L
• Richardson-Burns Sarah M
• Mallires Kyle
• Spanninga Sarah A
• Surmodics Inc

Inventors

• Hendricks Jeffrey L
• Richardson-Burns Sarah M
• Mallires Kyle
• Spanninga Sarah A
• Lockwood Nathan A
• Hergenrother Robert W
• Jelle Bruce M

Classifications

• A61N1/05

  for implantation or insertion into the body, e.g. heart electrode (A61N1/06 takes precedence) · CPC title

• A61B2018/00136

  with polymer · CPC title

• A61B5/6846

  specially adapted to be brought in contact with an internal body part, i.e. invasive · CPC title

• A61B2018/00071

  Electrical conductivity · CPC title

• A61B18/12

  by passing a current through the tissue to be heated, e.g. high-frequency current · CPC title