Electrode materials and processes for their preparation

Patent metadata

Field	Value
Publication number	US-2022069308-A1
Application number	US-201917265053-A
Country	US
Kind code	A1
Filing date	Aug 15, 2019
Priority date	Aug 15, 2018
Publication date	Mar 3, 2022
Grant date	—

Abstract

Here is described an electrode material comprising an electrochemically active metallic film and an organic compound, e.g. an indigoid compound (indigo blue or a derivative or precursor thereof). Processes for the preparation of the electrode material and electrodes containing the material, as well as to the electrochemical cells and their use are also contemplated.

First claim

1 . An electrode material comprising a film of a metallic material and a compound of any one of Formulae I to IV:

wherein,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently selected from a hydrogen atom, a group selected from halogen (e.g. F, CI or Br), optionally halogenated alkyl, cycloalkyl, or aryl, CN, —NO 2 , —SO 2 OM 2 , —OP(O)(OM 2 ) 2 , —P(O)(OM 2 ) 2 , or —C(O)OM 2 , wherein M 2 is a cation of an alkali or alkaline earth metal, or a —OC(O)alkyl, —SO 2 NH 2 , —SO 2 NHalkyl, or —SO 2 N(alkyl) 2 group;
R 10 is a hydrogen atom or a carbohydrate, wherein the carbohydrate is a natural or synthetic carbohydrate (e.g. mono or disaccharide, oligo and polysaccharides, e.g. β-D-glucose or cellulose);
X 1 is, independently in each occurrence, selected from O, S, NH, NR 9 , and PH, wherein R 9 is selected from natural or synthetic carbohydrate and protective groups, for instance an amine protective group such as trifluoroacetamide, t-butyloxycarbonyl (Boc), benzyloxycarbonyl (Cbz), 9-fluorenylmethyloxycarbonyl (Fmoc), benzyl (Bn), and the like; and
i. a, c and e are single bonds, b and d are double bonds, X 2 is O, and M 1 is H or a cation of an alkali or alkaline earth metal ion forming a salt with X 2 (e.g. M 1 is Li + , Na + , K + , Ca 2+ , or Mg 2+ ) wherein the ratio of cation to the rest of the compound of Formula I provides electroneutrality (e.g. M 1 may be Li + or (Mg 2+ ) 1/2 ); or
ii. a, c and e are double bonds, b and d are single bonds, X 2 is O or NOH (oxime), and M 1 is absent;

a geometric isomer (e.g. cis or trans) of a compound of Formula I, II or Ill, or a tautomer, oxidized form or salt of a compound of Formula IV;
or a carbohydrate (mono or disaccharide, oligo and polysaccharides, e.g. β-D-glucose or cellulose) complex or conjugate thereof.

2 . The electrode material of claim 1 , wherein X 1 is O, S or NH, preferably X 1 is NH.

3 . (canceled)

4 . The electrode material of claim 1 , wherein the compound is of Formula I, or the compound is of Formula II, or the compound is of Formula III.

5 . (canceled)

6 . (canceled)

7 . The electrode material of claim 1 , wherein R 2 and R 6 are the same and selected from halogen (e.g. F), optionally halogenated alkyl, —CN, and —SO 2 OM 2 , e.g. —CN; and/or R 3 and R 2 are the same and selected from halogen (e.g. F), optionally halogenated alkyl, —CN, and —SO 2 OM 2 , e.g. —CN.

8 . (canceled)

9 . The electrode material of claim 1 , wherein each of R 1 to R 8 are each a hydrogen atom.

10 . The electrode material of claim 1 , wherein a, c and e are single bonds, b and d are double bonds, X 2 is O, and M 1 is H or a cation of an alkali or alkaline earth metal ion forming a salt with X 2 , preferably M 1 is a cation of the same metal as the metal of the film of metallic material.

11 . (canceled)

12 . The electrode material of claim 1 , wherein a, c and e are double bonds, b and d are single bonds, X 2 is O, and M 1 is absent.

13 . The electrode material of claim 1 , wherein the compound is of Formula IV, preferably wherein R 2 is selected from halogen (e.g. F), optionally halogenated alkyl, —CN, and —SO 2 OM 2 , e.g. R 2 is —CN, or wherein each of R 1 to R 4 are each a hydrogen atom.

14 . (canceled)

15 . (canceled)

16 . The electrode material of claim 13 , wherein R 10 is a hydrogen atom.

17 . The electrode material of claim 13 , wherein R 10 is a carbohydrate, e.g. β-D-glucose or cellulose.

18 . The electrode material of claim 1 , wherein the compound is selected from:

19 . The electrode material of claim 1 , wherein the compound is selected from indigo blue, indigo carmine, isoindigo, indigopurpurin and indolinedione, preferably indigo blue or leuco-indigo or a M 1 salt thereof.

20 . (canceled)

21 . (canceled)

22 . The electrode material of claim 1 , wherein the metallic film is a film of an alkali or alkaline earth metal.

23 . The electrode material of claim 22 , wherein the metallic film is a film of lithium, lithium alloy (e.g. Li—Na, Li—Mg, Li—Zn, Li—Al, and the like), sodium, sodium alloy, magnesium, or magnesium alloy, preferably a film of lithium or a lithium alloy comprising at least 50%, at least 75%, at least 90%, at least 95%, or at least 99% of lithium by weight.

24 . (canceled)

25 . (canceled)

26 . The electrode material of claim 1 , wherein the metallic film has a thickness between about 5 μm and about 200 μm, or between about 5 μm and about 100 μm, or between about 10 μm and about 50 μm.

27 . The electrode material of claim 1 , wherein said compound is at a concentration of about 2 wt % or less, or about 1 wt % or less, in the electrode material, or between about 0.0001 wt. % and about 1 wt. %, or about 0.001 wt. % and about 0.5 wt. % relative to the electrode material.

28 . (canceled)

29 . A process for producing an electrode material as defined in claim 1 , comprising the steps of:
a) mixing the compound in a solvent to obtain a mixture (e.g. solution), preferably the solvent is an organic aprotic inert solvent; b) applying the mixture obtained in step (a) on a metallic film to form a treated film; and c) removing the solvent.

30 . (canceled)

31 . The process of claim 30 , wherein the solvent is an alkane solvent, an ether solvent, an aromatic solvent, or a combination thereof, preferably an alkane solvent (e.g. hexane).

32 . (canceled)

33 . The process of claim 29 , further comprising a step (d) of washing the film with a washing solvent, preferably the washing solvent being the same as the solvent of step (a).

34 . (canceled)

35 . The process of claim 29 , wherein step (b) is performed by drop-casting, mold casting, dip coating, spin coating, spray coating, printing, slot die coating, doctor blade coating, chemical vapor deposition, physical vapor deposition, and the like.

36 . A process for producing an electrode material as defined in claim 1 , comprising the steps of:
a) mixing the compound in a lubricating agent to obtain a lubricating composition; b) applying the lubricating composition obtained in step (a) on a metallic foil to form a treated foil; and c) extruding and/or laminating (between at least two rolls) the treated foil obtained in step (b).

37 . The process of claim 36 , wherein steps (b) and (c) are carried out simultaneously.

38 . The process of claim 36 , wherein the lubricating agent comprises a polymer.

39 . The process of claim 36 , wherein the lubricating agent comprises a solvent, preferably an organic aprotic inert solvent, for example, an alkane solvent, an ether solvent, an aromatic solvent or a combination thereof, preferably, the solvent is an alkane solvent (e.g. hexane) and/or an aromatic solvent (e.

Assignees

• Hydro Quebec
• Murata Manufacturing Co

Inventors

• Mallet Charlotte
• Verreault Serge
• Pronovost Josée
• Rochon Sylviane
• Daigle Jean-Christophe
• Amouzegar Kamyab
• Zaghib Karim

Classifications

• Y02E60/10

  Energy storage using batteries · CPC title

• H01M4/134

  Electrodes based on metals, Si or alloys · CPC title

• H01M4/46

  Alloys based on magnesium or aluminium · CPC title

• H01M4/381

  Alkaline or alkaline earth metals elements (H01M4/40 takes precedence) · CPC title

• H01M4/0404

  by coating on electrode collectors · CPC title