US 12,230,801 B2
Electrode materials and processes for their preparation
Charlotte Mallet, Montréal (CA); Serge Verreault, Saint-Tite (CA); Josée Pronovost, Trois-Rivières (CA); Sylviane Rochon, Saint-Adélphe (CA); Jean-Christophe Daigle, St-Bruno-de-Montarville (CA); Kamyab Amouzegar, Mont-Royal (CA); and Karim Zaghib, Longueuil (CA)
Assigned to HYDRO-QUÉBEC, Montréal (CA); and MURATA MANUFACTURING CO., LTD., Nagaokakyo (JP)
Appl. No. 17/265,053
Filed by HYDRO-QUÉBEC, Montréal (CA); and MURATA MANUFACTURING CO., LTD., Nagaokakyo (JP)
PCT Filed Aug. 15, 2019, PCT No. PCT/CA2019/051111
§ 371(c)(1), (2) Date Jul. 13, 2021,
PCT Pub. No. WO2020/034036, PCT Pub. Date Feb. 20, 2020.
Claims priority of provisional application 62/764,663, filed on Aug. 15, 2018.
Prior Publication US 2022/0069308 A1, Mar. 3, 2022
Int. Cl. H01M 4/60 (2006.01); H01M 4/04 (2006.01); H01M 4/139 (2010.01); H01M 4/36 (2006.01); H01M 4/66 (2006.01); H01M 10/0525 (2010.01); H01M 10/0565 (2010.01)
CPC H01M 4/60 (2013.01) [H01M 4/0404 (2013.01); H01M 4/139 (2013.01); H01M 4/366 (2013.01); H01M 4/661 (2013.01); H01M 10/0525 (2013.01); H01M 10/0565 (2013.01); H01M 2300/0082 (2013.01); H01M 2300/0085 (2013.01)] 32 Claims
 
1. An electrode material comprising a film of a metallic material as electrochemically active material, and a compound of any one of Formulae I to IV:

OG Complex Work Unit Chemistry
wherein,
R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from a hydrogen atom, a group selected from halogen, optionally halogenated alkyl, cycloalkyl, or aryl, CN, —NO2, —SO2OM2, —OP(O)(OM2)2, —P(O)(OM2)2, or —C(O)OM2, wherein M2 is a cation of an alkali or alkaline earth metal, or a —OC(O)alkyl, —SO2NH2, —SO2NHalkyl, or —SO2N(alkyl)2 group;
R10 is a hydrogen atom or a carbohydrate, wherein the carbohydrate is a natural or synthetic mono or disaccharide, oligo or polysaccharides;
X1 is, independently in each occurrence, selected from O, S, NH, NR9, and PH, wherein R9 is selected from natural or synthetic carbohydrate and an amine protective group; and
i. a, c and e are single bonds, b and d are double bonds, X2 is O, and M1 is H or a cation of an alkali or alkaline earth metal ion forming a salt with X2 wherein the ratio of cation to the rest of the compound of Formula I, II, or III provides electroneutrality; or
ii. a, c and e are double bonds, b and d are single bonds, X2 is O or NOH(oxime), and M1 is absent;
a geometric isomer of a compound of Formula I, II or III, or a tautomer, oxidized form or salt of a compound of Formula IV;
or a carbohydrate complex or conjugate thereof; and
wherein the metallic material is selected from an alkali or alkaline earth metal, and alloys thereof where the alkali or alkaline earth metal is the major component.