Polymers based on ionic monomers, compositions comprising same, methods for manufacturing same, and use thereof in electrochemical applications

Patent metadata

Field	Value
Publication number	US-2023323029-A1
Application number	US-202117758365-A
Country	US
Kind code	A1
Filing date	Jan 22, 2021
Priority date	Jan 24, 2020
Publication date	Oct 12, 2023
Grant date	—

Abstract

The present technology relates to an ionic polymer comprising at least one repeating unit comprising the reaction product between at least one compound comprising at least two functional groups and a metal bis(halosulfonyl)imide for use in electrochemical applications, particularly in electrochemical accumulators such as batteries, electrochromic devices and supercapacitors. The present technology also relates to a polymer composition, a solid polymer electrolyte composition, a solid polymer electrolyte, an electrode material comprising said ionic polymer. Their uses in electrochemical cells and electrochemical accumulators as well as their manufacturing processes are also described.

First claim

What is claimed is:

1 . An ionic polymer comprising at least one repeating unit comprising the reaction product between at least one compound of Formula 1 comprising at least two functional groups and a metal bis(halosulfonyl)imide of Formula 2:

wherein,
A is a substituted or unsubstituted organic group selected from a linear or branched C 1 -C 10 alkylene, a linear or branched C 1 -C 10 alkyleneoxyC 1 -C 10 alkylene, a linear or branched poly(C 1 -C 10 alkyleneoxy)C 1 -C 10 alkylene, a linear or branched polyether and a linear or branched polyester;
X 1 and X 2 are functional groups independently and at each occurrence selected from a hydroxyl group, a thiol group and an amine group;
X 3 and X 4 are halogen atoms each independently selected from F, Cl, Br and I, X 3 and X 4 are both chlorine atoms; and
M n+ is an alkali or alkaline earth metal ion selected from the group consisting of Na + , K + , Li + , Ca 2+ and Mg 2+ ions, preferably M n+ is an alkali metal ion selected from the group consisting of Na + , K + and Li + ions, and more preferably M n+ is Li + .

2 - 5 . (canceled)

6 . The ionic polymer according to claim 1 , wherein:
(i) X 1 and X 2 are both hydroxyl groups and the compound of Formula 1 is preferably selected from glycerol, alkane diols, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,2-propanediol, 1,2-butanediol, 2,3-butanediol, 1,3-butanediol, 1,2-pentanediol, etohexadiol, p-menthane-3,8-diol, 2-methyl-2,4-pentanediol, polycaprolactone diol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, polyethylene glycol, 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol, and a combination of at least two thereof, preferably the compound of Formula 1 is a glycol or glycerol; or (ii) the compound of Formula 1 is selected from alkane diamines, 1,3-propanediamine, 1,4-butanediamine, 1,5-pentanediamine, 1,6-hexanediamine, 1,8-octanediamine, 1,2-propanediamine, 1,2-butanediamine, 2,3-butanediamine, 1,3-butanediamine, 1,2-pentanediamine, 2,4-diamino-2-methylpentane, ethylenediamine, 1,8-diamino-3,6-dioxaoctane, 1,11-diamino-3,6,9-trioxaundecane, 4,9-dioxa-1,12-dodecanediamine, 1,14-diamino-3,6,9,12-tetraoxatetradecane, poly(ethylene glycol) diamine, D, ED or EDR series products commercialized under the brand JEFFAMINE®, and a combination of at least two thereof, preferably the compound of Formula 1 is a JEFFAMINE® D series product selected from JEFFAMINE® ED-600, ED-900 and ED-2003 or is a poly(ethylene glycol) diamine of formula H 2 NCH 2 CH 2 (OCH 2 CH 2 ) n NH 2 , where n is 1 or 2.

7 - 11 . (canceled)

12 . The ionic polymer according to claim 1 , wherein A is:
(i) an optionally substituted linear or branched C 1 -C 10 alkylene and the compound of Formula 1 is a compound of Formula 3:

(ii) a linear or branched and optionally substituted poly(C 1 -C 10 alkyleneoxy)C 1 -C 10 alkylene and the compound of Formula 1 is a compound of Formula 4:

(iii) a linear or branched and optionally substituted polyether and the compound of Formula 1 is a compound of Formula 5:

(iv) an optionally substituted aliphatic polyester, such as polycaprolactone, and the compound of Formula 1 is a compound of Formula 7:

wherein,
X 1 and X 2 are as defined in claim 1 ;
R 1 and R 2 are independently and at each occurrence selected from a hydrogen atom, a hydroxyl group, a thiol group, an amine group, a halogen atom selected from F, Cl, Br and I, and linear or branched substituents selected from C 1 -C 10 alkyl, C 1 -C 10 alkyl-acrylate, C 1 -C 10 alkyl-methacrylate, oxycarbonyl-C 1 -C 10 alkyl-methacrylate, oxycarbonyl-C 1 -C 10 alkyl-acrylate, aminocarbonyl-C 1 -C 10 alkyl-methacrylate, aminocarbonyl-C 1 -C 10 alkyl-acrylate, oxycarbonylamino-C 1 -C 10 alkyl-methacrylate, and oxycarbonylamino-C 1 -C 10 alkyl-acrylate, preferably R 1 and R 2 are independently and at each occurrence selected from a hydrogen atom, a hydroxyl group, a thiol group, an amine group, a fluorine atom and a linear or branched substituent selected C 1 -C 10 alkyl, C 1 -C 10 alkyl-acrylate, C 1 -C 10 alkyl-methacrylate, oxycarbonylamino-C 1 -C 10 alkyl-methacrylate and oxycarbonylamino-C 1 -C 10 alkyl-acrylate;
R 3 , R 4 and R 5 are independently and at each occurrence selected from C 1 -C 10 alkyl groups, preferably R 3 , R 4 and R 5 are methyl groups;
l is a number in the range of 1 to 10;
m is a number in the range of 1 to 68, preferably m is a number in the range of 1 to 10;
n, o and p are selected such that the number average molecular weight of the polyether is between about 220 g/mol and about 2,000 g/mol, upper and lower limits included;
n and p are selected such that the sum (n+p) is comprised within the range of about 1 to about 6;
o is a number in the range of about 2 to about 39;
t and u are numbers in the range of 1 to 10; and
when the compound is of Formulae 3 or 4, X 1 and X 2 are preferably both hydroxyl groups; and
when the compound is of Formula 5, X 1 and X 2 are preferably both amine groups.

13 - 21 . (canceled)

22 . The ionic polymer according to claim 1 , the ionic polymer comprising at least one repeating unit of Formula 8 (a) or is a polymer of Formula 8 (b):

wherein,
A is a substituted or unsubstituted organic group independently and at each occurrence selected from a linear or branched C 1 -C 10 alkylene, a linear or branched C 1 -C 10 alkyleneoxyC 1 -C 10 alkylene, a linear or branched poly(C 1 -C 10 alkyleneoxy)C 1 -C 10 alkylene, a linear or branched polyether and a linear or branched polyester;
X 5 and X 6 are each independently selected from an oxygen atom, a sulfur atom and an —NH group, preferably X 5 and X 6 are both oxygen atoms, both sulfur atoms, or both NH groups;
R 6 is selected from a hydroxyl group, a thiol group, an amine group and a R 7 —X 5 -A-X 6 — group;
R 7 is a crosslinkable group independently at each occurrence selected from acrylate, methacrylate, C 1 -C 10 alkyl-acrylate, C 1 -C 10 alkyl-methacrylate, carbonyl-C 1 -C 10 alkyl-methacrylate carbonyl-C 1 -C 10 alkyl-acrylate, carbonyloxy-C 1 -C 10 alkyl-methacrylate, carbonyloxy-C 1 -C 10 alkyl-acrylate, carbonylamino-C 1 -C 10 alkyl-methacrylate and carbonylamino-C 1 -C 10 alkyl-acrylate;
M n+ is an alkali or alkaline earth metal ion selected from the group consisting of Na + , K + , Li + , Ca 2+ and Mg 2+ ions, preferably M n+ is an alkali metal ion selected from the group consisting of Na + , K + and Li + ions, and more preferably M n+ is Li + ; and
v is a number selected such that the number average molecular weight of the ionic polymer is between about 8,000 g/mol and about 150,000 g/mol, and preferably between about 8,000 g/mol and about 60,000 g/mol, upper and lower limits included.

23 - 28 . (canceled)

29 . The ionic polymer according to claim 1 , the ionic polymer comprising at least one repeating unit selected from the repeating unit of Formulae 9 to 12:

Assignees

• Hydro Quebec

Inventors

• Daigle Jean-Christophe
• Larouche Annie-Pier
• Charest Patrick
• Guerfi Abdelbast
• Dontigny Martin
• Armand Michel
• Zaghib Karim
• Hintennach Andreas

Classifications

• C08G65/34 Primary

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• H01M4/622

  being polymers · CPC title

• H01M4/625

  Carbon or graphite · CPC title

• H01M4/366

  as layered products · CPC title

• H01M4/583

  Carbonaceous material, e.g. graphite-intercalation compounds or CFx · CPC title