CA2283670A1 - Materiaux utiles en tant que solutes electrolytiques - Google Patents

Materiaux utiles en tant que solutes electrolytiques Download PDF

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CA2283670A1
CA2283670A1 CA002283670A CA2283670A CA2283670A1 CA 2283670 A1 CA2283670 A1 CA 2283670A1 CA 002283670 A CA002283670 A CA 002283670A CA 2283670 A CA2283670 A CA 2283670A CA 2283670 A1 CA2283670 A1 CA 2283670A1
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Canada
Prior art keywords
compound
oxide
optionally
electrolytic
cation
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CA002283670A
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CA2283670C (fr
Inventor
Christophe Michot
Michel Armand
Michel Gauthier
Nathalie Ravet
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Universite de Montreal
Acep Inc
Centre National de la Recherche Scientifique CNRS
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Individual
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Priority claimed from CA002228801A external-priority patent/CA2228801A1/fr
Priority claimed from CA002256945A external-priority patent/CA2256945A1/fr
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    • C07—ORGANIC CHEMISTRY
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Abstract

La présente invention concerne de nouveaux composés ioniques de bas point de fusion dont le cation est de type onium possédant au mois un hétéroatome tel que N, O, S ou P portant la charge positive et dont l'anion inclut, en totalité ou en partie, au moins un ion imidure du type (FX1O)N-(OX2F) dans laquelle X1 et X2 sont identiques ou différents et comprennent SO ou PF, et leur utilisation comme solvant et dans des dispositifs électrochimiques. La composition comprend un sel dans lequel la charge anionique est délocalisée, et peut être utile, entre autre, comme électrolyte.

Claims (28)

1. Composé ionique de bas point de fusion dont le cation est de type opium possédant au moins un hétéroatome tel que N, O, S ou P portant la charge positive et dont fanion inclut, en totalité ou en partie, au moins un ion imidure du type (FX1O)N-(OX2F) dans laquelle X1 et X2 sont identiques ou différents et comprennent SO ou PF.
2. Composé selon la revendication 1 dans laquelle le cation de type opium comprend un composé de formule:
un composé de formule un composé de formule un composé de formule dans lesquels W est O, S ou N, et dans lequel N est optionnellement substitué par R1 lorsque la valence le permet;
- R1, R3, R4 sont identiques ou différents et représentent - H;
- les radicaux alkyles, alkényles, oxaalkyles, oxaalkényles, azaalkyles, azaalkényles, thiaalkyles, thiaalkényles, dialkylazo, lesdits radicaux pouvant être linéaires, ramifiés ou cycliques et comprenant de 1 à 18 atomes de carbone;
- les radicaux cycliques ou hétérocycliques aliphatiques de 4 à 26 atomes de carbone comprenant optionnellement au moins une chaîne latérale comprenant un ou plusieurs hétéroatomes;
- les aryles, arylalkyles, alkylaryles et alkénylaryles de 5 à 26 atomes de carbone comprenant optionnellement un ou plusieurs hétéroatomes dans le noyau aromatique;
- les groupes comprenant plusieurs noyaux aromatiques ou hétérocycliques, condensés ou non, contenant optionnellement un ou plusieurs atomes d'azote, d'oxygène, de soufre ou de phosphore, deux groupements R1, R3 ou R4 pouvant former un cycle ou un hétérocycle de 4 à

atomes un ou plusieurs groupements R1, R3 ou R4 sur un même cation peuvent faire partie d'une chaîne polymère;
- R2 et R5 à R9 sont identiques ou différents et représente R1, R1O-, (R1)2N-, R1S-, R1 étant tel que défini précédemment.
3. Composé selon la revendication 2 dans lequel les groupements R1, R3 et R4 peuvent porter un groupement actif en polymérisation.
4. Composé selon la revendication 4 dans lequel le groupement actif en polymérisation comprend les doubles liaisons, les époxydes, ou les fonctions réactives dans les polycondensations.
5. Composé selon la revendication 2 dans laquelle le cation comprend un ion ammonium, imidazolium, pyridinium ou phosphonium non substitué ou substitué
par un groupement alkyle, oxaalkyle ou dialkylamino comprenant de 1 à 8 atomes de carbone.
6. Composé selon la revendication 1 caractérisé en ce que le composé comprend en outre au moins un anion choisi parmi Cl-; Br-; I-; NO3-; M(R10)4- A(R10)6-;
R11O2-, [R11ONZ 1]-, [R11YOCZ2Z3]-, le 4,5-dicyano-1,2,3-triazole, le 3,5-bis(RF)-1,2,4-triazole, le tricyanométhane, le pentacyanocyclopentadiène, le pentakis-(trifluorméthyl)cyclopentadiène, les dérivés de (acide barbiturique et de l'acide de Meldrum et leurs produits de substitutions;
- M est B, Al, Ga ou Bi;
- A est P, As et Sb;
- R10 est un halogène;
- R11 représentant H, F, un groupement alkyle, alkényle, aryle, arylalkyle, alkylaryle, arylalkényle, alkénylaryle, dialkylamino, alcoxy ou thioalcoxy, chacun ayant de 1 à 18 atomes de carbone et étant non substitué ou substitué par un ou plusieurs substituants oxa, thia, ou aza, et dans lesquels un ou plusieurs atomes d'hydrogène sont optionnellement remplacés par un halogène dans une proportion de 0 à 100%, et pouvant optionnellement faire partie d'une chaîne polymère;
- Y représentant C, SO, S=NCN, S=C(CN)2, POR11, P(NCN)R11, P(C(CN)2R11, un groupement alkyle, alkényle, aryle, arylalkyle, alkylaryle, arylalkényle, alkénylaryle possédant de 1 à 18 atomes de carbone et optionnellement substitué par un ou plusieurs substituants oxa, thia ou aza; un groupement dialkylamino N(R10)2;
Z1 à Z3 représentent indépendamment R11, R11YO ou CN, ce groupement pouvant optionnellement faire partie d'une chaîne polymère.
7. Composition électrolytique comprenant au moins un composé ionique selon la revendication 1 en combinaison avec au moins un autre composant comprenant un sel métallique, un polymère polaire et/ou un co-solvant aprotique.
8. Composition électrolytique selon la revendication 7 caractérisée en ce que le cation du sel métallique est choisi parmi le proton, le cation d'un métal alcalin, d'un métal alcalino-terreux, d'un métal de transition ou d'une terre rare.
9. Composition électrolytique selon la revendication 7 caractérisée en ce qu'au moins un sel métallique est un sel de lithium.
10. Composition électrolytique selon la revendication 7 caractérisée en ce que le polymère polaire comprend des unités monomères dérivées de l'oxyde d'éthylène, l'oxyde de propylène, l'épichlorohydrine, l'épifluorohydrine, le trifluoroépoxypropane, l'acrylonitrile, le méthacrylonitrile, les esters et amides de l'acide acrylique et méthacrylique, le fluorure de vinylidène, la N-méthylpyrolidone et les polyélectrolytes de type polycation ou polyanion.
11. Composition électrolytique selon la revendication 10 caractérisé en ce que au moins un des polymères est réticulé lorsque la composition comprend plus d'un polymère.
12. Composition électrolytique selon la revendication 7 caractérisé en ce que le co-solvant aprotique est choisi parmi les éthers di-alkyliques de l'éthylène glycol, du diéthylène glycol, du triéthylène glycol, des polyéthylène glycols de masse comprise entre 400 et 2000; les esters, en particulier ceux de l'acide carbonique, linéaires ou cyclique tels le diméthylcarbonate, le méthyl-éthylcarbonate, le diéthylcarbonate, le carbonate d'éthylène, le carbonate de propylène; les esters comme la .gamma.-butyrolactone, les nitriles comme le glutaronitrile, le 1,2,6-tricyanohexane, les amides comme le diméthylformamide, la N-méthylpyrrolidinone, les sulfamides et sulfonamides ainsi que les mélanges des composés précités.
13. Générateur électrochimique ayant au moins une électrode positive et au moins une électrode négative caractérisé en ce qu'il utilise comme électrolyte une composition électrolytique selon la revendication 7.
14. Générateur électrochimique selon la revendication 13 caractérisé en ce que l'électrode négative contient soit du lithium métallique ou un de ses alliages, soit un composé d'insertion du carbone, en particulier du coke de pétrole ou du graphite, soit un oxyde à bas potentiel d'insertion tel que les spinelles de titane Li 4-x+3y Ti 5-x O12(0 ~ x, y ~ 1), soit un nitrure double d'un métal de transition et de lithium comme Li 3-x Co x N(0 ~ z~1) ou ayant la structure de type antifluorite comme Li3FeN2 ou Li7MnN4, ou leurs mélanges.
15. Générateur électrochimique selon la revendication 13 caractérisé en ce que l'électrode positive contient soit de l'oxyde de vanadium VO x (2 ~ x ~ 2,5), soit de l'oxyde mixte de lithium et de vanadium LiV3O8, soit un oxyde double de cobalt et de lithium optionnellement partiellement substitué de formule générale Li 1-.alpha.Co 1-x+y Ni x Al y (0~x + y ~ 1; 0 ~ y ~ 0,3 ; 0 ~ .alpha. ~ 1), soit un spinelle de manganèse optionnellement partiellement substitué de formule générale Li 1-.alpha. Mn 2-z M z (0 ~ z ~
1) où M = Li, Mg, Al, Cr, Ni, Co, Cu, Ni, Fe, soit un phosphate double de structure olivine ou Nasicon tels que Li 1-.alpha. Fe 1-x Mn x PO4, Li 1-x+2.alpha. Fe 2P 1-x Si x O 4 (0 ~ x, .alpha. ~ 1), soit un sel de l'acide rhodizonique, soit un polydisulfure dérivé de l'oxydation du dimercaptoéthane, du 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-oxadiazole, du 1,2-dimercaptocyclobutène-3,4-dione, ou leurs mélanges.
16. Générateur électrochimique selon la revendication 15 caractérisé en ce qu'au moins une des électrodes est mélangée à la composition électrolytique pour former une électrode composite.
17. Système de stockage de l'énergie électrique de type supercapacité
caractérisé
en ce qu'il utilise comme électrolyte une composition électrolytique selon la revendication 7.
18. Système selon la revendication 17 caractérisée en ce qu'il contient dans au moins une électrode du carbone de grande surface spécifique.
19. Système selon la revendication 17 caractérisé en ce qu'il contient dans au moins une électrode un polymère conjugué.
20. Système selon la revendication 17 caractérisé en ce qu'il contient dans les deux électrodes un polymère conjugué possédant trois degrés d'oxydation.
21. Système selon la revendication 20 caractérisé en ce que le polymère conjugué
est un dérivé du phényl-3-thiophène.
22. Système de modulation de la lumière de type électrochrome comprenant au moins un matériau électrochrome, caractérisé en ce que l'électrolyte est une composition électrolytique selon la revendication 7.
23. Système de modulation selon la revendication 22 caractérisé en ce que le matériau électrochrome est déposé sur une couche d'un semi-conducteur transparent dans le visible dérivé de l'oxyde d'étain ou de l'oxyde d'indium sur un substrat de verre ou d'un polymère.
24. Système de modulation selon la revendication 23 caractérisé en ce que le matériau électrochrome est un oxyde de molybdène, de tungstène, de titane, de vanadium, de niobium, de cérium, d'étain ou leur mélanges.
25. Système de modulation selon la revendication 22 caractérisé en ce que le matériau électrochrome est dissous dans l'électrolyte.
26. L'utilisation d'une composition électrolytique selon la revendication 7 comme milieu pour des réactions chimiques ou électrochimiques mettant en jeu des espèces solubles dans ledit milieu.
27. Utilisation selon la revendication 26 caractérisée en ce qu'elle est utilisée comme milieu pour les réactions de Diels-Alder, de Friedel-Craft, d'aldolisation mixte, de condensation, de polymérisation, et pour les substitutions nucléophiles et électrophiles.
28. Utilisation selon la revendication 26 caractérisée en ce que la composition contient un cation onium chiral permettant de réaliser des réactions énantionsélectives.
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