US 6,319,428 B1 · Perfluorinated amide salts and their uses as ionic conducting materials

Electrochemical generator comprising a negative electrode and a positive electrode both separated by an electrolyte, characterized in that the electrolyte is a material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an amionium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms.

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A supercapacitor using at least one carbon electrode with high specific surface, or at least an electrode containing a redox polymer, with an electrolyte material, in which the electrolyte is a material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalfylthioxy groups, alkyl alkenyl oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur,
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenatod when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and a) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more catonic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms.

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Use of a material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
wherein the material is used for p or n doping of an electronically conductive polymer, by addition to at least a halogenated hydrocarbon and sulfonic anhydride solution.

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Electrochrome device in which the electrolyte is a material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms.

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Electronically conductive material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrlty thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallie cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2═, CF2—CF—O—, CF2═CF—S—, perfuoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
c) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional others thioether, amine, imine, carboxyl, cabonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and c) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms, characterized in that the cationic part of the ionic compound is a polycation consisting of a doped conjugated polymer “p”.

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Electronically conductive material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m sufficicent number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO30 , an ammonium —NH+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an elcctro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl arylkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the nunmber of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are indepedently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurity of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms, characterized in that the substituent Z of the ionic compound comprises an alkyl chain having 6 to 20 carbon atoms.

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An ionically conducdng material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to tho formula RF—SOXN−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a salfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nucli optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkeniyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalont radical, part of a multivalent radical carying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one hetoroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryt or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imino, carboxyl, caibonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinatcd radical and R′ and R″ are independently from one mother, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and c) above, one of the RB may be a hydrogen atom, or the two radicals RB together fonn a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms,
characterized in that M is an organic onium cation selected from the group consisting of R3O+(oxonium), NR4+(ammonium), RC(NHR2)2+(amidinium), C(NHR2)3+(guanidinium), C5R6N+(pyridinium), C3R5N2+(imidazolium), C2R4N3+(triazolium), C3R7N2+(imidazolinium), SR3+(sulfonium), PR4+(phosphonium), IR2+(iodonium), (C6R5)3C+(carbonium), the radicals R independently representing H or a radical selected from the group consisting of:
alkyl, alkenyl, oxa-alkyl oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl, sila-alkyl, sila-alkenyl, aryl, arylalkyl, alkylaryl, alkenylaryl radicals, dialkylamino radicals and dialkylazo radicals;
cyclic or heterocyclic radicals optionally comprising at least one lateral chain comprising heteroatoms such as nitrogen, oxygen, sulfur;
cyclic or heterocyclic radicals optionally comprising heteroatoms in the aromatic nuclei;
groups comprising a plurality of aromatic or heterocyclic, condensed or non-condensed nuclei, optionally containing at least one nitrogen, oxygen, sulfur or phosphorus atom;
with the proviso that a plurality of radicals R may together form aliphatic or aromatic cycles optionally enclosing the center carrying the cationic charge and characterized in that M is an organic onium cation that is part of a recurring unit of a polymer.

22 more elements

An ionically conducting material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts therof, comprising an anionic pat associated with at least one calionic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinatcd radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perufloroaklyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, iminee, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogon is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanato groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are indpdently from one another, an hydrogen atom or a radical as dcfined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and c) above, one of the RB may be a hydrogen atom, or the two radicals RB togother form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RAC2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms,
characterized that M is an organic onium cation selected from the group consisting of R3O+(oxonium), NR4+(ammonium), RC(NHR2)2+(amidinium), C(NHR2)3+(guanidinium), C5R6N+(pyridinium), C3R5N2+(imidazolium), C2R4N3+(triazolium), C3R7N2+(imidazolinium), SR3+(sulfonium), PR4+(phosphonium), IR2+(iodonium), (C6R5)3C+(carbonium), the rdicals R independently representing H or a radical selected from the group consisting of:
alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl, sila-alkyl, sila-alkenyl, aryl, arylalkyl, alkylaryl, alkenylaryl radicals, dialkylamino radicals and dialkylazo radicals;
cyclic or heterocyclic radicals optionally comprising at least one lateral chain comprising heteroatoms such as nitrogen, oxygen, sulfur,
cyclic or heterocyclic radicals optionally comprising heteroatoms in the aromatic nuclei;
groups comprising a plurality of aromatic or heterocyclic, condensed or non-condensed nuclei, optionally containing at least one nitrogen, oxygen, sulfur or phosphorus atom;
with the proviso that a plurality of radicals R may together form aliphatic or aromatic cycles optionally enclosing the center carrying the cationic charge and characterized in that the cation M is a group having a bond —N═N—, —N═N+, a sulfonium group, an iodonium group, or a substituted or non-substituted arene-ferocenium cation, optionally incorporated in a polymer network.

22 more elements

An ionically conducting material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterzed in that M is a hydroxonium, a nitrosonium NO+, an ammionium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphoms atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogen, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophonic group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals corprising condensed aromatic cycles which optionally comprise at least one heteroatom selected fronn nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, alylalkyl alkylaryl or alkenylaryl radicals in which the number of carbon atoms carryng at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional other, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above;
one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms,
characterized in that M is an organic onium cation selected from the group consisting of R3O+(oxonium), NR4+(ammonium), RC(NHR2)2+(amidinium), C(NHR2)3+(guanidinium), C5R6N+(pyridinium), C3R5N2+(imidazolium), C2R4N3+(triazolium), C3R7N2+(imidazolinium), SR3+(sulfonium), PR4+(phosphonium), IR2+(iodonium), (C6R5)3C+(carbonium), the radicals R independently representing H or a radical selected from the group consisting of:
alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl, sila-alkyl, sila-alklenyl, aryl, arylalkyl, alkylaryl, alkenylaryl radicals, dialkylamino radicals and dialkylazo radicals;
cyclic or heterocyclic radicals optionally comprising at least one lateral chain comprising heteroatoms such as nitrogen, oxygen, sulfur;
cyclic or heterocyclic radicals optionally comprising heteroatoms in the aromatic nuclei;
groups comprising a plurality of aromatic or heterocyclic, condensed or non-condensed nuclei, optionally containing at least one nitrogen, oxygen, sulfur or phosphorus atom;
with the proviso that a plurality of radicals R may together forn aliphatic or aromatic cycles optionally enclosing the center carrying the cationic charge and characterized in that M is a cation that is a diaryliodonium cation, a dialkylaryliodonium cation, a triarylsulifonium cation, a trialkylaryl sulfonium cation, or a substituted or non-substituted phenacyl-alkyl sulfonium cation.

23 more elements

An ionically conducting material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the fomula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radical, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selectcd from the group consisting of:
a) alkyl or alkenyl radicals aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, ayl arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″) in which RC is an alkly perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together fonn a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophonic groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carring a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms,
characterized in that M is an orgmiic onium cation selected from the group consisting of R3O+(oxonium), NR4+(ammonium), RC(NHR2)2+(amidinium), C(NHR2)3+(guanidinium), C5R6N+(pyridinium), C3R5N2+(imidazolium), C2R4N3+(triazolium), C3R7N2+(imidazolinium), SR3+(sulfonium), PR4+(phosphonium), IR2+(iodonium), (C6R5)3C+(carbonium), the radicals R independently representing H or a radical selected from the group consisting of:
alkyl, alkenyl, oxa-alkyl oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl, sila-alkyl, sila-alkenyl, aryl, arylalkyl, alkylaryl, alkenylaryl radicals, dialkylamino radicals and dialkylazo radicals;
cyclic or heterocyclic radicals optionally comprising at least one lateral chain comprising heteroatoms such as nitrogen, oxygen, sulfur;
cyclic or heterocyclic radicals optionally comprising heteroatoms in the aromatic nuclei;
groups comprising a plurlity of aromatic or heterocyclic, condensed or non-condensed nuclei, optionally containing at least one nitrogen, oxygen, sulfur or phosphorus atom;
with the proviso that a plurality of radicals R may together fonn aliphatic or aromatic cycles optionally enclosing the center carrying the cationic charge and characterized in that M is an organic cation, incorporating a group 2,2′(azobis(2-2′-imidazolinio-2-yl)propane)2+ or 2,2′-2+azobis(2-amidiniopropane)2+.

22 more elements

An ionically conducting material, comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOx—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic lonophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
further characterized in that the cation is a metallocenium, selected from the group consisting of cations derived from ferrocene, titanocene, zirconocene, indenocenium cations, arene metallocenium cations, cations of transition metals complexed with phosphine ligands optionally having a chirality and organometallic cations having one or more alkyl or aryl groups covalently fixed to an atom or a group of atoms, said cations optionally being part of a polymer chain.

17 more elements

An ionically conducting material, comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosoniurn NO+, an annmonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
further characterized in that Z represents a recurring unit of a polymer chain.

17 more elements

An ionically conducting material, comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophonrc group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
further characterized in that the substituent Z is selected from the group consisting of —OCnF2n+1, —OC2F4H, —SCnF2n+1 and —SC2F4H, —OCF═CF2, —SCF═CF2 and CnF2n+1CH2−n being a whole number from 1 to 8.

17 more elements

Ionically conductive material comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electrotnic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-motallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N+—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl oxa-alkyl, aza-akyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (RF being a perfluorinated radical) or a fluroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur,
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrmgon, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional other, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
characterized in that the solvent is a crosslinked or non-cross-linked solvating polymer, which may carry grafted ionic groups.

17 more elements

Ionically conductive material, comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
further characterized in that the solvent essentially consists of a liquid aprotic solvent and a polar polymer solvent comprising units containing at least one heteroatom selected from sulfur, oxygen, nitrogen and fluorine.

17 more elements

Ionically conductive material, comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)x—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
further characterized in that it additionally contains at least one second salt.

17 more elements

Ionically conductive material, comprising an ionic compound in a solvent, wherein said ionic compound consists of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M+m in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation having a valency m, an organic onium cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula RF—SOX—N−—Z in which:

the group —S(O)X— represents a sulfonic group —SO2— or a sulfinyl group —SO—;
RF is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae RACF2—, RACF2CF2—, RACF2CF(CF3)— or CF3C(RA)F— in which RA— represents a non-perhalogenated organic radical;
Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:
j) —CN, —NO2, —SCN, —N3, —CF3, R′FCH2— (R′F being a perfluorinated radical) or a fluoroalkylthioxy radical,
jj) radicals comprising one or more aromatic nuclei optionally containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei optionally being condensed nuclei and/or said nuclei optionally carrying at least one substituent selected from halogens, —CN, —NO2, —SCN, —N3, —CF3, CF3CH2—, CF2═CF—O—, CF2═CF—S—, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;
with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RF—S(O)X—N—, or a polymer segment;
or
Z is a radical RD—Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and RD is a radical selected from the group consisting of:
a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic, heterocyclic radicals, or polycyclic radicals;
b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;
c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms selected from nitrogen, oxygen, sulfur;
d) radicals comprising condensed aromatic cycles which optionally comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;
e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at most equal to the number of non-halogenated carbon atoms, the carbon in α position of group Y not being halogenated when Y is —SO2—, said radicals optionally comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;
f) radicals RCC(R′)(R″)—O— in which RC is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;
g) radicals (RB)2N—, in which the RB, identical or different, as defined in a), b), c), d) and e) above, one of the RB may be a hydrogen atom, or the two radicals RB together form a bivalent radical which forms a cycle with N;
h) radicals consisting of a polymer chain;
i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;
with the proviso that a substituent RD may be a monovalent radical, part of a multivalent radical carrying a plurality of groups RFS(O)X—N—Y—, or a segment of a polymer;
with the proviso that, when Y is a sulfonyl and RD is a radical such as defined in a), RF is RACF2—, RACF2CF2—, RACF2CF(CF3)—, CF3C(RA)F— or a perhaloalkyl radical having 1 to 2 carbon atoms;
further characterized in that it additionally contains a mineral or organic charge in the form of powder or fibres.

17 more elements

Perfluorinated amide salts and their uses as ionic conducting materials

Life of this patent

Perfluorinated amide salts and their uses as ionic conducting materials

Life of this patent

Abstract

Claims46