Salts of perfluorinated amides and their uses as ionic conductive materials

Abstract

Abstract Ionic compounds consisting of an amide or one of its salts comprising an anionic part in association with at least one cationic part M<+>m in a number sufficient to provide electronic neutrality to the compound, wherein M = hydroxonium, nitrosonium NO<+>, ammonium -NH4<+>, a metallic cation with a valency m, an organic cation with a valency m, or an organometallic cation having a valency m, and the anionic part corresponds to the formula Rf-S(O)x-N<->-Z in which -S(O)x- = sulphonyl group -SO2- or sulphinyl group -SO-; Rf = a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl or a radical of formula RACF2-, RACF2CF2-, RaCF2CF(CF3)- or CF3C(Ra)F in which Ra = a non-perhalogenated organic radical; Z = an electron-attracting radical having a Hammett parameter at least equal to that of a phenyl radical and selected from (i) -CN, -NO2, -SCN, -N3, -CF3, R'FCH2- (R'f = perfluorinated group), fluoroalkyloxy group, or fluoroalkylthioxy group; (ii) radicals comprising one or more aromatic rings optionally containing at least one N, O, S or P atom, these rings optionally carrying condensed-on rings or at least one substituent selected from halogens, -CN, -NO2, -SCN, -N3, -CF3, CF3CH2-, CF2=CF-O-, CF2=CF-S-, perfluoroalkyl groups, fluoroalkyloxy groups, fluoroalkylthiooxy groups, alkyl radicals, alkenyl radicals, oxa-alkyl, oxa-alkenyl, azaalkyl, aza-alkenyl, thia-alkyl, thia-alkenyl, polymeric radicals, radicals with at least one cationic ionophoric group and/or at least one anionic ionophoric group; wherein a substituent Z may be a monovalent radical, part of a multivalent radical carrying several groups -Rf-S(O)x-N-, or a segment of a polymer; or Z = a radical Rd-Y- in which Y = a sulphonyl, sulphinyl or phosphoryl group and Rd is selected from (a) alkyl, alkenyl, aryl, arylalkyl, alkylaryl, alkenylaryl, alicyclic or heterocyclic radicals including polycyclic radicals; (b) alkyl or alkenyl radicals containing at least one ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group; (c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals in which the aromatic rings and/or at least one substituent on the ring may contain heteroatoms such as N, O or S; (d) radicals containing condensed aromatic rings which may optionally contain at least one heteroatom selected from N, O or S; (e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of C atoms carrying at least one halogen is at most equal to the number of non-halogenated C atoms, the C atom bonded to Y is non-halogenated if Y = -SO2-, and these groups may contain ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate functional groups; (f) radicals RcC(R')(R")-O- in which Rc is a perfluoroalkyl radical and R' and R" independently = H or a radical as defined in (a), (b), (c) or (d) above; (g) radicals (Rb)2N- in which the radicals (Rb) (same or different) are as defined in (a), (b), (c), (d) and (e) above, one of the radicals Rb may = H or the two radicals Rb together with the N atom may complete a ring; (h) radicals constituting a polymer chain; or (i) radicals with one or more cationic ionophoric groups and/or one or more anionic ionophoric groups; provided that a substituent Rb may be a monovalent radical, part of a multivalent radical carrying several groups RFS(O)x-N-Y-, or a segment of a polymer; and that if Y = sulphonyl or carbonyl and Rd is a radical as defined in (A) then RF = RaCF2-, RACF2CF2-, RaCF2CF(CF3)-, CF3C(Ra)F- or 1-2 C perhaloalkyl group.

Inventors

• 👤 Michel Armand
• 👤 Yves Choquette
• 👤 Michel Gauthier
• 👤 Christophe Michot

Bibliographic Details