Muliti-ionic organic compounds, compositions, and membranes comprising same, and processes for producing same

Abstract

The invention relates to a compound comprising at least two cations derived from a quaternary ammonium or an organic amidine, guanidine or phosphazene superbase, paired with at least two non-delocalized anions. The invention also relates to compositions comprising the compound and a polymer, to membranes comprising the composition, and to processes for producing same.

Description

[0001] MULTI-IONIC ORGANIC COMPOUNDS, COMPOSITIONS AND MEMBRANES COMPRISING THEM, AND PROCESSES FOR THEIR MANUFACTURE RELATED APPLICATION This application claims priority, under applicable law, from Canadian patent application number 3,236,442 filed on April 25, 2024, the contents of which are incorporated herein by reference in their entirety and for all purposes. TECHNICAL FIELD Polyionic molecules and their salts, compositions and membranes comprising them, as well as processes for their manufacture. PRIOR TECHNOLOGY Ion exchange membranes, for example anion exchange membranes, can be used for the separation and / or purification of acidic compounds. These acids may be present as salts in solutions containing other elements such as metals, etc.For example, this type of solution can include processing residues from industrial processes such as electrodeposition / galvanizing, metal etching, metal pickling, the production of inorganic compounds like titanium oxides, etc. One of the processes used in the separation of acidic compounds with this type of membrane operates by diffusion dialysis, that is, based on the principle of osmotic pressure between two solutions. The type of membrane used in these processes generally comprises a polymer containing cationic groups. The manufacture of these membranes typically involves several synthesis steps, which increases production costs. Some anion exchange membranes can also be used in electrolyzers. These membranes then act as a barrier around the electrodes to separate the reactants present while allowing the transport of anions essential for the device's operation.Therefore, there is a need for the development of new types of anion exchange membranes possessing at least one advantage over the other membranes described above. SUMMARY According to a first aspect, the present technology relates to a composition comprising a polymer and a compound comprising at least two cations derived from a quaternary ammonium compound or an organic superbase of amidine, guanidine, or phosphazene paired with at least two non-delocalized anions, preferably of an organic superbase of amidine, guanidine, or phosphazene paired with at least two non-delocalized anions. In one embodiment, the compound has Formula I: in which A is chosen from the groups C6-C 14 arylene and C5-C 14 possibly substituted heteroarylene, the C6-C groups 14 arylene and C5-C 14 heteroarylene being monocyclic or polycyclic, fused or not; R +is independently at each occurrence an organic group comprising a cation derived from a quaternary ammonium or an organic superbase such as amidine, guanidine, or phosphazene; X- is a non-delocalized anion; and n is an integer chosen from 2 to 6. In one embodiment, R + is an organic group comprising a cation derived from an organic superbase amidine, guanidine, or phosphazene. In another embodiment, at least one R + is a grouping of Formula II, III or IV:

[0002] in , L 1 is a linear or branched C1-C6 alkylene group or is absent and A is bonded to N + by a covalent bond; R 2 is independently at each occurrence a linear or branched C1-12 alkyl group, substituted or unsubstituted, or at least two R 2together with their adjacent atom(s) form a saturated or partially unsaturated heterocycle with one or more rings and possessing from 5 to 12 members. In one embodiment, at least one R + is a Formula II grouping. According to an alternative mode, at least one R + is a Formula III grouping. According to another alternative mode, at least one R + is a grouping of Formula IV. In one embodiment, at least one R + comprises a cation selected from the cations of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP), tert-butylimino-tri(pyrrolidino)phosphorane (BTPP), and tert-butylimino-tris(dimethylamino)phosphorane (P1-t-Bu), preferably DBU. In some embodiments, at least one R +is chosen from Formulas II(a), II(b) or II(c): in which L 1 is as defined previously, preferably from Formula II(a). According to other embodiments, at least one R + is of Formula III(a): in which L 1 is as defined previously. According to yet other embodiments, at least one R + is chosen from Formulas IV(a), IV(b) or IV(c): in which L 1 is as defined previously. In some embodiments, at least one R + is an organic group comprising a cation derived from a quaternary ammonium, possibly linked to A by a group L 1In one embodiment, the cation derived from a quaternary ammonium is chosen from aromatic or non-aromatic heterocyclic ammoniums having 5 to 10 ring atoms, the heterocycles optionally being substituted, the quaternary ammonium optionally being linked to A by a group L 1 In one embodiment, L 1 is a linear or branched C1-C6 alkylene group, for example, L 1 is a methylene. In another embodiment, A is a C6-C14arylene group, possibly substituted monocyclic or polycyclic, fused or unfused. In another embodiment, A is a C6arylene group, possibly substituted (for example, by one or more methyl groups). According to one embodiment, the compound has the formula I(a), I(b), I(c), I(d), or I(e): + + + in which, (R') +is the cation derived from a quaternary ammonium or an organic superbase such as amidine, guanidine, or phosphazene, and X- is as defined previously. In some embodiments, (R')+ is the cation derived from an organic superbase such as amidine, guanidine, or phosphazene. In some embodiments, the non-delocalized anion is OH-, a halide ion, or a combination of at least two of these; preferably, the non-delocalized anion comprises OH-. In one embodiment, the compound is selected from Compounds 1 to 6: In another embodiment, the compound is present in the composition at a concentration of approximately 10% to approximately 95% by weight, or approximately 30% to approximately 90% by weight, or approximately 40% to approximately 90% by weight, or approximately 50% to approximately 80% by weight, inclusive. In yet another embodiment, the polymer is present in the composition at a concentration of at least 5% by weight, and preferably less than 50% by weight. In one embodiment, the polymer is present in the composition at a concentration within the range of approximately 5% by weight to approximately 90% by weight, or approximately 10% by weight to approximately 70% by weight, or approximately 10% by weight to approximately 60% by weight, or approximately 20% by weight to approximately 50% by weight, inclusive.In some embodiments, the compound is present in the composition at a concentration of at least 50% by weight and the polymer is present in the composition at a concentration of at most 50% by weight. In one embodiment, the polymer is linear or branched. In another embodiment, the polymer is crosslinked. In an alternative embodiment, the polymer is non-crosslinked. In some embodiments, the polymer is selected from polymers based on polyethylene, polypropylene, polybutadiene, polystyrene, fluoropolymer, substituted or unsubstituted polynorbornene, or a copolymer thereof, synthetic or natural rubber, optionally comprising at least one crosslinkable or crosslinked group. In one embodiment, the polymer is chosen from among the fluoropolymers (for example, polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF) and poly(vinylidene fluoride-co-hexafluoropropylene) (PVDF-HFP)).In another embodiment, the polymer is selected from polymers based on polyethylene, polypropylene, polybutadiene, polystyrene, substituted or unsubstituted polynorbornene, or a copolymer thereof (such as polyethylene, poly(ethylene-co-norbornene), poly(styrene-butadiene-styrene) or poly(styrene-co-butadiene) (SBS), etc.). In yet another embodiment, the polymer is a synthetic or natural rubber (such as natural rubbers, carboxylated nitrile rubber (XNBR), hydrogenated nitrile rubber (HNBR), ethylene-propylene-diene polymer (EPDM), acrylonitrile-butadiene-styrene polymer (ABS), etc.). In other embodiments, the polymer is a polyether-type polymer, optionally branched and / or crosslinked, for example, a polymer based on poly(ethylene oxide) (POE), poly(propylene oxide) (POP), or a combination or copolymer thereof, optionally branched and / or crosslinked.According to yet other embodiments, the polymer is a sequenced copolymer composed of at least one polyether segment and optionally at least one crosslinkable segment, the polyether segment being chosen from homo- or copolymers having repeating units of formula -(CH2CH(R). 3 )O)y- in which R 3 is chosen from a hydrogen atom, a C1-C10 alkyl group or a –(CH2-OR) group 4 R 5 ), R 4 is (CH2- CH2-O)m, R 5is chosen from a hydrogen atom and a C1-C10 alkyl group, y is an integer chosen from the range of 10 to 200,000; and m is an integer chosen from the range of 0 to 10. For example, the crosslinkable segment of the copolymer is a polymer segment comprising at least one functional group that can be crosslinked multidimensionally by irradiation or heat treatment. In another embodiment, the compound comprises at least one crosslinkable or crosslinked group, the crosslinking occurring between compounds or between the compound and the polymer. According to other embodiments, the composition further comprises an additional component chosen from the group consisting of solvents, inorganic particles, plasticizers, and a combination of at least two of these.In one embodiment, the inorganic particles comprise glass particles, glass-ceramic particles, ceramic particles, or a combination of two or more of these. Alternatively, the inorganic particles comprise a compound having a garnet-like, NASICON, LISICON, thio-LISICON, LIPON, perovskite, antiperovskite, or argyrodite-type structure, or comprise a compound of the MPS, MPS-O, MPSX, or MPSOX type (where M is an alkali or alkaline earth metal, and X is F, Cl, Br, I, or a combination of at least two of these) in crystalline, amorphous, and / or glass-ceramic form, or a mixture of at least two of these. In one embodiment, the ceramic or glass-ceramic is a ceramic based on an oxide, sulfide, oxysulfide, or a combination of at least two of these. According to one embodiment, the sulfide-based ceramic is chosen from Li. 10 GeP2S 12 , Li6PS5Cl, Li2S–P2S5, Li7P3S 11, It 9,54 If 1,74 P 1,44 S 11,7 Cl 0,3 , It 9,6 P3S 12 and He 3.25 P 0,95S4, preferably Li6PS5Cl. In another embodiment, the inorganic particles comprise a filler additive selected from the group consisting of titanium dioxide (TiO2), alumina (Al2O3), and silicon dioxide (SiO2) particles or nanoparticles. In one embodiment, the composition is a solid or semi-solid composition, preferably a solid composition. In another aspect, the present technology also relates to a membrane comprising the composition as defined herein, in the form of a solid film. In one embodiment, the membrane is an anion exchange membrane, for example, an anion exchange membrane for diffusion dialysis. In another embodiment, the membrane is an anion exchange membrane for use in an electrolyzer.In yet another aspect, the present technology relates to a process for preparing a membrane as defined herein, the process comprising the steps of: (i) combining the compound with the polymer and optionally an additional component as defined previously to obtain a composite; and (ii) forming the membrane from the composite obtained in step (i). In one embodiment, step (i) comprises mixing the compound with the polymer by extrusion. In another embodiment, step (ii) is carried out by extrusion through a die.In yet another aspect, the present technology also relates to a process for preparing a membrane as defined herein, the process comprising the steps of: (i) mixing the compound with the polymer and optionally an additional component as defined above in the presence of a solvent to obtain a composition; (ii) coating the composition obtained in step (i) onto a substrate; (iii) removing the solvent; and (iv) removing the substrate to produce the membrane. In one embodiment, steps (ii) and (iii) of this process are carried out sequentially, simultaneously, or partially overlapping in time. In another embodiment, the solvent is selected from an aromatic solvent or a halogenated solvent (such as toluene, chlorobenzene, and dichlorobenzene). In one embodiment, the substrate is selected from polymer supports (such as polyethylene, polypropylene, etc.).In another embodiment, step (i) is carried out at a temperature in the range of approximately 20°C to approximately 50°C, or at room temperature. In yet another embodiment, the coating step is carried out by at least one squeegee coating method, a transfer interval coating method, a reverse transfer interval coating method, a printing method such as etching, or a slit coating method, preferably by at least one squeegee coating method or a slit coating method. In one embodiment of the processes described herein, the process further comprises a step of treating the membrane with a metal hydroxide solution (such as KOH). In another embodiment of the processes described herein, the process further comprises a step of crosslinking the polymer, the compound, or both, for example, within the membrane. BRIEF DESCRIPTION OF THE FIGURES Figure 1 shows the NMR spectrum.1 H of Compound 1 in D2O. Figure 2 shows the NMR spectrum 1 H of Compound 2 in D2O. Figure 3 shows the applied force during extrusion as a function of the compound content according to Example 2(b). Figure 4 shows the solid-phase proton NMR spectrum for Film 1, both dry and hydrated. Figure 5 shows the logarithmic plots of signal attenuation as a function of B in the NMR scattering experiments for Film 1, both dry and hydrated. Figure 6 shows the NMR spectrum. 13Figure 7 shows the FTIR spectrum of Compound 3(a) in solid phase as described in Example 1(c). Figure 7 shows the FTIR spectrum of Compound 3(a) obtained with 0.52 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene and 0.67 equivalents of 4-vinylpyridine as described in Example 1(c). Figure 8 shows the FTIR spectrum of Compound 3(a) obtained with 1.0 equivalent of 1,8-diazabicyclo[5.4.0]undec-7-ene and 1.0 equivalent of 4-vinylpyridine as described in Example 1(c). Figure 9 shows the FTIR spectrum of Compound 3(a) obtained with 3.0 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene and 1.0 equivalent of 4-vinylpyridine as described in Example 1(c). Figure 10 shows the FTIR spectrum of Compound 3(a) obtained with 2.0 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene and 2.0 equivalents of 4-vinylpyridine as described in Example 1(c). Figure 11 shows the FTIR spectrum of Compound 4(a) as described in Example 1(d). Figure 12 shows the FTIR spectrum of Compound 5(a) as described in Example 1(e).Figure 13 shows the FTIR spectrum of Compound 6(a) as described in Example 1(f). Figure 14 shows the NMR spectrum. 1 H of Compound 6(a) in D2O as described in Example 1(f). Figure 15 shows the NMR spectrum 13C of Compound 6(a) in D2O as described in Example 1(f). DETAILED DESCRIPTION The following detailed description and examples are given for illustrative purposes only and shall not be construed as further limiting the scope of the invention. On the contrary, they are intended to cover all alternatives, modifications, and equivalents that may be included as defined by this description. The objects, advantages, and other features of the present ionic compounds, compositions, and membranes comprising them, their methods of preparation, and their uses will be more apparent and better understood upon reading the following non-restrictive description and references to the accompanying figures. All technical and scientific terms and expressions used herein have the same definitions as those generally understood by a person versed in the art of this technology.The definitions of certain terms and expressions used are nevertheless provided below. When the term "about" is used here, it means approximately, in the region of, or around. For example, when the term "about" is used in connection with a numerical value, it modifies it above and below by a variation of 10% from its nominal value. This term can also take into account, for example, the experimental error of a measuring instrument or rounding. Where a range of values ​​is mentioned in this application, the lower and upper bounds of the range are, unless otherwise indicated, always included in the definition. Where a range of values ​​is mentioned in this application, then all intermediate ranges and subranges, as well as individual values ​​included within the ranges of values, are included in the definition.When the article "a" is used to introduce an element in this application, it does not mean "only one," but rather "one or more." Of course, when the description states that a particular step, component, element, or feature "may" or "could" be included, that particular step, component, element, or feature is not required to be included in every embodiment. The chemical structures described herein are drawn according to the conventions of the field. Therefore, when an atom, such as a carbon atom, as drawn, appears to include an incomplete valence, then it is assumed that the valence is satisfied by one or more hydrogen atoms, even if they are not explicitly drawn. The term "alkyl" used herein refers to saturated hydrocarbons having between one and ten carbon atoms, including linear or branched alkyl groups.Non-limiting examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, tert-butyl, sec-butyl, isobutyl, and so on. When the alkyl group is located between two functional groups, the term alkyl also includes alkylene groups such as methylene, ethylene, propylene, and so on. The terms "Cm-Cnalkyl" and "Cm-Cnalkylene" refer to an alkyl or alkylene group, respectively, having from the indicated number "m" to the indicated number "n" of carbon atoms.The terms "cycloalkyl" or "cycloalkylene" used here refer to a group comprising one or more saturated or partially unsaturated (non-aromatic) carbocyclic rings of three to twelve members in a monocyclic or polycyclic system, including spiro (sharing one atom) or fused (sharing at least one bond) carbocycles, and may optionally be substituted. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentene-1-yl, cyclopentene-2-yl, cyclopentene-3-yl, cyclohexyl, cyclohexene-1-yl, cyclohexene-2-yl, cyclohexene-3-yl, cycloheptyl, and so on. When the cycloalkyl group is located between two functional groups, the term cycloalkylene may also be used. The terms "Cm-Cycloalkyl" and "Cm-C" may also be used. nCycloalkylene refers respectively to a cycloalkyl or cycloalkylene group having from the specified number "m" to the specified number "n" of carbon atoms in the ring structure. As used here, the terms heterocycloalkyl or heterocycloalkylene refer to a group comprising a saturated or partially unsaturated (non-aromatic) carbocyclic ring of three to twelve members in a monocyclic or polycyclic system, including spiro (sharing one atom) or fused (sharing at least one bond) carbocycles, and may optionally be substituted, where one or more atoms in the ring structure are substituted or unsubstituted heteroatoms (e.g., N, O, S, or P) or groups containing such heteroatoms (e.g., NH, NR). x (R xis an alkyl, acyl, aryl, heteroaryl, or cycloalkyl group), PO2, SO2, SO2, and other similar groups. Heterocycloalkyl groups may be bonded to a carbon atom or to a heteroatom (e.g., via a nitrogen atom) when possible. The term heterocycloalkyl includes both unsubstituted and substituted heterocycloalkyl groups. When the heterocycloalkyl group is located between two functional groups, the term heterocycloalkylene may also be used. The terms "Cm-Cnheterocycloalkyl" and "Cm-Cnheterocycloalkylene" refer, respectively, to a heterocycloalkyl or heterocycloalkylene group having from the indicated number "m" to the indicated number "n" of carbon atoms and heteroatoms in the ring structure.As used here, the terms "aryl" or "aromatic" refer to an aromatic group possessing 4n+2 π(pi) electrons, where n is an integer from one to three, in a monocyclic or conjugated (fused or unfused) polycyclic system with a total of six to twelve ring members. A polycyclic system includes at least one aromatic ring. This ring may be directly bonded or attached by a C1-C3 alkyl group. The term "aryl" or "aromatic" also includes both substituted and unsubstituted groups. Examples of aryl groups include, without limitation, phenyl, benzyl, phenethyl, 1-phenylethyl, tolyl, naphthyl, biphenyl, terphenyl, indenyl, benzocyclooctenyl, benzocycloheptenyl, azulenyl, acenaphthylenyl, fluorenyl, phenanthrenyl, anthracenyl, perylenyl, and so on. When the aryl group is located between two functional groups, the term arylene may also be used. The terms "C. m -C naryl" or "C m -C n aromatic” and “C m -C n "Arylene" refers respectively to an aryl or aromatic group and arylene having from the specified number "m" to the specified number "n" of carbon atoms in the ring structure. The terms "heteroaryl," "heteroarylene," or "heteroaromatic" refer to aromatic groups having 4n+2 π(pi) electrons, where n is an integer from one to three, in a conjugated monocyclic or polycyclic system (fused or unfused) and having five to twelve ring members, including one to six substituted or unsubstituted heteroatoms (e.g., N, O, or S) or groups comprising such heteroatoms (e.g., NH, NR). x (R xis an alkyl, acyl, aryl, heteroaryl, or cycloalkyl group), SO, and other similar groups). A polycyclic system includes at least one heteroaromatic ring. Heteroaryls may be directly bonded or attached by a C1-C3 alkyl group (also called a heteroarylalkyl or heteroaralkyl group). Heteroaryl groups may be bonded to a carbon atom or to a heteroatom (e.g., via a nitrogen atom), when possible. The term "Cm-Cnheteroaryl" refers to a heteroaryl group having from the indicated number "m" to the indicated number "n" of carbon atoms and heteroatoms in the ring structure. As used here, the term "substituted" means that one or more hydrogen atoms on the designated group are replaced by a suitable substituent.Examples of substituents include halogen atoms (i.e., F, Cl, Br, or I) and cyano, amide, nitro, trifluoromethyl, lower alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, lower alkoxy, aryloxy, benzyloxy, benzyl, alkoxycarbonyl, sulfonyl, sulfonate, silane, siloxane, phosphonato, phosphinato, and other similar groups. These substituents may also be substituted where possible, for example, if the group contains an alkyl, alkoxy, aryl, or other similar group. The present technology relates to a compound comprising at least two cations derived from a quaternary ammonium or an organic superbase such as amidine, guanidine, or phosphazene paired with two non-delocalized anions, and to compositions comprising such a compound. Preferably, the cations are derived from an organic superbase amidine, guanidine or phosphazene paired with at least two non-delocalized anions.For example, the compound is stable up to a temperature of at least 200°C. In one embodiment, the compound can be substantially insoluble in water when present in a membrane while remaining hygroscopic. Preferably, the cations derived from a quaternary ammonium or from the superbase amidine, guanidine, or phosphazene of the compound are linked by a nitrogen (ammonium) atom to a multifunctional group, preferably an aryl or heteroaryl group. Examples of compounds include those of Formula I: in which A is chosen from the groups C6-C 14 arylene and C5-C 14 possibly substituted heteroarylene, the C6-C groups 14 arylene and C5-C 14 heteroarylene being monocyclic or polycyclic, fused or not; R +is independently at each occurrence an organic group comprising the cation derived from a quaternary ammonium or an organic superbase amidine, guanidine, or phosphazene; X- is a non-delocalized anion; and n is an integer chosen from 2 to 6, or from 2 to 4. According to an example, R + is an organic group comprising a cation derived from an organic superbase amidine, guanidine, or phosphazene. Preferably, at least one organic group R + is chosen from the Formula II, III or IV groups: in which, L 1 is a linear or branched C1-C6 alkylene group or is absent and A is bonded to N + by a covalent bond; R 2 is independently at each occurrence a grouping C 1-12 linear or branched alkyl, substituted or unsubstituted, or at least two R 2together with their adjacent atom(s) form a saturated or partially unsaturated heterocycle with one or more rings and possessing 5 to 12 members. For example, at least one R + is of Formula II. According to another example, at least one R + is of Formula III. Alternatively, at least one R + is of Formula IV. For example, the cation derived from the superbase amidine, guanidine, or phosphazene can have an acyclic, monocyclic, or polycyclic structure. According to some embodiments, at least one R +includes a cation selected from the cations of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 2-tert-butyllimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP), tert-butyllimino-tri(pyrrolidino)phosphorane (BTPP), and tert-butylimino-tris(dimethylamino)phosphorane (P1-t-Bu), preferably DBU. In some examples, at least one R + is chosen from Formulas II(a), II(b) or II(c): in which L 1 is such as defined previously, preferably from Formula II(a). Alternatively, at least one R + is of Formula III(a): in which L 1 is as defined previously. Or, at least one R + can be chosen from Formulas IV(a), IV(b) or IV(c): in which L 1 is as defined previously. According to some examples, at least one R +is an organic group comprising a cation derived from a quaternary ammonium, possibly linked to A by a group L 1 Examples of cations derived from a quaternary ammonium include aromatic or non-aromatic heterocyclic ammoniums with 5 to 10 ring atoms, the heterocycles being optionally substituted, the quaternary ammonium possibly being linked to A by an L group 1 According to certain embodiments of the examples above, L 1 is a linear or branched C1-C6 alkylene group, for example, L 1 is a methylene. According to some examples, A is a C6-C group 14arylene, possibly substituted, mono- or polycyclic, fused or unfused. For example, A could be a C6-arylene group, possibly substituted (for example, by one or more methyl groups). According to some embodiments, the compound has the formula I(a), I(b), I(c), I(d), or I(e): + + + in which, (R') + is the cation derived from a quaternary ammonium or an organic superbase such as amidine, guanidine, or phosphazene, and X- is as defined previously. In some examples, (R')+ is the cation derived from an organic superbase such as amidine, guanidine, or phosphazene. In a preferred embodiment, the non-delocalized anion is OH-, a halide ion, or a combination of at least two of these. Preferably, the non-delocalized anion comprises OH-. Examples of multi-ionic compounds as described herein include, without limitation, Compounds 1 through 6: The composition of the present technology comprises at least one compound as defined herein and at least one polymer. Preferably, the compound is present in the composition at a concentration of approximately 10% to approximately 95% by weight, or approximately 30% to approximately 90% by weight, or approximately 40% to approximately 90% by weight, or approximately 50% to approximately 80% by weight, inclusive. The polymer may be present in the composition at a concentration of at least 5% by weight, for example, at a concentration within the range of approximately 5% by weight to approximately 90% by weight, or approximately 10% by weight to approximately 70% by weight, or approximately 10% by weight to approximately 60% by weight, or approximately 20% by weight to approximately 50% by weight, inclusive.According to a preferred method, alone or in combination with either of the preceding methods, the compound is present in said composition at a concentration of at least 50% by weight, and the polymer is present in said composition at a concentration of at most 50% by weight. The polymer is not particularly restricted and may be selected from polymers known for membrane formation. The polymer will normally be in solid form or will form a solid when mixed with the compound and / or when crosslinked. According to one embodiment, the polymer is linear or branched. According to another embodiment, the polymer is crosslinked. Crosslinking may be carried out by various methods, including UV irradiation, heat treatment, microwave irradiation, electron beam irradiation, gamma irradiation, or X-ray irradiation, optionally in the presence of a crosslinking agent, initiator, or catalyst. According to an alternative method, the polymer is uncrosslinked.Examples of polymers include polymers based on polyethylene, polypropylene, polybutadiene, polystyrene, fluoropolymer, substituted or unsubstituted polynorbornene, or a copolymer of two or more of these, synthetic or natural rubber, which may also include at least one crosslinkable or crosslinked group or chain. For example, the fluoropolymer may be polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), or poly(vinylidene fluoride-co-hexafluoropropylene) (PVDF-HFP). According to a preferred method, the polymer is chosen from polymers based on polyethylene, polypropylene, polybutadiene, polystyrene, substituted or unsubstituted polynorbornene, or a copolymer of these (such as polyethylene, poly(ethylene-co-norbornene), poly(styrene-butadiene-styrene) or poly(styrene-co-butadiene) (SBS), etc.).According to another preferred mode, the polymer is a synthetic or natural rubber (such as natural rubbers, carboxylated nitrile rubber (XNBR), hydrogenated nitrile rubber (HNBR), ethylene propylene diene polymer (EPDM), acrylonitrile butadiene styrene polymer (ABS), etc.). Other examples of polymers include polyether-type polymers, such as those based on poly(ethylene oxide) (POE), poly(propylene oxide) (POP), or a combination or copolymer thereof, possibly branched and / or crosslinked, but other compatible polymers are also considered. Examples of such polymers include branched polymers, for example, star polymers or comb polymers such as those described in U.S. Patent No. 7,897,674 B2 (Zaghib et al.) (US'674).According to some examples, the polymer may be a sequenced copolymer composed of at least one polyether segment and possibly at least one crosslinkable segment. For example, the polyether segment is chosen from homo- or copolymers having repeating units of formula -(CH2CH(R). 3 )O)y- in which R 3 is chosen from a hydrogen atom, a C1-C10 alkyl group or a –(CH2-OR) group 4 R 5 ), R 4 is (CH2- CH2-O)m, R 5is chosen from a hydrogen atom and a C1-C10 alkyl group, y is an integer chosen from the range of 10 to 200,000; and m is an integer chosen from the range of 0 to 10. According to another example, the crosslinkable segment of the copolymer is a polymer segment comprising at least one functional group crosslinkable multidimensionally by irradiation (such as electron beam, UV light, etc.), or by heat treatment, or by one of the methods described above. According to other examples, the compound comprises at least one crosslinkable or crosslinked group, the crosslinking occurring between compounds or between the compound and the polymer. According to one example, the composition further comprises an additional component that may be chosen from the group consisting of solvents, inorganic particles, glass particles, ceramic particles (e.g., nanoceramics),Plasticizing agents and other similar components, or a combination of at least two of these. For example, the additional component may be a filler additive and may include metal oxide particles or nanoparticles. For example, the filler additive may include particles or nanoparticles of titanium dioxide (TiO2), alumina (Al2O3), and / or silicon dioxide (SiO2). In another example, the additional component may be inorganic particles including a compound with a garnet-like structure, NASICON, LISICON, thio-LISICON, LIPON, perovskite, antiperovskite, argyrodite, or including a compound of the type MPS, MPSO, MPSX, MPSOX (where M is an alkali or alkaline earth metal, and X is F, Cl, Br, I or a combination of at least two of these) in crystalline, amorphous and / or glass-ceramic form, or a mixture of at least two of these. In another example,the additional component may be inorganic particles of crystalline, amorphous and / or glass-ceramic form, or a mixture of at least two of these and including at least one of the inorganic compounds of formulas MLZO (for example, M7La3Zr2O12, M(7-a)La3Zr2AlbO12, M(7-a)La3Zr2GabO12, M(7-a)La3Zr(2-b)TabO12, and M(7-a)La3Zr(2-b)NbbO12); MLTaO (for example, M7La3Ta2O12, M5La3Ta2O12, and M6La3Ta1,5Y0,5O12); MLSnO (for example, M7La3Sn2O12); MAGP (for example, M1+aAlaGe2-a(PO4)3); MATP (e.g., M1+aAlaTi2-a(PO4)3,); MLTiO (e.g., M3aLa(2 / 3-a)TiO3); MZP (e.g., MaZrb(PO4)c); MCZP (e.g., MaCabZrc(PO4)d); MGPS (e.g., MaGebPcSd such as M10GeP2S12); MGPSO (e.g., MaGebPcSdOe); MSiPS (e.g., MaSibPcSd such as M10SiP2S12); MSiPSO (e.g., MaSibPcSdOe); MSnPS (e.g., MaSnbPcSd such as M10SnP2S12); MSnPSO (e.g., MaSnbPcSdOe); MPS (e.g., MaPbSc such as M7P3S11); MPSO (for example, MaPbScOd); MZPS (for example,MaZnbPcSd); MZPSO (for example, MaZnbPcSdOe); xM2S-yP2S5; xM2S-yP2S5-zMX; xM2S-yP2S5-zP2O5; xM2S-yP2S5-zP2O5-wMX; xM2S-yM2O-zP2S5; xM2S-yM2O-zP2S5-wMX; xM2S-yM2O-zP2S5-wP2O5; xM2S-yM2O-zP2S5-wP2O5-vMX; xM2S-ySiS2; MPSX (for example, MaPbScXd such as M7P3S11X, M7P2S8X, and M6PS5X); MPSOX (for example, MaPbScOdXe); MGPSX (for example, MaGebPcSdXe); MGPSOX (for example, MaGebPcSdOeXf); MSiPSX (for example, MaSibPcSdXe); MSiPSOX (for example, MaSibPcSdOeXf); MSnPSX (for example, MaSnbPcSdXe); MSnPSOX (for example, MaSnbPcSdOeXf); MZPSX (for example, M, a Zn b P c S d X e ); MZPSOX (for example, M a Zn b P c S d O e X f ); M3OX; M2HOX; M3PO4; M3PS4; or M a PO b N c(where a = 2b + 3c - 5); in which M is an alkali metal ion, an alkaline earth metal ion, or a combination thereof, and in which, when M includes an alkaline earth metal ion, the number of M is adjusted to achieve electroneutrality; X is chosen from F, Cl, Br, I, or a combination thereof; a, b, c, d, e, and f are nonzero numbers and are, independently in each formula, selected to achieve electroneutrality; and v, w, x, y, and z are nonzero numbers and are, independently in each formula, selected to obtain a stable compound. In another example, the additional component may be a ceramic or a glass-ceramic. For instance, the additional component may be a sulfide-based ceramic or glass-ceramic such as Li 10 GeP2S 12 , Li6PS5Cl, Li2S–P2S5, Li7P3S 11Li9,54Si1,74P1,44S11,7Cl0,3, Li9,6P3S12, Li3,25P0,95S4, and other similar ceramics and glass-ceramics. In a preferred mode, the composition is solid or semi-solid, preferably solid. The technology also relates to a membrane comprising the composition as described herein in solid film form. Preferably, the membrane is an anion exchange membrane, for example, an anion exchange membrane for diffusion dialysis. Membranes can be prepared from the compositions herein by any process compatible with the elements contained in the composition. An example of a process for preparing a membrane as described herein comprises at least the steps of: (i) combining the compound with the polymer and optionally an additional component as defined above to obtain a composite; and (ii) forming the membrane from the composite obtained in step (i).According to a preferred method, step (i) comprises mixing the compound with the polymer by extrusion. The composite can then be obtained in the form of strands or in some other similar form. Such extrusion can be carried out under general conditions used in composite mixing. For example, the extruder can operate at a temperature between ambient temperature and 200°C. According to another preferred method, step (ii) is carried out by extrusion, for example, through a die. Another example of a process for preparing a membrane as defined herein comprises the steps of: (i) mixing the compound with the polymer and possibly an additional component as defined above in the presence of a solvent to obtain a composition; (ii) coating the composition obtained in step (i) onto a substrate; (iii) removing the solvent; and (iv) removing the substrate to produce the membrane.Alternatively, step (i) does not involve a solvent, and the polymer is replaced by a liquid precursor thereof, which is subsequently polymerized and / or crosslinked to form a solid polymer. According to this process example, steps (ii) and (iii) can be carried out sequentially, simultaneously, or partially overlapping in time. Examples of solvents, when present, can be chosen from an aromatic solvent or a halogenated solvent (such as toluene, chlorobenzene, and dichlorobenzene). The substrate can be chosen from polymer or glass supports, preferably a polymer support, for example, polyethylene, polypropylene, etc. In this process example, step (i) can be carried out at a temperature in the range of approximately 20°C to approximately 50°C, or at room temperature.The coating step can be performed by any known and compatible method, for example, by a squeegee coating method, a transfer interval coating method, a reverse transfer interval coating method, a printing method such as etching, or a slit coating method, preferably by at least one squeegee coating method or one slit coating method. In one embodiment of any of the processes of this technology, the process may further include a compound synthesis step prior to step (i). In one embodiment of any of the processes of this technology, the process may further include a step of treating the membrane with a metal hydroxide solution (such as KOH).In certain embodiments of one of the processes of the present technology, the process further comprises a crosslinking step of the polymer, the compound, or both, for example, in the membrane, for example, polymer crosslinking. EXAMPLES The following examples are for illustrative purposes only and should not be interpreted as further limiting the scope of the invention as contemplated. These examples will be better understood by referring to the accompanying figures. Unless otherwise indicated, all numbers expressing quantities of components, preparation conditions, concentrations, properties, etc., used herein should be understood as modified in all cases by the term "approximately." At a minimum, each numerical parameter should be interpreted in light of the number of significant figures reported and by applying common rounding techniques.Therefore, unless otherwise specified, the numerical parameters stated in this document are approximations that may vary depending on the desired properties. Notwithstanding the fact that the ranges of numerical values ​​and the parameters defining the scope of embodiments are approximations, the numerical values ​​presented in the following examples are reported as accurately as possible. However, any numerical value inherently contains some errors resulting from variations in experiments, test measurements, statistical analyses, etc. Example 1 – Preparation of Compounds (a) Compounds 1 and 1(a) pp 1,4-Bis(bromomethyl)-2,5-Dimethylbenzene (1.0 equivalent) is dissolved in anhydrous dichloromethane (85 equivalents), and then 1,8-Diazabicyclo[5.4.0]undec-7-ene (2.2 equivalents) is added dropwise to the mixture. The mixture is refluxed for 48 hours under a nitrogen atmosphere.The white solid formed is filtered, washed three times with dichloromethane, and then dried under vacuum at room temperature for 4 hours. The compound obtained is the dibromide of Compound 1, designated Compound 1(a). The NMR spectrum. 1 The concentration of Compound 1(a) in D2O is shown in Figure 1. Compound 1 is obtained by contacting Compound 1(a) with a KOH solution (see Example 3). (b) Compounds 2 and 2(a) Compound 2(a) Compound 2 Compound 2 is prepared following the procedure in Example 1(a) where 1,4-bis(bromomethyl)-2,5-dimethylbenzene is replaced by 1,4-bis(bromomethyl)benzene to produce a white solid. The NMR spectrum 1 H of Compound 2(a) (di-bromide) in D2O is shown in Figure 2. Compound 2 is obtained by treating Compound 2(a) in the presence of KOH.

[0003] (c) Compounds 3 and 3(a) 1,8-Diazabicyclo[5.4.0]undec-7-ene (A, between 0.52 and 3 eq.) and 4-vinylpyridine (B, between 0.67 and 2 eq.) are dissolved in anhydrous dichloromethane, and then 1,2,4,6-tetra(bromomethyl)benzene (1.0 equivalent) is added to the mixture. The solution is stirred for 48 to 72 hours at room temperature. The resulting solid is filtered through filter paper and then washed three times with dichloromethane. The solid is transferred to a 250 mL beaker, and 75 mL of ethyl acetate is added. The solution is stirred for 2 hours, then filtered and washed three times with the solvent. The solid is then dried under vacuum for 24 hours at room temperature. The resulting compound is the tetrabromide of Compound 3, designated Compound 3(a). The solid is insoluble and an NMR spectrum 1Therefore, H in solution of Compound 3(a) could not be obtained. Figure 6 shows the 13C NMR spectrum of Compound 3(a) in the solid phase with proton polarization. The structure is also confirmed by the FTIR spectra shown in Figures 7 to 10, for the compounds obtained with the equivalent ratios (A:B) of 0.52:0.67 (Fig. 7), 1:1 (Fig. 8), 3:1 (Fig. 9), and 2:2 (Fig. 10). Compound 3 is obtained by contacting Compound 3(a) with a KOH solution (see Example 3). (d) Compounds 4 and 4(a) Compound 4 is prepared following the procedure of Example 1(c) where 1,2,4,6-tetra(bromomethyl)benzene is replaced by 1,3,5-tri(bromomethyl)benzene and using 2.0 eq. of 1,8-diazabicyclo[5.4.0]undec-7-ene and 1.0 eq. of 4-vinylpyridine. The structure is confirmed by FTIR spectroscopy, the spectrum being shown in Figure 11. Compound 4 is obtained by treating Compound 4(a) in the presence of KOH. (e) Compounds 5 and 5(a) The 4.25 eq. of 4-vinylpyridine and where 1,8-diazabicyclo[5.4.0]undec-7-ene is absent. The structure is confirmed by FTIR spectroscopy, the spectrum being shown in Figure 12. Compound 5 is obtained by treating Compound 5(a) in the presence of KOH. (f) Compounds 6 and 6(a) Compound 6 is prepared following the procedure of Example 1(c) using 3.0 eq. of N-methylpipedirine and 1.0 eq. of 4-vinylpyridine. The structure is confirmed by FTIR spectroscopy, the spectrum of which is shown in Figure 13. The NMR spectra 1 H and NMR 13The C of Compound 6(a) in D2O are shown in Figures 14 and 15. Compound 6 is obtained by treating Compound 6(a) in the presence of KOH. Example 2 – Film Preparation (a) By Wet Coating The pestle-ground powder of Compound 1(a) is mixed with chlorobenzene for 30 seconds at 2000 rpm using a Thinky Mixer. 50 wt% EPDM (5 wt% solution in chlorobenzene) is added to the mixture. The dispersion is mixed for 2 minutes at 200 rpm to obtain a homogeneous mixture. Chlorobenzene is added as needed to adjust the viscosity. The resulting dispersion is then coated onto a polypropylene film using a doctor blade and oven-cured at 80 °C for 2 hours followed by 12 hours at 120 °C. The film obtained is peeled from the substrate to produce Film 1. Compound 1(a) is converted into Compound 1 by contacting it with a KOH solution.(b) By extrusion. The pounded powder of Compound 2(a) is mixed with polyethylene or poly(styrene-co-butadiene) (hereinafter SBS) by extrusion at 110°C or 180°C to produce strands. Film formation is then carried out by extrusion through a die. Concentrations of 10, 50, 60, and 70 wt% of Compound 2 were tested. The composition of the films obtained is therefore as described in Table 1. Table 1. Composition of Films 2A to 2D, 3A, and 3B. Concentration of Compound 2 in KOH solution. An increase in the viscosity of the mixture was observed with increasing compound content, as shown in the diagram in Figure 3. Example 3 – Conductivity Measurements. Ionic conductivity measurements were performed on Film 1 as obtained in Example 2(a). The membrane was first activated with a 1M aqueous KOH solution for 24 hours, with the solution being degassed or not during activation. The through-plane conductivity was then measured with 0.1M and 1M KOH, and then on-plane with the hydrated film and 1M KOH. The film and electrolytes were exposed to air during all measurements. Under these conditions, Film 1 exhibited an on-plane conductivity of 73.7 mS / cm, while the through-plane measurement was not performed. In comparison, Sustanion membranes MC and Xion MCionic conductivities of 57.0 mS / cm and 102.2 mS / cm across the plane and 48.0 mS / cm and 28.2 mS / cm across the plane were obtained under the same conditions. Example 4 – NMR scattering measurements 1 H. Scattering measurements were performed on Film 1 as obtained in Example 2(a) by NMR 1 H on a 500 MHz NMR spectrometer using a Diff50 probe and an RF insert 1 H- 19An 8 mm double resonance F at 50°C was used. A stimulated echo with a sequence of longitudinal pulses delayed by eddy currents was employed for the measurement. The gradient pulse was 1.0 ms and the diffusion time was on the order of 100 ms. The gradient intensity was varied in 120 steps from 100 G / cm² to 2500 G / cm². As shown in Figure 4, the low mobility of protons in solid samples prevents the elimination of dipolar interactions between nuclei. This leads to significant line broadening and low resolution of the NMR spectra. 1H of solid compounds. As can be seen, only one broad resonance is observed in the spectrum of the dry film. However, an additional resonance at 4.5 ppm, corresponding to H2O, becomes visible in the hydrated film, confirming water absorption in the membrane. Short-duration magnetic field gradient pulses are introduced into the spin echo sequence to detect particle displacement in scattering NMR experiments. The intensity of the resulting signal (I) depends on the parameters of the applied gradients (B) and the self-scattering coefficient (D) of the molecules according to the following equation: ^^ = ^^0^^ −^^^^ The logarithmic plots of the signal attenuation as a function of B are shown in Figure 5, with the upper curve representing the dry film and the lower curve the hydrated film (points: experimental points, lines: fitting results). Two components with D = 2.7 × 10 -12 m 2 / s (probably OH-) and D = 1.9×10 -14 m 2 / s (main membrane) are identified in the dry film. In addition to these two components, two other diffusivities with D = 2.5×10 -10 m 2 / s (free water, i.e., water in large pores) and D = 2.1×10 -11 m 2 The bound water (i.e., water in direct contact with the membrane) is needed to accurately adjust the hydrated film data. NMR scattering measurements 1 H following the same protocol were also performed on Films 2A to 2C (wet) as obtained in Example 2(b) at temperatures of 25, 50, and 70°C. The results are presented in Table 2. For these experiments, the gradient intensity was modified in 128 steps from 100 G / cm² to 2300 G / cm². Table 2. Diffusion results for wet Films 2A to 2C. Film T (°C) Free water Bound water OH- Membrane The water on the membrane surface is labeled as “free water” for simplicity. However, it should be noted that the diffusion coefficient of pure water is 2.3 × 10⁻³ -9 m 2 s -1This is approximately twice as fast compared to the D observed in these experiments. This means that the water molecules interact with the membrane surface, and that this interaction prevents their diffusion. Two types of mobile particles are present in the tested samples: water inside the membrane pores, demonstrating a stronger interaction with the membrane than on the surface (bound water), and hydroxyl ions (OH-) incorporated into the membrane structure. The diffusivity of these molecules increases with increasing compound content, demonstrating the formation of a better anion transport network. Several modifications could be made to either of the embodiments described above without departing from the scope of the present invention as contemplated.References, patents or scientific literature documents referenced in this document are incorporated herein by reference in their entirety and for all purposes.

Claims

CLAIMS 1. A composition comprising a polymer and a compound comprising at least two cations derived from a quaternary ammonium compound or from an organic superbase such as amidine, guanidine, or phosphazene paired with at least two non-delocalized anions.

2. The composition of claim 1, wherein the cations are derived from an organic superbase such as amidine, guanidine, or phosphazene paired with at least two non-delocalized anions.

3. The composition of claim 1, wherein the compound is of Formula I: in which A is chosen from the groups C6-C 14 arylene and C5-C 14 possibly substituted heteroarylene, the C6-C groups 14 arylene and C5-C 14 heteroarylene being monocyclic or polycyclic, fused or not; R +is independently at each occurrence an organic group comprising a cation derived from a quaternary ammonium or an organic superbase amidine, guanidine, or phosphazene; X- is a non-delocalized anion; and n is an integer chosen from 2 to 6.

4. Composition of claim 3, wherein R + is an organic group comprising a cation derived from an organic superbase amidine, guanidine, or phosphazene.

5. Composition of claim 3 or 4, wherein at least one R + is a grouping of Formula II, III or IV: in , L 1 is a linear or branched C1-C6 alkylene group or is absent and A is bonded to N + by a covalent bond; R 2 is independently at each occurrence a linear or branched C1-12 alkyl group, substituted or unsubstituted, or at least two R 2together with their adjacent atom(s) form a saturated or partially unsaturated heterocycle with one or more rings and having from 5 to 12 members.

6. Composition of claim 5, wherein at least one R + is a grouping of Formula II.

7. Composition of claim 5, wherein at least one R + is a grouping of Formula III.

8. Composition of claim 5, wherein at least one R + is a grouping of Formula IV.

9. Composition of claim 5, wherein at least one R +comprises a cation selected from the cations of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP), tert-butylimino-tri(pyrrolidino)phosphorane (BTPP), and tert-butylimino-tris(dimethylamino)phosphorane (P1-t-Bu), preferably DBU.

10. Composition of claim 5 or 6, wherein at least one R + is chosen from Formulas II(a), II(b) or II(c): in which L 1 is as defined above, preferably of Formula II(a).

11. Composition of claim 5 or 7, wherein at least one R + is of Formula III(a): in which L 1 is as defined above.

12. Composition of claim 5 or 8, wherein at least one R + is chosen from Formulas IV(a), IV(b) or IV(c): in which L 1 is as defined above.

13. Composition of any one of claims 3 to 12, wherein at least one R + is an organic group comprising a cation derived from a quaternary ammonium, possibly linked to A by a group L 1 14. A composition of claim 13, wherein the cation derived from a quaternary ammonium is selected from aromatic or non-aromatic heterocyclic ammoniums having 5 to 10 ring atoms, the heterocycles optionally being substituted, the quaternary ammonium optionally being linked to A by an L group 1 15. Composition of any one of claims 5 to 14, wherein L 1 is a linear or branched C1-C6 alkylene group.

16. Composition of claim 15, wherein L 1is a methylene.

17. Composition of any one of claims 3 to 12, wherein A is a C6-C14arylene group, optionally substituted monocyclic or polycyclic, fused or unfused.

18. Composition of any one of claims 3 to 12, wherein A is a C6arylene group, optionally substituted (for example, by one or more methyl groups, etc.).

19. Composition of claim 18, wherein the compound is of Formula I(a), I(b), I(c), I(d), or I(e): + (R') + (R') 6X- + + in which, (R') + is the cation derived from a quaternary ammonium or an organic superbase amidine, guanidine or phosphazene and X- is as defined previously, for example (R') +is the cation derived from an organic superbase amidine, guanidine, or phosphazene.

20. Composition of any one of claims 1 to 19, wherein the non-delocalized anion is OH-, a halide ion, or a combination of at least two of these.

21. Composition of any one of claims 1 to 20, wherein the non-delocalized anion comprises OH-.

22. Composition of claim 1, wherein the compound is selected from Compounds 1 to 6:

23. A composition of claim 22, wherein the compound is selected from Compounds 1 and 2.

24. A composition of any one of claims 1 to 23, wherein the compound is present in said composition at a concentration of approximately 10% to approximately 95% by weight, or approximately 30% to approximately 90% by weight, or approximately 40% to approximately 90% by weight, or approximately 50% to approximately 80% by weight, inclusive of upper and lower bounds.

25. A composition of any one of claims 1 to 23, wherein the polymer is present in said composition at a concentration of at least 5% by weight, and preferably less than 50% by weight. 26.Composition of any one of claims 1 to 23, wherein the polymer is present in said composition at a concentration in the range of about 5% by weight to about 90% by weight, or from about 10% by weight to about 70% by weight, or from about 10% by weight to about 60% by weight. weight, or ranging from approximately 20% by weight to approximately 50% by weight, inclusive.

27. Composition of any one of claims 1 to 23, wherein the compound is present in said composition at a concentration of at least 50% by weight and the polymer is present in said composition at a concentration of at most 50% by weight.

28. Composition of any one of claims 1 to 27, wherein the polymer is linear or branched.

29. Composition of any one of claims 1 to 27, wherein the polymer is crosslinked.

30. Composition of any one of claims 1 to 27, wherein the polymer is non-crosslinked. 31.A composition of any one of claims 1 to 27, wherein the polymer is selected from polymers based on polyethylene, polypropylene, polybutadiene, polystyrene, fluoropolymer, substituted or unsubstituted polynorbornene, or a copolymer thereof, synthetic or natural rubber, optionally comprising at least one crosslinkable or crosslinked group.

32. A composition of claim 31, wherein the polymer is selected from fluoropolymers (for example, polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), and poly(vinylidene-co-hexafluoropropylene fluoride) (PVDF-HFP)).

33. Composition of claim 31, wherein the polymer is selected from polymers based on polyethylene, polypropylene, polybutadiene, polystyrene, substituted or unsubstituted polynorbornene, or a copolymer thereof (such as polyethylene, poly(ethylene-co-norbornene), poly(styrene-butadiene-styrene) or poly(styrene-co-butadiene) (SBS), etc.). 34.Composition of claim 31, wherein the polymer is a synthetic or natural rubber (such as natural rubbers, carboxylated nitrile rubber. (XNBR), hydrogenated nitrile rubber (HNBR), ethylene-propylene-diene polymer (EPDM), acrylonitrile-butadiene-styrene polymer (ABS), etc.).

35. Composition of any one of claims 1 to 27, wherein the polymer is a polyether-type polymer, optionally branched and / or crosslinked.

36. Composition of claim 35, wherein the polyether-type polymer is a polymer based on poly(ethylene oxide) (POE), poly(propylene oxide) (POP), or a combination or copolymer thereof, optionally branched and / or crosslinked.

37. A composition of any one of claims 1 to 27, wherein the polymer is a sequenced copolymer composed of at least one polyether segment and optionally at least one crosslinkable segment, the polyether segment being selected from homo- or copolymers having repeating units of formula -(CH2CH(R) 3 )O)y- in which R 3is chosen from a hydrogen atom, a C1-C10 alkyl group or a –(CH2-OR) group 4 R 5 ), R 4 is (CH2-CH2-O)m, R 5is selected from a hydrogen atom and a C1-C10 alkyl group, y is an integer selected from the range of 10 to 200,000; and m is an integer selected from the range of 0 to 10.

38. Composition of claim 37, wherein the crosslinkable segment of the copolymer is a polymer segment comprising at least one functional group crosslinkable multidimensionally by irradiation or heat treatment.

39. Composition of any one of claims 1 to 38, wherein the compound comprises at least one crosslinkable or crosslinked group, the crosslinking occurring between compounds or between the compound and the polymer.

40. Composition of any one of claims 1 to 39, further comprising an additional component selected from the group consisting of solvents, inorganic particles, plasticizers, and a combination of at least two of these. 41.Composition of claim 40, wherein the inorganic particles comprise glass particles, glass-ceramic particles, ceramic particles, or a combination of two or more of these.

42. Composition of claim 40, wherein the inorganic particles comprise a compound having a garnet-type structure, NASICON, LISICON, thio-LISICON, LIPON, perovskite, antiperovskite, argyrodite, or comprises a compound of the type MPS, MPSO, MPSX, MPSOX (where M is an alkali or alkaline earth metal, and X is F, Cl, Br, I or a combination of at least two of these) in crystalline, amorphous and / or glass-ceramic form, or a mixture of at least two of these.

43. Composition of claim 41, wherein the ceramic or glass-ceramic is an oxide-based, sulfide-based, oxysulfide-based ceramic, or a combination of at least two of these.

44. Composition of claim 43, wherein the sulfide-based ceramic is selected from Li10GeP2S12, Li6PS5Cl, Li2S–P2S5, Li7P3S11, Li9.54Si1.74P1.44S11.7Cl0.3, Li9.6P3S12 and Li3.25P0.95S4.

45. Composition of claim 44, wherein the sulfide-based ceramic is Li6PS5Cl. 46.

47. Composition of claim 40, wherein the inorganic particles comprise a filler additive selected from the group consisting of titanium dioxide (TiO2), alumina (Al2O3), and silicon dioxide (SiO2) particles or nanoparticles.

47. Composition of any one of claims 1 to 46, which is a solid or semi-solid composition, preferably a solid composition.

48. Membrane comprising the composition as defined in any one of claims 1 to 47 in the form of a solid film.

49. Membrane of claim 48, said membrane being an anion exchange membrane, for example, an anion exchange membrane for diffusion dialysis.

50. Membrane of claim 48, said membrane being an anion exchange membrane for use in an electrolyzer.

51. A membrane preparation method as defined in any one of claims 48 to 50, the method comprising the steps of: (i) combining the compound with the polymer and optionally an additional component as defined above to obtain a composite; and (ii) forming the membrane from the composite obtained in step (i).

52. A method of claim 51, wherein step (i) comprises mixing the compound with the polymer by extrusion.

53. A method of claim 51 or 52, wherein step (ii) is carried out by extrusion through a die. 54.A membrane preparation method as defined in any one of claims 48 to 50, the method comprising the steps of: (i) mixing the compound with the polymer and optionally an additional component as defined above in the presence of a solvent to obtain a composition; (ii) coating the composition obtained in step (i) onto a substrate; (iii) removing the solvent; and (iv) removing the substrate to produce the membrane.

55. A method of claim 54, wherein steps (ii) and (iii) are carried out sequentially, simultaneously, or partially overlapping in time with each other.

56. A method of claim 54 or 55, wherein the solvent is selected from an aromatic solvent or a halogenated solvent (such as toluene, chlorobenzene, and dichlorobenzene). 57.A method of any one of claims 54 to 56, wherein the substrate is chosen from polymer supports (such as polyethylene, polypropylene, etc.).

58. A method of any one of claims 54 to 57, wherein step (i) is carried out at a temperature in the range of approximately 20°C to approximately 50°C, or at room temperature.

59. A method of any one of claims 54 to 58, wherein the coating step is carried out by at least one squeegee coating method, a transfer interval coating method, a reverse transfer interval coating method, a printing method such as etching, or a slot coating method.

60. A method of claim 59, wherein the coating step is carried out by at least one squeegee coating method or a slot coating method.

61. A method of any one of claims 51 to 60, further comprising a step of treating the membrane with a metal hydroxide solution (such as KOH). 62.A method of any one of claims 51 to 61, further comprising a step of crosslinking the polymer, the compound, or both, for example in the membrane.

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