WO1998029388A1 - Sels d'amides perfluores, et leurs utilisations comme materiaux a conduction ionique - Google Patents

Sels d'amides perfluores, et leurs utilisations comme materiaux a conduction ionique Download PDF

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Publication number
WO1998029388A1
WO1998029388A1 PCT/CA1997/001013 CA9701013W WO9829388A1 WO 1998029388 A1 WO1998029388 A1 WO 1998029388A1 CA 9701013 W CA9701013 W CA 9701013W WO 9829388 A1 WO9829388 A1 WO 9829388A1
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PCT/CA1997/001013
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English (en)
French (fr)
Inventor
Christophe Michot
Michel Armand
Michel Gauthier
Yves Choquette
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Hydro Quebec
Centre National de la Recherche Scientifique CNRS
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Hydro Quebec
Centre National de la Recherche Scientifique CNRS
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25678955&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1998029388(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from CA002194127A external-priority patent/CA2194127A1/fr
Priority claimed from CA002199231A external-priority patent/CA2199231A1/fr
Priority to CA2248303A priority Critical patent/CA2248303C/fr
Application filed by Hydro Quebec, Centre National de la Recherche Scientifique CNRS filed Critical Hydro Quebec
Priority to JP52951898A priority patent/JP4823401B2/ja
Priority to US09/125,797 priority patent/US6319428B1/en
Publication of WO1998029388A1 publication Critical patent/WO1998029388A1/fr
Anticipated expiration legal-status Critical
Priority to US10/253,035 priority patent/US20030052310A1/en
Priority to US10/789,453 priority patent/US20050074668A1/en
Priority to US11/867,898 priority patent/US20240253023A1/en
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Definitions

  • the present invention relates to ionic compounds in which the anionic charge is delocalized, and their uses.
  • the inventors have found that the excellent solubility and dissociation properties of the ionic groups -S0 2 -N-S0 2 - were preserved when a single sulfonated group had fluorine atoms on atoms adjacent to the sulfur atom, leaving an extremely wide choice of functional molecules.
  • the Hammett parameter ⁇ * of a group -S0 2 - linked to a non-perfluorinated group is 3.5 and 4.55 for a group CF 3 S0 2 -.
  • the present invention therefore relates to a family of ionic compounds having good solubility and good dissociation, without the need to resort to complex modifications of the starting molecule.
  • the precursors of the molecules of the invention are in the form of derivatives of sulfonic acids or of amino groups on the one hand, and derivatives of the perfluorosulfonyl type on the other hand, which are for the most part industrial products and / or easily accessible. It should be noted in in addition to reducing the perfluorinated fraction in the compounds of the invention makes it possible to reduce the production costs of said compounds and consequently the cost of the applications which are made of them.
  • a compound of the present invention is an ionic compound consisting of an amide or one of its salts, comprising an anionic part associated with at least one cationic part M + m in sufficient number to ensure the electronic neutrality of the whole. It is characterized in that M m + is a hydroxonium, a nitrosonium N0 + , an ammonium -NH 4 + , a metal cation having the valence m, an organic cation having the valence m or an organometallic cation having the valence m, and in that the anionic part corresponds to the formula R F -SO x -lsrz, in which: the group -SO x - represents a sulphonyl group -SO 2 - or a sulfinyl group -SO-; - R F is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thi
  • R F is R A CF 2 -, R A CF 2 CF 2 -, R A CF 2 CF (CF 3 ) - , CF3C (R A ) F- or a perhaloalkyl radical having from 1 to 2 carbon atoms which does not promote phase separation due to the aggregation of the fluorinated segments.
  • the cation can be a metal cation chosen from alkali metal cations, alkaline earth metal cations, transition metal cations, trivalent metal cations, rare earth cations.
  • a metal cation chosen from alkali metal cations, alkaline earth metal cations, transition metal cations, trivalent metal cations, rare earth cations.
  • the cation can also be an organometallic cation, in particular a metallocenium.
  • organometallic cation in particular a metallocenium.
  • organometallic cation can be part of a polymer chain.
  • the compounds of the invention have an organic cation chosen from the group consisting of the cations R 3 0 + (oxonium), NR 4 + (ammonium), RC (NHR 2 ) 2 + (amidinium), C (NHR 2 ) 3 + (guanidinium), C 5 R 6 N + ( pyridinium), C 3 RN 2 + (imidazolium), C 3 R 7 N 2 + (imidazolinium), C 2 R 4 N 3 + (triazolium), SR 3 + (sulfonium), PR + (phosphonium), IR 2 + (iodonium), (C 6 B ) 3 C + (carbonium).
  • the radicals R can all be identical.
  • a radical R can be an H or else it is chosen from the following radicals: alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl, sila-alkyl radicals , sila- alkenyls, aryls, arylalkyls, alkyl-aryls, alkenyl-aryls, dialkylamino and dialkylazo; cyclic or heterocyclic radicals optionally comprising at least one side chain comprising heteroatoms such as nitrogen, oxygen, sulfur; cyclic or heterocyclic radicals optionally comprising heteroatoms in the aromatic nucleus; groups comprising several aromatic or heterocyclic rings, condensed or not, optionally containing at least one nitrogen, oxygen, sulfur or phosphorus atom.
  • an onium cation carries at least two radicals R different from H, these radicals can together form an aromatic ring or not, possibly including the center carrying the cationic charge.
  • the cationic part of a compound of the invention when it is an onium cation, it can be either in the form of an independent cationic group which is only linked to the anionic part. by the ionic bond between the positive charge of the cation and the negative charge of the anionic part.
  • the cationic part can be part of a repeating unit of a polymer.
  • An onium cation can also be part of the radical Z or of the radical R D carried by the anion center.
  • a compound of the invention constitutes a zwitterion.
  • the cation of a compound of the invention is an onium cation, it can be chosen so as to introduce into the compound substituents making it possible to confer on said compound specific properties.
  • the cation M + can be a cationic heterocycle of aromatic character, comprising at least one alkyl nitrogen atom in the ring.
  • an imidazolium, a triazolium, a pyridinium, a 4-dimethylamino-pyridinium said cations optionally carrying a substituent on the carbon atoms of the ring.
  • these cations those which give an ionic compound according to the invention whose melting point is less than 150 ° C. are particularly preferred.
  • a particularly preferred proton-conducting material comprises a compound according to the invention in which the cation is formed by the addition of a proton on the nitrogen of an imidazoline, an imidazole or a triazole, as well as the nitrogenous base. corresponding in a proportion of 0.5 to 10 in molar ratio.
  • the cation is a diaryliodonium cation, a dialkylaryliodonium cation, a triarylsulfonium cation, a trialkylaryl sulfonium cation, or a substituted or unsubstituted phenacyl-dialkyl sulfonium cation.
  • the above-mentioned cations can be part of a polymer chain.
  • the cation M of a compound of the invention can incorporate a group 2, 2 '[Azobis (2-2' - imidazolinio-2-yl) propane] + or 2, 2 '- Azobis (2-amidiniopropane) + .
  • the compound of the invention is then capable of liberating, under the action of heat or ionizing radiation, radicals which make it possible to initiate polymerization reactions, crosslinking or, in general, reactions chemicals involving free radicals.
  • these compounds are easily soluble in polymeric and monomeric organic solvents even of low polarity, unlike derivatives of Cl " type anions usually associated with this type of compound.
  • R F is a fluorine atom or a perhalogenated alkyl radical preferably having from 1 to 12 carbon atoms, or a perhalogenated alkylaryl radical having preferably 6 to 9 carbon atoms.
  • the perhalogenated alkyl radical can be a linear or branched radical. Mention may in particular be made of the radicals in which the carbon atom which will be in position ⁇ relative to the group -S0 X - carries at least one fluorine atom.
  • R A represents an organic radical not perhalogenated, an alkyl group, an aryl group, an alkylaryl or arylalkyl group; a group comprising at least one ethylenic unsaturation and / or a condensable group and / or a dissociable group; a mesomorphic group; a chromophore group; a self-doped electronic conductive polymer; a hydrolyzable alkoxysilane; a polymer chain carrying grafts having a carbonyl group, a sulfonyl group, a thionyl group or a phosphonyl group; a group capable of trapping free radicals such as a hindered phenol or a quinone;
  • a particular family of compounds of the invention is that in which Z represents a group R D Y-.
  • R D is chosen from alkyl, alkenyl, oxa-alkyl, oxa- alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl or thia-alkenyl having from 1 to 24 carbon atoms, or from aryl, arylalkyl, alkylaryl or alkenylaryl radicals having from 5 to 24 carbon atoms.
  • R D is chosen from alkyl or alkenyl radicals having from 1 to 12 carbon atoms and optionally comprising at least one 0, N or S heteroatom in the main chain or in a side chain, and / or optionally carrying a hydroxy group, a carbonyl group, an amino group or a carboxyl group.
  • a substituent R D can be a polymer radical, for example an oligo (oxyalkylene) radical.
  • the compound of the invention is then in the form of a polymer carrying an ionic group - [YN-S0 X -R F ] ⁇ , M + .
  • R D can be a repeating unit of a polymer, for example an oxyalkylene unit or a styrene unit.
  • the compound of the invention is then in the form of a polymer in which at least part of the repeating units carry a side group to which is attached an ionic group
  • a particular category of compounds according to the invention comprises the compounds in which the substituent R D has at least one anionic ionophore group and / or at least one cationic ionophore group.
  • the anionic group can for example be a carboxylate function (-C0 2 ⁇ ), a sulfonate function (-S0 3 ⁇ ), a function sulfonimide (-S0 2 NS0 2 -) or a sulfonamide function (-S0 2 N-).
  • the cationic ionophore group can for example be an iodonium, sulfonium, oxonium, ammonium, amidinium, guanidiniu, pyridinium, imidazolium, imidazolinium, triazolium, phosphonium or carbonium group.
  • the cationic ionophore group can fully or partially play the role of the cation M.
  • R D comprises at least one ethylenic unsaturation and / or a condensable group and / or a group which can be dissociated thermally, photochemically or by ionic dissociation
  • the compounds of the invention are reactive compounds which can be subjected to polymerizations , crosslinks or condensations, possibly with other monomers. They can also be used to fix ionophoric groups on polymers carrying the appropriate reactive function.
  • a substituent R D can be a mesomorphic group or a chromophore group or a self-doped electronic conductive polymer or a hydrolysable alkoxysilane.
  • a substituent R D may contain a group capable of trapping free radicals, for example a hindered phenol or a quinone.
  • a substituent R D can also comprise a dissociating dipole, for example an amide function, a sulfonamide function or a nitrile function.
  • a substituent R D can also comprise a redox couple, for example a disulfide group, a thioamide group, a ferrocene group, a phenothiazine group, a bis (dialkylaminoaryl) group, a nitroxide group or an aromatic group.
  • a redox couple for example a disulfide group, a thioamide group, a ferrocene group, a phenothiazine group, a bis (dialkylaminoaryl) group, a nitroxide group or an aromatic group.
  • a substituent R D can also comprise a complexing ligand, or an optically active group.
  • Another category of compounds of the invention includes compounds in which R D -Y- represents an amino acid, or an optically or biologically active polypeptide.
  • a compound according to the invention comprises a substituent R D which represents a radical having a valence v greater than two, itself comprising at least one group R F -S (0) X -NY-. In this case, the negative charges present on the anionic part of the compound of the invention must be compensated for by the appropriate number of cations or cationic ionophoric groups M.
  • a compound of the present invention corresponds to the formula R F -S (O) X -NZ, in which Z is an electron-withdrawing group not bound to nitrogen carrying the negative charge by a group Y
  • Z can also be a radical C n F 2n + 1 CH 2 -, n being an integer from 1 to 8, or among heterocycles, in particular those derived from pyridine, pyrazine, pyrimidine, oxadiazole, thiadiazole, fluorinated or not.
  • Z can also represent a repeating unit of a polymer.
  • the compound of the invention is then in the form of a polymer in which at least part of the repeating units bear a side group to which is attached an ionic group - [(N-S0 X -R F ) ⁇ r M + ].
  • a polymer comprising one of the following recurring units: or a polyzwitterion of self-doped polyaniline conductive polymer whose recurring unit is:
  • the compounds of the present invention can be obtained by a process in which a compound R F SO x -L is reacted with a compound [ANZ] n ⁇ m nM m + , R F , x, M and Z being as defined above , L representing an electronegative leaving group such as a halogen, an N-imidazoyl radical, an N-triazoyl radical, an R F SO x + ⁇ - radical and A representing a cation M m + , a trialkylsilyl group, a trialkyl germanyl group, a trialkylstannyl group or a tertioalkyl group, in which the alkyl substituents have from 1 to 6 carbon atoms.
  • a fluorosulfonyl fluoride with a cyanamide di salt according to the following reaction scheme:
  • the base can be chosen from alkylamines (for example triethylamine, di-isopropylamine, quinuclidine), 1,4-diazobicyclo [2, 2, 2] octane (DABCO); pyridines (for example pyridine, alkylpryidines, dialkylaminopyridines); imidazoles (for example N-alkylimidazoles, imidazo [1, la] pyridine); amidines (for example, 1,5-diazabicyclo- [4,3,0] non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] undec-7-ene (DBU) ); guanidines (for example tetramethyl guanidine, 1,3,4,7,8-hexahydro-1-methyl-2H-pyrimido [1, 2-a] pyrimidine (HPP).
  • alkylamines for example triethylamine, di-isopropylamine, qui
  • R 1 independently represent an alkyl radical, an aryl radical or a dialkylamino radical.
  • the cation of a compound obtained according to either of the methods described above can be replaced by the conventional cation exchange methods, either by precipitation or selective extractions, or by the use of resins ion exchangers.
  • the substituent R D of a compound of the invention can be modified by known reactions.
  • an R D substituent which includes an allyl group can be transformed by reaction with a peroxide to obtain an epoxidized R D substituent.
  • An -NHR group can be transformed into a vinyl ester group by reaction with a strong base such as potassium tert-butoxide, then with vinyl chloroformate.
  • the methods for carrying out these modifications and others are within the reach of those skilled in the art.
  • the functions carried by the radicals R A and Z which could interfere with the reactions allowing the preparation of the compounds of the invention can be temporarily protected by known techniques.
  • an amino function can be protected by a t-BOC (tert-butoxycarbonyl) group, stable in the presence of bases T but easily eliminated by treatment in an acid medium.
  • the ionic compounds of the present invention comprise at least one ionophore group to which are attached substituents which can be very varied. Given the large choice possible for the substituents, the compounds of the invention make it possible to induce ionic conduction properties in most organic, liquid or polymeric media having even a low polarity.
  • the applications are important in the field of electrochemistry, in particular energy storage in primary or secondary generators, in supercapacitors, in fuel cells and in light emitting diodes.
  • the compatibility of the ionic compounds of the invention with polymers or organic liquids makes it possible to induce marked antistatic properties, even when the content of ionic compound is extremely low.
  • the compounds of the invention which are polymers, as well as the polymer compounds obtained from compounds of the invention having the property of polymerizing or of copolymerizing, have the properties listed above with the advantage of have a stationary anionic charge. This is why another object of the present invention consists of an ionically conductive material consisting of an ionic compound of the present invention in solution in a solvent.
  • the ionic compound used for the preparation of an ionically conductive material is chosen from compounds whose cation is ammonium, or a cation derived from a metal, in particular lithium or potassium , zinc, calcium, metals of rare earths, or an organic cation, such as a substituted ammonium, an imidazolium, a triazolium, a pyridinium, a 4-dimethylamino-pyridinium, said cations optionally carrying a substituent on the carbon atoms of the ring.
  • the ionically conductive material thus obtained has high conductivity and solubility in solvents, due to the weak interactions between the positive charge and the negative charge.
  • Ionically conducting materials which incorporate a compound of the invention in which R F is a fluorine atom or a perhalogenated alkyl radical having from 1 to 12 carbon atoms, or a perhalogenated alkylaryl radical having from 6 to 9 carbon atoms are interesting since the weak interactions between the fluorine atoms in the chain lead to high solubilities and conductivity, even in the case where the rest of the molecule contains groups tending to give strong interactions such as conjugated aromatic radicals or the zwitterions.
  • R F is chosen from the radicals R A CF 2 -, R A CF 2 CF 2 -, R A CF 2 CF (CF 3 ) - or CFsC (R A ) F - makes it possible to very precisely adapt the properties of the ionically conductive material by appropriately choosing the substituent R A. In particular, they make it possible to benefit, with a reduced number of fluorine atoms, from the dissociation and solubility properties specific to the anionic charges of perfluorinated systems. These groups are easily accessible from industrial products such as tetrafluoroethylene or tetrafluoropropylene. The reduced amount of fluorine makes these compounds less sensitive to reduction by very electropositive metals such as aluminum, magnesium or especially lithium.
  • the properties of the ionically conductive material can also be adapted by the choice of the substituent R D.
  • R A or R D of an alkyl group, of an aryl group, of an alkylaryl group or of an arylalkyl group makes it possible to induce in the ionically conductive material properties of mesogenic type, in particular alkyl groups of 6 to 20 carbon atoms, aryl-alkyl groups, in particular those containing the biphenyl entity which form liquid crystal type phases.
  • Conduction properties in liquid crystal, nematic, cholesteric or discotic type phases are advantageous for applications relating to optical displays or for reducing the mobility of anions in electrolytes, in particular in polymer electrolytes, without affecting the mobility of cations. This particularity is important for applications in electrochemical generators, in particular those involving lithium cations.
  • the substituent R A is a mesomorphic group or a group comprising at least one ethylenic unsaturation and / or a condensable group and / or a group dissociable by thermal route, by photochemical route or by ionic dissociation, or when R D is a substituent containing one of these groups
  • the ionically conductive material readily forms polymers or copolymers which are polyelectrolytes, either intrinsic when the polymer carries solvating groups, or by addition of a polar solvent of the type liquid or polymer, or by mixing with such a solvent.
  • These products have a conductivity only due to cations, which is a very useful property in applications of the electrochemical generator type. In low molar fraction in a copolymer, they induce stable antistatic properties which are not very dependent on humidity and promote the fixation of cationic dyes, this property being useful for textile fibers and dye lasers.
  • R A or R D which is a self-doped electronic conductive polymer, improves the stability of the ionically conductive material with respect to external agents.
  • the conductivity is stable over time even at high temperatures. In contact with metals, these materials give very low interface resistances and in particular protect ferrous metals or aluminum from corrosion.
  • the ion-conducting material can form stable polymers by simple hydrolysis-condensation mechanism in the presence of water, thus making it possible to treat the surfaces of oxides, of silica , silicates, in particular glass, to induce surface conduction properties, antistatic properties, or to promote the adhesion of polar polymers.
  • the substituent R A or R D is a group comprising a free radical trap such as Hindered phenol, or a quinone
  • the ionically conductive material has the following advantages and properties: it acts as an antioxidant which does not exhibit volatility and is compatible with polar monomers and polymers, to which it also confers antistatic properties.
  • the ionically conductive material has an improved conductivity in mediums of low and medium polarity, in particular in solvating polymers, this which minimizes or even eliminates the addition of solvents or volatile plasticizers.
  • R A or R D which contains a redox couple such as a disulfide, a thioamide, a ferrocene, a phenothiazine, a bis (dialkylaminoaryl) group, a nitroxide, an aromatic imide, makes it possible to induce in the ionically conductive material redox shuttle properties useful as a protective element and charge equalization of electrochemical generators, in photoelectrochemical systems, in particular of conversion of light into electricity, in light modulation systems electrochromic type.
  • a redox couple such as a disulfide, a thioamide, a ferrocene, a phenothiazine, a bis (dialkylaminoaryl) group, a nitroxide, an aromatic imide
  • R A or R D which is a complexing ligand in an ionically conductive material makes it possible to chelate the metal cations, in particular those which have a high charge.
  • the ionic compound of the invention can give, by polycondensation, a polymer or a copolymer and the ionically conductive material which contains such a polymer or copolymer has polyelectrolyte properties.
  • R D is chosen from aryl, arylalkyl, alkylaryl or alkenylaryl radicals, in which the side chains and / or the aromatic rings comprise heteroatoms such that nitrogen, oxygen, sulfur, improves dissociation and increases the possibility of forming complexes according to the position of the heteroatom (pyridine) or of giving by duplicative oxidation of conjugated polymers or copolymers (pyrrole, thiophene).
  • the ionically conductive material contains a compound of the invention in which R D represents a recurring unit of a polymer chain, the material constitutes a polyelectrolyte.
  • An ion-conducting material which contains such a compound is therefore particularly suitable as an electrolyte for a fuel cell.
  • An ionically conductive material of the present invention comprises an ionic compound of the invention in solution in a solvent.
  • the solvent can be an aprotic liquid solvent, a polar polymer or a mixture thereof.
  • the aprotic liquid solvent is chosen, for example, from linear ethers and cyclic ethers, esters, nitriles, nitro derivatives, amides, sulfones, sulfolanes, alkyl sulfamides and partially halogenated hydrocarbons.
  • Particularly preferred solvents are diethyl ether, dimethoxyethane, glyme, tetrahydrofuran, dioxane, dimethyltetrahydrofuran, methyl or ethyl formate, propylene or ethylene carbonate, alkyl carbonates (in particular alkyl dimethyl carbonate, diethyl carbonate and methylpropyl carbonate), butyrolactones, acetonitrile, benzonitrile, nitromethane, nitrobenzene, dimethylformamide, diethyl-amide, N-methylpyrrolidone, dimethylsulfone, tetramethylene sulfone and tetraalkylsulfonamides having 5 to 10 carbon atoms.
  • the polar polymer can be chosen from solvating polymers, crosslinked or not, bearing or not grafted ionic groups.
  • a solvating polymer is a polymer which comprises solvating units containing at least one heteroatom chosen from sulfur, oxygen, nitrogen and fluorine.
  • solvating polymers mention may be made of polyethers of linear, comb or block structure, which may or may not form a network, based on poly (ethylene oxide), or the copolymers containing the oxide motif d ethylene or propylene oxide or allylglycidylether, polyphosphazenes, crosslinked networks based on polyethylene glycol crosslinked by isocyanates or networks obtained by polycondensation and carrying groups which allow the incorporation of crosslinkable groups.
  • An ion-conducting material of the present invention can simultaneously comprise an aprotic liquid solvent chosen from the aprotic liquid solvents mentioned above and a polar polymer solvent comprising units containing at least one heteroatom chosen from sulfur, nitrogen, oxygen and fluorine. It can comprise from 2 to 98% of liquid solvent.
  • a polar polymer mention may be made of polymers which mainly contain units derived from acrylonitrile, vinylidene fluoride, N-vinylpyrrolidone or methyl methacrylate.
  • the proportion of aprotic liquid in the solvent can vary from 2% (corresponding to a plasticized solvent) to 98% (corresponding to a gelled solvent).
  • An ion-conducting material of the present invention can also contain a salt conventionally used in the prior art for the preparation of an ion-conducting material.
  • a salt chosen from perfluoroalkanesulfonates, bis (perfluoroalkylsulfonyl) imides, bis (perfluoroalkylsulfonyl) methanes and tris (perfluoroalkylsulfonyl) is particularly preferred. ) methane.
  • an ion-conducting material of the invention can also contain the additives conventionally used in this type of material, and in particular mineral or organic fillers in the form of powder or fibers.
  • An ionically conductive material of the invention can be used as an electrolyte in an electrochemical generator.
  • Another subject of the present invention is therefore an electrochemical generator comprising a negative electrode and a positive electrode separated by an electrolyte, characterized in that the electrolyte is an ionically conductive material as defined above.
  • such a generator comprises a negative electrode constituted by metallic lithium, or by one of its alloys, optionally in the form of a nanometric dispersion in lithium oxide, or by a double nitride.
  • the collector of the positive electrode is preferably made of aluminum.
  • An ionically conductive material of the present invention can also be used in a supercapacitor.
  • Another object of the present invention is therefore a supercapacitor using at least one carbon electrode with a high specific surface, or an electrode containing a redox polymer, in which the electrolyte is an ionically conductive material as defined above.
  • An ionically conductive material of the present invention can also be used for the p or n doping of an electronically conductive polymer and this use constitutes another object of the present invention.
  • an ionically conductive material of the present invention can be used as an electrolyte in an electrochromic device.
  • Another object of the present invention is an electrochromic device in which the electrolyte is an ionically conductive material according to the invention.
  • the present invention therefore also relates to the use of ionic compounds as photoinitiators sources of Brnsted acids catalysts for polymerization or crosslinking of monomers or prepolymers capable of reacting cationically, or as catalysts for the modification of polymers.
  • the process for the polymerization or crosslinking of monomers or prepolymers capable of reacting cationically is characterized in that a compound of the invention is used as photoinitiator source of acid catalyzing the polymerization reaction.
  • a compound of the invention is used as photoinitiator source of acid catalyzing the polymerization reaction.
  • the choice of the substituent R F on the one hand, of the substituents R D or Z on the other hand, is carried out so as to increase the solubility of said compound in the solvents used for the reaction of the monomers or prepolymers, and according to the properties desired for the final polymer.
  • the choice of unsubstituted alkyl radicals gives solubility in slightly polar media.
  • the choice of radicals comprising an oxa group or a sulfone will give a solubility in polar media.
  • the radicals including a sulfoxide group, a sulfone group, a phosphine oxide group, a phosphonate group, obtained respectively by addition of oxygen to the atoms sulfur or phosphorus, can give the obtained polymer improved properties with regard to adhesion, gloss, resistance to oxidation or UV.
  • the monomers and prepolymers which can be polymerized or crosslinked using the photoinitiators of the present invention are those which can undergo cationic polymerization.
  • monomers which comprise a cyclic ether function, a cyclic thioether function or a cyclic amine function, vinyl compounds (more particularly vinyl ethers), oxazolines, lactones and lactams.
  • monomers of the cyclic ether or thioether type there may be mentioned ethylene oxide, propylene oxide, oxetane, epichlorohydrin, tetrahydrofuran, styrene oxide, cyclohexene oxide, vinylcyclohexene oxide, glycidol, butylene oxide, octylene oxide, glycidyl ethers and esters (e.g.
  • glycidyl methacrylate or acrylate phenyl glycidyl ether, bisphenol A diglycidyl ether or its fluorinated derivatives
  • cyclic acetals having 4 to 15 carbon atoms for example dioxolane, 1,3-dioxane, 1,3-dioxepane
  • spiro-bicyclo dioxolanes for example dioxolane, 1,3-dioxane, 1,3-dioxepane
  • vinyl ethers constitute a very important family of monomers sensitive in cationic polymerization.
  • ethyl vinyl ether propyl vinyl ether, isobutyl vinyl ether, octadecyl vinyl ether, ethylene glycol monovinyl ether, diethylene glycol divinyl ether, butanediol monovinyl ether, butanediol divinyl ether, hexanediol divinyl ether, ethylene glycol butyl vinyl ether, triethylene glycol methyl vinyl ether, cyclohexanedimethano monovinyl ether, cyclohexanedimethanol divinyl ether, 2-ethylhexyl vinyl ether, poly-THF-divinyl ether having a mass between 150 and 5000, diethylene glycol monovinyl ether trivinyl ether, aminopropyl vinyl ether, 2-diethyl vinyl ether,
  • vinyl compounds mention may be made, for example, of 1, 1-dialkylethylenes (for example isobutene), vinyl aromatic monomers (for example styrene, ⁇ -alkylstyrene, in particular ⁇ -methylstyrene, 4-vinylanisole, acenaphthene), N-vinylic compounds (for example N-vinylpyrolidone or N-vinyl sulfonamides).
  • 1, 1-dialkylethylenes for example isobutene
  • vinyl aromatic monomers for example styrene, ⁇ -alkylstyrene, in particular ⁇ -methylstyrene, 4-vinylanisole, acenaphthene
  • N-vinylic compounds for example N-vinylpyrolidone or N-vinyl sulfonamides.
  • epoxy groups are carried by an aliphatic chain, an aromatic chain or a heterocyclic chain
  • the glycidyl ethers of bisphenol A ethoxylated with 3 to 15 units of ethylene oxide for example the siloxanes having side groups of the epoxycyclohexene-ethyl type obtained by hydrosilylation of the dialkyl, alkylaryl or diaryl siloxane copolymers with methyl hydrogenosiloxane in the presence of vinylcyclohexene oxide, the condensation products of the sol-gel type obtained with starting from triethoxy or trimethoxy silapropylcyclohexene oxide, the urethanes incorporating the reaction products of butanediol monovinylether and an alcohol of functionality greater than or equal to 2 on an aliphatic or aromatic di or tri isocyanate.
  • the polymerization process according to the invention consists in mixing at least one monomer or prepolymer capable of polymerizing by the cationic and at least one ionic compound of the invention, and subjecting the mixture obtained to actinic radiation or ⁇ radiation.
  • the reaction mixture is subjected to radiation after having been formed in the form of a thin layer having a thickness less than 5 mm, preferably in the form of a thin film having a thickness less than or equal to 500 ⁇ m.
  • the reaction time depends on the thickness of the sample and the power of the source at the active wavelength ⁇ . It is defined by the speed of travel in front of the source, which is between 300 m / min and 1 cm / min. Layers of final material having a thickness greater than 5 mm can be obtained by repeating several times the operation of spreading a layer and treating it with radiation.
  • the amount of photoinitiator used is between 0.01 and 15% by weight relative to the weight of monomer or prepolymer, preferably between 0.1 and 5% by weight.
  • An ionic compound of the present invention can be used as photoinitiator in the absence of solvent, in particular when it is desired to polymerize liquid monomers in which the ionic compound used as photoinitiator is soluble or easily dispersible. This form of use is particularly interesting, because it eliminates the problems associated with solvents (toxicity, flammability).
  • An ionic compound of the present invention can also be used as a photoinitiator in the form of a homogeneous solution in a solvent inert to the polymerization, ready to use and easily dispersible, in particular particularly in the case where the medium to be polymerized or crosslinked has a high viscosity.
  • an inert solvent mention may be made of volatile solvents, such as acetone, methyl ethyl ketone and acetonitrile. These solvents will simply serve to dilute the products to be polymerized or crosslinked (to make them less viscous, especially when it is a prepolymer). They will be removed after polymerization or crosslinking by drying. Mention may also be made of non-volatile solvents. A non-volatile solvent also serves to dilute the products which it is desired to polymerize or crosslink, and to dissolve the salt A + X " of the invention used as photoinitiator, but it will remain in the material formed and it thus acts as a plasticizer.
  • volatile solvents such as acetone, methyl ethyl ketone and acetonitrile.
  • propylene carbonate By way of example, mention may be made of propylene carbonate, ⁇ -butyrolactone, ether-esters of mono-, di-, tri-ethylene or propylene glycols, ether-alcohols of mono-, di-, tri- ethylene or propylene glycols, plasticizers such as esters of phthalic acid or citric acid.
  • a reactive compound with respect to polymerization is used as solvent or diluent, which is a compound of low molecular mass and of low viscosity which will play both role of polymerizable monomer and the role of solvent or diluent for more viscous monomers or prepolymers used together.
  • solvent or diluent a compound of low molecular mass and of low viscosity which will play both role of polymerizable monomer and the role of solvent or diluent for more viscous monomers or prepolymers used together.
  • a reactive solvent can be chosen from mono and di vinyl ethers of mono-, di-, tri-, tetra-ethylene and propylene glycols, N-methylpyrolidone, 2-propenyl ether of propylene carbonate sold. for example under the name PEPC by the company ISP, New Jersey, United States.
  • the radiation can be chosen from ultraviolet radiation, visible radiation, X-rays, ⁇ rays and ⁇ radiation.
  • photoinitiators of the invention When using ultraviolet light as actinic radiation, it may be advantageous to add to the photoinitiators of the invention photosensitizers intended to allow efficient photolysis with wavelengths less energetic than those corresponding to the maximum absorption of the photoinitiator, such as those emitted by industrial devices, ( ⁇ ⁇ 300 nm for mercury vapor lamps in particular).
  • Such additives are known, and by way of nonlimiting examples, mention may be made of anthracene, diphenyl-9, 10-anthracene, perylene, phenothiazine, tetracene, xanthone, thioxanthone, acetophenone, benzophenone, 1, 3, 5-triaryl-2-pyrazolines and their derivatives, in particular the derivatives of substitution on aromatic rings by alkyl, oxa— or aza — alkyl radicals allowing among other things to change the wavelength absorption.
  • Isopropylthioxantone is an example of a preferred photosensitizer when an iodonium salt according to the invention is used as the photoinitiator.
  • ultraviolet radiation is particularly preferred.
  • photoinitiators are generally directly sensitive to UV rays and photosensitizers are more effective the smaller the energy difference ( ⁇ ).
  • the ionic compounds of the invention can also be used in combination with initiators of the radical type generated thermally or by the action of actinic radiation. It is thus possible to polymerize or crosslink mixtures of monomers or prepolymers containing functions whose polymerization modes are different, for example monomers or prepolymers polymerizing by the radical route and monomers or prepolymers polymerizing by the cationic route.
  • the vinyl ethers are not or are not very active by radical initiation. It is therefore possible, in a reaction mixture containing a photoinitiator according to the invention, a radical initiator, at least one monomer of the vinyl ether type and at least one monomer comprising non-activated double bonds such as those of the allylic groups, to carry out separate polymerization of each type of monomer.
  • examples include initiators the following commercial products: Irgacure ® 184, Irgacure ® 651, Irgacure 261®, Quantacure DMB®, Quantacure ITX®.
  • a mixture of a heat-dissociable radical initiator and a cationic photoinitiator according to the invention makes it possible to carry out sequential polymerizations or cross-linkings, first under the action of heat, then under the action of a actinic radiation.
  • Radical initiators can for example be Irgacure® 651 making it possible to initiate radical polymerizations at wavelengths of 365 nm.
  • the invention also relates to the use of the ionic compounds of the invention for the chemical amplification reactions of photoresists for microlithography.
  • a film of a material comprising a polymer and an ionic compound of the invention is subjected to irradiation.
  • the irradiation causes the formation of the acid by replacing the cation M with a proton, which catalyzes the decomposition or transformation of the polymer.
  • the monomers formed or the transformed polymer are eliminated and an image of the unexposed parts remains.
  • a compound of the invention which is in the form of a polymer essentially consisting of styrenyl repeating units carrying an ionic substituent R F -S0 X -N ⁇ -.
  • polymers containing ester units or aryl ether units of tertioalkyl for example poly (phthalaldehydes), polymers of bisphenol A and of a diacid, polytertiobutoxycarbonyl oxy- styrene, polytertiobutoxy- ⁇ -methyl styrene, polyditertiobutylfumarate-co-allyltrimethylsilane and polyacrylates of a tertiary alcohol, in particular tertiary butyl polyacrylate.
  • polymers containing ester units or aryl ether units of tertioalkyl for example poly (phthalaldehydes), polymers of bisphenol A and of a diacid, polytertiobutoxycarbonyl oxy- styrene, polytertiobutoxy- ⁇ -methyl styrene, polyditertiobutylfumarate-co-allyltrimethylsilane and polyacrylates of
  • the ionic compounds of the present invention which exhibit high thermal stability, offer many advantages over the salts known from the prior art. They have priming and propagation speeds comparable to or greater than those obtained using coordination anions of the PF 6 ⁇ , AsF 6 ⁇ and especially SbF 6 ⁇ type .
  • the diffusion coefficient of the anion R F -SO x - N " - is greater than that of hexafluorometallate anions or tetrafluoroborate anions or phenylborate anions.
  • the ion pairs exhibit a very strong dissociation, which allows the expression of the intrinsic catalytic properties of the cation M m + , whose active orbitals are easily exposed to the reaction substrates, this in various backgrounds. Most of the important reactions of organic chemistry can thus be carried out under non-restrictive conditions, with excellent yields and the ease of separating the catalyst from the reaction medium.
  • the demonstration of asymmetric induction by the use of an ionic compound according to the invention which carry a iral group is particularly important because of its generality and its ease of implementation.
  • Another subject of the present invention is therefore the use of the compounds of the invention as catalysts in the Friedel and Craft reactions, the Diels and Aider reactions, the aldolization reactions, the Michael additions, the allylation, pinacolic coupling reactions, glycosilation reactions, oxetane ring opening reactions, alkenes methathesis reactions, Ziegler-Natta type polymerizations, ring opening methathesis type polymerizations and polymerizations of the methathesis type of acyclic dienes.
  • the ionic compounds of the invention preferred for use as a catalyst for the above reactions are those in which the cation is chosen from lithium, magnesium, copper, zinc, tin, trivalent metals, including rare earths, platinoids, and their organometallic couples, in particular metallocenes.
  • the compounds of the invention can also be used as solvent for carrying out chemical, photochemical, electrochemical, photoelectrochemical reactions.
  • ionic compounds are preferred in which the cation is an imidazolium, a triazolium, a pyridinium or a 4-dimethylamino-pyridinium, said cation optionally carrying a substituent on the carbon atoms of the ring.
  • the compounds being used in their liquid form very particularly preferred are those which have a melting point of less than 150 ° C., more particularly less than 100 ° C.
  • the inventors have also found that the anionic charge carried by the group R F -SO x -N ⁇ Z exerted a stabilizing effect on electronic conductors of the conjugated polymer type, and that the use of a compound in which the substituent Z included a long alkyl chain made it possible to make these polymers soluble in the usual organic solvents even in the doped state.
  • the grafting of these charges onto the polymer itself gives polymers whose overall charge is cationic, soluble in organic solvents and having, in addition to their stability, anticorrosion properties with respect to metals, aluminum and ferrous metals.
  • the present invention also relates to electronically conductive materials comprising an ionic compound of the present invention in which the cationic part is a polycation constituted by a conjugated polymer doped "p".
  • the preferred ionic compounds for this application are those in which the substituent Z contains at least one alkyl chain having from 6 to 20 carbon atoms.
  • Z is R D Y-, R D being an alkyl radical.
  • R F is R A CF 2 -, R A CF 2 CF 2 -, R A CF 2 CF (CF 3 ) - or CF3C (R A ) F- in which R A - represents a alkyl radical.
  • Cationic type dyes are used more and more frequently as sensitizers for photographic films, for the optical storage of information (optical disks accessible for writing), for lasers.
  • cyanines are used more and more frequently as sensitizers for photographic films, for the optical storage of information (optical disks accessible for writing), for lasers.
  • the tendency of these conjugated molecules to pile up when they are in solid phases limits their use, due to variations in optical properties compared to the isolated molecule.
  • the use of ionic compounds of the invention for the manufacture of cationic dyes whose counter ions, possibly attached to this same molecule, correspond to the functionalities of the invention makes it possible to reduce the phenomena of aggregation, including in matrices solid polymers and stabilize these dyes.
  • Another subject of the present invention is a cationic dye composition, characterized in that it contains an ionic compound according to the invention.
  • the ionic compounds which are particularly preferred for this application are those in which the negative charge or charges of the anionic group R F -SO x -N ⁇ -Z are either fixed to the dye molecule, or they constitute the counterion of the positive charges of the dye. Examples of such compounds that may be mentioned include the following compounds:
  • Examples 1 to 7 describe the preparation of a few compounds used as reagents for the synthesis of the ionic compounds of the present invention.
  • Examples 8 to 78 illustrate the preparation of compounds according to the invention and their uses.
  • the corresponding sodium salt was prepared by reacting the trifluoromethanesulfonamide with the sodium carbonate Na 2 C03 in water (20% in excess). After evaporation of the water and drying, the product obtained was taken up in acetonitrile and then the excess carbonate was removed by filtration. After evaporation of the acetonitrile and drying, the sodium salt of trifluoromethanesulfonamide CF 3 S0 2 NHNa was obtained quantitatively.
  • the lithium CF 3 SO 2 NHLi and potassium CF 3 SO 2 NHK salts were obtained by a similar process, replacing the sodium carbonate with lithium carbonate and potassium carbonate respectively.
  • the lithium S0 2 NHLi and potassium FS0 2 NHK salts were obtained by a similar process, replacing the sodium hydroxide with lithium hydroxide and potassium hydroxide respectively.
  • a stream of chlorine CI 2 was then passed into 200 ml of water containing 28.5 g (150 mmol) of lithium pentafluoroethanesulfinate C 2 FsS ⁇ 2 Li.
  • a second phase appeared more rapidly dense than the water which was extracted with two 25 ml fractions of anhydrous dichloromethane.
  • Example 4 Perfluorobutanesulfonamide A 30.21 g (100 mmol) of perfluoro-1-butanesulfonyl fluoride C 4 F 9 SO 2 F (marketed by Aldrich) and 8.91 g (100 mmol) of ethyl carbamate C 2 H 5 O 2 CNH 2 in 100 ml of anhydrous tetrahydrofuran at 0 ° C., 1.75 g (220 mmol) of lithium hydride LiH 95% (sold by Aldrich) were added in portions. After stirring for 72 hours under argon, the reaction medium was centrifuged and filtered to remove the precipitate of lithium fluoride LiF and the excess of lithium hydride.
  • the corresponding sodium salt was prepared by reacting perfluoro-1-butanesulfonamide with sodium carbonate Na 2 C ⁇ 3 in water (20% in excess). After evaporation of the water and drying, the product obtained was taken up in tetrahydrofuran and then the excess carbonate eliminated by filtration. After evaporation of the tetrahydrofuran and drying, the sodium salt of perfluoro-1-butanesulfonamide C 4 FgS0 2 NHNa was obtained quantitatively.
  • the lithium and potassium salts were obtained by a similar process, replacing the lithium carbonate with sodium carbonate and potassium carbonate respectively.
  • the corresponding sodium salt was prepared by reacting perfluoroethanesulfonamide with sodium carbonate Na 2 C ⁇ 3 in water (20% in excess). After evaporation of the water and drying, the product obtained was taken up in tetrahydrofuran and then the excess carbonate was removed by filtration. After evaporation of the tetrahydrofuran and drying, the sodium salt of perfluoroethanesulfonamide C 2 FsS ⁇ 2 NHNa was obtained quantitatively. Microanalysis gave: H 0.42 (0.46); C 10.35 (10.87); N 6.73 (6.34); F 42.01 (42.97); Na 10.89 (10.4); S 14.25 (14.5).
  • the lithium and potassium salts were obtained by a similar process, replacing the sodium carbonate respectively with lithium and potassium carbonate.
  • the diazonium previously prepared was added over a period of 30 min. A little ether was added to decrease the amount of foam that forms after each addition.
  • the reaction medium was poured into 1 liter of a water-ice mixture (1: 1). After merger ice, a yellow oil was separated in a separatory funnel, then the aqueous phase was extracted with two fractions of 100 ml of ether. After addition of the ethereal phase to the collected oil, the solution was washed with a concentrated solution of sodium bicarbonate until neutral, then with water, and finally dried with magnesium sulfate.
  • Example 8 3-chloropropanesulfonyl (trifluoromethanesulfonyl) - imide Reacted in 50 ml of anhydrous tetrahydrofuran at 0 ° C, 17.7 g (100 mmol) of 3-chloropropanesulfonyl chloride Cl (CH 2 ) 3 SO 2 CI and 37.44 g (200 mmol) of the potassium salt of trifluoromethanesulfonamide CF 3 SO 2 NHK. After 3 hours at 0 ° C., then 24 hours at room temperature, the tetrahydrofuran was evaporated and the product was recrystallized from 40 ml of water, collected by filtration and dried.
  • the lithium salts were obtained quantitatively by treatment of the potassium salts in anhydrous tetrahydrofuran with the stoichiometric amount of anhydrous lithium chloride, filtration of the reaction medium, evaporation of the solvent and drying under vacuum.
  • These three salts are soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide). In the latter solvent at an O / K concentration of 14/1, they have an ionic conductivity greater than 10 ⁇ 3 S. cm -1 at a temperature of 100 ° C.
  • This salt has a conductivity of 2.3 ⁇ 10 ⁇ 4 " S. cm “ 1 at 60 ° C. in poly (ethylene oxide) at an O / Li concentration of 12/1.
  • the potassium salt of trifluoromethanesulfonyl (N-ethylsulfonyl) imide was obtained from ethylamine by a similar process and the salt of trifluoromethanesulfonyl potassium (N-propylsulfonyl) imide from propylamine.
  • the lithium salts were prepared quantitatively by ion exchange between the potassium salts and the lithium chloride in anhydrous tetrahydrofuran.
  • These compounds have a labile proton enabling nucleophilic substitution reactions to be carried out in the presence of a base with halides of alkyls or acids, for example.
  • the potassium salt of the fluorosulfonyl (5-formyl-2-furansulfonyl) imide was obtained by the same process.
  • the aldehyde function makes it possible to graft this salt on the substrates containing a group capable of reacting with this function, for example an amino group or a double bond.
  • the potassium salt of pentafluoroethanesulfonyl (2-propene-sulfonyl) imide (69% yield) was obtained according to the same process from the potassium salt of pentafluoroethanesulfonamide obtained in Example 5.
  • salts have the particularity of being able to be homo- or copolymerized by a polymerization initiated by the radical route or by a catalyst for the polymerization of olefins of the Ziegler-Natta type, such as a zircanocene, and more generally of being able to undergo the chemical reactions specific to the ethylene bonds .
  • the potassium salt of the 2,3-epoxypropane-1-sulfonyl (pentafluoroethanesulfonyl) imide was obtained according to the same procedure from the potassium salt of the pentafluoroethanesulfonyl (2-propenesulfonyl) imide obtained in the example. 12.
  • the lithium salts were obtained by treatment of the potassium salts in anhydrous tetrahydrofuran with the stoichiometric amount of anhydrous lithium chloride, filtration of the reaction medium, evaporation of the solvent and drying under vacuum.
  • These salts can be homo- or copolymerized by a polymerization initiated anionically or cationically. More generally, they can undergo the chemical reactions specific to oxetanes.
  • the homopolymer of the potassium salt of 2,3-epoxypropane-1-sulfonyl (trifluoromethanesulfonyl) imide was prepared by a polymerization in tetrahydrofuran initiated anionically by potassium tert-butoxide, then the lithium polysel by exchange. ionic with anhydrous lithium chloride.
  • the latter has a conductivity in a gelled medium (21% by weight of polyacrylonitrile, 38% of ethylene carbonate, 33% propylene carbonate, 8% of the homopolymer) of 1.1.10 ⁇ 3 S. cm -1 at 30 ° C.
  • the number of cationic transport in this electrolyte is 0.82.
  • this homopolymer is soluble in most usual organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers.
  • Example 14 Vinylsulfonyl (trifluoromethanesulfonyl) imide To a solution at 0 ° C. and under argon of 8.15 g (50 mmol) of 2-chloro-1-ethane-sulfonyl chloride CICH 2 CH 2 SO 2 CI (marketed by Aldrich ) and 7.45 g (50 mmol) of trifluoromethanesulfonamide CF 3 SO 2 NH 2 in 25 ml of anhydrous tetrahydrofuran, a solution of 16.83 g (150 mmol) of DABCO diluted in 30 ml was added dropwise over 30 min. 25 ml anhydrous tetrahydrofuran.
  • CICH 2 CH 2 SO 2 CI marketed by Aldrich
  • the lithium salt of the perfluorobutanesulfonyl (vinylsulfonyl) imide (99% yield) was obtained according to the same process from the perfluorobutanesulfonamide obtained in Example 4.
  • These salts can be homo- or copolymerized by a polymerization initiated by the radical route. More generally, they can undergo the chemical reactions specific to activated vinyl bonds, in particular Michael additions, with an alcoholate for example.
  • the lithium salt was obtained quantitatively by treatment of the potassium salt in anhydrous tetrahydrofuran with the stoichiometric amount of anhydrous lithium chloride, filtration of the reaction medium, evaporation of the solvent and drying under vacuum.
  • This salt can be homopolymerized cationically. It can also be copolymerized cationically, optionally, by an alternating polymerization with an unsaturated monomer. More generally, it can undergo the chemical reactions specific to alkyl vinyl ethers.
  • the homopolymer prepared by a polymerization in anhydrous acetonitrile initiated cationically by bis (trifluoromethanesulfonyl) imide has a conductivity at a concentration of 0.8 M in a mixture of dimethylcarbonate and ethylene carbonate (2: 1) from 6.10 "3 S. cm " 1 to 30 ° C.
  • this homopolymer is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • organic solvents tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • aprotic solvating polymers such as poly (ethylene oxide).
  • Example 16 4-styrenesulfonyl (trifluoromethanesulfonyl) imide
  • the lithium salts of the fluorosulfonyl (4-styrenesulfonyl) imide were prepared according to the same process from the fluorosulfonamide obtained in Example 2, from the pentafluoroethanesulfonyl (4-styrenesulfonyl) imide. (97% yield) from pentafluoroethanesulfonamide obtained in Example 5 and perfluorobutanesulfonyl (4-styrenesulfonyl) imide (99% of yield) from perfluorobutanesulfonamide obtained in Example 4.
  • salts can be homo- or copolymerized by an anionic, cationic and more particularly radical-initiated polymerization. They can also be grafted onto a polymer matrix such as polyvinylidene fluoride by irradiation.
  • these salts In poly (ethylene oxide) at an O / Li concentration of 16/1, these salts have a conductivity ⁇ 6.10 "4 S.cm -1 at 100 ° C.
  • these homopolymers can be used as catalysts for Diels-Alder reactions, in this sense they behave like chemical micro-reactors.
  • Example 17 5- (4-methylene-1,3-dioxolane) - 2-furanesulfonyI (trifluoromethanesulfonyl) imide
  • the lithium salt was obtained quantitatively by treatment of the potassium salt in anhydrous tetrahydrofuran with the stoichiometric amount of anhydrous lithium chloride, filtration of the reaction medium, evaporation of the solvent and drying under vacuum.
  • This salt can be homo- or copolymerized by a polymerization initiated by the cationic or radical route.
  • the homopolymer of this salt was obtained by photopolymerization, initiated cationically by the irradiation of tris (4-methylphenyl) sulfonium hexafluoro- antimonate with a UV lamp for 10 min at 36 ° C. It has a conductivity at a concentration of 0.5 M in tetraethylsulfamide (C 2 H 5 ) 2 NS0 2 N (C 2 H 5 ) of 4.10 "3 S. cm" 1 at 20 ° C.
  • Example 18 1-acryloyl-2,2,2-trifluoroethanesulfonyl- (trifluoromethanesulfonyl) imide
  • This salt can be homo- or copolymerized by photopolymerization in the presence of a photosensitizer.
  • a mixture containing this salt (16% by weight), poly (ethylene glycol) dimethacrylate having a molar mass of 600 g / mol (81% by weight, marketed by Aldrich), silica particles having a specific surface was produced. 300 m 2 / g (3% by weight, Aerosil, marketed by Degussa AG) and xanthone.
  • This solution was deposited with a spinner on a glass plate covered with a layer of tungsten trioxide W0 3 and a conductive underlay of tin oxide.
  • An optically transparent, visible membrane was obtained which adhered to the support by photopolymerization triggered by irradiation using a UV lamp for 10 min at 32 ° C.
  • An electrochromic system was then produced by assembling in a glove box a counter electrode constituted by the deposition on a glass plate of a layer of hydrogenated iridium oxide H x lr0 2 and of a sublayer of oxide d 'tin. This electrochromic gave a variation of the optical absorption of 80%
  • the lithium salt of pentafluoroethanesulfonyl (3-maleimido-propanesulfonyl) imide (98% yield) was obtained according to the same process from the potassium salt of pentafluoroethanesulfonyl (3-chloropropanesulfonyl) imide obtained in Example 8.
  • salts can be homopolymerized by the radical route or by the anionic route or copolymerized by the anionic route or by the radical route optionally by alternating polymerization with an electron donor monomer (N-vinyl-2-pyrrolidone, N-vinyl formamide, vinyl ether, ).
  • an electron donor monomer N-vinyl-2-pyrrolidone, N-vinyl formamide, vinyl ether, .
  • Example 20 2- (triethoxysilyl) ethanesulfonyl (trifluoromethane-sulfonyl) imide
  • homopolymers or copolymers with various alkoxysilanes can be obtained in a protic medium, optionally in the presence of a catalyst (acid, base, fluoride, etc.).
  • a catalyst acid, base, fluoride, etc.
  • a copolymer was prepared by polycondensing the potassium salt of trifluoromethanesulfonyl- (2- (triethoxysilyl) ethanesulfonyl) imide with O- [2- (trimethoxysilyl) ethyl] -O '-methylpolyethylene glycol of mass 5000 (marketed by Shearwaters Polymers ) (5: 1 molar) in a water / methanol mixture, using as trifluoromethanesulfonyl (2- (triethoxysilyl) ethane-sulfonyl) imide catalyst. After a few hours the solution was concentrated.
  • An activated carbon felt previously degassed, having a specific surface of 1500 m / g (sold by the company Actitex) was then impregnated with the viscous liquid obtained. After drying, this operation was repeated to perfect the impregnation. After maintaining the felt impregnated for one week in an oven at 50 ° C, two pellets with a diameter of 2 cm were cut with a cookie cutter. A sheet of cigarette paper (sold by Bolloré Technologies) was then impregnated with a viscous liquid identical to that used to impregnate the carbon felt. This sheet was deposited between the two pads of impregnated felt which serve as carbon electrodes.
  • a potassium salt solution of trifluoromethanesulfonyl- (2- (triethoxysilyl) ethanesulfonyl) imide was also prepared with O- [2- (trimethoxysilyl) ethyl] -O '-methylpolyethylene glycol of mass 5000 (sold by Shearwaters Polymers) (3: 1 molar) in a water / methanol mixture.
  • Example 21 bis [3- (trimethoxysilyl) propyl] aminosulfonyl (trifluoromethanesulfonyl) imide
  • This compound has properties similar to those of the compound of Example 20 and can be used for the same applications.
  • This electrolyte has an ionic conductivity greater than 10 "5 S 1. Cm -1 at 60 ° C. The number of cationic transport is 0.92.
  • the lithium salt was obtained quantitatively by treatment of the potassium salt in anhydrous tetrahydrofuran with the stoichiometric amount of anhydrous lithium chloride, filtration of the reaction medium, evaporation of the solvent and drying under vacuum.
  • This salt can be homo- or copolymerized by a polymerization initiated by the radical route.
  • a film of polymer electrolyte, with a thickness of 30 ⁇ m, consisting of the lithium salt dissolved in a matrix of poly (ethylene oxide) having ethylenic unsaturations, at a concentration O / Li 26 was produced. / 1, and containing 1% by weight of cyanovaleric acid and 3% by weight of silica with a specific surface of 300 m 2 / g (Aerosil, marketed by Degussa AG).
  • This polymer was obtained by polycondensation of polyethylene glycol of mass 1000 with 3-chloro-2-chloromethyl-1-propene according to the procedure described by Alloin & al.
  • the corresponding acids were obtained by extraction with ether of acidified aqueous solutions of the various potassium salts.
  • the lithium salts were obtained by treatment of the various acids with lithium carbonate Li 2 C0 3 .
  • These salts can be homo- or copolymerized by a polymerization initiated by the radical route.
  • This membrane can also be used for the heterogeneous Friedel-Crafts catalysis of the acylation reaction of toluene with benzoyl chloride.
  • Example 24 2,2-fluorovinylsulfonyl (trifluoromethane-sulfonyl) imide Under argon, at 6.02 g (20 mmol) of the lithium salt of trifluoromethane-sulfonyl (2, 2, 2-trifluoroethanesulfonyl) imide), obtained at 1 Example 9, in solution in 40 ml of anhydrous tetrahydrofuran at -20 ° C, 10 ml of a 2 M solution of butyllithium in cyclohexane C 4 HgLi (20 mmol, sold by Aldrich) was added slowly.
  • This salt can be homo- or copolymerized by a polymerization initiated by the radical route.
  • the precipitate of DABCO hydrochloride was removed by filtration on a sintered glass of porosity No. 4. 4.24 g (100 mmol) of anhydrous lithium chloride were then added, the reaction medium was stirred for 24 hours, then it was again filtered to remove the DABCO hydrochloride formed. After evaporation of the tetrahydrofuran and drying, 25.17 g (96% yield) of the lithium salt of trifluoromethanesulfonyl- were recovered.
  • the lithium salt of pentafluoroethanesulfonyl (dimethylaminosulfonyl) imide (98% yield) was prepared according to the same process from the pentafluoroethanesulfonamide obtained in Example 5.
  • the precipitate of DABCO hydrochloride was removed by filtration on a sintered glass of porosity No. 4. After evaporation of the tetrahydrofuran and drying, the product was dissolved in 25 ml of ethanol. Then added 9.81 g (100 mmol) of potassium acetate CH 3 COOK, then the precipitate obtained was recrystallized under reflux of ethanol. After cooling, filtration and drying, 24.13 g (82% yield) of the potassium salt of the trifluoromethanesulfonyl- (dimethylaminosulfonyl) imide Me 2 NS ⁇ 2 NKS ⁇ 2 CF 3 having a purity characterized by NMR of fluorine and proton greater than 99%.
  • the potassium salt of the perfluorobutanesulfonyl (dimethylaminosulfonyl) imide (85% yield) was obtained by the same process from the perfluorobutanesulfonamide obtained in Example 4.
  • This conductivity is identical to that determined for the potassium salt alone, which indicates a vehicle transport mechanism for lithium in the electrolyte complexed by the anions and thus moving in the form of an anionic complex interacting little with the basic solvent. .
  • This type of conductivity is very favorable for the operation of lithium generators and more particularly those with polymer electrolytes, the performances during power calls being improved.
  • This salt is an initiator of radical polymerization soluble in most of the usual organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers, unlike the hydrochloride of 2, 2 '-azobis (2-methylpropionamidine).
  • a solution in acetonitrile of 1 part of this initiator and 100 parts of a polymer containing ethylenic unsaturations was prepared.
  • This polymer was obtained by polycondensation of polyethylene glycol of mass 1000 with 3-chloro-2-chloromethyl-1-propene according to the procedure described by Alloin & al. (Solid States Ionics, (1993), 60, 3).
  • the viscous solution obtained was poured onto a polypropylene (PP) film. After evaporation of the solvent, the polymer film with a thickness of 110 ⁇ m on PP was stored for one week in a glove box under argon to dry it. Crosslinking was then initiated by bringing the temperature of the film to 60 ° C.
  • the solubility of the initiator used in the polymer matrix therefore makes it possible to obtain efficient and homogeneous crosslinking.
  • this initiator is not volatile, unlike for example the 2,2'- azobisisobutyronitrile, and the amount added can best be optimized for each type of polymerization.
  • Example 28 Dialkylaminosulfonyl (trifluoromethanesulfonyl) imide 25.85 g (200 mmol) of dibutylamine (C 4 H 9 ) 2 NH in solution in 50 ml of anhydrous tetrahydrofuran were treated with 27.83 g (200 mmol) of sulfur trioxide complexed with trimethylamine (CH 3 ) 3 N "S ⁇ 3 . After stirring for 24 hours at room temperature, the solvent was evaporated and the product taken up in 40 ml of methanol.
  • the potassium salts of the amides carrying diethyl substituents (C 2 H 5 ) 2 NS0 2 NKS0 2 CF 3 (66% yield) were prepared using diethylamine, and di-2-ethylhexyl [2], according to a similar process.
  • the various potassium salts of the fluorosulfonyl- (dialkylaminosulfonyl) imides were prepared by a similar process, from the fluorosulfonamide obtained in Example 2, the potassium salts of the pentafluoroethanesulfonyl (dialkylaminosulfonyl) imides from the pentafluoroethanesulfonamide obtained. in Example 5 and the potassium salts of the perfluorobutanesulfonyl (dialkylaminosulfonyl) imides (C 4 H 9 ) 2 NS0 2 NKS0 2 C 4 F 9 from the perfluorobutanesulfonamide obtained in Example 4.
  • This salt is very soluble in sparingly polar solvents such as dichloromethane or methylene chloride as well as in sparingly polar polymer matrices such as polymethyl methacrylate.
  • sparingly polar solvents such as dichloromethane or methylene chloride
  • sparingly polar polymer matrices such as polymethyl methacrylate.
  • An electrochromic system was then produced by glove box using this electrolyte enclosed between a first electrode constituted by the deposition on a glass plate of a layer of hydrogenated iridium oxide H x lr0 2 and of a conductive underlay of tin oxide and a second electrode consisting of a layer of tungsten trioxide 0 3 and a conductive underlay of tin oxide.
  • This electrochromic allowed a variation of the optical absorption from 80% (discolored state) to 30% (colored state) and good cycling performance (more than 20,000 coloring / discoloration cycles)
  • An electrochromic was also produced by dissolving two complementary dyes in such a molten salt: in a glove box, 1.62 g (5 mmol) of the imidazolium salt of trifluoromethanesulfonyl (dimethylaminosulfonyl) imide was co-ground with 1, 02 g of imidazole (15 mmol).
  • Such an electrochromic system is easy to implement, even for large systems (greater than 1 m) which use both glass and a polymer suitably treated as a transparent conductive electrode.
  • the energy required to maintain the coloring is relatively low, less than 1 / m 2 .
  • This salt is very soluble in the usual organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, gly es, ). It has an interaction with weakly polar solvents such as dichloromethane better than that of the lanthanum salt of the bis (trifluoromethanesulfonyl) imide. It can be used as a catalyst in Diels-Alder reactions.
  • Example 31 Dialkylaminosulfonyl (trifluoromethanesulfonyl) imide
  • reaction medium was filtered to remove the insoluble potassium tetrafluoroborate, and a 1 M solution of trifluoromethanesulfonyl- was thus obtained.
  • These salts are particularly advantageous for doping conjugated polymers (polythiophene, polypyrrole, etc.) to which they confer appreciable electronic conductivity.
  • Example 32 Dialkylaminosulfonyl (trifluoromethanesulfonyl) imide 5.96 g (40 mmol) of trifluoromethanesulfonamide CF3SO 2 NH 2 and 9.9 ml of pyridine in 60 ml of anhydrous dichloromethane were cooled to -20 ° C. 5.4 g (40 mmol) of sulfuryl chloride SO 2 CI 2 diluted in 10 ml of anhydrous dichloromethane were then added dropwise, followed by 8.1 g (80 mmol) of dipropylamine (C 3 H 7 ) 2 NH . The mixture was stirred for 1 hour at -20 ° C and then for 24 hours at room temperature.
  • the reaction medium was then filtered, then the solvent evaporated.
  • the recovered product was taken up in 50 ml of water, acidified to a pH ⁇ 2 with a 4 M hydrochloric acid solution, the aqueous phase extracted twice with 20 ml of ether, the organic phase dried with sulfate. magnesium, then evaporated ether. After sublimation of the compound obtained under secondary vacuum at 40 ° C., 11 g of trifluoromethanesulfonyl (dipropylaminosulfonyl) imide were recovered (88% yield) having a purity characterized by fluorine and proton NMR greater than 98%.
  • the lithium salt was prepared by assaying the pH in metric acid in solution in water with a titrated solution of lithium hydroxide. After evaporation of the water and drying under vacuum at 60 ° C for 24 hours, the lithium salt of trifluoromethanesulfonyl (dipropylaminosulfonyl) - imide (C 3 H 7 ) 2 NS0 2 was quantitatively recovered in the form of a white powder. NLiS0 2 CF 3 .
  • the lithium salt of trifluoromethanesulfonyl (N-methyl-N-ethylaminosulfonyl) imide CH 3 (C 2 H 5 ) NS ⁇ 2 NLiS ⁇ 2 CF 3 having a purity determined by proton NMR and higher fluorine was prepared according to the same process. 99% with a yield of 76%.
  • salts are soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • the lithium salt trifluoromethanesulfonyl- (dipropylaminosulfonyl) imide has a conductivity of
  • the lithium salt was prepared by treating the acid obtained with lithium phosphate Li 3 P0 for 48 hours in acetonitrile. After filtration of the reaction medium, evaporation of the solvent and drying under vacuum at 60 ° C for 24 hours, the lithium salt of trifluoromethanesulfonyl (3- (trifluoromethyl) phenyl) amide m-CF 3 C 6 H was obtained quantitatively. 4 NLiS0 2 CF 3 .
  • the sodium and potassium salts were obtained by a similar process, replacing the lithium phosphate with sodium and potassium phosphate respectively.
  • trifluoromethanesulfonyl (3-5-bis (trifluoromethyl) - phenyl) amide (I) was also prepared from 3-5-bis (trifluoromethyl) aniline, trifluoromethanesulfonyl (4-tri-fluoromethoxy) phenyl) amide (II) from trifluoromethanesulfonyl (4-trifluoromethoxy) aniline, trifluoromethanesulfonyl (4-aminopyridine) amide (III) from 4-aminopyridine and trifluoromethanesulfonyl (2, 2, 2-trifluoroethyl) amide ( IV) from 2, 2, 2-trifluoroethylamine as well as the corresponding lithium, sodium and potassium salts.
  • the tin (II) salts can be used for the catalysis of aldolic condensations.
  • Example 34 Trifluoro-methane-sulfonyl (2-trifluoromethyl-1,3,4-thiadiazole-5-amino) amide.
  • the lithium salt was obtained by treating the acid with lithium carbonate Li 2 C0 3 in water.
  • This salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • This salt has an oxidation potential in a mixture of ethylene carbonate and dimethylcarbonate (2: 1), at a concentration of 1 M, greater than 4 V with respect to a lithium anode.
  • Example 35 Trifluoro-methane-sulfonyl (2-trifluoromethyl-thiadiazole-5-aminosulfonyl) imide.
  • 5-trifluoromethyl-1,3,4-thiadiazole-2-sulfonyl chloride was prepared from 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (marketed by Aldrich ), following the procedure described in Example 7.
  • This salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • This salt has an oxidation potential, at a concentration of 0.5 M in acetonitrile, greater than 4.5 V with respect to a lithium anode. It can be used for Li-Ion batteries with liquid electrolytes or gels.
  • a battery was assembled using an anode constituted by carbon coke (80% by volume) mixed with polyvinylidene fluoride (PVDF, sold by the company Montedison) as binder (20% by volume), a compound electrolyte of a mixture of ethylene carbonate and dimethylcarbonate (2: 1), gelled with PVDF, containing this salt at a concentration of 1 M and a composite cathode constituted by carbon black (6% by volume), Li 2 Mn0 4 (75% by volume) and PVDF as binder (20% by volume).
  • PVDF polyvinylidene fluoride
  • Example 36 Trifluoro-methane-sulfonyl (2-trifluoromethyl-thiadiazole-5-aminosulfonyl) amide.
  • the lithium trisel was obtained by ion exchange with litihum chloride LiCl in tetrahydrofuran.
  • the lithium salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • organic solvents tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide).
  • O / Li 12/1
  • the number of cationic transport is from 0.52 to 60 ° C.
  • the tetrabutylammonium tri-salt was obtained by treatment of the lithium tri-salt with tetrabutylammonium chloride (5% excess) in water.
  • the precipitate obtained was then recovered by extraction with dichloromethane, the dichloromethane solution was washed with water, then evaporated.
  • the tri-tetrabutylammonium tri-salt was recovered quantitatively from the tris- [1, 3, 5-trifluoromethanesulfonamide] -2, 4, 6-triazine.
  • the addition of 3.5% by weight of this compound to a poly (acrylonitrile-co-butadiene) copolymer containing ⁇ 20% by weight of acrylonitrile gives the copolymer antistatic properties.
  • Example 37 Trifluoromethanesulfonyl (1,1,1,3,3,3-hexafluoro- 2-propanoxysulfonyl) imide 5.96 g (40 mmol) of trifluoromethanesulfonamide CF 3 SO 2 NH 2 and 9.9 ml of pyridine in 60 ml anhydrous dichloromethane, were cooled to -15 ° C. 5.4 g (40 mmol) of sulfuryl chloride S0 2 C1 2 diluted in 10 ml of anhydrous dichloromethane were then added dropwise, then 6.72 g (40 mmol) of 1, 1, 1, 3, 3 , 3-hexafluoro-2-propanol (CF 3 ) 2 CHOH.
  • aqueous solution of the lithium salt was obtained by treating the acid with lithium carbonate Li 2 C0 3 in water. Then, by addition of 1-ethyl-3-methyl-1H-imidazolium chloride (10% excess, marketed by Aldrich), a liquid phase more dense than water was obtained. This phase was recovered by extraction with dichloromethane. After evaporation of the dichloromethane and drying under vacuum at 40 ° C. of the liquid obtained, the molten salt of l-ethyl-3-methyl-1H-imidazolium of trifluoromethanesulfonyl (1,1,1,3,3, 3-hexafluoro) was recovered - 2-propanoxysuifonyl) imide (91% yield).
  • CCee sseell ffoonndduu has a conductivity of
  • An electrochemical photovoltaic cell was produced by assembling a system composed of two electrodes separated by an empty space with a thickness of 30 ⁇ m.
  • the first electrode was coated with a nanoparticulate layer of titanium dioxide Ti0 2 0.25 ⁇ m thick on which the 1,3-phenylsulfonamide-N, N'-trifluoromethanesulfonyl rhodamine B obtained was adsorbed.
  • Example 55 as a sensitizer.
  • the space between the electrodes was filled with an electrolyte composed of salt melt in which 10% by weight of methylhexyl imidazolium iodide and 10 mmol of iodine had been dissolved.
  • the short-circuit current of this cell is 103 ⁇ A.c ⁇ f and its open circuit voltage of 552 mV.
  • the potassium salts of cyano (fluorosulfonyl) imide (I) were prepared from fluorosulfonyl chloride C1S0 2 F, of cyano (trifluoromethanesulfonyl) imide (II) from trifluoromethanesulfonyl chloride CF 3 S0 2 C1 and cyano (pentafluoroethanesulfonyl) imide (III) from pentafluoroethanesulfonyl chloride C 2 F 5 S0 2 C1.
  • Electrochemical supercapacity was achieved using a 1 M solution of each of the above potassium salts in acetonitrile as electrolytes and carbon / aluminum composites as electrodes.
  • the electrodes with a thickness of 150 ⁇ m were placed on either side of a microporous polyethylene with a thickness of 40 ⁇ m impregnated with and the complete system sealed in a glove box in a battery case button.
  • Good performances have been obtained with these supercapacitors (more than 100,000 charge / discharge cycles between 0 and 2.5 V for an energy density greater than 25 h / 1 and a delivered power greater than 1500 W / l).
  • Example 39 Alkylsulfonyl (trifluoromethanesulfonyl) imide
  • trifluoromethanesulfonyl (octylsulfonyl) imide (I) and trifluoromethanesulfonyl (dodecylsulfonyl) imide (II) were obtained under identical conditions from octylsulfonyl chloride and dodecylsulfonyl chloride respectively.
  • the lithium salts of these three derivatives were prepared quantitatively by ion exchange between the potassium salt and the lithium chloride in anhydrous tetrahydrofuran.
  • the lanthanum salt of fluorosulfonyl (butane-sulfonyl) imide C 8 H 17 SO 2 NKSO 2 F can be used as catalyst for Diels-Alder reactions, in particular in dichloromethane.
  • the lithium salt was prepared by ion exchange (metathesis) between the potassium salt and the lithium chloride in anhydrous tetrahydrofuran.
  • Example 42 1-dodecyl-1,1,1,3,3,3-hexafluoro-2-propanoxysulfonyl (trifluoromethanesulfonyl) imide
  • the lithium salt was obtained quantitatively by treatment of the potassium salt in anhydrous tetrahydrofuran with the stoichiometric amount of anhydrous lithium chloride, filtration of the reaction medium, evaporation of the solvent and drying under vacuum.
  • salts can be used as additives for the rolling of lithium and for the extrusion of polymers, in particular the extrusion of poly (ethylene oxide). They have plasticizing properties.
  • Example 43 Igepal® CA-520-propylsulfonyl (trifluoromethanesulfonyl) imide.
  • Igepal® CA-520 10 mmol, sold by Aldrich
  • 3.28 g (10 mmol) of trifluoromethanesulfonyl (3-chloropropanesulfonyl) - imide obtained in the example 8 in the presence of 4.24 g of potassium phosphate K 3 P0 4 (20 mmol).
  • the reaction medium was filtered in order to remove the potassium phosphate and the potassium chloride formed during the reaction. 7.18 g of the potassium salt of Igepal® CA-520-propylsulfonyl- were recovered after evaporation of the solvent and drying.
  • This salt is an excellent additive for the extrusion of poly (ethylene oxide). It also makes it possible to plasticize a large number of polymers containing polar units (ether, amide, nitrile, ester, etc.), while giving them a high ionic conductivity.
  • Example 45 0.0 '- [propylsulfonyl- (trifluoromethanesulfonyl) imide] polyethylene glycol.
  • a sulfonated poly (ethylene oxide) oligomer was prepared in the following manner: 12 g of poly (ethylene glycol) of mass 600 ( ⁇ 40 mmol of hydroxyl functions) were dried by azeotropic distillation with benzene and by lyophilization . After adding 50 ml of anhydrous tetrahydrofuran, the terminal hydroxyl groups were metallized with potassium-naphthalene. The stoichiometry was determined by colorimetry, the end of the reaction being indicated by the persistence of the intense green color of the anion radical of naphthalene. Then added 4.89 g of 1,3-propane sultone
  • This salt is soluble in most polar organic solvents (acetonitrile, tetrahydrofuran,
  • the potassium salt of trifluoromethanesulfonyl- (S (+) -1-phenyl-2,2,2,2-trifluoroethanoxysulfonyl) imide (66% yield) was obtained from R (-) -l- phenyl-2, 2, 2-trifluoroethanol.
  • the lithium salts were obtained by ion exchange (metathesis) in tetrahydrofuran with lithium chloride.
  • the lanthanum salts were obtained by treating the potassium salts with a stoichiometric amount of lanthanum perchlorate La (C10 4 ) 3 , 6H 2 0 in a mixture of acetonitrile and isopropyl orthoformate intended to remove the water lanthanum salt crystallization. After filtration to remove the precipitate of potassium perchlorate KC10 4 and evaporation of the solvent, the lanthanum salts of the two enantiomers of trifluoromethanesulfonyl- (1-phenyl-2,2,2,2-trifluoroethanoxysulfonyl) imide were recovered quantitatively.
  • Example 47 Trifluoromethanesulfonyl (N-methoxybutyl-N-2-butyl-3-methyl) aminosulfonyl) imide
  • the two enantiomers of the potassium salt of trifluoromethanesulfonyl (N-methoxybutyl-N-2-butyl-3-methyl) aminosulfonyl) imide have been obtained by a / 01013
  • the lithium salts were obtained by ion exchange (metathesis) in tetrahydrofuran with lithium chloride.
  • the lanthanum salts of the two enantiomers of trifluoromethanesulfonyl- (N-methoxybutyl-N-2-butyl-3-methyl) aminosulfonyl) -imide and of the two enantiomers were obtained by a process similar to that described in Example 46. fluorosulfonyl- (N-methoxybutyl-N-2-butyl-3-methyl) aminosulfonyl) imide.
  • Example 48 Camphorsulfonyl (trifluoromethanesulfonyl) imide. According to a process similar to that described in Example 39, the potassium salt of (1R) - (-) -10-camphorsulfonyl (trifluoromethanesulfonyl) imide was obtained from the chloride of (1R) - (-) - 10-camphorsulfonyl (marketed by Aldrich), and the potassium salt of (IS) - (+) -10-camphor-sulfonyl (trifluoromethanesulfonyl) imide from 01013
  • the lithium salts were obtained by ion exchange (metathesis) in tetrahydrofuran with lithium chloride.
  • the scandium salt was obtained by treating the potassium salt with a stoichiometric amount of scandium tetrafluoroborate Sc (BF 4 ) 3 in acetonitrile. After filtration to remove the precipitate of potassium tetrafluoroborate KBF and evaporation of the solvent, the scandium salt of trifluoromethanesulfonyl (N- (IS) - (+) - ketopinic-acetyl-N-methylsulfonyl)) was quantitatively recovered, after drying. imide.
  • the trifluoromethanesulfonyl (N, N-di-2-ethylhexylaminosulfonyl) imide salt of diphenyliodonium was prepared by the same method with a yield of 98% and having a purity characterized by proton and fluorine NMR greater than 99%.
  • Example 51 (4-butoxybenzene) - [trifluoromethanesulphonyl- (4-phenylsulphonyl) imide)] - iodonium
  • (4-butoxybenzene) -_ [pentafluoroethanesulphonyl- (4-phenylsulphonyl) imide)] iodonium was obtained by a similar process from pentafluoroethanesulfonamide and (4-butoxybenzene) - [perfluorobutanesulphonyl- (4-phenyl- sulphonyl) imide)] iodonium from perfluorobutanesulfonamide.
  • Example 52 Tetrakis (acetonitrile) palladium (ll) trifluoromethane-sulfonyl (N, N-di-2-ethylhexylaminosulfonyl) imide
  • Trifluoromethanesulfonyl- (N, N-di-2-ethylhexylaminosulfonyl) imide of tetrakis- (acetonitrile) palladium (II) was obtained quantitatively.
  • This salt is useful as a catalyst for vinyl polymerization of norbornene.
  • norbornene in nitromethane was polymerized at room temperature in the presence of 300 ppm of this salt. After 2 hours, the reaction medium was reprecipitated in methanol. Polynorbornene with a number average mass of 420,000 was obtained with a yield of 82%.
  • This fluorescent salt is soluble in most polar organic solvents (acetonitrile, tetrahydrofuran, DMF, ).
  • the magnesium salt of N-trifluoromethanesulfonyl-2-aminoacridine was obtained by the action of trifluoromethanesulfonyl chloride on the magnesium of 2-aminoacridine in tetrahydrofuran. After evaporation of the solvents, the product was taken up in water and treated with tetraethylammonium bromide (10% excess) in water, a precipitate then appeared.
  • the tetraethylammonium salt of N-fluorosulfonyl-2-aminoacridine was similarly obtained from fluorosulfonamide.
  • This salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in aprotic solvating polymers such as poly (ethylene oxide), as well as in polymers not very polar like polymethyl methacrylate.
  • the potassium disel of 1,3-phenylsulfonamide-N, N '-fluorosulfonyl rhodamine B was obtained from the potassium salt of fluorosulfonamide, the potassium disel of 1,3-phenylsulfonamide- N, N '-trifluoromethanesulfonyl rhodamine B from the potassium salt of trifluoromethanesulfonamide and the potassium disel from 1,3-phenylsulfonamide-N, N' -pentafluoroethanesulfonyl rhodamine B from pentafluorosulfonamide.
  • the lithium salts were obtained by metathesis with lithium chloride in tetrahydrofuran. These zwitterions have intense coloring properties. They are soluble in polar polymers and allow the constitution of dye lasers. The sulfonimide groups also allow them to adsorb on oxides, in particular nanoparticulate titanium dioxide; they then play a role in raising awareness of visible radiation, in particular in applications to photovoltaic cells.
  • Example 56 trifluoromethanesulfonyl (anthracenyl-9-ethanesulfonyl) imide
  • This salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in polar polymers.
  • This salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in polar polymers to which they give an intense blue color and stable with respect to light.
  • This salt, as well as analogous nickel, iron or manganese salts are useful as catalysts for oxygen reduction
  • the potassium salt of trifluoromethane sulfonyl ((4,6-dinitro-2-trifluoromethyl) phenyl) amide was obtained from 10.82 g of 2-chloro-3,5-dinitrobenzo- trifluoride (40 mmol, marketed by Aldrich), having a purity determined by NMR of fluorine, proton and carbon greater than 99%.
  • the lithium salts were obtained by ion exchange with lithium chloride in THF.
  • the lithium salt was obtained by treating the acid with lithium carbonate Li 2 CO 3 in water.
  • Example 60 1.1 '- (propylsulfonamide-N-trifluoromethanesulfonyl) ferrocene
  • the dilithian of ferrocene complexed by tetramethylethylenediamine was prepared in the following manner: Operating in a glove box under argon, 37 ml of TMEDA (247 mmol) were placed freshly distilled and 40 ml of anhydrous hexane in a 1-liter flask. 154 ml of a 1.6 M solution of butyllithium in hexane (247 mmol, sold by Aldrich) were then added dropwise. After 10 min, 18.6 g of ferrocene (100 mmol) in solution in 500 ml of anhydrous hexane while maintaining strong stirring of the solution.
  • TMEDA tetramethylethylenediamine
  • the potassium di-salt of 1,1 '- (propylsulfonamide-N-fluorosulfonyl) ferrocene was obtained by a similar process.
  • the lithium salts were obtained by treating the acid with lithium carbonate Li 2 C0 3 in water.
  • the salts make it possible to carry out overload protection, thus playing a role of redox shuttle. They also make it possible to produce electrochromic dye systems.
  • Example 61 9-10- (propylsulfonamide-N-trifluoromethanesulfonyl) phenazine
  • This salt is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes, ...) and in polar polymers.
  • This salt has two reversible redox couples.
  • poly (ethylene oxide) we have highlighted, on a platinum electrode with a diameter of 125 ⁇ m, a first redox couple with a potential aside 3.2 V and a second redox couple with a potential ⁇ 3.8 V, these potentials being measured with respect to a lithium electrode.
  • this salt By dissolving in a liquid, gel or polymer electrolyte, this salt allows a overload protection thus playing a redox shuttle role.
  • This salt can also be used in electrochromic dye systems.
  • An electrochromic glazing was thus produced by depositing on a glass plate covered with a conductive layer of ITO (indium and tin oxide), a solution in acetone of this compound and of poly (benzodiimide-co -ethylene oxide) having a molar mass ⁇ 1100 g / mole. After evaporation of the solvent and drying, a second glass electrode covered with a conductive layer of ITO (indium tin oxide) was deposited on the copolymer layer in a glove box. After sealing the assembly to make it waterproof, a potential of 1250 mV was applied to the exterior using a potentiostat. The system then became colored in intense blue. By applying a potential of -500 mV, a relatively rapid discoloration of the system was observed (less than 60 s).
  • Such an electrochromic system is easy to implement, even for large systems (greater than 1 m) which use both glass and a polymer suitably treated as a transparent conductive electrode.
  • the energy required to maintain the coloring is relatively low, less than 1 / m.
  • Example 62 2,2'-Azinobis (3-ethylbenzothiazoline-6 (sulfonyl (trifiuorométhanesulfonyi) imide).
  • the sodium disel of the acid 2, 2 '-azinobis (3-ethylbenzo-) was prepared.
  • thiazoline-6-sulfonic) from its ammonium disel (sold by Aldrich), treating it with a titrated solution of sodium hydroxide. After evaporation and drying, it was recovered quantitatively the sodium disel.
  • the tetraethylammonium disel was prepared by treating this product with tetraethylammonium chloride in water. The tetraethylammonium di-salt was then recovered by extraction with dichloromethane.
  • This compound gives by oxidation a radical and a biradical which are stable zwitterions.
  • it is useful as an oxidation catalyst between an oxygenated aqueous phase and an immiscible organic phase containing the species to be oxidized.
  • This electronic conductive polymer has an electronic conductivity determined by the method of the four tips of 8.7 S. cm " This conductivity is stable even when the material is exposed to air.
  • Example 42 1-dodec ⁇ l-l, 1, 1, 3,3,3-hexafluoro- 2-propanoxysul onyl (trifluoromethanesulfonyl) imide
  • This polymer compound which comprises a doping anion very delocalized in its structure has properties of electronic conductor (PCE).
  • PCE electronic conductor
  • the low basicity of this anion improves the stability of the polymer, in particular in a humid environment.
  • the battery had the following constitution: a composite cathode constituted by 40% by volume of the polymer compound obtained in the present example and 60% by volume of poly (ethylene oxide) of mass 3.10; an electrolyte consisting of a poly (ethylene oxide) film of mass 5.10 containing the lithium salt of trifluoromethanesulfonyl-
  • the battery obtained was cycled at a temperature of 60 ° C between 3 V and 3.9 V. More than
  • the polymer compound of the present example is a good corrosion inhibitor of ferrous metals in an acid or chloride medium.
  • the treatment of the surfaces to be protected is carried out simply by depositing a solution of PCE in a mixture of water and dimethylformamide, in the form of a paint, followed by drying and a heat treatment at 100 °. vs.
  • This polymeric compound also makes it possible to obtain adherent conductive deposits whose conductivity is stable in air on plastics treated by the Corona effect.
  • Example 65 Poly (2- [2- (3-thienyl) ethoxy] -ethanesulfonyl (trifluoromethanesulfonyl) imide)
  • the polyaniline doped with trifluoromethanesulfonyl (di-2-ethylhexylaminosulfonyl) imide was recovered. In this form, it is soluble in toluene.
  • a toluene solution of the doped polyaniline was used to make a film which is an electronic conductive polymer whose conductivity, measured by the four-point method, is 6 S / cm, with good stability in a humid environment.
  • a film was also produced from this solution on a polypropylene (PP) support treated with the Corona effect. After drying under vacuum at 60 ° C for 48 hours, a conductive and adherent deposit of polyaniline with a thickness less than one micron was obtained. This type of treatment on plastics is particularly interesting to carry out by electrical contactors flexible or electromagnetic protection systems.
  • Example 67 Poly (4-styrenesulfonyl (trifluroro methane sulfonyl) imide) 20.62 g of poly (sodium 4-styrenesulfonate) having a weight average mass of 10 6 g / mole (100 mmol of -S0 3 Na), (marketed by Aldrich) suspended in 100 ml of anhydrous dimethylformamide were treated with 14.08 g (110 mmol) of (chloromethylene) dimethylammonium chloride
  • the corresponding lithium salt was prepared quantitatively by ion exchange (metathesis) between the potassium salt and the lithium chloride in anhydrous tetrahydrofuran.
  • This polyelectrolyte is soluble in most common organic solvents (tetrahydrofuran, acetonitrile, dimethylformamide, ethyl acetate, glymes) and in polar polymers. By using a suitable cation, this poyelectrolyte can be a dopant of conjugated electronic conductive polymers such as polypyrrole or polyaniline.
  • EXAMPLE 68 Catalysis of Aldolic Condensation
  • the diethylaminosulfonyl (trifluoromethanesulfonyl) imide was prepared from its potassium salt, obtained in Example 28, according to a process similar to that used in Example 29 to obtain dimethylaminosulfonyl ( trifluoromethane-sulfonyl) imide. Subsequently, 2.84 g of this acid (10 mmol) was treated with 657 mg of ytterbium oxide Yb 2 0 3 (1.67 mmol) in 20 ml of water. After 24 hours with stirring, the solution was lyophilized, then the product obtained dried under vacuum for 48 hours at 60 ° C. The ytterbium salt of diethylaminosulfonyl (trifluoromethanesulfonyl) imide (Yb (DETFSI) 3 ) was obtained quantitatively.
  • This salt was used as a catalyst for an aldolic condensation reaction in the following manner:
  • the ytterbium salt of diethylaminosulfonyl- (trifluoromethanesulfonyl) imide, obtained in Example 40, was used as catalyst in a Michael addition as follows: A 410 mg of Yb (DETFSI) 3 (0.4 mmol , 10 mol%), obtained in Example 65, in 15 ml of dichloromethane, a mixture of 1.05 g of l-ene-2-methyl-1-silylacetal-1-methoxypropene (CH 3 ) was added 2 C C (OSiMe 3 ) OMe (6 mmol) and 840 mg of chalcone (4 mmol) in 10 ml of dichloromethane.
  • Example 70 Catalysis of a Friedel-Crafts acylation reaction at 10 ml of a 1 M solution of triethylaluminum (C 2 H) 3 A1 (10 mmol) (sold by Aldrich) 2.84 g of trifluoromethanesulfonyl (diethylamino-sulfonyl) imide (C 2 H 5 ) 2 NS0 2 NHS0 2 CF 3 (10 mmol) dissolved in 10 ml of toluene, designated toluene, are slowly added under argon under argon -after by HDETFSI, prepared beforehand from the corresponding potassium salt by extraction with ether.
  • C 2 H 3 A1 sold by Aldrich
  • Example 71 Catalysis of a Diels Reaction & Help Various salts according to the invention were used as catalysts for a Diels reaction Help, namely the reaction of methylvinylketone with cyclopentadiene.
  • the salts used are the lanthanum salt of trifluoromethanesulfonyl (R (-) -1-phenyl- 2, 2, 2-trifluoroethanoxysulfonyl) imide (LaPTETFSI) prepared in accordance with Example 46, the lanthanum salt of (1R) - (-) -10-camphor-sulfonyl (perfluorobutanesulfonyl) imide (LaCSTFSI) prepared according to Example 48, the lanthanum salt of (1R) - (-) -trifluoromethanesulfonyl (N-Methoxybutyl-
  • Example 72 Acrylonitrile / 4-styrenesulfonyl (trifluoromethanesulfonyl) imide copolymer
  • This polymer can be used for the preparation of gelled polymer electrolytes with fixed anions, the polymer ensuring the dual functionality of matrix making it possible to obtain the gel and polyelectrolytes.
  • a gelled electrolyte consisting of 30% by weight of the polyelectrolyte, 35% ethylene carbonate and 35% propylene carbonate was prepared. This gel has good mechanical properties and a conductivity of 9.6.10 -4 S. cm -1 at 30 ° C. The number of cationic transport in this electrolyte is 0.85.
  • An electrochemical generator was assembled comprising an anode constituted by carbon coke (80% by volume) mixed with the copolymer (PANSDTFSI) as binder (20% by volume),
  • Example 73 Acrylonitrile / 4-styrenesulfonyl (trifluoromethanesulfonyl) imide copolymer According to a process similar to that used in Example 76, a copolymer of acrylonitrile (3 mol%) and the lithium salt of 4-styrenesulfonyl was synthesized. (trifluoromethanesulfonyl) - imide (97 mol%).
  • This copolymer has antistatic properties, unlike polyacrylonitrile (PAN) which, in the form of the alkali or ammonium salt, is widely used in the form of fiber for textiles.
  • PAN polyacrylonitrile
  • the spinning of this copolymer is easier than that of the unmodified PAN.
  • the copolymer has very good interactions with cationic dyes such as methylene blue, which makes it a material of interest for colored textile fibers. The stability of the color being markedly improved compared to the conventional copolymer of acrylonitrile and methallylsulfonate.
  • This polymer makes it possible to produce gelled polymer electrolytes with fixed anions, the polymer ensuring the dual functionality of matrix allowing the gel and polyelectrolytes to be obtained.
  • Example 75 Copolymer AGE / Epoxy-demiTFSI / OE
  • a solution was introduced in 100 ml of anhydrous tetrahydrofuran of 15.37 g (50 mmol) of the potassium salt of 3,4-epoxybutane-1-sulfonyl (trifluoromethanesulfonyl) imide, prepared as in Example 13, and 685 mg (6 mmol) of allylglycidylether.
  • This polymer makes it possible to produce polymeric or gelled electrolytes with fixed anions, the polymer ensuring the dual functionality of matrix making it possible to obtain the gel and polyelectrolytes. It can be crosslinked during the manufacturing process of the electrochemical system that contains it.
  • This polymer is soluble in most organic solvents, including at contents> 2% in oils or silicone materials, thus giving them antistatic properties.
  • Example 77 Li / POE / V battery 2 0 5
  • the assembly was then extruded at a temperature of 100 ° C. in the form of a strip 14 cm wide and a thickness of 63 ⁇ m. This film, usable as a cathode, was directly deposited on a sheet of stainless steel 8 ⁇ m thick.
  • the salts of the present invention containing long alkyl chains such as the potassium salt of Igepal® CA-520-propylsulfonyl (trifluoromethanesulfonyl) imide or the lithium salt of dodecylsulfonyl (trifluoromethanesulfonyl) imide, make it possible to plasticize the poly (ethylene oxide). They thus make it easier to extrude the cathode or electrolyte films used during the manufacture of batteries according to the lithium-polymer thin film technology. Their electrochemical stability also makes it possible to obtain good performance when cycling these batteries. CLAIMS
  • Ionic compound constituted by an amide or one of its salts, comprising an anionic part associated with at least one cationic part M + m in sufficient number to ensure the electronic neutrality of the whole, characterized in that M is a hydroxonium, nitrosonium N0 + , ammonium -NH 4 + , a metal cation having the valence m, an organic cation having the valence m or an organometallic cation having the valence m and in that the anionic part corresponds to the formula R F -SO x -N ⁇ -Z in which: the group -S (0) x - represents a sulfonyl group -S0 2 - or a sulfinyl group -SO-; - R F is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding
  • Z represents an electron-attracting radical having a Hammett parameter at least equal to that of a phenyl radical, chosen from: j) -CN, -N02, -SCN, -Ns, -CF 3 , R ' F CH 2 - (R ′ F being a perfluorinated radical), fluoroalkyloxy radicals, fluoroalkylthioxy radicals, jj) radicals comprising one or more aromatic rings optionally containing at least one nitrogen, oxygen, sulfur or phosphorus atom, said rings possibly being condensed nuclei and / or said nuclei possibly carrying at least one substituent chosen from halogens, -CN,

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US09/125,797 US6319428B1 (en) 1996-12-30 1997-12-30 Perfluorinated amide salts and their uses as ionic conducting materials
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CA2248303A CA2248303C (fr) 1996-12-30 1997-12-30 Sels d'amides perfluores, et leurs utilisations comme materiaux a conduction ionique
US10/253,035 US20030052310A1 (en) 1996-12-30 2002-09-24 Perfluorinated amide salts and their uses as ionic conducting materials
US10/789,453 US20050074668A1 (en) 1996-12-30 2004-02-27 Perfluorinated amide salts and their uses as ionic conducting materials
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002508576A (ja) * 1998-03-24 2002-03-19 ミネソタ マイニング アンド マニュファクチャリング カンパニー 混合フルオロカーボン／炭化水素イミド塩およびメチド塩を含有する電解質
WO2002072519A3 (en) * 2001-03-12 2002-11-21 Univ Belfast Process catalysed by fluoroalkylsulfonated compounds, preferably bis-triflimide compounds
JP2003532619A (ja) * 1998-08-25 2003-11-05 ミネソタ マイニング アンド マニュファクチャリング カンパニー スルホニルイミドおよび導電性塩としてのその使用
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962546A (en) † 1996-03-26 1999-10-05 3M Innovative Properties Company Cationically polymerizable compositions capable of being coated by electrostatic assistance
JP4823401B2 (ja) * 1996-12-30 2011-11-24 イドロ―ケベック 過フッ化アミド塩及びイオン伝導物質としてのその使用方法
WO1999005100A1 (fr) 1997-07-25 1999-02-04 Acep Inc Composes ioniques ayant une charge anionique delocalisee, leur utilisation comme composants de conducteurs ioniques ou de catalyseur
WO1999005126A1 (fr) 1997-07-25 1999-02-04 Acep Inc. Composes ioniques perfluorovinyliques et leur utilisation dans des materiaux conducteurs
CA2215849A1 (en) * 1997-09-11 1999-03-11 Christophe Michot New solvent and electrolytic composition with high conductivity and wide stability range
WO1999028292A1 (fr) * 1997-12-01 1999-06-10 Acep Inc. Sels de sulfones perfluores, et leurs utilisations comme materiaux a conduction ionique
GB9726008D0 (en) * 1997-12-10 1998-02-04 Secr Defence Eletrolyte
JP4417554B2 (ja) * 1998-03-03 2010-02-17 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 相当にフッ素化されたイオノマー
FR2781932B1 (fr) * 1998-07-10 2000-09-01 Giat Ind Sa Electrolyte solide polymere et ses procedes de preparation
US6294289B1 (en) * 1998-08-25 2001-09-25 3M Innovative Properties Company Cyano-substituted methide and amide salts
DE19858925A1 (de) 1998-12-19 2000-06-21 Aventis Res & Tech Gmbh & Co Elektrolytsystem für Lithiumbatterien und dessen Verwendung sowie Verfahren zur Erhöhung der Sicherheit von Lithiumbatterien
EP1033731B1 (en) * 1999-03-01 2006-07-05 Fuji Photo Film Co., Ltd. Photo-electrochemical cell containing an electrolyte comprising a liquid crystal compound
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US6765115B1 (en) * 1999-11-23 2004-07-20 E.I. Du Pont De Nemours And Company Method for preparing dimetal sulfonyl amide salts
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EP1237858B1 (en) 1999-12-02 2004-07-14 E.I. Du Pont De Nemours And Company Method for preparing imides from sulfonyl fluorides
US6692658B2 (en) * 1999-12-17 2004-02-17 Canon Kabushiki Kaisha Electrolyte and secondary cell
SG83222A1 (en) * 1999-12-27 2001-09-18 Sumitomo Chemical Co Catalyst component for addition polymerization, catalyst for addition polymerization, and process for producing addition polymer
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US6522522B2 (en) * 2000-02-01 2003-02-18 Cabot Corporation Capacitors and supercapacitors containing modified carbon products
DE10004928A1 (de) * 2000-02-04 2001-08-09 Solvay Fluor & Derivate Verwendung von Amidinen
US20040082464A1 (en) * 2000-03-31 2004-04-29 Romano Anna Maria Complex polymerization catalysts for the homopolymerization of ethylene and for the copolymerization of ethylene
US7220914B2 (en) * 2003-12-01 2007-05-22 Konarka Technologies, Inc. Zwitterionic compounds and photovoltaic cells containing same
JP4682395B2 (ja) * 2000-04-28 2011-05-11 日産自動車株式会社 非水電池
DE10023744A1 (de) * 2000-05-15 2001-12-13 Bayer Ag Elektrochrome Anzeigevorrichtung mit hoher Kantenschärfe
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JP2002134113A (ja) * 2000-10-30 2002-05-10 Matsushita Electric Ind Co Ltd 非水系二次電池
US6841303B2 (en) * 2001-01-17 2005-01-11 Skc Co., Ltd. High ionic conductivity gel polymer electrolyte for rechargeable polymer batteries
US7253289B2 (en) * 2001-01-22 2007-08-07 Covalent Associates, Inc. One-step process for the preparation of halide-free hydrophobic salts
JP3969077B2 (ja) * 2001-04-04 2007-08-29 住友化学株式会社 高分子電解質及びその製造方法
US20030054172A1 (en) * 2001-05-10 2003-03-20 3M Innovative Properties Company Polyoxyalkylene ammonium salts and their use as antistatic agents
JP4752135B2 (ja) * 2001-05-25 2011-08-17 株式会社Ｇｓユアサ リチウム電池
JP4222466B2 (ja) * 2001-06-14 2009-02-12 富士フイルム株式会社 電荷輸送材料、それを用いた光電変換素子及び光電池、並びにピリジン化合物
JP4287741B2 (ja) * 2001-06-22 2009-07-01 アグフア−ゲヴエルト，ナームローゼ・フエンノートシヤツプ 伝導性パターンを有する材料；ならびに伝導性パターンの形成のための材料及び方法
US6746751B2 (en) 2001-06-22 2004-06-08 Agfa-Gevaert Material having a conductive pattern and a material and method for making a conductive pattern
US6545109B2 (en) 2001-06-29 2003-04-08 3M Innovative Properties Company Imide salts as emulsifiers for the polymerization of fluoroolefins
WO2003011958A1 (en) * 2001-08-02 2003-02-13 3M Innovative Properties Company Optically clear and antistatic pressure sensitive adhesives
JP4036279B2 (ja) * 2001-10-09 2008-01-23 よこはまティーエルオー株式会社 プロトン伝導体及びこれを用いた燃料電池
US7241535B2 (en) * 2001-10-15 2007-07-10 Samsung Sdi Co., Ltd. Electrolyte for lithium-sulfur batteries and lithium-sulfur batteries comprising the same
JP4004769B2 (ja) * 2001-10-17 2007-11-07 Ｎｅｃトーキン株式会社 電解液、並びにこれを用いた電気化学セル
DE10155281A1 (de) * 2001-11-08 2003-06-05 Solvent Innovation Gmbh Verfahren zur Entfernung polarisierbarer Verunreinigungen aus Kohlenwasserstoffen und Kohlenwasserstoffgemischen durch Extraktion mit ionischen Flüssigkeiten
US7303852B2 (en) * 2001-12-27 2007-12-04 Shin-Etsu Chemical Co., Ltd. Photoacid generating compounds, chemically amplified positive resist materials, and pattern forming method
CA2474484C (en) * 2002-01-25 2013-03-26 Powermers, Inc. Polymer-modified electrode for energy storage devices and electrochemical supercapacitor based on said polymer-modified electrode
US20030153094A1 (en) * 2002-02-13 2003-08-14 Board Of Trustees Of Michigan State University Conductimetric biosensor device, method and system
CN1678948A (zh) * 2002-03-27 2005-10-05 艾利丹尼森公司 可转换的电－光层压制品
TWI263235B (en) 2002-04-02 2006-10-01 Nippon Catalytic Chem Ind Material for electrolytic solutions and use thereof
US6803152B2 (en) * 2002-04-19 2004-10-12 Ener1 Battery Company Nonaqueous electrolytes based on organosilicon ammonium derivatives for high-energy power sources
US7709158B1 (en) 2002-05-09 2010-05-04 Electrochem Solutions, Inc. Guanidine derivatives as cations for ambient temperature molten sales in electrochemical power sources
US20030211389A1 (en) * 2002-05-09 2003-11-13 Schlaikjer Carl R. Guanidine derivatives as cations for ambient temperature molten salts in electrochemical power sources
US7042615B2 (en) 2002-05-17 2006-05-09 The Regents Of The University Of California Electrochromic devices based on lithium insertion
CN100339913C (zh) * 2002-05-23 2007-09-26 哥伦比亚化学公司 用于燃料电池的、磺化导电聚合物接枝的碳材料
EP1509929A4 (en) * 2002-05-23 2007-03-21 Columbian Chem LINE COUNTERPOLYMER CARBON MATERIAL FOR FUEL CELL APPLICATIONS
US7390441B2 (en) * 2002-05-23 2008-06-24 Columbian Chemicals Company Sulfonated conducting polymer-grafted carbon material for fuel cell applications
US7241334B2 (en) * 2002-05-23 2007-07-10 Columbian Chemicals Company Sulfonated carbonaceous materials
US7459103B2 (en) * 2002-05-23 2008-12-02 Columbian Chemicals Company Conducting polymer-grafted carbon material for fuel cell applications
JP2004031423A (ja) * 2002-06-21 2004-01-29 Nissan Diesel Motor Co Ltd グローブボックス装置
US7763186B2 (en) * 2002-06-21 2010-07-27 Los Alamos National Security, Llc Preparation and purification of ionic liquids and precursors
EP1529240A4 (en) * 2002-06-21 2008-04-16 Univ California ELECTROLYTE FOR ELECTRIC OPTICAL EQUIPMENT WITH IONIC LIQUIDS
KR100463181B1 (ko) * 2002-07-12 2004-12-23 삼성에스디아이 주식회사 리튬-설퍼 전지용 전해액 및 이를 포함하는 리튬-설퍼 전지
US20040038127A1 (en) * 2002-08-20 2004-02-26 Schlaikjer Carl Roger Small cation/delocalizing anion as an ambient temperature molten salt in electrochemical power sources
JP2004082365A (ja) * 2002-08-23 2004-03-18 Fuji Photo Film Co Ltd 感熱記録材料
US7317047B2 (en) 2002-09-24 2008-01-08 E.I. Du Pont De Nemours And Company Electrically conducting organic polymer/nanoparticle composites and methods for use thereof
AU2003275203A1 (en) 2002-09-24 2004-04-19 E.I. Du Pont De Nemours And Company Water dispersible polythiophenes made with polymeric acid colloids
JP4464277B2 (ja) 2002-09-24 2010-05-19 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法
CA2499364A1 (en) 2002-09-24 2004-04-08 E. I. Du Pont De Nemours And Company Water dispersible polyanilines made with polymeric acid colloids for electronics applications
EP1406336A1 (en) * 2002-10-01 2004-04-07 Xoliox SA Electrolyte composition having improved aluminium anticorrosive properties
KR101015647B1 (ko) * 2002-11-22 2011-02-22 닛뽕 카릿또 가부시키가이샤 근적외선 흡수색소 및 근적외선 차단필터
EP1528580B2 (en) † 2003-01-15 2015-07-01 Nippon Shokubai Co., Ltd. Dye-sensitized type solar cell
US20040149472A1 (en) * 2003-02-03 2004-08-05 Warner Benjamin P. Radiofrequency attenuator and method
JP2004265638A (ja) * 2003-02-25 2004-09-24 Ebara Corp 混合伝導カーボンおよび電極
US7390438B2 (en) 2003-04-22 2008-06-24 E.I. Du Pont De Nemours And Company Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids
US7312100B2 (en) * 2003-05-27 2007-12-25 The North Carolina State University In situ patterning of electrolyte for molecular information storage devices
WO2005001979A2 (en) * 2003-06-27 2005-01-06 E.I. Dupont De Nemours And Company Fluorinated sulfonamide compounds and polymer electrolyte membranes pepared therefrom for use in electrochemical cells
EP1646054A4 (en) * 2003-07-11 2010-05-19 Ube Industries ACIDS-BASE MIXTURE AND ION CONDUCTOR COMPOSED FROM SUCH A MIXTURE
US7001936B2 (en) * 2003-07-16 2006-02-21 Lexmark International, Inc. Pigmented inkjet ink
EP1673830A2 (en) * 2003-09-30 2006-06-28 Honeywell International Inc. Electrolyte with indicator
US7074491B2 (en) * 2003-11-04 2006-07-11 Dionex Corporation Polar silanes for binding to substrates and use of the bound substrates
US8828610B2 (en) * 2004-01-06 2014-09-09 Sion Power Corporation Electrolytes for lithium sulfur cells
US10297827B2 (en) 2004-01-06 2019-05-21 Sion Power Corporation Electrochemical cell, components thereof, and methods of making and using same
US10629947B2 (en) 2008-08-05 2020-04-21 Sion Power Corporation Electrochemical cell
US7358012B2 (en) 2004-01-06 2008-04-15 Sion Power Corporation Electrolytes for lithium sulfur cells
TWI302760B (en) 2004-01-15 2008-11-01 Lg Chemical Ltd Electrochemical device comprising aliphatic nitrile compound
JP4433165B2 (ja) * 2004-02-16 2010-03-17 ソニー株式会社 カチオン伝導体およびこれを用いた電気化学デバイス
JP4507629B2 (ja) * 2004-02-20 2010-07-21 東洋インキ製造株式会社 樹脂グラフトカーボンブラック組成物
WO2005083159A2 (en) * 2004-02-23 2005-09-09 E.I. Dupont De Nemours & Company Apparatus adapted for membrane mediated electropolishing
US7351358B2 (en) 2004-03-17 2008-04-01 E.I. Du Pont De Nemours And Company Water dispersible polypyrroles made with polymeric acid colloids for electronics applications
US7785740B2 (en) * 2004-04-09 2010-08-31 Air Products And Chemicals, Inc. Overcharge protection for electrochemical cells
US8147962B2 (en) 2004-04-13 2012-04-03 E. I. Du Pont De Nemours And Company Conductive polymer composites
TW200606970A (en) 2004-05-10 2006-02-16 Nippon Catalytic Chem Ind Material for electrolytic solution, ionic material-containing composition and use thereof
US7960057B2 (en) * 2004-05-17 2011-06-14 Toyota Motor Engineering & Manufacturing North America, Inc. Battery with molten salt electrolyte and phosphorus-containing cathode
US20050287441A1 (en) * 2004-06-23 2005-12-29 Stefano Passerini Lithium polymer electrolyte batteries and methods of making
JP2006008454A (ja) * 2004-06-25 2006-01-12 Fuji Xerox Co Ltd 炭素微粒子構造体とその製造方法、およびこれを製造するための炭素微粒子転写体と炭素微粒子構造体製造用溶液、並びに炭素微粒子構造体を用いた炭素微粒子構造体電子素子とその製造方法、そして集積回路
JP4731132B2 (ja) * 2004-06-29 2011-07-20 株式会社Ａｄｅｋａ 非水電解液及び該電解液を用いた非水電解液二次電池
JP4412598B2 (ja) * 2004-07-20 2010-02-10 第一工業製薬株式会社 イオンポリマーゲル電解質およびその前駆体組成物
AU2004240178A1 (en) * 2004-08-20 2006-03-09 Commonwealth Scientific And Industrial Research Organisation Zwitterionic additives for electrochemical devices
EP1634867A1 (de) * 2004-08-25 2006-03-15 Lonza AG Tricyanomethansalze organischer Kationen
EP1796193B1 (en) * 2004-09-03 2011-12-14 Nissan Motor Co., Ltd. Proton conductor and fuel cell using the same
KR100663032B1 (ko) * 2004-09-21 2006-12-28 주식회사 엘지화학 공융혼합물을 포함하는 전해질 및 이를 이용한 전기 변색소자
US20060068987A1 (en) * 2004-09-24 2006-03-30 Srinivas Bollepalli Carbon supported catalyst having reduced water retention
JP4709518B2 (ja) * 2004-09-29 2011-06-22 株式会社東芝 プロトン伝導膜及び燃料電池
WO2006063441A1 (en) * 2004-12-13 2006-06-22 Transfert Plus, S.E.C. Compositions, redox couples and uses thereof
FR2879458B1 (fr) * 2004-12-21 2007-07-20 Centre Nat Rech Scient Cnrse Sulfamides et sulfinimides fluores
AU2006205076B2 (en) 2005-01-10 2010-12-23 Avery Dennison Corporation Removable curl labels
KR100616666B1 (ko) 2005-01-27 2006-08-28 삼성전기주식회사 카본나노튜브에 구아니딘기를 형성하는 방법,구아니딘기가 형성된 카본나노튜브를 기판에 부착하는방법 및 이에 따라 제조된 카본나노튜브 및 기판
WO2006088033A1 (ja) * 2005-02-17 2006-08-24 Kaneka Corporation 金属表面コーティング用組成物、導電性高分子の製造方法、金属表面のコーティング方法、ならびに電解コンデンサおよびその製造方法
JP2006257288A (ja) * 2005-03-17 2006-09-28 Kaneka Corp 金属表面コーティング用組成物、導電性高分子の製造方法、金属表面のコーティング方法、ならびに電解コンデンサおよびその製造方法
JP4856883B2 (ja) * 2005-03-03 2012-01-18 富士フイルム株式会社 機能性素子、エレクトロクロミック素子、光学デバイス及び撮影ユニット
DE102005013790B4 (de) * 2005-03-24 2007-03-29 Polymaterials Ag Polymerelektrolyt, Verwendung des Polymerelektrolyten und elektrochemische Vorrichtung, die den Polymerelektrolyten umfasst
CA2506104A1 (en) * 2005-05-06 2006-11-06 Michel Gauthier Surface modified redox compounds and composite electrode obtain from them
US7619803B2 (en) * 2005-05-31 2009-11-17 Konica Minolta Holdings, Inc. Electrochromic display element and full-color electrochromic display element
US7579184B2 (en) * 2005-06-02 2009-08-25 Board Of Trustees Of Michigan State University Methods to increase dynamic range and improve quantitative analysis in rapid biosensors
WO2007002740A2 (en) 2005-06-28 2007-01-04 E. I. Du Pont De Nemours And Company Buffer compositions
KR101356296B1 (ko) * 2005-06-28 2014-02-06 이 아이 듀폰 디 네모아 앤드 캄파니 높은 일 함수의 투명한 도체
WO2007022624A1 (en) * 2005-08-22 2007-03-01 Transfert Plus, S.E.C. Process for preparing sulfonylimides and derivatives thereof
WO2007049922A1 (en) 2005-10-27 2007-05-03 Lg Chem, Ltd. Secondary battery comprising eutectic mixture and preparation method thereof
WO2007055392A1 (en) * 2005-11-11 2007-05-18 Nippon Shokubai Co., Ltd. Ionic compound
WO2007068822A2 (fr) * 2005-12-12 2007-06-21 Phostech Lithium Inc. Sels de sulfonyl-1, 2, 4-triazole
WO2008005055A2 (en) * 2005-12-29 2008-01-10 The Board Of Trustees Of The University Of Illinois Nanoparticles containing titanium oxide
WO2007117332A2 (en) * 2005-12-29 2007-10-18 The Board Of Trustees Of The University Of Illinois Titanium oxide base photocatalysts
US8216680B2 (en) * 2006-02-03 2012-07-10 E I Du Pont De Nemours And Company Transparent composite conductors having high work function
JP4682057B2 (ja) * 2006-02-20 2011-05-11 富士フイルム株式会社 感光性組成物、該感光性組成物を用いたパターン形成方法及び該感光性組成物に用いられる化合物
US20090045373A1 (en) * 2006-03-10 2009-02-19 Amer Hammami Compounds, ionic liquids, molten salts and uses thereof
JP5683104B2 (ja) * 2006-03-21 2015-03-11 ノヴァレッド・アクチエンゲゼルシャフト ドープされた有機半導体材料の製造方法及びそのために用いられる配合物
DE112007000789B4 (de) * 2006-03-30 2012-03-15 Novaled Ag Verwendung von Bora-tetraazepentalenen
US8268197B2 (en) * 2006-04-04 2012-09-18 Seeo, Inc. Solid electrolyte material manufacturable by polymer processing methods
WO2007142731A2 (en) 2006-04-04 2007-12-13 The Regents Of The University Of California High elastic modulus polymer electrolytes
US7696122B2 (en) * 2006-07-05 2010-04-13 Cabot Corporation Electrocatalyst inks for fuel cell applications
US20080214814A1 (en) * 2006-07-18 2008-09-04 Zaiwei Li Stable ionic liquid complexes and methods for determining stability thereof
KR101375675B1 (ko) * 2006-07-27 2014-03-19 니치콘 가부시키가이샤 이온성 화합물
EP1903029A1 (de) * 2006-08-16 2008-03-26 Lonza Ag Verfahren zur Herstellung von Alkali- oder Erdalkalimetalltricyanomethaniden
US20100092864A1 (en) * 2006-08-17 2010-04-15 Mitsubishi Chemical Corporation Negative-electrode active material for lithium ion secondary battery, process for producing the same, and negative electrode for lithium ion secondary battery and lithium ion secondary battery both employing the same
US7820323B1 (en) 2006-09-07 2010-10-26 The United States Of America As Represented By The Secretary Of The Army Metal borate synthesis process
US7833660B1 (en) 2006-09-07 2010-11-16 The United States Of America As Represented By The Secretary Of The Army Fluorohaloborate salts, synthesis and use thereof
CN101563432B (zh) 2006-11-02 2014-12-03 艾利丹尼森公司 用于可洗膜的乳液粘合剂
EP2081082A4 (en) * 2006-11-08 2010-12-08 Konica Minolta Holdings Inc DISPLAY ELEMENT
US7864397B2 (en) * 2006-12-04 2011-01-04 3M Innovative Properties Company Curable electrolyte
US8043418B2 (en) * 2006-12-08 2011-10-25 General Electric Company Gas separator apparatus
KR100767427B1 (ko) * 2006-12-21 2007-10-17 제일모직주식회사 리튬 2차전지용 비수성 전해액 및 이를 포함하는 리튬2차전지
US20080191172A1 (en) 2006-12-29 2008-08-14 Che-Hsiung Hsu High work-function and high conductivity compositions of electrically conducting polymers
JP5110625B2 (ja) * 2007-02-02 2012-12-26 パナソニック株式会社 蓄電デバイス
US7820347B1 (en) * 2007-02-06 2010-10-26 The United States Of America As Represented By The Secretary Of The Air Force Conversion of salt halides to nitrate salts
JP2010518581A (ja) * 2007-02-06 2010-05-27 スリーエム イノベイティブ プロパティズ カンパニー 新規結合剤を含む電極、並びにその製造方法及び使用方法
US7875388B2 (en) 2007-02-06 2011-01-25 3M Innovative Properties Company Electrodes including polyacrylate binders and methods of making and using the same
US8540899B2 (en) 2007-02-07 2013-09-24 Esionic Es, Inc. Liquid composite compositions using non-volatile liquids and nanoparticles and uses thereof
US8012277B2 (en) * 2007-04-13 2011-09-06 Alliant Techsystems Inc. Ionic liquid and a method of synthesizing an ionic liquid
CN101657522B (zh) * 2007-04-13 2014-05-07 3M创新有限公司 防静电光学透明的压敏粘合剂
JP2008266155A (ja) * 2007-04-17 2008-11-06 Asahi Kasei Corp スルホンイミドリチウム塩の製造方法
CN101730724A (zh) * 2007-04-24 2010-06-09 太阳化学公司 用于非水性油墨和涂料的颜料
US8241526B2 (en) * 2007-05-18 2012-08-14 E I Du Pont De Nemours And Company Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives
US8287810B2 (en) * 2007-06-20 2012-10-16 Board Of Trustees Of Michigan State University Electrically-active ferromagnetic particle conductimetric biosensor test kit
KR101451802B1 (ko) * 2007-07-31 2014-10-16 삼성에스디아이 주식회사 글리시딜 에테르계 화합물을 채용한 유기전해액 및 리튬전지
KR20100057065A (ko) * 2007-08-16 2010-05-28 론자 리미티드 알칼리 금속 및 알칼리 토금속 트리시아노메타니드의 제조 및 정제방법
WO2009089018A2 (en) * 2008-01-08 2009-07-16 Sion Power Corporation Porous electrodes and associated methods
JP4936069B2 (ja) * 2007-10-31 2012-05-23 株式会社デンソー モータ制御装置
US20090122389A1 (en) 2007-11-14 2009-05-14 E Ink Corporation Electro-optic assemblies, and adhesives and binders for use therein
US20090181441A1 (en) * 2007-11-27 2009-07-16 Board Of Trustees Of Michigan State University Porous silicon-polymer composites for biosensor applications
WO2009069757A1 (ja) * 2007-11-30 2009-06-04 Fujikura Ltd. 電解質組成物およびこれを用いた光電変換素子
FR2925181B1 (fr) * 2007-12-12 2010-09-10 Hydro Quebec Lentille optique electrochrome
KR101509278B1 (ko) * 2007-12-27 2015-04-06 도까이 카본 가부시끼가이샤 표면 처리 카본 블랙 수성 분산체와 그 제조 방법
WO2009092058A1 (en) * 2008-01-16 2009-07-23 Seeo, Inc Gel polymer electrolytes for batteries
KR101013328B1 (ko) * 2008-01-18 2011-02-09 주식회사 엘지화학 공융혼합물을 포함하는 전해질 및 이를 구비한전기화학소자
US8034485B2 (en) 2008-05-29 2011-10-11 3M Innovative Properties Company Metal oxide negative electrodes for lithium-ion electrochemical cells and batteries
US9782949B2 (en) 2008-05-30 2017-10-10 Corning Incorporated Glass laminated articles and layered articles
JP5471036B2 (ja) * 2008-06-05 2014-04-16 ソニー株式会社 マグネシウムイオン含有非水電解液及びこれを用いた電気化学デバイス
US7715082B2 (en) * 2008-06-30 2010-05-11 Soladigm, Inc. Electrochromic devices based on lithium insertion
JP2010047751A (ja) * 2008-07-24 2010-03-04 Sumitomo Chemical Co Ltd イオン交換ポリマー
FR2935382B1 (fr) * 2008-08-29 2010-10-08 Centre Nat Rech Scient Sel d'anion pentacylique et son utilisation comme electrolyte
JP4444355B2 (ja) * 2008-09-03 2010-03-31 株式会社東芝 燃料電池
US7951525B2 (en) * 2008-09-08 2011-05-31 International Business Machines Corporation Low outgassing photoresist compositions
US8129448B2 (en) * 2008-12-18 2012-03-06 Cabot Corporation Method of preparing polymer modified pigments
US20100193449A1 (en) * 2009-02-02 2010-08-05 Jian-Ku Shang Materials and methods for removing arsenic from water
EP2406796A2 (en) 2009-03-12 2012-01-18 E. I. du Pont de Nemours and Company Electrically conductive polymer compositions for coating applications
ES2929654T3 (es) 2009-03-30 2022-11-30 Avery Dennison Corp Etiqueta adhesiva despegable que contiene una capa de película polimérica de alto módulo de tracción
EP2414473B1 (en) 2009-03-30 2014-12-31 Avery Dennison Corporation Removable adhesive label containing inherently shrinkable polymeric film
ES2622956T3 (es) 2009-03-30 2017-07-10 Avery Dennison Corporation Etiqueta adhesiva retirable que contiene una capa de película polimérica que tiene afinidad por el agua
US9664974B2 (en) 2009-03-31 2017-05-30 View, Inc. Fabrication of low defectivity electrochromic devices
FR2944149B1 (fr) * 2009-04-06 2011-04-29 Centre Nat Rech Scient Electrode composite.
CN102395628B (zh) 2009-04-21 2016-01-20 E.I.内穆尔杜邦公司 导电聚合物组合物和由其制得的膜
JP2012524834A (ja) 2009-04-24 2012-10-18 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 導電性ポリマー組成物およびそれから作製されたフィルム
JP5645459B2 (ja) * 2009-07-10 2014-12-24 富士フイルム株式会社 感活性光線性または感放射線性樹脂組成物およびこれを用いたパターン形成方法
WO2011031297A2 (en) 2009-08-28 2011-03-17 Sion Power Corporation Electrochemical cells comprising porous structures comprising sulfur
EP2314572A1 (de) 2009-10-20 2011-04-27 Philipps-Universität Marburg Lithiumsalze von Pentafluorphenylamid-Anionen, ihre Herstellung und ihre Verwendung
WO2011056895A1 (en) * 2009-11-03 2011-05-12 University Of Notre Dame Du Lac Ionic liquids comprising heteraromatic anions
TW201117245A (en) * 2009-11-11 2011-05-16 Taiwan Textile Res Inst Water-based electrolyte for electric double layer capacitor and electric double layer capacitor having the same
JP5629510B2 (ja) * 2009-11-30 2014-11-19 大日本印刷株式会社 トリアリールメタン系染料
KR101311933B1 (ko) * 2009-12-29 2013-09-27 제일모직주식회사 전도성 고분자 중합체, 전도성 고분자 조성물, 전도성 고분자 조성물막 및 이를 이용한 유기광전소자
US8730649B2 (en) 2010-03-12 2014-05-20 Taiwan Textile Research Institute Aqueous electrolyte solution for electric double-layer capacitor and electric double-layer capacitor having the same
JP2011198508A (ja) * 2010-03-17 2011-10-06 Sony Corp リチウム二次電池、リチウム二次電池用電解液、電動工具、電気自動車および電力貯蔵システム
KR101346977B1 (ko) 2010-06-04 2014-01-02 주식회사 엘지화학 하이드로포르밀화 반응 부산물 제거용 장치 및 방법
KR20130105838A (ko) 2010-08-24 2013-09-26 바스프 에스이 전기화학 셀용 전해질 물질
JP5398801B2 (ja) * 2010-10-29 2014-01-29 旭化成株式会社 高分子電解質
US8828346B2 (en) 2011-03-08 2014-09-09 Trinapco, Inc. Method of making fluorosulfonylamine
JP5673258B2 (ja) * 2011-03-17 2015-02-18 大日本印刷株式会社 カラーフィルター用着色組成物及びそれを用いたカラーフィルター、並びに表示装置
US8859297B2 (en) 2011-05-23 2014-10-14 Board Of Trustees Of Michigan State University Detection of conductive polymer-labeled analytes
US8735002B2 (en) 2011-09-07 2014-05-27 Sion Power Corporation Lithium sulfur electrochemical cell including insoluble nitrogen-containing compound
EP2721665B1 (en) 2011-06-17 2021-10-27 Sion Power Corporation Plating technique for electrode
JP6060478B2 (ja) * 2011-08-03 2017-01-18 住友化学株式会社 化合物及びその製造方法
JP5268123B2 (ja) * 2011-08-26 2013-08-21 株式会社 東北テクノアーチ リチウム電池
US10739337B2 (en) 2011-08-30 2020-08-11 Board Of Trustees Of Michigan State University Extraction and detection of pathogens using carbohydrate-functionalized biosensors
JP2013053208A (ja) * 2011-09-02 2013-03-21 Dic Corp 活性エネルギー線硬化型インクジェット記録用インク組成物及び画像形成方法
FR2979630B1 (fr) * 2011-09-05 2013-10-04 Univ Provence Aix Marseille 1 Copolymeres a blocs dont un polyanionique base sur un monomere anion de type tfsili comme electrolyte de batterie.
US9660294B2 (en) 2011-09-13 2017-05-23 Wildcat Discovery Technologies, Inc. Electrolyte materials for batteries and methods for use
WO2013039173A1 (ja) * 2011-09-16 2013-03-21 独立行政法人産業技術総合研究所 非水系水素イオン導電性電解質層を介設した反射型調光エレクトロクロミック素子及びそれを用いた調光部材
CN103814471A (zh) * 2011-09-19 2014-05-21 株式会社Lg化学 线缆型二次电池
CN103947027B (zh) 2011-10-13 2016-12-21 赛昂能源有限公司 电极结构及其制造方法
DE102011055028A1 (de) * 2011-11-04 2013-05-08 Jacobs University Bremen Ggmbh Elektrolyt-Zusatz für Lithium-basierte Energiespeicher
JP5871209B2 (ja) * 2011-11-15 2016-03-01 国立大学法人山形大学 ビススルホンイミド構造を持つポリマー及びこれを含む電極ならびに電池
WO2013072470A1 (en) * 2011-11-17 2013-05-23 Jonsson Erlendur Anions and derived salts with high dissociation in non-protogenic solvents
JP2013114934A (ja) * 2011-11-29 2013-06-10 Nippon Synthetic Chem Ind Co Ltd:The 金属塩、電極保護膜形成剤、それを用いた二次電池用電解質、及び二次電池
CN104080780B (zh) * 2011-11-30 2018-04-13 索尔维公司 氟化的麦德鲁姆酸的衍生物、其制备方法、及其作为溶剂添加剂的用途
CA2859023C (en) 2011-12-12 2023-08-22 View, Inc. Thin-film devices and fabrication
TWI447993B (zh) * 2011-12-30 2014-08-01 Ind Tech Res Inst 負極材料與負極極板
DE102012201942B8 (de) * 2012-02-09 2015-02-26 Ewe-Forschungszentrum Für Energietechnologie E. V. Verwendung eines aktivierten kohlenstoffhaltigen Materials, Verfahren zur Herstellung einer kohlenstoffhaltigen Elektrode, kohlestoffhaltige Elektrode, deren Verwendung sowie Vanadium-Redox-Flow-Zelle
US9077041B2 (en) 2012-02-14 2015-07-07 Sion Power Corporation Electrode structure for electrochemical cell
DE102012102162A1 (de) * 2012-03-14 2013-09-19 Westfälische Wilhelms-Universität Münster Körperschaft des öffentlichen Rechts Ionenleitende polymere Verbindung für elektrochemische Zellen
WO2013148242A1 (en) * 2012-03-28 2013-10-03 Cabot Corporation Oxidized carbon blacks treated with polyetheramines and coating compositions comprising same
WO2013142994A1 (en) * 2012-03-30 2013-10-03 Valorisation-Recherche, Limited Partnership Redox-active ionic liquids
CA2776178A1 (en) 2012-04-05 2013-10-05 Hydro-Quebec Ionic compounds
JP5660112B2 (ja) * 2012-04-27 2015-01-28 株式会社豊田自動織機 リチウムイオン二次電池用正極及びリチウムイオン二次電池
US9181173B2 (en) 2012-11-16 2015-11-10 Trinapco, Inc. Synthesis of tetrabutylammonium bis(fluorosulfonyl)imide and related salts
US9577289B2 (en) 2012-12-17 2017-02-21 Sion Power Corporation Lithium-ion electrochemical cell, components thereof, and methods of making and using same
JP6268833B2 (ja) * 2012-12-17 2018-01-31 株式会社豊田中央研究所 非水電解液二次電池及び非水電解液二次電池の製造方法
KR101991149B1 (ko) 2012-12-19 2019-06-19 시온 파워 코퍼레이션 전극 구조물 및 그의 제조 방법
JP6449169B2 (ja) 2012-12-20 2019-01-09 ソルヴェイ（ソシエテ アノニム） 電解質中の成分としての窒素含有複素環式アニオンの塩
CN102993196B (zh) * 2012-12-20 2015-01-28 北京科技大学 三唑类衍生物、其制备方法及其纳米粒子和纳米粒子的应用
US12261284B2 (en) 2013-03-15 2025-03-25 Sion Power Corporation Protective structures for electrodes
JP6201363B2 (ja) * 2013-03-25 2017-09-27 三菱ケミカル株式会社 非水系電解液及びそれを用いた非水系電解液電池
WO2015029248A1 (ja) * 2013-09-02 2015-03-05 株式会社日立製作所 負極活物質被覆材並びにこれを用いた負極材料、負極、リチウムイオン二次電池及び電池システム並びにモノマー及びその合成方法
JP6162084B2 (ja) * 2013-09-06 2017-07-12 富士フイルム株式会社 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、画像表示装置、ポリマー、キサンテン色素
US10385251B2 (en) 2013-09-30 2019-08-20 University Of Notre Dame Du Lac Compounds, complexes, compositions, methods and systems for heating and cooling
FR3011683A1 (fr) * 2013-10-03 2015-04-10 Arkema France Sel d'anion pentacyclique : composition pour batteries
FR3012462B1 (fr) * 2013-10-31 2016-01-01 Arkema France Compositions stables de poly (3,4-ethylenedioxythiophene) et de stabilisants anioniques a acidite limitee
US10086331B2 (en) 2013-11-05 2018-10-02 University Of Notre Dame Du Lac Carbon dioxide capture using phase change ionic liquids
KR102622781B1 (ko) 2014-05-01 2024-01-08 시온 파워 코퍼레이션 전극 제조 방법 및 관련 제품
CA2948001C (en) 2014-05-12 2023-03-14 Johna Leddy Lanthanide electrochemistry
US10601031B2 (en) 2014-06-06 2020-03-24 Robert Bosch Gmbh Polymer electrolyte for a lithium sulfur cell
JP6541508B2 (ja) * 2014-08-25 2019-07-10 住友化学株式会社 塩、樹脂、レジスト組成物及びレジストパターンの製造方法
CN104600357B (zh) * 2014-12-08 2017-05-31 上海大学 聚合物复合材料固态电解质及其制备方法
US10068715B2 (en) 2014-12-12 2018-09-04 Corning Incorporated Activated carbon and electric double layer capacitor thereof
US10826113B2 (en) * 2015-04-13 2020-11-03 Global Graphene Group, Inc. Zinc ion-exchanging energy storage device
JP6658204B2 (ja) * 2015-04-28 2020-03-04 信越化学工業株式会社 光酸発生剤、レジスト組成物及びパターン形成方法
DE102015210388A1 (de) * 2015-06-05 2016-12-08 Siemens Aktiengesellschaft Organische Heterozyklische Alkalimetallsalze als n-Dotierstoffe in der Organischen Elektronik
EP3113275B1 (de) * 2015-06-29 2021-06-09 VARTA Micro Innovation GmbH Sekundäre magnesiumbatterie und elektrolytsystem sowie elektrode für eine sekundäre magnesiumbatterie
WO2017011759A1 (en) * 2015-07-15 2017-01-19 Trustees Of Boston University Ionic liquid electrolytes and electrochemical devices comprising same
JP2017066377A (ja) * 2015-09-29 2017-04-06 Jsr株式会社 着色組成物、着色硬化膜、並びに表示素子及び固体撮像素子
GB2544495B (en) 2015-11-17 2018-12-05 Nexeon Ltd Surface modified electrochemically active material
JP2019503032A (ja) * 2015-11-17 2019-01-31 ネグゼオン・リミテッドＮｅｘｅｏｎ Ｌｔｄ 官能化された電気化学的活性材料および官能化の方法
KR102056591B1 (ko) * 2015-12-07 2019-12-17 주식회사 엘지화학 점착제 조성물
TWI662364B (zh) 2015-12-31 2019-06-11 Rohm And Haas Electronic Materials Llc 光致抗蝕劑組合物、包含光致抗蝕劑組合物的經塗佈基板及形成電子裝置的方法
TWI656111B (zh) 2015-12-31 2019-04-11 Rohm And Haas Electronic Materials Llc 光酸產生劑
JP6946294B2 (ja) * 2016-07-26 2021-10-06 東ソー・ファインケム株式会社 ハロゲン化物が低減された重合性官能基を有するスルホンイミドの有機溶剤溶液
JP6853636B2 (ja) * 2016-09-08 2021-03-31 三菱マテリアル電子化成株式会社 ペルフルオロアルキルスルホンアミドの製造方法
JP6744848B2 (ja) * 2016-09-13 2020-08-19 信越化学工業株式会社 粘着剤組成物、生体電極、及び生体電極の製造方法
JP6761386B2 (ja) * 2016-09-29 2020-09-23 信越化学工業株式会社 粘着剤組成物、生体電極、生体電極の製造方法、及び塩
JP6761384B2 (ja) * 2016-09-29 2020-09-23 信越化学工業株式会社 粘着剤組成物、生体電極、及び生体電極の製造方法
KR102141267B1 (ko) * 2016-11-04 2020-08-04 주식회사 엘지화학 방향족 고리를 포함하는 화합물 및 이를 포함하는 중합체
JP6919993B2 (ja) 2017-01-06 2021-08-18 信越化学工業株式会社 生体電極組成物、生体電極及び生体電極の製造方法
JP6966310B2 (ja) * 2017-02-06 2021-11-10 信越化学工業株式会社 生体電極組成物、生体電極、生体電極の製造方法、及び高分子化合物
JP6892376B2 (ja) 2017-02-14 2021-06-23 信越化学工業株式会社 生体電極組成物、生体電極、生体電極の製造方法、及び高分子化合物
JP6765988B2 (ja) * 2017-02-22 2020-10-07 信越化学工業株式会社 導電性ポリマー用高分子化合物及びその製造方法
JP6661212B2 (ja) * 2017-02-22 2020-03-11 信越化学工業株式会社 導電性ポリマー複合体及び基板
ES2693587A1 (es) * 2017-06-09 2018-12-12 Universidad Carlos Iii De Madrid Sales a base de aniones orgánicos de sulfonamidas y sus usos
US11719606B2 (en) * 2017-07-06 2023-08-08 University Public Corporation Osaka Method and reagent for clearing biological tissue
KR102719408B1 (ko) * 2017-08-08 2024-10-17 젠텍스 코포레이션 투명한 이온 교환 멤브레인을 갖는 전기 광학 장치
US10232360B1 (en) 2017-09-12 2019-03-19 Chevron Phillips Chemical Company, Lp Use of organic dopants to enhance acetylene hydrogenation catalysts
US10245583B1 (en) * 2017-09-12 2019-04-02 Chevron Phillips Chemical Company, Lp Use of charge-containing molecules linked with covalent bonds to enhance acetylene hydrogenation catalysts
JP6845191B2 (ja) * 2017-10-19 2021-03-17 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
JP6920000B2 (ja) 2017-10-26 2021-08-18 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
KR102228070B1 (ko) * 2017-11-01 2021-03-12 주식회사 엘지화학 화학 증폭형 포토레지스트 조성물 및 이를 이용한 포토레지스트 필름
JP6850279B2 (ja) * 2017-11-21 2021-03-31 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
CN107706463B (zh) * 2017-11-23 2018-11-06 林宝领 一种锂电池的亚硝基接枝碳酸酯电解液及制备方法
CN109851703B (zh) * 2017-11-30 2020-10-23 比亚迪股份有限公司 适用于粘结剂的偏二氟乙烯类共聚物及其制备方法和应用
CN109860471B (zh) * 2017-11-30 2020-12-25 比亚迪股份有限公司 聚合物隔膜及其制备方法和应用及锂电池
CN109851704B (zh) * 2017-11-30 2020-06-19 比亚迪股份有限公司 聚合物隔膜及其制备方法和应用及锂电池
CN109935902B (zh) * 2017-12-19 2021-10-19 成都大超科技有限公司 固态电解质及其锂电池电芯、锂电池
JP6839125B2 (ja) 2018-04-02 2021-03-03 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
JP7080732B2 (ja) * 2018-06-01 2022-06-06 三菱マテリアル電子化成株式会社 含フッ素スルホニルイミド塩基含有シリコーン化合物とそれを含有する導電性シリコーン組成物
US11394056B2 (en) * 2018-06-08 2022-07-19 Solid State Battery Incorporated Composite solid polymer electrolytes for energy storage devices
JP7111653B2 (ja) 2018-06-25 2022-08-02 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
JP7099990B2 (ja) * 2018-06-26 2022-07-12 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
JP7222396B2 (ja) 2018-07-20 2023-02-15 株式会社ニコン カメラアクセサリおよび情報送信方法
WO2020025499A1 (en) 2018-07-31 2020-02-06 Solvay Sa New components for electrolyte compositions
WO2020025501A1 (en) 2018-07-31 2020-02-06 Solvay Sa New components for electrolyte compositions
EP3604276A1 (en) 2018-07-31 2020-02-05 Solvay Sa New components for electrolyte compositions
EP3605698A1 (en) 2018-07-31 2020-02-05 Solvay Sa New components for electrolyte compositions
EP3605700A1 (en) 2018-07-31 2020-02-05 Solvay Sa New components for electrolyte compositions
EP3605699A1 (en) 2018-07-31 2020-02-05 Solvay Sa New components for electrolyte compositions
WO2020025502A1 (en) 2018-07-31 2020-02-06 Solvay Sa New components for electrolyte compositions
JP6966396B2 (ja) * 2018-08-23 2021-11-17 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
KR102650658B1 (ko) * 2018-11-15 2024-03-25 삼성전자주식회사 헤테로고리 방향족 구조의 음이온을 포함하는 금속염 및 그 제조방법, 그리고 상기 금속염을 포함하는 전해질 및 전기화학소자
CN109776709B (zh) * 2018-12-25 2021-09-07 广东工业大学 一种聚对苯乙烯磺酰(三氟甲基磺酰)亚胺锂-聚碳酸亚乙烯基酯共聚物及其应用
PL3883037T3 (pl) * 2019-01-17 2023-05-08 Lg Energy Solution, Ltd. Elektrolit dla akumulatora litowego i zawierający go akumulator litowy
JP7237606B2 (ja) * 2019-01-25 2023-03-13 国立大学法人東京農工大学 ４－スチレン誘導体を重合したポリマー並びに、これを用いたマグネシウム二次電池用バインダーもしくはコート剤、及びマグネシウム二次電池
EP3705035A1 (en) * 2019-03-07 2020-09-09 Nederlandse Organisatie voor toegepast- natuurwetenschappelijk Onderzoek TNO Manufacturing of skin-compatible electrodes
DE102019208914A1 (de) * 2019-06-19 2020-12-24 Robert Bosch Gmbh Salz mit Anion mit unfluorierter Dialkylamid-Sulfonyl- und/oder -Sulfoximid-Gruppe und mit Perfluoralkyl-Sulfonyl-Gruppe
CN110305172B (zh) * 2019-06-26 2020-09-01 武汉大学 一种钴膦酸盐及其制备方法和作为宽温域质子传导材料的应用
CN110368899A (zh) * 2019-07-16 2019-10-25 邱越 一种活性炭复合材料及其制备方法和应用
CN110721745B (zh) * 2019-09-25 2020-09-08 中山大学 一种抗中毒的水溶性过氧化物分解催化剂及其制备方法和应用
KR102735774B1 (ko) * 2019-12-05 2024-11-29 주식회사 엘지에너지솔루션 리튬 이차전지용 비수전해액 및 이를 포함하는 리튬 이차전지
WO2021150022A1 (ko) * 2020-01-21 2021-07-29 하이드로메이트 코팅스, 인크. 비닐 아미노 비방향족고리 화합물로 표면개질된 기질 및 그의 표면개질 방법
US12077646B2 (en) 2020-01-21 2024-09-03 Quantum MicroMaterials, Inc. Coating substrate by polymerization of amine compound and apparatus having polymer coated substrate
CN115004096B (zh) * 2020-02-05 2024-09-13 金泰克斯公司 电致变色化合物
CN111477962B (zh) * 2020-05-29 2021-07-20 珠海市赛纬电子材料股份有限公司 一种锂离子电池非水电解液及含该非水电解液的锂离子电池
CN111883836A (zh) * 2020-07-24 2020-11-03 香河昆仑化学制品有限公司 一种锂离子电池非水电解液和锂离子电池
CN111883834B (zh) * 2020-07-24 2022-12-13 香河昆仑新能源材料股份有限公司 一种非水锂离子电池电解液添加剂、包含其的电解液以及锂离子电池
CN111934015B (zh) * 2020-08-28 2022-08-19 珠海市赛纬电子材料股份有限公司 一种锂离子电池非水电解液及含该非水电解液的锂离子电池
CN116783734A (zh) * 2020-12-29 2023-09-19 川崎摩托株式会社 质子传导型二次电池用正极活性物质材料及具备该正极活性物质材料的质子传导型二次电池
WO2022238312A1 (en) 2021-05-12 2022-11-17 Litronik Batterietechnologie Gmbh Primary alkali metal cells with geminal dinitrile additives
CN117337506A (zh) * 2021-05-17 2024-01-02 中央硝子株式会社 非水系电解液和使用其的非水系电解液二次电池
KR102913782B1 (ko) * 2021-11-16 2026-01-15 주식회사 엘지에너지솔루션 신규한 비수계 전해액용 첨가제 및 이를 포함하는 리튬 이차전지
CN115286587B (zh) * 2022-07-06 2024-02-23 珠海中科先进技术研究院有限公司 一种高离域的碱金属化合物及其制备方法和应用
WO2024115088A1 (en) 2022-11-29 2024-06-06 Litronik Batterietechnologie Gmbh Primary alkali metal cells with cyano-cycloalkanes additives
WO2025019663A2 (en) * 2023-07-18 2025-01-23 Massachusetts Institute Of Technology Fluorinated sulfonamide-based electrolytes for non-lithium batteries thereof
WO2025057818A1 (ja) * 2023-09-12 2025-03-20 住友化学株式会社 電解質組成物及び電池
CN121866666A (zh) * 2023-09-12 2026-04-14 住友化学株式会社 电解质组合物及电池
WO2025094896A1 (ja) * 2023-10-31 2025-05-08 住友化学株式会社 電池
FR3155529A1 (fr) 2023-11-16 2025-05-23 Commissariat A L'energie Atomique Et Aux Energies Alternatives Procédé de synthèse de sels comportant un anion organique utiles comme matériaux conducteurs ioniques
WO2025197682A1 (ja) * 2024-03-18 2025-09-25 住友化学株式会社 電池
WO2026017310A1 (en) 2024-07-16 2026-01-22 Litronik Batterietechnologie Gmbh Primary alkali metal cells with cyano-cycloalkenes additives
EP4715902A1 (en) * 2024-09-23 2026-03-25 Belenos Clean Power Holding AG Ionically conductive polymeric binder for cathode
EP4715926A1 (en) * 2024-09-23 2026-03-25 Belenos Clean Power Holding AG Ionically conductive polymers for gel polymer electrolyte, and gel polymer electrolyte comprising such an ionically conductive polymer

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1306564A (en) * 1970-04-13 1973-02-14 Minnesota Mining & Mfg Fluoroalkylsulphonamidoaryl compounds
EP0096629A1 (fr) * 1982-06-01 1983-12-21 ANVAR Agence Nationale de Valorisation de la Recherche Bis perhalogénoacyl - ou sulfonyl - imidures de métaux alcalins, leurs solutions solides avec des matières plastiques et leur application à la constitution d'éléments conducteurs pour des générateurs électrochimiques
WO1988003331A1 (fr) * 1986-10-30 1988-05-05 Centre National De La Recherche Scientifique (Cnrs Nouveau materiau a conduction ionique constitue par un sel en solution dans un electrolyte liquide
WO1992016028A1 (fr) * 1991-03-07 1992-09-17 Centre National De La Recherche Scientifique (Cnrs) Materiaux polymeriques a conduction ionique
WO1993016988A1 (fr) * 1992-02-21 1993-09-02 Centre National De La Recherche Scientifique Monomeres derives de sultones perhalogenees et polymeres obtenus a partir de ces monomeres
WO1995026056A1 (fr) * 1994-03-21 1995-09-28 Centre National De La Recherche Scientifique Materiau a conduction ionique presentant de bonnes proprietes anti-corrosion
EP0731518A1 (en) * 1995-03-06 1996-09-11 Minnesota Mining And Manufacturing Company Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them
EP0779671A2 (fr) * 1995-12-14 1997-06-18 Electricite De France Bis (phénylsulfonyl) imidures, leur procédé de préparation et matériaux à conduction ionique les comprenant

Family Cites Families (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3054800A (en) * 1949-09-17 1962-09-18 Harry P Burchfield 3, 5-dinitro-1, 2, 4-triazoles and process for preparing same
US2959475A (en) * 1957-02-19 1960-11-08 Du Pont Method for the control of weeds
CH484920A (de) * 1966-05-13 1970-03-13 Sandoz Ag Verfahren zur Herstellung von Aminsalzen von 1,2,4-Triazolen
FR2097745A5 (en) * 1970-04-13 1972-03-03 Minnesota Mining & Mfg Fluoroalkyl sulphonamido-diaryl-(thio)-ethers and derivs - herbicides antiinflamma
BE791595A (fr) 1971-11-18 1973-05-17 Omf California Inc Electrolyte pour accumulateur
JPS5148516B2 (enExample) * 1973-02-07 1976-12-21
DD118433A1 (enExample) * 1975-03-17 1976-03-05
US4226873A (en) 1977-02-23 1980-10-07 Gulf Oil Corporation 5-Substituted-3-fluorosulfonyl-4H-1,2,4-triazoles and use as insecticides and miticides
JPS53117094A (en) * 1977-03-23 1978-10-13 Mitsubishi Gas Chem Co Inc Preparation of composition and high polymer
US4105525A (en) * 1978-01-23 1978-08-08 Orion Research Incorporated Internal standard electrolyte for ammonia sensor
EP0010396A1 (en) * 1978-10-24 1980-04-30 Fbc Limited Fungicidal and herbicidal compositions, certain cyanomethane and cyanoethene derivatives being active agents thereof, the preparation of these derivatives and methods for combating fungi and weeds
DE3230923A1 (de) * 1982-08-20 1984-02-23 Basf Ag, 6700 Ludwigshafen Thiadiazinone, verfahren zu ihrer herstellung und diese enthaltende fungizide
JPS6020950A (ja) * 1983-07-13 1985-02-02 Nippon Zeon Co Ltd 硬質用塩化ビニル樹脂組成物
US5232940A (en) * 1985-12-20 1993-08-03 Hatton Leslie R Derivatives of N-phenylpyrazoles
US4664761A (en) * 1985-12-27 1987-05-12 Uop Inc. Electrochemical method and apparatus using proton-conducting polymers
US4664757A (en) * 1985-12-27 1987-05-12 Uop Inc. Method and apparatus for gas detection using proton-conducting polymers
JPH0654686B2 (ja) * 1986-01-14 1994-07-20 三洋電機株式会社 二次電池
JPS62219908A (ja) * 1986-03-20 1987-09-28 日本ケミコン株式会社 電解コンデンサ用電解液
US4714569A (en) * 1986-07-22 1987-12-22 Toska Co., Ltd. Process for preparing conductive coating composition
FR2606216A1 (fr) 1986-10-30 1988-05-06 Elf Aquitaine Materiau a conduction ionique
DE3781144T2 (de) * 1986-11-10 1993-04-08 Nippon Catalytic Chem Ind Gefaerbte sphaerische feinpartikel, verfahren zu ihrer herstellung und ihre anwendung.
US4966954A (en) * 1987-03-04 1990-10-30 Rensselaer Polytechnic Institute Production and processing of thermally stable polyenaminonitriles and polyaminoquinolines therefrom
US4882244A (en) * 1987-04-02 1989-11-21 The University Of Michigan-Ann Arbor Battery containing a metal anode and an electrolyte providing high rates of metal electrolysis at near ambient temperatures
US4835074A (en) * 1987-09-25 1989-05-30 The Electrosynthesis Company, Inc. Modified carbons and electrochemical cells containing the same
JPH01152165A (ja) * 1987-12-09 1989-06-14 Nippon Shokubai Kagaku Kogyo Co Ltd 表面処理されたカーボンブラツクの製造方法
JP2724377B2 (ja) * 1988-05-12 1998-03-09 汪芳 白井 イオン伝導性組成物
FR2645533B1 (fr) 1989-04-06 1991-07-12 Centre Nat Rech Scient Procede de synthese de sulfonylimidures
NL9001075A (enExample) * 1990-05-04 1991-12-02 Duphar Int Res
IT1246357B (it) * 1990-07-12 1994-11-17 Ausimont Spa Processo per la preparazione di composti perfluoroalcossisolfonici
US5273840A (en) * 1990-08-01 1993-12-28 Covalent Associates Incorporated Methide salts, formulations, electrolytes and batteries formed therefrom
US5281261A (en) * 1990-08-31 1994-01-25 Xerox Corporation Ink compositions containing modified pigment particles
EP0532408A1 (fr) * 1991-09-13 1993-03-17 Saint-Gobain Vitrage International Polymère conducteur protonique, application en tant qu'électrolyte dans des dispositifs électrochimiques
FR2683524A1 (fr) * 1991-11-08 1993-05-14 Centre Nat Rech Scient Derives des bis(perfluorosulfonyl)methanes, leur procede de preparation, et leurs utilisations .
JP2845389B2 (ja) * 1992-03-10 1999-01-13 大日精化工業株式会社 熱転写記録用着色組成物
DE4217366A1 (de) 1992-05-26 1993-12-02 Bayer Ag Imide und deren Salze sowie deren Verwendung
US5354784A (en) * 1992-08-10 1994-10-11 Arakawa Kagaku Kogyo Kabushiki Kaisha Cyclopentadienyliron complex salt, process for preparing the same and photopolymerizable composition containing the same
US5518841A (en) * 1993-02-12 1996-05-21 Matsushita Electric Industrial Co., Ltd. Composite cathode
US5538812A (en) * 1994-02-04 1996-07-23 Moltech Corporation Electrolyte materials containing highly dissociated metal ion salts
JP3499916B2 (ja) 1994-05-30 2004-02-23 三洋電機株式会社 高分子固体電解質電池とその製造方法
FR2723098B1 (fr) * 1994-07-28 1996-10-04 Centre Nat Rech Scient Materiau macromoleculaire comportant des substituants ioniques et son utilisation dans les systemes electrochimiques
JP3117369B2 (ja) * 1994-09-12 2000-12-11 セントラル硝子株式会社 スルホンイミドの製造方法
US5525436A (en) * 1994-11-01 1996-06-11 Case Western Reserve University Proton conducting polymers used as membranes
US5609990A (en) 1995-02-08 1997-03-11 Imation Corp. Optical recording disk having a sealcoat layer
WO1996024929A1 (en) 1995-02-08 1996-08-15 Minnesota Mining And Manufacturing Company Reduced solvent antistatic hard coat
US5874616A (en) 1995-03-06 1999-02-23 Minnesota Mining And Manufacturing Company Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides
US5748439A (en) * 1995-06-06 1998-05-05 Telectronics Pacing Systems, Inc. Capacitors having high strength electrolytic capacitor separators
JPH0912920A (ja) * 1995-06-28 1997-01-14 Nippon Oil Co Ltd 炭素材料の製造方法
US5831108A (en) * 1995-08-03 1998-11-03 California Institute Of Technology High metathesis activity ruthenium and osmium metal carbene complexes
US5691081A (en) 1995-09-21 1997-11-25 Minnesota Mining And Manufacturing Company Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts
US5795496A (en) * 1995-11-22 1998-08-18 California Institute Of Technology Polymer material for electrolytic membranes in fuel cells
DE69618019T2 (de) 1996-03-26 2002-08-01 Minnesota Mining And Mfg. Co., Saint Paul Kationisch polymerisierbare zusmmensetzungen, die zur beschichtung in einem elektrostatischen verfahren verwendet werden können
US5962546A (en) 1996-03-26 1999-10-05 3M Innovative Properties Company Cationically polymerizable compositions capable of being coated by electrostatic assistance
US5817376A (en) 1996-03-26 1998-10-06 Minnesota Mining And Manufacturing Company Free-radically polymerizable compositions capable of being coated by electrostatic assistance
US5688613A (en) * 1996-04-08 1997-11-18 Motorola, Inc. Electrochemical cell having a polymer electrolyte
DE19632285A1 (de) * 1996-08-09 1998-02-19 Hoechst Ag Protonenleiter mit einer Temperaturbeständigkeit in einem weiten Bereich und guten Protonenleitfähigkeiten
JP4823401B2 (ja) * 1996-12-30 2011-11-24 イドロ―ケベック 過フッ化アミド塩及びイオン伝導物質としてのその使用方法
US6063522A (en) 1998-03-24 2000-05-16 3M Innovative Properties Company Electrolytes containing mixed fluorochemical/hydrocarbon imide and methide salts
US5874606A (en) 1998-03-31 1999-02-23 Occidental Chemical Corporation Process for making o-arylbenzonitriles
US6350545B2 (en) 1998-08-25 2002-02-26 3M Innovative Properties Company Sulfonylimide compounds
US6294289B1 (en) 1998-08-25 2001-09-25 3M Innovative Properties Company Cyano-substituted methide and amide salts

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1306564A (en) * 1970-04-13 1973-02-14 Minnesota Mining & Mfg Fluoroalkylsulphonamidoaryl compounds
EP0096629A1 (fr) * 1982-06-01 1983-12-21 ANVAR Agence Nationale de Valorisation de la Recherche Bis perhalogénoacyl - ou sulfonyl - imidures de métaux alcalins, leurs solutions solides avec des matières plastiques et leur application à la constitution d'éléments conducteurs pour des générateurs électrochimiques
WO1988003331A1 (fr) * 1986-10-30 1988-05-05 Centre National De La Recherche Scientifique (Cnrs Nouveau materiau a conduction ionique constitue par un sel en solution dans un electrolyte liquide
WO1992016028A1 (fr) * 1991-03-07 1992-09-17 Centre National De La Recherche Scientifique (Cnrs) Materiaux polymeriques a conduction ionique
WO1993016988A1 (fr) * 1992-02-21 1993-09-02 Centre National De La Recherche Scientifique Monomeres derives de sultones perhalogenees et polymeres obtenus a partir de ces monomeres
WO1995026056A1 (fr) * 1994-03-21 1995-09-28 Centre National De La Recherche Scientifique Materiau a conduction ionique presentant de bonnes proprietes anti-corrosion
EP0731518A1 (en) * 1995-03-06 1996-09-11 Minnesota Mining And Manufacturing Company Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them
EP0779671A2 (fr) * 1995-12-14 1997-06-18 Electricite De France Bis (phénylsulfonyl) imidures, leur procédé de préparation et matériaux à conduction ionique les comprenant

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
D.D. DESMARTEAU ET AL: "N-Fluoro-bis(trifluoromethanesulfonyl)imide. An improved synthesis", JOURNAL OF FLUORINE CHEMISTRY, vol. 52, no. 1, 1 April 1991 (1991-04-01), LAUSANNE, CH, pages 7 - 12, XP002025807 *
D.D. DESMARTEAU: "Novel perfluorinated ionomers and ionenes", JOURNAL OF FLUORINE CHEMISTRY, vol. 72, no. 2, June 1995 (1995-06-01), LAUSANNE, CH, pages 203 - 208, XP002025806 *
H.W. ROESKY ET AL: "Darstellung von N-Trifluormethansulfonyl-sulfonyl fluoridamid und einige Reaktionen", INORGANIC AND NUCLEAR CHEMISTRY LETTERS, vol. 7, no. 2, 1971, pages 171 - 175, XP000618718 *
R. LIS ET AL.: "Synthesis and antiarrhythmic activity of novel 3-alkyl-1-[omega-[4-[(alkylsulfonyl)amino]phenyl]-omega-hydroxyalkyl]-1H-imidazolium salts and related compounds", JOURNAL OF MEDICINAL CHEMISTRY, vol. 30, no. 4, April 1987 (1987-04-01), WASHINGTON, DC, US, pages 696 - 704, XP002062045 *
R.E. BANKS ET AL.: "N-Halogeno compounds. Part 11. Perfluoro-[N-fluoro-N- (4-pyridyl)-methanesulphonamide], a powerful new electrophilic fluorinating agent", JOURNAL OF FLUORINE CHEMISTRY, vol. 46, no. 2, February 1990 (1990-02-01), LAUSANNE, CH, pages 297 - 305, XP002062043 *
V.A. PETROV ET AL.: "Synthesis of polyfluoro-2-alkanesulfonyl-3,3- dialkoxyaziridines", JOURNAL OF FLUORINE CHEMISTRY, vol. 68, no. 3, September 1994 (1994-09-01), LAUSANNE, CH, pages 277 - 86, XP002062044 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002508576A (ja) * 1998-03-24 2002-03-19 ミネソタ マイニング アンド マニュファクチャリング カンパニー 混合フルオロカーボン／炭化水素イミド塩およびメチド塩を含有する電解質
JP2003532619A (ja) * 1998-08-25 2003-11-05 ミネソタ マイニング アンド マニュファクチャリング カンパニー スルホニルイミドおよび導電性塩としてのその使用
WO2002072519A3 (en) * 2001-03-12 2002-11-21 Univ Belfast Process catalysed by fluoroalkylsulfonated compounds, preferably bis-triflimide compounds
WO2002072260A3 (en) * 2001-03-12 2004-02-26 Univ Belfast Metal bis-triflimide compounds, their synthesis and their uses
US6998497B2 (en) 2001-03-12 2006-02-14 The Queen's University Of Belfast Metal bis-triflimide compounds and methods for synthesis of metal bis-triflimide compounds
AU2002241085B2 (en) * 2001-03-12 2007-03-29 The Queen's University Of Belfast Processes using metal bis-triflimide compounds
US7781625B2 (en) 2001-03-12 2010-08-24 The Queen's University Of Belfast Process catalysed by bis-trifilmide compounds
EP4480946A1 (en) * 2017-03-27 2024-12-25 Hydro-Québec Salts for use in electrolyte compositions or as electrode additives

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