CA2266643A1 - Ionic compounds with delocalized anionic charge, their use as components of ionic conductors or catalyst - Google Patents
Ionic compounds with delocalized anionic charge, their use as components of ionic conductors or catalystInfo
- Publication number
- CA2266643A1 CA2266643A1 CA002266643A CA2266643A CA2266643A1 CA 2266643 A1 CA2266643 A1 CA 2266643A1 CA 002266643 A CA002266643 A CA 002266643A CA 2266643 A CA2266643 A CA 2266643A CA 2266643 A1 CA2266643 A1 CA 2266643A1
- Authority
- CA
- Canada
- Prior art keywords
- compound according
- ionic compound
- ionic
- cation
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000008040 ionic compounds Chemical class 0.000 title claims abstract 31
- 239000003054 catalyst Substances 0.000 title claims abstract 3
- 125000000129 anionic group Chemical group 0.000 title 1
- 239000010416 ion conductor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 150000001768 cations Chemical class 0.000 claims abstract 11
- 229920000642 polymer Polymers 0.000 claims abstract 6
- 238000002360 preparation method Methods 0.000 claims abstract 6
- 239000004020 conductor Substances 0.000 claims abstract 5
- -1 ammonium ions Chemical class 0.000 claims 26
- 239000003792 electrolyte Substances 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229910052698 phosphorus Inorganic materials 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 239000011574 phosphorus Chemical group 0.000 claims 4
- 239000011701 zinc Substances 0.000 claims 4
- 150000001340 alkali metals Chemical class 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002500 ions Chemical class 0.000 claims 3
- 238000006116 polymerization reaction Methods 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 101100365877 Caenorhabditis elegans cdl-1 gene Proteins 0.000 claims 2
- 101001047513 Mus musculus Lethal(2) giant larvae protein homolog 1 Proteins 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 229910052793 cadmium Inorganic materials 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 125000002091 cationic group Chemical group 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229910052753 mercury Inorganic materials 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 238000005698 Diels-Alder reaction Methods 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical class C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 239000012964 benzotriazole Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 229920000547 conjugated polymer Polymers 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical group [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 claims 1
- 150000001457 metallic cations Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-O n,n-dimethylpyridin-1-ium-4-amine Chemical compound CN(C)C1=CC=[NH+]C=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-O 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 238000005121 nitriding Methods 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- 125000002743 phosphorus functional group Chemical group 0.000 claims 1
- 229920006112 polar polymer Polymers 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000002577 pseudohalo group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 239000002001 electrolyte material Substances 0.000 abstract 1
Classifications
-
- Y02E60/12—
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Abstract
L'invention concerne un composé ionique répondant à la formule ¢R1X1(Z1)-Q--X2(Z2)-R2!m Mm+ dans laquelle Mm+ est un cation de valence m, chacun des Xi est S=Z3, S=Z4, P-R3 ou P-R4; -Q est N, CR5, CCN ou CSO2R5, chacun des Zi est =O, =NCN, =C(CN)2, =NS(=Z)2R6 ou =C¢S(=Z)2R6!2, chacun des Ri, est Y, YO-, YS, Y2N- ou F, Y représente un radical organique monovalent ou bien Y est une unité de répétition d'une trame polymérique. Les composés sont utiles pour l'élaboration de matériaux à conduction ionique ou d'électrolyte, comme catalyseurs et pour le dopage de polymères.The invention relates to an ionic compound corresponding to the formula ¢ R1X1 (Z1) -Q - X2 (Z2) -R2! M Mm + in which Mm + is a cation of valence m, each of the Xi is S = Z3, S = Z4 , P-R3 or P-R4; -Q is N, CR5, CCN or CSO2R5, each of Zi is = O, = NCN, = C (CN) 2, = NS (= Z) 2R6 or = C ¢ S (= Z) 2R6! 2, each of Ri, is Y, YO-, YS, Y2N- or F, Y represents a monovalent organic radical or else Y is a repeating unit of a polymeric frame. The compounds are useful for the preparation of ionically conductive or electrolyte materials, as catalysts and for doping polymers.
Claims (40)
- Mm est le proton, ou un cation métallique ayant la valence m choisi parmi les ions des métaux alcalins, des métaux alcalino-terreux, des métaux de transition, des terres rares, ou un cation organique onium, ou un cation organo-métallique, 1 < m < 3 ;
- X1 et X2, désignés ci-après par Xi, représentent indépendamment l'un de l'autre S=Z3, S=Z4, P-R3 ou P-R4 ;
- Q représente N, CR5, CCN ou CSO2R5 ;
_ Z1, Z2, Z3 et Z4, désignés ci-après par zi, représentent indépendamment les uns des autres =O, =NC~N, =C(C~N)2, =NS(=Z)2R6 ou =C[S(=Z)2R6]2, Z ayant la même signification que zi, étant entendu que, dans un segment -X1-Q-X2-, au plus 3 groupes zi représentent =O ;
- R1, R2, R3, R4, R5 et R6, désignés ci-après par Ri, représentent indépendamment les uns des autres Y, YO-, YS-, Y2N- ou F ;
- Y représente un radical organique monovalent, ayant de préférence de 1 à 16 atomes de carbone, choisi parmi les radicaux alkyles, alkényles, oxa-alkyles, oxa-alkényles, aza-alkyles, aza-alkényles, aryles ou alkylaryles, perfluroalkyles, ou parmi les radicaux obtenus à partir des radicaux précités par substitution, dans les chaînes et / ou la partie aromatique, par des hétéroatomes tels que les halogènes, l'oxygène, l'azote, le soufre, le phosphore, étant entendu que le soufre ou le phosphore sont présents, ils peuvent éventuellement être lies à des atomes d'oxygène ou d'azote substitues, ou bien Y est une unité de répétition d'une trame polymérique. 1. Ionic compound corresponding to the formula in which :
- Mm is the proton, or a metal cation having the valence m chosen from among the ions of alkali metals, alkaline earth metals, transition metals, rare earths, or an organic onium cation, or a cation organo-metallic, 1 <m <3;
- X1 and X2, designated below by Xi, represent independently of each other S = Z3, S = Z4, P-R3 or P-R4;
- Q represents N, CR5, CCN or CSO2R5;
_ Z1, Z2, Z3 and Z4, designated below by zi, represent independently of each other = O, = NC ~ N, = C (C ~ N) 2, = NS (= Z) 2R6 or = C [S (= Z) 2R6] 2, Z having the same meaning that zi, it being understood that in a segment -X1-Q-X2-, at most 3 groups zi represent = O;
- R1, R2, R3, R4, R5 and R6, hereinafter referred to as Ri, independently represent Y, YO-, YS-, Y2N- or F;
- Y represents a monovalent organic radical, preferably having from 1 to 16 carbon atoms, chosen among the alkyl, alkenyl, oxa-alkyl radicals, oxa-alkenyls, aza-alkyls, aza-alkenyls, aryls or alkylaryls, perfluroalkyles, or among the radicals obtained from the aforementioned radicals by substitution, in the chains and / or the aromatic part, by heteroatoms such as halogens, oxygen, nitrogen, sulfur, phosphorus, it being understood that sulfur or phosphorus are present, they can possibly be linked to atoms substituted oxygen or nitrogen, or Y is a unit of repeating a polymer frame.
ou As et portés par des molécules organiques, les groupes trialkyl-silyle, tétraalkyl-germanyle et dialkyl-stannyle dans lesquels les radicaux alkyles ont de 1 à 10 atomes de carbone. 4. Ionic compound according to claim 1, characterized in that the cation Mm is an organometallic cation chosen from metallocenium ions, cations metals coordinated by atoms such as 0, S, Se N, P
or As and carried by organic molecules, the groups trialkyl-silyl, tetraalkyl-germanyl and dialkyl-stannyl in which the alkyl radicals have from 1 to 10 atoms of carbon.
- A est un métal alcalin, un proton, une base aminée ou phosphorée, un groupe trialkyl silyle, un groupe dialkyle stannyle, LiH, MgCl, Li, MgL1, ZnL1, CdL1, Cu, Mg, Zn, Cd, Hg, un groupement trialkyl-silyle, trialkyle-germanyle ou trialkyle-stannyle, - L et L1 sont des groupes partants 21. Process for the preparation of a compound according to the claim 1, characterized in that it consists in making reacting a compound R1-X1 (Z1) -Q-X2 (L) R2 on a compound A2Z2, wherein :
- A is an alkali metal, a proton, an amino base or phosphorus, a trialkyl silyl group, a dialkyl group stannyle, LiH, MgCl, Li, MgL1, ZnL1, CdL1, Cu, Mg, Zn, Cd, Hg, a trialkyl-silyl, trialkyl-germanyl group or trialkyl-stannyl, - L and L1 are leaving groups
- A est un métal alcalin, un proton, une base aminée ou phosphorée, un groupe trialkyl silyle, un groupe dialkyle stannyle, LiH, Li, MgL1, ZnL1, CdL1, Cu, Mg, Zn, Cd, Hg, un groupement trialkyl-silyle, trialkyle-germanyle ou trialkyle-stannyle, - L et L1 sont des groupes partants. 22. Process for the preparation of a compound according to the claim 1, characterized in that it consists in making react a compound R1-X1 (Z1) -QA2 on a compound L-X2 (Z2) R2 in which :
- A is an alkali metal, a proton, an amino base or phosphorus, a trialkyl silyl group, a dialkyl group stannyle, LiH, Li, MgL1, ZnL1, CdL1, Cu, Mg, Zn, Cd, Hg, un trialkyl-silyl, trialkyl-germanyl group or trialkyl-stannyl, - L and L1 are leaving groups.
métallique de la sulfonamide tel que R3SO2NLi2 ou R3SO2NNa2, et à effectuer un échange d'ions pour obtenir le cation souhaité. 26. Process for the preparation of a compound according to the claim 18, characterized in that it consists in making reacting a salt [R1SO2N = NSO2R2] -M ~ + with a halogenating agent, to obtain the precursor R1SO2N = NSOR2X (X being a halogen), then to condense said precursor on a sulfonamide R3SO2NH2 in the presence of a base, or on a derivative metallic sulfonamide such as R3SO2NLi2 or R3SO2NNa2, and perform an ion exchange to get the cation wish.
ionique est un composé selon la revendication 1. 32. Electrolyte consisting of an ionic compound in solution in a solvent, characterized in that the compound ionic is a compound according to claim 1.
oxyder partiellement ledit polymère pour créer des carbocations dont la charge est compensée par les anions d'un composé ionique, caractérisé en ce que le composé
ionique est un composé selon la revendication 1. 37. Method for doping a polymer consisting of partially oxidize said polymer to create carbocations whose charge is compensated by anions of an ionic compound, characterized in that the compound ionic is a compound according to claim 1.
selon la revendication 1 comme photoinitiateur source d'acide catalysant la réaction. 38. Process for the polymerization or crosslinking of monomers or prepolymers capable of reacting by cationic, characterized in that a compound is used according to claim 1 as a source photoinitiator of acid catalyzing the reaction.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002266643A CA2266643C (en) | 1997-07-25 | 1998-07-27 | Ionic compounds with delocalized anionic charge, their use as components of ionic conductors or catalyst |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2.211.465 | 1997-07-25 | ||
CA2211465 | 1997-07-25 | ||
CA002266643A CA2266643C (en) | 1997-07-25 | 1998-07-27 | Ionic compounds with delocalized anionic charge, their use as components of ionic conductors or catalyst |
PCT/FR1998/001663 WO1999005100A1 (en) | 1997-07-25 | 1998-07-27 | Ionic compounds with delocalized anionic charge, their use as components of ionic conductors or catalyst |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2266643A1 true CA2266643A1 (en) | 1999-02-04 |
CA2266643C CA2266643C (en) | 2009-11-17 |
Family
ID=29712965
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002266643A Expired - Lifetime CA2266643C (en) | 1997-07-25 | 1998-07-27 | Ionic compounds with delocalized anionic charge, their use as components of ionic conductors or catalyst |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2266643C (en) |
-
1998
- 1998-07-27 CA CA002266643A patent/CA2266643C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2266643C (en) | 2009-11-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20180727 |