DE69929420T2 - Homo- oder copolymeres Material auf der Basis von Sulfonylimiden, die eine polymerisierbare Gruppe enthalten - Google Patents
Homo- oder copolymeres Material auf der Basis von Sulfonylimiden, die eine polymerisierbare Gruppe enthalten Download PDFInfo
- Publication number
- DE69929420T2 DE69929420T2 DE69929420T DE69929420T DE69929420T2 DE 69929420 T2 DE69929420 T2 DE 69929420T2 DE 69929420 T DE69929420 T DE 69929420T DE 69929420 T DE69929420 T DE 69929420T DE 69929420 T2 DE69929420 T2 DE 69929420T2
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- carbon atoms
- electrolyte
- fluoroalkyl
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 25
- 229920001577 copolymer Polymers 0.000 title claims description 15
- 229920001519 homopolymer Polymers 0.000 title claims description 9
- 125000005463 sulfonylimide group Chemical group 0.000 title description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- -1 acrylyl Chemical group 0.000 claims description 35
- 239000003792 electrolyte Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000011159 matrix material Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 239000002861 polymer material Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 28
- 210000004027 cell Anatomy 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052744 lithium Inorganic materials 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910001416 lithium ion Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 229940021013 electrolyte solution Drugs 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Chemical group 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 2
- 229910013063 LiBF 4 Inorganic materials 0.000 description 2
- 229910013684 LiClO 4 Inorganic materials 0.000 description 2
- 229910013870 LiPF 6 Inorganic materials 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000011244 liquid electrolyte Substances 0.000 description 2
- 229940006487 lithium cation Drugs 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical group 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 1
- LBKMJZAKWQTTHC-UHFFFAOYSA-N 4-methyldioxolane Chemical compound CC1COOC1 LBKMJZAKWQTTHC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 229910018871 CoO 2 Inorganic materials 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 241000877463 Lanio Species 0.000 description 1
- 229910013528 LiN(SO2 CF3)2 Inorganic materials 0.000 description 1
- 229910013553 LiNO Inorganic materials 0.000 description 1
- 229910012465 LiTi Inorganic materials 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- 238000001461 argentometric titration Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005841 biaryl group Chemical group 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/04—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/08—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/18—Cells with non-aqueous electrolyte with solid electrolyte
- H01M6/181—Cells with non-aqueous electrolyte with solid electrolyte with polymeric electrolytes
-
- 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
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Secondary Cells (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Conductive Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US139374 | 1998-08-25 | ||
| US09/139,374 US6350545B2 (en) | 1998-08-25 | 1998-08-25 | Sulfonylimide compounds |
| PCT/US1999/001668 WO2000010969A1 (en) | 1998-08-25 | 1999-01-26 | Sulfonylimides and their use as conductive salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69929420D1 DE69929420D1 (de) | 2006-04-06 |
| DE69929420T2 true DE69929420T2 (de) | 2006-09-28 |
Family
ID=22486317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69929420T Expired - Lifetime DE69929420T2 (de) | 1998-08-25 | 1999-01-26 | Homo- oder copolymeres Material auf der Basis von Sulfonylimiden, die eine polymerisierbare Gruppe enthalten |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6350545B2 (enExample) |
| EP (1) | EP1107951B8 (enExample) |
| JP (1) | JP2003532619A (enExample) |
| KR (1) | KR100605075B1 (enExample) |
| AU (1) | AU2472399A (enExample) |
| CA (1) | CA2339627A1 (enExample) |
| DE (1) | DE69929420T2 (enExample) |
| WO (1) | WO2000010969A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69721748T2 (de) | 1996-12-30 | 2004-03-11 | Hydro-Québec, Montréal | Oberflächenmodifizierte kohlenstoffmaterialien |
| EP0968181B1 (fr) | 1997-12-01 | 2005-04-27 | Acep Inc. | Sels de sulfones perfluores, et leurs utilisations comme materiaux a conduction ionique |
| WO1999040025A1 (fr) * | 1998-02-03 | 1999-08-12 | Acep Inc. | Nouveaux materiaux utiles en tant que solutes electrolytiques |
| US20040115523A1 (en) * | 2001-02-14 | 2004-06-17 | Hayato Hommura | Non-aqueous electrolyte battery |
| WO2003036751A1 (en) * | 2001-10-25 | 2003-05-01 | Sanyo Electric Co.,Ltd. | Non-aqueous electrolyte secondary cell |
| JP4288400B2 (ja) * | 2001-11-15 | 2009-07-01 | 日本電気株式会社 | 二次電池用電解液の製造方法および二次電池用電解液、二次電池の製造方法および二次電池 |
| CN100577626C (zh) | 2002-03-25 | 2010-01-06 | 嘉吉有限公司 | 制造α,β-不饱和羧酸或其衍生物的方法 |
| 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 |
| JP2004200015A (ja) * | 2002-12-19 | 2004-07-15 | Sanyo Electric Co Ltd | 非水電池用電解質及びその製造方法並びに非水電池用電解液 |
| JP4465968B2 (ja) * | 2003-03-18 | 2010-05-26 | 日本電気株式会社 | 二次電池用電解液およびそれを用いた二次電池 |
| JP2005350525A (ja) * | 2004-06-09 | 2005-12-22 | Japan Carlit Co Ltd:The | 導電性ポリアニリン誘導体及びその組成物 |
| US7598002B2 (en) * | 2005-01-11 | 2009-10-06 | Material Methods Llc | Enhanced electrochemical cells with solid-electrolyte interphase promoters |
| JP5067522B2 (ja) * | 2005-04-08 | 2012-11-07 | ソニー株式会社 | 二次電池用電解液および二次電池 |
| JP2009504790A (ja) * | 2005-08-22 | 2009-02-05 | トランスファート プラス エスイーシー | スルホニルイミド及びその誘導体を調製するための方法 |
| JP4701923B2 (ja) * | 2005-08-26 | 2011-06-15 | トヨタ自動車株式会社 | イオン伝導材料およびその利用 |
| EP1941568A1 (en) * | 2005-09-26 | 2008-07-09 | Oxis Energy Limited | Lithium-sulphur battery with high specific energy |
| US20080286626A1 (en) * | 2007-05-18 | 2008-11-20 | Polyfuel, Inc. | Bis(aryl)sulfonimide functionalized ion conducting polymers |
| JP5379168B2 (ja) * | 2008-03-07 | 2013-12-25 | スリーエム イノベイティブ プロパティズ カンパニー | 帯電防止性ロックコポリマー感圧性接着剤及び物品 |
| JP4952693B2 (ja) * | 2008-09-25 | 2012-06-13 | ソニー株式会社 | 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 |
| JP2013030465A (ja) * | 2011-06-24 | 2013-02-07 | Central Glass Co Ltd | 非水電解液電池用電解液及び非水電解液電池 |
| US8636916B2 (en) * | 2011-08-30 | 2014-01-28 | Corning Incorporated | Electrolyte synthesis for ultracapacitors |
| JP5796417B2 (ja) | 2011-08-31 | 2015-10-21 | セントラル硝子株式会社 | 非水電解液電池用電解液及び非水電解液電池 |
| EP2629352A1 (en) | 2012-02-17 | 2013-08-21 | Oxis Energy Limited | Reinforced metal foil electrode |
| US8377406B1 (en) | 2012-08-29 | 2013-02-19 | Boulder Ionics Corporation | Synthesis of bis(fluorosulfonyl)imide |
| US9478828B2 (en) | 2012-12-04 | 2016-10-25 | Samsung Sdi Co., Ltd. | Electrolyte for rechargeable lithium battery and rechargeable lithium battery including the same |
| ES2546609T3 (es) | 2013-03-25 | 2015-09-25 | Oxis Energy Limited | Un método para cargar una celda de litio-azufre |
| EP2784850A1 (en) | 2013-03-25 | 2014-10-01 | Oxis Energy Limited | A method of cycling a lithium-sulphur cell |
| ES2671399T3 (es) | 2013-03-25 | 2018-06-06 | Oxis Energy Limited | Un método para cargar una celda de litio-azufre |
| GB2517228B (en) | 2013-08-15 | 2016-03-02 | Oxis Energy Ltd | Laminate cell |
| WO2015058116A1 (en) | 2013-10-17 | 2015-04-23 | Cargill, Incorporated | Methods for producing alkyl hydroxyalkanoates |
| US9899705B2 (en) | 2013-12-17 | 2018-02-20 | Oxis Energy Limited | Electrolyte for a lithium-sulphur cell |
| WO2015181527A1 (en) | 2014-05-30 | 2015-12-03 | Oxis Energy Limited | Lithium-sulphur cell |
| WO2016061356A1 (en) | 2014-10-17 | 2016-04-21 | Cargill, Incorporated | Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid |
| JP6366550B2 (ja) * | 2015-08-24 | 2018-08-01 | 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 |
| JP6401130B2 (ja) * | 2015-08-24 | 2018-10-03 | 信越化学工業株式会社 | 導電性ポリマー複合体及び基板 |
| US12107225B2 (en) * | 2018-03-27 | 2024-10-01 | Daikin Industries, Ltd. | Electrolyte solution, electrochemical device, lithium ion secondary battery, module and compound |
| 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 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791595A (fr) * | 1971-11-18 | 1973-05-17 | Omf California Inc | Electrolyte pour accumulateur |
| FR2606218A1 (fr) | 1986-10-30 | 1988-05-06 | Elf Aquitaine | Nouveau materiau a conduction ionique |
| US5273840A (en) * | 1990-08-01 | 1993-12-28 | Covalent Associates Incorporated | Methide salts, formulations, electrolytes and batteries formed therefrom |
| FR2673769B1 (fr) | 1991-03-07 | 1993-06-18 | Centre Nat Rech Scient | Materiaux polymeriques a conduction ionique. |
| EP0631340B1 (en) | 1993-06-18 | 2001-11-21 | Hitachi Maxell Ltd. | Organic electrolytic solution cell |
| US5538812A (en) * | 1994-02-04 | 1996-07-23 | Moltech Corporation | Electrolyte materials containing highly dissociated metal ion salts |
| JP3878206B2 (ja) | 1994-03-21 | 2007-02-07 | サントル・ナショナル・ドゥ・ラ・ルシェルシュ・シャンティフィク | 良好な耐食性を示すイオン性伝導材料 |
| 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 |
| JP3250777B2 (ja) | 1995-02-13 | 2002-01-28 | セントラル硝子株式会社 | イミド類、その塩類およびそれらの製造法 |
| US5514493A (en) * | 1995-03-06 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Perfluoroalkylsulfonates, sulfonimides, and sulfonyl methides, and electrolytes containing them |
| US6013393A (en) * | 1995-05-09 | 2000-01-11 | Ricoh Company, Ltd. | Ionic conductive polymer gel and lithium-ion battery using the same |
| US5691081A (en) * | 1995-09-21 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Battery containing bis(perfluoroalkylsulfonyl)imide and cyclic perfluoroalkylene disulfonylimide salts |
| US5573872A (en) * | 1995-11-22 | 1996-11-12 | Shackle; Dale R. | Solid electrolytes with novel electrolyte salts and electrolytic cells produced therefrom |
| FR2742437B1 (fr) * | 1995-12-14 | 1998-01-09 | Electricite De France | Bis(phenylsulfonyl)imidures, leur procede de preparation et materiaux a conduction ionique les comprenant |
| DE69721748T2 (de) * | 1996-12-30 | 2004-03-11 | Hydro-Québec, Montréal | Oberflächenmodifizierte kohlenstoffmaterialien |
| US6063522A (en) * | 1998-03-24 | 2000-05-16 | 3M Innovative Properties Company | Electrolytes containing mixed fluorochemical/hydrocarbon imide and methide salts |
-
1998
- 1998-08-25 US US09/139,374 patent/US6350545B2/en not_active Expired - Lifetime
-
1999
- 1999-01-26 JP JP2000566243A patent/JP2003532619A/ja active Pending
- 1999-01-26 EP EP99904298A patent/EP1107951B8/en not_active Expired - Lifetime
- 1999-01-26 WO PCT/US1999/001668 patent/WO2000010969A1/en not_active Ceased
- 1999-01-26 AU AU24723/99A patent/AU2472399A/en not_active Abandoned
- 1999-01-26 KR KR1020017002359A patent/KR100605075B1/ko not_active Expired - Fee Related
- 1999-01-26 CA CA002339627A patent/CA2339627A1/en not_active Abandoned
- 1999-01-26 DE DE69929420T patent/DE69929420T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1107951B1 (en) | 2006-01-11 |
| WO2000010969A1 (en) | 2000-03-02 |
| DE69929420D1 (de) | 2006-04-06 |
| JP2003532619A (ja) | 2003-11-05 |
| KR100605075B1 (ko) | 2006-07-26 |
| EP1107951A1 (en) | 2001-06-20 |
| AU2472399A (en) | 2000-03-14 |
| EP1107951B8 (en) | 2006-05-03 |
| US20010008736A1 (en) | 2001-07-19 |
| CA2339627A1 (en) | 2000-03-02 |
| US6350545B2 (en) | 2002-02-26 |
| KR20030063495A (ko) | 2003-07-31 |
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| 8364 | No opposition during term of opposition |