JP7216673B2 - イミダゾール誘導体を含むポリマーおよび電気化学セルにおけるそれらの使用 - Google Patents
イミダゾール誘導体を含むポリマーおよび電気化学セルにおけるそれらの使用 Download PDFInfo
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- JP7216673B2 JP7216673B2 JP2019572388A JP2019572388A JP7216673B2 JP 7216673 B2 JP7216673 B2 JP 7216673B2 JP 2019572388 A JP2019572388 A JP 2019572388A JP 2019572388 A JP2019572388 A JP 2019572388A JP 7216673 B2 JP7216673 B2 JP 7216673B2
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- 229920000642 polymer Polymers 0.000 title claims description 251
- 150000002460 imidazoles Chemical class 0.000 title description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
- -1 substituted Chemical class 0.000 claims description 76
- 239000003792 electrolyte Substances 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 239000007772 electrode material Substances 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 239000011230 binding agent Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 35
- 229920001577 copolymer Polymers 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000011262 electrochemically active material Substances 0.000 claims description 20
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical class C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 claims description 14
- 229920001400 block copolymer Polymers 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 125000005647 linker group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 13
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 12
- 229920001519 homopolymer Polymers 0.000 claims description 12
- 229920002125 Sokalan® Polymers 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229920005604 random copolymer Polymers 0.000 claims description 11
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 10
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 10
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000005518 polymer electrolyte Substances 0.000 claims description 9
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910001416 lithium ion Inorganic materials 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 239000005060 rubber Substances 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 229920000459 Nitrile rubber Polymers 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 239000002033 PVDF binder Substances 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000011258 core-shell material Substances 0.000 claims description 3
- 229920005558 epichlorohydrin rubber Polymers 0.000 claims description 3
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000011245 gel electrolyte Substances 0.000 claims description 3
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
- 239000011118 polyvinyl acetate Substances 0.000 claims description 3
- 239000003232 water-soluble binding agent Substances 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002322 conducting polymer Substances 0.000 claims description 2
- 229920001940 conductive polymer Polymers 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 101
- 239000000243 solution Substances 0.000 description 22
- ZOCKVPYUHQDWAU-UHFFFAOYSA-N 2-ethenyl-1h-imidazole-4,5-dicarbonitrile Chemical compound C=CC1=NC(C#N)=C(C#N)N1 ZOCKVPYUHQDWAU-UHFFFAOYSA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
- 230000014759 maintenance of location Effects 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- 238000007334 copolymerization reaction Methods 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000010406 cathode material Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 239000011149 active material Substances 0.000 description 8
- 239000010405 anode material Substances 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000002174 Styrene-butadiene Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- 238000001453 impedance spectrum Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000157 electrochemical-induced impedance spectroscopy Methods 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920005596 polymer binder Polymers 0.000 description 5
- 239000002491 polymer binding agent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000012987 RAFT agent Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004891 communication Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000005518 electrochemistry Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 3
- AISZNMCRXZWVAT-UHFFFAOYSA-N 2-ethylsulfanylcarbothioylsulfanyl-2-methylpropanenitrile Chemical compound CCSC(=S)SC(C)(C)C#N AISZNMCRXZWVAT-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052493 LiFePO4 Inorganic materials 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000012661 block copolymerization Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 239000011244 liquid electrolyte Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910001463 metal phosphate Inorganic materials 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- ONXYMIIQXBMPMD-UHFFFAOYSA-N C(CCCCCCCCCCC)SC(=S)SC(C(=O)OCC(COC(C(C)(C)SC(=S)SCCCCCCCCCCCC)=O)(COC(C(C)(C)SC(=S)SCCCCCCCCCCCC)=O)COC(C(C)(C)SC(=S)SCCCCCCCCCCCC)=O)(C)C Chemical compound C(CCCCCCCCCCC)SC(=S)SC(C(=O)OCC(COC(C(C)(C)SC(=S)SCCCCCCCCCCCC)=O)(COC(C(C)(C)SC(=S)SCCCCCCCCCCCC)=O)COC(C(C)(C)SC(=S)SCCCCCCCCCCCC)=O)(C)C ONXYMIIQXBMPMD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910002986 Li4Ti5O12 Inorganic materials 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- LAKYXBYUROTWBI-UHFFFAOYSA-N bis(benzylsulfanyl)methanethione Chemical compound C=1C=CC=CC=1CSC(=S)SCC1=CC=CC=C1 LAKYXBYUROTWBI-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 159000000003 magnesium salts Chemical group 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- DZFGVGDQHQHOKZ-UHFFFAOYSA-N 2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoic acid Chemical compound CCCCCCCCCCCCSC(=S)SC(C)(C)C(O)=O DZFGVGDQHQHOKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
- 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 229910007848 Li2TiO3 Inorganic materials 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910010941 LiFSI Inorganic materials 0.000 description 1
- 229910014616 LiMnFePO4 Inorganic materials 0.000 description 1
- 229910000668 LiMnPO4 Inorganic materials 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- 229910001290 LiPF6 Inorganic materials 0.000 description 1
- 229910012946 LiV2O5 Inorganic materials 0.000 description 1
- 229910012970 LiV3O8 Inorganic materials 0.000 description 1
- 229910002097 Lithium manganese(III,IV) oxide Inorganic materials 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
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Images
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
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- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0065—Solid electrolytes
- H01M2300/0082—Organic polymers
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- H—ELECTRICITY
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- H01M2300/00—Electrolytes
- H01M2300/0085—Immobilising or gelification of electrolyte
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- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
- H01M4/5825—Oxygenated metallic salts or polyanionic structures, e.g. borates, phosphates, silicates, olivines
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- 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
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| US62/529,146 | 2017-07-06 | ||
| PCT/CA2018/050830 WO2019006560A1 (en) | 2017-07-06 | 2018-07-06 | Polymers comprising imidazole derivatives and their use in electrochemical cells |
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| KR102275863B1 (ko) * | 2018-04-04 | 2021-07-12 | 주식회사 엘지에너지솔루션 | 리튬 이차 전지용 전극 및 이를 포함하는 리튬 이차 전지 |
| CN111987361A (zh) * | 2020-08-17 | 2020-11-24 | 仲恺农业工程学院 | 一种咪唑类聚离子液体电解质及其制备方法和应用 |
| KR20220067042A (ko) * | 2020-11-17 | 2022-05-24 | 현대자동차주식회사 | 고분자 전해질, 및 이의 제조방법 |
| CN113571773B (zh) * | 2021-06-23 | 2024-02-23 | 惠州锂威新能源科技有限公司 | 一种锂离子电池电解液及含该电解液的锂离子电池 |
| US12438195B2 (en) | 2021-07-29 | 2025-10-07 | Lg Energy Solution, Ltd. | Non-aqueous electrolyte, and lithium secondary battery comprising the same |
| KR102598513B1 (ko) * | 2022-10-27 | 2023-11-06 | 제이엘켐 주식회사 | 이미다졸륨 관능기 함유 이차 전지 전극용 바인더 수지, 이차 전지용 음극 및 이차 전지 |
| JP2025018838A (ja) * | 2023-07-27 | 2025-02-06 | 三井化学株式会社 | 電極用組成物、電極及び電池 |
| FR3152279A1 (fr) * | 2023-08-24 | 2025-02-28 | Snf Sa | Polymere hydrosoluble comme liant pour batterie |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005322555A (ja) | 2004-04-08 | 2005-11-17 | Sony Corp | イオン伝導体及びその製造方法、並びに電気化学デバイス |
| CN102020748A (zh) | 2009-09-17 | 2011-04-20 | 中国科学院化学研究所 | 聚合物-金属离子络合物凝胶电解质及其制备方法与应用 |
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| US3449123A (en) * | 1964-09-08 | 1969-06-10 | Fuji Photo Film Co Ltd | Color turbidity agent in color photographic materials |
| US3935086A (en) * | 1975-02-13 | 1976-01-27 | Asahi Kasei Kogyo Kabushiki Kaisha | Electrodialysis process |
| DE2506085C3 (de) * | 1975-02-13 | 1982-04-15 | Asahi Kasei Kogyo K.K., Osaka | Anionenaustauschermembran, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE3018131A1 (de) * | 1980-05-12 | 1981-11-19 | Basf Ag, 6700 Ludwigshafen | Polyisocyanate enthaltende haftkleber |
| US4299939A (en) * | 1980-06-30 | 1981-11-10 | American Cyanamid Company | Homopolymers and copolymers of 2-alkenylimidazole or its 1,3-dialkyl-2-alkenylimidazolium salts |
| JP3700992B2 (ja) * | 1997-05-26 | 2005-09-28 | 株式会社トクヤマ | 陰イオン交換樹脂の製造方法 |
| JPH11260407A (ja) | 1998-03-16 | 1999-09-24 | Mitsubishi Paper Mills Ltd | リチウム2次電池用高分子電解質 |
| US6624270B1 (en) * | 2000-01-14 | 2003-09-23 | The Regents Of The University Of Michigan | Copolymers derived from vinyl dicyanoimidazoles and other monomers |
| EP1388906A3 (en) | 2002-08-05 | 2006-10-11 | Nec Tokin Corporation | Cell electrode and electrochemical cell therewith |
| US20060204813A1 (en) | 2003-07-28 | 2006-09-14 | Takuro Hirakimoto | Ionic conductor, method of manufacturing the same, and electrochemical device |
| US9379368B2 (en) * | 2011-07-11 | 2016-06-28 | California Institute Of Technology | Electrochemical systems with electronically conductive layers |
| WO2013084116A1 (de) * | 2011-12-07 | 2013-06-13 | Basf Se | Elektrochemische zellen umfassend stickstoff-haltige polymere |
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| CN102867648B (zh) * | 2012-09-14 | 2015-10-28 | 华东师范大学 | 含乙烯基咪唑链段聚合物凝胶电解质及其制备方法和应用 |
| JP5965824B2 (ja) * | 2012-11-26 | 2016-08-10 | 積水化学工業株式会社 | 後硬化テープ及び接合部材の接合方法 |
| JP2015017153A (ja) * | 2013-07-09 | 2015-01-29 | 積水化学工業株式会社 | 後硬化テープ及び接合部材の接合方法 |
| KR102592691B1 (ko) * | 2015-04-03 | 2023-10-24 | 삼성전자주식회사 | 리튬이차전지용 전해질 및 이를 포함하는 리튬이차전지 |
| JP6613818B2 (ja) * | 2015-10-30 | 2019-12-04 | 東洋インキScホールディングス株式会社 | 感圧式接着剤及び感圧式接着フィルム |
| CN106336480B (zh) * | 2016-08-23 | 2018-07-06 | 中国石油化工股份有限公司 | 用于改善高含蜡稠油低温流动性能的添加剂 |
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| JP2005322555A (ja) | 2004-04-08 | 2005-11-17 | Sony Corp | イオン伝導体及びその製造方法、並びに電気化学デバイス |
| CN102020748A (zh) | 2009-09-17 | 2011-04-20 | 中国科学院化学研究所 | 聚合物-金属离子络合物凝胶电解质及其制备方法与应用 |
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| CN111065658A (zh) | 2020-04-24 |
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| US11643497B2 (en) | 2023-05-09 |
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