JPWO2019167875A1 - 有機硫黄系電極活物質 - Google Patents
有機硫黄系電極活物質 Download PDFInfo
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- JPWO2019167875A1 JPWO2019167875A1 JP2020503488A JP2020503488A JPWO2019167875A1 JP WO2019167875 A1 JPWO2019167875 A1 JP WO2019167875A1 JP 2020503488 A JP2020503488 A JP 2020503488A JP 2020503488 A JP2020503488 A JP 2020503488A JP WO2019167875 A1 JPWO2019167875 A1 JP WO2019167875A1
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- 239000007772 electrode material Substances 0.000 title claims abstract description 54
- 125000001741 organic sulfur group Chemical group 0.000 title claims abstract description 37
- 229920002239 polyacrylonitrile Polymers 0.000 claims abstract description 78
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 70
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 55
- 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 claims abstract description 48
- 239000011734 sodium Substances 0.000 claims abstract description 48
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 48
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000011591 potassium Substances 0.000 claims abstract description 45
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 45
- 239000011255 nonaqueous electrolyte Substances 0.000 claims abstract description 42
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 37
- 239000011593 sulfur Substances 0.000 claims abstract description 37
- 229910052742 iron Inorganic materials 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 25
- 239000012298 atmosphere Substances 0.000 claims description 16
- 230000001590 oxidative effect Effects 0.000 claims description 13
- -1 aromatic ring compound Chemical class 0.000 description 94
- 150000001875 compounds Chemical class 0.000 description 88
- 238000000034 method Methods 0.000 description 39
- 238000010438 heat treatment Methods 0.000 description 35
- 150000002894 organic compounds Chemical class 0.000 description 26
- 239000002994 raw material Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 17
- 229910052744 lithium Inorganic materials 0.000 description 17
- 239000002002 slurry Substances 0.000 description 17
- 239000002245 particle Substances 0.000 description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000003792 electrolyte Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000011295 pitch Substances 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- 239000010936 titanium Substances 0.000 description 10
- 229910052723 transition metal Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229910052759 nickel Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 6
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000011245 gel electrolyte Substances 0.000 description 6
- 229910001416 lithium ion Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Chemical group 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 229910000838 Al alloy Inorganic materials 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 239000002033 PVDF binder Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000007606 doctor blade method Methods 0.000 description 5
- 229910052732 germanium Inorganic materials 0.000 description 5
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000002905 metal composite material Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 5
- 239000007774 positive electrode material Substances 0.000 description 5
- 150000003112 potassium compounds Chemical class 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 150000003388 sodium compounds Chemical class 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 101100350964 Arabidopsis thaliana PANS1 gene Proteins 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229910013870 LiPF 6 Inorganic materials 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 235000003891 ferrous sulphate Nutrition 0.000 description 4
- 239000011790 ferrous sulphate Substances 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 4
- 239000011244 liquid electrolyte Substances 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000004570 mortar (masonry) Substances 0.000 description 4
- 239000007773 negative electrode material Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- 239000005518 polymer electrolyte Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 4
- 239000007784 solid electrolyte Substances 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229910004283 SiO 4 Inorganic materials 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000006230 acetylene black Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000002134 carbon nanofiber Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910003480 inorganic solid Inorganic materials 0.000 description 3
- 150000002506 iron compounds Chemical class 0.000 description 3
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 239000005968 1-Decanol Substances 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
(式中、*は結合手を表す)
これらを用いたアクリロニトリルの重合方法は公知の重合方法で構わない。
導電助剤の平均粒子径は、0.0001μm〜100μmであることが好ましく、0.01μm〜50μmであることがより好ましい。
液体電解質及び高分子ゲル電解質における、電解質の含有量は、好ましくは0.5〜7mol/L、より好ましくは0.8〜1.8mol/Lである。
前記アマイド化合物としては、N−メチルピロリドン、ジメチルホルムアミド、ジメチルアセトアミド等が挙げられる。
攪拌機、温度計、冷却管及び窒素ガス導入管を装備したガラス製反応容器に、アクリロニトリル100質量部、脱イオン水500質量部、過硫酸ナトリウム0.6質量部、亜硫酸水素ナトリウム0.9質量部、硫酸第一鉄0.000012質量部を仕込み、硫酸でpH3に調整した。窒素置換後に60℃まで昇温し、60℃で4時間攪拌を続けた。生成したポリアクリロニトリルの沈殿を、20質量倍の水に入れ、50℃で1時間撹拌した後、ろ過し、乾燥した。乾燥したポリアクリロニトリルを、乳鉢を用いて粉砕し、開口径30μmのふるいを用いて、大きな粒子を除き、ポリアクリロニトリルA1を得た。
製造例1の過硫酸ナトリウムを過硫酸カリウムに変更した以外は、製造例1と同様の操作を行い、ポリアクリロニトリルA2を得た。
製造例1の過硫酸ナトリウムを過硫酸カリウムに、亜硫酸水素ナトリウムを亜硫酸水素カリウムに変更した以外は、製造例1と同様の操作を行い、ポリアクリロニトリルA3を得た。
製造例1の過硫酸ナトリウムを過硫酸アンモニウムに変更した以外は、製造例1と同様の操作を行い、ポリアクリロニトリルA4を得た。
製造例1の亜硫酸水素ナトリウムを亜硫酸水素アンモニウムに変更した以外は、製造例1と同様の操作を行い、ポリアクリロニトリルA5を得た。
攪拌機、温度計、冷却管及び窒素ガス導入管を装備したガラス製反応容器に、アクリロニトリル100質量部、ジメチルスルホキシド371質量部、アゾビスイソブチロニトリル0.4質量部を仕込み、窒素置換後に65℃で5時間、75℃で7時間加熱して重合した。この後、減圧して未反応のアクリロニトリルを除去し、ステアリン酸ナトリウム(東栄化学工業製、商品名NA−ST)0.85質量部及びナフテン酸鉄(東栄化学工業製、商品名ナフテン酸鉄5%)0.014質量部を添加して、ポリアクリロニトリルのジメチルスルホキシド溶液を得た。この溶液を直径0.08mmのノズルから水中に押出して得られた繊維状のポリアクリロニトリルを5mm程度に切断してから、20質量倍の水に入れ、90℃で1時間撹拌した後、ろ過し、乾燥して、ポリアクリロニトリルA6を得た。
ナフテン酸鉄を添加しなかった以外は、製造例6と同様の操作を行い、ポリアクリロニトリルA7を得た。
製造例1の硫酸第一鉄の量を0.000012質量部から0.000003質量部に変更した以外は、製造例1と同様の操作を行い、ポリアクリロニトリルA8を得た。
製造例1の過硫酸ナトリウムを過硫酸アンモニウムに、亜硫酸水素ナトリウムを亜硫酸水素アンモニウムに変更した以外は、製造例1と同様の操作を行い、ポリアクリロニトリルA9を得た。
ステアリン酸ナトリウム及びナフテン酸鉄を添加しなかった以外は、製造例6と同様の操作を行い、ポリアクリロニトリルA10を得た。
ステアリン酸ナトリウムの量を、0.45質量部から0.05質量部に変更した以外は、製造例6と同様の操作を行い、ポリアクリロニトリルA11を得た。
攪拌機、温度計、冷却管及び窒素ガス導入管を装備したガラス製反応容器に、アクリロニトリル100質量部、脱イオン水500質量部、過硫酸ナトリウム3.4質量部、亜硫酸水素ナトリウム1.3質量部を仕込み、硫酸でpH3に調整した。窒素置換後に、40℃まで昇温し、40℃で5時間撹拌を続けた。生成したポリアクリロニトリルの沈殿を、20質量倍の水に入れ、50℃で1時間撹拌した後、ろ過し、乾燥した。乾燥したポリアクリロニトリルを、乳鉢を用いて粉砕し、開口径30μmのふるいを用いて、大きな粒子を除き、ポリアクリロニトリルA12を得た。
攪拌機、温度計、冷却管、滴下管及び窒素ガス導入管を装備したガラス製反応容器に、脱イオン水600質量部、アクリロニトリル100質量部、アニオン系界面活性剤ジオクチルスルホコハク酸ナトリウム(株式会社ADEKA製、商品名アデカコールEC−4500)6質量部、過硫酸ナトリウム0.3質量部を仕込み、硫酸でpH3に調整した。窒素置換後に、55℃まで昇温し、アクリロニトリル200質量部を90分かけて滴下し、滴下終了後、80℃に昇温し5時間撹拌を続けた。生成したポリアクリロニトリルの沈殿を、20質量倍の水に入れ、50℃で1時間撹拌した後、ろ過し、乾燥した。乾燥したポリアクリロニトリルを、乳鉢を用いて粉砕し、開口径30μmのふるいを用いて、大きな粒子を除き、ポリアクリロニトリルA13を得た。
10質量部のポリアクリロニトリルA1と30質量部の硫黄粉末(シグマアルドリッチ製、平均粒子径200μm)を、乳鉢を用いて混合した。特開2013−054957の実施例に準じて、この混合物を有底円筒状ガラス管に収容したのち、ガラス管の下部をルツボ型電気炉に入れ、窒素気流下に発生する硫化水素を除去しながら400℃で1時間加熱した。冷却後、生成物をガラスチューブオーブンに入れ、真空吸引しつつ250℃で3時間加熱することにより単体硫黄を除去した。得られた硫黄変性生成物を、ボールミルを用いて粉砕後、ふるいで分級し平均粒子径が10μmの硫黄変性ポリアクリロニトリルのPANS1を得た。
ポリアクリロニトリルA1の代わりに、ポリアクリロニトリルA2〜A13を用いた以外は実施例1と同様の操作を行い、PANS2〜13を得た。
PANS1〜PANS13の硫黄変性ポリアクリロニトリルを用いて、下記の方法で実施例2〜9、比較例1〜5の電極を作製した。
電極活物質として硫黄変性ポリアクリロニトリル92.0質量部、導電助剤としてアセチレンブラック(電気化学工業製)3.5質量部、及びカーボンナノチューブ(昭和電工製、商品名VGCF)1.5質量部、バインダーとしてスチレン−ブタジエンゴム(水分散液、日本ゼオン製)1.5質量部及びカルボキシメチルセルロース(ダイセルファインケム製)1.5質量部、並びに溶剤として水120質量部を、自転・公転ミキサーを用いて混合しスラリーを調製した。このスラリー組成物を、ドクターブレード法によりステンレス箔(厚さ20μm)の集電体に塗布し、90℃で3時間乾燥した。その後、この電極を所定の大きさにカットし、120℃で2時間真空乾燥を行い、円盤状電極を作製した。
正極活物質としてLi(Ni1/3Co1/3Mn1/3)O2(日本化学産業製、商品名:NCM111)90.0質量部、導電助剤としてアセチレンブラック(電気化学工業製)5.0質量部、バインダーとしてポリフッ化ビニリデン(クレハ製)5.0質量部、及び溶媒としてN−メチルピロリドン100質量部を、自転・公転ミキサーを用いて混合しスラリーを調製した。このスラリー組成物を、ドクターブレード法によりアルミニウム箔(厚さ20μm)の集電体に塗布し、90℃で3時間乾燥した。その後、この電極を所定の大きさにカットし、120℃で2時間真空乾燥を行い、円盤状の正極1を作製した。
厚さ500μmのリチウム金属を所定の大きさにカットし、円盤状の負極1を作製した。
エチレンカーボネート50体積%、ジエチルカーボネート50体積%からなる混合溶媒に、LiPF6を1.0mol/Lの濃度で溶解し電解質溶液を調製した。
実施例2〜9及び比較例1〜5の電極を正極、負極1を負極とし、セパレータとしてガラスフィルターを挟んでケース内に保持した。その後、先に調製した非水電解質をケース内に注入し、ケースを密閉、封止して、実施例10〜17及び比較例6〜10の非水電解質二次電池(φ20mm、厚さ3.2mmのコイン型)を製作した。
また、実施例2〜9及び比較例1〜5の電極を負極、正極1を負極とし、セパレータとしてガラスフィルターを挟んでケース内に保持した。その後、先に調製した非水電解質をケース内に注入し、ケースを密閉、封止して、実施例18〜25及び比較例11〜15の非水電解質二次電池(φ20mm、厚さ3.2mmのコイン型)を製作した。
非水電解質二次電池を25℃の恒温槽に入れ、充電終止電圧を3.0V、放電終止電圧を1.0Vとし、充電レート0.1C、放電レート0.1Cの充放電を5サイクル、次いで充電レート1C、放電レート1Cの充放電を5サイクル、計10サイクルの充放電を行い、各サイクルの充電容量と放電容量(単位:mAh/g)を測定した。
1サイクル目の、充電容量に対する放電容量の比を初回効率(%)、5サイクル目の放電容量に対する10サイクル目の放電容量の割合を容量維持率(%)とした。結果を表3及び4に示す。
1a 正極集電体
2 負極
2a 負極集電体
3 電解液
4 正極ケース
5 負極ケース
6 ガスケット
7 セパレータ
10 コイン型の非水電解質二次電池
10’円筒型の非水電解質二次電池
11 負極
12 負極集電体
13 正極
14 正極集電体
15 電解液
16 セパレータ
17 正極端子
18 負極端子
19 負極板
20 負極リード
21 正極板
22 正極リード
23 ケース
24 絶縁板
25 ガスケット
26 安全弁
27 PTC素子
Claims (8)
- ナトリウムとカリウムの含量の合計が100質量ppm〜1000質量ppmである有機硫黄系電極活物質。
- 更に、鉄の含量が1質量ppm〜20質量ppmである請求項1に記載の有機硫黄系電極活物質。
- 硫黄の含量が25質量%〜60質量%である請求項1又は2に記載の有機硫黄系電極活物質。
- 有機硫黄系電極活物質が硫黄変性ポリアクリロニトリルである請求項1〜3のいずれか1項に記載の有機硫黄系電極活物質。
- 請求項1〜4のいずれか1項に記載の有機硫黄系電極活物質を電極活物質とする二次電池用電極。
- 請求項5に記載の二次電池用電極を正極とする非水電解質二次電池。
- 請求項5に記載の二次電池用電極を負極とする非水電解質二次電池。
- ナトリウムとカリウムの含量の合計が126質量ppm〜2360質量ppmであるポリアクリロニトリルと単体硫黄との混合物を非酸化性雰囲気中で加熱処理する工程を有する、ナトリウムとカリウムの含量の合計が100質量ppm〜1000質量ppmである硫黄変性ポリアクリロニトリルの製造方法。
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US20200350587A1 (en) | 2020-11-05 |
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