WO2019009135A1 - 樹脂組成物、積層体およびその製造方法、電極、二次電池ならびに電気二重層キャパシタ - Google Patents
樹脂組成物、積層体およびその製造方法、電極、二次電池ならびに電気二重層キャパシタ Download PDFInfo
- Publication number
- WO2019009135A1 WO2019009135A1 PCT/JP2018/024115 JP2018024115W WO2019009135A1 WO 2019009135 A1 WO2019009135 A1 WO 2019009135A1 JP 2018024115 W JP2018024115 W JP 2018024115W WO 2019009135 A1 WO2019009135 A1 WO 2019009135A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- resin
- group
- composition according
- integer
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 99
- 239000003990 capacitor Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000011347 resin Substances 0.000 claims abstract description 119
- 229920005989 resin Polymers 0.000 claims abstract description 119
- 239000000945 filler Substances 0.000 claims abstract description 70
- 125000000524 functional group Chemical group 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000002378 acidificating effect Effects 0.000 claims abstract description 19
- 229920001721 polyimide Polymers 0.000 claims abstract description 19
- 150000007514 bases Chemical class 0.000 claims abstract description 16
- 239000004642 Polyimide Substances 0.000 claims abstract description 15
- 229920002577 polybenzoxazole Polymers 0.000 claims abstract description 11
- 239000004962 Polyamide-imide Substances 0.000 claims abstract description 10
- 229920002312 polyamide-imide Polymers 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 239000007787 solid Substances 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000000962 organic group Chemical group 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052718 tin Inorganic materials 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 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 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 51
- 239000011230 binding agent Substances 0.000 abstract description 22
- 230000007774 longterm Effects 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 description 51
- 238000003786 synthesis reaction Methods 0.000 description 51
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 39
- 239000010408 film Substances 0.000 description 35
- 150000004985 diamines Chemical class 0.000 description 24
- -1 imidazole compound Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000126 substance Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000002002 slurry Substances 0.000 description 15
- 230000003993 interaction Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000012086 standard solution Substances 0.000 description 12
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 229910001416 lithium ion Inorganic materials 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 125000004427 diamine group Chemical group 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011149 active material Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000011888 foil Substances 0.000 description 8
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000007773 negative electrode material Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 description 6
- 239000002033 PVDF binder Substances 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 229910021538 borax Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- 239000009719 polyimide resin Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 239000004328 sodium tetraborate Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 3
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006230 acetylene black Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 229910021393 carbon nanotube Inorganic materials 0.000 description 3
- 239000002041 carbon nanotube Substances 0.000 description 3
- 239000002482 conductive additive Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- FCSSPCOFDUKHPV-UHFFFAOYSA-N 2-Propenyl propyl disulfide Chemical compound CCCSSCC=C FCSSPCOFDUKHPV-UHFFFAOYSA-N 0.000 description 2
- KYACBXOQPZLDPV-UHFFFAOYSA-N 2-amino-4-(3-amino-4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(S(=O)(=O)C=2C=C(N)C(C(O)=O)=CC=2)=C1 KYACBXOQPZLDPV-UHFFFAOYSA-N 0.000 description 2
- DLLQVJOXCPRYAP-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C(N)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(N)=C1 DLLQVJOXCPRYAP-UHFFFAOYSA-N 0.000 description 2
- BBMYWMOZTWNHNL-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C(C(O)=O)=C1 BBMYWMOZTWNHNL-UHFFFAOYSA-N 0.000 description 2
- HSPUJPOVWDGDJF-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(N)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(N)C(C(O)=O)=C1 HSPUJPOVWDGDJF-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 description 2
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 2
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-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
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- JYCTWJFSRDBYJX-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3a,4,5,9b-tetrahydrobenzo[e][2]benzofuran-1,3-dione Chemical compound O=C1OC(=O)CC1C1C2=CC=CC=C2C(C(=O)OC2=O)C2C1 JYCTWJFSRDBYJX-UHFFFAOYSA-N 0.000 description 2
- DGQOZCNCJKEVOA-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1CC(=O)OC1=O DGQOZCNCJKEVOA-UHFFFAOYSA-N 0.000 description 2
- QVEIRZNRYOJFCL-UHFFFAOYSA-N 6053-46-9 Chemical compound O=C1OC(=O)C2CC1C1C2CC(=O)OC1=O QVEIRZNRYOJFCL-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- LDSODIRWGRCZQO-UHFFFAOYSA-N NC=1C=C(C=C(C=1)C(=O)O)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC(=C1)C(=O)O)N Chemical compound NC=1C=C(C=C(C=1)C(=O)O)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC(=C1)C(=O)O)N LDSODIRWGRCZQO-UHFFFAOYSA-N 0.000 description 2
- GKPXEEVDGJRKLX-UHFFFAOYSA-N NC=1C=C(C=C(C=1)C(=O)O)C(C)(C)C1=CC(=CC(=C1)C(=O)O)N Chemical compound NC=1C=C(C=C(C=1)C(=O)O)C(C)(C)C1=CC(=CC(=C1)C(=O)O)N GKPXEEVDGJRKLX-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 2
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910000625 lithium cobalt oxide Inorganic materials 0.000 description 2
- BFZPBUKRYWOWDV-UHFFFAOYSA-N lithium;oxido(oxo)cobalt Chemical compound [Li+].[O-][Co]=O BFZPBUKRYWOWDV-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001139 pH measurement Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 description 2
- GANDVAJEIJXBQJ-UHFFFAOYSA-M potassium;hydron;2-hydroxy-2-oxoacetate Chemical compound [K+].OC(=O)C(O)=O.OC(=O)C([O-])=O GANDVAJEIJXBQJ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005011 time of flight secondary ion mass spectroscopy Methods 0.000 description 2
- 238000002042 time-of-flight secondary ion mass spectrometry Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- VFFRLRQQWXGEBX-UHFFFAOYSA-N 1-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C=CC2=C1 VFFRLRQQWXGEBX-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- OZAAEETZNZUQRX-UHFFFAOYSA-N 1-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=C(S)C(C(=O)O)=CC=C21 OZAAEETZNZUQRX-UHFFFAOYSA-N 0.000 description 1
- YJGUVTBNQCVSQB-UHFFFAOYSA-N 2,2-diphenylpropanedioic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(C(=O)O)C1=CC=CC=C1 YJGUVTBNQCVSQB-UHFFFAOYSA-N 0.000 description 1
- CZROPTCHPNIDTD-UHFFFAOYSA-N 2-(1,1,1,3,3,3-hexafluoropropan-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(C(F)(F)F)C(F)(F)F CZROPTCHPNIDTD-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- CZSLBAPYTZUENY-UHFFFAOYSA-N 2-amino-4-(3-amino-4-carboxyphenoxy)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(OC=2C=C(N)C(C(O)=O)=CC=2)=C1 CZSLBAPYTZUENY-UHFFFAOYSA-N 0.000 description 1
- KECOIASOKMSRFT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)C=2C=C(N)C(O)=CC=2)=C1 KECOIASOKMSRFT-UHFFFAOYSA-N 0.000 description 1
- ZTZLVQYRXBHWEU-UHFFFAOYSA-N 2-amino-4-[1-(3-amino-4-hydroxyphenyl)-9h-fluoren-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C=2C(=C3C(C4=CC=CC=C4C3)=CC=2)C=2C=C(N)C(O)=CC=2)=C1 ZTZLVQYRXBHWEU-UHFFFAOYSA-N 0.000 description 1
- GPWZWWICAGSVPI-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(C(C=2C=C(N)C(C(O)=O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 GPWZWWICAGSVPI-UHFFFAOYSA-N 0.000 description 1
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 1
- UHIDYCYNRPVZCK-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C)(C)C1=CC=C(O)C(N)=C1 UHIDYCYNRPVZCK-UHFFFAOYSA-N 0.000 description 1
- IGIDZGNPFWGICD-UHFFFAOYSA-N 2-amino-4-phenylphenol Chemical group C1=C(O)C(N)=CC(C=2C=CC=CC=2)=C1 IGIDZGNPFWGICD-UHFFFAOYSA-N 0.000 description 1
- KHAFBBNQUOEYHB-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(O)=C1 KHAFBBNQUOEYHB-UHFFFAOYSA-N 0.000 description 1
- IYOLSZYAAACSNO-UHFFFAOYSA-N 2-amino-5-[1-(4-amino-3-hydroxyphenyl)-9H-fluoren-2-yl]phenol Chemical compound NC1=C(C=C(C=C1)C1=C(C=2CC3=CC=CC=C3C=2C=C1)C1=CC(=C(C=C1)N)O)O IYOLSZYAAACSNO-UHFFFAOYSA-N 0.000 description 1
- ZDRNVPNSQJRIRN-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C(O)=C1 ZDRNVPNSQJRIRN-UHFFFAOYSA-N 0.000 description 1
- JDFAWEKPFLGRAK-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(N)C(O)=CC=1C(C)(C)C1=CC=C(N)C(O)=C1 JDFAWEKPFLGRAK-UHFFFAOYSA-N 0.000 description 1
- ILGJVPVZCNNBKI-UHFFFAOYSA-N 2-amino-5-phenylphenol Chemical group C1=C(O)C(N)=CC=C1C1=CC=CC=C1 ILGJVPVZCNNBKI-UHFFFAOYSA-N 0.000 description 1
- UZSDRHVOBLQYCX-UHFFFAOYSA-N 2-amino-6-hydroxybenzoic acid Chemical compound NC1=CC=CC(O)=C1C(O)=O UZSDRHVOBLQYCX-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CXOWHCCVISNMIX-UHFFFAOYSA-N 2-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(N)=CC=C21 CXOWHCCVISNMIX-UHFFFAOYSA-N 0.000 description 1
- BSZMQMCPMFBCJT-UHFFFAOYSA-N 2-aminonaphthalene-1-thiol Chemical compound C1=CC=CC2=C(S)C(N)=CC=C21 BSZMQMCPMFBCJT-UHFFFAOYSA-N 0.000 description 1
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical compound NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- CDOWNLMZVKJRSC-UHFFFAOYSA-N 2-hydroxyterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(O)=C1 CDOWNLMZVKJRSC-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 description 1
- RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-UHFFFAOYSA-N 0.000 description 1
- UAIUNKRWKOVEES-UHFFFAOYSA-N 3,3',5,5'-tetramethylbenzidine Chemical group CC1=C(N)C(C)=CC(C=2C=C(C)C(N)=C(C)C=2)=C1 UAIUNKRWKOVEES-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 description 1
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- DFSUKONUQMHUKQ-UHFFFAOYSA-N 3-[2-(2,3-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound OC(=O)C1=CC=CC(C(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)(C(F)(F)F)C(F)(F)F)=C1C(O)=O DFSUKONUQMHUKQ-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 1
- BYHMLZGICSEKIY-UHFFFAOYSA-N 3-amino-2-methylbenzoic acid Chemical compound CC1=C(N)C=CC=C1C(O)=O BYHMLZGICSEKIY-UHFFFAOYSA-N 0.000 description 1
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 description 1
- GIMFLOOKFCUUOQ-UHFFFAOYSA-N 3-amino-4-hydroxy-1,2-dihydropyrimidin-6-one Chemical compound NN1CN=C(O)C=C1O GIMFLOOKFCUUOQ-UHFFFAOYSA-N 0.000 description 1
- WXZMGZRGVJLUNP-UHFFFAOYSA-N 3-amino-4-sulfanyl-1,2-dihydropyrimidine-6-thione Chemical compound NN1CNC(=S)C=C1S WXZMGZRGVJLUNP-UHFFFAOYSA-N 0.000 description 1
- MOVCPRNIWIPGGU-UHFFFAOYSA-N 3-amino-5-[(3-amino-5-carboxyphenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC(N)=CC(CC=2C=C(C=C(N)C=2)C(O)=O)=C1 MOVCPRNIWIPGGU-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- KFFUEVDMVNIOHA-UHFFFAOYSA-N 3-aminobenzenethiol Chemical compound NC1=CC=CC(S)=C1 KFFUEVDMVNIOHA-UHFFFAOYSA-N 0.000 description 1
- QMIJLOSXZVDDAT-UHFFFAOYSA-N 3-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=CC(N)=CC(O)=C21 QMIJLOSXZVDDAT-UHFFFAOYSA-N 0.000 description 1
- YIPRQTYMJYGRER-UHFFFAOYSA-N 3-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=CC(N)=CC(C(O)=O)=C21 YIPRQTYMJYGRER-UHFFFAOYSA-N 0.000 description 1
- RRGZIHVGADOGME-UHFFFAOYSA-N 3-aminonaphthalene-1-thiol Chemical compound C1=CC=CC2=CC(N)=CC(S)=C21 RRGZIHVGADOGME-UHFFFAOYSA-N 0.000 description 1
- AUSYVGSRIHOEPI-UHFFFAOYSA-N 3-aminonaphthalene-2-thiol Chemical compound C1=CC=C2C=C(S)C(N)=CC2=C1 AUSYVGSRIHOEPI-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- RSFDFESMVAIVKO-UHFFFAOYSA-N 3-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S)=C1 RSFDFESMVAIVKO-UHFFFAOYSA-N 0.000 description 1
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- JTWYIRAWVVAUBZ-UHFFFAOYSA-N 4-(4-amino-2,3-dimethylphenyl)-2,3-dimethylaniline Chemical group C1=C(N)C(C)=C(C)C(C=2C(=C(C)C(N)=CC=2)C)=C1 JTWYIRAWVVAUBZ-UHFFFAOYSA-N 0.000 description 1
- GPQSJXRIHLUAKX-UHFFFAOYSA-N 4-(4-amino-2-ethylphenyl)-3-ethylaniline Chemical group CCC1=CC(N)=CC=C1C1=CC=C(N)C=C1CC GPQSJXRIHLUAKX-UHFFFAOYSA-N 0.000 description 1
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
- VLZIZQRHZJOXDM-UHFFFAOYSA-N 4-(4-amino-3-ethylphenyl)-2-ethylaniline Chemical group C1=C(N)C(CC)=CC(C=2C=C(CC)C(N)=CC=2)=C1 VLZIZQRHZJOXDM-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- IJJNNSUCZDJDLP-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 IJJNNSUCZDJDLP-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 1
- JVVGCMZNVXAOOZ-UHFFFAOYSA-N 4-[[(4-carboxyphenyl)-dimethylsilyl]oxy-dimethylsilyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1[Si](C)(C)O[Si](C)(C)C1=CC=C(C(O)=O)C=C1 JVVGCMZNVXAOOZ-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 1
- ABJQKDJOYSQVFX-UHFFFAOYSA-N 4-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=C1 ABJQKDJOYSQVFX-UHFFFAOYSA-N 0.000 description 1
- HZVWUBNSJFILOV-UHFFFAOYSA-N 4-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=CC(O)=CC2=C1 HZVWUBNSJFILOV-UHFFFAOYSA-N 0.000 description 1
- GTCAZWRERBLCFJ-UHFFFAOYSA-N 4-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=C(C(O)=O)C2=C1 GTCAZWRERBLCFJ-UHFFFAOYSA-N 0.000 description 1
- JHENTVXBIZIMMA-UHFFFAOYSA-N 4-aminonaphthalene-1-thiol Chemical compound C1=CC=C2C(N)=CC=C(S)C2=C1 JHENTVXBIZIMMA-UHFFFAOYSA-N 0.000 description 1
- HLYLEARJBJRRTJ-UHFFFAOYSA-N 4-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=CC(C(O)=O)=CC2=C1 HLYLEARJBJRRTJ-UHFFFAOYSA-N 0.000 description 1
- AREXLWHDUHMFQE-UHFFFAOYSA-N 4-aminonaphthalene-2-thiol Chemical compound C1=CC=C2C(N)=CC(S)=CC2=C1 AREXLWHDUHMFQE-UHFFFAOYSA-N 0.000 description 1
- IASBMUIXBJNMDW-UHFFFAOYSA-N 4-aminonicotinic acid Chemical compound NC1=CC=NC=C1C(O)=O IASBMUIXBJNMDW-UHFFFAOYSA-N 0.000 description 1
- YNUVMGHGDJXUHN-UHFFFAOYSA-N 4-aminoquinoline-8-thiol Chemical compound C1=CC=C2C(N)=CC=NC2=C1S YNUVMGHGDJXUHN-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- CCTOEAMRIIXGDJ-UHFFFAOYSA-N 4-hydroxy-2-benzofuran-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)OC2=O CCTOEAMRIIXGDJ-UHFFFAOYSA-N 0.000 description 1
- BCEQKAQCUWUNML-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(O)C(C(O)=O)=C1 BCEQKAQCUWUNML-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- PSAGPCOTGOTBQB-UHFFFAOYSA-N 4-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(O)C2=C1 PSAGPCOTGOTBQB-UHFFFAOYSA-N 0.000 description 1
- NIOAVQYSSKOCQP-UHFFFAOYSA-N 4-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC(O)=C21 NIOAVQYSSKOCQP-UHFFFAOYSA-N 0.000 description 1
- JSBBGWWJLQNXNQ-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 JSBBGWWJLQNXNQ-UHFFFAOYSA-N 0.000 description 1
- LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 1
- VJSGJGHLMKUIFY-UHFFFAOYSA-N 4-sulfanylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(S)C2=C1 VJSGJGHLMKUIFY-UHFFFAOYSA-N 0.000 description 1
- XZCBVCRSAHQOER-UHFFFAOYSA-N 4-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC(S)=C21 XZCBVCRSAHQOER-UHFFFAOYSA-N 0.000 description 1
- JSYUFUJLFRBMEN-UHFFFAOYSA-N 4-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C(C(O)=O)=C1 JSYUFUJLFRBMEN-UHFFFAOYSA-N 0.000 description 1
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-N 0.000 description 1
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 1
- DHFAKJVXVKMUPZ-UHFFFAOYSA-N 5-amino-2-[(4-amino-2-carboxycyclohexyl)methyl]cyclohexane-1-carboxylic acid Chemical compound C(=O)(O)C1CC(CCC1CC1C(CC(CC1)N)C(=O)O)N DHFAKJVXVKMUPZ-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- FSBRKZMSECKELY-UHFFFAOYSA-N 5-aminonaphthalen-2-ol Chemical compound OC1=CC=C2C(N)=CC=CC2=C1 FSBRKZMSECKELY-UHFFFAOYSA-N 0.000 description 1
- FPKNJPIDCMAIDW-UHFFFAOYSA-N 5-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1C(O)=O FPKNJPIDCMAIDW-UHFFFAOYSA-N 0.000 description 1
- WGRZTSLWBZOVFI-UHFFFAOYSA-N 5-aminonaphthalene-1-thiol Chemical compound C1=CC=C2C(N)=CC=CC2=C1S WGRZTSLWBZOVFI-UHFFFAOYSA-N 0.000 description 1
- XVOBQVZYYPJXCK-UHFFFAOYSA-N 5-aminonaphthalene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(N)=CC=CC2=C1 XVOBQVZYYPJXCK-UHFFFAOYSA-N 0.000 description 1
- ZHUYLNSBLAZTRJ-UHFFFAOYSA-N 5-aminonaphthalene-2-thiol Chemical compound SC1=CC=C2C(N)=CC=CC2=C1 ZHUYLNSBLAZTRJ-UHFFFAOYSA-N 0.000 description 1
- YDEUKNRKEYICTH-UHFFFAOYSA-N 5-aminoquinolin-8-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=N1 YDEUKNRKEYICTH-UHFFFAOYSA-N 0.000 description 1
- DDJGBTRFBDNVIW-UHFFFAOYSA-N 5-aminoquinoline-8-thiol Chemical compound C1=CC=C2C(N)=CC=C(S)C2=N1 DDJGBTRFBDNVIW-UHFFFAOYSA-N 0.000 description 1
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 1
- NYYMNZLORMNCKK-UHFFFAOYSA-N 5-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1O NYYMNZLORMNCKK-UHFFFAOYSA-N 0.000 description 1
- SMAMQSIENGBTRV-UHFFFAOYSA-N 5-hydroxynaphthalene-2-carboxylic acid Chemical compound OC1=CC=CC2=CC(C(=O)O)=CC=C21 SMAMQSIENGBTRV-UHFFFAOYSA-N 0.000 description 1
- VTUGNNIWJSWUSP-UHFFFAOYSA-N 5-sulfanylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1S VTUGNNIWJSWUSP-UHFFFAOYSA-N 0.000 description 1
- NQSLRCGJQDKCHO-UHFFFAOYSA-N 5-sulfanylnaphthalene-2-carboxylic acid Chemical compound SC1=CC=CC2=CC(C(=O)O)=CC=C21 NQSLRCGJQDKCHO-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- SERBLGFKBWPCJD-UHFFFAOYSA-N 6-aminonaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(N)=CC=C21 SERBLGFKBWPCJD-UHFFFAOYSA-N 0.000 description 1
- CKSZZOAKPXZMAT-UHFFFAOYSA-N 6-aminonaphthalene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(N)=CC=C21 CKSZZOAKPXZMAT-UHFFFAOYSA-N 0.000 description 1
- OTCMXMNFUXNIKQ-UHFFFAOYSA-N 6-aminonaphthalene-1-thiol Chemical compound SC1=CC=CC2=CC(N)=CC=C21 OTCMXMNFUXNIKQ-UHFFFAOYSA-N 0.000 description 1
- NZTPZUIIYNYZKT-UHFFFAOYSA-N 6-aminonaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(N)=CC=C21 NZTPZUIIYNYZKT-UHFFFAOYSA-N 0.000 description 1
- RMSBBNHNSZBDOJ-UHFFFAOYSA-N 6-aminonaphthalene-2-thiol Chemical compound C1=C(S)C=CC2=CC(N)=CC=C21 RMSBBNHNSZBDOJ-UHFFFAOYSA-N 0.000 description 1
- ZCIFWRHIEBXBOY-UHFFFAOYSA-N 6-aminonicotinic acid Chemical compound NC1=CC=C(C(O)=O)C=N1 ZCIFWRHIEBXBOY-UHFFFAOYSA-N 0.000 description 1
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
- WSUYONLKFXZZRV-UHFFFAOYSA-N 7-aminonaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(N)=CC=C21 WSUYONLKFXZZRV-UHFFFAOYSA-N 0.000 description 1
- BFBAHPDPLUEECU-UHFFFAOYSA-N 7-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(N)=CC=C21 BFBAHPDPLUEECU-UHFFFAOYSA-N 0.000 description 1
- NSLJDNHNUHPTRB-UHFFFAOYSA-N 7-aminonaphthalene-1-thiol Chemical compound C1=CC=C(S)C2=CC(N)=CC=C21 NSLJDNHNUHPTRB-UHFFFAOYSA-N 0.000 description 1
- NBPYPKQPLKDTKB-UHFFFAOYSA-N 7-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(N)=CC=C21 NBPYPKQPLKDTKB-UHFFFAOYSA-N 0.000 description 1
- RYFKPYQPRJODAP-UHFFFAOYSA-N 7-aminonaphthalene-2-thiol Chemical compound C1=CC(S)=CC2=CC(N)=CC=C21 RYFKPYQPRJODAP-UHFFFAOYSA-N 0.000 description 1
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 1
- OXTCGCGDPOLJDV-UHFFFAOYSA-N 8-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(N)=CC=CC2=C1 OXTCGCGDPOLJDV-UHFFFAOYSA-N 0.000 description 1
- WADVNNXCMDTMFG-UHFFFAOYSA-N 8-aminonaphthalene-1-thiol Chemical compound C1=CC(S)=C2C(N)=CC=CC2=C1 WADVNNXCMDTMFG-UHFFFAOYSA-N 0.000 description 1
- PBWULNOSRHQTHZ-UHFFFAOYSA-N 8-aminonaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(N)=CC=CC2=C1 PBWULNOSRHQTHZ-UHFFFAOYSA-N 0.000 description 1
- ZBJJIISFJKHEBB-UHFFFAOYSA-N 8-aminonaphthalene-2-thiol Chemical compound C1=C(S)C=C2C(N)=CC=CC2=C1 ZBJJIISFJKHEBB-UHFFFAOYSA-N 0.000 description 1
- CUIJVFOKZZPKKO-UHFFFAOYSA-N 8-sulfanylnaphthalene-1-carboxylic acid Chemical compound C1=CC(S)=C2C(C(=O)O)=CC=CC2=C1 CUIJVFOKZZPKKO-UHFFFAOYSA-N 0.000 description 1
- PRRFQAVIPFFRRL-UHFFFAOYSA-N 8-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C(S)C2=CC(C(=O)O)=CC=C21 PRRFQAVIPFFRRL-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BZUNJUAMQZRJIP-UHFFFAOYSA-N CPDA Natural products OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 description 1
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 101710189714 Major cell-binding factor Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 102100030000 Recombining binding protein suppressor of hairless Human genes 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JZKNMIIVCWHHGX-UHFFFAOYSA-N adamantane-1,2,2,3-tetracarboxylic acid Chemical compound C1C(C2)CC3CC1(C(=O)O)C(C(O)=O)(C(O)=O)C2(C(O)=O)C3 JZKNMIIVCWHHGX-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical group 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- BKDVBBSUAGJUBA-UHFFFAOYSA-N bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid Chemical compound C1=CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O BKDVBBSUAGJUBA-UHFFFAOYSA-N 0.000 description 1
- ZMCUDHNSHCRDBT-UHFFFAOYSA-M caesium bicarbonate Chemical compound [Cs+].OC([O-])=O ZMCUDHNSHCRDBT-UHFFFAOYSA-M 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid Chemical compound OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- QHGJSLXSVXVKHZ-UHFFFAOYSA-N dilithium;dioxido(dioxo)manganese Chemical compound [Li+].[Li+].[O-][Mn]([O-])(=O)=O QHGJSLXSVXVKHZ-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910021385 hard carbon Inorganic materials 0.000 description 1
- KRHJJLGAWDUWOM-UHFFFAOYSA-N hept-2-ene-1,1,1,2-tetracarboxylic acid Chemical compound C(C(=CCCCC)C(=O)O)(C(=O)O)(C(=O)O)C(=O)O KRHJJLGAWDUWOM-UHFFFAOYSA-N 0.000 description 1
- UJILXQCBVWMDMC-UHFFFAOYSA-N heptane-1,1,1,2-tetracarboxylic acid Chemical compound CCCCCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O UJILXQCBVWMDMC-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- KEDRKJFXBSLXSI-UHFFFAOYSA-M hydron;rubidium(1+);carbonate Chemical compound [Rb+].OC([O-])=O KEDRKJFXBSLXSI-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000003273 ketjen black Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 1
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- GISJHCLTIVIGLX-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methoxy]pyridin-2-yl]-2-(2,6-difluorophenyl)acetamide Chemical compound FC1=CC=CC(F)=C1CC(=O)NC1=CC(OCC=2C=CC(Cl)=CC=2)=CC=N1 GISJHCLTIVIGLX-UHFFFAOYSA-N 0.000 description 1
- 239000005543 nano-size silicon particle Substances 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- 229910021382 natural graphite Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- FYCDKSZYLQMRAV-UHFFFAOYSA-N octane-1,1,1,2-tetracarboxylic acid Chemical compound CCCCCCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O FYCDKSZYLQMRAV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- VLYFRFHWUBBLRR-UHFFFAOYSA-L potassium;sodium;carbonate Chemical compound [Na+].[K+].[O-]C([O-])=O VLYFRFHWUBBLRR-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1017—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)amine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
- C08K3/105—Compounds containing metals of Groups 1 to 3 or of Groups 11 to 13 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/02—Ingredients treated with inorganic substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
- H01B13/0026—Apparatus for manufacturing conducting or semi-conducting layers, e.g. deposition of metal
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B5/00—Non-insulated conductors or conductive bodies characterised by their form
- H01B5/14—Non-insulated conductors or conductive bodies characterised by their form comprising conductive layers or films on insulating-supports
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/26—Electrodes characterised by their structure, e.g. multi-layered, porosity or surface features
- H01G11/28—Electrodes characterised by their structure, e.g. multi-layered, porosity or surface features arranged or disposed on a current collector; Layers or phases between electrodes and current collectors, e.g. adhesives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/32—Carbon-based
- H01G11/38—Carbon pastes or blends; Binders or additives therein
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
- H01M4/139—Processes of manufacture
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/38—Selection of substances as active materials, active masses, active liquids of elements or alloys
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
- H01M4/621—Binders
- H01M4/622—Binders being polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0818—Alkali metal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2203—Oxides; Hydroxides of metals of lithium
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/362—Composites
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/38—Selection of substances as active materials, active masses, active liquids of elements or alloys
- H01M4/386—Silicon or alloys based on silicon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01M4/583—Carbonaceous material, e.g. graphite-intercalation compounds or CFx
- H01M4/587—Carbonaceous material, e.g. graphite-intercalation compounds or CFx for inserting or intercalating light metals
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
-
- 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
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/60—Other road transportation technologies with climate change mitigation effect
- Y02T10/70—Energy storage systems for electromobility, e.g. batteries
Definitions
- the present invention relates to a resin composition, a laminate and a method of manufacturing the same, an electrode, a secondary battery, and an electric double layer capacitor.
- Lithium-ion batteries as rechargeable high-capacity batteries, have made it possible to enhance the functionality of electronic devices and to operate for a long time. Furthermore, lithium ion batteries are mounted in automobiles and the like, and are considered as promising batteries for hybrid vehicles and electric vehicles.
- a lithium ion battery widely used at present is formed by applying a slurry containing an active material such as lithium cobalt oxide and a binder such as polyvinylidene fluoride (PVDF) on an aluminum foil as a positive electrode.
- PVDF polyvinylidene fluoride
- a negative electrode what has formed by apply
- polyimide resins having a higher strength and a higher elastic modulus as a binder for the negative electrode (see, for example, Patent Document 2).
- polyimide resins generally dissolve only in organic solvents such as N-methyl pyrrolidone and N, N'-dimethylacetamide, and thus have a problem of high environmental impact. For this reason, the resin is mixed with a solvent of water system, and examination using it as a water system binder is advanced.
- an aqueous solution of a polyimide resin an aqueous solution of a polyimide precursor to which a water-soluble organic amine or an imidazole compound is added (for example, see Patent Documents 3 to 4), and a hydroxyl group, carboxyl group or sulfonic acid group in the side chain
- transduced, the hydroxide of an alkali metal, etc. is known (for example, refer patent document 5 and non-patent document 1).
- the aqueous solution of the polyimide precursor as described in Patent Documents 3 to 4 has a problem that the polymer main chain is hydrolyzed and the aqueous solution is deteriorated.
- the aqueous solution of polyimide resin as described in Patent Document 5 and Non-patent Document 1 has a problem that the long-term stability when it is an aqueous solution is insufficient because the solubility of the resin in water is low. there were.
- the interaction between the ionized side chains and the filler is small, and when this aqueous solution is used as a slurry, there is a problem that sufficient filler dispersibility and binding ability as a binder can not be obtained.
- the present invention is a resin containing at least one of (a) polyimide, polyamideimide and polybenzoxazole, which has at least one acidic functional group of phenolic hydroxyl group, carboxyl group and sulfonic acid group in the side chain. It is a resin composition containing a resin having a concentration of the acid functional group of 3.4 mol / kg or more and (b) a basic compound.
- the present invention it is possible to obtain a resin composition having high strength and high elastic modulus, high long-term stability of an aqueous solution, good filler dispersibility, and good binding property as a binder.
- the resin composition according to the embodiment of the present invention is a resin containing at least one of (a) polyimide, polyamideimide and polybenzoxazole, and a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group in the side chain And at least one acidic functional group, wherein the concentration of the acidic functional group is 3.4 mol / kg or more, and (b) a resin composition containing a basic compound.
- a resin containing at least one of polyimide, polyamideimide and polybenzoxazole has at least one acidic functional group of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group in a side chain.
- the resin of (a) is excellent in the solubility to water by having an acidic functional group in a side chain.
- the resin of (a) contains 50 mol% or more of the repeating unit structure containing at least one of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group in the side chain, thereby having solubility in water. It is preferable for further improvement.
- content of the said repeating unit structure in resin of (a) 70 mol% or more is more preferable, and 90 mol% or more is further more preferable.
- the polyimide is, for example, a polymer obtained by reacting a diamine and a tetracarboxylic acid or a derivative thereof. It is preferable that the diamine residue in the polyimide has at least one of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group.
- Polyamideimide is, for example, a polymer obtained by reacting diamine with tricarboxylic acid or its derivative.
- the diamine residue in the polyamideimide preferably has at least one of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group.
- Polybenzoxazole is, for example, a polymer obtained by reacting a diamine having a hydroxyl group with a dicarboxylic acid or a derivative thereof. It is preferable that the dicarboxylic acid residue in the polybenzoxazole have at least one of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group.
- diamines include bis (3-amino-4-hydroxyphenyl) hexafluoropropane, bis (3-amino-4-hydroxyphenyl) sulfone, bis (3-amino-4-hydroxyphenyl) propane, bis (3-amino-4-hydroxyphenyl) methylene, bis (3-amino-4-hydroxyphenyl) ether, bis (3-amino-4-hydroxy) biphenyl, bis (3-amino-4-hydroxyphenyl) fluorene, Bis (4-amino-3-hydroxyphenyl) hexafluoropropane, bis (4-amino-3-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) propane, bis (4-amino-3-hydroxy) Phenyl) methylene, bis (4-amino-3-hydroxy) Diamines having a hydroxyl group such as nyl) ether, bis (4-amino-3-hydroxy) biphenyl,
- diamine other diamine
- diamine other diamine
- Preferred specific examples of other diamines include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 3,3'-Diaminodiphenylmethane, 3,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 3,4'-diaminodiphenyl sulfide, 4,4'-diamino Diphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 1,4-bis (4-aminophenoxy) benzene, m-phenylenediamine, p-phenylenediamine
- the diamine having a hydroxyl group shown above is preferably used.
- Preferred specific examples of the tetracarboxylic acid or its derivative include pyromellitic acid, 3,3 ′, 4,4′-biphenyl tetracarboxylic acid, 2,3,3 ′, 4′-biphenyl tetracarboxylic acid, 2,2 ', 3,3'-biphenyltetracarboxylic acid, 3,3', 4,4'-benzophenonetetracarboxylic acid, 2,2 ', 3,3'-benzophenonetetracarboxylic acid, 2,2-bis (3, 4-dicarboxyphenyl) hexafluoropropane, 2,2-bis (2,3-dicarboxyphenyl) hexafluoropropane, 1,1-bis (3,4-dicarboxyphenyl) ethane, 1,1-bis 2,3-Dicarboxyphenyl) ethane, bis (3,4-dicarboxyphenyl) methane, bis (2,
- tricarboxylic acid or its derivative include trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, biphenyl tricarboxylic acid, and anhydrides of these tricarboxylic acids.
- dicarboxylic acid or its derivative examples include 3,5-dicarboxyphenol, 2,4-dicarboxyphenol, and dicarboxylic acids having a hydroxyl group such as 2,5-dicarboxyphenol, and 3,5-dicarboxylate.
- dicarboxylic acids having a sulfonic acid group such as carboxybenzenesulfonic acid, 2,4-dicarboxybenzenesulfonic acid, and 2,5-dicarboxybenzenesulfonic acid.
- dicarboxylic acid other than dicarboxylic acid having at least one of phenolic hydroxyl group, carboxyl group and sulfonic acid group (other dicarboxylic acid) is used as a copolymerization component within the range that the long-term stability of aqueous solution is not impaired. good.
- dicarboxylic acids include terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, diphenyl sulfone dicarboxylic acid, diphenyl methane dicarboxylic acid, biphenyl dicarboxylic acid, 2,2′-bis (carboxyphenyl) propane, 2,2 ′. And -bis (carboxyphenyl) hexafluoropropane and the like.
- the resin (a) may be used as a mixture with resins (other resins) other than polyimide, polyamideimide and polybenzoxazole.
- resins other resins
- Preferred specific examples of the other resin include acrylic resin, methacrylic resin, vinyl resin, phenol resin and cellulose resin.
- Particularly preferred examples include polyvinyl alcohol, polyvinyl pyrrolidone and carboxymethyl cellulose.
- the resin of (a) is preferably contained 80% by mass or more of the whole resin, more preferably 85% by mol or more, still more preferably 90 mols. % Or more, most preferably 95% by mol or more.
- the concentration of the acidic functional group in the resin (a) is 3.4 mol / kg or more, preferably 3.5 mol / kg or more, more preferably 4.0 mol / kg or more, and most preferably Is 4.3 mol / kg or more.
- the concentration of the acidic functional group in the resin (a) is 3.4 mol / kg or more, preferably 3.5 mol / kg or more, more preferably 4.0 mol / kg or more, and most preferably Is 4.3 mol / kg or more.
- the concentration of the acidic functional group as referred to herein is the number of moles of the acidic functional group contained in 1 kg of the resin of (a), and is calculated as follows. Let A (piece) be the number of acidic functional groups in the repeating unit of the resin of (a), and B be the molecular weight of the repeating unit.
- the functional group concentration is calculated by A / B ⁇ 1000.
- the resin of (a) is a copolymer having a plurality of repeating units
- the sum of the product of the functional group concentration and the molar ratio of each repeating unit is the functional group concentration of the resin of (a) Do.
- the functional group concentration Is 1.4 / 498 ⁇ 1000 2.81.
- the resin of (a) preferably contains a structure represented by the following general formula (1) as a repeating unit.
- R 1 represents a divalent organic group having 2 to 50 carbon atoms, and contains at least one of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group.
- R 2 represents a trivalent or tetravalent organic group having 2 to 50 carbon atoms.
- the resin containing the structure represented by the general formula (1) as a repeating unit is, for example, a diamine containing at least one of phenolic hydroxyl group, carboxyl group and sulfonic acid group in the structure, and a tetracarboxylic acid or a derivative thereof Can be obtained by reacting
- the resin containing the structure represented by (1) as a repeating unit is preferably contained in an amount of 60% by mole or more, more preferably 80% by mole or more, still more preferably 90% by mole or more of the entire resin of (a) Most preferably at least 95 mol%.
- the content of the structural unit represented by the general formula (1) in the resin can be estimated by the following method.
- One is infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), thermogravimetry-mass spectrometry (TG-MS), time-of-flight secondary ion mass spectrometry (TOF-SIMS), etc. Is a method to analyze.
- Another method is a method in which the resin is decomposed into each component and then analyzed by gas chromatography (GC), high performance liquid chromatography (HPLC), mass spectrometry (MS), FT-IR, NMR and the like.
- Yet another method is a method in which the resin is ashed at high temperature and then analyzed by elemental analysis or the like.
- the resin is decomposed into each component and then analyzed by combining high performance liquid chromatography (HPLC) and mass spectrometry (MS).
- HPLC high performance liquid chromatography
- MS mass spectrometry
- R 1 represents a diamine residue containing at least one of phenolic hydroxyl group, carboxyl group and sulfonic acid group in the structure. Specific examples of preferred diamines giving the above-mentioned diamine residue are as described above.
- 20 mol% or more of the structure having R 1 having an aromatic skeleton preferable. That is, it is preferable that 20 mol% or more of R 1 in the resin of (a) is an aromatic diamine residue. More preferably, it is 50 mol% or more, still more preferably 70 mol% or more, and most preferably 90 mol% or more.
- R 1 is more preferably at least one of the following general formulas (2) and (3).
- R 15 represents a halogen atom or a monovalent organic group having 1 to 8 carbon atoms.
- s represents an integer of 0 to 3.
- t represents an integer of 1 or 2.
- R 16 and R 17 each independently represent a halogen atom or a monovalent organic group having 1 to 8 carbon atoms.
- u and v each independently represent an integer of 0 to 3.
- w and x each independently represent an integer of 1 or 2;
- R 18 is a single bond, O, S, NH, SO 2 , CO or a divalent organic group having 1 to 3 carbon atoms.
- Preferred specific examples of the divalent organic group having 1 to 3 carbon atoms include saturated hydrocarbon groups having 1 to 3 carbon atoms.
- s is from the viewpoint of further enhancing the interaction between the resin and the filler and further improving the dispersibility of the filler in the resin composition and the binding property as a binder. It is preferably 0.
- u and v is preferably 0.
- the residue of the other diamine described above may be included as long as the long-term stability of the aqueous solution is not impaired.
- the preferred content of the other diamine residue is 40 mol% or less of R 1 in the resin of (a), more preferably 30 mol% or less, and still more preferably 25 mol% or less. Preferably it is 10 mol% or less.
- the composition contains a filler described later, increasing the interaction between the resin and the filler, it improves the dispersibility of the filler in the resin composition, particularly preferably from the viewpoint of improving the chemical resistance of the R 1 1 25 mol% is at least one of the following general formulas (4) and (5).
- R 19 represents a halogen atom or a monovalent organic group having 1 to 8 carbon atoms.
- k represents an integer of 0 to 4; In the case where the resin composition contains a filler described later, k is k from the viewpoint of further enhancing the interaction between the resin and the filler and further improving the dispersibility of the filler in the resin composition and the binding property as a binder. It is preferably 0.
- Each of R 20 and R 21 independently represents a halogen atom or a monovalent organic group having 1 to 8 carbon atoms.
- l and m each independently represent an integer of 0 to 4;
- R 22 is a single bond, O, S, NH, SO 2 , CO or a divalent organic group having 1 to 3 carbon atoms.
- Preferred specific examples of the divalent organic group having 1 to 3 carbon atoms include saturated hydrocarbon groups having 1 to 3 carbon atoms.
- the interaction between the resin and the filler is further enhanced to improve the dispersibility of the filler in the resin composition and the binding property as a binder, l and m is preferably 0.
- diisocyanate compounds in which isocyanate groups are bonded to the structure of diamine residues instead of amino groups, and two hydrogen atoms of amino groups of diamines are substituted with trimethylsilyl groups It is also possible to use tetratrimethylsilylated diamines.
- 1 to 10 mol% of R 1 in the resin of (a) may be a diamine residue containing a siloxane bond.
- a specific diamine which gives a diamine residue containing a siloxane bond 1,3-bis (3-aminopropyl) tetramethyl disiloxane etc. are mentioned.
- the composition contains a filler described later, the interaction between the resin and the filler is enhanced, the dispersibility of the filler in the resin composition is improved, and the thickness uniformity of the film produced from the resin composition is improved. It is preferable that 0.1 to 10 mol% of R 1 be the following general formula (6).
- R 2 represents a tetracarboxylic acid residue (hereinafter referred to as “acid residue”).
- acid residue a tetracarboxylic acid residue
- Examples of preferred tetracarboxylic acids or derivatives thereof which give acid residues are as described above.
- hydrogen atoms of carboxylic acid residues based on the tetracarboxylic acids exemplified above may be substituted by 1 to 4 hydroxyl groups, amino groups, sulfonic acid groups, sulfonic acid amide groups or sulfonic acid ester groups. It is also good.
- the acid residue is preferably at least one selected from the following structures. That is, it is preferable that R 2 is at least one selected from the following structures. Among these, those of aliphatic structure are more preferable.
- R 3 and R 4 each independently represent a halogen atom or an organic group having 1 to 6 carbon atoms.
- R 5 to R 14 each independently represent a hydrogen atom, a halogen atom or an organic group having 1 to 6 carbon atoms.
- a 1 is an integer of 0 to 2;
- a 2 is an integer of 0 to 4;
- Each of a 3 and a 4 is independently an integer of 0 to 4, and a 3 + a 4 ⁇ 5.
- a 6 is an integer of 0 to 6;
- Each of a 5 and a 7 is independently an integer of 0 to 2.
- R 3 and R 4 include a chlorine atom, a fluorine atom, a saturated hydrocarbon group having 1 to 4 carbon atoms, a cyclic saturated hydrocarbon group having 4 to 6 carbon atoms, and a trifluoromethyl group.
- R 5 to R 14 include a hydrogen atom, a chlorine atom, a fluorine atom, a saturated hydrocarbon group having 1 to 4 carbon atoms, a cyclic saturated hydrocarbon group having 4 to 6 carbon atoms, a trifluoromethyl group, etc. It can be mentioned.
- R 5 -R 14 is more preferably a hydrogen atom.
- a 1 and a 2 are preferably 0, a 3 + a 4 ⁇ 2 and a 6 is preferably 0 to 2, more preferably 0 preferably, it is preferred that a 5 and a 7 is 0 to 1, and more preferably 0.
- the most preferable acid residue for obtaining the above effect is the following structure.
- carboxyl compounds having a siloxane bond such as 2,3-tetramethyldisiloxane and 1,3-bisphthalic acid-1,1,3,3-tetramethyldisiloxane.
- the terminal skeleton of the resin containing the structure represented by the general formula (1) as a repeating unit is represented by the following general formulas (7), (8) and (9) It is preferable to include at least one selected from the following structures.
- Each of R 25 , R 26 and R 27 independently represents a monovalent organic group having 4 to 30 carbon atoms, and contains at least one of a phenolic hydroxyl group, a carboxyl group and a sulfonic acid group.
- These structures can be introduced by capping the end of the resin with a capping agent such as an acid anhydride, a monocarboxylic acid, and a monoamine compound.
- a capping agent such as an acid anhydride, a monocarboxylic acid, and a monoamine compound.
- 25 represents a residue of an acid anhydride.
- the acid anhydride include 3-hydroxyphthalic acid anhydride and the like.
- R 26 represents a residue of monocarboxylic acid.
- monocarboxylic acid include 2-carboxyphenol, 3-carboxyphenol, 4-carboxyphenol, 2-carboxythiophenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-8-carboxynaphthalene 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-hydroxy-4-carboxynaphthalene, 1-hydroxy-3-carboxynaphthalene, 1-hydroxy- 2-Carboxynaphthalene, 1-mercapto-8-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 1- Mercapto-4-carboxynaphthalene, 1-mercapto-3-carboxynaphthalene, 1-mer
- R 27 represents a monoamine residue.
- monoamines are 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 5-amino-8-hydroxyquinoline, 4-amino-8-hydroxyquinoline 1-hydroxy-8-aminonaphthalene, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 1-hydroxy- 3-aminonaphthalene, 1-hydroxy-2-aminonaphthalene, 1-amino-7-hydroxynaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 2-hydroxy-4-aminonaphthalene, -Hydroxy-3-aminonaphthalene, 1-amino-2-hydroxynaphthalene, 1-carboxy-8
- terminal anhydrides such as an acid anhydride, a monocarboxylic acid and a monoamine compound can be used alone or in combination of two or more. Moreover, you may use terminal blocking agents other than these together.
- the content of the above-mentioned end capping agent in the resin (a) is preferably in the range of 0.1 to 60 mol% of the molar number of the component monomers constituting the carboxylic acid residue and the amine residue, and 5 to 50 mol% is more preferable. By setting it as such a range, the viscosity of the solution at the time of apply
- the weight average molecular weight of the resin (a) is preferably 10,000 or more and 150,000 or less.
- the weight average molecular weight is a value measured by GPC (gel permeation chromatography) and determined in terms of polystyrene. The measurement conditions of GPC are described below.
- the preparation ratio (molar ratio) of diamine to acid is preferably 100: 50 to 150.
- the solvent used for the polycondensation reaction is not particularly limited as long as the produced resin dissolves, but N-methyl-2-pyrrolidone, N-methylcaprolactam, N, N-dimethylacetamide, Aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, ⁇ -butyrolactone and dimethylimidazoline
- Phenolic solvents such as phenol, m-cresol, chlorophenol and nitrophenol, polyphosphoric acid, phosphoric acid and phosphoric pentoxide Phosphorous solvents or the like to which is added can be preferably used.
- a polyimide polymer is obtained by reacting an acid anhydride or dicarboxylic acid diester with a diamine or diisocyanate in these solvents at a temperature of 150 ° C. or higher.
- bases such as a triethylamine and a pyridine, can be added as a catalyst for reaction promotion. Thereafter, the polymer is poured into water or the like to precipitate a resin, which is then dried to obtain a polymer as a solid.
- the resin composition according to the embodiment of the present invention comprises (b) a basic compound, and thereby the phenolic hydroxyl group, carboxyl group or sulfonic acid group contained in the resin of (a) and (b) the basic compound Form a salt, and the solubility and dispersion stability in water of the resin composition are improved.
- Examples of the basic compound include hydroxides and carbonates of alkali metals and alkaline earth metals, and organic amines.
- a compound containing at least one element selected from alkali metals is preferable.
- alkali metal hydroxides examples include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide and cesium hydroxide. Two or more of these may be contained. Lithium hydroxide, sodium hydroxide and potassium hydroxide are preferable from the viewpoint of improving the water solubility and dispersion stability of the resin composition.
- alkali metal carbonates include lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, potassium hydrogen carbonate, rubidium hydrogen carbonate, cesium carbonate, cesium hydrogen carbonate, potassium potassium carbonate and the like. It can. Two or more of these may be contained. From the viewpoint of water solubility and dispersion stability of the resin composition, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate and sodium potassium carbonate are preferable, and sodium carbonate and sodium hydrogencarbonate are more preferable.
- Organic amines include aliphatic tertiary amines such as trimethylamine, triethylamine, triisopropylamine, tributylamine, triethanolamine, N-methylethanolamine and the like, and aromatics such as pyridine, N, N-dimethylaminopyridine and lutidine Examples thereof include amines, quaternary ammonium salts such as tetramethyl ammonium hydroxide and tetraethyl ammonium hydroxide. Two or more of these may be used.
- sodium carbonate and sodium hydroxide are particularly preferable as the (b) basic compound.
- the content of the (b) basic compound in the resin composition is preferably 20 mol% or more, and 50 mol or more in that the resin can be sufficiently dissolved with respect to 100 mol% of the acidic functional group in the resin of (a). % Or more is more preferable. In addition, 450 mol% or less is preferable, 400 mol% or less is more preferable, 300 mol% or less is preferable, and 250 mol% or less is most preferable in that it is possible to prevent decomposition of resin and generation of cracks when forming a coating film. .
- the resin composition according to the embodiment of the present invention preferably has a solid content concentration of 15% by mass and a pH of 4 to 12 when dissolved in water.
- the preferable range of the pH of the resin composition is 5 or more, and 10 or less.
- the pH value is a resin containing at least one of (a) polyimide, polyamideimide and polybenzoxazole, and the side chain contains at least one acidic functional group of phenolic hydroxyl group, carboxyl group and sulfonic acid group.
- a resin composition containing a basic compound and having a concentration of not less than 3.4 mol / kg of the acid functional group is dissolved in water at a concentration of 15% by mass, or a member of a battery
- A a resin containing at least one of polyimide, polyamideimide and polybenzoxazole completely extracted from the above, wherein at least one acidic functional group among phenolic hydroxyl group, carboxyl group and sulfonic acid group is included in the side chain
- a resin composition containing (b) a basic compound, and a resin having a concentration of the acid functional group of 3.4 mol / kg or more A value which is dissolved in water in degrees 15 mass%.
- the resin composition according to the embodiment of the present invention contains (c) water as a solvent.
- (c) water in the solvent preferably accounts for 80% by mass or more of the solvent contained in the resin composition. More preferably, it is 90 mass% or more, Most preferably, it is 99 mass% or more.
- the resin composition according to the embodiment of the present invention preferably contains (c) 50 to 1,000,000 parts by mass of water with respect to 100 parts by mass of the resin of (a).
- a the amount of water (c) is preferably 100,000 parts by mass or less, and more preferably 3,000 parts by mass or less from the viewpoint of suppressing decomposition.
- the viscosity of the resin composition according to the embodiment of the present invention is preferably in the range of 1 mPa ⁇ s to 100 Pa ⁇ s at 25 ° C. from the viewpoint of workability.
- the resin composition according to the embodiment of the present invention preferably has a pH of 4 to 12. Outside this range, the dispersibility of the filler when the resin composition contains the filler described later is deteriorated, and the thickness uniformity, strength and chemical resistance of the coating film produced from the resin composition are lowered. From the viewpoint of further improving the above-mentioned properties, the preferable range of the pH of the resin composition is 5 or more, and 10 or less.
- the pH in the present invention is a value measured using a pH meter (LAQUA F-71, manufactured by Horiba, Ltd.).
- the calibration of pH is performed using the following five types of standard solutions (pH 2, 4, 7, 9, 12) as defined in JIS Z 8802 (2011) "pH measuring method".
- the resin composition according to the embodiment of the present invention may contain a surfactant or the like from the viewpoint of further improving the coatability.
- an organic solvent such as a lower alcohol such as ethanol or isopropyl alcohol, or a polyhydric alcohol such as ethylene glycol or propylene glycol may be contained. 50 mass% or less of the whole resin composition is preferable, and, as for content of the organic solvent in a resin composition, 10 mass% or less is more preferable.
- the method for preparing the resin composition according to the embodiment of the present invention is safe to dissolve the resin powder little by little after dissolving a predetermined amount of the basic compound in water. It is preferable from the viewpoint of When the neutralization reaction is slow, heating may be performed with a water bath or an oil bath at about 30 to 110 ° C., or ultrasonic treatment may be performed. After dissolution, water may be further added or concentrated to adjust to a predetermined viscosity.
- the resin composition according to the embodiment of the present invention may contain (d) a filler.
- the resin composition contains (d) a filler, the mechanical strength and heat resistance of the film produced from the resin composition are improved.
- the resin composition it is also possible to use the resin composition as an electronic material or an optical material by using conductive particles, a high refractive filler or a low refractive filler as the (d) filler.
- the resin composition containing a filler may be in the form of a slurry.
- the filler (d) include compounds containing at least one atom of carbon, manganese, aluminum, barium, cobalt, nickel, iron, silicon, titanium, tin, and germanium. These compounds serve as electrode active materials, strength reinforcing materials, heat conductive materials or high dielectric materials. Therefore, the resin composition according to the embodiment of the present invention contains a filler and can be used as a slurry for functional components such as electronic components, secondary batteries, electric double layer capacitors, etc.
- Examples of the filler for the positive electrode in the secondary battery and the electric double layer capacitor include lithium iron phosphate, lithium cobaltate, lithium nickelate, lithium manganate, activated carbon and carbon nanotubes.
- Examples of the filler for the negative electrode in secondary batteries and electric double layer capacitors include silicon, silicon oxide, silicon carbide, tin, tin oxide, germanium, lithium titanate, hard carbon, soft carbon, activated carbon and carbon nanotubes Be
- a storage battery using silicon, tin, or germanium as an active material has a large volume expansion of the active material at the time of charging, and therefore, it is possible to use a resin with high mechanical strength such as the resin of (a) as a binder It is preferable in order to prevent the micronization of When the filler is lithium titanate, a secondary battery or an electric double layer capacitor excellent in rate characteristics can be obtained.
- the filler for the negative electrode include silicon, silicon oxide, lithium titanate, silicon carbide, a mixture of two or more of them, a mixture of one or more of them and carbon and And a mixture of at least one of one or two or more of them in which the surface of the mixture is carbon-coated.
- These active materials are particularly strong in the binding property with the resin (a), and a secondary battery with a high capacity retention rate and an electric double layer capacitor can be obtained.
- the content of the (d) filler in the resin composition according to the embodiment of the present invention can improve the mechanical strength and heat resistance of the film obtained from the resin composition with respect to 100 parts by mass of the resin of (a) 0.01 mass part or more is preferable, 0.1 mass part or more is more preferable. Moreover, in the point which can maintain the coating film strength of a resin composition, 100,000 mass parts or less are preferable, and 10,000 mass parts or less are more preferable.
- the slurry can be obtained, for example, by adding a filler and, if necessary, other components to a solution or dispersion of a resin in water or a solvent, and uniformly mixing.
- examples of the mixing include methods using a planetary mixer, a rotation and revolution mixer, a three-roll mill, a ball mill, a mechanical stirrer, a thin film swirl mixer, and the like.
- the laminate according to the embodiment of the present invention has a layer formed from the above-mentioned resin composition on at least one side of a substrate.
- This laminate can be obtained, for example, by applying a resin composition to one side or both sides of a substrate and drying it.
- metal foils such as copper foil, aluminum foil, stainless steel foil, a silicon substrate, a glass substrate, a plastic film, etc. are used preferably.
- the coating method include methods using a roll coater, a slit die coater, a bar coater, a comma coater, a spin coater, and the like.
- the drying temperature is preferably 30 ° C. or more, more preferably 50 ° C. or more, in order to completely remove water.
- 500 degrees C or less is preferable, and 200 degrees C or less is more preferable.
- the resin composition according to the embodiment of the present invention may contain a conductive aid such as acetylene black, ketjen black, or carbon nanotube.
- the charge / discharge rate can be improved by containing the conductive aid.
- the content of the conductive additive is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the active material in order to achieve both conductivity and capacity.
- the resin composition according to the embodiment of the present invention may contain a sodium salt of carboxymethylcellulose for viscosity adjustment.
- the content is preferably 50 parts by mass or less with respect to 100 parts by mass of the active material from the viewpoint of having a high capacity retention rate in the secondary battery or the electric double layer capacitor.
- a resin composition or a resin composition containing a filler is applied and dried on at least one surface of a substrate to form a film, thereby forming a laminate.
- the substrate include an insulating substrate, a conductive substrate, and the like, but when used as an electronic device, a conductive substrate or an insulating substrate having a conductive wiring is preferable.
- the electrode of a secondary battery or an electric double layer capacitor is coated with a resin composition containing an electrode active material as a filler on one side or both sides of a current collector such as copper foil, aluminum foil or stainless steel foil and dried.
- the positive electrode and the negative electrode obtained in this manner are stacked in multiple layers via a separator, and put together with an electrolytic solution in an exterior material such as a metal case and sealed to store electricity, such as a secondary battery or an electric double layer capacitor. You can get the device.
- separator examples include microporous films and non-woven fabrics made of materials such as polyolefins such as polyethylene and polypropylene, cellulose, polyphenylene sulfide, aramid, or polyimide.
- carbonate compounds such as propylene carbonate, ethylene carbonate, dimethyl carbonate, ethyl methyl carbonate, vinylene carbonate, acetonitrile, sulfolane, ⁇ -butyrolactone and the like can be used. Two or more of these may be used.
- electrolyte examples include lithium salts such as lithium hexafluorophosphate, lithium borofluoride and lithium perchlorate, and ammonium salts such as tetraethylammonium tetrafluoroborate and triethylmethylammonium tetrafluoroborate.
- lithium salts such as lithium hexafluorophosphate, lithium borofluoride and lithium perchlorate
- ammonium salts such as tetraethylammonium tetrafluoroborate and triethylmethylammonium tetrafluoroborate.
- ⁇ PH measurement of aqueous solution A small amount of aqueous solution 1 to 21 was collected, and the pH of the aqueous solution was measured with a pH meter (LAQUA F-71, manufactured by Horiba, Ltd.). The calibration of pH was carried out using the following five standard solutions (pH 2, 4, 7, 9, 12) as defined in JIS Z 8802 (2011) "pH measuring method".
- aqueous solutions 1 to 21 were visually observed after standing for 1 and 3 months at room temperature and for 1 week and 1 month under refrigeration, respectively, and the stability of the aqueous solution was confirmed. Those in which neither precipitation nor gelation was observed were good, and those in which any change was made described the changes that occurred. Those that were good at room temperature for one month were passed, and those that had any change after one month at room temperature were rejected.
- This slurry was coated on an aluminum foil with a bar coater so that the average thickness of the film after heat treatment was 25 ⁇ m and the width was 10 cm. After coating, it was dried at 50 ° C. for 30 minutes, then heated up to 150 ° C. over 30 minutes, heat-treated at 150 ° C. for 1 hour, and then cooled to 50 ° C. or less. After cooling, the film was visually observed to confirm the presence or absence of cracks. Those with no cracks were considered "good", and those with cracks confirmed as "defects”.
- T2 (T1-25) / 25 * 100 (%) Calculated and defined as ⁇ T2%. Those with variation in the range of -30% to + 30% (except when exactly ⁇ 30%) were passed, and those outside the above range were rejected.
- the thickness is adjusted so that the average value of the film thickness after heat treatment becomes 50 ⁇ m by the same method as described above, and 5 pieces are cut out in a circle with a diameter of 16 mm, 50% by weight ratio of diethyl carbonate and ethylene carbonate
- the solution was immersed in the mixed solution and left at 40.degree. C. for 1 week. After standing, the membrane was removed from the solution, washed with water, dried at 50 ° C. for 1 hour, and then visually observed to confirm the presence or absence of dissolution of the membrane and the presence or absence of cracks. Those in which the dissolution of the film was observed were regarded as “dissolved”, those in which the crack was generated were regarded as “defective”, and those in which neither dissolution nor film of the film were found were regarded as “good”.
- ⁇ Battery characteristic evaluation> (1) Preparation of Negative Electrode Using a slurry with a solid content of 50% prepared in ⁇ Characteristics evaluation of film (dispersion, evaluation of binding)>, using a bar coater on an electrodeposited copper foil, at 150 ° C. The thickness was adjusted and applied so that the film thickness after heat treatment was 25 ⁇ m, and after application, it was dried at 110 ° C. for 30 minutes. After drying, the coated portion was punched into a circular shape having a diameter of 16 mm, and vacuum drying was performed at 150 ° C. for 24 hours to obtain a negative electrode.
- the negative electrode, the separator, and the positive electrode were stacked in order, and 1 mL of MIRET 1 (manufactured by Mitsui Chemicals, Inc.) was injected as an electrolytic solution and sealed to obtain a lithium ion battery.
- MIRET 1 manufactured by Mitsui Chemicals, Inc.
- the lithium ion battery manufactured as described above was charged and discharged. Charging is performed until the battery voltage reaches 4.2 V at a constant current of 6 mA, and after the charging starts at a constant voltage of 4.2 V for a total of 2 hours and 30 minutes, and then rested for 30 minutes. One cycle was to discharge the battery voltage to 2.7 V at a constant current of 6 mA. Thereafter, charge and discharge were repeated 49 times under the same conditions, and charge capacity and discharge capacity of each cycle were measured for a total of 50 cycles. Then, the capacity retention rate was calculated according to the following equation.
- Capacity retention rate (%) (discharge capacity at 50th cycle / discharge capacity at 1st cycle) ⁇ 100 Synthesis Example 1: Synthesis of Resin A In a well-dried four-necked flask, 131.79 g of NMP and 3,3'-dicarboxy-4,4'-methylenebis (cyclohexylamine) (manufactured by Tokyo Chemical Industry Co., Ltd.) In the following, 29.84 g (100 mmol) of CMCHA) were dissolved at room temperature with stirring under a nitrogen atmosphere.
- Synthesis Example 2 Synthesis of Resin B Instead of CMCHA 29.84 g (100 mmol), 20.89 g (70 mmol) of CMCHA and 3,3'-dicarboxy-4,4'-diaminodiphenylmethane (manufactured by Wakayama Seika Kogyo Co., Ltd.), A solid of resin B was obtained in the same manner as in Synthesis Example 1 except that 8.59 g (30 mmol) of trade name "MBAA" was used. The weight average molecular weight of the resin B was 32000.
- Synthesis Example 3 Synthesis of Resin C A solid of Resin C was obtained in the same manner as in Synthesis Example 1 except that 28.63 g (100 mmol) of MBAA was used instead of 29.84 g (100 mmol) of CMCHA. The weight average molecular weight of Resin C was 35,000.
- Synthesis Example 5 Synthesis of Resin E Instead of 30.00 g (100 mmol) of TDA-100, bicyclo [2,2,2] octo-7-ene-2,3,5,6-tetracarboxylic acid dianhydride (A solid of resin E was obtained in the same manner as in Synthesis Example 4 except that 24.82 g (100 mmol) of Tokyo Chemical Industry Co., Ltd. (hereinafter referred to as BOE) was used. The weight average molecular weight of the resin E was 15,000.
- Synthesis Example 6 Synthesis of Resin F Instead of 30.00 g (100 mmol) of TDA-100, 3- (carboxymethyl) -1,2,4-cyclopentane tricarboxylic acid 1,4: 2,3-dianhydride ( A solid of resin F was obtained in the same manner as in Synthesis Example 4 except that 22.42 g (100 mmol) of Tokyo Chemical Industry Co., Ltd. (hereinafter referred to as JPDA) was used. The weight average molecular weight of the resin F was 20000.
- Synthesis Example 7 Synthesis of Resin G Instead of 30.00 g (100 mmol) of TDA-100, 21.81 g (100 mmol) of pyromellitic dianhydride (manufactured by Daicel Industries, Ltd., trade name "PMDA") was used. A solid of resin G was obtained in the same manner as in Synthesis Example 4 except for the above. The weight average molecular weight of the resin G was 28,000.
- Synthesis Example 8 Synthesis of Resin H Instead of TDA-100 30.00 g (100 mmol), 1,2,3,4-cyclopentane tetracarboxylic acid dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd., CPDA) A solid of resin H was obtained in the same manner as in Synthesis Example 4 except that 21.01 g (100 mmol) was used. The weight average molecular weight of the resin H was 16000.
- Synthesis Example 9 Synthesis of Resin I Instead of 30.00 g (100 mmol) of TDA-100, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd., CBDA) 19 A solid of resin I was obtained in the same manner as in Synthesis Example 4 except that .61 g (100 mmol) was used. The weight average molecular weight of Resin I was 25,000.
- Synthesis Example 10 Synthesis of Resin J Instead of 30.00 g (100 mmol) of TDA-100, 1,2,3,4-butanetetracarboxylic acid dianhydride (manufactured by Wako Chemical Co., Ltd., hereinafter, BTA) 19. A solid of resin J was obtained in the same manner as in Synthesis Example 4 except that 81 g (100 mmol) was used. The weight average molecular weight of the resin J was 35,000.
- the washed solid was dried in a ventilated oven at 50 ° C. for 3 days to obtain a solid of resin K.
- the weight average molecular weight of the resin K was 30,000.
- Synthesis Example 12 Synthesis of Resin L Instead of TDA-100 30.00 g (100 mmol), 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), Thereafter, a solid of resin L was obtained in the same manner as in Synthesis Example 4 except that 6FDA) 44.42 (100 mmol) was used. The weight average molecular weight of the resin L was 65,000.
- Synthesis Example 14 Synthesis of Resin N
- 28.63 g (100 mmol) of MBAA was dissolved in 131.79 NMP at room temperature with stirring under a nitrogen atmosphere. Then, while maintaining the temperature of the solution at 10 ° C. or less, add 20.30 (100 mmol) of isophthaloyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd., IPC hereinafter), 15.00 g of NMP, and 1 hour at 10 ° C. or less Then, the polymerization reaction was carried out at 23 ° C. for 6 hours.
- this solution was poured into 3 L of water, and the resulting precipitate was separated by filtration and washed three times with 1.5 L of water.
- the washed solid was dried in a ventilated oven at 50 ° C. for 3 days to obtain a solid of resin N.
- the weight average molecular weight of the resin N was 30,000.
- compositions, molecular weights and functional group concentrations of the resins of Synthesis Examples 1 to 14 are shown in Table 1.
- Synthesis Example 15 Synthesis of Resin O
- 27.20 g (95 mmol) of MBAA in MBA.131.79 g, 0.54 g of paraphenylene diamine (manufactured by Tokyo Chemical Industry Co., Ltd., PDA, hereinafter) (5 mmol) was dissolved at room temperature with stirring under a nitrogen atmosphere. Thereafter, 19.81 g (100 mmol) of BTA and 15.00 g of NMP were added and reacted at 40 ° C. for 2 hours. Then, the polymerization reaction was conducted at 200 ° C. for 6 hours while distilling off water generated during the reaction.
- the polymerization reaction was conducted at 200 ° C. for 6 hours while distilling off water generated during the reaction. After completion of the reaction, the temperature was lowered to room temperature, this solution was poured into 3 L of water, and the obtained precipitate was separated by filtration and washed three times with 1.5 L of water. The washed solid was dried in a ventilated oven at 50 ° C. for 3 days to obtain a solid of resin P.
- the weight average molecular weight of the resin P was 35,000.
- Synthesis Example 17 Synthesis of Resin Q In a well-dried four-necked flask, stirring of 27.20 g (95 mmol) of MBAA, 0.32 g (3 mmol) of PDA, and 0.10 g (1 mmol) of OBEA in 131.79 g of NMP under a nitrogen atmosphere The solution was allowed to dissolve at room temperature. Thereafter, 19.81 g (100 mmol) of BTA and 15.00 g of NMP were added, 1 h at 40 ° C., 0.28 g (2 mmol) of 4ABA were added, and the reaction was further performed at 40 ° C. for 1 h. Then, the polymerization reaction was conducted at 200 ° C.
- the washed solid was dried in a ventilated oven at 50 ° C. for 3 days to obtain a solid of resin Q.
- the weight average molecular weight of the resin Q was 30,000.
- Synthesis Example 18 Synthesis of Resin R 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride instead of 30.00 g (100 mmol) of TDA-100
- a solid of resin R was obtained in the same manner as in Synthesis Example 4 except that 26.42 g (100 mmol) (trade name "EPICLON B-4400" manufactured by DIC Corporation) was used.
- the weight average molecular weight of the resin R was 20000.
- Aqueous solution 1 to 21 As described in Table 1, the resin, the basic compound and water were mixed to prepare an aqueous solution having a solid content concentration of 15% by mass.
- the compositions of the aqueous solutions 1 to 21 and the pH values of the aqueous solutions are shown in Table 2.
- Comparative Example 8 80 parts by mass of the negative electrode active material for lithium ion battery obtained in Synthesis Example 15, 15 parts by mass of polyvinylidene fluoride (manufactured by Kishda Chemical Co., Ltd., hereinafter, PVdF), 5 parts by mass of acetylene black as a conductive additive, and 100 parts by mass of NMP It mixed and disperse
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Electrochemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Fixed Capacitors And Capacitor Manufacturing Machines (AREA)
Abstract
Description
本発明の実施の形態に係る樹脂組成物は、(a)ポリイミド、ポリアミドイミドおよびポリベンゾオキサゾールのうち少なくとも1つを含む樹脂であって、側鎖に、フェノール性水酸基、カルボキシル基およびスルホン酸基のうち少なくとも1つの酸性官能基を有し、該酸性官能基の濃度が3.4モル/kg以上である樹脂と、(b)塩基性化合物を含む樹脂組成物である。
(a)ポリイミド、ポリアミドイミドおよびポリベンゾオキサゾールのうち少なくとも1種を含む樹脂は、フェノール性水酸基、カルボキシル基およびスルホン酸基のうち少なくとも1つの酸性官能基を側鎖に有する。(a)の樹脂は、酸性官能基を側鎖に有することで、水への溶解性に優れる。
一般式(1)中、R1は、構造中にフェノール性水酸基、カルボキシル基およびスルホン酸基のうち少なくとも1つを含むジアミン残基を表す。上記ジアミン残基を与える好ましいジアミンの具体例としては、前述の通りである。
樹脂組成物が後述のフィラーを含む場合に、樹脂とフィラーとの相互作用がより高まって、樹脂組成物内のフィラーの分散性や、バインダーとしての結着性がより向上する観点から、kは0であることが好ましい。
炭素数1~3の2価の有機基の好ましい具体例としては、炭素数1~3の飽和炭化水素基などが挙げられる。
組成物が後述のフィラーを含む場合に、樹脂とフィラーとの相互作用が高まって、樹脂組成物内のフィラーの分散性が向上し、樹脂組成物から作製した膜の厚み均一性が向上する観点からR1の0.1~10モル%が下記一般式(6)であることが好ましい。
樹脂組成物が後述のフィラーを含む場合に、樹脂とフィラーとの相互作用がより高まって、樹脂組成物内のフィラーの分散性や、バインダーとしての結着性がより向上する観点から、R24は水素原子かつ、p=0であることがより好ましく、さらに1<q<4であることがさらに好ましい。
一般式(1)中、R2はテトラカルボン酸残基(以下、「酸残基」という)を表す。酸残基を与える好ましいテトラカルボン酸またはその誘導体の例としては、前述の通りである。
水溶液の安定性、フィラーの分散性の観点で、一般式(1)で表される構造を繰り返し単位として含む樹脂の末端骨格は、下記一般式(7)、(8)および(9)で表される構造から選ばれた少なくとも1つを含むことが好ましい。
1) 機器装置 : Waters 2690
2) カラム: TOSOH CORPORATION, TSK-GEL(d-4000 & d-2500)
3) 溶媒 : NMP
4) 流速 : 0.4mL/min
5) 試料濃度 : 0.05~0.1 wt%
6) 注入量 : 50μL
7) 温度 : 40℃
8) 検出器 : Waters 996
なお、換算に用いるポリスチレンには、Polymer Laboratories社の標準ポリスチレンを用いる。
本発明の実施の形態に係る樹脂組成物は、(b)塩基性化合物を含むことにより、(a)の樹脂に含まれるフェノール性水酸基、カルボキシル基またはスルホン酸基と(b)塩基性化合物とが塩を形成し、樹脂組成物の水に対する溶解性および分散安定性が向上する。
本発明の実施の形態に係る樹脂組成物は固形分濃度15質量%で水に溶解させたときのpHが4~12であることが好ましい。
この範囲を外れると、樹脂組成物が後述のフィラーを含有する際のフィラーの分散性が悪化し、樹脂組成物から作製した塗膜の、厚み均一性、強度および耐薬品性が低下する。上記特性をより向上させる観点から、樹脂組成物のpHの好ましい範囲は5以上であり、また、10以下である。
pHの値については、(a)ポリイミド、ポリアミドイミドおよびポリベンゾオキサゾールのうち少なくとも1種を含む樹脂であって、側鎖に、フェノール性水酸基、カルボキシル基およびスルホン酸基のうち少なくとも1つの酸性官能基を有し、該酸性官能基の濃度が3.4モル/kg以上である樹脂と、(b)塩基性化合物を含む樹脂組成物を濃度15質量%で水に溶解させるか、電池の部材から完全に抽出した(a)ポリイミド、ポリアミドイミドおよびポリベンゾオキサゾールのうち少なくとも1種を含む樹脂であって、側鎖に、フェノール性水酸基、カルボキシル基およびスルホン酸基のうち少なくとも1つの酸性官能基を有し、該酸性官能基の濃度が3.4モル/kg以上である樹脂と、(b)塩基性化合物を含む樹脂組成物を濃度15質量%で水に溶解させた値とする。
本発明の実施の形態に係る樹脂組成物は溶媒として(c)水を含む。水溶液の安定性の観点から、溶媒中の(c)水は、樹脂組成物に含まれる溶媒のうちの80質量%以上を占めることが好ましい。より好ましくは90質量%以上であり、最も好ましくは99質量%以上である。
○pH2標準液(しゅう酸塩)
0.05mol/L 四しゅう酸カリウム水溶液
○pH4標準液(フタル酸塩)
0.05mol/L フタル酸水素カリウム水溶液
○pH7標準液(中性りん酸塩:下記2水溶液の混合液)
0.025mol/L リン酸二水素カリウム水溶液
0.025mol/L リン酸水素二ナトリウム水溶液
○pH9標準液(ほう酸塩)
0.01mol/L 四ホウ酸ナトリウム(ホウ砂)水溶液
○pH12標準液
飽和水酸化カルシウム水溶液。
本発明の実施の形態に係る樹脂組成物は、(d)フィラーを含有していてもよい。樹脂組成物が(d)フィラーを含有することにより、樹脂組成物から作製した膜の機械強度や耐熱性が向上する。さらに、(d)フィラーとして、導電性の粒子や、高屈折フィラーまたは低屈折フィラーを用いることにより、樹脂組成物を電子材料や光学材料に利用することも可能である。(d)フィラーを含有する樹脂組成物は、スラリー状であってもよい。
本発明の実施の形態に係る積層体は、基材の少なくとも片面に、上述の樹脂組成物から製膜された層を有する。この積層体は、例えば、樹脂組成物を基材の片面または両面に塗布し、乾燥させることで得ることができる。
上記「発明を実施するための形態」欄で説明した算出方法にしたがい、(a)の樹脂における繰り返し単位中の酸性官能基の数Aおよび当該繰り返し単位の分子量Bを求めて、官能基濃度(モル/kg)をA/B×1000として算出した。
樹脂A~Nの分子量は、GPC(ゲルパーミエーションクロマトグラフィー)で測定し、ポリスチレン換算で重量平均分子量(Mw)を計算した。GPC測定条件を下記する。
1) 機器装置 : Waters 2690
2) カラム: TOSOH CORPORATION, TSK-GEL(d-4000 & d-2500)
3) 溶媒 : NMP
4) 流速 : 0.4mL/min
5) 試料濃度 : 0.05~0.1 wt%
6) 注入量 : 50μL
7) 温度 : 40℃
8) 検出器 : Waters 996
なお、換算に用いるポリスチレンには、Polymer Laboratories社の標準ポリスチレンを用いた。
水溶液1~21を少量採取し、pHメーター(LAQUA F-71、堀場製作所製)で水溶液のpHを測定した。pHの校正は、JIS Z 8802(2011)「pH測定方法」に定められているうち、下記の5種類の標準液(pH2、4、7、9、12)を用いて行った。
○pH2標準液(しゅう酸塩)
0.05mol/L 四しゅう酸カリウム水溶液
○pH4標準液(フタル酸塩)
0.05mol/L フタル酸水素カリウム水溶液
○pH7標準液(中性りん酸塩:下記2水溶液の混合液)
0.025mol/L リン酸二水素カリウム水溶液
0.025mol/L リン酸水素二ナトリウム水溶液
○pH9標準液(ほう酸塩)
0.01mol/L 四ホウ酸ナトリウム(ホウ砂)水溶液
○pH12標準液
飽和水酸化カルシウム水溶液。
水溶液1~21を、室温で1ヶ月および3ヶ月、ならびに、冷蔵で1週間および1ヶ月、それぞれ放置後、目視観察し、水溶液の安定性を確認した。析出、ゲル化のいずれも認められないものを良、いずれかの変化があったものは起こった変化を記載した。室温1ヶ月放置で良のものを合格、室温1ヶ月放置でいずれかの変化があったものは不合格とした。
フィラーの分散性、バインダーとしての結着性を見るために、フィラーを有する樹脂組成物の膜特性評価を行った。フィラーの分散性、バインダーとしての結着性が悪いと、フィラーの凝集による膜厚の均一性の悪化が起こったり、膜にクラックが発生したりする。
T2=(T1-25)/25*100(%)
で算出し、±T2%と定義した。ばらつきが-30%から+30%の範囲内にあるもの(ただし、ちょうど±30%である場合は除く)を合格、前記範囲外にあるものを不合格とした。
(1)負極の作製
<膜の特性評価(分散性、結着性の評価)>で作製した固形分50%のスラリーを用い、電解銅箔上に、バーコーターを用いて、150℃での熱処理後の膜厚が25μmになるように厚みを調整して塗布し、塗布後、110℃で30分間乾燥した。乾燥後、塗布部を直径16mmの円形に打ち抜き、150℃で、24時間の真空乾燥を行い、負極とした。
充放電特性を測定する上で、HSセル(宝泉(株)製)を用い、リチウムイオン電池の組み立てを窒素雰囲気下でおこなった。セパレータには、ポリエチレン多孔質フィルム(宝泉(株)製)を直径24mmに打ち抜いたものを用いた。正極には、コバルト酸リチウム製の活物質をアルミ箔に焼成したもの(宝泉(株)製)を直径16mmに打ち抜いたものを用いた。負極、セパレータおよび正極を順に重ね、電解液としてMIRET1(三井化学(株)製)1mLを注入した上で封入して、リチウムイオン電池を得た。
容量維持率(%)=(50サイクル目の放電容量/1サイクル目の放電容量)×100
合成例1:樹脂Aの合成
よく乾燥させた四ツ口フラスコの中で、NMP131.79gに3,3’-ジカルボキシ-4,4’-メチレンビス(シクロヘキシルアミン)(東京化成工業(株)製、以下、CMCHA)29.84g(100mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、3,3’,4,4’-ジフェニルエーテルテトラカルボン酸二無水物(東京化成工業(株)製、以下、ODPA)31.02g(100mmol)、NMP15.00gを添加し、40℃で1時間、ついで反応中に発生する水を留去しながら200℃で6時間重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Aの固体を得た。樹脂Aの重量平均分子量は30000であった。
CMCHA29.84g(100mmol)の代わりに、CMCHA20.89g(70mmol)と3,3’-ジカルボキシ-4,4’-ジアミノジフェニルメタン(和歌山精化工業(株)製、商品名「MBAA」)8.59g(30mmol)を用いた以外は合成例1と同様にして樹脂Bの固体を得た。樹脂Bの重量平均分子量は32000であった。
CMCHA29.84g(100mmol)の代わりに、MBAA28.63g(100mmol)を用いた以外は合成例1と同様にして樹脂Cの固体を得た。樹脂Cの重量平均分子量は35000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gにMBAA28.63g(100mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、1,3,3a,4,5,9b-ヘキサヒドロ-5(テトラヒドロ-2,5-ジオキソ-3-フラニル)ナフト[1,2-c]フラン-1,3-ジオン(新日本理化(株)製、商品名「リカシッド TDA-100」)30.00g(100mmol)、NMP15.00gを添加し、40℃で1時間、ついで反応中に発生する水を留去しながら200℃で6時間重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Dの固体を得た。樹脂Dの重量平均分子量は18000であった。
TDA-100 30.00g(100mmol)の代わりに、ビシクロ[2,2,2]オクト-7-エン-2,3,5,6-テトラカルボン酸二無水物(東京化成工業(株)製、以下、BOE)24.82g(100mmol)を用いた以外は合成例4と同様にして樹脂Eの固体を得た。樹脂Eの重量平均分子量は15000であった。
TDA-100 30.00g(100mmol)の代わりに、3-(カルボキシメチル)-1,2,4-シクロペンタントリカルボン酸1,4:2,3-二無水物(東京化成工業(株)製、以下、JPDA)22.42g(100mmol)を用いた以外は合成例4と同様にして樹脂Fの固体を得た。樹脂Fの重量平均分子量は20000であった。
TDA-100 30.00g(100mmol)の代わりに、ピロメリット酸二無水物(ダイセル工業(株)製、商品名「PMDA」)21.81g(100mmol)を用いた以外は合成例4と同様にして樹脂Gの固体を得た。樹脂Gの重量平均分子量は28000であった。
TDA-100 30.00g(100mmol)の代わりに、1,2,3,4-シクロペンタンテトラカルボン酸二無水物(東京化成工業(株)製、以下、CPDA)21.01g(100mmol)を用いた以外は合成例4と同様にして樹脂Hの固体を得た。樹脂Hの重量平均分子量は16000であった。
TDA-100 30.00g(100mmol)の代わりに、1,2,3,4-シクロブタンテトラカルボン酸二無水物(東京化成工業(株)製、以下、CBDA)19.61g(100mmol)を用いた以外は合成例4と同様にして樹脂Iの固体を得た。樹脂Iの重量平均分子量は25000であった。
TDA-100 30.00g(100mmol)の代わりに、1,2,3,4-ブタンテトラカルボン酸二無水物((株)ワコーケミカル製、以下、BTA)19.81g(100mmol)を用いた以外は合成例4と同様にして樹脂Jの固体を得た。樹脂Jの重量平均分子量は35000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gにMBAA26.63g(93mmol)、APDS0.75g(3mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、BTA19.81g(100mmol)、NMP15.00gを添加し、40℃で1h、ついで4-アミノ安息香酸(東京化成工業(株)製、以下、4ABA)1.10g(8mmol)を添加し、さらに40℃で1h反応させた。ついで、反応中に発生する水を留去しながら200℃で6h重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Kの固体を得た。樹脂Kの重量平均分子量は30000であった。
TDA-100 30.00g(100mmol)の代わりに、2,2-ビス(3,4-ジカルボキシフェニル)ヘキサフルオロプロパン二無水物(東京化成工業(株)製、以下、6FDA)44.42(100mmol)を用いた以外は合成例4と同様にして樹脂Lの固体を得た。樹脂Lの重量平均分子量は65000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gに3,5-ジアミノ安息香酸(東京化成工業(株)製、以下、DAB)14.44g(95mmol)、1,3-ビス-3-アミノプロピルテトラメチルジシロキサン(東レダウコーニングシリコーン(株)製、商品名「APDS」)1.24g(5mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、ODPA31.02g(100mmol)、NMP15.00gを添加し、40℃で1h、ついで反応中に発生する水を留去しながら200℃で6h重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Mの固体を得た。樹脂Mの重量平均分子量は48000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gにMBAA28.63g(100mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、溶液の温度を10℃以下に保ちながら、イソフタロイルクロリド(東京化成工業(株)製、以下、IPC)20.30(100mmol)、NMP15.00gを添加し、10℃以下で1時間、ついで23℃で6時間重合反応させた。反応終了後、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Nの固体を得た。樹脂Nの重量平均分子量は30000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gにMBAA27.20g(95mmol)、パラフェニレンジアミン(東京化成工業(株)製、以下、PDA)0.54g(5mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、BTA19.81g(100mmol)、NMP15.00gを添加し、40℃で2h反応させた。ついで、反応中に発生する水を留去しながら200℃で6h重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Oの固体を得た。樹脂Oの重量平均分子量は35000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gにMBAA27.20g(95mmol)、PDA0.43g(4mmol)、2,2’-オキシビス(エチルアミン)(東京化成工業(株)製、以下、OBEA)0.10g(1mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、BTA19.81g(100mmol)、NMP15.00gを添加し、40℃で2h反応させた。ついで、反応中に発生する水を留去しながら200℃で6h重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Pの固体を得た。樹脂Pの重量平均分子量は35000であった。
よく乾燥させた四ツ口フラスコの中で、NMP131.79gにMBAA27.20g(95mmol)、PDA0.32g(3mmol)、OBEA0.10g(1mmol)を窒素雰囲気下で撹拌しながら室温で溶解させた。その後、BTA19.81g(100mmol)、NMP15.00gを添加し、40℃で1h、ついで4ABA0.28g(2mmol)を添加し、さらに40℃で1h反応させた。ついで、反応中に発生する水を留去しながら200℃で6h重合反応させた。反応終了後室温に降温し、この溶液を水3Lに投入し、得られた沈殿を濾別し、水1.5Lで3回洗浄した。洗浄後の固体を50℃の通風オーブンで3日間乾燥させ、樹脂Qの固体を得た。樹脂Qの重量平均分子量は30000であった。
合成例18:樹脂Rの合成
TDA-100 30.00g(100mmol)の代わりに、5-(2,5-ジオキソテトラヒドロフリル)-3-メチル-3-シクロヘキセン-1,2-ジカルボン酸無水物(DIC(株)製、商品名「EPICLON B-4400」)26.42g(100mmol)を用いた以外は合成例4と同様にして樹脂Rの固体を得た。樹脂Rの重量平均分子量は20000であった。
粒径約10μmの天然黒鉛50g(富士黒鉛(株)製、CBF1)と、ナノシリコン粉末60g(アルドリッチ社製)と、カーボンブラック10g(三菱化学(株)製、3050)とを混合し、ボールミル中600回転で12時間よく分散させ、その後、80℃で12時間真空乾燥して、シリコン-炭素の混合負極活物質を得た。
表1記載のように、樹脂、塩基性化合物および水を混合して、固形分濃度15質量%の水溶液を調整した。水溶液1~21の各組成、および水溶液のpH値を表2に示す。
表2に記載の水溶液の安定性評価、および、それら水溶液から作製したスラリーを用いて得られた膜の膜特性を評価した。評価結果を表3に示す。
表2に記載の水溶液から作製したスラリーを用いて得られた膜の電池特性を評価した。評価結果を表4に示す。
合成例15で得たリチウムイオン電池用負極活物質80質量部と、ポリフッ化ビニリデン(キシダ化学製、以下、PVdF)15質量部と、導電助剤としてアセチレンブラック5質量部と、NMP100質量部を混合分散し、固形分50質量%のスラリーを得た。このスラリーを用いて行った電池特性評価結果を表4に示す。
Claims (21)
- (a)ポリイミド、ポリアミドイミドおよびポリベンゾオキサゾールのうち少なくとも1種を含む樹脂であって、側鎖に、フェノール性水酸基、カルボキシル基およびスルホン酸基のうち少なくとも1つの酸性官能基を有し、該酸性官能基の濃度が3.4モル/kg以上である樹脂と、(b)塩基性化合物を含む樹脂組成物。
- 固形分濃度15質量%で水に溶解させたときのpHが4~12である請求項1記載の樹脂組成物。
- さらに、(c)水を含み、pHが4~12である請求項1または2に記載の樹脂組成物。
- 前記(a)の樹脂に含まれる一般式(1)で表される構造の総数中、R1が芳香族骨格を有する構造のものを20モル%以上含む、請求項4または5に記載の樹脂組成物。
- 前記(b)塩基性化合物の含有量が、前記(a)の樹脂の前記酸性官能基100モル%に対して20~450モル%である、請求項1~10のいずれかに記載の樹脂組成物。
- 前記(b)塩基性化合物が、アルカリ金属から選ばれる少なくとも1つの元素を含む、請求項1~11のいずれかに記載の樹脂組成物。
- 前記(c)水が、樹脂組成物に含まれる溶媒のうちの80質量%以上を占める、請求項3に記載の樹脂組成物。
- さらに(d)フィラーを含有する、請求項1~12のいずれかに記載の樹脂組成物。
- 前記(d)フィラーが、炭素、マンガン、アルミニウム、バリウム、コバルト、ニッケル、鉄、ケイ素、チタン、スズ、およびゲルマニウムのうち少なくとも1種類の原子を含む、請求項14記載の樹脂組成物。
- 前記(d)フィラーが、シリコン、酸化シリコン、チタン酸リチウム、シリコンカーバイド、それらのうち2つ以上の混合体、それらのうち1つないしは2つ以上の混合体と炭素との混合体、およびそれらのうち1つないしは2つ以上の混合体の表面がカーボンコートされたもの、のうち少なくとも1種類を含む、請求項14または15に記載の樹脂組成物。
- 基材の少なくとも片面に、請求項1~16のいずれかに記載の樹脂組成物から製膜された層を有する、積層体。
- 請求項1~16のいずれかに記載の樹脂組成物を、基材の片面または両面に塗布し塗布膜を形成する工程、および前記塗布膜を乾燥する工程を含む、積層体の製造方法。
- 請求項17に記載の積層体を含む電極。
- 請求項19に記載の電極を含む、二次電池。
- 請求項19に記載の電極を含む、電気二重層キャパシタ。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201880045181.6A CN110809607B (zh) | 2017-07-07 | 2018-06-26 | 树脂组合物、层叠体和其制造方法、电极、二次电池以及双电层电容器 |
KR1020207002547A KR102511725B1 (ko) | 2017-07-07 | 2018-06-26 | 수지 조성물, 적층체 및 그의 제조 방법, 전극, 이차 전지 그리고 전기 이중층 캐패시터 |
US16/624,691 US20200131314A1 (en) | 2017-07-07 | 2018-06-26 | Resin composition, laminate and manufacturing method thereof, electrode, secondary battery, and electric double layer capacitor |
JP2018534761A JP7092029B2 (ja) | 2017-07-07 | 2018-06-26 | 樹脂組成物、積層体およびその製造方法、電極、二次電池ならびに電気二重層キャパシタ |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017133334 | 2017-07-07 | ||
JP2017-133334 | 2017-07-07 | ||
JP2018078909 | 2018-04-17 | ||
JP2018-078909 | 2018-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2019009135A1 true WO2019009135A1 (ja) | 2019-01-10 |
Family
ID=64950903
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2018/024115 WO2019009135A1 (ja) | 2017-07-07 | 2018-06-26 | 樹脂組成物、積層体およびその製造方法、電極、二次電池ならびに電気二重層キャパシタ |
Country Status (6)
Country | Link |
---|---|
US (1) | US20200131314A1 (ja) |
JP (1) | JP7092029B2 (ja) |
KR (1) | KR102511725B1 (ja) |
CN (1) | CN110809607B (ja) |
TW (1) | TWI783002B (ja) |
WO (1) | WO2019009135A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114026178A (zh) * | 2019-08-19 | 2022-02-08 | Jsr株式会社 | 分散组合物、分散剂、各向异性膜及其制造方法、以及各向异性膜形成装置 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102646855B1 (ko) * | 2020-03-20 | 2024-03-11 | 삼성에스디아이 주식회사 | 코팅층 조성물, 이로부터 형성된 코팅층을 포함하는 리튬 이차 전지용 분리막 및 이를 포함하는 리튬 이차 전지 |
CN113667303B (zh) * | 2021-08-20 | 2023-09-29 | 杭州福斯特电子材料有限公司 | 一种树脂组合物及其应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5562926A (en) * | 1978-11-02 | 1980-05-12 | Tokyo Tokushu Densen Toryo Kk | Production of water-soluble polyimide resin |
JP2007086763A (ja) * | 2005-08-24 | 2007-04-05 | Asahi Kasei Corp | 感光性樹脂組成物及びそれを用いた回路基板 |
JP2011137063A (ja) * | 2009-12-28 | 2011-07-14 | Toray Ind Inc | ポリイミド樹脂水溶液、ポリイミド系樹脂水溶液、ポリアゾール樹脂水溶液 |
JP2014172937A (ja) * | 2013-03-06 | 2014-09-22 | Nippon Kodoshi Corp | ポリアミドイミド樹脂材料及びポリアミドイミド樹脂溶液 |
JP2015204133A (ja) * | 2014-04-10 | 2015-11-16 | 株式会社カネカ | 水系バインダ組成物 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4497732B2 (ja) | 2001-02-05 | 2010-07-07 | 宇部興産株式会社 | 水溶性ポリイミド前駆体、ポリイミド前駆体水溶液、その製法およびポリイミド |
JP5374885B2 (ja) | 2008-02-19 | 2013-12-25 | 日産自動車株式会社 | リチウムイオン電池 |
JP5361233B2 (ja) | 2008-03-31 | 2013-12-04 | 三洋電機株式会社 | リチウム二次電池及びその製造方法 |
US20150017370A1 (en) * | 2011-09-12 | 2015-01-15 | Toray Industries, Inc. | Polyimide resin, resin composition and laminated film that use same |
CN108368263B (zh) | 2015-12-09 | 2021-03-12 | 东丽株式会社 | 树脂、浆料、以及使用其得到的层叠体和其制造方法 |
-
2018
- 2018-06-26 CN CN201880045181.6A patent/CN110809607B/zh active Active
- 2018-06-26 WO PCT/JP2018/024115 patent/WO2019009135A1/ja active Application Filing
- 2018-06-26 KR KR1020207002547A patent/KR102511725B1/ko active IP Right Grant
- 2018-06-26 US US16/624,691 patent/US20200131314A1/en not_active Abandoned
- 2018-06-26 JP JP2018534761A patent/JP7092029B2/ja active Active
- 2018-07-04 TW TW107123033A patent/TWI783002B/zh active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5562926A (en) * | 1978-11-02 | 1980-05-12 | Tokyo Tokushu Densen Toryo Kk | Production of water-soluble polyimide resin |
JP2007086763A (ja) * | 2005-08-24 | 2007-04-05 | Asahi Kasei Corp | 感光性樹脂組成物及びそれを用いた回路基板 |
JP2011137063A (ja) * | 2009-12-28 | 2011-07-14 | Toray Ind Inc | ポリイミド樹脂水溶液、ポリイミド系樹脂水溶液、ポリアゾール樹脂水溶液 |
JP2014172937A (ja) * | 2013-03-06 | 2014-09-22 | Nippon Kodoshi Corp | ポリアミドイミド樹脂材料及びポリアミドイミド樹脂溶液 |
JP2015204133A (ja) * | 2014-04-10 | 2015-11-16 | 株式会社カネカ | 水系バインダ組成物 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114026178A (zh) * | 2019-08-19 | 2022-02-08 | Jsr株式会社 | 分散组合物、分散剂、各向异性膜及其制造方法、以及各向异性膜形成装置 |
CN114026178B (zh) * | 2019-08-19 | 2024-01-30 | Jsr株式会社 | 分散组合物、分散剂、各向异性膜及其制造方法、以及各向异性膜形成装置 |
Also Published As
Publication number | Publication date |
---|---|
TW201906929A (zh) | 2019-02-16 |
KR20200027517A (ko) | 2020-03-12 |
TWI783002B (zh) | 2022-11-11 |
JPWO2019009135A1 (ja) | 2020-05-07 |
KR102511725B1 (ko) | 2023-03-21 |
CN110809607B (zh) | 2022-05-17 |
US20200131314A1 (en) | 2020-04-30 |
CN110809607A (zh) | 2020-02-18 |
JP7092029B2 (ja) | 2022-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101990168B1 (ko) | 리튬 이온 전지 정극용 수지 조성물 | |
US10703850B2 (en) | Resin composition | |
JP5375597B2 (ja) | ポリイミド樹脂水溶液、ポリイミド系樹脂水溶液、ポリアゾール樹脂水溶液 | |
WO2012008543A1 (ja) | ポリイミド前駆体水溶液組成物、及びポリイミド前駆体水溶液組成物の製造方法 | |
JP7092029B2 (ja) | 樹脂組成物、積層体およびその製造方法、電極、二次電池ならびに電気二重層キャパシタ | |
JP5733355B2 (ja) | ポリイミド系樹脂水溶液 | |
JP6241213B2 (ja) | 電極用バインダー樹脂組成物、電極合剤ペースト、及び電極 | |
WO2018105338A1 (ja) | 蓄電素子用バインダー組成物、蓄電素子用スラリー組成物、電極、電極の製造方法、二次電池および電気二重層キャパシタ | |
JP2018163877A (ja) | バインダ溶液および塗液 | |
CN115052930B (zh) | 树脂组合物、叠层体及其制造方法、电极、二次电池及双电层电容器 | |
JP7042765B2 (ja) | 電極用バインダー樹脂組成物、電極合剤ペースト、及び電極の製造方法 | |
JP2022116646A (ja) | 蓄電デバイス用組成物、蓄電デバイス電極用スラリー、蓄電デバイス電極、及び蓄電デバイス | |
TWI496816B (zh) | 聚醯亞胺前驅體水溶液組成物及聚醯亞胺前驅體水溶液組成物之製造方法 | |
JP5733356B2 (ja) | ポリアゾール樹脂水溶液 | |
JP2016079310A (ja) | 多孔質膜製造用ワニス、それを用いた多孔質膜の製造方法、及び多孔質膜製造用空孔形成剤 | |
WO2021090656A1 (ja) | 表面コート層を有する活物質、それを含む電極および蓄電デバイス | |
JP2022151684A (ja) | スラリー組成物、電極、ならびにそれを含む二次電池および電気二重層キャパシタ |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
ENP | Entry into the national phase |
Ref document number: 2018534761 Country of ref document: JP Kind code of ref document: A |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 18828416 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20207002547 Country of ref document: KR Kind code of ref document: A |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 18828416 Country of ref document: EP Kind code of ref document: A1 |