JP2016065142A - Dispersant for carbon material - Google Patents
Dispersant for carbon material Download PDFInfo
- Publication number
- JP2016065142A JP2016065142A JP2014194583A JP2014194583A JP2016065142A JP 2016065142 A JP2016065142 A JP 2016065142A JP 2014194583 A JP2014194583 A JP 2014194583A JP 2014194583 A JP2014194583 A JP 2014194583A JP 2016065142 A JP2016065142 A JP 2016065142A
- Authority
- JP
- Japan
- Prior art keywords
- carbon material
- weight
- mol
- dispersant
- examples
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003575 carbonaceous material Substances 0.000 title claims abstract description 55
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 36
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 239000006185 dispersion Substances 0.000 claims abstract description 25
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920001577 copolymer Polymers 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000000470 constituent Substances 0.000 claims abstract description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 229920005604 random copolymer Polymers 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 24
- -1 acrylic nitrile Chemical class 0.000 abstract description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007810 chemical reaction solvent Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229930195735 unsaturated hydrocarbon Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical class CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000569 multi-angle light scattering Methods 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- HDKLIZDXVUCLHQ-BQYQJAHWSA-N (3E)-3-nonen-2-one Chemical compound CCCCC\C=C\C(C)=O HDKLIZDXVUCLHQ-BQYQJAHWSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- AJPUEYRSXFAFHV-UHFFFAOYSA-N (4-ethenylphenoxy)-oxoborane Chemical compound C=CC1=CC=C(OB=O)C=C1 AJPUEYRSXFAFHV-UHFFFAOYSA-N 0.000 description 1
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HDKLIZDXVUCLHQ-UHFFFAOYSA-N (E)-3-Nonen-2-one Natural products CCCCCC=CC(C)=O HDKLIZDXVUCLHQ-UHFFFAOYSA-N 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- 239000001764 (E)-oct-3-en-2-one Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- QOVCUELHTLHMEN-UHFFFAOYSA-N 1-butyl-4-ethenylbenzene Chemical compound CCCCC1=CC=C(C=C)C=C1 QOVCUELHTLHMEN-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- LVJZCPNIJXVIAT-UHFFFAOYSA-N 1-ethenyl-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C=C)C(F)=C1F LVJZCPNIJXVIAT-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- JWVTWJNGILGLAT-UHFFFAOYSA-N 1-ethenyl-4-fluorobenzene Chemical compound FC1=CC=C(C=C)C=C1 JWVTWJNGILGLAT-UHFFFAOYSA-N 0.000 description 1
- KWHSBYQFELZKKS-UHFFFAOYSA-N 1-ethenyl-4-iodobenzene Chemical compound IC1=CC=C(C=C)C=C1 KWHSBYQFELZKKS-UHFFFAOYSA-N 0.000 description 1
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 1
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- DUIIPHYNGUDOIM-UHFFFAOYSA-N 2-(4-ethenylphenyl)acetonitrile Chemical compound C=CC1=CC=C(CC#N)C=C1 DUIIPHYNGUDOIM-UHFFFAOYSA-N 0.000 description 1
- PYKCEDJHRUUDRK-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2-methylpropanenitrile Chemical compound CC(C)(C)N=NC(C)(C)C#N PYKCEDJHRUUDRK-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MNCGMVDMOKPCSQ-UHDJGPCESA-M sodium;(e)-2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)\C=C\C1=CC=CC=C1 MNCGMVDMOKPCSQ-UHDJGPCESA-M 0.000 description 1
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N trans-beta-methyl styrene Natural products CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
本発明は、炭素材料用分散剤に関する。 The present invention relates to a dispersant for carbon materials.
カーボンブラックなどの炭素材料は、塗料、インキ、筆記具、化粧料などの黒色顔料として使用されている。これらの炭素材料は分散体として使用されることが多く、これを分散し得る分散剤の検討が行われている。例えば、特許文献1では、ポリビニルアルコール、ポリビニルピロリドン、ポリエチレンオキシドなどを分散剤として使用することが開示されている。 Carbon materials such as carbon black are used as black pigments for paints, inks, writing instruments, cosmetics and the like. These carbon materials are often used as a dispersion, and a dispersant capable of dispersing the carbon material has been studied. For example, Patent Document 1 discloses the use of polyvinyl alcohol, polyvinyl pyrrolidone, polyethylene oxide, or the like as a dispersant.
しかしながら、これらの分散剤を用いて得られる炭素材料分散体は、これを乾燥して得られる乾燥物の耐溶媒性が悪いという問題がある。具体的には、前記乾燥物に、水、エタノールまたはエチレンカーボネートなどの様々な溶媒が接触した場合、炭素材料や分散剤が該溶媒中に溶出するため、インキなどとして用いた場合には滲みなどが発生するという問題がある。 However, the carbon material dispersion obtained by using these dispersants has a problem that the dried product obtained by drying the dispersion has poor solvent resistance. Specifically, when various solvents such as water, ethanol or ethylene carbonate come into contact with the dried product, the carbon material and the dispersant are eluted in the solvent, so that when used as an ink, bleeding, etc. There is a problem that occurs.
そこで、本発明は、炭素材料の分散性に優れるとともに、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性に優れる炭素材料用分散剤を提供することを課題とする。 Then, this invention makes it a subject to provide the dispersing agent for carbon materials which is excellent in the dispersibility of a carbon material, and is excellent in the solvent resistance of the dried material obtained by drying a carbon material dispersion.
上記課題を解決すべく、本発明に係る炭素材料用分散剤は、構成モノマーとして少なくともアクリロニトリル(A)およびN−ビニルピロリドン(B)を有する共重合体を含有するものであり、上記構成モノマーにおけるアクリロニトリル(A)の割合が50〜99モル%であり、N−ビニルピロリドン(B)の割合が1〜30モル%である。 In order to solve the above-mentioned problem, the dispersant for carbon material according to the present invention contains a copolymer having at least acrylonitrile (A) and N-vinylpyrrolidone (B) as constituent monomers. The proportion of acrylonitrile (A) is 50 to 99 mol%, and the proportion of N-vinylpyrrolidone (B) is 1 to 30 mol%.
かかる構成によれば、炭素材料の分散性に優れるとともに、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性が優れたものとなる。 According to this configuration, the carbon material is excellent in dispersibility, and the solvent resistance of the dried product obtained by drying the carbon material dispersion is excellent.
本発明によれば、炭素材料の分散性に優れるとともに、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性が優れるという効果を奏する。 ADVANTAGE OF THE INVENTION According to this invention, while being excellent in the dispersibility of a carbon material, there exists an effect that the solvent resistance of the dried material obtained by drying a carbon material dispersion is excellent.
以下、本発明の好ましい実施の形態について説明する。 Hereinafter, preferred embodiments of the present invention will be described.
本発明に係る炭素材料用分散剤は、構成モノマーとして少なくともアクリロニトリル(A)およびN−ビニルピロリドン(B)を有する共重合体を含有するものである。 The dispersant for carbon material according to the present invention contains a copolymer having at least acrylonitrile (A) and N-vinylpyrrolidone (B) as constituent monomers.
本発明に用いるアクリロニトリル(A)の構成モノマーにおける割合は、50モル%以上であり、60モル%以上であることが好ましく、70モル%以上であることがより好ましい。また、上記割合は、99モル%以下であり、97モル%以下であることが好ましく、95モル%以下であることがより好ましい。アクリロニトリル(A)の割合を上記範囲内とすることにより、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性が優れたものとなる。 The proportion of the acrylonitrile (A) used in the present invention in the constituent monomer is 50 mol% or more, preferably 60 mol% or more, and more preferably 70 mol% or more. Moreover, the said ratio is 99 mol% or less, it is preferable that it is 97 mol% or less, and it is more preferable that it is 95 mol% or less. By making the ratio of acrylonitrile (A) in the said range, the solvent resistance of the dried material obtained by drying a carbon material dispersion will become excellent.
本発明に用いるN−ビニルピロリドン(B)の構成モノマーにおける割合は、1モル%以上であり、3モル%以上であることが好ましく、5モル%以上であることがより好ましい。また、上記割合は、30モル%以下であり、20モル%以下であることが好ましく、15モル%以下であることがより好ましく、10モル%以下であることがさらに好ましい。N−ビニルピロリドン(B)の割合を上記範囲内とすることにより、炭素材料の分散性に優れるとともに、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性が優れたものとなる。 The proportion of N-vinylpyrrolidone (B) used in the present invention in the constituent monomer is 1 mol% or more, preferably 3 mol% or more, and more preferably 5 mol% or more. Moreover, the said ratio is 30 mol% or less, It is preferable that it is 20 mol% or less, It is more preferable that it is 15 mol% or less, It is further more preferable that it is 10 mol% or less. By setting the ratio of N-vinylpyrrolidone (B) within the above range, the dispersibility of the carbon material is excellent, and the solvent resistance of the dried product obtained by drying the carbon material dispersion is excellent.
アクリロニトリル(A)1モルに対するN−ビニルピロリドン(B)の割合は、0.01モル以上であることが好ましく、0.03モル%以上であることがより好ましく、0.05モル以上であることがさらに好ましい。また、上記割合は、0.3モル以下であることが好ましく、0.2モル以下であることがより好ましく、0.15モル以下であることがさらに好ましい。N−ビニルピロリドン(B)の割合を上記範囲内とすることにより、炭素材料の分散性に優れるとともに、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性が優れたものとなる。 The ratio of N-vinylpyrrolidone (B) to 1 mol of acrylonitrile (A) is preferably 0.01 mol or more, more preferably 0.03 mol% or more, and 0.05 mol or more. Is more preferable. Further, the ratio is preferably 0.3 mol or less, more preferably 0.2 mol or less, and further preferably 0.15 mol or less. By setting the ratio of N-vinylpyrrolidone (B) within the above range, the dispersibility of the carbon material is excellent, and the solvent resistance of the dried product obtained by drying the carbon material dispersion is excellent.
前記共重合体は、本発明の効果を阻害しない範囲内で、アクリロニトリル(A)およびN−ビニルピロリドン(B)以外のモノマー(C)を含んでいてもよい。このようなモノマー(C)としては、例えば、α,β−不飽和カルボン酸及びその誘導体、α,β−不飽和ケトン、不飽和炭化水素化合物、シアノ基含有不飽和炭化水素化合物、ビニルエーテル化合物、ビニルエステル化合物、不飽和アルコール化合物、芳香族アルケニル化合物、並びに、炭素数7以上のN−ビニルアミン化合物などが挙げられる。ここで、芳香族アルケニル化合物とは、アルケニル基で置換された芳香環を有する化合物である。また、N−アルケニルアミン化合物とは、窒素原子上にアルケニル基を有する化合物である。 The copolymer may contain a monomer (C) other than acrylonitrile (A) and N-vinylpyrrolidone (B) as long as the effects of the present invention are not impaired. Examples of such a monomer (C) include α, β-unsaturated carboxylic acids and derivatives thereof, α, β-unsaturated ketones, unsaturated hydrocarbon compounds, cyano group-containing unsaturated hydrocarbon compounds, vinyl ether compounds, Examples thereof include vinyl ester compounds, unsaturated alcohol compounds, aromatic alkenyl compounds, and N-vinylamine compounds having 7 or more carbon atoms. Here, the aromatic alkenyl compound is a compound having an aromatic ring substituted with an alkenyl group. The N-alkenylamine compound is a compound having an alkenyl group on the nitrogen atom.
α,β−不飽和カルボン酸としては、例えば、(メタ)アクリル酸、クロトン酸、けい皮酸、マレイン酸、フマル酸、イタコン酸、トランス−2−ヘキサン酸などが挙げられる。なお、本明細書において、(メタ)アクリル酸は、アクリル酸またはメタクリル酸を意味する。 Examples of the α, β-unsaturated carboxylic acid include (meth) acrylic acid, crotonic acid, cinnamic acid, maleic acid, fumaric acid, itaconic acid, trans-2-hexanoic acid and the like. In the present specification, (meth) acrylic acid means acrylic acid or methacrylic acid.
α,β−不飽和カルボン酸の誘導体としては、α,β−不飽和カルボン酸塩、α,β−不飽和カルボン酸無水物、α,β−不飽和カルボン酸クロリド、α,β−不飽和カルボン酸エステル、α,β−不飽和カルボン酸アミド、マレイミド化合物等が挙げられる。 The derivatives of α, β-unsaturated carboxylic acid include α, β-unsaturated carboxylate, α, β-unsaturated carboxylic acid anhydride, α, β-unsaturated carboxylic acid chloride, α, β-unsaturated. Examples thereof include carboxylic acid esters, α, β-unsaturated carboxylic acid amides, maleimide compounds and the like.
α,β−不飽和カルボン酸塩としては、例えば、上記α,β−不飽和カルボン酸のナトリウム塩、カリウム塩などが挙げられる。α,β−不飽和カルボン酸無水物としては、例えば、上記α,β−不飽和カルボン酸の無水物が挙げられる。α,β−不飽和カルボン酸クロリドとしては、例えば、上記α,β−不飽和カルボン酸のカルボン酸クロライドが挙げられる。α,β−不飽和カルボン酸エステルとしては、例えば、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸プロピル、(メタ)アクリル酸−n−ブチル、(メタ)アクリル酸−t−ブチル、(メタ)アクリル酸ヘキシル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸デシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸テトラヒドロフルフリル、(メタ)アクリル酸アリル、(メタ)アクリル酸ビニル、(メタ)アクリル酸フェニル、(メタ)アクリル酸ベンジル、グリシジル(メタ)アクリレート、(メタ)アクリル酸2−ジメチルアミノエチル、(メタ)アクリル酸2−エトキシエチル、(メタ)アクリル酸2−ヒドロキシエチルなどが挙げられる。α,β−不飽和カルボン酸アミドとしては、例えば、(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド、N−(t−ブチル)(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N−(3−ジメチルアミノプロピル)(メタ)アクリルアミド、クロトンアミドなどが挙げられる。マレイミド化合物としては、例えば、マレイミド、N−メチルマレイミド、N−エチルマレイミド、N−フェニルマレイミドなどが挙げられる。 Examples of the α, β-unsaturated carboxylate include the sodium salt and potassium salt of the α, β-unsaturated carboxylic acid. Examples of the α, β-unsaturated carboxylic acid anhydride include anhydrides of the above α, β-unsaturated carboxylic acid. Examples of the α, β-unsaturated carboxylic acid chloride include carboxylic acid chlorides of the above α, β-unsaturated carboxylic acids. Examples of the α, β-unsaturated carboxylic acid ester include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, (n-butyl) (meth) acrylate, and (meth) acrylic acid. -T-butyl, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, cyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate Allyl (meth) acrylate, vinyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, glycidyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, (meth) acrylic Examples include 2-ethoxyethyl acid and 2-hydroxyethyl (meth) acrylate. Examples of the α, β-unsaturated carboxylic acid amide include (meth) acrylamide, N-methyl (meth) acrylamide, N- (t-butyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N -Methylol (meth) acrylamide, N- (3-dimethylaminopropyl) (meth) acrylamide, crotonamide, etc. are mentioned. Examples of maleimide compounds include maleimide, N-methylmaleimide, N-ethylmaleimide, N-phenylmaleimide and the like.
α,β−不飽和ケトンとしては、例えば、イソプロピリデンアセトン、ジイソプロピリデンアセトン、2−シクロヘキセン−1−オン、2−シクロペンテン−1−オン、3−デセン−2−オン、3−メチル−3−ブテン−2−オン、メチルビニルケトン、3−ノネン−2−オン、3−オクテン−2−オンなどが挙げられる。 Examples of the α, β-unsaturated ketone include isopropylideneacetone, diisopropylideneacetone, 2-cyclohexen-1-one, 2-cyclopenten-1-one, 3-decene-2-one, and 3-methyl-3. -Buten-2-one, methyl vinyl ketone, 3-nonen-2-one, 3-octen-2-one and the like.
不飽和炭化水素化合物としては、例えば、エチレン、プロペン、1−ブテン、2−ブテン、イソブテン、1−ペンテン、1−ヘキセン及び1−オクテンなどのアルケン、1,3−ブタジエン、イソプレン、1,3−ペンタジエン、1,3−ヘキサジエン、1,3−シクロヘキサジエン、1,3−シクロヘプタジエン、1,3−シクロオクタジエン、2,5−ジメチル−2,4−ヘキサジエン及びクロロプレンなどの共役ジエンが挙げられる。 Examples of unsaturated hydrocarbon compounds include ethylene, propene, 1-butene, 2-butene, isobutene, 1-pentene, 1-hexene, 1-octene and other alkenes, 1,3-butadiene, isoprene, 1,3 Conjugated dienes such as pentadiene, 1,3-hexadiene, 1,3-cyclohexadiene, 1,3-cycloheptadiene, 1,3-cyclooctadiene, 2,5-dimethyl-2,4-hexadiene and chloroprene; Can be mentioned.
シアノ基含有不飽和炭化水素化合物としては、例えば、メタクリロニトリル、α−クロロアクリロニトリル、α−シアノエチルアクリロニトリルなどが挙げられる。 Examples of the cyano group-containing unsaturated hydrocarbon compound include methacrylonitrile, α-chloroacrylonitrile, α-cyanoethylacrylonitrile, and the like.
ビニルエーテル化合物としては、例えば、ビニルエチルエーテル、ビニルブチルエーテル、ビニルフェニルエーテル、ビニル2−クロロエチルエーテル、3,4−ジヒドロ−2H−ピラン、2,3−ジヒドロフラン、1,4−ジオキセン、エチレングリコールモノビニルエーテル、ジエチレングリコールモノビニルエーテル、イソプロペニルメチルエーテルなどが挙げられる。 Examples of the vinyl ether compound include vinyl ethyl ether, vinyl butyl ether, vinyl phenyl ether, vinyl 2-chloroethyl ether, 3,4-dihydro-2H-pyran, 2,3-dihydrofuran, 1,4-dioxene, ethylene glycol. Examples thereof include monovinyl ether, diethylene glycol monovinyl ether, and isopropenyl methyl ether.
ビニルエステル化合物としては、例えば、酢酸ビニル、酪酸ビニル、酢酸イソプロペニル、カプリン酸ビニル、安息香酸ビニルなどが挙げられる。 Examples of the vinyl ester compound include vinyl acetate, vinyl butyrate, isopropenyl acetate, vinyl caprate, vinyl benzoate and the like.
不飽和アルコールとしては、例えば、アリルアルコール、けい皮アルコールなどが挙げられる。 Examples of the unsaturated alcohol include allyl alcohol and cinnamic alcohol.
芳香族ビニル化合物としては、例えば、スチレン、2−メチルスチレン、3−メチルスチレン、4−メチルスチレン、2,4,6−トリメチルスチレン、4−ブチルスチレン、4−フェニルスチレン、4−フルオロスチレン、2,3,4,5,6−ペンタフルオロスチレン、4−クロロスチレン、4−ブロモスチレン、4−ヨードスチレン、4−ヒドロキシスチレン、4−アミノスチレン、4−カルボキシスチレン、4−アセトキシスチレン、4−シアノメチルスチレン、4−クロロメチルスチレン、4−メトキシスチレン、4−ニトロスチレン、4−スチレンスルホン酸ナトリウム、4−スチレンスルホン酸クロリド、4−ビニルフェニルボラン酸、α−メチルスチレン、トランス−β−メチルスチレン、2−メチル−1−フェニルプロペン、1−フェニル−1−シクロヘキセン、β−ブロモスチレン、β−スチレンスルホン酸ナトリウム、2−ビニルピリジン、4−ビニルピリジン、2−イソプロペニルナフタレン、1−ビニルイミダゾールなどの芳香族ビニル化合物が挙げられる。 Examples of the aromatic vinyl compound include styrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2,4,6-trimethylstyrene, 4-butylstyrene, 4-phenylstyrene, 4-fluorostyrene, 2,3,4,5,6-pentafluorostyrene, 4-chlorostyrene, 4-bromostyrene, 4-iodostyrene, 4-hydroxystyrene, 4-aminostyrene, 4-carboxystyrene, 4-acetoxystyrene, 4 -Cyanomethylstyrene, 4-chloromethylstyrene, 4-methoxystyrene, 4-nitrostyrene, sodium 4-styrenesulfonate, 4-styrenesulfonic acid chloride, 4-vinylphenylboranoic acid, α-methylstyrene, trans-β -Methylstyrene, 2-methyl-1-phenylpropene Aromatic vinyl compounds such as 1-phenyl-1-cyclohexene, β-bromostyrene, sodium β-styrenesulfonate, 2-vinylpyridine, 4-vinylpyridine, 2-isopropenylnaphthalene, and 1-vinylimidazole. .
炭素数7以上のN−ビニルアミン化合物としては、例えば、N−ビニルカプロラクタム、N−ビニルカルバゾールなどが挙げられる。 Examples of the N-vinylamine compound having 7 or more carbon atoms include N-vinylcaprolactam and N-vinylcarbazole.
前記モノマー(C)を用いる場合、構成モノマーに対する割合は、0.1モル以上であることが好ましく、1モル%以上であることがより好ましい。また、上記割合は、40モル%以下であることが好ましく、30モル%以下であることがより好ましく、20モル%以下であることがさらに好ましい。 When using the said monomer (C), it is preferable that the ratio with respect to a structural monomer is 0.1 mol or more, and it is more preferable that it is 1 mol% or more. The proportion is preferably 40 mol% or less, more preferably 30 mol% or less, and further preferably 20 mol% or less.
前記共重合体は、重量平均分子量が1万以上であることが好ましく、2万以上であることがより好ましい。また、上記重量平均分子量は、50万以下であることが好ましく、30万以下であることがより好ましい。重量平均分子量を上記範囲内とすることにより、炭素材料の分散性に優れるとともに、炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性が優れたものとなる。 The copolymer preferably has a weight average molecular weight of 10,000 or more, and more preferably 20,000 or more. The weight average molecular weight is preferably 500,000 or less, and more preferably 300,000 or less. By setting the weight average molecular weight within the above range, the dispersibility of the carbon material is excellent, and the solvent resistance of the dried product obtained by drying the carbon material dispersion is excellent.
本発明の共重合体の製造方法は特に限定されないが、例えば、ラジカル重合法、アニオン重合法、カチオン重合法など、種々の重合法を用いることができる。これらのうち、反応が簡便であることから、ラジカル重合法が好ましい。 Although the manufacturing method of the copolymer of this invention is not specifically limited, For example, various polymerization methods, such as a radical polymerization method, an anionic polymerization method, and a cationic polymerization method, can be used. Of these, the radical polymerization method is preferred because the reaction is simple.
ラジカル重合法は、溶液重合法、エマルジョン重合法、バルク重合法、懸濁重合法等のいずれの方法でも行うことができる。また、単量体の供給方法としては、バッチ法、半バッチ法、連続法、逐次供給法等のいずれも採用可能である。 The radical polymerization method can be performed by any method such as a solution polymerization method, an emulsion polymerization method, a bulk polymerization method, and a suspension polymerization method. Moreover, as a monomer supply method, any of a batch method, a semi-batch method, a continuous method, a sequential supply method, and the like can be employed.
重合反応溶媒は、使用する単量体の種類に応じて適宜選択することができる。例えば、水、メタノール、エタノール、2−プロパノール及び2−ブタノールなどのアルコール、アセトニトリルなどのニトリル化合物、トルエン、キシレン及び石油ナフサなどの芳香族炭化水素、メチルアミルケトン、メチルイソブチルケトン、メチルエチルケトン及びアセトンなどのケトン系溶媒、酢酸ブチル及び酢酸ヘキシルなどのエステル系溶媒、1,2−ジメトキシエタン、テトラヒドロフラン及びジオキサンなどのエーテル系溶媒、プロピレングリコールモノメチルエーテル酢酸エステルなどのグリコールエーテルエステルなどが挙げられる。 The polymerization reaction solvent can be appropriately selected according to the type of monomer used. For example, water, alcohols such as methanol, ethanol, 2-propanol and 2-butanol, nitrile compounds such as acetonitrile, aromatic hydrocarbons such as toluene, xylene and petroleum naphtha, methyl amyl ketone, methyl isobutyl ketone, methyl ethyl ketone and acetone Ketone solvents, ester solvents such as butyl acetate and hexyl acetate, ether solvents such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, and glycol ether esters such as propylene glycol monomethyl ether acetate.
反応溶液からの共重合体の単離は、公知の方法で行うことができる。例えば、反応溶媒や未反応モノマーを除去し、不溶性の溶媒を用いて析出させることにより単離することができる。また、生成物の単離が不要である場合は、反応溶液をそのまま使用することも可能である。 Isolation of the copolymer from the reaction solution can be performed by a known method. For example, it can be isolated by removing the reaction solvent and unreacted monomers and precipitating with an insoluble solvent. Moreover, when isolation of a product is unnecessary, it is also possible to use a reaction solution as it is.
ラジカル重合開始剤としては、従来公知の化合物が使用でき、例えば、t−ブチルヒドロペルオキシド、クメンヒドロペルオキシド、ペルオキシ酢酸t−ブチル、ペルオキシ安息香酸t−ブチル、ペルオキシオクタン酸t−ブチル、ペルオキシネオデカン酸t−ブチル、ペルオキシイソ酪酸t−ブチル、過酸化ラウロイル、ペルオキシピバリン酸t−アミル、ペルオキシピバリン酸t−ブチル、過酸化ジクミル、過酸化ベンゾイル、過硫酸カリウム及び過硫酸アンモニウムなどの過酸化水素類、2,2’−アゾビス(イソブチロニトリル)、2,2’−アゾビス(2−ブテノニトリル)、4,4’−アゾビス(4−ペンタン酸)、1,1’−アゾビス(シクロヘキサンカルボニトリル)、2−(t−ブチルアゾ)−2−シアノプロパン、2,2’−アゾビス[2−メチル−N−(1,1)−ビス(ヒドロキシメチル)−2−ヒドロキシエチル]プロピオンアミド、2,2’−アゾビス(2−メチル−N−ヒドロキシエチル)プロピオンアミド、二塩化2,2’−アゾビス(N,N’−ジメチレンイソブチルアミジン)、二塩化2,2’−アゾビス(2−アミジノプロパン)、2,2’−アゾビス(N,N’−ジメチレンイソブチルアミド)、2,2’−アゾビス(2−メチル−N−[1,1−ビス(ヒドロキシメチル)−2−ヒドロキシエチル]プロピオンアミド)、2,2’−アゾビス(2−メチル−N−[1,1−ビス(ヒドロキシメチル)エチル]プロピオンアミド)、2,2’−アゾビス[2−メチル−N−(2−ヒドロキシエチル)プロピオンアミド]及び2,2’−アゾビス(イソブチリルアミド)二水和物などのアゾ化合物、過硫酸塩(例えば、過硫酸カリウム、過硫酸ナトリウム及び過硫酸アンモニウムなど)と還元剤(例えば、メタ亜硫酸水素ナトリウム及び亜硫酸水素ナトリウムなど)との組み合わせ、有機過酸化物(例えば、過酸化ベンゾイル及びクメンハイドロパーオキサイドなど)と3級アミン(例えば、ジメチルアニリン及びアニリンなど)との組み合わせ、有機過酸化物(例えば、過酸化ベンゾイル及びクメンハイドロパーオキサイドなど)と遷移金属化合物(例えば、コバルトナフテートなど)との組み合わせなどのレドックス系開始剤が挙げられる。 As the radical polymerization initiator, conventionally known compounds can be used, such as t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyacetate, t-butyl peroxybenzoate, t-butyl peroxyoctanoate, peroxyneodecanoic acid. hydrogen peroxides such as t-butyl, t-butyl peroxyisobutyrate, lauroyl peroxide, t-amyl peroxypivalate, t-butyl peroxypivalate, dicumyl peroxide, benzoyl peroxide, potassium persulfate and ammonium persulfate, 2,2′-azobis (isobutyronitrile), 2,2′-azobis (2-butenonitrile), 4,4′-azobis (4-pentanoic acid), 1,1′-azobis (cyclohexanecarbonitrile), 2- (t-butylazo) -2-cyanopropane, 2, '-Azobis [2-methyl-N- (1,1) -bis (hydroxymethyl) -2-hydroxyethyl] propionamide, 2,2'-azobis (2-methyl-N-hydroxyethyl) propionamide, two 2,2′-azobis chloride (N, N′-dimethyleneisobutylamidine), 2,2′-azobis (2-amidinopropane) dichloride, 2,2′-azobis (N, N′-dimethyleneisobutyramide) ), 2,2′-azobis (2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] propionamide), 2,2′-azobis (2-methyl-N- [1 , 1-bis (hydroxymethyl) ethyl] propionamide), 2,2′-azobis [2-methyl-N- (2-hydroxyethyl) propionamide] and 2,2′-a Azo compounds such as bis (isobutyrylamide) dihydrate, persulfates (eg, potassium persulfate, sodium persulfate and ammonium persulfate) and reducing agents (eg, sodium metabisulfite and sodium bisulfite) In combination with organic peroxides (eg benzoyl peroxide and cumene hydroperoxide) and tertiary amines (eg dimethylaniline and aniline), organic peroxides (eg benzoyl peroxide and cumene) And redox initiators such as a combination of a hydroperoxide and a transition metal compound (for example, cobalt naphthate).
本発明に用いる共重合体としては、ランダム共重合体、ブロック共重合体、グラフト共重合体などが挙げられるが、炭素材料の分散性および炭素材料分散体を乾燥して得られる乾燥物の耐溶媒性がより優れることから、ランダム共重合体が好ましい。 Examples of the copolymer used in the present invention include a random copolymer, a block copolymer, and a graft copolymer, but the dispersibility of the carbon material and the resistance of the dried product obtained by drying the carbon material dispersion. Random copolymers are preferred because of their superior solvent properties.
本発明に係る炭素材料用分散剤には、本発明の効果を阻害しない範囲内で、前記共重合体以外の成分を含有することができる。このような成分としては、例えば、前記共重合体以外の分散剤、分散助剤などが挙げられる。 The dispersant for a carbon material according to the present invention can contain components other than the copolymer as long as the effects of the present invention are not impaired. Examples of such components include dispersants and dispersion aids other than the copolymer.
前記共重合体以外の分散剤としては、例えば、ウレタン系分散剤、ポリエチレンイミン系分散剤、ポリオキシエチレンアルキルエーテル系分散剤、ポリオキシエチレンアルキルフェニルエーテル系分散剤、ポリエチレングリコールジエステル系分散剤、ソルビタン脂肪酸エステル系分散剤、脂肪酸変性ポリエステル系分散剤、アクリル系分散剤などを挙げることができる。 Examples of the dispersant other than the copolymer include a urethane dispersant, a polyethyleneimine dispersant, a polyoxyethylene alkyl ether dispersant, a polyoxyethylene alkyl phenyl ether dispersant, a polyethylene glycol diester dispersant, Examples include sorbitan fatty acid ester dispersants, fatty acid-modified polyester dispersants, acrylic dispersants, and the like.
分散助剤としては、例えば、銅フタロシアニン、ジケトピロロピロール、ノフタロンのスルホン酸誘導体等の顔料誘導体などが挙げられる。 Examples of the dispersion aid include pigment derivatives such as copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of nophthalone.
本発明に係る炭素材料分散体は、炭素材料、前記炭素材料用分散剤および非水系液体を含有するものである。 The carbon material dispersion which concerns on this invention contains a carbon material, the said dispersing agent for carbon materials, and a non-aqueous liquid.
前記炭素材料は、活性炭、黒鉛(グラファイト)、カーボンブラック、カーボンナノファイバー、カーボンナノチューブ、グラフェン、フラーレンなどが挙げられる。 Examples of the carbon material include activated carbon, graphite (graphite), carbon black, carbon nanofiber, carbon nanotube, graphene, fullerene and the like.
また、炭素材料用分散剤の割合は、炭素材料100質量部に対して、10質量部以上500質量部以下であることが好ましい。 Moreover, it is preferable that the ratio of the dispersing agent for carbon materials is 10 to 500 mass parts with respect to 100 mass parts of carbon materials.
前記非水系液体は、水以外の溶媒であれば特に限定されないが、例えば、N−メチルピロリドンなどのラクタム系溶媒、α−アセトラクトン、β−プロピオラクトン、γ−ブチロラクトンおよびδ−バレロラクトンなどのラクトン系溶媒、エチレングリコールモノメチルエーテルアセテートおよびプロピレングリコールモノメチルエーテルアセテートなどのエステル系溶媒、ジメチルホルムアミドおよびジメチルアセトアミドアミド系溶媒、ジメチルスルホキシドなどが挙げられる。これらのうち、前記炭素材料用分散剤の溶解性が良好であることから、N−メチルピロリドン、γ−ブチロラクトン、ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシドおよびプロピレングリコールモノメチルエーテルアセテートが好ましい。 The non-aqueous liquid is not particularly limited as long as it is a solvent other than water. Examples thereof include lactam solvents such as N-methylpyrrolidone, α-acetolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone. Lactone solvents, ester solvents such as ethylene glycol monomethyl ether acetate and propylene glycol monomethyl ether acetate, dimethylformamide and dimethylacetamide amide solvents, dimethyl sulfoxide and the like. Of these, N-methylpyrrolidone, γ-butyrolactone, dimethylformamide, dimethylacetamide, dimethylsulfoxide, and propylene glycol monomethyl ether acetate are preferred because the solubility of the carbon material dispersant is good.
前記非水系液体の使用量は、所望の濃度とするために適宜調整可能であるため特に限定されないが、一般的には、炭素材料1質量部に対して1質量部以上1000質量部以下であることが好ましい。
Although the usage-amount of the said non-aqueous liquid can be suitably adjusted in order to make it a desired density | concentration, it is not specifically limited, Generally, it is 1 to 1000 mass parts with respect to 1 mass part of carbon materials. It is preferable.
本発明に係る炭素材料分散体には、本発明の効果を阻害しない範囲内で、上記以外の成分を含有することができる。このような成分としては、例えば、水、樹脂またはその前駆体、架橋剤、金属酸化物、金属酸塩、炭酸金属塩、粘土鉱物、酸化防止剤、光安定剤、粘度調整剤、着色剤、防腐剤などが挙げられる。 The carbon material dispersion according to the present invention may contain components other than those described above as long as the effects of the present invention are not impaired. Examples of such components include water, resin or precursor thereof, cross-linking agent, metal oxide, metal acid salt, metal carbonate, clay mineral, antioxidant, light stabilizer, viscosity modifier, colorant, Examples include preservatives.
本発明に係る炭素材料含有固体は、前記炭素材料分散体を含む組成物を乾燥して得られる乾燥物である。乾燥方法としては、特に限定される、加熱、減圧など公知の方法を採用することができる。また、得られる炭素材料含有固体が重合または架橋し得る化合物を含む場合は、さらに重合または架橋反応を行ってもよい。
The carbon material-containing solid according to the present invention is a dried product obtained by drying a composition containing the carbon material dispersion. As a drying method, known methods such as heating and decompression can be employed, which are particularly limited. Moreover, when the carbon material containing solid obtained contains the compound which can superpose | polymerize or bridge | crosslink, you may perform superposition | polymerization or a crosslinking reaction further.
本発明について、実施例および比較例に基づいてより具体的に説明するが、本発明はこれに限定されるものではない。当業者は本発明の範囲を逸脱することなく、種々の変更、修正、および改変を行うことができる。 The present invention will be described more specifically based on examples and comparative examples, but the present invention is not limited to this. Those skilled in the art can make various changes, modifications, and alterations without departing from the scope of the present invention.
(製造例1)
窒素導入管、温度計、還流管を取り付けた反応容器に、モノマーとして、N−ビニルピロリドン22.5重量部およびアクリロニトリル127.5重量部、反応溶媒としてN−メチルピロリドン150重量部を仕込み、窒素吹き込みによる脱酸素を行った。続いて、60℃に昇温し、2,2’−アゾビス(2,4−ジメチルバレロニトリル)のN−メチルピロリドン溶液(濃度:2重量%)0.8重量部を添加して反応を開始した。反応開始後、2時間毎に2,2’−アゾビス(2,4−ジメチルバレロニトリル)のN−メチルピロリドン溶液(濃度:2重量%)0.4重量部を添加し、合計20時間反応させた。ここに、固形分濃度が20重量%となるようにN−メチルピロリドンを添加することにより、重合体1のN−メチルピロリドン溶液を得た。
(Production Example 1)
A reaction vessel equipped with a nitrogen introduction tube, a thermometer, and a reflux tube was charged with 22.5 parts by weight of N-vinylpyrrolidone and 127.5 parts by weight of acrylonitrile as monomers, and 150 parts by weight of N-methylpyrrolidone as a reaction solvent. Deoxygenation was performed by blowing. Subsequently, the temperature was raised to 60 ° C., and 0.8 part by weight of an N-methylpyrrolidone solution (concentration: 2% by weight) of 2,2′-azobis (2,4-dimethylvaleronitrile) was added to initiate the reaction. did. 0.4 parts by weight of an N-methylpyrrolidone solution (concentration: 2% by weight) of 2,2′-azobis (2,4-dimethylvaleronitrile) is added every 2 hours after the start of the reaction, and the reaction is performed for a total of 20 hours. It was. The N-methylpyrrolidone solution of the polymer 1 was obtained by adding N-methylpyrrolidone here so that solid content concentration might be 20 weight%.
(製造例2)
反応溶媒として、N−メチルピロリドン120重量部と水30重量部との混合物を用いた以外は実施例1と同様の操作を行い、重合体2のN−メチルピロリドン溶液を得た。
(Production Example 2)
The same operation as in Example 1 was performed except that a mixture of 120 parts by weight of N-methylpyrrolidone and 30 parts by weight of water was used as a reaction solvent, whereby an N-methylpyrrolidone solution of polymer 2 was obtained.
(製造例3)
モノマーとして、N−ビニルピロリドン10重量部およびアクリロニトリル140重量部を用いた以外は実施例1と同様の操作を行い、重合体3のN−メチルピロリドン溶液を得た。
(Production Example 3)
An N-methylpyrrolidone solution of polymer 3 was obtained in the same manner as in Example 1 except that 10 parts by weight of N-vinylpyrrolidone and 140 parts by weight of acrylonitrile were used as monomers.
(製造例4)
モノマーとして、N−ビニルピロリドン12.6重量部、アクリロニトリル120重量部およびアクリル酸−2−ヒドロキシエチル16.5重量部を用いた以外は実施例1と同様の操作を行い、重合体4のN−メチルピロリドン溶液を得た。
(Production Example 4)
The same operation as in Example 1 was carried out except that 12.6 parts by weight of N-vinylpyrrolidone, 120 parts by weight of acrylonitrile and 16.5 parts by weight of 2-hydroxyethyl acrylate were used as monomers. -A methylpyrrolidone solution was obtained.
(製造例5)
モノマーとして、N−ビニルピロリドン20重量部、アクリロニトリル95重量部およびアクリル酸−2−ヒドロキシエチル35重量部を用いた以外は実施例1と同様の操作を行い、重合体5のN−メチルピロリドン溶液を得た。
(Production Example 5)
The same operation as in Example 1 was performed except that 20 parts by weight of N-vinylpyrrolidone, 95 parts by weight of acrylonitrile and 35 parts by weight of 2-hydroxyethyl acrylate were used as monomers, and an N-methylpyrrolidone solution of polymer 5 Got.
(製造例6)
モノマーとして、N−ビニルピロリドン21重量部、アクリロニトリル100重量部およびアクリル酸−n−ブチル29重量部を用いた以外は実施例1と同様の操作を行い、重合体6のN−メチルピロリドン溶液を得た。
(Production Example 6)
The same operation as in Example 1 was carried out except that 21 parts by weight of N-vinylpyrrolidone, 100 parts by weight of acrylonitrile and 29 parts by weight of acrylic acid-n-butyl were used as monomers, and an N-methylpyrrolidone solution of polymer 6 was obtained. Obtained.
(製造例7)
モノマーとして、N−ビニルピロリドン68重量部およびアクリロニトリル82重量部を用いた以外は実施例1と同様の操作を行い、重合体7のN−メチルピロリドン溶液を得た。
(Production Example 7)
An N-methylpyrrolidone solution of polymer 7 was obtained in the same manner as in Example 1 except that 68 parts by weight of N-vinylpyrrolidone and 82 parts by weight of acrylonitrile were used as monomers.
(製造例8)
モノマーとしてアクリロニトリル127.5重量部、反応溶媒としてN−メチルピロリドン175.5重量部を用いた以外は実施例1と同様の操作を行い、重合体8のN−メチルピロリドン溶液を得た。
(Production Example 8)
An N-methylpyrrolidone solution of polymer 8 was obtained in the same manner as in Example 1, except that 127.5 parts by weight of acrylonitrile as a monomer and 175.5 parts by weight of N-methylpyrrolidone as a reaction solvent were used.
(製造例9)
モノマーとしてN−ビニルピロリドン22.5重量部、反応溶媒としてN−メチルピロリドン275.5重量部を用いた以外は実施例1と同様の操作を行い、重合体9のN−メチルピロリドン溶液を得た。
(Production Example 9)
The same operation as in Example 1 was carried out except that 22.5 parts by weight of N-vinylpyrrolidone was used as a monomer and 275.5 parts by weight of N-methylpyrrolidone was used as a reaction solvent, whereby an N-methylpyrrolidone solution of polymer 9 was obtained. It was.
(製造例10)
窒素導入管、温度計、還流管を取り付けた反応容器に、モノマーとして酢酸ビニル22.5重量部およびアクリロニトリル127.5重量部、反応溶媒としてN−メチルピロリドン150重量部を仕込み、窒素吹き込みによる脱酸素を行った。続いて、60℃に昇温し、2,2’−アゾビス(2,4−ジメチルバレロニトリル)のN−メチルピロリドン溶液(濃度:2重量%)0.8重量部を添加して反応を開始した。反応開始後、2時間毎に2,2’−アゾビス(2,4−ジメチルバレロニトリル)のN−メチルピロリドン溶液(濃度:2重量%)0.4重量部を添加し、60℃で合計20時間反応させた。得られた反応溶液に48重量%水酸化ナトリウム水溶液60重量部を添加して3時間反応させることにより酢酸ビニル構造をビニルアルコール構造に変換した。次いで、得られた反応用液を4500重量部の水に添加し、生成した沈殿物を取り出し、これを固形分濃度が20重量%となる量のN−メチルピロリドンに溶解することにより重合体10のN−メチルピロリドン溶液を得た。
(Production Example 10)
A reaction vessel equipped with a nitrogen introduction tube, a thermometer, and a reflux tube was charged with 22.5 parts by weight of vinyl acetate and 127.5 parts by weight of acrylonitrile as monomers, and 150 parts by weight of N-methylpyrrolidone as a reaction solvent. Oxygen was done. Subsequently, the temperature was raised to 60 ° C., and 0.8 part by weight of an N-methylpyrrolidone solution (concentration: 2% by weight) of 2,2′-azobis (2,4-dimethylvaleronitrile) was added to initiate the reaction. did. 0.4 parts by weight of an N-methylpyrrolidone solution (concentration: 2% by weight) of 2,2′-azobis (2,4-dimethylvaleronitrile) is added every 2 hours after the start of the reaction, and a total of 20 at 60 ° C. Reacted for hours. A vinyl acetate structure was converted to a vinyl alcohol structure by adding 60 parts by weight of a 48 wt% aqueous sodium hydroxide solution to the resulting reaction solution and reacting for 3 hours. Subsequently, the obtained reaction solution was added to 4500 parts by weight of water, the produced precipitate was taken out, and dissolved in N-methylpyrrolidone in an amount such that the solid content concentration was 20% by weight. Of N-methylpyrrolidone was obtained.
(製造例11)
モノマーとして、N−ビニルピロリドン10重量部および酢酸ビニル140重量部を用いた以外は実施例1と同様の操作を行い、重合体11のN−メチルピロリドン溶液を得た。
(Production Example 11)
An N-methylpyrrolidone solution of polymer 11 was obtained in the same manner as in Example 1 except that 10 parts by weight of N-vinylpyrrolidone and 140 parts by weight of vinyl acetate were used as monomers.
<重合体の重量平均分子量>
製造例1〜11で得られた重合体の重量平均分子量を、GPC−MALLS法で測定した。なお、測定条件は以下の通りである。
(測定条件)
カラム:PLgel 5μm Mixed−C(7.5mmφ×300mm×2本;Polymer Laboratories社製)
移動相:リチウムクロライド(50mM)のジメチルホルムアミド溶液、流量:0.5mL/min
カラム温度:50℃
検出器:示差屈折計(昭和電工(株)製 RI−71)、多角度光散乱検出器(Wyatt Technology社製 DAWN EOS)。
<Weight average molecular weight of polymer>
The weight average molecular weight of the polymers obtained in Production Examples 1 to 11 was measured by the GPC-MALLS method. Measurement conditions are as follows.
(Measurement condition)
Column: PLgel 5 μm Mixed-C (7.5 mmφ × 300 mm × 2; manufactured by Polymer Laboratories)
Mobile phase: dimethylformamide solution of lithium chloride (50 mM), flow rate: 0.5 mL / min
Column temperature: 50 ° C
Detector: differential refractometer (RI-71 manufactured by Showa Denko KK), multi-angle light scattering detector (DAWN EOS manufactured by Wyatt Technology).
<構成モノマーの組成>
製造例1〜7、10および11で得られた重合体のN−メチルピロリドン溶液から、N−メチルピロリドン溶液を減圧留去することにより乾燥し、さらにジメチルスルホキシド−d6に溶解した。この溶液の用いて13C−NMR(装置名:Bruker社製AV400M、定量モード)を測定し、以下に示す各モノマー由来のピークの面積比から共重合体中のモノマー構成比率(モル%)を算出した。
[各モノマー由来のピークのケミカルシフト]
アクリロニトリル:120ppm付近
N−ビニルピロリドン:31ppm付近
アクリル酸2−ヒドロキシエチル:59ppm付近
アクリル酸n−ブチル:19ppm付近
ビニルアルコール:60−70ppm付近
酢酸ビニル:23ppm付近
<Composition of constituent monomer>
From the N-methylpyrrolidone solutions of the polymers obtained in Production Examples 1 to 7, 10 and 11, the N-methylpyrrolidone solution was dried by distillation under reduced pressure, and further dissolved in dimethyl sulfoxide-d6. Using this solution, 13 C-NMR (apparatus name: AV400M manufactured by Bruker, quantitative mode) was measured, and the monomer composition ratio (mol%) in the copolymer was determined from the area ratio of the peaks derived from each monomer shown below. Calculated.
[Chemical shift of peak derived from each monomer]
Acrylonitrile: around 120 ppm N-vinylpyrrolidone: around 31 ppm 2-hydroxyethyl acrylate: around 59 ppm n-butyl acrylate: around 19 ppm vinyl alcohol: around 60-70 ppm vinyl acetate: around 23 ppm
(実施例1〜6、比較例1〜5)
表2に記載の重合体の20重量%N−メチルピロリドン溶液32重量部(分散剤である各重合体6.4重量部および非水系液体であるN−メチルピロリドン25.6重量部の混合物)とカーボンブラック(商品名:Super−P、Timcal社製)12gとをフィルミックス(プライミクス社製)を用いて攪拌することにより炭素材料分散体を得た。得られた炭素材料分散体を用いて、分散性および耐溶媒性の評価を下記の方法で行った。結果を表2に示す。なお、比較例2および4は分散できなかったため、経時分散性および耐溶媒性の評価を行わなかった。
(Examples 1-6, Comparative Examples 1-5)
32 parts by weight of a 20% by weight N-methylpyrrolidone solution of the polymer shown in Table 2 (mixture of 6.4 parts by weight of each polymer as a dispersant and 25.6 parts by weight of N-methylpyrrolidone as a non-aqueous liquid) And carbon black (trade name: Super-P, manufactured by Timcal) (12 g) were stirred using a film mix (manufactured by Primex) to obtain a carbon material dispersion. Using the obtained carbon material dispersion, dispersibility and solvent resistance were evaluated by the following methods. The results are shown in Table 2. Since Comparative Examples 2 and 4 could not be dispersed, evaluation of dispersibility with time and solvent resistance was not performed.
<評価方法>
(1)初期分散性
攪拌終了後の分散体を目視にて観察し、下記の基準で評価した。
○:底部に沈殿が見られない。
×:底部に沈殿が見られる。
<Evaluation method>
(1) Initial dispersibility The dispersion after stirring was visually observed and evaluated according to the following criteria.
○: No precipitation is observed at the bottom.
X: Precipitation is seen at the bottom.
(2)経時分散性
攪拌終了後、25℃で2週間静置したあとの分散体を目視にて観察し、下記の基準で評価した。
○:底部に沈殿が見られない。
×:底部に沈殿が見られる。
(2) Dispersibility with time After completion of stirring, the dispersion after standing at 25 ° C. for 2 weeks was visually observed and evaluated according to the following criteria.
○: No precipitation is observed at the bottom.
X: Precipitation is seen at the bottom.
(3)耐溶媒性
炭素材料分散体を膜厚100μmとなるように塗工機を用いてアルミ箔上に塗布し、130℃で乾燥することにより塗膜(乾燥物)を得た。続いて、25℃の溶媒(水、エタノールまたはエチレンカーボネート)に1時間浸漬し、浸漬後の塗膜を目視にて観察し、下記の基準で評価した。
○:塗膜の溶出が見られない。
×:塗膜の溶出が見られる。
(3) Solvent resistance
The carbon material dispersion was applied onto an aluminum foil using a coating machine so as to have a film thickness of 100 μm, and dried at 130 ° C. to obtain a coating film (dried product). Subsequently, the film was immersed in a solvent at 25 ° C. (water, ethanol or ethylene carbonate) for 1 hour, and the coated film after immersion was visually observed and evaluated according to the following criteria.
○: Elution of the coating film is not observed.
X: Elution of the coating film is observed.
表2から明らかなように、本発明の分散剤は、分散性に優れるとともに、これを用いて得られる乾燥物の耐溶媒性が優れることがわかる。一方、比較例1では、構成モノマーにおけるN−ビニルピロリドン(B)の割合が大きいため、有機溶媒に対する耐溶媒性が劣っている。また、比較例4では、N−ビニルピロリドン(B)に代えてビニルアルコールを用いたため分散性が得られなかった。さらに、比較例5では、アクリロニトリル(A)に代えて酢酸ビニルを用いたため、有機溶媒に対する耐溶媒性が劣っている。 As is apparent from Table 2, it can be seen that the dispersant of the present invention is excellent in dispersibility and the solvent resistance of a dried product obtained using the dispersant. On the other hand, in Comparative Example 1, since the ratio of N-vinylpyrrolidone (B) in the constituent monomer is large, the solvent resistance against the organic solvent is inferior. In Comparative Example 4, dispersibility was not obtained because vinyl alcohol was used instead of N-vinylpyrrolidone (B). Furthermore, in Comparative Example 5, since vinyl acetate was used instead of acrylonitrile (A), the solvent resistance against the organic solvent was poor.
本発明の分散剤は、炭素材料などの分散剤として利用可能である。また、本発明の分散体は、塗料、インキ、筆記具、化粧料、電池、電極など、炭素材料を使用する用途に利用可能である。 The dispersant of the present invention can be used as a dispersant for carbon materials and the like. In addition, the dispersion of the present invention can be used for applications using carbon materials such as paints, inks, writing instruments, cosmetics, batteries, and electrodes.
Claims (6)
前記構成モノマーにおけるアクリロニトリル(A)の割合が50〜99モル%であり、N−ビニルピロリドン(B)の割合が1〜30モル%である炭素材料用分散剤。 A carbon material dispersant containing a copolymer containing at least acrylonitrile (A) and N-vinylpyrrolidone (B) as constituent monomers,
The dispersing agent for carbon materials whose ratio of acrylonitrile (A) in the said structural monomer is 50-99 mol%, and whose ratio of N-vinylpyrrolidone (B) is 1-30 mol%.
A carbon material-containing solid obtained by drying a composition containing the dispersion according to claim 5.
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