JP7418181B2 - 分散剤とそれを用いた分散液 - Google Patents
分散剤とそれを用いた分散液 Download PDFInfo
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- JP7418181B2 JP7418181B2 JP2019201739A JP2019201739A JP7418181B2 JP 7418181 B2 JP7418181 B2 JP 7418181B2 JP 2019201739 A JP2019201739 A JP 2019201739A JP 2019201739 A JP2019201739 A JP 2019201739A JP 7418181 B2 JP7418181 B2 JP 7418181B2
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- meth
- carbon atoms
- fine particles
- oxide
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- 239000006185 dispersion Substances 0.000 title claims description 65
- 239000002270 dispersing agent Substances 0.000 title claims description 58
- 239000010419 fine particle Substances 0.000 claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 150000001768 cations Chemical class 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 18
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 13
- 239000003125 aqueous solvent Substances 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical class O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 claims 1
- -1 polyoxyethylene Polymers 0.000 description 119
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 75
- 150000001875 compounds Chemical class 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 150000002500 ions Chemical class 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 235000001014 amino acid Nutrition 0.000 description 22
- 239000002612 dispersion medium Substances 0.000 description 20
- 150000001413 amino acids Chemical class 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000000178 monomer Substances 0.000 description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 10
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 229910001849 group 12 element Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 230000007704 transition Effects 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 229910001413 alkali metal ion Inorganic materials 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 238000010701 ester synthesis reaction Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 5
- 229910001449 indium ion Inorganic materials 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910001432 tin ion Inorganic materials 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- JJUBFBTUBACDHW-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JJUBFBTUBACDHW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000012644 addition polymerization Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 4
- 239000010696 ester oil Substances 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 229920000205 poly(isobutyl methacrylate) Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910001414 potassium ion Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910001415 sodium ion Inorganic materials 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
- 239000001856 Ethyl cellulose Substances 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 235000019325 ethyl cellulose Nutrition 0.000 description 3
- 229920001249 ethyl cellulose Polymers 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- SDTORDSXCYSNTD-UHFFFAOYSA-N 1-methoxy-4-[(4-methoxyphenyl)methoxymethyl]benzene Chemical group C1=CC(OC)=CC=C1COCC1=CC=C(OC)C=C1 SDTORDSXCYSNTD-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- GNULGOSSPWDTMD-UHFFFAOYSA-N NC(=O)OCC.C(CCCCCN=C=O)N=C=O.C(C=C)(=O)OCC(COC(C=C)=O)(COC(C=C)=O)CO Chemical compound NC(=O)OCC.C(CCCCCN=C=O)N=C=O.C(C=C)(=O)OCC(COC(C=C)=O)(COC(C=C)=O)CO GNULGOSSPWDTMD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
- 229910003452 thorium oxide Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
下記式(I):
(1)XとYのいずれもが-O-SO3M1(M1は水素イオン又は塩となる対カチオンを示す。)
(2)XとYのいずれか一方が-O-(AO)pHであり他方が-O-(AO)qH(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
(3)XとYのいずれか一方が-O-(AO)pSO3M1(M1は水素イオン又は塩となる対カチオンを示す。)であり他方が-O-(AO)qSO3M1(M1は水素イオン又は塩となる対カチオンを示す。)(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
(4)XとYのいずれもが-OC(=O)-CH2CH2C(=O)OM2(M2は水素イオン又は塩となる対カチオンを示す。)
(5)XとYのいずれか一方が-O-(AO)pC(=O)-CH2CH2C(=O)OM2(M2は水素イオン又は塩となる対カチオンを示す。)であり他方が-O-(AO)qC(=O)-CH2CH2C(=O)OM2(M2は水素イオン又は塩となる対カチオンを示す。)(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
(6)XとYのいずれもが-OC(=O)-Bz-(C(=O)OM2)2(Bzは、ベンゼン環を示し、M2は水素イオン又は塩となる対カチオンを示す。)、
(7)XとYのいずれか一方が-O-(AO)pC(=O)-Bz-(C(=O)OM2)2(Bzは、ベンゼン環を示し、M2は水素イオン又は塩となる対カチオンを示す。)であり他方が-O-(AO)qC(=O)-Bz-(C(=O)OM2)2(Bzは、ベンゼン環を示し、M2は水素イオン又は塩となる対カチオンを示す。)(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
(8)XとYのいずれか一方が-OPO3M3であり(M3は水素イオン又は塩となる対カチオンを示す。)他方が水酸基
(9)XとYのいずれもが-OPO3M3(M3は水素イオン又は塩となる対カチオンを示す。)
(10)XとYのいずれか一方が-O-(AO)pPO3M3(M1は水素イオン又は塩となる対カチオンを示す。)であり他方が-O-(AO)qPO3M3(M1は水素イオン又は塩となる対カチオンを示す。)(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
(11)XとYのいずれか一方が-NR4R5R6+A-であり(R4、R5はそれぞれ独立にメチル基、エチル基、又はヒドロキシエチル基を示し、R6はメチル基、エチル基、又はジヒドロキシプロピル基を示し、Aはハロゲンを示す。)他方が水酸基
(12)XとYのいずれもが-OC(=O)-CHR7-NR8R9(R7は水素原子、炭素数1~4のアルキル基、炭素数1~4のアルキルチオアルキル基、炭素数1~3のアルキル基にチオール基が結合したチオール含有アルキル基、フェニル基、炭素数1~3で1級もしくは2級ヒドロキシ基を有するヒドロキシアルキル基、又はヒドロキシフェニル基を示す。R8及びR9はそれぞれ独立に水素原子、メチル基、又はエチル基を示す。)
(13)XとYのいずれか一方が-O-(AO)pC(=O)-CHR7-NR8R9(R7は水素原子、炭素数1~4のアルキル基、炭素数1~4のアルキルチオアルキル基、炭素数1~3のアルキル基にチオール基が結合したチオール含有アルキル基、フェニル基、炭素数1~3で1級もしくは2級ヒドロキシ基を有するヒドロキシアルキル基、又はヒドロキシフェニル基を示す。R8及びR9はそれぞれ独立に水素原子、メチル基、又はエチル基を示す。)であり他方が-O-(AO)qC(=O)-CHR7-NR8R9(R7は水素原子、炭素数1~4のアルキル基、炭素数1~4のアルキルチオアルキル基、炭素数1~3のアルキル基にチオール基が結合したチオール含有アルキル基、フェニル基、炭素数1~3で1級もしくは2級ヒドロキシ基を有するヒドロキシアルキル基、又はヒドロキシフェニル基を示す。R8及びR9はそれぞれ独立に水素原子、メチル基、又はエチル基を示す。)(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
Zは-O-C(=O)-、-C(=O)-O-、-NH-C(=O)-、又は-O-を示す。)で表わされる。
実施例1:以下の構造を有するジェミニ型界面活性剤を使用した。
比較例2:以下の構造を有するジェミニ型界面活性剤;ジェミサーフ α142(中京油脂株式会社)を使用した。
分散媒として、有機溶媒として、トルエン、トルエン/エタノール、酢酸エチル、メチルエチルケトン、2-プロパノール、ポリマー溶液として、ポリメタクリル酸メチル/THF、ポリメタクリル酸イソブチル(東京化成試薬)/トルエン、ポリメタクリル酸イソブチル(東京化成試薬)/メンタノールアセテート、ポリメタクリル酸イソブチル(東京化成試薬)/酢酸エチル、ポリメタクリル酸イソブチル(東京化成試薬)/トルエン/エタノール、オリゴウレタンアクリレートUF-8001G(共栄社化学製)/トルエン、オリゴウレタンアクリレート(UF-8001G、共栄社化学製)/トルエン、オリゴウレタンアクリレート(UF-8001G、共栄社化学製)/メンタノールアセテート(日本香料薬品製)、オリゴウレタンアクリレート(UF-8001G、共栄社化学製)/IB-XA(共栄社化学製)、オリゴウレタンアクリレート(UF-8001G、共栄社化学製)/トルエン/エタノール、ウレタンアクリレート(UA-306H、共栄社化学製)/IB-XA(共栄社化学製)、ポリビニルブチラール(エスレックBM-2、積水化学工業製)/ターピネオール(日本香料薬品製)、ポリビニルブチラール(エスレックBM-2、積水化学工業製)/酢酸エチル、ポリビニルブチラール(エスレックBL-2H、積水化学工業製)/トルエン/エタノール、エチルセルロース(約49%エトキシ)100(富士フイルム和光純薬工業製/トルエン、エチルセルロース(約49%エトキシ)100(富士フイルム和光純薬工業製/メンタノールアセテート、エチルセルロース(約49%エトキシ)100(富士フイルム和光純薬工業製/トルエン/エタノール、エステル油としては、パルミチン酸イソプロピル(東京化成試薬)、オレイン酸ネオペンチルグリコールエステル(ミヨシ油脂製、ONPG-200)、セバシン酸ジエチル(東京化成試薬)のいずれかを使用した。
上記の分散媒中に分散剤を溶解し、分散質(微粒子)を添加、高濃度(対微粒子濃度5%、微粒子濃度33~70%)では自転公転ミキサー(10分,2000rpm)、低濃度(対微粒子濃度5~10%、微粒子濃度1~10%)は超音波洗浄機(3分)又は薄膜旋回型ミキサー(周速40m/s、5分)で分散を行って、分散液を得た。表1~16記載の充填率は、分散液中の分散質の質量%を示す。
実施例1~4及び比較例1~5の分散剤の効果について、分散液の溶解性、分散性、濡れ性、分散安定性、粘性を以下の基準に従って評価した。
(1)分散性
光学顕微鏡写真(倍率1000倍)から、微粒子の分散性を目視にて以下の基準で評価した。
評価基準
◎:均一に分散して、凝集していない。
○:ほとんど分散しているが、僅かに凝集物が見られる
△:分散はしているが、凝集物が多い。
×:ほとんど凝集している
(2)溶解性
評価基準
◎:完全に溶解している
○:僅かに溶け残りがある
△:うっすら白濁し、分散剤が分散している。
×:全く溶解しない
(3)濡れ性
顕微鏡観察時にガラス基板への濡れ性を外観と顕微鏡画像より以下の基準で評価した。
評価基準
◎:目視で、ガラス基板に対して完全に均一な状態を保っており、相分離が見られない。
○:ほとんど均一で相分離が見られない
△:一部凝集しており、相分離が見られる。
×:凝集塊が多く、殆ど相分離している。
(4)分散安定性(目視)
25℃の恒温槽で保管した分散液を1週間後に観察した。
評価基準
◎:分散直後の状態と比べて粒子の沈降が見られない。
○:分散直後の状態と比べて、クリアな相がなく、濃度勾配がある。
△:分散直後の状態と比べて半分以上がクリアな相となっている。
×:分散直後の状態と比べてほとんど沈降している。
(5)粘性
低濃度(目視)
◎:分散媒と比べて殆ど粘性が変わらない。
○:分散媒と比べて僅かに粘性がある。
△:分散媒と比べて粘性がある。
×:分散媒と比べてかなり粘性がある。
高濃度(粘度測定)
動的粘弾性装置(Paar Physica MCR-300)を用いて温度20℃、せん断速度0.1~100(1/s)で測定を行い、評価を行った。粘度は、せん断速度約1(1/s)の場合の粘度にて評価した。
評価基準
◎:0.01Pa・s以上~5Pa・s未満
○:5Pa・s以上~20Pa・s未満
△:20Pa・s以上~100Pa・s未満
×:100Pa・s以上
(6)総合評価
ハンドリング性について以下の基準で総合評価を行った。
評価基準
○:上記(1)~(5)より全体的にハンドリング性良好
△:上記(1)~(5)より全体的にハンドリング性低い
×:上記(1)~(5)より全体的にハンドリング性非常に低い
上記の評価結果を表1~表16に示す。
Claims (3)
- 無機微粒子である金属酸化物、水酸化物およびチタン酸化合物のうちの少なくともいずれかを非水系溶媒中に分散させるための分散剤であって、
下記式(I):
X及びYは、次の(2)、(4)、(8)、(9)、(10)のいずれかである。
(2)XとYのいずれか一方が-O-(AO)pHであり他方が-O-(AO)qH(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
(4)XとYのいずれもが-OC(=O)-CH2CH2C(=O)OM2(M2は水素イオン又は塩となる対カチオンを示す。)
(8)XとYのいずれか一方が-OPO3M3であり(M3は水素イオン又は塩となる対カチオンを示す。)他方が水酸基
(9)XとYのいずれもが-OPO3M3(M3は水素イオン又は塩となる対カチオンを示す。)
(10)XとYのいずれか一方が-O-(AO)pPO3M3(M1は水素イオン又は塩となる対カチオンを示す。)であり他方が-O-(AO)qPO3M3(M1は水素イオン又は塩となる対カチオンを示す。)(AOは炭素数2~3のアルキレンオキシドより誘導されるオキシアルキレン基を示し、pは0~100の整数、qは0~100の整数を示し、pとqとの和は1~200である。)
Zは-O-C(=O)-、-C(=O)-O-、-NH-C(=O)-、又は-O-を示す。)で表わされる、分散剤。 - 非水系溶媒が反応性溶媒である、請求項1に記載の分散剤。
- 請求項1または2に記載の分散剤と無機微粒子とを含有する、分散液。
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JP2011190184A (ja) | 2010-03-11 | 2011-09-29 | Miyoshi Oil & Fat Co Ltd | 新規ジカルボン酸型化合物 |
JP2011236347A (ja) | 2010-05-11 | 2011-11-24 | Miyoshi Oil & Fat Co Ltd | ノニオン型界面活性剤 |
JP2014037355A (ja) | 2012-08-10 | 2014-02-27 | Miyoshi Oil & Fat Co Ltd | 新規フッ化炭素鎖含有化合物とその製造方法ならびに用途 |
JP2014129302A (ja) | 2012-12-28 | 2014-07-10 | Miyoshi Oil & Fat Co Ltd | 新規ジェミニ型化合物とその製造方法およびそれを用いたカチオン性界面活性剤、分散剤 |
JP2015000396A (ja) | 2013-06-18 | 2015-01-05 | 第一工業製薬株式会社 | 非水性分散媒用分散剤 |
JP2015178102A (ja) | 2014-02-28 | 2015-10-08 | ミヨシ油脂株式会社 | ジェミニ型界面活性剤を分散剤として用いたナノカーボン物質の水性分散液及びその製造方法 |
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JP2011190184A (ja) | 2010-03-11 | 2011-09-29 | Miyoshi Oil & Fat Co Ltd | 新規ジカルボン酸型化合物 |
JP2011236347A (ja) | 2010-05-11 | 2011-11-24 | Miyoshi Oil & Fat Co Ltd | ノニオン型界面活性剤 |
JP2014037355A (ja) | 2012-08-10 | 2014-02-27 | Miyoshi Oil & Fat Co Ltd | 新規フッ化炭素鎖含有化合物とその製造方法ならびに用途 |
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