JP5105693B2 - 水性顔料分散体及び水性顔料記録液 - Google Patents
水性顔料分散体及び水性顔料記録液 Download PDFInfo
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- JP5105693B2 JP5105693B2 JP2003318236A JP2003318236A JP5105693B2 JP 5105693 B2 JP5105693 B2 JP 5105693B2 JP 2003318236 A JP2003318236 A JP 2003318236A JP 2003318236 A JP2003318236 A JP 2003318236A JP 5105693 B2 JP5105693 B2 JP 5105693B2
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- pigment
- aqueous pigment
- aqueous
- organic polymer
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- 239000000049 pigment Substances 0.000 title claims description 170
- 239000006185 dispersion Substances 0.000 title claims description 108
- 239000007788 liquid Substances 0.000 title claims description 55
- 239000001052 yellow pigment Substances 0.000 claims description 124
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 85
- 125000000129 anionic group Chemical group 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 73
- 229920000620 organic polymer Polymers 0.000 claims description 68
- -1 ammonium ions Chemical class 0.000 claims description 45
- 239000002245 particle Substances 0.000 claims description 35
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 239000011246 composite particle Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000007942 carboxylates Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
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- 230000009477 glass transition Effects 0.000 claims description 4
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
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- 238000000034 method Methods 0.000 description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000012736 aqueous medium Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- 239000002585 base Substances 0.000 description 14
- 239000000178 monomer Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 125000000542 sulfonic acid group Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
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- 229910052708 sodium Inorganic materials 0.000 description 7
- 125000004436 sodium atom Chemical group 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920001214 Polysorbate 60 Polymers 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 5
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
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- 238000003916 acid precipitation Methods 0.000 description 5
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- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
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- 239000011259 mixed solution Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
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- 239000000975 dye Substances 0.000 description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- UXDCSXDWLVYCQF-UHFFFAOYSA-N (3-methyloxiran-2-yl)methyl 2-methylprop-2-enoate Chemical compound CC1OC1COC(=O)C(C)=C UXDCSXDWLVYCQF-UHFFFAOYSA-N 0.000 description 2
- LSLTZMYFLMDGHR-UHFFFAOYSA-N (3-methyloxiran-2-yl)methyl prop-2-enoate Chemical compound CC1OC1COC(=O)C=C LSLTZMYFLMDGHR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- UVSVPOYEURWBLA-UHFFFAOYSA-N 1-methoxy-1-[2-(1-methoxyethoxy)ethoxy]ethane Chemical compound COC(C)OCCOC(C)OC UVSVPOYEURWBLA-UHFFFAOYSA-N 0.000 description 2
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- QGVQVNIIRBPOAM-UHFFFAOYSA-N dodecyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)OCCCCCCCCCCCC)=CC=CC2=C1 QGVQVNIIRBPOAM-UHFFFAOYSA-N 0.000 description 1
- JZKFHQMONDVVNF-UHFFFAOYSA-N dodecyl sulfate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCOS(O)(=O)=O JZKFHQMONDVVNF-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 125000003700 epoxy group Chemical group 0.000 description 1
- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011976 maleic acid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
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- 239000001923 methylcellulose Substances 0.000 description 1
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- RFZRLVGQBIINKQ-UHFFFAOYSA-N n-(2-aminoethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCN RFZRLVGQBIINKQ-UHFFFAOYSA-N 0.000 description 1
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- HXJGFDIZSMWOGY-UHFFFAOYSA-N n-(2-azaniumylethyl)prop-2-enimidate Chemical compound NCCNC(=O)C=C HXJGFDIZSMWOGY-UHFFFAOYSA-N 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
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- FZLUWDXMHJPGBS-UHFFFAOYSA-N n-(3-aminopropyl)prop-2-enamide Chemical compound NCCCNC(=O)C=C FZLUWDXMHJPGBS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- DCBBWYIVFRLKCD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CN(C)CCNC(=O)C(C)=C DCBBWYIVFRLKCD-UHFFFAOYSA-N 0.000 description 1
- WDQKICIMIPUDBL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]prop-2-enamide Chemical compound CN(C)CCNC(=O)C=C WDQKICIMIPUDBL-UHFFFAOYSA-N 0.000 description 1
- YPQZNZMMEBHDSC-UHFFFAOYSA-N n-[2-(dimethylamino)propyl]-2-methylprop-2-enamide Chemical compound CN(C)C(C)CNC(=O)C(C)=C YPQZNZMMEBHDSC-UHFFFAOYSA-N 0.000 description 1
- SLGDEOFMEQZRLN-UHFFFAOYSA-N n-[2-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)C(C)CNC(=O)C=C SLGDEOFMEQZRLN-UHFFFAOYSA-N 0.000 description 1
- FZGONJFXUHURTC-UHFFFAOYSA-N n-[2-(methylamino)ethyl]prop-2-enamide Chemical compound CNCCNC(=O)C=C FZGONJFXUHURTC-UHFFFAOYSA-N 0.000 description 1
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- FYBCLPJRKYVSJG-UHFFFAOYSA-N n-[3-(methylamino)propyl]prop-2-enamide Chemical compound CNCCCNC(=O)C=C FYBCLPJRKYVSJG-UHFFFAOYSA-N 0.000 description 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 description 1
- UVFBKBLAXUEHEY-UHFFFAOYSA-N n-ethylprop-2-enamide;n-propylprop-2-enamide Chemical compound CCNC(=O)C=C.CCCNC(=O)C=C UVFBKBLAXUEHEY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- KIHUPOKUSVEICJ-UHFFFAOYSA-N nonyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KIHUPOKUSVEICJ-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- MXXDSLLVYZMTFA-UHFFFAOYSA-N octadecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 MXXDSLLVYZMTFA-UHFFFAOYSA-N 0.000 description 1
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DQVOTEHORLHPRW-UHFFFAOYSA-N prop-2-enyl decanoate Chemical compound CCCCCCCCCC(=O)OCC=C DQVOTEHORLHPRW-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N sec-pentyl alcohol Natural products CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- JSMHQMIPUOPQLR-UHFFFAOYSA-M sodium;dioctadecyl phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOP([O-])(=O)OCCCCCCCCCCCCCCCCCC JSMHQMIPUOPQLR-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- UWNNZXDNLPNGQJ-UHFFFAOYSA-N tert-butyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(C)(C)C UWNNZXDNLPNGQJ-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
Description
また本発明は、この様な水性顔料記録液を容易に調製し得る水性顔料分散体を提供することを目的とする。
攪拌装置、滴下装置、温度センサー、および上部に窒素導入装置を有する環流装置を取り付けた反応容器を有する自動重合反応装置(重合試験機DSL−2AS型、轟産業(株)製)の反応容器にメチルエチルケトン1,100部を仕込み、攪拌しながら反応容器内を窒素置換した。反応容器内を窒素雰囲気に保ちながら80℃に昇温させた後、滴下装置よりメタクリル酸2−ヒドロキシエチル75.0部、メタアクリル酸138.0部、スチレン200.0部、メタクリル酸ベンジル300.0部、メタアクリル酸ブチル262部、アクリル酸ブチル25部および「パーブチル O」(有効成分ペルオキシ2−エチルヘキサン酸t−ブチル、日本油脂(株)製)80.0部の混合液を4時間かけて滴下した。滴下終了後、さらに同温度で15時間反応を継続させて、酸価90、重量平均分子量21,500、ガラス転移点(計算値)34℃のアニオン性基含有有機高分子化合物溶液を得た。反応終了後、メチルエチルケトンの一部を減圧留去し、樹脂溶液の不揮発分を50%に調整した。
(ジアゾ化液の合成)
水700部と、35%塩酸315部の混合液に4−ニトロ−o−アニシジン181.4部と下記化合物1の68.8部を加えて攪拌し、氷600部を加えて冷却後、46.8%亜硝酸ソーダ水溶液188部を加え、10℃以下で1時間攪拌し、スルファミン酸で過剰の亜硝酸を消失させた後、ろ過してジアゾ化液とした。
酢酸ソーダ100部を水8900部に溶解した後、アセトアセチル−o−アニシダイド256.7部を加え、さらに30%苛性ソーダ185部を加えて溶解させ、80%酢酸を滴下してpH6に調整してカップラー液とした。
上記カップラー液にジアゾ化液を25℃で滴下して反応させた後90℃で30分熟成させた。更にろ過、水洗、乾燥、粉砕して黄色顔料組成物(B−1)495部を得た。
4−ニトロ−o−アニシジンの添加量を185.5部とし、上記化合物1の68.8部の代わりに下記化合物2の45.3部を用いた以外は合成例2と同様にして黄色顔料組成物(B−2)472部を得た。
(ジアゾ化液の合成)
水700部と、35%塩酸315部の混合液に4−ニトロ−o−アニシジン197.6部と3,3′−ジメチル−4,4′−ジアミノビフェニル−6,6′−ジスルホン酸8.9部を加えて攪拌し、氷600部を加えて冷却後、46.8%亜硝酸ソーダ水溶液188部を加え、10℃以下で1時間攪拌し、スルファミン酸で過剰の亜硝酸を消失させた後、ろ過してジアゾ化液とした。
酢酸ソーダ100部を水8900部に溶解した後、アセトアセチル−o−アニシダイド256.7部を加え、さらに30%苛性ソーダ185部を加えて溶解させ、80%酢酸を滴下してpH6に調整してカップラー液とした。
水400部と35%塩酸58.4部の混合溶液中に、下記化合物3の83.2部を加えて攪拌し、氷500部を加えて冷却後、46.8%亜硝酸ソーダ水溶液26部を加え、10℃以下で1時間攪拌し、スルファミン酸で過剰の亜硝酸を消失させた後、ろ過してジアゾ化液とした。
上記カップラー液にジアゾ化液を25℃で滴下して反応させた後、上記配合剤ペースト264部を添加し、攪拌しながら80℃で30分熟成させた。更にろ過、水洗、乾燥、粉砕して黄色顔料組成物(B−3)545部を得た。
化合物1の68.8部の代わりにp−トルイジン−m−スルホン酸22.4部を用いた以外は合成例2と同様にして黄色顔料組成物(B−4)446部を得た。
4−ニトロ−o−アニシジンの添加量を201.6部とし、化合物1の添加を省略した以外は合成例2と同様にして黄色顔料組成物(B−5)458部を得た。
化合物1の68.8部に代えて上記化合物3の62.4部を用いる以外は合成例2と同様にして、黄色顔料組成物(B−6)482部を得た。
冷却用ジャケットを備えた混合槽に、合成例2で合成した黄色顔料組成物(B−1)1000部と、ジョンクリル61J(ジョンソンポリマー社製 酸価195)200部、20%水酸化ナトリウム水溶液139部、および水2861部、を仕込み、攪拌、混合した。混合液を直径0.3mmのジルコニアビーズを充填した分散装置(SCミル SC100/32型、三井鉱山(株)製)に通し、循環方式(分散装置より出た分散液を混合槽に戻す方式)により6時間分散した。分散装置の回転数は2,700回転/分とし、冷却用ジャケットには冷水を通して分散液温度が40℃以下に保たれるようにした。
合成例2で合成した黄色顔料組成物(B−1)1000部の代わりに合成例5で合成した黄色顔料組成物(B−4)1000部を用いた以外は比較例1と同様にして不揮発分20%の、モノアゾ黄色主顔料(1)と、一般式(2)及び(3)に該当しないナトリウム原子で中和されたスルホン酸基を有するモノアゾ黄色顔料とナトリウム原子で中和されたカルボキシル基含有有機高分子化合物とが独立して水性媒体中に分散した水性顔料分散体を得た。
合成例2で合成した黄色顔料組成物(B−1)1000部の代わりに合成例5で合成した黄色顔料組成物(B−4)1000部を用いた以外は実施例1と同様にして不揮発分20%の、モノアゾ黄色主顔料(1)と一般式(2)及び(3)に該当しないナトリウム原子で中和されたスルホン酸基を有するモノアゾ黄色顔料(3)とがナトリウム原子で中和されたカルボキシル基含有有機高分子化合物で被覆された複合粒子として水性媒体中に分散した水性顔料分散体を得た。
合成例2で合成した黄色顔料組成物(B−1)1000部の代わりに合成例6で合成した黄色顔料組成物(B−5)1000部を用いた以外は実施例1と同様にして不揮発分20%の、モノアゾ黄色主顔料(1)がナトリウム原子で中和されたカルボキシル基含有有機高分子化合物で被覆された複合粒子として水性媒体中に分散した水性顔料分散体を得た。
合成例2で合成した黄色顔料組成物(B−1)1000部の代わりに合成例6で合成した黄色顔料組成物(B−5)1000部を用い、20%水酸化カリウム水溶液80部の代わりにモノエタノールアミン20部を用いた以外は実施例1と同様にして不揮発分20%の、モノアゾ黄色主顔料(1)がモノエタノールアミンで中和されたカルボキシル基含有有機高分子化合物で被覆された複合粒子として水性媒体中に分散した水性顔料分散体を得た。
特開平7−228808号公報記載の実施例1を参考にしてピエゾ方式インクジェット記録用水性インクを調製した。インク組成を以下に示す。
トリエチレングリコールモノブチルエーテル 10.0部
ジエチレングリコール 15.0部
サーフィノール465(エアフ゜ロタ゛クツ社製) 0.8部
水 49.2部
Claims (8)
- 下記一般式(1)で表されるモノアゾ黄色主顔料と、下記一般式(2)で示されるジスアゾ黄色顔料またはその塩、及び/または、下記一般式(3)で示されるモノアゾ黄色顔料またはその塩と、アニオン性基含有有機高分子化合物とを含み、分散粒子が平均粒子径200nm以下に微分散されている水性顔料記録液用水性顔料分散体において、分散粒子が、下記一般式(1)で表されるモノアゾ黄色主顔料と、下記一般式(2)で示されるジスアゾ黄色顔料またはその塩及び/または下記一般式(3)で示されるモノアゾ黄色顔料またはその塩とが、いずれも中和されたアニオン性基含有有機高分子化合物で被覆されている複合粒子であることを特徴とする水性顔料記録液用水性顔料分散体。
〔上記一般式(1)〜(3)に於いて、R1及びR2は互いに相違する水素原子、塩素原子、ニトロ基、メチル基又はメトキシ基を表し、R3、R4及びR5は同じかまたは相違する水素原子、塩素原子、メチル基、メトキシ基またはエトキシ基を表し、R6及びR7はメチル基またはメトキシ基を表し、Q1〜Q4はそれぞれ独立に水素原子、炭素原子数1〜2の低級アルキル基若しくは低級アルコシキシル基または水酸基を表し、Wは、化4に示される基から選択される置換基であり、mは0又は1の整数を表し、A及びBは、それぞれ独立に−NH−Y−SO3Hで示される基または水酸基の何れかであり、ここでYは、エチレン基、フェニレン基、及びナフチレン基から選択される基であって置換基を含むものであっても良い。〕
- 上記一般式(1)で表されるモノアゾ黄色主顔料98〜80モル%と、上記一般式(2)で示されるジスアゾ黄色顔料またはその塩、及び/または、上記一般式(3)で示されるモノアゾ黄色顔料またはその塩2〜20モル%をと含むことを特徴とする請求項1記載の水性顔料分散体。
- 中和されたアニオン性基含有有機高分子化合物のアニオン性基が、カルボキシル基及びカルボキシラート基である請求項1または2記載の水性顔料分散体。
- カルボキシラート基の対イオンが、アンモニウムイオンおよびアルカリ金属イオンからなる群から選ばれるカチオンである請求項3記載の水性顔料分散体。
- アニオン性基含有有機高分子化合物の重量平均分子量が、5,000〜50,000である請求項1、2、3または4のいずれか記載の水性顔料分散体。
- アニオン性基含有有機高分子化合物の酸価が、30〜220mgKOH/g及びガラス転移点が−20〜100℃である請求項1、2、3、4または5のいずれか記載の水性顔料分散体。
- 前記各顔料またはその塩の合計とアニオン性基含有有機高分子化合物の比率が、質量換算で、前記各顔料またはその塩の合計100部に対してアニオン性基含有有機高分子化合物が10〜200部である請求項1、2、3、4、5または6のいずれか記載の水性顔料分散体。
- 請求項1、2、3、4、5、6または7のいずれか記載の水性顔料分散体を含有することを特徴とする水性顔料記録液。
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