JP6712833B2 - キサンテン化合物、着色組成物 - Google Patents
キサンテン化合物、着色組成物 Download PDFInfo
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- JP6712833B2 JP6712833B2 JP2016192407A JP2016192407A JP6712833B2 JP 6712833 B2 JP6712833 B2 JP 6712833B2 JP 2016192407 A JP2016192407 A JP 2016192407A JP 2016192407 A JP2016192407 A JP 2016192407A JP 6712833 B2 JP6712833 B2 JP 6712833B2
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- carbon atoms
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- acrylate
- meth
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- -1 Xanthene compound Chemical class 0.000 title claims description 142
- 239000000203 mixture Substances 0.000 title claims description 91
- 238000004040 coloring Methods 0.000 title claims description 78
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 title claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000000049 pigment Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000003368 amide group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000004973 liquid crystal related substance Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 238000003384 imaging method Methods 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- 239000000975 dye Substances 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 27
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
- 238000009833 condensation Methods 0.000 description 26
- 230000005494 condensation Effects 0.000 description 26
- 229920001577 copolymer Polymers 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 16
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000976 ink Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical group CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
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- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 3
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 125000006606 n-butoxy group Chemical group 0.000 description 3
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 0.000 description 3
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- 238000003756 stirring Methods 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
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 3
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 2
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- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Description
[1]下記式(1)で表されるキサンテン化合物
[2]式(1)におけるR1及びR2が、無置換の炭素数1乃至4のアルキル基、ハロゲン原子、アルコキシ基、シアノ基及びアミド基からなる群より選ばれる置換基を有する炭素数6乃至10の一価の芳香族炭化水素基である前項[1]に記載のキサンテン化合物、
[3]式(1)におけるQが無置換の炭素数2乃至4のアルキレン基である前項[1]又は[2]に記載のキサンテン化合物、
[4]式(1)におけるR3及びR4が水素原子又は無置換の炭素数1乃至4のアルキル基である前項[1]乃至[3]のいずれか一項に記載のキサンテン化合物、
[5]前項[1]乃至[4]のいずれか一項に記載のキサンテン化合物を含む着色組成物、
[6]更に、顔料を含む前項[5]に記載の着色組成物、
[7]前項[5]又は[6]に記載の着色組成物を用いて得られるカラーフィルター、
[8]前項[7]に記載のカラーフィルターを装着した液晶表示装置、有機ELディスプレイ又は固体撮像素子、
に関する。
式(1)中、R1及びR2は、水素原子、炭素数1乃至10のアルキル基又は炭素数6乃至10の一価の芳香族炭化水素基を表し、該炭素数1乃至10のアルキル基及び炭素数6乃至10の一価の芳香族炭化水素基がそれらの構造中に有する水素原子は置換基で置換されていてもよい。
尚、本明細書では、構造中に有する水素原子が置換基で置換されていない「アルキル基」及び「芳香族炭化水素基」を、それぞれ「無置換のアルキル基」及び「無置換の芳香族炭化水素基」と記載する。
式(1)のQが表す無置換のアルキレン基とは、炭素原子と水素原子のみからなる直鎖状、分岐鎖状又は環状のアルキル基から水素原子1個を除いた2価の連結基を意味し、無置換の炭素数2乃至4のアルキレン基であることが好ましい。
合成スキームにおける式(2)乃至(9)中のR1乃至R6及びQは、前記式(1)におけるR1乃至R6及びQと同義である。式(7)及び(9)中のX及びZは一般的な脱離基(例えば、ハロゲン原子(ヨウ素原子、臭素原子及び塩素原子等)、トシラート基又はメシラート基等)である。
得られた式(6)で表される化合物のNH基に、脱離基Xを有する化合物(上記合成スキーム例において式(7)で表される化合物)を所定温度(例えば20乃至100℃)で縮合させ得た化合物(上記合成スキーム例において式(8)で表される化合物)に、更に対応する脱離基Zを有する化合物(上記合成スキーム例において式(9)で表される化合物)を所定温度(例えば30乃至150℃)で縮合させることにより本発明の式(1)で表される化合物を得ることができる。
その他の成分としては、例えば油溶性有機溶媒、水溶性有機溶媒並びに水等の溶媒類や樹脂類、更にはこれらの溶媒類や樹脂類と組み合わせて用い得る各種の添加剤等が挙げられ、これらの一種又は二種以上を着色組成物の用途や用法に合せて特に制限なく用いることが出来るが、最も単純な着色組成物としては、式(1)で表されるキサンテン化合物と溶媒類を含有する組成物が挙げられる。
油溶性有機溶媒と併用し得る分散剤としては、ドデシルベンゼンスルホン酸ナトリウム、ラウリル酸ナトリウム、ナフタレンスルホン酸のホルマリン縮合物、アルキルナフタレンスルホン酸のホルマリン縮合物、クレオソート油スルホン酸のホルマリン縮合物、ポリオキシエチレンアルキルエーテルサルフェートのアンモニウム塩、ポリオキシエチレンアルキルフェニルエーテルサルフェートのアンモニウム塩、ポリオキシアルキルエーテル燐酸エステル塩等公知のアニオン界面活性剤、ビニルナフタレン誘導体、α、β−エチレン性不飽和カルボン酸の脂肪族アルコールエステル等、スチレン、スチレン誘導体、アクリル酸、アクリル酸誘導体、メタクリル酸、メタクリル酸誘導体、マレイン酸、マレイン酸誘導体、無水マレイン酸、無水マレイン酸誘導体、イタコン酸、イタコン酸誘導体、フマール酸、フマール酸誘導体等から選ばれた少なくとも2つ以上の単量体からなるブロック共重合体、或いはランダム共重合体、又はこれらの塩等の高分子分散剤等が挙げられる。
本発明の着色組成物が含有し得るポリアミド樹脂、ポリウレタン樹脂、ポリエステル樹脂、エポキシ樹脂及びポリアクリル樹脂としては、特に限定されず従来公知のものが挙げられる。
消泡剤としては、シリコーン系、アセチレン系の公知の消泡剤が挙げられる。
防腐・防黴剤としてはデヒドロ酢酸ナトリウム、安息香酸ナトリウム、ソジウムピリジンチオン−1−オキサイド、ジンクピリジンチオン−1−オキサイド、1,2−ベンズイソチアゾリン−3−オン、1−ベンズイソチアゾリン−3−オンのアミン塩等の公知の防腐・防黴剤が挙げられる。
pH調整剤としては水酸化ナトリウム、水酸化カリウム、水酸化リチウム等の水酸化アルカリ金属類、トリエタノールアミン、ジエタノールアミン、ジメチルエタノールアミン、ジエチルエタノールアミン等の3級アミン類等の公知のpH調整剤が挙げられる。
本発明の着色組成物を用いる被着色材料としては、例えば普通紙、コート紙、プラスチックフィルム、プラスチック基板が挙げられるが、これらに限定されるものではない。また、本発明の着色組成物を被着色材料に付与する方法としては、オフセット印刷、凸版印刷、フレキソ印刷、インクジェット印刷などの各種印刷方法あるいはスピンコーター、ロールコーターなどによる塗工方法が挙げられる。
(工程1−1)
300mlの四つ口フラスコに、上記式(2)で表される化合物40.5部、NMP120部及び2,6−ジメチルアニリン(東京化成工業社製)48.4部を入れ、160℃で5時間攪拌した。反応液を30℃まで冷却した後、反応液を2N塩酸水に注ぎ込み1時間攪拌した。析出した結晶をろ取、洗浄、乾燥させることにより、下記式(100)で表される染料中間体53.1部を得た。
500mlの四つ口フラスコに、ジメチルホルムアミド343部、トリエチルアミン31.6部及び2−クロロエチルアミン塩酸塩(東京化成工業社製)33.2部を入れ、10分間攪拌した。これにp−トルエンスルホニルクロリド(東京化成工業社製)49.6部を、液温が20℃を超えないように少しずつ添加し、室温で3時間攪拌した。反応液を冷却した5%塩酸水に注ぎ込み、15分間攪拌、析出した結晶をろ取、洗浄、乾燥させることにより、下記式(101)で表される染料中間体33.8部を得た。
300mlの四つ口フラスコに、工程1−1で得られた式(100)で表される染料中間体9部、N−メチル−2−ピロリドン80部、炭酸カリウム4.3部、ヨウ化カリウム(純正化学工業社製)6.5部及び工程1−2で得られた式(101)で表される染料中間体9.1部を入れ、90℃で3時間攪拌した。反応液を40℃まで冷却した後、反応液を水に注ぎ込み、析出した結晶をろ取、洗浄、乾燥させることにより、No.1で表される本発明のキサンテン化合物13.4部を得た。該キサンテン化合物の最大吸収波長は544nm(メタノール)であった。
(工程2−1)
500mlの四つ口フラスコに、ジクロロメタン473部、トリエチルアミン82.7部及び2−(メチルアミノ)エタノール(東京化成工業社製)28.5部を入れ、10分間攪拌した。これにp−トルエンスルホニルクロリド148.5部を、液温が20℃を超えないように少しずつ添加し、室温で20時間攪拌した。反応液に水を注ぎ、有機層を希塩酸水、水、飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥した。更に減圧下で濃縮することにより、下記式(102)で表される染料中間体140部を得た。
200mlの四つ口フラスコに、N−メチル−2−ピロリドン75部、臭化カリウム(純正化学工業社製)17.9部及び工程2−1で得られた式(102)で表される染料中間体19.2部を入れ、80℃で2時間攪拌した。反応液に水を注ぎ、有機層を希塩酸水、水、飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥した。更に減圧下で濃縮することにより、下記式(103)で表される染料中間体10.2部を得た。
300mlの四つ口フラスコに、実施例1の工程1−1で得られた式(100)で表される染料中間体9.0部、N−メチル−2−ピロリドン80部、炭酸カリウム4.3部、ヨウ化カリウム6.5部及び工程2−2で得られた式(103)で表される染料中間体12.4部を入れ、100乃至110℃で3時間攪拌した。反応液を40℃まで冷却した後、反応液を水に注ぎ込み、析出した結晶をろ取、洗浄、乾燥させることにより、No.3で表される本発明のキサンテン化合物13.1部を得た。該キサンテン化合物の最大吸収波長は544nm(メタノール)であった。
(工程3−1)
1000mlの四つ口フラスコに、ジクロロメタン282部、トリエチルアミン32.6部及び2−(ブチルアミノ)エタノール(東京化成工業社製)17.6部を入れ、10分間攪拌した。これにp−トルエンスルホニルクロリド58.6部を、液温が20℃を超えないように少しずつ添加し、室温で19時間攪拌した。反応液に水を注ぎ、有機層を希塩酸水、水、飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥した。更に減圧下で濃縮することにより、下記式(104)で表される染料中間体65.3部を得た。
200mlの四つ口フラスコに、N−メチル−2−ピロリドン75部、臭化カリウム17.9部及び工程3−1で得られた式(104)で表される染料中間体20部を入れ、80℃で2時間攪拌した。反応液に水を注ぎ、有機層を希塩酸水、水、飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥した。更に減圧下で濃縮することにより、下記式(105)で表される染料中間体11.4部を得た。
300mlの四つ口フラスコに、実施例1の工程1−1で得られた式(100)で表される染料中間体9.0部、N−メチル−2−ピロリドン80部、炭酸カリウム4.3部、ヨウ化カリウム6.5部及び工程3−2で得られた式(105)で表される染料中間体13部を入れ、100乃至110℃で4時間攪拌した。反応液を40℃まで冷却した後、反応液を水に注ぎ込み、析出した結晶をろ取、洗浄、乾燥させることにより、No.9で表される本発明のキサンテン化合物15.9部を得た。該キサンテン化合物の最大吸収波長は545nm(メタノール)であった。
(工程4−1)
300mlの四つ口フラスコに、上記式(2)で表される化合物40.5部、N−メチル−2−ピロリドン120部及び下記式(106)で表される化合物88.1部を入れ、160℃で6時間攪拌した。反応液を30℃まで冷却した後、反応液を2N塩酸水に注ぎ込み1時間攪拌した。析出した結晶をろ取、洗浄、乾燥させることにより、下記式(107)で表される染料中間体71.9部を得た。
300mlの四つ口フラスコに、工程4−1で得られた式(107)で表される染料中間体7.0部、N−メチル−2−ピロリドン45部、炭酸カリウム3.7部、ヨウ化カリウム3部及び実施例1の工程1−2で得られた式(101)で表される染料中間体7.5部を入れ、80℃で1時間半攪拌した。反応液を40℃まで冷却した後、反応液を水に注ぎ込み、析出した結晶をろ取、洗浄、乾燥させることにより、No.14で表される本発明のキサンテン化合物24.7部を得た。該キサンテン化合物の最大吸収波長は545nm(メタノール)であった。
(工程5−1)
100mlの四つ口フラスコに、実施例4の工程4−1で得られた式(107)で表される染料中間体3.5部、N−メチル−2−ピロリドン32部、炭酸カリウム1.9部、ヨウ化カリウム2.2部及び実施例2の工程2−2で得られた式(103)で表される染料中間体3.9部を入れ、90乃至100℃で14時間半攪拌した。反応液を40℃まで冷却した後、反応液を水に注ぎ込み、析出した結晶をろ取、洗浄、乾燥させることにより、No.15で表される本発明のキサンテン化合物7部を得た。該キサンテン化合物の最大吸収波長は545nm(メタノール)であった。
500mlの四つ口フラスコにメチルエチルケトン160部、メタクリル酸10部、ベンジルメタクリレート33部及びα,α’−アゾビス(イソブチロニトリル)1部を仕込み、攪拌しながら30分間窒素ガスをフラスコ内に流入した。その後、80℃まで昇温し、80乃至85℃でそのまま4時間攪拌した。反応終了後、室温まで冷却し、無色透明で均一な共重合体溶液を得た。これをイソプロピルアルコールと水の1:1混合溶液中で沈殿させ、濾過し、固形分を取り出し、乾燥し、バインダー樹脂を得た。得られたバインダー樹脂のポリスチレン換算重量平均分子量は18000であり、酸価は152(mgKOH/g)であった。
実施例1で得られたNo.1で表されるキサンテン化合物/Disperbyk−2001(ビックケミー・ジャパン製)/PGMEA(プロピレングリコールモノメチルエーテルアセテート)/エトキシプロパノール/合成例1で得られたバインダー樹脂=0.15部/0.5部/8.0部/1.0部/0.5部の組成比で混合した後、0.3mmジルコニアビーズ25部を添加し、ペイントシェーカーで3時間処理を行った。ビーズをろ過して除き、得られた着色組成物1をガラス基板にスピンコートし、80℃で10分間乾燥し、染料着色体1を作成した。
実施例1で得られたNo.1で表されるキサンテン化合物を、実施例2で得られたNo.3で表されるキサンテン化合物に変更したこと以外は実施例6と同様にして、着色組成物2及び染料着色体2を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、実施例3で得られたNo.9で表されるキサンテン化合物に変更したこと以外は実施例6と同様にして、着色組成物3及び染料着色体3を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、実施例4で得られたNo.14で表されるキサンテン化合物に変更したこと以外は実施例6と同様にして、着色組成物4及び染料着色体4を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、実施例5で得られたNo.15で表されるキサンテン化合物に変更したこと以外は実施例6と同様にして、着色組成物5及び染料着色体5を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、特許文献8に記載の下記式(A1)で表される化合物(下記8つの構造式で表される化合物の混合物)に変更したこと以外は実施例6と同様にして、比較用の着色組成物1及び比較用の染料着色体1を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、特許文献6に記載の下記式(A2)で表される化合物に変更したこと以外は実施例6と同様にして、比較用の着色組成物2及び比較用の染料着色体2を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、下記式(A3)で表されるC.I.Acid Red 52に変更したこと以外は実施例6と同様にして、比較用の着色組成物3及び比較用の染料着色体3を得た。
実施例1で得られたNo.1で表されるキサンテン化合物を、下記式(A4)で表される化合物(下記2つの構造式で表される化合物の混合物)に変更したこと以外は実施例6と同様にして、比較用の着色組成物4及び比較用の染料着色体4を得た。
実施例6乃至10及び比較例1乃至4で得られた染料着色体1乃至5及び比較用の染料着色体1乃至4に、230℃の恒温熱風乾燥機中で30分間の加熱処理を施した。処理前後の染料着色体のL値、a値、b値を、分光光度計を用いて標準光としてC光源、2度視野角で測色し、色差を求めた。尚、色差が小さいほど、色相の変化が少なく、耐熱堅牢度に優れていることを示す。結果を表1に示した。
実施例6乃至10及び比較例1乃至4で得られた染料着色体1乃至5及び比較用の染料着色体1乃至4を、分光光度計により分光透過率を測定し、C光源のCIEのXYZ表色系におけるx、yの色度座標と明度Yを評価した。尚、明度Yが大きい程、明度が高く、優れていることを示す。結果を表1に示した。
Claims (9)
- 下記式(1)で表されるキサンテン化合物
- 式(1)におけるR1及びR2が、無置換の炭素数1乃至4のアルキル基、ハロゲン原子、アルコキシ基、シアノ基及びアミド基からなる群より選ばれる置換基を有する炭素数6乃至10の一価の芳香族炭化水素基である請求項1に記載のキサンテン化合物。
- 式(1)におけるQが無置換の炭素数2乃至4のアルキレン基である請求項1又は2に記載のキサンテン化合物。
- 式(1)におけるR3及びR4が水素原子又は無置換の炭素数1乃至4のアルキル基である請求項1乃至3のいずれか一項に記載のキサンテン化合物。
- 式(1)におけるR 5 及びR 6 が炭素数1乃至3のアルキル基を置換基として有するフェニル基である請求項1乃至4のいずれか一項に記載のキサンテン化合物。
- 請求項1乃至5のいずれか一項に記載のキサンテン化合物を含む着色組成物。
- 更に、顔料を含む請求項6に記載の着色組成物。
- 請求項6又は7に記載の着色組成物を用いて得られるカラーフィルター。
- 請求項8に記載のカラーフィルターを装着した液晶表示装置、有機ELディスプレイ又は固体撮像素子。
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