JP2006509068A - ベンゾイミダゾール−ピリドンをベースとするアゾ染料 - Google Patents
ベンゾイミダゾール−ピリドンをベースとするアゾ染料 Download PDFInfo
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- JP2006509068A JP2006509068A JP2004556335A JP2004556335A JP2006509068A JP 2006509068 A JP2006509068 A JP 2006509068A JP 2004556335 A JP2004556335 A JP 2004556335A JP 2004556335 A JP2004556335 A JP 2004556335A JP 2006509068 A JP2006509068 A JP 2006509068A
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- Prior art keywords
- substituted
- formula
- unsubstituted
- aryl
- wood
- Prior art date
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- 239000000987 azo dye Substances 0.000 title claims description 57
- BATPFGQVSYIKDD-UHFFFAOYSA-N 1h-benzimidazole;1h-pyridin-2-one Chemical compound O=C1C=CC=CN1.C1=CC=C2NC=NC2=C1 BATPFGQVSYIKDD-UHFFFAOYSA-N 0.000 title description 2
- 239000002023 wood Substances 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 239000003086 colorant Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000007639 printing Methods 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 150000001768 cations Chemical class 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 229920003023 plastic Polymers 0.000 claims abstract description 8
- 239000004033 plastic Substances 0.000 claims abstract description 8
- 239000002245 particle Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 26
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 239000004744 fabric Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 238000004040 coloring Methods 0.000 claims description 8
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 239000002657 fibrous material Substances 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 10
- 239000008199 coating composition Substances 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- -1 tert-amyl (1, 1-dimethylpropyl) Chemical group 0.000 description 29
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- 239000004952 Polyamide Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- SYVYJDDQVKAXGE-UHFFFAOYSA-N amino(hydroxysulfamoyl)sulfamic acid Chemical group OS(=O)(=O)N(N)S(=O)(=O)NO SYVYJDDQVKAXGE-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- ZCDOAXPGUPHABM-UHFFFAOYSA-N 2-(2-oxoimidazo[4,5-f]quinolin-4-yl)acetonitrile Chemical compound C1=CC=C2C3=NC(=O)N=C3C(CC#N)=CC2=N1 ZCDOAXPGUPHABM-UHFFFAOYSA-N 0.000 description 2
- DCYBHNIOTZBCFS-UHFFFAOYSA-N 2-amino-5-[(4-sulfophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 DCYBHNIOTZBCFS-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- BYGSJVVYZDZMFU-UHFFFAOYSA-N C(C)(=O)NN(S(=O)(=O)N)S(=O)(=O)O Chemical compound C(C)(=O)NN(S(=O)(=O)N)S(=O)(=O)O BYGSJVVYZDZMFU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- OPOJRMTZHYUKLY-UHFFFAOYSA-N 1h-1,3,5-triazin-2-one Chemical compound O=C1N=CN=CN1 OPOJRMTZHYUKLY-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH20582002 | 2002-12-05 | ||
| PCT/EP2003/050898 WO2004050768A2 (en) | 2002-12-05 | 2003-11-26 | Benzimidazole-pyridone-based azo dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006509068A true JP2006509068A (ja) | 2006-03-16 |
| JP2006509068A5 JP2006509068A5 (enExample) | 2007-01-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004556335A Withdrawn JP2006509068A (ja) | 2002-12-05 | 2003-11-26 | ベンゾイミダゾール−ピリドンをベースとするアゾ染料 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7217803B2 (enExample) |
| EP (1) | EP1570004A2 (enExample) |
| JP (1) | JP2006509068A (enExample) |
| KR (1) | KR20050085375A (enExample) |
| CN (1) | CN1720298A (enExample) |
| AU (1) | AU2003298325A1 (enExample) |
| BR (1) | BR0316989A (enExample) |
| CA (1) | CA2505613A1 (enExample) |
| MX (1) | MXPA05005928A (enExample) |
| WO (1) | WO2004050768A2 (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007077931A1 (ja) | 2006-01-06 | 2007-07-12 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| WO2008056626A1 (en) * | 2006-11-08 | 2008-05-15 | Nippon Kayaku Kabushiki Kaisha | Azo compound, ink composition, recording method, and colored body |
| WO2009069279A1 (ja) * | 2007-11-27 | 2009-06-04 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、プリント方法及び着色体 |
| WO2009078253A1 (ja) * | 2007-12-14 | 2009-06-25 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| JP2009263513A (ja) * | 2008-04-25 | 2009-11-12 | Nippon Kayaku Co Ltd | アゾ化合物、インク組成物、記録方法及び着色体 |
| WO2010109843A1 (ja) * | 2009-03-27 | 2010-09-30 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
| JP2010222442A (ja) * | 2009-03-23 | 2010-10-07 | Nippon Kayaku Co Ltd | アゾ化合物、インク組成物、記録方法及び着色体 |
| WO2012008360A1 (ja) * | 2010-07-13 | 2012-01-19 | Jsr株式会社 | 着色剤、着色組成物、カラーフィルタ及び表示素子 |
| WO2012081640A1 (ja) * | 2010-12-17 | 2012-06-21 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
| JP2015517558A (ja) * | 2012-05-24 | 2015-06-22 | ロレアル | アンモニウム又はホスホニウム対イオンを担持するアニオン性染料又は光沢剤、これらを含む染料組成物、及びこれらの染料を使用してケラチン繊維を染色する方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE518920T1 (de) * | 2004-12-29 | 2011-08-15 | Basf Se | In organischen lösungsmitteln lösliche farbstoffe |
| JPWO2008096697A1 (ja) * | 2007-02-05 | 2010-05-20 | 日本化薬株式会社 | トリスアゾ化合物、インク組成物、プリント方法及び着色体 |
| JP5456666B2 (ja) | 2008-05-07 | 2014-04-02 | 日本化薬株式会社 | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| GB0905732D0 (en) * | 2009-04-03 | 2009-05-20 | Fujifilm Imaging Colorants Ltd | Polyazo dyes and their use in ink-jet printing |
| WO2010143610A1 (ja) | 2009-06-12 | 2010-12-16 | 日本化薬株式会社 | トリスアゾ化合物からなる色素、インク組成物、記録方法及び着色体 |
| FR2967684B1 (fr) | 2010-11-18 | 2015-09-11 | Oreal | Colorant direct anionique a contre ion tetra-alkylammonium, composition de teinture les comprenant et procede de coloration des fibres keratiniques a partir de ces colorants |
| US8864891B2 (en) | 2010-12-17 | 2014-10-21 | Nippon Kayaku Kabushiki Kaisha | Ink composition, inkjet recording method and colored body |
| DE102011082916A1 (de) | 2011-09-19 | 2012-06-14 | Henkel Ag & Co. Kgaa | Kationische, tricyclische Azofarbstoffe zum Färben von keratinhaltigen Fasern |
| CN102964374B (zh) * | 2012-11-28 | 2015-10-28 | 玉林师范学院 | 一种苯并咪唑吡啶类配合物及其制备方法 |
| US10323150B2 (en) | 2015-09-25 | 2019-06-18 | Nippon Kayaku Kabushiki Kaisha | Azo compound, ink composition, ink jet recording method, and colored article |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2004488A1 (en) | 1970-01-31 | 1971-08-05 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Water-soluble azo dyes for wool and poly-amide fibres |
| DE2023295A1 (en) | 1970-05-13 | 1971-11-25 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Water insoluble azo dyes for dyeing polyesters polyamides cellulose - esters and polypropylene |
| NL173862C (nl) * | 1971-08-10 | 1984-03-16 | Ciba Geigy | Werkwijze ter bereiding van ammoniumzouten van anionogene kleurstoffen. |
| CH591540A5 (enExample) * | 1974-03-12 | 1977-09-30 | Ciba Geigy Ag | |
| DE2701659A1 (de) | 1977-01-17 | 1978-07-20 | Basf Ag | Verbindungen der pyridinreihe |
-
2003
- 2003-11-26 CA CA002505613A patent/CA2505613A1/en not_active Abandoned
- 2003-11-26 CN CNA2003801050718A patent/CN1720298A/zh active Pending
- 2003-11-26 JP JP2004556335A patent/JP2006509068A/ja not_active Withdrawn
- 2003-11-26 AU AU2003298325A patent/AU2003298325A1/en not_active Abandoned
- 2003-11-26 BR BR0316989-8A patent/BR0316989A/pt not_active Application Discontinuation
- 2003-11-26 US US10/537,063 patent/US7217803B2/en not_active Expired - Fee Related
- 2003-11-26 KR KR1020057010183A patent/KR20050085375A/ko not_active Ceased
- 2003-11-26 EP EP03796059A patent/EP1570004A2/en not_active Withdrawn
- 2003-11-26 MX MXPA05005928A patent/MXPA05005928A/es not_active Application Discontinuation
- 2003-11-26 WO PCT/EP2003/050898 patent/WO2004050768A2/en not_active Ceased
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| WO2007077931A1 (ja) | 2006-01-06 | 2007-07-12 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| WO2008056626A1 (en) * | 2006-11-08 | 2008-05-15 | Nippon Kayaku Kabushiki Kaisha | Azo compound, ink composition, recording method, and colored body |
| JP5334864B2 (ja) * | 2007-11-27 | 2013-11-06 | 日本化薬株式会社 | トリスアゾ化合物、インク組成物、プリント方法及び着色体 |
| WO2009069279A1 (ja) * | 2007-11-27 | 2009-06-04 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、プリント方法及び着色体 |
| US7901498B2 (en) | 2007-11-27 | 2011-03-08 | Nippon Kayaku Kabushiki Kaisha | Trisazo compound, ink composition, printing method and colored product |
| WO2009078253A1 (ja) * | 2007-12-14 | 2009-06-25 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| JP2009263513A (ja) * | 2008-04-25 | 2009-11-12 | Nippon Kayaku Co Ltd | アゾ化合物、インク組成物、記録方法及び着色体 |
| JP2010222442A (ja) * | 2009-03-23 | 2010-10-07 | Nippon Kayaku Co Ltd | アゾ化合物、インク組成物、記録方法及び着色体 |
| WO2010109843A1 (ja) * | 2009-03-27 | 2010-09-30 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
| WO2012008360A1 (ja) * | 2010-07-13 | 2012-01-19 | Jsr株式会社 | 着色剤、着色組成物、カラーフィルタ及び表示素子 |
| JPWO2012008360A1 (ja) * | 2010-07-13 | 2013-09-09 | Jsr株式会社 | 着色剤、着色組成物、カラーフィルタ及び表示素子 |
| WO2012081640A1 (ja) * | 2010-12-17 | 2012-06-21 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
| JPWO2012081640A1 (ja) * | 2010-12-17 | 2014-05-22 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
| US8932393B2 (en) | 2010-12-17 | 2015-01-13 | Nippon Kayaku Kabushiki Kaisha | Azo compound, ink composition, recording method and colored material |
| RU2583253C2 (ru) * | 2010-12-17 | 2016-05-10 | Ниппон Каяку Кабушики Кайша | Азосоединение, композиция чернил, способ записи и окрашенный материал |
| JP2015517558A (ja) * | 2012-05-24 | 2015-06-22 | ロレアル | アンモニウム又はホスホニウム対イオンを担持するアニオン性染料又は光沢剤、これらを含む染料組成物、及びこれらの染料を使用してケラチン繊維を染色する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003298325A8 (en) | 2004-06-23 |
| AU2003298325A1 (en) | 2004-06-23 |
| BR0316989A (pt) | 2005-10-25 |
| US7217803B2 (en) | 2007-05-15 |
| US20060053571A1 (en) | 2006-03-16 |
| MXPA05005928A (es) | 2005-12-05 |
| EP1570004A2 (en) | 2005-09-07 |
| WO2004050768A3 (en) | 2004-08-12 |
| KR20050085375A (ko) | 2005-08-29 |
| CA2505613A1 (en) | 2004-06-17 |
| WO2004050768A2 (en) | 2004-06-17 |
| CN1720298A (zh) | 2006-01-11 |
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