CA2505613A1 - Benzimidazole-pyridone-based azo dyes - Google Patents
Benzimidazole-pyridone-based azo dyes Download PDFInfo
- Publication number
- CA2505613A1 CA2505613A1 CA002505613A CA2505613A CA2505613A1 CA 2505613 A1 CA2505613 A1 CA 2505613A1 CA 002505613 A CA002505613 A CA 002505613A CA 2505613 A CA2505613 A CA 2505613A CA 2505613 A1 CA2505613 A1 CA 2505613A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- formula
- unsubstituted
- aryl
- azo dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000987 azo dye Substances 0.000 title claims abstract description 59
- 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
- -1 -SO3M Chemical group 0.000 claims abstract description 50
- 239000002023 wood Substances 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000007639 printing Methods 0.000 claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
- 229910052736 halogen Chemical group 0.000 claims abstract description 16
- 150000002367 halogens Chemical group 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
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 12
- 150000001768 cations Chemical class 0.000 claims abstract description 11
- 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
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000003254 radicals Chemical class 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
- 239000000463 material Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 239000004753 textile Substances 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- 238000004040 coloring Methods 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 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
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000913 palmityl 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])[H] 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 9
- 239000003960 organic solvent Substances 0.000 abstract description 9
- 239000000976 ink Substances 0.000 abstract description 3
- 239000008199 coating composition Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 23
- 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 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 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
- 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
- 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
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-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
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940032330 sulfuric acid Drugs 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- 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
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052799 carbon 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
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000758 substrate Substances 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
- 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 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- SYVYJDDQVKAXGE-UHFFFAOYSA-N amino(hydroxysulfamoyl)sulfamic acid Chemical group OS(=O)(=O)N(N)S(=O)(=O)NO SYVYJDDQVKAXGE-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
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- 239000002917 insecticide Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)(C=C1)C=Cc(nc2C(*)=C(*)C3=NN*)c1[n]2C3=O Chemical compound CC(*)(C=C1)C=Cc(nc2C(*)=C(*)C3=NN*)c1[n]2C3=O 0.000 description 1
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Classifications
-
- 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)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2058/02 | 2002-12-05 | ||
| CH20582002 | 2002-12-05 | ||
| PCT/EP2003/050898 WO2004050768A2 (en) | 2002-12-05 | 2003-11-26 | Benzimidazole-pyridone-based azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2505613A1 true CA2505613A1 (en) | 2004-06-17 |
Family
ID=32399980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002505613A Abandoned CA2505613A1 (en) | 2002-12-05 | 2003-11-26 | Benzimidazole-pyridone-based azo dyes |
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) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE518920T1 (de) * | 2004-12-29 | 2011-08-15 | Basf Se | In organischen lösungsmitteln lösliche farbstoffe |
| JP5144278B2 (ja) * | 2006-01-06 | 2013-02-13 | 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 |
| TW200833792A (en) * | 2006-11-08 | 2008-08-16 | Nippon Kayaku Kk | Azo compound, ink composition, recording method and colored article |
| 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 |
| 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 |
| JPWO2009078253A1 (ja) * | 2007-12-14 | 2011-04-28 | 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 |
| JP5268414B2 (ja) * | 2008-04-25 | 2013-08-21 | 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 |
| 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 |
| JP5382783B2 (ja) * | 2009-03-23 | 2014-01-08 | 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 |
| JPWO2010109843A1 (ja) * | 2009-03-27 | 2012-09-27 | 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 |
| 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 |
| 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 |
| 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 |
| US8932393B2 (en) | 2010-12-17 | 2015-01-13 | Nippon Kayaku Kabushiki Kaisha | Azo compound, ink composition, recording method and colored material |
| 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 |
| FR2990852A1 (fr) * | 2012-05-24 | 2013-11-29 | Oreal | Colorant ou azurant anionique a contre ion ammonium ou phosphonium, composition de teinture les comprenant et procede de coloration des fibres keratiniques a partir de ces colorants |
| 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
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 |
| JP2006509068A (ja) | 2006-03-16 |
| EP1570004A2 (en) | 2005-09-07 |
| WO2004050768A3 (en) | 2004-08-12 |
| KR20050085375A (ko) | 2005-08-29 |
| WO2004050768A2 (en) | 2004-06-17 |
| CN1720298A (zh) | 2006-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |