CN111902489B - Complex salt compound, dye composition, coloring agent for anodized aluminum, coloring method, and method for producing complex salt compound - Google Patents
Complex salt compound, dye composition, coloring agent for anodized aluminum, coloring method, and method for producing complex salt compound Download PDFInfo
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- CN111902489B CN111902489B CN201980021998.4A CN201980021998A CN111902489B CN 111902489 B CN111902489 B CN 111902489B CN 201980021998 A CN201980021998 A CN 201980021998A CN 111902489 B CN111902489 B CN 111902489B
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- 238000004040 coloring Methods 0.000 title claims abstract description 31
- 229910052782 aluminium Inorganic materials 0.000 title claims description 91
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims description 84
- 239000000203 mixture Substances 0.000 title claims description 42
- 239000003086 colorant Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- -1 salt compound Chemical class 0.000 title description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 164
- 125000001424 substituent group Chemical group 0.000 claims abstract description 128
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 29
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 11
- 150000001768 cations Chemical class 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052804 chromium Inorganic materials 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 238000006149 azo coupling reaction Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910000838 Al alloy Inorganic materials 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 description 80
- 239000000975 dye Substances 0.000 description 56
- 235000002639 sodium chloride Nutrition 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000004043 dyeing Methods 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 17
- 239000007788 liquid Substances 0.000 description 15
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 239000011651 chromium Substances 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000011148 porous material Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000987 azo dye Substances 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 5
- 244000144730 Amygdalus persica Species 0.000 description 5
- 229910000906 Bronze Inorganic materials 0.000 description 5
- 235000006040 Prunus persica var persica Nutrition 0.000 description 5
- 244000269722 Thea sinensis Species 0.000 description 5
- 238000007743 anodising Methods 0.000 description 5
- 239000010974 bronze Substances 0.000 description 5
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 5
- 238000005238 degreasing Methods 0.000 description 5
- 238000005868 electrolysis reaction Methods 0.000 description 5
- 238000005562 fading Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 3
- GAPXKZLRPJFAKS-UHFFFAOYSA-N 5-oxo-1-(4-sulfophenyl)-4h-pyrazole-3-carboxylic acid;sodium Chemical compound [Na].O=C1CC(C(=O)O)=NN1C1=CC=C(S(O)(=O)=O)C=C1 GAPXKZLRPJFAKS-UHFFFAOYSA-N 0.000 description 3
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000002048 anodisation reaction Methods 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- 125000006039 1-hexenyl group Chemical group 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000010407 anodic oxide Substances 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000004623 carbolinyl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 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 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 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 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 239000001048 orange dye Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- YSNMMQRIPFUHAO-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carbonitrile Chemical compound CCN1C(O)=C(C#N)C(C)=CC1=O YSNMMQRIPFUHAO-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- NDELSWXIAJLWOU-UHFFFAOYSA-N 2,5-dimethyl-4h-pyrazol-3-one Chemical compound CN1N=C(C)CC1=O NDELSWXIAJLWOU-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- SGGKDRQNHWHJNA-UHFFFAOYSA-N [Na].CC1=NN(C(C1)=O)C1=CC=C(C=C1)S(=O)(=O)O Chemical compound [Na].CC1=NN(C(C1)=O)C1=CC=C(C=C1)S(=O)(=O)O SGGKDRQNHWHJNA-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- 238000005237 degreasing agent Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 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 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Optical Filters (AREA)
Abstract
The present invention relates to a compound represented by the following general formula (1). [ in the formula (1), R 1 ～R 4 Each independently represents-H, -SO 3 ‑ 、‑NO 2 Etc. R 1 ～R 4 Adjacent groups may be bonded to each other to form a ring, M represents Cr or the like, X represents a non-coloring cation, k represents an integer of 1 to 8, Y represents-O-, or the like, and Z represents groups represented by the following general formulae (2 a) to (2 k).][ in the formula, R 5 ～R 47 Each independently represents-H, -CN, -COOH, a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, R 48 ～R 51 Each independently represents-H or-SO 3 ‑ A represents an oxygen atom or the like, 1 represents a bonding end to a nitrogen atom, and 2 represents a bonding end to an oxygen atom.]
Description
Technical Field
The present invention relates to a complex salt compound, a dye composition containing the complex salt compound, a coloring agent for anodized aluminum containing the dye composition, a method for coloring anodized aluminum using the dye composition, and a method for producing the complex salt compound.
Background
Conventionally, as a method for coloring an aluminum (including aluminum oxide, aluminum alloy, and the like) surface, there has been used a method in which an electric current is applied to an aluminum as an anode in an electrolytic solution containing water and an appropriate acid to thereby perform a treatment (hereinafter, referred to as "anodization" or "alumite") of forming a porous alumina layer (oxide film, generally referred to as "alumite") on the aluminum surface, and thereafter: electrolytic coloring method using an inorganic compound or a metal compound; a dyeing method using an inorganic dye or an organic dye (an azo dye, a complex salt compound dye of a dye molecule and a metal atom, or the like, an acid dye, a direct dye, or the like) as a colorant (see patent documents 1 to 14).
There is a problem that the dye used for the colorant is poor in light fastness, and in order to improve the light fastness of colored aluminum, dyes of various complex salt compounds have been developed, and these colors are mostly black or gray (for example, patent documents 1 to 6), and in order to meet the recent demand for various colored aluminum, dyeing methods of dyes that can cope with various colors have been developed (for example, patent documents 7 to 10). In addition, development of additives for improving light resistance when organic dyes are used has also been carried out (for example, see patent document 8).
On the other hand, the following methods have also been developed: the anodized aluminum is colored to cyan, green, yellow, red, and other colors by changing the voltage condition of anodization using an electrolytic solution containing an organic acid or an inorganic acid without using a general dye (patent documents 11 to 13, etc.), but the type of color is limited.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 55-60562
Patent document 2: japanese laid-open patent publication No. 55-97492
Patent document 3: japanese laid-open patent publication No. 9-302256
Patent document 4: japanese laid-open patent publication No. Sho 60-235867
Patent document 5: japanese laid-open patent publication No. 6-93195
Patent document 6: japanese Kohyo publication No. 2002-522617
Patent document 7: japanese patent application laid-open No. 2013-506053
Patent document 8: japanese laid-open patent publication No. 2009-91622
Patent document 9: japanese patent application laid-open No. 2003-504426
Patent document 10: japanese patent laid-open No. 2000-290524
Patent document 11: japanese patent laid-open publication No. Sho 59-6397
Patent document 12: japanese laid-open patent publication No. 10-158890
Patent document 13: japanese laid-open patent publication No. 2000-96293
Patent document 14: japanese patent laid-open publication No. 2016-216803
Disclosure of Invention
Problems to be solved by the invention
In the colored aluminum market, for example, orange dyes are used to give gold hues in light colors, but aluminum etch-resistant dyes generally tend to fade more easily in light colors than in dark colors, and conventional orange dyes do not sufficiently secure light fastness when dyed in light colors. Further, in view of color stability (no color blur or fading), a colorant for developing a desired color using a monochromatic dye is required. Due to the above practical circumstances, the following dyes for anodized aluminum are desired: the dye is a monochromatic dye for developing orange-based colors and has high light resistance.
An object of one aspect of the present invention is to provide a complex salt compound having a novel structure capable of forming an anodized coating film which is excellent in light resistance and exhibits an orange color in a single color on the surface of aluminum, an aluminum oxide, or an aluminum alloy. Another object of the present invention is to provide a dye composition containing the complex salt compound, a coloring agent for anodized aluminum using the dye composition, a coloring method, and a method for producing the complex salt compound.
Means for solving the problems
In order to solve the above problems, the present inventors have conducted intensive studies on a coloring matter (dye) for anodizing aluminum, and as a result, they have found that: by using a complex salt compound (azo dye) having a specific structure as a coloring agent for anodized aluminum, it is possible to color an orange system color such as yellow, orange, red, peach, tea, bronze, etc. on anodized aluminum with a single-color dye, and to form a coating film having excellent light resistance. That is, the present invention relates to the following inventions.
[1] A compound represented by the following general formula (1).
[ solution 1]
[ in the formula (1),
R 1 ～R 4 each independently represents-H, -SO 3 - 、-NO 2 、-NO、-CN、-OH、-COO - 、-COOH、-SH、
An optionally substituted amino group having 0 to 20 carbon atoms,
A C0-20 sulfonyl group which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkyl group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkoxy group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
An optionally substituted acyl group having 1 to 20 carbon atoms,
An optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or
A heterocyclic group having 5 to 30 atoms in the ring which may have a substituent(s),
R 1 ～R 4 adjacent groups can be bonded to each other to form a ring，
M represents Cr, fe, co, si or Al atom,
x represents a non-color-developing cation, k represents an integer of 1 to 8,
y represents-O-or-O- (C = O) -,
z represents a group represented by the following general formulae (2 a) to (2 k). ]
[ solution 2]
[ in the formula,
R 5 ～R 47 each independently represents-H, -SO 3 - 、-NO 2 、-NO、-CN、-OH、-COO - 、-COOH、-SH、
An optionally substituted amino group having 0 to 20 carbon atoms,
A C0-20 sulfonyl group which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkyl group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkoxy group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
An optionally substituted acyl group having 1 to 20 carbon atoms,
An optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or
A heterocyclic group having 5 to 30 atoms which may have a substituent(s),
R 48 ～R 51 each independently represents-H or-SO 3 - ，
R 10 And R 11 、R 12 ～R 16 、R 17 ～R 21 、R 22 ～R 26 、R 27 And R 28 、R 29 ～R 34 、R 35 ～R 39 、R 40 ～R 45 And R 46 And R 47 Adjacent groups may be bonded to each other to form a ring,
a represents an oxygen atom or a sulfur atom,
and, n 1 represents a bonding end to a nitrogen atom, and n 2 represents a bonding end to an oxygen atom. ]
[2][1]The compound of the formula (1), wherein R is 1 ～R 4 Each independently represents-H, -SO 3 - 、-NO 2 、
An amino group having 0 to 10 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 10 carbon atoms which may have a substituent, or
An acyl group having 1 to 10 carbon atoms which may have a substituent.
[3] [1] or [2], wherein, in the general formulae (2 a) to (2 k),
R 5 is a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, R 6 is-COO - COOH, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an acyl group having 1 to 10 carbon atoms which may have a substituent,
R 7 or R 8 Each independently represents-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
R 9 ～R 11 each independently represents-H, -CN, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
R 12 ～R 16 each independently represents-H, may have a substituentA linear or branched alkyl group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
R 17 ～R 21 each independently-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
R 22 ～R 26 each independently represents-H, an amino group having 0 to 20 carbon atoms which may have a substituent, or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent,
R 27 and R 28 Each independently represents-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or a linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
R 29 ～R 34 each independently represents-H or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent,
R 35 ～R 39 each independently represents-H or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent,
R 40 ～R 42 and R 48 ～R 49 Any 1 or 2 of them is-SO 3 - or-COO - ，R 47 Is an amino group having 0 to 10 carbon atoms which may have a substituent, R 50 ～R 55 is-SO or 1 or 2 thereof 3 - or-COO - 。
[4] The compound according to any one of [1] to [3], wherein Z is a group represented by the formula (2 a), (2 b) or (2 c).
[5] A dye composition comprising the compound according to any one of [1] to [4 ].
[6] A coloring agent for anodized aluminum, which comprises the dye composition according to [5 ].
[7] A method for coloring an anodized aluminum, an anodized aluminum oxide or an anodized aluminum alloy, characterized by using a dye composition containing 0.02 to 10 mass% of the compound according to any one of [1] to [4 ].
[8] A method for producing a compound according to any one of [1] to [4], comprising the steps of: reacting a compound represented by the following general formula (I):
[ solution 3]
[ in the formula (I), R 1 ～R 4 Y and Z represent the same meanings as defined above.]
The compound represented by (1) is obtained by reacting a compound containing Cr, fe, co, si or Al atom with a compound represented by the general formula (1).
[8] [7] A production method wherein a compound represented by the general formula (I) is produced by reacting a compound represented by the following formula (II):
[ solution 4]
[ in the formula (II), R 1 ～R 4 And Y represents the same meaning as defined above.]
A diazo coupling reaction of a diazotized product obtained by diazotizing a compound represented by the formula (I) and/or a salt thereof with a coupler component,
the coupler component is represented by the following general formulas (III-a) to (III-k):
[ solution 5]
[ in the formula, R 5 ～R 55 And A represents the same meaning as defined above.]
A compound represented by any one of (1) and/or a salt thereof.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a complex salt compound having a novel structure capable of forming an anodized coating film which is excellent in light resistance and exhibits an orange color in a single color on the surface of aluminum, an aluminum oxide or an aluminum alloy can be provided. The dye composition containing the compound of the present invention can provide: a coloring agent for anodized aluminum, which is excellent in light resistance and can form a colored coating film exhibiting a single color of orange color such as yellow, orange, red, peach, tea, bronze, etc. Further, by using the coloring agent, an anodized aluminum coating film colored in an orange color such as yellow, orange, red, peach, tea, bronze, etc., and having excellent light resistance can be obtained. An anodized aluminum coating having excellent heat resistance in addition to light resistance can be formed by the dye composition containing the compound according to the present invention.
Detailed Description
The embodiments of the present invention will be described in detail below. The present invention is not limited to the following embodiments, and various modifications can be made within the scope of the present invention. The portion in the square bracket [ ] in the compound represented by the general formula (1) is an anion, and in the general formula (1), a complex is formed with a non-chromogenic cation represented by X.
The compound according to the present embodiment is a compound represented by the following general formula (1) (hereinafter also referred to as "compound (1)").
[ solution 6]
R 1 ～R 4 Each independently represents-H, -SO 3 - 、-NO 2 、-NO、-CN、-OH、-COO - COOH, -SH, an amino group having 0 to 20 carbon atoms which may have a substituent, a sulfonyl group having 0 to 20 carbon atoms which may have a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 20 carbon atoms which may have a substituent, a linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent, a cycloalkoxy group having 3 to 20 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent, and a cycloalkyl group having a substituentAn acyl group having 1 to 20 carbon atoms as a substituent, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a heterocyclic group having 5 to 30 carbon atoms as a ring which may have a substituent, R 1 ～R 4 Adjacent groups may be bonded to each other to form a ring, M represents a Cr, fe, co, si, or Al atom, X represents a non-coloring cation, k represents an integer of 1 to 8, Y represents-O-or-O- (C = O) -, and Z represents a group represented by the following general formulae (2 a) to (2 k).
Hereinafter, the compound (1) will be specifically described, but the present invention is not limited to these. The anion portion may have 1 structure in the range of the general formula (1) or may have a plurality of different structures from each other, but 1 structure is preferred. That is, there are a plurality of R 1 ～R 55 And Y may be the same as or different from each other. The number of the non-coloring cationic portions may be 1, or a plurality of them may be mixed, and 1 is preferred. When k is 2 to 8, a plurality of xs may be the same kind or different kinds.
In the general formula (1), as represented by R 1 ～R 4 The "amino group having 0 to 20 carbon atoms which may have a substituent" as shown above may include, for example, unsubstituted amino group (-NH) 2 ) Mono-substituted amino, di-substituted amino, and the like. The number of carbon atoms in the mono-or di-substituted amino group is, for example, 1 to 20, may be 1 to 10, and may be 2 to 6. The amino group having 0 to 20 carbon atoms which may have a substituent(s) may be a group in which an aromatic hydrocarbon group having 6 to 30 carbon atoms or a heterocyclic group having 5 to 30 ring atoms, which will be described later, is bonded via-NH-. Examples of the mono-substituted amino group include an ethylamino group, an acetylamino group, and a phenylamino group. Examples of the di-substituted amino group include a diethylamino group, a phenylamino group, a diphenylamino group, and an acetylphenylamino group. The mono-substituted amino group may be a group represented by-NHCO-R. The substituent R may be, for example, an alkyl group or an aryl group.
In the general formula (1), R is 1 ～R 4 The "optionally substituted sulfonyl group having 0 to 20 carbon atoms" means a sulfonyl group represented by-SO 2 -R 100 (or-S (= O) 2 -R 100 ) Having a substituent R 100 A sulfonyl group of (a). SubstitutionRadical R 100 It may be a group containing carbon atoms or a group containing no carbon atoms. At the substituent R 100 In the case of a group containing carbon atoms, the substituent R 100 The number of carbon atoms of (2) is 1 to 20, may be 1 to 10, and may be 1 to 7. Specific examples of the optionally substituted sulfonyl group having 0 to 20 carbon atoms include a sulfonamide group (= S) 2 -NH 2 ) Methanesulfonyl group, toluenesulfonyl group.
In the general formula (1), as represented by R 1 ～R 4 Among the "linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent" mentioned above, the "linear or branched alkyl group having 1 to 20 carbon atoms" includes, specifically, linear alkyl groups such as methyl, ethyl, n-propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl; and branched alkyl groups such as isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isooctyl group, and tert-octyl group.
In the general formula (1), as R 1 ～R 4 The "cycloalkyl group having 3 to 20 carbon atoms" in the "cycloalkyl group having 3 to 20 carbon atoms which may have a substituent" includes, specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, cyclododecyl and the like.
In the general formula (1), as R 1 ～R 4 Among the "linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent" mentioned above, the "linear or branched alkoxy group having 1 to 20 carbon atoms" includes, specifically, linear alkoxy groups such as methoxy, ethoxy, propoxy, n-butoxy, n-pentoxy, n-hexoxy, heptoxy, octoxy, nonoxy and decyloxy; and branched alkoxy groups such as isopropoxy, isobutoxy, sec-butoxy, tert-butoxy, isooctyloxy, and tert-octyloxy.
In the general formula (1), as represented by R 1 ～R 4 As the "cycloalkoxy group having 3 to 20 carbon atoms" in the "cycloalkoxy group having 3 to 20 carbon atoms which may have a substituent(s)" mentioned above, concrete examples thereof include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxyAnd the like.
In the general formula (1), as R 1 ～R 4 The "linear or branched alkenyl group having 2 to 20 carbon atoms" in the "linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent" includes, specifically, a vinyl group, an allyl group, an isopropenyl group, a 2-butenyl group, a 1-hexenyl group, or a linear or branched group in which a plurality of these alkenyl groups are bonded.
In the general formula (1), R 1 ～R 4 The "optionally substituted acyl group having 1 to 20 carbon atoms" is represented by the formula-C = O-R 101 The group shown. Substituent R 101 Either a group containing carbon atoms or a group containing no carbon atoms. At the substituent R 101 In the case of a group containing carbon atoms, the substituent R 101 The number of carbon atoms of (2) may be, for example, 1 to 20, or 1 to 10. The acyl group having 1 to 20 carbon atoms which may have a substituent may be a group in which an aromatic hydrocarbon group having 6 to 30 carbon atoms or a heterocyclic group having 5 to 30 carbon atoms in a ring is bonded through the acyl group. As substituents R 101 Examples thereof include-H and-CH 3 、-CH 2 CH 2 CH 3 、-CH＝CH 2 、-C 6 H 5 (-Ph). The "acyl group having 1 to 20 carbon atoms" in the "acyl group having 1 to 20 carbon atoms which may have a substituent" includes, specifically, formyl group, acetyl group, propionyl group, acryloyl group, benzoyl group and the like.
In the general formula (1), as represented by R 1 ～R 4 The "aromatic hydrocarbon group having 6 to 30 carbon atoms" in the "aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent" includes, specifically, phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyrenyl, and benzo [9,10] benzo]Phenanthryl, indenyl, fluorenyl, and the like. The "aromatic hydrocarbon group" in the present invention means an aromatic hydrocarbon group and a condensed polycyclic aromatic group, and among these, a phenyl group or a naphthyl group is preferable.
In the general formula (1), as represented by R 1 ～R 4 Wherein "the ring which may have a substituent(s) forms a heterocyclic group having 5 to 30 atoms"Examples of the heterocyclic group having 5 to 30 ring-forming atoms include pyridyl, pyrimidinyl, triazinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, quinolyl, isoquinolyl, naphthyridinyl, indolyl, benzimidazolyl, carbazolyl, carbolinyl, acridinyl, phenanthrolinyl, hydantoinyl, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, oxazolyl, benzoxazolyl, thiazolyl, and benzothiazolyl groups.
In the general formula (1), as represented by R 1 ～R 4 The "substituent" in the "substituted group" of the "amino group having 0 to 20 carbon atoms which may be substituted", "sulfonyl group having 0 to 20 carbon atoms which may be substituted", "linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted", "cycloalkyl group having 3 to 20 carbon atoms which may be substituted", "linear or branched alkoxy group having 1 to 20 carbon atoms which may be substituted", "cycloalkyloxy group having 3 to 20 carbon atoms which may be substituted", "linear or branched alkenyl group having 2 to 20 carbon atoms which may be substituted", "acyl group having 1 to 20 carbon atoms which may be substituted", "aromatic hydrocarbon group having 6 to 30 carbon atoms which may be substituted" or "heterocyclic group having 5 to 30 carbon atoms which may be substituted" may specifically be mentioned 3 - Nitro (-NO) 2 ) Nitroso group (-NO), cyano group (-CN), hydroxy group (-OH), -COO - A carboxyl group (-COOH), a thiol group (-SH),
An unsubstituted amino group; a mono-or di-substituted amino group having a linear or branched alkyl group having 1 to 17 carbon atoms or an aryl group having 6 to 24 carbon atoms, such as a methylamino group, dimethylamino group, diethylamino group, ethylmethylamino group, methylpropylamino group, di-t-butylamino group, diphenylamino group, etc.;
sulfonamide (-S (= O) 2 -NH 2 ) Examples of the substituent include a sulfonyl group (- = O) 2 -) of a group;
a linear or branched alkyl group having 1 to 17 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, an isohexyl group, a heptyl group, an n-octyl group, a tert-octyl group, an isooctyl group, a nonyl group, a decyl group, etc.;
cycloalkyl groups having 3 to 17 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl and cyclododecyl;
a straight-chain or branched alkoxy group having 1 to 17 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a tert-butoxy group, a n-pentyloxy group, or a n-hexyloxy group;
a cycloalkoxy group having 3 to 17 carbon atoms such as a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc.;
a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 1-pentenyl group, a 1-hexenyl group, an isopropenyl group, an isobutenyl group, or a linear or branched alkenyl group having 2 to 19 carbon atoms to which a plurality of these alkenyl groups are bonded;
acyl groups such as formyl, acetyl, propionyl, acryloyl, and benzoyl;
an aromatic hydrocarbon group having 6 to 24 carbon atoms such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a benzo [9,10] phenanthryl group, an indenyl group, a fluorenyl group, etc.;
pyridyl, pyrimidinyl, triazinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyrazinyl, pyridazinyl, piperidyl, piperazinyl, quinolyl, isoquinolyl, naphthyridinyl, indolyl, benzimidazolyl, carbazolyl, carbolinyl, acridinyl, phenanthrolinyl, phenanthridinyl, hydantoinyl, furyl, benzofuryl, dibenzofuryl, pyranyl, coumarinyl, isobenzofuryl, xanthenyl, pyranyl, thienyl, thiopyranyl, benzothienyl, dibenzothienyl, thioxanthyl, oxazolyl, benzoxazolyl, morpholinyl, thiazolyl, benzothiazolyl, and other heterocyclic groups having a ring shape of 5 to 24 atoms;
and a cyclic alkylene group having 3 to 24 carbon atoms such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, (1, 3-or 1, 4-) cyclohexadienyl group, 1, 5-cyclooctadienyl group and the like. These "substituents" may be contained in only 1 number, or may be contained in plural numbers, and in the case of containing plural numbers, they may be the same or different from each other. These "substituents" may have the substituents exemplified above, and these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
In the general formula (1), R 1 ～R 4 preferably-H, -SO 3 - 、-NO 2 An amino group having 0 to 10 carbon atoms which may have a substituent, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 10 carbon atoms which may have a substituent, or an acyl group having 1 to 10 carbon atoms which may have a substituent, more preferably-H, -SO 3 - 、-NO 2 Methyl, vinyl, or-N (CH) 3 ) 2 。
In the general formula (1), R 1 ～R 4 The above-mentioned substituents may form a ring by bonding adjacent groups to each other via a single bond, a bond (-O-) via an oxygen atom, or a bond (-S-) via a sulfur atom. For example, R 1 ～R 4 Between adjacent groups, which may be bonded to each other to form a benzene ring, R 1 And R 2 May be bonded to each other to form a benzene ring.
In the general formula (1), "M" represents a chromium atom (Cr), an iron atom (Fe), a cobalt atom (Co), a silicon atom (Si), or an aluminum atom (Al), preferably a Cr atom or a Co atom, more preferably a Cr atom.
In the general formula (1), "X" is a non-coloring cation, and specifically, a hydrogen ion (H) is mentioned + ) Lithium ion (Li) + ) Sodium ion (Na) + ) Potassium ion (K) + ) Such as alkali metal ions, cations containing organic compounds, and the like. Of these, alkali metal ions are more preferable, and K is particularly preferable + Or Na + 。
k represents the number of non-chromogenic cations "X" and represents an integer of 1 to 8, preferably an integer of 3 to 7.
In the general formula (1), "Y" represents "-O-" or "-O- (C = O) -", and when "O- (C = O) -" is represented, "M" is preferably bonded as in "M-O- (C = O) -".
In the general formula (1), "Z" is a 2-valent group represented by the following general formulae (2 a) to (2 k).
[ solution 7]
In the formula, R 5 ～R 47 Each independently represents-H, -SO 3 - 、-NO 2 、-NO、-CN、-OH、-COO - COOH, -SH, an amino group having 0 to 20 carbon atoms, a sulfonyl group having 0 to 20 carbon atoms, a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a linear or branched alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 carbon atoms, a linear or branched alkenyl group having 2 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heterocyclic group having 5 to 30 ring atoms, R 1 ～R 47 The amino group, sulfonyl group, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, alkenyl group, acyl group, aromatic hydrocarbon group, and heterocyclic group in (1) may have a substituent independently of each other or may have no substituent.
R 10 And R 11 、R 12 ～R 16 、R 17 ～R 21 、R 22 ～R 26 、R 27 And R 28 、R 29 ～R 34 、R 35 ～R 39 、R 40 ～R 45 And R 46 And R 47 Adjacent groups may be bonded to each other to form a ring.
R 5 ～R 47 May each independently be, for example, R 1 ～R 4 The groups exemplified in (1).
R 48 ～R 51 Each independently represents-H or-SO 3 - . A represents an oxygen atom or a sulfur atom. Wherein, 1 represents a bonding end with a nitrogen atom, and 2 represents a bonding end with an oxygen atom.
In the formula (2 a), R 6 preferably-COO - -COOH, a linear or branched C1-10 optionally having a substituentThe alkyl group or the acyl group having 1 to 10 carbon atoms which may have a substituent is preferably-COO - -COOH or methyl. In the formula (2 a), R 5 The alkyl group may have a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The group represented by formula (2 a) may be, for example, a group represented by the following formula (2 a').
[ solution 8]
In the formula (2 a'), R 5a ～R 5e Is represented by the formula 5 ～R 47 The same meaning as defined in (1). R 5a ～R 5e Adjacent groups may be bonded to each other to form a ring. Preferably R 5a ～R 5e Any 1 or 2 of them is-SO 3 - 、-NO 2 、-SO 2 NH 2 Or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent.
In the formula (2 b), R is preferred 7 Or R 8 Each independently represents-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and R is more preferably 7 And R 8 Each independently is-H, methyl or phenyl.
In the formula (2 c), R is preferred 9 ～R 11 Each independently represents-H, -CN, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and R is more preferably 9 Is ethyl, R 10 is-CN, R 11 Is a methyl group.
In the formula (2 d), R is preferred 12 ～R 16 Each independently represents-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
In the formula (2 e), R is preferred 17 ～R 21 Are respectively independentor-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
In the formula (2 f), R is preferred 22 ～R 26 Each independently represents-H, an amino group having 0 to 20 carbon atoms which may have a substituent, or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent.
In the formula (2 g), R is preferred 27 And R 28 Each independently represents-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or a linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent. R 31 And R 32 The ring may be bonded to form a ring, and when forming a ring, a 6-membered ring is preferable.
In the formula (2 h), R is preferred 29 ～R 34 Each independently represents-H or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, and more preferably all represent-H.
In the formula (2 i), R is preferred 35 ～R 39 Each independently represents-H or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, and more preferably-H or a methyl group.
In the formula (2 j), R is preferred 40 ～R 45 Any 1 or 2 of them is-SO 3 - or-COO - More preferably R 45 is-SO 3 - 。R 47 The amino group having 0 to 10 carbon atoms which may have a substituent is preferable, and-NH-is more preferable 2 。
In the formula (2 k), R is preferred 46 ～R 51 Any 1 or 2 of them is-SO 3 - or-COO - More preferably R 49 is-SO 3 - 。R 51 May be-H.
The compound represented by the general formula (1) includes all stereoisomers that can be produced, and all isomers can be preferably used as the compound of the present invention. For example, in the case where the compound represented by the following general formula (1-a) is present in the compound of the general formula (1), the compound of the present invention includes the compounds represented by the general formula (1) and the general formula (1-a), and may be a mixture of 2 or more kinds selected from these stereoisomers.
[ solution 9]
Specific examples of the compound of the present invention represented by the general formula (1) are shown in the following formulae, but the present invention is not limited thereto. In the exemplary compounds, the charge of the whole anion portion in the square bracket [ ] of the general formula (1) is described, and a part of the hydrogen atom is omitted in the structural formula.
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[ chemical No. 23]
[ formula 24]
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[ chemical 34]
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[ solution 45]
[ chemical formula 46]
[ solution 47]
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[ solution 51]
[ solution 52]
The compound (1) may be a compound represented by any one of formulae (3-1) to (13-4), and may be a compound represented by any one of formulae (3-1) to (5-1) or a compound represented by formula (3-17), (3-24), (4-1) or (5-1) from the viewpoints of more excellent light resistance and more excellent heat resistance.
An example of the method for producing the compound represented by the general formula (1) will be described below, but the method is not limited thereto. Specifically, first, a compound represented by the following general formula (II):
[ Hua 53]
[ in the formula (II), R 1 ～R 4 And Y represents the same meaning as defined above.]
An aromatic amine derivative having an appropriate substituent and/or a salt thereof is reacted with an alkaline aqueous solution prepared using sodium nitrite or the like in an aqueous acid solution such as hydrochloric acid, sulfuric acid or the like at an appropriate temperature to obtain an aromatic amine derivative represented by the following general formula (IV):
[ formula 54]
[ in the formula (IV), R 1 ～R 4 And Y represents the same meaning as defined above.]
The compound represented by (a) and/or a salt thereof (diazo component).
A salt (coupling agent component) of a compound represented by [ Z-OH ] or [ Z = O ] is obtained by dissolving a compound represented by the formula "Z-OH" or "Z = O" (described in detail later) in an aqueous solution of sodium hydroxide or the like and reacting the solution. "Z-OH" or "Z = O" can also be used directly as a coupler component.
Then, the diazo component is reacted with the coupler component (diazo coupling reaction) to obtain a compound represented by the following general formula and/or a salt thereof as an azo dye.
[ solution 55]
[ in the formula, R 1 ～R 4 Y and Z are as defined above.]
Next, by preparing a reaction liquid containing the above azo dye and an aqueous solution containing a compound containing an atom represented by M so as to become an atom (M): azo dye =1:2, reacting, complexing, salting out, and producing the compound (1) as 1: a type 2 complex salt compound. The compound containing an atom represented by M is a compound containing a Cr, fe, co, si or Al atom, and 1 kind of the compound may be used alone, or 2 or more kinds of the compounds may be used in combination. Specific examples of the compound containing an atom represented by M include chromium acetate.
The "Z-OH" or "Z = O" may be specifically any of compounds represented by the following general formulae (III-a) to (III-k).
[ solution 56]
[ wherein, R 5 ～R 51 And A represents the same meaning as defined above.]
The method for producing the compound represented by the general formula (1) according to the present embodiment includes: a step of reacting the compound represented by the general formula (I) with a compound containing Cr, fe, co, si or Al atoms to obtain a compound represented by the general formula (1).
The compound represented by the general formula (I) is obtained by diazo coupling reaction of a diazotized product obtained by diazotizing a compound represented by the above formula (II) and/or a salt thereof with a coupler component, which may be a compound represented by any one of the above general formulae (III-a) to (III-k) and/or a salt thereof.
The compound (1) can be purified by column chromatography; adsorption refining with silica gel, active carbon, activated clay, etc.; purification is carried out by a known method such as recrystallization from a solvent or crystallization. Identification of compounds and evaluation of physical properties can be performed by ultraviolet-visible absorption spectroscopy (UV-Vis), thermogravimetry-differential thermal analysis (TG-DTA), gas Chromatography (GC), nuclear magnetic resonance analysis (NMR), and the like.
The compound (1) can be used as a component of a dye composition. When 1 compound (1) is used alone, aluminum, fibers, and the like can also be colored. That is, the compound (1) can be preferably used as a dye compound for coloring aluminum, fiber, or the like by using 1 kind of monochromatic dye alone. In the compound (1), 2 or more species can be used in combination in order to obtain various colors by color mixing. For the dye composition, other components may be mixed for optimum dyeing (coloring using a dye). Specifically, there may be mentioned a liquid (solvent) such as water, alcohol, solvent and the like; additives such as surfactants, and the like. As the solvent, water is preferred. The compound (1) may be used as a component of a dye composition in combination with other pigments. The other coloring matter is a compound other than the compound (1), a pigment, a dye, or the like, and specific examples thereof include a ruthenium complex, a coumarin-based coloring matter, a cyanine-based coloring matter, a merocyanine-based coloring matter, a rhodamine-based coloring matter, a phthalocyanine-based coloring matter, a porphyrin-based coloring matter, a xanthene-based coloring matter, and the like. When the compound (1) is used in combination with other components, the amount of the other components to be used is preferably 10 to 200% by mass, more preferably 20 to 100% by mass, based on the compound (1).
The dye composition according to the present embodiment can be used as a colorant for anodized aluminum. When the compound (1) is used as a colorant for anodized aluminum or the like, the concentration of the compound (1) in the dye composition containing the compound (1) in the coloring (dyeing) method is preferably 0.02 to 10% by mass, more preferably 0.05 to 1% by mass, based on the total amount of the dye composition.
Among them, the anodized aluminum refers to aluminum which has been treated with an electrolytic solution such as an acid aqueous solution to form an oxide layer having pores on the surface of the electrolytically treated aluminum. The coloring agent for anodized aluminum means a coloring agent capable of coloring (dyeing) by adsorbing the compound (1) in the pores using a dye composition containing the compound (1) on the surface of the aluminum having pores. In general, in order to improve durability and light resistance of a colored aluminum surface, a sealing treatment for plugging pores is performed after coloring.
Examples of aluminum in the anodized aluminum include aluminum, aluminum oxide, aluminum alloys with other metals, and aluminum-containing metals or metal compounds.
As a coloring method of aluminum using a coloring agent for anodized aluminum, a known method can be used as an alumite dyeing method. For example, the methods described in japanese industrial standards (JIS H8601. The coloring method of aluminum is not particularly limited, and an example will be described below.
First, an aluminum plate is degreased with an acid aqueous solution such as sulfuric acid, oxalic acid, chromic acid, or sulfonic acid, and washed with water. Next, the degreased aluminum plate was used as an anode, and electrolysis was performed using an acid aqueous solution as an electrolyte, so that an anodized film (alumite film) having a large number of pores was formed on the surface of the aluminum anode (anodization treatment), and washing was performed with water. Next, after surface conditioning, washing with water, and the like are appropriately performed, the resultant is immersed in an aqueous colorant solution for anodized aluminum or the like containing a dye composition containing the compound of the present invention, and the dye is adsorbed in the pores (dyeing, electrolytic coloring), and the pores on the surface are sealed with an aluminum oxide hydrate or the like to form a sealing material, whereby coloring is possible.
When 2 or more kinds of the dye composition of the present invention are used in combination, or when the dye composition of the present invention is used in combination with another pigment, a mixed solution of all the pigments used may be prepared, anodized aluminum may be impregnated, and each of the pigment solutions may be prepared separately, and anodized aluminum may be impregnated in each solution sequentially.
The electrolysis conditions for coloring may be either direct current electrolysis or alternating current electrolysis, and direct current electrolysis is preferred. The current density is preferably 0.1 to 10A/dm 2 More preferably 0.5 to 3A/dm 2 . The energization time is preferably 10 seconds to 60 minutes. The thickness of the anodic oxide film is preferably 2 to 20 μm.
The treatment temperature in each step is preferably an appropriate temperature, and the temperature at the time of anodizing is preferably 0 to 80 ℃. The dyeing temperature is preferably 10 ℃ to 70 ℃. Other treatment temperatures are preferably 10 to 80 ℃.
The dye composition according to the present embodiment can be similarly used for an anodic oxide using a metal other than aluminum. For example, the dye can be applied to nonmetal such as conductive plastic as long as it can be adsorbed to anodized pores such as magnesium, zinc, titanium, and zirconium.
The coloring agent for anodized aluminum according to the present embodiment can be used to evaluate the characteristics of a sample colored with aluminum by measuring the hue, light resistance, heat resistance, and the like. The hue can also be evaluated visually for hue and uniformity, and can be determined as density (K/Sd) and hue (L) by a color difference meter ＊ 、a ＊ 、b ＊ ) And color difference (Δ E) ＊ ) To be measured.
The coloring agent for anodized aluminum according to the present embodiment can represent yellow, orange, red, peach, tea, bronze, a light color (e.g., light peach), or a shade different from that of a dark color. The coloring agent for anodized aluminum according to the present embodiment can also express a mixed color (intermediate colors such as yellow red, orange, red, violet, green, yellow green, dark cyan, black, gray, tea, gold, bronze, and the like) by using the above-mentioned compound in combination with other pigments. As the intermediate color, black or gray is preferable.
The light resistance test of aluminum colored with the coloring agent for anodized aluminum according to the present embodiment can be evaluated by irradiating a sample with light for a certain period of time using a tester or the like simulating sunlight including ultraviolet light, and measuring the change in hue of the colored aluminum before and after the test with a colorimeter or the like. In the judgment of light fastness, the judgment of fastness of dyeing by visual observation using a gray scale can be carried out by a method for determining the hue of colored aluminum in accordance with the japanese industrial standard (gray scale for discoloration and fading, JIS L0804).
Examples of the heat resistance test of aluminum colored by using the coloring agent for anodized aluminum according to the present embodiment include a method of heating for a certain time in a thermostat or a hot air dryer at a temperature range of 50 to 300 ℃ for 30 minutes to 50 hours or the like, and a method of evaluating a change in hue before and after the test in the same manner as the light resistance test.
The colored aluminum using the coloring agent for anodized aluminum according to the present embodiment is used for various aluminum plate materials, aluminum exterior materials, and the like.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples.
Synthetic example 1: synthesis of Compound (3-1)
(preparation of diazo component liquid)
8.7g of 2-amino-4-methylphenol, 120mL of water and 9.0g of 98% sulfuric acid were placed in a reaction vessel. While stirring the resulting reaction solution at 0 ℃, 4.9g of a 40 mass% aqueous solution of sodium nitrite was added dropwise, and then the mixture was reacted for 2 hours to obtain a diazo component solution.
(preparation of coupler composition liquid)
In a reaction vessel, 20.1g of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one, 150mL of water, and 6.4g of a 48 mass% aqueous solution of sodium hydroxide were placed, and the mixture was stirred at 10 ℃ for 2 hours to obtain a coupling agent component solution.
(diazo coupling)
The diazo component liquid was added to the stirring coupler component liquid, and the mixture was stirred for 18 hours to carry out a diazo coupling reaction. The completion of the reaction was confirmed by Thin Layer Chromatography (TLC). The purity of the product was confirmed by High Performance Liquid Chromatography (HPLC) based on the observed peak position and area of the retention time of a typical azo dye.
(Complex salt formation)
The reaction solution after the completion of the coupling was filtered, and the solid obtained by filtration and 200mL of water were placed in a reaction vessel to disperse the solid in water. 3.5g of chromium acetate was added to the dispersion, and the mixture was stirred at 95 ℃ for 10 hours. TLC was used to confirm the end of the reaction. The reaction solution was cooled to 25 ℃ and 20g of common salt was added thereto to carry out salting out, and then the reaction solution was filtered. The solid obtained by filtration was dried under reduced pressure to obtain a compound represented by the formula (3-1) (compound (3-1)) (32.1 g, yield: 100%) as a solid powder.
Synthetic example 2: synthesis of Compound (3-7)
(preparation of diazo component liquid)
9.8g of 2-amino-4-nitrophenol, 180mL of water, and 9.3g of 35% hydrochloric acid were placed in a reaction vessel. While the resulting reaction solution was stirred at 0 ℃, 10.8g of a 40 mass% sodium nitrite aqueous solution was added dropwise and reacted for 2 hours to obtain a diazo component solution.
(preparation of coupler composition liquid)
16.5g of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one, 180mL of water, and 12.6mL of a 48 mass% aqueous solution of sodium hydroxide were placed in a reaction vessel, and the mixture was stirred at 10 ℃ for 2 hours to obtain a coupling agent component solution.
(diazo coupling)
The diazo component solution was added to the stirring coupler component solution, and the mixture was stirred for 18 hours to carry out the diazo coupling reaction. The completion of the reaction was confirmed by Thin Layer Chromatography (TLC). The purity of the product was confirmed by High Performance Liquid Chromatography (HPLC) based on the observed peak position and area of the retention time of a typical azo dye.
(Complex salt formation)
The reaction solution after the coupling was filtered, and the solid obtained by filtration and 200mL of water were placed in a reaction vessel to disperse the solid in water. 7.3g of chromium acetate was added to the dispersion, and the mixture was stirred at 95 ℃ for 10 hours. TLC was used to confirm the completion of the reaction. The reaction solution was cooled to 25 ℃ and 20g of common salt was added thereto to carry out salting out, and then the reaction solution was filtered. The solid collected by filtration was dried under reduced pressure to obtain a compound represented by the above formula (3-7) (30.0 g, yield: 98.9%) as a solid powder.
Synthetic example 3: synthesis of Compound (3-2)
Compound (3-2) was obtained in the same manner as in synthesis example 1, except that 3-amino-4-hydroxybenzenesulfonic acid was used instead of 2-amino-4-methylphenol and 3-methyl-1- (4-sulfophenyl) -5-pyrazolone sodium was used instead of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component solution.
Synthetic example 4: synthesis of Compound (3-3)
A compound (3-3) was obtained in the same manner as in synthesis example 1, except that 2-amino-4-nitrophenol was used instead of 2-amino-4-methylphenol and 3-carboxy-1- (4-sulfophenyl) -5-pyrazolone sodium was used instead of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component solution, and sodium acetate was added instead of salt in the complex salting out.
Synthetic example 5: synthesis of Compounds (3-4) and (3-5)
Compound (3-4) or (3-5) was obtained in the same manner as in synthesis example 1, except that 3-amino-4-hydroxybenzenesulfonic acid or 3-amino-2-hydroxy-5-nitrobenzenesulfonic acid was used in place of 2-amino-4-methylphenol, and 3-methyl-1- (3' -sulfonamidophenyl) -5-pyrazolone was used in place of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in preparation of the coupler component liquid.
Synthetic example 6: synthesis of Compound (3-6)
Compound (3-6) was obtained in the same manner as in synthesis example 1, except that 3-amino-2-hydroxy-5-nitrobenzenesulfonic acid was used in place of 2-amino-4-methylphenol in the preparation of the diazo component solution, and 3-carboxy-1- (4-sulfophenyl) -5-pyrazolone sodium was used in place of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component solution.
Synthetic example 7: synthesis of Compound (3-17)
Compound (3-17) was obtained in the same manner as in synthesis example 1, except that 2-amino-4-nitrophenol was used in place of 2-amino-4-methylphenol in the preparation of the diazo component liquid, and 3-carboxy-1- (4-sulfophenyl) -5-pyrazolone sodium was used in place of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component liquid.
Synthetic example 8: synthesis of Compound (3-24)
Compound (3-24) was obtained in the same manner as in synthesis example 1, except that 1-amino-2-naphthol-4-sulfonic acid was used in place of 2-amino-4-methylphenol in the preparation of the diazo component liquid and 1, 3-dimethyl-5-pyrazolone was used in place of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component liquid.
Synthetic example 9: synthesis of Compound (4-1)
Compound (4-1) was obtained in the same manner as in synthesis example 1, except that 3-amino-4-hydroxybenzenesulfonic acid was used instead of 2-amino-4-methylphenol and barbituric acid was used instead of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component solution.
Synthetic example 10: synthesis of Compounds (4-2) to (4-4) ]
Compounds (4-2) to (4-4) were obtained in the same manner as in synthesis example 1, except that 3-amino-4-hydroxybenzenesulfonic acid or nitramine acid (3-amino-2-hydroxy-5-nitrobenzenesulfonic acid) was used instead of 2-amino-4-methylphenol, and barbituric acid or 1, 3-dimethylbarbituric acid was used instead of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component liquid.
Synthetic example 11: synthesis of Compound (5-1)
Compound (5-1) was obtained in the same manner as in synthesis example 1, except that 3-amino-4-hydroxybenzenesulfonic acid was used in place of 2-amino-4-methylphenol in the preparation of the diazo component liquid, and 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone was used in place of 3-methyl-1- (4-sulfophenyl) -2-pyrazolin-5-one in the preparation of the coupler component liquid.
< evaluation of hue and light fastness >
[ example 1]
Colored aluminum was produced by anodizing an aluminum substrate in the following steps. In the anodizing and dyeing steps, 2 kinds of dyeing conditions were set so that the treatment time and the concentration of the dye compound were changed.
(degreasing) A mixture of 150mL of a degreasing agent (manufactured by Aoye pharmaceutical industries, ltd. \124881248312503100), 70mL of 98% sulfuric acid, and 1000mL of water was prepared as a degreasing solution in a vessel, and the degreasing solution was prepared by immersing a dyed aluminum substrate cut to an appropriate size in the degreasing solution, degreasing the substrate at 60 ℃ for 3 minutes, and washing the degreased substrate with water.
(anodic oxidation) Using 98% sulfuric acid, 180g/L of an electrolyte was prepared, an aluminum substrate was connected to an electrode of an electrolytic device, immersed in an electrolyte bath at a temperature of 20. + -. 1 ℃ and a current density of 1.0A/dm 2 And anodizing under the condition of the following energization time to obtain an anodized film having the following thickness. After oxidation, water washing is carried out.
Dyeing conditions (1): anodic oxidation film thickness after electrification for 15 minutes: 5 μm
Dyeing conditions (2): anodic oxidation film thickness after 45 minutes of energization: 15 μm
(surface conditioning) A surface conditioning solution having a concentration of 50mL/L was prepared using a surface conditioning agent (TAC \12477125101254012523121, manufactured by Oye pharmaceutical industries, ltd.) and water, and the aluminum substrate was immersed at 45 ℃ for 1 minute. After dipping, the aluminum substrate is washed with water.
(dyeing) As a dye, using the compound (A-1) obtained in Synthesis example 1, as a dye composition of the present invention, aqueous solutions for dyeing containing the following dyes in the concentrations were prepared, and while being immersed in the following dyeing time, the dyes were dyed at a temperature of 55 ℃. And washing the aluminum substrate with water after dyeing.
Dyeing conditions (1): pigment concentration 0.1 wt% dyeing time: 30 seconds
Dyeing conditions (2): pigment concentration 0.2 wt% dyeing time: 5 minutes
(hole sealing) using a hole sealing agent (125831250312571298, manufactured by aoye pharmaceutical industry co., ltd. \ 12488, 12523H-298) and water, preparing 40mL/L of a hole sealing solution, and performing hole sealing treatment at about 90 ℃ for 15 minutes. After hole sealing treatment, drying with warm air.
(hue evaluation) the hue of the colored aluminum plate colored with the compound (3-1) was evaluated by visual observation. The evaluation results are shown in table 1.
(light resistance test) A light resistance test was carried out on a colored aluminum plate colored with the compound (3-1) by the following method. For the application of the Xenon gas fader/ATLAS Ci3000+ Xenon Weather Ometer (manufactured by the company: 124501248812521\\12473: 300-400 nm, 60W/m 2 Temperature in the test tank: 38 ℃ and humidity: 50%, blackboard (BP) temperature: the colored aluminum plate was irradiated at 63 ℃ for 50 hours, and the visual judgment of the color fastness was made in accordance with the gradation number (gradation for discoloration and fading, JIS L0804). The number of levels was the highest at 5 and the lowest at 1, and the higher the number of levels, the darker the color was indicated, and the hue before irradiation was maintained. In the evaluation method of the present invention, the results of the determination of the number of steps were classified into 3 steps, and the results are collectively shown in table 1 by the following evaluation criteria.
And (3) gray level judgment standard: the number of stages corresponds to the evaluation (A, B, C) in the present invention
Grade 5 to grade 4: a (particularly good lightfastness)
And 3, level: b (light resistance of normal level)
Grade 2 is as follows: c (light resistance low)
[ examples 9 to 15]
Colored aluminum plates were produced in the same manner as in example 1 except that the compounds shown in Table 2 were used as the colorants instead of the compound (3-1), and the hue and light resistance were evaluated. The measurement results are shown in table 2.
Comparative examples 1 to 5
As the dye, acid red 182, 183, 362, TAC Orange LH (301) (product of ohu pharmaceutical industry co., ltd.), TAC Orange CH (302) (product of ohu pharmaceutical industry co., ltd.) which is a known Orange type alumite dye that does not belong to the present invention and can be used in a single color, such as the following formula, was used in place of the compound (3-1), and hue and light resistance were evaluated in the same manner as in example 1, and the results are shown in table 2.
[ solution 57]
[ Table 1]
From the results shown in table 2, by using the anodized aluminum colorant composed of the dye composition containing the compound of the present invention, a coating film having high light resistance can be formed on aluminum in an orange color system such as yellow, orange, red, etc. On the other hand, the film using the pigment of comparative example was inferior in light resistance.
< evaluation of Heat resistance >
(Heat resistance test)
A heat resistance test was performed on the colored aluminum plate (example 9) colored under the dyeing conditions (2) of the above examples using the compounds (3 to 17) by the following method. The sample was heated using a constant temperature drier (model 87LEOP-450V manufactured by 12450124741252712531.
Temperature and heating time in the dryer: 200-5 hours, 250-3 hours
The method for evaluating heat resistance of the present invention measures the color difference of a colored aluminum sample before and after heating using the color difference meter described below, and evaluates the color difference visually using the following criteria. The results are shown in table 2.
The device comprises the following steps: color difference meter (Kenica Meinengda type spectral color difference meter CM-3700A)
Color difference: delta E ＊ ab (L ＊ a ＊ b ＊ CIE 1976) and. DELTA.E ＊ 00 (CIE DE2000)
Viewing angle: 10 degree
Heat resistance determination criteria:
a: good heat resistance (no discoloration nor fading)
B: usual level of heat resistance (no discoloration, but slight discoloration)
C: low heat resistance (discoloration and fading)
A heat resistance test was carried out in the same manner as in example 9 except that (5-1) was used in place of the compound (3-17). The results are summarized in table 2.
Comparative examples 1 to 3
A heat resistance test was performed in the same manner as in example 9, except that Acid Red 182, 183, or 362 of the above formula, which is a conventional orange-based dye, was used instead of compound (3-17). The results are summarized in table 2.
[ Table 2]
From the results shown in table 2, a coating having high heat resistance can be formed on aluminum in an orange color system by using an anodized aluminum colorant comprising a dye composition containing the compound of the present invention. The heat resistance of the coating film using the pigment of the example was not inferior to that of the coating film using the conventional orange-based pigment.
Industrial applicability
The dye composition containing the compound according to the present invention can provide a colorant for anodized aluminum capable of forming a monochromatic orange-based colored coating film having excellent light resistance. Further, by using this colorant, an anodized aluminum coating film which is orange in monochromatic coloration and excellent in light resistance can be obtained. The colored film obtained using the dye composition containing the compound according to the present invention is also excellent in heat resistance.
Claims (8)
1. A compound represented by the following general formula (1):
in the formula (1), the reaction mixture is,
R 1 ～R 4 each independently represents-H, -SO 3 - 、-NO 2 、
An amino group having 0 to 10 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 10 carbon atoms which may have a substituent, or,
An acyl group having 1 to 10 carbon atoms which may have a substituent,
R 1 ～R 4 adjacent groups may be bonded to each other to form a ring,
m represents Cr, fe, si or Al atom,
x represents a non-chromogenic cation, k represents an integer of 1 to 8,
y represents-O-or-O- (C = O) -,
z represents a group represented by the following general formula (2 a) or (2 b),
in the formula (I), the compound is shown in the specification,
R 5 and R 7 ～R 8 Each independently represents-H, -SO 3 - 、-NO 2 、-NO、-CN、-OH、-COO - 、-COOH、-SH、
An optionally substituted amino group having 0 to 20 carbon atoms,
A C0-20 sulfonyl group which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkyl group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkoxy group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
An optionally substituted acyl group having 1 to 20 carbon atoms,
An optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or
A heterocyclic group having 5 to 30 atoms in the ring which may have a substituent(s),
R 6 represents a methyl group, -COO - or-COOH, or a group of compounds selected from,
a represents an oxygen atom or a sulfur atom,
and, n 1 represents a bonding end to a nitrogen atom, and n 2 represents a bonding end to an oxygen atom.
2. A compound represented by the following general formula (1):
in the formula (1), the reaction mixture is,
R 1 and R 3 ～R 4 Each independently represents-H, -SO 3 - 、-NO 2 、
An optionally substituted amino group having 0 to 10 carbon atoms,
A linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 10 carbon atoms which may have a substituent, or,
An acyl group having 1 to 10 carbon atoms which may have a substituent,
R 2 represents-SO 3 - ，
R 1 ～R 4 Adjacent groups may be bonded to each other to form a ring,
m represents Cr, fe, si or Al atom,
x represents a non-chromogenic cation, k represents an integer of 1 to 8,
y represents-O-or-O- (C = O) -,
z represents a group represented by the following general formula (2 c),
in the formula (I), the compound is shown in the specification,
R 9 ～R 11 each independently represents-H, -SO 3 - 、-NO 2 、-NO、-CN、-OH、-COO - 、-COOH、-SH、
An amino group having 0 to 20 carbon atoms which may have a substituent,
A C0-20 sulfonyl group which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkyl group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 1 to 20 carbon atoms which may have a substituent,
A cycloalkoxy group having 3 to 20 carbon atoms which may have a substituent,
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
An optionally substituted acyl group having 1 to 20 carbon atoms,
An optionally substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or
A heterocyclic group having 5 to 30 atoms which may have a substituent(s),
R 10 and R 11 May be bonded to each other to form a ring,
and, n 1 represents a bonding end to a nitrogen atom, and n 2 represents a bonding end to an oxygen atom.
3. The compound according to claim 1 or 2, wherein,
in the above general formulae (2 a) to (2 c),
R 5 is a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
R 7 or R 8 Each independently represents-H, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,
R 9 ～R 11 each independently represents-H, -CN, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
4. A dye composition comprising a compound according to any one of claims 1 to 3.
5. A colorant for anodized aluminum, which contains the dye composition according to claim 4.
6. A method for coloring an anodized aluminum, an anodized aluminum oxide, or an anodized aluminum alloy, characterized by using a dye composition containing 0.02 to 10 mass% of the compound according to any one of claims 1 to 3.
7. A method of manufacturing the compound of any one of claims 1-3, comprising: a step of reacting a compound represented by the following general formula (I) with a compound containing a Cr, fe, si or Al atom to obtain a compound represented by the general formula (1),
in the formula (I), R 1 ～R 4 Y and Z are as defined in any one of claims 1 to 3.
8. The production process according to claim 7, wherein the compound represented by the general formula (I) is obtained by diazo coupling reaction of a diazotized product obtained by diazotizing a compound represented by the following formula (II) and/or a salt thereof with a coupler component:
in the formula (II), R 1 ～R 4 And Y represents the same meaning as defined in claim 7,
the coupling agent component is a compound represented by any one of the following general formulae (III-a) to (III-c) and/or a salt thereof:
in the formula, R 5 ～R 11 And A represents the same meaning as defined in claim 7.
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| PCT/JP2019/012921 WO2019189211A1 (en) | 2018-03-27 | 2019-03-26 | Complex salt compound, dye composition, coloring agent and coloring method for anodic aluminum oxide, and method for producing said compound |
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| JP7219755B2 (en) | 2023-02-08 |
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| KR20200135327A (en) | 2020-12-02 |
| WO2019189209A1 (en) | 2019-10-03 |
| TW201942256A (en) | 2019-11-01 |
| JP7219754B2 (en) | 2023-02-08 |
| CN111902489A (en) | 2020-11-06 |
| TW201942257A (en) | 2019-11-01 |
| JPWO2019189211A1 (en) | 2021-03-18 |
| WO2019189211A1 (en) | 2019-10-03 |
| KR20200135779A (en) | 2020-12-03 |
| TWI809069B (en) | 2023-07-21 |
| CN111971347A (en) | 2020-11-20 |
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