BE534869A

BE534869A -

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Publication number: BE534869A
Authority: BE; Belgium
Prior art keywords: chromium; complex; atom; aquasolubilizing; monoazo
Prior art date

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English (en)

French (fr)

Publication of BE534869A publication Critical patent/BE534869A/fr

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239000000975 dye Substances 0.000 claims description 55
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 30
229910052804 chromium Inorganic materials 0.000 claims description 29
239000011651 chromium Substances 0.000 claims description 23
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 23
238000000034 method Methods 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
210000002268 Wool Anatomy 0.000 claims description 11
238000004043 dyeing Methods 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
150000001845 chromium compounds Chemical class 0.000 claims description 6
230000001264 neutralization Effects 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
230000002378 acidificating Effects 0.000 claims description 5
125000004429 atoms Chemical group 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004433 nitrogen atoms Chemical group N* 0.000 claims description 5
RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
150000001844 chromium Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000000987 azo dye Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
210000004940 Nucleus Anatomy 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000000835 fiber Substances 0.000 claims description 2
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical class CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 claims 1
241000699666 Mus <mouse, genus> Species 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000004532 chromating Methods 0.000 description 7
230000001808 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000007792 addition Methods 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
-1 2 -ethylphenyl Chemical group 0.000 description 2
QMZAQDOAQRVXOR-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-5-methyl-4H-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=C(C)C=CC=C1C QMZAQDOAQRVXOR-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
QDOXWKRWXJOMAK-UHFFFAOYSA-N Chromium(III) oxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N Citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical class O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
HHNWXQCVWVVVQZ-UHFFFAOYSA-N 2-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(N)=C1 HHNWXQCVWVVVQZ-UHFFFAOYSA-N 0.000 description 1
WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
GENSTRUCMIZOCD-UHFFFAOYSA-N 5-methyl-2-(2-methylphenyl)-4H-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1C GENSTRUCMIZOCD-UHFFFAOYSA-N 0.000 description 1
RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical class NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 1
IRHRJPWNOKKLJT-UHFFFAOYSA-N CC1=C(C(=CC=C1)OC)N1N=C(CC1=O)C Chemical compound CC1=C(C(=CC=C1)OC)N1N=C(CC1=O)C IRHRJPWNOKKLJT-UHFFFAOYSA-N 0.000 description 1
241000854350 Enicospilus group Species 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
229940069002 Potassium Dichromate Drugs 0.000 description 1
XMXNVYPJWBTAHN-UHFFFAOYSA-N Potassium chromate Chemical compound [K+].[K+].[O-][Cr]([O-])(=O)=O XMXNVYPJWBTAHN-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000000240 adjuvant Effects 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Chemical class 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atoms Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000875 corresponding Effects 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
XKUUMWKWUZRRPD-UHFFFAOYSA-N heptan-2-amine;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.CCCCCC(C)[NH3+].CCCCCC(C)[NH3+] XKUUMWKWUZRRPD-UHFFFAOYSA-N 0.000 description 1
239000010985 leather Substances 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
238000005185 salting out Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001187 sodium carbonate Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
230000001131 transforming Effects 0.000 description 1
FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1