BE569789A

BE569789A -

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Publication number: BE569789A
Authority: BE; Belgium
Prior art keywords: amino; dyes; copper; ortho; acid
Prior art date

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English (en)

French (fr)

Publication of BE569789A publication Critical patent/BE569789A/fr

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239000000975 dye Substances 0.000 claims description 31
230000001808 coupling Effects 0.000 claims description 10
238000010168 coupling process Methods 0.000 claims description 10
238000005859 coupling reaction Methods 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
XYYUWIRXDRCWDO-UHFFFAOYSA-N NC1=C(C2=CC=C(C=C2C=C1)[N+](=O)[O-])S(=O)(=O)O Chemical class NC1=C(C2=CC=C(C=C2C=C1)[N+](=O)[O-])S(=O)(=O)O XYYUWIRXDRCWDO-UHFFFAOYSA-N 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
229910052802 copper Inorganic materials 0.000 claims description 7
239000010949 copper Substances 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
-1 nitroazo Chemical group 0.000 claims description 6
230000001590 oxidative Effects 0.000 claims description 6
230000001603 reducing Effects 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
YXFWFUSVDJIVIV-UHFFFAOYSA-N 4-nitro-2H-triazole Chemical class [O-][N+](=O)C=1C=NNN=1 YXFWFUSVDJIVIV-UHFFFAOYSA-N 0.000 claims description 3
239000000987 azo dye Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 2
239000000835 fiber Substances 0.000 claims description 2
150000002739 metals Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 17
239000002253 acid Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
229920000742 Cotton Polymers 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 5
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 5
PEFKYEIJIGWGBJ-UHFFFAOYSA-N 3-amino-7-nitronaphthalene-1,5-disulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 PEFKYEIJIGWGBJ-UHFFFAOYSA-N 0.000 description 4
239000005749 Copper compound Substances 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
150000001880 copper compounds Chemical class 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
239000008103 glucose Substances 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000003852 triazoles Chemical class 0.000 description 4
SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
FTBBGQKRYUTLMP-UHFFFAOYSA-N 2-nitro-1H-pyrrole Chemical compound [O-][N+](=O)C1=CC=CN1 FTBBGQKRYUTLMP-UHFFFAOYSA-N 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
PBTUTICKCLVZAB-ZJVSAGCXSA-H copper;tetrasodium;7-[[4-(2-hydroxyethylamino)-6-[[(6E)-6-[(2-oxido-5-sulfonatophenyl)hydrazinylidene]-5-oxo-7-sulfonatonaphthalen-2-yl]amino]-1,3,5-triazin-2-yl]amino]-3-[(4-methoxy-2-sulfonatophenyl)diazenyl]-4-oxidonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].[O-]S(=O)(=O)C1=CC(OC)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C([O-])C1=CC=C2NC1=NC(NCCO)=NC(NC=2C=C3C=C(C(=N/NC=4C(=CC=C(C=4)S([O-])(=O)=O)[O-])/C(=O)C3=CC=2)S([O-])(=O)=O)=N1 PBTUTICKCLVZAB-ZJVSAGCXSA-H 0.000 description 2
230000000875 corresponding Effects 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
230000001264 neutralization Effects 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000000843 powder Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
QWENRTYMTSOGBR-UHFFFAOYSA-N 1,2,3-triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 1
HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 description 1
DWGBLODXAMYUOP-UHFFFAOYSA-N 7-amino-3-nitronaphthalene-1-sulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 DWGBLODXAMYUOP-UHFFFAOYSA-N 0.000 description 1
GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
QHKNGLXQDLRMSX-UHFFFAOYSA-N CC(=O)NC1=C(Cl)C2=CC(=CC(O)=C2C=C1)S(O)(=O)=O Chemical compound CC(=O)NC1=C(Cl)C2=CC(=CC(O)=C2C=C1)S(O)(=O)=O QHKNGLXQDLRMSX-UHFFFAOYSA-N 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
239000001046 green dye Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
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 description 1
239000000203 mixture Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000003638 reducing agent Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000001187 sodium carbonate Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1