BE569789A - - Google Patents

Info

Publication number

BE569789A

BE569789A BE569789DA BE569789A BE 569789 A BE569789 A BE 569789A BE 569789D A BE569789D A BE 569789DA BE 569789 A BE569789 A BE 569789A

Authority

BE

Belgium

Prior art keywords

amino

dyes

copper

ortho

acid

Prior art date

Links

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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