BE523495A - - Google Patents

Info

Publication number

BE523495A

BE523495A BE523495DA BE523495A BE 523495 A BE523495 A BE 523495A BE 523495D A BE523495D A BE 523495DA BE 523495 A BE523495 A BE 523495A

Authority

BE

Belgium

Prior art keywords

group

chromium

atom

general formula

monoazo

Prior art date

Links

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• 239000000975 dye Substances 0.000 claims description 54
• 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 22
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 20
• 229910052804 chromium Inorganic materials 0.000 claims description 20
• 239000011651 chromium Substances 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 229910052751 metal Inorganic materials 0.000 claims description 13
• 239000002184 metal Substances 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 150000001875 compounds Chemical class 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 150000002739 metals Chemical class 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 150000001845 chromium compounds Chemical class 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 238000004043 dyeing Methods 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• 125000000565 sulfonamide group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
• 239000001257 hydrogen Substances 0.000 claims 2
• 229910052739 hydrogen Inorganic materials 0.000 claims 2
• 150000003839 salts Chemical class 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 238000005859 coupling reaction Methods 0.000 description 12
• 230000008878 coupling Effects 0.000 description 11
• 238000010168 coupling process Methods 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• 210000002268 wool Anatomy 0.000 description 9
• 239000011541 reaction mixture Substances 0.000 description 8
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• 238000009835 boiling Methods 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 5
• 150000008049 diazo compounds Chemical class 0.000 description 5
• 239000012535 impurity Substances 0.000 description 5
• KMXMLAGYNHELHA-UHFFFAOYSA-N 8-hydroxynaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 KMXMLAGYNHELHA-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 238000006193 diazotization reaction Methods 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 229910052500 inorganic mineral Inorganic materials 0.000 description 4
• 239000011707 mineral Substances 0.000 description 4
• 238000000926 separation method Methods 0.000 description 4
• 235000010288 sodium nitrite Nutrition 0.000 description 4
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 3
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
• YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 229910052802 copper Inorganic materials 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• LUVRKIGRHKKAOW-UHFFFAOYSA-N 1-(2,3-diamino-4-hydroxy-5-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC([N+]([O-])=O)=C(O)C(N)=C1N LUVRKIGRHKKAOW-UHFFFAOYSA-N 0.000 description 1
• WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
• ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 description 1
• SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
• WZSBYBXNPKFJTA-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C(O)C=C1[N+]([O-])=O WZSBYBXNPKFJTA-UHFFFAOYSA-N 0.000 description 1
• GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
• MICDVUDJBHIFHA-UHFFFAOYSA-N 4-amino-2,5-dimethoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(OC)C=C1N MICDVUDJBHIFHA-UHFFFAOYSA-N 0.000 description 1
• QKRGVQSQFKCZEC-UHFFFAOYSA-N 4-chloro-2,5-diethoxyaniline Chemical compound CCOC1=CC(Cl)=C(OCC)C=C1N QKRGVQSQFKCZEC-UHFFFAOYSA-N 0.000 description 1
• TZBROGJRQUABOK-UHFFFAOYSA-N 4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 TZBROGJRQUABOK-UHFFFAOYSA-N 0.000 description 1
• WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• -1 N-substituted amides Chemical class 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 230000001034 aminogenic effect Effects 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 238000004532 chromating Methods 0.000 description 1
• QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 239000010941 cobalt Substances 0.000 description 1
• 229910017052 cobalt Inorganic materials 0.000 description 1
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
• 230000027326 copulation Effects 0.000 description 1
• KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 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
• 230000002349 favourable effect Effects 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 229910052759 nickel Inorganic materials 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 235000021178 picnic Nutrition 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000010344 sodium nitrate Nutrition 0.000 description 1
• 239000004317 sodium nitrate Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 239000004753 textile Substances 0.000 description 1
• 238000005406 washing Methods 0.000 description 1