BE521054A - - Google Patents

Info

Publication number

BE521054A

BE521054A BE521054DA BE521054A BE 521054 A BE521054 A BE 521054A BE 521054D A BE521054D A BE 521054DA BE 521054 A BE521054 A BE 521054A

Authority

BE

Belgium

Prior art keywords

mixture

parts

anthraquinone

bis

methylene

Prior art date

Links

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• 239000000203 mixture Substances 0.000 claims description 27
• 238000000034 method Methods 0.000 claims description 19
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
• 239000002184 metal Substances 0.000 claims description 13
• 229910052751 metal Inorganic materials 0.000 claims description 13
• 239000000984 vat dye Substances 0.000 claims description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 11
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 10
• CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 claims description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
• 239000000975 dye Substances 0.000 claims description 6
• -1 ester salt Chemical class 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
• 150000004056 anthraquinones Chemical class 0.000 claims description 5
• 229910000881 Cu alloy Inorganic materials 0.000 claims description 4
• 239000010941 cobalt Substances 0.000 claims description 4
• 229910017052 cobalt Inorganic materials 0.000 claims description 4
• 229910052802 copper Inorganic materials 0.000 claims description 4
• 239000010949 copper Substances 0.000 claims description 4
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 230000004913 activation Effects 0.000 claims description 3
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 229910052742 iron Inorganic materials 0.000 claims description 3
• 229910052759 nickel Inorganic materials 0.000 claims description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
• WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 claims 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 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
• 239000000843 powder Substances 0.000 description 9
• 238000003756 stirring Methods 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• NXYNTHCSPIVNNX-SAIUNTKASA-N leucoester Natural products CCCCCCCCCCCCCCCC(=CCOC(=O)CCC[C@H](C)CCC[C@H](C)CCC(C)C)C NXYNTHCSPIVNNX-SAIUNTKASA-N 0.000 description 6
• 238000001816 cooling Methods 0.000 description 5
• 229920000742 Cotton Polymers 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 229910001369 Brass Inorganic materials 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 239000010951 brass Substances 0.000 description 3
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 3
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 230000003213 activating effect Effects 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 150000002739 metals Chemical class 0.000 description 2
• PZNXLZZWWBSQQK-UHFFFAOYSA-N n-(5-benzamido-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1C(=O)C2=CC=C3)=CC=CC=1C(=O)C2=C3NC(=O)C1=CC=CC=C1 PZNXLZZWWBSQQK-UHFFFAOYSA-N 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 238000005185 salting out Methods 0.000 description 2
• QZKRKMRVWWGTRU-UHFFFAOYSA-N 1,3-dichloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=C(Cl)C=C3C(=O)C2=C1 QZKRKMRVWWGTRU-UHFFFAOYSA-N 0.000 description 1
• AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
• FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
• RFKYAMWZNODXTH-UHFFFAOYSA-N 2-amino-1,5-dibenzoylanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=C(C(=O)C=4C=CC=CC=4)C=CC=C3C(=O)C2=C1C(=O)C1=CC=CC=C1 RFKYAMWZNODXTH-UHFFFAOYSA-N 0.000 description 1
• GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• SFJBWZNTPHYOEH-UHFFFAOYSA-N cobalt Chemical compound [Co].[Co].[Co] SFJBWZNTPHYOEH-UHFFFAOYSA-N 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• VDCUNNJIPITONP-UHFFFAOYSA-N n-(5-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 VDCUNNJIPITONP-UHFFFAOYSA-N 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1