BE482346A

BE482346A -

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Publication number: BE482346A
Authority: BE; Belgium
Prior art keywords: leuco; derivative; derivatives; parts; sulfuric
Prior art date

Application number

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English (en)

French (fr)

Publication of BE482346A publication Critical patent/BE482346A/fr

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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 13
-1 hydrocarbon radicals Chemical class 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
239000000975 dye Substances 0.000 claims description 11
150000003857 carboxamides Chemical class 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
239000001046 green dye Substances 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical group 0.000 claims description 2
230000019635 sulfation Effects 0.000 claims description 2
238000005670 sulfation reaction Methods 0.000 claims description 2
GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
229910052736 halogen Chemical group 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
239000000984 vat dye Substances 0.000 description 13
239000000243 solution Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
239000002585 base Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
239000011541 reaction mixture Substances 0.000 description 6
KNVLCWQKYHCADB-UHFFFAOYSA-N chlorosulfonyloxymethane Chemical compound COS(Cl)(=O)=O KNVLCWQKYHCADB-UHFFFAOYSA-N 0.000 description 5
239000004744 fabric Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920001353 Dextrin Polymers 0.000 description 3
239000004375 Dextrin Substances 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
235000019425 dextrin Nutrition 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
241000083869 Polyommatus dorylas Species 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000001350 alkyl halides Chemical group 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
AFDQGRURHDVABZ-UHFFFAOYSA-N n,n-dimethylformamide;sulfur trioxide Chemical compound O=S(=O)=O.CN(C)C=O AFDQGRURHDVABZ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1