CH139680A - Process for the preparation of a nitrogenous vat dye. - Google Patents
Process for the preparation of a nitrogenous vat dye.Info
- Publication number
- CH139680A CH139680A CH139680DA CH139680A CH 139680 A CH139680 A CH 139680A CH 139680D A CH139680D A CH 139680DA CH 139680 A CH139680 A CH 139680A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- works
- mol
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 4
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 claims description 4
- WCTKUENARPWTAY-UHFFFAOYSA-N ac1l9mss Chemical compound OS(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000000446 fuel Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- VZMULMSIWMLZLC-UHFFFAOYSA-N 2-aminoanthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=C(N)C=C3C3=CC=C4C1=C32 VZMULMSIWMLZLC-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Darstellung eines stickstoffhaltigen Küpentar stoffes. Im Hauptpatent ist ein Verfahren zur Darstellung eines stickstoffhaltigen Küpen- farbstoffes beschrieben, bei dem man 1 Mal.
des durch Behandlung von Pyranthron mit Halogen in Chlorsulfonsäure erhältlichen Tetrahalogenpyranthrons mit 3 Mol. des durch Nitrieren von Dibenzanthron mit Sal petersäure in Nitrobenzol und, Reduktion der entstandenen Nitroverbindung erhältlichen Aminodibenzanthrons und 1 Mol. 1-Amino- anthrachinon umsetzt.
Es wurde nun gefunden, da.ss man einen neuen Küpenfarbstoff erhält, wenn man 1 Mol. Diha.l.ogendibenmanthron, erhältlich durch Halogenieren von Dibenzanthron in Chlorsulfonsäure, mit 1 Mol. 5-Amino-4'- benzoylamino. - 1 .
1' - anthrimidcarbazol und 1 Mol. 1-Aminoanthrachinon umsetzt. Die Kondensation führt man zweckmässig in hochsiedenden Verdünnungsmitteln und un ter Zusatz von säurebindenden Mitteln, wie Natriumacetat, aus. Vielfach ist es von Ver- teil, Katalysatoren, beispielsweise Kupfer - ver binc lungen, zuzusetzen.
Der neue Farbstoff löst sich in konzen trierter Schwefelsäure mit violetter Farbe und gibt mit alkalischer Hy dro.swlfisösung eine braunviolette Küpenlösung, aus der die pflanzliche Faser in grauen bis schwarzer., hervorragend echten Tönen gefärbt wird.
<I>Beispiel:</I> 6,2 Teile Dibromdibenzanthron (dar gestellt durch Bromieren von Dibenzan- thron in Chlorsulfansäure) werden in 250 Teilen Nitrobenzol mit 6,7 Teilen 5-Amino- 4'-benzoylamino-1.1'-anthrimidcarbazol, 2,3 Teilen 1-Aminoanthrachinon, 10 Teilen Na- triumacetat, 1,;
3 Teilen Kupferoxyd so lange gekocht, bis das Reaktionsprodukt praktisch bromfrei ist. Darauf wird in der üblichen Weise aufgearbeitet.
Method for the preparation of a nitrogenous Küpentar material. The main patent describes a process for the preparation of a nitrogen-containing vat dye, in which one is once.
of the tetrahalogenopyranthrone obtainable by treating pyranthrone with halogen in chlorosulfonic acid with 3 mol. of the aminodibenzanthrone and 1 mol. 1-amino anthraquinone obtainable by nitrating dibenzanthrone with nitric acid in nitrobenzene and reducing the resulting nitro compound.
It has now been found that a new vat dye is obtained if 1 mole. Diha.l.ogendibenmanthron, obtainable by halogenating dibenzanthrone in chlorosulfonic acid, with 1 mole. 5-Amino-4'-benzoylamino. - 1 .
1 '- anthrimidcarbazole and 1 mol. 1-Aminoanthraquinone converts. The condensation is expediently carried out in high-boiling diluents and with the addition of acid-binding agents such as sodium acetate. It is often advisable to add catalysts, for example copper compounds.
The new dye dissolves in concentrated sulfuric acid with a violet color and, with an alkaline hydrofluoric acid solution, gives a brown-violet vat solution from which the vegetable fibers are dyed in gray to black, extremely real shades.
<I> Example: </I> 6.2 parts of dibromodibenzanthrone (made by brominating dibenzanthrone in chlorosulfanic acid) are mixed with 6.7 parts of 5-amino-4'-benzoylamino-1.1'-anthrimide carbazole in 250 parts of nitrobenzene, 2.3 parts of 1-aminoanthraquinone, 10 parts of sodium acetate, 1;
3 parts of copper oxide are boiled until the reaction product is practically bromine-free. This is worked up in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE139680X | 1927-10-18 | ||
| CH138317T | 1928-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139680A true CH139680A (en) | 1930-04-30 |
Family
ID=25713132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139680D CH139680A (en) | 1927-10-18 | 1928-10-01 | Process for the preparation of a nitrogenous vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139680A (en) |
-
1928
- 1928-10-01 CH CH139680D patent/CH139680A/en unknown
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