DE542801C - Process for the production of real Kuepen dyes - Google Patents
Process for the production of real Kuepen dyesInfo
- Publication number
- DE542801C DE542801C DEI38801D DEI0038801D DE542801C DE 542801 C DE542801 C DE 542801C DE I38801 D DEI38801 D DE I38801D DE I0038801 D DEI0038801 D DE I0038801D DE 542801 C DE542801 C DE 542801C
- Authority
- DE
- Germany
- Prior art keywords
- real
- production
- dye
- carboxylic acid
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000975 dye Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 2
- -1 carboxylic acid halides Chemical class 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000984 vat dye Substances 0.000 description 3
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000012493 hydrazine sulfate Substances 0.000 description 2
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GMEOKIXCQPIWEK-UHFFFAOYSA-N 2-chloro-9,10-dioxoanthracene-1-carbonyl chloride Chemical compound ClC1=C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)C(=O)Cl GMEOKIXCQPIWEK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ACPOUJIDANTYHO-UHFFFAOYSA-N anthra[1,9-cd]pyrazol-6(2H)-one Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=NNC2=C1 ACPOUJIDANTYHO-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Eierstellung von echten Küpenfarbstoffen In dem hauptpatent ist ein Verfahren zur Herstellung von echten Küpenfarbstofien beschrieben, das darin besteht, daß man Pyrazolanthron-2-carbonsäurehalogenide und deren N A1kyl- bzw. h' Aralkylderivate mit solchen verküpbaren cyclischen Diketonen, die mindestens eine freie Aminogruppe enthalten, kondensiert.Process for egg production from real vat dyes In the main patent a process for the production of real vat dyes is described, which therein consists that one pyrazolanthrone-2-carboxylic acid halides and their N A1kyl- or h 'aralkyl derivatives with those cyclic diketones which can be linked to at least contain a free amino group, condensed.
Es wurde nun die bemerkenswerte Beobachtung gemacht, daß man zu gleichen bzw. analogen Produkten auch gelangen kann, wenn man i - Halogenanthrachinoncarbonsäurehalogenide mit den in dem Hauptpatent als Ausgangsprodukte benutzten Aminoderivaten kondensiert und die erhaltenen Kondensationsprodukte mit Hydrazin in Reaktion bringt. Auffallenderweise tritt in den meisten Fällen, ohne daß intermediäre Bildung eines Zwischenproduktes beobachtet werden kann, sofort der Ringschluß zum Pyrazolanthronderivat ein. Die Ausführung des Verfahrens erfolgt in der Weise, daß man die Chloranthrachinoncarbonsäurechlorid - Kondensationsprodukte, am besten in einem geeigneten Lösungsmittel, wie Pyridin, oder auch in wässeriger Anschlämmung unter Druck mit Hydrazinhydrat oder mit Hydrazinsulfat unter Zusatz der nötigen Menge Alkali erhitzt. Verwendet man die Produkte, die aus i - Chloranthrachinon-2-carbonsäurehalogenid hergestellt sind, so erhält man die gleichen Farbstoffe, wie im Hauptpatent beschrieben sind. Geht man dagegen von isomeren i-Halogenanthrachilioncarbonsäurehalogeniden aus, wie beispielsweise vom i-Chloranthrachinon-4.-carbonsäurechlorid, so ist auch auf diese das vorliegende Verfahren anwendbar, und man gelangt ebenfalls zu echten Küpenfarbstofien.The remarkable observation has now been made that one is too like or analogous products can also be achieved if i - halogenanthraquinone carboxylic acid halides condensed with the amino derivatives used as starting materials in the main patent and the condensation products obtained are reacted with hydrazine. Strikingly occurs in most cases without any intermediate formation of an intermediate can be observed, immediately the ring closure to the pyrazolanthrone derivative. the The process is carried out in such a way that the chloranthraquinone carboxylic acid chloride is used - condensation products, preferably in a suitable solvent such as pyridine, or in an aqueous suspension under pressure with hydrazine hydrate or with hydrazine sulfate heated with the addition of the necessary amount of alkali. One uses the products that are made out i - chloranthraquinone-2-carboxylic acid halide are produced, the same dyes as described in the main patent. If, on the other hand, one proceeds from isomers i-Halogenanthrachilioncarbonsäurehalogeniden from, such as from i-Chloranthraquinone-4.-carboxylic acid chloride, so the present method can also be applied to these, and one arrives as well to real vat dyes.
Beispiel i io kg i-Chlor-2-anthrachinoncarbonsäurea-anthrachinonamid werden in i oo kg wasserfreiem Pyridin am Rückfiuß erhitzt und 3 kg Hydr azinhydrat zutropfen gelassen. Nach kurzem Kochen wird der entstandene Farbstoff abgesaugt und mit Sprit nachgewaschen. Er ist identisch mit dem des Beispiels i des Hauptpatents. Durch Behandeln mit geeigneten Mitteln, z. B. durch Kochen mit Chlorlaube, kann der Rohfarbstoff noch weiter gereinigt werden.Example 10 kg of i-chloro-2-anthraquinonecarboxylic acid a-anthraquinonamide are refluxed in 100 kg of anhydrous pyridine and 3 kg of hydrazine hydrate allowed to drip. After a short boil, the resulting dye is filtered off with suction and washed with fuel. It is identical to that of example i of the main patent. By treating with suitable means, e.g. B. by cooking with chlorine arbor can the raw dye can be further purified.
Beispiel 2 Geht man, analog wie im Beispiel i beschrieben, vom i-Chlor-2-anthracliinancarbonsäure _ t' - benzoylamino" 4' -anthrachinonamid aus, sö erhält .man einen Farbstoff, der identisch mit dem des Beispiels 3 des Hauptpatents ist.Example 2 If the procedure is analogous to that described in Example i, the i-chloro-2-anthraclinanecarboxylic acid is used _ t '- benzoylamino "4' -anthraquinonamide from, so you get a dye that is identical to that of Example 3 of the main patent.
Beispiel 3 io kg i-Chlor-z-anthrachinoncarbonsäurea-anthrachinonamid werden in Form einer feinen Paste in z 5o kg Wasser mit 5 kg Hydrazinsulfat und der nötigen Menge Alkali Stunden auf 13o° im Autoklaven erhitzt Der in Form gelbbrauner Flocken abgeschiedene Farbstoff ist identisch mit dem des Beispiels i .Example 3 10 kg of i-chloro-z-anthraquinonecarboxylic acid a-anthraquinonamide are in the form of a fine paste in z 50 kg of water with 5 kg of hydrazine sulfate and The necessary amount of alkali is heated to 130 ° in the autoclave for hours The flake deposited dye is identical to that of Example i.
Beispiel 4 io kg i-Chlor-4-anthrachinonca.rbonsäurea-anthrachinonamid werden in 5o kg Pyridin und 5o kg kylol mit 4 kg Hydrazinhydrat i/2 Stunde lang am RückfluB erhitzt. Hierauf wird der Farbstoff abfiltriert und ausgewaschen. Zwecks Reinigung wird der Farbstoff mit hochsiedenden Lösungsmitteln, wie z. B. Anilin, zum Sieden erhitzt. Der Farbstoff färbt Baumwolle aus weinroter Küpe in braunvioletten Tönen an, die nach dem Verhängen und Absäuern in ein Gelb übergehen.EXAMPLE 4 100 kg of i-chloro-4-anthraquinonecarboxylic acid a-anthraquinonamide are refluxed in 50 kg of pyridine and 50 kg of kylene with 4 kg of hydrazine hydrate for 1/2 hour. The dye is then filtered off and washed out. For the purpose of cleaning, the dye with high-boiling solvents, such as. B. aniline, heated to boiling. The dye stains cotton from a wine-red vat in brown-violet tones, which turn yellow after hanging and acidification.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38801D DE542801C (en) | 1929-07-24 | 1929-07-24 | Process for the production of real Kuepen dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38801D DE542801C (en) | 1929-07-24 | 1929-07-24 | Process for the production of real Kuepen dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE542801C true DE542801C (en) | 1932-02-03 |
Family
ID=7189884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI38801D Expired DE542801C (en) | 1929-07-24 | 1929-07-24 | Process for the production of real Kuepen dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE542801C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2447981A (en) * | 1945-10-18 | 1948-08-24 | Ici Ltd | Anthraquinone vat dyestuffs |
-
1929
- 1929-07-24 DE DEI38801D patent/DE542801C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2447981A (en) * | 1945-10-18 | 1948-08-24 | Ici Ltd | Anthraquinone vat dyestuffs |
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