DE520876C - Process for the production of Kuepen dyes - Google Patents
Process for the production of Kuepen dyesInfo
- Publication number
- DE520876C DE520876C DEI38457D DEI0038457D DE520876C DE 520876 C DE520876 C DE 520876C DE I38457 D DEI38457 D DE I38457D DE I0038457 D DEI0038457 D DE I0038457D DE 520876 C DE520876 C DE 520876C
- Authority
- DE
- Germany
- Prior art keywords
- production
- dyes
- vat
- kuepen dyes
- condensation product
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 title description 9
- 239000007859 condensation product Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000984 vat dye Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- DGJNWQJOASAMHY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)Cl)=CC=C3C(=O)C2=C1 DGJNWQJOASAMHY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000375 suspending agent Substances 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/40—Condensation products of benzanthronyl-amino-anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Küpenfarbstoffen =Nach dem Verfahren der Patentschrift :212471 werden Küpenfarbstoffe dadurch erhalten, daß man Bz-i-benzanthronyl-iaminoanthrachinon oder dessen Derivate mit alkalischen Kondensationsmitteln behandelt. Der beispielsweise nach diesem Verfahren aus Bz -i-benzanthrony l-i-amino- 5 -artndnoanthr achinon erhältliche Farbstoff, der aller Wahrscheinlichkeit nach folgende Konstitution hat: und der also in Alithrachinoli-5-Stellung noch eine: freie Aminogruppe trägt, färbt Baumwolle aus der Küpe in blaugrauen Tönen an. Es wurde null gefunden, daß sich aus diesem Kondensationsprodukt und seinen im Benranthronkern halogenierten Derivaten wertvolle neue Farbstoffe herstellen lassen, wenn man sie mit Säurehalogeniiden umsetzt. Die erhaltenen Farbstoffe sind ausgezeichnet durch ihre wertvolle olive Nünance und eine sehr gute Chlorechtheit.Process for the production of vat dyes = According to the process of patent specification: 212471, vat dyes are obtained by treating Bz-i-benzanthronyl-iaminoanthraquinone or its derivatives with alkaline condensing agents. The dye obtainable, for example, from Bz -i-benzanthrony li-amino-5 -artndnoanthr achinon by this process, which in all probability has the following constitution: and who thus still has a free amino group in the alithraquinoli-5-position, stains cotton from the vat in blue-gray tones. It has been found zero that valuable new dyes can be prepared from this condensation product and its derivatives halogenated in the benrant throne nucleus if they are reacted with acid halides. The dyes obtained are distinguished by their valuable olive nuance and very good fastness to chlorine.
Die Kondensation erfolgt schon beim einfachen Erhitzen der Komponenten in einem höher siedenden Lösungs- bzw. Suspensionsmittels mit oder ohne Zusatz eines säureb.indenlden Mittels.The condensation takes place as soon as the components are simply heated in a higher-boiling solvent or suspending agent with or without the addition of a acid-binding agent.
Verwendet man, als Ausgangsstoff Halogen-Bz-i-benz:anthronyl-i-a.nino- 5 -aminoan.thrachinon, so gelangt man zu den entsprechenden halogenierten Farbstoffen. Beispiel i d6 kg des Kondensationsproduktes, erhalt.eil nach dein Verfahren der Patentschrift 212 471 durch Behandlung von Bz-i-benzanthronyl-i-amitlo-5-arninoanthrachinoli init alkoholischem Kali, «-erden in 5oo kg Nitrobenzol mit 2o kg Benzoylchlori@d unter Rühren rückfließend gekocht. Nach etwa zwei Stunden läßt man erkalten und saugt den ausgeschiedenen Farbstoff ab und wäscht nach. Er löst sich in konzentrierter Schwefelsäure mit grüner Farbe und färbt aus blauvioletter Küpe Baumwolle in hervorragend echten, gelboliv en Tönen an.If the starting material used is halogen-Bz-i-benz: anthronyl-i-a.nino- 5 -aminoan.thraquinone, this leads to the corresponding halogenated dyes. Example i d6 kg of the condensation product, obtained according to your method of U.S. Patent 212,471 for the treatment of Bz-i-benzanthronyl-i-amitlo-5-arninoanthraquinoli with alcoholic potash in 500 kg nitrobenzene with 20 kg benzoylchloride refluxed with stirring. After about two hours it is allowed to cool and sucks off the precipitated dye and washes. He dissolves in more concentrated Sulfuric acid with green color and stains from blue-violet vat Cotton in extremely genuine, yellow-olive tones.
Bei Verwendung von Zimtsäurechlorid statt Benzoylchlorid erhält man den analogen Farbstoff von fast gleichen Eigenschaften. Die Kondensation läßt sich auch unter Zusatz von Pyr idin durchführen. Beispiele Wird das Kondensationsprodukt, erhalten durch Behandlung von 6-Chlor-Bz-i-benzanthront'l-i-amino-5-aminoanthrächinon mit alkoholischem Kali, nach Angaben des Beispiels i mit Benzoylcblori@d umgesetzt, so erhält man einen Farbstoff, der sich seinen Eigenschaften nach von dem in Beispiel i ahnten nur unwesentlich unterscheidet. Beispiel g 4.6 kg des gleichen Ausgangskörpers wie hei Beispiel i werden mit 30 kg Anthrachinon-2-carbonsäurechlärid ein bis zwei Stunden unter Rühren in Nitrobenzollösung bei Siedetemperatur gehalten. Nach Erkalten wird der ausgefallene Farbstoff abgeschieden und gewaschen. Seine Lösungsfarbe in Schwefelsäure ist grün. Mit Hydrosulfit und Lauge erhält man 'eine blaue Küpe, aus der Baumwolle in sehr echten, gelboliven Tönen angefärbt wird.When using cinnamic acid chloride instead of benzoyl chloride, the analogous dye is obtained with almost the same properties. The condensation can also be carried out with the addition of pyridine. EXAMPLES If the condensation product, obtained by treating 6-chloro-Bz-i-benzanthront'l-i-amino-5-aminoanthraquinone with alcoholic potassium, is reacted with benzoylcblori @ d as described in Example i, a dye is obtained which differs only insignificantly in terms of its properties from those in the example. Example g 4.6 kg of the same starting material as in Example i are kept at boiling temperature with 30 kg of anthraquinone-2-carboxylic acid chloride for one to two hours while stirring in nitrobenzene solution. After cooling, the precipitated dye is separated off and washed. Its solution color in sulfuric acid is green. With hydrosulphite and lye you get a blue vat from which cotton is dyed in very real, yellow-olive tones.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38457D DE520876C (en) | 1929-06-22 | 1929-06-22 | Process for the production of Kuepen dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38457D DE520876C (en) | 1929-06-22 | 1929-06-22 | Process for the production of Kuepen dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE520876C true DE520876C (en) | 1931-03-17 |
Family
ID=7189788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI38457D Expired DE520876C (en) | 1929-06-22 | 1929-06-22 | Process for the production of Kuepen dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE520876C (en) |
-
1929
- 1929-06-22 DE DEI38457D patent/DE520876C/en not_active Expired
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