DE515331C - Process for the preparation of Kuepen dyes of the anthracene series - Google Patents
Process for the preparation of Kuepen dyes of the anthracene seriesInfo
- Publication number
- DE515331C DE515331C DEI37914D DEI0037914D DE515331C DE 515331 C DE515331 C DE 515331C DE I37914 D DEI37914 D DE I37914D DE I0037914 D DEI0037914 D DE I0037914D DE 515331 C DE515331 C DE 515331C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- weight
- parts
- preparation
- anthracene series
- 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
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
- C09B5/26—Carbazoles of the anthracene series
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Küpenfarbstoffen der Anthracenreihe Aus Anthrimiden werden durch Kondensation mit sauren oder alkalischen Mitteln Küpenfarbstoffe dargestellt, die Carbazolringe enthalten (vgl. beispielsweise die Patentschriften 251 021, 240 o8o, 251350, 249 000, 230 407). Aus diesen Rohprodukten werden nach der Patentschrift 430 559 und gemäß Patent 507 340 die Farbstoffe in reiner Form isoliert.Process for the preparation of vat dyes of the anthracene series From anthrimides, vat dyes containing carbazole rings are produced by condensation with acidic or alkaline agents (cf., for example, patents 251 021, 240 080, 251350, 249 000, 23 0 407). According to patent specification 430 559 and patent 507 340, the dyes are isolated in pure form from these crude products.
Es wurde nun gefunden, daß man durch Umsetzung der Halogenierungsprodukte der obengenannten Farbstoffe mit stickstoffhaltigen Verbindungen, die mindestens ein austauschfähiges Wasserstoffatom enthalten, zu neuen, einheitlichen und wertvollen Küpenfarbstoffen gelangt, die bei der gleichen hervorragenden Echtheit der Grundsubstanzen viel tiefer gefärbt sind. Beispiele 1. 65 Gewichtsteile des Dibromderivates des Farbstoffes gemäß Patent 507 340, Beispiel i (erhalten durch Bromierung in Chlorsulfonsäure bei Gegenwart von Jod), werden mit 5o Gewichtsteilen a - Aminoanthrachinon, 5o Gewichtsteilen Soda, io Gewichtsteilen Natriumacetat, i Gewichtsteil Kupferchlorür in iooo Gewichtsteilen Naphthalin 2 Tage gekocht. Die Schmelze wird mit Toluol verdünnt und heiß filtriert, der Rückstand mit Toluol gewaschen, dann mit Wasserdampf behandelt und getrocknet. Zur Entfernung von Nebenprodukten ist eine Behandlung mit Chlorlauge zweckmäßig. Das erhaltene schwarzbraune Pulver färbt aus der roten Hydrosulfitküpe ein echtes Khaki.It has now been found that by reacting the halogenation products of the above-mentioned dyes with nitrogen-containing compounds which contain at least one exchangeable hydrogen atom, new, uniform and valuable vat dyes are obtained which are much deeper colored with the same excellent fastness of the basic substances. EXAMPLES 1. 65 parts by weight of the dibromo derivative of the dye according to Patent 507 340, Example i (obtained by bromination in chlorosulfonic acid in the presence of iodine) are mixed with 50 parts by weight of α-aminoanthraquinone, 50 parts by weight of soda, 10 parts by weight of sodium acetate, 1 part by weight of copper chloride in 100 parts by weight Naphthalene boiled for 2 days. The melt is diluted with toluene and filtered hot, the residue is washed with toluene, then treated with steam and dried. Treatment with sodium chloride solution is expedient to remove by-products. The black-brown powder obtained turns the red hydrosulfite vat into a real khaki.
2. 8o Gewichtsteile des im Beispiel i genannten Bromderivates werden in i2oo Gewichtsteilen Naphthalin mit 5o Gewichtsteilen Soda, i Gewichtsteil Kupferchlorür, io Gewichtsteilen Natriumacetat und 8o Gewichtsteilen i-Amino-5-benzoylaminoanthrachinon 24 Stunden auf ?io° erhitzt. Die Schmelze wird wie in Beispiel i aufgearbeitet. Man erhält einen Farbstoff, der Baumwolle aus der Küpe schwarzbraun anfärbt.2. 80 parts by weight of the bromine derivative mentioned in Example i in i2oo parts by weight of naphthalene with 50 parts by weight of soda, i part by weight of copper chloride, 10 parts by weight of sodium acetate and 80 parts by weight of i-amino-5-benzoylaminoanthraquinone Heated to? Io ° for 24 hours. The melt is worked up as in Example i. A dye is obtained which dyes cotton from the vat black-brown.
3. Verwendet man in Beispiel 2 an Stelle des i -Amino -5 -benzoylaminoanthrachinon 6o Gewichtsteile i-Amino-4-methoxyanthrachinon, so erhält man ein gelbbraun färbendes Produkt.3. Is used in Example 2 instead of the i -amino -5-benzoylaminoanthraquinone 60 parts by weight of i-amino-4-methoxyanthraquinone, a yellow-brown color is obtained Product.
4. Wird der Austausch wie in Beispiel 3 mit i-Aminoanthrachinon-2-aldehyd statt Aminomethoxyanthrachinon vorgenommen, erhält man ein gedecktes Braun.4. If the exchange is as in Example 3 with i-aminoanthraquinone-2-aldehyde made instead of aminomethoxyanthraquinone, a muted brown is obtained.
5. An Stelle des in Beispiel i genannten Dibromderivates des Farbstoffes gemäß Patent 507 340 kann man das Bromierungsprodukt des Farbstoffes gemäß Patent 430 559 in der in den vorstehenden Beispielen ausgeführten Weise mit Aminoanthrachinon, Aminobenzoylaminoanthrachinon, Aminomethoxyanthrachinon, Aminoanthrachinonaldehyd usw. umsetzen und. erhält olivbraune bis rotbraune Küpenfarbstoffe.5. Instead of the dibromo derivative of the dye mentioned in Example i according to patent 507 340 one can use the bromination product of the dye according to patent 430 559 in the manner detailed in the preceding examples with aminoanthraquinone, Aminobenzoylaminoanthraquinone, aminomethoxyanthraquinone, aminoanthraquinone aldehyde etc. implement and. receives olive-brown to red-brown vat dyes.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI37914D DE515331C (en) | 1929-05-02 | 1929-05-02 | Process for the preparation of Kuepen dyes of the anthracene series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI37914D DE515331C (en) | 1929-05-02 | 1929-05-02 | Process for the preparation of Kuepen dyes of the anthracene series |
Publications (1)
Publication Number | Publication Date |
---|---|
DE515331C true DE515331C (en) | 1931-01-03 |
Family
ID=7189646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI37914D Expired DE515331C (en) | 1929-05-02 | 1929-05-02 | Process for the preparation of Kuepen dyes of the anthracene series |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE515331C (en) |
-
1929
- 1929-05-02 DE DEI37914D patent/DE515331C/en not_active Expired
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