DE645897C - Process for the preparation of anthraquinone dyes - Google Patents

Process for the preparation of anthraquinone dyes

Info

Publication number
DE645897C
DE645897C DEI52935D DEI0052935D DE645897C DE 645897 C DE645897 C DE 645897C DE I52935 D DEI52935 D DE I52935D DE I0052935 D DEI0052935 D DE I0052935D DE 645897 C DE645897 C DE 645897C
Authority
DE
Germany
Prior art keywords
preparation
sulfuric acid
anthraquinone dyes
dyes
acid ester
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
Application number
DEI52935D
Other languages
German (de)
Inventor
Dr Hans Raab
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI52935D priority Critical patent/DE645897C/en
Application granted granted Critical
Publication of DE645897C publication Critical patent/DE645897C/en
Expired legal-status Critical Current

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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Anthrachinonfarbstoffen Gegenstand vorliegender Erfindung ist die Herstellung von neuen sauren Wollfarbstoffen der Anthrachinonreihe. Das Verfahren ist dadurch gekennzeichnet, daß man in 4-Bromalizarin-(3-schwefelsäureester das Bromatom gegen Reste aromatischer Amine austauscht und die erhältlichen Produkte gegebenenfalls nachsulfoniert. Die Umsetzung erfolgt zweckmäßig in wäßrigem Medium, gegebenenfalls unter Zusatz von Alkohol. Als säurebindendes Mittel wird zweckmäßig Alkalicarbonat, gegebenenfalls unter Zusatz von Kupfersalzen, angewendet.Process for the preparation of anthraquinone dyes is the subject of the present invention Invention is the production of new acidic wool dyes of the anthraquinone series. The process is characterized in that in 4-bromoalizarine- (3-sulfuric acid ester the bromine atom exchanged for residues of aromatic amines and the available products optionally post-sulfonated. The reaction is expediently carried out in an aqueous medium, optionally with the addition of alcohol. As an acid-binding agent is appropriate Alkali carbonate, optionally with the addition of copper salts, applied.

Die erhaltenen Farbstoffe sind, soweit sie nicht nachsulfoniert wurden, als 4-Arylaminoalizarin-ß-schwefelsäureester aufzufassen. Soweit die Produkte seiner Nachsulfonierung unterworfen wurden, enthalten sie noch eine Sulfogruppe in dem aromatischen Kern, während der esterartig gebundene Schwefelsäurerest abgespalten ist. Alle diese Farbstoffe färben Wolle violett bis blau,und liefern bei der Nachchnomierung blaugrüne, graue bis schwarze Töne von hervorragenden Echtheitseigenschaften.The dyes obtained are, if they have not been post-sulfonated, to be understood as 4-arylaminoalizarin-ß-sulfuric acid ester. So much for his products Subsequent sulfonation were subjected, they still contain a sulfo group in the aromatic nucleus, while the ester-like bonded sulfuric acid residue is split off is. All of these dyes dye wool purple to blue, and deliver when re-chromating blue-green, gray to black shades with excellent fastness properties.

4-Bromalizarin kann aus 4-Aminoalizarin durch Diazotieren und Umsetzen nach S a n d -m e y e r hergestellt werden. Es stellt ein orangegelbes Pulver dar und ist in Natronlauge mit rotvioletter Farbe, in Schwefelsäure mit roter Farbe löslich.4-Bromalizarin can be converted from 4-Aminoalizarin by diazotizing and reacting according to S a n d -m e y e r. It is an orange-yellow powder and is in caustic soda with red-violet color, in sulfuric acid with red color soluble.

Beispiel I 25 g 4 - Bromalizarin-ß-schwefelsäureester 85 % (erhältlich aus 4-Bromalizarin gemäß dem Verfahren des Patents 49I 424) werden in Gegenwart von Soo g Wasser mit 25 g Soda, 20 g p-Anisidin und o,5 g Kupferchlorür 3 Stunden auf 8o° erhitzt. Der gebildete Farbstoff wird mit Kochsalz gefällt, abgesaugt und aus Wasser umgelöst. Auf Wolle nachchnomiert liefert er sehr echte blaugrüne Töne.Example I 25 g of 4-bromalizarin-ß-sulfuric acid ester 85% (available from 4-bromoalizarin according to the method of patent 49I 424) are in the presence Soo g of water with 25 g of soda, 20 g of p-anisidine and 0.5 g of copper chloride for 3 hours heated to 80 °. The dye formed is precipitated with table salt, filtered off with suction and dissolved from water. Changed on wool, it delivers very real blue-green tones.

Beispiel 2 Aus dem 4 - Bromalizarin-ß-schwefelsäureester gemäß Beispiel I wird in analoger Weise mit p-Aminophenol ein grau- bis grünstickiges Schwarz erhalten, welches durch Nachsulfonierung mit Oleumborsäure in ein neutrales Schwarz übergeht.Example 2 From the 4-bromalizarin-ß-sulfuric acid ester according to example I a grayish to greenish black is obtained in an analogous manner with p-aminophenol, which turns into a neutral black through post-sulfonation with oleumboric acid.

Als Beispiele für andere aromatische Amine seien p-Phenylendiamin und 5-Aminosalicylsäure genannt. Dieselben liefern mit dem obergenannten Ausgangsprodukt Anthrachinonfarbstoffe, welche, auf Wolle nachchromiert, sehr echte graue bis schwarze Töne liefern.Examples of other aromatic amines are p-phenylenediamine and called 5-aminosalicylic acid. They deliver with the above-mentioned starting product Anthraquinone dyes, which, after chrome-plated on wool, are very real gray to black Deliver tones.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe, dadurch ege kennzeichnet, daß man in 4-Bromalizarinß-schwefelsäureester das Bromatom gegen Reste aromatischer Amine austauscht und die erhältlichen Produkte gegebenenfalls nachsulfoniert. a :'PATENT CLAIM Process for the production of dyes of the anthraquinone series, characterized ege that in 4-bromoalizarine-sulfuric acid ester the bromine atom exchanged for residues of aromatic amines and the available products if necessary post-sulfonated. a: '
DEI52935D 1935-08-03 1935-08-03 Process for the preparation of anthraquinone dyes Expired DE645897C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI52935D DE645897C (en) 1935-08-03 1935-08-03 Process for the preparation of anthraquinone dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI52935D DE645897C (en) 1935-08-03 1935-08-03 Process for the preparation of anthraquinone dyes

Publications (1)

Publication Number Publication Date
DE645897C true DE645897C (en) 1937-06-04

Family

ID=7193480

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI52935D Expired DE645897C (en) 1935-08-03 1935-08-03 Process for the preparation of anthraquinone dyes

Country Status (1)

Country Link
DE (1) DE645897C (en)

Similar Documents

Publication Publication Date Title
DE645897C (en) Process for the preparation of anthraquinone dyes
DE632083C (en) Process for the production of acidic dyes of the anthraquinone series
DE697000C (en) Process for the preparation of o-oxyazo dyes
AT158864B (en) Process for the preparation of water-soluble dyes for cellulose esters and ethers and processes for dyeing and printing cellulose esters and ethers.
DE409281C (en) Process for the production of acidic monoazo dyes for wool
DE749166C (en) Process for the preparation of monoazo dyes
DE617665C (en) Process for the preparation of monoazo dyes
DE855140C (en) Process for the production of azo dyes
DE501232C (en) Process for the preparation of dyes of the anthraquinone series
DE719304C (en) Process for the preparation of a Kuepen dye
DE540217C (en) Process for the production of azo dyes
DE620837C (en) Process for the production of colored lakes of the anthraquinone series
AT166452B (en) Process for the production of new chromium-containing monoazo dyes
DE632446C (en) Process for the preparation of anthraquinone dyes
CH194949A (en) Process for the preparation of a new monoazo dye.
CH209528A (en) Process for the preparation of an azo dye.
CH302404A (en) Process for the preparation of a trisazo dye.
CH187431A (en) Process for the production of an acidic wool dye of the anthraquinone series.
CH197586A (en) Process for the production of a vat dye of the anthraquinone acridone series.
CH190158A (en) Process for the preparation of a chromable dye of the anthraquinone series.
CH191148A (en) Process for the preparation of a monoazo dye.
CH183592A (en) Process for the preparation of an azo dye.
CH228850A (en) Process for the production of a new anthraquinone dye.
CH218365A (en) Process for the preparation of a 1,1'-dioxyazo dye.
CH189137A (en) Process for the production of an anthraquinone derivative.