DE428185C - Process for the preparation of dyes of the dibenzanthrone series - Google Patents

Process for the preparation of dyes of the dibenzanthrone series

Info

Publication number
DE428185C
DE428185C DEB115183D DEB0115183D DE428185C DE 428185 C DE428185 C DE 428185C DE B115183 D DEB115183 D DE B115183D DE B0115183 D DEB0115183 D DE B0115183D DE 428185 C DE428185 C DE 428185C
Authority
DE
Germany
Prior art keywords
dyes
preparation
blue
dibenzanthrone series
parts
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
DEB115183D
Other languages
German (de)
Inventor
Dr Paul Nawiasky
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.)
JG Farbenindustrie AG
Original Assignee
JG 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 JG Farbenindustrie AG filed Critical JG Farbenindustrie AG
Priority to DEB115183D priority Critical patent/DE428185C/en
Application granted granted Critical
Publication of DE428185C publication Critical patent/DE428185C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/22Dibenzanthrones; Isodibenzanthrones
    • C09B3/30Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus
    • C09B3/38Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus by introduction of hydrocarbon or acyl residues into amino groups

Landscapes

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

Description

Verfahren zur Darstellung von Farbstoffen der Dibenzanthronreihe. In der Patentschrift 267418 sind u. a. Kükenfarbstoffe beschrieben, die durch Einführung von Säureresten in Aminoderivate \-on -Dibenzanthronen erhalten werden. Die Farbstoffe, die durch Kochen des Aminoderivates mit dein Säurechlorid erzeugt sind, zeichnen sich, wie daselbst angegeben ist, durch eine vorzügliche Chlorechtheit aus.Process for the preparation of dyes of the dibenzanthrone series. In patent specification 267418, inter alia. Chick dyes described by introduction of acid residues in amino derivatives \ -on -dibenzanthrones are obtained. The dyes, which are produced by boiling the amino derivative with the acid chloride, draw As stated there, they are distinguished by their excellent fastness to chlorine.

Es wurde nun gefunden, daß man ganz rindere Produkte erhält, wenn man acidylierende Mittel in Gegenwart von Verdünnungsinitteln auf Aminorlil>enzanthrone einwirken lüßt. So erhält man z. B. auf diese Weise aus Aminodibenzanthron und Benzoylchlorid einen blauen Farbstoff, während der aus diesen Stoffen nach der Patentschrift 267418 erzeugte Farbstoff violettrot färbt. Die neuen Produkte haben wertvolle färberische Eigenschaften, doch besitzen sie im allgemeinen im Gegensatz zu denen der Patentschrift 267d.18 eine Chlorechtheit, die nicht auf der Höhe derjenigen der besten Küpenfarbstoffe steht. Die Farbstoffe können auch als Ausgangsinaterial zur Herstellung neuer Farbstoffe Verwendung finden.It has now been found that quite bovine products are obtained if acidylating agents in the presence of diluents on aminoril> enzanthrone has an effect. So you get z. B. in this way from aminodibenzanthrone and benzoyl chloride a blue dye, while that of these substances according to patent specification 267418 generated dye turns violet-red. The new products have valuable coloring Properties, but they generally have contrary to those of the patent specification 267d.18 a chlorine fastness which is not on the level of that of the best vat dyes stands. The dyes can also be used as a starting material for the production of new dyes Find use.

Beispiel r.Example r.

5o Teile reines Aininodibenzanthron, das z. B. aus dem gemäß Patent 4o2641 erhältlichen Nitrodibenzanthron hergestellt sein kann, werden in eine Mischung von 5o Teilen Benzoylchlorid und zooo Teilen Nitrobenzol eingetragen. Das Gemisch wird zum Sieden erhitzt und 3 Stunden bei Siedetemperatur gerührt. Beim Erkalten scheidet sich der neue Farbstoff als dunkel gefärbtes Pulver ab, welches sich z. B. in Trichlorbenzol schwer mit blauer Farbe und roter Fluoreszenz löst. Die Lösungsfarbe in konzentrierter Schwefelsäure ist rotstichigviolett. Der neue Farbstoff färbt aus rotstichigblauer Küpe Baumwolle mit der gleichen Farbe an. Bei der Oxydation an der Luft geht die Färbung in ein kräftiges Blau über. Die Färbung wird beim starken Chloren grau.50 parts of pure ainodibenzanthrone, which z. B. from the patent 4o2641 available nitrodibenzanthrone can be made into a mixture of 50 parts of benzoyl chloride and zooo parts of nitrobenzene entered. The mixture is heated to boiling and stirred for 3 hours at boiling temperature. When cooling down the new dye separates as a dark colored powder, which z. B. in trichlorobenzene difficult to solve with blue color and red fluorescence. The solution color in concentrated sulfuric acid is reddish purple. The new dye stains from reddish blue vat cotton of the same color. In the case of oxidation the color changes to a strong blue in the air. The coloring will be when strong Chlorine gray.

Verwendet man an Stelle des Benzovlchlorids o-Ch:lorbenzoylchlorid, so erhält inan einen ähnlichen Farbstoff von etwas rotstickigerer Nuance.If one uses instead of the benzoyl chloride o-Ch: lorbenzoylchlorid, in this way a similar dye with a slightly redder shade is obtained.

Aininoisodibenzanthron geht bei der gleichen Behandlung in ein schönes Violett über. Beispiele.Aininoisodibenzanthrone goes into a nice one with the same treatment Purple over. Examples.

ioo Teile reines Aminodibenzanthron werden mit 2ooo Teilen Nitrobenzol und ioo Teilen Toluolsulfochlorid 3 Stunden bei 16o°gerührt. Aus dein Reaktionsgemisch wird der neue Farbstoff z. B. durch Wasserdampfdestillation abgeschieden. Er bildet ein dunkles Pulver, welches sich in konzentrierter Schwefelsäure rotstichigv iolett, in warmem Trichlorbenzol schwer mit blauer Farbe und roter Fluoreszenz löst. Er färbt aus rotstichigblauer Küpe Baumwolle blaugrün an. Beim Chloren wird die Färbung blaugrau.100 parts of pure aminodibenzanthrone are mixed with 2,000 parts of nitrobenzene and 100 parts of toluenesulfonyl chloride for 3 hours at 160 °. From your reaction mixture the new dye z. B. by steam distillation deposited. It forms a dark powder which turns reddish in concentrated sulfuric acid iolet, difficult to dissolve in warm trichlorobenzene with a blue color and red fluorescence. He dyes cotton blue-green from a reddish-tinged blue vat. With chlorination, the Coloring blue-gray.

Claims (1)

PATrN T-ANSPRUCTf Verfahren zur Darstellung von Farbstoffen der Dibenzanthronreihe, dadurch gekennzeichnet, dafi man Aminoder ivate von Dibenzanthronen in Gegenwart von Verdünnungsmitteln mit acidylierenden Mitteln behandelt.PATrN T-ANSPRUCTf Process for the representation of dyes of the dibenzanthrone series, characterized in that amine derivatives of dibenzanthrones are present in the presence treated by diluents with acidylating agents.
DEB115183D 1924-08-12 1924-08-12 Process for the preparation of dyes of the dibenzanthrone series Expired DE428185C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB115183D DE428185C (en) 1924-08-12 1924-08-12 Process for the preparation of dyes of the dibenzanthrone series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB115183D DE428185C (en) 1924-08-12 1924-08-12 Process for the preparation of dyes of the dibenzanthrone series

Publications (1)

Publication Number Publication Date
DE428185C true DE428185C (en) 1926-04-28

Family

ID=6993956

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB115183D Expired DE428185C (en) 1924-08-12 1924-08-12 Process for the preparation of dyes of the dibenzanthrone series

Country Status (1)

Country Link
DE (1) DE428185C (en)

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