CH247605A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH247605A
CH247605A CH247605DA CH247605A CH 247605 A CH247605 A CH 247605A CH 247605D A CH247605D A CH 247605DA CH 247605 A CH247605 A CH 247605A
Authority
CH
Switzerland
Prior art keywords
acid
dicarboxylic acid
production
dye
vat
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH247605A publication Critical patent/CH247605A/en

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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
    • 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
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
    • C09B1/43—Dicarboxylic acids
    • 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
    • C09B5/32—1.3 azoles of the anthracene series

Landscapes

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

Description

  

      Zusatzpatent    zum     Hauptpatent    Nr. 243843.    Verfahren zur Herstellung     eines        Küpenfarbstoffes.       Es wurde gefunden, dass ein wertvoller       Küpenfarbstoff        hergestellt    werden kann,  wenn man 1     Mol        1,5-Diaminoanthraehinon-          2,6-dicarbonsäure    oder eines ihrer funktionel  len Derivate mit 2     Mol        1-Amino-4-methoxy-          anthrachinon    umsetzt.  



  Der neue Farbstoff ist ein dunkelrotes  Pulver; das sich in     konz.    Schwefelsäure mit  gelbroter Farbe löst und Baumwolle aus       schwarzoliver        Küpe    in Bordeauxtönen färbt.  



  Zur Durchführung der Umsetzung kann  die genannte     Dicarbonsäure    oder vorzugs  weise eines ihrer funktionellen     Derivate,    bei  spielsweise ein     Säurehalogenid,    und     insbeson-          i        dere    das Säurechlorid verwendet werden.

   Die  Reaktion wird zweckmässig in einem indiffe  renten     Lösungs-        bezw.        Verteilungsmittel    vor  genommen,     wobei    insbesondere solche von  höherem Siedepunkt, wie Chlorbenzol,     Nitro-          benzol    oder     Dichlorbenzol    in Betracht kom  men. Man kann die Umsetzung beispielsweise  bei erhöhter Temperatur, in An- oder Ab  wesenheit säurebindender     Mittel    durchführen.

      <I>Beispiel:</I>    Zu der Lösung von 12,65 Teilen     1-Amino-          4-methoxyanthrachinon    in 500 Teilen     trok-          kenem    Nitrobenzol gibt man bei 90-100   9,1 Teile     1,5-Diaminoanthrachinon-2,6-dicar-          bonsäurechlorid.    Hierauf     steigert    man die  Temperatur innert     1/2    Stunde auf 150 . Zur  Beendigung der     Farbstoffbildung    rührt man  noch 2 Stunden bei 150-160 , filtriert dann    in der Wärme ab, wäscht mit Nitrobenzol  und Alkohol aus     und    trocknet.  



  Das in diesem Beispiel verwendete Säure- ;  Chlorid kann wie folgt erhalten werden:  5 Teile     1,5-Diaminoanthrachinon-2,6-di-          carbonsäure    werden mit 60 Teilen trockenem  Nitrobenzol vermahlen. Zu der feinen Sus  pension gibt man nun weitere 540 Teile     trok-    .       kenes    Nitrobenzol, 1 Teil     Pyridin    und 17  Teile     Thionylchlorid    hinzu und erhitzt das  Gemisch während     1/.1    Stunde auf 90-100 .  Dabei geht die     1,5-Diaminoanthrachinon-2,6-          diearbonsKure    in Lösung. Man filtriert von  einigen Verunreinigungen ab und lässt das  Filtrat erkalten.

   Das     1,5-Diaminoanthrachi-          non-2,6-dicarbonsäurechlorid    kristallisiert in  grünlich schillernden, rotbraunen Nadeln aus.  Es wird abgesaugt, mit Aceton und Wasser  (zur Entfernung von salzsaurem     Pyridin)        ge-          w:@,@nhPn        nnrl    im     Exsiecator        getrocknet.  



      Additional patent to the main patent No. 243843. Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1 mole of 1,5-diaminoanthraehinone-2,6-dicarboxylic acid or one of its functional derivatives is reacted with 2 moles of 1-amino-4-methoxy-anthraquinone.



  The new dye is a dark red powder; that is in conc. Sulfuric acid dissolves with a yellow-red color and dyes cotton from a black and olive vat in shades of Bordeaux.



  The dicarboxylic acid mentioned or, preferably, one of its functional derivatives, for example an acid halide, and in particular the acid chloride, can be used to carry out the reaction.

   The reaction is expediently in an indifferent solution or. Distribution agents taken before, in particular those with a higher boiling point such as chlorobenzene, nitrobenzene or dichlorobenzene come into consideration. The reaction can be carried out, for example, at elevated temperature, in the presence or absence of acid-binding agents.

      <I> Example: </I> 9.1 parts of 1,5-diaminoanthraquinone-2,6 are added at 90-100 to the solution of 12.65 parts of 1-amino-4-methoxyanthraquinone in 500 parts of dry nitrobenzene -dicarboxylic acid chloride. The temperature is then increased to 150 within 1/2 hour. To complete the formation of the dye, the mixture is stirred for a further 2 hours at 150-160, then filtered off in the heat, washed with nitrobenzene and alcohol and dried.



  The acid used in this example; Chloride can be obtained as follows: 5 parts of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid are ground with 60 parts of dry nitrobenzene. A further 540 parts are now added to the fine suspension. Add kenes nitrobenzene, 1 part pyridine and 17 parts thionyl chloride and heat the mixture to 90-100 for 1/1 hour. The 1,5-diaminoanthraquinone-2,6-diacid goes into solution. Some impurities are filtered off and the filtrate is allowed to cool.

   The 1,5-diaminoanthraquinone-2,6-dicarboxylic acid chloride crystallizes out in greenish shimmering, red-brown needles. It is filtered off with suction, dried with acetone and water (to remove hydrochloric acid pyridine) in a desiecator w: @, @ nhPn.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man 1 112o1 1,5-Diaminoanthrachinon-2,6-dicarbon- säure oder eines ihrer funktionellen Derivate mit 2 Mol 1-Amino-4-methoxyanthrachinon umsetzt. Der neue Farbstoff ist ein dunkelrotes Pulver, das sich in konz. Schwefelsäure mit gelbroter Farbe löst und Baumwolle aus schwarzoliver Küpe in Bordeauxtönen färbt. PATENT CLAIM: Process for the production of a vat dye, characterized in that 1 112o1 1,5-diaminoanthraquinone-2,6-dicarboxylic acid or one of its functional derivatives is reacted with 2 mol of 1-amino-4-methoxyanthraquinone. The new dye is a dark red powder that is in conc. Sulfuric acid dissolves with a yellow-red color and dyes cotton from a black and olive vat in shades of Bordeaux. UNTERAN SPRüCHE 1. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Verwendung eines Säurehalogenids der Dicarbonsäure. 2. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Verwendung des Säurechlorids der Dicarbonsäure. 3. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Durchführung der Umsetzung in einem hochsiedenden indiffe renten Lösungsmittel. SUBJECT DISCLAIMERS 1. Method according to claim, characterized by the use of an acid halide of the dicarboxylic acid. 2. The method according to claim, characterized by the use of the acid chloride of the dicarboxylic acid. 3. The method according to claim, characterized by carrying out the reaction in a high-boiling indifferent solvent.
CH247605D 1943-06-24 1943-06-24 Process for the production of a vat dye. CH247605A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH247605T 1943-06-24
CH243843T 1943-06-24

Publications (1)

Publication Number Publication Date
CH247605A true CH247605A (en) 1947-03-15

Family

ID=25728839

Family Applications (1)

Application Number Title Priority Date Filing Date
CH247605D CH247605A (en) 1943-06-24 1943-06-24 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH247605A (en)

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