CH247611A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH247611A
CH247611A CH247611DA CH247611A CH 247611 A CH247611 A CH 247611A CH 247611D A CH247611D A CH 247611DA CH 247611 A CH247611 A CH 247611A
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 CH247611A publication Critical patent/CH247611A/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

  

      Verfahren        zur        Herstellung        eines        Küpenfarbatoffes.       Es     wurde    gefunden, dass ein wertvoller       Küpenfarbstoff    hergestellt werden kann,  wenn man 1     Mol        1,8-Diaminoanthrachinon-          2,7-dicarbonsäure    oder eines ihrer funktio  nellen Derivate mit 2     Mol        1-Amino-4-benzoyl-          aminoanthrachinon    umsetzt.  



  Der neue Farbstoff ist ein     dunkelrotes     Pulver, das sich in     konz.    Schwefelsäure mit  roter Farbe löst und Baumwolle aus     schwa.rz-          oliver        Küpe    in     blaustichigen    Bordeauxtönen  färbt.  



  Zur Durchführung der Umsetzung kann  die genannte     Dicarbonsäure    oder vorzugs  weise eines ihrer funktionellen Derivate, bei  spielsweise ein     Säurehalogenid    und insbeson  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.          Beispiel:     Zu einer Lösung von 17,1 Teilen     1-Amino-          4-benzoylaminoanthrachinon    in 500 Teilen  trockenem     Nitrobenzol    gibt man bei 90-100   9,1 Teile     1,8-Diaminoanthrachinon-2,7-di-          carbonsäurechlorid.    Hierauf erhöht man die    Temperatur     innert    1/2 Stunde auf 150  und  rührt zur Beendigung der     Farbstoffbildung     noch 2     Stunden    bei 150-160  nach.

   Man fil  triert in der Wärme ab, wäscht mit     Nitro-          benzol    und Alkohol aus und trocknet.



      Process for the production of a vat dye. It has been found that a valuable vat dye can be produced by reacting 1 mole of 1,8-diaminoanthraquinone-2,7-dicarboxylic acid or one of its functional derivatives with 2 moles of 1-amino-4-benzoylaminoanthraquinone.



  The new dye is a dark red powder that is in conc. Sulfuric acid dissolves with a red color and dyes cotton from black and olive vat in blue-tinged Bordeaux tones.



  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, are suitable.

   The reaction can be carried out, for example, at elevated temperature, in the presence or absence of acid-binding agents. Example: 9.1 parts of 1,8-diaminoanthraquinone-2,7-dicarboxylic acid chloride are added at 90-100 to a solution of 17.1 parts of 1-amino-4-benzoylaminoanthraquinone in 500 parts of dry nitrobenzene. The temperature is then increased to 150 within 1/2 hour and the mixture is stirred at 150-160 for a further 2 hours to complete the formation of the dye.

   It is filtered off in the heat, washed with nitrobenzene and alcohol and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man 1 Mol 1,8-Diaminoanthrachinon-2,7-dicarbon- säure oder eines ihrer funktionellen Derivate mit 2 Möl 1-Amino-4-benzoylam.inoanthra- chinon umsetzt. Der neue Farbstoff ist ein dunkelrotes Pulver, das sich in konz. Schwefelsäure mit roter Farbe löst und Baumwolle aus schwarz oliver Küpe in blaustichigen Bordeauxtönen färbt. UNTERANSPRÜCHE: 1. PATENT CLAIM: Process for the production of a vat dye, characterized in that 1 mol of 1,8-diaminoanthraquinone-2,7-dicarboxylic acid or one of its functional derivatives is reacted with 2 mol of 1-amino-4-benzoylaminoanthraquinone . The new dye is a dark red powder that is in conc. Sulfuric acid dissolves red and dyes cotton from a black olive vat in blue-tinged Bordeaux tones. SUBCLAIMS: 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. ä. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Durchführung der Umsetzung in einem hochsiedenden indiffe renten Lösungsmittel. Process according to claim, characterized by the use of an acid halide of dicarboxylic acid. 2. The method according to claim, characterized by the use of the acid chloride of the dicarboxylic acid. Ä. Method according to claim, characterized by carrying out the reaction in a high-boiling indifferent solvent.
CH247611D 1943-06-24 1943-06-24 Process for the production of a vat dye. CH247611A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH243843T 1943-06-24
CH247611T 1943-06-24

Publications (1)

Publication Number Publication Date
CH247611A true CH247611A (en) 1947-03-15

Family

ID=25728845

Family Applications (1)

Application Number Title Priority Date Filing Date
CH247611D CH247611A (en) 1943-06-24 1943-06-24 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH247611A (en)

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