CH247604A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH247604A
CH247604A CH247604DA CH247604A CH 247604 A CH247604 A CH 247604A CH 247604D A CH247604D A CH 247604DA CH 247604 A CH247604 A CH 247604A
Authority
CH
Switzerland
Prior art keywords
dicarboxylic acid
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 CH247604A publication Critical patent/CH247604A/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

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr.     243843.       Es wurde     gefunden,        dass:    ein wertvoller       Küpenfarbstoff    hergestellt werden kann,  wenn man 1 Mal     1,5-Diaminoanthrachinon-          2,6-dicarbonsäure    oder eines ihrer funktionel  len     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 schwarz  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 beispiels  weise bei     erhöhter    Temperatur, in An- oder  Abwesenheit säurebindender Mittel durch  führen.

    



  <I>Beispiel:</I>  Zu der     Lösung    von<B>17,1</B> Teilen     1-Amino-          4-benzoylaminoanthrachinon    in 500 Teilen  trockenem Nitrobenzol gibt man bei 90-100   9,1     Teile    1,5 -     Diaminoanthrachinon    = 2,6 -     di-          carbonsäurechlorid.    Hierauf steigert man die  Temperatur     innert        i/.,    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  trockenes Nitrobenzol, 1 Teil     Pyridin    und  17 Teile     Thionylchlorid    hinzu und erhitzt  das Gemisch während     i/4        Stunde    auf 90 bis  100 . Dabei geht die     1,5-Diaminoanthrachi-          non-2,6-dicarbonsäure    in Lösung.

   Man fil  triert von einigen Verunreinigungen ab und  lässt das Filtrat erkalten. Das     1,5-Diamino-          anthrachinon-2,6-dicarbonsäurechlorid    kristal  lisiert in grünlich schillernden, rotbraunen  Nadeln aus. Es wird abgesaugt, mit Aceton  und Wasser (zur Entfernung von salzsaurem       Pyridin)    gewaschen und im     Exsiccator    ge  trocknet.



  <B> Additional patent </B> to main patent No. 243843. It was found that: a valuable vat dye can be produced if 1,5-diaminoanthraquinone-2,6-dicarboxylic acid or one of its functional derivatives is mixed with 2 Mol 1-amino-4-benzoylaminoanthraquinone converts.



  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.



  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> To the solution of <B> 17.1 </B> parts of 1-amino-4-benzoylaminoanthraquinone in 500 parts of dry nitrobenzene, 9.1 parts of 1.5 - Diaminoanthraquinone = 2,6 - dicarboxylic acid chloride. The temperature is then increased to 150 within one 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 chloride used in this example 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 of dry nitrobenzene, 1 part of pyridine and 17 parts of thionyl chloride are then added to the fine suspension, and the mixture is heated to 90 to 100 for 1/4 hour. The 1,5-diaminoanthraquinone-2,6-dicarboxylic acid goes into solution.

   Some impurities are filtered off and the filtrate is allowed to cool. The 1,5-diamino-anthraquinone-2,6-dicarboxylic acid chloride crystallizes out in greenish shimmering, red-brown needles. It is filtered off with suction, washed with acetone and water (to remove hydrochloric acid pyridine) and dried in a desiccator.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man 1 Mol 1,5-Diaminoanthrachinon-2,6-dicarbon- säure oder eines ihrer funktionellen Derivate mit 2 Mol 1-Amino-4-benzoylaminoanthra- ehinon umsetzt. Claim: Process for the production of a vat dye, characterized in that 1 mol of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid or one of its functional derivatives is reacted with 2 mol of 1-amino-4-benzoylaminoanthraquinone. 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. 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. 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. Method 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. 3. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Durchführung der Umsetzung in einem hochsiedenden indiffe renten Lösungmittel. Process according to claim, characterized by the implementation of the reaction in a high-boiling, indifferent solvent.
CH247604D 1943-06-24 1943-06-24 Process for the production of a vat dye. CH247604A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH247604T 1943-06-24
CH243843T 1943-06-24

Publications (1)

Publication Number Publication Date
CH247604A true CH247604A (en) 1947-03-15

Family

ID=25728838

Family Applications (1)

Application Number Title Priority Date Filing Date
CH247604D CH247604A (en) 1943-06-24 1943-06-24 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH247604A (en)

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