CH243843A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH243843A
CH243843A CH243843DA CH243843A CH 243843 A CH243843 A CH 243843A CH 243843D A CH243843D A CH 243843DA CH 243843 A CH243843 A CH 243843A
Authority
CH
Switzerland
Prior art keywords
acid
red
production
dye
vat dye
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 CH243843A publication Critical patent/CH243843A/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

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

Description

  

  Verfahren zur Herstellung eines     Kiipenfarbstoffes.            Es    wurde gefunden, dass ein wertvoller       I'üpenfarbstoff        hergestellt    werden kann,  wenn     man    1     Mol        1,5-Di@aminoanthraehinon-          2,6-dicarbonsäure    oder eines ihrer funktionel  len     Derivate    mit 2     Mol        1-Amino-5-benzoyl-          aminoanthrachinon    umsetzt.  



  Der neue Farbstoff ist ein     rotbraunes    Pul  ver, das sich in konzentrierter Schwefelsäure  mit roter Farbe löst und     Baumwolle    aus       schwarzoliver        güpe    in blaustichig     rotbraunen     Tönen färbt.  



  Zur Durchführung der Umsetzung kann  die genannte     Diearbonsäure    oder     vorzugs-          weise    eines ihrer funktionellen Derivate,     bei-          spiel.sweiee    das Säurechlorid, verwendet wer  den. Die Reaktion wird zweckmässig, in einem  indifferenten     Lösungs-        bezw.    Verteilungsmit  tel vorgenommen, wobei     insbesondere,    solche  von     höherem        Siedepunkt,        wie        Chlorbenzol,     Nitrobenzol oder     Dichlorbenzol,    in Betracht  kommen.

   Man kann die Umsetzung beispiels  weise bei erhöhter Temperatur, in An- oder  Abwesenheit säurebindender Mittel durch  führen.    <I>Beispiel:</I>  Zu der Lösung von 17,1 Teilen     1-Amino-          5-benzoylaminoanthrachinon    in 500 Teilen  trockenem     o-Dichlorbenzol    gibt man bei 80  bis 85  9,1     Teile        1,5-Diaminoanthrachinon-          2;6,dicarbonsäurechlorid.    Nach     zweistündigem     Rühren bei     8f0-8,5     steigert man die     Tempe-          ratur    langsam auf 150 .

   Zur     Beendigung    .der       Farbstoffbildung    rühmt man noch 2     Stunden     bei     150-16ü ,        filtriert    dann in der Wärme  ab, wäscht mit     o-Dichlo@rbenzol    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     tTok-          kenes    Nitrobenzol, 1 Teil     PyTidin        und    17 Teile       Thionylehlorid    hinzu und erhitzt das     Ge-          miseh,    während 1/4     Stunde    auf     90-100'-          Dabei    geht die     1,5-Diaminoanthrachinon-2,6-          dicarbonsäure    in Lösung.

   Man     filtriert    von  einigen     Verunreinigungen    ab und lässt das      Filtrat     erkalten.    Das     1,5-DiaminoanthTachi-          non-2,6-dicarbonsäure,chlorid        kristallisiert    in  grünlich     schillernden,    rotbraunen     Nadeln    aus.

    Es     wird    abgesaugt, mit     Aceton        und        Wasser     (zur Entfernung von     salzsaurem        Pyridin)        ge-          waschen        und    im     Egsiccator    getrocknet.



  Process for the preparation of a Kiipen dye. It has been found that a valuable tepen dye can be produced if 1 mole of 1,5-di @ aminoanthraehinone-2,6-dicarboxylic acid or one of its functional derivatives is reacted with 2 moles of 1-amino-5-benzoyl-aminoanthraquinone .



  The new dye is a red-brown powder that dissolves in concentrated sulfuric acid with a red color and dyes cotton made of black olive güpe in bluish red-brown tones.



  The diacid mentioned or, preferably, one of its functional derivatives, for example the acid chloride, can be used to carry out the reaction. The reaction is expedient in an indifferent solution or. Distribution means made tel, 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. <I> Example: </I> 9.1 parts of 1,5-diaminoanthraquinone-2,6 are added at 80 to 85 to the solution of 17.1 parts of 1-amino-5-benzoylaminoanthraquinone in 500 parts of dry o-dichlorobenzene , dicarboxylic acid chloride. After stirring for two hours at 80-8.5, the temperature is slowly increased to 150.

   To terminate the formation of the dyestuff, the mixture is heated for a further 2 hours at 150-16 °, then filtered off in the warm, washed with o-dichlorobenzene 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 ttokkenes nitrobenzene, 1 part of PyTidine and 17 parts of thionyl chloride are then added to the fine suspension, and the mixture is heated to 90-100% for 1/4 hour. The 1,5-diaminoanthraquinone goes up -2,6- dicarboxylic acid in solution.

   Some impurities are filtered off and the filtrate is allowed to cool. The 1,5-diaminoanth-tachinon-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 an Egsiccator.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines Küpen- farbstoffes,dadurch gekennzeichnet, dass man 1 Mol 1,5-Diaminoanthrachinon-2',6-.dicaTbon- säure oder eines ihrer funktionellen Derivate mit 2 Mol 1-Amino-5-benzoylaminoanthra- chinon umsetzt. PATENT CLAIM Process for the production of a vat dye, characterized in that 1 mole of 1,5-diaminoanthraquinone-2 ', 6-.dicaTbon- acid or one of its functional derivatives is reacted with 2 moles of 1-amino-5-benzoylaminoanthraquinone. Der neue Farbstoff ist ein .rotbraunes Pul ver, das sich in konzentrierter Schwefelsäure mit roter Farbe löst und Baumwolle aus schwarzoliver Küpe in blaustichig rotbraunen Tönen färbt. UNTERANSPRüCHE 1. Verfahren gemäss Patentanspruch, ge kennzeichnet durch die Verwendung des Säurechlorids der Dicarbonsäure. 2. The new dye is a red-brown powder that dissolves in concentrated sulfuric acid with a red color and dyes cotton from a black and olive vat in bluish red-brown tones. SUBClaims 1. Method according to claim, characterized by the use of the acid chloride of the dicarboxylic acid. 2. Verfahren gemäss Patentanspruch, ge- li:ennzeichnel; durch. die Durchführung der Umsetzung in einem hochsiedenden indiffe renten .Lösungsmittel. Method according to claim, li: ennzeichnel; by. the implementation of the reaction in a high-boiling indifferent solvent.
CH243843D 1943-06-24 1943-06-24 Process for the production of a vat dye. CH243843A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH243843A true CH243843A (en) 1946-08-15

Family

ID=4463846

Family Applications (1)

Application Number Title Priority Date Filing Date
CH243843D CH243843A (en) 1943-06-24 1943-06-24 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH243843A (en)

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