CH257943A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH257943A
CH257943A CH257943DA CH257943A CH 257943 A CH257943 A CH 257943A CH 257943D A CH257943D A CH 257943DA CH 257943 A CH257943 A CH 257943A
Authority
CH
Switzerland
Prior art keywords
production
vat dye
acid
dye
benzene
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 CH257943A publication Critical patent/CH257943A/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

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

Description

  

      Verfähren    zur Herstellung eines     Küpenfarbstoffes.       Es wurde     gefunden,    dass ein wertvoller       Küpenfarbstoff        hergestellt    werden kann,  wenn man     1-Amino-5-benzoylaminoanthra-          chinon    mit dem Säurechlorid der in     4-Stel-          lung    durch eine     Sulfodi-(chloräthyl)-amid-          grupp:e        substituierten        Benzol-l-carbonsäure     umsetzt.  



  Der neue Farbstoff     bildet    goldgelbe     Nä-          delcUen,    löst sich in     konz.    Schwefelsäure mit  roter Farbe und färbt Baumwolle aus     rot-          violetter        Küpe    in echten, reinen gelben Tönen.  



  Das für das, vorliegende Verfahren be  nötigte     Säurechlorid    des     Benzol-l-carbon-          säure-4-sulfodi-(chloräthyl)-amids    lässt sich  zum Beispiel     durch        Umsetzen    von     Benzoe-          säure-4-sulfochlorid    mit einer wässerigen     Di-          äthanolanlinlösung    und     Behandlung    des ab  geschiedenen, und getrockneten Produktes mit       Thionylchlorid    herstellen,

   wobei ausser der  Bildung des     Säurechlorids    auch ein Ersatz  der     Hydroxylgruppen    durch Chlor     erfolgt.     Die     Umsetzung    mit dem     Säurechlorid    kann  zweckmässig in einem     indifferenten    Lösungs  mittel vorgenommen werden.  



  <I>Beispiel:</I>  70 Teile fein     pulverisiertes.        Benzol-l-car-          bonsäure    - 4 -     sulfodiäthanolami-d    werden in  2000     Teilen,    wasserfreiem     o-Dichlorbenzol       verteilt und nach Zufügen von 100 Teilen       Thionylchlorid    und einer     geringen    Menge       Pyridin    die Temperatur unter Rühren lang  sam auf 180      gesteigert.    Nachdem die     Tem-          peratur    eine Stunde unter Rühren bei 120  bis 180  belassen wurde,

       destilliert    man das  überschüssige     Thionylchlorid    und etwas     o-          Dichlorbenzol    im Vakuum ab, gibt 82 Teile       1-Amino-5-benzoylaminoanthrachinon    hinzu  und     steigert    die Temperatur unter Rühren  auf 170 bis 175 . Endlich erhitzt man noch  zehn Minuten zum Sieden und lässt erkalten.  Der in guter Ausbeute erhaltene Farbstoff  wird     abfiltriert    und mit heissem Alkohol und  Äther     gewaschen.  



      Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1-amino-5-benzoylaminoanthraquinone is mixed with the acid chloride of the benzene-1 substituted in the 4-position by a sulfodi- (chloroethyl) amide group: e -carboxylic acid converts.



  The new dye forms golden yellow needles, dissolves in conc. Sulfuric acid with red color and dyes cotton from red-violet vats in real, pure yellow tones.



  The acid chloride of benzene-l-carboxylic acid-4-sulfodi- (chloroethyl) -amide required for the present process can be, for example, by reacting benzoic acid-4-sulfochloride with an aqueous diethanolanline solution and treating the Prepare separated and dried product with thionyl chloride,

   In addition to the formation of the acid chloride, the hydroxyl groups are also replaced by chlorine. The reaction with the acid chloride can conveniently be carried out in an inert solvent.



  <I> Example: </I> 70 parts finely powdered. Benzene-1-carboxylic acid - 4 - sulfodiäthanolami-d are distributed in 2000 parts of anhydrous o-dichlorobenzene and, after adding 100 parts of thionyl chloride and a small amount of pyridine, the temperature is slowly increased to 180 with stirring. After the temperature has been left at 120 to 180 for one hour while stirring,

       The excess thionyl chloride and some o-dichlorobenzene are distilled off in vacuo, 82 parts of 1-amino-5-benzoylaminoanthraquinone are added and the temperature is increased to 170 to 175 while stirring. Finally heat it to the boil for another ten minutes and let it cool down. The dye obtained in a good yield is filtered off and washed with hot alcohol and ether.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man 1-Amino-5-benzoylaminoanthrachinon mit dem Säurechlorid der in 4-Stellung durch eine Sulfodi-(chloräthyl)-amidgruppe substi tuierten Benzol-l-carbonsäure umsetzt. Der neue Farbstoff bildet goldgelbe Nä- delchen, löst sich in konz. Schwefelsäure mit roter Farbe und färbt Baumwolle aus rot violetter güpe in echten, reinen gelben Tönen. PATENT CLAIM: A process for the production of a vat dye, characterized in that 1-amino-5-benzoylaminoanthraquinone is reacted with the acid chloride of the benzene-1-carboxylic acid substituted in the 4-position by a sulfodi- (chloroethyl) amide group. The new dye forms golden-yellow needles, dissolves in conc. Sulfuric acid with red color and dyes cotton from red violet güpe in real, pure yellow tones.
CH257943D 1944-08-03 1944-08-03 Process for the production of a vat dye. CH257943A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252533T 1944-08-03
CH257943T 1944-08-03

Publications (1)

Publication Number Publication Date
CH257943A true CH257943A (en) 1948-10-31

Family

ID=25729633

Family Applications (1)

Application Number Title Priority Date Filing Date
CH257943D CH257943A (en) 1944-08-03 1944-08-03 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH257943A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1105082B (en) * 1957-08-31 1961-04-20 Basf Ag Process for the preparation of water-soluble anthraquinone dyes
DE1109290B (en) * 1957-08-31 1961-06-22 Basf Ag Process for the preparation of water-soluble anthraquinone dyes
DE1208436B (en) * 1958-12-31 1966-01-05 Ciba Geigy Process for the production of Kuepen dyes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1105082B (en) * 1957-08-31 1961-04-20 Basf Ag Process for the preparation of water-soluble anthraquinone dyes
DE1109290B (en) * 1957-08-31 1961-06-22 Basf Ag Process for the preparation of water-soluble anthraquinone dyes
DE1208436B (en) * 1958-12-31 1966-01-05 Ciba Geigy Process for the production of Kuepen dyes

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