CH293901A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH293901A
CH293901A CH293901DA CH293901A CH 293901 A CH293901 A CH 293901A CH 293901D A CH293901D A CH 293901DA CH 293901 A CH293901 A CH 293901A
Authority
CH
Switzerland
Prior art keywords
sep
production
acid
vat
blue
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 CH293901A publication Critical patent/CH293901A/en

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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

Landscapes

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 252533.    Verfahren zur     Herstellung    eines     Küpenfarbstoffes.       Es wurde gefunden, dass ein wertvoller       Küpenfarbstoff    hergestellt werden kann, wenn  man     1-Amino-4-(p-clilor-benzoyl-amino)-an-          thrachinon    mit einem funktionellen Derivat  der in     4-Stellung    durch eine     N-Methyl-isopro-          pyl-sulfamidgruppe    substituierten     Benzol-l-          carbonsäure    umsetzt.  



  Der neue Farbstoff löst sich in     konz.     Schwefelsäure mit rotbrauner Farbe und färbt  Baumwolle aus blaugrauer     Küpe    in reinen,  blaustichigen Scharlachtönen.  



  Als funktionelles Derivat der genannten       Carbonsäure    kann mit Vorteil ein Säurehalo  genid, beispielsweise das Säurechlorid, ver  wendet werden. Die Umsetzung kann zweck  mässig in einem indifferenten Lösungsmittel,  vorteilhaft bei erhöhter Temperatur, vorge  nommen werden.  



  Die für das vorliegende Verfahren verwen  dete     p-[N-Met.hyl-isopropyl]-sulfamidbenzoe-          säure    kann wie folgt hergestellt werden  53 Teile     Isopropylamin    werden mit 150  Teilen Wasser vermischt und unter gutem Rüh  ren 22 Teile     p-Sulfochloridbenzoesäure    zuge  fügt. Die Temperatur steigt gegen 40 . Nach       zweistündigem        Rühren        wird        mit        10        %        iger     Salzsäure angesäuert,     abgenutscht,    ausgewa  schen und getrocknet.

   Die     p-[N-Isopropyl]-          sulfamidbenzoesäure    bildet farblose Kristalle  vom     Smp.    2l.4 bis 216 .  
EMI0001.0029     
  
    C <SEP> gef. <SEP> = <SEP> 49,29 <SEP> % <SEP> C <SEP> bezech. <SEP> = <SEP> 49,39 <SEP> 0/0
<tb>  H <SEP> gef. <SEP> = <SEP> 5,26 <SEP> % <SEP> H <SEP> bezech. <SEP> = <SEP> 5,35 <SEP> 0/0     
EMI0001.0030     
  
    N <SEP> gef. <SEP> = <SEP> 5,87 <SEP> % <SEP> N <SEP> bezech. <SEP> = <SEP> 5,76 <SEP> %
<tb>  S <SEP> gef. <SEP> = <SEP> <B>13,231/9</B> <SEP> S <SEP> bezech.

   <SEP> = <SEP> 13,1-711/o       Durch     Methylieren    mit     Dimethy        lsnlfat    bei 100  bis 102  in alkalischem     Medium    erhält man die  p - [N     -Metliyl    -     isopropyl    ] -     sul    f     amidbenzoesäure     vom     Smp.    175 .  



  <I>Beispiel:</I>  In 360 Teile Nitrobenzol werden unter  Rühren bei gewöhnlicher     Temperatur    23,l.  Teile     p-[N-Methyl-isopropyl]-sulfamidbenzoe-          säure,    3.5,7 Teile     1-Amino-4-(p-chlor-beiizoyl-          amino)-anthrachinon    und 15 Teile     Thionyl-          chlorid    eingetragen. Nun wird in einer Stunde  auf 87 bis 90  erwärmt und zwölf Stunden  diese Temperatur gehalten. Man lässt hierauf  erkalten,     nutseht    ab und wäscht nacheinander  mit Nitrobenzol, Alkohol und Wasser aus.



  <B> Additional patent </B> to main patent no. 252533. Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1-amino-4- (p-clilor-benzoyl-amino) -anthrachinone with a functional derivative of the 4-position by an N-methyl-isopro- pyl-sulfamidgruppe substituted benzene-1-carboxylic acid.



  The new dye dissolves in conc. Sulfuric acid with a red-brown color and dyes cotton from a blue-gray vat in pure, blue-tinged scarlet tones.



  An acid halide, for example the acid chloride, can advantageously be used as the functional derivative of the carboxylic acid mentioned. The reaction can advantageously be carried out in an inert solvent, advantageously at an elevated temperature.



  The p- [N-methyl-isopropyl] -sulfamidobenzoic acid used for the present process can be prepared as follows. 53 parts of isopropylamine are mixed with 150 parts of water and 22 parts of p-sulfochlorobenzoic acid are added with thorough stirring. The temperature rises around 40. After two hours of stirring, it is acidified with 10% hydrochloric acid, suction filtered, washed out and dried.

   The p- [N-isopropyl] - sulfamidobenzoic acid forms colorless crystals with a melting point of 21.4 to 216.
EMI0001.0029
  
    C <SEP> found. <SEP> = <SEP> 49.29 <SEP>% <SEP> C <SEP> meaning. <SEP> = <SEP> 49.39 <SEP> 0/0
<tb> H <SEP> found. <SEP> = <SEP> 5.26 <SEP>% <SEP> H <SEP> meaning. <SEP> = <SEP> 5.35 <SEP> 0/0
EMI0001.0030
  
    N <SEP> found <SEP> = <SEP> 5.87 <SEP>% <SEP> N <SEP> meaning. <SEP> = <SEP> 5.76 <SEP>%
<tb> S <SEP> found. <SEP> = <SEP> <B> 13,231 / 9 </B> <SEP> S <SEP> denotes.

   <SEP> = <SEP> 13,1-711 / o Methylation with dimethyl sulfate at 100 to 102 in an alkaline medium gives p - [N-methyl-isopropyl] -sulfamide benzoic acid with a melting point of 175.



  <I> Example: </I> In 360 parts of nitrobenzene, while stirring at ordinary temperature, 23.1. Parts of p- [N-methyl-isopropyl] -sulfamidbenzoic acid, 3.5.7 parts of 1-amino-4- (p-chloro-beiizoyl-amino) -anthraquinone and 15 parts of thionyl chloride were added. It is now heated to 87 to 90 in one hour and this temperature is maintained for twelve hours. It is then left to cool, removed and washed out successively with nitrobenzene, alcohol and water.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeiehnet, dass man l -Ainino-4- (p-chlor-benzoyl.-amino) - anthrachi- non mit einem funktionellen Derivat der in 4-Stellung durch eine N-Metliyl-isopropyl-sulf- amidgruppe substituierten Benzol-l-ca.rbon- säure umsetzt. PATENT CLAIM Process for the production of a vat dye, characterized in that l -Ainino-4- (p-chloro-benzoyl.-amino) - anthraquinone with a functional derivative of the 4-position by an N-methyl-isopropyl -sulf- amidgruppe substituted benzene-l-carbonic acid. Der neue Farbstoff löst sich in konz. Schwefelsäure mit rotbrauner Farbe und färbt Baumwolle aus blaugrauer Küpe in reinen, blaustichigen Seharlachtönen. The new dye dissolves in conc. Sulfuric acid with a red-brown color and dyes cotton from a blue-gray vat in pure, blue-tinged seharl-light tones.
CH293901D 1944-08-03 1946-07-11 Process for the production of a vat dye. CH293901A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252533T 1944-08-03
CH293901T 1946-07-11

Publications (1)

Publication Number Publication Date
CH293901A true CH293901A (en) 1953-10-15

Family

ID=25729661

Family Applications (1)

Application Number Title Priority Date Filing Date
CH293901D CH293901A (en) 1944-08-03 1946-07-11 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH293901A (en)

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