CH257944A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH257944A
CH257944A CH257944DA CH257944A CH 257944 A CH257944 A CH 257944A CH 257944D A CH257944D A CH 257944DA CH 257944 A CH257944 A CH 257944A
Authority
CH
Switzerland
Prior art keywords
production
vat
vat dye
dye
red
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 CH257944A publication Critical patent/CH257944A/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)
  • Coloring (AREA)

Description

  

      Zusatzpatent    zum     Hauptpatent   <B>252533.</B>    Verfahren zur Herstellung eines     Küpenfarbstoffes.       Es wurde gefunden, dass ein wertvoller       Küpenfarbstoff    hergestellt werden kann,  wenn man     1-Amino-4-benzoylaminoanthra-          chinon    mit dem     Säurechlorid    der in     4-Stel-          lung    durch eine     Sulfodi-(chloräthyl)-amid-          gruppe    substituierten     Benzol-l-carbonsäure          umsetzt.     



  Der neue Farbstoff     kristallisiert    in roten       Nädelchen,    löst sich in     konz.    Schwefelsäure  mit roter Farbe und färbt     Baumwolle    aus  braunvioletter     Küpe    in blaustichig roten  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-          äthanolaminlösung    und Behandlung des ab  geschiedenen und     getrockneten    Produktes  mit     Thionylchlorid        herstellen,

      wobei ausser  der Bildung des     Säurechlorids    auch ein Ei  satz der     Hydroxylgruppen    durch Chlor er  folgt. Die Umsetzung mit dem Säurechlorid  kann zweckmässig in einem indifferenten       Lösungsmittel        vorgenommen    werden.

      <I>Beispiel:</I>  70 Teile fein pulverisiertes     Benzol-l-car-          bonsäure-4-sulfodiäthanolamid    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 130  belassen wurde,     destilliert    man das  überschüssige     Thionylchlorid    und etwas     o-Di-          chlorbenzol    im     Vakuum    ab, gibt 82     Teile          1-Amino-4-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       Ather    gewaschen.



      Additional patent to main patent <B> 252533. </B> Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1-amino-4-benzoylaminoanthraquinone is mixed with the acid chloride of the benzene-1-carboxylic acid substituted in the 4-position by a sulfodi- (chloroethyl) amide group implements.



  The new dye crystallizes in red needles and dissolves in conc. Sulfuric acid with red color and dyes cotton from a brownish-violet vat in blue-tinged red tones.



  The acid chloride of benzene-l-carboxylic acid-4-sulfodi- (chloroethyl) -amide required for the present process can be obtained, for example, by reacting benzoic acid-4-sulfochloride with an aqueous diethanolamine solution and treating it 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 of finely powdered benzene-l-carboxylic acid-4-sulfodiethanolamide are distributed in 2000 parts of anhydrous o-dichlorobenzene and, after adding 100 parts of thionyl chloride and a small amount:

      Amount of pyridine, the temperature slowly increased to 180 while stirring. After the temperature has been left at 120 to 130 for one hour with stirring, the excess thionyl chloride and some o-dichlorobenzene are distilled off in vacuo, 82 parts of 1-amino-4-benzoylaminoanthraquinone are added and the temperature is increased to 170 while stirring up to 175.

   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-4-benzoylaminoanthrachinon mit dem Säurechlorid der in 4-Stellung durch eine Sulfodi-(chloräthyl)-amidgruppe substi tuierten Benzol-l-carbonsäure umsetzt. Der neue Farbstoff kristallisiert in roten Nädelchen, Claim: Process for the production of a vat dye, characterized in that 1-amino-4-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 crystallizes in red needles, löst sich in konz.. Schwefelsäure mit roter Farbe und färbt Baumwolle aus braunvioletter Küpe in blaustichig roten Tönen. Dissolves in conc. sulfuric acid with a red color and dyes cotton from a brown-violet vat in blue-tinged red tones.
CH257944D 1944-08-03 1944-08-03 Process for the production of a vat dye. CH257944A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252533T 1944-08-03
CH257944T 1944-08-03

Publications (1)

Publication Number Publication Date
CH257944A true CH257944A (en) 1948-10-31

Family

ID=25729634

Family Applications (1)

Application Number Title Priority Date Filing Date
CH257944D CH257944A (en) 1944-08-03 1944-08-03 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH257944A (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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