CH293902A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH293902A
CH293902A CH293902DA CH293902A CH 293902 A CH293902 A CH 293902A CH 293902D A CH293902D A CH 293902DA CH 293902 A CH293902 A CH 293902A
Authority
CH
Switzerland
Prior art keywords
production
acid
amino
vat dye
parts
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 CH293902A publication Critical patent/CH293902A/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

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

Description

  

      Zitsatzp  ttcaiit    zum Hauptpatent     Nr.252533.       Verfahren     zur    Herstellung eines     Küpenfarbstoffes.       Es wurde     gefunden,    dass ein     wertvoller          Küpenfarbstoff    hergestellt werden kann, wenn  man     1-Amino-l-(p-ehlor-ben7oyl-amino)-an-          thraehinon    mit einem funktionellen Derivat  der in     4-Stellung    durch eine     N-@Iethyl-eyclo-          hexyl-sulfamidgruppe    substituierten     Benzol-l-          carbonsäure    umsetzt.  



  Der neue Farbstoff löst sieh in     konz.     Schwefelsäure mit rotbrauner Farbe und  färbt Baumwolle aus blauer     Kiipe    in reinen       Seharlaehtönen.     



  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 ver  wendete     p-[N-3lethyl-eyelohexyl]-sulfamid-          benzoesäure    kann wie folgt hergestellt werden:       420    Teile     Cyelohexylamin    werden mit 2000  Teilen Wasser vermischt und 220 Teile       p-Sulfo-ehloridbenzoesäiire        zugefügt.    Nach  zweistündigem Rühren bei erhöhter Tempera  tur hat sieh die     p-[Cvelohexyl]-sulfamidben-          zoesäure    gebildet.

   Sie wird in üblicher     Weise     mit     Dimethylsulfat    zur p-[N-Methyl-eyelo-         hexyl]    -     sulfamidbenzoesäure        naehmethyliert     und bildet. nach dem     Umkristallisieren    aus       t11kohol    farblose Nadeln vom     Smp.        212    bis  ?13 .  



       Beispiel:     In     1-1-1:    Teile Nitrobenzol werden bei gewöhn  licher Temperatur 8,9 Teile     p-[N-14lethyl-cyclo-          hexyl]-sulfamidbenzoesäure,   <B>11,9</B> Teile     1-          Amino    - 4-     (p-ehlor        -benzoy    1-     amino)        -anthrachi-          non    und 5 Teile     Thionylehlorid    eingerührt.       Nun    wird in einer Stunde auf 87 bis 90  er  wärmt und 12 Stunden bei dieser Temperatur  gehalten.

   Nach dem Erkalten wird     abge-          nutseht,    nacheinander mit Nitrobenzol, Alko  hol     und    Wasser ausgewaschen und getrocknet.



      Zitsatzp ttcaiit to the 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-1- (p-ehlorben7oyl-amino) -anthraehinone with a functional derivative of the 4-position by an N- @ ethyl-eyclo - Hexyl sulfamide group substituted benzene-1-carboxylic acid reacts.



  The new dye dissolves in conc. Sulfuric acid with a red-brown color and dyes cotton from blue kiipe in pure visual 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 expediently be carried out in an inert solvent, advantageously at an elevated temperature.



  The p- [N-3-ethyl-eyelohexyl] -sulfamidbenzoic acid used for the present process can be prepared as follows: 420 parts of cyelohexylamine are mixed with 2000 parts of water and 220 parts of p-sulfo-chloride benzoic acid are added. After stirring for two hours at an elevated temperature, the p- [Cvelohexyl] -sulfamidbenzoic acid has formed.

   It is methylated in the usual way with dimethyl sulfate to form p- [N-methyl-eyelohexyl] sulfamidobenzoic acid and forms. after recrystallization from alcohol, colorless needles with a melting point of 212 to? 13.



       Example: In 1-1-1: parts of nitrobenzene are converted into 8.9 parts of p- [N-14lethylcyclohexyl] sulfamidobenzoic acid, 11.9 parts of 1- amino-4 at the usual temperature - (p-ehlor -benzoy 1- amino) -anthraquinone and 5 parts of thionyl chloride are stirred in. Now it is heated to 87 to 90 in one hour and held at this temperature for 12 hours.

   After cooling, it is removed, washed out successively with nitrobenzene, alcohol and water and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man 1-Amino-4- (p-chlor-benzoy 1-amino) -anthrachi- non mit einem funktionellen Derivat der in .1-Stellung durch eine N--.#Iethyl-ey clohexyl- sulfa.midgruppe substituierten Benzol-l-ear- bonsäure umsetzt. PATENT CLAIM: Process for the production of a vat dye, characterized in that 1-amino-4- (p-chloro-benzoy 1-amino) -anthraquinone with a functional derivative of the .1-position by an N-- . # Ethyl-ey clohexyl-sulfa.midgruppe substituted benzene-l-earboxylic acid. Der neue Farbstoff löst sieh in konz. Schwefelsäure mit rotbrauner Farbe und färbt Baumwolle aus blauer Küpe in reinen Schar lachtönen. The new dye dissolves in conc. Sulfuric acid with a reddish-brown color and dyes cotton from a blue vat in pure flocks of laughing tones.
CH293902D 1944-08-03 1946-07-11 Process for the production of a vat dye. CH293902A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252533T 1944-08-03
CH293902T 1946-07-11

Publications (1)

Publication Number Publication Date
CH293902A true CH293902A (en) 1953-10-15

Family

ID=25729662

Family Applications (1)

Application Number Title Priority Date Filing Date
CH293902D CH293902A (en) 1944-08-03 1946-07-11 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH293902A (en)

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