CH216597A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

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Publication number
CH216597A
CH216597A CH216597DA CH216597A CH 216597 A CH216597 A CH 216597A CH 216597D A CH216597D A CH 216597DA CH 216597 A CH216597 A CH 216597A
Authority
CH
Switzerland
Prior art keywords
production
sulfuric acid
concentrated sulfuric
vat
dye
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH216597A publication Critical patent/CH216597A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24Dyes 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
    • C09B5/26Carbazoles 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

  

  <B>Zusatzpatent</B> zum     Hauptpatent    Nr. 214180.    Verfahren zur Herstellung eines     Küpenfarbstoffes.       Es wurde gefunden, dass ein     wertvoller          Küpen:forbstoff    hergestellt werden kann,  wenn man     Di-(4'-benzoylamino-1'-anthrachi-          nonyl-)aminothianthren,    worin die     Anthra-          chinonylaminoreste    dieselbe Stellung von       Thianthren    innehaben, wie die     Bromatome     im     Dibromthianthren,

          das    durch     Bromieren     von     Thianthren    erhalten wird, mit konden  sierenden Mitteln behandelt.  



  Der Farbstoff     bildet    ein schwarzviolettes       Pulver,    das sich mit grüner Farbe in konzen  trierter Schwefelsäure löst und Baumwolle  aus rotbrauner     Küpe    in violetten Tönen färbt.  



  Das dem vorliegenden Verfahren     als    Aus  gangsprodukt dienende     Di-(4'-benzoylamino-          1.'-anthraeliinonyl-)aminothianthren    kann wie  folgt hergestellt werden:  3,7     Teile        Dibromthianthren,    7,5 Teile       1-Armino-4-benzoylaminoanthra,chinon,    3     Teile          entwässertes    Soda, 3 Teile     entwässertes          Natriumacetat    und 0,5 Teile     Kupferchlorür     werden 'in 1.00 Teilen Nitrobenzol verteilt  und während 7 Stunden zum Sieden erhitzt.

      Das     I#ealctionsgemiseh    wird nach .dem Er  kalten filtriert, der     Rück        stand    mit Nitro  benzol, Sowie mit     Benzol        und4    Alkohol       gewayschen    und zur     Reinigung    zuerst mit  verdünnter Salzsäure, dann mit Alkohol  ausgekocht. Das in     guter        Ausbeute        erhaltene     Kondensationsprodukt     bildet    ein dunkel  blaues, kristallines Pulver, .das sieh in kon  zentrierter Schwefelsäure mit grüner Farbe  auflöst und nur schwer     verküpt.     



  Als kondensierende Mittel kommen ins  besondere diejenigen in Betracht, die zur Her  stellung von Ringschlüssen, wie     Carbazol-          ringschlüssen,    geeignet sind, wie     Aluminium-          chlorid,    gegebenenfalls zusammen mit     Alkali-          kalogeniden,        Benzylcyanden    und Säurechlo  riden, hauptsächlich     faber        konzentrierte          Schwefelsäure    sowie     ihre        Abkömmlinge,    wie       Chlors.ulfonsäure.     



       Beispiel:     1 Teil des     Umsetzungsproduktes        aus     1     Mol        Dibromthianthren    und 2     Mol        1-Amino-          4-benzoylaminoanthrachinon    wird in 20 Teile           95'3'o        ige        Schwefelsäure    eingetragen und  24 Stunden lang bei<B>18-22</B>   gerührt. Man  giesst auf Eis, fügt 0,3 Teile     Natriumnitrit     hinzu und rührt 16 Stunden bei 18-22  .

    Dann wird filtriert, der     Rückstand    mit Was  ser neutral     gewaschen    und getrocknet.



  <B> Additional patent </B> to main patent no. 214180. Process for the production of a vat dye. It has been found that a valuable vat can be produced if one uses di- (4'-benzoylamino-1'-anthraquinonyl) aminothianthrene, in which the anthraquinonylamino radicals have the same position of thianthrene as the bromine atoms in dibromothianthrene ,

          which is obtained by brominating thianthrene treated with condensing agents.



  The dye forms a black-violet powder that dissolves in concentrated sulfuric acid with a green color and dyes cotton from a red-brown vat in violet tones.



  The di- (4'-benzoylamino- 1 .'-anthraeliinonyl-) aminothianthrene, which is used as the starting product for the present process, can be prepared as follows: 3.7 parts of dibromothianthrene, 7.5 parts of 1-armino-4-benzoylaminoanthra, quinone, 3 parts of dehydrated soda, 3 parts of dehydrated sodium acetate and 0.5 part of copper chloride are distributed in 1.00 parts of nitrobenzene and heated to the boil for 7 hours.

      The reaction mixture is filtered after it is cold, the residue is washed with nitrobenzene, benzene and alcohol and, for cleaning, first boiled with dilute hydrochloric acid and then with alcohol. The condensation product obtained in good yield forms a dark blue, crystalline powder, which dissolves in concentrated sulfuric acid with a green color and only with difficulty evaporates.



  Particularly suitable condensing agents are those which are suitable for the production of ring closures, such as carbazole ring closures, such as aluminum chloride, optionally together with alkali metal halides, benzylcyandic acid and acid chlorides, mainly concentrated sulfuric acid and its derivatives, like chlorosulfonic acid.



       Example: 1 part of the reaction product of 1 mole of dibromothianthrene and 2 moles of 1-amino-4-benzoylaminoanthraquinone is introduced into 20 parts of 95% strength sulfuric acid and stirred for 24 hours at 18-22. It is poured onto ice, 0.3 part of sodium nitrite is added and the mixture is stirred at 18-22 for 16 hours.

    It is then filtered, the residue washed neutral with water and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man Di - W- benzoy lamino -<B>l'-</B> anthrachinonyl - ) aminothianthren, worin die Anthrachinonyl- aminorestedieselbe Stellung von Thianthren innehaben, wie die Bromatome im Dibrom- thianthren, Claim: A process for the production of a vat dye, characterized in that di - W - benzoy lamino - <B> l'- </B> anthraquinonyl -) aminothianthrene, in which the anthraquinonyl amino group has the same position of thianthrene as the bromine atoms in dibromothianthrene, das durch Bromieren von Thian- thren erhalten wird, mit kondensierenden Mitteln behandelt. Der Farbstoff bildet ein schwarzviolettes Pulver, das sich mit grüner Farbe in konzen trierter Schwefelsäure löst und Baumwolle aus rotbrauner Küpe in violetten Tönen färbt. UNTERANSPRUCH: Verfahren nach Patentansrpueh, gekenn zeichnet durch die Verwendung von konzen trierter Schwefelsäure als kondensierendes Mittel. which is obtained by bromination of thiantrene treated with condensing agents. The dye forms a black-violet powder that dissolves in concentrated sulfuric acid with a green color and dyes cotton from a red-brown vat in violet tones. SUBClaim: Process according to patent claim, characterized by the use of concentrated sulfuric acid as a condensing agent.
CH216597D 1939-04-15 1939-04-15 Process for the production of a vat dye. CH216597A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH216597T 1939-04-15
CH214180T 1939-04-15

Publications (1)

Publication Number Publication Date
CH216597A true CH216597A (en) 1941-08-31

Family

ID=25725562

Family Applications (1)

Application Number Title Priority Date Filing Date
CH216597D CH216597A (en) 1939-04-15 1939-04-15 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH216597A (en)

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