CH216596A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

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Publication number
CH216596A
CH216596A CH216596DA CH216596A CH 216596 A CH216596 A CH 216596A CH 216596D A CH216596D A CH 216596DA CH 216596 A CH216596 A CH 216596A
Authority
CH
Switzerland
Prior art keywords
production
sulfuric acid
dye
concentrated sulfuric
parts
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 CH216596A publication Critical patent/CH216596A/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

  

  Zusatzpatent zum     Hauptpatent    Nr. 214180.    Verfahren zur Herstellung eines     Nüpenfarbstof%s.       Es wurde gefunden, dass ein wertvoller       liüpenfarbstoff        hergestellt    werden kann,  wenn man     Di-(4'-benzoyla@mino-1'-.anthrachi-          nony        1-)aminodinaphthylenthiophen,    das durch       Dibromieren    von     Dinaphthylenthiophen    und  Ersatz     dc-r    Bromatome durch     1-Amino-4-          benzoylaminoanthra,chinonreste    erhältlich ist,

    mit     kondensierenden    Mitteln     behandelt.     



  Der Farbstoff     bildet    ein schwarzes Pul  ver,     das    sich mit     violetter    Farbe in konzen  trierter Schwefelsäume löst und Baumwolle  aus     blaugrüner        liüpe    in echten, schwarz  oliven Tönen färbt.  



  Das dem vorliegenden Verfahren als     Aus-          ,angsprodukt    dienende     Di-(4'-benzoylamino-          1'    -     anthrachinonyl    - )     amirrodinaphthylentIiio-          phen    kann wie     folgt    hergestellt werden:

    2,45 Teile     Dibromdinapllthylenthiophen,          hergestellt    durch     Bromieren    von     Dinaph-          thylenthiophen    in Nitrobenzol bei 80-70  ,  3,7 Teile     1-Amino-4-benzo3@1aminoanthrachi-          non,        1.,5    Teile     wasserfreies        LNatriumcarbonat,     1,5 Teile entwässertes     Natriumacetat    und    0,

  15 Teile     Kupferehlorür    werden in 72 Tei  len     Nitrobenzol        verteilt    und     61i2    Stunden im  Sieden gehalten. Nun wird heiss filtriert, der  Rückstand mit     Nitrobenzol,    Benzol und Al  kohol gewaschen und zur     Reinigung    mit ver  dünnter Salzsäure ausgekocht, filtriert, ge  waschen und     getrocknet.    Man erhält in sehr  guter Ausbeute ein     schwarzes        Pulver,    das  sich in konzentrierter     Schwefelsäure    mit an  fänglich grüner Farbe löst und einen Schmelz  punkt über 400   besitzt.  



  Als     kondensierende    Mittel kommen insbe  sondere diejenigen in Betracht, die zur     Fler-          stellung    von     Rixibschlüssen,    wie     Carbazol-          rings.ehlüssen,        geeignet    sind, wie Aluminium  chlorid,     gegebenenfalls        zusammen    mit     AlkaIi-          haloceniden,        Benzylcyaniden    und Säure  chloriden,     hauptsächlich    aber konzentrierte  Schwefelsäure sowie ihre Abkömmlinge, wie       Chlorsulfonsäure.     



  <I>Beispiel:</I>  8 Teile des     Umsetzunbs-pro,duktes    aus  1     Mo1        Dibromdinaphthylenthiophen    mit 2     Mol              1-Amino-4-benzoylaminoantliracliinon    werden  in 65 Teile 96 ö     ige    Schwefelsäure eingetra  gen und 16 Standen bei 0-5       gerührt.    Dann  gibt man bei dieser     Temperatur    in Portionen  0,6 Teile     Chromsäureanhydrid    zu und rührt  ,weitere 4 Stunden     bei    0-5  . Nun trägt man  in Eis ein, filtriert ab und trocknet oder     ver-          pastet.  



  Additional patent to main patent no. 214180. Process for the production of a nub dye% see It has been found that a valuable Liüpen dye can be produced if di- (4'-benzoyla @ mino-1 '-. Anthraquinony 1-) aminodinaphthylenethiophene, which is obtained by dibrominating dinaphthylenethiophene and replacing dc-r bromine atoms with 1- Amino-4-benzoylaminoanthra, quinone residues is available,

    treated with condensing agents.



  The dye forms a black powder that dissolves in concentrated sulfur fringes with a violet color and dyes cotton from blue-green liüpe in real, black-olive tones.



  The di- (4'-benzoylamino- 1 '- anthraquinonyl -) amirrodinaphthylenethylenephen serving as the starting product for the present process can be prepared as follows:

    2.45 parts of dibromodinapllthylenethiophene, prepared by brominating dinaphthylenethiophene in nitrobenzene at 80-70, 3.7 parts of 1-amino-4-benzo3 @ 1 aminoanthraquinone, 1., 5 parts of anhydrous sodium carbonate, 1.5 parts of dehydrated sodium acetate and 0,

  15 parts of copper chloride are distributed in 72 parts of nitrobenzene and kept at the boil for 61/2 hours. It is then filtered hot, the residue is washed with nitrobenzene, benzene and alcohol and, for cleaning, boiled with dilute hydrochloric acid, filtered, washed and dried. A black powder is obtained in very good yield, which dissolves in concentrated sulfuric acid with a green color and has a melting point of over 400.



  Particularly suitable condensing agents are those which are suitable for the production of connections such as carbazole rings, such as aluminum chloride, optionally together with alkali halocenides, benzyl cyanides and acid chlorides, but mainly concentrated sulfuric acid and theirs Derivatives such as chlorosulfonic acid.



  <I> Example: </I> 8 parts of the conversion product from 1 mol of dibromodinaphthylenethiophene with 2 mol of 1-amino-4-benzoylaminoantliracliinone are introduced into 65 parts of 96% sulfuric acid and 16 levels are stirred at 0-5. Then 0.6 part of chromic anhydride is added in portions at this temperature and the mixture is stirred for a further 4 hours at 0-5. Now it is put into ice, filtered off and dried or pasted.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- fa.rbstoffes, dadurch gekennzeichnet, dass man Di - (T- benzoylamino -<B>l'-</B> anthrachinonyl - ) aminodina.phthy lentliiophen, PATENT CLAIM: Process for the production of a vat dye, characterized in that di - (T-benzoylamino - <B> l'- </B> anthraquinonyl -) aminodina.phthy lentliiophene, das durch Di- bromieren von Dinaplithylenthiophen und Ersatz der Bromatome durch 1-Amino-4- henzoy laminoanthrachinonreste erhältlich ist, mit kondensierenden Mitteln behandelt. Der Farbstoff bildet ein schwarzes Pul ver, which is obtainable by dibrominating dinaplithylene thiophene and replacing the bromine atoms with 1-amino-4-henzoy laminoanthraquinone residues, treated with condensing agents. The dye forms a black powder, das sieh mit violetter Farbe in konzen trierter Schwefelsäure löst und Baumwolle aus blaugrüner Küpe in echten, Schwarz oliven Tönen färbt. UNTERANSPRUCH: Verfahren nach Patentanspruch, gekenn zeichnet durch die Verwendung von konzen trierter Schwefelsäure aJs kondensierendes Mittel. that dissolves with violet color in concentrated sulfuric acid and dyes cotton from a blue-green vat in real, black-olive tones. SUBCLAIM: Method according to claim, characterized by the use of concentrated sulfuric acid as a condensing agent.
CH216596D 1939-04-15 1939-04-15 Process for the production of a vat dye. CH216596A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH216596T 1939-04-15
CH214180T 1939-04-15

Publications (1)

Publication Number Publication Date
CH216596A true CH216596A (en) 1941-08-31

Family

ID=25725561

Family Applications (1)

Application Number Title Priority Date Filing Date
CH216596D CH216596A (en) 1939-04-15 1939-04-15 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH216596A (en)

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