CH160958A - Process for the production of a vat dye of the anthraquinone series. - Google Patents

Process for the production of a vat dye of the anthraquinone series.

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Publication number
CH160958A
CH160958A CH160958DA CH160958A CH 160958 A CH160958 A CH 160958A CH 160958D A CH160958D A CH 160958DA CH 160958 A CH160958 A CH 160958A
Authority
CH
Switzerland
Prior art keywords
production
dye
parts
mol
anthraquinone series
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
Priority to CH160958D priority Critical patent/CH160958A/en
Publication of CH160958A publication Critical patent/CH160958A/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
    • C09B5/28Anthrimide carbazoles

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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 Nr. 156755.    Verfahren zur Herstellung eines     Iiüpenfarbstoifes    der     Anthr        aehinonr        eihe.       Es wurde gefunden, dass man einen  neuen     Küpenfarbstoff    der     Anthrachinon-          reihe    erhält, wenn man auf 2     Mol        1,3-          Dihalogenanthrachinon    nacheinander 1     Mol          1,4-Diaminoanthrachinon    und 2.

       Mol    1  Aminoanthrachinon einwirken lässt und  hierauf das erhaltene Produkt mit einem  sauren Kondensationsmittel behandelt.  



  Der neue Farbstoff stellt ein dunkles  Pulver dar, das sich in konzentrierter  Schwefelsäure mit rötlich braunschwarzer  Farbe löst und Baumwolle aus der     Küpe    in  sehr echten, schwärzlich oliven Tönen färbt.  <I>Beispiel:</I>  23,8 Teile     1,4-Diaminoanthrachinon,    74  Teile     1,3-Dibromanthrachinon,    25 Teile was  serfreies     Natriumacetat,    1 Teil Kupferacetat  und 800 Teile Nitrobenzol werden 10 Stun  den zum Sieden erhitzt. Das Umsetzungs  produkt wird kalt     abfiltriert,    mit     Nitro-          benzol,    dann mit Alkohol gewaschen, hierauf  mit Wasser ausgekocht und getrocknet.

      30 Teile der so erhaltenen Verbindung,  die noch etwa<B>16%</B> Brom enthält, werden  nun mit 20 Teilen     1-Aminoanthrachinon;     5 Teilen wasserfreiem     Natriumacetat,    10  Teilen Soda,. 1 Teil     Kupferchlorür    und       60'0    Teilen     Nitrobenzol   <B>2!2</B> Stunden zum  Sieden erhitzt. Das Umsetzungsprodukt wird  bei etwa<B>1010'</B>     abfiltriert.    Es löst sich in  Monohydrat mit rein grüner Farbe; beim  Austragen auf Wasser erhält man violett  braune Flocken.  



  10 Teile dieser Verbindung werden     nun     bei etwa<B>100'</B> in eine Schmelze eingetragen,  die erhalten wird, indem 20 Teile wasser  freies Aluminiumchlorid derart zu 40 Teilen       Pyridin    gegeben werden, dass die Tempera  tur<B>100'</B> nicht wesentlich übersteigt. Hier  auf wird die Temperatur bis zum schwachen  Sieden des     Pyridins    gesteigert.

   Nach einer  Stunde wird die Schmelze auf eine alkalische       Natriumhydrosulfitlösung    ausgetragen, wo  bei der neue Farbstoff mit gelbbrauner Farbe  in Lösung geht; man filtriert von wenig           unverküpbaren    Anteilen ab und scheidet aus  dem Filtrat durch kräftiges Umrühren an  der Luft bei gewöhnlicher     Temperatur    den  Farbstoff ab und isoliert ihn durch Fil  tration.  



       Zum    selben Farbstoff gelangt man, wenn  statt     1,3-Dibromanthrachinon    das     1,3-Di-          chloranthrachinon    oder das     1-Chlor-3-brom-          anthrachinon    verwendet wird.  



  Ebenso wird dasselbe Resultat erhalten,  wenn das     Natriumacetat    durch     Kaliumacetat     oder     calcinierte        Alkalikarbonate    oder     Magne-          siumogyd    und das Kupferacetat oder Kupfer  chlorür durch andere     Kupferverbindungen     oder metallisches Kupfer ersetzt wird. End  lich wird ebenfalls dasselbe Resultat erhal  ten, wenn als Lösungsmittel statt     Nitro-          benzol    Naphthalin verwendet wird.



      Additional patent to the main patent No. 156755. Process for the production of an anthracite series. It has been found that a new vat dye of the anthraquinone series is obtained if 1 mole of 1,4-diaminoanthraquinone and 2 moles of 1,3-dihaloanthraquinone are successively added.

       Mol 1 Aminoanthraquinone can act and then treated the product obtained with an acidic condensing agent.



  The new dye is a dark powder that dissolves in concentrated sulfuric acid with a reddish brown-black color and dyes cotton from the vat in very real, blackish-olive tones. <I> Example: </I> 23.8 parts of 1,4-diaminoanthraquinone, 74 parts of 1,3-dibromoanthraquinone, 25 parts of water-free sodium acetate, 1 part of copper acetate and 800 parts of nitrobenzene are heated to boiling for 10 hours. The reaction product is filtered off cold, washed with nitrobenzene and then with alcohol, then boiled with water and dried.

      30 parts of the compound thus obtained, which still contains about 16% bromine, are now mixed with 20 parts 1-aminoanthraquinone; 5 parts of anhydrous sodium acetate, 10 parts of soda ,. Heat 1 part copper chloride and 60'0 parts nitrobenzene <B> 2! 2 </B> hours to the boil. The reaction product is filtered off at about <B> 1010 '</B>. It dissolves in monohydrate with a pure green color; when discharged onto water, violet-brown flakes are obtained.



  10 parts of this compound are now introduced into a melt at about <B> 100 '</B>, which is obtained by adding 20 parts of anhydrous aluminum chloride to 40 parts of pyridine in such a way that the temperature is <B> 100' < / B> does not significantly exceed. Here on the temperature is raised to the low boiling point of the pyridine.

   After one hour, the melt is poured onto an alkaline sodium hydrosulfite solution, where the new yellow-brown dye dissolves; it is filtered off from a little unlinkable components and separates from the filtrate by vigorous stirring in the air at ordinary temperature from the dye and isolated it by Fil tration.



       The same dye is obtained if 1,3-dichloroanthraquinone or 1-chloro-3-bromo-anthraquinone is used instead of 1,3-dibromoanthraquinone.



  Likewise, the same result is obtained if the sodium acetate is replaced by potassium acetate or calcined alkali metal carbonates or magnesium oxide, and the copper acetate or copper chloride by other copper compounds or metallic copper. Finally, the same result is obtained if naphthalene is used as solvent instead of nitrobenzene.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Kü- penfarbstoffes der Anthrachinonreihe, dadurch gekennzeichnet, dass man auf 2 Mol 1,3 Dihalogenanthrachinon nacheinander 1 Mol 1,4-Diaminoanthrachinon und 2 Mol 3- Aminoanthrachinon einwirken lässt und hierauf das erhaltene Produkt mit einem sauren Kondensationsmittel behandelt. Claim: A process for the production of a new vat dye of the anthraquinone series, characterized in that 1 mol of 1,4-diaminoanthraquinone and 2 mol of 3-aminoanthraquinone are allowed to act in succession on 2 mol of 1,3 dihaloanthraquinone and then the product obtained is allowed to act with an acidic condensing agent treated. Der neue Farbstoff stellt ein dunkles Pulver dar; das sich in konzentrierter Schwefelsäure mit rötlich braunschwarzer Farbe löst und Baumwolle aus der Küpe in sehr echten, schwärzlich oliven Tönen färbt. The new dye is a dark powder; which dissolves in concentrated sulfuric acid with a reddish brown-black color and dyes cotton from the vat in very real, blackish olive tones.
CH160958D 1931-07-02 1931-07-02 Process for the production of a vat dye of the anthraquinone series. CH160958A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH160958D CH160958A (en) 1931-07-02 1931-07-02 Process for the production of a vat dye of the anthraquinone series.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH156755T 1931-07-02
CH160958D CH160958A (en) 1931-07-02 1931-07-02 Process for the production of a vat dye of the anthraquinone series.

Publications (1)

Publication Number Publication Date
CH160958A true CH160958A (en) 1933-03-31

Family

ID=25716836

Family Applications (1)

Application Number Title Priority Date Filing Date
CH160958D CH160958A (en) 1931-07-02 1931-07-02 Process for the production of a vat dye of the anthraquinone series.

Country Status (1)

Country Link
CH (1) CH160958A (en)

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