CH270834A - Process for the preparation of a monoazo dye. - Google Patents

Process for the preparation of a monoazo dye.

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Publication number
CH270834A
CH270834A CH270834DA CH270834A CH 270834 A CH270834 A CH 270834A CH 270834D A CH270834D A CH 270834DA CH 270834 A CH270834 A CH 270834A
Authority
CH
Switzerland
Prior art keywords
methyl
dye
pyrazolone
preparation
sulfo
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 CH270834A publication Critical patent/CH270834A/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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/34Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     Monoazofarbstoffes.       Es wurde gefunden,     daB    man zu neuen,       wert-v    ollen     Monoazofarbstoffen    der     Pyrazolon-          reihe    gelangt, wenn man     Diazoverbindungen     von Aminen der Formel  
EMI0001.0008     
    mit     Pyrazolonen    der Formel.  
EMI0001.0010     
         vereinigt,    worin R einen aromatischen Rest  der     Benzolreihe    bedeutet.  



  Als     Diazoverbindungen    kommen bei  spielsweise     2-Amino-4,4'-dichlor-1,1'-diphe-          nyläther    oder     2-Amino-4,2'-dichlor-1,1'-di-          phenyläther    in Betracht.  



       i    Als     Pyrazolone    können zum Beispiel ver  wendet werden:     1-(2'-Methyl-4'-sulfo)-phe-          nyl-3-methyl-5-pyrazolon,        1-(2'-Chlor    -5'-         sulfo)-phenyl-3-methyl-5-pyrazolon,    1-(2',5'       Dichlor-4'-sulfo)-phenyl-3-methyl-5-pyrazo-          lon,1-        (3'-Sulfo)        -phenyl-3-methyl-5-pyrazo-          lon    oder     1-(4'-Sulfo)-phenyl-3-methyl-5-pyr-          azolon.     



  Die     Diazotierung    der Amine der eingangs  erwähnten Formel kann nach üblichen, an  sich bekannten Methoden, zum Beispiel mit       Natriumnitrit    in Gegenwart von Salzsäure  erfolgen.  



  Die Kupplung     kann@in    saurem bis alka  lischem Medium durchgeführt werden. Eine  zweckmässige Ausführungsform der Kupp  lung besteht darin, die mineralsauer reagie  rende     Diazolösung    mit der neutral bis schwach       alkalisch    reagierenden Lösung des Natrium  salzes der     Pyrazolonverbindung    zu vereinigen  und dem so erhaltenen Gemisch bis zum Ver  schwinden der mineralsauren Reaktion Na  triumacetat     oderNatriumcarbonat    zuzusetzen.  



  Die so erhältlichen     Monoazofarbstoffe    der       Pyrazolonreihe    entsprechen der allgemeinen  Formel  
EMI0001.0040     
      worin R     einen    aromatischen Rest der     Benzol-          reihe    bedeutet.  



  Diese     Farbstoffe    eignen sich zum Färben  und     Bedrucken    verschiedener Materialien,       insbesondere    solcher tierischer Herkunft wie  Seide, Leder und vor allem Wolle. Die mit  diesen Farbstoffen auf Wolle erzeugten Fär  bungen zeichnen sich durch sehr gute     Wasch-          und    Lichtechtheit aus. Mit den neuen Farb  stoffen können ferner auch     animalisierte        Cel-          lulose,    Kunstfasern aus Casein, Kunstfasern  aus     Superpolyamiden    und     Superpolyuretha-          nen    usw. gefärbt werden.  



  Gegenstand des     vorliegenden    Patentes bil  det ein Verfahren zur Herstellung eines     Mono-          azofarbstoffes,    welches dadurch gekennzeich  net ist, dass man     diazotierten        2-Amino-4,2'-          dichlor-1,1'-diphenyläther        mit        1-(2'-Methyl-          4'-sulfo)-phenyl-3-methyl-5-pyrazolon    kup  pelt.  



  Der neue     Farbstoff    bildet     ein    helles, gelb  braunes Pulver, das sich in heissem Wasser  leicht löst und Wolle aus essigsaurem Bade in  etwas     grünstichig    gelben Tönen von     sehr    gu  ter Lichtechtheit und guten     Nassechtheiten     anfärbt.     In.    konzentrierter Schwefelsäure er  hält man mit diesem Farbstoff eine     bräun-          lichrote    Lösung.

           Beispiel:     Man     diazotiert    25,4     Teile        2-Amino-4,2'-          dichlor    - 1,1' -     diphenyläther    mit 25 Teilen    30%iger Salzsäure und 6,9 Teilen Natrium  nitrit in 200 Teilen Wasser bei     0-5         in    üb  licher Weise.

   Die von Verunreinigungen     ab-          filtrierte        Diazolösung    tropft man bei     0-5      zu einer Lösung, die man aus 200 Teilen Was  ser und 26,8     Teilen        1-(2'-,.Uethyl-4'-sulfo)-phe-          nyl-3-methyl-5-pyrazolon    unter Zusatz von  so     viel        Natriumcarbonat,    dass auf Brillant  gelbpapier schwach     alkalische    Reaktion ein  tritt, erhalten hat.

       Mit    Vorteil setzt man hier  auf     Natriumacetat    oder     Natriumcarbonat    bis  zum     Verschwinden    der mineralsauren Reak  tion zu. Nach beendeter Kupplung wird mit       Natriumcarbonat    oder     Natriumhydroxyd    ver  setzt, bis die Suspension     phenolphthalein-          alkalisch    reagiert. Der Farbstoff wird nun       abfiltriert    und getrocknet.



  Process for the preparation of a monoazo dye. It has been found that new, valuable monoazo dyes of the pyrazolone series are obtained if diazo compounds of amines of the formula
EMI0001.0008
    with pyrazolones of the formula.
EMI0001.0010
         combined, wherein R is an aromatic radical of the benzene series.



  Suitable diazo compounds are, for example, 2-amino-4,4'-dichloro-1,1'-diphenyl ether or 2-amino-4,2'-dichloro-1,1'-diphenyl ether.



       i The following pyrazolones can be used, for example: 1- (2'-methyl-4'-sulfo) -phenyl-3-methyl-5-pyrazolone, 1- (2'-chloro -5'-sulfo) - phenyl-3-methyl-5-pyrazolone, 1- (2 ', 5' dichloro-4'-sulfo) -phenyl-3-methyl-5-pyrazolone, 1- (3'-sulfo) -phenyl-3 -methyl-5-pyrazolone or 1- (4'-sulfo) -phenyl-3-methyl-5-pyrazolone.



  The amines of the formula mentioned at the outset can be diazotized by customary methods known per se, for example with sodium nitrite in the presence of hydrochloric acid.



  The coupling can be carried out in an acidic to alkaline medium. An expedient embodiment of the coupling consists in combining the mineral acid-reactive diazo solution with the neutral to slightly alkaline solution of the sodium salt of the pyrazolone compound and adding sodium acetate or sodium carbonate to the resulting mixture until the mineral acid reaction disappears.



  The monoazo dyes of the pyrazolone series obtainable in this way correspond to the general formula
EMI0001.0040
      where R is an aromatic radical of the benzene series.



  These dyes are suitable for dyeing and printing various materials, especially those of animal origin such as silk, leather and, above all, wool. The dyeings produced with these dyes on wool are characterized by very good wash and lightfastness. The new dyes can also be used to color animalized cellulose, synthetic fibers made from casein, synthetic fibers made from super polyamides and super polyurethanes, etc.



  The subject of the present patent bil det a process for the preparation of a monoazo dye, which is characterized in that diazotized 2-amino-4,2'-dichloro-1,1'-diphenyl ether with 1- (2'-methyl- 4'-sulfo) -phenyl-3-methyl-5-pyrazolone kup pelt.



  The new dye forms a light, yellow-brown powder which dissolves easily in hot water and dyes wool from an acetic acid bath in slightly greenish yellow shades of very good lightfastness and good wetfastness. In. concentrated sulfuric acid, this dye gives a brownish-red solution.

           Example: 25.4 parts of 2-amino-4,2'-dichloro-1,1'-diphenyl ether are diazotized with 25 parts of 30% strength hydrochloric acid and 6.9 parts of sodium nitrite in 200 parts of water at 0-5 in usual Wise.

   The diazo solution filtered off from impurities is added dropwise at 0-5 to a solution which is composed of 200 parts of water and 26.8 parts of 1- (2 '-,. Uethyl-4'-sulfo) -phenyl-3 -methyl-5-pyrazolone with the addition of so much sodium carbonate that a weakly alkaline reaction occurs on brilliant yellow paper.

       It is advantageous to use sodium acetate or sodium carbonate until the mineral acid reaction disappears. When the coupling is complete, sodium carbonate or sodium hydroxide is added until the phenolphthalein suspension gives an alkaline reaction. The dye is then filtered off and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Monoazo- farbstoffes, dadurch gekennzeichnet, dass man diazotierten 2-Amino-4,2'-dichlor-1,1'-diphe- nyläther mit 1-(2'-Methyl-4'-sulfo)-phenyl-3- methyl-5-pyrazolon kuppelt. PATENT CLAIM: Process for the preparation of a monoazo dye, characterized in that diazotized 2-amino-4,2'-dichloro-1,1'-diphenyl ether with 1- (2'-methyl-4'-sulfo) - phenyl-3-methyl-5-pyrazolone couples. - Der neue Farbstoff bildet ein helles, gelb braunes Pulver, das sich in heissem Wasser leicht löst und Wolle aus essigsaurem Bade in etwas grünstichig gelben Tönen von sehr gu ter Lichtechtheit und guten Nassechtheiten anfärbt. In konzentrierter Schwefelsäure er hält man mit diesem Farbstoff eine bräun lichrote Lösung. - The new dye forms a light, yellow-brown powder which dissolves easily in hot water and dyes wool from an acetic acid bath in slightly greenish yellow shades of very good lightfastness and good wetfastness. In concentrated sulfuric acid you get a brownish red solution with this dye.
CH270834D 1949-03-10 1949-03-10 Process for the preparation of a monoazo dye. CH270834A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH270834T 1949-03-10

Publications (1)

Publication Number Publication Date
CH270834A true CH270834A (en) 1950-09-30

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ID=4477934

Family Applications (1)

Application Number Title Priority Date Filing Date
CH270834D CH270834A (en) 1949-03-10 1949-03-10 Process for the preparation of a monoazo dye.

Country Status (1)

Country Link
CH (1) CH270834A (en)

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