CH212644A - Process for the preparation of a monoazo dye. - Google Patents

Process for the preparation of a monoazo dye.

Info

Publication number
CH212644A
CH212644A CH212644DA CH212644A CH 212644 A CH212644 A CH 212644A CH 212644D A CH212644D A CH 212644DA CH 212644 A CH212644 A CH 212644A
Authority
CH
Switzerland
Prior art keywords
yellow
preparation
dye
methyl
monoazo dye
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH212644A publication Critical patent/CH212644A/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo 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
    • C09B29/3652—Monoazo 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
    • C09B29/366—Monoazo 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Description

  

  Verfahren zur Herstellung eines     Nonoazofarbstoffes.       Es wurde gefunden, dass man zu wert  vollen Pigmentfarbstoffen gelangt, wenn man  die     Diazoverbindungen    aus Aminen von der  allgemeinen Formel  
EMI0001.0003     
    worin     g.    die Gruppe -CO- oder     -SOz-          bezeichnet,        Ri    und     R2        Alkyl-,        Aralkyl-,        Aryl-          reste    oder hydroaromatische Reste bedeuten,

    die noch weiter miteinander unter Bildung  eines     heterooyclischen    Ringsystems verbunden  sein können und wobei der     Benzolrest    a noch  weiter substituiert sein kann durch     Alkyl-,          Alkoxy-,        Aryloxygruppen    oder durch Halogen,  mit     1-Aryl-3-methyl-5-pyrazolonen,        1-Aryl-          3-aryl-5-pyrazolorren,        1-Aryl    - 5     -pyrazolon-3-          carbonsäureestern,    sowie deren     Substitutions-          produkten    kuppelt,

   wobei beide Farbstoff-         komponenten    keine     wasserlöslichmachenden     Gruppen, z. B.     Sulfonsäure-    oder     Carbonsäure-          gruppen,    enthalten sollen.  



  Die neuen     Farbstoffe    färben in lebhaften  gelben und orangen Farbtönen von guten  Echtheitseigenschaften, insbesondere von guter  Lichtechtheit. Sie sind unlöslich in Wasser,  lösen sich dagegen sehr gut in vielen organi  schen Lösungsmitteln, wie z. B. Kohlenwasser  stoffen, Alkoholen, Estern, Betonen und kön  nen daher auch zum Färben dieser Lösungs  mittel, sowie damit hergestellter Lacke, wie  etwa     Nitro-    oder     Acetylcelluloselacke,    Filme  oder Kunstmassen verwendet werden. Auch  zum Färben von     Firnislacken,    Kerzen und  Fetten sind die Produkte vorzüglich brauchbar.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines Mono  azofarbstoffes, welches dadurch gekennzeich  net ist, dass man die     Diazoverbindung    von     1-          Aminobenzol-2-(carboyl-diäthylamin)    mit     1-          Phenyl-3-methyl-5-pyrazolon    kuppelt.

             Peispiel:     <B>9,6</B> Gewichtsteile     1-Aminobettzol    -2 -     (car-          boyl-diäthylamitt)    werden in der üblichen  Weise     diazotiert.    Hierauf versetzt man die       Diazolösung    zur Bindung der überschüssigen       Mineralsäure    mit     Natriumacetat    und rührt  sie in eine wässerige Suspension von 8,7  Gewichtsteilen     1-Phertyl-3-tnethyl-5-pyrazolott     ein, die man durch Lösen dieser     Verbindung     in verdünnter Natronlauge und Fällen mit  Essigsäure erhält.

   Nach Beendigung der Kupp  lung wird der entstandene Farbstoff     abfiltriert,     gut ausgewaschen und getrocknet.  



  Er stellt ein gelbes Pulver dar, das sich  in Aceton,     Butylacetat    und andern organi  schen Lösungsmitteln leicht mit gelber Farbe    löst und     Celluloseesterlacke    in lebhaften und  echten gelben     Tönen    färbt.



  Process for the preparation of a nonoazo dye. It has been found that valuable pigment dyes are obtained if the diazo compounds from amines of the general formula
EMI0001.0003
    wherein g. denotes the group -CO- or -SOz-, Ri and R2 denote alkyl, aralkyl, aryl radicals or hydroaromatic radicals,

    which can be further connected to one another to form a heterooyclic ring system and where the benzene radical a can be further substituted by alkyl, alkoxy, aryloxy groups or by halogen, with 1-aryl-3-methyl-5-pyrazolones, 1-aryl - 3-aryl-5-pyrazolorren, 1-aryl - 5-pyrazolone-3-carboxylic acid esters, as well as their substitution products,

   both dye components have no water-solubilizing groups, e.g. B. sulfonic acid or carboxylic acid groups should contain.



  The new dyes dye in vivid yellow and orange shades with good fastness properties, in particular good lightfastness. They are insoluble in water, but dissolve very well in many organic solvents, such as. B. hydrocarbons, alcohols, esters, concretes and can therefore also be used for coloring these solvents, as well as paints made with them, such as nitro or acetyl cellulose paints, films or synthetic materials. The products can also be used to color varnishes, candles and fats.



  The present patent relates to a process for the preparation of a mono azo dye, which is characterized in that the diazo compound of 1- aminobenzene-2- (carboyl-diethylamine) is coupled with 1-phenyl-3-methyl-5-pyrazolone.

             Example: 9.6 parts by weight of 1-aminobettzene -2 - (carboyl diethylamide) are diazotized in the usual way. Sodium acetate is then added to the diazo solution to bind the excess mineral acid and it is stirred into an aqueous suspension of 8.7 parts by weight of 1-methyl-3-methyl-5-pyrazolite, which is obtained by dissolving this compound in dilute sodium hydroxide solution and precipitating with acetic acid receives.

   After the coupling has ended, the resulting dye is filtered off, washed well and dried.



  It is a yellow powder that easily dissolves in acetone, butyl acetate and other organic solvents with a yellow color and colors cellulose ester coatings in vivid and genuine yellow tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines hLotto- azofarbstoffes, dadureh gekennzeichnet, dass man die Diazoverbindungvori 1-Aminobenzol- 2-(carboyl -diäthyl < ttnitt) mit 1 - Phenyl - 3 methyl-5-pyrazolon kuppelt. PATENT CLAIM: A process for the production of a lotto azo dye, characterized in that the diazo compound is coupled with 1-phenyl-3-methyl-5-pyrazolone before 1-aminobenzene-2- (carboyl-diethyl). Der erhaltene Farbstoff stellt ein gelbes <B>Pulver</B> dar, das sich in Aceton, Butylacetat und andern organischen Lösungsmitteln leicht rillt gelber Farbe löst und Celluloseesterlacke in lebhaften und echten gelben Tönen färbt. The dye obtained is a yellow <B> powder </B> which dissolves in acetone, butyl acetate and other organic solvents in a slightly grooved yellow color and colors cellulose ester coatings in vivid and genuine yellow tones.
CH212644D 1938-06-04 1939-05-17 Process for the preparation of a monoazo dye. CH212644A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE212644X 1938-06-04

Publications (1)

Publication Number Publication Date
CH212644A true CH212644A (en) 1940-12-15

Family

ID=5809129

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212644D CH212644A (en) 1938-06-04 1939-05-17 Process for the preparation of a monoazo dye.

Country Status (1)

Country Link
CH (1) CH212644A (en)

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