CH140013A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH140013A
CH140013A CH140013DA CH140013A CH 140013 A CH140013 A CH 140013A CH 140013D A CH140013D A CH 140013DA CH 140013 A CH140013 A CH 140013A
Authority
CH
Switzerland
Prior art keywords
preparation
azo dye
oxy
amino
nitro
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH140013A publication Critical patent/CH140013A/en

Links

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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
    • C09B45/40—Chromium compounds
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium

Landscapes

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

Description

  

  Zusatzpatent zum Hauptpatent     Nr.   <B>137741.</B>         Terfahren    zur     Barsteilung    eines     Azofarbstoffes.            Pyrazolone    von     4'-Amino,-4-oxy-diplienyl-          met'ha--u3-e,a,rbeim,äuren,        bezw.    ihren Deri  vaten, sind bis jetzt zur Darstellung von       Azofarbün    nicht benützt Worden.

   Es  wurde gefunden,     dass    man aus solchen     Py-          razolonen        naehehromierbare,        Azofarbstoffe     .erhält, deren Färbungen durch die     vorzüg-          liehen    Echtheitseigenschaften auffallen. Spe-         ziell    erwähnenswert ist die hervorragende  Lichtechtheit.  



  Das vorliegende, Verfahren ist dadurch  gekennzeichnet,     dass    das     2-Diazo-4-nitro-l-          phenol    mit dem     Methylpyrazolan    aus     4'-          Amino-4-oxy-diphenylmetha,n-3-earbonsiLure     der Formel  
EMI0001.0024     
    gekuppelt wird.    Das erhaltene Produkt färbt auf Wolle.

         nao,he,hro-miert,    ein etwas     bräunliehes    Orange  von ganz hervorragenden     Echtheiten.       <I>Beispiel:</I>    15,4 Teile     2-Amino-4-nitro-l-phenol    wer  den     diazotiert    und mit     32,4    Teilen des,     Me-          thylpyrazolons    aus     4'-Amino-4-oxy-diphenyl-          inet,ha,n-3-earbonsä,ure    in     sodaalkalischer    Lö-         sung    gekuppelt. Ist die Kupplung beendet,  so wird     ausgesalzen    und getrocknet.  



  Der Farbstoff ist ein     braun-es    Pulver, das  Wolle aus saurer Lösung braungelb färbt  und beim     Nachchromieren    in ein bräunliches  Orange übergeht von ganz hervorragenden       Echtheiten.     



  Das     Metliylpyra-zolon    aus     4'-Amino.4-          oxy-diplienylmethan-3-earbonsä,ure    wird er  halten durch Behandeln der entsprechenden       Diazoverbindung    mit     Sulfit    nach bekannter      Methode und Kondensation der     4-Hydrazilio-          4-#oxy-diphenylmetlian-3-earbonsä.ure    mit       Aceteossigester    in     es"sigsaurer    Lösung. Das       Pyrazolon    ist ein helles Pulver>     clas    in wässe  rigen Alkalien, sowie     Natriumacetatlösung     <B>k2</B>  leicht     löslieli    ist.



  Additional patent to main patent no. <B> 137741. </B> Terfahren for the bar division of an azo dye. Pyrazolones of 4'-amino, -4-oxy-diplienyl- met'ha - u3-e, a, rbeim, äuren, respectively. their derivatives have not yet been used to represent azo color.

   It has been found that such pyrazolones are obtained from such pyrazolones, azo dyes whose colorations are noticeable due to their excellent fastness properties. The excellent lightfastness is particularly worth mentioning.



  The present process is characterized in that the 2-diazo-4-nitro-1-phenol with the methylpyrazolane from 4'-amino-4-oxy-diphenylmetha, n-3-carboxylic acid of the formula
EMI0001.0024
    is coupled. The product obtained stains wool.

         nao, hey, hro-miert, a somewhat brownish orange with excellent fastness properties. <I> Example: </I> 15.4 parts of 2-amino-4-nitro-l-phenol are diazotized and mixed with 32.4 parts of methylpyrazolone from 4'-amino-4-oxy-diphenyl inet, ha, n-3-earbonsä, ure coupled in a soda-alkaline solution. Once the coupling has ended, it is salted out and dried.



  The dye is a brown powder that dyes wool from an acidic solution to a brownish-yellow color and turns into a brownish orange when it is chromed and has excellent fastness properties.



  The methylpyrazolone from 4'-Amino.4-oxy-diplienylmethane-3-carboxylic acid is obtained by treating the corresponding diazo compound with sulfite by a known method and condensing the 4-hydrazilio-4- # oxy-diphenylmetlian-3- Acetic acid with acetic acid ester in an acidic solution. The pyrazolone is a pale powder that is easily soluble in aqueous alkalis and sodium acetate solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines; Azofarb- stolfes, dadurch gekennzeichnet, dass das 2- Diazo-4-nitro-l-phenol mit dem Methyl-pyra- zolon aus 4'-Amino,-4-oxy-diphenylmethan-3- carbonsäure der Formel EMI0002.0019 "ekuppelt a wird. Das erhaltene Produkt, färbt auf Wolle, nachehromiert, PATENT CLAIM: Method for the representation of a; Azofarb- stolfes, characterized in that the 2-diazo-4-nitro-1-phenol with the methyl-pyrazolone from 4'-amino, -4-oxy-diphenylmethane-3-carboxylic acid of the formula EMI0002.0019 "ekuppelt a is. The product obtained, dyes on wool, nachehromiert, ein etwas bräunlic'hes Orange <B>in</B> von ganz hervoragenden Eehtheiten. a slightly brownish orange <B> in </B> of very excellent whiteness.
CH140013D 1928-07-30 1928-07-30 Process for the preparation of an azo dye. CH140013A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH137741T 1928-07-30
CH140013T 1928-07-30

Publications (1)

Publication Number Publication Date
CH140013A true CH140013A (en) 1930-05-15

Family

ID=25713041

Family Applications (1)

Application Number Title Priority Date Filing Date
CH140013D CH140013A (en) 1928-07-30 1928-07-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH140013A (en)

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