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CH308399A - Process for the preparation of a new monoazo dye. - Google Patents

Process for the preparation of a new monoazo dye.

Info

Publication number
CH308399A
CH308399A CH308399DA CH308399A CH 308399 A CH308399 A CH 308399A CH 308399D A CH308399D A CH 308399DA CH 308399 A CH308399 A CH 308399A
Authority
CH
Switzerland
Prior art keywords
chromium
dye
new
preparation
sulfuric acid
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 CH308399A publication Critical patent/CH308399A/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
    • 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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Monoazofarbstoffes.       Es wurde gefunden, dass man     zti    einem  wertvollen, neuen     14Ionoazofarbstoff    gelangt,  wenn man     diazotierte        4-Chlor-2-amino-l-oxy-          benzol-6-sulfonsäure    mit     5-Pyrazolon-3-carbon-          säure-ri-butylamid    vereinigt und den erhalte  nen     Farbstoff    mit chromabgebenden Mitteln  behandelt.  



  Der neue chromhaltige     Farbstoff    löst sich  in Wasser mit reiner blauroter, in konzentrier  ter Schwefelsäure mit bordeauxroter Farbe und  färbt Wolle aus schwefelsaurem Bade in sehr  gleichmässigen, lichtechten, reinen blauroten  Tönen.  



  Die Kupplung erfolgt beim vorliegenden  Verfahren mit Vorteil in alkalischem Medium.  Die Behandlung mit den chromabgebenden Mit  teln wird zweckmässig in wässerigem Medium,  z. B. mit Salzen des dreiwertigen Chroms, und  bei Siedetemperatur des Reaktionsgemisches  durchgeführt.  



  <I>Beispiel:</I>  18,3 Teile     5-Pyrazolon-3-carbonsäure-n-          butylamid    werden in 100 Teilen Wasser und 4  Teilen     Natriumhydroxyd    gelöst und bei 0  mit  der auf üblicher Weise hergestellten, mit N     a-          triumcarbonat    neutralisierten     Diazoverbindung     aus 22,4 Teilen     4-Chlor-2-amino-l-oxybenzol-          6-sulfonsäure    vereinigt. Die Kupplung setzt so  fort ein und wird, indem man die Temperatur  auf 20  steigen lässt, in 10 bis 12 Stunden zu    Ende geführt. Der     Farbstoff    wird     abfiltriert,     mit verdünnter, z.

   B.     5 /oiger        Natriumchlorid-          lösung    gewaschen und getrocknet.  



  4,4 Teile des so erhaltenen     Farbstoffes    wer  den in 200 Teilen Wasser bei Siedetemperatur  gelöst und mit 10 Teilen einer     6 /a    Chrom ent  haltenden     Chromsulfatlösung        (Cr2(S04)31    ver  setzt. Man erhitzt etwa 20 Stunden unter Rück  fluss zum Sieden und isoliert die entstandene  Chromverbindung durch     Aussalzen    und Ab  filtrieren.



  Process for the preparation of a new monoazo dye. It has been found that a valuable, new 14ionoazo dye is obtained if diazotized 4-chloro-2-amino-1-oxybenzene-6-sulfonic acid is combined with 5-pyrazolone-3-carboxylic acid ri-butylamide and the dye obtained is treated with chromium donating agents.



  The new chromium-containing dye dissolves in water with pure blue-red, in concentrated sulfuric acid with a burgundy color and dyes wool from sulfuric acid bath in very even, lightfast, pure blue-red tones.



  In the present process, the coupling is advantageously carried out in an alkaline medium. The treatment with the chrome-releasing means is expediently in an aqueous medium, for. B. with salts of trivalent chromium, and carried out at the boiling point of the reaction mixture.



  <I> Example: </I> 18.3 parts of 5-pyrazolone-3-carboxylic acid-n-butylamide are dissolved in 100 parts of water and 4 parts of sodium hydroxide and neutralized with sodium carbonate at 0 with the one prepared in the usual way Diazo compound from 22.4 parts of 4-chloro-2-amino-1-oxybenzene-6-sulfonic acid combined. The coupling continues immediately and is completed in 10 to 12 hours by allowing the temperature to rise to 20. The dye is filtered off, washed with dilute, z.

   B. 5% sodium chloride solution washed and dried.



  4.4 parts of the dye thus obtained are dissolved in 200 parts of water at boiling temperature and treated with 10 parts of a 6 / a chromium-containing chromium sulfate solution (Cr2 (S04) 31. The mixture is heated to boiling under reflux for about 20 hours and isolated filter the resulting chromium compound by salting out and from.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen DIo- noazofarbstoffes, dadurch gekennzeichnet, da.ss man diazotierte 4-Chlor-2-amino-l-oxybenzol-, 6-sulfonsäure mit 5-Pyrazolon-3-carbonsäure- n-butylamid vereinigt und den erhaltenen Farb stoff mit chromabgebenden Mitteln behandelt. Der neue chromhaltige Farbstoff löst sich in Wasser mit reiner blauroter, in konzentrierter Schwefelsäure mit bordeauxroter Farbe und färbt Wolle aus schwefelsaurem Bade in sehr gleichmässigen, lichtechten, reinen blauroten Tönen. PATENT CLAIM Process for the preparation of a new dionoazo dye, characterized in that diazotized 4-chloro-2-amino-1-oxybenzene, 6-sulfonic acid is combined with 5-pyrazolone-3-carboxylic acid n-butylamide and the resulting Dye treated with chromium-releasing agents. The new chromium-containing dye dissolves in water with pure blue-red, in concentrated sulfuric acid with a burgundy color and dyes wool from sulfuric acid bath in very even, lightfast, pure blue-red tones. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man als chromabgebende Mittel Salze des dreiwertigen Chroms ver wendet. -_ SUBCLAIM: Process according to claim, characterized in that salts of trivalent chromium are used as chromium-releasing agents. -_
CH308399D 1951-12-15 1951-12-15 Process for the preparation of a new monoazo dye. CH308399A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH308399T 1951-12-15
CH305714T 1951-12-15

Publications (1)

Publication Number Publication Date
CH308399A true CH308399A (en) 1955-07-15

Family

ID=25734967

Family Applications (1)

Application Number Title Priority Date Filing Date
CH308399D CH308399A (en) 1951-12-15 1951-12-15 Process for the preparation of a new monoazo dye.

Country Status (1)

Country Link
CH (1) CH308399A (en)

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