CH272498A - Process for the preparation of a monoazo dye. - Google Patents

Process for the preparation of a monoazo dye.

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Publication number
CH272498A
CH272498A CH272498DA CH272498A CH 272498 A CH272498 A CH 272498A CH 272498D A CH272498D A CH 272498DA CH 272498 A CH272498 A CH 272498A
Authority
CH
Switzerland
Prior art keywords
yellow
dye
preparation
parts
carboxylic 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 CH272498A publication Critical patent/CH272498A/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
    • 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

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

Description

  

  Verfahren zur Herstellung eines     Monoazofarbstoffes.       Es wurde     gefunden,    dass     man    zu einem  wertvollen     Monoazofarbstoff    gelangt, wenn  man     diazotierte        2-Aminobenzol-5-sulfonsäure-          diäthylainid,-1-        carbonsäure    mit 1- (3'-     Sulf-          amido)-plienyl-3-methyl-5-pyrazolon    vereinigt.  



  her neue Farbstoff stellt in trockenem  Zustand eine orangegelbe Substanz dar, die  sich in heissem     Wasser    und heisser     Natrium-          carbonatlösung    mit gelber Farbe löst und  Wolle aus saurem Bade in gelben Tönen  färbt, die beim     Nachchromieren        braunstichig          gelb        und        sehr        gut        wasch-,        walk-        und     werden. Der Farbstoff eignet sich auch  hervorragend zum Färben nach dem Ein  badchromierverfahren.  



  Die beim vorliegenden Verfahren als Aus  gangsstoff dienende     2-Aminobenzol-5-sulfon-          säure-diätliylamid-l-carbonsäure    kann nach  üblichen, an sieh bekannten     :Methoden    herge  stellt werden, z. B. indem man     2-Chlorbenzol-          5-sulfonsäurechlorid-l-carbonsäure    mit     Di-          äthylamin    umsetzt und in der erhaltenen       2-Clilorbenzol-5-sulfonsäure-diäthy        lamid-l-car-          bonsäure    das Chloratom durch die     -NH..-          Gruppe        ersetzt.     



  Die     Diazotierung    der     2-Aminobenzol-5-sul-          Consäure-diätliylamid-l-carbonsäure    kann eben  falls nach an sieh bekannten     Metboden    erfol  gen, mit Vorteil     naeli    der sogenannten indi  rekten Methode, d.     1i.    dadurch, dass man eine  Lösung, die ein     Alkalisalz    der     Diazotierungs-          komponente    sowie die erforderliche Menge Ni  trit enthält, mit einer einen     Ubersehuss    über    die theoretisch benötigte Menge Säure ent  haltenden, verdünnten     Salzsäurelösung    ver  einigt.  



  Die Kupplung wird beim vorliegenden  Verfahren mit Vorteil in alkalischem     1@Iediuni          durchgeführt..    Hierbei kann man z. B. so vor  gehen, dass man das     1-(3'-Sulfamido)-phenyl-          3-methvl-5-py        razolon    mit der erforderlichen       1,Ienge        Alkalihydroxyd    löst und den für die       Kupplung    benötigten     Alkaliübersehuss    in  Form eines     Alkalicarbonates    hinzufügt. Ge  gebenenfalls kann die Kupplung auch unter  Zusatz neutraler oder basischer Lösungs  mittel wie z. B.

   Alkohol,     Pyridin,    Äthanol  amin usw. erfolgen.  



       Beispiel:     <B><U>27,2</U></B> Teile     '-Aminobenzol-5-sulfonsäure-          diäthylamid-l-earbonsäure    werden in 300 Tei  len Wasser unter Zusatz von 8 Teilen wasser  freiem     Natriumearbonat    gelöst.

   Nachdem man  7 Teile     Natriumnitrit    hinzugefügt hat, lässt  man diese Lösung zu einem aus     .10    Teilen  30      /oiger        Salzsäure        lind    so viel Fis beste  henden Gemisch zufliessen, dass während der       Diazotierun-    die Reaktionstemperatur etwa  10 bis 15  beträgt, und rührt bis zur     Beendi-          ,un,    der     Diazotierung.    Die Suspension der       Diazov        erbindung    wird mit einer Lösung von  25,3 Teilen     1-(3'-Sulfamido)

  -phenyl-3-met.hyl-          5-pyra.zolon    in 200 Teilen Wasser, 6 Teilen  N     atriumhvdroYV    d und 25 Teilen wasserfreiem  N     atriumcarbonat    bei 5 bis 10  vereinigt. Man  rührt bis zur Beendigung der     Kupplung    und      filtriert den Farbstoff ab. Er kann zur wei  teren Reinigung nochmals in Wasser ver  rührt und wieder     abfiltriert    werden.



  Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 2-aminobenzene-5-sulfonic acid diethylainide, -1-carboxylic acid with 1- (3'-sulfamido) -plienyl-3-methyl-5-pyrazolone is used united.



  Her new dye is an orange-yellow substance when dry, which dissolves in hot water and a hot sodium carbonate solution with a yellow color and dyes wool from an acid bath in yellow tones, which is brownish yellow when re-chrome-plated and is very easy to wash, mill and will. The dye is also ideal for dyeing using the one bath chrome plating process.



  The 2-aminobenzene-5-sulfonic acid diätliylamid-l-carboxylic acid used as starting material in the present process can be prepared according to conventional methods known per se, eg. B. by reacting 2-chlorobenzene-5-sulfonic acid chloride-1-carboxylic acid with diethylamine and in the 2-chlorobenzene-5-sulfonic acid diethylamide-l-carboxylic acid obtained the chlorine atom through the -NH ..- group replaced.



  The diazotization of the 2-aminobenzene-5-sul- consäure-dietliylamid-1-carboxylic acid can also take place according to methods known per se, with advantage using the so-called indirect method, ie. 1i. by combining a solution containing an alkali salt of the diazotization component and the required amount of Ni trite with a dilute hydrochloric acid solution containing an excess of the theoretically required amount of acid.



  In the present process, the coupling is advantageously carried out in an alkaline 1 @ Iediuni. B. go before that one dissolves the 1- (3'-sulfamido) -phenyl- 3-methvl-5-py razolon with the required 1, Lenght alkali hydroxide and adds the excess alkali required for the coupling in the form of an alkali carbonate. Ge optionally the coupling can also medium with the addition of neutral or basic solvents such. B.

   Alcohol, pyridine, ethanol amine, etc. take place.



       Example: Parts of aminobenzene-5-sulfonic acid diethylamide-1-carboxylic acid are dissolved in 300 parts of water with the addition of 8 parts of anhydrous sodium carbonate.

   After 7 parts of sodium nitrite have been added, this solution is added to a mixture consisting of .10 parts of 30% hydrochloric acid and so much Fis that the reaction temperature is about 10 to 15 during the diazotization, and the mixture is stirred until the end. , un, the diazotization. The suspension of the Diazov compound is mixed with a solution of 25.3 parts of 1- (3'-sulfamido)

  -phenyl-3-met.hyl-5-pyra.zolon in 200 parts of water, 6 parts of sodium hydroxide and 25 parts of anhydrous sodium carbonate at 5 to 10 combined. The mixture is stirred until the coupling has ended and the dye is filtered off. For further purification, it can be stirred again in water and filtered off again.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines 1VIono- azofarbstoffes, dadurch gekennzeichnet, dass man diazotierte 2-Aminobenzol-5-sulfonsäure- diäthylamid-l-earbonsäure mit 1-(3'-Sulf- amido)-pbenyl-3-methyl-5-pyrazolon vereinigt. PATENT CLAIM: A process for the preparation of a 1Viono azo dye, characterized in that diazotized 2-aminobenzene-5-sulfonic acid diethylamide-1-carboxylic acid with 1- (3'-sulfamido) -pbenyl-3-methyl-5-pyrazolone united. Der neue Farbstoff stellt in trockenem Zu stand eine orangegelbe Substanz dar, die sich in heissem Wasser und heisser Natriumearbo- natlösung mit gelber Farbe löst und Zolle aus saurem Bade in gelben Tönen färbt, die beim Nachehromieren braunstickig gelb und sehr gut wasch-, walk- und liehtecht werden. Der Farbstoff eignet sich aueh hervorragend zum Färben nach dem Einbadehromierver- fahren. When dry, the new dye is an orange-yellow substance that dissolves in hot water and hot sodium carbonate solution with a yellow color and colors Zolle in acidic baths in yellow tones, which when re-homing are brownish-yellow and very easy to wash, whip. and be borrowed. The dye is also excellently suited for dyeing using the single-bath homing method.
CH272498D 1948-02-12 1948-02-12 Process for the preparation of a monoazo dye. CH272498A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272498T 1948-02-12
CH270539T 1948-12-13

Publications (1)

Publication Number Publication Date
CH272498A true CH272498A (en) 1950-12-15

Family

ID=25731209

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272498D CH272498A (en) 1948-02-12 1948-02-12 Process for the preparation of a monoazo dye.

Country Status (1)

Country Link
CH (1) CH272498A (en)

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