CH270538A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH270538A
CH270538A CH270538DA CH270538A CH 270538 A CH270538 A CH 270538A CH 270538D A CH270538D A CH 270538DA CH 270538 A CH270538 A CH 270538A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
orange
parts
chloro
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 CH270538A publication Critical patent/CH270538A/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
    • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28—Amino naphthols
    • C09B29/30—Amino naphtholsulfonic acid
    • 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
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/16—Naphthol-sulfonic acids
    • 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

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

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotierten        -I'-Tertiäramy1-4-ehlor-2-aminodi-          pheny        läther    mit     '?-Oxynaplithalin-6,8-disul-          fonsäure        vereinigt.     



  Der neue Farbstoff bildet ein oranges Pul  ver, das sich in Wasser mit oranger Farbe löst  und Wolle aus     essigsaurem    Bade in orangen  Tönen färbt..  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-4-ehlor-2-          aminodililienyläther    kann     naeli    an sieh be  kannter Methode     dureh    Kondensation von 4  Tertiäramyl-l-oxybenzol mit     1,4-Dichlor-2-ni-          trobenzol    und     naehfolgende    Reduktion der  Nitrogruppe des erhaltenen     4'-Tertiäramyl-4--          chlor-2-nitrodiphenyläthers    zur     Aminogruppe     hergestellt werden.  



  Die     Diazotierung    kann ebenfalls nach be  kannten, für schwer     diazotierbare    Amine     übli-          ehen        -Methoden,    beispielsweise in Gegenwart  von Alkohol oder Essigsäure oder mit Hilfe  von     Nitrosylseliwefelsäure        durehgefübrt    wer  den.  



  Die Kupplung erfolgt mit, Vorteil in     alka-          lisehem,    vorzugsweise     a.lkalicarbonatalkali-          schem        -Medium,        gewünschtenfalls    unter Ver  wendung geeigneter, die Kupplungsreaktion  befördernder Zusätze, wie Alkohol,     Pyridin     usw.

      <I>Beispiel:</I>       11-,5    Teile     4'-Tertiäramyl--l-chlor-2-amino-          diplienylätlier    werden in 50 Teilen     100o/oiger          Essigsäure    gelöst und mit     loJ    Teilen     konz.     Salzsäure versetzt. Unterhalb<B>50</B> wird eine  konzentrierte, wässerige Lösung von 3,6 Tei  len     Natriumnitrit        zugetropft.    Beim Verdün  nen mit Wasser erhält man eine gelbe, klare  Lösung der     Diazoniumverbindung.     



  Der Lösung von 18 Teilen des     Dinatrium-          salzes    der     ?-Oxynaphthalin-6,8-disulfonsäure     in 500 Teilen Wasser werden     noeh    1.20 Teile       wasserfreies        Natriumearbonat    zugesetzt. Obige       Diazoniunilösun    - wird bei<B>00</B> langsam einge  tragen. Die     Farbstoffbildung    ist     naeh    einigen  Stunden beendigt. Der Farbstoff wird abge  saugt, mit verdünnter     Natriumehloridlösung     gewaschen und hierauf getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized -I'-tertiary amy1-4-chloro-2-aminodiphenyl ether is combined with '? -Oxynaplithalin-6,8-disulphonic acid.



  The new dye forms an orange powder that dissolves in water with an orange color and dyes wool from an acetic acid bath in orange tones.



  The 4'-tertiaryamyl-4-chloro-2-aminodililienylether used as the starting material in the present process can be used by a known method by condensation of 4-tertiaryamyl-1-oxybenzene with 1,4-dichloro-2-nitrobenzene and the following Reduction of the nitro group of the 4'-tertiaryamyl-4-- chloro-2-nitrodiphenyl ether obtained to the amino group.



  The diazotization can also be carried out by known methods customary for amines which are difficult to diazotize, for example in the presence of alcohol or acetic acid or with the aid of nitrosylsulfuric acid.



  The coupling takes place with, advantageously in an alkaline, preferably alkaline alkali carbonate medium, if desired with the use of suitable additives that promote the coupling reaction, such as alcohol, pyridine, etc.

      <I> Example: </I> 11-, 5 parts of 4'-tertiary amyl-1-chloro-2-amino-diplienylätlier are dissolved in 50 parts of 100% acetic acid and mixed with 10J parts of conc. Hydrochloric acid added. Below <B> 50 </B> a concentrated, aqueous solution of 3.6 parts of sodium nitrite is added dropwise. When diluting with water, a yellow, clear solution of the diazonium compound is obtained.



  1.20 parts of anhydrous sodium carbonate are added to the solution of 18 parts of the disodium salt of? -Oxynaphthalene-6,8-disulfonic acid in 500 parts of water. The above Diazoniunilösun - is slowly entered at <B> 00 </B>. The dye formation is complete after a few hours. The dye is filtered off with suction, washed with dilute sodium chloride solution and then dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- azotierten 4-'-Tertiä.ramyl-4-chlor-2-aminodi- phenylätlier mit 2-Oxynaphthalin-6,8-disul- fonsäure vereinigt. Der neue Farbstoff bildet ein oranges Pul ver, das sich in Wasser mit oranger Farbe löst und Wolle aus essigsaurem Bade in oran gen Tönen färbt. Claim: Process for the production of an azo dye, characterized in that diazotized 4 -'-tertiary ramyl-4-chloro-2-aminodiphenyl ethers are combined with 2-oxynaphthalene-6,8-disulfonic acid. The new dye forms an orange powder that dissolves in water with an orange color and dyes wool from an acetic acid bath in orange tones.
CH270538D 1948-02-26 1947-04-30 Process for the preparation of an azo dye. CH270538A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH270538A true CH270538A (en) 1950-09-15

Family

ID=4477791

Family Applications (1)

Application Number Title Priority Date Filing Date
CH270538D CH270538A (en) 1948-02-26 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH270538A (en)

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