CH272490A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272490A
CH272490A CH272490DA CH272490A CH 272490 A CH272490 A CH 272490A CH 272490D A CH272490D A CH 272490DA CH 272490 A CH272490 A CH 272490A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
parts
dye
tertiary
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 CH272490A publication Critical patent/CH272490A/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
    • C09B29/24—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

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     Azofarbatoffes.       Es wurde gefunden, dass man zu     einem     wertvollen     Azofarbstoff    gelangt, wenn man  dianotierten     4'-Tertiäramyl-2-aminocliphenyl-          äther    mit     2-Oxvnaphtlialin-3,6-disttlfonsäure     vereinigt.  



  Der neue     Farbstoff    bildet ein rotes Pul  ver, das sich in Wasser mit roter Farbe löst  und Wolle aus     essigsaurem    Bade in reinen  und echten scharlachroten Tönen färbt.  



  Der beim vorliegenden Verfahren als Ans  gangsstoff dienende     4'-Tei-tiäranivl-2-aniino-          diphenyläther        kann    nach an sieh bekannter  Methode dureh Kondensation von     4-Tertiär-          amyl-l-oxybenzol    mit     1-Clilor-2-nitrobenzol     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tei-tiäraniyl-2-nitrodiphenyl-          äthers    zur     Aminogruppe    hergestellt. werden.  



  Die Dianotierung kann wie üblich, z. B. mit  Salzsäure und     Natriumnitrit,        durelio-efiihi-t     werden.  



  Die Kupplung erfolgt mit Vorteil in     al-          kaliseheni,    vorzugsweise     alkaliearbonatalkali-          sehem    Medium.    <I>Beispiel:</I>  25,5 Teile     4'-Tertiäi-amyl-2-amino-1.,1'-di-          phenyläther    werden mit 46 Teilen     konz.    Salz-         säure    verrieben.

   Nach einer     Stunde    wird die  Suspension des Chlorhydrates mit 120 Teilen  einer gesättigten     Natriumchloridlösung        ange-          schlämmt.    und hierauf unterhalb     +        56        allmä.h-          lieh    mit einer     konzentriertenwässerigenLösung     von 7,2 Teilen     Natriumnitrit    versetzt.

   Die       seliwaeli    gelb gefärbte     Diazolösung    wird bei  00 mit der Lösung von 35 Teilen des     Di-          natriumsalzes    der     2-Oxynaphthalin-3,6-disul-          fonsHure    in 330 Teilen einer     gesättigten        Na-          triuinearbonatlösung    vermischt. Der entste  llende Farbstoff wird     abfiltriert    und hierauf  aus heissem Wasser umkristallisiert und ge  trocknet.



  Process for the production of an azo carbate. It has been found that a valuable azo dye is obtained if dianotated 4'-tertiaryamyl-2-aminocliphenyl ether is combined with 2-oxynaphthalene-3,6-distalphonic acid.



  The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acetic acid bath in pure and genuine scarlet shades.



  The 4'-Tei-tiäranivl-2-aniino-diphenyl ether serving as the starting material in the present process can, according to a method known per se, by condensation of 4-tertiary amyl-l-oxybenzene with 1-Clilor-2-nitrobenzene and subsequent reduction of the Nitro group of the 4'-Tei-tiäraniyl-2-nitrodiphenyl ether obtained to the amino group. will.



  The dianotation can be carried out as usual, e.g. B. with hydrochloric acid and sodium nitrite, durelio-efiihi-t.



  The coupling is advantageously carried out in an alkali metal, preferably alkali carbonate alkaline medium. <I> Example: </I> 25.5 parts of 4'-tertiary-amyl-2-amino-1., 1'-diphenyl ether are concentrated with 46 parts. Hydrochloric acid triturated.

   After one hour, the suspension of the chlorohydrate is slurried with 120 parts of a saturated sodium chloride solution. and then below +56 gradually borrowed a concentrated aqueous solution of 7.2 parts of sodium nitrite.

   The seliwaeli yellow colored diazo solution is mixed at 00 with the solution of 35 parts of the disodium salt of 2-oxynaphthalene-3,6-disulphonic acid in 330 parts of a saturated sodium carbonate solution. The resulting dye is filtered off and then recrystallized from hot water and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man dianotierten 4'-Tertiäram.yl-2-aminodiphen.#-1- äther mit. 2-Oxvnaplithalin-3,6-disulfonsäure vereinigt.. Der neue Farbstoff bildet ein rotes Pulver, das sieh in Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade in reinen und echten scharlachroten Tönen färbt. PATENT CLAIM: Process for the production of an azo dye, characterized in that dianotated 4'-tertiary am.yl-2-aminodiphen. 2-Oxvnaplithalin-3,6-disulfonic acid combined .. The new dye forms a red powder which dissolves in water with a red color and dyes wool from acetic acid bath in pure and genuine scarlet shades.
CH272490D 1948-02-26 1950-03-23 Process for the preparation of an azo dye. CH272490A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH270538T 1948-02-26
CH272490T 1950-03-23

Publications (1)

Publication Number Publication Date
CH272490A true CH272490A (en) 1950-12-15

Family

ID=25731201

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272490D CH272490A (en) 1948-02-26 1950-03-23 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272490A (en)

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