CH272492A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

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Publication number
CH272492A
CH272492A CH272492DA CH272492A CH 272492 A CH272492 A CH 272492A CH 272492D A CH272492D A CH 272492DA CH 272492 A CH272492 A CH 272492A
Authority
CH
Switzerland
Prior art keywords
blue
preparation
azo dye
red
parts
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 CH272492A publication Critical patent/CH272492A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbatoffes.       Es     wurde    gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  dianotierten     4'-Tertiäramyl-2-aniinodiphenyl-          äther    mit     1-Ben7oylamino-8-oxyiiaphthalin-          4,6-disulfonsäure    vereinigt.  



       Der    neue Farbstoff bildet ein blaurotes  Pulver, das sieh in siedendem Wasser mit  blauroter Farbe löst und Wolle aus essigsau  rem Bade in echten blauroten Tönen färbt.  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäram#1-2-amino-          diiihenyläther    kann nach an sich bekannter       Methode    durch Kondensation von     4-Tertiär-          ainyl-l-oxybenzol    mit     1-Chlor-2-nitrobenzol     und nachfolgende     Reduktion    der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-2-nitrodiphenyl-          ä        Hiers    zur     Aininogruppe    hergestellt werden.  



  Die Dianotierung kann wie üblich, z. B. mit       Salzsäure    und     Natriiininitrit,        durchgeführt     werden.  



  Die Kupplung erfolgt. mit. Vorteil in alka  lischem, vorzugsweise     alka.liearbonatalkali-          seliem        Medium.     



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiäraniyl-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     -esättigten        Natriilmchloridlösung        ange-          schlämmt        lind    hierauf unterhalb +     50    all  i     m        ählieh        mit        einer        konzentrierten        

  wässericen        c          Lösung-    von 7,2 Teilen     Natriuinnitrit    versetzt.  Die     sehyvaeh    gelb gefärbte     Diazolösiuig    wird  bei 00 mit der Lösung von 47 Teilen des     Di-          natriumsalzes    der     1-Benzoylamin.o-8-oxynaph-          thalin-4,6-disulfonsäure    in 330 Teilen einer  gesättigten     Natriumearbonatlösung    vermischt.  Der entstehende Farbstoff wird     abfiltriert     und hierauf aus heissem Nasser umkristalli  siert und getrocknet.



  Process for the production of an azo carbate. It has been found that a valuable azo dye is obtained if dianotated 4'-tertiaryamyl-2-aniinodiphenyl ether is combined with 1-benzoylamino-8-oxyiiaphthalene-4,6-disulfonic acid.



       The new dye forms a blue-red powder that dissolves in boiling water with a blue-red color and dyes wool from an acetic acid bath in real blue-red shades.



  The starting material used in the present process 4'-Tertiäram # 1-2-amino-diiihenyläther can by condensation of 4-Tertiär- ainyl-l-oxybenzene with 1-chloro-2-nitrobenzene and subsequent reduction of the Nitro group of the 4'-tertiaryamyl-2-nitrodiphenyl- ä obtained here to the amino group.



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



  The coupling takes place. With. Advantage in alkaline, preferably alkaline carbonate alkaline medium.



  <I> Example: </I> 25.5 parts of 4'-tertiary aniyl-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 +50 every few times with a concentrated solution

  aqueous solution of 7.2 parts of sodium nitrite added. The sehyvaeh yellow colored diazo solution is mixed at 00 with the solution of 47 parts of the disodium salt of 1-benzoylamin.o-8-oxynaphthalene-4,6-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)

PATTNTANSPRUCII Verfahren zur Heisstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass nian dianotierten 4'-Tertiäramyl-2-aminodiphenyl- ätlier mit l.-Benzoylamino-8-oxyiia.phthalin- 4.6-disulfonsä.ttre vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das sich in siedendem Wasser mit blauroter Farbe löst und Wolle ans essigsau rem Bade in echten blauroten Tönen färbt. PATTNTANSPRUCII Process for the preparation of an azo dye, characterized in that dianotated 4'-tertiaryamyl-2-aminodiphenyl ether is combined with 1.-benzoylamino-8-oxyiia.phthalin-4,6-disulphonic acid. The new dye forms a blue-red powder that dissolves in boiling water with a blue-red color and dyes wool in real blue-red tones when used in an acetic bath.
CH272492D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272492A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272492T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272492A true CH272492A (en) 1950-12-15

Family

ID=25731203

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272492D CH272492A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272492A (en)

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