CH272488A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272488A
CH272488A CH272488DA CH272488A CH 272488 A CH272488 A CH 272488A CH 272488D A CH272488D A CH 272488DA CH 272488 A CH272488 A CH 272488A
Authority
CH
Switzerland
Prior art keywords
yellow
azo dye
preparation
dye
tertiaryamyl
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 CH272488A publication Critical patent/CH272488A/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-aminodiphenyl-          äther    mit     l.-(2',5'-Dielilor-4'-sulfo)-phenyl-3-          methyl-5-py        razolon    vereinigt.  



  Der neue Farbstoff bildet ein gelbes Pul  ver, das sieh in Wasser mit gelber Farbe löst  und     -trolle    aus essigsaurem Bade in grüngel  ben Tönen färbt.  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-2-amino-          diphenyläther    kann nach an sieh bekannter  Methode durch Kondensation von     4-Tertiär-          am        yl-l-oxybenzol    mit     1-Chlor-2-nitrobenzol.     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-2-nitrodiphenyl-          äthers    zur     Aminogruppe    hergestellt werden.  



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



  Die Kupplung erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkalicarbonatalkali-          schem    Medium.  



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiäramyl-2-aniino-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     Natriumehloridlösung        ange-          sehlämmt    und hierauf unterhalb + 50 all  mählich mit einer konzentrierten wässerigen  Lösung von 7,2 Teilen     Natriumnitrit    versetzt.

    Die sehwach gelb gefärbte     Diazolösimg    wird  bei 00 mit der Lösung von 35 Teilen des Na  triumsalzes des     1-(2',5'-Diehlor-4'-siilfo)-phe-          n%#1-3-methyl-5-pyrazolons    in 330 Teilen einer       ;esättigten        Natriumcarbonatlösung    vermischt.  Der sofort, entstehende gelbe Farbstoff wird  nach einigen Stunden     abfiltriert    und in hei  ssem Wasser gelöst. Die Lösung wird von  allfälligen geringen Verunreinigungen     abfil-          triert    und mit so viel     Natriumehlorid    versetzt,  dass die Hauptmenge des Farbstoffes gefällt.  wird.

   Der Farbstoff wird     abfiltriert    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-aminodiphenyl ether with l .- (2 ', 5'-Dielilor-4'-sulfo) -phenyl-3-methyl- 5-py razolone combined.



  The new dye forms a yellow powder that dissolves in water with a yellow color and colors rolls of acetic acid bath in green-yellow shades.



  The 4'-tertiaryamyl-2-aminodiphenyl ether used as starting material in the present process can be prepared by condensation of 4-tertiary-amyl-1-oxybenzene with 1-chloro-2-nitrobenzene according to a method known per se. and subsequent reduction of the nitro group of the 4'-tertiaryamyl-2-nitrodiphenyl ether obtained to the amino group.



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



  The coupling is advantageously carried out in an alkaline, preferably alkaline carbonate-alkaline medium.



  <I> Example: </I> 25.5 parts of 4'-tertiaryamyl-2-aniino-1,1'-diphenyl ether are concentrated with 46 parts. Triturated with hydrochloric acid. After one hour, the suspension of the chlorohydrate is lamed with 120 parts of a saturated sodium chloride solution, and a concentrated aqueous solution of 7.2 parts of sodium nitrite is then gradually added below + 50.

    The weak yellow colored Diazolösimg is at 00 with the solution of 35 parts of the sodium salt of 1- (2 ', 5'-Diehlor-4'-siilfo) -phe- n% # 1-3-methyl-5-pyrazolons in 330 parts of a saturated sodium carbonate solution mixed. The yellow dye which forms immediately is filtered off after a few hours and dissolved in hot water. Any minor impurities are filtered off from the solution and so much sodium chloride is added that most of the dye is precipitated. becomes.

   The dye is filtered off and dried.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, da.ss man diazotierten 4'-Tertiäramyl-2-aminodiphenyl- äther mit 1-(2',5'-Dichlor-4'-sulfo)-phenyl-3- methyl-5-pyrazolon vereinigt. Der neue Farbstoff bildet ein gelbes Pul ver, das sich in -Wasser mit gelber Farbe löst und -Volle aus essigsaurem Bade in grüngel ben Tönen färbt. PATENT CLAIM Process for the production of an azo dye, characterized in that diazotized 4'-tertiaryamyl-2-aminodiphenyl ether with 1- (2 ', 5'-dichloro-4'-sulfo) -phenyl-3-methyl -5-pyrazolone combined. The new dye forms a yellow powder, which dissolves in water with a yellow color and colors full in acetic acid bath in green-yellow shades.
CH272488D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272488A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272488T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272488A true CH272488A (en) 1950-12-15

Family

ID=25731199

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272488D CH272488A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272488A (en)

Similar Documents

Publication Publication Date Title
CH272488A (en) Process for the preparation of an azo dye.
CH272485A (en) Process for the preparation of an azo dye.
CH272484A (en) Process for the preparation of an azo dye.
CH272482A (en) Process for the preparation of an azo dye.
CH272480A (en) Process for the preparation of an azo dye.
CH272492A (en) Process for the preparation of an azo dye.
CH272486A (en) Process for the preparation of an azo dye.
CH211819A (en) Process for the preparation of an azo dye.
CH272491A (en) Process for the preparation of an azo dye.
CH272483A (en) Process for the preparation of an azo dye.
CH272487A (en) Process for the preparation of an azo dye.
CH272490A (en) Process for the preparation of an azo dye.
CH272493A (en) Process for the preparation of an azo dye.
CH211825A (en) Process for the preparation of an azo dye.
CH272494A (en) Process for the preparation of an azo dye.
CH211821A (en) Process for the preparation of an azo dye.
CH211822A (en) Process for the preparation of an azo dye.
CH199369A (en) Process for the preparation of an azo dye.
CH211804A (en) Process for the preparation of an azo dye.
CH211833A (en) Process for the preparation of an azo dye.
CH211828A (en) Process for the preparation of an azo dye.
CH211827A (en) Process for the preparation of an azo dye.
CH211815A (en) Process for the preparation of an azo dye.
CH199370A (en) Process for the preparation of an azo dye.
CH211803A (en) Process for the preparation of an azo dye.