CH272480A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272480A
CH272480A CH272480DA CH272480A CH 272480 A CH272480 A CH 272480A CH 272480D A CH272480D A CH 272480DA CH 272480 A CH272480 A CH 272480A
Authority
CH
Switzerland
Prior art keywords
azo dye
yellow
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 CH272480A publication Critical patent/CH272480A/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)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotierten    4'-     Tertiäramyl    - 2 -     aminodiphe-          nyläther    mit     1-(2'-Chlor-5'-sulfo)-phenyl-3-          methyl-5-pyrazolon    vereinigt.  



  Der neue Farbstoff bildet ein gelbes Pul  ver, das sich in Wasser mit gelber Farbe  löst und     Wolle    aus essigsaurem Bade in  grüngelben Tönen färbt.  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-2-amino-          diphenyläther    kann nach an sich bekannter  Methode durch Kondensation von     4-Tertiär-          amyl-l-oxybenzol    mit     1-Chlor-2-nitrobenzol     und nachfolgende Reduktion der Nitro  gruppe des erhaltenen     4'-Tertiäramyl-2-ni-          trodiphenyläthers    zur     Aminogruppe    herge  stellt werden.  



  Die     Diazotierung    kann wie üblich z. B.  mit Salzsäure und     Natriumnitrit    durchge  führt werden.  



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



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiäramyl-2-amino-1,1'-di-          phenyläther    werden mit 46 Teilen konzen  trierter Salzsäure verrieben. Nach einer    Stunde wird die Suspension des     Chlorhy-          drates    mit 120 Teilen einer gesättigten Na  triumchloridlösung     angeschlämmt    und hier  auf unterhalb     +    5   allmählich mit einer  konzentrierten     wässerigen    Lösung von 7,2  Teilen     Natriumnitrit    versetzt.

   Die schwach  gelb gefärbte     Diazolösung        wird    bei 0  mit  der Lösung von 31 Teilen des     Natriumsalzes     des     1-(2'-Chlor-5'-sulfo)-phenyl-3-methyl-5-          pyrazolons    in 330 Teilen einer gesättigten       Natriumcarbonatlösung    vermischt. Der so  fort entstehende gelbe Farbstoff wird nach  einigen Stunden     abfiltriert    und in heissem  Wasser gelöst. Die Lösung wird von allfälli  gen geringen Verunreinigungen     abfiltriert     und mit so viel     Natriumehlorid    versetzt, dass  die Hauptmenge des Farbstoffes gefällt  wird.

   Der Farbstoff wird     abfiltriert    und ge  trocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized 4'-tertiaryamyl-2-aminodiphenyl ether is combined with 1- (2'-chloro-5'-sulfo) -phenyl-3-methyl-5-pyrazolone .



  The new dye forms a yellow powder that dissolves in water with a yellow color and dyes wool from an acetic acid bath in green-yellow shades.



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



  The diazotization can, as usual, for. B. with hydrochloric acid and sodium nitrite Runaway leads.



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



  <I> Example: </I> 25.5 parts of 4'-tertiaryamyl-2-amino-1,1'-diphenyl ether are triturated with 46 parts of concentrated hydrochloric acid. After one hour, the suspension of the chlorohydrate is slurried with 120 parts of a saturated sodium chloride solution and a concentrated aqueous solution of 7.2 parts of sodium nitrite is gradually added here to below +5.

   The pale yellow colored diazo solution is mixed at 0 with the solution of 31 parts of the sodium salt of 1- (2'-chloro-5'-sulfo) -phenyl-3-methyl-5-pyrazolone in 330 parts of a saturated sodium carbonate solution. 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.

   The dye is filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man diazotierten 4'-Tertiäramyl-2-amino-diphe- nyläther mit 1-(2'-Chlor-5'-sulfo)-phenyl-3- methyl-5-pyrazolon vereinigt. Der neue Farbstoff bildet ein gelbes Pul ver, das sich in Wasser mit gelber Farbe löst und Wolle aus essigsaurem Bade in grüngel ben Tönen färbt. Claim: Process for the production of an azo dye, characterized in that diazotized 4'-tertiaryamyl-2-amino-diphenyl ether with 1- (2'-chloro-5'-sulfo) -phenyl-3-methyl-5 -pyrazolone combined. The new dye forms a yellow powder that dissolves in water with a yellow color and dyes wool from acetic acid bath in green-yellow shades.
CH272480D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272480A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272480T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272480A true CH272480A (en) 1950-12-15

Family

ID=25731191

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272480D CH272480A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272480A (en)

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