CH268076A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH268076A
CH268076A CH268076DA CH268076A CH 268076 A CH268076 A CH 268076A CH 268076D A CH268076D A CH 268076DA CH 268076 A CH268076 A CH 268076A
Authority
CH
Switzerland
Prior art keywords
azo dye
parts
preparation
red
benzyloxy
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 CH268076A publication Critical patent/CH268076A/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
    • C09B29/10—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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man     di-          azotiertes        2-Amino-l-benzyloxy-4-tertiäramyl-          benzol    mit     1-Oxynaplithalin-3,6-disulfonsäure     vereinigt.  



  Der neue Farbstoff bildet ein rotes Pulver,  das sieh in Wasser mit roter Farbe löst und        'olle    aus saurem Bade in roten Tönen färbt.  



  Das beim vorliegenden Verfahren als Aus  gangsstoff dienende     2-Amino-l-benzyloxy-4-          tertiäi-amylbenzol    lässt, sich beispielsweise her  stellen durch     Nitrierung    von     1-Oxy-4-tertiär-          amylbenzol,        Benzylierung    der     Hydroxyl-          gi-uppe    und Reduktion des     Nitroäthers.     



  Die     Diazotierung    kann nach bekannten,  für schwer     diazotierbare    Amine üblichen.     Me-          tlioden,    beispielsweise in Gegenwart von Alko  hol oder Essigsäure,     durchgeführt    werden.  



  Die Kupplung erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkaliearbonatalkali-          sehem    Medium.  



  <I>Beispiel:</I>  8,1 Teile     2-Amino-l-benzyloxy-4-tertiär-          amylbenzol    werden in 65 Teilen heissem Äthyl-         alkohol    gelöst und unterhalb 300 mit 11 Teilen  konzentrierter Salzsäure versetzt. Diese alko  holische Lösung des Chlorhydrates wird unter  halb     10     durch Zugabe einer gesättigten wäs  serigen Lösung von 2,1 Teilen     Natriumnitrit          diazotiert.     



  Der Lösung von 11 Teilen des     Dinatrium-          salzes    der     1-Oxynaphthalin-3,6-clisulfonsäure     in 150 Teilen Wasser werden noch 10 Teile  wasserfreies     Natriumcarbonat    zugesetzt. Dann  wird obige     Diazolösung    bei 00 eingetragen.       Naeli    einigen Stunden wird der rote Farbstoff       abfiltriert    und getrocknet. .



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized 2-amino-1-benzyloxy-4-tertiaryamylbenzene is combined with 1-oxynaplithalin-3,6-disulfonic acid.



  The new dye forms a red powder, which dissolves in water with a red color and colors oil from an acid bath in red tones.



  The 2-amino-1-benzyloxy-4-tertiary-amylbenzene used as starting material in the present process can be produced, for example, by nitration of 1-oxy-4-tertiary amylbenzene, benzylation of the hydroxyl gi-uppe and reduction of the Nitro ethers.



  Diazotization can be carried out according to known amines which are customary for amines which are difficult to diazotize. Metliodes, for example in the presence of alcohol or acetic acid, are carried out.



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



  <I> Example: </I> 8.1 parts of 2-amino-1-benzyloxy-4-tertiary amylbenzene are dissolved in 65 parts of hot ethyl alcohol and 11 parts of concentrated hydrochloric acid are added below 300 parts. This alcoholic solution of the chlorohydrate is diazotized below half past ten by adding a saturated aqueous solution of 2.1 parts of sodium nitrite.



  10 parts of anhydrous sodium carbonate are added to the solution of 11 parts of the disodium salt of 1-oxynaphthalene-3,6-clisulfonic acid in 150 parts of water. Then the above diazo solution is entered at 00. After a few hours, the red dye is filtered off and dried. .

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- azotiertes 2-Amino-l-benzyloxy-4-tertiäramyl- benzol mit. 1-Oxynaphtlialin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pul ver, das sich in Wasser mit roter Farbe löst und Wolle aus saurem Bade in roten Tönen färbt. PATENT CLAIM: Process for the production of an azo dye, characterized in that diazotized 2-amino-1-benzyloxy-4-tertiaryamylbenzene is used. 1-oxynaphthalene-3,6-disulfonic acid combined. The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acid bath in red shades.
CH268076D 1947-04-30 1947-04-30 Process for the preparation of an azo dye. CH268076A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH268076T 1947-04-30
CH262279T 1947-04-30

Publications (1)

Publication Number Publication Date
CH268076A true CH268076A (en) 1950-04-30

Family

ID=25730564

Family Applications (1)

Application Number Title Priority Date Filing Date
CH268076D CH268076A (en) 1947-04-30 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH268076A (en)

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