CH249779A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH249779A
CH249779A CH249779DA CH249779A CH 249779 A CH249779 A CH 249779A CH 249779D A CH249779D A CH 249779DA CH 249779 A CH249779 A CH 249779A
Authority
CH
Switzerland
Prior art keywords
dye
azo dye
preparation
parts
sulfonic acid
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 CH249779A publication Critical patent/CH249779A/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
    • C09B29/34—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
    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
    • C09B31/053—Amino naphthalenes
    • C09B31/057—Amino naphthalenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof

Landscapes

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

Description

  

      Zusatzpatent    zum Hauptpatent Nr. 244603.    Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  neuen     Azofarbs        toff    gelangt, wenn man den       diazo@tierten        Monoazofarbstoff    der Formel  
EMI0001.0007     
    mit 1- N -     Phenyl    - (4'-     phenoxy)    -     a.minonaph-          thalin-8-s.ulfon:säure    kuppelt.  



  Der neue Farbstoff bildet ein dunkel  blaues Pulver, das, Wolle aus     schwach    saurem  Bade in echten, rein blauen Tönen färbt.         Beispiel:     35     Teile    1-     Aminobenzol    - 3 -     sulfonsäure     werden wie üblich     diazotiert    und in     mineral-          saurer    Lösung mit 29 Teilen     1-Amino-naph          thalin        gekuppelt.    Da     Natriumsalz    des gebil  deten     Azofarbstoffes    wird in     wässeriger    Lö  sung mit der berechneten Menge 

  Natrium  nitrit versetzt und bei 30-35  C in über  schüssige verdünnte Salzsäure gegossen. Die  in     orangen    Flocken     ausfallende        Diazonium-          verbindung    wird nach einiger Zeit     abfiltnert,     bei 0  C mit 120 Teilen Methylalkohol ver  rieben und hierauf mit einer eiskalten Lö  sung von 80 Teilen 1-N-Phenyl-(4'-phenoxy)-         aminonaphthalin-8-sulfo#nsäure    in 800 Teilen  Methylalkohol allmählich     vermischt.    Zur Ver  vollständigung der Kupplung     wird    noch       einige    Stunden bei 0  C verrührt, worauf man  den     Farbstoff,

      der getrocknet ein dunkles  Pulver darstellt,     abfiltriert.    Das in dieser  Form     in,    Wasser fast unlösliche Produkt löst  sich bei Zusatz von     Natriumhydroxyd    glatt  mit tiefblauer Farbe. Aus dieser Lösung     wird     das     Natrium@salz    der     Farbstoffsulfonsäure     durch     Natriumchlorid    gefällt. Es ergibt auf  Wolle .aus schwach saurem Bade gefärbt ein  sehr echtes und reines Blau.



      Additional patent to main patent No. 244603. Process for the production of an azo dye. It has been found that a new azo dye is obtained if one uses the diazo @ tated monoazo dye of the formula
EMI0001.0007
    with 1- N - phenyl - (4'-phenoxy) - a.minonaphthalin-8-s.ulfonic acid: acid coupling.



  The new dye forms a dark blue powder that dyes wool from a weakly acidic bath in real, pure blue tones. Example: 35 parts of 1-aminobenzene-3-sulfonic acid are diazotized as usual and coupled with 29 parts of 1-aminonaphthalene in a mineral acid solution. The sodium salt of the azo dye formed is dissolved in aqueous solution with the calculated amount

  Sodium nitrite was added and poured into excess dilute hydrochloric acid at 30-35 C. The diazonium compound, which precipitates out in orange flakes, is filtered off after a while, rubbed with 120 parts of methyl alcohol at 0 C and then treated with an ice-cold solution of 80 parts of 1-N-phenyl- (4'-phenoxy) -aminonaphthalene-8- sulfonic acid gradually mixed in 800 parts of methyl alcohol. To complete the coupling is stirred for a few hours at 0 C, whereupon the dye,

      which when dried represents a dark powder, filtered off. The product, which is almost insoluble in water in this form, dissolves smoothly with a deep blue color when sodium hydroxide is added. The sodium salt of the dye sulfonic acid is precipitated from this solution using sodium chloride. On wool, dyed from a weakly acidic bath, it gives a very genuine and pure blue.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herste=llung eines Azofarb- stoffes, dadurch gekennzeichnet, dass der diazotierte Monoazofarbstoff der Formel EMI0001.0048 mit 1-N-Phenyl - (4' -phenoxy) - aminonaph- thalin-8-sulfonsäure gekuppelt wird. Der neue Farbstoff bildet ein dunkel blaues Pulver, das Wolle aus schwach saurem Bade in echten, rein blauen Tönen färbt. PATENT CLAIM: Process for the production of an azo dye, characterized in that the diazotized monoazo dye of the formula EMI0001.0048 with 1-N-phenyl - (4'-phenoxy) - aminonaphthalene-8-sulfonic acid is coupled. The new dye forms a dark blue powder that dyes wool from a weakly acidic bath in real, pure blue tones.
CH249779D 1945-07-12 1945-07-12 Process for the preparation of an azo dye. CH249779A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249779T 1945-07-12
CH244603T 1946-06-07

Publications (1)

Publication Number Publication Date
CH249779A true CH249779A (en) 1947-07-15

Family

ID=25728965

Family Applications (1)

Application Number Title Priority Date Filing Date
CH249779D CH249779A (en) 1945-07-12 1945-07-12 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH249779A (en)

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