CH244603A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH244603A
CH244603A CH244603DA CH244603A CH 244603 A CH244603 A CH 244603A CH 244603D A CH244603D A CH 244603DA CH 244603 A CH244603 A CH 244603A
Authority
CH
Switzerland
Prior art keywords
amino
azo dye
preparation
acid
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 CH244603A publication Critical patent/CH244603A/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
    • C09B29/34—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  neuen wertvollen     Azofarbstoff    gelangt, wenn  man die     Diazoniumverbindung    der     1-Amino-          8-oxynaphthalin-3,6-disulfonsäure    mit einer  solchen     1-Amino        -naphthalin    - 8 -     sulf        onsäure     vereinigt, die in der     Aminogruppe    durch  einen     Diarylätherrest    substituiert ist.

   Das  neue Verfahren ist also dadurch gekennzeich  net, dass     diazotierte        1-Amino-8-oxynaphtha-          lin-3,6-disulfonsäure    mit     1-N-Phenyl-(4'-          phenoxy)-aminonaphthalin-8-sulfonsäure    ge  kuppelt wird.  



  Der neue Farbstoff bildet     ein    dunkel  blaues Pulver, das aus essigsaurem Bade auf  Wolle gefärbt ein echtes, reines Blau ergibt.  <I>Beispiel:</I>  Die wie üblich dargestellte     Diazonium-          verbindung    aus 319 Teilen     1-Amino-8-oxy-          naphthalin-3,6-disulfonsäure    wird bei 0  C  mit der Lösung von 400 Teilen     1-N-Phenyl-          (4'-phenoxy)        -aminonaphtha.lin-8-sulfonsäure     in 4000 Teilen Methylalkohol vermischt.

   Man  verrührt die tiefblau erscheinende Suspen  sion, bis keine     Diazoniumverbindung    mehr  nachgewiesen werden kann, und isoliert den  Farbstoff durch Zugabe von wässeriger Na  triumchloridlösung. Zur Reinigung wird er    in     verdünnter        Natriumcarbonatlösung    gelöst  und mit Kochsalzlösung wieder gefällt. Er  stellt     getrocknet    ein dunkelblaues Pulver dar  und ergibt aus essigsaurem Bade auf Wolle  gefärbt ein echtes, reines Blau.  



  Die 1- N -     Phenyl    -     (4'-        phenoxy)    -     amino-          naphthaa-8-sulfonsäure    wird erhalten, in  dem man     1-Aminonaphthalin-8-sulfonsäure     20 Stunden bei 180  C mit einem Überschuss  an 4 -     Amino    -1,1' -     diphenyläther    verrührt.  Nach Entfernung des überschüssigen     Diaryl-          äthers,    z. B. durch     Vakuumdestillation,    lässt  sich die neue Säure dank ihrer überraschen  den Löslichkeit, z. B. in Benzol, mit Hilfe  von organischen     Lösungsmitteln    reinigen.



  Process for the production of an azo dye. It has been found that a new, valuable azo dye is obtained if the diazonium compound of 1-amino-8-oxynaphthalene-3,6-disulfonic acid is combined with such a 1-amino-naphthalene-8-sulfonic acid which is in the amino group is substituted by a diaryl ether radical.

   The new process is thus characterized in that diazotized 1-amino-8-oxynaphthalene-3,6-disulfonic acid is coupled with 1-N-phenyl- (4'-phenoxy) -aminonaphthalene-8-sulfonic acid.



  The new dye forms a dark blue powder which, when dyed with an acetic acid bath on wool, turns into a real, pure blue. <I> Example: </I> The diazonium compound prepared as usual from 319 parts of 1-amino-8-oxynaphthalene-3,6-disulfonic acid is mixed with a solution of 400 parts of 1-N-phenyl- (4'-phenoxy) -aminonaphtha.lin-8-sulfonic acid mixed in 4000 parts of methyl alcohol.

   The suspension, which appears deep blue, is stirred until no more diazonium compound can be detected, and the dye is isolated by adding aqueous sodium chloride solution. To clean it, it is dissolved in dilute sodium carbonate solution and reprecipitated with saline solution. When dried, it represents a dark blue powder and, when dyed on wool in an acetic acid bath, produces a real, pure blue.



  The 1-N-phenyl- (4'-phenoxy) -amino-naphthaa-8-sulfonic acid is obtained by adding 1-aminonaphthalene-8-sulfonic acid for 20 hours at 180.degree. C. with an excess of 4-amino-1.1 '- diphenyl ether stirred. After removing the excess diaryl ether, z. B. by vacuum distillation, the new acid can surprise thanks to its solubility, z. B. in benzene, clean with the help of organic solvents.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azo- farbstoffes, dadurch gekennzeichnet, dass di- azotierte 1-Amino-8-oxynaphthalin-3,6-disul- fonsäure mit 1-N-Phenyl-(4'-phenoxy)-amino- naphthalin-8-sulfonsäure gekuppelt wird. Der neue Farbstoff bildet ein dunkel blaues Pulver, das aus essigsaurem Bade auf Wolle gefärbt ein echtes, reines Blau ergibt. PATENT CLAIM: Process for the production of an azo dye, characterized in that diacotized 1-amino-8-oxynaphthalene-3,6-disulfonic acid with 1-N-phenyl- (4'-phenoxy) -amino-naphthalene- 8-sulfonic acid is coupled. The new dye forms a dark blue powder which, when dyed with an acetic acid bath on wool, turns into a real, pure blue.
CH244603D 1946-06-07 1945-07-12 Process for the preparation of an azo dye. CH244603A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH244603T 1946-06-07

Publications (1)

Publication Number Publication Date
CH244603A true CH244603A (en) 1946-09-30

Family

ID=4464373

Family Applications (1)

Application Number Title Priority Date Filing Date
CH244603D CH244603A (en) 1946-06-07 1945-07-12 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH244603A (en)

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