CH309776A - Process for the preparation of a monoazo dye. - Google Patents

Process for the preparation of a monoazo dye.

Info

Publication number
CH309776A
CH309776A CH309776DA CH309776A CH 309776 A CH309776 A CH 309776A CH 309776D A CH309776D A CH 309776DA CH 309776 A CH309776 A CH 309776A
Authority
CH
Switzerland
Prior art keywords
blue
amino
dye
red
preparation
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 CH309776A publication Critical patent/CH309776A/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
    • C09B29/02—Monoazo dyes prepared by diazotising and coupling from diazotised o-amino-hydroxy compounds
    • 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

Landscapes

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

Description

  

  <B>Verfahren zur Herstellung eines</B>     Monoazofarbsto$es.       Es wurde gefunden,     da.ss    man zu einem  wertvollen     Monoazofarbstoff    gelangt, wenn  man     diazotiertes        2-Amino-l-methoxy-4-tertiär-          amylbenzol    mit 1-     (4'-        Tertiärbutylbenzoyl-          amino)-8-oxynaphthalin-3,6-disulfonsäure        ver=     einigt.  



  Der neue Farbstoff stellt ein blaurotes  Pulver dar, das sich in     Wasser    mit blauroter,  in konzentrierter Schwefelsäure mit blauer  Farbe löst und Wolle aus essigsaurem Bade  in reinen blaustichig roten Tönen von hervor  ragender Wasch- und     Walkechtheit    und guter       Liehtechtheit    färbt.  



  Die dem vorliegenden Verfahren als     Aus-          gangsstoff    dienende     1-(4'-Tertiärbutylbenzoyl-          amino)-8-oxynaphthalin-3,6-disulfonsäure    kann  beispielsweise erhalten werden, indem man     1-          Amino-8-oxynaphthalin-3,6-disulfonsäure    an  der     Aminogruppe    mit einem     p-Tertiärbutyl-          benzoesäurehalogenid        acyliert.     



  Die Kupplung kann nach an sich bekann  ten Methoden in alkalischem, z. B. in     natrium-          earbonathaltigem    Medium erfolgen.  



  <I>Beispiel:</I>  In einer Lösung von 27 Teilen des     Di-          natriumsalzes    der 1-(4'-Tertiärbutylbenzoyl-         amino)    - 8 -     oxynaphthalin-3,6-disulfonsäure    in  400 Teilen Wasser, welche mit 200 Teilen  einer 10      /oigen        Natriumcarbonatlösung    ver  mischt wurde, tropft man bei 0     bis    5  die auf  übliche Weise dargestellte     Diazolösung    aus  9,

  7 Teilen     2-Amino-l-methoxy-4-tertiäramyl-          benzol.    Der sofort entstehende Farbstoff wird  nach einigen Stunden     abfiltriert    und     zur    Rei  nigung in heissem Wasser gelöst. Die heisse  Lösung wird     geklärt,    und der Farbstoff     wird     durch Zusatz von gesättigter     Natriumchlorid-          lösung    zum grössten Teil in der Hitze wieder  ausgefällt,     abfiltriert    und getrocknet..



  <B> Process for the production of </B> a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 2-amino-1-methoxy-4-tertiary amylbenzene is mixed with 1- (4'-tert-butylbenzoyl-amino) -8-oxynaphthalene-3,6- disulfonic acid combined.



  The new dye is a blue-red powder that dissolves in water with blue-red color, in concentrated sulfuric acid with blue color and colors wool from acetic acid bath in pure blue-tinged red shades of excellent wash and milled fastness and good light fastness.



  The 1- (4'-tert-butylbenzoylamino) -8-oxynaphthalene-3,6-disulfonic acid used as starting material for the present process can be obtained, for example, by adding 1-amino-8-oxynaphthalene-3,6-disulfonic acid acylated the amino group with a p-tert-butylbenzoic acid halide.



  The coupling can after per se known methods in alkaline, z. B. in sodium earbonate medium.



  <I> Example: </I> In a solution of 27 parts of the disodium salt of 1- (4'-tert-butylbenzoyl-amino) -8-oxynaphthalene-3,6-disulfonic acid in 400 parts of water, which is mixed with 200 parts of a 10% sodium carbonate solution was mixed, the diazo solution prepared in the usual way from 9 is added dropwise at 0 to 5,

  7 parts of 2-amino-1-methoxy-4-tertiaryamylbenzene. The dye which forms immediately is filtered off after a few hours and dissolved in hot water for cleaning. The hot solution is cleared and the dye is for the most part precipitated again in the heat by adding saturated sodium chloride solution, filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Monoa.zo- farbstoffes, dadurch gekennzeichnet, dass man dianotiertes 2-Amino-l-methoxy-4-tertiäramyl- benzol mit 1-(4'-Tertiärbutylbenzoyl-amino)-8- oxynaphthalin-3,6-disulfonsäure vereinigt. Der neue Farbstoff stellt ein blaurotes Pulver dar, das sich in Wasser mit blauroter, in konzentrierter Schwefelsäure mit blauer Farbe löst und Wolle aus essigsaurem Bade in reinen blaustiehig roten Tönen von hervor ragender Wasch- und Walkechtheit und guter Lichtechtheit färbt. Claim: Process for the production of a Monoa.zo- dye, characterized in that dianotated 2-amino-1-methoxy-4-tertiary amylbenzene with 1- (4'-tert-butylbenzoyl-amino) -8-oxynaphthalene-3,6 -disulfonic acid combined. The new dye is a blue-red powder that dissolves in water with blue-red color, in concentrated sulfuric acid with blue color and colors wool from acetic acid bath in pure blue-tinged red shades of excellent wash and milled fastness and good light fastness.
CH309776D 1951-10-16 1951-10-16 Process for the preparation of a monoazo dye. CH309776A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH293115T 1951-10-16
CH309776T 1951-10-16

Publications (1)

Publication Number Publication Date
CH309776A true CH309776A (en) 1955-09-15

Family

ID=25733335

Family Applications (1)

Application Number Title Priority Date Filing Date
CH309776D CH309776A (en) 1951-10-16 1951-10-16 Process for the preparation of a monoazo dye.

Country Status (1)

Country Link
CH (1) CH309776A (en)

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