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CH159409A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH159409A
CH159409A CH159409DA CH159409A CH 159409 A CH159409 A CH 159409A CH 159409D A CH159409D A CH 159409DA CH 159409 A CH159409 A CH 159409A
Authority
CH
Switzerland
Prior art keywords
azo dye
production
parts
new azo
new
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH159409A publication Critical patent/CH159409A/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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0808—Amino benzenes free of acid groups characterised by the amino group unsubstituted amino group
    • 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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • C09B43/128—Aliphatic, cycloaliphatic or araliphatic 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
    • C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    erhält, wenn man     4-Methoxy-l-dia-          zobenzol    in einem wässerigen Medium, dessen  p H nicht grösser als 7 ist, auf     1-Amino-3-          oxybenzol    einwirken lässt und das erhaltene  Produkt nachträglich     acetyliert.     



  Der so hergestellte Farbstoff ist ein dun  kelgelbes Pulver, das sich in organischen  Lösungsmitteln, wie Alkohol,     Essigssäure-          ester,    mit gelber Farbe löst und Zellulose  ester und     -äther    in sehr echten     grünstichig     gelben, nicht Phototropen Tönen anfärbt.  Der     Farbstoff    eignet sich insbesondere zur  Erzielung lichtechter Mischtöne.    <I>Beispiel:</I>  123 Teile     4-AZethoxy-l-aminobenzol    wer  den in 1500 Teilen Wasser und 250 Teilen  30     %iger    Salzsäure gelöst.

   Man fügt 500  Teile Eis zu und     diazotiert    mit 70 Teilen       Natriumnitrit.    Die     Diazolösung    wird mit 136  Teilen     Natriumacetat    versetzt und mit einer  Auflösung von 109 Teilen     m-Aminophenol     in verdünnter Salzsäure vereinigt. Nachdem  die Kupplung     dureh    eventuelles weiteres Zu-    fügen von     Natriumacetat    zu Ende geführt  wurde,     filtriert    man ab, wäscht mit Wasser  neutral und trocknet.  



  219 Teile des so erhaltenen Produktes  werden mit 102 Teilen     Essigsäureanhydrid          '/4    Stunde auf<B>1000</B> erwärmt. Hierauf wird  im Vakuum getrocknet. Der gebildete Farb  stoff kann gegebenenfalls aus Eisessig um  kristallisiert werden.



  Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 4-methoxy-1-dia- zobenzene is allowed to act on 1-amino-3-oxybenzene in an aqueous medium whose pH is not greater than 7 and the product obtained subsequently acetylated.



  The dye produced in this way is a dark yellow powder that dissolves in organic solvents such as alcohol, acetic acid ester, with a yellow color and stains cellulose esters and ethers in very real greenish yellow, non-phototropic tones. The dye is particularly suitable for achieving lightfast mixed shades. <I> Example: </I> 123 parts of 4-AZethoxy-1-aminobenzene are dissolved in 1500 parts of water and 250 parts of 30% hydrochloric acid.

   500 parts of ice are added and the mixture is diazotized with 70 parts of sodium nitrite. The diazo solution is mixed with 136 parts of sodium acetate and combined with a solution of 109 parts of m-aminophenol in dilute hydrochloric acid. After the coupling has been completed by any further addition of sodium acetate, it is filtered off, washed neutral with water and dried.



  219 parts of the product thus obtained are heated to <B> 1000 </B> with 102 parts of acetic anhydride / 4 hour. This is followed by drying in a vacuum. The color formed can optionally be crystallized from glacial acetic acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man 4-Methoxy-l-diazobenzol in einem wässe rigen Medium, dessen p H nicht grösser als 7 ist, auf 1-Amino-3-oxybenzol einwirken lässt und das erhaltene Produkt nachträglich ace- tpliert. Der neue Farbstoff bildet ein dunkel gelbes Pulver, das sich in organischen Lö sungsmitteln mit gelber Farbe löst und Zellu- loseester und -äther in echten grünstichig gelben, nicht Phototropen Tönen färbt. Claim: Process for the preparation of a new azo dye, characterized in that 4-methoxy-l-diazobenzene is allowed to act on 1-amino-3-oxybenzene in an aqueous medium, the pH of which is not greater than 7, and the product obtained subsequently ac- cepted. The new dye forms a dark yellow powder which dissolves in organic solvents with a yellow color and colors cellulose esters and ethers in real greenish yellow, non-phototropic tones.
CH159409D 1931-12-21 1931-12-21 Process for the production of a new azo dye. CH159409A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH159409T 1931-12-21

Publications (1)

Publication Number Publication Date
CH159409A true CH159409A (en) 1933-01-15

Family

ID=4413208

Family Applications (1)

Application Number Title Priority Date Filing Date
CH159409D CH159409A (en) 1931-12-21 1931-12-21 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH159409A (en)

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