CH268443A - Process for the preparation of an anthraquinone dye. - Google Patents

Process for the preparation of an anthraquinone dye.

Info

Publication number
CH268443A
CH268443A CH268443DA CH268443A CH 268443 A CH268443 A CH 268443A CH 268443D A CH268443D A CH 268443DA CH 268443 A CH268443 A CH 268443A
Authority
CH
Switzerland
Prior art keywords
anthraquinone dye
preparation
dye
parts
amino
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 CH268443A publication Critical patent/CH268443A/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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/516—N-acylated derivatives
    • C09B1/5165—N-acylated derivatives only amino and hydroxy groups

Landscapes

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 265846.    Verfahren zur Herstellung eines     Anthrachinonfarbstoffes.       Es wurde gefunden, dass ein wertvoller       Anthrachinonfarbstoff    hergestellt werden  kann, wenn man     1-Amino-8-oxy        anthraehinon     derart mit einem     propionylierenden    Mittel be  handelt, dass die     Aminogruppe        propionyliert     wird.  



  Der neue Farbstoff bildet gelbe Kristalle  und färbt nach geeigneter     Verpastung    Acetat  kunstseide in lichtechten gelben Tönen.  



  Als     propionylierende    Mittel können gemäss  vorliegendem Verfahren zum Beispiel reak  tionsfähige, funktionelle Derivate der     Pro-          pionsäure,    insbesondere das     Propionsäurechlo-          rid,    verwendet werden.  



  Die Reaktion kann nach an sich bekannten  Methoden beispielsweise in einem indifferen  ten Medium, wie     Pyridin    oder andern ter  tiären Basen, Aceton, Nitrobenzol, Chlorben  zol usw., oder     gewünschtenfalls    auch in einem       Überschuss    des als Lösungs- bzw. Verteilungs  mittel wirkenden     Acylierungsmittels    vorge  nommen werden. Zweckmässig führt man die  Reaktion bei erhöhter Temperatur durch.  



  Da beim vorliegenden Ausgangsstoff die       Aminogruppe    ganz unvergleichlich viel leich  ter     acyliert    wird als die     Hydroxylgruppe,    be-    darf es bei üblichen     Acylierungsbedingungen     keinerlei besonderer Massnahmen, um die Re  aktion im angegebenen Sinne zu lenken.  



       Beispiel:     Man erwärmt 2,2 Teile     Propionsäure    in 30  Teilen     o-Dichlorbenzol    und 3,6 Teilen     Thio-          ny        lchlorid    zwei Stunden auf 701, steigert die  Temperatur auf 1200 und gibt 6,6 Teile     Di-          methylanilin    und 6 Teile     1-Amino-8-oxy-          anthrachinon    zu. Nach etwa einer halben  Stunde lässt man auf Zimmertemperatur ab  kühlen und filtriert, den Farbstoff ab. Zur  besseren     Abscheidung    des Farbstoffes kann  man 60 bis 100 Teile Methanol zufügen.



  <B> Additional patent </B> to main patent no. 265846. Process for the production of an anthraquinone dye. It has been found that a valuable anthraquinone dye can be produced by treating 1-amino-8-oxy anthraehinone with a propionylating agent in such a way that the amino group is propionylated.



  The new dye forms yellow crystals and, after suitable pasting, colors acetate rayon in lightfast yellow tones.



  According to the present process, for example reactive, functional derivatives of propionic acid, in particular propionic acid chloride, can be used as propionylating agents.



  The reaction can be carried out by methods known per se, for example in an indifferent medium such as pyridine or other tertiary bases, acetone, nitrobenzene, chlorobenzene, etc., or, if desired, in an excess of the acylating agent acting as a solvent or distribution agent will. The reaction is expediently carried out at an elevated temperature.



  Since the amino group in the present starting material is acylated incomparably more easily than the hydroxyl group, no special measures are required under normal acylation conditions in order to direct the reaction in the stated sense.



       Example: 2.2 parts of propionic acid in 30 parts of o-dichlorobenzene and 3.6 parts of thionyl chloride are heated to 701 for two hours, the temperature is increased to 1200 and 6.6 parts of dimethylaniline and 6 parts of 1-amino 8-oxy-anthraquinone too. After about half an hour, the mixture is allowed to cool to room temperature and filtered, and the dye is removed. For better separation of the dye, 60 to 100 parts of methanol can be added.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Anthra- chinonfarbstoffes, dadurch gekennzeichnet, dass man 1-Amino-8-oxyanthrachinon derart mit einem propionylierenden Mittel behandelt, dass die Aminogruppe propionyliert wird. Der neue Farbstoff bildet feine gelbe Kri stalle und färbt nach geeigneter Verpastung Acetatkunstseide in kräftigen lichtechten gel ben Tönen. Claim: Process for the production of an anthraquinone dye, characterized in that 1-amino-8-oxyanthraquinone is treated with a propionylating agent in such a way that the amino group is propionylated. The new dye forms fine yellow crystals and, after suitable pasting, dyes acetate artificial silk in strong, lightfast yellow tones.
CH268443D 1946-08-07 1946-08-07 Process for the preparation of an anthraquinone dye. CH268443A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH265846T 1946-08-07
CH268443T 1946-08-07

Publications (1)

Publication Number Publication Date
CH268443A true CH268443A (en) 1950-05-15

Family

ID=25730834

Family Applications (1)

Application Number Title Priority Date Filing Date
CH268443D CH268443A (en) 1946-08-07 1946-08-07 Process for the preparation of an anthraquinone dye.

Country Status (1)

Country Link
CH (1) CH268443A (en)

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