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CH259352A - Process for the preparation of an anthraquinone derivative. - Google Patents

Process for the preparation of an anthraquinone derivative.

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Publication number
CH259352A
CH259352A CH259352DA CH259352A CH 259352 A CH259352 A CH 259352A CH 259352D A CH259352D A CH 259352DA CH 259352 A CH259352 A CH 259352A
Authority
CH
Switzerland
Prior art keywords
blue
anilido
amino
derivative
exchangeable
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 CH259352A publication Critical patent/CH259352A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/56Mercapto-anthraquinones
    • C09B1/58Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
    • C09B1/60Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aliphatic, cycloaliphatic or araliphatic radicals
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl 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. 253480.    Verfahren zur Herstellung eines     Anthraehinonabkömmlings.       Es wurde gefunden, dass ein wertvoller       Anthrachinonabkömmling    hergestellt werden  kann, wenn man ein in     2-,Stellung    einen aus  tauschbaren     Substituenten        enthaltendes        1-          Amino-4-anilido-anthra,chinon    mit Mitteln  behandelt, die den austauschbaren     Substi-          tuenten    durch eine     Merkaptogruppe    zu erset  zen imstande sind und hierauf mit Mitteln,  die die     ss,

  y-Dioxypropylgruppe    einzuführen  imstande sind.  



  Der neue     Anthrachinonabkömmling,    der  1-     Amino    -     -anilido        =anthrachinon@-        2-(ss,y-di-          oxypropyl)-thioäther    ist ein dunkelblaues  Pulver, das sich in     konz.        Schwefelsäure,    ganz  verdünnt mit schmutzig     grünlichblauer,    bei       höherer    Konzentration mit     rotstichig    blauer  Farbe und in Aceton mit blauer Farbe löst  und     Acetatkunstseide    in kräftigen und licht  echten blauen Tönen färbt.  



  Die als Ausgangsstoffe verwendeten 1  Amino-4-anilido-anthrachinone können als       austauschbare        Substituenten    in     2-Stellung     beispielsweise ein Halogenatom, insbesondere  ein Bromatom, oder eine     Sulfonsäuregruppe,          enthalten.    Als Mittel, die den austauschbaren       Substituenten    durch eine     lvlerkaptogruppe    zu       ersetzen    imstande sind, kommen beispiels  weise     Schwefelalkalien    in Betracht, und zur  Einführung der     ss,y-Dioxypropylgruppe    ist  beispielsweise     Glyzerinchlorhydrin    brauch  bar.  



  Die Durchführung der Reaktion kann in  an sich     bekannter    Weise zum Beispiel in alko-         holischem,    wässerigem oder gemischt     alkoho-          lisch-wässerigem        Medium,    offen. oder unter  Druck vorgenommen werden.

      <I>Beispiel:</I>  100 g 1-     Amino    -- 4 -     anilido-2-bromanthra-          ehinon    werden zusammen mit 300 cm' Me  thylalkohol, 75 cm' Wasser, 0,75 g Soda,  200     em3        Natriumsulfhydratlösung    mit einem  Gehalt an 24,6     Vol.-    %     -j--    3,6 %     Na2S,    100 cm'  40     Vol.-%iger    Natronlauge und 50 g Schwe  fel 5 Stunden in einem     Eisenautoklaven    auf  90  erhitzt.

   Man     destilliert    den Alkohol ab,  spült mit 400     cm2    1 %     iger        Sodalösung    nach,  fällt das     Merkaptan    mit 200 g     Kochsalz    aus,  kühlt wenn nötig auf 10 bis 15  und filtriert.  Das Filtrat ist nur schwach gefärbt, aber  nicht mehr blau. Man wäscht mit 800 cm'  einer Lösung von 20 % Kochsalz und 1  Soda. frei von     S-Ionen    (Probe mit     Bleiacetat).     



  Hierauf wird das     Merkaptan    sofort in  1000 cm' 1 %     iger        Sodalösung    mit 30     cm'          Glyzerinchlorhydrin    erwärmt, bis die Lösung  farblos wird (bei etwa 70 ), worauf man fil  triert und mit. Wasser kalt     auswäscht.  



  <B> Additional patent </B> to the main patent No. 253480. Process for the production of an anthraquinone derivative. It has been found that a valuable anthraquinone derivative can be produced if a 1-amino-4-anilido-anthra-quinone containing one of exchangeable substituents in the 2-, position is treated with agents which add a mercapto group to the exchangeable substituents are able to replace and then with funds that the SS,

  are able to introduce y-dioxypropyl group.



  The new anthraquinone derivative, the 1- amino - -anilido = anthraquinone @ - 2- (ss, y-di-oxypropyl) -thioether is a dark blue powder which is in conc. Sulfuric acid, completely diluted with dirty greenish-blue, dissolves in a higher concentration with a reddish blue color and in acetone with a blue color and dyes acetate silk in strong and light blue tones.



  The 1-amino-4-anilido-anthraquinones used as starting materials can contain, for example, a halogen atom, in particular a bromine atom, or a sulfonic acid group, as exchangeable substituents in the 2-position. Suitable agents which are capable of replacing the exchangeable substituent with an intercapto group are, for example, alkaline sulfur, and glycerol chlorohydrin, for example, can be used to introduce the ε, γ-dioxypropyl group.



  The reaction can be carried out in a manner known per se, for example in an alcoholic, aqueous or mixed alcoholic-aqueous medium, open. or under pressure.

      <I> Example: </I> 100 g 1-amino-4-anilido-2-bromanthrahinone are mixed with 300 cm 'methyl alcohol, 75 cm' water, 0.75 g soda, 200 em3 sodium sulfhydrate solution with a Content of 24.6% by volume - 3.6% Na2S, 100 cm '40% by volume sodium hydroxide solution and 50 g sulfur heated to 90 for 5 hours in an iron autoclave.

   The alcohol is distilled off, rinsed with 400 cm2 of 1% soda solution, the mercaptan is precipitated with 200 g of table salt, cooled to 10 to 15 if necessary and filtered. The filtrate is only slightly colored, but no longer blue. It is washed with 800 cm 'of a solution of 20% table salt and 1 soda. free of S ions (sample with lead acetate).



  The mercaptan is then immediately heated in 1000 cm '1% sodium carbonate solution with 30 cm' glycerol chlorohydrin until the solution becomes colorless (at about 70), whereupon it is filtered and with. Washes cold water.

 

Claims (1)

PATENTANSPRUCH: Verfahren: zur Herstellung eines Anthra- chinonabkömmlings, dadurch gekennzeichnet., dass man ein in 2-Stellung einen austaussch- baren Substituenten enthaltendes 1-Amino-4- anilido-anthrachinon mit Mitteln behandelt, die den austauschbaren Subätituenten, durch eine Merkaptogruppe zu ersetzen imstande sind und hierauf mit .Mitteln, die die ss,y-Di- ogypropylgruppe , PATENT CLAIM: Process: for the production of an anthrachinone derivative, characterized in that a 1-amino-4-anilido-anthraquinone containing an exchangeable substituent in the 2-position is treated with agents which add the exchangeable substituents to are able to replace and thereupon with .Means that the ss, y-di- ogypropyl group, einzuführen imstande sind. Der neue Anthraehinonabkömmling, der 1-Amino-4-anilido-anthraclhinon-2-(ss,y-diogy- propyl)-thioäther, ist ein dunkelblaues. Pul ver, das sich in konz. Schwefelsäure, ganz verdünnt mit schmutzig grünlichblauer, bei höherer Konzentration. mit rotstichig blauer Farbe und in Aceton mit blauer Farbe löst und Acetatkunstseide in kräftigen und licht echten blauen Tönen färbt. are able to introduce. The new anthraquinone derivative, the 1-amino-4-anilido-anthraclhinon-2- (ss, y-diogypropyl) -thioether, is a dark blue one. Powder that is in conc. Sulfuric acid, completely diluted with dirty greenish-blue, at a higher concentration. dissolves with a reddish blue color and in acetone with blue color and dyes acetate artificial silk in strong and light blue tones.
CH259352D 1944-01-13 1944-01-13 Process for the preparation of an anthraquinone derivative. CH259352A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH259352T 1944-01-13
CH253480T 1944-01-13

Publications (1)

Publication Number Publication Date
CH259352A true CH259352A (en) 1949-01-15

Family

ID=25729761

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259352D CH259352A (en) 1944-01-13 1944-01-13 Process for the preparation of an anthraquinone derivative.

Country Status (1)

Country Link
CH (1) CH259352A (en)

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