CH203430A - Process for the preparation of a dye of the anthraquinone series. - Google Patents

Process for the preparation of a dye of the anthraquinone series.

Info

Publication number
CH203430A
CH203430A CH203430DA CH203430A CH 203430 A CH203430 A CH 203430A CH 203430D A CH203430D A CH 203430DA CH 203430 A CH203430 A CH 203430A
Authority
CH
Switzerland
Prior art keywords
anthraquinone
mixture
amino
leuco compounds
dye
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH203430A publication Critical patent/CH203430A/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
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/285Dyes with no other substituents than the amino groups

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

Description

  

  Verfahren zur Herstellung eines     Farbstoffes    der     Anthrachinonreihe.       Es wurde gefunden, dass man einen wert  vollen, neuen Farbstoff der     Anthrachinon-          reihe    erhält, wenn man     Anthrachinonabkömm-          linge    vom allgemeinen Aufbau  
EMI0001.0007     
    worin X und Y austauschfähige Reste be  deuten, die die     Überführung    der     Anthrachi-          nonabkömmlinge    in ihre     Leukoverbindungen     gestatten, wie z. B.

   OH,     0-Alkyl    oder     NH2,     teilweise in Form ihrer     Leukoverbindungen     mit einem Gemisch von     Amino-2,3-propan-          diol    und     Aminoäthanol    umsetzt. Der so er  haltene Endstoff wird, da er zum Teil in  Form seiner     Leukoverbindung    vorliegt, nach  träglich oxydiert.  



  Ausgangsstoffe sind zum Beispiel 1,4-Di-         oxyanthrachinon,        1,4-Diaminoanthrachinon,          1-Amino-4-oxyanthrachinon,        1-Amino-4-me-          thoxyanthrachinon,        1-Ogy-4-methoxyanthra-          chinon    und     1,4-Dimethogyanthrachinon.     



  In     vielen    Fällen ist es nicht erforderlich,  von den     fertigen        Leukoverbindungen    auszu  gehen, sondern man kann auch die     Anthra-          cIiinonabkömmlinge    in Gegenwart eines Re  duktionsmittels, wie     Zinkstaub    oder     Na-          triumhydrosulfit,        verwenden.     



  Der so erhaltene Endstoff liefert auf       Celluloseestern    und     -äthern        Färbungen    von  hoher Klarheit und guter Echtheit. Ein be  sonderer Vorzug liegt in seiner guten Was  serlöslichkeit, so dass man beim Färben aus  wässerigem Bad vielfach ohne Zusatz von       verteilend    oder netzend wirkenden oder an  dern     Färbereihilfsmitteln    auskommt.  



  <I>Beispiel:</I>  Eine Mischung von 24 Teilen     1,4-Dioxy-          anthrachinon,    6 Teilen Leuko-1,4-dioxy-           anthrachinon    und 160 Teilen     Isobutanol    wird  bei 60   C     unter    Rühren mit einer Mischung  von 13,6 Teilen     1-Amino-2,3-propandiol    und  9,2 Teilen     Aminoäthanol    versetzt.

   Das Ge  misch rührt man zunächst 2 Stunden lang bei  60   C, erhitzt es dann zum Sieden und kocht  es so lange     unter    Rühren und     Rückflussküh-          lung,    bis in einer Probe kein     1,4-Dioxy-          anthra.chinon    mehr nachweisbar ist. Zur  Oxydation     geringer    Mengen     Leukoverbin-          dung    leitet man Luft durch das Gemisch  und befreit es mittels Wasserdampf vom       Isobutanol,    wobei die Hauptmenge der ent  standenen Verbindung mit blauer Farbe in  Lösung geht.  



  Nach Zugabe von Tierkohle filtriert man  von geringen Mengen ungelöster Anteile ab  und salzt den entstandenen Stoff aus der  tiefblauen Mutterlauge nach Zugabe von  etwas Natronlauge mit Kochsalz aus. Er be  steht aus einem Gemisch von hauptsächlich       1-Propandiol    -     amino    -4 -     äthanola.minoanthra          chinon    und wenig     1,4-Dipropa.ndi.olamino-          anthraehinon,    während das gleichfalls in ge  ringer     -Menge    entstandene wasserunlösliche       1,4-Di-(äthanolamino)-anthra.chinon    durch  Filtrieren der     wässrigen    Lösung als wasser  unlöslicher Anteil abgetrennt wird.  



  Der so     erhaltene    blaue Farbstoff löst sich  in Schwefelsäure mit blaustichig roter Farbe.  In     warmem    Wasser löst er sich mit tief  blauer Farbe und liefert auf     Celluloseäthern     und     -estern    kräftige blaue Färbungen von  hervorragender Echtheit.



  Process for the preparation of a dye of the anthraquinone series. It has been found that a valuable, new dye of the anthraquinone series is obtained if anthraquinone derivatives of the general structure are used
EMI0001.0007
    where X and Y are interchangeable residues that allow the conversion of the anthraquinone derivatives into their leuco compounds, such as. B.

   OH, O-alkyl or NH2, partly in the form of their leuco compounds, with a mixture of amino-2,3-propanediol and aminoethanol. The end product thus obtained is, since it is partly in the form of its leuco compound, subsequently oxidized.



  Starting materials are, for example, 1,4-dioxyanthraquinone, 1,4-diaminoanthraquinone, 1-amino-4-oxyanthraquinone, 1-amino-4-methoxyanthraquinone, 1-Ogy-4-methoxyanthraquinone and 1,4- Dimethogyanthraquinone.



  In many cases it is not necessary to start from the finished leuco compounds, but the anthraciinone derivatives can also be used in the presence of a reducing agent such as zinc dust or sodium hydrosulfite.



  The end product thus obtained provides colorations of high clarity and good fastness on cellulose esters and ethers. A particular advantage is its good solubility in water, so that dyeing from an aqueous bath often does not require the addition of dispersing or wetting agents or other dyeing auxiliaries.



  <I> Example: </I> A mixture of 24 parts of 1,4-dioxy-anthraquinone, 6 parts of leuco-1,4-dioxy-anthraquinone and 160 parts of isobutanol is mixed with a mixture of 13.6 at 60 ° C. while stirring Parts of 1-amino-2,3-propanediol and 9.2 parts of aminoethanol are added.

   The mixture is first stirred for 2 hours at 60 C, then heated to the boil and boiled while stirring and refluxing until no more 1,4-dioxyanthraquinone can be detected in a sample. In order to oxidize small amounts of leuco compounds, air is passed through the mixture and isobutanol is removed from it by means of steam, with the majority of the resulting compound dissolving with a blue color.



  After adding animal charcoal, small amounts of undissolved fractions are filtered off and the resulting substance is salted out from the deep blue mother liquor after adding a little sodium hydroxide solution with common salt. It consists of a mixture of mainly 1-propanediol - amino -4 - äthanola.minoanthraquinone and a little 1,4-Dipropa.ndi.olaminoanthraehinone, while the water-insoluble 1,4-di- (Ethanolamino) anthraquinone is separated off as a water-insoluble fraction by filtering the aqueous solution.



  The blue dye thus obtained dissolves in sulfuric acid with a bluish red color. In warm water it dissolves with a deep blue color and, on cellulose ethers and esters, provides strong blue colorations of excellent fastness.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Farbstoffes der Anthrachinonreihe, dadurch gekennzeichnet, dass man Anthraehinon- abkömmlinL):e vorn allzemeinen Aufbau EMI0002.0032 worin X und Y austauschfähige Reste be deuten, die die Überführung der Anthrachi- nonahkömmlinge in ihre Leukoverbindungen gestatten teilweise in Form ihrer Leukover- bindungen, mit einem Gemisch von Amino- 2, PATENT CLAIM: Process for the production of a new dye of the anthraquinone series, characterized in that anthraquinone is derived from L): e from the general structure EMI0002.0032 where X and Y mean exchangeable residues which allow the conversion of the anthraquinone derivatives into their leuco compounds, partly in the form of their leuco compounds, with a mixture of amino 2, 3-propandiol und Aminoäthanol umsetzt, und vorhandene Leukoverbindungen oxy diert. Der neue Farbstoff ist ein Gemisch von l.- Propandiol -amino - 4 - äthanolaminoanthrachi- non und 1,4-Dipropandiola.minoanthrachinon. Er löst sich in Schwefelsäure mit blaustichig roter Farbe. In warmem Wasser ist er mit tiefblauer Farbe löslich und liefert auf Cel- luloseestern und -äthern kräftige blaue Fär bungen von hervorragender Echtheit. 3-propanediol and aminoethanol converts, and existing leuco compounds oxy dated. The new dye is a mixture of 1.-Propanediol -amino-4-Ethanolaminoanthraquinone and 1,4-Dipropanediola.minoanthraquinone. It dissolves in sulfuric acid with a bluish red color. It is soluble in warm water with a deep blue color and, on cellulose esters and ethers, provides strong blue colorations of excellent fastness.
CH203430D 1936-12-23 1937-11-27 Process for the preparation of a dye of the anthraquinone series. CH203430A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE203430X 1936-12-23

Publications (1)

Publication Number Publication Date
CH203430A true CH203430A (en) 1939-03-15

Family

ID=5776390

Family Applications (1)

Application Number Title Priority Date Filing Date
CH203430D CH203430A (en) 1936-12-23 1937-11-27 Process for the preparation of a dye of the anthraquinone series.

Country Status (1)

Country Link
CH (1) CH203430A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2060048A2 (en) * 1969-07-18 1971-06-11 Sandoz Sa

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2060048A2 (en) * 1969-07-18 1971-06-11 Sandoz Sa

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