CH151155A - Process for the preparation of a new dye of the anthraquinone acridone series. - Google Patents

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

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Publication number
CH151155A
CH151155A CH151155DA CH151155A CH 151155 A CH151155 A CH 151155A CH 151155D A CH151155D A CH 151155DA CH 151155 A CH151155 A CH 151155A
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CH
Switzerland
Prior art keywords
preparation
parts
new dye
dye
acid
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 CH151155A publication Critical patent/CH151155A/en

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Description

  

  Verfahren zur Darstellung eines neuen     Farbstoffes   <B>der</B>     Anthraehinonakridoni-eihe.       Im Hauptpatent ist ein Verfahren zur  Darstellung eines neuen Farbstoffes der       Anthrachinonakridonreihe    beschrieben, wel  ches darin besteht-,     dass    man die     1-Tetraehlor-          anilide,   <B>-</B> A<B>-</B>     chloranthra,ehinoni   <B>-</B> 2<B>-</B>     -ca-rbcn#säure     mit wasserentziehenden Mitteln behandelt.  



  Es wurde nun gefunden,     dass    man in ganz  analoger Weise ebenfalls einen neuen Farb  stoff der     Anthrachinonakridonreihe    erhalten  kann, wenn man die     1-Tetraelilo-ranilido-          a,nthrachino-n-2-ea.rbonsäure,    die durch Um  setzung des     1-Chloranthrachinon-2-earbon-          säurebenzylesters    mit 2.<B>3.</B> 4.<B>5 -</B>     Tetrachlor-          anilin    und     Verseifung    des entstandenen  Esters erhalten -werden kann, mit wasserent  ziehenden Mitteln behandelt.  



  Der erhaltene Farbstoff löst sieh in kon  zentrierter Schwefelsäure mit orangegelber  Farbe und liefert eine violette     Küpe,    auf  Baumwolle orangegelbe Färbungen.    <I>Beispiel:</I>  2o Teile     1-Chloranthrachinon-2-corbon-          säurebenzylester    werden mit<B>9</B> Teilen  2.<B>3.</B> 4.<B>5 -</B>     Tetrachloranilin,   <B>6,2</B> Teilen was  serfreiem     Natriumacetat,   <B>0,3</B> Teilen Kupfer  oxyd und<B>25</B> Teilen Nitrobenzol vier Stun  den lang auf<B>18,5</B> bis<B>195 ' C</B> erwärmt.  Nach dem Abkühlen giesst man die Schmelze  in 200 Teile konzentrierte Schwefelsäure,       und    zwar so,     dass    die Temperatur nicht über  <B>50' C</B> steigt.

   Nach einstündigem Rühren  wird die Lösung in Wasser gegeben und das  Nitrobenzol mit Wasserdampf abgeblasen.  Die     zurüekbleibende   <B>1 -</B>     Tetrachloranilido-          anthrachinon-2-earbonsä,ure    wird abgesaugt  und getrocknet.  



  <B>23</B> Teile der Säure werden mit<B>90</B> Teilen  trockenem     Nitrobenzol    und<B>11</B> Teilen     Essig-          säureanhydrid    zwei Stunden lang bei<B>150'</B>     C     verrührt, darauf wird die Schmelze mit<B>90</B>  Teilen trockenem Nitrobenzol verdünnt, wor-      auf man bei<B>95</B> bis<B>100' C -</B> allmählich<B>2,7</B>  Teile konzentrierte Schwefelsäure hinzufügt.  Man hält die Temperatur zirka vier Stunden  lang auf gleicher Höhe,     lässt    darnach er  kalten und saugt das Reaktionsprodukt ab.

    Es wird mit Nitrobenzol gewaschen und un  ter Zugabe von verdünnter     Natranlauge    durch       Wasserdampfdestillation    und     nachfoIgender     Filtration von     Nitrobenzel    und.     alkalilöslichen     Beimengungen befreit.



  Process for the preparation of a new dye <B> the </B> Anthraehinonakridoni series. The main patent describes a process for the preparation of a new dye of the anthraquinone acridone series, which consists in using the 1-tetrahaloranilides, <B> - </B> A <B> - </B> chloranthra, ehinoni < B> - </B> 2 <B> - </B> -ca-rbcn # acid treated with dehydrating agents.



  It has now been found that a new dye of the anthraquinone acridone series can also be obtained in a very analogous manner if the 1-tetraelilo-ranilido- a, nthrachino-n-2-ea.rboxylic acid, which is produced by conversion of 1-chloroanthraquinone, is used -2-earbonic acid benzyl ester with 2. <B> 3. </B> 4. <B> 5 - </B> tetrachloroaniline and saponification of the resulting ester can be treated with dehydrating agents.



  The dye obtained dissolves in concentrated sulfuric acid with an orange-yellow color and gives a violet vat, orange-yellow colorations on cotton. <I> Example: </I> 2o parts of 1-chloroanthraquinone-2-carbonic acid benzyl ester are mixed with <B> 9 </B> parts 2. <B> 3. </B> 4. <B> 5 - < / B> Tetrachloroaniline, <B> 6.2 </B> parts of water-free sodium acetate, <B> 0.3 </B> parts of copper oxide and <B> 25 </B> parts of nitrobenzene for four hours < B> 18.5 </B> to <B> 195 'C </B> heated. After cooling, the melt is poured into 200 parts of concentrated sulfuric acid in such a way that the temperature does not rise above <B> 50 ° C </B>.

   After stirring for one hour, the solution is poured into water and the nitrobenzene is blown off with steam. The remaining <B> 1 - </B> tetrachloroanilido-anthraquinone-2-earboxylic acid is filtered off with suction and dried.



  <B> 23 </B> parts of the acid are mixed with <B> 90 </B> parts of dry nitrobenzene and <B> 11 </B> parts of acetic anhydride for two hours at <B> 150 '</B> C, then the melt is diluted with <B> 90 </B> parts of dry nitrobenzene, whereupon at <B> 95 </B> to <B> 100 'C - </B> one gradually <B> Add 2.7 parts concentrated sulfuric acid. The temperature is kept at the same level for about four hours, then left to cool and the reaction product is filtered off with suction.

    It is washed with nitrobenzene and with the addition of dilute sodium hydroxide solution by steam distillation and subsequent filtration of nitrobenzene and. free of alkali-soluble additions.

Claims (1)

PATENTANSPRUCH., Verfahren zur Darstellung eines Farb stoffes der Anthrachinonakridonreihe, da- durch gekennzeichnet, dass man die 1-Tetra- chloranilidoanthrae,hinon-2-earbonsä,ure, die durch Umsetzung des 1-Clilorantliraehiiion- 2-earbonsä.ur,ebenzylesters mit 2.<B>3.</B> 4.<B>5</B> - Tetraehloranilin und Verseifung des ent standenen Esters hergestellt werden kann, mit wasserentziehenden Mitteln behandelt. PATENT CLAIM., A method for the preparation of a dye of the anthraquinone acridone series, characterized in that the 1-tetra-chloroanilidoanthrae, hinon-2-earboxylic acid, ure obtained by reacting 1-clilorantliraehiiion- 2-earboxylic acid, is also ethyl ester 2. <B> 3. </B> 4. <B> 5 </B> - Tetraehloranilin and saponification of the resulting ester can be produced, treated with dehydrating agents. Der erhaltene Farbstoff löst sich in kon zentrierter Schwefelsäure mit orangegelber Farbe und liefert eine violette Küpe, auf Baumwolle orangegelbe Färbungen. The dye obtained dissolves in concentrated sulfuric acid with an orange-yellow color and gives a violet vat, orange-yellow dyeings on cotton.
CH151155D 1929-04-29 1930-04-08 Process for the preparation of a new dye of the anthraquinone acridone series. CH151155A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE151155X 1929-04-29
CH148493T 1930-04-08

Publications (1)

Publication Number Publication Date
CH151155A true CH151155A (en) 1931-11-30

Family

ID=25715215

Family Applications (1)

Application Number Title Priority Date Filing Date
CH151155D CH151155A (en) 1929-04-29 1930-04-08 Process for the preparation of a new dye of the anthraquinone acridone series.

Country Status (1)

Country Link
CH (1) CH151155A (en)

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