CH235215A - Process for the preparation of an anthraquinone dye. - Google Patents

Process for the preparation of an anthraquinone dye.

Info

Publication number
CH235215A
CH235215A CH235215DA CH235215A CH 235215 A CH235215 A CH 235215A CH 235215D A CH235215D A CH 235215DA CH 235215 A CH235215 A CH 235215A
Authority
CH
Switzerland
Prior art keywords
dye
preparation
anthraquinone dye
parts
weight
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaf Hydrierwerke
Original Assignee
Deutsche Hydrierwerke 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 Deutsche Hydrierwerke Ag filed Critical Deutsche Hydrierwerke Ag
Publication of CH235215A publication Critical patent/CH235215A/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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr.     23026,5.       Verfahren zur     Herstellung    eines     Anthrachinonfarbstoffes.       Das     Hauptpatent        betrifft    ein     Verfalhren     zur     13erstellung    eines     Diacylimd#s,    das da  durch     gekennzeitohnet    ist,

   da ss man     1-Amino-          4-Brom-anthraclhino@n-2@sulfosäure    oder deren       Salze    mit 3 -     Amino    -     benzolsulfon    -     benzol        -          s@ulfonimid        umsetzt.    Die erhaltene neue Ver  bindung stellt in Form ihres     Natriumsalizes     ein in     Wasser    mit     neinblauer    Farbe     leicht          lösliches,        bronzeglänzendes    Pulver dar und  gibt auf Wolle,

   aus     saurem        Bad    ausgefärbt,  sehr lichtechte und     gleichmässige        blaue    Fär  bungen.  



  E.4     wurde    nun gefunden, dass     man,    zu       einem    neuen sauren     Anthrachinonfarbstoff     gelangt, wenn     man        1,4-Di"halogenanthraehi-          non-    6     -oulfo,chlorid    mit 4-     (Melhyliamino,)-          benzoilisulfon    -     m:ethylsulfonimid    -     alkali    um-         setzt,        anschliessend    im     Molverhältnis    1 :

   2 mit       Cyclohexylamin        kondensiert        und,das.Imil    frei  setzt. Der     entstandene        grünblaue        Farbstoff          ;schmilzt    bei 191-192 C und färbt     Wolle     au     ls        sIaurer        Lösiung        in        grünblauen    Farbtönen.  



  Der neue Farbstoff kann     beispielsweise          folgendermassen,d'argestellt    werden:  10     Gewichtsteile        1,4-D@ichloranthrachinon-          6    -     sulfoichliorid,    10     Gewichtsteile    4 -     (M,e        -          thylamino)    -     benzolsulfon    -     m@ethylsulfonimid-          kalium    und 250     Gewichtsteile    trockenes       Xylol    werden     .im    Ölbad 4-5     :

  Stunden        zum     leichten Sieden erhitzt. Nach dem     Erkalten     wird     abgesaugt.    Der erhaltene     Rückstand          wird        im    heissen verdünnten Ammoniak     gelöst          und    mit     Salzsäume        ausgefällt.    Man     erhält,das          Kondensationisprodukt    der Formel  
EMI0001.0086     
    mit dem Schmelzpunkt von 166-167 C.

        5     Gewichtsteile        des    vorgenannten     Iion-          densationsprodul,tes,    0;25     Gewichtsteile    Kup  ferbronze, 0,25     Gewichtsteile        Kupferacelat,     175     Voliunteile        Cyclohexylamin        werden    im  Ölbad     41-Stunden    auf 160  C (Innentempe  ratur)

       .erhitzt.    Nach Beendigung der Reak  tion wird etwas     Kalilau-e        zu-ebehen    und das         übersehüs@sige        Cyc"loliexylaniin    mit -Wasser  dampf     ahgetrieben.    Der erhaltene Farbstoff  kristallisiert beim Erhalten aus und wird in       iibliehe,r        Weise        bereinigt.        Der    Farbstoff be  sitzt     briiril)laue    Farbe und     z@eibt    in Form des  freien     Imid,

  s    den     Seh-melzpunkt        1.91-192''        C.     er     besitzt    die Formel  
EMI0002.0029     
    und färbt;     Wolle    aus .saurer     Lösung    in grün  blauen Farbtönen.



  <B> Additional patent </B> to main patent no. 23026.5. Process for the preparation of an anthraquinone dye. The main patent relates to a process for the production of a diacylimide, which is known to be without

   that 1-amino-4-bromo-anthraclhino @ n-2 @ sulfonic acid or its salts are reacted with 3 - amino - benzenesulfone - benzene - sulfonimide. The new compound obtained, in the form of its sodium salt, is a bronze-shimmering powder that is easily soluble in water with a blue color and gives on wool,

   Colored from an acid bath, very lightfast and evenly colored blue.



  E.4 it has now been found that a new acidic anthraquinone dye is obtained if 1,4-di "halogenanthraehi- non- 6 -oulfo, chloride with 4- (melhyliamino,) - benzoilisulphone - m: ethylsulphonimide - alkali is used - sets, then in a molar ratio of 1:

   2 condensed with cyclohexylamine and, das.Imil sets free. The resulting green-blue dye melts at 191-192 C and dyes wool from an acidic solution in green-blue shades.



  The new dye can, for example, be prepared as follows: 10 parts by weight of 1,4-dichloroanthraquinone-6-sulfoichloride, 10 parts by weight of 4- (M, e-thylamino) -benzenesulfone-m @ ethylsulfonimide potassium and 250 parts by weight of dry xylene in the oil bath 4-5:

  Heated to a gentle boil for hours. After cooling, it is suctioned off. The residue obtained is dissolved in the hot, dilute ammonia and precipitated with salt fringes. The condensation product of the formula is obtained
EMI0001.0086
    with the melting point of 166-167 C.

        5 parts by weight of the aforementioned ionization produle, 0.25 parts by weight of copper bronze, 0.25 parts by weight of copper acelate, 175 parts by volume of cyclohexylamine are heated to 160 C (internal temperature) in an oil bath for 41 hours

       .heated. After the end of the reaction, a little potassium evolves and the excess cyclohexylamine is driven off with water vapor. The dye obtained crystallizes out as it is obtained and is purified in the usual way. The dye is brittle) Color and z @ eibt in the form of the free imide,

  s the melting point 1.91-192 '' C. it has the formula
EMI0002.0029
    and colors; Acid solution wool in green-blue shades.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Anthra- chinonfarbsto,ffes, dadurch --elzennzeielinet, :dass man 1,4-Dih ialobenanthrachi.n.oii-6-:s-iilfo- ch#lo:iid mit 4-:(1VTet@yamino)-benzoisu@fon- methylsulfoni,mi,d-alliali urusetzt, aaschlie- Pend im Molverhältni:5 1 : PATENT CLAIM: Process for the production of an anthrachinone dye, thereby --elzennzeielinet,: that one 1,4-Dih ialobenanthrachi.n.oii-6-: s-iilfo- ch # lo: iid with 4 - :( 1VTet @ yamino) -benzoisu @ fon- methylsulfoni, mi, d-alliali urusetzt, aaschlie- Pend in the molar ratio: 5 1: ? mit Cyelohexyl- amin kondensiert und das Imid freisetzt. Der entstandene b-riinb@laue Farbstoff sehmilzt bei. 1.91-192 C und färbt 'olle aus saurer Lösung in grünblauen Farbtönen. ? condenses with cyelohexyl amine and releases the imide. The resulting b-riinb @ laue dye sehmelzt. 1.91-192 C and stains olle from acidic solution in green-blue shades.
CH235215D 1941-07-09 1942-03-24 Process for the preparation of an anthraquinone dye. CH235215A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE235215X 1941-07-09
DE231803X 1941-12-10
DE140342X 1942-03-14
CH230265T 1942-03-24

Publications (1)

Publication Number Publication Date
CH235215A true CH235215A (en) 1944-11-15

Family

ID=27429727

Family Applications (1)

Application Number Title Priority Date Filing Date
CH235215D CH235215A (en) 1941-07-09 1942-03-24 Process for the preparation of an anthraquinone dye.

Country Status (1)

Country Link
CH (1) CH235215A (en)

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