CH212808A - Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. - Google Patents

Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative.

Info

Publication number
CH212808A
CH212808A CH212808DA CH212808A CH 212808 A CH212808 A CH 212808A CH 212808D A CH212808D A CH 212808DA CH 212808 A CH212808 A CH 212808A
Authority
CH
Switzerland
Prior art keywords
tetrahydroanthraquinone
nitrogen
derivative
preparation
leuco
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 CH212808A publication Critical patent/CH212808A/en

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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
    • C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
    • 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
    • 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
    • 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
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     stickstoffhaltigen        6.6.7.8-Tetrahydro-          anthrachinonderivates.       Gegenstand dieses Zusatzpatentes ist ein  Verfahren zur Herstellung eines stickstoff  haltigen     5.6.7.8-Tetrahydroanthrachinon-          derivates,    welches darin besteht, dass man       Leuko    - 5.6.7.8 -     tetrahydrochinizarin    mit  einem Gemisch von     Methylamin    und     Og-          äthylamin    umsetzt und die     Leukoverbin-          dung    oxydiert.  



  Die so erhaltene neue Verbindung hat  einen Schmelzpunkt von 198 bis 200' C. Sie  löst sich in konzentrierter Schwefelsäure mit  roter Farbe. Der Farbstoff färbt Acetat  seide in     grünstichig    blauen Tönen.  



  <I>Beispiel:</I>  Das Gemisch von 25 Gewichtsteilen       Leuko-5.6.7.8-tetrahydrochinizarin,    100  Gewichtsteilen Äthylalkohol, 7 Gewichtstei  len einer 50     %        igen,        wässrigen        Methylamin-          lösung    und 7 Gewichtsteilen     Ogäthylamin            wird    5 Stunden unter     Rückfluss    gekocht. Zu  der braunen Lösung fügt man 1 Gewichts  teil     Piperidin    und     lei et    Luft ein, bis die       Dehydrierung    beendet ist.

   Aus der blauen  Lösung scheidet sich beim Erkalten das       1-Methylamino-4-ogäthylamino-    5 . 6. 7.     8-te-          trahydroanthrachinon    in fein kristalliner  Form ab. Es schmilzt nach     dein        Umkristal-          lisieren    aus     Butanol    bei 198 bis 200' C. In  konzentrierter Schwefelsäure löst es sich mit  roter Farbe, in organischen Lösungsmitteln  mit blauer Farbe.     Acetatseide    wird in grün  stichig blauen Tönen gefärbt.



  Process for the production of a nitrogen-containing 6.6.7.8-tetrahydro-anthraquinone derivative. The subject of this additional patent is a process for the production of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative, which consists in reacting leuco - 5.6.7.8 - tetrahydroquinizarine with a mixture of methylamine and ogethylamine and oxidizing the leuco compound.



  The new compound thus obtained has a melting point of 198 to 200 ° C. It dissolves in concentrated sulfuric acid with a red color. The dye dyes acetate silk in greenish blue tones.



  <I> Example: </I> The mixture of 25 parts by weight of leuco-5.6.7.8-tetrahydroquinizarin, 100 parts by weight of ethyl alcohol, 7 parts by weight of a 50% aqueous methylamine solution and 7 parts by weight of ogäthylamine is refluxed for 5 hours. 1 part by weight of piperidine is added to the brown solution and air is let in until the dehydration has ended.

   The 1-methylamino-4-ogäthylamino-5 separates from the blue solution on cooling. 6. 7. 8-tetrahydroanthraquinone in finely crystalline form. After recrystallizing from butanol, it melts at 198 to 200 ° C. It dissolves in concentrated sulfuric acid with a red color, in organic solvents with a blue color. Acetate silk is dyed in green, blue tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick stoffhaltigen 5<B>.6</B> .7.8-Tetrahydroanthrachi- nonderivates, dadurch gekennzeichnet, dass man Leuko - 5 . 6 . 7 . 8 -tetrahydrochinizarin mit einem Gemisch von Methylamin und 0g- äthylamin umsetzt und die Leukoverbindung oxydiert. Die so erhaltene neue Verbindung hat einen Schmelzpunkt von 198 bis ?00 C. Sie löst sich in konzentrierter Sch-,vefelsäure mit roter Farbe. PATENT CLAIM: Process for the production of a nitrogen-containing 5 <B> .6 </B> .7.8-tetrahydroanthraquinone derivative, characterized in that leuco - 5. 6th 7th 8-tetrahydroquinizarin is reacted with a mixture of methylamine and 0g ethylamine and the leuco compound is oxidized. The new compound thus obtained has a melting point of 198 to? 00 C. It dissolves in concentrated sulfuric acid with a red color. Per Farbstoff färbt Aeetat- seide in grünstichig blauen Tönen. Aetetate silk dyes in greenish blue tones with a dye.
CH212808D 1937-12-24 1938-12-17 Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. CH212808A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE212808X 1937-12-24
DE150138X 1938-01-15
CH210607T 1938-12-17

Publications (1)

Publication Number Publication Date
CH212808A true CH212808A (en) 1940-12-15

Family

ID=27177905

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212808D CH212808A (en) 1937-12-24 1938-12-17 Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative.

Country Status (1)

Country Link
CH (1) CH212808A (en)

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