CH212807A - 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
CH212807A
CH212807A CH212807DA CH212807A CH 212807 A CH212807 A CH 212807A CH 212807D A CH212807D A CH 212807DA CH 212807 A CH212807 A CH 212807A
Authority
CH
Switzerland
Prior art keywords
nitrogen
derivative
tetrahydroanthraquinone
preparation
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 CH212807A publication Critical patent/CH212807A/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

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  • 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       p-(n-Butyl)-anilin    umsetzt und die     Leuko-          verbindung    oxydiert.  



  Die so erhaltene neue Verbindung hat  einen Schmelzpunkt von 99 bis 101   C. Sie  löst sich in konzentrierter Schwefelsäure mit  violetter Farbe. Die daraus durch     Sulfonie-          ren    gebildete     Sulfonsäure    färbt Wolle aus  saurem Bade in grünen Tönen.

      <I>Beispiel:</I>    12 Gewichtsteile     Leuko-5.6.7.8-tetra-          hydrochinizarin    werden mit 100 Gewichts  teilen     p-(n-Butyl)-anilin    und 8 Gewichtstei  len Borsäure     unter    Rühren 3     Stunden    auf  <B>1.00</B> bis 110   C erhitzt.     Dann    leitet man  1 Stunde Luft über oder in die Schmelze und    verdünnt nach dem Abkühlen auf<B>80'</B> C mit  etwa 150 bis 200     Gewichtsteilen    Methanol.  Das Kondensationsprodukt scheidet sich beim  Erkalten kristallin ab. Es wird abgesaugt,  erst mit Methanol, dann mit heissem Wasser  gewaschen.

   Das so gebildete 1     A-Di-(p-n-          butylanilino)-5.    6. 7. 8 -     tetrahydrochinizarin     kristallisiert aus Eisessig in blauen, spiess  förmigen Kristallen vom     Schmelzunpkt    99  bis 101   C. Es löst sich in konzentrierter       Schwefelsäure    mit violetter Farbe. Mit  5 %     igem        Oleum    kann der Farbstoff     sulfo-          niert    werden. Die     Sulfonsäure    färbt Wolle  aus saurem Bade in grünen Tönen von guten  Echtheitseigenschaften.



  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 - tetrahydroquinizarin with p- (n-butyl) aniline and oxidizing the leuco compound.



  The new compound thus obtained has a melting point of 99 to 101 C. It dissolves in concentrated sulfuric acid with a purple color. The sulphonic acid formed from it by sulphoners dyes wool from acid baths in green tones.

      <I> Example: </I> 12 parts by weight of leuco-5.6.7.8-tetra- hydroquinizarin are mixed with 100 parts by weight of p- (n-butyl) -aniline and 8 parts by weight of boric acid while stirring for 3 hours to <B> 1.00 </ B> heated to 110 C. Air is then passed over or into the melt for 1 hour and, after cooling to 80 ° C., diluted with about 150 to 200 parts by weight of methanol. The condensation product separates out in crystalline form on cooling. It is filtered off with suction, washed first with methanol, then with hot water.

   The 1 A-di- (p-n-butylanilino) -5 formed in this way. 6. 7. 8 - tetrahydroquinizarin crystallizes from glacial acetic acid in blue, stick-shaped crystals with a melting point of 99 to 101 C. It dissolves in concentrated sulfuric acid with a violet color. The dye can be sulfonated with 5% oleum. The sulphonic acid dyes wool from an acid bath in green shades with good fastness properties.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick stoffhaltigen 5. 6. 7.8-Tetrahydroanthrachi- nonderivates, dadurch gekennzeichnet, dass man Leuko - 5.6.7.8 -tetrahydrochinizarin mit p-(n-Butyl)-anilin umsetzt und die Leukoverbindung oxydiert. Die so erhaltene neue Verbindung hat einen Schmelzpunkt von 99 bis 101 C. Sie löst sich in konzentrierter Schwefelsäure mit violetter Farbe. Die daraus durch Sulfonie- ren gebildete Sulfonsäure färbt Wolle aus saurem Bade in grünen Tönen. PATENT CLAIM: Process for the production of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative, characterized in that leuco - 5.6.7.8 -tetrahydroquinizarin is reacted with p- (n-butyl) aniline and the leuco compound is oxidized. The new compound thus obtained has a melting point of 99 to 101 C. It dissolves in concentrated sulfuric acid with a purple color. The sulphonic acid formed from it by sulphoners dyes wool from acid baths in green tones.
CH212807D 1937-12-24 1938-12-17 Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. CH212807A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE212807X 1937-12-24
DE150138X 1938-01-15
CH210607T 1938-12-17

Publications (1)

Publication Number Publication Date
CH212807A true CH212807A (en) 1940-12-15

Family

ID=27177904

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212807D CH212807A (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) CH212807A (en)

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