CH228851A - Process for the production of a new anthraquinone dye. - Google Patents

Process for the production of a new anthraquinone dye.

Info

Publication number
CH228851A
CH228851A CH228851DA CH228851A CH 228851 A CH228851 A CH 228851A CH 228851D A CH228851D A CH 228851DA CH 228851 A CH228851 A CH 228851A
Authority
CH
Switzerland
Prior art keywords
sulfuric acid
dimethyl
blue
propylaminoanthraquinone
oxy
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH228851A publication Critical patent/CH228851A/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
    • C09B1/285—Dyes with no other substituents than the amino groups

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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 neuen     Anthrachinonfarbstof%s.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung eines neuen     An-          thraehinonfarbstoffes,    nämlich des     _1-y-Oxy-          a,ss-        dimethyl    - n -     propylamino-4-y-sulf        ato-a,ss-          dimethyl-n-propylaminoanthrachinons.     



       Erfindungsgemäss    wird das     1-y-Oxy-a,ss-          dimethyl-n-propylamino    -<I>4 - y</I> -     sulf        ato   <I>-</I>     a,ss-        di-          methyl-n-propylaminoanthrachinon    dadurch       erhalten,    dass man     1,4-Di-y-oxy-a,ss-dimethyl-          n-propylaminoanthrachinon    mit einem     Sul-          furierungsmittel    bis zur Einführung einer       Schwefelsäureestergruppe    umsetzt.  



  Als     Sulf        urierungsmittel    eignen sich Schwe  felsäure und     Natriumpyrosulfat.     



  Der erzielte Farbstoff ist blau. Er löst  sich in Wasser mit heller, blauer Färbung  und in 100%iger Schwefelsäure mit rosa Fär  bung, die durch Zugabe von Formaldehyd  blau wird. Er färbt Wolle aus saurem Bad  in gleichmässigen, blauen     Farbtönen    von guter  Lichtechtheit.    Die vorliegende Erfindung wird durch  die nachstehenden Beispiele erläutert, ohne  darauf beschränkt zu sein. Die Teile bedeu  ten Gewichtsteile.

      <I>Beispiel 1:</I>  10 Teile     1,4-Di-y-oxy-a,ss-dimethyl-n-pro-          pylaminoanthrachinon    (hergestellt durch Um  setzung von 1     Mol.        Leukochinizarin    mit  2     Mol.        3-Amino-2-methylbutanol    und Oxyda  tion des Produktes) werden bei 0  C in  100 Teilen 83 %     iger    Schwefelsäure gelöst und  so lange mit 98 %     iger    Schwefelsäure versetzt,  bis eine Probe in verdünnter wässriger Na  triumcarbonatlösung löslich ist.

   Das     Sulfu-          rierungsgemisch    wird dann in ein     Eis-Was-          ser-Gemisch    gegossen, filtriert und der Rück  stand in verdünnter     Natriumhydroxydlösung     gelöst, von unlöslichen Bestandteilen durch  Filtrieren befreit,     ausgesalzen    und getrock  net.

             Beispiel   <I>2:</I>  6 Teile     1,4-Di-y-oxy-a,ss-dimethyl-n-pro-          pylaminoanthrachinon,    6 Teile     Natriumpyro-          sulfat        und    40 Teile     Pyridin    werden zusam  men während     11/a    Stunden bei ca.<B>60'C</B> ge  rührt und das     Pyridin    hierauf, nach Zugabe  von     Natriumcarbonat,    mit Wasserdampf ab  destilliert.

   Die erhaltene blaue,     wässrige    Lö  sung wird von unlöslichen Bestandteilen  durch Filtrieren befreit und der Farbstoff  mittels     Natriumchlorid    ausgefällt,     abfiltiert     und getrocknet.



  Process for the preparation of a new anthraquinone dye% s. The present invention relates to a process for the production of a new anthraquinone dye, namely the _1-y-oxy- a, ss- dimethyl-n-propylamino-4-y-sulfato-a, ss- dimethyl-n-propylaminoanthraquinone.



       According to the invention, the 1-y-oxy-a, ss- dimethyl-n-propylamino - <I> 4 - y </I> - sulf ato <I> - </I> a, ss- dimethyl-n- Propylaminoanthraquinone obtained by reacting 1,4-di-y-oxy-α, β-dimethyl-n-propylaminoanthraquinone with a sulphurating agent until a sulfuric acid ester group is introduced.



  Sulfurizing agents are sulfuric acid and sodium pyrosulfate.



  The dye obtained is blue. It dissolves in water with a light blue color and in 100% sulfuric acid with a pink color, which turns blue when formaldehyde is added. It dyes wool from an acid bath in even, blue shades of good lightfastness. The present invention is illustrated by the following examples without being restricted thereto. The parts mean parts by weight.

      <I> Example 1: </I> 10 parts of 1,4-di-y-oxy-a, ss-dimethyl-n-propylaminoanthraquinone (prepared by reacting 1 mol. Of leucoquinizarin with 2 mol. 3-amino -2-methylbutanol and Oxyda tion of the product) are dissolved at 0 C in 100 parts of 83% sulfuric acid and treated with 98% sulfuric acid until a sample is soluble in dilute aqueous sodium carbonate solution.

   The sulfurization mixture is then poured into an ice-water mixture, filtered and the residue dissolved in dilute sodium hydroxide solution, freed from insoluble constituents by filtration, salted out and dried.

             Example <I> 2: </I> 6 parts of 1,4-di-y-oxy-a, ss-dimethyl-n-propylaminoanthraquinone, 6 parts of sodium pyrosulfate and 40 parts of pyridine are used together during 11 / a Stirred for hours at approx. 60.degree. C. and the pyridine then, after adding sodium carbonate, distilled off with steam.

   The blue, aqueous solution obtained is freed from insoluble components by filtration and the dye is precipitated using sodium chloride, filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Anthrachinonfarbstoffes, nämlich des 1-y- Oxy-a,ss-dimethyl-n-propylamino,- 4-y-sulf ato- a,ss-dimethyl-n-propylaminoanthrachinons, da durch gekennzeichnet, dass 1,4-Di-y-oxy-a,ss- dimethyl - n - propylaminoanthrachinon mit einem Sulfurierungsmittel bis zur Einführung einer Schwefelsäureestergruppe umgesetzt wird. Der neue Farbstoff ist blau. PATENT CLAIM: Process for the production of a new anthraquinone dye, namely the 1-y-oxy-a, ss-dimethyl-n-propylamino, - 4-y-sulf ato-a, ss-dimethyl-n-propylaminoanthraquinone, as characterized in that 1,4-Di-y-oxy-a, ss-dimethyl-n-propylaminoanthraquinone is reacted with a sulfurizing agent until a sulfuric acid ester group is introduced. The new dye is blue. Er löst sich in Wasser mit heller, blauer Färbung und in 100%iger Schwefelsäure mit rosa Färbung, die dureh Zugabe von Formaldehyd blau wird. Er färbt Wolle aus saurem Bad in gleichmässigen, blauen Farbtönen von guter Lichtechtheit. UNTERANSPRVCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass die Einführung der Schwefelsäureestergruppe durch Schwe felsäure erfolgt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass die Einführung der Schwefelsäureestergruppe durch Natrium- pyrosulfat erfolgt. It dissolves in water with a light, blue color and in 100% sulfuric acid with a pink color, which turns blue with the addition of formaldehyde. It dyes wool from an acid bath in even, blue shades of good lightfastness. SUBClaims: 1. Method according to claim, characterized in that the sulfuric acid ester group is introduced by sulfuric acid. 2. The method according to claim, characterized in that the sulfuric acid ester group is introduced by sodium pyrosulfate.
CH228851D 1940-10-08 1941-10-07 Process for the production of a new anthraquinone dye. CH228851A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB228851X 1940-10-08
CH225783T 1941-10-07

Publications (1)

Publication Number Publication Date
CH228851A true CH228851A (en) 1943-09-15

Family

ID=25726935

Family Applications (1)

Application Number Title Priority Date Filing Date
CH228851D CH228851A (en) 1940-10-08 1941-10-07 Process for the production of a new anthraquinone dye.

Country Status (1)

Country Link
CH (1) CH228851A (en)

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