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CH191167A - Process for the production of a new dye of the anthraquinone series. - Google Patents

Process for the production of a new dye of the anthraquinone series.

Info

Publication number
CH191167A
CH191167A CH191167DA CH191167A CH 191167 A CH191167 A CH 191167A CH 191167D A CH191167D A CH 191167DA CH 191167 A CH191167 A CH 191167A
Authority
CH
Switzerland
Prior art keywords
anthraquinone
production
dye
new dye
anthraquinone series
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH191167A publication Critical patent/CH191167A/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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/36—Amino acridones

Landscapes

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

Description

  

      Zusatzpatent    zum Hauptpatent Nr. 189142.    Verfahren zur Herstellung eines neuen     Farbstoffes    der     Anthraehinonreihe.       Es wurde gefunden, dass man einen neuen  Farbstoff der     Anthrachinonreihe    = das     4-          Benzoylamino    -     1-a-naphthanthrachinonakri-          don    - erhält, wenn man bei     1-(al-Naphth,-#-1-          amina-ss,-        carbonsäureäthylester)

  -4-.benzoyl-          amino-anthrachinon    den     Ringsohluss    zum       Acridon    vornimmt durch     Behandeln    des       Esters    mit alkalischen     Reduktionsmitteln.     Der so erhaltene     Farbstoff    ist ein dunkles  Pulver, das Baumwolle aus     violettroter        Küpe          grünstichig    grau anfärbt. Die     Schwefel-          siiurelösung        ist    orange, in Wasser gegossen  ergeben sich grüngraue Flocken.

           Beispiel:       10 Gewichtsteile nass .gemahlenes 1-(a,  Naphthylamino-     ss,    -     carbonsäureäthylester)-4-          benzoylamino-anthrachinon    werden in 600       Gewichtsteilen    Wasser mit 30     Gewichtsteilen     30 %     iger        Natriumhydroxydlösung    und 1.5 Ge  wichtsteilen     Natriumhydrosulfit    1 Stunde bei  65 bis<B>70'</B>     verküpt,    dann filtriert,     oxydiert            unter        Einblasen    von     Luft,    abgesaugt,

       heiss     neutral gewaschen     und    getrocknet.  



  Das     1-(a,-Naphthylamino-ssl-ca.rbonsäure-          äthylester)    - 4 -     benzoylamino    -     anthrachinon     kann     wie    folgt     hergestellt        werden     34,2 Gewichtsteile     1-Amino-4-benzoyl-          amino-anthrachinon,        23,4    Gewichtsteile     1-          Chlornaphthalin-2-carbonsäureäthylester,    1.2  Gewichtsteile Natriumkarbonat und 0,6 Ge  wichtsteile wasserfreies Kupferchlorid wer  den in 240 Gewichtsteilen     Nitrobenzol    20  Stunden lang rückfliessend gekocht.

       Nach     dem Erkalten wird abgesaugt,     mit    wenig  Nitrobenzol, dann     Toluol    und Alkohol und  zuletzt mit     Wasser    .gewaschen, mit Salzsäure  gedeckt, neutral gewaschen und getrocknet.



      Additional patent to the main patent No. 189142. Process for the production of a new dye of the anthraehinone series. It has been found that a new dye of the anthraquinone series = 4-benzoylamino - 1-a-naphthanthraquinone acridone - is obtained when 1- (al-naphth, - # - 1- amina-ss, - carboxylic acid ethyl ester)

  -4-.benzoyl-amino-anthraquinone makes the ring base to the acridone by treating the ester with alkaline reducing agents. The dye thus obtained is a dark powder which dyes cotton from a violet-red vat with a greenish gray. The sulfuric acid solution is orange, poured into water gives green-gray flakes.

           Example: 10 parts by weight of wet ground 1- (a, naphthylamino- ss, - carboxylic acid ethyl ester) -4- benzoylamino-anthraquinone are mixed in 600 parts by weight of water with 30 parts by weight of 30% sodium hydroxide solution and 1.5 parts by weight of sodium hydrosulfite for 1 hour at 65 to <B> 70 '</B> vat, then filtered, oxidized while blowing in air, sucked off,

       washed hot, neutral and dried.



  The 1- (a, -naphthylamino-ssl-ca.rboxylic acid ethyl ester) -4-benzoylamino-anthraquinone can be prepared as follows: 34.2 parts by weight of 1-amino-4-benzoylamino-anthraquinone, 23.4 parts by weight of 1- Ethyl chloronaphthalene-2-carboxylate, 1.2 parts by weight of sodium carbonate and 0.6 parts by weight of anhydrous copper chloride who refluxed for 20 hours in 240 parts by weight of nitrobenzene.

       After cooling, it is filtered off with suction, washed with a little nitrobenzene, then toluene and alcohol and finally with water, covered with hydrochloric acid, washed neutral and dried.

Claims (1)

PATENTANSPRUCH: Zierfahren zur Herstellung eines neuen Farbstoffes der Anthrachinonreihe -,das 4 Ben:zoylamino-1-a-naphthanthrachinonakri don -, dadurch gekennzeichnet, dass man bei 1- (al-Naphthylamino-ssl-carbonsäureäthyl- ester)-4-benzoylamino-anthrachinon den Ring- schluB zum Acridon vornimmt durch Behan deln des Esters mit alkalischen Reduktions- mitteln. Der so erhaltene Farbstoff ist ein dunkles Pulver, PATENT CLAIM: Decorative process for the production of a new dye of the anthraquinone series - the 4 Ben: zoylamino-1-a-naphthanthraquinone acrid -, characterized in that 1- (al-naphthylamino-ssl-carboxylic acid ethyl ester) -4-benzoylamino- anthraquinone closes the ring to acridone by treating the ester with alkaline reducing agents. The dye thus obtained is a dark powder, das Baumwolle aus violett- roter Küpe grünstichig brau anfärbt. Die Schwefelsäurelösung ist orange, in Wasser gegossen ergeben sich grüngraue Flocken. the cotton from the violet-red vat dyes a greenish brown. The sulfuric acid solution is orange, poured into water results in green-gray flakes.
CH191167D 1936-01-10 1936-01-10 Process for the production of a new dye of the anthraquinone series. CH191167A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH189142T 1936-01-10
CH191167T 1936-01-10

Publications (1)

Publication Number Publication Date
CH191167A true CH191167A (en) 1937-05-31

Family

ID=25721757

Family Applications (1)

Application Number Title Priority Date Filing Date
CH191167D CH191167A (en) 1936-01-10 1936-01-10 Process for the production of a new dye of the anthraquinone series.

Country Status (1)

Country Link
CH (1) CH191167A (en)

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