CH294951A - Process for the production of a vat dye. - Google Patents

Process for the production of a vat dye.

Info

Publication number
CH294951A
CH294951A CH294951DA CH294951A CH 294951 A CH294951 A CH 294951A CH 294951D A CH294951D A CH 294951DA CH 294951 A CH294951 A CH 294951A
Authority
CH
Switzerland
Prior art keywords
production
vat
chloro
dye
vat dye
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH294951A publication Critical patent/CH294951A/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
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid

Landscapes

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 289992.         Verfahren        zur        Herstellung   <B>eines</B>     Küpenfarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Küpenfarbstoff    gelangt,     wenn    man    zwei     Verbindungen    der Formeln  
EMI0001.0008     
    worin das eine X eine     NH2-Gruppe    und das  andere X ein Halogenatom bedeutet, mitein  ander kondensiert.  



  Der neue     Farbstoff    löst sich in konzen  trierter Schwefelsäure mit     braunoranger    Farbe       und    färbt Baumwolle aus bordeauxroter     Küpe     in reinen     grünstichig    gelben Tönen.  



  Beim vorliegenden Verfahren kann man  entweder ein     1-Halogen-6-fluoranthrachinon,          vorzugsweise        1-Chlor-6-fluoranthraehinon,oder          1-Amino-6-fluoranthrachinon    als den einen       Ausgangsstoff    verwenden. Als zweiter Aus  gangsstoff kommt     4'-Chlor-1,1'-diphenyl.-4-          earbonsäureamid    oder ein     4'-Chlor-1,1'-diphe-          nyl-4-carbonsäurehalogenid,    insbesondere das  Chlorid     dieser    Säure in Betracht.  



  Die gemäss vorliegendem Verfahren aus  zuführenden Kondensationen erfolgen zweck  mässig in einem hochsiedenden organischen       Lösungsmittel    wie Nitrobenzol oder     o-Dichlor-          benzol    und bei erhöhter Temperatur. Bei der    Kondensation der     1-Halogen-6-fluoranthra..          chinone    mit dem     4'-Chlor-diphenylcarbon-          säureamid    empfiehlt es sich, dem Reaktions  gemisch ein säurebindendes Mittel, z. B. Na  trium- oder     Kaliumcarbonat,    und ausserdem  ein Kupfersalz wie     Kupfer(I)acetat    oder  Kupfer (I)     bromid    zuzufügen.  



  <I>Beispiel:</I>  12 Teile     1.-Amino-6-fluoranthrachinon    und       7.4    Teile     4'-Chlor-1,1'-diphenyl-4-carbonsäure-          chlorid    werden 2 Stunden bei 125 bis 130   verrührt.. Nach dem Erkalten wird der in  gelben Nadeln     ausgefallene    Farbstoff abge  saugt, mit Nitrobenzol und kochendem Alko  hol gewaschen und getrocknet.



  <B> Additional patent </B> to main patent no. 289992. Process for the production of <B> a </B> vat dye. It has been found that a valuable vat dye is obtained by using two compounds of the formulas
EMI0001.0008
    wherein one X is an NH2 group and the other X is a halogen atom, condensed with one another.



  The new dye dissolves in concentrated sulfuric acid with a brown-orange color and dyes cotton from a burgundy vat in pure greenish yellow tones.



  In the present process, either a 1-halo-6-fluoroanthraquinone, preferably 1-chloro-6-fluoroanthraquinone, or 1-amino-6-fluoroanthraquinone can be used as the one starting material. A second starting material is 4'-chloro-1,1'-diphenyl.-4-carboxamide or a 4'-chloro-1,1'-diphenyl-4-carboxylic acid halide, in particular the chloride of this acid.



  The condensations fed in according to the present process are expediently carried out in a high-boiling organic solvent such as nitrobenzene or o-dichlorobenzene and at elevated temperature. In the condensation of the 1-halogen-6-fluoroanthra .. quinones with the 4'-chloro-diphenylcarboxylic acid amide, it is advisable to add an acid-binding agent to the reaction mixture, eg. B. sodium or potassium carbonate, and also a copper salt such as copper (I) acetate or copper (I) bromide to be added.



  <I> Example: </I> 12 parts of 1.-amino-6-fluoroanthraquinone and 7.4 parts of 4'-chloro-1,1'-diphenyl-4-carboxylic acid chloride are stirred for 2 hours at 125 to 130 When it cools, the dye which has precipitated out in yellow needles is filtered off with suction, washed with nitrobenzene and boiling alcohol and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man zwei Verbindungen der Formeln EMI0001.0043 worin das eine X eine NH2-Gruppe und das andere X ein Halogenatom bedeutet, mitein ander kondensiert. Der neue Farbstoff löst sieh in konzen trierter Schwefelsäure mit. braunoranger Farbe und färbt Baumwolle aus bordeauxroter Küpe in reinen grünstiehig gelben Tönen. UNTERANSPRÜCHE: 1. PATENT CLAIM: Process for the production of a vat dye, characterized in that two compounds of the formulas EMI0001.0043 wherein one X is an NH2 group and the other X is a halogen atom, condensed with one another. The new dye dissolves in concentrated sulfuric acid. Brown-orange color and dyes cotton from a burgundy vat in pure greenish yellow tones. SUBCLAIMS: 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man 4'-Chlor-1,1'- diphenyl-4-carbonsäurechlorid als Ausgangs stoff verwendet. '?. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, da.ss die Kondensation in einem hochsiedenden organischen Lösungs mittel durchgeführt wird. Process according to patent claim, characterized in that 4'-chloro-1,1'-diphenyl-4-carboxylic acid chloride is used as the starting material. '?. Process according to claim, characterized in that the condensation is carried out in a high-boiling organic solvent.
CH294951D 1951-07-10 1951-07-10 Process for the production of a vat dye. CH294951A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH289992T 1951-07-10
CH294951T 1951-07-10

Publications (1)

Publication Number Publication Date
CH294951A true CH294951A (en) 1953-11-30

Family

ID=25732923

Family Applications (1)

Application Number Title Priority Date Filing Date
CH294951D CH294951A (en) 1951-07-10 1951-07-10 Process for the production of a vat dye.

Country Status (1)

Country Link
CH (1) CH294951A (en)

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