CH308896A - Process for the preparation of an asymmetric indigoid dye. - Google Patents

Process for the preparation of an asymmetric indigoid dye.

Info

Publication number
CH308896A
CH308896A CH308896DA CH308896A CH 308896 A CH308896 A CH 308896A CH 308896D A CH308896D A CH 308896DA CH 308896 A CH308896 A CH 308896A
Authority
CH
Switzerland
Prior art keywords
formula
dye
asymmetric
remainder
preparation
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 CH308896A publication Critical patent/CH308896A/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
    • C09B7/00—Indigoid dyes
    • C09B7/06—Indone-thionapthene indigos
    • 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
    • C09B7/00—Indigoid dyes
    • C09B7/10—Bis-thionapthene indigos

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Description

       

  Verfahren zur Herstellung eines     asymmetrischen        indigoiden    Farbstoffes.    Es wurde gefunden, dass ein     asymmetri-          scher        indigoider        Küpenfarbstoff    hergestellt  werden kann, indem man eine den Rest der       Pormel     
EMI0001.0008     
    abgebende Verbindung mit einer den Rest der  Formel  
EMI0001.0009     
    abgebenden Verbindung     kondensiert.     Der neue Farbstoff der Formel  
EMI0001.0011     
    stellt ein braunviolettes Pulver dar und zeigt  in konzentrierter     Schwefelsäure    blauviolette  Färbung.

   Der Farbstoff ergibt nach dem übli  chen     Pottaschedruckverfahren    auf Baumwolle    dunkelbraune Töne von sehr guter Lichtecht  heit.  



  Als Verbindung, die den Rest der erst  genannten Formel abgibt, kann zweckmässig  das     5-Methoxy-6-chlor-3-oxythionaphthen    ver  wendet werden, und als Verbindung, die den  Rest der zweitgenannten Formel abgibt, kann  zweckmässig ein     Anil,    insbesondere das     2-(p-          Dimethylamino)-anil    des     4,5-Benzo-3-oxythio-          naphthens    zur Anwendung gelangen.  



  Die Kondensation kann nach den an sich  bekannten, in der     indigoiden    Chemie üblichen  Methoden, beispielsweise durch Zusammen  bringen der Komponenten     in.    einem indifferen  ten Lösungsmittel, wie Benzol und insbeson  dere Chlorbenzol, bei leicht erhöhter Tem  peratur herbeigeführt werden.  



       Beispiel:     28,5 Teile     5-Methoxy-6-chlor-3-oxythio-          naphthen    werden in 1000 Teilen     Chlorbenzol     gelöst und mit 44,0 Teilen     2-(p-Dimethyl-          amino)-anil    des     4,5-Benzo-3-oxythionaphthens     während einigen Stunden bei 80 bis 90  kon  densiert. Der in guter Ausbeute abgeschiedene  Farbstoff wird filtriert, mit Chlorbenzol und       Alkohol    ausgewaschen und getrocknet.



  Process for the preparation of an asymmetric indigoid dye. It has been found that an asymmetric indigoid vat dye can be made by adding one of the remainder of the formula
EMI0001.0008
    donating compound with a the remainder of the formula
EMI0001.0009
    condensing compound emitting. The new dye in the formula
EMI0001.0011
    represents a brown-violet powder and shows blue-violet coloration in concentrated sulfuric acid.

   The dye produces dark brown shades of very good lightfastness on cotton using the customary potash printing process.



  As a compound that gives off the remainder of the first-mentioned formula, 5-methoxy-6-chloro-3-oxythionaphthene can conveniently be used, and as a compound that gives off the remainder of the second-mentioned formula, an anil, in particular the 2nd - (p-Dimethylamino) -anil of 4,5-benzo-3-oxythio- naphthens are used.



  The condensation can be brought about by methods known per se and customary in indigoid chemistry, for example by bringing the components together in an indifferent solvent, such as benzene and in particular chlorobenzene, at a slightly elevated temperature.



       Example: 28.5 parts of 5-methoxy-6-chloro-3-oxythio naphthene are dissolved in 1000 parts of chlorobenzene and mixed with 44.0 parts of 2- (p-dimethylamino) anil of 4,5-benzo-3 -oxythionaphthens condenses at 80 to 90 for a few hours. The dyestuff which has separated out in good yield is filtered off, washed out with chlorobenzene and alcohol and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines asym metrischen indigoiden Farbstoffes, dadurch gekennzeichnet, dass man eine den Rest der Formel EMI0002.0001 abgebende Verbindung mit einer den Rest der Formel EMI0002.0002 abgebenden Verbindung kondensiert. Der neue Farbstoff der Formel EMI0002.0004 stellt ein braunviolettes Pulver dar und zeigt, in konzentrierter Seliwefelsäiire blauviolette Färbung. Der Farbstoff ergibt nach dem üblichen Pottaschedruckverfahren auf Baum wolle dunkelbraune Töne von sehr guter Licht echtheit. PATENT CLAIM: Process for the production of an asymmetrical indigoid dye, characterized in that one is the remainder of the formula EMI0002.0001 donating compound with a the remainder of the formula EMI0002.0002 condensing compound emitting. The new dye in the formula EMI0002.0004 represents a brown-violet powder and shows blue-violet coloration in concentrated seliulfuric acid. The dye produces dark brown shades of very good lightfastness using the customary potash printing process on cotton.
CH308896D 1951-08-23 1951-08-23 Process for the preparation of an asymmetric indigoid dye. CH308896A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH308896T 1951-08-23

Publications (1)

Publication Number Publication Date
CH308896A true CH308896A (en) 1955-08-15

Family

ID=4493622

Family Applications (1)

Application Number Title Priority Date Filing Date
CH308896D CH308896A (en) 1951-08-23 1951-08-23 Process for the preparation of an asymmetric indigoid dye.

Country Status (3)

Country Link
CH (1) CH308896A (en)
DE (1) DE1017304B (en)
FR (1) FR1061518A (en)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE582613C (en) * 1930-11-17 1933-08-17 Chem Ind Basel Process for the production of asymmetrical indigoid dyes
DE631655C (en) * 1933-06-09 1936-06-25 I G Farbenindustrie Akt Ges Process for the production of asymmetrical indigoid dyes
CH184196A (en) * 1934-02-10 1936-05-15 Ig Farbenindustrie Ag Process for the production of an indigoid vat dye.
DE637210C (en) * 1934-02-11 1936-10-23 I G Farbenindustrie Akt Ges Process for the production of indigoid dyes
DE663314C (en) * 1935-04-19 1938-08-03 I G Farbenindustrie Akt Ges Process for the production of indigoid dyes

Also Published As

Publication number Publication date
DE1017304B (en) 1957-10-10
FR1061518A (en) 1954-04-13

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