CH205426A - Process for the production of an indigoid vat dye. - Google Patents

Process for the production of an indigoid vat dye.

Info

Publication number
CH205426A
CH205426A CH205426DA CH205426A CH 205426 A CH205426 A CH 205426A CH 205426D A CH205426D A CH 205426DA CH 205426 A CH205426 A CH 205426A
Authority
CH
Switzerland
Prior art keywords
production
vat dye
methoxy
indigoid
chloro
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 CH205426A publication Critical patent/CH205426A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Description

  

      Zusatzpatent    zum Hauptpatent Nr. 203143.    Verfahren zur Herstellung eines     indigoiden        Nüpenfarbstoffes.       Es wurde gefunden, dass ein     indigoider          Küpenfarbstoff    hergestellt werden kann, wenn  man     5-Chlor-6-methoxy-2,1-naphtbthioindoxyl     mit     5,7-Dibromisatin    kondensiert.  



  Der erhaltene     indigoide        Küpenfarbstoff     der Formel  
EMI0001.0010     
    stellt ein     braunes    Pulver dar, das sich in  konzentrierter Schwefelsäure mit violetter  Farbe löst und Baumwolle aus gelb gefärbter       Küpe    in klaren braunen Tönen färbt.  



  Das     5-Chlor-6-metboxy-2,1-naphththioin-          doxyl    kann z. B. wie folgt hergestellt werden  Aus der     6-Methoxy-2-naphthalinsulfonsäure     wird durch Behandeln mit     Phosphorpenta-          chlorid    das 6-Methoxy-2-naphthalirisulfochlo-         rid    hergestellt und dieses wird im Reak  tionsgemisch durch Chlorieren mit     Sulfuryl-          chlorid    in das     5-Chlor-6-metboxy=2-naphtha-          linsulfochlorid    übergeführt, das aus Benzol  in farblosen Kristallen vom Schmelzpunkt  142   kristallisiert.

   Das erhaltene     Sulfochlorid     wird auf übliche Weise durch Reduktion und  nachfolgende Kondensation mit Monochlor  essigsäure in die     5-Chlor-6-methoxy-2-naph-          thalinthioglykolsäure    vom Schmelzpunkt 157  bis 158   übergeführt. Aus dieser     Thiogly-          kolsäure    entsteht durch Umsetzen mit     Pbos-          phortrichlorid    und Aluminiumchlorid das aus       o-Dichlorbenzol    in Nadeln kristallisierende       5-Chlor-6-methoxy-2,1-naphththioindoxyl    vom  Schmelzpunkt<B>265-2660.</B>  



  Die     Kondensation    kann in Gegenwart  von Lösungsmitteln, wie z. B. Alkohol, Eis  essig, Benzol, Chlorbenzol oder     Tetrachlor-          äthan    erfolgen.  



  <I>Beispiel:</I>  264,5 Teile     5-Chlor-6-methoxy-2,1-naphth-          thioindoxyl    und 305 Teile     5,7-Dibromisatin         werden in 6000 Teilen Eisessig erhitzt, bis  die Kondensation beendigt ist. Hierauf wird  filtriert, mit Eisessig sowie Alkohol gewa  schen und getrocknet.



      Additional patent to main patent no. 203143. Process for the production of an indigoid pimple dye. It has been found that an indigoid vat dye can be produced by condensing 5-chloro-6-methoxy-2,1-naphthobthioindoxyl with 5,7-dibromoisatin.



  The indigoid vat dye obtained of the formula
EMI0001.0010
    is a brown powder that dissolves in concentrated sulfuric acid with a violet color and dyes cotton from a yellow vat in clear brown tones.



  The 5-chloro-6-metboxy-2,1-naphththioin- doxyl can, for. B. be prepared as follows From the 6-methoxy-2-naphthalenesulfonic acid, the 6-methoxy-2-naphthalenesulfochloride is prepared by treatment with phosphorus pentachloride and this is in the reaction mixture by chlorination with sulfuryl chloride into 5-chlorine -6-metboxy = 2-naphthalene sulfochloride, which crystallizes from benzene in colorless crystals with a melting point of 142.

   The sulfochloride obtained is converted into 5-chloro-6-methoxy-2-naphthalene thioglycolic acid with a melting point of 157 to 158 in the customary manner by reduction and subsequent condensation with monochloroacetic acid. This thioglycolic acid is converted into 5-chloro-6-methoxy-2,1-naphthioindoxyl with a melting point of <B> 265-2660. </B>, which crystallizes from o-dichlorobenzene in needles by reaction with phosphorus trichloride and aluminum chloride



  The condensation can be carried out in the presence of solvents, such as. B. alcohol, glacial acetic acid, benzene, chlorobenzene or tetrachloroethane.



  <I> Example: </I> 264.5 parts of 5-chloro-6-methoxy-2,1-naphth-thioindoxyl and 305 parts of 5,7-dibromoisatin are heated in 6000 parts of glacial acetic acid until the condensation has ended. It is then filtered, washed with glacial acetic acid and alcohol and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines indigo- iden güpenfarbstoffes, dadurch gekennzeich net, dass mau 5-Chlor-6-methoxy-2,1-naphth- thioindoxyl mit 5,7-Dibromisatin kondensiert. Der erhaltene indigoide Küpenfarbstoff der Formel EMI0002.0010 stellt ein braunes Pulver dar, das sich in konzentrierter Schwefelsäure mit violetter Farbe löst und Baumwolle aus gelb gefärbter Küpe in klaren braunen Tönen färbt. PATENT CLAIM: A process for the production of an indigo-id güpen dyestuff, characterized in that 5-chloro-6-methoxy-2,1-naphthioindoxyl is condensed with 5,7-dibromoisatin. The indigoid vat dye obtained of the formula EMI0002.0010 is a brown powder that dissolves in concentrated sulfuric acid with a violet color and dyes cotton from a yellow vat in clear brown tones.
CH205426D 1937-10-22 1937-10-22 Process for the production of an indigoid vat dye. CH205426A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH205426T 1937-10-22
CH203143T 1937-10-22

Publications (1)

Publication Number Publication Date
CH205426A true CH205426A (en) 1939-06-15

Family

ID=25723900

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205426D CH205426A (en) 1937-10-22 1937-10-22 Process for the production of an indigoid vat dye.

Country Status (1)

Country Link
CH (1) CH205426A (en)

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