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CH132803A - Process for the preparation of a stain dye. - Google Patents

Process for the preparation of a stain dye.

Info

Publication number
CH132803A
CH132803A CH132803DA CH132803A CH 132803 A CH132803 A CH 132803A CH 132803D A CH132803D A CH 132803DA CH 132803 A CH132803 A CH 132803A
Authority
CH
Switzerland
Prior art keywords
dye
acid
meta
water
brownish
Prior art date
Application number
Other languages
German (de)
Inventor
Durand Huguenin S A
Original Assignee
Durand & Huguenin Sa
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 Durand & Huguenin Sa filed Critical Durand & Huguenin Sa
Publication of CH132803A publication Critical patent/CH132803A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/38Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
    • C09B45/40Chromium compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02Disazo dyes
    • C09B31/06Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • C09B31/061Disazo dyes from a coupling component "C" containing a directive hydroxyl group containing acid groups, e.g. -CO2H, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02Disazo dyes
    • C09B35/039Disazo dyes characterised by the tetrazo component
    • C09B35/04Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/08Preparation of azo dyes from other azo compounds by reduction
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/44Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Coloring (AREA)

Description

  

      1-          Verfahren    zur Darstellung eines     Beizenfarbstoffes.       Im Hauptpatent wurde ein Verfahren     be-          wonach    ein wertvoller     Beizen-          farbstoff    erhalten wird, indem     man    in     p-Ainino-          0-Stilfobenzolazosalicylsä(ire    die     Aminogruppe          diazotiert    und mit     Saliey1säure    kuppelt.  



  Es wurde nun gefunden,     dass    ein ähnlicher  Farbstoff erhalten wird, wenn man im     Mono-          ,        a7        ,ofarbstoff        p-Amino-o-sulfoberi7,olazo-i-neta-          kresotinsäure    die     Aminogruppe        diazotiert    und  mit     irieta-1Zi-esotinsätire    kuppelt.

         p-Ainino-o-sulfoberizolazo-meta-kresotiii-          säure    kann auf verschiedenen Wegen erhalten  werden, zum Beispiel:  <B>1.</B>     -Mionoacetyl-p-phenylendiainiiisulfosäure     wird     diazotiert    und mit     meta-Kresotinsäure     gekuppelt. Im erhaltenen     Azofarbstoff    wird  die     Acetylgruppe    durch Verseifen eliminiert  und die freie     Aminogruppe    gebildet.  



  2.     p-Nitraiiilin-o-sulfosäure    wird     diazotiert          und    in bekannter Weise mit     meta-Kresotin-          gäure    gekuppelt.     Irn    erhaltenen     Monoazofarb-          stoff    wird die Nitrogruppe zur     Aminogruppe     reduziert.    <B>3.</B>     p-Phonylendiaminsulfosäure    wird     diazo-          tiert    und mit     ineta-Kresotinsäure    gekuppelt.  



  Der auf die eine oder andere Weise er  haltene Körper wird weiter     diazotiert        und     mit     nieta-Ki-esotinsäure    gekuppelt. Immer  wird der gleiche Endfarbstoff erhalten.  



  Das Verfahren wird erläutert durch folgen  des Beispiel:  <B>351</B> Teile     p-Amino-o-sulfobenzolazo-meta-          kresotinsäure    werden in Form einer feinen  wässerigen Suspension unter Kühlen mit<B>30</B>  Teilen Salzsäure versetzt und durch langsames  Zugeben von<B>7</B> Teilen     Natriumnitrit        diazotiert.     Der<B>-</B>schwer lösliche rotbraun gefärbte     Diazo-          körper    wird     abfiltriert    und in feuchtem Zu  stande allmählich bei<B>0-5'</B>     C    in eine Mi  schung von<B>170</B> Teilen     meta-Kresotinsäure,     <B>1000</B> Teilen Wasser,

   40 Teilen     Ätznatron     und<B>500</B> Teilen     Magnesiumkarbonat    einge  rührt. Die Kupplungsmasse, die zu Anfang  eine braunschwarze Färbung zeigt, wird nach  einiger Zeit gelbbraun. Nach beendigter<B>Kupp-</B>  lung wird die Masse angesäuert und filtriert.  Der so ausgeschiedene Farbstoff wird in      Wasser und Borax heiss gelöst,     filtriert,    even  tuell nochmals sauer abgeschieden Lind her  nach wieder in Wasser und Borax     gelöRt     und mit Kochsalz     ausgesalzen.     



  In diesem Beispiel kann die Kupplung  mit auch Hilfe von Soda oder     Natronlatige     durchgeführt werden.  



  In Wasser löst sich der neue Farbstoff  mit braungelber Farbe, die auf Zusatz von  Natronlauge nach rotviolett umschlägt. In  konzentrierter Schwefelsäure löst er sich     init     blauer Farbe. Durch Verdünnen dieser Lö  sung mit Wasser wird er als dunkelbraune  Flocken gefällt.  



  Der neue Farbstoff färbt     ehromierte    Wolle  in     braunstichig    orangen Tönen an. Mit Chrom  beize auf Baumwolle gedruckt gibt er kräftige       braunstichig    orange Nuancen, die     rotstichis          ger    sind als diejenigen des Farbstoffes     de-          Hauptpatentes    und gute Echtheitseigenschaf  ten aufweisen.



      1- Process for the preparation of a stain dye. The main patent describes a process whereby a valuable mordant dye is obtained by diazotizing the amino group in p-amino-0-stilfobenzolazosalicylic acid and coupling it with salyic acid.



  It has now been found that a similar dye is obtained if the amino group in the mono-, a7, o-dye is diazotized with p-amino-o-sulfoberi7, olazo-i-netakresotinic acid and coupled with irieta-1Zi-esotinsätire.

         p-Ainino-o-sulfoberizolazo-meta-cresotinic acid can be obtained in various ways, for example: 1. -Mionoacetyl-p-phenylenediamine-sulfonic acid is diazotized and coupled with meta-cresotinic acid. In the azo dye obtained, the acetyl group is eliminated by saponification and the free amino group is formed.



  2. p-nitrilin-o-sulfonic acid is diazotized and coupled with meta-cresotinic acid in a known manner. In the monoazo dye obtained, the nitro group is reduced to the amino group. <B> 3. </B> p-Phonylenediaminesulfonic acid is diazo- tated and coupled with ineta-cresotinic acid.



  The body retained in one way or another is further diazotized and coupled with nieta-ki-esotinic acid. The same final dye is always obtained.



  The process is illustrated by the following example: <B> 351 </B> parts of p-amino-o-sulfobenzolazo-metacresotinic acid are mixed with <B> 30 </B> parts of hydrochloric acid in the form of a fine aqueous suspension while cooling and diazotized by slowly adding <B> 7 </B> parts of sodium nitrite. The <B> - </B> poorly soluble, red-brown colored diazo body is filtered off and, in the moist state, gradually at <B> 0-5 '</B> C into a mixture of <B> 170 </B> Parts meta-cresotinic acid, <B> 1000 </B> parts of water,

   40 parts of caustic soda and <B> 500 </B> parts of magnesium carbonate are stirred in. The coupling compound, which initially shows a brown-black color, turns yellow-brown after a while. After the <B> coupling </B> process is complete, the mass is acidified and filtered. The dyestuff separated out in this way is dissolved in hot water and borax, filtered, possibly again separated in acidic form and then redissolved in water and borax and salted out with common salt.



  In this example the coupling can also be carried out with the help of soda or soda soda.



  The new dye dissolves in water with a brownish-yellow color, which changes to red-violet when caustic soda is added. In concentrated sulfuric acid it dissolves in a blue color. By diluting this solution with water, it is precipitated as dark brown flakes.



  The new dye dyes honored wool in brownish orange tones. Printed with chrome stain on cotton, it gives strong brownish orange nuances, which are more reddish than those of the dye of the main patent and have good fastness properties.

 

Claims (1)

PATEN'rAXSPUüCll: Verfahren zur Darstellung eines Beizen- larbstoffes, dadurch gekennzeichnet, dass man in p-Amirio-o-stilfobenzolazo-meta-kresotin- säure die freie Amitiogruppe diazotiert und mit meta-Kresotinsäure kuppelt. In Wasser löst sich der neue Farbstoff mit braungelber Farbe, die auf Zusatz von Natronlauge nach rotviolett umschlägt. In konzentrierter Schwefelsäure last er sichmit blauer Farbe. PATEN'rAXSPUüCll: Process for the preparation of a pickling agent, characterized in that the free amino group in p-Amirio-o-stilfobenzolazo-meta-cresotinic acid is diazotized and coupled with meta-cresotinic acid. The new dye dissolves in water with a brownish-yellow color, which changes to red-violet when caustic soda is added. In concentrated sulfuric acid it looks blue. Durch Verdünnen dieser Lb- sung mit Wasser wird er als dunkelbraune Flocken gefällt. Der neue Farbstoff färbt chromierte Wolle in braunstichig orangen Tönen an. Mit Chrombeize auf Baumwolle gedruckt gibt er kräftigebraunstichigorange Nuancen, die rotstichiger sind als diejenigen des Farbstoffes des Hauptpatentes und gute Echtheitseigenschaften aufweisen. By diluting this solution with water it is precipitated as dark brown flakes. The new dye stains chromed wool in brownish orange tones. Printed with chrome stain on cotton, it gives strong brownish orange nuances that are more reddish than those of the dye of the main patent and have good fastness properties.
CH132803D 1928-01-12 1928-01-12 Process for the preparation of a stain dye. CH132803A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH132803T 1928-01-12
CH123930T 1928-01-12

Publications (1)

Publication Number Publication Date
CH132803A true CH132803A (en) 1929-04-30

Family

ID=25710165

Family Applications (1)

Application Number Title Priority Date Filing Date
CH132803D CH132803A (en) 1928-01-12 1928-01-12 Process for the preparation of a stain dye.

Country Status (1)

Country Link
CH (1) CH132803A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0158888A3 (en) * 1984-04-05 1987-02-04 Hoechst Aktiengesellschaft Disazo compounds, process for their preparation and their use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0158888A3 (en) * 1984-04-05 1987-02-04 Hoechst Aktiengesellschaft Disazo compounds, process for their preparation and their use

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