CH161486A - Process for the production of a new dye. - Google Patents

Process for the production of a new dye.

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Publication number
CH161486A
CH161486A CH161486DA CH161486A CH 161486 A CH161486 A CH 161486A CH 161486D A CH161486D A CH 161486DA CH 161486 A CH161486 A CH 161486A
Authority
CH
Switzerland
Prior art keywords
amino
mol
oxynaphthalene
cyanuric chloride
acid
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 CH161486A publication Critical patent/CH161486A/en

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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
    • 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
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

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

Description

  

  Zusatzpatent zum Hauptpatent     Nr.   <B>159668.</B>    Verfahren zur Herstellung eines neuen Farbstoffes.    Es wurde gefunden,     dass    man einen neuen  Farbstoff erhält, wenn man<B>1</B>     Mol    des     di-          azotierten    Kupplungsproduktes aus einem       o-Ester    der     1-Diazo-8-oxynaphthalin-3,6-di-          sulfonsäure    mit     3-Amii)o-4-kresolmethyläther,     <B>1</B>     Mol        Cyanurchlorid,   <B>1</B>     Mol        1-Amino-8-oxy-          iiaphthaliii-3,

  6-disulfonsäure,   <B>1</B>     Mol        4-Amino-          4'-oxyazobenzol-3'-carbonsäure    und<B>1</B>     Mol          Monomethylanilin    derart aufeinander einwir  ken     lässt,        dass    das     diazotierte    Kupplungspro  dukt in der     7-Stellung    der     1-Amino-8-oxy-          napb,thalin-3,

  6-disulfoiisäure    kuppelt und ein  Halogen des     Cyanurchlorides    mit der     Amino-          gruppe    der     1-Amino-8-oxynaphthalinsulfon-          säure,    ein Halogen des     Cya#urchlorides    mit  der     Aminogruppe    der     4-Amino-4'-oxyazo-          berizol-3'-carbonsätire    und das letzte Halogen  atom des     Cyanurchlorides    mit der     Iminogruppe     des     Monomethylanilins    sich umsetzt,

   und     dass     man das so erhaltene Produkt zwecks<B>Ab-</B>  spaltung der     Estergruppe    der Einwirkung  eines verseifenden Mittels unterwirft.    Der neue Farbstoff bildet ein dunkle  Pulver, das sich in Wasser mit blaugrüner  Farbe löst. Er erzeugt auf Baumwolle aus  Färbebädern, die mit weichen oder harten  Wassern hergestellt worden sind, grüne Töne,  die sich durch ihre hervorragende Lichtecht  heit auszeichnen.  



  <I>Beispiel:</I>  <B>62,1</B> Teile des durch Kupplung von<B>1</B>     Mol          diazotierter        1-Amirio-8-oxynaphthalin-4'-toluol-          sulforisäureester-3,6-distilfonsäure    und<B>1</B>     Mol          3-Amino-4-kresolmethyläther    erhaltenen     Farb-          stoff.es    werden     diazotiert    und in eine abge  kühlte     ammoniakalische    Lösung von<B>75,9</B>  Teilen des     ternären    Kondensationsproduktes  aus<B>1</B>     Mol        Cyanurchlorid,

     <B>1</B>     Mol        1,8-Amino-          iiaphthol-3,6-disulforisäure,   <B>1</B>     Mol        4-Amino-4'-          oxyazobenzol-S'-carbonsäure    und<B>1</B>     Mol        Mono-          methylanilin    eingetragen. Nach beendeter  Kupplung wird auf<B>85 0</B> angewärmt und bei  dieser Temperatur durch Zufügen von Natron-      lauge der     Toluolsulfonsäurerest    abgespalten.  Der Farbstoff wird mit     Natriumchlorid        ans-          gefäHt    und getrocknet.



  Additional patent to main patent no. <B> 159668. </B> Process for the production of a new dye. It has been found that a new dye is obtained if <B> 1 </B> mol of the diazotized coupling product from an o-ester of 1-diazo-8-oxynaphthalene-3,6-disulfonic acid with 3 -Amii) o-4-cresol methyl ether, <B> 1 </B> moles of cyanuric chloride, <B> 1 </B> moles of 1-amino-8-oxy- iiaphthaliii-3,

  6-disulfonic acid, <B> 1 </B> mol of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and <B> 1 </B> mol of monomethylaniline can act on one another in such a way that the diazotized coupling product in the 7-position of the 1-amino-8-oxy-napb, thalin-3,

  6-disulfoic acid couples and a halogen of cyanuric chloride with the amino group of 1-amino-8-oxynaphthalenesulfonic acid, a halogen of cyano-chloride with the amino group of 4-amino-4'-oxyazoberizole-3'-carboxylic acid and the last halogen atom of the cyanuric chloride reacts with the imino group of monomethylaniline,

   and that the product obtained in this way is subjected to the action of a saponifying agent in order to split off the ester group. The new dye forms a dark powder that dissolves in water with a blue-green color. On cotton from dye baths that have been made with soft or hard water, it produces green tones that are characterized by their excellent lightfastness.



  <I> Example: </I> <B> 62.1 </B> parts of the 1-aminio-8-oxynaphthalene-4'-toluenesulfuric acid ester-3 diazotized by coupling <B> 1 </B> mol , 6-distilfonic acid and <B> 1 </B> mol of 3-amino-4-cresolmethylether obtained dye are diazotized and poured into a cooled ammoniacal solution of <B> 75.9 </B> parts of the ternary Condensation product from <B> 1 </B> mol of cyanuric chloride,

     <B> 1 </B> mol of 1,8-amino-iiaphthol-3,6-disulforic acid, <B> 1 </B> mol of 4-amino-4'-oxyazobenzene-S'-carboxylic acid and <B> 1 </B> Mol monomethylaniline entered. After coupling has ended, the mixture is heated to 85 ° and the toluenesulfonic acid residue is split off at this temperature by adding sodium hydroxide solution. The dye is made up with sodium chloride and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Farbstoffes, dadurch gekennzeichnet, dass man <B>1</B> Mol des diazotierten Kupplungsproduktes aus einem o-Ester der 1-Diazo-8-oxynaph- thalin-3,6-disulfonsäure mit S-Amino-4-L-resol- methyläther, <B>1</B> Mol Cyanurchlorid, <B>1</B> Mol 1- Amüio-8-oxynaphthalin-3,6-disulfonsäure, PATENT CLAIM: Process for the preparation of a new dye, characterized in that <B> 1 </B> mol of the diazotized coupling product from an o-ester of 1-diazo-8-oxynaphthalene-3,6-disulfonic acid with S- Amino-4-L-resolmethyl ether, <B> 1 </B> mol of cyanuric chloride, <B> 1 </B> mol of 1- amino-8-oxynaphthalene-3,6-disulphonic acid, <B>1</B> Mol 4-Amino-4'-oxyazobenzol-S'-carbonsäure und<B>1</B> Mol Monomethylanilin derart aufein ander einwirken lässt, dass das diazotierte Kupplungsprodukt in der 7-Stellung der 1- Amino-8-oxynaphthalin-3,6-disulfonsäure kup pelt und ein Halogen des Cyanurchlorides mit der Aminogruppe der 1-Amino-S-oxynaph- thalinsulfonsäure, <B> 1 </B> mol of 4-amino-4'-oxyazobenzene-S'-carboxylic acid and <B> 1 </B> mol of monomethylaniline can act on one another in such a way that the diazotized coupling product is in the 7-position of the 1 - Amino-8-oxynaphthalene-3,6-disulfonic acid kup pelt and a halogen of the cyanuric chloride with the amino group of 1-amino-S-oxynaphthalene sulfonic acid, ein Halogen des Cyanur- chlorides mit der Aminogruppe der 4-Amitio- 4'-oxyazobenzol-3'-carbonsäure und das letzte Halogenatom des Cyanurchlorides mit der Iminogruppe des Monomethylanilins sich um setzt und dass man das so erhaltene Produkt zwecks Abspaltung der Estergruppe der Ein wirkung eines verseifenden Mittels unterwirft. Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit blaugrüner Farbe löst. a halogen of cyanuric chloride with the amino group of 4-amitio-4'-oxyazobenzene-3'-carboxylic acid and the last halogen atom of cyanuric chloride with the imino group of monomethylaniline and that the product obtained in this way for the purpose of splitting off the ester group of the one subject to the action of a saponifying agent. The new dye forms a dark powder that dissolves in water with a blue-green color. Er erzeugt auf Baumwolle aus Färbebädern, die mit weichen oder harten Wassern hergestellt worden sind, grüne Töne, die sich durch ihre hervorragende Lichtecht heit auszeichnen. On cotton from dye baths that have been made with soft or hard water, it produces green tones that are characterized by their excellent lightfastness.
CH161486D 1931-12-17 1931-12-17 Process for the production of a new dye. CH161486A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH161486T 1931-12-17
CH159668T 1931-12-17
CH161488T 1931-12-17

Publications (1)

Publication Number Publication Date
CH161486A true CH161486A (en) 1933-04-30

Family

ID=27177413

Family Applications (1)

Application Number Title Priority Date Filing Date
CH161486D CH161486A (en) 1931-12-17 1931-12-17 Process for the production of a new dye.

Country Status (1)

Country Link
CH (1) CH161486A (en)

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