CH161487A - Process for the production of a new dye. - Google Patents

Process for the production of a new dye.

Info

Publication number
CH161487A
CH161487A CH161487DA CH161487A CH 161487 A CH161487 A CH 161487A CH 161487D A CH161487D A CH 161487DA CH 161487 A CH161487 A CH 161487A
Authority
CH
Switzerland
Prior art keywords
amino
mol
cyanuric chloride
acid
oxynaphthalene
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 CH161487A publication Critical patent/CH161487A/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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • C09B31/061—Disazo dyes from a coupling component "C" containing a directive hydroxyl group containing acid groups, e.g. -CO2H, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Description

  

  Verfahren zur Herstellung eines neuen Farbstoffes.    Es wurde gefunden, dass man einen neuen       Farbstoff    erhält, wenn mau 1     Mol.    des di  anotierten Kupplungsproduktes aus einem     o-          Ester    der     1-Diazo    - 8 -     oxynaphthalin    - 3,6 -     di-          sulfonsäure    mit     3-Amino-4-kresolmethyläther,     1     Mol.        Cyanurchlorid,    1     Mol.        1-Amino-8-oxy-          tiaphthalin-3,6-disulfonsäure,

      1     Mol.        4-Amino-          4'-        oxyazobenzol-    3'-     carbonsäure    und 1     Mol.     Ammoniak derart aufeinander einwirken lässt,  dass das dianotierte Kupplungsprodukt in der       7-Stellung    der     1-Amino-8-oxynaphthalin-3,6-          diNulfonsäure    kuppelt und ein Halogen des       Cyanurchlorides    mit der     Aminogruppe    der     1-          Amino-8-oxynaphthalitistilfonsäure,

      ein Halo  gen des     Cyanurchlorides    mit der     Aminogruppe     der     4-Amitio-4'-oxyazobenzol-3'-carbonsäui-e     und das letzte Halogenatom des     Cyanur-          chlorides    mit dein Ammoniak sich umsetzt,  und dass man das so erhaltene Produkt zwecks  Abspaltung der     Estergruppe    der Einwirkung  eines verseifenden Mittels unterwirft.  



  Der neue     Farbstoff    bildet ein dunkles  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>  62,1 Teile des durch Kupplung von 1     Mol.     dianotierter 1     -Amino    - 8 -     oxynaphthalin    -4'  toluolstilfonsäureester - 3,6     -disulfonsäure    und  1     Mol.        3-Amino-4-kresolmethyläther    erhaltenen  Farbstoffes werden dianotiert und in eine ab  gekühlte,     ammoniakalische    Lösung von 66,9  Teilen des     ternären    Kondensationsproduktes  aus 1     Mol.        Cyanurchlorid,    1     Mol.        1,8-Amino-          tiaphthol-3,6-disulfonsäure,

      1     Mol.        4-Amino-          4'-oxyazobenzol-3'-carbonsäure    und 1     Mol.     Ammoniak eingetragen. Nach beendeter Kupp  lung wird auf 85   angewärmt und bei dieser  Temperatur durch Zufügen von Natronlauge  der     Toluolsulfonsäurerest    abgespalten. Der       Farbstoff    wird mit     Natriumchlorid    ausgefällt  und getrocknet.



  Process for the production of a new dye. It has been found that a new dye is obtained if 1 mole of the di-anotized coupling product from an o-ester of 1-diazo-8-oxynaphthalene-3,6-disulfonic acid with 3-amino-4-cresol methyl ether, 1 mol. Cyanuric chloride, 1 mol. 1-amino-8-oxy-tiaphthalene-3,6-disulfonic acid,

      Allow 1 mole of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mole of ammonia to act on one another in such a way that the dianotated coupling product couples in the 7-position of 1-amino-8-oxynaphthalene-3,6-diNulfonic acid and a halogen of cyanuric chloride with the amino group of 1-amino-8-oxynaphthalitistilfonic acid,

      a halogen of the cyanuric chloride with the amino group of the 4-Amitio-4'-oxyazobenzene-3'-carboxylic acid and the last halogen atom of the cyanuric chloride reacts with the ammonia, and that the product thus obtained for the purpose of cleavage of the ester group Subjected to the action of a saponifying agent.



  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> 62.1 parts of the 3,6-disulfonic acid obtained by coupling 1 mol of dianotated 1-amino-8-oxynaphthalene -4'-toluenesulfonic acid and 1 mol of 3-amino-4-cresol methyl ether Dyestuff are dianotized and poured into a cooled, ammoniacal solution of 66.9 parts of the ternary condensation product of 1 mol. Cyanuric chloride, 1 mol. 1,8-Aminotiaphthol-3,6-disulfonic acid,

      1 mol. 4-Amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mol. Ammonia entered. After coupling is complete, the mixture is warmed to 85 and at this temperature the toluenesulfonic acid residue is split off by adding sodium hydroxide solution. The dye is precipitated with sodium chloride and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Farbstoffes, dadurch gekennzeichnet, dass man 1 bZol. des dianotierten Kupplungsproduktes aus einem o-Ester der 1-Diazo-8-oxynaphtha- lin-3,6-disulfonsäure mit 3-Amino-4-kresol- methyläther, 1 Mol. Cyanurchlorid, 1 Mol. 1-Amino-8-oxynaphthalin-3,6 -disulfonsäure, PATENT CLAIM: Process for the production of a new dye, characterized in that 1 bZol. of the dianotated coupling product from an o-ester of 1-diazo-8-oxynaphthalin-3,6-disulfonic acid with 3-amino-4-cresol methyl ether, 1 mol. cyanuric chloride, 1 mol. 1-amino-8-oxynaphthalene -3,6 -disulfonic acid, 1 Mol. 4-Amino-4'-oxyazobenzol-3'-carborisäure und 1 Mol. Ammoniak derart aufeinander einwirken lässt, dass das dianotierte Kupplungs produkt in der 7-Stellung der 1-Amino-8- oxynaphthalin-3,6-disulfonsäure kuppelt und ein Halogen des Cyanurchlorides mit der Aminogruppe der 1-Amino-8-oxynaphthalin- sulfonsäure, 1 mol. 4-Amino-4'-oxyazobenzene-3'-carboric acid and 1 mol. Ammonia can act on one another in such a way that the dianotated coupling product is in the 7-position of the 1-amino-8-oxynaphthalene-3,6-disulfonic acid couples and a halogen of cyanuric chloride with the amino group of 1-amino-8-oxynaphthalene sulfonic acid, ein Halogen des Cyanurchlorides mit der Aminogruppe der 4-Amino-4'-ogyazo- benzol-3'-carbonsäure und das letzte Halogen atom des Cyanurchlorides mit dem Ammoniak sich umsetzt, und dass man das so erhaltene Produkt zwecks Abspaltung der Estergruppe der Einwirkung eines verseifenden Mittels unterwirft. Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit blaugrüner Farbe löst. Er erzeugt auf Baumwolle aus Färbe bädern, die mit weichen oder harten Wassern hergestellt worden sind, grüne Töne, die sich durch ihre hervorragende Lichtechtheit aus zeichnen. a halogen of the cyanuric chloride with the amino group of the 4-amino-4'-ogyazobenzene-3'-carboxylic acid and the last halogen atom of the cyanuric chloride reacts with the ammonia, and that the product thus obtained is reacted for the purpose of cleavage of the ester group saponifying agent. 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.
CH161487D 1931-12-17 1931-12-17 Process for the production of a new dye. CH161487A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH161488T 1931-12-17
CH161487T 1931-12-17
CH159668T 1931-12-17

Publications (1)

Publication Number Publication Date
CH161487A true CH161487A (en) 1933-04-30

Family

ID=27177414

Family Applications (1)

Application Number Title Priority Date Filing Date
CH161487D CH161487A (en) 1931-12-17 1931-12-17 Process for the production of a new dye.

Country Status (1)

Country Link
CH (1) CH161487A (en)

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