CH161485A - Process for the production of a new dye. - Google Patents

Process for the production of a new dye.

Info

Publication number
CH161485A
CH161485A CH161485DA CH161485A CH 161485 A CH161485 A CH 161485A CH 161485D A CH161485D A CH 161485DA CH 161485 A CH161485 A CH 161485A
Authority
CH
Switzerland
Prior art keywords
amino
mol
cyanuric chloride
acid
halogen
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 CH161485A publication Critical patent/CH161485A/en

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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
    • 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
    • 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

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

Description

  

  Verfahren zur Herstellung eines     neuen        Farbstoffes.       Es wurde gefunden, dass man einen neuen  Farbstoff erhält, wenn man 1     Mol    des     dia-          zotierten    Kupplungsproduktes aus einem     o-          Ester    der     1-Diazo-8-oxynaphthalin-3,6-disul-          fonsäure    mit     3-Arnino-4-kr,esolmethyläther,     1     Mol        Cyanurchlorid,    1     Mol        1-Amino-8-oxy-          rraphtbalin-3,6-disulforrsäure,

          1Mo1        4-Amino-          4'-oxyazobenzol-3'-carbonsäure    und 1     Mol          Monomethylamin    derart aufeinander einwirken  lässt, dass das     diazotierte    Kupplungsprodukt  in der     7-Stellung        derl-Anrino-8-oxynaphthalin-          3,6-disulfonsärrre    kuppelt und ein Halogen  des     Cyanurchlorides    mit     .der"Aminogruppe     der     1-Amino-8-oxynaphthalinsulfonsäure,

      ein  Halogen des     Cyanurchlorides    mit der     Amino-          gruppe    der     4-Amirro-4'-oxyazobenzol-3'-carbon-          säure    und das letzte Halogenatom des     Cya-          nurchlorides    mit der     Aminogruppe    des Mono  methylamins sich umsetzt und dass man das  so erhaltene Produkt zwecks Abspaltung der       Estergruppe    der Einwirkung eines     verseifen-          den    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          diazotierter        1-Amino-8-oxynaphthalin-4'-toluol-          sulfonsäureester-3,6-disulfonsäure    und 1     Mol          3-A'mino-4-kresolmethyläther    erhaltenen Farb  stoffes werden     diazotiert    und in eine abge  kühlte     ammoniakalische    Lösung von 68,3  Teilen des     ternären    Kondensationsproduktes  aus 1     Mol        Cyanurchlorid,    1     Mol        1,8-Amino-          naphthol-3,6-disulfonsäure,

      1     Mol        4-Amino-          4'-oxyazobenzol-3'-carbonsäurä    und 1     Mol          Monomethylamin    eingetragen. Nach beendeter  Kupplung wird auf 85  angewärmt und bei  dieser Temperatur durch Zufügen von Natron  lauge der     Toluolsulfonsäurerest    abgespalten.      Der Farbstoff wird mit     Natriumchlorid    aus  gefällt und getrocknet.



  Process for the production of a new dye. It has been found that a new dye is obtained if 1 mol of the diazotized coupling product is obtained from an o-ester of 1-diazo-8-oxynaphthalene-3,6-disulfonic acid with 3-amino-4-kr, esol methyl ether, 1 mole of cyanuric chloride, 1 mole of 1-amino-8-oxyrraphthaline-3,6-disulfuric acid,

          1Mo1 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mole of monomethylamine can act on one another in such a way that the diazotized coupling product in the 7-position of thel-anrino-8-oxynaphthalene-3,6-disulfonsärrre couples and a halogen of the Cyanuric chloride with the "amino group of 1-amino-8-oxynaphthalenesulfonic acid,

      a halogen of the cyanuric chloride reacts with the amino group of the 4-amirro-4'-oxyazobenzene-3'-carboxylic acid and the last halogen atom of the cyanuric chloride with the amino group of the monomethylamine and that the product thus obtained is split off the ester group is 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 1-amino-8-oxynaphthalene-4'-toluenesulfonic acid ester-3,6-disulfonic acid diazotized by coupling 1 mole of 3-amino-4 -cresol methyl ether obtained dye are diazotized and cooled into a cooled ammoniacal solution of 68.3 parts of the ternary condensation product of 1 mol of cyanuric chloride, 1 mol of 1,8-amino naphthol-3,6-disulfonic acid,

      1 mol of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mol of monomethylamine entered. When the 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 Mol des diazotierten Kupplungsproduktes aus einem o-Ester der 1-Diazo-8-oxyciaphthalin- 3,6-disulfonsäure mit 3-Amino-4-kresolmethyl- äther, 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; that 1 mol of the diazotized coupling product from an o-ester of 1-diazo-8-oxyciaphthalene-3,6-disulfonic acid with 3-amino-4-cresolmethyl ether, 1 mol of cyanuric chloride, 1 mol of 1-amino-8-oxynaphthalene -3,6-disulfonic acid, 1 Mol 4 Amino-4'-oxyazobenzol-3'-carbonsäure und 1Mol Monomethylamin derart aufeinander einwirken lässt, dass das diazotier te Kupplungsprodukt in der 7-Stellung der 1-Amino-8-oxynaphtba- lin-3,6-disulfonsäure kuppelt und ein Halogen des Cyanurchlorides mit der Aminogruppe der 1-Amino-8-oxynaphthalinsulfonsäure, 1 mol of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mol of monomethylamine can act on one another in such a way that the diazotized coupling product couples in the 7-position of the 1-amino-8-oxynaphtba- lin-3,6-disulfonic acid and a halogen of cyanuric chloride with the amino group of 1-amino-8-oxynaphthalenesulfonic acid, ein Halogen des Cyanurchlorides mit der Amino- gruppe der4-Amino-4'-oxyazobenzol-3'-carbon- säure und das letzte Halogenatom des Cyanur- chlorides mit der Aminogruppe des Mono methylamins sich umsetzt und dass man das so erhaltene Produkt zwecks Abspaltung der Estergruppe der Einwirkung eines verseifen den Mittels unterwirft. Der neue Farbstoff biidet ein dunkles Pulver, das sich in Wasser mit blaugrüner Farbe löst. a halogen of the cyanuric chloride with the amino group of the 4-amino-4'-oxyazobenzene-3'-carboxylic acid and the last halogen atom of the cyanuric chloride reacts with the amino group of the monomethylamine and that the product obtained in this way is reacted for the purpose of splitting off 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. 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.
CH161485D 1931-12-17 1931-12-17 Process for the production of a new dye. CH161485A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH161488T 1931-12-17
CH161485T 1931-12-17
CH159668T 1931-12-17

Publications (1)

Publication Number Publication Date
CH161485A true CH161485A (en) 1933-04-30

Family

ID=27177412

Family Applications (1)

Application Number Title Priority Date Filing Date
CH161485D CH161485A (en) 1931-12-17 1931-12-17 Process for the production of a new dye.

Country Status (1)

Country Link
CH (1) CH161485A (en)

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