CH159668A - Process for the production of a new dye. - Google Patents

Process for the production of a new dye.

Info

Publication number
CH159668A
CH159668A CH159668DA CH159668A CH 159668 A CH159668 A CH 159668A CH 159668D A CH159668D A CH 159668DA CH 159668 A CH159668 A CH 159668A
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 CH159668A publication Critical patent/CH159668A/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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/18—Trisazo or higher polyazo dyes
    • C09B33/22—Trisazo dyes of the type A->B->K<-C

Landscapes

  • 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 diano  tierten Kupplungsproduktes aus     ei_nen@.@-Est@r.     der     1-Diazo-8-oxynaphthalin-4,6-disulfosäure     mit 3 -     Amino    - 4-     kresolmethyläther,    1     Mol          Cyanureblorid,    1     Mol        1-Amino-8-oxynaphtha-          lin-3,6-disulfosäure,

      1     Mol        4-Amino-4'-oxy-          azobenzol-3'-carbonsäure    und 1     1M1    Anilin  derart aufeinander einwirken lässt, dass das  dianotierte Kupplungsprodukt in der     7-Stel-          lung    der     1-Amino-8-oxynaphthalin-3,6-disuIfo-          säure    kuppelt und ein Halogen des     Cyanur-          chlorides    mit der     Aminogruppe    der     1-Amino-          8-oxynaphthalinsulfosäure,

      ein Halogen des       Cyanurchlorides    mit der     Aminogruppe    der       4-Amino-4'-oxyazobenzol-3'-carbonsäure    und  das letzte Halogenatom des     Cyanurchlorides     mit der     Aminogruppe    des Anilins 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. 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'       toluolsulfonsäureester-4,6-disulfösäure    und  1     Mol        3-Amino-4-kresolmethyläther    erhalte  nen Farbstoffes werden dianotiert und in eine  abgekühlte     ammoniakalische    Lösung von 74,5  Teilen des     ternären    Kondensationsproduktes  aus 1     Mol        Cyanurchlorid,    1     Mol        1,8-Amino-          riaphthol-3,6-disulfosäure,

      1     Mol        4-Amino-4'-          oxyazobenzol-3'-carbonsäure    und     1Mol    Anilin  eingetragen. Nach beendeter Kupplung wird  auf 85   angewärmt und bei dieser Tempe  ratur durch Zufügen von Natronlauge der       Toluolsulfosäurerest    abgespalten. Der Farb  stoff 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 diano-oriented coupling product from ei_nen @. @ - Est @ r. of 1-diazo-8-oxynaphthalene-4,6-disulfonic acid with 3-amino-4-cresol methyl ether, 1 mol of cyanuric chloride, 1 mol of 1-amino-8-oxynaphthalene-3,6-disulfonic acid,

      1 mol of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 1M1 of aniline can act on one another in such a way that the dianotated coupling product in the 7-position of the 1-amino-8-oxynaphthalene-3,6- disulfonic acid and a halogen of cyanuric chloride with the amino group of 1-amino-8-oxynaphthalene sulfonic acid,

      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 with the amino group of the aniline and that the product thus obtained for the purpose of cleavage of the ester group 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 dye obtained by coupling 1 mole of dianotated 1-amino-8-oxynaphthalene-4'-toluenesulfonic acid ester-4,6-disulfoic acid and 1 mol of 3-amino-4-cresol methyl ether are dianotized and poured into a cooled ammoniacal solution of 74.5 parts of the ternary condensation product of 1 mol of cyanuric chloride, 1 mol of 1,8-amino riaphthol-3,6-disulfonic acid,

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

Claims (1)

PATENTANSPP,ÜCH,: Verfahren zur Herstellung eines neuen Farbstoffes, dadurch gekennzeichnet, dass man 1 1Mol des diazotierten Kupplungsproduktes aus einem o-Ester der 1-Diazo-8-oxynaphtha- lin-4.6-disulfosäure mit 3-Amino-4-kresol- methyläther, 1 Mol Cyanurchlorid, 1 Mol 1 -Amino-8-oxynaphthalin-3,6-disulfosäure, PATENTANSPP, ÜCH ,: Process for the preparation of a new dye, characterized in that 1 1Mol of the diazotized coupling product from an o-ester of 1-diazo-8-oxynaphthalin-4,6-disulfonic acid with 3-amino-4-cresol methyl 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 1 lNTol Anilin derart. aufeinander einwir ken lässt, dass das diazotierte Kupplungspro dukt in der 7-Stellung der 1-Amino-8-oxy- naphthalin-3,6-disulfosäure kuppelt und ein Ha logen des Cyan urchlorides mit der Aminogruppe der 1-Amino-8-oxynaphthalinsulfosäure, 1 mole of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 liter of aniline like this. The fact that the diazotized coupling product couples in the 7-position of the 1-amino-8-oxynaphthalene-3,6-disulfonic acid and a halogen of the cyano chloride with the amino group of the 1-amino-8-oxynaphthalenesulfonic acid interacts with one another , ein Halogen des Cyanurchlorides mit der Amino- Kruppe der 4-Amino-4'-oxyazobenzol-3'-car- bonsäüre und das letzte Halogenatom des Cyanurchlorides mit der Aminogruppe des Anilins 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. 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 aniline and that the product obtained in this way is reacted for the purpose of cleavage of the ester group 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.<B>,</B> He produces green tones on cotton from dye baths made with soft or hard water; which are characterized by their excellent lightfastness. <B>, </B>
CH159668D 1931-12-17 1931-12-17 Process for the production of a new dye. CH159668A (en)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number Publication Date
CH159668A true CH159668A (en) 1933-01-31

Family

ID=25717266

Family Applications (2)

Application Number Title Priority Date Filing Date
CH161488D CH161488A (en) 1931-12-17 1931-12-17 Process for the production of a new dye.
CH159668D CH159668A (en) 1931-12-17 1931-12-17 Process for the production of a new dye.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH161488D CH161488A (en) 1931-12-17 1931-12-17 Process for the production of a new dye.

Country Status (1)

Country Link
CH (2) CH161488A (en)

Also Published As

Publication number Publication date
CH161488A (en) 1933-04-30

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