CH308469A - Process for the preparation of a metallizable disazo dye. - Google Patents

Process for the preparation of a metallizable disazo dye.

Info

Publication number
CH308469A
CH308469A CH308469DA CH308469A CH 308469 A CH308469 A CH 308469A CH 308469D A CH308469D A CH 308469DA CH 308469 A CH308469 A CH 308469A
Authority
CH
Switzerland
Prior art keywords
acid
amino
dependent
ethoxy
fumaric acid
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Sandoz
Original Assignee
Ag Sandoz
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 Ag Sandoz filed Critical Ag Sandoz
Publication of CH308469A publication Critical patent/CH308469A/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
    • C09B43/145—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with polycarboxylic acids
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds
    • C09B45/28—Disazo or polyazo compounds containing copper

Landscapes

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

Description

  

  <B>Zusatzpatent</B>     zum    Hauptpatent Nr. 304388.    Verfahren zur Herstellung eines     metallisierbaren        Disazofarbatoffes.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines     metalli-          sierbaren        Disazofarbstoffes,    welches darin  besteht, dass man 2,     Mol    der durch     Kuppeln     von     diazotierter        2-Amino-5-nitrobenzol-l-car-          bonsäure    mit     2-Carbo-(2:

  '-äthoxy)-äthoxy-          amino-5-oxynaphthalin-7-sulfonsäure    und       nachfolgende    Reduktion der Nitrogruppe zur       Aminogruppe    erhältlichen     Aminomonoazover-          bindung    mit 1     Mol    eines     Fumarsäuredihalo-          genides    umsetzt.  



  Im nachfolgenden Beispiel bedeuten die  Teile Gewichtsteile.  



  <I>Beispiel:</I>  51,8 Teile der durch Kuppeln von     diazo-          tierter        2-Amino-5-nitrobenzol-1-carbonsäure     mit     2-Ca.rbo-(2'-äthoxy)-äthoxyamino-5,-oxy-          iiaphthalin-7-sulfonsäure    und anschliessende  Überführung der Nitrogruppe in die     Amino-          gruppe    erhältlichen     Aminomonoazoverbindung     werden in Form des     Dilithiumsalzes    in 4000  Teilen Wasser gelöst.

   Die Lösung versetzt man  gleichmässig innerhalb von etwa 7 Stunden  mit einer Lösung von 9,2 Teilen     Fumarsäure-          dichlorid    in 40 Teilen Chlorbenzol. Durch  gelegentlichen Zusatz von wenig     Lithium-          earbonat    wird der     pH-Wert    der Kondensations  lösung stets zwischen 5,5 und 7 gehalten. Nach       erfolgter    Kondensation erwärmt man die  Masse auf 90 -     9,5 ,    salzt     daraus    den gebilde  ten     Disazofarbstoff    aus, filtriert ihn ab und  trocknet ihn.

      Der neue,     metallisierbare        Disazofarbstoff     löst sich in Wasser und in konzentrierter  Schwefelsäure mit roter Farbe und färbt  Baumwolle und Fasern aus regenerierter       Cellu    lose in roten Tönen, welche, mit einem  kupferabgebenden Mittel behandelt, ausge  zeichnet licht-, wasch- und schweissecht sind.



  <B> Additional patent </B> to the main patent No. 304388. Process for the production of a metallizable disazo carbate. The subject of the present patent is a process for the preparation of a metallizable disazo dye, which consists in that 2, mol of the coupling of diazotized 2-amino-5-nitrobenzene-1-carboxylic acid with 2-carbo- (2:

  '-ethoxy) -ethoxy-amino-5-oxynaphthalene-7-sulfonic acid and subsequent reduction of the nitro group to the amino group, the aminomonoazo compound obtainable is reacted with 1 mol of a fumaric acid dihalogenide.



  In the following example, the parts are parts by weight.



  <I> Example: </I> 51.8 parts of the compound obtained by coupling diazotized 2-amino-5-nitrobenzene-1-carboxylic acid with 2-Ca.rbo- (2'-ethoxy) -ethoxyamino-5, - Oxy-iiaphthalene-7-sulfonic acid and subsequent conversion of the nitro group into the amino group, the aminomonoazo compound obtainable is dissolved in 4000 parts of water in the form of the dilithium salt.

   A solution of 9.2 parts of fumaric acid dichloride in 40 parts of chlorobenzene is added evenly to the solution over a period of about 7 hours. The pH of the condensation solution is always kept between 5.5 and 7 by occasionally adding a little lithium carbonate. After the condensation has taken place, the mass is heated to 90-9.5, the disazo dye formed is salted out, filtered off and dried.

      The new, metallizable disazo dye dissolves in water and in concentrated sulfuric acid with a red color and dyes cotton and fibers made from regenerated cellulose in red shades, which, when treated with a copper-releasing agent, are excellent lightfast, washfast and perspiration-resistant.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines metalli- sierbaren Disazofarbatoffes, dadurch gekenn zeichnet, dass man 2 Mol der durch Kuppeln von diazotierter 2-Amino-5-nitrobenzol-l-car- bonsäure mit 2 - Carbo - (2'- äthoxy) PATENT CLAIM: Process for the production of a metallizable disazo carbate, characterized in that 2 moles of the 2-amino-5-nitrobenzene-1-carboxylic acid obtained by coupling with 2-carbo- (2'-ethoxy) - äthoxy- amino-5-oxynaphthalin-7-sulfonsäure und nachfolgende Reduktion der Nitrogruppe zur Aminogruppe erhältlichen Aminomonoazover- bindung mit 1 Mol eines Fumarsäuredihalo- genides umsetzt. - Ethoxy-amino-5-oxynaphthalene-7-sulfonic acid and subsequent reduction of the nitro group to the amino group available aminomonoazo compound with 1 mol of a fumaric acid dihalogen. Der neue, metallisierbare Disazofarbstoff löst sich in Wasser und in konzentrierter Schwefelsäure mit roter Farbe und färbt Baumwolle und Fasern aus regenerierter Cellulose in roten Tönen, welche, mit einem kupferabgebenden Mittel behandelt, ausge zeichnet licht-, wasch- und schweissecht sind. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da- dureh gekennzeichnet, dass man die Umsetzung in wässrigem Medium vornimmt. 2. The new, metallizable disazo dye dissolves in water and in concentrated sulfuric acid with a red color and dyes cotton and fibers made of regenerated cellulose in red tones, which, when treated with a copper-releasing agent, are extremely light, wash and perspiration resistant. SUBClaims: 1. Method according to claim, characterized in that the reaction is carried out in an aqueous medium. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Umsetzung in Gegenwart eines säurebindenden Mittels vornimmt. 3. Verfahren nach Patentanspruch und Unteransprüchen 1 und 2, dadurch gekenn zeichnet, dass man als Fumarsäuredihalogenid Fumarsäurediehlorid wählt. Verfahren nach Patentanspruch und Unteransprüchen 1- 3, dadurch gekennzeich net, dass man als säurebindendes Mittel Lithiumcarbonat wählt. Process according to patent claim and dependent claim 1, characterized in that the reaction is carried out in the presence of an acid-binding agent. 3. The method according to claim and dependent claims 1 and 2, characterized in that fumaric acid dihalide is selected as the fumaric acid dihalide. Process according to patent claim and dependent claims 1 to 3, characterized in that lithium carbonate is selected as the acid-binding agent.
CH308469D 1952-04-30 1952-04-30 Process for the preparation of a metallizable disazo dye. CH308469A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH308469T 1952-04-30
CH304388T 1956-05-03

Publications (1)

Publication Number Publication Date
CH308469A true CH308469A (en) 1955-07-15

Family

ID=25734820

Family Applications (1)

Application Number Title Priority Date Filing Date
CH308469D CH308469A (en) 1952-04-30 1952-04-30 Process for the preparation of a metallizable disazo dye.

Country Status (1)

Country Link
CH (1) CH308469A (en)

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