CH308455A - Process for the preparation of a metallizable disazo dye. - Google Patents

Process for the preparation of a metallizable disazo dye.

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Publication number
CH308455A
CH308455A CH308455DA CH308455A CH 308455 A CH308455 A CH 308455A CH 308455D A CH308455D A CH 308455DA CH 308455 A CH308455 A CH 308455A
Authority
CH
Switzerland
Prior art keywords
acid
disazo dye
dependent
orange
metallizable
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 CH308455A publication Critical patent/CH308455A/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 be  steht,

   dass man 2     Mol    der durch Kuppeln von       diazoticrter        2-Amino-5-nitrobenzol-l-carbon-          säure    mit     1-Phenyl-3-methyl-5-pyrazolon-4'-          sulfonsäure    und nachfolgendes Reduzieren  der     Nitrogruppe    zur     Aminogruppe    erhält  liehen     Aminomonoazoverbindung    mit 1     Mol     eines     Fumarsäuredihalogenides    umsetzt.  



  Im nachfolgenden Beispiel bedeuten die  Teile Gewichtsteile, und die Prozente sind in  Gewichtsprozenten angegeben.  



  <I>Beispiel:</I>  44,7 Teile der durch Kuppeln von     diazo-          tierter        2-Amino-5-nitrobenzol-l-carbonsäure     mit     1-Phenyl-3-methyl5-pyrazolon-4'-sulfon-          säure    und nachfolgendes Reduzieren der       Nitrogrüppe    zur     Aminogruppe    erhältlichen       Aminomonoazoverbindung    werden     als        Dina-          triumsalz    in 1500 Teilen Wasser gelöst.

   Die       Lösung    wird mit 5 Teilen     Lithiumcarbonat     und dann bei 5 bis 8  unter gutem Rühren  innerhalb von 2 ?/. bis 3 Stunden gleichmässig  mit so viel einer 10     1/nigen    Lösung von     Fumar-          säuredichlorid        in    Chlorbenzol versetzt, bis     in.     der Kondensationslösung keine freie     Amino-          gruppe    mehr     nachweisbar    ist. Der so gewon  nene     Disazofarbstoff    wird nach bekannten  Methoden     isoliert.     



  Der neue,     metallisierbare        Disazofarbstoff     ist ein orangegelbes Pulver, das sich in kon  zentrierter Schwefelsäure und in Wasser mit    gelber Farbe löst. Seine     gekupferten    Färbun  gen auf     Celiulosefasern    sind     gelbstichig     orange. Die in Substanz     hergestellte    Kupfer  komplexverbindung des     Disazofarbstoffes     färbt     Zellulosefasern    ebenfalls in     gelbstichig     orangen Tönen von     ausgezeichneten        Licht-          und        Nassechtheitseigenschaften.  



  <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 production of a metallizable disazo dye, which is

   that 2 moles of the aminomonoazo compound borrowed by coupling diazotic 2-amino-5-nitrobenzene-1-carboxylic acid with 1-phenyl-3-methyl-5-pyrazolone-4'-sulfonic acid and then reducing the nitro group to the amino group are obtained 1 mol of a fumaric acid dihalide.



  In the example below, parts are parts by weight and percentages are percentages by weight.



  <I> Example: </I> 44.7 parts of the acid obtained by coupling diazotized 2-amino-5-nitrobenzene-1-carboxylic acid with 1-phenyl-3-methyl5-pyrazolone-4'-sulfonic acid and the following Reduction of the nitro group to the amino group available amino monoazo compounds are dissolved as dinatrium salt in 1500 parts of water.

   The solution is mixed with 5 parts of lithium carbonate and then at 5 to 8 with good stirring within 2? /. For up to 3 hours, enough of a 10 liter solution of fumaric acid dichloride in chlorobenzene was added uniformly until no free amino group can be detected in the condensation solution. The disazo dye thus won is isolated by known methods.



  The new, metallizable disazo dye is an orange-yellow powder that dissolves in concentrated sulfuric acid and in water with a yellow color. Its coppered colorations on cellulose fibers are yellowish orange. The copper complex compound of the disazo dye, produced in bulk, also dyes cellulose fibers in yellowish orange tones with excellent light and wet fastness properties.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines metalli- sierbaren Disazofarbstoffes, dadurch gekenn zeichnet, dass man 2 Mol der durch Kuppeln von diazotierter 2-Amino-5-nitrobenzol-l-car- bonsäure mit 1-Phenyl-3-methyl-5-pyrazolon- 4'-sulfonsäure und nachfolgendes Reduzieren der Nitrogruppe zur Aminogruppe erhältli chen Aminomonoazoverbindung mit 1 Mol eines <RTI PATENT CLAIM: Process for the preparation of a metallizable disazo dye, characterized in that 2 mol of the 2-amino-5-nitrobenzene-1-carboxylic acid obtained by coupling with 1-phenyl-3-methyl-5-pyrazolone 4'-sulfonic acid and subsequent reduction of the nitro group to the amino group available aminomonoazo compound with 1 mol of <RTI ID="0001.0069"> Fumarsäuredihalogenides umsetzt. Der neue, metallisierbare Disazofarbstoff ist ein, orangegelbes Pulver, das sich in kon zentrierter Schwefelsäure und in Wasser mit gelber Farbe löst. Seine gekupferten Färbungen auf Cellulosefasern sind gelb stichig orange. ID = "0001.0069"> converts fumaric acid dihalides. The new, metallizable disazo dye is an orange-yellow powder that dissolves in concentrated sulfuric acid and in water with a yellow color. His coppery colorations on cellulose fibers are yellow, pungent orange. Die in Substanz hergestellte Kupferkomplexverbindung des Disazofarb- stoffes färbt Zellulosefasern ebenfalls in gelbstichig orangen Tönen. von ausgezeich neten Licht- und Nasseehtheitseigenschaften. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man :die Umsetzung in wässrigem Medium vornimmt. 2. The copper complex compound of the disazo dye, which is produced in bulk, also dyes cellulose fibers in yellowish orange tones. excellent light and wetness properties. 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. 4. 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. Process according to patent claim and dependent claims 1 and 2, characterized in that fumaric acid dihalide is chosen as the fumaric acid dihalide. 4th Verfahren nach Patentanspruch und Unteransprüchen 1 bis 3, dadurch gekenn zeichnet, dass man als säurebindendes Mittel Lithiumcarbonat wählt. Method according to claim and dependent claims 1 to 3, characterized in that lithium carbonate is selected as the acid-binding agent.
CH308455D 1952-04-30 1952-04-30 Process for the preparation of a metallizable disazo dye. CH308455A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH308455T 1952-04-30
CH304388T 1956-05-03

Publications (1)

Publication Number Publication Date
CH308455A true CH308455A (en) 1955-07-15

Family

ID=25734806

Family Applications (1)

Application Number Title Priority Date Filing Date
CH308455D CH308455A (en) 1952-04-30 1952-04-30 Process for the preparation of a metallizable disazo dye.

Country Status (1)

Country Link
CH (1) CH308455A (en)

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