CH275072A - Process for the preparation of an azo dye derivative. - Google Patents

Process for the preparation of an azo dye derivative.

Info

Publication number
CH275072A
CH275072A CH275072DA CH275072A CH 275072 A CH275072 A CH 275072A CH 275072D A CH275072D A CH 275072DA CH 275072 A CH275072 A CH 275072A
Authority
CH
Switzerland
Prior art keywords
acid
azo dye
brown
dye derivative
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH275072A publication Critical patent/CH275072A/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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • 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
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
    • C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffderivates.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoffderivat    gelangt, wenn    man auf ein     Mol    des     Azofarbstoffes    der  Formel  
EMI0001.0005     
    mindestens zwei     Mol    eines     Halogenides    der       Chloressigsäure-sulfonsäure    einwirken lässt.  



  Das neue Farbstoff     derivat    stellt ein braun  oranges Pulver dar, das sich in Wasser mit       braunoranger    Farbe leicht und klar auflöst  und nach Zugabe von verdünnten Alkalien  sofort den unlöslichen     tschwarzbraunen        Aüs-          gangsazofarbstoff    wieder abspaltet. Es eignet  sich zur Herstellung von Textilfärbungen und       zur    Verwendung im Zeugdruck.  



  Der Ausgangsfarbstoff der angegebenen  Formel lässt sich in einfacher Weise herstel  len durch Vereinigen von     diazotiertem        4-Chlor-          2-methyl-l-aminobenzol    mit     2-Oxydiphenylen-          oxyd-3-carbonsäure-2',5'-dimethoxyanilid.     



  Über die beim vorliegenden. Verfahren als  Ausgangsstoffe dienenden     Halogenide    der       Chloressigsäure-sulfonsäure,    über die Durch  führung der Reaktion und über deren     Mecha:            nismus    sind nähere Angaben, welche auch für  das vorliegende Patent gelten, im Haupt  patent zu finden.  



  <I>Beispiel:</I>  15 Teile     Chloressigsäure-sulfonsäur-e-    wer  den mit 100     Volumteilen    trockenem     Pyridin     vermischt, 7,6 Teile des     Azofarbstoffes    aus       diazotiertem        4-Chlor-2-methyl-l-aminobenzol.     und     2-Oxydiphenylenoxyd-3-carbons4,ure-2',5'-          dimethoxyanilid    zugefügt und dann bei 30 bis  40  9 Teile     Phosgen    eingeleitet.

   Nach erfolg  ter Aufnahme des     Phosgens    wird das Reak  tionsgemisch auf 75 bis 80  erwärmt, wobei  nach etwa 10 bis 20 Minuten Reaktionsdauer  das Pigment in Lösung gegangen und die       Acylierung    beendet ist. Eine Probe des Reak  tionsgemisches ist im Wasser klar löslich ge  worden. Das auf Raumtemperatur abgekühlte  Reaktionsgemisch wird nun unter Rühren in  eine Mischung aus 375 Teilen Wasser und      52,5     Teilen        konz.    Schwefelsäure eingegossen,  25 Teile     Natriumchlorid    zugesetzt und das  Ganze auf 40 bis     50     erwärmt, wobei das  harzig ausgeschiedene Reaktionsprodukt sich  gut absetzt.

   Nach dem Abgiessen des sauren       Pyridinwassers    wird der Rückstand in 300  Teilen Wasser gelöst und mit 30 Teilen Na  triumchlorid wieder     ausgesalzen.    Das in fester    Form ausgeschiedene     Reaktionsprodukt    wird  abgesaugt und im     Vakuum    bei 40 bis 50  ge  trocknet.



  Process for the preparation of an azo dye derivative. It has been found that a valuable azo dye derivative is obtained if one mole of the azo dye of the formula
EMI0001.0005
    at least two moles of a halide of chloroacetic acid sulfonic acid can act.



  The new dye derivative is a brown-orange powder that dissolves easily and clearly in water with a brown-orange color and immediately splits off the insoluble, black-brown starting azo dye after adding dilute alkalis. It is suitable for the production of textile dyeings and for use in fabric printing.



  The starting dye of the formula given can be produced in a simple manner by combining diazotized 4-chloro-2-methyl-1-aminobenzene with 2-oxydiphenylene oxide-3-carboxylic acid-2 ', 5'-dimethoxyanilide.



  About the present. Processes used as starting materials halides of chloroacetic acid-sulfonic acid, about the implementation of the reaction and its mechanism, more information, which also apply to the present patent, can be found in the main patent.



  <I> Example: </I> 15 parts of chloroacetic acid-sulfonic acid-e- are mixed with 100 parts by volume of dry pyridine, 7.6 parts of the azo dye from diazotized 4-chloro-2-methyl-1-aminobenzene. and 2-Oxydiphenylenoxyd-3-carbons4, ure-2 ', 5'-dimethoxyanilid added and then introduced at 30 to 40 9 parts of phosgene.

   After the phosgene has been taken up, the reaction mixture is heated to 75 to 80, the pigment going into solution and the acylation being complete after a reaction time of about 10 to 20 minutes. A sample of the reaction mixture has become clearly soluble in water. The reaction mixture, cooled to room temperature, is then poured into a mixture of 375 parts of water and 52.5 parts of conc. Poured in sulfuric acid, added 25 parts of sodium chloride and heated the whole thing to 40 to 50, the resinous reaction product precipitating out well.

   After the acidic pyridine water has been poured off, the residue is dissolved in 300 parts of water and salted out again with 30 parts of sodium chloride. The reaction product precipitated in solid form is filtered off with suction and dried at 40 to 50 in vacuo.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffderivates, dadurch gekennzeichnet, dass man auf ein Mol des Azofarbstoffes der For mel EMI0002.0013 mindestens zwei Mol eines Halogenides der Chloressigsäure-sülfonsäure einwirken lässt. PATENT CLAIM: Process for the preparation of an azo dye derivative, characterized in that one mole of the azo dye of the formula EMI0002.0013 at least two moles of a halide of chloroacetic acid sulphonic acid can act. Das neue Farbstoffderivat stellt ein braun oranges Pulver dar, das sich in Wasser mit braimoranger Farbe leicht und klar auflöst und nach Zugabe von verdünnten Alkalien sofort den unlöslichen schwarzbraunen Aus- gangsazofarbstoff wieder abspaltet. UNTERANSPRÜCHE: 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man in Gegenwart einer tertiären Base arbeitet. 2. Verfahren gemäss Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man in Gegenwart von Pyridin arbeitet. 3. The new dye derivative is a brown-orange powder, which dissolves easily and clearly in water with a brown-orange color and immediately splits off the insoluble black-brown starting azo dye after adding dilute alkalis. SUBClaims: 1. Process according to claim, characterized in that one works in the presence of a tertiary base. 2. The method according to claim and dependent claim 1, characterized in that one works in the presence of pyridine. 3. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man ein Säure halogenid verwendet, das man erhält, wenn man Chloressigsäure-sulfonsäure in Gegenwart einer tertiären Base mit einem aromatischen Sulfonsäurechlorid behandelt. 4. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man ein Säure halogenid verwendet, das man erhält, wenn man Chloressigsäure-sulfonsäure in Gegen wart einer tertiären Base mit Phosgen be handelt. Process according to patent claim, characterized in that an acid halide is used which is obtained when chloroacetic acid-sulfonic acid is treated with an aromatic sulfonic acid chloride in the presence of a tertiary base. 4. The method according to claim, characterized in that an acid halide is used, which is obtained when chloroacetic acid-sulfonic acid is treated with phosgene in the presence of a tertiary base.
CH275072D 1948-06-02 1949-04-05 Process for the preparation of an azo dye derivative. CH275072A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH270831T 1948-06-02

Publications (1)

Publication Number Publication Date
CH275072A true CH275072A (en) 1951-04-30

Family

ID=4477931

Family Applications (4)

Application Number Title Priority Date Filing Date
CH275073D CH275073A (en) 1948-06-02 1948-06-02 Process for the preparation of an azo dye derivative.
CH270831D CH270831A (en) 1948-06-02 1948-06-02 Process for the preparation of an azo dye derivative.
CH275071D CH275071A (en) 1948-06-02 1948-11-12 Process for the preparation of an azo dye derivative.
CH275072D CH275072A (en) 1948-06-02 1949-04-05 Process for the preparation of an azo dye derivative.

Family Applications Before (3)

Application Number Title Priority Date Filing Date
CH275073D CH275073A (en) 1948-06-02 1948-06-02 Process for the preparation of an azo dye derivative.
CH270831D CH270831A (en) 1948-06-02 1948-06-02 Process for the preparation of an azo dye derivative.
CH275071D CH275071A (en) 1948-06-02 1948-11-12 Process for the preparation of an azo dye derivative.

Country Status (4)

Country Link
CH (4) CH275073A (en)
DE (2) DE823737C (en)
FR (2) FR987373A (en)
GB (2) GB662572A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE976515C (en) * 1952-05-01 1963-10-31 Hoechst Ag Process for the preparation of water-soluble sulfochloroacetic ester salts of leukokuepen dyes
US2852554A (en) * 1956-07-12 1958-09-16 Du Pont Alpha-sulfopolyfluoromonocarboxylic acids and derivatives hydrolyzable thereto

Also Published As

Publication number Publication date
GB662573A (en) 1951-12-05
DE831718C (en) 1952-02-18
CH275073A (en) 1951-04-30
CH275071A (en) 1951-04-30
DE823737C (en) 1951-12-06
CH270831A (en) 1950-09-30
GB662572A (en) 1951-12-05
FR987725A (en) 1951-08-17
FR987373A (en) 1951-08-13

Similar Documents

Publication Publication Date Title
CH275072A (en) Process for the preparation of an azo dye derivative.
CH280726A (en) Process for the preparation of an azo dye derivative.
CH280727A (en) Process for the preparation of an azo dye derivative.
CH232280A (en) Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
DE744219C (en) Process for the production of acidic dyes of the anthraquinone series
DE909455C (en) Process for the preparation of dicarboxylic acid dihalamides
DE589566C (en) Process for the preparation of yellow stain dyes
DE541629C (en) Process for the preparation of sulfonated oxydi- or triarylmethane compounds
DE907177C (en) Process for the preparation of 1-arylamino-5-oxynaphthalene-7-sulfonic acids
DE877764C (en) Process for the production of triphenylmethane off-cuts containing sulfone groups
DE530826C (en) Process for the preparation of oxysulfamic acids
CH276418A (en) Process for the preparation of an azo dye derivative.
CH285370A (en) Process for the preparation of an azo dye derivative.
CH280729A (en) Process for the preparation of an azo dye derivative.
CH282626A (en) Process for the preparation of an azo dye derivative.
CH280728A (en) Process for the preparation of an azo dye derivative.
CH308489A (en) Process for the preparation of a dye of the dioxazine series.
CH285372A (en) Process for the preparation of an azo dye derivative.
CH264495A (en) Process for the production of a vat dye.
CH307169A (en) Process for the production of a copper-containing azo dye.
CH285369A (en) Process for the preparation of an azo dye derivative.
CH261865A (en) Process for the production of a vat dye.
CH261868A (en) Process for the production of a vat dye.
CH249013A (en) Process for the preparation of an ester type azo dye derivative.
CH285371A (en) Process for the preparation of an azo dye derivative.