CH234517A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH234517A
CH234517A CH234517DA CH234517A CH 234517 A CH234517 A CH 234517A CH 234517D A CH234517D A CH 234517DA CH 234517 A CH234517 A CH 234517A
Authority
CH
Switzerland
Prior art keywords
amino
methyl
acid
urea derivative
weight
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 CH234517A publication Critical patent/CH234517A/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
    • C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene

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

Description

  

      Terfahr    en zur Herstellung eines     Harnstoffderivates.       Es wurde .gefunden,     d:ass:        main    zu einem  neuen     Harustoffderivat    gelaugt, das gleich  zeitig einen     wertvollen        Azofarbstoff        darstellt.     wenn man auf 1     Mol    :der     2.Methyl-4-(4"-          amino)        -benzoylamnno-    2''     -ogy-1,1'-a::zobenzol-          3'-oarbonsäuTe-5'-sulfo:

  nsäure    und 1     Mol        4-          Amino-3-methyl-4',ogy-1,1'        az-obienzol-.3'-car-          bonsäure    1     Mo:l        Phosgen        einwirken    lässt.  



  Der neue Farbstoff stellt     enn    braunes  Pulver dar,     :das        Baumwolle    in schwach     aJka-          lisahem    Bade,     @d;as    mit     einer    Kupfersalzlösung  aus Kupfersulfat und weinsaurem Natrium       versetzt    wurde, in     waschechtem        rotistichig     gelbem     Tone    anfärbt.

           Beispiel:     35,1     Gewichtsteile        des.        MonoazoTarbstoffes     aus     diazotierter        1-Amino-2-o:gyb:enz:ol-3-carb-          ogy-5-,sulfo#nsäure    und     1-Methyl-3-,amin:oben-          zo    1 werden als     Na-Salz    unter Zusatz von 13,5       Gewichtsteilen:

          Natriumacetat    in 250     Ge-          wichteteilen    Wasser gelöst.     Diese    Lösung  wird bei     etwa    60      mit    18,5     Gewichtsteilen        4-          Nitrob:enzo@ylchlo@rid,    die mit 5 Gewichtstei-         len    Aceton versetzt wurden, behandelt.

   Man       reduziert    das     .gebildete        Nitrob@enzoylprodukt     mit 42     Gewichtsteilen        kristallisiertem        Na-          triumsulfi:

  d,    die in 75 Gewichtsteilen Wasser       gelöA    wurden,     bei    65-7.0  zum     Aminoben-          zoylpro,dukt.        Das          Reduktions-          proldukt    wird mit 27,1     Gewichtsteilen    4  Amino-     3-miethyl-4'-oxy-1,L'-,azebenzol-3'-oar-          bonsäure    unter Zusatz von     Natriumearbonat     bis zur     @cleutläclhenalkalischen        Reaktion    in  4000     Gewichtsteilen        Wasser    :

  gelöst     und    wäh  rend 24     :Stunden        unter        Ritihren        bei        30-40      mit     Phosgen    behandelt,     bis    sich keine freie       NHZ-Grupp@e    mehr     nachweisen        lässt.    Das     aus-          ,geschiedene        unsymmetrische        Harnstoffdenivat     wird als     Natriumsalz    gefällt,     filtriert    und ge  trocknet.



      Terfahr en for the production of a urea derivative. It was found that leached to a new uranium derivative, which at the same time represents a valuable azo dye. if one mole: the 2nd methyl-4- (4 "- amino) -benzoylamnno- 2" -ogy-1,1'-a :: zobenzene- 3'-oarboxylic acid-5'-sulfo:

  Acid and 1 mol of 4-amino-3-methyl-4 ', ogy-1,1' az-obienzol-.3'-carboxylic acid 1 mol: l phosgene to act.



  The new dye is a brown powder: the cotton in a weakly alkaline bath, which has been mixed with a copper salt solution of copper sulfate and tartrate of sodium, is dyed in a washable, reddish-yellow shade.

           Example: 35.1 parts by weight of the. Monoazo dye from diazotized 1-amino-2-o: gyb: enz: ol-3-carbogy-5-, sulfonic acid and 1-methyl-3-, amine: above-zo 1 as Na salt with the addition of 13.5 parts by weight:

          Sodium acetate dissolved in 250 parts by weight of water. This solution is treated at about 60 with 18.5 parts by weight of 4-nitrob: enzo @ ylchloride to which 5 parts by weight of acetone have been added.

   The nitrobenzoyl product formed is reduced with 42 parts by weight of crystallized sodium sulfi:

  d, which were dissolved in 75 parts by weight of water, at 65-7.0 to the aminoben- zoylpro, product. The reduction prolduct is mixed with 27.1 parts by weight of 4 amino-3-methyl-4'-oxy-1, L '-, azebenzene-3'-oarboxylic acid with the addition of sodium carbonate up to the @ cleutlhen-alkaline reaction in 4000 parts by weight of water:

  dissolved and treated with phosgene for 24: hours while stirring at 30-40, until no free NHZ groups can be detected any more. The precipitated, unsymmetrical urea derivative is precipitated as the sodium salt, filtered and dried.

Claims (1)

PATENTANSPRUCH: VerfähTen zur Herstellung einfies Harn- stoffderivates, dadurch gekennzeichnet, ,dass man, auf 1 Mal der 2.Methyl-4-(4"-amino) benzoylamino,-2'-ogy-1,1'-azobeanzo#l-3'-oarbon- s äure-5'-sudfonsäure und 1 Mol 4-Amino-3- rnethyl - 4' -,ogy -1, PATENT CLAIM: Capable of producing a urea derivative, characterized in that the 2nd methyl-4- (4 "-amino) benzoylamino, -2'-ogy-1,1'-azobeanzo # l- 3'-carbonic acid-5'-sudfonic acid and 1 mol of 4-amino-3-methyl - 4 '-, ogy -1, 1'-!azobenzo#l-3'-carbons äur e 1 Mol Phosgen .einwirken lässt. Der neue Farbstoff stellt ein, braunes Pulver dar, das Baumwod.le in schwach alka- lischem Bade, das mit einer Kupfersalzlösung aus Kupfersulfat und weinsaurem Natrium versetzt wurde, in waschechtem rotstiehig gelbem Tone anfärbt.. 1 '-! Azobenzo # l-3'-carboxylic acid e 1 mole of phosgene. The new dye is a brown powder that stains cotton in a weakly alkaline bath to which a copper salt solution of copper sulfate and tartaric acid sodium has been added, turning it into a washable, reddish-yellow shade.
CH234517D 1940-11-22 1940-11-22 Process for the production of a urea derivative. CH234517A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH232121T 1940-11-22
CH234517T 1940-11-22

Publications (1)

Publication Number Publication Date
CH234517A true CH234517A (en) 1944-09-30

Family

ID=25727675

Family Applications (1)

Application Number Title Priority Date Filing Date
CH234517D CH234517A (en) 1940-11-22 1940-11-22 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH234517A (en)

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