CH234520A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH234520A
CH234520A CH234520DA CH234520A CH 234520 A CH234520 A CH 234520A CH 234520D A CH234520D A CH 234520DA CH 234520 A CH234520 A CH 234520A
Authority
CH
Switzerland
Prior art keywords
oxy
production
amino
urea derivative
mole
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 CH234520A publication Critical patent/CH234520A/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

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 232121.    Verfahren zur Herstellung eines     Barnstoffderivates.       Es wurde ,gefunden,     @dass,    man zu     :einem     neuen     Harnstoffderivat        gelangt,    das gleich  zeitig einen     wertvollen        Azofarb        toff    :

  darstellt,  wenn man auf 1     Mol        der        2-1Vlethyl-4-(3"-          amxno)-benzoylamino-        5-methoxy-4'-oxy-1,1'-          azobenzol    -     3'-        carbons@äure-5'-sulf        onsäure    und  1     Mol        4-Amin@o-4'-,oxy-1,1'-azob,enzol-3'-car-          bonsäure    1     Mol        Phosgen        einwirken    lässt.  



  Der neue Farbstoff     stellt.    ein     :hellbraunes     Pulver :dar,     Idas        Baumwolle    in     schwach    alka  lischem Bade,     das    mit     einer        Kup,fersalzldsung     aus Kupfersulfat und     weinsaurem        Natrium          versetzt        wurde,    in waschechtem     grünstichig     gelbem     Tone    anfärbt.  



  <I>Beispiel:</I>  38,1     Gewichtsteile    des     Monoazofarbstoffes     aus     diazotierter        1-Amino@-4-oxybenzol-3-oarb-          o.xy-5-isulfonsäure    und     1-Metbyl-3,-amino-4-          methoxybenzol    werden als     Na-Salz        unter    Zu  satz von     1,3,5        Gewichtsteilen        Natriumacetat          'an    250     Gewichtsteilen:

          Waeser        gelöst.        Diese     Lösung wird bei     :etwa.    60  mit 18,5 Gewichts-    teilen     3-Nitrobenzoylchlorid,    die     mit    5     Ge-          wichtsteilen        Aceton        versetzt        wunden,        behan-          delt.    Man     reduziert        das    ;

  gebildete     Nitro-          benzoylprodukt    mit 42 Gewichtsteilen     kri-          stallisiertem        Natriumsulfid,        @die        in    75 Ge  wichtsteilen Wasser gelöst wurden, bei 65 bis  70  zum     Aminob:enzoylpro,dukt.    Das:

       abge-          sebmedene        Reduktionsprodukt        wird    mit 25,7       (@ewichtsteälen        4-Amino-4'-oxy-1,1'-a7,oben-          zol-,

  3'-carbonsäure    unter Zusatz von     Natrium-          oarbonat        bis        zugdeutlichen        alkalischen        Reak-          tion.    in 4000     Gewichtsteilen    Wasser gelöst  und während 24     Stunden    unter     Riühzen    bei       30-40     mit     Phosgen    behandelt,

       bis    sich keine  freie     NHZ-Gruppe        mehr        nachweisen        lässt.        Dass          ausigeschiedene        Harnstoffderivat    wird als       Natriumsalz        gefällt,        filtriert    und     :getrocknet.  



  <B> Additional patent </B> to main patent no. 232121. Process for the production of a barn material derivative. It was found @that, one arrives at: a new urea derivative, which at the same time is a valuable azo dye:

  represents if one mole of 2-1Vlethyl-4- (3 "- amxno) -benzoylamino-5-methoxy-4'-oxy-1,1'-azobenzene-3'-carboxylic acid-5'-sulf onic acid and 1 mol of 4-amin @ o-4 '-, oxy-1,1'-azob, enzene-3'-carboxylic acid allows 1 mol of phosgene to act.



  The new dye represents. a: light brown powder: Dar, Ida's cotton in a weakly alkaline bath, which has been mixed with a copper, ferrous salt solution of copper sulfate and tartrate of sodium, dyes in a washable greenish yellow shade.



  <I> Example: </I> 38.1 parts by weight of the monoazo dye from diazotized 1-amino @ -4-oxybenzene-3-oxy-5-isulphonic acid and 1-methyl-3, -amino-4-methoxybenzene are used as Na salt with the addition of 1.3.5 parts by weight of sodium acetate 'to 250 parts by weight:

          Waeser solved. This solution is at: approximately. 60 treated with 18.5 parts by weight of 3-nitrobenzoyl chloride, to which 5 parts by weight of acetone were added. You reduce that;

  Formed nitrobenzoyl product with 42 parts by weight of crystallized sodium sulfide, @ which were dissolved in 75 parts by weight of water, at 65 to 70 to the aminob: enzoyl product. The:

       Sebmedene reduction product is mixed with 25.7 (@ ewichtstealen 4-Amino-4'-oxy-1,1'-a7, above-zol-,

  3'-carboxylic acid with the addition of sodium carbonate up to a clearly alkaline reaction. dissolved in 4000 parts by weight of water and treated with phosgene for 24 hours with stirring at 30-40,

       until no more free NHZ groups can be detected. The urea derivative which has separated out is precipitated as the sodium salt, filtered and: dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn- stoffderivates, :dadurch gekennzeichnet, dass man auf 1 Mol der 2-Methyl-4-(3"-amino)- benzoylamino- 5 -methoxy-4'-oxy-l,l'-azoben- zo: PATENT CLAIM: Process for the production of a urea derivative, characterized in that 1 mol of the 2-methyl-4- (3 "-amino) - benzoylamino-5-methoxy-4'-oxy-l, l'-azoben - zo: l-3'-carbonsäure-5'-sulfonsäure und 1 Mol 4 -Amino-4'-oxy-1,1'-a.zobenzol-3'-earbousä.ure 1 Mol P'hoosg en einwirken läBt. Der neue Farbstoff stellt ein hellbraunes Pulver dar, @clas Baumwolle in schwach alha- Esehem Bade, L-3'-carboxylic acid-5'-sulfonic acid and 1 mole of 4-amino-4'-oxy-1,1'-a.zobenzene-3'-earbous acid allows 1 mole of p'hoosgen to act. The new dye is a light brown powder, @clas cotton in weak alha- Esehem Bade, das mit einer Kup@fersalzlasun- aus Kupfersulfat und weinsaurem Natrium versetzt wurde, in waschechtem grünstic.hig #J.elbem Tone anfärbt. which has been mixed with a copper salt glaze made of copper sulfate and tartrate of sodium, stains in a washable greenish yellow shade.
CH234520D 1940-11-22 1940-11-22 Process for the production of a urea derivative. CH234520A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH232121T 1940-11-22
CH234520T 1940-11-22

Publications (1)

Publication Number Publication Date
CH234520A true CH234520A (en) 1944-09-30

Family

ID=25727678

Family Applications (1)

Application Number Title Priority Date Filing Date
CH234520D CH234520A (en) 1940-11-22 1940-11-22 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH234520A (en)

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