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CH234516A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

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Publication number
CH234516A
CH234516A CH234516DA CH234516A CH 234516 A CH234516 A CH 234516A CH 234516D A CH234516D A CH 234516DA CH 234516 A CH234516 A CH 234516A
Authority
CH
Switzerland
Prior art keywords
amino
production
oxy
weight
parts
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 CH234516A publication Critical patent/CH234516A/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

  

      Zusatzpatent    zum Hauptpatent Nr. 232121.    Verfahren zur Herstellung eines     Harnstoffderivates.       Es     wurde        gefunden;,        da,Z        man    zu     einem          neuen        Harnstof    f     derivat        gelangt,    das gleich  zeitig     einen        wertvollen        Azofarbstoff    darstellt,  wenn     mann    auf 1     Mol        der        2-Methyl-4-,

  (4"-          amino)        -benzoylanvuso,-5-metho@xy-4'-oxy-1,1'-          azobenzol-3'-carbo@nsäure-5'-sulfon;säure    und  1     Mol        4-(4"-Amino)-b@enz.oylamino,-4'-oxy-          1,1'-azobenzal-3'-carbo#nsäiure    1     Mol        Phosgen     einwirken     lässt.     



  Der neue Farbstoff stellt     ein,    hellbraunes  Pulver dar, das     Baumwolle    in schwach alka  lischem     Bade"da@s    mit einer     Kupfersalzlösung     aus     Kupfersulfat    und     weinsaurem        Natrium          versetzt    wurde, in     waschechtem        ;grüns:tichig     gelbem     Tone    ;anfärbt.

           Beispiel:       38,1     Gewichtsteile    des     MonoazoTarbstoffes     aus     @diazotierter        1-Amino-4-oxybenzal-3-carb-          oxy-5@sulfo@nsäure    und     1-Methyl-3-amino-4-          methoxybernzal        werden:    als     Na-Salz        unter    Zu  satz von 13,5     Gewichtsteilen        Natriumacetat     in 250 Gewichtsteilen "Wasser gelöst.

   Diese  Lösung wird bei etwa 60      mit        18.,5    Gewichts-         teilen        4-Nit:robenzoy        lchlorid,    die mit 5 Ge  wichtsteilen     Aceton        versetzt        wurden:

  ,        behan-          delt.    Man     reduziert    das     gebildete        Nitro-          benzoylpro,dukt    mit 42 Gewichtsteilen kri  stallisiertem     Natriumsulfid,        die    in 75     Ge-          wichtsteilen    Wasser gelöst     wurden,    bei 65 bis  70  zum     Aminob,enzoylpradukt.    Das abge  schiedene     Reduktionsprodukt    wird mit 37,6       Gewichtsteilen        4-(4"-Amino)-benzoylamino-          4'-o#xy-1,

  1-azoben-zol-3'-oarbo#nsäure    unter Zu  satz von     Natriumcarbonat    bis zur     deutlichen          alkalischen    Reaktion in 4000 Gewichtsteilen       Wasis:eT        .gelöst    und     während    24     ,Stunden        unter     Rühmen bei     30=.40         mit        Phosgen    behandelt,  bis sich keine     freie        NH2-Gruppe    mehr nach  weisen     läss't.        Dass        :

  ausgeschiedene        unsymme-          trische        Harnstoffderivat    wird als     Natrium-          salz    gefällt, filtriert und     getrocknet.  



      Additional patent to main patent no. 232121. Process for the production of a urea derivative. It has been found that, Z one arrives at a new urea derivative, which at the same time represents a valuable azo dye, if one mole of the 2-methyl-4-,

  (4 "- amino) -benzoylanvuso, -5-metho @ xy-4'-oxy-1,1'-azobenzene-3'-carbo @ nic acid-5'-sulfonic acid and 1 mol 4- (4" - Amino) -b @ enz.oylamino, -4'-oxy-1,1'-azobenzal-3'-carbonic acid allows 1 mol of phosgene to act.



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

           Example: 38.1 parts by weight of the monoazo dye from @diazotized 1-amino-4-oxybenzal-3-carbo-oxy-5 @ sulfonic acid and 1-methyl-3-amino-4-methoxybenzal are: as Na salt under Zu set of 13.5 parts by weight of sodium acetate dissolved in 250 parts by weight of water.

   This solution is at about 60 with 18., 5 parts by weight of 4-Nit: robenzoy lchloride, to which 5 parts by weight of acetone were added:

  , treated. The nitrobenzoyl product formed is reduced 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 aminobenzoyl product. The separated reduction product is mixed with 37.6 parts by weight of 4- (4 "-amino) -benzoylamino-4'-o # xy-1,

  1-azoben-zol-3'-oaronic acid with the addition of sodium carbonate until a distinct alkaline reaction was found in 4000 parts by weight of Wasis: dissolved and treated with phosgene for 24 hours while stirring at 30 = .40 until no free NH2 group allows more evidence. That:

  The unsymmetrical urea derivative precipitated is precipitated as sodium salt, filtered and dried.

Claims (1)

PATENTANSPRUCH: VerfaliTen zur Herstellung eines Ilarn- sto@ffderivates:,dadurch :gek-ennzeichmet, dass man auf 1 Mol der 2-Methyl-4-(4"-amino)- 9 b@enzoylamin; PATENT CLAIM: Processes for the production of an Ilarnsto @ ffderivates:, characterized by: marked that one mole of 2-methyl-4- (4 "-amino) - 9 b @ enzoylamine; a- 5 -n#etho@xy-4'-oxy-1,1'-azoben- zol-3'-carbonsäure-5'-sulfonsäure und 1 Mol 4-(4"-Amino)- b@enzoylamim@o@-4'- oxy -1,1'-azo- benzol-3'-carbonsäure 1 Mol P'hosigen, einwir ken lä.Bt. Der neue Farbstoff stellt ein: hellbraunes Pulver :dar, @da: a- 5 -n # etho @ xy-4'-oxy-1,1'-azoben- zene-3'-carboxylic acid-5'-sulfonic acid and 1 mole 4- (4 "-amino) - b @ enzoylamim @ o @ -4'- oxy -1,1'-azo-benzene-3'-carboxylic acid 1 mol P'hosigen, can work in. The new dye is a: light brown powder: is, @da: s Baumwolle rin schwach alka- lischem Bade, das mit einer Kupfersalzlösung aus: Kupfersulfat und weintsaurem Natrium versetzt wurde, in waschechtem grünstichig gelbem Tone anfärbt. s Cotton in a weakly alkaline bath to which a copper salt solution made from: copper sulphate and tartaric acid is dyed in a washable, greenish yellow shade.
CH234516D 1940-11-22 1940-11-22 Process for the production of a urea derivative. CH234516A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH234516T 1940-11-22
CH232121T 1940-11-22

Publications (1)

Publication Number Publication Date
CH234516A true CH234516A (en) 1944-09-30

Family

ID=25727674

Family Applications (1)

Application Number Title Priority Date Filing Date
CH234516D CH234516A (en) 1940-11-22 1940-11-22 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH234516A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921225C (en) * 1951-06-11 1954-12-13 Ciba Geigy Process for the preparation of disazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921225C (en) * 1951-06-11 1954-12-13 Ciba Geigy Process for the preparation of disazo dyes

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