CH293607A - Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 '). - Google Patents

Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 ').

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Publication number
CH293607A
CH293607A CH293607DA CH293607A CH 293607 A CH293607 A CH 293607A CH 293607D A CH293607D A CH 293607DA CH 293607 A CH293607 A CH 293607A
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CH
Switzerland
Prior art keywords
stilbene
amino
disodium salt
diamino
mol
Prior art date
Application number
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German (de)
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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 CH293607A publication Critical patent/CH293607A/en

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Description

  

      Verfahren        zur        Herstellung    eines Derivates der     4,4'-Diamino-stilben-disulfonsäure-(2,2').       Es wurde gefunden, dass man zu einem  neuen Derivat der     4,4'-Diamino-stilben-disul-          fonsäure-(2,2')    gelangt, wenn man auf 1     Mol     des     Dinatriumsalzes    der     4-Amino-4'-[2-anilido-          4-        (fl-oxyäthylamino)    -1, 3,     5-triazyl    - (6) -     amino    ]     -          stilben-disulfonsäure-(2,2'),

      hergestellt durch  Kondensation von 1     Mol        Cyanurehlorid    mit.  1     Mol    des     Dinatriumsalzes    der     4-1Titro-4'-          amino-stilben-disulfonsäure-(2,2'),    1     Mol    Mono-         äthanolamin    und 1 -.Hol Anilin und anschlie  ssende Reduktion des Nitrokörpers zum Amin,  1.     Mol        3,4,5-Trimethoxy-benzoylchlorid    einwir  ken lässt.  



  Das so erhaltene neue     Dinatriumsalz    der  4-[ (3,4,5 -     Trimethoxy-        benzoyl)    -     amino]    - 4'-     [2-          anilido    - 4 -     (ss-oxy        äthylamino)        -1,3,5-triazyl-    (6)     -          amino]-stilben-disulfonsäure-(2,2')    der Formel  
EMI0001.0037     
    stellt ein hellgelbes Pulver dar, welches in  Wasser löslich ist.

   Es kann als optisches  Bleichmittel verwendet werden.     Cellulosemate-          rial,    das mit einer solchen Lösung behandelt  worden ist, fluoresziert im ultravioletten  Licht bläulich.  



  <I>Beispiel:</I>  Durch     Kondensation    von 1     Mol        Cyanur-          chlorid    mit 1     Mol    des     Dinatriumsalzes    der       4-Nitro-4'-amino-stilben-disulfonsäure-(2,2'),     1     Mol        Monoäthanolamin    und 1     Mol    Anilin und    anschliessende Reduktion stellt man zuerst die  4 -     Amino    - 4' - [ 2 -     anilido    - 4-     (p-oxyäthylamino)        -          1,3,5-triazyl-   <B>(6)

  </B> -     amino    ] -     stilben-disulfonsäure-          (2,2')    her.  



  30 Teile dieses Produktes werden mit 250       Teilen        50        %        igem        Aceton        verrührt        und        mit          Natriumhydroxyd    neutralisiert. Zu der erhal  tenen Lösung gibt man innerhalb von einer  Stunde bei 10 bis 15  unter Aufrechterhal  tung einer schwach alkalischen Reaktion 18  Teile     3,4,5-Trimethoxybenzoylchlorid    hinzu.

        Sobald das Ausgangsmaterial     verschwunden     ist, destilliert man die Hauptmenge des Ace  tons im Vakuum bei niedriger Temperatur ab,  fügt zu dem Rückstand wässerige Natrium  chloridlösung hinzu, kühlt auf Raumtempera  tur ab, filtriert das abgeschiedene Kondensa  tionsprodukt, wäscht es mit     Natriumchlorid-          lösung    und trocknet.

   Das so erhaltene     Di-          natriumsalz    der 4- [     (3,4,5-Trimethoxy-ben-          zoyl)        -amino]    - 4' -     [2-anilido-4    -     (ss-oxyäthyl-          amino        )-1,3,5-triazyl    -<B>(6)</B> -     amino]        -stilben-disul-          fonsäure-(2,2')    bildet ein hellgelbes, in Was  ser lösliches Pulver.



      Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 '). It has been found that a new derivative of 4,4'-diamino-stilbene-disulphonic acid- (2,2 ') is obtained if one mole of the disodium salt of 4-amino-4' - [2- anilido- 4- (fl-oxyäthylamino) -1, 3, 5-triazyl - (6) - amino] - stilbene-disulfonic acid- (2,2 '),

      produced by condensation of 1 mole of cyanuric chloride with. 1 mol of the disodium salt of 4-1-nitro-4'-amino-stilbene-disulfonic acid- (2,2 '), 1 mol of monoethanolamine and 1-hol aniline and subsequent reduction of the nitro body to the amine, 1st mol 3, 4,5-trimethoxy-benzoyl chloride can act.



  The new disodium salt of 4- [(3,4,5 - trimethoxybenzoyl) - amino] - 4'- [2- anilido - 4 - (ss-oxy äthylamino) -1,3,5-triazyl- ( 6) amino] stilbene disulfonic acid (2,2 ') of the formula
EMI0001.0037
    represents a light yellow powder which is soluble in water.

   It can be used as an optical bleach. Cellulose material that has been treated with such a solution fluoresces bluish in ultraviolet light.



  <I> Example: </I> By condensation of 1 mole of cyanuric chloride with 1 mole of the disodium salt of 4-nitro-4'-amino-stilbene-disulfonic acid- (2.2 '), 1 mole of monoethanolamine and 1 mole of aniline and subsequent reduction, the 4 - amino - 4 '- [2 - anilido - 4- (p-oxyäthylamino) - 1,3,5-triazyl- <B> (6)

  </B> - amino] - stilbene disulfonic acid (2.2 ').



  30 parts of this product are stirred with 250 parts of 50% strength acetone and neutralized with sodium hydroxide. 18 parts of 3,4,5-trimethoxybenzoyl chloride are added to the solution obtained over the course of one hour at 10 to 15 while maintaining a weakly alkaline reaction.

        As soon as the starting material has disappeared, the bulk of the acetone is distilled off in vacuo at low temperature, aqueous sodium chloride solution is added to the residue, the mixture is cooled to room temperature, the condensation product which has separated out is filtered off, washed with sodium chloride solution and dried.

   The disodium salt of 4- [(3,4,5-trimethoxy-benzoyl) -amino] -4 '- [2-anilido-4 - (ss-oxyethylamino) -1,3,5 obtained in this way -triazyl - <B> (6) </B> - amino] -stilbene-disulphonic acid- (2,2 ') forms a light yellow, water-soluble powder.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Derivates der 4,4'-Diamino-stilben-disi-lfon- säure-(2,2'), dadurch gekennzeichnet, dass man 1 Mol des Dinatriumsalzes der 4-Amino-4'- [ 2 - anilido - 4 - (f-oxy äthylamino) -1, 3, 5-tr iazyl- (6)-amino]-stilben-disulfonsättre-(2,2'), herge stellt durch Kondensation von 1 1lol Cvanur- chlorid mit. PATENT CLAIM: Process for the preparation of a new derivative of 4,4'-diamino-stilbene-disi-lfonic acid- (2,2 '), characterized in that 1 mol of the disodium salt of 4-amino-4'- [2 - Anilido - 4 - (f-oxy äthylamino) -1, 3, 5-triazyl- (6) -amino] -stilbene-disulfonsättre- (2,2 '), produced by condensation of 1 1lol Cvanur- chloride with . 1 llol des Dinatriumsalzes der 4-Nitro - 4'-amino-stilben-clisulfonsäure- (2,2'), 1 Mol Monoäthanolamin und 1 Mol Anilin und anschliessende Reduktion des Nitrokör- pers zum Amin, mit 1 1 1 3,4,5-Trimethoxy- benzoylchlorid umsetzt. Das neue Dinatriumsalz ist ein hellgelbes, wasserlösliches Pulver. Es kann zum opti schen Bleichen von Cellulosefasern verwendet werden. 1 llol of the disodium salt of 4-nitro-4'-amino-stilbene-clisulfonic acid- (2.2 '), 1 mol of monoethanolamine and 1 mol of aniline and subsequent reduction of the nitro body to the amine, with 1 1 1 3.4, 5-trimethoxybenzoyl chloride converts. The new disodium salt is a light yellow, water-soluble powder. It can be used for optical bleaching of cellulose fibers.
CH293607D 1949-10-28 1949-10-28 Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 '). CH293607A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH287192T 1949-10-28
CH293607T 1949-10-28

Publications (1)

Publication Number Publication Date
CH293607A true CH293607A (en) 1953-09-30

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Application Number Title Priority Date Filing Date
CH293607D CH293607A (en) 1949-10-28 1949-10-28 Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 ').

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CH (1) CH293607A (en)

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