CH293608A - 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
CH293608A
CH293608A CH293608DA CH293608A CH 293608 A CH293608 A CH 293608A CH 293608D A CH293608D A CH 293608DA CH 293608 A CH293608 A CH 293608A
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CH
Switzerland
Prior art keywords
sep
stilbene
disulfonic acid
amino
disodium salt
Prior art date
Application number
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German (de)
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Aktiengesellschaft Ciba
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Ciba Geigy
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Publication date
Application filed by Ciba Geigy filed Critical Ciba Geigy
Publication of CH293608A publication Critical patent/CH293608A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Description

  

  Verfahren     zur    Herstellung eines Derivates der     4,4'-Diamino-atilhen-disulfonsäure-(2,2').       Es wurde gefunden, dass man zu einem  neuen Derivat der     4,4'-Dia.mino-stilben-disul-          fonsäure-(2,2')    gelangt, wenn man 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     11o1        Cvanurchlorid    mit  1     11o1    des     Dinatriumsalzes    der     4-Nitro-4'-          amino-stilben-(lisulfonsäure-(2,2'),    1     llol    llono-  
EMI0001.0021     
    stellt ein hellgelbes, wasserlösliches Pulver  dar und kann als optisches Bleichmittel für       Cellulosefasern    verwendet werden.  



  <I>Beispiel:</I>  Durch     Kondensation    von 1.     Mol        Cyanur-          chlorid    mit 1     Mol    des     Dinatriumsalzes    der       4--        Nitro-    4'-     aznino-stil.ben-disulfonsäure-    (2,2'),  1     Mol        Monoäthanolamin    und 1     Mol    Anilin und  anschliessende Reduktion stellt.

   man zuerst die  4 -     Amino    -     4'-    [2 -     anilido    - 4-     (ss-oxyäthylamino)        -          1,3,5-triazyl    - (6)     -amino    ]     -stilben-disulfonsäure-          (2,2')    her.         äthanolamin    und 1     Mol    Anilin und anschlie  ssende Reduktion des     Nitrokörpers    zum Amin,  mit. 1     Mol        3-llethyl-4-methoxybenzoylchlor        id     umsetzt.  



  Das so erhaltene neue     Dinatriumsalz    der  4-[     (3-Methyl-4-methoxy-benzoyl)-amino]-4'-          [    2 -     anilido    - 4 -     (ss-oxyäthylamino        )-1,3,5-triazyl-          (6)        -amino]        -stilben-disulfonsäure-    (2,2')

   der  Formel    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 Aufrechterhaltung  einer schwach alkalischen Reaktion 8,5 Teile       3-llethyl-4-methoxy-benzoylehlorid    hinzu.

   So  bald das Ausgangsmaterial verschwunden ist,  destilliert man die Hauptmenge des Acetons  im Vakuum bei niedriger Temperatur ab,     fügt     zu dem Rückstand wässerige     Natriumehlorid-          lösung    hinzu, kühlt, auf Raumtemperatur ab,  filtriert das abgeschiedene Kondensationspro-      Bukt, wäscht es mit     Natriumchloridlösung    und  trocknet.  



  Das so erhaltene     Dinatriumsalz    der 4-[     (3-          Metliyl    - 4 -     methoxy-benzoyl)        -amino)    - 4'- [     2-ani-          lido-4-        (ss-oxyäthylamino)        -1,3,5-triazyl-        (6)-          ainino]-stilben-distilfonsä.ure-(2,2')    bildet ein  Hellgelbes Pulver, das in Wasser löslich ist.



  Process for the preparation of a derivative of 4,4'-diamino-atilhen-disulfonic acid- (2,2 '). It has been found that a new derivative of 4,4'-dia.mino-stilbene-disulphonic acid- (2,2 ') is obtained if 1 mol 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 11o1 cvanuric chloride with 1 11o1 of the disodium salt of 4-nitro-4'-amino-stilbene- (lisulfonic acid- (2.2 '), 1 llol llono-
EMI0001.0021
    is a light yellow, water-soluble powder and can be used as an optical bleaching agent for cellulose fibers.



  <I> Example: </I> By condensation of 1st mole of cyanuric chloride with 1 mole of the disodium salt of 4-nitro-4'-aznino-stil.ben-disulfonic acid- (2.2 '), 1 mole monoethanolamine and 1 mole of aniline and subsequent reduction.

   the 4 - amino - 4'- [2 - anilido - 4- (ss-oxyäthylamino) - 1,3,5-triazyl- (6) -amino] -stilbene-disulfonic acid- (2,2 ') are produced. ethanolamine and 1 mol of aniline and subsequent reduction of the nitro body to the amine, with. 1 mol of 3-llethyl-4-methoxybenzoylchloride reacted.



  The new disodium salt of 4- [(3-methyl-4-methoxy-benzoyl) -amino] -4'- [2-anilido-4 - (s-oxyäthylamino) -1,3,5-triazyl- (6 ) -amino] -stilbene-disulfonic acid- (2,2 ')

   of the formula 30 parts of this product are mixed with 250 parts of 50% strength acetone and neutralized with sodium hydroxide. 8.5 parts of 3-llethyl-4-methoxy-benzoylechloride are added to the obtained solution 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-methyl-4-methoxy-benzoyl) -amino) -4'- [2-anilido-4- (s-oxyäthylamino) -1,3,5-triazyl- ( 6) - ainino] -stilbene-distilfonsä.ure- (2,2 ') forms a light yellow powder which is soluble in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Derivates der 4,4'-Dia.mino-stilben-disulfon- säure-(2,2'), dadurch gekennzeichnet, dass man 1 1M1 des Dinatriumsalzes der 4-Amino-4'- EMI0002.0017 [ <SEP> 2 <SEP> -anilido-4-(f-oxy <SEP> äthylaiiiino <SEP> )-1,3,5-triazvl (6)-ainino]-stilben-disitlfonsäui-e-(2,?'), <SEP> her(re stellt <SEP> durch <SEP> Kondensation <SEP> von <SEP> 1. PATENT CLAIM: Process for the preparation of a new derivative of 4,4'-dia.mino-stilbene-disulfonic acid- (2,2 '), characterized in that 1 1M1 of the disodium salt of 4-amino-4'- EMI0002.0017 [<SEP> 2 <SEP> -anilido-4- (f-oxy <SEP> äthylaiiiino <SEP>) -1,3,5-triazvl (6) -ainino] -stilbene-disitlfonsäui-e- (2 ,? '), <SEP> (re creates <SEP> through <SEP> condensation <SEP> of <SEP> 1. <SEP> 11o1 <SEP> Cvanur chlorid <SEP> mit <SEP> 1 <SEP> 11o1 <SEP> des <SEP> Dinatriumsalzes <SEP> der <tb> 4 <SEP> - <SEP> N <SEP> itro <SEP> - <SEP> 4' <SEP> - <SEP> amino-stilben-disulfonsäure- <SEP> (2, <SEP> 2') <SEP> , <tb> 1 <SEP> 11o1 <SEP> Monoätlianolamin <SEP> und <SEP> 1 <SEP> 11o1 <SEP> Anilin <SEP> und <tb> anschliessende <SEP> Reduktion <SEP> des <SEP> Nitrokörpers <tb> zum <SEP> Amin, <SEP> mit <SEP> 1 <SEP> 11o1 <SEP> 3-llethyl-4-methoxy benzoylchlorid <SEP> umsetzt. <tb> Das <SEP> neue <SEP> Dinatriumsalz <SEP> ist. <SEP> ein <SEP> hellgelbes, <tb> wasserlösliehes <SEP> Pulver. <SEP> Es <SEP> kann <SEP> zum <SEP> optischen <tb> Bleichen <SEP> von <SEP> Cellulosefasern <SEP> verwendet <SEP> wer den. <SEP> 11o1 <SEP> Cvanur chloride <SEP> with <SEP> 1 <SEP> 11o1 <SEP> of the <SEP> disodium salt <SEP> of <tb> 4 <SEP> - <SEP> N <SEP> itro <SEP> - <SEP> 4 '<SEP> - <SEP> amino-stilbene-disulfonic acid- <SEP> (2, <SEP> 2') <SEP>, <tb> 1 <SEP> 11o1 <SEP> Monoätlianolamine <SEP> and <SEP> 1 <SEP> 11o1 <SEP> aniline <SEP> and <tb> subsequent <SEP> reduction <SEP> of the <SEP> nitro body <tb> to <SEP> amine, <SEP> with <SEP> 1 <SEP> 11o1 <SEP> 3-llethyl-4-methoxybenzoyl chloride <SEP>. <tb> The <SEP> is the new <SEP> disodium salt <SEP>. <SEP> a <SEP> light yellow, <tb> water-soluble <SEP> powder. <SEP> It <SEP> can <SEP> to <SEP> optical <tb> Bleaching <SEP> of <SEP> cellulose fibers <SEP> <SEP> are used.
CH293608D 1949-10-28 1949-10-28 Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 '). CH293608A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH287192T 1949-10-28
CH293608T 1949-10-28

Publications (1)

Publication Number Publication Date
CH293608A true CH293608A (en) 1953-09-30

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CH293608D CH293608A (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) CH293608A (en)

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