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CH295296A - 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
CH295296A
CH295296ACH295296DACH295296ACH 295296 ACH295296 ACH 295296ACH 295296D ACH295296D ACH 295296DACH 295296 ACH295296 ACH 295296A
Authority
CH
Switzerland
Prior art keywords
stilbene
amino
disulfonic acid
diamino
derivative
Prior art date
Application number
Other languages
German (de)
Inventor
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 GeigyfiledCriticalCiba Geigy
Publication of CH295296ApublicationCriticalpatent/CH295296A/en

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Translated fromGerman

      Verfahren    zur Herstellung eines Derivates der     4,4'-Diamino-stilhen-disulfonsäure-(2,2').       Es wurde gefunden,     dass    man zu einem  neuen Derivat der     4,4'-Diamino-stilben-disul-          fonsäi-ire-(2,2')    gelangt, wenn man 1     11Tol    des       Dinatritunsalzes    der     4-[(p-11Methoxy-benzoyl)-          amino]    -4'-     [2-chlor-4,-methylamino-1,3,5-tri-          azyl-    (6)     -amino]        -stilben-disulfonsäure-    (2,2')    mit 1     Mol        Thiophenol    umsetzt.    Die Umsetzung kann z. B. in neutraler bis  schwach     alkalischer        Lösung    bei 70-75  C       vorgenommen        werden.       Das so erhaltene neue     Dinatriumsalz    der  4-[     (p-Methoxy-benzoyl)-amino]-4'-[?        phenyl-          thio-4-methylamino-1,3,5-triazyl-   <B>(6)</B>     -amino]        -          stilben-disulfonsäure-(2,2')    der Formel  EMI0001.0027         bildet ein wasserlösliches Pulver,     dessen    Lö  sungen im     -ultravioletten    Licht bläulich fluo  reszieren. Es kann     ztun    optischen Bleichen  von     Zellulosefasern    verwendet werden.         Beispiel:          Zn    einer feinen, durch Eingiessen von 3,8  Teilen in Aceton gelöstem     Cyanurchlorid    in       Eiswasser    erhaltenen     Suspension    gibt man  bei 0-5  C eine     Lösung    von 11 Teilen des     Di-          rtatritunsalzes    der 4-[     (p-Methoxy-benzoyl)-          amino]        -4'-amino-stilben-disulfonsäure-    (2,2')  in 200 Teilen     Wasser,      wobei die     Reaktions-          masse    durch     Zutropfen    einer Lösung von  1,1 Teilen     Natriumcarbonat    in 10 Teilen       Wasser    stets schwach sauer bis neutral gehal  ten wird.   Sobald das Ausgangsmaterial     ver-          sehwunden    ist, werden 1,6 Teile     40 /oige            wässerige        Monomethylaminlösung    zugefügt,       Clie        Reaktionstemperatur    auf 30-35  C ge  steigert, 4     Stunden    so gehalten     und    die ent  stehende     Salzsäure    durch     allmähliches    Zu  geben von     etwa    1,  0 Teil in 10 Teilen Wasser  gelöstem     Natriumearbonat        neutralisiert.    Hier  auf fügt man unter gleichzeitiger Steigerung  der Temperatur auf 70-75  C 2,2 Teile     Thio-          phenol    zu dem Reaktionsgemisch     und    hält  dasselbe durch     allmähliche    Zugabe von 0,8       Teilen    in 20 Teilen     Wasser    gelöstem     Na-          triumhydroxyd    neutral     bis    schwach     alkalisch.     Nach     Beendigung    der     Reaktion    wird erkalten  gelassen,   das     entstandene    Kondensationspro  dukt durch Zugabe von     Natriumchlorid    ab  geschieden, filtriert, mit     Natriumchlorid-          lösung    gewaschen und getrocknet. Die neue  Verbindung stellt ein helles, wasserlösliches      Pulver dar. Seine     Lösungen    fluoreszieren im  ultravioletten Lichte bläulich.      Process for the preparation of a derivative of 4,4'-diamino-stilhen-disulfonic acid- (2,2 '). It has been found that a new derivative of 4,4'-diamino-stilbene-disulphonsäi-ire- (2,2 ') is obtained if 1 11 tol of the dinatrite salt of 4 - [(p-11-methoxy-benzoyl ) - amino] -4'- [2-chloro-4, -methylamino-1,3,5-triacyl- (6) -amino] -stilbene-disulfonic acid- (2,2 ')    with 1 mole of thiophenol. The implementation can e.g. B. can be made in neutral to slightly alkaline solution at 70-75 C.  The new disodium salt of 4- [(p-methoxy-benzoyl) -amino] -4 '- [? phenylthio-4-methylamino-1,3,5-triazyl- <B> (6) </B> -amino] - stilbene-disulfonic acid- (2,2 ') of the formulaEMI0001.0027    forms a water-soluble powder, the solutions of which resce bluish fluo in ultraviolet light. It can be used for optical bleaching of cellulose fibers.       Example: To a fine suspension obtained by pouring 3.8 parts of cyanuric chloride dissolved in acetone into ice water, a solution of 11 parts of the di-rtatrite salt of 4- [(p-methoxy-benzoyl) -amino is added at 0-5 ° C. ] -4'-amino-stilbene-disulfonic acid- (2.2 ') in 200 parts of water,      the reaction mass being kept slightly acidic to neutral by adding dropwise a solution of 1.1 parts of sodium carbonate in 10 parts of water.   As soon as the starting material has disappeared, 1.6 parts of 40% aqueous monomethylamine solution are added, the reaction temperature is increased to 30-35 C and held for 4 hours, and the resulting hydrochloric acid is gradually added by adding about 1,  0 part of sodium carbonate dissolved in 10 parts of water was neutralized. At this point, while increasing the temperature to 70-75 ° C., 2.2 parts of thiophenol are added to the reaction mixture and the same is kept neutral to slightly alkaline by the gradual addition of 0.8 parts of sodium hydroxide dissolved in 20 parts of water. After the reaction has ended, it is allowed to cool,   the condensation product formed is separated off by the addition of sodium chloride, filtered, washed with sodium chloride solution and dried. The new compound is a light, water-soluble powder. Its solutions fluoresce bluish in ultraviolet light.

Claims (1)

Translated fromGerman
PATENTANSPRUCH: Verfahren zur Herstellung eines neuen De rivates der 4,4'-Diamino-stilben-disulfonsäure- (2,2'), dadurch gekennzeichnet, dass 1 Mol des Dinatriumsalzes der 4 - [ (p - Methoxy- b enzoyl) - amino] - 4' - [2-chlor-4-methylamino- 1,3,5-triazyl- (6) -amino] -stilben-disulfonsäure- (2,2')PATENT CLAIM: A process for the production of a new derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 '), characterized in that 1 mol of the disodium salt of 4 - [(p - methoxybenzoyl) - amino ] - 4 '- [2-chloro-4-methylamino-1,3,5-triazyl- (6) -amino] -stilbene-disulfonic acid- (2,2') mit 1 Mol Thiophenol umgesetzt wird. Das neue Dinatriumsalz der 4-[ (p-Meth- oxy - benzoyl) - amino] - 4'- [2 - phenyl - thio -4- nr.ethylamino-1,3,5-triazyl-(6)-amino] stilben- disizlfonsäure-(2,2') ist ein helles Pulver, is reacted with 1 mole of thiophenol. The new disodium salt of 4- [(p-methoxy - benzoyl) - amino] - 4'- [2 - phenyl - thio -4- nr.ethylamino-1,3,5-triazyl- (6) -amino] stilbene disizlfonic acid (2.2 ') is a light-colored powder, das in Wasser löslich ist und zum optischen Blei chen von Zellulosefasern verwendet werden kann. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, :dass man die Umsetzung in neutraler bis schwach alkalischer Lösung bei 70-75 C vornimmt. which is soluble in water and can be used for optical leading of cellulose fibers. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that: the reaction is carried out in a neutral to slightly alkaline solution at 70-75 ° C.
CH295296D1949-10-281949-10-28 Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 ').CH295296A (en)

Applications Claiming Priority (2)

Application NumberPriority DateFiling DateTitle
CH291791T1949-10-28
CH295296T1949-10-28

Publications (1)

Publication NumberPublication Date
CH295296Atrue CH295296A (en)1953-12-15

Family

ID=25733139

Family Applications (1)

Application NumberTitlePriority DateFiling Date
CH295296DCH295296A (en)1949-10-281949-10-28 Process for the preparation of a derivative of 4,4'-diamino-stilbene-disulfonic acid- (2,2 ').

Country Status (1)

CountryLink
CH (1)CH295296A (en)

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