CH197582A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH197582A
CH197582A CH197582DA CH197582A CH 197582 A CH197582 A CH 197582A CH 197582D A CH197582D A CH 197582DA CH 197582 A CH197582 A CH 197582A
Authority
CH
Switzerland
Prior art keywords
parts
phenyl
production
azo dye
dye
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 CH197582A publication Critical patent/CH197582A/en

Links

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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Azofarbstoffes.       Es     @        wurde-gefunden,    dass, man einen     neuen          Azofarbstoff    erhält,     wenn        man,das        1-Phenyl-          (-4'-phenyl-        4"-aoetylamino)-        ä        -methyl-    5     -pyr-          azolon    der Formel  
EMI0001.0015     
         mit,diazotierter        Sulfanilsäure,    vereinigt.

   Der  so erhaltene Farbstoff bildet ein orange  gelbes Pulver, das Baumwolle in gelben.  Tönen färbt.  



  Das     1-Phenyl-(4'-ph        enyl-4"-acetylamino)-          #)-methyl-5-pyrazolon    kann wie folgt     lherge-          stellt    werden:  22;6 Teile fein gemahlenes     Monoaeetyl-          ben;zidin    werden in 50 Teilen Wasser und  etwa Eis     angerührt,    mit     .30    Teilen     Salzsäure          -d    = 1,15 versetzt.

   Man tropft bei 0     bis   <B>10,'</B>  langsam eine Lösung von 7 Teilen     Natrium-          nitrit    in etwa     241        Teilen    Wasser zu und     rührt            n        ac        -h        be        endigter        ZugaAbe        des        Nitrites        nor        h     etwa 1     Stunde    und     filtriert.     



  Die     filtrierte        Diazolösung    lässt man unter       gutem        Rühren    in ein von aussen     gekühltes     Gemisch von 100 Teilen     Zinnchlorür    etwa       63%ig    und 50     Teilen        .Salzsäure    d - 1,15  bei 01 bis 5       einlaufen.     



  Das:     gebildete        Hydrazin    fällt schwer lös  lich     aus.    Man     rührt    noch etwa 12     iStunden,          nutsoht,    wäscht     mit        vemdünnter    Salzsäure  und dann mit Wasser nach.  



       Das.    so     hergestellte        Hydrazinchlorhydrat     der Formel  
EMI0001.0068     
    wird in 500 Teilen Wasser     und    100 Teilen       Salzsäure    d = 1,15 etwa     2-3    Stunden ge  kocht.     Das;        Chlorhydmat,des        4-Hydrazino-4'-          aminodiphenyls    geht in Lösung. Man     ent-          zinnt    gegebenenfalls     mit    Schwefelwasser  stoff,     filtriert    und lässt erkalten.

   Ein grosser  Teil des     C#hlo#rhydrats    fällt aus. Aus der           Mutterlauge.    kann     "eueres        Chlorhydrat    aus  gesalzen oder mit Alkalien die Base in     Fmi-          beit    gesetzt     werden.     



  Diesel letztere bildet, aus     ;llkoliol    um  kristallisiert, weisse     Kristalle    vom F. 179 ",  die sich an der Luft bräunen.  



       27,2    Teile des so hergestellten     Chlor-          hydrates    des Hydrazins werden in heissem  Wasser     a.ufgeschlemmt.    Man kondensiert mit  14     Teilen        Acetessigestür    bei etwa<B>00</B>   unter       langs.amein    Abstumpfen der     frei    der Konden  sation frei     werdenden    Säure.

       Naeli    beendig  ter Kondensation lässt man erkalten, stellt  mit     Xtza.lkali        phenolplitha,lein-alkalisch,    rührt  12 Stunden, erwärmt bis alles gelöst und  fällt das     Pyra.zolon    durch Neutralisation  aus.  



       Das    neue Produkt ist. ein weisses Pulver  vom F. 194', löslich in verdünnter Natron  lauge und verdünnten     Mineralsäuren.     



  <I>Beispiel:</I>  Man     löst   <B>30.7</B> Teile     1-Phenyl-(4'-phenyl-          4"-acetylamino)-3-methyl-5-pyra.zolon    der  Formel  
EMI0002.0027     
    in     etwa        5a(1    Teilen     Wasser,    enthaltend 10  Teile Natronlauge von     3-6                 Be    und 1-5 Teilen  Soda     calc.     



  Die     filtrierte        IxSsung    versetzt man lang  sam mit der     Diazoverbindung        aus   <B>17,5</B> Tei  len     Sulfanils@äure.        Nach        beendigter    Kupp  lung wärmt man auf, salzt aus und isoliert  den gebildeten Farbstoff wie üblich.



  Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1-phenyl- (-4'-phenyl- 4 "-aoetylamino) -α-methyl-5-pyrazolone of the formula
EMI0001.0015
         with, diazotized sulfanilic acid, combined.

   The dye thus obtained forms an orange-yellow powder, the cotton in yellow. Tones colors.



  The 1-phenyl- (4'-phenyl-4 "-acetylamino) - #) - methyl-5-pyrazolone can be prepared as follows: 22; 6 parts of finely ground monoethylbenzidine are dissolved in 50 parts of water and about ice stirred, mixed with .30 parts of hydrochloric acid -d = 1.15.

   At 0 to 10, a solution of 7 parts of sodium nitrite in about 241 parts of water is slowly added dropwise and, after the addition of the nitrite, the mixture is stirred for about 1 hour and filtered.



  The filtered diazo solution is allowed to run into an externally cooled mixture of 100 parts of about 63% tin chloride and 50 parts of hydrochloric acid d-1.15 at 01 to 5, with thorough stirring.



  The hydrazine formed is sparingly soluble. The mixture is stirred for a further 12 hours, not nuts, washed with dilute hydrochloric acid and then with water.



       The. hydrazine chlorohydrate of the formula thus prepared
EMI0001.0068
    is boiled in 500 parts of water and 100 parts of hydrochloric acid d = 1.15 for about 2-3 hours. The; Chlorhydmat, des 4-hydrazino-4'-aminodiphenyl, goes into solution. If necessary, it is detinned with hydrogen sulphide, filtered and allowed to cool.

   A large part of the C # hlo # rhydrate falls out. From the mother liquor. your chlorine hydrate can be mixed with salts or with alkalis.



  The latter forms white crystals of F. 179 ", which turn brown in the air.



       27.2 parts of the hydrazine chlorohydrate prepared in this way are suspended in hot water. The condensation is carried out with 14 parts of acetoacetic acid at about <B> 00 </B> with slow blunting of the acid released from the condensation.

       Naeli finished condensation is allowed to cool, made with Xtza.lkali phenolplitha, lineal alkaline, stirred for 12 hours, heated until everything is dissolved and the Pyra.zolon precipitates by neutralization.



       The new product is. a white powder from F. 194 ', soluble in dilute caustic soda and dilute mineral acids.



  <I> Example: </I> <B> 30.7 </B> parts of 1-phenyl- (4'-phenyl- 4 "-acetylamino) -3-methyl-5-pyra.zolone of the formula are dissolved
EMI0002.0027
    in about 5a (1 part water containing 10 parts sodium hydroxide solution of 3-6 Be and 1-5 parts soda calc.



  The filtered solution is slowly mixed with the diazo compound composed of 17.5 parts of sulfanilic acid. After coupling has ended, the mixture is warmed up, salted out and the dye formed is isolated as usual.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen lzofarbstoffes, dadurch gekennzeichnet, dass man das 1-Phenyl-(4'-phenyl--1"-acetyl- amiiio)-3-methyl-5-pyrazolon der Formel EMI0002.0047 finit diazotierter Sulfanilsäure vereinigt. Der so erhaltene Farbstoff bildet ein orange- gel@bes Pulver, ,das Baumwolle in gelben Tönen färbt. PATENT CLAIM: Process for the preparation of a new lzo dye, characterized in that 1-phenyl- (4'-phenyl-1 "-acetyl-amiiio) -3-methyl-5-pyrazolone of the formula EMI0002.0047 finitely diazotized sulfanilic acid combined. The dye thus obtained forms an orange-yellow powder, which dyes cotton in yellow shades.
CH197582D 1935-11-06 1935-11-06 Process for the production of a new azo dye. CH197582A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH197582T 1935-11-06

Publications (1)

Publication Number Publication Date
CH197582A true CH197582A (en) 1938-05-15

Family

ID=4440954

Family Applications (1)

Application Number Title Priority Date Filing Date
CH197582D CH197582A (en) 1935-11-06 1935-11-06 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH197582A (en)

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