CH166075A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH166075A
CH166075A CH166075DA CH166075A CH 166075 A CH166075 A CH 166075A CH 166075D A CH166075D A CH 166075DA CH 166075 A CH166075 A CH 166075A
Authority
CH
Switzerland
Prior art keywords
parts
production
azo dye
methoxy
new azo
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 CH166075A publication Critical patent/CH166075A/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
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    der Formel  
EMI0001.0003     
    erhält,     \wenn    man das     4'-Methoxy-4-diazo-          triphenylamin    mit dem m -     Nitranilid    der  2.     3-Oxynaphthoesäure        kuppelt..     



  Der so erhaltene Farbstoff bildet ein  blaues Pulver. Auf geeigneten Substraten,  wie zum Beispiel Baumwolle, Wolle, Kunst  seide, hergestellt, färbt es diese in reinen,       :ehr    echten blauen Tönen.    <I>Beispiel:</I>  39 Teile     4'-Methoxy-4-aminotriphenyl-          amin    werden wie üblich     diazotiert    und in    eine Lösung von 30,8 Teilen des     m-Nitra-          nilids    der 2.     3-Oxynaphthoesäure,    60 Teilen  30%iger     Natriumhydroxydlösung,    15 Teilen  Soda und 2000 Teilen Wasser eingetragen.  Der gebildete Farbstoff fällt sofort aus. Er  wird filtriert, gewaschen und getrocknet.  



  Das     4'-Methoxy    - 4 -     aminotriphenylamin     kann wie folgt dargestellt werden:  121,5 Teile     4'-Methoxydiphenylamin-2-          ca.rbonsäure,    F. 184 bis 18-5  , 187,5 Teile       p-Nitrojodbenzol,    80 Teile     Kaliumkarbonat     (wasserfrei), 375 Teile Nitrobenzol und  5 Teile Naturkupfer C werden während einer  Stunde bei 195 bis<B>9-00'</B> im Ölbad erwärmt.  Das Nitrobenzol und das überschüssige     p-Ni-          trojodbenzol    werden mit Wasserdampf ab  getrieben.

   Es bleibt eine braunrote Lösung,  aus der man mit Salzsäure die     4"-Methoxy-          4'-nitrodiphenylamino-2-carbonsäure    als gel  ben Niederschlag abscheidet, zurück. Durch  Kristallisieren aus Eisessig erhält man den  Körper in orangegelben     Blättchen,    F. 162  bis 163  .      100 Teile     4"-Methoxy-4'-nitrotriphenyl-          amin-2-carbonsäure,    250 Teile Nitrobenzol,  5 Teile Naturkupfer C werden während 4 bis  5     Stunden    unter     Rückfluss    erhitzt. Das     Nitro-          benzol    wird mit Wasserdampf abgetrieben.

    Es bleibt ein in der     gälte    erstarrendes     0l     zurück. Durch Kristallisation aus Eisessig  erhält man das     4'-Methoxy-4-nitrotriphenyl-          amin    in orangegelben Blättchen F. P. 110 bis  111  . Durch Reduktion mit Eisen und Salz  säure in Alkohol erhält man das     V-Methoxy-          4-aminotriphenylamin    als farblose Nadeln  vom F. 107 bis<B>108'.</B>



  Process for the production of a new azo dye. It has been found that a new azo dye of the formula
EMI0001.0003
    obtained \ if the 4'-methoxy-4-diazo-triphenylamine is coupled with the m -nitranilide of the 2. 3-oxynaphthoic acid ..



  The dye thus obtained forms a blue powder. Produced on suitable substrates, such as cotton, wool, artificial silk, it colors them in pure, real blue tones. <I> Example: </I> 39 parts of 4'-methoxy-4-aminotriphenylamine are diazotized as usual and converted into a solution of 30.8 parts of the m-nitrilide of 2, 3-oxynaphthoic acid, 60 parts of 30 % sodium hydroxide solution, 15 parts of soda and 2000 parts of water entered. The dye formed precipitates immediately. It is filtered, washed and dried.



  The 4'-methoxy - 4 - aminotriphenylamine can be represented as follows: 121.5 parts of 4'-methoxydiphenylamine-2-carboxylic acid, F. 184 to 18-5, 187.5 parts of p-nitroiodobenzene, 80 parts of potassium carbonate ( anhydrous), 375 parts of nitrobenzene and 5 parts of natural copper C are heated in an oil bath at 195 to 9-00 'for one hour. The nitrobenzene and the excess p-nitroiodobenzene are driven off with steam.

   A brown-red solution remains, from which the 4 "-methoxy-4'-nitrodiphenylamino-2-carboxylic acid is separated out as a yellow precipitate with hydrochloric acid. Crystallization from glacial acetic acid gives the body in orange-yellow leaves, mp 162-163 100 parts of 4 "-methoxy-4'-nitrotriphenylamine-2-carboxylic acid, 250 parts of nitrobenzene, 5 parts of natural copper C are refluxed for 4 to 5 hours. The nitrobenzene is driven off with steam.

    There remains an oil that solidifies in the cold. Crystallization from glacial acetic acid gives 4'-methoxy-4-nitrotriphenylamine in orange-yellow leaves F.P. 110 to 111. Reduction with iron and hydrochloric acid in alcohol gives V-methoxy-4-aminotriphenylamine as colorless needles from F. 107 to <B> 108 '. </B>

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azo- farbstoffes der Formel EMI0002.0016 dadurch gekennzeichnet, dass man das 4'-Me- thoxy-4-diazotriphenylamin mit dein m-Ni- tranilid der 2 . 8-Oxynaphthoesäure kuppelt. Auf geeigneten Substraten, wie zum Beispiel Baumwolle, Wolle. Kunstseide, hergestellt, färbt er diese in reinen. sehr echten blauen Tönen. PATENT CLAIM: Process for the production of an azo dye of the formula EMI0002.0016 characterized in that the 4'-methoxy-4-diazotriphenylamine with the m-nitranilide of the 2. 8-oxynaphthoic acid couples. On suitable substrates such as cotton, wool. Artificial silk, produced, he dyes these in pure. very real blue tones.
CH166075D 1932-07-13 1932-07-13 Process for the production of a new azo dye. CH166075A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH163540T 1932-07-13
CH166075T 1932-07-13

Publications (1)

Publication Number Publication Date
CH166075A true CH166075A (en) 1933-12-15

Family

ID=25717792

Family Applications (1)

Application Number Title Priority Date Filing Date
CH166075D CH166075A (en) 1932-07-13 1932-07-13 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH166075A (en)

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