CH166077A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH166077A
CH166077A CH166077DA CH166077A CH 166077 A CH166077 A CH 166077A CH 166077D A CH166077D A CH 166077DA CH 166077 A CH166077 A CH 166077A
Authority
CH
Switzerland
Prior art keywords
parts
production
azo dye
diethoxy
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 CH166077A publication Critical patent/CH166077A/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)

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 163540.         Verfahren    zur Herstellung eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    der Formel  
EMI0001.0004     
    erhält, wenn man das 2'.     5'-Diäthoxy-4-cli-          azotripheiiylamin    mit dem     m-Chloranilid    der  .     3-Oxynaphthoesäure    kuppelt.  



  Der so erhaltene Farbstoff bildet ein  blaues Pulver, auf geeigneten Substraten, wie  zum Beispiel Baumwolle, Wolle, Kunstseide,  hergestellt, färbt es diese in reinen, sehr  echten blauen Tönen.  



  <I>Beispiel:</I>  34.8     '.feile    2'.     5'-Diäthoxy-4-aminotriphe-          nylamin    werden wie     üblich        diazotiert    und in         eine    Lösung von 29,7 Teilen des     m-Chlor-          anilids    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 2' .     5'-Diäthoxy    - 4 -     aminotriphenyl-          amin    kann wie folgt dargestellt werden:  150 Teile 2'.     5'-Diäthoxytriphenylamin-          2-carbonsäure,    F. 170 bis 171  , 187,5 Teile       p-Nitrojodbenzol,        .80    Teile     Kaliumkarbonat,     375 Teile Nitrobenzol und 5 Teile Natur  kupfer C werden     während    einer Stunde bei  <B>195</B> bis 200' im Ölbad erwärmt.

   Das     Nitro-          benzol    und das überschüssige     p-Nitrojodben-          zol    werden mit Wasserdampf abgetrieben.  Es bleibt eine braunrote Lösung, aus der man  mit Salzsäure die 2".     5"-Diäthoxy-4'-nitro-          triphenylamin-2-carbonsäiire    als gelben Nie  derschlag abscheidet, zurück. Durch Kristal  lisation aus Eisessig erhält man den Körper  in braungelben Prismen vom F. 173 bis 174'.

        100     Teile    2" .     5"-Diäthoxy-4'-nitrotriphe-          nylamin-2-carbonsäure,    250 Teile     Nitroben-          zol    und 5 Teile Naturkupfer C werden wäh  rend 4 bis 5     Stunden    unter     Rückfluss    er  hitzt. Das Nitrobenzol wird mit Wasser  dampf abgetrieben. Es bleibt ein in der  gälte erstarrendes, braunes 01 zurück. Durch       Kristallisation    aus Alkohol erhält man das  2' . 5' -     Diäthoxy    - 4 -     nitrotriphenylamin    in  orangegelben Kristallen vom F. 102 bis 103  .

    Durch Reduzieren     mit    Eisen und Salzsäure  in Alkohol erhält man das 2'.     5'-Diäthoxy-          4-aminotriphenylamin    in farblosen Prismen  vom F. 138 bis 139  .



  <B> Additional patent </B> to main patent no. 163540. Process for the production of a new azo dye. It has been found that a new azo dye of the formula
EMI0001.0004
    if you get the 2 '. 5'-diethoxy-4-cli- azotripheiiylamine with the m-chloroanilide of. 3-oxynaphthoic acid couples.



  The dye thus obtained forms a blue powder, produced on suitable substrates such as cotton, wool, rayon, and dyes them in pure, very real blue tones.



  <I> Example: </I> 34.8 '.feile 2'. 5'-Diethoxy-4-aminotriphenylamine are diazotized as usual and poured into a solution of 29.7 parts of the m-chloroanilide of 2,3-oxynaphthoic acid, 60 parts of 30% sodium hydroxide solution, 15 parts of soda and 2000 parts of water registered. The dye formed precipitates immediately. It is filtered, washed and dried.



  The 2 '. 5'-diethoxy - 4 - aminotriphenylamine can be represented as follows: 150 parts 2 '. 5'-diethoxytriphenylamine-2-carboxylic acid, mp 170 to 171, 187.5 parts of p-nitroiodobenzene, .80 parts of potassium carbonate, 375 parts of nitrobenzene and 5 parts of natural copper C are for one hour at <B> 195 </B> warmed up to 200 'in an oil bath.

   The nitrobenzene and the excess p-nitroiodobenzene are driven off with steam. A brown-red solution remains, from which the 2 ". 5" -Diethoxy-4'-nitro-triphenylamine-2-carboxylic acid is deposited as a yellow precipitate with hydrochloric acid. Crystallization from glacial acetic acid gives the body in brown-yellow prisms from F. 173 to 174 '.

        100 parts of 2 ". 5" diethoxy-4'-nitrotriphenylamine-2-carboxylic acid, 250 parts of nitrobenzene and 5 parts of natural copper C are refluxed for 4 to 5 hours. The nitrobenzene is driven off with steam. What remains is a brown 01 that solidifies in the cold. The 2 'is obtained by crystallization from alcohol. 5 '- diethoxy - 4 - nitrotriphenylamine in orange-yellow crystals from F. 102 to 103.

    The 2 'is obtained by reducing with iron and hydrochloric acid in alcohol. 5'-diethoxy-4-aminotriphenylamine in colorless prisms from F. 138 to 139.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azo- farbstoffes der Formel EMI0002.0016 dadurch gekennzeichnet, dass man das 2' . 5'- Diäthoxy - 4 - diazotriphenylamin mit dem m-Chloranilid der 2.3-Oxynaphthoesälire 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 2 '. 5'-diethoxy-4-diazotriphenylamine couples with the m-chloroanilide of the 2,3-oxynaphthoic acid. Produced on suitable substrates such as cotton, wool, rayon, he dyes them in pure, very real blue tones.
CH166077D 1932-07-13 1932-07-13 Process for the production of a new azo dye. CH166077A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH163540T 1932-07-13
CH166077T 1932-07-13

Publications (1)

Publication Number Publication Date
CH166077A true CH166077A (en) 1933-12-15

Family

ID=25717794

Family Applications (1)

Application Number Title Priority Date Filing Date
CH166077D CH166077A (en) 1932-07-13 1932-07-13 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH166077A (en)

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