CH182961A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH182961A
CH182961A CH182961DA CH182961A CH 182961 A CH182961 A CH 182961A CH 182961D A CH182961D A CH 182961DA CH 182961 A CH182961 A CH 182961A
Authority
CH
Switzerland
Prior art keywords
azo dye
production
new azo
aminobenzene
new
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 CH182961A publication Critical patent/CH182961A/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

  

  Verfahren zur Herstellung eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    erhält, wenn man     diazotiertes     4 - (4'-     Methyl)    -     phenoxyacetylamino-    225     -di-          (ss-äthoxyäthyläther)-1-aminobenzol    mit     2,3-          Oxynaphthoesäureanilid    vereinigt. Der neue  Farbstoff bildet ein blaues, in Wasser unlös  liches Pulver. Auf geeigneten Substraten,  wie zum Beispiel     Zellulose,    hergestellt, färbt  es diese in wertvollen blauen. Tönen.

      <I>Beispiel:</I>    43,2 Teile     4-(4'-Methyl)-phenoxyacetyl-          amino-    2, 5 -     di-(ss-äthoxyäthyläther)-1-amino-          benzol    werden wie üblich     diazotiert    und in  eine Lösung von     216,3    Teilen     2,3-Oxynaph-          thoesäureanilid,    60 Teilen 30 %     iger    Natron  lauge,     3:0    Teilen Soda und 2000 Teilen Was  ser eingetragen. Der     gebildete    Farbstoff fällt  sofort aus. Der blaue Niederschlag wird fil  triert und getrocknet.  



  Das     4-(4'-Methyl)-phenoxyacetylamino-          2,5    -     di-(ss-äthoxyäthyläther)        -1-aminobenzol       kann hergestellt werden durch Umsetzen von       2"5-Dichlor-o-nitrobenzol    mit     Glykolmono-          äthyläther    zum 4 - Chlor- 2 -     nitrobenzol-    1-ss  äthoxyäthyläther.

   Dieser wird dann zum     4-          Chlor-2-aminobenzol-l-ss-äthoxyKthyläther    re  duziert, welcher     acetyliert,    nitriert und hier  auf durch Abspalten der     Acetylgruppe    in den  5 -     Nitro    - 4-     chlor-2    -     aminobenzol    -1     -ss-        äthoxy-          äthyläther    übergeführt wird.

   Dieses Produkt       wird    nun nochmals mit     Glykolmonoäthyl-          äAher    umgesetzt, wobei das     4-ständige    Chlor  atom durch die Gruppe - O -     CH,CH2    -     OC,H5     ersetzt wird und hierauf durch     Kondensation     mit der     4-(Methyl)-phenoxyessigsäure    und  Reduzieren in das     4-(4'-Methyl)-phenoxy-          acetylamino    -<B>2,5</B> -     di    -     (ss    -     äthoxyäthyläther)

          -1-          aminobenzol    umgewandelt wird.



  Process for the production of a new azo dye. It has been found that a new azo dye is obtained if diazotized 4 - (4'-methyl) - phenoxyacetylamino-225-di (ss-ethoxyethyl ether) -1-aminobenzene is combined with 2,3-oxynaphthoic anilide. The new dye forms a blue, water-insoluble powder. Produced on suitable substrates, such as cellulose, it colors them in valuable blue. Tones.

      <I> Example: </I> 43.2 parts of 4- (4'-methyl) -phenoxyacetyl-amino-2, 5-di- (ss-ethoxyethyl ether) -1-aminobenzene are diazotized as usual and in a Solution of 216.3 parts of 2,3-oxynaphthoic anilide, 60 parts of 30% strength sodium hydroxide solution, 3: 0 parts of soda and 2000 parts of water entered. The dye formed precipitates immediately. The blue precipitate is filtered off and dried.



  The 4- (4'-methyl) -phenoxyacetylamino-2,5-di- (ss-ethoxyethyl ether) -1-aminobenzene can be prepared by reacting 2 "5-dichloro-o-nitrobenzene with glycol monoethyl ether to give 4 - chlorine - 2 - nitrobenzene- 1-ss ethoxyethyl ether.

   This is then reduced to 4-chloro-2-aminobenzene-1-ss-äthoxyKthyläther, which acetylated, nitrated and here on by splitting off the acetyl group in the 5 - nitro - 4-chloro-2-aminobenzene -1 -ss- ethoxy - ethyl ether is transferred.

   This product is then reacted again with glycol monoethyl ether, the 4-position chlorine atom being replaced by the group - O - CH, CH2 - OC, H5 and then by condensation with 4- (methyl) phenoxyacetic acid and reduction into the 4- (4'-methyl) -phenoxy- acetylamino - <B> 2.5 </B> - di - (ss - ethoxyethyl ether)

          -1- aminobenzene is converted.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man diazotiertes 4-(4'-Methyl)-phenogyace- tylami_n o- 2,5 - di-(ss-äthogyäthyläther)-1-ami- nobenzol mit 2,3-Ogynaphthoesäureanilid ver einigt. Der neue Farbstoff bildet ein blaues, in Wasser unlösliches Pulver. Auf geeigne- ten Substraten, wie zum Beispiel Zellulose, hergestellt, färbt es diese in wertvollen blauen, Tönen. PATENT CLAIM: Process for the preparation of a new azo dye, characterized in that diazotized 4- (4'-methyl) -phenogyacetylami_n o-2,5-di- (ss-ethogyethyl ether) -1-aminobenzene with 2,3 -Ogynaphthoic anilide united. The new dye forms a blue, water-insoluble powder. Produced on suitable substrates such as cellulose, it colors them in valuable blue tones.
CH182961D 1936-02-11 1935-04-02 Process for the production of a new azo dye. CH182961A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH182961T 1936-02-11

Publications (1)

Publication Number Publication Date
CH182961A true CH182961A (en) 1936-03-15

Family

ID=4431931

Family Applications (1)

Application Number Title Priority Date Filing Date
CH182961D CH182961A (en) 1936-02-11 1935-04-02 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH182961A (en)

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