CH185838A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH185838A
CH185838A CH185838DA CH185838A CH 185838 A CH185838 A CH 185838A CH 185838D A CH185838D A CH 185838DA CH 185838 A CH185838 A CH 185838A
Authority
CH
Switzerland
Prior art keywords
methyl
production
azo dye
new azo
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 CH185838A publication Critical patent/CH185838A/en

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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. 182961.    Verfahren zur Herstellung eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    erhält, wenn man     diazotiertes    4       (4'-Methyl)-phenoxyacetylamino-2-R-methoxy-          äthyläther-5-methoxy-l-aminobenzol    mit     2,3-          Oxynaphthoesäure-        2'-        methyl    - 4' -     chloranilid     vereinigt. 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.  



  <I>Beispiel</I>  36 Teile 4 - (4'-     Methyl)    -     phenoxyacetyl-          amino    - 2     -,p-        methoxyäthyläther-5-methoxy-l-          aminobenzol    werden wie üblich     diazotiert     und in eine Lösung von 31,1 Teilen     2,3-          Oxynaphthoesäure    -     2'-        methyl    -     4'-        chloranilid,     60 Teilen 30      /oiger    Natronlauge, 30 Teilen  Soda und 2000 Teilen Wasser eingetragen.

    Der gebildete     Farbstoff    fällt sofort aus. Der  blaue Niederschlag wird filtriert und ge  trocknet.    Das     4-(4'-Methyl)-phenoxyacetylamino-2-          ss    -     metlroxyäthyläther    - 5 -     methoxy    - 1-     amino-          benzol    kann hergestellt werden durch Um  setzen von     2,5-Dichlor-o-nitrobenzol    mit Me  thylalkohol zum     4-Chlor-2-nitro-l-metboxy-          benzol.    Dieses wird dann zum     4-Chlor-2-          amino-l-methoxybenzol    reduziert, welches       acetyliert,

      nitriert und durch Abspalten der       Acetylgruppe    in das     5-Nitro-4-chlor--2-amino-          1-methoxybenzol    übergeführt wird. Dieses  Produkt wird nun mit     Glykolmonomethyl-          äther    umgesetzt, wobei das     4-ständige    Chlor  atom durch die Gruppe     0-CH2CH2-OCHs     ersetzt wird, und hierauf durch Kondensation  mit     4-(Methyl)-phenoxyessigsäure    und Redu  zieren in das     4-(4'-Methyl)

  -phenoxyacetyl-          amino-    2 -     ss    -     methoxyäthyl        äther-5-methoxy        -1-          aminobenzol    umgewandelt wird.



  <B> Additional patent </B> to main patent No. 182961. 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-2-R-methoxy-ethyl ether-5-methoxy-1-aminobenzene with 2,3-oxynaphthoic acid-2'-methyl - 4 '- chloranilide combined. 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> 36 parts of 4- (4'-methyl) - phenoxyacetylamino - 2 -, p-methoxyethyl ether-5-methoxy-l-aminobenzene are diazotized as usual and converted into a solution of 31.1 parts 2,3-oxynaphthoic acid-2'-methyl-4'-chloroanilide, 60 parts of 30% sodium hydroxide solution, 30 parts of soda and 2000 parts of water were introduced.

    The dye formed precipitates immediately. The blue precipitate is filtered and dried. The 4- (4'-methyl) -phenoxyacetylamino-2- ss - metlroxyäthyläther - 5 - methoxy - 1- amino-benzene can be prepared by putting 2,5-dichloro-o-nitrobenzene with methyl alcohol to give 4-chloro -2-nitro-l-metboxy-benzene. This is then reduced to 4-chloro-2-amino-1-methoxybenzene, which acetylates

      nitrated and converted into the 5-nitro-4-chloro-2-amino-1-methoxybenzene by splitting off the acetyl group. This product is then reacted with glycol monomethyl ether, the 4-position chlorine atom being replaced by the group 0-CH2CH2-OCHs, and then by condensation with 4- (methyl) -phenoxyacetic acid and reduction to the 4- (4 ' -Methyl)

  -phenoxyacetyl- amino- 2-ss-methoxyethyl ether-5-methoxy -1- aminobenzene is converted.

Claims (1)

.<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man diazotiertes 4-(4'.Methyl)-phenoxyacetyl- amino -2- ss - methoxyäthyl äther - 5 - methoxy-l- aminobenzol mit 2,3-Oxynaphthoesäure-2'- methyl-4'-chloranilid vereinigt. Der neue Farb stoff bildet ein blaues, in Wasser unlösliches Pulver dar. Auf geeigneten Substraten, wie zum Beispiel Zellulose, hergestellt, färbt es diese in wertvollen blauen Tönen. . <B> PATENT CLAIM: </B> Process for the production of a new azo dye, characterized in that diazotized 4- (4'.Methyl) -phenoxyacetyl-amino -2-ss-methoxyethyl ether-5-methoxy-1-aminobenzene combined with 2,3-oxynaphthoic acid-2'-methyl-4'-chloroanilide. The new dye forms a blue, water-insoluble powder. Produced on suitable substrates such as cellulose, it colors them in valuable blue tones.
CH185838D 1936-02-11 1936-02-11 Process for the production of a new azo dye. CH185838A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH182961T 1936-02-11
CH185838T 1936-02-11

Publications (1)

Publication Number Publication Date
CH185838A true CH185838A (en) 1936-08-15

Family

ID=25720813

Family Applications (1)

Application Number Title Priority Date Filing Date
CH185838D CH185838A (en) 1936-02-11 1936-02-11 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH185838A (en)

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