CH220430A - Process for the preparation of an asymmetrical azo dye. - Google Patents

Process for the preparation of an asymmetrical azo dye.

Info

Publication number
CH220430A
CH220430A CH220430DA CH220430A CH 220430 A CH220430 A CH 220430A CH 220430D A CH220430D A CH 220430DA CH 220430 A CH220430 A CH 220430A
Authority
CH
Switzerland
Prior art keywords
oxynaphthalene
sulfonic acid
preparation
mole
azo dye
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH220430A publication Critical patent/CH220430A/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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
    • C09B35/16—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy-amines

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 217488.    Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur     Herstellung    eines un  symmetrischen     Azofarbstoffes.    Das Verfah  ren ist dadurch gekennzeichnet, dass man ein       Mol        tetrazotierter        4,4'-Diaminodiphenyl-3,3'-          (bis-oxyessigsäure)    mit einem     Mol        2-Benzoyl-          amino    - 5 -     oxynaphtha.lin    - 7 -     sulfonsäure    und  einem     Mol        2-(2',4'-Dimethoxyphenylamino)

  -          5-oxynaphthalin-7-sulfonsäure    nacheinander  kuppelt.  



  Der neue Farbstoff     ,stellt    ein metallisch       glänzendes    Pulver dar und färbt     Cellulose-          fasern    in marineblauen Tönen. Mit Kupfer  salzen nachbehandelt werden die Färbungen  in ihren Echtheitseigenschaften verbessert.

    <I>Beispiel:</I>  408     Gewichtsteile,diaminodiphenoxyessig-          saures    Kalium werden. in     eiskaltem    Wasser  gelöst und nach Zugabe von 600 Gewichts  teilen     Salzsäure   <B>(,</B>d = 1,18) mit 138     Ge-          wichtsteilen        Natriumnitrit        diazotiert.    Nach         einiger    Zeit wird die     Diazolösung    mit Na:       triumacetat    bis zur essigsauren     Reaktion    ab  gestumpft.

   Bei tiefer Temperatur wird eine  wässerige Lösung von     3,64        Gewichtsteilen          2-benzoylamino-5-oxynaphthalin-7-sulfonsau-          rem    Kalium und 500     Gewichtsteilen        Na-          triumbicarbonat    langsam     eingetropft.    Das       violettblaue    halbseitige     Kupplungsprodukt     wird     nasch    einigen     Stunden        abgesaugt    und  die Paste in eine     eiskalte        sodaalkalisclie        

  Lö-          eung    von 375     Gewichtsteilen    2-(2',4'-Di       methoxyphenylamino)-5-oxynaphthalin-7-sul-          fonsäure    eingetragen. Die gegebenenfalls un  ter Zusatz von     Pyridin        beendete    Kupplung  wird wie üblich     aufgearbeitet.    Man erhält  einen     metallisch    glänzenden     Farbstoff,    der       Cellulosefasern    in marineblauen Tönen an  färbt. Mit Kupfersalzen nachbehandelt wer  den die Färbungen in ihren Echtheitseigen  schaften verbessert.  



  2 -     (2',4'-        Dimethoxyphenylamino)    - 5 -     oxy-          naphthalin-7-sulfonsäure    ist z. B. erhältlich      durch Umsetzen von     1,6-Dioxynaplitlialin-3-          sulfonsäure    mit     1-Amino-2,4-dimetlioxyben-          zol    in     wässeriger    Lösung bei     Gegenwart    von       Natriumbisulfit    oder     auch,    aus     2-Amino-5-          oxynaphtha.lin-7-sulfonsäure    und     1-Amino-          2,

  4-dimethogybenzol    in wässeriger Lösung  durch Kochen mit     Natriumbisulfit    und Am  moniumsulfit.



  <B> Additional patent </B> to the main patent no. 217488. The present invention relates to a process for the production of an asymmetrical azo dye. The process is characterized in that one mole of tetrazotized 4,4'-diaminodiphenyl-3,3'- (bis-oxyacetic acid) is mixed with one mole of 2-benzoylamino - 5 - oxynaphtha.lin - 7 - sulfonic acid and one mole 2- (2 ', 4'-dimethoxyphenylamino)

  - 5-oxynaphthalene-7-sulfonic acid couples one after the other.



  The new dye is a metallic, shiny powder and dyes cellulose fibers in navy blue tones. Treated with copper salts, the dyeings are improved in their fastness properties.

    <I> Example: </I> 408 parts by weight, diaminodiphenoxyacetic acid potassium. dissolved in ice-cold water and, after addition of 600 parts by weight of hydrochloric acid (, d = 1.18), diazotized with 138 parts by weight of sodium nitrite. After some time, the diazo solution is blunted with sodium acetate until it reacts with acetic acid.

   An aqueous solution of 3.64 parts by weight of 2-benzoylamino-5-oxynaphthalene-7-sulphonic acid potassium and 500 parts by weight of sodium bicarbonate is slowly added dropwise at low temperature. The purple-blue half-sided coupling product is sucked off after a few hours and the paste is poured into an ice-cold soda-alkaline solution

  Solution of 375 parts by weight of 2- (2 ', 4'-Di methoxyphenylamino) -5-oxynaphthalene-7-sulphonic acid entered. The coupling, which may have ended with the addition of pyridine, is worked up as usual. A shiny metallic dye is obtained which dyes cellulose fibers in navy blue shades. Aftertreated with copper salts who improves the colorations in their fastness properties.



  2 - (2 ', 4'-dimethoxyphenylamino) - 5 - oxynaphthalene-7-sulfonic acid is z. B. obtainable by reacting 1,6-dioxynaplitlialin-3-sulfonic acid with 1-amino-2,4-dimetlioxyben- zene in aqueous solution in the presence of sodium bisulfite or from 2-amino-5-oxynaphtha.lin-7- sulfonic acid and 1-amino-2,

  4-dimethogybenzene in aqueous solution by boiling with sodium bisulfite and ammonium sulfite.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines unsym metrischen Azofa.rbstoffes, dadurch gekenn zeichnet. -dass man ein Mol tetrazotierter 4,4'-Di"iniinodililienyl-3.3'-(bis-oxy essigsäure) mit einem 31ol 2-Benzoylamino-5-oxynaph- thalin-7-sulfonsäure und einem Mol 2-(2',4'- Dimethoxyplieiiylamino) PATENT CLAIM: Process for the production of an asymmetrical azo-dye, characterized by this. - that one mole of tetrazotized 4,4'-di "iniinodililienyl-3.3 '- (bis-oxy acetic acid) with a 31ol 2-benzoylamino-5-oxynaphthalene-7-sulfonic acid and one mole of 2- (2', 4 '- Dimethoxyplieiiylamino) - 5 -oxynaphthalin-7- sulfonsäure nacheinander kuppelt. Der neue Farbstoff stellt ein metallisch gldinzendes Pulver dar und färbt Cellulose- fasern in marineblauen Tönen. Mit Kupfer salzen nachbehandelt werden die Färbungen in ihren Echtheitseigenschaften verbessert. - 5 -oxynaphthalene-7-sulfonic acid couples one after the other. The new dye is a metallic, shiny powder and colors cellulose fibers in navy blue tones. Treated with copper salts, the dyeings are improved in their fastness properties.
CH220430D 1939-01-25 1940-01-04 Process for the preparation of an asymmetrical azo dye. CH220430A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE220430X 1939-01-25
CH217488T 1940-01-04

Publications (1)

Publication Number Publication Date
CH220430A true CH220430A (en) 1942-03-31

Family

ID=25726034

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220430D CH220430A (en) 1939-01-25 1940-01-04 Process for the preparation of an asymmetrical azo dye.

Country Status (1)

Country Link
CH (1) CH220430A (en)

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