CH251583A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH251583A
CH251583A CH251583DA CH251583A CH 251583 A CH251583 A CH 251583A CH 251583D A CH251583D A CH 251583DA CH 251583 A CH251583 A CH 251583A
Authority
CH
Switzerland
Prior art keywords
amino
parts
dye
acid
azo dye
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH251583A publication Critical patent/CH251583A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/16Trisazo dyes
    • C09B31/26Trisazo dyes from other coupling components "D"
    • C09B31/28Heterocyclic compounds

Landscapes

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 245989.    Verfahren zur -Herstellung     eines        Azofarbstoffes.       Es wurde gefunden, dass ein wertvoller       Azofarbstoff    hergestellt werden kann, wenn  man     diazotierte        4-Amino-4'-oxy-1,1'-azoben-          zol-3,3'-dicarbonsäure    in alkalischem     Medium     mit     2-Amino-5-oxynaphthalin-7-sul'fonsäure     kuppelt,

   den     erhaltenen        Aminodisazofarb-          stoff        weiterdiazotiert        und    mit     8-Oxychinolin     kuppelt.  



  Der neue Farbstoff stellt in trockenem  Zustand ein     schwarzes    Pulver dar, das sich  in Wasser mit violetter, in     verdünnter    Na  tronlauge mit     rotstichig    blauer, in     konz.     Schwefelsäure mit blauer Farbe löst und       Baumwolle    nach dem ein- oder     zweibadigen          Nachkupferungsverfahren    in marineblauen  Tönen färbt.  



  Die     Diazotierung    der 4 -     Amino    -     4'-oxy-          1,1'-azobenzol-3,3'-dicarbonsäure    kann vor  teilhaft auf     indirektem    Wege vorgenommen       ,verden,    indem zum Beispiel eine neutrale  oder alkalische Lösung des Ausgangsstoffes  mit     Nitrit    versetzt und in gekühlte Säure  lösung eingegossen wird. Die Kupplung mit       2-Amino-5-oxynaphthalin-7-sulfonsäure    wird  in alkalischem, beispielsweise     natriumcarbo-          natalkalischem    Medium durchgeführt.

   Die       Diazotierung    des     Aminodisazofarbstoffes    er  folgt ebenfalls mit     Vorteil    nach dem     bereits     erwähnten,     indirekten    Verfahren, und die  Kupplung mit     8-Oxy        chinolin    vorzugsweise  in alkalischem, z. B.     natriumcarbonatalkali-          schem,    Medium.

           Beispiel:     Man löst 30,1 Teile 4 -     Amino    - 4' -o     xy-          1,1'-azobenzol-3,ä'-dicarbonsäure    mit 27 Tei  len 30     %iger    Natronlauge in 200 Teilen Was  ser und gibt 7 Teile     Natriumnitrit    zu. Die  klare     Lösung    giesst man     m    eine Mischung  von Eis, 100 Teilen 20%iger Schwefelsäure  und 30 Teilen     Naphthalinsulfonsäure,        wobei     die Temperatur 10 bis 15  betragen soll.

   Man  rührt eine     Stunde    und giesst den     Diazobrei    in       eine    gekühlte Lösung von 24     Teilen        2-Amino-          5-oxynaphthalin-7-s@ulfonsäure    und 40     Teilen          Natriumcarbonat.    Nach erfolgter     Kupplung     fällt man den     Aminodisazofarbstöff    durch  Zufügen von Kochsalz. Man filtriert ihn, löst  in 300 Teilen     Wasser,    gibt 7 Teile Natrium  nitrit zu und giesst in eine Mischung von 62  Teilen 30%iger Salzsäure und 200 Teilen  Eis.

   Man rührt 2 Stunden bei 5 bis 10  und  giesst den     Diazobrei        in    eine     gekühlte    Suspen  sion von 15 Teilen     8-Oxychinolin    in 300 Tei  len     20%iger        Natriumcarbonatlö.sung.    Nach  erfolgter Kupplung wird der Farbstoff fil  triert und getrocknet.



  <B> Additional patent </B> to main patent no. 245989. Process for the production of an azo dye. It has been found that a valuable azo dye can be produced if diazotized 4-amino-4'-oxy-1,1'-azoben-zene-3,3'-dicarboxylic acid in an alkaline medium with 2-amino-5-oxynaphthalene -7-sulphonic acid couples,

   the aminodisazo dye obtained is further diazotized and coupled with 8-oxyquinoline.



  When dry, the new dye is a black powder that dissolves in water with violet, in dilute sodium hydroxide solution with reddish blue, in conc. Sulfuric acid with a blue color dissolves and dyes cotton in navy blue shades using the one or two-bath copper plating process.



  The diazotization of the 4 - amino - 4'-oxy-1,1'-azobenzene-3,3'-dicarboxylic acid can be made before geous in an indirect way, verden by, for example, a neutral or alkaline solution of the starting material with nitrite and in cooled acid solution is poured. The coupling with 2-amino-5-oxynaphthalene-7-sulfonic acid is carried out in an alkaline, for example sodium carbonate-alkaline, medium.

   The diazotization of the aminodisazo dye it also follows with advantage by the indirect method already mentioned, and the coupling with 8-oxy quinoline preferably in alkaline, z. B. sodium carbonate alkaline medium.

           Example: Dissolve 30.1 parts of 4-amino-4'-oxy-1,1'-azobenzene-3, ä'-dicarboxylic acid with 27 parts of 30% sodium hydroxide solution in 200 parts of water and 7 parts of sodium nitrite are added . The clear solution is poured into a mixture of ice, 100 parts of 20% strength sulfuric acid and 30 parts of naphthalenesulfonic acid, the temperature being 10-15.

   The mixture is stirred for one hour and the diazo slurry is poured into a cooled solution of 24 parts of 2-amino-5-oxynaphthalene-7-sulfonic acid and 40 parts of sodium carbonate. After coupling has taken place, the aminodisazo dye is precipitated by adding sodium chloride. It is filtered, dissolved in 300 parts of water, 7 parts of sodium nitrite are added and the mixture is poured into a mixture of 62 parts of 30% strength hydrochloric acid and 200 parts of ice.

   The mixture is stirred for 2 hours at 5 to 10 and the diazo paste is poured into a cooled suspension of 15 parts of 8-oxyquinoline in 300 parts of 20% strength sodium carbonate solution. After coupling has taken place, the dye is filtered off and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azo- farbstoffes, dadurch gekennzeichnet, dass man diazotierte 4-Amino-4'-oxy-1,1'-azoben- zol-3,3'-dicarbonsäure in alkalischem Medium mit 2-Amino-5-oxynaphthalin - 7 - sulfonsäure kuppelt, den erhaltenen Aminodisazofarb- stoff weiterdiiazotiert und mit 8-Ogychinolin kuppelt. PATENT CLAIM: Process for the production of an azo dye, characterized in that diazotized 4-amino-4'-oxy-1,1'-azobenzene-3,3'-dicarboxylic acid in an alkaline medium with 2-amino-5- oxynaphthalene-7-sulfonic acid couples, the aminodisazo dye obtained is further diiazotized and couples with 8-ogyquinoline. Der neue Farbstoff stellt in trockenem Zustand ein schwarzes Pulver dar, das sich in Wasser mit violetter, in verdünnter Na- tronlauge mit rotstichig blauer, in konz. Schwefelsäure mit blauer Farbe löst und Baumwolle nach dem ein- oder zweibadigen Nachkupferungsverfahren in marineblauen Tönen färbt. When dry, the new dye is a black powder that dissolves in water with violet, in dilute sodium hydroxide with reddish blue, in conc. Sulfuric acid with a blue color dissolves and dyes cotton in navy blue shades using the one or two-bath copper plating process.
CH251583D 1944-12-19 1944-12-19 Process for the preparation of an azo dye. CH251583A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH251583T 1944-12-19
CH616977X 1944-12-19

Publications (1)

Publication Number Publication Date
CH251583A true CH251583A (en) 1947-10-31

Family

ID=25729547

Family Applications (1)

Application Number Title Priority Date Filing Date
CH251583D CH251583A (en) 1944-12-19 1944-12-19 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH251583A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE917990C (en) * 1951-07-05 1954-09-16 Ciba Geigy Process for the preparation of new trisazo dyes
DE944881C (en) * 1953-02-27 1956-06-28 Bayer Ag Process for the preparation of metal complex-forming azo dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE917990C (en) * 1951-07-05 1954-09-16 Ciba Geigy Process for the preparation of new trisazo dyes
DE944881C (en) * 1953-02-27 1956-06-28 Bayer Ag Process for the preparation of metal complex-forming azo dyes

Similar Documents

Publication Publication Date Title
CH286500A (en) Process for the preparation of a monoazo dye.
CH238454A (en) Process for the preparation of a copper-compatible polyazo dye.
CH251583A (en) Process for the preparation of an azo dye.
CH283989A (en) Process for the preparation of a monoazo dye.
CH268397A (en) Process for the preparation of an azo dye.
CH279910A (en) Process for the preparation of a monoazo dye.
CH308401A (en) Process for the preparation of a monoazo dye.
CH282263A (en) Process for the preparation of a monoazo dye.
CH282261A (en) Process for the preparation of a monoazo dye.
CH240364A (en) Process for the preparation of a disazo dye.
CH261836A (en) Process for the preparation of a monoazo dye.
CH260306A (en) Process for the preparation of a disazo dye.
CH282256A (en) Process for the preparation of a monoazo dye.
CH200370A (en) Process for the preparation of a chromable o-oxydisazo dye.
CH282258A (en) Process for the preparation of a monoazo dye.
CH308402A (en) Process for the preparation of a monoazo dye.
CH263536A (en) Process for the preparation of a disazo dye.
CH239324A (en) Process for the preparation of a disazo dye.
CH308761A (en) Process for the preparation of a monoazo dye.
CH296533A (en) Process for the preparation of a monoazo dye.
CH237725A (en) Process for the preparation of a new monoazo dye.
CH203864A (en) Process for the preparation of a disazo dye.
CH309428A (en) Process for the preparation of a copperable disazo dye.
CH251584A (en) Process for the preparation of an azo dye.
CH299709A (en) Process for the preparation of a trisazo dye.