CH278471A - Process for the preparation of an iron-containing disazo dye. - Google Patents

Process for the preparation of an iron-containing disazo dye.

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Publication number
CH278471A
CH278471A CH278471DA CH278471A CH 278471 A CH278471 A CH 278471A CH 278471D A CH278471D A CH 278471DA CH 278471 A CH278471 A CH 278471A
Authority
CH
Switzerland
Prior art keywords
iron
dye
amino
sulfonic acid
disazo dye
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Sandoz
Original Assignee
Ag Sandoz
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 Ag Sandoz filed Critical Ag Sandoz
Publication of CH278471A publication Critical patent/CH278471A/en

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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
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24Disazo or polyazo compounds
    • C09B45/32Disazo or polyazo compounds containing other metals

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

Description

  

      Zusatzpatent    zum Hauptpatent Nr. 274242.    Verfahren zur Herstellung eines eisenhaltigen     Disazofarbatoffes.       Es wurde gefunden, dass man zu wert  vollen     Disazofarbstoffen    und deren Chrom-,  Eisen- und     Kobaltkomplexen    gelangt., indem  man aus, 1     Mol    eines     o-Aminophenols        resp.     eines     o-Ainino-naphthols,

      1     Mol    einer     1-Amino-          8-oxynaphtlialin-sulfonsäitre    und 1     ylol    eines       gegebenenfalls        sulfierten    kupplungsfähigen       Naphtliols,        Disazofarbstoffe    der Formel  
EMI0001.0017     
    aufbaut,

   worin  den     Rest    einer     gegebenenfalls    noch wei  ter substituierten     o-Oxy-diazoverbin-                  dung    der Benzol- oder     Naphtha.linreihe     und  den Rest eines in     o-Stellung    zur     OH-          Gruppe        kuppelnden,    gegebenenfalls  
EMI0001.0028  
       sulfierten        Naphthols    darstellt, wobei     R,

       und     R2    zusammen     mindestens    eine     Sul-          fonsäuregruppe    enthalten sollen, und ein  7, eine     Sulfonsäuregruppe,    das andere Z  Wasserstoff oder eine     Sulfonsäuregruppe    be  deutet, und zwecks Überführung in Chrom  bzw. Eisen oder Kobalt in     komplexer    Form  enthaltende Verbindungen die so gewonnenen       Disazofarbstoffe    bzw.     die    während der Her  stellung     derselben    erhältlichen Monoazofarb-    Stoffe, mit Chrom bzw. Eisen oder Kobalt ab  gebenden     Mitteln    behandelt.  



  Als Ausgangsstoffe können z.     B.    folgende  Verbindungen Verwendung finden:  als     o-Aminophenole        resp.        o-Aminonaphthole          4-Nitro-2-aminophenol,          5-Nitro-2-aminophenol,          4-Chlor-2-aminophenol,          6-Nitro-4-chlor-2-aminophenol,          6-Nitro-2-aminophenol-4-sulfonsättre,     4-N     itro-2-aminaphenol-6-sulfonsäure,          2-Aminophenol-4-sulfonsäure,          4-Chlor-2-aminophenol-6-sulfonsäure,          1-Amino-2-oxy-naphthalin-4-sulfonsäure,

            1-Amino-2-oxy-6-nitronaphthalin-4-su        lfon-          säure,          2-Aminophenol-4,6-disulfonsäure;     als     1-Amino-8-oxynaphthalin-sulfonsäuren:          1-Amino-8-oxynaphthalin-3,6-disulfonsätire,          1-Amino-8-oxynaphthalin-4-sulfonsäure,          1-Amino-8-oxyna,phtha@lin-4,6-disulfonsätire;     als     kupplungsfähiges,        gegebenenfalls        sulfier-          tes        Naphthol:

            ss-Naphthol,          2-Oxynaphth.alin-6-sulfonsäure,          2-Oxyiiaphthalin-4-snlfonsäure,          1-Oxy        naphthalin-4-stilf        onsäiire,          1-Oxy        naphthalin-3-sulfonsäure,          1-Oxynaphthalin-5-sulfonsättre,          1-Oxyna.phthalin-3,6-disiilfonsäure,          1-Oxyn        aphthalin-3,8-distulfonsäure,          1-Oxynaphthalin-4,8-disulfonsäure,          2-Oxynaphl-,halin-3,6-disulfonsätire,          1,

  8-Dioxynaphtlia@lin-3,6-disulfonsäure.         Die neuen Farbstoffe sind sehr gut  wasserlöslich Lind färben Leder in ausgezeich  net lichtechten grauen Tönen.  



  Das vorliegende Patent betrifft ein Ver  fahren zur     Herstellung    eines eisenhaltigen       Disazofarbstoffes,    welches .darin besteht,     da.ss     man     6-Nitro-2-amino-l-oxybcnzol-l-siilfon-          säure        diazotiert,    mit 1-     Amino    - 8 -     oxynaph-          thalin-3,6-disulfonsäiire    kuppelt, den erhal  tenen     Aminoazofarbstoff        weiter.diazotiert,

      mit       2-Oxy        na#phthalin    kuppelt     lind    den nunmehr  vorliegenden     Disazof.arbstoff    mit eisenabge  benden Mitteln behandelt.  



       Beispiel:     23,4 Teile     6-Nitro-2-a.mino-l-oxybenzol-l-          su        lfonsäure    werden auf übliche Weise     diazo-          tiert    und in Gegenwart von überschüssiger Soda.  mit. 31,9 Teilen     1-Amino-8-oxynaphtha.lin-3,6-          disulfonsäiire    gekuppelt. Der     A.minoa.zofarb-          stoff    wird isoliert und hierauf     weiterdiazo-          tiert    und schliesslich mit     2-Oxynaphth.adin    -e-    kuppelt.

   Der so erhaltene     Disazofarbstoff    wird  zur Leberführung in die     Eisenkomplexverbin-          dungen    mehrere Stunden in einer 30 Teile  Eisenvitriol enthaltenden,     wässrigen    Natrium- ;       acetat.lösung    auf 90-100  C erhitzt.  



  Der neue Farbstoff färbt Leder in braun  stichigem grauem Ton von sehr guter Licht  echtheit.



      Additional patent to main patent no. 274242. Process for the production of an iron-containing disazo carbate. It has been found that valuable disazo dyes and their chromium, iron and cobalt complexes can be obtained by converting 1 mol of an o-aminophenol, respectively. of an o-ainino-naphthol,

      1 mol of a 1-amino-8-oxynaphthalenesulfonic acid and 1 ylol of an optionally sulfated, couplable naphthiol, disazo dyes of the formula
EMI0001.0017
    builds up

   in which the remainder of an optionally further substituted o-oxydiazo compound of the benzene or naphtha.lin series and the remainder of a coupling in the o-position to the OH group, optionally
EMI0001.0028
       sulfated naphthol, where R,

       and R2 together should contain at least one sulfonic acid group, and a 7, a sulfonic acid group, the other Z signifies hydrogen or a sulfonic acid group, and for the purpose of conversion to chromium or iron or cobalt in complex form containing compounds the disazo dyes obtained in this way or the during the manufacture of the same available monoazo color substances, treated with chromium or iron or cobalt from donating agents.



  As starting materials, for. B. the following compounds are used: as o-aminophenols, respectively. o-aminonaphthols 4-nitro-2-aminophenol, 5-nitro-2-aminophenol, 4-chloro-2-aminophenol, 6-nitro-4-chloro-2-aminophenol, 6-nitro-2-aminophenol-4-sulfonic saturates , 4-N itro-2-aminaphenol-6-sulfonic acid, 2-aminophenol-4-sulfonic acid, 4-chloro-2-aminophenol-6-sulfonic acid, 1-amino-2-oxy-naphthalene-4-sulfonic acid,

            1-amino-2-oxy-6-nitronaphthalene-4-sulfonic acid, 2-aminophenol-4,6-disulfonic acid; as 1-amino-8-oxynaphthalene-sulfonic acids: 1-amino-8-oxynaphthalene-3,6-disulfonic acid, 1-amino-8-oxynaphthalene-4-sulfonic acid, 1-amino-8-oxyna, phtha @ lin-4 , 6-disulfonic acid; as couplable, possibly sulphated naphthol:

            β-naphthol, 2-oxynaphthalene-6-sulfonic acid, 2-oxynaphthalene-4-sulfonic acid, 1-oxynaphthalene-4-stilfonic acid, 1-oxynaphthalene-3-sulfonic acid, 1-oxynaphthalene-5-sulfonic acid, 1 -Oxyna.phthalin-3,6-disulfonic acid, 1-Oxynaphthalin-3,8-distulfonic acid, 1-Oxynaphthalin-4,8-disulfonic acid, 2-Oxynaphthalin-3,6-disulfonsätire, 1,

  8-Dioxynaphtlia @ lin-3,6-disulfonic acid. The new dyes are very soluble in water and dye leather in excellent lightfast gray tones.



  The present patent relates to a process for the production of an iron-containing disazo dye, which consists in diazotizing 6-nitro-2-amino-1-oxybcnzene-1-sulfonic acid with 1-amino-8-oxynaph- thalin-3,6-disulfonic acid couples, further diazotizes the aminoazo dye obtained,

      Coupled with 2-oxy naphthalene, the disazof dye now available was treated with iron-releasing agents.



       Example: 23.4 parts of 6-nitro-2-a.mino-l-oxybenzene-l-sulfonic acid are diazotized in the usual way and in the presence of excess soda. With. 31.9 parts of 1-amino-8-oxynaphtha.lin-3,6-disulfonic acid coupled. The A.minoa.zo dye is isolated and then further diazotized and finally coupled with 2-oxynaphth.adine-e.

   The disazo dye thus obtained is used to guide the liver into the iron complex compounds for several hours in an aqueous sodium solution containing 30 parts of iron vitriol; acetate solution heated to 90-100 C.



  The new dye dyes leather in a brown, gray shade with very good lightfastness.

 

Claims (1)

PATE NTAN SPRUCH Verfahren zur Herstellung eines eisen haltigen Disazofarbstoffes, dadurch gekenn zeichnet, dass man 6-Nitro-2-amino-l-oxy- benzol-l-su,Ifonsäiire diazotiert, mit 1-Amino- 8 - oxy naplithalin - 3,6 - disulfonsäure kuppelt, den erhaltenen Aminoazofarbstoff weiter- diazotiert, PATE NTAN SPRUCH Process for the production of an iron-containing disazo dye, characterized in that 6-nitro-2-amino-l-oxy-benzene-l-su, ifonsäiire is diazotized with 1-amino-8-oxy naplithalin - 3, 6 - disulfonic acid couples, further diazotizes the aminoazo dye obtained, mit 2-Oxynaphthaliii kuppelt und den nunmehr vorliegenden DisazofarbstofF mit eisenabgebenden Mitteln behandelt. Der neue Farbstoff färbt Leder in braun- stiehi;ein grauem Ton von sehr guter Licht echtheit. coupled with 2-Oxynaphthaliii and treated the disazo dye now present with iron-releasing agents. The new dye dyes leather brown, a gray shade that is very lightfast.
CH278471D 1949-04-14 1950-01-03 Process for the preparation of an iron-containing disazo dye. CH278471A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH274242T 1949-04-14
CH278471T 1950-01-03

Publications (1)

Publication Number Publication Date
CH278471A true CH278471A (en) 1951-10-15

Family

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Family Applications (1)

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CH278471D CH278471A (en) 1949-04-14 1950-01-03 Process for the preparation of an iron-containing disazo dye.

Country Status (1)

Country Link
CH (1) CH278471A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024070669A1 (en) * 2022-09-30 2024-04-04 保土谷化学工業株式会社 Azo pigment, dye composition, colorant and coloring method for positive electrode aluminum oxide, and method for producing azo pigment

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024070669A1 (en) * 2022-09-30 2024-04-04 保土谷化学工業株式会社 Azo pigment, dye composition, colorant and coloring method for positive electrode aluminum oxide, and method for producing azo pigment

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