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CH226608A - Process for the production of a copper-containing trisazo dye. - Google Patents

Process for the production of a copper-containing trisazo dye.

Info

Publication number
CH226608A
CH226608A CH226608DA CH226608A CH 226608 A CH226608 A CH 226608A CH 226608D A CH226608D A CH 226608DA CH 226608 A CH226608 A CH 226608A
Authority
CH
Switzerland
Prior art keywords
dye
copper
sulfonic acid
coupled
parts
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH226608A publication Critical patent/CH226608A/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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/36—Trisazo dyes of the type
    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/16—Trisazo dyes
    • C09B31/22—Trisazo dyes from a coupling component "D" containing directive hydroxyl and amino groups
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/362—D is benzene
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/366—D is diphenyl
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/37—D is diarylamine
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/372—D is diarylurea
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/374—D contains two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Chemical Treatment Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electroplating And Plating Baths Therefor (AREA)
  • Treatment Of Fiber Materials (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Electromechanical Clocks (AREA)

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent     Nr.213429.       Verfahren zur     Herstellung    eines kupferhaltigen     Trisazofarbstoifes.       Gegenstand des vorliegenden Zusatz  patentes ist ein Verfahren zur     Darstellung     eines     kupferhaltigen        Trisazofarbstoffes,    da  durch gekennzeichnet,     dass        4'-Oxy-3'-carboxy-          4    -     aminoazobenzol    - 3 -     sulfonsäure        diazotiert,     mit     1-Amino-2-methoxynaphthalin-6-sulfon-          säure    gekuppelt,

   der     Disazofarbstoff        weiter          diazotiert,    die     Diazo-disazoverbindung    mit       2-Benzoylamino    - 6 -     oxynaphthalin-8-sulfon-          säure    gekuppelt und der     gebildete    Farbstoff  durch Umsetzung mit kupferabgebenden  Verbindungen in die     Kupferkomplexverbin,     düng     übergeführt    wird.

      <I>Beispiel:</I>  33,7 Teile     4'-Oxy-3'-carboxy-4-aminoazo-          benzol-3-sulfonsäure,    dargestellt zum Bei  spiel aus     4-Acetyla.mino-l-aminobenzol-3-          sulfonsäure    durch     Diazotierung,    Kupplung  mit     Salicylsäure    und     Verseifung    des     acety-          lierten        Monoazofarbstoffes    mit verdünnter  Natronlauge, werden wie üblich     diazotiert,     mit 25,

  3 Teilen     1-Amino-2-methoxynaph-          thalin-6-sulfonssäure    in Gegenwart von Na-         triumacetat    gekuppelt und der erhaltene  Farbstoff als     Natriumsalz    isoliert. Der       Disazofarbstoff    wird in 1000 Teilen Wasser  gelöst, mit 6,9 Teilen     Natriumnitrit        versetzt     und zu 30 Teilen konzentrierter Salzsäure  und Eis laufen gelassen.

   Nach beendeter       Diazotierung    wird mit einer Lösung von  34,3 Teilen     2-Benzaylamino-6-oxynaphthalin-          8-sulfonsäure    in 200 Teilen     Wasser,    200 Tei  len     Pyridin,    20 Teilen 25 %     igem    Ammoniak  und Eis bei 0  gekuppelt. Der fertig gebil  dete Farbstoff wird mit 5 % Kochsalz     ausge-          salzen,    filtriert und mit 2,5 %     iger    Sole .ge  waschen.  



  Zur     Kupferung    löst man den     Presskuchen     des     Trisazofarbstoffes    in 1500 Teilen Was  ser bei 95 , versetzt mit einer Lösung von  25 Teilen     krist.    Kupfersulfat und hält wäh  rend 5 Stunden bei Siedetemperatur. Der  Farbstoff wird     abfiltriert    und nach bekann  ten Methoden in das     Natriumsulz    überge  führt.  



  Der Farbstoff, ein dunkles Pulver. das  sich in     Wasser    mit blaugrüner Farbe und      in     konz.    Schwefelsäure mit, oliver Farbe löst,  färbt Baumwolle aus dem     Glaubersalzbad    in  grauen Tönen.



  <B> Additional patent </B> to main patent No. 213429. Process for the production of a copper-containing trisazo dye. The subject of the present additional patent is a process for the preparation of a copper-containing trisazo dye, characterized in that 4'-oxy-3'-carboxy-4-aminoazobenzene-3-sulfonic acid diazotizes with 1-amino-2-methoxynaphthalene-6-sulfone - acid coupled,

   the disazo dye is further diazotized, the diazo-disazo compound is coupled with 2-benzoylamino - 6 - oxynaphthalene-8-sulfonic acid and the dye formed is converted into the copper complex compound by reaction with copper-donating compounds.

      <I> Example: </I> 33.7 parts of 4'-oxy-3'-carboxy-4-aminoazobenzene-3-sulfonic acid, prepared for example from 4-Acetyla.mino-l-aminobenzene-3- sulfonic acid by diazotization, coupling with salicylic acid and saponification of the acetylated monoazo dye with dilute sodium hydroxide solution, are diazotized as usual, with 25,

  3 parts of 1-amino-2-methoxynaphthalene-6-sulfonic acid are coupled in the presence of sodium acetate and the dye obtained is isolated as the sodium salt. The disazo dye is dissolved in 1000 parts of water, 6.9 parts of sodium nitrite are added and the mixture is allowed to run into 30 parts of concentrated hydrochloric acid and ice.

   When the diazotization is complete, a solution of 34.3 parts of 2-benzaylamino-6-oxynaphthalene-8-sulfonic acid in 200 parts of water, 200 parts of pyridine, 20 parts of 25% ammonia and ice is coupled at 0. The finished dye is salted out with 5% sodium chloride, filtered and washed with 2.5% brine.



  For coppering, the press cake of the trisazo dye is dissolved in 1500 parts of water at 95, mixed with a solution of 25 parts of crystalline. Copper sulfate and holds during 5 hours at the boiling point. The dye is filtered off and converted into the sodium sulphide by known methods.



  The dye, a dark powder. which is blue-green in water and in conc. Sulfuric acid with an olive color dissolves, dyes cotton from the Glauber's salt bath in gray tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines kupfer haltigen Trisazofarbstoffes, dadurch gekenn zeichnet, da.B 4'-Oxy-3'-carboxy-.l-aminoazo- benzol-3-sulfonsäure diazotiert, mit l-3mino- 2-methoxynaphthalin - 6 - sulfon@säure gekup pelt, der Disazofarbstoff weiter diazotiert, PATENT CLAIM: Process for the preparation of a copper-containing trisazo dye, characterized in that B 4'-oxy-3'-carboxy-.l-aminoazobenzene-3-sulfonic acid diazotized with l-3mino-2-methoxynaphthalene - 6 - sulfonic acid coupled, the disazo dye is further diazotized, die Diazodisazoverbindung mit 2-Benzoyl- amino-6-oxytiapbtlia-lin-8-sulfonsäure gekup- pelt und der bebildete Farbstoff durch Um setzung mit kupferabgebenden Verbindungen in die Iiupferkomplexverbindung überge führt wird. Der Farbstoff, ein dunkles Pulver, the diazodisazo compound is coupled with 2-benzoylamino-6-oxytiapbtlia-lin-8-sulfonic acid and the dye formed is converted into the copper complex compound by reaction with copper-releasing compounds. The dye, a dark powder, das sich in Wasser finit blaugrüner Farbe und in konz. Sehwefelsäure mit oliver Farbe löst färbt Baumvolle aus dein Glaubersalzbad in grauen Tönen. which is finite blue-green in water and in conc. Sulfuric acid with olive color dissolves the tree from your Glauber's salt bath in gray tones.
CH226608D 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye. CH226608A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH213429T 1939-07-20
CH226608T 1940-08-02

Publications (1)

Publication Number Publication Date
CH226608A true CH226608A (en) 1943-04-15

Family

ID=4448239

Family Applications (22)

Application Number Title Priority Date Filing Date
CH215061D CH215061A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215059D CH215059A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215064D CH215064A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215062D CH215062A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215060D CH215060A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215063D CH215063A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215067D CH215067A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215066D CH215066A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215065D CH215065A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH213429D CH213429A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH226609D CH226609A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226616D CH226616A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226610D CH226610A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226612D CH226612A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226615D CH226615A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH224547D CH224547A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226613D CH226613A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226617D CH226617A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226608D CH226608A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226614D CH226614A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226618D CH226618A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226611D CH226611A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.

Family Applications Before (18)

Application Number Title Priority Date Filing Date
CH215061D CH215061A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215059D CH215059A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215064D CH215064A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215062D CH215062A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215060D CH215060A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215063D CH215063A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215067D CH215067A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215066D CH215066A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH215065D CH215065A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH213429D CH213429A (en) 1939-07-20 1939-07-20 Process for the production of a copper-containing trisazo dye.
CH226609D CH226609A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226616D CH226616A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226610D CH226610A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226612D CH226612A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226615D CH226615A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH224547D CH224547A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226613D CH226613A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226617D CH226617A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.

Family Applications After (3)

Application Number Title Priority Date Filing Date
CH226614D CH226614A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226618D CH226618A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.
CH226611D CH226611A (en) 1939-07-20 1940-08-02 Process for the production of a copper-containing trisazo dye.

Country Status (2)

Country Link
CH (22) CH215061A (en)
FR (1) FR866854A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE926506C (en) * 1951-12-13 1955-04-18 Ciba Geigy Process for the production of metal-containing azo dyes of the stilbene series
US3021322A (en) * 1957-11-16 1962-02-13 Cfmc Trisazo cupriferous dyestuffs

Also Published As

Publication number Publication date
CH226611A (en) 1943-04-15
CH226614A (en) 1943-04-15
CH226609A (en) 1943-04-15
CH226612A (en) 1943-04-15
CH226615A (en) 1943-04-15
CH226613A (en) 1943-04-15
CH226618A (en) 1943-04-15
FR866854A (en) 1941-09-15
CH215063A (en) 1941-05-31
CH213429A (en) 1941-02-15
CH226616A (en) 1943-04-15
CH215061A (en) 1941-05-31
CH226610A (en) 1943-04-15
CH215064A (en) 1941-05-31
CH215067A (en) 1941-05-31
CH215062A (en) 1941-05-31
CH215065A (en) 1941-05-31
CH215059A (en) 1941-05-31
CH226617A (en) 1943-04-15
CH215060A (en) 1941-05-31
CH215066A (en) 1941-05-31
CH224547A (en) 1942-11-30

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