CH157035A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH157035A
CH157035A CH157035DA CH157035A CH 157035 A CH157035 A CH 157035A CH 157035D A CH157035D A CH 157035DA CH 157035 A CH157035 A CH 157035A
Authority
CH
Switzerland
Prior art keywords
dye
preparation
azo dye
diazo
resorcinol
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 CH157035A publication Critical patent/CH157035A/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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/04—Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/18—Trisazo or higher polyazo dyes
    • C09B33/22—Trisazo dyes of the type A->B->K<-C

Description

  

  Verfahren zur Darstellung eines     Azofarbstofffes.       Bekanntlich gehen die     1.3-Diamine    der       Benzolreihe    bei Behandlung mit     sapetriger     Säure sofort in braune Farbstoffe vom Typus  des     Bismarekbraun    über.  



  Wie nun aber gefunden wurde, lässt sich  das     4-Nitro-1.3-diaminobenzol    in eine     112ono-          diazoverbindung    überführen, welche beim  Kuppeln mit einem aus     1-Diazo-8-naphthol-          3.6-disulfosäure    und     Resorcin    erhaltenen  Farbstoff einen neuen     Polyazofarbstoff    ergibt,  mit welchem tierische Faser, insbesondere  Leder, aus saurem Bade in schönen braunen  Tönen angefärbt wird.  



  Das den Gegenstand der vorliegenden  Erfindung bildende Verfahren ist dadurch  gekennzeichnet, dass man 1     1M1        1.3-Diamino-          4-nitrobenzol        monodiazotiert    und die so er  haltene     Diazoverbindung    in alkalischer Lö  sung mit 1     1flol    eines aus     1-Diazo-8-naphthol-          3.6-disulfosäure    'und     Resorcin    erhältlichen       Farbstoffes    kuppelt.

      <I>Beispiel:</I>  31,9 Teile     1.8-Aminonaphthol-3.6-disulfo-          säure    werden in der üblichen Weise dianotiert  und     untergühlung    in eine Lösung von 11 Teilen       Resorcin    einlaufen gelassen, die mit über  schüssiger Natronlauge alkalisch gehalten  ist. Dann werden 15,3 Teile     1.3-1)iamino-4-          nitrobenzol    in 75 Teilen Wasser und 25 Teilen  konzentrierter Salzsäure heiss gelöst. Die Lö  sung wird heiss in 800 Teile eines Gemisches  von Wasser und Eis gegossen, wobei das  Chlorhydrat grösstenteils in fein verteilter  Form ausfällt.

   Durch Zugabe einer Lösung  von 6,9 Teilen     Natriumnitrit    und kurzes  Rühren wird     monodiazotiert.    Die     111onodiazo-          verbindung    gibt man dann zu dem vorgehend  beschriebenen Reaktionsgemisch, das den       112onoazofarbstoff    aus     1.8-Aminonaphthol-3.6-          disulfosäure    und     Resorcin    enthält, unter Hin  zufügung von so viel Soda, dass nach be  endetem Einlaufen der     Diazoverbindung    noch  alkalische Reaktion besteht. Der     Farbstoff         wird in der üblichen Weise aufgearbeitet  und durch Salzzugabe abgeschieden.

   Er bil  det trocken ein dunkelbraunes bis schwarzes  Pulver und färbt Leder in schönen vollen  braunen Tönen an.



  Process for the preparation of an azo dye. It is known that the 1,3-diamines of the benzene series change immediately into brown dyes of the Bismarek brown type on treatment with sapricous acid.



  As has now been found, however, the 4-nitro-1,3-diaminobenzene can be converted into a 112onodiazo compound which, when coupled with a dye obtained from 1-diazo-8-naphthol-3,6-disulfonic acid and resorcinol, gives a new polyazo dye which animal fiber, especially leather, is dyed from acid bath in beautiful brown tones.



  The process forming the subject of the present invention is characterized in that 1 1M1 1,3-diamino-4-nitrobenzene is monodiazotized and the diazo compound thus obtained is in alkaline solution with 1 1flol of 1-diazo-8-naphthol-3,6-disulfonic acid 'and resorcinol available dye couples.

      <I> Example: </I> 31.9 parts of 1,8-aminonaphthol-3,6-disulfonic acid are dianotized in the usual way and allowed to run under cooling into a solution of 11 parts of resorcinol, which is kept alkaline with excess sodium hydroxide solution. 15.3 parts of 1.3-1) iamino-4-nitrobenzene are then dissolved in 75 parts of water and 25 parts of concentrated hydrochloric acid while hot. The hot solution is poured into 800 parts of a mixture of water and ice, the majority of the hydrochloride precipitating in finely divided form.

   Monodiazotization is carried out by adding a solution of 6.9 parts of sodium nitrite and stirring briefly. The 111onodiazo compound is then added to the reaction mixture described above, which contains the 112onoazo dye of 1,8-aminonaphthol-3,6-disulfonic acid and resorcinol, with the addition of so much soda that an alkaline reaction still exists after the diazo compound has run in. The dye is worked up in the usual way and deposited by adding salt.

   When dry, it forms a dark brown to black powder and stains leather in beautiful, full brown tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man 1 lvIol 1.3-Diamino-4-nitrobenzol monodiazo- tiert und die so erhaltene Diazoverbindung in alkalischer Lösung mit 1 11T o1 eines aus 1-Diazo-8-naphthol-3.6-disulfosäure und Resor- cin erhältlichen Farbstoffes kuppelt. PATENT CLAIM: A process for the preparation of an azo dye, characterized in that 1 lvIol of 1,3-diamino-4-nitrobenzene is monodiazo- tated and the diazo compound obtained in this way is mixed with 11,000 of one of 1-diazo-8-naphthol-3.6 in alkaline solution -disulfonic acid and resorcinol available dye couples. Der so erhaltene Farbstoff bildet trocken ein dunkelbraunes bis schwarzes Pulver und färbt Leder in schönen vollen braunen Tö nen an. The dye obtained in this way forms a dark brown to black powder when dry and stains leather in beautiful full brown tones.
CH157035D 1931-11-30 1931-11-30 Process for the preparation of an azo dye. CH157035A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH163182T 1931-11-30
CH157035T 1931-11-30

Publications (1)

Publication Number Publication Date
CH157035A true CH157035A (en) 1932-09-15

Family

ID=25716869

Family Applications (4)

Application Number Title Priority Date Filing Date
CH157035D CH157035A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.
CH160674D CH160674A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.
CH160681D CH160681A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.
CH163182D CH163182A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.

Family Applications After (3)

Application Number Title Priority Date Filing Date
CH160674D CH160674A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.
CH160681D CH160681A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.
CH163182D CH163182A (en) 1931-11-30 1931-11-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (4) CH157035A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4468348A (en) * 1972-09-26 1984-08-28 Sandoz Ltd. Trisazo dyes having a 4-(1-amino-3,6-disulfo-8-hydroxy-7-phenylazonaphthyl-2-azo)phenylazo group linked to a coupling component radical
US4988804A (en) * 1987-11-10 1991-01-29 Ciba-Geigy Corporation Polyazo dyes obtained by successive coupling of H-acid and two further anilinic diazo components on resorcinol or the like
US5486213A (en) * 1992-06-30 1996-01-23 Ciba-Geigy Corporation Process for the dyeing of leather with dye mixtures

Also Published As

Publication number Publication date
CH160681A (en) 1933-03-15
CH160674A (en) 1933-03-15
CH163182A (en) 1933-07-31

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