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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
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)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH157035T | 1931-11-30 | ||
CH163182T | 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 |
---|---|---|---|
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. |
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. |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH160674D CH160674A (en) | 1931-11-30 | 1931-11-30 | Process for the preparation of an azo dye. |
Country Status (1)
Country | Link |
---|---|
CH (4) | CH160681A (en) |
Families Citing this family (3)
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 |
EP0577556B1 (en) * | 1992-06-30 | 1997-01-15 | Ciba SC Holding AG | Process for the trichromatic dyeing of leather with dye mixtures |
-
1931
- 1931-11-30 CH CH160681D patent/CH160681A/en unknown
- 1931-11-30 CH CH163182D patent/CH163182A/en unknown
- 1931-11-30 CH CH157035D patent/CH157035A/en unknown
- 1931-11-30 CH CH160674D patent/CH160674A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH160681A (en) | 1933-03-15 |
CH160674A (en) | 1933-03-15 |
CH163182A (en) | 1933-07-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH157035A (en) | Process for the preparation of an azo dye. | |
DE406504C (en) | Process for the preparation of yellow-brown stain-coloring disazo dyes | |
DE2306769A1 (en) | POLYAZO CONNECTION, ITS MANUFACTURING AND USE | |
DE411332C (en) | Process for the preparation of yellow-brown stain-coloring disazo dyes | |
CH198053A (en) | Process for the preparation of a polyazo dye. | |
CH160676A (en) | Process for the preparation of an azo dye. | |
CH215063A (en) | Process for the production of a copper-containing trisazo dye. | |
CH131257A (en) | Process for the production of a new azo dye. | |
CH128916A (en) | Process for the preparation of the copper compound of a substantive azo dye. | |
CH138229A (en) | Process for the production of a new azo dye. | |
CH183456A (en) | Process for the preparation of a new trisazo dye. | |
CH170768A (en) | Process for the preparation of a substantive copper-containing azo dye. | |
CH166069A (en) | Process for the preparation of an azo dye. | |
CH138211A (en) | Process for the production of a new metal-containing dye. | |
CH160679A (en) | Process for the preparation of an azo dye. | |
CH175882A (en) | Process for the preparation of a substantive copper-containing azo dye. | |
CH174652A (en) | Process for the production of a new azo dye. | |
CH138234A (en) | Process for the production of a new azo dye. | |
CH175885A (en) | Process for the preparation of a substantive copper-containing azo dye. | |
CH160675A (en) | Process for the preparation of an azo dye. | |
CH163184A (en) | Process for the preparation of an azo dye. | |
CH183457A (en) | Process for the preparation of a new trisazo dye. | |
CH310150A (en) | Process for the preparation of a copper-containing disazo dye. | |
CH106931A (en) | Process for the preparation of a monoazo dye. | |
CH175881A (en) | Process for the preparation of a substantive copper-containing azo dye. |