CH284992A - Process for preparing a copper-containing azo dye of the stilbene series. - Google Patents
Process for preparing a copper-containing azo dye of the stilbene series.Info
- Publication number
- CH284992A CH284992A CH284992DA CH284992A CH 284992 A CH284992 A CH 284992A CH 284992D A CH284992D A CH 284992DA CH 284992 A CH284992 A CH 284992A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- dye
- containing azo
- azo dye
- preparing
- 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Heratellung eines kupferhaltigen Azofarbstoffes der Stilbenreihe. Es wurde gefunden, daB man zu einem wertvollen, kupferhaltigen Azofarbstoff der Stilbenreihe gelanr;t, wenn man auf den Parb- Process for preparing a copper-containing azo dye of the stilbene series. It has been found that a valuable, copper-containing azo dye of the stilbene series can be obtained by looking at the dye
end anderseits mit dem Aminomonoazofarbstoff der Formel end on the other hand with the aminomonoazo dye of the formula
kondensiert, kupferabgebende Mittel einwirken lâ8t. Der neue Farbstoff bildet ein dunkles Pulver, das sieh in -#N'asser mit brauner Farbe ltist end Baumwolle in lielitechten, oIivstiehig braunen Tônen fârbt. condenses, copper-releasing agents can act. The new dye forms a dark powder which, when wet, has a brown color and dyes cotton in lovely, olive-brown shades.
Die Kondensation der 4,4'-Dinitrostilben- 2,2'-disulfonsâure mit den Aminoazofarbstof- fen, welche zweekmâMig in Form von Alkali- salzen verwendet werden, wird vorteilliaft in wüf.irigerii Medium end in Gegenwart von Al- kalihydroxyd durchgeführt. Gute Ergebnisse werden beispielsweise erhalten, wenn man die miteinander umzusetzenden Stoffe in ver- dünnter, z. B. 2- bis 8 % iger Alkalihy droxyd- Itisung wülirend lângerer Zeit, z. B. 5 bis 24 Stunden bei erh5hter Temperatur, z. B. in stoff, der erhliltlich ist, indem man 4,4'-Di- nitrostilben-2,2'-disulfonsâure einerseits mit dem Aminodisazofarbstoff der Formel offenein GefliP) bei Siedetemperatur des Reak- t ionsgemisehes end enter RfeklluMliüblun oder bei noeh Hberen Temperaturen end enter Druck aufeinander einwirken lâf3t. The condensation of 4,4'-dinitrostilbene-2,2'-disulfonic acid with the aminoazo dyes, which are suitably used in the form of alkali metal salts, is advantageously carried out in a dry medium and in the presence of alkali metal hydroxide. Good results are obtained, for example, if the substances to be reacted with one another are diluted, e.g. B. 2 to 8% alkali hydroxide itization smoldering for a long time, e.g. B. 5 to 24 hours at elevated temperature, e.g. B. in a substance which can be obtained by reacting 4,4'-dinitrostilbene-2,2'-disulphonic acid on the one hand with the aminodisazo dyestuff of the formula open in a vessel at the boiling point of the reaction mixture end enter RfeklluMliüblun or at even higher temperatures end enter pressure interact lâf3t.
Als kupferabgebende Mittel kônnen beim vorliegenden Verfahren z. B. Salze des ein- oder zweiwertigen Kupfers wie Kupfer(I)- ehlorid oder Kupfer(II)-sulfat in Betracht kommen, ferner aueli Verbindungen, die Kup- fer in komplexer Verbindung enthalten. Ins- besondere sind für diesen Zweek Kupfer- amminkomplexe geeignet, wie z. B. die aus Ammoniak, Alkylaminen wie thylamin, Mor- pholin, Pyridin odes Piperidin erhâltlichen Iromplexen Kupferverbindungen. Die Behand- lung mit dem kupferabgebenden Mittel wird zweckmânig in wS,Brigem Medium durchge- führt. Gegebenenfalls kann die Behandlung mit den kupferabgebenden hfitteln in Gegen- wart geeigneter Zusâtze erfolgen. Als solehe seien erw"ahnt ? Basen wie Ammoniak und orga- nische Basen, vorzugsweise ein Z'bersehuB In the present process, e.g. B. Salts of monovalent or divalent copper such as copper (I) - chloride or copper (II) sulfate come into consideration, as well as other compounds containing copper in complex compound. In particular, copper ammine complexes are suitable for this purpose, such as B. the Iromplexen copper compounds obtainable from ammonia, alkylamines such as thylamine, morpholine, pyridine or piperidine. The treatment with the copper-releasing agent is expediently carried out in a wet medium. If necessary, the treatment can be carried out with the copper-releasing substances in the presence of suitable additives. As such, bases such as ammonia and organic bases, preferably an excess, may be mentioned
(hergestellt z. B. aus diazotierter 2-Amino-l.- oxybenzol-4-chlor-6-sulfonsâure, alkalisch ge- kuppelt mit 2-Amino-5-oxynaphthalin-7-sul- fonsâure, weiter diazotiert und sauer gekup- (prepared e.
(hergestellt durch Oxydation der Monoazover- bindung, die durch Kuppeln von diazotierter 4-Nitro-4'-aminostilben-2,2'-disulfonsâure mit 2-Naphthylamin-6-sulfonsâure und dureh Re- duktion der so erhaltenen Nitroverbindung zur entsprechenden Aminoverbindung erhalten wird), 47,4 Teilen des Natriumsalzes der 4,4' Dinitrostilben-2,2'-disulfonsâure, 2400 Teilen Wasser und 240 Teilen 30 % iger Natrium- hydroxydl8sung gemischt und unter RüekfluB wâhrend 22 Stunden zum Sieden erhitzt. Durch Zugabe von Natriumchlorid und Neu- tralisieren eines Teils des Alkaliüberschusses mit Salzsâure kann das gebildete Konden- sationsprodukt aus dem Reaktionsgemisch ab- geschieden werden. Zur i@berführung in die komplexe Kupferverbindung wird das ab- (Prepared by oxidation of the monoazo compound obtained by coupling diazotized 4-nitro-4'-aminostilbene-2,2'-disulfonic acid with 2-naphthylamine-6-sulfonic acid and reducing the nitro compound thus obtained to the corresponding amino compound 47.4 parts of the sodium salt of 4,4'-dinitrostilbene-2,2'-disulphonic acid, 2400 parts of water and 240 parts of 30% sodium hydroxide solution and heated to boiling under reflux for 22 hours. The condensation product formed can be separated from the reaction mixture by adding sodium chloride and neutralizing part of the excess alkali with hydrochloric acid. For the conversion into the complex copper compound, the
derjenigen Base, die bereits im Molekül des gegebenenfalls verwendeten Kupferammin- komplexes enthalten ist. that base which is already contained in the molecule of the copper ammine complex which may be used.
Beispiel: 65 Teile des Natriumsalzes des Disazofarb- stoffes der Formel: pelt mit, l.-Amino-2,5-dimethy lbenzol) werden 60 mit 66,8 Teilen des Trinatriumsalzes des Aminotriazols der Formel filtrierte Kondensationsprodukt in 2400 Tei- len Wasser aufgesehlâmmt. Es werden 40 Teile 25 % ige Ammoniaklbsung zugegeben. Das ge- 16ste Gemisch wird mit 240 Teilen einer 2n- Kupfersulfatl5sung und 240 Teilen 25 % iger Ammoniaklësung wâhrend einer halben Stunde auf 75 erwârmt. Die komplexe Kupferver- bindung lâBt sich durch Aussalzen abscheiden und abfiltrier en. Example: 65 parts of the sodium salt of the disazo dyestuff of the formula: 60 parts of the condensation product filtered with 66.8 parts of the trisodium salt of the aminotriazole of the formula: . 40 parts of 25% strength ammonia solution are added. The stirred mixture is heated to 75 for half an hour with 240 parts of a 2N copper sulphate solution and 240 parts of 25% ammonia solution. The complex copper compound can be separated and filtered off by salting out.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH280185T | 1949-07-29 | ||
CH284992T | 1950-02-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH284992A true CH284992A (en) | 1952-08-15 |
Family
ID=25731976
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH284992D CH284992A (en) | 1949-07-29 | 1950-02-22 | Process for preparing a copper-containing azo dye of the stilbene series. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH284992A (en) |
-
1950
- 1950-02-22 CH CH284992D patent/CH284992A/en unknown
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