CH166075A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH166075A CH166075A CH166075DA CH166075A CH 166075 A CH166075 A CH 166075A CH 166075D A CH166075D A CH 166075DA CH 166075 A CH166075 A CH 166075A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- production
- azo dye
- methoxy
- new azo
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff der Formel
EMI0001.0003
erhält, \wenn man das 4'-Methoxy-4-diazo- triphenylamin mit dem m - Nitranilid der 2. 3-Oxynaphthoesäure kuppelt..
Der so erhaltene Farbstoff bildet ein blaues Pulver. Auf geeigneten Substraten, wie zum Beispiel Baumwolle, Wolle, Kunst seide, hergestellt, färbt es diese in reinen, :ehr echten blauen Tönen. <I>Beispiel:</I> 39 Teile 4'-Methoxy-4-aminotriphenyl- amin werden wie üblich diazotiert und in eine Lösung von 30,8 Teilen des m-Nitra- nilids der 2. 3-Oxynaphthoesäure, 60 Teilen 30%iger Natriumhydroxydlösung, 15 Teilen Soda und 2000 Teilen Wasser eingetragen. Der gebildete Farbstoff fällt sofort aus. Er wird filtriert, gewaschen und getrocknet.
Das 4'-Methoxy - 4 - aminotriphenylamin kann wie folgt dargestellt werden: 121,5 Teile 4'-Methoxydiphenylamin-2- ca.rbonsäure, F. 184 bis 18-5 , 187,5 Teile p-Nitrojodbenzol, 80 Teile Kaliumkarbonat (wasserfrei), 375 Teile Nitrobenzol und 5 Teile Naturkupfer C werden während einer Stunde bei 195 bis<B>9-00'</B> im Ölbad erwärmt. Das Nitrobenzol und das überschüssige p-Ni- trojodbenzol werden mit Wasserdampf ab getrieben.
Es bleibt eine braunrote Lösung, aus der man mit Salzsäure die 4"-Methoxy- 4'-nitrodiphenylamino-2-carbonsäure als gel ben Niederschlag abscheidet, zurück. Durch Kristallisieren aus Eisessig erhält man den Körper in orangegelben Blättchen, F. 162 bis 163 . 100 Teile 4"-Methoxy-4'-nitrotriphenyl- amin-2-carbonsäure, 250 Teile Nitrobenzol, 5 Teile Naturkupfer C werden während 4 bis 5 Stunden unter Rückfluss erhitzt. Das Nitro- benzol wird mit Wasserdampf abgetrieben.
Es bleibt ein in der gälte erstarrendes 0l zurück. Durch Kristallisation aus Eisessig erhält man das 4'-Methoxy-4-nitrotriphenyl- amin in orangegelben Blättchen F. P. 110 bis 111 . Durch Reduktion mit Eisen und Salz säure in Alkohol erhält man das V-Methoxy- 4-aminotriphenylamin als farblose Nadeln vom F. 107 bis<B>108'.</B>
Process for the production of a new azo dye. It has been found that a new azo dye of the formula
EMI0001.0003
obtained \ if the 4'-methoxy-4-diazo-triphenylamine is coupled with the m -nitranilide of the 2. 3-oxynaphthoic acid ..
The dye thus obtained forms a blue powder. Produced on suitable substrates, such as cotton, wool, artificial silk, it colors them in pure, real blue tones. <I> Example: </I> 39 parts of 4'-methoxy-4-aminotriphenylamine are diazotized as usual and converted into a solution of 30.8 parts of the m-nitrilide of 2, 3-oxynaphthoic acid, 60 parts of 30 % sodium hydroxide solution, 15 parts of soda and 2000 parts of water entered. The dye formed precipitates immediately. It is filtered, washed and dried.
The 4'-methoxy - 4 - aminotriphenylamine can be represented as follows: 121.5 parts of 4'-methoxydiphenylamine-2-carboxylic acid, F. 184 to 18-5, 187.5 parts of p-nitroiodobenzene, 80 parts of potassium carbonate ( anhydrous), 375 parts of nitrobenzene and 5 parts of natural copper C are heated in an oil bath at 195 to 9-00 'for one hour. The nitrobenzene and the excess p-nitroiodobenzene are driven off with steam.
A brown-red solution remains, from which the 4 "-methoxy-4'-nitrodiphenylamino-2-carboxylic acid is separated out as a yellow precipitate with hydrochloric acid. Crystallization from glacial acetic acid gives the body in orange-yellow leaves, mp 162-163 100 parts of 4 "-methoxy-4'-nitrotriphenylamine-2-carboxylic acid, 250 parts of nitrobenzene, 5 parts of natural copper C are refluxed for 4 to 5 hours. The nitrobenzene is driven off with steam.
There remains an oil that solidifies in the cold. Crystallization from glacial acetic acid gives 4'-methoxy-4-nitrotriphenylamine in orange-yellow leaves F.P. 110 to 111. Reduction with iron and hydrochloric acid in alcohol gives V-methoxy-4-aminotriphenylamine as colorless needles from F. 107 to <B> 108 '. </B>
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH163540T | 1932-07-13 | ||
CH166075T | 1932-07-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH166075A true CH166075A (en) | 1933-12-15 |
Family
ID=25717792
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH166075D CH166075A (en) | 1932-07-13 | 1932-07-13 | Process for the production of a new azo dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH166075A (en) |
-
1932
- 1932-07-13 CH CH166075D patent/CH166075A/en unknown
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