CH205165A - Process for the preparation of a water-soluble monoazo dye. - Google Patents
Process for the preparation of a water-soluble monoazo dye.Info
- Publication number
- CH205165A CH205165A CH205165DA CH205165A CH 205165 A CH205165 A CH 205165A CH 205165D A CH205165D A CH 205165DA CH 205165 A CH205165 A CH 205165A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- preparation
- dye
- monoazo dye
- soluble monoazo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- MWFMCZWMLLCBJH-UHFFFAOYSA-N o-naphthalen-1-ylhydroxylamine Chemical class C1=CC=C2C(ON)=CC=CC2=C1 MWFMCZWMLLCBJH-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen iVIonoazofarbstoffes. Es wurde gefunden, dass man zu wert vollen wasserlöslichen Monoazofarbs,toffen
EMI0001.0004
worin R einen Naphthalinkern bedeutet, .der noch weiter substituiert sein kann, aber keine Sulfonsäuregruppe enthalten darf, X und Y für Wasserstoff oder Alkyl stehen, und wo bei, soweit Verbindungen,der Gruppierung 1) in Frage kommen,
Abkömmlinge des 1-Amino- 7-oxynaphthalins ausgeschlossen sein sollen, mit beliebigen Diazoverbindungen der Benzol reihe, die keine löslichmachend@en Gruppen enthalten, in saurem oder alkalischem Medium vereinigt. Die erhaltenen Farbstoffe eignen sich ins- besondere zum Färben von Wolle aus saurem Bade unter Kochtemperatur, bei<B>60-90'</B> C.
Die als Kupplungskomponenten vierwen- deten Sulfoalkylamino-.oxynaphthaline kön nen durch, Kondensation der .entsprechenden Amino-oxynaphtbaline mit Halogenalkyl- sulfonsäuren erhalten werden..
Die @Sulfoacyl- amino-oxynaphtbaline sind durch Einwir kung von Chloralkylcarbonsäureehloriden auf die entsprechenden Amino-oxynaphthaline gelangt, wenn man Aminooxynaplhthaline von .der allgemeinen Zusammensetzung und anschliessende Umsetzung, beispielsweise mit Natriumsulfit, erhältlich.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser- löslichen Monoazofarbstoffes, welches da durch gekennzeichnet ist, dass man diazotier- tes Aminobenzol in alkalischem Medium mit 2-Sulfäthyla.mino-7-oxynaphthalin kuppelt. Beispiel:
Zu einer aus 253 Gewichtsteilen 2-Sulf- äthylamino-7-oxynapht.halin,Wasser und 212 Gewichtsteilen Natriumcarbonat erhaltenen Lösung läuft eine in üblicher Weise aus 93 Gewichtsteilen Aminoberizol hergestellte Diazoläs@ung. Nach beendeter Kupplung wird der Farbstoff ausgesalzen, abgesaugt und ge trocknet.
Er stellt ein dunkelbraunes Pulver dar, das sich mit rotbrauner Farbe in Wasser löst und Wolle aus saurem Bade unter Koch- temperatur in rotbraunen Tönen gleichmässig gut durchfärbt.
Process for the production of a water-soluble ionoazo dye. It has been found that valuable water-soluble monoazo dyes can be obtained
EMI0001.0004
where R denotes a naphthalene nucleus, which can be further substituted, but must not contain a sulfonic acid group, X and Y denote hydrogen or alkyl, and where, as far as compounds of grouping 1) are possible,
Derivatives of 1-amino-7-oxynaphthalene should be excluded, combined with any diazo compounds of the benzene series that do not contain any solubilizing groups in an acidic or alkaline medium. The dyes obtained are particularly suitable for dyeing wool from an acid bath under boiling temperature, at <B> 60-90 '</B> C.
The sulfoalkylamino-oxynaphthalenes used as coupling components can be obtained by condensation of the corresponding amino-oxynaphthalenes with haloalkyl-sulfonic acids.
The @ sulfoacylamino-oxynaphthalines are obtained by the action of chloroalkylcarboxylic acid chlorides on the corresponding amino-oxynaphthalenes, if aminooxynaplhthalenes of the general composition and subsequent reaction, for example with sodium sulfite, are available.
The subject of the present patent is a process for the production of a water-soluble monoazo dye, which is characterized in that diazotized aminobenzene is coupled in an alkaline medium with 2-sulfäthyla.mino-7-oxynaphthalene. Example:
To a solution obtained from 253 parts by weight of 2-sulfethylamino-7-oxynapht.halin, water and 212 parts by weight of sodium carbonate, a diazole solution prepared in a conventional manner from 93 parts by weight of aminoberizole runs. After the coupling has ended, the dye is salted out, filtered off with suction and dried.
It is a dark brown powder that dissolves in water with a reddish brown color and dyes wool from an acid bath at boiling temperature in reddish brown shades evenly and thoroughly.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE205165X | 1937-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205165A true CH205165A (en) | 1939-06-15 |
Family
ID=5785739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205165D CH205165A (en) | 1937-03-24 | 1938-03-17 | Process for the preparation of a water-soluble monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205165A (en) |
-
1938
- 1938-03-17 CH CH205165D patent/CH205165A/en unknown
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