CH176032A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH176032A CH176032A CH176032DA CH176032A CH 176032 A CH176032 A CH 176032A CH 176032D A CH176032D A CH 176032DA CH 176032 A CH176032 A CH 176032A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- dye
- preparation
- monoazo dye
- red
- 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
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 11
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004552 water soluble powder Substances 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstofes. Es wurde gefunden, dass man zu Farb stoffen von wertvollen Eigenschaften ge langt, wenn man Diazoverbindungen vom Aminen der Benzolreihe folgender Konsti tution
EMI0001.0006
(worin X = Wasserstoff oder einen ein wertigen Substituenten ausser Halogen be deutet und. worin der Benzolrest weitere Sub- stituenten enthalten kann)
mit Acylamino-8- naphthol-6-sulfosäuren folgender Konstitu tion
EMI0001.0015
(worin Y = Wasserstoff, Alkyl, Cyeloalkyl oder Aryl bedeutet) kuppelt.
Überraschenderweise weisen die vor liegenden Farbstoffe gegenüber den bekann ten analogen Farbstoffen wesentlich bessere färberische Eigenschaften, insbesondere her vorragende Lichtechtheit und Egalisierungs- vermögen, auf. Sie liefern lebhafte, gelb orange, gelbrote, scharlachrote bis blaurote Farbtöne auf Wolle.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines Mono- azofarbstoffes, dadurch gekennzeichnet, dass man die Diazoverbindung der 1-Amino-ben- zol-2-sulfosäure mit der 1-Acetylamino-8- naphthol-6-sulfosäure kuppelt.
Der neue Farbstoff stellt ein dunkelrotes wasserlösliches Pulver dar und färbt Wolle aus saurem Bade in sehr egalen leuchtend blaustichig roten lichtechten Tönen. <I>Beispiel:</I> 17,3 kg 1-Aminobenzol-2-sulfosäure wer den in der üblichen Weise diazotiert. Die er haltene Diazolösung lässt man unter Eisküh lung in eine mit überschüssigem Natrium- bicarbonat versetzte Lösung von 28,5 kg 1-Acetylamino-8-naphthol-6-sulfosäure ein laufen.
Nach beendeter Kupplung wird der Farbstoffs ausgesalzen, abfiltriert und ge- irocknet.
Process for the preparation of a monoazo dye. It has been found that dyes with valuable properties are obtained if diazo compounds from amines of the benzene series of the following constitution are used
EMI0001.0006
(where X = hydrogen or a monovalent substituent other than halogen and where the benzene radical can contain further substituents)
with acylamino-8-naphthol-6-sulfonic acids of the following constitution
EMI0001.0015
(where Y = hydrogen, alkyl, cyeloalkyl or aryl) couples.
Surprisingly, the dyes present have significantly better coloring properties than the known analogous dyes, in particular excellent light fastness and leveling capacity. They deliver lively, yellow-orange, yellow-red, scarlet to blue-red hues on wool.
The present patent relates to a process for the production of a monoazo dye, characterized in that the diazo compound of 1-amino-benzene-2-sulfonic acid is coupled with 1-acetylamino-8-naphthol-6-sulfonic acid.
The new dye is a dark red, water-soluble powder and dyes wool from an acid bath in very even, bright blue-tinged red, lightfast shades. <I> Example: </I> 17.3 kg of 1-aminobenzene-2-sulfonic acid who diazotized in the usual way. The diazo solution obtained is run under ice cooling into a solution of 28.5 kg of 1-acetylamino-8-naphthol-6-sulfonic acid to which excess sodium bicarbonate has been added.
When the coupling is complete, the dye is salted out, filtered off and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE176032X | 1933-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH176032A true CH176032A (en) | 1935-03-31 |
Family
ID=5696037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176032D CH176032A (en) | 1933-08-22 | 1934-07-27 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH176032A (en) |
-
1934
- 1934-07-27 CH CH176032D patent/CH176032A/en unknown
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