CH218809A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH218809A CH218809A CH218809DA CH218809A CH 218809 A CH218809 A CH 218809A CH 218809D A CH218809D A CH 218809DA CH 218809 A CH218809 A CH 218809A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- dye
- preparation
- leather
- red
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 239000010985 leather Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- QBLCRXSRSFKFFQ-UHFFFAOYSA-N 4-amino-3-chloro-5-nitrobenzenesulfonic acid Chemical compound [N+](=O)([O-])C=1C=C(C=C(C1N)Cl)S(=O)(=O)O QBLCRXSRSFKFFQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- 238000004043 dyeing Methods 0.000 description 2
- 239000000991 leather dye Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- -1 1-amino-2-chloro-6-nitrobenzene-4-sulfonic acid sodium Chemical compound 0.000 description 1
- NEGPZGPAOPCNPD-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzenesulfonic acid Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1S(O)(=O)=O NEGPZGPAOPCNPD-UHFFFAOYSA-N 0.000 description 1
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Gegenstand des Hauptpatentes Nr. 203691 ist ein Verfahren zur Herstellung eines Azo- farbstoffes, der Wolle und Leder in braunen Tönen anfärbt, welches dadurch gekennzeich net ist, dass man 2 -Chlor - 4 - nitro -1- amino- benzol-6-sulfonsäure diazotiert und mit Di- oxyäthyl-m-toluidin kuppelt.
Wie nun weiter gefunden wurde, erhält man einen zum Färben von Leder in ganz besonderer Weise geeigneten Azofarbstoff, wenn man 1- Amino - 2 - chlor-6-nitrobenzol-4- sulfonsäure diazotiert und mit 1-N-Diäthyl- amino-3-methylbenzol kuppelt. Der erhaltene Farbstoff färbt Leder in klaren blaustichig roten Tönen von guten Echtheitseigenschaften. Diese Färbungen zeichnen sich dadurch aus, dass sie bis zu einer bestimmten Tiefe gleich mässig in das Leder eindringen und beim Schnitt eine klar abgegrenzte Linie gegenüber dem nichtgefärbten Teil zeigen.
Ausserdem besitzt der neue Farbstoff den Vorteil, dass er sich mit andern einfärbenden Lederfarb- stoffen kombinieren lässt, das heisst in Mi schung gefärbt weder vor- noch nachläuft. Weiter zeigt er eine bisher bei einfärben den Lederfarbstoffen noch nicht vorhandene Nuance.
Gegenüber dem Azofarbstoff aus 1-Amino- 2-nitrobenzol-4-sulfonsäure und 1-N-Diäthyl- amino - 3 -methylbenzol, dessen Verwendung zum Bedrucken von Zelluloseestergeweben bekannt ist, besitzt der neue Farbstoff ausser den bereits erwähnten Vorzügen noch den Vorteil einer besseren Alkali- und erheblich besseren Eisenechtheit.
Beispiel: 27,5 Teile 1-amino-2-chlor-6-nitrobenzol- 4-sulfonsaures Natrium werden in 150 Vol.- Teilen Wasser gelöst, worauf die klare Lösung auf ein Gemisch von Eis und 50 Vol.- Teilen Salzsäure von 12 B6 gegossen wird. Temperatur 0 .
Man diazotiert hierauf in der üblichen Weise mit 28 Teilen 25 % iger wässrigerNatriumnitritlösung. Die Diazotierung ist nach etwa '/2 Stunde beendet. Unter Rühren giesst man die Diazoverbindung in eine aus 17 Teilen 1-N-Diäthylamino-3-me- thvlbenzol und 30 Vol-Teilen Salzsäure von 120 Be sowie Wasser bereitete Lösung. Zur Beendigung der Kupplung wird mit 100 Vol.- Teilen 2 n-Natriumacetatlösung abgestumpft.
Man rührt einige Stunden nach, saugt die Farbsäure ab, löst bei<B>600</B> in verdünn ter Natriumkarbonatlösung und salzt aus. Der Farbstoff stellt ein rotes Pulver dar, das sich mit roter Farbe in Wasser spielend leicht löst und das Leder in echten blau stichig roten Tönen einfärbt.
Process for the preparation of an azo dye. The main patent no. 203691 relates to a process for the production of an azo dye which dyes wool and leather in brown tones, which is characterized in that 2-chloro-4-nitro-1-aminobenzene-6-sulfonic acid is used diazotized and coupled with dioxyethyl-m-toluidine.
As has now also been found, an azo dye suitable for dyeing leather in a very special way is obtained if 1- amino-2-chloro-6-nitrobenzene-4-sulfonic acid is diazotized and 1-N-diethylamino-3- methylbenzene couples. The dye obtained dyes leather in clear bluish red shades with good fastness properties. These dyes are characterized by the fact that they penetrate the leather evenly up to a certain depth and show a clearly defined line in relation to the non-dyed part when cut.
In addition, the new dye has the advantage that it can be combined with other coloring leather dyes, that is, when dyed in a mixture, it neither runs ahead nor behind. It also shows a nuance that has not yet existed in the dyeing of leather dyes.
Compared to the azo dye made from 1-amino-2-nitrobenzene-4-sulfonic acid and 1-N-diethylamino-3-methylbenzene, the use of which is known for printing cellulose ester fabrics, the new dye has the advantage of one, in addition to the advantages already mentioned better alkali and considerably better iron fastness.
Example: 27.5 parts of 1-amino-2-chloro-6-nitrobenzene-4-sulfonic acid sodium are dissolved in 150 parts by volume of water, whereupon the clear solution is poured into a mixture of ice and 50 parts by volume of hydrochloric acid of 12 B6 is poured. Temperature 0.
It is then diazotized in the usual way with 28 parts of 25% strength aqueous sodium nitrite solution. The diazotization is over after about 1/2 hour. The diazo compound is poured with stirring into a solution prepared from 17 parts of 1-N-diethylamino-3-methylbenzene and 30 parts by volume of hydrochloric acid of 120 Be and water. To terminate the coupling, 100 parts by volume of 2N sodium acetate solution are blunted.
The mixture is stirred for a few hours, the colored acid is filtered off with suction, dissolved in dilute sodium carbonate solution at <B> 600 </B> and salted out. The dye is a red powder that easily dissolves in water with a red color and colors the leather in real blue, pungent red tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH203691T | 1938-08-27 | ||
| DE218809X | 1939-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH218809A true CH218809A (en) | 1941-12-31 |
Family
ID=25723957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH218809D CH218809A (en) | 1938-08-27 | 1940-03-16 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH218809A (en) |
-
1940
- 1940-03-16 CH CH218809D patent/CH218809A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE723845C (en) | Process for the preparation of a water-soluble monoazo dye | |
| CH209089A (en) | Process for the preparation of a water-soluble dye. | |
| DE728886C (en) | Process for the preparation of copper complex compounds of substantive azo dyes | |
| CH189041A (en) | Process for the preparation of a monoazo dye. | |
| CH189049A (en) | Process for the preparation of a monoazo dye. | |
| CH187427A (en) | Process for the preparation of an azo dye. | |
| CH189048A (en) | Process for the preparation of a monoazo dye. | |
| CH213567A (en) | Process for the preparation of an azo dye. | |
| CH204441A (en) | Process for the production of a new azo dye. | |
| CH212794A (en) | Process for the preparation of an azo dye. | |
| CH177821A (en) | Process for the preparation of an o-oxyazo dye. | |
| CH233354A (en) | Process for the preparation of an o, o'-dioxyazo dye. | |
| CH172572A (en) | Process for the production of a new azo dye. | |
| CH182280A (en) | Process for the preparation of a red monoazo dye. | |
| CH172573A (en) | Process for the production of a new azo dye. | |
| CH209105A (en) | Process for the preparation of an azo dye. | |
| CH169700A (en) | Process for the production of a new azo dye. | |
| CH174519A (en) | Process for the production of a new azo dye. | |
| CH194356A (en) | Process for the preparation of a water-insoluble azo dye. | |
| CH164738A (en) | Process for the production of a new azo dye. | |
| CH125117A (en) | Process for the preparation of a pyrazolone azo dye. | |
| CH189045A (en) | Process for the preparation of a monoazo dye. | |
| CH127170A (en) | Process for the preparation of an azo dye. | |
| CH197177A (en) | Process for the preparation of a black disazo dye. | |
| CH229356A (en) | Process for the preparation of a trisazo dye. |