CH308401A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH308401A CH308401A CH308401DA CH308401A CH 308401 A CH308401 A CH 308401A CH 308401D A CH308401D A CH 308401DA CH 308401 A CH308401 A CH 308401A
- Authority
- CH
- Switzerland
- Prior art keywords
- coupling
- carried out
- monoazo dye
- dye
- alkaline medium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 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 claims description 4
- 239000000975 dye Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man diazotiertes 6-Nitro-4-n-butyrylamino-2- amino-l-oxybenzol mit 2,8-Dioxynaphthalin-6- sulfonsäure vereinigt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sich in heissem Wasser und kalter konz. Schwefelsäure mit etwas rotstichig blauer Farbe löst und Wolle nach dem Nach chromierungsverfahren in blaugrünen Tönen von guten Echtheitseigenschaften färbt.
Die Diazotierung des 6-INTitro-4-n-butyryl- amino-2-amino-l-oxybenzols kann nach an sich bekannten Methoden, z. B. mit Hilfe von Mineralsäure, insbesondere Salzsäure, und Na triumnitrit durchgeführt werden.
Die Kupplung wird zweckmässig in neu tralem bis alkalischem, vorzugsweise in alkali- sehem Medium durchgeführt. Sie kann z. B. in alkaliearbonatalkalischem, alkalihydroxyd- alkalischem oder erdalkalihydroxydalkalischem Medium erfolgen.
<I>Beispiel:</I> 23,9 Teile 6-Nitro-4-n-butyrylamino-2- amino-l-oxybenzol werden in 75 Teilen Was ser und 15 Teilen 30 % iger Chlorwasserstoff säure verrührt und bei 10-15 mit 25 Raum teilen 4n-Natriumnitritlösung in üblicher Weise diazotiert. Nach dem Neutralisieren mit Natriumearbonat wird das Diazotierungsge- misch in eine Lösung aus 26,5 Teilen 2,
8-Di- oxynaphthalin-6-sulfonsäure und 22 Teilen Natriumcarbonat in 150 Teilen Wasser bei 5 bis 10 eingetragen und das Kupplungsge misch so lange gerührt, bis die Farbstoffbil- dung beendet ist. Der gegebenenfalls durch Zusatz von Natriumchlorid vollständig abge schiedene Farbstoff wird abfiltriert, mit wenig 5 Jo iger N atriumchlor idlösung gewaschen und getrocknet.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 6-nitro-4-n-butyrylamino-2-amino-1-oxybenzene is combined with 2,8-dioxynaphthalene-6-sulfonic acid.
The new dye forms a dark powder that is concentrated in hot water and cold. Sulfuric acid dissolves with a somewhat reddish-tinged blue color and dyes wool in blue-green shades with good fastness properties after the chromating process.
The diazotization of 6-INTitro-4-n-butyryl-amino-2-amino-1-oxybenzene can be carried out by methods known per se, e.g. B. with the help of mineral acid, especially hydrochloric acid, and Na trium nitrite.
The coupling is expediently carried out in neutral to alkaline, preferably in alkaline, medium. You can z. B. in alkali carbonate alkaline, alkali hydroxide alkaline or alkaline earth hydroxide medium.
<I> Example: </I> 23.9 parts of 6-nitro-4-n-butyrylamino-2-amino-l-oxybenzene are stirred in 75 parts of water and 15 parts of 30% hydrochloric acid and at 10-15 share with 25 space 4N sodium nitrite solution diazotized in the usual way. After neutralization with sodium carbonate, the diazotization mixture is converted into a solution of 26.5 parts of 2,
8-Dioxynaphthalene-6-sulfonic acid and 22 parts of sodium carbonate in 150 parts of water at 5 to 10 and the coupling mixture stirred until the formation of the dye has ended. The dye, which may have been completely separated out by the addition of sodium chloride, is filtered off, washed with a little 5% sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308401T | 1951-09-14 | ||
| CH303279T | 1952-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308401A true CH308401A (en) | 1955-07-15 |
Family
ID=25734592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308401D CH308401A (en) | 1951-09-14 | 1951-09-14 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308401A (en) |
-
1951
- 1951-09-14 CH CH308401D patent/CH308401A/en unknown
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