CH302384A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH302384A CH302384A CH302384DA CH302384A CH 302384 A CH302384 A CH 302384A CH 302384D A CH302384D A CH 302384DA CH 302384 A CH302384 A CH 302384A
- Authority
- CH
- Switzerland
- Prior art keywords
- violet
- monoazo dye
- preparation
- parts
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 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 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000725 suspension Substances 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)
- Cosmetics (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstofes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man dianotierten 4-Nitro-2-amino-l-oxyphenyl- (6) - carbaminsäureäthylester in alkalischem Medium mit. 1-Phenylamino-8-oxynaphthalin- 4-slilfon,sa.ire vereinigt.
Der neue Farbstoff löst sieh in Wasser mit Orlaublauer, in verdünnter --\7at.riumearbonat- lösun- mit. brätinliehvioletter, in konzentrier ter Schwefelsäure mit violettroter Farbe und färbt Wolle nach dem Naehchromierverfah- ren in licht- und waschechten, grünen Tönen.
Die Dianotierung des 4-Nitro-2-amino-l- oxyphenyl-(6)-carbaminsäureäthylesters kann nach üblichen Methoden, z. B. mit Hilfe von 1Iineralsäure, insbesondere Salzsäure und Na- tritimnitrit, durchgeführt werden.
Die Kupplung wird in alkalischem, bei spielsweise a.lkalicarbonat- oder alkalihydrox@#d- alkalischem Medium vorgenommen. Beispiel: 24,1.
Teile 4-Nitro 2-amiiio-l-oxyphenyl- (6)-rearbaminsäureäthylester werden in 100 Teilen Wasser aufgeschlämmt und nach Zu- gabe von 20 Teilen 30 % iger Salzsäure und Eis bei 5 bis 10 mit 25 Volumteilen 4n-Na- i
riumnitritlösung in üblicher Weise dianotiert. Die Suspension der Diazoverbindung wird durch Zugabe von Natrittmcarbonat neutrali- siert, mit 25% (bezogen auf das Volumen) Natriumchlorid versetzt und hierauf filtriert.
Die auf diese Weise isolierte Diazoverbindung wird in eine durch Eiszugabe auf 0 abge kühlte Lösung von 33 Teilen 1-Phenylamino- 8-oxynaphtha.lin-4-sulforisäirre in 150 Teilen Wasser, 14 Teilen 30 % iger Natriumhydroxyd- lösung und 12 Teilen wasserfreiem Natrium- carbonat eingetragen.
Man rührt bei langsam ansteigender Temperatur, bis die Kupplung beendet ist, scheidet den Farbstoff durch Zu gabe von Natrilimchlorid vollständig ab und filtriert. Der mit 5%iger Natriumchlorid- lösung gewaschene Filterkuchen wird getrock net.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained when using dianotated 4-nitro-2-amino-1-oxyphenyl- (6) -carbamic acid ethyl ester in an alkaline medium. 1-phenylamino-8-oxynaphthalene-4-silicon, sa.ire united.
The new dye dissolves in water with orange blue, in dilute - \ 7at.rium carbonate solution. Roasting violet, in concentrated sulfuric acid with a violet-red color and dyes wool in light- and washfast green tones using the chromium-plating process.
The dianotation of the 4-nitro-2-amino-l-oxyphenyl- (6) -carbamic acid ethyl ester can be carried out by conventional methods, for B. with the help of 1Iineralsäure, especially hydrochloric acid and sodium tritimnitrite, be carried out.
The coupling is carried out in an alkaline medium, for example a.lkalicarbonat- or alkalihydrox @ # d- alkaline medium. Example: 24.1.
Parts of 4-nitro-2-amino-1-oxyphenyl- (6) -rearbamic acid ethyl ester are suspended in 100 parts of water and, after the addition of 20 parts of 30% strength hydrochloric acid and ice, at 5 to 10 with 25 parts by volume of 4N Na- i
rium nitrite solution dianotiert in the usual way. The suspension of the diazo compound is neutralized by adding sodium carbonate, mixed with 25% (based on the volume) sodium chloride and then filtered.
The diazo compound isolated in this way is poured into a solution, cooled to 0 by the addition of ice, of 33 parts of 1-phenylamino-8-oxynaphtha.lin-4-sulforisäirre in 150 parts of water, 14 parts of 30% sodium hydroxide solution and 12 parts of anhydrous sodium - carbonate registered.
The mixture is stirred at a slowly increasing temperature until the coupling has ended, the dye separates out completely by adding sodium chloride and filtered. The filter cake washed with 5% sodium chloride solution is dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH279910T | 1948-09-03 | ||
| CH302384T | 1949-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302384A true CH302384A (en) | 1954-10-15 |
Family
ID=25731962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302384D CH302384A (en) | 1948-09-03 | 1949-06-29 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302384A (en) |
-
1949
- 1949-06-29 CH CH302384D patent/CH302384A/en unknown
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