CH267275A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH267275A CH267275A CH267275DA CH267275A CH 267275 A CH267275 A CH 267275A CH 267275D A CH267275D A CH 267275DA CH 267275 A CH267275 A CH 267275A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- bordeaux
- benzyl
- purple
- quinolone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 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 3
- 239000000975 dye Substances 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 monoazo carbate Chemical compound 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbatoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man dianotierte 4-Chlor-2-amino-l-oxybenzol- 5-sulfonsäure mit N-Benzyl-4-oxy-2-chinolon vereinigt.
Der neue Farbstoff stellt in trockenem Zustand eine violettschwarze Substanz dar, die sich in verdünnter Natriumcarbonat- lösung mit violetter, in konzentrierter Schwe felsäure mit roter Farbe löst und Wolle aus essigsaurem Bade in braunen Tönen färbt, die durch Nachchromieren in ein Bordeaux von sehr guten Echtheitseigenschaften über gehen. Der Farbstoff eignet sich vorzüglich zum Färben von Wolle nach dem Einbad- chromierverfahren, wobei ebenfalls sehr echte Bordeauxtöne erhalten werden.
Das beim vorliegenden Verfahren als Aus gangsstoff dienende N-Benzyl-4-oxy-2-chinolon kann z. B. hergestellt werden, indem man o- Aminobenzoesäure mit. Benzylchlorid konden siert, die erhaltene 2-Benzylamino-l-benzoe- säure acetyliert und in der 2-Benzyl-acetyl- amino-l-benzoesäure unter Wasserabspaltung den ss.ingschluss vollzieht.
Die Vereinigung des so erhältlichen N-Benzyl-4-oxy-2-chinolons mit der dianotierten 4-Chlor-2-amino-l-oxy- benzol-5-sulfonsäure kann in üblicher, an sich bekannter Weise z. B. in alkalischem Medium erfolgen.
Beispiel: 22,4 Teile 4-Chlor-2-amino-l-oxybenzol-5- sulfonsäure werden in 200 Teilen Wasser mit. Hilfe von Salzsäure und Natriumnitrit dia- zotiert. Die Diazolösung wird mit Natrium- carbonat neutralisiert und zu einer auf 10 gekühlten Lösung von 25,1 Teilen N-Benzyl-4- oxy-2-chinolon in 400 Teilen Wasser,
4 Teilen N atriumhy droxyd und 25 Teilen Natrium- earbonat hinzugegeben. Man rührt bei etwa 15 bis keine Diazoverbindung mehr nachweis bar ist. Der entstandene Farbstoff wird hier auf durch Hinzufügen von Natriumchlorid vollständig abgeschieden, abfiltriert und ge trocknet.
Process for the production of a monoazo carbate. It has been found that a valuable monoazo dye is obtained by combining dianotated 4-chloro-2-amino-1-oxybenzene-5-sulfonic acid with N-benzyl-4-oxy-2-quinolone.
When dry, the new dye is a violet-black substance that dissolves in dilute sodium carbonate solution with violet, in concentrated sulfuric acid with red color and dyes wool from acetic acid bath in brown shades, which are chromed to a Bordeaux with very good fastness properties go over. The dye is particularly suitable for dyeing wool using the single-bath chroming process, which also gives very real Bordeaux tones.
The present process as starting material from N-benzyl-4-oxy-2-quinolone can, for. B. be prepared by o-aminobenzoic acid with. Benzyl chloride condenses, the 2-benzylamino-1-benzoic acid obtained is acetylated and the ss.inclusion is completed in the 2-benzyl-acetylamino-1-benzoic acid with elimination of water.
The combination of the N-benzyl-4-oxy-2-quinolone thus obtainable with the dianotated 4-chloro-2-amino-1-oxybenzene-5-sulfonic acid can be carried out in a conventional manner known per se, for. B. in an alkaline medium.
Example: 22.4 parts of 4-chloro-2-amino-1-oxybenzene-5-sulfonic acid are mixed with 200 parts of water. Diazotized with the help of hydrochloric acid and sodium nitrite. The diazo solution is neutralized with sodium carbonate and added to a solution, cooled to 10, of 25.1 parts of N-benzyl-4-oxy-2-quinolone in 400 parts of water,
4 parts of sodium hydroxide and 25 parts of sodium carbonate were added. The mixture is stirred at about 15 until no more diazo compounds can be detected. The resulting dye is completely deposited by adding sodium chloride, filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261368T | 1947-03-14 | ||
| CH267275T | 1947-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267275A true CH267275A (en) | 1950-03-15 |
Family
ID=25730463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267275D CH267275A (en) | 1947-03-14 | 1947-03-14 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267275A (en) |
-
1947
- 1947-03-14 CH CH267275D patent/CH267275A/en unknown
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