CH267274A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH267274A CH267274A CH267274DA CH267274A CH 267274 A CH267274 A CH 267274A CH 267274D A CH267274D A CH 267274DA CH 267274 A CH267274 A CH 267274A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- bordeaux
- purple
- isoamyl
- monoazo dye
- 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 4
- 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
- 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
- 239000000975 dye Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- 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
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000003086 colorant Substances 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
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000009738 saturating Methods 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)
- Paper (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man diazotierte 4-Chlor-2-amino-l-oxybenzol- 6-sulfonsäure mit N-Isoamyl-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 gelbbraunen 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-Isoamyl-4-oxy-2-chino- lon kann z. B. hergestellt. werden, indem man o-Chlorbenzoesättre mit Isoamylamin
EMI0001.0020
kondensiert, die erhaltene 2-Isoamylamino-l- benzoesäure acetyliert und in der 2-Isoamyl- acetyl-amino-l-benzoesäure unter Wasserab spaltung den Ringschluss vollzieht.
Die Ver- einigning des so erhältlichen N-Isoamyl-4-oxy- 2-chinolons mit der diazotierten 4-Chlor-2- amino-l-oxybenzol-6-sulfonsäure kann in üb licher, an sich bekannter Weise, z. B. in alka lischem Medium, erfolgen.
<I>Beispiel:</I> 22,4 Teile 4-Chlor-2-amino-l-oxybenzol-6- sulfonsäure werden in 200 Teilen Wasser mit Hilfe von Salzsäure und Natriumnitrit diazo- tiert. Die Diazolösung wird mit Nat.rium- carbonat neutralisiert und zu einer auf 2 gekühlten Lösung von 23,1 Teilen N-Isoamyl- 4-oxy-2-chinolon in 400 Teilen Wasser, 4 Tei len Natriumhydroxyd und 25 Teilen Natrium- carbonat hinzugegeben.
Man rührt bei 2 bis 5 , bis keine Diazoverbindung mehr naehweis- bar ist. Der entstandene Farbstoff wird hier auf durch Hinzufügen von Natriumchlorid vollständig abgeschieden, abfiltriert und ge trocknet.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained when diazotized 4-chloro-2-amino-1-oxybenzene-6-sulfonic acid is combined with N-isoamyl-4-oxy-2-quinolone.
When dry, the new dye is a purple-black substance that dissolves in dilute sodium carbonate solution with purple color, in concentrated sulfuric acid with red color and colors wool from acetic acid bath in yellow-brown shades, which after chroming turns it into a very good Bordeaux Authenticity properties go beyond. The dye is particularly suitable for dyeing wool using the single-bath chroming process, which also gives very real Bordeaux tones.
The N-isoamyl-4-oxy-2-quino- ion used as starting material in the present process can, for. B. manufactured. by saturating o-chlorobenzoes with isoamylamine
EMI0001.0020
condensed, the 2-isoamylamino-1-benzoic acid obtained acetylated and completes the ring closure in the 2-isoamyl-acetyl-amino-1-benzoic acid with elimination of water.
The union of the N-isoamyl-4-oxy-2-quinolone thus obtainable with the diazotized 4-chloro-2-amino-1-oxybenzene-6-sulfonic acid can be carried out in a conventional manner known per se, e.g. B. in alkaline medium.
<I> Example: </I> 22.4 parts of 4-chloro-2-amino-1-oxybenzene-6-sulfonic acid are diazotized in 200 parts of water with the aid of hydrochloric acid and sodium nitrite. The diazo solution is neutralized with sodium carbonate and added to a solution, cooled to 2, of 23.1 parts of N-isoamyl-4-oxy-2-quinolone in 400 parts of water, 4 parts of sodium hydroxide and 25 parts of sodium carbonate.
The mixture is stirred at 2 to 5 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 |
|---|---|---|---|
| CH267274T | 1947-03-14 | ||
| CH261368T | 1947-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267274A true CH267274A (en) | 1950-03-15 |
Family
ID=25730462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267274D CH267274A (en) | 1947-03-14 | 1947-03-14 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267274A (en) |
-
1947
- 1947-03-14 CH CH267274D patent/CH267274A/en unknown
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