CH267277A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH267277A CH267277A CH267277DA CH267277A CH 267277 A CH267277 A CH 267277A CH 267277D A CH267277D A CH 267277DA CH 267277 A CH267277 A CH 267277A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- bordeaux
- purple
- monoazo dye
- oxy
- 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
- 239000000975 dye Substances 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 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
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000005711 Benzoic acid 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
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000006798 ring closing metathesis reaction 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man diazotierte 4-Clilor-2-ainino-l-oxybenzol- 6-sulfonsäure mit N-n-Octyl-4-oxy-2-chinolon vereinigt.
Der neue Farbstoff stellt in trockenem Zustand eine v iolettsehwarze Substanz dar, die sich in verdünnter Natriumearbonatlösung mit violetter, in konzentrierter Schwefelsäure mit rotbrauner Farbe löst und Wolle aus essigsaurem Bade in gelbbraunen Tönen färbt, die durch Naehchromieren in ein Bordeaux von sehr guten Echtheitseigenschaften über gehen. Der Farbstoff eignet sieh vorzüglich zum Färben von Wolle nach dein Einbad- ehromierverfahren, wobei ebenfalls sehr echte Bordeauxtöne erhalten werden.
Das beim vorliegenden Verfahren als Aus gangsstoff dienende N-n-Oct.yl-4-oxy-2-cliino- lon kann z. B. hergestellt werden, indem man o-("lilorbenzoesäiire finit n-Octylamin konden siert,<I>die</I> erhaltene 2-n-Oetylamino-1-benzoe- säure acetyliert und in der 2-n-Oetyl-aeetyl- i amino -1-beii7oesäure unter Wasserabspaltung den Ringschluss vollzieht.
Die Vereinigung des so erhältlichen N-n-Octy l-4-oxy-2-chino- lons mit der diazotierten 4-Clilor-2-amino-l- oxybenzol-6-sulfonsäure kann in üblicher, an sich bekannter Weise z. B. in alkalischem Me- dium erfolgen.
Beispiel: 22,4 Teile 4-Chlor-2-aniino-l-oxybenzol-6- sulfonsäure werden in 200 Teilen Wasser mit Hilfe von Salzsäure und Natriumnitrit diazo- tiert.. Die Diazolösung wird mit Natrium- earbonat neutralisiert und ztt einer auf 5 Uekühlten Lösung von 27,3 Teilen N-n-Octyl- 4-oxy 2-eliinolon in 400 Teilen Wasser,
4 Tei len Natriumhydroxy d und 25 Teilen Natrium- carbonat hinzugegeben. Man rührt bei 10 bis 15 bis keine Diazoverbindung mehr nachweis bar ist. Der entstandene Farbstoff wird durch IIinztifüg@en. von Nat-riumehlorid vollständig abgeschieden, abfiltriert und getrocknet.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 4-chloro-2-ainino-1-oxybenzene-6-sulfonic acid is combined with N-n-octyl-4-oxy-2-quinolone.
When dry, the new dye is a purple-black substance that dissolves in a dilute sodium carbonate solution with a purple color, in concentrated sulfuric acid with a red-brown color and dyes wool from an acetic acid bath in yellow-brown tones, which are transformed into a Bordeaux with very good fastness properties after being chromed . The dye is particularly suitable for dyeing wool using the single bath honing process, which also gives very real Bordeaux tones.
In the present process as starting material from N-n-Oct.yl-4-oxy-2-cliino- lon can, for. B. be prepared by condensing o - ("lilorbenzoesäiire finit n-octylamine, <I> the </I> obtained 2-n-Oetylamino-1-benzoic acid and acetylated in the 2-n-Oetyl-aeetyl - i amino -1-beii7oesäure completes the ring closure with elimination of water.
The combination of the N-n-Octy l-4-oxy-2-quino- lons thus obtainable with the diazotized 4-chloro-2-amino-l-oxybenzene-6-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-aniino-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 5 Uncooled solution of 27.3 parts of Nn-octyl-4-oxy 2-eliinolone in 400 parts of water,
4 parts of sodium hydroxide and 25 parts of sodium carbonate were added. The mixture is stirred at 10 to 15 until no more diazo compounds can be detected. The resulting dye is detected by IIinztifüg @ en. completely separated from sodium chloride, filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261368T | 1947-03-14 | ||
| CH267277T | 1947-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267277A true CH267277A (en) | 1950-03-15 |
Family
ID=25730465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267277D CH267277A (en) | 1947-03-14 | 1947-03-14 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267277A (en) |
-
1947
- 1947-03-14 CH CH267277D patent/CH267277A/en unknown
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