CH296531A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH296531A CH296531A CH296531DA CH296531A CH 296531 A CH296531 A CH 296531A CH 296531D A CH296531D A CH 296531DA CH 296531 A CH296531 A CH 296531A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- oxynaphthalene
- violet
- preparation
- monoazo 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 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 2
- 239000000843 powder Substances 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
- 239000000987 azo dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man dianotiertes 4-Nitro 2-amino-l-oxybenzol mit 1- Sulfacetamino - 7 - oxynaphthalin ver einigt.
Der neue Farbstoff stellt ein schwärzliches Pulver dar, das sich in Wasser mit. violetter und in konzentrierter Schwefelsäure mit rosa roter Farbe löst und Wolle aus saurem Bade in violettbraunen Tönen färbt, welche beim Naehchromieren in ein gelbstichiges Oliv von guten Nassechtheiten und vorzüglicher Licht- eehtheit. übergeführt werden.
Das dem vorliegenden Verfahren als Aus- grangsstoff dienende 1-Sulfacetamino-7-oxy- naphthalin kann beispielsweise erhalten wer den, indem man l.-Am ino-7-oxynaphthalin an der Aminogruppe mit Chloressigsäurechlorid monoacyliert und das erhaltene 1-Chlor-ace- tylamino - 7 - oxynaphthalin mit sehwefliger Säure bzw. mit den Salzen dieser Säure um setzt.
Die Kupplung kann nach an sich bekann- ten Methoden, z. B. in alkalischem Medium, erfolgen.
Beispiel <I>;</I> 15,4 Teile 4-Nitro-2-amino-l-oxybenzol werden in 22 Teilen 30%iger Salzsäure und 150 Teilen Wasser suspendiert und bei 5 mit. einer Lösung von 6,9 Teilen 1\Tatriumnitrit in 25 Teilen Wasser dianotiert.
Die so erhaltene Suspension wird mit einer Lösung von 28,1 Teilen 1-Sulfacetamino-7-oxynaphthalin, 4 Tei len Natriumhydroxyd, 5,3 Teilen Natrium- carbonat in 150 Teilen Wasser vermischt und die Kupplung bei 0 bis 5 zu Ende geführt. Nach beendeter Kupplung wird der ausge schiedene Farbstoff durch Filtration abge trennt, mit verdünnter Natriumehloridlösung gewaschen und getrocknet.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if dianotated 4-nitro 2-amino-1-oxybenzene is combined with 1-sulfacetamino-7-oxynaphthalene.
The new dye is a blackish powder that dissolves in water. dissolves violet and in concentrated sulfuric acid with pink-red color and dyes wool from an acid bath in violet-brown tones, which when chromed into a yellowish olive of good wet fastness and excellent lightfastness. be transferred.
The 1-sulfacetamino-7-oxynaphthalene used as the starting material in the present process can be obtained, for example, by monoacylating l.-amino-7-oxynaphthalene on the amino group with chloroacetic acid chloride and the 1-chloro-ace- tylamino - 7 - oxynaphthalene reacts with sulphurous acid or with the salts of this acid.
The coupling can be carried out by methods known per se, e.g. B. in an alkaline medium.
Example <I>; </I> 15.4 parts of 4-nitro-2-amino-1-oxybenzene are suspended in 22 parts of 30% strength hydrochloric acid and 150 parts of water and at 5 with. a solution of 6.9 parts of sodium nitrite in 25 parts of water.
The suspension thus obtained is mixed with a solution of 28.1 parts of 1-sulfacetamino-7-oxynaphthalene, 4 parts of sodium hydroxide, 5.3 parts of sodium carbonate in 150 parts of water and the coupling is completed at 0-5. After the coupling has ended, the dyestuff which has separated out is separated off by filtration, washed with dilute sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292083T | 1950-08-01 | ||
| CH296531T | 1950-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296531A true CH296531A (en) | 1954-02-15 |
Family
ID=25733180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296531D CH296531A (en) | 1950-08-01 | 1950-08-01 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296531A (en) |
-
1950
- 1950-08-01 CH CH296531D patent/CH296531A/en unknown
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