CH233093A - Process for the preparation of a chromable monoazo dye. - Google Patents
Process for the preparation of a chromable monoazo dye.Info
- Publication number
- CH233093A CH233093A CH233093DA CH233093A CH 233093 A CH233093 A CH 233093A CH 233093D A CH233093D A CH 233093DA CH 233093 A CH233093 A CH 233093A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromable
- preparation
- monoazo dye
- dye
- orange
- 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
- 239000000975 dye Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 150000001844 chromium Chemical class 0.000 claims description 2
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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 Darstellung eines ehr omier bar en 3lonoazofarbstoifes. Es wurde gefunden, dass man wertvolle chromierbare Monoazofarbstoffe erhält, wenn man diazotierte 2-Aminophenol-6-sulfonsäu- ren, die in 4-Stellung einen Cycloalkylrest oder einen Alkylrest von 3 bis und mit 8 Kohlenstoffatomen enthalten,
mit Pyrazolo- nen ohne freie Sulfon- und Carbonsäuregrup- pen kuppelt.
Gegenstand vorliegenden Zusatzpatentes ist ein Verfahren zur Herstellung eines chro- mierbaren Monoazofarbstoffes, dadurch ge kennzeichnet, dass man diazotierte 2-Amino- 4-n.butylphenol-6-sulfonsäure mit 1-Phenyl- 3-methyl-5-pyrazolon kuppelt.
Der neue Farbstoff stellt ein dunkelrotes Pulver dar, dessen Lösung in Wasser orange, in Schwefelsäure gelborange gefärbt ist. Er färbt Wolle beim Behandeln mit Chromsal zen in gelbstickig roten Tönen. <I>Beispiel:</I> 24,5 Teile 2-Amino-4-n.butylphenol-6- sulfonsäure (aus 4-n.Butylphenol durch'Sul- fonierung, Nitrierung und Reduktion darge stellt) werden in üblicher Weise indirekt di- azotiert. Die Diazoniumverbindung kuppelt man mit 1'l,
9 Teilen 1-Phenyl-3-methyl-5- pyrazolon in sodaalkalischer Lösung. Nach Beendigung der Farbstoffbildung wird der Farbstoff ausgesalzen, abfiltriert und ge trocknet. Er wird als dunkelrotes Pulver er halten, das sich in Wasser mit oranger, in konzentrierter Schwefelsäure mit gelboranger Farbe löst.
Aus saurem Bade zieht er auf Wolle beim Nachchromieren in gelbstickig roten Tönen mit guten Nass- und Lichtecht- heiten. Färbungen mit den gleichen Eigen schaften werden auch direkt nach dem Ein- badchromierverfahren erhalten.
Process for the representation of an honestly bar en 3lonoazofarbstoifes. It has been found that valuable chromable monoazo dyes are obtained if diazotized 2-aminophenol-6-sulfonic acids which contain a cycloalkyl radical or an alkyl radical of 3 to 8 carbon atoms in the 4-position,
couples with pyrazolones without free sulfonic and carboxylic acid groups.
The subject of the present additional patent is a process for the production of a chromable monoazo dye, characterized in that diazotized 2-amino-4-n-butylphenol-6-sulfonic acid is coupled with 1-phenyl-3-methyl-5-pyrazolone.
The new dye is a dark red powder, the solution of which is orange in water and yellow-orange in sulfuric acid. It dyes wool in yellowish-red shades when treated with chromium salts. <I> Example: </I> 24.5 parts of 2-amino-4-n-butylphenol-6-sulfonic acid (prepared from 4-n-butylphenol by sulfonation, nitration and reduction) are shown indirectly in the usual manner diacotized. The diazonium compound is coupled with 1'l,
9 parts of 1-phenyl-3-methyl-5-pyrazolone in a soda-alkaline solution. After the formation of the dye has ended, the dye is salted out, filtered off and dried. It is obtained as a dark red powder that dissolves in water with an orange color and in concentrated sulfuric acid with a yellow-orange color.
From an acidic bath it pulls on wool when it is re-chromed in yellowish red tones with good wet and light fastness. Colorations with the same properties are also obtained directly after the single chrome plating process.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH230906T | 1942-05-16 | ||
| CH233093T | 1942-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233093A true CH233093A (en) | 1944-06-30 |
Family
ID=25727518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233093D CH233093A (en) | 1942-05-16 | 1942-05-16 | Process for the preparation of a chromable monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH233093A (en) |
-
1942
- 1942-05-16 CH CH233093D patent/CH233093A/en unknown
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