CH233089A - Process for the preparation of a chromable monoazo dye. - Google Patents
Process for the preparation of a chromable monoazo dye.Info
- Publication number
- CH233089A CH233089A CH233089DA CH233089A CH 233089 A CH233089 A CH 233089A CH 233089D A CH233089D A CH 233089DA CH 233089 A CH233089 A CH 233089A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromable
- preparation
- monoazo dye
- dye
- orange
- Prior art date
Links
- 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 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- GENSTRUCMIZOCD-UHFFFAOYSA-N 5-methyl-2-(2-methylphenyl)-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1C GENSTRUCMIZOCD-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
- 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
- 239000004020 conductor Substances 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
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 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 chromierbaren Monoazofarbstoifes. 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-tert.amylphenol-6-sulfonsäure mit 1-(2'- Methylphenyl)-3-methyl-5-pyrazolon kuppelt.
Der neue Farbstoff stellt ein rotes Pulver dar, dessen Lösung in Wasser orange, in Schwefelsäure gelborange gefärbt ist. Er färbt Wolle beim Behandeln mit Chromsal zen in gelbstichig roten Tönen. <I>Beispiel:</I> 26 Teile 2-Amino-4-tert.amylphenol-6- sulfonsäure (aus 4-tert.-Amylphenol durch Sulfonierung, Nitrierung und Reduktion dar gestellt) werden in üblicher Weise indirekt diazotiert. Die Diazoniumverbindung kuppelt man mit 19,3 Teilen 1-(2'-Methylphenyl)
-3- methyl-5-pyrazolon in sodaalkalischer Lö sung. Nach Beendigung der Farbstoffbildung wird der Farbstoff aasgesalzen, abfiltriert und getrocknet. Er wird als rotes 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 gelbstichig roten .Tönen mit guten Nass- und Lichtecht- ]leiten. Färbungen mit den gleichen Eigen schaften werden auch direkt nach dem Ein badchromierverfahren erhalten.
Process for the preparation of a chromable monoazo dye. 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-tert-amylphenol-6-sulfonic acid is mixed with 1- (2'-methylphenyl) -3-methyl-5- pyrazolone couples.
The new dye is a 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> 26 parts of 2-amino-4-tert-amylphenol-6-sulfonic acid (prepared from 4-tert-amylphenol by sulfonation, nitration and reduction) are diazotized indirectly in the customary manner. The diazonium compound is coupled with 19.3 parts of 1- (2'-methylphenyl)
-3- methyl-5-pyrazolone in soda-alkaline solution. After the formation of the dye has ended, the dye is salted, filtered off and dried. It is obtained as a 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 lightfast] conductors. Colorations with the same properties are also obtained directly after the one-bath chrome plating process.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH233089T | 1942-05-16 | ||
| CH230906T | 1942-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233089A true CH233089A (en) | 1944-06-30 |
Family
ID=25727514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233089D CH233089A (en) | 1942-05-16 | 1942-05-16 | Process for the preparation of a chromable monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH233089A (en) |
-
1942
- 1942-05-16 CH CH233089D patent/CH233089A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH233089A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233094A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233092A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233097A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233088A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233091A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233095A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233096A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233090A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233087A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233093A (en) | Process for the preparation of a chromable monoazo dye. | |
| DE600101C (en) | Process for the production of water-insoluble azo dyes | |
| CH233086A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH233085A (en) | Process for the preparation of a chromable monoazo dye. | |
| DE620344C (en) | Process for the production of azo dyes | |
| DE588524C (en) | Process for the production of chromium-containing azo dyes | |
| DE565824C (en) | Process for the production of chromium-containing azo dyes | |
| CH231891A (en) | Process for the preparation of a monoazo dye. | |
| CH230906A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH228935A (en) | Process for the preparation of a chromable azo dye. | |
| CH265417A (en) | Process for the preparation of a stilbene dye. | |
| CH304389A (en) | Process for the preparation of a yellow monoazo dye. | |
| CH257030A (en) | Process for the production of a metallizable azo dye. | |
| CH180960A (en) | Process for the preparation of an azo dye. | |
| CH257028A (en) | Process for the production of a metallizable azo dye. |