CH306878A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH306878A CH306878A CH306878DA CH306878A CH 306878 A CH306878 A CH 306878A CH 306878D A CH306878D A CH 306878DA CH 306878 A CH306878 A CH 306878A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- parts
- acid ester
- monoazo dye
- brown
- 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 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 293699. Verfahren zur Herstellung eines Monoazofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Monoazofarb- stoffes. Das Verfahren ist dadurch gekenn zeichnet, dass man diazotiertes 6-Nitro-\?-amino- 4-tert.amyl-phenol mit 1-(2'-Chlor-phenyl)
-5- py razolon - 3 - earbonsäureester - 5'- su'lfonsäure- amid kuppelt und die 3-Carbonsäureester- gruppe d'ttrch Einwirkung von Ammoniak in die 3-Carl)onsänreamidgruppe -umwandelt.
Der erhaltene neue Farbstoff stellt ein dunkles, violettbraunes Pulver dar, das sich in Wasser mit blaustichig roter, in konz. Sehwefelsäure mit braunoranger Farbe löst und Wolle naehehromiert blaustichig rot färbt.
Beispiel: 22,4 Teile 6-Nitro-2-amino-4-tert.amyl- phenol werden mit. 4,1 Teilen Natrium hydroxyd in 200 Teilen Wasser gelöst, 6,9 Teile Natriumnitrit in 35 Teilen Wasser zu gesetzt, und die Mischung bei einer 3 nicht übersteigenden Temperatur auf 35 Volumteile konz. Salzsäure in 100 Teilen Wasser ge tropft.
So erhält man eine grünlichgelbe Sus pension des Diazokörpers. Nach beendeter Di- azotierung wird die Azidität der Diazosuspen- sion mit Natriumbikarbonat bis kongoneutral abgestumpft, worauf eine Lösung von 35,5 Teilen 1-(2'-Chlor-phenyl)-5-pyrazolon-3-car- bonsäureäthylest.er-5'-sulfonsäureamid und 8 Teilen Natriumhydroxyd in 100 Teilen Wasser von 0-3 zugegeben wird.
Das Reaktionsge- miseh wird mit<B>10</B> 0 Teilen Ammoniak 25o/oig schwach phenolphtaleinalkalisch gestellt. Dann lässt man die Temperatur langsam von 3 auf 20 steigen. Nach etwa 20 Stunden ist die Kupplung beendet. Der ausgeschiedene Farb stoff wird filtriert und mit Sole von 21/21/g gewaschen. Der feuchte Filterkuchen des Farb stoffes wird nun mit. 25,1/o-igem wässerigem Ammoniak angeschlämmt und dann 3-4 Tage bei Zimmertemperatur stehengelassen. Darauf wird mit Koehsalzlösung verdünnt, filtriert und getrocknet.
Der so erhaltene Farbstoff stellt ein dunkles, violettbraunes Pulver dar, das sich in heissem Wasser mit blaustichig- roter, in konz. Schwefelsäure. mit braunoranger Farbe löst. Der Farbstoff wird zweckmässiger weise mit etwas Natriumkarbonat und einem Dispergiermittel gut vermahlen. Er färbt Wolle aus saurem Bad mit bräunlichgelbem Farbton, der beim Naehehromieren in ein blaustichiges Rot übergeht. Nach dem Ein bad,chromverfahren erhält man ohne oder mit.
nur geringem Säurezusatz unter völliger Er schöpfung des Färbebades nuancen- und stärkegleiche Färbungen, die sehr gute Nass- und Lichteehtheiten aufweisen.
Additional patent to main patent no. 293699. Process for the production of a monoazo dye. The present patent relates to a process for the production of a monoazo dye. The process is characterized in that diazotized 6-nitro - \? - amino-4-tert.amyl-phenol with 1- (2'-chloro-phenyl)
-5- py razolon-3-carboxylic acid ester-5'-sulfonic acid amide couples and converts the 3-carboxylic acid ester group into the 3-carboxylic acid ester group under the action of ammonia into the 3-carboxylic acid ester group.
The new dye obtained is a dark, violet-brown powder that turns bluish red in water, in conc. Sulfuric acid dissolves with a brown-orange color and dyes wool with a bluish tinge when it is near-chromed.
Example: 22.4 parts of 6-nitro-2-amino-4-tert.amylphenol are mixed with. 4.1 parts of sodium hydroxide dissolved in 200 parts of water, 6.9 parts of sodium nitrite in 35 parts of water were added, and the mixture was concentrated to 35 parts by volume at a temperature not exceeding 3. Hydrochloric acid was added dropwise to 100 parts of water.
A greenish-yellow suspension of the diazo body is thus obtained. After the end of the diazotization, the acidity of the diazo suspension is blunted with sodium bicarbonate to Congoneutral, whereupon a solution of 35.5 parts of 1- (2'-chlorophenyl) -5-pyrazolone-3-carboxylic acid ethyl ester-5 '-sulfonic acid amide and 8 parts of sodium hydroxide in 100 parts of water from 0-3 is added.
The reaction mixture is made weakly alkaline with phenolphthalein with 10/0 parts of ammonia. Then the temperature is allowed to rise slowly from 3 to 20. The coupling is complete after about 20 hours. The precipitated color is filtered and washed with brine of 21/21 / g. The moist filter cake of the dye is now with. 25.1 / o strength aqueous ammonia slurried and then left to stand for 3-4 days at room temperature. It is then diluted with saline solution, filtered and dried.
The dye obtained in this way is a dark, violet-brown powder, which in hot water turns bluish-red, in conc. Sulfuric acid. dissolves with brown-orange color. The dye is conveniently well ground with a little sodium carbonate and a dispersing agent. He dyes wool from an acidic bath with a brownish-yellow hue, which turns into a bluish red when sewn close. After the one bath, chrome process you get with or without.
only a small amount of acid added with complete exhaustion of the dyebath dyeings of the same shade and thickness, which have very good wetness and lightness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH293699T | 1951-07-27 | ||
| CH306878T | 1951-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306878A true CH306878A (en) | 1955-04-30 |
Family
ID=25733410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306878D CH306878A (en) | 1951-07-27 | 1951-07-27 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306878A (en) |
-
1951
- 1951-07-27 CH CH306878D patent/CH306878A/en unknown
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