CH306877A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH306877A CH306877A CH306877DA CH306877A CH 306877 A CH306877 A CH 306877A CH 306877D A CH306877D A CH 306877DA CH 306877 A CH306877 A CH 306877A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- carboxylic acid
- monoazo dye
- bluish red
- 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
- 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
- DOIZCTMIPKWRDU-UHFFFAOYSA-N 2-amino-4-tert-butyl-6-nitrophenol Chemical compound CC(C)(C)C1=CC(N)=C(O)C([N+]([O-])=O)=C1 DOIZCTMIPKWRDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 10
- 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
- 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
- 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
- 238000007747 plating Methods 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
- 239000011780 sodium chloride Substances 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-2-a.mino- 4-tert.butyl-phenol mit 1-(2'-Chlor-phenyl)
-5- pyrazolon- 3 - carbonsäureester - 5'-sulfonsäure- amid kuppelt und die 3-Carbonsäureester- gruppe durch Einwirkung von Ammoniak in die 3-Carbonsäureamidgruppe umwandelt.
Der erhaltene neue Farbstoff stellt ein dunkles, violettbraunes Pulver dar, das sieb in Wasser mit blaustichig roter, in konz. Schwefelsäure mit braunoranger Farbe löst und Wolle naehehromiert blaustichig rot färbt.
Beispiel: 21.,0 Teile 6-Nitro-2-aiiiiiio-4-tert.brtt5l- phenol werden mit 4,1 Teilen Natriumhydroxyd in 200 Teilen Wasser gelöst, 6,9 Teile Natrium- nit.rit in 35 Teilen Wasser zugesetzt und die Mischung bei einer 3 nicht übersteigenden Temperatur auf 35 Volumteile konz. Salzsäure in 100 Teilen Wasser getropft.
So erhält man eine grünlichge'lbe Suspension des Diazokör- pers. Nach beendeter Diazotierung wird die Azidität. der Diazosuspension mit Natrium- hikarbonat bis kongoneutral abgestumpft, wor auf eine Lösung von 35,5 Teilen 1-(2'-Clilor- phenyl )
-5-pyrazolon - 3 - carbonsäureäthy lester- 5'-sulfonsäiiirea.mid und 8 Teilen Natrium hydroxyd in 100 Teilen Wasser von 0-3 zu gegeben wird. Das Reaktionsgemisch wird mit 10 Teilen Ammoniak 25o/aig schwach phenol- phtaleinalkälisch gestellt. Dann lä.sst man die Temperatur langsam von 3 auf 20 steigen. Nach etwa 20 Stunden ist die Kupplung be endet. Der ausgeschiedene Farbstoff wird fil triert und mit Sole von 21/2 % . gewaschen.
Der feuchte Filterkuchen des Farbstoffes wird nun mit 25 % igeln wässerigem Ammoniak an- geschlämmt und dann 3-4 Tage bei Zimmer temperatur stehengelassen. Darauf wird mit Kochsalzlösung verdünnt, filtriert und ge trocknet. 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 zweckmässigerweise mit. etwas Natriumkarbonat und einem Disper- giermittel gut vermahlen. Er färbt Wolle aus saurem Bad mit bräunlichgelbem Farbton, der beim Nachchromieren in ein blaustichiges Rot übergeht. Nach dem Einbadehromverfahren erhält. man ohne oder mit nur geringem Säure zusatz unter völliger Erschöpfung des Färbe bades nuancen- und stärkegleiche Färbungen, die sehr gute Nass- und Lichtechtheiten auf weisen.
Additional patent to main patent no. 293699. Process for the production of a monoazo dye. The subject of the present patent is a process for the production of a monoazo dye. The process is characterized in that diazotized 6-nitro-2-a.mino-4-tert-butyl-phenol with 1- (2'-chloro-phenyl)
-5- pyrazolone- 3-carboxylic acid ester - 5'-sulfonic acid amide couples and converts the 3-carboxylic acid ester group into the 3-carboxylic acid amide group by the action of ammonia.
The new dye obtained is a dark, violet-brown powder, the sieve in water with a bluish red, in conc. Sulfuric acid dissolves with a brown-orange color and dyes wool with a bluish tinge when it is near-chromed.
Example: 21.0 parts of 6-nitro-2-aiiiiiio-4-tert.brtt5l-phenol are dissolved with 4.1 parts of sodium hydroxide in 200 parts of water, 6.9 parts of sodium nitrite in 35 parts of water are added and the mixture at a temperature not exceeding 3 to 35 parts by volume of conc. Hydrochloric acid was added dropwise to 100 parts of water.
This gives a greenish-yellow suspension of the diazo body. After the end of the diazotization, the acidity becomes. the diazo suspension with sodium bicarbonate blunted to Congoneutral, whereupon a solution of 35.5 parts 1- (2'-clilorphenyl)
-5-pyrazolon - 3 - carbonsäureäthy lester- 5'-sulfonsäiiirea.mid and 8 parts of sodium hydroxide in 100 parts of 0-3 water is added. The reaction mixture is made weakly phenolphthalein-alkaline with 10 parts of ammonia 250 / aig. Then let the temperature rise slowly from 3 to 20. The coupling is over after about 20 hours. The precipitated dye is filtered and treated with brine of 21/2%. washed.
The moist filter cake of the dye is then slurried with 25% aqueous ammonia and then left to stand for 3-4 days at room temperature. It is then diluted with saline, filtered and dried. The dye obtained in this way is a dark, violet-brown powder, which in hot water turns bluish red, in conc. Dissolves sulfuric acid with a brown-orange color.
The dye is conveniently with. Grind some sodium carbonate and a dispersing agent well. It dyes wool from an acidic bath with a brownish-yellow hue that turns into a bluish red when chromium-plating. Received according to the Einbadehrom method. without or with only a small amount of acid, and with complete exhaustion of the dye bath, dyeings of the same shade and thickness which have very good wet and light fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306877T | 1951-07-27 | ||
| CH293699T | 1951-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306877A true CH306877A (en) | 1955-04-30 |
Family
ID=25733409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306877D CH306877A (en) | 1951-07-27 | 1951-07-27 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306877A (en) |
-
1951
- 1951-07-27 CH CH306877D patent/CH306877A/en unknown
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