CH306879A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH306879A CH306879A CH306879DA CH306879A CH 306879 A CH306879 A CH 306879A CH 306879D A CH306879D A CH 306879DA CH 306879 A CH306879 A CH 306879A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- parts
- dye
- acid ester
- water
- 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 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 239000000975 dye Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- WLJLENRIPLYJSZ-UHFFFAOYSA-N 2-amino-4-(2-methylbutan-2-yl)-6-nitrophenol Chemical compound CCC(C)(C)C1=CC(N)=C(O)C([N+]([O-])=O)=C1 WLJLENRIPLYJSZ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000012141 concentrate 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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. Gelenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Monoazofarb- stoffes. Das Verfahren ist dadurch gekenn zeichnet, dass man diazotiertes 6-Nitro-2-amino- 4-tert.amyl-phenol mit 1-(2'-Chlor-phenyl)
-5- pyra.zolon - 3 - carbonsäureester - 5'-sulfonsäure- amid kuppelt und die 3-Carbonsäureester- gruppe durch Einwirkung von Methylamin in die 3-Carbonsäuremethylamidgruppe um wandelt.
Der erhaltene neue Farbstoff stellt ein dunkles, violettbraunes Pulver dar, das sich in Wasser mit blaustichig roter, in konz. Schwe felsäure mit braunoranger Farbe löst und Wolle nachehromiert blaustichig rot färbt.
Beispiel: '32,4 Teile 6-Nitro-2-amino-4-tert.aniyl- plienol werden mit 4,1 Teilen Natrium- liycIroxy cl in 200 Teilen Wasser gelöst, 6,9 Teile Natriumnitrit in 35 Teilen Wasser zuge setzt und die Mischung bei einer 3 nicht übersteigenden Temperatur auf 35 Voluniteile 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- lioiisätireät.hy-lester-5'-sulfonsäureamid und 8 Teilen Natriumhydroxyd in<B>100</B> Teilen Was ser von 0-3 zugegeben wird.
Das Reaktions- gemisch wird mit 10 Teilen Ammoniak 25 /o ig 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 21/2 /a gewaschen. Der feuchte Filterkuchen des Farb stoffes wird nun mit 25o/oigem wässerigem Methylamin angeschlämmt und dann 3-4 Tage bei Zimmertemperatur stehengelassen.
Darauf wird mit Kochsalzlösung verdünnt., filtriert und getrocknet. Der so erhaltene Farbstoff stellt ein dunkles, violettbraunes Pul ver dar, das sich in heissem Wasser mit blaustichig roter, in konz. Schwefelsäure mit braunoranger Farbe löst. Der Farbstoff wird zweckmä.ssigerweise mit etwas Natriumkarbonat und einem Dispergiermittel gut vermahlen. Er färbt Wolle aus saurem Bad mit bräun lichgelbem Farbton, der beim Nachchromieren in ein blaustichiges Rot übergeht.
Nach dem Einbadchromverfahren erhält man ohne oder mit nur geringem Säurezusatz unter völliger Erschöpfung des Färbebades nuancen- und stärkegleiche Färbungen, die sehr gute Nass- und Lichtechtheiten aufweisen.
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-amino-4-tert-amyl-phenol with 1- (2'-chloro-phenyl)
-5- pyra.zolon - 3 - carboxylic acid ester - 5'-sulfonic acid amide couples and converts the 3-carboxylic acid ester group into the 3-carboxylic acid methyl amide group by the action of methylamine.
The new dye obtained is a dark, violet-brown powder, which in water turns bluish red, in conc. Sulfur acid dissolves with a brownish-orange color and gives wool a reddish tinge of blue.
Example: '32, 4 parts of 6-nitro-2-amino-4-tert.aniylplienol are dissolved with 4.1 parts of sodium liycIroxy cl in 200 parts of water, 6.9 parts of sodium nitrite in 35 parts of water are added and Concentrate the mixture at a temperature not exceeding 3 to 35 parts by volume. 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 to Congoneutral with sodium bicarbonate, whereupon a solution of 35.5 parts of 1- (2'-chlorophenyl) -5-pyrazolone-3-car- lioiisätireät.hy-lester -5'-sulfonic acid amide and 8 parts of sodium hydroxide in <B> 100 </B> parts of water from 0-3 is added.
The reaction mixture is made slightly alkaline to phenolphthalein with 10 parts of 25% ammonia. Then the temperature is allowed to rise slowly from 3 to 20. The coupling is complete after about 20 hours. The precipitated dye is filtered and washed with brine from 21/2 / a. The moist filter cake of the dye is then slurried with 25% aqueous methylamine and then left to stand for 3-4 days at room temperature.
It is then diluted with saline solution, filtered and dried. The dye thus obtained is a dark, violet-brown powder that turns red in hot water with a bluish tinge, in conc. Sulfuric acid dissolves with a brown-orange color. The dye is conveniently well ground with a little sodium carbonate and a dispersing agent. It dyes wool from an acid bath with a brownish-yellow hue, which turns into a bluish red when it is chromed.
With the single-bath chrome process, dyeings of the same shade and thickness, with very good wet and light fastness properties, are obtained with little or no addition of acid and with complete exhaustion of the dye bath.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH293699T | 1951-07-27 | ||
| CH306879T | 1951-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306879A true CH306879A (en) | 1955-04-30 |
Family
ID=25733411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306879D CH306879A (en) | 1951-07-27 | 1951-07-27 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306879A (en) |
-
1951
- 1951-07-27 CH CH306879D patent/CH306879A/en unknown
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