CH306874A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH306874A CH306874A CH306874DA CH306874A CH 306874 A CH306874 A CH 306874A CH 306874D A CH306874D A CH 306874DA CH 306874 A CH306874 A CH 306874A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- monoazo dye
- preparation
- dye
- conc
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 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 10
- 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
- 239000002253 acid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 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
- 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
- IUEBPBUIUJWLGX-UHFFFAOYSA-N 4-ethoxy-2,4-dioxobutanoic acid;sodium Chemical compound [Na].CCOC(=O)CC(=O)C(O)=O IUEBPBUIUJWLGX-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- -1 ethyl pyrazolone carboxylate Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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 Herstellung eines Monoazofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Monoazo- farbstoffes. Das Verfahren ist dadurch ge kennzeichnet, dass man diazotiertes 6-Nitro-2- amino-4-tert.amyl-phenol mit. 1-(2'-Chlor plleM,l)-5-pyrazolon-3-carbonsä.llremethylamid- 5'-sulfonsällreamicl kuppelt.
Der erhaltene neue Farbstoff stellt ein dunkles violettbraunes Pulver dar, das sich in heissem Wasser mit blaustichig roter, in konz. Schwefelsäure mit braunorangen Farbe löst. und Wolle naehehromiert blaustichig rot. färbt.
<I>Beispiel:</I> 22,4 Teile 6-Nitro-2-amino-4-tert.amyl- phenolwerden mit 4,1 Teilen Natriumhydroxyd in 200 Teilen Wasser gelöst und zusammen mit einer Lösung von 6,9 Teilen Natriumnitrit in 35 Teilen Wasser in 25 Volumteil'e Salzsäure konz. und 100 Teile Wasser bei 0-3 einge tropft. Der Diazokörper bildet eine gelb ge färbte Suspension.
Durch Zugabe von etwas Natriumbicarbonat wird nach beendeter Di- azot.ierung die Aeidität der Diazosuspension bis kongoneutral abgestumpft, worauf eine Lösung von 33,5 Teilen 1-(2'-Chlor-phellyl)- 5-pyra zolon-3 - carbonsäuremethyla.mid - 5' - sul- fonsUureamid und 8,1 Teilen Natriumhy droxyd in<B>100</B> Teilen Wasser von 0-3 zugegeben wird.
Das Reaktionsgemisch wird mit etwa 10 Teilen Ammoniak 25o/oig schwach phenol- plithaleinalkaliseh gestellt. Dann lässt man die Temperatur langsam von 3 auf 20 steigen. Nach 20 Stunden ist die Kupplung beendet. Der ausgeschiedene Farbstoff wird abfiltriert und getrocknet. Er stellt ein dunkles violett braunes Pulver dar, das sich in heissem Was ser mit blaustichig roter, in konz. Schwefel säure mit. braunoranger Farbe löst..
Der Farb stoff wird zweckmässigerweise mit etwas Na- triumcarbonat und einem Dispergiermittel gut vermahlen. Er färbt Wolle aus saurem Bad mit brällnliehgelbem Farbton, der beim Nach- chromieren in ein blaustichiges Rot übergeht. Nach dem Einbad'ehromverfahren erhält man ohne oder mit nur geringem Säurezusatz unter völliger Erschöpfung des Färbebades nuancen- und stärkegleiche Färbungen, die sehr gute Nass- und Lichtechtheiten aufweisen.
Das- obenerwähnte Pyra.zolon erhält man z. B., indem man 2-Chlor-l-aminobenzol-5-sul- fonsätireamid (Smp.156-158 ) nach bekann ten Methoden in das entsprechende Hydrazin überführt und dieses mit Natriumoxalessig- säureäthylester zum 1- (2'- Chlor - ph enyl)
- 5 - pyrazolon- 3 -carbonsäureester- 5'-sulfonsäure- amid kondensiert. Das 1-(2'-Chlor-phenyl')
- 5-pyra.zolon-3-carbonsäureäthylester- 5'- sulfon- säureamid wird hierauf in der fünffachen Menge 25 % igem wässerigem Methylamin angesehlämmt und entweder 2 bis 4 Tage bei 20 stehengelassen oder 10-15 Stun den im Druckgefäss auf 80-100 erwärmt. Der Pyrazolon-carbonsäureäthylester geht da bei in Lösung, der Alkoholrest des Esters wird abgespaltet und durch den entspre chenden Amidrest ersetzt.
Process for the preparation of a monoazo dye. The present patent relates to a process for the preparation of a monoazo dye. The process is characterized in that diazotized 6-nitro-2-amino-4-tert.amyl-phenol with. 1- (2'-chlorine plleM, l) -5-pyrazolone-3-carboxylic acid, remethylamide-5'-sulfonsallreamicl.
The new dye obtained is a dark violet-brown powder, which in hot water turns bluish red, in conc. Sulfuric acid dissolves with a brown-orange color. and wool sewn with a bluish tinge of red. colors.
<I> Example: </I> 22.4 parts of 6-nitro-2-amino-4-tert-amylphenol are dissolved with 4.1 parts of sodium hydroxide in 200 parts of water and together with a solution of 6.9 parts of sodium nitrite in 35 parts of water in 25 parts by volume of hydrochloric acid conc. and 100 parts of water at 0-3 are added dropwise. The diazo body forms a yellow colored suspension.
By adding a little sodium bicarbonate, after the end of the azotization, the avidity of the diazo suspension is blunted to Congoneutral, whereupon a solution of 33.5 parts of 1- (2'-chlorophellyl) -5-pyrazolone-3-carboxylic acid methyla.mid - 5 '- Sul- fonsUureamid and 8.1 parts of sodium hydroxide in <B> 100 </B> parts of 0-3 water is added.
The reaction mixture is made with about 10 parts of ammonia 25% weakly phenolplithaleinalkalieh. Then the temperature is allowed to rise slowly from 3 to 20. The coupling has ended after 20 hours. The precipitated dye is filtered off and dried. It is a dark purple-brown powder which, in hot water, has a bluish red tint, in conc. Sulfuric acid with. brown-orange color dissolves ..
The dye is best ground well with a little sodium carbonate and a dispersant. He dyes wool from an acid bath with a bright yellow hue, which turns into a bluish red when chromium is applied. According to the single bath 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, with complete exhaustion of the dye bath.
The above-mentioned Pyra.zolon is obtained z. B. by converting 2-chloro-1-aminobenzene-5-sulphonsätireamid (mp 156-158) according to known methods into the corresponding hydrazine and this with sodium oxaloacetic acid ethyl ester to 1- (2'-chlorine - ph enyl)
- 5 - pyrazolone- 3 -carboxylic acid ester- 5'-sulfonic acid amide condensed. 1- (2'-chloro-phenyl ')
- 5-pyra.zolon-3-carboxylic acid ethyl ester 5'-sulfonic acid amide is then slurried in five times the amount of 25% aqueous methylamine and either left to stand for 2 to 4 days at 20 or 10-15 hours in the pressure vessel at 80-100 warmed up. The ethyl pyrazolone carboxylate goes into solution, the alcohol residue of the ester is split off and replaced by the corresponding amide residue.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH291509T | 1951-07-27 | ||
| CH306874T | 1951-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306874A true CH306874A (en) | 1955-04-30 |
Family
ID=25733108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306874D CH306874A (en) | 1951-07-27 | 1951-07-27 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306874A (en) |
-
1951
- 1951-07-27 CH CH306874D patent/CH306874A/en unknown
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