CH306873A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH306873A CH306873A CH306873DA CH306873A CH 306873 A CH306873 A CH 306873A CH 306873D A CH306873D A CH 306873DA CH 306873 A CH306873 A CH 306873A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- parts
- brown
- monoazo dye
- dye
- 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 8
- 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
- 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
- 239000000987 azo dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical class 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
- IDABAEPWKOIGNM-UHFFFAOYSA-N CC[Na].OC(=O)CC(=O)C(O)=O Chemical compound CC[Na].OC(=O)CC(=O)C(O)=O IDABAEPWKOIGNM-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
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 238000006193 diazotization 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
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007634 remodeling Methods 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- ainino-4-tert.ainyl-phenol mit 1-(2'-Chlor- plienyl) - 5-pyrazolon-3-carbonsäLtreamid-5'-sul- fonsäureamid kuppelt.
Der erhaltene neue Farbstoff stellt ein dunkles violettbraunes Pulver dar, das sich in heissem Wasser mit blaustichig roter, in konz. Schwefelsäure mit braunoranger Farbe löst und Wolle naehehromiert blaustichig rot. färbt.
Beispiel: ''2,-1 '-'eile 6-Nitro-2-ainino-l-tert.aniyl- plienol werden mit. 4,1 Teilen Natrium- liydroxyd in 200 Teilen Wasser gelöst und zusammen finit einer Lösung von 6,9 Teilen Natriuinnitrit in 35 Teilen Wasser in 25 Volum- teile Salzsäure konz. und<B>100</B> Teile Wasser bei 0-3 eingetropft. Der Diazokörper bildet eine ,,el.b gefärbte Suspension.
Durch Zugabe von etwas Natriumbicarbonat wird nach beendeter Diazotierung die Acidität der Diazosuspension bis kongoneutral abgestumpft., worauf eine hösung von 32,0 Teilen 1-(2'-Chlor-phenyl)- 5-py razolon-3-earbonsäureamid-5'- sillfonsäure- amid und 8,1 Teilen Natriumhydroxyd in 100 Teilen Wasser von 0-3 zugegeben wird.
Das Reaktionsgemisch wird mit: etwa 10 Teilen Aninionia.k 25o/oig schwach phenolphthalein- alkalisch gestellt. Dann lässt man die Tempe ratur langsam von 3 auf 20 steigen. Nach 20 Stunden ist die Kupplung beendet. Der ausgeschiedene Farbstoff wird abfiltriert und getrocknet. Er 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 Natriumcarbo- nat und einem Dispergiermittel gut vermahlen. Er färbt Wolle aus saurem Bad mit bräi-n- l'ichgelbem Farbton, der beim Nachehromieren 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.
Das obenerwähnte Pyrazolon erhält man z. B., indem man 2-Chlor-l-a.minobenzol-5-sul- fonsäureamid (Smp.156-158 ) nach bekann ten Methoden in das entsprechende Hydrazin überführt und dieses mit Natriumoxalessig- säureäthyl ester zum 1- (2'- Chlor - phenyl) - 5 - pyrazolon-3- carbonsäureester - 5'-sulfonsäure- amid kondensiert.
Das 1-(2'-Chlor-phenyl)-5- pyrazolon- 3 - carbonsäureäthylester- 5'-su#lfon- säureamid wird hierauf in der fünffachen Menge 25o-/o-igem wässerigem Ammoniak ange- schlämmt und entweder 2 bis 4 Tage bei 20 stehengelassen oder 10-15 Stunden im Druck gefäss auf 80-100 erwärmt.
Der Pyra.zolon- earborlsäureäthjester geht. dabei in Lösung, der Alkoholrest des Esters wird abgespaltet und durch den entsprechenden Amidrest er setzt.
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-ainino-4-tert.ainyl-phenol is mixed with 1- (2'-chloroplienyl) -5-pyrazolone-3-carboxylic acid treamid-5'-sul- fonsäureamid couples.
The new dye obtained is a dark violet-brown powder, which in hot water turns bluish red, in conc. Sulfuric acid with a brownish-orange color dissolves and wool nears a bluish tinge of red. colors.
Example: '' 2, -1 '-'eile 6-nitro-2-ainino-l-tert.aniylplienol are mixed with. 4.1 parts of sodium hydroxide dissolved in 200 parts of water and combined together with a solution of 6.9 parts of sodium nitrite in 35 parts of water in 25 parts by volume of concentrated hydrochloric acid. and <B> 100 </B> parts of water dropped at 0-3. The diazo body forms an el.b colored suspension.
By adding a little sodium bicarbonate, the acidity of the diazo suspension is blunted to congoneutral after the end of the diazotization, whereupon a solution of 32.0 parts of 1- (2'-chlorophenyl) - 5-pyrazolon-3-carboxamide-5'-sulfonic acid - Amide and 8.1 parts of sodium hydroxide in 100 parts of water from 0-3 is added.
The reaction mixture is made alkaline with about 10 parts of Aninionia.k 25% weakly phenolphthalein. The temperature is then slowly increased from 3 to 20. The coupling has ended after 20 hours. The precipitated dye is filtered off and dried. It is a dark violet-brown powder that turns bluish red in hot water, in conc. Sulfuric acid dissolves with a brown-orange color.
The dye is expediently 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 remodeling.
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 - with complete exhaustion of the dyebath.
The above-mentioned pyrazolone is obtained, for. B. by converting 2-chloro-la.minobenzene-5-sulphonic acid amide (m.p. 156-158) according to known methods into the corresponding hydrazine and this with ethyl sodium oxaloacetate to 1- (2'-chlorine - phenyl) - 5 - pyrazolone-3-carboxylic acid ester - 5'-sulfonic acid amide condensed.
The 1- (2'-chlorophenyl) -5-pyrazolone-3-carboxylic acid ethyl ester-5'-su # lfonic acid amide is then slurried in five times the amount of 25% aqueous ammonia and either 2 to 4 Left to stand for 20 days or heated to 80-100 in a pressure vessel for 10-15 hours.
The Pyra.zolon-earborläuräthjester goes. in 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 |
|---|---|---|---|
| CH306873T | 1951-07-27 | ||
| CH291509T | 1951-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306873A true CH306873A (en) | 1955-04-30 |
Family
ID=25733107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306873D CH306873A (en) | 1951-07-27 | 1951-07-27 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306873A (en) |
-
1951
- 1951-07-27 CH CH306873D patent/CH306873A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH306874A (en) | Process for the preparation of a monoazo dye. | |
| DE341266C (en) | Process for the preparation of related disazo dyes | |
| CH306876A (en) | Process for the preparation of a monoazo dye. | |
| CH306875A (en) | Process for the preparation of a monoazo dye. | |
| CH306880A (en) | Process for the preparation of a monoazo dye. | |
| DE883021C (en) | Process for the preparation of chromable monoazo dyes | |
| CH306877A (en) | Process for the preparation of a monoazo dye. | |
| CH306878A (en) | Process for the preparation of a monoazo dye. | |
| AT82760B (en) | Method for the preparation of stain-coloring leukotriarylmethanazo dyes. | |
| CH306879A (en) | Process for the preparation of a monoazo dye. | |
| DE318997C (en) | Process for the production of leukotriarylmethanazo stain-coloring dyes | |
| CH294946A (en) | Process for the preparation of a monoazo dye. | |
| CH294947A (en) | Process for the preparation of a monoazo dye. | |
| CH240114A (en) | Process for the preparation of a water-soluble disazo dye. | |
| CH306881A (en) | Process for the preparation of a monoazo dye. | |
| CH302390A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH240113A (en) | Process for the preparation of a water-soluble disazo dye. | |
| CH298034A (en) | Process for the preparation of a monoazo dye. | |
| CH230206A (en) | Process for the preparation of a trisazo dye. | |
| CH302389A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH189051A (en) | Process for the preparation of a monoazo dye. | |
| CH132803A (en) | Process for the preparation of a stain dye. | |
| CH290783A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH299203A (en) | Process for the preparation of a monoazo dye. | |
| CH276720A (en) | Process for the preparation of an azo dye. |