CH301653A - Process for the preparation of a metal-containing azo dye. - Google Patents
Process for the preparation of a metal-containing azo dye.Info
- Publication number
- CH301653A CH301653A CH301653DA CH301653A CH 301653 A CH301653 A CH 301653A CH 301653D A CH301653D A CH 301653DA CH 301653 A CH301653 A CH 301653A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- dye
- atom
- azo dye
- complex
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 6
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 239000002184 metal Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 16
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052804 chromium Inorganic materials 0.000 claims description 14
- 239000011651 chromium Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 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 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001845 chromium compounds Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. 1:s wurde gefunden, dass man zu einem neuen, wertvollen metallhaltigen Azofarbstoff gelangt, wenn man auf den Monoazofarbstoff der Formel
EMI0001.0010
chromabgebende Mittel derart einwirken lässt, (lass ein chromhaltiger Azofarbstoff entsteht,
der zwei Monoazofarbstoffmoleküle an ein Chromatom komplex gebunden enthält.
Der neue Farbstoff bildet ein braunrotes Pulver, das sieh in Wasser mit orangeroter Farbe löst und Wolle aus neutralem bis essim- s < mrein Bade in seliarlaehroten Tönen färbt.
Der als Ausgangsstoff dienende, der oben- stehenden Formel entsprechende Monoazo- farbstoff kann durch Kupplung des 1-(2',5'- Diehlorphenyl) - 3 - methyl - 5 - py razolons mit naeli an sieh bekannten Methoden, z.
B. mit- 1 els Salzsäure und Natriumnitrit, diazotiertem 2-Amirio-l-oxpbenzol-5-sulfonsäiireamid her werden.
Die Behandlung mit den ehromabgeben- den Mitteln erfolgt, wie bereits erwähnt, in der Weise, dass ein chromhaltiger Farbstoff i entsteht, der zwei Monoazofarbstoffmoleküle :m ein Atom Chrom komplex gebunden ent hält. Demgemäss führt man die Cliromierung zweckmässig mit, solchen chromabgebenden Mitteln und nach solchen Methoden durch, welche erfahrungsgemäss komplexe Chromver bindungen dieser Zusammensetzung liefern.
Es empfiehlt sich im allgemeinen, auf ein Molekül eines Farbstoffes weniger als ein Atom Chrom zu verwenden und/oder die Chromierung in sehwach saurem bis alkali schem Medium auszuführen. Demzufolge sind auch diejenigen Chromverbindungen, die in alkalischem Medium beständig sind, für die Durchführung des Verfahrens besonders gut geeignet, wie z. B. solche Chromverbindungen aliphatiseher Oxycarbonsäiiren oder vorzugs weise aromatischer a-Oxycarbonsäuren, welche das Chrom in komplexer Bindung enthalten.
Die Metallisierung geschieht. mit Vorteil in der Wärme, offen oder unter Druck, z. B. bei Siedetemperatur des Reaktionsgemisches, ge gebenenfalls in Anwesenheit geeigneter Zu sätze, z. B. in Anwesenheit von Salzen organi scher Säuren, von Basen, organischen Lö sungsmitteln oder weiteren die Komplexbil dung fördernden Mitteln.
Beispiel: 1.8,8 Teile 2 ;Amino-l-oxybenzol-5-sulfon- säureamid werden in 50 Teilen Nasser und 14 Teilen 30%iger Salzsäure gelöst und bei 0 bis 5 mit einer wässerigen Lösung von 6,9 Teilen Natriumnitrit dianotiert.
Die mit Na- triumearbonat neutralisierte Diazosuspension wird bei 10 bis 12 in eine Lösung aus 24,4 Teilen 1- (2',5'-Dielilorphenyl) - 3-metliyl-5- pyrazolon, 50 Teilen Wasser und 14,0 Teilen 30%igei- Natriumhydroxydlösung eingegos- sen. Die Kupplung verläuft sehr rasch. Der Farbstoff wird durch Hinzufügen von Na- triumehlorid vollständig abgeschieden.
Die dureli Abfiltrieren gewonnene Farhstoffpaste wird in 250 Teilen Wasser verrührt und mit 120 Teilen einer Lösung von eliromsalicylsau- rem Natrium/Kalium mit. einem Chromgehalt von 2,6% sowie 6,7 Teilen 30%igei- Nat.rium- hydroxydlösung versetzt.
Das Ganze wird 3 Stunden am \Rüekfluss gekocht. Naeli dieic-i- Zeit ist die Chromierung beendet. Der ehrom- ha.ltige Farbstoff wird durch Eindampfen des Re aktionsgemisehes im Vakuum isoliert.
Process for the production of a metal-containing azo dye. 1: It has been found that a new, valuable metal-containing azo dye is obtained by using the monoazo dye of the formula
EMI0001.0010
lets chromium-releasing agents act in such a way (let an azo dye containing chromium arise
which contains two monoazo dye molecules bound to a chromium atom in a complex.
The new dye forms a brown-red powder, which dissolves in water with an orange-red color and dyes wool from neutral to essim- s <mrein bath in seliarla-red tones.
The monoazo dye which serves as the starting material and corresponds to the above formula can be prepared by coupling the 1- (2 ', 5'-diehlophenyl) -3-methyl-5-pyrazolone with methods known per se, eg.
B. with 1 els hydrochloric acid and sodium nitrite, diazotized 2-Amirio-1-oxpbenzene-5-sulfonic acid amide.
As already mentioned, the treatment with the e-atom-releasing agents is carried out in such a way that a chromium-containing dye is formed which contains two monoazo dye molecules: one atom of chromium bound in a complex. Accordingly, the Cliromierung is expediently carried out with such chromium-releasing agents and by such methods which, experience has shown, provide complex chromium compounds of this composition.
It is generally advisable to use less than one atom of chromium on a molecule of a dye and / or to carry out the chromating in a slightly acidic to alkaline medium. Accordingly, those chromium compounds that are stable in an alkaline medium are particularly well suited for carrying out the process, such as. B. such chromium compounds aliphatic oxycarboxylic acids or preferably, aromatic α-oxycarboxylic acids, which contain the chromium in a complex bond.
The metallization happens. with advantage in the heat, open or under pressure, z. B. at the boiling point of the reaction mixture, ge where appropriate in the presence of suitable additives to, for. B. in the presence of salts of organic acids, bases, organic solvents or other means that promote the complex formation.
Example: 1.8.8 parts of 2, amino-1-oxybenzene-5-sulfonic acid amide are dissolved in 50 parts of water and 14 parts of 30% hydrochloric acid and dianotized at 0 to 5 with an aqueous solution of 6.9 parts of sodium nitrite.
The diazo suspension neutralized with sodium carbonate is poured into a solution of 24.4 parts of 1- (2 ', 5'-dielilophenyl) -3-methyl-5-pyrazolone, 50 parts of water and 14.0 parts of 30% at 10 to 12 igei- sodium hydroxide solution poured in. The coupling is very quick. The dye is completely deposited by adding sodium chloride.
The dye paste obtained by filtering off is stirred into 250 parts of water and mixed with 120 parts of a solution of eliromsalicylic acid sodium / potassium. a chromium content of 2.6% and 6.7 parts of 30% sodium hydroxide solution.
The whole thing is boiled for 3 hours on the river. Naeli dieic-i-time the chroming is finished. The honest dye is isolated by evaporating the reaction mixture in vacuo.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH298511T | 1951-07-18 | ||
| CH301653T | 1951-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301653A true CH301653A (en) | 1954-09-15 |
Family
ID=25733989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301653D CH301653A (en) | 1951-07-18 | 1951-07-18 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH301653A (en) |
-
1951
- 1951-07-18 CH CH301653D patent/CH301653A/en unknown
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