CH304278A - Process for the production of a cobalt-containing azo dye. - Google Patents
Process for the production of a cobalt-containing azo dye.Info
- Publication number
- CH304278A CH304278A CH304278DA CH304278A CH 304278 A CH304278 A CH 304278A CH 304278D A CH304278D A CH 304278DA CH 304278 A CH304278 A CH 304278A
- Authority
- CH
- Switzerland
- Prior art keywords
- cobalt
- dye
- yellow
- releasing agent
- containing azo
- Prior art date
Links
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims description 21
- 229910017052 cobalt Inorganic materials 0.000 title claims description 19
- 239000010941 cobalt Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 9
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 13
- 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 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001868 cobalt Chemical class 0.000 claims description 2
- 238000001465 metallisation Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229940044175 cobalt sulfate Drugs 0.000 description 2
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 2
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
- 230000009918 complex formation Effects 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
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HLMZZYYGOKOOTA-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=CC=C1Cl HLMZZYYGOKOOTA-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Verfahren zur Herstellung eines kobalthaltigen Azofarbstoffes. Es wurde gefunden, da.ss man zu einem reuen, wertvollen, kobalthaltigen Azofarb- stoff gelangt, wenn man auf den Monoazo- farbstoff der Formel
EMI0001.0009
l:obaltabgebende Mittel derart einwirken lässt, dass ein kobalthaltiger Azofarbstoff entsteht, der zwei Monoazofarbstoffmoleküle an ein Kobaltatom komplex gebunden enthält.
Der neue kobalthaltige Farbstoff stellt ein wasserlösliehes braunes Pulver dar, welches sieh in Schwefelsäure mit orangegelber, in Na- triumearbonatlösung mit gelbbrauner Farbe löst und Wolle aus schwach alkalisehem, neu tralem oder schwach saurem Bade in vollen goldgelben Tönen von guten Echtheiten färbt.
Der als Ausgangsstoff dienende, der oben stehenden Formel entsprechende Monoazo- @arbstoff kann durch Kupplung von 1-Aceto- aeetylamino-2,5-dichlorbenzol mit nach an sieh bekannten Methoden, z. B. mittels Salz säure und Natriumnitrit diazotiertem 2- Amino -1- oxybenzol-4- sulfonsäuremethylamid hergestellt werden.
Die Behandlung mit den kobaltabgeben- den A-litteln erfolgt gemäss vorliegendem Ver- fahren in der Weise, dass ein kobalthaltiger Farbstoff entsteht, der pro Molekül Farb stoff weniger als ein Atom Kobalt in kom plexer Bindung enthält. Demgemäss führt man die Metallisierung zweckmässig mit sol chen kobaltabgebenden Mitteln und nach sol chen Methoden durch, welche erfahrungs gemäss komplexe Kobaltverbindungen dieser Zusammensetzung liefern.
Es empfiehlt sich im allgemeinen, auf ein Molekül eines Farb stoffes weniger als ein, mindestens aber i/2 Atom Kobalt zu verwenden und/oder die ivletallisierung in schwach saurem bis alkali schem Medium auszuführen. Als kobaltabge- bende Mittel verwendet man zweckmässig Ko- baltsalze wie Kobaltsulfat oder Kobaltacetat, gegebenenfalls auch frisch gefälltes Kobalt <B>.</B> ydroxyd.
<I>Beispiel:</I> 4,59 Teile des Farbstoffes aus diazotier- tem 2-.Amino-l-oxybenzol-4-sulfonsäuremethyl- amid und 1-Acetoacetylamino-2,5-dichlorben- zol werden in 300 Teilen Wasser und 2,6 Tei len<B>301</B> / o iger Natriumhydroxydlösung gelöst.
Die auf etwa ,80 erwärmte Lösung wird mit 30 Teilen einer Kobaltsulfatlösung mit einem Kobaltgehalt von 1,18 % versetzt und 30 Mi- nuten bei 80 bis 85 gerührt. Nach dieser Zeit ist die Komplexbildung beendet. Man filtriert heiss und dampft das Filtrat im Vakuum ein.
Process for the production of a cobalt-containing azo dye. It has been found that one arrives at a pure, valuable, cobalt-containing azo dye if one uses the monoazo dye of the formula
EMI0001.0009
l: lets obalt-releasing agent act in such a way that a cobalt-containing azo dye is formed which contains two monoazo dye molecules bound to a cobalt atom in a complex.
The new cobalt-containing dye is a water-soluble brown powder which dissolves in sulfuric acid with orange-yellow, in sodium carbonate solution with yellow-brown color and dyes wool from weakly alkaline, neutral or weakly acidic baths in full golden-yellow shades of good fastness properties.
Serving as the starting material, the above formula corresponding monoazo @ dye can aeetylamino-2,5-dichlorobenzene by coupling 1-aceto with methods known per se, z. B. by means of hydrochloric acid and sodium nitrite diazotized 2-amino -1-oxybenzene-4-sulfonic acid methylamide are produced.
The treatment with the cobalt-releasing agents is carried out according to the present process in such a way that a cobalt-containing dye is produced which contains less than one atom of cobalt in a complex bond per molecule of dye. Accordingly, the metallization is expediently carried out with such cobalt-releasing agents and by such methods which, from experience, yield complex cobalt compounds of this composition.
It is generally advisable to use less than one, but at least ½ atom of cobalt on a molecule of a dye and / or perform the metallicization in a weakly acidic to alkaline medium. Cobalt salts such as cobalt sulfate or cobalt acetate, optionally also freshly precipitated cobalt hydroxide, are expediently used as cobalt-releasing agents.
<I> Example: </I> 4.59 parts of the dye from diazotized 2-amino-l-oxybenzene-4-sulfonic acid methylamide and 1-acetoacetylamino-2,5-dichlorobenzene are dissolved in 300 parts of water and 2.6 parts of <B> 301 </B> / o sodium hydroxide solution dissolved.
The solution, heated to about .80, is mixed with 30 parts of a cobalt sulfate solution with a cobalt content of 1.18% and stirred at 80 to 85 minutes for 30 minutes. After this time, the complex formation is complete. It is filtered hot and the filtrate is evaporated in vacuo.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH301811T | 1951-08-14 | ||
| CH304278T | 1951-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304278A true CH304278A (en) | 1954-12-31 |
Family
ID=25734423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH304278D CH304278A (en) | 1951-08-14 | 1951-08-14 | Process for the production of a cobalt-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH304278A (en) |
-
1951
- 1951-08-14 CH CH304278D patent/CH304278A/en unknown
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