CH304281A - 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
- CH304281A CH304281A CH304281DA CH304281A CH 304281 A CH304281 A CH 304281A CH 304281D A CH304281D A CH 304281DA CH 304281 A CH304281 A CH 304281A
- Authority
- CH
- Switzerland
- Prior art keywords
- cobalt
- dye
- process according
- yellow
- azo dye
- 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 5
- 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
- 238000001465 metallisation Methods 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
- 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 1
- 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
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 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
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 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
- 239000003086 colorant Substances 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
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 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
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines kobalthaltigen Azofarbstofes. Es wurde gefunden, dass man zu einem neuen, wertvollen, kobalthaltigen Azofarbstoff ..;,elangt, wenn man auf den Monoazofarbstoff, der Formel
EMI0001.0008
kobaltabgebende Mittel derart einwirken lässt, dass ein kobalthaltiger Azofarbstoff entsteht, der zwei Monoazofarbstoffmoleküle an ein Kobaltatom komplex gebunden enthält.
Der neue kobalthaltige Farbstoff stellt ein wasserlösliches braunes Pulver dar, welches sieh in Schwefelsäure mit orangegelber, in INa- triumearbonatlösung mit gelbbrauner Farbe löst und .'olle aus schwach alkalischem, neu tralem oder schwach saurem Bade in vollen goldgelben Tönen von guten Eehtheiten färbt.
Der als Ausgangsstoff dienende, der oben stehenden Formel entsprechende hIonoazo- farbstoff kann durch Kupplung von Acet- essigsäureanilid mit nach an sich bekannten Methoden, z. B. mittels Salzsäure und Na triumnitrit diazotiertem 2-Amino-l-oxvbenzol- 4-sulforisäuredimethylamid hergestellt wer den.
Die Behandlung mit den kobaltabgeben- den Mitteln erfolgt gemäss vorliegendem Ver fahren in der Weise, dass ein kobalthaltiger Farbstoff entsteht, der pro Molekül Farbstoff weniger als ein Atom Kobalt in komplexer Bindung enthält. Demgemäss führt man die 1letallisierung zweckmässig mit solchen ko- baltabgebenden Mitteln und nach solchen Me thoden durch, welche erfahrungsgemäss kom plexe Kobaltverbindungen dieser Zusammen setzung liefern.
Es empfiehlt sich im allge meinen, auf ein Molekül eines Farbstoffes weniger als ein, mindestens aber 1/9 Atom Kobalt zu verwenden und/oder die Metalli sierung in schwach saurem bis alkalischem 14Tedium auszuführen. Als kobaltabgebende .Mittel verwendet man zweckmässig Kobalt salze wie Kobaltsulfat oder Kobaltacetat, ge gebenenfalls auch frisch gefälltes Kobalt hydroxyd.
<I>Beispiel:</I> 4,04 Teile des Farbstoffes aus diazotiertem @' -Amino -1- oxybenzol - 4-sulfonsäuredimethyl- amid und Acetessigsäureanilid werden in 300 Teilen Wasser und 2,6 Teilen 30 % iger Na- triumhydroxydlösung gelöst.
Die auf etwa 80 erwärmte Lösung wird mit 30 Teilen einer Kobaltsulfatlösung mit einem Kobaltgehalt von 1,18 % versetzt und 30 Minuten bei 80 bis S5 gerührt. Nach dieser Zeit ist die Kom plexbildung 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 new, valuable, cobalt-containing azo dye ..;, if one goes to the monoazo dye, of the formula
EMI0001.0008
lets cobalt donor 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 that dissolves in sulfuric acid with an orange-yellow color, in sodium carbonate solution with a yellow-brown color, and colors from weakly alkaline, neutral or weakly acidic baths in full golden-yellow tones of good strength.
The hIonoazo dye used as starting material and corresponding to the above formula can be prepared by coupling acetoacetic anilide using methods known per se, eg. B. by means of hydrochloric acid and sodium nitrite diazotized 2-amino-l-oxvbenzene-4-sulforisäuredimethylamid produced who the.
The treatment with the cobalt-releasing agents takes place according to the present method in such a way that a cobalt-containing dye is produced which contains less than one atom of cobalt in complex bond per molecule of dye. Accordingly, the metalization is expediently carried out with such cobalt-releasing agents and by methods which, experience has shown, give complex cobalt compounds of this composition.
It is generally advisable to use less than one, but at least 1/9 atom of cobalt on a molecule of a dye and / or perform the metallization in a weakly acidic to alkaline medium. Cobalt salts such as cobalt sulfate or cobalt acetate, and if necessary freshly precipitated cobalt hydroxide, are expediently used as the cobalt-releasing agent.
<I> Example: </I> 4.04 parts of the dye from diazotized @ '-amino -1-oxybenzene-4-sulfonic acid dimethyl amide and acetoacetic anilide are dissolved in 300 parts of water and 2.6 parts of 30% strength sodium hydroxide solution .
The solution, heated to about 80, is mixed with 30 parts of a cobalt sulphate solution with a cobalt content of 1.18% and stirred for 30 minutes at 80 to S5. After this time, the complex formation is over. 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 | ||
| CH304281T | 1951-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304281A true CH304281A (en) | 1954-12-31 |
Family
ID=25734426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH304281D CH304281A (en) | 1951-08-14 | 1951-08-14 | Process for the production of a cobalt-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH304281A (en) |
-
1951
- 1951-08-14 CH CH304281D patent/CH304281A/en unknown
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