CH303545A - 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
- CH303545A CH303545A CH303545DA CH303545A CH 303545 A CH303545 A CH 303545A CH 303545D A CH303545D A CH 303545DA CH 303545 A CH303545 A CH 303545A
- Authority
- CH
- Switzerland
- Prior art keywords
- cobalt
- dye
- azo dye
- dyes
- metal
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 7
- 239000002184 metal Substances 0.000 title claims description 4
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 17
- 229910017052 cobalt Inorganic materials 0.000 claims description 16
- 239000010941 cobalt Substances 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 238000001465 metallisation Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 210000002268 wool Anatomy 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 3
- WHIXQFSPEDIMGL-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=C(Cl)C=C1 WHIXQFSPEDIMGL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 239000012065 filter cake Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Description
Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. Es wurde gefunden, dass man zu einem neuen, wertvollen, metallhaltigen Azofarbstoff gelangt, wenn man auf ein Gemisch der zwei Monoazofarbstoffe, die den folgenden Formeln
EMI0001.0008
entsprechen, kobaltabgebende Mittel derart einwirken lässt, dass ein kobalthaltiger Azo- farbstoff entsteht,
der je ein Molekül der zwei Ausgangsmonoazofarbstoffe an ein Kobalt atom komplex gebunden enthält.
Der neue kobalthaltige Farbstoff bildet ein dunkles Pulver, das sich in Wasser löst und Wolle aus neutralem oder schwach essigsaurem Bade in braunen Tönen färbt.
Die zwei beim vorliegenden Verfahren als Ausgangsstoffe dienenden Monoazofarbstoffe können nach an sich bekannten Methoden hergestellt werden, indem man diazotiertes 9--Amino-l-oxybenzol-4-sulfonsäuremethylamid mit 1-(4'-Chlorphenyl)-3-methyl-5-pyrazolon und diazotiertes 2-Amino-l-oxybenzol-4-sulfon- säuremethylamid mit 1-Acetylamino-7-oxy- naphthalin jeweils in alkalischem Medium kup pelt.
Die Behandlung mit den kobaltabgebenden Mitteln erfolgt gemäss vorliegendem Verfahren 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 Metallisie- rung zweckmässig mit solchen kobaltabgeben- den Mitteln und nach solchen Methoden durch, welche erfahrungsgemäss komplexe Kobaltver- bindungen dieser Zusammensetzung liefern.
Es empfiehlt sich im allgemeinen, auf ein Molekül eines Farbstoffes weniger als ein Atom Kobalt zu verwenden undloder die Me- tallisierung in schwach saurem bis alkalischem Medium auszuführen. Als kobaltabgebende Mittel verwendet man zweckmässig einfache Kobaltsalze, wie Kobaltsulfat oder Kobalt acetat, gegebenenfalls auch frisch gefälltes Kobalthydroxyd.
<I>Beispiel:</I> 21,8 Teile des Farbstoffes aus diazotiertem 2-Amino-l-oxybenzol-A-sulfonsäuremethylamid und 1-(4'-Chlorphenyl)-3-methyl-5-pyrazolon und 20,7 Teile des Farbstoffes aus diazotiertem 2-Amino-l-oxybenzol-4-siilfonsäuremethylamid und 1-Acetylamino-7-oxynaphthalin, beide Farbstoffe in Form einer feuchten Paste (Fil terkuchen), werden in 800 Teilen Wasser unter Zusatz von 8,0 Teilen Natriumhydroxyd gelöst.
Nun wird auf 80 erwärmt und mit 110 Teilen einer Kobaltsulfatlösung mit einem Kobaltgehalt von 2,95 % versetzt. Nach kur zem Erwärmen auf 85 ist die Komplexbildung beendet. Durch Neutralisieren mit verdünnter Essigsäure und Natriumehloridzugabe wird der Farbstoff abgeschieden.
Process for the preparation of a metal-containing azo dye. It has been found that a new, valuable, metal-containing azo dye is obtained by using a mixture of the two monoazo dyes having the following formulas
EMI0001.0008
correspond, lets the cobalt-releasing agent act in such a way that an azo dye containing cobalt is formed,
which contains one molecule of each of the two starting monoazo dyes bound to a cobalt atom in a complex.
The new cobalt-containing dye forms a dark powder that dissolves in water and dyes wool from a neutral or slightly acetic acid bath in brown shades.
The two monoazo dyes used as starting materials in the present process can be prepared by methods known per se by mixing diazotized 9-amino-1-oxybenzene-4-sulfonic acid methylamide with 1- (4'-chlorophenyl) -3-methyl-5-pyrazolone and diazotized 2-amino-1-oxybenzene-4-sulfonic acid methylamide with 1-acetylamino-7-oxynaphthalene in each case in an alkaline medium.
The treatment with the cobalt-releasing agents is carried out 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 metallization is expediently carried out using such cobalt-releasing agents and using methods which, experience has shown, give complex cobalt compounds of this composition.
It is generally advisable to use less than one atom of cobalt per molecule of a dye and / or to carry out the metallization in a weakly acidic to alkaline medium. Simple cobalt salts, such as cobalt sulfate or cobalt acetate, and optionally also freshly precipitated cobalt hydroxide, are expediently used as cobalt-releasing agents.
<I> Example: </I> 21.8 parts of the dye from diazotized 2-amino-1-oxybenzene-A-sulfonic acid methylamide and 1- (4'-chlorophenyl) -3-methyl-5-pyrazolone and 20.7 parts of the dye from diazotized 2-amino-l-oxybenzene-4-siilfonsäuremethylamid and 1-acetylamino-7-oxynaphthalene, both dyes in the form of a moist paste (filter cake), are dissolved in 800 parts of water with the addition of 8.0 parts of sodium hydroxide .
It is now heated to 80 and mixed with 110 parts of a cobalt sulfate solution with a cobalt content of 2.95%. After brief heating to 85, the complex formation is complete. The dye is deposited by neutralizing with dilute acetic acid and adding sodium chloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH301441T | 1951-08-07 | ||
| CH303545T | 1951-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303545A true CH303545A (en) | 1954-11-30 |
Family
ID=25734363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303545D CH303545A (en) | 1951-08-07 | 1951-08-07 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303545A (en) |
-
1951
- 1951-08-07 CH CH303545D patent/CH303545A/en unknown
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