CH301659A - 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
- CH301659A CH301659A CH301659DA CH301659A CH 301659 A CH301659 A CH 301659A CH 301659D A CH301659D A CH 301659DA CH 301659 A CH301659 A CH 301659A
- Authority
- CH
- Switzerland
- Prior art keywords
- cobalt
- dye
- metal
- parts
- atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000002184 metal Substances 0.000 title claims description 4
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 16
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 15
- 229910017052 cobalt Inorganic materials 0.000 claims description 13
- 239000010941 cobalt 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 6
- 238000001465 metallisation Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001868 cobalt Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000004552 water soluble powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001869 cobalt compounds Chemical class 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
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 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
- 230000009918 complex formation Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J25/00—Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
- H01J25/50—Magnetrons, i.e. tubes with a magnet system producing an H-field crossing the E-field
- H01J25/52—Magnetrons, i.e. tubes with a magnet system producing an H-field crossing the E-field with an electron space having a shape that does not prevent any electron from moving completely around the cathode or guide electrode
- H01J25/58—Magnetrons, i.e. tubes with a magnet system producing an H-field crossing the E-field with an electron space having a shape that does not prevent any electron from moving completely around the cathode or guide electrode having a number of resonators; having a composite resonator, e.g. a helix
- H01J25/587—Multi-cavity magnetrons
Description
Zusatzpatent zum Haaptpatent Nr. <B>298511.</B> Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. Es wurde geftinden, dass man zu einem neuen, wertvollen metallhaltigen Azofarbstoff gelangt, wenn man auf den Monoazofarbstoff der Formel
EMI0001.0009
kobaltabgebende Mittel derart einwirken lässt, dass ein kobalthaltiger Azolarbstoff entsteht,
der zwei Monoazofarbstoffmoleküle an ein 1-#obaltatom komplex gebunden enthält.
Der neue Farbstoff bildet ein wasserlösli- ehes Pulver, das Wolle aus neutralem bis essig saurem Bade in braungelben Tönen färbt.
Der als Ausgangsstoff dienende, der oben- .stehenden Formel entsprechende Monoazofarb- stoff kann durch Kupplung des 1-(4-Chlor- 1)lietivi)-3-meth.v1-5-pyrazolons mit nach all .sieh bek-annten Methoden, z. B. mittels Salz säure und Natriumnitrit, dia7otiertem 2- Amino-6-ehlor-1 -oxybenzol- 4<B>-</B> sullonsäureamid her-estellt werden.
Die Behandlung mit den kobaltabgebenden Mitteln erfolgt gemäss vorliegendem Verfah- peil in der)Veise, dass ein kobalthaltiger Farb stoff entstellt, der pro Molekül Farbstoff we niger als ein Atom Kobalt in komplexer Bin- clung enthält.
Demgemäss führt man die Me- tallisierung zweekmässig mit solehen kobalt- # -ib, -ebenden Mitteln und naeli solchen Metho- den durch, welche erfahrungsgemäss komplexe Kobaltverbindungen dieser Zusammensetzung liefern.
Es empfiehlt sieh im allgemeinen, auf ein Molekül eines Parbstoffes weniger als ein Ntom Kobalt zu verwenden und/oder die Me- tallisierung in schwach saurein bis alkalischem Medium auszuführen. Als kobaltabgebende Mittel verwendet man zweckmässig Kobalt- salze wie Kobaltsulfat oder Kobaltacetat, ge gebenenfalls auch frisell gefälltes Kobalt- hydroxyd.
<I>Beispiel:</I> 22,2 Teile 2-Amino-6-chlor-l-oxybenzol-4- sulionsä-Lireamid werden in<B>50</B> Teilen Wasser und 14 Teilen 301/oiger Natriumhydroxyd- lösung gelöst und nach Zugabe einer wässeri gen Lösung von<B>6,9</B> Teilen Natriumnitrit auf ein Gemisch von<B>28</B> Teilen<B>30</B> 1/9 iger Salzsäure und Eis gegossen.
Die mit Natriumearbonat neutralisierte Diazosuspension wird bei<B>10</B> bis 120 in eine Lösung aus 21 Teilen 1-(41-Chlor- phenvj-3-methyl-5-pyrazolon, <B>50</B> Teilen Was ser und 14,0 Teilen 301/oiger Natrium- bydroxydlösung eingegossen. Die Kupplung verläuft sehr raseli. Der Farbstoff wird dureh Hinzufügen von Natriumehlorid abgesehieden.
4,07 Teile des so erhältliehen Farbstoffes werden als feueliter Filterhuehen in<B>100</B> Teilen Wasser aufgesehlämmt und dureh Zugabe von <B>5</B> Volumteilen 2n<B>-</B> Natriumhydroxydlösung und Erwärmen gelöst.
Die etwa<B>800</B> warme Farbstofflösung versetzt man mit<B>1,5</B> Teilen kristallisiertem Natriumacetat und hieraur mit<B>30</B> Teilen einer<B>70"</B> warmen Kobaltsulfat- lösung mit einem Kobaltgehalt von 1,3%. Naeh kurzer Zeit ist die K omplexbildung be endet,
und die Kobaltverbindun- des Farb- #n stoffes kann dureh Zugabe von Natriumehlo- rid und verdünnter Essigsäure abgeschieden werden.
Additional patent to main patent no. <B> 298511. </B> Process for the production of a metal-containing azo dye. It has been found that a new, valuable metal-containing azo dye is obtained by referring to the monoazo dye of the formula
EMI0001.0009
lets cobalt-releasing agents act in such a way that an azo substance containing cobalt is formed,
which contains two monoazo dye molecules bound to a 1- # obalt atom in a complex.
The new dye forms a water-soluble powder that dyes wool from neutral to acetic acid baths in brown-yellow shades.
The monoazo dye used as the starting material and corresponding to the above formula can be obtained by coupling the 1- (4-chloro-1) lietivi) -3-meth.v1-5-pyrazolone with all known methods, z. B. by means of hydrochloric acid and sodium nitrite, doped 2-amino-6-chloro-1 -oxybenzene- 4 <B> - </B> sulphonic acid amide.
The treatment with the cobalt-releasing agents is carried out according to the present method in the manner that a cobalt-containing dye is distorted which contains less than one atom of cobalt in complex bonds per molecule of dye.
Accordingly, the metallization is carried out in two ways with such cobalt- # -ib, cobalt-emitting agents and only those methods which, experience has shown, yield complex cobalt compounds of this composition.
It generally recommends using less than one atom of cobalt per molecule of a paraffin and / or performing the metallization in a weakly acidic to alkaline medium. Cobalt salts such as cobalt sulfate or cobalt acetate are expediently used as cobalt-releasing agents, and if necessary also cobalt hydroxide precipitated by frisell.
<I> Example: </I> 22.2 parts of 2-amino-6-chloro-1-oxybenzene-4-sulionsä-lireamide are added to <B> 50 </B> parts of water and 14 parts of 301% sodium hydroxide solution and after adding an aqueous solution of <B> 6.9 </B> parts of sodium nitrite to a mixture of <B> 28 </B> parts of <B> 30 </B> 1/9 strength hydrochloric acid and ice poured.
The diazo suspension neutralized with sodium carbonate is converted into a solution of 21 parts of 1- (41-chlorophenvj-3-methyl-5-pyrazolone, 50 parts of Was Water and 14.0 parts of 301% sodium hydroxide solution are poured in. The coupling proceeds very rapidly. The dye is separated out by adding sodium chloride.
4.07 parts of the dye obtained in this way are slurried as feueliter filter faucets in 100 parts of water and dissolved by adding 5 parts by volume of 2N sodium hydroxide solution and heating .
The approximately <B> 800 </B> warm dye solution is mixed with <B> 1.5 </B> parts of crystallized sodium acetate and <B> 30 </B> parts of a <B> 70 "</B> warm cobalt sulphate solution with a cobalt content of 1.3%. The complex formation is over after a short time,
and the cobalt compound of the dye can be deposited by adding sodium chloride and dilute acetic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH298511T | 1951-07-18 | ||
| CH301659T | 1951-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301659A true CH301659A (en) | 1954-09-15 |
Family
ID=25733995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301659D CH301659A (en) | 1951-07-18 | 1951-07-18 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH301659A (en) |
-
1951
- 1951-07-18 CH CH301659D patent/CH301659A/en unknown
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