CH310251A - 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
- CH310251A CH310251A CH310251DA CH310251A CH 310251 A CH310251 A CH 310251A CH 310251D A CH310251D A CH 310251DA CH 310251 A CH310251 A CH 310251A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- dye
- azo dye
- preparation
- parts
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002184 metal Substances 0.000 title description 3
- 229910052751 metal Inorganic materials 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 3
- 150000004699 copper complex Chemical class 0.000 claims description 3
- -1 copper tetrammine compound Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical class N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 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
- 230000001335 demethylating effect Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
- C09B45/42—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen metallhaltigen Azofarbstoff ge- langt, wenn man auf den Azofarbstoff der Formel
EMI0001.0007
kupferabgebende Mittel in der Weise ein wirken lässt, dass unter Aufspaltung der Methoxygruppe der ein Atomkomplex gebun denes Kupfer im Farbstoffmolekül enthal tende Kupferkomplex entsteht.
Der neue Farbstoff löst sich mit grau blauer Farbe in Wasser -und färbt Baumwolle in lichtechten, blaustichig grauen Tönen.
Der Farbstoff der obigen Formel wird vorteilhaft in der Weise in die komplexe Kup ferverbindung übergeführt, dass man auf ein Mol Farbstoff etwa die einem Grammatom Kupfer entsprechendeMenge kupferabgebendes Mittel unter solchen Bedingungen einwirken lässt, welche die Umwandlung von o-Oxy-o'- alkoxyazogruppierungen in o,o'-Dioxyazokup- ferkomplexe bewirken. Als kupferabgebende Mittel kommen beispielsweise Kupfertetram- minverbindungen in Betracht, und besonders gute Dienste leistet in manchen Fällen die aus einem Kupfer(II)
-salz wie Kupfersulfat und einem Äthanolamin erhältliche Kupfer tetramminverbindung, wobei- zweckmässig ein Überschuss an Äthanolamin vorhanden sein soll. <I>Beispiel:</I> 30,1 Teile 2-Methyl-4-amino-5-methoxy-4'- oxy-1,1'-azobenzol-3'-carbonsäure werden unter .Zusatz der zur Neutralisation notwendigen Menge Natriumhydroxydlösung in 400 Teilen Wasser gelöst,
mit 7 Teilen Natriumnitrit ver setzt und nach dem Abkühlen auf 10 durch Eingiessen von 30 Teilen 30%iger Salzsäure diazotiert. Nach beendeter Diazotierung ver einigt man die Diazoverbindung mit einer auf 5 bis 10 abgekühlten Lösung aus 39,5 Teilen 2-Phenylamino-S-oxynaphthalin-6,3'-disulfon- säure, 40 Teilen wasserfreiem Natriumearbo- nat, 40 Teilen Pyridin oder Picolin und 200 Teilen Wasser und rührt bis zur Beendigung der Kupplung.
Der Disazofarbstoff wird aus gesalzen, filtriert und getrocknet. Er stellt ein dunkles Pulver dar, welches sich in Was ser mit grauvioletter Farbe löst und Baum wolle in violettgrauen Tönen färbt, die beim Nachkupfern etwas röter werden, wobei die Echtheitseigenschaften, insbesondere die Licht- und Waschechtheit, stark verbessert werden.
Zur Herstellung der komplexen Kupfer verbindung wird der Farbstoff in etwa 2000 Teilen warmem Wasser gelöst, mit einer Lö sung. von 25 Teilen kristallisiertem Kupfer sulfat und 80 Teilen Monoäthanolamin in 100 Teilen Wasser versetzt und 8 bis 10 Sture- s den zum Sieden unter Rückfluss erwärmt.. Unter entmethylierender Kupferung bildet sich der o,o'-Dioxyazokupferkomplex, welcher pro Molekül Farbstoff ein Kupferatom ent- hält. Der Farbstoff wird ausgesalzen, filtriert und getrocknet.
Process for the preparation of a metal-containing azo dye. It has been found that a valuable metal-containing azo dye is obtained if one uses the azo dye of the formula
EMI0001.0007
lets the copper-releasing agent act in such a way that, with splitting of the methoxy group, the copper complex containing an atomic complex of copper in the dye molecule is formed.
The new dye dissolves in water with a gray-blue color and dyes cotton in lightfast, bluish gray tones.
The dye of the above formula is advantageously converted into the complex copper compound in such a way that, for one mole of dye, about the amount of copper donating agent corresponding to one gram atom of copper is allowed to act under such conditions that the conversion of o-oxy-o'-alkoxyazo groups into o, o'-Dioxyazokup- ferkomplexe cause. Copper tetrammine compounds, for example, can be used as copper-releasing agents, and in some cases those made from a copper (II)
-salt such as copper sulfate and an ethanolamine obtainable copper tetrammine compound, whereby- an excess of ethanolamine should be present. <I> Example: </I> 30.1 parts of 2-methyl-4-amino-5-methoxy-4'-oxy-1,1'-azobenzene-3'-carboxylic acid are added with the amount necessary for neutralization Sodium hydroxide solution dissolved in 400 parts of water,
ver with 7 parts of sodium nitrite and diazotized after cooling to 10 by pouring 30 parts of 30% hydrochloric acid. When the diazotization is complete, the diazo compound is combined with a solution, cooled to 5 to 10, of 39.5 parts of 2-phenylamino-S-oxynaphthalene-6,3'-disulfonic acid, 40 parts of anhydrous sodium carbonate, 40 parts of pyridine or picoline and 200 parts of water and stirred until the coupling is complete.
The disazo dye is salted out, filtered and dried. It is a dark powder that dissolves in water with a gray-violet color and colors cotton in violet-gray tones that become a little redder when re-coppering, with the fastness properties, in particular the light and wash fastness, are greatly improved.
To produce the complex copper compound, the dye is dissolved in around 2000 parts of warm water with a solution. of 25 parts of crystallized copper sulfate and 80 parts of monoethanolamine in 100 parts of water and 8 to 10 Sture- s heated to boiling under reflux .. With demethylating coppering, the o, o'-dioxyazo copper complex is formed, which contains one copper atom per molecule of dye - holds. The dye is salted out, filtered and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310251T | 1952-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310251A true CH310251A (en) | 1955-10-15 |
Family
ID=4494120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310251D CH310251A (en) | 1952-11-19 | 1952-11-19 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310251A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0982371A1 (en) * | 1998-08-19 | 2000-03-01 | ILFORD Imaging Switzerland GmbH | Metallized disazo dyes, their preparation and use |
-
1952
- 1952-11-19 CH CH310251D patent/CH310251A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0982371A1 (en) * | 1998-08-19 | 2000-03-01 | ILFORD Imaging Switzerland GmbH | Metallized disazo dyes, their preparation and use |
| US6302949B1 (en) | 1998-08-19 | 2001-10-16 | Ilford Imaging Switzerland Gmbh | Metallized bisazo dyes, their preparation and use |
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