CH310690A - 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
- CH310690A CH310690A CH310690DA CH310690A CH 310690 A CH310690 A CH 310690A CH 310690D A CH310690D A CH 310690DA CH 310690 A CH310690 A CH 310690A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- dye
- complex
- azo dye
- atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 6
- 229910052751 metal Inorganic materials 0.000 title description 3
- 239000002184 metal Substances 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 17
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052804 chromium Inorganic materials 0.000 claims description 16
- 239000011651 chromium Substances 0.000 claims description 14
- 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 8
- 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
- 239000002253 acid Substances 0.000 claims description 5
- 150000001845 chromium compounds Chemical class 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000003763 carbonization Methods 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
- 230000015572 biosynthetic process Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- -1 chromium salicylic acid potassium Chemical compound 0.000 description 1
- 238000005254 chromizing Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 301442. Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. Es wurde gefunden, dass man zu einem neuen, wertvollen, metallhaltigen Azofarbstoff gelangt, wenn man auf den Monoazofarbstoff der Formel
EMI0001.0005
chromabgebende Mittel derart einwirken lässt, dass ein chromhaltiger Azofarbstoff entsteht, der zwei Monoazofarbstoffmoleküle an ein Chromatom komplex gebunden enthält.
Der neue Farbstoff bildet ein wasserlös liches Pulver, das Wolle aus schwaeh alkali schem, neutralem oder essigsaurem Bade in blauen Tönen von ausgezeichneter '\Vasch-, Dekatur- und Carbonisierechtheit färbt.
Der als Ausgangsstoff dienende, der oben stehenden Formel entsprechende Monoazofarb- stoff kann durch Kupplung des 5,8-Dichlor- 1-oxy naphthalins mit nach an sich bekannten Methoden, z. B. mittels Salzsäure und Na triumnitrit dianotiertem 4-112ethy1-2-amino-l- oxybenzol-5-sulfonsäureamid hergestellt wer den.
Die Behandlung mit den chromabgebenden Mitteln erfolgt, wie bereits erwähnt, in der Weise, dass ein chromhaltiger Farbstoff ent- steht, der zwei Ivlonoazofarbstoffmoleküle an ein Atom Chrom komplex gebunden enthält. Demgemäss führt man die Chromierung zweck mässig mit solchen chromabgebenden Mitteln. und nach solchen Methoden durch, welche er fahrungsgemäss komplexe Chromverbindungen dieser Zusammensetzung liefern.
Es empfiehlt sich im allgemeinen, auf ein Molekül eines Farbstoffes weniger als ein, mindestens aber ein halbes Atom Chrom zu verwenden undloder die Chromierung in schwach saurem bis alkali- schem Medium auszuführen. Demzufolge sind auch diejenigen Chromverbindungen, die in alkalischem Medium beständig sind, für die Durchführung des Verfahrens besonders gut geeignet, wie z. B. solche Chromverbindungen aliphatischer Oxycarbonsäuren oder vorzugs weise aromatischer o-Oxycarbonsäuren, welche das Chrom in komplexer Bindung enthalten.
Die Metallisierung geschieht mit Vorteil in der Wärme, offen oder unter Druck, z. B. bei Siedetemperatur des Reaktionsgemisches, ge gebenenfalls in Anwesenheit geeigneter Zu sätze, z. B. in Anwesenheit von Salzen organi scher Säuren, von Basen, organischen Lösungs mitteln oder weiteren die Komplexbildung för dernden Mitteln. <I>Beispiel:
</I> 20,2 Teile 4-Methyl-2-amino-l-oxybenzol-5- sulfonsäureamid werden in üblicher Weise in Gegenwart von 16 Teilen 30%-iger Salzsäure mit 7 Teilen Natriumnitrit dianotiert.
Die er- haltene Suspension der Diazoverbindung wird unter gutem Rühren zu einer auf 10 gekühl ten Lösung aus 22,6 Teilen 5,8-Dichlor-l-oxy- naphthalin, 9,6 Teilen Natriumhydroxyd und 200 Teilen Wasser zufliessen gelassen.
Das Kupplungsgemisch wird 20 Stunden bei Raum temperatur gerührt und der ausgeschiedene Farbstoff abfiltriert. Der Filterrückstand wird in verdünnter Natriumhydroxydlösung bei 50 gelöst, die Lösung von eventuellen Ver unreinigungen abfiltriert und der Farbstoff aus dem Filtrat durch Neutralisation mit ver dünnter Salzsäure abgeschieden und abfil- triert. Er stellt getrocknet eine dunkelgefärbte Substanz dar,
die sich in verdünnter Natrium- hy droxy dlösung mit rotvioletter und in kon zentrierter Schwefelsäure mit blaugrüner Farbe löst und Wolle aus essigsaurem Bade in rotvioletten Tönen färbt.
43,2 Teile eines nach vorstehenden An gaben hergestellten Farbstoffes werden in 500 Teilen heissem Wasser unter Zusatz von 6 Teilen Natriumhydroxyd gelöst. Nach Zugabe von 140 Teilen einer Lösung von chromsali- cylsaurem Kalium(Natrium mit einem Chrom- gehalt von 2,6% wird das Chromiergemisch eine Stunde unter Rückfluss gekocht.
Der ge bildete Chromkomplex wird durch Zusatz von Natriumchlorid abgeschieden.
Additional patent to the main patent No. 301442. 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 using the monoazo dye of the formula
EMI0001.0005
lets chromium-releasing agents act in such a way that a chromium-containing azo dye is formed which contains two monoazo dye molecules bound to a chromium atom in a complex.
The new dye forms a water-soluble powder that dyes wool from a weakly alkaline, neutral or acetic acid bath in blue shades that are extremely fast to washing, decaturation and carbonization.
Serving as the starting material, the above formula corresponding monoazo dye can naphthalene by coupling the 5,8-dichloro-1-oxy with methods known per se, for. B. by means of hydrochloric acid and sodium nitrite dianotized 4-112ethy1-2-amino-l-oxybenzene-5-sulfonic acid amide produced who the.
The treatment with the chromium-releasing agents takes place, as already mentioned, in such a way that a chromium-containing dye is produced which contains two ivlonoazo dye molecules bound to one atom of chromium in a complex. Accordingly, the chromizing is carried out appropriately with such chromium-releasing agents. and by methods which, according to experience, deliver complex chromium compounds of this composition.
It is generally advisable to use less than one, but at least half an atom of chromium on a molecule of a dye and / or carry out the chromation in a weakly acidic to alkaline medium. Accordingly, those chromium compounds that are stable in an alkaline medium are particularly well suited for carrying out the process, such as. B. such chromium compounds of aliphatic oxycarboxylic acids or preferably, aromatic o-oxycarboxylic acids, which contain the chromium in a complex bond.
The metallization takes place with advantage in the heat, open or under pressure, z. B. at the boiling point of the reaction mixture, ge where appropriate in the presence of suitable additives to, for. B. in the presence of salts of organic shear acids, bases, organic solvents or other agents promoting the complex formation. <I> example:
</I> 20.2 parts of 4-methyl-2-amino-1-oxybenzene-5-sulfonic acid amide are dianotized with 7 parts of sodium nitrite in the usual manner in the presence of 16 parts of 30% strength hydrochloric acid.
The resulting suspension of the diazo compound is allowed to flow into a solution of 22.6 parts of 5,8-dichloro-1-oxynaphthalene, 9.6 parts of sodium hydroxide and 200 parts of water, cooled to 10, with thorough stirring.
The coupling mixture is stirred for 20 hours at room temperature and the dyestuff which has separated out is filtered off. The filter residue is dissolved in dilute sodium hydroxide solution at 50, the solution is filtered to remove any impurities and the dye is separated from the filtrate by neutralization with dilute hydrochloric acid and filtered off. When dried it is a dark colored substance,
which dissolves in dilute sodium hydroxide solution with red-violet and in concentrated sulfuric acid with a blue-green color and dyes wool from acetic acid bath in red-violet shades.
43.2 parts of a dye prepared as described above are dissolved in 500 parts of hot water with the addition of 6 parts of sodium hydroxide. After adding 140 parts of a solution of chromium salicylic acid potassium (sodium with a chromium content of 2.6%, the chromating mixture is refluxed for one hour.
The chromium complex formed is deposited by adding sodium chloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH301442T | 1952-07-01 | ||
| CH310690T | 1952-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310690A true CH310690A (en) | 1955-10-31 |
Family
ID=25734379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310690D CH310690A (en) | 1952-07-01 | 1952-07-01 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310690A (en) |
-
1952
- 1952-07-01 CH CH310690D patent/CH310690A/en unknown
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