CH302155A - Process for the preparation of a chromium-containing azo dye. - Google Patents
Process for the preparation of a chromium-containing azo dye.Info
- Publication number
- CH302155A CH302155A CH302155DA CH302155A CH 302155 A CH302155 A CH 302155A CH 302155D A CH302155D A CH 302155DA CH 302155 A CH302155 A CH 302155A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- azo dye
- containing azo
- parts
- compound
- Prior art date
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 11
- 229910052804 chromium Inorganic materials 0.000 title claims description 11
- 239000011651 chromium Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- -1 monoazo compound Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 4
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000001465 metallisation Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines chromhaltigen Azofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines chrom- haltigen Azofarbstoffes, welches darin be steht, dass man 1 Mol der Diazoverbindung aus 1-Oxy-2-aminobenzol-4-sulfonsäureme- thylamid mit 1 Mol 1-Carbo-n-propoxyamino- 7-oxynaphthahn kuppelt und die erhaltene Monoazoverbindung mit einem chromabge benden Mittel behandelt.
Das Verfahren führt zu einem Farbstoff, welcher auf 2 Moleküle Monoazoverbindung weniger als 2 Atome Chrom enthält. Man setzt deshalb mit Vor teil zur Metallisierung der erfindungsgemässen Monoazoverbindung weniger als 2 Atome Chrom je 2 Moleküle Monoazoverbindung ein.
Im nachfolgenden Beispiel bedeuten die 'feile Gewichtsteile und die Prozente Ge wichtsprozente.
<I>Beispiel:</I> 20 Teile 1-Oxy-2-aminobenzol-4-sulfon- säuremethylamid werden in einem Gemisch aus 22 Teilen konzentrierter Salzsäure und 220 Teilen Wasser gelöst und in Lösung bei 0-2' durch Zusatz einer konzentrierten wässe rigen Lösung aus<B>6,9</B> Teilen Natriumnitrit diazotiert. Die gebildete Diazosuspension wird in eine auf 0-2 gekühlte Lösung aus 24 Tei len 1-Carbo-n-propoxyamino-7-oxynaphtha- lin, 14 Teilen 30%iger Natriumhydroxydlö- sung,
20 Teilen Natriumcarbonat und 670 Tei len Wasser zulaufen gelassen. Man setzt der Kupplungsmasse hierauf bei 0-2 innerhalb von ungefähr zwei Stunden 22,5 Teile 30%ige Natriumhydroxydlösung zu und rührt sie so lange, bis die Kupplung beendigt ist. Die ausgeschiedene Monoazoverbindung wird ab- filtriert, mit verdünnter Natriumchloridlö- sung gewaschen und getrocknet. Sie ist ein schwarzes Pulver, das sich in Wasser mit violetter und in konzentrierter Schwefelsäure mit roter Farbe löst.
Zur Überführung in die Metallkomplex verbindung werden 10,5 Teile der so gewon nenen Monoazoverbindung in 550 Teilen. Wasser und 5 Teilen Türkischrotöl suspen diert. Man versetzt die Suspension bei 95-98 mit einer konzentrierten, mittels Am moniak neutralisierten wässerigen Lösung aus 5,8 Teilen kristallisiertem Natrium- bichromat und erhitzt sie zum Sieden.
Hier auf wird die Masse während vier Stunden ge kocht, dann setzt man ihr 7,5 Teile 30%ige Natriumhydroxydlösung zu und stellt ihren % -Wert durch Zusatz von. Essigsäure auf 9-10. Nach weiterem zweistündigem Sieden filtriert man die heisse Lösung und fällt die gebildete Chromkomplexverbindung aus dem Filtrat durch Zusatz von Natriumchlorid bei <B>95'</B> aus.
Der abgeschiedene Farbstoff wird abgenutscht und im Vakuum getrocknet. Er ist in Wasser mit grauer Farbe gut löslich und färbt Wolle und synthetische Polyamidfasern aus neutralem Bad in licht- und walkechten grauen Tönen.
Process for the preparation of a chromium-containing azo dye. The subject of the present patent is a process for the production of a chromium-containing azo dye, which consists in that 1 mol of the diazo compound from 1-oxy-2-aminobenzene-4-sulfonic acid methylamide with 1 mol of 1-carbo-n-propoxyamino - 7-oxynaphthahn couples and treated the monoazo compound obtained with a chromium-releasing agent.
The process leads to a dye which contains less than 2 atoms of chromium for every 2 molecules of monoazo compound. One therefore uses less than 2 atoms of chromium per 2 molecules of monoazo compound for metallizing the monoazo compound according to the invention.
In the following example, the 'files mean parts by weight and the percentages mean percentages by weight.
<I> Example: </I> 20 parts of 1-oxy-2-aminobenzene-4-sulfonic acid methylamide are dissolved in a mixture of 22 parts of concentrated hydrochloric acid and 220 parts of water and dissolved at 0-2 'by adding a concentrated aqueous solution of <B> 6.9 </B> parts of sodium nitrite diazotized. The diazo suspension formed is poured into a solution, cooled to 0-2, of 24 parts of 1-carbon-n-propoxyamino-7-oxynaphthalene, 14 parts of 30% sodium hydroxide solution,
20 parts of sodium carbonate and 670 parts of water are run in. 22.5 parts of 30% sodium hydroxide solution are then added to the coupling compound at 0-2 within about two hours and the mixture is stirred until the coupling is complete. The precipitated monoazo compound is filtered off, washed with dilute sodium chloride solution and dried. It is a black powder that dissolves in water with purple color and in concentrated sulfuric acid with red color.
To convert the compound into the metal complex, 10.5 parts of the monoazo compound thus won are in 550 parts. Suspended water and 5 parts of Turkish red oil. A concentrated aqueous solution of 5.8 parts of crystallized sodium bichromate, neutralized with ammonia, is added to the suspension at 95-98, and it is heated to the boil.
Here the mass is boiled for four hours, then 7.5 parts of 30% sodium hydroxide solution are added to it and its% value is established by adding. Acetic acid to 9-10. After a further two hours of boiling, the hot solution is filtered and the chromium complex compound formed is precipitated from the filtrate by adding sodium chloride at 95 '.
The deposited dye is filtered off with suction and dried in vacuo. It is readily soluble in water with a gray color and dyes wool and synthetic polyamide fibers from a neutral bath in lightfast and milled gray tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH302155T | 1952-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302155A true CH302155A (en) | 1954-10-15 |
Family
ID=4491277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302155D CH302155A (en) | 1952-03-06 | 1952-03-06 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302155A (en) |
-
1952
- 1952-03-06 CH CH302155D patent/CH302155A/en unknown
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