CH293890A - Process for the production of a copper-containing polyazo dye. - Google Patents
Process for the production of a copper-containing polyazo dye.Info
- Publication number
- CH293890A CH293890A CH293890DA CH293890A CH 293890 A CH293890 A CH 293890A CH 293890D A CH293890D A CH 293890DA CH 293890 A CH293890 A CH 293890A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- amino
- sulfonic acid
- diazotized
- polyazo dye
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 10
- 229910052802 copper Inorganic materials 0.000 title claims description 10
- 239000010949 copper Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 claims description 2
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000004699 copper complex Chemical class 0.000 claims description 2
- 230000001335 demethylating effect Effects 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring 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
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 290585. Verfahren zur Herstellung eines kupferhaltigen Polyazofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines kupfer haltigen Polyazofarbstoffes, welches darin be steht, dass man die durch Kuppeln von diano tierter 1 Aminonaphthalin-5-sulfonsäure mit 1- Aminonaphthalin - 7 - sulfonsäure, Weiter d.iazotieren der Monoazoverbindung und Kup peln mit 1 Amino-2-methoxy-5-methylbenzol erhältliche Disazoverbindung dianotiert, den Diazokörper mit,
dem Kupferkomplex aus der durch saure Kupplung von dianotiertem 1- Amino-2-m.ethoxy benzol - 5 -sulfonsäure mit 2- Amino-5-oxynaphthalin-7-sttlfonsäure und an schliessenden Austausch der Aminogruppe gegen die Oxy gruppe erhältlichen Monoa.zo- verbindung vereinigt und den so gewonnenen Polyazofarbstoff entmethylierend kupfert. <I>Beispiel:
</I> 61,9 Teile der Aminodisazoverbindung, welche man durch Kuppeln von dianotierter 1-Aniinonaphthalin-5-sulfonsäure mit 1-Amino- naphthalin-7-sttlfonsäure, Weiterdiazotieren und Kuppeln mit 1 Amino-2-methoxy-5-me- thylbenzol in Gegenwart von Natriumbiearbo- nat erhält, werden mit 7 Teilen Natriumnitrit unter Zusatz von 50 Teilen konzentrierter Salzsäure dianotiert.
Die erhaltene Diazov er- bindung vereinigt man bei Zimmertemperatur mit der Lösung aus 50,1 Teilen der kupfer haltigen hlonoazoverbindung, welche man durch saure Kupplung von dianotierter 1- Amino-2-methoxybenzol-5-sulfonsäure mit 2- Amino-5-oxynaphthalin-7-sulfonsäure, an- schliessenden Austausch der Aminogruppe gegen die Hydroxylgruppe und nachfolgendes Kupfern erhält, 600 Teilen Wasser und 1500 Teilen Pyridin. Man rührt die Masse noch 2 Stunden lang bei 50 bis 60 ,
worauf die Kupplung beendigt ist.
Die erhaltene Parbstofflösung wird nun auf 90 erwärmt, plan setzt ihr zur Kupferung des Tetrakisazofarbstoffes 25 Teile kristalli siertes Kupfersulfat, gelöst in 100 Teilen Was ser und 25 Teilen konzentriertem Ammoniak, zu und rührt sie während 8 bis 10 Stunden hei 90 bis 95 . Naeh Ablauf dieser Zeit hat sich die Kupferkomplexverbindung unter Aufspal tung der Methoxygruppe vollständig gebildet; sie wird durch Zusatz von Essigsäure zur Me- tallisierungslösung abgeschieden, abgesaugt und hierauf in 1000 Teilen Wasser angerührt..
Nach der Überführung ins Natriumsalz wird sie durch Zusatz von Natriumchlorid zur Parbstofflösung ausgefällt, filtriert und schliesslich bei 90 getrocknet.
Der neue kupferhaltige Polyazofarbstoff ist ein dunkles Pulver und färbt Baumwolle und Fasern aus regenerierter Cellulose in grauen Tönen von hervorragender Lichtecht heit und sehr guten Nassechtheiten.
Additional patent to main patent No. 290585. Process for the production of a copper-containing polyazo dye. The subject of the present patent is a process for the preparation of a copper-containing polyazo dye, which is be that by coupling diano-tated 1 aminonaphthalene-5-sulfonic acid with 1-aminonaphthalene-7-sulfonic acid, further d.iazotize the monoazo compound and Kup peln with 1 amino-2-methoxy-5-methylbenzene available disazo compound dianotized, the diazo body with,
the copper complex from the mono-amino group obtained by acidic coupling of dianotated 1-amino-2-methoxy benzene-5-sulfonic acid with 2-amino-5-oxynaphthalene-7-sulfonic acid and subsequent replacement of the amino group by the oxy group Compound combined and the thus obtained polyazo dye demethylating copper. <I> example:
</I> 61.9 parts of the aminodisazo compound, which is obtained by coupling dianotated 1-aniinonaphthalene-5-sulfonic acid with 1-amino-naphthalene-7-sttlfonic acid, further diazotizing and coupling with 1 amino-2-methoxy-5-me- ethylbenzene obtained in the presence of sodium bicarbonate are dianotized with 7 parts of sodium nitrite with the addition of 50 parts of concentrated hydrochloric acid.
The Diazov compound obtained is combined at room temperature with the solution of 50.1 parts of the copper-containing hlonoazo compound, which is obtained by acidic coupling of dianotated 1-amino-2-methoxybenzene-5-sulfonic acid with 2-amino-5-oxynaphthalene- 7-sulfonic acid, subsequent exchange of the amino group for the hydroxyl group and subsequent copper obtained, 600 parts of water and 1500 parts of pyridine. The mass is stirred for a further 2 hours at 50 to 60,
whereupon the clutch is terminated.
The paraffin solution obtained is now heated to 90, and it is used to copperize the tetrakisazo dye 25 parts of crystallized copper sulfate, dissolved in 100 parts of water and 25 parts of concentrated ammonia, and stir it for 8 to 10 hours at 90 to 95. After this time has elapsed, the copper complex compound has formed completely with splitting of the methoxy group; it is separated out by adding acetic acid to the metallizing solution, filtered off with suction and then mixed with 1000 parts of water.
After it has been converted into the sodium salt, it is precipitated by adding sodium chloride to the paraffin solution, filtered and finally dried at 90 °.
The new copper-containing polyazo dye is a dark powder and dyes cotton and fibers made from regenerated cellulose in gray shades of excellent lightfastness and very good wet fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH293890T | 1951-02-14 | ||
| CH290585T | 1953-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH293890A true CH293890A (en) | 1953-10-15 |
Family
ID=25733038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH293890D CH293890A (en) | 1951-02-14 | 1951-02-14 | Process for the production of a copper-containing polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH293890A (en) |
-
1951
- 1951-02-14 CH CH293890D patent/CH293890A/en unknown
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