CH293886A - 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
- CH293886A CH293886A CH293886DA CH293886A CH 293886 A CH293886 A CH 293886A CH 293886D A CH293886D A CH 293886DA CH 293886 A CH293886 A CH 293886A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- copper
- coupling
- dye
- polyazo dye
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 9
- 229910052802 copper Inorganic materials 0.000 title claims description 9
- 239000010949 copper Substances 0.000 title claims description 9
- 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 11
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 4
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-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
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 claims description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 230000001335 demethylating effect Effects 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- HGPNYHCCQHOKAS-UHFFFAOYSA-N NC1=C(C2=C(C=CC=C2C=C1)S(=O)(=O)O)S(=O)(=O)O Chemical compound NC1=C(C2=C(C=CC=C2C=C1)S(=O)(=O)O)S(=O)(=O)O HGPNYHCCQHOKAS-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
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- Coloring (AREA)
Description
Verfahren zur Herstellung eines kupferhaltigen Polyazofarbstoffes. Gregenstand des vorliegenden Patentes ist. ein Verfahren zur Herstellung eines kupfer haltigen Polyazofarbstoffes, welches darin be steht, dass man die durch Kuppeln von diano tierter 2-Aminonaphthalin-4,8-disulfonsäure mit -lAmino-3-methylbenzol, Weiterdiazotie- ren der Monoazoverbindung und Kuppeln mit 1-Amino ?-,5-dimethoxybenzol erhältliche Aminodisazoverbindung dianotiert,
den Diazo- körper mit dem Kupferkomplex aus der durch saure Kupplung von dianotierter 1-Amino-4- nitrobenzol-2-carbonsäure mit 2-Amino-5-oxy- naphthalin-7-sulfonsäure und anschliessenden Austausch der Aminogruppe gegen die Hy- droxylgruppe erhältlichen Monoazoverbindung vereinigt und den so gewonnenen Polyazofarb- stoff entmethylierend kupfert.
<I>Beispiel:</I> 56,7 Teile der Aminodisazoverbindung, welche man durch Kuppeln von dianotierter 2-Aminonaphthalin-l,8-disulfonsäure mit 1- Amino-3-methylbenzol, Weiterdiazotieren und Kuppeln mit. 1-Amino-2,5-dimethoxybenzol erhält, werden mit 7 Teilen Natriumnitrit un ter Zusatz von 50 Teilen konzentrierter Salz säure dianotiert.
Die erhaltene Diazoverbin- dung vereinigt man bei Zimmertemperatur mit der Lösung aus 49,4 Teilen der kupfer haltigen Monoazoverbindung, welche man durch saure Kupplung von dianotierter 1- Amino - 4 - nitrobenzol - 2 - earbonsäure mit 2- Amiiio - 5 - oxynaphthalin - 7-sulfonsäure,
an schliessendem Austausch der Aminogruppe gegen die Hy droxylgruppe und nachfolgendes Kupfern erhält, 600 Teilen Wasser und 1500 Teilen Pyridin. Man rührt die Masse noch <B>'</B>Stunden lang bei 50 bis 60 , worauf die Kupplung beendigt ist.
Die erhaltene Farbstofflösung wird nun auf 90 erwärmt. Man 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 bei 90 bis 95 . Nach Ablauf dieser Zeit hat sich die Kupferkomplexverbindung unter Aufspal tung der Methoxygruppe vollständig gebildet; sie wird durch Zusatz von Essigsäure zur Metallisierungslösung abgeschieden, abgesaugt und hierauf in 1000 Teilen Wasser angerührt.
Nach der Überführung ins Natriumsalz wird sie durch Zusatz von Natriumchlorid zur Farbstofflösung ausgefällt, filtriert und schliesslich bei 90 getrocknet.
Der neue kupferhaltige Polyazofarbstoff ist ein dunkles Pulver und färbt Baumwolle und Fasern aus regenerierter Cellulose in grünstiehig grauen Tönen von hervorragender Lichtechtheit und sehr guten Nassechtheiten.
Process for the production of a copper-containing polyazo dye. The subject matter of the present patent is. a process for the preparation of a copper-containing polyazo dye, which consists in the fact that by coupling diano-tated 2-aminonaphthalene-4,8-disulfonic acid with -l-amino-3-methylbenzene, further diazotizing the monoazo compound and coupling with 1-amino ? -, 5-dimethoxybenzene available aminodisazo compound dianotized,
the diazo body with the copper complex obtained from the acidic coupling of dianotated 1-amino-4-nitrobenzene-2-carboxylic acid with 2-amino-5-oxynaphthalene-7-sulfonic acid and subsequent exchange of the amino group for the hydroxyl group The monoazo compound is combined and the polyazo dye thus obtained is demethylated copper.
<I> Example: </I> 56.7 parts of the aminodisazo compound, which is obtained by coupling dianotated 2-aminonaphthalene-1,8-disulfonic acid with 1-amino-3-methylbenzene, further diazotizing and coupling with. 1-Amino-2,5-dimethoxybenzene is obtained, dianotized with 7 parts of sodium nitrite under the addition of 50 parts of concentrated hydrochloric acid.
The diazo compound obtained is combined at room temperature with the solution of 49.4 parts of the copper-containing monoazo compound, which is obtained by acidic coupling of dianotated 1-amino-4-nitrobenzene-2-carboxylic acid with 2-amino-5-oxynaphthalene-7 sulfonic acid,
on subsequent exchange of the amino group by the hydroxyl group and subsequent copper, 600 parts of water and 1500 parts of pyridine are obtained. The mass is stirred for a further <B> '</B> hours at 50 to 60 hours, after which the coupling is complete.
The dye solution obtained is then heated to 90 °. To copperize the tetrakisazo dye, 25 parts of crystallized copper sulfate, dissolved in 100 parts of water and 25 parts of concentrated ammonia, are added, and it is stirred at 90 to 95 for 8 to 10 hours. After this time, the copper complex compound has formed completely with splitting of the methoxy group; it is deposited by adding acetic acid to the metallizing solution, filtered off with suction and then mixed with 1000 parts of water.
After being converted into the sodium salt, it is precipitated by adding sodium chloride to the dye solution, filtered and finally dried at 90 °.
The new copper-containing polyazo dye is a dark powder and dyes cotton and fibers from regenerated cellulose in greenish gray shades of excellent lightfastness and very good wetfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH293886T | 1951-02-14 | ||
| CH290585T | 1953-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH293886A true CH293886A (en) | 1953-10-15 |
Family
ID=25733034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH293886D CH293886A (en) | 1951-02-14 | 1951-02-14 | Process for the production of a copper-containing polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH293886A (en) |
-
1951
- 1951-02-14 CH CH293886D patent/CH293886A/en unknown
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