CH169937A - Process for the preparation of an oxynaphthetriazole. - Google Patents
Process for the preparation of an oxynaphthetriazole.Info
- Publication number
- CH169937A CH169937A CH169937DA CH169937A CH 169937 A CH169937 A CH 169937A CH 169937D A CH169937D A CH 169937DA CH 169937 A CH169937 A CH 169937A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- sulfonic acid
- preparation
- oxynaphthetriazole
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- SSQQBRZUIXIPIP-UHFFFAOYSA-N 5-diazo-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 SSQQBRZUIXIPIP-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000431 copper oxide 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
- 238000001914 filtration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Oxynaphttriazols. Gemäss dem im Hauptpatent beschrie benen Verfahren erhält inan ein Oxynaplit- triazol, wenn inan den aus 4-Nitro-l-diazo- benzol durch saure Kupplung mit 1-Amino- 8-oxytiaphtaliti-3.6-disulfosäure erhältlichen o-Aminoazofarbstoff mit Verbindungen des zweiwertigen Kupfers oxydiert,
bezw. mit andern Oxydationsmitteln in Gegenwart von zweiwertigen Kupferverbindungen behandelt.
Wie nun weiter gefunden wurde, erhält man ein ähnliches, für die gleichen Zwecke brauchbares Oxynaphttriazol, wenn man den Farbstoff, wie er aus diazotierter 4-Nitro-l- aininobenzol-2-stilfosätire durch Kuppeln mit 2-Amino-8-oxynaphtalin-6-sulfosäure in saurer Lösung erhältlich ist, mit Verbindungen des zweiwertigen Kupfers behandelt.
Die Oxydation kann in neutraler, alka lischer, amnioniakalkalischer oder saurer Lö sung durchgeführt werden. Andere Oxyda tionsmittel, die für sich allein nicht zum Ziel führen, beispielsweise Wasserstoffsuperoxyd, Natriumhypochlorit, können in Gegenwart von zur Triazolbildung unzureichenden Men gen Kupferverbindung für den genannten Zweck Verwendung finden.
Das erhaltene, bisher nicht bekannte Oxy- naphttriazol bildet ein wertvolles Zwischen produkt für die Herstellung von Farbstoffen. <I>Beispiel:</I> Der durch saure Kupplung aus 21,8 Tei len 4-Niti-o-l-aniinobenzol-2-sulfosäure und 23,9 Teilen 2-Amino-8-oxynapthalin-6-sulfo- säure erhaltene Farbstoff wird nach Neutra lisieren mit Natriumkarbonat bei<B>800</B> mit einer wässerigen Lösung von 55 Teilen kristallisiertem Kupfersulfat, die mit Am moniak übersättigt ist, versetzt und so lange erhitzt,
bis die ursprünglich blaue Farbe völlig in gelbbraun umgeschlagen ist. Dann wird das Ammoniak durch Kochen ausge trieben, der Farbstoff vom Kupferoxdul durch Filtration getrennt und in üblicher Weise ausgesalzen. Das erhaltene Oxynaphttriazol stellt ein gelbbraunes Pulver dar und bildet mit Diazoverbindungen Farbstoffe.
Process for the preparation of an oxynaphthotriazole. According to the process described in the main patent, an oxynaplittriazole is obtained if inan the o-aminoazo dye obtainable from 4-nitro-1-diazo-benzene by acidic coupling with 1-amino-8-oxytiaphthalite-3,6-disulfonic acid with compounds of the divalent Copper oxidized,
respectively treated with other oxidizing agents in the presence of divalent copper compounds.
As has now been found further, a similar oxynaphthotriazole, which can be used for the same purposes, is obtained if the dye is obtained from diazotized 4-nitro-1-aininobenzene-2-stilfosätire by coupling with 2-amino-8-oxynaphthalene-6 -sulfonic acid is available in acidic solution, treated with compounds of divalent copper.
The oxidation can be carried out in neutral, alkaline, amniotic alkaline or acidic solution. Other oxidizing agents that do not achieve the goal on their own, for example hydrogen peroxide, sodium hypochlorite, can be used in the presence of insufficient amounts of triazole formation copper compound for the stated purpose.
The previously unknown oxynaphthotriazole obtained forms a valuable intermediate for the production of dyes. <I> Example: </I> The dye obtained by acid coupling from 21.8 parts of 4-niti-ol-aniinobenzene-2-sulfonic acid and 23.9 parts of 2-amino-8-oxynapthalene-6-sulfonic acid After neutralization with sodium carbonate at <B> 800 </B>, an aqueous solution of 55 parts of crystallized copper sulphate, which is supersaturated with ammonia, is added and heated until
until the originally blue color has turned completely yellow-brown. Then the ammonia is expelled by boiling, the dye is separated from the copper oxide by filtration and salted out in the usual way. The oxynaphttriazole obtained is a yellow-brown powder and forms dyes with diazo compounds.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169937X | 1932-04-20 | ||
| CH164836T | 1932-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169937A true CH169937A (en) | 1934-06-15 |
Family
ID=25718044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169937D CH169937A (en) | 1932-04-20 | 1932-09-24 | Process for the preparation of an oxynaphthetriazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169937A (en) |
-
1932
- 1932-09-24 CH CH169937D patent/CH169937A/en unknown
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