AT45602B - Process for the preparation of dyes of the gallocyanin series. - Google Patents
Process for the preparation of dyes of the gallocyanin series.Info
- Publication number
- AT45602B AT45602B AT45602DA AT45602B AT 45602 B AT45602 B AT 45602B AT 45602D A AT45602D A AT 45602DA AT 45602 B AT45602 B AT 45602B
- Authority
- AT
- Austria
- Prior art keywords
- dyes
- series
- preparation
- gallocyanin
- nitroso compounds
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- YBGOLOJQJWLUQP-UHFFFAOYSA-N gallocyanin Chemical class OC(=O)C1=CC(=O)C(O)=C2OC3=CC(N(C)C)=CC=C3N=C21 YBGOLOJQJWLUQP-UHFFFAOYSA-N 0.000 title 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 12
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 229940074391 gallic acid Drugs 0.000 claims description 6
- 235000004515 gallic acid Nutrition 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- ADAUKUOAOMLVSN-UHFFFAOYSA-N gallocyanin Chemical class [Cl-].OC(=O)C1=CC(O)=C(O)C2=[O+]C3=CC(N(C)C)=CC=C3N=C21 ADAUKUOAOMLVSN-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UCMYJOPIPDLTRT-UHFFFAOYSA-N n,n-diethyl-2-nitrosoaniline Chemical compound CCN(CC)C1=CC=CC=C1N=O UCMYJOPIPDLTRT-UHFFFAOYSA-N 0.000 description 4
- HLVGXGQCLASQJU-UHFFFAOYSA-N 3,4,5-trihydroxy-n-phenylbenzamide Chemical compound OC1=C(O)C(O)=CC(C(=O)NC=2C=CC=CC=2)=C1 HLVGXGQCLASQJU-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- -1 gallic acid ester Chemical class 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
- AQSOTOUQTVJNMY-UHFFFAOYSA-N 7-(dimethylamino)-4-hydroxy-3-oxophenoxazin-10-ium-1-carboxylic acid;chloride Chemical class [Cl-].OC(=O)C1=CC(=O)C(O)=C2OC3=CC(N(C)C)=CC=C3[NH+]=C21 AQSOTOUQTVJNMY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LGDPTPLJZGPOJL-UHFFFAOYSA-N n,n-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-UHFFFAOYSA-N 0.000 description 1
- MWHUIOFIRPAVBJ-UHFFFAOYSA-N n-methyl-n-(2-methylphenyl)nitrous amide Chemical compound O=NN(C)C1=CC=CC=C1C MWHUIOFIRPAVBJ-UHFFFAOYSA-N 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Farbstoffen der Gallocyaninreihe.
Es wurde gefunden, dass die bekannte Kondensation von Gallussäure und ihren Derivaten, wie z. B. Gallaminsäure, Gallussäureester, Gallanilid usw. mit den Nitrosoverbindungen aromatischer Amine wesentlich glatter verläuft, wenn man die Salzsäure in den bisher ausschliesslich verwandten salzsauren Nitrosoverbindungen durch solche Säuren ersetzt, die mit den Nitrosokörpern der Amine oder den sich bildenden Farbstoffen (zweckmässig mit beiden) schwer lösliche Salze bilden. Solche Säuren sind z. B. Überschwefelsäure, RhodanwasserstoNsäure, 1. 5- und 2. 6-Naphtalindisulfosäure. Die Salze dieser Säuren mit den gebräuchlichsten Nitrosoverbindungen sekundärer und tertiärer Amine wie z. B.
Nitrosodimethylanilin, Nitrosodiäthylanilin, Nitrosomonomethyl-o-toluidin, Nitrosomonomethyl-und -monoäthylanilin, Nitrosodimethyl- und -diäthyl-m-chloranili usw. bilden fast durchweg prismenförmig Kristalle von gelblicher Farbe.
Der grosse Vorteil des Verfahrens zeigt sich besonders deutlich in den Fällen, in denen nach den bisherigen Verfahren nur Spuren eines Farbstoffes entstehen, z. B. bei der Darstellung des Farbstoffes aus Nitrosodiäthylanilin und Gallussäure, der hier in guter Ausbeute erhalten wird.
Beispiel l.
10 Teile Gallussäure werden in 200 Teilen Methylalkohol gelöst, zu der siedenden Lösung allmählich 20 Teile 1.5-naphtalindisulfosaures Nitrosodiäthylanilin zugegeben und so lange erhitzt, bis die Nitrosoverbindung verschwunden ist. Dann wird abgesaugt, gewaschen und getrocknet und eventuell in das salzsaure Salz überführt.
Beispiel 2.
5 Teile Gallanilid werden in 100 Teilen Methylalkohol gelöst und zu der siedenden Lösung allmählich 7 Teile rhodanwasserstoffsaures Nitrosodiäthylanilin zugegeben. Nach
Verschwinden der Nitrosoverbindung lässt man erkalten und saugt den ausgeschiedenen Farbstoff ab, der zum Färben und Drucken zweckmässig in seine Snlfosäure übergeführt wird.
An Stelle der in den Beispielen angeführten Gallussäure oder ihres Anilids können äquivalente Mengen anderer Gallussäurederivate und an Stelle der angegebenen Nitrososalze die äquivalenten Mengen geeigneter Salze anderer Nitrosoverbindungen verwendet werden.
Man geht zweckmässig von den entsprechenden schwer löslichen Salzen der Nitroso- verbindungen aus, doch steht nichts im Wege die Bildung derselben erst in der Konden- sationslösung vorzunehmen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of dyes of the gallocyanin series.
It has been found that the known condensation of gallic acid and its derivatives, such as. B. gallamic acid, gallic acid ester, gallanilide etc. with the nitroso compounds of aromatic amines runs much smoother if the hydrochloric acid in the previously exclusively used hydrochloric acid nitroso compounds is replaced by acids that are associated with the nitroso bodies of the amines or the dyes formed (suitably with both) Form poorly soluble salts. Such acids are e.g. B. supersulphuric acid, rhodanic acid, 1. 5- and 2. 6-naphthalene disulfonic acid. The salts of these acids with the most common nitroso compounds of secondary and tertiary amines such. B.
Nitrosodimethylaniline, nitrosodiethylaniline, nitrosomonomethyl-o-toluidine, nitrosomonomethyl- and monoethylaniline, nitrosodimethyl- and diethyl-m-chloranili etc. almost all form prismatic crystals of yellowish color.
The great advantage of the method is particularly evident in cases in which only traces of a dye are produced according to previous methods, e.g. B. in the representation of the dye from nitrosodiethylaniline and gallic acid, which is obtained here in good yield.
Example l.
10 parts of gallic acid are dissolved in 200 parts of methyl alcohol, 20 parts of 1,5-naphtalindisulfosaures nitrosodiethylaniline are gradually added to the boiling solution and the mixture is heated until the nitroso compound has disappeared. It is then filtered off with suction, washed and dried and possibly converted into the hydrochloric acid salt.
Example 2.
5 parts of gallanilide are dissolved in 100 parts of methyl alcohol and 7 parts of nitrosodiethylaniline with rhodanic acid are gradually added to the boiling solution. After
Disappearance of the nitroso compound is allowed to cool and the precipitated dye is suctioned off, which is expediently converted into its sulfonic acid for dyeing and printing.
Instead of the gallic acid or its anilide listed in the examples, equivalent amounts of other gallic acid derivatives can be used and, instead of the specified nitroso salts, the equivalent amounts of suitable salts of other nitroso compounds can be used.
One expediently starts from the corresponding sparingly soluble salts of the nitroso compounds, but nothing stands in the way of their formation in the condensation solution.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE45602X | 1909-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT45602B true AT45602B (en) | 1911-01-10 |
Family
ID=5625049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT45602D AT45602B (en) | 1909-01-30 | 1909-12-22 | Process for the preparation of dyes of the gallocyanin series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT45602B (en) |
-
1909
- 1909-12-22 AT AT45602D patent/AT45602B/en active
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