CH146777A - Process for the preparation of an etch-resistant dye of the gallocyanin series. - Google Patents
Process for the preparation of an etch-resistant dye of the gallocyanin series.Info
- Publication number
- CH146777A CH146777A CH146777DA CH146777A CH 146777 A CH146777 A CH 146777A CH 146777D A CH146777D A CH 146777DA CH 146777 A CH146777 A CH 146777A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- color
- printing
- new
- gallocyanin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 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 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 4
- RBQIPEJXQPQFJX-UHFFFAOYSA-N 3,4,5-trihydroxybenzamide Chemical compound NC(=O)C1=CC(O)=C(O)C(O)=C1 RBQIPEJXQPQFJX-UHFFFAOYSA-N 0.000 claims description 4
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- LVWRXVYDWDCORS-UHFFFAOYSA-N N,N,3-trimethyl-2-nitrosoaniline Chemical compound N(=O)C1=C(N(C)C)C=CC=C1C LVWRXVYDWDCORS-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 claims 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 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 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines ätzbeständigen Farbstoffes der Gallocyaninreilie. Das Hauptpatent bezieht sich auf ein Verfahren zur Herstellung eines neuen Farb stoffes der Gallocyaninreihe, welches dadurch gekennzeichnet ist, dass der aus Gallamid und Nitrosodiäthyl-meta-toluidin erhältliche Farbstoff unter gleichzeitiger Einwirkung von oxydierenden Mitteln mit Diäthyl-par-a-pileny- lendiamin kondensiert wird.
Der neue Farbstoff entspricht wahrschein lich folgender Formel:
EMI0001.0011
An der mit x bezeichneten Stelle - in Metastellung zur Diäthylaminogruppe - trägt er einen Substituenten (CHs). Verglichen mit dem entsprechenden bekannten Farbstoff, der an der bezeichneten Stelle keinen Sub- stituenten trägt, erweist sich der neue meta- substituierte Farbstoff als viel widerstands fähiger gegenüber Reduktionsmitteln. Er ist deshalb besonders geeignet für die Verwen dung im Beduktionsbuntätzdruck.
Es wurde nun gefunden, dass ein ähnli cher, ebenfalls ätzbeständiger Gallocyanin- farbstoff erhalten wird, wenn im Verfahren des Hauptpatentes an Stelle des genannten Farbstoffes der entsprechende aus Gallamid und Nitrosodimethyl-meta-toluidiri verwendet und dieser unter gleichzeitiger Einwirkung von oxydierenden Mitteln mit Diäthyl-para- phenylendiamin kondensiert wird.
Das Verfahren wird erläutert durch fol gendes Beispiel: 35 Teile des Farbstoffes aus Gallamid und Nitrosodimethyl-meta-toluidin werden mit 100 Teilen Diäthyl-para-phenylendiamin und 10 Teilen Dinitrobenzol während 3 Stunden auf 70 C erhitzt. plan setzt hernach unter Umrühren 300 Teile Alkohol zu, lässt voll ständig erkalten und filtriert, presst und trock net. Man erhält das Kondensationsprodukt in Form eines grünlichen kristallinischen Pulvers.- Dasselbe löst sich in konzentrierter Schwe felsäure mit roter Farbe, die beim Verdünnen mit Wasser rotviolett wird.
Als Chlorhydrat löst sich der neue Körper mit blauer Farbe, die auf Zusatz von überschüssiger Salzsäure rotviolett wird. Aus dieser Lösung kann die Farbbase mit Natriumacetatlösung in Form von blauen Flocken gefällt werden.
Der Farbstoff wird zum Färben und Drucken vorteilhaft in Form seiner Leuko- verbindung verwendet. Im Chromdruck liefert er marineblaue Töne, die rotstichiger sind als diejenigen des Produktes des Hauptpa tentes. Dank seiner Beständigkeit gegen Reduktionsmittel eignet er sich für die Ver wendung im Reduktions-Buntätzdruck.
Das Verfahren kann auch so ausgeführt werden, dass entsprechend der Arbeitsweise des schweizerischen Patentes Nr.<B>70867</B> der im Beispiel genannte Ausgangsfarbstoff mit dem Diaminöl bei gewöhnlicher Temperatur viele Stunden lang durchgerührt wird, wobei an Stelle des Dinitrobenzols der Sauerstoff der Luft die Rückoxydation der in der Re- aktionsmasse auftretenden Leukoverbindung des Ausgangsfarbstoffes besorgt.
Process for the preparation of an etch-resistant dye of the Gallocyaninreilie. The main patent relates to a process for the production of a new dye of the gallocyanin series, which is characterized in that the dye obtainable from gallamide and nitrosodiethyl meta-toluidine condenses with diethyl par-a-pilenylenediamine under the simultaneous action of oxidizing agents becomes.
The new dye will likely match the following formula:
EMI0001.0011
At the point marked x - in the meta position to the diethylamino group - it bears a substituent (CHs). Compared with the corresponding known dye which has no substituent at the point indicated, the new meta-substituted dye proves to be much more resistant to reducing agents. It is therefore particularly suitable for use in low-pressure etching printing.
It has now been found that a similar, also etch-resistant gallocyanine dye is obtained if the corresponding one of gallamide and nitrosodimethyl-meta-toluidiri is used in the process of the main patent in place of the dye mentioned and this under the simultaneous action of oxidizing agents with diethyl Paraphenylenediamine is condensed.
The process is illustrated by the following example: 35 parts of the dye from gallamide and nitrosodimethyl-meta-toluidine are heated to 70 ° C. for 3 hours with 100 parts of diethyl-para-phenylenediamine and 10 parts of dinitrobenzene. plan then adds 300 parts of alcohol while stirring, lets it cool down completely and then filters, presses and dries. The condensation product is obtained in the form of a greenish crystalline powder. The same dissolves in concentrated sulfuric acid with a red color, which turns red-violet when diluted with water.
As a hydrochloric acid, the new body dissolves with a blue color, which turns red-violet when excess hydrochloric acid is added. The color base can be precipitated from this solution with sodium acetate solution in the form of blue flakes.
The dye is advantageously used for dyeing and printing in the form of its leuco compound. In chrome printing, it delivers navy blue tones that are more reddish than those of the product of the main patent. Thanks to its resistance to reducing agents, it is suitable for use in reduction color etching printing.
The process can also be carried out in such a way that, in accordance with the procedure of Swiss Patent No. 70867, the starting dye mentioned in the example is stirred with the diamine oil at ordinary temperature for many hours, with the oxygen in place of the dinitrobenzene Air is responsible for the reoxidation of the leuco compound of the starting dye which occurs in the reaction mass.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE146777X | 1927-11-26 | ||
| CH143714T | 1928-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146777A true CH146777A (en) | 1931-04-30 |
Family
ID=25714345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146777D CH146777A (en) | 1927-11-26 | 1928-11-22 | Process for the preparation of an etch-resistant dye of the gallocyanin series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146777A (en) |
-
1928
- 1928-11-22 CH CH146777D patent/CH146777A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH143714A (en) | Process for the preparation of an etch-resistant dye of the gallocyanin series. | |
| CH146776A (en) | Process for the preparation of an etch-resistant dye of the gallocyanin series. | |
| AT55688B (en) | Process for the preparation of stain-coloring oxazine dyes. | |
| AT71647B (en) | Process for the preparation of derivatives of 2,3-oxynaphthoic acid amide. | |
| AT46291B (en) | Process for the preparation of red basic dyes. | |
| CH148997A (en) | Process for the production of an etch-resistant dye of the gallocyanin series. | |
| DE696332C (en) | Process for the production of black sulfur dyes | |
| CH225501A (en) | Process for the production of an etch-resistant stain dye. | |
| CH148996A (en) | Process for the production of an etch-resistant dye of the gallocyanin series. | |
| CH143715A (en) | Process for the preparation of an etch-resistant dye of the gallocyanin series. | |
| CH143713A (en) | Process for the preparation of an etch-resistant dye of the gallocyanin series. | |
| CH146864A (en) | Process for the preparation of an etch-resistant dye of the gallocyanin series. | |
| CH148995A (en) | Process for the production of an etch-resistant dye of the gallocyanin series. | |
| CH153202A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH359229A (en) | Process for the preparation of iron nitroso-B-naphthol dyes | |
| CH216590A (en) | Process for the preparation of a nitrogen-containing condensation product of fluoranthene. | |
| CH216591A (en) | Process for the preparation of a nitrogen-containing condensation product of fluoranthene. | |
| CH232890A (en) | Process for the preparation of a new dye of the dioxazine series. | |
| CH216586A (en) | Process for the preparation of a nitrogen-containing condensation product of fluoranthene. | |
| CH198893A (en) | Process for the production of a sulfur dye. | |
| CH146190A (en) | Process for the preparation of an etch-resistant gallocyanine derivative. | |
| CH103142A (en) | Process for the production of a new indigoid dye. | |
| CH100188A (en) | Process for the preparation of an acridine dye. | |
| CH190329A (en) | Process for the preparation of a condensation product of the anthraquinone series. | |
| CH122278A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. |