AT72815B - Process for the preparation of green-blue dyes of the gallocyanin series and leuco derivatives thereof. - Google Patents
Process for the preparation of green-blue dyes of the gallocyanin series and leuco derivatives thereof.Info
- Publication number
- AT72815B AT72815B AT72815DA AT72815B AT 72815 B AT72815 B AT 72815B AT 72815D A AT72815D A AT 72815DA AT 72815 B AT72815 B AT 72815B
- Authority
- AT
- Austria
- Prior art keywords
- green
- series
- gallocyanin
- blue dyes
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000001045 blue dye Substances 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 description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 150000004984 aromatic diamines Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ADAUKUOAOMLVSN-UHFFFAOYSA-N gallocyanin Chemical compound [Cl-].OC(=O)C1=CC(O)=C(O)C2=[O+]C3=CC(N(C)C)=CC=C3N=C21 ADAUKUOAOMLVSN-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Verfahren zur Darstellung grünblauer Farbstoffe der Gallocyaninreihe und von Leuko- derivaten derselben.
In der Stammpatentschrift Nr. 34778 sind Kondensationsprodukte der Gallocyaninfarbstoffe beschrieben, welche dadurch erhalten werden, dass aromatische, mindestens eine freie Amidogruppe enthaltende Diamine mit Gallocyaninen erhitzt werden. Zur Verhinderung der gleichzeitig sich vollziehenden Bildung von Leukogallocyaninen wird in einer Anzahl der angeführten Beispiele dem Reaktionsgemenge Dinitrobenzol zugesetzt.
Wie in der Patentschrift Nr. 34778 dann des weiteren ausgeführt wird, werden die Kondensationsprodukte in ihre Leukoverbindungen übergeführt.
Es wurde nun gefunden, dass man zu denselben Kondensationsprodukten, wie sie in der Stammpatentschrift Nr. 34778 beschrieben wurden, auch gelangen kann, wenn eine Mischung eines Gallocyanins mit einem Diamin bei gewöhnlicher Temperatur längere Zeit durchgerührt wird. Der Vorteil dreser Arbettweise besteht in erster Linie darin, dass es für die Kondensatronsprodukte aus Diammen und den Gallocyaninen aus Gallussäure er-
EMI1.1
Beispiel !.
Zu einer Auflösung von 130 ky Amidodimethylauilin in 200 1 Alkoho ! wird eine Mischung von 100 k/Gallocyanin (dargestellt aus Gallussäure und Nitrosodimethylanilin) und 200 1 Alkohol zugegeben und die Mischung während 24 Stunden durchgerührt. Nun wird abgenutscht und das Reaktionsprodukt von noch anbaftendem Diamin durch Ausrühren mit schwacher Salzsäure befreit. Mit dem Diamin geht das Kondensationsprodukt zum grössten Teil in Losung, durch Zusatz von Kochsalz wird es wieder ausgefällt. Das
EMI1.2
wässeriger Natriumkarbonatlösung löslich. Endlich wird es zur Überführung in sein Leuko- derivat reduziert.
Beispiel H.
EMI1.3
Amidodimethylanilin eingerührt und während 60 Stunden bei gewöhnlicher Temperatur damit durchgerührt, d. h. solange, bis eine Probe der Mischung nach Entfernung des Diamins in wässeriger Natriumkarbonatlösung unlöslich geworden ist. Ist dies erreicht, so wird das Reaktionsprodukt mit Alkohol verdünnt und durch Abnutschon von den Mutterlaugen getrennt. Hierauf wird mit schwacher Salzsäure durchgerührt, abfiltriert, gepresst und reduziert.
<Desc/Clms Page number 2>
BeispielIII.
100 kir des aus Gallussäuremethylestor und Nitrosodhnethylanilin dargestellten Gallocyanins werden in 500 kg Amidodimethylanilin eingetragen und bei gewöhnlicher Temperatur in einem emaillierten Gefäss während 48 Stunden energisch durchgerührt. Hierauf wird das Reaktionsprodukt mit 100 l kaltem Alkohol verdünnt, auf der Nutsche von den Mutterlaugen getrennt und schliesslich gepresst Die Presskuchen werden dann zerkleinert und zur völligen Entfernung noch anhaftenden Diamins mit verdünnter Salzsäure durchgerührt. Das Reaktionsprodukt wird schliesslich abfiltricrt und durch Reduktion in sein Leukoderivat übergeführt.
<Desc / Clms Page number 1>
Process for the preparation of green-blue dyes of the gallocyanin series and of leuco derivatives thereof.
The parent patent specification No. 34778 describes condensation products of gallocyanine dyes, which are obtained by heating aromatic diamines containing at least one free amido group with gallocyanines. To prevent the simultaneous formation of leukogallocyanines, dinitrobenzene is added to the reaction mixture in a number of the examples given.
As is then further explained in patent specification No. 34778, the condensation products are converted into their leuco compounds.
It has now been found that the same condensation products as described in the parent patent specification No. 34778 can also be obtained if a mixture of a gallocyanine with a diamine is stirred for a long time at ordinary temperature. The advantage of this method is primarily that it is necessary for the condensate products from diamonds and the gallocyanines from gallic acid.
EMI1.1
Example!.
To dissolve 130 ky of amidodimethylailine in 200 l of alcohol! a mixture of 100 k / gallocyanin (prepared from gallic acid and nitrosodimethylaniline) and 200 l of alcohol is added and the mixture is stirred for 24 hours. It is then suction filtered and the reaction product is freed from any diamine still adhering by stirring with weak hydrochloric acid. Most of the condensation product goes into solution with the diamine, and it is precipitated again by adding sodium chloride. The
EMI1.2
soluble in aqueous sodium carbonate solution. It is finally reduced to be converted into its leuco derivative.
Example H.
EMI1.3
Amidodimethylaniline stirred in and stirred with it for 60 hours at ordinary temperature, d. H. until a sample of the mixture has become insoluble in aqueous sodium carbonate solution after the diamine has been removed. Once this has been achieved, the reaction product is diluted with alcohol and separated from the mother liquors by suction. It is then stirred with weak hydrochloric acid, filtered off, pressed and reduced.
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Example III.
100 kir of the gallocyanine prepared from gallic acid methyl ester and nitrosodine ethyl aniline are introduced into 500 kg amidodimethyl aniline and vigorously stirred in an enamelled vessel at normal temperature for 48 hours. The reaction product is then diluted with 100 l of cold alcohol, separated from the mother liquors on the suction filter and finally pressed. The press cakes are then crushed and stirred with dilute hydrochloric acid to completely remove any diamine that is still adhering. The reaction product is finally filtered off and converted into its leuco derivative by reduction.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT72815D AT72815B (en) | 1906-10-06 | 1914-11-13 | Process for the preparation of green-blue dyes of the gallocyanin series and leuco derivatives thereof. |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT34778T | 1906-10-06 | ||
| DE72815X | 1913-11-14 | ||
| AT72815D AT72815B (en) | 1906-10-06 | 1914-11-13 | Process for the preparation of green-blue dyes of the gallocyanin series and leuco derivatives thereof. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT72815B true AT72815B (en) | 1916-12-11 |
Family
ID=27149451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT72815D AT72815B (en) | 1906-10-06 | 1914-11-13 | Process for the preparation of green-blue dyes of the gallocyanin series and leuco derivatives thereof. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT72815B (en) |
-
1914
- 1914-11-13 AT AT72815D patent/AT72815B/en active
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