CH160950A - Process for the preparation of a water-soluble red dye of the anthraquinone series. - Google Patents
Process for the preparation of a water-soluble red dye of the anthraquinone series.Info
- Publication number
- CH160950A CH160950A CH160950DA CH160950A CH 160950 A CH160950 A CH 160950A CH 160950D A CH160950D A CH 160950DA CH 160950 A CH160950 A CH 160950A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- red
- dye
- preparation
- anthraquinone series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000001044 red dye Substances 0.000 title claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 6
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- YDUGVOUXNSWQSW-UHFFFAOYSA-N 3-bromo-1h-pyridin-2-one Chemical compound OC1=NC=CC=C1Br YDUGVOUXNSWQSW-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 carbethoxy-2-methyl-4-chloranthrapyridone Chemical compound 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 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
- 238000001035 drying Methods 0.000 description 1
- HVHSIRSBSHIZGM-UHFFFAOYSA-N ethyl 4-bromo-2-methyl-1-oxonaphtho[2,3-f]quinoline-3-carboxylate Chemical compound C1=CC=C2C=C3C(C(=O)C(C)=C(N4Br)C(=O)OCC)=C4C=CC3=CC2=C1 HVHSIRSBSHIZGM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines wasserlöslichen roten Farbstoffes der Anthrachinonreihe. Das vorliegende Verfahren betrifft die Darstellung eines roten Farbstoffes der Anthra- chinonreihe und ist dadurch gekennzeichnet, dass man Car-bäthoxy - 2 - methyl - 4 - halogen- anthrapyridon mit p-Chloranilin kondensiert, die erhaltene Base mit schwachem Oleum behandelt und die Monosulfosäure aus dem Reaktionsgemisch isoliert.
<I>Beispiel 1:</I> 40 Teile Carbäthoxy - 2 - methyl - 4 - brom- anthrapyridon, 40 Teile p-Chloranilin, 16 Teile Kaliumacetat und 2 Teile Kupferoxyd werden unter gutem Rühren auf 150-160 erhitzt, bis im Bodensatz einer Probe in Benzol unter dem Mikroskop kein Brompyridon mehr zu sehen ist. Man verdünnt nun mit etwas Nitrobenzol, dann mit Alkohol und gewinnt das Kondensationsprodukt durch Absaugen, Waschen und Trocknen.
Die so erhaltene Base wird durch Sul- fieren mit schwachem Oleum bei 40-50 in einen wasserlöslichen Farbstoff übergeführt. Der Farbstoff stellt in trockenem Zu stande ein dunkelrotes Pulver dar; er löst sich blaurot in Wasser und blaustichig rot in Schwefelsäure. Die Schwefelsäurelösung wird beim Erwärmen mit Borsäure violett. Der Farbstoff färbt Wolle und Seide in echten blaustichig roten Tönen von grosser Leb haftigkeit an.
<I>Beispiel 2:</I> 40 Teile p-Chloranilin, 10 Teile Carb- äthoxy-2-methyl-4-chloranthrapyridon, 3,5 Teile Naliumacetat und 0,05 Teile Kupfer sulfat werden wie im Beispiel 1 bis zur Bil dung der Base erhitzt. Die aus dem Kon densationsgemisch isolierte Base ist mit der jenigen des Beispiels 1 identisch und wird in gleicher Weise in den sauren Farbstoff übergeführt.
Process for the preparation of a water-soluble red dye of the anthraquinone series. The present process relates to the preparation of a red dye of the anthrachinone series and is characterized in that car-ethoxy-2-methyl-4-halo-anthrapyridone is condensed with p-chloroaniline, the base obtained is treated with weak oleum and the monosulfonic acid is removed isolated from the reaction mixture.
<I> Example 1: </I> 40 parts of carbethoxy - 2 - methyl - 4 - bromo anthrapyridone, 40 parts of p-chloroaniline, 16 parts of potassium acetate and 2 parts of copper oxide are heated to 150-160 with thorough stirring until the sediment is in place no bromopyridone can be seen under the microscope in a sample in benzene. It is now diluted with a little nitrobenzene and then with alcohol, and the condensation product is obtained by filtering off with suction, washing and drying.
The base obtained in this way is converted into a water-soluble dye by sulphuring with weak oleum at 40-50. When dry, the dye is a dark red powder; it dissolves bluish red in water and bluish red in sulfuric acid. The sulfuric acid solution turns purple when heated with boric acid. The dye stains wool and silk in real blue-tinged red tones that are extremely vivid.
<I> Example 2: </I> 40 parts of p-chloroaniline, 10 parts of carbethoxy-2-methyl-4-chloranthrapyridone, 3.5 parts of sodium acetate and 0.05 part of copper sulfate are as in Example 1 up to bil heating of the base. The base isolated from the condensation mixture is identical to that of Example 1 and is converted into the acidic dye in the same way.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE160950X | 1931-04-29 | ||
| DE50631X | 1931-06-05 | ||
| CH156452T | 1931-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH160950A true CH160950A (en) | 1933-03-31 |
Family
ID=27177377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH160950D CH160950A (en) | 1931-04-29 | 1932-04-21 | Process for the preparation of a water-soluble red dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH160950A (en) |
-
1932
- 1932-04-21 CH CH160950D patent/CH160950A/en unknown
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