CH198149A - Process for the production of a vat dye of the dipyrazole anthrone series. - Google Patents
Process for the production of a vat dye of the dipyrazole anthrone series.Info
- Publication number
- CH198149A CH198149A CH198149DA CH198149A CH 198149 A CH198149 A CH 198149A CH 198149D A CH198149D A CH 198149DA CH 198149 A CH198149 A CH 198149A
- Authority
- CH
- Switzerland
- Prior art keywords
- dipyrazole
- production
- anthrone
- series
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- XIVYZXBSCPPEDQ-UHFFFAOYSA-N 10h-anthracen-9-one;1h-pyrazole Chemical class C=1C=NNC=1.C=1C=NNC=1.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 XIVYZXBSCPPEDQ-UHFFFAOYSA-N 0.000 title description 5
- 239000000975 dye Substances 0.000 claims description 7
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012021 ethylating agents Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GLFVDTDXXORFKP-UHFFFAOYSA-N cyclohexanol;sodium Chemical compound [Na].OC1CCCCC1 GLFVDTDXXORFKP-UHFFFAOYSA-N 0.000 description 1
- -1 diethyl dipyrazole anthrone Chemical compound 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines IKilpenfarbstofès der Dipyrazolanthronreihe. In der deutschen Patentschrift Nr. 302259 ist ein Verfahren zur Herstellung von stickstoff haltigen Küpenfarbstoffen der Anthracenreihe beschrieben, das darin besteht, dass man in das Dipyrazolanthron stufenweise zwei ver schiedene Alkylreste einführt.
Es wurde nun gefunden, dass man besonders wertvolle, gelbstichig rote Farbstoffe der Di- pyrazolanthronreihe erhält, wenn man in das Molekül des Dipyrazolanthrons zunächst einen Cycloalkylrest und hierauf in das so erhal tene Zwischenprodukt eine Alkylgruppe ein führt.
Die neuen Farbstoffe zeichnen sich ausser durch Gelbstich der damit erhaltenen Fär bungen durch leichte Löslichkeit der Leuko- verbindung und gute Echtheitseigenschaften aus; sie haben weiter den Vorteil, beim Seifen weit weniger umzuschlagen als das Diäthyl- dipyrazolanthron.
Vorliegendes Patent -bezieht sich nun auf ein Verfahren zur Herstellung eines Küpen- farbstoffes der Dipyrazolantbronreibe, dadurch gekennzeichnet, dass man Dipyrazolanthron zunächst mit einem Mol eines cyclohegylieren- denMittels und das gebildete Zwischenprodukt mit einem Mol eines äthylierenden Mittels behandelt.
Der so erhaltene neue Farbstoff derFormel
EMI0001.0028
ist ein dunkelrotes Pulver, das sich in kon zentrierter Schwefelsäure mit orangeroter Farbe löst und Baumwolle aus blauer Küpe in lebhaft roten Tönen färbt.
<I>Beispiel:</I> 530 Teile (97 o/oiges) Dipyrazolarrthr-ori- kalium werden mit 69 Teilen waRserfreiem Kaliumkarbonat, etwa 5000 Teilen o-Dichlor- benzol und 620 Teilen Berrzolsulfosärirecyclo- hexylester (dargestellt durch Umsetzung von Cyclohexanolnatrium mit Benzolsulfochlorid) unter Rühren 8-10 Stunden auf 120-125 o C erhitzt.
Das Reaktionsprodukt wird heiss ab gesaugt, das anhaftende Lösungsmittel durch Destillation mit Wasserdampf entfernt und das Umsetzungsprodukt mit Wasser ausge kocht. Das so erhaltene Zwischenprodukt, ein orangegelbes Pulver, wird mit 850 Teilen Ätzalkali versetzt, bis zur Bildung des Kali umsalzes längere Zeit vermahlen und im Va kuum bei<B>70</B> getrocknet.
640 Teile des so erhaltenen N-Cyclohexyl- dipyrazolanthronkaliums werden mit o-Di- chlorbenzol zu einer gleichmässigen Paste angerührt, mit 530 Teilen p-Toluolsrrlfosäure- äthylester versetzt und einige Zeit auf 120 bis <B>125'</B> erhitzt. Der gebildete Farbstoff wird heiss abgesaugt, mit heissem o-Dichlor#benzol gewaschen, durch Auskochen mit Wasser ge reinigt und getrocknet.
Process for the preparation of an I-pen dye of the dipyrazole anthrone series. German Patent No. 302259 describes a process for the preparation of nitrogen-containing vat dyes of the anthracene series, which consists in introducing two different alkyl radicals into the dipyrazole anthrone in stages.
It has now been found that particularly valuable, yellowish red dyes of the dipyrazole anthrone series are obtained if a cycloalkyl radical is first introduced into the molecule of the dipyrazole anthrone and then an alkyl group is introduced into the intermediate product thus obtained.
The new dyes are distinguished not only by the yellow tinge of the dyeings obtained therewith, but also by the easy solubility of the leuco compound and good fastness properties; they also have the advantage of being far less active than diethyl dipyrazole anthrone when soaping.
The present patent now relates to a process for the production of a vat dye of dipyrazolantbrone grater, characterized in that dipyrazolanthrone is first treated with one mole of a cyclohegylating agent and the intermediate product formed with one mole of an ethylating agent.
The new dye of the formula thus obtained
EMI0001.0028
is a dark red powder that dissolves in concentrated sulfuric acid with an orange-red color and dyes cotton from a blue vat in vivid red tones.
<I> Example: </I> 530 parts (97%) of Dipyrazolarrthr-ori- potassium are mixed with 69 parts of anhydrous potassium carbonate, about 5000 parts of o-dichlorobenzene and 620 parts of Berrzenesulfosärirecyclohexylester (prepared by reaction of cyclohexanol sodium with Benzene sulfochloride) heated to 120-125 o C for 8-10 hours with stirring.
The reaction product is sucked off hot, the adhering solvent is removed by distillation with steam and the reaction product is boiled out with water. The intermediate product thus obtained, an orange-yellow powder, is mixed with 850 parts of caustic alkali, ground for a long time until the potassium salt is formed and dried in a vacuum at <B> 70 </B>.
640 parts of the N-cyclohexyldipyrazole anthrone potassium thus obtained are mixed with o-dichlorobenzene to form a uniform paste, mixed with 530 parts of ethyl p-toluenesrlfoate and heated to 120 to 125 'for a while. The dye formed is filtered off with suction while hot, washed with hot o-dichloro benzene, purified by boiling with water and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE198149X | 1936-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH198149A true CH198149A (en) | 1938-06-15 |
Family
ID=5756803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH198149D CH198149A (en) | 1936-06-09 | 1937-05-28 | Process for the production of a vat dye of the dipyrazole anthrone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH198149A (en) |
-
1937
- 1937-05-28 CH CH198149D patent/CH198149A/en unknown
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