CH242510A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH242510A CH242510A CH242510DA CH242510A CH 242510 A CH242510 A CH 242510A CH 242510D A CH242510D A CH 242510DA CH 242510 A CH242510 A CH 242510A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- vat dye
- acid
- dye
- benzoylaminoanthraquinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 4
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxo-1-anthracenyl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WXPWTKPQXYLOJH-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)sulfonylbenzene Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=CC=C(OC)C=C1 WXPWTKPQXYLOJH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1-Amino-4-benzoylaminoanthra- chinon mit Mitteln behandelt, die imstande sind, den Rest
EMI0001.0006
einzuführen. Der neue Farbstoff bildet rote Xristalle vom Schmelzpunkt 320-323 , die sich in konzentrierter Schwefelsäure mit roter Farbe lösen, und färbt Baumwolle aus der Küpe in echten roten Tönen.
Als Mittel, die imstande sind, den Rest
EMI0001.0011
einzuführen, sind die 4-(p-Methoxyphenyl- sülfon)-1-carbonsäure sowie ihre funktionel len Derivate zu erwähnen. Besonders zweck mässig ist die Verwendung der entsprechen den Säurehalogenide, insbesondere des Säure chlorids. Die Umsetzung erfolgt zweckmässig in hochsiedenden Lösungsmitteln, wie Nitro- benzol oder ortho-Dichlorbenzol, bei erhöhter Temperatur.
<I>Beispiel:</I> 14,6 Teile 4-(p-Methoxyphenylsülfon)-1- carbonsäure werden in. 320 Teilen waeser- freiem o-Dichlorbenzol verteilt, und die Mi schung wird nach Zufügen von 40 Teilen Thionylöhlorid und einer, geringen Menge Pyridin zuerst eine Stunde bei 80-90 , dann eine weitere Stunde bei 100-110 unter Rühren gehalten.
Hierauf destilliert man das überschüssige Thionylchlorid und etwas o-Di- chlorbenzol ab und ermässigt die Temperatur auf 100 , gibt 17,25 Teile 1-Amino-4-benzoyl- aminoanthrachinon hinzu und rührt 2 Stun den bei 170-175 , schliesslich i/4 Stunde bei Siedetemperatur.
Nach dem Erkalten wird das ausgeschiedene 1-(4'-[4"-Methoxyphenyl- sulfon] - benzaylamino) - 4 - benzoylamino - anthrachinon abfiltriert, mit Alkohol aus gewaschen und getrocknet.
Process for the production of a vat dye. It has been found that a valuable vat dye can be made by treating 1-amino-4-benzoylaminoanthraquinone with agents that are able to do the rest
EMI0001.0006
to introduce. The new dye forms red crystals with a melting point of 320-323, which dissolve in concentrated sulfuric acid with a red color, and dyes cotton from the vat in real red tones.
As means that are able to do the rest
EMI0001.0011
to be introduced, the 4- (p-methoxyphenyl sulphon) -1-carboxylic acid and its functional derivatives should be mentioned. The use of the corresponding acid halides, in particular the acid chloride, is particularly useful. The reaction is expediently carried out in high-boiling solvents, such as nitrobenzene or ortho-dichlorobenzene, at an elevated temperature.
<I> Example: </I> 14.6 parts of 4- (p-methoxyphenylsulfone) -1-carboxylic acid are distributed in 320 parts of anhydrous o-dichlorobenzene, and the mixture is after adding 40 parts of thionyl chloride and one , small amount of pyridine first kept at 80-90 for one hour, then at 100-110 for another hour with stirring.
The excess thionyl chloride and some o-dichlorobenzene are then distilled off and the temperature is reduced to 100, 17.25 parts of 1-amino-4-benzoylaminoanthraquinone are added and the mixture is stirred for 2 hours at 170-175, finally 1/4 Hour at boiling temperature.
After cooling, the precipitated 1- (4 '- [4 "-Methoxyphenylsulfon] - benzaylamino) - 4 - benzoylamino - anthraquinone is filtered off, washed with alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242510T | 1943-11-01 | ||
| CH239953T | 1943-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH242510A true CH242510A (en) | 1946-05-15 |
Family
ID=25728465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH242510D CH242510A (en) | 1943-11-01 | 1943-11-01 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH242510A (en) |
-
1943
- 1943-11-01 CH CH242510D patent/CH242510A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH242510A (en) | Process for the production of a vat dye. | |
| CH242509A (en) | Process for the production of a vat dye. | |
| CH239953A (en) | Process for the production of a vat dye. | |
| CH242511A (en) | Process for the production of a vat dye. | |
| DE846592C (en) | Process for the production of Kuepen dyes | |
| DE696424C (en) | Process for the preparation of anthraquinone dyes | |
| DE507561C (en) | Process for the preparation of valuable Kuepen dyes of the anthraquinone acridone series | |
| DE393268C (en) | Process for the representation of gray Kuepen colors | |
| CH239007A (en) | Process for the production of a new anthraquinone dye. | |
| CH267316A (en) | Process for the production of a vat dye. | |
| CH279834A (en) | Process for the production of a vat dye. | |
| CH188225A (en) | Process for the production of a vat dye of the anthraquinone series. | |
| CH259729A (en) | Process for the production of a vat dye. | |
| CH252533A (en) | Process for the production of a vat dye. | |
| CH292691A (en) | Process for the production of a vat dye. | |
| CH274710A (en) | Process for the production of a vat dye. | |
| CH247604A (en) | Process for the production of a vat dye. | |
| CH247605A (en) | Process for the production of a vat dye. | |
| CH274438A (en) | Process for the production of a vat dye. | |
| CH370511A (en) | Process for the preparation of dyes of the anthraquinone series | |
| CH266028A (en) | Process for the production of a vat dye. | |
| CH272571A (en) | Process for the production of a vat dye. | |
| CH173744A (en) | Process for the production of a vat dye. | |
| CH243843A (en) | Process for the production of a vat dye. | |
| CH274713A (en) | Process for the production of a vat dye. |