CH252533A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH252533A CH252533A CH252533DA CH252533A CH 252533 A CH252533 A CH 252533A CH 252533D A CH252533D A CH 252533DA CH 252533 A CH252533 A CH 252533A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- carboxylic acid
- production
- process according
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000002253 acid Substances 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
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000012442 inert solvent 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 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 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 einem funktionellen Derivat 8er in 4-Stellung durch eine N-Dimethyl@sulfami,d- gruppe substituierten Benzol-l-.carbonsäure umsetzt.
Der neue Farbstoff bildet rote Kristalle, die sich in konzentrierter Schwefelsäure mit roter Farbe lösen und Baumwolle aus blau- violetter Küpe in sehr echten, nach.dem Ab seifen leuchtenden Rosatönen färben.
Ale funktionelles Derivat der genannten Carbonsä-ure kann mit Vorteil ein Säurehalo genid, beispielsweise das Säurechlorid, ver wendet werden. Die Umsetzung kann bei spielsweise in einem indifferenten Lösungs mittel, vorzugsweise von relativ hohem Siede punkt, wie Nitrobenzol, Mono-, Di- oder Tri- chlorbenzol, vorgenommen werden, wobei vor teilhaft bei erhöhter Temperatur gearbeitet wird.
Das für das vorliegende Verfahren benö tigte Benzol-l-carbo.nsäure-4-(N-dimethyl)- sulfamid lässt sich z. B. wie folgt herstellen: 44 Teile Benzoesäure-4-sülfochlorid wer den mit ?,10 Teilen wässeriger Dimethylamin- lösung von 16,% und<B>150</B> Teilen Wasser 21@ Stunden verrührt, wobei die Temperatur auf 315 steigt.
Nun wird mit 1.0,%iger Salz säure angesäuert und,die ausgefallene Säure abgenutseht, mit Wasser ausgewaschen und getrocknet.
<I>Beispiel:</I> 3,45 Teile Benzol-l=earbonsäure-4-(N-@di- methyl)-sulfamid werden in<B>IN</B> Teilen was serfreiem o-Dichlorbenzol verteilt und die Misühung wird nach Zufügen von 13, Teilen Thionylchforid und einer geringen Menge Pyridin zuerst eine halbe Stunde bei 80-90'", dann eine Viertelstunde bei 100--110 unter Rühren gehalten.
Hierauf destilliert man das überschüssige Thionylchiorid und etwas o-Di- ehlorbenzol vorteilhaft im Vakuum ab und gibt bei 100 5,15 Teile 1-Amino-4-benzoyl- aminoanthrachinon hinzu, rührt 2 Stunden bei l.70=175 , schliesslich eine Viertelstunde bei Siedetemperatur. Naeh dem Erkalten wird das ausgeschiedene 1-(4'-N-Dimethyl- sn'lfamidbenzoylamino)
- 4- benzoyl-aminoan.- thrachinon abfiltriert, mit Alkohol ausge waschen und getrocknet.
Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1-amino-4-benzoylaminoanthra- .quinone with a functional derivative 8er in the 4-position by an N-dimethyl @ sulfami, d- group substituted benzene-1-. carboxylic acid converts.
The new dye forms red crystals which dissolve in concentrated sulfuric acid with a red color and turn cotton from a blue-violet vat in very real, bright pink shades after soaping.
Any functional derivative of the carboxylic acid mentioned can advantageously be an acid halide, for example the acid chloride. The reaction can be carried out, for example, in an inert solvent, preferably of a relatively high boiling point, such as nitrobenzene, mono-, di- or trichlorobenzene, being carried out at elevated temperature before geous.
The benzene-l-carbo.nsäure-4- (N-dimethyl) - sulfamide required for the present process can be z. B. prepare as follows: 44 parts of benzoic acid 4-sulphonyl chloride are stirred with 10 parts of aqueous dimethylamine solution of 16.% and 150 parts of water for 21 hours, the temperature rising to 315 hours .
It is now acidified with 1.0% hydrochloric acid and, the acid which has precipitated out, washed out with water and dried.
<I> Example: </I> 3.45 parts of benzene-l = carboxylic acid-4- (N- @ dimethyl) -sulfamide are distributed in parts of water-free o-dichlorobenzene and the After adding 13 parts of thionyl chloride and a small amount of pyridine, the mixture is kept stirring for half an hour at 80-90 '", then for a quarter of an hour at 100-110.
The excess thionyl chloride and some o-dichlorobenzene are then distilled off, advantageously in vacuo, and 5.15 parts of 1-amino-4-benzoylaminoanthraquinone are added at 100, the mixture is stirred at 1.70 = 175 for 2 hours, and finally for a quarter of an hour Boiling temperature. After cooling, the precipitated 1- (4'-N-dimethyl-sn'lfamidbenzoylamino)
- 4-benzoyl-aminoan.- thrachinone filtered off, washed out with alcohol and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH252533T | 1944-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH252533A true CH252533A (en) | 1948-01-15 |
Family
ID=4469475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH252533D CH252533A (en) | 1944-08-03 | 1944-08-03 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH252533A (en) |
-
1944
- 1944-08-03 CH CH252533D patent/CH252533A/en unknown
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