CH293919A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH293919A CH293919A CH293919DA CH293919A CH 293919 A CH293919 A CH 293919A CH 293919D A CH293919D A CH 293919DA CH 293919 A CH293919 A CH 293919A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- acid
- production
- vat
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 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 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 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
- 239000002253 acid Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/44—Dyes with acylated amino groups the acyl groups being residues of a heterocyclic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 252533. Verfahren zur Herstellung eines Küpenfarbstoffes. 1's wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man l.-(Pyridin-3'-carboyla.mino)-4-amino-6- eblor-anthrachinon mit einem funktionellen Derivat der in 4-Stellung durch eine Sulfo- morpholidgruppe substituierten Benzol-l-car- bonsäure umsetzt.
Der neue Farbstoff löst sich in konz. Schwefelsäure mit roter Farbe und färbt Baumwolle aus olivgrüner Küpe in echten blaustichigen Rosatönen.
Als funktionelles Derivat der genannten Carbonsäure 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 Mono-, Di- oder Triehlorbenzol, vorgenommen werden, wobei vorteilhaft bei erhöhter Temperatur gearbeitet wird.
<I>Beispiel:</I> 27 Teile Benzoesäure - p - sulfomorpholid werden in 250 Teilen trockenem Nitrobenzol verteilt und nach Zufügen von 15 Teilen Thionylchlorid und einer geringen Menge Py-. ridin anderthalb Stunden bei<B>11.0</B> bis 120 verrührt. Hierauf wird mit 37 Teilen 1-(Py ridin-3'-carboylamino)-1-amino-6-ehlor-anthra- chinon versetzt und zwei Stunden bei 120 bis 130 weitergerührt. Beim Erkalten fällt der Farbstoff als rotes, fein kristallines Pulver aus, welches abgesauä , gut mit kochendem Alkohol gewaschen und getrocknet wird.
<B> Additional patent </B> to main patent no. 252533. Process for the production of a vat dye. 1's it has been found that a valuable vat dye can be produced if l .- (pyridine-3'-carboyla.mino) -4-amino-6-eblor-anthraquinone with a functional derivative of the 4-position by a sulfo- Morpholide substituted benzene-1-carboxylic acid converts.
The new dye dissolves in conc. Sulfuric acid with red color and dyes cotton from an olive-green vat in real blue-tinged pink tones.
An acid halide, for example the acid chloride, can advantageously be used as the functional derivative of the carboxylic acid mentioned. The reaction can be carried out, for example, in an inert solvent, preferably of a relatively high boiling point, such as mono-, di- or trihlobenzene, advantageously at elevated temperature.
<I> Example: </I> 27 parts of benzoic acid - p - sulfomorpholide are distributed in 250 parts of dry nitrobenzene and, after adding 15 parts of thionyl chloride and a small amount of Py-. Stirred for an hour and a half at <B> 11.0 </B> to 120. 37 parts of 1- (pyridine-3'-carboylamino) -1-amino-6-chloro-anthraquinone are then added and the mixture is stirred at 120 to 130 for a further two hours. On cooling, the dye precipitates as a red, finely crystalline powder, which is drained, washed well with boiling alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH252533T | 1944-08-03 | ||
| CH293919T | 1946-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH293919A true CH293919A (en) | 1953-10-15 |
Family
ID=25729679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH293919D CH293919A (en) | 1944-08-03 | 1946-11-18 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH293919A (en) |
-
1946
- 1946-11-18 CH CH293919D patent/CH293919A/en unknown
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