CH157565A - Process for the preparation of a vat dye of the anthraquinone series. - Google Patents
Process for the preparation of a vat dye of the anthraquinone series.Info
- Publication number
- CH157565A CH157565A CH157565DA CH157565A CH 157565 A CH157565 A CH 157565A CH 157565D A CH157565D A CH 157565DA CH 157565 A CH157565 A CH 157565A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- anthraquinone series
- vat dye
- dye
- anthraquinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat 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
- 239000000975 dye Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 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 2
- 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 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-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
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 description 1
- YRTZPHPTXYXTIB-UHFFFAOYSA-N 5-chloro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1Cl YRTZPHPTXYXTIB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Küpenfarbstoffes der Anthrachinonreihe. Im Hauptpatent ist ein Verfahren zur Darstellung eines güpenfarbstoffes beschrie ben, bei dem 2.1-(N)-Anthrachinonakridon- 6-karbonsäurechlorid mit 1-Amino-4-methoxy- anthrachinon durch Erhitzen in einem Lö sungsmittel umgesetzt wird.
Es wurde nun gefunden, dass man in ganz analoger Weise einen Küpenfarbstoff von ähnlichen wertvollen Eigenschaften er halten kann, wenn man 2.1-(S)-Anthra- chinontbioxanthon-6-karbonsäurechlorid von der Formel
EMI0001.0013
mit 1-Amino-4-benzoylaminoanthrachinon durch Erhitzen in einem Lösungsmittel kon densiert.
<I>Beispiel:</I> 1,9 Teile 2. 1-(S)-Anthrachinonthioxanthorr- 6-karbonsäureehlorid der oben angegebenen Formel, erhältlich zum Beispiel aus 1-Chlor- anthrachinon-6-karbonsäure durch Konden- sation mit Thiosalicylsärrre, Ringschluss mit Schwefelsäure und Behandeln der erhaltenen garbonsäure mit Phosphorpentachlorid, wer den in 100 Teilen Nitrobenzol mit 1,7 Teilen 1-Amino-4-benzoylaminoanthracbinon so lange auf 170-180 C erhitzt, bis die Farbstoff bildung beendet ist.
Der beim Erkalten aus geschiedene Farbstoff wird noch durch Aus kochen mit Trichlorbenzol gereinigt. Er färbt die Baumwollfaser aus blauer Küpe in rot orangen Tönen.
Process for the preparation of a vat dye of the anthraquinone series. In the main patent, a process for the preparation of a quality dye is described in which 2.1- (N) -anthraquinone acridone-6-carboxylic acid chloride is reacted with 1-amino-4-methoxy-anthraquinone by heating in a solvent.
It has now been found that you can keep a vat dye of similar valuable properties in a completely analogous manner, if you 2.1- (S) -Anthra- quinontbioxanthone-6-carboxylic acid chloride of the formula
EMI0001.0013
condensed with 1-amino-4-benzoylaminoanthraquinone by heating in a solvent.
<I> Example: </I> 1.9 parts of 2. 1- (S) -anthraquinone thioxanthore- 6-carboxylic acid chloride of the formula given above, obtainable, for example, from 1-chloro-anthraquinone-6-carboxylic acid by condensation with thiosalicylic acid , Ring closure with sulfuric acid and treating the obtained carboxylic acid with phosphorus pentachloride, who heated in 100 parts of nitrobenzene with 1.7 parts of 1-amino-4-benzoylaminoanthracbinone at 170-180 C until the dye formation is complete.
The dye that separates out on cooling is cleaned by boiling off with trichlorobenzene. He dyes the cotton fiber from the blue vat in red-orange tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE157565X | 1930-01-18 | ||
| CH153488T | 1930-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH157565A true CH157565A (en) | 1932-09-30 |
Family
ID=25716213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH157565D CH157565A (en) | 1930-01-18 | 1930-12-19 | Process for the preparation of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH157565A (en) |
-
1930
- 1930-12-19 CH CH157565D patent/CH157565A/en unknown
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