CH257946A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH257946A CH257946A CH257946DA CH257946A CH 257946 A CH257946 A CH 257946A CH 257946D A CH257946D A CH 257946DA CH 257946 A CH257946 A CH 257946A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- acid
- production
- vat dye
- red
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 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
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives 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
- 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
- 238000003756 stirring Methods 0.000 description 3
- RFSGXAYVLVRDND-UHFFFAOYSA-N 1-benzoylpiperidine-4-sulfonic acid Chemical compound C1CC(S(=O)(=O)O)CCN1C(=O)C1=CC=CC=C1 RFSGXAYVLVRDND-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye 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
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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-ben.zoylaminoanthra- chinon mit einem funktionellen Derivat der in 4-Stellung durch eine Sulfopiperidid- gruppe substituierten Benzol-l-carbonsäure umsetzt.
Der neue Farbstoff kristallisiert in roten Nadeln, welche sich in konz. Schwefelsäure mit roter Farbe lösen, .und färbt Baumwolle aus braunvioletter $üpe in blaustichig roten Tönen.
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 Siedepunkt, wie Mono-, Di- oder Trichlor- benzol, vorgenommen werden, wobei vorteil haft bei erhöhter Temperatur gearbeitet wird.
Das für das vorliegende Verfahren be nötigte Benzol-l-carbonsäure-4-sulfopiperidid lässt sich zum Beispiel durch Umsetzen von Benzoesäure-4-sulfochlorid mit einer wässeri gen Lösung von Piperidin herstellen.
Beispiel: 102,8 Teile Benzol-l-carbonsäure-4-sulfo- piperidid werden in 2000 Teilen wasserfreiem o-Dichlorbenzol verteilt, und nach Zufügen von 150 Teilen Thionylchlorid und einer ge ringen Menge Pyridin wird die Temperatur unter Rühren langsam auf 100 gesteigert.
Nachdem die Temperatur eine Stunde unter Rühren bei 100 belassen wurde, destilliert man das überschüssige Thionylchlorid und etwas o-Dichlorbenzol im Vakuum ab, gibt 136,8 Teile 1-Amino-4-benzoylaminoanthra- chinon hinzu und steigert die Temperatur ganz langsam unter Rühren auf 170 biss 175 . Endlich erhitzt. man noch 10 Minuten zum Sieden und lässt erkalten.
Der in sehr guter Ausbeute ausfallende Farbstoff wird abfil- triert und mit heissem Alkohol und Äther gewaschen.
Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1-amino-4-benzoylaminoanthraquinone is reacted with a functional derivative of the benzene-1-carboxylic acid substituted in the 4-position by a sulfopiperidide group.
The new dye crystallizes in red needles, which are in conc. Dissolve sulfuric acid with red dye, and dyes cotton from brown-violet oil in bluish red tones.
When. Functional derivative of the carboxylic acid mentioned, an acid halide, for example the acid chloride, can be used with advantage. The reaction can be carried out, for example, in an inert solvent, preferably of a relatively high boiling point, such as mono-, di- or trichlorobenzene, it being advantageous to operate at elevated temperature.
The benzene-1-carboxylic acid-4-sulfopiperidide required for the present process can be prepared, for example, by reacting benzoic acid-4-sulfochloride with an aqueous solution of piperidine.
Example: 102.8 parts of benzene-1-carboxylic acid-4-sulfopiperidide are distributed in 2000 parts of anhydrous o-dichlorobenzene, and after 150 parts of thionyl chloride and a small amount of pyridine have been added, the temperature is slowly increased to 100 while stirring.
After the temperature has been left at 100 for one hour with stirring, the excess thionyl chloride and some o-dichlorobenzene are distilled off in vacuo, 136.8 parts of 1-amino-4-benzoylaminoanthraquinone are added and the temperature is increased very slowly with stirring 170 to 175. Finally heated. boil for another 10 minutes and let cool.
The dye which precipitates out in very good yield is filtered off and washed with hot alcohol and ether.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257946T | 1944-08-03 | ||
| CH252533T | 1944-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH257946A true CH257946A (en) | 1948-10-31 |
Family
ID=25729636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257946D CH257946A (en) | 1944-08-03 | 1944-08-03 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH257946A (en) |
-
1944
- 1944-08-03 CH CH257946D patent/CH257946A/en unknown
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