CH257950A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH257950A CH257950A CH257950DA CH257950A CH 257950 A CH257950 A CH 257950A CH 257950D A CH257950D A CH 257950DA CH 257950 A CH257950 A CH 257950A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- acid
- process according
- production
- vat
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000002253 acid Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 claims description 2
- PURCZXCDZQICPW-UHFFFAOYSA-N n-(benzylsulfamoyl)-1-phenylmethanamine Chemical group C=1C=CC=CC=1CNS(=O)(=O)NCC1=CC=CC=C1 PURCZXCDZQICPW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012442 inert solvent 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
<B>Zusatzpatent</B> zum Hauptpatent Nr. 252583. Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1-Amino-5-benzoylamino-anbhra- chinon mit einem funktionellen Derivat der in 4-,Stellung durch eine Dibenzylsulfamid- gruppe substituierten Benzol-l-earbonsäure umsetzt.
Der neue Farbstoff bildet ein gelbes kri stallines Pulver, löst sich in konz. Schwefel säure mit roter Farbe und färbt Baumwolle aus rotstickig violetter Küpe in grünstickig gelben 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 Siede punkt, wie Mono-, Ds- oder Trichlorbenzol. vorgenommene werden, wobei vorteilhaft bei erhöhter Temperatur gearbeitet wird.
Das für das vorliegende Verfahren be- nötigte Benzol-l-carbons5,ure-4-sulfodübenzyl- amid kann beispielsweise durch Umsetzen von Benzol-l-carbonsäure-4-sulfochlorid mit einer wässerigen alkoholischen Lösung von Dibenzylamin hergestellt werden.
<I>Beispiel:</I> 25,4 Teile Benzol-l-carbonsäure-4-sulfo- dibenzylamid werden in 1000 Teilen wasser freiem o-Dichlorbenzol verteilt und nach Zu- fügen von 90 Teilen Thionylchlorid und einer geringen Menge Pyridin wird die Tem peratUr langsam unter Rühren auf 100 ge steigert.
Nachdem die Temperatur 30 Minu ten unter Rühren bei 100 bis 1l0 belassen wurde, destilliert man das überschüssige Thionylchlorid und etwas; o-Dichlorbenzol ab, gibt 22,8 Teile 1-Amino-5-benzoylamino- anthrachinon hinzu und steigert die Tem peratur unter Rühren langsam zum Sieden. Nach dem Erkalten wird filtriert und gut mit heissem Alkohol und Äther gewaschen.
Gewünschtenfalls kann der Farbstoff aus Pyridin umgefällt werden; er liefert dann, in manchen Fällen besonders kräftige und reine Töne.
<B> Additional patent </B> to main patent no. 252583. Process for the production of a vat dye. It has been found that a valuable vat dye can be produced by reacting 1-amino-5-benzoylamino-Anbhraquinone with a functional derivative of the benzene-1-carboxylic acid substituted in the 4- position by a dibenzylsulfamide group.
The new dye forms a yellow crystalline powder, dissolves in conc. Sulfuric acid with red color and dyes cotton from a red-tinged violet vat in green-tinged yellow 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, for example, in an inert solvent, preferably of a relatively high boiling point, such as mono-, ds- or trichlorobenzene. are made, it is advantageous to work at elevated temperature.
The benzene-1-carboxylic acid-4-sulfodubenzylamide required for the present process can be prepared, for example, by reacting benzene-1-carboxylic acid-4-sulfochloride with an aqueous alcoholic solution of dibenzylamine.
<I> Example: </I> 25.4 parts of benzene-1-carboxylic acid-4-sulfodibenzylamide are distributed in 1000 parts of anhydrous o-dichlorobenzene and, after adding 90 parts of thionyl chloride and a small amount of pyridine, the The temperature slowly increased to 100 while stirring.
After the temperature was left for 30 minutes with stirring at 100 to 10, the excess thionyl chloride and something are distilled off; o-Dichlorobenzene, 22.8 parts of 1-amino-5-benzoylamino-anthraquinone are added and the temperature slowly increases to boiling while stirring. After cooling, it is filtered and washed well with hot alcohol and ether.
If desired, the dye can be reprecipitated from pyridine; in some cases it delivers particularly strong and pure tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257950T | 1944-08-03 | ||
| CH252533T | 1944-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH257950A true CH257950A (en) | 1948-10-31 |
Family
ID=25729640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257950D CH257950A (en) | 1944-08-03 | 1944-08-03 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH257950A (en) |
-
1944
- 1944-08-03 CH CH257950D patent/CH257950A/en unknown
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