CH247609A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH247609A CH247609A CH247609DA CH247609A CH 247609 A CH247609 A CH 247609A CH 247609D A CH247609D A CH 247609DA CH 247609 A CH247609 A CH 247609A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- production
- dye
- red
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- DOTXURRYSTUNKM-UHFFFAOYSA-N 1,5-diamino-9,10-dioxoanthracene-2,6-dicarboxylic acid Chemical class NC1=C(C=CC=2C(C3=C(C(=CC=C3C(C1=2)=O)C(=O)O)N)=O)C(=O)O DOTXURRYSTUNKM-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 description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HUICBIWCAKSDRB-UHFFFAOYSA-N 1,5-diamino-9,10-dioxoanthracene-2,6-dicarbonyl chloride Chemical compound NC1=C(C=CC=2C(C3=C(C(=CC=C3C(C1=2)=O)C(=O)Cl)N)=O)C(=O)Cl HUICBIWCAKSDRB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material 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
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/32—1.3 azoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 243843. Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1 Mol eines funktionellen Deri vats der 1,5-Diaminoanthrachinon-2,6-di- carbonsäure mit 1 Mol 1-Amino-5-benzoyl- aminoanthrachinon und 1 Mol Anilin umsetzt.
Der neue Farbstoff ist ein dunkelrot- braunes Pulver, das sich in konzentrierter .Schwefelsäure mit braunroter Farbe löst und Baumwolle aus oliveschwarzer güpe in blau stichig rotbraunen Tönen färbt.
Zur Durchführung der Umsetzung kann als funktionelles Derivat der genannten Di- carbonsäure beispielsweise das Säurechlorid verwendet werden. Die Reaktion wird zweck mässig in einem indifferenten Lösungs- bezw. Verteilungsmittel vorgenommen, wobei ins besondere solche von höherem Siedepunkt, wie Chlorbenzol, Nitrobenzol oder Dichlor- benzol in Betracht kommen. Man kann die Umsetzung beispielsweise bei erhöhter Tem peratur, in An- oder Abwesenheit säure bindender Mittel durchführen.
Zweckmässig bringt man die beiden Aminkomponenten nacheinander zur Reaktion. <I>Beispiel:</I> 8,6 Teile 1-Amino-5-benzoylaminoanthra- chinon, 9,1 Teile 1,5-Diaminoanthrachinon- 2,6-dicarbonsäurechlorid, 2,5 Teile Pyridin und 600 Teile trockenes Nitrobenzol werden zusammen so lange bei 45 bis 55 gerührt, bis alles Ausgangsmaterial umgesetzt ist. Nun erhitzt man auf 150 , gibt 10 Teile Ani lin hinzu und rührt zur Beendigung der Farb- stoffbildung 2 Stunden bei 150 bis 160 nach.
Der entstandene Farbstoff wird in der Wärme abgesaugt, mit Nitrobenzol und Alkohol gewaschen und getrocknet.
Additional patent to the main patent No. 243843. Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1 mol of a functional derivative of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid with 1 mol of 1-amino-5-benzoylaminoanthraquinone and 1 mol of aniline implements.
The new dye is a dark red-brown powder that dissolves in concentrated sulfuric acid with a brownish-red color and dyes cotton from olive-black güpe in blue-tinged red-brown tones.
The acid chloride, for example, can be used as the functional derivative of the dicarboxylic acid mentioned to carry out the reaction. The reaction is expediently in an indifferent solution or. Made distribution means, in particular those with a higher boiling point, such as chlorobenzene, nitrobenzene or dichlorobenzene come into consideration. The reaction can be carried out, for example, at elevated temperature, in the presence or absence of acid-binding agents.
The two amine components are expediently reacted one after the other. <I> Example: </I> 8.6 parts of 1-amino-5-benzoylaminoanthraquinone, 9.1 parts of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid chloride, 2.5 parts of pyridine and 600 parts of dry nitrobenzene stirred together at 45 to 55 until all of the starting material has reacted. The mixture is then heated to 150, 10 parts of aniline are added and the mixture is subsequently stirred at 150 to 160 for 2 hours to complete the formation of the dye.
The resulting dye is filtered off with suction while warm, washed with nitrobenzene and alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH247609T | 1943-06-24 | ||
| CH243843T | 1943-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH247609A true CH247609A (en) | 1947-03-15 |
Family
ID=25728843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH247609D CH247609A (en) | 1943-06-24 | 1943-06-24 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH247609A (en) |
-
1943
- 1943-06-24 CH CH247609D patent/CH247609A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1026456B (en) | Process for the production of Kuepen dyes | |
| CH247609A (en) | Process for the production of a vat dye. | |
| DE1154586B (en) | Process for the preparation of anthraquinone dyes | |
| DE1079762B (en) | Process for the production of Kuepen dyes of the thiazole and oxazole series | |
| DE1006557C2 (en) | Process for the production of anthraquinone dyes | |
| DE867725C (en) | Process for the production of Kuepen dyes | |
| DE525331C (en) | Process for the production of new Kuepen dyes | |
| DE600102C (en) | Process for the representation of dyes | |
| DE855144C (en) | Process for the production of Kuepen dyes | |
| AT72226B (en) | Process for the preparation of arylaminoanthraquinone dyes. | |
| AT55690B (en) | Process for the preparation of anthraquinone derivatives. | |
| DE841615C (en) | Process for the production of Kuepen dyes of the anthraquinone series | |
| DE366734C (en) | Process for the production of sulfur-containing Kuepen dyes | |
| CH243843A (en) | Process for the production of a vat dye. | |
| DE40375C (en) | Process for the production of a dye called "styrogallol" from gallic acid or tannin | |
| DE936945C (en) | Process for the production of Kuepen dyes | |
| CH247606A (en) | Process for the production of a vat dye. | |
| CH265734A (en) | Process for the production of a vat dye. | |
| CH247608A (en) | Process for the production of a vat dye. | |
| CH259729A (en) | Process for the production of a vat dye. | |
| CH247612A (en) | Process for the production of a vat dye. | |
| CH247605A (en) | Process for the production of a vat dye. | |
| CH247603A (en) | Process for the production of a vat dye. | |
| CH247607A (en) | Process for the production of a vat dye. | |
| CH265735A (en) | Process for the production of a vat dye. |