CH247607A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH247607A CH247607A CH247607DA CH247607A CH 247607 A CH247607 A CH 247607A CH 247607D A CH247607D A CH 247607DA CH 247607 A CH247607 A CH 247607A
- Authority
- CH
- Switzerland
- Prior art keywords
- dicarboxylic acid
- acid
- vat
- dye
- diaminoanthraquinone
- 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 description 2
- 239000000975 dye Substances 0.000 claims description 5
- DOTXURRYSTUNKM-UHFFFAOYSA-N 1,5-diamino-9,10-dioxoanthracene-2,6-dicarboxylic acid Chemical compound 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000004820 halides Chemical class 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 10
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1 Mol 1,5-Diaminoanthrachinon- 2.6-dicarbonsäure oder eines ihrer funktionel len Derivate mit 2 Mal 4-Aminoanthrachinon- 2,1(N)-1',2'(N)-benza.ciidon umsetzt.
Der neue Farbstoff ist ein dunkles Pulver, das sich in konz. Schwefelsäure mit orange roter Farbe löst und Baumwolle aus rot violetter Küpe in blaustichig violetten Tönen färbt.
Zur Durchführung der Umsetzung kann die genannte Dicarbonsäure oder vorzugs weise eines ihrer funktionellen Derivate, bei spielsweise ein Säurehalogenid und insbeson dere das Säurechlorid verwendet werden. Die Reaktion wird zweckmässig in einem indiffe renten Lösungs- bezw. Verteilungsmittel vor genommen, wobei insbesondere solche von höherem Siedepunkt, wie Chlorbenzol, Nitro- benzol oder Dichlorbenzol, in Betracht kom men. Man kann die Umsetzung beispielsweise bei erhöhter Temperatur, in An- oder Ab wesenheit säurebindender Mittel durchführen.
<I>Beispiel:</I> Zu der Lösung von 17 Teilen 4-Amino- anthrachinon-2,1(N)-1',2'(N)-benzacridon in 500 Teilen trockenem Nitrobenzol gibt man bei 90-100 9,1 Teile 1,5-Diaminoanthrachi- non-2,6-dicarbonsäurechlorid. Hierauf steigert man die Temperatur innert 2/, Stunde auf 150 . Zur Beendigung der Farbstoffbildung rührt man noch 2 Stunden bei 150-160 , filtriert dann in der Wärme ab, wäscht mit Nitrobenzol und Alkohol aus und trocknet.
Das in diesem Beispiel verwendete Säure chlorid kann wie folgt erhalten werden: 5 Teile 1,5-Diaminoanthrachinon-2,6-di- carbonsäure werden mit 60 Teilen trockenem Nitrobenzol vermahlen. Zu der feinen Sus pension gibt man nun weitere 540 Teile trockenes Nitrobenzol, 1 Teil Pyridin und 17 Teile Thionylchlorid hinzu und erhitzt das Gemisch während i/,4 Stunde auf 90-100 . Dabei geht die 1,5-Diaminoanthrachinon-2,6- dicarbonsäure in Lösung. Man filtriert von einigen Verunreinigungen ab und lässt das Filtrat erkalten.
Das 1,5-Diaminoanthrachi- non-2,6-dicarbonsäurechlorid kristallisiert in grünlich schillernden, rotbraunen Nadeln aus. Es wird abgesaugt, mit Aceton und Wasser (zur Entfernung von salzsaurem Pyridin) ge waschen und im Exsiccator getrocknet.
Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if 1 mol of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid or one of its functional len derivatives with 2 times 4-aminoanthraquinone-2,1 (N) -1 ', 2' (N) -benza.ciidon converts.
The new dye is a dark powder that is in conc. Sulfuric acid dissolves with an orange-red color and dyes cotton from a red-violet vat in bluish violet tones.
The dicarboxylic acid mentioned or preferably one of its functional derivatives, for example an acid halide and in particular the acid chloride, can be used to carry out the reaction. The reaction is expediently in an indifferent solution or. Distribution agents taken before, in particular those with a higher boiling point, such as chlorobenzene, nitrobenzene or dichlorobenzene, are suitable. The reaction can be carried out, for example, at elevated temperature, in the presence or absence of acid-binding agents.
<I> Example: </I> 9 is added at 90-100 to the solution of 17 parts of 4-aminoanthraquinone-2,1 (N) -1 ', 2' (N) -benzacridone in 500 parts of dry nitrobenzene , 1 part of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid chloride. The temperature is then increased to 150 within 2.5 hours. To complete the formation of the dye, the mixture is stirred for a further 2 hours at 150-160, then filtered off in the heat, washed with nitrobenzene and alcohol and dried.
The acid chloride used in this example can be obtained as follows: 5 parts of 1,5-diaminoanthraquinone-2,6-dicarboxylic acid are ground with 60 parts of dry nitrobenzene. A further 540 parts of dry nitrobenzene, 1 part of pyridine and 17 parts of thionyl chloride are then added to the fine suspension, and the mixture is heated to 90-100 for 1/4 hour. The 1,5-diaminoanthraquinone-2,6-dicarboxylic acid goes into solution. Some impurities are filtered off and the filtrate is allowed to cool.
The 1,5-diaminoanthraquinone-2,6-dicarboxylic acid chloride crystallizes out in greenish shimmering, red-brown needles. It is filtered off with suction, washed with acetone and water (to remove hydrochloric acid pyridine) and dried in a desiccator.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243843T | 1943-06-24 | ||
| CH247607T | 1943-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH247607A true CH247607A (en) | 1947-03-15 |
Family
ID=25728841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH247607D CH247607A (en) | 1943-06-24 | 1943-06-24 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH247607A (en) |
-
1943
- 1943-06-24 CH CH247607D patent/CH247607A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1026456B (en) | Process for the production of Kuepen dyes | |
| CH247607A (en) | Process for the production of a vat dye. | |
| CH247608A (en) | Process for the production of a vat dye. | |
| CH247605A (en) | Process for the production of a vat dye. | |
| CH247604A (en) | Process for the production of a vat dye. | |
| CH247606A (en) | Process for the production of a vat dye. | |
| DE709690C (en) | Process for the preparation of N-substituted pyrazole anthrones | |
| DE1079762B (en) | Process for the production of Kuepen dyes of the thiazole and oxazole series | |
| CH243843A (en) | Process for the production of a vat dye. | |
| AT52957B (en) | Process for the preparation of vat dyes. | |
| DE867725C (en) | Process for the production of Kuepen dyes | |
| DE855144C (en) | Process for the production of Kuepen dyes | |
| DE728375C (en) | Process for the production of Kuepen dyes of the dibenzanthrone series | |
| CH247611A (en) | Process for the production of a vat dye. | |
| DE536826C (en) | Process for the preparation of Kuepen dyes of the anthraquinone series | |
| CH247609A (en) | Process for the production of a vat dye. | |
| CH251804A (en) | Process for the production of a vat dye. | |
| CH247612A (en) | Process for the production of a vat dye. | |
| DE1445738A1 (en) | Process for the preparation of anthraquinone dyes | |
| CH257947A (en) | Process for the production of a vat dye. | |
| CH259729A (en) | Process for the production of a vat dye. | |
| CH247603A (en) | Process for the production of a vat dye. | |
| CH251802A (en) | Process for the production of a vat dye. | |
| CH251803A (en) | Process for the production of a vat dye. | |
| CH292691A (en) | Process for the production of a vat dye. |