CH247603A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH247603A CH247603A CH247603DA CH247603A CH 247603 A CH247603 A CH 247603A CH 247603D A CH247603D A CH 247603DA CH 247603 A CH247603 A CH 247603A
- Authority
- CH
- Switzerland
- Prior art keywords
- dicarboxylic acid
- acid
- production
- vat dye
- dye
- 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 claims description 3
- 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 4
- ZUTFCPOKQHJATC-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ZUTFCPOKQHJATC-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
- 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
- 150000004820 halides Chemical class 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 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 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 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 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
- JNEPEKOSCSQPHH-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C2C(=O)C3=CC(C(=O)Cl)=CC=C3C(=O)C2=C1 JNEPEKOSCSQPHH-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
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
- 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
- C09B1/43—Dicarboxylic acids
-
- 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. Zusatzpatent zum Hauptpatent Nr. 243843. Es wurden gefunden, dassi ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1 Mol Anthrachinon-2,
6-dicarbon- säure oder eines ihrer funktionellen Derivate mit 2 Mol 1-Amino-5-benzoylaminoanthrachi- non umsetzt.
Der neue Farbstoff ist ein gelbes Pulver, das sich in konz. Schwefelsäure mit roter Farbe löst und Baumwolle aus rötlicholiver Küpe in gelben 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> 16,7 Teile Anthrachinon - 2,6 - dicarbon- säurechlorid, das z. B. aus Anthrachinon-2,6- dicarbonsäure nach Monatshefte für Chemie, Band 32, Seite 164 dargestellt werden kann, und 500 Teile trockenes o-Dichlorbenzol werden unter Rühren auf 150-160 erhitzt und bei dieser Temperatur mit einer heissen Lösung von 34,2 Teilen 1-Amino-5-benzoyl- aminoanthrachinon in 750 Teilen o-Dichlor- benzol versetzt.
Nach zweistündigem Rühren bei 150-160 ist die Farbstoffbildung be endet. Man saugt den auskristallisierten Farbstoff in der Wärme ab, wäscht ihn mit o-Dichlorbenzol und Alkohol aus und trock net ihn.
process for the production of a vat dye. Additional patent to the main patent No. 243843. It has been found that a valuable vat dye can be produced if 1 mole of anthraquinone-2,
6-dicarboxylic acid or one of its functional derivatives is reacted with 2 moles of 1-amino-5-benzoylaminoanthraquinone.
The new dye is a yellow powder that is in conc. Sulfuric acid dissolves red and dyes cotton from a reddish-olive vat in yellow tones.
To carry out the reaction, said dicarboxylic acid or preferably one of its functional derivatives, for example an acid halide and in particular the acid chloride, can be used. 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 come into consideration. The reaction can be carried out, for example, at elevated temperature, in the presence or absence of acid-binding agents.
<I> Example: </I> 16.7 parts of anthraquinone - 2.6 - dicarboxylic acid chloride, the z. B. from anthraquinone-2,6-dicarboxylic acid according to the monthly magazine for chemistry, volume 32, page 164, and 500 parts of dry o-dichlorobenzene are heated with stirring to 150-160 and at this temperature with a hot solution of 34, 2 parts of 1-amino-5-benzoylaminoanthraquinone in 750 parts of o-dichlorobenzene are added.
After two hours of stirring at 150-160, dye formation is over. The dyestuff which has crystallized out is suctioned off in the heat, washed out with o-dichlorobenzene and alcohol and dried out.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243843T | 1943-06-24 | ||
| CH247603T | 1943-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH247603A true CH247603A (en) | 1947-03-15 |
Family
ID=25728837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH247603D CH247603A (en) | 1943-06-24 | 1943-06-24 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH247603A (en) |
-
1943
- 1943-06-24 CH CH247603D patent/CH247603A/en unknown
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