CH259729A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH259729A CH259729A CH259729DA CH259729A CH 259729 A CH259729 A CH 259729A CH 259729D A CH259729D A CH 259729DA CH 259729 A CH259729 A CH 259729A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- red
- production
- parts
- vat
- Prior art date
Links
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
Zusatzpatent zum Hauptpatent Nr. 243843. Verfahren zur Herstellung eines Küpenfarbstoges. Es wurde befunden, @dass ein wertvoller Kilpenfarb.:toff herbestellt werden kann, wenn man 1 Mol eines funktionellen Deri vats einer Anthrachinon - 2;
6 - diearb-o.nsäure, die in 1- und 5-.Stellung je einen austausch baren Substituenten enthält, mit 2 Mol l.- Amino-5-benzoylaminoanthraehinon umsetzt und hierauf die Substituenten in 1- und 5- Stellung der Säurekomponente durch Behand- 1unb mit einem Sulfonsäureamid und Abspaltung des
Sulfonsä.ureesters geben Aminogruppen austauscht.
Der neue Farbstoff ist, ein rotbraunes Pulver, das .sich in konzentrierter Schwefel säure mit roter Farbe löst und Baumwolle aus schwarzoliver Küpe in blaustichig rot- braunen Tönen färbt.
Substituenten, die sich gegen eine Amino- bruppe austauschen lassen, sind beispiels weise Halogenatome. Als Sulfonsäureamid kann beispielsweise p-Toluolsulfonamid ver wendet werden.
Zur Durchführung der Umsetzung mit den Aminokomponenten kann als funktionelles Derivat der Säurekomponente 'beispielsweise das Säurechlorid verwendet werden. Die Re aktion wird zweckmässig in einem indifferen ten Lösungs- bzw. Verteilungsmittel vorge nommen, wobei insbesondere solche von hö herem 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> 18,8 Teile 1,5 - Dichloranfhraühinon - 2,6- dicarbon:säure, erhalten dureh Oxydation von 1,5 - Di-chlor - 2,6 - dimethylanthra,chinon mit Braunstein in 8'Oprozentiger Schwefelsäure bei 80 , werden durch Erhitzen mit 20 Teilen Thiony lchlorid in 750 Teilen troek@enem o Dichlorbenzol in das Säurechlorid verwandelt.
Nach dem Ab,destillieren des unverbrauchten Thionylchlorids lässt man bei 150 eine heisse Lösung von, 34,2, Teilen 1-A.mino-,5 benizoyl- aminoanthraehinon in 35,0 Teilen o-Dichlor- benzol zufliessen.
Nach zweistündigem Rüh ren bei 15,0 bis 1-610 ist. die Farbstoffbildung beendet. Man saugt in der Wärme ab, wäscht mit Diehlorhenzol und Alkohol aus und trocknet.
2'5,3 Teile .des, ,so erhaltenen Produktes wer den mit 1-0,3 Teilen p-T'oluolsulfamid, 5,8 Teilen Ka.liumaeeta.t und 0;6 Teilen Kupfer acetat in 200 Teilen trockenem Nitrobenzol während 7 Stunden unter Rühren zum Sie den erhitzt.
Nach dem Erkalten wird fil triert, mit: Alkohol, verdünnter Salzsäure und Wasser bew asehen und betroeknet. Zur Ab spaltung der Toluolsulfonsäuregruppen: trägt man das s o erhaltene Umsetzungserzeugnis in 500 Teile konzentrierte Schwefelsäure ein und rührt während 5 Stunden bei 2i0 . Nun trägt man die rot gefärbte Lösung auf Eis aus, filtriert den ausgefallenen Farbstoff ab, wäscht ihn mit Wasser aus und trocknet.
Additional patent to main patent no. 243843. Process for the production of a vat dye. It has been found that a valuable Kilpenfarb.:toff can be obtained by adding 1 mole of a functional derivative of an anthraquinone - 2;
6 - diearb-o.nsäure, which contains an exchangeable substituent in each of the 1- and 5- position, with 2 moles of 1- amino-5-benzoylaminoanthraehinone and then the substituents in the 1- and 5- position of the acid component through Treat 1unb with a sulfonic acid amide and split off the
Sulfonsä.ureesters give amino groups exchanges.
The new dye is a red-brown powder, which dissolves in concentrated sulfuric acid with a red color and dyes cotton from a black-olive vat in bluish red-brown tones.
Substituents that can be exchanged for an amino group are, for example, halogen atoms. As sulfonic acid amide, for example, p-toluenesulfonamide can be used.
The acid chloride, for example, can be used as the functional derivative of the acid component to carry out the reaction with the amino components. The reaction is expediently carried out in an indifferent solvent or distribution medium, particularly those with a higher boiling point such as chlorobenzene, nitrobenzene or dichlorobenzene. The reaction can be carried out, for example, at elevated temperature, in the presence or absence of acid-binding agents.
<I> Example: </I> 18.8 parts 1,5 - Dichloranfhraühinon - 2,6- dicarbon: acid, obtained by oxidation of 1,5 - Di-chloro - 2,6 - dimethylanthra, quinone with manganese dioxide in 8 'O per cent sulfuric acid at 80 is converted into the acid chloride by heating with 20 parts of thionyl chloride in 750 parts of troek @ enem o dichlorobenzene.
After the unused thionyl chloride has been distilled off, a hot solution of 34.2 parts of 1-A.mino.5 benizoylaminoanthraehinone in 35.0 parts of o-dichlorobenzene is allowed to flow in at 150.
After stirring for two hours, it is at 15.0 to 1-610. the dye formation ends. It is suctioned off in the heat, washed with diehlorhenzene and alcohol and dried.
2.5.3 parts of the product obtained in this way with 1-0.3 parts of p-toluenesulfamide, 5.8 parts of potassium aeeta.t and 0.6 parts of copper acetate in 200 parts of dry nitrobenzene during 7 hours with stirring to the heated.
After it has cooled down, it is filtered, treated with: alcohol, dilute hydrochloric acid and water and thrown out. To split off the toluenesulphonic acid groups: the reaction product obtained in this way is introduced into 500 parts of concentrated sulfuric acid and stirred for 5 hours at 2.10. The red colored solution is now poured onto ice, the precipitated dye is filtered off, washed out with water and dried.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH243843T | 1943-06-24 | ||
CH259729T | 1943-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH259729A true CH259729A (en) | 1949-01-31 |
Family
ID=25728850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH259729D CH259729A (en) | 1943-06-24 | 1943-06-24 | Process for the production of a vat dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH259729A (en) |
-
1943
- 1943-06-24 CH CH259729D patent/CH259729A/en unknown
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