CH234530A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH234530A CH234530A CH234530DA CH234530A CH 234530 A CH234530 A CH 234530A CH 234530D A CH234530D A CH 234530DA CH 234530 A CH234530 A CH 234530A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- production
- color
- vat
- parts
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 9
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 2
- 239000000155 melt Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 241001101998 Galium Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005406 washing Methods 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/50—Dibenzopyrenequinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoifes. Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung eines wertvollen Küpenfarbstoffes der Dibenzpyrenchino@nreihe durch Behandeln von Bzl-(3',4'-Dichlorben- zoyl)-benzanthron mit dehydrierenden Mit teln.
Als dehydrierende Mittel kommen die im Hauptpatent erwähnten in Betracht. Der neue Küpenfarbstoff färbt aufs blaustichig roter Küpe Baumwolle in leuchtend goldgel ben Tönen, die mit den Färbungen des nicht substituierten Dibenzpyrenchinonc nahezu farbtongleieh sind.
Der Farbstoff hat eine bedeutend b össere Affinität, ist farbstärker, sodakoch-, wasch- und lichtechter als das Di- pyrenchinon selbist.
Die in dem folgenden Beispiel genannten Teile sind Gewichtsteile.
<I>Beispiel:</I> In -die Schmelze von 600 Teilen wasser freiem Aluminiumohlorid, 120 Tedlen Ka- liumchlorid und 100 Teilen Benzanthron lässt man unter Rühren bei 155-160 im Verlauf von 1 bis ' 2 Stunden 13,0 Teile 8,4-Dibrom- benzoylchlorid eintropfen. und rührt ,die Schmelze noch mehrere Stunden bei der glei chen Temperatur weiter.
Dann zerlegt man sie in der üblichen Weise mit Eis und saugt das ausgeschiedene Bzl-(3',4'-Dibromben- zoyl)-benzanthron ab, wäscht es mit verdünn ter wässeriger Salzsäure, Wasser und Metha nol aus und trocknet es. Die neue Verbindung wird durch Umkristallisieren aus Amylalko- hol in Form gelber Kristalle vom Schmelz punkt 215-220 erhalten.
<B>100</B> Teile dieser Verbindung werden bei 160-135 in eine Schmelze von 1000 Teilen wasserfreiem Aluminiumchlorid und etwa 200 Teilen galiumchlorid eingerührt, worauf die Temperatur auf 155-160 gesteigert und unter raschem Rühren ein lebhafter Sauer stoffstrom in die Schmelze eingeleitet wird.
Nach der üblichen Zerlegung der Schmelze mit Eis wird der ausgeschiedene Farbstoff mit verdünnter wässeriger Schwefelsäure und dann mit Wasser gewaschen und schliesslich durch Verrühren mit 1,2-Dichlorbenzol bei 140-145 von leicht löslichen Verunreini gungen befreit.
Man erhä4t ein orange gefärb tes Mehl, das sich in starker Schwefelsäure mit rotvioletter Farbe lest. Aus blaustichig rot gefärbter Küpe wird Baumwolle in leuch tend goldgelben Tönen gefärbt, die mit -den Färbungen .des nicht substituierten Dibenz- pyrenchinons nahezu farbtongleich sind. Der Farbstoff hat eine bedeutend grössere Affini tät zur Faser als der Grundkörper und ist farbstärker als jener.
Auch die Sadakoch-, Wasch- und Lichtechtheit seiner Färbungen ist beträchtlich besser als diejenige von Fär bungen des Grundkörpers.
Process for the production of a vat dye. The main patent relates to a process for the production of a valuable vat dye of the dibenzpyrenchino @ n series by treating Bzl- (3 ', 4'-dichlorobenzoyl) benzanthrone with dehydrating agents.
Suitable dehydrating agents are those mentioned in the main patent. The new vat dye dyes the bluish red vat of cotton in bright golden-yellow shades, which are almost identical in color to the dyes of the unsubstituted dibenzpyrenquinone.
The dye has a significantly worse affinity, is stronger in color, is more resistant to soda, washing and light than dipyrenequinone itself.
The parts mentioned in the following example are parts by weight.
<I> Example: </I> 13.0 parts 8 are left in the melt of 600 parts of anhydrous aluminum chloride, 120 parts of potassium chloride and 100 parts of benzanthrone while stirring at 155-160 for 1 to 2 hours , Drop in 4-dibromobenzoyl chloride. and stir, the melt continues for several hours at the same temperature.
They are then broken down in the usual way with ice and the precipitated Bzl- (3 ', 4'-dibromobenzoyl) -benzanthrone is sucked off, washed with dilute aqueous hydrochloric acid, water and methanol and dried. The new compound is obtained by recrystallization from amyl alcohol in the form of yellow crystals with a melting point of 215-220.
100 parts of this compound are stirred into a melt of 1000 parts of anhydrous aluminum chloride and about 200 parts of galium chloride at 160-135, whereupon the temperature is increased to 155-160 and a vigorous stream of oxygen flows into the melt with rapid stirring is initiated.
After the usual breakdown of the melt with ice, the precipitated dye is washed with dilute aqueous sulfuric acid and then with water and finally freed from easily soluble impurities by stirring with 1,2-dichlorobenzene at 140-145.
An orange colored flour is obtained which dissolves in strong sulfuric acid with a red-violet color. From a blue-tinged red vat, cotton is dyed in bright golden-yellow tones, which are almost identical in color to the dyes of the unsubstituted dibenzene-pyrenequinone. The dye has a significantly greater affinity for the fiber than the basic body and is stronger in color than that.
The Sado-cook, wash and lightfastness of its dyeings is considerably better than that of dyeings of the base body.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE234530X | 1939-02-25 | ||
| CH232372T | 1943-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH234530A true CH234530A (en) | 1944-09-30 |
Family
ID=25727707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH234530D CH234530A (en) | 1939-02-25 | 1943-02-05 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH234530A (en) |
-
1943
- 1943-02-05 CH CH234530D patent/CH234530A/en unknown
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