CH128472A - Process for the preparation of a dye of the benzanthrone series. - Google Patents
Process for the preparation of a dye of the benzanthrone series.Info
- Publication number
- CH128472A CH128472A CH128472TA CH128472A CH 128472 A CH128472 A CH 128472A CH 128472T A CH128472T A CH 128472TA CH 128472 A CH128472 A CH 128472A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- parts
- nitro
- benzanthrone series
- Prior art date
Links
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000000391 smoking effect Effects 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
- C09B3/78—Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
- C09B3/80—Preparation by synthesis of the nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Farbstoffes der Benzanthronreihe. Es wurde gefunden, dass man einen neuen Farbstoff der Benzanthronreihe erhält, wenn man Bz-1-Nitro-2-methylbenzanthron mit oder ohne Zusatz eines indifferenten Lö- sungs- oder Verdünnungsmittels mit sauren Kondensationsmitteln behandelt.
Als geeignete saure Kondensationsmittel seien genannt:. Rauchende Schwefelsäure, Chlorsulfonsäure oder Mischungen beider, Aluminiumchlorid usw.
Der so erhaltene Farbstoff ist trocken ein schwärzliches Pulver, praktisch unlöslich in organischen Lösungsmitteln, löslich in konzentrierter Schwefelsäure mit olivegrüner Farbe. Er liefert mit Hydrosulfit und Lauge eine blaurote Küpe, aus der Baumwolle in grauschwarzen Tönen von guten Echtheits eigenschaften angefärbt wird.
<I>Beispiel 1:</I> 50 Teile Bz-1-Nitro-2-methylbenzanthron werden bei 10 in 250 Teilen 60 %iges Oleum eingetragen und die Lösung kurze Zeit bis zur Beendigung der Farbstoffbildung nach gerührt. Die Schmelze wird dann durch Zu- laufenlassen von 250 Teilen 90 %iger Schwefelsäure bei 10 bis 20' verdünnt. Hierauf lässt man die Masse auf Eis fliessen und filtriert das abgeschiedene Reaktions produkt ab. Durch Auskochen mit ver dünnter Natronlauge kann dieses von etwa vorhandenen Verunreinigungen befreit wer den.
Beispiel <I>2:</I> In ein Gemisch von 100 Teilen 70 %igem Oleum und 50 Teilen Chlorsulfonsäure trägt man zismlich schnell bei einer Temperatur von - 5 bis 0 10 Teile fein gepulvertes Bz-1-Nitro-2-methylbenzanthron ein und rührt die Masse etwa eine halbe Stunde bei der gleichen Temperatur. Hierauf giesst man in viel Wasser, filtriert und befreit von der Mineralsäure durch Auswaschen mit Was ser. Der so erhaltene Farbstoff stimmt mit dem des Beispiels 1 überein.
<I>Beispiel 3:</I> Ein Gemisch von 10 Teilen Bz-1-Nitro-2- methylbenzanthron, 10 Teilen fein gepulver- tem Aluminiumchlorid und<B>100</B> '.'eilen Tri- chlorbenzol wird sechs Stunden unter gutem Rühren unter Rückfluss gekocht. Man lässt etwas abkühlen, versetzt mit Wasser und treibt das Trichlorbenzol mit Wasserdampf ab. Zur vollständigen Entfernung von Ton erdesalzen kocht man noch mit verdünnter Salzsäure aus.
Der Farbstoff stimmt mit dem des Beispiels 1 überein.
Process for the preparation of a dye of the benzanthrone series. It has been found that a new dye of the benzanthrone series is obtained if Bz-1-nitro-2-methylbenzanthrone is treated with acidic condensing agents with or without the addition of an inert solvent or diluent.
Suitable acidic condensing agents are: Smoking sulfuric acid, chlorosulfonic acid or mixtures of both, aluminum chloride, etc.
The dye thus obtained is a blackish powder when dry, practically insoluble in organic solvents, soluble in concentrated sulfuric acid with an olive-green color. With hydrosulfite and lye, it supplies a blue-red vat from which cotton is dyed in gray-black tones with good fastness properties.
<I> Example 1: </I> 50 parts of Bz-1-nitro-2-methylbenzanthrone are introduced at 10 in 250 parts of 60% oleum and the solution is stirred for a short time until the formation of the dye has ended. The melt is then diluted at 10 to 20 minutes by running in 250 parts of 90% strength sulfuric acid. The mass is then allowed to flow on ice and the separated reaction product is filtered off. This can be freed of any impurities by boiling with dilute sodium hydroxide solution.
Example <I> 2: </I> 10 parts of finely powdered Bz-1-nitro-2-methylbenzanthrone are introduced into a mixture of 100 parts of 70% oleum and 50 parts of chlorosulphonic acid at a temperature of -5 to 0 and stir the mass for about half an hour at the same temperature. It is then poured into plenty of water, filtered and freed from the mineral acid by washing with water. The dye obtained in this way corresponds to that of Example 1.
Example 3: A mixture of 10 parts of Bz-1-nitro-2-methylbenzanthrone, 10 parts of finely powdered aluminum chloride and 100 parts of trichlorobenzene becomes six Boiled under reflux for hours with thorough stirring. It is allowed to cool slightly, water is added and the trichlorobenzene is driven off with steam. To completely remove clay earth salts, boil them with dilute hydrochloric acid.
The dye is identical to that of Example 1.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128472T CH128472A (en) | 1927-06-10 | 1927-06-10 | Process for the preparation of a dye of the benzanthrone series. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128472T CH128472A (en) | 1927-06-10 | 1927-06-10 | Process for the preparation of a dye of the benzanthrone series. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH128472A true CH128472A (en) | 1928-11-01 |
Family
ID=4386939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128472T CH128472A (en) | 1927-06-10 | 1927-06-10 | Process for the preparation of a dye of the benzanthrone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH128472A (en) |
-
1927
- 1927-06-10 CH CH128472T patent/CH128472A/en unknown
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