DE186596C - - Google Patents
Info
- Publication number
- DE186596C DE186596C DENDAT186596D DE186596DA DE186596C DE 186596 C DE186596 C DE 186596C DE NDAT186596 D DENDAT186596 D DE NDAT186596D DE 186596D A DE186596D A DE 186596DA DE 186596 C DE186596 C DE 186596C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- red
- alcohol
- yellow
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000984 vat dye Substances 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
- C09B3/40—Pyranthrones
- C09B3/44—Preparation from starting materials already containing the pyranthrone nucleus
- C09B3/46—Preparation from starting materials already containing the pyranthrone nucleus by halogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 186596 KLASSE 22 b. GRUPPE- M 186596 CLASS 22 b. GROUP
In der Patentschrift 175067 ist ein Verfahren zur Darstellung neuer Anthracenderivate beschrieben, darin bestehend, daß man 2 · 2'-Dimethyl-1 · i'-dianthrachinonyl oder dessen Derivate für sich erhitzt oder mit wasserentziehenden Mitteln behandelt. Wie dann in der Patentschrift 174494 gezeigt worden ist, besitzen diese Körper die typischen Eigenschaften von Küpenfarbstoffen, indem sie z. B. aus alkalischem, hydrosulfithaltigem Bade Baumwolle in rötlichgelbbisgelb anfärben. Es hat sich nun gezeigt, daß man zu Farbstoffen gelangen kann, welche Baumwolle in rotstichigeren Tönen anfärben, wenn man die gemäß der Patentschrift 175067 erhältlichen Produkte mit Halogenen oder halogenentwickelnden Mitteln behandelt. Die erhaltenen Produkte, die sich äußerlich kaum von den Ausgangsmaterialien unterscheiden, färben Baumwolle aus kirschrot gefärbten Küpen in lebhaften blauroten Tönen an, welche beim Waschen in leuchtendes orangerot übergehen. In the patent 175067 is a method for the preparation of new anthracene derivatives described, consisting in that 2 · 2'-dimethyl-1 · i'-dianthraquinonyl or its derivatives heated by themselves or treated with dehydrating agents. As has then been shown in patent specification 174494, these bodies have the typical ones Properties of vat dyes by e.g. B. from alkaline, hydrosulfite Dye bath cotton in reddish yellow to yellow. It has now been shown that dyes can be obtained which cotton in Color with more reddish tones, if you get the according to the patent 175067 available Products treated with halogens or halogen-generating agents. The received Cotton made from cherry-red dyed products that hardly differ from the raw materials on the outside Vats in lively blue-red tones, which turn into bright orange-red when washed.
Die nach vorliegendem Verfahren erhältliehen Verbindungen sind von dem in Beispiel 10 des französischen Patents 357239 beschriebenen, aus 4 · 4'-Dichlor-2 · 2 '-Dimethyl -ι · 1'-Dianthrachinonyl dargestellten Produkt verschieden. Dieses ist in der Nuance den nichtchlorierten Farbstoffen, die bei vorliegendem Verfahren als Ausgangsmaterial verwendet werden, praktisch gleich.The compounds obtained by the present process are the same as in Example 10 of French patent 357239, from 4x4'-dichloro-2x2'-dimethyl -ι · 1'-Dianthraquinonyl shown Product different. This is in the shade of the non-chlorinated dyes that are used as starting material in the present process, practically the same.
10 Teile des Produkts, erhalten nach Beispiel I bis 4 der Patentschrift 175067, werden mit ι oo Teilen Nitrobenzol innig gemischt und bei gewöhnlicher Temperatur mit 7 Teilen Sulfurylchlorid versetzt.10 parts of the product obtained according to Example I to 4 of patent 175067 are intimately mixed with ι oo parts of nitrobenzene and at ordinary temperature with 7 parts Sulfuryl chloride added.
Man erwärmt die Mischung dann während 3 Stunden unter Rühren auf 60 bis 700, verdünnt nach dem Erkalten mit 100 Teilen Alkohol, filtriert und wäscht mit Alkohol eventuell noch mit Wasser.The mixture was then heated for 3 hours with stirring at 60 to 70 0, diluted after cooling with 100 parts of alcohol, filtered and washed with alcohol possibly also with water.
Das Chlorierungsprodukt läßt sich aus Nitrobenzol in braunroten Nädelchen kristallisieren und ist in Wasser und Alkalien unlöslich, in Schwefelsäure (6o° Be.) tiefblau löslich, in Oleum (23 Proz.) trübe blau löslich, in Eisessig heiß, schwer gelb löslich.The chlorination product can be crystallized from nitrobenzene in brown-red needles and is insoluble in water and alkalis, deep blue in sulfuric acid (60 ° Be.) soluble, in oleum (23 per cent.) cloudy blue soluble, in glacial acetic acid hot, poorly soluble in yellow.
Analog verfährt man bei Verwendung der freien Halogene.The same procedure is used when using the free halogens.
10 Teile des Produkts, erhalten nach Beispiel I bis 4 der Patentschrift 175067, werden innig mit 100 Teilen Nitrobenzol vermischt, darauf leitet man bei gewöhnlicher Temperatur während Y2 bis 3/4 Stunde langsam Chlor ein. Die braungelbe Farbe der Flüssigkeit schlägt nach Orangerot um. Man verdünnt mit 100 Teilen Alkohol, filtriert, wäscht mit Alkohol und eventuell noch mit Wasser aus.10 parts of the product obtained according to Example I to 4 of the patent specification 175067, are intimately mixed with 100 parts of nitrobenzene, it is at ordinary temperature for 2 to 3 Y / 4 hours slowly initiates chlorine. The brown-yellow color of the liquid changes to orange-red. It is diluted with 100 parts of alcohol, filtered, washed with alcohol and possibly with water.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE186596C true DE186596C (en) |
Family
ID=450345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT186596D Active DE186596C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE186596C (en) |
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0
- DE DENDAT186596D patent/DE186596C/de active Active
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