DE261737C - - Google Patents
Info
- Publication number
- DE261737C DE261737C DENDAT261737D DE261737DA DE261737C DE 261737 C DE261737 C DE 261737C DE NDAT261737 D DENDAT261737 D DE NDAT261737D DE 261737D A DE261737D A DE 261737DA DE 261737 C DE261737 C DE 261737C
- Authority
- DE
- Germany
- Prior art keywords
- diaminoanthraquinone
- derivatives
- parts
- anthraquinone
- sulfuric acid
- 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
- 239000007859 condensation product Substances 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 claims 1
- -1 anthraquinone aldehydes Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- IWRVPXDHSLTIOC-UHFFFAOYSA-N 4-phenyldiazenylbenzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 IWRVPXDHSLTIOC-UHFFFAOYSA-N 0.000 description 1
- XBWFYFHSIFEXMY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbaldehyde Chemical compound C1=CC=C2C(=O)C3=CC(C=O)=CC=C3C(=O)C2=C1 XBWFYFHSIFEXMY-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- UQOGMMRJGCDYMB-UHFFFAOYSA-N anthracene-9,10-dione;hydride Chemical class [H-].C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 UQOGMMRJGCDYMB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
;.■- M 261737'-KLASSE 22 ö. GRUPPE ;. ■ - M 261737'-CLASS 22 ö. GROUP
Patentiert im Deutschen Reiche vom 10. Juni 1911 ab.Patented in the German Empire on June 10, 1911.
Es wurde die Beobachtung gemacht, daß man durch Einwirkung von cu-Dichlormethylanthrachinon bzw. Anthrachinonaldehyden oder deren Derivaten auf o-Diaminoanthrachinone, wie ι · 2- und 2 · 3-Diaminoanthrachinon, bei Temperaturen unter 120° zu neuen Kondensationsprodukten gelangt, welche ausgesprochenen Küpenfarbstoffcharakter besitzen. Die neuen Produkte sind verschieden von den bei höheren Temperaturen entstehenden Verbindungen. Sie stehen anscheinend zu diesen im Verhältnis einer DihydrOverbindung eines Imidazole zu diesem selbst. Dies wird dadurch wahrscheinlich, daß sie beim Behandein mit oxydierenden Mitteln, wie Schwefelsäure und Persulfat oder Brom in Eisessig, oder durch Erhitzen in Nitrobenzol in die durch Kondensation bei höheren Temperaturen erhältlichen Verbindungen übergehen.The observation was made that the action of cu-dichloromethylanthraquinone or anthraquinone hydrides or their derivatives to o-diaminoanthraquinones, like ι · 2- and 2 · 3-diaminoanthraquinone, at temperatures below 120 ° to new condensation products which have a pronounced vat dye character. The new products are different from the at compounds formed at higher temperatures. You apparently stand by these im Ratio of a dihydric compound of an imidazole to this itself likely to be caused by treatment with oxidizing agents such as sulfuric acid and persulfate or bromine in glacial acetic acid, or by heating in nitrobenzene into the by condensation at higher temperatures available connections.
10 Teile 1 · 2-Diaminoanthrachinon, 11 bis 14 Teile Anthrachinon-2-aldehyd, 200 Teile Pyridin werden so lange zum Sieden erhitzt, bis eine weitere Ausscheidung von Kristallen des Kondensationsprodukts nicht mehr stattfindet. Nach dem Absaugen des Kristallbreies und Waschen mit Alkohol erhält man den Farbstoff direkt in reiner Form; derselbe färbt Baumwolle in der alkalischen Hydrosulfitküpe in violetten Tönen an. Die Elementaranalyse ergab Zahlen, die auf die Formel10 parts of 1 x 2-diaminoanthraquinone, 11 to 14 parts of anthraquinone-2-aldehyde, 200 parts of pyridine are heated to the boil until until further precipitation of crystals of the condensation product no longer takes place. After filtering off the crystal pulp and washing with alcohol, the dye is obtained directly in pure form; same colors cotton in the alkaline hydrosulphite vat in violet tones. The elemental analysis yielded numbers based on the formula
NH-CHNH-CH
NHNH
5555
6060
stimmen; die Lösung in konzentrierter Schwefeisäure ist grünlichgelb.voices; the solution in concentrated sulfuric acid is greenish yellow.
Ersetzt man in vorliegendem Beispiel das ι · 2-Diaminoanthrachinon durch das isomere 2 • 3-Diaminoanthrachinon, so erhält man einen Baumwolle orange färbenden Küpenfarbstoff, der sich in konzentrierter Schwefelsäure mit gelber Farbe löst.If you replace that in the present example ι · 2-diaminoanthraquinone by the isomeric 2 • 3-diaminoanthraquinone, one obtains a Cotton orange coloring vat dye, which is contained in concentrated sulfuric acid yellow color dissolves.
Statt Pyridin können auch andere Lösungsmittel, wie Naphtalin, Nitrobenzol usw., verwendet werden. Man muß dann jedoch Sorge tragen, daß die Temperatur etwa 115 bis 120 °Instead of pyridine, other solvents, such as naphthalene, nitrobenzene, etc., can also be used. But then you have to worry bear that the temperature is about 115 to 120 °
nicht übersteigt, weil bei höherer Temperatur sich Farbstoffe anderer Art, vermutlich die entsprechenden Imidazole, bilden.does not exceed, because at a higher temperature dyes of a different kind, presumably the corresponding imidazoles.
io Teile ι · 2-Diaminoanthrachinon, 20 Teile ai-Dichlor-2-methylanthrachinon, 200 Teile Pyridin werden einige Zeit am Rückflußkühler gekocht, wobei sich ein dem in vorhergehendem Beispiel beschriebenen in Nuance sehr ähnlicher violetter Farbstoff ausscheidet.10 parts ι · 2-diaminoanthraquinone, 20 parts ai-dichloro-2-methylanthraquinone, 200 parts of pyridine are boiled for some time on the reflux condenser, where the in the previous Example described in shade very similar violet dye precipitates.
Ersetzt man das 1 · 2-Diaminoanthrachinon durch das isomere 2 · 3-Diaminoanthrachinon, so bildet sich unter den angegebenen Bedingungen ein aus der Hydrosulfitküpe in gelben Tönen färbendes Kondensationsprodukt, welches sich in konzentrierter Schwefelsäure mit roter Farbe löst.Replaces the 1 · 2-diaminoanthraquinone by the isomeric 2 · 3-diaminoanthraquinone, then forms under the specified conditions a condensation product which turns yellow from the hydrosulfite vat and which dissolves in concentrated sulfuric acid with a red color.
Analog kann man bei Verwendung anderer Aldehyde oder a-Halogenmethylderivate der Anthrachinonreihe verfahren.Analogously, when using other aldehydes or a-halomethyl derivatives, the Proceed with anthraquinone series.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE261737C true DE261737C (en) |
Family
ID=519271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT261737D Active DE261737C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE261737C (en) |
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