DE267523C - - Google Patents
Info
- Publication number
- DE267523C DE267523C DENDAT267523D DE267523DA DE267523C DE 267523 C DE267523 C DE 267523C DE NDAT267523 D DENDAT267523 D DE NDAT267523D DE 267523D A DE267523D A DE 267523DA DE 267523 C DE267523 C DE 267523C
- Authority
- DE
- Germany
- Prior art keywords
- class
- yellow
- benzal chloride
- sulfur
- parts
- 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
- BEQBQOAWTXSRIB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-thiazole Chemical class C1=CSC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BEQBQOAWTXSRIB-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 241000131971 Bradyrhizobiaceae Species 0.000 claims 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- XEMRAKSQROQPBR-UHFFFAOYSA-N Benzotrichloride Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 3
- 229940095076 benzaldehyde Drugs 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-Dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical class C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229940117389 Dichlorobenzene Drugs 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
- 150000007979 thiazole derivatives Chemical class 0.000 description 2
- NINIDFKCEFEMDL-AKLPVKDBSA-N (35)S Chemical compound [35S] NINIDFKCEFEMDL-AKLPVKDBSA-N 0.000 description 1
- -1 6-dibenzoylaminoanthraquinone Chemical compound 0.000 description 1
- 241000490025 Schefflera digitata Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Description
In dem Patent 264943 ist ein Verfahren zur Darstellung von Anthrachinonthiazolen beschrieben, dadurch gekennzeichnet, daß man 2-Aminoanthrachinone oder deren Derivate, bei denen eine o-Stellung neben der oder den Aminogruppen frei ist, mit Benzotrichlorid oder dessen Derivaten boi Gegenwart von Schwefel oder schwefelabgebenden Substanzen erhitzt. 'In patent 264943 is a method for the preparation of anthraquinone thiazoles described, characterized in that 2-aminoanthraquinones or their derivatives, in which an o-position next to the amino group or groups is free, with benzotrichloride or its derivatives in the presence of sulfur or sulfur-releasing substances heated. '
Es wurde nun gefunden, daß man zu Thiazolderivaten des Anthrachinone in guter Ausbeute und Reinheit auch gelangt, wenn man das Benzotrichlorid durch Benzalchlorid ersetzt.It has now been found that thiazole derivatives of anthraquinones can be used in good Yield and purity can also be achieved if the benzotrichloride is replaced by benzal chloride replaced.
600 Teile Benzalchlorid, 100 Teile 2 · 6-Diäminoanthrachinon, 100 Teile Schwefel werden etwa 6 Stunden zum Sieden erhitzt. Dann wird mit 80.0 Teilen Dichlorbenzol verdünnt und nach. dem Erkalten das schön kristallinische Thiazolderivat abgesaugt, mit Dichlorbenzol und Alkohol gewaschen und getrocknet. Es färbt Baumwolle aus der Hydrosulfitküpe in sehr kräftigen, gelben, hervorragend echten Tönen an.600 parts of benzal chloride, 100 parts of 2 6-diäminoanthraquinone, 100 parts of sulfur are heated to the boil for about 6 hours. Then it is diluted with 80.0 parts of dichlorobenzene and after. the nicely crystalline thiazole derivative sucked off after cooling, with dichlorobenzene and alcohol washed and dried. It dyes cotton from the hydrosulfite vat in very strong, yellow, exceptionally real tones.
Analog verfährt man bei Verwendung anderer 2-Aminoanthrachinone. Die erhaltenen Anthrachinonthiazole bilden schöne, reine, gelbe Kristallpulver. Sie lösen sich in Schwefel-35 The same procedure is used when using other 2-aminoanthraquinones. The received Anthraquinone thiazoles form beautiful, pure, yellow crystal powders. They dissolve in sulfur-35
säure unverändert mit gelber Farbe. In Wasser und verdünnten Alkalien sind sie unlöslich. Aus hochsiedenden organischen Lösungsmitteln oder aus mäßig verdünnter Schwefelsäure lassen sie sich Umkristallisieren. Die Hydrosulfitküpen sind bläulichrot bis violett gefärbt, die Ausfärbungen auf Baumwolle gelb bis orangegelb.acidity unchanged with yellow color. They are insoluble in water and dilute alkalis. They can be recrystallized from high-boiling organic solvents or from moderately dilute sulfuric acid. The hydrosulfite vats are bluish-red to purple in color, the colors on cotton yellow to orange-yellow.
Ersetzt man im vorstehenden Beispiel das Benzalchlorid durch Benzaldehyd, so gelangt man zu einem vollständig anderen Ergebnis; man erhält nämlich lediglich 2 · 6-Dibenzoylaminoanthrachinon. Mit Rücksicht auf dieses Verhalten des Benzaldehyds, welches nach den Angaben der Patentschriften 229165, Kl. 22, 232711, Kl. 22, 232712, Kl. 22, und 235051, Kl. 12, nicht zu erwarten war, ist der Reaktionsverlauf bei Verwendung von Benzalchlorid gemäß vorliegendem Verfahren durchaus überraschend, zumal aus der Patentschrift 247246, Kl. 22, zu schließen war, daß Benzalchlorid und Benzaldehyd zu den gleichen Produkten führen würden.If, in the above example, the benzal chloride is replaced by benzaldehyde, then the result is obtained one to a completely different result; namely, only 2 · 6-dibenzoylaminoanthraquinone is obtained. With regard to this behavior of benzaldehyde, which according to the information in patents 229165, class 22, 232711, class 22, 232712, class 22, and 235051, Class 12, which was not to be expected, is the course of the reaction when using benzal chloride according to the present method quite surprising, especially from patent specification 247246, Cl. 22, it was concluded that benzal chloride and benzaldehyde are the same products would lead.
Pate ν τ-An s PRU ch:Pate ν τ-An s PRU ch:
5555
Abänderung des Verfahrens des Patents 264943, dadurch gekennzeichnet, daß man an Stelle von Benzotrichlorid Benzalchlorid verwendet.Modification of the method of patent 264943, characterized in that one benzal chloride used in place of benzotrichloride.
BERLIN. GEDRUCKT IN DER REICHSDRUCKEREI.BERLIN. PRINTED IN THE REICHSDRUCKEREI.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE267523C true DE267523C (en) |
Family
ID=524571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT267523D Active DE267523C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE267523C (en) |
-
0
- DE DENDAT267523D patent/DE267523C/de active Active
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