DE273340C - - Google Patents
Info
- Publication number
- DE273340C DE273340C DENDAT273340D DE273340DA DE273340C DE 273340 C DE273340 C DE 273340C DE NDAT273340 D DENDAT273340 D DE NDAT273340D DE 273340D A DE273340D A DE 273340DA DE 273340 C DE273340 C DE 273340C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- sulfur
- aminoacetophenone
- indigo
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- GTDQGKWDWVUKTI-UHFFFAOYSA-N 1-(2-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 claims description 3
- 229940097275 Indigo Drugs 0.000 claims description 3
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 240000007871 Indigofera tinctoria Species 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001062009 Indigofera Species 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-Aminoacetophenone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring 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
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 273340 KLASSE 22 e. GRUPPE- M 273340 CLASS 22 e. GROUP
Patentiert im Deutschen Reiche vom 11. Juni 1913 ab.Patented in the German Empire on June 11, 1913.
Es wurde gefunden, daß man das o-Aminoacetophenon sowie dessen Homologe und Substitutionsprodukte durch Erhitzen mit Schwefel in die zugehörigen Indigofarbstoffe umwandeln kann. Das Verfahren kann ohne oder mit Anwendung von Lösungs- bzw. Verdünnungsmitteln ausgeführt werden; als solche eignen sich z. B. hochsiedende Kohlenwasserstoffe, Naphta, Chinolin und andere. Die erforderliehen Aminoacetophenone sind nach bekannten Methoden, insbesondere nach dem Verfahren der Patentschrift 56971, leicht erhältlich.It has been found that o-aminoacetophenone and its homologues and substitution products can be used can convert into the associated indigo dyes by heating with sulfur. The procedure can be with or without Use of solvents or diluents are carried out; suitable as such z. B. high-boiling hydrocarbons, naphtha, quinoline and others. The required Aminoacetophenones are easily obtainable by known methods, in particular by the process of patent specification 56971.
!5 i. Indigo. 50 Gewichtsteile o-Aminoacetophenon werden mit etwa 25 Gewichtsteilen Schwefel im Ölbade unter Umrühren auf 210 bis 2300 (Temperatur des Ölbades) erhitzt. Die Reaktion ist beendet, sobald die Schwefelwasserstoffentwicklung aufgehört hat. Der gebildete Indigo wird zweckmäßig durch Extraktion mit Schwefelkohlenstoff oder durch Umküpen gereinigt.! 5 i. Indigo. 50 parts by weight of o-aminoacetophenone are heated with about 25 parts by weight of sulfur in an oil bath with stirring to 210 to 230 0 (temperature of the oil bath). The reaction is complete as soon as the evolution of hydrogen sulfide has ceased. The indigo formed is expediently purified by extraction with carbon disulfide or by evaporation.
2. Dibromindigo. 100 Gewichtsteile 5-Brom-2-aminoacetophenon (Berichte XVII, 965), gelöst in etwa 200 Teilen Chinolin, werden mit 30 Gewichtsteilen Schwefel in der im vorigen Beispiel beschriebenen Weise erhitzt. Der erhaltene Dibromindigo wird mit Chinolin gewaschen und mit verdünnter Salzsäure ausgekocht. 2. Dibromoindigo. 100 parts by weight of 5-bromo-2-aminoacetophenone (Reports XVII, 965), dissolved in about 200 parts of quinoline, are used with 30 parts by weight of sulfur heated in the manner described in the previous example. Of the The dibromoindigo obtained is washed with quinoline and boiled with dilute hydrochloric acid.
3. ß-Naphtindigo. 20 Gewichtsteile 2-Aminoi-acetonaphton (Patentschrift 56971) werden mit etwa 7 Teilen Schwefel in der oben beschriebenen Weise erhitzt. Der erhaltene Farbstoff ist identisch mit dem ß-Naphtindigo von Wichelhaus (Berichte XXVI, 2547).3. β-naphthindigo. 20 parts by weight of 2-aminoacetonaphton (Patent 56971) are with about 7 parts of sulfur in the above Way heated. The dye obtained is identical to the ß-naphtindigo of Wichelhaus (Reports XXVI, 2547).
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE273340C true DE273340C (en) |
Family
ID=529802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT273340D Active DE273340C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE273340C (en) |
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0
- DE DENDAT273340D patent/DE273340C/de active Active
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