CH107209A - Process for the preparation of a vat dye of the dibenzanthrone series. - Google Patents
Process for the preparation of a vat dye of the dibenzanthrone series.Info
- Publication number
- CH107209A CH107209A CH107209DA CH107209A CH 107209 A CH107209 A CH 107209A CH 107209D A CH107209D A CH 107209DA CH 107209 A CH107209 A CH 107209A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- vat dye
- dye
- oxydibenzanthrone
- dibenzanthrone
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 4
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- JOOGLLGUPPDXCL-UHFFFAOYSA-N 1-(7-oxobenzo[a]phenalen-1-yl)oxybenzo[b]phenalen-7-one Chemical compound C1(=CC=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23)OC2=CC=C3C=CC=C1C(=O)C4=CC=CC=C4C2=C31 JOOGLLGUPPDXCL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NWRRLJGMPCIDEU-UHFFFAOYSA-N (6-methoxynaphthalen-1-yl)-phenylmethanone Chemical compound COC=1C=C2C=CC=C(C2=CC1)C(C1=CC=CC=C1)=O NWRRLJGMPCIDEU-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/22—Dibenzanthrones; Isodibenzanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Küpenfarbstoffes der Dibenzanthronreihe. Nach den Angaben von Scholl und Seer (Annalen 394, Seite 126, Fussnote 1 und Seite 154) lassen sich hydroxylierte Benzan- throne nicht durch schmelzendes Alkali in Küpenfarbstoffe, d. h. in Dibenzanthronderivate, überführen.
Es wurde nun gefunden, dass überraschen derweise das Oxybenzanthron, welches durch Verbacken von 6-Methoxy-l-benzoylnaphtalin mit Aluminiumchlorid erhalten werden kann, bei der Alkalischmelze ein Oxydibenzanthron liefert, und dass durch Einführung des Methyl- restes in die Oxygruppe dieses Oxydibenzan- throns ein neuer Farbstoff entsteht, welcher sich durch hervorragende Echtheitseigen schaften auszeichnet.
Es war nicht voraus zusehen, dass dieses Oxydibenzanthron sich alkylieren lassen würde; da zum Beispiel durch die Arbeiten von Perkin Journ. Chem. Soc. 121 Seite 476 ff. Oxybenzanthrone be kannt geworden sind, welche Oxygruppen enthalten, in denen das Hydroxylwasserstoff- atom nicht oder nur sehr schwer durch an dere Reste ersetzt werden kann.
<I>_ Beispiel:</I> 1n ein geschmolzenes Gemisch von 100 Teilen Ätzkali und 10 Teilen alkoholischem Kali trägt man bei 180 unter Rühren 20 Teile des durch Verbacken von 6-Methoxy-l-ben- zoylnaphtalin mittelst Aluminiumchlorid er hältlichen Oxybenzanthrons ein. Allmählich steigert man die Temperatur bis auf etwa 230" und erhitzt noch 1j4 Stunde lang.
Der abgeschiedene Farbstoff wird vom geschmol zenen Kali abgetrennt, mit Wasser unter gleichzeitigem Durchleiten von Luft gekocht und nach dem Ansäuern mit Salzsäure äb- gesaugt. Getrocknet stellt das Reaktions produkt ein schwärzliches Pulver dar. Mit alkalischer Hydrosulfitlösung liefert es eine blaue Küpe, aus der Baumwolle in olive- farbenen Tönen angefärbt wird, die beim An säuern nach Blau umschlagen.
10 Teile des so erhaltenen Dioxydibenzan- throns werden mit 10 Teilen Toluolsulfo- säuremethylester und 5 Teilen trockener Soda in Nitrobenzollösung 5 Stunden auf 180-190 erhitzt. Nach dem Erkalten verdünnt man mit Sprit, saugt ab und wäscht mit Sprit nach. Durch Auskochen mit verdünnter Salz säure wird der Farbstoff von Verunreinigungen befreit. Er stellt getrocknet ein grünschwar zes Pulver dar und färbt aus blauer Küpe Baumwolle in echten. blaugrünen Tönen.
Process for the preparation of a vat dye of the dibenzanthrone series. According to the information provided by Scholl and Seer (Annalen 394, page 126, footnote 1 and page 154), hydroxylated benzan thrones cannot be converted into vat dyes by melting alkali. H. in dibenzanthrone derivatives.
It has now been found that, surprisingly, the oxybenzanthrone, which can be obtained by baking 6-methoxy-l-benzoylnaphthalene with aluminum chloride, delivers an oxydibenzanthrone when the alkali melts, and that by introducing the methyl radical into the oxy group of this oxydibenzanthrone a new dye is created, which is characterized by excellent fastness properties.
It was not foreseeable that this oxydibenzanthrone would be alkylated; for example through the work of Perkin Journ. Chem. Soc. 121 page 476 ff. Oxybenzanthrones have become known which contain oxy groups in which the hydroxyl hydrogen atom cannot be replaced, or only with great difficulty, by other residues.
<I> _ Example: </I> In a molten mixture of 100 parts of caustic potash and 10 parts of alcoholic potash, 20 parts of the oxybenzanthrone obtainable by baking 6-methoxy-1-benzoylnaphthalene with aluminum chloride are introduced at 180 with stirring . Gradually increase the temperature to about 230 "and heat for a further 14 hours.
The deposited dye is separated from the molten potash, boiled with water while air is passed through and, after acidification, sucked off with hydrochloric acid. When dried, the reaction product is a blackish powder. With an alkaline hydrosulphite solution, it provides a blue vat from which cotton is dyed in olive-colored tones that turn blue when acidified.
10 parts of the dioxydibenzanthrone thus obtained are heated to 180-190 for 5 hours with 10 parts of methyl toluenesulfate and 5 parts of dry soda in nitrobenzene solution. After cooling, it is diluted with fuel, suctioned off and washed with fuel. The dye is freed from impurities by boiling with dilute hydrochloric acid. When dried, it is a greenish-black powder and dyes real cotton from a blue vat. blue-green tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH107209T | 1924-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH107209A true CH107209A (en) | 1924-10-01 |
Family
ID=4366120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH107209D CH107209A (en) | 1924-02-18 | 1924-02-18 | Process for the preparation of a vat dye of the dibenzanthrone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH107209A (en) |
-
1924
- 1924-02-18 CH CH107209D patent/CH107209A/en unknown
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