CH235466A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH235466A CH235466A CH235466DA CH235466A CH 235466 A CH235466 A CH 235466A CH 235466D A CH235466D A CH 235466DA CH 235466 A CH235466 A CH 235466A
- Authority
- CH
- Switzerland
- Prior art keywords
- vat
- production
- dye
- vat dye
- nitrobenzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000004992 toluidines Chemical class 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
- C09B5/26—Carbazoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 2'2'6452e. Verfahren zur Herstellung eines Küpenfarbstoffes. Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung eines Küpen- farbstoffes, das dadurch igekennzeichnet ist, dass man das Anthrimid der folgenden Formel
EMI0001.0008
mit carbazolierend wirkenden Mitteln be handelt.
Es empfiehlt sich, das Reaktions produkt mit oxydierend wirkenden Mitteln, wie Natriumnitrit, nachzubehandeln, um es in die dem Küpenfarbstoff entsprechende Oxydationsstufe zu überführen. Als carbazo- lierend wirkende Mittel kommen beispiels- weise Aluminiumchlorid in Nitrobenzol oder konzentrierte Schwefelsäure in Frage.
Der erhältliche Farbstoff ist in konzen trierter Schwefelsäure mit tiefblauer Farbe löslich. Er färbt Wolle aus der rotbraun ge färbten Küpe in kräftigem dunklem Khaki von sehr guten E,chth-eitseigens-chaften an.
Das als Ausgangsmaterial benutzte An thrimid der obenstehenden Formel kann nach bekannten Methoden durch Umsetzung von 1-Benzoylamino-4-toluido-5-chloranthra- chinon mit 1-Amino-5-benzoylaminoanthTa- chinon hergestellt werden.
Ersteres kann seinerseits hergestellt werden durch Behand lung des bekannten I - Nitro - 4.'5 -.dichlor - anthrachinons mit Toluidin unter Zusatz von wasserfreiem Natriumacetat, unter anschlie- ssend-er Reduzierung der Nitrogruppe und Benzoylierung der Aminogruppe. Beispiel:
5 Gewichtsteile des Anthrimids der oben stehenden Formel trägt man bei etwa 25 in eine Auflösung von 2'2 Gewichtsteilen wasserfreiem Aluminiumchlorids in 50 Cxe- iviehtsteile Nitrobenzol ein und erwärmt die Mischung ungefähr 1 Stunde auf 70 bis 80". Nach dem Abkühlen auf 30 setzt man 1,5 Gewichtsteile fein pulverisiertes Na triumnitrit zu und rührt die Mischung noch einige Zeit ohne weiteres Erwärmen.
Dann tvird unter Kühlung in überschüssige ver dünnte Natronlauge eingerührt und das Nitrobenzol mit Wasserdampf abgetrieben. Das gebildete Reaktionsprodukt kristallisiert aus Nitrobenzol in Nädelchen, die in konzen trierter Schwefelsäure tiefblau löslich sind. Auf Baumwolle erhält man aus kalter wie heisser rotbraun gefärbter Küpe ein kräftiges. dunkles Khaki von sehr guten Echtheits- eigenechaften.
Additional patent to main patent No. 2'2'6452e. Process for the production of a vat dye. The present invention relates to a process for the preparation of a vat dye which is characterized in that the anthrimide of the following formula is used
EMI0001.0008
with carbazolating agents.
It is advisable to post-treat the reaction product with oxidizing agents, such as sodium nitrite, in order to transfer it to the oxidation stage corresponding to the vat dye. Carbazolizing agents are, for example, aluminum chloride in nitrobenzene or concentrated sulfuric acid.
The available dye is soluble in concentrated sulfuric acid with a deep blue color. He dyes wool from the reddish-brown dyed vat in strong dark khaki with very good natural properties.
The anthrimide of the above formula used as the starting material can be prepared by known methods by reacting 1-benzoylamino-4-toluido-5-chloroanthraquinone with 1-amino-5-benzoylaminoanthtaquinone.
The former can in turn be prepared by treating the known I-nitro-4.'5 -.dichloro-anthraquinone with toluidine with addition of anhydrous sodium acetate, with subsequent reduction of the nitro group and benzoylation of the amino group. Example:
5 parts by weight of the anthrimide of the above formula are added at about 25 to a solution of 2'2 parts by weight of anhydrous aluminum chloride in 50 parts by weight of nitrobenzene, and the mixture is heated to 70 to 80 "for about 1 hour Add 1.5 parts by weight of finely powdered sodium nitrite and stir the mixture for some time without further heating.
Then it is stirred into excess dilute sodium hydroxide solution with cooling and the nitrobenzene is driven off with steam. The reaction product formed crystallizes from nitrobenzene in needles that are deep blue soluble in concentrated sulfuric acid. On cotton, a strong vat is obtained from a cold and hot red-brown colored vat. dark khaki with very good authenticity properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE235466X | 1939-12-27 | ||
| CH226452T | 1941-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235466A true CH235466A (en) | 1944-11-30 |
Family
ID=25726993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235466D CH235466A (en) | 1939-12-27 | 1941-07-08 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235466A (en) |
-
1941
- 1941-07-08 CH CH235466D patent/CH235466A/en unknown
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