CH215845A - Process for the preparation of a basic triphenylmethane dye. - Google Patents
Process for the preparation of a basic triphenylmethane dye.Info
- Publication number
- CH215845A CH215845A CH215845DA CH215845A CH 215845 A CH215845 A CH 215845A CH 215845D A CH215845D A CH 215845DA CH 215845 A CH215845 A CH 215845A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- triphenylmethane dye
- carried out
- basic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- -1 ice peroxide Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LAMTXWQPHWUMLX-UHFFFAOYSA-N n-butan-2-ylaniline Chemical compound CCC(C)NC1=CC=CC=C1 LAMTXWQPHWUMLX-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 211928. Verfahren zur Herstellung eines basischen Triphenylmethanfarbstoffes. Gegenstand vorliegender Erfindung ist die Herstellung eines neuen basischen Tri- rhenylmethanfarbstoffes, durch Kondensation von Oxäthyl-sek.-butylanilin mit o-Chlor- benzaldehyd und anschliessende Oxydation der gebildeten Leukoverbindung. Die Kon densation kann in Gegenwart von Salzsäure, die Oxydation mit Hilfe von Bl-eisuperoxyd durchgeführt werden.
Der erhältliche Farb stoff färbt gebeizte Baumwolle in blaustichig grünen Tönen an.
<I>Beispiel:</I> 20 Teile Oxäthyl-,sek.-butylanilin und 7 Teile o-Chlorbenzaldehyd werden mit 3 Tei len Wasser und 6 Teilen Schwefelsäure von 60 B6 bis zur beendigten Kondensation un ter Rühren auf 103 erhitzt. Nach Verdün nung mit Wasser und gegebenenfalls Destil lieren mit Wasserdampf zur Vertreibung von Resten überschüssiger Base oder Aldehyd er- hält man die Leukoverbindung, die nach Um kristallisieren aus 1Vlethylalkohol den Schmelz punkt 115 hat.
Nach Oxydation mit Schwefelsäure und 131eisuperoxyd gewinnt man durch Aussahen mit Natriumsulfat den Farbstoff als rot bronzierendes Harz, welcher ,die gebeizte Fa ser in blaustichig grünen Tönen von grösse rer Klarheit anfärbt als der bekannte Farb stoff aus o-Chlorbenzaldehyd und Dimethyl- anilin. Der Farbstoff zeigt eine bessere Lös lichkeit als der isomere Farbstoff aus nor- malprimär-Butylaniaäin.
Additional patent to main patent no. 211928. Process for the production of a basic triphenylmethane dye. The present invention relates to the preparation of a new basic tri-rhenylmethane dye by condensation of oxethyl-sec-butylaniline with o-chlorobenzaldehyde and subsequent oxidation of the leuco compound formed. The condensation can be carried out in the presence of hydrochloric acid and the oxidation can be carried out with the aid of Bl-eisperoxid.
The available dye stains stained cotton in bluish green tones.
<I> Example: </I> 20 parts of oxethyl-, sec-butylaniline and 7 parts of o-chlorobenzaldehyde are heated to 103 with 3 parts of water and 6 parts of sulfuric acid of 60 B6 until the condensation is complete. After dilution with water and, if necessary, distillation with steam to drive off residues of excess base or aldehyde, the leuco compound is obtained, which has a melting point of 115 after recrystallization from 1Vlethyl alcohol.
After oxidation with sulfuric acid and ice peroxide, the dye is obtained as a red bronzing resin by peeling with sodium sulfate, which stains the stained fiber in bluish green tones of greater clarity than the known dye made from o-chlorobenzaldehyde and dimethyl aniline. The dye shows better solubility than the isomeric dye made from normal primary butyl anaenine.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE215845X | 1938-03-28 | ||
| CH211928T | 1939-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215845A true CH215845A (en) | 1941-07-15 |
Family
ID=25725125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215845D CH215845A (en) | 1938-03-28 | 1939-03-22 | Process for the preparation of a basic triphenylmethane dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215845A (en) |
-
1939
- 1939-03-22 CH CH215845D patent/CH215845A/en unknown
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