CH224873A - Process for the preparation of a chromable dye of the triarylmethane series. - Google Patents
Process for the preparation of a chromable dye of the triarylmethane series.Info
- Publication number
- CH224873A CH224873A CH224873DA CH224873A CH 224873 A CH224873 A CH 224873A CH 224873D A CH224873D A CH 224873DA CH 224873 A CH224873 A CH 224873A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- chromable
- preparation
- water
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000975 dye Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- TVKZDKSHNITMRZ-UHFFFAOYSA-N 3-(ethylamino)phenol Chemical compound CCNC1=CC=CC(O)=C1 TVKZDKSHNITMRZ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ALTIBIYWDZVHMD-UHFFFAOYSA-N [Na].ClC(C)S(=O)(=O)O Chemical compound [Na].ClC(C)S(=O)(=O)O ALTIBIYWDZVHMD-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 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
- 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
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
-
- 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
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
- C09B11/245—Phthaleins having both OH and amino substituent(s) on aryl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zurr Hauptpatent Nr. 198713. Verfahren zur Darstellung eines chromierbaren Farbstoffes der Triarylmethanreihe. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines chromierbaren Farbstoffes der Triarylmethan- reihe, welches dadurch gekennzeichnet ist, dass man Äthyl-p-sulfäthylamino-m-phenol mit 5-Bromtrimellithsäureanhydrid kondensiert und dann in Gegenwart von Wasser das Bromatom gegen die Hydroxylgruppe aus tauscht.
Der so erhaltene Farbstoff stellt ein rotes Pulver dar; er ist leicht in Wasser löslich und färbt die tierische Faser aus saurem Bade in gelbroten Tönen. Durch Nachchro- mieren wird der Farbton etwas rotstickiger. Beispiel: 26 Gewichtsteile Äthyl-p-sulfäthylamino- m-phenol (erhältlich z. B. durch Umsetzung von m-Äthylaminophenol mit @-chloräthan- sulfonsaurem Natrium in Wasser), 82 Ge wichtsteile 5-Bromtrimellithsäureanhydrid und 15 Gewichtsteile Chlorzink werden einige Stunden, z.
B. vier Stunden, bei 225 C unter Rühren erhitzt. Die erkaltete und fein pul verisierte Schmelze wird mehrmals mit je 200 Gewichtsteilen Äthylalkohol kalt verrührt, wobei der reine Farbstoff zurückbleibt.
Um das Bromatom gegen die Ilydroxyl- gruppe auszutauschen, werden 7,8 Gewichts teile des so erhaltenen Farbstoffes in etwa 5 /oigem wässrigem Piperidin unter Zusatz von je einem Gewichtsteil gupferchlorür und Kupferpulver im Autoklaven mehrere Stunden, z. B. fünf Stunden, auf 145-1501 C erhitzt. Die filtrierte Lösung wird eingedampft und im Vakuum bei 100 C getrocknet.
Der so erhaltene Farbstoff stellt ein rotes Pulver dar, ist leicht in Wasser löslich und färbt die tie rische Faser aus saurem Bade in gelbrotem Ton. Nachchromiert wird der Farbton etwas rotstickiger; die Echtheitseigenschaften sind sehr gut.
Additional patent to main patent no. 198713. Process for the preparation of a chromable dye of the triarylmethane series. The subject of the present additional patent is a process for the preparation of a chromable dye of the triarylmethane series, which is characterized in that ethyl-p-sulfäthylamino-m-phenol is condensed with 5-bromotrimellitic anhydride and then the bromine atom against the hydroxyl group in the presence of water exchanges.
The dye thus obtained is a red powder; it is easily soluble in water and colors the animal fibers from acid baths in yellow-red shades. After chrome plating, the color becomes a little redder. Example: 26 parts by weight of ethyl-p-sulfäthylamino-m-phenol (obtainable e.g. by reacting m-ethylaminophenol with sodium chloroethane sulfonic acid in water), 82 parts by weight of 5-bromotrimellitic anhydride and 15 parts by weight of zinc chloride are required for a few hours, z.
B. four hours, heated at 225 C with stirring. The cooled and finely pulverized melt is stirred several times with 200 parts by weight of ethyl alcohol each time, leaving the pure dye behind.
In order to exchange the bromine atom for the Ilydroxyl- group, 7.8 parts by weight of the dye thus obtained in about 5 /% aqueous piperidine with the addition of one part by weight of gupferchlorür and copper powder in the autoclave for several hours, for. B. five hours, heated to 145-1501 C. The filtered solution is evaporated and dried at 100 ° C. in vacuo.
The dye thus obtained is a red powder, is easily soluble in water and dyes the animal fiber from acid bath in a yellow-red tone. After chrome-plating, the color becomes a bit redder; the fastness properties are very good.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE241237X | 1937-12-24 | ||
| CH198713T | 1938-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224873A true CH224873A (en) | 1942-12-15 |
Family
ID=25723168
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224872D CH224872A (en) | 1937-12-24 | 1938-12-20 | Process for the preparation of a chromable dye of the triarylmethane series. |
| CH224873D CH224873A (en) | 1937-12-24 | 1938-12-20 | Process for the preparation of a chromable dye of the triarylmethane series. |
| CH224871D CH224871A (en) | 1937-12-24 | 1938-12-20 | Process for the preparation of a chromable dye of the triarylmethane series. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224872D CH224872A (en) | 1937-12-24 | 1938-12-20 | Process for the preparation of a chromable dye of the triarylmethane series. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224871D CH224871A (en) | 1937-12-24 | 1938-12-20 | Process for the preparation of a chromable dye of the triarylmethane series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (3) | CH224872A (en) |
-
1938
- 1938-12-20 CH CH224872D patent/CH224872A/en unknown
- 1938-12-20 CH CH224873D patent/CH224873A/en unknown
- 1938-12-20 CH CH224871D patent/CH224871A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH224871A (en) | 1942-12-15 |
| CH224872A (en) | 1942-12-15 |
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