DE14621C - Process for the preparation of violet, blue and green dyes by means of trichloromethyl sulfochloride and the use of trichloromethyl sulfochloride for the oxidation of leuco compounds - Google Patents
Process for the preparation of violet, blue and green dyes by means of trichloromethyl sulfochloride and the use of trichloromethyl sulfochloride for the oxidation of leuco compoundsInfo
- Publication number
- DE14621C DE14621C DENDAT14621D DE14621DA DE14621C DE 14621 C DE14621 C DE 14621C DE NDAT14621 D DENDAT14621 D DE NDAT14621D DE 14621D A DE14621D A DE 14621DA DE 14621 C DE14621 C DE 14621C
- Authority
- DE
- Germany
- Prior art keywords
- sulfochloride
- trichloromethyl
- preparation
- oxidation
- blue
- 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
- RYFZYYUIAZYQLC-UHFFFAOYSA-N Perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 title description 3
- 239000001046 green dye Substances 0.000 title description 2
- 230000003647 oxidation Effects 0.000 title description 2
- 238000007254 oxidation reaction Methods 0.000 title description 2
- 239000001045 blue dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 7
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 150000003336 secondary aromatic amines Chemical class 0.000 claims 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DYFFAVRFJWYYQO-UHFFFAOYSA-N N-methyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- ISGXOWLMGOPVPB-UHFFFAOYSA-N N,N-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- FKJARBPQBIATJT-UHFFFAOYSA-N N-benzyl-N-phenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
- OETTVJDNCACMPC-UHFFFAOYSA-N N-pentyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCC)C1=CC=CC=C1 OETTVJDNCACMPC-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000001047 purple dye Substances 0.000 description 1
- 239000002966 varnish Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
zur Oxydation von Leukoverbindungen.for the oxidation of leuco compounds.
Patentirt im Deutschen Reiche vom 28. December 1880 ab.Patented in the German Empire on December 28, 1880.
ι Theil Methyldiphenylamin, 1 bis 2 Theile Trichlormethylsulfochlorid (C Cl3 .S O2 Cl), welches man aus Schwefelkohlenstoff, Braunstein und Salzsäure dargestellt hat, mischt man mit 5 Theilen Kochsalz innig und erhitzt es allmälig bis auf 1100C. Es entsteht eine kupferfarbene Schmelze, welche man nach einander mit Wasser, Alkali und concentrirter Salzsäure behandelt, um die unangegriffenen Producte zu entfernen. Die unlösliche Farbbase wird mittelst Schwefelsäure in ein in Wasser lösliches Product verwandelt und wie gewöhnlich weiter verarbeitet. Der Farbstoff färbt Wolle und Seide direct grünstichig blau.ι part of methyldiphenylamine, 1 to 2 parts of trichloromethylsulfochloride (C Cl 3 .SO 2 Cl), which has been prepared from carbon disulfide, manganese dioxide and hydrochloric acid, is mixed intimately with 5 parts of table salt and heated gradually up to 110 ° C. A copper-colored melt, which is treated successively with water, alkali, and concentrated hydrochloric acid, in order to remove the unaffected products. The insoluble color base is converted into a water-soluble product by means of sulfuric acid and further processed as usual. The dye directly dyes wool and silk with a greenish blue.
Das Methyldiphenylamin kann ersetzt werden durch das Aethyl- oder Amyldiphenylamin.The methyldiphenylamine can be replaced by the ethyl or amyldiphenylamine.
Wendet man statt des Methyldiphenylamin Benzyldiphenylamin oder Dibenzylphenylamin an, so erhält man grüne Farbstoffe, welche in Alkohol löslich sind. Durch Ueberführen in ihre Sulfosäuren werden dieselben in eine in Wasser lösliche Form gebracht.If you use benzyldiphenylamine or dibenzylphenylamine instead of methyldiphenylamine, this gives green dyes which are soluble in alcohol. By converting into theirs Sulphonic acids are made into a water-soluble form.
Ersetzt man das Methyldiphenylamin durch Diphenylamin oder Dimethylanilin, so erhält man violette Farbstoffe. Nur der mittelst Dimethylanilin dargestellte Farbstoff ist direct in Wasser löslich, während sonst nur die Sulfosäuren des mittelst Diphenylamin dargestellten Farbstoffes wasserlöslich sind.If the methyldiphenylamine is replaced by diphenylamine or dimethylaniline, so is obtained one purple dyes. Only the dye prepared by means of dimethylaniline is direct in Soluble in water, while otherwise only the sulfonic acids of diphenylamine are represented Dye are soluble in water.
Behufs Oydation von Leukobasen mit Trichlormethylsulfochlorid mischt man ζ. Β. ι Theil desselben innig mit 1 Theil Tetramethyldiamidotriphenylmethan und 5 Theilen Kochsalz und erhitzt langsam bis auf 1 io°. Die Schmelze wird mit Wasser gekocht und mit Alkalilösung behandelt.To oxidize leuco bases with trichloromethyl sulfochloride, mix ζ. Β. ι part the same intimately with 1 part tetramethyldiamidotriphenylmethane and 5 parts common salt and slowly heats up to 1 10 °. The melt is boiled with water and with alkali solution treated.
Die so erhaltene Farbstoffbase wird nach bekannter Art weiter verarbeitet.The dye base obtained in this way is processed further in a known manner.
Statt der Leukoverbindungen kann man auch deren Sulfosäuren anwenden.Instead of the leuco compounds, their sulfonic acids can also be used.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE14621C true DE14621C (en) |
Family
ID=291700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT14621D Active DE14621C (en) | Process for the preparation of violet, blue and green dyes by means of trichloromethyl sulfochloride and the use of trichloromethyl sulfochloride for the oxidation of leuco compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE14621C (en) |
-
0
- DE DENDAT14621D patent/DE14621C/en active Active
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