DE63026C - Process for the preparation of green basic dyes of the triphenylmethane series - Google Patents
Process for the preparation of green basic dyes of the triphenylmethane seriesInfo
- Publication number
- DE63026C DE63026C DENDAT63026D DE63026DA DE63026C DE 63026 C DE63026 C DE 63026C DE NDAT63026 D DENDAT63026 D DE NDAT63026D DE 63026D A DE63026D A DE 63026DA DE 63026 C DE63026 C DE 63026C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- basic dyes
- dye
- green basic
- green
- 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.)
- Expired - Lifetime
Links
- 239000000981 basic dye Substances 0.000 title 1
- 150000004961 triphenylmethanes Chemical class 0.000 title 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 2-Nitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L Light Green SF yellowish Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- -1 ethyl compound Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMPATENTAM
/7J2 .CH-C6 H4 O) / 7J 2 .CH-C 6 H 4 O)
Durch Einwirkung von Chlordinitrobenzol (C/: IVO2 : NO2 =1:2:4) auf m-Amidotetraalkyldiamidotriphenylmethan erhält rrian Dinitrophenbl-m-amidotetraalkyldiamidotriphenylmethan. The action of chloronitrobenzene (C /: IVO 2 : NO 2 = 1: 2: 4) on m-amidotetraalkyldiamidotriphenylmethane gives dinitrophenbl-m-amidotetraalkyldiamidotriphenylmethane.
([CA8],, -N- C6H4J8 · CH- C6H,- NH2 + C6H3Cl(NO2J2 ([CA 8] ,, -N-C 6 H 4 · 8 J CH- C 6 H, - NH 2 + C 6 H 3 Cl (NO 2 J 2
= HCl([CH3I2 -N6 J = HCl ([CH 3 I 2 -N 6 J
NH-C6 H3(NO2),.NH-C 6 H 3 (NO 2 ) ,.
Durch Oxydation dieser Leukobase entsteht ein Farbstoff, der wegen seiner gelbgrünen Nuance werthvoll erscheint.Oxidation of this leuco base creates a dye, which because of its yellow-green Nuance appears valuable.
Obwohl der Körper ein basischer Triphenylmethanfarbstoff ist, läfst er sich auf thierische Faser in saurem Bade gerade so wie Säuregrün auffärben — der erste Fall dieser Art. Ferner soll der Farbstoff in der Lackfabrikation Verwendung finden, da seine -Nuance bisher nur durch Mischung von Farbstoffen erzielt werden konnte.Although the body is a basic triphenylmethane dye, it can be derived from animal ones Coloring fibers in an acid bath just like acid green - the first case of this kind. Furthermore, the dye is to be used in paint production, as its nuance has so far been used could only be achieved by mixing dyes.
Zur Darstellung des Körpers verfährt man wie folgt:One proceeds to represent the body as follows:
. Chlordinitrobenzol (1 kg) und m-Amidotetramethyldiamidotriphenylmethan (2 kg) werden in ungefähr 10 1 Alkohol gelöst und einige Stunden erwärmt. Hierauf wird der Alkohol abdestillirt, der Rückstand in verdünnter Schwefelsäure gelöst, die Base mit Soda gefällt und abgesaugt. .. Chlorditrobenzene (1 kg) and m-Amidotetramethyldiamidotriphenylmethane (2 kg) are dissolved in about 10 1 alcohol and heated for a few hours. Then the alcohol distilled off, the residue dissolved in dilute sulfuric acid, the base precipitated with soda and sucked off. .
5 kg Base werden gelöst in 2,6 kg Salzsäure (37 procentig), die Lösung verdünnt mit 400 1 Wasser und unter Kühlung die berechnete Menge Bleisuperoxyd zugefügt. Nach einiger Zeit wird eine Lösung von 5 kg Natriumsulfat in 100 1 Wasser zugesetzt und der Farbstoff nach dem Abfiltriren vom Bleisulfat mit Kochsalz ausgesalzen. Derselbe löst sich in Wasser, besonders beim Ansäuern, mit gelbgrüner Farbe. Das Dinitromonophenyl-m-arnidotetrarnethyldiamidotriphenylcarbinolchlorid fällt aus seinen wässerigen Lösungen als mikrokrystallinischer Niederschlag aus. Beim Trocknen schmilzt er zu einer schwach metallisch glänzenden dunkelgrünen Masse zusammen, welche beim Erkalten hart wird und sich leicht zerreiben läfst.5 kg of base are dissolved in 2.6 kg of hydrochloric acid (37 percent), the solution is diluted with 400 liters Water and, with cooling, the calculated amount of lead peroxide added. After some Time a solution of 5 kg of sodium sulfate in 100 1 of water is added and the dye After filtering off the lead sulphate, salt it out with table salt. It dissolves in water especially when acidified, with a yellow-green color. Dinitromonophenyl-m-arnidotetramnethyldiamidotriphenylcarbinol chloride precipitates from its aqueous solutions as a microcrystalline precipitate. It melts as it dries to a slightly metallic, shiny, dark green mass, which when cooled hardens and is easy to grind.
Der Farbstoff ist schwer löslich in kaltem, leicht löslich in heifsem Wasser, ziemlich leicht in Alkohol und in Essigsäure. In concentrirten Mineralsäuren löst er sich mit braunrother Farbe, welche beim Verdünnen in Grün übergeht. Essigsaures Natron fällt aus den wässerigen Lösungen des Farbstoffes die Farbbase aus. Die Zink- und Bleidoppelsalze des Farbstoffs sind sehr schwer löslich.The dye is sparingly soluble in cold water, easily soluble in hot water, quite easily in alcohol and in acetic acid. In concentrated mineral acids it dissolves with brownish red Color that turns green when diluted. Acetic acid soda falls out of the watery ones Solutions of the dye make up the dye base. The zinc and lead double salts of the dye are very difficult to dissolve.
An Stelle von m-Amidotetramethyldiamidotriphenylmethan läfst sich ebenso die entsprechende Aethylverbindung verwenden.Instead of m-amidotetramethyldiamidotriphenylmethane the corresponding ethyl compound can also be used.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE63026C true DE63026C (en) |
Family
ID=336979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT63026D Expired - Lifetime DE63026C (en) | Process for the preparation of green basic dyes of the triphenylmethane series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE63026C (en) |
-
0
- DE DENDAT63026D patent/DE63026C/en not_active Expired - Lifetime
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