DE3047925A1 - Tri:aryl methane dyestuff cpds. with sulphonated benzene ring - useful in printing ink and for toning carbon black - Google Patents

Tri:aryl methane dyestuff cpds. with sulphonated benzene ring - useful in printing ink and for toning carbon black

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Publication number
DE3047925A1
DE3047925A1 DE19803047925 DE3047925A DE3047925A1 DE 3047925 A1 DE3047925 A1 DE 3047925A1 DE 19803047925 DE19803047925 DE 19803047925 DE 3047925 A DE3047925 A DE 3047925A DE 3047925 A1 DE3047925 A1 DE 3047925A1
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methyl
hydrogen
ethyl
radicals
blue
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German (de)
Inventor
Horst Dipl.-Chem. Dr. 6700 Ludwigshafen Bruder
Erwin Dipl.-Chem. Dr. 6900 Heidelberg Hahn
Joachim Dipl.-Chem. Dr. 6830 Schwetzingen Jesse
Udo Dipl.-Chem. Dr. 6710 Frankenthal Mayer
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BASF SE
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BASF SE
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Priority to DE19803047925 priority Critical patent/DE3047925A1/en
Priority to JP56202590A priority patent/JPS57126855A/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

New triarylmethane dyestuffs (I) with a sulphonated benzene ring are of formula (I). In (I) R has formula (II) or (III) R1, R2, R4, R6 and R7 are H, Me or Et, R3 is H, Me, Et or Ph and R5 is Me, Et, Ph, tolyl, methoxyphenyl or ethoxyphenyl. If R1 and R2 are not H, -NR3R4 is -NH2; if -NR3R4 is NEt2, R is not -Q-NMe-Ph (Q is o-phenylene); and if R1 and R2 are H and R is -Q-NH2 or -Q-NH-Ph, no. -NR3R4 is NH2 or -NHPh. (I) are used in printing inks or for toning C black. They are also useful in carbon paper. They are violet to greenish-blue in colour and insoluble in water. (I) can be prepd. by conventional methods, e.g. condensn. of 4,4'-aminobenzophenone with aniline or alpha-naphthylamine and sulphonation, if necessary.

Description

'Triarylmethanfarbstoffe und ihre Verwendung'Triarylmethane dyes and their use

Die Erfindung betrifft Verbindungen, die einensulfierten Benzring enthalten und die in einer der möglichen mesomeren Grenzstrukturen der allgemeinen Formel I entsprechen, in der R einen Rest der Formel und unabhängig voneinander die Reste R1 und R7 Wasserstoff, Methyl oder Ethyl, R2 und R6 Wasserstoff, Methyl oder Ethyl, R3 Wasserstoff, Methyl, Ethyl oder Phenyl, R4 Wasserstoff, Methyl oder Ethyl und R5 Methyl, Ethyl, Phenyl, Tolyl, Methoxyphenyl oder Ethoxyphenyl bedeuten, wobei, wenn R1 und R2 von Wasserstoff verschieden sind, die Reste an den die Reste R1 und R2 tragenden Phenylgruppen eine NER2-Gruppe bedeuten, wobei für -N(C2H5)2 R nicht CH3 R NH2 oder ist und wobei, wenn R1 und R2 H sind und ist, keiner der Reste Amino oder Phenylamino ist.The invention relates to compounds which contain a sulfated benzene ring and which are in one of the possible mesomeric boundary structures of the general formula I. correspond, in which R is a radical of the formula and, independently of one another, the radicals R1 and R7 are hydrogen, methyl or ethyl, R2 and R6 are hydrogen, methyl or ethyl, R3 are hydrogen, methyl, ethyl or phenyl, R4 are hydrogen, methyl or ethyl and R5 are methyl, ethyl, phenyl, tolyl, methoxyphenyl or Ethoxyphenyl, where, when R1 and R2 are different from hydrogen, the radicals on the phenyl groups carrying the radicals R1 and R2 denote a NER2 group, where for -N (C2H5) 2 R not CH3 R NH2 or is and where, when R1 and R2 are H and is, none of the leftovers Is amino or phenylamino.

Zur Herstellung der Verbindungen der Formel I können die üblichen Methoden zur Herstellung von Triarylmethanfarbstoffen verwendet werden, beispielsweise die Kondensation von 4,4'-Aminobenzophenonen mit Anilinen oder « -Naphthylaminen. Besonders vorteilhaft ist die Herstellung nach dem in der US-Patentschrift 3,828,071 beschriebenen Verfahren Die Verbindungen der Formel I erhält man aus den mindestens einen sulfierbaren Benzring enthaltenden Triarylmethanfarbstoffen durch Einführung einer Sulfogruppe nach an sich bekannten Methoden.For the preparation of the compounds of the formula I, the usual Methods for the preparation of triarylmethane dyes are used, for example the condensation of 4,4'-aminobenzophenones with anilines or «-naphthylamines. Production according to that described in US Pat. No. 3,828,071 is particularly advantageous Process described The compounds of formula I are obtained from the at least triarylmethane dyes containing a sulfatable benz ring by introduction a sulfo group according to methods known per se.

Man kann auch von bereits die Sulfogruppe enthaltenden Vorprodukten ausgehen und gelangt dann bei der Herstellung der Triarylmethanfarbstoffe direkt zu Verbindungen der Formel I.It is also possible to use precursors which already contain the sulfo group go out and is then used directly in the manufacture of the triarylmethane dyes to compounds of formula I.

Einzelheiten der Herstellung der erfindungsgemäßen Verbindungen können den Beispielen entnommen werden, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen.Details of the preparation of the compounds according to the invention can can be taken from the examples, which contain information about parts and percentages, unless otherwise noted, based on weight.

'Die erfindungsgemäßen Farbstoffe haben violette bis grünhlaue Farbtöne und sind wasserunlöslich. Sie verhalten sich wie Pigmente und werden nach entsprechendem Finish vorzugsweise in Druckfarben verwendet, u. a. zum Schönen von Ruß enthaltenden Druckfarben.The dyes according to the invention have violet to greenish-blue shades and are insoluble in water. They behave like pigments and are made accordingly Finish preferably used in printing inks, i.a. for the beauty of soot containing Printing inks.

Weiterhin sind sie zur Verwendung in Kohlepapieren geeignet.They are also suitable for use in carbon papers.

Beispiel 1 76,2 g 4,4'-Bis-dimethylaminodiphenylmethan, 50,7 g Diphenylamin, 1,5 g Chloranil und 1,5 g Fe-Komplex des Dihydrodibenzotetraaza[14]annulens*)werden bei 40 - 43 0c in 200 ml Eisessig unter intensiver Rührung mit Sauerstoff begast. Nach 1,5 Stunden ist die Oxidation beendet. Der Ansatz wird in 3 1 Wasser getropft und mit 150 ml HCl konz.Example 1 76.2 g of 4,4'-bis-dimethylaminodiphenylmethane, 50.7 g of diphenylamine, 1.5 g chloranil and 1.5 g Fe complex of dihydrodibenzotetraaza [14] annulens *) gassed with oxygen at 40-43 ° C. in 200 ml of glacial acetic acid with intensive stirring. The oxidation is complete after 1.5 hours. The batch is added dropwise to 3 l of water and with 150 ml HCl conc.

versetzt. Nach Abfiltrieren des ausgefallenen Farbstoffs wird dieser mit 3 1 10 %iger NaCl-Lösung gewaschen und getrocknet. Man erhält 125 g.offset. After the precipitated dye has been filtered off, it becomes washed with 3 l of 10% NaCl solution and dried. 125 g are obtained.

100 g dieses Farbstoffs werden bei 20 °C in 300 g H2SO4 (96 %ig)eingetragen. Man rührt 15 Stunden bei 100 00, gießt den abgekühlten Sulfonierungsansatz in 3 1 Eiswasser, saugt den Feststoff ab und wäscht neutral.100 g of this dye are introduced into 300 g of H2SO4 (96%) at 20 ° C. The mixture is stirred at 100,000 for 15 hours, and the cooled sulfonation batch is poured into 3 1 ice water, sucks off the solid and washes neutral.

Zur Reinigung kann der feuchte Preßkuchen in 3 1 Wasseraufgenommen werden. Man erhitzt auf 90 - 100 °C, setzt 200 ml NaOH(50 %ig) zu (pH 12) und filtriert. Das Filtrat wird mit 130 ml H2SO4 (96 %ig) auf pH 1,9 gebracht. Man trennt das ausgefällte Pigment bei 60 0 ab, wäscht mit Wasser und saugt trocken. Dabei erhält man 361 g eines Preßkuchens mit einem Farbstoffgehalt von 25,8 %, entsprechend 90,6 g ber. trocken.The moist press cake can be taken up in 3 liters of water for cleaning will. The mixture is heated to 90-100 ° C., 200 ml of NaOH (50%) are added (pH 12) and the mixture is filtered. The filtrate is brought to pH 1.9 with 130 ml of H2SO4 (96%). Separate the precipitated Pigment at 60 0, washed with water and sucked dry. This gives 361 g a press cake with a dye content of 25.8%, corresponding to 90.6 g ber. dry.

Dieses Produkt kann feucht oder getrocknet zu für Druckzwecke geeigneten Präparationen nach den üblichen Verfahren weiterverarbeitet werden. Die erhaltenen Drucke sind rotstichig blau.This product can be used damp or dried to be suitable for printing purposes Preparations can be further processed according to the usual procedures. The received Prints are a reddish blue.

* ) siehe DE-OS 23 33 925 und 23 34 918 Durch Variieren der Vorprodukte gelangt man auf ähnliche Weise zu den folgenden Farbstoffen: Bsp. A1 A2 A3 A4 A5 Nuance 2 CH3 CH3 H H CH3 rotstichig blau 3 C2H5 C2H5 H H CH3 rotstichig blau 4 C2H5 H CH3 H CH3 violett 5 H H CH3 CH3 CH3 rotviolett 6 H H C2H5 C2H5 CH3 rotviolett 7 C2H5 C2H5 H H H rotstichig blau 8 C2H5 H CH3 H H rotstichig blau 9 H H CH3 CH3 H rotviolett 10 H H C2H5 C2H5 H rotviolett Beispiel 11 29,8 g p-Dimethylaminobenzaldehyd, 101,5 g Diphenylamin, 200 ml Methanol und 20 ml HCl konz. werden 6 Stunden am Rückfluß erhitzt. Anschließend versetzt man mit 20 ml HCl konz., 1 g Fe-Komplex des Dihydrodibenzotetraaza14-annulens, 1 g Chloranil und oxidiert unter kräftigem Rühren mit Sauerstoff bei 40 - 43 00. Nach 4 Stunden wird der Ansatz zur Fällung in ein Gemisch aus 2 1 Wasser 50 ml HCl konz. und 250 ml Toluol gegossen und abgesaugt.*) see DE-OS 23 33 925 and 23 34 918 By varying the preliminary products, the following dyes are obtained in a similar way: Example A1 A2 A3 A4 A5 Nuance 2 CH3 CH3 HH CH3 reddish blue 3 C2H5 C2H5 HH CH3 reddish blue 4 C2H5 H CH3 H CH3 purple 5 HH CH3 CH3 CH3 red-violet 6 HH C2H5 C2H5 CH3 red-violet 7 C2H5 C2H5 HHH reddish blue 8 C2H5 H CH3 HH reddish blue 9 HH CH3 CH3 H red-violet 10 HH C2H5 C2H5 H red-violet Example 11 29.8 g of p-dimethylaminobenzaldehyde, 101.5 g of diphenylamine, 200 ml of methanol and 20 ml of conc. are refluxed for 6 hours. Then 20 ml of concentrated HCl, 1 g of Fe complex of dihydrodibenzotetraaza14-annulens, 1 g of chloranil are added and the mixture is oxidized with oxygen at 40-4300 while stirring vigorously Water 50 ml HCl conc. and poured 250 ml of toluene and suctioned off.

Nach Aufnehmen des Preßkuchens in 500 ml Toluol wird 2 Stunden bei 70 °C gerührt. Erneutes Absaugen und Trocknen ergibt 103 g eines Farbstoffs, der wie folgt sulfoniert wird: 20 g des Produkts werden bei 15 - 20 °C in 100 g H2SO4(96 %ig)eingetragen. Man rührt 20 Stunden bei Raumtemperatur, gießt den Ansatz in 1 1 Wasser, saugt ab, wäscht mit Wasser und trocknet im Vakuum bei 60 00. Man erhält 19,4 g eines blauen Pigments, das nach entsprechendem Finish zu Druck zwecken verwendet werden kann.After taking up the press cake in 500 ml of toluene, 2 hours at 70 ° C stirred. Renewed suction and drying gives 103 g of a dye which is sulfonated as follows: 20 g of the product are dissolved in 100 g of H2SO4 (96 % ig) entered. The mixture is stirred for 20 hours at room temperature and the batch is poured into 1 1 water, filtered off with suction, washed with water and dried in vacuo at 60,000. This gives 19.4 g of a blue pigment which, after appropriate finish, is used for printing purposes can be.

Durch Variieren der Vorprodukte werden folgende Pigmente erhalten: Bsp. B1 B2 B3 B4 B5 B6 Nuance 12 C2H5 C2H5 H H H H blau 13 H H CH3 CH3 H H violett 14 H H C2H5 C2H5 H H violett 15 C2H5 H CH3 H H H rotstichig blau 16 C2H5 C2H5 H H CH3 H blau 17 CH3 CH3 H H CH3 H blau 18 CH3 CH3 H H H CH3 blau 19 C2H5 C2H5 H H H CH3 blau 20 H H CH3 CH3 H CH3 violett 21 H H C2H5 C2H5 H CH3 violett 22 CH3 H CH3 H H CH3 rotstichig blau 23 C2H5 C2H5 H H CH3 CH3 blau 24 CH3 CH3 H H CH3 CH3 blau Beispiel 25 36 g Viktoriablau B *) werden bei Raumtemperatur innerhalb von ca. 2 Stunden in 180 g H2S04(96 %ig) eingetragen und 1 Stunde nachgerührt. Anschließend erhitzt man auf 60 bis 65 OC. Nach etwa 6 Stunden wird der Ansatz in 700 ml Wasser gegossen, der ausgefallene Farbstoff abgesaugt und neutral gewaschen. Man erhält 78 g eines 40,1 zeigen wasserfeuchten Preßkuchens. Die nach entsprechender Weiterverarbeitung erhältlichen Drucke sind grünstichig blau.By varying the preliminary products, the following pigments are obtained: Example B1 B2 B3 B4 B5 B6 shade 12 C2H5 C2H5 HHHH blue 13 HH CH3 CH3 HH purple 14 HH C2H5 C2H5 HH purple 15 C2H5 H CH3 HHH reddish blue 16 C2H5 C2H5 HH CH3 H blue 17 CH3 CH3 HH CH3 H blue 18 CH3 CH3 HHH CH3 blue 19 C2H5 C2H5 HHH CH3 blue 20 HH CH3 CH3 H CH3 purple 21 HH C2H5 C2H5 H CH3 purple 22 CH3 H CH3 HH CH3 reddish blue 23 C2H5 C2H5 HH CH3 CH3 blue 24 CH3 CH3 HH CH3 CH3 blue Example 25 36 g of Victoria blue B *) are introduced into 180 g of H 2 SO 4 (96%) at room temperature over the course of about 2 hours and the mixture is stirred for a further hour. Then it is heated to 60 to 65 ° C. After about 6 hours, the batch is poured into 700 ml of water, and the dyestuff which has precipitated out is filtered off with suction and washed until neutral. 78 g of a 40.1 show water-moist press cake are obtained. The prints available after further processing are greenish blue.

Durch Variieren der Ausgangsverbindung werden folgende Pigmente erhalten: *) Die Herstellung von Viktoriablau B erfolgt nach literaturbekannten Methoden aus Michlers Keton und Phenyl-cC-naphthylamin, z. B. nach: N.M. Woroshzow: Grundlage der Synthese von Zwischenprodukten und Farbstoffen, Akademie-Verlag, 1966, Berlin, 4. Auflage, S. 883. Bsp. T1 T2 T3 T4 T5 T6 Nuance 26 CH3 CH3 H H H CH3 grünstichig blau 27 CH3 CH3 H H H OCH3 grünstichig blau 28 CH3 CH3 H H H OC2H5 grünstichig blau 29 CH3 CH3 H H CH3 H grünstichig blau 30 C2H5 C2H5 H H CH3 H grünstichig blau 31 C2H5 H CH3 H CH3 H blau 32 H H CH3 CH3 CH3 H blau 33 H H C2H5 C2H5 CH3 H blau 34 C2H5 H CH3 H H H blau 35 H H C2H5 C2H5 H H blau The following pigments are obtained by varying the starting compound: *) Viktoriablau B is prepared by methods known from the literature from Michler's ketone and phenyl-cC-naphthylamine, e.g. B. after: NM Woroshzow: Basis of the synthesis of intermediates and dyes, Akademie-Verlag, 1966, Berlin, 4th edition, p. 883. E.g. T1 T2 T3 T4 T5 T6 Nuance 26 CH3 CH3 HHH CH3 greenish blue 27 CH3 CH3 HHH OCH3 greenish blue 28 CH3 CH3 HHH OC2H5 greenish blue 29 CH3 CH3 HH CH3 H greenish blue 30 C2H5 C2H5 HH CH3 H greenish blue 31 C2H5 H CH3 H CH3 H blue 32 HH CH3 CH3 CH3 H blue 33 HH C2H5 C2H5 CH3 H blue 34 C2H5 H CH3 HHH blue 35 HH C2H5 C2H5 HH blue

Beispiel 36 60,3 g N-Phenyl-1-naphthylamin-8-sulfosäure und 50,8 g 4,4'-Bis-dimethylamino-diphenylmethan werden in 100 ml Eisessig und 100 ml Propylenglykol 4,5 Stunden mit Sauerstoff unter Zusatz von 1 g Fe-Komplex des DihydrodibenzotetraazaEl4]annulens und 1 g Chloranil katalytisch oxidiert. Man gießt den Ansatz in Wasser, filtriert, wäscht den Rückstand mit Wasser und erhält nach Trocknung 113 g eines Pigments, mit dem nach geeignetem Finish grünstichig blaue Drucke erzielt werden.Example 36 60.3 g of N-phenyl-1-naphthylamine-8-sulfonic acid and 50.8 g 4,4'-Bis-dimethylamino-diphenylmethane are dissolved in 100 ml of glacial acetic acid and 100 ml of propylene glycol 4.5 hours with oxygen with the addition of 1 g Fe complex of dihydrodibenzotetraazaEl4] annulens and 1 g of chloranil is catalytically oxidized. The batch is poured into water, filtered, washes the residue with water and, after drying, receives 113 g of a pigment, with which greenish blue prints can be achieved after a suitable finish.

Beispiel 37 Ähnliche Resultate wie in Beispiel 36 werden erhalten, wenn man 60,3 g N-Phenyl-1-naphthylamin-8-sulfosäure durch 62,6 g N-p-tolyl-1-naphthylamin-8-sulfosäure ersetzt.Example 37 Similar results as in Example 36 are obtained if you mix 60.3 g of N-phenyl-1-naphthylamine-8-sulfonic acid with 62.6 g of N-p-tolyl-1-naphthylamine-8-sulfonic acid replaced.

Zeichn. Sign.

L e e r s e i t eL e r s e i t e

Claims (4)

Patentansprüche 1. Triarylmethanfarbstoffe, die einen sulfierten Benzring enthalten und die in einer der möglichen mesomeren Grenzstrukturen der allgemeinen Formel I entsprechen, in der R einen Rest der Formel und unabhängig voneinander die Reste R1 und R7 Wasserstoff, Methyl oder Ethyl, R2 und R6 Wasserstoff, Methyl oder Ethyl, R3 Wasserstoff, Methyl, Ethyl oder Phenyl, R4 Wasserstoff, Methyl oder Ethyl und R5 Methyl, Ethyl, Phenyl, Tolyl, Methoxyphenyl oder Ethoxyphenyl bedeuten, wobei, wenn R1 und R2 von Wasserstoff verschieden sind, die Reste an den die Reste R1 und R2 tragenden Phenylgruppen eine Nfl9-Gruppe bedeuten, wobei für -N(C2H5)2 R nicht ist CH R NH2 oder
und wobei, wenn R1 und R2 H sind und ist, keiner der Reste Amino oder Phenylamino ist.Claims 1. Triarylmethane dyes which contain a sulfated benzene ring and which are in one of the possible mesomeric boundary structures of the general formula I. correspond, in which R is a radical of the formula and, independently of one another, the radicals R1 and R7 are hydrogen, methyl or ethyl, R2 and R6 are hydrogen, methyl or ethyl, R3 are hydrogen, methyl, ethyl or phenyl, R4 are hydrogen, methyl or ethyl and R5 are methyl, ethyl, phenyl, tolyl, methoxyphenyl or Ethoxyphenyl, where, when R1 and R2 are different from hydrogen, the radicals on the phenyl groups carrying the radicals R1 and R2 are an Nfl9 group, where for -N (C2H5) 2 R not is CH R NH2 or
and wherein when R1 and R2 are H and is, none of the leftovers Is amino or phenylamino. 2. Verbindungen gemäß Anspruch 1 der allgemeinen Formel in der die Reste A1 bis A5 unabhängig voneinander Wasserstoff, Methyl oder Ethyl sind, wobei für NH2 einer der Reste A3 bis A5 von Wasserstoff verschieden ist und wobei für -N(C2H5)2 A5 nicht Methyl ist. 2. Compounds according to claim 1 of the general formula in which the radicals A1 to A5 are independently hydrogen, methyl or ethyl, where for NH2 is one of the radicals A3 to A5 different from hydrogen and where -N (C2H5) 2 A5 is not methyl. 5. Verbindungen gemäß Anspruch 1 der allgemeinen Formel in der die Reste B1 bis B6 unabhängig voneinander Wasserstoff, Methyl oder Ethyl sind, wobei die Reste B1 bis B6 nicht gleichzeitig Wasserstoff sind.5. Compounds according to claim 1 of the general formula in which the radicals B1 to B6 are independently hydrogen, methyl or ethyl, the radicals B1 to B6 not being hydrogen at the same time. 4. Verbindungen gemäß Anspruch 1 der allgemeinen Formel in der die Reste T1 bis T4 unabhängig voneinander Wasserstoff, Methyl oder Ethyl sind und R4 und R5 die für Anspruch 1 angegebenen Bedeutungen haben.4. Compounds according to claim 1 of the general formula in which the radicals T1 to T4 are independently hydrogen, methyl or ethyl and R4 and R5 have the meanings given for claim 1. 5, Verwendung der Verbindungen gemäß Anspruch 1 in Druckfarben oder zum Schönen von Ruß.5, use of the compounds according to claim 1 in printing inks or to beautify soot.
DE19803047925 1980-12-19 1980-12-19 Tri:aryl methane dyestuff cpds. with sulphonated benzene ring - useful in printing ink and for toning carbon black Withdrawn DE3047925A1 (en)

Priority Applications (2)

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DE19803047925 DE3047925A1 (en) 1980-12-19 1980-12-19 Tri:aryl methane dyestuff cpds. with sulphonated benzene ring - useful in printing ink and for toning carbon black
JP56202590A JPS57126855A (en) 1980-12-19 1981-12-17 Triaryl methane dye and use

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0502200A1 (en) * 1990-08-30 1992-09-09 Fujicopian Co., Ltd. Printer ink composition and printing medium prepared therefrom

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140142262A (en) * 2012-03-29 2014-12-11 미쓰비시 가가꾸 가부시키가이샤 Triarylmethane compound, colored resin composiiton, color filter, liquid crystal display device, and organic el display device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0502200A1 (en) * 1990-08-30 1992-09-09 Fujicopian Co., Ltd. Printer ink composition and printing medium prepared therefrom
EP0502200A4 (en) * 1990-08-30 1993-07-07 Fujicopian Co., Ltd. Printer ink composition and printing medium prepared therefrom
US5279655A (en) * 1990-08-30 1994-01-18 Fujicopian Co., Ltd. Printer ink composition and printing medium using the same

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