キナクリドン系有機顔料に関する研究(第3報) : 線型キナクリドン誘導体の合成および顔料的性質

概要

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Although linear type quinacridone (1) has red or rd purple coloration and is used as an organic pigment, the values of linear type quinacridone derivatives having various substituent groups as the pigment are not known. Twenty two kinds pf derivatives having substituent groups, chloro-, methyl- and methoxygroups, were synthesized by the author, their colors and the properties of crystal transition by immersion in dimethylformamide have been investigated with an object of finding valuable pigment. The results obtained are as follows: (1) Twenty kinds of diethyl 3, 6-dihydro-2, 5-diarylaminoterephthalate were newly prepared and their m.p. were given. (2) In the 4, 8- and 2, 6-substituents, blue coloration was increased in the order of chloro, methyl and methoxy group; also, the blue coloration was stronger in 2, 6- than 4, 8-substituent when the substituent groups were the same. (3) In case of immersion in boiling dimethylformamide, methyl substituent showed crystal transition easily but some of chloro and methoxy substituents were difficult to show crystal transition, especially those having chloro or methoxy group in 2-, 3-, 6-, and 7-position. (4) 3, 4, 7, 8-Tetrachloro derivative (orange color), 1, 2, 5, 6-tetrachloro derivative (red color), and 2, 6-dimethoxy derivative (purple color) were found to be valuable as the pigment from their coloration and difficulty of crystal ansition. Also, their syntheses by Friedel-Crafts reaction were established.