Chloromethylation of arylaminoanthraquinones such as four kinds of α-mono-substituents composed of anilino, ο- and m-toluidino and mesidinoanthraquinones, three kinds of bis-compound composed of 1, 4-, 1, 5-, and 1, 8--bis(p-toluidino)-anthraquinones, and 1-hydroxy-4-p-toluidinoanthraquinone were carried out by use of sym-dichlorodimethylether in concentrated sulfuric acid. Each of the chloromethylated compound was isolated and their properties were clarified. The chloromethylated compounds were derived into pyridinium and isothiuronium salts and their availability as the dye has been investigated.
A new preparative method of Biguanide salts using guanyl-ο-alkylisoureas (GOA) was proposed. In this study the preparation of some alkylbiguanide salts were examined and suitable reaction conditions were decided. From this result, it was found that GOA salt reacted smoothly with free amine in apueous solution at room temperature and gave biguanide at good yield. Thus, this is applicable for general synthesis of a biguanide salt from an amine, especially a remarkable availavility was noticed in the case of preparation of lower alkylbiguanide salt. As it is known the preparation : lower alkylbiguanide is slightly conducted by means of ordinary method.
Acylaminoanthraquinones cannot be chloromethylated directly. Accordingly, chloromethylated acylaminoanthraquinones are prepared by the reaction of aminoanthraquinone and chloromethylbenzoyl chloride. Reaction of 1-amino and, 1, 4-, 1, 5-, and 1, 8-diaminoanthraquinones with o-, m-, and p-chloromethylbenzoyl chlorides, respectively, yielded 12 kinds of chloromethyl compounds and the dyeing properties of their pyridinium and isothiuronium salts have been inves tigated.
Chloromethylation of anthraquinonebenzeneacridone and anthraquinonenaph thaleneacridone with sym-dichlorodimethylether in the presence of concentrated sulfuric acid gave mono- and bis-chloromethyl compounds from the former and mono-, his- and trichloromethyl compounds from the latter almost in pure form. The chloromethyl group was first entered into 12-position of anthraquinone benzeneacridone, to give mono chloromethyl compound then it entered into 10-position to give a bis (chloromethyl) compound. These chloromethylated compounds were derived into pyridinium and isothiuronium salts and their dyeing qualit properties were examined.
Chloromethylation of benzanthrone with sym-dichloromethyl ether in the presence of concentrated sulfuric acid gave a bis (chloromethyl) compound and the monochloromethyl compound was not obtained in this case. Decomposition of the his (chloromethyl) compound with chromic acid gave anthraquinone-l, 6-dicar-boxylic acid. This indicated that the chloromethyl groups were entered into Sand 9-positions in the same way as in cationoid reagent. A few derivatives were prepared from the bis-(chloromethyl) comound and the dyeing quapropertieslities of their pyridinium and iso thiuronium salts were examined.