Synthesis and cationic polymerization of 5-(2,3-epoxypropyl)amino-2-phenyl-1,2,3-benzotriazole

Synthesis and cationic polymerization of the new monomer 5-(2,3-epoxypropyl)amino-2-phenyl-1,2,3-benzotriazole (EAPB) is reported. The monomer was prepared either in the reaction of 5-amino-2-phenyl-1,2,3-benzotriazole with 1-chloro-2,3-epoxypropane or by the treatment of 5-(3-chloro-2-hydroxypropyl)amino-2-phenyl-1,2,3-benzotriazole with sodium hydroxide, Polymerization of EAPB with boron trifluoride diethyl etherate yielded the oligomers with the average degree of polymerization of 4-5. The limit conversion of the monomer did not exceed 53%. The introduction of 1,2-ethane diol into the reaction mixture led to the higher yield of the oligomer. Investigation of polymerization of EAPB by GPC and microcalorimetry as well as analysis of the resulting oligomers by IR spectrometry has shown that, in the presence of 1,2-ethanediol, the reaction proceeds by an activated monomer mechanism, whereas in the absence of the diol, it proceeds by the conventional active chain end mechanism. (C) 2000 Elsevier Science Ltd. All rights reserved.