SYNTHESIS AND CHARACTERIZATION OF POLYMERS CONTAINING NAPHTHYL-2H-BENZOTRIAZOLES .1. MONOMER SYNTHESIS AND CHARACTERIZATION

2-(2-Hydroxynaphthyl)-2H-benzotriazoles were synthesized by azo coupling of o-nitrobenzene diazonium chloride with 2,3-, 2,5-, and 2,7-dihydroxynaphthalenes, respectively, followed by reductive cyclization with zinc powder and sodium hydroxide. The mode of coupling reactions has been elucidated using NMR spectroscopy and showed that the coupling occurred at the alpha-position of the dihydroxynaphthalenes. The treatment of 2-(2,7-dihydroxynaphthyl)-2H-benzotriazole with acryloyl or methacryloyl chloride, respectively, gave the corresponding (meth)acryloyloxynaphthyl-2H-benzotriazoles, which, along with their methoxy and chloro derivatives, provide a new class of polymerizable UV absorbers.