Oxidative coupling copolymerization between 2,6-dimethylphenol (DMP) and functional monomers containing hydroxyl and amino groups, 2-hydroxymethyl-6-methylphenol and 2-(4-methylphenylamino)methyl-6-methylphenol, was carried out with a Cu catalyst under an O-2 atmosphere. The polymerization was significantly affected by the polymerization solvent used, and the copolymers were effectively obtained by polymerization in polar solvents, such as a mixed solvent system containing methanol. The obtained copolymer containing hydroxyl groups was further transformed into polymers containing ester and urethane groups, which were used as additives for the fabrication of polyurethane films. The tensile properties of the films containing the obtained copolymers were significantly improved compared to those of films prepared without an additive, as well as films containing the homo-polymer of DMP. (C) 2014 Elsevier B.V. All rights reserved.