Hyperbranched poly(amine-ester) polyol: Synthesis, characterization, thermal stability, solubility and surface activity

Abstract

AbstractA series of hyperbranched poly(amine-ester) polyols were synthesized by the polycondensation of N,N-diethylol-3-amine-methylpropionate [prepared by the Michael addition reaction of methyl acrylate (MA) with diethanolamine (DEA)] as an AB2-type monomer with trimethylol propane (TMP) as the core moiety, proceeding in one-step procedure in the melt with p-toluenesulfonic acid (p-TSA)as catalyst. The Michael addition reaction and polycondensation behaviors were systematically investigated, in an effort to optimize the reaction conditions, respectively. Optimum parameters for addition reaction: at MA/DEA ratio of 2:1 for 4 h at 35 °C, adding MA to DEA, using methyl alcohol as solvent; and for polymerization: dosage of p-TSA was 2 wt % (based on total weight of AB2-type monomer and core) for 4~5 h at 120 °C, adding monomer to core. The obtained monomer and polymers were characterized by Fourier transform infrared spectroscopy (FTIR), 1H-NMR spectroscopy and gel permeation chromatography (GPC). It was suggested that the hyperbranched poly(amine-ester) polyol formed via a mechanism of a combination of transesterification and addition reactions. The thermal stability, solubility and surface activity in aqueous solution of the polymers were also examined.