Synthesis of N-[(1,1-dimethyl-2-acetyl)ethyl]-β-dihydroxyethylamine and study of the kinetics of the Michael addition reaction of diacetone acrylamide with diethanolamine

Abstract

A new crosslinker, N-[(1,1-dimethyl-2-acetyl)ethyl]-β-dihydroxyethylamine (DDP), which contains two hydroxyl groups and carbonyl, was successfully synthesized by Michael addition reaction between diacetone acrylamide (DAAM) and diethanolamine (DEA) in different solvents. This crosslinker could crosslink during film formation through a reaction between ketone and hydrazide. The structure of DDP was characterized by IR and NMR, and effects of solvents, temperature, and reaction time on the yield of DDP were determined. The reaction kinetics including the order of the reaction and apparent activation energy were also investigated. Under the experimental conditions chosen (temperature 90 °C, reaction time 12 h), the crosslinker was obtained in 75.28% yield. The reaction was a second-order reaction and the apparent activation energy was 91.0 kJ mol⁻¹. The reaction rate constants were 0.11 mol⁻¹ dm³ h⁻¹ at 90 °C and 0.03 mol⁻¹ dm³ h⁻¹ at 75 °C.