Cationic and zwitterionic polymerizable surfactants: Quaternary ammonium dialkyl maleates. 1. Synthesis and characterization

Cationic and zwitterionic reactive dialkyl maleates with different hydrophobic chain lengths (R = C10H21, C12H25, C16H33, and C18H37), and some similar surfactants without double bonds were synthesized with an aim to use them as stabilizers in the batch and seeded emulsion copolymerization of styrene and butyl acrylate (part 2 of this series). Surfactants are obtained in a three-step synthesis, starting from ring opening of maleic anhydride, followed by O alkylation with an aminoalkyl compound, and finishing with quaternization of the amino group in the hydrophilic part of the molecule. The chemical structure of surfactants was confirmed by H-1 NMR. Melting points and critical micelle concentrations of the synthesized surfactants were measured. The specific area per molecule at the air/water interface was calculated for most of the surfactants. The adsorption of the surfactant on the polystyrene (PS) and PS/poly(butyl acrylate) copolymer was also measured, and the specific area occupied by the surfactant molecule was calculated in one example.