Maleic diamide polymerizable surfactants. Applications in emulsion polymerization
Abstract A series of new polymerizable non-ionic and ionic surfactants (surfmers) with amides groups on both sides of the C=C double bonds have been prepared upon reaction of maleic isoimide carrying a long alkyl chain (or a benzyl group) with a hydrophilic amine derivative. Their critical micellar concentration (CMC) was measured with a surface tensiometer. They have been engaged in batch emulsion polymerization of styrene, and semi-batch seeded copolymerization of styrene and butyl acrylate, giving stable latexes during the polymerization process, and upon extraction with ethanol, showing a high rate of incorporation at the particle surface. However these surfmers do not confer good steri…
Reactions of Maleisomides with Alcohols
Abstract New surfactants (surfmers) with various amide and ester groups next to C˭C double bonds have been obtained. Maleic acid amidesters (AE) with different hydrophobic groups at the nitrogen atom and hydrophilic substituents at oxygen atoms were synthesized starting with maleic isoimides. 1H KMR and IR spectra were used for their characterization. Some were further characterized for their critical micellar concentration (CMC). A few cationic and zwitterionic surfmers were also prepared from isoimide precursors and characterized. All these surfmers were applied in batch emulsion polymerization of styrene, and in core‐shell seeded copolymerization of styrene and butylacrylate to give late…
Propanephosphonic Acid Anhydride–Mediated Cyclodehydration of Maleic Acid Monoamides
Abstract Propanephosphonic acid anhydride (T3P) has been proposed as a novel reagent for the preparation of maleic acid isoimides from the corresponding monoamides. A series of substituted aromatic and aliphatic isoimides have been prepared in good yields. The main advantage of this synthetic method is the use of environmentally benign, cost-efficient reagents and solvents, which are also safer to handle than the ones employed previously. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.