Hemiesters and hemiamides of maleic and succinic acid: synthesis and application of surfactants in emulsion polymerization with styrene and butyl acrylate

Hemiesters and hemiamides of maleic acid with different chain lengths of the hydrophobic alkyl group (R = C8H17, C10H21, C12H25, C16H33) have been synthesized and used as surfactants in the emulsion polymerization of styrene and butyl acrylate. The same polymerization experiments were also carried out using nonreactive surfactants with an analogous succinic structure. The chemical structure of the surfactants was confirmed by 1H nuclear magnetic resonance. The melting point and critical micelle concentration of the reactive surfactants described herein were measured. All of the surfactants studied provided good stability of styrene/butyl acrylate latexes, when compared with a reference late…

Methacrylic maleic bifunctional stabilizer in emulsion polymerization

Films from styrene–butyl acrylate lattices using maleic or succinic surfactants: mechanical properties, water rebound and grafting of the surfactants

Abstract A series of anionic and zwitterionic maleic surfactants have been synthesized and engaged in styrene–butyl acrylate emulsion polymerization. Some non-reactive succinic analogs have been synthesized in order to perform their comparison with the maleic surfactants in polymerization experiments. Films from the obtained lattices were cast, and their mechanical properties and the water rebound were tested. The results of water rebound demonstrate significant difference between the films prepared with maleic or succinic surfactants. Water rebound of the films after 34 days in the case of succinic surfactants was found to be between 51 and 95%, while for maleic surfactants it is only 25–4…

Controlled radical polymerization of styrene in miniemulsion polymerization using reversible addition fragmentation chain transfer

Abstract Miniemulsion polymerizations of styrene in the presence of two reversible addition–fragmentation chain-transfer (RAFT) agents were studied. The rates were significantly retarded by the presence of a RAFT agents S -(thiobenzoyl)thioglycolic acid, 1 , or dithiobenzoic acid 1-phenylethyl ester, 2 . Control in miniemulsion polymerization is not as good as for bulk polymerizations. The miniemulsions could also be stabilized against Ostwald ripening by a polymer terminated by a dithiobenzoic moiety. In this case, the polymerization was not controlled because of the generation of renucleated particles. To cite this article: I. Uzulina et al., C. R. Chimie 6 (2003).

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…

Synthesis and NMR characterization of new poly(ethoxyalkyl) maleates

Polymerizable surfactants derived from maleic anhydride have been synthesized. The hydrophilic part is obtained by a controlled ethylene oxide polymerization according to a new heterogeneous catalytic process. Some maleates derivatives have been obtained and fully characterized by 1H and 13C NMR. Their cmc were also measured. Some of them have been engaged in styrene emulsion polymerization in which monodisperse latex particles have been produced.

Nonionic Maleic Surfmers

ABSTRACT A set of nonionic maleic surfactants have been prepared, all coming from the derivatization of maleic hemiesters with a long alkyl chain. They are either amidoesters or diester products. In the case of amidoesters, the acid group was first activated and then reacted with primary or secondary or tertiary ethanolamine compounds. In the case of diesters, the hemiester was reacted directly with glycidol, in acid or basic conditions. These surfactants were characterized for their structure by 1H NMR, and for their surface active properties, by surface tension measurements. They were also used in batch emulsion polymerisation of styrene, and seeded core-shell copolymerisation of a 1/1 mi…

Synthesis of Polymer Colloids Using Polymerizable Surfactants

A series of new anionic surfactants were prepared by reacting a polymerizable alcohol with either maleic or succinic anhydride, as well as sulfosuccinic anhydride, resulting in either bireactive or monoreactive surfactants, either carboxylated or sulfonated. The synthesis presented and the critical micelle concentration (CMC) determined. These compounds were engaged in the emulsion polymerization of styrene in batch and also in semi-batch seeded copolymerization producing core-shell latexes. The core was a polystyrene seed prepared using sodium dodecyl sulfate (SDS), thoroughly purified through ion exchange resins. The seed was then swollen overnight with a small amount of a 1 : 1 mixture o…

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…