Amphiphilic Polymers from Long-Chain (Z)-2-Alkoxyvinyl Acetates

Abstract

Five new (Z)-2-alkoxyvinyl acetates (isopropyl, butyl, hexyl, decyl, and 10-undecenyl derivatives) have been prepared by a retro-Diels−Alder technique. The synthesis of typical detergent derivatives with long alkyl residues is markedly improved by using cyclopentadiene instead of anthracene for the Diels−Alder reaction. Amphiphilic polymers were obtained by cationic homopolymerization of the long-chain derivatives. As a result of their molecular arrangement, these polymers show a decidedly hydrophobic character. However, a highly water-soluble polymer with detergent properties resulted if the amphiphilic geometry of the homopolymer of the 10-undecenyl derivative was changed by oxidative cleavage of the terminal side-chain double bond.

Association in Solution and Adsorption at an Air−Water Interface of Alternating Copolymers of Maleic Anhydride and Styrene

“…Part of the reason may be the complex behavior and the strong tendency of such polyelectrolytes to undergo various conformational transitions 6,7 induced by changes in pH or ionic strength. The ability of these copolymers to assemble and form either intramolecular [8][9][10] or intermolecular [11][12][13][14] associates has already been reported. However, many fundamental aspects remain unclear such as the driving force for the association and the morphology of lowest energy.…”