AMPHIPHILIC POLYMERS FROM LONG-CHAIN (Z)-2-ALKOXYVINYL ACETATES

Five new (Z)-2-alkoxyvinyl acetates (isopropyl, butyl, hexyl, decyl, a nd 10-undecenyl derivatives) have been prepared by a retro-Diels-Alder technique. The synthesis of typical detergent derivatives with long a lkyl residues is markedly improved by using cyclopentadiene instead of anthracene for the Diels-Alder reaction. Amphiphilic polymers were ob tained by cationic homopolymerization of the long-chain derivatives. A s a result of their molecular arrangement, these polymers show a decid edly hydrophobic character. However, a highly water-soluble polymer wi th detergent properties resulted if the amphiphilie geometry of the ho mopolymer of the 10-undecenyl derivative was changed by oxidative clea vage of the terminal side-chain double bond.