Cyclodextrins in polymer synthesis: free radical polymerization of cyclodextrin complexes with oxazoline-functionalized vinyl monomers as guest molecules in aqueous medium

Communication: The synthesis of five new oxazoline functionalized vinyl mon omers N-[4-(4',5'-dihydrooxazol-2-yl)phenyl]acrylamide (3a). N-[4-(4',5'-di hydrooxazol-2- yl)phenyl]-2-methylacrylamide (3b), N-(10-[-4-(4',5'-dihydro oxazol-2-yl)phenylcarbamoyl]decyl}-2-acrylamide (5a). N-{10-[4-(4',5'-dihyd rooxazol-2-yl)phenylcarbamo yl]decyl)-2-methylacrylamide (5b) and N-[4-(4', 5'-dihydrooxazol-2-yl)-phenyl]-4-vinylbenzamide (7) is described. With an e quimolar amount of 2,6-dimethyl-beta-cyclo-dextrin (DMCD) these monomers fo rmed hydrophilic inclusion complexes 3a,b-DMCD, 5a,b-DMD and 7-DMCD. These complexes were polymerized radically in an aqueous medium. Resulting polyme rs P-(3a,b). P-(5a,b) and P-(7) precipitated Juring the polymerization due to unthreading of the cyclodextrin from the growing polymer chain. The rema ining oxazoline moiety offers possibilities of further modification of the polymers, e.g. grafting in a cationic ring opening polymerization with comm ercially available alkyloxazolines.