4-Isopropenyl phenol (4-IPP) is a versatile dual functional intermediate that can be prepared readily from bisphenol-A (BPA). Through etherification with epichlorohydrin to the phenolic group of 4-IPP, it can be converted into 4-isopropenyl phenyl glycidyl ether (IPGE). On further reaction with carbon dioxide in the presence of tetra-n-butyl ammonium bromide (TBAB) as the catalyst, IPGE was transformed into 4-isopropenylphenoxy propylene carbonate (IPPC) in 90% yield. Cationic polymerization of IPPC with strong acid such as trifluoromethanesulfonic acid or boron trifluoride diethyl etherate as the catalyst at -40 degrees C gave a linear poly(isopropenylphenoxy propylene carbonate), poly(IPPC), with multicyclic carbonate groups substituted uniformly at the side-chains of the polymer. The cyclic carbonate groups of poly(IPPC) were further reacted with different aliphatic amines and diamines resulting in formation of polymers with hydroxy-polyurethane on side-chains. Syntheses, characterizations of poly(IPPC) and its conversion into hydroxy-polyurethane crosslinked polymers were presented. (c) 2015 Wiley Periodicals, Inc.