Rigid triol and diol with adamantane‐like core derived from naturally occurring myo‐inositol and their polyaddition with diisocyanates

Two orthoester derivatives 1 and 2 that are easily accessible from naturally occurring myo‐inositol were exploited as new triol‐ and diol‐type monomers bearing a rigid adamantane‐like structure to polyaddition with diisocyanates that gave the corresponding networked and linear polyurethanes. DSC analysis of the networked polyurethanes revealed their high glass transition temperatures ranging from 155 to 248 °C, suggesting the contribution of the rigidity of the adamantane‐like structure introduced at the nodes of the networked polyurethanes 6. Besides, the polyaddition of 2 with diisocyanates gave the corresponding linear polyurethanes 4, of which glass transition temperatures were high, ranging from 105 to 177 °C, presumably by virtue of the rigidity of the adamantane‐like structure introduced into the main chains. T_gs of the networked polyurethanes 6 were higher than those of the linear polyurethanes 4. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 3498–3505