Triallyl monomer bearing adamantane‐like core derived from naturally occurring myo‐inositol: Synthesis and polyaddition with dithiols

Abstract

This paper deals with a triallyl monomer bearing a rigid adamantane‐like core derived from myo‐inositol, a naturally occurring cyclic hexaol. The core structure of the monomer can be readily constructed by orthoesterification of myo‐inositol. The polyaddition of the triallyl monomer with dithiols based on the thermally induced radical thiol‐ene reaction gives the corresponding networked polymers. These networked polymers exhibit much higher thermal stability than the comparative networked polymers obtained from a triallyl monomer bearing less rigid cyclohexyl core. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1193–1199

Partially bio‐based tri‐ and hexaallyl monomers: Synthesis from naturally occurringmyo‐inositol and polyaddition with dithiols

“…2,4,6‐Tri‐ O ‐allyl‐ myo ‐inositol ( 5 ) was synthesized from 2,4,6‐tri‐ O ‐allyl‐ myo ‐inositol 1,3,5‐orthoacetate ( 1 ) by hydrolyzing the orthoester moiety according to a previously reported procedure …”

“…This is because the use of renewable compounds means a reduction in the consumption of fossil‐based resources, and provides more green and sustainable approaches to polymer materials . The focus of our research interest has been on the utilization of myo ‐inositol as a starting material for designing monomers to prepare linear and networked polymers . myo ‐Inositol is a naturally occurring cyclic hexaol that can be obtained from its phosphate derivatives such as phosphatidyl inositol and phytic acid found abundantly in organs of plants and animals .…”

“…The resulting orthoester has three hydroxyl groups. We therefore employed it as a precursor for synthesizing a triallyl monomer 1 , whose radical polyaddition with dithiols afforded the corresponding networked polymers 3 (Scheme ) . In parallel, 1 was converted to another triallyl monomer 2.…”

Radical Polymerization of methacrylates with an adamantane-like rigid core derived from naturally occurringmyo-inositol

“…Its polyaddition with diisocyanates yielded networked polyurethanes with higher T g than networked polyurethanes obtained by polyaddition of 1,3,5‐cyclohexanetriol (CHT) with diisocyanates, indicating the efficacy of incorporating the adamantane‐like rigid core into the crosslinking points for suppressing polymer chain mobility. Further, the same triol 1 was converted into a triallyl ether and its radically induced polyaddition with dithiols was investigated . The resulting networked polymer exhibited higher thermal stability than a polymer obtained from the polyaddition of a triallyl monomer with less rigid cyclohexane core.…”

Rigid triol and diol with adamantane-like core derived from naturally occurringmyo-inositol and their polyaddition with diisocyanates

“…Peng and Kishi have developed conformationally constrained ligands bearing an inositol orthoester core and demonstrated their ability to form bimetallic complexes . Recently, we have reported a triallyl monomer derived from myo ‐inositol orthoester and its use for polyaddition with dithiols . The resulting networked polymers, in which the rigid cyclic orthoester moieties are connected with each other via thioether bonds, exhibited higher T g s than those bearing less rigid cyclohexyl cores.…”