Polyurethanes from novel 1,3-propyleneoxide co-telechelics having pendant hydantoin and methoxymethyl groups

We report the synthesis of a new oxetane monomer 5,5-dimethyl-3-(2-((3-methyloxetan-3-yl)methoxy)ethyl)-imidazolidine-2,4-dione (Hy4Ox, 1), an oxetane with a hydantoin-containing moiety in the 3-position. This hydantoin-oxetane monomer is stable to cationic ring-opening polymerization. Copolymerization of Hy4Ox with another new monomer, 3-methyl-3-methoxymethyloxetane (MOx, 2) provided a series of hydroxy terminated poly(2,2-substituted-1,3-propanediol) co-telechelics (P(Hy4Ox:MOx)) with low Tgs for polyurethane synthesis. 1H NMR spectroscopy was used for establishing stoichiometry and Mn by end group analysis. DSC for P(Hy4Ox:MOx) telechelics shows a single Tg that increases in breadth as the fraction of hydantoin increases suggesting inter- or intrachain hydrogen bonding. The telechelics were incorporated into polyurethanes with HMDI and 1,4-butanediol as the hard block. Characterization of polyurethane composition and bulk properties by 1H NMR, MDSC, and GPC is described. The new monomers and telechelics have promise in optimizing effectiveness of biocidal polyurethane polymeric surface modifiers.