Hydrogen-bonded supramolecular polymer networks

R.F.M. Lange, M. Gurp, van, E.W. Meijer

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Abstract

The strong dimerizing, quadruple hydrogen-bonding ureido-pyrimidone unit was used to obtain reversible polymer networks via a synthetic route from com. available starting materials. The hydrogen-bonding ureido-pyrimidone network was prepd. using 3- and 4-isocyanatomethyl-1-methylcyclohexyl-isocyanate (IMCI) in the regioselective coupling reaction of multi-hydroxy functionalized ethylene oxide-propylene oxide copolymers with isocytosines. 1H- and 13C-NMR, IR, MS, and ES-MS anal., performed on a model reaction using butanol, demonstrated the formation of the hydrogen-bonding ureido-pyrimidone unit in a yield of more than 95%. The well-defined, strong hydrogen-bonding ureido-pyrimidone network was compared with a traditional covalently bonded polymer network, a multi-directional hydrogen-bonded polymer network based on urea units, and a ref. compd. The advantage of the reversible, hydrogen-bonded polymer networks is the formation of the thermodynamically most favorable products, which show a higher virtual mol. wt. and shear modulus, compared to the irreversible, covalently bonded polymer network. The properties of the ureido-pyrimidone network are unique; the well-defined and strong dimerization of the ureido-pyrimidone unit does not require any addnl. stabilization such as crystn. or other kinds of phase sepn., and displays a well-defined viscoelastic transition. The ureido-pyrimidone network represents the first example of a truly reversible polymer network showing these features. Furthermore, the ureido-pyrimidone dimerization is strong enough to construct supramol. materials possessing acceptable mech. properties
Original languageEnglish
Pages (from-to)3657-3670
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume37
Issue number19
DOIs
Publication statusPublished - 1999

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