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Synthesis and characterization of poly{hexakis[(methyl)(4-hydroxyphenoxy)]cyclotriphosphazene}



The reaction of methylhydroquinone with hexachlorocyclotriphosphazene in the presence of a base, 4-picoline, in cyclohexane was investigated. Nuclear magnetic resonance spectroscopy, multiangle laser light scattering, and elemental analyses were performed on the product and two other related phosphazene materials produced by analogous synthetic routes: poly[hexakis(4-hydroxyphenoxy)cyclotriphosphazene] (1) and hexakis[(3-tert-butyl)(4-hydroxyphenoxy)]cyclotriphosphazene (2). Unlike the data for 2 where the tert-butyl moiety enforced regiospecific nucleophilic addition, the data for the methylhydroquinone-substituted cyclotriphosphazene product indicate that the less sterically bulky methyl group provides only limited protection for the adjacent hydroxyl group. The result is the formation of a low molecular weight oligomer, poly{hexakis[(methyl)(4-hydroxyphenoxy)]cyclotriphosphazene} (3), instead of a discrete cyclic trimer species. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 3439–3446, 2001