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

✍ Scribed by Thomas A. Luther; Frederick F. Stewart; Robert P. Lash; John E. Wey; Mason K. Harrup

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 174 KB
• Volume: 82
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/app.2205

✦ Synopsis

Abstract

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