Synthesis and characterization of poly{hexakis[(methy1)(4-hydroxyphenoxy)]cyclotriphosphazene}

Citation
Ta. Luther et al., Synthesis and characterization of poly{hexakis[(methy1)(4-hydroxyphenoxy)]cyclotriphosphazene}, J APPL POLY, 82(14), 2001, pp. 3439-3446
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science","Material Science & Engineering
Journal title
JOURNAL OF APPLIED POLYMER SCIENCE
ISSN journal
00218995 → ACNP
Volume
82
Issue
14
Year of publication
2001
Pages
3439 - 3446
Database
ISI
SICI code
0021-8995(200112)82:14<3439:SACOP>2.0.ZU;2-N
Abstract
The reaction of methylhydroquinone with hexachlorocyclotriphosphazene in th e presence of a base, 4-picoline, in cyclohexane was investigated. Nuclear magnetic resonance spectroscopy, multiangle laser light scattering, and ele mental analyses were performed on the product and two other related phospha zene materials produced by analogous synthetic routes: poly[hexakis(4-hydro xyphenoxy)cyclotriphosphazene] (1) and hexakis[(3-tert-butyl)(4-hydroxyphen oxy)]cyclotriphosphazene (2). Unlike the data for 2 where the tert-butyl mo iety enforced regiospecific nucleophilic addition, the data for the methylh ydroquinone-substituted cyclotriphosphazene product indicate that the less sterically bulky methyl group provides only limited protection for the adja cent 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. (C) 2001 John Wiley & Sons, I nc.