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Preparation and properties of some thermosets derived from allyl‐functional naphthoxazines
Author(s) -
Agag Tarek
Publication year - 2006
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.23502
Subject(s) - aniline , allylamine , thermogravimetric analysis , monomer , polymer chemistry , polymerization , thermosetting polymer , thermal stability , materials science , chemistry , organic chemistry , polymer , polyelectrolyte , composite material
A series of novel naphthoxazine monomers containing allyl functionalities were synthesized from the reaction of 1‐naphthol, 2‐naphthol, and 1,5‐dihdroxynaphthalene with allylamine and formalin. Another series of naphthoxazines were similarly prepared by using aniline instead of allylamine for comparison. The chemical structures of these novel monomers were confirmed by IR, 1 H NMR, and elemental analysis. DSC of the aniline‐ based naphthoxazines showed an exotherm due to the ring‐opening polymerization of oxazine. For allylamine‐based naphthoxazines, two exotherms were observed. The first exotherm is attributed to the thermal crosslinking of the allyl group and the second is due to the ring‐ opening polymerization of oxazine. The thermal cure of the allylamine‐based naphthoxazine monomers gave thermoset resins with novel structure comprising of polynaphthoxazine with extended network via the polymerization of allyl functionalities. Dynamic mechanical analyses and thermogravimetric analyses showed that the thermosets derived from allyl‐ functional naphthoxazines have high T g 's and stable storage moduli to higher temperature as well as better thermal stability than that of aniline‐based naphthoxazines. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 3769–3777, 2006