Functional 1,3-benzoxazine bearing 4-pyridyl group: Synthesis and thermally induced polymerization behavior

ABSTRACT 1,3‐benzoxazine 1, bearing 4‐pyridyl moiety on the nitrogen atom, was synthesized from p‐cresol, 4‐aminopyridine, and paraformaldehyde. The efficient synthesis was achieved by adding acetic acid to suppress the strong basicity caused by the presence of 4‐aminopyridine derivatives. Upon heat...

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Published in:Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2014-02, Vol.52 (3), p.410-416
Main Authors: Kawaguchi, Asei William, Sudo, Atsushi, Endo, Takeshi
Format: Article
Language:English
Subjects:
Acetic acid
Applied sciences
benzoxazine
Exact sciences and technology
heteroatom-containing polymer
metal-polymer complexes
Organic polymers
Physicochemistry of polymers
Polymerization
Preparation, kinetics, thermodynamics, mechanism and catalysts
ring-opening polymerization
structure
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Summary:ABSTRACT 1,3‐benzoxazine 1, bearing 4‐pyridyl moiety on the nitrogen atom, was synthesized from p‐cresol, 4‐aminopyridine, and paraformaldehyde. The efficient synthesis was achieved by adding acetic acid to suppress the strong basicity caused by the presence of 4‐aminopyridine derivatives. Upon heating 1 at 180 °C, it underwent the thermally induced ring‐opening polymerization. The resulting polymer was composed of two types of repeating unit, i.e., (1) Mannich‐type one (‐phenol‐CH2‐NR‐CH2‐) that can be expected from the general ring‐opening polymerization of conventional benzoxazines and (2) a typical phenolic resin‐type one (‐phenol‐CH2‐phenol‐) induced by release of 4‐aminopyridine and paraformaldehyde (unit B). Another structural feature of the polymer was that it possessed a benzoxazine moiety at the chain end. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 410–416 A novel 1,3‐benzoxazine 1 with 4‐aminopyridyl moiety is synthesized from 4‐aminopyridine, p‐cresol, and paraformaldehyde. 1 undergoes the thermally induced ring‐opening polymerization at 180 °C to afford the corresponding polymer composed of two types of repeating units, that is, Mannich‐type one (–phenol–CH2–NR–CH2–) and a typical phenolic resin‐type one (–phenol–CH2–phenol–). The polymer possesses a benzoxazine moiety at the chain end.
ISSN:0887-624X
1099-0518
DOI:10.1002/pola.27015