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1,3,5‐Triphenylhexahydro‐1,3,5‐triazine – active intermediate and precursor in the novel synthesis of benzoxazine monomers and oligomers
Author(s) -
Brunovska Zdenka,
Liu Jin Ping,
Ishida Hatsuo
Publication year - 1999
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19990701)200:7<1745::aid-macp1745>3.0.co;2-d
Subject(s) - paraformaldehyde , monomer , bifunctional , chemistry , polymer chemistry , bisphenol a , amine gas treating , triazine , stoichiometry , aryl , proton nmr , bisphenol , 1,3,5 triazine , reaction mechanism , acrylonitrile , organic chemistry , polymer , alkyl , catalysis , copolymer , epoxy
Abstract The benzoxazine monomer synthesis via 1,3,5‐trialkyl(aryl)hexahydro‐1,3,5‐triazine intermediate is followed by 1 H NMR, FT‐IR, and SEC. A model compound, 1,3,5‐triphenylhexahydro‐1,3,5‐triazine, is synthesized independently and its reaction with bisphenol‐A and paraformaldehyde in stoichiometric amounts is also followed by 1 H NMR. Additional model compounds, 1,3,5‐trimethyl(ethyl)hexahydro‐1,3,5‐triazine, are used instead of a primary amine to synthesize bifunctional benzoxazine monomers, bis(3,4‐dihydro‐2 H ‐3‐methyl(ethyl)‐1,3‐benzoxazinyl)isopropane, via novel solventless reaction with bisphenol‐A in the presence of paraformaldehyde. The mechanism of this reaction is proposed.