1,3,5-Triphenylhexahydro-1,3,5-triazine – active intermediate and precursor in the novel synthesis of benzoxazine monomers and oligomers

✍ Scribed by Zdenka Brunovska; Jin Ping Liu; Hatsuo Ishida

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 107 KB
• Volume: 200
• Category: Article
• ISSN: 1022-1352
• DOI: 10.1002/(sici)1521-3935(19990701)200:7<1745::aid-macp1745>3.0.co;2-d

✦ Synopsis

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-1,3,5triazine, are used instead of a primary amine to synthesize bifunctional benzoxazine monomers, bis(3,4-dihydro-2H-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.