Novel Chiral and Achiral Benzoxazine Monomers and Their Thermal Polymerization

New chiral and achiral benzoxazine monomers (S)-α-3-methylbenzyl-3,4-dihydro-6,8-di-tert-butyl-2H-1,3-benzoxazine and rac-α-3-methylbenzyl-3,4-dihydro-6,8-di-tert-butyl-2H-1,3-benzoxazine were prepared by Mannich condensation from enantiomerically pure (S-α) and racemic (rac) methylbenzylamine H2NCH...

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Bibliographic Details
Published in:Macromolecules 2009-06, Vol.42 (12), p.4008-4015
Main Authors: Ejfler, J, Krauzy-Dziedzic, K, Szafert, S, Lis, T, Sobota, P
Format: Article
Language:English
Subjects:
Applied sciences
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polymerization
Preparation, kinetics, thermodynamics, mechanism and catalysts
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Summary:New chiral and achiral benzoxazine monomers (S)-α-3-methylbenzyl-3,4-dihydro-6,8-di-tert-butyl-2H-1,3-benzoxazine and rac-α-3-methylbenzyl-3,4-dihydro-6,8-di-tert-butyl-2H-1,3-benzoxazine were prepared by Mannich condensation from enantiomerically pure (S-α) and racemic (rac) methylbenzylamine H2NCH(CH3)C6H5, formaldehyde and 2,4-di-tert-butylphenol. Their DSC exhibit exotherms at 291 and 263 °C which correspond to oxazine thermal polymerization. The resulted polymers show very low T g values of 31 and 19 °C for poly-S-1 and poly-rac-1, respectively. Higher value for the polymer obtained from enantiomerically pure monomer results from the monomer derived stereoregularity of the polymer. A comparison of thermal stabilities of both polymers showed significantly lower heat resistance for the polymer obtained from racemic monomer. The resulted data are compared with those obtained for similar rac-α-3-methylbenzyl-3,4-dihydro-8-(1,1,3,3-tetra-methylbutyl)-2H-1,3-benzoxazine with a free ortho position at the phenyl.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma900336m