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Primary Amine-Functional Benzoxazine Monomers and Their Use for Amide-Containing Monomeric Benzoxazines

Agag, Tarek; Rodriguez Arza, Carlos LU ; Maurer, Frans LU and Ishida, Hatsuo (2010) In Macromolecules 43(6). p.2748-2758
Abstract
Amino-functional benzoxazine monomers have been successfully prepared. Several routes have been applied to incorporate amino group into benzoxazine structure. These approaches include reduction of the corresponding nitro-functional benzoxazines and deprotection of protected amino-functional benzoxazine monomers. Various approaches that allow primary amine groups to be prepared without damaging the existing benzoxazine groups have been evaluated. Tetrachlorophthalimide and trifluoroacetyl are found to be suitable protecting groups. In addition, a model compound of amide-functional benzoxazines is prepared from primary amine-functional benzoxazine. Fourier transform infrared spectroscopy (FTIR) and H-1 and C-13 nuclear magnetic resonance... (More)
Amino-functional benzoxazine monomers have been successfully prepared. Several routes have been applied to incorporate amino group into benzoxazine structure. These approaches include reduction of the corresponding nitro-functional benzoxazines and deprotection of protected amino-functional benzoxazine monomers. Various approaches that allow primary amine groups to be prepared without damaging the existing benzoxazine groups have been evaluated. Tetrachlorophthalimide and trifluoroacetyl are found to be suitable protecting groups. In addition, a model compound of amide-functional benzoxazines is prepared from primary amine-functional benzoxazine. Fourier transform infrared spectroscopy (FTIR) and H-1 and C-13 nuclear magnetic resonance spectroscopy (NMR) are used to characterize the structure of the monomers. The polymerization behavior of amino-functional monomers and model compound are studied by differential scanning calorimetry (DSC). (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Macromolecules
volume
43
issue
6
pages
2748 - 2758
publisher
The American Chemical Society
external identifiers
  • wos:000275711300016
  • scopus:77951886917
ISSN
0024-9297
DOI
10.1021/ma902556k
language
English
LU publication?
yes
id
09076a9c-052d-4d00-bdae-b633f6e65a41 (old id 1587953)
date added to LUP
2010-04-22 12:56:44
date last changed
2018-06-03 03:16:28
@article{09076a9c-052d-4d00-bdae-b633f6e65a41,
  abstract     = {Amino-functional benzoxazine monomers have been successfully prepared. Several routes have been applied to incorporate amino group into benzoxazine structure. These approaches include reduction of the corresponding nitro-functional benzoxazines and deprotection of protected amino-functional benzoxazine monomers. Various approaches that allow primary amine groups to be prepared without damaging the existing benzoxazine groups have been evaluated. Tetrachlorophthalimide and trifluoroacetyl are found to be suitable protecting groups. In addition, a model compound of amide-functional benzoxazines is prepared from primary amine-functional benzoxazine. Fourier transform infrared spectroscopy (FTIR) and H-1 and C-13 nuclear magnetic resonance spectroscopy (NMR) are used to characterize the structure of the monomers. The polymerization behavior of amino-functional monomers and model compound are studied by differential scanning calorimetry (DSC).},
  author       = {Agag, Tarek and Rodriguez Arza, Carlos and Maurer, Frans and Ishida, Hatsuo},
  issn         = {0024-9297},
  language     = {eng},
  number       = {6},
  pages        = {2748--2758},
  publisher    = {The American Chemical Society},
  series       = {Macromolecules},
  title        = {Primary Amine-Functional Benzoxazine Monomers and Their Use for Amide-Containing Monomeric Benzoxazines},
  url          = {http://dx.doi.org/10.1021/ma902556k},
  volume       = {43},
  year         = {2010},
}