Amine Exchange of Aminoalkylated Phenols as Dynamic Reaction in Benzoxazine/Amine-Based Vitrimers.
amine
aminoalkylated phenol
benzoxazine
reaction mechanism
vitrimer
Journal
Macromolecular rapid communications
ISSN: 1521-3927
Titre abrégé: Macromol Rapid Commun
Pays: Germany
ID NLM: 9888239
Informations de publication
Date de publication:
10 Oct 2024
10 Oct 2024
Historique:
revised:
27
08
2024
received:
08
07
2024
medline:
10
10
2024
pubmed:
10
10
2024
entrez:
10
10
2024
Statut:
aheadofprint
Résumé
Bisfunctional benzoxazine and polyether diamine-based polymers show Arrhenius-like stress-relaxation varying with stoichiometry and polymerization temperatures proving vitrimeric behavior. Molecular structural investigations reveal the presence of different aminoalkylated phenols occurring at varying ratios depending on polymer composition and polymerization conditions. The vitrimeric mechanism is found to involve an amine exchange reaction of aminoalkylated phenols in an equilibrium reaction like a nucleophilic substitution reaction. As determined by molecular studies and dissolution experiments in reactive solvents, aliphatic and aromatic primary as well as aliphatic secondary amines in the polybenzoxazine structure can act as nucleophiles in reaction with electrophilic methylene bridges. Thus, aminoalkylated phenols proved to be a relevant structural motif resulting in a vitrimeric polybenzoxazine due to amine exchange reaction.
Identifiants
pubmed: 39388675
doi: 10.1002/marc.202400557
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2400557Informations de copyright
© 2024 The Author(s). Macromolecular Rapid Communications published by Wiley‐VCH GmbH.
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