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High Glass Transition Temperature Renewable Polymers via Biginelli Multicomponent Polymerization
Author(s) -
Boukis Andreas C.,
Llevot Audrey,
Meier Michael A. R.
Publication year - 2016
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201500717
Subject(s) - glass transition , condensation polymer , monomer , polymer , thermal stability , polymerization , molar mass , materials science , polymer chemistry , organic chemistry , chemical engineering , chemistry , engineering
A novel and straightforward one‐pot multicomponent polycondensation method was established in this work. The Biginelli reaction is a versatile multicomponent reaction of an aldehyde, a β‐ketoester (acetoacetate) and urea, which can all be obtained from renewable resources, yielding diversely substituted 3,4‐dihydropyrimidin‐2(1H)‐ones (DHMPs). In this study, renewable diacetoacetate monomers with different spacer chain lengths (C3, C6, C10, C20) were prepared via simple transesterification of renewable diols and commercial acetoacetates. The diacetoacetate monomers were then reacted with renewable dialdehydes, i.e., terephthalaldehyde and divanillin in a Biginelli type step‐growth polymerization. The obtained DHMP polymers (polyDHMPs) displayed high molar masses, high glass transition temperatures ( T g ) up to 203 °C and good thermal stability ( T d5% ) of 280 °C. The T g of the polyDHMPs could be tuned by variation of the structure of the dialdehyde or the diacetoacetate component.