Abstract
A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (Tg) than those prepared from their primary diol equivalents. Two methods of polymerisation were investigated, the first employing activation of the aromatic diacids via the corresponding diacid chlorides and the second using a transesterification procedure. Longer chain diols were found to be more reactive than the shorter chain alternatives, generally giving rise to higher molecular weight polymers, an effect shown to be most pronounced when using the transesterification route. Finally, novel diesters with high degrees of branching in their hydrocarbon chains are introduced as potential monomers for possible low surface energy materials applications.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 61-77 |
| Number of pages | 17 |
| Journal | Faraday Discussions |
| Volume | 202 |
| DOIs | |
| State | Published - 2017 |
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ASJC Scopus subject areas
- Medicine(all)
- Physical and Theoretical Chemistry
Cite this
New bio-based monomers : Tuneable polyester properties using branched diols from biomass. / Arnaud, Sacha Pérocheau; Wu, Linglin; Wong Chang, Maria Angelica; Comerford, James W.; Farmer, Thomas J.; Schmid, Maximilian; Chang, Fei; Li, Zheng; Mascal, Mark.
In: Faraday Discussions, Vol. 202, 2017, p. 61-77.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - New bio-based monomers
T2 - Tuneable polyester properties using branched diols from biomass
AU - Arnaud, Sacha Pérocheau
AU - Wu, Linglin
AU - Wong Chang, Maria Angelica
AU - Comerford, James W.
AU - Farmer, Thomas J.
AU - Schmid, Maximilian
AU - Chang, Fei
AU - Li, Zheng
AU - Mascal, Mark
PY - 2017
Y1 - 2017
N2 - A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (Tg) than those prepared from their primary diol equivalents. Two methods of polymerisation were investigated, the first employing activation of the aromatic diacids via the corresponding diacid chlorides and the second using a transesterification procedure. Longer chain diols were found to be more reactive than the shorter chain alternatives, generally giving rise to higher molecular weight polymers, an effect shown to be most pronounced when using the transesterification route. Finally, novel diesters with high degrees of branching in their hydrocarbon chains are introduced as potential monomers for possible low surface energy materials applications.
AB - A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (Tg) than those prepared from their primary diol equivalents. Two methods of polymerisation were investigated, the first employing activation of the aromatic diacids via the corresponding diacid chlorides and the second using a transesterification procedure. Longer chain diols were found to be more reactive than the shorter chain alternatives, generally giving rise to higher molecular weight polymers, an effect shown to be most pronounced when using the transesterification route. Finally, novel diesters with high degrees of branching in their hydrocarbon chains are introduced as potential monomers for possible low surface energy materials applications.
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U2 - 10.1039/c7fd00057j
DO - 10.1039/c7fd00057j
M3 - Article
VL - 202
SP - 61
EP - 77
JO - Faraday Discussions of the Chemical Society
JF - Faraday Discussions of the Chemical Society
SN - 1364-5498
ER -