TY - JOUR
T1 - New Bio-Polyamides from Terpenes
T2 - α-Pinene and (+)-3-Carene as Valuable Resources for Lactam Production
AU - Stockmann, Paul N.
AU - Pastoetter, Dominik L.
AU - Woelbing, Marion
AU - Falcke, Claudia
AU - Winnacker, Malte
AU - Strittmatter, Harald
AU - Sieber, Volker
N1 - Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/6
Y1 - 2019/6
N2 - The synthesis and polymerization of two β-lactams and two ε-lactams derived from the terpenes α-pinene and (+)-3-carene are reported. The new biopolymers can be considered as polyamide 2 (PA2) and polyamide 6 (PA6)-types with aliphatic stereoregular side chains, which lead to remarkable new properties. The macromolecules are investigated by gel permeation chromatography (GPC), nuclear magnetic resonance (NMR), differential scanning calorimetry (DSC), and infrared (IR). The (+)-3-carene-derived PA6-type is of particular interest, since it reaches a molecular weight of over 30 kDa, which is the highest value for lactam-based polyamides derived from terpenes reported to date. Additionally, a glass transition temperature (Tg) of 120 °C is observed, surpassing the glass transition temperature of PA6 by 60 °C. The absence of a melting point (Tm) indicates high amorphicity, another novelty for terpene-based polyamides, which might give transparent bio-polyamides access to new fields of application.
AB - The synthesis and polymerization of two β-lactams and two ε-lactams derived from the terpenes α-pinene and (+)-3-carene are reported. The new biopolymers can be considered as polyamide 2 (PA2) and polyamide 6 (PA6)-types with aliphatic stereoregular side chains, which lead to remarkable new properties. The macromolecules are investigated by gel permeation chromatography (GPC), nuclear magnetic resonance (NMR), differential scanning calorimetry (DSC), and infrared (IR). The (+)-3-carene-derived PA6-type is of particular interest, since it reaches a molecular weight of over 30 kDa, which is the highest value for lactam-based polyamides derived from terpenes reported to date. Additionally, a glass transition temperature (Tg) of 120 °C is observed, surpassing the glass transition temperature of PA6 by 60 °C. The absence of a melting point (Tm) indicates high amorphicity, another novelty for terpene-based polyamides, which might give transparent bio-polyamides access to new fields of application.
KW - amorphicity
KW - bio-based
KW - polyamides
KW - ring-opening polymerization
KW - terpenes
UR - http://www.scopus.com/inward/record.url?scp=85066815871&partnerID=8YFLogxK
U2 - 10.1002/marc.201800903
DO - 10.1002/marc.201800903
M3 - Article
C2 - 30892749
AN - SCOPUS:85066815871
SN - 1022-1336
VL - 40
JO - Macromolecular Rapid Communications
JF - Macromolecular Rapid Communications
IS - 11
M1 - 1800903
ER -