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Renewable Beta‐Elemene Based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s
Author(s) -
Maquilón Cristina,
Brandolese Arianna,
Alter Christian,
Hövelmann Claas H.,
Della Monica Francesco,
Kleij Arjan W.
Publication year - 2022
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202201123
Subject(s) - isocyanate , cycloaddition , chemistry , halide , salt (chemistry) , organic chemistry , polymer chemistry , catalysis , polyurethane
Abstract Conversion of β‐elemene into new β‐elemene dicarbonates through epoxidation and halide salt‐catalyzed CO 2 cycloaddition reactions is reported. Step‐growth polyaddition of this dicarbonate to five different, commercial diamines was investigated under neat conditions at 150 °C yielding non‐isocyanate‐based low molecular weight oligo(hydroxyurethane)s with 1.3≤ M n ≤6.3 kDa and 1.3≤ Ð ≤2.1, and with glass transition temperatures ranging from −59 to 84 °C. The preparation of one selected polyhydroxyurethane material, obtained in the presence of Jeffamine® D‐2010 was scaled‐up to 43 g. The latter, when combined in a formulation using Irgacure® 2100 and Laromer® LR 9000 allowed the preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanes towards the preparation of commercially relevant materials.