Biobased, Creep-Resistant Covalent Adaptable Networks Based on β-Amino Ester Chemistry

Abstract

For this study, creep-resistant covalent adaptable networks were prepared by making use of the reversible β-amino ester chemical platform and starting from biobased raw materials with an overall biobased carbon content of >90%. The investigated materials were synthesized with different cross-linking densities in a solvent-free fashion. The applied building blocks consisted of an easily obtained acrylate, based on a biobased diol, and a commercially available biobased multifunctional amine. Following their synthesis, the materials were investigated with regard to their thermal, thermomechanical, and rheological properties, which were preserved after up to three reprocessing cycles. Moreover, the obtained elastomers showed high thermal stability, in combination with good reprocessability at 180 °C and excellent creep resistance at elevated temperatures of up to 120 °C.

Oxidation of Monoterpenes to Form Diols and Triols: A Versatile Toolbox for Polymer Synthesis

“…[53][54][55] Differently from the previous literature, we now combine our toolbox of terpene-based polyols with the aza-Michael polymerization, a well-known reaction that has been applied to biobased diacrylate monomers to produce degradable polymers. [56] To investigate this, three of the polyols (8, 9, and 12) were first con-verted into their corresponding di-acrylate compounds (see Figure 2) using mild, environmentally benign conditions; the esterification was carried out using acrylic acid, which can be biorenewably resourced, and propyl phosphonic acid (T3P), which promotes ester coupling. T3P produces an environmentally benign, water-soluble triphosphate by-product, which is considerably more sustainable than the chlorinated by-products formed when acryloyl chloride is used.…”

Reprocessable and chemically recyclable poly(acylhydrazone–imine) covalent adaptable networks with enhanced mechanical strength and creep resistance

“…[13][14][15][16]24,[30][31][32] However, current CANs have been found to exhibit limitations in mechanical strength and creep resistance due to the reversible nature of DCBs, which may hinder the development of CAN products for practical usage. 25,[33][34][35] Therefore, it remains a forbidden challenge to develop reprocessable and chemically recyclable CANs with high mechanical strength and creep resistance.…”

Enhanced Viscosity Control in Thermosets Derived from Epoxy and Acrylate Monomers Based on Thermoreversible Aza-Michael Chemistry

“…In comparison to the dissociative furan-maleimide Diels–Alder chemistry, where the adducts lose their cross-linking and thus network connectivity already at lower temperatures (<120 °C), − this recently developed and easily implementable BAE chemistry especially allows to have this cross-linking drop at higher temperatures (>160 °C), making this dissociative chemistry more accessible and attractive for manufacturing approaches . In follow-up studies, we reported biobased BAE networks based on pripol and priamine and also BAE networks that have been combined with the vinylogous urethane associative chemistry . Subsequently, the BAE dynamic chemistry was implemented by Caillol, Ladmiral, and co-workers, where they aimed to speed up the reactivity rates of the corresponding materials by either the incorporation of additional hydroxy groups or fluorine neighboring groups. , Further, Lee et al incorporated this dynamic chemistry in their materials by utilizing BPA-based acrylates and a triamine cross-linker to obtain materials with shape memory and healing properties .…”