1. Fabricating a Repairable, Recyclable, Imine-based Dynamic Covalent Thermosetting Resin with Excellent Water Resistance by Introducing Dynamic Covalent Oxime Bonds
Guanglong Li, Xuhui Zhang, Shuobing Yang, Ting Li, Yang Wang, Mingqing Chen, Weifu Dong ChemSusChem. 2021 Oct 5;14(19):4340-4348. doi: 10.1002/cssc.202101408. Epub 2021 Sep 8.
The sustainable production of adaptive, recyclable and imine-based dynamic covalent thermosetting resins (DCTRs) presents an opportunity for polymer scientists to address the prevalent environmental and energy concerns associated with current petroleum-based plastics. However, the imine-based DCTRs easily decompose in the presence of water, which can weaken the mechanical properties in imine-based polymers. In this study, we designed oxime-imine DCTRs that are stable in the presence of water and exhibit good mechanical properties. In the presence of one kind of amino group catalyst, the oxime-imine DCTRs could be completely recycled. Additionally, these well-designed oxime-imine DCTRs have good mechanical properties, high glass transition temperatures (166 °C), and good thermal stabilities. Taken together, this work offers a sustainable solution for the design and manufacture of high-value degradable materials intended for applications in which recyclability and reusability are indispensable.
2. Utilization of Waste Amine-Oxime (WAO) Resin to Generate Carbon by Microwave and Its Removal of Pb(II) in Water
Chunlin He, Yun Liu, Chunhui Zheng, Yanming Jiang, Yan Liao, Jiaxin Huang, Toyohisa Fujita, Yuezhou Wei, Shaojian Ma Toxics. 2022 Aug 23;10(9):489. doi: 10.3390/toxics10090489.
Utilising waste amine-oxime (WAO) resin through microwave semi-carbonization, a carbon adsorbent (CA) was obtained to remove Pb(II). After microwave treatment, the pore size of the skeleton structure, three-dimensional porous network, and lamellar pore structure of WAO was improved. The distribution coefficient (Kd) of Pb(II) onto CA is 620 mL/g, and the maximum adsorption capacity of Pb(II) is 82.67 mg/g after 20 min of WAO microwave treatment. The adsorption kinetics and adsorption isotherms conform to the quasi-second-order kinetic equation and Langmuir adsorption isotherm model, respectively. The surface of MT-WAO is negatively charged and the adsorption mechanism is mainly electrostatic interaction. Pb(II) elution in hydrochloric acid solution is more than 98%, and its recovery is high at 318 K and for 1 h.
3. Synthesis of C-terminal glycopeptides via oxime resin aminolysis
Thomas Tremblay, Gabrielle Robert-Scott, Christopher Bérubé, Antoine Carpentier, Normand Voyer, Denis Giguère Chem Commun (Camb). 2019 Nov 12;55(91):13741-13744. doi: 10.1039/c9cc07481c.
Natural glycopeptides have been shown to possess interesting biological activities. In this work, we have developed a general solid-phase approach to C-terminal glycopeptides. Taking advantage of oxime resin ester bond nucleophile susceptibility, we optimised the nucleophilic cleavage step with glycosylamines and demonstrated the generality and scope of this method. In addition, this reaction has high functional group tolerance and can be used for the preparation of longer C-terminal glycopeptides, demonstrated with the synthesis of a glycododecapeptide in one single step. The results pave the way to access efficiently novel medically relevant compounds.
