Synthetic polymers have a key role in modern society as they have allowed for great technological advancement since their discovery. However, the use of fossil-fuel-based raw materials and the pollution derived from plastics accumulation in the environment raised enormous concern, driving research efforts toward the identification of more sustainable alternatives. Bio-based functional molecules susceptible to ring-opening (co)polymerisation [RO(C)OP], such as lactones, cyclic carbonates, and oxiranes, represent an attractive source of monomers for the synthesis of more sustainable polymers. In this review, we describe the main advancement in this research field reported during the last seven years. In particular, we describe the preparation of monomers from (renewable) bio-sources such as sugars, terpenes, fatty acids, and carbon dioxide with a focus on structurally novel substrates. Both metal-mediated and organo-catalytic RO(CO)P methods are described, and the properties of derived functional polymers are discussed when relevant.

/pdf/recent-advances-in-ro-co-p-of-bio-based-monomers-21n1y3kk.pdf

Recent Advances in RO(CO)P of Bio-Based Monomers

The use of neutral donor ligands is an effective strategy to modify catalyst structure and performance in the synthesis of sustainable polymers through the ring-opening polymerization (ROP) of cyclic esters. 

The versatile roles of neutral donor ligands in tuning catalyst performance for the ring-opening polymerization of cyclic esters

A highly efficient late-transition metal based catalytic system of α-diimine FeCl3 for well-controlled ring opening polymerization of a cheap and biobased macrolactone, ethylene brassylate (EB), is described herein. Proceeding via a coordination-insertion mechanism, such a catalytic system is capable of demonstrating unprecedented higher activities than previously reported organocatalysts or main-group metal based catalysts. Moreover, benefiting from the bulky nature of the α-diimine ligands, transesterification side reactions can be greatly suppressed, allowing the polymerization to proceed in a well-controlled living manner, as revealed from detailed kinetic studies. Additionally, such a catalytic system was also workable for ring opening copolymerization of EB and ε-caprolactone (ε-CL), giving the desired random copolymers with various compositions.

Efficient and well-controlled ring opening polymerization of biobased ethylene brassylate by α-diimine FeCl3 catalysts via a coordination-insertion mechanism.

Electron beam induced graft polymerized anti oil-fouling biaxial polypropylene membrane with harsh environment tolerance

Ethylene brassylate is a renewable macrolactone from castor oil that can be polymerized via ring-opening polymerization (ROP) to obtain a fully biosourced biodegradable polyester. ROP mediated by organometallic catalysts leads to high molar mass poly(ethylene brassylate) (PEB). However, the use of metal-free organocatalysis has several advantages, such as the reduction of toxic and expensive metals. In this work, a novel cellulose nanofibril (CNF)/PEB nanocomposite fabrication process by organocatalysis and reactive extrusion (REx) is disclosed. Here, ROP was carried out via solvent-free REx in the presence of CNFs using organic 1,5,7-triazabicyclo[4.4.0]dec-5-ene as a catalyst. Neat or lactate-esterified CNFs (LACNF) were used as initiators to investigate the effect of surface topochemistry on the in situ polymerization and the properties of the nanocomposites. A molar mass of 9 kDa was achieved in the presence of both unmodified and LACNFs with high monomer conversion (>98%) after 30 min reaction in a microcompounder at 130 °C. Tensile analysis showed that both nanofibril types reinforce the matrix and increase its elasticity due to the efficient dispersion obtained through the grafting from polymerization achieved during the REx. Mechanical recycling of the neat polymer and the nanocomposites was proven as a circular solution for the materials' end-of-life and showed that lactate moieties induced some degradation. 

Organo-Mediated Ring-Opening Polymerization of Ethylene Brassylate from Cellulose Nanofibrils in Reactive Extrusion

Sodium complexes bearing cavity-like conformations: a highly active and well-controlled catalytic system for macrolactone homo- and copolymerization

Poly(1-butene) is a kind of unique poly(α-olefin) material that displays exceptional creep resistance and environmental stress cracking resistance, and therefore currently finds wide application in the fields of packaging, films, pipes, etc. However, very few current researchers are paying attention to functional poly(1-butene) despite its great research significance, perhaps due to the general paucity of catalytic systems for synthesizing this material. Therefore, in the present study, we set out to develop an alternative method to prepare polar poly(1-butene)s. Specifically, 1,2-enriched poly(1,3-butadiene), used as a starting material, was partially hydrogenated to afford a quasi-poly(1-butene) polymer containing CC double bonds. These double bonds were further modified by subjecting the quasi-poly(1-butene) polymer to a thiol-ene reaction in the presence of thiol compounds, and a series of polar poly(1-butene)s that bore significantly improved surface properties were obtained. By using hydroxyl-containing thiol compounds, ring-opening polymerization (ROP) of e-caprolactone was further implemented. Here, polar poly(e-caprolactone) was incorporated as side chains, and we were able to control the chain length by adjusting the feeding ratio. The water contact angles of the resultant polymers, i.e., those containing the poly(e-caprolactone) side chains, were as low as 59.4°, indicating a greater hydrophilicity resulting from the incorporation of these side chains.

/pdf/preparation-of-functionalized-poly-1-butene-from-1-2-2jaqeofrbc.pdf

Preparation of functionalized poly(1-butene) from 1,2-polybutadiene via sequential thiol-ene click reaction and ring-opening polymerization

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Sodium complexes bearing cavity-like conformations: a highly active and well-controlled catalytic system for macrolactone homo- and copolymerization

Preparation of functionalized poly(1-butene) from 1,2-polybutadiene via sequential thiol-ene click reaction and ring-opening polymerization