Copolymerization of e-caprolactone and methyl methacrylate with (1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phophoranylidenamino]-2Λ5,Λ5-catenadi(phosphazene) (t-BuP4) as the catalyst has been studied. Nuclear magnetic resonance (NMR) and differential scanning calorimetry (DSC) measurements indicate that the cyclic ester and vinyl monomer form a random copolymer. Thermogravimetric analysis (TGA) measurements demonstrate that such a random copolymer exhibits a decomposition temperature higher than those of the corresponding homopolymers. The present study reveals a “hybrid copolymerization” i.e., a combination of vinyl polymerization and ring-opening polymerization, which makes the incorporation of cyclic and vinyl monomers into the same polymer chain possible. Hybrid copolymerization is expected to produce a number of new interesting polymers.

Hybrid Copolymerization of ε-Caprolactone and Methyl Methacrylate

Triggered by environmental concerns and the rising demands for metal-free polymers in e.g. bio-related and microelectronic applications, studies on organocatalytic polymerization have been launched and developed unprecedentedly during the last 15 years. A wide range of organic molecules are now available in polymer chemists' toolbox to choose from as catalysts for polymerization of (hetero) cyclic and polar vinyl monomers. Apart from the intrinsic merits such as lower toxicity and better solubility compared with (transition) metal catalysts/initiators, organocatalysts have also shown, in many cases, excellence to achieve high polymerization rates and/or good control (selectivity). In addition, particular natures and catalytic/activating mechanisms of organocatalysts have led to new opportunities for rational design and efficient synthesis of macromolecular architectures, i.e. chain structures, topological structures and functionalities. This mini-review is specially themed on pathways to construct copolymer chain structures by organocatalytic copolymerization of mixed type monomers (comonomers bearing different polymerizing moieties) and will be sectioned by different comonomer combinations, including cyclic monoesters of different sizes, cyclic monoesters and lactides, cyclic esters and cyclic carbonates or epoxides, heterocycles and vinyl monomers.

Organocatalytic copolymerization of mixed type monomers

Epoxides bearing fluorine (F)-containing substituents on ethylene oxide were polymerized under mild conditions to give regioregular polyethers. To alleviate the electron-withdrawing effect of fluor...

Regioregular Polymerization of Fluorine-Containing Epoxides

Frequency control of crossover reactions in concurrent cationic vinyl-addition and ring-opening copolymerization of vinyl ethers and oxiranes: specific roles of weak Lewis bases and solvent polarity

Cationic terpolymerization of an alkyl vinyl ether (VE) with oxetane and methyl ethyl ketone (MEK) proceeded via concurrent vinyl-addition, ring-opening, and carbonyl-addition mechanisms. Highly selective crossover reactions occurred in a one-way cycle, resulting in the generation of multiblock polymers with constitutional repeating units comprising a poly(VE) block, a polyoxetane block, and a single MEK unit. The ketone efficiently functioned as a non-homopolymerizable monomer, which reacted with the oxetane-derived oxonium ion to generate an alkoxy group-adjacent carbocation or an oxocarbenium ion. Furthermore, the resulting carbocation allowed to react with only VEs. The polymerization, which was induced with an initiating system of Ph3C+PF6–, 2,6-di-tert-butylpyridine, and 1,4-dioxane, was partly mediated by long-lived propagating species. NMR analysis of the chain end structures revealed that mono- and difluorophosphate moieties generated via the hydrolysis of PF6– were partially responsible for the ...

Cationic Terpolymerization of Vinyl Ethers, Oxetane, and Ketones via Concurrent Vinyl-Addition, Ring-Opening, and Carbonyl-Addition Mechanisms: Multiblock Polymer Synthesis and Mechanistic Investigation

Novel copolymers consisting of 3,3,3-trifluoro-1,2-epoxypropane (TFEP) and N-phenylmaleimide (PMI) units were prepared by the copolymerization of TFEP with PMI initiated with an organozinc compound. Using [Zn(OCH3)2 · (C2H5ZnOCH3)4] as an initiator, the copolymer chains consisted mainly of TFEP-TFEP sequences. The TFEP-PMI sequence content in the copolymer chains was small. On the other hand, using (C2H5ZnOCH3)4 as an initiator, only low molecular weight copolymers were formed. Those copolymers were suggested to have block structure, poly(TFEP)-block-poly(PMI), by the 19F NMR analysis. The copolymers showed higher thermostability than poly-(TFEP).

Copolymerization of 3,3,3‐trifluoro‐1,2‐epoxypropane with N‐phenylmaleimide using organozinc initiators

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Copolymerization of 3,3,3‐trifluoro‐1,2‐epoxypropane with N‐phenylmaleimide using organozinc initiators