Next Article in Journal
Dielectric Trapping of Biopolymers Translocating through Insulating Membranes
Next Article in Special Issue
A Novel Ziegler–Natta-Type Catalytic System—TiCl4/2,2′-Dimethoxy-1,1′-Binaphthalene/Et3Al2Cl3/Bu2Mg for Production of Ultrahigh Molecular Weight Polyethylene Nascent Reactor Powders, Suitable for Solvent-Free Processing
Previous Article in Journal
Multiscale Modification of Populus cathayana by Alkali Lignin Combined with Heat Treatment
Previous Article in Special Issue
Influences of Fluorine Substituents on Iminopyridine Fe(II)- and Co(II)-Catalyzed Isoprene Polymerization
Article

α,ω-Epoxide, Oxetane, and Dithiocarbonate Telechelic Copolyolefins: Access by Ring-Opening Metathesis/Cross-Metathesis Polymerization (ROMP/CM) of Cycloolefins in the Presence of Functional Symmetric Chain-Transfer Agents

1
Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)—UMR 6226, F-35000 Rennes, France
2
BOSTIK S.A., 253, Avenue du Président Wilson, F-93211 La Plaine Saint-Denis, France
3
BOSTIK, ZAC du Bois de Plaisance, 101, Rue du Champ Cailloux, F-60280 Venette, France
*
Authors to whom correspondence should be addressed.
Polymers 2018, 10(11), 1241; https://doi.org/10.3390/polym10111241
Received: 16 October 2018 / Revised: 3 November 2018 / Accepted: 4 November 2018 / Published: 9 November 2018
(This article belongs to the Special Issue Olefin Polymerization and Polyolefin)
Epoxide- and oxetane-α,ω-telechelic (co)polyolefins have been successfully synthesized by the tandem ring-opening metathesis polymerization (ROMP)/cross-metathesis (CM) of cyclic olefins using Grubbs’ second-generation catalyst (G2) in the presence of a bifunctional symmetric alkene epoxide- or oxetane-functionalized chain-transfer agent (CTA). From cyclooctene (COE), trans,trans,cis-1,5,9-cyclododecatriene (CDT), norbornene (NB), and methyl 5-norbornene-2-carboxylate (NBCOOMe), with bis(oxiran-2-ylmethyl) maleate (CTA 1), bis(oxetane-2-ylmethyl) maleate (CTA 2), or bis(oxetane-2-ylmethyl) (E)-hex-3-enedioate (CTA 3), well-defined α,ω-di(epoxide or oxetane) telechelic PCOEs, P(COE-co-NB or -NBCOOMe)s, and P(NB-co-CDT)s were isolated under mild operating conditions (40 or 60 °C, 24 h). The oxetane CTA 3 and the epoxide CTA 1 were revealed to be significantly more efficient in the CM step than CTA 2, which apparently inhibits the reaction. Quantitative dithiocarbonatation (CS2/LiBr, 40 °C, THF) of an α,ω-di(epoxide) telechelic P(NB-co-CDT) afforded a convenient approach to the analogous α,ω-bis(dithiocarbonate) telechelic P(NB-co-CDT). The nature of the end-capping function of the epoxide/oxetane/dithiocarbonate telechelic P(NB-co-CDT)s did not impact their thermal signature, as measured by DSC. These copolymers also displayed a low viscosity liquid-like behavior and a shear thinning rheological behavior. View Full-Text
Keywords: chain-transfer agent; dithiocarbonate; epoxide; oxetane; functional polyolefin; ring-opening metathesis polymerization; telechelic polymer chain-transfer agent; dithiocarbonate; epoxide; oxetane; functional polyolefin; ring-opening metathesis polymerization; telechelic polymer
Show Figures

Graphical abstract

MDPI and ACS Style

Vanbiervliet, E.; Fouquay, S.; Michaud, G.; Simon, F.; Carpentier, J.-F.; Guillaume, S.M. α,ω-Epoxide, Oxetane, and Dithiocarbonate Telechelic Copolyolefins: Access by Ring-Opening Metathesis/Cross-Metathesis Polymerization (ROMP/CM) of Cycloolefins in the Presence of Functional Symmetric Chain-Transfer Agents. Polymers 2018, 10, 1241. https://doi.org/10.3390/polym10111241

AMA Style

Vanbiervliet E, Fouquay S, Michaud G, Simon F, Carpentier J-F, Guillaume SM. α,ω-Epoxide, Oxetane, and Dithiocarbonate Telechelic Copolyolefins: Access by Ring-Opening Metathesis/Cross-Metathesis Polymerization (ROMP/CM) of Cycloolefins in the Presence of Functional Symmetric Chain-Transfer Agents. Polymers. 2018; 10(11):1241. https://doi.org/10.3390/polym10111241

Chicago/Turabian Style

Vanbiervliet, Elise, Stéphane Fouquay, Guillaume Michaud, Frédéric Simon, Jean-François Carpentier, and Sophie M. Guillaume 2018. "α,ω-Epoxide, Oxetane, and Dithiocarbonate Telechelic Copolyolefins: Access by Ring-Opening Metathesis/Cross-Metathesis Polymerization (ROMP/CM) of Cycloolefins in the Presence of Functional Symmetric Chain-Transfer Agents" Polymers 10, no. 11: 1241. https://doi.org/10.3390/polym10111241

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop