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See detailRecent developments in the ring-opening polymerization of epsilon-caprolactone and derivatives initiated by tin(IV) alkoxides
Lecomte, Philippe ULg; Stassin, Fabrice; Jérôme, Robert ULg

in Macromolecular Symposia (2004), 215

The macromolecular engineering of aliphatic polyesters by Ring-Opening Polymerization (ROP) initiated by aluminum alkoxides is now well established. Tin (IV) alkoxides are less popular, mainly because of ... [more ▼]

The macromolecular engineering of aliphatic polyesters by Ring-Opening Polymerization (ROP) initiated by aluminum alkoxides is now well established. Tin (IV) alkoxides are less popular, mainly because of a poorer control of the chain growth. This paper discusses some recent examples from CERM, showing that tin (IV) alkoxides can advantageously replace the aluminum counterparts as ROP initiators. For instance, they can initiate successfully the Ring-Opening Polymerization of α-chloro-ε-caprolactone and dioxepane-2-one. They are also very promising initiators for ROP in supercritical CO2 and for the synthesis of clay/aliphatic polyester nanocomposites. [less ▲]

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See detailRing opening polymerization
Lecomte, Philippe ULg; Jérôme, Robert ULg

in Kroschwitz, Jacqueline (Ed.) Encyclopedia of Polymer Science and Technology, Third Edition (2004)

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See detailRecent progress in the macromolecular engineering of aliphatic polyesters
Jérôme, Robert ULg; Li, Haiying; Rieger, Jutta et al

Conference (2004, July 04)

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See detailRing-opening polymerization of alpha-chloro-epsilon-caprolactone and chemical modification of poly(alpha-chloro-epsilon-caprolactone) by atom transfer radical processes
Lenoir, Sandrine ULg; Riva, Raphaël ULg; Lou, Xudong et al

in Macromolecules (2004), 37(11), 4055-4061

A highly versatile strategy was implemented in order to attach a range of polymer grafts and functional groups along the backbone of poly(epsilon-caprolactone). alpha-Chloro-epsilon-caprolactone ... [more ▼]

A highly versatile strategy was implemented in order to attach a range of polymer grafts and functional groups along the backbone of poly(epsilon-caprolactone). alpha-Chloro-epsilon-caprolactone (alphaClepsilonCL) was first prepared by the Baeyer-Villiger oxidation of alpha-chlorocyclohexanone. This monomer (alpha-Cl-epsilon-CL) was then copolymerized with epsilon-caprolactone in the presence of 2,2-dibutyl-2-stanna-1,3-dioxepane. Finally, the pendant activated chlorides of the copolymer were used to initiate (i) the "grafting from" of poly(methyl methacrylate) by atom transfer radical polymerization and (ii) the grafting of benzoate groups by atom transfer radical addition of 3-butenyl benzoate. [less ▲]

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See detailMacromolecular engineering of aliphatic polyesters
Lecomte, Philippe ULg

Scientific conference (2003, September)

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See detailCharge transfer complex inimer: A facile route to dendritic materials
Wang, Wenxin; Yan, Deyue; Bratton, Daniel et al

in Advanced Materials (2003), 15(16), 1348-1352

A versatile approach to the preparation of hyperbranched polymers, in which an inimer is used to assemble a charge transfer complex (CTC) with conventional vinyl monomers, is reported. A novel ... [more ▼]

A versatile approach to the preparation of hyperbranched polymers, in which an inimer is used to assemble a charge transfer complex (CTC) with conventional vinyl monomers, is reported. A novel hyperbranched fluoro-polymer (see Figure) has been successfully synthesized through the copolymerization of chlorotrifluoroethylene (CTFE) and p-(chloromethyl)styrene (CMS) by atom transfer radical polymerization (ATRP). [less ▲]

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See detailRecent progress in ring-opening of ε-caprolactone and derivatives
Lecomte, Philippe ULg; Jérôme, Robert ULg

Conference (2003, July 02)

This oral communication was presented by Philippe Lecomte

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See detail2-oxepane-1,5-dione: a precursor of a novel class of versatile semicrystalline biodegradable (co)-polyesters
Lecomte, Philippe ULg; Latere Dwan'Isa, Jean-Pierre; Dubois, Philippe et al

Poster (2003, July 01)

2-oxepane-1,5-dione (OPD) was synthesized by Baeyer-Villiger oxidation of 1,4-cyclohexanedione and ring-opening polymerized by 1-phenyl-2-propanol / tin octoate with formation of a semicrystalline ... [more ▼]

2-oxepane-1,5-dione (OPD) was synthesized by Baeyer-Villiger oxidation of 1,4-cyclohexanedione and ring-opening polymerized by 1-phenyl-2-propanol / tin octoate with formation of a semicrystalline polyester of high melting temperature (Tm: 147°C). A crystallographic study showed that the polyester is orthorombic in the P212121 space with two molecules extended along the c-axis as is the case for poly(ε-caprolactone) (PCL). Dibutyltin dimethoxide and 2,2-dibutyl-2-stanna-1,3-dioxepane (DSDOP) proved to be efficient initiators for the random copolymerization of ε-caprolactone (εCL) and OPD. Random distribution of the comonomer units was confirmed by DSC, 1H and 13C NMR analyses. A single Tm was observed, which varies regularly and monotonically with the OPD content as result of a cocrystallisation phenomenon. The single glass transition temperature (Tg) obeys the Fox equation. It is noteworthy that a copolymer containing 30 mol % OPD exhibits a Tm of 90°C. It is stable up to 140°C under nitrogen for one hour, such that processing by extrusion is quite possible. The OPD decomposition is maximum at 223°C for a heating rate of 10°C/min. The mechanism of thermal degradation was investigated and cleared up. The ketone increases the copolymer hydrophilicity and thus sensitivity to hydrolysis. The mechanical properties are quite reminiscent of PCL of comparable molecular weight. Quite interestingly, OPD imparts sensitivity to photo-cross-linking to this novel class of materials. [less ▲]

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See detailHydrolytic and thermal degradation of random copolyesters of epsilon-caprolactone and 2-oxepane-1,5-dione
Dwan'Isa Latere, Jean-Pierre; Lecomte, Philippe ULg; Dubois, Philippe ULg et al

in Macromolecular Chemistry and Physics (2003), 204(9), 1191-1201

The hydrolytic and thermal stability of random copolyesters of epsilon-caprolactone (epsilon-CL) and ca. 30 mol-% 2-oxepane-1,5-dione (OPD) have been investigated. Compared with poly(epsilon-caprolactone ... [more ▼]

The hydrolytic and thermal stability of random copolyesters of epsilon-caprolactone (epsilon-CL) and ca. 30 mol-% 2-oxepane-1,5-dione (OPD) have been investigated. Compared with poly(epsilon-caprolactone) (PCL) of a comparable molecular weight, the hydrolytic degradation of the copolyester is faster in a phosphate buffer (pH = 7.4) at 37°C as confirmed by the time dependence of water absorption, weight loss, melting temperature, and molecular weight. This difference is a result of the higher hydrophilicity imparted to the copolyester by the ketone of the OPD units. The thermal degradation has been studied by thermogravimetric analysis (TGA), (HNMR)-H-1 spectroscopy, and size exclusion chromatography (SEC). The activation energy of the thermal degradation under nitrogen has been found to be lower for the copolyesters than for PCL, which indicates that the OPD co-units have a deleterious effect on the thermal stability of PCL. The thermal degradation primarily occurs by pyrolysis of the ester functions. [less ▲]

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See detailPoly(α-chloro-ε-caprolactone), a new precursor for functionalized and graft polyesters
Riva, Raphaël ULg; Lenoir, Sandrine; Lecomte, Philippe ULg et al

Poster (2003, May 16)

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See detail2-oxepane-1,5-dione: a precursor of a novel class of versatile semicrystalline biodegradable (co)-polyesters
Latere Dwan'Isa, Jean-Pierre; Lecomte, Philippe ULg; Dubois, Philippe et al

Poster (2003, May 16)

2-oxepane-1,5-dione (OPD) was synthesized by Baeyer-Villiger oxidation of 1,4 cyclohexanedione and ring-opening polymerized by 1-phenyl- 2-propanol / tin octoate with formation of a semicrystalline ... [more ▼]

2-oxepane-1,5-dione (OPD) was synthesized by Baeyer-Villiger oxidation of 1,4 cyclohexanedione and ring-opening polymerized by 1-phenyl- 2-propanol / tin octoate with formation of a semicrystalline polyester of high melting temperature (Tm :147°C). Dibutyin dimethoxide and 2,2-dibutyl-2-stanna-1,3-dioxepane (DSDOP) proved to be efficient initiators for the random copolymerization of ε-caprolactone (εCL) and OPD. Random distribution of the comonomer units was confirmed by DSC, 1H and 13C NMR analyses. A single Tm was observed, which varies regularly and monotonically with the OPD content as result of a cocrystallisation phenomenon. The single glass transition temperature (Tg) obeys the Fox equation. It is noteworthy that a copolymer containing 30 mol % OPD exhibits a Tm of 90°C. It is stable up to 140°C under nitrogen for one hour, such that processing by extrusion is quite possible. The OPD decomposition is maximum at 223°C for a heating rate of 10°C/min. The mechanism of thermal degradation was investigated and cleared up. The ketone increases the copolymer hydrophilicity and thus sensitivity to hydrolysis. The mechanical properties are quite reminiscent of PCL of comparable molecular weight. Quite interestingly, OPD imparts sensitivity to photo-cross-linking to this novel class of materials. [less ▲]

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See detailSynthesis of macrocyclic polyesters
Lecomte, Philippe ULg; Jérôme, Robert ULg

Poster (2003, May 16)

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See detailSynthesis and characterization of random copolyesters of epsilon-caprolactone and 2-oxepane-1,5-dione
Latere Dwan'Isa, Jean-Pierre; Lecomte, Philippe ULg; Dubois, Philippe ULg et al

in Macromolecules (2003), 36(8), 2609-2615

2-Oxepane-1,5-dione (OPD) has been synthesized by the Baeyer-Villiger oxidation of 1,4-cyclohexanedione and copolymerized with epsilon-caprolactone. This random copolymerization has been initiated by ... [more ▼]

2-Oxepane-1,5-dione (OPD) has been synthesized by the Baeyer-Villiger oxidation of 1,4-cyclohexanedione and copolymerized with epsilon-caprolactone. This random copolymerization has been initiated by different metal derivatives, i.e., tin octanoate, dibutyltin dimethoxide, and aluminum isopropoxide. Dibutyltin dimethoxide is the preferred initiator, and the course of polymerization is controlled by the competition of the ketone of OPD and the ester of the lactones for coordination to the initiator. Semicrystalline copolymers are formed, whose the randomness has been confirmed by DSC, H-1 NMR, and C-13 NMR analysis. A single melting temperature (Tm) has been observed, which varies regularly and monotonically with the OPD content as result of a cocrystallization phenomenom. The single glass transition temperature (Tg) obeys the Fox equation. [less ▲]

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See detailAmphiphilic copolymers of epsilon-caprolactone and gamma-substituted epsilon-caprolactone. Synthesis and functionalization of poly(D,L-lactide) nanoparticles
Gautier, Sandrine; D'Aloia, Violetta; Halleux, Olivier et al

in Journal of Biomaterials Science. Polymer Edition (2003), 14(1), 63-85

Fully biodegradable and surface-functionalized poly(D,L-lactide) (PLA) nanoparticles have been prepared by a co-precipitation technique. Novel amphiphilic random copolyesters P(CL-co-gamma XCL) were ... [more ▼]

Fully biodegradable and surface-functionalized poly(D,L-lactide) (PLA) nanoparticles have been prepared by a co-precipitation technique. Novel amphiphilic random copolyesters P(CL-co-gamma XCL) were synthesized by controlled copolymerization of epsilon-caprolactone and epsilon-caprolactone substituted in the gamma-position by a hydrophilic X group, where X is either a cationic pyridinium (gamma-Py-CL) or a non-ionic hydroxyl (gamma-OH-CL). Nanoparticles were prepared by co-precipitation of PLA with the P(CL-co-gamma-XCL) copolyester from a DMSO solution. Small amounts of cationic P(CL-co-gamma-Py-CL) copolymers are needed to quantitatively form stable nanoparticles (ca. 10 mg/100 mg PLA), although larger amounts of non-ionic P(CL-co-gamma-OH-CL) copolymers are needed (ges12.5 mg/100 mg PLA). Copolymers with a low degree of polymerization (ca. 40) are more efficient stabilizers, probably because of faster migration towards the nanoparticle-water interface. The nanoparticle diameter decreases with the polymer concentration in DMSO, e.g. from ca. 160 nm (16 mg/ml) to ca. 100 nm (2 mg/ml) for PLA/P(CL-co-gamma-Py-CL) nanoparticles. Migration of the P(CL-co-gamma-XCL) copolyesters to the nanoparticle surface was confirmed by measurement of the zeta potential, i.e. ca. +65 mV for P(CL-co-gamma-Py-CL) and -7 mV for P(CL-co-gamma-OH-CL). The polyamphiphilic copolyesters stabilize PLA nanoparticles by electrostatic or steric repulsions, depending on whether they are charged or not. They also impart functionality and reactivity to the surface, which opens up new opportunities for labelling and targeting purposes. [less ▲]

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See detail2-oxepane-1,5-dione: A precursor of a novel class of versatile semicrystalline biodegradable (Co)polyesters
Latere, Jean-Pierre; Lecomte, Philippe ULg; Dubois, Philippe ULg et al

in Macromolecules (2002), 35(21), 7857-7859

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See detailNovel unsaturated epsilon-caprolactone polymerizable by ring-opening and ring-opening metathesis mechanisms
Lou, Xudong; Detrembleur, Christophe ULg; Lecomte, Philippe ULg et al

in e-Polymers (2002), (34), 1-12

Ring-opening polymerization (ROP) and ring-opening metathesis polymerization (ROMP) of an unsaturated epsilon-caprolactone, 6,7-dihydro-2(3H)-oxepinone (DHO2), are alternative routes to produce ... [more ▼]

Ring-opening polymerization (ROP) and ring-opening metathesis polymerization (ROMP) of an unsaturated epsilon-caprolactone, 6,7-dihydro-2(3H)-oxepinone (DHO2), are alternative routes to produce unsaturated aliphatic polyesters with the same molecular structure. Polymerization of DHO2 initiated by Al isopropoxide in toluene at room temperature or at 0°C proceeds by a coordination-insertion mechanism, although intramolecular transesterification takes place beyond complete monomer conversion. The molecular weight distribution is narrow as long as monomer conversion does not exceed 90%. Ring-opening metathesis polymerization of DHO2 initiated by Schrock's Mo-based catalyst, 1, at 60°C allows higher molecular weight unsaturated polyester to be prepared, even though an intramolecular side reaction also operates. The structure of poly(DHO2) synthesized by ROP and ROMP is the same, as confirmed by 1H, 13C NMR, and FT-IR spectra. Copolymers of DHO2 with norbornene, cis-cyclooctene, and 1,5-cyclooctadiene have been successfully prepared. [less ▲]

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See detailControlled synthesis and chemical modification of unsaturated aliphatic (co)polyesters based on 6,7-dihydro-2(3H)-oxepinone
Lou, Xudong; Detrembleur, Christophe ULg; Lecomte, Philippe ULg et al

in Journal of Polymer Science. Part A, Polymer Chemistry (2002), 40(14), 2286-2297

A pure unsaturated cyclic ester, 6,7-dihydro-2(3H)-oxepinone (DHO2), was prepared by a new synthetic route. The copolymerization of DHO2 with epsilon-caprolactone (CL) was initiated by aluminum ... [more ▼]

A pure unsaturated cyclic ester, 6,7-dihydro-2(3H)-oxepinone (DHO2), was prepared by a new synthetic route. The copolymerization of DHO2 with epsilon-caprolactone (CL) was initiated by aluminum isopropoxide [Al(OiPr)3] at 0 °C as an easy way to produce unsaturated aliphatic polyesters with nonconjugated CC double bonds in a controlled manner. The chain growth was living, as certified by the agreement between the experimental molecular weight at total monomer conversion and the value predicted from the initial monomer/initiator molar ratio. The polydispersity was reasonably low (weight-average molecular weight/number-average molecular weight 1.2). The homopolymerization of DHO2 was, however, not controlled because of fast intramolecular transesterification. Copolymers of DHO2 and CL were quantitatively oxidized with the formation of epoxides containing chains. The extent of the epoxidation allowed the thermal properties and thermal stability of the copolyesters to be modulated. The epoxidized copolyesters were successfully converted into thioaminated chains, which were then quaternized into polycations. No degradation occurred during the chemical modification. [less ▲]

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