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See detailPrecision synthesis of poly(ionic liquid)-based block copolymers by cobalt-mediated radical polymerization and preliminary study of their self-assembling properties
Coupillaud, Paul; Fèvre, Maréva; Wirotius, Anne-Laure et al

in Macromolecular Rapid Communications (2014), 35(4), 422-430

A poly(ionic liquid)-based block copolymer (PIL BCP), namely, poly(vinyl acetate)-b-poly(N-vinyl-3-butylimidazolium bromide), PVAc-b-PVBuImBr, is synthesized by sequential cobalt-mediated radical ... [more ▼]

A poly(ionic liquid)-based block copolymer (PIL BCP), namely, poly(vinyl acetate)-b-poly(N-vinyl-3-butylimidazolium bromide), PVAc-b-PVBuImBr, is synthesized by sequential cobalt-mediated radical polymerization (CMRP). A PVAc precursor is first prepared at 30 °C in bulk by CMRP of VAc, using bis(acetylacetonato)cobalt(II), Co(acac)2, and a radical source (V-70). Growth of PVBuImBr from PVAc-Co(acac)2 is accomplished by CMRP in DMF/MeOH (2:1, v/v). This PIL BCP self-assembles in the sub-micron size range into aggregated core–shell micelles in THF, whereas polymeric vesicles are observed in water, as evidenced by dynamic light scattering (DLS) and transmission electron microscopy (TEM). Thin-solid sample cut from raw materials analyzed by TEM shows an ordered lamellar organization by temperature-dependent synchrotron small-angle X-ray scattering (SAXS). Anion exchange can be accomplished to achieve the corresponding PIL BCP with bis(trifluorosulfonyl)imide (Tf2N−) anions, which also gives rise to an ordered lamellar phase in bulk samples. A complete suppression of SAXS second-order reflection suggests that this compound has a symmetric volume fraction (f ≈ 0.5). SAXS characterization of both di- and triblock PIL BCP analogues previously reported also shows a lamellar phase of very similar behavior, with only an increase of the period by about 8% at 60 °C. [less ▲]

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See detailStructure and properties of a semifluorinated diblock copolymer modified epoxy blend
Ocando, Connie; Serrano, Elena; Tercjak, Agnieszka et al

in Macromolecules (2007), 40(11), 4068-4074

Novel nanostructured thermosetting materials have been prepared by modification of an epoxy resin with a semifluorinated diblock copolymer, poly(heptadecafluorodecyl acrylate)-b-poly(caprolactone), PaF-b ... [more ▼]

Novel nanostructured thermosetting materials have been prepared by modification of an epoxy resin with a semifluorinated diblock copolymer, poly(heptadecafluorodecyl acrylate)-b-poly(caprolactone), PaF-b-PCL. In a first step, the phase behavior and linear viscoelasticity of PaF-b-PCL were investigated. According to the segregation regime, no order-order transitions were detected, being the order-disorder transition temperature beyond the degradation temperature. Atomic force microscopy (AFM) images of the block copolymer after different thermal treatments revealed that self-assembly takes place into spherical nanodomains, which is consistent with the copolymer composition. This block copolymer was further used to prepare a nanostructured thermoset blend with an epoxy resin. DSC and DMA analysis reveals microphase separation of PaF block from the epoxy-rich phase after curing. The PaF block self-assembled into wormlike and spherical micelles in the thermoset system. This nanostructured blend presented unique surface properties showing high hydrophobicity (upsilon = 109 degrees) and low surface energy (17 mN/m). [less ▲]

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See detailNew Functional Aliphatic Polyesters by Chemical Modification of Copolymers of ε-Caprolactone with γ-(2-Bromo-2-methylpropionate)- ε-caprolactone, γ-Bromo- ε-caprolactone, and a Mixture of β-and γ-Ene- ε-caprolactone
Detrembleur, Christophe ULg; Mazza, Michaël; Lou, Xudong et al

in Macromolecules (2000), 33(17), 7751-7760

New functional aliphatic polyesters were prepared by chemical modification of brominated copolyesters. Poly(epsilon-caprolactone)-co-poly(gamma-(2-bromo-2-methylpropionate)-epsilon-caprolactone) copolymer ... [more ▼]

New functional aliphatic polyesters were prepared by chemical modification of brominated copolyesters. Poly(epsilon-caprolactone)-co-poly(gamma-(2-bromo-2-methylpropionate)-epsilon-caprolactone) copolymer was prepared and successfully converted into copolyester bearing methacrylate double bonds by dehydrohalogenation of the pendant tertiary alkyl bromides, thus leading to cross-linkable polyester. The tertiary alkyl bromide groups of the original copolyester were also quaternized by reaction with pyridine, although some side reactions occurred which Limited the reaction yield. Nevertheless, quaternization of the bromide groups of the poly(epsilon-caprolactone)-co-poly(gamma-bromo-epsilon-caprolactone) copolymer proved to be quantitative and to occur without degradation of the polyester chains. This general strategy paves the way to either amphiphilic copolyesters or water-soluble polyesters. The poly(epsilon -caprolactone)-co-poly(gamma -bromo-epsilon-caprolactone) lactone) copolymer was also quantitatively converted into unsaturated copolyester by dehydrohalogenation with formation of double bonds including acrylic-type double bonds. As an alternative, gamma-bromo-epsilon-caprolactone was first dehydrohalogenated, and the unsaturated cyclic monomer was copolymerized with epsilon-caprolactone. Finally, the nonconjugated double bonds of the copolyesters were oxidized into epoxides, except for the acrylic-type unsaturations which remained unchanged. [less ▲]

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See detailFirst example of an unsymmetrical difunctional monomer polymerizable by two living/controlled methods
Mecerreyes, David; Humes, J.; Miller, R. D. et al

in Macromolecular Rapid Communications (2000), 21(11), 779-784

In this paper the synthesis and (co)polymerizations of 4-(acryloyloxy)-epsilon-caprolactone are reported. This new monomer can be polymerized in a living/controlled way by two different polymerization ... [more ▼]

In this paper the synthesis and (co)polymerizations of 4-(acryloyloxy)-epsilon-caprolactone are reported. This new monomer can be polymerized in a living/controlled way by two different polymerization mechanisms: atom transfer radical polymerization (ATRP) and ring-opening polymerization (ROP). ATRP, which was carried out at 90 degrees C using NiBr2(PPh3)(2), leads to new polyacrylates containing pendant caprolactone functionalities with controlled molecular weights and narrow polydispersities (M-w/M(p)similar to 1.1). Alternatively, ROP of this functional epsilon-caprolactone bearing a pendant acrylate functionality leads to new poly(4-(acryloyloxy) caprolactone) as well as random copolymers when epsilon-caprolactone and L,L-lactide are added as comonomers. The (co)polymerizations were carried out using either (Al((OPr)-Pr-i)(3) in toluene at 25 degrees C or Sn(Oct)(2) as a catalyst at 110 degrees C producing (co)polymers with controlled molecular weights and narrow polydispersities (M-w/M(n)similar to 1.2). As a potential application, the introduction of acrylate pendant groups into the polyesters facilitated the preparation of cross-linked biodegradable materials either thermally or by irradiation with ultraviolet light radical curing. [less ▲]

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See detailRing-opening polymerization of 6-hydroxynon-8-enoic acid lactone : Novel biodegradable copolymers containing allyl pendent groups
Mecerreyes, David; Miller, Robert D.; Hedrick, James L. et al

in Journal of Polymer Science. Part A, Polymer Chemistry (2000), 38(5), 870-875

This article reports the synthesis and copolymerization of 6-hydroxynon-8-enoic acid lactone. The ring-opening polymerization of this lactone-type monomer bearing a pendant allyl group led to new ... [more ▼]

This article reports the synthesis and copolymerization of 6-hydroxynon-8-enoic acid lactone. The ring-opening polymerization of this lactone-type monomer bearing a pendant allyl group led to new homopolymers and random copolymers with -caprolactone and L,L-lactide. The copolymerizations were carried out at 110 °C with Sn(Oct)2 as a catalyst. The introduction of unsaturations into the aliphatic polyester permitted us to carry out different chemical transformations on this family of polymers. For example, this article reports the bromination, epoxidation, and hydrosylilation of the allyl group in the new polyester copolymers. [less ▲]

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See detailRing-Opening Polymerization of γ-bromo-ε-caprolactone : A novel route to functionalized aliphatic polyesters
Detrembleur, Christophe ULg; Mazza, Michaël; Halleux, Olivier et al

in Macromolecules (2000), 33(1), 14-18

The synthesis, characterization, and polymerization of a new cyclic ester, gamma-bromo-epsilon-caprolactone (gamma-BrCL), are reported. The ring-opening polymerization (ROP) of this new monomer initiated ... [more ▼]

The synthesis, characterization, and polymerization of a new cyclic ester, gamma-bromo-epsilon-caprolactone (gamma-BrCL), are reported. The ring-opening polymerization (ROP) of this new monomer initiated from Al((OPr)-Pr-i)(3) as initiator in toluene at 0 degrees C was found to be living and proceeds by a coordination-insertion mechanism. Random and block copolymerizations of this gamma-BrCL with epsilon-caprolactone (epsilon-CL) were also found to be living as evidenced by the experimental molecular weight which is consistent with that expected from the monomer to initiator molar ratio, the narrow polydispersity, and the good agreement between the comonomers molar fraction in the comonomer feed and the copolymer. The thermal transitions (Tg and Tm) in the epsilon-CL/gamma-Br-CL random copolymers depend strongly on the gamma-BrCL content. Increasing the gamma BrCL content in the copolymer [F(BrCL)] increased the Tg of the copolymer from -61 degrees C for poly(epsilon-caprolactone) to -16.5 degrees C for the poly( gamma-BrCL) homopolymer but decreased the Tm of the PCL to contents of similar to 30 mol % of gamma BrCL [F(BrCL) =0.3]Beyond this value, the copolymers were found to be amorphous and exist as viscous liquids. [less ▲]

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See detailFrom living to controlled aluminium alkoxide mediated ring-opening polymerization of (di)lactones, a powerful tool for the macromolecular engineering of aliphatic polyesters
Mecerreyes, David; Jérôme, Robert ULg

in Macromolecular Chemistry and Physics (1999), 200(12), 2581-2590

The aluminium alkoxide mediated ring-opening polymerization of (di)lactones offers a great versatility to the point where the main situations covered by the definition of living and controlled ... [more ▼]

The aluminium alkoxide mediated ring-opening polymerization of (di)lactones offers a great versatility to the point where the main situations covered by the definition of living and controlled polymerizations can be illustrated. Furthermore, substitution of a coordination-insertion mechanism for the traditional anionic polymerization of these monomers results in species of lower reactivity and in a kinetic control of the polyaddition reaction. This control, combined with the use of Al alkoxides of different structures and functionalities, has opened the way to the macromolecular design of a family of biocompatible and biodegradable polyesters, e.g., controlled synthesis of telechelic polymers, block and graft copolymers, and polymers of various molecular architectures. These polymers can be used as such, or as building parts of more sophisticated polymeric assemblies. [less ▲]

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See detailRing-opening metathesis polymerization of new alpha-norbornenyl poly(epsilon-caprolactone) macromonomers
Mecerreyes, David; Dahan, Dahan; Lecomte, Philippe ULg et al

in Journal of Polymer Science. Part A, Polymer Chemistry (1999), 37(14), 2447-2455

Poly(epsilon-caprolactone) (PCL) macromonomers capped by a polymerizable norbornene end-group have been synthesized and (co)polymerized by ring-opening metathesis with formation of graft copolymers and ... [more ▼]

Poly(epsilon-caprolactone) (PCL) macromonomers capped by a polymerizable norbornene end-group have been synthesized and (co)polymerized by ring-opening metathesis with formation of graft copolymers and polymacromonomers. -Norbornenyl PCL macromonomers have been synthesized by ring opening polymerization (ROP) of epsilon-caprolactone (CL) initiated by 2-diethylaluminoxymethyl-5-norbornene. Copolymerization of these PCL macromonomers with norbornene and polymerizable derivatives has been catalyzed by the [RuCl2(p-cymene)]2 PCy3/(trimethylsilyl)diazomethane complex yielding a series of poly(norbornene)-graft-poly(epsilon-caprolactone) copolymers. These new graft copolymers have been characterized by a set of analytical methods, i.e., SEC, 1H-NMR, FTIR, DSC, and TGA. Furthermore, PCL macromonomers have been polymerized into high molecular weight comb chains of narrow molecular weight distribution (Mw/Mn = 1.10) within high yields (90%). [less ▲]

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See detailSynthesis of dendritic-linear block copolymers by living ring-opening polymerization of lactones and lactides using dendritic initiators
Mecerreyes, David; Dubois, Philippe ULg; Jérôme, Robert ULg et al

in Journal of Polymer Science. Part A, Polymer Chemistry (1999), 37(13), 1923-1930

Polyether dendrons have been successfully used as macroinitiators for the living ring-opening polymerization (ROP) of lactones and lactides. A hydroxyl group located at the focal point of dendrimers of ... [more ▼]

Polyether dendrons have been successfully used as macroinitiators for the living ring-opening polymerization (ROP) of lactones and lactides. A hydroxyl group located at the focal point of dendrimers of different generations was transformed into diethyl aluminum alkoxides by reaction with triethyl aluminum. The dendritic aluminum alkoxides proved to be efficient macroinitiators for the living ROP of -caprolactone (CL), 1,4,8-trioxa(4,6)spiro[9]undecanone (TOSUO), D,L- and L,L-lactide. Formation of these block copolymers of unusual macromolecular architecture was supported by size exclusion chromatography and spectroscopy. The versatility of this synthetic approach allowed -functional dendrimer block-polyesters, such as macromonomer, and macromolecules with novel architectures, to be prepared. [less ▲]

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See detailSynthesis of polynorbornene grafted with poly(ε-caprolactone) by sequential controlled ring opening polymerization
Lecomte, Philippe ULg; Mecerreyes, David; Dubois, Philippe et al

Poster (1999, April 12)

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See detailSynthesis of well-defined poly(alkyl methacrylate)-graft-polylactone by sequential living polymerization
Mecerreyes, David; Dubois, Philippe ULg; Jérôme, Robert ULg et al

in Macromolecular Chemistry and Physics (1999), 200(1), 156-165

A novel combination of living polymerization reactions has been proposed for the controlled synthesis of poly(alkyl methacrylate)-graft-polylactones. This strategy relies upon the sequential living ... [more ▼]

A novel combination of living polymerization reactions has been proposed for the controlled synthesis of poly(alkyl methacrylate)-graft-polylactones. This strategy relies upon the sequential living polymerization of alkyl methacrylates and aliphatic lactones, with an intermediate chemical transformation for shifting from the first mechanism to the second one. In the first step, an alkyl methacrylate (methyl and butyl) is copolymerized with 2-trimethylsiloxyethyl methacrylate (TMSEMA). This living anionic polymerization is initiated with diphenylhexyllithium( DPHLi) in the presence of a μ-ligand, lithium chloride, in THF at - 78 °C. The trimethylsiloxy groups are then hydrolyzed with release of hydroxyl groups which are reacted with triethylaluminum in order to form a multifunctional macroinitiator of the Al alkoxide type. The second step consists of the ring opening polymerization (ROP) of aliphatic lactones (ε-caprolactone, J-valerolactone and 1,4,8-trioxaspiro[4.6]-9-undecanone (TOSUO)) with the formation of novel graft copolymers. As a result of the livingness of both the anionic and the ROP polymerization steps, the molecular weight of both the main backbone and the grafts is predictable, the apparent polydispersity is narrow ( from 1.05 to 1.30) and the grafting density can be controlled being dependent on the distribution of the hydroxyl groups within the precursor backbone. [less ▲]

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See detailNovel macromolecular architectures based on aliphatic polyesters: relevance of the "coordination-insertion" ring-opening polymerization
Mecerreyes, David; Jérôme, Robert ULg; Dubois, Philippe ULg

in Advances in Polymer Science (1999), 147

Recent developments in the macromolecular engineering of aliphatic polyesters have been overviewed. First, aluminum alkoxides mediated living ring opening polymerization (ROP) of cyclic (di)esters, i.e ... [more ▼]

Recent developments in the macromolecular engineering of aliphatic polyesters have been overviewed. First, aluminum alkoxides mediated living ring opening polymerization (ROP) of cyclic (di)esters, i.e., lactones, lactides, glycolide, is introduced. An insight into this so-called "coordination-insertion" mechanism and the ability of this living polymerization process to prepare well-defined homopolymers, telechelic polymers, random and block copolymers is then discussed. In the second part, the combination of the living ROP of (di)lac-tones with other well-controlled polymerization mechanisms such as anionic, cationic, free radical, and metathesis polyadditions of unsaturated comonomers, as well as polyconden-sations, is reported with special emphasis on the design of new and well-tailored macromolecular architectures. As a result of the above synthetic breakthrough, a variety of novel materials have been developed with versatile applications in very different fields such as biomedical and microelectronics. [less ▲]

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See detailDendrimer-like star block and amphiphilic copolymers by combination of ring opening and atom transfer radical polymerization
Hedrick, James L.; Trollsas, Mikael; Hawker, Craig Jon et al

in Macromolecules (1998), 31(25), 8691-8705

A new type of macromolecular architecture, denoted as dendrimer-like star block copolymers, is reported. These block copolymers are described by a radial geometry where the different generations or layers ... [more ▼]

A new type of macromolecular architecture, denoted as dendrimer-like star block copolymers, is reported. These block copolymers are described by a radial geometry where the different generations or layers are comprised of high molecular weight polymer emanating from a central core. A hexahydroxyl functional core was used as an initiator for the “living” ring opening polymerization (ROP) of ε-caprolactone producing a hydroxyl terminated six arm star polymer with controlled molecular weight and narrow polydispersities (PD < 1.1). Capping these chain ends with dendrons containing activated bromide moieties produced “macro-initiators” for atom transfer radical polymerization (ATRP). Methyl methacrylate was polymerized from these “macro-initiators” in the presence of an organometallic promoter to produce the requisite dendrimer-like star polymers. High molecular weight was obtained with low polydispersities (<1.2). Alternatively, amphiphilic character could be introduced by designing the different layers or generations to be either hydrophobic or hydrophilic. For example, methyl methacrylate (MMA) with either hydroxyethyl methacrylate (HEMA) or methacrylate functional ethylene oxide macromonomers (EO) were polymerized from these “macro-initiators” to provide a hydrophilic outer layer. The use of macromolecular building blocks allows rapid attainment of high polymer in a limited number of steps with purification between transformation requiring only polymer precipitation. [less ▲]

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See detailInternal functionalization in hyperbranched polyesters
Trollsas, Michaël; Hedrick, James L.; Mecerreyes, David et al

in Journal of Polymer Science. Part A, Polymer Chemistry (1998), 35(17), 3187-3192

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See detailSynthesis of novel polymeric materials based on aliphatic polyesters by combination of different controlled polymerization methods
Jérôme, Robert ULg; Mecerreyes, David; Tian, Dong et al

in Macromolecular Symposia (1998), 132

Combination of the living ring-opening polymerization (ROP) of ε-CL and lactides with the "controlled" free radical polymerization of styrene and methacrylic monomers is a versatile strategy for the ... [more ▼]

Combination of the living ring-opening polymerization (ROP) of ε-CL and lactides with the "controlled" free radical polymerization of styrene and methacrylic monomers is a versatile strategy for the synthesis of well-defined block and graft copolymers. In this respect, the dual "living" polymerization strategy in which two different functional groups on a single molecule used to initiate the two controlled mechanisms is particularly efficient. Combination of ROP and step-growth polymerization is another versatile methodology for the preparation of a large variety of new materials, e.g. polyimide nanofbams, polyester/silica hybrid materials and star and branched polyesters by dendritic initiation. [less ▲]

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See detailSimultaneous dual living polymerizations: a novel one-step approach to block and graft copolymers
Mecerreyes, David; Moineau, Georges; Dubois, Philippe ULg et al

in Angewandte Chemie (International ed. in English) (1998), 37(9), 1274-1276

Just one step is required for the synthesis of block copolymers by simultaneous living/controlled ring-opening and radical polymerization initiated by a difunctional (A-B) compound (shown schematically on ... [more ▼]

Just one step is required for the synthesis of block copolymers by simultaneous living/controlled ring-opening and radical polymerization initiated by a difunctional (A-B) compound (shown schematically on the right). [less ▲]

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See detailHighly functional branched and dendri-graft aliphatic polyesters through ring opening polymerization
Trollsas, Michaël; Hedrick, James L.; Mecerreyes, David et al

in Macromolecules (1998), 31(9), 2756-2763

Highly branched poly(ε-caprolactones) with novel and well-defined molecular architectures have been synthesized by the use of new multifunctional initiators. The ring-opening polymerization methods used ... [more ▼]

Highly branched poly(ε-caprolactones) with novel and well-defined molecular architectures have been synthesized by the use of new multifunctional initiators. The ring-opening polymerization methods used to prepare these new structures allowed accurate control of molecular weight and narrow molecular weight distributions. In addition, the synthesis of even more complex molecular architectures was possible by the use of 1,4,9-trioxaspiro[4.6]-9-undecanone as a comonomer with ε-caprolactone. After copolymerization, complete deacetalization of the polyester chains into the corresponding ketone groups followed by quantitative reduction formed polymers with hydroxyl pendant groups. With this synthetic strategy, significant additional functionality was introduced. In addition, the pendant hydroxyl groups along the chains can serve as macroinitiators for the further initiation of ε-caprolactone to prepare dendri-graft molecular architectures. The new polymers were characterized by 1H NMR, 13C NMR, and size exclusion chromatography (SEC). 13C NMR spectra clearly showed that the hydroxyl groups of the initiators were fully substituted to give polymers with two, four, and six arms. [less ▲]

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See detailDual living free radical and ring opening polymerizations from a double-headed initiator
Hawker, Craig J; Hedrick, James L; Malmström, Eva E et al

in Macromolecules (1998), 31(2), 213-219

The concept of performing dual living polymerizations from a single initiating molecule with no intermediate activation, or transformation, steps is presented. The compatibility of “living”, or controlled ... [more ▼]

The concept of performing dual living polymerizations from a single initiating molecule with no intermediate activation, or transformation, steps is presented. The compatibility of “living”, or controlled free radical procedures, either nitroxide mediated or atom transfer radical polymerization (ATRP), with the living ring opening polymerization of ε-caprolactone, and vice versa, is demonstrated by the synthesis of a variety of well-defined block copolymers. For example, from a hydroxy-functionalized alkoxyamine, either the living ring opening polymerization of ε-caprolactone, or the “living” free radical polymerization of styrene can be performed leading to narrow polydispersity polymeric initiators. These polymeric initiators can then be used to initiate the living polymerization of the other monomer system without the need for intermediate steps. In a similar way, hydroxy-functionalized ATRP initiators can be used as bifunctional initiators for the polymerization of both ε-caprolactone and a variety of other vinyl monomers. The novel block copolymers that are obtained were shown to have low polydispersities and controllable molecular weights for both of the blocks. [less ▲]

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See detailBlock and random copolymers of ε-caprolactone
Duda, Andrzej; Biela, Tadeusz; Libiszowski, Jan et al

in Polymer Degradation & Stability (1998), 59(1-3), 215-222

Conditions of the living homopolymerization of epsilon-caprolactone (CL), lactides (LA), and of the homo-oligomerization of gamma-butyrolactone (BL) are briefly described. Then block and random ... [more ▼]

Conditions of the living homopolymerization of epsilon-caprolactone (CL), lactides (LA), and of the homo-oligomerization of gamma-butyrolactone (BL) are briefly described. Then block and random copolymerizations of CL with LA are shortly reviewed. The microstructure of the resulting copolyesters in relation to some peculiarities of these processes is discussed in more detail. It is also shown that the otherwise 'non-polymerizable' BL does form high molecular weight copolymers with CL, containing up to 50 mol% repeating units derived from BL. Their molecular weight is controlled by the concentrations of the consumed comonomers and the starting concentration of the initiator. NMR and DSC data indicate the random structure of copolymers. TGA traces of the BL/CL copolymers show that the presence of the gamma-oxybutyryl repeating units randomly distributed within the poly(CL) chains improves the thermal stability of the latter. [less ▲]

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