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See detailα-chloro-ε-caprolactone, a versatile precursor for grafting of aliphatic polyesters
Riva, Raphaël ULg; Lenoir, Sandrine ULg; Lecomte, Philippe ULg et al

Poster (2009, September 17)

Macromolecular engineering is one of the most powerful tool to synthesise many polymers of various architectures and with tailored properties. This contribution aims at reporting on a novel strategy for ... [more ▼]

Macromolecular engineering is one of the most powerful tool to synthesise many polymers of various architectures and with tailored properties. This contribution aims at reporting on a novel strategy for the macromolecular engineering of poly-ε-caprolactone (PCL) which is based on the use of a dual monomer / initiator compound, α-chloro-ε-caprolactone (αClεCL). Indeed, αClεCL is not only polymerizable by ring opening initiated by metal alkoxides, but it is also an initiator for the atom transfer radical polymerization (ATRP) of vinyl monomers, so leading easily to the synthesis of macromonomers. Polystyrene macromonomer has been prepared by this method and successfully copolymerized with ε-caprolactone (εCL) with formation of the corresponding grafted PCL. αClεCL is also a precursor of copolyesters with εCL that bear pendant chlorides. These (co)polyesters have been used as macroinitiators for the ATRP of methyl methacrylate in order to synthesise the corresponding graft copolymer. On the other hand, the pendant chlorides of poly(αClεCL-co-εCL) copolyesters were easily converted into azide with formation of the corresponding azide bearing copolyester. This copolyester was then reacted with an alkyne bearing an ATRP initiator by “Click chemistry”. The conversion of chlorides into more efficient ATRP initiators led to the improvement of the initiation efficiency of the macroinitiator. [less ▲]

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See detailContribution of "click chemistry" to the synthesis of antimicrobial aliphatic copolyester
Riva, Raphaël ULg; Lussis, Perrine ULg; Lenoir, Sandrine ULg et al

in Polymer (2008), 49(8), 2023-2028

A straightforward strategy is proposed to impart antimicrobial properties to biodegradable poly(oxepan-2-one) (poly(epsilon-caprolactone) or PCL), which is based on the grafting of pendant ammonium salts ... [more ▼]

A straightforward strategy is proposed to impart antimicrobial properties to biodegradable poly(oxepan-2-one) (poly(epsilon-caprolactone) or PCL), which is based on the grafting of pendant ammonium salts by "click" chemistry. First, statistical copolymerization of 3-chlorooxepan-2-one (alpha-chloro-epsilon-caprolactone or alpha Cl epsilon CL) with oxepan-2-one (epsilon-caprolactone or epsilon CL) was initiated by 2,2-dibutyl-2-stanna-1,3-dioxepane (DSDOP). In a second step, pendant chlorides were converted into azides by reaction with sodium azide (NaN3). Finally, quaternary ammonium containing alkynes were quantitatively added to the pendant azide groups of PCL by the copper-catalyzed Huisgen's 1,3-dipolar cycloaddition, which is a typical "click" reaction. An alternative two-step strategy based on the cycloaddition of the amine containing alkyne onto the pendant azides, followed by quaternization turned out to be less efficient. The antimicrobial activity was analyzed by the "shaking flask method" in the presence of Escherichia coli [less ▲]

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See detailGrafting of poly[2-(tert-butylamino)ethyl methacrylate] onto polypropylene by reactive blending and antibacterial activity of the copolymer
Thomassin, Jean-Michel ULg; Lenoir, Sandrine ULg; Riga, Johan ULg et al

in Biomacromolecules (2007), 8(4), 1171-1177

To combine low cost, good mechanical properties, and antibacterial activity in one material, a nonquaternized polymeric biocide, i.e., poly[2-(tert-butylamino)ethyl methacrylate] (PTBAEMA), was dispersed ... [more ▼]

To combine low cost, good mechanical properties, and antibacterial activity in one material, a nonquaternized polymeric biocide, i.e., poly[2-(tert-butylamino)ethyl methacrylate] (PTBAEMA), was dispersed within a commodity plastic, i.e., polypropylene (PP). The high immiscibility of the two polymers was tackled by reactive compatibilization and thus by reaction of commercially available maleic anhydride grafted polypropylene with primary amine-end-capped PTBAEMA. This reactive polymethacrylate was synthesized by atom-transfer radical polymerization with an azide-containing initiator. The azide end group was converted into a primary amine by the Huisgen [3 + 2] cycloaddition of propargylamine. The accordingly formed PP-g-PTBAEMA copolymer was melt dispersed within neat PP and processed as fibers, whose antimicrobial properties were assessed by the viable cell counting method against Escherichia coli. The antibacterial activity was long-lasting as a result of the anchoring of the PTBAEMA chains onto PP, which prevented them from being released from the surface of the fibers. [less ▲]

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See detailPolyolefin matrixes with permanent antibacterial activity : preparation, antibacterial activity, and action mode of the active species
Lenoir, Sandrine ULg; Pagnoulle, Christophe; Galleni, Moreno ULg et al

in Biomacromolecules (2006), 7(8), 2291-2296

Poly[2-(tert-butylamino)ethyl methacrylate] (PTBAEMA) belongs to a novel class of water-insoluble biocides. Dispersion of a poly(ethylene-co-butylene)-b-poly[2-(tert-butylamino)ethyl methacrylate] diblock ... [more ▼]

Poly[2-(tert-butylamino)ethyl methacrylate] (PTBAEMA) belongs to a novel class of water-insoluble biocides. Dispersion of a poly(ethylene-co-butylene)-b-poly[2-(tert-butylamino)ethyl methacrylate] diblock copolymer (PEB-b-PTBAEMA) within low-density polyethylene (LDPE) imparts antimicrobial properties to the polyolefin as assessed by the viable cell counting method against Escherichia coli (E. coli). This diblock copolymer has been synthesized by atom transfer radical polymerization (ATRP) with a poly(ethylene-co-butylene) (PEB) oligomer end-capped by an activated bromide as a macroinitiator for the polymerization of 2-(tert-butylamino)ethyl methacrylate (TBAEMA). Morphological changes of E. coli bacteria in contact with modified LDPE have been observed by transmission and scanning electron microscopy and indicate that the diblock copolymer is bactericide rather than bacteriostatic. Finally, the action mode of the PEB-b-PTBAEMA copolymer more likely relies on the displacement of the Ca2+ and/or Mg2+ ions of the outer membrane of the bacteria, which is disorganized and finally disrupted. [less ▲]

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See detailNew antibacterial cationic surfactants prepared by Atom Transfer Radical Polymerization
Lenoir, Sandrine ULg; Pagnoulle, Christophe; Detrembleur, Christophe ULg et al

in Journal of Polymer Science. Part A, Polymer Chemistry (2006), 44(3), 1214-1224

Efficient antibacterial surfactants have been prepared by the quaternization of the amino groups of poly(ethylene-co-butylene)-b-poly[2-(dimethylamino)ethylmethacrylate] (PEB-b-PDMAEMA) diblock copolymers ... [more ▼]

Efficient antibacterial surfactants have been prepared by the quaternization of the amino groups of poly(ethylene-co-butylene)-b-poly[2-(dimethylamino)ethylmethacrylate] (PEB-b-PDMAEMA) diblock copolymers by octyl bromide. The diblock copolymers have been synthesized by ATRP of 2-(dimethylamino)ethylmethacrylate (DMAEMA) initiated by an activated bromide-end-capped poly(ethylene-co-butylene). In the presence of CuBr, 1,4,7,10,10-hexamethyl-triethylenetetramine (HMTETA), and toluene at 50 °C, the initiation is slow in comparison with propagation. This situation has been improved by the substitution of CuCl for CuBr, all the other conditions being the same. Finally, the addition of an excess of CuCl2 (deactivator) to the CuCl/HMTETA catalyst is very beneficial in making the agreement between the theoretical and experimental number-average molecular weights excellent. The antibacterial activity of PEB-b-PDMAEMA quaternized by octyl bromide has been assessed against bacteria and is comparable to the activity of a commonly used disinfectant, that is, benzalkonium chloride. [less ▲]

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See detailAntimicrobial activity of polyestyrene particles coated by photo-crooslinked block copolymers containing a biocidal polymethacrylate block
Lenoir, Sandrine ULg; Pagnoulle, Christophe; Detrembleur, Christophe ULg et al

in e-Polymers (2005), 74

A commercially available poly(ethylene-co-butylene) copolymer, end-capped by a short polyisoprene block and a hydroxyl group (PI-b-PEB-OH), has been derivatized into a macroinitiator for atom transfer ... [more ▼]

A commercially available poly(ethylene-co-butylene) copolymer, end-capped by a short polyisoprene block and a hydroxyl group (PI-b-PEB-OH), has been derivatized into a macroinitiator for atom transfer radical polymerization (ATRP) by esterification of the hydroxyl end-group by an activated bromide-containing acyl bromide. Two types of triblock copolymers, Pl-b-PEB-b-poly(dimethylaminoethyl methacrylate) (PDMAEMA) and Pl-b-PEB-b-poly[2-(tert-butylamino)ethyl methacrylate] (PTBAEMA), have been synthesized and used to coat polystyrene particles. These coatings have been permanently immobilized by UV cross-linking of the isoprene units. They exhibit a biocidal activity against Gram-negative bacteria either intrinsically in case of the PTBAEMA block or upon quaternization of the PDMAEMA block by octyl bromide. The antimicrobial activity is directly related to the concentration of coated PS particles in the medium. [less ▲]

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See detailFunctionalization of poly(epsilon-caprolactone) by pendant hydroxyl, carboxylic acid and epoxide groups by atom transfer radical addition
Riva, Raphaël ULg; Lenoir, Sandrine ULg; Jérôme, Robert ULg et al

in Polymer (2005), 46(19), 8511-8518

A straightforward strategy is proposed for grafting hydroxyl, carboxylic acid and epoxide groups along poly (epsilon-caprolactone) chains. Statistical copolymerization of epsilon-caprolactone (epsilon-CL ... [more ▼]

A straightforward strategy is proposed for grafting hydroxyl, carboxylic acid and epoxide groups along poly (epsilon-caprolactone) chains. Statistical copolymerization of epsilon-caprolactone (epsilon-CL) with alpha-chloro-epsilon-caprolactone (alpha-Cl-epsilon-CL) has been initiated by 2,2-dibutyl-2-stanna-1,3-dioxepane (DSDOP), followed by the atom transfer radical addition (ATRA) of but-3-en-1-ol, vinylacetic acid and 1,2-epoxyhex-5-ene, respectively, onto the alpha-chloro units of a poly(alpha-Cl-epsilon-CL-co-epsilon-CL) copolymer. alpha-Cl-epsilon-CL is easily prepared by the Baeyer-Villiger oxidation of 2-chlorocyclohexanone. The influence of the experimental conditions, i.e. temperature, solvent, catalyst, on the grafting yield has been discussed. Because ATRA is tolerant of the investigated functional groups, no protection/deprotection reaction is required, which is a major advantage of the method. [less ▲]

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See detailSynthesis of copolymer brushes endowed with adhesion to stainless steel surfaces and antibacterial properties by controlled nitroxide-mediated radical polymerization
Ignatova, Miléna; Voccia, Samuel; Gilbert, Bernard ULg et al

in Langmuir (2004), 20(24), 10718-10726

Novel copolymer brushes have been synthesized by a two-step "grafting from" method that consists of the electrografting of poly(2-phenyl-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethylacrylate) onto ... [more ▼]

Novel copolymer brushes have been synthesized by a two-step "grafting from" method that consists of the electrografting of poly(2-phenyl-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethylacrylate) onto stainless steel, followed by the nitroxide-mediated radical polymerization of 2-(dimethylamino ethyl)acrylate and styrene or n-butyl acrylate, initiated from the electrografted polyacrylate chains. The grafted copolymers were quaternized in order to endow them with antibacterial properties. Peeling tests have confirmed the strong adhesion of the grafted copolymer onto the stainless steel substrate. Quartz crystal microbalance experiments have proven that fibrinogen adhesion is lower on the hydrophilic quaternized films compared to the nonionic counterpart. Such quaternized copolymers exhibit significant antibacterial activity against the Gram-positive bacteria S. aureus and the Gram-negative bacteria E. coli. [less ▲]

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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 detailImmobilization of silver in polypyrrole/polyanion composite coatings: Preparation, characterization, and antibacterial activity
Ignatova, Milena; Labaye, David; Lenoir, Sandrine ULg et al

in Langmuir (2003), 19(21), 8971-8979

Thin films of polypyrrole doped by polyanions have been deposited onto stainless steel and carbon fibers by anodic electropolymerization of pyrrole in the presence of an anionic polyelectrolyte in water ... [more ▼]

Thin films of polypyrrole doped by polyanions have been deposited onto stainless steel and carbon fibers by anodic electropolymerization of pyrrole in the presence of an anionic polyelectrolyte in water. Films with a thickness smaller than 600 nm have been formed, which strongly adhere to the solid supports. The polymeric dopant has been selected for its ability to complex silver ions. Scanning electron microscopy, Rutherford backscattering analyses, and IR spectroscopy have confirmed that silver is actually immobilized in the films and provides them with an antibacterial activity against the Gram-negative bacteria Escherichia coli and Gram-positive bacteria Staphylococcus aureus. [less ▲]

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See detailSynthesis and ring-opening polymerization of α-chloro-ε-caprolactone
Lecomte, Philippe ULg; Lenoir, Sandrine ULg; Xudong, Lou et al

Poster (2001, May 16)

Detailed reference viewed: 26 (4 ULg)