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1.
Atrazine removal by covalent bonding to piperazine functionalized PolyHIPEs
Irena Pulko, Mitja Kolar, Peter Krajnc, 2007, original scientific article

Abstract: The removal of atrazine from water by a solid phase extraction technique usinginsoluble polymers is described. Porous crosslinked polymers bearing piperazine moieties were prepared in a one step reaction from the precursor 4-nitrophenylacrylate incorporating polymers (PolyHIPE type prepared by the polymerization of the continuous phase of a high internal phase emulsion and polymer beads prepared by suspension polymerization). Polymers were applied tosequester atrazine from aqueous solutions with a concentration of 33 ppb andirreversible covalent bonding to the polymers was achieved. GC/MS/MS was used to monitor the dynamics of atrazine uptake and it was found that almost complete removal of atrazine was acomplished with an excess of polymer after 48 hours at room temperature. For comparison, polymer beads of identical chemistry but lower porosity were also used and showed significantly slower action (near complete removal after 72 hours).
Keywords: polymer supports, polymer scavengers, monoliths, emulsion polymerisation, solid-phase synthesis
Published: 31.05.2012; Views: 1393; Downloads: 67
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2.
PolyHIPE supports in batch and flow-through Suzuki cross-coupling reactions
Jane F. Brown, Peter Krajnc, Neil R. Cameron, 2005, original scientific article

Abstract: As part of ongoing research efforts to discover alternative support materials to polymer beads for use in polymer-supported synthesis, particularly under flow-through conditions, this work involves the synthesis of PolyHIPE (High Internal Phase Emulsion) polymer monoliths. PolyHIPEs containing high loadings of chloromethyl groups were efficiently prepared by the direct copolymerization of 4-vinylbenzyl chloride and divinylbenzene monomers. The 'Merrifield' PolyHIPE proved to be an excellent support for batch and flow-through Suzuki cross-coupling reactions. A remarkably high yield of pure biaryl product was obtained using the PolyHIPE support in cubic form and utilizing an electron-rich boronic acid. In comparison to polymer beads, this material was found to be a much more efficient support in both batch and continuous flow modes. PolyHIPE converted a greater amount of chloromethyl groups into biaryl product under identical reaction conditions. It is suggested that the absence of channelling with PolyHIPE monoliths gives better performance under flow-through conditions than permanently porous beads.
Keywords: polymer supports, polymer monoliths, emulsion polymerisation, solid-phase synthesis, cross-coupling reactions
Published: 01.06.2012; Views: 1311; Downloads: 41
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3.
Oil-in-water high internal phase emulsions for porous monolithic polymers
Peter Krajnc, Dejan Štefanec, 2005, published scientific conference contribution abstract

Abstract: Porous monolithic polymers are objects of many studies recently due to their wide applicability. Especially in separation methods use of monoliths is growing. Usually, porous monoliths are prepared by bulk polymerisation with the use of porogenic solvents. An alternative way of preparation is to polymerise the continuous phase of an emulsion. When the volume fraction of the internal phase exceeds 74%, the emulsion is called a HIPE (high internal phase emulsion), and a polymer derived from it, a PolyHIPE. PolyHIPEs of styrene, vinylbenzyl chloride and acrylate chemistry have been prepared from awater in oil emulsion system, where monomers are dissolved in the organic phase. We describe the reversed procedure, an oil in water high internal phaseemulsion, where monomers are water soluble. Porous polymers based on acrylic acid and crosslinked with methylenebisacrylamide were prepared by using a high internal phase emulsion with toluene as the oil phase. The influence of initiator and surfactant on the morphology was studied.
Keywords: organic chemistry, porous monolith polymers, polymer supports, preparation, emulsion polymerization, HIPE
Published: 01.06.2012; Views: 2198; Downloads: 59
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4.
Aryl acrylate based high-internal-phase emulsions as precursors for reactive monolithic polymer supports
Peter Krajnc, Dejan Štefanec, Jane F. Brown, Neil R. Cameron, 2005, original scientific article

Abstract: Water-in-oil high-internal-phase emulsions (HIPEs), containing 4-nitrophenyl acrylate and 2,4,6-trichlorophenyl acrylate as reactive monomers, were prepared and polymerized, and highly porous monolithic materials resulted. The novel materials were studied by combustion analysis, Fourier transform infrared spectroscopy scanning electron microscopy, mercury porosimetry, and N2 adsorption/desorption analysis. With both esters, cellular macroporous monolithic polymers were obtained: the use of 4-nitrophenyl acrylate resulted in a cellular material with void diameters between 3 and 7 m and approximately3-m interconnects, whereas the use of 2,4,6-trichlorophenyl acrylate yielded a foam with void diameters between 2 and 5 m, most interconnects being around 1 m. The resulting monoliths proved to be very reactive toward nucleophiles, and possibilities of functionalizing the novel polymer supports were demonstrated via reactions with amines bearing additional functional groups and via the synthesis of an acid chloride derivative. Tris(hydroxymethyl)aminomethane and tris(2-aminoethyl)amine derivatives were obtained. The hydrolysis of 4-nitrophenylacrylate removed thenitrophenyl group, yielding a monolithic acrylic acid polymer. Furthermore,functionalization to immobilized acid chloride was performed very efficiently, with more than 95% of the acid groups reacting. The measurement of the nitrogen content in 4-nitrophenyl acrylate poly(HIPE)s after various times of hydrolysis showed the influence of the total pore volume of the monolithic polymers on the velocity of the reaction, which was faster with themore porous polymer.
Keywords: organic chemistry, macroporous polymers, monolithic polymer supports, emulsion polymerisation, foams, functionalization of polymers, high-internal-phase emulsions
Published: 01.06.2012; Views: 1235; Downloads: 63
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5.
Preparation and characterization of poly(high internal phase emulsion) methacrylate monoliths and their application as separation media
Peter Krajnc, Nermina Leber, Dejan Štefanec, Sandra Kontrec, Aleš Podgornik, 2005, original scientific article

Abstract: Poly(glycidyl methacrylate-co-ethyleneglycol dimethacrylate) monolithic supports were prepared by radical polymerisation of the continuous phase of water in oil high internal phase emulsions. Morphology of monolithic materialswas studied by scanning electron microscopy and mercury intrusion porosimetry. The ratio of phase volume and the degree of crosslinking influenced the void size and pore size distribution of resulting polymers. Void sizes between 1 and 10 m were observed and average pore sizes around 100nm. Polymers with 60, 75, 80 and 90% pore volume were prepared and even samples with highest pore volume showed good mechanical stability. They were modified to bear weak-anion exchange groups and tested on the separation of standard protein mixture containing myoglobin, conalbumine and trypsin inhibitor. Good separation was obtained in a very short time similar to the separation obtained by commercial methacrylate monoliths. However, higher dispersion was observed. Bovine serum albumin dynamic binding capacity for monolith with 90% porosity was close to 9 mg/ml.
Keywords: organic chemistry, methacrylate monoliths, preparation, emulsion polymerization, high porosity, high mechanical stability, polymer chromatographic supports, monolithic methacrylate supports, protein separation
Published: 01.06.2012; Views: 1372; Downloads: 27
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6.
Ring opening metathesis polymerisation (ROMP) as a tool for polyhipes with extraordinary mechanical properties
Sebastijan Kovačič, 2013, professional article

Abstract: PolyHIPE materials have been prepared by Ring Opening Metathesis Polymerisation (ROMP) of dicyclopentadiene. Two characteristic features for successful stabilization of high internal phase emulsions (HIPEs) were tuned in order to achieve improvements regarding mechanical properties of polyHIPEs.Mechanical properties of the new materials were related to variations of the surfactant concentration and the volume ratio of the internal phase in HIPEs. Values for Youngʼs moduli were about a hundred times higher than in standard polyHIPE materials with the same level of porosity, which represents a major improvement for highly porous cellular polymeric materials. Moreover, fully interconnected macroporous morphology was found forpolyHIPEs, where respective HIPEs were stabilized with only 0.25 v% of surfactant.
Keywords: emulsion templating, ring opening metathesis polymerization, dicyclopentadiene, ROMP, mechanical characteristics, polyHIPEs
Published: 21.12.2015; Views: 676; Downloads: 35
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7.
Tailoring the mechanical and thermal properties of dicyclopentadiene polyHIPEs with the use of a comonomer
E. H. Mert, Christian Slugovc, Peter Krajnc, 2015, original scientific article

Abstract: The effect of adding a comonomer to dicyclopentadiene in high internal phase emulsions (HIPEs) on the properties of ring-opening metathesis polymerisation (ROMP) derived polyHIPEs has been investigated. With this aim, dicylopentadiene was copolymerised with norbornene in surfactant stabilized high internal phase emulsions. Morphological, mechanical and thermal properties of the resulting materials were investigated with regard to the monomer ratio. The interconnected pore structure was observed for the resulting poly(dicylopentadiene-co-norbornene) polyHIPEs. Furthermore, the new polyHIPE copolymers were found to have an improved thermal stability compared to the poly(dicylopentadiene) homopolymer.
Keywords: mechanical properties, emulsion templating, polyHIPE, dicyclopentadiene, norbornene
Published: 07.08.2017; Views: 401; Downloads: 213
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8.
Cross-linked porous poly(acrylic acid-co-acrylamide) from high internal phase emulsions: preparation and functionalisation
Janja Majer, Peter Krajnc, 2009, original scientific article

Abstract: By using emulsions with high volume fractions of internal phase as polymerisation media porous copolymers of acrylic acid and acrylamide, cross-linked by methylenebisacrylamide, were prepared. The ratio of acrylic acid to acrylamide were varied (molar ratios 70:30, 50:50, 30:70) in order to yield polymers with various loading of acidic functional groups. Porous polymers with an open-cellular architecture were obtained with void diameters between 2.8 μm and 3.9 μm and with interconnecting pores approx. 0.3 μm in diameter. The chemical composition of the polymers influenced the conversion degrees during the process of functionalisation of acidic groups to acid chloride, being the highest in the case of polymer with the lowest content of acrilyc acid.
Keywords: porous monoliths, copolymers, polyacrylic acid, polyacrylamide, plyHIPE, high internal phase emulsion
Published: 17.08.2017; Views: 659; Downloads: 67
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