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Poly(HIPEs) from terpenoid-derived acrylates
Stanko Kramer, Nastja Slavič, Peter Krajnc, 2023, izvirni znanstveni članek

Opis: The need for utilization of non-fossil fuel derived sources for polymer production is growing. In this study the terpenoids tetrahydrogeraniol, citronellol and nopol were modified with an esterification procedure using acryloyl chloride, forming terpenoid acrylates. The synthesised acrylates were used for the production of hierarchically porous polymers via high internal phase emulsion (HIPE) templating with emulsions consisting of an organic (monomer) phase and an aqueous phase with a volume fraction of 85%. The acrylate terpenoids in the organic phase were crosslinked with trimethylolpropane triacrylate (TMPTA) to form the polyHIPEs. A crosslinking degree of 5 and 10 mol% was used to investigate the feasibility of polyHIPE production. While both crosslinking degrees enabled the synthesis of polymers, only the 10 mol% crosslinking yielded the typical interconnected porous cellular topology. The average primary pore diameter in the case of the tetrahydrogeraniol acrylate and citronellyl acrylate was 15.6 and 16.5 μm, respectively, while the average primary pore diameter in the case of nopol acrylate was 5.6 μm.
Ključne besede: terpenes, polyHIPE, terpenoids, bio-sourced monomers, porous polymers, high internal phase emulsions
Objavljeno v DKUM: 26.01.2024; Ogledov: 123; Prenosov: 12
.pdf Celotno besedilo (1,75 MB)

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, izvirni znanstveni članek

Opis: 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.
Ključne besede: organic chemistry, macroporous polymers, monolithic polymer supports, emulsion polymerisation, foams, functionalization of polymers, high-internal-phase emulsions
Objavljeno v DKUM: 01.06.2012; Ogledov: 2156; Prenosov: 95
URL Povezava na celotno besedilo

4-vinylbenzyl chloride based porous spherical polymer supports derived from water-in-oil-in-water emulsion
Dejan Štefanec, Peter Krajnc, 2005, izvirni znanstveni članek

Opis: 4-Vinylbenzyl chloride (VBC) based water-in-oil-in-water emulsions with 85% pore volume and 70% VBC in organic phase were prepared and polymerised by free radical polymerisation. Porous spherical particles of diameters between 50 and 150 m were obtained and their morphological structure and reactivity studied by FTIR spectroscopy, elemental analysis, optical microscopy, scanning electron microscopy and mercury intrusion porosimetry. Strong influence of the suspension stabiliser, namely poly(N-vinylpyrrolidone) (PVP), on the particle form was found. Diameters of spherical polymers particles depend on the PVP concentration, being larger with the lower concentration of PVP. Reactivity of novel supports was demonstrated by the reactions with piperidine, piperazine, tris(hydroxymethyl)methylamine and tris(2-aminoethyl)amine, all yielding corresponding amine derivatives.
Ključne besede: multiple emulsions, polymer supports, 4-vinylbenzyl chloride, solid phase synthesis, solid phase synthesis, high internal phase emulsions
Objavljeno v DKUM: 01.06.2012; Ogledov: 2020; Prenosov: 36
URL Povezava na celotno besedilo

Aryl acrylate porous functional polymer supports from water-in-oil-in-water multiple emulsions
Dejan Štefanec, Peter Krajnc, 2007, izvirni znanstveni članek

Opis: Porous functional polymer supports are a class of material of wide interest due to the possibility of immobilising reactive species. A simplified procedure was applied for the preparation of porous polymer supports using a water-in-oil-in-water multiple emulsion. The primary emulsion was a high internal phase emulsion, having a volume fraction of water phase up to 95%. Two reactive acrylates, namely 4-nitrophenyl acrylate and 2,4,6-trichlorophenyl acrylate, were (separately) incorporated in the oil phase in order to obtain porous reactive polymer supports. Both acrylates were crosslinked with either divinylbenzene or ethylene glycol dimethacrylate, and beads of size ca 60 m were obtained after the polymerisation of droplets suspended into the secondary aqueous phase. In the case of 4-nitrophenyl acrylate and divinylbenzene as a crosslinker, particles with a star shape, the core being ca 60 m in diameter and the arms ca 180 m in length, were obtained. The polymers were functionalised with morpholine, tris(2-aminoethyl)amine, piperidine or piperazine yielding supports with loadings of reactive groups of between 2.6 and 6.6 mmol g-1. The results show that multiple emulsions can be precursors for porous polymer preparation.
Ključne besede: multiple emulzije, polimerni nosilci, HIPE, organska sinteza na trdni fazi, polimerni lovilci, emulzija z visokim deležem notranje faze, aril akrilati, multiple emulsions, polymer supports, HIPE, solid phase organic synthesis, polymer supported scavengers, high internal phase emulsions, arylacrylates
Objavljeno v DKUM: 31.05.2012; Ogledov: 2704; Prenosov: 112
URL Povezava na celotno besedilo

Sebastijan Kovačič, 2011, doktorska disertacija

Opis: A new class of polyHIPE materials has been prepared using high internal phase emulsions (HIPEs) with monomers in both phases. Resulting materials, namely hybrid polyHIPE materials, are obtained consisting of hydrophobic matrix (consisted of styrene cross-linked with DVB or dicyclopentadiene) filled with hydrophilic polymer gel (polyacrylic acid or polyNIPAM) and exhibit morphology changes according to pH and temperature of the surrounding medium. Our focus with regards to the production of hybrid polyHIPE materials was the responsiveness of such materials used for flow control. This property is beneficial for controlling the flow of the solution through the monolithic polymers. Furthermore, polyHIPE materials have also been prepared by using ring opening metathesis polymerisation of monomers, such as dicyclopentadiene and norbornene. Obtained materials have Young’s moduli in the range of hundred times higher than standard polyHIPE materials with the same level of porosity which represents a very important improvement in the development of highly porous cellular polymeric materials.
Ključne besede: emulsions, high internal phase emulsions, polymers, polyHIPEs, hybrid, hybrid polyHIPE materials, ROMP, flow-through, styrene, DVB, acrylic acid, NIPAM
Objavljeno v DKUM: 04.05.2011; Ogledov: 3309; Prenosov: 310
.pdf Celotno besedilo (3,71 MB)

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