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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: 122; Prenosov: 12
.pdf Celotno besedilo (1,75 MB)

Preparation of Synthetic and Natural Porous Polymers via Multiphase Media : doctoral dissertation
Stanko Kramer, 2023, doktorska disertacija

Opis: PolyHIPEs are highly porous polymers with an interconnecting porous structure. They have found usage in the removal of pollutants, water clean-up, oil spill removal, catalysis, controlled release of active compounds, wound dressing and tissue engineering. The wide applicability of polyHIPEs is possible through their inherent porosity and chemical diversity. The aim of this dissertation was to increase the chemical diversity of polyHIPEs, develop an efficient method for the synthesis of polyHIPE beads and to use natural resources for the synthesis of polyHIPEs, subsequently, paving the pathway to more sustainable synthetic procedures. PolyHIPEs tend to have poor mechanical properties, therefore, it was crucial to investigate the influence of the internal phase volume, initation type (photo vs thermal) and monomer functionality on the mechanical and morphological properties of thiol-ene polyHIPEs. The results show that the main factors influencing the morphological and mechanical properties are the monomer structure and the internal phase volume. Besides the inherent porosity and chemical versatility typical of polyHIPEs, they can also be produced in various shapes, e.g., monoliths, membranes and beads. Therefore, the dissertation also focuses on the synthesis of polyHIPE beads. The polyHIPE beads were produced through the usage of water-in-oil-in-water (W/O/W) multiple emulsions. To enable the synthesise of open porous polyHIPE beads, thiol-ene polymerisation was combined with photopolymerisation to guarantee a rapid polymerisation prior the break-down of the multiple emulsion. Consequently, it was possible to synthesise polyHIPE beads. The first study showed that by altering the thiol to acrylate ratio in favour of the acrylate the degradation rate of the synthesised polyHIPE beads gets reduced. Additionally, it was demonstrated that the beads can be readily functionalised with allyl amine and used for the adsorption of methylene blue (12.0 mg/g in 24 hours). The next study combined polyHIPE beads with magnetic nanoparticles (MNPs) to produce magnetic polyHIPE beads which were used for the removal of Pb2+. To produce the magnetic polyHIPE beads, magnetic nanoparticles (MNPs) were added to the organic phase. The MNPs get incorporated into the polymer-network after the polymerisation, therefore, forming magnetic polyHIPE beads. The MNPs were shown to influence the morphology and the size of the beads. Additionally, the polyHIPE beads were shown to remove up to 97.0 % of Pb2+ after 24 hours from a 2.9 mg/L solution of Pb2+. In the last study related to the synthesis of polyHIPE beads, functional polyHIPE beads were produced and then functionalised to enable the binding of the enzyme invertase. These beads were then utilised for the hydrolysis of sucrose. The conversion of sucrose to glucose and fructose was 100% after 60 minutes for the polyHIPE beads, while the conversion for non-porous beads was only 6.5%. The last part of the thesis focused on more sustainable/natural approaches to polyHIPE synthesis. The first study utilised limonene as a replacement to conventional solvents (e.g., cyclohexane) in the production of O/W HIPEs and the polymerisation thereof into polyHIPEs. It was shown that limonene can be used as an efficient replacement in the production of polyHIPEs. The next study used natural resources (terpenoids) which were modified to contain polymerisable units, which were used for the synthesis of terpenoid-based polyHIPEs. The synthesised monomers were then crosslinked with 5 and 10 mol. % TMPTA to form polyHIPEs, consequently producing porous polymers. The last study in this thesis used the terpenes limonene, carvone and myrcene to produce bio-based polyHIPEs by utilising multifunctional acrylates (PETA and TMPTA) as the comonomers. This study demonstrates that it is possible to prepare polyHIPEs from commercially available terpenes, therefore, moving the field of polyHIPEs into a more sustainable direction.
Ključne besede: HIPE, PolyHIPE, Multiple Emulsions, Functional polyHIPEs, Natural Polymers, Terpenes
Objavljeno v DKUM: 08.12.2023; Ogledov: 259; Prenosov: 51
.pdf Celotno besedilo (8,08 MB)

Chemical composition of Juniperus communis L. fruits supercritical CO2 extracts: dependence on pressure and extraction time
Branislava Barjaktarović, Milan Sovilj, Željko Knez, 2005, izvirni znanstveni članek

Opis: Ground fruits of the common juniper (Juniperus communis L), with a particle size range from 0.2500.400 mm, forming a bed of around 20.00 +/- 0.05 g, were extracted with supercritical CO2 at pressures of 80,90, and 100 bars and at a temperature of 40 De. The total amount of extractable substances or global yield (mass of extract/mass of raw material) for the supercritical fluid extraction process varled from 0.65 to 4.00"10 (wt). At each Investigated pressure, supercriticaI CO2 extract fractions collected In successive time intervals over the course of the extraction were analyzed by capillary gas chromatography, using flame ionization (GO-FIO) and mass spectrometric detection (GC-MS). More than 200 constituents were detected In the extracts, and the contents of 50 compounds were reported in the work. Dependence of the percentage yields of monoterpene, sesquiterpene, oxygenated monoterpene, and oxygenated sesquiterpene hydrocarbon groups on the extraction time was investigated, and conditions that favored the yielding of each terpene groups were emphasized. At all pressures, monoterpene hydrocarbons were almost completely extracted from the berries in the first 0.6 h. It was possible to extract oxygenated monoterpenes at 100 bar in 0.5 h and at 90 bar in 1.2 h. Contrary to that, during an extraction period of 4 h at 80 bar, it was possible to extract only 75% of the maximum yielded value of oxygenated monoterpene at 100 bar. Intensive extraction of sesquiterpenes could be by no means avoided at any pressure, but at the beginning of the process (the first 0.5 h) at 80 bar, they were extracted about a and 3 times slower than at 100 and 90 bar, respectively. Oxygenated sesquiterpenes were yielded at fast, constant extraction rates at 100 and 90 bar In 1.2 and 3 h, respectively. This initial fast extraction period was consequently foIlowed by much slower extraction of oxygenated sesquiterpenes.
Ključne besede: chemical processing, high pressure technology, CO2, supercritical fluid extraction, pressure, extraction time, Juniperus communis, oxygenated terpenes, juniper berry oil, carbon dioxide
Objavljeno v DKUM: 01.06.2012; Ogledov: 2097; Prenosov: 54
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