Nitroxide-mediated polymerization of styrene and limonene in the framework of synthesis of potentially functional polymers using naturally occurring terpenes

Andriotis, Eleftherios G.; Koumbis, Alexandros E.; Achilias, Dimitris S.

doi:10.1007/s00289-020-03333-x

Cited by 8 publications

(4 citation statements)

References 39 publications

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“…Figure 3 is a graphical representation of the polymerization reaction progress for 180 min. For P(MMA-TEGDMA) nanoparticles synthesis, a rapid conversion is observed (over 90% conversion in the first 20 min), compared to D-limonene loaded P(MMA-TEGDMA) polymerization reaction, where deceleration is observed, attributed to the known radical scavenging and chain transfer agent activity of D-limonene [ 30 , 35 , 36 ], when present in radical polymerization systems.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of D-Limonene Loaded Polymeric Nanoparticles with Enhanced Antimicrobial Properties for Potential Application in Food Packaging

et al. 2021

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Mini-emulsion polymerization was applied for the synthesis of cross-linked polymeric nanoparticles comprised of methyl methacrylate (MMA) and Triethylene Glycol Dimethacrylate (TEGDMA) copolymers, used as matrix-carriers for hosting D-limonene. D-limonene was selected as a model essential oil, well known for its pleasant odor and its enhanced antimicrobial properties. The synthesized particles were assessed for their morphology and geometric characteristics by Dynamic Light Scattering (DLS) and Scanning Electron Microscopy (SEM), which revealed the formation of particles with mean diameters at the nanoscale (D[3,2] = 0.135 μm), with a spherical shape, while the dried particles formed larger clusters of several microns (D[3,2] = 80.69 μm). The percentage of the loaded D-limonene was quantified by Thermogravimetric Analysis (TGA), complemented by Gas Chromatography-Mass Spectrometry analysis coupled with a pyrolysis unit (Py/GC-MS). The results showed that the volatiles emitted by the nanoparticles were composed mainly of D-limonene (10% w/w of dry particles). Particles subjected to higher temperatures tended to decompose. The mechanism that governs the release of D-limonene from the as-synthesized particles was studied by fitting mathematical models to the release data obtained by isothermal TGA analysis of the dry particles subjected to accelerated conditions. The analysis revealed a two-stage release of the volatiles, one governed by D-limonene release and the other governed by TEGDMA release. Finally, the antimicrobial potency of the D-limonene-loaded particles was demonstrated, indicating the successful synthesis of polymeric nanoparticles loaded with D-limonene, owing to enhanced antimicrobial properties. The overall performance of these nanoparticles renders them a promising candidate material for the formation of self-sterilized surfaces with enhanced antimicrobial activity and potential application in food packaging.

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Section: Resultsmentioning

confidence: 99%

Synthesis of D-Limonene Loaded Polymeric Nanoparticles with Enhanced Antimicrobial Properties for Potential Application in Food Packaging

et al. 2021

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“…al studied with styrene. 30 Except for a few, above-mentioned studies are mostly based on the use of volatile organic solvents and special catalysts. 21,31 However, greener polymerization processes require minimizing the use of volatile organic solvents and other toxic feedstocks in addition to reducing petroleum-based building blocks.…”

Section: Introductionmentioning

confidence: 99%

Bio‐based macroporous polymer sorbents: Synthesis, physicochemical properties and sorption kinetics

Sözbir,

Kekevi,

Mert

et al. 2024

J of Applied Polymer Sci

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Macroporous polymeric sorbents were synthesized via high internal phase emulsion (HIPE) templating. For this aim, water‐in‐oil (w/o) HIPEs were prepared with 80 vol.% of aqueous internal phase whereas plant‐based β‐myrcene (My) and D‐limonene (Lim) were used as renewable building blocks in the continuous oil phase. Moreover, biocompatible ethylene glycol dimetacrylate (EGDMA) was also added as a crosslinker comonomer. By varying the total volume fraction of My and Lim in the continuous phase composition between 90% and 50%, 14 different HIPE formulations were prepared. After polymerization of HIPE templates 28 different sorbents were obtained depending on the purification procedure (extraction & drying under vacuum or freeze drying). The effect of terpene composition in the obtained sorbents was investigated in terms of cross‐link density (υ), the molecular weight (Mc) and pore morphology. In this context, chemical structures and pore morphologies were characterized by FTIR spectroscopy and SEM analysis, respectively. The Brunauer‐Emmet‐Teller (BET) specific surface area was also measured to determine the relationship between pore morphology and surface area. Based on the characterization results, two sorbents were selected as model for sorption tests. Thereafter, solvent sorption tests were performed by immersing sorbents in either hexane, dichloromethane, deionized water, seawater, solvent/water mixture, or solvent/seawater mixture to determine maximum sorption capacities and determine reusability of the sorbents. Moreover, experimental data was fitted to pseudo‐first order and pseudo second order kinetic models, as well as Freundlich and Langmuir isotherms. In the end, it was found that varying My and Lim ratio is the key parameter of controlling pore morphology and physicochemical properties. Moreover, it was shown that resulting sorbents can be efficiently used in oil/water separation processes repeatedly for several cycles.

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“…Atom Transfer Radical Polymerization (ATRP) is among the most widespread methods for the preparation of tailored vinyl polymers. [1][2][3] ATRP is part of the reversible deactivation radical polymerization processes, along with others developed over the last three decades: reversible addition-fragmentation chain-transfer polymerization, 4,5 nitroxide mediated polymerization, 6 and organometallic mediated radical polymerization. 7 The common denominator among them is the reversible quenching of propagating radicals, which allows for quasiliving polymerizations.…”

Section: Introductionmentioning

confidence: 99%

Influences of nitrogen base excess on ARGET ATRP of styrene with ascorbic acid acetonide and traces of oxygen and water

et al. 2023

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Nitroxide-mediated polymerization of styrene and limonene in the framework of synthesis of potentially functional polymers using naturally occurring terpenes

Cited by 8 publications

References 39 publications

Synthesis of D-Limonene Loaded Polymeric Nanoparticles with Enhanced Antimicrobial Properties for Potential Application in Food Packaging

Synthesis of D-Limonene Loaded Polymeric Nanoparticles with Enhanced Antimicrobial Properties for Potential Application in Food Packaging

Bio‐based macroporous polymer sorbents: Synthesis, physicochemical properties and sorption kinetics

Influences of nitrogen base excess on ARGET ATRP of styrene with ascorbic acid acetonide and traces of oxygen and water

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