Continuous-flow synthesis of polymer nanoparticles in a microreactor via miniemulsion photopolymerization

Lobry, Emeline; Jasinski, Florent; Penconi, Marta; Chemtob, Abraham; Croutxé‐Barghorn, Céline; Oliveros, Esther; Braun, André M.; Criqui, Adrien

doi:10.1039/c4ra06814a

Cited by 35 publications

(33 citation statements)

References 21 publications

(14 reference statements)

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“…[16][17][18][19][20][21] Thiol-ene step-growth polymerization in miniemulsion is currently being investigated and only a handful of articles have been published in the literature. [14][15][16][22][23][24] Furthermore, works portraying the polymerization of renewable monomers through thiol-ene polymerization in aqueous dispersed medium are still uncommon. [16] In this work, we present the synthesis and characterization of poly(thioether-ester) nanoparticles via thiol-ene polymerization in miniemulsion using a fully renewable α,ω-diene monomer obtained from 10-undecenoic acid and 1,3-propanediol, both derived from castor oil.…”

Section: Introductionmentioning

confidence: 99%

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Cardoso

Machado²,

Feuser³

et al. 2017

Euro J Lipid Sci & Tech

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Biocompatible polymeric nanoparticles are obtained via thiol-ene polymerization of a biobased monomer in miniemulsion. The α,ω-diene-diester monomer is synthesized through esterification reaction of a glycerol derivative, namely 1,3-propanediol, with 10-undecenoic acid, a long-chain diene carboxylic acid. In order to investigate how different monomeric structures behave toward thiolene polymerization in miniemulsion, two types of thiols are investigated: 1,4-butanedithiol and 2-mercaptoethyl ether. Poly(thioether-ester)s with weight average molecular weight up to 15 kDa (M n ) are obtained, depending on initiator concentration and types of surfactant and dithiol employed. Finally, biobased poly(thioether-ester) nanoparticles are submitted to cytotoxicity and hemolysis analyses. High cell viability and no significant changes in cell morphology are observed after the incubation on murine fibroblast (L929) and human cervical cancer cells (HeLa). Last, hemolysis assays revealed blood compatibility and therefore polymeric nanoparticles have been shown to be a potential alternative drug delivery vector for intravenous administration. Practical Applications: There is a great demand for polymeric systems that fulfill a number of requirements, such as biodegradability and biocompatibility, for biomedical applications. In this context, biobased polymers obtained from vegetable oils are a very attractive sustainable alternative to fossil-derived polymeric materials, presenting potential biodegradability and low toxicity. By thiol-ene reactions, polymeric materials containing ester groups in the main chain -which can undergo hydrolysis-can be prepared in miniemulsion, enabling their degradation in physiological environment and, therefore, being interesting for biomedical applications and material disposal. Such novel materials could be used in temporary implants, tissue engineering, and drug delivery systems.

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Section: Introductionmentioning

confidence: 99%

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Cardoso

Machado²,

Feuser³

et al. 2017

Euro J Lipid Sci & Tech

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“…Furthermore, in a dispersed medium, the combined effect of scattering and absorption limiting light penetration may be mitigated by an effi cient mixing within shallow channels. In an industrial context requiring productivity and minimal plugging issues, [ 11 ] a macrofl uidic reactor with millimetric channels seems more suitable than a microreactor with i.d. < 500 μm.…”

Section: Introductionmentioning

confidence: 99%

“…[ 3,4 ] Although continuous emulsion polymerizations in micro- [ 5,6 ] and macroreactors [ 7,8 ] (in particular tubular reactors [ 9,10 ] ) have always attracted signifi cant attention, some recent results have emphasized the advantage of using photochemical processes and corresponding photo reactors. [11][12][13][14] Chemists have realized that improvements involve not only the distribution control of MW and particle size, [ 15,16 ] but also high MW values, [ 13 ] polymerization rates, [ 14 ] fi lm properties, [ 17 ] energy efficiency, installation costs, and size. Aiming at a rational approach for a smarter way of conducting linear radical chain photopolymerization, we chose a simple and highly effi cient reaction set-up.…”

Section: Introductionmentioning

confidence: 99%

Flash Latex Production in a Continuous Helical Photoreactor: Releasing the Brake Pedal on Acrylate Chain Radical Polymerization

Chemtob

Lobry

Rannée

et al. 2016

Macromol. React. Eng.

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At the forefront is the radical chain polymerization, that represents 40% of all processes for the production of commercial polymers, including some of the most common plastics such as polystyrene, acrylic or vinyl polymers. It is of high interest that the propagation step governing the chain-growth may be very fast, given that the propagation rate coeffi cient ( k p ) is for most monomers in the range of 10 2 -10 4 L mol −1 s −1 . Nevertheless, the paradoxical observation is that polymer chemists have always strived to limit reactivity. The highly exothermic nature of radical chain polymerizations, the high activation energies involved, and the tendency toward the gel effect combine to make heat dissipation and polymer architecture control very challenging on an industrial scale. To avoid uncontrolled acceleration of the polymerization rate that may cause disastrous "runaway" reactions, the conventional approach consists in limiting the concentration of free monomer within the reactor through semicontinuous operations, with obvious adverse consequences for productivity. [ 2 ] With this limitation in mind, we have developed a novel eco-effi cient, "fl ash," radical chain linear photopolymerization, [ 1 ] able to reduce reaction time scales from hours to seconds. Our synergetic approach integrates macrofl ow photochemistry and emulsion-type polymerization . The result is a practical "single pass" helix photochemical reactor for the continuous photopolymerization of The continuous photopolymerization of acrylate and methacrylate monomer miniemulsions (25% solids content) is investigated at room temperature in a compact helix minireactor. Using n-butyl acrylate, the process yields 95% conversion after only 27 s residence time, and gel-free high-molecular-weight products. Under optimized conditions, a 25-fold increase in effi ciency is obtained when compared to a batch photopolymerization. The reaction set-up offers a frugal process because of moderate irradiance (2.6 mW cm −2 ), photoinitiator concentration (0.75 wt%), and low-power UV-A fl uorescent lamp.

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“…Microfluidic chips have been widely used in chemical reactions (Lim et al 2014;Lobry et al 2014;Zhang et al 2014;Zheng et al 2004) and biodetection Hoshino et al 2011;Stott et al 2010;Wang et al 2011). Laminar fluid flow in microchannels is caused by a low Reynolds number (Beebe et al 2002).…”

Section: Introductionmentioning

confidence: 99%

One-step electroplating 3D template with gradient height to enhance micromixing in microfluidic chips

Xiao

Zhang

et al. 2015

Microfluid Nanofluid

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Continuous-flow synthesis of polymer nanoparticles in a microreactor via miniemulsion photopolymerization

Abstract: Water-based photopolymerization in microreactor using compact UV fluorescent lamps can create a breakthrough technology to produce polymer latexes in a safer, more environmental-friendly and energy-efficient way.

Cited by 35 publications

References 21 publications

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Flash Latex Production in a Continuous Helical Photoreactor: Releasing the Brake Pedal on Acrylate Chain Radical Polymerization

One-step electroplating 3D template with gradient height to enhance micromixing in microfluidic chips

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