The aza-Michael reaction as an alternative strategy to generate advanced silicon-based (macro)molecules and materials

Genest, Aymeric; Portinha, Daniel; Fleury, Étienne; Ganachaud, François

doi:10.1016/j.progpolymsci.2017.02.002

Cited by 94 publications

(81 citation statements)

References 137 publications

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“…The biobased spermine and spermidine makes it additionally environmentally friendly. 39 NCs were prepared using the miniemulsion technique, in which nanodroplets of a (macro)monomeric phase are dispersed in a continuous aqueous phase. 40 The miniemulsion was prepared prior to polymerization by high shear forces with an ultrasonic tip, which breaks down the disperse phase into nanodroplets, typically droplet size range from 50 to 500 nm, depending on the conditions applied during the preparation.…”

Section: Results and Discussionmentioning

confidence: 99%

Bio-Based Lignin Nanocarriers Loaded with Fungicides as a Versatile Platform for Drug Delivery in Plants

et al. 2020

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Lignin-based nano- and microcarriers are a promising biodegradable drug delivery platform inside of plants. Many wood-decaying fungi are capable of degrading the wood component lignin by segregated lignases. These fungi are responsible for severe financial damage in agriculture, and many of these plant diseases cannot be treated today. However, enzymatic degradation is also an attractive handle to achieve a controlled release of drugs from artificial lignin vehicles. Herein, chemically cross-linked lignin nanocarriers (NCs) were prepared by aza-Michael addition in miniemulsion, followed by solvent evaporation. The cross-linking of lignin was achieved with the bio-based amines (spermine and spermidine). Several fungicides—namely, azoxystrobin, pyraclostrobin, tebuconazole, and boscalid—were encapsulated in situ during the miniemulsion polymerization, demonstrating the versatility of the method. Lignin NCs with diameters of 200–300 nm (determined by dynamic light scattering) were obtained, with high encapsulation efficiencies (70–99%, depending on the drug solubility). Lignin NCs successfully inhibited the growth of Phaeomoniella chlamydospora and Phaeoacremonium minimum , which are lignase-producing fungi associated with the worldwide occurring fungal grapevine trunk disease Esca. In planta studies proved their efficiency for at least 4 years after a single injection into Vitis vinifera (“Portugieser”) plants on a test vineyard in Germany. The lignin NCs are of high interest as biodegradable delivery vehicles to be applied by trunk injection against the devastating fungal disease Esca but might also be promising against other fungal plant diseases.

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Section: Results and Discussionmentioning

confidence: 99%

Bio-Based Lignin Nanocarriers Loaded with Fungicides as a Versatile Platform for Drug Delivery in Plants

et al. 2020

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“…Therefore, the benefit of MAL was hypothesized to be the additional anionic stability, it brought to the particle and further aid in its molecular transport during emulsion polymerization. In addition, aza‐Michael addition between the primary amine functional PUM species and acrylic monomer cannot be ruled out as an alternative path toward mixing of the phases . Future work will examine varying end group vinyl functionality to improve copolymerization kinetics between the macromer and acrylic monomers.…”

Section: Resultsmentioning

confidence: 99%

Self‐assembled polyurea macromer nanodispersion and resulting hybrid polyurea‐acrylic emulsions and films

Drake

Cardoen

Hughes

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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A polyurea macromer (PUM) was synthesized and dispersed in basic conditions to form self‐assembled nanoparticles (<20 nm dispersions, up to 30 wt % aq. soln.). These nanoparticles enabled surfactant‐free emulsion polymerization to form hybrid polyurea‐acrylic particles despite the absence of a measureable water‐soluble fraction. The Tg of the starting PUM material was a strong function of the PUM's extent of neutralization and hydration (varying between 100 °C and >175 °C) due to changes in hydrogen and ionic bonding. Two separate hybrid polyurea‐acrylic emulsion systems were prepared: one by direct polymerization of (meth)acrylic monomers in the presence of the nanodispersion and a second by a physical blend of PUM nanodispersion with an acrylic latex control. The direct polymerization method resulted in a hybrid emulsion particle size that developed by a mechanism resembling conventional emulsion polymerization and was unlike that described for seeded polyurethane dispersion systems. Film hardness was shown to increase with increasing coating thickness for the hybrid film prepared by direct polymerization. The resulting mechanical properties could be explained by applying mechanical models for a composite foam structure. These results were unprecedented for normal elastomer films. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1373–1388

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“…The presence of amines there as curing agents in aza‐ Michael addition overcomes the intrinsic oxygen inhibition problem in photopolymerization. On the other hand, when building PDMS polymeric networks, aza‐ Michael addition reaction has seldom occurred with acrylate PDMS, merely due to its harder availability, compared with the much more frequently reported amino‐silicon‐based molecules 29,30…”

Section: Introductionmentioning

confidence: 99%

Aza‐Michael Addition Chemistry for Tuning the Phase Separation of PDMS/PEG Blend Coatings and Their Anti‐Fouling Potentials

Zhou

Yang

2020

Macro Chemistry & Physics

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Free adjustment of micro/nanophase‐separation degrees in coatings is not easily accessible, which is a big handicap in the development of phase‐separation‐related applications. Here, by utilizing the reactivity difference between two phases, a two‐step aza‐Michael addition pre‐crosslinking strategy, demonstrated by acryloxy‐terminated polydimethylsiloxane/polyethylene glycol (PEG) blend coatings, is proposed for the first time to tune microphase separation degrees, and promote compatibility of the biphasic amphiphilic polymer blends. Followed by a systematic study of the two‐step pre‐crosslinking time, surface morphologies of samples with desired phase‐separation degrees are unveiled using optical microscopy, AFM, and XPS. The wettability, and anti‐fouling properties — for example, anti‐protein and anti‐marine bacterial (Shewanella) adhesion — of these coatings are assessed. Less protein adsorption is observed on those surfaces with lower receding water contact angles. Shewanella adhesion is efficiently discouraged by the introduction of PEG segments, but the trend evolved with surface wettability and micro/nanophase structure in a complex way.

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The aza-Michael reaction as an alternative strategy to generate advanced silicon-based (macro)molecules and materials

Cited by 94 publications

References 137 publications

Bio-Based Lignin Nanocarriers Loaded with Fungicides as a Versatile Platform for Drug Delivery in Plants

Bio-Based Lignin Nanocarriers Loaded with Fungicides as a Versatile Platform for Drug Delivery in Plants

Self‐assembled polyurea macromer nanodispersion and resulting hybrid polyurea‐acrylic emulsions and films

Aza‐Michael Addition Chemistry for Tuning the Phase Separation of PDMS/PEG Blend Coatings and Their Anti‐Fouling Potentials

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