Microgel Preparation by Miniemulsion Polymerization of Passerini Multicomponent Reaction Derived Acrylate Monomers

Abstract

Three acrylate monomers featuring different side-groups are synthesized in yields up to 94% in a one-pot procedure using the versatile Passerini-three-component reaction. The procedure for their miniemulsion polymerization into polymeric particles with tunable sizes is established. Ethylene glycol dimethacrylate is introduced as comonomer to induce crosslinking and enable the production of microgels. Besides the shelf life of the miniemulsions, the dependence of the particle size on the concentration of the surfactant (sodium dodecyl sulfate) and the crosslinker, as well as the sonication amplitude and time, is investigated. The particle size of the collapsed microgels range from 21 to 91 nm. The swelling of the microgels in organic solvents is studied.

Aqueous microgels with engineered hydrophobic nano-domains

“…Microgels of different size and hydrophobicity were synthesized by Windbiel et al from acrylate monomers functionalized with different side groups, using miniemulsion polymerization with water being the continuous phase (O/W). 66 The monomers were pre-synthesized following a Passerini three-component reaction employing acrylic acid (AA) and aldehydes, as well as isocyanates, of different hydrophobicity. Microgels were obtained by radical polymerization and crosslinking of the obtained monomers in miniemulsion, using EGDMA as a cross-linker.…”

Predicting the Volume Phase Transition Temperature of Multi-Responsive Poly(N-isopropylacrylamide)-Based Microgels Using a Cluster-Based Partial Least Squares Modeling Approach

“…10,12−14 Alternately, post-polymerization modification of a functionalized microgel can be used to introduce a functional group often not compatible with the precipitationbased free radical process typically used for microgel synthesis. 15,16 Coupling temperature sensitivity with pH-responsiveness in microgels can unlock applications in sensing, 17 drug delivery, 18 catalysis, 19−21 and tissue engineering or cell scaffolding. 22 The T h i s c o n t e n t i s specific pH and magnitude of the pH-induced transition can be controlled by incorporating anionic or cationic functional comonomers with different pK a values.…”

“…The incorporation of other functional comonomers into PNIPAM microgels can create a multi-responsive microgel in which the swelling/deswelling transitions can be regulated by two or more external stimuli. , The nature of the dual stimulus swelling response can be adjusted by changing the type/amount of the comonomer used, the distribution of the comonomer within the microgel, and/or other polymerization conditions. ,− Alternately, post-polymerization modification of a functionalized microgel can be used to introduce a functional group often not compatible with the precipitation-based free radical process typically used for microgel synthesis. , …”