Glycidyl Methacrylate-Based Copolymers as Healing Agents of Waterborne Polyurethanes

Tzoumani, Ioanna; Beobide, Amaia Soto; Iatridi, Zacharoula; Voyiatzis, George A.; Bokias, Georgios; Kallitsis, Joannis K.

doi:10.3390/ijms23158118

Cited by 12 publications

(10 citation statements)

References 71 publications

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“…Similarly, poly(glycidyl methacrylate) is a promising polymer having epoxy units that may be further chemically modified. Glycidyl methacrylate (GMA) is a less expensive and low-toxicity monomer that copolymerizes readily with an appropriate comonomer [ 20 ]. The reactive epoxy groups of the GMA units easily react with thiol or amine groups containing functional molecules, increasing the practical application of the resultant copolymer system.…”

Section: Introductionmentioning

confidence: 99%

pNIPAm-Based pH and Thermoresponsive Copolymer Hydrogel for Hydrophobic and Hydrophilic Drug Delivery

Mohan,

Santhamoorthy,

Phan

et al. 2024

Gels

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The regulated and targeted administration of hydrophobic and hydrophilic drugs is both promising and challenging in the field of drug delivery. Developing a hydrogel which is responsive to dual stimuli is considered a promising and exciting research area of study. In this work, melamine functionalized poly-N-isopropyl acrylamide-co-glycidyl methacrylate copolymer has been developed by copolymerizing glycidyl methacrylate (GMA) monomer with N-isopropyl acrylamide (NIPAm) and further functionalized with melamine units (pNIPAm-co-pGMA-Mela). The prepared pNIPAm-co-pGMA-Mela copolymer hydrogel was characterized using various characterization techniques, including 1H NMR, FTIR, SEM, zeta potential, and particle size analysis. A hydrophobic drug (ibuprofen, Ibu) and hydrophilic drug (5-fluorouracil, 5-Fu) were selected as model drugs. Dual pH and temperature stimuli-responsive drug release behavior of the pNIPAm-co-pGMA-Mela hydrogel was evaluated under different pH (pH 7.4 and 4.0) and temperature (25 °C, 37 °C, and 45 °C) conditions. Furthermore, the in vitro biocompatibility of the developed pNIPAm-co-pGMA-Mela copolymer hydrogel was determined on MDA-MB-231 cells. The pH and temperature-responsive drug delivery study results reveal that the pNIPAm-co-pGMA-Mela hydrogel system is responsive to both pH and temperature stimuli and exhibits about ~100% of Ibu and 5-Fu, respectively, released at pH 4.0/45 °C. Moreover, the MTT assay and hemocompatibility analysis results proved that the pNIPAm-co-pGMA-Mela hydrogel system is biocompatible and hemocompatible, suggesting that that it could be used for drug delivery applications. The experimental results suggest that the proposed pNIPAm-co-pGMA-Mela hydrogel system is responsive to dual pH and temperature stimuli, and could be a promising drug carrier system for both hydrophilic and hydrophobic drug delivery applications.

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Section: Introductionmentioning

confidence: 99%

pNIPAm-Based pH and Thermoresponsive Copolymer Hydrogel for Hydrophobic and Hydrophilic Drug Delivery

Mohan,

Santhamoorthy,

Phan

et al. 2024

Gels

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“…In our research group, we are currently focusing on the development of self-healing materials for waterborne polyurethane (WPUs) coatings [ 23 , 24 , 25 ]. One of our methodologies is based on the effective encapsulation of active compounds, which, when released, will impart additional functionalities, with the self-healing ability being a first target.…”

Section: Introductionmentioning

confidence: 99%

“…In all stages, we proceeded to a systematic comparative study of two diisocyanate compounds as encapsulated functional agents, namely the cyclic-chain isophorone diisocyanate (IPDI) and the open-chain hexamethylene diisocyanate (HDI). HDI would be a safer alternative for applications since it is characterized by a lower toxicity [ 24 ]. On the other hand, HDI is more reactive than IPDI [ 23 ], potentially leading to implications as it concerns the stability and possible long-term application of the respective microcapsules.…”

Section: Introductionmentioning

confidence: 99%

Controlling the Synthesis of Polyurea Microcapsules and the Encapsulation of Active Diisocyanate Compounds

Avdeliodi,

Tsioli,

Bokias

et al. 2024

Polymers

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The encapsulation of active components is currently used as common methodology for the insertion of additional functions like self-healing properties on a polymeric matrix. Among the different approaches, polyurea microcapsules are used in different applications. The design of polyurea microcapsules (MCs) containing active diisocyanate compounds, namely isophorone diisocyanate (IPDI) or hexamethylene diisocyanate (HDI), is explored in the present work. The polyurea shell of MCs is formed through the interfacial polymerization of oil-in-water emulsions between the highly active methylene diphenyl diisocyanate (MDI) and diethylenetriamine (DETA), while the cores of MCs contain, apart from IPDI or HDI, a liquid Novolac resin. The hydroxyl functionalities of the resin were either unprotected (Novolac resin), partially protected (Benzyl Novolac resin) or fully protected (Acetyl Novolac resin). It has been found that the formation of MCs is controlled by the MDI/DETA ratio, while the shape and size of MCs depends on the homogenization rate applied for emulsification. The encapsulated active compound, as determined through the titration of isocyanate (NCO) groups, was found to decrease with the hydroxyl functionality content of the Novolac resin used, indicating a reaction between NCO and the hydroxyl groups. Through the thorough investigation of the organic phase, the rapid reaction (within a few minutes) of MDI with the unprotected Novolac resin was revealed, while a gradual decrease in the NCO groups (within two months) has been observed through the evolution of the Attenuated Total Reflectance—Fourier-Transform Infrared (ATR-FTIR) spectroscopy and titration, due to the reaction of these groups with the hydroxyl functionalities of unprotected and partially protected Novolac resin. Over longer times (above two months), the reaction of the remaining NCO groups with humidity was evidenced, especially when the fully protected Acetyl Novolac resin was used. HDI was found to be more susceptible to reactions, as compared with IPDI.

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“…Glycidyl methacrylate (GMA) is a considerably hydrophobic and non-toxic monomer, a highly reactive, cheaper monomer, which can be easily copolymerized with reliable comonomers to produce multifunctional polymers. Due to the high reactivity of the pendant epoxy groups with amine or thiol groups, it can be utilized further to modify appropriate functional units and improve the applicability of the resulting copolymers [3,4].…”

Section: Introductionmentioning

confidence: 99%

L-Lysine-Modified pNIPAm-co-GMA Copolymer Hydrogel for pH- and Temperature-Responsive Drug Delivery and Fluorescence Imaging Applications

Moorthy

Vanaraj

Thirupathi³

et al. 2023

Gels

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The development of dual-stimuli-responsive hydrogels attracts much research interest owing to its unique stimuli-responsive characteristics. In this study, a poly-N-isopropyl acrylamide-co-glycidyl methacrylate-based copolymer was synthesized by incorporating N-isopropyl acrylamide (NIPAm) and a glycidyl methacrylate (GMA) monomer. The synthesized copolymer, pNIPAm-co-GMA was further modified with L-lysine (Lys) functional units and further conjugated with fluorescent isothiocyanate (FITC) to produce a fluorescent copolymer pNIPAAm-co-GMA-Lys hydrogel (HG). The in vitro drug loading and dual pH- and temperature-stimuli-responsive drug release behavior of the pNIPAAm-co-GMA-Lys HG was investigated at different pH (pH 7.4, 6.2, and 4.0) and temperature (25 °C, 37 °C, and 45 °C) conditions, respectively, using curcumin (Cur) as a model anticancer drug. The Cur drug-loaded pNIPAAm-co-GMA-Lys/Cur HG showed a relatively slow drug release behavior at a physiological pH (pH 7.4) and low temperature (25 °C) condition, whereas enhanced drug release was achieved at acidic pH (pH 6.2 and 4.0) and higher temperature (37 °C and 45 °C) conditions. Furthermore, the in vitro biocompatibility and intracellular fluorescence imaging were examined using the MDA-MB-231 cell line. Therefore, we demonstrate that the synthesized pNIPAAm-co-GMA-Lys HG system with temperature- and pH-stimuli-responsive features could be promising for various applications in biomedical fields, including drug delivery, gene delivery, tissue engineering, diagnosis, antibacterial/antifouling material, and implantable devices.

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Glycidyl Methacrylate-Based Copolymers as Healing Agents of Waterborne Polyurethanes

Cited by 12 publications

References 71 publications

pNIPAm-Based pH and Thermoresponsive Copolymer Hydrogel for Hydrophobic and Hydrophilic Drug Delivery

pNIPAm-Based pH and Thermoresponsive Copolymer Hydrogel for Hydrophobic and Hydrophilic Drug Delivery

Controlling the Synthesis of Polyurea Microcapsules and the Encapsulation of Active Diisocyanate Compounds

L-Lysine-Modified pNIPAm-co-GMA Copolymer Hydrogel for pH- and Temperature-Responsive Drug Delivery and Fluorescence Imaging Applications

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