Biodegradable photocross-linked polymers of glycerol diglycidyl ether and structurally different alcohols

Kašėtaitė, Sigita; Ostrauskaitė, Jolita; Gražulevičienė, Violeta; Bridžiuvienė, Danguolė; Budreckienė, Rūta; Rainosalo, Egidija

doi:10.1016/j.reactfunctpolym.2017.11.005

Cited by 17 publications

(10 citation statements)

References 42 publications

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“…GDE has good adhesion as well as good thermomechanical properties. This cross-linking compound is proposed for use in the synthesis of epoxy materials that can be applied in biodegradable materials [ 31 , 32 ]. The phenolic OH groups in naringenin can readily react with the epoxy groups in the GDE cross-linking agent.…”

Section: Resultsmentioning

confidence: 99%

Novel Polymeric Biomaterial Based on Naringenin

2021

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Biomaterials prepared based on raw plant materials are becoming more and more popular due to their specific properties and environmental friendliness. Naringenin is a flavonoid naturally occurring in citrus fruit with antioxidant and pharmacological activity. Polymeric materials based on flavonoids may have favorable properties in comparison to monomeric polyphenols, such as stronger antioxidant and antimicrobial properties. One of the methods of obtaining the polymeric form of flavonoids is polymerization with a cross-linking compound. This method has already been used to obtain poly(quercetin) and poly(rutin) from a flavonol group as well as poly(catechin) from the flavan-3-ol group of flavonoids. However, to date, no polymeric forms of flavanones have been prepared in a cross-linking reaction; the aim of this study was to obtain poly(naringenin) by reaction with a cross-linking compound using glycerol diglycide ether GDE. The degree of conversion of naringenin to poly(naringenin) determined by FTIR spectroscopy was 85%. In addition, the thermal, antioxidant and antimicrobial properties of poly(naringenin) were analyzed. Poly(naringenin) was characterized by greater resistance to oxidation and better thermal stability than monomeric naringenin. Moreover, polymeric naringenin also had a better ability to scavenge ABTS and DPPH free-radicals. In contrast to monomeric form, poly(naringenin) had antimicrobial activity against Candida albicans. Polymeric biomaterial based on naringenin could potentially be used as a natural stabilizer and antimicrobial additive for polymer compositions, as well as pro-ecological materials.

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Section: Resultsmentioning

confidence: 99%

Novel Polymeric Biomaterial Based on Naringenin

2021

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“…Its properties include low shrinkage, good adhesion, and good thermo-mechanical properties. GDE can be used in the formation of epoxy materials, which can further be used in biodegradable plastics [30,31].…”

Section: Resultsmentioning

confidence: 99%

Thermally Stable and Antimicrobial Active Poly(Catechin) Obtained by Reaction with a Cross-Linking Agent

2020

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(+)-Catechin is a flavonoid with valuable antioxidant and antimicrobial properties, found in significant amounts in green tea leaves. Polymeric forms of catechin have been obtained by enzymatic reaction, photopolymerization, and polycondensation in designed processes. However, so far, poly(catechin) has not been received in the cross-linking reaction. Reactions with the cross-linking compound allowed for the preparation of antibacterial and antioxidant materials based on quercetin and rutin. The aim of the research was to obtain, for the first time, poly(catechin) by reaction with glycerol diglycide ether cross-linking compound. The polymeric form of (+)-catechin was confirmed using FTIR and UV-Vis spectroscopy. In addition, thermal analysis (TG and DSC) of the polymeric catechin was performed. The antioxidant and antibacterial activity of poly (flavonoid) was also analyzed. Poly(catechin) was characterized by greater resistance to oxidation, better thermal stability and the ability to reduce transition metal ions than (+)-catechin. In addition, the polymeric catechin had an antimicrobial activity against Staphylococcus aureus stronger than the monomer, and an antifungal activity against Aspergillus niger comparable to that of (+)-catechin. The material made on the basis of (+)-catechin can potentially be used as a pro-ecological stabilizer and functional additive, e.g., for polymeric materials as well as dressing materials in medicine.

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“…During the process, the values of G’ increase faster and exceed the values of G” showing the high viscosity Newton liquid transforms into a hard elastic polymer. In this transformation, the point where G’ = G” is commonly used to define the gel point (t gel ) [46]. At this point, the loss factor tanδ, the ratio of the viscous and the elastic portion of the viscoelastic deformation behavior (G”/G’) starts to decrease.…”

Section: Resultsmentioning

confidence: 99%

Photoinitiator Free Resins Composed of Plant-Derived Monomers for the Optical µ-3D Printing of Thermosets

et al. 2019

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In this study, acrylated epoxidized soybean oil (AESO) and mixtures of AESO and vanillin dimethacrylate (VDM) or vanillin diacrylate (VDA) were investigated as photosensitive resins for optical 3D printing without any photoinitiator and solvent. The study of photocross-linking kinetics by real-time photorheometry revealed the higher rate of photocross-linking of pure AESO than that of AESO with VDM or VDA. Through the higher yield of the insoluble fraction, better thermal and mechanical properties were obtained for the pure AESO polymer. Here, for the first time, we validate that pure AESO and mixtures of AESO and VDM can be used for 3D microstructuring by employing direct laser writing lithography technique. The smallest achieved spatial features are 1 µm with a throughput in 6900 voxels per second is obtained. The plant-derived resins were laser polymerized using ultrashort pulses by multiphoton absorption and avalanche induced cross-linking without the usage of any photoinitiator. This advances the light-based additive manufacturing towards the 3D processing of pure cross-linkable renewable materials.

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Biodegradable photocross-linked polymers of glycerol diglycidyl ether and structurally different alcohols

Cited by 17 publications

References 42 publications

Novel Polymeric Biomaterial Based on Naringenin

Novel Polymeric Biomaterial Based on Naringenin

Thermally Stable and Antimicrobial Active Poly(Catechin) Obtained by Reaction with a Cross-Linking Agent

Photoinitiator Free Resins Composed of Plant-Derived Monomers for the Optical µ-3D Printing of Thermosets

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