Photocross-linking of glycerol diglycidyl ether with reactive diluents

Kašėtaitė, Sigita; Ostrauskaitė, Jolita; Gražulevičienė, Violeta; Švedienė, Jurgita; Bridžiuvienė, Danguolė

doi:10.1007/s00289-015-1461-x

Cited by 12 publications

(9 citation statements)

References 25 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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“…Glycerol diglycidyl ether is derived from glycerol which is a renewable raw material that can be produced from fats and oils [32] . Currently, glycerol and its derivatives are used for various applications such in pharmaceuticals, cosmetics, as sweetener in cakes and candies, or can be chemically modified and used as monomer in the polymer synthesis [33–38] …”

Section: Introductionmentioning

confidence: 99%

“…[32] Currently, glycerol and its derivatives are used for various applications such in pharmaceuticals, cosmetics, as sweetener in cakes and candies, or can be chemically modified and used as monomer in the polymer synthesis. [33][34][35][36][37][38] These results are promising, and in order to be used as sustainable alternatives, the exact composition and structure of humins must be determined. [8] From an industrial point of view, it is important to find a tool that is able to classify humins samples according to their origin in order to predict their behavior towards an application.…”

Section: Introductionmentioning

confidence: 99%

Physico‐Chemical Properties and Principal Component Analysis of Biobased Thermosets Developed with Different Batches of Industrial Humins

Dinu¹,

Gaysinski²,

Jong

et al. 2022

ChemPlusChem

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Humins have already shown their potential as thermosetting resins to produce crosslinked networks and composites, with a large variety of properties depending on the used macromolecular approach. Our group has shown that a very interesting class of materials with tunable flexibility can be made by humins co‐polymerization with glycerol diglycidyl ether (GDE). To create a clearer picture on structure‐reactivity‐properties‐application interdependent relationship, a principal component analysis (PCA) was applied on several humins batches. The PCA allowed to obtain a clear discrimination between the humins/GDE resins samples in 3 groups which correlate very well with the results of copolymerization reactivity (DSC) and thermosets properties: crosslink density, thermal stability, tan δ, Shore D hardness values, etc.

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Photocross-linking of glycerol diglycidyl ether with reactive diluents

Cited by 12 publications

References 25 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

Physico‐Chemical Properties and Principal Component Analysis of Biobased Thermosets Developed with Different Batches of Industrial Humins

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