Analysis of Double Bond Conversion of Photopolymerizable Monomers by FTIR-ATR Spectroscopy

Herrera‐González, Ana M.; Caldera‐Villalobos, Martín; Pérez‐Mondragón, Alma Antonia; Cuevas‐Suárez, Carlos Enrique; González-López, José Abraham

doi:10.1021/acs.jchemed.8b00659

Cited by 51 publications

(33 citation statements)

References 16 publications

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“…The conversion of naringenin to poly(naringenin) was calculated from the FTIR spectra. The peak at 1455 cm −1 , corresponding to the vibration of the aromatic ring, did not change after the cross-linking reaction with GDE and was, thus, used as an internal reference [ 36 , 37 ]. The appearance of novel aryl bonds is specific for the polymerization of naringenin as well as other poly (flavonoids) such as quercetin, rutin and catechin [ 26 , 27 , 28 ].…”

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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“…The peak between 1450 and 1500 cm −1 , corresponding to the aromatic ring vibration, was used for the calculations. The peak at 1455 cm −1 did not change after the polymerization reaction and therefore it can be used as an internal reference [33,34]. Moreover, the peak at 1360 cm −1 , typical for the aryl stretching vibrations was used to calculate the degree of conversion.…”

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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“…In contrast, the signature assigned to the aromatic C]C stretching mode stays constant during the polymerization reaction since the benzyl ring does not participate in the conversion from monomer to polymer. [50][51][52][53][54] Two representative spectra of the Bis-GMA lm are shown in Fig. 7(a) in the non-exposed (blue, monomer) and the nano-LED exposed area (red trace, corresponding to dark areas in the SEM micrograph).…”

Section: Resultsmentioning

confidence: 99%