Email this article 
Hydrophilic molecularly imprinted phenol-amine-formaldehyde resins
Abstract
Hydrophilic molecularly imprinted resins (MIR), which are produced using hydrophilic monomers such as phenols, aldehydes, melamine or urea, have recently attracted increasing attention for use in separation and preconcentration. Among their obvious advantages are good sorption capacity, high recovery and selectivity, as well as their reusability in aqueous solutions. In this work we applied the bulk molecular imprinting method to produce quercetin-imprinted phenol-amino-formaldehyde resin. For this purpose, phloroglucinol and melamine solutions were mixed with formaldehyde and then polyethylene glycol and quercetin (Qu) were added to the obtained solution as a porogen and a template, respectively. The mixture was stirred under heating, then left in the thermostat for a continuous time. The optimum ratio of phloroglucinol to melamine was 3:1. The average molecular mass of porogen (Mw) varied between 4000–10000 Da. The obtained MIR were eluted with ethanol-water mixture (4:1, v/v) in the Soxhlet extractor for 36 h to remove the template. The MIR were characterized by FTIR-spectroscopy, laser diffraction spectroscopy and differential thermal analysis. The maximum recovery and sorption capacity of MIR synthesized in the presence of a porogen with Mw 10000 were 47% and 4.7 μmol Qu/g, respectively. The maximum imprinting factor was 1.41. The sorption kinetics of quercetin by a non-imprinted resin (NIR) is best described by a pseudo-second-order model, while MIR has a mixed pseudo-first-second-order mechanism.
Keywords
Full Text:
PDFReferences
Lu Y, Li P, Yang C, Han Y, Yan H. One pot green synthesis of maminophenol–urea–glyoxal resin as pipette tip solid-phase extraction adsorbent for simultaneous determination of four plant hormones in watermelon juice. J Chromatogr A. 2020;1623:461214. doi:10.1016/j.chroma.2020.461214
Sungur S, Köroğlu M, Hilmi-Turgut F. Determination of per-fluorooctanoic acid (PFOA) and perfluorooctane sulfonic acid (PFOS) in food and beverages. Int J Environ Anal Chem. 2018;98:360–368. doi:10.1080/03067319.2018.1468440
He X, He Y, Huang S, Fang Z, Liu J, Ma M, Chen B. Fluoro-functionalized paper-based solid-phase extraction for analysis of perfluorinated compounds by high-performance liquid chromatography coupled with electrospray ionization–tandem mass spectrometry. J Chromatogr A. 2019;1601:79–85. doi:10.1016/j.chroma.2019.06.019
Surma M, Wiczkowski W, Cieslik E, Zieliński H. Method devel-opment for the determination of PFOA and PFOS in honey based on the dispersive Solid Phase Extraction (d-SPE) with micro-UHPLC–MS/MS system. Microchem J. 2015;121:150–156. doi:10.1016/j.microc.2015.02.008
Sznajder-Katarzyńska K, Surma M, Wiczkowski W, et al. De-termination of perfluoroalkyl substances (PFASs) in fats and oils by QuEChERS/micro-HPLC-MS/MS. Food Res Int. 2020;137:109583. doi:10.1016/j.foodres.2020.109583
Sznajder-Katarzyńska K, Surma M, Wiczkowski W, Piskuła M. A simple and benign protocol for the synthesis of deep eutectic solvents-based hydrophilic molecularly imprinted resin in wa-ter for excellent selective molecular recognition in aqueous phase. Green Chem. 2021;23:5179–5188. doi:10.1016/j.foodres.2020.109583
Wang S, Li P, Han Y, Liu H, Yan H. Selective enrichment and determination of polychlorinated biphenyls in milk by solid-phase microextraction using molecularly imprinted phenolic resin fiber coating. Anal Chim Acta. 2022;1227:340328. doi:10.1016/j.aca.2022.340328
Tang W, Row K. Fabrication of water-compatible molecularly imprinted resin in a hydrophilic deep eutectic solvent for the determination and purification of quinolones in wastewaters. Chem Eng. 2019;11:871. doi:10.3390/polym11050871
Wu Z, Zhang B, Zhou X, Li L, Yu L, Liao J, Du G. Influence of single/collective use of curing agents on the curing behavior and bond strength of soy protein-melamine-urea-formaldehyde (SMUF) resin for plywood assembly. Polymers. 2019;11:1995. doi:10.3390/polym11121995
Li P, Lu Y, Cao J, Li M, Yang C, Yan H. Imidazolium ionic-liquidmodified phenolic resin for solid-phase extraction of thidiazuron and forchlorfenuron from cucumbers. J Chroma-togr A. 2020;1623:461192. doi:10.1016/j.chroma.2020.461192
Lv T, Yan H, Cao J, Liang S. Hydrophilic molecularly imprinted resorcinol-formaldehyde-melamine resin prepared in water with excellent molecular recognition in aqueous matrices. Anal Chem. 2015;87:11084–11091. doi:10.1021/acs.analchem.5b03253
Zou D, Li P, Yang C, Han D, Yan H. Rapid determination of perfluorinated compounds in pork samples using a molecular-ly imprinted phenolic resin adsorbent in dispersive solid phase extraction-liquid chromatography tandem mass spec-trometry. Anal Chim Acta. 2022;1226:340271. doi:10.1016/j.aca.2022.340271
Han Y, Wang Z, Jia J, Bai L, Liu H, Shen S, Yan H. Newly de-signed molecularly imprinted 3-aminophenol-glyoxal-urea res-in as hydrophilic solid-phase extraction sorbent for specific simultaneous determination of three plant growth regulators in green bell peppers. Food Chem. 2020;311:125999. doi:10.1016/j.foodchem.2019.125999
Arabi M, Ostovan A, Li J, Wang X, Zhang Z, Choo J, Chen L. Molecular imprinting: green perspectives and strategies. Adv Mater. 2021;33:2100543. doi:10.1002/adma.202100543
Song Y, Ma R, Jiao C, Hao L, Wang C, Wu Q, Wang Z. Magnetic mesoporous polymelamine-formaldehyde resin as an adsor-bent for endocrine disrupting chemicals. Microchim Acta. 2018;185:19. doi:10.1007/s00604-017-2593-5
Liu M, Tran TM, Elhaj AAA, Torsetnes SB, Jensen ON, Seller-gren B, Irgum K. Molecularly imprinted porous monolithic ma-terials from melamine-formaldehyde for selective trapping of phosphopeptides. Anal Chem. 2017;89:9491–9501. doi:10.1021/acs.analchem.7b02470
Zhou T, Ding L, Che G, Jiang W, Sang L. Recent advances and trends of molecularly imprinted polymers for specific recogni-tion in aqueous matrix: Preparation and application in sample pretreatment. TrAC Trends Anal Chem. 2019;114:11-28. doi:10.1016/j.trac.2019.02.028
Zhou T, Che G, Ding L, Sun D, Li Yu. Recent progress of selec-tive adsorbents: From preparation to complex sample pre-treatment. TrAC Trends Anal Chem. 2019;121:115678. doi:10.1016/j.trac.2019.115678
Dai Y, Wu N, Liu L, Yu F, Wu Y, Jian N. Simple and efficient solid phase extraction based on molecularly imprinted resor-cinol–formaldehyde resin nanofibers for determination of trace sulfonamides in animal-origin foods. Food Chem. 2023;404:134671. doi:10.1016/j.foodchem.2022.134671
Ren J, Lu Y, Han Y, Qiao F, Yan H. Novel molecularly imprint-ed phenolic resin–dispersive filter extraction for rapid deter-mination of perfluorooctanoic acid and perfluorooctane sul-fonate in milk. Food Chem. 2023;400:134062. doi:10.1016/j.foodchem.2022.134062
Zhou T, Wang Y, Li T, Li H, Yang C, Sun D, Wang D, Liu C, Che G. Fabricating magnetic hydrophilic molecularly imprinted resin with enhanced adsorption and recognition performance for targeted detecting chlorophenols in environmental water. Chem Eng J. 2021;420:129904. doi:10.1016/j.cej.2021.129904
Wang M, Yang C, Cao J, Yan H, Qiao F. Dual-template hydro-philic imprinted resin as an adsorbent for highly selective simultaneous extraction and determination of multiple trace plant growth regulators in red wine samples. Food Chem. 2023;411:135471. doi:10.1016/j.foodchem.2023.135471
Guo ZF, Guo TT, Guo M. Preparation of molecularly imprinted adsorptive resin for trapping of ligustrazine from the tradi-tional Chinese herb Ligusticum chuanxiong Hort. Anal Chim Acta. 2008;612(2):136-143. doi:10.1016/j.aca.2008.02.039.
Liang S, Yan H, Cao J, Han Y, Shen S, Bai L. Molecularly im-printed phloroglucinol-formaldehyde-melamine resin pre-pared in a deep eutectic solvent for selective recognition of clorprenaline and bambuterol in urine. Anal Chim Acta. 2017;951:68-77. doi:10.1016/j.aca.2016.11.009
Escribano-Ferrer E, Regué JQ, Garcia-Sala X, Montañés AB, Lamuela-Raventos RM. In vivo anti-inflammatory and antial-lergic activity of pure naringenin, naringenin chalcone, and quercetin in mice. J Nat Prod. 2019;82(2):177–182. doi:10.1021/acs.jnatprod.8b00366
Alhawiti AS, Monier M, Elsayed NH. Designing of amino func-tionalized imprinted polymeric resin for enantio-separation of (±)-mandelic acid racemate. React Funct Polymers. 2021;160:104828. doi:10.1016/j.reactfunctpolym.2021.104828
Wang Y, Zhao W, Tian X, Song H, Gao R, Tang X, Zhang X, Hao Y, Tang Y. High-efficiency recognition and detection of su-lindac in sewage using hydrophilic imprinted resorcinol-formaldehyde resin magnetic nano-spheres as SPE adsorbents combined with HPLC. Chem Eng J. 2020;392:123716. doi:10.1016/j.cej.2019.123716
Ansell RJ, Characterization of the Binding Properties of Molec-ularly Imprinted Polymers. Adv Biochem Eng Biotechnol. 2015;150:51-93. doi:10.1007/10_2015_316
Jahankhah S, Sabzehmeidani MM, Ghaedi M, Dashtian K, Ab-basi-Asl H. Hydrophilic magnetic molecularly imprinted resin in PVDF membrane for efficient selective removal of dye. J Environ Manage. 2021;300:113707. doi:10.1016/j.jenvman.2021.113707.
Petrova YY, Bulatova EV, Sevast'yanova EV, Mateyshina YG. Quercetin-imprinted monolithic polymer. Mater Today Proc. 2020;31(3):555–557. doi:10.1016/j.matpr.2020.06.213
Zhi K, Li Z, Luo H, Ding Y, Chen F, Tan Y, Liu H. Selective adsorption of quercetin by the sol-gel surface molecularly im-printed polymer. Polymers. 2023;15(4):905. doi:10.3390/polym15040905
DOI: https://doi.org/10.15826/chimtech.2023.10.3.10
Copyright (c) 2023 Yuliya Yu. Petrova, Elena V. Bulatova, Dmitry O. Zelentsov, Yuliya G. Mateyshina
This work is licensed under a Creative Commons Attribution 4.0 International License.
Chimica Techno Acta, 2014-2024
ISSN 2411-1414 (Online)
Copyright Notice