Skip to main content
Top
Published in: Colloid and Polymer Science 2/2014

01-02-2014 | Original Contribution

Magnetic and hydrophilic imprinted particles via ATRP at room temperature for selective separation of sulfamethazine

Authors: Yongli Zou, Chunyan Zhao, Jiangdong Dai, Zhiping Zhou, Jianming Pan, Ping Yu, Yongsheng Yan, Chunxiang Li

Published in: Colloid and Polymer Science | Issue 2/2014

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

In this work, a facile route to prepare hydrophilic molecularly imprinted particles with magnetic susceptibility (MMIPs) was first reported via atom transfer radical precipitation polymerization (ATRPP) in a methanol/water solvent at low temperature (298 K), which can be considered as an environment-friendly system. During the process, 2-hydroxyethyl methacrylate and N, N-methylenebisacrylamide monomers were added to improve the hydrophilicity of the polymers. The obtained materials were characterized in detail by X-ray diffraction, transform infrared spectroscopy, thermogravimetric analysis, vibrating sample magnetometer, scanning electron microscopy and transmission electron microscopy, and then used for the selective separation of sulfamethazine (SMZ) from aqueous medium. The images showed Fe3O4 nanoparticles that were successfully embedded into the polymer particles with the size ranging from 450 to 650 nm, which exhibited great superparamagnetic susceptivity and high thermal stability. Batch adsorption experiments were performed to determine specific adsorption equilibrium, kinetics, and selective recognition and separation. The effect of the ratio of the double monomers used in the adsorption property was also studied. The equilibrium data of MMIPs toward SMZ was well fitted by the Langmuir isotherm model, and the maximum adsorption capacity estimated was 66.67 μmol g−1. The adsorption kinetics rapidly achieved equilibrium within 1.0 h and was well described by the pseudo-second-order model. The MMIPs synthesized showed outstanding affinity and selectivity toward SMZ over structurally analogous antibiotics and easily achieved magnetic separation under an external magnetic field. In addition, the adsorption performance of the resulting MMIPs was no obviously decreased at least six repeated cycles.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference Wulff G (2002) Enzyme-like catalysis by molecularly imprinted polymers. Chem Rev 102:1–27CrossRef Wulff G (2002) Enzyme-like catalysis by molecularly imprinted polymers. Chem Rev 102:1–27CrossRef
2.
go back to reference Chen ZY, Xu L, Liang Y, Zhao MP (2010) PH-Sensitive water-soluble nanospheric imprinted hydrogels prepared as horseradish peroxidase mimetic enzymes. Adv Mater 22:1488–1492CrossRef Chen ZY, Xu L, Liang Y, Zhao MP (2010) PH-Sensitive water-soluble nanospheric imprinted hydrogels prepared as horseradish peroxidase mimetic enzymes. Adv Mater 22:1488–1492CrossRef
3.
go back to reference Shen XT, Zhu LH, Li J, Tang HQ (2007) Synthesis of molecular imprinted polymer coated photocatalysts with high selectivity. Chem Commun 11:1163–1165CrossRef Shen XT, Zhu LH, Li J, Tang HQ (2007) Synthesis of molecular imprinted polymer coated photocatalysts with high selectivity. Chem Commun 11:1163–1165CrossRef
4.
go back to reference Matsui J, Sodeyama T, Saiki Y, Miyazawa T, Yamada T, Tamaki K, Murashima T (2009) Face-to-face porphyrin moieties assembled with spacing for pyrazine recognition in molecularly imprinted polymers. Biosens Bioelectron 25:635–639CrossRef Matsui J, Sodeyama T, Saiki Y, Miyazawa T, Yamada T, Tamaki K, Murashima T (2009) Face-to-face porphyrin moieties assembled with spacing for pyrazine recognition in molecularly imprinted polymers. Biosens Bioelectron 25:635–639CrossRef
5.
go back to reference Basabe-Desmonts L, Reinhoudt DN, Crego-Calama M (2007) Design of fluorescent materials for chemical sensing. Chem Soc Rev 36:993–1017CrossRef Basabe-Desmonts L, Reinhoudt DN, Crego-Calama M (2007) Design of fluorescent materials for chemical sensing. Chem Soc Rev 36:993–1017CrossRef
6.
go back to reference Mullett WM, Martin P, Pawliszyn J (2001) In-tube molecularly imprinted polymer solid-phase microextraction for the selective determination of propranolol. Anal Chem 73:2383–2389CrossRef Mullett WM, Martin P, Pawliszyn J (2001) In-tube molecularly imprinted polymer solid-phase microextraction for the selective determination of propranolol. Anal Chem 73:2383–2389CrossRef
7.
go back to reference Ariffin MM, Miller EI, Cormack PAG, Anderson RA (2007) Molecularly imprinted solid-phase extraction of diazepam and its metabolites from hair samples. Anal Chem 79:256–262CrossRef Ariffin MM, Miller EI, Cormack PAG, Anderson RA (2007) Molecularly imprinted solid-phase extraction of diazepam and its metabolites from hair samples. Anal Chem 79:256–262CrossRef
8.
go back to reference Yin JF, Yang GL, Chen Y (2005) Rapid and efficient chiral separation of nateglinide and its l-enantiomer on monolithic molecularly imprinted polymers. J Chromatogr A 1090:68–75CrossRef Yin JF, Yang GL, Chen Y (2005) Rapid and efficient chiral separation of nateglinide and its l-enantiomer on monolithic molecularly imprinted polymers. J Chromatogr A 1090:68–75CrossRef
9.
go back to reference Zhang W, Qin L, He XW, Li WY, Zhang YK (2009) Novel surface modified molecularly imprinted polymer using acryloyl-β-cyclodextrin and acrylamide as monomers for selective recognition of lysozyme in aqueous solution. J Chromatogr A 1216:4560–4567CrossRef Zhang W, Qin L, He XW, Li WY, Zhang YK (2009) Novel surface modified molecularly imprinted polymer using acryloyl-β-cyclodextrin and acrylamide as monomers for selective recognition of lysozyme in aqueous solution. J Chromatogr A 1216:4560–4567CrossRef
10.
go back to reference Beltran A, Borrull F, Marcé RM, Cormack PAG (2010) Molecularly-imprinted polymers: useful sorbents for selective extractions. TrAC Trends Anal Chem 29:1363–1375CrossRef Beltran A, Borrull F, Marcé RM, Cormack PAG (2010) Molecularly-imprinted polymers: useful sorbents for selective extractions. TrAC Trends Anal Chem 29:1363–1375CrossRef
11.
go back to reference Tamayo FG, Turiel E, Martín-Esteban A (2007) Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: recent developments and future trends. J Chromatogr A 1152:32–40CrossRef Tamayo FG, Turiel E, Martín-Esteban A (2007) Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: recent developments and future trends. J Chromatogr A 1152:32–40CrossRef
12.
go back to reference Sellergren B (1994) Direct drug determination by selective sample enrichment on an imprinted polymer. Anal Chem 66:1578–1582CrossRef Sellergren B (1994) Direct drug determination by selective sample enrichment on an imprinted polymer. Anal Chem 66:1578–1582CrossRef
13.
go back to reference Pérez-Moral N, Mayes AG (2004) Comparative study of imprinted polymer particles prepared by different polymerization methods. Anal Chim Acta 504:15–21CrossRef Pérez-Moral N, Mayes AG (2004) Comparative study of imprinted polymer particles prepared by different polymerization methods. Anal Chim Acta 504:15–21CrossRef
14.
go back to reference Ye L, Mosbach K (2001) Molecularly imprinted microspheres as antibody binding mimics. React Funct Polym 48:149–157CrossRef Ye L, Mosbach K (2001) Molecularly imprinted microspheres as antibody binding mimics. React Funct Polym 48:149–157CrossRef
15.
go back to reference Wang JF, Cormack PAG, Sherrington DC, Khoshdel E (2003) Monodisperse molecularly imprinted polymer microspheres prepared by precipitation polymerization for affinity separation applications. Angew Chem Int Ed 42:5336–5338CrossRef Wang JF, Cormack PAG, Sherrington DC, Khoshdel E (2003) Monodisperse molecularly imprinted polymer microspheres prepared by precipitation polymerization for affinity separation applications. Angew Chem Int Ed 42:5336–5338CrossRef
16.
go back to reference Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinted technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942CrossRef Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinted technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942CrossRef
17.
go back to reference Zu BY, Pan GQ, Guo XZ, Zhang Y, Zhang HQ (2009) Preparation of molecularly imprinted polymer microspheres via atom transfer radical precipitation polymerization. J Polym Sci Part A Polym Chem 47:3257–3270CrossRef Zu BY, Pan GQ, Guo XZ, Zhang Y, Zhang HQ (2009) Preparation of molecularly imprinted polymer microspheres via atom transfer radical precipitation polymerization. J Polym Sci Part A Polym Chem 47:3257–3270CrossRef
18.
go back to reference Matyjaszewski K, Xia J (2001) Atom transfer radical polymerization. Chem Rev 101:2921–2990CrossRef Matyjaszewski K, Xia J (2001) Atom transfer radical polymerization. Chem Rev 101:2921–2990CrossRef
19.
go back to reference Zu BY, Pan GQ, Guo XZ, Zhang Y, Zhang HQ (2010) Preparation of molecularly imprinted polymers via atom transfer radical “bulk” polymerization. J Polym Sci Part A Polym Chem 48:532–541CrossRef Zu BY, Pan GQ, Guo XZ, Zhang Y, Zhang HQ (2010) Preparation of molecularly imprinted polymers via atom transfer radical “bulk” polymerization. J Polym Sci Part A Polym Chem 48:532–541CrossRef
20.
go back to reference Sasaki S, Ooya T, Takeuchi T (2010) Highly selective bisphenol A-imprinted polymers prepared by atom transfer radical polymerization. Polym Chem 1:1684–1688CrossRef Sasaki S, Ooya T, Takeuchi T (2010) Highly selective bisphenol A-imprinted polymers prepared by atom transfer radical polymerization. Polym Chem 1:1684–1688CrossRef
21.
go back to reference Gai QQ, Qua F, Zhang T, Zhang YK (2011) The preparation of bovine serum albumin surface-imprinted superparamagnetic polymer with the assistance of basic functional monomer and its application for protein separation. J Chromatogr A 1218:3489–3495CrossRef Gai QQ, Qua F, Zhang T, Zhang YK (2011) The preparation of bovine serum albumin surface-imprinted superparamagnetic polymer with the assistance of basic functional monomer and its application for protein separation. J Chromatogr A 1218:3489–3495CrossRef
22.
go back to reference Wei X, Husson SM (2005) Surface molecular imprinting by atom transfer radical polymerization. Biomacromolecules 6:1113–1121CrossRef Wei X, Husson SM (2005) Surface molecular imprinting by atom transfer radical polymerization. Biomacromolecules 6:1113–1121CrossRef
23.
go back to reference Lu CH, Wang Y, Li Y, Yang HH, Chen X, Wang XR (2009) Bifunctional superparamagnetic surface molecularly imprinted polymer core-shell nanoparticles. J Mater Chem 19:1077–1079CrossRef Lu CH, Wang Y, Li Y, Yang HH, Chen X, Wang XR (2009) Bifunctional superparamagnetic surface molecularly imprinted polymer core-shell nanoparticles. J Mater Chem 19:1077–1079CrossRef
24.
go back to reference Wei X, Husson SM (2007) Surface-grafted molecularly imprinted polymers grown from silica gel for chromatographic separations. Ind Eng Chem Res 46:2117–2124CrossRef Wei X, Husson SM (2007) Surface-grafted molecularly imprinted polymers grown from silica gel for chromatographic separations. Ind Eng Chem Res 46:2117–2124CrossRef
25.
go back to reference Laurent S, Forge D, Port M, Roch A, Robic C, Elst LV, Muller RN (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem Rev 108:2064–2110CrossRef Laurent S, Forge D, Port M, Roch A, Robic C, Elst LV, Muller RN (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem Rev 108:2064–2110CrossRef
26.
go back to reference Arteaga KA, Rodriguez JA, Miranda JM, Medina J, Barrado E (2010) Determination of non-steroidal anti-inflammatory drugs in wastewaters by magnetic matrix solid phase dispersion-HPLC. Talanta 80:1152–1157CrossRef Arteaga KA, Rodriguez JA, Miranda JM, Medina J, Barrado E (2010) Determination of non-steroidal anti-inflammatory drugs in wastewaters by magnetic matrix solid phase dispersion-HPLC. Talanta 80:1152–1157CrossRef
27.
go back to reference Zhang Y, Liu RJ, Hu YL, Li GK (2009) Microwave heating in preparation of magnetic molecularly imprinted polymer beads for trace triazines analysis in complicated samples. Anal Chem 81:967–976CrossRef Zhang Y, Liu RJ, Hu YL, Li GK (2009) Microwave heating in preparation of magnetic molecularly imprinted polymer beads for trace triazines analysis in complicated samples. Anal Chem 81:967–976CrossRef
28.
go back to reference Sarmah AK, Meyer MT, Boxall ABA (2006) A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment. Chemosphere 65:725–759CrossRef Sarmah AK, Meyer MT, Boxall ABA (2006) A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment. Chemosphere 65:725–759CrossRef
29.
go back to reference Halling-Sørensen B, Nors-Nielsen S, Lanzky PF, Ingerslev F, Holten-Lützhøft HC, Jørgensen SE (1998) Occurrence, fate, and effects of pharmaceutical substances in the environment a review. Chemosphere 36:357–393CrossRef Halling-Sørensen B, Nors-Nielsen S, Lanzky PF, Ingerslev F, Holten-Lützhøft HC, Jørgensen SE (1998) Occurrence, fate, and effects of pharmaceutical substances in the environment a review. Chemosphere 36:357–393CrossRef
30.
go back to reference Martinez JL (2008) Antibiotics and antibiotic resistance genes in natural environments. Science 321:365–367CrossRef Martinez JL (2008) Antibiotics and antibiotic resistance genes in natural environments. Science 321:365–367CrossRef
31.
go back to reference Hu YL, Li YW, Liu RJ, Tan W, Li GK (2011) Magnetic molecularly imprinted polymer beads prepared by microwave heating for selective enrichment of β-agonists in pork and pig liver samples. Talanta 84:462–470CrossRef Hu YL, Li YW, Liu RJ, Tan W, Li GK (2011) Magnetic molecularly imprinted polymer beads prepared by microwave heating for selective enrichment of β-agonists in pork and pig liver samples. Talanta 84:462–470CrossRef
32.
go back to reference Zheng N, Li YZ, Chang WB, Wang ZM, Li TJ (2002) Sulfonamide imprinted polymers using co-functional monomers. Anal Chim Acta 452:277–283CrossRef Zheng N, Li YZ, Chang WB, Wang ZM, Li TJ (2002) Sulfonamide imprinted polymers using co-functional monomers. Anal Chim Acta 452:277–283CrossRef
33.
go back to reference Matyjaszewski K (1999) Copper (I)-catalyzed atom transfer radical polymerization. Acc Chem Res 32:895–903CrossRef Matyjaszewski K (1999) Copper (I)-catalyzed atom transfer radical polymerization. Acc Chem Res 32:895–903CrossRef
34.
go back to reference Robinson KL, Khan MA, de Paz Báňez MV, Wang XS, Armes SP (2001) Controlled polymerization of 2-hydroxyethyl methacrylate by aTRP at ambient temperature. Macromolecules 34:3155–3158CrossRef Robinson KL, Khan MA, de Paz Báňez MV, Wang XS, Armes SP (2001) Controlled polymerization of 2-hydroxyethyl methacrylate by aTRP at ambient temperature. Macromolecules 34:3155–3158CrossRef
35.
go back to reference Wan WM, Pan CY (2007) Atom transfer radical dispersion polymerization in an ethanol/water mixture. Macromolecules 40:8897–8905CrossRef Wan WM, Pan CY (2007) Atom transfer radical dispersion polymerization in an ethanol/water mixture. Macromolecules 40:8897–8905CrossRef
36.
go back to reference Du BY, Mei AX, Tao PJ, Zhao B, Cao Z, Nie JJ (2009) Poly[N-isopropylacrylaminde-co −3(trimethoxysilyl)-propylmethacrylate] coated aqueous dispersed thermosensitive Fe3O4 nanoparticle. J Phys Chem C 113:10090–10096CrossRef Du BY, Mei AX, Tao PJ, Zhao B, Cao Z, Nie JJ (2009) Poly[N-isopropylacrylaminde-co −3(trimethoxysilyl)-propylmethacrylate] coated aqueous dispersed thermosensitive Fe3O4 nanoparticle. J Phys Chem C 113:10090–10096CrossRef
37.
go back to reference Yoshimatsu K, Reimhult K, Krozer A, Mosbach K, Sode K, Ye L (2007) Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization: the control of particle size suitable for different analytical applications. Anal Chim Acta 584:112–121CrossRef Yoshimatsu K, Reimhult K, Krozer A, Mosbach K, Sode K, Ye L (2007) Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization: the control of particle size suitable for different analytical applications. Anal Chim Acta 584:112–121CrossRef
38.
go back to reference Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403CrossRef Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403CrossRef
39.
go back to reference Umpleby RJ II, Baxter SC, Rampey AM, Rushton GT, Chen Y, Shimizu KD (2004) Characterization of the heterogeneous binding site affinity distributions in molecularly imprinted polymers. J Chromatogr B 804:141–149CrossRef Umpleby RJ II, Baxter SC, Rampey AM, Rushton GT, Chen Y, Shimizu KD (2004) Characterization of the heterogeneous binding site affinity distributions in molecularly imprinted polymers. J Chromatogr B 804:141–149CrossRef
40.
go back to reference Valtchev M, Palm BS, Schiller M, Steinfeld U (2009) Development of sulfamethoxazole-imprinted polymers for the selective extraction from waters. J Hazard Mater 170:722–728CrossRef Valtchev M, Palm BS, Schiller M, Steinfeld U (2009) Development of sulfamethoxazole-imprinted polymers for the selective extraction from waters. J Hazard Mater 170:722–728CrossRef
41.
go back to reference Shi XZ, Meng Y, Liu JH, Sun AL, Li DX, Yao CX, Lu Y, Chen J (2011) Group-selective molecularly imprinted polymer solid-phase extraction for the simultaneous determination of six sulfonamides in aquaculture products. Journal of Chromatography B 879:1071–1076CrossRef Shi XZ, Meng Y, Liu JH, Sun AL, Li DX, Yao CX, Lu Y, Chen J (2011) Group-selective molecularly imprinted polymer solid-phase extraction for the simultaneous determination of six sulfonamides in aquaculture products. Journal of Chromatography B 879:1071–1076CrossRef
42.
go back to reference Ho YS, McKay G (1999) The sorption of lead (II) ions on peat. Water Res 33:578–584CrossRef Ho YS, McKay G (1999) The sorption of lead (II) ions on peat. Water Res 33:578–584CrossRef
43.
go back to reference Ho YS, McKay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465CrossRef Ho YS, McKay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465CrossRef
44.
go back to reference Baydemir G, Andac M, Bereli N, Say R, Denizli A (2007) Selective removal of bilirubin from human plasma with bilirubin-imprinted particles. Ind Eng Chem Res 46:2843–2852CrossRef Baydemir G, Andac M, Bereli N, Say R, Denizli A (2007) Selective removal of bilirubin from human plasma with bilirubin-imprinted particles. Ind Eng Chem Res 46:2843–2852CrossRef
Metadata
Title
Magnetic and hydrophilic imprinted particles via ATRP at room temperature for selective separation of sulfamethazine
Authors
Yongli Zou
Chunyan Zhao
Jiangdong Dai
Zhiping Zhou
Jianming Pan
Ping Yu
Yongsheng Yan
Chunxiang Li
Publication date
01-02-2014
Publisher
Springer Berlin Heidelberg
Published in
Colloid and Polymer Science / Issue 2/2014
Print ISSN: 0303-402X
Electronic ISSN: 1435-1536
DOI
https://doi.org/10.1007/s00396-013-3072-0

Other articles of this Issue 2/2014

Colloid and Polymer Science 2/2014 Go to the issue

Premium Partners