Abstract
A surface molecular-imprinting system was developed on polypropylene (PP) fiber for melamine (Mel) as an N-containing template. In this article, acrylic acid was introduced onto the surface of PP for template binding. Subsequently, binding sites on PP were stabilized by crosslinking with ethylene glycol diglycidyl ether in the presence of Mel. The imprinted fiber (MIF-Mel) prepared with the optimal 15 % crosslinking density showed best-imprinting effect, with an imprinting factor of 2.18 respect to nonimprinted fiber, and a relative selectivity coefficient k′ of 10.40 for Mel with respect to its structural analog 2,4-dinitroaniline. MIF-Mel showed higher affinity to Mel with the maximum adsorption capacity of 15.5 mg g−1, while that on nonimprinted fiber was only 6.9 mg g−1. Its adsorption isotherm was well described using Langmuir model. Kinetic studies showed a rapid-binding interaction and high affinity of the MIF-Mel for its template, with a 2.5 times higher in binding amount and 4.7 times faster in binding speed than those of granular molecular-imprinting polymer with the same chemical structure. High degree of fitness with pseudo-second-order model revealed chemisorption was the rate-controlling step in the template-binding process. Basic theory of matrix–template interaction in this imprinting system was clarified to be dominated by electrostatic force synergized by hydrogen bonding between deprotonated carboxyl groups and protonated N atom in the template. It suggests that extension of this novel approach or theory to other imprinting system involving nitrogenous templates is very likely.
Similar content being viewed by others
References
Sibrian-Vazquez M, Spivak DA (2004) Molecular imprinting made easy. J Am Chem Soc 126:7827–7833
Ansell R (2005) Molecularly imprinted polymers for the enantioseparation of chiral drugs. Adv Drug Deliv Rev 57:1809–1835
Greene NT, Morgan SL, Shimizu KD (2004) Molecularly imprinted polymer sensor arrays. Chem Commun 10:1172–1173
Ramström O, Mosbach K (1999) Synthesis and catalysis by molecularly imprinted materials. Curr Opin Chem Biol 3:759–764
Wulff G (2002) Enzyme-like catalysis by molecularly imprinted polymers. Chem Rev 102:1–27
Balamurugan K, Gokulakrishnan K, Prakasam T (2011) Preparation and evaluation of molecularly imprinted polymer liquid chromatography column for the separation of ephedrine enantiomers. Arab J Chem 2:77
Yang H–H, Zhang S-Q, Yang W, Chen X-L, Zhuang Z-X, Xu J-G, Wang X-R (2004) Molecularly imprinted sol–gel nanotubes membrane for biochemical separations. J Am Chem Soc 126:4054–4055
Cunliffe D, Kirby A, Alexander C (2005) Molecularly imprinted drug delivery systems. Adv Drug Deliv Rev 57:1836–1853
Wei X, Li X, Husson SM (2005) Surface molecular imprinting by atom transfer radical polymerization. Biomacromolecules 6:1113–1121
Kempe H, Kempe M (2004) Novel method for the synthesis of molecularly imprinted polymer bead libraries. Macromol Rapid Commun 25:315–320
Ye L, Mosbach K (2001) Molecularly imprinted microspheres as antibody binding mimics. React Funct Polym 48:149–157
Hirayama K, Sakai Y, Kameoka K (2001) Synthesis of polymer particles with specific lysozyme recognition sites by a molecular imprinting technique. J Appl Polym Sci 81:3378–3387
Strikovsky A, Hradil J, Wulff G (2003) Catalytically active, molecularly imprinted polymers in bead form. React Funct Polym 54:49–61
Lepinay S, Kham K, Millot MC, Carbonnier B (2012) In-situ polymerized molecularly imprinted polymeric thin films used as sensing layers in surface plasmon resonance sensors: mini-review focused on 2010-2011. Chem Pap 66:340–351
Das K, Penelle J, Rotello VM (2003) Selective picomolar detection of hexachlorobenzene in water using a quartz crystal microbalance coated with a molecularly imprinted polymer thin film. Langmuir 19:3921–3925
Huang HC, Lin CI, Joseph AK, Lee YD (1027) Photo-lithographically impregnated and molecularly imprinted polymer thin film for biosensor applications. J Chromatoge A 2004:263–268
Duffy DJ, Das K, Hsu SL, Penelle J, Rotello VM, Stidham HD (2002) Binding efficiency and transport properties of molecularly imprinted polymer thin films. J Am Chem Soc 124:8290–8296
Gauczinski J, Liu Z, Zhang X, Schönhoff M (2012) Surface molecular imprinting in layer-by-layer films on silica particles. Langmuir 28:4267–4273
Yan W, Gao R, Zhang Z, Wang Q, Jiang CV, Yan C (2003) Capillary electrochromatographic separation of ionizable compounds with a molecular imprinted monolithic cationic exchange column. J Sep Sci 26:555–561
Schweitz L, Andersson LI, Nilsson S (1997) Capillary electrochromatography with molecular imprint-based selectivity for enantiomer separation of local anaesthetics. J Chromatoge A 792:401–409
Che A-F, Wan L-S, Ling J, Liu Z-M, Xu Z-K (2009) Recognition mechanism of theophylline-imprinted polymers: two-dimensional infrared analysis and density functional theory study. J Phys Chem B 113:7053–7058
Özacar M, Şengil İA (2003) Adsorption of reactive dyes on calcined alunite from aqueous solutions. J Hazard Mater 98:211–224
Skorik Y (2012) Carboxyethylated polyaminostyrene for selective copper removal. Polym Bull 68:1065–1078
Vorderbruggen MA, Wu K, Breneman CM (1996) Use of cationic aerosol photopolymerization to form silicone microbeads in the presence of molecular templates. Chem Mater 8:1106–1111
Ran D, Wang Y, Jia X, Nie C (2012) Bovine serum albumin recognition via thermosensitive molecular imprinted macroporous hydrogels prepared at two different temperatures. Anal Chim Acta 723:45–53
Rostamizadeh K, Vahedpour M, Bozorgi S (2012) Synthesis, characterization and evaluation of computationally designed nanoparticles of molecular imprinted polymers as drug delivery systems. Int J Pharm 424:67–75
Ersöz A, Say R, Denizli A (2004) Ni(II) ion-imprinted solid-phase extraction and preconcentration in aqueous solutions by packed-bed columns. Anal Chim Acta 502:91–97
Cao Q, Zhao H, Zeng L, Wang J, Wang R, Qiu X, He Y (2009) Electrochemical determination of melamine using oligonucleotides modified gold electrodes. Talanta 80:484–488
Nityanandi D, Subbhuraam CV (2009) Kinetics and thermodynamic of adsorption of chromium(VI) from aqueous solution using puresorbe. J Hazard Mater 170:876–882
Cheng HC (2004) The influence of cooperativity on the determination of dissociation constants: examination of the Cheng–Prusoff equation, the Scatchard analysis, the Schild analysis and related power equations. Pharmacol Res 50:21–40
Ying X, Cheng G, Li X (2011) The imprinting induce-fit model of specific rebinding of macromolecularly imprinted polymer microspheres. J Appl Polym Sci 122:1847–1856
Patachia S, Croitoru C (2011) Imprinted poly (vinyl alcohol) as a promising tool for xanthine derivatives separation. J Appl Polym Sci 122:2081–2089
Tseng R-L, Wu F-C, Juang R-S (2010) Characteristics and applications of the Lagergren’s first-order equation for adsorption kinetics. J Taiwan Inst Chem E 41:661–669
Ho YS, McKay G (1999) The sorption of lead(II) ions on peat. Water Res 33:578–584
Ho YS, McKay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465
Özacar M, Şengil İA, Türkmenler H (2008) Equilibrium and kinetic data, and adsorption mechanism for adsorption of lead onto valonia tannin resin. Chem Eng J 143:32–42
Li T, Chen S, Li H, Li Q, Wu L (2011) Preparation of an ion-imprinted fiber for the selective removal of Cu2+. Langmuir 27:6753–6758
Chiou M-S, Li H-Y (2002) Equilibrium and kinetic modeling of adsorption of reactive dye on cross-linked chitosan beads. J Hazard Mater 93:233–248
Yang H–H, Zhang S-Q, Tan F, Zhuang Z-X, Wang X-R (2005) Surface molecularly imprinted nanowires for biorecognition. J Am Chem Soc 127:1378–1379
Lu C-H, Zhou W-H, Han B, Yang H–H, Chen X, Wang X-R (2007) Surface-imprinted core–shell nanoparticles for sorbent assays. Anal Chem 79:5457–5461
Acknowledgements
The authors gratefully acknowledge the financial support provided by the National Natural Science Foundation of China (Grant No. 51173211), Science and Technology Project of Guangdong Province (2011B090400030), Science and Technology Project of Zhuhai (2010B050102024).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Xu, X., Chen, S., Zhuang, L. et al. Establishment of a novel surface-imprinting system for melamine recognition and mechanism of template–matrix interactions. J Mater Sci 49, 2853–2863 (2014). https://doi.org/10.1007/s10853-013-7991-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-013-7991-4