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The Synthesis of Phosphonic Acid-Functionalized Polymeric Spherical Particles by Heterogeneous Polymerization Method and Their Adsorption Properties of Metal Ions

Fernandez, Rio Benny 大阪大学

2022.03.24

概要

The heterogeneous polymerization is widely applied for producing a vast amount of polymeric particles, where emulsion and suspension polymerization are a part of such a process. As for its components, the emulsion method enables the production of oil-in- water (O/W), while the suspension method is possible to produce a water-in-oil (W/O) system. Surface-functionalized polymers have attracted widespread interest in many applications. Functionalization of polymers with functional desire groups, i.e., phosphonic acid group, are helpful in various fields such as catalyst, paint, and others.

This thesis focused on synthesizing phosphonic acid-functionalized polymeric spherical particles through either emulsion or suspension polymerization method. Obtained spherical polymer particles were applied to adsorb metal ions and study their adsorption kinetic properties.

Firstly, the synthesis of phosphonic acid-functionalized on styrene and divinylbenzene nanoparticles was successfully conducted by the O/W emulsion polymerization method. This method comprising two primary components, they are (1) the aqueous phase (water, water-soluble initiator, and functional agent) as the continuous phase and (2) the oil phase (monomer and crosslinker) as a droplet. All of the components are mixed under N2 gas at 70oC with a stirring process at 100 rpm. IR results reveal that phosphonic acid groups were successfully grafted onto polymer main chains. SEM image (Fig.1a) shows that the functionalized nanoparticles are uniform and spherical.

On the other hand, I also successfully synthesized the nanoparticle-based on styrene and divinylbenzene with a similar method. This non-functionalized polymer also shown high uniformity and spherical shape (Fig.1b).

Secondly, crosslinked poly(vinylphosphonic acid) particles were successfully synthesized using the W/O suspension polymerization method in the presence of vinylphosphonic acid as a monomer, poly(ethylene glycol) diacrylate (PEGDA) as a crosslinker, and Benzoyl peroxide (BPO) as an initiator. The PEGDA content was varied from 5% to 20 % molar ratio concerning VPA. In this term, the aqueous phase (monomer, crosslinker, stabilizer, and water) is a droplet, and the oil phase (silicone oil and oil- soluble initiator) is the continuous phase. Briefly, two separate mixtures are combined after thoroughly mixing in their respective phase under N2 gas at 65oC with a stirring process at 400 rpm. The obtained particles were characterized by IR spectroscopy, optical microscope, and SEM. The particles were polydisperse and spherical. Their sizes ranged from 10 to 200 μm, as shown in Fig.2.

In order to investigate the kinetic study on the adsorption, a batch adsorption experiment was employed to trivalent (Ln3+ = La3+, Tb3+, and Lu3+) and divalent (Cu2+ and Zn2+) metal ions. The adsorption kinetic study investigated the effect of PEGDA content, initial solution pH, contact time, and initial metal concentration to get the optimum conditions. In the preliminary study, the 10 % molar PEGDA (PVPA-10) ratio gave the highest adsorption capacity of Tb3+ ions than the others, and the adsorption was achieved at 60 min. Moreover, the adsorption of all metal ions was strongly pH- dependence due to the deprotonation of the phosphonic acid functional group on the adsorbent surface. We selected 5 x 10-5 mol L-1 as the optimum metal ions concentration for carrying out all other batch experimental studies.

Finally, this study demonstrated the determination of kinetic parameters and correlation coefficient (R2) values derived from the Lagergren equation, including pseudo-first-order (PFO) and pseudo-second-order (PFO) kinetic model to evaluate the experimental data. It was found that the adsorption fits well best, either PFO or PSO, according to the R2 values, which are high enough for both kinetic models (R2 > 0.8). However, R2 does not guarantee the model acceptability and is not sufficient to determine a suitable kinetic model. Therefore, the evaluation for residues or linear modeling adsorption kinetic errors should be done to avoid the spurious conclusion. Different validation methods were applied to calculate the errors. These validation methods including Sum of Square Error (SSE), Chi-Square (χ2), Mean Square Error (MSE), Root

Means Square Error (RMSE), Normalized Standard Deviation (∆y(%)), Average Relative Error (ARE), and Sum of Absolute Error (SAE). Each of these validation methods is a measure of how low the model error is. Consequently, the model would have higher R2 values and lower values for the other validation methods. Based on this calculation, we could say that La3+, Tb3+, Lu3+, Cu2+, and Zn2+ ions adsorbed onto PVPA-10 are better described by PFO rather than PSO kinetic model. This model indicated that one metal ion is exclusively adsorbed onto one unoccupied adsorption site on the PVPA-10 particle surface. We also tried to evaluate the mechanism of metal ions uptake onto PVPA-10 particles. The mechanism of metal ions uptake occurs either by ion exchange or adsorption or by both, depending on the charged state of the adsorbent surface. Last, the adsorption isotherms were investigated by applying Freundlich and Langmuir`s non- linear model. The maximum adsorption of La3+, Tb3+, Lu3+, Cu2+, and Zn2+ predicted using Langmuir adsorption isotherm model to be 0.185, 0.097, 0.088, 0.045, and 0.135 mmol g-1, respectively.

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Chapter I

[1] K. Naseem, Z. Hussain Farooqi, M. Zia Ur Rehman, M. Atiq Ur Rehman, and M. Ghufran, “Microgels as efficient adsorbents for the removal of pollutants from aqueous medium,” Rev. Chem. Eng., vol. 35, no. 2, pp. 285–309, 2019, doi: 10.1515/revce-2017-0042.

[2] Z. Dai and T. Ngai, “Microgel particles: The structure-property relationships and their biomedical applications,” J. Polym. Sci. Part A Polym. Chem., vol. 51, no. 14,pp. 2995–3003, 2013, doi: 10.1002/pola.26698.

[3] R. A. Meurer et al., “Biofunctional Microgel-Based Fertilizers for Controlled Foliar Delivery of Nutrients to Plants,” Angew. Chemie - Int. Ed., vol. 56, no. 26,pp. 7380–7386, 2017, doi: 10.1002/anie.201701620.

[4] R. Arshady, “Suspension, emulsion, and dispersion polymerization: A methodological survey,” Colloid Polym. Sci., vol. 270, no. 8, pp. 717–732, 1992, doi: 10.1007/BF00776142.

[5] Z. Zeng, S. Yang, L. Zhang, and D. Hua, “Phosphonate-functionalized polystyrene microspheres with controlled zeta potential for efficient uranium sorption,” RSC Adv., vol. 6, no. 78, pp. 74110–74116, 2016, doi: 10.1039/c6ra16219c.

[6] I. Komasawa, T. Otake, and Y. Higaki, “Equilibrium studies of the extraction of divalent metals from nitrate media with di-(2ethylhexyl) phosphoric acid,” J. Inorg. Nucl. Chem., vol. 43, no. 12, pp. 3351–3356, 1981, doi: 10.1016/0022-1902(81)80114-5.

[7] M. Matsumoto, K. Yoshizuka, K. Kondo, and F. Nakashio, “Extraction equilibria of copper and zinc with n-8-quinolylsulfonamides,” J. Chem. Eng. Japan, vol. 17, no. 1, pp. 89–93, 1984, doi: 10.1252/jcej.17.89.

[8] F. Zhang, J. Dai, A. Wang, and W. Wu, “Investigation of the synergistic extraction behavior between cerium (III) and two acidic organophosphorus extractants using FT-IR, NMR and mass spectrometry,” Inorganica Chim. Acta, vol. 466, pp. 333– 342, 2017, doi: 10.1016/j.ica.2017.06.016.

[9] B. J. Brennan, M. J. Llansola Portolés, P. A. Liddell, T. A. Moore, A. L. Moore, and D. Gust, “Comparison of silatrane, phosphonic acid, and carboxylic acid functional groups for attachment of porphyrin sensitizers to TiO2 in photoelectrochemical cells,” Phys. Chem. Chem. Phys., vol. 15, no. 39, pp. 16605– 16614, 2013, doi: 10.1039/c3cp52156g.

Chapter II

[1] A. Zeller et al., “Nanostructured coatings by adhesion of phosphonated polystyrene particles onto titanium surface for implant material applications,” ACS Appl. Mater. Interfaces, vol. 2, no. 8, pp. 2421–2428, 2010, doi: 10.1021/am1004305.

[2] A. Popa, C. M. Davidescu, P. Negrea, G. Ilia, A. Katsaros, and K. D. Demadis, “Synthesis and characterization of phosphonate ester/phosphonic acid grafted styrene - Divinylbenzene copolymer microbeads and their utility in adsorption of divalent metal ions in aqueous solutions,” Ind. Eng. Chem. Res., vol. 47, no. 6, pp. 2010–2017, 2008, doi: 10.1021/ie070886g.

[3] J. Florek, S. Giret, E. Juère, D. Larivière, and F. Kleitz, “Functionalization of mesoporous materials for lanthanide and actinide extraction,” Dalt. Trans., vol. 45, no. 38, pp. 14832–14854, 2016, doi: 10.1039/c6dt00474a.

[4] Y. Luo and X. Zhou, “Nanoencapsulation of a hydrophobic compound by a miniemulsion polymerization process,” J. Polym. Sci. Part A Polym. Chem., vol. 42, no. 9, pp. 2145–2154, 2004, doi: 10.1002/pola.20065.

[5] N. Bechthold, F. Tiarks, M. Willert, K. Landfester, and M. Antonietti, “Miniemulsion polymerization: Applications and new materials,” Macromol. Symp., vol. 151, pp. 549–555, 2000, doi: 10.1002/1521- 3900(200002)151:1<549::AID-MASY549>3.0.CO;2-D.

[6] X. Yang, L. W. Zhu, L. S. Wan, J. Zhang, and Z. K. Xu, “Surface functionalization of cross-linked polystyrene microspheres via thiol-ene ‘click’ reaction and assembly in honeycomb films for lectin recognition,” J. Mater. Res., vol. 28, no. 4, pp. 642–650, 2013, doi: 10.1557/jmr.2012.420.

[7] Z. Yang, H. Peng, W. Wang, and T. Liu, “Crystallization behavior of poly(ε- caprolactone)/layered double hydroxide nanocomposites,” J. Appl. Polym. Sci., vol. 116, no. 5, pp. 2658–2667, 2010, doi: 10.1002/app.

[8] G. Liu and P. Liu, “Preparation of carboxyl-coated polystyrene nanoparticles using oleic acid,” IET Nanobiotechnology, vol. 3, no. 2, pp. 23–27, 2009, doi: 10.1049/iet-nbt.2008.0009.

[9] N. M. Sekerak et al., “Size control of cross-linked carboxy-functionalized polystyrene particles: Four orders of magnitude of dimensional versatility,” Eur. Polym. J., vol. 101, no. January, pp. 202–210, 2018, doi: 10.1016/j.eurpolymj.2018.01.028.

[10] C. Dire, S. Magnet, L. Couvreur, and B. Charleux, “Nitroxide-mediated controlled/living free-radical surfactant-free emulsion polymerization of methyl methacrylate using a poly(methacrylie acid)-based macroalkoxyamine initiator,” Macromolecules, vol. 42, no. 1, pp. 95–103, 2009, doi: 10.1021/ma802083g.

[11] S. Zhu, U. Panne, and K. Rurack, “A rapid method for the assessment of the surface group density of carboxylic acid-functionalized polystyrene microparticles,” Analyst, vol. 138, no. 10, pp. 2924–2930, 2013, doi: 10.1039/c3an36578f.

[12] X. Zhang et al., “Polystyrene sulphonic acid resins with enhanced acid strength via macromolecular self-assembly within confined nanospace,” Nat. Commun., vol. 5,pp. 1–9, 2014, doi: 10.1038/ncomms4170.

[13] R. M. Pike and R. A. Cohen, “Organophosphorus Polymers . I . Peroxide-Initiated Vinylphosphonate *,” vol. X, pp. 531–538, 1960.

[14] A. Głowinska and A. W. Trochimczuk, “Polymer-supported phosphoric, phosphonic and phosphinic acids—from synthesis to properties and applications in separation processes,” Molecules, vol. 25, no. 18, 2020, doi: 10.3390/molecules25184236.

[15] B. T. Benkhaled, T. Montheil, V. Lapinte, and S. Monge, “Hydrosoluble phosphonic acid functionalized poly(2-ethyl-2-oxazoline) chelating polymers for the sorption of metallic cations,” J. Polym. Sci., vol. 58, no. 20, pp. 2875–2886, 2020, doi: 10.1002/pol.20200487.

[16] A. W. Trochimczuk, “Synthesis of functionalized phenylphosphinic acid resins through Michael reaction: Part II. Resins with multidentate ligands,” React. Funct. Polym., vol. 48, no. 1–3, pp. 141–148, 2001, doi: 10.1016/S1381-5148(01)00049-9.

[17] X. Liu, J. Li, X. Wang, C. Chen, and X. Wang, “High performance of phosphate- functionalized graphene oxide for the selective adsorption of U(VI) from acidic solution,” J. Nucl. Mater., vol. 466, pp. 56–64, 2015, doi: 10.1016/j.jnucmat.2015.07.027.

[18] C. M. Davidescu et al., “Behaviour of Polymeric Resins Bearing Various Phosphorus Containing Ligands towards Metal Ions from Aqueous Solutions,” vol. 55, no. 69, pp. 32–36, 2010.

[19] A. Hanisch, P. Yang, A. N. Kulak, L. A. Fielding, F. C. Meldrum, and S. P. Armes, “Phosphonic Acid-Functionalized Diblock Copolymer Nano-Objects via Polymerization-Induced Self-Assembly: Synthesis, Characterization, and Occlusion into Calcite Crystals,” Macromolecules, vol. 49, no. 1, pp. 192–204, 2016, doi: 10.1021/acs.macromol.5b02212.

[20] J.-S. Song, L. Chagal, and M. A. Winnik, “Monodisperse micrometer-size carboxyl-functionalized polystyrene particles obtained by two-stage dispersion polymerization,” Macromolecules, vol. 39, no. 17, pp. 5729–5737, 2006, doi: 10.1021/ma052550f.

[21] L. Breucker, K. Landfester, and A. Taden, “Phosphonic Acid-Functionalized Polyurethane Dispersions with Improved Adhesion Properties,” ACS Appl. Mater. Interfaces, vol. 7, no. 44, pp. 24641–24648, 2015, doi: 10.1021/acsami.5b06903.

[22] D. Hua, J. Tang, J. Jiangs, X. Zhu, and R. Bai, “A facile approach for preparation of phenylphosphinic acid-functionalized pst microspheres by emulsion polymerization using amphiphilic macro-RAFT agent as emulsifier,” Macromolecules, vol. 42, no. 22, pp. 8697–8701, 2009, doi: 10.1021/ma9018334.

[23] A. Ziegler, K. Landfester, and A. Musyanovych, “Synthesis of phosphonate- functionalized polystyrene and poly(methyl methacrylate) particles and their kinetic behavior in miniemulsion polymerization,” Colloid Polym. Sci., vol. 287, no. 11, pp. 1261–1271, 2009, doi: 10.1007/s00396-009-2087-z.

[24] R. Arshady, “Suspension, emulsion, and dispersion polymerization: A methodological survey,” Colloid Polym. Sci., vol. 270, no. 8, pp. 717–732, 1992, doi: 10.1007/BF00776142.

[25] C. Zhao, H. Okada, and R. Sugimoto, “Polymerization of styrene in aqueous system using a diethylzinc and 1,10-phenanthroline complex,” Polymer (Guildf)., vol. 154, no. August, pp. 211–217, 2018, doi: 10.1016/j.polymer.2018.09.019.

Chapter III

[1] B. Valerie, Alard., Garbine, Aguirre., Laurent, “Microgels for the delivery of cosmetic active organic substances,” 2019.

[2] R. E. Dey, I. Wimpenny, J. E. Gough, D. C. Watts, and P. M. Budd, “Poly(vinylphosphonic acid-co-acrylic acid) hydrogels: The effect of copolymer composition on osteoblast adhesion and proliferation,” J. Biomed. Mater. Res. - Part A, vol. 106, no. 1, pp. 255–264, 2018, doi: 10.1002/jbm.a.36234.

[3] J. A. Bonham, M. A. Faers, and J. S. Van Duijneveldt, “Non-aqueous microgel particles: Synthesis, properties and applications,” Soft Matter, vol. 10, no. 47, pp. 9384–9398, 2014, doi: 10.1039/c4sm01834f.

[4] Z. Dai and T. Ngai, “Microgel particles: The structure-property relationships and their biomedical applications,” J. Polym. Sci. Part A Polym. Chem., vol. 51, no. 14,pp. 2995–3003, 2013, doi: 10.1002/pola.26698.

[5] R. A. Meurer et al., “Biofunctional Microgel-Based Fertilizers for Controlled Foliar Delivery of Nutrients to Plants,” Angew. Chemie - Int. Ed., vol. 56, no. 26,pp. 7380–7386, 2017, doi: 10.1002/anie.201701620.

[6] K. Naseem, Z. Hussain Farooqi, M. Zia Ur Rehman, M. Atiq Ur Rehman, and M. Ghufran, “Microgels as efficient adsorbents for the removal of pollutants from aqueous medium,” Rev. Chem. Eng., vol. 35, no. 2, pp. 285–309, 2019, doi: 10.1515/revce-2017-0042.

[7] M. Ahmaruzzaman, “Industrial wastes as low-cost potential adsorbents for the treatment of wastewater laden with heavy metals,” Adv. Colloid Interface Sci., vol. 166, no. 1–2, pp. 36–59, 2011, doi: 10.1016/j.cis.2011.04.005.

[8] B. L. Rivas, E. Pereira, P. Gallegos, D. Homper, and K. E. Geckeler, “Metal ion binding capability of the water-soluble poly(vinyl phosphonic acid) for mono-, di-, and trivalent cations,” J. Appl. Polym. Sci., vol. 92, no. 5, pp. 2917–2922, 2004, doi: 10.1002/app.20246.

[9] B. Bingöl, W. H. Meyer, M. Wagner, and G. Wegner, “Synthesis, microstructure, and acidity of poly(vinylphosphonic acid),” Macromol. Rapid Commun., vol. 27, no. 20, pp. 1719–1724, 2006, doi: 10.1002/marc.200600513.

[10] B. Bingöl, C. Strandberg, A. Szabo, and G. Wegner, “Copolymers and hydrogels based on vinylphosphonic acid,” Macromolecules, vol. 41, no. 8, pp. 2785–2790, 2008, doi: 10.1021/ma702807a.

[11] A. Yuchi, T. Sato, Y. Morimoto, H. Mizuno, and H. Wada, “Adsorption Mechanism of Trivalent Metal Ions on Chelating Resins Containing Iminodiacetic Acid Groups with Reference to Selectivity,” Anal. Chem., vol. 69, no. 15, pp. 2941–2944, 1997, doi: 10.1021/ac9612685.

[12] V. Najafi et al., “Synthesis and characterization of alcogels based on ethylene glycol methyl ether methacrylate-vinyl phosphonic acid copolymers,” J. Polym. Res., vol. 19, no. 6, 2012, doi: 10.1007/s10965-012-9866-9.

[13] N. S. Kwak, H. M. Park, and T. S. Hwang, “Preparation of ion-exchangeable nanobeads using suspension polymerization and their sorption properties for indium in aqueous solution,” Chem. Eng. J., vol. 191, pp. 579–587, 2012, doi: 10.1016/j.cej.2012.03.018.

[14] N. S. Kwak, Y. Baek, and T. S. Hwang, “The synthesis of poly(vinylphosphonic acid-co-methacrylic acid) microbeads by suspension polymerization and the characterization of their indium adsorption properties,” J. Hazard. Mater., vol. 203–204, pp. 213–220, 2012, doi: 10.1016/j.jhazmat.2011.12.020.

[15] N. Sahiner, “Fast and high amount of uranyl ion uptake by p(vinyl phosphonic acid) microgels prepared by UV irradiation technique,” Water. Air. Soil Pollut., vol. 225, no. 6, pp. 1–8, 2014, doi: 10.1007/s11270-014-1982-1.

[16] I. Anil, S. T. Gunday, A. Bozkurt, and O. Alagha, “Design of crosslinked hydrogels comprising poly(Vinylphosphonic acid) and bis[2-(methacryloyloxy)ethyl] phosphate as an efficient adsorbent for wastewater dye removal,” Nanomaterials, vol. 10, no. 1, 2020, doi: 10.3390/nano10010131.

[17] B. Onghena, E. Papagni, E. R. Souza, D. Banerjee, K. Binnemans, and T. Vander Hoogerstraete, “Speciation of lanthanide ions in the organic phase after extraction from nitrate media by basic extractants,” RSC Adv., vol. 8, no. 56, pp. 32044– 32054, 2018, doi: 10.1039/c8ra06712k.

[18] H. Haraguchi, A. Itoh, C. Kimata, and H. Miwa, “Speciation of yttrium and lanthanides in natural water by inductively coupled plasma mass spectrometry after preconcentration by ultrafiltration and with a chelating resin,” Analyst, vol. 123, no. 5, pp. 773–778, 1998, doi: 10.1039/a708253c.

[19] S. D. Alexandratos, D. R. Quillen, and W. J. Mcdowell, “Bifunctional Phosphinic Acid Resins for the Complexation of Lanthanides and Actinides,” Sep. Sci. Technol., vol. 22, no. 2–3, pp. 983–995, 1987, doi: 10.1080/01496398708068994.

[20] J. Wang, “Adsorption of aqueous neodymium, europium, gadolinium, terbium, and yttrium ions onto nZVI-montmorillonite: kinetics, thermodynamic mechanism, and the influence of coexisting ions,” Environ. Sci. Pollut. Res., vol. 25, no. 33, pp. 33521–33537, 2018, doi: 10.1007/s11356-018-3296-0.

[21] T. Kegl, A. Košak, A. Lobnik, and I. Ban, “Terbium ion adsorption from aqueous solution by using magneticγ-Fe2O3-NH4OH@SiO2 nanoparticles functionalized with amino groups,” Materials (Basel)., vol. 12, no. 8, 2019, doi: 10.3390/ma12081294.

[22] R. Arshady, “Suspension, emulsion, and dispersion polymerization: A methodological survey,” Colloid Polym. Sci., vol. 270, no. 8, pp. 717–732, 1992, doi: 10.1007/BF00776142.

[23] E. Vivaldo-Lima, P. E. Wood, A. E. Hamielec, and A. Penlidis, “An Updated Review on Suspension Polymerization,” Ind. Eng. Chem. Res., vol. 36, no. 4, pp. 939–965, 1997, doi: 10.1021/ie960361g.

[24] K. Kesenci and E. Piykin, “Production of poly [ ( ethylene glycol dimethacry1ate )-co- acrylamide ] based hydrogel beads by suspension copolymerization,” vol. 391,pp. 385–391, 1997.

[25] A. Tuncel, “Suspension polymerization of poly(ethylene glycol) methacrylate: A route for swellable spherical gel beads with controlled hydrophilicity and functionality,” Colloid Polym. Sci., vol. 278, no. 12, pp. 1126–1138, 2000, doi: 10.1007/s003960000317.

[26] L. MacArie and G. Ilia, “Poly(vinylphosphonic acid) and its derivatives,” Prog.Polym. Sci., vol. 35, no. 8, pp. 1078–1092, 2010, doi: 10.1016/j.progpolymsci.2010.04.001.

[27] X. Wang, X. Ding, Z. Zheng, X. Hu, X. Cheng, and Y. Peng, “Magnetic molecularly imprinted polymer particles synthesized by suspension polymerization in silicone oil,” Macromol. Rapid Commun., vol. 27, no. 14, pp. 1180–1184, 2006, doi: 10.1002/marc.200600211.

[28] G. I. Taylor, “The formation of emulsions in definable fields of flow,” Proc. R. Soc. London. Ser. A, Contain. Pap. a Math. Phys. Character, vol. 146, no. 858, pp.501–523, 1934, doi: 10.1098/rspa.1934.0169.

[29] P. J. Dowding and B. Vincent, “Suspension polymerisation to form polymer beads,” Colloids Surfaces A Physicochem. Eng. Asp., vol. 161, no. 2, pp. 259–269, 2000, doi: 10.1016/S0927-7757(99)00375-1.

[30] S. Senel, H. Cicek, and A. Tuncel, “Production and Characterization of Poly ( ethylene glycol dimethacrylate-styrene-glycidyl methacrylate ) Microbeads,” J. Appl. Polym. Sci., vol. 67, pp. 1319–1334, 1997.

[31] B. H. Stuart, Infrared Spectroscopy: Fundamentals and Applications. 2005.

[32] B. C. Melo, F. A. A. Paulino, V. A. Cardoso, A. G. B. Pereira, A. R. Fajardo, and F. H. A. Rodrigues, “Cellulose nanowhiskers improve the methylene blue adsorption capacity of chitosan-g-poly(acrylic acid) hydrogel,” Carbohydr. Polym., vol. 181, no. October, pp. 358–367, 2018, doi: 10.1016/j.carbpol.2017.10.079.

[33] P. Dangelo et al., “Revised ionic radii of lanthanoid(III) ions in aqueous solution,”Inorg. Chem., vol. 50, no. 10, pp. 4572–4579, 2011, doi: 10.1021/ic200260r.

[34] C. Strandberg, C. Rosenauer, and G. Wegner, “Poly (vinyl phosphonic acid): Hydrodynamic properties and SEC-calibration in aqueous solution,” Macromol. Rapid Commun., vol. 31, no. 4, pp. 374–379, 2010, doi: 10.1002/marc.200900605.

[35] D. Feng, B. Bai, H. Wang, and Y. Suo, “Novel Fabrication of PAA/PVA/Yeast Superabsorbent with Interpenetrating Polymer Network for pH-Dependent Selective Adsorption of Dyes,” J. Polym. Environ., vol. 26, no. 2, pp. 567–588, 2018, doi: 10.1007/s10924-017-0972-y.

[36] A. Bashir, T. Manzoor, L. A. Malik, A. Qureashi, and A. H. Pandith, “Enhanced and Selective Adsorption of Zn(II), Pb(II), Cd(II), and Hg(II) Ions by a Dumbbell- And Flower-Shaped Potato Starch Phosphate Polymer: A Combined Experimental and DFT Calculation Study,” ACS Omega, vol. 5, no. 10, pp. 4853–4867, 2020, doi: 10.1021/acsomega.9b03607.

[37] E. A. Abdel-Galil, A. B. Ibrahim, and M. M. Abou-Mesalam, “Sorption behavior of some lanthanides on polyacrylamide stannic molybdophosphate as organic– inorganic composite,” Int. J. Ind. Chem., vol. 7, no. 3, pp. 231–240, 2016, doi: 10.1007/s40090-016-0080-1.

[38] S. Yngve, “Zur Theorie der sogenannten Adsorption EOD – Millions of books just a mouse click away ! In more than 10 European countries !,” 1898.

[39] G. Ho, Y.S, McKay, “Pseudo-secon order model for sorption processes,” Process Biochem., vol. 34, no. 5, pp. 451–465, 199AD, doi: https://doi.org/10.1016/S0032- 9592(98)00112-5.

[40] J. P. Simonin, “On the comparison of pseudo-first order and pseudo-second order rate laws in the modeling of adsorption kinetics,” Chem. Eng. J., vol. 300, pp. 254– 263, 2016, doi: 10.1016/j.cej.2016.04.079.

[41] C. R. Lee, H. S. Kim, I. H. Jang, J. H. Im, and N. G. Park, “Pseudo first-order adsorption kinetics of N719 dye on TiO2 surface,” ACS Appl. Mater. Interfaces, vol. 3, no. 6, pp. 1953–1957, 2011, doi: 10.1021/am2001696.

[42] “Coefficient-of-determination-R2 Di Bucchianico, .pdf.” .

[43] E. D. Revellame, D. L. Fortela, W. Sharp, R. Hernandez, and M. E. Zappi, “Adsorption kinetic modeling using pseudo-first order and pseudo-second order rate laws: A review,” Clean. Eng. Technol., vol. 1, no. October, p. 100032, 2020, doi: 10.1016/j.clet.2020.100032.

[44] R.-S. Wu, Feng-Chin., Tseng, Ru-Ling., Juang, “KINETIC MODELING OF LIQUID-PHASE ADSORPTION OF REACTIVE DYES AND METAL IONS ON CHITOSAN,” Water Res., vol. 35, no. 3, pp. 613–618, 2001, doi:https://doi.org/10.1016/S0043-1354(00)00307-9.

[45] J. Lin and L. Wang, “Comparison between linear and non-linear forms of pseudo- first-order and pseudo-second-order adsorption kinetic models for the removal of methylene blue by activated carbon,” Front. Environ. Sci. Eng. China, vol. 3, no. 3, pp. 320–324, 2009, doi: 10.1007/s11783-009-0030-7.

[46] I. A. W. Tan, A. L. Ahmad, and B. H. Hameed, “Adsorption of basic dye on high- surface-area activated carbon prepared from coconut husk: Equilibrium, kinetic and thermodynamic studies,” J. Hazard. Mater., vol. 154, no. 1–3, pp. 337–346, 2008, doi: 10.1016/j.jhazmat.2007.10.031.

[47] Y. Xiao, J. Azaiez, and J. M. Hill, “Erroneous Application of Pseudo-Second- Order Adsorption Kinetics Model: Ignored Assumptions and Spurious Correlations,” Ind. Eng. Chem. Res., vol. 57, no. 7, pp. 2705–2709, 2018, doi: 10.1021/acs.iecr.7b04724.

[48] B. K. Aziz, D. M. S. Shwan, and S. Kaufhold, “Characterization of Tagaran natural clay and its efficiency for removal of cadmium (II) from Sulaymaniyah industrial zone sewage,” Environ. Sci. Pollut. Res., vol. 27, no. 31, pp. 38384–38396, 2020, doi: 10.1007/s11356-019-06995-x.

[49] F. Alakhras, “Kinetic Studies on the Removal of Some Lanthanide Ions from Aqueous Solutions Using Amidoxime-Hydroxamic Acid Polymer,” J. Anal. Methods Chem., vol. 2018, 2018, doi: 10.1155/2018/4058503.

[50] K. K. Swain, P. M. Mishra, and A. P. Devi, “Biosorption of praseodymium (III) using Terminalia arjuna bark powder in batch systems: Isotherm and kinetic studies,” Water Sci. Technol., vol. 77, no. 3, pp. 727–738, 2018, doi:10.2166/wst.2017.589.

[51] G. Wójcik, “Sorption behaviors of light lanthanides(III) (La(III), Ce(III), Pr(III), Nd(III)) and Cr(III) using nitrolite,” Materials (Basel)., vol. 13, no. 10, 2020, doi: 10.3390/ma13102256.

[52] Y. Zhou, C. Yan, S. Zhou, T. Liang, and X. Wen, “Preparation of montmorillonite grafted polyacrylic acid composite and study on its adsorption properties of lanthanum ions from aqueous solution,” Environ. Sci. Pollut. Res., vol. 26, no. 10,pp. 9861–9875, 2019, doi: 10.1007/s11356-019-04422-9.

[53] Q. Zhou, H. Yang, C. Yan, W. Luo, X. Li, and J. Zhao, “Synthesis of carboxylic acid functionalized diatomite with a micro-villous surface via UV-induced graft polymerization and its adsorption properties for Lanthanum(III) ions,” Colloids Surfaces A Physicochem. Eng. Asp., vol. 501, pp. 9–16, 2016, doi: 10.1016/j.colsurfa.2016.04.030.

[54] X. Cao, Q. Wang, S. Wang, and R. Man, “Preparation of a novel polystyrene- poly(hydroxamic acid) copolymer and its adsorption properties for rare earth metal ions,” Polymers (Basel)., vol. 12, no. 9, 2020, doi: 10.3390/POLYM12091905.

[55] Z. S. Birungi and E. M. N. Chirwa, “The kinetics of uptake and recovery of lanthanum using freshwater algae as biosorbents: Comparative analysis,” Bioresour. Technol., vol. 160, pp. 43–51, 2014, doi: 10.1016/j.biortech.2014.01.033.

[56] M. Wang, X. Li, W. Hua, L. Shen, X. Yu, and X. Wang, “Electrospun Poly(acrylic acid)/Silica Hydrogel Nanofibers Scaffold for Highly Efficient Adsorption of Lanthanide Ions and Its Photoluminescence Performance,” ACS Appl. Mater. Interfaces, vol. 8, no. 36, pp. 23995–24007, 2016, doi: 10.1021/acsami.6b08294.

[57] K. Dev, R. Pathak, and G. N. Rao, “Sorption behaviour of lanthanum(III), neodymium(III), terbium(III), thorium(IV) and uranium(VI) on amberlite XAD-4 resin functionalized with bicine ligands,” Talanta, vol. 48, no. 3, pp. 579–584, 1999, doi: 10.1016/S0039-9140(98)00274-4.

[58] H. Zhang, R. G. Mcdowell, L. R. Martin, and Y. Qiang, “Selective Extraction of Heavy and Light Lanthanides from Aqueous Solution by Advanced Magnetic Nanosorbents,” ACS Appl. Mater. Interfaces, vol. 8, no. 14, pp. 9523–9531, 2016, doi: 10.1021/acsami.6b01550.

[59] Y. Wei, K. A. M. Salih, M. F. Hamza, T. Fujita, E. Rodríguez-Castellón, and E. Guibal, “Synthesis of a new phosphonate-based sorbent and characterization of its interactions with lanthanum (Iii) and terbium (iii),” Polymers (Basel)., vol. 13, no. 9, 2021, doi: 10.3390/polym13091513.

[60] D. Baybaş and U. Ulusoy, “Polyacrylamide-clinoptilolite/Y-zeolite composites: Characterization and adsorptive features for terbium,” J. Hazard. Mater., vol. 187, no. 1–3, pp. 241–249, 2011, doi: 10.1016/j.jhazmat.2011.01.014.

[61] M. M. Saeed and A. Rusheed, “Investigation of sorption of Tb(III) by 2- thenoyltrifluoroacetone supported onto polyurethane foam,” Radiochim. Acta, vol. 90, no. 1, pp. 35–42, 2002, doi: 10.1524/ract.2002.90.1_2002.35.

[62] C. Rill, Z. I. Kolar, G. Kickelbick, H. T. Wolterbeek, and J. A. Peters, “Kinetics and thermodynamics of adsorption on hydroxyapatite of the [ 160Tb]terbium complexes of the bone-targeting ligands DOTP and BPPED,” Langmuir, vol. 25, no. 4, pp. 2294–2301, 2009, doi: 10.1021/la803562e.

[63] M. R. Awual et al., “Ligand field effect for Dysprosium(III) and Lutetium(III) adsorption and EXAFS coordination with novel composite nanomaterials,” Chem.Eng. J., vol. 320, pp. 427–435, 2017, doi: 10.1016/j.cej.2017.03.075.

[64] Y. Hu, E. Drouin, D. Larivière, F. Kleitz, and F. G. Fontaine, “Highly Efficient and Selective Recovery of Rare Earth Elements Using Mesoporous Silica Functionalized by Preorganized Chelating Ligands,” ACS Appl. Mater. Interfaces, vol. 9, no. 44, pp. 38584–38593, 2017, doi: 10.1021/acsami.7b12589.

[65] Q. Qu, Q. Gu, Z. Gu, Y. Shen, C. Wang, and X. Hu, “Efficient removal of heavy metal from aqueous solution by sulfonic acid functionalized nonporous silica microspheres,” Colloids Surfaces A Physicochem. Eng. Asp., vol. 415, pp. 41–46, 2012, doi: 10.1016/j.colsurfa.2012.08.059.

[66] F. Ge, M. M. Li, H. Ye, and B. X. Zhao, “Effective removal of heavy metal ions Cd 2+, Zn 2+, Pb 2+, Cu 2+ from aqueous solution by polymer-modified magnetic nanoparticles,” J. Hazard. Mater., vol. 211–212, pp. 366–372, 2012, doi: 10.1016/j.jhazmat.2011.12.013.

[67] F. An, B. Gao, X. Dai, M. Wang, and X. Wang, “Efficient removal of heavy metal ions from aqueous solution using salicylic acid type chelate adsorbent,” J. Hazard. Mater., vol. 192, no. 3, pp. 956–962, 2011, doi: 10.1016/j.jhazmat.2011.05.050.

[68] Y. Zhu, J. Hu, and J. Wang, “Competitive adsorption of Pb(II), Cu(II) and Zn(II) onto xanthate-modified magnetic chitosan,” J. Hazard. Mater., vol. 221–222, pp. 155–161, 2012, doi: 10.1016/j.jhazmat.2012.04.026.

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