Abstract
Radiation grafting of two tertiary amine methacrylates; 2-(dimethylamino)ethyl methacrylate (DMAEMA) and 2-(diethylamino)ethyl methacrylate (DEAEMA) onto polyolefin non-woven fabric (PE/PP-NWF) was comparatively investigated in this study. In addition, the absorbent preparation process, grafting kinetics, and mechanism were investigated. The thermal properties were investigated by thermogravimetric analysis (TGA) and differential scanning calorimeter (DSC). Fourier transform infrared (FTIR) spectroscopy was performed to confirm the successful grafting and incorporation of the two monomers functional groups onto PE/PP-NWF. X-ray diffraction (XRD) analysis was used to examine the differences between the crystal sizes and structures. Lastly, the adsorption of Th(IV) ion was investigated in batch mode. The results indicate that the radiation grafting of both DMAEMA and DEAEMA onto PE/PP-NWF required high activation energies with increasing temperatures from 313 to 333 K. Furthermore, P-DMAEMA and P-DEAEMA demonstrated different adsorption behaviours towards Th(IV). Results showed that P-DEAEMA exhibited lower Th(IV) adsorption capacity compared to P-DMAEMA, although both contain similar carbonyl and tertiary amino functional groups. These findings indicate that the molecular structure of the adsorbent was responsible. The molecular sizes increased with increasing branched carbon chains from the methyl to ethyl groups. Density functional theory (DFT) analysis indicated that induced steric effect eventually increases the inter-molecular repulsions caused by the additional CH2-groups in the structure, which reduces adsorption capacity.
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References
Abdiani M, Abouzari-Lotf E, Ting TM, Nia PM, Sha’rani SS, Shockravi A, Ahmad A (2019) Novel polyolefin-based alkaline polymer electrolyte membrane for vanadium redox flow batteries. J Power Sour 424:245–253
Othman N, Selambakkannu S, Ting T, Zulhairun A (2019) Modification of kenaf fibres by single-step radiation functionalization of 2-hydroxyl methacrylate phosphoric acid (2-HMPA). SN Appl Sci 1(3):220
Othman NAF, Ahmad Sobri NS, Lias K, Tuan Abdullah TA (2015) Preparation of a novel 1-vinylimidazole/2-hydroxyethyl methacrylate grafted polyethylene terephthalate/kenaf adsorbent via radiation-induced graft copolymerization. Adv Environ Biol 9(13):53–57
Azwin Shukri N, Ghazali Z, Othman NAF, Wahit MU (2015) The effect of process parameter for graft copolymerization of sorbic acid onto polypropylene film by full factorial experimental design. Adv Environ Biol 9(13):33–38
Hayashi N, Chen J, Seko N (2018) Nitrogen-containing fabric adsorbents prepared by radiation grafting for removal of chromium from wastewater. Polymers 10(7):744
Bhardwaj Y, Tamada M, Nho Y-C, Nasef M, Güven O (2014) Harmonized protocol for radiation-induced grafting. In: Workshop on harmonized radiation graft protocol. http://www-naweb.iaea.org/napc/iachem/working_materials/Graftingprotocol.pdf. Accessed 01 Oct 2019
Bhattacharya A, Misra B (2004) Grafting: a versatile means to modify polymers: techniques, factors and applications. Prog Polym Sci 29(8):767–814
Xu J, Zhou L, Jia Y, Liu Z, Adesina AA (2015) Adsorption of thorium (IV) ions from aqueous solution by magnetic chitosan resins modified with triethylene-tetramine. J Radioanal Nucl Chem 303(1):347–356
Sadeek SA, Moussa EM, El-Sayed MA, Amine MM, Abd El-Magied MO (2014) Uranium (VI) and thorium (IV) adsorption studies on chelating resin containing pentaethylenehexamine as a functional group. J Disper Sci Technol 35(7):926–933
Donia AM, Atia AA, Amer TE, El-Hazek MN, Ismael MH (2011) Selective separation of uranium (VI), thorium (IV), and lanthanum (III) from their aqueous solutions using a chelating resin containing amine functionality. J Disper Sci Technol 32(11):1673–1681
Yu X, Wei C, Wu H (2015) Effect of molecular structure on the adsorption behaviour of cationic dyes onto natural vermiculite. Sep Purif Technol 156:489–495
Kavaklı C, Kavaklı PA, Turan BD, Hamurcu A, Güven O (2014) Quaternized dimethylaminoethyl methacrylate strong base anion exchange fibres for as (V) adsorption. Radiat Phys Chem 102:84–95
Yamada K, Ishiguro Y, Kimura Y, Asamoto H, Minamisawa H (2019) Two-step grafting of 2-hydroxyethyl methacrylate (HEMA) and 2-(dimethylamino) ethyl methacrylate (DMAEMA) onto a polyethylene plate for enhancement of Cr(VI) ion adsorption. Environ Technol 40(7):855–869
Ma H-L, Zhang Y, Zhang L, Wang L, Sun C, Liu P, He L, Zeng X, Zhai M (2016) Radiation-induced graft copolymerization of dimethylaminoethyl methacrylate onto graphene oxide for Cr(VI) removal. Radiat Phys Chem 124:159–163. https://doi.org/10.1016/j.radphyschem.2015.11.002
Liu X, Ao J, Yang X, Ling C, Zhang B, Wang Z, Yu M, Shen R, Ma H, Li J (2017) Green and efficient synthesis of an adsorbent fiber by preirradiation-induced grafting of PDMAEMA and its Au(III) adsorption and reduction performance. J Appl Polym Sci. 134(25):1–11
Bai Y, Liang YN, Hu X (2017) An eco-friendly approach for heavy metal adsorbent regeneration using CO2-responsive molecular octopus. Chemosphere 185:1157–1163. https://doi.org/10.1016/j.chemosphere.2017.07.086
Cong Y, Chen K, Zhou S, Wu L (2015) Synthesis of pH and UV dual-responsive microcapsules with high loading capacity and their application in self-healing hydrophobic coatings. J Mater Chem A 3(37):19093–19099
Zhou Y, Laura DN, Rigoletto Jr R, Moore DJ, Foltis LC (2011) Method of Protecting Dyed Hair Color from Fading or Wash-Out. Google Patents
Wang SJ, Chen Z, Jacobsen JR, Willett PS, Yarusso DJ, Soyoung K (2016) Adhesive composition. Google Patents
Selambakkannu S, Othman NAF, Bakar KA, Karim ZA (2019) Adsorption studies of packed bed column for the removal of dyes using amine functionalized radiation-induced grafted fibre. SN Appl Sci 1(2):175
Selambakkannu S, Othman NAF, Bakar KA, Shukor SA, Karim ZA (2018) A kinetic and mechanistic study of adsorptive removal of metal ions by imidazole-functionalized polymer graft banana fibre. Radiat Phys Chem 153:58–69
Madrid JF, Barsbay M, Abad L, Güven O (2016) Grafting of N, N-dimethylaminoethyl methacrylate from PE/PP nonwoven fabric via radiation-induced RAFT polymerization and quaternization of the grafts. Radiat Phys Chem 124:145–154
Sithambaranathan P, Nasef M, Ahmad A, Ripin A (2017) Crosslinked composite membrane by radiation grafting of 4-vinylpyridine/triallyl-cyanurate mixtures onto poly (ethylene-co-tetrafluoroethylene) and phosphoric acid doping. Int J Hydrog Energy 42(14):9333–9341
Sekine A, Seko N, Tamada M, Suzuki Y (2010) Biodegradable metal adsorbent synthesized by graft polymerization onto nonwoven cotton fabric. Radiat Phys Chem 79(1):16–21
Ma H, Morita K, Hoshina H, Seko N (2011) Synthesis of amine-type adsorbents with emulsion graft polymerization of 4-hydroxybutyl acrylate glycidylether. Mater Sci Appl 2(07):776
Nasef MM, Sugiarmawan IA (2010) Radiation induced emulsion grafting of glycidyl methacrylate onto high-density polyethylene: a kinetic study. Malays J Fundam Appl Sci 6(2):93–97
Taghizadeh MT, Khosravy M (2003) Kinetics and mechanism of graft copolymerization of vinyl monomers (acrylamide, acrylic acid, and methacrylate) onto starch by potassium dichromate as redox initiator. Iran Polym J 12(6):497–505
Singha AS, Rana AK (2011) Kinetics of graft copolymerization of acrylic acid ontocannabis indica fibre. Iran Polym J 11(137):913–929
Sun Y, Chmielewski AG (2017) Applications of ionizing radiation in materials processing. Institute of Nuclear Chemistry and Technology, Warszawa
Burillo G, Serrano-Gómez J, Bonifacio-Martínez J (2013) Adsorption of chromium (VI) on radiation grafted N, N-dimethylaminoethylmethacrylate onto polypropylene, from aqueous solutions. J Mex Chem Soc 57(2):80–84
Li J, He WD, Sc Han, Xl Sun, Ly Li, By Zhang (2009) Synthesis and micellization of PSt—PNIPAM—PDMAEMA hetero-arm star polymer with double thermo-responsibility. J Polym Sci Polym Chem 47(3):786–796
Meléndez-Ortiz HI, Varca GH, Lugão AB, Bucio E (2015) Smart polymers and coatings obtained by ionizing radiation: synthesis and biomedical applications. Open J Polym Chem 5(03):17
Ranogajec F (2009) Kinetic and structural factors in graft polymerization of styrene on polyolefins. Polimeri 29(4):217–227
Ugbolue SC (ed) (2017) The structural mechanics of polyolefin fibrous materials and nanocomposites. In: Polyolefin Fibres. Woodhead Publishing, pp 59–88
Kockler KB, Fleischhaker F, Barner-Kowollik C (2016) Free radical propagation rate coefficients of N-containing methacrylates: are we family? Macromolecules 49(22):8572–8580
Christodoulakis K, Vamvakaki M (2010) pH‐Responsive microgel particles comprising solely basic or acidic residues. In: Macromolecular Symposia, Wiley Online Library, no. 1, p 106–114
Bütün V, Armes S, Billingham N (2001) Synthesis and aqueous solution properties of near-monodisperse tertiary amine methacrylate homopolymers and diblock copolymers. Polymer 42(14):5993–6008
Ekberg C, Albinsson Y, Comarmond MJ, Brown PL (2000) Studies on the complexation behaviour of thorium (IV). 1. hydrolysis equilibria. J Solut Chem 29(1):63–86
Abd El-Magied MO, Elshehy EA, Manaa E-SA, Tolba AA, Atia AA (2016) Kinetics and thermodynamics studies on the recovery of thorium ions using amino resins with magnetic properties. Ind Eng Chem Res 55(43):11338–11345
Lai W, Zhang K, Shao P, Yang L, Ding L, Pavlostathis SG, Shi H, Zou L, Liang D, Luo X (2019) Optimization of adsorption configuration by DFT calculation for the design of adsorbent: a case study of palladium ion-imprinted polymers. J Hazard Mater 379:120791
Xiong J, Hu S, Liu Y, Yu J, Yu H, Xie L, Wen J, Wang X (2017) Polypropylene modified with amidoxime/carboxyl groups in separating uranium (VI) from thorium (IV) in aqueous solutions. ACS Sustain Chem Eng 5(2):1924–1930
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Financial support was provided by the Ministry of Environment, Science, Technology and Climate Change (MESTECC), Malaysia (FP0214D052(DSTIN)) and Japan Society for Promoting Science (JSPS), Japan under the RONPAKU program (R11703) granted to N.A.F. Othman.
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Othman, N.A.F., Selambakkannu, S., Yamanobe, T. et al. Radiation grafting of DMAEMA and DEAEMA-based adsorbents for thorium adsorption. J Radioanal Nucl Chem 324, 429–440 (2020). https://doi.org/10.1007/s10967-020-07078-9
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DOI: https://doi.org/10.1007/s10967-020-07078-9