Skip to main content
SpringerLink
Log in

Enhanced amination and adsorption performance of functional copolymer synthesized via RAFT-mediated radiation grafting in emulsion

  • ORIGINAL PAPER
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Grafted polymer substrates bearing diglycol amic acid (DA) ligands for Eu and Sm adsorption were prepared using a two-step post-grafting modification of polyethylene/polypropylene-g-poly(glycidyl methacrylate) (PE/PP-g-PGMA) that was synthesized through reversible addition-fragmentation chain transfer (RAFT)-mediated γ-radiation induced graft polymerization in emulsion phase. The PE/PP-g-PGMA prepared with RAFT mediation exhibited better reactivity towards amination reaction at 40 °C than the graft copolymers prepared without RAFT mediation, with the epoxide to amino group conversion of the former exceeding the latter by as much as 20%. The DA ligands were incorporated to the aminated graft copolymer by subsequent reaction with diglycolic anhydride to yield the DA-modified PE/PP-g-PGMA adsorbent. The effects of pH and competing ions on the uptake of Eu and Sm have been investigated. The DA-modified PE/PP-g-PGMA prepared with RAFT mediation showed higher Eu and Sm adsorption percentage than the DA adsorbent that was synthesized without RAFT mediation. The DA-modified PE/PP-g-PGMA exhibited higher affinity for Eu over Cu and Fe in acidic solutions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Haque N, Hughes A, Lim S, Vernon C (2014) Rare Earth Elements: Overview of Mining, Mineralogy, Uses, Sustainability and Environmental Impact. Resources 3:614–635

    Article  Google Scholar 

  2. Fernandez V (2017) Rare-earth elements market: A historical and financial perspective. Resour Policy 53:26–45

    Article  Google Scholar 

  3. Kubota F, Goto M, Nakashio F (1993) Extraction of rare earth metals with 2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester in the presence of diethylenetriaminepentaacetic acid in aqueous phase. Solvent Extr Ion Exch 11:437–453

    Article  CAS  Google Scholar 

  4. Lee GS, Uchikoshi M, Mimura K, Isshiki M (2010) Separation of major impurities Ce, Pr, Nd, Sm, Al, Ca, Fe, and Zn from La using bis(2-ethylhexyl)phosphoric acid (D2EHPA)-impregnated resin in a hydrochloric acid medium. Sep Purif Technol 71:186–191

    Article  CAS  Google Scholar 

  5. Innocenzi V, Vegliò FJ (2012) Recovery of rare earths and base metals from spent nickel-metal hydride batteries by sequential sulphuric acid leaching and selective precipitations. Power Sour 211:184–191

    Article  CAS  Google Scholar 

  6. Baba Y, Fukami A, Kubota F, Kamiya N, Goto M (2014) Selective extraction of scandium from yttrium and lanthanides with amic acid-type extractant containing alkylamide and glycine moieties. RSC Adv 4:50726–50730

    Article  CAS  Google Scholar 

  7. Hosomomi Y, Wakabayashi R, Kubota F, Kamiya N, Goto M (2016) Diglycolic amic acid-modified E. coli as a biosorbent for the recovery of rare earth elements. Biochem Eng J 113:102–106

    Article  CAS  Google Scholar 

  8. Barsbay M, Kavakli PA, Tilki S, Kavakli C, Guven O (2018) Porous cellulosic adsorbent for the removal of Cd (II), Pb(II) and Cu(II) ions from aqueous media. Radiat Phys Chem 142:70–76

    Article  CAS  Google Scholar 

  9. Madrid JF, Ueki Y, Abad LV, Yamanobe T, Seko N (2017) RAFT-mediated graft polymerization of glycidyl methacrylate in emulsion from polyethylene/polypropylene initiated with γ-radiation. J Appl Polym Sci 134:45270

    Article  CAS  Google Scholar 

  10. Przybytniak G, Kornacka E, Fuks L (2011) Functionalization of polyamide surface by radiation-induced grafting of N-vinyl-pyrrolidone and acrylamide. J Polym Res 18:541–547

    Article  CAS  Google Scholar 

  11. Madrid J, Ueki Y, Seko N (2013) Abaca/polyester nonwoven fabric functionalization for metal ion adsorbent synthesis via electron beam-induced emulsion grafting. Radiat Phys Chem 90:104–110

    Article  CAS  Google Scholar 

  12. Li S, Wei J (2012) Radiation synthesis of polypropylene-acrylate grafted fiber and its remediation in the spillage of water-insoluble organic chemicals. J Polym Res 19:9841

    Article  CAS  Google Scholar 

  13. Ueki Y, Seko N, Hoshina H, Tamada M (2007) Preparation of Polylactic Acid Nonwoven Fabric-based Metal Adsorbent by Radiation-induced Graft Polymerization. J Ion Exch 18:214–219

    Article  CAS  Google Scholar 

  14. Seko N, Katakai A, Tamada M, Sugo T, Yoshii F (2004) Fine Fibrous Amidoxime Adsorbent Synthesized by Grafting and Uranium Adsorption–Elution Cyclic Test with Seawater. Sep Sci Technol 39:3753–3767

    Article  CAS  Google Scholar 

  15. Barsbay M, Güven O (2013) RAFT mediated grafting of poly(acrylic acid) (PAA) from polyethylene/polypropylene (PE/PP) nonwoven fabric via preirradiation. Polymer 54:4838–4848

    Article  CAS  Google Scholar 

  16. Akbulut M, Barsbay M, Guven O (2018). Radiat Phys Chem 142:77–81

    Article  CAS  Google Scholar 

  17. Celik G, Barsbay M, Guven O (2016) Towards new proton exchange membrane materials with enhanced performance via RAFT polymerization. Polym Chem 7:701–714

    Article  CAS  Google Scholar 

  18. Kodama Y, Barsbay M, Güven O (2014) Radiation-induced and RAFT-mediated grafting of poly(hydroxyethyl methacrylate) (PHEMA) from cellulose surfaces. Radiat Phys Chem 94:98–104

    Article  CAS  Google Scholar 

  19. Barsbay M, Guven O (2009) A short review of radiation-induced raft-mediated graft copolymerization: A powerful combination for modifying the surface properties of polymers in a controlled manner. Radiat Phys Chem 78:1054–1059

    Article  CAS  Google Scholar 

  20. Madrid JF, Abad LV, Yamanobe T, Seko N (2017) Effects of chain transfer agent on the electron beam-induced graft polymerization of glycidyl methacrylate in emulsion phase. Colloid Polym Sci 295:1007–1016

    Article  CAS  Google Scholar 

  21. Barsbay M, Guven O, Bessbousse H, Wade TL, Beuneu F, Clochard M-C (2013) Nanopore size tuning of polymeric membranes using the RAFT-mediated radical polymerization. J Membrane Sci 445:135–145

    Article  CAS  Google Scholar 

  22. Barsbay M, Guven O (2014) Grafting in confined spaces: Functionalization of nanochannels of track-etched membranes. Radiat Phys Chem 105:26–30

    Article  CAS  Google Scholar 

  23. Ogata T, Narita H, Tanaka M (2014) Immobilization of Diglycol Amic Acid on Silica Gel for Selective Recovery of Rare Earth Elements. Chem Lett 43:1414–1416

    Article  CAS  Google Scholar 

  24. Barsbay M, Güven O, Stenzel MH, Davis TP, Barner-Kowollik C, Barner L (2007) Verification of Controlled Grafting of Styrene from Cellulose via Radiation-Induced RAFT Polymerization. Macromolecules 40:7140–7147

    Article  CAS  Google Scholar 

  25. Barbey R, Laporte V, Alnabulsi S, Klok HA (2013) Postpolymerization Modification of Poly(glycidyl methacrylate) Brushes: An XPS Depth-Profiling Study. Macromolecules 46:6151–6158

    Article  CAS  Google Scholar 

  26. Celik SU, Bozkurt A (2008) Preparation and proton conductivity of acid-doped 5-aminotetrazole functional poly(glycidyl methacrylate). Eur Polym J 44:213–218

    Article  CAS  Google Scholar 

  27. Solangi IB, Bhatti AA, Qazi MA, Memon S, Bhanger MI (2012). Pak J Anal Environ Chem 13:129–136

    CAS  Google Scholar 

  28. Ogata T, Narita H, Tanaka M, Hoshino M, Kon Y, Watanabe Y (2016) Selective recovery of heavy rare earth elements from apatite with an adsorbent bearing immobilized tridentate amido ligands. Sep Purif Technol 159:157–160

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge: Japan Society for the Promotion of Science (JSPS) for the RONPAKU (JSPS) fellowship awarded to J.F. Madrid; Philippine Council for Industry, Energy and Emerging Technology Research and Development, Department of Science and Technology (PCIEERD, DOST) for the financial support extended to J.F. Madrid; and Dr. Atsumi Miyashita (Research Project Positron Nanoscience, QST) for the XPS measurements.

Author information

Authors and Affiliations

  1. Department of Science and Technology, Philippine Nuclear Research Institute, Diliman, 1101, Quezon City, Philippines

    Jordan F. Madrid & Lucille V. Abad

  2. Division of Molecular Science, Gunma University, Kiryu, Gunma, 376-8515, Japan

    Jordan F. Madrid & Takeshi Yamanobe

  3. Research Project Environmental Polymer, Quantum Beam Science Directorate, National Institutes for Quantum and Radiological Science and Technology, Watanuki-machi, Takasaki City, Gunma, 370-1292, Japan

    Yuji Ueki & Noriaki Seko

Authors
  1. Jordan F. Madrid
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuji Ueki
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lucille V. Abad
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Takeshi Yamanobe
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Noriaki Seko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jordan F. Madrid.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Madrid, J.F., Ueki, Y., Abad, L.V. et al. Enhanced amination and adsorption performance of functional copolymer synthesized via RAFT-mediated radiation grafting in emulsion. J Polym Res 25, 193 (2018). https://doi.org/10.1007/s10965-018-1585-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-018-1585-4

Keywords

Search

Navigation