Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

Development of a superabsorbent polymer using iodine transfer polymerization

Abstract

We succeeded in developing a novel class of acrylic acid (AA)-based superabsorbent polymers (SAPs) with remarkably improved absorption performance by applying iodine transfer polymerization (ITP). A specific organoiodine chain transfer agent was newly developed and found to provide moderate to good control over the polymerization of AA in aqueous solution. Dynamic light scattering (DLS) measurements revealed that the polymer network prepared using our ITP technology is relatively homogeneous. Our new SAP exhibits a good balance between absorption capacity and gel strength, and it enables a quick response to diversified customer needs in the diaper industry. To the best of our knowledge, this work is the first case in which reversible-deactivation radical polymerization (RDRP) has been practically applied to commodity polymer products. This review focuses on how we connected the old but highly practical ITP and SAP production.

Access options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

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

References

  1. 1.

    Buchholzs, FL, Graham, AT, editors Modern superabsorbent polymer technology. New York: Wiley-VCH; 1998.

  2. 2.

    Tatemoto M, Suzuki T, Tomoda M, Furukawa Y, Ueta Y. Fluorine-containing polymer easily curable and its curable composition. JP S53-125491A. Japan: Daikin Kogyo Co., Ltd; 1978.

  3. 3.

    Oka M, Tatemoto M. Vinylidene fluoride-hexafluoropropylene copolymer having terminal iodines. Contemp Top Polym Sci. 1984;4:763–77.

    CAS  Article  Google Scholar 

  4. 4.

    Tatemoto M. Development of “iodine transfer polymerization” and its applications to telechelically reactive polymers. Kobunshi Ronbunshu. 1992;49:765–83.

    CAS  Article  Google Scholar 

  5. 5.

    David G, Boyer C, Tonnar J, Ameduri B, Lacroix-Desmazes P, Boutevin P. Use of iodocompounds in radical polymerization. Chem Rev. 2006;106:3936–62.

    CAS  Article  Google Scholar 

  6. 6.

    Ni Y, Zhang L, Cheng Z, Zhu X. Iodine-mediated reversible-deactivation radical polymerization: a powerful strategy for polymer synthesis. Polym Chem. 2009;10:2504–15.

    Article  Google Scholar 

  7. 7.

    Flory, PJ. Principles of polymer chemistry. Ithaca: Cornell University Press; 1953. p.589.

  8. 8.

    Shibayama M. Spatial inhomogeneity and dynamic fluctuations of polymer gels. Macromol Chem Phys. 1998;199:1–30.

    CAS  Article  Google Scholar 

  9. 9.

    Lorenzo FD, Seiffert S. Nanostructural heterogeneity in polymer networks and gels. Polym Chem. 2015;6:5515–28.

    Article  Google Scholar 

  10. 10.

    Seiffert S. Origin of nanostructural inhomogeneity in polymer-network gels. Polym Chem. 2017;8:4472–87.

    CAS  Article  Google Scholar 

  11. 11.

    Matyjaszewski K, Müller AHE, editors Controlled and living polymerizations. Wiley-VCH Verlag GmbH & Co. KGaA; 2010.

  12. 12.

    Jenkins AD, Jones RG, Moad G. Terminology for reversible deactivation radical polymerization previously called “controlled” radical or “living” radical polymerization. Pure Appl Chem. 2009;82:483–91.

    Article  Google Scholar 

  13. 13.

    Norisuye T, Morinaga T, Tran-Cong-Miyata Q, Goto A, Fukuda T, Shibayama M. Comparison of the gelation dynamics for polystyrenes prepared by conventional and living radical polymerization: a time-resolved dynamic light scattering study. Polymer. 2005;46:1982–94.

    CAS  Article  Google Scholar 

  14. 14.

    Gao H, Matyjaszewski K. Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels. Prog Polym Sci. 2009;34:317–50.

    CAS  Article  Google Scholar 

  15. 15.

    Voit B. New polymers: Beautiful structures, but how can we bring them to the market? Angew Chem Int Ed. 2017;56:2810–1.

    CAS  Article  Google Scholar 

  16. 16.

    Georges MK, Veregin RPN, Kazmaier PM, Hamer GK. Narrow molecular weight resins by a free-radical polymerization process. Macromolecules. 1993;26:2987–8.

    CAS  Article  Google Scholar 

  17. 17.

    Wang J-S, Matyjaszewski K. Controlled/“living” radical polymerization. Atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc. 1995;117:5614–5.

    CAS  Article  Google Scholar 

  18. 18.

    Kato M, Kamigaito M, Sawamoto M, Higashimura T. Polymerization of methyl methacrylate with the carbon tetrachloride/dichlorotris-(triphenylphosphine)ruthenium (II)/methylaluminum bis(2,6-di-tert-butylphenoxide) initiating system: Possibility of living radical polymerization. Macromolecules. 1995;28:1721–3.

    CAS  Article  Google Scholar 

  19. 19.

    Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, Mayadunne RTA, Meijs GF, Moad CL, Moad G, Rizzardo E, Thang SH. Living free-radical polymerization by reversible addition-fragmentation chain transfer: the RAFT process. Macromolecules. 1998;31:5559–62.

    CAS  Article  Google Scholar 

  20. 20.

    Yamago S, Iida K, Yoshida J. Organotellurium compounds as novel initiators for controlled/living radical polymerizations. Synthesis of functionalized polystyrenes and end-group modifications. J Am Chem Soc. 2002;124:2874–5.

    CAS  Article  Google Scholar 

  21. 21.

    Lei L, Tanishima M, Goto A, Kaji H, Yamaguchi Y, Komatsu H, Jitsukawa T, Miyamoto M. Systematic study on alkyl iodide initiators in living radical polymerization with organic catalysts. Macromolecules. 2014;47:6610–8.

    CAS  Article  Google Scholar 

  22. 22.

    Matsubara Y, Miyajima T. Water-absorbent resin particles and method for producing same. WO2017-57706A1, Japan: SDP Global Co., Ltd; 2017.

  23. 23.

    Shibayama M, Norisuye T, Nomura S. Cross-link density dependence of spatial inhomogeneities and dynamic fluctuations of poly(N-isopropylacrylamide) gels. Macromolecules. 1996;29:8746–50.

    CAS  Article  Google Scholar 

  24. 24.

    Tanishima M, Goto A, Lei L, Ohtsuki A, Kaji H, Nomura A, Tsujii Y, Yamaguchi Y, Komatsu H, Miyamoto M. Macromolecular architectures designed by living radical polymerization with organic catalysts. Polymers. 2014;6:311–26.

    Article  Google Scholar 

  25. 25.

    Destarac M. Industrial development of reversible-deactivation radical polymerization: is induction period over? Polym Chem. 2018;9:4947–67.

    CAS  Article  Google Scholar 

  26. 26.

    Destarac M. Controlled radical polymerization: Industrial stakes, obstacles and achievements. Macromol React Eng. 2010;4:165–79.

    CAS  Article  Google Scholar 

Download references

Acknowledgements

The authors would like to thank Prof. A. Goto from Nanyang Technological University for helpful discussions and insightful suggestions.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Toru Miyajima.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Miyajima, T., Matsubara, Y., Komatsu, H. et al. Development of a superabsorbent polymer using iodine transfer polymerization. Polym J 52, 365–373 (2020). https://doi.org/10.1038/s41428-019-0292-2

Download citation

Further reading

Search

Quick links