Skip to main content
SpringerLink
Log in

Hydrophilic modification and cross-linking of polystyrene using the synthesized N,N′-(hexane-1,6-diyl)diacrylamide

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

The aim of this work was to synthesize a novel hydrophilic structure based on polystyrene (PS) cross-linked by using N,N′-(hexane-1,6-diyl)diacrylamide (HDBPA). FT-IR was carried out for chemical structure characterization of HDBPA and cross-linked samples. In addition to FT-IR, 1H NMR was also applied on HDBPA for more investigations. The results showed that HDBPA was synthetized through a condensation reaction, and consequently, it could successfully cross-link PS structure. Moreover, the determination of nitrogen content in HDBPA within PS network was investigated by means of elemental analysis. Afterward, the reactivity ratios between HDBPA and styrene were calculated via Fineman–Ross equation in which the obtained values were 0.66 and 0.23, respectively. On the other hand, by adding the HDBPA to PS the water contact angle was decreased from 73.6° to 57.4°, thereby proving the indispensable role of the cross-linking agent on hydrophilicity of the samples. Finally, the thermal behavior of the samples was studied using DSC and TGA analyses. According to DSC thermograms, there was a shift in Tg up to 30 °C for the samples with cross-linking densities ranging from 2.5 to 20 mol.%. In regard to the thermal stability of the cross-linked samples, the TGA curves revealed a reduction in this property owing to the presence of amide groups in HDBPA through the PS structure.

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.

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

Similar content being viewed by others

References

  1. Wang T, Zhu H, Xue H (2016) Reversible pH stimulus-response material based on amphiphilic block polymer self-assembly and its electrochemical application. Materials 9(6):478

    Article  Google Scholar 

  2. Sarmento B, Campana-Filho SP, Azevedo C, Almeida A, Silva D (2018) Synthesis and applications of amphiphilic chitosan derivatives for drug delivery applications. In: Neves AR, Reis S (eds) Nanoparticles in life sciences and biomedicine. Pan Stanford, New York, pp 45–73

    Google Scholar 

  3. Oh JY, Kim S, Baik HK, Jeong U (2016) Conducting polymer dough for deformable electronics. Adv Mater 28(22):4455–4461

    Article  CAS  Google Scholar 

  4. Zeynep EY, Antoine D, Brice C, Frank B, Christine J (2015) Double hydrophilic polyphosphoester containing copolymers as efficient templating agents for calcium carbonate microparticles. J Mater Chem B 3(36):7227–7236

    Article  CAS  Google Scholar 

  5. Gao H, Jones M-C, Chen J, Liang Y, Prud’homme RE, Leroux J-C (2008) Hydrophilic nanoreservoirs embedded into polymeric micro/nanoparticles: an approach to compatibilize polar molecules with hydrophobic matrixes. Chem Mater 20(13):4191–4193

    Article  CAS  Google Scholar 

  6. Ansary RH, Awang MB, Rahman MM (2014) Biodegradable poly (D, L-lactic-co-glycolic acid)-based micro/nanoparticles for sustained release of protein drugs-a review. Trop J Pharm Res 13(7):1179–1190

    Article  Google Scholar 

  7. Surmenev R, Chernozem R, Syromotina D, Oehr C, Baumbach T, Krause B, Boyandin A, Dvoinina L, Volova T, Surmeneva M (2019) Low-temperature argon and ammonia plasma treatment of poly-3-hydroxybutyrate films: surface topography and chemistry changes affect fibroblast cells in vitro. Eur Polym J 112:137–145

    Article  CAS  Google Scholar 

  8. Garcia-Ivars J, Wang-Xu X, Iborra-Clar M-I (2017) Application of post-consumer recycled high-impact polystyrene in the preparation of phase-inversion membranes for low-pressure membrane processes. Sep Purif Technol 175:340–351

    Article  CAS  Google Scholar 

  9. Ma Y, Dai J, Wu L, Fang G, Guo Z (2017) Enhanced anti-ultraviolet, anti-fouling and anti-bacterial polyelectrolyte membrane of polystyrene grafted with trimethyl quaternary ammonium salt modified lignin. Polymer 114:113–121

    Article  CAS  Google Scholar 

  10. Hannon JC, Kerry JP, Cruz-Romero M, Azlin-Hasim S, Morris M, Cummins E (2017) Kinetic desorption models for the release of nanosilver from an experimental nanosilver coating on polystyrene food packaging. Innov Food Sci Emerg Technol 44:149–158

    Article  CAS  Google Scholar 

  11. Okano T, Yamada N, Sakai H, Sakurai Y (1993) A novel recovery system for cultured cells using plasma-treated polystyrene dishes grafted with poly (N-isopropylacrylamide). J Biomed Mater Res 27(10):1243–1251

    Article  CAS  Google Scholar 

  12. Hwang S-J, Tseng M-C, Shu J-R, Yu HH (2008) Surface modification of cyclic olefin copolymer substrate by oxygen plasma treatment. Surf Coat Technol 202(15):3669–3674

    Article  CAS  Google Scholar 

  13. Qu J-B, Liu Y, Liu J-Y, Huan G-S, Wei S-N, Li S-H, Liu J-G (2018) One-pot synthesis of bimodal gigaporous polystyrene microspheres with hydrophilic surfaces. Macromolecules 51(11):4085–4093

    Article  CAS  Google Scholar 

  14. Fekete N, Béland AV, Campbell K, Clark SL, Hoesli CA (2018) Bags versus flasks: a comparison of cell culture systems for the production of dendritic cell–based immunotherapies. Transfusion 58(7):1800–1813

    Article  CAS  Google Scholar 

  15. Borisova O, Billon L, Zaremski M, Grassl B, Bakaeva Z, Lapp A, Stepanek P, Borisov O (2012) Synthesis and pH-and salinity-controlled self-assembly of novel amphiphilic block-gradient copolymers of styrene and acrylic acid. Soft Matter 8(29):7649–7659

    Article  CAS  Google Scholar 

  16. Oikonomou EK, Bethani A, Bokias G, Kallitsis JK (2011) Poly (sodium styrene sulfonate)-b-poly (methyl methacrylate) diblock copolymers through direct atom transfer radical polymerization: influence of hydrophilic–hydrophobic balance on self-organization in aqueous solution. Eur Polym J 47(4):752–761

    Article  CAS  Google Scholar 

  17. Luo T, Lin S, Xie R, Ju X-J, Liu Z, Wang W, Mou C-L, Zhao C, Chen Q, Chu L-Y (2014) pH-responsive poly (ether sulfone) composite membranes blended with amphiphilic polystyrene-block-poly (acrylic acid) copolymers. J Membr Sci 450:162–173

    Article  CAS  Google Scholar 

  18. Richard M-N, Bell M, Srinivasan R, Borhan A, Nagarajan R (2019) An approximate analytical approach to estimate the diffusivity of toxic chemicals in polymer barrier materials from the time evolution of sessile drop profiles. Polym Bull 76:339–364

    Article  Google Scholar 

  19. Sharmin E, Zafar F (eds) (2012) Polyurethane. In: Polyurethane an introduction. InTechOpen, London, pp 3–16

    Google Scholar 

  20. Modarresi-Saryazdi SM, Haddadi-Asl V, Salami-Kalajahi M (2018) N, N’-methylenebis (acrylamide)-crosslinked poly (acrylic acid) particles as doxorubicin carriers: a comparison between release behavior of physically loaded drug and conjugated drug via acid-labile hydrazone linkage. J Biomed Mater Res Part A 106(2):342–348

    Article  CAS  Google Scholar 

  21. Kong J, Yu S (2007) Fourier transform infrared spectroscopic analysis of protein secondary structures. Acta Biochim Biophys Sin 39(8):549–559

    Article  CAS  Google Scholar 

  22. Mu B, Shen R, Liu P (2009) Crosslinked polymeric nanocapsules from polymer brushes grafted silica nanoparticles via surface-initiated atom transfer radical polymerization. Colloids Surf B 74(2):511–515

    Article  CAS  Google Scholar 

  23. Ma Y, Jiang Y, Tan H, Zhang Y, Gu J (2017) A rapid and efficient route to preparation of isocyanate microcapsules. Polymers 9(7):274

    Article  Google Scholar 

  24. Yang H, Yan R, Chen H, Lee DH, Zheng C (2007) Characteristics of hemicellulose, cellulose and lignin pyrolysis. Fuel 86(12–13):1781–1788

    Article  CAS  Google Scholar 

  25. Abraham RJ, Griffiths L, Perez M (2013) 1H NMR spectra. Part 30: 1H chemical shifts in amides and the magnetic anisotropy, electric field and steric effects of the amide group. Magn Reson Chem 51(3):143–155

    Article  CAS  Google Scholar 

  26. Nikdel M, Salami-Kalajahi M, Hosseini MS (2014) Synthesis of poly (2-hydroxyethyl methacrylate-co-acrylic acid)-grafted graphene oxide nanosheets via reversible addition–fragmentation chain transfer polymerization. RSC Adv 4(32):16743–16750

    Article  CAS  Google Scholar 

  27. Yu L, Xu K, Ge L, Wan W, Darabi A, Xing M, Zhong W (2016) Cytocompatible, Photoreversible, and Self-Healing Hydrogels for Regulating Bone Marrow Stromal Cell Differentiation. Macromol Biosci 16(9):1381–1390

    Article  CAS  Google Scholar 

  28. Fineman M, Ross SD (1950) Linear method for determining monomer reactivity ratios in copolymerization. J Polym Sci 5(2):259–262

    Article  CAS  Google Scholar 

  29. Strobel M, Lyons C (2011) An essay on contact angle measurements. Plasma Process Polym 8(1):8–13

    Article  CAS  Google Scholar 

  30. Pal P, Singh S-K, Mishra S, Pandey J-P, Sen G (2019) Gum ghatti based hydrogel: microwave synthesis, characterization, 5-Fluorouracil encapsulation and ‘in vitro’drug release evaluation. Carbohydr Polym 222:114979

    Article  CAS  Google Scholar 

  31. Pal P, Pandey J, Sen G (2018) Sesbania gum based hydrogel as platform for sustained drug delivery: an ‘in vitro’study of 5-Fu release. Int J Biol Macromol 113:1116–1124

    Article  CAS  Google Scholar 

  32. Pal P, Pandey J-P, Sen G (2017) Modified PVP based hydrogel: synthesis, characterization and application in selective abstraction of metal ions from water. Mater Chem Phys 194:261–273

    Article  CAS  Google Scholar 

  33. Ueberreiter K, Kanig G (1950) Second-order transitions and mesh distribution functions of cross-linked polystyrenes. J Chem Phys 18(4):399–406

    Article  CAS  Google Scholar 

  34. Yamasaki R, Endo T (2013) Synthesis and polymerization of styrene monomer carrying isothiocyanate moiety and its copolymerization with HEMA based on chemo-selectivity to nucleophiles. J Polym Sci Part A Polym Chem 51(24):5215–5220

    Article  CAS  Google Scholar 

  35. Delman A, Stein A, Simms B (1967) Synthesis and thermal stability of structurally related aromatic Schiff bases and acid amides. J Macromol Sci Chem 1(1):147–178

    Article  CAS  Google Scholar 

  36. Wu HS, Chuang MH, Hwang JW (1999) Kinetics and thermal analysis of copolymerization of m-isopropenyl–α, α′-dimethylbenzyl isocyanate with styrene. J Appl Polym Sci 73(13):2763–2770

    Article  CAS  Google Scholar 

  37. Uhl FM, Levchik GF, Levchik SV, Dick C, Liggat JJ, Snape C, Wilkie CA (2001) The thermal stability of cross-linked polymers: methyl methacrylate with divinylbenzene and styrene with dimethacrylates. Polym Degrad Stab 71(2):317–325

    Article  CAS  Google Scholar 

  38. Hsieh W-h, Cheng W-t, Chen L-c, Lin S-y (2018) Non-isothermal dehydration kinetic study of aspartame hemihydrate using DSC, TGA and DSC-FTIR microspectroscopy. Asian J Pharm Sci 13(3):212–219

    Article  Google Scholar 

  39. Arrieta MP, López J, López D, Kenny J, Peponi L (2015) Development of flexible materials based on plasticized electrospun PLA–PHB blends: structural, thermal, mechanical and disintegration properties. Eur Polym J 73:433–446

    Article  CAS  Google Scholar 

Download references

Funding

The authors received no specific funding for this work.

Author information

Authors and Affiliations

  1. Department of Polymer Engineering and Color Technology, Amirkabir University of Technology, P.O. Box: 15875-4413, Tehran, Iran

    Seyedeh Mahnaz Modarresi-Saryazdi

  2. Department of Material Science and Engineering, Monash University, Melbourne, Australia

    Seyedeh Mahnaz Modarresi-Saryazdi

  3. Department of Chemical Engineering, Babol Noshirvani University of Technology, P.O. Box: 47148-71167, Babol, Iran

    Shahrzad Rahmani

  4. Nano-Biopolymers Research Laboratory, School of Chemical Engineering, College of Engineering, University of Tehran, P.O. Box: 11155-4563, Tehran, Iran

    Payam Zahedi

Authors
  1. Seyedeh Mahnaz Modarresi-Saryazdi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shahrzad Rahmani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Payam Zahedi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shahrzad Rahmani.

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

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Modarresi-Saryazdi, S.M., Rahmani, S. & Zahedi, P. Hydrophilic modification and cross-linking of polystyrene using the synthesized N,N′-(hexane-1,6-diyl)diacrylamide. Polym. Bull. 78, 1379–1391 (2021). https://doi.org/10.1007/s00289-020-03161-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-020-03161-z

Keywords

Search

Navigation