Abstract
Modified polymer surfaces have experienced rapid growth over the past decade in industries such as biomedical, bioprocessing, food packaging, microelectronics and textiles. Although the final use of the bio-functionalized polymer varies with each application, the general concept is the same. The first step is to design or select a polymer with bulk properties matching the needs of the final applications, such as conductivity, degradability, elasticity, optical clarity, origin (natural vs. synthetic) and strength. The second step is, therefore, to optimize surface functionalization techniques in order to introduce the desired type and amount of reactive functional groups. This chapter aims to introduce the advances in the covalent bonding to functionalized polymer surfaces, including the relevant techniques in the modification of the polymeric surface.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Alferiev, I. S., Connolly, J. M., Stachelek, S. J., Ottey, A., Rauova, L., & Levy, R. J. (2006). Surface heparinization of polyurethane via bromoalkylation of hard segment nitrogens. Biomacromolecules, 7(1), 317–322. https://doi.org/10.1021/bm0506694.
Aversa, T. M., da Silva, C. M. F., da Rocha, P. C. S., & Lucas, E. F. (2016). Influence of exchange group of modified glycidyl methacrylate polymer on phenol removal: A study by batch and continuous flow processes. Journal of Environmental Management, 182, 301–307. https://doi.org/10.1016/j.jenvman.2016.07.082.
Bahramian, B., Chrzanowski, W., Kondyurin, A., Thomas, N., & Dehghani, F. (2017). Fabrication of antimicrobial poly(propylene carbonate) film by plasma surface modification. Industrial & Engineering Chemistry Research, 56(44), 12578–12587. https://doi.org/10.1021/acs.iecr.7b01185.
Bastarrachea, L. J., & Goddard, J. M. (2013). Development of antimicrobial stainless steel via surface modification with N-halamines: Characterization of surface chemistry and N-halamine chlorination. Journal of Applied Polymer Science, 127(1), 821–831. https://doi.org/10.1002/app.37806.
Batmaz, R., Mohammed, N., Zaman, M., Minhas, G., Berry, R. M., & Tam, K. C. (2014). Cellulose nanocrystals as promising adsorbents for the removal of cationic dyes. Cellulose, 21(3), 1655–1665. https://doi.org/10.1007/s10570-014-0168-8.
Bayramoglu, G., Akbulut, A., & Arica, M. Y. (2015). Study of polyethyleneimine- and amidoxime-functionalized hybrid biomass of Spirulina (Arthrospira) platensis for adsorption of uranium (VI) ion. Environmental Science and Pollution Research, 22(22), 17998–18010. https://doi.org/10.1007/s11356-015-4990-9.
Bracone, M., Merino, D., González, J., Alvarez, V. A., & Gutiérrez, T. J. (2016). Chapter 6. Nanopackaging from natural fillers and biopolymers for the development of active and intelligent films. In S. Ikram & S. Ahmed (Eds.), Natural polymers: Derivatives, blends and composites (pp. 119–155). New York. EE.UU. ISBN: 978-1-63485-831-1: Editorial Nova Science.
Chaker, A., & Boufi, S. (2015). Cationic nanofibrillar cellulose with high antibacterial properties. Carbohydrate Polymers, 131, 224–232. https://doi.org/10.1016/j.carbpol.2015.06.003.
Chen, S. H., Fukazawa, K., Inoue, Y., & Ishihara, K. (2018). Photoinduced surface zwitterionization for antifouling of porous polymer substrates. Langmuir, 35(5), 1312–1319. https://doi.org/10.1021/acs.langmuir.8b01089.
Choi, S. W., Kim, W. S., & Kim, J. H. (2003). Surface modification of functional nanoparticles for controlled drug delivery. Journal of Dispersion Science and Technology, 24(3–4), 475–487. https://doi.org/10.1081/dis-120021803.
Cu, Y., & Saltzman, W. M. (2008). Controlled surface modification with poly(ethylene)glycol enhances diffusion of PLGA nanoparticles in human cervical mucus. Molecular Pharmaceutics, 6(1), 173–181. https://doi.org/10.1021/mp8001254.
Delfi, M., Ghomi, M., Zarrabi, A., Mohammadinejad, R., Taraghdari, Z. B., Ashrafizadeh, M., Zare, E. N., Agarwal, T., Padil, V. V. T., Mokhtari, B., Rossi, F., Perale, G., Sillanpaa, M., Borzacchiello, A., Maiti, T. K., & Makvandi, P. (2020). Functionalization of polymers and nanomaterials for biomedical applications: Antimicrobial platforms and drug carriers. Prosthesis, 2(2), 117–139. https://doi.org/10.3390/prosthesis2020012
De Bruycker, K., Delahaye, M., Cools, P., Winne, J., & Prez, F. E. D. (2017). Covalent fluorination strategies for the surface modification of polydienes. Macromolecular Rapid Communications, 38(11), 1700122. https://doi.org/10.1002/marc.201700122.
El-Saftawy, A. A., Ragheb, M. S., & Zakhary, S. G. (2018). Electron beam irradiation impact on surface structure and wettability of ethylene-vinyl alcohol copolymer. Radiation Physics and Chemistry, 147, 106–113. https://doi.org/10.1016/j.radphyschem.2018.02.001.
Fadida, T., Kroupitski, Y., Peiper, U. M., Bendikov, T., Sela, S., & Poverenov, E. (2014). Air-ozonolysis to generate contact active antimicrobial surfaces: Activation of polyethylene and polystyrene followed by covalent graft of quaternary ammonium salts. Colloids and Surfaces B: Biointerfaces, 122, 294–300. https://doi.org/10.1016/j.colsurfb.2014.07.003.
Fu, X., Shen, Y., Jiang, X., Huang, D., & Yan, Y. (2011). Chitosan derivatives with dual-antibacterial functional groups for antimicrobial finishing of cotton fabrics. Carbohydrate Polymers, 85(1), 221–227. https://doi.org/10.1016/j.carbpol.2011.02.019.
Gao, H., & Matyjaszewski, K. (2007). Synthesis of molecular brushes by “grafting onto” method: Combination of ATRP and click reactions. Journal of the American Chemical Society, 129(20), 6633–6639. https://doi.org/10.1021/ja0711617.
Gu, H., Ho, P. L., Tsang, K. W., Wang, L., & Xu, B. (2003). Using biofunctional magnetic nanoparticles to capture vancomycin-resistant enterococci and other Gram-positive bacteria at ultralow concentration. Journal of the American Chemical Society, 125(51), 15702–15703. https://doi.org/10.1021/ja0359310.
Gutiérrez, T. J., & Alvarez, V. A. (2017). Cellulosic materials as natural fillers in starch-containing matrix-based films: A review. Polymer Bulletin, 74(6), 2401–2430. https://doi.org/10.1007/s00289-016-1814-0.
Hasani, M., Cranston, E. D., Westman, G., & Gray, D. G. (2008). Cationic surface functionalization of cellulose nanocrystals. Soft Matter, 4(11), 2238–2244. https://doi.org/10.1039/b806789a.
He, X. M., Zhu, G. T., Zhu, Y. Y., Chen, X., Zhang, Z., Wang, S. T., Yuan, B. F., & Feng, Y. Q. (2014). Facile preparation of biocompatible sulfhydryl cotton fiber-based sorbents by “thiol-ene” click chemistry for biological analysis. ACS Applied Materials & Interfaces, 6(20), 17857–17864. https://doi.org/10.1021/am505876b.
He, X. M., Chen, X., Yuan, B. F., & Feng, Y. Q. (2017). Graft modification of cotton with phosphate group and its application to the enrichment of phosphopeptides. Journal of Chromatography A, 1484, 49–57. https://doi.org/10.1016/j.chroma.2017.01.020.
Herniou--Julien, C., Mendieta, J. R., & Gutiérrez, T. J. (2019). Characterization of biodegradable/non-compostable films made from cellulose acetate/corn starch blends processed under reactive extrusion conditions. Food Hydrocolloids, 89, 67–79. https://doi.org/10.1016/j.foodhyd.2018.10.024.
Hong, H. J., Lim, J. S., Hwang, J. Y., Kim, M., Jeong, H. S., & Park, M. S. (2018). Carboxymethlyated cellulose nanofibrils (CMCNFs) embedded in polyurethane foam as a modular adsorbent of heavy metal ions. Carbohydrate Polymers, 195, 136–142. https://doi.org/10.1016/j.carbpol.2018.04.081.
Jackson, J. K., Letchford, K., Wasserman, B. Z., Ye, L., Hamad, W. Y., & Burt, H. M. (2011). The use of nanocrystalline cellulose for the binding and controlled release of drugs. International Journal of Nanomedicine, 6, 321–330. https://doi.org/10.2147/ijn.s16749.
Jin, L., Li, W., Xu, Q., & Sun, Q. (2015). Amino-functionalized nanocrystalline cellulose as an adsorbent for anionic dyes. Cellulose, 22(4), 2443–2456. https://doi.org/10.1007/s10570-015-0649-4.
Kayaci, F., Aytac, Z., & Uyar, T. (2013). Surface modification of electrospun polyester nanofibers with cyclodextrin polymer for the removal of phenanthrene from aqueous solution. Journal of Hazardous Materials, 261, 286–294. https://doi.org/10.1016/j.jhazmat.2013.07.041.
Kim, Y. H., & Sun, G. (2001). Durable antimicrobial finishing of nylon fabrics with acid dyes and a quaternary ammonium salt. Textile Research Journal, 71(4), 318–323. https://doi.org/10.1177/004051750107100407.
Kim, Y. H., Choi, H. M., & Yoon, J. H. (1998). Synthesis of a quaternary ammonium derivative of chitosan and its application to a cotton antimicrobial finish. Textile Research Journal, 68(6), 428–434. https://doi.org/10.1177/004051759806800607.
Kobayashi, S., & Uyama, H. (2003). Biomacromolecules and bio-related macromolecules. Macromolecular Chemistry and Physics, 204(2), 235–256. https://doi.org/10.1002/macp.200290084.
Kwak, H. W., & Lee, K. H. (2018). Polyethylenimine-functionalized silk sericin beads for high-performance remediation of hexavalent chromium from aqueous solution. Chemosphere, 207, 507–516. https://doi.org/10.1016/j.chemosphere.2018.04.158.
Lee, M. Y., Yang, J. A., Jung, H. S., Beack, S., Choi, J. E., Hur, W., Koo, H., Kim, K., Yoon, S. K., & Hahn, S. K. (2012). Hyaluronic acid-gold nanoparticle/interferon α complex for targeted treatment of hepatitis C virus infection. ACS Nano, 6(11), 9522–9531. https://doi.org/10.1021/nn302538y.
Liu, C. Y., & Huang, C. J. (2016). Functionalization of polydopamine via the aza-michael reaction for antimicrobial interfaces. Langmuir, 32(19), 5019–5028. https://doi.org/10.1021/acs.langmuir.6b00990.
Makvandi, P., Ghaemy, M., Ghadiri, A. A., & Mohseni, M. (2015). Photocurable, antimicrobial quaternary ammonium-modified nanosilica. Journal of Dental Research, 94(10), 1401–1407. https://doi.org/10.1177/0022034515599973.
Makvandi, P., Ghaemy, M., & Mohseni, M. (2016). Synthesis and characterization of photo-curable bis-quaternary ammonium dimethacrylate with antimicrobial activity for dental restoration materials. European Polymer Journal, 74, 81–90. https://doi.org/10.1016/j.eurpolymj.2015.11.011.
Makvandi, P., Esposito Corcione, C., Paladini, F., Gallo, A. L., Montagna, F., Jamaledin, R., Pollini, M., & Maffezzoli, A. (2018a). Antimicrobial modified hydroxyapatite composite dental bite by stereolithography. Polymers for Advanced Technologies, 29(1), 364–371. https://doi.org/10.1002/pat.4123.
Makvandi, P., Jamaledin, R., Jabbari, M., Nikfarjam, N., & Borzacchiello, A. (2018b). Antibacterial quaternary ammonium compounds in dental materials: A systematic review. Dental Materials, 34(6), 851–867. https://doi.org/10.1016/j.dental.2018.03.014.
Makvandi, P., Ali, G. W., Della Sala, F., Abdel-Fattah, W. I., & Borzacchiello, A. (2019a). Biosynthesis and characterization of antibacterial thermosensitive hydrogels based on corn silk extract, hyaluronic acid and nanosilver for potential wound healing. Carbohydrate Polymers, 223, 115023. https://doi.org/10.1016/j.carbpol.2019.115023.
Makvandi, P., Ali, G. W., Della Sala, F., Abdel-Fattah, W. I., & Borzacchiello, A. (2019b). Hyaluronic acid/corn silk extract based injectable nanocomposite: A biomimetic antibacterial scaffold for bone tissue regeneration. Materials Science and Engineering: C, 107, 110195. https://doi.org/10.1016/j.msec.2019.110195.
Makvandi, P., Ting Gu, J., Zare, E. N., Ashtari, K., Moeini, A., Tay, F. R., & Niu, L.-N. (2019c). Polymeric and inorganic nanoscopical antimicrobial fillers in dentistry. Acta Biomaterialia, 101, 69–101. https://doi.org/10.1016/j.actbio.2019.09.025.
Mayol, L., Biondi, M., Russo, L., Malle, B. M., Schwach-Abdellaoui, K., & Borzacchiello, A. (2014). Amphiphilic hyaluronic acid derivatives toward the design of micelles for the sustained delivery of hydrophobic drugs. Carbohydrate Polymers, 102, 110–116. https://doi.org/10.1016/j.carbpol.2013.11.003.
Monier, M., & Abdel-Latif, D. A. (2013). Modification and characterization of PET fibers for fast removal of Hg(II), Cu(II) and Co(II) metal ions from aqueous solutions. Journal of Hazardous Materials, 250, 122–130. https://doi.org/10.1016/j.jhazmat.2013.01.056.
Nafee, N., Taetz, S., Schneider, M., Schaefer, U. F., & Lehr, C. M. (2007). Chitosan-coated PLGA nanoparticles for DNA/RNA delivery: Effect of the formulation parameters on complexation and transfection of antisense oligonucleotides. Nanomedicine: Nanotechnology, Biology and Medicine, 3(3), 173–183. https://doi.org/10.1016/j.nano.2007.03.006.
Park, J., Fong, P. M., Lu, J., Russell, K. S., Booth, C. J., Saltzman, W. M., & Fahmy, T. M. (2009). PEGylated PLGA nanoparticles for the improved delivery of doxorubicin. Nanomedicine: Nanotechnology, Biology and Medicine, 5(4), 410–418. https://doi.org/10.1016/j.nano.2009.02.002.
Pearson, H. A., & Urban, M. W. (2014). Simple click reactions on polymer surfaces leading to antimicrobial behavior. Journal of Materials Chemistry B, 2(15), 2084–2087. https://doi.org/10.1039/c3tb21865a.
Pei, A., Butchosa, N., Berglund, L. A., & Zhou, Q. (2013). Surface quaternized cellulose nanofibrils with high water absorbency and adsorption capacity for anionic dyes. Soft Matter, 9(6), 2047–2055. https://doi.org/10.1039/c2sm27344f.
Pour, Z. S., Makvandi, P., & Ghaemy, M. (2015). Performance properties and antibacterial activity of crosslinked films of quaternary ammonium modified starch and poly(vinyl alcohol). International Journal of Biological Macromolecules, 80, 596–604. https://doi.org/10.1016/j.ijbiomac.2015.07.008.
Qiao, H., Zhou, Y., Yu, F., Wang, E., Min, Y., Huang, Q., Pang, L., & Ma, T. (2015). Effective removal of cationic dyes using carboxylate-functionalized cellulose nanocrystals. Chemosphere, 141, 297–303. https://doi.org/10.1016/j.chemosphere.2015.07.078.
Ram, B., & Chauhan, G. S. (2018). New spherical nanocellulose and thiol-based adsorbent for rapid and selective removal of mercuric ions. Chemical Engineering Journal, 331, 587–596. https://doi.org/10.1016/j.cej.2017.08.128.
Richey, T., Iwata, H., Oowaki, H., Uchida, E., Matsuda, S., & Ikada, Y. (2000). Surface modification of polyethylene balloon catheters for local drug delivery. Biomaterials, 21(10), 1057–1065. https://doi.org/10.1016/s0142-9612(99)00281-1.
Selkälä, T., Suopajärvi, T., Sirviö, J. A., Luukkonen, T., Lorite, G. S., Kalliola, S., Sillanpää, M., & Liimatainen, H. (2018). Rapid uptake of pharmaceutical salbutamol from aqueous solutions with anionic cellulose nanofibrils: The importance of pH and colloidal stability in the interaction with ionizable pollutants. Chemical Engineering Journal, 350, 378–385. https://doi.org/10.1016/j.cej.2018.05.163.
Sheikhi, A., Safari, S., Yang, H., & van de Ven, T. G. (2015). Copper removal using electrosterically stabilized nanocrystalline cellulose. ACS Applied Materials & Interfaces, 7(21), 11301–11308. https://doi.org/10.1021/acsami.5b01619.
Sirviö, J. A., Hasa, T., Leiviskä, T., Liimatainen, H., & Hormi, O. (2016). Bisphosphonate nanocellulose in the removal of vanadium (V) from water. Cellulose, 23(1), 689–697. https://doi.org/10.1007/s10570-015-0819-4.
Srivastava, S., Kardam, A., & Raj, K. R. (2012). Nanotech reinforcement onto cellulosic fibers: Green remediation of toxic metals. International Journal of Green Nanotechnology, 4(1), 46–53. https://doi.org/10.1080/19430892.2012.654744.
Sumerlin, B. S., Tsarevsky, N. V., Louche, G., Lee, R. Y., & Matyjaszewski, K. (2005). Highly efficient “click” functionalization of poly (3-azidopropyl methacrylate) prepared by ATRP. Macromolecules, 38(18), 7540–7545. https://doi.org/10.1021/ma0511245.
Sun, G., Xu, X., Bickett, J. R., & Williams, J. F. (2001). Durable and regenerable antibacterial finishing of fabrics with a new hydantoin derivative. Industrial & Engineering Chemistry Research, 40(4), 1016–1021. https://doi.org/10.1021/ie000657t.
Tountas, M., Georgiadou, D. G., Zeniou, A., Seintis, K., Soultati, A., Polydorou, E., Gardelis, S., Douvas, A. M., Speliotis, T., Tsikritzis, D., Kennou, S., Fakis, M., Gogolides, E., Tsoukalas, D., Argitis, P., & Vasilopoulou, M. (2018). Plasma induced degradation and surface electronic structure modification of poly(3-hexylthiophene) films. Polymer Degradation and Stability, 149, 162–172. https://doi.org/10.1016/j.polymdegradstab.2017.12.010.
Tripathi, B. P., Dubey, N. C., & Stamm, M. (2013). Functional polyelectrolyte multilayer membranes for water purification applications. Journal of Hazardous Materials, 252, 401–412. https://doi.org/10.1016/j.jhazmat.2013.02.052.
Tsarevsky, N. V., Bencherif, S. A., & Matyjaszewski, K. (2007). Graft copolymers by a combination of ATRP and two different consecutive click reactions. Macromolecules, 40(13), 4439–4445. https://doi.org/10.1021/ma070705m.
Van Camp, W., Germonpré, V., Mespouille, L., Dubois, P., Goethals, E. J., & Du Prez, F. E. (2007). New poly (acrylic acid) containing segmented copolymer structures by combination of “click” chemistry and atom transfer radical polymerization. Reactive and Functional Polymers, 67(11), 1168–1180. https://doi.org/10.1016/j.reactfunctpolym.2007.07.004.
Wang, D. (2019). A critical review of cellulose-based nanomaterials for water purification in industrial processes. Cellulose, 26(2), 687–701. https://doi.org/10.1007/s10570-018-2143-2.
Yang, J. S., Xie, Y. J., & He, W. (2011). Research progress on chemical modification of alginate: A review. Carbohydrate Polymers, 84(1), 33–39. https://doi.org/10.1016/j.carbpol.2010.11.048.
Yang, H., Alam, M. N., & van de Ven, T. G. (2013). Highly charged nanocrystalline cellulose and dicarboxylated cellulose from periodate and chlorite oxidized cellulose fibers. Cellulose, 20(4), 1865–1875. https://doi.org/10.1007/s10570-013-9966-7.
Ye, S., Jiang, L., Wu, J., Su, C., Huang, C., Liu, X., & Shao, W. (2018). Flexible amoxicillin-grafted bacterial cellulose sponges for wound dressing: In vitro and in vivo evaluation. ACS Applied Materials & Interfaces, 10(6), 5862–5870. https://doi.org/10.1021/acsami.7b16680.
Yu, X., Tong, S., Ge, M., Wu, L., Zuo, J., Cao, C., & Song, W. (2013). Adsorption of heavy metal ions from aqueous solution by carboxylated cellulose nanocrystals. Journal of Environmental Sciences, 25(5), 933–943. https://doi.org/10.1016/S1001-0742(12)60145-4.
Zare, E. N., Makvandi, P., Ashtari, B., Rossi, F., Motahari, A., & Perale, G. (2019a). Progress in conductive polyaniline-based nanocomposites for biomedical applications: A review. Journal of Medicinal Chemistry, 63, 1–22. https://doi.org/10.1021/acs.jmedchem.9b00803.
Zare, E. N., Makvandi, P., & Tay, F. R. (2019b). Recent progress in the industrial and biomedical applications of tragacanth gum. Carbohydrate Polymers, 212, 450–467. https://doi.org/10.1016/j.carbpol.2019.02.076.
Zarrintaj, P., Jouyandeh, M., Ganjali, M. R., Hadavand, B. S., Mozafari, M., Sheiko, S. S., Vatankhah-Varnoosfaderani, M., Gutiérrez, T. J., & Saeb, M. R. (2019). Thermo-sensitive polymers in medicine: A review. European Polymer Journal, 117, 402–423. https://doi.org/10.1016/j.eurpolymj.2019.05.024.
Zhan, J., Wang, L., Zhu, Y., Gao, H., Chen, Y., Chen, J., Jia, Y., He, J., Fang, Z., Zhu, Y., Mao, C., Ren, L., & Wang, Y. (2018). Temperature-controlled reversible exposure and hiding of antimicrobial peptides on an implant for killing bacteria at room temperature and improving biocompatibility in vivo. ACS Applied Materials & Interfaces, 10(42), 35830–35837. https://doi.org/10.1021/acsami.8b14534.
Zhang, X., Zhao, J., Cheng, L., Lu, C., Wang, Y., He, X., & Zhang, W. (2014). Acrylic acid grafted and acrylic acid/sodium humate grafted bamboo cellulose nanofibers for Cu2+ adsorption. RSC Advances, 4(98), 55195–55201. https://doi.org/10.1039/c4ra08307e.
Acknowledgments
Does not declare.
Conflicts of Interest The authors declare no conflict of interest.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2020 The Editor(s) (if applicable) and The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Ghanooni, S., Nikfarjam, N., Makvandi, P. (2020). Surface Reactive and Active Polymers. In: Gutiérrez, T.J. (eds) Reactive and Functional Polymers Volume Four. Springer, Cham. https://doi.org/10.1007/978-3-030-52052-6_3
Download citation
DOI: https://doi.org/10.1007/978-3-030-52052-6_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-52051-9
Online ISBN: 978-3-030-52052-6
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)