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Synthesis and structural characterization of lignin/silica hybrid nanoparticles functionalized with sulfonic acid-terminated polyamidoamine

Abstract

Lignin nanoparticles (LNPs) with an average diameter (\(\overline{d}_{n}\)) of 78.2 nm were prepared via rapid pH decrease of alkaline solution to acidic state. Two lignin/silica hybrid (LSH) nanoparticles, i.e., LSH1 (\(\overline{d}_{n}\) = 80.9 nm) and LSH2 (\(\overline{d}_{n}\) = 83.0 nm), with different lignin contents were synthesized using LNP via sol–gel method and then aminated using 3-aminopropyltriethoxysilane. Polyamidoamine (PAMAM) was then grafted onto the aminated LSHs, resulting in LSHx-PAMAM G1.0 (x = 1 or 2). Firstly, methyl acrylate was reacted with aminated LSHs. Then, methyl ester groups in the 0.5th generation were reacted with ethylenediamine (EDA), resulting in the LSHx-PAMAM G1.0. Structure and functional groups of the bio-based nanoparticles were characterized quantitatively using adequate techniques. In addition, LSH1-PAMAM G1.0 was kept for a long time in EDA (pH 13), so that the physically bonded LNP was dissolved and S-PAMAM G1.0 was obtained. LSH1-PAMAM G1.0 and S-PAMAM G1.0 were sulfonated using 1,3-propanesultone and a high degree of sulfonation, i.e., 99.93% and 99.34%, respectively, was obtained.

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References

  1. Abdollahi M, Habashi RB, Mohsenpour M (2019) Poly(ε-caprolactone) chains grafted from lignin, hydroxymethylated lignin and silica/lignin hybrid macroinitiators: synthesis and characterization of lignin-based thermoplastic copolymers. Ind Crop Prod 130:547–557

  2. Alvarez A, Guzman C, Rivas S (2014) Composites membranes based on Nafion and PAMAM dendrimers for PEMFC applications. Int J Hydrog Energy 39:16686–16693

  3. Bayrami Habashi R (2016) Modification of lignin with formaldehyde and silica nanoparticle in order to investigate its reactivity in the condensation polymer synthesis. Tarbiat Modares University

  4. Chu F, Lin B, Qiu B et al (2012) Polybenzimidazole/zwitterion-coated silica nanoparticle hybrid proton conducting membranes for anhydrous proton exchange membrane application. J Mater Chem 22:18411–18417

  5. Duan S, Kouketsu T, Kazama S, Yamada K (2006) Development of PAMAM dendrimer composite membranes for CO2 separation. J Membr Sci 283:2–6

  6. Duncan R (2003) The dawning era of polymer therapeutics. Nat Rev Drug Discov 2:347

  7. Dykes GM (2001) Dendrimers: a review of their appeal and applications. J Chem Technol Biotechnol 76:903–918. https://doi.org/10.1002/jctb.464

  8. Esfand R, Tomalia DA (2001) Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discov Today 6:427–436

  9. Evstigneyev EI, Shevchenko SM (2019) Structure, chemical reactivity and solubility of lignin: a fresh look. Wood Sci Technol 53:7–47

  10. Frangville C, Rutkevičius M, Richter AP, Velev OD, Stoyanov SD, Paunov VN (2012) Fabrication of environmentally biodegradable lignin nanoparticles. ChemPhysChem 13:4235–4243

  11. Gerrans K, Luhrs A, Feider C, Margerum LD (2016) Silica nanoparticles functionalized with polyamidoamine (PAMAM) dendrimers as platforms for photoluminescence (PL) sensing of copper and cyanide ions. J Colloid Interface Sci 470:276–283

  12. Gu Z, Ding J, Yuan N (2013) Polybenzimidazole/zwitterion-coated polyamidoamine dendrimer composite membranes for direct methanol fuel cell applications. Int J Hydrog Energy 38:16410–16417

  13. Habashi RB, Abdollahi M (2018) Functional groups and structural characterization of unmodified and functionalized lignin by titration, elemental analysis, HNMR and FTIR techniques. Iran J Polymer Sci Technol 30:405–418

  14. Hayashi J, Shoji T, Watada Y, Muroyama K (1997) Preparation of silica–lignin Xerogel. Langmuir 13:4185–4186

  15. Kaneko Y, Imai Y, Shirai K, Yamauchi T, Tsubokawa N (2006) Preparation and properties of hyperbranched poly(amidoamine) grafted onto a colloidal silica surface. Colloid Surfaces A 289:212–218

  16. Klapiszewski Ł, Nowacka M, Milczarek GTJ (2013) Physicochemical and electrokinetic properties of silica/lignin biocomposites. Carbohydr Polym 94:345–355

  17. Kojima C, Kono K, Maruyama K, Takagishi T (2000) Synthesis of polyamidoamine dendrimers having poly (ethylene glycol) grafts and their ability to encapsulate anticancer drugs. Bioconjug Chem 11:910–917

  18. Kouketsu T, Duan S, Kai T, Kazama S, Yamada K (2007) PAMAM dendrimer composite membrane for CO2 separation: formation of a chitosan gutter layer. J Membr Sci 287:51–59

  19. Kumar R, Kumar K, Bhowmik S (2018) Mechanical characterization and quantification of tensile, fracture and viscoelastic characteristics of wood filler reinforced epoxy composite. Wood Sci Technol 52:677–699

  20. Lee J, Shin H, Rhee H, Kim Y, Song M, Kim M (2006) Composite electrolyte membrane with nanoscopic dendrimers and method of preparing same. US Patent 2006116479,

  21. Liu X, Ma D, Tang H et al (2014) Polyamidoamine dendrimer and oleic acid-functionalized graphene as biocompatible and efficient gene delivery vectors. ACS Appl Matet Intefaces 6:8173–8183

  22. Liyanage AD, Ferraris JP, Musselman IH, Yang D-J, Andersson TE, Son DY Jr, Balkus KJ (2012) Nafion-sulfonated dendrimer composite membranes for fuel cell applications. J Membr Sci 392:175–180

  23. Mishra SB, Mishra AK, Krause RW, Mamba BB (2009) Growth of silicon carbide nanorods from the hybrid of lignin and polysiloxane using sol-gel process and polymer blend technique. Mater Lett 63:2449–2451

  24. Nowacka M, Klapiszewski Ł, Norman M, Jesionowski T (2013) Dispersive evaluation and surface chemistry of advanced, multifunctional silica/lignin hybrid biomaterials. Cent Eur J Chem 11:1860–1873

  25. Okazaki M, Murota M, Kawaguchi Y, Tsubokawa N (2001) Curing of epoxy resin by ultrafine silica modified by grafting of hyperbranched polyamidoamine using dendrimer synthesis methodology. J Appl Polym Sci 80:573–579

  26. Pourmahdi M, Abdollahi M, Nasiri A (2018) Synthesis and characterization of native lignin/acrylamide-based copolymers obtained by graft radical polymerization. Iran J Polym Sci Technol (Persian) 30:501–516. https://doi.org/10.22063/jipst.2018.1533

  27. Pu W-F, Liu R, Wang K-Y, Li K-X, Yan Z-P, Li B, Zhao L (2015) Water-soluble core–shell hyperbranched polymers for enhanced oil recovery. Ind Eng Chem Res 54:798–807

  28. Qu Y, Tian Y, Zou B et al (2010) A novel mesoporous lignin/silica hybrid from rice husk produced by a sol–gel method. Bioresour Technol 101:8402–8405

  29. Rui Z, Xifu X, Qilong T, Hua H, Jian Y, Yuan H (2012) Preparation of lignin–silica hybrids and its application in intumescent flame-retardant poly (lactic acid) system. High Perform Polym 24:738–746

  30. Telysheva G, Dizhbite T, Evtuguin D et al (2009) Design of siliceous lignins—novel organic/inorganic hybrid sorbent materials. Scr Mater 60:687–690

  31. Tomalia DA, Uppuluri S, Swanson DR, Li J (2000) Dendrimers as reactive modules for the synthesis of new structure-controlled, higher-complexity megamers. Pure Appl Chem 72:2343–2358

  32. Wang B, Sun Y, Davis TP, Ke PC, Wu Y, Ding F (2018) Understanding effects of PAMAM dendrimer size and surface chemistry on serum protein binding with discrete molecular dynamics simulations. ACS Sustain Chem Eng 6:11704–11715

  33. Wu Y, Chen C, Zhou Q et al (2019) Polyamidoamine dendrimer decorated nanoparticles as an adsorbent for magnetic solid-phase extraction of tetrabromobisphenol A and 4-nonylphenol from environmental water samples. J Colloid Interface Sci 539:361–369

  34. Zhu J, Xue L, Wei W, Mu C, Jiang M, Zhou Z (2015) Modification of lignin with silane coupling agent to improve the interface of poly(l-lactic) acid/lignin composites. BioResources 10:4315–4325

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Acknowledgements

The author, M. Abdollahi, would like to acknowledge the Tarbiat Modares University (Grant Number # 57935) for the financial support.

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Correspondence to Mahdi Abdollahi.

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Ahmadi, H., Abdollahi, M. Synthesis and structural characterization of lignin/silica hybrid nanoparticles functionalized with sulfonic acid-terminated polyamidoamine. Wood Sci Technol 54, 249–268 (2020). https://doi.org/10.1007/s00226-019-01153-5

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