Abstract
On the basis of the world’s continuing consumption of raw materials, there was an urgent need to seek sustainable resources. Lignin, the second naturally abundant biomass, accounts for 15–35% of the cell walls of terrestrial plants and is considered waste for low-cost applications such as thermal and electricity generation. The impressive characteristics of lignin, such as its high abundance, low density, biodegradability, antioxidation, antibacterial capability, and its CO2 neutrality and enhancement, render it an ideal candidate for developing new polymer/composite materials. In past decades, considerable works have been conducted to effectively utilize waste lignin as a component in polymer matrices for the production of high-performance lignin-based polymers. This chapter is intended to provide an overview of the recent advances and challenges involving lignin-based polymers utilizing lignin macromonomer and its derived monolignols. These lignin-based polymers include phenol resins, polyurethane resins, polyester resins, epoxy resins, etc. The structural characteristics and functions of lignin-based polymers are discussed in each section. In addition, we also try to divide various lignin reinforced polymer composites into different polymer matrices, which can be separated into thermoplastics, rubber, and thermosets composites. This chapter is expected to increase the interest of researchers worldwide in lignin-based polymers and develop new ideas in this field.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Ragauskas, AJ, Beckham, GT, Biddy, MJ, Chandra, R, Chen, F, Davis, MF, et al.. Lignin valorization: improving lignin processing in the biorefinery. Science 2014;344:1246843. https://doi.org/10.1126/science.1246843.Search in Google Scholar PubMed
2. Luterbacher, JS, Azarpira, A, Motagamwala, AH, Lu, F, Ralph, J, Dumesic, JA. Lignin monomer production integrated into the γ-valerolactone sugar platform. Energy Environ Sci 2015;8:2657–63. https://doi.org/10.1039/c5ee01322d.Search in Google Scholar
3. Shuai, L, Amiri, MT, Questell-Santiago, YM, Heroguel, F, Li, YD, Kim, H, et al.. Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization. Science 2016;354:329–33. https://doi.org/10.1126/science.aaf7810.Search in Google Scholar PubMed
4. Upton, BM, Kasko, AM. Strategies for the conversion of lignin to high-value polymeric materials: review and perspective. Chem Rev 2016;116:2275–306. https://doi.org/10.1021/acs.chemrev.5b00345.Search in Google Scholar PubMed
5. Li, C, Zhao, X, Wang, A, Huber, GW, Zhang, T. Catalytic transformation of lignin for the production of chemicals and fuels. Chem Rev 2015;115:11559–624. https://doi.org/10.1021/acs.chemrev.5b00155.Search in Google Scholar PubMed
6. Sun, Z, Fridrich, B, de Santi, A, Elangovan, S, Barta, K. Bright side of lignin depolymerization: toward new platform chemicals. Chem Rev 2018;118:614–78. https://doi.org/10.1021/acs.chemrev.7b00588.Search in Google Scholar PubMed PubMed Central
7. Kai, D, Tan, MJ, Chee, PL, Chua, YK, Yap, YL, Loh, XJ. Towards lignin-based functional materials in a sustainable world. Green Chem 2016;18:1175–200. https://doi.org/10.1039/c5gc02616d.Search in Google Scholar
8. Gioia, C, Lo Re, G, Lawoko, M, Berglund, L. Tunable thermosetting epoxies based on fractionated and well-characterized lignins. J Am Chem Soc 2018;140:4054–61. https://doi.org/10.1021/jacs.7b13620.Search in Google Scholar PubMed
9. Liu, H, Chung, H. Lignin-based polymers via graft copolymerization. J Polym Sci Polym Chem 2017;55:3515–28. https://doi.org/10.1002/pola.28744.Search in Google Scholar
10. Doherty, WO, Mousavioun, P, Fellows, CM. Value-adding to cellulosic ethanol: lignin polymers. Ind Crop Prod 2011;33:259–76. https://doi.org/10.1016/j.indcrop.2010.10.022.Search in Google Scholar
11. Zakzeski, J, Bruijnincx, PCA, Jongerius, AL, Weckhuysen, BM. The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 2010;110:3552–99. https://doi.org/10.1021/cr900354u.Search in Google Scholar PubMed
12. Gordobil, O, Robles, E, Egüés, I, Labidi, J. Lignin-ester derivatives as novel thermoplastic materials. RSC Adv 2016;6:86909–17. https://doi.org/10.1039/c6ra20238a.Search in Google Scholar
13. Sen, S, Patil, S, Argyropoulos, DS. Thermal properties of lignin in copolymers, blends, and composites: a review. Green Chem 2015;17:4862–87. https://doi.org/10.1039/c5gc01066g.Search in Google Scholar
14. Thakur, VK, Thakur, MK, Raghavan, P, Kessler, MR. Progress in green polymer composites from lignin for multifunctional applications: a review. ACS Sustain Chem Eng 2014;2:1072–92. https://doi.org/10.1021/sc500087z.Search in Google Scholar
15. Thakur, VK, Thakur, MK. Recent advances in green hydrogels from lignin: a review. Int J Biol Macromol 2015;72:834–47. https://doi.org/10.1016/j.ijbiomac.2014.09.044.Search in Google Scholar PubMed
16. Liu, W-J, Jiang, H, Yu, H-Q. Thermochemical conversion of lignin to functional materials: a review and future directions. Green Chem 2015;17:4888–907. https://doi.org/10.1039/c5gc01054c.Search in Google Scholar
17. Zhao, S, Abu-Omar, MM. Materials based on technical bulk lignin. ACS Sustain Chem Eng 2021;9:1477–93. https://doi.org/10.1021/acssuschemeng.0c08882.Search in Google Scholar
18. Vishtal, AG, Kraslawski, A. Challenges in industrial applications of technical lignins. BioResources 2011;6:3547–68. https://doi.org/10.15376/biores.6.3.3547-3568.Search in Google Scholar
19. Duval, A, Lawoko, M. A review on lignin-based polymeric, micro-and nano-structured materials. React Funct Polym 2014;85:78–96. https://doi.org/10.1016/j.reactfunctpolym.2014.09.017.Search in Google Scholar
20. Sternberg, J, Sequerth, O, Pilla, S. Green chemistry design in polymers derived from lignin: review and perspective. Prog Polym Sci 2021;113:101344. https://doi.org/10.1016/j.progpolymsci.2020.101344.Search in Google Scholar
21. Balakshin, MY, Capanema, EA, Sulaeva, I, Schlee, P, Huang, Z, Feng, M, et al.. New opportunities in the valorization of technical lignins. ChemSusChem 2021;14:1016–36. https://doi.org/10.1002/cssc.202002553.Search in Google Scholar PubMed
22. Calvo-Flores, FG, Dobado, JA. Lignin as renewable raw material. ChemSusChem 2010;3:1227–35. https://doi.org/10.1002/cssc.201000157.Search in Google Scholar PubMed
23. Hu, J, Zhang, Q, Lee, D-J. Kraft lignin biorefinery: a perspective. Bioresour Technol 2018;247:1181–3. https://doi.org/10.1016/j.biortech.2017.08.169.Search in Google Scholar PubMed
24. Gellerstedt, G. Softwood Kraft lignin: raw material for the future. Ind Crop Prod 2015;77:845–54. https://doi.org/10.1016/j.indcrop.2015.09.040.Search in Google Scholar
25. Crestini, C, Lange, H, Sette, M, Argyropoulos, DS. On the structure of softwood Kraft lignin. Green Chem 2017;19:4104–21. https://doi.org/10.1039/c7gc01812f.Search in Google Scholar
26. Gratzl, JS, Chen, C-L. Chemistry of pulping: lignin reactions. Washington, DC, USA: ACS Publications; 2000.10.1021/bk-2000-0742.ch020Search in Google Scholar
27. Deshpande, R, Giummarella, N, Henriksson, G, Germgård, U, Sundvall, L, Grundberg, H, et al.. The reactivity of lignin carbohydrate complex (LCC) during manufacture of dissolving sulfite pulp from softwood. Ind Crop Prod 2018;115:315–22. https://doi.org/10.1016/j.indcrop.2018.02.038.Search in Google Scholar
28. Aro, T, Fatehi, P. Production and application of lignosulfonates and sulfonated lignin. ChemSusChem 2017;10:1861–77. https://doi.org/10.1002/cssc.201700082.Search in Google Scholar PubMed
29. Fatehi, P, Chen, J. Extraction of technical lignins from pulping spent liquors, challenges and opportunities, Production of biofuels and chemicals from lignin. Heidelberg, Germany: Springer; 2016:35–54 pp.10.1007/978-981-10-1965-4_2Search in Google Scholar
30. El Hage, R, Brosse, N, Sannigrahi, P, Ragauskas, A. Effects of process severity on the chemical structure of Miscanthus ethanol organosolv lignin. Polym Degrad Stabil 2010;95:997–1003. https://doi.org/10.1016/j.polymdegradstab.2010.03.012.Search in Google Scholar
31. Konnerth, H, Zhang, J, Ma, D, Prechtl, MH, Yan, N. Base promoted hydrogenolysis of lignin model compounds and organosolv lignin over metal catalysts in water. Chem Eng Sci 2015;123:155–63. https://doi.org/10.1016/j.ces.2014.10.045.Search in Google Scholar
32. El Hage, R, Brosse, N, Chrusciel, L, Sanchez, C, Sannigrahi, P, Ragauskas, A. Characterization of milled wood lignin and ethanol organosolv lignin from miscanthus. Polym Degrad Stabil 2009;94:1632–8. https://doi.org/10.1016/j.polymdegradstab.2009.07.007.Search in Google Scholar
33. Lou, R, Wu, S-B. Products properties from fast pyrolysis of enzymatic/mild acidolysis lignin. Appl Energy 2011;88:316–22. https://doi.org/10.1016/j.apenergy.2010.06.028.Search in Google Scholar
34. Lei, M, Wu, S, Liang, J, Liu, C. Comprehensive understanding the chemical structure evolution and crucial intermediate radical in situ observation in enzymatic hydrolysis/mild acidolysis lignin pyrolysis. J Anal Appl Pyrol 2019;138:249–60. https://doi.org/10.1016/j.jaap.2019.01.004.Search in Google Scholar
35. Schubert, WJ, Nord, F. Investigations on lignin and lignification. II. The characterization of enzymatically liberated lignin. J Am Chem Soc 1950;72:3835–8. https://doi.org/10.1021/ja01165a001.Search in Google Scholar
36. Schubert, W, Passannante, A, Stevens, GD, Bier, M, Nord, F. Investigations on lignin and lignification. XIII. Electrophoresis of native and enzymatically liberated Lignins 1. J Am Chem Soc 1953;75:1869–73. https://doi.org/10.1021/ja01104a027.Search in Google Scholar
37. Jiang, B, Yao, Y, Liang, Z, Gao, J, Chen, G, Xia, Q, et al.. Lignin-based direct ink printed structural scaffolds. Small 2020;16:e1907212. https://doi.org/10.1002/smll.201907212.Search in Google Scholar PubMed
38. Ren, T, Qi, W, Su, R, He, Z. Promising techniques for depolymerization of lignin into value-added chemicals. ChemCatChem 2019;11:639–54. https://doi.org/10.1002/cctc.201801428.Search in Google Scholar
39. Laurichesse, S, Avérous, L. Chemical modification of lignins: towards biobased polymers. Prog Polym Sci 2014;39:1266–90. https://doi.org/10.1016/j.progpolymsci.2013.11.004.Search in Google Scholar
40. del Río, JC, Rencoret, J, Gutiérrez, A, Elder, T, Kim, H, Ralph, J. Lignin monomers from beyond the canonical monolignol biosynthetic pathway: another brick in the wall. ACS Sustain Chem Eng 2020;8:4997–5012. https://doi.org/10.1021/acssuschemeng.0c01109.Search in Google Scholar
41. Thornburg, NE, Pecha, MB, Brandner, DG, Reed, ML, Vermaas, JV, Michener, WE, et al.. Mesoscale reaction–diffusion phenomena governing lignin-first biomass fractionation. ChemSusChem 2020;13:4495–509. https://doi.org/10.1002/cssc.202000558.Search in Google Scholar PubMed
42. Liu, X, Bouxin, FP, Fan, J, Budarin, VL, Hu, C, Clark, JH. Recent advances in the catalytic depolymerization of lignin towards phenolic chemicals: a review. ChemSusChem 2020;13:4296. https://doi.org/10.1002/cssc.202001213.Search in Google Scholar PubMed PubMed Central
43. Da Cunha, C, Deffieux, A, Fontanille, M. Synthesis and polymerization of lignin-based macromonomers. III. Radical copolymerization of lignin-based macromonomers with methyl methacrylate. J Appl Polym Sci 1993;48:819–31. https://doi.org/10.1002/app.1993.070480507.Search in Google Scholar
44. Azhar, SS, Ahn, DJ. Purification of monomers leads to high-quality lignin macromonomers. Bristol, England: IOP Conference Series: Materials Science and Engineering, IOP Publishing; 2019:012021 p.10.1088/1757-899X/548/1/012021Search in Google Scholar
45. Petrović, ZS. Polyurethanes from vegetable oils. Polym Rev 2008;48:109–55. https://doi.org/10.1080/15583720701834224.Search in Google Scholar
46. Sen, S, Martin, JD, Argyropoulos, DS. Review of cellulose non-derivatizing solvent interactions with emphasis on activity in inorganic molten salt hydrates. ACS Sustain Chem Eng 2013;1:858–70. https://doi.org/10.1021/sc400085a.Search in Google Scholar
47. Aniceto, JP, Portugal, I, Silva, CM. Biomass-based polyols through oxypropylation reaction. ChemSusChem 2012;5:1358–68. https://doi.org/10.1002/cssc.201200032.Search in Google Scholar PubMed
48. Lin, S, Huang, J, Chang, PR, Wei, S, Xu, Y, Zhang, Q. Structure and mechanical properties of new biomass-based nanocomposite: castor oil-based polyurethane reinforced with acetylated cellulose nanocrystal. Carbohydr Polym 2013;95:91–9. https://doi.org/10.1016/j.carbpol.2013.02.023.Search in Google Scholar PubMed
49. Nam, G-Y, Oh, J-S, Park, I-K, Luong, ND, Yoon, H-K, Lee, S-H, et al.. High molecular-weight thermoplastic polymerization of Kraft lignin macromers with diisocyanate. BioResources 2014;9:2359–71.10.15376/biores.9.2.2359-2371Search in Google Scholar
50. Hu, TQ. Chemical modification, properties, and usage of lignin. New York, USA: Springer; 2002.10.1007/978-1-4615-0643-0Search in Google Scholar
51. Xue, B-L, Wen, J-L, Sun, R-C. Lignin-based rigid polyurethane foam reinforced with pulp fiber: synthesis and characterization. ACS Sustain Chem Eng 2014;2:1474–80. https://doi.org/10.1021/sc5001226.Search in Google Scholar
52. Pohjanlehto, H, Setälä, HM, Kiely, DE, McDonald, AG. Lignin-xylaric acid-polyurethane-based polymer network systems: preparation and characterization. J Appl Polym Sci 2014;131:1–7. https://doi.org/10.1002/app.39714.Search in Google Scholar
53. Yiamsawas, D, Baier, G, Thines, E, Landfester, K, Wurm, FR. Biodegradable lignin nanocontainers. RSC Adv 2014;4:11661–3. https://doi.org/10.1039/c3ra47971d.Search in Google Scholar
54. Zhang, Y, Liao, J, Fang, X, Bai, F, Qiao, K, Wang, L. Renewable high-performance polyurethane bioplastics derived from lignin–poly(ε-caprolactone). ACS Sustain Chem Eng 2017;5:4276–84. https://doi.org/10.1021/acssuschemeng.7b00288.Search in Google Scholar
55. Mavila, S, Sinha, J, Hu, Y, Podgórski, M, Shah, PK, Bowman, CN. High refractive index photopolymers by Thiol–Yne “click” polymerization. ACS Appl Mater Interfaces 2021;13:15647–58. https://doi.org/10.1021/acsami.1c00831.Search in Google Scholar PubMed
56. Yilmaz, G, Yagci, Y. Light-induced step-growth polymerization. Prog Polym Sci 2020;100:101178. https://doi.org/10.1016/j.progpolymsci.2019.101178.Search in Google Scholar
57. Cao, Y, Liu, Z, Zheng, B, Ou, R, Fan, Q, Li, L, et al.. Synthesis of lignin-based polyols via thiol-ene chemistry for high-performance polyurethane anticorrosive coating. Compos B Eng 2020;200:108295. https://doi.org/10.1016/j.compositesb.2020.108295.Search in Google Scholar
58. Braun, E, Levin, BC. Polyesters: a review of the literature on products of combustion and toxicity. Fire Mater 1986;10:107–23. https://doi.org/10.1002/fam.810100304.Search in Google Scholar
59. Guo, Z-X, Gandini, A. Polyesters from lignin—2. The copolyesterification of Kraft lignin and polyethylene glycols with dicarboxylic acid chlorides. Eur Polym J 1991;27:1177–80. https://doi.org/10.1016/0014-3057(91)90053-q.Search in Google Scholar
60. Thanh Binh, NT, Luong, ND, Kim, DO, Lee, SH, Kim, BJ, Lee, YS, et al.. Synthesis of lignin-based thermoplastic copolyester using Kraft lignin as a macromonomer. Compos Interface 2009;16:923–35. https://doi.org/10.1163/092764409x12477479344485.Search in Google Scholar
61. Bonini, C, D’Auria, M, Emanuele, L, Ferri, R, Pucciariello, R, Sabia, AR. Polyurethanes and polyesters from lignin. J Appl Polym Sci 2005;98:1451–6. https://doi.org/10.1002/app.22277.Search in Google Scholar
62. Malkappa, K, Jana, T. Simultaneous improvement of tensile strength and elongation: an unprecedented observation in the case of hydroxyl terminated polybutadiene polyurethanes. Ind Eng Chem Res 2013;52:12887–96. https://doi.org/10.1021/ie401923e.Search in Google Scholar
63. Sivasankarapillai, G, McDonald, AG. Synthesis and properties of lignin-highly branched poly (ester-amine) polymeric systems, Biomass Bioenergy 2011;35:919–31. https://doi.org/10.1016/j.biombioe.2010.11.002.Search in Google Scholar
64. Scarica, C, Suriano, R, Levi, M, Turri, S, Griffini, G. Lignin functionalized with succinic anhydride as building block for biobased thermosetting polyester coatings. ACS Sustain Chem Eng 2018;6:3392–401. https://doi.org/10.1021/acssuschemeng.7b03583.Search in Google Scholar
65. Fan, Q, Liu, T, Zhang, C, Liu, Z, Zheng, W, Ou, R, et al.. Extraordinary solution-processability of lignin in phenol–maleic anhydride and dielectric films with controllable properties. J Mater Chem A 2019;7:23162–72. https://doi.org/10.1039/C9TA06665A.Search in Google Scholar
66. Jiang, B, Chen, C, Liang, Z, He, S, Kuang, Y, Song, J, et al.. Lignin as a wood-inspired binder enabled strong, water stable, and biodegradable paper for plastic replacement. Adv Funct Mater 2019;30:1906307. https://doi.org/10.1002/adfm.201906307.Search in Google Scholar
67. Cao, D, Zhang, Q, Hafez, AM, Jiao, Y, Ma, Y, Li, H, et al.. Lignin-derived holey, layered, and thermally conductive 3D scaffold for lithium dendrite suppression. Small Methods 2019;3:1800539. https://doi.org/10.1002/smtd.201800539.Search in Google Scholar
68. Kai, D, Zhang, K, Jiang, L, Wong, HZ, Li, Z, Zhang, Z, et al.. Sustainable and antioxidant lignin–polyester copolymers and nanofibers for potential healthcare applications. ACS Sustain Chem Eng 2017;5:6016–25. https://doi.org/10.1021/acssuschemeng.7b00850.Search in Google Scholar
69. Auvergne, R, Caillol, S, David, G, Boutevin, B, Pascault, J-P. Biobased thermosetting epoxy: present and future. Chem Rev 2014;114:1082–115. https://doi.org/10.1021/cr3001274.Search in Google Scholar PubMed
70. Qin, J, Woloctt, M, Zhang, J. Use of polycarboxylic acid derived from partially depolymerized lignin as a curing agent for epoxy application. ACS Sustain Chem Eng 2013;2:188–93. https://doi.org/10.1021/sc400227v.Search in Google Scholar
71. Zhao, S, Abu-Omar, MM. Synthesis of renewable thermoset polymers through successive lignin modification using lignin-derived phenols. ACS Sustain Chem Eng 2017;5:5059–66. https://doi.org/10.1021/acssuschemeng.7b00440.Search in Google Scholar
72. Nonaka, Y, Tomita, B, Hatano, Y. Synthesis of lignin/epoxy resins in aqueous systems and their properties. Holzforschung 1997;51:183–7. https://doi.org/10.1515/hfsg.1997.51.2.183.Search in Google Scholar
73. Engelmann, G, Ganster, J. Bio-based epoxy resins with low molecular weight Kraft lignin and pyrogallol. Holzforschung 2014;68:435–46. https://doi.org/10.1515/hf-2013-0023.Search in Google Scholar
74. Zhao, S, Huang, X, Whelton, AJ, Abu-Omar, MM. Formaldehyde-free method for incorporating lignin into epoxy thermosets. ACS Sustain Chem Eng 2018;6:10628–36. https://doi.org/10.1021/acssuschemeng.8b01962.Search in Google Scholar
75. Feldman, D, Banu, D, Khoury, M. Epoxy–lignin polyblends. III. Thermal properties and infrared analysis. J Appl Polym Sci 1989;37:877–87. https://doi.org/10.1002/app.1989.070370403.Search in Google Scholar
76. Feldman, D, Banu, D, Natansohn, A, Wang, J. Structure–properties relations of thermally cured epoxy–lignin polyblends. J Appl Polym Sci 1991;42:1537–50. https://doi.org/10.1002/app.1991.070420607.Search in Google Scholar
77. Wang, J, Banu, D, Feldman, D. Epoxy–lignin polyblends: effects of various components on adhesive properties. J Adhes Sci Technol 1992;6:587–98. https://doi.org/10.1163/156856192x00412.Search in Google Scholar
78. Wang, G, Liu, X, Zhang, J, Sui, W, Jang, J, Si, C. One-pot lignin depolymerization and activation by solid acid catalytic phenolation for lightweight phenolic foam preparation. Ind Crop Prod 2018;124:216–25. https://doi.org/10.1016/j.indcrop.2018.07.080.Search in Google Scholar
79. Nair, CR. Advances in addition-cure phenolic resins. Prog Polym Sci 2004;29:401–98. https://doi.org/10.1016/j.progpolymsci.2004.01.004.Search in Google Scholar
80. Gardziella, A, Pilato, LA, Knop, A. Phenolic resins: chemistry, applications, standardization, safety and ecology. Des Moines, Iowa, USA: Springer Science & Business Media; 2013.Search in Google Scholar
81. Alonso, M, Oliet, M, Garcia, J, Rodriguez, F, Echeverría, J. Gelation and isoconversional kinetic analysis of lignin–phenol–formaldehyde resol resins cure. Chem Eng J 2006;122:159–66. https://doi.org/10.1016/j.cej.2006.06.008.Search in Google Scholar
82. Vazquez, G, Antorrena, G, González, J, Mayor, J. Lignin-phenol-formaldehyde adhesives for exterior grade plywoods. Bioresour Technol 1995;51:187–92. https://doi.org/10.1016/0960-8524(94)00120-p.Search in Google Scholar
83. Danielson, B, Simonson, R. Kraft lignin in phenol formaldehyde resin. Part 1. Partial replacement of phenol by Kraft lignin in phenol formaldehyde adhesives for plywood. J Adhes Sci Technol 1998;12:923–39. https://doi.org/10.1163/156856198x00542.Search in Google Scholar
84. Danielson, B, Simonson, R. Kraft lignin in phenol formaldehyde resin. Part 2. Evaluation of an industrial trial. J Adhes Sci Technol 1998;12:941–6. https://doi.org/10.1163/156856198x00551.Search in Google Scholar
85. Podschun, J, Saake, B, Lehnen, R. Reactivity enhancement of organosolv lignin by phenolation for improved bio-based thermosets. Eur Polym J 2015;67:1–11. https://doi.org/10.1016/j.eurpolymj.2015.03.029.Search in Google Scholar
86. Cederholm, L, Xu, Y, Tagami, A, Sevastyanova, O, Odelius, K, Hakkarainen, M. Microwave processing of lignin in green solvents: a high-yield process to narrow-dispersity oligomers. Ind Crop Prod 2020;145:112152. https://doi.org/10.1016/j.indcrop.2020.112152.Search in Google Scholar
87. Zhu, G, Jin, D, Zhao, L, Ouyang, X, Chen, C, Qiu, X. Microwave-assisted selective cleavage of C C bond for lignin depolymerization. Fuel Process Technol 2017;161:155–61. https://doi.org/10.1016/j.fuproc.2017.03.020.Search in Google Scholar
88. Gao, C, Li, M, Zhu, C, Hu, Y, Shen, T, Li, M, et al.. One-pot depolymerization, demethylation and phenolation of lignin catalyzed by HBr under microwave irradiation for phenolic foam preparation. Compos B Eng 2021;205:108530. https://doi.org/10.1016/j.compositesb.2020.108530.Search in Google Scholar
89. Boerjan, W, Ralph, J, Baucher, M. Lignin biosynthesis. Annu Rev Plant Biol 2003;54:519–46. https://doi.org/10.1146/annurev.arplant.54.031902.134938.Search in Google Scholar PubMed
90. Fache, M, Boutevin, B, Caillol, S. Vanillin production from lignin and its use as a renewable chemical. ACS Sustain Chem Eng 2015;4:35–46. https://doi.org/10.1021/acssuschemeng.5b01344.Search in Google Scholar
91. Fache, M, Boutevin, B, Caillol, S. Epoxy thermosets from model mixtures of the lignin-to-vanillin process. Green Chem 2016;18:712–25. https://doi.org/10.1039/c5gc01070e.Search in Google Scholar
92. Holmberg, AL, Stanzione, JF, Wool, RP, Epps, TH. A facile method for generating designer block copolymers from functionalized lignin model compounds. ACS Sustain Chem Eng 2014;2:569–73. https://doi.org/10.1021/sc400497a.Search in Google Scholar
93. Wang, S, Ma, S, Xu, C, Liu, Y, Dai, J, Wang, Z, et al.. Vanillin-derived high-performance flame retardant epoxy resins. Facile Synth Propert Macromol 2017;50:1892–901. https://doi.org/10.1021/acs.macromol.7b00097.Search in Google Scholar
94. Van, A, Chiou, K, Ishida, H. Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring. Polymer 2014;55:1443–51. https://doi.org/10.1016/j.polymer.2014.01.041.Search in Google Scholar
95. Wang, S, Ma, S, Li, Q, Yuan, W, Wang, B, Zhu, J. Robust, fire-safe, monomer-recovery, highly malleable thermosets from renewable bioresources. Macromolecules 2018;51:8001–12. https://doi.org/10.1021/acs.macromol.8b01601.Search in Google Scholar
96. Liu, T, Hao, C, Zhang, S, Yang, X, Wang, L, Han, J, et al.. A self-healable high glass transition temperature bioepoxy material based on vitrimer chemistry. Macromolecules 2018;51:5577–85. https://doi.org/10.1021/acs.macromol.8b01010.Search in Google Scholar
97. Mu, L, Shi, Y, Chen, L, Ji, T, Yuan, R, Wang, H, et al.. [N-Methyl-2-pyrrolidone][C1-C4 carboxylic acid]: a novel solvent system with exceptional lignin solubility. Chem Commun (Camb) 2015;51:13554–7. https://doi.org/10.1039/c5cc04191k.Search in Google Scholar PubMed
98. Fan, Q, Liu, T, Zhang, C, Liu, Z, Zheng, W, Ou, R, et al.. Extraordinary solution-processability of lignin in phenol–maleic anhydride and dielectric films with controllable properties. J Mater Chem 2019;7:23162–72. https://doi.org/10.1039/c9ta06665a.Search in Google Scholar
99. Kim, WG. Photocure properties of high-heat-resistant photoreactive polymers with cinnamate groups. J Appl Polym Sci 2008;107:3615–24. https://doi.org/10.1002/app.27436.Search in Google Scholar
100. Xin, J, Zhang, P, Huang, K, Zhang, J. Study of green epoxy resins derived from renewable cinnamic acid and dipentene: synthesis, curing and properties. RSC Adv 2014;4:8525–32. https://doi.org/10.1039/c3ra47927g.Search in Google Scholar
101. Kaneko, T, Matsusaki, M, Hang, TT, Akashi, M. Thermotropic liquid-crystalline polymer derived from natural cinnamoyl biomonomers. Macromol Rapid Commun 2004;25:673–7. https://doi.org/10.1002/marc.200300143.Search in Google Scholar
102. Kaneko, T, Thi, TH, Shi, DJ, Akashi, M. Environmentally degradable, high-performance thermoplastics from phenolic phytomonomers. Nat Mater 2006;5:966–70. https://doi.org/10.1038/nmat1778.Search in Google Scholar PubMed
103. Matsusaki, M, Kishida, A, Stainton, N, Ansell, CW, Akashi, M. Synthesis and characterization of novel biodegradable polymers composed of hydroxycinnamic acid and d, l-lactic acid. J Appl Polym Sci 2001;82:2357–64. https://doi.org/10.1002/app.2085.Search in Google Scholar
104. Spiliopoulos, IK, Mikroyannidis, JA. Unsaturated polyamides and polyesters prepared from 1, 4-bis (2-carboxyvinyl) benzene and 4-hydroxycinnamic acid. J Polym Sci Polym Chem 1996;34:2799–807. https://doi.org/10.1002/(sici)1099-0518(19960930)34:13<2799::aid-pola26>3.0.co;2-6.10.1002/(SICI)1099-0518(19960930)34:13<2799::AID-POLA26>3.0.CO;2-6Search in Google Scholar
105. Thi, TH, Matsusaki, M, Akashi, M. Thermally stable and photoreactive polylactides by the terminal conjugation of bio-based caffeic acid. Chem Commun 2008:3918–20.10.1039/b803615bSearch in Google Scholar
106. Thi, TH, Matsusaki, M, Akashi, M. Development of photoreactive degradable branched polyesters with high thermal and mechanical properties. Biomacromolecules 2009;10:766–72. https://doi.org/10.1021/bm801203g.Search in Google Scholar PubMed
107. Nagata, M, Hizakae, S. Synthesis and characterization of photocrosslinkable biodegradable polymers derived from 4-hydroxycinnamic acid. Macromol Biosci 2003;3:412–9. https://doi.org/10.1002/mabi.200350011.Search in Google Scholar
108. Truong, HT, Van Do, M, Duc Huynh, L, Thi Nguyen, L, Tuan Do, A, Thanh Xuan Le, T, et al.. Ultrasound-Assisted, base-catalyzed, homogeneous reaction for ferulic acid production from γ-oryzanol. J Chem 2018;2018:1–9. https://doi.org/10.1155/2018/3132747.Search in Google Scholar
109. Huang, Y-C, Chen, Y-F, Chen, C-Y, Chen, W-L, Ciou, Y-P, Liu, W-H, et al.. Production of ferulic acid from lignocellulolytic agricultural biomass by Thermobifida fusca thermostable esterase produced in Yarrowia lipolytica transformant. Bioresour Technol 2011;102:8117–22. https://doi.org/10.1016/j.biortech.2011.05.062.Search in Google Scholar PubMed
110. Oulame, MZ, Pion, F, Allauddin, S, Raju, KV, Ducrot, P-H, Allais, F. Renewable alternating aliphatic-aromatic poly (ester-urethane) s prepared from ferulic acid and bio-based diols. Eur Polym J 2015;63:186–93. https://doi.org/10.1016/j.eurpolymj.2014.11.031.Search in Google Scholar
111. Chen, Q, Gao, K, Peng, C, Xie, H, Zhao, ZK, Bao, M. Preparation of lignin/glycerol-based bis (cyclic carbonate) for the synthesis of polyurethanes. Green Chem 2015;17:4546–51. https://doi.org/10.1039/c5gc01340b.Search in Google Scholar
112. Ghosh, N, Kiskan, B, Yagci, Y. Polybenzoxazines—new high performance thermosetting resins: synthesis and properties. Prog Polym Sci 2007;32:1344–91. https://doi.org/10.1016/j.progpolymsci.2007.07.002.Search in Google Scholar
113. Comí, M, Lligadas, G, Ronda, JC, Galià, M, Cádiz, V. Renewable benzoxazine monomers from “lignin-like” naturally occurring phenolic derivatives. J Polym Sci Polym Chem 2013;51:4894–903. https://doi.org/10.1002/pola.26918.Search in Google Scholar
114. GREGoRová, A, Kosikova, B, Osvald, A. The study of lignin influence on properties of polypropylene composites. Wood Res 2005;50:41–8.Search in Google Scholar
115. Košíková, B, Demianova, V, Kačuráková, M. Sulfur-free lignins as composites of polypropylene films. J Appl Polym Sci 1993;47:1065–73.10.1002/app.1993.070470613Search in Google Scholar
116. Yue, X, Chen, F, Zhou, X. Synthesis of lignin-g-MMA and the utilization of the copolymer in PVC/wood composites. J Macromol Sci B 2012;51:242–54. https://doi.org/10.1080/00222348.2011.585328.Search in Google Scholar
117. Baumberger, S, Lapierre, C, Monties, B. Utilization of pine Kraft lignin in starch composites: impact of structural heterogeneity. J Agric Food Chem 1998;46:2234–40. https://doi.org/10.1021/jf971067h.Search in Google Scholar
118. Kadla, J, Kubo, S, Venditti, R, Gilbert, R, Compere, A, Griffith, W. Lignin-based carbon fibers for composite fiber applications. Carbon 2002;40:2913–20. https://doi.org/10.1016/s0008-6223(02)00248-8.Search in Google Scholar
119. Megiatto, JDJr, Silva, CG, Rosa, DS, Frollini, E. Sisal chemically modified with lignins: correlation between fibers and phenolic composites properties. Polym Degrad Stabil 2008;93:1109–21. https://doi.org/10.1016/j.polymdegradstab.2008.03.011.Search in Google Scholar
120. Nenkova, SK. Study of sorption properties of lignin-derivatized fibrous composites for the remediation of oil polluted receiving waters. BioResources 2007;2:408–18.10.15376/biores.2.4.408-418Search in Google Scholar
121. Morandim-Giannetti, AA, Agnelli, JAM, Lanças, BZ, Magnabosco, R, Casarin, SA, Bettini, SH. Lignin as additive in polypropylene/coir composites: thermal, mechanical and morphological properties. Carbohydr Polym 2012;87:2563–8. https://doi.org/10.1016/j.carbpol.2011.11.041.Search in Google Scholar
122. Pupure, L, Varna, J, Joffe, R, Pupurs, A. An analysis of the nonlinear behavior of lignin-based flax composites. Mech Compos Mater 2013;49:139–54. https://doi.org/10.1007/s11029-013-9330-x.Search in Google Scholar
123. Canetti, M, Bertini, F. Influence of the lignin on thermal degradation and melting behaviour of poly (ethylene terephthalate) based composites. E-Polymers 2009;9:1–10. https://doi.org/10.1515/epoly.2009.9.1.596.Search in Google Scholar
124. Reza Barzegari, M, Alemdar, A, Zhang, Y, Rodrigue, D. Mechanical and rheological behavior of highly filled polystyrene with lignin. Polym Compos 2012;33:353–61. https://doi.org/10.1002/pc.22154.Search in Google Scholar
125. Sun, R. Across the board: runcang sun on lignin nanoparticles. ChemSusChem 2020;13:4768–70. https://doi.org/10.1002/cssc.202000755.Search in Google Scholar PubMed
126. Akato, K, Tran, CD, Chen, J, Naskar, AK. Poly(ethylene oxide)-assisted macromolecular self-assembly of lignin in ABS matrix for sustainable composite applications. ACS Sustain Chem Eng 2015;3:3070–6. https://doi.org/10.1021/acssuschemeng.5b00509.Search in Google Scholar
127. Wang, H-M, Wang, B, Yuan, T-Q, Zheng, L, Shi, Q, Wang, S-F, et al.. Tunable, UV-shielding and biodegradable composites based on well-characterized lignins and poly(butylene adipate-co-terephthalate). Green Chem 2020;22:8623–32. https://doi.org/10.1039/d0gc03284k.Search in Google Scholar
128. Zhang, X, Liu, W, Yang, D, Qiu, X. Biomimetic supertough and strong biodegradable. polymeric materials with improved thermal properties and excellent UV-blocking performance. Adv Funct Mater 2019;29:1806912. https://doi.org/10.1002/adfm.201806912.Search in Google Scholar
129. Xiao, S, Feng, J, Zhu, J, Wang, X, Yi, C, Su, S. Preparation and characterization of lignin-layered double hydroxide/styrene-butadiene rubber composites. J Appl Polym Sci 2013;130:1308–12. https://doi.org/10.1002/app.39311.Search in Google Scholar
130. Jiang, C, He, H, Jiang, H, Ma, L, Jia, D. Nano-lignin filled natural rubber composites: preparation and characterization. Express Polym Lett 2013;7:480–93. https://doi.org/10.3144/expresspolymlett.2013.44.Search in Google Scholar
131. Zhang, J, Fleury, E, Brook, MA. Foamed lignin–silicone bio-composites by extrusion and then compression molding. Green Chem 2015;17:4647–56. https://doi.org/10.1039/c5gc01418b.Search in Google Scholar
132. Zhang, J, Chen, Y, Sewell, P, Brook, MA. Utilization of softwood lignin as both crosslinker and reinforcing agent in silicone elastomers. Green Chem 2015;17:1811–9. https://doi.org/10.1039/c4gc02409e.Search in Google Scholar
133. Tran, CD, Chen, J, Keum, JK, Naskar, AK. A new class of renewable thermoplastics with extraordinary performance from nanostructured lignin-elastomers. Adv Funct Mater 2016;26:2677–85. https://doi.org/10.1002/adfm.201504990.Search in Google Scholar
134. Khalil, HA, Marliana, M, Alshammari, T. Material properties of epoxy-reinforced biocomposites with lignin from empty fruit bunch as curing agent. BioResources 2011;6:5206–23.10.15376/biores.6.4.5206-5223Search in Google Scholar
135. Doherty, W, Halley, P, Edye, L, Rogers, D, Cardona, F, Park, Y, et al.. Studies on polymers and composites from lignin and fiber derived from sugar cane. Polym Adv Technol 2007;18:673–8. https://doi.org/10.1002/pat.879.Search in Google Scholar
136. Stanzione, JFIII, Giangiulio, PA, Sadler, JM, La Scala, JJ, Wool, RP. Lignin-based bio-oil mimic as biobased resin for composite applications. ACS Sustain Chem Eng 2013;1:419–26. https://doi.org/10.1021/sc3001492.Search in Google Scholar
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