Abstract
This chapter presents the most recent updates about sol-gel chemistry of phenolic molecules and the corresponding materials: xerogels, cryogels, and aerogels. The structure and properties of the latter, whether in the organic or carbon forms, are detailed and actual and potential applications are reported.
After an introduction about plant polyphenols in general, the focus is mainly given to condensed (flavonoid) tannins, shown to be the most relevant raw material for preparing resins, and hence gels. Lignin is considered as well, despite its lower reactivity and its less reproducible character, because of its industrial importance. Details about the nature and the properties of the carbon that can be obtained by pyrolysis of crosslinked polyphenols are also given.
Tannin-formaldehyde resins and mixed formulations associating resorcinol, soy protein, lignin, phenol, or surfactant are then discussed in terms of reactivity and ability to produce highly porous gels, depending on the experimental conditions of synthesis (dilution, pH, amount of crosslinker, etc.) and drying (subcritical, supercritical, or lyophilization). The porous structure of those materials is also explained in relation to gelation time and mechanical properties of the corresponding hydrogels. Derived carbons gels, including N-doped, formaldehyde-free materials, and activated carbon gels, are also considered.
Mechanical and thermal properties of organic gels, as well as electrochemical properties of carbon gels, are next introduced. Finally, recent developments including one-step microwave synthesis of xerogels, carbon xerogel microspheres having the characteristics of carbon molecular sieves, and elastic gels behaving as rubber springs with tunable elastic properties, all biosourced and tannin-based, are presented.
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References
B. Babić, B. Kaluđerović, L. Vračar, N. Krstajić, Characterization of carbon cryogel synthesized by sol–gel polycondensation and freeze-drying. Carbon 42, 2617–2624 (2004). https://doi.org/10.1016/j.carbon.2004.05.046
R.B. Durairaj, Resorcinol: Chemistry, Technology and Applications (Springer, Berlin, 2005)
D. Fairén-Jiménez, F. Carrasco-Marín, C. Moreno-Castilla, Porosity and surface area of monolithic carbon aerogels prepared using alkaline carbonates and organic acids as polymerization catalysts. Carbon 44, 2301–2307 (2006). https://doi.org/10.1016/j.carbon.2006.02.021
J. Fricke, Aerogels: Proceedings of the First International Symposium, Würzburg, Fed. Rep. of Germany September 23–25, 1985 (Springer, Berlin, 1986)
N. Job, R. Pirard, J. Marien, J.-P. Pirard, Porous carbon xerogels with texture tailored by pH control during sol–gel process. Carbon 42, 619–628 (2004). https://doi.org/10.1016/j.carbon.2003.12.072
A. Léonard, N. Job, S. Blacher, et al., Suitability of convective air drying for the production of porous resorcinol–formaldehyde and carbon xerogels. Carbon 43, 1808–1811 (2005). https://doi.org/10.1016/j.carbon.2005.02.016
R.W. Pekala, Organic aerogels from the polycondensation of resorcinol with formaldehyde. J. Mater. Sci. 24, 3221–3227 (1989). https://doi.org/10.1007/BF01139044
H. Tamon, H. Ishizaka, T. Yamamoto, T. Suzuki, Preparation of mesoporous carbon by freeze drying. Carbon 37, 2049–2055 (1999). https://doi.org/10.1016/S0008-6223(99)00089-5
K.-N. Lee, H.-J. Lee, J.-H. Kim, Synthesis of phenolic/furfural gel microspheres in supercritical CO2. J. Supercrit. Fluids 17, 73–80 (2000). https://doi.org/10.1016/S0896-8446(99)00041-8
R.W. Pekala, C.T. Alviso, X. Lu, et al., New organic aerogels based upon a phenolic-furfural reaction. J. Non-Cryst. Solids 188, 34–40 (1995). https://doi.org/10.1016/0022-3093(95)00027-5
A. Szczurek, K. Jurewicz, G. Amaral-Labat, et al., Structure and electrochemical capacitance of carbon cryogels derived from phenol–formaldehyde resins. Carbon 48, 3874–3883 (2010). https://doi.org/10.1016/j.carbon.2010.06.053
D. Wu, R. Fu, Z. Sun, Z. Yu, Low-density organic and carbon aerogels from the sol–gel polymerization of phenol with formaldehyde. J. Non-Cryst. Solids 351, 915–921 (2005). https://doi.org/10.1016/j.jnoncrysol.2005.02.008
W.-C. Li, A.-H. Lu, S.-C. Guo, Characterization of the microstructures of organic and carbon aerogels based upon mixed cresol–formaldehyde. Carbon 39, 1989–1994 (2001). https://doi.org/10.1016/S0008-6223(01)00029-X
G. Amaral-Labat, A. Szczurek, V. Fierro, et al., in Turning adhesive formulations into valuable carbon gels. Proceedings of the International Conference Carbon’13. Rio de Janeiro (Brasil), 2013
E. Scopelitis, A. Pizzi, The chemistry and development of branched PRF wood adhesives of low resorcinol content. J. Appl. Polym. Sci. 47, 351–360 (1993). https://doi.org/10.1002/app.1993.070470215
G. Amaral-Labat, A. Szczurek, V. Fierro, et al., “Blue glue”: a new precursor of carbon aerogels. Microporous Mesoporous Mater. 158, 272–280 (2012). https://doi.org/10.1016/j.micromeso.2012.03.051
W.H.L. Dornette, M.E. Woodworth, Proposed amendments on revisions to the recommended system for the identification of the fire hazards of materials. NFPA No. 704M-1969. https://www.nfpa.org/Assets/files/AboutTheCodes/704/TCRF-1975-704M.pdf. Accessed 27 May 2018
R.V. Barbehenn, C.P. Constabel, Tannins in plant–herbivore interactions. Phytochemistry 72, 1551–1565 (2011). https://doi.org/10.1016/j.phytochem.2011.01.040
G.G. Gross, Biosynthesis of hydrolyzable tannins, in Comprehensive Natural Products Chemistry: Carbohydrates and Their Derivatives Including Tannins, Cellulose and Related Lignings, ed. by S.D. Barton, K. Nakanishi, O. Meth-Cohn (Pergamon, Oxford, 1999), pp. 799–826
K. Khanbabaee, R.T. van, Tannins: classification and definition. Nat. Prod. Rep. 18, 641–649 (2001). https://doi.org/10.1039/B101061L
F.L. Braghiroli, V. Fierro, M.T. Izquierdo, et al., Nitrogen-doped carbon materials produced from hydrothermally treated tannin. Carbon 50, 5411–5420 (2012). https://doi.org/10.1016/j.carbon.2012.07.027
A. Pizzi, Tannin-based wood adhesives, in Wood Adhesives: Chemistry and Technology, 1st edn. (CRC Press, New York, 1983), pp. 177–246
A. Pizzi, H. Pasch, A. Celzard, A. Szczurek, Oligomers distribution at the gel point of tannin–formaldehyde thermosetting adhesives for wood panels. J. Adhes. Sci. Technol. 27, 2094–2102 (2013). https://doi.org/10.1080/01694243.2012.697669
C. Lacoste, M.C. Basso, A. Pizzi, et al., Pine tannin-based rigid foams: mechanical and thermal properties. Ind. Crop. Prod. 43, 245–250 (2013). https://doi.org/10.1016/j.indcrop.2012.07.039
A. Pizzi, K.L. Mittal, Handbook of Adhesive Technology, Revised and Expanded (Marcel Dekker, New York, 2003)
C. Lacoste, M.C. Basso, A. Pizzi, et al., Bioresourced pine tannin/furanic foams with glyoxal and glutaraldehyde. Ind. Crop. Prod. 45, 401–405 (2013). https://doi.org/10.1016/j.indcrop.2012.12.032
X. Li, A. Pizzi, X. Zhou, et al., Formaldehyde-free prorobitenidin/profi setinidin tannin/furanic foams based on alternative aldehydes: glyoxal and glutaraldehyde. J. Renew. Mater. 3, 142–150 (2015). https://doi.org/10.7569/JRM.2014.634117
A. Szczurek, V. Fierro, A. Pizzi, et al., A new method for preparing tannin-based foams. Ind. Crop. Prod. 54, 40–53 (2014). https://doi.org/10.1016/j.indcrop.2014.01.012
A. Szczurek, V. Fierro, A. Pizzi, et al., Corrigendum to “A new method for preparing tannin-based foams” [Ind. Crops Prod. 54, 40–53]. Ind. Crop. Prod. 67, 510 (2015). https://doi.org/10.1016/j.indcrop.2015.02.030
M.C. Basso, X. Li, V. Fierro, et al., Green, formaldehyde-free, foams for thermal insulation. Adv. Mater. Lett. 2, 378–382 (2011). https://doi.org/10.5185/amlett.2011.4254
A. Szczurek, V. Fierro, M. Thébault, et al., Structure and properties of poly(furfuryl alcohol)-tannin polyHIPEs. Eur. Polym. J. 78, 195–212 (2016). https://doi.org/10.1016/j.eurpolymj.2016.03.037
A. Pizzi, G. Tondi, H. Pasch, A. Celzard, Matrix-assisted laser desorption/ionization time-of-flight structure determination of complex thermoset networks: polyflavonoid tannin–furanic rigid foams. J. Appl. Polym. Sci. 110, 1451–1456 (2008). https://doi.org/10.1002/app.28545
X. Li, M.C. Basso, V. Fierro, et al., Chemical modification of tannin/furanic rigid foams by isocyanates and polyurethanes. Maderas Cienc. Tecnol. 14, 257–265 (2012). https://doi.org/10.4067/S0718-221X2012005000001
X. Li, A. Pizzi, M. Cangemi, et al., Insulation rigid and elastic foams based on albumin. Ind. Crop. Prod. 37, 149–154 (2012). https://doi.org/10.1016/j.indcrop.2011.11.030
X. Li, A. Pizzi, M. Cangemi, et al., Flexible natural tannin-based and protein-based biosourced foams. Ind. Crop. Prod. 37, 389–393 (2012). https://doi.org/10.1016/j.indcrop.2011.12.037
F. Braghiroli, V. Fierro, A. Pizzi, et al., Reaction of condensed tannins with ammonia. Ind. Crop. Prod. 44, 330–335 (2013). https://doi.org/10.1016/j.indcrop.2012.11.024
X. Li, H.A. Essawy, A. Pizzi, et al., Modification of tannin based rigid foams using oligomers of a hyperbranched poly(amine-ester). J. Polym. Res. 19, 21 (2012). https://doi.org/10.1007/s10965-012-0021-4
M.C. Basso, S. Giovando, A. Pizzi, et al., Flexible-elastic copolymerized polyurethane-tannin foams. J. Appl. Polym. Sci. 131, 40499–1-40499–6 (2014). https://doi.org/10.1002/app.40499
M. Basso, A. Pizzi, C. Lacoste, et al., MALDI-TOF and 13C NMR analysis of tannin–furanic–polyurethane foams adapted for industrial continuous lines application. Polymers 6, 2985–3004 (2014). https://doi.org/10.3390/polym6122985
C. Lacoste, M.C. Basso, A. Pizzi, et al., Natural albumin/tannin cellular foams. Ind. Crop. Prod. 73, 41–48 (2015). https://doi.org/10.1016/j.indcrop.2015.03.087
F.-J. Santiago-Medina, A. Pizzi, M.C. Basso, et al., Polycondensation resins by flavonoid tannins reaction with amines. Polymers 9, 37 (2017). https://doi.org/10.3390/polym9020037
A. Arbenz, L. Avérous, Chemical modification of tannins to elaborate aromatic biobased macromolecular architectures. Green Chem. 17, 2626–2646 (2015). https://doi.org/10.1039/C5GC00282F
A. Pizzi, H. Pasch, A. Celzard, A. Szczurek, Oligomer distribution at the gel point of tannin-resorcinol-formaldehyde cold-set wood adhesives. J. Adhes. Sci. Technol. 26, 79–88 (2012). https://doi.org/10.1163/016942411X569309
A. Celzard, V. Fierro, A. Pizzi, W. Zhao, Multifunctional porous solids derived from tannins. J. Phys. Conf. Ser. 416, 012023 (2013). https://doi.org/10.1088/1742-6596/416/1/012023
A. Celzard, A. Szczurek, P. Jana, et al., Latest progresses in the preparation of tannin-based cellular solids. J. Cell. Plast. 51, 89–102 (2014). https://doi.org/10.1177/0021955X14538273
G. Tondi, W. Zhao, A. Pizzi, et al., Tannin-based rigid foams: a survey of chemical and physical properties. Bioresour. Technol. 100, 5162–5169 (2009). https://doi.org/10.1016/j.biortech.2009.05.055
W. Zhao, A. Pizzi, V. Fierro, et al., Effect of composition and processing parameters on the characteristics of tannin-based rigid foams. Part I: cell structure. Mater. Chem. Phys. 122, 175–182 (2010). https://doi.org/10.1016/j.matchemphys.2010.02.062
W. Zhao, V. Fierro, A. Pizzi, et al., Effect of composition and processing parameters on the characteristics of tannin-based rigid foams. Part II: physical properties. Mater. Chem. Phys. 123, 210–217 (2010). https://doi.org/10.1016/j.matchemphys.2010.03.084
A. Celzard, W. Zhao, A. Pizzi, V. Fierro, Mechanical properties of tannin-based rigid foams undergoing compression. Mater. Sci. Eng. A 527, 4438–4446 (2010). https://doi.org/10.1016/j.msea.2010.03.091
A. Celzard, V. Fierro, G. Amaral-Labat, et al., Flammability assessment of tannin-based cellular materials. Polym. Degrad. Stab. 96, 477–482 (2011). https://doi.org/10.1016/j.polymdegradstab.2011.01.014
X. Zhou, A. Pizzi, A. Sauget, et al., Lightweight tannin foam/composites sandwich panels and the coldset tannin adhesive to assemble them. Ind. Crop. Prod. 43, 255–260 (2013). https://doi.org/10.1016/j.indcrop.2012.07.020
X. Li, A. Pizzi, C. Lacoste, et al., Physical properties of tannin/furanic resin foamed with different blowing agents. Bioresources 8, 743–752 (2012). https://doi.org/10.15376/biores.8.1.743-752
X. Li, V.K. Srivastava, A. Pizzi, et al., Nanotube-reinforced tannin/furanic rigid foams. Ind. Crop. Prod. 43, 636–639 (2013). https://doi.org/10.1016/j.indcrop.2012.08.008
M.C. Basso, S. Giovando, A. Pizzi, et al., Tannin/furanic foams without blowing agents and formaldehyde. Ind. Crop. Prod. 49, 17–22 (2013). https://doi.org/10.1016/j.indcrop.2013.04.043
M.C. Basso, A. Pizzi, A. Celzard, Dynamic monitoring of tannin-based foam preparation: effects of surfactant. Bioresources 8, 5807–5816 (2013). https://doi.org/10.15376/biores.8.4.5807-5816
M.C. Basso, A. Pizzi, A. Celzard, Influence of formulation on the dynamics of preparation of tannin-based foams. Ind. Crop. Prod. 51, 396–400 (2013). https://doi.org/10.1016/j.indcrop.2013.09.013
M.C. Basso, A. Pizzi, A. Celzard, Dynamic foaming behaviour of polyurethane vs tannin/furanic foams. J. Renew. Mater. 1, 273–278 (2013). https://doi.org/10.7569/JRM.2013.634125
C. Lacoste, A. Pizzi, M.-C. Basso, et al., Pinus pinaster tannin/furanic foams: part I. Formulation. Ind. Crop. Prod. 52, 450–456 (2014). https://doi.org/10.1016/j.indcrop.2013.10.044
A. Martinez de Yuso, M.C. Lagel, A. Pizzi, et al., Structure and properties of rigid foams derived from quebracho tannin. Mater. Des. 63, 208–212 (2014). https://doi.org/10.1016/j.matdes.2014.05.072
M.C. Basso, S. Giovando, A. Pizzi, et al., Alkaline tannin rigid foams. J. Renew. Mater. 2, 182–185 (2014). https://doi.org/10.7569/JRM.2013.634137
C. Lacoste, A. Pizzi, M.-P. Laborie, A. Celzard, Pinus pinaster tannin/furanic foams: part II. Physical properties. Ind. Crop. Prod. 61, 531–536 (2014). https://doi.org/10.1016/j.indcrop.2014.04.034
C. Lacoste, M.-C. Basso, A. Pizzi, et al., Pine (P. pinaster) and quebracho (S. lorentzii) tannin-based foams as green acoustic absorbers. Ind. Crop. Prod. 67, 70–73 (2015). https://doi.org/10.1016/j.indcrop.2014.12.018
C. Lacoste, M. Čop, K. Kemppainen, et al., Biobased foams from condensed tannin extracts from Norway spruce (Picea abies) bark. Ind. Crop. Prod. 73, 144–153 (2015). https://doi.org/10.1016/j.indcrop.2015.03.089
M.C. Basso, M.-C. Lagel, A. Pizzi, et al., First tools for tannin-furanic foams design. Bioresources 10, 5233–5241 (2015). https://doi.org/10.15376/biores.10.3.5233-5241
G. Rangel, H. Chapuis, M.-C. Basso, et al., Improving water repellence and friability of tannin-furanic foams by oil-grafted flavonoid tannins. Bioresources 11, 7754–7768 (2016). https://doi.org/10.15376/biores.11.3.7754-7768
C. Delgado-Sanchez, M. Letellier, V. Fierro, et al., Hydrophobisation of tannin-based foams by covalent grafting of silanes. Ind. Crop. Prod. 92, 116 (2016). https://doi.org/10.1016/j.indcrop.2016.08.002
C. Delgado-Sánchez, V. Fierro, S. Li, et al., Stability analysis of tannin-based foams using multiple light-scattering measurements. Eur. Polym. J. 87, 318–330 (2017). https://doi.org/10.1016/j.eurpolymj.2016.12.036
C. Delgado-Sánchez, F. Santiago-Medina, V. Fierro, et al., Optimisation of “green” tannin-furanic foams for thermal insulation by experimental design. Mater. Des. 139, 7–15 (2018). https://doi.org/10.1016/j.matdes.2017.10.064
F.J. Santiago-Medina, C. Delgado-Sánchez, M.C. Basso, et al., Mechanically blown wall-projected tannin-based foams. Ind. Crop. Prod. 113, 316–323 (2018). https://doi.org/10.1016/j.indcrop.2018.01.049
M.C. Lagel, Y.A.M. de, A. Pizzi, et al., Développement et caractérisation de mousses à base de tanins de Quebracho. Mater. Tech. 102, 104 (2014). https://doi.org/10.1051/mattech/2014007
G. Tondi, V. Fierro, A. Pizzi, A. Celzard, Tannin-based carbon foams. Carbon 47, 1480–1492 (2009). https://doi.org/10.1016/j.carbon.2009.01.041
G. Tondi, V. Fierro, A. Pizzi, A. Celzard, Erratum to ‘Tannin-based carbon foam’ [Carbon 47 (2009) 1480–1492]. Carbon 47, 2761 (2009). https://doi.org/10.1016/j.carbon.2009.06.020
G. Tondi, S. Blacher, A. Léonard, et al., X-ray microtomography studies of tannin-derived organic and carbon foams. Microsc. Microanal. 15, 384–394 (2009). https://doi.org/10.1017/S1431927609990444
A. Tony Pizzi, A. Celzard, V. Fierro, G. Tondi, Chemistry, morphology, microtomography and activation of natural and carbonized tannin foams for different applications. Macromol. Symp. 313-314, 100–111 (2012). https://doi.org/10.1002/masy.201250311
X. Li, M.C. Basso, F.L. Braghiroli, et al., Tailoring the structure of cellular vitreous carbon foams. Carbon 50, 2026–2036 (2012). https://doi.org/10.1016/j.carbon.2012.01.004
A. Celzard, G. Tondi, D. Lacroix, et al., Radiative properties of tannin-based, glasslike, carbon foams. Carbon 50, 4102–4113 (2012). https://doi.org/10.1016/j.carbon.2012.04.058
G. Amaral-Labat, M. Sahimi, A. Pizzi, et al., Mechanical properties of heat-treated organic foams. Phys. Rev. E 87, 032156 (2013). https://doi.org/10.1103/PhysRevE.87.032156
G. Amaral-Labat, E. Gourdon, V. Fierro, et al., Acoustic properties of cellular vitreous carbon foams. Carbon 58, 76–86 (2013). https://doi.org/10.1016/j.carbon.2013.02.033
P. Jana, V. Fierro, A. Pizzi, A. Celzard, Biomass-derived, thermally conducting, carbon foams for seasonal thermal storage. Biomass Bioenergy 67, 312–318 (2014). https://doi.org/10.1016/j.biombioe.2014.04.031
M. Letellier, V. Fierro, A. Pizzi, A. Celzard, Tortuosity studies of cellular vitreous carbon foams. Carbon 80, 193–202 (2014). https://doi.org/10.1016/j.carbon.2014.08.056
P. Jana, V. Fierro, A. Pizzi, A. Celzard, Thermal conductivity improvement of composite carbon foams based on tannin-based disordered carbon matrix and graphite fillers. Mater. Des. 83, 635–643 (2015). https://doi.org/10.1016/j.matdes.2015.06.057
M. Letellier, A. Szczurek, M.-C. Basso, et al., Preparation and structural characterisation of model cellular vitreous carbon foams. Carbon 112, 208–218 (2017). https://doi.org/10.1016/j.carbon.2016.11.017
M. Letellier, J. Macutkevic, D. Bychanok, et al., Modelling the physical properties of glasslike carbon foams. J. Phys. Conf. Ser. 879, 012014 (2017). https://doi.org/10.1088/1742-6596/879/1/012014
M. Letellier, C. Delgado-Sanchez, M. Khelifa, et al., Mechanical properties of model vitreous carbon foams. Carbon 116, 562–571 (2017). https://doi.org/10.1016/j.carbon.2017.02.020
M. Letellier, S. Ghaffari Mosanenzadeh, H. Naguib, et al., Acoustic properties of model cellular vitreous carbon foams. Carbon 119, 241–250 (2017). https://doi.org/10.1016/j.carbon.2017.04.049
G. Amaral-Labat, C. Zollfrank, A. Ortona, et al., Structure and oxidation resistance of micro-cellular Si–SiC foams derived from natural resins. Ceram. Int. 39, 1841–1851 (2013). https://doi.org/10.1016/j.ceramint.2012.08.032
A. Pizzi, C. Zollfrank, X. Li, et al., A SEM record of proteins-derived microcellular silicon carbide foams. J. Renew. Mater. 2, 230–234 (2014). https://doi.org/10.7569/JRM.2014.634114
A. Szczurek, V. Fierro, A. Pizzi, A. Celzard, Mayonnaise, whipped cream and meringue, a new carbon cuisine. Carbon 58, 245–248 (2013). https://doi.org/10.1016/j.carbon.2013.02.056
A. Szczurek, V. Fierro, A. Pizzi, et al., Carbon meringues derived from flavonoid tannins. Carbon 65, 214–227 (2013). https://doi.org/10.1016/j.carbon.2013.08.017
A. Szczurek, V. Fierro, A. Pizzi, A. Celzard, Emulsion-templated porous carbon monoliths derived from tannins. Carbon 74, 352–362 (2014). https://doi.org/10.1016/j.carbon.2014.03.047
A. Szczurek, A. Martinez de Yuso, V. Fierro, et al., Tannin-based monoliths from emulsion-templating. Mater. Des. 79, 115–126 (2015). https://doi.org/10.1016/j.matdes.2015.04.020
W. Zhao, V. Fierro, A. Pizzi, A. Celzard, Bimodal cellular activated carbons derived from tannins. J. Mater. Sci. 45, 5778–5785 (2010). https://doi.org/10.1007/s10853-010-4651-9
F.L. Braghiroli, V. Fierro, M.T. Izquierdo, et al., Kinetics of the hydrothermal treatment of tannin for producing carbonaceous microspheres. Bioresour. Technol. 151, 271–277 (2014). https://doi.org/10.1016/j.biortech.2013.10.045
F.L. Braghiroli, V. Fierro, A. Szczurek, et al., Electrochemical performances of hydrothermal tannin-based carbons doped with nitrogen. Ind. Crop. Prod. 70, 332–340 (2015). https://doi.org/10.1016/j.indcrop.2015.03.046
F.L. Braghiroli, V. Fierro, M.T. Izquierdo, et al., High surface – highly N-doped carbons from hydrothermally treated tannin. Ind. Crop. Prod. 66, 282–290 (2015). https://doi.org/10.1016/j.indcrop.2014.11.022
F.L. Braghiroli, V. Fierro, J. Parmentier, et al., Hydrothermal carbons produced from tannin by modification of the reaction medium: addition of H+ and Ag+. Ind. Crop. Prod. 77, 364–374 (2015). https://doi.org/10.1016/j.indcrop.2015.09.010
S. Schaefer, A. Ramirez, R. Mallada, et al., Easy preparation of tannin-based Ag catalysts for ethylene epoxidation. ChemistrySelect 2, 8509–8516 (2017). https://doi.org/10.1002/slct.201701548
F.L. Braghiroli, V. Fierro, A. Szczurek, et al., Hydrothermal treatment of tannin: a route to porous metal oxides and metal/carbon hybrid materials. Inorganics 5, 7 (2017). https://doi.org/10.3390/inorganics5010007
S. Schlienger, A.-L. Graff, A. Celzard, J. Parmentier, Direct synthesis of ordered mesoporous polymer and carbon materials by a biosourced precursor. Green Chem. 14, 313–316 (2012). https://doi.org/10.1039/C2GC16160E
F.L. Braghiroli, V. Fierro, J. Parmentier, et al., Easy and eco-friendly synthesis of ordered mesoporous carbons by self-assembly of tannin with a block copolymer. Green Chem. 18, 3265–3271 (2016). https://doi.org/10.1039/C5GC02788H
D. Bychanok, S. Li, G. Gorokhov, et al., Fully carbon metasurface: absorbing coating in microwaves. J. Appl. Phys. 121, 165103–1–165103–9 (2017). https://doi.org/10.1063/1.4982232
A. Szczurek, G. Amaral-Labat, V. Fierro, et al., New families of carbon gels based on natural resources. J. Phys. Conf. Ser. 416, 012022 (2013). https://doi.org/10.1088/1742-6596/416/1/012022
A. Pizzi, H.O. Scharfetter, The chemistry and development of tannin-based adhesives for exterior plywood. J. Appl. Polym. Sci. 22, 1745–1761 (1978). https://doi.org/10.1002/app.1978.070220623
M.C. Lagel, A. Pizzi, S. Giovando, A. Celzard, Development and characterisation of phenolic foams with phenol-formaldehyde-chestnut tannins resin. J. Renew. Mater. 2, 220–229 (2014). https://doi.org/10.7569/JRM.2014.634113
W.-J. Liu, H. Jiang, H.-Q. Yu, Thermochemical conversion of lignin to functional materials: a review and future directions. Green Chem. 17, 4888–4907 (2015). https://doi.org/10.1039/C5GC01054C
M.N. Mohamad Ibrahim, N. Zakaria, C.S. Sipaut, et al., Chemical and thermal properties of lignins from oil palm biomass as a substitute for phenol in a phenol formaldehyde resin production. Carbohydr. Polym. 86, 112–119 (2011). https://doi.org/10.1016/j.carbpol.2011.04.018
D. Saidane, J.-C. Barbe, M. Birot, H. Deleuze, Preparation of functionalized Kraft lignin beads. J. Appl. Polym. Sci. 116, 1184–1189 (2010). https://doi.org/10.1002/app.31659
G. Tondi, A. Pizzi, H. Pasch, A. Celzard, Structure degradation, conservation and rearrangement in the carbonisation of polyflavonoid tannin/furanic rigid foams—a MALDI-TOF investigation. Polym. Degrad. Stab. 93, 968–975 (2008). https://doi.org/10.1016/j.polymdegradstab.2008.01.024
G. Tondi, A. Pizzi, H. Pasch, et al., MALDI-ToF investigation of furanic polymer foams before and after carbonization: aromatic rearrangement and surviving furanic structures. Eur. Polym. J. 44, 2938–2943 (2008). https://doi.org/10.1016/j.eurpolymj.2008.06.029
G.M. Jenkins, K. Kawamura, Structure of glassy carbon. Nature 231, 175–176 (1971). https://doi.org/10.1038/231175a0
M. Shiraishi, in Tanso Zairyou Nyuumon, ed. by M. Inagaki (Kagakugizyutusha, Tokyo, 1984), p. 29
K. Jurkiewicz, Ł. Hawełek, K. Balin, et al., Conversion of natural tannin to hydrothermal and graphene-like carbons studied by wide-angle X-ray scattering. J. Phys. Chem. A 119, 8692–8701 (2015). https://doi.org/10.1021/acs.jpca.5b02407
C. Hu, S. Sedghi, A. Silvestre-Albero, et al., Raman spectroscopy study of the transformation of the carbonaceous skeleton of a polymer-based nanoporous carbon along the thermal annealing pathway. Carbon 85, 147–158 (2015). https://doi.org/10.1016/j.carbon.2014.12.098
A. Szczurek, G. Amaral-Labat, V. Fierro, et al., The use of tannin to prepare carbon gels. Part I: carbon aerogels. Carbon 49, 2773–2784 (2011). https://doi.org/10.1016/j.carbon.2011.03.007
U. Szeluga, S. Pusz, B. Kumanek, et al., Influence of unique structure of glassy carbon on morphology and properties of its epoxy-based binary composites and hybrid composites with carbon nanotubes. Compos. Sci. Technol. 134, 72–80 (2016). https://doi.org/10.1016/j.compscitech.2016.08.004
M. Inagaki, New Carbons - Control of Structure and Functions, 1st edn. (Elsevier Science, Oxford, 2000)
M.I. Nathan, J.E. Smith, K.N. Tu, Raman spectra of glassy carbon. J. Appl. Phys. 45, 2370–2370 (1974). https://doi.org/10.1063/1.1663599
A. Szczurek, A. Ortona, L. Ferrari, et al., Carbon periodic cellular architectures. Carbon 88, 70–85 (2015). https://doi.org/10.1016/j.carbon.2015.02.069
V.N. Tsaneva, W. Kwapinski, X. Teng, B.A. Glowacki, Assessment of the structural evolution of carbons from microwave plasma natural gas reforming and biomass pyrolysis using Raman spectroscopy. Carbon 80, 617–628 (2014). https://doi.org/10.1016/j.carbon.2014.09.005
A.C. Ferrari, J. Robertson, Interpretation of Raman spectra of disordered and amorphous carbon. Phys. Rev. B 61, 14095–14107 (2000). https://doi.org/10.1103/PhysRevB.61.14095
G. Amaral-Labat, A. Szczurek, V. Fierro, et al., Pore structure and electrochemical performances of tannin-based carbon cryogels. Biomass Bioenergy 39, 274–282 (2012). https://doi.org/10.1016/j.biombioe.2012.01.019
F.L. Braghiroli, V. Fierro, A. Szczurek, et al., Hydrothermally treated aminated tannin as precursor of N-doped carbon gels for supercapacitors. Carbon 90, 63–74 (2015). https://doi.org/10.1016/j.carbon.2015.03.038
A. Sánchez-Sánchez, M.T. Izquierdo, J. Ghanbaja, et al., Excellent electrochemical performances of nanocast ordered mesoporous carbons based on tannin-related polyphenols as supercapacitor electrodes. J. Power Sources 344, 15–24 (2017). https://doi.org/10.1016/j.jpowsour.2017.01.099
V. Fierro, A. Sanchez-Sanchez, A. Celzard, Tannins as precursors of supercapacitor electrodes, in Sustainable Energy Technologies, ed. by E. Rincón-Mejía, A. de las Heras (CRC Press, Taylor & Francis, Boca Raton, 2017), pp. 201–228
L. Soukup, I. Gregora, L. Jastrabik, A. Koňáková, Raman spectra and electrical conductivity of glassy carbon. Mater. Sci. Eng. B 11, 355–357 (1992). https://doi.org/10.1016/0921-5107(92)90240-A
P.P. Kuzhir, A.G. Paddubskaya, M.V. Shuba, et al., Electromagnetic shielding efficiency in Ka-band: carbon foam versus epoxy/carbon nanotube composites. J. Nanophotonics 6, 061715 (2012). https://doi.org/10.1117/1.JNP.6.061715
M. Letellier, J. Macutkevic, A. Paddubskaya, et al., Tannin-based carbon foams for electromagnetic applications. IEEE Trans. Electromagn. Compat. 57, 989–995 (2015). https://doi.org/10.1109/TEMC.2015.2430370
M. Letellier, J. Macutkevic, A. Paddubskaya, et al., Microwave dielectric properties of tannin-based carbon foams. Ferroelectrics 479, 119–126 (2015). https://doi.org/10.1080/00150193.2015.1012036
M. Letellier, J. Macutkevic, P. Kuzhir, et al., Electromagnetic properties of model vitreous carbon foams. Carbon 122, 217–227 (2017). https://doi.org/10.1016/j.carbon.2017.06.080
M. Seredych, A. Szczurek, V. Fierro, et al., Electrochemical reduction of oxygen on hydrophobic ultramicroporous polyHIPE carbon. ACS Catal. 6, 5618–5628 (2016). https://doi.org/10.1021/acscatal.6b01497
J. Encalada, K. Savaram, N.A. Travlou, et al., Combined effect of porosity and surface chemistry on the electrochemical reduction of oxygen on cellular vitreous carbon foam catalyst. ACS Catal. 7, 7466–7478 (2017). https://doi.org/10.1021/acscatal.7b01977
L.I. Grishechko, G. Amaral-Labat, V. Fierro, et al., Biosourced, highly porous, carbon xerogel microspheres. RSC Adv. 6, 65698–65708 (2016). https://doi.org/10.1039/C6RA09462G
C.J. Brinker, G.W. Scherer, Sol-Gel Science: The Physics and Chemistry of Sol-Gel Processing (Academic Press, San Diego, 1990)
A. Szczurek, G. Amaral-Labat, V. Fierro, et al., Porosity of resorcinol-formaldehyde organic and carbon aerogels exchanged and dried with supercritical organic solvents. Mater. Chem. Phys. 129, 1221–1232 (2011). https://doi.org/10.1016/j.matchemphys.2011.06.021
G. Amaral-Labat, A. Szczurek, V. Fierro, et al., Impact of depressurizing rate on the porosity of aerogels. Microporous Mesoporous Mater. 152, 240–245 (2012). https://doi.org/10.1016/j.micromeso.2011.11.023
İ.A. Şengil, M. Özacar, Biosorption of Cu(II) from aqueous solutions by mimosa tannin gel. J. Hazard. Mater. 157, 277–285 (2008). https://doi.org/10.1016/j.jhazmat.2007.12.115
T. Ogata, Y. Nakano, Mechanisms of gold recovery from aqueous solutions using a novel tannin gel adsorbent synthesized from natural condensed tannin. Water Res. 39, 4281–4286 (2005). https://doi.org/10.1016/j.watres.2005.06.036
K. Kraiwattanawong, S.R. Mukai, H. Tamon, A.W. Lothongkum, Preparation of carbon cryogels from wattle tannin and furfural. Microporous Mesoporous Mater. 98, 258–266 (2007). https://doi.org/10.1016/j.micromeso.2006.09.007
K. Kraiwattanawong, S.R. Mukai, H. Tamon, A.W. Lothongkum, Improvement of mesoporosity of carbon cryogels by acid treatment of hydrogels. Microporous Mesoporous Mater. 115, 432–439 (2008). https://doi.org/10.1016/j.micromeso.2008.02.016
A. Szczurek, G. Amaral-Labat, V. Fierro, et al., The use of tannin to prepare carbon gels. Part II. carbon cryogels. Carbon 49, 2785–2794 (2011). https://doi.org/10.1016/j.carbon.2011.03.005
G. Carlson, D. Lewis, K. McKinley, et al., Aerogel commercialization: technology, markets and costs. J. Non-Cryst. Solids 186, 372–379 (1995). https://doi.org/10.1016/0022-3093(95)00069-0
G. Amaral-Labat, A. Szczurek, V. Fierro, et al., Systematic studies of tannin–formaldehyde aerogels: preparation and properties. Sci. Technol. Adv. Mater. 14, 015001 (2013). https://doi.org/10.1088/1468-6996/14/1/015001
G. Reichenauer, Structural characterization of aerogels, in Aerogels Handbook, ed. by M.A. Aegerter, N. Leventis, M.M. Koebel (Springer, New York, 2011), pp. 449–498
G. Amaral-Labat, L.I. Grishechko, V. Fierro, et al., Tannin-based xerogels with distinctive porous structures. Biomass Bioenergy 56, 437–445 (2013). https://doi.org/10.1016/j.biombioe.2013.06.001
G. Amaral-Labat, A. Szczurek, V. Fierro, A. Celzard, Unique bimodal carbon xerogels from soft templating of tannin. Mater. Chem. Phys. 149-150, 193–201 (2015). https://doi.org/10.1016/j.matchemphys.2014.10.006
N. Rey-Raap, A. Szczurek, V. Fierro, et al., Advances in tailoring the porosity of tannin-based carbon xerogels. Ind. Crop. Prod. 82, 100–106 (2016). https://doi.org/10.1016/j.indcrop.2015.12.001
M. Haghgoo, A.A. Yousefi, M.J.Z. Mehr, Nano porous structure of resorcinol–formaldehyde xerogels and aerogels: effect of sodium dodecylbenzene sulfonate. Iran. Polym. J. 21, 211–219 (2012). https://doi.org/10.1007/s13726-012-0023-4
A. Celzard, V. Fierro, G. Amaral-Labat, Adsorption by carbon gels, in Novel Carbon Adsorbents, ed. by J.M.D. Tascón (Elsevier, Oxford, 2012), pp. 207–244
J.L. Figueiredo, M.F.R. Pereira, Carbon as catalyst, in Carbon Materials for Catalysis, ed. by P. Serp, J.L. Figueiredo (Wiley, Hoboken, 2008), pp. 127–217
A. Szczurek, G. Amaral-Labat, V. Fierro, et al., Chemical activation of tannin-based hydrogels by soaking in KOH and NaOH solutions. Microporous Mesoporous Mater. 196, 8–17 (2014). https://doi.org/10.1016/j.micromeso.2014.04.051
K. Hashida, R. Makino, S. Ohara, Amination of pyrogallol nucleus of condensed tannins and related polyphenols by ammonia water treatment. Holzforschung 63, 319–326 (2008). https://doi.org/10.1515/HF.2009.043
A. Sanchez-Sanchez, M.T. Izquierdo, S. Mathieu, et al., Outstanding electrochemical performance of highly N- and O-doped carbons derived from pine tannin. Green Chem. 19, 2653–2665 (2017). https://doi.org/10.1039/C7GC00491E
G.A. Amaral-Labat, A. Pizzi, A.R. Gonçalves, et al., Environment-friendly soy flour-based resins without formaldehyde. J. Appl. Polym. Sci. 108, 624–632 (2008). https://doi.org/10.1002/app.27692
G. Amaral-Labat, L. Grishechko, A. Szczurek, et al., Highly mesoporous organic aerogels derived from soy and tannin. Green Chem. 14, 3099–3106 (2012). https://doi.org/10.1039/C2GC36263E
A. Cayla, F. Rault, S. Giraud, et al., PLA with intumescent system containing lignin and ammonium polyphosphate for flame retardant textile. Polymers 8, 331 (2016). https://doi.org/10.3390/polym8090331
L.I. Grishechko, G. Amaral-Labat, A. Szczurek, et al., New tannin–lignin aerogels. Ind. Crop. Prod. 41, 347–355 (2013). https://doi.org/10.1016/j.indcrop.2012.04.052
W.L. Griffith, A.L. Compere, Separation of alcohols from solution by lignin gels. Sep. Sci. Technol. 43, 2396–2405 (2008). https://doi.org/10.1080/01496390802148571
M. Nishida, Y. Uraki, Y. Sano, Lignin gel with unique swelling property. Bioresour. Technol. 88, 81–83 (2003). https://doi.org/10.1016/S0960-8524(02)00264-X
T. Lindström, C. Söremark, L. Westman, Lignin gels as a medium in gel permeation chromatography. J. Appl. Polym. Sci. 21, 2873–2876 (1977). https://doi.org/10.1002/app.1977.070211102
C. Wang, Y. Xiong, B. Fan, et al., Cellulose as an adhesion agent for the synthesis of lignin aerogel with strong mechanical performance, sound-absorption and thermal insulation. Sci. Rep. 6, 32383 (2016). https://doi.org/10.1038/srep32383
V. Hemmilä, S. Adamopoulos, O. Karlsson, A. Kumar, Development of sustainable bio-adhesives for engineered wood panels – a review. RSC Adv. 7, 38604–38630 (2017). https://doi.org/10.1039/C7RA06598A
L.I. Grishechko, G. Amaral-Labat, A. Szczurek, et al., Lignin–phenol–formaldehyde aerogels and cryogels. Microporous Mesoporous Mater. 168, 19–29 (2013). https://doi.org/10.1016/j.micromeso.2012.09.024
R.W. Pekala, C.T. Alviso, J.D. LeMay, Organic aerogels: microstructural dependence of mechanical properties in compression. J. Non-Cryst. Solids 125, 67–75 (1990). https://doi.org/10.1016/0022-3093(90)90324-F
A. Sánchez-Sánchez, A. Martinez de Yuso, F.L. Braghiroli, et al., Sugarcane molasses as a pseudocapacitive material for supercapacitors. RSC Adv. 6, 88826–88836 (2016). https://doi.org/10.1039/C6RA16314A
A. Sánchez-Sánchez, V. Fierro, M.T. Izquierdo, A. Celzard, Functionalized, hierarchical and ordered mesoporous carbons for high-performance supercapacitors. J. Mater. Chem. A 4, 6140–6148 (2016). https://doi.org/10.1039/C6TA00738D
N. Rey-Raap, A. Szczurek, V. Fierro, et al., Towards a feasible and scalable production of bio-xerogels. J. Colloid Interface Sci. 456, 138–144 (2015). https://doi.org/10.1016/j.jcis.2015.06.024
J.L. Drury, D.J. Mooney, Hydrogels for tissue engineering: scaffold design variables and applications. Biomaterials 24, 4337–4351 (2003). https://doi.org/10.1016/S0142-9612(03)00340-5
N.A. Peppas, P. Bures, W. Leobandung, H. Ichikawa, Hydrogels in pharmaceutical formulations. Eur. J. Pharm. Biopharm. 50, 27–46 (2000). https://doi.org/10.1016/S0939-6411(00)00090-4
A.S. Hoffman, Hydrogels for biomedical applications. Adv. Drug Deliv. Rev. 64, 18–23 (2012). https://doi.org/10.1016/j.addr.2012.09.010
C. Delgado-Sánchez, G. Amaral-Labat, L.I. Grishechko, et al., Fire-resistant tannin–ethylene glycol gels working as rubber springs with tuneable elastic properties. J. Mater. Chem. A 5, 14720–14732 (2017). https://doi.org/10.1039/C7TA03768F
C. Delgado-Sánchez, J. Sarazin, F.J. Santiago-Medina, et al., Impact of the formulation of biosourced phenolic foams on their fire properties. Polym. Degrad. Stab. 153, 1–14 (2018). https://doi.org/10.1016/j.polymdegradstab.2018.04.006
G. Amaral-Labat, L.I. Grishechko, G.F.B. Lenz e Silva, et al., Rubber-like materials derived from biosourced phenolic resins. J. Phys. Conf. Ser. 879, 012013 (2017). https://doi.org/10.1088/1742-6596/879/1/012013
Acknowledgements
The authors gratefully acknowledge the financial support of the CPER 2007–2013 “Structuration du Pôle de Compétitivité Fibres Grand’Est” (Competitiveness Fibre Cluster), through local (Conseil Général des Vosges), regional (Région Lorraine), national (DRRT and FNADT), and European (FEDER) funds.
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Arenillas, A. et al. (2019). Organic and Carbon Gels Derived from Biosourced Polyphenols. In: Organic and Carbon Gels. Advances in Sol-Gel Derived Materials and Technologies. Springer, Cham. https://doi.org/10.1007/978-3-030-13897-4_2
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