Comparing Condensed and Hydrolysable Tannins for Mechanical Foaming of Furanic Foams: Synthesis and Characterization

J. Eckardt; T. Sepperer; E. Cesprini; P. Šket; G. Tondi

doi:10.3390/molecules28062799

Comparing Condensed and Hydrolysable Tannins for Mechanical Foaming of Furanic Foams: Synthesis and Characterization

J. Eckardt
, T. Sepperer
, E. Cesprini
, P. Šket
, G. Tondi

Design and Green Engineering

Department of Land, Environment, Agriculture and Forestry, University of Padua
National Institute of Chemistry Ljubljana

Research output: Contribution to journal › Article › peer-review

Abstract

This study examined the potential of hydrolysable tannin in comparison to condensed tannins for the production of furanic foams. The results indicate that chestnut tannin presents lower reactivity and requires a stronger acid for the polymerization. Additionally, foamability and density were found to be dependent on both surfactant concentration and tannin type, allowing lower densities for mimosa tannin and lower thermal conductivities for chestnut-based foams. Mimosa tannin was found to have the highest compression strength, followed by quebracho and chestnut, promising thermal conductivity of around 50 mW/m·K for 300 kg/m3 foams, which suggests that chestnut foams have the potential to performing highly when the density is reduced. Chemical analysis revealed that the methylene moieties of the furanics are non-specific and produces new covalent bonds with nucleophilic substrates: -OH groups and free-positions in the flavonoids. Overall, this study opens new perspectives for the application of hydrolysable tannins in polymer and material science.

Original language	English
Journal	Molecules
Volume	28
Issue number	6
DOIs	https://doi.org/10.3390/molecules28062799
Publication status	Published - 20 Mar 2023

Keywords

13CNMR analysis
ATR FT-IR
bio-based materials
bio-polymers
insulation
lightweight
natural extracts

Access to Document

10.3390/molecules28062799

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85151108635&doi=10.3390%2fmolecules28062799&partnerID=40&md5=1315d2424d3f8ec6ddc6aae4cbe087da

Cite this

@article{f363ec8af2424175b5afff44fde9a18a,

title = "Comparing Condensed and Hydrolysable Tannins for Mechanical Foaming of Furanic Foams: Synthesis and Characterization",

abstract = "This study examined the potential of hydrolysable tannin in comparison to condensed tannins for the production of furanic foams. The results indicate that chestnut tannin presents lower reactivity and requires a stronger acid for the polymerization. Additionally, foamability and density were found to be dependent on both surfactant concentration and tannin type, allowing lower densities for mimosa tannin and lower thermal conductivities for chestnut-based foams. Mimosa tannin was found to have the highest compression strength, followed by quebracho and chestnut, promising thermal conductivity of around 50 mW/m·K for 300 kg/m3 foams, which suggests that chestnut foams have the potential to performing highly when the density is reduced. Chemical analysis revealed that the methylene moieties of the furanics are non-specific and produces new covalent bonds with nucleophilic substrates: -OH groups and free-positions in the flavonoids. Overall, this study opens new perspectives for the application of hydrolysable tannins in polymer and material science.",

keywords = "13CNMR analysis, ATR FT-IR, bio-based materials, bio-polymers, insulation, lightweight, natural extracts",

author = "J. Eckardt and T. Sepperer and E. Cesprini and P. {\v S}ket and G. Tondi",

note = "Cited By :4 Export Date: 14 December 2023 CODEN: MOLEF Correspondence Address: Tondi, G.; TESAF Department, Viale dell{\textquoteright}Universit{\`a} 16, Italy; email: [email protected] Funding details: European Commission, EC Funding details: Ministero dell{\textquoteright}Istruzione, dell{\textquoteright}Universit{\`a} e della Ricerca, MIUR Funding details: Universit{\`a} degli Studi di Padova, UNIPD Funding text 1: The authors gratefully acknowledge the European Union and the Italian Ministry of University and Research for the support with the PhD PON project {\textquotedblleft}Development of sustainable tannin-based bio-foams for the thermal insulation of buildings{\textquotedblright} as well as the LERH doctoral school, the TESAF department of the University of Padua for the support of the project BIRD 2021 and the CERIC-ERIC Consortium for access to solid state C-NMR experimental facilities. 13 References: Pavel, C., Blagoeva, D., (2018) Competitive Landscape of the EU{\textquoteright}s Insulation Materials Industry for Energy-Efficient Buildings: Revised Edition, , Publications Office, Maastricht, The Netherlands; Kalhor, K., Emaminejad, N., Qualitative and Quantitative Optimization of Thermal Insulation Materials: Insights from the Market and Energy Codes (2020) J. Build. Eng, 30, p. 101275; Schiavoni, S., D′Alessandro, F., Bianchi, F., Asdrubali, F., Insulation Materials for the Building Sector: A Review and Comparative Analysis (2016) Renew. Sustain. Energy Rev, 62, pp. 988-1011; Michalak, J., Czernik, S., Marcinek, M., Micha{\l}owski, B., Environmental Burdens of External Thermal Insulation Systems. Expanded Polystyrene vs. Mineral Wool: Case Study from Poland (2020) Sustainability, 12; Torres-Rivas, A., Palumbo, M., Haddad, A., Cabeza, L.F., Jim{\'e}nez, L., Boer, D., Multi-Objective Optimisation of Bio-Based Thermal Insulation Materials in Building Envelopes Considering Condensation Risk (2018) Appl. Energy, 224, pp. 602-614; Celzard, A., Fierro, V., Amaral-Labat, G., Pizzi, A., Torero, J., Flammability Assessment of Tannin-Based Cellular Materials (2011) Polym. Degrad. Stab, 96, pp. 477-482; Chen, X., Xi, X., Pizzi, A., Fredon, E., Zhou, X., Li, J., Gerardin, C., Du, G., Preparation and Characterization of Condensed Tannin Non-Isocyanate Polyurethane (NIPU) Rigid Foams by Ambient Temperature Blowing (2020) Polymers, 12. , 32235495; Pizzi, A., Tannin-Based Biofoams{\textemdash}A Review (2019) J. Renew. Mater, 7, pp. 477-492; Delgado-S{\'a}nchez, C., Santiago-Medina, F., Fierro, V., Pizzi, A., Celzard, A., Optimisation of {\textquotedblleft}Green{\textquotedblright} Tannin-Furanic Foams for Thermal Insulation by Experimental Design (2018) Mater. Des, 139, pp. 7-15; Lacoste, C., Basso, M.C., Pizzi, A., Laborie, M.-P., Celzard, A., Fierro, V., Pine Tannin-Based Rigid Foams: Mechanical and Thermal Properties (2013) Ind. Crops Prod, 43, pp. 245-250; S{\'a}nchez-Mart{\'i}n, J., Beltr{\'a}n-Heredia, J., Delgado-Rega{\~n}a, A., Rodr{\'i}guez-Gonz{\'a}lez, M.A., Rubio-Alonso, F., Optimization of Tannin Rigid Foam as Adsorbents for Wastewater Treatment (2013) Ind. Crops Prod, 49, pp. 507-514; Lacoste, C., Basso, M.-C., Pizzi, A., Celzard, A., Ella Ebang, E., Gallon, N., Charrier, B., Pine (P. pinaster) and Quebracho (S. lorentzii) Tannin-Based Foams as Green Acoustic Absorbers (2015) Ind. Crops Prod, 67, pp. 70-73; Meikleham, N.E., Pizzi, A., Acid-and Alkali-Catalyzed Tannin-Based Rigid Foams (1994) J. Appl. Polym. Sci, 53, pp. 1547-1556; Tondi, G., Link, M., Oo, C.W., Petutschnigg, A., A Simple Approach to Distinguish Classic and Formaldehyde-Free Tannin Based Rigid Foams by ATR FT-IR (2015) J. Spectrosc, 2015, p. 902340; Basso, M.C., Li, X., Fierro, V., Pizzi, A., Giovando, S., Celzard, A., Green, Formaldehyde-Free, Foams for Thermal Insulation (2011) Adv. Mater. Lett, 2, pp. 378-382; Basso, M.C., Giovando, S., Pizzi, A., Celzard, A., Fierro, V., Tannin/Furanic Foams without Blowing Agents and Formaldehyde (2013) Ind. Crops Prod, 49, pp. 17-22; Li, X., Essawy, H.A., Pizzi, A., Delmotte, L., Rode, K., Le Nouen, D., Fierro, V., Celzard, A., Modification of Tannin Based Rigid Foams Using Oligomers of a Hyperbranched Poly(Amine-Ester) (2012) J. Polym. Res, 19, p. 21; Zhou, X., Li, B., Xu, Y., Essawy, H., Wu, Z., Du, G., Tannin-Furanic Resin Foam Reinforced with Cellulose Nanofibers (CNF) (2019) Ind. Crops Prod, 134, pp. 107-112; Li, X., Basso, M.C., Fierro, V., Pizzi, A., Celzard, A., Chemical Modification of Tannin/Furanic Rigid Foams by Isocyanates and Polyurethanes (2012) Maderas Cienc. Tecnol, 14, pp. 257-265; Chen, X., Li, J., Pizzi, A., Fredon, E., Gerardin, C., Zhou, X., Du, G., Tannin-Furanic Foams Modified by Soybean Protein Isolate (SPI) and Industrial Lignin Substituting Formaldehyde Addition (2021) Ind. Crops Prod, 168, p. 113607; Eckardt, J., Neubauer, J., Sepperer, T., Donato, S., Zanetti, M., Cefarin, N., Vaccari, L., Schnabel, T., Synthesis and Characterization of High-Performing Sulfur-Free Tannin Foams (2020) Polymers, 12; Santiago-Medina, F.J., Delgado-S{\'a}nchez, C., Basso, M.C., Pizzi, A., Fierro, V., Celzard, A., Mechanically Blown Wall-Projected Tannin-Based Foams (2018) Ind. Crops Prod, 113, pp. 316-323; Santiago-Medina, F.J., Tenorio-Alfonso, A., Delgado-S{\'a}nchez, C., Basso, M.C., Pizzi, A., Celzard, A., Fierro, V., Franco, J.M., Projectable Tannin Foams by Mechanical and Chemical Expansion (2018) Ind. Crops Prod, 120, pp. 90-96; Shirmohammadli, Y., Efhamisisi, D., Pizzi, A., Tannins as a Sustainable Raw Material for Green Chemistry: A Review (2018) Ind. Crops Prod, 126, pp. 316-332; Pizzi, A., Tannins: Prospectives and Actual Industrial Applications (2019) Biomolecules, 9. , 31387308; Arbenz, A., Av{\'e}rous, L., Chemical Modification of Tannins to Elaborate Aromatic Biobased Macromolecular Architectures (2015) Green Chem, 17, pp. 2626-2646; Basso, M.C., Lacoste, C., Pizzi, A., Fredon, E., Delmotte, L., MALDI-TOF and 13C NMR Analysis of Flexible Films and Lacquers Derived from Tannin (2014) Ind. Crops Prod, 61, pp. 352-360; Pizzi, A., Stephanou, A., A Comparative C13 NMR Study of Polyflavonoid Tannin Extracts for Phenolic Polycondensates (1993) J. Appl. Polym. Sci, 50, pp. 2105-2113; Pasch, H., Pizzi, A., Considerations on the Macromolecular Structure of Chestnut Ellagitannins by Matrix-Assisted Laser Desorption/Ionization-Time-of-Flight Mass Spectrometry (2002) J. Appl. Polym. Sci, 85, pp. 429-437; Spina, S., Zhou, X., Segovia, C., Pizzi, A., Romagnoli, M., Giovando, S., Pasch, H., Delmotte, L., Phenolic Resin Adhesives Based on Chestnut (Castanea sativa) Hydrolysable Tannins (2013) J. Adhes. Sci. Technol, 27, pp. 2103-2111; {\v C}op, M., Lacoste, C., Conradi, M., Laborie, M.-P., Pizzi, A., Sernek, M., The Effect of the Composition of Spruce and Pine Tannin-Based Foams on Their Physical, Morphological and Compression Properties (2015) Ind. Crops Prod, 74, pp. 158-164; Marie, Z., Nicolas, V., Celzard, A., Fierro, V., Experimental Investigation of the Physical Foaming of Tannin-Based Thermoset Foams (2019) Ind. Crops Prod, 138, p. 111424; Azadeh, E., Chen, X., Pizzi, A., G{\'e}rardin, C., G{\'e}rardin, P., Essawy, H., Self-Blowing Non-Isocyanate Polyurethane Foams Based on Hydrolysable Tannins (2022) J. Renew. Mater, 10, pp. 3217-3227; Lagel, M.C., Pizzi, A., Giovando, S., Celzard, A., Development and Characterisation of Phenolic Foams with Phenol-Formaldehyde-Chestnut Tannins Resin (2014) J. Renew. Mater, 2, pp. 220-229; Varila, T., Romar, H., Luukkonen, T., Lassi, U., Physical Activation and Characterization of Tannin-Based Foams Enforced with Boric Acid and Zinc Chloride (2019) AIMS Mater. Sci, 6, pp. 301-314; {\v C}op, M., Gospodari{\v c}, B., Kemppainen, K., Giovando, S., Laborie, M.-P., Pizzi, A., Sernek, M., Characterization of the Curing Process of Mixed Pine and Spruce Tannin-Based Foams by Different Methods (2015) Eur. Polym. J, 69, pp. 29-37; {\v C}op, M., Laborie, M.P., Pizzi, A., Sernek, M., Curing Characterisation of Spruce Tannin-Based Foams Using the Advanced Isoconversional Method (2014) BioResources, 9, pp. 4643-4655; Petkova, B., Tcholakova, S., Chenkova, M., Golemanov, K., Denkov, N., Thorley, D., Stoyanov, S., Foamability of Aqueous Solutions: Role of Surfactant Type and Concentration (2020) Adv. Colloid Interface Sci, 276, p. 102084; Politova, N., Tcholakova, S., Valkova, Z., Golemanov, K., Denkov, N.D., Self-Regulation of Foam Volume and Bubble Size during Foaming via Shear Mixing (2018) Colloids Surf. A Physicochem. Eng. Asp, 539, pp. 18-28; Hu, X., Cheng, W., Li, C., Wang, G., Lin, X., Liu, Z., Effects of Surfactants on the Mechanical Properties, Microstructure, and Flame Resistance of Phenol{\textendash}Urea{\textendash}Formaldehyde Foam (2016) Polym. Bull, 73, pp. 1-20; Jalalian, M., Jiang, Q., Coulon, A., Storb, M., Woodward, R., Bismarck, A., Mechanically Whipped Phenolic Froths as Versatile Templates for Manufacturing Phenolic and Carbon Foams (2019) Mater. Des, 168, p. 107658; Sepperer, T., {\v S}ket, P., Petutschnigg, A., H{\"u}sing, N., Tannin-Furanic Foams Formed by Mechanical Agitation: Influence of Surfactant and Ingredient Ratios (2021) Polymers, 13; Kothekar, S.C., Ware, A.M., Waghmare, J.T., Momin, S.A., Comparative Analysis of the Properties of Tween-20, Tween-60, Tween-80, Arlacel-60, and Arlacel-80 (2007) J. Dispers. Sci. Technol, 28, pp. 477-484; Ziarati, H.B., Fasihi, M., Omranpour, H., The Effect of Resin Formulation on the Cellular Morphology and Mechanical Properties of Phenolic Foams (2020) J. Appl. Polym. Sci, 137, p. 48331; Tondi, G., Link, M., Kolbitsch, C., Lesacher, R., Petutschnigg, A., Pilot Plant Up-Scaling of Tannin Foams (2016) Ind. Crops Prod, 79, pp. 211-218; Tondi, G., Zhao, W., Pizzi, A., Du, G., Fierro, V., Celzard, A., Tannin-Based Rigid Foams: A Survey of Chemical and Physical Properties (2009) Bioresour. Technol, 100, pp. 5162-5169; Tondi, G., Pizzi, A., Tannin-Based Rigid Foams: Characterization and Modification (2009) Ind. Crops Prod, 29, pp. 356-363; de Yuso, A.M., Lagel, M.C., Pizzi, A., Fierro, V., Celzard, A., Structure and Properties of Rigid Foams Derived from Quebracho Tannin (2014) Mater. Des, 63, pp. 208-212; Cesprini, E., {\v S}ket, P., Causin, V., Zanetti, M., Tondi, G., Development of Quebracho (Schinopsis balansae) Tannin-Based Thermoset Resins (2021) Polymers, 13; Kolbitsch, C., Link, M., Petutschnigg, A., Wieland, S., Tondi, G., Microwave Produced Tannin-Furanic Foams (2012) J. Mater. Sci. Res, 1, p. 84; Li, X., Nicollin, A., Pizzi, A., Zhou, X., Sauget, A., Delmotte, L., Natural Tannin{\textendash}Furanic Thermosetting Moulding Plastics (2013) RSC Adv, 3, p. 17732; (2007) Rigid Cellular Plastics: Determination of Compression Properties, , ISO International Standards, Geneva, Switzerland",

year = "2023",

month = mar,

day = "20",

doi = "10.3390/molecules28062799",

language = "English",

volume = "28",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "6",

}

TY - JOUR

T1 - Comparing Condensed and Hydrolysable Tannins for Mechanical Foaming of Furanic Foams: Synthesis and Characterization

AU - Eckardt, J.

AU - Sepperer, T.

AU - Cesprini, E.

AU - Šket, P.

AU - Tondi, G.

N1 - Cited By :4 Export Date: 14 December 2023 CODEN: MOLEF Correspondence Address: Tondi, G.; TESAF Department, Viale dell’Università 16, Italy; email: [email protected] Funding details: European Commission, EC Funding details: Ministero dell’Istruzione, dell’Università e della Ricerca, MIUR Funding details: Università degli Studi di Padova, UNIPD Funding text 1: The authors gratefully acknowledge the European Union and the Italian Ministry of University and Research for the support with the PhD PON project “Development of sustainable tannin-based bio-foams for the thermal insulation of buildings” as well as the LERH doctoral school, the TESAF department of the University of Padua for the support of the project BIRD 2021 and the CERIC-ERIC Consortium for access to solid state C-NMR experimental facilities. 13 References: Pavel, C., Blagoeva, D., (2018) Competitive Landscape of the EU’s Insulation Materials Industry for Energy-Efficient Buildings: Revised Edition, , Publications Office, Maastricht, The Netherlands; Kalhor, K., Emaminejad, N., Qualitative and Quantitative Optimization of Thermal Insulation Materials: Insights from the Market and Energy Codes (2020) J. Build. Eng, 30, p. 101275; Schiavoni, S., D′Alessandro, F., Bianchi, F., Asdrubali, F., Insulation Materials for the Building Sector: A Review and Comparative Analysis (2016) Renew. Sustain. Energy Rev, 62, pp. 988-1011; Michalak, J., Czernik, S., Marcinek, M., Michałowski, B., Environmental Burdens of External Thermal Insulation Systems. Expanded Polystyrene vs. Mineral Wool: Case Study from Poland (2020) Sustainability, 12; Torres-Rivas, A., Palumbo, M., Haddad, A., Cabeza, L.F., Jiménez, L., Boer, D., Multi-Objective Optimisation of Bio-Based Thermal Insulation Materials in Building Envelopes Considering Condensation Risk (2018) Appl. Energy, 224, pp. 602-614; Celzard, A., Fierro, V., Amaral-Labat, G., Pizzi, A., Torero, J., Flammability Assessment of Tannin-Based Cellular Materials (2011) Polym. Degrad. Stab, 96, pp. 477-482; Chen, X., Xi, X., Pizzi, A., Fredon, E., Zhou, X., Li, J., Gerardin, C., Du, G., Preparation and Characterization of Condensed Tannin Non-Isocyanate Polyurethane (NIPU) Rigid Foams by Ambient Temperature Blowing (2020) Polymers, 12. , 32235495; Pizzi, A., Tannin-Based Biofoams—A Review (2019) J. Renew. Mater, 7, pp. 477-492; Delgado-Sánchez, C., Santiago-Medina, F., Fierro, V., Pizzi, A., Celzard, A., Optimisation of “Green” Tannin-Furanic Foams for Thermal Insulation by Experimental Design (2018) Mater. Des, 139, pp. 7-15; Lacoste, C., Basso, M.C., Pizzi, A., Laborie, M.-P., Celzard, A., Fierro, V., Pine Tannin-Based Rigid Foams: Mechanical and Thermal Properties (2013) Ind. Crops Prod, 43, pp. 245-250; Sánchez-Martín, J., Beltrán-Heredia, J., Delgado-Regaña, A., Rodríguez-González, M.A., Rubio-Alonso, F., Optimization of Tannin Rigid Foam as Adsorbents for Wastewater Treatment (2013) Ind. Crops Prod, 49, pp. 507-514; Lacoste, C., Basso, M.-C., Pizzi, A., Celzard, A., Ella Ebang, E., Gallon, N., Charrier, B., Pine (P. pinaster) and Quebracho (S. lorentzii) Tannin-Based Foams as Green Acoustic Absorbers (2015) Ind. Crops Prod, 67, pp. 70-73; Meikleham, N.E., Pizzi, A., Acid-and Alkali-Catalyzed Tannin-Based Rigid Foams (1994) J. Appl. Polym. Sci, 53, pp. 1547-1556; Tondi, G., Link, M., Oo, C.W., Petutschnigg, A., A Simple Approach to Distinguish Classic and Formaldehyde-Free Tannin Based Rigid Foams by ATR FT-IR (2015) J. Spectrosc, 2015, p. 902340; Basso, M.C., Li, X., Fierro, V., Pizzi, A., Giovando, S., Celzard, A., Green, Formaldehyde-Free, Foams for Thermal Insulation (2011) Adv. Mater. Lett, 2, pp. 378-382; Basso, M.C., Giovando, S., Pizzi, A., Celzard, A., Fierro, V., Tannin/Furanic Foams without Blowing Agents and Formaldehyde (2013) Ind. Crops Prod, 49, pp. 17-22; Li, X., Essawy, H.A., Pizzi, A., Delmotte, L., Rode, K., Le Nouen, D., Fierro, V., Celzard, A., Modification of Tannin Based Rigid Foams Using Oligomers of a Hyperbranched Poly(Amine-Ester) (2012) J. Polym. Res, 19, p. 21; Zhou, X., Li, B., Xu, Y., Essawy, H., Wu, Z., Du, G., Tannin-Furanic Resin Foam Reinforced with Cellulose Nanofibers (CNF) (2019) Ind. Crops Prod, 134, pp. 107-112; Li, X., Basso, M.C., Fierro, V., Pizzi, A., Celzard, A., Chemical Modification of Tannin/Furanic Rigid Foams by Isocyanates and Polyurethanes (2012) Maderas Cienc. Tecnol, 14, pp. 257-265; Chen, X., Li, J., Pizzi, A., Fredon, E., Gerardin, C., Zhou, X., Du, G., Tannin-Furanic Foams Modified by Soybean Protein Isolate (SPI) and Industrial Lignin Substituting Formaldehyde Addition (2021) Ind. Crops Prod, 168, p. 113607; Eckardt, J., Neubauer, J., Sepperer, T., Donato, S., Zanetti, M., Cefarin, N., Vaccari, L., Schnabel, T., Synthesis and Characterization of High-Performing Sulfur-Free Tannin Foams (2020) Polymers, 12; Santiago-Medina, F.J., Delgado-Sánchez, C., Basso, M.C., Pizzi, A., Fierro, V., Celzard, A., Mechanically Blown Wall-Projected Tannin-Based Foams (2018) Ind. Crops Prod, 113, pp. 316-323; Santiago-Medina, F.J., Tenorio-Alfonso, A., Delgado-Sánchez, C., Basso, M.C., Pizzi, A., Celzard, A., Fierro, V., Franco, J.M., Projectable Tannin Foams by Mechanical and Chemical Expansion (2018) Ind. Crops Prod, 120, pp. 90-96; Shirmohammadli, Y., Efhamisisi, D., Pizzi, A., Tannins as a Sustainable Raw Material for Green Chemistry: A Review (2018) Ind. Crops Prod, 126, pp. 316-332; Pizzi, A., Tannins: Prospectives and Actual Industrial Applications (2019) Biomolecules, 9. , 31387308; Arbenz, A., Avérous, L., Chemical Modification of Tannins to Elaborate Aromatic Biobased Macromolecular Architectures (2015) Green Chem, 17, pp. 2626-2646; Basso, M.C., Lacoste, C., Pizzi, A., Fredon, E., Delmotte, L., MALDI-TOF and 13C NMR Analysis of Flexible Films and Lacquers Derived from Tannin (2014) Ind. Crops Prod, 61, pp. 352-360; Pizzi, A., Stephanou, A., A Comparative C13 NMR Study of Polyflavonoid Tannin Extracts for Phenolic Polycondensates (1993) J. Appl. Polym. Sci, 50, pp. 2105-2113; Pasch, H., Pizzi, A., Considerations on the Macromolecular Structure of Chestnut Ellagitannins by Matrix-Assisted Laser Desorption/Ionization-Time-of-Flight Mass Spectrometry (2002) J. Appl. Polym. Sci, 85, pp. 429-437; Spina, S., Zhou, X., Segovia, C., Pizzi, A., Romagnoli, M., Giovando, S., Pasch, H., Delmotte, L., Phenolic Resin Adhesives Based on Chestnut (Castanea sativa) Hydrolysable Tannins (2013) J. Adhes. Sci. Technol, 27, pp. 2103-2111; Čop, M., Lacoste, C., Conradi, M., Laborie, M.-P., Pizzi, A., Sernek, M., The Effect of the Composition of Spruce and Pine Tannin-Based Foams on Their Physical, Morphological and Compression Properties (2015) Ind. Crops Prod, 74, pp. 158-164; Marie, Z., Nicolas, V., Celzard, A., Fierro, V., Experimental Investigation of the Physical Foaming of Tannin-Based Thermoset Foams (2019) Ind. Crops Prod, 138, p. 111424; Azadeh, E., Chen, X., Pizzi, A., Gérardin, C., Gérardin, P., Essawy, H., Self-Blowing Non-Isocyanate Polyurethane Foams Based on Hydrolysable Tannins (2022) J. Renew. Mater, 10, pp. 3217-3227; Lagel, M.C., Pizzi, A., Giovando, S., Celzard, A., Development and Characterisation of Phenolic Foams with Phenol-Formaldehyde-Chestnut Tannins Resin (2014) J. Renew. Mater, 2, pp. 220-229; Varila, T., Romar, H., Luukkonen, T., Lassi, U., Physical Activation and Characterization of Tannin-Based Foams Enforced with Boric Acid and Zinc Chloride (2019) AIMS Mater. Sci, 6, pp. 301-314; Čop, M., Gospodarič, B., Kemppainen, K., Giovando, S., Laborie, M.-P., Pizzi, A., Sernek, M., Characterization of the Curing Process of Mixed Pine and Spruce Tannin-Based Foams by Different Methods (2015) Eur. Polym. J, 69, pp. 29-37; Čop, M., Laborie, M.P., Pizzi, A., Sernek, M., Curing Characterisation of Spruce Tannin-Based Foams Using the Advanced Isoconversional Method (2014) BioResources, 9, pp. 4643-4655; Petkova, B., Tcholakova, S., Chenkova, M., Golemanov, K., Denkov, N., Thorley, D., Stoyanov, S., Foamability of Aqueous Solutions: Role of Surfactant Type and Concentration (2020) Adv. Colloid Interface Sci, 276, p. 102084; Politova, N., Tcholakova, S., Valkova, Z., Golemanov, K., Denkov, N.D., Self-Regulation of Foam Volume and Bubble Size during Foaming via Shear Mixing (2018) Colloids Surf. A Physicochem. Eng. Asp, 539, pp. 18-28; Hu, X., Cheng, W., Li, C., Wang, G., Lin, X., Liu, Z., Effects of Surfactants on the Mechanical Properties, Microstructure, and Flame Resistance of Phenol–Urea–Formaldehyde Foam (2016) Polym. Bull, 73, pp. 1-20; Jalalian, M., Jiang, Q., Coulon, A., Storb, M., Woodward, R., Bismarck, A., Mechanically Whipped Phenolic Froths as Versatile Templates for Manufacturing Phenolic and Carbon Foams (2019) Mater. Des, 168, p. 107658; Sepperer, T., Šket, P., Petutschnigg, A., Hüsing, N., Tannin-Furanic Foams Formed by Mechanical Agitation: Influence of Surfactant and Ingredient Ratios (2021) Polymers, 13; Kothekar, S.C., Ware, A.M., Waghmare, J.T., Momin, S.A., Comparative Analysis of the Properties of Tween-20, Tween-60, Tween-80, Arlacel-60, and Arlacel-80 (2007) J. Dispers. Sci. Technol, 28, pp. 477-484; Ziarati, H.B., Fasihi, M., Omranpour, H., The Effect of Resin Formulation on the Cellular Morphology and Mechanical Properties of Phenolic Foams (2020) J. Appl. Polym. Sci, 137, p. 48331; Tondi, G., Link, M., Kolbitsch, C., Lesacher, R., Petutschnigg, A., Pilot Plant Up-Scaling of Tannin Foams (2016) Ind. Crops Prod, 79, pp. 211-218; Tondi, G., Zhao, W., Pizzi, A., Du, G., Fierro, V., Celzard, A., Tannin-Based Rigid Foams: A Survey of Chemical and Physical Properties (2009) Bioresour. Technol, 100, pp. 5162-5169; Tondi, G., Pizzi, A., Tannin-Based Rigid Foams: Characterization and Modification (2009) Ind. Crops Prod, 29, pp. 356-363; de Yuso, A.M., Lagel, M.C., Pizzi, A., Fierro, V., Celzard, A., Structure and Properties of Rigid Foams Derived from Quebracho Tannin (2014) Mater. Des, 63, pp. 208-212; Cesprini, E., Šket, P., Causin, V., Zanetti, M., Tondi, G., Development of Quebracho (Schinopsis balansae) Tannin-Based Thermoset Resins (2021) Polymers, 13; Kolbitsch, C., Link, M., Petutschnigg, A., Wieland, S., Tondi, G., Microwave Produced Tannin-Furanic Foams (2012) J. Mater. Sci. Res, 1, p. 84; Li, X., Nicollin, A., Pizzi, A., Zhou, X., Sauget, A., Delmotte, L., Natural Tannin–Furanic Thermosetting Moulding Plastics (2013) RSC Adv, 3, p. 17732; (2007) Rigid Cellular Plastics: Determination of Compression Properties, , ISO International Standards, Geneva, Switzerland

PY - 2023/3/20

Y1 - 2023/3/20

N2 - This study examined the potential of hydrolysable tannin in comparison to condensed tannins for the production of furanic foams. The results indicate that chestnut tannin presents lower reactivity and requires a stronger acid for the polymerization. Additionally, foamability and density were found to be dependent on both surfactant concentration and tannin type, allowing lower densities for mimosa tannin and lower thermal conductivities for chestnut-based foams. Mimosa tannin was found to have the highest compression strength, followed by quebracho and chestnut, promising thermal conductivity of around 50 mW/m·K for 300 kg/m3 foams, which suggests that chestnut foams have the potential to performing highly when the density is reduced. Chemical analysis revealed that the methylene moieties of the furanics are non-specific and produces new covalent bonds with nucleophilic substrates: -OH groups and free-positions in the flavonoids. Overall, this study opens new perspectives for the application of hydrolysable tannins in polymer and material science.

AB - This study examined the potential of hydrolysable tannin in comparison to condensed tannins for the production of furanic foams. The results indicate that chestnut tannin presents lower reactivity and requires a stronger acid for the polymerization. Additionally, foamability and density were found to be dependent on both surfactant concentration and tannin type, allowing lower densities for mimosa tannin and lower thermal conductivities for chestnut-based foams. Mimosa tannin was found to have the highest compression strength, followed by quebracho and chestnut, promising thermal conductivity of around 50 mW/m·K for 300 kg/m3 foams, which suggests that chestnut foams have the potential to performing highly when the density is reduced. Chemical analysis revealed that the methylene moieties of the furanics are non-specific and produces new covalent bonds with nucleophilic substrates: -OH groups and free-positions in the flavonoids. Overall, this study opens new perspectives for the application of hydrolysable tannins in polymer and material science.

KW - 13CNMR analysis

KW - ATR FT-IR

KW - bio-based materials

KW - bio-polymers

KW - insulation

KW - lightweight

KW - natural extracts

UR - https://www.mendeley.com/catalogue/9ca63fdf-bb3e-3a34-8db6-1101a00dbb2d/

U2 - 10.3390/molecules28062799

DO - 10.3390/molecules28062799

M3 - Article

C2 - 36985772

SN - 1420-3049

VL - 28

JO - Molecules

JF - Molecules

IS - 6

ER -

Comparing Condensed and Hydrolysable Tannins for Mechanical Foaming of Furanic Foams: Synthesis and Characterization

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