Bio-Based Tannin-Furanic-Silk Adhesives: Applications in Plywood and Chemical Cross-linking Mechanisms

E. Cesprini; J. Jorda; M. Paolantoni; L. Valentini; P. Šket; V. Causin; D.E. Bedolla; M. Zanetti; G. Tondi

doi:10.1021/acsapm.3c00539

Bio-Based Tannin-Furanic-Silk Adhesives: Applications in Plywood and Chemical Cross-linking Mechanisms

E. Cesprini
, J. Jorda
, M. Paolantoni
, L. Valentini
, P. Šket
, V. Causin
, D.E. Bedolla
, M. Zanetti
, G. Tondi

Design and Green Engineering

Department of Land, Environment, Agriculture and Forestry, University of Padua
Department of Chemistry, Biology and Biotechnology, University of Perugia
Civil and Environmental Engineering Department, University of Perugia
National Institute of Chemistry Ljubljana
Department of Chemical Sciences, University of Padua
Elettra-Sincrotrone Trieste S.C.p.A. di interesse nazionale
Area Science Park

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

Abstract

Wood polyphenolic extracts, commonly called tannins, are excellent candidates for the production of bioplastics due to their abundance in nature, their commercial availability, and their reactivity. In particular, they were tested as wood adhesives with several hardeners, but their low moisture resistance and their rigidity reduced their technological interest. In the present study, we combined regenerated silk (RS) with tannin-furanic formulations to improve their properties. Three-layer plywood glued with these several fully renewable tannin-silk-furanic adhesives were tested for their mechanical properties: the modulus of elasticity, the modulus of rupture, and both dry and wet shear strength were enhanced when 20 wt % of RS was added. Initially, the cross section of the prepared samples was investigated by scanning electron microscopy, indicating a good dispersion of RS within the tannin-furanic matrix. Afterward, thermomechanical analysis of the adhesive highlighted that RS slows down the polymerization rate, decreasing the cross-linking kinetics of polyfurfuryl alcohol. Chemical investigations through ATR-FTIR and 13C-NMR show the formation of covalent bonds between RS and the furanic matrix. In summary, the combination of bioresources from the vegetal and animal kingdom allows the manufacturing of fully bio-based adhesives with enhanced mechanical properties and water resistance. This represents an important breakthrough in the exploitation of polyphenols, opening perspectives for their application in material science.

Original language	English
Pages (from-to)	4468-4476
Number of pages	9
Journal	ACS Appl. Polymer Mat.
Volume	5
Issue number	6
DOIs	https://doi.org/10.1021/acsapm.3c00539
Publication status	Published - 16 May 2023

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

engineered wood products
fibroin
flavonoids
furanic
protein
regenerated silk
sustainable
Adhesives
Building materials
Composite materials
Crosslinking
Flavonoids
Plywood
Scanning electron microscopy
Silk
Adhesive applications
Bio-based
Chemical cross-linking
Engineered wood products
Fibroin
Flavonoid
Furanic
matrix
Regenerated silk
Sustainable
Tannins

Access to Document

10.1021/acsapm.3c00539

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85161088965&doi=10.1021%2facsapm.3c00539&partnerID=40&md5=198a48ce504626590cd95260ec1e3176

Cite this

@article{2ac518bf14e5465796228fc4ae9e5c0c,

title = "Bio-Based Tannin-Furanic-Silk Adhesives: Applications in Plywood and Chemical Cross-linking Mechanisms",

abstract = "Wood polyphenolic extracts, commonly called tannins, are excellent candidates for the production of bioplastics due to their abundance in nature, their commercial availability, and their reactivity. In particular, they were tested as wood adhesives with several hardeners, but their low moisture resistance and their rigidity reduced their technological interest. In the present study, we combined regenerated silk (RS) with tannin-furanic formulations to improve their properties. Three-layer plywood glued with these several fully renewable tannin-silk-furanic adhesives were tested for their mechanical properties: the modulus of elasticity, the modulus of rupture, and both dry and wet shear strength were enhanced when 20 wt \% of RS was added. Initially, the cross section of the prepared samples was investigated by scanning electron microscopy, indicating a good dispersion of RS within the tannin-furanic matrix. Afterward, thermomechanical analysis of the adhesive highlighted that RS slows down the polymerization rate, decreasing the cross-linking kinetics of polyfurfuryl alcohol. Chemical investigations through ATR-FTIR and 13C-NMR show the formation of covalent bonds between RS and the furanic matrix. In summary, the combination of bioresources from the vegetal and animal kingdom allows the manufacturing of fully bio-based adhesives with enhanced mechanical properties and water resistance. This represents an important breakthrough in the exploitation of polyphenols, opening perspectives for their application in material science.",

keywords = "engineered wood products, fibroin, flavonoids, furanic, protein, regenerated silk, sustainable, Adhesives, Building materials, Composite materials, Crosslinking, Flavonoids, Plywood, Scanning electron microscopy, Silk, Adhesive applications, Bio-based, Chemical cross-linking, Engineered wood products, Fibroin, Flavonoid, Furanic, matrix, Regenerated silk, Sustainable, Tannins",

author = "E. Cesprini and J. Jorda and M. Paolantoni and L. Valentini and P. {\v S}ket and V. Causin and D.E. Bedolla and M. Zanetti and G. Tondi",

note = "Cited By :1 Export Date: 14 December 2023 Correspondence Address: Tondi, G.; TESAF Land Environment Agriculture \& Forestry Department, Viale dell{\textquoteright}Universit{\`a} 16, Italy; email: [email protected] Funding details: Ministero dell{\textquoteright}Istruzione, dell{\textquoteright}Universit{\`a} e della Ricerca, MIUR, 2017FWC3WC, ITAT 1059 InCIMa4 Funding text 1: G.T. gratefully acknowledges the TESAF dept. for supporting this research with BIRD 2021 fundings {\textquotedblleft}Biocomby-{\textquotedblleft}. E.C. thanks the LERH doctorate school for the grant financing his PhD. L.V. received funding from the Italian Ministry of Education, University and Research (MIUR) under the PRIN project {\textquotedblleft}Development and promotion of the Levulinic acid and Carboxylate platforms by the formulation of advanced PHA-based biomaterials and their exploitation for 3D printed green-electronics applications{\textquotedblright} grant 2017FWC3WC. D.B. gratefully acknowledges the project Interreg ITAT 1059 InCIMa4 for supporting this study. References: S{\"o}derholm, P., The green economy transition: The challenges of technological change for sustainability (2020) Sustain. Earth, 3, p. 6; Plastic \& Climate: The hidden costs of a plastic planet (2019), https://www.ciel.org/wp-content/uploads/2019/05/Plastic-and-Climate-FINAL-2019.pdf; Zheng, J., Suh, S., Strategies to reduce the global carbon footprint of plastics (2019) Nat. Clim. Chang., 9, pp. 374-378; Spierling, S., Kn{\"u}pffer, E., Behnsen, H., Mudersbach, M., Krieg, H., Springer, S., Albrecht, S., Endres, H.J., Bio-Based Plastics - A review of environmental, social and cconomic impact assessments (2018) J. Clean. Prod., 185, pp. 476-491; Rosenboom, J.G., Langer, R., Traverso, G., The hidden costs of a plastic planet (2022) Nat. Rev. Mater., 7, pp. 117-137; Cesprini, E., De Iseppi, A., Giovando, S., Tarabra, E., Zanetti, M., {\v S}ket, P., Marangon, M., Tondi, G., Chemical characterization of cherry (Prunus Avium) extract in comparison with commercial mimosa and chestnut tannins (2022) Wood Sci. Technol., 56, pp. 1455-1473; 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; Falc{\~a}o, L., Ara{\'u}jo, M.E.M., Vegetable tannins used in the manufacture of historic leathers (2018) Molecules, 23, p. 1081; Cook, N.C., Samman, S., Flavonoids - chemistry, metabolism, cardioprotective effects, and dietary Sources (1996) J. Nutr. Biochem., 7, pp. 66-76; Eckardt, J., Neubauer, J., Sepperer, T., Donato, S., Zanetti, M., Cefarin, N., Vaccari, L., Tondi, G., Synthesis and characterization of high-performing sulfur-free tannin foams (2020) Polymers (Basel), 12, p. 564; Tondi, G., Pizzi, A., Tannin-based rigid foams: characterization and modification (2009) Ind. Crops Prod., 29, pp. 356-363; Arbenz, A., Av{\'e}rous, L., Chemical modification of tannins to elaborate aromatic biobased macromolecular architectures (2015) Green Chem., 17, pp. 2626-2646; Sommerauer, L., Thevenon, M.F., Petutschnigg, A., Tondi, G., Effect of hardening parameters of wood preservatives based on tannin copolymers (2019) Holzforschung, 73, pp. 457-467; Cesprini, E., Baccini, R., Urso, T., Zanetti, M., Tondi, G., Quebracho-based wood preservatives: effect of concentration and hardener on timber properties (2022) Coatings, 12, p. 568; Pizzi, A., Recent developments in eco-efficient bio-based adhesives for wood bonding: Opportunities and issues (2006) J. Adhes. Sci. Technol., 20, pp. 829-846; Hemmil{\"a}, V., Adamopoulos, S., Karlsson, O., Kumar, A., Development of sustainable bio-adhesives for engineered wood panels-A review (2017) RSC Adv., 7, pp. 38604-38630; Pizzi, A., Tannins: Prospectives and actual industrial applications (2019) Biomolecules, 9, p. 344; Tondi, G., Tannin-based copolymer resins: Synthesis and characterization by solid state 13C NMR and FT-IR spectroscopy (2017) Polymers (Basel), 9, p. 223; Gandini, A., Polymers from renewable resources: a challenge for the future of macromolecular materials (2008) Macromolecules, 41, pp. 9491-9504; Choura, M., Belgacem, N.M., Gandini, A., The acid-catalyzed polycondensation of furfuryl alcohol: old puzzles unravelled (1997) Macromol. Symp., 122, pp. 263-268; Choura, M., Belgacem, N.M., Gandini, A., Acid-catalyzed polycondensation of furfuryl alcohol: mechanisms of chromophore formation and cross-linking (1996) Macromolecules, 29, pp. 3839-3850; Pfriem, A., Dietrich, T., Buchelt, B., furfuryl alcohol impregnation for improved plasticization and fixation during the densification of wood (2012) Holzforschung, 66, pp. 215-218; Kong, L., Guan, H., Wang, X., In situ polymerization of furfuryl alcohol with ammonium dihydrogen phosphate in poplar wood for improved dimensional stability and flame retardancy (2018) ACS Sustainable Chem. Eng., 6, pp. 3349-3357; Yao, M., Yang, Y., Song, J., Yu, Y., Jin, Y., Lignin-based catalysts for chinese fir furfurylation to improve dimensional stability and mechanical properties (2017) Ind. Crops Prod., 107, pp. 38-44; Falco, G., Guigo, N., Vincent, L., Sbirrazzuoli, N., Opening furan for tailoring properties of bio-based poly(furfuryl alcohol) thermoset (2018) ChemSusChem, 11, pp. 1805-1812; Luckeneder, P., Gavino, J., Kuchernig, R., Petutschnigg, A., Tondi, G., Sustainable phenolic fractions as basis for furfuryl alcohol-based co-polymers and their use as wood adhesives (2016) Polymers (Basel), 8, p. 396; Szczurek, A., Fierro, V., Th{\'e}bault, M., Pizzi, A., Celzard, A., Structure and properties of poly(furfuryl alcohol)-tannin polyHIPEs (2016) Eur. Polym. J., 78, pp. 195-212; Cesprini, E., Causin, V., De Iseppi, A., Zanetti, M., Marangon, M., Barbu, M.C., Tondi, G., Renewable tannin-based adhesive from Quebracho extract and furfural for particleboards (2022) Forests, 13, p. 1781; Jorda, J., Cesprini, E., Barbu, M.-C., Tondi, G., Zanetti, M., Kr{\'a}l, P., Quebracho tannin bio-based adhesives for plywood (2022) Polymers (Basel), 14, p. 2257; Zhang, J., Long, C., Zhang, X., Liu, Z., Zhang, X., Liu, T., Li, J., Gao, Q., An easy-coating, versatile, and strong soy flour adhesive via a biomineralized structure combined with a biomimetic brush-like polymer (2022) Chem. Eng. J., 450; Xu, Y., Han, Y., Li, J., Luo, J., Shi, S.Q., Li, J., Gao, Q., Mao, A., Research progress of soybean protein adhesive: a review (2022) J. Renew. 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year = "2023",

month = may,

day = "16",

doi = "10.1021/acsapm.3c00539",

language = "English",

volume = "5",

pages = "4468--4476",

journal = "ACS Appl. Polymer Mat.",

issn = "2637-6105",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Bio-Based Tannin-Furanic-Silk Adhesives: Applications in Plywood and Chemical Cross-linking Mechanisms

AU - Cesprini, E.

AU - Jorda, J.

AU - Paolantoni, M.

AU - Valentini, L.

AU - Šket, P.

AU - Causin, V.

AU - Bedolla, D.E.

AU - Zanetti, M.

AU - Tondi, G.

N1 - Cited By :1 Export Date: 14 December 2023 Correspondence Address: Tondi, G.; TESAF Land Environment Agriculture & Forestry Department, Viale dell’Università 16, Italy; email: [email protected] Funding details: Ministero dell’Istruzione, dell’Università e della Ricerca, MIUR, 2017FWC3WC, ITAT 1059 InCIMa4 Funding text 1: G.T. gratefully acknowledges the TESAF dept. for supporting this research with BIRD 2021 fundings “Biocomby-“. E.C. thanks the LERH doctorate school for the grant financing his PhD. L.V. received funding from the Italian Ministry of Education, University and Research (MIUR) under the PRIN project “Development and promotion of the Levulinic acid and Carboxylate platforms by the formulation of advanced PHA-based biomaterials and their exploitation for 3D printed green-electronics applications” grant 2017FWC3WC. D.B. gratefully acknowledges the project Interreg ITAT 1059 InCIMa4 for supporting this study. References: Söderholm, P., The green economy transition: The challenges of technological change for sustainability (2020) Sustain. Earth, 3, p. 6; Plastic & Climate: The hidden costs of a plastic planet (2019), https://www.ciel.org/wp-content/uploads/2019/05/Plastic-and-Climate-FINAL-2019.pdf; Zheng, J., Suh, S., Strategies to reduce the global carbon footprint of plastics (2019) Nat. Clim. Chang., 9, pp. 374-378; Spierling, S., Knüpffer, E., Behnsen, H., Mudersbach, M., Krieg, H., Springer, S., Albrecht, S., Endres, H.J., Bio-Based Plastics - A review of environmental, social and cconomic impact assessments (2018) J. Clean. Prod., 185, pp. 476-491; Rosenboom, J.G., Langer, R., Traverso, G., The hidden costs of a plastic planet (2022) Nat. Rev. Mater., 7, pp. 117-137; Cesprini, E., De Iseppi, A., Giovando, S., Tarabra, E., Zanetti, M., Šket, P., Marangon, M., Tondi, G., Chemical characterization of cherry (Prunus Avium) extract in comparison with commercial mimosa and chestnut tannins (2022) Wood Sci. Technol., 56, pp. 1455-1473; 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; Falcão, L., Araújo, M.E.M., Vegetable tannins used in the manufacture of historic leathers (2018) Molecules, 23, p. 1081; Cook, N.C., Samman, S., Flavonoids - chemistry, metabolism, cardioprotective effects, and dietary Sources (1996) J. Nutr. Biochem., 7, pp. 66-76; Eckardt, J., Neubauer, J., Sepperer, T., Donato, S., Zanetti, M., Cefarin, N., Vaccari, L., Tondi, G., Synthesis and characterization of high-performing sulfur-free tannin foams (2020) Polymers (Basel), 12, p. 564; Tondi, G., Pizzi, A., Tannin-based rigid foams: characterization and modification (2009) Ind. Crops Prod., 29, pp. 356-363; Arbenz, A., Avérous, L., Chemical modification of tannins to elaborate aromatic biobased macromolecular architectures (2015) Green Chem., 17, pp. 2626-2646; Sommerauer, L., Thevenon, M.F., Petutschnigg, A., Tondi, G., Effect of hardening parameters of wood preservatives based on tannin copolymers (2019) Holzforschung, 73, pp. 457-467; Cesprini, E., Baccini, R., Urso, T., Zanetti, M., Tondi, G., Quebracho-based wood preservatives: effect of concentration and hardener on timber properties (2022) Coatings, 12, p. 568; Pizzi, A., Recent developments in eco-efficient bio-based adhesives for wood bonding: Opportunities and issues (2006) J. Adhes. Sci. Technol., 20, pp. 829-846; Hemmilä, V., Adamopoulos, S., Karlsson, O., Kumar, A., Development of sustainable bio-adhesives for engineered wood panels-A review (2017) RSC Adv., 7, pp. 38604-38630; Pizzi, A., Tannins: Prospectives and actual industrial applications (2019) Biomolecules, 9, p. 344; Tondi, G., Tannin-based copolymer resins: Synthesis and characterization by solid state 13C NMR and FT-IR spectroscopy (2017) Polymers (Basel), 9, p. 223; Gandini, A., Polymers from renewable resources: a challenge for the future of macromolecular materials (2008) Macromolecules, 41, pp. 9491-9504; Choura, M., Belgacem, N.M., Gandini, A., The acid-catalyzed polycondensation of furfuryl alcohol: old puzzles unravelled (1997) Macromol. Symp., 122, pp. 263-268; Choura, M., Belgacem, N.M., Gandini, A., Acid-catalyzed polycondensation of furfuryl alcohol: mechanisms of chromophore formation and cross-linking (1996) Macromolecules, 29, pp. 3839-3850; Pfriem, A., Dietrich, T., Buchelt, B., furfuryl alcohol impregnation for improved plasticization and fixation during the densification of wood (2012) Holzforschung, 66, pp. 215-218; Kong, L., Guan, H., Wang, X., In situ polymerization of furfuryl alcohol with ammonium dihydrogen phosphate in poplar wood for improved dimensional stability and flame retardancy (2018) ACS Sustainable Chem. Eng., 6, pp. 3349-3357; Yao, M., Yang, Y., Song, J., Yu, Y., Jin, Y., Lignin-based catalysts for chinese fir furfurylation to improve dimensional stability and mechanical properties (2017) Ind. Crops Prod., 107, pp. 38-44; Falco, G., Guigo, N., Vincent, L., Sbirrazzuoli, N., Opening furan for tailoring properties of bio-based poly(furfuryl alcohol) thermoset (2018) ChemSusChem, 11, pp. 1805-1812; Luckeneder, P., Gavino, J., Kuchernig, R., Petutschnigg, A., Tondi, G., Sustainable phenolic fractions as basis for furfuryl alcohol-based co-polymers and their use as wood adhesives (2016) Polymers (Basel), 8, p. 396; Szczurek, A., Fierro, V., Thébault, M., Pizzi, A., Celzard, A., Structure and properties of poly(furfuryl alcohol)-tannin polyHIPEs (2016) Eur. Polym. J., 78, pp. 195-212; Cesprini, E., Causin, V., De Iseppi, A., Zanetti, M., Marangon, M., Barbu, M.C., Tondi, G., Renewable tannin-based adhesive from Quebracho extract and furfural for particleboards (2022) Forests, 13, p. 1781; Jorda, J., Cesprini, E., Barbu, M.-C., Tondi, G., Zanetti, M., Král, P., Quebracho tannin bio-based adhesives for plywood (2022) Polymers (Basel), 14, p. 2257; Zhang, J., Long, C., Zhang, X., Liu, Z., Zhang, X., Liu, T., Li, J., Gao, Q., An easy-coating, versatile, and strong soy flour adhesive via a biomineralized structure combined with a biomimetic brush-like polymer (2022) Chem. Eng. J., 450; Xu, Y., Han, Y., Li, J., Luo, J., Shi, S.Q., Li, J., Gao, Q., Mao, A., Research progress of soybean protein adhesive: a review (2022) J. Renew. 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PY - 2023/5/16

Y1 - 2023/5/16

N2 - Wood polyphenolic extracts, commonly called tannins, are excellent candidates for the production of bioplastics due to their abundance in nature, their commercial availability, and their reactivity. In particular, they were tested as wood adhesives with several hardeners, but their low moisture resistance and their rigidity reduced their technological interest. In the present study, we combined regenerated silk (RS) with tannin-furanic formulations to improve their properties. Three-layer plywood glued with these several fully renewable tannin-silk-furanic adhesives were tested for their mechanical properties: the modulus of elasticity, the modulus of rupture, and both dry and wet shear strength were enhanced when 20 wt % of RS was added. Initially, the cross section of the prepared samples was investigated by scanning electron microscopy, indicating a good dispersion of RS within the tannin-furanic matrix. Afterward, thermomechanical analysis of the adhesive highlighted that RS slows down the polymerization rate, decreasing the cross-linking kinetics of polyfurfuryl alcohol. Chemical investigations through ATR-FTIR and 13C-NMR show the formation of covalent bonds between RS and the furanic matrix. In summary, the combination of bioresources from the vegetal and animal kingdom allows the manufacturing of fully bio-based adhesives with enhanced mechanical properties and water resistance. This represents an important breakthrough in the exploitation of polyphenols, opening perspectives for their application in material science.

AB - Wood polyphenolic extracts, commonly called tannins, are excellent candidates for the production of bioplastics due to their abundance in nature, their commercial availability, and their reactivity. In particular, they were tested as wood adhesives with several hardeners, but their low moisture resistance and their rigidity reduced their technological interest. In the present study, we combined regenerated silk (RS) with tannin-furanic formulations to improve their properties. Three-layer plywood glued with these several fully renewable tannin-silk-furanic adhesives were tested for their mechanical properties: the modulus of elasticity, the modulus of rupture, and both dry and wet shear strength were enhanced when 20 wt % of RS was added. Initially, the cross section of the prepared samples was investigated by scanning electron microscopy, indicating a good dispersion of RS within the tannin-furanic matrix. Afterward, thermomechanical analysis of the adhesive highlighted that RS slows down the polymerization rate, decreasing the cross-linking kinetics of polyfurfuryl alcohol. Chemical investigations through ATR-FTIR and 13C-NMR show the formation of covalent bonds between RS and the furanic matrix. In summary, the combination of bioresources from the vegetal and animal kingdom allows the manufacturing of fully bio-based adhesives with enhanced mechanical properties and water resistance. This represents an important breakthrough in the exploitation of polyphenols, opening perspectives for their application in material science.

KW - engineered wood products

KW - fibroin

KW - flavonoids

KW - furanic

KW - protein

KW - regenerated silk

KW - sustainable

KW - Adhesives

KW - Building materials

KW - Composite materials

KW - Crosslinking

KW - Flavonoids

KW - Plywood

KW - Scanning electron microscopy

KW - Silk

KW - Adhesive applications

KW - Bio-based

KW - Chemical cross-linking

KW - Engineered wood products

KW - Fibroin

KW - Flavonoid

KW - Furanic

KW - matrix

KW - Regenerated silk

KW - Sustainable

KW - Tannins

UR - https://www.mendeley.com/catalogue/bfc2b4a9-5f1b-3b26-aec3-3fd03c400494/

U2 - 10.1021/acsapm.3c00539

DO - 10.1021/acsapm.3c00539

M3 - Article

SN - 2637-6105

VL - 5

SP - 4468

EP - 4476

JO - ACS Appl. Polymer Mat.

JF - ACS Appl. Polymer Mat.

IS - 6

ER -

Bio-Based Tannin-Furanic-Silk Adhesives: Applications in Plywood and Chemical Cross-linking Mechanisms

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