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Published in: Wood Science and Technology 4/2019

28-05-2019 | Original

A sustainable bio-based adhesive derived from defatted soy flour and epichlorohydrin

Authors: Nairong Chen, Qiaojia Lin, Peitao Zheng, Jiuping Rao, Qinzhi Zeng, Jianping Sun

Published in: Wood Science and Technology | Issue 4/2019

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Abstract

This study reports on the preparation and application of bio-based adhesive derived from renewable defatted soy flour (DSF) and epichlorohydrin (ECH), aiming at substituting formaldehyde-based adhesives in the wood industry. DSF was treated with Viscozyme® L to hydrolyze plant cell wall carbohydrates and then adjusted to an extremely low pH with hydrochloric acid containing ferric chloride to unfold the tertiary and/or quaternary structure of soy protein and expose its functional groups. The treated DSF was then glycidized with ECH to obtain the bio-based adhesive. The resulting adhesive contained epoxy groups, which were evidenced by Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and 1H nuclear magnetic resonance. After curing, the epoxy groups contributed to good thermal stability and gluability of the adhesive. The grafting ratio of ECH decreased by 37.8% as the mass fraction added was increased from 5 to 25%, whereas the viscosity increased sharply by 2889.5% and the solid content increased slowly by 10.5%. Wet shear strength of Pinus massoniana plywood bonded with the bio-based adhesive with an ECH mass fraction of > 10% of the DSF mass was higher than 0.93 MPa, which met the requirements of the Chinese National Standard for plywood for interior/exterior applications. These results support the use of soy flour-based adhesives for plywood and provide data for evaluating their use as sustainable materials for other applications.

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Literature
go back to reference Almena A, Martín M (2016) Technoeconomic analysis of the production of epichlorohydrin from glycerol. Ind Eng Chem Res 55:3226–3238CrossRef Almena A, Martín M (2016) Technoeconomic analysis of the production of epichlorohydrin from glycerol. Ind Eng Chem Res 55:3226–3238CrossRef
go back to reference Amaral-Labat G, Pizzi A, Goncalves A, Celzard A, Rigolet S, Rocha G (2008) Environment-friendly soy flour-based resins without formaldehyde. J Appl Polym Sci 108:624–632CrossRef Amaral-Labat G, Pizzi A, Goncalves A, Celzard A, Rigolet S, Rocha G (2008) Environment-friendly soy flour-based resins without formaldehyde. J Appl Polym Sci 108:624–632CrossRef
go back to reference Auvergne R, Caillol S, David G, Boutevin B, Pascault J-P (2013) Biobased thermosetting epoxy: present and future. Chem Rev 114:1082–1115CrossRefPubMed Auvergne R, Caillol S, David G, Boutevin B, Pascault J-P (2013) Biobased thermosetting epoxy: present and future. Chem Rev 114:1082–1115CrossRefPubMed
go back to reference Bergaoui M, Aguir C, Khalfaoui M, Enciso E, Duclaux L, Reinert L, Fierro JLG (2017) New insights in the adsorption of Bovine Serum Albumin onto carbon nanoparticles derived from organic resin: experimental and theoretical studies. Microporous Mesoporous Mater 241:418–428CrossRef Bergaoui M, Aguir C, Khalfaoui M, Enciso E, Duclaux L, Reinert L, Fierro JLG (2017) New insights in the adsorption of Bovine Serum Albumin onto carbon nanoparticles derived from organic resin: experimental and theoretical studies. Microporous Mesoporous Mater 241:418–428CrossRef
go back to reference Chen N, Lin Q, Rao J, Zeng Q (2013) Water resistances and bonding strengths of soy-based adhesives containing different carbohydrates. Ind Crop Prod 50:44–49CrossRef Chen N, Lin Q, Rao J, Zeng Q (2013) Water resistances and bonding strengths of soy-based adhesives containing different carbohydrates. Ind Crop Prod 50:44–49CrossRef
go back to reference Chen N, Zeng Q, Rao J, Lin Q (2014) Effect of preparation conditions on bonding strength of soy-based adhesives via viscozyme L action on soy flour slurry. BioResources 9:7444–7453 Chen N, Zeng Q, Rao J, Lin Q (2014) Effect of preparation conditions on bonding strength of soy-based adhesives via viscozyme L action on soy flour slurry. BioResources 9:7444–7453
go back to reference Chen N, Huang J, Li K (2019) Investigation of a new formaldehyde-free adhesive consisting of soybean flour and Kymene® 736 for interior plywood. Holzforschung 73:409–414CrossRef Chen N, Huang J, Li K (2019) Investigation of a new formaldehyde-free adhesive consisting of soybean flour and Kymene® 736 for interior plywood. Holzforschung 73:409–414CrossRef
go back to reference Cheng E, Sun X, Karr GS (2004) Adhesive properties of modified soybean flour in wheat straw particleboard. Compos A 35:297–302CrossRef Cheng E, Sun X, Karr GS (2004) Adhesive properties of modified soybean flour in wheat straw particleboard. Compos A 35:297–302CrossRef
go back to reference Chu JH, Kwak J, Kim S-D et al (2014) Monolithic graphene oxide sheets with controllable composition. Nat Commun 5:3383CrossRefPubMed Chu JH, Kwak J, Kim S-D et al (2014) Monolithic graphene oxide sheets with controllable composition. Nat Commun 5:3383CrossRefPubMed
go back to reference Enterria M, Martin-Jimeno FJ, Suarez-Garcia F et al (2016) Effect of nanostructure on the supercapacitor performance of activated carbon xerogels obtained from hydrothermally carbonized glucose-graphene oxide hybrids. Carbon 105:474–483CrossRef Enterria M, Martin-Jimeno FJ, Suarez-Garcia F et al (2016) Effect of nanostructure on the supercapacitor performance of activated carbon xerogels obtained from hydrothermally carbonized glucose-graphene oxide hybrids. Carbon 105:474–483CrossRef
go back to reference Fache M, Montérémal C, Boutevin B, Caillol S (2015) Amine hardeners and epoxy cross-linker from aromatic renewable resources. Eur Polym J 73:344–362CrossRef Fache M, Montérémal C, Boutevin B, Caillol S (2015) Amine hardeners and epoxy cross-linker from aromatic renewable resources. Eur Polym J 73:344–362CrossRef
go back to reference Forrest T, Rabine JP, Rouillard M (2011) Organic spectroscopy workbook. Wiley, New York Forrest T, Rabine JP, Rouillard M (2011) Organic spectroscopy workbook. Wiley, New York
go back to reference Fourcade D, Ritter BS, Walter P, Schönfeld R, Mülhaupt R (2013) Renewable resource-based epoxy resins derived from multifunctional poly (4-hydroxybenzoates). Green Chem 15:910–918CrossRef Fourcade D, Ritter BS, Walter P, Schönfeld R, Mülhaupt R (2013) Renewable resource-based epoxy resins derived from multifunctional poly (4-hydroxybenzoates). Green Chem 15:910–918CrossRef
go back to reference Friedman M (2003) Chemistry, biochemistry, and safety of acrylamide: a review. J Agric Food Chem 51:4504–4526CrossRefPubMed Friedman M (2003) Chemistry, biochemistry, and safety of acrylamide: a review. J Agric Food Chem 51:4504–4526CrossRefPubMed
go back to reference Frihart CR, Satori H (2013) Soy flour dispersibility and performance as wood adhesive. J Adhes Sci Technol 27:2043–2052CrossRef Frihart CR, Satori H (2013) Soy flour dispersibility and performance as wood adhesive. J Adhes Sci Technol 27:2043–2052CrossRef
go back to reference Gadwal I, Khan A (2013) Protecting-group-free synthesis of chain-end multifunctional polymers by combining ATRP with thiol-epoxy ‘click’ chemistry. Polym Chem 4:2440–2444CrossRef Gadwal I, Khan A (2013) Protecting-group-free synthesis of chain-end multifunctional polymers by combining ATRP with thiol-epoxy ‘click’ chemistry. Polym Chem 4:2440–2444CrossRef
go back to reference Gardner SD, Singamsetty CS, Booth GL, He G-R, Pittman CU (1995) Surface characterization of carbon fibers using angle-resolved XPS and ISS. Carbon 33:587–595CrossRef Gardner SD, Singamsetty CS, Booth GL, He G-R, Pittman CU (1995) Surface characterization of carbon fibers using angle-resolved XPS and ISS. Carbon 33:587–595CrossRef
go back to reference Ghahri S, Pizzi A (2018) Improving soy-based adhesives for wood particleboard by tannins addition. Wood Sci Technol 52:261–279CrossRef Ghahri S, Pizzi A (2018) Improving soy-based adhesives for wood particleboard by tannins addition. Wood Sci Technol 52:261–279CrossRef
go back to reference Gu J (2015) Present situation and development trend of wood adhesives in China. Adhesion 36:28–31 Gu J (2015) Present situation and development trend of wood adhesives in China. Adhesion 36:28–31
go back to reference Gu K, Li K (2011) Preparation and evaluation of particleboard with a soy flour-polyethylenimine-maleic anhydride adhesive. J Am Oil Chem Soc 88:673–679CrossRef Gu K, Li K (2011) Preparation and evaluation of particleboard with a soy flour-polyethylenimine-maleic anhydride adhesive. J Am Oil Chem Soc 88:673–679CrossRef
go back to reference Kim DH, Na SK, Park JS, Yoon KJ, Ihm DW (2002) Studies on the preparation of hydrolyzed starch-g-PAN (HSPAN)/PVA blend films: effect of the reaction with epichlorohydrin. Eur Polym J 38:1199–1204CrossRef Kim DH, Na SK, Park JS, Yoon KJ, Ihm DW (2002) Studies on the preparation of hydrolyzed starch-g-PAN (HSPAN)/PVA blend films: effect of the reaction with epichlorohydrin. Eur Polym J 38:1199–1204CrossRef
go back to reference Koronis G, Silva A, Fontul M (2013) Green composites: a review of adequate materials for automotive applications. Compos Part B 44:120–127CrossRef Koronis G, Silva A, Fontul M (2013) Green composites: a review of adequate materials for automotive applications. Compos Part B 44:120–127CrossRef
go back to reference Li H, Kang H, Zhang W, Zhang S, Li J (2016) Physicochemical properties of modified soybean-flour adhesives enhanced by carboxylated styrene-butadiene rubber latex. Int J Adhes Adhes 66:59–64CrossRef Li H, Kang H, Zhang W, Zhang S, Li J (2016) Physicochemical properties of modified soybean-flour adhesives enhanced by carboxylated styrene-butadiene rubber latex. Int J Adhes Adhes 66:59–64CrossRef
go back to reference Lu Q, Wu C, Liu D et al (2017) A facile and simple method for synthesis of graphene oxide quantum dots from black carbon. Green Chem 19:900–904CrossRef Lu Q, Wu C, Liu D et al (2017) A facile and simple method for synthesis of graphene oxide quantum dots from black carbon. Green Chem 19:900–904CrossRef
go back to reference Luo J, Li C, Li X, Luo J, Gao Q, Li J (2015) A new soybean meal-based bioadhesive enhanced with 5, 5-dimethyl hydantoin polyepoxide for the improved water resistance of plywood. RSC Adv 5:62957–62965CrossRef Luo J, Li C, Li X, Luo J, Gao Q, Li J (2015) A new soybean meal-based bioadhesive enhanced with 5, 5-dimethyl hydantoin polyepoxide for the improved water resistance of plywood. RSC Adv 5:62957–62965CrossRef
go back to reference Luo J, Luo J, Li X, Li K, Gao Q, Li J (2016) Toughening improvement to a soybean meal-based bioadhesive using an interpenetrating acrylic emulsion network. J Mater Sci 51:9330–9341CrossRef Luo J, Luo J, Li X, Li K, Gao Q, Li J (2016) Toughening improvement to a soybean meal-based bioadhesive using an interpenetrating acrylic emulsion network. J Mater Sci 51:9330–9341CrossRef
go back to reference McMurry J (2011) Organic chemistry. Brooks/Cole, Monterey McMurry J (2011) Organic chemistry. Brooks/Cole, Monterey
go back to reference Meier MA, Metzger JO, Schubert US (2007) Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 36:1788–1802CrossRefPubMed Meier MA, Metzger JO, Schubert US (2007) Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 36:1788–1802CrossRefPubMed
go back to reference Morin-Crini N, Crini G (2013) Environmental applications of water-insoluble β-cyclodextrin–epichlorohydrin polymers. Prog Polym Sci 38:344–368CrossRef Morin-Crini N, Crini G (2013) Environmental applications of water-insoluble β-cyclodextrin–epichlorohydrin polymers. Prog Polym Sci 38:344–368CrossRef
go back to reference Mottram DS, Wedzicha BL, Dodson AT (2002) Food chemistry: acrylamide is formed in the Maillard reaction. Nature 419:448–449CrossRefPubMed Mottram DS, Wedzicha BL, Dodson AT (2002) Food chemistry: acrylamide is formed in the Maillard reaction. Nature 419:448–449CrossRefPubMed
go back to reference NgaiáSum Y (2013) Synthesis of cyclic carbonates with carbon dioxide and cesium carbonate. Green Chem 15:2086–2090CrossRef NgaiáSum Y (2013) Synthesis of cyclic carbonates with carbon dioxide and cesium carbonate. Green Chem 15:2086–2090CrossRef
go back to reference Nielsen GD, Larsen ST, Wolkoff P (2017) Re-evaluation of the WHO (2010) formaldehyde indoor air quality guideline for cancer risk assessment. Arch Toxicol 91:35–61CrossRefPubMed Nielsen GD, Larsen ST, Wolkoff P (2017) Re-evaluation of the WHO (2010) formaldehyde indoor air quality guideline for cancer risk assessment. Arch Toxicol 91:35–61CrossRefPubMed
go back to reference Ning YC, Ernst RR (2005) Structural identification of organic compounds with spectroscopic techniques. Wiley, New York Ning YC, Ernst RR (2005) Structural identification of organic compounds with spectroscopic techniques. Wiley, New York
go back to reference Ning YC, Ernst RR (2011) Interpretation of organic spectra. Wiley, New YorkCrossRef Ning YC, Ernst RR (2011) Interpretation of organic spectra. Wiley, New YorkCrossRef
go back to reference Othmer K (1993) Encyclopedia of chemical technology, chlorocarbons and chlorohydrocarbons-CSUB 2/SUB to combustion technology. Wiley, New York Othmer K (1993) Encyclopedia of chemical technology, chlorocarbons and chlorohydrocarbons-CSUB 2/SUB to combustion technology. Wiley, New York
go back to reference Santacesaria E, Tesser R, Di Serio M, Casale L, Verde D (2009) New process for producing epichlorohydrin via glycerol chlorination. Ind Eng Chem Res 49:964–970CrossRef Santacesaria E, Tesser R, Di Serio M, Casale L, Verde D (2009) New process for producing epichlorohydrin via glycerol chlorination. Ind Eng Chem Res 49:964–970CrossRef
go back to reference Thakur VK, Kessler MR (2014) Synthesis and characterization of AN-g-SOY for sustainable polymer composites. ACS Sustain Chem Eng 2:2454–2460CrossRef Thakur VK, Kessler MR (2014) Synthesis and characterization of AN-g-SOY for sustainable polymer composites. ACS Sustain Chem Eng 2:2454–2460CrossRef
go back to reference Vázquez G, González-Álvarez J, López-Suevos F, Antorrena G (2003) Effect of veneer side wettability on bonding quality of Eucalyptus globulus plywoods prepared using a tannin–phenol–formaldehyde adhesive. Bioresour Technol 87:349–353CrossRefPubMed Vázquez G, González-Álvarez J, López-Suevos F, Antorrena G (2003) Effect of veneer side wettability on bonding quality of Eucalyptus globulus plywoods prepared using a tannin–phenol–formaldehyde adhesive. Bioresour Technol 87:349–353CrossRefPubMed
go back to reference Wu S (1987) Chain entanglement and melt viscosity of compatible polymer blends: poly (methyl methacrylate) and poly (styrene-acrylonitrile). Polymer 28:1144–1148CrossRef Wu S (1987) Chain entanglement and melt viscosity of compatible polymer blends: poly (methyl methacrylate) and poly (styrene-acrylonitrile). Polymer 28:1144–1148CrossRef
go back to reference Xu Y, Xu Y, Zhu W, Zhang W, Gao Q, Li J (2018) Improve the performance of soy protein-based adhesives by a polyurethane elastomer. Polymers 10:1016CrossRefPubMedCentral Xu Y, Xu Y, Zhu W, Zhang W, Gao Q, Li J (2018) Improve the performance of soy protein-based adhesives by a polyurethane elastomer. Polymers 10:1016CrossRefPubMedCentral
go back to reference Zhang Y, Zhang M, Chen M, Luo J, Li X, Gao Q, Li J (2018) Preparation and characterization of a soy protein-based high-performance adhesive with a hyperbranched cross-linked structure. Chem Eng J 354:1032–1041CrossRef Zhang Y, Zhang M, Chen M, Luo J, Li X, Gao Q, Li J (2018) Preparation and characterization of a soy protein-based high-performance adhesive with a hyperbranched cross-linked structure. Chem Eng J 354:1032–1041CrossRef
go back to reference Zheng P, Chen N, Mahfuzul Islam SM et al (2019) Development of self-crosslinked soy adhesive by enzyme complex from Aspergillus niger for production of all-biomass composite materials. ACS Sustain Chem Eng 7:3909–3916CrossRef Zheng P, Chen N, Mahfuzul Islam SM et al (2019) Development of self-crosslinked soy adhesive by enzyme complex from Aspergillus niger for production of all-biomass composite materials. ACS Sustain Chem Eng 7:3909–3916CrossRef
go back to reference Zhu D, Damodaran S (2014) Chemical phosphorylation improves the moisture resistance of soy flour-based wood adhesive. J Appl Polym Sci 131:40451 Zhu D, Damodaran S (2014) Chemical phosphorylation improves the moisture resistance of soy flour-based wood adhesive. J Appl Polym Sci 131:40451
Metadata
Title
A sustainable bio-based adhesive derived from defatted soy flour and epichlorohydrin
Authors
Nairong Chen
Qiaojia Lin
Peitao Zheng
Jiuping Rao
Qinzhi Zeng
Jianping Sun
Publication date
28-05-2019
Publisher
Springer Berlin Heidelberg
Published in
Wood Science and Technology / Issue 4/2019
Print ISSN: 0043-7719
Electronic ISSN: 1432-5225
DOI
https://doi.org/10.1007/s00226-019-01102-2

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