Exploring the formaldehyde reactivity of tannins with different molecular weight distributions: bayberry tannins and larch tannins
-
Tao Yang
Tao YangCollege of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, ChinaSearch for this author in:Mengqi DongCollege of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, ChinaSearch for this author in:Juqing CuiCollege of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, ChinaSearch for this author in:Lu GanCollege of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, ChinaSearch for this author in:Shuguang HanCollege of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, ChinaSearch for this author in:
Abstract
In recent years, tannin degradation has been used to obtain tannin materials with an optimal molecular weight distribution (MWD) for synthesizing tannin-formaldehyde (TF) resin with high performance, but the optimal MWD of tannins is still unknown. The excellent formaldehyde reactivity of tannins is the basis for the synthesis of high-performance TF resin. Based on the formaldehyde reactivity of tannins, bayberry tannins and larch tannins were used to explore the optimal MWD of tannins for TF resin synthesis. Progressive solvent precipitation (PSP) was used to obtain tannin fractions with different MWDs. The formaldehyde reactivity of tannins was determined using the modified Stiansy method combined with the standard curve method (GB/T 17657-2013). The bayberry tannin fraction [weight-average molecular weight (Mw) of acetylated tannin: 4115, mean degree of polymerization (mDP): 6.64] and the larch tannin fraction (Mw of acetylated tannin: 3906, mDP: 5.84) had the best formaldehyde reactivity. Furthermore, significant differences in the formaldehyde reactivity of condensed tannins (CTs) with different MWDs were observed. The obtained results can be used to purposefully degrade tannins to achieve an optimal MWD, which is beneficial for the production of TF adhesives with high performance.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This project was supported by a grant from the National Natural Science Foundation of China (grant number 31470590).
Employment or leadership: None declared.
Honorarium: None declared.
References
Arbenz, A., Averous, L. (2015) Chemical modification of tannins to elaborate aromatic biobased macromolecular architectures. Green Chem. 17:2626–2646.10.1039/C5GC00282FSearch in Google Scholar
Barbosa, A.P., Mano, E.B., Andrade, C.T. (2000) Tannin-based resins modified to reduce wood adhesive brittleness. Forest Prod. J. 50:89–92.Search in Google Scholar
Cadahía, E., Conde, E., García-Vallejo, M.C., Simón, B.F.D. (1996) Gel permeation chromatographic study of the molecular weight distribution of tannins in the wood, bark and leaves of Eucalyptus spp. Chromatographia 42:95–100.10.1007/BF02271062Search in Google Scholar
Can, M., Bulut, E., Ozacar, M. (2012) Synthesis and characterization of gallic acid resin and its interaction with palladium(II), rhodium(III) chloro complexes. Ind. Eng. Chem. Res. 51: 6052–6063.10.1021/ie300437uSearch in Google Scholar
Chai, W.M., Huang, Q., Lin, M.Z., Ou-Yang, C., Huang, W.Y., Wang, Y.X., Xu, K.L., Feng, H.L. (2018) Condensed tannins from longan bark as inhibitor of tyrosinase: structure, activity, and mechanism. J. Agr. Food Chem. 66:908–917.10.1021/acs.jafc.7b05481Search in Google Scholar PubMed
Fan, D.B., Chu, F.X., Qin, T.F., Li, J.Z. (2011) Effect of synthesis conditions on the structure and curing characteristics of high-urea content PUF resin. J Adhesion 87:1191–1203.10.1080/00218464.2011.628871Search in Google Scholar
Gao, Z.H., Yuan, J.L. (2007) Phenolated larch-bark formaldehyde adhesive with multiple additions of sodium hydroxide. Pigm. Resin. Technol. 36:279–285.10.1108/03699420710820388Search in Google Scholar
Gu, L.W., Kelm, M., Hammerstone, J.F., Beecher, G., Cunningham, D., Vannozzi, S., Prior, R.L. (2002) Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. J. Agr. Food Chem. 50:4852–4860.10.1021/jf020214vSearch in Google Scholar PubMed
Hemmila, V., Adamopoulos, S., Karlsson, O., Kumar, A. (2017) Development of sustainable bio-adhesives for engineered wood panels – a review. RSC Adv. 7:38604–38630.10.1039/C7RA06598ASearch in Google Scholar
Jahanshaei, S., Tabarsa, T., Asghari, J. (2012) Eco-friendly tannin-phenol formaldehyde resin for producing wood composites. Pigm. Resin. Technol. 41:296–301.10.1108/03699421211264857Search in Google Scholar
Kennedy, J.A., Jones, G.P. (2001) Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J. Agr. Food Chem. 49:1740–1746.10.1021/jf001030oSearch in Google Scholar PubMed
Köhler, N., Wray, V., Winterhalter, P. (2008) Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography. J. Chromatogr. A 1177:114–125.10.1016/j.chroma.2007.11.028Search in Google Scholar PubMed
Konai, N., Pizzi, A., Raidandi, D., Lagel, M.C., L’Hostis, C., Saidou, C., Hamido, A., Abdalla, S., Bahabri, F., Ganash, A. (2015) Aningre (Aningeria spp.) tannin extract characterization and performance as an adhesive resin. Ind. Crop. Prod. 77:225–231.10.1016/j.indcrop.2015.08.053Search in Google Scholar
Labarbe, B., Cheynier, V., Brossaud, F., Jeanmarc Souquet, A., Moutounet, M. (1999) Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization. J. Agr. Food Chem. 47:2719–2723.10.1021/jf990029qSearch in Google Scholar PubMed
Li, C.M., Leverence, R., Trombley, J.D., Xu, S.F., Yang, J., Tian, Y., Reed, J.D., Hagerman, A.E. (2010) High molecular weight persimmon (Diospyros kaki L.) proanthocyanidin: a highly galloylated, A-linked tannin with an unusual flavonol terminal unit, myricetin. J. Agr. Food Chem. 58:9033–9042.10.1021/jf102552bSearch in Google Scholar PubMed
Li, C., Wang, W., Mu, Y.B., Zhang, J.Z., Zhang, S.F., Li, J.Z., Zhang, W. (2018) Structural properties and copolycondensation mechanism of valonea tannin-modified phenol-formaldehyde resin. J. Polym. Environ. 26:1297–1309.10.1007/s10924-017-1008-3Search in Google Scholar
Matthews, S., Mila, I., Scalbert, A., Pollet, B., Lapierre, C., Penhoat, C.L.M.H.D., Rolando, C., Donnelly, D.M.X. (1997) Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles. J. Agr. Food Chem. 45:1195–1201.10.1021/jf9607573Search in Google Scholar
Meagher, L.P., Lane, G., Sivakumaran, S., Tavendale, M.H., Fraser, K. (2004) Characterization of condensed tannins from Lotus species by thiolytic degradation and electrospray mass spectrometry. Anim. Feed Sci. Technol. 117:151–163.10.1016/j.anifeedsci.2004.08.007Search in Google Scholar
Meikleham, N., Pizzi, A., Stephanou, A. (2010) Induced accelerated autocondensation of polyflavonoid tannins for phenolic polycondensates. I. 13C-NMR, 29Si-NMR, X-ray, and polarimetry studies and mechanism. J. Appl. Polym. Sci. 54:1827–1845.10.1002/app.1994.070541206Search in Google Scholar
Nicollin, A., Zhou, X., Pizzi, A., Grigsby, W., Rode, K., Delmotte, L. (2013) MALDI-TOF and 13C NMR analysis of a renewable resource additive-thermoplastic acetylated tannins. Ind. Crop. Prod. 49:851–857.10.1016/j.indcrop.2013.06.013Search in Google Scholar
Oo, C.W., Pizzi, A., Pasch, H., Kassim, M.J. (2008) Study on the structure of mangrove polyflavonoid tannins with MALDI-TOF mass spectrometry. J. Appl. Polym. Sci. 109:963–967.10.1002/app.28135Search in Google Scholar
Osman, Z. (2013) Comparative thermodynamic study on the contribution of the autocondensation and copolymerization reactions for the tannins of the subspecies of Acacia nilotica. J. Polym. Environ. 21:1100–1108.10.1007/s10924-013-0611-1Search in Google Scholar
Pizzi, A. (1980) Tannin-based adhesives. J. Macromol. Sci. Part C 18:247–315.10.1080/00222358008081043Search in Google Scholar
Roumeas, L., Aouf, C., Dubreucq, E., Fulcrand, H. (2013) Depolymerisation of condensed tannins in ethanol as a gateway to biosourced phenolic synthons. Green Chem. 15:3268–3275.10.1039/c3gc41281dSearch in Google Scholar
Santos, J., Delgado, N., Fuentes, J., Fuentealba, C., Vega-Lara, J., Garcia, D.E. (2018) Exterior grade plywood adhesives based on pine bark polyphenols and hexamine. Ind. Crop. Prod. 122:340–348.10.1016/j.indcrop.2018.05.082Search in Google Scholar
Saucier, C., Mirabel, M., Daviaud, F., Longieras, A., Glories, Y. (2001) Rapid fractionation of grape seed proanthocyanidins. J. Agr. Food Chem. 49:5732–5735.10.1021/jf010784fSearch in Google Scholar
Schofield, P., Mbugua, D.M., Pell, A.N. (2001) Analysis of condensed tannins: a review. Anim. Feed Sci. Technol. 91:21–40.10.1016/S0377-8401(01)00228-0Search in Google Scholar
Shi, B., Di, Y. (2000) Plant Polyphenols. Science Press, Beijing. pp. 30–36.Search in Google Scholar
Silva, J.M.R.D., Rigaud, J., Perez-Ilzarbe, J., Cheynier, V. (1991) Micro method for the identification of proanthocyanidin using thiolysis monitored by high-performance liquid chromatography. J. Chromatogr. A 540:401–405.10.1016/S0021-9673(01)88830-0Search in Google Scholar
Teng, B., Jian, X.Y., Gao, Y.P., Chen, W.Y. (2016) Comparison of polyflavonoids in bayberry tanning effluent and commercial bayberry tannin: prerequisite information for vegetable tanning effluent recycling. J. Clean. Prod. 112:972–979.10.1016/j.jclepro.2015.09.005Search in Google Scholar
Venter, P.B., Senekal, N.D., Amra-Jordaan, M., Bonnet, S.L., Van der Westhuizen, J.H. (2012) Analysis of commercial proanthocyanidins. Part 2: an electrospray mass spectrometry investigation into the chemical composition of sulfited quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood extract. Phytochemistry 78:156–169.10.1016/j.phytochem.2012.01.027Search in Google Scholar PubMed
Wen-Xian, L.I., Dan, Y.U., Ling, L., Jing, S., Lan, Z.W., Huo, J.S. (2011) Study on the determination of total polyphenols content in vegatables and fruits by folin-ciocalteu colorimetry. Acta Pharmacol. Sin. 33:302–307.Search in Google Scholar
Yazaki, Y., Hillis, W.E. (1980) Molecular size distribution of radiata pine bark extracts and its effect on properties. Holzforschung 34:125–130.10.1515/hfsg.1980.34.4.125Search in Google Scholar
Zhang, L.L., Chen, J.H., Wang, Y.M., Wu, D.M., Xu, M. (2010) Phenolic extracts from Acacia mangium bark and their antioxidant activities. Molecules 15:3567–3577.10.3390/molecules15053567Search in Google Scholar PubMed PubMed Central
Zhang, J.Z., Kang, H.J., Gao, Q., Li, J.Z., Pizzi, A., Delmotte, L. (2014) Performances of larch (larix gmelini) tannin modified urea-formaldehyde (TUF) resin and plywood bonded by TUF resin. J. Appl. Polym. Sci. 131:547–557.10.1002/app.41064Search in Google Scholar
Zhang, A.B., Li, J.J., Zhang, S.F., Mu, Y.B., Zhang, W., Li, J.Z. (2017a) Characterization and acid-catalysed depolymerization of condensed tannins derived from larch bark. RSC Adv. 7:35135–35146.10.1039/C7RA03410ESearch in Google Scholar
Zhang, J., Liang, J.K., Du, G.B., Zhou, X.J., Wang, H., Lei, H. (2017b) Development and characterization of a bayberry tannin-based adhesive for particleboard. BioResources 12:6082–6093.10.15376/biores.12.3.6082-6093Search in Google Scholar
Zhou, H.C., Lin, Y.M., Li, Y.Y., Li, M., Wei, S.D., Chai, W.M., Tam, F.Y. (2011a) Antioxidant properties of polymeric proanthocyanidins from fruit stones and pericarps of Litchi chinensis Sonn. Food. Res. Int. 44:613–620.10.1016/j.foodres.2010.12.016Search in Google Scholar
Zhou, H.C., Lin, Y.M., Wei, S.D., Tam, N.F.Y. (2011b) Structural diversity and antioxidant activity of condensed tannins fractionated from mangosteen pericarp. Food Chem. 129:1710–1720.10.1016/j.foodchem.2011.06.036Search in Google Scholar
©2019 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Original Articles
- Monitoring fungus infestation of common beech wood using terahertz radiation
- Study of xylan and cellulose interactions monitored with solid-state NMR and QCM-D
- Predicting the lignin H/G ratio of Pinus sylvestris L. wood samples by PLS-R models based on near-infrared spectroscopy
- Kraft lignin reaction with paraformaldehyde
- Exploring the formaldehyde reactivity of tannins with different molecular weight distributions: bayberry tannins and larch tannins
- Chemical analysis and thermal stability of African mahogany (Khaya ivorensis A. Chev) condensed tannins
- Chemical improvement of surfaces. Part 5: surfactants as structural lead for wood hydrophobization – covalent modification with p-alkylated benzoates
- Fracture mechanisms of softwood under longitudinal tensile load at the cell wall scale
Articles in the same Issue
- Frontmatter
- Original Articles
- Monitoring fungus infestation of common beech wood using terahertz radiation
- Study of xylan and cellulose interactions monitored with solid-state NMR and QCM-D
- Predicting the lignin H/G ratio of Pinus sylvestris L. wood samples by PLS-R models based on near-infrared spectroscopy
- Kraft lignin reaction with paraformaldehyde
- Exploring the formaldehyde reactivity of tannins with different molecular weight distributions: bayberry tannins and larch tannins
- Chemical analysis and thermal stability of African mahogany (Khaya ivorensis A. Chev) condensed tannins
- Chemical improvement of surfaces. Part 5: surfactants as structural lead for wood hydrophobization – covalent modification with p-alkylated benzoates
- Fracture mechanisms of softwood under longitudinal tensile load at the cell wall scale