Skip to main content

Advertisement

SpringerLink
Log in

Wood bonding properties of cellulose cross-linked with a synthesized branched epoxy and enhanced by interfacial covalent bond

  • Original Research
  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

In this study, the aminated cellulose (AC) and branched epoxy (BE) were prepared. After the chlorination and amination of microcrystalline cellulose, its hydroxyl groups were replaced by amino groups. Through thiol-ene click chemical reaction, a branched epoxy was synthesized from trithiocyanuric acid and glycidyl methacrylate. A covalent bond network was formed by epoxy groups crosslinked with amino groups on AC. Furthermore, a new concept of chemical wood bonding interface was adopted on this basis. Due to the hydrolytic condensation of 3-aminopropyltriethoxysilane, the amino groups were grafted onto the surface of wood skeleton for increasing the reactive site and enhancing the synergistic effect between adhesive and interface. By constructing the chemical crosslinking network of “amino-epoxy-amino”, the bonding between adhesive and wood interface got obvious improvement. Compared with the plywood made by natural wood, the dry strength of the plywood prepared by activated wood was increased from 1.46 MPa to 2.19 MPa, which increased by 50%, and the strength of soaking in 63 oC water for 3 h was increased from 0.36 MPa to 2.20 MPa, and the wet strength of boiling water increased from 0 to 0.83 MPa. FT–IR and XPS were used to prove the chemical covalent cross-linking reaction between adhesive and activated wood surface.

Graphical abstract

The preparation of AC-BE adhesive and bonding with activated wood surafce

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Data availability

The materials and data are available from the corresponding author upon reasonable request.

References

  • Averina E, Konnerth J, D’Amico S, van Herwijnen HW (2021) Protein adhesives: alkaline hydrolysis of different crop proteins as modification for improved wood bonding performance. Ind Crops Prod 161:113187

    Article  CAS  Google Scholar 

  • Bai H, Yu C, Zhu H, Zhang S, Ma P, Dong W (2021) Mussel-inspired cellulose-based adhesive with underwater adhesion ability. Cellulose, pp 1–14

  • Chen X, Sun C, Wang Q, Tan H, Zhang Y (2022) Preparation of glycidyl methacrylate grafted starch adhesive to apply in high-performance and environment-friendly plywood. Int J Biol Macromol 194:954–961

    Article  CAS  PubMed  Google Scholar 

  • Chen S, Xu Z, Zhang D (2018) Synthesis and application of epoxy-ended hyperbranched polymers. Chem Eng J 343:283–302

    Article  CAS  Google Scholar 

  • Cho HW, Shi G, Kirkpatrick TR, Thirumalai D (2021) Random first order transition theory for glassy dynamics in a single condensed polymer. Phys Rev Lett 126(13):137801

    Article  CAS  PubMed  Google Scholar 

  • Cudjoe E, Herbert KM, Rowan SJ (2018) Strong, rebondable, dynamic cross-linked cellulose nanocrystal polymer nanocomposite adhesives. ACS Appl Mater Interfaces 10(36):30723–30731

    Article  CAS  PubMed  Google Scholar 

  • Cui C, Fan C, Wu Y, Xiao M, Wu T, Zhang D, Liu W (2019) Water-triggered hyperbranched polymer universal adhesives: from strong underwater adhesion to rapid sealing hemostasis. Adv Mater 31(49):1905761

    Article  CAS  Google Scholar 

  • Cui Y, Lee S, Noruziaan B, Cheung M, Tao J (2008) Fabrication and interfacial modification of wood/recycled plastic composite materials. Compos Part A: Appl Sci Manufac 39(4):655–661

    Article  Google Scholar 

  • Deng S, Du G, Li X, Pizzi A (2014) Performance and reaction mechanism of zero formaldehyde-emission urea-glyoxal (UG) resin. J Taiwan Inst Chem Eng 45(4):2029–2038

    Article  CAS  Google Scholar 

  • Feng Q, Liu H, Peng Z, Zheng Y (2020) Synthesis, characterization and evaluation of long-acting hyperbranched cationic polymer clay stabilizer used in water flooding. Polym Test 82:106344

    Article  CAS  Google Scholar 

  • Hoang HT, Vu TT, Karthika V, Jo SH, Jo YJ, Seo JW, Lim KT (2022) Dual cross-linked chitosan/alginate hydrogels prepared by Nb-Tz ‘click’reaction for pH responsive drug delivery. Carbohydr Polym 288:119389

    Article  CAS  PubMed  Google Scholar 

  • Huang C, Peng Z, Li J, Li X, Jiang X, Dong Y (2022) Unlocking the role of lignin for preparing the lignin-based wood adhesive: a review. Ind Crops Prod 187:115388

    Article  CAS  Google Scholar 

  • Jalali M, Moghadam SR, Baziar M, Hesam G, Moradpour Z, Zakeri HR (2021) Occupational exposure to formaldehyde, lifetime cancer probability, and hazard quotient in pathology lab employees in Iran: a quantitative risk assessment. Environ Sci Pollut Res 28:1878–1888

    Article  CAS  Google Scholar 

  • Jin S, Li K, Zhang X, Gao Q, Zeng L, Shi SQ, Li J (2020) Phytic acid-assisted fabrication for soybean meal/nanofiber composite adhesive via bioinspired chelation reinforcement strategy. J Hazard Mater 399:123064

    Article  CAS  PubMed  Google Scholar 

  • Jing J, Liang S, Yan Y, Tian X, Li X (2019) Fabrication of hybrid hydrogels from silk fibroin and tannic acid with enhanced gelation and antibacterial activities. ACS Biomater Sci Eng 5(9):4601–4611

    Article  CAS  PubMed  Google Scholar 

  • Kaboorani A, Riedl B, Blanchet P, Fellin M, Hosseinaei O, Wang S (2012) Nanocrystalline cellulose (NCC): a renewable nano-material for polyvinyl acetate (PVA) adhesive. Eur Polymer J 48(11):1829–1837

    Article  CAS  Google Scholar 

  • Li Z, Gu M, Du G, Wang J, Liu T, Ni K, Yang L (2023) Integration of aromatic polyurea and dialdehyde cellulose as high-performance hybrid resin adhesives for bonding wood. ACS Sustain Chem Eng 11(32):11878–11889

    Article  CAS  Google Scholar 

  • Li YD, Jian XY, Zhu J, Du AK, Zeng JB (2018) Fully biobased and high performance epoxy thermosets from epoxidized soybean oil and diamino terminated polyamide 1010 oligomers. Polym Test 72:140–146

    Article  CAS  Google Scholar 

  • Li K, Jin S, Wei Y, Li X, Li J, Shi SQ, Li J (2021) Bioinspired hyperbranched protein adhesive based on boronic acid-functionalized cellulose nanofibril and water-soluble polyester. Compos Part B: Eng 219:108943

    Article  CAS  Google Scholar 

  • Li K, Jin S, Zhou Y, Zhang F, Zeng G, Li J, Li J (2022a) Bioinspired dual-crosslinking strategy for fabricating soy protein-based adhesives with excellent mechanical strength and antibacterial activity. Compos Part B: Eng 240:109987

    Article  CAS  Google Scholar 

  • Li Z, Sun Y, Pang H, Ma C, Mo L, Zhang S (2022b) Synthesis of cationic waterborne polyurethane via thiol-ene click reaction and catechol chemistry to improve the performance of soybean meal adhesives. Ind Crops Prod 183:114982

    Article  CAS  Google Scholar 

  • Li Q, Zhu L, Liu R, Huang D, Jin X, Che N, Huang Y (2012) Biological stimuli responsive drug carriers based on keratin for triggerable drug delivery. J Mater Chem 22(37):19964–19973

    Article  CAS  Google Scholar 

  • Lin F, Wang Z, Chen J, Lu B, Tang L, Chen X, Chen Y (2020) A bioinspired hydrogen bond crosslink strategy toward toughening ultrastrong and multifunctional nanocomposite hydrogels. J Mater Chem B 8(18):4002–4015

    Article  CAS  PubMed  Google Scholar 

  • Liu T, Du G, Wu Y, Liu C, Yang H, Ni K, Yang L (2023) Activated wood surface and functionalized cellulose co-building strong chemical wood bonding performance. Carbohydr Polym 305:120573

    Article  CAS  PubMed  Google Scholar 

  • Liu S, Du G, Yang H, Su H, Ran X, Li J, Yang L (2021) Developing high-performance cellulose-based wood adhesive with a cross-linked network. ACS Sustain Chem Eng 9(49):16849–16861

    Article  CAS  Google Scholar 

  • Liu S, Wu Y, Du G, Yang H, Ni K, Su H, Yang L (2022) H2O2-mediated tannin bio-based wood adhesive inspired by starfish structure and phenol-amine synergy. Ind Crops Prod 188:115714

    Article  CAS  Google Scholar 

  • Ma Y, Wang Y, Zhang Y, Wang H, Gu J, Li N, Zhang Y (2023) Preparation of isocyanate virtual ‘core-shell’ and its application in wood adhesive. Int J Adhes Adhes 124:103379

    Article  CAS  Google Scholar 

  • Maulana MI, Lubis MA, R, Febrianto F, Hua LS, Iswanto AH, Antov P, Todaro L (2022) Environmentally friendly starch-based adhesives for bonding high-performance wood composites: a review. Forests 13(10):1614

    Article  Google Scholar 

  • Ni K, Du G, Liu C, Wu Y, Yang H, Yin C, Yang L (2023) Cross-linked entanglement of aldehyde and amine-functionalized nanocellulose reinforced with biomineralization to produce an all-bio-based adhesive. Chem Eng J 465:142888

    Article  CAS  Google Scholar 

  • Pei W, Shang W, Liang C, Jiang X, Huang C, Yong Q (2020) Using lignin as the precursor to synthesize Fe3O4@ lignin composite for preparing electromagnetic wave absorbing lignin-phenol-formaldehyde adhesive. Ind Crops Prod 154:112638

    Article  CAS  Google Scholar 

  • Qi Z, Wang B, Sun C, Yang M, Chen X, Zheng D, Zhang Y (2022) Comparison of properties of poly (lactic acid) composites prepared from different components of corn straw fiber. Int J Mol Sci 23(12):6746

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Rong LH, Cheng X, Ge J, Krebs OK, Capadona JR, Caldona EB, Advincula RC (2023) Synthesis of hyperbranched polymer films via electrodeposition and oxygen-tolerant surface-initiated photoinduced polymerization. J Colloid Interface Sci 637:33–40

    Article  CAS  PubMed  Google Scholar 

  • Rowell RM (2021) Understanding wood surface chemistry and approaches to modification: a review. Polymers 13(15):2558

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Su H, Du G, Ren X, Liu C, Wu Y, Zhang H, Yang L (2023) High-performance bamboo composites based on the chemical bonding of active bamboo interface and chitosan. Int J Biol Macromol 244:125345

    Article  CAS  PubMed  Google Scholar 

  • Su H, Du G, Yang H, Wu Y, Liu S, Ni K, Yang L (2022a) Novel ultrastrong wood bonding interface through chemical covalent crosslinking of aldehyde-amine. Ind Crops Prod 189:115800

    Article  CAS  Google Scholar 

  • Su M, Wu J, Pan P, Wang H (2022a) Preparation and characterization of a water-resistant polyamide-oxidized starch-methyl methacrylate eco-friendly wood adhesive. Int J Biol Macromol 194:763–769

    Article  CAS  PubMed  Google Scholar 

  • Tan B, Ji Y, Hu Y, Yuan B, Hu X, Huang Z (2020) Pretreatment using diluted epoxy adhesive resin solution for improving bond strength between steel and wood surfaces. Int J Adhes Adhes 98:102502

    Article  CAS  Google Scholar 

  • Umar A, Naim AA, Sanagi MM (2014) Synthesis and characterization of chitosan grafted with polystyrene using ammonium persulfate initiator. Mater Lett 124:12–14

    Article  CAS  Google Scholar 

  • Umar A, Sanagi MM, Salisu A, Ibrahim WA, W, Abd Karim KJ, Keyon ASA (2016) Preparation and characterization of starch grafted with methacrylamide using ammonium persulphate initiator. Mater Lett 185:173–176

    Article  CAS  Google Scholar 

  • Venault A, Liou CS, Yeh LC, Jhong JF, Huang J, Chang Y (2017) Turning expanded poly (tetrafluoroethylene) membranes into potential skin wound dressings by grafting a bioinert epoxylated PEGMA copolymer. ACS Biomater Sci Eng 3(12):3338–3350

    Article  CAS  PubMed  Google Scholar 

  • Wang Y, Chen S, Guo W, Miao M, Zhang D (2019) The precise effect of degree of branching of epoxy-ended hyperbranched polymers on intrinsic property and performance. Prog Org Coat 127:157–167

    Article  CAS  Google Scholar 

  • Wei C, Zhu X, Peng H, Chen J, Zhang F, Zhao Q (2019) Facile preparation of lignin-based underwater adhesives with improved performances. ACS Sustain Chem Eng 7(4):4508–4514

    Article  CAS  Google Scholar 

  • Wu Z, Deng X, Li L, Xi X, Tian M, Yu L, Zhang B (2021) Effects of heat treatment on interfacial properties of Pinus massoniana wood. Coatings 11(5):543

    Article  CAS  Google Scholar 

  • Xu P, Du X, Cong P, Zhou Z (2022) Properties of paving epoxy asphalt with epoxy-terminated hyperbranched polyester. Road Mater Pavement Des 23(1):234–246

    Article  CAS  Google Scholar 

  • Yan Q, Ma C, Liang Z, Zhang S (2022) High-temperature soybean meal adhesive based on disulfide bond rearrangement and multiple crosslinking: water resistance and prepressing adhesion. J Clean Prod 373:133709

    Article  CAS  Google Scholar 

  • Yang H, Du G, Ni K, Wu Y, Ran X, Tan X, Yang L (2023) Development of high-performance sucrose-based adhesives with high density cross-linking network inspired by Maillard reaction or cuisine chemistry. Ind Crops Prod 195:116416

    Article  CAS  Google Scholar 

  • Yang C, Jiang Y, Chen F, Zhao J (2023) Highly Elastic hyperbranched polymer binder for silicon anodes in lithium-ion batteries. Electrochim Acta 442:141805

    Article  CAS  Google Scholar 

  • Yang H, Tan X, Du G, Ni K, Wu Y, Li Z, Yang L (2023) Development of biomass adhesives based on aminated cellulose and oxidized sucrose reinforced with epoxy functionalized wood interface. Compos Part B: Eng 263:110872

    Article  CAS  Google Scholar 

  • Yang X, Tu Q, Shen X, Pan M, Jiang C, Lai X, Xue J (2020) Synergistic modification by mercapto hyperbranched polysiloxane and functionalized graphene oxide on the surface of aramid fiber. Polym Test 91:106783

    Article  CAS  Google Scholar 

  • Yuan J, Du G, Yang H, Liu S, Wu Y, Ni K, Li J (2022) Functionalization of cellulose with amine group and cross-linked with branched epoxy to construct high-performance wood adhesive. Int J Biol Macromol 222:2719–2728

    Article  CAS  PubMed  Google Scholar 

  • Zhao S, Pang H, Li Z, Wang Z, Kang H, Zhang W, Li L (2021) Polyurethane as high-functionality crosslinker for constructing thermally driven dual-crosslinking plant protein adhesion system with integrated strength and ductility. Chem Eng J 422:130152

    Article  CAS  Google Scholar 

  • Zhao D, Qiu G, Li X, Wan C, Lu K, Chung TS (2016) Zwitterions coated hollow fiber membranes with enhanced antifouling properties for osmotic power generation from municipal wastewater. Water Res 104:389–396

    Article  CAS  PubMed  Google Scholar 

  • Zhao S, Wang Z, Li Z, Li L, Li J, Zhang S (2019) Core–shell nanohybrid elastomer based on co-deposition strategy to improve performance of soy protein adhesive. ACS Appl Mater Interfaces 11(35):32414–32422

    Article  CAS  PubMed  Google Scholar 

  • Zidanes UL, Dias MC, Lorenço MS, da Silva Araujo E, Ferreira e Silva MJ, Sousa TB, Mori FA (2021) Preparation and characterization of tannin-based adhesives reinforced with cellulose nanofibrils for wood bonding. Holzforschung 75(2):159–167

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Not applicable.

Funding

This work was financially supported by the Applied Basic Research Foundation of Yunnan Province (Nos. 202301AS070041, 202101AT070047) and the National Natural Science Foundation of China (Nos. 32171884, 32060323, 32071688). L.Y. acknowledges candidates of the Young and Middle-Aged Academic Leaders of Yunnan Province (202105AC160048) and the Ten Thousand Talent Program for Young Top-notch Talents of Yunnan Province (YNWR-QNBJ-2020-136). X.R. acknowledges the Xingdian Talent Support Program Young Talents in Yunnan Province (XDYC-QNRC-2022-0228). G.D. acknowledges the Program for Leading Talents (No. 2017HA013), the 111 Project (D21027), and the Yunnan Provincial Academician Workstation (YSZJGZZ-2020052).

Author information

Authors and Affiliations

  1. Yunnan Province Key Lab of Wood Adhesives and Glued Products, International Joint Research Center for Biomass Materials, Southwest Forestry University, Kunming, 650224, China

    Siyao Xie, Tongda Liu, Haozhang Wen, Guanben Du, Hongxing Yang, Sichen Liu, Kelu Ni, Hang Su, Xin Ran, Wei Gao & Long Yang

  2. Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains, Ministry of Education, Southwest Forestry University, Kunming, 650224, China

    Guanben Du & Long Yang

Authors
  1. Siyao Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tongda Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Haozhang Wen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Guanben Du
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hongxing Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sichen Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Kelu Ni
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Hang Su
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Xin Ran
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Wei Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Long Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

SX: Experiment, Investigation, Formal analysis, Writing – original draft. TL: Investigation, Formal analysis, Writing – original draft. HW: Formal analysis, Writing – original draft. GD: Writing – review & editing. Funding acquisition. HY: Investigation, Formal analysis SL: Experiment, Formal analysis. KN: Draw, Investigation. HS: Investigation, Formal analysis. XR: Funding acquisition. WG: Resources. LY: Conceptualization, Writing – review & editing, Supervision, Funding acquisition.

Corresponding authors

Correspondence to Guanben Du or Long Yang.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Ethical approval

Not applicable.

Consent for publication

All the authors read the manuscript and agree with the publication of this manuscript.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xie, S., Liu, T., Wen, H. et al. Wood bonding properties of cellulose cross-linked with a synthesized branched epoxy and enhanced by interfacial covalent bond. Cellulose 31, 1175–1187 (2024). https://doi.org/10.1007/s10570-023-05679-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-023-05679-7

Keywords

Search

Navigation