nach oben

European Journal of Wood and Wood Products

Erschienen in:

29.08.2023 | Original Article

Aldehyde-amine crosslinked starch-based high-performance wood adhesive

verfasst von: Chunxiao Yang, Hang Su, Guanben Du, Xiangyu Ren, Yingchen Wu, Huijun Zhang, Kelu Ni, Xin Ran, Jun Li, Wei Gao, Long Yang

Erschienen in: European Journal of Wood and Wood Products | Ausgabe 6/2023

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

Manufacturing green and sustainable bio-based adhesives is an effective strategy to alleviate both serious energy and environmental issues. Herein, based on the aldehyde–amine covalent reaction between dialdehyde starch (DAS) and polyamine (PA_6N), a hyperbranched crosslinked starch-based adhesive was prepared, which overcomes the disadvantage of poor water resistance of conventional starch-based adhesive. The imine groups (C = N) and aminal groups (N–C–N) produced by the reaction of dialdehyde starch and polyamines stably “weld” the molecular chains of dialdehyde starch and polyamine. In addition, the dense cross-linking network formed by the molecular chains stacking and entanglement also plays a crucial role in enhancing the water resistance of the adhesives. The FTIR, XPS, and ¹³C NMR indicated that the imine and aminal covalent bonds were formed between the starch molecular chain and the polyamine. The dry bonding strength of the modified starch adhesive reached 2.12 MPa, which was increased by 162% compared to the natural starch adhesive. The wet strength of the adhesive after 63 °C of hot/boiling water soaking for 3 h broke from 0 to 1.92/1.34 MPa. The proposed DAS-PA_6N starch-based adhesive has the advantages of low cost, high performance, and green sustainability, suggesting broad application prospects in aldehyde-free bio-based wood adhesives.

Vorheriger Artikel Tung oil improves dimensional stability of flattened bamboo

Nächster Artikel An aesthetic transparent wood resistant to Escherichia coli based on interface optimization

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Wirtschaft"

Online-Abonnement

Mit Springer Professional "Wirtschaft" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 340 Zeitschriften

aus folgenden Fachgebieten:

Bauwesen + Immobilien
Business IT + Informatik
Finance + Banking
Management + Führung
Marketing + Vertrieb
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Nur mit Berechtigung zugänglich

Ačkar Đ, Babić J, Jozinović A, Miličević B, Jokić S, Miličević R, Rajič M, Šubarić D (2015) Starch modification by organic acids and their derivatives: a review. Molecules 20(10):19554–19570. https://doi.org/10.3390/molecules201019554CrossRefPubMedPubMedCentral

Arias A, González-Rodríguez S, Barros MV, Salvador R, de Francisco AC, Piekarski CM, Moreira MT (2021) Recent developments in bio-based adhesives from renewable natural resources. J Clean Prod 314:127892. https://doi.org/10.1016/j.jclepro.2021.127892CrossRef

Chen Y, Zhang H, Zhu Z, Fu S (2020) High-value utilization of hydroxymethylated lignin in polyurethane adhesives. Int J Biol Macromol 152:775–785. https://doi.org/10.1016/j.ijbiomac.2020.02.321CrossRefPubMed

Chen L, Din ZU, Yang D, Hu C, Cai J, Xiong H (2021) Functional nanoparticle reinforced starch-based adhesive emulsion: toward robust stability and high bonding performance. Carbohydr Polym 269:118270. https://doi.org/10.1016/j.carbpol.2021.118270CrossRefPubMed

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. https://doi.org/10.1016/j.ijbiomac.2021.11.152CrossRefPubMed

Chi K, Wang H, Catchmark JM (2020) Sustainable starch-based barrier coatings for packaging applications. Food Hydrocolloids 103:105696. https://doi.org/10.1016/j.foodhyd.2020.105696CrossRef

Clasen SH, Müller CM, Parize AL, Pires AT (2018) Synthesis and characterization of cassava starch with maleic acid derivatives by etherification reaction. Carbohydr Polym 180:348–353. https://doi.org/10.1016/j.carbpol.2017.10.016CrossRefPubMed

Din ZU, Chen L, Xiong H, Wang Z, Ullah I, Lei W, Shi D, Alam M, Ullah H, Khan SA (2020) Starch: an undisputed potential candidate and sustainable resource for the development of wood adhesive. Starch-Stärke 72(3–4):1900276. https://doi.org/10.1002/star.201900276CrossRef

Ferdosian F, Pan Z, Gao G, Zhao B (2017) Bio-based adhesives and evaluation for wood composites application. Polymers 9(2):70. https://doi.org/10.3390/polym9020070CrossRefPubMedPubMedCentral

Gendron J, Stambouli I, Bruel C, Boumghar Y, Montplaisir D (2022) Characterization of different types of lignin and their potential use in green adhesives. Ind Crops Prod 182:114893. https://doi.org/10.1016/j.indcrop.2022.114893CrossRef

Gonçalves C, Pereira J, Paiva NT, Ferra JM, Martins J, Magalhães F, Barros-Timmons A, Carvalho L (2018) Statistical evaluation of the effect of urea-formaldehyde resins synthesis parameters on particleboard properties. Polym Test 68:193–200. https://doi.org/10.1016/j.polymertesting.2018.04.007CrossRef

Keimel FA (2003) Historical development of adhesives and adhesive bonding. Handbook of Adhesive Technology. Ind Crops Prod. https://doi.org/10.1016/j.indcrop.2022.114893CrossRef

Konai N, Pizzi A, Raidandi D, Lagel MC, 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 Crops Prod 77:225–231. https://doi.org/10.1016/j.indcrop.2015.08.053CrossRef

Koo SH, Lee KY, Lee HG (2010) Effect of cross-linking on the physicochemical and physiological properties of corn starch. Food Hydrocolloids 24(6–7):619–625. https://doi.org/10.1016/j.foodhyd.2010.02.009CrossRef

Kotynia R, Adamczewska K, Strąkowska A, Masłowski M, Strzelec K (2017) Effect of accelerated curing conditions on shear strength and glass transition temperature of epoxy adhesives. Procedia Eng 193:423–430. https://doi.org/10.1016/j.proeng.2017.06.233CrossRef

Kuakpetoon D, Wang YJ (2001) Characterization of different starches oxidized by hypochlorite. Starch-Stärke 53(5):211–218CrossRef

Laine C, Willberg-Keyriläinen P, Ropponen J, Liitiä T (2019) Lignin and lignin derivatives as components in biobased hot melt adhesives. J Appl Polym Sci 136(38):47983. https://doi.org/10.1002/app.47983CrossRef

Li T, Zhang B, Jiang S, Zhou X, Du G, Wu Z, Cao M, Yang L (2020) Novel highly branched polymer wood adhesive resin. ACS Sustain Chem Eng 8(13):5209–5216. https://doi.org/10.1021/acssuschemeng.9b07732CrossRef

Li Z, Gu M, Du G, Wang J, Liu T, Ni K, Yang H, Tan X, Ran X, Gao W, 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. https://doi.org/10.1021/acssuschemeng.3c01673CrossRef

Liu X, Wang Y, Yu L, Tong Z, Chen L, Liu H, Li X (2013) Thermal degradation and stability of starch under different processing conditions. Starch-Stärke 65(1–2):48–60. https://doi.org/10.1002/star.201200198CrossRef

Liu P, Kang X, Cui B, Gao W, Wu Z, Yu B (2019) Effects of amylose content and enzymatic debranching on the properties of maize starch-glycerol monolaurate complexes. Carbohydr Polym 222:115000. https://doi.org/10.1016/j.carbpol.2019.115000CrossRefPubMed

Liu S, Du G, Yang H, Su H, Ran X, Li J, Zhang L, Gao W, Yang L (2021) Developing high-performance cellulose-based wood adhesive with a cross-linked network. ACS Sustain Chem Eng 9(49):16849–16861. https://doi.org/10.1021/acssuschemeng.1c07012CrossRef

Liu R, Liang M, Xu J, Wang J, Long L, Ni Y (2022) Dialdehyde starch reinforced polyacrylate-polyethylene glycol resin for impregnated decorative paper with improved toughness and ultra-low formaldehyde emission. Ind Crops Prod 176:114390. https://doi.org/10.1016/j.indcrop.2021.114390CrossRef

Luchese CL, Rodrigues RB, Tessaro IC (2021) Cassava starch-processing residue utilization for packaging development. Int J Biol Macromol 183:2238–2247. https://doi.org/10.1016/j.ijbiomac.2021.06.029CrossRefPubMed

Meimoun J, Wiatz V, Saint-Loup R, Parcq J, Favrelle A, Bonnet F, Zinck P (2018) Modification of starch by graft copolymerization. Starch‐Stärke 70(1–2):1600351. https://doi.org/10.1002/star.201600351CrossRef

Ni K, Du G, Liu C, Wu Y, Yang H, Yin C, Su H, Gao RX, Yang W 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(1):142888. https://doi.org/10.1016/j.cej.2023.142888CrossRef

Oktay S, Kızılcan N, Bengü B (2021) Development of bio-based cornstarch-Mimosa tannin-sugar adhesive for interior particleboard production. Ind Crops Prod 170:113689. https://doi.org/10.1016/j.indcrop.2021.113689CrossRef

Pandiselvam R, Manikantan MR, Divya V, Ashokkumar C, Kaavya R, Kothakota A, Ramesh SV (2019) Ozone: an advanced oxidation technology for starch modification. Ozone: Sci Eng 41(6):491–507. https://doi.org/10.1080/01919512.2019.1577128CrossRef

Pang B, Liu H, Rehfeldt F, Zhang K (2021) High internal phase Pickering emulsions stabilized by dialdehyde amylopectin/chitosan complex nanoparticles. Carbohydr Polym 258:117655. https://doi.org/10.1016/j.carbpol.2021.117655CrossRefPubMed

Park S, Park BD (2022) Sustainable bio-based dialdehyde cellulose for transforming crystalline urea–formaldehyde resins into amorphous ones to improve their performance. J Ind Eng Chem 113(25):142–152. https://doi.org/10.1016/j.jiec.2022.05.012CrossRef

Ping L, Brosse N, Chrusciel L, Navarrete P, Pizzi A (2011) Extraction of condensed tannins from grape pomace for use as wood adhesives. Ind Crops Prod 33(1):253–257. https://doi.org/10.1016/j.indcrop.2010.10.007CrossRef

Ren L, Wang Q, Yan X, Tong J, Zhou J, Su X (2016) Dual modification of starch nanocrystals via crosslinking and esterification for enhancing their hydrophobicity. Food Res Int 87:180–188. https://doi.org/10.1016/j.foodres.2016.07.007CrossRefPubMed

Ren J, Li M, Yuan R, Pang A, Lu Z, Ge L (2020) Adherent self-healing chitosan/dialdehyde starch coating. Colloids Surf a 586:124203. https://doi.org/10.1016/j.colsurfa.2019.124203CrossRef

Rovira J, Roig N, Nadal M, Schuhmacher M, Domingo JL (2016) Human health risks of formaldehyde indoor levels: an issue of concern. J Environ Sci Health part a 51(4):357–363. https://doi.org/10.1080/10934529.2015.1109411CrossRef

Sarder R, Piner E, Rios DC, Chacon L, Artner MA, Barrios N, Argyropoulos D (2022) Copolymers of starch, a sustainable template for biomedical applications: a review. Carbohydr Polym 278:118973. https://doi.org/10.1016/j.carbpol.2021.118973CrossRefPubMed

Sasmal D, Banerjee S, Senapati S, Tripathy T (2020) Effective removal of Th4+, Pb²⁺, Cd²⁺, malachite green, methyl violet and methylene blue from their aqueous solution by amylopectin dialdehyde-Schiff base. J Environ Chem Eng 8(3):103741. https://doi.org/10.1016/j.jece.2020.103741CrossRef

Selvakumar G, Lonchin S (2020) Fabrication and characterization of collagen-oxidized pullulan scaffold for biomedical applications. Int J Biol Macromol 164:1592–1599. https://doi.org/10.1016/j.ijbiomac.2020.07.264CrossRefPubMed

Su H, Du G, Ren X, Liu C, Wu Y, Zhang H, Ni K, Yin C, Yang H, Ran X, Li J, Gao W, Yang L (2023) High-performance bamboo composites based on the chemical bonding of active bamboo interface and chitosan. Int J Biol Macromol 244:125345. https://doi.org/10.1016/j.ijbiomac.2023.125345CrossRefPubMed

Sun Y, Gu J, Tan H, Zhang Y, Huo P (2018) Physicochemical properties of starch adhesives enhanced by esterification modification with dodecenyl succinic anhydride. Int J Biol Macromol 112:1257–1263. https://doi.org/10.1016/j.ijbiomac.2018.01.222CrossRefPubMed

Sun Z, Sun B, Bai Y, Gao Z (2021) Economical improvement on the performances of a soybean flour-based adhesive for wood composites via montmorillonite hybridization. Compos Part B: Eng 217:108920. https://doi.org/10.1016/j.compositesb.2021.108920CrossRef

Tan H, Zhang Y, Weng X (2011) Preparation of the plywood using starch-based adhesives modified with blocked isocyanates. Procedia Eng 15:1171–1175. https://doi.org/10.1016/j.proeng.2011.08.216CrossRef

Tang KH, Zhang AL, Ge TJ, Liu XF, Tang XJ, Li YJ (2021) Research progress on modification of phenolic resin. Carbohydr Polym 26:101879. https://doi.org/10.1016/j.mtcomm.2020.101879CrossRef

Vanier NL, El Halal SLM, Dias ARG, da Rosa Zavareze E (2017) Molecular structure, functionality and applications of oxidized starches: a review. Food Chem 221:1546–1559. https://doi.org/10.1016/j.foodchem.2016.10.138CrossRefPubMed

Veelaert S, De Wit D, Gotlieb KF, Verhé R (1997) Chemical and physical transitions of periodate oxidized potato starch in water. Carbohydr Polym 33(2–3):153–162. https://doi.org/10.1016/S0144-8617(97)00046-5CrossRef

Wang Y, Zhang G (2021) The preparation of modified nano-starch and its application in food industry. Food Res Int 140:110009. https://doi.org/10.1016/j.foodres.2020.110009CrossRefPubMed

Watcharakitti J, Win EE, Nimnuan J, Smith SM (2022) Modified starch-based adhesives: a review. Polymers 14(10):2023. https://doi.org/10.3390/polym14102023CrossRefPubMedPubMedCentral

Xing J, Li T, Yu Y, Chen C, Chang J (2018) Development and characterization of a new bio-adhesive for wood using cassava starch and bio-oil. Int J Adhes Adhes 87:91–97. https://doi.org/10.1016/j.ijadhadh.2018.09.005CrossRef

Yang H, Du G, Li Z, Ran X, Zhou X, Li T, Gao W, Li J, Lei H, Yang L (2021) Superstrong adhesive of isocyanate-free polyurea with a branched structure. ACS Appl Polym Mater 3(3):1638–1651. https://doi.org/10.1021/acsapm.1c00056CrossRef

Yang H, Tan X, Du G, Ni K, Wu Y, Li Z, Ran X, Gao W, Li J, 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(15):110872. https://doi.org/10.1016/j.compositesb.2023.110872CrossRef

Yin H, Zheng P, Zhang E, Rao J, Lin Q, Fan M, Zhu Z, Zeng Q, Chen N (2020) Improved wet shear strength in eco-friendly starch-cellulosic adhesives for woody composites. Carbohydr Polym 250:116884. https://doi.org/10.1016/j.carbpol.2020.116884CrossRefPubMed

Yuan J, Du G, Yang H, Liu S, Park S, Liu T, Ran X, Park B, Gao W, Yang L (2023) Fully bio-based Adhesive designed through lignin-cellulose combination and interfacial bonding reinforcement. Industrial Crops & Products 204:117279. https://doi.org/10.1016/j.indcrop.2023.117279CrossRef

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 354:1032–1041. https://doi.org/10.1016/j.cej.2018.08.072CrossRef

Zhang B, Chang Z, Li J, Li X, Kan Y, Gao Z (2019) Effect of kaolin content on the performances of kaolin-hybridized soybean meal-based adhesives for wood composites. Compos Part B: Eng 173:106919. https://doi.org/10.1016/j.compositesb.2019.106919CrossRef

Zhang H, Su Z, Wang X (2022) Starch-based rehealable and degradable bioplastic enabled by dynamic imine chemistry. ACS Sustain Chem Eng 10(26):8650–8657. https://doi.org/10.1021/acssuschemeng.2c02537CrossRef

Zhao XF, Peng LQ, Wang HL, Wang YB, Zhang H (2018) Environment-friendly urea-oxidized starch adhesive with zero formaldehyde-emission. Carbohydr Polym 181:1112–1118. https://doi.org/10.1016/j.carbpol.2017.11.035CrossRefPubMed

Zheng X, Cheng L, Gu Z, Hong Y, Li Z, Li C (2017) Effects of heat pretreatment of starch on graft copolymerization reaction and performance of resulting starch-based wood adhesive. Int J Biol Macromol 96:11–18. https://doi.org/10.1016/j.ijbiomac.2016.12.028CrossRefPubMed

Zuo Y, Liu W, Xiao J, Zhao X, Zhu Y, Wu Y (2017) Preparation and characterization of dialdehyde starch by one-step acid hydrolysis and oxidation. Int J Biol Macromol 103:1257–1264. https://doi.org/10.1016/j.ijbiomac.2017.05.188CrossRefPubMed

Titel: Aldehyde-amine crosslinked starch-based high-performance wood adhesive
verfasst von: Chunxiao Yang
Hang Su
Guanben Du
Xiangyu Ren
Yingchen Wu
Huijun Zhang
Kelu Ni
Xin Ran
Jun Li
Wei Gao
Long Yang
Publikationsdatum: 29.08.2023
Verlag: Springer Berlin Heidelberg
Erschienen in: European Journal of Wood and Wood Products / Ausgabe 6/2023
Print ISSN: 0018-3768
Elektronische ISSN: 1436-736X
DOI: https://doi.org/10.1007/s00107-023-01985-w

Springer Professional

Abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Wirtschaft"

Springer Professional "Technik"

Weitere Artikel der Ausgabe 6/2023

Measurement of surface-checking in sliced lamellae-based engineered wood flooring using digital image correlation

Combined function of glycerol monolaurate/phytol and carnauba wax for improving the hydrophobic and anti-mildew properties of bamboo

Termites infestation on different Eucalyptus wood species and control using natural oil from plants

Study on biological dyeing technology for directional pattern regulation of poplar infected by Lasiodiplodia theobromae

Application status and development prospects of bio-based flame retardants in packaging materials

An aesthetic transparent wood resistant to Escherichia coli based on interface optimization