Boiling Water Resistant Fully Bio-Based Adhesive Made from Maleated Chitosan and Glucose with Excellent Performance

doi:10.21203/rs.3.rs-2948331/v1

Download PDF

Research Article

Boiling Water Resistant Fully Bio-Based Adhesive Made from Maleated Chitosan and Glucose with Excellent Performance

https://doi.org/10.21203/rs.3.rs-2948331/v1

This work is licensed under a CC BY 4.0 License

Version 1

posted

You are reading this latest preprint version

Preparing green wood adhesives using renewable biomass resources is significant. A three-component biomass adhesive CSC-G was prepared by combining chitosan, maleic anhydride, and glucose. Characterization using Fourier transform infrared (FTIR), X-ray photoelectron spectroscopy (XPS), and X-ray diffraction (XRD) demonstrated that dehydrated malic acid serves as a bridge for connecting chitosan and glucose. The introduction of glucose enriches the crosslinking density, thereby improving the bonding strength. In addition, the effects of the mass ratio of CSC to glucose, hot pressing temperature, and hot-pressing time on CSC-G adhesive were also investigated. The excellent performance of CSC-G is mainly shown in that when pressed at 160 ℃, the shear strength of three-layer plywood remains at 0.88 MPa after soaking in boiling water for 3 hours, and the curing temperature is better than the previously reported polyester adhesive. As an all-biomass polyester adhesive, CSC-G adhesive has a lower curing temperature and excellent performance and provides a new approach to developing high-performance chitosan-based wood adhesives.

Biomass

Wood adhesive

Chitosan

Graft modification

Water resistance

The development of the wood industry cannot be separated from the wide application of adhesives [1, 2]. Urea formaldehyde, phenolic aldehyde, and melamine are currently the most widely used wood adhesives [3, 4], and will still occupy a dominant position in wood adhesives in the future [5, 6]. The use of these adhesives may be accompanied by potential formaldehyde pollution issues and oil resource consumption issues [7, 8]. Therefore, developing non-toxic and renewable green adhesives is very important from a long-term perspective.

Preparing high-performance wood adhesives using biomass materials has been a hot research topic [9–11]. The preparation of bio-based adhesives to alleviate the potential pollution of formaldehyde-based adhesives and reduce dependence on non-renewable petroleum resources is significant and challenging [12]. Many scholars have overcome the problems of poor adhesive strength and water resistance of biomass adhesives by modifying and modifying lignin, tannin, cellulose, protein, etc., and have shown promising potential in the preparation of wood adhesives [13–16]. Like other biomass materials, chitosan has the potential to be used as an adhesive in the wood industry [17].

Chitosan (CS) is a product of partial acetylation removal from chitin [18]. It is a widely sourced and renewable biomacromolecule polymer that can be extracted from fishery wastes such as shrimp shells or crab shells [19, 20]. Based on the fact that chitosan is the only basic polysaccharide among natural polysaccharides, it has excellent biological properties and can be chemically modified [21]. Chitosan has been chemically modified to improve its utilization, making it widely used in medicine, nanomaterials, food packaging, and other fields [22–25]. Like other biomass materials, chitosan has the potential to be used as an adhesive in the wood industry. However, there are relatively few studies on the application of chitosan in wood adhesives.

The poor solubility of chitosan and the short amino molecular chain limit its application [26]. Many scholars have converted chitosan into corresponding derivatives through grafting, cross-linking, and degradation methods [27, 28]. These modifications include acylation, esterification, etherification, and degradation, which improve the solubility and mechanical strength of chitosan while maintaining its unique properties [29, 30]. Inspired by the above modification and modification methods, we promote the functionalization of chitosan and its derivatives through the grafting of functional groups to improve the inherent defects of chitosan.

In this work, firstly, maleic anhydride was used to carboxylate chitosan to prepare carboxy chitosan (CSC). Characterization have demonstrated that maleic anhydride acts as a “bridge” for connecting chitosan and glucose. Compared with CS and CSC, the water solubility of CSC-G has been dramatically improved and can be used as a wood adhesive (Fig. 1). CSC has a longer molecular chain and can effectively cross-link with glucose, resulting in better adhesive strength and water resistance. As an all-biomass adhesive, CSC-G adhesive not only meets the requirements of sustainable development, but also provides a reference for modifying chitosan and preparing chitosan-based biological adhesive.

2.1 Materials

Chitosan (CS; deacetylation degree ≥ 85%), glucose, and maleic anhydride (MA) were purchased from Shanghai Adamas Reagent Co., Ltd. (Shanghai, China). Poplar veneers were purchased from a local lumber mill. The solvent used in the experiment was deionized water.

2.2 Preparation of CSC

15 g of maleic anhydride was heated to melting at 90 ℃, then 2.5 g of chitosan was slowly added. After 6 h of reaction, hot deionized water was added to quench the reaction. The mixture is filtered, washed, and dried at room temperature to obtain carboxylated chitosan (CSC).

2.3 Preparation of CSC-G adhesives

The synthesis of CSC-G adhesive is shown in Scheme 1. Add the dried CSC and glucose into the flask according to different mass ratios (the mass of CSC and glucose is 1:2, 1:1, 2:1, respectively), and add deionized water to make the solid content 40% (Table 1). Reaction at 90 ℃ for 5 h to obtain yellow-brown CSC-G adhesive.

2.4 Fourier-transform infrared spectroscopy (FTIR) analysis

The samples were scanned by attenuated total reflection infrared spectrometer (Thermo Scientific Nicolet iS50) with wavenumbers ranging from 400 to 4000 cm^− 1 for 32 scans with a resolution of 4 cm^− 1.

2.5 X-ray photoelectron spectroscopy (XPS) analysis

XPS was conducted on a Thermo ScientificTM K-AlphaTM⁺ spectrometer equipped with a monochromatic Al Kα X-ray source (1486.6 eV) operating at 100 W. All peaks would be calibrated with C1s peak binding energy at 284.8 eV for adventitious carbon.

2.6 Thermal performance analysis

The thermal properties of CS, CSC, and CSC-G adhesive were determined by differential scanning calorimetry (DSC; NETZSCH DSC204F1) and thermogravimetric analysis (TGA; NETZSCH TG209F1) in a nitrogen protected atmosphere.

2.7 X-ray diffraction (XRD) analysis

XRD (ARL EQUINOX 300, Thermo Fisher Scientific, France) was used to record the diffraction peaks at 10–55° at a 2°/min rate.

2.8 Gel permeation chromatography (GPC) determinations

The molecular weight determinations of CS and CSC-G adhesive were carried out on a Waters 1525 gel permeation chromatography (GPC) (Table 2).

2.9 Test and analysis of adhesive properties

The prepared CSC-G adhesives were used to prepare three-layer plywood to evaluate adhesive properties. Three-layer plywood panels were prepared by spreading the adhesive on double sides of the central layer at 200 g/m². Hot-pressing parameters were 200 ℃, 1.0 MPa, and 5 min. After the plywood is allowed to stand for 12 hours at room temperature, the three-layer plywood is sawn into test pieces (100 × 25 mm), and the adhesive area remains 25 × 25 mm. The shear strength of plywood specimens was evaluated according to GB/T 17657 − 2013 standard.

3.1 Characterization results of CSC-G adhesive

Table 1

Compositions of the CSC-G adhesives.
Adhesives	CSC (g)	Glucose (g)	Distilled water (g)
CSC-G	6	6	18
CSC-2G	4	8	18
2CSC-G	8	4	18

Table 2

GPC results of Chitosan and CSC-G adhesive.
Samples	Mn	Mw	PDI
Chitosan	8140	30008	3.65
CSC-G adhesive	15033	37300	2.48

FTIR analysis

Figure 2 shows the FTIR spectra of CS, CSC, and CSC-G adhesive. The broad absorption band of CS at 3450 cm^− 1 attributed to N-H and O-H tensile vibrations [31, 32], with 1090 cm^− 1 being the tensile vibration of CH₂-O-CH₂. In addition, the peaks at 1598 and 1320 cm^− 1 belong to the typical N-H bending and C-N tensile vibrations of chitosan [17], respectively. The peak of 1660 cm^− 1 is attributed to the C = O stretching vibration of the residual amide bond in chitin. Compared with CS, the infrared spectrum of CSC shows significant changes. Firstly, due to the consumption of -NH₂ and -OH, the peak located at 3450 cm^− 1 was significantly weakened. A peak attributed to C = O was generated at 1706 cm^− 1, proving that MA reacted with chitosan and produced amide or ester groups. Secondly, compared to CSC, the absorption peak in CSC-G shifted from 1706 cm^− 1 to 1714 cm^− 1, and the peak width was significantly enhanced, indicating that the carboxyl groups in CSC reacted with the hydroxyl groups on glucose to generate more esters [33], forming a cross-linked structure. In addition, a new broad peak appeared at 3600 cm^− 1, which belongs to the hydroxyl group on glucose [34], indicating that the adhesive contains many hydrogen bonds, which is also why CSC-G has good bonding performance. The above results indicate that maleic anhydride acts as a “bridge” to connect chitosan and glucose, forming a densely cross-linked network structure.

¹³ C NMR analysis

In addition, the chemical structures of CS, CSC and CSC-G were further analyzed by ¹³C NMR. As can be seen from Fig. 3, both CSC and CSC-G, as derivatives of chitosan, have obvious unit absorption peaks of D-anhydroglucopyranose units (AGUs) [32]. Chemical shift peaks less than 100 ppm are attributed to C1-6 or C11-16, and have different chemical shift values in different environments, which is consistent with previous reports [32]. In the spectra of CSC, three new absorption peaks were detected at 169.8, 162.5, and 131.8 ppm, which were attributed to C7, C10, C8, and C9, respectively. These three new signals prove that CS and MA react successfully to obtain CSC. Compared with CSC, the peak of CSC-G at 162.5 ppm disappeared and moved to 169.2 ppm, indicating that the carboxyl and glucose reactions on CSC were consumed to form ester groups [34]. The above results provided strong evidence for the successful preparation of CSC-G adhesive.

XPS analysis

To better understand the changes in the adhesive before and after curing, XPS analysis was conducted on CS, CSC-G adhesive, and cured CSC-G adhesive (Fig. 4). Upon comparing Fig. 4a and c, it is evident from the high-resolution spectra of C1s in both figures that a new peak at 288.7 eV has emerged, which can be attributed to C = O [35, 36]. The results indicate that maleic anhydride acts as a bridge to connect CS and glucose. The content of O atom in uncured CSC-G adhesive is 14.96%, and the content of O bonds in cured CSC-G adhesive is 26.47%, indicating a decrease in C-O bonds after resin curing (Fig. 4f). This may be better than the thermal pressing process, where glucose is dissociated from the cross-linked network and undergoes pyrolysis or dehydration to form anhydride [34]. High temperature is beneficial for the generation of esters while also leading to a decrease in -OH content and an increase in C = O bonds in the adhesive. These analysis results are consistent with infrared spectroscopy, indicating the composition of the cross-linking network and the successful preparation of CSC-G adhesive.

Thermal performance analysis

DSC

The curing behavior of CSC-G adhesive was studied through DSC analysis. Compared to CS and CSC, CSC-G adhesive has significant endothermic peaks. The curing temperatures of CSC-G, CSC-2G, and 2CSC-G are 135.9 ℃, 151.5 ℃, and 155.6 ℃, respectively (Fig. 5). The addition of too much CSC or glucose is not conducive to solidification. In addition, no other exothermic peaks were found in the 170–230 ℃ range, indicating that the reaction between CSC and glucose is complete at 5 hours. Among them, the CSC-G adhesive has the lowest curing temperature, which indicates that its curing degree is more complete and its performance is more excellent than other adhesives under the same curing conditions. According to the DSC curve, the optimal curing temperature for CSC-G adhesive is 160 ℃. However, according to previous reports, polyester adhesives require a higher curing temperature [33, 34]. Therefore, we first set the hot-pressing temperature at 200 ℃ to select the optimal CSC-G adhesive ratio and optimize the hot-pressing parameters in subsequent experiments.

To explain the cross-linking network of CSC-G and explore the thermal stability of CS derivatives, TG testing was conducted. For all test samples, the mass loss at 30–120 ℃ is attributed to the evaporation of polymer moisture (Fig. 6). CS (T_max=300 ℃) due to the destruction or degradation of molecular chains [35]. The decomposition temperature of CSC-G tends to increase, because the high density of covalent bonds in the CSC-G network structure is conducive to the thermal stability of CSC-G adhesive [36]. The rapid decomposition of the CSC-G adhesive began at 345.98 ℃, indicating that the CSC-G adhesive has satisfactory thermal stability. At 200 ℃, the mass loss of CSC-G is only 7.77%, indicating that CSC-G is more stable due to the formation of cross-linking networks. It also indicates that short-term hot pressing at 200 ℃ will not cause significant decomposition of cured CSC-G.

XRD analysis

As shown in Fig. 7, CS has a strong diffraction peak at 20.3°, which is caused by the semi-crystalline nature of chitosan itself [37], resulting from the free amino groups on the chitosan molecule and internal hydrogen bonds. Compared with CS, the diffraction curve of CSC is relatively more tortuous, and a new diffraction peak appears near 12.3°, indicating that carboxylation of chitosan through maleic anhydride increases the crystallinity of chitosan [38]. After the addition of glucose, the peak located at 12.3° disappeared. The peak at 20.3° showed slight displacement and significant weakening, indicating that the multiple interactions of esterification reaction and spatial rearrangement formed more coordination bonds and intermolecular hydrogen bonds, resulting in a certain decrease in crystallinity. The emergence of new crystallization peaks at 28.72° may be the reason for the excellent water resistance of CSC-G adhesive [39].

Mechanical properties

CS and CSC have poor solubility in water, so they cannot be used as wood adhesives in this experiment. But CSC-G exhibits good water solubility, which may be related to adding glucose structure, which brings more hydroxyl groups. The ratio of CSC to glucose has a significant impact on the water resistance of plywood. As shown in Fig. 8a, CSC-2G adhesive did not exhibit superior boiling water resistance under 200 ℃ hot-pressing conditions. The addition of excessive glucose results in insufficient CSC to react with it, leading to the presence of a large amount of glucose or byproducts free from the cross-linking network in the adhesive system, resulting in a decrease in the performance of the plywood. The high cross-linking degree helps improve the cured adhesive's shear strength (Table 2). CSC-G adhesive is prepared by reacting carboxyl groups on CSC and hydroxyl groups on glucose, a dynamic equilibrium reaction of ester product synthesis and hydrolysis. Therefore, a higher hot-pressing temperature is conducive to the esterification reaction and the curing of CSC-G adhesive and to increasing the adhesive's cohesion and adhesion to the wood surface. Overall, C = O, - OH, and hydrogen bonding endow the adhesive with excellent properties. Considering that reducing temperature and hot-pressing time can reduce energy consumption in the actual production process, and CSC-G adhesive with a CSC/G mass ratio of 1.0 has better water resistance, we took CSC-G adhesive as the experimental object and optimized the hot-pressing conditions by changing the hot pressing temperature and time. As shown in Fig. 8b, CSC-G adhesive showed good heat resistance (0.88 MPa) even when the temperature was reduced to 160 ℃. The effective way to reduce the pressing temperature and obtain satisfactory bond strength is to prolong the pressing time with a lower temperature [40]. To our delight, after hot pressing at 180 ℃ for 3 min and soaking in hot and boiling water for 3 h, the wet shear strength was 0.83 MPa and 0.71 MPa, respectively, which was higher than the relevant standards (Fig. 8c). Considering that the DSC peak of CSC-G is 135.9 ℃ (Fig. 5), CSC-G adhesive was hot pressed at 140 ℃ for different times, and the results are shown in Fig. 8d. Under the hot pressed condition, CSC-G adhesive still has certain performance. Different types of wood fracture can be observed in Fig. 8e, indicating that with the increase of temperature, the wood loss rate increases, the permeability of the adhesive to the wood increases, and the mechanical interlocking behavior of the wood glue interface is enhanced. Compared with adhesives with similar structures or similar preparation mechanisms, it can be found that the CSC-G adhesive prepared in this study has better curing temperature and mechanical properties (Table 3). In addition, the raw materials of the prepared adhesive are all from biomass and have no formaldehyde release. As a green and environmentally friendly biomass polyester adhesive, it has a good application prospect in the wood industry.

Table 3

Comparison of wet shear strength between CSC-G adhesive and adhesive with similar synthesis mechanism or structure under hot-pressing temperature for three-plywood.
Adhesives	Hot pressing temperature/℃	Hot water shear strength/MPa	Boiling water shear strength/MPa	Reference
CAG	200	1.33	1.35	[34]
HBPCA	200	1.49	1.47	[33]
P-OS-M	180	1.04	-	[41]
CHG	180	1.37	-	[42]
CH	200	1.24	-	[43]
CS	160	0.65	-	[17]
CSC-G	160	0.79	0.82	This work
	180	1.25	1.15
	200	1.5	1.39

In this work, a three-component all-biomass wood adhesive (CSC-G) with high water resistance was prepared based on chitosan. Maleic anhydride acts as a "bridge" to connect chitosan and glucose, and covalent and hydrogen bonds improve the inherent defects of biomass adhesives and increase the bonding strength. Carboxylated chitosan prolongs the chain of chitosan molecules, making it more fully cross-linked to glucose. Due to the increased molecular weight, the thermal stability of the CSC-G adhesive was also enhanced. CSC-G adhesives exhibited lower curing temperature than other polyester adhesives. CSC-G showed good water resistance even when hot pressed at 160 ^oC. This strategy expands the use of fishery waste chitosan and provides a new way to modify chitosan and prepare chitosan-based adhesives with excellent performance.

Declaration of competing interest

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

Author Contribution

Heyang Zeng performed investigation, methodology, data curation, formal analysis, funding acquisition, and writing- original draft. Tao Jin performed data curation and formal analysis. Senlei Shi performed formal analysis, visualization. Li Liu performed methodology and supervision. Haiyang Guo performed supervision and writing-review & editing. Linkun Xie performed supervision and software. Xijuan Chai performed supervision. Kaimeng Xu performed methodology and supervision. Guanben Du performed funding acquisition, supervision and writing-review & editing. Lianpeng Zhang performed project administration, funding acquisition, and writing-review & editing. All authors reviewed the manuscript.

Statement for Funding information

This work is supported by the Yunnan Fundamental Research Project (202201AU070071 and 202301AT070224), Natural Science Foundation of China (22161043 and 21801096), High-level Talent Introduction Program Project of Yunnan Province (YNQR-QNRC-2019-065), Yunnan Provincial Department of Education Project (2022Y554 and 2023Y0702), and the Start up Funding of Southwest Forestry University (112126), also the 111 Project (D21027).

Data availability

No data was used for the research described in the article.

Bandara N, Wu J (2018) Chemically Modified Canola Protein–Nanomaterial Hybrid Adhesive Shows Improved Adhesion and Water Resistance. ACS Sustainable Chem Eng 6(1):1152–1161. https://doi.org/10.1021/acssuschemeng.7b03457
Wang Z, Kang H, Liu H, Zhang S, Xia C, Wang Z, Li J (2020) Dual-Network Nanocross-linking Strategy to Improve Bulk Mechanical and Water-Resistant Adhesion Properties of Biobased Wood Adhesives. ACS Sustainable Chem Eng 8(44):16430–16440. https://doi.org/10.1021/acssuschemeng.0c04913
Gonçalves C, Paiva NT, Ferra JM, Martins J, Magalhães F, Barros-Timmons A, Carvalho L (2018) Utilization and characterization of amino resins for the production of wood-based panels with emphasis on particleboards (PB) and medium density fibreboards (MDF). A review. Holzforschung 72(8):653–671. https://doi.org/10.1515/hf-2017-0182
Pizzi A, Papadopoulos AN, Policardi F (2020) : Wood Composites and Their Polymer Binders, Polymers 12(5), 1115 https://doi.org/10.3390/polym12051115
Jiang S, Wang S, Du G, Hu M, Qian Z, Shi Z, Zhou X, Li T (2022) Highly Branched Polyurea-Based Resins: Clean Synthesis and Wood Bonding Performance. ACS Sustainable Chem Eng 10(21):7205–7214. https://doi.org/10.1021/acssuschemeng.2c01916
Xu Y, Guo L, Zhang H, Zhai H, Ren H (2019) Research status, industrial application demand and prospects of phenolic resin. RSC Adv 9(50):28924–28935. https://doi.org/10.1039/C9RA06487G
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/polym9020070
Gu W, Li F, Liu X, Gao Q, Gong S, Li J, Shi SQ (2020) Borate chemistry inspired by cell walls converts soy protein into high-strength, antibacterial, flame-retardant adhesive. Green Chem 22(4):1319–1328. https://doi.org/10.1039/C9GC03875B
Li RJ, Gutierrez J, Chung Y-L, Frank CW, Billington SL, Sattely ES (2018) A lignin-epoxy resin derived from biomass as an alternative to formaldehyde-based wood adhesives. Green Chem 20(7):1459–1466. https://doi.org/10.1039/C7GC03026F
Liu G, Shi H, Kundu CK, Li Z, Li X, Zhang Z (2020) Preparation of novel biomass humate flame retardants and their flame retardancy in epoxy resin. J Appl Polym Sci 137(48):49601. https://doi.org/10.1002/app.49601
Miao J-T, Yuan L, Guan Q, Liang G, Gu A (2017) Biobased Heat Resistant Epoxy Resin with Extremely High Biomass Content from 2,5-Furandicarboxylic Acid and Eugenol. ACS Sustainable Chem Eng 5(8):7003–7011. https://doi.org/10.1021/acssuschemeng.7b01222
Puyou J, Yufeng M, Qinying K, Lulin X, Qiaoguang L, Yonghong Z (2020) Progress in development of epoxy resin systems based on biomass resources. Green Mater 8(1):6–23. https://doi.org/10.1680/jgrma.19.00026
Van Nieuwenhove I, Renders T, Lauwaert J, De Roo T, De Clercq J, Verberckmoes A (2020) Biobased Resins Using Lignin and Glyoxal. ACS Sustainable Chem Eng 8(51):18789–18809. https://doi.org/10.1021/acssuschemeng.0c07227
Qi M, Xu Y-J, Rao W-H, Luo X, Chen L, Wang Y-Z (2018) Epoxidized soybean oil cured with tannic acid for fully bio-based epoxy resin. RSC Adv 8(47):26948–26958. https://doi.org/10.1039/C8RA03874K
Hsu Y-I, Huang L, Asoh T-A, Uyama H (2020) Anhydride-cured epoxy resin reinforcing with citric acid-modified cellulose. Polym Degrad Stabil 178:109213. https://doi.org/10.1016/j.polymdegradstab.2020.109213
Zheng P, Chen N, Islam M, Ju SM, Liu L-K, Zhou J, Chen J, Zeng L, Lin H (2019) Development of Self-Cross-Linked Soy Adhesive by Enzyme Complex from Aspergillus niger for Production of All-Biomass Composite Materials. ACS Sustainable Chem Eng 7(4):3909–3916. https://doi.org/10.1021/acssuschemeng.8b04993
Xi X, Pizzi A, Lei H, Zhang B, Chen X, Du G (2022) Environmentally friendly chitosan adhesives for plywood bonding. Int J Adhes Adhes 112:103027. https://doi.org/10.1016/j.ijadhadh.2021.103027
Zeng G, Zhou Y, Liang Y, Zhang F, Luo J, Li J, Fang Z (2022) A hair fiber inspired bio-based adhesive with high bonding strength and mildew tolerance. Chem Eng J 434:134632. https://doi.org/10.1016/j.cej.2022.134632
Benchamas G, Huang G, Huang S, Huang H (2021) Preparation and biological activities of chitosan oligosaccharides. Trends Food Sci Tech 107:38–44. https://doi.org/10.1016/j.tifs.2020.11.027
Kou S, Peters LM, Mucalo MR (2021) Chitosan: A review of sources and preparation methods. Int J Biol Macromol 169:85–94. https://doi.org/10.1016/j.ijbiomac.2020.12.005
Muanprasat C, Chatsudthipong V (2017) Chitosan oligosaccharide: Biological activities and potential therapeutic applications. Pharmacol Therapeut 170:80–97. https://doi.org/10.1016/j.pharmthera.2016.10.013
Correia C, Soares da Costa D, Inácio AR, Vale AC, Peixoto D, Silva TH, Reis RL, Pashkuleva I, Alves NM (2022) Adhesive and Antibacterial Films Based on Marine-Derived Fucoidan and Chitosan. ACS Sustainable Chem Eng 10(50):16770–16779. https://doi.org/10.1021/acssuschemeng.2c05144
Roy S, Rhim J-W (2021) Fabrication of chitosan-based functional nanocomposite films: Effect of quercetin-loaded chitosan nanoparticles. Food Hydrocolloid 121:107065. https://doi.org/10.1016/j.foodhyd.2021.107065
Pal K, Bharti D, Sarkar P, Anis A, Kim D, Chałas R, Maksymiuk P, Stachurski P, Jarzębski M (2021) Selected Applications of Chitosan Composites. Int J Mol Sci 22(20):10968. https://doi.org/10.3390/ijms222010968
Li H, Hu C, Yu H, Chen C (2018) Chitosan composite scaffolds for articular cartilage defect repair: a review. RSC Adv 8(7):3736–3749. https://doi.org/10.1039/C7RA11593H
Wang W, Meng Q, Li Q, Liu J, Zhou M, Jin Z, Zhao K (2020) Chitosan Derivatives and Their Application in Biomedicine. Int J Mol Sci 21(2):487. https://doi.org/10.3390/ijms21020487
Francis AO, Zaini MAA, Muhammad IM, Abdulsalam S, El-Nafaty UA (2021) Physicochemical modification of chitosan adsorbent: a perspective. Biomass Convers Bior. https://doi.org/10.1007/s13399-021-01599-3
Wang J, Zhuang S (2022) Chitosan-based materials: Preparation, modification and application. J Clean Prod 355:131825. https://doi.org/10.1016/j.jclepro.2022.131825
Chen Q, Qi Y, Jiang Y, Quan W, Luo H, Wu K, Li S, Ouyang Q (2022) Progress in Research of Chitosan Chemical Modification Technologies and Their Applications. Mar Drugs 20(8):536. https://doi.org/10.3390/md20080536
Brasselet C, Pierre G, Dubessay P, Dols-Lafargue M, Coulon J, Maupeu J, Vallet-Courbin A, de Baynast H, Doco T, Michaud P, Delattre C (2019) Modification of Chitosan for the Generation of Functional Derivatives. Appl Sci 9(7):1321. https://doi.org/10.3390/app9071321
Ni K, Du G, Liu C, Wu Y, Yang H, Yin C, Su H, Ran X, Gao W, 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. https://doi.org/10.1016/j.cej.2023.142888
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 Sustainable Chem Eng 9(49):16849–16861. https://doi.org/10.1021/acssuschemeng.1c07012
Jin T, Zeng H, Huang Y, Liu L, Yao W, Lei H, Shi S, Du G, Zhang L (2023) Bio-hyperbranched polyesters synthesized from citric acid and bio-polyols and applications on wood adhesives. Polym Test 120:107974. https://doi.org/10.1016/j.polymertesting.2023.107974
Li C, Lei H, Wu Z, Xi X, Du G, Pizzi A (2022) Fully Biobased Adhesive from Glucose and Citric Acid for Plywood with High Performance. ACS Appl Mater Interfaces 14(20):23859–23867. https://doi.org/10.1021/acsami.2c02859
Ladeira NMB, Donnici CL, de Mesquita JP, Pereira FV (2021) Preparation and characterization of hydrogels obtained from chitosan and carboxymethyl chitosan. J Polym Res 28(9):335. https://doi.org/10.1007/s10965-021-02682-z
Barbosa HFG, Francisco DS, Ferreira APG, Cavalheiro ÉTG (2019) A new look towards the thermal decomposition of chitins and chitosans with different degrees of deacetylation by coupled TG-FTIR. Carbohyd Polym 225:115232. https://doi.org/10.1016/j.carbpol.2019.115232
Ravishankar K, Shelly KM, Desingh RP, Subramaniyam R, Narayanan A, Dhamodharan R (2018) Green, Solid-State Synthesis of Maleated Chitosan and Ionotropic Gelation with Chitosan. ACS Sustainable Chem Eng 6(11):15191–15200. https://doi.org/10.1021/acssuschemeng.8b03648
De Queiroz Antonino RS, Fook L, De Oliveira Lima BR, De Farias Rached VA, Lima R, Da Silva Lima EP, Peniche Covas RJ, Lia CA, Fook MV (2017) Preparation and Characterization of Chitosan Obtained from Shells of Shrimp (Litopenaeus vannamei Boone). Mar Drugs 15(5):141. https://doi.org/10.3390/md15050141
Wunderlich B (2003) Reversible crystallization and the rigid–amorphous phase in semicrystalline macromolecules. Prog Polym Sci 28(3):383–450. https://doi.org/10.1016/S0079-6700(02)00085-0
Jiang S, Niu H, Wang S, Qian Z, Du G, Zhou X, Shen Y, Yang Z, Li T (2023) Novel and high-performance tannin-polyamine adhesive: New insight into phenol-amine chemistry. Ind Crop Prod 192:116129. https://doi.org/10.1016/j.indcrop.2022.116129
Su M, Wu J, Pan P, Wang H (2022) Preparation and characterization of a water-resistant polyamide-oxidized starch-methyl methacrylate eco-friendly wood adhesive. Int J Bio Macromol 194:763–769. https://doi.org/10.1016/j.ijbiomac.2021.11.123
Zhang Q, Xu G, Pizzi A, Lei H, Xi X, Du G (2022) A Green Resin Wood Adhesive from Synthetic Polyamide Crosslinking with Glyoxal. Polymers 14(14):2819. https://doi.org/10.3390/polym14142819
Xu G, Zhang Q, Pizzi A, Lei H, Xi X, Du G (2022) Thermosetting environment-friendly polyamide adhesives prepared with citric acid and hexanediamine. J Appl Polym Sci 139(30):e52698. https://doi.org/10.1002/app.52698

Scheme 1 is available in the Supplementary Files section

No competing interests reported.

Scheme1.png

Download PDF

Version 1

posted

You are reading this latest preprint version

Boiling Water Resistant Fully Bio-Based Adhesive Made from Maleated Chitosan and Glucose with Excellent Performance

Status:

Version 1

Abstract

Figures

1 Introduction

2 Materials and methods

2.1 Materials

2.2 Preparation of CSC

2.3 Preparation of CSC-G adhesives

2.4 Fourier-transform infrared spectroscopy (FTIR) analysis

2.5 X-ray photoelectron spectroscopy (XPS) analysis

2.6 Thermal performance analysis

2.7 X-ray diffraction (XRD) analysis

2.8 Gel permeation chromatography (GPC) determinations

2.9 Test and analysis of adhesive properties

3 Results and discussion

3.1 Characterization results of CSC-G adhesive

4 Conclusions

Declarations

References

Scheme

Additional Declarations

Supplementary Files

Status:

Version 1