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Preparation of Environmentally Friendly Urea-Hexanediamine-Glyoxal(HUG)Resin Wood Adhesive

Journal of Renewable Materials 2024年第2期12卷 235-244页

作者： Qianyu Zhang Shi Chen Long Cao Hong Lei Antonio Pizzi xuedong xi Guanben Du Yunnan Key Laboratory of Wood Adhesives and Glue Products College of Material Science and EngineeringSouthwest Forestry UniversityKunming650224China International Joint Research Center for Biomass Materials Southwest Forestry UniversityKunming650224China College of Chemical and Materials Engineering Zhejiang A&F UniversityHangzhou311300China LERMAB University of LorraineEpinal88000France

Using non-toxic,low-volatile glyoxal to completely replace formaldehyde for preparing urea-glyoxal(UG)resin adhesive is a hot research topic that could be of great interest for the wood industry.However,urea-glyoxal(UG)resins prepared by just using glyoxal instead of formaldehyde usually yields a lower degree of polymerization.This results in a poorer bonding performance and water resistance of UG resins.A good solution is to pre-react urea to preform polyurea molecules presenting already a certain degree of polymerization,and then to condense these with glyoxal to obtain a novel UG resin.Therefore,in this present work,the urea was reacted with hexamethylene diamine to form a polyurea named HU,and then this was used to react it with different amounts of glyoxal to synthesize hexamethylenediamine-urea-glyoxal(HUG)polycondensation resins,and to use this for bonding plywood.The results show that the glyoxal can well react with HU polyuria via addition and schiff base reaction,and also the HUG resin exhibits excellent bonding strength and water resistance.The shear strength of the plywood bonded with this HUG at 160°C hot press temperature as high as 1.93 MPa,2.16 MPa and 1.61 MPa,respectively,which meets the requirement of the China national standard GB/T 9846-2015(≥0.7 MPa),and can be a good choice as a wood adhesive for industrial application.

关键词： Urea-glyoxal resin hexamethylene diamine wood adhesives water resistance

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Crosslinking Mechanism of Soy Protein-based Adhesives based on Glyoxal and a Compound of Protein Model

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Journal of Wuhan University of Technology(Materials Science) 2023年第4期38卷 942-950页

作者：曹龙 LIANG Jiankun ZHANG Qiaoyan xi xuedong 吴志刚雷洪 Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products Southwest Forestry UniversityKunming650224China College of Civil Engineering Kaili UniversityQiandongnanKaili556011China Zhazuo State-owned Forest Farm Guiyang550299China College of Forestry Guizhou UniversityGuiyang550025China School of Chemistry Materials Engineering Zhejiang A&F UniversityHangzhou311300China

The crosslinking mechanism of glyoxal and asparagine was analyzed,and the relationship between the mechanism and practical performances of soy protein-based adhesives was also discussed.It is shown that when pH=1 and 3,glyoxal reacted with asparagine in the form of major cyclic ether compounds.When pH=5,glyoxal reacted with asparagine in two structural forms of sodium glycollate and cyclic ether compounds.However,amidogens of asparagine were easy to develop protonation under acid conditions.Supplemented by the instability of cyclic ether compounds,the reaction activity and reaction degree between glyoxal and asparagine were relatively small.Under alkaline conditions,glyoxal mainly reacted with asparagine in the form of sodium glycollate.With the increase of pH,the polycondensation was more sufficient and the produced polycondensation products were more stable.The reaction mechanism between glyoxal and asparagine had strong correspondence to the practical performances of the adhesives.Glyoxal solution could develop crosslinking reactions with soy protein under both acid and alkaline conditions.Bonding strength and water resistance of the prepared soy protein-based adhesives were increased significantly.When pH>7,glyoxal had relatively high reaction activity and reaction intensity with soy protein,and the prepared adhesives had high crosslinking density and cohesion strength,showing relatively high bonding strength,water resistance and thermal stability.

关键词： soy protein wood adhesives glyoxal model compounds crosslinking

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MUF Resins Improved by Citric Acid as Adhesives for Wood Veneer Panels

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Journal of Renewable Materials 2023年第2期11卷 539-553页

作者： Claudio Del Menezzi Antonio Pizzi Siham Amirou xuedong xi Department of Forestry Engineering Faculty of TechnologyUniversity of BrasiliaBrasíliaBrazil LERMAB University of LorraineNancyFrance SeniorPost-Doctoral Internship LERMAB-ENSTIBUniversity of LorraineEpinalFrance Yunnan Key Laboratory of Wood Adhesives and Glue Products College of Material Science and EngineeringSouthwest Forestry UniversityKunmingChina International Joint Research Center for Biomass Materials Southwest Forestry UniversityKunmingChina

This article presents the first applied results of using citric acid in combinations with a melamine-urea-formal-dehyde(MUF)resin for bonding wood veneers.The chemical reactions involved are shown based on a MALDI ToF analysis of the reaction of the MUF resin with citric acid.The preliminary results of the physical and mechanical properties of the LVL prepared are also presented.Veneers from Populus sp were used to manufacture 5-layer laminated veneer lumber(LVL)of small dimensions.Five combinations of the amount of citric acid,MUF spread rate and pressing parameters were tested.LVL bonded with 20%of citric acid+100 g/m^(2)of MUF,hot-pressed using a 3-step process with maximum 1.5 MPa of pressure yielded the board with better dimensional stability and mechanical properties.It could be concluded that citric acid in combination with MUF can be used for bonding wood veneer and the research should be continued to study further the parameters involved and to enhance the results.

关键词： LVL wood adhesives citric acid MUF resins MALDI ToF mechanical performance

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MALDI ToF Investigation of the Reaction of Soy Protein Isolate with Glutaraldehyde for Wood Adhesives

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Journal of Renewable Materials 2023年第3期11卷 1439-1450页

作者： Qianyu Zhang Antonio Pizzi Hong Lei xuedong xi Ming Cao Long Cao Yunnan key Laboratory of Wood Adhesives and Glue Products College of Material Science and EngineeringSouthwest Forestry UniversityKunming650224China International Joint Research Center for Biomass Materials Southwest Forestry UniversityKunming650224China Universitéde Lorraine LERMAB-ENSTIB 27 rue Philippe SeguinEpinal88000France

Soy protein adhesives are currently a hot research topic in the wood panels industry for the abundant raw material reserves,reasonable price and outstanding environmental features.But their poor water resistance,low bonding strength and intolerance to mold are major drawbacks,so that proper modification before use is essential.Glutaraldehyde is one of the more apt cross-linking agents for soybean protein adhesives,which can effectively improve the bonding strength and water resistance of the adhesive.Equally,glutaraldehyde is also an efficient and broad-spectrum fungicide that can significantly improve the anti-fungal properties of a soy protein adhesive.In the work presented here,matrix assisted laser desorption ionization(MALDI-ToF)mass spectrometry and Fourier transform infrared spectroscopy techniques were used to analyze the reaction mechanism of glutaraldehyde cross-linking soybean protein.The results confirmed the reaction of the aldehyde group with amino groups of the side chains and the amide groups of the peptide linkages constituting the skeletal chain of the protein.The laboratory plywood and particleboard bonded with glutaraldehyde-soy bean protein adhesives were prepared to determine the adhesive bonding properties,the dry strength,24 h cold water soaking wet strength and 3 h hot water(63°C)wet strength of plywood were 2.03,1.13 and 0.75 MPa,respectively,which satisfied the requirements of industrial production.

关键词： Bio-based adhesives soy bean protein MALDI-ToF particleboard plywood

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No-Aldehydes Glucose/Sucrose-Triacetin-Diamine Wood Adhesives for Particleboard

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Journal of Renewable Materials 2020年第7期8卷 715-725页

作者： xuedong xi Antonio Pizzi LERMAB-ENSTIB University of LorraineEpinal88000France

A three reagents adhesive system for wood particleboards not containing any aldehyde was developed by the reaction of glucose or sucrose with triacetin(glycerin triacetate)and with hexamethylene diamine.The system was found to be based on the mix of three reactions,namely the reaction of(i)glucose with triacetin,(ii)of the diamine with triacetin,and(iii)of glucose with the diamine.The chemical species formed were identified by Matrix Assisted Laser Desorption Ionization Time of Flight(MALDI-ToF)mass spectrometry.Wood particleboard panels were prepared with this adhesive system and gave good internal bond(IB)strength results suitable for interior grade panels and with extremely low formaldehyde emission.

关键词： No-formaldehyde adhesive no-aldehyde adhesive monosaccharidetriacetin-hexamethylene diamine glucose sucrose wood adhesive particleboard MALDI

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Glucose-Biobased Non-Isocyanate Polyurethane Rigid Foams

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Journal of Renewable Materials 2019年第3期7卷 301-312页

作者： xuedong xi A.Pizzi C.Gerardin Guanben Du LERMAB-ENSTIB University of LorraineEpinalFrance Southwest Forestry University KunmingYunnanChina LERMAB Faculty of SciencesUniversity of LorraineNancyFrance

Glucose-based non-isocyanate polyurethanes(NIPU)were prepared by reaction of glucose with dimethyl carbonate and hexamethylene diamine.These were used to prepare partially biobased polyurethane foams by reaction with NaHCO3 as a blowing agent and addition of a silane coupling agent having different functions such as coreactant and adjuvant to obtain more uniform and smaller cells.The foams were foamed and hardened by applying heat.The foams presented very limited fire resistance indicating that as for synthetic polyurethane foams the eventual use of a fire retardant appears to be necessary.The 2 hours water absorption was used to indicate if close cells or open cells occur.More characteristic is their stress strain behaviour.While compression does indeed flatten the cell walls nonetheless the cellular structure is maintained and the cell walls have not been destroyed.This indicates a certain level of elasticity in the cell walls of formulations containing NaHCO3.In effect the macro-appearance of this foams,confirms this explanation as the foam is densified and holds together.

关键词： Polyurethane biofoams non-isocyanate polyurethanes NIPU biofoams glucose

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Effects of Steam Heat-Treatment on Properties of Pinus massoniana Wood and Its Bonding Performance

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Journal of Renewable Materials 2021年第4期9卷 789-801页

作者： Meifen Tian Bengang Zhang Zhigang Wu Liping Yu Lifen Li xuedong xi College of Forestry Guizhou UniversityGuiyang550025China Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products Southwest Forestry UniversityKunming650224China ENSTIB-LERMAB University of LorraineEpinal88051France

Pinus massoniana wood was modified by steam heat-treatment at 160℃,180℃,200℃ and 220℃ respectively and effects of the changes of density,pH,surface wettability and apparent morphology of Pinus massoniana heat-treated wood on its bonding performance were studied in this paper.The results showed that Pinus massoniana wood underwent a series of physical and chemical changes during heat-treatment as the the following:(1)The degradation of hemicellulose and cellulose with low degree of polymerization,degradation and migration of the extract resulting in the decline of density and pH of heat-treated Pinus massoniana wood.(2)Brittle fracture occured on the cell wall surface,and the pit collapse,shrink and deformation,resulting in the formation of roughness and porosity on the wood surface.(3)The surface energy decreased with the improvement of temperature,the surface wettability of Pinus massoniana wood treated at 160℃–180℃ was good,while that at 200℃–220℃ showed hydrophobicity.(4)Changes of density,pH,surface roughness and porosity,and wettability resulted in a reduction in the bonding strength and reliability of heat-treated Pinus massoniana wood with MUF resin adhesive.(5)When the temperature was at 160℃–180℃,the better wettability of heat-treated Pinus massoniana wood could guarantee the better bonding performance.

关键词： Pinus massoniana wood heat-treatment bonding performance

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Study on the Soy Protein-Based Adhesive Cross-Linked by Glyoxal

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Journal of Renewable Materials 2021年第2期9卷 205-218页

作者： Zhigang Wu Jiankun Liang Hong Lei Bengang Zhang xuedong xi Lifen Li Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products Southwest Forestry UniversityKunming650224China College of Forestry Guizhou UniversityGuiyang550025China Kaili University Qiandongnan556011China

Based on the ESI-MS and ^(13)C-NMR analysis of the forms of glyoxal in acidic and alkaline solutions,the soy-based adhesive cross-linked by glyoxal was prepared in this work.The results showed that glyoxal existed in water in different forms at different pH levels.Under alkaline conditions,glyoxal transformed to glycolate through the intramolecular disproportionation reaction.Under acidic conditions,although some of glyoxal transformed to glycolate as what happened under alkaline conditions,most of glyoxal molecules existed in the form of fiveor six-membered cyclic ether structure.No ethylene tetraol or free aldehyde group was actually detected under these conditions.Although glyoxal reacted with soy protein under both acidic and alkaline conditions,alkaline conditions were more favorable for the improvement of mechanical performance and water resistance of soybased adhesives than acid conditions.

关键词： Glyoxal soy protein-based adhesive cross-link

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Study of Burning Behaviors and Fire Risk of Flame Retardant Plywood by Cone Calorimeter and TG Test

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Journal of Renewable Materials 2021年第12期9卷 2143-2157页

作者： Liping Yu Zhongyou Luo Lifen Li xuedong xi Zhigang Wu Bengang Zhang College of Forestry Guizhou UniversityGuiyang550025China Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products Southwest Forestry UniversityKunming650224China ENSTIB-LERMAB University of LorraineEpinal88051France IUT-LERMAB University of LorraineEpinal88000France

A flame retardant composition was prepared by using phosphoguanidine,guanidine sulfamate,disodium octaborate tetrahydrate and dodecyl dimethyl benzyl ammonium chloride.Veneers were immersed in such flame retardant mixture to prepare plywood.The combustion characteristics and thermal stability of plywood were assessed using a cone calorimeter and TG.Results showed that:(1)High concentration and loading of flame retardant were beneficial for the fire resistance of the plywood.(2)The limiting oxygen index(LOI)and residual mass of plywood processed using the flame retardant was increased by 87.52%and 58.66%compared to those of the untreated plywood,while the average heat release rate(av-HRR),total heat release(THR),effective heat of combustion(EHC),total smoke release(TSR),CO yield(COY),CO_(2) yield(CO_(2)Y)and oxygen consumption were decreased by 44.3%,82.9%,47.0%,86.0%,89.9%,50.1%and 83.1%,respectively.(3)Treated plywood which had a low fire growth index(FGI)displayed a later combustion heat release rate peak and slower flame spread than observed for the untreated material.Combustion of treated plywood displayed a higher fire performance index(FPI),indicating a longer time to ignition.This suggests that burning structures from this material would be subject to a longer time for escape from the structure and would present lower fire risk than similar structures containing treated plywood.(4)TG results demonstrated that the presence of the flame retardant can decrease the pyrolysis temperature for hemicellulose and cellulose,change the decomposition and reaction progress for plywood degradation and promote dehydration carbonization and accelerated charformation.Moreover,the formed char was more stable than that combustion of untreated plywood.(5)The flame retardant contains nitrogen(N),phosphorus(P),boron(B),chlorine(Cl)and guanidine(Gu)compounds.The adhesive also contains N and P compounds.These substances display flame resistance and supplement each other to generate flame retardance than any one used alone.By chan

关键词： Flame retardant plywood cone calorimeter burning behaviors fire risk

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Soy Protein Isolate Non-Isocyanates Polyurethanes(NIPU)Wood Adhesives

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Journal of Renewable Materials 2021年第6期9卷 1045-1057页

作者： xinyi Chen Antonio Pizzi xuedong xi xiaojian Zhou Emmanuel Fredon Christine Gerardin LERMAB University of LorraineEpinal88000France Yunnan Key Laboratory of Wood Adhesives and Glue Products Southwest Forestry UniversityKunming650224China LERMAB University of LorraineNancy54000France

Soy-protein isolate(SPI)was used to prepare non-isocyanate polyurethane(NIPU)thermosetting adhesives for wood panels by reacting it with dimethyl carbonate(DMC)and hexamethylene diamine.Both linear as well as branched oligomers were obtained and identified,indicating how such oligomer structures could further cross-link to form a hardened network.Unusual structures were observed,namely carbamic acid-derived urethane linkages coupled with lactam structures.The curing of the adhesive was followed by thermomechanical analysis(TMA).It appeared to follow a two stages process:First,at a lower temperature(maximum 130℃),the growth of linear oligomers occurred,finally forming a physically entangled network.This appeared to collapse and disentangle,causing a decrease of MOE,as the temperature increases.This appears to be due to the ever more marked Brownian movements of the linear oligomer chains with the increase of the temperature.Second,chemical cross-linking of the chains appeared to ensue,forming a hardened network.This was shown by the thermomechanical analysis(TMA)showing two distinct MOE maxima peaks,one around 130℃ and the other around 220℃,with a very marked MOE decrease between the two.Plywood panels were prepared and bonded with the SPI-NIPU wood adhesive and the results obtained are presented.The adhesive appeared to pass comfortably the requirements for dry strength of relevant standards,showing to be suitable for interior grade plywood panels.It did not pass the requirements for wet tests.However,addition of 15%of glycerol diglycidyl ether improved the wet tests results but still not enough to satisfy the standards requirements.

关键词： Bio-based wood adhesives soy protein isolate non-isocyanate polyurethanes(NIPU) wood panels MALDI ToF

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