{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,26]],"date-time":"2026-03-26T04:09:25Z","timestamp":1774498165260,"version":"3.50.1"},"reference-count":35,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2024,11,11]],"date-time":"2024-11-11T00:00:00Z","timestamp":1731283200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["32071722"],"award-info":[{"award-number":["32071722"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Polymers"],"abstract":"<jats:p>Conventional adhesives used in wood-based panels typically contain volatile organic compounds, including formaldehyde, which can potentially lower indoor air quality and damage human health. Lignin, a natural adhesive present in wood, offers significant advantages over other materials due to its ready availability, renewable nature, rich aromatic rings, and aliphatic and aromatic hydroxyl groups, as well as quinone groups. However, when modified as an adhesive for wood-based panels, lignin suffers from poor water resistance and formaldehyde release. Dehydrogenation polymer (DHP), as a lignin model compound, possesses a structure similar to lignin and excellent water resistance, making it a potential substitute for lignin as a formaldehyde-free adhesive. A DHP-xylose complex was obtained from a condensation reaction between DHP and xylose in hemicellulose in a simulated hot-pressing environment. The feasibility of DHP bonding with hemicellulose components was verified using FT-IR and NMR spectroscopic methods. In addition, the structure of the adduct and condensation process were also studied. DHP and xylose underwent condensation under simulated hot-pressing conditions. Xylose and DHP may be linked by C-C bonds. The thermal condensation of DHP with xylose was investigated. This may contribute to a better understanding of the adhesive bonding process for xylose during hot-pressing and offer support for practical applications.<\/jats:p>","DOI":"10.3390\/polym16223139","type":"journal-article","created":{"date-parts":[[2024,11,11]],"date-time":"2024-11-11T08:46:54Z","timestamp":1731314814000},"page":"3139","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Thermal Condensation of Dehydrogenation Polymer (DHP) with Xylose"],"prefix":"10.3390","volume":"16","author":[{"given":"Peng","family":"Wang","sequence":"first","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jiaju","family":"Xie","sequence":"additional","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wenyao","family":"Peng","sequence":"additional","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-9306-6603","authenticated-orcid":false,"given":"Junxian","family":"Xie","sequence":"additional","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junjian","family":"An","sequence":"additional","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1513-0003","authenticated-orcid":false,"given":"Guangyan","family":"Zhang","sequence":"additional","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junjun","family":"Chen","sequence":"additional","affiliation":[{"name":"Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China"},{"name":"School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,11,11]]},"reference":[{"key":"ref_1","first-page":"6","article-title":"Discussions on the Developments of Aldehyde-Free Adhesive Technology and Aldehyde-Free Wood-based Panels in China","volume":"17","author":"Shen","year":"2022","journal-title":"Mod. Chem. Res."},{"key":"ref_2","first-page":"21","article-title":"Patent Analysis of Formaldehyde-free Adhesive for Wood-based Panels","volume":"S1","author":"Shi","year":"2022","journal-title":"Stand. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/S0960-8524(97)00030-8","article-title":"Effect of chemical modification of lignin on the gluebond performance of lignin-phenolic resins","volume":"60","author":"Freire","year":"1997","journal-title":"Bioresour. Technol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1016\/j.ijadhadh.2004.01.003","article-title":"Development and characterization of a wood adhesive using bagasse lignin","volume":"24","author":"Khan","year":"2004","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1002\/app.20887","article-title":"Use of a methylolated softwood ammonium lignosulfonate as partial substitute of phenol in resol resins manufacture","volume":"94","author":"Alonso","year":"2004","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_6","first-page":"38","article-title":"Study on Composite Adhesive of Hydroxymethylated Lignosulfonate\/Phenol-formaldehyde Resin with Low Free Formaldehyde","volume":"29","author":"Mu","year":"2009","journal-title":"Chem. Ind. For. Prod."},{"key":"ref_7","unstructured":"Mu, Y., Wang, C., Zhao, L., and Chun, F. (2008, January 12). Study on composite adhesive of alkali lignin\/phenol formaldehyde resin for E0 grade plywood. Proceedings of the Biorefining Technology Exchange and Industrialization Seminar and the 3rd National Chemical Application Technology Development Hot Spot Seminar, Xiamen, China."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1013","DOI":"10.1016\/j.biortech.2004.09.009","article-title":"Modification of ammonium lignosulfonate by phenolation for use in phenolic resins","volume":"96","author":"Alonso","year":"2005","journal-title":"Bioresour. Technol."},{"key":"ref_9","first-page":"678","article-title":"Phenolation Modification of Wheat Straw Soda Lignin and its Utilization in Preparation of Lignin-Based Phenolic Formaldehyde Resins Adhesive","volume":"21","author":"Liu","year":"2007","journal-title":"J. Chem. Eng. Chin. Univ."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1007\/s10973-004-6844-4","article-title":"Studies on thermal characterization of lignin: Substituted phenol formaldehyde resin as wood adhesives","volume":"89","author":"Khan","year":"2007","journal-title":"J. Therm. Anal. Calorim."},{"key":"ref_11","first-page":"36","article-title":"Application of Demethylated Lignosulfonate as a Substitute for Phenol in Wood Adhesives","volume":"3","author":"An","year":"1995","journal-title":"Chem. Ind. For. Prod."},{"key":"ref_12","first-page":"25","article-title":"Isolation of Lignin from Masson pine Kraft pulping black liqour and Preparation of Lignin-based Adhesives","volume":"26","author":"Guo","year":"1999","journal-title":"China For. Prod. Ind."},{"key":"ref_13","first-page":"361","article-title":"Enzymatic Modification of Lignin for Technical Use: Strategies and Results","volume":"27","author":"Milstein","year":"1989","journal-title":"ACS Symp. Ser."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1021\/bk-1989-0385.ch010","article-title":"Room-Temperature Curing Adhesives Based on Lignin and Phenoloxidases","volume":"385","author":"Haars","year":"1989","journal-title":"ACS Symp. Ser."},{"key":"ref_15","first-page":"13","article-title":"Effect of Laccase Treatment Conditions of Lignosulphonate on Shearing Strength of Plywood","volume":"34","author":"Cao","year":"2007","journal-title":"China For. Prod. Ind."},{"key":"ref_16","first-page":"185","article-title":"Bonding among woody fibers by use of enzymatic phenol dehydrogenative polymerization. Mechanism of generation of bonding strength","volume":"40","author":"Yamaguchi","year":"1994","journal-title":"Mokuzai Gakkaishi"},{"key":"ref_17","first-page":"931","article-title":"Applications of phenol dehydrogenative polymerization by laccase to bonding among woody-fibers","volume":"38","author":"Yamaguchi","year":"1992","journal-title":"Mokuzai Gakkaishi"},{"key":"ref_18","first-page":"220","article-title":"Application of phenol dehydrogenative polymerization of vanillic acid to bonding of woody fibers","volume":"37","author":"Yamaguchi","year":"1993","journal-title":"Mokuzai Gakkaishi"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"760","DOI":"10.1016\/S0141-0229(01)00339-8","article-title":"Wet strength improvement of unbleached kraft pulp through laccase catalyzed oxidation","volume":"28","author":"Lund","year":"2001","journal-title":"Enzym. Microb. Technol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"855","DOI":"10.1016\/S0141-0229(02)00020-0","article-title":"Evaluating laccase-facilitated coupling of phenolic acids to high-yield kraft pulps","volume":"30","author":"Chandra","year":"2002","journal-title":"Enzym. Microb. Technol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1021\/bp0300366","article-title":"Modification of high lignin content kraft pulps with laccase to improve paper strength properties. 1. Laccase treatment in the presence of gallic acid","volume":"20","author":"Chandra","year":"2004","journal-title":"Biotechnol. Prog."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1081\/WCT-120035945","article-title":"Improving laccase-facilitated grafting of 4-hydroxybenzoic acid to high-kappa kraft pulps","volume":"24","author":"Chandra","year":"2005","journal-title":"J. Wood Chem. Technol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7555","DOI":"10.1016\/j.biortech.2011.05.046","article-title":"Studying the effects of laccase-catalysed grafting of ferulic acid on sisal pulp fibers","volume":"102","author":"Aracri","year":"2011","journal-title":"Bioresour. Technol."},{"key":"ref_24","first-page":"16","article-title":"Modification of OCC Pulp by Laccase with the Phenols Contained in APMP Waste Liquor","volume":"26","author":"Zhang","year":"2011","journal-title":"Trans. China Pulp Pap."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1038\/197489a0","article-title":"A lignin carbohydrate bond as revealed by infra-red spectroscopy","volume":"197","author":"Bolker","year":"1963","journal-title":"Nature"},{"key":"ref_26","unstructured":"Wang, X. (2022). Study on Thermal Condensation Reaction Mechanism of Dehydrogenation Polymer Catalyzed with Acid. [Master\u2019s Thesis, Hubei University of Technology]."},{"key":"ref_27","first-page":"151","article-title":"New facile syntheses of monolignol glucosides; p-glucocoumaryl alcohol, coniferin and syringin","volume":"50","author":"Terashima","year":"1996","journal-title":"Holzforschung"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1039\/D0GC02463E","article-title":"A mechanistic study of cellulase adsorption onto lignin","volume":"23","author":"Yao","year":"2021","journal-title":"Green Chem."},{"key":"ref_29","first-page":"41","article-title":"Study on the Chemical Bond Connection between Lignin Dehydrogenation Polymer and Xylose","volume":"3","author":"Zhang","year":"2012","journal-title":"HuBei ZaoZhi"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"359","DOI":"10.3390\/ma6010359","article-title":"Recent Advances in Characterization of Lignin Polymer by Solution-State Nuclear Magnetic Resonance (NMR) Methodology","volume":"6","author":"Wen","year":"2013","journal-title":"Materials"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1515\/HF.2008.099","article-title":"Monolignol dehydrogenative polymerization in vitro in the presence of dioxane and a methylated \u03b2-\u03b2\u2032 dimer model compound","volume":"62","author":"Holmgren","year":"2008","journal-title":"Holzforschung"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1080\/17518253.2011.607852","article-title":"Efficient microwave-promoted synthesis of glucuronic and galacturonic acid derivatives using sulfuric acid impregnated on silica","volume":"5","author":"Richel","year":"2012","journal-title":"Green Chem. Lett. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5156","DOI":"10.1021\/acssuschemeng.7b00511","article-title":"Structural Insights on Recalcitrance during Hydrothermal Hemicellulose Extraction from Wood","volume":"5","author":"Nicola","year":"2017","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"136","DOI":"10.1007\/s10086-003-0543-9","article-title":"Formation and chemical structures of acid-soluble lignin II: Reaction of aromatic nuclei model compounds with xylan in the presence of a counterpart for condensation, and behavior of lignin model compounds with guaiacyl and syringyl nuclei in 72% sulfuric acid","volume":"50","author":"Matsushita","year":"2004","journal-title":"J. Wood Sci."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"418","DOI":"10.1515\/hfsg.1995.49.5.418","article-title":"Chemical Structures of Sulfuric Acid Lignin. Part XII. Reaction of Lignin Models with Carbohydrates in 72% H2SO4","volume":"49","author":"Yasuda","year":"1995","journal-title":"Holzforschung"}],"container-title":["Polymers"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4360\/16\/22\/3139\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:29:56Z","timestamp":1760113796000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4360\/16\/22\/3139"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,11]]},"references-count":35,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2024,11]]}},"alternative-id":["polym16223139"],"URL":"https:\/\/doi.org\/10.3390\/polym16223139","relation":{},"ISSN":["2073-4360"],"issn-type":[{"value":"2073-4360","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,11]]}}}