{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T09:17:12Z","timestamp":1775899032055,"version":"3.50.1"},"reference-count":47,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2022,12,5]],"date-time":"2022-12-05T00:00:00Z","timestamp":1670198400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000780","name":"European Regional Development Fund (ERDF)","doi-asserted-by":"publisher","award":["21874"],"award-info":[{"award-number":["21874"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Regional Development Fund (ERDF)","doi-asserted-by":"publisher","award":["UIDB\/50011\/2020"],"award-info":[{"award-number":["UIDB\/50011\/2020"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Regional Development Fund (ERDF)","doi-asserted-by":"publisher","award":["UIDP\/50011\/2020"],"award-info":[{"award-number":["UIDP\/50011\/2020"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Regional Development Fund (ERDF)","doi-asserted-by":"publisher","award":["LA\/P\/0006\/2020"],"award-info":[{"award-number":["LA\/P\/0006\/2020"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"name":"FCT\/MEC (PIDDAC)","award":["21874"],"award-info":[{"award-number":["21874"]}]},{"name":"FCT\/MEC (PIDDAC)","award":["UIDB\/50011\/2020"],"award-info":[{"award-number":["UIDB\/50011\/2020"]}]},{"name":"FCT\/MEC (PIDDAC)","award":["UIDP\/50011\/2020"],"award-info":[{"award-number":["UIDP\/50011\/2020"]}]},{"name":"FCT\/MEC (PIDDAC)","award":["LA\/P\/0006\/2020"],"award-info":[{"award-number":["LA\/P\/0006\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Polymers"],"abstract":"<jats:p>Lignin-based polyol was obtained via oxyalkylation reaction with propylene carbonate using eucalyptus kraft lignin isolated from the industrial cooking liquor by the Lignoboost\u00ae procedure. This lignin-based polyol (LBP) was used without purification in the preparation of polyurethane (PU) adhesives combined with polymeric 4,4\u2032-methylenediphenyl diisocyanate (pMDI). A series of adhesives were obtained by varying the NCO\/OH ratio of PU counterparts (pMDI and LBPs) and their performance was evaluated by gluing wood pieces under predefined conditions. The adhesion properties of the novel PU adhesive were compared with those of a commercial PU adhesive (CPA). The occurrence and extent of curing reactions and changes in the polymeric network of PA were monitored by Fourier transform infrared spectroscopy (FTIR) and dynamic mechanical analysis. Although the lap shear strength and glass transition temperature of the lignin-based PU adhesives have increased steadily with the NCO\/OH ratio ranging from 1.1\u20132.2, chemical aging resistance can be compromised when the NCO\/OH is very low. It was found that the lignin-based PU adhesive with an NCO\/OH ratio of 1.3 showed better chemical resistance and adhesion efficiency than CPA possibly because the NCO\/OH in the latter is too high as revealed by FTIR spectroscopy. Despite some lower thermal stability and shorter gelation time of lignin-based PU than CPA, the former revealed great potential to reduce the use of petroleum-derived polyols and isocyanates with potential application in the furniture industry as wood bonding adhesive.<\/jats:p>","DOI":"10.3390\/polym14235305","type":"journal-article","created":{"date-parts":[[2022,12,5]],"date-time":"2022-12-05T05:31:32Z","timestamp":1670218292000},"page":"5305","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Polyurethane Adhesives Based on Oxyalkylated Kraft Lignin"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3017-8462","authenticated-orcid":false,"given":"Fernanda Rosa","family":"Vieira","sequence":"first","affiliation":[{"name":"Department of Chemistry, CICECO-Institute of Materials, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1865-098X","authenticated-orcid":false,"given":"Nuno","family":"Gama","sequence":"additional","affiliation":[{"name":"Department of Chemistry, CICECO-Institute of Materials, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4518-5718","authenticated-orcid":false,"given":"Sandra","family":"Magina","sequence":"additional","affiliation":[{"name":"Department of Chemistry, CICECO-Institute of Materials, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6462-8679","authenticated-orcid":false,"given":"Ana","family":"Barros-Timmons","sequence":"additional","affiliation":[{"name":"Department of Chemistry, CICECO-Institute of Materials, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6304-5105","authenticated-orcid":false,"given":"Dmitry V.","family":"Evtuguin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, CICECO-Institute of Materials, Campus de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1561-4406","authenticated-orcid":false,"given":"Paula C. O. R.","family":"Pinto","sequence":"additional","affiliation":[{"name":"RAIZ, Forest and Paper Research Institute, Quinta de S. Francisco, 3801-501 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,5]]},"reference":[{"key":"ref_1","unstructured":"Market, W. (2022, September 02). Adhesive No Title. Available online: https:\/\/www.grandviewresearch.com\/industry-analysis\/wood-adhesives-market."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.ijadhadh.2019.04.007","article-title":"Technological performance of formaldehyde-free adhesive alternatives for particleboard industry","volume":"94","author":"Solt","year":"2019","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"107603","DOI":"10.1016\/j.buildenv.2021.107603","article-title":"Networking human biomarker and hazardous chemical elements from building materials: Systematic literature review and in vivo test","volume":"192","author":"Cho","year":"2021","journal-title":"Build Environ."},{"key":"ref_4","first-page":"10.1","article-title":"Adhesives with Wood Materials- Bond Formation and Performance","volume":"190","author":"Frihart","year":"2010","journal-title":"Wood Handb. Wood Eng. Mater."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.ijadhadh.2004.04.003","article-title":"Polyurethane resin-based adhesives: Curing reaction and properties of cured systems","volume":"25","author":"Malucelli","year":"2005","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Segura, D.M., Nurse, A.D., Mccourt, A., Phelps, R., and Segura, A. (2005). Chemistry of Polyurethane Adhesives and Sealants. Handbook of Adhesives and Sealants, Elsevier Science Ltd.","DOI":"10.1016\/S1874-5695(02)80004-5"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1266","DOI":"10.1016\/j.progpolymsci.2013.11.004","article-title":"Chemical modification of lignins: Towards biobased polymers","volume":"39","author":"Laurichesse","year":"2014","journal-title":"Prog. Polym. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3008","DOI":"10.1002\/app.28393","article-title":"Lignins as Macromonomers for Polyurethane Synthesis: A Comparative Study on Hydroxyl Group Determination","volume":"109","author":"Cateto","year":"2008","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_9","first-page":"53","article-title":"The LignoBoost process","volume":"44","author":"Tomani","year":"2010","journal-title":"Cellul Chem. Technol."},{"key":"ref_10","first-page":"18","article-title":"The LignoForce SystemTM: A new process for the production of high-quality lignin from black liquor","volume":"115","author":"Kouisni","year":"2014","journal-title":"Pulp Pap. Can."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.indcrop.2018.03.006","article-title":"A simple methodology for improving the performance and sustainability of rigid polyurethane foam by incorporating industrial lignin","volume":"117","author":"Hayati","year":"2018","journal-title":"Ind. Crops Prod."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1470","DOI":"10.1007\/s10853-017-1562-z","article-title":"Thermal and mechanical properties of coconut shell lignin-based polyurethanes synthesized by solvent-free polymerization","volume":"53","author":"Avelino","year":"2017","journal-title":"J. Mater. Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"8816","DOI":"10.1021\/acssuschemeng.8b01170","article-title":"Biobased Structurally Compatible Polymer Blends Based on Lignin and Thermoplastic Elastomer Polyurethane as Carbon Fiber Precursors","volume":"6","author":"Culebras","year":"2018","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/1754-6834-6-12","article-title":"Effect of replacing polyol by organosolv and kraft lignin on the property and structure of rigid polyurethane foam","volume":"6","author":"Pan","year":"2013","journal-title":"Biotechnol. Biofuels"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/BF00258264","article-title":"Engineering plastics from lignin","volume":"12","author":"Glasser","year":"1984","journal-title":"Polym. Bull."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2583","DOI":"10.1021\/ie801251r","article-title":"Optimization study of lignin oxypropylation in view of the preparation of polyurethane rigid foams","volume":"48","author":"Cateto","year":"2009","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.1002\/mame.200500200","article-title":"Oxypropylation of Lignins and Preparation of Rigid Polyurethane Foams from the Ensuing Polyols","volume":"290","author":"Belgacem","year":"2005","journal-title":"Macromol. Mater. Eng."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Shojaei Saadi, H.A. (2014). Propylene Oxide. Encycl. Toxicol., 1117\u20131119.","DOI":"10.1016\/B978-0-12-386454-3.00644-8"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.reactfunctpolym.2017.09.011","article-title":"Comparison of different cyclic organic carbonates in the oxyalkylation of various types of lignin","volume":"120","author":"Saake","year":"2017","journal-title":"React. Funct. Polym."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Xuefeng, Z., Kim, Y., Islam, E., Taylor, M., and Eberhardt, T.L. (2019). Rigid polyurethane foams containing lignin oxyalkylated with ethylene carbonate and polyethylene glycol. Ind. Crops Prod., 141.","DOI":"10.1016\/j.indcrop.2019.111797"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"100793","DOI":"10.1016\/j.mtchem.2022.100793","article-title":"Scalable single-step synthesis of lignin-based liquid polyols with ethylene carbonate for polyurethane foams","volume":"24","author":"Duval","year":"2022","journal-title":"Mater. Today Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"10505","DOI":"10.1021\/jf202452m","article-title":"Preparation of Lignopolyols from Wheat Straw Soda Lignin","volume":"59","author":"Ahvazi","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Vieira, F.R., Barros-timmons, A., Evtuguin, D.V., and Pinto, P.C.O.R. (2022). Oxyalkylation of LignoboostTM Kraft Lignin with Propylene Carbonate: Design of Experiments towards Synthesis Optimization. Materials, 15.","DOI":"10.3390\/ma15051925"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"927","DOI":"10.3144\/expresspolymlett.2016.86","article-title":"Bio-based polyurethane prepared from Kraft lignin and modified castor oil","volume":"10","author":"Tavares","year":"2016","journal-title":"Express Polym. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7072","DOI":"10.3390\/ma14227072","article-title":"Lignosulfonate-Based Polyurethane Adhesives","volume":"14","author":"Evtuguin","year":"2021","journal-title":"Materials"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1080\/00218464.2016.1177793","article-title":"Effects of NCO:OH ratio on the mechanical properties and chemical structure of Kraft lignin\u2014Based polyurethane adhesive","volume":"93","author":"Nacas","year":"2017","journal-title":"J. Adhes."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1423","DOI":"10.1080\/00218464.2020.1784148","article-title":"Kraft lignin-containing polyurethane adhesives: The role of hydroxypropylation on thermomechanical properties","volume":"97","author":"Gouveia","year":"2021","journal-title":"J. Adhes."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/app.52477","article-title":"Polyurethane adhesives from castor oil and modified lignin via reaction with propylene carbonate","volume":"139","author":"Antonino","year":"2022","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1515\/hf-2019-0274","article-title":"Effect of different catalysts on the oxyalkylation of eucalyptus Lignoboost\u00ae kraft lignin","volume":"74","author":"Vieira","year":"2020","journal-title":"Holzforschung"},{"key":"ref_30","unstructured":"(2004). Standard Test Method for Strength Properties of Adhesives in Plywood Type Construction in Shear by Tension Loading (Standard No. ASTM D906)."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1016\/S0143-7496(03)00044-7","article-title":"Castor oil based polyurethane adhesives for wood-to-wood bonding","volume":"23","author":"Somani","year":"2003","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1016\/j.ijadhadh.2011.05.004","article-title":"Characterization of canola oil based polyurethane wood adhesives","volume":"31","author":"Kong","year":"2011","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_33","unstructured":"Frihart, C.R. (2005). Wood Adhesion and Adhesives. Handbook of Wood Chemistry and Wood Composites, CRC Press."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"796","DOI":"10.15376\/biores.14.1.796-815","article-title":"Characterization of polyurethane wood adhesive prepared from liquefied sawdust by ethylene carbonate","volume":"14","author":"Daneshvar","year":"2019","journal-title":"BioResources"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Puszka, A., and Sikora, J.W. (2022). Synthesis and Characterization of New Polycarbonate-Based Poly(thiourethane-urethane)s. Polymers, 14.","DOI":"10.3390\/polym14142933"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"102413","DOI":"10.1016\/j.ijadhadh.2019.102413","article-title":"Cure and performance of castor oil polyurethane adhesive","volume":"95","author":"Gama","year":"2019","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1020","DOI":"10.1080\/01694243.2014.883772","article-title":"Polyurethane wood adhesive from palm oil-based polyester polyol","volume":"28","year":"2014","journal-title":"J. Adhes. Sci. Technol."},{"key":"ref_38","first-page":"2658","article-title":"Synthesis and Properties of Multihydroxy Soybean Oil from Soybean Oil and Polymeric Methylene-Diphenyl- 4,4-Diisocyanate\/Multihydroxy Soybean Oil Polyurethane Adhesive to Wood","volume":"116","author":"Choi","year":"2011","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1016\/S0143-7496(03)00070-8","article-title":"Polyurethane adhesive system from biomaterial-based polyol for bonding wood","volume":"23","author":"Desai","year":"2003","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"124164","DOI":"10.1016\/j.colsurfa.2019.124164","article-title":"Signally improvement of polyurethane adhesive with hydroxy-enriched lignin from bagasse","volume":"585","author":"Chen","year":"2020","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"102427","DOI":"10.1016\/j.ijadhadh.2019.102427","article-title":"Synthesis and characterization of lignin-polyurethane based wood adhesive","volume":"95","author":"Gadhave","year":"2019","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3672","DOI":"10.3390\/ijerph8093672","article-title":"Environmental isocyanate-induced asthma: Morphologic and pathogenetic aspects of an increasing occupational disease","volume":"8","author":"Bartsch","year":"2011","journal-title":"Int. J. Environ. Res. Public Health"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"872","DOI":"10.1093\/annweh\/wxx052","article-title":"Effects of known determinants on methylene bisphenyl isocyanate (MDI) concentration during spray-on truck bed-lining processes","volume":"61","author":"Schaal","year":"2017","journal-title":"Ann. Work Expo. Health"},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Puszka, A. (2018). Thermal and mechanical behavior of new transparent thermoplastic polyurethane elastomers derived from cycloaliphatic diisocyanate. Polymers, 10.","DOI":"10.3390\/polym10050537"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1937","DOI":"10.1002\/pat.4083","article-title":"The influence of soft segments on some properties of new transparent segmented polyurethanes","volume":"28","author":"Puszka","year":"2017","journal-title":"Polym. Adv. Technol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/j.polymertesting.2017.05.042","article-title":"Sound absorption properties of polyurethane foams derived from crude glycerol and liquefied coffee grounds polyol","volume":"62","author":"Gama","year":"2017","journal-title":"Polym. Test"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/j.indcrop.2014.05.038","article-title":"Synthesis and characterization of Jatropha (Jatropha curcas L.) oil-based polyurethane wood adhesive","volume":"60","author":"Aung","year":"2014","journal-title":"Ind. Crops Prod."}],"container-title":["Polymers"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4360\/14\/23\/5305\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:33:59Z","timestamp":1760146439000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4360\/14\/23\/5305"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,5]]},"references-count":47,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["polym14235305"],"URL":"https:\/\/doi.org\/10.3390\/polym14235305","relation":{},"ISSN":["2073-4360"],"issn-type":[{"value":"2073-4360","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,5]]}}}