{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,3]],"date-time":"2026-03-03T07:51:23Z","timestamp":1772524283516,"version":"3.50.1"},"reference-count":24,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2019,2,19]],"date-time":"2019-02-19T00:00:00Z","timestamp":1550534400000},"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":["31660176"],"award-info":[{"award-number":["31660176"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["31800481"],"award-info":[{"award-number":["31800481"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Science-technology Support Foundation of Guizhou Province of China","award":["[2019]2325"],"award-info":[{"award-number":["[2019]2325"]}]},{"name":"Science-technology Support Foundation of Guizhou Province of China","award":["[2019]2308"],"award-info":[{"award-number":["[2019]2308"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Polymers"],"abstract":"<jats:p>To find the effects of cross-linker phenol-formaldehyde (PF) resin on the performance of soy-based adhesives, the reaction between model compounds hydroxymethyl phenol (HPF) and glutamic acid were studied in this paper. HPF prepared in laboratory conditions showed higher content of hydroxymethyl groups than normal PF resin, which was proved by the results of Electrospray Ionization Mass Spectrometry (ESI-MS) and 13C Nuclear Magnetic Resonance (13C-NMR). The results of ESI-MS, Fourier transform infrared spectroscopy (FT-IR), and 13C-NMR based on resultant products obtained from model compounds showed better water resistance of the soy protein-based adhesive modified by PF-based resin, which indicated the reaction between PF resin and soy protein. However, it seemed that the soy-based adhesive cross-linked by HPF with the maximum content of hydroxymethyl groups did not show the best water resistance.<\/jats:p>","DOI":"10.3390\/polym11020365","type":"journal-article","created":{"date-parts":[[2019,2,20]],"date-time":"2019-02-20T03:05:52Z","timestamp":1550631952000},"page":"365","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":44,"title":["Study on Soy-Based Adhesives Enhanced by Phenol Formaldehyde Cross-Linker"],"prefix":"10.3390","volume":"11","author":[{"given":"Zhigang","family":"Wu","sequence":"first","affiliation":[{"name":"Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming 650224, China"},{"name":"College of Forestry, Guizhou University, Guiyang 550025, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xuedong","family":"Xi","sequence":"additional","affiliation":[{"name":"Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming 650224, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6502-6493","authenticated-orcid":false,"given":"Hong","family":"Lei","sequence":"additional","affiliation":[{"name":"Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming 650224, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jiankun","family":"Liang","sequence":"additional","affiliation":[{"name":"Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming 650224, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jingjing","family":"Liao","sequence":"additional","affiliation":[{"name":"Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming 650224, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Guanben","family":"Du","sequence":"additional","affiliation":[{"name":"Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming 650224, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,2,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/j.ijadhadh.2014.01.026","article-title":"Cross-linked soy-based wood adhesives for plywood","volume":"50","author":"Lei","year":"2014","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Guo, M., and Wang, G. (2016). Milk Protein Polymer and Its Application in Environmentally Safe Adhesives. Polymers, 8.","DOI":"10.3390\/polym8090324"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3676","DOI":"10.1002\/app.36700","article-title":"Soybean meal-based adhesive enhanced by MUF resin","volume":"125","author":"Gao","year":"2012","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1163\/016942410X524147","article-title":"A soy flour-based adhesive reinforced by low addition of MUF resin","volume":"25","author":"Fan","year":"2011","journal-title":"J. Adhes. Sci. Technol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"754","DOI":"10.1016\/j.ijadhadh.2011.07.003","article-title":"A new formaldehyde-free wood adhesive from renewable materials","volume":"31","author":"Jang","year":"2011","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5380","DOI":"10.15376\/biores.8.4.5380-5391","article-title":"Preparation of wood adhesives based on soybean meal modified with PEGDA as a crosslinker and viscosity reducer","volume":"8","author":"Gao","year":"2013","journal-title":"Bioresources"},{"key":"ref_7","first-page":"70","article-title":"Effects of glyoxal on chemical structure and properties of protein-based adhesives","volume":"31","author":"Lei","year":"2011","journal-title":"J. Southwest For. Univ. China"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Lei, H., Wu, Z., Cao, M., and Du, G. (2016). Study on the soy protein-based wood adhesive modified by hydroxymethyl phenol. Polymers, 8.","DOI":"10.3390\/polym8070256"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1007\/s11746-006-1198-7","article-title":"Bond quality of soy-based phenolic adhesives in southern pine plywood","volume":"83","author":"Yang","year":"2006","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_10","unstructured":"Hse, C.Y., Fu, F., and Bryant, B.S. (2001). Development of formaldehyde-based wood adhesives with co-reacted phenol\/soybean flour. Green Chemistry for Adhesives, Proceedings of the Wood Adhesives 2000, South Lake Tahoe, CA, USA, 22\u201323 June 2000, Forest products Society."},{"key":"ref_11","unstructured":"Kreibich, R.E., Steynberg, P.J., and Hemingway, R.W. (1998, January 4\u20135). End jointing green lumber with SoyBond. Proceedings of the Wood Residues into Revenue, Residual Wood Conference, Richmond, BC, Canada."},{"key":"ref_12","first-page":"1","article-title":"Disruption of soy-based adhesive treated by Ca(OH)2 and NaOH","volume":"3","author":"Wu","year":"2013","journal-title":"J. Adhes. Sci. Technol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"4983","DOI":"10.1021\/jf0105081","article-title":"Tyrosine Cross-Links: Molecular Basis of Gluten Structure and Function","volume":"49","author":"Riblett","year":"2001","journal-title":"J. Agric. Food Chem."},{"key":"ref_14","first-page":"8","article-title":"Application of soy protein-based adhesives modified by cross-linker","volume":"27","author":"Lei","year":"2013","journal-title":"China Wood Ind."},{"key":"ref_15","first-page":"63","article-title":"Structural Progressing of Phenol-urea-formaldehyde Resin under Alkaline Condition","volume":"29","author":"Lei","year":"2009","journal-title":"China Chem. Ind. For. Prod."},{"key":"ref_16","first-page":"31","article-title":"Preparation of eco-friendly urea-formaldehyde resin by urea-formaldehyde precondensate and soy protein","volume":"1","author":"Wu","year":"2016","journal-title":"Chin. J. For. Eng."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1007\/s00226-015-0711-2","article-title":"Competitive Formation of the Methylene and Methylene ether Bridges in the Urea-formaldehyde Reaction in Alkaline Solution: A Combined Experimental and Theoretical Study","volume":"49","author":"Li","year":"2015","journal-title":"Wood Sci. Technol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1016\/j.indcrop.2015.05.066","article-title":"Soybean meal-based wood adhesive enhanced by ethylene glycol diglycidyl ether and diethylenetriamine","volume":"74","author":"Li","year":"2015","journal-title":"Ind. Crops Prod."},{"key":"ref_19","first-page":"8","article-title":"Research status on the utilization of forest and agricultural biomass in inorganic wood-based panel","volume":"1","author":"Wu","year":"2016","journal-title":"Chin. J. For. Eng."},{"key":"ref_20","unstructured":"Zuo, R. (2007). Preparation and Characterization of L-Alanyl-L-Glutamine-Zn2+ Chelate. [Master\u2019s Thesis, Chongqing University of China]."},{"key":"ref_21","unstructured":"Zhang, X. (2013). Multi-aldehydes Modified Environmentally Friendly Phenolic Resin Adhesive. [Master\u2019s Thesis, Beijing University of Chemical Technology]."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"955","DOI":"10.1016\/0032-3861(96)87277-6","article-title":"Phenolic resins: 4 Self-condensation of methylolpheols in formaldehyde-free media","volume":"37","author":"Larroque","year":"1996","journal-title":"Polymer"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1016\/j.progpolymsci.2004.01.004","article-title":"Advances in addition-cure phenolic resins","volume":"29","author":"Nair","year":"2004","journal-title":"Prog. Polym. Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"608","DOI":"10.1021\/ma00169a024","article-title":"Solid-state NMR study of the hexamethylenetetramine curing of phenolic resins","volume":"20","author":"Hatfield","year":"1987","journal-title":"Macromolecules"}],"container-title":["Polymers"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4360\/11\/2\/365\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:33:18Z","timestamp":1760185998000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4360\/11\/2\/365"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,2,19]]},"references-count":24,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2019,2]]}},"alternative-id":["polym11020365"],"URL":"https:\/\/doi.org\/10.3390\/polym11020365","relation":{},"ISSN":["2073-4360"],"issn-type":[{"value":"2073-4360","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,2,19]]}}}