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    Author(s): Daniel J. YelleJoseph E. Jakes; John Ralph; Charles R. Frihart
    Date: 2010
    Source: Wood Adhesives 2009 [electronic resource]. Madison, WI : Forest Products Society, c2010. [1 CD-ROM] : p. 338-342. ISBN: 9781892529572: 1892529572. FPS proceedings ; no. 7216-09.
    Publication Series: Miscellaneous Publication
    PDF: View PDF  (192.0 KB)

    Description

    Solution-state nuclear magnetic resonance spectroscopy (NMR) is a powerful tool for unambiguously determining the existence or absence of covalent bonds between wood components and adhesives. Finely ground wood cell-wall material dissolves in a solvent system containing dimethylsulfoxide-d6 and N-methyl–imidazole-d6, keeping wood component polymers intact and in a near-native state. Two-dimensional (2D) NMR experiments, using 13C-1H one-bond heteronuclear single-quantum coherence on non-derivatized cell-wall material from loblolly pine, reveal details about the major cell-wall polymer structures. This technique can detect new covalent bond formation between cell-wall polymers and wood adhesives. A monofunctional model of polymeric methylene diphenyl diisocyanate (pMDI) and also neat pMDI were reacted without catalysts with loblolly pine matchsticks under moisture-controlled conditions to chemically modify the wood cell-wall polymers. The modified matchsticks were ball-milled, dissolved, and characterized via 2D NMR experiments. Results showed that high concentrations of the pMDI model reacted to form carbamate linkages with mannan and lignin sidechain units at 160°C. However, the pMDI reacted matchsticks showed no reactivity at 160°C, thus indicating that the mechanism of durable bond formation between wood and pMDI is not controlled by urethane formation.

    Publication Notes

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    Citation

    Yelle, Daniel J.; Jakes, Joseph E.; Ralph, John; Frihart, Charles R. 2010. Characterizing polymeric methylene diphenyl diisocyanate reactions with wood. 1, High-resolution solution-state NMR spectroscopy. In: Wood Adhesives 2009 [electronic resource]. Madison, WI : Forest Products Society, c2010. [1 CD-ROM]: p. 338-342. ISBN: 9781892529572: 1892529572. FPS proceedings ; no. 7216-09.

    Keywords

    Adhesives, testing, glue, adhesion, nuclear magnetic resonance spectroscopy, plant cell walls, loblolly pine, dimethylsulfoxide, catalysis, chemical reactions, lignin, carbamates, isocyanates, hydroxyl group, gluing, wood bonding, bonding, methylene diphenyl diisocyanate, polymers, polymerization, loblolly pine, N-methyl-imidazole, durability, chemical modification of wood, mannan, phenyl isocyanate, PI

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https://www.fs.usda.gov/treesearch/pubs/56509