The chemical, kinetic and mechanical characterization of tannin-based adhesives with different crosslinking systems

International Journal of Adhesion and Adhesives

Volumn 68, Issue , 2016, Pages 1-8

  Böhm, Ricarda ^a   Hauptmann, Markus ^a   Pizzi, Antonio ^b,c   Friedrich, Christian ^a   Laborie, Marie Pierre ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSITÉ DE LORRAINE   (France)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Adhesive for wood; Cure hardening; Mechanical properties of adhesives; Tannin resins; Wood and wood composites

Indexed keywords

ADHESIVES; ALDEHYDES; CHEMICAL BONDS; CONDENSATION REACTIONS; CROSSLINKING; CURING; ELASTIC MODULI; FLAVONOIDS; KINETICS; MOLECULAR WEIGHT DISTRIBUTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS; TANNINS; WOOD;

CURE/HARDENING; MECHANICAL CHARACTERIZATIONS; MECHANICAL PROPERTIES OF ADHESIVES; MICROSCOPIC OBSERVATIONS; STRUCTURE PROPERTY RELATIONSHIPS; TANNIN RESINS; TANNIN-BASED ADHESIVES; WOOD COMPOSITES;

RESINS;

ADHESIVES; CHEMICAL REACTIONS; SYNTHESIS; SYNTHETIC POLYMERS; TANNINS;

EID: 84957811093     PISSN: 01437496     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijadhadh.2016.01.006     Document Type: Article

References (60)

1. Dunky M, Niemz P. Holzwerkstoffe und Leime; 2002
2. A. Pizzi, and H. Scharfetter The chemistry and development of tannin based adhesives for exterior plywood J Appl Polymr Sci 22 1978 1745 1761
3. A. Pizzi Tannin-based adhesives J Macromol Sci Rev Macromol Chem 18 1980 247 315
4. A. Pizzi Pine tannin adhesives for particleboard Holz als Roh-und Werkstoff 40 1982 293 301
5. P.C. Muller, S.S. Kelley, and W.G. Glasser Engineering plastics from lignin. IX. Phenolic resin synthesis and characterization J Adhes 17 1984 185 206
6. B. Dix, and R. Marutzky Tanninformaldehydharze als Bindemittel fuer Holzwerkstoffe WKI-Bericht 1987
7. A. Pizzi Advanced wood adhesives technology 1994 CRC Press
8. D.T. Rossouw, A. Pizzi, and G. McGillivray The kinetics of condensation of phenolic polyflavonoid tannins with aldehydes J Polym Sci: Polym Chem Ed 18 1980 3323 3343
9. N. Meikleham, and A. Pizzi Acid-and alkali-catalyzed tannin-based rigid foams J Appl Polym Sci 53 1994 1547 1556
10. D. Garcia, W. Glasser, A. Pizzi, C. Lacoste, and M.-P. Laborie Polyphenolic resins prepared with maritime pine bark tannin and bulky-aldehydes Ind Crops Prod 62 2014 84 93
11. L. Baekeland The synthesis, constitution, and uses of bakelite Ind Eng Chem 1 1909 149 161
12. A. Baeyer Ueber die Verbindungen der Aldehyde mit den Phenolen und aromatischen Kohlenwasserstoffen Berichte der deutschen chemischen gesellschaft 5 1872 1094 1100
13. V. Sealy-Fisher, and A. Pizzi Increased pine tannins extraction and wood adhesives development by phlobaphenes minimization Holz als Roh-und Werkstoff 50 1992 212 220
14. H. Coppens, M. Santana, and F. Pastore Tannin formaldehyde adhesive for exterior-grade plywood and particleboard manufacture For Prod J 30 1980 38 42
15. A. Pizzi, Dd.T. Rossouw, W. Knuffel, and M. Singmin Honeymoon'phenolic and tannin-based fast-setting adhesive systems for exterior grade finger joints Holzforschung und Holzverwertung 32 1980 140 150
16. A. Pizzi, E. Orovan, and F. Cameron Cold-set tannin-resorcinol-formaldehyde adhesives of lower resorcinol content Holz als Roh-und Werkstoff 46 1988 67 71
17. N. Meikleham, A. Pizzi, and A. Stephanou Induced accelerated autocondensation of polyflavonoid tannins for phenolic polycondensates. I. 13C NMR, 29Si NMR, Xray, and polarimetry studies and mechanism J Appl Polym Sci 54 1994 1827 1845
18. A. Pizzi, and A. Stephanou A 13C NMR study of polyflavonoid tannin adhesive intermediates. I. Noncolloidal performance determining rearrangements J Appl Polym Sci 51 1994 2109 2124
19. A. Pizzi, and A. Stephanou A 13C NMR study of polyflavonoid tannin adhesive intermediates. II. Colloidal state reactions J Appl Polym Sci 51 1994 2125 2130
20. R. Garcia, and A. Pizzi Polycondensation and autocondensation networks in polyflavonoid tannins. I. Final networks J Appl Polym Sci 70 1998 1083 1091
21. R. Garcia, and A. Pizzi Polycondensation and autocondensation networks in polyflavonoid tannins. II. Polycondensation versus autocondensation J Appl Polym Sci 70 1998 1093 1109
22. Roll W A P, Dombo B. Bindemittellösungen für Cellulosehältige Produkte, Germany, 1994; C1; 2001
23. W. Roll A.P., P.Stracke Bindemittelzusammensetzung, ihre Verwendung sowie ein Verfahren zur Herstellung von Spanplatten US, EP 1998
24. W. Roll A.P., Dombo B., Bindemittelgemisch, German Patent 1993, C2; 1999.
25. C. Lacoste, M. Basso, A. Pizzi, M.-P. Laborie, D. Garcia, and A. Celzard Bioresourced pine tannin/furanic foams with glyoxal and glutaraldehyde Ind Crops Prod 45 2013 401 405
26. A. Ballerini, Al Despres, and A. Pizzi Non-toxic, zero emission tannin-glyoxal adhesives for wood panels Holz als Roh-und Werkstoff 63 2005 477 478
27. A. Pizzi Wood adhesives chemistry and technology Marcel Dekker 1983 Marcel Dekker
28. P. Navarrete, A. Pizzi, H. Pasch, K. Rode, and L. Delmotte MALDI-TOF and 13 C NMR characterization of maritime pine industrial tannin extract Ind Crops Prod 32 2013 105 110
29. E. Cadahia, E. Conde, M. Garcia-Vallejo, and B.Fn de Simón Gel permeation chromatographic study of the molecular weight distribution of tannins in the wood, bark and leaves of Eucalyptus spp Chromatographia 42 1996 95 100
30. J. Wang, M.-P.G. Laborie, and M.P. Wolcott Kinetic analysis of phenol formaldehyde bonded wood joints with dynamical mechanical analysis Thermochim Acta 491 2009 58 62
31. J. Grüner Mykologische und histologischeUntersuchungen zur Grobborkigkeitbei geschädigten Rotbuchen (Fagus sylvaticaL.), Fakultät für Forst- und Umweltwissenschaften 2009 Albert-Ludwigs-Universität Freiburg 140
32. H. Lei, A. Pizzi, G. Du, and A. Despres Variation of MUF and PMUF resins mass fractions during preparation J Appl Polym Sci 100 2006 4842 4855
33. R.W. Hemingway, and G.W. McGraw Formaldehyde condensation products of model phenols for conifer bark tannins J Liquid Chromatogr 1 1978 163 179
34. M. Fechtal, B. Riedl, and L. Calve Modeling of tannins as adhesives. I. Condensation of the (+)-catechin with formaldehyde Holzforschung-Int J Biol, Chem Phys Technol Wood 47 1993 419 424
35. C. Zhao, A. Pizzi, and S. Garnier Fast advancement and hardening acceleration of low condensation alkaline PF resins by esters and copolymerized urea J Appl Polym Sci 74 1999 359 378
36. A. Pizzi, X. Lu, and R. Garcia Lignocellulosic substrates influence on TTT and CHT curing diagrams of polycondensation resins J Appl Polym Sci 71 1999 915 925
37. Cd Saucier, G. Bourgeois, C. Vitry, D. Roux, and Y. Glories Characterization of (+)-catechin-acetaldehyde polymers: a model for colloidal state of wine polyphenols J Agric Food Chem 45 1997 1045 1049
38. X. Lu, and A. Pizzi Curing conditions effects on the characteristics of thermosetting adhesives-bonded wood joints Part 1: Substrate influence on TTT and CHT curing diagrams of wood adhesives Holz als Roh-und Werkstoff 56 1998 339 346
39. G. He, and N. Yan Effect of wood species and molecular weight of phenolic resins on curing behavior and bonding development Holzforschung 59 2005 635 640
40. J. Lopez, C. Ramirez, A. Torres, M. Abad, L. Barral, J. Cano, and et al. Isothermal curing by dynamic mechanical analysis of three epoxy resin systems: gelation and vitrification Journal of applied polymer science 83 2002 78 85
41. L. Onic, V. Bucur, M.P. Ansell, A. Pizzi, X. Deglise, and A. Merlin Dynamic thermomechanical analysis as a control technique for thermoset bonding of wood joints Int J Adhes Adhes 18 1998 89 94
42. G. He, and N. Yan Influence of the synthesis conditions on the curing behavior of phenol urea formaldehyde resol resins J Appl Polym Sci 95 2005 1368 1375
43. R. Follensbee, J. Koutsky, A. Christiansen, G. Myers, and R. Geimer Development of dynamic mechanical methods to characterize the cure state of phenolic resole resins J Appl Polym Sci 47 1993 1481 1496
44. J. Wang, M.-P.G. Laborie, and M.P. Wolcott Application of beam mechanics to sensing the cure development of wood-phenolic joints by dynamic mechanical analysis Thermochim Acta 465 2007 18 24
45. S. Garnier, and A. Pizzi CHT and TTT curing diagrams of polyflavonoid tannin resins J Appl Polym Sci 81 2001 3220 3230
46. S. Kim, and H.-J. Kim Curing behavior and viscoelastic properties of pine and wattle tannin-based adhesives studied by dynamic mechanical thermal analysis and FT-IR-ATR spectroscopy J Adhes Sci Technol 17 2003 1369 1383
47. F.A. Kamke, and J.N. Lee Adhesive penetration in wood a review Wood Fiber Sci 39 2007 205 220
48. S.E. Johnson, and F.A. Kamke Quantitative analysis of gross adhesive penetration in wood using fluorescence microscopy J Adhes 40 1992 47 61
49. A. Singh, B. Dawson, C. Rickard, J. Bond, and A. Singh Light, confocal and scanning electron microscopy of wood-adhesive interface Microsc Anal-UK 2008 5
50. A. Pizzi, and A. Stephanou A comparative C13 NMR study of polyflavonoid tannin extracts for phenolic polycondensates J Appl Polym Sci 50 1993 2105 2113
51. A.L. Davis, Y. Cai, A.P. Davies, and J. Lewis 1H and 13C NMR assignments of some green tea polyphenols Magn Reson Chem 34 1996 887 890
52. A. Pizzi, and N. Meikleham Induced accelerated autocondensation of polyflavonoid tannins for phenolic polycondensates. III. CP MAS 13C NMR of different tannins and models J Appl Polym Sci 55 1995 1265 1269
53. A. Pizzi, and P. Tekely Mechanism of polyphenolic tannin resin hardening by hexamethylenetetramine: CPMAS 13C NMR J Appl Polym Sci 56 1995 1645 1650
54. G. Tondi, and A. Pizzi Tannin-based rigid foams: characterization and modification Ind Crops and Prod 29 2009 356 363
55. S. Ohara, and R.W. Hemingway Condensed tannins: the formation of a diarylpropanol-catechinic acid dimer from base-catalyzed reactions of (+)-catechin J Wood Chem Technol 11 1991 195 208
56. P. Navarrete, A. Pizzi, F. Bertaud, and S. Rigolet Condensed tannin reactivity inhibition by internal rearrangements: detection by CP-MAS 13C NMR, Maderas Ciencia y tecnologia 13 2011 59 68
57. P. Kiatgrajai, J. Wellons, L. Gollob, and J.D. White Kinetics of epimerization of (+)-catechin and its rearrangement to catechinic acid J Org Chem 47 1982 2910 2912
58. K. Hashida, and S. Ohara Formation of a novel catechinic acid stereoisomer from base-catalyzed reactions of (+)-catechin J Wood Chem Technol 22 2002 11 23
59. P. Mehta, and W. Whalley 1016. The stereochemistry of some catechin derivatives J Chem Soc 1963 5327 5332
60. A. Pizzi, N. Meikleham, and A. Stephanou Induced accelerated autocondensation of polyflavonoid tannins for phenolic polycondensates. II. Cellulose effect and application J Appl Polym Sci 55 1995 929 933