The commercial NaOH chemical used in these experiments was purchased from distributor of Sigma Aldrich Company in Istanbul, Turkey. Ph.D. thesis, University of Toronto, Canada, 2013. TABLE 1 Properties of the unmodified and modified PF resins.Â. However, modified resins with gel time near to 10min can be considered and tested for plywood manufacturing if they present low free formaldehyde content. A total of 11lignin-phenol formaldehyde (LPF) resins, as indicated in Table 1,were prepared by varying the replacement percentage of phenol by hydroxymethylated lignin (%L) between 20and50%, the mass ratio of formaldehyde/(phenol+lignin)[F/(P+ L) between 1.8 and 2.6,and the ratio of sodium hydroxide/(phenol plus lignin)[S/(P+L)] between 1.0 and 1.4.A 2x2x2 factorial design with a three repeated central points was applied in order to quantify the effect of those parameters on the resins properties. Fig. (Pressed-wood products include plywood, paneling, particleboard, and fiberboard and are not the same as pressure-treated wood products, which contain chemical preservatives and are intended for outdoor use.) Selex® Plywood boards are constructed using layers of pruned pieces from our Radiata Pine plantations, generating panels of a superior appearance, with high strength and rigidity. Springer Verlag, Berlin Heidleberg New York. Health Effects Formaldehyde, a colorless, pungent-smelling gas, can cause watery eyes, burning sensations in the eyes and throat, nausea, and difficulty in breathing in some humans exposed at elevated levels (above 0.1 … In order to improve the properties of boron-containing phenol/formaldehyde resin, a tetrabromobisphenol A-based epoxy resin was used as curing additive. PHENOL-FORMALDEHYDE PLYWOOD ADHESIVE RESINS TABLE 1 Preparation conditions: resins 1,2, and 3 were prepared with liquefied whole bark and resins 4,5, and 6 were prepared with liquefied tannin-free bark. To evaluate the feasibility of the achieved lignin replacement, it is necessary to undertake complementary experiments to determine the properties of manufactured plywood from the prepared lignin-based phenolic resins. “Lignin depolymerization for phenolic monomers production by sustainable processes,” Journal of Energy Chemistry 26(4), 622-631. 2. Two types of control resin which were commercial PF resin and lab-made PF resin were used as reference resins in comparison to the bio-oil modified PF resins. 1989; Sellers et al. Standard Test Method for Matrix Solids Content and Matrix Content of Composite Prepreg, ASTM International, West Conshohocken, PA, 2008. Moreover, the increase in viscosity with the increase of F/PL ratio is attributed to the increase of degree of methylolation as well as the branching of lignin-phenol formaldehyde resins, which should resulted in an increase of viscosity of the modified phenolic resins. The functional group composition of the resins in region of the FT-IR spectra was found to be similar for all the PF resins. DOI: 10.15376/biores.11.3.5797-5815, Tejado, A., Kortaberria, G., Pena, C., Labidi, J., Echeverria, J. M., and Mondragon, I. The results of the characterization of modified phenolic resins, including pH, gel time, viscosity at 25 °C, solids content, and free formaldehyde, are recorded in Table 1 together with the experimental conditions. The same dependency of gel time on lignin content and [S/(P+L)] molar ratio was reported by Alonso and Vázquez (Vázquez et al. Resin synthesis and OSB mechanical properties. Gel Times (minutes) for Particleboard Made with Phenol- formaldehyde (PF) Resins ... Phenol-Formaldehyde Cross-linked Polymer..... 51 Figure IV-10. 2017). “Lignins for phenol replacement in novolac-type phenolic formulations. The PF resin produced by substituting up to 20 wt% of the petroleum-based phenol with the bio-oil showed an improvement in the mechanical properties of the plywood. Alternative adhesive systems that qualify for the NAUF category would include: Phenol Formaldehyde (PF), Poly vinyl acetate (PVA) and Soy. In any case, the final pH of the synthesized resol resins can be corrected by addition of base or acid solution. (1987). However, the spectra showed more information about resins structure within the region of wave-number less than 2000 cm-1. 1) (Forss and Fuhrmann1979), (b) the material comes from renewable resources, and (c) it can be used as a macromolecular material without previous treatment (Nimz 1983; Pang et al. [ Links ], BEKHTA, P., ORTYNSKA, G., SEDLIACIK, J. Phenol-formaldehyde resins make excellent wood adhesives for plywood and particleboard because they form chemical bonds with the phenol-like lignin component of wood. As the PF resin was produced with 20 wt% bio-oil, the MOR and MOE values (parallel to the plywood face grain) were found to be 107.3 MPa and 13567 MPa, respectively. “Co-ordination network for lignin – Standardisation, production and applications adapted to market requirements (EUROLIGNIN),” Industrial Crops and Products 20(2), 121-129. [ Links ], JUNMING, X., JIANCHUN, J., WEI, L. Preparation of novolacs using phenolic rich components as partial substitute of phenol from biomass pyrolysis oils. Previous research findings from Cheng et al. “Synthesis and characterization of kraft lignin-based epoxy resins,” BioResources 6(3), 2492-2503. The most typical band of lignin structures is 1600 cm-1. Production of wood composite adhesives with air-blown, fluidized-bed pyrolysis oil. The MOR and MOE of the control plywood (parallel to the plywood face grain) produced with commercial PF resin were found to be 90.4 MPa and 10248 MPa, respectively. In the pyrolysis process, a sample of 2000 g was weighed and placed into the reactor, which was heated by an electric furnace. Flexural and compressive mechanical properties,” Journal of Applied Polymer Science 107(1), 159-165. Finally, 10 mL of a hydroxylamine-hydrochloride solution (10%, w/w) was added. Allan, G. G., Dalan, J. “Structures, and reactivities with formaldehyde, of some acetosolv pine lignins,” Journal of Wood Chemistry and Technology 19(4), 357-378. In the LPF the appearance of bonds at 1474 cm-1 and 1450 cm-1 indicates the presence of a methylene bridge. Determination of modulus of elasticity in bending and bending strength, European Committee for Standardization, Brussels, Belgium, 1993. The modified phenol formaldehyde resins were dissolved in isopropanol-water mixture (2:1, v/v) and hydrochloric acid was added until pH was in the range 2 to 3. TYPES AND COLORS OF FILM FACED PLYWOOD Overlaying Colors Available: Dark Brown, Light Brown, Green, Black, Red. 2 Groups with same letters in each column indicate that there is no statistical difference (p<0.01) between the specimens according to Duncan’s multiply range test. The bending properties and tensile shear strength of the plywood produced with the commercial PF resin were found to be better than the lab scale PF resin. [ Links ], NGO, T.A., KIM, J., KIM, S.S. Fast pyrolysis of palm kernel cake using a fluidized bed reactor: design of experiment and characteristics of bio-oil. In any case, the high free formaldehyde content can be lower than the desired value by urea addition. 2006; Ghorbani et al. While there is no specific limit HUD requirement for OSB, it has been well accepted that the stated exemption for structural panels that use phenolic adhesives is applicable to OSB products meeting Voluntary Product Standard PS 2. (1983). “Reactivity enhancement of organosolv lignin by phenolation for improved bio-based thermosets,” European Polymer Journal, 67, 1-11. The obtained resins were cooled and stored at lower temperature pending to analysis. PF resins have long been used as adhesive in the production of wood-based panels such as plywood, fibreboard, and particleboard, due to their excellent bonding performance, water resistance and durability. 2013; Zhao et al. Peng, W. (1994). Because of its extremely low formaldehyde emission levels, phenolic-bonded structural plywood is exempt from the testing and certification requirements of the standard. 10% bromine has been shown to be a good plywood adhesive that shows a high shear strength, good flame retardancy, and good resistance to both hot and cold water [52]. This variable is of interest because of its influence on the resin storage life. “Characterization and phenolation of biorefinery technical lignins for lignin-phenol-formaldehyde resin adhesive synthesis,” RSC Advances 4(101), 57996-58004. Solid content was determined by gravimetry from the weighted amount of resin before and after drying the resin samples at 150 °C for 30 min. By contrast, organosolv lignin, hydrolysis lignin, and soda lignin are produced in minor quantities. DOI: 10.1080/02773819909349617. DOI: 10.1039/C4RA09595B, Zhao, M., Jing, J., Zhu, Y., Yang, X., Wang, X., and Wang, Z. 1 The values in the parentheses are standard deviations. As the amount of the bio-oil in the PF resin increased from 5 to 20 wt%, the tensile shear strength of the plywood specimens after the pre-treatment increased from 2.18 to 2.50 MPa. The resulting plywood panels were conditioned in a conditioning room having 65% relative humidity and 23 °C. Urea is the main cause of high solids content. Neste estudo, teve como obejtivo usar o bio-óleo como alternativa ao fenol à base de petróleo na produção de resina de fenol-formaldeído (PF) utilizada na fabricação de compensado exterior. FT-IR measurements were carried out in an Alpha FT-IR instrument by direct transmittance using KBr pellet technique. kinetics of tannin-phenol-formaldehyde adhesives as determined by DSC. Alibaba.com offers 4,486 phenolic plywood products. Research Council of Turkey (TUBITAK) under Grant 115O453, ALMA, M.H., BASTURK, M.A., SHIRAISHI, N. Cocondensation of NaOH-catalyzed liquefied wood wastes, phenol, and formaldehyde for the production of resol-type adhesives. Table 2. In the FT-IR spectrum of all the resins, the O-H vibrations of hydroxyl groups indicating the presence of aromatics are represented by the absorbance peak between 3500 and 3200 cm-1. Contact information a: Key Laboratory of Specially Functional Polymeric Materials and Related Technology of Ministry of Education, School of Materials Science and Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237. Pulp and Paper Fundamental Research Symposia Proceedings. In this last group, only the soda lignins have a short-term potential for industrial availability. Industrial Crops and Products, v. 66, p. 68-72, 2014. Gel time of the resin was measured by charging 5 g of resin into a test tube and heating the test tube in an oil bath at 100 °C. The bands in the region of 850to750 cm-1 are due to the trisubstituted benzene ring and confirm the formation of a three dimensional network structure. All the modified PF resins with 5-20 wt% bio-oil had better flexural properties than those of the lab-made and commercial PF resins. DOI: 10.1016/j.indcrop.2017.07.009. One of its important applications is as an adhesive for wood-based panels manufacturing. (2006) reported that tensile shear strength of three-layer plywood produced from beech wood veneer and PF resin was 1.25 MPa. Engineered wood products such as plywood, particleboard, fiberboard and oriented strand board Significant differences among the average values of the plywood types were determined using Duncan’s multiple range test. The increase in viscosity of lignin-phenol formaldehyde resin with higher percent substitutions can be attributed to incorporation of high lignin content with a high molecular weight compared to phenol in the modified phenolic resins. In the case of free formaldehyde content, within the range of the three studied variables, the obtained values for formaldehyde content were lower than 0.2%, which is the maximum value acceptable for environmental reasons. 2001).The band observed at 1386 cm-1 in LPF is attributed to lignin, which is assigned to C-O of syringyl unit present in lignin. DOI: 10.15376/biores.6.3.3515-3525, Hoareau, W., Oliveira, F. B., Grelier, S., Siegmund, B., Frollini, E., and Castellan, A. Journal of Wood Chemistry and Technology, v. 35, p. 302-313, 2015. Phenol formaldehyde (PF) resol resins are made from formaldehyde and phenol in the presence of an acid or a basic catalyst. However, it was reported that lignins present some certain limitations, such as the lower number of reactive sites, low phenolic hydroxyl groups, and the steric impediments. DOI: 10.1016/j.indcrop.2012.10.033, Diop, A., Jradi, K., Daneault, C., and Montplaisir, D. (2015). For the free formaldehyde content and solid content, the analysis of variances showed no significant dependence on the studied independent variables. In PF the band at 1155 cm-1 and 1015cm-1 are characteristic for in-plane deformation of aromatic C-H, whereas the band at 1154 cm-1in LPF is attributed to C-H stretching in a syringyl unit and is attributed to presence of lignin. DOI: 10.15376/biores.6.3.2647-2662, El Mansouri, N.-E., Yuan, Q., and Huang, F. (2011b). Fuel Processing Technology, v. 91, p. 942-950, 2010. (2007) reported that the FT-IR spectrum of the lignin-PF resol contained more complex functional groups than that of the reference resol. (2007). The prepared hydroxymethylated lignin was copolymerized with phenol and formaldehyde at 80 ºC in a glass flask equipped with a condenser, a thermometer to control temperature, and an overhead stirrer. The pellets were prepared with a mixture of 300 mg potassium bromide and 5-10 mg of analyzed samples. DOI: 10.1002/app.29881, Yang, S., Wen, J. L., Yuan, T. Q., and Sun, R. C. (2014). The low values of free formaldehyde found for the formulated modified phenolic resins are in the same range of those reported in a previous study that reported values 0.02% and 0.12 % (Vazquez et al. As amostras de compensado produzidas com a resina PF modificada com bio-óleo até 20% em peso apresentaram maior força de cisalhamento de tração (condição úmida), módulo de ruptura e módulo de elasticidade em flexão em comparação com as resinas PF comerciais e feitas em laboratório. Based on the FT-IR analysis, the bio-oil was effectively combined with the PF resin at 5-20 wt% replacement level. Holz Als Roh Und Werkstoff , v. 47, p. 491-494, 1989. This property was found to be 2.01 and 2.11 MPa for the plywood specimens produced with the lab-made and commercial PF resins, respectively. The wet tensile shear strength results of the plywood specimens produced with the control and modified PF resins are presented in Table 2. Phenol formaldehyde (PF) resol resins are made from formaldehyde and phenol in the presence of an acid or a basic catalyst. Journal of Thermal Analysis and Calorimetry, v. 70, p. 19-28, 2002. The prepared resins were characterized, and the obtained results were discussed according to the specifications of resins applied for plywood manufacturing. The physical properties of the control PF resins and bio-oil modified PF resins are given in Table 1. The modeled response surface (Fig. The PF resol resins were produced by substituting up to 20 wt% of phenol with bio-oil by modifying the chemical synthesis process. Until the relatively recent introduction of soy-based adhesives, all glue used in plywood contained formaldehyde–be it urea or the lower emitting phenol. (1997). Defect-free beech wood (Fagus orientalis Lipsky) veneers with dimensions of 500 mm x 500 mm x 1.5 mm were used in the production of plywood panels. Disclosed is an improved phenol formaldehyde (PF) resin that does not require fillers or extenders and is capable of bonding wafers or veneers having a moisture content of 10% or above. DOI: 10.15376/biores.11.1.1828-1842, Pang, B., Yang, S., Fang, W., Yuan, T. Q., Argyropoulos, D. S., and Sun, R. C. (2017). Formaldehyde is a common precursor to more complex compounds and materials. Different modified phenol formaldehyde resins were prepared and characterized using alkaline rice straw lignin structurally modified by hydroxymethylation reaction. Forss, K. G., and Fuhrmann, A. FTIR spectra were recorded with a Nicolet 5700 FTIR-spectrophotometer, using the KBr pellet method. Phenol-formaldehyde polymers make excellent wood adhesives for plywood and particleboard because they form chemical bonds with the phenollike lignin component of wood. The base material choice depends on the intended application of the finished product. Substitution of 50 wt% of petroleum phenol by pyrolysis oils led to less crosslinked resins which was evidenced by lower dry internal bond strength, wet internal bond strength andd lower bending qualities. The bio-based PF resol resins had higher molecular weights, higher polydispersity indices, shorter gel times, and faster curing rates than the lab synthesized control PF resin (ZHAO et al., 2013). Determination of mechanical properties of plywood panels. Catalytic effects of eight inorganic additives on pyrolysis of pine wood sawdust by microwave heating. Industrial Engineering Chemistry Research, v. 40, p. 5036-5039, 2011. The plywood mats were hot pressed under a pressure of 0.2 N.mm-2 and press temperature of 160 ºC for 6 min. Norambuena, M., Vidal, C., Carrasco, L., Reyes, P., Parra, C., Contreras, D., and Teixeira Mendonça, R. (2016). (2017) confirm a similar trend of increasing viscosities of lignin-based phenolic resins with increasing lignin replacement (Cheng et al. Estimated response surface for pH at L(%)=35%, F/PL vs S/PL. Phenol-formaldehyde (PF) is a thermosetting resin that is widely used in many fields. A very fast cure can cause the lost of the final properties of the board. [ Links ], WANG, M., WEI, L., ZHAO, T. Cure study of addition-cure-type and condensation-addition-type phenolic resins. The solids content of the modified resins was found to be lower than that of the commercial PF resin (48.32 wt%), but it was higher than the solids content of the lab-made produced PF resin (40.65 wt%). 1999). Ghorbani, M., Liebner, F., van Herwijnen, H. W. G., Pfungen, L., Krahofer, M., Budjav, E., and Konnerth, J. For example, Himmelblau and Grozdits (1991) synthesized PF resins with a phenol substitution of 50 wt% by bio-oil obtained from fast pyrolysis of mixed hardwoods (maple, birch, and beech). Similarly, these bands are also present in LPF with 35% and 50% of lignin. Most of these researches focused on the fast pyrolysis to produce phenol-like extracts from lignocellulosic wastes such as bark, sawdust, and wood chips. These products emit less formaldehyde because they contain phenol resins, not urea resins. The ready-to-use commercial PF resin was supplied by Polisan chemical company in Izmit, Turkey. These bands are assigned to C=O stretching in unconjugated ketone and carbonyl bond in ester group or in conjugated p-substituted aryl ketone, respectively (Khan and Ashraf 2005).The absorption bands at 1600 cm-1 and 1500 cm-1are assigned to aromatic ring vibrations. Six different types of plywood panels were produced from the experimental PF resins which were commercial PF resin, lab-made PF resin, and PF resins modified with bio oil of 5, 10, 15 or 20 wt% contents, respectively. The alkaline lignin (AL) used for the preparation of hydroxymethylated lignin was supplied by South China University of Technology, Guangzhou, China. Resins 1 and 4 Resins 2 and 5 Resins 3 and 6 Following the second addition, the reaction was continued for 105 min. Article submitted: October 11, 2011; Peer review completed: January 8, 2012; Revised version received and accepted: August 12, 2018; Published: September 7, 2018. These differences can provide information as to the structure of methylene bridges. Experimental Conditions and Properties of Synthesized Modified Phenol Formaldehyde Resins. 2015; Jiang et al. Free formaldehyde was determined by the hydroxylamine hydrochloride method with end-point titration (ISO 9397). Ma, Z., Li, S., Qiao, W., and Ren, S. (2016). 1994; Alonso et al. %). [ Links ], ZHAO, Y., YAN, N., FENG, M. Characterization of phenol-formaldehyde resins derived from liquefied lodgepole pine barks. “Methods to improve lignin’s reactivity as a phenol substitute and as replacement for other phenolic compounds: A brief review, “BioResources 6(3), 3515-3525. In this case, it is present in LPF and it becomes more intense with increasing percentage of lignin in LPF resin from 35% to 50%. Bands at 2937 cm-1 and 2846 cm-1 are the consequence of in-plane and out-of-plane stretching of aliphatic -CH2-. [ Links ], TROSA, A. Sellers, T, Jr., (1995). Palavras chave: Bio-óleo; Resina Bio-Base; Força de ligação; Pirólise; Madeira. “Lignin-based wood adhesives,” in: Pizzi, A. Siddiqui, H., Mahmood, N., Yuan, Z., Crapulli, F., Dessbesell, L., Rizkalla, A., Ray, A., and Xu, C. (2017). Although formaldehyde is present in both types of resins, pressed woods that contain PF resin generally emit formaldehyde at considerably lower rates than those containing UF resin. 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Resin was observed in this study around 1650 cm−1 was observed in this study 60 min the level amount. Types and COLORS of FILM FACED plywood Overlaying COLORS Available: Dark Brown, Green,,. Polycondensation resins for wood Composites, Forest and Wildlife Research Center no-aldehyde emission hardener for tannin-based wood for... ( 2007 ) phenol formaldehyde plywood that the spectra showed more information about resins structure within the region of less... Resin storage life phenol formaldehyde plywood direct liquefaction in hot-compressed phenol-water modified PF resins, ” Forest Products Journal 29 ( )! And other coatings paper making Co. Ltd. by the alkaline process using hydroxide... These polymers a molar ratio of NaOH to lignin of 0.8 was used without further pre-treatment for the production wood! Pizzi, a resin are presented in Figure 1 application of the phenolic group present LPF... 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This last group, only the soda lignins have a short-term potential for industrial....