In the early studies related to the use of lignin for phenolic resins manufacturing, different types of unmodified lignins, which were obtained directly from the pulping liquor, were investigated. “Lignin depolymerization for phenolic monomers production by sustainable processes,” Journal of Energy Chemistry 26(4), 622-631. However, a current trend is to use modified lignins in order to increase their reactivities towards formaldehyde (Alonso et al. “The isolation and characterization of lignin of kenaf fiber,” Journal of Applied Polymer Science 114(3), 1896-1901. Phenol and formaldehyde are charged into the kettle in specified quantaties. This resin has good chemical resistance, electrical insulation, and dimensional stability, but the price and environmental concerns may limit usage in some applications. Siddiqui, H., Mahmood, N., Yuan, Z., Crapulli, F., Dessbesell, L., Rizkalla, A., Ray, A., and Xu, C. (2017). Encyclopædia Britannica, Inc. 7. The same dependency of gel time on lignin content and [S/(P+L)] molar ratio was reported by Alonso and Vázquez (Vázquez et al. Chemical Reaction Phenol Formaldehyde resins are prepared by reaction of phenol with formaldehyde in the presence of acidic or basic catalyst. II. FTIR spectrum of lignin raw material. “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. Table 5.Analysis of Variance for Viscosity at 25 °C, Fig. (2017). DOI: 10.1002/app.2119, Alonso, M. V., Oliet, M., Rodriguez, F., Astarloa, G., and Echeverria, J. M. (2004). They were near to the range of values of the commercial resins used for plywood production, which ranges from 45to47% (Alonso et al. About I am having an experience and expertise over 30 years of Chemical process and plant Operations in the manufacturing of Melamine / Urea and Phenol Formaldehyde Resin uses in Particle Boards and all types of Wooden Boards with a very nice handling of Paper Impregnation Process. “Lignin-based wood adhesives,” in: Pizzi, A. Fig. The prepared resins were characterized according to gel time, solids content, viscosity, and free formaldehyde.The values for these parameters must be in agreement with commercial resins specifications applied for plywood. Structure of PF resin and lignin (Forss and Fuhrmann 1979). Fig. DOI:10.15376/biores.11.3.6867-6879. 1987; Allan et al. However the second type of catalyst achieves almost complete methanol conversion. In any case, the high free formaldehyde content can be lower than the desired value by urea addition. The alkaline lignin (AL) used for the preparation of hydroxymethylated lignin was supplied by South China University of Technology, Guangzhou, China. The initial reaction in all cases involves the formation of a hydroxymethyl phenol: The hydroxymethyl group is capable of reacting with either another free ortho or para site, or with another hydroxymethyl group. 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. “Kraft lignin behavior during reaction in an alkaline medium,” Biomass & Bioenergy 35(5), 2072-2079. For that, the unmodified lignins are relatively reluctant to undergo either self-condensation or condensation with formaldehyde, phenol, or phenol formaldehyde prepolymer (Vázquez et al.1999). “Characterization of alkaline lignins for use in phenol-formaldehyde and epoxy resins,” BioResources 6(3), 2647-2662. Norm ISO 9397. “Synthesis and characterization of kraft lignin-based epoxy resins,” BioResources 6(3), 2492-2503. 1999). “Hydrothermal degradation of enzymatic hydrolysis lignin in water-isopropyl alcohol co-solvent,” BioResources 11(3), 6867-6879. Treatment of phenol-formaldehyde resin manufacturing wastewater by the electrocoagulation process February 2012 Desalination and water treatment 39(1-3):176-181 2011; Jung et al. Being thermosets, hydroxymethyl phenols will crosslink on heating to around 120 °C to form methylene and methyl ether bridges through the elimination of water molecules. July 25, 1989 VA Specialty paper manufacturing; release of phenolic resin and methanol from process vessel. (1979). The gel time is an important parameter to take into consideration when resins are formulated, because it determines the resins reactivities. PF resins are manufactured in batch process. A polymeric compound obtained by polycondensation of a phenolic compound and an aldehyde compound under acidic or basic conditions generally refers to a resin synthesized from phenol and formaldehyde, and is called a phenol-formaldehyde resin (PF). 1). It is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commercial synthetic resins (plastics). R. S. Skinner, M. T. Skubiak, and D. H. Wetherell. “Some properties and chemical-structure of phenolic resins and their derivatives,” Journal of Applied Polymer Science 28(2), 531-542. Organosolv lignin and modified phenolic resin,” MokuzaiGakkaishi 40(10), 1073-1078. “Fourier transform infrared spectroscopy,” in: Methods in Lignin Chemistry, Li n, S.Y., and Dence, C. W. Phenol-formaldehyde (PF) is a thermosetting resin that is widely used in many fields. “Characterization and phenolation of biorefinery technical lignins for lignin-phenol-formaldehyde resin adhesive synthesis,” RSC Advances 4(101), 57996-58004. “Isolation and characterization of lignin from the oak wood bioethanol production residue for adhesives,” International Journal of Biological Macromolecules 72, 1056-1062. A molar ratio of NaOH to lignin of 0.8 was used, which resulted in a final pH of 12.3. Formation of phenol-formaldehyde resins. 2. The Manufacturing Process A. Phenol-formaldehyde is degraded by the white rot fungus Phanerochaete chrysosporium. Novolaks (or novolacs) are phenol-formaldehyde resins with a formaldehyde to phenol molar ratio of less than one. “Modification of ammonium lignosulfonate by phenolation for use in phenolic resins,” Bioresource Technology 96(9), 1013-1018.DOI: 10.1016/j.biortech.2004.09.009, Cheng, S., Yuan, Z., Leitch, M., Anderson, M., and Charles, C. (2013). (2017) confirm a similar trend of increasing viscosities of lignin-based phenolic resins with increasing lignin replacement (Cheng et al. 2006; Ghorbani et al. 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. A glass flask equipped with a condenser, a thermometer, and an overhead stirrer was charged with the above solution, and then formaldehyde aqueous solution was added according to the molar ratios of formaldehyde to lignin of1.0. and Duramold. A., and Foster, N. C. (1989). Our solid RESI-FLAKE ® resins were developed for use in the production of foundry shell molds and cores by the hot-sand process. These differences can provide information as to the structure of methylene bridges. Base-catalysed phenol-formaldehyde resins are made with a formaldehyde to phenol ratio of greater than one (usually around 1.5). 3) shows that for L=35%, the pH increased with increase of (S/PL) molar ratio. Finally, 10 mL of a hydroxylamine-hydrochloride solution (10%, w/w) was added. (2011).”Challenges in industrial applications of technical lignins,”BioResources 6(3), 3547-3568. The higher or lower values indicate a slow or fast curing reaction, respectively. The obtained mixture was heated to 50ºC and kept at this temperature for 8 h according to the optimum conditions reported in our previous research works on lignin hydroxymethylation (El Mansouri et al. ), Springer, Berlin., Heidelberg, 83-109. Sellers, T., Lora, J. H., and Okuma, M. (1994). Table 2 lists the results of fitting the data for pH (Y1), gel time (Y2) and viscosity (Y3) with polynomials of the form (Eq. DOI: 10.1002/app.29881, Yang, S., Wen, J. L., Yuan, T. Q., and Sun, R. C. (2014). (2016). Estimated response surface for gel time at [F/(P+L)]=2.2, L(%) vs.[S/(P+L)]. The diagram of the entire experimental protocol is shown in Fig.2. [1][2] There are many variations in both production and input materials that are used to produce a wide variety of resins for special purposes. (2006). Lignin–Adhesive Research for Wood Composites, Forest and Wildlife Research Center. The bands at 1120 cm-1 is characteristic of aromatic C-H in S units of lignin molecule and the C-O of primary alcohol at 1044 cm-1. However, the spectra showed more information about resins structure within the region of wave-number less than 2000 cm-1. The statistical analysis was carried out by using Statgraphics 18 Centurion. “Alkali lignin depolymerization under eco-friendly and cost-effective NaOH/urea aqueous solution for fast curing bio-based phenolic resin,” Industrial Crops and Products 120, 25-33. Allan, G. G., Dalan, J. Table 2. (1992). “Lignocellulosic ethanol residue-based lignin-phenol-formaldehyde resin adhesive,” International Journal of Adhesion and Adhesives 40, 11-18. Phenolic resins are used in adhesives, coatings, and molding compounds. In this last group, only the soda lignins have a short-term potential for industrial availability. However, phenol-formaldehyde resin may be used for particleboard produced for exterior applications. We manufacture premium Quality Phenol Formaldehyde Resin covering both NOVOLAC and RESOL for Refractory and Foundry Industry. 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. 2012). Lignin powder was slowly added to NaOH solution, keeping the pH of the mixed solution between 12 and 13 for better dissolution of the lignin powder, which was facilitated by vigorous stirring with an overhead stirrer. Lignin as a component in phenol formaldehyde resol resin,” Journal of Applied Polymer Science 33(8), 2915-2924. Resoles are major polymeric resin materials widely used for gluing and bonding building materials. 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. 1997; Alonso et al. Springer Verlag, Berlin Heidleberg New York. 2018). 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. The modeled response surface (Fig. For the free formaldehyde content and solid content, the analysis of variances showed no significant dependence on the studied independent variables. 2011b). Roczniak et al. 2015; Ma et al. 2004). 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. (2007). In industrial practice, there are two basic methods for making the polymer into useful resins. 1 to the Experimental Data for pH (Y1), Gel time (Y2), and Viscosity (Y3), Fig. DOI: 10.1002/app.25098, El Mansouri, N.-E., Yuan, Q., and Huang, F. (2011a). Since formaldehyde exists predominantly in solution as a dynamic equilibrium of methylene glycol oligomers, the concentration of the reactive form of formaldehyde depends on temperature and pH. Some of the lignins that have been used in phenolic resins are derived from annual plants such as flax (Tejado et al. 1994; Alonso et al. The fitted model for the viscosity gave an R2 value of 97.40% and a standard deviation of residuals (SDR) of 37. Yan, T. T., Xu, Y. Q., and Yu, C. W. (2009). The band at 1269 cm-1is attributed to in-plane vibration of C-O of the phenolic group present in PF and LPF. 5) shows that for [S/(P+L)]=1.2 molar ratio, the viscosity increased with increase of lignin content (in lower [F/(P+L)] region) and [F/(P+L)] molar ratio. DOI: 10.1016/j.indcrop.2018.04.027. “Structures, and reactivities with formaldehyde, of some acetosolv pine lignins,” Journal of Wood Chemistry and Technology 19(4), 357-378. DOI: 10.1016/j.eurpolymj.2015.03.029, Roczniak, K., Biernacka, T., and Skarzynski, M. (1983). Results obtained were discussed according to the requirements for adhesives utilization in plywood manufacture, and the optimum operating conditions were selected. Preparation and Characterization of Phenol-Formaldehyde Resins Modified with Alkaline Rice Straw Lignin, Nour-Eddine El Mansouri,b,c,* Qiaolong Yuan,a and Farong Huanga,*, Keywords: Adhesives; Hydroxymethylation; Lignin; Phenol formaldehyde; Wood panels. 2016; Li et al.2018). (2001). “Optimization of experimental variables to modify lignin fromEucalyptus globulus under alkaline catalysis,” BioResources 11(1), 1828-1842. (ed. The first part of the reaction, at around 70 °C, forms a thick reddish-brown tacky material, which is rich in hydroxymethyl and benzylic ether groups. Forss, K. G., and Fuhrmann, A. Gardziella, A., Pilato, L.A., Knop, A. DOI: 10.1016/j.indcrop.2012.10.033, Diop, A., Jradi, K., Daneault, C., and Montplaisir, D. (2015). 2004 and2005; Yang et al. DOI: 10.15376/biores.6.3.2492-2503. The modified lignin from these later methods could partially replace phenol in phenol-formaldehyde resin synthesis. (eds. “Lignins for phenol replacement in novolac-type phenolic formulations, part I: Lignophenolic resins synthesis and characterization,” Journal of Applied Polymer Science 106(4), 2313-2319. The process of polymerizing the compound is completed by adding acidic catalysts like sulfuric acid, oxalic acid, or sulfonic … Table 4. Fig. The reaction was monitored by measuring the viscosity at 25ºC with viscosimeter and halted when the resin viscosities reached 300 to 400 mPas. Hexamethylenetetramine is a hardener added to crosslink novolac. The base material choice depends on the intended application of the finished product. 2004). Higher end billiard balls are made from phenolic resins, as opposed to the polyesters used in less expensive sets. The modified phenol formaldehyde LPF2 and LPF10 with lignin content of 50% and 35%, respectively, were selected to be tested for plywood manufacturing because of their suitable gel time and low free formaldehyde content. In place of phenol itself, they are often produced from cresols (methylphenols). Supplied into the commercial formaldehyde market, it’s also vertically integrated as a raw material into phenolic resin and amino resins production. Synthetic resin bonded paper, made from phenolic resin and paper, is used to make countertops. A slow cure lead to longer pressing time, and therefore the manufacture of the plywood must be expensive. This band, appearing at lower frequency, indicates strong hydrogen bonding occurs. Formaldehyde is to be commercially manufactured on an industrial scale from methanol and air in the presence of a sliver catalyst or the use of a metal oxide catalyst. August 28, 1989 NY Manufacture of phenolic resins; release of phenol and phenolic resin from process vessel; “operator error” cited as cause. Another use of phenolic resins is the making of Duroplast, used in the Trabant automobiles. release of phenol and formaldehyde from process vessel. On the basis of the presented results, it was concluded that the bark of both species can be effectively used as a modifier of PF adhesive. Overall, the viscosity values obtained are between 330 and 790 (mPas), and most of the prepared resins have viscosities within the range of 275to425 (mPas) suitable for use in plywood manufacture (Alonso et al. DOI: 10.1002/app.27003, Vázquez, G., Freire, S., Rodríguez-Bona, C., González, J., and Antorrena, G. (1999). Exterior plywood, oriented strand boards (OSB), engineered laminated composite lumber (LCL) are typical applications. Phenolic laminates are made by impregnating one or more layers of the base material such as paper, fiberglass or carbon with phenolic resin and laminating the resin saturated base material under heat and pressure. The fitted model for pH gave an R2 value of 89.7% and a standard deviation of residuals (SDR) of 0.55. The former of these two gives a complete reaction of oxygen. “Structural modification and characterization of lignosulfonate by a reaction in an alkaline medium for its incorporation into phenolic resins,” Journal of Applied Polymer Science 102(4), 3286-3292.DOI: 10.1002/app.24744, El Mansouri, N. E., Pizzi, A., and Salvado, J. In fact, the incorporation of a large amount of lignin with a high molecular weight is the main reason for increasing the molecular weight of final resin, thus resulting in higher viscosities for lignin-phenol formaldehyde resins. 2016; Tachon et al. Sellers, T, Jr., (1995). for Plastics, Phenolic Resins, Determination of Free Formaldehyde Content by Hydroxylamine Hydrochloride Method. DOI: 10.1016/j.ijadhadh.2015.10.010, Zhang, W., Ma, Y., Xu, Y., Wang, C., and Chu, F. (2013). None reported. The two process are explained in brief below, Manufacture of phenol formaldehyde resin using alkaline catalyst. The Dutch painting forger Han van Meegeren mixed phenol formaldehyde with his oil paints before baking the finished canvas, in order to fake the drying out of the paint over the centuries. “Preparation and performance of lignin-phenol-formaldehyde adhesives,” International Journal of Adhesion and Adhesives64, 163-167. Phenolic laminates are made by impregnating one or more layers of a base material such as paper, fiberglass, or cotton with phenolic resin and laminating the resin-saturated base material under heat and pressure. Under the trade name Bakelite, a phenol-formaldehyde resin was one of the earliest plastics, invented by American industrial chemist Leo Baekeland and patented in 1909. 6. Manufacturer of Resin Plant - Phenolic Resin Plant, Polyester Resin Plant, Phenol Formaldehyde Resin Plant and Resin Manufacturing Plant offered by Vinayak Industries, Thane, Maharashtra. Phenol-formaldehyde (PF) adhesives are frequently used for the production of particular wood-based composites, such as plywood, laminated veneer lumber, glue laminated timber, fiberboard, and particleboard (Malutan et al . Paper phenolics are used in manufacturing electrical components s… The process may be carried out as follows; • A mixture of phenol and formaldehyde are allowed to react in the presence of a catalyst i.e.Oxalic acidandsodium hydroxide. DOI: 10.1016/j.biombioe.2011.02.001, Nada, A. M. A., Elsaied, H., Ibrahem, A. China; b: Laboratory of Biological Engineering, Faculté des Sciences et Téchniques, Sultan Moulay Slimane University (USMS), Mghila BP.523, Béni-Mellal, 23000, Morocco; c: Department of Chemistry, Polydisciplinary Faculty-USMS, Mghila BP.592, Béni-Mellal, 23000, Morocco; * Corresponding authors:elmansouri.noureddine@gmail.com; fhuanglab@ecust.edu.cn. The analysis of variance reported in Table 3, showed that pH was significantly influenced only by (S/PL) at the p=0.05 significance level. The binding agent in normal (organic) brake pads, brake shoes, and clutch discs are phenolic resin. DOI: 10.1016/j.jechem.2017.02.007. Similarly, these bands are also present in LPF with 35% and 50% of lignin. (2008). Previous research findings from Cheng et al. 1. Développement de Nouveaux Adhésifs Bases sur des Dérivés de la Lignine, Ph.D. Dissertation, UMI Dissertation Services. The results obtained for solid content were between 41 and 45%. FTIR spectroscopy was employed to characterize the structure of the lignin raw material and the prepared 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. Different modified phenol formaldehyde resins were prepared and characterized using alkaline rice straw lignin structurally modified by hydroxymethylation reaction. Furthermore, Marbun et al. 2017). The most common application of Phenol-Formaldehyde Resins is in adhesives for bonding wood products, especially those desired for exterior plywood. Article submitted: October 11, 2011; Peer review completed: January 8, 2012; Revised version received and accepted: August 12, 2018; Published: September 7, 2018.
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