This resin is also produced by substituting methylphenols in place of phenols. PF resins are manufactured in batch process. Fernández-Rodríguez, J., Erdocia, X., Sánchez, C., González Alriols, M., and Labidi, J. According to this, LPF2 and LPF10were selected to be tested for plywood manufacturing. DOI: 10.1016/j.ijadhadh.2015.10.010, Zhang, W., Ma, Y., Xu, Y., Wang, C., and Chu, F. (2013). DOI: 10.15376/biores.6.3.2492-2503. One of its important applications is as an adhesive for wood-based panels manufacturing. Bakelite was patented on December 7, 1909. R. S. Skinner, M. T. Skubiak, and D. H. Wetherell. 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. None reported. Phenol formaldehyde resins (PF) or phenolic resins are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. In PF the band at 1474 cm-1 is assigned to -CH- deformation in -CH2– groups. 1 to the Experimental Data for pH (Y1), Gel time (Y2), and Viscosity (Y3), Fig. 2017). 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. Estimated response surface for gel time at [F/(P+L)]=2.2, L(%) vs.[S/(P+L)]. Our formaldehyde (CAS 50-00-0) and urea formaldehyde concentrate 85% are produced via DB Western technology. The molar ratios of sodium hydroxide to phenol-modified alkaline lignin and the formaldehyde to phenol-modified alkaline lignin were from 1.0 to 1.4, and 1.8 to 2.6, respectively. 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. Formaldehyde is made of methanol and phenol from benzene using the cumene process. This band, appearing at lower frequency, indicates strong hydrogen bonding occurs. DOI: 10.1002/app.26941, Tejado, A., Kortaberria, G., Pena, C., Blanco, M., Labidi, J., Echeverria, J. M., and Mondragon, I. 2016; Tachon et al. This is done by reacting resorcinol with formaldehyde. DOI: 10.1016/j.indcrop.2012.10.033, Diop, A., Jradi, K., Daneault, C., and Montplaisir, D. (2015). The fitted model for gel time gave an R2 value of 99.38% and a standard deviation of residuals (SDR) of 0.18. (2007). “Phenolation to improve lignin reactivity toward thermosets application,” ACS Sustainable Chemistry and Engineering 6(4), 5504-5512. Structure of PF resin and lignin (Forss and Fuhrmann 1979). Paper phenolics are used in manufacturing electrical components such as punch-through boards, in household laminates, and in paper composite panels. One reacts phenol and formaldehyde directly to produce a thermosetting network polymer, while the other restricts the formaldehyde to produce a prepolymer known as volcano which can be moulded and then cured with the addition of more formaldehyde and heat. Nimz, H.H. 1. DOI: 10.1002/app.1983.070280209. Hexamethylenetetramine is a hardener added to crosslink novolac. The prepared resins were characterized, and the obtained results were discussed according to the specifications of resins applied for plywood manufacturing. 2014; Podschun et al. 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. This lignin was purified by its treatment with sulfuric acid (1%) several times and washed extensively with hot water to remove the inorganic substances and solubilize the residual sugars (El Mansouri et al.2006 and 2011a).The formaldehyde (35to40% aqueous solution) and phenol (99%), used in this work were purchased from Sigma Aldrich and used as received. “Kraft lignin depolymerization in an ionic liquid without a catalyst,” BioResources 10(3), 4933-4946. DOI: 10.1002/app.29881, Yang, S., Wen, J. L., Yuan, T. Q., and Sun, R. C. (2014). The results obtained for solid content were between 41 and 45%. Among all of the modification treatments that increase reactive sites in lignin, the phenolation and hydroxymethylation modifications are the most studied and effective for formulation of phenolic resins (Nada et al. Another use of phenolic resins is the making of Duroplast, used in the Trabant automobiles. Roczniak et al. Fig. “Use of a methylolated softwood ammonium lignosulfonate as partial substitute of phenol in resol resins manufacture,” Journal of Applied Polymer Science 94(2), 643-650. At this point the resin is a 3-dimensional network, which is typical of polymerised phenolic resins. “Synthesis and characterization of kraft lignin-based epoxy resins,” BioResources 6(3), 2492-2503. DOI: 10.3390/molecules22111850, Tachon, N., Benjelloun-Mlayah, B., and Delmas, M. (2016). July 25, 1989 VA Specialty paper manufacturing; release of phenolic resin and methanol from process vessel. Analysis of Variance for Gel Time, Fig. 1999; Alonso et al. FTIR spectra were recorded with a Nicolet 5700 FTIR-spectrophotometer, using the KBr pellet method. 1997; Alonso et al. 1994; Alonso et al. DOI: 10.1039/C4RA09595B, Zhao, M., Jing, J., Zhu, Y., Yang, X., Wang, X., and Wang, Z. Sellers, T, Jr., (1995). These differences can provide information as to the structure of methylene bridges. Synthetic resin bonded paper, made from phenolic resin and paper, is used to make countertops. 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. 2007, 2008), or kenaf (Yan2009), and agricultural waste such as sugar cane bagasse and wheat straw (Hoareau et al. , Except where otherwise noted, data are given for materials in their, Crosslinking and the formaldehyde/phenol ratio, A. Gardziella, L.A. Pilato, A. Knop, Phenolic Resins: Chemistry, Applications, Standardization, Safety and Ecology, 2nd edition, Springer, 2000. The band at 1018 cm-1 in LPF is characteristic of lignin and is attributed to the C-O of primary alcohol. Our solid RESI-FLAKE ® resins were developed for use in the production of foundry shell molds and cores by the hot-sand process.  The phenolic units are mainly linked by methylene and/or ether groups. The pH requirements for the resol resins were 9.5 or higher. The FTIR spectra of (a) unmodified (PF) and (b) modified (LPF) with L=35% and (c) L=50% are shown in Fig. A suitable gel time of modified phenol formaldehyde resins used for plywood manufacture must be included between 8and10 min. DOI: 10.15376/biores.10.3.4933-4946, El Mansouri, N. E., Farriol, X., and Salvado, J. DOI: 10.1163/1568561054352577, Li, J., Zhang, J., Zhang, S., Gao, Q., Li, J., and Zhang, W. (2018). FTIR spectroscopy analysis showed that the spectra of LPF resins were structurally similar to that of the unmodified PF resin. The resin fully polymerizes (cures) during this process forming the thermoset polymer matrix. Treatment of phenol-formaldehyde resin manufacturing wastewater by the electrocoagulation process February 2012 Desalination and water treatment 39(1-3):176-181 1 injured. Consumers most commonly encounter this substance in the context of a packaged product which includes it, such as MDF, a wood product commonly used in construction. Resoles are referred to as "one step" resins as they cure without a cross linker unlike novolacs, a "two step" resin. Organosolv lignin and modified phenolic resin,” MokuzaiGakkaishi 40(10), 1073-1078. 2000; Zhang et al. The polymerization is brought to completion using acid-catalysis such as sulfuric acid, oxalic acid, hydrochloric acid and rarely, sulfonic acids. DOI: 10.1016/j.indcrop.2017.07.009. Phenol-formaldehyde resins, as a group, are formed by a step-growth polymerization reaction that can be either acid- or base-catalysed. Finally, 10 mL of a hydroxylamine-hydrochloride solution (10%, w/w) was added. 2001; El Mansouri et al. 2004 and2005; Yang et al. The fitted model for the viscosity gave an R2 value of 97.40% and a standard deviation of residuals (SDR) of 37. Figure 6 shows the FTIR-spectrum of lignin raw material used for resins preparation. The base material choice depends on the intended application of the finished product. Phenol formaldehyde resin (resole type) is the most useful thermosetting resin for the manufacture of wood-based panels such as plywood, particleboard, and fiberboard (Nimz 1983; Sellers 1995; Gardziella et al. 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. A., and Yousef, M. A. The bands at 1455 cm-1 and 1425 cm-1 are due to the asymmetric C-H deformation in –OCH3 groups. The partial substitution of phenol by fillers or extenders is one way to reduce the price of these resins. (2006). 1). 2017). 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. DOI: 10.1016/j.jechem.2017.02.007. 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. They were near to the range of values of the commercial resins used for plywood production, which ranges from 45to47% (Alonso et al. By contrast, organosolv lignin, hydrolysis lignin, and soda lignin are produced in minor quantities. The molecular weights are in the low thousands, corresponding to about 10–20 phenol units. Novolaks (or novolacs) are phenol-formaldehyde resins with a formaldehyde to phenol molar ratio of less than one. “Characterization of alkaline lignins for use in phenol-formaldehyde and epoxy resins,” BioResources 6(3), 2647-2662. Formation of phenol-formaldehyde resins. 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 statistical analysis was carried out by using Statgraphics 18 Centurion. Allan, G. G., Dalan, J. 5. “Structures, and reactivities with formaldehyde, of some acetosolv pine lignins,” Journal of Wood Chemistry and Technology 19(4), 357-378. 1989; Peng 1994). The Manufacturing Process A. 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. Used as the basis for Bakelite, PFs were the first commercial synthetic resins (plastics). FTIR spectrum of lignin raw material. In one method, an excess of formaldehyde is reacted with phenol in the … 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). It is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde. 2012). The process of polymerizing the compound is completed by adding acidic catalysts like sulfuric acid, oxalic acid, or sulfonic … The pellets were prepared with a mixture of 300 mg potassium bromide and 5-10 mg of analyzed samples. 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). 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. FTIR-spectra of (a) PF, (b) LPF with L=35% (LPF10), and (c) LPF with L=50% (LPF2). 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. The kettle is kept under continuous agitation. In the LPF the appearance of bonds at 1474 cm-1 and 1450 cm-1 indicates the presence of a methylene bridge. “Isolation and characterization of lignin from the oak wood bioethanol production residue for adhesives,” International Journal of Biological Macromolecules 72, 1056-1062. “Lignin phenol formaldehyde resoles: The impact of lignin type on adhesive properties,” BioResources 11(3), 6727-6741. The used apparatus for gel time determination operates in accordance with ISO 9396 B. “Lignin-based wood adhesives,” in: Pizzi, A. and Duramold. Phenolic resins are found in myriad industrial products. (2016). In place of phenol itself, they are often produced from cresols (methylphenols). The most common application of Phenol-Formaldehyde Resins is in adhesives for bonding wood products, especially those desired for exterior plywood. Encyclopædia Britannica, Inc. 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. “Highly efficient de-polymerization of organosolv lignin using a catalytic hydrothermal process and production of phenolic resins / adhesives with the depolymerized lignin as a substitute for phenol at a high substitution ratio,” Industrial Crops & Products 44, 315-322. 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. Finally, 10 mL of a hydroxylamine-hydrochloride solution (10%, w/w) was added. Lignin is a good candidate to replace phenol in the phenol formaldehyde resins’ formulation because (a) its polyphenolic structure is similar to that of phenolic resin (Fig. Fig. Exterior plywood, oriented strand boards (OSB), engineered laminated composite lumber (LCL) are typical applications. Infrared spectra of lignin-based phenol formaldehyde (LPF) resins showed structural similarity with that of PF resin. Higher end billiard balls are made from phenolic resins, as opposed to the polyesters used in less expensive sets. The higher or lower values indicate a slow or fast curing reaction, respectively. Novolac is a type of formaldehyde phenol resin. studied the effect of benuang (Octomeles sumatrana BN) and duabanga (Duabanga moluccana DB) barks as the filler for phenol-formaldehyde resin (PF) in glulam production. 2016; Li et al.2018). surface materials are transferred to blenders, in which the particles are mixed with resin, wax, and other additives by means of spray nozzles, tubes, or atomizers. “Waste liquors from cellulosic industries.4. Typically, heat and pressure are used to shape and "cure" the mixture into a finished part. The resin fully polymerizes (cures) during this process. The former of these two gives a complete reaction of oxygen. DOI: 10.1002/app.25098, El Mansouri, N.-E., Yuan, Q., and Huang, F. (2011a). The alkaline lignins have been reported to be the most adequate to formulate phenol formaldehyde resins because they are structurally similar to phenol–formaldehyde resins and contain large molecules that allow quick gelation (Forss and Fuhrmann 1979; Allan et al. 1999). Urea-formaldehyde is the resin most commonly used for particleboard manufacture. DOI: 10.1016/j.eurpolymj.2015.03.029, Roczniak, K., Biernacka, T., and Skarzynski, M. (1983). The obtained resins were cooled and stored at lower temperature pending to analysis. At a temperature greater than 90 °C, it forms methylene and dimethylene amino bridges. 2. Ma, Z., Li, S., Qiao, W., and Ren, S. (2016). 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. for Plastics, Phenolic Resins, Determination of Free Formaldehyde Content by Hydroxylamine Hydrochloride Method. 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 . 2011b). “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). Diagram of the experimental protocol. (2006). “Sustainable bio-based phenol-formaldehyde resoles using hydrolytically depolymerized kraft lignin,” Molecules 22(11), 1850. (2017) confirm a similar trend of increasing viscosities of lignin-based phenolic resins with increasing lignin replacement (Cheng et al. Lignin as a component in phenol formaldehyde resol resin,” Journal of Applied Polymer Science 33(8), 2915-2924. The reactive species is the phenoxide anion (C6H5O−) formed by deprotonation of phenol. DOI: 10.1002/app.20887, Alonso, M. V., Oliet, M., Rodriguez, F., Garcia, J., Gilarranz, M. A., and Rodriguez, J. J. DOI: : 10.1016/j.indcrop.2004.04.015, Hu, L., Pan, H., Zhou, Y., and Zhang, M. (2011). Yan, T. T., Xu, Y. Q., and Yu, C. W. (2009). Supplied into the commercial formaldehyde market, it’s also vertically integrated as a raw material into phenolic resin and amino resins production. The same dependency of gel time on lignin content and [S/(P+L)] molar ratio was reported by Alonso and Vázquez (Vázquez et al. This lignin was produced by ShangDong QuanMing Paper Making Co. Ltd. by the alkaline process using sodium hydroxide and Na2CO3from rice straw. Persistence Market Research delivers comprehensive information in the global phenolic resins market, in its latest report, which includes global … Flexural and compressive mechanical properties,” Journal of Applied Polymer Science 107(1), 159-165. The viscosities of both unmodified and modified liquid phenol formaldehyde resol resins were determined using a Brookfield viscosimeter at 30 rpm at 25 °C. Forss, K. G., and Fuhrmann, A. Table 2. 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. Phenolic resins are used in adhesives, coatings, and molding compounds. Phenol-formaldehyde (PF) is a thermosetting resin that is widely used in many fields. Formaldehyde Resin Phenolic Resin Drilling Fluids Filtration Control Agent Phenol Formaldehyde Resin. DOI: 10.1002/app.1987.070330824. “Development and characterization of a lignin-phenol-formaldehyde wood adhesive using coffee bean shell,” Journal of Adhesion Science and Technology 19(6), 493-509.
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