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phenol formaldehyde resin manufacturing process

02 12 2020

“Lignin-based polycondensation resins for wood adhesives,” Journal of Applied Polymer Science 103(3), 1690-1699. Phenolic Resins: Chemistry, Applications, Standardization, Safety and Ecology. 6. Liquid RESI-SHELL ® resins are used in the production of foundry shell molds and cores by the warm air sand process. 2015; Ma et al. Norm ISO 9397. The higher or lower values indicate a slow or fast curing reaction, respectively. DOI: 10.1002/app.20887, Alonso, M. V., Oliet, M., Rodriguez, F., Garcia, J., Gilarranz, M. A., and Rodriguez, J. J. However, phenol-formaldehyde resin may be used for particleboard produced for exterior applications. Previous research findings from Cheng et al. Table 2 lists the results of fitting the data for pH (Y1), gel time (Y2) and viscosity (Y3) with polynomials of the form (Eq. 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. 2016; Tachon et al. DOI: 10.15376/biores.6.3.3515-3525, Hoareau, W., Oliveira, F. B., Grelier, S., Siegmund, B., Frollini, E., and Castellan, A. Faix, O. DOI: 10.15376/biores.10.3.4933-4946, El Mansouri, N. E., Farriol, X., and Salvado, J. “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. Phenolic resins are used in adhesives, coatings, and molding compounds. (2001). Forss, K. G., and Fuhrmann, A. The base material choice depends on the intended application of the finished product. Phenol-formaldehyde resin is "like" a one-way street; once formed, it cannot be turned back into the starting points & get additives from it according to our present knowledge. Structure of PF resin and lignin (Forss and Fuhrmann 1979). “Modification of lignins for use in phenolic resins,” ACS Symposium Series 385, 55-67. The obtained resins were cooled and stored at lower temperature pending to analysis. POLYTONETM PF 132 C is a phenol – formaldehyde resin to be mixed with Hexa or Part 2 Catalyst.POLYTONETM PF 132 C (Part 1 + 2) effortlessly penetrates and adheres to the structure of many organic and inorganic fillers and reinforcements which makes it an ideal candidate for various end uses. “Optimization of experimental variables to modify lignin fromEucalyptus globulus under alkaline catalysis,” BioResources 11(1), 1828-1842. “Structure-property relationships for technical lignins for the production of lignin-phenol-formaldehyde resins,” Industrial Crops and Products 108, 316-326. A test tube equipped with a plunger was filled with 10 g of unmodified and modified phenolic resins and then placed in an oil bath under a constant temperature of 130°C.The resin was mixed at short time intervals and the gel point was reached when the plunger could not be moved up. “The isolation and characterization of lignin of kenaf fiber,” Journal of Applied Polymer Science 114(3), 1896-1901. Lignin–Adhesive Research for Wood Composites, Forest and Wildlife Research Center. Mancera, C., Ferrando, F., Salvado, J., and El Mansouri, N. E. (2011). 7. The modified lignin from these later methods could partially replace phenol in phenol-formaldehyde resin synthesis. 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%. Diagram of the experimental protocol. 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. The pH requirements for the resol resins were 9.5 or higher. (2017) confirm a similar trend of increasing viscosities of lignin-based phenolic resins with increasing lignin replacement (Cheng et al. DOI: 10.1002/app.29881, Yang, S., Wen, J. L., Yuan, T. Q., and Sun, R. C. (2014). 2016; Norambuena et al. 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. 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. This is why novolacs (F:P <1) do not harden without the addition of a crosslinking agents, and why resoles with the formula F:P >1 will. “Waste liquors from cellulosic industries.4. “Fourier transform infrared spectroscopy,” in: Methods in Lignin Chemistry, Li n, S.Y., and Dence, C. W. (2013) and Siddiqui et al. DOI: : 10.1016/j.indcrop.2004.04.015, Hu, L., Pan, H., Zhou, Y., and Zhang, M. (2011). In one method, an excess of formaldehyde is reacted with phenol in the … Novolaks (or novolacs) are phenol-formaldehyde resins with a formaldehyde to phenol molar ratio of less than one. The same dependency of gel time on lignin content and [S/(P+L)] molar ratio was reported by Alonso and Vázquez (Vázquez et al. Available Variants : Resin for Magnesia-Carbon Bricks - PROREZ 7015; Resin for Blast Furnace Tap-hole Mass - PROLAC ABC The used apparatus for gel time determination operates in accordance with ISO 9396 B. The resin fully polymerizes (cures) during this process forming the thermoset polymer matrix. 2017). Fernández-Rodríguez, J., Erdocia, X., Sánchez, C., González Alriols, M., and Labidi, J. Results of Fitting Eq. “Organosolv wheat straw lignin as a phenol substitute for green phenolic resins,” BioResources 11(3), 5797-5815. Elements. 1 Introduction . 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. Podschun, J., Saake, B., and Lehnen, R. (2015). ), Wood Adhesives Chemistry and Technology, Marcel Dekker, New York, pp. 2016; Li et al.2018). DOI:10.1016/j.ijbiomac.2014.10.020, Khan, M. A., and Ashraf, S. M. (2005). 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. Our formaldehyde (CAS 50-00-0) and urea formaldehyde concentrate 85% are produced via DB Western technology. DOI: 10.15376/biores.6.3.2647-2662, El Mansouri, N.-E., Yuan, Q., and Huang, F. (2011b). 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. 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. DOI: 10.1016/j.indcrop.2017.07.009. 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. This variable is of interest because of its influence on the resin storage life. However the second type of catalyst achieves almost complete methanol conversion. “Sustainable bio-based phenol-formaldehyde resoles using hydrolytically depolymerized kraft lignin,” Molecules 22(11), 1850. This is done by reacting resorcinol with formaldehyde. 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. By contrast, organosolv lignin, hydrolysis lignin, and soda lignin are produced in minor quantities. DOI: 10.1163/1568561054352577, Li, J., Zhang, J., Zhang, S., Gao, Q., Li, J., and Zhang, W. (2018). 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. 1989; Sellers et al. The molecular weights are in the low thousands, corresponding to about 10–20 phenol units. 2000; Zhang et al. 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. The results obtained for solid content were between 41 and 45%. FTIR spectra were recorded with a Nicolet 5700 FTIR-spectrophotometer, using the KBr pellet method. The kettle is kept under continuous agitation. 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 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. When formaldehyde is used in excess, it is very difficult to reach low values of free formaldehyde in the formulation of lignin-phenol formaldehyde resole resins. 1999; Alonso et al. (2006). This resin has good chemical resistance, electrical insulation, and dimensional stability, but the price and environmental concerns may limit usage in some applications. (1997). 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. 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. Obtained polymer is thermoplastic and require a curing agent or hardener to form a thermoset. The band at 1018 cm-1 in LPF is characteristic of lignin and is attributed to the C-O of primary alcohol. Novolac is a type of formaldehyde phenol resin. 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. Analysis of Variance for Gel Time, 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. A very fast cure can cause the lost of the final properties of the board. Estimated response surface for gel time at [F/(P+L)]=2.2, L(%) vs.[S/(P+L)]. 2015; Jiang et al. This band, appearing at lower frequency, indicates strong hydrogen bonding occurs. (2016). At a temperature greater than 90 °C, it forms methylene and dimethylene amino bridges. Paper phenolics are used in manufacturing electrical components such as punch-through boards, in household laminates, and in paper composite panels. R. S. Skinner, M. T. Skubiak, and D. H. Wetherell. The first reaction gives a methylene bridge, and the second forms an ether bridge: The diphenol (HOC6H4)2CH2 (sometimes called a "dimer") is called bisphenol F, which is an important monomer in the production of epoxy resins. [7], 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. This resin is also produced by substituting methylphenols in place of phenols. They are formed through the reaction of phenol with formaldehyde, followed by cross-linking of the polymeric chains. Bands at 2937 cm-1 and 2846 cm-1 are the consequence of in-plane and out-of-plane stretching of aliphatic -CH2-. (1987). DOI: 10.1016/j.biombioe.2011.02.001, Nada, A. M. A., Elsaied, H., Ibrahem, A. All rights reserved. However, there has been little research published on the preparation and characterization of phenol formaldehyde resin using alkaline rice straw lignin. DOI: 10.1002/app.26941, Tejado, A., Kortaberria, G., Pena, C., Blanco, M., Labidi, J., Echeverria, J. M., and Mondragon, I. DOI: 10.15376/biores.11.3.5797-5815, Tejado, A., Kortaberria, G., Pena, C., Labidi, J., Echeverria, J. M., and Mondragon, I. DOI: 10.1016/j.ijadhadh.2012.08.004. Experimental Conditions and Properties of Synthesized Modified Phenol Formaldehyde Resins. “Some properties and chemical-structure of phenolic resins and their derivatives,” Journal of Applied Polymer Science 28(2), 531-542. One of its important applications is as an adhesive for wood-based panels manufacturing. A molar ratio of NaOH to lignin of 0.8 was used, which resulted in a final pH of 12.3. 2013; Zhao et al. The bands at 1455 cm-1 and 1425 cm-1 are due to the asymmetric C-H deformation in –OCH3 groups. 2016). The reactive species is the phenoxide anion (C6H5O−) formed by deprotonation of phenol. 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. 2004; Vishtal and Kraslawski 2011). Persistence Market Research delivers comprehensive information in the global phenolic resins market, in its latest report, which includes global … Novolacs have multiple uses as tire tackifier, high temperature resin, binder for carbon bonded refractories, carbon brakes, photoresists and as a curing agent for epoxy resins. This product is used in a wide variety of settings and industries, and is one of the oldest synthetic resins around. The acquisition conditions were: spectral width of 4000to400 cm-1, 32 accumulations, and 4-cm-1 resolution. However, modified resins with gel time near to 10min can be considered and tested for plywood manufacturing if they present low free formaldehyde content. Table 4. 2014; Podschun et al. Ma, Z., Li, S., Qiao, W., and Ren, S. (2016). “Lignins for phenol replacement in novolac-type phenolic formulations. 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. Results obtained were discussed according to the requirements for adhesives utilization in plywood manufacture, and the optimum operating conditions were selected. DOI: 10.15376/biores.11.3.6727-6741, Gosselink, R. J. Treatment of phenol-formaldehyde resin manufacturing wastewater by the electrocoagulation process February 2012 Desalination and water treatment 39(1-3):176-181 5. These differences can provide information as to the structure of methylene bridges. (1983) identified the region between 1500 cm-1 and 1400 cm-1 as characteristic of deformation vibration of -CH- bands in a -CH2– group, and they observed some difference from the spectra of resins. The modeled response surface (Fig. Resoles are referred to as "one step" resins as they cure without a cross linker unlike novolacs, a "two step" resin. 2011b). 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. This lignin was produced by ShangDong QuanMing Paper Making Co. Ltd. by the alkaline process using sodium hydroxide and Na2CO3from rice straw. “Reactivity enhancement of organosolv lignin by phenolation for improved bio-based thermosets,” European Polymer Journal, 67, 1-11. DOI: 10.15376/biores.6.3.2492-2503. 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. Typically, heat and pressure are used to shape and "cure" the mixture into a finished part. Siddiqui, H., Mahmood, N., Yuan, Z., Crapulli, F., Dessbesell, L., Rizkalla, A., Ray, A., and Xu, C. (2017). (2008). 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. DOI: 10.1002/app.1983.070280209. “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). FTIR spectrum of lignin raw material. The fitted model for the viscosity gave an R2 value of 97.40% and a standard deviation of residuals (SDR) of 37. “Lignocellulosic ethanol residue-based lignin-phenol-formaldehyde resin adhesive,” International Journal of Adhesion and Adhesives 40, 11-18. 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. The statistical analysis was carried out by using Statgraphics 18 Centurion. When the molar ratio of formaldehyde:phenol reaches one, in theory every phenol is linked together via methylene bridges, generating one single molecule, and the system is entirely crosslinked. The Manufacturing Process A. The fitted model for pH gave an R2 value of 89.7% and a standard deviation of residuals (SDR) of 0.55. Analysis of variance (Table 5) showed that viscosity was significantly influenced by all the studied parameters, and the cross-terms (L(%))*[F/(P+L)] and[F/(P+L)]*[S/(P+L)] at the p=0.05 significance level. 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. 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. 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. 10.1021/bk-1989-0385.ch005, Alonso, M. V., Rodriguez, J. J., Oliet, M., Rodriguez, F., Garcia, J., and Gilarranz, M. A. 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. Table 2. Sometimes people select fibre reinforced phenolic resin parts because their coefficient of thermal expansion closely matches that of the aluminium used for other parts of a system, as in early computer systems[4] 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. Table 5.Analysis of Variance for Viscosity at 25 °C, Fig. (eds. (1992). Figure 6 shows the FTIR-spectrum of lignin raw material used for resins preparation. Some of the lignins that have been used in phenolic resins are derived from annual plants such as flax (Tejado et al. (2017). Formation of phenol-formaldehyde resins. 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). It was developed by the Belgian-American chemist Leo Baekeland in Yonkers, New York, in 1907. 2016). Synthetic resin bonded paper, made from phenolic resin and paper, is used to make countertops. 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 . 2004 and2005; Yang et al. Phenolic resins are also used for making exterior plywood commonly known as weather and boil proof (WBP) plywood because phenolic resins have no melting point but only a decomposing point in the temperature zone of 220 °C (428 °F) and above. (1983). The gel time is an important parameter to take into consideration when resins are formulated, because it determines the resins reactivities. 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.

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