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Melamine Formaldehyde: Curing Studies and Reaction Mechanism

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Melamine Formaldehyde: Curing Studies and Reaction Mechanism Polymer Journal (2013) 45, 413–419 & 2013 The Society of Polymer Science, Japan (SPSJ) All rights reserved 0032-3896/13 www.nature.com/pj ORIGINAL ARTICLE Melamine formaldehyde: curing studies and reaction mechanism Dyana J Merline, Sulafudin Vukusic and Ahmed A Abdala Melamine formaldehyde (MF) resin was synthesized by the reaction between melamine and formaldehyde under alkaline condition in tetrohydrofuran medium with 1:3 melamine to formaldehyde molar ratio. The synthesized resins were characterized by differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR) and thermal gravimetric analysis (TGA). Curing and reaction mechanism was studied by thermal and spectroscopic analysis. Two exothermic peaks were observed in the DSC analysis indicating a two-step crosslinking reaction process was correlated to TGA analysis. FTIR studies at different temperatures explained the two-stage curing mechanism which is concurring with the DSC data. At a temperature range of 140–160 1C, reversible demethylolation is dominating to the crosslinking reaction. At temperature 4160 1C, the crosslinking reaction dominates. On the basis of DSC and FTIR data, a possible crosslinking reaction route was derived and explained. The first stage of curing is the conversion of methylol groups to primary amine and the second stage is the crosslinking of methylol groups to the final product, methylene bridges. The thermal stability of the methylol groups, methylene bridges and the triazine ring, as well as the evaporation of effluents at different stages of curing, are also discussed based on combined TGA and DSC results. Polymer Journal (2013) 45, 413–419; doi:10.1038/pj.2012.162; published online 17 October 2012 Keywords: curing; melamine formaldehyde; thermal properties; thermosetting resin INTRODUCTION profiles during resin preparation.9,10 Thus, curing studies of MF resins Melamine (1, 3, 5-triamino-2, 4, 6-triazine) formaldehyde (MF) is finds immense importance. one of the hardest and stiffest thermosetting polymers, which Several research groups have studied the reaction of melamine with provides good properties and performance. It is an amino resin and formaldehyde. Studies on the addition reaction between melamine has various material advantages, such as transparency, better hardness, and formaldehyde by means of reversed-phase liquid chromatography thermal stability, excellent boil resistance, scratch resistance, abrasion has been reported.11 All of the nine methylol melamines could be resistance, flame retardant, moisture resistance and surface smooth- assigned and the technique can also be applied to the quantitative ness, which lead MF to large industrial applications.1 These polymers analysis of methylol melamines in the reaction mixtures. Several were originally used as wood adhesives and have now found appli- authors12–14 have studied the reactions and structures of soluble MF cations in flooring and decorative laminates, molding compounds, resins by means of 13C nuclear magnetic resonance (NMR). The coatings and adhesives.2,3,4 MF resins are incorporated in wide variety structure elucidation of melamine–formaldehyde–polyvinylpyrrolidone of products that are valued for its toughness and relative ease of by 1HNMRand13C NMR has been reported.15 The methylol, manufacture.5 The curing behavior and the degree of crosslinking methylene and methylene ether structures were assigned. Several of MF resin determine the tailored product properties such as studies on the kinetics of the addition reaction between melamine mechanical, thermal and electrical properties.6 Cured MF polymers and formaldehyde in aqueous phase during the initial stage of resin are sufficiently hard and exhibit high resistance against temperature, formation have also been explained.11,16,17 chemicals and hydrolysis, making them suitable for interior working Cured resins are, because of their insolubility, more difficult surfaces.7 If the resin is not cured properly, MF will lack mechanical to characterize chemically. Cross-polarization magic angle spinning strength and surface finishes. For example, MF impregnated papers (CP-MAS) 13CNMR,CP-MAS15N NMR and Fourier transform will lack hardness, durability, brilliance and resistance to hydrolysis infrared spectroscopy (FTIR) spectroscopy have already been utilized and chemical agents.8 The condensation reaction and the resulting for the investigation of the chemical reactions that occur during structure of MF resins vary significantly with the reaction conditions condensation. Curing studies of MF resins by high-resolution solid such as molar ratios of the reactants, pH and reaction temperature state 13C NMR spectra indicate the conversion of free methylo1 Department of Chemical Engineering, The Petroleum Institute, Abu Dhabi, UAE Correspondence: Dr AA Abdala, Department of Chemical Engineering, The Petroleum Institute, PO Box 2533, Abu Dhabi 2533, UAE. E-mail: [email protected] Received 8 April 2012; revised 9 July 2012; accepted 12 July 2012; published online 17 October 2012 Curing of melamine formaldehyde DJ Merline et al 414 groups to methylene linkages throughout curing. However, the to characterize chemically. Even though the curing processes of MF methylene ether links overlap with the residual methylol groups, so resins are well understood on an empirical basis, there is scope for it is not clear from these spectra whether or not there are many methods that will provide a more detailed understanding of the residual unreacted methylol groups.13,8 Information concerning the chemical reactions that occur during condensation. Research work relative proportions of methylol groups, methylene and methylene that has been carried out so far mainly explains the elucidation of ether linkages could be obtained more rapidly from CP-MAS 13C methylolmelamines and its reaction path. Only few attempts have NMR. FTIR spectroscopy has been shown to have only limited been done on the crosslinking reaction mechanism. The crosslinking capabilities in this regard due to the high number of slightly different reaction of MF resin in water that leads to the formation of ether structures in the MF resins which result in very broad and overlapping bridge has been explained.31 The crosslinking mechanism of fully absorption bands.18 Thermogravimetry/infrared coupling analysis has alkylated and partially alkylated MF resin with catalyst has been also been carried out to determine the effluents during the curing studied by Blank.32 Author found the mechanism by analyzing the process.19–21 MF polycondensate with high molecular weight and volatiles formed during the crosslinking reaction by gas chromato- high processing thermostability was prepared with variable melamine: graphy. Specific acid catalyst was found to be the catalyzing mecha- formaldehyde ratios ranging from 1:1.33 to 1:4, which acts as the nism for fully alkylated MF resin, whereas for the partially alkylated formaldehyde absorbent by the addition reaction of the hydrogen MF resin, the level of formaldehyde content in the reaction volatiles on the amine groups with the formaldehyde produced by the indicated a demethylolation and subsequent catalysis was found to decomposition of polyoxymethylene under oxygen and heat.22 be the crosslinking mechanism. Anderson et al.33 studied the initial Lower crosslinking degree of MF polycondensate was observed at methylolation and the subsequent thermally induced condensation lower formaldehyde ratio (melamine: formaldehyde ratio of 1: 1.33), reaction involves the formation of ether links that readily decomposes which was unstable and decomposed during the thermal weight loss into methylene link at above 135 1C and this reaction sequence is also analysis. On the other hand, at very high formaldehyde content, the accompanied by a demethylolation yielding free amine. Still studies unreacted hydrogen on the MF molecules was not sufficient to have are progressing to find a complete reaction mechanism of MF resin. the role as formaldehyde absorbent of polyoxymethylene. Even though the reversible demethylolation occurring during the cure The MF resin formation consists of two stages: methylolation reaction of MF resin has been cited with the presence of a catalyst and and condensation. The first attempt to investigate the methylolation without the presence of a catalyst, still there is no clear idea at what and condensation reactions was by Okano and Ogata.9 In the first temperature range demethylolation dominates to the crosslinking step of methylolation reaction, melamine reacts with formaldehyde reaction and also the temperature where crosslinking reaction producing a series of nine distinct methylol melamine from mono- dominates to demethylolation for a pure non-alkylated MF resin. hexamethylol melamine. The second step of condensation reaction Even though many research works have been done so far related to leads to the formation of large number of different oligomers the curing studies of MF, we proposed clarity in the reaction containing methylene and methylene ether bridges.4,8,10,23,24 mechanism by thermal and spectroscopic tools that simplify the The ratio of formation of two bridges during condensation reaction doubts of MF reaction stages, temperatures and the reaction route. depends on the pH of the reaction medium. If the pH is relatively low, Nowhere in the literature explains the two exothermic peaks observed 7–8, methylene bridges dominate whereas at high pH values above 9, in differential scanning calorimetry (DSC), even though
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