Reactive Polymers Fundamentals and Applications || Melamine Resins

6 Melamine Resins

Melamine resins rely on 1,3,5-triazine-2,4,6-triamine and formaldehyde. They are similar tourea/formaldehyde polymers.

6.1 History

The industrial use of melamine resin started in thelate 1930s when the Swiss company CIBA beganthe industrial production of melamine from dicyandi-amide [1,2]. Earlier, the use of this resin was limitedbecause of its high price. Now melamine can be pro-duced cheaper from urea, so the economical situationis improved.

6.2 Monomers

6.2.1 MelamineMelamine may be partially or totally replacedwith other suitable amine-containing compounds.Alternatives to melamine include urea, thiourea,diyandiamide, 2,5,8-triamino-1,3,4,6,7,9,9b-hepta-azaphenalene (melem), (N-4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine (melam), melon,ammeline, ammelide, substituted melamines, andguanamines [3]. The melamine homologs melam,melem, and melon have higher thermal stability thanpure melamine. These compounds are also used asflame retardants.

Substituted melamines include alkyl melaminesand aryl melamines. Representative examplesof some alkyl-substituted melamines includemethylmelamine, dimethylmelamine, trimethyl-melamine, ethylmelamine, and 1-methyl-3-propyl-5-butylmelamine. Typical examples of anaryl-substituted melamine are phenylmelamine ordiphenylmelamine. Melamine and related com-pounds are shown in Figure 6.1. Foams and fibersexhibit increased elasticity when some of themelamine is replaced by a substituted melamine,e.g., N-mono-, N ,N ′-bis-, and N ,N ′,N ′′-tris(5-hydroxy-3-oxapentyl)melamine [4]. However, basedon considerations of cost and availability, standardmelamine is generally preferred.

N N

NH2N NH2

Benzoguanamine

C

N

N NCN

H

HH

H H

Dicyandiamide

N

N

N N

N

N N

NH2

NH2H2N

Melem Melon

n

N

N

N N

N

N N

NH2

NHH2N

N N

N

NH2

H2N NH2

Melamine Melam

N N

N

NH2

NH2

H

NH2N

NH2

N

NN

Figure 6.1 Melamine, melam, melem, melon, ben-zoguanamine, dicyandiamide.

6.2.2 Other ModifiersSuitable resin modifiers are ethylene diamine, mela-mine, ethylene ureas, and primary, secondary, andtertiary amines. Dicyandiamide can also be incorpo-rated into the resin.

The concentrations of these modifiers in the reac-tion mixture may vary typically from 0.05% to5.00%. All these modifiers promote hydrolysis resis-tance, polymer flexibility, and lower formaldehydeemissions [5].

6.2.3 SynthesisSimilar to urea, melamine reacts with formaldehyde inweakly alkaline aqueous media to form methylol com-pounds. Melamine is hexafunctional, so up to hexa-methylol monomers can be formed. Hexamethylolmelamine is shown in Figure 6.2.

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194 REACTIVE POLYMERS FUNDAMENTALS AND APPLICATIONS

N N

N N

N

N

CH2OH

CH2OH

CH2OH

HOH2C

HOH2C

HOH2C

+N N

N

NH2

H2N NH2

H2C O

Figure 6.2 Hexamethylol melamine from melamineand formaldehyde.

Further condensation proceeds under neutral andacidic conditions, thereby forming methylene ordimethylene ether bonds. A pure melamine resin gelswithin a few days at room temperature. Because ofthis undesired property, melamine resins are blendedwith urea resins.

6.2.3.1 Etherified ResinsEtherified resins are prepared by the reactionof melamine with formaldehyde under the conditionsof pH around 6 and reflux temperature in the pres-ence of a large amount of butanol. Xylene cyclesout the water formed by the condensation reactionby azeotropic distillation and accelerates the etherifi-cation in this way.

6.2.4 ManufactureMelamine is mixed with neutralized formaldehydesolution. The excess of formaldehyde is about three-fold. The mixture is heated to 75–85 ◦C. When thesolution becomes cloudy, water is admixed. Thenfillers can be admixed for molding resins. The mixtureis dried at 70–80 ◦C, while the condensation reactionstill proceeds.

In the co-condensation of melamine and urea, due tothe difference in the reactivity of melamine and urea,the condensation of the melamine moiety is quickerthan that of the urea moiety.

The crosslinking of a mixture of novolak andmelamine resins under pressure was investigated. The

use of pressure to the reaction vessel favors the for-mation of a more structured crosslinked resin. Thisenhances the thermal stability [6]. The crosslinkingessentially occurs in two stages. At 150 ◦C a networkis formed that is composed of disubstituted and trisub-stituted phenols without significant reaction with themelamine moieties. Then at 200 ◦C, a direct crosslink-ing of melamine polymers with the disubstituted phe-nols occurs [7].

6.3 Special Additives

6.3.1 Reinforcing MaterialsJute fiber-reinforced melamine composites with afiber content of 16–35% were prepared by hot press-ing at 125 ◦C for 10 min under pressure [8].

The mechanical properties are shown in Table 6.1.The effect of gamma radiation on the composites

was investigated. The water uptake of the irradiatedcomposites was found to be improved. The adhesionof the fiber to the matrix was found to be quite good.

6.3.2 Flame RetardantsCombinations of melamine resins with other com-pounds have been used as flame retardants forother polymers. For example, bis(2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-methanol)melami-nium salt and microcapsules therefrom with amelamine resin shell have been used as flameretardants for epoxy resins [9].

N-Methylol dimethylphosphonopropionamide incombination with a melamine resin, phosphoric acid,and zinc oxide can be used to impart flame retardancyinto cotton fabrics [10]. A flame ignited on the treatedfabrics extinguishes right after the removal of theignition source. The addition of zinc oxide increasesthe stability. Flame retardancy is still observed evenafter 10 home laundering cycles. A treatment withplasma of the cotton fabrics before the introduction

Table 6.1 Mechanical Properties of Jute Fiber-reinforced Melamine Composites [8]

Property Value

Tensile strength 44 MPaTensile modulus 532 MPaBending strength 112 MPaBending modulus 1.4 GPaImpact strength 13 kJ m−2

6: MELAMINE RESINS 195

of the flame retardant can still improve the properties[11,12].

Flame retardants for poly(propylene) are tris(2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-oxo-4-meth-anol) phosphate as such and microencapsulated ina melamine resin shell. The limited oxygen indexvalues of the microencapsulated composites arehigher than those with the neat flame retardant[13]. This flame retardant is also of value for epoxyresins [14].

6.3.3 RecyclingPaper wastes from the edge trimming of partiallycured, dried papers were suggested for use as a binderfor the light medium fiberboard materials [15]. Thepanels were prepared from various mixtures of thesoftwood fiber and hammer-milled impregnated paperwaste. The dimensional stability and the mechani-cal properties of the panels were improved by addinghammer-milled melamine impregnated paper waste.Further, better dimensional stability was monitored.

It has been proposed to produce bioethanol fromlignocellulosics by an alkali pretreatment and subse-quent enzymic saccharification [16]. Low-cost mate-rials must be used in order to reduce the costs ofproduction. In the case of plywood, an alkali pretreat-ment removes most of the phenol resin which maybe included in the plywood. In this case, the enzymicsaccharification of plywood pulp proceeds smoothly,and reasonable glucose yields are obtained. However,if the particleboards contain a melamine urea resin,small resin particles may remain in the pulp and thenhinder the enzymic saccharification. In this case, theglucose yield from the particleboards may be less than50% in comparison to favorable conditions.

Melamine/formaldehyde resins contain high con-centrations of nitrogen and, if properly composted,can yield valuable products. The effects of startercompost, nutrients, gypsum, and microbial inocu-lation on composting of paint sludge containingmelamine resin were investigated [17].

A composting experiment was conducted at 55 ◦Cfor 91 days and then at 30 ◦C for another 56 days.After 91 days, the composts were already inocu-lated with a mixed population of melamine-degradingmicroorganisms.

After the whole duration of 147 days ofcomposting, the extent of degradation was 73–95%for treatments with inoculation of microorganisms

in comparison to 55–74% for treatments withoutinoculation. In addition, the degradation is enhancedby nutrients and gypsum. The experiments revealedthat composting of melamine resins on a large scaleis possible [17].

6.3.3.1 ChipboardsIncreasing amounts of agricultural waste residuesare produced with an enormous potential for indus-trial crops and products. Sugarcane bagasse has beenexamined for the production of chipboard panels[18]. Suitable binders are urea/formaldehyde andmelamine/formaldehyde resins. In addition to sug-arcane bagasse, pine or eucalyptus particles andoptionally paraffin are used in the formulation. Thefabricated panels comply mostly with the AmericanStandard CS 236-66.

6.3.3.2 Nitrogen RemovalThe wood industry produces huge amounts of woodwaste containing various additives. Particleboards andlaminated flooring constitute a resource of energy.However, this type of waste needs a refinement toeliminate the bounded nitrogen which is responsiblefor the formation of pollutants during thermal ener-getic recycling [19].

The thermal behavior of wood board contain-ing urea/formaldehyde and melamine/formaldehyderesins indicates that the chemically bound nitrogencan be removed by a low-temperature pyrolysis at250–300 ◦C [20].

Actually, the temperature range of decompositionof wood is different from those of the resins. Kineticmodels establish that the degradation of the compo-nents of the wood board composition influences eachother.

The efficiency of the removal of nitrogen by thethermal treatment can be characterized by elementalanalysis and in terms of energy recovery. Some 70%of the initial nitrogen can be removed from the waste.Further, the temperature of treatment does not influ-ence the efficiency. However, the energy efficiency ishighest at the lowest possible temperature of thermaltreatment.

6.4 Properties

Phenol/formaldehyde resins and melamine/formal-dehyde resins are standard resins used for many


products. The choice of resin depends on the desiredproperties. Phenol/formaldehyde resins are strong anddurable and relatively inexpensive, but are generallycolored resins. Melamine resins are water clear but aremore expensive. They are generally used for prod-ucts where the color or pattern of the substrate isretained with a transparent melamine protective coat-ing or binder.

The emission of formaldehyde in melamine/urea/formaldehyde resins decreases as the melamine con-tent is increased [21]. This is explained due tothe stronger bonding between triazine carbons ofmelamine than those of urea carbons. Sulfonatedmelamine/formaldehyde resins exhibit good solubil-ity in water [22].

The ratio of formaldehyde to urea and themelamine content governs the hydrolytic stability ofa urea/melamine/formaldehyde resin. In experiments,the hydrolytic stability of such a cured resin was mea-sured by the mass loss and the amount of formalde-hyde set free after the acid-induced hydrolysis [23].A high ratio of formaldehyde to urea and a highmelamine content decreases the hydrolytic stability.This can be explained by a more branched networkstructure which favors the susceptibility toward acidhydrolysis.

6.5 Applications and Uses

Melamine-based resins are widely used as adhesivesfor wood, as resins for decorative laminates, var-nish, and moldings, and for improving the proper-ties of paper and cellulosic textiles. In comparisonto urea/formaldehyde resins, a melamine-based resinhas higher resistance against heat and moisture.

Etherified melamine resins are often used in com-bination with alkyd resins for production of decora-tive laminates. Modification of textiles by melamineis used to impart crease resistance and shrinkage. Thewet strength of paper is greatly improved by the useof melamine resins as wet-end additives.

Acoustic ceiling tiles are backcoated withmelamine resins in order to make them more rigidand humidity-resistant when installed in suspendedceilings. Melamine resins are also used for the prepa-ration of decorative or overlay paper laminates. Thisapplication is due to their excellent color, hardness,and solvent, water, and chemical resistance, heatresistance, and humidity resistance.

Molded articles, such as dinnerware, are preparedwith a combination of melamine/formaldehyde resinsand urea/formaldehyde resins. The resins are com-bined because the melamine/formaldehyde resin istoo expensive by itself. Such articles made from theseresins are generally not very water-resistant or dimen-sionally stable [5].

6.5.1 Wood ImpregnationMelamine/formaldehyde (MF) is one of the hardestand stiffest isotropic polymeric materials used fordecorative laminates, molding compounds, adhesives,coatings, and other products. Due to the high hardnessand stiffness, and low flammability, MF resins can beused to improve the properties of solid wood. An MFresin can penetrate the amorphous region of wood. Ithas been established that significant portions of a suit-able MF resin penetrate the secondary cell wall layersand middle lamella of softwoods [24].

The dimensional stability, mechanical properties,and the fire resistance of the wood from Cryptome-ria fortunei can be improved by adding a melamineurea/formaldehyde resin and boric acid/borax [25].Both types of impregnation exhibit good permeabil-ity to wood. This treatment can effectively enhancethe dimensional stability and the fire resistance of thewood materials.

The durable properties of plywood in a modifiedUF resin were investigated using ammonium chlorideas curing catalyst and different ratios of melamineto urea. The melamine content does not change theproperties itself; however, the influence of the curingcatalysts can be minimized by adding melamine to theformulation [26].

The anti-swelling properties of southern pine woodwhich was treated with poly(vinyl alcohol) (PVA)or melamine or urethane were evaluated. The water-repellency efficiency of melamine and PVA-treatedwafers exhibited values 80% superior to untreatedwafers [27].

The photo-yellowing of native and poly(ethyleneglycol) (PEG) modified wood and wood/melamineresin composites was studied [28]. The discolorationshows a systematic asymptotic trend toward highervalues with increasing time of irradiation. Theyellowing proceeds faster in natural wood as inwood/melamine resin composites. The discolorationcan be significantly reduced with PEG, depending onthe molecular weight of PEG. PEG shows a shift to


red, whereas melamine effects a yellow shift on irra-diation. Both effects result in a decreased yellowing.

6.5.2 Waste Water CleaningA melamine/formaldehyde/urea resin was used asadsorbent to clean waste waters. Methylene blue wasused to simulate leather and textile processing dyes.Spectroscopic methods were used to measure theabsorbance and thus removed amounts of dye. Fur-ther, parameters such as pH and contact time wereoptimized. The capacity of the sorbent for the dye wasfound to follow a Langmuir isotherm. The optimal pHfor adsorption is 7–8. The mechanisms of adsorptionare believed to proceed by a cation exchange of methy-lene blue with the carboxylic groups of the resin [29].

6.5.3 Separation of Metal IonsMelamine resins were modified with either thioureaor tetraoxalyl ethylenediamine. The adsorption of theresins for Ag+ and Cu2+ in aqueous solutions wasexamined [30].

The thiourea modified resin shows a high selec-tivity for Ag+ in aqueous solutions of Cu2+, whilethe tetraoxalyl ethylenediamine modified resin showsa reverse behavior. The kinetics of the adsorption ofAg+ by the thiourea modified resin fits a pseudo-first-order model. In contrast, the adsorption of Cu2+ bythe tetraoxalyl ethylenediamine modified resin fits apseudo-second-order model.

The mechanism of adsorption is believed to be achelation reaction. The tests indicate that the resinscan be used repeatedly [30].

6.6 Special Formulations

6.6.1 CoatingsMelamine resin polymers exhibit high transmittance,high pencil hardness, and a high refractive index.However, long reaction times at high temperatures arerequired to obtain the final condensation products. Analterative is to modify the resins with acrylics [31].These modified melamine resins can be cured rapidlydue to the radical reaction of the acrylic groups andthey retain their high transparency and high refractiveindex. Further, low shrinkage is observed.

In acrylic/melamine clear-coat compositions it wasfound that the presence of nanosilica particles reduces

the activation energy of cure and increases the totalheat of reaction [32].

Also, waterborne coating formulations can be curedquickly using an acrylic emulsion as the major coat-ing constituent and a highly reactive melamine resin ascuring agent [33]. The performance of the cured coat-ings has been tested according to standard methods.Dry heat resistance, wet heat resistance, adhesion,pencil hardness, and stain resistance meet the require-ments. A suggested usage is for decorative paper sur-faces.

The effects of various biological compounds onan automotive acrylic/melamine clear-coat that isapplied over silver and black basecoats have been doc-umented. It was found that pancreatin and bird drop-pings influence the coating systems more severelycompared to natural and synthetic arabic gums [34].It has been shown that the enzymic structure of thebiological materials is responsible for catalyzing thehydrolytic degradation of clear-coat at neutral pH.So, the biological degradation may be regarded as anenzymically induced hydrolytic cleavage [35].

In polyester/melamine coatings, the effect of thestructure of the polyester on the stability was studied.Polyesters with different acid monomers were used,isophthalic acid hexahydrophthalic anhydride, tereph-thalic acid phthalic anhydride, and 1,4 cyclohexanedi-carboxylic acid. It turned out that the most importantfactor in degradation is the high number of hydro-gen atoms attached to tertiary and secondary carbonsin the polymer structure. These are very sensitive toabstraction, which in turn favors photooxidation reac-tions [36].

Melamine resin coatings are often used for particle-boards. In certain environments such as hospitals andkitchens, high hygienic requirements are desirableand there is a need for improving their antimicrobialproperties. These aspects have been reviewed [37].

Alkyd/melamine resin compositions are mainlyused in industrial baking enamels. In a study, opti-mal coating properties could be achieved with analkyd/melamine resin ratio of 80/20, a curing tem-perature of 150 ◦C and a curing time of 20 min [38].

Alkyd resins with high hydroxyl numbers havebeen synthesized that are based on ricinoleic acidand phthalic anhydride as acid components. Glyc-erin, trimethylol propane, and ethoxylated pentaery-thritol serve as alcohol components. The alkyd resinswere used for baking enamels. The curing behavior ofalkyd/melamine resins was monitored by differential


scanning calorimetry (DSC). From these data theenthalpy of curing was calculated. The results of char-acterization suggest that the combinations of alkydresins using ricinoleic acid with melamine resins canbe used for the preparation of baking enamels [39].

Similarly, the curing behavior of alkyd/melamineresins based on dehydrated castor oil and soybeanoil with melamine resin has been investigated. Thekinetic parameters obtained by the transformation ofdynamic DSC results into isothermal data using theOzawa equation are in good agreement with thoseobtained directly by isothermal DSC. The apparentdegree of curing has a pronounced effect on the hard-ness of the resultant coating film [40].

6.6.2 Encapsulated DyesMelamine resin microcapsules that contain CI Dis-perse Blue 56 have been prepared by an in situ poly-merization technique [41]. The microcapsules can beused for dyeing behavior of nylon 6.6. The microen-capsulated dye exhibits good build-up, levelness, andfastness. It has been demonstrated that a microencap-sulated disperse dye can be used to replace conven-tional disperse dyes without dyeing additives, and theresulting effluent can be more easily recycled afterfiltration.

6.6.3 Porous ResinsThe polycondensation of a water-soluble melamine/formaldehyde composition under acidic conditionswithin a bicontinuous microemulsion comprising anoil phase, a water phase, and a surfactant yields gelswith large spherical voids [42]. Actually, the intrinsicnanoscopic feature size of the microemulsions can beused as a structural template. However, by the usage ofhydrophobic monomers such as benzoguanamine andcaprinoguanamine, a gel with aggregated nanoparti-cles is formed. Hydrophobic monomers diminish thephase separation. Porosities of 86% by volume areachieved with pore sizes of 65 nm.

Mesoporous melamine resins have been preparedfrom hexamethoxymethyl melamine as monomer anda block copolymer, i.e., Pluronic® F127 as the tem-plate [43].

In acidic conditions, hexamethoxymethylmelamine starts curing. In this way, the mesophasesformed by the template are replicated. Eventually,the template is removed by solvent extraction and amesoporous melamine resin is formed.

Materials with a surface area of up to 258 m2 g−1

and pore sizes of 7.8 nm are formed. At a ratio of1:1 of template to monomer an ordered mesoporousmelamine resin with a 2D hexagonal arrangement ofcylindrical pores is formed [43].

Mesoporous and microporous melamine resins canbe also synthesized by a templating method usingsilica nanoparticles [44]. The porous structure wascharacterized by X-ray scattering, gas sorption meth-ods, and electron microscopy. The porosity was alsoproven by the measurement of the sorption of carbondioxide. Porosities up to 61% and surface areas up to250 m2 g−1 can be achieved.

6.6.4 Resins with IncreasedElasticity

In foams and fibers, with increased elasticity, themelamine is partly replaced by a hydroxyalkyl sub-stituted melamine. To prepare these resins, melamineand substituted melamine are polycondensed togetherwith formaldehyde. The feed may also contain smallamounts of customary additives, such as disulfite, for-mate, citrate, phosphate, polyphosphate, urea, dicyan-diamide, or cyanamide [4]. Moldings are produced bycuring the resins in a conventional manner by addingsmall amounts of acids, preferably formic acid. Foamscan be produced by foaming an aqueous solutionor dispersion containing the melamine/formaldehydeprecondensate, an emulsifier, a blowing agent, and acuring agent.

6.6.5 MicrospheresMonodisperse melamine/formaldehyde microsphereshave been prepared via a dispersed polycondensationtechnique. The nucleation and growth of the parti-cles were achieved within short periods. A continu-ous coagulation occurred even in the presence of sur-factants [45]. Microcapsules are interesting becauseof the controlled-release properties of the respec-tive encapsulated substances. A fragrant oil can bemicroencapsulated by an in situ polymerization [46].The particle sizes ranged from 12 to 15 µm. The effi-ciency of encapsulation of the fragrant oil reached upto 67–81%.

Microcapsules were prepared in a capillaryflow microreactor and in a batch experiment. Themicrocapsules obtained from the microreactorshowed smaller particle diameters and a narrower


particle size distribution than those obtained in a batchexperiment [47].

References

[1] M. Higuchi, Melamine resins (overview), in:J.C. Salamone (Ed.), The Polymeric Materi-als Encyclopaedia: Synthesis, Properties andApplications, CRC Press, Boca Raton, FL,1999, pp. 837–838.

[2] Gesellschaft für Chemische Industrie in Basel,Verfahren zur Herstellung von 2.4.6-Triamino-1.3.5-triazin (Melamin), CH Patent 189 406,assigned to Ciba AG, February 28, 1937.

[3] G.M. Crews, S. Ji, C.U. Pittman Jr., R. Ran,Ammeline-melamine-formaldehyde resins(AMFR) and method of preparation, USPatent 5 254 665, Assigned to MelamineChemicals, Inc., Donaldsonville, LA, October19, 1993.

[4] J. Weiser, W. Reuther, G. Turznik, W. Fath,H. Berbner, O. Graalmann, Melamine resinmoldings having increased elasticity, US Patent5 162 487, Assigned to BASF Aktienge-sellschaft, Ludwigshafen, DE, November 10,1992.

[5] F.C. Dupre, M.E. Foucht, W.P. Freese,K.D. Gabrielson, B.D. Gapud, W.H. Ingram,T.M. McVay, R.A. Rediger, K.A. Shoe-make, K.K. Tutin, J.T. Wright, Cyclic urea-formaldehyde prepolymer for use in phenol-formaldehyde and melamine-formaldehyderesin-based binders, US Patent 6 379 814,Assigned to Georgia-Pacific Resins, Inc.,Atlanta, GA, April 30, 2002.

[6] R.C. Dante, J.M. Gil, L. Pallavidino, F.Geobaldo, Synthesis under pressure of poten-tial precursors of CNx materials based onmelamine and phenolic resins, J. Macromol.Sci. B. 49 (2) (2010) 371–382.

[7] R.C. Dante, D.A. Santamaria, J.M. Gil,Crosslinking and thermal stability of ther-mosets based on novolak and melamine, J.Appl. Polym. Sci. 114 (6) (2009) 4059–4065.

[8] R.A. Khan, M.A. Khan, N. Sharmin, A. Rah-man, S. Nahar, B. Sarker, K. Dey, H.U.Zaman, Z.H. Bhuiyan, M.Z.I. Mollah, Fabri-cation and mechanical characterization of jute

fiber-reinforced melamine matrix composite,Polym-Plast. Technol. 50 (2) (2011) 147–152.

[9] F. Wu, Flame retardant epoxy resins contain-ing microcapsules, Adv. Mater Res. (Zurich,Switzerland) 197–198 (2) (2011) 1346–1349.

[10] Y.L. Lam, C.W. Kan, C.W.M. Yuen, Flame-retardant finishing in cotton fabrics using zincoxide co-catalyst, J. Appl. Polym. Sci. 121 (1)(2011) 612–621.

[11] Y.L. Lam, C.W. Kan, C.W.M. Yuen, Effectof zinc oxide on flame retardant finishingof plasma pre-treated cotton fabric, Cellulose(Dordrecht, Netherlands) 18 (1) (2011) 151–165.

[12] Y.L. Lam, C.W. Kan, C.W. Yuen, Effect ofoxygen plasma pretreatment and titanium diox-ide overlay coating on flame retardant finishedcotton fabrics, BioResources 6 (2) (2011)1454–1474.

[13] M. Gao, H. Li, W. Feng, Flame retardanceand thermal degradation of intumescent flameretardant polypropylene with microencapsu-lated TPMP, Combust. Sci. Technol. 182 (10)(2010) 1446–1456.

[14] M. Gao, Y. Yan, Thermal degradation and flameretardancy of epoxy resins containing microen-capsulated flame retardant, PMSE Preprints 98(2008) 533–535.

[15] N. Ayrilmis, Enhancement of dimensional sta-bility and mechanical properties of light MDFby adding melamine resin impregnated paperwaste, Int. J. Adhes. Adhesives 33 (2012)45–49.

[16] T. Ikeda, T. Sugimoto, M. Nojiri, K. Magara,S. Hosoya, K. Shimada, Alkali pretreatmentfor producing bioethanol fuel from ligno-cellulosics, Part 2: Bioethanol productionfrom waste and recycled materials, Kami PaGikyoshi 63 (5) (2009) 581–591.

[17] Y. Tian, L. Chen, L. Gao, J. Michel, C.Frederick, C. Wan, Y. Li, W.A. Dick, Compost-ing of waste paint sludge containing melamineresin as affected by nutrients and gypsum addi-tion and microbial inoculation, Environ. Pol-lut. (Oxford, United Kingdom) 162 (2012)129–137.

[18] R. Monteiro de Barros Filho, L.M. Mendes,K.M. Novack, L.O. Aprelini, V.R. Botaro,Hybrid chipboard panels based on sugarcanebagasse, urea formaldehyde and melamine


formaldehyde resin, Ind. Crop. Prod. 33 (2)(2011) 369–373.

[19] P. Girods, A. Dufour, Y. Rogaume, C.Rogaume, A. Zoulalian, Pyrolysis of woodwaste containing urea-formaldehyde andmelamine-formaldehyde resins, J. Anal. Appl.Pyrol. 81 (1) (2008) 113–120.

[20] P. Girods, A. Dufour, Y. Rogaume, C.Rogaume, A. Zoulalian, Thermal removal ofnitrogen species from wood waste containingurea formaldehyde and melamine formalde-hyde resins, J. Hazard. Mater. 159 (2–3) (2008)210–221.

[21] S. Tohmura, A. Inoue, S.H. Sahari, Influenceof the melamine content in melamine-urea-formaldehyde resins on formaldehyde emis-sion and cured resin structure, J. Wood Sci. 47(6) (2001) 451–457.

[22] L.H. Su, S.R. Qiao, J. Xiao, X. Tang, G.D.Zhao, S.W. Fu, Synthesis and propertiesof high-performance and good water-solublemelamine-formaldehyde resin, J. Appl. Polym.Sci. 81 (13) (2001) 3268–3271.

[23] B.-D. Park, S.-M. Lee, J.-K. Roh, Effects offormaldehyde/urea mole ratio and melaminecontent on the hydrolytic stability of curedurea-melamine-formaldehyde resin, Eur. J.Wood Wood Prod. 67 (1) (2009) 121–123.

[24] W. Gindl, F. Zargar-Yaghubi, R. Wim-mer, Impregnation of softwood cell wallswith melamine-formaldehyde resin, Bioresour.Technol. 87 (3) (2003) 325–330.

[25] Y. Chai, J. Liu, Z. Xing, Dimensional sta-bility, mechanical properties and fire resis-tance of MUF-boron treated wood, Adv. Mater.Res. (Durnten-Zurich, Switzerland) 341–342(1) (2012) 80–84.

[26] X. Liu, J. Zhang, Y. Yang, S. Zhang, J. Li,Effect of melamine content in MUF resin onthe durable properties of plywood, Appl. Mech.Mater. 71–78 (5) (2011) 3160–3164.

[27] S.R. Shukla, D.P. Kamdem, Swelling ofpolyvinyl alcohol, melamine and urethanetreated southern pine wood, Eur. J. Wood WoodProd. 68 (2) (2010) 161–165.

[28] U. Mller, M. Steiner, Colour stabilisation ofwood composites using polyethylene glycoland melamine resin, Eur. J. Wood Wood Prod.68 (4) (2010) 435–443.

[29] F.A. Ozdemir, B. Demirata, R. Apak, Adsorp-tive removal of methylene blue from sim-ulated dyeing wastewater with melamine-formaldehyde-urea resin, J. Appl. Polym. Sci.112 (6) (2009) 3442–3448.

[30] M.A. Abd, El-Ghaffar, Z.H. Abdel-Wahab,K.Z. Elwakeel, Extraction and separation stud-ies of silver(I) and copper(II) from theiraqueous solution using chemically modifiedmelamine resins, Hydrometallurgy 96 (1–2)(2009) 27–34.

[31] G. Nishino, H. Sugimoto, E. Nakanishi, Prepa-ration and properties of acrylic melamine hardcoating, J. Appl. Polym. Sci. 123 (1) (2012)307–315.

[32] Z. Ranjbar, A. Jannesari, S. Rastegar, S.Montazeri, Study of the influence of nano-silica particles on the curing reactions ofacrylic-melamine clear-coats, Prog. Org. Coat.66 (4) (2009) 372–376.

[33] R. Han, Y. Zhang, Studies on performance ofcured water-borne melamine-acrylic emulsioncoatings, J. Adhes. Sci. Technol. 25 (8) (2011)883–892.

[34] B. Ramezanzadeh, M. Mohseni, H. Yari, Therole of basecoat pigmentation on the biologicalresistance of an automotive clearcoat, J. Coat.Technol. Res. 7 (6) (2010) 677–689.

[35] B. Ramezanzadeh, M. Mohseni, H. Yari, S.Sabbaghian, An evaluation of an automotiveclear coat performance exposed to bird drop-pings under different testing approaches, Prog.Org. Coat. 66 (2) (2009) 149–160.

[36] M.A.J. Batista, R.P. Moraes, J.C.S. Barbosa,P.C. Oliveira, A.M. Santos, Effect of thepolyester chemical structure on the stabilityof polyester-melamine coatings when exposedto accelerated weathering, Prog. Org. Coat. 71(3) (2011) 265–273.

[37] A. Kandelbauer, P. Widsten, Antibacterialmelamine resin surfaces for wood-based fur-niture and flooring, Prog. Org. Coat. 65 (3)(2009) 305–313.

[38] S.M. Cakic, L.B. Boskovic, FTIR analysis andthe effects of alkyd/melamine resin ratio onthe properties of the coatings, Hem. Ind. 63(6) (2009) 637–643.

[39] R. Radicevic, M. Jovicic, J. Budinski-Simendic, Preparation and curing of alkyd


based on ricinoleic acid/melamine coatings,Prog. Org. Coat. 71 (3) (2011) 256–264.

[40] M.C. Jovicic, R.Z. Radicevic, J.K. Budinski-Simendic, Curing of alkyd based on semi-drying oils with melamine resin, J. Therm.Anal. Calorim. 94 (1) (2008) 143–150.

[41] J.-L. Ji, S.-L. Chen, X.-J. Yang, L.-D. Lu,W. Xin, L.-M. Yang, The dyeing of nylonwith a microencapsulated disperse dye, Color.Technol. 123 (5) (2007) 333–338.

[42] C. du Fresne von Hohenesche, D.F. Schmidt,V. Schadler, Nanoporous melamine-formal-dehyde gels by microemulsion templat-ing, Chem. Mater. 20 (19) (2008) 6124–6129.

[43] K. Kailasam, Y.-S. Jun, P. Katekomol, J.D.Epping, W.H. Hong, A. Thomas, Mesoporousmelamine resins by soft templating of block-co-polymer mesophases, Chem. Mater. 22 (2)(2010) 428–434.

[44] A. Wilke, J. Weber, Hierarchical nanoporousmelamine resin sponges with tunable porosity-porosity analysis and CO2 sorption properties,J. Mater. Chem. 21 (14) (2011) 5226–5229.

[45] I.W. Cheong, J.S. Shin, J.H. Kim, S.J. Lee,Preparation of monodisperse melamine-formaldehyde microspheres via dispersedpolycondensation, Macromol. Res. 12 (2)(2004) 225–232.

[46] H.Y. Lee, S.J. Lee, I.W. Cheong, J.H. Kim,Microencapsulation of fragrant oil via in situpolymerization: Effects of pH and melamine-formaldehyde molar ratio, J. Microencapsul.19 (5) (2002) 559–569.

[47] T. Sawada, M. Korenori, K. Ito, Y. Kuwahara,H. Shosenji, Y. Taketomi, S. Park, Preparationof melamine resin micro/nanocapsules byusing a microreactor and telomeric surfac-tants, Macromol. Mater. Eng. 288 (12) (2003)920–924.

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Reactive Polymers Fundamentals and Applications || Melamine Resins