Pigment & Resin TechnologyPhysicochemical colourants effects on polymeric composites printing tonerZahra Bazrafshan Maryam Ataeefard Farahnaz Nourmohammadian

Article information:To cite this document:Zahra Bazrafshan Maryam Ataeefard Farahnaz Nourmohammadian , (2014),"Physicochemical colourants effects on polymericcomposites printing toner", Pigment & Resin Technology, Vol. 43 Iss 5 pp. 245 - 250Permanent link to this document:http://dx.doi.org/10.1108/PRT-09-2013-0085

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Physicochemical colourants effects onpolymeric composites printing toner

Zahra BazrafshanDepartment of Printing Science and Technology, Institute for Color Science and Technology, Tehran, Iran

Maryam AtaeefardDepartment of Printing Science and Technology, Institute for Color Science and Technology, Tehran, Iran, and

Farahnaz NourmohammadianCenter of Excellence for Colour Science and Technology, and Department of Organic Colorants, Institute for Colour Science

and Technology, Tehran, Iran

AbstractPurpose – This paper aims to report on production of the colour digital printing toners cyan, magenta and yellow. Colour digital electrophotographicprinting is currently in high demand. The provision of a large colour gamut depends on appropriate selection of precise colourants to produce tonercapable of producing a thin layer on paper.Design/methodology/approach – Printing toners were synthesised by the emulsion aggregation method, and then evaluated for chemicalconstitution and effects of the colourant substituents.Findings – Results demonstrated that increasing the polarity of a pigment produced better dispersion and lower particle size with narrowerdistribution and even better colour reproduction. While, changing a pigment’s characteristics did not affect the toner shape or its thermal properties.Practical implications – The developed method provides a simple way to synthesise colour printing toner.Social implications – Emulsion aggregation toners provide less hazardous materials during printing.Originality/value – Evaluations of the influence of solid-state parameters and physicochemical properties of the pigments on printing tonercharacteristics were done for the first time.

Keywords Emulsions, Composites, Colourant, Laser jet printer, Electrophotography

Paper type Research paper

IntroductionToner is a pigmented polymer composite used inelectrophotographic printing. In the past two decades,electrophotography has developed to the point where it is nowa legitimate alternative to other analogue print productiontechnologies such as offset lithography. According to themanufacturers’ revenue, electrophotography is the mostpopular digital printing technology in the world because itserves as the most commonly used printing technology foroffices (Kipphan, 2001).

The exact use of electrophotography can vary from onemanufacturer to another, but the basic principle remains thesame. Initially, a photoconductive belt or roller is uniformlycharged. Next, the image area is selectively discharged, usuallyby a laser. Then, polymeric toner is brought into contact withthe photoreceptor. Upon contact with the photoreceptor,toner particles attach to the discharged image areas of thephotoreceptor. This toner image is then transferred to the

substrate, where it is bonded using heat and pressure. Finally,the photoreceptor is cleaned of residual charge and toner inpreparation for reproduction of the next image (Figure 1)(Ohta and Rosen, 2006; Kumar et al., 2004).

Traditionally, polymeric toner was manufactured from acombination of polymer, pigment and additives. The resultingmass was extruded and mechanically ground to produce tonerparticles small enough for use in electrophotography(Hasegawa et al., 1999). Good results have been achieved bythis process, in which toner particles of more than 10 � in sizewere produced. However, one limitation of this method is thatof particle size; mechanical milling limits the minimumparticle size and consequently determines the limit toresolution and sharpness that is achievable. In addition tolimited mean particle size, mechanically milled toners exhibita wide distribution of particle size and shape, which has anadverse effect on image quality (Marshall, 1997).

One solution to these problems is application of chemicallyprepared toner (CPT). CPTs have smaller particle size, as wellas a uniform mean particle size distribution. Furthermore,CPT allows a device to deposit a thinner layer of toner ontothe substrate (Hasegawa et al., 1999; Marshall, 1997). Athinner toner requires less fusing of energy, which in turnfacilitates faster printing speed with reduced substratedistortion (Galliford, 2005a, 2005b). CPT is synthesised fromnanometre-sized particles by one of the following chemicalprocesses: suspension polymerisation, chemical milling oremulsion aggregation (EA) (Galliford, 2005a, 2005b;

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Pigment & Resin Technology43/5 (2014) 245–250© Emerald Group Publishing Limited [ISSN 0369-9420][DOI 10.1108/PRT-09-2013-0085]

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Ataeefard, 2013). Among chemical production processes fortoner, the technique of EA results in a more easily controlledtoner particle, especially in relation to having tight control overmorphology, particle size and particle size distribution that arerequired for optimum image quality (Ataeefard, 2013;Galliford, 2005a, 2005b).

Until recently, only black toners were availablecommercially, but in recent years, colour toners have alsobeen made available and are becoming more important.Coloured documents are increasingly being used in officesbecause they are visually attractive and have the ability tocommunicate a rich volume of information. Therefore, thereis an increasing demand for colourants suitable for colouredtoner printing (Freeman and Sokolowska, 1999; Hayami et al.,2008). Colour printing toner is achieved by sequential butseparate applications of the three primary subtractive (cyan,magenta, yellow [CMY]) colours plus black to the receiver(Ohta and Rosen, 2006). Colourants must satisfy colouristicrequirements such as hue, tinctorial strength andtransparency; furthermore, they must possess good heatresistance and be light fast; pigments should also meetturboelectric requirements (Baur and Macholdt, 1995).

Toners contain either pigments or dye as colourant. Oneadvantage of using pigments is that they do not readily diffuseduring the fusing step, as do dyes. Dye-based toner oftenresults in prints with better colour rendition thanpigment-based toner. Therefore, pigments with better colourefficiency should be selected to benefit from the advantages ofusing pigment as the colourant in toner production (Freemanand Sokolowska, 1999). Historically, the yellow pigmentsused in coloured toners have been diarylides or theirmonoarylide counterparts. Magenta pigments are normally ofquinacridones and the cyan pigments are copperphthalocyanines (Hayami et al., 2008).

There have been relatively few research works in recentyears on the development of colour toner. Baur and Macholdt(1995) reported on a new yellow type of pigment of thebenzimidazolone class that combines all aspects needed forcolour electrophotography (Macholdt, 1997). Baur andMacholdt (1995) introduced two red organic pigments andattempted to name the colourant that can be used in tonerproduction (Baur et al., 1993). In another work, Macholdtand Alexander (1988) investigated the influence of organic

pigment on the electrostatic chargeability of xerographictoners (Macholdt and Alexander., 1988).

For the first time, the intention of this study was to chooseappropriate pigments and investigate ways in which thephysicochemical, chemical constitution and solid-stateparameters of organic pigments are responsible for colourreproduction and physical characteristics of printing tonersynthesis produced by the EA method.

Experimental

MaterialsThe polymer used in this study was a styrene-acrylic resin(NS88; Simab Resin Co., Tehran, Iran) with a medium pHvalue and glass transition temperature (Tg) of 51.12°C. Apolyethylene emulsion wax (EE 95, Kala Kar Co., Tehran,Iran) was also used. Polyaluminium chloride was used as acoagulation agent.

Pigments used in this study were C.I. Pigment blue 15:3(P.B15:3) as the cyan colourant (BASF, Germany), C.I.Pigment Yellow 151 (P.Y:151) as the yellow colourant(Clariant, Switzerland) and C.I. Pigment Red 57:1 (P.R:57:1)and C.I. Pigment Red 122 (P.R:122) as the magentacolourant (Clariant, Switzerland). Scheme 1 illustratesstructure of the pigments. All pigments were used withpurification.

Method for preparation of printing tonerAll toners in this study were prepared using the sameprocedure (Ataeefard, 2013; Kmiecik-Lawrynowicz, 2003;Matsumura et al., 2001). In step A, a 1-L beaker was filledwith 24.5 g styrene-acrylic latex (particle size: 220 nm),0.2-1.5 g pigments, 3 g wax and 120 ml deionised water, andthe contents were mixed manually at room temperature for 15min. In step B, the contents were mixed using a homogeniserfor 5 min at the agitation speed of 5,000 rpm. The mixture wascontinuously mixed for 60 min at room temperature in step Cand a solution of 0.6 g coagulation agent in nitric acid wasadded drop-wise over 10 min until the pH value of the mixturereached 2. A gel was formed during this process that changedthe viscosity of the suspension from a Newtonian water-like

Scheme 1 The pigments’ molecular structures

N

N

N

NNN

N

N Cu

C.I. Pigment Blue 15:3 (P.B15:3)

N N

COO-OHSO3-

CH3 Ca2+

C.I. Pigment Red 57:1 (P.R:57:1)

O

OH

NN

O

O

NH

NH

NH

O

C.I. Pigment Yellow 151 (P.Y:151)

N

N

H

H

O

O

CH3

CH3

C.I. Pigment Red 122 (P.R:122)

Figure 1 Principle of electrophotographic printing process

Physicochemical colourants

Zahra Bazrafshan, Maryam Ataeefard and Farahnaz Nourmohammadian

Pigment & Resin Technology

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fluid to a shear thinning paste-like gel. In step D, temperatureof the mixture was increased to 50°C for about 60 min whilethe gel was continually mixed. The mixture was held at thistemperature for another 60 min in step E. In step F, thetemperature of the mixture was increased to 96°C for 60 minand, in step G, it was held at this temperature for a further 60min. The mixture was neutralised with sodium hydroxidesolution after the temperature had increased. Finally, themixture was cooled to 25°C, after which the produced microparticles were isolated from the water, washed to removedivalent ions, filtered and dried with a frizzed dryer (Figure 2).All mixing was done at the agitation speed of 1,250 rpm.

Based on the above procedure, some sets of experimentswere undertaken with different amounts of pigment (1.5 g ofP.B:15:3 for cyan toner termed C, 0.5 g of Y.P:151 for yellowtoner termed Y and 0.2 g of P.R:122 and 0.7 g of P.R:57:1 formagenta toner termed M) to explore the effects ofphysicochemical, chemical constitution and solid-stateparameters of organic pigments on physical characteristics ofcolour toner.

Characterisation of pigments and printing tonerPigment characteristicsThe pigments were characterised according to thephysicochemical and solid-state parameters; evaluations areshown in Table I.

Particle size measurementThe resultant colour toners were centrifuged and dispersed inwater followed by sonication for about 2 min to break down

aggregations. The dispersions were prepared for particle sizeand particle size distribution measurements that were taken ona particle size analyser (PSA, Malvern Rasterizer 2000,England) in the range of 0.02-2000 m. Evaluation of particlesize distribution was made using the span parameter:

Span � �D90�D10�/D50 (1)

where D50 represents diameter (�m) at which distributionsize is 50 per cent above and 50 per cent below.

Scanning electron microscopic analysisMorphology of the pigmented composite toners was observedby scanning electron microscopy (SEM, KYKY-EM3200,China), and determinations for circularity of the toners weremade by image J software. Prior to imaging, toner powderswere coated with Au to make them conductive.

Measurement of glass transition pointThermal behaviour of the toner was conducted on adifferential scanning calorimeter (DSC, PerkinElmer USA).Approximately 5 mg of each sample was loaded on to a panand sealed with a covering lid. Measurements were taken overa temperature range of 0-150°C at a heating rate of 10°C/minin an atmosphere of nitrogen.

Spectrophotometric analysisColour measurement of the samples was taken using a SP64spectrophotometer (Greta Macbeth, USA). Determinationswere made for spectral reflectance factor samples and thentransformed into CIELAB colorimetric coordinates (L�, a�,b�) using CIE standard illuminant D65 and a CIE 1964standard colorimetric observer. Total changes in colour(�ELab) were calculated for each sample using the CIE�E2000

colour difference equation (ICC Specification version 4.2.0.0,2004).

An increase in L� indicates lightening of a sample. A positive�a� signifies a colour shift towards red; a negative �a� signifiesa colour shift towards green. Similarly, a positive �b� signifiesa colour shift towards yellow; a negative �b� signifies a colourshift towards blue.

The resultant colour toners were printed in a controlledenvironment (23°C, 50 per cent relative humidity) using amonochrome laser-jet printer (HP 1100, laser-jet printer).This printer changed to only have a hot roll fusing systemcontaining two metal rolls covered with silicone rubber andheated from inside the rolls.

Result and discussion

Influence of physicochemical and solid-stateparametersAs stated before, organic pigments are the most widely usedcolourant in electrophotographic printing because of easytoner production and good printing quality. From the widevariety of available pigments, only four characteristic types arediscussed here in detail as colourants for producing colourprinting toner, namely, C.I. P.B15:3: copper (2�)phthalocyanine-29, 31-diide; C.I. P.R:57:1: 2-naphthalenecarboxylic acid, 3-hydroxy-4-[(4-methyl-2-sulfophenyl) ado] – calcium salt; C.I. P.Y:151: benzoic acid,2-[[1-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-oxopropyl]azo]; and C.I. P.R:122: quino [2, 3-b]

Figure 2 The variation of pH and temperature during the synthesisprocess of the toner composites

Table I Physicochemical characteristics of pigments

NameConductivity

(us/cm)

Heatresistance

(°C) pH

Specificsurface

area (m2/g)Density(g/cm3)

P.B. 15:3 200 300 5.5-8.5 57 1.54P.Y. 151 500 200 6-7 23 1.55P.R. 57:1 500 170 7-8 83.3 1.7P.R. 122 500 300 7-8 63 1.45

Physicochemical colourants

Zahra Bazrafshan, Maryam Ataeefard and Farahnaz Nourmohammadian

Pigment & Resin Technology

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acridine-7, 14-dione (Scheme 1). Appropriate colourmatching was done with the following toners of OriginalEquipment Manufacturer (OEM): 1.5 g P.B. 15:3 for the cyantoner, 0.5 g P.Y. 151 for the yellow toner and a mixture of 0.7g of P.R.57:1 and 0.2 g of P.R.122 for the magenta toner.Physicochemical and solid-state parameters of these pigmentscan be modified either by special finishing procedures or byvariation in the conditions for synthesis. Variations of thesolid-state parameters in these pigments give rise to change intoner particle size and particle size distribution; these areshown in Table II (Blaszak et al., 2000; Hayami et al., 2008;Shamekhi and Nourmohammadian, 2013).

In terms of pigments tested in this study, the lowestpolarity was determined in P.B. 15:3 and then P.R. 122with symmetric molecular structure. However, P.Y. 151and P.R. 57:1 having several polar functional groups weredetermined as polar molecules with better wettability due tointermolecular hydrogen bond ability. Therefore, P.Y. 151demonstrated the best dispersion and compatibility andP.B. 15:3 demonstrated the worst dispersion in terms ofpolar toner production medium (acrylic resin). Thus yellowtoner has smaller particle size than does the magenta tonerand the blue toner (Table II). In the case of magenta toner,a combination of polar P.R. 57:1 and non-polar P.R. 122made the mixer mid-polar, which resulted in mediumparticle size, while particle size distribution was broader incomparison with the yellow and blue toners. However,comparisons of toner particle sizes showed that polarsubstitutions on the pigments with intermolecular hydrogenbonding had a better ability to lower the toner particle sizeand narrow particle size distribution owing to a bettersolvatochromic effect in an aqueous medium. Of course, inaddition to pigment polarity, compatibility and dispersion,other physicochemical and solid-state properties such asparticle size also had an effect on toner particle size andparticle size distribution.

Figure 3 shows toner surfaces as depicted by electronmicrographs. A powder toner particle is approximately 6-14 �in diameter, as confirmed by results for particle size.Circularity values of the toner particles prepared with thevarious pigments were calculated using image J software.Results shown on Table II determine that variation in apigment’s physicochemical and solid-state parameters do notaffect the circularity of a colour toner, and all coloured tonershave a semi-spherical or a potato shape (circularityapproximately 0.8).

SEM images of colour toner particles show that particleshad a rough surface. This phenomenon can be attributed tothe particular surface tensions of the toner’s constituents thatresulted in migration of the pigment from the inner part of theparticle to its surface. Therefore, as the compatibility of polaryellow pigment with the toner production medium was high,the amount of pigment migration to the surface was low andthe toner surface was less rough, while incidence of migrationand surface roughness were significant in the blue toner(Matsumura et al., 2002).

Colour and thermal characteristicsSpectrophotometric characteristics of the colour toner (C, Mand Y) and OEM toners (RC, RM and RY) are presented inTable III. It is noteworthy that for colour management in anoffice, it is desirable to achieve colour fidelity regardless of theparticular device that is used. Requirements for colour fidelityare variable according to the type of image being reproduced.Examples show that the colour tolerance range of skin colourfor natural images in electrophotographic digital printing isCIE�E2000 � 5. As expected, despite some small changes,colour variations were determined as acceptable and were ingood agreement with the reference toner (Ohta and Rosen,2006).

Results demonstrated that even evaluations for colorimetricbehaviour exhibited a strong dependence on dispersionquality. Better pigment dispersion in toner resins causedbetter agreement with OEM toner and a lower �E value. As,the yellow toner with its polar nature and better dispersion andcompatibility showed a lower �E value and had better colourreproduction.

In the fusing process, polymeric toner is heated to its Tg. AtTg, solid toner changes to a liquid state and individual particlesbegin to coalesce. Above Tg, toner viscosity decreases rapidly.As liquefaction occurs, the toner penetrates and bonds to the

Table II The particle size, particle size distribution, shape factor andthermal characteristics of the synthesised toners

SampleParticle

size (�m) spanSofteningpoint (°C) Tg (°C) Circularity

Cyan 11.36 1.21 138 62.31 0.880Magenta 9.69 1.90 135 71.65 0.854Yellow 5.40 1.18 131 59.03 0.833

Figure 3 SEM micrographs of colour printing toner particles

Physicochemical colourants

Zahra Bazrafshan, Maryam Ataeefard and Farahnaz Nourmohammadian

Pigment & Resin Technology

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substrate fibres. The resin’s Tg should be high enough forstorage and the melting point Tm should be as low as possibleto conserve energy. Normally, Tg is about 50–70°C(Einarsson, 2002; Ichimura, 1987).

The results of DSC analyses of toners with the softeningpoints of toners are depicted in Figure 4 and Table II,respectively. Figure 4 shows the Tg of the toners C, M and Yas 62.31, 71.65 and 59.03°C, respectively. Similarly, thesoftening point evaluations for the toners C, M and Y were138, 135 and 131°C, respectively. This temperature can berelated to the Tg of a polymer component (styrene-acrylicresin) used in toner formulation. Based on the results of DSC,it seems that all toners have appropriate thermalcharacteristics for laser printing. Variation in terms ofphysicochemical and solid-state parameters of a pigment doesnot affect a toner’s thermal properties. Figure 5 shows printedsamples of colour toners. The printed samples showuniformity.

ConclusionDigital printing is making a big impact on the printingindustries; therefore, production optimisation is a focus ofdiscussion. The aim of this work is to produce colour toners(cyan, magenta and yellow) and investigate the effect ofcolourant in final toner’s properties. Results have shown thatorganic pigment physicochemical constitution and solid-stateproperties can have a marked influence on particle size,particle size distribution and colour reproduction of a colourprinting toner. In this study, three different pigments, namely,C.I. P.B15:3: copper (2�) phthalocyanine-29, 31-diide,C.I. P.R:57:1: 2-naphthalenecarboxylic acid, 3-hydroxy-4-[(4-methyl-2-sulfophenyl) azo] – calcium salt, C.I. P.Y:151:benzoic acid, 2-[[1-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-oxopropyl]azo] and C.I. P.R:122:quino [2, 3-b] acridine-7, 14-dione, with various differentphysicochemical and solid-state properties were used toprepare colour printing toner using the EA method. Resultsshow that yellow pigment had higher polarity, bettercompatibility and dispersion and produced toner with smallerparticle size and particle size distribution compared to the bluenon-polar pigment (particle size: 5.40 and 11.36,respectively). However, shape of the colour toner did notchange with a pigment’s physicochemical and solid-stateproperties (circularity approximately 0.880). Colourreproduction affects pigment characteristics indirectly.Better colour reproduction was determined with the yellowtoner because of its higher polarity, more compatibility andbetter dispersion (CIE�E2000: 1.19). All colour toners showappropriate thermal characteristics and fused in a uniformappearance.

References

Ataeefard, M. (2013), “Production of carbon black acryliccomposite as an electrophotographic toner via emulsionaggregation method: investigation the effect of agitationrate”, Journal of composite part B: Engineering, Vol. 64,August, pp. 78-83.

Baur, R. and Macholdt, H.T. (1995), “Organic pigments fordigital color printing”, IS&T’s NIP11, pp. 118-121.

Baur, R., Macholdt, H.T. and Hoechst, A.G. (1993),“Charge control agents for triboelectric (friction) charging”,Journal of Electrostatics, Vol. 30, pp. 213-222.

Blaszak, S.E., Dalal, E.N., Natale-hoffman, K.M.,Eknuld, E.A. and Julien, A.P.C. (2000), “Colour tonercompositions and processes thereof”, Us Patent, No.6066422.

Einarsson, F. (2002), “Thermal analysis of toners”, AnnualTransactions of the Nordic Rheology Society, Vol. 10,pp. 155-157.

Freeman, H. and Sokolowska, J. (1999), “Developments indyestuff chemistry”, Review Progress Coloration, Vol. 29No. 1, pp. 8-22.

Galliford, G. (2005a), Chemically Prepared Toners – A Study onMarkets and Technologies, Galliford Consulting &Marketing, Ventura, CA.

Galliford, G. (2005b), Particle Shape of Toners and TheAdvantage of Using Chemical Toner Manufacturing Methods,Galliford Consulting & Marketing, Ventura, CA.

Table III The colorimetric properties of the synthesised and referencetoners

Sample L� a� b� �E2000

Cyan 55.7 �14.10 �26.80 3.84RC 52.07 �14.86 �30.80Magenta 53.85 40.72 6.94 3.05RM 51.31 45.75 6.64Yellow 85.15 3.84 83.54 1.19RY 85.79 3.46 78.38

Figure 4 DSC diagram of the colour printing toners

Figure 5 Photograph of colour toners printed onto paper with HP1100 laser-jet printer

Physicochemical colourants

Zahra Bazrafshan, Maryam Ataeefard and Farahnaz Nourmohammadian

Pigment & Resin Technology

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Hasegawa, J., Yanagida, N. and Tamura, M. (1999), “Tonerprepared by the direct polymerization method incomparison with the pulverization method”, Colloids andSurfaces A: Physicochemical Engineering Aspects, Vol. 153No. 1, pp. 215-220.

Hayami, K., Tanikawa, H., Ida, T., Hashimoto, A.,Komatsu, N. and Fujikawa, H. (2008), “Colour toner”, USPatent No. 7452647B2.

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Kipphan, H. (2001), Handbook of Print Media: Technologiesand Production Method, Springer, New York, NY,pp. 689-698.

Kmiecik-Lawrynowicz, G., (2003), “New EA toners for highquality digital color printing”, International Conference onDigital Production Printing and Industrial Application, Vol. 2No. 1, Barcelona, May, pp. 211-213.

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About the authors

Zahra Bazrafshan received her BSc in computer engineering(2003) at Azad University – south branch, Tehran, Iran. HerMSc in printing engineering was obtained at Institute forColor Science and Technology (Tehran, Iran) under thesupervision of Assistant Professor M. Ataeefard and AssociateProfessor F. Nourmohammadian in 2013. Her major field ofstudy includes synthesis of colour printing toner via emulsionaggregation method.

Maryam Ataeefard has a PhD in polymer engineering –color technology obtained at Amir Kabir University (TehranPolytechnic), Tehran, Iran. She is currently an AssistantProfessor in Printing Science and Technology, Institute forColor Science and Technology (ICST), Tehran, Iran. Herresearch interest work is focused on the electrophotographicdigital printing, i.e. printing toner composite and its synthesismethods, application and characteristics. Maryam Ataeefard isthe corresponding author and can be contacted at:ataeefard-m@icrc.ac.ir

Farahnaz Nourmohammadian has a PhD in organicchemistry obtained at Tarbiat Modarres University, Tehran,Iran. She is currently an Associate Professor at the OrganicColorant Department, Institute for Color Science andTechnology (ICST), Tehran, Iran, and a member of Center ofExcellence for Color Science and Technology. Her researchinterest work is focused on the synthesis of organiccompounds, i.e. organic colourants and intermediates,photochromic compounds and study on their applications.

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Physicochemical colourants

Zahra Bazrafshan, Maryam Ataeefard and Farahnaz Nourmohammadian

Pigment & Resin Technology

Volume 43 · Number 5 · 2014 · 245–250

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