RESEARCH • CHEMISTRY 49 77 Science

Indian Journal of Science • Analysis

Patel Jigar et al.Effect of domestic laundering on color fastness of three newly synthesized reactive dyes on 100 % cotton fabric,Indian Journal of Science, 2013, 4(11), 68-75, www.discovery.org.inhttp://www.discovery.org.in/ijs.htm © 2013 Discovery Publication. All Rights Reserved

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Patel Jigar R1, Patel Mitesh H2, Shrivastav Pranav S2, Sanyal Mallika3☼

1. Research Scholar, Chemistry Department, Kadi Sarva Vishwavidyalaya, Sarva Vidyalaya Campus, Sector 15/23, Gandhinagar- 382015, India2. Associate Professor, Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad- 380009, India3. Associate Professor, Department of Chemistry, St. Xavier’s College, Navrangpura, Ahmedabad- 380009, India

☼Corresponding author: Associate Professor, Department of Chemistry, St. Xavier’s College, Navrangpura, Ahmedabad 380009, India. Mail:[email protected], Mobile No: (+91)-9825972775

Received 07 July; accepted 24 August; published online 01 September; printed 16 September 2013

ABSTRACTThe article describes synthesis and colour fastness study of three reactive dyes, Reactive Red A, Reactive Red B and Reactive Red C on 100 % cottonfabric using domestic laundering. These reactive dyes contain chlorotriazine, sulfo vinylsulfone and sulfo tobiaz acid hetero functionality. The purity of thedyes was ascertained by UFLC analysis on BDS Hypersil C18 (250 × 4.6 mm, 5 µm) column using 1.5 mM tetra-butyl ammonium bromide in deionizedwater: acetonitrile (40: 60, v/v) as the mobile phase. The synthesized dyes contain several reactive sulphonic acid functionalities which markedly improveddyeing on cotton fiber. Different parameters like primary and secondary exhaustion, fixation ratio and fixation yield were calculated for the dyeing process.Fading of colour due to domestic laundry has been extensively studied using four commercially available detergents. Colour fastness was evaluated fordomestic washing, rubbing, perspiration and exposure to sunlight. The results indicate superior performance of dyed cotton fabric with the newlysynthesized dyes based on International Geometric Grey Scales measurements.

Keywords: Reactive red A; Reactive red B; Reactive red C; Sulfo vinylsulfone; Sulfo tobiaz acid; Cotton fiber; Colour fastness

Abbreviations: UFLC-ultra fast liquid chromatography; TLC-thin layer chromatography

To Cite This Article:Patel Jigar R, Patel Mitesh H, Shrivastav Pranav S, Sanyal Mallika. Effect of domestic laundering on color fastness of three newly synthesized reactivedyes on 100 % cotton fabric. Indian Journal of Science, 2013, 4(11), 68-75

1. INTRODUCTIONDyes are widely used in the field of leather, paper, printing inks, plastics, cosmetics, paints, pharmaceutical, food and textileindustries (Giwa et al., 2012). Amongst different classes of dyes, reactive dyes are the preferred choice of colorants toproduce colouring effect for several technical advantages. They are extensively used in the textile industry due to wide varietyof color shades, superior wet fastness profiles, simplicity of application and minimal energy consumption (Ojstrsek et al.,2008; Lee and Pavlostathis, 2004). Reactive dyes chemically react with the fiber to form a strong covalent connection thatgives rise to high performance to wet treatments such as laundering. They are the single largest range of dyes used fordyeing of cotton fibers and their blends (Fergusson, 2008). The characteristic features of water soluble reactive dyes includes

the chromophoric group, the reactive system, bridging group and one or moresolubilizing group. Chromophores which contribute to the colour mainly includeazo, anthraquinone, triphenodioxazine and copper phthalocyanine. The reactivesystem facilitates the dye to form a covalent bond with the hydroxy group incellulose; amino, hydroxyl or thiol groups in protein fibres and with the aminogroup in polyamide (Shore, 1995; Broadbent, 2001). The two most commonlyencountered reactive dyes have chlorotriazine, vinyl sulfone or chlorotriazine-vinyl sulfone heterobifunctional moieties (Mazumdar and Haque, 2001). The firstreactive dye for cotton was developed in 1955 and was based ondichlorotriazine groups (Finch, 1979). Dyeing with this dye under alkalineconditions gave excellent wet fastness. The general reaction between thereactive dye and the cellulose fibre can be represented as (Srivastva, 2003),

Dye-R (reactive dye) + Cell-OH (cellulose fibre) → Dye-O-Cell + RH

where R is the reactive part of the dye. Further, it is well understood thatincreasing the number of reactive groups attached to the dye moleculeincreases fixation yields, good solubility and fastness properties. Reactive dyes

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Effect of domestic laundering on color fastness of three newlysynthesized reactive dyes on 100 % cotton fabric

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Comparison:The present study with synthesized reactive dyes has shown excellentfastness properties on 100 % cotton fabric. Due to more number ofsulphonic acid groups, the dye application process required very lowliquor ratio compared to commercial dying on cotton fabric.

Content:Reactive dyes are unique as they contain specific chemical groupswhich are capable of forming covalent linkage with the textilesubstrate. However, the ultimate success of dyeing cotton fabric withreactive dyes depends on the number of reactive groups, theirchemical nature, molecular mass, number of sulphonic acid groups,ratio of sulphonic acid groups to aromatic carbons (hydrophobic –hydrophilic balance), linear or planar shape of the dye molecule andthe presence of other functional groups. Further, pretreatment offabric is another crucial aspect in dyeing with reactive dyes.

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are applied to cotton fiber by a variety of processes like exhaust orbatch dyeing method, pad-batch, pad-steam, pad-bake, print-steam,and print-bake (Ikiz and Keskin, 2011).

Colour fastness to washing is the common quality parameter,which is essential especially for the consumer. Domestic and industriallaundry cleaning processes influence the fading of dyes from cottontextiles. The composition of laundry detergents vary widely with somecontaining more alkali, while others have higher amounts of oxygengenerating bleaching compounds such as sodium perborate or sodiumpercarbonate. Typical detergents contain apart from the activedetergent (alkyl benzene sulphonates), several other essentialconstituents like sodium carbonate, sodium sulphate, carboxymethylcellulose, sodium silicate, tri poly phosphate, foaming agent and opticalbrightners in trace amounts (Woodhouse, 1976). Fading of colour ismainly due to exposure to sunlight and also because of some chemicalreactions which occur during washing of fabric and garments. Limitedwork has been carried out on the effect of consecutive wet exposure,drying, then washing and wet exposing a number of times usingdomestic laundry detergents, which is a normal process in a householdsituation. To realise this, it is imperative to stimulate “real life” domesticwashing and drying process for practical purposes. Thus, the aim of thepresent work was twofold, (a) to study the effect of four domesticlaundry detergents and residual alkali remaining in the cotton fabric onthe colour fading properties of three reactive dyes (Red A, B and C), (b)to investigate the effect of repeated washing cycles, sunlight, wet anddry rubbing and perspiration on the dyed fabric during normalhousehold laundering.

2. EXPERMENTAL2.1. Chemicals and materialsReference reactive dyes, Reactive Red BS, Reactive Red M5BVS,

Reactive Red ME4BL of technical grade were obtained from JCL (Ahmedabad, India), H-acid (1-amino-8-hydroxynapthalene-3-6-disulfonic acid, 98 %) and sulfo vinylsulfone (4-(β-ethylsulphate) sulphonyl aniline, 99.2 %) were procured from MayurChemicals (Ahmedabad, India) and Atul Ltd. (Valsad, India) respectively. Sulfo tobiaz acid (2-naphthylamine-1,5-disulfonicacid, > 95 %) was obtained from Shree Hari Chemicals (Ankleshwar, India). Cyanuric chloride (2,4,6-trichloro-1,3,5-triazine,98.4 %) was purchased from IDI Ltd. (Ahmedabad, India). Sodium chloride, potassium chloride, sodium carbonate, sodiumhydroxide, hydrochloric acid, sodium lauryl benzene sulfonate, tri-sodium phosphate, ammonium perchlorate were ofcommercial grade. Analytical grade ethyl acetate and n-propanol solvents used for TLC were obtained from Merck SpecialtiesPvt. Ltd. (Mumbai, India). Four commercially available detergents sold under the brand name, Tide and Ariel from Procter &Gamble and Rin and Surf Excel from Hindustan Unilever Limited were procured from local market in Ahmedabad. Cottonfabrics (plain weave, 36's warp and 30's weft, yarn density 72/inch warp and 69/inch weft) were dried at about 100 0C for oversix hours after de-sizing with ammonium perchlorate, NaOH and sodium lauryl benzene sulfonate (Kanazawa et al., 1986).

2.2. Instrumentation and conditionsA digital lux meter from Sudershan Measuring & Engineering Pvt. Ltd., (New Delhi, India) was used to measure sunlightintensity. A digital EH1000 pH meter from Line Seiki (Japan) was used for pH measurements. UV absorption studies werecarried out on a Varian Cary 400 UV–Visible spectrophotometer (Palo Alto, CA, USA) with 10 mm matched quartz cells. ABeckman DK-2A double-beam spectrophotometer (Maryland, USA) equipped with an Ulbricht sphere and powered by ahydrogen lamp was used to measure UV transmittance through the fabric samples. The fabric samples were dyed in a SLI440 dyeing machine (dye bath) manufactured by Sahas Laboratory Instruments (Ahmedabad, India). Xenoster model (IS-2454-85) was used to test color fastness to light. Thermolab model (IS-687-79) was used to determine washing fastness ofdyed fabric. Perspirometer model Sashmira (IS‐971‐83) was used for the testing of perspiration fastness of dyed cotton, whileCrock meter from Ravindra Engineering (IS‐766‐88) was used for testing rubbing fastness of the dyed cotton. Thin layerchromatography was performed on pre-coated silica gel 60 F254 plates from E. Merck (Darmstadt, Germany). Purity wasdetermined on Shimadzu Prominence UFLC with SPD-20A detector using BDS Hypersil C18 (250 × 4.6 mm, 5 µ particle size)analytical column (Tokyo, Japan). The mobile phase consisted of 1.5 mM tetra-butyl ammonium bromide in deionized water:acetonitrile (40: 60, v/v) and was delivered at a flow rate of 1.0 mL/min. The injection volume was kept at 20 µL.

2.3. Laboratory scale synthesis of reactive dyes2.3.1. Synthesis of Reactive Red AThe detailed synthesis of Reactive Red A has been described in our earlier work (Patel et al., 2013). Briefly, 2 mol of H-acidwas reacted with 1 mol of cyanuric chloride under alkaline conditions and the reaction product obtained was coupled withdiazonium salt of sulfo vinylsulfone to obtain Reactive Red A in 98.2 % yield (Figure 1).

2.3.2. Synthesis of Reactive Red B (Scheme 1)Step 1: Solution A: 1 M aqueous solution of cyanuric chloride was prepared by dissolving 184.41 g in 1.0 L of ice cooledwater. Solution B: 1 M (300 g) alkaline solution of H-acid was made by dissolving 321g in 500 mL water and adding 53 gsodium carbonate. Solution A was then added drop wise in Solution B with continuous stirring over a period of 2 h by keepingthe reaction mixture at 0-5 0C to get the sintermediate Product X (yield 97.7 %). The reaction progress was monitored by TLCusing a mixture of ethyl acetate, n-propanol and water (2:6:2, v/v/v) as the solvent system (Rf value 0.53).Step 2: A diazonium salt of sulfo vinylsulfone was prepared by reaction with HCl and NaNO2 at 0-5 0C based on standardmethod (Vogel, 1996), and designated as the diazotized product (Scheme 1).Step 3: 1 mol of intermediate Product X was coupled with 1 mol of diazonium salt of sulfo vinylsulfone at pH 5.5-6.0 to obtainReactive Red B dye. The solution was rendered alkaline with 0.1M anhydrous sodium carbonate, followed by 7 % solution of

Figure 1Reactive Red A dye

Indian Journal of Science

Detergent:A detergent isa surfactant or a mixtureof surfactants withcleaning properties indilute solutions. They areusually alkylbenzenesulfonates, afamily of compounds thatare similar to soap but aremore soluble in hardwater.

Reactive dyes:Reactive dye is acompound which reactschemically with the fiberto form a strong covalentlinkage. They arecharacterized by areactive system,chromophoric groups,bridging group andsolubilising groups.



Page70sodium chloride and 9 % solution of potassium chloride (by volume) to recover the dye by salting. The solution was filtered,and the product obtained was dried and ground to fine powder (yield 97.9 %). The course of the reaction was monitored byTLC using a mixture of ethyl acetate, n-propanol and water (2:6:2, v/v/v) as the solvent system (Rf value 0.43).

2.3.3. Synthesis of Reactive Red C (Scheme 2)Step 1: This step was identical to the one described for Reactive Red B.Step 2: The diazonium salt of sulfo tobiaz acid was prepared by reaction with HCl and NaNO2 at 0-5 0C as described earlier(Vogel, 1996), and designated as the diazotized product (Scheme 2).Step 3: 1 mol of Product X was coupled with 1 mol of diazonium salt of sulfo tobiaz at pH 5.5-6.0 to obtain Product Y (dichlorotriazine dye).Step 4: This product X was then reacted with sulfo vinylsulfone at 40-45 0C temperature and maintaining a pH between 5.0and 5.5. After completion of the reaction, the solution was made slightly alkaline with 0.1M anhydrous sodium carbonate,followed by 7 % solution of sodium chloride and 9 % solution of potassium chloride (by volume) to obtain the dye by salting.The solution was filtered, and the product obtained was dried and ground to fine powder (97.2%). The course of the reactionwas monitored by TLC using a mixture of ethyl acetate, n-propanol and water (2:6:2, v/v/v) as the solvent system (Rf value0.48).

2.4. Dyeing of cotton fabricDyeing of cotton fabric was carried out using the method suggested previously (Fergusson, 2008; Ciba Speciality Chemicals,2005). For the dyeing experiments, bleached cotton fabrics of 10 × 4 cm dimension were used. After washing in solutioncontaining 2 mL/dm3 non-ionic detergent, the fabric samples were washed repeatedly in water and dried at room temperature.Prior to dyeing all fabric samples were wet in cold water. The dye bath contained 1% dye together with 80 gm NaCl and 20gm Na2CO3 per litre of solution. Due to high water solubility, it was possible to carry out application processes with a liquorratio of 1:5 of NaCl per L of dye bath as compared to 1:8/10 ratio commercially applied. The dyed samples were dried at roomtemperature before measurement.

2.5. Determination of dye exhaustion, dye fixation and fixation yield

Scheme 1Synthesis of Reactive Red B dye




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A detailed description on primary and secondary dye exhaustion, dye fixation ratio and fixation yield was similar to the onereported in our previous work (Patel et al., 2013). These parameters were evaluated and compared with reference reactivedyes under identical conditions. Reactive Red BS, Reactive Red M5BVS and Reactive Red ME4BL were used as comparisonstandards for Reactive Red A, Reactive Red A and Reactive Red C respectively. The percentage of dye bath exhaustion wascalculated by the equation,

% E = (C1-C2/C1) ×100

Where, ‘E’ is the degree of dye exhaustion from the dye bath, in percentage; C1 and C2 are the concentration of the dyebefore and after dyeing, respectively.

Fixation ratio is defined as the percentage of the dye chemically bound to cellulose at the end of the dyeing process, relativeto secondary exhaustion. Fixation yield is the percentage of dye chemically bound to cellulose at the end of the dyeingprocess, relative to the amount of dye used for the experiment. The following equation was used to calculate the dye fixationratio for all the dyes,

T = (C1/C2) ×100, where, T is the fixation ratio in percentage; C1 and C2 the concentration of the dye after and beforeextraction, respectively.

The fixation yield for dyeing was calculated using the formula,F=T × E/100, where F is the fixation yield in percentage

2.6. Measurement of colour fastnessThe performance of dyed cotton fabric for shade change and staining of adjacent fabrics due to washing, rubbing, exposure tosunlight and perspiration was assessed against the International Geometric Grey Scales (Imperial Chemical Industries, 1954).The values assigned for these properties were, 5 - Negligible change (Excellent), 4 – Slight change (Good), 3 - Noticeablechange (Fairly good), 2 - Considerable changed (Fair), 1 - Enormous change (Poor).

3. RESULTS AND DISCUSSIONFading of cotton textiles in presence of light is a perennial problem facing the dyers and technologists for more than a centurynow. Textile dyes in general are influenced by light, certain gases like oxides of nitrogen and moisture. Reactive dyespossess high fastness to wet treatments but their performance is affected in presence of light. Moreover, majority of hometextiles are usually exposed to sunlight under wet condition following laundering. The light fading of reactive dyes on cottonhas been investigated previously (Rastogi et al., 2001). They observed that light fastness is affected by the nature and degreeof dye fiber interaction. Further, bi-functional reactive dyes give superior performance than mono-functional dyes due to theformation of fiber-dye-fiber cross-links within the fiber micro structure. The degradation of this interaction is commonlyassociated with photo-oxidation via singlet oxygen (Griffiths and Hawkins, 1977). Typically, if a dye is attacked by a singlet

Scheme 2Synthesis of Reactive Red C dye


Colour fastness:It is a term used in thedyeing of textilematerials, signifyingresistance of thematerial's colour tofading. Light fastness,wash fastness, and rubfastness are the mainindicators that arestandardized.



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oxygen, light fading of the dye can start to occur. This condition ispossible due to the presence of peroxy - forming compounds likesodium perborate or sodium percarbonate in the detergent

1O2 + Dye → Decomposed dye

The fading mechanism of commercial reactive dyes on cotton has alsobeen studied by Unilever, a global detergent manufacturer (Batchelor etal., 2003). They concluded that the effect of moisture on the rate offading was faster in the pH range 3.0-8.0 compared to dry fabric. Inanother study, it was found that in the dry state or in the presence ofartificial perspiration the fading mechanism was reductive, whileoxidation occurs in the presence of water (Zhung et al., 2007).

Basically the cleaning action involves the following functions(Marsh, 1956), (a) lowering of surface tension of water, (b) wetting of thesolid surface of fabric, (c) penetration of water into the porous solid, (d)removal of dirt or grease and (e) suspension/dispersion of removed dirt,grease and fatty material. Further, laundry cleaning processes havesignificant impact on the performance of a dyed fabric. Thus, it is usefulto understand the variables in domestic laundering for practicalpurposes. Some important variables include, liquor ratio (volume ofdetergent solution to weight of fabric), number of rinse cycles, type ofdetergent and its alkalinity, pH of wash liquor, temperature of washingconditions, mechanical washing action and others. Thus, in the presentwork mono (sulfo vinylsulfone) and bi-functional (sulfo vinylsulfone andsulfo tobiaz acid) were synthesized to evaluate their fastness propertieson cotton fiber. The three reactive dyes were synthesized by derivatizing1-amine-8-hydroxynaphthalene-3,6-disulphonic acid with sulfovinylsulfone and/or sulfo tobiaz acid. The aim was to incorporate moresulphonic acid groups in the dyes for better color yield and increasedwater solubility. The purity of the dyes as assessed from UFLC analysiswas 98.2, 97.9 and 97.2 % for reactive red A, reactive red B andreactive red C respectively. The dyes were chromatographed on a BDSHypersil C18 (250 × 4.6 mm, 5 µ) column using 1.5 mM tetra-butylammonium bromide in deionized water: acetonitrile (40: 60, v/v) as themobile phase. Under the optimized conditions, the retention time forreactive red A, reactive red B and reactive red C were 16.675, 6.133and 9.477 min respectively as shown in Figure 2. The retention time forthe raw materials H-acid, sulfo vinylsulfone, sulfo tobiaz acid andintermediate product X was 7.797, 11.752, 6.040 and 13.685 minrespectively. The wavelength maxima (λmax) values for the synthesizeddyes and their comparison standards are shown in Table 1. Use ofsmaller liquor ratio (1:5), helps is reducing the salinity of the effluentafter the dyeing process. The degree of dye binding to the fabric wasconsiderably higher for the synthesized dye as compared to theircomparison standards as evident from their fixation yields (Table 1),mainly due to the presence of more reactive groups. Amongst the threedyes investigated, Reactive red A gave much higher fixation ratio andfixation yield compared to Reactive Red B and Reactive Red C (Table1).

3.1. Buffer capacity and alkalinity of commercialdetergentsDomestic as well as industrial laundry cleaning processes influence thefading of dyes due to exposure to light during drying or because of somechemical reactions which happen during washing of fabrics. Alkalis arecommon ingredients of commercial detergents which assist in removingoils, fats and waxes. Domestic detergents have varying contents ofalkali with some having oxygen generating bleaching agents such assodium perborate or sodium percarbonate. Sodium carbonate is atypical constituent which saponifies animal and vegetable fats and alsowaxes, thus allowing easy removal of oily substances. Other alkalinematerials like sodium silicate and sodium polyphosphates are added tobuffer the system for water hardness (Fergusson, 2008). Evaluation of

buffer capacity of detergents helps to recognize the effect of acidic or alkaline soil on fabric which could reduce detergentefficiency. The buffer capacity and alkalinity of four detergents used in the study was determined by titrating 0.1 % solution ofdetergents with 0.05 M sulphuric acid, which was standardized by sodium carbonate solution. The pH metric curves obtainedare presented in Figure 3. The initial pH of the detergents varied from 9.6-9.9. The pH curves for all the detergents showedgood buffering capacity between the pH range of 9.5-8.5 and 6.0-5.0. The steep part of the curves from pH 8.0-6.5 and pH4.0-2.5 indicates a fall in the buffer capacity to buffer the washing solution. The total alkalinity expressed as sodium carbonatewas 16.4 %, 16.9 %, 18.0 % and 12.7 % for Ariel, Rin, Surf Excel and Tide respectively.

3.2. Fastness to domestic washing

Figure 2UFLC chromatograms of Reactive Red A, Reactive Red B and Reactive RedC obtained on BDS Hypersil C18 (250 × 4.6 mm, 5 µ) analytical column



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Table 4Fastness to dry and wet rubbing of dyed cotton fabric

Dyed Cotton Dry Wet30 min 60 min 90 min 30 min 60 min 90 min

Reactive Red A 5 5 5 5 5 5Reactive Red B 5 5 4-5 5 4-5 4-5Reactive Red C 5 5 5 5 5 5

The colour fastness of dyes was determined by way of mechanical hesitation of cotton fabrics in four different commerciallyavailable detergents sold under the brand name Ariel, Rin, Surf Excel and Tide. A 10 × 4 cm piece of the dyed fabric wastaken and sandwiched between two adjacent fabrics and stitched. The sample and the adjacent fabric were washed togetherusing 1: 50 liquor ratio (washing detergent: water). After the treatment, the specimen was removed, rinsed twice in cold waterand then in cold running tap water. The pH of the final rinse was between 7.2-7.4. Further, it was squeezed and dried in air ata temperature not exceeding 60°C. The colour fastness was evaluated with the help of grey scales and the results at 1, 2 and3 h after drying are shown in Table 2. Further, this wash and exposure cycle (washing, rinsing and drying) was repeated 10times and the results for each cycle are illustrated in Figure 4. Apparently there was no significant change in the shade evenup to 10 cycles of washing and drying.

3.3. Fastness to sunlightAfter washing process, the fabrics were removed, separated and dried in sunlight, which is a common procedure in adomestic setting for different time durations. The change in colour of the specimen was compared with a standard in anidentical manner using the grey scale. The results for fastness to sunlight for different exposure time are summarized in Table3.

3.4. Fastness to rubbingTo test for fastness to rubbing, it is necessary to use standard Crock meter cloth, maintain a uniform pressure for applyingrubbing strokes and number of strokes. Further, for wet rubbing, % moisture on the crock‐cloth has to be maintainedbetween 65-70 %. Results for rubbing fastness (dry and wet) using the grey scale are presented in Table 4.

3.5. Fastness to perspirationThe fastness of reactive dyes with reference to alkaline and acidic perspiration was evaluated by using an alkaline (pH 8.0)and acidic (pH 5.5) liquors. To ensure uniform penetration of the solution, the fabric was dipped for 30 min in both the liquorsseparately. After which the liquor was removed and the excess water was removed by passing the specimen between twoglass rods. Composite specimens were then placed between acrylic plates with a pressure of 12 kPa perspirometer. The

Table 1Degree of dye exhaustion from the dye bath, dye fixation ratio and fixation yield

DyeWavelength

maxima(λmax)

Degree of exhaustion, %Fixation ratio, % Fixation yield, %Primary

exhaustionSecondaryexhaustion

Reactive Red BS 550 nm 52.5 69.2 74.2 51.3Reactive Red A 540 nm 60.2 87.4 85.4 74.6Reactive Red M5BVS 510 nm 40.4 60.6 66.2 40.1Reactive Red B 520 nm 55.8 71.2 74.8 53.2Reactive Red ME4BL 520 nm 41.6 68.2 54.7 37.3Reactive Red C 530 nm 45.2 70.3 70.3 51.4

Table 3Effect of sunlight on color fastness of dyed cotton fabric

DyeExposure time

Ariel Rin Surf Excel Tide2 h 4 h 6 h 2 h 4 h 6 h 2 h 4 h 6 h 2 h 4 h 6 h

Reactive Red A 5 5 5 5 5 5 5 5 5 5 5 5Reactive Red B 5 5 4-5 5 5 4-5 4-5 4-5 4-5 5 4-5 4-5Reactive Red C 5 5 5 5 5 4-5 5 5 4-5 5 5 5

Table 2Effect of different detergents on washing fastness of dyed cotton fabric

Dye Ariel Rin Surf Excel Tide1 h 2 h 3 h 1 h 2 h 3 h 1 h 2 h 3 h 1 h 2 h 3 h

Reactive Red A 5 5 5 5 5 5 5 5 5 5 5 5Reactive Red B 5 5 4-5 5 5 4-5 5 4-5 4-5 5 5 4-5Reactive Red C 5 5 5 5 5 5 5 5 4-5 5 5 5

Table 5Fastness to perspiration of dyed cotton fabric

Dye Perspiration FastnessAcidic liquor Alkaline liquor

Reactive Red A 5 5Reactive Red B 4-5 4-5Reactive Red C 5 5



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perspirometer was kept at 37 °C temperature for 4 h. Subsequently,the fabrics were removed, separated and dried in air below 60°C.The results for acidic and alkaline perspiration fastness aresummarized in Table 5.

4. CONCLUSIONTo summarize, three newly synthesized reactive dyes were studiedto evaluate their fastness properties on 100 % cotton fabric duringdomestic washing, exposure to sunlight, rubbing and perspirationusing four commercial detergents in the Indian market. The fixationratio and fixation yield of all the dyes were considerably highercompared to their reference standards. The conditions of washing,rubbing and drying were optimized to resemble the manner that isfollowed in a typical household. Domestic detergents do containvariable proportion of additives which contribute to colour fading ofdyed fabric. The results indicate comparable performance of all thethree dyes for the studied parameters. However, the colour fastnessproperties of dyed fabric were superior during domestic washingand exposure to sunlight with Ariel, Rin, and Tide detergentscompared to Surf Excel. This could be due to the presence of higheramounts of oxygen generating bleach in Surf Excel detergent.

Figure 3Buffer capacity curves (pH versus mL of 0.05 M H2SO4 solution) of four commercial detergents

Figure 4Colour fastness on repeated washing of the fiber(cycle 1-10) dyed with Reactive Red A, ReactiveRed B and Reactive Red C



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SUMMARY OF RESEARCH1.The synthesized mono- and bi-functional reactive dyes (Red A, Red B and Red C) form strong bond with the cotton fabric which gives rise to high

performance to wet treatments such as laundering with four commercial detergents.2.The reactive dyes gave higher fixation yields compared to their respective standards.

FUTURE ISSUESIt would be interesting to study the effect of optical brightening agents separately on the fading of these dyes under sunlight and wet conditions.

DISCLOSURE STATEMENTThere is no financial support for this research work from any funding agency.

ACKNOWLEDGMENTThe authors wish to thank all our colleagues for their constructive criticism and assistance towards successful completion of the work.

REFERENCE1. Batchelor S N, Carr D, Coleman C E, Fairclough L, Jarvis A. The photofading mechanism of commercial reactive dyes on cotton,

Dyes & Pigm. 2003, 59, 269-2752. Broadbent A D. Basic Principles of Textile Coloration, Society of Dyers and Colorists, West Yorkshire, 20013. Ciba Speciality Chemicals Inc., Cibacron S Reactive Dyes, Ciba Speciality Chemicals Inc. Oct., 20054. Fergusson S M. The effect of laundary detergents and residual alkali on the light fastness of reactive dyes on 100 % cotton,

Master’s Thesis, Diploma Textile Industries, RMIT University, Leeds, 20085. Finch R. Ed., Reactive Dyes, UK: Imperial Chemical Industries, 1979, pp. 6-116. Giwa A, Nkeonye P O, Bello K A, Kolawole E G. Solar photocatalytic degradation of reactive yellow 81 and reactive violet 1 in

aqueous solution containing semiconductor oxides. Int. J. Appl. Sci. Tech. 2012, 2, 90-1057. Griffiths J, Hawkins C. Oxidation by singlet oxygen of arylazonaphthols exhibiting azo–hydrazone tautomerism, J. Chem. Soc.

Perkin Trans. 2, 1977, 747-752.8. Ikiz Y, Keskin R. Fastness and PF/3 evaluations of reactive dyestuffs. Sci. Res. Essays, 2011, 6, 1498-15069. Imperial Chemical Industries, The Fastness Assessment of Textile Dyestuffs, 2nd ed.: Imperial Chemical Industries Dyestuff

Division, UK, 1954, pp. 19-2010. Kanazawa H, Watanabe M, Nogi T, Ohtaki Y. Chemical modification of cotton fabrics 2. Preparation and application of cotton

fabrics containing cellulose sulfonate or cellulose tosylate, Sci Rep. Fukushima Univ. 1986, 38, 45-5311. Lee Y H, Pavlostathis S G. Decolorization and toxicity of reactive anthraquinone textile dyes under methanogenic conditions,

Water Res. 2004, 38, 1838-1852.12. Marsh J T. An Introduction to Textile Bleaching, London: Chapman & Hall Ltd., 1956, p. 12513. Mazumdar S, Haque M M. Importance of fixing agent on the colour fastness of reactive dyestuff originated from various dye

manufacturers, Pak. Text. J. 2011, 44-4714. Ojstrsek A, Doliska A, Fakin D. Analysis of reactive dyestuffs and their hydrolysis by capillary electrophoresis, Anal. Sci.

2008, 24, 1581- 158715. Patel J. R, Patel M.H, Shrivastav P S, Sanyal M. Synthesis of a modified reactive dye with improved dyeing performance on

cotton fabric and its degradation study, Ind. J. Sci. 2013, 3, 45-5116. Rastogi D, Sen K, Gulrajani M. Photofading of reactive dyes on silk and cotton: effect of dye-fibre interaction, Color. Tech. 2001,

117, 193-19817. Shore J. Cellulosic Dyeing, Society of Dyers and Colorists, Bradford, 199518. Srivastva S B. Recent Process of Textile Bleaching Dyeing and Finishing, Small Business Publications, Delhi, 2003, pp.5219. Vogel A I, Tatchell A R, Furnis B S, Hannaford, Smith P W G. Vogel’s Textbook of Practical Organic Chemistry, 5th Edition,

Prentice Hall, London, England, 199620. Woodhouse J M. Science for Textile Designers, London: Elek Science, 1976, p.15621. Zhung D, Zhang L, Pan D, He J. Fading of reactive dyes on cellulose under light and perspiration, Color. Tech. 2007, 123, 80-85

Ojstrsek et al. (2008):The objective of thepresented research wasto examine the potentialof capillaryelectrophoresis (CE) forthe analysis of structurallydifferent reactivedyestuffs, their activationand posterior hydrolysis,with special focus onoptimization of theworking conditions.Preliminary, the effect ofvarious additives to thebackground electrolyte onthe resolutionimprovements versusmigration time of ReactiveBlack 5 as a modeldyestuff was investigated.Based on these results,the electropherograms ofeight commerciallyinteresting reactivedyestuffs of variouschemical structures andtheir converted formsupon alkaline pH werecarried-out. In order toexamine the behavior ofthe reactive dyestuffduring the dyeingprocess, the dye-bathabsorbance wasmonitored throughout theReactive Black 5exhaustion, and theconversion of the dye'sform was highlightedusing the CE technique.The obtained resultsunequivocally prove thatCE could offer a fast andefficient detection methodof structurally differentreactive dyestuffs, as wellas their hydrolysisproducts in the dye-bathsand effluents later on.

RESEARCH • CHEMISTRY 49 77 Science

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