Workow: Annotated pdf, CrossRef and trackedchangesPROOFCOVER SHEETAuthor(s): MansourRymArticletitle:Dyeingpropertiesof cationized and non-cationizedcottonfabricsdyed withVitisviniferaL. leavesextractArticleno: TJTI 1046289Enclosures: 1) Querysheet2) ArticleproofsDearAuthor,1. Please check theseproofs carefully. It is the responsibility ofthe corresponding authortocheck these and approveor amendthem.A secondproof is not normallyprovided. Taylor & Francis cannot be held responsiblefor uncorrectederrors, evenif introducedduring the productionprocess.Once yourcorrections havebeenadded tothe article,it willbeconsidered readyfor publication.Pleaselimit changes at thisstage tothe correction of errors. 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PleasealsoseeourFAQshere:http://journalauthors.tandf.co.uk/production/index.asp.5. Makesurethatyousavethe lewhenyouclosethedocumentbeforeuploadingittoCATSusingtheUploadFilebuttonontheonlinecorrectionform. Ifyouhavemorethanonele, pleasezipthemtogetherandthenuploadthezip le.If you prefer, you canmake yourcorrections using the CATS onlinecorrectionform.TroubleshootingAcrobat help: http://helpx.adobe.com/acrobat.htmlReader help: http://helpx.adobe.com/reader.htmlPleasenotethat full user guides for earlier versions of theseprograms areavailablefromtheAdobeHelppages byclicking on the link Previous versions under the Help and tutorials heading fromthe relevant link above.Commentingfunctionalityis available fromAdobe Reader 8.0 onwardsand fromAdobe Acrobat7.0 onwards.Firefoxusers: Firefoxsinbuilt PDFViewer isset tothedefault; pleaseseethefollowingfor instructionsonhowtousethis anddownloadthePDFtoyour harddrive: http://support.mozilla.org/en-US/kb/view-pdf-les-refox-without-downloading-them#w_using-a-pdf-reader-pluginDyeing propertiesof cationized and non-cationized cotton fabrics dyed with Vitis vinifera L.leaves extractMansourRyma*, MhenniFaroukaand EzziliM.Bechirb5aFacult de sciences de Monastir, Unit de recherche Chimie applique et environnement UR13ES63, Monastir, Tunisie;bCBBCTechnoparc Borj Cidria,Hammam Lif, Tunisia(Received 2 September 2014; accepted23 April 2015)Thisstudylaysbaretwomainobjectives. Therst istodeterminetheamount of anthocyaninsintheleavesof VitisviniferaL.bythespectrophotometricmethodandthesecondistodyecationizedandnon-cationizedcottonfabricswith10 the V. viniferaL. leaves aqueous extract.We have thoroughly investigatedthe effects of dye bath pH and temperatureonthedyeingproprietiesoftheaforementionedfabrics.Thecolorstrength(K/Svalue)ofdyedcationizedcottonfabrics(K/S = 12)hasbeenbetterthanthenon-cationizedones(K/S = 4). Experimentalresultsshowthatthefastnesspropertiesofdyedcationizedcottonfabricsrangefromaveragetogood. Wendthat thecationizationofcottonfabricshaslargelyimproved the dyeabilityand fastness properties of cotton fabrics dyed with V. vinifera L. leaves aqueous extract.15 Keywords: Vitis viniferaL. leaves; anthocyanins; cationized cotton;dyeing; fastnessIntroductionTheuseofplants, seashells, andcoccidinsectstocreatecoloriscommontoallcivilizations(Adeel,Ali,&Zsila,2009). Withtheadvent of widelyavailableandcheaper20 syntheticdyesin1856;theuseofnaturaldyeswithpoortomoderatewashandlight fastnessdeclineddrasticallyandwas replacedbymore moderate toexcellent colorfastness properties of synthetic materials. Yet, it isprimordial tonote that the revival of natural dyes was25 mainlyduetothehazardousandcancerogenicnatureofsyntheticdyes.VitisviniferaL.isawoodywinter-deciduousclimberwith tendrils attaching to surrounding plants. It isgenerally believed to be native to southwestern Asia.30 The leaves are alternating, palmately lobed, 520 cmlongandbroad. Theleavesof V. viniferaL. arerichintannins, avonoids, procyanidins and also containorganic acids, lipids, enzymes, and vitamins(Bombardelli&Morazzonni, 1995;Hmamouchi, Lahlou,35 Es-Sa, & Agoumi, 1998). Vine leaves turn red inautumn and their ushing intensities depend on theperiodofcollection(Felicio, Santos, &Gonalez, 2001).The main coloring agents in V. vinifera L. leaves areanthocyanins: monoglucoside cyanidin, monoglucoside40 peonidin, and monoglucoside malvidin (Monagas,Garrido, Bartolom, &Gmez-Cordovs, 2004; Rym,Bechir, & Farouk, 2013). Moreover, anthocyaninsproductioninV. viniferaL. leavesincreasesinresponsetosurgingsugar concentrationsinautumn. Inthiswork,45 V. viniferaLleaveswerecollected, extractedwithwater,and studied to explore their potential applications asnatural dyes intextileindustry.Generally, leaves containing primarily anthocyaninsappear red, while those with large amounts of both50 anthocyanins and carotenoids have orange color.However, leaves with carotenoids, and little or noanthocyanins are yellow. Anthocyanins containanthocyanidins (or aglycons) whicharebasicfunctionalchemical structures in anthocyanins (Bombardelli &55 Morazzonni, 1995). Whenanthocyanidinsarebondedtoasugar moiety, theyareknownascyanidins. Cyanidinsare important coloring components of V. vinifera Lleaves (Figure 1). Cotton can be easily dyed, but thecellulosedyebondisnot verystrong. Natural cellulose60 bersarenegativelychargedbecauseof thepresenceofcarboxyl and hydroxyl groups (Izabela &Wei, 2004).Usingcommercial cationicagentsinthepretreatment ofcotton may enhance dye absorption and can not onlyincreasethedyeingcolorstrengthbutalsoimprovewash65 fastness (Burkinshaw&Gotsopoulos, 1996). Cationicmodication is a method that has been employed inorder to change the surface charge of cellulosic bers(Chen, Zhao, &Wang, 2004; Kim&Sun, 2002; Rong&Feng, 2006; Wu&Kuga, 2006). Inthesestudies, a70 variety of cationic agents with amino, ammonium,sulfonium, phosphonium, and other groups have beenemployedtomodifycellulosefabrics, thehighcost, thefabric yellowing and toxicity of these substances haveprevented their industrial applications. The 3-chloro-2-75 hydroxypropyl trimethyl ammoniumchloride(CHPTAC)AQ1 AQ2AQ3AQ4*Corresponding address. Email:rymmansour2004@yahoo.fr 2015The Textile InstituteThe Journal of The TextileInstitute, 2015http://dx.doi.org/10.1080/00405000.2015.1046289TJTI 1046289 CE: QA:16 May 2015 Coll: QC:Revisionis areasonablycheap, reactive, andlow-toxicchemicalwhich is probably a good cationic agent for themodicationof cellulosicbers(Liu, Yang, Zhang, Liu,&Xiong, 2007). Inshort, thefocusof thisarticleisto5 investigate the dyeing behavior of cationized andnon-cationized cotton with V. vinifera L. leaves aqueousextract.Materials and methodsV. vinifera L. leaves identication10 TheV. viniferaL. BlackGrenacheleaveswerecollectedfromBirBouRagueba, asuburbinthecityofNabeul,Tunisia. Bir BouRaguebas latitude is 1025 and itslongitude is 3637W. Leaves were lyophilized andreducedto ne powder.15 LyophilizationThe leaves were removed from the trees andimmediatelyput onice. Majorveinswereremovedwitha razor blade and discarded. The leaves were cut intosmall pieces (2 cm2), frozen in liquid nitrogen, and20 groundwithamortarandpestle. Thepowderwaseitherextracted immediately, or lyophilized, or oven dried at40Cor at 90C. Thepowder represents 90%of theV.viniferaL. leavesamount.Extraction25 V. vinifera L. leaves are boiled in 100 mLof distilledwater for 60 minat the temperature of 95Cat a bathratioof 1/20(1 gof plant material extractedby20 mLof distilled water). The dye baths were ltrated andcooled.30 Characterizationof the cotton fabricsCommerciallybleachedcottonfabricwiththefollowingspecications was suppliedfromSITEX, Tunisia; plainweave (plain weave and weight, 150 g m2), thicknesswas 0.261 cm mm1, number of yarns cm1in warp35 directionwas 43andinweft directionwas 42. Beforedyeing, thefabricwastreatedwithasolutioncontaining5 g L1non-ionic detergent, at 50Cfor 30 min. Then,thefabricwasthoroughlyrinsedwithwaterandairdriedat room temperature.40 Cationization of cotton withCHPTACDesized, scoured, and bleached plain woven cottonfabric was used in this work. The cationic agent(CHPTAC) 3-chloro-2-hydroxypropyl trimethylammoniumchlorideiscommerciallyavailableasa65%45 aqueous solution and was purchased from Fluka.Reagent-grade NaOH crystals and hydrochloric acid(HCl) were purchasedfromFluka. Distilledwater wasused throughout theexperiments.Cationization of the cotton fabric50 Cationized cotton was prepared by using CHPTACtoinsert cationic groups on the surface of cotton bers.The reaction of cationic agent with cotton in thepresence of alkaline catalyst yields cationic cotton(Kevin, Hong, &Juan, 2007). Intheexhaustionmethod,55 at 30:1liquor ratio, cationic agent solutionwas mixedwith water to prepare a bath containing cationic agentwith 20% w/w ber samples. The samples wereintroducedintothebathand, after5 mindwell time, thetemperature was increased fromambient to 60Cat 260 2.5C min1and then held constant during thecationizationprocess. Thebathwaswell agitatedduringtheprocess. Afterthat, 15%onweight offabric, sodiumhydroxide (40 g L1) was added in three steps every5 min, and after the last addition the mixture was65 agitated for 10 min. At the end of the reaction, thesamples were removed fromthe bath, rinsed severaltimes with water, and acidied with 1%acetic acid.They were then again rinsed with water and dried atambienttemperature.70 Fourier transform infrared spectroscopic analysisFourier transforminfrared(FTIR) spectrawererecordedonaNexus 470FTIRSpectrometer, Nicolet Company,USA, using potassiumbromide disks. Atotal of 32scans for eachsample were takenwitha resolutionof75 4 cm1, witha rangeof 4000400 cm1.The dyeingprocessDyeingwasperformedby theexhaustionmethod usingaliquor ratio of 20:1, with the cotton fabric dyed inlaboratory dyeing machine (Ahiba DatacolorFigure1. Chemicalstructureofoneofthecolorcompositionsof V. vinifera L. leaves extract dye: Cyanidin-3-oglycoside.AQ52 M. Rym et al.TJTI 1046289 CE: QA:16 May 2015 Coll: QC:Revision5 International, USA) at different pHvalues (28) andatdifferent temperatures (4595C). The pHvalues wererecordedwithEutechpH-meterinstrumentsandadjustedwith acetic acids and dilute solution of sodiumhydroxide0.1 N. Thetemperaturewasraisedat constant10 value(4595C) over 30 minandheldat this level for90 min. The dyeing was carried out in the laboratorydyeingmachine(AhibaDatacolour International, USA).Then, thedyedfabricswereremoved, rinsedwithwater,followedbyasoapingstepusing3 g L1ofanon-ionic15 detergent (4-Nonylphenyl-polyethyleneglycol non-ionic)at 60Cduring5 min. Finally, the fabric samples werewashedthoroughlywithcoldwater, squeezed, anddriedat room temperature. The dyeing experiment wasperformed in duplicate.20 Evaluation of dyeingqualityThe reectance and the L, a*, b* values of the dyedsamples were measured with a Spectro Flash SF300spectrophotometer (illuminant D65/10o observer) withdata.25 Master 23 software (Datacolor International, USA).Relative color strengths (K/S values) were determinedusing theKubelk and Munkequations.The color yield (K/S) values were calculated byKubelka Munkequation(Kubelka& Munk, 1931):KS 1 R 22R1 R0 22R0; (1)30 where R is the decimal fraction of the reectance ofdyedfabric, R0isthedecimal fractionofthereectanceofundyedfabric, KistheabsorptioncoefcientandSisthe scattering coefcient, L* is corresponding to the35 brightness(100 = white, 0 = black), a*iscorrespondingtothered/greencoordinate(positivesign = red, negativesign = green),andb*iscorresponding totheyellow/bluecoordinate (positivesign = yellow, negative sign = blue).Fastnesses testing40 Thedyedsamples wereevaluatedaccordingtoNFandISOstandard methods: ISO105-X12: 2002 for colorfastnesstorubbing;ISO105-C10:2006forcolorfastnesstowashing, andISO105-B02:1994forcolorfastnesstolight.45 Quantity of anthocyanins in V. viniferaL. (BlackGrenache) leavesby spectrophotometric methodA weightedamount ofplant material wasextractedwithdistilledwaterinabeaker.Inthestandardprocedure,themassof plant material/volumeof liquidratiowasset at50 1:20, i.e. 1 gofV. viniferaL. wasextractedwith20 mLof water. The extraction was performed forapproximately60 minat 95C. Theamount of extractedcoloredsubstancesasafunctionof timewasmonitoredby photometry. Total anthocyanins content was55 determinedusingthe pHdifferential assayof Giusti etWorlstad. Absorbances (A) were measuredphotometricallyintherange350700 nmusinga10 mmcuvette and CE 202 UVvisible diode arrayspectrophotometer. Absorbances at 520 and 700 nmin60 buffers at pH1 and 4.5 were used to calculate theconcentration of dyes as cyaniding-3-glycoside fromEquation (2).AA520 nmA700 nmpH 1:0 A520 nmA700 nmpH 4:5: (2)ACY A MWDF 103e l: (3)65 Monomeric anthocyanin pigment concentration in theextractwas then calculated according toEquation(2).The determined concentration can be transformedintodyecontent intheplant material bymultiplicationby a factor 20 (1 g of material extracted in20 mLof70 water).Here ACYis the monomeric anthocyanin pigmentconcentration calculated as mg cyaniding-3-glycosideL1extract, MWisthemolecular weight of cyandin-3-glycoside (449.2 g mol1), = 26,900 M extinction75 coefcient, in L mol1cm1, for cyd-3-glu; and103 = factorforconversionfromgtomg. DF = dilutionfactorestablishedinD;l = pathlengthincm(Leeetal.,2005).Results and discussion80 The anthocyanins concentration calculated, withspectrophotometric method, in the 20 mLof extract is191 mg L1whichisequal to3.82 mgof 1 gof dryV.viniferaL. leaves whichcorrelatedwithHPLCanalysisresults investigated in one of our studies. Therefore,85 anthocyanins(presentsthedyestuff)represents0.38%ofdry V. vinifera L. leaves(Rym et al.,2013).FTIR analysisFTIRspectra: theuntreated(A) andtreated(B), cottonfabricwithcationizingagent,areshowninFigure2.The90 treated cotton fabric (curve B) shows four absorptionbands at 2918.79, 2850.04, 1430.17, and1373.02 cm1correspondingtothealiphatic CHstretching. Abroadabsorptionbandwithlowintensityof theprimaryOHstretchingbandofuntreatedcottonfabricat3352.38and95 1032.71 cm1isobservedinspectrum(A). Furthermore,the absorption intensity of primary OH stretchingAQ6AQ7AQ8AQ9The Journalof The Textile Institute 3TJTI 1046289 CE: QA:16 May 2015 Coll: QC:Revisionnarrowbandat 3343.61 cm1whichisassociatedwithabandat 1033.05 cm1is considerablyincreasedincaseof the cationizedfabric relative tothe untreatedcotton5 fabric. Thetreatedsamplesshowedacharacteristicpeakat 1199.67 cm1due to CN stretching vibration.Effect of pHFigure3showsthat thepHvaluesofthedyebathhaveaconsiderableeffect onthedyeabilityof cationizedand10 non-cationizedcottonfabricswithV. viniferaL. extract.Notingthat, thepHofV. viniferaL. leavesextract itselfbeforepHadjustmentis4.6. It isclearthat cationizationhas improvedthedyeabilityof thefabrics at pH2and2.5 values. The acidic pH dye bath enhances the15 dyeabilityofcottonfabricespeciallycationizedonewithV. viniferaL. extract. Theeffect of dyebathpHcanbeattributed to the correlation between dye structure andcationized cotton ber. Since the V. vinifera L. leavesextract contains anthocyanins which are water-soluble20 dyescontainingmanyhydroxyl groups, it wouldinteractionicallywiththe protonatedterminal aminogroups ofcationized cotton bers at acidic pHvia ion exchangereaction. Thus, these kinds of interactions take placetogether with ionic forces. This ionic attraction would25 increase the dyeabilityof theber as clearlyshowninFigure 3.Effect of temperatureAsit iswell recognized, thedyebathtemperatureplaysanimportant roleindyeingwithnatural dyes. Acasein30 point, the stabilityof the anthocyaninpigments largelydependsontemperatureamongother factors(Leeet al.,2005). Table 1 shows the effect of the temperature ofdyeingonL*, a*, b*andK/Svalues of cationizedandnon-cationized dyed cotton. When dyeing temperature35 increased, thevaluesof L*decreasedandthevaluesofK/Sincreased. Thus, thehighest valueofL*andlowestvalue of K/S showed lighter shades, while both thelowest values of L* and the highest values of K/Ssignifydeeper shades of dyedsamples. Positivea*and40 positive b* represent red and yellow, respectively.Therefore, samples dyedat 45Chave higher value ofa*thanthosedyedat 95C. Theseresultscorrelatewithredandbrownshades of dyedfabrics, whichcouldbeexplainedbythetemperatureeffect onanthocyanins. As45 it expected, thedyeuptake of cationizedcottonfabrics(CC) isbetter thannon-cationizedones(NCC) whichismay be due to, rst, the ber swelling effects thatenhancethedyediffusion.Second,itcanbeattributedtothecorrelationbetweenthedyestructureandcationized50 cottonbers. Sincetheanthocyaninsact asanaciddye,it wouldinteract ionicallywiththe protonatedterminalaminogroupsofthecationizedcottonbersunderacidicmedium(pH 4) via electrostaticdye attraction.MonoforprintcolouronlineFigure 2. FTIRspectra: the untreated (A) and treated (B),cotton fabric with cationizing agent CHPTAC.MonoforprintcolouronlineFigure 3. Effect of dye bath pH on the color strength of cationized and non-cationized cotton fabrics dyed at 95C.4 M. Rym et al.TJTI 1046289 CE: QA:16 May 2015 Coll: QC:RevisionFastness properties5 The light, wash, and rubbing fastness values ofcationizedandnon-cationizedcottonfabricsdyedwithV.viniferaL. leavesaqueousextract areshowninTable2.The control sample shows good rubbing and washfastness properties of cationized dyed fabrics (3/4510 units onthegrayscalewhereas 5is thehigher rating).Thisresultcanbeexplainedbytheafnityofcationizedcotton ber to anthocyanins. The light fastness ofcationizedcottonfabricsisgood(6unitsonthestandardblue scale whereas 8 is the highest rating) which is15 better than those obtained with non-cationized cottonfabric. ThecationizedcottonfabricdyedwithV. viniferaL. leaves extract shows higher color strength than thenon-cationized cotton fabric because cationized cottonfabric contains more functional groups than the non-20 cationizedone.Infact,thecationizationofcottonfabricsenhances thegoodpenetrationof thecolor inthebermatrix. The value results obtained (Table 1) illustratethat non-cationized cotton shows a yellowish-browncolor; however, cationized cotton fabric shows redish-25 browncolor. It canbeconcludedthat cationizedcottonfabrics can be successfully dyed with V. vinifera L.leaves extract. Anthocyanins contain phenoliccompounds. The anionically charged phenolic groupscouldformanionicbondwithcationics(aminogroups)30 in thecationiccotton fabric.ConclusionThe purpose of this study was to valorize the dyeingpropertiesofcationizedcottonfabricdyedbyV. viniferaL. Leaves extract. Indeed, better K/S values were35 observedfordyedcationizedcottonfabricscomparedtothe results obtained of non-cationized ones. Even, atlower dyeing time and temperature the dye uptake ofcationized cotton fabrics is better than non-cationizedones dyedinhigher temperature andtime whichcould40 obviously presentthebenetofthealternative process asit could save time and energy. As it showed in thisstudy, cationizedcottonfabrics, dyedwithV. viniferaL.Leaves extract, have better fastness dyeing propertiesthan non-cationizedones.45 Disclosure statementNo potentialconict of interest was reported by the authors.ReferencesAdeel, S., Ali, S., &Zsila, F. (2009). Dyeingof cottonfabricusing pomegranate (Punica granatum) aqueous extract.50 Asian Journal of Chemistry, 21, 34933496.Bombardelli, E., &Morazzonni, P. (1995). Vitis vinifera L.Fitoterapia, 66, 291294.Burkinshaw, M., &Gotsopoulos, A. (1996). Pretreatment ofcottontoenhanceitsdyeability; Part 2. Direct dyes. Dyes55 Pigments, 32, 20092012.Chen, W., Zhao, S., &Wang, X. (2004). Improvingthecoloryield of ink-jet printing on cationized cotton. TextileResearch Journal, 74, 6871.Felicio, J., Santos, L., & Gonalez, E. (2001). Chemical60 constituents fromVitis viniferaL. (Vitaceae). Arquivos doInstituto Biolgico, 68, 4750.Hmamouchi, M., Lahlou, M., Es-Sa, N., & Agoumi, A.(1998). Molluscicidal properties of some proanthocyanidins,avones and avonols. Fitoterapia, 69, 161165.Table1. Effect of thedyeingtemperatureonL, a*, b*, anddepthof shadesvalues(K/S) of dyedcationizedandnon-cationizedcotton fabrics dyed with V. viniferaL. leaves extract.Temperaturesa* b* L K/SCC NCC CC NCC CC NCC CC NCC45 21 1.34 12 6.51 60 87.34 5.6 1.860 17.5 2.44 18.2 6.48 55 85.86 6.7 2.675 15.8 4.25 20 13.04 47 81.39 7.7 3.380 15.2 2.18 20.5 14.71 43.5 76.02 10.6 3.795 14 0.84 22 19.01 42 75.02 12 4CC: cationized cotton; NCC: non-cationized cotton; pH = 2.5.Table 2. Values of light, wash, and rubbing fastness of dyed cationizedand non-cationized cotton fabrics, at T = 95C; pH = 3.Wash fastnessLight fastnessRubbingfastnessActate Cotton Nylon PES PAC Wool D*W*Non-cationizedcotton fabric 5 5 5 5 5 3/4 2 4 Cationized cotton fabric 5 5 5 5 5 5 6 4 AQ10AQ11AQ12The Journalof The Textile Institute 5TJTI 1046289 CE: QA:16 May 2015 Coll: QC:Revision5 Izabela, K., & Wei, Z. (2004). Anthocyanins More than naturescolours. Journal of Biomed Biotechnol, 5, 239242.Kevin, H., Hong, D., &Juan, H. (2007). Effect of surfacecationization on the conformal deposition ofpolyelectrolytesover cotton bers. Cellulose,14, 615623.10 Kim, Y., &Sun, G. (2002). Functional nishingofacrylicandcationicdyeablefabrics intermolecular interactions. TextileResearch Journal, 72, 10521055.Kubelka, ., &Mnk, F. (1931). Ein Beitrag zur Optik derFarbanstriche HZ [A contribution to the appearance of15 coats of paint]. Techn Physik, 12, 593601.Lee, G., Robert, D., Ronalad, E., Barnes, K., Eisele, T., &Giusti, M. (2005). Determination of total monomericanthocyanin pigment content of fruit juices, beverages,natural colorants, andwinesbythephdifferential method:20 Collaborative study. Journal of AOACInternational, 88,12691272.Liu, Z., Yang, Y., Zhang, L., Liu, Z., &Xiong, H. (2007).Study on the cationic modication and dyeing of ramieber. Cellulose,14, 337345.25 Monagas, M., Garrido, M. I., Bartolom, B., & Gmez-Cordovs,C. (2004). Chemical characterizationof commercial dietaryingredients fromVitis vinifera L. AnalyticaChimicaActa,563, 401404.Rong, L., &Feng, G. (2006). Dyeing properties of PECH-30 aminecationizedcottonwith acid dyes. Journal of AppliedPolymer Science, 100, 33023306.Rym, M., Bechir, E., &Farouk, M. (2013). DyeingpropertiesofwoolfabricsdyedwithVitisviniferaL.(blackgrenache)leaves extract. Fiberand Polymer, 14, 786789.35 Wu, M., &Kuga, S. (2006). Cationizationof cellulosefabricsby polyallylamine binding. Journal of Applied PolymerScience, 100, 16681672.6 M. Rym et al.TJTI 1046289 CE: QA:16 May 2015 Coll: QC:Revision