Dyeing Of Polyester With Disperse Dyes: Part 1 .

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Int.J.Curr.Microbiol.App.Sci (2015) 4(5): 923-928ISSN: 2319-7706 Volume 4 Number 5 (2015) pp. 923-928http://www.ijcmas.comOriginal Research ArticleDyeing of polyester with disperse dyes: Part 1. Antimicrobial activity anddyeing performance of some disperse dyesAlya Al-Etaibi1*, Morsy Ahmed El-Apasery2 and Magda M. Kamel21Natural Science Department, College of Health Science, Public Authority for AppliedEducation and Training, Fayha, 72853, Kuwait2Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, NationalResearch Centre, 33 El Buhouth St., Dokki, Cairo, Egypt*Corresponding authorABSTRACTKeywordsPolyester amino-1-p-arylpropenones 3a,b coupled with phenyl diazoniumsalt to give the corresponding 3-oxo-2-(phenylhydrazono)-3-parylpropionaldehydes disperse dyes. Fastness properties of the dyes wereexamined against light, rubbing, perspiration and washing fastness. Thebiological activities of the synthesized dyes against Gram positive bacteria,Gram negative bacteria, yeast and fungi were also evaluated.Introductionanalogues. Al-Etaibi et al. (Al-Etaibi et al.,2012; and 2011) reported the syntheses ofdifferent azo disperse dyes based onenaminones for polyester fabrics. Recently,other studies reported the application ofsynthesized azo dyes for dyeing and printingpolyester fabrics (El-Molla et al., 2013;Elattar, et al., 2013). Thus, we have initiateda program of applying the synthesized dyesderived from enaminones to polyester asdisperse dyes to study their colourmeasurement, fastness properties andantimicrobial activities.Azo disperse dyes are a versatile class ofcoloured organic dyes and receive aconsiderable attention, as a consequence oftheir exciting biological properties and theirapplications in various fields, e.g., textiles,leathers, papers, additives, and cosmetics(Abdou et al., 2013; Zollinger, 2003; Klaus,2003). Considerable studies have beendevoted to azo dyes derived from 3dimethylamino-1-p-arylpropenones(ElApasery, et al., 2011; Hajós, et al., 2008;Al-Saleh, et al., 2004). The azo dispersedyes based on enaminones result in brighterand deeper shades than their benzene923

Int.J.Curr.Microbiol.App.Sci (2015) 4(5): 923-928polyester fabrics were added. Dyeing wasperformed by raising the dye bathtemperature to 130 C for 60 min underpressure in an infra red dyeing machine.After dyeing, the fabrics were thoroughlywashed and subjected to surface reductionclearing ((2 g NaOH 2 g sodiumhydrosulphite)/L, and soaped with 2%nonionic detergent to improve washingfastness). The samples were heated in thissolution for 45 min at 80 C. Rinse well incold water and neutralize with 1g/L aceticacid for 5 min at 40 C, the dyed sampleswere removed, rinsed in tap water andallowed to dry in the open air.ExperimentalGeneral procedure for the synthesis ofazo disperse dyes (5a,b)A cold solution of the diazonium salt (10mmol), prepared by adding a cold solutionof sodium nitrite (0.7 g) in water (10 mL) toa solution of aniline (10 mmol) in conc.hydrochloric acid (4 mL), was added to acold solution of 3-dimethylamino-1-parylpropenones 3a or 3b (10 mmol) inethanol (15 mL) containing sodiumhydroxide (1.2 g). The resulting mixture wasstirred at room temperature for 30 min. Theprecipitate that formed was collected byusing filtration and crystallized fromethanol. Dyes 5a,b was confirmed by thereported data (Al-Shiekh, et al., 2008;Hajós, et al., 2008; Al-Awadi, et al., 2001).Colour measurementsThe colorimetric parameters of the dyedpolyester fabric was determined on areflectance spectrophotometer. The colouryields of the dyed samples were determinedby using the light reflectance techniqueperformed on UV-Vis spectrophotometer.The colour strengths, expressed as K/Svalues, were determined by applying theKubelka-Mink equation (Al-Etaibi et al.,2014a).High temperature dyeing method (HT)MaterialsScoured and bleached 100% polyester fabric(149 g\m2) was supplied by El-Mahalla ElKobra Company. The fabric was treatedbefore dyeing with a solution containingnon-ionic detergent 5 g/L (Hostapal,Clariant) and sodium carbonate (2 g/L) in aratio of 50:1 at 60 C for 30 min, thoroughlywashed with water, and air dried at roomtemperature.K/S [(1R)2 / 2R][(1Ro)2 / 2Ro]where R decimal fraction of thereflectance of the dyed fabric; Ro decimalfraction of the reflectance of the undyedfabric; K absorption coefficient; S scattering coefficient.DyeingA dispersion of the dye was produced bydissolving the appropriate amount of dye(2% shade) in 1 mL dimethylformamide andthen added drop wise with stirring to the dyebath (Liquor ration 50:1) containing sodiumlignin sulfonate as dispersing agent. Theratio of dispersing agent to dyestuff is 1:1.The pH of the dye bath was adjusted to 4.85using aqueous acetic acid and the wetted-outFastness testsFastness to washingAfter washing using 5 g/L of the non-ionicdetergent (Hostapal, Clariant) and 2 g/L ofsodium carbonate, the dyed fabrics weretested by using ISO standard methods(Chrysler et al., 1990). A specimen of dyed924

Int.J.Curr.Microbiol.App.Sci (2015) 4(5): 923-928polyester fabric was stitched between twopieces of undyed cotton and wool fabrics, allof equal length, and then washed at 50 Cfor 30 min. The changes in color wereassessed according to the gray scale (AlMousawi et al., 2014).assessed according to the blue scale(Chrysler, 1990).Antimicrobial Activities TestThe antimicrobial activities of disperse dyeswere tested using Agar-well diffusiontechnique (Al-Etaibi et al., 2014b), againstsix different microbial cultures. PureculturesofBacilluscereusandStaphylococcus auerus (Gram positivebacteria),EscherichiacoliandPseudomonas aeruginosa (Gram negativebacteria), Candida albicans (Yeast) andAspergillums Niger (Fungi) were involvedin the test. An aliquot of 0.1 mL of eachbacterial strain was inoculated and spread onnutrient agar (NA) while 0.1 mL of the yeastand fungi were spread on potato dextroseagar (PDA). The inoculated plates weresupplied with 100µl of each of the testeddisperse dyes with a total final concentrationof 100mg ml-1. The disperse dyes wereincluded in 6 mm wells produced by sterilecork borer. The NA plates were incubatedat 37 C for 24 hours while PDA plates wereincubated at 25 C for 24-48 h. The zones ofinhibition around the wells were determined.Picture were taken for some of the platesafter 24 and 120 h using digital camera todetermine the nature of the dyes if they werecytolytic or cytostaticFastness to perspirationThe samples were prepared by stitching apiece of dyed polyester fabric between twopieces of cotton and wool fabrics and thenimmersed in the acid or alkaline solution for30 min. The acid solution (pH 4.5) containssodium chloride (10 g/L), sodiumdihydrogen orthophosphate (1 g/L) and Lhistidine monohydrochloride monohydrate(0.25 g/L). The alkaline solution (pH 8.7)contains sodium chloride (10 g/L), disodiumorthophosphate (1 g/L) and L-histidinemonohydrochloride monohydrate (0.25 g/L).The changes in color were assessedaccording to the gray scale.Fastness to rubbingThe dyed polyester fabric placed on the baseof a crock meter, so that it rested flat on theabrasive cloth with its long dimension in thedirection of rubbing. A square of whitetesting cloth forced to slide on the testedfabric back and forth twenty times. For thewet rubbing test, the test square was wettedin distilled water. The rest of the procedurewas the same as the dry test. The staining onthe white testing cloth was assessed usinggray scale.Results and DiscussionSynthesis of some dyes based on 3dimethylamino-1-p-arylpropenones moietyhas been reported (Al-Shiekh, et al., 2008;Hajós, et al., 2008; Almazroa, et al., 2004).Herein, in an attempt to evaluate theirdyeing performance, thus enaminones 3a,breact with phenyl diazonium salt in acidicmedium afforded the disperse dyes 5a,b (Scheme 1).Fastness to lightLight fastness was determined by exposingthe dyed polyester on a Xenotest 150Original Hanau, chamber temperature 25-30 C, black panel temperature 60 C, relativehumidity 50-60%, and dark glass (UV) filtersystem) for 40 h. The changes in color were925

Int.J.Curr.Microbiol.App.Sci (2015) 4(5): 923-928Disperse dyes 5a,b were applied to polyesterfabrics at 2% (shade), using hightemperature dyeing method (HT) at 130 C.Greenish-yellow and yellowish-orangecolour shades were obtained. The dyeingproperties on the polyester fabrics wereevaluated in terms of their fastnessproperties (e.g., fastness to rubbing, washing,perspiration and light). The colour of dyeingon polyester fabrics is expressed in terms ofCIELAB colour space values (Table 1). Thefollowing CIELAB coordinates weremeasured: lightness or darkness (L*);brightness or dullness (chroma (C*)); hueangle (h) from 0 to 360 ; a*, whose valuerepresents the degree of redness (positive)and greenness (negative); and b*, whosevalue represents the degree of yellowness(positive) and blueness (negative). Thesurface colour yield K/S was used to explainthe amount of dye absorbed on the surfaceof the fibre. The K/S values listed in (Table1) show that dyes 5a,b showed high affinityfor the polyester fabrics and the K/S were allgenerally satisfactory. In general, the colorhues of the disperse dye 5a on the polyesterfabric shifted to the greenish directions; thiswas indicated by the negative value of a* 20.37 (red green axis).The fastness ratings are recorded in (Table2), shows that the disperse dyes displayedvery good fastness levels to washing andexcellent fastness levels to both rubbing andperspiration. The light fastness of the dyes5a,b displayed fair fastness on polyesterfabrics. It is of value to mention here thatlight fastness was obtained by the dye 5bcontaining a nitro group in the couplingcomponent, the nitro group increases thepolarity of the dyes (Al-Etaibi et al., 2014a),which may link them more strongly to thefabric and it opens an extra way for thedissipation of energy after light absorptionwhich decreases fading. Attempts are inhand to improve the light fastness propertiesof these dyes. It can be seen from Table 2that the rating nature of substituents on thearomatic moieties of the dye moleculesdetermined the wash fastness for dyedfabrics. Electron-withdrawing group enablestronger Van der Waals forces and hydrogenbonding with the dyed fabrics that increasestheir stability to washing.Table.1 Shade and optical measurements of the azo disperse dyes on the polyester fabricsDyeNoColor shade onpolyesterAbsorption( max b*C*h*K/S77.22 -20.37 53.94 57.66 110.69 17.5967.58 9.29 61.34 62.04 81.39 16.69Table.2 Fastness properties of azo disperse dyes on polyester fabrics *DyeNo5a5bRubbingfastnessDryWet5555Wash fastnessAlt4-54-5SC4-54-5SW3-44Perspiration fastnessLightAlkalineAcidicfastnessAlt SC SW Alt SC SW55555535555553 4* Alt alteration; SC staining on cotton; SW staining on wool926

Int.J.Curr.Microbiol.App.Sci (2015) 4(5): 923-928Table.3 Diameter of the zones of inhibition of the tested disperse dyes against Grampositive, Gram negative bacteria, yeast and fungiDyeNo5a5bInhibition zone diameter (Nearest mm)G Ve bacteriaG-Ve bacteriaYeastB. cereusS. aureusE. coli P. aeruginosa C. albicans111198NI1812101420FungiA. NigerNI24(NI) No Inhibition.Well Diameter: 6 mmScheme.1OH3COCH3 NH3COCH3CH3X1a, X CH3b, X NO22OOHONCH3CH3X PhN N Cl4X3a, X CH3b, X NO2NNH5a, X CH3b, X NO2aldehydes disperse dyes. The dyes producedin this manner were then applied topolyester fabrics by using high temperaturedyeing method at 130 C. The dyed fabricsdisplayed greenish-yellow and yellowishorange on polyester fabric, have fair, verygood and excellent fastness levels to light,washing,rubbingandperspiration,respectively. Finally, the antimicrobialactivities of the synthesized disperse dyesagainst Gram positive bacteria, Gramnegative bacteria, yeast and fungus werediscussed.Antimicrobial activitiesThe inhibition zone diameter data for the 3oxo-2-(phenylhydrazono)-3-parylpropionaldehydes disperse dyes, givenin (Table 3), shows that all of the tested dyesshowed strong positive antimicrobialactivities against at least four of the testedmicroorganisms. Both of disperse dyes 5a,bshowed cytolytic effect even after five dyesof incubation, there were no growthrecorded in the inhibited zone for all of thetested microbes. Comparison betweenconventional and both of microwave,ultrasound dyeing, for these disperse dyesare under investigation.ReferencesAbdou, M. M. 2013. Thiophene-Based AzoDyes and Their Applications in DyesChemistry, Amer. J. Chem., 3(5): nes coupled with phenyldiazonium salt to give the corresponding 3oxo-2-(phenylhydrazono)-3-p-aryl-propion927

Int.J.Curr.Microbiol.App.Sci (2015) 4(5): 923-928Al-Awadi, N. A., Elnagdi, M. H.; Ibrahim, Y.A., Kaul, K., Kumar. 2001. A. Efficientsynthesis of 3-aroylcinnolines from arylmethyl ketones, Tetrahedron, 57, 16091614.Al-Etaibi, A. M.; El-Apasery, M. A.; Ibrahim,M. R., Al-Awadi, N. A. 2012. A facilesynthesis of new monoazo disperse Evaluation of microwave assisteddyeing behavior. Molecules, 17 (12),13891-13909.Al-Etaibi, A., Kamel, M. M., El-Apasery, M.A. 2014a. Synthesis and applications ofnew aminothienopyridazines dispersedyes on polyester fabric. Int. J. Curr.Microbiol. App. Sci, 3 (11), 826-832.Al-Etaibi, A., El-Apasery, M. A., Mahmoud,H., Al-Awadi, N. 2014b. , and applications of new azopyridone disperse dyes on polyesterfabric, Euro. J. Chem., 5 (2), 321-327.Al-Etaibi A.M, Al-Awadi N A., El-Apasery,M A. 2011. Synthesis of Some NovelPyrazolo [1,5-a] pyrimidine Derivativesand Their Application as Disperse Dyes.Molecules, 6: 5182-5193.Almazroa, S., Elnagdi, M. H., Salah El-Din,A. M. 2004. Studies with enaminones:The reaction of enaminones withaminoheterocycles.Aroutetoazolopyrimidines, azolopyridines andquinolines. J. Het. Chem., 41(2), 267272.Al-Mousawi, S. A., El-Apasery, M. A.,Elnagdi, M. H. 2014. Arylazoazines andarylazoazoles as interesting dispersedyes: Recent developments withemphasis on our contribution laboratoryoutcomes, Euro. J. Chem., 5 (1), 192200.Al-Saleh B, El-Apasery M. A., Elnagdi M. H.2004. Studies with 3-substituted 2arylhydrazono-3-oxoaldehydes:newroutes for synthesis of 2 ylpyrazoles and 4-arylazophenols. J.Chem. Res., (S), 8, 578 80.Al-Shiekh, M. A., Medrassi, H. Y., Elnagdi,M. H., Hafez, E. A., 2008, Studies with2-arylhydrazono-3-oxopropanals: routesfor the synthesis of pyridazine-3,4dicarboxylate and 3,5-diaroyl pyrazoles,ARKIVOC, (xvii), 36-47.Chrysler, L. P. 1990. Methods of Test forColour Fastness of Textiles and Leather,7th ed., Bradford, London, pp. 89-94.El-Apasery, M. A., Al-Mousawi, S. M.,Mahmoud, H., Elnagdi, M. H. 2011.Novel routes to biologically activeenaminones, dienoic acid amides,arylazonicotinatesanddihydropyridazines under microwaveirradiation, Int. Res. J. Pure Appl.Chem., 69-83.El-Molla, M. M., Ismaeil, Z. H., Soliman, F.M. A., Abd-El Monem, S. H. 2013.Synthesis of Several Newly DisperseDyes and their Application in TextilePrinting. J. Text. Associat., 18-25.Fadda, A. A., Elattar, K. M. 2013. Efficientand Convenient Route for the Synthesisof Some New Antipyrinyl MonoazoDyes: Application to Polyester Fibersand Biological Evaluation, Journal ofChemistry, ID 928106,Klaus H. 2003. Industrial Dyes, Chemistry,Properties, Applications, Wiley-VCH,Weinheim, 20 35.Vaskó, G. Á., Riedl, Z., Egyed, O., Hajós, G.2008. Synthesis of a new tricylic ringsystem:[1,2,3]triazolo[1,5-b]cinnoliniumsalt, ARKIVOC, (iii) 25-32.Zollinger H. 2003. Color Chemistry,Synthesis, Properties and Applicationsof Organic Dyes and pigments. 3rdrevised ed., Wiley-VCH, Weinheim.928

Dyeing of polyester with disperse dyes: Part 1. Antimicrobial activity and dyeing performance of some disperse dyes Alya Al-Etaibi1*, Morsy Ahmed El-Apasery2 and Magda M. Kamel2 1Natural Science Department, College of Health Science, Public Authority for Applied Education and Training, Fayha, 72853, Kuwait

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