High-molecular weight organic compounds known as carriers are widely used to expedite polyester dyeing at atmospheric pressure at 100 °C. However, carriers are usually poorly biodegradable and can partially plasticize fibres. Also, dyeing at temperatures above 100 °C in the absence of a carrier entails using expensive equipment. In this work, we developed an alternative method for dyeing polyester at temperatures below 100 °C that reduces energy expenses, dispenses with the need to invest in new equipment and avoids the undesirable effects of non-biodegradable carriers. The method uses disperse dyes in a microemulsion containing a low proportion of a non-toxic organic solvent and either of two alternative development auxiliaries (coumarin and o-vanillin) that is prepared with the aid of ultrasoundPostprint (published version

Carrión Fité, Francisco Javier

Radei, Shahram

IOP Conference Series : Materials Science and Engineering

English

UPCommons. Portal del coneixement obert de la UPC

IOP Conference Series: Materials Science and EngineeringPAPER • OPEN ACCESSDevelopment auxiliaries for dyeing polyester withdisperse dyes at low temperaturesTo cite this article: F J Carrion- Fite and S Radei 2017 IOP Conf. Ser.: Mater. Sci. Eng. 254 082006 View the article online for updates and enhancements.Related contentStudy on Glow Discharge Plasma Used inPolyester Surface ModificationLiu Wenzheng, Lei Xiao and Zhao Qiang-Erosive wear characteristics of multi-fiberreinforced polyester under differentoperating conditionsU K Debnath, M A Chowdhury and D MNuruzzaman-Study on moisture absorption and sweatdischarge of honeycomb polyester fiberAifen Feng and Yongjiu Zhang-This content was downloaded from IP address 47.61.226.246 on 11/01/2018 at 17:531Content from this work may be used under the terms of the Creative Commons Attribution 3.0 licence. Any further distributionof this work must maintain attribution to the author(s) and the title of the work, journal citation and DOI.Published under licence by IOP Publishing Ltd123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006Development auxiliaries for dyeing polyester with dispersedyes at low temperaturesF J Carrion- Fite 1 and S Radei11Institute for Textile Research and Industrial Cooperation of Terrassa (INTEXTER)and Department of Materials Science and Metalurgical Engineering (CMEM) Sectionin the field of Textile Engineering (SAET),-Universitat Politecnica deCatalunya,(UPC)- Colom 15, 08222 Terrassa,( Barcelona), SpainEmail: javier.carrion@upc.eduAbstract. High-molecular weight organic compounds known as carriers are widely used toexpedite polyester dyeing at atmospheric pressure at 100 ºC. However, carriers are usuallypoorly biodegradable and can partially plasticize fibres. Also, dyeing at temperatures above100 ºC in the absence of a carrier entails using expensive equipment. In this work, wedeveloped an alternative method for dyeing polyester at temperatures below 100 ºC thatreduces energy expenses, dispenses with the need to invest in new equipment and avoids theundesirable effects of non-biodegradable carriers. The method uses disperse dyes in a micro-emulsion containing a low proportion of a non-toxic organic solvent and either of twoalternative development auxiliaries (coumarin and o-vanillin) that is prepared with the aid ofultrasound.1. IntroductionPET fibres are hydrophobic [1] and contain no chemically active groups, which hinders their dyeing inaqueous media [2] and requires using disperse dyes that are almost insoluble in water [3,4] . In fact,dyeing polyester typically entails dispersing a swelling agent (a carrier) and the dye among fibres at ahigh temperature and pressure [5] Efficiently using disperse dyes with polyester fibres entails operatingat temperatures above their glass transition point (80 ºC) [ 6–8] Some organic solvents used as carriersto swell polyester fibres for dyeing contain phenyl-phenol, phenyl-chloride or phenyl-alkyl groups,among others [ 9–11]´ As noted earlier, carriers are often scarcely biodegradable and tend to plasticizefibres, thereby lowering their glass transition temperature (Tg) [ 12] .Carrión-Fite [7] developed an alternative method for dyeing polyester with reduced energy costs,investments and unwanted effects [13]. The method uses temperatures as low as 40 ºC or even lower incombination with disperse dyes in a micro-emulsion containing a low proportion of an organic solvent(an alkyl halogen) and phosphoglyceride as emulsifier that is prepared under sonication [7].Growing ecological concerns have led to strict regulation of textile dyeing and finishing processes [14],which has promoted a search for natural, safer substances for use by the wet textile processing industry[7, 14, 15]. For example, Pasquet et al [15] used o- and p-vanillin at high concentrations as alternativesfor toxic carriers in the low-temperature dyeing of polyester fabrics with low-molecular weight dispersedyes in the presence of ethanol as co-solvent.In this work, we developed an alternative method for dyeing polyester with disperse dyes at a lowtemperature. The method uses a micro-emulsion consisting of a non-toxic organic co-solvent n-butylacetate, which was previously used by Carrion-Fite [15] and either of two agro-sourced development2123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006auxiliaries[o-vanillin, which was previously employed by Pasquet et al [16], or coumarin. Themicroemulsion is prepared with the aid of ultrasound. The dyeing process was conducted by usingvarious low-molecular weight disperse dyes at different temperatures below 100 ºC and its kinetics ateach temperature examined.2. Experimental2.1. MaterialsFabric. Standard polyester, Type 30 A (Code 30,000), from wfk Testgewebe GmbH (Brüggen,Germany) (ISO 105-F10).Chemicals. The low-molecular weight disperse dyes Rubin Foron E-5R (C.I. Disperse Red 73), andBlue Foron E-BL (C.I. Disperse Blue 56), both supplied by Clariant (Muttenz, Switzerland) (see Figs 1and 2).Figure 1. Structure of C.I. Disperse Red 73 (C.I.11116, CAS 16889104, MW = 348.36 g·mol–1)Figure 2. Structure of (C.I. Disperse Blue 56, C.I.63285, CAS 12217797, MW = 365.18 g·mol–1)Organic solvent. Pure n-butyl acetate (MW = 116.16 g·mol–1) supplied by Panreac (Barcelona, Spain).Auxiliaries. Coumarin 99% pure (MW = 146.15, CAS No. 91-64-5) supplied Acros (New Jersey,USA)and o-vanillin (2-hydroxy-3-methoxybenzaldehyde, MW = 152.15, CAS No. 148-53-8) in 99% puritysupplied by Acros (New Jersey, USA).Figure 3. Chemical structure of coumarin. Figure 4. Chemical structure of o-vanillin.Solvent for extraction of disperse dyes on polyester. N,N-Dimethylformamide for analysis (MW = 73.10g·mol–1) supplied in 99.8% purity by Panreac (Barcelona, Spain).Non-ionic surfactant for pre-dyeing washing. Hostapal, obtained from Archroma GmbH (Sulzbach,Germany).Post-dyeing reductant. QP-grade 85% pure sodium dithionite (MW = 174.11 g·mol–1) and analytical-grade sodium hydroxide purissimum, both supplied by Panreac.2.2. EquipmentDyeing. A Linitest dyeing apparatus furnished with 300 ml sealed cans that was purchased from AtlasMTT GmbH (Germany)Washing. A Launder-Ometer with 550 ml sealed cans also purchased from Atlas (Illinois, USA).Spectrophotometry. A model M 330 UV–Visible spectrophotometer from Camspec, Ltd. (Cambridge,UK).3123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006Sonication. A Labsonic 1510 shaker equipped with a standard probe of 19 mm Ø that was supplied byB. Braun (Hessen, Germany).2.3. Procedures2.3.1 Fabric pre-washing. Cleanliness in the standard polyester fabric used was ensured by washingwith Hostapal detergent at a 0.5 g·L–1 concentration at 40 ºC for 30 min.2.3.2 Dyeing conditions. The dyeing bath contained 3 g of polyester fabric, a 2% concentration ofdisperse dye, a 1 ml/1 g  o.w.f. concentration of solvent (n-butyl acetate) and a 4% o.w.f. concentrationof auxiliary. The bath ratio was 1:60 and the temperature 65, 75, 83 or 95 ºC. The dyeing apparatus wasused with closed containers at a constant agitation rate and temperature. The operation time was 120min —by exception, that used at the lowest temperature (65 ºC) was 150 min.2.3.3 Dyeing procedure. Each dyeing bath was prepared from a 4% o.w.f. concentration of auxiliary (o-vanillin or coumarin) that was dispersed in 3 ml of n-butyl acetate and made to 180 ml (B.R: 1:60) withdistilled water. Emulsification was facilitated by mechanical stirring with a propeller shaker, followedby ultrasound (2 w/ml, 1 min). The auxiliary emulsion contained a 2% o.w.f. concentration of dispersedye —previously dissolved in the solvent— in the required volume for the applicable bath ratio (180ml). Each emulsion was warmed to the present temperature for each assay, which was kept constantthroughout the dyeing process. The temperatures used were 65, 75, 83 and 95 °C. One-half of all testsused o-vanillin and the other half coumarin as auxiliary.2.3.4 Post-dyeing washing. After dyeing, the fabric was washed in a reductive medium to remove alldye absorbed onto fibre surfaces. The reduction washing process consisted of 0.5 g/l soda and 2 g/lsodium hydrosulphite in distilled water and was followed by washing at 50 °C for 30 min. The bath ratiowas 1:50 (150 ml per sample). The equipment used to wash dyed fabric was a Launder-Ometer with 550ml cans for each specimen. An amount of 3 g of specimen was washed in a 150 ml wash bath under theabove-described conditions. After, the wash fastness of a dyed fabrics during 120 min was obtained.2.3.5 Determination dye absorption. The amount of dye absorbed by the polyester fabric was determinedby extraction with N,N-dimethylformamide (DMF) and calculated from a linear line for the calibrationof each disperse dye. As per the Beer–Lambert law, the absorbance at the maximum wavelength in thevisible spectrum was a linear function of the concentration of dye dispersed in DMF.3. Result and discussion3.1 Dyeing kinetics and rate constantFigures 5–8 illustrate the kinetics of dyeing with the two disperse dyes in the presence of the twoauxiliaries used, namely: C.I. Disperse Red 73 with coumarin (Figure. 5), C.I. Disperse Red 73 with o-vanillin (Figure 6), C.I. Disperse Blue 56 with coumarin (Figure. 7) and C.I. Disperse Blue 56 with o-vanillin (Figure. 8).The diffusion of dyes into fibres depends on the local rate of dye transport in the substrate in relation tothe concentration gradient, the geometry of the medium, and the radius of the fibre cross-section. Thedifficulty of measuring these variables led us to use the following Cegarra-Puente kinetic equation [8]:1 − = −K (1)WhereCt = dye concentration on fibres at time tC∞= initial concentration in the dye bath4123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006K = dyeing rate constantt = timeFigure 7 Kinetics of dyeing with C.I. Disperse Blue56 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and coumarin ( 0.666 g·l–1).Figure 8 Kinetics of dyeing with C.I. Disperse Blue56 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and o-vanillin (0.666 g·l–1).Table 1 shows the dyeing absorption rate constants, and their respective correlation coefficients, ascalculated from equation (1).Table 1. Absorption rate constant (K) and correlation coefficient (r) for the kinetics of dyeing ofpolyester with disperse dyes in the presence of o-vanillin or coumarin as development auxiliary.05101520250 50 100 150 200g dye/kg fabrictime (min)65 ªC 75 ºC 83 ºC 95 ªC-505101520250 50 100 150 200g dye/kg fabrictime (min)65 ºC 75 ºC 83 ºC 95 ºCFigure 5 Kinetics of dyeing with C.I. Disperse Red73 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and coumarin (0.666 g·l–1).Figure 6 Kinetics of dyeing with C.I. Disperse Red73 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and o-vanillin (0.666 g·l–1).051015200 50 100 150 200g dye/kg fabrictime (min)95 ºC 83º C 75 ºC 65 ºC051015200 50 100 150 200g dye/kg fabrictime (min)95 ºC 83 ºC 75 ºC 65 ºC5123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006Auxiliary agent:  o Vanillin Auxiliary agent:  CoumarinDisperse dyes RateconstantCorrelationcoefficientExhaustion %after 120 minRateconstantCorrelationcoefficientExhaustion %after120 minC.I. DisperseRed  73 at 95ºC 0.0073 0.9476 81.68 0.0078 0.8953 82.26I. Disperse  Red73 at 83 ºC 0.0054 0.9672 69.88 0.0052 0.9491 71.06C.I. DisperseRed  73 at75 ºC 0.0037 0.9723 61.47 0.0027 0.7989 55.84C.I. DisperseRed  73 at 65 ºC 0.0017 0.9568 48.53 0.0011 0.88 39.76C.I. DisperseBlue 56 at 95ºC 0.0221 0.9874 97.51 0.0183 0.912 96.31C.I. DisperseBlue 56 at 83 ºC 0.0155 0.9316 93.85 0.0116 0.9355 90.81C.I. DisperseBlue 56 at75 ºC 0.085 0.9455 83.32 0.0035 0.9358 61.62C.I. DisperseBlue 56 at65 ºC 0.0027 0.8154 58.43 0.002 0.9437 55.06As can be seen, the absorption rate constant for both dyes increased with increasing temperature. Also,the correlation coefficients were good (in general, higher than 0.94 with o-vanillin and somewhat lowerbut still exceeding, in general, 0.91 with coumarin). Exhaustion after dyeing was acceptable in all casesexcept below 75 ºC — this temperature is lower than glass transition temperature of polyester.3.2 Wash fastness of polyester fabric dyedTable 2 shows colour fastness of to domestic and commercial laundering according to the standardmethodology and using the A2S test indicated in this standard [17].Table 2 Colour fastness of the polyester dyedGenerally, in respect to Table 2 dyed fabric the washing fastness is acceptable for all samples and theirvalues are quite similar for both dyes and slightly better in coumarin than o-vanillin agent. Staining ofPET fabric dyed 120 minutesAuxiliary : O_Vanillin Auxiliary : CoumarinGrayScalePET Cotton GrayScalePET CottonC.I. Disperse  Red  73 at 65ºC 2 3 3 3-4 3-4 3C.I. Disperse  Red  73 at 75 ºC 3 3 3 4-5 3-4 3-4C.I. Disperse  Red  73 at  83 ºC 4 3 4 3 4 4-5C.I. Disperse  Red  73 at  95 ºC 4-5 4 4-5 5 4-5 4C.I. Disperse  Blue 56 at 65 ºC 2-3 3 2-3 3 3 2-3C.I. Disperse  Blue 56 at 75 ºC 4-5 3 3 4 3-4 2-3C.I. Disperse  Blue 56 at 83  ºC 4-5 4 3 3 4 3-4C.I. Disperse Blue 56 at 95 ºC 4 4-5 3-4 4 4-5 46123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006the white polyester fabric is regular for all dyes and auxiliaries tested. In respect to the white cottonfabric values are almost similar and shows the regular level.4. ConclusionsThis paper reports a new method for dyeing polyester fabric with disperse dyes at temperatures below100ºC. The dyes are dispersed in a small volume of n-butyl acetate to obtain a micro-emulsion to whicha development auxiliary (coumarin or o-vanillin) is added. The low molecular weight disperse dyes usedexhibited acceptable exhaustion after 120 minutes and gray scale values of washing fastness was slightlybetter than o-vanillin. The absorption rate constants values increases with increasing temperature.References[1] EU Regulation 1007/2011 of the European Parliament and of the Council of 27 September 2011.Ref. 2011R1007 – EN – 21.12.2011 – 001.001 – p20.[2] Bird C L and Boston W S, Editor 1975 .The Theory of Coloration of Textiles, Dyers CompanyPublications Trust, Bradford, U.K.[3] Datyner A 1978 . The Solubilization of Disperse Dyes by Dispersing Agents at 127 ºC. J. Soc. DyersColour 94, 256.[4] Weingarten R 1979 Theoretische Betrachtungen über das Fárben von Polyesterfasern mitDispersionsfarbstoffen und ihre Bedeutung für die Praxis, Textil Prax. Int. 28, 231, 340[5] Vigo T L 1994. Textile Processing and Properties, Preparation, Dyeing, Finishing andPerformance, Elsevier Science B.V. Amsterdam (The Netherlands)[6] Cegarra J, Carrion F J, Puente P and Valldeperas J 1984 . Kinetik des Färbens modifizierterPolyesterfarsen mit Kationischen Frbsstoffen (Kinetics of Dyeing Modified Polyester Fibres withCationic Dyes). Melliand Textilberichte, 4, 405.[7] Carrion Fite F J 1995. Dyeing of Polyester at Low Temperature: Kinetics of Dyeing with   Disperse Dyes,Textile Research Journal, 65, (6) ,362[8] Cegarra J, Puente P and Carrion F J 1982 , Empirical Equations of Dyeing Kinetics, Textile Res.J., 52(3), 193[9] Nunn D M 1979. The dyeing of synthetic- polymer and acetate fibres. England: Dyers CompanyPublications Trust, Bradford, West Yorkshire (UK), distributed by Society of Dyers andColourists.[10]   Arcoria, A, Cerniani A, De Giorgi R., Longo M , Toscanoa R 1989. Carrier dyeing of polyesterfibre with some disperse Azo dyes, Dyes Pigm., 11, 269–76.[11] Arcoria A, Longo M L Parisi, G 1985, Effects of the phenol on the dyeing of polyester fibre withsome disperse Azo-dyes, Dyes Pigm., 6, 155[12] Peters R.H. Textile Chemistry 2, vol. III 1975. Elsevier, Amsterdam (The Netherlands).[13] Weingarten R 1979 , Theoretische Betrachtungen über das Fárben von Polyesterfasern mitDispersionsfarbstoffen und ihre Bedeutung für die Praxis, Textil Prax. Int, 28, 231, 340, 397.[14] Choudhury A K R 2006. Textile preparation and dyeing, Enfield, N.H. Science: Plymouth;NBN(distributor) USA,[15] Carrion F J 2016. Dyeing polyester at low temperature with disperse dyes and ecological auxiliaries,Proceedings XXIV International Congress, poster 13, Prague (Czech Republic).[16] Pasquet V, Perwuelz A, Behary N, Isaad, J 2013. Vanillin, a potential carrier for low temperaturedyeing of polyester fabrics. Journal of Cleaner Production, 43,:20[17] Textiles. Test for colour fastness. 2010 Part C06: Colour fastness to domestic and commerciallaundering (ISO 105-C06:2010), adapted to Spanish by UNE-EN ISO 105-C06

Development auxiliaries for dyeing polyester with disperse dyes at low temperatures

UPCommons (Universitat Politècnica de Catalunya)

IOP Conference Series: Materials Science and EngineeringPAPER • OPEN ACCESSDevelopment auxiliaries for dyeing polyester withdisperse dyes at low temperaturesTo cite this article: F J Carrion- Fite and S Radei 2017 IOP Conf. Ser.: Mater. Sci. Eng. 254 082006 View the article online for updates and enhancements.Related contentStudy on Glow Discharge Plasma Used inPolyester Surface ModificationLiu Wenzheng, Lei Xiao and Zhao Qiang-Erosive wear characteristics of multi-fiberreinforced polyester under differentoperating conditionsU K Debnath, M A Chowdhury and D MNuruzzaman-Study on moisture absorption and sweatdischarge of honeycomb polyester fiberAifen Feng and Yongjiu Zhang-This content was downloaded from IP address 47.61.226.246 on 11/01/2018 at 17:531Content from this work may be used under the terms of the Creative Commons Attribution 3.0 licence. Any further distributionof this work must maintain attribution to the author(s) and the title of the work, journal citation and DOI.Published under licence by IOP Publishing Ltd123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006Development auxiliaries for dyeing polyester with dispersedyes at low temperaturesF J Carrion- Fite 1 and S Radei11Institute for Textile Research and Industrial Cooperation of Terrassa (INTEXTER)and Department of Materials Science and Metalurgical Engineering (CMEM) Sectionin the field of Textile Engineering (SAET),-Universitat Politecnica deCatalunya,(UPC)- Colom 15, 08222 Terrassa,( Barcelona), SpainEmail: javier.carrion@upc.eduAbstract. High-molecular weight organic compounds known as carriers are widely used toexpedite polyester dyeing at atmospheric pressure at 100 ºC. However, carriers are usuallypoorly biodegradable and can partially plasticize fibres. Also, dyeing at temperatures above100 ºC in the absence of a carrier entails using expensive equipment. In this work, wedeveloped an alternative method for dyeing polyester at temperatures below 100 ºC thatreduces energy expenses, dispenses with the need to invest in new equipment and avoids theundesirable effects of non-biodegradable carriers. The method uses disperse dyes in a micro-emulsion containing a low proportion of a non-toxic organic solvent and either of twoalternative development auxiliaries (coumarin and o-vanillin) that is prepared with the aid ofultrasound.1. IntroductionPET fibres are hydrophobic [1] and contain no chemically active groups, which hinders their dyeing inaqueous media [2] and requires using disperse dyes that are almost insoluble in water [3,4] . In fact,dyeing polyester typically entails dispersing a swelling agent (a carrier) and the dye among fibres at ahigh temperature and pressure [5] Efficiently using disperse dyes with polyester fibres entails operatingat temperatures above their glass transition point (80 ºC) [ 6–8] Some organic solvents used as carriersto swell polyester fibres for dyeing contain phenyl-phenol, phenyl-chloride or phenyl-alkyl groups,among others [ 9–11]´ As noted earlier, carriers are often scarcely biodegradable and tend to plasticizefibres, thereby lowering their glass transition temperature (Tg) [ 12] .Carrión-Fite [7] developed an alternative method for dyeing polyester with reduced energy costs,investments and unwanted effects [13]. The method uses temperatures as low as 40 ºC or even lower incombination with disperse dyes in a micro-emulsion containing a low proportion of an organic solvent(an alkyl halogen) and phosphoglyceride as emulsifier that is prepared under sonication [7].Growing ecological concerns have led to strict regulation of textile dyeing and finishing processes [14],which has promoted a search for natural, safer substances for use by the wet textile processing industry[7, 14, 15]. For example, Pasquet et al [15] used o- and p-vanillin at high concentrations as alternativesfor toxic carriers in the low-temperature dyeing of polyester fabrics with low-molecular weight dispersedyes in the presence of ethanol as co-solvent.In this work, we developed an alternative method for dyeing polyester with disperse dyes at a lowtemperature. The method uses a micro-emulsion consisting of a non-toxic organic co-solvent n-butylacetate, which was previously used by Carrion-Fite [15] and either of two agro-sourced development2123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006auxiliaries[o-vanillin, which was previously employed by Pasquet et al [16], or coumarin. Themicroemulsion is prepared with the aid of ultrasound. The dyeing process was conducted by usingvarious low-molecular weight disperse dyes at different temperatures below 100 ºC and its kinetics ateach temperature examined.2. Experimental2.1. MaterialsFabric. Standard polyester, Type 30 A (Code 30,000), from wfk Testgewebe GmbH (Brüggen,Germany) (ISO 105-F10).Chemicals. The low-molecular weight disperse dyes Rubin Foron E-5R (C.I. Disperse Red 73), andBlue Foron E-BL (C.I. Disperse Blue 56), both supplied by Clariant (Muttenz, Switzerland) (see Figs 1and 2).Figure 1. Structure of C.I. Disperse Red 73 (C.I.11116, CAS 16889104, MW = 348.36 g·mol–1)Figure 2. Structure of (C.I. Disperse Blue 56, C.I.63285, CAS 12217797, MW = 365.18 g·mol–1)Organic solvent. Pure n-butyl acetate (MW = 116.16 g·mol–1) supplied by Panreac (Barcelona, Spain).Auxiliaries. Coumarin 99% pure (MW = 146.15, CAS No. 91-64-5) supplied Acros (New Jersey,USA)and o-vanillin (2-hydroxy-3-methoxybenzaldehyde, MW = 152.15, CAS No. 148-53-8) in 99% puritysupplied by Acros (New Jersey, USA).Figure 3. Chemical structure of coumarin. Figure 4. Chemical structure of o-vanillin.Solvent for extraction of disperse dyes on polyester. N,N-Dimethylformamide for analysis (MW = 73.10g·mol–1) supplied in 99.8% purity by Panreac (Barcelona, Spain).Non-ionic surfactant for pre-dyeing washing. Hostapal, obtained from Archroma GmbH (Sulzbach,Germany).Post-dyeing reductant. QP-grade 85% pure sodium dithionite (MW = 174.11 g·mol–1) and analytical-grade sodium hydroxide purissimum, both supplied by Panreac.2.2. EquipmentDyeing. A Linitest dyeing apparatus furnished with 300 ml sealed cans that was purchased from AtlasMTT GmbH (Germany)Washing. A Launder-Ometer with 550 ml sealed cans also purchased from Atlas (Illinois, USA).Spectrophotometry. A model M 330 UV–Visible spectrophotometer from Camspec, Ltd. (Cambridge,UK).3123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006Sonication. A Labsonic 1510 shaker equipped with a standard probe of 19 mm Ø that was supplied byB. Braun (Hessen, Germany).2.3. Procedures2.3.1 Fabric pre-washing. Cleanliness in the standard polyester fabric used was ensured by washingwith Hostapal detergent at a 0.5 g·L–1 concentration at 40 ºC for 30 min.2.3.2 Dyeing conditions. The dyeing bath contained 3 g of polyester fabric, a 2% concentration ofdisperse dye, a 1 ml/1 g  o.w.f. concentration of solvent (n-butyl acetate) and a 4% o.w.f. concentrationof auxiliary. The bath ratio was 1:60 and the temperature 65, 75, 83 or 95 ºC. The dyeing apparatus wasused with closed containers at a constant agitation rate and temperature. The operation time was 120min —by exception, that used at the lowest temperature (65 ºC) was 150 min.2.3.3 Dyeing procedure. Each dyeing bath was prepared from a 4% o.w.f. concentration of auxiliary (o-vanillin or coumarin) that was dispersed in 3 ml of n-butyl acetate and made to 180 ml (B.R: 1:60) withdistilled water. Emulsification was facilitated by mechanical stirring with a propeller shaker, followedby ultrasound (2 w/ml, 1 min). The auxiliary emulsion contained a 2% o.w.f. concentration of dispersedye —previously dissolved in the solvent— in the required volume for the applicable bath ratio (180ml). Each emulsion was warmed to the present temperature for each assay, which was kept constantthroughout the dyeing process. The temperatures used were 65, 75, 83 and 95 °C. One-half of all testsused o-vanillin and the other half coumarin as auxiliary.2.3.4 Post-dyeing washing. After dyeing, the fabric was washed in a reductive medium to remove alldye absorbed onto fibre surfaces. The reduction washing process consisted of 0.5 g/l soda and 2 g/lsodium hydrosulphite in distilled water and was followed by washing at 50 °C for 30 min. The bath ratiowas 1:50 (150 ml per sample). The equipment used to wash dyed fabric was a Launder-Ometer with 550ml cans for each specimen. An amount of 3 g of specimen was washed in a 150 ml wash bath under theabove-described conditions. After, the wash fastness of a dyed fabrics during 120 min was obtained.2.3.5 Determination dye absorption. The amount of dye absorbed by the polyester fabric was determinedby extraction with N,N-dimethylformamide (DMF) and calculated from a linear line for the calibrationof each disperse dye. As per the Beer–Lambert law, the absorbance at the maximum wavelength in thevisible spectrum was a linear function of the concentration of dye dispersed in DMF.3. Result and discussion3.1 Dyeing kinetics and rate constantFigures 5–8 illustrate the kinetics of dyeing with the two disperse dyes in the presence of the twoauxiliaries used, namely: C.I. Disperse Red 73 with coumarin (Figure. 5), C.I. Disperse Red 73 with o-vanillin (Figure 6), C.I. Disperse Blue 56 with coumarin (Figure. 7) and C.I. Disperse Blue 56 with o-vanillin (Figure. 8).The diffusion of dyes into fibres depends on the local rate of dye transport in the substrate in relation tothe concentration gradient, the geometry of the medium, and the radius of the fibre cross-section. Thedifficulty of measuring these variables led us to use the following Cegarra-Puente kinetic equation [8]:1 − = −K (1)WhereCt = dye concentration on fibres at time tC∞ = initial concentration in the dye bath4123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006K = dyeing rate constantt = timeFigure 7 Kinetics of dyeing with C.I. Disperse Blue56 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and coumarin ( 0.666 g·l–1).Figure 8 Kinetics of dyeing with C.I. Disperse Blue56 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and o-vanillin (0.666 g·l–1).Table 1 shows the dyeing absorption rate constants, and their respective correlation coefficients, ascalculated from equation (1).Table 1. Absorption rate constant (K) and correlation coefficient (r) for the kinetics of dyeing ofpolyester with disperse dyes in the presence of o-vanillin or coumarin as development auxiliary.05101520250 50 100 150 200g dye/kg fabrictime (min)65 ªC 75 ºC 83 ºC 95 ªC-505101520250 50 100 150 200g dye/kg fabrictime (min)65 ºC 75 ºC 83 ºC 95 ºCFigure 5 Kinetics of dyeing with C.I. Disperse Red73 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and coumarin (0.666 g·l–1).Figure 6 Kinetics of dyeing with C.I. Disperse Red73 absorbed by polyester fabric at differenttemperatures in the presence of butyl acetate (16.666g·l–1) and o-vanillin (0.666 g·l–1).051015200 50 100 150 200g dye/kg fabrictime (min)95 ºC 83º C 75 ºC 65 ºC051015200 50 100 150 200g dye/kg fabrictime (min)95 ºC 83 ºC 75 ºC 65 ºC5123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006Auxiliary agent:  o Vanillin Auxiliary agent:  CoumarinDisperse dyes RateconstantCorrelationcoefficientExhaustion %after 120 minRateconstantCorrelationcoefficientExhaustion %after120 minC.I. DisperseRed  73 at 95ºC 0.0073 0.9476 81.68 0.0078 0.8953 82.26I. Disperse  Red73 at 83 ºC 0.0054 0.9672 69.88 0.0052 0.9491 71.06C.I. DisperseRed  73 at75 ºC 0.0037 0.9723 61.47 0.0027 0.7989 55.84C.I. DisperseRed  73 at 65 ºC 0.0017 0.9568 48.53 0.0011 0.88 39.76C.I. DisperseBlue 56 at 95ºC 0.0221 0.9874 97.51 0.0183 0.912 96.31C.I. DisperseBlue 56 at 83 ºC 0.0155 0.9316 93.85 0.0116 0.9355 90.81C.I. DisperseBlue 56 at75 ºC 0.085 0.9455 83.32 0.0035 0.9358 61.62C.I. DisperseBlue 56 at65 ºC 0.0027 0.8154 58.43 0.002 0.9437 55.06As can be seen, the absorption rate constant for both dyes increased with increasing temperature. Also,the correlation coefficients were good (in general, higher than 0.94 with o-vanillin and somewhat lowerbut still exceeding, in general, 0.91 with coumarin). Exhaustion after dyeing was acceptable in all casesexcept below 75 ºC — this temperature is lower than glass transition temperature of polyester.3.2 Wash fastness of polyester fabric dyedTable 2 shows colour fastness of to domestic and commercial laundering according to the standardmethodology and using the A2S test indicated in this standard [17].Table 2 Colour fastness of the polyester dyedGenerally, in respect to Table 2 dyed fabric the washing fastness is acceptable for all samples and theirvalues are quite similar for both dyes and slightly better in coumarin than o-vanillin agent. Staining ofPET fabric dyed 120 minutesAuxiliary : O_Vanillin Auxiliary : CoumarinGrayScalePET Cotton GrayScalePET CottonC.I. Disperse  Red  73 at 65ºC 2 3 3 3-4 3-4 3C.I. Disperse  Red  73 at 75 ºC 3 3 3 4-5 3-4 3-4C.I. Disperse  Red  73 at  83 ºC 4 3 4 3 4 4-5C.I. Disperse  Red  73 at  95 ºC 4-5 4 4-5 5 4-5 4C.I. Disperse  Blue 56 at 65 ºC 2-3 3 2-3 3 3 2-3C.I. Disperse  Blue 56 at 75 ºC 4-5 3 3 4 3-4 2-3C.I. Disperse  Blue 56 at 83  ºC 4-5 4 3 3 4 3-4C.I. Disperse Blue 56 at 95 ºC 4 4-5 3-4 4 4-5 46123456789017th World Textile Conference AUTEX 2017- Textiles - Shaping the Future IOP PublishingIOP Conf. Series: Materials Science and Engineering 254 (2017) 082006 doi:10.1088/1757-899X/254/8/082006the white polyester fabric is regular for all dyes and auxiliaries tested. In respect to the white cottonfabric values are almost similar and shows the regular level.4. ConclusionsThis paper reports a new method for dyeing polyester fabric with disperse dyes at temperatures below100ºC. The dyes are dispersed in a small volume of n-butyl acetate to obtain a micro-emulsion to whicha development auxiliary (coumarin or o-vanillin) is added. The low molecular weight disperse dyes usedexhibited acceptable exhaustion after 120 minutes and gray scale values of washing fastness was slightlybetter than o-vanillin. The absorption rate constants values increases with increasing temperature.References[1] EU Regulation 1007/2011 of the European Parliament and of the Council of 27 September 2011.Ref. 2011R1007 – EN – 21.12.2011 – 001.001 – p20.[2] Bird C L and Boston W S, Editor 1975 .The Theory of Coloration of Textiles, Dyers CompanyPublications Trust, Bradford, U.K.[3] Datyner A 1978 . The Solubilization of Disperse Dyes by Dispersing Agents at 127 ºC. J. Soc. DyersColour 94, 256.[4] Weingarten R 1979 Theoretische Betrachtungen über das Fárben von Polyesterfasern mitDispersionsfarbstoffen und ihre Bedeutung für die Praxis, Textil Prax. Int. 28, 231, 340[5] Vigo T L 1994. Textile Processing and Properties, Preparation, Dyeing, Finishing andPerformance, Elsevier Science B.V. Amsterdam (The Netherlands)[6] Cegarra J, Carrion F J, Puente P and Valldeperas J 1984 . Kinetik des Färbens modifizierterPolyesterfarsen mit Kationischen Frbsstoffen (Kinetics of Dyeing Modified Polyester Fibres withCationic Dyes). Melliand Textilberichte, 4, 405.[7] Carrion Fite F J 1995. Dyeing of Polyester at Low Temperature: Kinetics of Dyeing with   Disperse Dyes,Textile Research Journal, 65, (6) ,362[8] Cegarra J, Puente P and Carrion F J 1982 , Empirical Equations of Dyeing Kinetics, Textile Res.J., 52(3), 193[9] Nunn D M 1979. The dyeing of synthetic- polymer and acetate fibres. England: Dyers CompanyPublications Trust, Bradford, West Yorkshire (UK), distributed by Society of Dyers andColourists.[10]   Arcoria, A, Cerniani A, De Giorgi R., Longo M , Toscanoa R 1989. Carrier dyeing of polyesterfibre with some disperse Azo dyes, Dyes Pigm., 11, 269–76.[11] Arcoria A, Longo M L Parisi, G 1985, Effects of the phenol on the dyeing of polyester fibre withsome disperse Azo-dyes, Dyes Pigm., 6, 155[12] Peters R.H. Textile Chemistry 2, vol. III 1975. Elsevier, Amsterdam (The Netherlands).[13] Weingarten R 1979 , Theoretische Betrachtungen über das Fárben von Polyesterfasern mitDispersionsfarbstoffen und ihre Bedeutung für die Praxis, Textil Prax. Int, 28, 231, 340, 397.[14] Choudhury A K R 2006. Textile preparation and dyeing, Enfield, N.H. Science: Plymouth;NBN(distributor) USA,[15] Carrion F J 2016. Dyeing polyester at low temperature with disperse dyes and ecological auxiliaries,Proceedings XXIV International Congress, poster 13, Prague (Czech Republic).[16] Pasquet V, Perwuelz A, Behary N, Isaad, J 2013. Vanillin, a potential carrier for low temperaturedyeing of polyester fabrics. Journal of Cleaner Production, 43,:20[17] Textiles. Test for colour fastness. 2010 Part C06: Colour fastness to domestic and commerciallaundering (ISO 105-C06:2010), adapted to Spanish by UNE-EN ISO 105-C06

High-molecular weight organic compounds known as carriers are widely used to expedite polyester dyeing at atmospheric pressure at 100 °C. However, carriers are usually poorly biodegradable and can partially plasticize fibres. Also, dyeing at temperatures above 100 °C in the absence of a carrier entails using expensive equipment. In this work, we developed an alternative method for dyeing polyester at temperatures below 100 °C that reduces energy expenses, dispenses with the need to invest in new equipment and avoids the undesirable effects of non-biodegradable carriers. The method uses disperse dyes in a microemulsion containing a low proportion of a non-toxic organic solvent and either of two alternative development auxiliaries (coumarin and o-vanillin) that is prepared with the aid of ultrasoun

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IOP Conference Series Materials Science and Engineering

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Development auxiliaries for dyeing polyester with disperse dyes at low temperatures

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