Development of Textile Dyeing Using the Green Supercritical Fluid Technology: a Review

Home , Anthraquinone, Solvent dye

https://doi.org/10.33263/Materials23.373390

ISSN: 2668-5728 https://materials.international

Volume 2, Issue 3, Pages 0373-0390 2020

Received: 9.06.2020

Accepted: 2.09.2020

Review Published: 10.09.2020

Development of Textile Dyeing Using the

Green Supercritical Fluid Technology: A Review

Tarek Abou Elmaaty* 1 , Abdallah Mousa 2 , Hatem Gaafar 2 , Ali Hebeish 2 , Heba Sorour 1 1 Department of Textile Printing, Dyeing & Finishing, Faculty of Applied Arts, Damietta University, Damietta 34512, Damietta, Egypt 2 Department of Textile Printing, Dyeing & auxiliaries, National research center, Cairo, Egypt * Correspondence: [email protected]; Scopus ID: 6603460941

Abstract: Recently, a green supercritical carbon dioxide dyeing process with zero waste-water emission is a hot topic. This review gives light on advances in recent years, including solubilities of different dyes in the supercritical solvent as well as most recent reports about the dyeing of synthetic and natural fibers under supercritical carbon dioxide medium.

Keywords: supercritical carbon dioxide; solubility; synthetic fibers; natural fibers; dyes. © 2020 by the authors. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

1. Introduction

Supercritical carbon dioxide (scCO2) is an eco- disposal in the water streamlet [6,7]. Textile wet friendly solvent known for its potentiality as a processing can outstandingly get an advantage from replacement for aqueous textile wet processing, the utilization of scCO2 as a dyeing medium. scCO2 mainly dyeing [1-4]. A supercritical fluid is a matter has lower mass transfer resistance and higher in a closed system above its critical temperature and diffusion rates than water. This property makes the pressure. It is difficult to determine the borderline dye penetrates much faster into the fibers, leading between the liquid and gaseous state. This state of to slower reaction times. Besides, water-free dyeing matter is known as a supercritical state. Although does not require drying and consequently saving several substances are useful as supercritical fluids, energy. Moreover, the absence of water prevents carbon dioxide has been the most extensively dye hydrolysis, which is a significant problem in utilized [5]. traditional dyeing. In the textile industry, traditional textile wet In scCO2, the wanted color shade is achieved processing utilizes a vast volume of freshwater. This with a small concentration of the dyestuff. Also, the copious water is given away as effluent unreacted dyestuff, as well as CO2, are recycled, contaminated with unreacted dyes and auxiliary leading to cost-effective and green methodology [8]. chemicals. A remarkable share of the money is spent eliminating this waste-water before the

MATERIALS INTERNATIONAL | https://materials.international | 373 Cite This Article: Sorour, H.; Elmaaty, T.A.; Mousa, A.; Gaafar, H.; Hebeish, A. Development of textile dyeing using the green supercritical fluid technology: A Review. Mat Int 2020, 3, 0373-0390. https://doi.org/10.33263/Materials23.373390 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • •

2. What is Supercritical Fluid? The supercritical state is known as the fourth happens since an increment in density diminishes state of matter. A supercritical liquid is characterized mean “intermolecular distance,” expanding the as “a substance over its critical temperature and number of interactions between the solvent and pressure”. At these conditions, the liquid has solute [2,9]. interesting properties. It does not condense or evaporate to create a fluid or a gas. Figure 1 revealed that the supercritical state exists at temperature and pressure conditions over the so-called “critical point”. As the “critical point” of a substance is drawn closer, its isothermal compressibility tends to limitlessness. Consequently, the particular volume or thickness of the substance changes drastically. Within the “critical region”, a substance that’s a gas at standard conditions shows liquid-like density and Figure 1. Pressure-temperature diagram. a much-increased “solvent capacity”. This conduct

3. Supercritical carbon dioxide dyeing apparatus A photograph of three types of supercritical carbon dioxide machines is shown in Figure 2. (a) Figure 2a shows the lab-scale dyeing apparatus located in SCF lab in Damietta UNIVERSITY, Egypt, Figure 2 b shows the pilot-scale machine installed in UNIVERSITY OF Fukui, Japan, and Figure 2c shows the industrial-scale machine of Dycoo, Netherland. The dyeing system includes a cylinder for storing carbon dioxide CO2, a cylinder connected to a pump and regulator. The pump and regulator (b) consist of pump CO2 into and out of the temperature/ pressure vessel. A heating apparatus configured to heat the temperature/pressure vessel's contents according to signals received from a temperature controller [10].

(c)

Figure 2. Photograph of supercritical carbon dioxide apparatuses. (a) Lab-scale supercritical carbon dioxide dyeing equipment, b) pilot-scale ScCO2 dyeing equipment (SCF lab, University of Fukui, Japan) (c) Industrial ScCO2 dyeing equipment (Dycoo, Netherland).

4. The solubility of dyes in supercritical fluid Supercritical dyeing requires studies of phase up the system temperature and pressure optimally. equilibrium between dyes and the supercritical Since the beginning of the supercritical technology, solvent. Dye solubility data is one of the most the solubility of substances in supercritical fluids crucial factors for selecting the dyestuff and setting MATERIALS INTERNATIONAL | https://materials.international| 374 Development of textile dyeing using the green supercritical fluid technology: A Review • • • (SCF) has been determined in detail, and several dimethyl-9,10-anthraquinone (Q4)”. They articles reported on solubility [11,12]. estimated the solubility of dyes under investigation The correlation results between the calculated in a large scope of temperature and pressure. They and experimental solubility were estimated with reported on the phenomena that, at constant system three density-based models: (a) “Chrastil, Bartle; (b) temperature, the increase of pressure causes a Mendez-Santiago–Teja models” (c) “Ziger–Eckert” significant increase in solubility of dyes “Q1-Q4”. semi-empirical correlation.[13-15]. Also, using two On the other hand, increasing system temperature “cubic equation-of-state (EOS) models, namely the resulted in a decrease in CO2 density. The order of “Peng–Robinson EOS (PR-EOS) and the Soave– solubility of the dyes understudy is “Q3 > Q1 > Q2 Redlich–Kwong EOS (SRK-EOS)”. [16,17]. This >> Q4” respectively [20]. section will cover the most important reports that investigated the solubilities of different dyes in ScCO2. Skerget et al. presented a review article discussing solubility data generated from different substances in sub- and supercritical fluids. They organized their study utilizing tables as a form besides the ranges of temperature and pressure. Figure 4. Structures of aminoanthraquinone They also screened the different correlation derivatives. methods experimented in the reports for data modeling. They arranged the compounds into Bae et al. studied the effect of adding a solvent classes based on their chemical behavior “inorganic, to the dye on the solubility in scCO2. The results organometallic, aromatic, nonaromatic organic, indicated that the solubility of non-volatile solid in polymer”. Most of the applications favored the ternary system, inclusive of co-solvent, is correlated very well with the liquid model. They “ScCO2” as a medium [18]. 4.1. The solubility of disperse dyes. agreed that solubility of non-volatile solutes such as 4.1.1. Solubility of anthraquinone disperse dyes. “CI disperses red 60” (Figure 5), “phenanthrene, Many studies reported on the solubility of fluorene and acridine” in SCF at different pressure, anthraquinone disperse dyes in “scCO_2” and temperature, and co-solvent concentration can be estimated the solubility using dynamic and static determined by the liquid model without critical processes. characteristics and solute vapor pressure [21]. For example, Kautz et al. measured the solubility of “1, 4-bis-(n-alkylamino)-9,10- anthraquinones” (Figure 3) in scCO_2 at different ranges of system pressure and temperature Figure 5. Disperse red 60. employing a “flow method”. They also investigated the effect of many C-atoms in alkyl-chain and Shamsipur et al. estimated the solubility of “ solubility of dyestuff, showing a maximum for 9,10-anthraquinone derivatives “(Figure 6), in phenyl-derivative [19]. ScCO2 at different temperatures and pressures employing an easy static method. They correlated the experimental data with the “Peng–Robinson equation of state (PR-EOS)” [22].

Figure 3. “ 1,4- bis- (n- alkylamino)- 9,10- anthraquinones”.

Utilizing an easy static technique, Shamsipur et al. studied the solubility of four “anthraquinone disperse dyes” in ScCO2. Figure 4 shows the structure of those dyes that are mainly “ 1-amino-2- Figure 6. Structures of 9,10-anthraquinone derivative. methyl-9,10-anthraquinone (Q1), 1-amino-2-ethyl- Bao et al. measured the solubility of “C. I. 9,10-anthraquinone (Q2), 1-amino-2,3-dimethyl- disperse red 60” (Figure 5) in scCO_2 at various 9,10-anthraquinone (Q3), and 1-amino-2,4- MATERIALS INTERNATIONAL | https://materials.international | 375 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • • temperatures and pressures utilizing the “batch method” as an alternative to the “flow method” reducing the time required for complete equilibrium, which was estimated as 90 min. At a constant temperature, increasing pressure improved the solubility. They dyed polyester fabrics under Figure 9. Chemical structure of “ (a) CI. Disperse ScCO2 to study the relationship between dye uptake Violet 1, (b) C.I. Disperse Blue 5”. on the fiber and dye solubility. The result proved that polyester fiber's dye uptake increased up to 20 Coelho et al. adduced the solubility of some MPa but dropped after this value [23]. disperse dyes mainly, “(quinizarin) 1,4- Gordillo et al. investigated the solubility of dihydroxyanthraquinone, (disperse red 9) 1- “disperse Blue 14” (Figure 7) using ScCO2 at methylaminoanthraquinone, and (disperse blue 14) different pressures and temperatures. They 1,4-bismethylaminoanthraquinone” (Figure 10) in correlated the solubility values by utilizing an ScCO2 at different pressures and temperatures. An accurate thermodynamically model correlated to acceptable solubility correlation under ScCO2 state equations. Using correlated methods of medium was recorded [28]. different groups, they estimated the solid's critical parameters and physical properties [24].

Figure 7. CI. Disperse Blue 14.

Shamsipur et al. studied the solubility of seven derivatives of “1-hydroxy- 9,10-anthraquinone (AQ1–AQ7)” (Figure 8) under supercritical Figure 10. Chemical structure of “(a) quininzarin, (b) medium at different ranges of pressures and disperse red 9, and (c) disperse blue 14 dyes.” temperatures. An acceptable solubility correlation Also, Alwi et al. investigated the solubility of under the ScCO2 medium was recorded [25]. “1,4-diamino-2,3- dichloro anthraquinone (CI Disperse Violet 28), 1,8-dihydroxy-4,5- dinitro anthraquinone” (Figure 11) in scCO2 at different pressures and temperatures rang utilizing a “flow- type apparatus”. “CI Disperse Violet 28” gave a better result than “1,8-dihydroxy-4,5- dinitroanthraquinone”. Also, a better solubility was recorded upon the addition of “2, 3-dichloro group” to “1, 4-diaminoanthraquione”. The results indicated that the experimental solubility values of the dyestuffs concur with that of the calculated ones utilizing the empirical equations of “Mendez- Figure 8. Structure of “anthraquinone derivatives Santiago–Teja, and Kumar–Johnston” [29,30]. AQ1–AQ7”.

Tsai et al. studied the dissolution of “1,5- diaminobromo-4,8-dihydroxyanthraquinone (CI Disperse Blue 56) and (CI Disperse Violet 1)” (Figure 9) in scCO_2 at different pressures and temperatures with varying times of contacts with or Figure 11. Structure of “(a) 1,4-diamino-2,3- without “ethanol or dimethyl sulfoxide (DMSO)” as dichloroanthraquinone (C.I. Disperse Violet 28) and (b) co-solvents. In co-solvents' presence, the 1,8-dihydroxy-4,5-dinitroanthraquinone”. equilibrium improved dramatically; however, much better results were obtained with DMSO [26,27]. MATERIALS INTERNATIONAL | https://materials.international| 376 Development of textile dyeing using the green supercritical fluid technology: A Review • • • Tamura et al. measured the solubility of “1- recorded a sequence of “ red 82 > blue 79 > amino-4- hydroxyanthraquinone (CI Disperse Red modified yellow 119” [33]. 15) and 1-hydroxy-4- nitroanthraquinone” under ScCO2 at different pressures and temperatures ranges utilizing a flow-type system. They reported that the solubility of “1-amino-4- hydroxyanthraquinone” exceeds that of “1- hydroxy-4- nitroanthraquinone”. The models of “Mendez-Santiago-Teja, Kumare- Johnston, Chrastil, and Sunge-Shim” were utilized in this study [31]. Also, Tamura et al. investigated the solubility of “anthraquinone derivatives, namely mono- substituted –NH2 and –NO2 of 1-nitro anthraquinone and 1-aminanthraquinone” (Figure 12,13) in ScCO2 at various ranges of pressure and temperature. The results showed that solubility is inversely proportional to temperature at pressures value lower than 19 MPa [32]. Figure 14. Chemical structure of “disperse azo dyes (a) disperse blue 79, (b) modified yellow 119,(c) disperse red 82”.

Figure 12. The structure of (a) 1-amino-4- Also, Fasihi et al. studied the solubility of “ 4- hydroxyanthraquinone , (b) 1-hydroxy-4- (N,N-dimethylamino)-4`-nitroazobenzene (D1), 4- nitroanthraquinone. (N,N-diethylamino)- 4`- nitroazobenzene (D2) and para red (D3)” (Figure 15) under ScCO2 at a various range of pressure and temperature. The results revealed the enhancement of solubility values upon the increase in supercritical carbon dioxide density. Besides, the melting point of the dyes affected the solubility resulting in the following sequence D2>D1>D3 in the decreasing order [34].

Figure 13. Reaction sequence for the synthesis of 1- butylamino- and 1,4-bis(butylamino)-2-alkyl-9,10- anthraquinone dyes –

4.1.2. The solubility of disperse azo dyes. Many researchers investigated the solubility of disperse azo dyes in ScCO2. For example, Lin et al. Figure 15. The solubility of “disperse azo dyes (D1) 4- investigated the solubility of “disperse blue 79, red (N,N-dimethylamino)-4`-nitroazobenzene, (D2) 4- 82, and modified yellow 119” (Figure 14) using (N,N-diethylamino)- 4`- nitroazobenzene and (D3) para ScCO2 at a specific temperature of 393.2 K at red”. different values of pressure and contact times. The solubility improved linearly by increasing system Baek et al. studied the solubility of “C. I. pressure from 15 to 30 MPa. The solubility order Disperse Orange 30 dye” (Figure 16) in scCO2,

MATERIALS INTERNATIONAL | https://materials.international | 377 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • • utilizing a batch system of solid-fluid equilibrium at dioxo-1H-benzo[de]isoquinolin-2(3H)-yl] acetate different pressure and temperature values. (Dye 2), and 6{(E)2-[4-(diethylamino)phenyl]-1- Adopting the model of “Kumar and Johnston’s,” diazenyl}-2-propyl-1H-benzoisoquinoline-1,3(2H)- they reported that solubility of the dye under dione (Dye 3)” (Figure 18), under scCO_2 medium investigation is directly proportional to the density at different range of pressure and temperature. They of CO2 and pressure at a specific temperature [35]. found that solubility is directly proportional to system pressure at a specific temperature in the following sequence Dye 3 >Dye 1>Dye 2 [37]. Jinhua et al. measured the solubility of “CI. Figure 16. Chemical structure of CI. Disperse Orange Disperse Red 73, CI. Disperse Blue 183” (Figure 19) 30. and their mixture under scCO_2 medium at a different range of pressure-temperature utilizing a Using a dynamic apparatus, Banchero et al. static recirculation method. They observed a investigated the solubility of “disperse blue 79, similarity between the binary and ternary systems disperse orange 3, and solvent brown 1” in a regarding the solubility of “disperse red 73 and mixture of ScCO2 and ethanol (Figure 17). Higher disperse blue183” at specific pressure and solubility values were recorded upon adding in temperature. The solubility is directly proportional ethanol, which reduces the system pressure by a to pressure; however, it is affected by dye polarity as value of 10MPa [36]. seen from the lower solubility in ScCO2 of “disperse blue 183” due to its higher polarity compared with “disperse red 73” [38].

Figure 19. Chemical structure of “(a) CI. Disperse Red 73, (b) CI. Disperse Blue 183”

Figure 17. Chemical Structures of “(Disperse Orange 4.2. The solubility of reactive disperse 3, Disperse Blue 79 and Solvent brown 1)”. dyes. Long, et al. studied the solubility of a reactive disperse dye, which was synthesized from “CI Disperse Red 17” with a derivative of “1,3,5- trichloro-2, 4,6-triazine” as the reactive moiety (Figure 20) under ScCO2 medium. They acquired a system in line with a spectrophotometer. The study was performed at a different range of pressure and temperature at a contact time of three hours. The solubility of the RD dye understudy is directly proportional to system pressure under various isotherms and inversely proportional to system Figure 18. Structure of disperse azo dyes( Dye 1, Dye temperature, particularly at values for the system 2, Dye 3). above 373.15 K [39].

Hojjati et al. investigated the solubility of “ethyl 2-[6-{(E)-2-[4-(diethylamino)-2- methylphenyl]-1-diazenyl}-1,3-dioxo-1H benzoisoquinolin-2(3H)-yl] acetate (Dye 1), ethyl 2- Figure 20. Chemical structure of “reactive disperse dye [6-{(E)-2-3-hydroxy-2-naphthyl-1-diazenyl}-1,3- CI Disperse Red 17”. MATERIALS INTERNATIONAL | https://materials.international| 378 Development of textile dyeing using the green supercritical fluid technology: A Review • • •

5. Application of supercritical carbon dioxide on synthetic fabrics. Synthetic fibers, mainly polyethylene terephthalate (PET), polyamide (PA), polyacrylonitrile (PAN), and polypropylene (PP), are the most widely used polymers in the textile industry. These fibers surpass the production of natural fibers with a market share of 54.4% [40]. , The conventional dyeing process of synthetic fiber Figure 22. Color graphics dyeing with one-bath under discharges much waste-water that is contaminated ScCO2. by various kinds of dispersing agents, surfactants, With a particular dyeing frame of loose fibers and new dye. ScCO2 fluid, more and more, has been under scCO_2, Zheng et al. executed dyeing PET proved as environmentally benign media for fibers with disperse red 153 (Figure 23). The synthetic dyeing fiber. The application of these experimental results showed that the dyeing techniques can result in reducing waste and cost for execution of fibers was excellent on the dyeing the entire dyeing process of synthetic textiles. frame. Also, dyeing temperature had a strong 5.1. Polyester fabrics in supercritical influence on the color yield. With the unique dyeing carbon dioxide. frame of loose fibers, there was no improvement in Many reports have been published describing the results of colorfastness to washing and light [43]. the dyeing of PET fabrics under supercritical carbon dioxide medium. In this context, we have collected the most recent methods giving an insight into their pros and cons. Figure 23. CI. Disperse Red 153. Using “disperse scarlet red S-BWFL dye (CI Disperse Red 74)”, Long, et al. designed a novel Using disperse fluorescent yellow 82. Xiaoqing plant in pilot-scale for fabric rope dyeing (PET et al. endeavored to dye PET fabrics under scCO_2. They managed to get a satisfactory k/s values at a fabrics) with ScCO2 fluid for cleaner production of textiles. The results showed that the shades with moderate system temperature and pressure in only different color strength at different dyeing 1-hour time [44]. temperatures were leveling and brightly colored, as shown in (Figure 21) [41].

Figure 21. The rope dyeing products of different.

Zheng et al. investigated graphics dyeing of PET fabrics in scCO_2, utilizing some disperse dyes mainly “disperse red 60, disperse red 91, disperse blue 60, and disperse blue 73”. They proved that the Figure 24. Hydrazonopropanenitrile dyes with mixing ratio has a significant effect on the color antibacterial activity. graphics dyeing at a specific system temperature and Using disperse red 153 and its crude dye pressure (Figure 22). Besides, increasing compound (Figure 23) Huan-Da Zheng et al. performed the proportions led to enhance color graphics dyeing dyeing of PET fabrics under scCO_2. They studied with disperse dyes [42]. MATERIALS INTERNATIONAL | https://materials.international | 379 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • • the different parameters of dyeing (temperature, colorfastness of dyed samples gave excellent results time, and pressure). The results indicated that the with values ranged at 4-5 and 5 [47]. dyeing effect of crude dye for PET was better than Penthalaa et al. used un-expensive chemicals to that of Disperse Red 153 in the same dyeing prepare a series of “azo and anthraquinone” dye condition. As well, they executed the mass transfer derivatives for dyeing Nylon 6 under ScCO2 model of Disperse Red 153 in ScCO2 [45]. medium. The produced dyed Nylon 6 samples The first trial for dyeing and finishing of PET exhibited a brilliant color shade as well as excellent fabrics under ScCO2 was reported by Abou Elmaaty fastness properties [52]. et al., who applied novel 5.3. Dyeing polypropylene fabrics under “hydrazonopropanenitrile” dyes with antibacterial supercritical carbon dioxide. functionality for dyeing PET fabrics under scCO2 They were using a series of “1,4- (Figure 24). They also succeeded in executing the bis(alkylamino) anthraquinone “dyestuffs Miyazaki dyeing process at moderate conditions of system et al. dyed unmodified polypropylene fibers under temperature and pressure as well as low dye scCO_2 medium(Figure 26). The results showed concentration. The fastness properties of the dyed that the dyeability of unmodified PP fiber improved PET were found to be excellent [46]. by increasing the length of the alkyl chain part in the The same research group of Abou Elmaaty dye [53]. synthesized new 2-oxoacetohydrazonoyl cyanide disperse dye (Figure 25). They dyed PET fabric with ScCO2 as a medium. Excellent results of color uptake and fastness properties have been obtained [47].

Figure 26. Chemical structures of “1,4-bis(alkylamino) anthraquinone” dyes.

Figure 25. 2-oxoacetohydrazonoyl cyanide disperses Another attempt for Miyazaki et al. for dyeing dye. PP fibers under scCO_2 was reported. They utilized 5.2. Dyeing of Polyamide fabrics under some commercial disperse dyes with different supercritical carbon dioxide. structures, mainly “four quinophthalone, two Dyeing polyamide fabrics under supercritical anthraquinones, three isothiazole-fused anthrone carbon dioxide medium is less abundant than PET, and four pyridone azo” derivatives. Unfortunately, and a few reports were found in literature. One the hydrophobic character of the dyestuffs under investigation, along with their aliphatic failed the strategy to dye Nylon 6 under ScCO2 is the utilization of disperse dyes. [48-50]. These reports dyeing process [54]. showed that both affinity and solubility are the most Under scCO_2 medium, Laio et al. studied the critical factors utility of “CI disperse red 60 and C.I disperse orange Abou Elmaaty et al. presented one-step dyeing 76 “ for dyeing PP fabrics (Figure 27). The results of Nylon 6 fabric utilizing the same series of gave a better affinity of PP fabrics under ScCO2 “hydrazonopropanenitrile” disperse dyes under than in water. However, the results of wash fastness were meager as the existing hydrophobic ScCO2 medium (Figure 24). The process produced potent antibacterial fabrics with excellent color interactions between dye and PP fibers [55]. strength and colorfastness under moderate conditions of temperature and pressure [51]. Also, Abou Elmaaty et al. synthesized a new “2-oxoacetohydrazonoyl cyanide” dye with excellent solubility in ScCO2. They applied these Figure 27. Chemical structures of C.I Disperse dyes for dyeing nylon six fabric under ScCO2 Orange 76. medium. They reported optimum dyeing pressure and temperature of 25 MPa and 403 K. The Under scCO_2 medium in the one-step dyeing process, Garay et al. studied the dyeing of PP with

MATERIALS INTERNATIONAL | https://materials.international| 380 Development of textile dyeing using the green supercritical fluid technology: A Review • • • commercial acid dye (Isolan 2S-RB®) using water as co-solvent (5% H2O). The good dyeing results were obtained for pressures above 17.5MPa [56]. Abou Elmaaty et al. utilized a series of “hydrozonopropanenitrile” dyes for dyeing unmodified PP fabrics under aqueous and supercritical Medium (Figure 28). They reported a moderate condition for dyeing PP in both aqueous and ScCO2 medium [57].

Scheme 1. Structure of disperse dyes.

Abou Elmaaty et al. investigated the first semi- pilot scale experiment to dye PP. They synthesized five new disperse dyes involving “Butyl 4-((2-(3- chlorophenyl)-1-cyano-2-oxoethyl) diazenyl) benzoate” for dyeing unmodified PP fabrics under both aqueous and ScCO2 mediums (scheme 1). The dyed fabrics exhibited excellent color strength and fastness properties. The adopted strategy unequivocally assured that an industrial scale dyeing of PP under ScCO2 is accessible. However, more

Figure 28. Structures of hydrozonopropanenitrile dyestuffs in different colors should be produced dyes. [58].

6. Application of supercritical carbon dioxide on natural fabrics

While ScCO2 is suitable for synthetic dyeing micelle were much dependent on the characteristics fabrics, natural fibers such as cotton, wool, and silk of the co-surfactant, that is, the chain length of the can only be dyed with extreme difficulty. To design alcohol. and develop a proper dyeing process to overcome these limitations, several different methods are reported in the literature to adapt the SFD process to the coloration of natural fibers [59,60]. 6.1. Dyeing protein fabrics under supercritical carbon dioxide. Using ScCO2 Guzel et al. performed dyeing of wool fibers with mordant dyes (Figure 29). They used three mordant dyes that have chelating ligand properties, 2-nitroso-1-naphthol (C.I. Mordant Brown), 5-(4- aminophenylazo) salicylic acid (C.I. Mordant Yellow 12) and 1,2- dihydroxyanthraquinone (C.I. Mordant Red 11) Figure 29. Chemical structures of (a)C.I. Mordant which were dissolved in scCO_2, and five different Brown(MD-1) , (b) C.I. Mordant Yellow 12(MD-2) and mordanting metal ions, Cr(III), Al(III), Fe(II), (c) C.I. Mordant Red 11(MD-3). Cu(II) and Sn (II) [61]. Sawada et al. investigated the solubilization of They found that 1-pentanol was the most water and ionic dyes in the ScCO2/pentaethylene suitable co-surfactant that assists the formation of glycol-octyl ether (C8E5) reverse micellar system. stable reverse micelles. Conventional ionic dyes The water solubility and stability of the reverse MATERIALS INTERNATIONAL | https://materials.international | 381 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • • were satisfactorily solubilized in the micelle's Zheng L. et al. reported that the pressure interior, even at low temperatures and pressures. release rates had significant damage to the scale Also, the reverse micellar system comprising layer of wool fibers. The color difference results pentaethylene glycolnoctyl ether (C8E5)/1- indicated that the pressure release rate became pentanol has been used for the solubilization of an faster; the brightness value became small. The faster acid dye and the subsequent dyeing of protein fibers the pressure release rate's speed, the greater the in ScCO2 [62]. destructive force to the scale layer. Therefore, in Sawada and Ueda investigated the order to avoid the deterioration of the damage solubilization of conventional ionic dyes in ScCO2 degree of the scale layer structure of wool fibers, the using (Perfluoro- 2,5,8,11-tetramethyl-3,6,9,12- pressure release rate can be controlled as slowly as tetraoxapentadecanoic acid ammonium salt) as a possible [67]. surfactant. They found that the pre-prepared The same research group reported wool surfactant was dissolved in ScCO2 without the textiles' dyeing with reactive Lanasol dyes (Figure presence of entrained. Further, a dissolved 32) in ScCO2. According to the results observed by surfactant can form micellar aggregates and SEM, it was shown that the solubility of dyes on the incorporate a small amount of water inside of the surface of wool fibers was increased by adding aggregates. They also found that conventional ionic entrainer. The results showed that the coloration dyes such as acid dyes, reactive dyes, and basic dyes increased with the amounts of entrainer in the were soluble in the microemulsion system in ScCO2 scCO_2 and the textiles [68]. [63]. They also reported that a reverse micellar system consisted of perfluoro-2,5,8,11-tetramethyl- 3,6,9,12-tetraoxapentadecanoic acid ammonium salt/ CO2/water (Figure 30) had a high possibility of solubilizing conventional acid dyes and dyeing wool fabrics in this system. Also, the density of CO2 Figure 32. Reaction of reactive dyes with a textile in this system cannot significantly affect the amino group. dyeability of the acid dye on wool [64]. Schmidt et al. investigated dyeing protein fibers in ScCO2 without pre-treatment of the fiber. The results indicated that high color yields and excellent fastness dyeing were obtained with 2- bromoacrylic acid. Furthermore, for the 2-

Figure 30. Structure of Perfluoro- 2,5,8,11- bromoacrylic acid-modified dye, it was found that tetramethyl-3,6,9,12- tetraoxapentadecanoic acid protein fibers can be dyed in higher color yields than ammonium salt. cotton because amino- and thiol-groups are Also, they dyed silk and wool fabrics in deep generally easier to activate than hydroxyl groups shades with conventional acid dyes from a reverse- [66]. micellar system (Figure 31) without special pre- Using ScCO2 Kraan et al. executed dyeing treatment using ammonium carboxylate with disperse dyes containing a reactive vinyl perfluoropolyether as a surfactant in scCO_2. It was sulphone or a dichlorotriazine group (Figure 33), found that on these fibers, the performance of acid various textiles containing PET, nylon, silk, wool or dyes was highly influenced by temperature and blends. The results showed that high coloration was carbon dioxide density. Conventional reactive dyes obtained when both the ScCO2 and the textiles were in this system were adsorbed on cotton, even in the saturated with water. At the saturation point, deep absence of dyeing auxiliaries. However, the fixation colors were achieved with the vinyl sulphone dye of the dye was not satisfactory [65]. for PET, nylon, silk , and wool, with fixation percentages between 70 and 92% when the dyeing time was two h. The positive effect of water was due to its ability to swell fibers or an effect of water on the reactivity of the dye–fiber system. Also, the dichlorotriazine dye showed more coloration when Figure 31. Reverse-micellar system. the ScCO2 was moist [69].

MATERIALS INTERNATIONAL | https://materials.international| 382 Development of textile dyeing using the green supercritical fluid technology: A Review • • • leveling property, and colorfastness, were achieved on wool in ScCO2 media [72].

Figure 35. Structure of synthesized SCF-X-ANR02 dye.

6.2. Dyeing cotton fabrics under supercritical carbon dioxide. Cotton is one of the most utilized fabrics in the industry of textiles. The production of cotton

Figure 33. Disperse dyes containing a reactive vinyl around the globe is approximately twenty-five tons sulphone or a dichlorotriazine group (on various textiles per year and a world consumption share of 34% in containing PET, nylon, silk, wool, or blends. recent years. It is the consumer’s essential products owing to its outstanding performance Xujun Luo et al. Developed a new synthetic characteristics. The main properties of cotton are route to synthesize azo-based disperse dyes excellent absorbency of water, and moisture, air containing the vinyl sulphonyl (Figure 34). This dye permeability, and high retention of heat, was used to color wool fibers using ScCO2 as the smoothness, and relaxing upon wearing. dyeing medium. The optimum dyeing process was However, a more significant challenge in carried out with water pre-treatment. Under optimal ScCO2 processing is the dyeing of cotton fabrics. conditions, which are relatively moderate for Hydrophobic fibers can be dyed under ScCO2 supercritical dyeing processes, the dyed wool fabrics medium with high color strength using commercial produced uniform dyeings with high color strength disperse dyes, however hydrophilic fibers or natural and fastness properties [70]. fibers (cotton, viscose) are difficult to dye using this medium with high fastness properties and high color depth. The problem of dyeing natural fibers under ScCO2 arises from the lack of capacity of CO2 to sufficiently break massive intermolecular hydrogen bonding that exists throughout the fibers Figure 34. Structure of 4-[2-[4- (mainly cotton). High hydrogen bonding in natural (ethenylsulphonyl)phenyl]diazenyl]-N,N- fibers hinders dyes' diffusion into the polymer diethylbenzenamine (RD 1). chains, resulting in unacceptable, low fastness properties [73]. Yue Fan et al. synthesized a novel Many approaches have been developed to anthraquinonoid disperse reactive dye for the control the restrictions of scCO_2 dyeing of natural coloration of natural fibers involving a versatile fibers. Several different methods are reported to bridge group to improve the coloration properties enlarge the dyeing capacity of cotton and other of the dye in ScCO2. The result shows that a good, natural fibers. They can be outlined in three main commercially acceptable colorfastness under methods: hydrophobic chemical modification of the standard washing conditions was achieved [71]. cotton, Physical modification to ease the solvation Yue Fan et al. designed a special dye of SCF- and transportation of the dyestuff to the fabric, and X-ANR02 for dyeing wool in a green ScCO2 media utilization of the dye molecules [74]. containing an anthraquinonoid chromophoric The first one is the hydrophobic chemical system and a dichlorotriazine reactive group, as modification of cotton; it enlarges its affinity for the shown in (Figure 35). The preliminary application hydrophobic dyestuff and ScCO2. These pre- results revealed that excellent dyeing properties of treatments have the drawback that they change both the synthesized SCF-X-ANR02 dye, such as the structure and characteristics of the fabric by a coloration behaviors and color characteristics, chemical reaction.

MATERIALS INTERNATIONAL | https://materials.international | 383 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • • The chemical modification of cotton fibers The second strategy is a physical modification improves the substantivity of hydrophobic using auxiliary agents to ease the solvation and disperses dyes by increasing the hydrophobic transportation of the dyestuff into the cotton fabric. character of these fibers upon reactions which bind Many reports have used bulking agents to disrupt bulky aryl residues to the fibers through a covalent the hydrogen bonds in the cotton fibers, therefore bond. For example, “Özcan et al.” studied the increase swelling under ScCO2, enhancing the utilization of disperse dyes in dyeing modified penetration of the dye into the cotton. Several cotton fabrics under ScCO2. The modification problems arise using these auxiliary agents. process was carried out using benzoyl chloride Beltrame et al. carried out the dyeing of cotton (Figure 36). The results presented a satisfactory fibers with natural and disperse dyes under ScCO2 color strength and colorfastness to washing. Also, medium. The k/s was significantly improved upon they performed the reaction at a lower system treating cotton with “polyethylene glycol (PEG)”, a temperature than that used for PET dyeing [75]. known plasticizer of cellulose. Simultaneously, fairly good washing and light fastness were obtained if PEG-treated cotton was dyed under ScCO2 with

Figure 36. Cotton fabric was modified with benzoyl disperse dyes in benzamide crystals [60]. chloride. The dye fixation has been a problem even though the dyeability of the modified cotton with Özcan et al. investigated the modification of polyethylene glycol was increased. Besides, this type cotton fabrics with benzoyl chloride and sodium of pre-treatment has led to a noticeable change in benzoyl thioglycollate (Figure 37) then dyeing the the cotton properties. Those changes include modified fabrics under scCO2 medium with handling weakness, increasing utilization of energy, “APAN [1-(4-aminophenylazo)-Z-naphthol] and and limiting the expansion of this technology to DY82 (C.I Disperse Yellow 82) at 373 K, 30 MPa” industrial scale. [76]. Maeda et al. investigated the dyeing of pre- modified cotton fabrics with “tetraethylene glycol dimethyl ether (TEGDME) or N-methyl-2- pyrrolidinone (NMP)” with reactive disperse dyes under supercritical medium (Figure 39). They increased the solubility of the dye into ScCO2 by adding a co-solvent, mainly acetone. The co-solvent Figure 37. Modification of cotton fabrics with improved penetration of the dye to the fabric and “benzoyl chloride and sodium benzoyl thio glycollate”. caused a higher color strength. This work also reported a higher colorfastness when using reactive Using ScCO2, Schmidt et al. reported on the disperse dye [78]. dyeing of cotton modified fabric with the reactive fiber group “2,4,6-trichloro-1,3,5-triazine” (Figure 38). The modification was performed in a mixture of acetone and water replacement of organic solvents. Higher dye uptake is obtained as a result of modification “CI Disperse Yellow 23” under ScCO2; however, the washing fastness was reduced. At the same time, no change was observed for crocking and lightfastness for dyed modified cotton in water or acetone [77].

Figure 39. Dyeing of pre-modified under ScCO2 medium. Figure 38. Modification of cotton with the reactive fiber group” 2,4,6- trichloro-1,3,5-triazine.” MATERIALS INTERNATIONAL | https://materials.international| 384 Development of textile dyeing using the green supercritical fluid technology: A Review • • • Utilizing water/CO2 microemulsions “reverse Moreover, it will be challenging to recycle carbon micellar systems” Sawada et al. endeavored to deal dioxide in the presence of such solvents. with the restrictions of natural fabrics dyeing under In the reverse micellar process, there is a lack supercritical medium (Figure 40). They used of dyes that can dissolve easily to the system as well “anionic surfactant reverse-micellar” system in an as the burdensome of removing surfactants on the organic medium. As a consequence, the solubility of fibers. Overall, the results of color strength and the reactive dye under investigation increased and colorfastness were inferior to those obtained from penetrated the cotton fabric efficiently. Under traditional aqueous dyeing [81]. suitable conditions, the dyeing of cotton in a Recently, a new strategy is adopted to improve reverse-micellar system is equivalent to that in a the dyeability via the design of dyes soluble in the conventional aqueous system. The color uptake was hydrophobic ScCO2. Mimicking the mechanism satisfactory; however, they pre-modified the cotton used for fixation of the cotton to reactive dyes in with a cationization agent to further improve the aqueous dyeing led to a group of dyes knowing as dyeing properties. This modification also lowered reactive disperse. A disperse dye is hooked to a the system temperature and pressure required for reactive group capable of anchoring to the reaching the optimum conditions compared to functional groups in the natural fabrics through a previous reports [80,81]. covalent bond. The following is a screening of the endeavors made by researchers in this context. Schmidt et al. utilized “CI. Disperse Yellow 23” dye hooked to “ 1,3,5-trichloro-2,4,6-triazine and 2-bromoacrylic acid groups”. This RD dye was used to dye unmodified natural fibers under ScCO2 (Figure 42). The results indicated that a higher color strength and colorfastness were obtained with “2- Figure 40. Dyeing in reverse- micellar system. bromoacrylic acid over “1,3-dichloro-2,4,6- triazine” as fiber [66]. Through physical interactions with the cotton, Cid et al. established a different procedure to process cotton under supercritical medium, excluding the pre-treatment step. They firstly impregnated the cotton fabric in an organic solvent and, at the same time, increasing the amount of co- solvent. This processing increased dye uptake and Figure 42. Structures of the RD dyes. colorfastness of the RD dye under investigation (Figure 41). They also reported on the use of the dye Gao et al. studied the dyeability of a new class as a solution in DMSO or methanol to improve dye of RD dyes based on “1,3, 5- trichloro-2,4,6- penetration into fabric [82]. triazine” moiety(Figure 43). This report proved that polarity of the dye structure plays a vital role in the solubility of the dye, non-polar groups cause a better dissolution in the hydrophobic ScCO2 medium [59].

Figure 41. Structure of nonpolar reactive disperses dye.

Despite the reasonably good results obtained from the reports mentioned above, cotton processing under supercritical medium on industrial or even pilot scale was not handy. This shortage was attributed to the high cost of the safety precautions required for processing under high pressure, especially in the presence of flammable solvents. Figure 43. Structure of RD dyes with a “1,3, 5 trichloro-2,4,6-triazine group”.

MATERIALS INTERNATIONAL | https://materials.international | 385 Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish • • • The same research group synthesized a new swelled the cotton fabric with water before dyeing class of RD dyes based on “halogenated acetamide under supercritical carbon dioxide. Cotton showed reactive group” (Figure 44). Un-modified cotton good color strength results [70]. fabric was dyed with the new dyes. Considering the Yue Fan et al. employed the “SCF-X-ANR02” absence of co-solvent, they assumed that the nitro dye for coloring cotton under ScCO2 containing “an group in the structure of the dye is accountable for anthraquinonoid” chromophore and a increasing the dyeability of the cotton. They also “dichlorotriazine” reactive group, as shown in reported that the “anthraquinone dyes” are better (Figure 35) [72]. than “azo dyes” regarding both color strength and Juan Zhang et al. examined the dyeing of un- extracted color strength [83]. modified cotton fabric with “Reactive Golden Yellow K-2RA” (Figure 46) under ScCO2 fluid at different humidity. This strategy depends on increasing the hydrophilicity of supercritical carbon dioxide by moistening with water resulting in a better dye penetration to the fabric and initiation of the hydrogen bond formation, consequently better dye uptake. The controlling factors include system pressure and temperature, as well as CO2 humidity [85].

Figure 44. Molecular structure of the reactive disperse dyes.

Da-fa Yang et al. synthesized new RD dyes Figure 46. Structure of Reactive Golden Yellow K- with “mono- and bi-acyl fluoride reactive groups” 2RA. for dyeing un-modified cotton fabrics under ScCO2 medium (Figure 45). The results indicated that the In a recent publication, Hirogaki et al. proved fastness properties for wash and crocking were that water-free dyeing of cotton under a improved. The covalent bond formation is the main supercritical environment is possible amid using the reason for such fastness improvement [84]. proper dye. So, they proposed a scheme for the synthesis of “thiazolo divinyle sulfone “ RD dyes (Figure 47). The dyeing was carried out at normal conditions at a reasonable rate. However, this study was not complete, and several important factors Figure 45. Structure of “acyl fluoride reactive disperse should have been performed to prove the dye.” consistency of the method [86].

Xujun Luo et al. developed a new approach for the synthesis of “azo-based disperse dyes” Figure 47. Chemical structure of synthesized thiazole containing the “vinyl sulphonyl moiety”, as shown azo reactive disperses dye. in (Figure 34). However, in this method, they

7. Conclusions This review highlighted the importance of mainly PET and even Nylon, found the way to supercritical carbon dioxide in textile dyeing. It industrial applications. On the contrary, more screened the recent publications that work is necessarily required to approve the endeavored to make the technology accessible methodology for natural fabrics. for all kinds of fabrics, whether synthetic or natural. It seems that synthetic dyeing fabrics,

MATERIALS INTERNATIONAL | https://materials.international| 386 Development of textile dyeing using the green supercritical fluid technology: A Review • • •

Funding This research received no external funding. Acknowledgments This research has no acknowledgment. Conflicts of Interest The authors declare no conflict of interest.

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