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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
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-
friendly solvent known for its potentiality as a
replacement for aqueous textile wet processing,
mainly dyeing [1-4]. A supercritical fluid is a matter
in a closed system above its critical temperature and
pressure. It is difficult to determine the borderline
between the liquid and gaseous state. This state of
matter is known as a supercritical state. Although
several substances are useful as supercritical fluids,
carbon dioxide has been the most extensively
utilized [5].
In the textile industry, traditional textile wet
processing utilizes a vast volume of freshwater. This
copious water is given away as effluent
contaminated with unreacted dyes and auxiliary
chemicals. A remarkable share of the money is
spent eliminating this waste-water before the
disposal in the water streamlet [6,7]. Textile wet
processing can outstandingly get an advantage from
the utilization of scCO2 as a dyeing medium. scCO2
has lower mass transfer resistance and higher
diffusion rates than water. This property makes the
dye penetrates much faster into the fibers, leading
to slower reaction times. Besides, water-free dyeing
does not require drying and consequently saving
energy. Moreover, the absence of water prevents
dye hydrolysis, which is a significant problem in
traditional dyeing.
In scCO2, the wanted color shade is achieved
with a small concentration of the dyestuff. Also, the
unreacted dyestuff, as well as CO2, are recycled,
leading to cost-effective and green methodology [8].
Volume 2, Issue 3, Pages 0373-0390
2020
Review
ISSN: 2668-5728
https://materials.international
https://doi.org/10.33263/Materials23.373390
Received: 9.06.2020
Accepted: 2.09.2020
Published: 10.09.2020
https://materials.international/https://doi.org/10.33263/Materials23.373390https://orcid.org/0000-0002-4877-0085https://orcid.org/0000-0003-2658-9944https://orcid.org/0000-0002-9355-4285https://orcid.org/0000-0003-3387-5228https://orcid.org/0000-0002-2835-8392https://materials.international/https://doi.org/10.33263/Materials23.373390
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2. What is Supercritical Fluid?
The supercritical state is known as the fourth
state of matter. A supercritical liquid is characterized
as “a substance over its critical temperature and
pressure”. At these conditions, the liquid has
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
a much-increased “solvent capacity”. This conduct
happens since an increment in density diminishes
mean “intermolecular distance,” expanding the
number of interactions between the solvent and
solute [2,9].
Figure 1. Pressure-temperature diagram.
3. Supercritical carbon dioxide dyeing apparatus
A photograph of three types of supercritical
carbon dioxide machines is shown in Figure 2.
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
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].
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
equilibrium between dyes and the supercritical
solvent. Dye solubility data is one of the most
crucial factors for selecting the dyestuff and setting
up the system temperature and pressure optimally.
Since the beginning of the supercritical technology,
the solubility of substances in supercritical fluids
(c)
(a)
(b)
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(SCF) has been determined in detail, and several
articles reported on solubility [11,12].
The correlation results between the calculated
and experimental solubility were estimated with
three density-based models: (a) “Chrastil, Bartle; (b)
Mendez-Santiago–Teja models” (c) “Ziger–Eckert”
semi-empirical correlation.[13-15]. Also, using two
“cubic equation-of-state (EOS) models, namely the
“Peng–Robinson EOS (PR-EOS) and the Soave–
Redlich–Kwong EOS (SRK-EOS)”. [16,17]. This
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.
They also screened the different correlation
methods experimented in the reports for data
modeling. They arranged the compounds into
classes based on their chemical behavior “inorganic,
organometallic, aromatic, nonaromatic organic,
polymer”. Most of the applications favored
“ScCO2” as a medium [18].
4.1. The solubility of disperse dyes.
4.1.1. Solubility of anthraquinone disperse dyes.
Many studies reported on the solubility of
anthraquinone disperse dyes in “scCO_2” and
estimated the solubility using dynamic and static
processes.
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
employing a “flow method”. They also investigated
the effect of many C-atoms in alkyl-chain and
solubility of dyestuff, showing a maximum for
phenyl-derivative [19].
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-
methyl-9,10-anthraquinone (Q1), 1-amino-2-ethyl-
9,10-anthraquinone (Q2), 1-amino-2,3-dimethyl-
9,10-anthraquinone (Q3), and 1-amino-2,4-
dimethyl-9,10-anthraquinone (Q4)”. They
estimated the solubility of dyes under investigation
in a large scope of temperature and pressure. They
reported on the phenomena that, at constant system
temperature, the increase of pressure causes a
significant increase in solubility of dyes “Q1-Q4”.
On the other hand, increasing system temperature
resulted in a decrease in CO2 density. The order of
solubility of the dyes understudy is “Q3 > Q1 > Q2
>> Q4” respectively [20].
Figure 4. Structures of aminoanthraquinone
derivatives.
Bae et al. studied the effect of adding a solvent
to the dye on the solubility in scCO2. The results
indicated that the solubility of non-volatile solid in
the ternary system, inclusive of co-solvent, is
correlated very well with the liquid model. They
agreed that solubility of non-volatile solutes such as
“CI disperses red 60” (Figure 5), “phenanthrene,
fluorene and acridine” in SCF at different pressure,
temperature, and co-solvent concentration can be
determined by the liquid model without critical
characteristics and solute vapor pressure [21].
Figure 5. Disperse red 60.
Shamsipur et al. estimated the solubility of “
9,10-anthraquinone derivatives “(Figure 6), in
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 6. Structures of 9,10-anthraquinone derivative.
Bao et al. measured the solubility of “C. I.
disperse red 60” (Figure 5) in scCO_2 at various
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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
ScCO2 to study the relationship between dye uptake
on the fiber and dye solubility. The result proved
that polyester fiber's dye uptake increased up to 20
MPa but dropped after this value [23].
Gordillo et al. investigated the solubility of
“disperse Blue 14” (Figure 7) using ScCO2 at
different pressures and temperatures. They
correlated the solubility values by utilizing an
accurate thermodynamically model correlated to
state equations. Using correlated methods of
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
medium at different ranges of pressures and
temperatures. An acceptable solubility correlation
under the ScCO2 medium was recorded [25].
Figure 8. Structure of “anthraquinone derivatives
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
without “ethanol or dimethyl sulfoxide (DMSO)” as
co-solvents. In co-solvents' presence, the
equilibrium improved dramatically; however, much
better results were obtained with DMSO [26,27].
Figure 9. Chemical structure of “ (a) CI. Disperse
Violet 1, (b) C.I. Disperse Blue 5”.
Coelho et al. adduced the solubility of some
disperse dyes mainly, “(quinizarin) 1,4-
dihydroxyanthraquinone, (disperse red 9) 1-
methylaminoanthraquinone, and (disperse blue 14)
1,4-bismethylaminoanthraquinone” (Figure 10) in
ScCO2 at different pressures and temperatures. An
acceptable solubility correlation under ScCO2
medium was recorded [28].
Figure 10. Chemical structure of “(a) quininzarin, (b)
disperse red 9, and (c) disperse blue 14 dyes.”
Also, Alwi et al. investigated the solubility of
“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-
Santiago–Teja, and Kumar–Johnston” [29,30].
Figure 11. Structure of “(a) 1,4-diamino-2,3-
dichloroanthraquinone (C.I. Disperse Violet 28) and (b)
1,8-dihydroxy-4,5-dinitroanthraquinone”.
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Tamura et al. measured the solubility of “1-
amino-4- hydroxyanthraquinone (CI Disperse Red
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 12. The structure of (a) 1-amino-4-
hydroxyanthraquinone , (b) 1-hydroxy-4-
nitroanthraquinone.
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.
investigated the solubility of “disperse blue 79, red
82, and modified yellow 119” (Figure 14) using
ScCO2 at a specific temperature of 393.2 K at
different values of pressure and contact times. The
solubility improved linearly by increasing system
pressure from 15 to 30 MPa. The solubility order
recorded a sequence of “ red 82 > blue 79 >
modified yellow 119” [33].
Figure 14. Chemical structure of “disperse azo dyes (a)
disperse blue 79, (b) modified yellow 119,(c) disperse
red 82”.
Also, Fasihi et al. studied the solubility of “ 4-
(N,N-dimethylamino)-4`-nitroazobenzene (D1), 4-
(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 15. The solubility of “disperse azo dyes (D1) 4-
(N,N-dimethylamino)-4`-nitroazobenzene, (D2) 4-
(N,N-diethylamino)- 4`- nitroazobenzene and (D3) para
red”.
Baek et al. studied the solubility of “C. I.
Disperse Orange 30 dye” (Figure 16) in scCO2,
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utilizing a batch system of solid-fluid equilibrium at
different pressure and temperature values.
Adopting the model of “Kumar and Johnston’s,”
they reported that solubility of the dye under
investigation is directly proportional to the density
of CO2 and pressure at a specific temperature [35].
Figure 16. Chemical structure of CI. Disperse Orange
30.
Using a dynamic apparatus, Banchero et al.
investigated the solubility of “disperse blue 79,
disperse orange 3, and solvent brown 1” in a
mixture of ScCO2 and ethanol (Figure 17). Higher
solubility values were recorded upon adding in
ethanol, which reduces the system pressure by a
value of 10MPa [36].
Figure 17. Chemical Structures of “(Disperse Orange
3, Disperse Blue 79 and Solvent brown 1)”.
Figure 18. Structure of disperse azo dyes( Dye 1, Dye
2, Dye 3).
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-
[6-{(E)-2-3-hydroxy-2-naphthyl-1-diazenyl}-1,3-
dioxo-1H-benzo[de]isoquinolin-2(3H)-yl] acetate
(Dye 2), and 6{(E)2-[4-(diethylamino)phenyl]-1-
diazenyl}-2-propyl-1H-benzoisoquinoline-1,3(2H)-
dione (Dye 3)” (Figure 18), under scCO_2 medium
at different range of pressure and temperature. They
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.
Disperse Red 73, CI. Disperse Blue 183” (Figure 19)
and their mixture under scCO_2 medium at a
different range of pressure-temperature utilizing a
static recirculation method. They observed a
similarity between the binary and ternary systems
regarding the solubility of “disperse red 73 and
disperse blue183” at specific pressure and
temperature. The solubility is directly proportional
to pressure; however, it is affected by dye polarity as
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”
4.2. The solubility of reactive disperse
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
temperature, particularly at values for the system
above 373.15 K [39].
Figure 20. Chemical structure of “reactive disperse dye
CI Disperse Red 17”.
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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
discharges much waste-water that is contaminated
by various kinds of dispersing agents, surfactants,
and new dye. ScCO2 fluid, more and more, has been
proved as environmentally benign media for
synthetic dyeing fiber. The application of these
techniques can result in reducing waste and cost for
the entire dyeing process of synthetic textiles.
5.1. Polyester fabrics in supercritical
carbon dioxide.
Many reports have been published describing
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.
Using “disperse scarlet red S-BWFL dye (CI
Disperse Red 74)”, Long, et al. designed a novel
plant in pilot-scale for fabric rope dyeing (PET
fabrics) with ScCO2 fluid for cleaner production of
textiles. The results showed that the shades with
different color strength at different dyeing
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
mixing ratio has a significant effect on the color
graphics dyeing at a specific system temperature and
pressure (Figure 22). Besides, increasing compound
proportions led to enhance color graphics dyeing
with disperse dyes [42].
Figure 22. Color graphics dyeing with one-bath under
ScCO2.
With a particular dyeing frame of loose fibers
under scCO_2, Zheng et al. executed dyeing PET
fibers with disperse red 153 (Figure 23). The
experimental results showed that the dyeing
execution of fibers was excellent on the dyeing
frame. Also, dyeing temperature had a strong
influence on the color yield. With the unique dyeing
frame of loose fibers, there was no improvement in
the results of colorfastness to washing and light [43].
Figure 23. CI. Disperse Red 153.
Using disperse fluorescent yellow 82. Xiaoqing
et al. endeavored to dye PET fabrics under scCO_2.
They managed to get a satisfactory k/s values at a
moderate system temperature and pressure in only
1-hour time [44].
Figure 24. Hydrazonopropanenitrile dyes with
antibacterial activity.
Using disperse red 153 and its crude dye
(Figure 23) Huan-Da Zheng et al. performed the
dyeing of PET fabrics under scCO_2. They studied
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the different parameters of dyeing (temperature,
time, and pressure). The results indicated that the
dyeing effect of crude dye for PET was better than
that of Disperse Red 153 in the same dyeing
condition. As well, they executed the mass transfer
model of Disperse Red 153 in ScCO2 [45].
The first trial for dyeing and finishing of PET
fabrics under ScCO2 was reported by Abou Elmaaty
et al., who applied novel
“hydrazonopropanenitrile” dyes with antibacterial
functionality for dyeing PET fabrics under scCO2
(Figure 24). They also succeeded in executing the
dyeing process at moderate conditions of system
temperature and pressure as well as low dye
concentration. The fastness properties of the dyed
PET were found to be excellent [46].
The same research group of Abou Elmaaty
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 25. 2-oxoacetohydrazonoyl cyanide disperses
dye.
5.2. Dyeing of Polyamide fabrics under
supercritical carbon dioxide.
Dyeing polyamide fabrics under supercritical
carbon dioxide medium is less abundant than PET,
and a few reports were found in literature. One
strategy to dye Nylon 6 under ScCO2 is the
utilization of disperse dyes. [48-50]. These reports
showed that both affinity and solubility are the most
critical factors
Abou Elmaaty et al. presented one-step dyeing
of Nylon 6 fabric utilizing the same series of
“hydrazonopropanenitrile” disperse dyes under
ScCO2 medium (Figure 24). The process produced
potent antibacterial fabrics with excellent color
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
dyes for dyeing nylon six fabric under ScCO2
medium. They reported optimum dyeing pressure
and temperature of 25 MPa and 403 K. The
colorfastness of dyed samples gave excellent results
with values ranged at 4-5 and 5 [47].
Penthalaa et al. used un-expensive chemicals to
prepare a series of “azo and anthraquinone” dye
derivatives for dyeing Nylon 6 under ScCO2
medium. The produced dyed Nylon 6 samples
exhibited a brilliant color shade as well as excellent
fastness properties [52].
5.3. Dyeing polypropylene fabrics under
supercritical carbon dioxide.
They were using a series of “1,4-
bis(alkylamino) anthraquinone “dyestuffs Miyazaki
et al. dyed unmodified polypropylene fibers under
scCO_2 medium(Figure 26). The results showed
that the dyeability of unmodified PP fiber improved
by increasing the length of the alkyl chain part in the
dye [53].
Figure 26. Chemical structures of “1,4-bis(alkylamino)
anthraquinone” dyes.
Another attempt for Miyazaki et al. for dyeing
PP fibers under scCO_2 was reported. They utilized
some commercial disperse dyes with different
structures, mainly “four quinophthalone, two
anthraquinones, three isothiazole-fused anthrone
and four pyridone azo” derivatives. Unfortunately,
the hydrophobic character of the dyestuffs under
investigation, along with their aliphatic failed the
dyeing process [54].
Under scCO_2 medium, Laio et al. studied the
utility of “CI disperse red 60 and C.I disperse orange
76 “ for dyeing PP fabrics (Figure 27). The results
gave a better affinity of PP fabrics under ScCO2
than in water. However, the results of wash fastness
were meager as the existing hydrophobic
interactions between dye and PP fibers [55].
Figure 27. Chemical structures of C.I Disperse
Orange 76.
Under scCO_2 medium in the one-step dyeing
process, Garay et al. studied the dyeing of PP with
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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].
Figure 28. Structures of hydrozonopropanenitrile
dyes.
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
dyestuffs in different colors should be produced
[58].
6. Application of supercritical carbon dioxide on natural fabrics
While ScCO2 is suitable for synthetic dyeing
fabrics, natural fibers such as cotton, wool, and silk
can only be dyed with extreme difficulty. To design
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)
which were dissolved in scCO_2, and five different
mordanting metal ions, Cr(III), Al(III), Fe(II),
Cu(II) and Sn (II) [61].
Sawada et al. investigated the solubilization of
water and ionic dyes in the ScCO2/pentaethylene
glycol-octyl ether (C8E5) reverse micellar system.
The water solubility and stability of the reverse
micelle were much dependent on the characteristics
of the co-surfactant, that is, the chain length of the
alcohol.
Figure 29. Chemical structures of (a)C.I. Mordant
Brown(MD-1) , (b) C.I. Mordant Yellow 12(MD-2) and
(c) C.I. Mordant Red 11(MD-3).
They found that 1-pentanol was the most
suitable co-surfactant that assists the formation of
stable reverse micelles. Conventional ionic dyes
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were satisfactorily solubilized in the micelle's
interior, even at low temperatures and pressures.
Also, the reverse micellar system comprising
pentaethylene glycolnoctyl ether (C8E5)/1-
pentanol has been used for the solubilization of an
acid dye and the subsequent dyeing of protein fibers
in ScCO2 [62].
Sawada and Ueda investigated the
solubilization of conventional ionic dyes in ScCO2
using (Perfluoro- 2,5,8,11-tetramethyl-3,6,9,12-
tetraoxapentadecanoic acid ammonium salt) as a
surfactant. They found that the pre-prepared
surfactant was dissolved in ScCO2 without the
presence of entrained. Further, a dissolved
surfactant can form micellar aggregates and
incorporate a small amount of water inside of the
aggregates. They also found that conventional ionic
dyes such as acid dyes, reactive dyes, and basic dyes
were soluble in the microemulsion system in ScCO2
[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
in this system cannot significantly affect the
dyeability of the acid dye on wool [64].
Figure 30. Structure of Perfluoro- 2,5,8,11-
tetramethyl-3,6,9,12- tetraoxapentadecanoic acid
ammonium salt.
Also, they dyed silk and wool fabrics in deep
shades with conventional acid dyes from a reverse-
micellar system (Figure 31) without special pre-
treatment using ammonium carboxylate
perfluoropolyether as a surfactant in scCO_2. It was
found that on these fibers, the performance of acid
dyes was highly influenced by temperature and
carbon dioxide density. Conventional reactive dyes
in this system were adsorbed on cotton, even in the
absence of dyeing auxiliaries. However, the fixation
of the dye was not satisfactory [65].
Figure 31. Reverse-micellar system.
Zheng L. et al. reported that the pressure
release rates had significant damage to the scale
layer of wool fibers. The color difference results
indicated that the pressure release rate became
faster; the brightness value became small. The faster
the pressure release rate's speed, the greater the
destructive force to the scale layer. Therefore, in
order to avoid the deterioration of the damage
degree of the scale layer structure of wool fibers, the
pressure release rate can be controlled as slowly as
possible [67].
The same research group reported wool
textiles' dyeing with reactive Lanasol dyes (Figure
32) in ScCO2. According to the results observed by
SEM, it was shown that the solubility of dyes on the
surface of wool fibers was increased by adding
entrainer. The results showed that the coloration
increased with the amounts of entrainer in the
scCO_2 and the textiles [68].
Figure 32. Reaction of reactive dyes with a textile
amino group.
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-
bromoacrylic acid-modified dye, it was found that
protein fibers can be dyed in higher color yields than
cotton because amino- and thiol-groups are
generally easier to activate than hydroxyl groups
[66].
Using ScCO2 Kraan et al. executed dyeing
with disperse dyes containing a reactive vinyl
sulphone or a dichlorotriazine group (Figure 33),
various textiles containing PET, nylon, silk, wool or
blends. The results showed that high coloration was
obtained when both the ScCO2 and the textiles were
saturated with water. At the saturation point, deep
colors were achieved with the vinyl sulphone dye
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
the ScCO2 was moist [69].
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Figure 33. Disperse dyes containing a reactive vinyl
sulphone or a dichlorotriazine group (on various textiles
containing PET, nylon, silk, wool, or blends.
Xujun Luo et al. Developed a new synthetic
route to synthesize azo-based disperse dyes
containing the vinyl sulphonyl (Figure 34). This dye
was used to color wool fibers using ScCO2 as the
dyeing medium. The optimum dyeing process was
carried out with water pre-treatment. Under optimal
conditions, which are relatively moderate for
supercritical dyeing processes, the dyed wool fabrics
produced uniform dyeings with high color strength
and fastness properties [70].
Figure 34. Structure of 4-[2-[4-
(ethenylsulphonyl)phenyl]diazenyl]-N,N-
diethylbenzenamine (RD 1).
Yue Fan et al. synthesized a novel
anthraquinonoid disperse reactive dye for the
coloration of natural fibers involving a versatile
bridge group to improve the coloration properties
of the dye in ScCO2. The result shows that a good,
commercially acceptable colorfastness under
standard washing conditions was achieved [71].
Yue Fan et al. designed a special dye of SCF-
X-ANR02 for dyeing wool in a green ScCO2 media
containing an anthraquinonoid chromophoric
system and a dichlorotriazine reactive group, as
shown in (Figure 35). The preliminary application
results revealed that excellent dyeing properties of
the synthesized SCF-X-ANR02 dye, such as
coloration behaviors and color characteristics,
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
around the globe is approximately twenty-five tons
per year and a world consumption share of 34% in
recent years. It is the consumer’s essential products
owing to its outstanding performance
characteristics. The main properties of cotton are
excellent absorbency of water, and moisture, air
permeability, and high retention of heat,
smoothness, and relaxing upon wearing.
However, a more significant challenge in
ScCO2 processing is the dyeing of cotton fabrics.
Hydrophobic fibers can be dyed under ScCO2 medium with high color strength using commercial
disperse dyes, however hydrophilic fibers or natural
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
(mainly cotton). High hydrogen bonding in natural
fibers hinders dyes' diffusion into the polymer
chains, resulting in unacceptable, low fastness
properties [73].
Many approaches have been developed to
control the restrictions of scCO_2 dyeing of natural
fibers. Several different methods are reported to
enlarge the dyeing capacity of cotton and other
natural fibers. They can be outlined in three main
methods: hydrophobic chemical modification of the
cotton, Physical modification to ease the solvation
and transportation of the dyestuff to the fabric, and
utilization of the dye molecules [74].
The first one is the hydrophobic chemical
modification of cotton; it enlarges its affinity for the
hydrophobic dyestuff and ScCO2. These pre-
treatments have the drawback that they change both
the structure and characteristics of the fabric by a
chemical reaction.
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The chemical modification of cotton fibers
improves the substantivity of hydrophobic
disperses dyes by increasing the hydrophobic
character of these fibers upon reactions which bind
bulky aryl residues to the fibers through a covalent
bond. For example, “Özcan et al.” studied the
utilization of disperse dyes in dyeing modified
cotton fabrics under ScCO2. The modification
process was carried out using benzoyl chloride
(Figure 36). The results presented a satisfactory
color strength and colorfastness to washing. Also,
they performed the reaction at a lower system
temperature than that used for PET dyeing [75].
Figure 36. Cotton fabric was modified with benzoyl
chloride.
Özcan et al. investigated the modification of
cotton fabrics with benzoyl chloride and sodium
benzoyl thioglycollate (Figure 37) then dyeing the
modified fabrics under scCO2 medium with
“APAN [1-(4-aminophenylazo)-Z-naphthol] and
DY82 (C.I Disperse Yellow 82) at 373 K, 30 MPa”
[76].
Figure 37. Modification of cotton fabrics with
“benzoyl chloride and sodium benzoyl thio glycollate”.
Using ScCO2, Schmidt et al. reported on the
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 38. Modification of cotton with the reactive
fiber group” 2,4,6- trichloro-1,3,5-triazine.”
The second strategy is a physical modification
using auxiliary agents to ease the solvation and
transportation of the dyestuff into the cotton fabric.
Many reports have used bulking agents to disrupt
the hydrogen bonds in the cotton fibers, therefore
increase swelling under ScCO2, enhancing the
penetration of the dye into the cotton. Several
problems arise using these auxiliary agents.
Beltrame et al. carried out the dyeing of cotton
fibers with natural and disperse dyes under ScCO2
medium. The k/s was significantly improved upon
treating cotton with “polyethylene glycol (PEG)”, a
known plasticizer of cellulose. Simultaneously, fairly
good washing and light fastness were obtained if
PEG-treated cotton was dyed under ScCO2 with
disperse dyes in benzamide crystals [60].
The dye fixation has been a problem even
though the dyeability of the modified cotton with
polyethylene glycol was increased. Besides, this type
of pre-treatment has led to a noticeable change in
the cotton properties. Those changes include
handling weakness, increasing utilization of energy,
and limiting the expansion of this technology to
industrial scale.
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
improved penetration of the dye to the fabric and
caused a higher color strength. This work also
reported a higher colorfastness when using reactive
disperse dye [78].
Figure 39. Dyeing of pre-modified under ScCO2
medium.
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Utilizing water/CO2 microemulsions “reverse
micellar systems” Sawada et al. endeavored to deal
with the restrictions of natural fabrics dyeing under
supercritical medium (Figure 40). They used
“anionic surfactant reverse-micellar” system in an
organic medium. As a consequence, the solubility of
the reactive dye under investigation increased and
penetrated the cotton fabric efficiently. Under
suitable conditions, the dyeing of cotton in a
reverse-micellar system is equivalent to that in a
conventional aqueous system. The color uptake was
satisfactory; however, they pre-modified the cotton
with a cationization agent to further improve the
dyeing properties. This modification also lowered
the system temperature and pressure required for
reaching the optimum conditions compared to
previous reports [80,81].
Figure 40. Dyeing in reverse- micellar system.
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
colorfastness of the RD dye under investigation
(Figure 41). They also reported on the use of the dye
as a solution in DMSO or methanol to improve dye
penetration into fabric [82].
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.
Moreover, it will be challenging to recycle carbon
dioxide in the presence of such solvents.
In the reverse micellar process, there is a lack
of dyes that can dissolve easily to the system as well
as the burdensome of removing surfactants on the
fibers. Overall, the results of color strength and
colorfastness were inferior to those obtained from
traditional aqueous dyeing [81].
Recently, a new strategy is adopted to improve
the dyeability via the design of dyes soluble in the
hydrophobic ScCO2. Mimicking the mechanism
used for fixation of the cotton to reactive dyes in
aqueous dyeing led to a group of dyes knowing as
reactive disperse. A disperse dye is hooked to a
reactive group capable of anchoring to the
functional groups in the natural fabrics through a
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-
bromoacrylic acid over “1,3-dichloro-2,4,6-
triazine” as fiber [66].
Figure 42. Structures of the RD dyes.
Gao et al. studied the dyeability of a new class
of RD dyes based on “1,3, 5- trichloro-2,4,6-
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 43. Structure of RD dyes with a “1,3, 5
trichloro-2,4,6-triazine group”.
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The same research group synthesized a new
class of RD dyes based on “halogenated acetamide
reactive group” (Figure 44). Un-modified cotton
fabric was dyed with the new dyes. Considering the
absence of co-solvent, they assumed that the nitro
group in the structure of the dye is accountable for
increasing the dyeability of the cotton. They also
reported that the “anthraquinone dyes” are better
than “azo dyes” regarding both color strength and
extracted color strength [83].
Figure 44. Molecular structure of the reactive disperse
dyes.
Da-fa Yang et al. synthesized new RD dyes
with “mono- and bi-acyl fluoride reactive groups”
for dyeing un-modified cotton fabrics under ScCO2
medium (Figure 45). The results indicated that the
fastness properties for wash and crocking were
improved. The covalent bond formation is the main
reason for such fastness improvement [84].
Figure 45. Structure of “acyl fluoride reactive disperse
dye.”
Xujun Luo et al. developed a new approach for
the synthesis of “azo-based disperse dyes”
containing the “vinyl sulphonyl moiety”, as shown
in (Figure 34). However, in this method, they
swelled the cotton fabric with water before dyeing
under supercritical carbon dioxide. Cotton showed
good color strength results [70].
Yue Fan et al. employed the “SCF-X-ANR02”
dye for coloring cotton under ScCO2 containing “an
anthraquinonoid” chromophore and a
“dichlorotriazine” reactive group, as shown in
(Figure 35) [72].
Juan Zhang et al. examined the dyeing of un-
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 46. Structure of Reactive Golden Yellow K-
2RA.
In a recent publication, Hirogaki et al. proved
that water-free dyeing of cotton under a
supercritical environment is possible amid using the
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
should have been performed to prove the
consistency of the method [86].
Figure 47. Chemical structure of synthesized thiazole
azo reactive disperses dye.
7. Conclusions
This review highlighted the importance of supercritical carbon dioxide in textile dyeing. It screened the recent publications that endeavored to make the technology accessible for all kinds of fabrics, whether synthetic or natural. It seems that synthetic dyeing fabrics,
mainly PET and even Nylon, found the way to industrial applications. On the contrary, more work is necessarily required to approve the methodology for natural fabrics.
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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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Development of textile dyeing using the green supercritical fluid technology: A Review
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Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish
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