development of textile dyeing using the green ......development of textile dyeing using the green...

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

Heba Sorour, Tarek Abou Elmaaty, Abdallah Mousa, Hatem Gaafar, Ali Hebeish

• • •

MATERIALS INTERNATIONAL | https://materials.international| 374

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)

https://materials.international/

Development of textile dyeing using the green supercritical fluid technology: A Review

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MATERIALS INTERNATIONAL | https://materials.international | 375

(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



• • •


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”.



• • •


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,



• • •


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”.



• • •


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



• • •


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


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



• • •


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


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



• • •


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].



• • •


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


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.



• • •


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.



• • •


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”.



• • •


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.



• • •


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 ......development of textile dyeing using the green...

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