Inorganic Chemistry Communications 115 (2020) 107891

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Inorganic Chemistry Communications

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A review on classifications, recent synthesis and applications of textile dyes T

a,⁎ b a
Said Benkhaya , Souad M' rabet , Ahmed El Harfi
a
Laboratory Agro-Resources, Organic Polymers and Process Engineering (LARPOGP)/Organic and Polymer Chemistry Team (ECOP). Faculty of Sciences, University Ibn
Tofail, Kénitra, Morocco
b
Laboratory of Geosciences and Environment, Team Development Geo Resource and Renovation Territories, Department of Geology. Faculty of Science, University Ibn
Tofail, Kenitra, Morocco

GRAPHICAL ABSTRACT

ARTICLE INFO ABSTRACT

Keywords: The classification of textile dyes has become essential due to the remarkable increase in the type and number of
Anthraquinone dyes. The structural classification of these dyes can be determined by the following functional groups:
Azo and dispersed dyes Anthraquinone, azo, phthalocyanine, sulfur, indigo, nitro, nitroso, etc. taking into account their chemical
Indigo structures. Another classification was based on the method of applying these dyes on an industrial scale. The
Direct and reactive dyes
dyes are grouped together as dispersed, direct, acid, reactive, basic, vat, etc. In this review, the dyes will be
Color index numbers (C.I.)
studied in three different groups depending on the chemical structures with an overview on the synthesis of some
Environment
new dyes, color index numbers (C.I.) and application methods. Finally, it would be also interesting to briefly
discuss the effects of the textiles dyes on environment.

1. Introduction to synthesize quinine, has produced a new generation of dye, [3–6].

The textile dyeing industry has been in existence for more than
4000 years. For all but the last 150 years, the dyes were obtained from
natural sources, [1]. The big change in dyes came following the dis-
covery of Mauveine by William Henry Perkin, in 1856, while trying to
find a route to synthesise Quinine, a drug used to cure Malaria, the
scourge of many tropical countries, [2]. So, Henry Perkin, in attempting
Color prediction has taken off in the 21st century by many major pro-
ducers of pigments and dyes. Dyes are synthetic organic compounds
that are hydro or oil-soluble whereas pigments are insoluble, they re-
main in particulate form, [7]. Different organic dyes are in use in textile
for coloring the different products, [8]. Their chemical structures are
diverse, including for example azo and nitro dyes, phthalocyanine and
diarylmethane dyes with very different chemical and physical

⁎
Corresponding author.
E-mail address: said.benkhaya@uit.ac.ma (S. Benkhaya).

https://doi.org/10.1016/j.inoche.2020.107891
Received 13 January 2020; Received in revised form 11 March 2020; Accepted 16 March 2020
Available online 19 March 2020
1387-7003/ © 2020 Elsevier B.V. All rights reserved.
S. Benkhaya, et al.
Fig. 1. Representative example for the color index classification.
properties, [9]. Dyes are complex unsaturated organic substances that
absorb light and give color to the visible region, [10].
Inaddition, a dye is a substance having the property of absorbing
part of the visible spectrum (chromophore). The color is given by the
fraction of light not absorbed by the dye but reflichie. The con-
jugated double bonds constitute a chemical structure favorable to the
absorption of light. Thus, colorants often contain aromatic amines,
[11].
Dyes are characterized by their capacity to absorb light radiation in
the visible spectrum (from 380 to 750 nm). The transformation of white
light into colored light by reflection on a body or by transmission or
diffusion results from the selective absorption of energy by certain
groups of atoms called chromophoric groups.
The more or less intense coloration of the different substances is
linked to their chemical constitution, [12]. In fact, a dye is a body
capable of absorbing certain luminous radiations and then reflecting
the complementary colors, [13].
Prior to the middle of the 19th century, dyes are made from natural
materials like beet root, [14–16]. Natural dyes can be derived from
plants, insects/animals, and minerals, [17]. They are generally less al-
lergenic and toxic than synthetic dyes and generate wastewater that can
be treated by biodegradation, [18].
Antoniotti and others reported that, quinoxaline and its derivatives
are an important class of nitrogen-containing heterocycles used in the
synthesis of textile dyes, [19]. These dyes are a group of organic
compounds composed of two or more fused aromatic, [7,8].
Around 7 × 107 tons of synthetic dyes are produced annually for
textile industry worldwide, of which nearly 10% of the dyestuff is
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Inorganic Chemistry Communications 115 (2020) 107891
discharged to environment as effluent after dying and processing, [20].
Dye production can be assumed to increase in-line with expected in-
creases in textile fibre production, [21].
Dyes are applied practically in all areas of our daily life for painting
and dyeing paper, skin and clothing, [22]. Up to 50% of the dyes used
are not fixed to the textile fibre, but persist as pollutants in the liquid
phase, [23].
In fact, the dyes, those are organic compounds with three essential
groups in their molecules: the chromophore, the auochrome and the
matrix, [24]. The active site of the dye is the chromophore, it can
summarize the spatial localization of atoms absorbing light energy.
Chromophore-containing molecules feature extensively in surgical
practice, with synthetic dyes gaining popularity over endogenous op-
tical adjuncts, [25].
The chromophore consists of groups of atoms, the most common of
which are nitro (─NO2), azo (─N═N─), nitroso (─N═O), thiocarbonyl
(─C═S), carbonyl (─C═O), as well as the alkenes (─C═C─). The ab-
sorption of electromagnetic waves by the chromophore is due to the
excitation of the electrons of a molecule, [24]. The molecule that
contains them becomes chromogenic, [13]. The chromogenic molecule
has dyeing possibilities only by the addition of other groups of atoms
called “auxochrome” [13]. These auxochromic groups allow the fixa-
tion of the dyes and can modify the color of the dye. They may be acidic
(COOH, SO3 and OH) or basic (NH2, NHR and NR2). The rest of the
atoms of the molecule correspond to the matrix, the third part of the
dye, [24]. Textile dyes contain functional groups, such as carboxylic,
amine and azo groups, which cannot be easily treated with conven-
tional methods, [26].
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Table 1
Classification of textile dyes according to the chromophore, [27,48,52–56].
Class Chromophore Dye example

Azo

Cyanine

Xanthene

Nitro

Quinione-imine

Indigoid

Acridine

Oxazine

Anthraquinone

Triarylmethane

Phthalein

Triphenylmethane dyes, [57]

(continued on next page)

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Table 1 (continued)

Class Chromophore Dye example

Nitroso

Nitro

Diarylmethane

Fig. 2. Different classes of dyes and their Color Index (C.I.) constitution numbers.

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Disperse Red 9

Disperse Violet 26

Disperse red 60

Disperse Brown 1

C.I. disperse blue 56

C.I.disperse red 60

C.I. disperse blue 79

C.I.disperse yellow 114

Disperse Red 19 (DR19)

Disperse Red 58

Fig. 3. Chemical structure of of some disperse dyes.

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C.I. Disperse Red 278

C.I. Disperse Red 8

Disperse Red 17

C.I. Disperse Red 7

Disperse Blue 124

C.I. Disperse Orange 3

Disperse Blue 106

Disperse Blue 1

C.I. Diserse blue 79

Disperse blue 14 dye

Fig. 3. (continued)

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Fig. 5. Different structure of compound (A).

Fig. 4. Synthetic of dispersed azo dyes (C).

In general, the dyes consist of an assembly of chromophoric,

auochromic groups and conjugated aromatic structures (benzene
rings, anthracene, perylene, etc.). When the number of aromatic
nuclei increases, the conjugation of the double bonds increases. The
energy of the p-bonds decreases while the activity of the electrons π
or n increases and produces a displacement towards the long lengths
wave. Similarly, when an electron-donor auxochromic group (amino,
hydroxy, alkoxy, etc.) is placed on a conjugated aromatic system, this
group joins the conjugation of the p-system, there may be hy-
perconjugation and the molecule absorbs in large wavelengths and
gives darker colors, [27].
There are about 8000 chemically different synthetic dyes, listed in
the Color Index (C.I.), [22,23] under 40,000 trade names. Each colorant
is classified under a code name indicating its class, its color and an
order number.
The Reactive Black 5 is a diazo dye, was given as a representative
example to show the classification by color index, Fig. 1.
Fig. 6. Different structure of compound (B).
Textile effluents containing dyes are often very complex and require
intensive treatment. Nowadays, the combination of two or more oper-
ating techniques, using scientific progress allowing good control of the
process, has become an interesting alternative.
In addition, photocatalysis technology is particularly attractive to
researchers in the field of industrial effluent treatment. They are pro-
mising for wastewater treatment. In particular, it is well suited for the
elimination of aromatic compounds which present a potential danger to
the environment such as dyes, [30]. In this context, several studies have
been carried out in this area.

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Fig. 7. Different structure of compound (C).

Zinatloo-Ajabshir et Salavati-Niasari [31], were, studies the photo-
catalytic behavior of synthesized ZrO2 was examined by the degrada-
tion of eriochrome black T dye as a model of water contaminant.
Zinatloo-Ajabshir et Salavati-Niasari [32], Zinatloo-Ajabshir and
Salavati-Niasari have been prepared a new favorable material of na-
nocrystalline praseodymium oxide. it is used as a photo-catalyst for the
degradation of 2-naphthol under UV light. In addition, Abbasi et al.,
[33] have been studied the photocatalytic performance of the nano-
composite Fe2O3-TiO2 in the degradation of methylene blue under ir-
radiation with UV light.
Motahari et al., [34], have been preparing a basic nanoparticles of
NiO. This material has a highly efficient photocatalytic activity, with

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Direct Red 28

Direct Black 38

C.I. Direct Red 2

C.I. Direct Blue 86

C.I. Direct Blue 71

Direct Orange 26

Direct Blue 6

Fig. 8. Chemical structures of some direct dyes.

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Table 2
Examples of the certain direct dyes based an azo chromophore and C.I.no, [84].
Chemical structure C.I. no

Direct Yellow 22 (a) and Direct Yellow (b).

Direct Red 28 (c), Direct Yellow 12 (d), Direct Red 75 (e), Direct Orange 18 (f), Direct Red 250 (g),
Direct Orange 26 (h) and Direct Red 23 (i).

Direct Black 166 (j), Direct green 33 (k), Direct Black 150 (l), Direct Blue 78 (m).

(continued on next page)

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Table 2 (continued)

Chemical structure C.I. no

Direct Black 151(n), Direct Black 22 (o), Direct Orange 39 (p), Direct Black 19 (q) and Brown direct
dye. C.I. 35850 (r).

Triphenodioxazine direct dyes

Fig. 9. Reaction between the reactive dye

and the textile fibers.

promising applications in the treatment of industrial dyes wastewater,

Fig. 10. Structure of homo bifunctional reactive dye.
study of dyestuffs (rhodamine B).
Rostami-Vartooni et al., [35], have been studied the photocatalytic
degradation of methyl orange (MO) and Congo red (CR) by an Ag/TiO2
nanocomposite as photocatalyst in the presence of two high pressure
8 W mercury lamps irradiated with ambient temperature.
Zinatloo-Ajabshir et al., [36], have been studied erythrosine dye
degradation under UV light by photocatalytics of the nanostructure as
synthesized Nd2Zr2O7-Nd2O3 and Nd2O3.
Ghiyasiyan-Arani et al., [37], have been confirmed that copper
vanadium oxidenanostructures are promising materials with excellent
per-formance in photocatalytic applications for degradation oforganic
pollution under UV irradiation.
Mortazavi-Derazkola et al., [38], have been manufactured a new

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Fig. 11. Chemical structure of the a few reactive dyes.

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Fig. 12. Reaction of the coupling (I) and (II).

Fig. 13. Synthesis route for the cationic reactive dyes (Q).

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Fig. 14. Different structure of cationic reactive dyes (Q).

catalyst can be used as photocatalyst with magnetic base effective in the

field of water treatment in particular the degradation of organic pollution.
Beshkar et al., [40], have been prepared a new nanostructured
material made of highly photocatalytic copper chromite. This material
has been used for the degradation of acid blue 92 under visible light.
Monsef et al., [40], have been applied an ultrasound-assisted
method for the synthesis of NdVO4 nano-photocatalysts and study of
the elimination of the dye in contaminating water.
Zinatloo-Ajabshir et al., [41], have been prepare highly photo-
catalytically active praseodymium zirconate nanostructures for the
degradation and elimination of organic pollutants.
Morassaei et al., [42], hase been evaluated the photocatalytic be-
havior of the NaCl-Nd2Sn2O7-SnO2 nanocomposites by photo-
degradation of the dye erythrosine as a water pollutant.
Zinatloo-Ajabshir [43], have been Zinatloo-Ajabshir et al., Were
evaluated the catalytic performance of the photocatalyst Nd2O3 for the
photodegradation of the methyl violet contaminant under ultraviolet
light.
Fig. 15. Reactive dyes complexed with copper. Ghanbari et al., [44], have been synthesized a nanostructure ma-
terial based on thallium iodide cadmium and evaluated their

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Fig. 16. Synthesis of R1, R2, R3 and R4.

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S. Benkhaya, et al.
Fig. 17. Synthesis of R5 and R6.
photocatalytic performance in the degradation of toxic dyes such as
orange methyl and blue methylene.
There are several dye classification systems, but the most popular
are based on their chemical structure, source, nuclear structure and
industrial applications, [45].
However, the objective of this review is to describe the different
chemical classification of textile dyes including the chemical structure,
the color index and the application in the dyeing of textile substrates.
Finally, I reported the undesirable effect of these dyes on the ecosystem.
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Inorganic Chemistry Communications 115 (2020) 107891
2. Classifications of textiles dyes
Before the discovery of synthetic dyes, a limited number of natural
dyes. Therefore, the classification of dyes has become mandatory due to
the increase in the annual global production of dyes. they are estimated
at several tens of millions of tonnes, [46].
2.1. Chromophore structure and color index (C.I.)
Textile dyes could be classified according to their chromophore
S. Benkhaya, et al.
Fig. 18. Synthesis of R7.
structure, color and method of application in the color index,
[29,47,48]. Depending on the chromophores, dyes can beclassified in
various classes such as, triphenylmethane, azo, diphenylmethane, ox-
azine, xanthene, etc.), [49].
Textile dyes have a unique chemical structure for each color,
[50,51]. They are can be named according to the chemical structure of
their chromophoric group. The so-called chromogenic chromophore is a
group of atoms present in the dye structures responsible for its color.
Table 1 shows the classification of textile dyes according to their
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Inorganic Chemistry Communications 115 (2020) 107891
structure of the chromophore.
The group of atoms binds to the chromophore called auxochrome,
which enhances the color of the chromogen, [31,32]. The most
common chromophoric are (–C = C-),(-C = N-), (-C = O-), (-N = N-),
(–NO2) and quinoid rings, [19]. The available auxochromes are
(–CO2H), (–NH3), (-SO3H), and (–OH), [50,51,58].
Each colorant is assigned a color index (C.I.), composed of a generic
name and a chemical constitution number, Fig. 2, [46].
S. Benkhaya, et al.
Fig. 19. The synthesis of R8.
2.2. Industrial application categories
2.2.1. Disperse dyes
The majority of disperse dyes are based on azo structures; however,
violetand blue colours are often obtained from anthraquinone deriva-
tives, [59]. These dyes are frequently insoluble or sparingly soluble in
water, non-ionic in character and applied to hydrophobic fiberes from
an aqueous dispersion, [60]. They are predominantly used on polyester
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Inorganic Chemistry Communications 115 (2020) 107891
but have found application to nylon, cellulose acetate and acrylic fi-
beres, although some of the wet-fastness properties of the dyes on these
substrates are poor, [57,87]. Disperse azo dyes are the largest category
among disperse dyes that accounts for more than 50% of the total
disperse dyes, [63]. These dyes are among the persistent class of dyes
due to recalcitrant nature and non-biodegradable behavior, [64].
Disperse dyes are classified by their sublimation temperature: Class
A, dyes have the lowest sublimation temperature whilst Class D dyes
S. Benkhaya, et al.
Fig. 20. The synthesis of R9.
have the highest sublimation temperature. The sublimation tempera-
ture is also relative to the molecular size of the dyes. Class A dyes are
relatively small in molecular size whilst Class D dyes are significantly
larger than Class A dyes. These dyes were traditionally applied to
polyester at the boil with the inclusion of a carrier in the dye bath to
facilitate diffusion of the dye into the substrate, [65].
Disperse dye particles with nano sized can keep better stability espe-
cially in high temperature dyeing process, [66]. These dyes showed the
marked advantages over other types in their levelling properties, [67].
According to Glover, [68] has been reported, the dispersed dyes are
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Inorganic Chemistry Communications 115 (2020) 107891
essentially adsorbed onto the poly-amide fiber by attraction at polar
sites in a limited number and the dissolution mechanism is in fact al-
most marginal. Although this type of adsorption corresponds to well-
bonded fibers stronger than in the case of polyester where the dye is
dissolved, these bonds are easily broken by a polar link interrupter such
as water. The fastness to washing fibers of poly-amide dyes with dis-
perse dye are therefore mediocre. Thus, it is necessary to know the
solubility of the dye in the dyeing bath, its affinity for the various fibers
and the nature of the fixing. The latter is of variable force depending on
whether the dye-substrate bond is of the ionic, hydrogen, Van der Waals
S. Benkhaya, et al.
Fig. 21. Chemical structures of some vat dyes.
or covalent type, [69]. A typical disperse dye structures and C.I. no are
illustrated in Fig. 3.
Li et al. [70], six dispersed azo dyes have been synthesized. The
synthetic procedures are described in the Fig. 4.
Figs. 5, 6 and 7 shows different possible dye structures according to
R1-R4 substitutions.
2.2.2. Direct dyes
The first direct dye was Congo red, discovered in 1884, [47,71].
According to the same othor, [72] has been confirmed, the direct or
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Inorganic Chemistry Communications 115 (2020) 107891
Vat Blue 1 (synthetic indigo)
Vat Black 25
Indigo carmine (IC)
C.I Vat green 1
Vat Yellow 1
Vat acid Blue 74
substantive dyes, which have a strong affinity for cellulose fibres,
[97,99].
They are mainly used for coloring paper products, these dyes have
an appearance of solidity during washing (Jalandoni et al.,), [75].
Aspland el al., [76] and others, [68,77–79] have been confirmed to,
the direct dyes are classified.
According to many parameters such as chromophore, fastness
properties or application characteristics. The chromophoric group of
direct dyes includes azo, stibene, oxazine and phthalocyanine, with
some thiazole and copper complex azo dyes, [80]. Fig. 8 show some
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Table 3
Some basic dyes classes, [114].
C.I. no Chemical structure Class

Basic Blue 26 Triarylmethane

Basic Red 1 Xanthene

Fig. 22. Chemical structures of vat dyes anthraquinone, Bromo subtituent and Basic Green 1 Triarylmethane
Tyrian puple.

structures direct dyes, [73,74,81-83].

Anionic azo dyes constitute the major proportion of direct dyes.
Table 2 presents a classification based on the chemical structure of
certain direct dyes constituting an azo chromophore such as Monoazo,
Basic Yellow 2 Diphenylmethane
Disazo, Trisazo, Tetrakisazo and Triphenodioxazine.

2.2.3. Reactive dyes

Reactive dyes have become very popular due to their high wet
fastness, brilliance and range of hues, [85].
According to Mahmoodi et al., [86], reported that, reactive dyes are
widely used because of the ability of their reactive groups to bind to the
fibers, their stability and their processing conditions, etc. [87–91].

Fig. 23. Synthesis of Vat Orange 15.

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Basic Red 9 monohydrochloride

Basic Blue 11

Basic Brown 1(Bismarck Brown Y)

Basic Blue 3

Basic Blue 24

Basic Blue 6

Fig. 24. Chemical structure of the a few basic dyes.

These dyes are the second largest classes of dyes, [37,48]. These dyes • Trichloropyrimidine;
are capable of forming a covalent bond with the amine or sulfhydryl • aminochloro-s-triazine;
groups of proteins in textile fibers, [93,94], Fig. 9. • sulphatoethylsulphone;
Reactive dyes are used for dyeing cellulosic fibers, as well as a small • dichloroquinoxaline;
percentage of silk and wool fibers, [38,46,53,54]. Those dyes furnish a • aminofluoro-s-triazine;
wide gamut of shades of good light fastness,and excellent wash fastness • difluorochloropyrimide;
on cotton, better dyeing processing conditions and bright colours, • dichlorotriazin;
[50,60,61].
Khatri et al., [97] reported that, the most widely used reactive According to Hang Xiao et al., [98] and other, [66,67] have been
groups, in the order of increasing level of reactivity are: reported, the reactive dyes can be produced by the reaction of the

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C.I. Basic Blue 22

C.I. Basic Violet 2

Fig. 25. localized and delocalized charge basic dye.

Table 4
Example of the acid dyes.
C.I. Acid Red 249 dye

Acid Orange IV

Acid Blue 349

C.I. Acid Blue 7

(continued on next page)

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Table 4 (continued)

Acid Blue 83

C.I. Acid Blue 25 (AB25)

Acid Red 337

Acid Yellow 36

Acid Blue 147

C.I. Acid Blue 25 (anthraquinone)

Acid Violet 17

Acid Orange 7

Acid Black-234

24
S. Benkhaya, et al.
Fig. 26. Various chromophoric systems in sulphur dyes.
dichloro- s -triazine dye, [92] with an amine at temperatures in the
region of 25–40° C. This reaction resulting in the displacement of one of
the chlorine atoms. therefore producing e less reactive monochloro- s -
triazine dye. Fig. 10 shows a reactive dye composed of two vinylsulfone
reactive groups (homo bifunctional) and two anthraquinone and azo
chromophores, [100] (see Fig. 11).
These dyes are applied in the same manner to cellulose except that,
being less reactive than the dichloro- s -triazine dyes, they require a
higher temperature (80 °C) and pH (pH = 11) for fixation of the dye to
the cellulose to occur. Some reactive dyes are represented in the fol-
lowing figure [85,101].
The reactive dyes, Reactive Red-3, iscommercially available. During
the washing process, loss of reactive dyes are about 50% in their hy-
drolyzed and unfixed form. Thus, Reactive Red-3 contaminated in
wastewater must beworried, [102].
Xiao et al., [98] synthesized three cationic reactive dyes, according
to the reaction voices present in the Figs. 12 and 13.
Fig. 14 show different possible dye structures (Q) according to R
and X substitutions.
Some reactive dyes are bound with copper, chromium and nickel.
the decomposition of these dyes, they generate toxic heavy metals in
the recipient environment that can end up in the food chain, [87].
Fig. 15 illustrates reactive dyes complexed with copper, [103].
Nine aldehyde reactive dyes, designated R1-R9, were synthesized by
Xiao Chen et al., [99]. Figs. 16, 17, 18 and 19 show the synthetic route
of each dye.Fig. 20
2.2.4. Vat dyes
Aspland, Burkinshaw and Muzamil Khatri et al., [104–106], re-
ported that vat dye are known for better color fastness, character-
istically excellent light and wet fastness properties. They are mainly
soluble in hot water and some are soluble in the presence of little
Na2CO3. This dye class are intended for application to cellulosic fibers
because of their affinity for this last and their application on nanofibers
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Inorganic Chemistry Communications 115 (2020) 107891
Phenothiazonethianthrone
Thianthrene
Thiazone
Thiazole
has not been investigated to date, [107,108]. Indigo belongs to the
generic family of vat dyes. Its actual Colour Index numbers is C.I. Vat
Blue 1, [109].
The most important natural vat dye is Indigo or indigotin found as
its glucoside, indican, in various species of the indigo plant indigofera.
Fig. 21 shows the examples of the vat dyes, [107,108].
Preston has been reported, [96] derivatives of indigo, mostly halo-
genated (especially bromo substituents) provide other vat dye classes
including: indigoid and thioindigoid, anthraquinone (indanthrone, fla-
vanthrone, pyranthone, acylaminoanthraquinone, anthrimide, di-
benzathrone and carbazole), [96]. The typical chemical structure of vat
dye anthraquinone and bromo substituent are given in Fig. 22.
Thetford et al., [62] have been synthesized Vat Orange 15 Ac-
cording to the synthetic reaction route in Fig. 23.
2.2.5. Basic dyes
Hunger et al., [110] reported that, these dyes may have either the
positive charge located on an ammonium group or the delocalized
charge on the dye cation found in many triarylmethane, xanthenes and
acridine dyes, [111].
According to Silkstone, [112] and Other, [33,102] demonstrated
that , these dyes classes are applied with retarders because of poor
migration properties at the boil.
According to the same author, [112] reported that, the careful
control is necessary when using retarders so that anionic sites within
the substrate are not blocked which would restrict dye uptake making it
difficult to achieve dark shades. Some basic dyes with their chemical
structures and class are shown in Table 3.
According to Broadbent et al., [115] reported that, these dyes are
usually applied to acrylic, paper and nylon substrates, but can also find
use in some modified polyester substrates. The basic dyes contain a
quaternary amine group which most often forms an integral part of the
formula, but this is not systematic. Sometimes a positively charged
oxygen or sulfur atom replaces nitrogen.
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

N-[ p-(p-hydroxyanilino) phenyl ]

sulphanilic acid

Sulfur brilliant green, CI 53570

8-Anilino-5-(p-hydroxyanilino)-1–
naphthalenesulphonic acid.

Sulfur blue dye, CI 53235

1,8-Dinitronaphthalene.

Sulfur black, CI 53185

2',4'-Dinitroacetanilide

Leuco Sulfur black 1, C.I 53185

Phthalic anhydride

Fig. 27. Sulfur dyes very used.

Broadbent have been reported to, the basic dyes are water-soluble
and produce coloured cations in solution; these cations are attracted
electrostatically to substrates with a negative charge.
According to same author have been confermed to, the basic dyes
are water-soluble and produce coloured cations in solution; these ca-
tions are attracted electrostatically to substrates with a negative charge.
The chemical structure of few basic dyes are shown in Fig. 24.
Broadben et al., [115] has been reported, these dyes are usually
applied to acrylic, paper and nylon substrates, but can also find use in
some modified polyester substrates, [115]. Examples of a localized
(Basic Blue 22) and a delocalized (Basic Violet 2) charge basic dye are
given in Fig. 25.

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S. Benkhaya, et al.
Fig. 28. Possible tautomers of an azo dye.
2.2.6. Acid dye
Acoording to Hozet et al., [12] and other, [13] reported that, acid
dyes: As the name suggests, they are “acids”, the molecule has one or
more acid functions (SO3H and COOH), [12]. Their acid nature explains
their affinity for the basic functions of fibers, such as polyamides, [13].
As representative element of this family of dyes, mention may be made
of the red congo, [41,62].
These dyes, especially for sulfonic acid dyes, are widely used in the
textile, pharmaceutical, printing, leather, dye, paper and other fields
because of their brightcolors and high solubility, [117]
Lewiset al., [118] and other, [33,90,91] confermed that, the acid
dyes their usage constitutes about 30% 40% of the total consumption of
dyes, and they are applied extensively on nylon, cotton, wool, [116].
They are usually applied at acidic pH (Nunn et al.,), [119]. The example
of these dyes are shown in table 4, [120].
2.2.7. Sulfur dyes
The first sulphur dye has been prepared in 1873 by Croissant and
Bretonnière, [121]. In 1966, sulfur dyes represented 9.1% of total US
dye production and 15.8% of the dyes made for use on cellulosic fibers
[1], and the world production was estimated at 110,000–120,000 tons
per year, [122]. Sulfur dyes are a type of vat dye, [123].
Stolte et al., [124] and other, [113] demonstrated that, the sulfur
dyes they are high molecular weight dyes obtained by the sulfurization
of organic compounds. These commonly used dyes to dye cellulose,
They are converted into sodium-derived leuco by reduction using of
sodium sulfide, [124]. They are applied to the fiber from a substantive
leuco compound in the same way as for vat dyes, [123].
According to Jothi, [125] and other, [126] reported that, these dyes
are not chlorine resistant. In addition to that, the colorations obtained
have good light fastness and then water. They are mainly used for
dyeing cellulosic fibers (80% are black sulfur dyes).[69,73,74].
These dyes were ivised into four groups (Colour Index),
[22,31,79,84,86].
• sulfur dyes;
• Leuco sulfur dyes;
• solubilized sulfur dyes;
• condensed sulfur dyes.
Chromophoric systems based on phenothiazonethioanthrone,
thianthrene, thiazone and thiazole dye as their chromophore are pre-
sented in Fig. 26, [127].
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Inorganic Chemistry Communications 115 (2020) 107891
Aromatic compounds such as, benzene, naphthalene, diphenyl, di-
phenylamine, azobenzene, etc. nitro, nitroso, amino, substituted amino
or hydroxy are generally starting materials for the synthesis of sulfur
dye, [74,75]. Fig. 27 illustrates some sulfur dyes, [127].
2.2.8. Azo dyes
Azo dyes are the most used dyes. They are the main components of
the textile industry used in the dyeing process, [129]. They were re-
ported to constitute 60–70% of all dyestuff concerning textile produc-
tion, [130]. Azo dyes belong to the largest family of textile dye com-
prising of 60–70% of all textile dyes in practice, [131]. These dyes are
characterized by the functional group (-N = N-) uniting two symme-
trical and/or asymmetrical identical or non-azo alkyl or aryl radicals,
[132]. They constitute the largest family, including 70% of the world's
annual production of synthetic dyes, [133]. Azo colors are formed in-
side textiles, in situ, by the reaction of two colorless or slightly colored
compounds called naphthols, or C.I, [134]. Azo dyes containing het-
erocyclic rings lead to bright anddeepshade, [135]. Main disadvantage
of azo dyes is to give dull shades on blue-violet color range, [136].
Between 60 and 70% of azo dyes are toxic, carcinogenic. They are
resistant to biodegradability due to their chemical structure, [132,133].
From the 896 azo dyes with known chemical structure in the available
textile dyes database, 426 azo dyes (48%) can generate one or more of
the 22 regulated aromatic amines in the European Union in Annex XVII
of REACH, [137]. Between 7% and 8 % of azo dyes are prohibited by
government regulations as they can release carcinogenic aromatic
amines, such as benzidine and 3,3′-dimethylbenzidine, [138], as well as
Direct Black 38(DB38) is an azo dye classified as carcinogenic to hu-
mans due to its biotransformation to benzidine, [139]. Biodegradation
of azo dyes can generate amine byproducts that can be hazardous and
carcinogenic, [140].
In addition, azo dyes based on a heterocyclic system have become
an important part of the dye industry due to their color strength, ex-
cellent light fastness, brighter shades, etc., [141].
The biological treatment processes of these dyes tend to generate
recalcitrant aromatic amines, which are more toxic than the parent dye
molecule, [142].
Azo amino dyes are excellent examples of organic compounds
comprising a zwitterionic resonance system, Z. Fig. 28, shows a bone
example of possible tautomers of an azo dye, [143].
Synthetic azo dyes are currently used for food coloring more fre-
quently than natural ones and the field of their application is very wide
(non-linear optics, dye-sensitized solar cells, optical data storage,
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Fig. 29. Structure of some azo dyes.

Fig. 30. Aromatic hetero cyclic azo dye (A) as a function of substitutions R1, R2 and R3.

28
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Fig. 31. Different structure of aromatic heterocyclic azo dyes (A).

Fig. 32. Stage I.
metallochromic indicators and ink jet printers, etc.) [38,39]. Fig. 29
shows examples of monoazo, diazo and triazo dyes.
Voltammetric azo dyes determination offers many advantages, e.g.
high sensitivity, selectivity, speed, low investment and running cost,
and low laboriousness. Moreover, these methods are robust, re-
producible, user friendly, and compatible with the concept of green
analytical chemistry. This review is devoted to the critical comparison
of electrochemical sensors and measuring protocols used for voltam-
metric determination of most frequently used azo dyes in food.
Attention is focused on the working electrode and its possible mod-
ification which is crucial for successful determination,
[92,95,116,128,145,146].
Chang et al., [147] has been confirmed to, azo dyes are the most
widely used compounds in various fields, (textile, food, paper, printing,
leather and cosmetic industries, etc). [1,51].
According to Ganapati et al., [53] have been demonstrated to, the
azo dyes play a very crucial role in governing the market of dyeing and
printing. They are one of the most important categories of synthetic
dyes are easily synthesized from a simple method of diazotization and
coupling. Genal et al., synthesized six aromatic heterocyclic azo dyes
(A) are shown in Fig. 30, [144]. Fig. 31 show different possible dye
structures (A) according to R1, R2 and R3 substitutions.
Mallikarjuna et al., [148], have been synthesized of novel azo dyes
having sulfamethaxazole core: N-(5-methyl-1, 2-oxazol-3-yl)-4-[(E)-(3-
methyl-5-oxo-1-phenyl-4, 5-dihydro1H-pyrazol-4-yl) diazenyl] benze-
nesulfonamide of the empirical formula C20H18N6O4S noted A1; 4-[(E)-
(5-cyano-1-ethyl-2-hydroxy-4-methyl-6-oxo-1, 6-dihydropyridin-3-yl)
diazenyl]-N-(5-methyl-1, 2-oxazol-3-yl) benzenesulfonamide of the
empirical formula C19H18N6O5S noted A2 and 4-[(E)-(5-cyano-2-hy-
droxy-4-methyl-6-oxo-1, 6-dihydropyridin-3-yl) diazenyl]-N-(5-methyl-
1, 2-oxazol-3-yl) benzenesulfonamide of the empirical formula
C17H14N6O5S noted A3. The synthetic voice adopted for the preparation

29
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Fig. 33. Sage II.

Fig. 34. Reaction diazotization.

Fig. 35. Reaction coupling disperse azo dyes (I).

Fig. 36. Reaction coupling disperse azo dyes (II).

30
S. Benkhaya, et al.
Fig. 37. Different structure of disperse azo dyes (I).
of the dyes A1, A2 and A3 is divided into two stages (I and II) are
represented in Figs. 32 and 33, [148] (See Figs. 34, 35, 36).
Qui et al., [149] have been synthesis of novel disperse azo dyes with
aromatic hydroxyl group. The synthetic procedures are described ac-
cording to two stages diazotization and coupling the following figures
(34 and 35).
Fig. 37 show different possible disperse azo dye structures (I) ac-
cording to R1 and R2 substitutions.
Fig. 38 show different possible disperse azo dye structures (II) ac-
cording to R1 and R2 substitutions.
Table 5 illustrates a classification of textile dyes according to their
industrial application categories, characteristics and applications,
[22,28,30].
3. Impact of textile dyes on environment
World production of textile dyes is estimated at more than 10,000
tonnes per year and around 100 tonnes/year of dyes are released to
wastewater [164]. in addition, textiles are the second most polluting
industrial sector in the world today. Many fatal and irreversible
environmental consequences, such as the disappearance of the Aral
Sea, due to the overconsumption of water to irrigate cotton fields,
[165].
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Inorganic Chemistry Communications 115 (2020) 107891
Fig. 38. Different structure of disperse azo dyes (II).
Consequently, the textile industry is responsible for an undesirable
impact on the environment, [166]. During the dyeing process of textile
substrates, a remarkable quantity of synthetic dyes is released into the
environment due to a lack of affinity for the surfaces to be dyed, [167].
Textile industry effluents are very colorful due to the frequently
used alkaline dyes and are characterized by high salinity and ecotoxi-
city, [132,169], in particular with regard to water pollution and waste
gases emitted by water worn , [169]. The dyes can be partially de-
graded or transformed in the water and sediments of rivers receiving
treated wastewater, [170]. In addition, dyes and their breakdown
products are mutagenic, teratogenic and carcinogenic, [171]. In addi-
tion, around 40% of dyes worldwide contain organically bound
chlorine, [172]. Many dyes are difficult to discolor due to their complex
structure and synthetic origin, [173]. In fact, the treatment of raw
textile effluents is very difficult, due to its inherent heterogeneous,
weakly biodegradable and toxic compositions, [174,175].
4. Conclusion
In the light of this review, we can conclude that there are many
synthetic dyes in terms of different application methods (reactive dye,
acids dye, basic dye, vat dye, dispersed dye, direct dye, sulfur dye, etc.),
chromophore groups such as anthraquinone, azo, phthalocyanines,
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Table 5
Classification of textile dyes according to industrial application categories [110,113,150–152].
Categorie of dye Structure Characteristics and applications

Acid Waltres et al., [153] have been reported, the degree of colour fastness varies directly with dye molecule size. Acid
dyes are applied to textile substrates of the type: polyamide, wool, silk, paper, inks, leather, ink-jet printing,
cosmetics, etc.

Reactive The fixation of reactive dye requires temperature above 60 ° C, [154,155]. They are mainly required for dyeing
and printing of cotton fibers, [156].

Disperse Ding et al., [157], have been confirmed dispersed dyes are the only dyes suitable for dyeing poly (ethylene
terephthalate)

Direct The direct dyes are relatively inexpensive. They are available in a full range of hues but are not of high colour
brilliance, [41,42]. They are applied in ellulose fibres, cotton, viscose, paper, leather, polyamide.

Basic Chakraborty et al., [159], have been reported, the basic dyes are cheaper, soluble in alcohol and methylated spirit
but not easily soluble in water while a few are sparingly soluble. They are applied in synthetic fibers, paper, inks.

Vat The vat dyes are known for better color fastness and their application on nanofibers has not been investigated to
date, [104]. They have an affinity for cellulose, cotton, viscose, wool;

Sulfur Khatari et al., [160] have been confirmed, the sulphur dyes possess neither well defined chemical structures nor
consistent in composition; are just specified with raw material and process used to manufacture. Indeed, excess
sulphur is isolated from dye after synthesis. This dyes are inexpensive and are used mainly for dyeing textile
cellulosic materials or blends of cellulosic fibers; [161].

Metal complex dye Chakraborty et al., [158] have been reported, the metal complex dyes are mostly acid dyes possessing chelating
sites to enable these to be combined with metal atoms, . They are applied to textile substrates of the type wool, silk
and nylon to produce fast shades.

Azoic These dyes are applied to textile fibers such as cotton, rayon, cellulose acetate and polyester.
Azoic, sulfur, and disperse dyes are insoluble in water, [103].

(continued on next page)

32
S. Benkhaya, et al. Inorganic Chemistry Communications 115 (2020) 107891

Table 5 (continued)

Categorie of dye Structure Characteristics and applications

Mordant Millington et al., [162], have been reported many mordant dyes commonly used in the textile industry form
coordination complexes at the surface of nanocrystalline TiO2. They are characterized by a low affinity for certain
textile substrates. As well as, they demand a bite in their industrial applications, [45]. They are applied to textile
fibers such as wool, leather and silk.

Vacchi et al., [163] have been confirmed, the disperse azo dyes are poorly water-soluble compounds, they become
dispersed in water because their commercial formulations contain surfactants needed for the dyeing process. They
are applied to textile fibers such as polyester, polyamide, plastic.

triphenylmethanes, indigoids, xanthenes, polymethines and nitrosed,
etc. as well as color index numbers (C.I.).
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://
doi.org/10.1016/j.inoche.2020.107891.
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Dr. Said Benkhaya, I am 33 years, I was born in Kénitra
Morocco. I have a PhD in Fundamental and Applied
Chemistry in 2019. The title of my thesis subject was:
Performance of Ultrafiltration of New Synthetized
Membranes Homogens, Composites and Composites
Layered of Azo Chromophore Dyes AO74 and OM.
Molecular Dynamic Simulation. I Have 15 articles in-
dexed in national and international journals. In addi-
tion, 32 communications presented at national and in-
ternational conferences. My area of skill are : ✓ Dye
chemistry ; ✓ Writing reviews on classifications and
applications of textile dyes ; ✓ Synthesis and char-
acterization of organic and composite membranes.
Applications to ultrafiltration of dyes ; ✓ Synthesis and
characterization of novel thermoplastic organic and composite membranes for re-
moval of dyes textile.