Journal of Cleaner Production 167 (2017) 14e22

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Journal of Cleaner Production

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Review

Color and chemical constitution of natural dye henna (Lawsonia

inermis L) and its application in the coloration of textiles
M.A. Rahman Bhuiyan a, *, A. Islam a, A. Ali a, M.N. Islam b
a
Department of Textile Engineering, Dhaka University of Engineering and Technology, Gazipur, 1700, Bangladesh
b
Department of Chemistry, Dhaka University of Engineering and Technology, Gazipur, 1700, Bangladesh

a r t i c l e i n f o a b s t r a c t

Article history: The natural dye henna usually being recognized as lawsone is a red-orange pigment that has long been
Received 15 February 2017 used for the coloration of skin and hair as well as textile materials. This natural colorant garners the
Received in revised form attention of researchers throughout the globe for the coloration of textile materials due to the fact that its
14 August 2017
color can easily be harmonized with nature besides its slight chemical reactivity without posing any
Accepted 16 August 2017
Available online 17 August 2017
environmental problems. So, a large number of studies were carried out on both extraction and appli-
cation of henna dye in textile fibers along with the standardization and simplification of dyeing tech-
niques. This review article is mainly focused on the contemporary research works on henna dye
Keywords:
Natural dye
highlighting the general characteristics alongside its chemical composition and chromatic properties. A
Henna leaves greater emphasis is also placed on the dyeing chemistry of the natural dye henna as well as its appli-
Lawsone cations in the dyeing of cellulosic, protein and synthetic textile fibers including the effects of different
Cellulosic fiber mordants and mordanting methods on the dye uptake. Moreover, the scope of improvement in terms of
Protein fiber dyeability and overall colorfastness properties through chemical modification of textile fibers has also
been mentioned.
© 2017 Elsevier Ltd. All rights reserved.

Contents

1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14
2. General properties of henna . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15
3. Color and chemical constitution of lawsone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15
4. Application of henna dye in textile coloration . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16
4.1. Cellulosic fiber . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16
4.2. Protein fiber . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
4.3. Nylon fiber . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19
4.4. Polyester fiber . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20
5. Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21

1. Introduction textile materials (Saxena and Raja, 2014). These dyes have been
used for the dyeing of textile materials and have become a regular
The natural dyestuffs imply and refer to all the coloring mate- ritual of human lives from time immemorial (Alam et al., 2007).
rials derived or extracted from nature i.e. of the plant, animal, However, with the advent of synthetic dyes in the second half of the
mineral and microbial origins are used for coloration of a variety of nineteenth century alongside an extensive research in the field of
synthetic dyestuffs has led to a drastic decline in the use of natural
dyes in textiles because of their limited range of colors, lack of
* Corresponding author. reproducibility and uneven shades, poor color yield and poor to
E-mail address: arahman@duet.ac.bd (M.A.R. Bhuiyan). moderate colorfastness properties as well as the dearth of

http://dx.doi.org/10.1016/j.jclepro.2017.08.142
0959-6526/© 2017 Elsevier Ltd. All rights reserved.
 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22
information regarding methods of improving the fastness and color
value (Samanta et al., 2007).
On the other hand, synthetic dyes are attractive as textile col-
orants due to their availability, economical, brilliant shades and
excellent color fastness properties (Bhuiyan et al., 2013) but un-
fortunately some of these synthetic colorants are found to be
allergic, carcinogenic and deleterious to human health and envi-
ronment (Siva, 2007). This is why; there has been a revival of in-
terest in the application of non-allergic, non-toxic and eco-friendly
natural dyes in textile fibers because of their high compatibility
with the environment, as well as the availability of various viable
natural coloring resources (Bhuiyan et al., 2017a).
In recent years, a huge body of research (Geelani et al., 2016;
Shabbir et al., 2016; Punrattanasin et al., 2013; Ghoreishian et al.,
2013; Shahid et al., 2012; Yusuf et al., 2012; Rekaby et al., 2009)
has been made across the globe to explore the extraction of natural
dyes from various sources such as plant, animal and minerals as
well as an optimization of their application process through over-
coming the limitations for the coloration of textile fibers. Among
them henna dye belonging to the classification of plant origin and
chemically quinonoid in nature has also been thoroughly investi-
gated by researchers for its extraction and application in vegetable,
protein and synthetic fibers (Bhuiyan et al., 2017a; Yusuf et al.,
2015; Rehman et al., 2012; Dev et al., 2009). The natural dye
henna which grows most abundantly in Bangladesh, India,
Pakistan, Egypt, Yemen, Iran and Afghanistan (Kasiri and Safapour,
2014) is a shrub or small plant, and the powdered leaves of this
plant (aqueous paste) are generally being used as a sort of cosmetic
for staining skin, hands, hairs and beards (Yusuf et al., 2012).
Henna commonly being known as lawsone or hennotannic acid,
a red-orange pigment, is the chief constituent of henna leaves
(Rehman et al., 2012). Based on the illustration of industrial clas-
sifications, lawsone is Natural Orange 6 and CI 75480 which is
chemically known as 2-hydroxy-1, 4-naphthoquinone (Scheme 1)
and acts as a substantive dye for protein fiber as well as other textile
fibers and imparts an orange color on the substrate (Gulrajani et al.,
1992). Again, like other natural dyes, it has a number of remarkable
advantages, such as it does not pose any hazard to health, is easily
harmonized with nature having a slight chemical reactivity without
any adverse environmental problems.
Recent years have witnessed a surge in studies on the
O form (Fig. 1) after drying and separating the branches and twigs
8 2007). The conversion of dried leaves to powder is carried out by
8a
7 1
2 3. Color and chemical constitution of lawsone
6 4 3
4a
5 Kingdom
O Family
Scheme 1. Chemical structure of lawsone (2-hydroxy-1, 4-naphthoquinone).
15
standardization of the process for the extraction and application of
henna dyes in textile fibers. Increasing efforts are also being made
for the simplification and modification of the existing dyeing
techniques to improve its fastness properties, particularly washing
and color yield. The purpose of the present review is to mainly
concentrate on the current research on henna dyes emphasizing
their properties and dyeing chemistry as well as their extractions
and applications in the dyeing of cellulosic, protein and synthetic
textile fibers. The organization of this article is devoted to the
general properties of henna dye followed by the chemical compo-
sition and coloration of different textile fibers highlighting the
dyeing performance i.e. color strength and fastness properties of
the substrates dyed with henna.
2. General properties of henna
Henna, a flowering plant with gray-white appearance, has
spines and consists of different parts such as leaves, bark, roots,
fruits and flowers (Udeani, 2015). The plant is highly branched,
deciduous, glabrous, a small plant that attains a height of 1.8e7.6 m
(Bailey and Bailey, 1976). The scientific classification of henna refers
to the Lawsonia inermis, belonging to the family of Lyrthaceae
(Table 1) along with different names around the globe such as
Mehandi, Heena, Al-Khanna, Al-Mehandi, Mendee, Egyptial etc.
 which
The name henna has originated from the Arabic word ḥinna
has been used for the coloration of skin and hair from ancient times
and is available in the form of a paste, decoction and powder
(Bhuvaneswari et al., 2002).
The leaves of henna grow opposite to each other on the stem
usually in pairs having the length of 1.5e5.0 cm and 0.5e2.0 cm in
width (Makhija et al., 2011). They are sub-sessile, elliptical and
lanceolate (long and wider in the middle), acuminate (tapering to a
long point) with depressed veins on the dorsal surface (Sastri,
1962). The leaves of henna are greenish brown in color (Fig. 1)
with a characteristic odor as well as a bitter and astringent taste and
contain a red-orange pigment, lawsone which provides the well-
known coloring properties of henna. Again, the highest dye con-
centration resides in the petiole (the central vein) of the leaves and
the young leaves contain the highest petiole dye content compared
to the older leaves which contain a lower quantity of dye.
Lawsone is the active ingredient of henna leaves along with
gallic acid, white resin, sugars, tannin and xanthones (Bhadane
et al., 2015). Fresh henna leaves are generally used in the powder
from the dried henna leaves through manual and mechanical
methods to render the purest and most intense color (Alam et al.,
pulverization, and moisture is usually removed from henna powder
OH upon heating in the oven.
Lawsone is derived from the hennoside precursors in the henna
leaf, and the molecule of lawsone is 2-hydroxy-1, 4-
Table 1
Scientific classification of henna (Yadav et al., 2013).
Division
Class
Plantae
Magnoliophyta
Magnoliopsida
Order Myrtales
Genus
Lythraceae
Lawsonia
Species L. inermis
16 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22
(I)
Fig. 1. Henna leaves (I) and powder from henna leaves (II) after grinding.
naphthoquinone which resembles to the molecular structure of
naphthalene. Again, in the chemical structure of lawsone (Scheme
1), two oxygen atoms are attached to the naphthalenic carbons at
positions of 1 and 4 to form 1, 4-naphthoquinone, and a hydroxyl
group (eOH) of enolic nature is present at position 2 (Almeida et al.,
2012). In addition, the chemical formula of lawsone is C10H6O3 that
corresponds to the total molecular weight of 174.16 atomic mass
units (Parfitt, 1999).
Lawsone is partially soluble in water with a varying degree of
solubility depending upon the composition of the sample. It is a
weak acid and forms soluble salts in alkaline solution (Gurjar et al.,
2014). The ionization of lawsone in water (Scheme 2) is associated
with the unstable negatively charged structure due to the presence
of 2 carbonyl groups (> C]O) and an enolic (eOH) group while
both the ionized and unionized species are involved in a pH-
dependent equilibrium. The acidic solution of lawsone is color-
less, but with an increased pH values an absorption maximum
develops around 450 nm that gives rise to a characteristic orange
color of the material dyed with henna (Batran, 2015; Gupta and
Gulrajani, 1994). It is probably caused by the development of a
tautomeric form which predominates in an alkaline solution lead-
ing to a more intense color than the species associated with low pH
values. Again, the absorptions of UVeVis spectrum of lawsone in
dimethyl sulfoxide (DMSO) are observed at 296, 339, 416 and
448 nm wavelengths that commonly arise due to transitions from n
to p* or p to p* (Mahkam et al., 2014). Besides, the solution of
henna in acetonitrile is very pale yellow and gives an absorption
band at 333 nm, but it turns intense yellow upon dilution with
water (Hijji et al., 2012). Depending on the solvent and other con-
ditions, henna may experience two successive 1-electron re-
ductions or a 2-electronreduction which may or may not be
accompanied by the transfer of protons (Schemes 3 and 4).
In addition, the yellow solution is typically provided by 1, 4-
naphthoquinone in contrast to the orange of 1, 2-naphthoquinone
results from the restriction of resonance arising out of the
O O
O tained from proteins are suitable for dyeing with henna due to their
OH
H henna is widely studied for the dyeing of nylon and polyester which
O O
Scheme 2. Dissociation of lawsone in water (Hijji et al., 2012).
(II)
stability of 1, 4-quinone groups which signify the presence of an
unsaturated bond joining the two aromatic rings. This rigidity of
bond restricts any development of canonical forms in which there is
a single bond joining the rings compared to 1, 2-quinones which
have canonical forms connecting both ring junctions (Amro et al.,
1993). In an alkaline aqueous solution of lawsone, the equilibrium
(Scheme 5) shifts in favor of 1, 2-naphthoquinone due to repulsion
arises from the close proximity of two negative charges: one, the
partial negative charge on 1-carbonyl oxygen due to its electro-
negativity and the other negative charge on 2-carbon enolic oxygen
due to deprotonation by the alkali. This also accounts for the
distinctive reddish-orange hue of an alkaline lawsone solution.
The infrared (IR) spectrum of lawsone in carbon tetrachloride
indicates the presence of carbonyl-stretching region with a doublet
at 1662 and 1672 cm
1 (Amro et al., 1993). The carbonyl-stretching
band of 1, 4-naphthoquinone corresponds to 1672 cm
1 while the
smaller one at 1662 cm
1 may be due to an enolic form carbonyl
stretch arises from keto-enol tautomerism (Sanderson et al., 2006).
The C]C vibrational bands of the naphthalene ring are observed at
1578 and 1592 cm
1 and band at 3170 cm
1 indicates the stretching
OeH which overlays the CeH vibrations (Mahkam et al., 2014).
Again, typically, the band for 2-naphthol lies at 3610 cm
1 whereas
that for lawsone is lower and placed at 3411 cm
1 (Amro et al.,
1993). A shift of this order occurs when the hydroxyl group is
intramolecularly hydrogen bonded to form a non-conjugated ring
which signifies the part of an undissociated form of lawsone ac-
cording to Scheme 6. Such a complication would become stable in
the 1, 4-diketo-2-hydroxy tautomer which should have the typical
yellow hue of 1, 4- naphthoquinones.
4. Application of henna dye in textile coloration
The application of henna dye in the coloration of textiles is
conducted for both natural and man-made textile fibers. Among
the natural fibers, vegetable fibers are the most popular apparel
fiber obtained from the cell wall of plants and are cellulosic in
composition. These fibers can be dyed with a wide range of syn-
thetic dyestuffs as well as natural dyes along with henna. Again,
wool and silk, the very commonly used natural textile fibers ob-
substantivity towards lawsone. In addition, the application of
are the most important classes of synthetic textile fibers.
4.1. Cellulosic fiber
Cellulosic textile fibers have originated from the natural
 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22 17

O O O
OH
OH OH
e- e-

O O O

Scheme 3. Reduction involving 1-electron without proton transfer (Hijji et al., 2012).

O OH (Gandini, 2008), and the fibers from cellulose can be categorized as

natural like cotton, flax, hemp, jute, sisal, kenaf, abaca, coir as well
OH OH as man-made such as viscose, polynosic, lyocell and modal (Gohl
and Vilensky, 1983). Naturally, these fibers hold cellulose polymer
2e-, 2H+
which is hydrophilic by nature having a long stretched macro-
molecule with primary and secondary alcoholic hydroxyl (eOH)
groups (one primary at the sixth carbon atom and two secondary at
the second and third carbon atoms).
OH The presence of countless polar eOH groups in cellulose
O
macromolecule is responsible for the reactivity, moisture absorp-
Scheme 4. Reduction involving 2-electron accompanied by proton transfer (Gurjar tion and swelling property of fiber (Bhuiyan et al., 2017b) which
et al., 2014). also facilitates the diffusion of dye into fiber pores as well as en-
hances the dyeing performance of cellulosic textile materials.
Therefore, the coloration of cellulosic fiber can be conducted with
O O
synthetic dyestuffs like direct, vat, azoic, sulfur and reactive dyes
(Bhuiyan et al., 2016).
O O
However, numerous studies (Gulzar et al., 2015; Haddar et al.,
2014; Rehman et al., 2013; Bhatti et al., 2012; Ratnapandian et al.,
2012; Pan et al., 2003) were also carried out across the globe on
the dyeing of cellulosic fibers with a variety of natural colorants
such as acacia, gulzuba, onion shells, deodara, jackfruit, eucalyptus
bark and tea along with henna or lawsone. Several inherent limi-
O O
tations such as poor color retaining properties and a low sub-
Scheme 5. Equilibrium of 1, 4-naphthoquinone and 1, 2-naphthoquinone structure. stantivity of lawsone towards cellulose preclude its extensive
applications in cellulosic fibers (Bhuiyan et al., 2017a). This may be
attributed to the polar nature of both cellulose and lawsone (hy-
O H droxyl groups are usually active sites) besides the complexity of
their natural aspects (Omer et al., 2015). As a result, a host of
research have been conducted for the treatment of cellulosic fibers
with UV irradiation (Iqbal et al., 2008) and mordanting with various

O
chemicals such as potash alum, ammonium sulfate, hydrosulfate
and caustic soda, copper sulfate and ferrous sulfate (Udeani, 2015;
Iqbal et al., 2008; Ali et al., 2009) in order to enhance the absorption
of dye by fiber and also improve the color fastness properties. It has
been reported that irradiated fabrics when dyed with methanolic
extracts of irradiated henna powder exhibited a much better color
strength and fastness properties than that of non-irradiated fabric
dyed with the same extracts of non-irradiated henna powder. This
is most likely due to the hydrolytic degradation of lawsone colorant
upon the UV treatment that causes a significant sorption of
degraded products on cotton fabrics. In addition, methanolic ex-
tracts of henna dye together with a UV irradiation of fiber
demonstrated a superior color fastness property against washing,
rubbing and light (Iqbal et al., 2008).
O
Scheme 6. Intramolecularly hydrogen bonded undissociated lawsone (Amro et al.,
1993).

cellulose polymer consisting of several hundreds to thousands of b

(1e4) linked D-glucose units (Scheme 7) with numerous hydroxyl
groups (Islam et al., 2016). The polymer cellulose, the most abun-
dant, a renewable polymer resource, is available worldwide today Scheme 7. Chemical structure of a cellulose polymer.
18 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22
For mordanting of cellulosic fiber, pre-mordanting, post-mor-
danting and simultaneous mordanting processes are employed. But
among all of them, the pre-mordanting process is mostly studied. It
has been observed that mordanted cellulosic fibers have a greater
dye uptake than that of un-mordanted fibers (Iqbal et al., 2008).
Besides, cotton fibers after mordanting exhibited a higher rate of
dye uptake compared to other cellulosic fibers for a similar shade
under the same dyeing conditions (Udeani, 2015). Moreover, the
color characteristics of henna-dyed fabric samples also vary not
only between mordanted and without mordanted dyed fibers but
also between pre-mordanted and post-mordanted fibers (Table 2).
However, no significant improvement was reported regarding color
fastness properties of dyed cellulosic fibers as a result of
mordanting.
The cationization is an alternative treatment process for cellu-
losic fibers which has widely been used to enhance the dyeing and
fastness properties of henna-dyed fabric (Omer et al., 2015).
The application of cationic agent like 3-chloro-2-
hydroxypropyltrimethylammonium chloride (CHPTMAC) (Scheme
8) instead of metallic mordants can be a novel technique for both
improvement of natural dyeing process and reduction of pollution.
The characterization of the cationized cellulosic fiber reveals that
the crystalline portion remained unchanged while a large number
of eOH groups of cellulose were substituted by grafting of catio-
nizing agents (Khalil-Abad et al., 2009). This cationized cellulosic
fiber attracts the anionic henna dye in aqueous solution through
strong ionic interaction leading to an improvement of color
strength and fastness properties along with outstanding UV pro-
tection characteristics (Omer et al., 2015).
In addition, among others, the effects of different processing
parameters such as salt concentration, dyeing time and tempera-
ture, material to liquor ratio and dyebath pH on the dye exhaustion,
color strength and fastness properties of henna-dyed cellulosic fi-
ber were also studied by researchers. The color strength i.e., K/S
value of dyed fabric was found to increase with an increment of
dyeing temperature and a maximum value was obtained at 70  C
temperature (Ali et al., 2009). The higher dye absorption due to an
elevated dyeing temperature indicates the higher swelling of fibers
along with solubility of henna dye, resulting in the opening up the
fiber structure that allows an increased penetration and diffusion of
dye molecules. Furthermore, a higher temperature also eliminates
the aggregation tendency of dye molecules leading to the reduction
of dye particle size (Ibrahim et al., 2010).
The impact of different salt (e.g. Na2SO4 or NaCl) concentrations
on the neutralization of the negative surface potential of cellulosic
fiber in aqueous solution (Broadbent, 2001) was observed due to
minimization of repulsion between anionic lawsone and cellulosic
fiber. The experimental results demonstrated that the amount of
salt is directly related to the exhaustion of dye by fiber, and a higher
exhaustion was obtained with a higher salt concentration (Ali et al.,
2009). Again, the effect of Na2SO4 is more pronounced than that of
NaCl on the dye exhaustion by fiber. Besides, the dyeing time has a
linear relationship with the color strength of dyed fabric, and a
Table 2
Color co-ordinates of cotton dyed with henna extracts with and without mordanting
(Ali et al., 2009).
Dyeing Color co-ordinates
L* a* b* C*
Dyeing without mordanting 46.80 5.73 27.06 27.66
Dyeing with pre-mordanting with alum 43.52 8.95 29.46 30.78
Dyeing with post-mordanting with alum 49.92 8.22 29.29 30.42
Dyeing with pre-mordanting with iron 18.58 4.14 2.58 4.88
Dyeing with post-mordanting with iron 16.42 1.86
0.15 1.86
maximum K/S value was reported for 100 min dyeing time (Iqbal
et al., 2008). Moreover, the dye bath pH and material to liquor ra-
tio have also played a significant role in the relative color strength
value of dyed fabric. The maximum dye absorption by fiber was
observed in the neutral dyeing condition i.e. at pH 7 whereas the
material to liquor ratio of 1:30 turned out to be the most suitable
for the highest dye absorption (Ali et al., 2009).
4.2. Protein fiber
The protein fibers from protein polymers have originated from
natural animal sources such as keratin (hair or fur) that are secreted
by insects and formed through polycondensation of a-amino acids
to make repeating units of polyamide (John and Thomas, 2012). The
sequence and type of amino acids as well as their bonding in the
protein chains partly contribute to the overall properties of the
resulting fibers (Choudhury, 2006). The presence of amino group
and carboxylic group in the protein molecule (Scheme 9) renders
the ionic nature of protein polymer. However, the acidic and basic
characteristics of protein fiber are pH dependent while its iso-
electric point is around pH 5.5 (Scheme 10) (Broadbent, 2001).
Under acidic conditions, protein molecules form the protonated
amino group (NHþ 3 ) which can easily attract the anionic dye mol-
ecules like acid dye and also lawsone anions towards the fiber
(Amro et al., 1993). The affinity of a rather small molecule is mainly
attributed to an ionedipole interaction between the polar groups of
the henna dye and protonated amino groups of the wool, which
help fix the dye firmly to the fiber (Bechtold and Mussak, 2009). The
ionizing properties of lawsone and keratin can be predicted from
Table 3.
The red-orange component of henna dye which is substantive
towards keratin produces a deep shade during dyeing with wool
fiber (James et al., 1986). The dyeing of wool fiber with henna dye
can be carried out by mordanting and without mordanting
methods in acid medium and the maximum exhaustion of dye is
found at pH-3 (Bechtold and Mussak, 2009). The mordanting of
wool fiber was executed using various metal mordants such as tin
chloride, ferrous sulfate, potash alum and also non-metal mordant
like chitosan (Zhao et al., 2007; Yusuf et al., 2012, 2015; Dev et al.,
2009). The experimental observation showed that the depth of
shade and color strength (K/S value) of mordanted dyed samples is
higher than un-mordanted dyed samples for the similar shade
percentages (Table 4). However, the effect of non-metallic mordant
(chitosan) on the color strength of henna-dyed wool fiber is more
pronounced compared to metal mordants. The improvement in
color absorption of wool fibers due to chitosan treatment is asso-
ciated with the introduction of primary amino groups into the fiber
structure (Dev et al., 2009). As far as colorfastness is concerned, the
dyed samples with and without mordanting exhibited an almost
similar fastness ratings in terms of washing, rubbing and perspi-
ration (Yusuf et al., 2015).
Again for silk fiber, the dyeing mechanism with henna dye not
only affected by the presence of free amino and carboxylic acid
groups but also by phenolic eOH group (Uddin and Hossain, 2010).
In addition, like wool fiber silk can be dyed without mordanting
and mordanting methods such as pre-mordanting, simultaneous
mordanting and post-mordanting (Li et al., 2011). Copper sulfate,
ferrous sulfate, aluminum potassium sulfate, rare earth elements
and acetic acid are the common mordants being employed for
h mordanting of silk fiber (Ramasubramanium et al., 2016). But
78.04 among all the mordants, potash alum turns out to be the most eco-
73.10 friendly, cheap and readily available mordanting agent for the
74.32 treatment of silk fiber (Samanta and Konar, 2011). The effect of
31.90 mordants on the dye absorption of silk fiber is similar to that of
35.54
wool fiber. But only the hue and the characteristics of the color of
 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22 19

CH3 CH3

H2C CH CH2 N CH3 + NaOH H2C CH CH2 N CH3 + NaCl + H2O

O
Cl OH CH3 CH3
EP3MAC
CHPTMAC

CH2OH OH

CH O CH3
O CH CH

HC OH HC HC CH + H2C CH CH2 N CH3

OH
OH O
O CH CH HC O CH3
EP3MAC
OH CH2OH

OH-

CH2OH OH

CH O O CH CH

HC OH HC HC CH
OH
OH
O CH CH HC O

OH CH2OCH2CH(OH)CH2N+(CH3)3
Cationised cotton

Scheme 8. Reactions that occur during the cationization process of a cotton fabric (Omer et al., 2015).

Table 3
NH2 CH CONH CH CONH CH COOH Distribution of charged species in keratin and lawsone at various pH values (Amro
et al., 1993).
R R* amidic R** pH
group
3 4 5 6 7 9
Scheme 9. Peptidic chain of a protein polymer.
Percentage of total charged species in keratin
Positively charged 99.95 99.50 95.0 50.0 5.00 0.05
Negatively charged 0.05 0.50 5.0 50.0 95.0 99.95
henna dyed silk fabric are found to change with the type of mor- Percentage of total lawsone molecules
dants being employed (Table 5). Furthermore, the performance of Anion 5.00 50.0 95.0 99.5 99.95 100.0
mordanting agent also varies according to the methods being Undissociated 95.0 50.0 5.0 0.5 0.05 0.0
Relative probability of interaction 100 100 95 50 5 0
applied and a maximum uptake of dye by silk is observed for the
post-mordanting process (Table 6).
The application of mordants on silk fiber not only enhances the
color yield but also improves the fastness properties by forming an 4.3. Nylon fiber
insoluble complex between the dye and the mordant within the
fiber interior leading to a bright and fast colored material (Saxena Nylon, a man-made synthetic fiber of an aliphatic polyamide
and Raja, 2014). Another study (Alam et al., 2007) has shown the polymer nature, is typically interlinked by the amide (eNHeCOe)
effect of electrolyte concentration and temperature on the linkages (Deopura et al., 2008). The recurring amide linkages being
exhaustion of henna dye. The results have revealed that the integral parts of polyamide polymer backbone are formed through
exhaustion of dye increases with the increment of electrolyte polycondensation polymerization. The polymerization reactions
concentration and dyeing temperature (Table 7). It may be assumed suitable for the formation of polyamide are well-documented, and
that an elevated dyeing temperature increases the kinetic energy of the commercially important nylons are obtained by processes
the dye molecules and hence tends to break down large aggregates associated with either of two basic approaches: one involves the
into smaller ones that facilitate an easier diffusion of dye molecules formation of nylon 66 by polymerization of adipic acids and hex-
into the fiber (Chatwal, 2009). amethylenediamines while the other one entails nylon 6 through
ring-opening polymerization of caprolactam (Lewin, 2007).
The most important chemical groups in the nylon polymer are

H3N Wool CO2H H3N Wool CO2- H2N Wool CO2 -

H+ H+
acidic pH<5 isoelectric pH-5.5 alkaline pH>9

Scheme 10. Change in acidic and basic nature of protein fiber with pH change.
20 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22

Table 4
Spectrophotometric characterization of henna dyed samples (Dev et al., 2009).

Dye concentration (% owf) Chitosan concentration (% w/v) K/S Relative color strength (%) L* a* b* DE value
3 Untreated 0.3439 100 57.37 16.82 33.10 e
0.5 0.4707 137 56.44 13.77 32.56 3.23
1.0 0.5341 155 55.24 11.93 32.43 5.37
1.5 0.6218 180 53.63 12.10 31.33 6.27
9 Untreated 0.5726 100 49.97 18.90 36.25 e
0.5 0.7688 134 48.65 14.98 36.01 4.13
1.0 0.8735 153 46.98 14.33 31.44 7.27
1.5 0.8901 156 46.96 13.85 32.32 7.06
15 Untreated 0.8167 100 45.94 17.98 33.59 e
0.5 0.8525 104 45.74 16.95 34.76 1.57
1.0 0.8845 108 45.88 15.96 34.90 2.40
1.5 0.9406 115 44.68 16.62 33.72 1.85

Table 5
Impact of mordant on hue and color characteristics of dyed fabric samples (Li et al.,
2011).

Mordant Color L* a* b* c*
H NH (CH2)5 CO OH
Without mordant Light orange 5.71 2.11 3.01 1.45 n
Iron Black-gray 3.11 9.42 13.24 3.26
Copper Gray-green 3.38 4.74 5.62 5.79 (I)
Alumina Orange 4.06 12.13 16.52 6.29
Rare earth Orange 4.13 13.91 19.78 7.21
H NH (CH2)6 NHCO (CH2)4 CO OH
n
Table 6
Comparison of the K/S values of silk fiber dyed with henna dyestuff using different (II)
mordanting methods (Li et al., 2011).
Scheme 11. Chemical structure of nylon 6 (I) and nylon 66 (II) polymer.
Mordant Pre-mordanting Simultaneous Post-mordanting
K/S value mordanting K/S value K/S value

Without 1.31 1.31 1.31 eucalyptus wood, curcumin and saffron (Rossi et al., 2015; Arora
mordant
Iron 3.32 3.38 4.22
et al., 2012; Lokhande and Dorugade, 1999). In addition, nylon
Copper 2.98 3.45 5.09 can be dyed with the extracts of henna through a dyeing mecha-
Alumina 4.06 3.21 5.60 nism of acid dye by cationic amino groups (Badri and Burkinshaw,
Rare earth 1.97 2.67 5.76 1993). As discussed earlier, lawsone is weakly acidic by nature
which may exhibit substantivity towards cationic sites of nylon fi-
ber through an ionic interaction.
Table 7 Mirjalilia et al. (2014) have applied henna dyes on nylon fabric
Effect of electrolyte concentration and temperature on exhaustion (%) of henna dye
after treating the fiber with three different mordants such as potash
by silk fiber (Alam et al., 2007).
alum, cupric sulfate and ferric sulfate. It has been observed that
No. of Electrolyte Dye Dyeing Dye mordanted dyed samples exhibited a higher color strength
experiment concentration (%) exhaustion temperature ( C) exhaustion
compared to unmordanted samples especially in case of ferric
(%) (%)
sulfate as mordant. Again, Badri and Burkinshaw (1993) studied
1 0 32 30 37 colorimetric and fastness properties of dyed nylon fabric with
2 2 34 40 34
3 4 71 50 72
henna extract after being chromed with potassium dichromate. The
4 6 79 60 85 results showed that prechromed mordanted dyes on nylon forms a
5 8 79 70 90 dye-metal complex which characteristically imparts an enhanced
6 10 90 80 93 fastness to light and washing and also causes dulling of the shade. It
7 12 90 90 93
is worth noting that lawsone may chelate chromium which in turn
leads to an increased colorfastness of the dyes on the nylon fiber
under consideration.

the polar amide group (eCOeNHe) in the polymer backbone, and

the amino groups (eNH2) found at the ends of the polymer chains
(Scheme 11). The polar nature of amide group causes swelling of
nylon fibers in water or in polar solvents while the presence of a
ketonic oxygen atom causes an increased absorption of dyes by
fiber during dyeing. Again, the cationic sites are the terminal amino
groups which are protonated by acid to form cationic (NHþ 3 ), and
this presents favorable sites for dyeing property with synthetic
dyestuffs such as acid as well as pre-metallized dyes in dye liquor at
a lower pH (Broadbent, 2001). However, in recent years the color-
ation of nylon fibers has been studied with natural dyes from
various natural resources such as onion, lac, turmeric, madder,
4.4. Polyester fiber
Polyester is the general name given to the fibers usually made
from polyethylene terephthalate that contains the ester functional
group in its main chain and is formed through the poly-
condensation reaction of a glycol (or diol) with a difunctional car-
boxylic acid (or diacid) (Edlund and Albertsson, 2003). The
presence of two functional groups in both reacting components
results in the formation of a linear polyester molecule. Polyesters
are of great importance as fiber materials in terms of volume and
product value due to their versatility in the various application
 M.A.R. Bhuiyan et al. / Journal of Cleaner Production 167 (2017) 14e22
Scheme 12. Chemical structure of polyethylene terephthalate (PET).
sectors with a relatively low raw materials and production costs
(Scheirs and Long, 2005). Among all the classes of polyester fiber,
the most commercially important and long established fiber ma-
terial is polyethylene terephthalate (PET) which is an aliphatic-
aromatic polymer (Scheme 12) consisting of terephthalic acid
(TPA) and ethylene glycol (EG) (Deopura et al., 2008). The large
molecules along with inflexible structure of PET macromolecules
lead to a compact and highly crystalline molecular arrangement of
polyester fiber associated with a high melting point likewise glass
transition temperatures as well as its insensitivity to moisture and
various chemicals (Lewin, 2007).
The highly crystalline structure and a lack of polarity make
polyester fiber hydrophobic in nature (El-Nagar et al., 2006) that
resists the entry of water molecules into the polymer system
leading to a limited swelling in water at lower temperature. Like-
wise, the hydrophobicity of polyester fiber restricts any diffusion of
dye molecules into the fiber interior during dyeing (Peters and
Ingamells, 1973) which in turn makes its dyeing process exceed-
ingly difficult with most of the commercial synthetic dyestuffs
except the disperse dyes (Owis, 2010). At a high temperature and
pressure, polyester can be dyed with disperse dye owing to its very
small particle size and non-ionic nature (Gohl and Vilensky, 1983).
An elevated temperature and pressure employed in dyeing may
open up the pores of polyester polymer allowing minute dye par-
ticles to penetrate deep into the fiber interior (Broadbent, 2001).
To surmount the barrier of hydrophobicity, polyester fibers are
pretreated with plasma, ozone, mordant and alkalis for the color-
ation with natural dyes (Purwar, 2016). Several studies (Ado et al.,
2015; Shahin et al., 2014; El-Nagar et al., 2014) have been con-
ducted on the dyeing of pretreated polyester fiber with natural
colorants such as onion, madder, saffron, kola nut, dolu and cur-
cumin. However, a systematic investigation and application of
henna dye on polyester fiber are inadequate despite its well-
established use as a dye for natural fibers. Singh et al. (2006)
have introduced a high temperature (130  C) for dyeing of poly-
ester fabric with henna dye under a closed dyeing system. The
saturation dye uptake i.e. a near complete exhaustion of dye from
dyebaths was observed due to a high temperature dyeing. Again,
the colorimetric data of most dyed samples lie between þ a*
(redness) and þ b* (yellowness) values which revealed the char-
acteristic orange to pale yellow color of polyester fabric dyed with
henna dye. Another research compared the dyeing performance of
100% polyester, 100% cotton and cotton-polyester (35%/65%)
blended fabric with henna dye at 100  C in presence of sodium
chloride along with copper sulfate as a mordant (Owis, 2010). The
study reported that color strength i.e. K/S value of the dyed poly-
ester fabric is much lower (1.81) compared to cotton (8.70) and
blended fabric (2.75). However, henna-dyed polyester fabric
demonstrated an excellent colorfastness property against washing,
perspiration and light than other dyed fabrics. The excellent
colorfastness properties against washing and perspiration
demonstrated by polyester fiber dyed with henna may be attrib-
uted to its highly crystalline structure and hydrophobic nature. The
high crystallinity can help entrap the dye molecules inside the fiber
strongly while hydrophobicity restricts the entry of water
21
molecules into the polymer system and also provides a limited
swelling during washing for removal of excess dye molecules from
the fiber interior.
5. Conclusions
Lawsone being structurally similar to naphthalene is the major
bioactive constituent of henna leaf which acts a source of coloration
for skin and hair of humans since a primitive age. Thanks to bur-
geoning environmental concerns and a growing awareness that
have engendered a renewed interest in expanding its scope and
applications in the coloration of textile fibers with some successes
and promises. Thus, this review article has been mainly focused on
the applications of henna in textile coloration with the compilation
of all the available information regarding the constitutional and
chromatic properties in line with its ionic nature. Due to the
presence of polar groups, henna shows an acidic nature through
proton releasing capability which promotes its use in the textile
dyeing process. The resemblance of this particular nature with that
of cellulosic fiber suppresses its affinity and as a result, an addi-
tional treatment involving mordanting or surface treatment is
required along with different chemicals in various applied
methods. On the other hand, the difference in this nature among
henna, protein and polyamide fibers facilitates its binding leading
to an excellent fastness property along with an increased color
intensity. Despite being ionic by nature, textile coloration with
henna can be achieved even for hydrophobic fibers at an elevated
temperature that imparts excellent colorfastness properties against
washing, perspiration and light with of course, a limited color
intensity.
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