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Ellagic acid from gallnut (Quercus infectoria): Extraction and determination of its dyeing conditions for natural fibres

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Abstract

The dyestuff of ellagic acid in gallnut (Quercus infectoria) was extracted and used in dyeing of woolen strips, feath-ered-leather and cotton using three types of mordanting methods at various pH values. Selected transition element salts [CuSO 4 5H 2 O, FeSO 4 7H 2 O, ZnSO 4 7H 2 O, Al(NO 3) 3 . 9H 2 O] were used as mordant agent at various pH. The dyed samples with highest fastness were obtained by Cu(II) for all samples except for cotton and by Al(III) for only cotton at pH 8 in the pre-mordanting method. It was also observed that gallnut plant based ellagic acid dyestuff would probably be an important raw material in dyeing process of natural textile fibers. Introduction Natural dyes have high importance in hand made-carpet, kilim and the similar industrial dying applica-tions because of high colour fastness, cheapness, long-term color stability and authentic property. Natu-ral dyes are being produced in the Asian countries (Turkey, Iran, India, Azerbaijani), and the products of natural dyes are being used in the most countries of the world. Gallnut (Quercus infectoria) contains the mixture (60-70%) of gallotannin, ellagic acid, starch and glu-cose 1 . The dyestuff in the tannin of gallnut is ellagic acid 2 , which exhibits dyeing properties because of its auxochrome group (-OH) together with other chro-mogen groups. Wool molecules consist of amino acid units, which contain free amino and carboxyl groups 3 . During the dyeing of wool, hydrogen bonds occur between the auxochrome groups of dyestuff and amino groups.
Journal of Scientific & Industrial Research
Vol. 64, July 2005, pp 491-495
Ellagic acid from gallnut (Quercus infectoria): Extraction and determination of
its dyeing conditions for natural fibres
Adem Onal
1
, Ahmet Sari
1
and Mustafa Soylak
2,
*
1
Department of Chemistry, Gaziosmanpasa University, 60240, Tokat, Turkey
2
Department of Chemistry, Erciyes University, 38039, Kayseri, Turkey
Received 03 December 2004; accepted 03 May 2005
The dyestuff of ellagic acid in gallnut (Quercus infectoria) was extracted and used in dyeing of woolen strips, feath-
ered-leather and cotton using three types of mordanting methods at various pH values. Selected transition element salts
[CuSO
4
5H
2
O, FeSO
4
7H
2
O, ZnSO
4
7H
2
O, Al(NO
3
)
3
. 9H
2
O] were used as mordant agent at various pH. The dyed samples
with highest fastness were obtained by Cu(II) for all samples except for cotton and by Al(III) for only cotton at pH 8 in the
pre-mordanting method. It was also observed that gallnut plant based ellagic acid dyestuff would probably be an important
raw material in dyeing process of natural textile fibers.
Keywords: Dyestuffs, Ellagic acid, Gallnut, Natural fibres
IPC Code: D 06 P 1/36
Introduction
Natural dyes have high importance in hand made-
carpet, kilim and the similar industrial dying applica-
tions because of high colour fastness, cheapness,
long-term color stability and authentic property. Natu-
ral dyes are being produced in the Asian countries
(Turkey, Iran, India, Azerbaijani), and the products of
natural dyes are being used in the most countries of
the world.
Gallnut (Quercus infectoria) contains the mixture
(60-70%) of gallotannin, ellagic acid, starch and glu-
cose
1
. The dyestuff in the tannin of gallnut is ellagic
acid
2
, which exhibits dyeing properties because of its
auxochrome group (-OH) together with other chro-
mogen groups. Wool molecules consist of amino acid
units, which contain free amino and carboxyl groups
3
.
During the dyeing of wool, hydrogen bonds occur
between the auxochrome groups of dyestuff and
amino groups.
O
O
HO
HO
O
OH
OH
O
Ellagic acid
No study was available on the dyeing properties of
ellagic acid. So, the present paper is aimed to study
the dyeing properties of ellagic acid for wool, feath-
ered leather and cotton. In order to investigate the
most proper mordant and pH value in terms of the
wash, crock and light fastness in dyeing by ellagic
acid, some selected transition element salts [CuSO
4
5H
2
O, FeSO
4
7H
2
O, ZnSO
4
7H
2
O, Al(NO
3
)
3
9H
2
O]
were used as mordant agent at various pH. Woolen
strips (48), cotton (35), feathered-leather (16) were
dyed using transition element salts as mordant agents.
Materials and Methods
Extraction of Ellagic Acid
Gallnut was picked up from areas of Tokat city,
Turkey. Gallnut cups were dried and powdered. Ex-
traction of the dyestuff was carried out by the
following method
2
: 2 N H
2
SO
4
(1 ml) and powdered
tannin (10 g) are placed into a round-bottomed flask
(2 l) and heated for 24 h at 100°C. After cooling,
pyridine (100 ml) is added and filtered. Sample (1 l) is
mixed with pyridine (1.1 l) in dried flask and HCl
(100 ml) is added and then NaNO
2
(100 ml) is placed
into this mixture at 30°C. The absorbance of the ob-
tained mixture (λ, 538 nm) is recorded by UV-visible
spectrophotometer. Absorbance is recorded after
36 min again. The absorbance change during 36 min
is well proportioned with concentration of ellagic
acid. Consequently, the free ellagic acid (1.6%) is
produced.
——————
*Author for correspondence
E-mail: soylak@erciyes.edu.tr
J SCI IND RES VOL 64 JULY 2005
492
Dyeing of Wool
The dyeing procedures of wool were carried
out using the following three types of mordanting
methods at pH:2, 4, 6, 8 successively for each
mordant:
Pre-Mordanting
White fowl woollen strips (1g) were placed into
0.1 M mordant solution (100 ml) and heated for 1 h at
90
o
C. After cooling, it was rinsed, dried and placed
into 100 ml of dye-bath. After heating for 1 h at
90
o
C, it was allowed to cool. The dyed product was
rinsed with distilled water and dried.
Together Mordanting
0.1 M mordant dyestuff solution (100 ml) and
woollen strips (1g) were placed into 250 ml Erlen-
meyer flask. This mixture was heated for 1 h at 90
o
C.
After cooling, it was filtered, rinsed with distilled wa-
ter and dried.
Last Mordanting
Woollen strips (1g) were heated in dye-bath
(100 ml) for 1 h at 90
o
C. After cooling, the woollen
strips were filtered and dried. Then it was put into 0.1
M mordant solution (100 ml) and heated for 1 h at
90
o
C. Finally, it was filtered, rinsed with distilled wa-
ter and dried.
The dyed-woollen strips, dyed from each of these
three methods, were kept in 3% ammonia solution
(100 ml) to increase the fastness of colours.
Dyeing of Feathered-Leather
Dyeing of feathered-leather process was carried out
using mordanting and together mordanting methods.
The third procedure (Last mordanting) did not give
positive results since the feathered-leather lost its wa-
ter and shrinks at higher temperature (35-40
o
C). The
length of the feather in the feathered lambs-leather
used in this work was 1.5 cm. For these two methods,
the dyeing pH was selected as 2 and 4.
Pre-Mordanting
The white feathered-leather treated with K
2
Cr
2
O
7
(approx 15 cm
2
) was heated for 1 h at 35-40
o
C in
0.1M of mordant solution (100 ml) in a 300 ml Er-
lenmeyer flask. After cooling, it was added into dye-
stuff solution (100 ml) and shaken at frequent inter-
vals for 1 h at 35-40
o
C. After completion of the dye-
ing process, the dyed-feathered-leather was filtered,
rinsed with distilled water and dried.
Together Mordanting
The feathered-leather following pre-mordanting
was added to dyestuff solution (100 ml) and mordant
agents were mixed in 250 ml Erlenmeyer flask. This
mixture was shaken at frequent intervals for 1 h at
35-40
o
C and finally, dyed matter was filtered, rinsed
with distilled water and dried.
Dyeing of Cotton
Cotton has different structure and properties than
wool and leather. It consists of glycoside units and
can occur coordinative and intermolecular hydrogen
bonding with the mordant agent and dyestuff. The
dyeing in cotton was obtained as follows:
Pre-Mordanting
Cotton (1.5g, 50 cm
2
) was heated for 1 h at 95
o
C
in 0.1 M mordant solution (100 ml). After cooling,
the cotton was taken out, rinsed with distilled
water, dried, put into dye-bath (100 ml) and heated for
1h at 95
o
C. It was allowed to cool, then filtered. Fi-
nally, the dyed-cotton was rinsed with distilled water
and dried.
Together Mordanting
Dyestuff solution (100 ml) was added to the cotton
and 0.1 M mordant agent and heated for 1 h at 95
o
C.
After cooling, it was taken out, rinsed with distilled
water and dried.
Last Mordantating
Cotton (1.5g, 50 cm
2
) was dyed in dyestuff solution
(100 ml) for 1 h at 95
o
C. After filtering, it was heated
in 0.1 M mordant solution (100 ml) for 1 h at 95
o
C.
The dyed cotton samples were filtered, rinsed with
distilled water and dried.
Colour codes were determined using Pantone
Colour Guide
4
. The crock, light and wash fast-
ness of dyed samples, which were established
according to DIN 54021, DIN 54004 and to
ISO 105-C06, C1S, respectively
5
, were determined
by a LHTP model Alas Laundero meter, a 255
model crockmeter and a Fadeometer (xenotest),
respectively.
Results and Discussion
The dyeing mechanisms of wool and feathered-
leather with ellagic acid by pre-mordanting (1), to-
gether mordanting (2) and last mordanting (3) can be
considered as follows
6
:
ONAL et al: ELLAGIC ACID FROM GALLNUT FOR DYEING OF NATURAL FIBRES
493
On the other hand, cotton contains cellulose (90%),
which is a linear polymer of 1,3- β-D glucoses as
shown below:
o
o
H
O
o
OH
OH
H
H
H
OH
H
O
H
HO
H
CH
2
O
CH
2
O
Cotton can be dyed without using any mordant
agent. However, when a mordant agent is used in dye-
ing process, a lot of colour tones can be obtained. The
dyeing mechanism of cotton with ellagic acid can be
suggested as below:
o
o
H
O
o
OH
OH
H
H
H
OH
H
O
H
HO
H
CH
2
O
CH
2
O
Me
n +
O
OH
OH
O
O
O
O
O
For wool and feathered-leather, the fastness in-
creases when the pH is varied from 8 to 2 (Fig. 1).
This result means that the dyeing with high fastness
can be achieved in acidic pH range. This is because in
the acidic pH range, the proton of acid is bonded with
free carboxyl group of amino acids in the structure of
wool or feathered-leather and the anion of acid is
bonded to nitrogen atom with positive charge in the
structure
6
. Moreover, in dyeing process by acidic dye-
stuff, the bonding tendency of dyestuff molecule to
the wool decreases in the alkali medium (pH 8). The
dissociation of carboxyl groups increases by the effect
of alkaline and the anion of the dyestuff is to be free
since the positive charged amino acid groups are
bonded to the carboxyl anions. Therefore, the desired
bonding does not occur in the alkaline medium.
The fastness for cotton increases with increase of
pH (Fig. 1). This is because the oxygen atoms in cel-
lulose units of the cotton are free in slightly alkaline
medium and the cellulose units are easily bonded to
the metal cations of mordant agent. The highest fast-
ness (Fig. 2) were obtained by pre-mordanting
method for each of the four metal salts, Cu(II), Zn(II),
Fe(II) and Al(III).
The average fastness values of the all dyed samples
by Cu(II) and Fe(II), respectively, are as follows: Pre-
(1) Wool .....….......Mordant (Me
n+
)......….....Dyestuff
R CH
COOH
NH
2
Me
n+
R CH
C
NH
2
O
O
Me
n+
O
OH
OH
O
O
O
O
O
(2) Dyestuff......…........Mordant (Me
n+
)........….......Wool
Me
n+
O
OH
OH
O
O
O
O
O
RCH
C
NH
2
O
O
(3) Wool......….......Dyestuff (Me
n+
).....….....Mordant
O
O
HO
HO
O
O
O
O
R CH
C
NH
2
O
O
H
Me
n
+
J SCI IND RES VOL 64 JULY 2005
494
Fig. 4—The variation of average fastness for cotton with respect
to the mordant agent
mordanting, 5.75, 4.50; Together mordanting, 5.12,
4.20; and Last mordanting, 4.91, 4.15. The effect of
mordanting agent on the fastness of the investigated
samples can be ordered as Cu(II)>Zn(II)>Al(III)
>Fe(II). This is because the Cu(II) mordanting agent
forms the more stable complex with dyestuff mole-
cules compared to the other mordant.
For dyed feathered-leather samples, fastness values
by Cu(II) are changed from 4.87 to 5.20 and by Fe(II)
mordant agent from 3.5 to 4.10 in pre-mordanting and
together mordanting method, respectively (Fig. 3).
Under average fastness values (wash, crock, light)
of dyed cotton samples by Al(III), Cu(II), Zn(II) and
Fe(II) for the three mordanting methods, the best re-
sult was obtained in presence of Al(III) by together
mordanting method (Fig. 4). The average fastness
values by Fe(II), Al(III), Zn(II) and Cu(II) respec-
tively are as follows: Pre-mordanting, 3.75, 4.30, 4.25
and 3.85; Together mordanting, 4.25, 4.65, 4.30, and
4.45; and, Last mordanting, 3.60, 4.41, 4.0 and 3.80.
Thus, the effect of mordant agent on the fastness of
the cotton samples can be sequenced as Al(III)>
Cu(II) > Zn(II)> Fe(II).
Conclusions
The results show that it is possible to dye natural
fibers using mordanting methods by some transition
metal salts at various pH values. Generally, different
colour and colour tones and excellent fastness dyeings
were obtained with ellagic acid. The highest colour
depths on cotton and protein fibres (wool and feath-
ered-leather) were obtained at 90
o
C for 60 min for
wool and cotton, and at 35
o
-40
o
C for 60 min for
Fig. 1—The variation of fastness with pH
Fig. 2—The variation of average fastness for wool with respect to
the mordant agent
Fig. 3—The variation of average fastness for feathered-leather
with respect to the mordant agent
ONAL et al: ELLAGIC ACID FROM GALLNUT FOR DYEING OF NATURAL FIBRES
495
feathered-leather, because the water of feathered-
leather extracts and shrinks above the 40
o
C. The best
result were obtained using pre-mordanting method for
wool and feathered-leather by Cu(II) mordant salt at
pH4. In addition, the dyed samples with highest
fastness were also obtained by Cu(II) for the samples
except cotton and by Al(III) for only cotton at pH 8 in
the pre-mordanting method. However, a further ex-
perimental study should be made to investigate the
reason for the highest fastness value obtained by
Al(III) for cotton. Consequently, if gallnut (Quercus
infectoria) is used in dyeing process of natural textile
fibres, it will probably be an important raw material
for commercial use.
Acknowledgement
The authors are indebted to the SE-NA textile fac-
tory Tokat, for providing the opportunity to carry out
the fastness analyses.
References
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2 Hagerman A E & Wilson T C, Quantitative determination of
ellagic acid, J Agric Food Chem, 38 (1990) 1678-1683.
3 Onal A & Kepez M, Development of dyeing and colour
properties of buckthorn (Rubia tinctoria) in dyeing wool,
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4 Pantone Textile Color Guide (Pantone Inc., New Jersey)
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Coloration of textiles with natural dyes involves huge consumption of chemicals mainly metal salt mordants, which pose serious environmental challenges. To mitigate this pollution more and more environmentally friendly, biodegradable, biocompatible and renewable products should be popularized in dyeing industry. This paper proposes a sustainable and metal salt free dyeing of wool samples by employing natural mordants extracted from pomegranate peel (Punica granatum L), gallnut (Quercus infectoria L) and catechu (Acacia catechu). The color parameters of dyed wool samples were greatly found to be dependent on the chemical compounds present in respective biomordants and their interaction ability with the functional groups of wool and the dye molecules. The investigated biomordants exhibit different interactions with coloring compounds of Butea monosperma (palas) dye resulting in deep brown, olive green, dark brown, cinnamon, burgundy and yellowish hues on wool. All the biomordants selected in this study improved dye performance and resulted in a broad beautiful spectrum of colors with acceptable fastness properties. The results encourage the search and exploitation of new plant species as source of biomordants to replace metallic and toxic mordants currently used in textile industry.
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Ethnopharmacological relevance Quercus Infectoria galls (QIG) have a long history of use in traditional Chinese medicine and traditional Uyghur medicine for the treatment of diarrhea, hemorrhage, skin disease, and many other human ailments. Medicinal applications of QIG have become increasingly popular in Greece, Asia Minor, Syria, and Iran. Aim of the review The present paper reviewed the ethnopharmacology, phytochemistry, analytical methods, biological activities, metabolism, pharmacokinetics, toxicology, and drug interactions of QIG to assess the ethnopharmacological uses, explore its therapeutic potential, and identify future opportunities for research. Materials and methods Information on QIG was gathered via the Internet (using Google Scholar, Baidu Scholar, Elsevier, ACS, Pubmed, Web of Science, CNKI, and EMBASE) and libraries. Additionally, information was also obtained from local books and PhD and MS dissertations. Results QIG has played an important role in traditional Chinese medicine. The main bioactive metabolites of QIG include tannins, phenolic acids, flavonoids, triterpenoids, and steroids. Scientific studies on the QIG extract and its components have shown its wide range of pharmacological activities, such as cholinesterase- and monoamine oxidase-inhibitory, antitumor, anti-hypertension, antidiabetic, antimicrobial, insecticidal, antiparasitic, antioxidant, and anti-inflammatory. Conclusions The ethnopharmacological, phytochemical, pharmacological, and analytical methods of QIG were highlighted in this review, which provides information for future studies and commercial exploration. QIG has a huge potential for pharmaceutical and nutraceutical applications. Moreover, comprehensive toxicity studies of this plant must be conducted to ensure its safety. Additional investigations are recommended to transmute the ethnopharmacological claims of this plant in folklore medicines into scientific rationale-based information. Research on pharmacokinetics studies and potential drug interactions with standard-of-care medications is still limited, which calls for additional studies particularly on humans. Further assessments and clinical trials should be performed before it can be integrated into medicinal practices.
Article
This part investigates the dyeing properties of myrrh (Commiphora molmol) extract on wool and silk fabrics and the use of eco-friendly materials such as sumac (Rhus coriaria) and manjakani (Quercus infectoria) as mordants. The dyeing conditions (e.g., myrrh concentration, pH, and bath temperature) were optimized. Dyed fabrics were assessed for color strength (K/S), tensile strength, and stiffness. Also, the FTIR for myrrh, sumac, and manjakani was determined. The results show that the best results got in these experiments for dyeing with myrrh extract are: 100% myrrh extract, pH 4.5, temperature 100°C, and the time of 60 min.
Chapter
The reintroduction of colorants from vegetables sources, animals, and minerals is gaining popularity for use in different application fields due to the economical and ecological restrictions imposed by many countries on a number of synthetic colorants that are associated with allergic, toxic, carcinogenic, and harmful responses. Although various sources of natural colorants are known, the tannin colorants from plants are better options to replace or act as co-partners with synthetic dyes in view of their several advantages such as biodegradability and eco-friendliness. Tannins are naturally occurring compounds commonly found in roots, barks, leaves, flowers, skins, fruits, and shells of plants. This chapter discusses the phytoconstituents and coloring compounds in some well-known tannin dye-yielding plants such as cutch, pomegranate, harda, gallnut, and babool, which are grown all around the world.
Article
We have studied the efficiency of analytical procedures for two phenolic compounds found in Eucalyptus globulus and Quercus robur L.: gallic and ellagic acid. Isochratic HPLC was used as a mean of quantitative analysis. Eluants for HPLC analysis were H2O:CH3OH:H3PO4 (975,5:19.5:1, v/v/v) for gallic and (449,5:449,5: 1, v/v/v) for ellagic acid. The time required for each HPLC analysis was 10 and 6 min. The recuperation of gallic acid and ellagic acid was respectively 83,0% and 58,6%. We have showed that high temperature Quercus robur L. kiln drying resulted in an important augmentation in gallic and egallic acid proportions.
Article
A new spectrophotometric method for determining ellagic acid is based on the formation of the quinone oxime of the ellagic acid nitrosylation product. The detection limit of the method is 1 μg of ellagic acid, and the relative standard deviation of the method is 0.8%. The method is selective, with positive reaction from ellagic acid but not from a variety of other common plant phenolics including ellagitannins, gallotannins, proanthocyanidins, phenylpropanoids, flavonoids, and gallic acid. Preparation of hydrolysates of plant samples for analysis of the ellagic acid released from ellagitannins is simple.
HPLC Analysis of ellagic acid in European oak wood (Quercus robur L), Holz Forschum
  • J P Haluk
  • B Churrier
  • M Nargues
Haluk J P, Churrier B & Nargues M, HPLC Analysis of ellagic acid in European oak wood (Quercus robur L), Holz Forschum, 46 (1992) 87-89.