Bioresource Technology 81 (2002) 171177

Process balance and product quality in the production of natural

indigo from Polygonum tinctorium Ait. applying
low-technology methods
a,*
T. Bechtold , A. Turcanu a, S. Geissler b, E. Ganglberger b

a
Institute for Textile Chemistry and Textile Physics, LeopoldFranzens-University Innsbruck, Hoechsterstrasse 73, A-6850 Dornbirn, Austria
b
Institute for Applied Ecology, Seidengasse 13, A-1070 Vienna, Austria
Received 30 July 2001; received in revised form 5 August 2001; accepted 16 August 2001

Abstract
Indigo is the most important blue component in the class of natural dyes for cellulose and protein bres. In the moderate
European climate Polygonum tinctorium Ait. could be an interesting source for natural indigo (Vat blue 1). Following a cultivation
of the plant material a simple procedure for the extraction of the indigo precursor indican was investigated with regard to crop and
quality of dye obtained. The dependence of the crop on the storage conditions of the harvested plant material was investigated. The
results quantify the distinct sensitivity of the fresh material to the time of storage before extraction with regard to the amount of
natural indigo obtained, the photometrically determined indigo content in the product and the shade and colour depth observed in
standardised dyeing experiments. A basic set of data is presented, which describes the process in terms of consumption of energy,
water and chemicals and organic waste released from the extraction step. 2001 Elsevier Science Ltd. All rights reserved.

Keywords: Indigo; Natural dye; Textiles; Dyeing; Indican; Polygonum tinctorium Ait.; Dyer's Knotweed; Colour

1. Introduction Due to the importance of indigo considerable re-

For textile dyeing with natural dyes, indigo has an
almost unique position as the most important blue
natural dye (CI Vat Blue 1). Woad (Isatis tinctoria L.)
and Dyer's Knotweed (Polygonum tinctorium Ait.) were
cultivated in Europe for the production of indigo up to
the 17th century. After this time indigo from the Indigo-
plant (Indigofera tinctoria L.) was used because of the
superior quality of the dyestu (Schmidt, 1997). At the
end of the 19th century the synthetic indigo almost
completely displaced natural indigo. In 1913 the pro-
duction of synthetic indigo had reached more than
33,000 tons (Schweppe, 1993). At this time mainly
woollen clothes were dyed for marine blue textiles with
excellent fastness properties.
At present the main market for indigo is dyeing of
cotton yarn for the production of denim (Essl, 1999,
2000a,b). The annual production of synthetic indigo is
estimated as 22,000 tons of dyestu (Schrott, 2001).
*
Corresponding author. Tel.: +43-5572-28533; fax: +43-5572-28629.
E-mail address: textilchemie@uibk.ac.at (T. Bechtold).
search has been performed to replace the chemical
synthesis of the dye by an application of biotechnolog-
ical methods (O'Connor and Hartmans, 1998; Itoh
et al., 1999; Bhushan et al., 2000; Young-Am et al.,
2000; Shim et al., 1998). At present there is still con-
siderable demand for research to optimise these methods
of biosynthesis with regard to their production costs
(Schrott and Saling, 2000).
For the production of eco-textiles based on natural
dyes an evaluation of economic and ecologic sources for
natural dyes is of growing interest (Geissler and
Ganglberger, 2001). Yellow, red, brown, green and dark
grey shades can be obtained from various sources of
plant material e.g. buds from Canadian Golden Rod,
Madder roots, barks from Sticky Alder tree, Ash-tree
(Bechtold et al., 2001). Despite the various shades that
can be obtained with such dyes the need for indigo as a
blue component is persistent.
As a result, with the historical disappearance of in-
digo farming in Europe there is a considerable lack in
knowledge with regard to simple production of natural
indigo from plant material with consideration of the
ecological standards applied at present. For an ecient

0960-8524/02/$ - see front matter 2001 Elsevier Science Ltd. All rights reserved.
PII: S 0 9 6 0 - 8 5 2 4 ( 0 1 ) 0 0 1 4 6 - 8
172 T. Bechtold et al. / Bioresource Technology 81 (2002) 171177

and ecological production of natural indigo a simple
extraction method is required (Th uringer Landesanstalt,
1999). From the historical literature it is known that the
freshly harvested plant material containing the indigo
precursors e.g. Isatan B (Indoxyl-5-ketogluconat, Isatis
tinctoria L.) or indican (Indoxy-b-D -glucosid, Poly-
gonum tinctorium Ait.) exhibits a distinct sensitivity on
the conditions of storage and extraction (Schweppe,
1993). Detailed information about the time dependence
of the crop of indigo is needed as a basis to optimise
harvesting, storage of plant material, extraction of in-
digo precursors and dye formation.
In many papers dealing with the production of indigo
from natural sources the amount of indigo formed was
determined by analysis of precursor substances e.g. in-
dican or indoxyl or by chemical extraction methods
(O'Connor and Hartmans, 1998; Itoh et al., 1999;
Young-Am et al., 2000; Shim et al., 1998). For an
evaluation of the overall crop of indigo the formation of
indigo dye should be considered because losses during
the (bio)chemical transformation of the precursors of
the dye have to be considered.
In this study Dyers' Knotweed (Polygonum tinctorium
Ait.) was chosen as a representative plant for further
investigation.
A simple standard procedure, considering both basic
technical equipment available to a farmer at moderate
costs and ecological demands of a dyestu extraction, is
presented. Results of an experimental study to deter-
mine the inuence of the storage and the conditions of
indican extraction on the total amount of indigo ob-
tained per kg plant material and on the dyestu content
in the dried product are given. The crude indigo dye
obtained with the proposed extraction method was
analysed for its indigo content by spectrophotometry
and in addition standard dyeings were performed to
dene the obtained shade and colour depth in compar-
ison to synthetic indigo. The given results form a basic
set of data required for optimisation and further scale
up of the extraction process, including methods for
standardisation and quality control of the product.
2. Methods
2.1. Plant material
The seed material for Polygonum tinctorium Ait. was
obtained from the Th uringer Landesanstalt f
ur Land-
wirtschaft Jena (Dornburg, Germany). Cultivation was
performed in the moderate climate of Vorarlberg
(Austria) during the summer period of 2000. The plant
material was harvested in the end of September 2000 to
avoid damage of plants by possible frost during nights.
The total mass (leaves and stem) of wet plant material
was approximately 250 kg. To study the inuence of
storage conditions the material was separated within
24 h after harvesting into samples of 1520 kg mass. The
sample identication and storage conditions are shown
in Table 1. After a dened storage time the samples were
extracted with application of a simple standard proce-
dure (Fig. 1).
Storage at room temperature was chosen as a general
method. To estimate dierent strategies for longer
storage, two samples were air dried with absence of di-
rect sunlight (Samples 12, 13, Table 1) one sample was
stored frozen (14) and one sample was stored in water
(11).

Table 1
Sample characteristics: storage conditions, pH and redox potential (E) at the end of indican hydrolysis, absolute amount of crude dyestu and crude
dye calculated per 100 kg plant material
Sample Storage Indican hydrolysis Mass
Time Temperature pH E Plant material Crude dye Crude dye/100 kg
(d) (C) (mV) extracted (kg) (g) plant material (kg)
1 0.7 ca. 20 4.35 70 7.7 31.4 0.44
2 1 ca. 20 3.99 )80 17.8 95.6 0.54
3 1 ca. 20 4.23 )80 7.2 55.3 0.79
4 2 ca. 20 4.00 )20 19.2 53.2 0.28
5 4 ca. 20 3.85 )170 18.5 19.8 0.11
6 5 ca. 20 3.87 )180 16.8 16.4 0.10
7 6 ca. 20 3.89 )150 15.1 45.2 0.30
8 7 ca. 20 4.04 )80 17.1 55.5 0.32
9 8 ca. 20 4.07 )190 20.8 101.1 0.49
10 9 ca. 20 n.d. n.d. 20.3 69.9 0.34
11 49 ca. 20 4.36 50 20 259.2 1.30
12 49 1015 4.59 )120 18.9 40.2 0.21
13 53 1015 4.56 )70 16.9 18.1 0.11
14 54 < 20 3.73 )50 17.0 20.2 0.12
15 3a ca. 10 4.16 20 2 12.9 0.64
a
Samples 114: cultivation in Batschuns (660 m over sea level) and Tufers (520 m), hills, soil Braunerde; sample 15: cultivation approx. 6 weeks later
in Hohenems, (410 m), at valley, soil: river sediment.
 T. Bechtold et al. / Bioresource Technology 81 (2002) 171177
Fig. 1. Production scheme for a basic process for natural indigo.
2.2. Extraction of indican and formation of crude indigo
An amount of 1520 kg of plant material was ex-
tracted in two stages with soft water (<20 ppm Ca2 ).
The rst extraction step was performed for 4 h with a
volume 40 l at 5070 C, followed by a second extraction
for 2 h with 20 l water at 40 C. The combined extracts
were stored for 45 days in open polyethylene contain-
ers. During this time the solution was stirred for some
minutes per day to introduce air oxygen.
pH and redox potential of the solution were mea-
sured at the end of the storage period by means of a
glass electrode and a Pt-electrode, respectively (Ag/
AgCl, 3M KCl reference, Orion 720 A, Orion Research,
Boston, MA). To improve occulation and precipitation
of indigo approx. 1:5 g=l CaCl2
2H2 O (technical grade)
was added before ltration. The sediment was collected
and ltered through a cotton fabric. After drying in a
laboratory dryer at 70 C the amount of crude indigo
was weighed. The material then was pulverised and used
in dyeing experiments and for analytical tests.
2.3. Analytical determination of indigo
The indigo content in the crude dyestu was deter-
mined by photometry (Bechtold et al., 1992; Merritt
et al., 2001). An aqueous alkaline solution of Fe(II)tri-
ethanolamine was used as reducing agent. In a 100 ml
volumetric ask 0.1 g of pulverised crude dyestu was
173
dispersed in 20 ml of a solution containing 33 g/l NaOH,
333 g/l triethanolamine (85% o.w.), 50 g=l FeSO4
7H2 O
and 0.8 g/l citric acid. The ask then was lled to 100 ml
with a solution containing 10 g/l NaOH, 50 g/l trietha-
nolamine (85% o.w.) and 5 g=l FeSO4
7H2 O. To com-
plete reductive extraction and dissolution of the dyestu
the solution was held at 40 C for 60 min with gentle
shaking every 15 min. The spectrum of the solution was
recorded from 350 to 700 nm using a diode-array
spectraphotometer (Zeiss CLH 500/MCS521 UVVis,
Carl Zeiss (Jena) Germany, 1 mm cuvette). For the de-
termination of the content of indigo the absorbance at
410 nm was used. Synthetic indigo (Indigo Plv. DyStar,
Frankfurt a. Main, Germany) was used as a standard
dyestu for calibration.
P.a. quality NaOH was used, FeSO4
7H2 O,
Fe2 SO4 3
78H2 O, CaCl2
2H2 O, triethanolamine, ci-
tric acid, and Na2 S2 O4 were technical grade chemicals.
2.4. Determination of the colour strength
The colourimetric determination of the colour
strength of the natural dye was determined in a series of
standardised exhaust dyeing experiments (Mathis Lab-
omat BFA-8, Mathis AG Niederhasli, Z urich, Switzer-
land). Depending on the estimated indigo content of the
product, an amount of 225 g dyestu was pulverised
and brought to 100 ml with a solution containing
10 g=l Na2 S2 O4 , 80 ml/l NaOH 50% and 1 g/l dispersing
174 T. Bechtold et al. / Bioresource Technology 81 (2002) 171177
agent (lignosulfonate, Setamol WS, BASF, Ludwigsha-
fen, Germany). Complete reduction was achieved by
gently shaking the solution for 1218 h at 40 C. A
volume of 20 ml of this stock vat was then used for a
dyeing experiment: 10 g of bleached cotton fabric were
dyed in a liquor ratio of 1:10. 5 g=l Na2 S2 O4 , 7 ml/l
NaOH 50%, 10 g=l Na2 SO4 and 1 g/l dispersing agent
(Setamol WS) were added to the dyebath. Within 20 min
the dyebath temperature was raised to 60 C and
maintained at 60 C for 45 C. To compensate for the
low substantivity of indigo the dyebath was cooled to
25 C before removal of the samples. Additional liquor
was removed by squeezing the samples with a laboratory
padder followed by air oxidation for at least 1 h. After
complete oxidation the samples were rinsed in water and
neutralised in a bath containing 1 ml/l acetic acid (80%).
Drying of the samples was performed at 80 C in a
laboratory drying unit (Mathis Labdryer, Mathis AG,
Niederhasli, Zurich, Switzerland). The CIELab coordi-
nates of the dyeings were measured with a tristimulus
colorimeter (Minolta Chroma-meter CR 210, sample
diameter 50 mm, D65). The indigo content was deter-
mined according to the KubelkaMunk function, the
K=S values were calculated from the reectance deter-
mined at 660 nm (Pye Unicam SP 8100 double beam
spectrophotometer, diuse reectance sphere 0/d).
Standardisation was performed with Indigo Plv.
(DyStar) using identical procedures for dyestu reduc-
tion and dyeing.
3. Results and discussion
The analysis of the indigo concentration in the crude
dyestu obtained was performed by photometry and by
standardised dyeing experiments. Assuming an equal
content of indican in the plant material, the amount of
crude indigo used for the dyeing experiments was in-
creased in proportion to the amount of crude product
obtained per kg of extracted plants. The natural dyeings
were compared to standard dyeings obtained with
Indigo Plv. BASF (Exp. 16 1% and exp. 17 3% in col-
our depth). From a set of standard dyeings the colour
depth was determined for dyeings 115 according to
the KubelkaMunk function. The results of the in-
digo content as function of storage time are given in
Table 2.
As shown in Table 2 the mass of crude dyestu and
the indigo content were directly dependent on the time
of storage. A dramatic decrease in colour strength and
indigo content of the products within 23 days of stor-
age at RT was observed. During the rst two days of
storage at room temperature the extractable amount of
indigo decreased from 50 g/100 kg (expts. 1, 3) to 9 g/100
kg (expt. 4). After a storage time of more than 4 days the
extractable indigo content generally dropped to less than
3 g/100 kg. Only sample 9 showed a remarkable content
of indigo after a storage period of 8 days. In this sample
the photometrically determined indigo content seemed
to exceed the results found in the dyeing experiments,
which can be explained by an increased content of ex-
tractable yellow components. A subtraction of the light
absorption of coloured by-products extracted was not
attempted because in alkaline medium a partial reduc-
tion of the indigo is also possible, due to reducing
components present in the crude product.
Sample 15 was harvested from a dierent site of
cultivation so the initial indican content was dierent.
The material was stored outside for 72 h at 510 C.
Despite the longer duration of storage a remarkably
higher indigo content was found, indicating that a re-
duction in temperature permits prolongation of storage
before extraction.
On the basis of the analytical data and from the re-
sults of the dyeing experiments both the indigo content
in the crude dyestu and the crop of dye per 100 kg
plant material were calculated (Table 2). In the purest
samples an indigo content of approximately 10% was
determined. Related to the total mass of wet plant ma-
terial up to 70 g indigo were obtained per 100 kg of
plants, which corresponds to an indigo content of
0.070%.
In experiments 12 and 13 the material had been air
dried before extraction. In experiment 12, 3.36 kg air dry
material was obtained from 16.9 kg of plant matter and
in experiment 13, 3.50 kg was obtained after drying
starting from 18.9 kg material. Considering a water
content of 80.8% the indigo content in the dry material
can be given as 0.35%. In some historical reports only
the leaves were used for the extraction which would
require an additional separation step to remove the
stems. The stems represent approximately 50% of the
total mass, so results given in such reports tend to higher
values of indigo content (Schweppe, 1993).
The tendency of the analytical determination of the
indigo content corresponds to the ndings from the
dyeing results. The dierence in the calculated indigo
content between the two dierent methods can be ex-
plained with the dierent methods for dyestu extrac-
tion and applied instrumental methodology.
Besides the colour strength the shade of the dyeings
are of particular interest to determine changes in the
dyeing results as a function of the conditions of dyestu
preparation particularly with regard to the storage of
the plant material.
In comparison to the standard dyeings shown in
Table 2, dyeings with natural indigo tended towards
more greenish shades which can be seen in the more
negative a-values. Sample 2 shows only minimal dier-
ences of Lab-coordinates compared to the standard
dyeings, indicating that a good quality of dye can be
obtained without further purication. The CIELab-
 T. Bechtold et al. / Bioresource Technology 81 (2002) 171177 175

Table 2
Indigo content in the samples determined by photometry and standard dyeing experiments calculated as crop pure natural indigo per 100 kg plant
material, K=S values of the dyeings (KubelkaMunk value at 660 nm) and Lab-coordinates (CIELab colour coordinates) of the dyeings obtained
Sample Photometry Dyeing
Purity Indigo per K=S L a b Purity Indigo per
(%) 100 kg (g) (%) 100 kg (g)
1 9.2 40.0 10.1 28.22 )2.81 )14.84 12.3 53.6
10.9 27.22 )2.73 )15.11
2 2.1 11.3 8.3 28.75 1.17 )20.29 4.2 22.4
8.3 29.46 1.04 )20.39
3 2.5 19.9 13.3 27.23 )1.76 )17.33 6.29 49.9
13.3 27.03 )1.92 )16.92
4 3.5 8.4 4.5 39.28 )4.36 )16.67 3.2 9.0
4.4 39.29 )4.34 )16.96
5 2.4 2.5 1.1 56.91 )5.22 )13.60 1.4 1.4
1.2 56.54 )5.24 )13.69
6 <2.0 0.5 65.77 )4.52 )10.35 0.6 <1.0
0.5 65.77 )4.52 )10.35
7 <2.0 1.0 57.28 )4.78 )12.28 0.5 1.5
1.1 56.97 )4.70 )12.50
8 <2.0 2.1 50.49 )4.22 )18.12 1.0 3.3
2.0 50.97 )4.19 )17.71
9 3.5 17.0 4.9 37.90 )5.19 )16.49 2.1 10.0
4.7 38.36 )4.97 )16.41
10 2.0 6.9 1.6 52.61 )6.03 )13.04 0.7 2.4
1.6 53.34 )6.23 )12.62
11 <2.0 0.9 56.88 )4.83 )5.12 0.2 3.0
1.2 53.21 )5.47 )5.20
12 <2.0 0.4 69.01 )5.76 )8.35 0.0 <1.0
0.4 69.17 )5.51 )9.34
13 <2.0 0.2 78.03 )7.40 )4.78 2.2 2.4
0.2 77.45 )6.96 )4.48
14 <2.0 0.2 78.76 )7.11 )6.65 1.9 2.3
0.1 78.46 )7.60 )7.09
15 6.2 39.9 7.1 33.17 )4.45 )15.82 10.8 69.4
7.1 32.44 )4.27 )15.85
16 4.3 40.91 )1.74 )22.52
Indigo 1% 4.0 42.72 )2.04 )21.64
17% 8.1 30.85 0.30 )21.59
Indigo 3% 8.1 30.29 0.50 )21.65

coordinates are in good agreement to the data given for
dyeings with synthetic indigo (Bechtold et al., 1997; Xin
et al., 2000).
The observed decrease in dyestu content in the
products was accompanied by a distinct shift in shade
towards yellow/green. The photometric curves given in
Fig. 2 also prove this nding. The spectra of the natural
dyes samples 1, 9, 15 show higher absorption at wave-
lengths above 440 nm indicating an increased content of
yellowbrown components.
For comparison the spectra of the Fe(II)triethanol-
amine complex solution and of the corresponding
Fe(III)-complex also are shown in Fig. 2.

4. Summary

The extraction of the plant material was performed as

Fig. 2. Absorption spectra: indigo samples 1, 9, 15 (see Table 1),
standards 0.05 and 0.1 g/l indigo in Fe(II)triethanolamine complex
solution and spectra of the Fe(III)-form and the Fe(II)-form of the
complexes.
a simple hot water extraction to dene a simple basic
technology which could be handled by a farmer imme-
diately after harvesting.
A production scheme for the extraction of indigo
precursors from Dyer's Knotweed and the following up
176 T. Bechtold et al. / Bioresource Technology 81 (2002) 171177

treatment to form indigo is shown in Fig. 1, important
data for water consumption, energy and chemicals used
and for the required storage volume for a certain pro-
duction capacity are given in Table 3.
For an estimation of the indigo crop the technique of
harvesting and extraction of the plant material has to be
considered very carefully because the amount of indigo
nally obtained for a given indigo content directly is
inuenced by these steps. An optimisation of the farm-
ing conditions will increase the overall amount of indigo
obtained at the end of the treatment, but the relation of
the data for energy, chemicals and water consumption
for the treatment of a certain amount of plant material
will remain constant and be mainly independent of the
indigo content of the plant.
The data in Table 3 indicate several important factors
of the process:
The rapid decrease in the amount of indigo deter-
mined in the product proves the importance of per-
forming the extraction in a short time after
harvesting the plant material.
The estimated energy consumption for the process is
mainly determined by the hot water extraction. For a
scale-up the extraction at lower temperature should
be considered to optimise the energy consumption
of the process. As a rather high volume of water
has to be used an extraction in cold water would be
of particular interest.
Optimisation of the water consumption in the process
by appropriate recycling techniques will be of partic-
ular interest.
Identifying the extraction as an essential step with re-
gard to the amount and quality of the dyestu, a
semi-continuous harvesting/extraction is favourable
because an intermediate storage should be avoided.
In this case the volume of extract to be handled dur-
ing hydrolysis of indican and indigo formation has to
be optimised with regard to the very large volume of
liquid that has to be stored during this period.
After formation of indigo during the hydrolysis, an
addition of CaCl2 facilitates precipitation and speeds up
ltration of the solids.
The addition of chemicals during extraction has to be
avoided because of the contamination of the plant res-
idue, which represents the major part of the organic
mass which has to be disposed o and to avoid any
further treatment of the wastewater released from the
precipitation/ltration step.
The extraction has to concentrate on soluble pre-
cursors e.g. indican. Losses during storage can be ex-
plained by formation of indoxyl and irreversible
oxidation of indoxyl to isatin but also can be caused by
formation of insoluble indigo. Indigo formation is ob-
served following mechanical damage of leaves. In case
of indigo formation an extraction by use of solvents or
reducing chemicals (NaOH, Na2 S2 O4 ) is theoretically
possible, but it has to be excluded because of the
amount of chemicals released with the extracted residue
and because of expected chemical consumption per kg
dyestu.
The results of the dyeing experiments indicate that
the shade of the natural dye tends towards more
greenish shades and a careful standardisation of the
production process will be required to obtain a constant
quality of the natural dye.
Data describing indigo formation on the basis of
analytical results obtained with precursors should be
treated with great care because these values describe a
theoretical maximum content and will be too optimistic
in many cases.

Table 3
Production scheme and basic requirements for daily processing of 100, 1670 and 167,000 kg/d freshly harvested plant material, corresponding to a
production capacity of 0.060, 1, and for 100 kg/d natural indigo from Polygonum tinctorium Ait.
Process step Production capacity of indigo per day
0.060 kg/d 1.0 kg/d 100 kg/d
Harvesting of fresh plant material per day (kg/d) 100 1670 167,000
60 C extraction of (Indican)
Water consumption per day (m3 =d) 0.3 5 500
Energy consumption per day (k W h/d) 14 5230 23,000
Residue for disposal per day (kg/d) ca. 100 ca. 1700 ca. 170,000
Hydrolysis of Indoxyl to form Indigo required storage volume (m3 ) 1.2 20.0 2000
Precipitation of indigo
Waste water released per day (m3 =d) 0.3 5.0 500
Chemicals consumption per day (CaCl2 ) (kg/d) 0.45 7.5 750
Filtration: amount of wet lter cake formed per day (kg/d) 3 50.0 5000
Drying: energy consumption per day (k W h/d) 3 50 5000
Crop of crude dye per day (kg/d) 0.60 10.0 1000
 T. Bechtold et al. / Bioresource Technology 81 (2002) 171177
For a technical product standardised dyeing experi-
ments should be used, while photometric methods are
favourable for a comparison of the indigo concentration
under well-standardised conditions.
Acknowledgements
The authors are indebted to K. Nenning (School for
agriculture, Hohenems, A), A. Riedmann (School for
gardening, Lebenshilfe, Batschuns, A) for cultivation of
the plant material. Authors thank the Thuringer Land-
esanstalt f
ur Landwirtschaft Jena for providing seed
material of Dyer's Knotweed and DyStar for indigo
dyestu.
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