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ACTIVITY BRIEF
Your brief
You need to extract a natural plant dye, then investigate its effectiveness to dye three
different fabrics and write a detailed report of your work. The plant is likely to contain a
mixture of dyes.
STUDY SHEET
Natural Dyes
Substances with intense colours are often called colorants. Colorants may be natural or
synthetic. Plants are a source of natural colorants.
Colorants used for textile and food are often called dyes.
Colorants used for inks, paints and cosmetics are often called pigments.
Colorants from natural materials may be used with textiles, food, inks, paints and cosmetics.
So the two terms are often used interchangeably.
Strictly speaking, the difference is what happens to their crystal or particle structure during
use: a pigment keeps its structure; a dye loses its structure, e.g. by dissolving in a solvent.
Carotenoids
Carotenes Xanthophylls
Carotenes are found in, for example, carrots, red peppers, oranges and tomatoes. They are
also responsible for the colour of most yellow and orange flowers. Xanthophylls are found in,
for example, nettles, French marigolds, annatto and saffron.
Most carotenes are hydrocarbons though some also contain oxygen atoms. The most
well-known is often simply called carotene (yes, there is a compound called carotene and a
group of compounds called carotenes). It’s found in carrots and has the chemical structure:
H3C
CH3 CH3
H3C CH3
H3C CH3
CH3 CH3
CH3
All carotenoids are based on this carotene structure. The central carbon chain remains the
same, but the groups at either end differ slightly. The central chain consists of 18 carbon
atoms bonded alternatively with single and double covalent bonds with four methyl groups
attached (always in the same positions). The sequence of alternative single and double
covalent bonds is called a conjugated system.
Some carotenoids have molecules containing oxygen atoms. These are xanthophylls. Here
is an example:
O
H3C OH
CH3 CH3
H3C CH3
H3C CH3
CH3 CH3
HO CH3
O
All carotenoids are fat-soluble. They dissolve in organic solvents that are not too polar. They
do not dissolve in water.
Questions
1 Explain why carotene is a hydrocarbon.
2 Write the molecular formula of carotene.
3 Identify the part of the molecule responsible for its colour. Hint: What’s unusual about
the structure of the carotene molecule compared with other hydrocarbons you have
come across?
4 On the chemical structure of carotene given above, highlight the backbone common to
all carotenoids and circle the four methyl groups attached to it.
5 List plant products containing carotenoids that you can obtain easily and not too
expensively.
6 If you want to extract a carotenoid to investigate its potential as a dye, what solvents
might you use and why?
Flavonoids
There are four main types of flavonoids and other less common ones.
Flavonoids
Flavones and flavonols have yellowish colours. The colours are sensitive to pH. The
yellow becomes much deeper in solutions of high pH. The colours of flavones tend not to
fade in strong light as flavonols do, but they are paler.
quercetin, kaempferol and myricetin found in many families, including onions,
horse chestnuts and tea
fisetin found in fustic, nettles etc
morin found in fustic, Osage-orange etc
apigenin found in members of the daisy family
luteolin found in daisy, pea and weld
flavone found in primrose
The yellow colour of onion skins is due to a mixture of flavones and flavonols: quercetin,
kaempferol and quercetin-3-glucoside.
OH
OH
HO O
OH
OH O
quercetin
OH
HO O
OH
OH O
kaempferol
OH
OH
HO O
O
OH O OH
O
HO
CH2 OH
OH
quercetin-3-glucoside
Questions
1 Highlight the 2-phenyl-1,4-benzopyrone backbone in each of the flavonoids found in
onion skins.
2 Highlight the glucoside part of quercetin-3-glucoside.
3 Here is the chemical structure of glucose:
OH OH
HO OH HO OH
or
HO HO
CH2 O OH O OH
representation A representation B
a Explain what representation B tells you about the glucose molecule that
representation A doesn’t.
b Try to explain how quercetin-3-glucoside might be formed from quercetin and
glucose.
4 Why are flavonoids water soluble while carotenoids are not?
5 Why do you think flavonoid colours are sensitive to pH while carotenoids are not?
1
R
Anthocyanidins and anthocyanins are the 2
most highly coloured of the flavonoids. They are R
responsible for the scarlets, reds, violets and
+
blues in many flowers, fruits and vegetables. HO O 3
R
The general structure for an anthocyanidin is
given on the right.
OH
OH
This positive charge on this cation is balanced by an anion, e.g. chloride, Cl-.
The chromophore (functional group responsible for colour) is:
+
O
+
O
OH
Questions
1 Sketch structural formulae for (a) cyanidin, (b) pelargonidin and (c) peonidin. In each
case highlight the chromophore.
2 Now sketch the anthocyanins that would form when glucose reacts with (a) cyanidin, (b)
pelargonidin and (c) peonidin. Hint: Look back at question 3 in the section Flavones and
flavonols.
3 Try finding plants that contain some of anthocyanins listed above. Hint: Think which
names of flowers the anthocyanin’s names remind you of.
4 Outline how anthocyanins might be extracted from plants.
5 What techniques might be used to identify a mixture of anthocyanins?
Anthracenes
There are two major groups: anthraquinones and napthoquinones. They contain several
well-known dyes.
Anthracenes
Anthraquinones Napthoquinones
Some examples:
Anthraquinones alizarin
mungistin madder
purpurin
Napthoquinones juglone walnut
alkanin
hypericin St. John’s wort
Questions
Here is the structure of a napthoquinone called juglone:
O
O OH
1 Why do you think ethyl ethanoate was used for the extraction rather than water?
2 What other solvents might you try?
3 Why is the extraction mixture refluxed?
4 How could you determine the yield of juglone?
5 How could you calculate the possible yield of juglone from 50 kg of walnut rinds?
INFORMATION SHEET
This sheet contains extracts of articles about extracting natural plant dyes and using them to
dye, for example fabrics.
You may do your own research and add to this list.
Please be aware that these articles do not contain heath and safety information. You will
have to do a risk assessment before you carry out any work. Make sure risk assessments are
checked by your teacher before you begin work.
O OH
It can be extracted from the rind of the walnuts (Juglans regia). It represents an important
landmark in the use of natural silk dyeing since ancient times.
Procedure
Cut the rind from six walnuts in small pieces. Place them in a round bottomed flask, add
100 cm3 ethyl ethanoate and fit a condenser.
Set up a hot water bath. The temperature is raised to 70 ºC and the solution is maintained in
reflux (45 minutes). Filter and evaporate the solvent. The brown solid obtained should be
dried and weighed.
There are numerous other dyes available from different parts of plants – roots, bark, stems,
leaves, fresh/dried flowers (fresh fruit juices tend to fade easily). Some plants give better
results than others and it is best to make precise notes of everything you try out. Some plant
dyes, such as powdered madder root are available from plant dye websites.
Divide the blueberry solution into three bowls. Add vinegar to one bowl in small amounts
until the blueberry solution turns pink and add baking soda to a second bowl in small
amounts until the blueberry solution turns dark purple. Students will then have three
separate anthocyanin shades to dye materials over a range of colour. After adding vinegar
and baking soda to blueberry pigment, the dye will be weak.
The quantities that follow will be sufficient to dye 0.5 kg of dry cotton material. This is about
three to four T-shirts. You will need at least two large pans which you do not plan to use for
cooking food and a stove to heat these pans.
Washing. Place the cotton in boiling water, adding washing soap and 2– 3 tablespoons of
washing soda. Boil for an hour and then leave to soak for 24 hours before rinsing the cotton
well.
Mordanting. Mordants prepare the cotton fibres and help them to absorb the dye better. It
is possible to dye without using mordants, but using mordants will generally give much
better, brighter and more permanent colours. Many different chemicals can be used as
mordants, most of which are very poisonous. Before you put the wool or cloth into the dye,
you must soak it in a mordant. The most common mordants are alum, copper sulfate,
potassium dichromate(VI), iron(II) sulfate and tannin. Often two mordants are mixed
together for the best results.
Alum mordant: Add 1 small teacup of alum and, if available, 2 level tablespoons of cream
of tartar to 5 litres of water (quarter of a large water bucket). Dissolve the chemicals in
warm water and leave cotton to soak for 24 hours.
Tannin mordant: Tannin powder can be bought but you can also use bark from trees
known to contain high levels of tannin. Use 2 heaped tablespoons of the powder or 500 g
of bark from African wattle, gum tree (eucalyptus species) or mimosa thorn tree. Bring to
the boil in 5 litres of water and leave cotton to soak for 24 hours.
Copper sulfate mordant: Mix 500 g of gum tree bark with 1 heaped teaspoon of copper
sulfate. Again, bring to boil in 5 litres of water and leave cotton to soak for 24 hours.
Metal mordants: You can make mordants from iron, chrome or tin by boiling some of
these metals with water. To make iron mordant, for example, boil 5 litres of water with 2
cups of vinegar and 1 cup of rusty nails for one hour. Leave it to stand for 24 hours and
then pour off the solution. This solution is the mordant.
Different mordants will give different colours from the same dye. Again, you can experiment
to see what results you get. Alum mordant usually gives the best results as it is cheap, very
reliable and gives bright colours. Salt, vinegar and wood ashes can also be tried as mordants
if nothing else is available.
Plant materials. Collect the flowers, leaves, roots, bark and berries you plan to use. About
500 g of plant material is needed, about enough to fill half a 20 dm3 water bucket. You need
less for wood or bark. Boil the plant matter with 10 dm3 of water (half a full water bucket)
for about one hour until the dye is dark in colour. Then strain out all the plant material. Now
you are ready to dye the cotton.
Dyeing. Rinse off the mordant with clean water. Now add the wet fabric to the hot dye.
Bring the dye to just under boiling temperature and let the mixture simmer, but not actually
boil. Keep the material moving gently to ensure that the dyeing will be even. Keep the
material in the dye for at least half an hour – depending on how strong you want the colour
to be. Take it out and rinse the material several times until the water becomes clear. Give a
final wash with soap, then rinse and dry.
Extracting colours
Adapted from The Viking Deception, Nova, Original broadcast: February 8, 2005;
www.pbs.org/nova/vinland
Follow the recipe below for your berry or onion skin type to make your dye. Take the
following precautions:
wear goggles
use potholders or mitts when touching hot pots
be careful not to spill dyes on your skin or clothing because they stain.
Make a chart on a separate sheet of paper, with areas large enough to record your results.
After you have made the dye, record its colour and intensity (e.g. blue, very light) in your
chart.
Dye recipe
Boil about 500 cm3 of water.
For onions: Add red or yellow onion skin preparations. (For each type of onion skin, place
a large handful of onion skins in knee-high nylon stocking. Make a knot in the stocking at
top.)
For berries: Add 1 cup blueberries or blackberries.
Simmer for 30 minutes.
Cool, then carefully pour dye through sieve into the spouted measuring cup.
For onions: Discard nylon sacks and pour dye into jar. Seal jar.
For berries: One student should hold the cheese cloth over the jar so that the cheese
cloth dips inside while another student slowly pours the dye into the jar. The cheese
cloth will catch berry particles. Discard berries. Seal jar.
Red onion anthocyanin
Yellow onion quercitin
Blueberry anthocyanin
Blackberry anthocyanin
Teacher notes
One assessment requirement for the unit is that students must produce:
a report detailing the extraction of a natural (plant) dye together with details of its
application to three different fabrics including:
identifying your chosen dye and researching a method for its extraction
detailing the type of dye and the method used to make it, the scientific principles
underlying the process together with the apparatus used and any appropriate risk
assessments
with the highest marks gained if they show that (this has been taken from the specifications)
Thorough research has produced comprehensive and workable method of extracting a
natural (plant) that is firmly rooted in science.
Initial plan into a method of extracting a natural (plant) dye was comprehensive with no
error and yielded workable methods. Appropriate modifications to the method of
extraction of the dye are suggested.
The awarding body teacher guidance notes suggest:
Candidates will need to complete the small scale extraction of a natural (plant) dye. Natural
dye extraction could be extraction of lizarin from the common madder plant or indigo from
the indigo plant.
Presumably ‘lizarin’ should be ‘alizarin’. It is difficult to imagine that students will have easy
access to madder plants or woad (‘the indigo plant’).
More likely options are onion skins, nettles, flowers such as marigolds and geraniums,
carrots and fruit such as blackcurrants, blackberries, raspberries, cherries and redcurrants.
Extraction
Students are provided with several examples in Information sheet: Extraction and dyeing
methods. They may be asked to find further information and add this to the examples given.
Students then need to consider variables such as solvents, time, temperature, pre-treatment
of plant material and so on.
Health and Safety
It is important that students carry out detailed risk assessments. You must check these
before they begin practical activities. Some of the health and safety issues in the articles
listed include:
Eye protection should be worn for all practicals
Ethyl ethanoate [HIGHLY FLAMMABLE] [IRRITANT]
Chrome alum [IRRITANT]
Regarding the article ‘Three dye plants – Woad’ it states ‘…with a pinch of’. Students should
realise it is bad practice to handle chemicals with their fingers. For example they might adapt
it to ½ a spatula full.
Dyeing
Again, students can get ideas from Information sheet: Extraction and dyeing methods. One
possibility for streamlining the dyeing tests, however, is to use multifibre strip (see below). It
is relatively inexpensive and will reduce the number of experiments to set up to investigate
dyeing effectiveness.
SDC Multifibre Strip
The SDC Colour Experience (Museum) handles the supply to educational establishments at a
greatly reduced rate. The price is £2/metre plus VAT plus a charge of £1/order to cover
postage and packing.
The SDC multifibre test fabric is made up of 6 different fibres, each is a band of about
15 mm. The fibres are: secondary cellulose acetate (Dicel); bleached unmercerized cotton;
nylon 6.6; polyester (Terylene); acrylic (Courtelle); wool worsted.
SDC Colour Experience, Perkin House, 1 Providence Street, Bradford, BD1 2PW
telephone 01274 390955; fax 01274 392888; www.colour-experience.org
Answers to questions
Carotenoids
1 Explain why carotene is a hydrocarbon.
Answer: Its molecules are made up of carbon and hydrogen atoms only
2 Write molecular formula of carotene.
Answer: C40H56
3 Identify the part of the molecule responsible for its colour. Hint: What’s unusual about
the structure of the carotene molecule compared with other hydrocarbons you have
come across?
Answer: The chain of alternating single and double covalent carbon-carbon bonds
4 On the chemical structure of carotene given above, highlight the backbone common to
all carotenoids and circle the four methyl groups attached to it.
5 List plant products containing carotenoids that you can obtain easily and not too
expensively.
Answer: Examples are listed in the text.
6 If you want to extract a carotenoid to investigate its potential as a dye, what solvents
might you use and why?
Answer: Carotenoids are non-polar molecules and do not dissolve in highly polar solvents
such as water. They dissolve in non-polar organic solvents such as hexane or
cyclohexane.
Flavonoids
1 Highlight the 2-phenyl-1,4-benzopyrone backbone in each of the flavonoids found in
onion skins.
Answer: See black solid ovals on diagrams below
OH
OH OH
HO O HO O
OH OH
OH O OH O
OH
OH
HO O
O
OH O OH
O
HO
CH2 OH
OH
5 How could you calculate the possible yield of juglone from 50 kg of walnut rinds?
Answer: Weigh the walnut rinds and express the yield in terms of grams of juglone per
100 g of walnut rinds. Then scale up to 50 kg.
Dyeing with natural dyes
Most natural dyes are acid dyes, which is why they bond to wool, but not to cotton.
1 Explain the term ‘acid dye’.
Answer: Acid dyes are used mainly for wool and polyamides. They are anionic and
applied in an acid dye bath. The anionic group has a negative charge. This can form
ionic bonds with those parts of the fabric molecules that have a positive charge.
The use of natural dyes is much improved by using a mordant. The fabric is treated with
a solution of metal ions; these form a bridge between the fabric molecules and the dye,
a process called mordanting.
2 Give some examples of mordants that are used with natural dyes.
Answer: The most common mordants are alum, copper sulfate, potassium
dichromate(VI), iron(II) sulfate and tannin. Often, two mordants are mixed together
for the best results.