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CHEMISTRY
INVESTIGATORY PROJECT -
DYES
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MAHINDRA WORLD SCHOOL
Chemistry Project
Exam: AISSCE
Name:
Reg. No:
Year: 2021-2022
Class: XI
Date:
Subject: Chemistry
Code:
Chemistry Investigatory Project
Submitted to:
The Central Board of Secondary Education
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In partial fulfilment of the required for Grade XI
in Chemistry (2020-2021)
by
Student name:
Roll No:
under the supervision and guidance of
Ms. Chitra Srinivasan
Department of Chemistry
Mahindra World School
CE
RTI
FIC
AT
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Certified that this is a bonafide project work done by
Ms. , Reg. No. of class XI, Mahindra
World School, Natham Post office, Chengalpattu –
603004, during the academic year 2021-2022.
Date:
Place:
Internal Examiner External Examiner Principal
ACKNOWLEDGEMENT
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I, of class XI, would like to express my
greatest gratitude to our Principal, Ms. Suganthi
Medasani, and the people who have helped and
supported me throughout my project.
It is my humble pleasure to acknowledge my deep
gratitude to my Chemistry faculty Ms. Chitra
Srinivasan, for all the support, monitoring and
constant encouragement, without her guidance this
project would not have come forth. Special thanks
to Mr. Ashok who helped me with my project
throughout the year.
I wish to thank my parents for their undivided
support and interest who inspired and encouraged
me to go my own way without which I would be
unable to complete my project. A special thanks to
all my friends who appreciated me for my work
and motivated me.
Last but not least, I would like to thank the
almighty for giving me strength, focus and
constant determination in the successful
completion of my project.
IND
Sr. No EX
Topic Page no
1. Aim 1
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2. Introduction 2
3. History of Dyes 3-6
4. Dye Structure and Colour 7-8
5. Dye Synthesis 9-11
6. Types of Dyes 12-16
7. Uses Of Dyes 17-19
8. Dyes vs Pigments 20
9. Drawbacks of Dyes 21-23
10. References 23
AIM OF THE PROJECT
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To explore more about dyes, their
history, structure, synthesis, types,
and uses.
INTRODUCTION
A dye is a coloured compound, normally used in
solution, which is capable of being fixed to a
fabric.
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The dye must be ‘fast’ or chemically stable so that
the colour won’t get washed away with soap and
water, fade on exposure to sunlight, etc.
Dyeing is normally done in a special solution,
containing dyes and particular chemical material.
After dyeing, dye molecules make an uncut
chemical bond with fibre molecules. The
temperature and time taken are 2 key factors in
dyeing.
The dyes can be obtained from animals, vegetables,
or even from minerals with no or very little
processing required.
By far, the greatest source of the dyes has been the
plants- notably roots, berries, bark, leaves, wood,
etc. but only a few of them have been used on a
commercial scale.
HISTORY OF DYES
Natural dyes
The development of natural dyes took place at the same time
after the technique of weaving had been discovered in about
5000 BC. In India, the use of natural dyes for dyeing, painting
and printing goes to the prehistoric periods. Ajanta paintings,
dated as far back as the 1st century AD, were painted with
natural dyes. These paintings are evidence of the use of
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colourful garments worn by men and women of that era.
Natural dyes can be categorized under vegetative or animal
origin. Until the latter half of the nineteenth century, all dyes
with the exception of a few mineral colours were of animal or
vegetable origin. Colouring matter was extracted from the
roots, stems, leaves, flowers, barks and fruits of plants and
from certain insects and shellfish by an elaborate series of
extraction processes.
The earliest written record of the use of natural dyes was
found in China dated 2600 BC. A Chemical test of red fabrics
found in the tomb of King Tutankhamen in Egypt showed the
presence of alizarin, a pigment extracted from madder. Tyrian
purple, a well renowned natural dye, occupied a prominent
position in Roman history (Schetkly, Ethel jane Mc. D.,
1986). Indigo has been used in the textile industry for the last
several thousand years. It is one of the earliest dyestuffs
recorded in history and still retains its supreme importance
even today.
A Greek artefact known as the Stockholm Papyrus details
dyestuffs and techniques in almost a recipe fashion as it was
practised in Egypt in the third and fourth centuries CE. The
great detail in which the preparation of the fibres and the
dyeing materials and the dyeing process itself are recorded
has led scholars to believe that it had to have been practised
for
thousands of years previously in order to raise the process to
such science and art.
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Synthetic dyes
The influence of William Henry Perkin
Although the first synthetic dye – picric acid, which produced
a bright yellow on silk – was invented in 1771, the man
widely regarded as responsible for the rise of synthetic dyes
was William Henry Perkin. In 1856, while still a chemistry
student, Perkin, who was trying to synthesize the anti-malarial
drug quinine from coal tar, accidentally discovered the first
major aniline or coal-tar derived dye. A black residue that
formed during his experiments, when dissolved in methylated
spirit was found to produce a purple solution that worked well
on silk. The colour of the dye, which came to be known as
‘mauve’ or ‘Mauveine’, was a fashion sensation.
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William Perkin
Structure of mauve
The development of synthetic dyes post-mauveine
In the next few years following the discovery of Mauveine,
research activity towards the development of other synthetic
dyes intensified especially in Britain, Germany, and France.
For the most part, chemists concentrated on aniline as the
starting material, and this resulted within a very short time
period in the discovery of several other synthetic textile dyes
with commercial potential. In fact, the term ‘aniline dyes’
became for many decades synonymous with synthetic dyes.
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The most successful product which immediately followed
Mauveine was Fuschine, a rich red dye, also to become
known as Magenta, which was introduced in 1859.
Subsequently, and very rapidly, a range of new dyes,
providing a wide range of bright fashion colours emerged -
yellows, reds, blues, violets and greens, as well as browns and
blacks. These dyes proved to be superior not only in colour to
natural dyes, but they were also found to be easier to apply
and more economic.
Fuschine
DYE-STRUCTURE AND COLOUR
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Advances in structural theory led to investigations of
correlations between chemical constitution and colour. In
1868 German chemists Carl Graebe and Carl
Liebermann recognized that dyes contain sequences of
conjugated double bonds: X=C―C=C―C=C―…,
where X is carbon, oxygen, or nitrogen.
In 1876 German chemist Otto Witt proposed that dyes
contained conjugated systems of benzene rings bearing
simple unsaturated groups (e.g., ―NO2, ―N=N―,
―C=O), which he called chromophores, and polar
groups (e.g., ―NH 2, ―OH), which he
named auxochromes. These ideas remain valid, although
they have been broadened by better recognition of the
role of specific structural features.
He had also claimed that auxochromes impart dyeing
properties to these compounds, but it later became clear
that colour and dyeing properties are not directly related.
Witt suggested the term chromogen for specific
chromophore-auxochrome combinations.
The colours of dyes and pigments are due to the
absorption of visible light by the compounds.
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The electromagnetic spectrum spans a wavelength of
range from long radio waves (about 10 km [6.2 miles]) to
short X-rays (about 1 nm [1 nm = 10–9 metre]), but
human eyes detect radiation over only the small visible
range of 400–700 nm. Organic compounds absorb
electromagnetic energy, but only those with several
conjugated double bonds appear coloured by the
absorption of visible light. Without substituents,
chromophores do not absorb visible light, but the
auxochromes shift the absorption of these chromogens
into the visible region. In effect, the auxochromes extend
the conjugated system. Absorption spectra are used to
characterize specific compounds.
In visible spectra, the absorption patterns tend to form
broad bands with maxima at longer wavelengths
corresponding to more extended conjugation. The
position and shape of the absorption band affect the
appearance of the observed colour. Many compounds
absorb in the ultraviolet region, with some absorptions
extending into the violet (400–430 nm) region.
Thus, these compounds appear yellowish to the eye—
i.e., the perceived colour is complementary to the
absorbed colour. Progressive absorption into the visible
region gives orange (430–480 nm), red (480–550 nm),
violet (550–600 nm), and blue (600–700 nm);
absorption at 400–450 and 580–700 nm gives green.
Black objects absorb all visible light; white objects
reflect all visible light. The brilliance of colour increases
with decreasing bandwidth. Synthetic dyes tend to give
brilliant colours. This undoubtedly led to their rapid rise
in popularity because, by comparison, natural dyes give
rather drab, diffused colourations.
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DYE SYNTHESIS
Dyes are synthesized in a reactor, filtered, dried, and
blended with other additives to produce the final
product.
The synthesis step involves reactions such as
Sulfonation: It is the process of attaching the sulfonic
acid group (–SO3H) directly to the carbon atom in an
organic compound.
Halogenation: A type of chemical reaction where
hydrogen atoms are replaced by halogen atoms in a
molecule.
Amination: The process by which an amine group is
introduced into an organic molecule.
Diazotization: The chemical process where a primary
aromatic amine is converted into the corresponding
diazonium salt of the amine.
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Coupling: The series of organic reactions that involve
the joining of two chemical species usually with the help
of a metal catalyst.
followed by separation processes that may include
distillation, precipitation, and crystallization.
In general, organic compounds (like naphthalene) are
reacted with an acid or an alkali along with an
intermediate (such as a nitrating or a sulfonating
compound) and a solvent to form a dye mixture. The
dye is then separated from the mixture and purified.
On completion of the manufacture of the actual colour,
finishing operations, including drying, grinding, and
standardization, are performed. These are important
for maintaining consistent quality.
Let us now look at an example to have a clear
understanding of the synthesis of dyes:
Azo Dyes:
Azo dyes are organic bearing the functional group R−N=N−R′
( R and R′ are usually aryls). They are a commercially
important family of azo compounds, i.e., compounds
containing the linkage C-N=N-C. Azo dyes are widely used to
treat textiles, leather articles, and some foods.
Preparation:
Most azo dyes are prepared by azo coupling, which
entails an electrophilic substitution reaction of an aryl
diazonium cation with another compound, the coupling
partner. Classically coupling partners are other aromatic
compounds with electron-donating groups:
ArN2+ + Ar′H → ArN=NAr′+ H+
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In practice, the acetoacetic amide is widely used as a
coupling partner:
ArN2+ + Ar′NHC(O)CH2C(O)Me →
ArN=NCH(C(O)Me)(C(O)NHAr′) + H+
Azo dyes are also prepared by the condensation of
nitroaromatics with anilines followed by reduction of
the resulting azoxy intermediate:
ArNO2 + Ar′NH2 → ArN(O)=NAr′ + H2O
ArN(O)=NAr′ + C6H12O6 → ArN=NAr′ + C6H10O6 +
H2O
For textile dying, a typical nitro coupling partner used
would be disodium 4,4′-dinitrostilbene-2,2′-
disulfonate.
Since anilines are prepared from nitro compounds, some
of the azo dyes are produced by partial reduction of
aromatic nitro compounds. Many azo dyes are
produced by reactions from pre-existing azo compounds
as well. Typical reactions include metal complexation
and acylation.
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TYPES OF DYES
Dyes are compounds that possess the ability to stick to the
fabric. While the quality of dyes varies with the manufacturer,
the dyes which take less time to colour the fabric and are
chemically stable are most preferable. Dying the fabric forms
strong chemical bonds between dye molecules and the fabric.
Temperature and time are two important factors that
determine the durability of the dye.
There are different types of dyes that are present in the market
and they can be classified on the following basis:
Based on Source:
1. Natural Dye
Dying has been a flourishing trade since long, in
different parts of the world. The dyes used in times
before progress in chemical science were only natural.
Dyes were derived from plants and animals. Indigo trade
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and farming in northern India are an example of the scale
of trade.
Synthetic dyes have taken over the industry because of
less cost and more reliability but natural dyes such as
hematoxylin, carmine and orcein are still in use in the
industry.
2. Synthetic Dye
All the dyes that are derived from organic and inorganic
chemical compounds are synthetic dyes. Acidic dyes,
basic dyes, azoic dyes, nitro dyes, vat dyes, mordant
dyes, and sulphur dyes, etc. are synthetic dyes.
Based on application:
3. Direct Dye
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These dyes are applied to the fabric by preparing an
aqueous solution and submerging the fabric in it. Fabrics
that can form hydrogen bonds with the dye molecule are
dyed with direct dyes.
These became popular because the use of mordants or
other binders became obsolete with this coming into use
for cotton dyeing.
Direct dyes provide better fastness than other dyes but
lack colour brilliance in comparison to other dyes. This is
compensated by diazotization treatment. Fabrics such as
cotton, linen, rayon, wool, silk and nylon are dyed with
direct dyes.
These are also azo dyes and are used to dye the fabrics
directly by placing them in an aqueous solution of the
dye.
4. Disperse Dye
These dyes are relatively insoluble in water and were
formed to dye secondary cellular acetate fibres.
Disperse dyes are prepared by grinding of dye into fine
particles and are dissolved in the solution with dispersing
agents.
Fiber absorbs the colour upon submerging into the
solution. Polyester, nylon, acetate and triacetate fibres
are dyed using disperse dyes.
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These dyes are applied in the form of a dispersion of
minute particles of the dye in soap solution in the
presence of phenol or benzoic acid.
3. Reactive Dye
Reactive dyes are cationic dyes, which are used for
dyeing cellulose, protein and polyamide fibres.
Reactive dyes are found in powder, liquid and print paste
form.
In reactive dyes, covalent bonds are formed with
cellulose fibres.
Such bonds give high fastness. It happens because strong
bonds formed at the molecular level are hard to break.
Hence, they show better comparative durability against
light and washing.
5. Solvent Dye
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These dyes are soluble in alcohol, chlorinated
hydrocarbons and liquid ammonia but not water. These
dyes show extensive use in the petroleum industry.
The colours of the dye is rendered by dissolving into the
target which is generally lipids or non-polar solvents.
These are used to colour plastics, synthetics, gasoline, oil
andcxes.
5.Acid Dyes
These are azo dyes and are characterized by the presence of
acidic groups.
6. Basic Dyes
The dyes contain organic basic groups such as NH2 or NR2.
7. Vat Dyes
These dyes are water-insoluble and before dyeing these are
reduced to colourless compounds in wooden vats by alkaline
reducing agents.
All the types of dyes are in demand in the market due to the
growing industries in developing countries. Future market
trends are favourable for India being a developing country.
The recent trade skirmishes between US and China has given
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India a chance to grow its domestic market by serving the
clients of the Asia Pacific region. Therefore, dyes
manufacturers of India are expecting market growth.
USES OF DYES
General Uses
Dyes are widely used by industries for inks and tinting.
Dyes are used by textile industries for cloth colouring.
Since they’re free of heavy metals, they’re also used in
cosmetic preparation.
Edible dyes are often used in food and confectionery.
Sulphur dyes are used for effective textile printing.
Medical Uses
Due to the use of dyes as biological stains, dye therapy was
the initial basis for chemotherapy and many modern drugs
have dye antecedents. Dyes used in the medical field today
may certainly be found as drug colourants, in vital staining,
tracing and histopathology, but some also remain as
chemotherapeutics. The discovery of the aniline dyes in the
19th century and contemporary investigation of their use as
biological stains by scientists such as Koch and Ehrlich led to
the idea of selectivity and formed the basis of modern
chemotherapy; several of these dyes remain in
pharmacopoeias.
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While the development of therapeutics has tended to avoid
coloured compounds due to unwanted colouration, the modern
application of photosensitizing dyes, both in the fields of
cancer therapy and anti-infection, depends on this
phenomenon. In addition, the fluorescence of some anticancer
photosensitizers allows their use as tumour localizing agents,
which is particularly useful in precancerous conditions.
It is also fitting that dyes employed in Ehrlich's original
studies, such as the phenothiazinium dye, methylene blue, are
now in clinical use for disinfecting donated blood products.
More modern applications include photosensitisers in light-
activated therapies for cancer and infection and biocidal dyes
for use in medical textiles. Such areas have also contributed to
an increasing knowledge base concerning dye toxicity and
mutagenicity.
Use In Laboratories
Indicators are the chemical dyes that change colour
depending on the hydrogen ion or hydroxide ion concentration
in the solution.
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Indicators help in identifying whether the given solution is
acidic, basic or neutral in nature. These may be natural or
synthetic.
Dyes are frequently used in biological labs for the staining of
cells and tissues (microbiology). Staining enhances
visualization of the cell and certain cellular components under
a microscope and highlights the metabolic processes
happening in them. This gives us a clear picture of their
anatomy. Commonly used dyes for staining are
fuchsin, crystal violet, malachite green, methylene blue,
safranin, eosin, etc.
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Different stains under microscope
DYES VS PIGMENTS
Dyes and pigments are both considered as
‘colourants’ but are very different from each other:
Category of Dyes Pigments
difference
Size Very small Comparatively
larger
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Stability Vulnerable to Resistant against
fading fading
Bonding Functional groups Functional groups
bind easily don’t bind;
between the dye requires a binding
and the substrate agent
Combustion Combustible Relatively lesser
properties combustible
Chemical Typically organic Mostly inorganic
properties
Longetivity Shorter Longer
Solubility Soluble Insoluble
DRAWBACKS OF DYES
Harmful Effects
Dyes absorb and reflect sunlight and water. This
diminishes photosynthetic activity of algae and seriously
influences the food chain.
Many dyes and their breakdown products are
carcinogenic, mutagenic and toxic to life.
Textile dyes can cause allergies such as contact
dermatitis and respiratory diseases.
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The highly toxic and mutagenic dyes decrease light
penetration and photosynthetic activity, causing oxygen
deficiency and limiting downstream beneficial uses such
as recreation, irrigation and drinking water.
Azo dyes when ingested can cause serious DNA damage.
Environmental Pollution
Air pollution
Most processes performed in textile mills produce
atmospheric emissions. Gaseous emissions have
been identified as the second greatest pollution
problem for the textile industry.
Air pollution is the most difficult type of pollution to
sample, test and quantify in an adult.
Water Pollution
The wastewater from the textile plant is classified as the
most polluting of all the industrial sectors, considering
the volume generated as well as the effluent composition.
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Dyes can remain in the environment for an extended
period of time, because of high thermal and photo
stability to resist bio degradation.
The increased demand from textile products and the
proportional increase in their production, and the use of
synthetic dyes have together contributed to dye
wastewater becoming one of the substantial sources of
severe pollution problems in current times.
Remedial Measures
Enhance the effluent disposal treatment plants through
Reverse Osmosis (RO) and the resultant water can be
used as fresh water for the region.
Industries can switch over to Cleaner Production
Technologies(CPT) by using a combination of soft slow
machines, low salt dyes and membranes filtration. This
effectively reduces water consumption by 50%.
Use of activated carbon in the absorption of chemicals in
waste from the dyeing process, which has been shown to
greatly reduce some of the pollutants in the waste.
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REFERENCES
https://www.ifc.org
https://en.wikipedia.org
https://www.britannica.com
https://www.scribd.com
