I.S.C.

Chemistry
Project

Types Of Dyes

Name : Aarav Vidhawan

Roll No. : B455/2012
Class : XII Section : S1
I.S.C Batch No. : 2021-22
Acknowledgement
I would like to thank my Chemistry teacher, Mr. S.K.Sur, for
giving me such an interesting topic to work on for my Chemistry
Project. I would also like to think him for all the new things I
learnt while writing this project.
 Index
SL No. Contents Page No.

1. Introduction 1
2. History Of Dye 2-3
3. Principles of Colour 4-5

4. Major Differences Between Dyes and 6-8

Pigments

5. Types Of Dyes 9-10

6. Synthetic Dyes: 11-17

(a) Acid Dye 11
(b) Basic or Cationic Dye 11-12
(c) Direct Dye 12
(d) Azoic Dye 13
(e) Nitro Dye 13-14
(f) Disperse Dye 14
(g) Vat Dye 14
(h) Mordant Dye 15-16
(i)Reactive Dye 16
(j) Solvent Dye 16
(k) Sulphur Dye 17
Introduction 1

A dye is a coloured compound, normally used in solution, which

is capable of being fixed to a fabric. The dye must be ‘fast‘ or
chemically stable so that the colour will not wash 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 have an uncut Chemical bond with fibre
molecules. The temperature and time controlling are two key
factors in dyeing. The dyes were obtained from animal, vegetable, or
mineral origin with no or very little processing. By far the greatest
source of dyes has been from the plant kingdom, notably roots,
berries, bark, leaves, and wood, but only a few have ever been used
on a commercial scale.
History Of Dye 2

Textile dyeing dates back to the Neolithic period. Throughout

history, people have dyed their textiles using common, locally
available materials. Scarce dyestuffs that produced brilliant and
permanent colours such as the natural invertebrate dyes Tyrian
purple and crimson kermes were highly prized luxury items in the
ancient and medieval world. Plant-based dyes such as woad, indigo,
saffron, and madder were important trade goods in the economies
of Asia and Europe. Across Asia and Africa, patterned fabrics were
produced using resist dyeing techniques to control the absorption of
colour in piece-dyed cloth. Dyes from the New World such as
cochineal and logwood were brought to Europe by the Spanish
treasure fleets, and the dyestuffs of Europe were carried by
colonists to America.

Dyed flax fibres have been found in the Republic of Georgia in a

prehistoric cave dated to 36,000 BP. Archaeological evidence shows
that, particularly in India and Phoenicia, dyeing has been widely
carried out for over 5,000 years. Early dyes were obtained
from animal, vegetable, or mineral sources, with no to very little
processing. By far the greatest source of dyes has been from
the plant kingdom, notably roots, berries, bark, leaves, and wood,
only a few of which are used on a commercial scale.

Ancient hieroglyphs describe the extraction and application of

natural dyes. Countless attempts have been made to extract dyes
 3

from brightly coloured plants and flowers, yet only a dozen or so

natural dyes found widespread use. Undoubtedly most attempts
failed because most natural dyes are not highly stable and occur as
components of complex mixtures, the successful separation of which
would be unlikely by the crude methods employed in ancient times.
Nevertheless, studies of these dyes in the 1800s provided a base for
the development of synthetic dyes, which dominated the market by
1900.

The first synthetic dye, mauve, was discovered serendipitously

by William Henry Perkin in 1856. The discovery of mauveine started
a surge in synthetic dyes and in organic chemistry in general.
Other aniline dyes followed, such as fuchsine, safranine, and induline.
Many thousands of synthetic dyes have since been prepared. The
discovery of mauve also led to developments within immunology and
chemotherapy. In 1891 Paul Ehrlich discovered that certain cells
or organisms took up certain dyes selectively. He then reasoned
that a sufficiently large dose could be injected to kill pathogenic
microorganisms if the dye did not affect other cells. Ehrlich went on
to use a compound to target syphilis, the first time a chemical was
used in order to selectively kill bacteria in the body, he also used
methylene blue to target the plasmodium responsible for malaria.
 4
Principles Of Colour
Dyes possess colour because they :-

1. Absorb light in the visible Spectrum (400 – 700 nm)

2. Have at least one chromophore (colour-bearing group)

3. Have a conjugated system i.e. a structure with alternating

double and single bonds.

4. Exhibit resonance of electrons, which is a stabilizing force in

organic compounds.

When any one of these features is lacking from the molecular

structure the colour is lost. In addition to chromophores, most
dyes also contain groups known as auxochromes (colour
helpers), examples of which are carboxylic acid, sulfonic acid,
amino, and hydroxyl groups. While these are not responsible for
colour, their presence can shift the colour of a colorant and they
are most often used to influence dye solubility.

Regarding the requirement of a chromophore generating colour

in organic compounds, it is important to note that the chromophore
must be part of a conjugated system. Placement of an azo group
between methyl groups produces a colourless compound, while a
yellow-orange colour is obtained when the azo group is placed between
 5

aromatic rings.

Having an extended conjugated system causes a significant

bathochromic shift, i.e. to a darker colour. In addition to
influencing solubility, auxochromes are essential ring substituents in
providing target colours.

Effects of substituent groups within an azo-dye system :-

1. Adding groups of increasing electron-donating ability to the

azobenzene structure has a bathochromic effect.
.
2. Electron-donating (NH2) and electron-accepting (NO2)
groups placed in conjugation provide a bathochromic effect. In this
regard, nitro groups are especially beneficial, contributing to their
prevalence in disperse dye structures.
.
3. Increasing the number of electron-attracting groups conjugated
with the electron-donor has a bathochromic effect.
.
4. The electron-donating effects of amino group are enhanced by
adding alkyl groups to the N-atom.
The Major Differences 6

Between Dyes And

Pigments.

Dyes Pigments
Solubility Soluble in many liquids. Insoluble in water and
most of the solvents.

Number Available in large Comparatively lesser

number. in number.

Light Lower dyes are very Traditionally pigments

fastness much vulnerable. Lights have been found to be
destroy coloured more light fast than dyes.
objects by breaking open
electronic bonding within
the molecule.

Product Traditionally pigments Very high.

Resistance have been found to be
more light fast than
dyes.
 7

Size Dye molecules are Pigment particles are

comparatively smaller; about 1-2 microns in size.
it‘s like comparing a It means that the
football (pigment) to particles can be seen
say a head of a pin under a magnifying glass.
(dye).

Bonding Dye molecules have Pigment requires the help

electrostatic charges if a binder for gluing. As
that serve as a method it is an inert substance
for attaching the dye to which is merely suspended
the concrete. in a carrier/binder.

Imparting Dyes can impart colour by Pigments impart colors by

Colours selective absorption of either scattering of light
the dyes. or by selective absorption

Combustible Combustible. Non-Combustible.

Properties
 8

Chemical Organic Compounds. Normally inorganic

Composition compounds, often
involving heavy toxic
metals.

Longevity Do not last as long as Last longer than dyes.

pigments.
Types Of Dyes 9

Natural dyes are simply dyed substances extracted from

natural sources. Although the main source of dyes for early time,
they have largely been replaced by synthetic dyes, which are usually
more reliable, cheaper and can be supplied more readily. Natural
dyes still in use include hematoxylin, carmine, orcein.

Colouring materials have been used for many thousands of

years by man. Leather, cloth, food, pottery and housing have all been
modified in this way. Some of our most common dyes are still
derived from natural sources. These are termed natural dyes. The
Colour Index uses this as a classification and naming system.

Each dye is named according to the pattern :

Natural + base colour + number

Natural dyes are often negatively charged. Positively charged

natural dyes do exist but are not common. In other words, the
coloured part of the molecule is usually the anion. Although the
molecular charge is often shown on a specific atom in structural
formulae, it is the whole molecule that is charged. Many, but by no
means all, natural dyes require the use of a mordant.

Synthetic Dyes are Dyes derived from an organic or inorganic

compound are known as synthetic dyes. Examples of this class of dyes
are Direct, Acid, Basic, Reactive, Mordant, etc.
 10

Synthetic Dyes quickly replaced natural dyes because They cost

less, they offered a vast range of new colours, and they imparted
better properties to the dyed materials.

Dyes are now classified according to how they are used in the
dyeing process.
 Acid Yellow 36

Acid Dye Preparation process

Basic Brown 1
Synthetic Dyes 11

Acid Dye :
Acid dyes are anionic, soluble in water and are essentially
applied from acidic bath. These dyes possess acidic groups, such as
SO3H and COOH and are applied on wool, silk and nylon when ionic
bond is established between protonated –NH2 group of fibre and
acid group of dye. Overall wash fastness is poor
although lightfastness is quite good. As dye and fibre contain
opposite electrical nature, strike rate and uptake of acid dye on
these fibres is faster; electrolyte at higher concentration is added
to retard dye uptake and to form levelled shades. Acid generates
cation on fibre and temperature helps to substitute negative part
of acid with anionic dye molecules.

An acid dye is a dye that is typically applied to a textile at low

pH. They are mainly used to dye wool, not cotton fabrics. Some acid
dyes are used as food colorants, and some can also be used to stain
organelles in the medical field.

Basic or Cationic Dye :

This group was the first of the synthetic dyes to be taken out of
coal-tar derivatives. As textile dyes, they have been largely
replaced by later developments. They are still used in discharge
printing, and for preparing leather, paper, wood, and straw. More
Direct orange 26
 12

recently they have been successfully used with some readymade

fibres, especially the acrylics. Basic dyes were originally used to
colour wool, silk, linen, hemp, etc., without the use of a mordant, or
using agent. With a mordant like tannic acid, they were used on
cotton and rayon. Basic dyes give brilliant colours with exceptional
fastness to acrylic fibres. They can be used on basic dyeable variants
of nylon and polyester.

Direct Dye :
These are the dyes which can be applied directly to the fabrics
from an aqueous solution. These are most useful for fabrics which
can form hydrogen bonds with the Dyeing of Fabrics. The direct dyes
mainly the basic dyes and were widely hailed because they made it
unnecessary to use a mordant or binder in dyeing cotton. The
colours are not as brilliant as those in the basic dyes but they have
better fastness to light and washing, and such fastness can be
measurably improved by after treatments (diazotized and
developed.)
Direct dyes can be used on cotton, linen, rayon, wool, silk and
nylon. These dyes usually have azo linkage –N=N- and high
molecular weight. They are water soluble because of sulfonic acid
groups.
 Azoic Dye

Maritus Yellow
-Nitro Dye
 13

Azoic Dye :
Azoic dyeing is a technique in which an insoluble Azo dye is produced
directly onto or within the fibre. This is achieved by treating a fibre
with both diazoic and coupling components. With suitable adjustment
of dyebath conditions the two components react to produce the
required insoluble azo dye. This technique of dyeing is unique, in that
the final colour is controlled by the choice of the diazoic and
coupling components. This method of dyeing cotton is declining in
importance due to the toxic nature of the chemicals used.

Azo dyes contain at least one azo group (-N=N-) attached

to one or often two aromatic rings. These dyes are used primarily
for bright red shades in dyeing and printing since most other classes
of fast dyes are lacking in good red dyes. Azoic dyes, called
Naphthols in the industry, are actually manufactured in the fabric
by applying one half of the dye. The other half is then put on and they
combine to form the finished colour. Unless they are carefully
applied and well washed, they have poor fastness to rubbing or
crocking.

Nitro Dye :
Nitro dyes are polynitro derivatives of phenols containing at
least one nitro group ortho or para to the hydroxyl group. It is
Disperse Dye
 14

used to dye wool. It Consist of two or more aromatic rings (benzene,

naphthalene).

Disperse Dye :
Disperse dyes were originally developed for dyeing secondary
cellulose acetate fibres. These dyes are relatively insoluble in
water and are prepared for dyeing by being ground into relatively
fine powder in the presence of dispersing agents. In the dye bath, a
suspension of the dye particle dispersion produces a very dilute
solution of the dyes, which are then absorbed by the fibres. This dye
class is used to dye polyester, nylon, acetate and triacetate fibres.

Vat Dye :
The vat dyes are insoluble complex polycyclic molecules based
on the quinone structure (ketoforms). The term vat comes
from the old indigo method dyeing in a vat: indigo had to be reduced
to light form. Vat dyes are made from indigo, anthraquinone and
carbazole. They are successfully used on cotton, linen, rayon, wool,
silk, and sometimes nylon. Vat dyes are also used in the continuous
piece of dyeing process sometimes called the pigment application
process. The dyeings produced in this way have high wash and light
fastness.
 15

Mordant Dye :
A mordant or dye fixative is a substance used to set (i.e.
bind) dyes on fabrics by forming a coordination complex with the
dye, which then attaches to the fabric (or tissue). It may be used
for dyeing fabrics or for intensifying stains in cell or tissue
preparations. Although mordants are still used, especially by small
batch dyers, it has been largely displaced in industry by directs.

These Dyeing of Fabrics do not dye the fabric directly but

require a binding agent known as mordant. The mordant acts as a
binding agent between the fibre and the dye. Some dyes combine with
metal salts (mordanting) to form insoluble coloured complexes
(lakes). These materials are usually used for the dyeing of
cotton, wool or other protein fibre. The metallic precipitate is
formed in the fibre producing very fast colours highly resistant to
both light and washing.

The term mordant comes from the Latin mordere, "to bite". In
the past, it was thought that a mordant helped the dye bite onto the
fibre so that it would hold fast during washing. A mordant is often
a polyvalent metal ion, often chromium(III). The resulting
coordination complex of dye and ion is colloidal and can be either
acidic or alkaline.
Solvent yellow 32
 16

Mordants include tannic acid, alum, chrome alum, sodium

chloride, and certain salts of aluminium, copper, chromium, iron,
iodine, potassium, sodium, tungsten, and tin.

Reactive Dye :
These dyes react with the cellulosic fibre to form a covalent
bond. This produces dyed fibre with extremely high wash fastness
properties. These are the dyeing of fabrics which contain a reactive
group which combines directly with the hydroxyl or the amino group
of the fibre. Because of the chemical reaction the colour is fast and
has a very long life. Cotton, wool or silk can be dyed with this type
of dyeing of Fabrics.

Solvent Dye :
These dyes are water-insoluble but soluble in alcohols, chlorinated
hydrocarbons, or liquid ammonia. These colours are applied by
dissolving in the target, which is invariably a lipid or non-polar
solvent. The Colour Index uses this as a classification and naming
system. Each dye is named according to the pattern: – solvent + base
colour + number They are used for colouring synthetics, plastics,
gasoline, oils and waxes.
Sulphur Red 7
 17

Sulphur Dye :
The sulphur dyes provide very deep shades, which have excellent
resistance to washing but poor resistance to sunlight. They will dye
cotton, linen, and rayon, but not brightly. A problem with sulphur
dyes especially the black colours is that they make the fabric tender,
or weaken its structure, so that it breaks easily. Sulphur dyes are
applied to cotton from an alkaline reducing bath with sodium
sulphide as the reducing agent. They are low cost and have good
fastness to light, washings and acids.