CERTIFICATE

This is to certify that “Shwetank Pratap Tiwari” student of class

12th A ,”Delhi Public School, Varanasi” has prepared this project in
Accordance with guidance issued by “All India Senior Secondary
Board”(AISSCE) and “Central Board Of Secondary Education”
(CBSE)
I hereby certify that this project prepared by the above mentioned
student under the supervision of

Mrs. Anju Singh Ms. Nilanjana Chakorverty

(HOD Chemistry) (PGT Chemistry)

Mr. Praval Singh Chouhan

(PGT Chemistry)

Examiner’s signature
 ACKNOWLEDGEMENT
I Shwetank Pratap Tiwari studying in the 12th grade , am
extremely grateful to few proficient people, without the help
of whom this project report would have been impossible to
create.
My sincere thanks to my friends, teacher and parents.
I am also grateful of my reputed school
DELHI PUBLIC SCHOOL, VARANASI
for giving me the opportunity to present the completion of
our hard work.
 INTRODUCTION
DYE
A dye is a colour substance that has an affinity to the substrate to which
it is being applied. The dye is generally applied in an aqueous solution,
and may require a mordant to improve the fastness of the dye on the
fiber.
Dyes are colored because they absorb only some wavelengths of
visible light. Dyes are usually soluble in water whereas. Some dyes can
be rendered insoluble with the addition of salt to produce a lake pigment.
Evolution of Dyes
The preparation and application of dyestuffs is one of the oldest forms of
human activities. Evidences of which were found by Excavation at
archaeological sites where ancient fabrics were unearthed. There is also
mention of it in the Bible and other works of classical antiquity. It was in
2600 BC when earliest written records of the use of dyestuffs were
found in China.

Perhaps one of the real breakthroughs in the history of dyes came in

1856 when a teenager who was experimenting at his makeshift
laboratory in home made a certain discovery that acted as a sort of
launching pad for the modern chemicals
industry.

William Perkin an 18-year-old student was

working on chemical synthesis of natural
products. In a classic case of serendipity, the
young William Perkin chanced upon his now
famous 'Aniline Mauve' dye while he was
attempting to synthesize quinine, the only cure
for malaria. Perkin named his colour Mauveine, after the French name
of non-fast colour which was made of natural dyes. So "Mauve" (a
basic dye) was the first synthetic dye stuff. Mauve was a derivative of
coal tar. It was the first mass-produced dye, that was commercially
available and the idea was born that a colour could be made in the
factory. It was indeed a revolution.
 What makes the Dyes coloured ?
This is a very common question that occurs in everybody's mind. The
answer to which is explained by the presence of a substance
called Chromophore in the dyes. By definition dyes are basically
aromatic compounds. Their structures have aryl rings that has
delocalised electron systems. These structures are said to be responsible
for the absorption of electromagnetic radiation that has varying
wavelengths, based upon the energy of the electron clouds.
It is actually because of this reason that chromophores do not make dyes
coloured. Rather it makes the dyes proficient in their ability to absorb
radiation. Chromophores acts by making energy changes in the
delocalised electron cloud of the dye. This alteration invariably results in
the compound absorbing radiation within the visible range of colours
and not outside it. Human eyes detects this absorption, and responds to
the colours.

Another possibility is that if the electrons are removed from the electron
cloud, it may result in loss of colour. Removing electrons may cause the
rest of the electrons to revert to the local orbits. A very good example is
the Schiff's reagent. As sulphurous acid reacts with pararosanilin, what
happens is that a sulphonic group attaches itself to the compound's
central carbon atom. This hampers the conjugated double bond system
of the quinoid ring, and causes the electrons to become localised. As a
consequence the ring ceases to be a chromophore. As a result,
the///dye///becomes///colourless.
To conclude chromophores are the atomic configurations which has
delocalised electrons. Generally they are represented as carbon, nitrogen,
oxygen and sulphur. They can have alternate single and double bonds.
TYPES OF DYES
Natural-Dye:
Natural dyes are simply dye substances extracted from natural sources.
Although the main source of dyes for early times, 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 haematoxylin,
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-Dye:
Dyes derived from organic or inorganic compound are
known as synthetic dyes. Examples of this class of dyes are
Direct, Acid, Basic, Reactive, Mordant, Metal complex, Vat,
Sulphure , Disperse dye etc. Synthetic dyes quickly replaced
the traditional natural dyes.

They cost less, they offered a vast range of new colors, and
they imparted better properties to the dyed materials dyes
are now classified according to how they are used in the
dyeing process.
Acid dye:

Acid dyes are water-soluble anionic dyes, containing one or

more sulfonic acid substituents or other acidic groups. An
example of the class is Acid Yellow 36.

Acid yello36
Acid dyes are water-soluble anionic dyes that are applied to
fibers such as silk, wool, nylon and modified acrylic fibers using
neutral to acid dye baths. Acid dyes are not substantive to
cellulosic fibers. Most synthetic food colors fall in this category.
The dyeing process is reversible and may be described as
follows:
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 recently they have been successfully used with some
readymade fibers, especially the acrylics. Basic dyes were
originally used to color 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
colors with exceptional fastness to acrylic fibers. They can be
used on basic dyeable variants of nylon and polyester.

Basic Brown 1 is an example of a cationic dye that is readily

protonated under the pH 2 to 5 conditions of dyeing.

Basic Brown 1
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 colors 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.

Direct orange 26 is a typical direct dye.

Direct orange 26
Azoic Dye:
Azoic 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 color. Unless they
are carefully applied and well washed, they have poor fastness
to rubbing or crocking.

The production of bluish red azoic dye from the following two
components is an example.
Nitro Dye:
Nitro dyes are polynitro derivatives of phenols containing at
least one nitro group ortho or para to the hydroxyl group . It is
used to dye wool. It Consist of two or more aromatic rings
(benzene, naphthalene).

Example:

Maritus yellow

Sulfur 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 colors is that they make the fabric tender, or weaken
its structure, so that it breaks easily. Sulfur dyes are applied to cotton
from an alkaline reducing bath with sodium sulfide as the reducing
agent. They are low cost and have good fastness to light, washings and
acids.
Example:
Disperse Dye:
Disperse dyes were originally developed for
dyeing secondary cellulose acetate fibers. 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 fibers. This
dye class is used to dye polyester, nylon, acetate
and triacetate fibers.

Disperse yellow 3, Disperse Red 4, and Disperse

Blue 27 are good examples of disperse dyes.

Example:
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.

An example of a vat dye is Vat Blue 4 (Indanthrene).

Vat Blue 4
Mordant Dye:
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 colored complexes (lakes). These materials are
usually used for the dyeing of cotton, wool or other
protein fiber. The metallic precipitate is formed in the
fiber producing very fast colors highly resistant to both
light and washing.

Example:
Reactive Dye:
These dyes react with the cellulosic fiber to form a
covalent bond. This produces dyed fiber 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.

Example: This type is the Reactive Blue 5 dye shown

below,

Reactive Blue 5
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 coloring
synthetics, plastics, gasoline, oils and waxes.

Example:

Solvent yellow32
Properties of dyes:

 These dyes are economical dyes and are generally used

to produce dark shades such as dark greens , dark blues
and blacks.

 These dyes have good leveling and color fastness

properties.

 The interaction between fiber and dye is established

through very strong ionic bonds , which are formed
between the anionic groups of the colorant and
ammonium cations on the fiber. Chromium or the
metal ion acts as bridge between the dye and fiber ,
which gives rise to a very strong linkage , resulting into
excellent fastness properties.
Some dye application:

Name of Dyes Application

Man made fiber(Nylon),

Acid dye Natural fiber (Silk, Wool)

Man made fiber (Viscose),

Direct Dye Natural fiber (Cotton)

Man made fiber (Viscose),

Vat dye Natural fiber (Cotton, Silk, Wool)

Nylon, Polyester, Acrylic, Tri-acetate, Di-

Disperse dye acetate

Basic dye Jute, Acrylic

Reactive dye Cotton, Wool, Silk, Viscose, Nylon

Sulfur dye Cotton, Viscose

Mordant dye Cotton, Wool, Silk

Pigment Cotton, Man made fiber

Mineral Cotton, Wool, Silk

Azoic dye Cotton, Viscose

Aniline Black Cotton

Rapid and Rapidson

dye Cotton

Onium dye Cotton, Jute

Hazards of using synthetic dyes.
Synthetic Dyes find use in a wide range of industries but are of primary
importance to textile manufacturing. Wastewater from the textile
industry can contain a variety of polluting substances including dyes.
The environmental and subsequent health effects of dyes released in
textile industry wastewater are becoming subject to scientific scrutiny.
Environmental legislations are being imposed to control the release of
dyes, in particular azo-based compounds, into the environment.
Wastewater from the textile industry is a complex mixture of many
polluting substances ranging from organochlorine-based pesticides to
heavy metals associated with dyes and the dyeing process. During textile
processing, inefficiencies in dyeing result in large amounts of the
dyestuff being directly lost to the wastewater; which ultimately finds its
way into the environment.

Colorants that enter the wastewater streams normally pass through a

wastewater treatment plant where they are eliminated to a large degree
by adsorption on sludge. The extent to which residual amounts reach the
surface waters depends on the efficiency of treatment processes. Low
concentrations of dyes in waste water do not normally pose any
significant environmental hazard. Environmental problems arise mainly
from inefficient removal of dyes or disposing the untreated dye effluent
to water receiving bodies. This is normally the case in most developing
countries.
Advantages of Natural Dyes
 Minimal Environmental Impact – Because they come
from natural sources, natural dyes are not harmful to the
environment, which makes it so appealing for consumers.
Natural dyes are biodegradable and disposing them don’t
cause pollution.
 Renewable – Natural dyes are obtained from renewable
sources that can be harnessed without imposing harm to the
environment.
 Color pay-off – If you’re going for a soft hue or soothing
shade, natural dyes can help you achieve that look.
 Safe – Some natural dyes, such as carmine found in
lipsticks, will not cause harm or health problems when
ingested.
Disadvantages of Natural Dyes
 Cost – A larger amount of natural dyes may be needed in order to
dye a specific amount of fabric as opposed to synthetic dyes. For
instance, one pound of cotton may be dyed with just five grams of
synthetic dye, whereas 230 grams of natural dye are needed to dye
the same amount of material. Since that is the case, using natural
dyes is more expensive than synthetic dyes.
 Color pay-off – Color pay-off from natural dyes tend to fade
quickly. More so, quality may not be as consistent than what
synthetic dyes can deliver.
 Availability – Another issue with natural dyes is their availability.
It can be difficult to produce because the availability of raw
materials can vary from season to season, place, and species,
whereas synthetic dyes can be produced in laboratories all year
round.
 Harmful Effects – Natural dyes can also be harmful to some
extent. Logwood has ingredients, hematein and hematoxylin, that
can be have harmful effects when inhaled, ingested, or absorbed
through the skin. Bloodroot, another natural dye source, can cause
irritation and inflammation when inhaled. More so, natural dyes
may need mordants for application. While these substances help
the dye stick to fabrics, they can also be toxic. Example of
mordants used in natural dyes are aluminum, copper, iron, and
chrome.
 Sustainability – While natural dye sources are renewable,
sustainability can still be an issue for natural dyes because
producing them require vast areas of land.
Prepare 2-Naphthol Aniline

or

Phenyl-azo-β-Naphthol dye

AIM: Preparation of 2-Naphthol Aniline

Theory
2-Naphthol aniline dye or Phenyl-azo-β-naphthol is an orange-
red dye. It belongs to a large class of azo-compounds, all of
which contain the characteristic grouping

Azo compounds are all coloured compounds. For the

preparation of this dye, aniline is diazotised and then diazonium
salt thus obtained is subjected to coupling reaction with 2-
naphthol.
Apparatus

 One 100 mL conical flask

 One 100 mL beaker
 One 250 mL beaker
 Ice-bath
 Glass-rod
 Buchner funnel
 Water pump

Chemicals Required

 Aniline = 4.5 ml
 Sodium nitrite = 4g
 2-Naphthol = 7 g
 Cone, hydrochloric acid = 10 ml
 Glacial acetic acid = 40 ml
Procedure

1. Take a 100 ml conical flask and add 2.25 ml of aniline, 5 ml

of conc. HCl and 10 ml of water. Cool this solution to 5°C
by placing the conical flask in a trough containing ice- cold
water.

2. In a 10 ml beaker dissolve 2 g of sodium nitrite in 10 ml of

water and cool this solution also to 5°C.

3. Now slowly add sodium nitrite solution to the solution of

aniline in conc. HCl.

4. Dissolve 3.5 g of 2-naphthol in 30 ml of 10% NaOH

solution taken in a 250 ml beaker and cool this solution to
5°C by placing in an ice bath. Some crushed ice may be
added directly to fecilitate cooling.

5. Now add the diazotised solution very slowly to the naphthol

solution with constant stirring. The mixed solutions
immediately develop a red colour and the phenyl-azo-β-
naphthol rapidly separates as orange-red crystals.

6. When the addition of diazo solution is complete, allow the

mixture to stand in ice-salt mixture for 30 minutes, with
occasional stirring. Filter the solution through a buchner
funnel under suction from the pump. Wash the phenyl-azo-
β-naphthol with water and dry the crystals obtained by
pressing between the folds of filter paper.
 7. Recrystallise the product from glacial acetic acid. Filter the
crystals obtained at the pump. Wash with a few ml of
ethanol to remove acetic acid. Phenyl-azo-β-naphthol is
obtained as orange-red crystals. Expected yield is 1.5 g and
melting point is 133°C.

Result

Weight of phenyl-azo-β-naphthol obtained as orange-red

crystals =…….g.

Melting point of phenyl-azo-β-naphthol is …….°C.

Precautions

1. The solution of the aniline hydrochloride should be cooled

to 5°C, and this temperature should be maintained
throughout the addition of the sodium nitrite solution.

2. Addition of sodium nitrite should be very slow because the

reaction is exothermic and may cause the temperature to
rise.