Chemistry CBSE Practical Project

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Contents

History of DYES

DYE

Some Natural Dyes and their sources


Synthetic dye
Types of Dyes
Chemical Classification

Azo Dye
As Dyes and Pigments
Some Azo Dye Compounds and their structure

REQUIREMENTS

Para Red Dye


Names and Properties
Synthesis
Procedure and Observation

Fluorescent Dye

Resources Required
Procedure
Reactions
Observations

Bibliography

History of
DYES
Dyestuffs are a branch of chemistry inspired
by many people in history. The earliest written
records of use of dyestuffs was found in China
around 2600 B.C. Alexander the Great during his
conquest of India in 327 B.C., mentions about the
beautifully printed cottons that he saw during
one of his expeditions. Around 1745, the dye
INDIGO was grown in England, which was
imported from India.
In
1868, a German chemist produced
ALIZARIN, which was found to be useful as a
synthetic substitute. In 1887, ALIZARIN YELLOW
was used as a mordant dye. And 40 years later,
Baeyer and Sunder had developed INDIGO SOL-O,
which was a versatile dye that found various
applications.

One cannot forget the contribution of Dupont


International in the development of various kinds
of dyes. By 1970s, the Ciba-Geigy introduced
the CIBACRON-F series, which was considered to
be the most recent development of time. Since

then the dyestuffs created a new revolution in the


world of colours.

DYE:
A dye is a colored substance that has an affinity
to the substrate to which it is being applied. The
dye is generally applied in an aqueous solution,
and requires a mordant to improve the fastness
of the dye on the fiber.

Some Natural Dyes and their sources


Colour/Class
Yellow/flavono
id
Red/anthraqui
none
Blue/indigoid

Name
Weld quercetin
safflower

Kermes cochineal
alizarin
Indigo, woad
Tyrian purple

Purple/indigoi
d

Source
seeds, stems, leaves of
Reseda luteola
North American oak bark,
Quercus tinctoria nigra
dried petals of Carthamus
tinctorius
insects, Coccus ilicis
insects, Dactylopius
coccus
madder plant roots, Rubia
tinctorum
indigo plant leaves,
Indigofera tinctoria L.
mollusks, Murex brandaris

Black/chroma
n

Logwood

heartwood,
Haematoxylon
campechianum L.

Synthetic dye
The first human-made (synthetic) organic dye,
mauveine, was discovered serendipitously by
William Henry Perkin in 1856. Many thousands of
synthetic dyes have since been prepared.
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.

Dye types
It distinguishes based on the process of
application to various substrates. They are
subdivided with examples as follows-

ACID DYES: They are salts of sulphonic


acids and can be applied to wool, silk,
polyurethane fibres and nylon.

Example:
Orange.

Orange-1,

Methyl

BASIC DYES: They contain amino groups,


which are acid form water-soluble salts. They
attach themselves to the anionic sites on the
fabrics. They are used as dye in reinforced
nylons and polyesters.
Example:
Malachite green,
Congo red.

DIRECT DYES: They are water-soluble and


are directly applied to fabrics such as cotton,
rayon, wool, silk and nylon that form
hydrogen bonds with water.
Example: Martius yellow, Congo
red.

DISPERSE DYES: These dye in the form of


minute particles of suspension diffuse into
the fabric. They are used for dyeing the
synthetic fibres like polyesters, nylon and
polyacrylonitrile.
Example : Celliton fast pink
B,Celliton fast blue B
FIBRE REACTIVE DYES:

They attach
themselves to the fibre by an irreversible

reaction. Dyeing is fast and colour is


retained for a long time.
Example: 2,4 dichloro-1,3,5-triazine.

INSOLUBLE AZO DYES: They are directly

synthesized on the fibre. The colour is not


fast. They are used for dyeing cellulose,
silk, polyester, nylon, polypropylene,
polyurethane, polyacrylonitrile and leather.
Example: Nitroaniline red.

VAT DYES:

They are water-insoluble and


are reduced to leuco-form before dyeing by
alkaline reducing agent. The fibre is then
exposed to air or to an oxidizing agent
after which the original insoluble dye is
formed in the structure of the fibre.
Example: Indigo, Indigo Sol-O

MORDANT

DYES: They are used


dyeing in the presence of metal ions.
metal ions bind to the fabric and the
acting as a ligand coordinates with

for
The
dye
the

metal ion. The same dye in the presence


of different metal ions gives different
colours.
Example: Alizarin gives rose red with Al 3+,
blue with Ba2+
Food dyes:
One other class that
describes the role of dyes, rather than their
mode of use, is the food dye. Because food
dyes are classed as food additives, they are
manufactured to a higher standard than
some industrial dyes. Food dyes can be
direct, mordant and vat dyes, and their use is
strictly controlled by legislation. Many are
azo dyes, although anthraquinone and
triphenylmethane compounds are used for
colors such as green and blue. Some
naturally-occurring dyes are also used.

Chemical classification
By the nature of their chromophore, dyes are
divided into:

Category:Acridine dyes, derivates of acridine


Category:Anthraquinone dyes, derivates of
anthraquinone

Arylmethane dyes

Category:Diarylmethane dyes, based on


diphenyl methane
Category:Triarylmethane dyes, derivates of
triphenyl methane

Category:Azo dyes, based on -N=N- azo structure

Diazonium dyes, based on diazonium salts

Nitro dyes, based on a -NO2 nitro functional group

Nitroso dyes, based on a -N=O nitroso functional


group

Phthalocyanine dyes, derivatives of phthalocyanine

Quinone-imine dyes, derivativees of quinone


o

Category:Azin dyes

o
o

Category:Eurhodin dyes
Category:Safranin dyes, derivates of
safranin

Indamins
Category:Indophenol dyes, derivates of
indophenol

Category:Oxazin dyes, derivates of oxazin

Oxazone dyes, derivates of oxazone

Category:Thiazin dyes, derivatives of thiazin

Category:Thiazole dyes, derivatives of thiazole

Xanthene dyes, derived from xanthene


o

Fluorene dyes, derivatives of fluorene

Pyronin dyes

Category:Fluorone dyes, based on fluorone

Category:Rhodamine dyes, derivatives of


rhodamine

AZO DYE
Azo compounds are compounds bearing the functional
group R-N=N-R', in which R and R' can be either aryl or
alkyl. IUPAC defines azo compounds as: "Derivatives of
diazene (diimide), HN=NH, wherein both hydrogens are
substituted by hydrocarbyl groups, e.g. PhN=NPh
azobenzene or diphenyldiazene." The more stable
derivatives contain two aryl groups. The N=N group is
called an azo group.

As dyes and pigments


A Yellow Azo Dye

As a consequence of -delocalization, aryl azo compounds have vivid


colors, especially reds, oranges, and yellows. Therefore, they are used as
dyes, and are commonly known as azo dyes, an example of which is
Disperse Orange 1. Some azo compounds, e.g., methyl orange, are used as
acid-base indicators due to the different colors of their acid and salt forms.
Most DVD-R/+R and some CD-R discs use blue azo dye as the recording
layer. The development of azo dyes was an important step in the
development of the chemical industry.
Azo pigments are colorless particles (typically earths or clays), which have
been colored using an azo compound. Azo pigments are important in a

variety of paints including artist's paints. They have excellent coloring


properties, again mainly in the yellow to red range, as well as lightfastness.
The lightfastness depends not only on the properties of the organic azo
compound, but also on the way they have been absorbed on the pigment
carrier. Many azo pigments are non-toxic, although some, such as
dinitroaniline orange, ortho-nitroaniline orange, or pigment orange 1, 2,
and 5 have been found to be mutagenic.

Some Azo Dye Compounds and their structures

REQUIREMENTS
The items listed below are required for the
preparation of various dyes

Beaker

Test tubes

Spatula

Weight box

Burner

Conical flask

Measuring cylinder

Physical/Digital balance

Pair of gloves, lab coat, etc.

Para Red Dye

IUPAC name :- 1-[(E)-(4-Nitrophenyl)diazenyl]-2-naphthol


Other names :- 1-[(4-Nitrophenyl)azo]-2-naphthalenol,
1-((4-nitrophenyl)azo)-2-naphthol, 1-[(p-nitrophenyl)azo]-2naphthalenol, 1-[(p-nitrophenyl)azo]-2-naphthol,
paranitraniline red, Pigment Red 1,
C.I. 12070, Recolite
Para Red B, Carnelio Para Red BS

Identifiers
CAS number

6410-10-2

ChemSpider

13544963

EC number

229-093-8

Properties
Molecular
formula

C16H11N3O3

Appearance

Red solid

Melting point

248 - 252 C

Hazards
R-phrases

R36/37/38

S-phrases

S26, S36

Para Red (paranitraniline red, Pigment Red 1, C.I. 12070) is a


chemical dye. Chemically, the dye is similar to Sudan I. The dye was
discovered in 1880 by von Gallois and Ullrich, and was the first azo
dye. It dyes cellulose fabrics a brilliant red, but is not very fast. The
dye can be washed away easily from cellulose fabrics if not dyed
correctly. Throughout making Para Red, the solution will become
acidic and basic. Small amounts of byproducts may be left over after
the Para Red dye is made that may be acidic or basic, but if made
correctly there are little of these and the byproducts have no effect.

Synthesis
Para Red is prepared by diazotisation of para-nitroaniline at ice-cold
temperatures, followed by coupling with -naphthol.

PREPARATION OF PARA RED DYES

Procedure :NaOH solution is prepared by dissolving 0.4g of NaOH

flakes in 4mL of water.


2g of NaOH and 0.g of -Naphthol were weighed.
The solutions were prepared as follows:
Solution A: 2g of Paranitro aniline,20mL of water and 8mL
of conc.HCl.
Solution B: 2g of NaNO2 and 20mL of water.
Solution C: 0.2g of -Naphthol dissolved in 10%NaOH
solution and was diluted with water (10mL)
All the three solutions are kept in an ice bath for 30 min.
Solution A was added to Solution C and then Solutions B
was added to this solution slowly with constant stirring and
then filtered and dried.
Para Red was obtained

Observation-

The filtrate after drying was deep red in


colour. It gave needle shaped crystals on drying.

FLUORESCENT DYE

Resorcinol

Phthalic Anhydride

Sodium Hydroxide

Concentrated Sulphuric Acid - mL

Procedure : Take 2 g Resorcinol and 2 g of Phthalic anhydride


and add 2 mL of Concentrated Sulphuric acid to it.

Heat the contents on a burner till the contents turn


black.
Cool the contents and add to 20 mL of 5% Sodium
hydroxide in a conical flask.
Vary concentration of Sodium hydroxide and water
to obtain different intensities of colour.

Reactions

Observation of fluorescene :Prepare a solution of fluorescein by dissolving 5


milligrams (or spatula tip size) of the sample in 50
mL 0.1 M NaOH solution. Place the solution in a vial
and place it on a black non-reflective surface, such
as a lab bench. Place a bright light source (sunny
window works well) on the opposite side of the
bench from the observer and note the appearance

of the solution. In this case, the color observed is


primarily due to absorbance of some wavelengths of
visible light passing through the sample from the
light source.
Next observe the same solution at a position 90
degrees from the light source. The color observed
from this perspective is primarily due to
fluorescence.
Finally, in a darkened room shine a long wave UV
lamp at the sample vial. The vials should visibly
glow from the fluoresced light

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