DYES

Compile By

Dr. Amish B. Patel

Asst. Prof. in Chemistry
Faculty of Engineering Technology And
Research.

Introduction
A dye or a dyestuf is usually a
coloured
organic
compound
or
mixture that may be used for
imparting colour to a substrate such
as cloth, paper, plastic or leather.
A
Pigment
particles
remain
clustered together in suspension.
Pigment molecules carry their own
color.

Difference between Pigments

and Dyes
Pigment

Dye

color theory
complex phenomenon that combines
the physics of light
chemistry of colored objects
biology of the eye
behavioral sciencessocial & cultural meaning of color

Colour And Constitution

Colour :
The
psychological
sensation
which
is
produced
when
the
light
of
certain
wavelength reaches the eye is known as the
colour.
The colour is dependent on and varies with
the nature of the light illuminating the
coloured substance.
When white light is incident on a substance,
If white light is reflected completely, the substance will appear
light.
If white light is absorbed completely, the substance will appear
black.
5

When a beam of visible light strikes a coloured

substance, certain wavelengths are absorbed and others
are reflected. Those reflected compose the colour of the
substance.
The substance absorbs wavelength in the blue-green
region of the spectrum, it appears red.
6

Light is made up of bands of

varying wavelengths

Reflection
White can only be
broken up by prisms
or by colorants such
as pigments and
dyes
This surface has no
colorant so the light
is reflected

It can be fully absorbed by the

surface

Or a transparent surface may let all of the light pass

through
or
a colored surface may absorb part of the spectrum

10

Relationship of colour absorbed and complementary

colour observed
Wavelength
Absorbed (nm)

Colour
absorbed

Complementar
y colour

400-435

Violet

Yellow-green

435-480

Blue

Yellow

480-490

Blue-green

orange

490-500

Green-blue

Red

500-560

Green

Purple

560-580

Yellow-green

Violet

580-595

Yellow

Blue

595-605

orange

Green- Blue

605-750

red

Blue-Green

11

Colour And Constitution

The colour of a compound is related to its
chemical constitution.
According to Otto Witts theory (1876), a dye
is made up of two parts, Chromophores and
Auxochromes.

12

Chromophores :
The colour of organic compounds is due to the
presence of certain multiple bonded groups called
chromophores. The compound containing a
chromophoric group were called as chromogens.
( Greek Chroma = colour and phorein = to bear)
Auxochromes :
Certain groups, while not producing colour
themselves,
when
present
along
with
chromophores in an organic subsatance, intensify
the colour, such colour assisting groups are called
Auxochromes.
( Greek Auxanein = to increase and Chroma =
colour)
13

The auxochromes serve two functions,

They increase the intensity of the

colour, e.g.
(i) Benzene ( No Chromophores ) is colourless.
(ii) Nitrobenzene ( -NO2 as a Chromophores ) is pale Yellow
colour.
(iii) p-Nitroaniline (-NO2 as a Chromophores and -NH2 as a
Auxochrome ) is dark Yellow.

They make the chromogen a dye by fixing

it to the fabric or the material to be dye
either by association or by salt formation.
The fixing of the dye to the fiber is due to
the formation of chemical bond between the
fiber and auxochrome.
14

Some Typical Chromophores

15

Some Typical Auxochromes

16

Nomenclature of Dyes
1. Commercial Naming of Dyes:
The trademark name of the class comes first and
is followed by words, letters or numbers. These
describe the shade and other characteristics,
strength, physical form etc.
e.g. Y or G = Yellow ( German word gelb = yellow)
R = Red (German word rot = red)
B = Blue
O = Orange
e.g. Vat Pink R, R indicates the red tone of the
pink.
17

Sometimes the letters are used to

represent the class of dye. e.g. Alizarin Blue
D, the letter D indicates that dye is a direct
cotton colour.
2.Colour Index Naming of Dyes:
The best method for the nomenclature of
dyes is Colour Index, a publication
sponsored by the, society of Dyers &
colourists
(England)
and
American
Association of Textile Chemists & colourists.
In this, each dye is given two reference
18
numbers, one relating to its class with

Basic Textile Definitions

Fibers = A smallest unit of textile materials.
Usually classified by flexibility, fineness,
and a ratio between length and diameter
(L/D ratio)
Natural Fibers = Fibers that come from
animals (wool, silk etc.), plants (cotton, jute
etc.) or mineral material (asbestos).
Synthetic Fibers = Man-made fibers or
artificial fibers which is usually comes from
chemical agents.
19

Yarns = Yarn is a long continuous

length of interlocked fibers.The
combinations of fibers using some
twisting (Z and S twists) in order to
make strong and stable yarns.
Fabrics = The products of weaving,
knitting or non-woven processes.
Normally, fabrics have a certain
thickness and can withstand tear
and tensile forces.

20

Structure of Cotton
( Bioglucose unit in cotton)

The side groups of these units are primary and

secondary alcoholic hydroxy groups which make the
fibre hydrophilic. This property of cotton fibre is
responsible for its dyeing.
21

Structure of Wool

Wool is the natural animal fibre. It is composed of

protein substance.
It is dyed with either acidic or basic dyes through
the formation of salt linkage with amino or carboxylic
acid end groupings.
It may also be dyed with reactive dyes that form
covalent bonds with available amino groups.
22

Structure of Silk

Silk is also the natural animal fibre and also a

protein fibre. It is linearly arranged polypeptide
structures called fibroin.
Whensilk hydrolysed, the main aminoacids isolated
are glycine, alanine, serine and tyrosine.
23

Classification of Dyes
Dyes are classified in various ways according
to,
( 1 )
The method of application to the
fiber,
( 2 ) Their chemical constitution,
( 3 ) The types of material to be dyed, and
( 4 )
The intermediates from which they
are
prepared.
24

Dyestufs can be classified by many methods as

follows:
1. by their ionic (e.g. cationic, anionic and non-ionic)
2. by their fiber dyeabilities (e.g. on cellulosic, protein,
polyester, polyamide etc.)
3. by their names (e.g. acid, direct, disperse, reactive, basic
etc.)
4. by their chemical structures (e.g. azo, anthraquinone,
stilbene etc.)
5. by their origins (e.g. natural, synthetic)

25

Classification of dyes according to

applications.

1. Acid dyes :

. These dyes are usually the sodium salts of the colour

acids, which may contain sulphonic acid or phenolic
group.
. Which are used to dye fibers having basic groups,
such as wool, silk and polyamides.
. Application is generally made under acidic condition,
which cause protonation of the basic groups.
Dye- + H+ + Fiber Dye- H+ - Fiber
. This is a reversible process and it can be removed by
washing.
. Examples: Picric acid, Orange II, Naphthol Yellow.

26

Structure of Orange II

27

2. Basic dyes :
Which have a basic amino group.
Which is protonated under the acidic conditions
of the fibers.
It gives intense and brilliant shades.
They are used for dyeing silk and wool directly.
For dyeing cotton it needs a mordant like tannic
acid.
Examples: Crystal violet, Methylene Blue.

28

Structure of Crystal Violet

29

3. Direct dyes :
These are a class of dyes that become strongly
adsorbed on cellulose.
Direct dyes are large, flat and linear molecules.
A direct dye contains acidic or basic auxochrome
with the opposite polar group present in the
chemical structure of the fiber.
it is used for dyeing wool, silk and cotton.
Fiber-NH2 + HO-DYE Fibre-NH3+ - O- - DYE
Generally common salt is used to promote dyeing
because i.p.o. salt it favors establishment of
equilibrium with a minimum of dye remaining in
the dye bath.
Examples: Congo Red.
30

Structure of Congo Red

31

4. Vat dyes :
Vat dyes are insoluble but their reduced forms
are soluble.
Reduced forms of vat dye are obtained by
treating the dye compound with some reducing
agent such as alkaline sodium hyposulphite.
The cloth to be dyed is immersed in the vat.
After the reduced dye has been adsorbed on the
fiber, the original insoluble dye is reformed by
oxidation with air or chemicals.
Vat dyes are quite expensive and used on cotton
fabrics.
Examples: Indigo, Anthraquinone
32

Structure of Indigo

33

5. Disperse dyes :
Disperse dye molecules are small and have
some hydroxyl or amino groups.
Disperse dyes are insoluble in water but can be
dispersed in a colloidal form in water.
The fine dye particles are absorbed into the
crystal structure of the fabric.
It is used for dyeing of cellulose acetate, nylon,
polyester and polyacrylonitrile fibers.

34

Classification of dyes according to

their Chemical Constitution
No
.

Class

Subcl
ass

Nitro

---

Examples

Picric acid
Yellow S
2

Nitroso

Naphthol

---

Fast Green O
35

No
.

Class

Subcl
ass

Azo

Monoazo

Examples

Methyl Orange
Bisazo

Congo Red
Trisazo

Direct Black EW
Polyazo

----

36

No
.

Class

Subcl
ass

Azo

Mordant
azo

Examples

Eriochrome Black T
Stilbene
azo

Chrysophenine O
Pyrazolo
ne azo

Tartrazine

37

No
.

Class

Subcl
ass

Diphenyl
Methane

----

Examples

Auramine O
5

Triphenyl
Methane

----

Malachite Green
6

Xanthene

----

Fluorescein

38

No
.

Class

Subcl
ass

Indigoid

----

Examples

Indigo
8

Thiazole

----

Basic Yellow T
9

Thiazine

----

Methylene Blue

39

No
.

Class

Subcl
ass

10

Cyanine

Methine

Examples

Astrafloxine FF
11

Anthraquinono
id

----

Perion Fast Green BR

12

Hydroxy
Ketone

----

Alizarin Dark Green W

40

Azo Dyes
If one azo group Monoazo dyes
two azo group Diazo dyes
Three azo group Trisazo dyes
Four azo group Tetrokisazo dyes
Five azo group Polyazo dyes
The diazotisation process was discovered by Petter
Greess in 1862, according to him, Azo dyes are
prepared by two process:
1) Diazotising primary aromatic amine by treatment
of Nitrous acid (HNO2) in aqueous medium at 05C to form diazonium salts.
2) Coupling the above diazonium salt with phenols
& aromatic amines etc. to give a azo compound.
41

Application of Azo Dyes

they are applicable to,
All the natural & synthetic fiber
Paper, leather, rubber and other material
Pure form of certain dye are used for
colouring foodstuf.
Used as Indicator, drugs, stain in
bacteriological analysis.
Combination of azodyes & metallic salt are
valuable in the paints, varnishes, lacquers
and allied industries.
42

Acid Dyes
Used mainly on wool, silk, and nylon
They have acid chemical groups in their dye
molecules
Reaction involves acid, salt, heat, agitation and time
Amount of acid and rate at which it is added afects
the rate at which the dye bonds
Salt slows the bonding process, helping the dye
color the fiber evenly. It attaches to the dye first.
Heat afects the leveling of the dye bath by speeding
up the
chemical reaction
Generally the dye bonds slowly until 160 F
Agitation helps keep both chemicals and heat evenly
distributed
43

VAT DYES
INDIGO, probably the oldest
dye known to man, is one of
the most important members
of this group.
Natural indigo extracted from
the plant 'Indigofera tinctorie'
was used by the Egyptians in
200 BC.
The first synthetic indigo was
introduced to the textile trade
in 1897 & had the efect of
completely replacing the
natural product.
44

Synthesis of Methyl Orange

( 1 ) Diazonium salt of
sulphanilic acid
(It2 is
) N,N-Dimethyl
Aniline for acid-base titrations
a valuable indicator
because it gives yellow colour in basic solution and
red color in acid solution. The change in colour is due
to the change in the structure of the ion.
45

Synthesis of Congo Red

( 1 ) Tetrazotised
benzidine
direct dye and acid
used for dyeing cotton. Also used
( It2 is) Naphthionic

as indicator, being red in alkali and blue in acid

solution.
46

Synthesis of Bismark
Brown

( 1 ) Tetrazotised mdiaminobenzene
(It 2is) used
m-diaminobenzene
in boot polishes and for dyeing wool and
cotton.
47

Synthesis of Malachite
Green

Greek world Leuco = Colourless

It has a deep green blue colour. It is used as a direct
dye for wool and silk.
48

Synthesis of Alizarin

It forms ruby red crystals which dissolve in alkali to

give purple solutions. It used to dye wool and cotton.
49

Synthesis of Indigo Dyes

It contain carbonyl chromophore. It is a dark-blue

crystalline compound, insoluble in water. It is used for
dyeing cotton.
50

Synthesis of Eriochrome
Black-T

It is used as an indicator in EDTA

titration.

51

Synthesis of Fluorescein

It is red powder and it is insoluble in H 2 O.

When it is dissolved in alkalies, it gives a reddishbrown solution which on dilution gives a strong
yellowish-green fl uorescence.
Its sodium salt is known as Uranine and used to dye
wool & silk.
52

Synthesis of Naphthol
Yellow-S

It is used as the sodium or potassium salt.

It is cheap dye for wool and silk in an acid bath, giving
pure yellow shade.
It is non poisonous & is used as food colour.
53

Dyeing Process
Dyeing Processes can be applied in many
stages such as
1.Mass-coloration of the molten fibers
2.Fiber Dyeing
3.Yarn Dyeing
4.Fabric Dyeing
5.Garment Dyeing
54

1. Mass-coloration of the molten fibers

This method is for dyeing the molten fibers or
plastic chips or textile polymers with pigment
dyes. After that, the molten polymers will
extrude from a spinneret to form fibers.
Disadvantage: very difficult to clean.
2. Fiber Dyeing is the method of dyeing fibers
before blending with other colors to give
fancy yarns or fabrics.
Note: This is used for special purposes only.
3. Yarn Dyeing is the method of dyeing yarns
in forms of packages dyeing.
55

4. Fabric Dyeing is the method after weaving,

knitting, or non-woven to make fabrics. This
is very popular method of dyeing as the dyed
fabrics will be processed further to garment
industries very easily.
Dyeing forms of the fabric dyeing can be
used in 2 ways:
1. Open width form using the fabrics to
spread without any creases and dye them.
2. Rope form using the fabrics with the form
like a rope (many creases and look like a
rope)
56

It is a known fact that the main material for

fabric construction is yarn. Knitting is the second
most frequently used method, after weaving, that
turns yarns or threads into fabrics.
Weaving is the most basic process in which two
diferent sets of yarns or threads are interlaced with
each other to form a fabric or cloth. One of these
sets is called warp which is the lengthwise yarn
running from the back to the front of the loom. The
other set of crosswise yarns are the filling which are
called the weft or the woof.
A knitted fabric may be made with a single yarn
which is formed into interlocking loops with the help
of hooked needles.
57

Some people classify into:

1. Exhaustion Process
This method is using lot of water as shown
in Liquor Ratio (ratio between water and
goods) This should immerge the goods
into dye solution for a long time in order to
let the dye penetrate into the goods. This
will lead to produce more waste water than
the continuous process.
Advantage: inexpensive, no need to train
the worker to look after and run them
properly.
Disadvantage: lots of water needed, very
slow process (60-120 min/batch.)
58

2. Continuous Process
This method is designed by putting
diferent machinery into a sequence so
that it can produce the dyed fabric in one
pass.
Advantage: very fast process (10-100
m/min), small amount of water in the
process.
Disadvantage: very expensive, need to
train the worker to look after and run
59
them properly.

5. Garment Dyeing
This method is the last process of the
dyeing of goods.
However, the
penetration of the dye solution may not
be completely passed to the fibers such
as between the buttons, zippers etc.
Normally, it is used for socks & sweater
dyeing etc.

60

Name of Dyestufs

Fibers that can be

dyed
Acid

Silk, wool, polyamide, leather

Basic

Acrylic

Direct

Cellulosic, viscose

Disperse

Acetate, triacetate,

polyamide,
Reactive
Vat
Sulphur

polyester, acrylic
Cellulosic, viscose, protein

Cellulosic
Cellulosic

61

Dyeing method
Direct Dyeing
When a dye is applied directly to the fabric
without the aid of an affixing agent, it is called
direct dyeing. In this method the dyestuf is
either fermented (for natural dye) or chemically
reduced ( for synthetic vat and sulfur dyes)
before being applied. The direct dyes, which are
largely used for dyeing cotton, are water soluble
and can be applied directly to the fiber from an
aqueous solution. Most other classes of synthetic
62
dye, other than vat and sulfur dyes, are also

Yarn Dyeing
When dyeing is done after the fiber has been
spun into yarn, it is called Yarn dyeing.
There are many forms of yarn dyeingPackage Dyeing,
Space Dyeing.

Package
Dyeing

63

Fastness Properties
These are the properties of the dye
which indicate the tolerance of the dyes
on the fibers towards the action of
various

foreign

agencies

like,

light,

washing, heat (sublimation), rubbing,

perspiration, milling (rotating in wash
wheel).
64

1. Color fastness: These measures the resistance of

the textiles when they are exposed to various
agencies. A scale of 1 - 5 is employed.
where, 1 denotes poor fastness while 5 denotes for
excellent.

2. Light fastness: These measures the resistance of

dyed fabric to light under standard conditions. A
scale of 1 - 8 is employed.
where, 1 denotes poor light fastness while 5 for best
fastness to light.

3.

sublimation fastness: A dyed piece is kept 65

in