Basic Requirement For Dyes:: Department of Chemistry A.M.U., Aligarh

Unit III Synthetic Dyes Dr.
Abad Ali 1
Department of Chemistry
A.M.U., Aligarh
B.Sc. (HONS.) VI Semester (C.B.C.S)
Organic Chemistry – AE (CHB 672)
DYES
Dyes are organic colored compounds imparting the color to substrates like hair,
drugs, paints, paper, wax etc.
These are colored because absorbs visible light at certain wavelength.
All colored compounds are not dyes but dyes are colored.
Basic Requirement for Dyes:

 Dyes are usually soluble in water.
 Ability to impart the color.
 Ability to standing with washing, drying, cleaning or exposure to light.
 They should be chemically stable.
 Dyes should be absorbed and retained to material to be dyed.
Classification of Dyes:
Dyes are classified into two types.
1. Natural Dyes
2. Synthetic dyes
1. Natural Dyes
Dyes are obtained from plants like leaves, root, bark etc. and animals are called
Natural Dyes.
For example: Alizarine (obtained from Madder plant), Blue dye (Indigo), Red dye or
Carmine red (Carmic acid) obtained from coccus cacti, cochineal (obtained from
Insect).
Natural dyes are few in numbers and have limited shades/colors.
1. Synthetic Dyes (artificially man made dyes)

The synthetic dyes prepared in the laboratory have huge numbers/Shades. The
starting material for synthetic dyes can be obtained from coal tar distillation.
These are classified based on:
A. Their mode of application on the fibres
B. Chemical structure of the dyes (i.e. presence of the different types of
chromophore)
(A) Mode of application on fibres:

This classification is based on the various methods of dyeing different fibres with dyes.
According to this, dyes can be classified into following types:
I. Direct or substantive dyes
II. Vat dyes
III. Mordant dyes (or indirect or adjective dyes)
IV. Azo dyes (or ingrain or developed dyes)
V. Disperse dyes
VI. Sulfur dyes
Unit III Synthetic Dyes Dr. Abad Ali 2
I. Direct or substantive dyes (soluble in water)

These dyes applied directly to the fabrics in aqueous solution. It consists of
soaking the fabric in an aqueous solution of the dye, taking it out, removing excess of
the solution and then drying. Direct dyes are strongly polar dyes used to dye polar
fabrics (e.g., wool) or moderately polar fabrics (e.g., cotton, rayon). The dyeing of the
fibres is carried out in the presence of common salt, so these dyes are also called salt
dyes such as Congo red.
These dyes are further subdivided into two groups:
(a) acidic dyes
(b) basic dyes
(a) Acidic dyes:

Nitronaphthols (e.g., martius yellow, picric acid, Naphthol yellow-S), acid orange-7
(orange-II) are acidic dyes. These dye, wool and silk (proteinous in nature) directly
due to interaction of the polar acidic group of the dye with the basic (–NH2) group of
the fibre.
For example, orange-II is prepared as follows:
(a) Basic dyes:

These are the cationic dyes containing basic groups such as –NH2, –NHR, –NR2 and
their salts (mostly in the form of HCl and ZnCl2 salts). These are used for dyeing
animal fibres directly but cotton (vegetable fibres) after moderating with tannin.
For example, Malachite green, Magenta, para-rosaniline, etc.
In recent years, azo dyes with –NH2 group, like aniline yellow and butter yellow
are also considered as basic dyes due to their basic nature.
II. Vat dyes (insoluble in water)

“Vat means vessel”
These dyes applied directly on the fibre. These can be used only on cotton &
rayon and not on silk & wool. The dyeing, in this case, is a continuous process and is
carried out in a large vessel called vat. For this reason, these dyes are termed as vat
dyes.
For example, Indigo blue, Tyrian purple (6,6’-dibromoindigo).
These dyes are insoluble in water and first of all converted into water soluble form
(leuco compound) by reduction (referred to as vatting) in alkaline medium which may
be colorless. It is in this form they are introduced into the fabric. The fabric is then dried
in air where oxidation takes place and colored fabric is obtained.
III. Mordant dyes (or indirect or adjective dyes) (insoluble in water)

These dyes are insoluble in water and a third substance is used as a binding
material of the fibre with dye. This third substance is called mordant and such dyes
are called mordant dyes.
In the dyeing process, fibre is dipped in mordant, dried and then again dipped
into the dye solution. Mordant forms a complex with the dye and is deposited on the
fibre giving it a permanent shade.
For acid dyes, a basic mordant [like metal salts Fe(OH)3, Al(OH)3] is used and
for basic dyes, an acid mordant such as tannic acid is used. Alizarin is an example
of mordant dyes. It gives different colors when used with different materials. It gives a
red color with Al and Sn salts, brownish red tones with Cr mordant, and black-violets
with Fe mordant.
Note:
The process of mordant dyeing consists in impregnating the fabric with the
mordant in the presence of mild alkali and a wetting agent followed by the soaking of
the mordanted fabric into the dye bath.
The mordant fixes first to the basic or acidic groups of the fabric and then
combines with the acidic or basic dyes. This imparts superior fastness to light and
washing. With alizarin and the mordant Al(OH)3, the binding of the dye to the fabric is
believed to involve salt formation at the 1–OH group and coordinates at the adjacent
carbonyl group. In other words, a chelate is formed. This chelated structure is
responsible for the excellent light-fastness of most mordant dyes.
IV. Azo dyes (or ingrain or developed dyes) (insoluble in water)

These are applied directly on the fibre. The process includes the diazotization
and the coupling reaction at low temperature on the fibre itself. The fabric is soaked in
an alkaline solution of phenol followed by drying and then immersed in a cold solution
of a diazonium salt. The azo dye is developed directly on the fibre itself. Such dyes,
known as developed dyes, are called Ice colors also because such dyes formed at
low temperature within the fabric.
Para-red is an example of such developed dye.
These dyes may be developed in a reverse order also. The fabric is impregnated with
an amine which is then diazotized and developed by immersion in an alkaline solution
of phenol. The name “ingrain dye” is also given to such dyes. These dyes are
particularly useful in making printed fabrics.
V. Disperse dyes (insoluble in water)

These dyes are insoluble in water, but are capable of dissolving certain synthetic
fibres. Disperse dyes are usually applied in the form of a dispersion of finely divided
dye in a soap solution in the presence of some solubilizing agent such as phenol,
cresol, or benzoic acid etc. The absorption into the fibre is carried out at high
temperatures and pressures. Disperse dyes are used to dye acetate rayons, Dacron,
Nylon and other synthetic fibres.
For example: Celliton Fast Pink B (1-amino-4-hydroxyanthraquinone) and Celliton
Fast Blue B (1,4-N,N’-dimethylaminoanthraquinone).
VI. Sulfur dyes (insoluble in water)

These dyes are soluble in sodium sulfide (Na2S) solution and thus the dyeing
process is carried out in Na2S solution. These dyes are generally used for dyeing
cotton fibre.
(B) Chemical structure of dyes:

The classification of dyes on the basis of chemical constitution (structure):
1. Nitro dyes
2. Nitroso dyes
3. Azo dyes
4. Diphenylmethane dye
5. Triphenylmethane dye
6. Diphenylamine dye
7. Xanthene dye
8. Heterocyclic dye
9. Anthraquinone dye
10. Indigo dye
11. Phthalocyanine dye
12. Florescent dye

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Unit III Synthetic Dyes Dr.

Basic Requirement for Dyes:

1. Synthetic Dyes (artificially man made dyes)

(A) Mode of application on fibres:

I. Direct or substantive dyes (soluble in water)

(a) Acidic dyes:

(a) Basic dyes:

II. Vat dyes (insoluble in water)

III. Mordant dyes (or indirect or adjective dyes) (insoluble in water)

IV. Azo dyes (or ingrain or developed dyes) (insoluble in water)

V. Disperse dyes (insoluble in water)

VI. Sulfur dyes (insoluble in water)

(B) Chemical structure of dyes:

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