GROUP MEMBERS:

MD. RASEL MIAH

MD. JAHIDUL HASAN
MD. SAYEDUR RAHMAN
MD. RABIUL AUWAL BHUIYA
MD. SAWNOWER HOSSAIN
MD. ZIAUR RAHMAN
SAWDAGOR RUPAYAN
Table of content:
 Introduction
 Contribution of azo group
 The reaction in the manufacture of azo-
colorants:
 Azo group containing dyes:
 Stability of azo linkage
 Aromatic amines which may be considered
carcinogenic:
 Health effect in azo colorants
 Prevention of carcinogenic effect of azo group
 Conclusion
 Introduction
 Azo group is the most important group for colour
formation.Which form bridges between two or more
aromatic rings and form colour component.
The part of an azo (-N = N-) colorant molecule is a double
bonded azo linkage.

The azo linkage consists of two nitrogen atoms, which are

also linked to carbon atoms. At least one of these carbon
atoms belongs to an aromatic carbocycle, an aryl moiety,
usually benzene or naphthalene derivatives or a
heterocycle, e.g. pyrazolone, thiazole. The second carbon
adjoining the azo group may also be part of an aliphatic
derivative, e.g. acetoacetic acid.
In general, an azo colorant molecule can be summarised as
follows:
aryl - N = N - R,
Contribution of azo group
 Azo colorants have one or more chromophoric groups in
their chemical structure and therefore are capable of
colouring diverse substances by selective reflection of
daylight. Azo colorants include both azo dyes and azo
pigments.

 Azo colorants range in shade from greenish yellow to

orange, red, violet and brown. However, the important
disadvantage limiting their commercial application is
that most of them are red and none are green.
 The
  reaction in the manufacture of azo-colorants:

  diazotization +
     coupling  

R - NH2  → R - N = N] Cl –
  → R - N = N - 
R’
  HCI,NaNO2     R’-H,NaOH  

aromatic    diazonium   coupling- azo-

amine colorant
diazo    compound   component  
component
Azo group containing
dyes:
The majority of industrial important azo dyes
belongs to the following groups:
 Acid dyes
 Basic dyes
 Direct dyes
 Disperse dyes 
 Mordant dyes
 Reactive dyes
 Solvent dyes
Cont.
 Acid dyes:
Acid dyes are the most widely used azo dye in Europe.
The dyes are manufactured and employed as water-
soluble sodium salts of the sulfonic or carboxylic acid
groups.
Some of the basic azo dyes are used in medicine for treatment of 
bacterial infections
 Direct dyes:
Direct dyes include water-soluble anionic azo dyes,
which require the presence of electrolytes for the dyeing
process. Most of the direct dyes are benzidine-based.
They are classified as direct dyes, because they may be
applied directly to celluloid fibres.
 Cont.
 Disperse dyes:
Disperse dyes encompass azo dyes, which are
sparingly soluble in water and mainly used for dyeing of
synthetic . The disperse dyes are clearly the dominating
group within azo dyes used world-wide.

 Mordant dyes:
Mordant dyes include azo dyes, which are converted
into their final, insoluble form on the fibres. A mordant
is a metal, most commonly chromium, aluminium,
copper or iron. The application area is limited to the
colouring of wool, leather, furs and anodised
aluminium.
Cont.
 Reactive dyes:
Reactive dyes encompass azo dyes, which form
covalent bonds with the fibres they colour, e.g. cotton,
rayon, cotton, wool silk and nylon. The dye molecule
contains specific functional groups, which can undergo
addition or substitution reactions with the -OH, -SH and
-NH2 groups present in the fibres.
 Solvent dyes:
They are used for coloration of inks, plastics (mainly for
polystyrene and resins of polymethacrylate), wax and
fat products and mineral oil products (gasoline, fuels
lubricants and greases
Cont.
 Azo pigments:
Pigments are widely used. The most important
area of use is in the graphic printing inks,
where approximately 50% of all pigments are
used. 25% of the pigments are used in paints
and coatings and less than 20% in plastics and
fibres. The remaining application fields are e.g.
textile printing, office articles, wood, paper,
cosmetics and food and feed colouring.
Stability of azo linkage
 The azo linkage is considered the most labile portion of
an azo dye. The linkage easily undergoes enzymatic
breakdown, but thermal or photochemical breakdown
may also take place. The breakdown results in cleavage
of the molecule and in release of the component
amines.
 The component amines which may be released from azo
dyes are mostly aromatic amines (compounds where an
amine group or amine-generating group(s) are
connected to an aryl moiety). In general, aromatic
amines known as carcinogenic
Aromatic amines which may be
considered carcinogenic:

Name of amine:
 2-Naphtlmylanime
 3,3’-Dichlorobenzidine
 3,3’-Dimethoxybenzidine
 (p-(phenylazo)-aniline)
 4,4’-Methylenebis(2-chloroaniline) (MOCA)
 4,4’-Methmylenedianiline
 4,4’-Oxydianiline
 4,4’-Thiodianiline
 4-Chloro-o-toluidine
 4-Methoxy-m-phenylenediainine
Cont.
 6-Methoxy-m-toluidine
(5-methyl-o-anisidine)
 o-Toluidine
 p-Aminoazobenzene
 3,3’-Dimethylbenzidine
 4,4’-Methylenedi-o-toluidine
 4-Methyl-m-phenylenediamine
(2,4-diarninotoluene
 o-Aminoazotoluene
 o-Anisidine
 p-Chloroaniline
 Health effect in azo colorants
 Cancer and allergy :
Aromatic amines which release amines are carcinogenic which are responsible
for cancer and allergy. The following dyes are responsible for cancer and
allergy:
 Disperse Black 1
 Disperse blue 1
 Disperse blue 35
 Disperse blue 106
 Disperse blue 124
 Disperse orange 37/76
 Disperse red 1
 Disperse Orange 3
 Disperse Orange 76
 Disperse Red 17
 Disperse Yellow 3
 Disperse Yellow 9
 C.I. Disperse Orange 3
 p-aminoazobenzene

Prevention of carcinogenic effect of
azo group

 To avoid the bad effect of azo

group the concentration (mg/kg) of
each harmful aromatic amine in
dye products should not exceed
150 mg/kg.
Conclusion
Allthough some azo group consisting
compound have some bad effect but
it is very important group for colour
formation. Most of the colour
component are consist of azo group.
It’s proper utilization can avoid it’s
bad effect. For this reason as a textile
engineer we should know details
about it.