DEPARTMENT OF

TEXTILE ENGINEERING
Course Title :Wet
Processing Technology2
Presentation Topic:Briefly
discussion about Azoic Dye

Group-D

1.BTX130100265
2.BTX130100258
3.BTX130100256
4.BTX130100285

Submitted To:
Md.Tanjim Hossain

Azoic dye
Azoic Dyes are also called as Azoic or
Napthol Dyes. These
AZO Dyes
consist a group i.e. called AZO group
having two nitrogen atoms and this group
(covalent bond) connects atomic ring
compounds. The two Nitrogen atoms are
bonded with each other and form -N=Nas part of their molecular structure. Azoic
Dyes are found mainly in three colors and
these are red, brown and yellow.

Another name of Azoic dye

Built in Dye
Magic Color
Developed Color
Ice color
Napthol Dye

History
Azo chromophores were first discovered in
1863 when Martius and Lightfoot coupled
diazonium ions and amines. Within the
year, Peter Greiss prepared Bismarck
brown, the first azo dye. By the 1880s
numerous other azo dyes, such as para
red and primuline red, were developed.

 Since that time, most modern dyestuffs

have been derived from diazotized
aromatic amines, and hence are
sometimes known as diazo dyes. The
simplest azo dyes are yellow, but
changing the number of chromophores or
the backbone structure can produce red,
violet, blue and even black dyes. Azo dyes
are used as textile colorants, and well as
in industrial paints, printing inks,
varnishes, plastics, crayons and other
products.

Origin
Mid 19th century from Greek azos 'without life'

. In recent years, many high performance

azo pigments have been developed that
meet the stringent lightfastness
requirements required for artwork (Berrie
and Lomax 1997).

Formation of Azoic Dyes

These dyes cannot be applied directly on
the fibers as dyes. Actually, these dyes are
produced within the fibers itself. For this
production, first the fiber is impregnated
with one component of these dyes and
then the fiber is treated in another
component of these dyes. In this way the
AZO dyes are formed. This specialty
makes these dyes very fast to washing
within the fabric market.

 When these dyes are used upon the

cellulose fabric then initially this fabric
starts to suffer from poor rub fastness.
This is due to the deposition of the free
pigments on the surface of the fabric. This
problem can be rectified by boiling the
fabric in soap.

Azoic Colors

Azoic Dyeing Process

AZO Dyeing Process is such a process in
which the insoluble azoic dye is produced
on the or within the fiber. By treating a fiber
with diazoic and coupling components, this
process can be achieved. After adjusting
the dye bath conditions appropriately, the
two above mentioned components react.
From this reaction the required insoluble
AZO dye is produced.

First Stage:Naptholation
Second Stage:Diazotation
Third Stage:Coupling

Step-1:

NaOH
27 degree

ONa

CONH
Sodium Naptholate

Step:2
NH

N Cl

Conc.Hcl

NaNo2

Cl
Fast red TR base Diazo component

CH
Cl
3

CH

Soluble diazonium salt

Step:3
we add sodium naptholate and
soluble diazonium salt

CH3
N=N
ONa

Cl

CoNH
Azoic pigment

Naphthols and Bases

Naphthol is also known as azoic coupling component.
These are acylides are of BON (beta-oxy naphthoic
acid). Various types of naphthols can be Naphthol AS,
Naphthol ASBS, Naphthol ASBR etc.
Base is also known as the Diazotised base. This acts as a
coupling reactant along with the naphthol.
These are nomenclatured on the basis of color e.g. Fast
Red Base.
The purpose of diazotisation is to improve solubility.

Dyeing Process of Azoic Colors

The Dyeing process is carried out in three successive steps,
which are as follows:
Naphtholation
Naphthol is water insoluble. Thus the process of making
insoluble naphthol soluble is known as Naphtholation.

The sodium salt of naphthol obtained above is not very much

stable as CO2 reacts with it water to form carbonic acid and it
converts it to free naphthol form so we should avoid any type of
acidic exposure.

The sodium salt is thus treated with HCHO.

When this methylol compound is exposed to high temperature then it gets converted to methylene
compound and naphthol loses its ability to react with diazotised base.
The naphthols are classified on the basis of substantivity i.e. low and high substantivity naphthols.

Diazotisation
This process involves conversion of the base in
the soluble form i.e. hydrochloride form which
has better solubility.
R-NH2 + HCl
R-NH3+Cl(Fast base)
(Hydrochloride base)
HCl + NaNO2
HNO2 + NaCl
R-NH+3Cl- + HNO2
R-N+=N-Cl
+ 2H2O

..
At higher temperature, diazotized base formed becomes
highly unstable and hence backward reaction starts.
Hence the process is carried out at lower temp.
We add HCl which reacts with NaNO2 to form HNO2,
which helps in diazotisation and reacts with free base to
form hydrochloride form.
These can be slow coupling bases which require little
acidic conditions and fast coupling bases which require
stronger acidic conditions.

Coupling
The naphtholated fabric is passed through the diazotised
base solution for coupling reaction to take place.
This process of coupling is highly exothermic and hence
should be carried at low temp.
It also requires acidic conditions i.e. it requires 5-6 pH.
The CH3COOH besides maintaining the pH also acts as a
buffer to maintain the alkalinity of the solution constant.

Coupling Reaction

Some of the naphthol comes out of the fabric and reacts

with the diazotised base to give the azoic pigment which
reduces the washing fastness. Hence, strong soaping is
done to prevent the surface dye.
Moreover, azoic colors are not used as the process of
applying these dyes is very cumbersome.

Types of AZO dyes in accordance to

there nature
A. hazardous AZO-dyes
B. non-hazardous or safe AZO-dyes

Hazardous AZO-dyes

These dyes use AZO-groups as coloring agent,

upon cleavage these chemical groups release
amines, which are harmful,
they are used mostly for cotton dyeing,
cheapest alternative to reactive dyes ( best
industrial dye ),
good color fastness, dyeing process short and
easy,
pollute waste-water with heavy metals,
many AZO-dyes are subject to ISO 14000
legislation

B. non-hazardous or safe AZO-dyes

Availability:
...of product:
1. not easy to purchase
2. not widely distributed
3. they are sold by weight and price is higher
then hazardous azo dyes
...of information:
1. information available in English, using
international standards

Some Examples
naphthol, beta naphthol pigment, para
red, Lithol red, arylide, diarylide, nickelazo, disazo pigment,
and benzimidazolone

Advantages and Disadvantages

Advantages of azoic dyes
Available in bright shades mostly deep red, yellow
and orange.
Brilliant shape of colour
Vary from poor to excellent fastness to to light.
Fastness to washing, perspiration good to
excellent.
Disadvantages of azoic dyes
Heavy shades have poor fastness to crocking.
High costly

 Printing process:The naphtholated fabric is prepared

then it is printed with base printing paste by block
and screen printing method.
After treatment :After printing the printed fabric is
dried at 100105 for 510 minute in a dryer.

If the naphtholation process is not so

sufficient. Then the printing becomes
uneven.