Azo dye

Azo dyeing is a technique in which an insoluble azo dye is produced directly onto or within the fibre. This is
achieved by treating a fibre with both diazoic and coupling components. With suitable adjustment of dyebath
conditions the two components react to produce the required insoluble azo dye. This technique of dyeing is
unique, in that the final colour is controlled by the choice of the diazoic and coupling components.

Azo compounds generally have a molecular formula of the form R-N=N-R', in which R and R' can be either
aromatic or aliphatic. The N=N group is called an azo or diimide functional group. The aromatic groups help to
stabilise the N=N group by making it part of an extended delocalised system. This also has the effect of making
many azo compounds coloured, as delocalised or conjugated systems often absorb visible frequencies of light.

A typical Azo compound, chrysoidine dye

Another typical Azo compound, 4-hydroxyphenylazobenzene, a.k.a. yellow azo dye

The name azo comes from azote, an old name of nitrogen that originates in French and is derived from the
Greek a (not) + zoe (to live). Aromatic azo compounds (R = R' = aromatic) are usually stable and have vivid
colors such as red, orange, and yellow. Therefore, they are used as dyes, which are called azo dyes. Some azo
compounds, eg. Methyl orange, can also be used as acid-base indicators, due to their ability to function as weak
acids, and the different colours of the acid and salt forms. Azobenzene is another typical aromatic azo
compound. Their colour originates from absorbance in the visible region of the spectrum due to the
delocalisation of electrons in the benzene and azo groups forming a conjugated system, whereby the N=N group
is the chromophore.

Aliphatic azo compounds (R and/or R' = aliphatic) are rather unstable. At an elevated temperature or by
irradiation, two carbon-nitrogen (R-N) bonds are cleaved simultaneously with the loss of nitrogen gas to
generate carbon-centered radicals.

Aromatic azo compounds can be synthesized by using an azocoupling reaction, that is, an electrophilic
substitution reaction on aromatic rings with diazonium salts. Diazonium salts decompose at temperatures
warmer than about 5 degrees Celsius, so the reaction must take place in solution under freezing conditions: