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“History”

Reactive dyes first appeared commercially in 1956, after their


invention in 1954 by Rattee and Stephens at the Imperial Chemical
Industries Dyestuffs Division site in Blackley, Manchester, United Kingdom
• Various developments – including new chemical types
• 1980’s Mixed bifunctional dyes (esp. Sumitomo – Sumifix Supra dye

“About Reactive Dye”


Reactive dyes are used to dye cellulosic fibres. The dyes
contain a reactive group, either a haloheterocycle or an activated double
bond, that, when applied to a fibre in an alkaline dye bath, forms a chemical
bond with an hydroxyl group on the cellulosic fibre. Reactive dyeing is now
the most important method for the coloration of cellulosic fibres. Reactive
dyes can also be applied on wool and nylon; in the latter case they are
applied under weakly acidic conditions. Reactive dyes have a low utilization
degree compared to other types of dyestuff.

General Features of a Reactive Dye Molecule:

W = water solubilising group


D = chromophore
B = bridging group
RG = reactive group
X = leaving group
“Types of Reactive Dyes”

1. Sulphatoethyl sulphone dyes:


O NH2
SO3Na

O N
H

SO2CH2CH2OSO3Na

Vinyl sulphone dye (Remazol Brilliant Blue R, C.I. Reactive Blue 19)

2. Monochloro-s-triazine dyes:
Cl

SO3Na N N

OH HN N N
N H
N

NaSO3 SO3Na

Monochloro-s-triazine dye (Procion Red H-3B, C.I. Reactive Red 3)


3. Bis (monochloro-s-triazine) dyes:
Cl Cl

SO3Na N N N N NaSO3

OH HN N N N N NH OH
N H H N
N N

NaSO3 SO3Na NaSO3 SO3Na

Bis(monochloro-s-triazine) dye (Procion Red HE-3B, C.I. Reactive Red 120

4. Mixed Bifunctional reactive dyes:


Cl
N
Dye NH N
N
N
H

General structure of Sumifix Supra dyes


SO2CH2CH2OSO3Na
MCT-SES or MCT-VS
[Reactron Supra F dyes are similar
“Reactions of Reactive Dyes”

Nucleophilic addition:

H H
O - NaHSO O
4
DYE S C C OSO3Na DYE S CH CH2
O H H O

O H - O
- +Cellulose O +
DYE S CH C O Cellulose DYE S CH CH2
O H O

H2O

O H H
DYE S C C O Cellulose + OH-
O H H

ß-elimination of ß-sulphatoethylsulphone to vinyl sulphone and reaction


with cellulose.
Nucleophilic substitution:
Cl
N
Dye N N
H
N
Cl Cl
.. O Cellulose
N N
+ X- - Cl -
Dye N N Dye N N OR
H H
N N Cl
Cl X Cl
N
Dye N N
H
N
OH

Competing nucleophilic substitution reactions of s-triazine dyes

“Application Methods”
• Continuous:
– eg. Pad - Thermofix

• Semi-Continuous:
– eg. Pad - Batch

• Batchwise Exhaustion:
– eg. Winch, Jet, Package and Beam Dyeing

• Printing:
– eg. Print - Thermofix
Advantages:
• Full Colour Gamut
• Brilliant, bright colours
• Colvalent fixation à high WashFastness (WF)
• Varying reactivities
– Various temperatures
including low energy (cold dyeing)
• Various methods of application
• Inexpensive to apply (but dyes expensive)

Disadvantages:
• Incomplete fixation (problem with hydrolysis)
• Need for wash-off (for high WF)
• Need for high concentrations of salt
– Affect natural balance of watercourses
• High pH
• Some dyes are “AOX” – potentially harmful to the environment
“Hot And Cold Dyeing Brands”

Cold Dyeing Brand:


Reactive Cold Brand Dyestuffs are fibre reactive
dyes which form a chemical linkage with Hydroxyl groups of Cellulose and
thus give dyeing and printing good fastness to wet treatments.

Hot Dyeing Brand:


He Dyes are Reactive Dyes for Cellulosic material and
designed to give high fixation by exhaust dyeing method when applied at the
temperature 75ºC - 95ºC.

The other misconception that people have is that they assume


the Hot dye is more colour-fast than the Cold one because you have boiled
the colour in. This is not so. Cold dyes are more robust and colours will
remain brighter for longer than Hot dyes. The cooler process is not only a
little easier, it is also more lasting.

Cold reactive dyes are very reliable and used throughout the global clothing
and textile industries to permanently colour fabrics made from plant fibres.
The dyes react with the fibre on a molecular level to produce a permanent
bond that withstands wash after wash. The colour becomes part of the fabric.