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Reactive Dyes
Dr Kelvin N Tapley Department of Colour Chemistry University of Leeds, Leeds, UK
September 2003
Outline
History General Features Advantages & Disadvantages Factors influencing performance Common Types of Reactive Dyes Reactions of Reactive Dyes Application Methods Summary
History
Cyanuric chloride reaction with cotton and then amines Remazol (vinyl sulphone) chemistry intorduced 1956 Rattee + Stephen (ICI) first reactive dyes
chlorotriazines
Various developments including new chemical types 1980s Mixed bifunctional dyes (esp. Sumitomo Sumifix Supra dyes)
W = water solubilising group D = chromophore B = bridging group RG = reactive group X = leaving group
Advantages?
Full Colour Gamut Brilliant, bright colours Colvalent fixation high WashFastness (WF) Varying reactivities
Various temperatures including low energy (cold dyeing)
Disadvantages?
Incomplete fixation (problem with hydrolysis) Need for wash-off (for high WF) Need for high concentrations of salt
Affect natural balance of watercourses
Transfer of colorants to adjacent fabrics leads to staining problems NB some of the WF tests have got tougher!
During the laundry process the fabric is subjected to some severe conditions and very often dye is beaten from the fabric. This results in dye entering the washing liquors. Once in the washing liquors 3 things can happen to the dye... 1. Re-adsorb onto original fibre 2. Adsorb to a different substrate 3. Remain in the wash liquor
+ +
Reactive dye
Linear / planar structure (shape) Other functional groups present Realtive positions of functional groups (incl. reactive groups) Plus characteristics and quantity of impurities / additives
Pre-treatment PreIt is easy to appreciate that what happens to the fabric before dyeing will affect dyeing itself ! Pre-treatment is crucial to a dyer if he wants to achieve rightPrerightfirst-time dyeings. After pre-treatment he can trust his fabric. firstprefabric.
Scouring
Essentially cleaning! removal of waxes, fatty acids etc. Scoured
Exhaustion
Unscoured
Time
Definition of scour: To remove natural impurities, dirt or grease from (cloth or fibers) by means of a detergent.
N H SO2CH2CH2OSO3Na
Vinyl sulphone dye (Remazol Brilliant Blue R, C.I. Reactive Blue 19)
Monochloro-s-triazine dyes
Cl SO3Na N OH HN N N N N N H
NaSO3
SO3Na
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NaSO3
SO3Na
2,4-difluoro-5-chloro-pyrimidine dyes
F N N H Cl N F
H OH N
SO3Na
2,4-difluoro-5-chloro-pyrimidine dye (Levafix Brilliant Red E 3BA, C.I. Reactive Red 147)
11
2,4,5-trichloro-pyrimidine dyes
Cl SO3Na N N NaSO3 SO3Na
Trichloro pyrimidine dye (Drimarene Red Z 2B, C.I. Reactive Red 17)
Cl OH HN N
N Cl
Cl N
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Nucleophilic addition
Reactive group
SO2 - CH = CH2
Sulphone (SO2)
13
Nucleophilic addition
O DYE S O H C H H C H OSO3Na - NaHSO 4 DYE O S O CH CH2
O DYE S O
H CH C H H2O O Cellulose
+ Cellulose
O DYE
O S O CH
+ CH2
O DYE S O
H C H
H C H O Cellulose
OH-
Nucleophilic substitution
Reactive group
Cl N
N N
Cl
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Nucleophilic substitution
Cl N Dye Cl N Dye N H N N Cl .. + XN Dye N H N N X N Dye N H N N OH Cl Cl - ClOR Cl N H N N O Cellulose
Separation of bis-Monochlorotriazinyl Reactive Dyes and Hydrolysates in Dyehouse Effluent by Capillary Zone Electrophoresis
0.43 0.33 0.23 0.13 0.03 6 10 14 Time / minutes 18 22
15
Application Methods
Continuous
eg. Pad - Thermofix
Semi-Continuous
eg. Pad - Batch
Batchwise Exhaustion *
eg. Winch, Jet, Package and Beam Dyeing
Printing
eg. Print - Thermofix
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Summary
Dominant dye class for cotton Importance of nature and number of reactive groups ( covalent fixation) Different types/chemistries
many different application methods
Acknowledgements
Department of Colour Chemistry, University of Leeds DFID
K.Tapley@leeds.ac.uk
www.leeds.ac.uk/ccd
Department of Colour Chemistry, University of Leeds, Leeds, LS2 9JT
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Questions ?
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