doi: 10.1111/j.1478-4408.2009.00195.

Modified 2,4-difluoro-5-chloro-pyrimidine
dyes and their application in ink-jet
printing on wool fabrics
M Clark,* K Yang and D M Lewis
Department of Colour Science, University of Leeds, Leeds LS2 9AL, UK
Email: m.clark@leeds.ac.uk

Received: 24 February 2009; Accepted: 6 May 2009

This paper describes the modification of three commercially available 2,4-difluoro-5-chloropyrimidine

dyes (Drimarene Brilliant Red K-4BL, Drimarene Brilliant Blue K-BL and Drimarene Golden Yellow K-2R)
by the reaction of the parent dye with 4-hydroxybenzensulphonic acid sodium salt. Capillary
electrophoresis was used to monitor both the course of the above reaction and to ascertain the dye
stability of the dyes in an ink formulation. Inks prepared from the modified dyes showed much higher
storage stability compared with the parent dye-containing inks; this was confirmed by capillary
electrophoresis analysis. Inks containing the modified dyes were printed on wool fabrics and
diffusion ⁄ fixation achieved by ‘batching’ the prints at 25 C; high fixation values were obtained for all
three modified dyes. These prints exhibited excellent colour fastness to washing, rubbing and light, the
former test confirming a high degree of dye–fibre covalent bonding.

Introduction 4-hydroxybenzensulphonic acid sodium salt (HBSA), in the

Ink-jet printing is rapidly becoming a promising printing
technique for textile coloration [1,2]; the method has
many advantages compared with the traditional screen-
printing method. It enables mass customisation, which is
one of the main driving forces for the development of
ink-jet printing on the textile market [3]. For the
traditional printing method, the colours that can be
obtained are limited; while, for ink-jet printing, various
colours can be obtained through the mixing of cyan,
magenta, yellow and black. Ink-jet printing can respond
to market fashion changes very quickly, whereas
traditional screen-printing normally takes 2–8 weeks of
planning before bulk production because of the screen
design, colour mixing and sampling processes. Ink-jet
printing can save a lot of time, especially if only a short
print run is required [4,5]. In traditional screen-printing,
the amount of printing paste used is ca. 200 g ⁄ m2 and a
significant amount of dye must be washed off from the
screens, which is expensive and produces coloured
effluent leading to environmental concerns. Ink-jet
printing uses considerably less ink (ca. 20 ml ⁄ m2) which
eases the environment pollution problem significantly [4].
However, ink-jet printing has some disadvantages
compared with the traditional screen-printing method.
For example, screen-printing can be carried out at a speed
of 50 m ⁄ min or even higher, whilst the highest available
printing speed for ink-jet is only 230 m2 ⁄ h at 600 dpi.
The ink used for textile ink-jet printing costs ca. £100 ⁄ l,
which is quite expensive; fabric pretreatment is required
for ink-jet printing as many components required for
image definition, achieving good dye fixation, colour yield
and colour fastness cannot be incorporated in the ink [6].
In this work, ink used for ink-jet printing on wool
fabrics has been explored through a series of modified
Drimarene K dye-based inks that exhibit excellent stability,
a high degree of dye–fibre covalent bonding and good
colour fastness. The agent used to modify the dye is
dye–fibre reaction, this then becomes the leaving
group, rather than halogen; the advantages targeted by
replacing the halogen with HBSA include higher aqueous
solubility and greater print-ink stability. Some work
on incorporating this leaving group into the activated
heterocycles used for reactive dyes has been reported in the
patent literature [7,8], but it appears that our approach in
modifying the 2,4-difluoro-5-chloropyrimidine (FCP) dyes
is quite novel.
Experimental
Materials
Non-chlorinated worsted wool fabric (200 g ⁄ m)2) was
provided by the Woolmark Company (UK); scoured,
bleached, non-mercerised plain weave cotton fabric
(100 g ⁄ m)2) was provided by Whaleys (UK).
The non-ionic surfactant, Sandozin NIE, and the FCP
dyes used in this study, Drimarene Brilliant Red K-4BL,
Drimarene Brilliant Blue K-BL and Drimarene Golden
Yellow K-2R, were kindly supplied by Clariant
(Switzerland). All other chemicals used in this work were
laboratory grade as received from Sigma-Aldrich (UK).
Purification of Drimarene K dye
The commercial Drimarene Brilliant Red K-4BL was
purified to determine the typical dye content using a
precipitation method according to the following steps: (i)
the commercial dye (20 g) was dissolved in distilled
water (100 cm)3) to make a saturated solution; (ii)
sodium thiocyanate (20% w ⁄ v) was added to precipitate
the dye; (iii) the dye mixture was filtered under suction;
(iv) the filter cake thus obtained was washed with sodium
thiocyanate solution (100 cm)3, 20% w ⁄ v) twice; (v) the
solid dye was washed with acetone (200 cm)3) until there
was no thiocyanate shown to be present by Fourier
transform infrared (FT-IR) spectroscopy (thiocyanate

184 ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190

anion can be detected by FT-IR because it shows a strong
peak at 2067 cm)1); (vi) the precipitated dye was dried in
a vacuum desiccator at ambient temperature.
Ink-jet printing procedure
The textile ink-jet printing requires the following
processes: fabric pretreatment, ink-jet printing, fixation
and washing off.
Wool pretreatment
The wool fabrics were scoured using a solution
containing 1 g ⁄ dm)3 Sandozin NIE and 2 g ⁄ dm)3 sodium
bicarbonate at 50 C for 15 min, rinsed with cold water
and then air-dried before being padded with the
pretreatment solution.
Scoured wool fabric was padded at 100% wet pick-up on
a Werner Mathis (Switzerland) HVF padder with the
pretreatment solution containing 20 g ⁄ dm)3 sodium
metabisulphite, 20 g ⁄ dm)3 thickener carboxymethyl
cellulose, 300 g ⁄ dm)3 urea and 5 g ⁄ dm)3 Alcopol O 60
(Huntsman, UK) and then dried at 60 C.
Ink-jet printing
The ink-jet printing was carried out on an HP Apollo P-
1200 desktop printer at 600 dpi using the ink formulated
according to the recipe: 100 g ⁄ dm)3 Drimarene K dye,
300 g ⁄ dm)3 N-methylmorpholine N-oxide, 20 g ⁄ dm)3 2-
pyrrolidone and 25 g ⁄ dm)3 propan-2-ol [9].
The ink was made up to 1 dm3 with distilled water and
buffered to pH 7.0 using phosphoric acid. The dyes used
in this study were of commercial grade dye and were not
purified unless otherwise indicated.
Fixation
The printed fabric was batched at 25 C under moist
conditions, which were provided by interleaving with a
moist cotton fabric padded with distilled water at a wet
pick-up of 100%.
Washing off
The printed, batched wool fabric was washed with cold
water until no colour could be removed; hot washing was
carried out on a Roaches Pyrotec-S temperature dyeing
machine (Roaches, UK) with a solution containing
2 g ⁄ dm)3 Sandozin NIE and 5 g ⁄ dm)3 sodium bicarbonate
(NaHCO3) at 60 C for 15 min, after which the fabric was
rinsed again in running tap water for 10 min.
Modification of the Drimarene K dye
Drimarene K contains the 2, 4-difluoro-5-chloropyrimidine
reactive group which is able to react with 4-hydroxy-
benzensulphonic acid sodium salt by a nucleophilic
substitution reaction mechanism (Scheme 1).
H H
D N N F
N + HO
Cl
F F
Scheme 1
ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190
14784408, 2009, 3, Downloaded from https://onlinelibrary.wiley.com/doi/10.1111/j.1478-4408.2009.00195.x by Egyptian National Sti. Network (Enstinet), Wiley Online Library on [30/10/2023]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License
Clark et al. Ink-jet printing on wool fabrics
The carbon atom in position 2 is more electrophilic and
accessible to nucleophilic substitution than is the carbon
atom in position 4, partly because of the two adjacent,
electron-withdrawing nitrogen atoms. When the fluorine
in position 2 is substituted, the reactivity of the system
decreases, so it is difficult for the fluorine in position 4 to
be substituted.
Capillary electrophoresis showed that, with increasing
reaction time, the area of the separated peak
corresponding to the parent FCP dye decreased, while the
component peak attributed to the modified dye increased.
CE was therefore used to monitor the progress of the
modified dye synthesis.
Analytical techniques
Capillary electrophoresis
Capillary electrophoresis (CE) is a technique which can be
used to identify the components in a solution according
to their different mobilities; mobility in the electric field
depends on component size ⁄ mass-to-charge ratio.
The CE equipment (Dionex, USA) used in this study has
a fused silica capillary with an internal diameter of 50 lm
and a length of 47 cm from injection point to detector. The
voltage power applied was 20 kV and the buffer employed
was 10 mM potassium dihydrogen phosphate at pH 9.0
adjusted using 1 M sodium hydroxide.
When high voltage is applied, the cations migrate to the
cathode and carry the bulk solution, a phenomenon termed
electroosmotic flow (EOF). In the case of positively charged
components, their electrophoretic mobility is in the same
direction as the EOF, so they arrive at the detector quickly;
in the case of negatively charged components, their
electrophoretic mobility lies in the opposite direction to
the EOF, hence their arrival at the detector is retarded.
Neutral components are not affected by the electric field
and so they arrive at the detector with the EOF front [10].
Ultraviolet–visible spectrometer
The ultraviolet–visible (UV–vis) absorbance of the dye in
aqueous solution was measured using a Perkin Elmer
Lambda 40 UV–vis Spectrometer (UK) in order to
calculate dye concentration in the various wash-off
solutions and thus to determine fixation (degree of dye–
fibre covalent bonding). Two identical printed fabrics
with a size of 20 · 8 cm at 600 dpi were used to calculate
the per cent fixation: one was washed off immediately
after printing to obtain the total amount of the dye
printed on the fabric and the solution was diluted to
500 cm)3; the other one was used for batching followed
by washing to obtain the amount of the dye washed off
after the fixation process and the washing solution was
diluted to the same volume of 500 cm)3. The absorbance
of the printed dye solution A0 and absorbance of the
D N N O SO3Na
SO3Na N
Cl
185

Clark et al. Ink-jet printing on wool fabrics
wash-off solution A at the wavelength of maximum
absorption kmax were used to obtain the per cent fixation
(%F) according to Eqn 1.
% F ¼ ðA0  AÞ=A0  100
Colour fastness test
Colour fastness performance was assessed using the
Woolmark Test Method 250 (washing fastness test);
Woolmark Test Method 165 (rubbing fastness test)
and Woolmark Test Method 5 (light fastness test) [11–13].
Results and Discussion
Rationale of sodium metabisulphite in the wool
pretreatment
There are three functional groups in the wool fibre, i.e. thiol
(SH), amino (NH2) and hydroxy (OH), that can react with
the reactive dye. The cysteine thiol group is much more
nucleophilic compared with the amino group, followed by
the hydroxy group unless disulphide bonds are cleaved.
Reactive dye, even when applied by conventional
‘exhaust’ methods at pH 5–6, reacts preferentially with
cysteine thiol, with a small extent of reaction with lysine-e-
amino; sufficient thiols are formed from the so-called
‘setting’ reaction in which the hydrogen sulphide
eliminated from the small amount of cysteine
present (39 lmol ⁄ g)1) reacts with a plentiful supply of
disulphides to generate new cysteine thiol residues [14,15].
The reducing agent, sodium metabisulphite (Na2S2O5),
included in the wool pretreatment forms sodium
bisulphite in water (Scheme 2); bisulphite generates more
thiol groups because of the reaction between sodium
bisulphite and cystine (Scheme 3). The nucleophilic
substitution reaction between the FCP dye and a cysteine
thiol group is shown in Scheme 4. Therefore, the
inclusion of sodium metabisulphite in the pretreatment is
an effective method of improving the dye fixation and
colour strength of the print by creating more reactive
O O
NaO S S Na
O O
Scheme 2
NH NH
HC CH2 S S CH2 CH + NaHSO3
CO CO
Cystine
Scheme 3
H H
D N N F
+ HS Wool
N N
Cl
F F
Scheme 4
186 ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190
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cysteine thiol groups in the wool by breaking some of the
disulphide bonds crosslinking the wool structure; also, it
is an effective reducing agent which can be used to bleach
the wool and thus reduce any fabric yellowness [16].
ð1Þ
Optimisation of the FCP dye ⁄ HBSA reaction
The commercial Drimarene Brilliant Red K-4BL was
found to have a pure colour content of 55 ± 1% w ⁄ w by
comparison of the absorbance between the commercial
dye and the purified dye at the same concentration at
kmax; the commercial Drimarene Brilliant Blue K-BL and
Drimarene Golden Yellow K-2R were assumed to have the
same purity. The molecular weights of the dyes were
989.15 for Drimarene Brilliant Red K-4BL, 695.97 for
Drimarene Brilliant Blue K-BL and 656.93 for Drimarene
Golden Yellow K-2R.
Dye modification using HBSA was carried out at pH
values of 6.0, 7.0, 8.0, 9.0 or 10.0 and temperature
conditions used were 50, 60, 70 or 80 C; a molar ratio of
dye:HBSA of 1:1, 1:2, 1:3 and 1:4 was used. The reactions
were monitored using CE. The per cent yield of the
HBSA-substituted dye was estimated by calculating the
ratio of the modified dye peak against the starting FCP
dye peak on the electropherogram.
From the various reaction conditions used, it was found
that the optimum condition was to react at pH 8.0, 60 C
and a molar ratio (dye:HBSA) of 1:2, which resulted in 86%
and 90% yield for the blue and red dyes, respectively, after
a 2-h reaction; a yield of 83% can be achieved for the
yellow dye after a 4-h reaction (Figure 1).
The CE electropherograms of parent and modified
Drimarene Brilliant Red K-4BL reacted with HBSA for
different times are shown in Figure 2. It is clear that,
in the first 30 min, the reaction occurred rapidly, the
formation of the new HBSA–dye has shifted the elution of
the parent dye to 9 min (Figure 2b). After 120 min, there
was little parent dye left in the reaction solution. The CE
electropherogram remained unchanged when the reaction
time was extended from 120 to 240 min.
H2O O O
O S H + HO S + 2Na
O O
NH NH
HC CH2 SH + HC CH2 SSO3Na
CO CO
Cysteine
D N N S Wool
Cl
Cysteine
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Clark et al. Ink-jet printing on wool fabrics

100 Ink stability of the FCP dye-based ink and the HBSA
Blue
Red
modified dye-based ink
80 Yellow The inks for both the parent and modified dyes were
formulated according to the ink recipe stated above. As
Yield, %

60 shown in Figures 3 and 4, the HBSA modified dye-based

ink showed excellent stability and there was no change in
40 the CE peak area for this modified dye even after 1 year
of storage. For the parent FCP dye-based ink, the per cent
20 area of the corresponding CE peak decreased from 90% to
23% over the same storage time.
0
0.5 1 2 3 4
Modification using the above method is thus an
Reaction time, hour effective method to increase the ink stability since the
incorporation of the HBSA will decrease the reactivity of
Figure 1 Percentage yield of HBSA substituted dyes vs reaction the dye.
time

(a)
2.42x10–3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes
(b)
1.36x10–3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes
(c)
1.65x10–3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes
(d)
1.58x10–3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes

Figure 2 CE electropherogram of dyes: (a) commercial dye Drimarene Brilliant Red K-4BL; and Drimarene Red K-4BL ⁄ HBSA after
(b) 30-min reaction; (c) 60-min reaction; (d) 120-min reaction

ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190 187
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Clark et al. Ink-jet printing on wool fabrics

(a)
2.10x10–3

AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes
(b)
2.31x10–3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes

Figure 3 CE electropherogram of (a) fresh modified dye-based ink and (b) after 1 year of storage

(a)
1.98x10-3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes
(b)
2.07x10-3
AU

0
0 2.0 4.0 6.0 8.0 10.0 12.0 14.0
Minutes

Figure 4 CE electropherogram of (a) fresh parent dye-based ink and (b) parent dye-based ink after 1 year of storage

100
Dye–fibre covalent bonding efficiency of the modified Blue
Red
dyes following ink-jet printing on wool substrate
80 Yellow
The fixation values (% fixation) obtained following wool
fabric printing with the three modified dyes and batching
Fixation , %

for different times at 25 C are shown in Figure 5. The 60

red dye can achieve 86% fixation after 2 h batching;
corresponding values for the blue and yellow dyes were 40
81% for both dyes after 4 and 5 h batching time,
respectively. In comparison, it was found that the parent 20
dye-based ink produced a fixation of 80% for the blue
dye, 83% for the red dye and 77% for the yellow dye 0
after 4 h batching time, shown in Figure 6. 1 2 3 4 5
Batching time, hour
Initially, the concentration of the dyes in the print
solution is high, but, following diffusion into the wool Figure 5 Per cent fixation values for the modified dyes vs
fibre, a sufficiently large number of reactive wool thiolate batching time

188 ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190
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Clark et al. Ink-jet printing on wool fabrics

100 groups (anionic cysteine groups) become available for

Blue Red Yellow
covalent bonding with the reactive dye. As the extent of
80 covalent reaction increases between dye and fibre, the
remaining concentration of reactive dye in the print
Fixation, %

60
solution decreases, as do the reactive sites on the wool
40 fibres; therefore, the per cent fixation values level off to a
constant value.
20
Colour fastness tests
0 Washing fastness test was carried out according to the
2 4 6 8
Time, hours Woolmark test method 250; the results are shown in
Table 1. The change in shade was small, resulting in a grade
Figure 6 Per cent fixation values for the parent dyes vs batching of 4–5 to 5; there was no staining on the adjacent fabrics,
time except a light staining from the yellow dye on the cotton.
The excellent washing fastness is because of the strong
covalent bonding between the dye and the wool fibre.
Rubbing fastness test was carried our according to the
Table 1 Washing fastness of the modified Drimarene K dyesa
Woolmark test method 165 and the results are shown in
Table 2. The dry rubbing fastness can obtain the maximum
Staining
of 5 for all the modified dyes while the wet fastness varies
Change from 4–5 to 5. The good rubbing fastness is also due to the
Modified dye in shade CA C N P A W
strong covalent bonding of the dye on the wool fibre.
Light fastness was carried out according to the
Red K-4BL 5 5 5 5 5 5 5
Woolmark test method 5, using a QSun 1000 Xenon test
Yellow K-2R 4–5 5 4–5 5 5 5 5
Blue K-BL 4–5 5 5 5 5 5 5 chamber with irradiance of 0.65 W/m2 at a temperature of
45C. The prints for the Modified Drimarene K dyes were
a CA, cellulose acetate; C, cotton; N, nylon 6, 6; P, polyester; A, acrylic; tested to Blue Wool reference nos 5 and 6. As seen from
W, wool Table 3a,b, all of the dyes used in this work can pass
grade 5; moreover, the yellow dye can pass grade 6.
In general, the parent dye-based inks were either the
same grade or 0.5 grade lower when compared with the
Table 2 Rubbing fastness of the modified Drimarene K dyes
modified dye ink prints for all the fastness tests.

Warp Weft
Conclusions
The modification of Drimarene K dyes by reaction with 4-
Modified dye Dry Wet Dry Wet
hydroxybenzensulphonic acid sodium salt is an effective
method to improve their ink-jet printing ink stability. The
Red K-4BL 5 4–5 5 4–5
Yellow K-2R 5 4–5 5 4–5 modified dye-based inks show excellent solubility and
Blue K-BL 5 5 5 5 stability during storage for up to 1 year. Because of the
bisulphite present from the fabric preparation, a high

Table 3 Light fastness of the modified Drimarene K dyes under Blue Wool standard no. 5 (a) and no. 6 (b)

Standard wool reference no. 5

Modified dye Greyscale rating contrast 4 Greyscale rating contrast 3 Mean Action

(a)
Red K-4BL 4+ 3+ 5+ Pass
Yellow K-2R 4+ 3+ 5+ Pass
Blue K-BL 3–4 3 5 Pass

Standard wool reference no. 6

Modified dye Greyscale rating contrast 4 Greyscale rating contrast 3 Mean Action

(b)
Red K-4BL 3–4) 2–3) 6) Fail
Yellow K-2R 3–4 2–3 6 Pass
Blue K-BL 3–4) 2–3) 6) Fail

ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190 189

Clark et al. Ink-jet printing on wool fabrics
degree of fixation was obtained for the printed samples
after 2 h batching at 25 C; this is a big advantage, as the
new process allows ink-jet printing of wool to be carried
out without the need for steaming. The printed samples
show good colour fastness to washing, rubbing and light.
Acknowledgements
This work was carried out through a PhD scholarship
awarded under the China Australia Wool Innovation
Network (CAWIN) project. Funding for this project was
provided by Australian wool producers and the Australian
Government through Australian Wool Innovation Limited.
References
1. T L Dawson and C J Hawkyard, Rev. Prog. Color., 30 (2000) 7.
2. M Fryberg, Rev. Prog. Color., 35 (2005) 24.
3. M T Fralix, J.T.A.T.M., 1 (2001) 1.
4. J Provost, Ink Jet Printing on Textiles, (available at: http://
users.ecs.soton.ac.uk/rnt/microflex/, last accessed 15 April
2008).
190 ª 2009 The Authors. Journal compilation ª 2009 Society of Dyers and Colourists, Color. Technol., 125, 184–190
14784408, 2009, 3, Downloaded from https://onlinelibrary.wiley.com/doi/10.1111/j.1478-4408.2009.00195.x by Egyptian National Sti. Network (Enstinet), Wiley Online Library on [30/10/2023]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License
5. L Nicoll, in Digital Printing of Textile, Ed. H Ujiie
(Cambridge: Woodhead Publishing Limited, 2006) 201.
6. J Provost, M Frenche, U Hees, M Kluge and J Weisre, in
Textile Ink Jet Printing, Eds T L Dawson and B Glover
(Bradford: SDC, 2004) 57.
7. FR1283172 (ICI; 1962).
8. H A Riehen, H F Bottmingen and H M Riehen, CH464396
(Geigy; 1968).
9. D M Lewis and P J Broadbent, Proc. SDC Col. Conf., Belfast,
UK (2006).
10. K D Altria, Capillary Electrophoresis Guidebook: Principles,
Operation, and Applications (USA: Humana Press, 1995).
11. Woolmark Test Method 5: Colour Fastness to Light (Australia:
Woolmark, 2000).
12. Woolmark Test Method 250: Colour Fastness to Hand
Washing (Australia: Woolmark, 2002).
13. Woolmark Test Method 165: Colour Fastness to Rubbing
(Australia: Woolmark, 2002).
14. M T Pailthorpe, in Wool Dyeing, Ed. D M Lewis (Bradford:
SDC, 1992) 57–58.
15. D M Lewis and I Seltzer, J.S.D.C., 88 (1972) 327.
16. D M Lewis, in Wool Dyeing, Ed. D M Lewis (Bradford: SDC,
1992) 116.