European Polymer Journal 36 (2000) 2505±2511

Modi®cation of cotton by acrylic acid (AA) in the presence of

NaH2PO4 and K2S2O8 as catalysts under thermal treatment
Premamoy Ghosh a,*, Debasish Das a,b
a
Department of Polymer Science and Technology, University of Calcutta, 92, Acharya Prafulla Chandra Road, Calcutta 700 009, India
b
Institute of Jute Technology, 35, B.C. Road, Calcutta 700 019, India
Received 12 May 1998; received in revised form 10 January 2000; accepted 20 January 2000

Abstract
Cotton fabric was modi®ed using acrylic acid (AA) as the ®nishing agent in the presence of K2 S2 O8 and NaH2 PO4
catalysts separately or in selected combinations, employing a pad-dry-cure technique. Treatment with 8% AA at 30°C
and at pH 7 produced optimum e€ects: a batching time of 30±45 min at 30°C followed by drying of the batched fabric at
95°C for 5 min and curing of the dried fabric at 140°C for 5 min produced most balanced improvements in the textile
related properties. NaH2 PO4 catalyst allowed esteri®cation of AA with the cellulosic constituent of cotton, and K2 S2 O8
catalyst allowed radical polymerization of free-AA or cotton bound AA moieties, ultimately leading to some degree of
crosslinking of the chain polymers of cotton. Examination of the surface morphology of untreated and treated cotton
fabrics by scanning electron microscopy revealed a good degree of masking of the convolutions of the cellulosic ®bres
and surface crack by a cohesive ®lm of poly(acrylic acid) or its salt, particularly when K2 S2 O8 was used either alone or
in combination with NaH2 PO4 as catalyst. Ó 2000 Elsevier Science Ltd. All rights reserved.

Keywords: Acrylic acid; Finishes on cotton cellulose; Crosslinking of cellulose; Esteri®cation

1. Introduction But ®nishes based on such non-polymeric poly(carb-

Finishing of cotton textiles using resins from me-
thylolated-urea/urea-derivatives such as dimethylol di-
hydroxyethylene urea (DMDHEU) results in some odd
disadvantages in respect of relatively poor tenacity re-
tention, abrasion resistance and lowering in whiteness
index despite signi®cant improvement in wrinkle recov-
ery [1]. Such methylolated resin ®nishes are associated
with the disadvantage of formaldehyde splitting during
processing and use endangering the health of processors
and users [1,2]. Use of poly(carboxylic acid) such as
butane tetracarboxylic acid and cyclopentane tetra-
carboxylic acid etc. as substitute ®nishing agents appears
to be much more prospective in this respect [2±4] in view
of their environment friendly and nontoxic character.
*
Corresponding author. Tel.: +91-33-351-0597; fax: +91-33-
351-3222.
E-mail address: png@cucc.ernet.in (P. Ghosh).
oxylic acid) cannot much improve tear strength,
abrasion resistance, sti€ness and moisture regain char-
acteristics of cotton fabrics. It is therefore considered
that chemical modi®cation of cotton by a combination
of (a) esteri®cation, (b) chain polymerization and (c)
ultimate crosslinking consequent to application of a
monomeric readily polymerizable acid such as acrylic
acid (AA) (CH2 @CHCOOH) under the in¯uence of
appropriate catalysts may turn out to be more pro-
spective in respect of all-round property improvement or
improved property balance. Results of related studies
are reported in the present paper.
2. Experimental
2.1. Materials
Ex-powerloom, mill bleached, plain weave cotton
fabrics with 262 ends/dm, 315 picks/dm, 13 tex warp and

0014-3057/00/$ - see front matter Ó 2000 Elsevier Science Ltd. All rights reserved.
PII: S 0 0 1 4 - 3 0 5 7 ( 0 0 ) 0 0 0 2 8 - 8
2506 P. Ghosh, D. Das / European Polymer Journal 36 (2000) 2505±2511
15 tex weft and having an average area density of 106 g/
m2 was used for the present study.
Commercial grade AA, monomer obtained from E.
Merck, India was used without any treatment or puri-
®cation. All other chemicals used were of laboratory
reagent grade.
2.2. Methods
2.2.1. Desizing and scouring of mill bleached cotton cloth
In order to remove the sizing chemicals from the
surface of the mill bleached cotton cloth, the latter was
desized and scoured prior to chemical modi®cation.
Desizing of the bleached cotton fabric (250±300 g)
was performed in a 10 l steel bowl using a 0.25 N HCl
solution at the temperature of 50°C for 2 h at a fab-
ric:liquor ratio of 1:20 (w/v). The desized cloth was
washed successively with hot and cold water prior to
scouring.
Scouring of the desized cotton cloth was performed
by the pad-steam technique. Application of sodium hy-
droxide was made by padding the fabric with 10%
NaOH solution containing 1.5±2% of an anionic deter-
gent in a two-bowl padding mangle, adjusting the
squeeze pressure to enable a wet pick-up of 100%. The
fabric was subsequently steamed in a laboratory steamer
at 100°C for 10 min. The scoured fabric was washed
with water, neutralized with dilute acetic acid, further
washed with water and ®nally dried in air.
2.3. Application of polymer ®nish on cotton
2.3.1. Acrylic ®nish
Pre-soaking of scoured cotton fabric with potassium
peroxodisulphate (K2 S2 O8 ) solution of known concen-
tration and subsequent application of aqueous AA
monomer formulation on the pre-soaked cotton fabric
were performed separately by padding technique [1±4] in
a laboratory two-bowl padding mangle. After two suc-
cessive dippings in the acrylic formulation, the pressure
between the squeezing rollers was adjusted to enable a
overall wet pick up of 100%. The monomer solution was
usually neutralized to pH 7 by the addition of required
dose of sodium carbonate. The aqueous monomer for-
mulation usually contained a known dose of NaH2 PO4
as the esteri®cation catalyst. The padded, squeezed
fabrics were allowed to stand at 30°C for di€erent time
periods (known as batching time) before they were
subjected to drying in an oven at 95°C for 5 min. The
dried fabrics were then oven-cured at 140°C for 5 min,
soap washed following ISO II [5], washed further with
water and air dried. They were then analysed for weight
gain, carboxyl and ester value and some textile-related
properties.
2.4. Dyeing
Desized, scoured cotton fabrics and those ®nished
with acrylic monomer system were dyed [5] using Bis-
mark Brown (CI Basic Brown 331) dye (4% on weight of
fabric) in a dyeing bath at 80°C for 1.5 h under stirring
condition; pH of the dyebath was adjusted at 4. After
completion of dyeing, the fabrics were washed with
distilled water and dried in air. E€ects of AA ®nish on
dyeability with a basic dye of the cotton fabric was then
evaluated.
2.4.1. Measurement of dyeability
In order to determine dyeability, K=S value of the
treated and untreated fabrics dyed with a basic dye were
examined in a Macbeth 2020 ‡ Reflectance Spectrome-
ter interfaced with a computer. The re¯ectance values
(R) of the dyed fabric at the wavelength of maxi-
mum absorption (kmax ˆ 540 nm) were converted to
the corresponding K=S value using the Kubelka±
Munk equation [5] i.e. …K=S† ˆ ‰…1 ÿ R†2 =2RŠ where K
is the absorption coecient and S is the scattering co-
ecient.
2.5. Determination of moisture regain and weight gain
after treatment
Moisture regain of the initial and treated cotton
fabrics was determined following a standard procedure
[6]. For the determination of weight gain upon ®nishing
treatments using AA, the ®nished fabric samples were
®rst soap washed and then extracted under re¯ux in a
water bath for 8±10 h successively using water and
methanol±water mixture in order to ensure removal of
traces of unreacted AA monomer along with polymeric
AA that remains unbound or ungrafted with the chain
molecules of cotton fabric sample. The extracted fabric
samples were then oven dried to a constant weight (W1 )
at 100°C. The weight gain (%) was then calculated on
the basis of initial dry weight of scoured cotton (W2 ),
using the following relationship: weight gain …%† ˆ
‰…W1 ÿ W2 †=W2 Š  100.
2.6. Tensile properties
Tenacity of some selected fabric samples were mea-
sured in a Zwick 1445 CRT Universal Tensile Testing
Machine, according to a method [7] prescribed by IS:
1969±1968. The results obtained were based on an av-
erage of 10 tests in the warp direction of each sample.
The test strip specimens were ravelled to a size of
50 mm  20 mm between the jaws of the machine and
 P. Ghosh, D. Das / European Polymer Journal 36 (2000) 2505±2511 2507

the tests were performed with a traverse speed of 100
mm/min at a pretension of 0.5 N.
2.7. Determination of acid value and ester value
Determinations of ±COOH group content and ester
value of selected cotton samples were made following
the methods described elsewhere [8,9]. The fabric sam-
ples were made (metallic) cation-free by dipping in dilute
HCl for 2 h and subsequently made HCl free by washing
with CO2 -free distilled water, prior to acid value and
ester value determination.
2.8. IR spectroscopy
IR spectra of unmodi®ed and selectively modi®ed
cotton samples were obtained following KBr pellet
technique as detailed elsewhere [10] using Shimadzu IR
440 spectrophotometer. The dried ®bre samples were
crushed to a size ®ner than 20 mesh before pelletizing
with KBr. The test KBr pellets contained about 1%
powdered ®bre.
2.9. Scanning electron microscopy
The surface morphology of cotton ®bres taken from
treated and untreated cotton fabrics was studied in a
Hitachi scanning electron microscope (Model S340).
The test ®bres were coated with gold±palladium alloy
using a sputter coater and observations were made at an
operating voltage of 18±20 kV.
3. Results and discussion
3.1. E€ect of variation of pH
Table 1 shows the e€ect of variation of pH of the AA
®nishing formulation on the properties of the ®nished
fabrics; relevant data clearly indicate that under neutral
condition (pH 7), optimum grafting and esteri®cation
leading to substantial weight gain are achieved with
nearly 80% retention of tenacity of the initial fabric
(data not shown). Slightly alkaline condition (pH 8,10),
also favours improved grafting of AA with an increasing
trend in ester group incorporation, however. Use of
acidic pH leads to notable weakening of the ®bre in the
fabric by acid hydrolysis. pH 7 apparently provides the
most optimum condition for the ®nishing process. No-
table incorporation of acid (±COOH) functional groups
on AA modi®cation of cotton fabric, using the dual
catalyst system as described above, expectedly leads to
much improved basic dye uptake …K=S† value, as shown
in Table 1. Moisture regain of unmodi®ed (bleached)
cotton (6.31%) gets substantially improved (to 9.5%) on
AA modi®cation at pH 7, using a batching time of 30
min at 30°C and on subsequent drying and curing under
prescribed condition.
3.2. Role of dual catalyst system for acrylic acid ®nishing
of cotton
It would be helpful, if we consider, at the outset, the
mechanism of modi®cation of cotton (Fig. 1) with AA

Table 1
Acrylic acid ®nishing of bleached cotton fabric: e€ect of variation of batching time and pHa
Finishing catalyst Batching Applica- Weight ±COOH Ester value Basic dye
K2 S2 O8 NaH2 PO4 time at tion pH gain (%) meq/100 g uptake
30°C (min) (K=S)
A. E€ect of variation of pH
+ + 30 5 5.77 14.87 29.03 5.77
+ + 30 7 7.57 23.05 23.68 21.46
+ + 30 8 7.82 26.03 20.61 23.84
+ + 30 10 7.86 28.14 11.94 24.17
B. E€ect of variation of batching time
+ + 0 7 5.68 15.53 16.68 16.21
+ + 15 7 6.57 19.01 19.21 20.03
+ + 30 7 7.57 23.05 23.68 21.46
+ + 45 7 7.63 23.84 23.77 22.53
+ + 60 7 7.84 24.62 19.01 23.75
) + 0 7 4.26 7.22 14.72 8.11
) + 30 7 5.83 7.31 16.13 11.47
+ ) 30 7 6.82 21.32 2.81 21.66
Only bleached cotton
± ± ± ± ± 1.26 0.46 0.87
a
Acrylic acid: 8%, K2 S2 O8 : 0.4%, NaH2 PO4 catalyst dovse: 8%, drying at 95°C, curing at 140°C.
2508 P. Ghosh, D. Das / European Polymer Journal 36 (2000) 2505±2511

Fig. 1. Reaction scheme showing modi®cation of cotton cellulose under the in¯uence of NaH2 PO4 as esteri®cation catalyst and
K2 S2 O8 as free-radical polymerization catalyst.

under the in¯uence of (i) NaH2 PO4 used as the esteri®-
cation catalyst and (ii) K2 S2 O8 used as the catalyst to
induce free-radical polymerization and graft copoly-
merization of AA on cotton. The sequence of reactions
shown in Fig. 1 would be expected to take place, ulti-
mately leading to notable weight gain and changes in the
chemical nature of cotton during the overall process.
NaH2 PO4 is known to be an ecient esteri®cation cat-
alyst [2] and reaction 1(a) producing AA ester of cotton
would be the direct consequence of its catalytic action.
However, the AA ester of cotton may then react with the
excess AA leading to thermal polymerization of the
monomeric acid as revealed by Eq. 1(b) (i) and to sub-
sequent crosslinking of cotton as shown by Eq. 1(b), (ii)
during the drying and curing step. Direct consequence of
esteri®cation under the in¯uence of NaH2 PO4 is, there-
fore, unlikely to enhance ±COOH group content of
cotton even though it would lead to enhancement in
the ester value of the product. However, uncatalysed
thermal polymerization of AA ultimately leading to
grafting of poly(acrylic acid) chains on the chain mole-
cules of cotton and ultimate crosslinking (Eq. 1(b)) po-
tentially occurs (in addition to peroxodisulphate
(S2 Oÿÿ
8 ) induced free-radical polymerization of AA,
(Eq. 2(a)±2(c)) if K2 S2 O8 is also included in the catalyst
system).
 P. Ghosh, D. Das / European Polymer Journal 36 (2000) 2505±2511
The thermal graft copolymerization and crosslinking
as shown by Eq. 1(b) ((i) and (ii)) would cause mea-
surable enhancements in the ±COOH content of the
product from which removal of the unbound (not
chemically bound to cotton) monomeric and polymeric
AA were ensured by solvent extractions.
On the other hand, direct in¯uence of the free-radical
catalyst, K2 S2 O8 over the batching time at room tem-
perature and at higher temperatures during drying and
curing would cause substantial enhancements in the
±COOH content of the modi®ed cotton, as a consequence
of graft copolymerization without enhancement in the
ester value. However, some purely thermal self-catalysed
esteri®cation involving ±OH groups in the chain mole-
cules of cotton and the ®nishing agent, AA during the
drying and curing process (95±140°C), even in the total
absence of the esteri®cation catalyst NaH2 PO4 cannot
be altogether precluded. Any enhancement in the ester
value of the AA modi®ed cotton in the absence of the
esteri®cation catalyst should thus be taken as a conse-
quence of this self (AA) catalysed thermal esteri®cation.
Under the in¯uence of the two catalysts taken to-
gether (NaH2 PO4 and K2 S2 O8 ) for the curing of cotton,
all the reactions shown and discussed above are likely to
take place simultaneously or successively leading to a
weight gain for the ®bre-fabric system (from which un-
reacted AA and the homopolymer of AA have been
removed by solvent (water) extraction) and enhance-
ment in its ±COOH group content (acid value) and ester
value. Moreover, additional reactions leading to further
esteri®cation and complex network formation (due to
limited establishment of ester linkages between the
carboxylic (±COOH) groups of a poly-carboxylic chain
bound to a particular cotton molecule and alcoholic
(±OH) groups of the same or other neighbouring cotton
cellulose molecules) may also take place.
Selected samples of AA ®nished cotton fabric were
further steeped in the cold in concentrated sulphuric
acid for 1 h, then diluted with ice cold water, ®ltered,
washed with cold water till the ®ltrate was acid-free,
dried and weighed. The weight of the residue was lower
by about 2±5% than the weight gain noted after the
®nishing treatment. Chemically, the residue resembled
poly(acrylic acid).
3.3. E€ect of variation of batching time
Relevant results are shown in Table 1. In each ex-
periment, AA dose level was maintained at 8% (w/w).
For batching at room temperature (30°C) for 0±60 min
under the dual catalyst system and subsequent drying by
heating at 95°C for 5 min, followed by curing at 140°C
for 5 min, there is a notable increase in the weight gain,
indicating that batching for an extended time distinctly
favours a higher incorporation of AA moieties on cotton
2509
due to prolonged scope for K2 S2 O8 -induced graft
copolymerization at room temperature (30°C).
The carboxylic content and the ester value tend
to increase as the batching time is increased from 0 to
60 min. There is little likelihood of establishment of ester
linkages at ambient temperatures over the di€erent pe-
riods of batching. Initial S2 Oÿÿ8 induced graft copoly-
merization or homopolymerization of AA, to increasing
extents over increasing batching time periods, at ambi-
ent temperature (30°C) and further polymerization of
free-AA and cotton bound AA moieties during the
subsequent drying period at 95°C cause an overall
change in environment and proximity of the hydroxyl
groups of cotton and carboxyl groups of the unbound or
cotton bound AA or poly(acrylic acid) moieties in a
manner that ®nally causes an enhanced degree of
NaH2 PO4 -catalysed esteri®cation and further chain po-
lymerization leading partly to crosslinking during curing
at 140°C. Data in Table 1 further show that non-use or
withdrawal of the esteri®cation catalyst, NaH2 PO4 is
prominently re¯ected in sharp lowering in the ester value
of the AA ®nished fabric.
The esteri®cation reaction that assumes more prom-
inence at the high processing temperature in the ®nal
stage (140°C) appears to be somewhat dependant on the
initial batching time. A higher batching time favours
improved transformation of the grafted-on AA/
poly(acrylic acid) units to ester moieties at the high
curing temperature (140°C) under the in¯uence of the
esteri®cation catalyst in the ®nal stages of processing.
Optimum batching time (30±45 min) also allows im-
proved di€usion/penetration of the ®nishing agent AA
within the interstices of the chain molecules of cotton.
This may well explain the trends of change in the acid
and ester values with change in batching time as shown
in Table 1. However, beyond an optimum period (30±45
min) of batching, the initial accumulation of poly(acrylic
acid) on cotton fabric by grafting and some degree of
crosslinking of cotton cellulose may become very high
indeed even prior to heating at the curing temperature
(140°C) and this may ultimately cause sti€ening of the
fabric for allowing more than the optimum batching
time, which is hence not recommended. In the absence of
NaH2 PO4 , the esteri®cation catalyst, simple peroxodi-
sulphate action expectedly leads to limited optimum
graft copolymerization and little esteri®cation over the
optimum batching period at 30°C; subsequent drying
and thermal curing ultimately produces a ®nished fabric
having much enhanced carboxyl content and poor ester
value.
Table 1 clearly shows that retention or improvements
in the functional group pattern, weight gain and basic
dye uptake value are optimal on pad-dry-curing of
bleached cotton with AA at pH 7 under the in¯uence
of the dual catalyst system, following a batching time of
30±45 min. Some textile related properties of cotton
2510 P. Ghosh, D. Das / European Polymer Journal 36 (2000) 2505±2511

fabric viz., tenacity, crease resistance, abrasion resis-
tance and ®bre/fabric ¯exibility also get optimally im-
proved for AA modi®cation under the prescribed
optimal condition (data not shown).
3.4. Scanning electron microscopy
In the cotton system, the surface morphology of the
bleached ®bre (micrograph (a) in Fig. 2) shows the
typical convolutions of the micro®brills with some dis-
tinct cracks in transverse or angular directions of the
®bre axis caused by the initial bleaching/scouring e€ect,
thereby causing some weakening of the ®bre. In the
micrograph for AA treated ®bre under the in¯uence of
only NaH2 PO4 as the esteri®cation catalyst (micrograph
(b) in Fig. 2), the said features are still visible though
somewhat masked or blurred, due to esteri®cation with
AA moieties and limited formation of ®lm of thermally
grafted-on poly(acrylic acid) on the surface. However,
the use of K2 S2 O8 as the polymerization catalyst either
alone (micrograph (c)) or in combination with the este-
ri®cation catalyst (micrograph (d)) results in substantial

Fig. 2. Scanning electron micrograph for (a) bleached cotton (´2200); and those for bleached cotton ®nished with AA in the presence
of (b) NaH2 PO4 only (´1800), (c) K2 S2 O8 only (´2000) and (d) mixture of NaH2 PO4 and K2 S2 O8 (´2100).
 P. Ghosh, D. Das / European Polymer Journal 36 (2000) 2505±2511
growth of cohesive ®lm of poly(acrylic acid), promi-
nently grafted/chemically anchored to the ®bre surface,
causing complete masking of the convolutions and sur-
face cracks; the masking e€ect appears to be more in-
tense due to higher incorporation and overgrowth of
AA/poly(acrylic acid) moieties, through graft copoly-
merization as well as due to extensive esteri®cation for
use of the dual catalyst system than when only the po-
lymerization catalyst is used.
3.5. IR analysis
The infrared spectra of unmodi®ed cotton ®bre
(spectrum (a)) and of the cotton ®bre di€erently modi-
®ed with AA treatment using only K2 S2 O8 as the free-
radical polymerization catalyst (spectrum (b)), using
only NaH2 PO4 as the esteri®cation catalyst (spectrum
(c)) and using both K2 S2 O8 and NaH2 PO4 catalysts to-
gether are shown in Fig. 3. A broad absorption band
over 3500±3000 cmÿ1 , characteristic of hydrogen bonded
O±H stretching vibration is common to all the four
spectra. Two notable absorption bands in the regions of
1560 and 1740 cmÿ1 appearing in di€erent intensities are
characteristic of carboxylate (anion) and ester stretching
vibrations, respectively. In the spectrum of unmodi®ed
cotton (cellulose), absorption bands over the 1500±2000
cmÿ1 are practically non-existent. AA ®nish of cotton in
the presence of K2 S2 O8 catalyst only, (spectrum (b) in
Fig. 3) results in appearance of a new weak absorption
band at 1566 cmÿ1 for the carboxylate anion. AA ®nish
of cotton in the presence of the esteri®cation catalyst
NaH2 PO4 only (spectrum (c) in Fig. 3), however, results
in intensi®cations of the absorption bands at 1790 and
1566 cmÿ1 for vinyl ester stretching (due to esteri®ca-
tion, reaction 1(a), Fig. 1) and carboxylate anion
stretching (due to reactions 1(b), Fig. 1) respectively,
Fig. 3. IR spectra of (a) unmodi®ed (bleached) cotton, and
of the bleached cotton modi®ed with AA in the presence of
(b) K2 S2 O8 , (c) NaH2 PO4 and (d) mixture of NaH2 PO4 and
K2 S2 O8 as catalysts.
2511
and a band at 1740 cmÿ1 corresponding to ester
stretching also appears in the said spectrum as expected.
However, AA ®nish on cotton under the in¯uence of the
dual catalyst (K2 S2 O8 ‡ NaH2 PO4 ) system (spectrum
(d) in Fig. 3) results in substantial weakening of the vinyl
ester stretching band at 1790 cmÿ1 (due to the signi®cant
disappearance of the vinyl group (incorporated on
esteri®cation) during ®nal stage polymerization induced
by heat and catalytic action of K2 S2 O8 , along with sharp
intensi®cation of the band at 1740 cmÿ1 (due to ester
stretching) with retention of the band corresponding to
1566 cmÿ1 for carboxylate (anion) stretching. The results
of the IR analysis are in tune with the mechanism pro-
posed.
4. Conclusions
The appropriate AA ®nish on cotton under neutral
conditions (pH 7) establishes a formaldehyde-free route
for achieving simultaneous core and surface modi®ca-
tion of cotton with high scope for incorporation of much
improved physical and mechanical properties for the
relevant ®bres, yarns and fabrics.
The major property advantages that can be derived
from AA ®nishes by following a pad-dry-cure technique
under the dual catalytic in¯uence of NaH2 PO4 and
K2 S2 O8 are substantial improvements in (1) weight gain
or tex value, (2) appearance, texture and ¯exibility, (3)
crease resistance, (4) moisture regain and (5) basic dye
uptake (K=S) value.
Mechanistic consideration, IR spectroscopy and
SEM analysis indicate that changes or improvements in
appearance, feel and other properties as mentioned
above are the direct consequences of di€erent degrees of
esteri®cation of cotton cellulose, grafting of ®lm forming
poly(acrylic acid) on the cellulosic substrate and notable
crosslinking of cellulosic chain molecules of cotton ®bre
through segments of the poly(acrylic acid) formed dur-
ing the pad-dry-cure process.
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