polymers
Article
Evaluation of Touch and Durability of Cotton Knit Fabrics
Treated with Reactive Urethane-Silicone Softener
Hang Sung Cho 1 , Hye Jun Yoon 1 , Bum Hoon Lee 2 , Jang Chang Woo 1 , Hyeong Yeol Choi 3 , Euijin Shim 1, * and
Ji Ho Youk 4, *
Citation: Cho, H.S.; Yoon, H.J.; Lee,
B.H.; Woo, J.C.; Choi, H.Y.; Shim, E.;
Youk, J.H. Evaluation of Touch and
Durability of Cotton Knit Fabrics
Treated with Reactive
Urethane-Silicone Softener. Polymers
2022, 14, 1873. https://doi.org/
10.3390/polym14091873
Academic Editor: Andrea Zille
Received: 8 April 2022
Accepted: 27 April 2022
Published: 3 May 2022
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4.0/).
Polymers 2022, 14, 1873. https://doi.org/10.3390/polym14091873
1 Advanced Textile R&D Department, Korea Institute of Industrial Technology (KITECH), Ansan-si 15588,
Korea; hscho@kitech.re.kr (H.S.C.); previa@kitech.re.kr (H.J.Y.); woocatcher@kitech.re.kr (J.C.W.)
2 Department of Textile Materials Engineering, Shinhan University, Dongducheon-si 11340, Korea;
bhlee@shinhan.ac.kr
3 Department of Fashion Design, Dong-A University, Busan 49315, Korea; spaachoi@dau.ac.kr
4 Department of Chemistry and Chemical Engineering, Education and Research Center for Smart Energy and
Materials, Inha University, Incheon 22212, Korea
* Correspondence: pelice35@kitech.re.kr (E.S.); youk@inha.ac.kr (J.H.Y.)
Abstract: A new reactive urethane–silicone softener was developed to provide a soft touch to cotton
knit fabrics with improved durability to washing and dimensional stability. The reactive urethane–
silicone softener consisted of an amino silicone softener and a blocked isocyanate, which can crosslink
and react with cellulose surfaces. The activated isocyanate from the blocked isocyanate reacted with
the amino silicone softener by heat treatment at 150 ◦ C for 30 min. The mechanical properties of
the cotton knit fabrics treated with the urethane–silicone softener were evaluated using a Kawabata
Evaluation System-Fabrics (KES-FB) system. The cotton knit fabrics treated with the urethane–silicone
softener showed excellent elasticity, flexibility and shear recovery as well as excellent recovery against
bending deformation, and soft and smooth surface characteristics with a small coefficient of friction
that were maintained even after washing 20 times.
Keywords: amino silicone softener; blocked isocyanate; KES-FB system; washing durability; dimen-
sional stability
1. Introduction
As living standards improve and textile product consumption becomes more advanced,
diversified, and differentiated, knitted cellulose products are considered high-quality
premium products, and consumer demand is increasing [1–4]. Knitted products made from
cellulose-based materials, such as cotton, rayon, and modal, are luxurious and flexible,
giving a comfortable feel. On the other hand, knitted fabrics lack dimensional stability
compared to woven fabrics [5–7]. Accordingly, continuous research is being conducted
on developing and processing elastic softeners for knitted products using cellulose to
improve the dimensional stability and commercialization of these cellulose knit products
as high-quality premium products [8–14].
Fabric softeners are used as additives and for in-home laundering in wet textile
processing to improve fabric handling. Conventional softeners do not chemically react
with cotton fibers, so there is a limit to improving the washing durability and dimensional
stability of cotton knitwear. Nevertheless, these softeners adhere to the fiber surface usually
through a weak electrical attraction without any chemical bonds, causing poor washing
durability. On the other hand, durable silicone-based fabric softeners render additional
performance properties to cotton fabric, such as improved wrinkle recovery and crease
resistance, and improved wear comfort with a smooth handle [15].
Several previous studies have used hydrated amino silicone oil to improve the reac-
tivity of cellulosic fibers with softeners. In these studies, the researchers emulsified the oil
https://www.mdpi.com/journal/polymers
Polymers 2022, 14, 1873 2 of 15

into small, stable nanoparticles by crosslinking, and reported improved washing durability,
dimensional stability, and yellowing [16,17]. Nevertheless, some emulsified particles may
remain on the fabric surface and can be partially concentrated, resulting in a white coating
in the form of aggregation rings [18,19].
In this study, to improve these drawbacks, a reactive urethane–silicone softener was
developed to impart a flexible feel to cellulose knitwear with enhanced washing durability
and dimensional stability. A urethane–silicone softener was prepared by mixing a blocked
isocyanate with an amino silicone softener to react with the fiber surface and the softener.
Because the reaction of the blocked isocyanate occurs only in the finishing process, the
disadvantage due to the rubber effect is improved when using a two-component treatment
agent in which a conventional silicone softener and water-soluble urethane are mixed. In
addition, to quantify the sensory characteristics of the flexible finish of the softening agent-
treated cellulose knitted fabric and evaluate the sensitivity, KES-FB (Kawabata Evaluation
System-Fabrics) was used to measure the objective mechanical properties of the cotton
knitted fabric processed with the urethane–silicone softener [20–22]. The urethane–silicone
softener-treated cotton fabrics exhibited excellent elasticity, flexibility, and shear recovery
after 20 washes, as well as excellent recovery against bending deformation, and soft and
smooth surface properties with a small coefficient of friction.

2. Materials and Methods

2.1. Materials
2,4,6-Trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene) isocyanate (HDI-trimer,
Vencorex, Incheon, Korea, 99.0%), 1,6-hexandiol (HD, Daejung chemical, Siheung-si, Korea,
99.5%), and poly(ethylene) glycol methyl ether (MPEG, IC chemical Korea, Yeosu, Korea,
98.0%) were used to synthesize the urethane prepolymer. A low-temperature curing type
3,5-dimethylpyrazole (DMP, Daejung chemical, 99%) was used to synthesize the blocked
isocyanate. The knit used in the flexible processing experiment is a 30-count single cotton
knitted fabric. After refining and bleaching, Turquoise blue dye (Suncion T/Blue HA,
Ohyoung, Seoul, Korea) was used at a concentration of 1.0% o.w.f at 80 ◦ C, and a dyeing
time of 60 min. It was dyed with a pilot.

2.2. Development of Urethane–Silicone Softener

2.2.1. Synthesis of Blocked Isocyanate
HDI-trimer, HD, and MPEG were added to a four-neck round bottom flask with a
reflux condenser attached at a molar ratio of 2/1/1 to synthesize the urethane prepolymer
through a reaction. DMP was added at a molar ratio of three to act as a blocking agent
to the prepared urethane prepolymer, causing a reaction that theoretically synthesized a
blocked isocyanate with the isocyanate (–NCO) group completely blocked off.

2.2.2. Urethane–Silicone Softener Manufacturing

Blocked isocyanate emulsions (0.5 wt.%) were first prepared by stirring the blocked
isocyanate in water at 2000 rpm for 30 min using a homogenizer. The blocked isocyanate
emulsion was blended into a commercial amino silicone softener (E-silky, Hyundae Hichem)
to manufacture the urethane–silicone softener. The commercial amino silicone softener was
prepared by the emulsion polymerization of hydrophilized amino-based silicone oil with a
0.9% amine content, consisting of dispersive particles with a particle size of 100 to 150 nm.

2.2.3. Determination of NCO Content

A 2 g sample was added to a 300 mL triangular flask, and 25 mL of an n-butylamine/toluene
solution at a molar concentration of one was added. The mixture was then shaken gently for
15 min. Subsequently, 150 mL of isopropyl alcohol and 0.5 mL of the indicator bromocresol
were added and mixed. Titration was performed with a 0.5 N hydrochloric acid solution.
The endpoint was the point where the blue or blue-violet color of the solution disappeared,
Polymers 2022, 14, 1873 3 of 15

and the yellow color lasted for more than 15 s. Finally, the –NCO content was determined
using the following equation [23–25]:

( B − S) × 42 × N × f
NCO(%) = × 100(%)
w × 1000
B: amount of 0.5 N hydrochloric acid solution by blank test (mL).
S: amount of 0.5 N hydrochloric acid solution used in the sample (mL).
42: molecular weight of NCO (g/mol).
N: normal concentration (N) of the hydrochloric acid solution used.
f : factor of 0.5 N hydrochloric acid solution.
w: mass of sample (g).

2.3. Softening Finishes

Pre-treated and dyed 30 s single cotton knit (32G/G, 130 g) was treated with a softener
diluted to 30 g/L, padded with a horizontal padder (DL-2005H, Daelim starlet, Siheung-si,
Korea) with a pickup ratio of 120% and padding pressure of one bar, and dried at 120 ◦ C
for 2 min to cure the fabric at 160 ◦ C for another 2 min.

2.4. Characterization
2.4.1. Particle Size Analysis
A laser scattering particle size distribution analyzer (LA950, Horiba, Kyoto, Japan)
was used to measure the average particle size of a softener emulsifier.

2.4.2. Fourier Transform Infrared (FTIR) Analysis

FTIR (Nicolet i5, Thermo Scientific, Waltham, MA, USA) spectroscopy was conducted
to confirm the progress of the reaction according to reaction temperature and time.

2.5. Evaluation of Mechanical Properties and KES-FB System Analysis of Cotton Knitwear Treated
with Urethane–Silicone Softener
The mechanical properties of cotton knitwear were compared before and after treat-
ment with an amino silicone softener (Sil-softer SB, Hyundae Hichem, Siheung-si, Korea)
as a reference and a urethane–silicone softener. The mechanical properties of the cotton
knit fabric processed with a softener were measured using the KES-FB system for tensile,
bending, surface, shear, and compression properties, weight, and thickness under the given
conditions listed in Table 1. All samples were cut to a 20 cm × 20 cm size. The measured
data were used by averaging the warp and weft wale results. In addition, the changes in
the mechanical properties of cotton knitwear after washes were also compared to confirm
the washing durability of the softener. The washing conditions were as follows: 66 g of
detergent (WOB, AATCC, Durham, NC, USA) was added to the softening agent-treated
cotton knitted fabric under normal general conditions, washed 20 times in a Canmore
washing machine, and dynamic properties were measured under the same conditions.

Table 1. Measurement parameter of the KES-FB system.

Properties Symbols Characteristic Values Unit Measuring Condition

LT Linearity - Max. Load: 50 gf/cm
Tensile properties WT Tensile energy gf·cm/cm2 Tensile speed: 0.1 mm/s
RT resilience % Measuring length: 2.5 cm
G shear stiffness gf/cm·degree
Shear properties Shear deformation: ±4◦
2HG Hysteresis at φ = 4◦ gf/cm
B Bending rigidity gf·cm2 /cm
Bending properties Bending curvature (K): ±2.5 cm
2HB Hysteresis gf·cm/cm
T0 Thickness of fabric mm Max. Load: 10 gf/cm2
Compression properties Compression speed: 50 mm/s
WC Compressional energy gf·cm/cm2 Compression area: 2 cm2
MIU Coefficient of friction - Friction static load: 50 g
Surface properties
SMD Geometrical roughness micron Roughness static load: 5 g
 T0 Thickness of fabric mm Max. Load: 10 gf/cm2
Compression properties Compression speed: 50 mm/sec
WC Compressional energy gf·cm/cm2
Compression area: 2 cm2
MIU Coefficient of friction - Friction static load: 50 g
Surface properties
Polymers 2022, 14, 1873 SMD Geometrical roughness micron Roughness static load: 5 g 4 of 15

3. Results and Discussion

3. Results
3.1. andofDiscussion
Synthesis Blocked Isocyanate
3.1. Synthesis of Blocked
A blocked isocyanate Isocyanate
was synthesized to develop a reactive urethane–silicone sof-
tenerAand
blocked
improveisocyanate was
the feel synthesized
and durabilitytoofdevelop
cotton afabric.
reactive
Forurethane–silicone
the synthesis of softener
blocked
and improveHDI-trimer,
isocyanate, the feel and durability
HD, and MPEGof cotton fabric.
were For the
reacted at synthesis of blocked
a molar ratio isocyanate,
of 2/1/1 to poly-
HDI-trimer, HD, and
merize urethane MPEG were
prepolymer, as reacted
shown in at aFigure
molar1.ratio
Theofnumber
2/1/1 toofpolymerize
moles of theurethane
–NCO
prepolymer, as shown in Figure 1. The
group was more significant than the number of number of moles of the –NCO group was
the added hydroxyl group more
significant
(-OH) of HD thanand theMPEG.
number of moles
Hence, of the group
the –NCO added that
hydroxyl
did not group (-OH)a of
undergo HD and
reaction re-
MPEG.
mainedHence,
in the the –NCO prepolymer.
urethane group that did not undergo athe
Subsequently, reaction
DMP remained in the urethane
blocker reacted with the
prepolymer.
remaining –NCO Subsequently, the DMP
group, resulting in ablocker
blocked reacted with the
isocyanate, remaining
where the –NCO –NCO group,
group was
resulting in a
sealed [26–28]. blocked isocyanate, where the –NCO group was sealed [26–28].

Figure 1. Synthesis
Figure1. Synthesis scheme
scheme of
of urethane
urethane prepolymer
prepolymer and
and blocking
blocking of
of the
the residual
residual isocyanate
isocyanate groups
groups
usingaablocking
using blockingagent.
agent.

Figure 2 presents a schematic diagram of the sealing reaction that deactivates the
residual –NCO group and reactivates the –NCO group during heat treatment. The residual
–NCO group was sealed using blockers for stability and storage while processing the
obtained urethane prepolymer. The reactivated –NCO group can react with the –OH
group to form urethane bonds or a –NH2 group to form urea bonds [26,29]. Figure 3
presents a schematic diagram of the reaction between the cellulose fabric and the developed
softener. Figure 4 schematically shows the particle size and reaction of the conventional
softener and the reactive urethane–silicone softener on the fabric surface. Particles that
are 1/20 times smaller than conventional particles can increase surface area and surface
reactivity. Further, since the particle size of the softener is small, there is an advantage
in that the permeability of the fabric is improved and the durability is improved [8]. In
addition, it has morphological stability due to the crosslinking reaction with urethane.

Polymers 2022, 14, 1873
oped softener. Figure 4 schematically shows the particle size and reaction of the conven-
oped softener. Figure 4 schematically shows the particle size and reaction of the conven-
tional softener and the reactive urethane–silicone softener on the fabric surface. Particles
tional softener and the reactive urethane–silicone softener on the fabric surface. Particles
that are 1/20 times smaller than conventional particles can increase surface area and sur-
that are 1/20 times smaller than conventional particles can increase surface area and sur-
face reactivity. Further, since the particle size of the softener is small, there is an ad-
face reactivity. Further, since the particle size of the softener is small, there is an ad-
vantage in that the permeability of the fabric is improved and the durability is improved
vantage in that the permeability of the fabric is improved and the durability is improved
5 of 15
[8]. In addition, it has morphological stability due to the crosslinking reaction with ure-
[8]. In addition, it has morphological stability due to the crosslinking reaction with ure-
thane.
thane.

Figure 2.
Figure 2. Blocking
Blocking and
and reactivation
reactivation reaction
reaction mechanism
mechanism of
of the
the isocyanate
isocyanategroups.
groups.
Figure 2. Blocking and reactivation reaction mechanism of the isocyanate groups.

Polymers 2022, 14, x FOR PEER REVIEW 6 of 16

Figure 3. Crosslinking chemical mechanism of cellulosic fabrics and softeners.
Figure3.3.Crosslinking
Figure Crosslinkingchemical
chemicalmechanism
mechanismof
ofcellulosic
cellulosicfabrics
fabricsand
andsofteners.
softeners.

Figure
Figure4.4.Schematic
Schematic of of
conventional softener
conventional andand
softener reactive urethane-silicone
reactive softeners.
urethane-silicone (a) conven-
softeners. (a) conventional
tional softener; (b) reactive urethane-silicone softener.
softener; (b) reactive urethane-silicone softener.

Figure
Figure5 5shows
shows the change
the changein in
thethe
–NCO
–NCOgroup
groupcontent according
content to the
according to reaction
the reaction time
time determined by titration of the urethane prepolymer. The change in
determined by titration of the urethane prepolymer. The change in the contentthe content of– of–NCO
NCO groups according to the reaction time was similar at 30 and 60 °C, but the content
groups according to the reaction time was similar at 30 and 60 ◦ C, but the content of
of –NCO groups according to reaction time at 90 °C◦ decreased significantly. Therefore,
–NCO groups according to reaction time at 90 C decreased significantly. Therefore, the
the reaction temperature of the HDI-trimer, HD, and MPEG for the synthesis of the ure-
reaction
thane temperature
prepolymer of the HDI-trimer,
was determined to be 90 °C,HD,
withand MPEGtime
a reaction for the
of 90synthesis
min [30]. of the urethane
prepolymer was determined to be 90 ◦ C, with a reaction time of 90 min [30].
20

15
 Figure 5 shows the change in the –NCO group content according to the reaction
time determined by titration of the urethane prepolymer. The change in the content of–
NCO groups according to the reaction time was similar at 30 and 60 °C, but the content
of –NCO groups according to reaction time at 90 °C decreased significantly. Therefore,
Polymers 2022, 14, 1873 6 of 15
the reaction temperature of the HDI-trimer, HD, and MPEG for the synthesis of the ure-
thane prepolymer was determined to be 90 °C, with a reaction time of 90 min [30].

20

15

-NCO (%)

10

5
30 °C
60 °C
90 °C
0
0 30 60 90 120
Reaction time (min)
Figure
Figure5.5.Changes
Changesininthe
the–NCO
–NCOgroup
groupcontent
contentwith
withthe
thereaction
reactiontime
timeand
andtemperature.
temperature.

Figure66shows
Figure showschanges
changesininthe the–NCO
–NCOcontent
contentaccording
accordingtotothethereaction
reactiontime
timeandand
temperature of a urethane prepolymer and DMP. This
temperature of a urethane prepolymer and DMP. This study used DMP, astudy used DMP, a low-temperature
curing type, withcuring
low-temperature an activation
type, withtemperature
an activation to 120 ◦ C asofa 110
of 110temperature blocking
to 120agent.
°C asThea
blocking agent. The urethane prepolymer and DMP contained –NCO groups that after
urethane prepolymer and DMP contained –NCO groups that did not react with DMP did
90 min
not
Polymers 2022, 14, x FOR PEER REVIEW reactreaction
with DMP at 4090◦ C,
timeafter minbutreaction
very little
time–NCOat 40 remained
°C, but veryafter 60 min
little –NCO reaction time
remained
7 of 16
◦
at 7060C. Therefore,
after min reactionthe basic
time at 70reaction conditions
°C. Therefore, thefor urethane
basic prepolymer
reaction conditionsand forDMP were
urethane
determinedand
prepolymer to beDMPa reaction temperatureto
were determined ofbe70 a◦ C with a reaction
reaction time of
temperature of 70
60 °C
min.with a re-
action time of 60 min.
25
40 °C
70 °C
20
- NCO (%)

15

10

0 30 60 90
Reaction time (min)

Changesinin–NCO
Figure6.6.Changes
Figure –NCOgroup
groupcontent
contentwith
withthe
thereaction
reactionof
ofthe
theurethane
urethaneprepolymer
prepolymerand
andDMP.
DMP.

3.2. Characterization of Urethane–Silicone Softener

3.2. Characterization of Urethane–Silicone Softener
A blocked isocyanate emulsion (0.5 wt.%) was prepared by first stirring the blocked
A blocked
isocyanate isocyanate
in water at 2000 emulsion
rpm for 30(0.5
minwt. %)a was
using prepared The
homogenizer. by first stirring the
urethane–silicone
blocked isocyanate in water at 2000 rpm for 30 min using a homogenizer.
softener was prepared by blending 0.5% by weight of a blocked isocyanate emulsionThe urethane–
with
silicone softener was prepared by blending 0.5% by weight of a blocked isocyanate
a commercially available amino silicone softener (E-silky, Hyundai Hichem, Siheung-si,
emulsion
Korea). Thewith a commercially
particle availableblocked
size of the prepared amino isocyanate
silicone softener
emulsion(E-silky, Hyundai
was 0.059 nm on
Hichem, Siheung-si, Korea).
average, as shown in Table 2. The particle size of the prepared blocked isocyanate emul-
sion was 0.059 nm on average, as shown in Table 2.

Table 2. Particle size of the blocked isocyanate emulsion.

Sample Particle Size (um)

Blocked isocyanate emulsion 0.059213
Polymers 2022, 14, 1873 7 of 15

Table 2. Particle size of the blocked isocyanate emulsion.

Sample Particle Size (um)

Blocked isocyanate emulsion 0.059213

Figure 7 presents the FTIR spectra of a mixture of the amino silicone softener and
the blocked isocyanate before and after drying at 150 ◦ C for 30 min. After heat treatment,
multiple absorption bands were observed in the C=O regions (1700 cm−1 ). The changes
were related to hydrogen bonding of the urethane or urea groups [31]. This is the peak
that shows that the crosslinking reaction between blocked isocyanate and amino silicone
has occurred. As suggested in Figure 2, the heat treatment induced a reaction between the
emulsified blocked isocyanate and the amino silicone softener. The hydroxyl groups (–OH
groups) on the surface of the cotton fabric can react with blocked isocyanates to improve
the wash durability and dimensional stability of cotton knitwear. The –NCO group of the
isocyanate is regenerated after unblocking, and a urethane bond is formed with the8 –OH
Polymers 2022, 14, x FOR PEER REVIEW of 16
group of the cellulose fabric. This chemical bond provides a strong covalent bond between
the fabric and the softener. In this way, the isocyanate acts as a coupling agent for fabric
surface modification [32,33].

Figure 7.
Figure FTIR spectra
7. FTIR spectra of
of aa mixture
mixture of
of amino
amino silicone
silicone softener
softener and
and blocked
blocked isocyanate
isocyanate before
before (blue
(blue
◦
color) and after (red color) drying at 150 °CC for 30 min.
color)

The peaksofobserved
3.3. Evaluation Mechanicalin Properties
both spectraand regardless
KES-FB Systemof heat treatment are as follows: The
Analysis
peak at 2960 cm−1 is attributed to the C–H stretch absorption of CH3 groups, and the
3.3.1. Tensile Properties of Cotton Knitwear after Softener Treatment
810 cm−1 band is due to Si–C [34,35]. Furthermore, the peak due to Si–O–Si asymmet-
Figure 8 presents
ric stretching, the resultappears
which generally of the tensile
in theproperties
range of 950of cotton
cm−1 to knitwear
1200 cm treated
−1 , waswith
ob-
softeners. The linearity
− 1 (LT), tensile energy per unit area (WT), and
served at 1075 cm , and Si–CH3 bonding due to CH symmetric strain was observed at resilience (RT) were
1250 cm−1 as
measured tensile properties. The smaller the LT value, the easier the tensile defor-
[36].
mation of fabric. Moreover, the greater the elasticity of the fabric, the greater the LT val-
3.3.[37].
ue Evaluation of Mechanical
The average Properties
LT values for theand
waleKES-FB Systemdirection
and course Analysis of the untreated cotton
3.3.1. Tensile
knitwear wereProperties
similar toofthe
Cotton
valuesKnitwear
of cottonafter Softener
knitwear Treatment
treated with the Sil-softer SB and
urethane–silicone
Figure 8 presents the result of the tensile properties of cotton excellent
softener (Figure 8a). This is probably due to the knitweartensile
treatedprop-
with
erties that knits have inherently [38]. The LT values of the three-cotton
softeners. The linearity (LT), tensile energy per unit area (WT), and resilience (RT) knitwear showed
were
similar
measured values even properties.
as tensile after 20 washes, indicating
The smaller the LTexcellent
value, thedurability
easier the(Figure
tensile 8a). In other
deformation
words, the chemical reaction between urethane–silicone and the fiber surface helped
improve the overall tensile properties.
WT is the tensile energy during tensile deformation that occurs when weight is ap-
plied to the fabric, and the value of WT increases with increasing length. The WT value
was the largest in cotton knitwear treated with the urethane–silicone softener (Figure
Polymers 2022, 14, 1873 8 of 15

of fabric. Moreover, the greater the elasticity of the fabric, the greater the LT value [37]. The
average LT values for the wale and course direction of the untreated cotton knitwear were
similar to the values of cotton knitwear treated with the Sil-softer SB and urethane–silicone
softener (Figure 8a). This is probably due to the excellent tensile properties that knits have
inherently [38]. The LT values of the three-cotton knitwear showed similar values even
after 20 washes, indicating excellent durability (Figure 8a). In other words, the chemical
reaction between urethane–silicone and the fiber surface helped9 improve
Polymers 2022, 14, x FOR PEER REVIEW of 16 the overall tensile
properties.

1.0 (a) Unwashed

20 times washing

0.8
Linearity

0.6

0.4

0.2

0.0
Untreated Silicone Urethane-silicone

4.0
(b) Unwashed
3.5 20 times washing
Tensile energy (gf·cm/cm2)

3.0

2.5

2.0

1.5

1.0

0.5

0.0
Untreated Silicone Urethane-silicone

60 (c) Unwashed
20 times washing
50
Resilience (%)

40

30

20

10

0
Untreated Silicone Urethane-silicone
.
Figure 8. Tensile properties of the cotton knit fabric untreated and treated with softeners. (a) Linearity;
(b) tensile energy; (c) resilience.

WT is the tensile energy during tensile deformation that occurs when weight is applied
to the fabric, and the value of WT increases with increasing length. The WT value was
the largest in cotton knitwear treated with the urethane–silicone softener (Figure 8b),
Polymers 2022,
Polymers 14,14,
2022, 1873
x FOR PEER REVIEW 10 of 16 9 of 15

Figure 8. Tensile properties of the cotton knit fabric untreated and treated with softeners. (a) Line-
indicating
arity; that when
(b) tensile energy; tensile energy is applied per unit area of WT, it is
(c) resilience. possible to show
that the elasticity is good because it has the greatest value in the cotton knit treated with
3.3.2. Shear Properties ofsoftener.
urethane–silicone Cotton Knitwear after Softener Treatment
Figure 9 presents the
RT represents recoveryshear properties
from of cottonstrain.
tensile knitwearThe
treated with the
higher a softener.
RT value, the better the
The G value, which represents the shear rigidity, is affected by the contact pressure and
recovery [37]. Figure 8c shows that the cotton knitted fabric treated
friction between the yarns that make up the fabric. A lower G value means the fabric is
with the urethane–
silicone softener recovers best after applying tensile strength. The
deformed more easily in the diagonal direction. If deformation occurs easily in the di- average RT value of the
threedirection,
agonal cotton knitted
the personfabrics decreased
wearing the fabricsignificantly
can feel moreafter washing
comfortable 20the
with times. After washing,
movement.
some of Cotton knitwearhas
the softener treated with thebut
no choice urethane–silicone
to fall off duesoftener had the smallest
to physical force [39–42]. Comparing
G value (Figure 9a), meaning that it was most prone to shear deformation. This tendency
the resilience after 20 washes, the resilience value was lower than that of untreated when
did not change even after washing 20 times.
using silicone
A smaller 2HGsoftener, but it was
value representing thethe highest
history at 35%
of shear when
rigidity usingbetter
indicated urethane–silicone
re- softener.
This value
silience is moretoflexible
(recoverability) than the untreated,
shear deformation unwashed
[37]. A comparison of thesample.
2HG values in
Figure 9b showed that the cotton knitwear treated with urethane–silicone softener
3.3.2. the
showed Shear
bestProperties of Cottonfor
recovery performance Knitwear after Softener
shear deformation becauseTreatment
of the smallest
2HG value. Overall, cotton knitwear treated with urethane–silicone softener showed ex-
Figure 9 presents the shear properties of cotton knitwear treated with a softener. The
cellent flexibility and resilience against shear stress. Therefore, applying softener ap-
G value,
peared which
to have represents
brought about a the shearinrigidity,
reduction is affected
shear rigidity byshear
(G) and the contact pressure and friction
hysteresis
between
(2HG) values,the yarnstothat
leading make up the
the improvement of fabric. A lower
fabric handle and G value means
formability the fabric is deformed
properties
[43].
more easily in the diagonal direction. If deformation occurs easily in the diagonal direction,
The increased 2HG value indicates that the washed fabric has poorer recovery than
the person wearing the fabric can feel more comfortable with the movement. Cotton
the untreated fabric [44]. The increase in the 2HG value after washing is believed to
knitwear
hinder recoverytreated
when with the urethane–silicone
shear deformation is applied duesoftener had the
to the shrinkage of smallest
the sampleG value (Figure 9a),
meaning that it was most prone to shear deformation. This tendency
by washing [45,46]. Thus, the chemical reaction between urethane–silicone and the fiber did not change even
surface helps to improve
after washing 20 times. the overall shear properties, such as the tensile properties.

1.2
(a) Unwashed
20 times washing
Shear stiffness (gf/cm·degree)

1.0

0.8

0.6

0.4

Polymers 2022, 14, x FOR PEER REVIEW 0.2 11 of 16

0.0
Untreated Silicone Urethane-silicone
2.0
(b) Unwashed
20 times washing

1.5
Hystresis (gf/cm)

1.0

0.5

0.0
Untreated Silicone Urethane-silicone

Figure
Figure 9. Shear
9. Shear properties
properties of the
of the cotton knitcotton knit fabric
fabric untreated untreated
and treated and treated
with softeners. with
(a) Shear softeners. (a) Shear
stiffness; (b) hysteresis.
stiffness; (b) hysteresis.
3.3.3. Bending Properties
A smaller 2HG of Cotton
value Knitwear after Softener
representing Treatment
the history of shear rigidity indicated better re-
Figure 10
silience shows the bending
(recoverability) toproperties of cotton knitwear
shear deformation [37].treated with a softener.
A comparison of the 2HG values in
The B value represents the bending rigidity, which demonstrates the stiffness of the fab-
Figure 9b showed that the cotton knitwear treated with urethane–silicone softener showed
ric. The larger the value, the stiffer the fabric, and the smaller the value, the more flexible
thethe bestArecovery
fabric. comparisonperformance
of the B values for shearcotton
revealed deformation because
knitwear treated withof
thethe
ure-smallest 2HG value.
thane–silicone softener to have the smallest value (Figure 10a), demonstrating its excel-
lent flexibility. This tendency did not change, even after washing 20 times. In addition, a
smaller 2HB value indicates a history of bending deformation, which demonstrates ex-
cellent bending resilience. As a result of comparing the 2HB value, the cotton knitted
fabric with the added urethane–silicone softener showed the smallest value for bending
 Polymers 2022, 14, x FOR PEER REVIEW 11 of 16

2.0
Polymers 2022, 14, 1873
(b) Unwashed 10 of 15
20 times washing

1.5

Hystresis (gf/cm)
Overall, cotton knitwear treated with urethane–silicone softener showed excellent flexibility
and resilience against shear stress. Therefore, applying softener appeared to have brought
1.0
about a reduction in shear rigidity (G) and shear hysteresis (2HG) values, leading to the
improvement of fabric handle and formability properties [43].
The increased 2HG value indicates that the washed fabric has poorer recovery than
0.5
the untreated fabric [44]. The increase in the 2HG value after washing is believed to
hinder recovery when shear deformation is applied due to the shrinkage of the sample
by washing
0.0
[45,46]. Thus, the chemical reaction between urethane–silicone and the fiber
Untreated
surface helps to improveSilicone Urethane-silicone
the overall shear properties, such as the tensile properties.
Figure 9. Shear properties of the cotton knit fabric untreated and treated with softeners. (a) Shear
3.3.3. Bending Properties of Cotton Knitwear after Softener Treatment
stiffness; (b) hysteresis.
Figure 10 shows the bending properties of cotton knitwear treated with a softener. The
3.3.3. Bending
B value Propertiesthe
represents of Cotton Knitwear
bending after which
rigidity, Softenerdemonstrates
Treatment the stiffness of the fabric. The
larger the value, the stiffer the fabric, and the smaller the value,athe
Figure 10 shows the bending properties of cotton knitwear treated with softener.
more flexible the fabric.
The B value represents the bending rigidity, which demonstrates the stiffness of the fab-
A comparison of the B values revealed cotton knitwear treated
ric. The larger the value, the stiffer the fabric, and the smaller the value, the more flexible
with the urethane–silicone
softener
the fabric. Ato have theof smallest
comparison the B values value (Figure
revealed cotton 10a),
knitweardemonstrating
treated with the its ure-excellent flexibility.
This tendency
thane–silicone didtonot
softener havechange, even
the smallest after
value washing
(Figure 20 times. Initsaddition,
10a), demonstrating excel- a smaller 2HB
lent flexibility.
value This tendency
indicates a history didof not change, even
bending after washing
deformation, 20 times.
which In addition, a excellent bending
demonstrates
smaller 2HB value indicates a history of bending deformation, which demonstrates ex-
resilience. As a result of comparing the 2HB value, the cotton knitted fabric with the added
cellent bending resilience. As a result of comparing the 2HB value, the cotton knitted
urethane–silicone
fabric softener showed
with the added urethane–silicone the smallest
softener showed the value forvalue
smallest bending deformation, which was
for bending
maintained
deformation, even
which was after washing
maintained 20after
even times, demonstrating
washing that it had
20 times, demonstrating thatthe
it greatest restoring
had the greatest
force (Figurerestoring
10b). force (Figure 10b). Inthe
In conclusion, conclusion, the urethane–silicone
urethane–silicone softener soften-
acts as a reinforcing
ermaterial
acts as a reinforcing material
for the knitted for thebecause
fabric knitted fabric
of itsbecause of its and
flexibility flexibility and the
the elasticity of urethane and
elasticity of urethane and silicone due to the chemical bonding of the fabric surface
silicone
[15,43,47,48].
due to the chemical bonding of the fabric surface [15,43,47,48].

(a) Unwashed
0.04 20 times washing
Bending rigidity (gf·cm2/cm)

0.03

0.02

0.01

Polymers 2022, 14, x FOR PEER REVIEW 12 of 16

0.00
Untreated Silicone Urethane-silicone

(b) Unwashed
0.04 20 times washing
Hysteresis (gf·cm/cm)

0.03

0.02

0.01

0.00
Untreated Silicone Urethane-silicone

Figure 10. Bending properties of the cotton knit fabric untreated and treated with softeners.
Figure 10. Bending properties of the cotton knit fabric untreated and treated with softeners. (a)
(a) Bending
Bending rigidity;rigidity; (b) hysteresis.
(b) hysteresis.

3.3.4. Compression Properties of Cotton Knitwear after Softener Treatment

The compression properties are factors that can evaluate the volume properties of
the fabric. Figure 11 shows the results of the compression properties of cotton knitwear
treated with a softener. The T0 represents the thickness of the fabric, and WC represents
the compression energy of the fabric.
 Untreated Silicone Urethane-silicone

Figure 10. Bending properties of the cotton knit fabric untreated and treated with softeners. (a)
Bending rigidity; (b) hysteresis.

3.3.4. Compression Properties of Cotton Knitwear after Softener Treatment

Polymers 2022, 14, 1873 The compression properties are factors that can evaluate the volume properties of 11 of 15
the fabric. Figure 11 shows the results of the compression properties of cotton knitwear
treated with a softener. The T0 represents the thickness of the fabric, and WC represents
the compression energy of the fabric.
3.3.4. Compression
A comparison Properties
of the fabric of revealed
thickness Cottonthe Knitwear after Softener
urethane–silicone Treatment
softener-treated
cotton knitted fabric to be thicker (Figure 11a). The larger the WC value,
The compression properties are factors that can evaluate the volume the bulkier the properties of
fabric is. The WC value of cotton knitwear treated with the urethane–silicone softener
the fabric. Figure 11 shows the results of the compression properties
was the largest (Figure 11b). The increase in physical thickness through silicone–
of cotton knitwear
treatedaffects
urethane withthea softener.
compression The T0 represents
properties. the thickness
This suggests of thereaction
that the chemical fabric,ofand WC represents
the
the compression
softener on the fiberenergy
surface of
may the fabric.
help improve the compression properties [47].

1.6

1.4
(a) Unwashed
20 times washing

1.2
Thickness (mm)

1.0

0.8

0.6

0.4

Polymers 2022, 14, x FOR PEER REVIEW 0.2 13 of 16

0.0
Untreated Silicone Urethane-silicone

0.06
(b) Unwashed
Compressional energy (gf·cm/cm2)

20 times washing
0.05

0.04

0.03

0.02

0.01

0.00
Untreated Silicone Urethane-silicone

Figure
Figure 11. Compression
11. Compression propertiesproperties
of the cottonofknit
thefabric
cotton knit fabric
untreated untreated
and treated and treated
with softeners. with softeners.
(a) (a) Thickness;
Thickness; (b) compressional
(b) compressional energy. energy.

3.3.5. Surface Properties of of

A comparison Cotton
the Knitwear after Softener
fabric thickness Treatment
revealed the urethane–silicone softener-treated
Figureknitted
cotton 12 showsfabric
the coefficient of friction
to be thicker (MIU)11a).
(Figure measurements
The largerand the
geometrical
WC value, the bulkier the
roughness (SMD) measurements of the surface properties of the cotton knitwear treated
fabric is. The WC value of cotton knitwear treated with the urethane–silicone softener
with a softener. The first parameter, MIU, is correlated with the soft and smooth feeling
wasthe
when thesurface
largest (Figure
of an object 11b). The increase
is touched; in physical
a smaller MIU thickness
value indicates through
a softer and silicone–urethane
affectsfabric.
smoother the compression
The SMD indicatesproperties.
the surfaceThis suggests
physical thata the
evenness; chemical
higher reaction of the softener
value repre-
sents an uneven surface [49].
on the fiber surface may help improve the compression properties [47].
The MIU of the cotton knitwear treated with urethane–silicone softener was the
smallest,
3.3.5. showing
Surfacethe soft and smooth
Properties surface
of Cotton propertiesafter
Knitwear (Figure 12a). This
Softener is because
Treatment
the urethane–silicone softener has a small particle size on the nanoscale, and thus pene-
Figure
trates better 12inner
into the shows the of
structure coefficient of friction (MIU) measurements and geometrical
the fabric [15].
roughness (SMD) measurements
The SMD indicates of the
surface irregularities, andsurface properties
urethane–silicone of the cotton knitwear treated
softener-treated
cotton
withknitwear showed
a softener. the first
The highest value (Figure
parameter, 12b).is
MIU, This is the result
correlated of a the
with change in and smooth feeling
soft
the geometry of the sample due to fabric shrinkage and the changes in thickness [50]. In
when the surface of an object is touched; a smaller MIU value indicates a softer and
addition, after washing 20 times, all three samples showed increased SMD values. It is
smoother
thought fabric.
that the Thebond
chemical SMD indicates
of the the surface
urethane–silicone physical
softener evenness;
increases a higher value represents
the durability
an uneven
rather surface bond
than the physical [49].of a general softener, indicating strength in the smooth-
ness of the surface [15].
Polymers 14, 14,
2022,2022,
Polymers 1873
x FOR PEER REVIEW 14 of 16 12 of 15

0.35
(a) Unwashed
0.30 20 times washing

Coefficient of friction
0.25

0.20

0.15

0.10

0.05

0.00
Untreated Silicone Urethane-silicone

6
(b) Unwashed
20 times washing
5
Geometrical roughness

0
Untreated Silicone Urethane-silicone

Figure
Figure 12. Surface
12. Surface propertiesproperties
of the cotton of
knitthe cotton
fabric knit
untreated andfabric
treated untreated and
with softeners. treated
(a) Co- with softeners.
(a) Coefficient
efficient of friction; of
(b) friction;
geometrical(b) geometrical roughness.
roughness.

4. Conclusions
The MIU of the cotton knitwear treated with urethane–silicone softener was the
This study
smallest, examined
showing thethesoft
effect
andof using
smooth a reactive
surface softener, and the(Figure
properties washing12a).
dura- This is because the
bility of the cellulose-based cotton knitted fabric. For this purpose, a nanoscale softener
urethane–silicone softener has a small particle size on the nanoscale, and thus penetrates
was prepared by synthesizing a reactive urethane–silicone softener. The optimal reaction
better into
conditions for the
the inner
urethanestructure
prepolymer of the fabric [15].
for blocked isocyanate synthesis were deter-
mined to The
be SMD
90 minindicates surface
at 90° C through irregularities,
content analysis of and
–NCO urethane–silicone softener-treated cotton
groups. Residual –NCO
blocking
knitwear of the urethanethe
showed prepolymer
highestwas performed
value using
(Figure low-temperature
12b). This is the DMP at 70of a change in the
result
°C for 60 min. The processability of the prepared urethane–silicone softener was evalu-
geometry of the sample due to fabric shrinkage and the changes in thickness [50]. In
ated using the KES-FB system after application to a cotton knit fabric. The chemical reac-
addition,
tion between after washing
the surface of the 20 times,
cotton fabricall
andthree samples showed
the silicone–urethane increased
softener was ef- SMD values. It is
thought
fective that thedimensional
in imparting chemical bond stabilityofinthe urethane–silicone
all physical softener
properties. The increases the durability
cotton knitted
fabric
rathertreated
thanwith the urethane–silicone
the physical bond of a softener
generalexhibited
softener, soft and smooth
indicating surface in the smoothness
strength
properties due to the
of the surface elasticity, flexibility, and restoring force against shear strength, as
[15].
well as the restoring force against bending deformation and low coefficient of friction.
These properties were maintained even after 20 washes. As a result, the prepared na-
4. Conclusions
noscale reactive softener showed excellent performance in cotton knitwear. Therefore, it
This study examined the effect of using a reactive softener, and the washing durability
of the cellulose-based cotton knitted fabric. For this purpose, a nanoscale softener was
prepared by synthesizing a reactive urethane–silicone softener. The optimal reaction
conditions for the urethane prepolymer for blocked isocyanate synthesis were determined
to be 90 min at 90◦ C through content analysis of –NCO groups. Residual –NCO blocking of
the urethane prepolymer was performed using low-temperature DMP at 70 ◦ C for 60 min.
The processability of the prepared urethane–silicone softener was evaluated using the
KES-FB system after application to a cotton knit fabric. The chemical reaction between the
surface of the cotton fabric and the silicone–urethane softener was effective in imparting
dimensional stability in all physical properties. The cotton knitted fabric treated with the
urethane–silicone softener exhibited soft and smooth surface properties due to the elasticity,
Polymers 2022, 14, 1873 13 of 15

flexibility, and restoring force against shear strength, as well as the restoring force against
bending deformation and low coefficient of friction. These properties were maintained
even after 20 washes. As a result, the prepared nanoscale reactive softener showed excellent
performance in cotton knitwear. Therefore, it is expected to provide excellent performance
and durability when applied to various cellulose fabrics.

Author Contributions: Conceptualization, J.H.Y.; Investigation, H.Y.C., H.S.C. and B.H.L.; Method-
ology, H.J.Y., H.Y.C., B.H.L. and J.C.W.; Validation, H.S.C. and E.S.; Formal Analysis, H.J.Y. and
J.C.W.; Resources, H.S.C. and H.J.Y.; Data Curation, H.S.C., H.J.Y., J.C.W. and E.S.; Visualization, E.S.
and H.J.Y.; Supervision, J.H.Y.; Project Administration, H.S.C. and H.J.Y.; Writing—Original Draft
Preparation, H.S.C.; Writing—Review and Editing, E.S. and J.H.Y. All authors have read and agreed
to the published version of the manuscript.
Funding: This work was funded by the Ministry of SMEs and Startups Grant funded by the Korean
Government (S2121587).
Institutional Review Board Statement: Not applicable.
Informed Consent Statement: Not applicable.
Data Availability Statement: Data available in a publicly accessible repository.
Conflicts of Interest: The authors declare no conflict of interest.

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