Journal of Molecular Liquids 287 (2019) 110932

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Journal of Molecular Liquids

journal homepage: www.elsevier.com/locate/molliq

Effects of reactive dye structures on surface tensions and viscosities of

dye solutions
Kun Zhang 1, Ruyi Xie 1, Kuanjun Fang ⁎, Weichao Chen, Zhen Shi, Yanfei Ren
Fiber Materials and Modern Textiles of the Growing Base for State Key Laboratory, Qingdao University, 308 Ningxia Road, Qingdao 266071, China
School of Textiles & Clothing, Qingdao University, 308 Ningxia Road, Qingdao 266071, China
Collaborative Innovation Center for Eco-Textiles of Shandong Province, 308 Ningxia Road, Qingdao 266071, China

a r t i c l e i n f o a b s t r a c t

Article history: In textile inkjet printing, the surface tension and viscosity of the reactive dye solution are two important physical
Received 5 March 2019 properties to control the droplet formation. In this work, surface tensions and viscosities of four reactive dye so-
Received in revised form 21 April 2019 lutions with/without surfactants and organic solvents were tested to investigate the effect of reactive dye struc-
Accepted 6 May 2019
tures on them. The results show that on dye molecules the hydrophobic groups not linking to hydrophilic groups
Available online 7 May 2019
or large in size can lead to a decrease in the surface tension and an increase in the viscosity. Moreover, droplet
Keywords:
formations of these solutions are observed. It is found that reactive dye structures can also affect the droplet for-
Reactive dye mation through influencing the surface tension and viscosity of dye solutions. This study is significant for
Surface tension adjusting the surface tension and viscosity of the reactive dye solution according to dye structures.
Viscosity © 2019 Elsevier B.V. All rights reserved.
Dye structure
Droplet formation

1. Introduction
Recent years, inkjet printing technology has rapidly developed in
textile field as it has many advantages over conventional printing ap-
proaches, such as reduced material wastage, low cost, eco-friendly, as
well as quickly responding to commercial demands [1–6]. However,
poor droplet formations, particularly satellite droplets, are still serious
problems since they result in many problems in practical production
such as low product resolution, printer device damage and environmen-
tal pollution [7,8].
Many studies have shown that the surface tension and viscosity of
the solution have vital influence on break position of droplet at the noz-
zle, droplet dimension and dropping velocity as well as satellite drops
generation [9–17]. Therefore, grasping the surface tension and viscosity
precisely is the key to control the droplet formation. Virtually, the sur-
face tension and viscosity are both macro behaviors of intermolecular
interactions. Surface tension, a dynamic process, is related with the sol-
ute concentration at air-liquid interface [11]. Hydrophobic interaction is
the cause of the decrease in surface tension. When a fresh interface is
formed, the surface tension of the new interface approximately equals
⁎ Corresponding author at: Fiber Materials and Modern Textiles of the Growing Base for
State Key Laboratory, Qingdao University, 308 Ningxia Road, Qingdao 266071, China.
E-mail address: 13808980221@163.com (K. Fang).
1
Both authors contributed equally to this work.
that of the solvent. Subsequently, the surface tension decreases as the
solute molecules adsorb at the interface, until the adsorption reaches
an equilibrium [18]. Viscosity is determined by intermolecular forces,
such as van der Waals forces, hydrogen bond and electrostatic interac-
tion [19–21]. Thence, the type and structure of the solute is an impor-
tant factor affecting the surface tension and viscosity of the solution.
Nowadays, the surface tensions and viscosities of surfactant, organic sol-
vent, and polymer solutions have been extensively studied [22–33]. Be-
sides, studies on surface properties of acid dyes have also been reported
[34]. Nevertheless, there are few papers on the surface tensions and vis-
cosities of reactive dye solutions. Reactive dyes are most commonly
used in inkjet printing of cellulose fabrics as they have broad color
gamut, high washing and rubbing fastness [35–37]. Consequently, it is
very significant to investigate the surface tensions and viscosities of re-
active dye solutions.
In this work, surface tensions and viscosities of four reactive dye
aqueous solutions were measured to investigate the effect of reactive
dye structures on them. Surfactants and organic solvents are widely
used to adjust the surface tension and viscosity of dye solutions [38]. It
is important to study whether dye structures still affect the surface ten-
sions and viscosities of reactive dye solutions after adding surfactants
and organic solvents. Four dye solutions with same content of a surfac-
tant and an organic solvent were prepared and their surface tensions
and viscosities were tested. Moreover, influences of surface tensions
and viscosities of reactive dye solutions on droplet formation were

https://doi.org/10.1016/j.molliq.2019.110932
0167-7322/© 2019 Elsevier B.V. All rights reserved.
2 K. Zhang et al. / Journal of Molecular Liquids 287 (2019) 110932

Table 1 sulfonate groups. Four desalting reactive dyes, C.I. reactive orange 13
Chemical structures and some information of the four reactive dyes. (O-13), C.I. reactive red 218 (R-218), C.I. reactive yellow 95 (Y-95)
Name Chemical structure CAS Relative and C.I. reactive blue 49 (B-49), were purchased from Taiwan
molecular mass Yongguang Co., Ltd. Table 1 shows the structures of the four reactive
O-13 12225-85-3 762 dyes. Twice distilled water was used in this experiment. The surfactant
(surfynol 465) was provided by Yuyue Home Textiles Co., Ltd. The or-
ganic solvent was 1,3-propanediol (analytical purity) purchased from
Sinopharm Chemical Reagent Co., Ltd.
R-218 113653-03-5 856

2.2. Preparation of dye solutions

Y-95 71838-97-7 751 All dye solutions were prepared in a 250 mL volumetric flask. Dye
concentrations of dye aqueous solutions ranged from 10 mmol/L to
80 mmol/L. Certain amounts of dyes were accurately weighed through
an AL104 precision electronic balance and then put into a 250 mL beaker
B-49 12236-92-9 882
with a little water. 0.9 g of surfactants and organic solvents were added
into the beaker and fully stirred. A little of water was added into the bea-
ker and fully stirred. Then, the solution was poured into a 250 mL volu-
metric flask. Distilled water was used to wash the beaker three times
and then poured into the volumetric flask. The dye solution was pre-
explored by observing the droplet falling process of four dye solutions pared successfully after constant volume in the volumetric flask. Finally,
with/without a surfactant and an organic solvent. dye solutions were filtered by a polypropylene fiber membrane with the
hole diameter of 0.22 μm. For comparison, the dye solutions without
2. Experimental section surfactants and organic solvents were prepared in the same way.

2.1. Materials 2.3. Dynamic surface tension tests

Reactive dyes used in textile inkjet printing must be salt-free, of The dynamic behaviors of the reactive dyes were studied using the
good water solubility and not easily hydrolyzed. Therefore, all reactive maximum bubble pressure method. A SITA t-60 surface tensiometer
dyes used in this work are monochlorotriazine dyes with three was used for all samples' dynamic surface tension measurements [24].

Fig. 1. Variation of the surface tension of dye solutions with dye concentration and bubble lifetime. (a), Surface tension variation with dye concentration. Bubble lifetime is 60 s. (b), (c),
Surface tension variation with bubble lifetime. Dye concentrations of (b) and (c) are both 80 mmol/L. Bubble lifetime ranges from 0.03 s to 60 s. Dye solutions of (a) and (b) contain no
additives, while dye solutions of (c) contain a surfactant (3.6 g/L) and an organic solvent (450 g/L).
 K. Zhang et al. / Journal of Molecular Liquids 287 (2019) 110932 3

All samples were measured at 25 ± 0.5 °C. The bubble lifetime refers to head. All observations were performed at room temperature at a jet fre-
the time from the bubble initially forming at the capillary head to the quency of 20 kHz.
bubble radius equal to the capillary radius, which ranges from 0.03 s
to 60 s. 3. Result and discussion

2.4. Viscosity measurements 3.1. Surface tensions

Viscosities of dye solutions were measured by the rotation method.
All samples were tested at 25 ± 0.5 °C using a zero rotor by a Brookfield
DV-3 T rheology tester. The rotating speed of rotor was 60 rpm.
2.5. Droplet formation observation
The droplet formations of all samples were observed through a
Fanjiang drops observed instrument which installs a Kyocera printing
Surface tensions of four dye aqueous solutions were measured to in-
vestigate the effects of reactive structures on the surface tensions. In
Fig. 1a, the surface tension of R-218 solution decreased obviously with
the increase of dye concentration. The surface tension of B-49 solution
also decreases but not obviously as the R-218 solution. For O-13 and
Y-95 solutions, their surface tensions did not exhibit apparent changes
at different concentrations. Fig. 1b showed the changes of surface ten-
sions for different dye solutions and pure water with the prolonging of

Fig. 2. Schematic diagram of the distribution of (a) R-218 molecules, (b) B-49 molecules, (c) R-218 and surfactant molecules, (d) B-49 and surfactant molecules, and (e) surfactant
molecules at the air-solution interface.
4 K. Zhang et al. / Journal of Molecular Liquids 287 (2019) 110932

Fig. 3. Molecule-length schematic diagram of (a) R-218 and (b) B-49. The molecular models are simulated by a Chem3D and then optimized by the MM2 calculation.

bubble lifetime. The surface tension of pure water remained unchanged.
Surface tension of R-218 and B-49 decreased with the increase of bubble
lifetime. R-218 showed faster declining rate. Y-95 solution exhibited
slightly decline. Surface tension of O-13 solution was similar to that of
water and appeared little change. Surface tension is determined by sol-
ute concentration at air-solution interface. According to the above re-
sult, it can be concluded that concentrations of R-218 and B-49
increased at the air-solution interface as the dye concentration in-
creased or the bubble lifetime prolonged, while O-13 molecules and
Y-95 molecules hardly adsorbed at air-solution interface. This phenom-
enon may be caused by the chemical structures of reactive dye
molecules.
Distribution of hydrophobic and hydrophilic groups on dye mole-
cules plays a key role in adsorption of dye molecules at air-solution in-
terface. In aqueous solutions, hydrophobic groups on dye molecules
such as aromatic ring, alkane usually results in the water molecules
around them forming an ice-like structure. Water molecules in the
ice-like structure have a longer motion cycle than bulk water molecules
[39–41]. Hydrophilic groups such as sulfonates which can be hydrated
with water molecules or polar groups which can form hydrogen
bonds with water molecules can break this structure and endow the
water molecules vigorous again [42]. On a R-218 molecule, there is a
benzene ring and an ethyl group without any hydrophilic group
connecting (Table 1). The benzene ring and ethyl group can result in
23 water molecules and 8 water molecules fixing and forming the ice-
like structures, respectively [43,44]. That can reduce the chaos of R-
218 solution system and make the system instability. To maintain disor-
der of R-218 solution, the benzene ring and ethyl group have to adsorb
at air-solution interface to release the water molecules from the ice-like
structure as shown in Fig. 2a. The process is driven by entropy.
Moreover, the size of hydrophobic groups is another important fac-
tor influencing the motion cycle of hydration water molecules adjacent
to the functional groups [45–47]. A B-49 molecule contains an anthra-
quinone group whose size is larger than the benzene group and the
naphthalene group. Hydrophilic groups connecting to the anthraqui-
none group may not completely break the ice-like structure, which re-
sults in B-49 molecules adsorbing at air-solution interface as depicted
by Fig. 2b. The surface tension of R-218 solution decreased more obvi-
ously than that of B-49 solution. The reason is longer hydrophobic
chains on R-218 molecules than B-49 molecules can stretch out of the
air-solution interface. As shown in Fig. 2a-b, a benzene ring and an
ethyl group on a R-218 molecule can adsorb at air-solution interface
while only a small part of the anthraquinone on a B-49 molecule can
stretch out of the water due to hydrophilic groups such oxygen, amino
and sulfonate group linking to the anthraquinone group. Thus, R-218
has higher efficiency than B-49 to reduce surface tension. Besides, sur-
face area admitting dye molecules to adsorb is limited. Molecular length
of B-49 is far longer than that of R-218, as shown in Fig. 3, which might
result in less number of B-49 molecules than R-218 molecules at the air-
solution interface.
Fig. 1c illustrates the surface tensions of four dye solutions after
adding a surfactant and an organic solvent. It can be seen that at the
same bubble lifetime, the surface tension of B-49 solution is the largest,
that of R-218 solution is the second. The surface tension of O-13 solution
is almost same with that of Y-95 solution, which are lower than those of
B-49 and R-218. The order of surface tensions of dye solutions with a

Fig. 4. Viscosity of (a) dye solutions without additives, and (b) dye solutions after adding a surfactant and an organic solvent. Dye concentrations of (b) are all 80 mmol/L. And the
surfactant and the organic solvent concentrations of (b) are 3.6 g/L and 450 g/L, respectively.
 K. Zhang et al. / Journal of Molecular Liquids 287 (2019) 110932
surfactant and an organic solvent is not consistent with that of dye solu-
tions without additives. That may be attributed to the lower surfactant
concentrations at the air-solution interfaces of R-218 and B-49 solutions
than those of O-13 and Y-95 solutions, as shown in Fig. 2c-e. R-218 and
B-49 molecules can adsorb at the air-solution interfaces, but O-13 and
Y-95 molecules can't. The efficiency of R-218 molecules or B-49 mole-
cules to reduce surface tension is undoubtedly lower than that of the
surfactant. As a result, O-13 and Y-95 solutions with surfactants exhib-
ited much lower surface tensions than R-218 and B-49 solutions.
3.2. Viscosities
Viscosities of four dye solutions without additives are shown in
Fig. 4a. Viscosities of the four dye solutions increases more and more
quickly with dye concentration increasing from 10 mmol/L to
80 mmol/L. That may be caused by the increasing van der Waals forces
between the dye molecules. At the same dye concentration, viscosity of
B-49 is the largest, and that of R-218 solution is the second only to the B-
49 solution. Viscosities of O-13 and Y-95 solutions are almost same to
each other and lower than those of R-218 and B-49 solutions. As
shown in Table 1, relative molecular masses of B-49 (882) and R-218
(856) are larger than that of O-13 (762) and Y-95 (751). It means that
B-49 and R-218 molecules have stronger van der Waals forces than O-
13 and Y-95 molecules. Moreover, in aqueous solution, it was difficult
for dye molecules to approach each other due to electrostatic repulsion
between sulfonate ions. However, as mentioned earlier, the R-218 mol-
ecule contains a benzene ring without sulfonate group connecting.
Thus, R-218 molecules might approach to each other through hydro-
phobic interactions and form a π\\π bond between the benzene rings,
as shown in Fig. 5a. Similarly, B-49 molecules might contact with each
other through the anthraquinone groups and form a π\\π bond finally,
as shown in Fig. 5b. Due to lager size of anthraquinone group than the
benzene ring, π-π interaction between anthraquinone groups is stron-
ger than that between benzene rings. Therefore, viscosity of B-49 solu-
tion is obviously higher than that of R-218 solution, and viscosities of
O-13 solution and Y-95 solution are the smallest.
Fig. 4b demonstrates the viscosities of the four dye solutions after
adding a surfactant and an organic solvent. It can be seen that the vis-
cosities of four solutions were all beyond 4 mPa·s, far higher than that
of dye solution without additives. That is caused by the high viscosity
of organic solvent. However, the order of viscosities of the dye solutions
with additives from high to low is same as those of the dye solutions
without additives. Viscosity of B-49 solution is the highest. R-218
solution's viscosity is higher than that of O-13 solution and Y-95 solu-
tion. Viscosities of O-13 solution and Y-95 solution are same to each
other.
Fig. 5. Schematic graph of (a) R-218 molecules and (b) B-49 molecules forming π-π bonds.
5
3.3. Droplet formations
Droplet formations of four dye solutions with/without a surfactant
and an organic solvent are shown in Fig. 6. Fig. 6a~d show the droplet
formations of O-13, R-218, Y-95 and B-49 solutions, respectively. It is
obvious that O-13 and Y-95 solutions form more satellite drops than
R-218 and B-49 solutions. On the one hand, viscosities of R-218 and B-
49 solutions are larger than those of O-13 and Y-95 solutions. That de-
notes breakup of R-218 and B-49 droplets is more difficult than O-13
and Y-95 droplets. On the other hand, according to Jang D et al., high
surface tension detached the retreating filament from the rapidly falling
primary droplet, forming satellite droplets [16]. In falling process, R-218
molecules and B-49 molecules can adsorb at the air-solution interface
reducing the surface tension. Therefore, R-218 and B-49 solutions can
form less satellite drops than O-13 solution and Y-95 solution.
Droplet formations of O-13, R-218, Y-95 and B-49 solutions with a
surfactant and an organic solvent are depicted in Fig. 6e~h, respectively.
It can be seen that the droplet formations of four dye solutions were all
improved after adding a surfactant and an organic solvent. In the initial
stage, four dye solutions all form one satellite droplet behind the head
droplet. However, in falling process, satellite droplet of R-218 solution
can catch up the head droplet and form one droplet finally while the sat-
ellite droplets of other solutions can't. That means the droplet formation
of R-218 solution is better than those of other solutions. Droplet figure
of O-13 solution is very similar to that of Y-95 solution because their
similar surface tensions (Fig. 4b) and viscosities (Fig. 1c). According to
this result, when preparing reactive dye solutions used for inkjet print-
ing, to obtain the optimal surface tension and viscosity the amount of
the surfactant and the thicker should be appropriately adjusted based
on different reactive dye structures.
4. Conclusion
Chemical structures of reactive dyes have different effects on the
surface tension and viscosity of the dye solution. In this work, R-218
can reduce the surface tension of the solution obviously. B-49 can also
decrease the surface tension of the solution although not obviously
like R-218. O-13 and Y-95, however, have little influence on the surface
tension of their solutions. As for the viscosity, B-49 has the greatest in-
fluence on the viscosity of the solution, followed by R-218, and O-13
and Y-95 have the least influence on the viscosity. In conclusion, hydro-
phobic groups large in size or not attached to hydrophilic groups on re-
active dye molecules can adsorb at air-solution interface to reduce the
surface tension of solutions. Besides, these hydrophobic groups can in-
teract with each other more easily than those hydrophobic groups
linking to the sulfonate groups, increasing the viscosity of the solution.
6 K. Zhang et al. / Journal of Molecular Liquids 287 (2019) 110932

Fig. 6. Droplet formations of the four dye solutions. (a-d), Droplet formations of O-13, R-218, Y-95 and B-49 solutions without additives, respectively, and (e-h), droplet formations of
corresponding solutions with a surfactant and an organic solvent. Dye concentrations of all solutions are 80 mmol/L. Surfactant concentration and organic solvent content are 3.6 g/L
and 450 g/L, respectively. Jetting frequency is 20 kHz.

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