Journal of Dispersion Science and Technology

ISSN: 0193-2691 (Print) 1532-2351 (Online) Journal homepage: http://www.tandfonline.com/loi/ldis20

Effect of Glyphosate Isopropylamine on the

Surface Tension and Surface Dilational Rheology
Properties of Polyoxyethylene Tallow Amine
Surfactant

Ming Li, Fengpei Du, Chong Cao, Baoying Li & Xihai Zhai

To cite this article: Ming Li, Fengpei Du, Chong Cao, Baoying Li & Xihai Zhai (2016) Effect of
Glyphosate Isopropylamine on the Surface Tension and Surface Dilational Rheology Properties
of Polyoxyethylene Tallow Amine Surfactant, Journal of Dispersion Science and Technology,
37:2, 213-221, DOI: 10.1080/01932691.2015.1039022

To link to this article: http://dx.doi.org/10.1080/01932691.2015.1039022

Accepted author version posted online: 26

May 2015.

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 Journal of Dispersion Science and Technology, 37:213–221, 2016
Copyright # Taylor & Francis Group, LLC
ISSN: 0193-2691 print=1532-2351 online
DOI: 10.1080/01932691.2015.1039022

Effect of Glyphosate Isopropylamine on the Surface

Tension and Surface Dilational Rheology Properties
of Polyoxyethylene Tallow Amine Surfactant
Ming Li,1,2 Fengpei Du,2 Chong Cao,2 Baoying Li,1 and Xihai Zhai1
1
Institute of Agricultural Chemicals, Heilongjiang Academy of Agricultural Sciences,
Harbin, PR China
2
Department of Applied Chemistry, College of Science, China Agriculture University,
Beijing, PR China

GRAPHICAL ABSTRACT
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In order to develop the substitutes for polyoxyethylene tallow amine (POEA), the understanding
the interaction of glyphosate isopropylamine and POEA is essential. The surface behaviors
of POEA and POEA in the presence of 1 wt% glyphosate isopropylamine have been investigated
at the air-water interface by the drop shape analysis method. The influences of surface tension,
dilational frequency, and bulk concentration on the surface properties were expounded. The
experiment results show that the adsorption films of POEA behave elastic in nature at low bulk
concentration. With increasing in bulk concentration, the dilational modulus, dilational elasticity,
and dilational viscosity pass through a maximum value, the phase angle increase monotonically.
These phenomena can be attributed to the diffusion-exchange process between the bulk and the
interface. The addition of 1 wt% glyphosate isopropylamine significantly influences on the POEA
surface tension and dilational properties. The dilational modulus, dilational elasticity, and
dilational viscosity obvious decrease in general, and the values of phase angle significant change
after the addition of 1 wt% glyphosate isopropylamine. Glyphosate isopropylamine and POEA
form a new complex in the solution and the surface activity and surface dilational properties
of complex is different from POEA.
Keywords Glyphosate isopropylamine, polyoxyethylene tallow amine, surface dilational
rheology, surface tension

Received 28 March 2015; accepted 6 April 2015.
Address correspondence to Ming Li, Institute of Agricultural
Chemicals, Heilongjiang Academy of Agricultural Sciences,
No. 368, Xue fu Road, Harbin 150086, PR China. E-mail:
mingli655@outlook.com
Color versions of one or more of the figures in the article can
be found online at www.tandfonline.com/ldis.
1. INTRODUCTION
Glyphosate [N-(phosphonomethyl) glycine] has been
described as a ‘‘once in century herbicide’’ because it is con-
sidered environmentally benign to nontarget organisms,
effective at controlling weeds, and can be applied directly
to crops that are genetically modified to be glyphosate
resistant.[1,2] Available glyphosate resistant crops include
corn, soybeans, cotton, canola, and alfalfa.[3–5] It is also
used in urban settings to control weeds and is often applied
to hard surfaces such as roads and sidewalks.[6] Glyphosate

213
 214 M. LI ET AL.
is anionic at physiological pH levels and it is active as salt
with various cations.[7] Isopropylamine salt of glyphosate
is most commonly used as the active ingredient in
commercially available products.
Surfactants are used in pesticide formulations to change
various physical properties and may be added as wetting
agents, emulsifiers, or dispersants.[8] Polyoxyethylene
tallow amine (POEA) is a nonionic surfactant related to
alkylamine ethoxylates (ANEOs). POEA is composed of
a tallow amine moiety, as opposed to the more general
alkylamine, and two chains of repeating ethoxylate units.
The tallow amine moiety is a mixture of amines derived
from palmitic acid (C16 saturated carboxylic acid), oleic
acid (C18 mono-unsaturated carboxylic acid), stearic acid
(C18 mono-saturated carboxylic acid), and other minor
components.[9,10] One of the primary uses of POEA is an
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additive for use with glyphosate isopropylamine formula-
tions. POEA added to glyphosate isopropylamine formula-
tions for physical benefits, studies have also shown that
POEA increases the efficacy of glyphosate isopropylamine
and does so more effectively than other surfactants.[11]
Therefore, POEA is also the specified formulation adjuvant
of glyphosate isopropylamine. However, toxicity studies
have shown POEA to be harmful to a variety of aquatic
wildlife.[11] Lethal concentration for 50% of the population
from 0.097 mg=L for Daphnia magna (water fleas) to
13 mg=L for Ictalurus punctatus (channel catfish) and
Chironomous plumosus (midge larvae).[12–14] Therefore,
the development of substitutes for POEA has been widely
noted in recent years. In view of this, an understanding
the interaction of glyphosate isopropylamine and POEA
is essential.
Our knowledge about the interfacial behavior of
surfactant and pesticide molecules is still limited due to
the lack of both research method and experimental data.
Rheological properties are the main characteristics of
the dynamic properties of an interfacial film.[15–17] The
measurement of dilational rheological behavior of surface-
active molecules adsorbed at the surface has been proven
to be a powerful technique to probe the interfacial
structure of film formed by many kinds of amphiphilic
molecules. It plays an important role in acquiring the
information of molecule interaction, molecule orientation,
characteristics of mixed surfactant and other molecules
films, etc.[18–20]
In this paper, we investigate the surface tension and
dilational rheology properties of adsorbed film at
air-water interface by using the oscillating bubble
method, formed by nonionic surfactant POEA and the
mixture of POEA and 1 wt% glyphosate isopropylamine,
respectively. It may be useful to understand the influence
of glyphosate isopropylamine on the surface behavior
of POEA surfactant and develop the substitutes for
POEA.
2. MATERIALS AND METHODS
2.1. Materials
The Polyoxyethylene tallow amine (POEA) was obtained
from Tanatex Chemicals b. v. The total number of polyox-
yethylene subunits present at the N positions is fifteen
(x þ y ¼ 15) and the purities of the POEA was above 95%.
Glyphosate isopropylamine was obtained from Zhe Jiang
Xinan Chemical Industrial Group Co., Ltd. The structures
and basic molecular formula of POEA and glyphosate
isopropylamine are shown in Figure 1. Ultrapure water
(resistivity >18.2 MX cm) was used in all experiments.
2.2. Surface Tension and Surface Dilational Rheological
Measurements
In this study, the surface dilational viscoelasticity meter
DataPhysics ODG-20 (DataPhysics Instruments GmbH,
Germany) was employed. The working principle is similar
to that of Lucassen and Giles.[21] In this device, the surface
was created by injecting a known volume of air into
an inversed stainless steel needle attached to a gastight
syringe. The tip of the bent needle is immersed in quartz
cuvette containing the surfactant solution. The image of
the air drop was captured by a CCD camera and transferred
to the data acquisition computer where it was digitized and
analyzed by software employing the Laplace equation.
For equilibrium and dynamic surface tension measure-
ments, the surface tension was monitored as a function of
time, and the surface was assumed to be equilibrated when
the surface tension did not change with time. Surface rheo-
logical measurements were performed by oscillating the
bubble to a maximum change of 5% of the original bubble
volume (DA=A ¼ 5%) with frequency of 0.1 Hz. The oscil-
lating frequency can be varied between 0.02 and 0.5 Hz.
The dilational viscoelasticity can be obtained from
measurements of the surface tension response to area
perturbations. The interface dilational modulus is defined
as the ratio of a small change in interface tension to
a change in interface area[22]
dc
e¼ ½1
dlnA
FIG. 1. Chemical structure and basic molecular formula of POEA A)
and glyphosate isopropylamine B).
 EFFECT OF GLYPHOSATE ISOPROPYLAMINE
where e is the dilational modulus, c is the interfacial
tension, and A is area of the interface. e can also be
expressed as the summation of the elasticity and viscosity
contributions
e ¼ ed þ ixgd
where ed is the dilational elasticity and xgd is the dilational
viscosity component that represents a combination of
internal relaxation processes and relaxation due to the
transport of matter between the interface and bulk.
Phase angle h is calculated according to
xgd
tanh ¼
ed
where the h value reflects the responding speed of the
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interface layer to the applied small-area perturbation. In the
absence of relaxation processes, phase angle h is equal to zero
and the interface layer behaves as a purely elastic body.
All experiments were performed at the temperature
298 K. The measurement uncertainty of dilational modulus
is about 1 mN=m.
3. RESULTS AND DISCUSSION
3.1. Surface Tension of POEA
The static surface tension, c (mN=m), of POEA in pure
water versus log C is presented in Figure 2. As shown in
Figure 2, the critical micelle concentration (CMC) of
POEA, which is taken as the concentration at the point
of intersection of the two linear portions of the c – log C
plot, is 4.7  103 wt%. The corresponding surface tension
at CMC is 42.53 mN=m, which indicates that surface
activity of POEA is inferior to other normal surfactants.
The dynamic surface tension measurement has been
proved to be an important method for the adsorption
FIG. 2. Static surface tension versus POEA concentration.
215
kinetics studies of amphiphilic molecules.[23,24] The
dynamic interfacial tension curves of POEA at air=water
interfaces is displayed in Figure 3. As the POEA concen-
tration increases, the surface tension c (t) of POEA
continuously decreases. At low bulk concentration of
½2 POEA (3  104 wt%), the surface tension undergoes a long
relaxation time and the dynamic curve do not appear obvi-
ous turning point, but as the concentration increases, the
long relaxation stage disappears and an obvious turning
point appear at the dynamic curves. The dynamic surface
tension curves are partitioned by two stages of adsorption
with different characteristic relaxation times[25–27]: the
lag stage (the induction stage) (t < s) and the last stage
½3
(t > s). The lag stage of the adsorption are diffusion-
controlled processes, that is, the adsorption is determined
mainly by diffusion of surfactant molecules from the bulk
to the interface. At the last stage, the adsorption is charac-
terized by much lower interfacial tension decreasing rate
due to the steric hindrance to newly adsorbing surfactant
molecules exerted by the yet formed adsorption layer.
The lag stage is characterized by the drastic decrease of
the c (t). This decrease may be ascribed to the considerable
increase of interfacial concentration of adsorbed molecules.
At low bulk concentration of POEA (C ¼ 3  104 wt%),
The decrease of the surface tension lasting a long time
indicated that the adsorption process is controlled not only
by the diffusion of molecules from the bulk to the interface
but also by the relaxation of the already adsorbed
molecules via their rearrangement inside the adsorption
layer. POEA need so long relaxation time for its diffusion
and rearrangement due to its complex hydrophobic part
and large molecular branched structure.
One distinguishes the last stage by the characteristic of
the slow decline in the interfacial tension as time increases.
During this stage, the adsorption achieves its meso-
equilibrium or equilibrium region and the adsorption layer
FIG. 3. Dynamic surface tension curves of POEA at various
concentrations.
 216
reaches a highly condensed state. Long-time molecular
rearrangements and interactions between neighboring
molecules continue to contribute to surface tension
changes.[28] From Figure 3, we can speculate that it is hard
for POEA systems to achieve their equilibrium stages
especially when the concentrations are below 1  102 wt%.
3.2. Frequency Dependence of the Surface Dilational
Properties of POEA
Oscillating frequency is an important factor that
influences dilational properties and the applied oscillating
frequency has a strong effect on the resulting dilational
behavior.[29] Measurements during a range from 0.02 to
0.5 Hz have been carried out to investigate the frequency
dependence of the interfacial dilational properties. In
Figure 4, data of POEA at different surfactant concentra-
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tions are presented.
As seen from Figure 4A and 4C, the dilational modulus
and dilational elasticity of POEA show a similar variation
tendency. Dilational modulus and elasticity increase
gradually with increasing oscillating frequency. At lower
oscillating frequency, surfactant molecules have enough
time to diminish the surface tension gradient resulting from
FIG. 4. Dependence of interface dilational properties on oscillating frequency at various POEA concentration. A) Dilational modulus, B) phase
angle, C) elasticity component, and D) viscous component.
M. LI ET AL.
the deformation of surface. As the oscillating frequency
increases, the restoration of surface tension becomes slower
as compared with the rapid change in interface area,
leading to a higher surface tension gradient. Therefore,
dilational modulus increases with increasing oscillating
frequency.[30]
Phase angle depicts the ratio of the dilational viscosity
and the dilational elasticity. As shown in Figure 4B, as
oscillating frequency increases, the contribution from
the loss modulus will decrease, because of the shorter
time for the relaxation process of diffusion exchange, with
consequent decrease in the value of phase angle.
In general, the viscous behavior relates to the relaxation
processes occurring at or near the interface. Relaxation
processes include the exchange of the interfacial molecules
with the bulk solution, molecular rearrangements occur-
ring within the interface, and so on.[31] The dependence
of dilational viscosity on frequency for POEA solutions is
shown in Figure 4D. The dilational viscosity decrease with
frequency at lower concentrations (C < 5  104 wt%),
however, the opposite is observed at higher concentrations
(C > 1  102 wt%). It means that the maximum of
dilational viscosity of lower concentration appear at the
 EFFECT OF GLYPHOSATE ISOPROPYLAMINE
lower frequency than our experiment, however, for higher
concentration, the characteristic frequency is higher than
the maximum frequency applied in the experiment. The
adsorbed interfacial film of lower concentrations may be
controlled by the rearrangements slow relaxation process,
and the rapid relaxation processes control the interfacial
film of higher concentrations, such as transport of
molecules from the bulk to the interface.
If characteristic frequency of the relaxation process at
the surface layer exceeds the highest oscillating frequency
used in this experiment (0.5 Hz), the curves of log e versus
log x are almost quasilinear. The slopes of curves for
diffusion-controlled relaxation process (the L-T model)
should be lower than 0.5.[32] When an interface has special
structure, the limiting slope of the log e versus log x curve
should be 1.[33] The influence of bulk concentration on the
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slope of log e versus log x curve at air-water interface is
shown in Table 1. In the experimental concentration range,
the slope increases with POEA bulk concentration. The
slope of log e versus log x curve value reflects the visco-
elastic nature of adsorption film, the lower the slope is
the more elastic the film appears.[34] The data in Table 1
indicates that a decrease of elastic contribution to the
dilational modulus.
3.3. Concentration Dependence of the Surface
Dilational Properties of POEA at Air-Water
Interface
As is well known, the surface dilational rheological
parameters depend not only on the oscillating frequency
but also the bulk concentration. Figure 5 shows the
variations of the surface dilational properties versus bulk
concentration for POEA.
From Figure 5A and 5C, it can be seen that the surface
dilational modulus and dilational elasticity pass through
a maximum value with increase in bulk concentration.
According to van den Temple and Lucassen model,[35,36]
an increase of the surfactant concentration has two differ-
ent effects on dilational modulus and dilational elasticity.
On the one hand, the increase of the surface surfactant
molecules with the increasing bulk concentration would
lead to a higher surface tension gradient of the interfacial
TABLE 1
The slopes of log e versus log x with increasing bulk
concentration for POEA
Concentration (wt%) Slope of log e  log x
3  104 0.045
5  104 0.114
1  103 0.195
5  103 0.242
1  102 0.399
217
deforms, which results in an increase in the dilational
modulus and dilational elasticity. On the other hand, the
molecular exchange between bulk and surface is increased
with increasing surfactant concentration. The diffusion of
surfactant molecules from the bulk to the surface can
decrease the surface tension gradient, which creates a
decrease in dilational modulus and dilational elasticity.
Therefore, at low concentrations it is the increasing surface
concentration, whereas the high concentrations it is the
molecular exchange that determines the dilational modulus
and dilational elasticity, respectively. This is why the dila-
tional modulus and dilational elasticity passes through a
maximum with increase in surfactant concentration.
As seen from Figure 5D, the dilational viscosity also
passes through a maximum value with increase in bulk con-
centration. For dilational viscosity, the influence of surfac-
tant bulk concentration has two effects too.[37] Firstly, an
increase in bulk concentration causes an increase of the
surface concentration, which resulting in the number of
the relaxation process. Secondly, the increasing bulk con-
centration produces a decrease in the surface tension gradi-
ent which results from the interface deformation,
decreasing the dilational modulus and also the dilational
viscosity. Therefore, the dilational viscosity may reach a
maximum with increasing bulk concentration. The
maximum of dilational viscosity nearly at CMC concen-
tration, which indicate the relaxation processes mainly be
caused by micelles in bulk.
It is interesting to note that the phase angle variation
trend of POEA is different from other dilational para-
meters. The phase angle monotone increase with increasing
in bulk concentration. This is because the proportion of
elasticity is lessening and the molecular exchange between
bulk and surface is increasing.
3.4. The Surface Tension of the Mixture of POEA and 1
Wt% Glyphosate Isopropylamine
The dependence of the surface tension of the mixture of
POEA and 1 wt% glyphosate isopropylamine on POEA
concentrations is shown in Figure 6. In order to make com-
parisons with glyphosate isopropylamine solutions, the sur-
face tension of pure 1 wt% glyphosate isopropylamine
solution is also shown by a straight solid line in Figure 6.
At low POEA concentrations (below 1  103 wt%), the sur-
face tension of the mixtures fall in below that of pure surfac-
tant and glyphosate isopropylamine solutions. With further
increase in POEA concentrations (above 1  103 wt%), the
surface tension of the mixtures decrease between that of the
pure surfactant and glyphosate isopropylamine solutions.
The surface tension of the mixtures is almost quasilinear
and its slope value obvious small compared with the pure
surfactant.
The surface tension of pure 1 wt% glyphosate isopropyla-
mine between air and water was found to be 72.17 mN=m.
 218
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FIG. 5. Surface dilational properties of POEA as a function of concentration at different oscillating frequency. A) Dilational modulus, B) phase
angle, C) elasticity component, and D) viscous component.
Because of the surface tension of pure water is 72 mN=m
at 298 K, the result indicates that the solution of 1 wt%
glyphosate isopropylamine is no surface active. However,
in the studied bulk concentration range, the surface tension
of the mixtures is significantly different from the pure
FIG. 6. The surface tension of mixture of POEA and 1 wt%
glyphosate isopropylamine as a function of POEA concentrations.
M. LI ET AL.
surfactant solutions. From the surface tension data, we
can speculate that glyphosate isopropylamine and POEA
formed a new complex in the solution and the complex itself
has different surface activity.
3.5. The Surface Dilational Properties of the Mixture of
POEA and 1 Wt% Glyphosate Isopropylamine
Figure 7 shows the influence of 1 wt% glyphosate isopro-
pylamine on surface dilational properties of the interfacial
layer of POEA at 0.1 Hz. From Figure 7, it can be seen that
when POEA and glyphosate isopropylamine coexist in an
experimental system, the concentration dependence of dila-
tional properties of the surface is significantly different
from the pure POEA solution. The dilational modulus,
dilational elasticity and dilational viscosity obvious
decrease in general, and the values of phase angle signifi-
cant change after the addition of 1 wt% glyphosate isopro-
pylamine. The data of dilational properties indicate that
the interfacial layer is not occupied by POEA molecules.
Although POEA is a nonionic surfactant, the tertiary
amine can act as a base and become protonated in neutral
to acidic conditions; the acid dissociation constant (pKa)
of POEA has been reported as a range of 6.5–7.0.[38]
 EFFECT OF GLYPHOSATE ISOPROPYLAMINE 219
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FIG. 7. Effect of 1 wt% glyphosate isopropylamine on surface dilational rheological data of POEA at different concentrations: A) dilational
modulus; B) phase angle; C) elasticity component; D) viscous component.

Therefore, we can speculate that the tertiary amine of

POEA and negative charge of O atom of glyphosate anion
will occur very strong electrostatic interaction. The new
complex molecules are formed in solution, and the glypho-
sate part may be as a hydrophilic group because of the
presence of two hydroxyl radical. The change of surface
tension and dilational properties maybe attributed to the
formation of new surface active molecules at the air-water
interface. This is different from a mixture of conventional
surfactant and compound.
A possible schematic of adsorbed POEA and POEA=
glyphosate isopropylamine molecules at the air-water inter-
face is proposed in Figure 8. In the case of low and moder-
ate surface concentration, for POEA, the two ethylene
oxide group intervene the bulk simultaneously. However
for the new complex, the glyphosate part and two ethylene
oxide groups intervene the bulk together and some of the
excess glyphosate anions dissolve in the isopropylamine
solutions. In the case of high surface concentration, FIG. 8. A schematic illustration of adsorbed POEA A) and POEA=
according to the literature,[39,40] for nonionic surfactant glyphosate isopropylamine B) systems as increasing POEA concentration
contain ethylene oxide group, such as POEA, the closer on the air-water interface.
 220 M. LI ET AL.
packing of ethylene oxide group will form a sublayer, and
the micelles also appear in bulk phase. However, for the
new complex, the glyphosate part and ethylene oxide group
as the hydrophilic group dominate the surface layer
together, and the solubility of POEA molecules may be
enhanced, which results in the weakening of molecular
interaction and the decrease of dilational modulus and
elasticity. On the other hand, the change of surface layer
provide new relaxation processes and change the dilational
viscosity and phase angle.
4. CONCLUSION
In summary, the surface tension and dilational rheologi-
cal behaviors of nonionic surfactant POEA and the mix-
ture of POEA and 1 wt% glyphosate isopropylamine at
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air-water interface are investigated in the present work. It
is revealed from the experimental results that the adsorp-
tion films of POEA behave elastic in nature at low bulk
concentration. With increasing in bulk concentration, the
dilational modulus, dilational elasticity, and dilational
viscosity pass through a maximum value, the phase angle
increases monotonically. The results indicate that the
diffusion-exchange process controls the dilational proper-
ties of surface layer. The addition of 1 wt% glyphosate
isopropylamine significant influences on the POEA surface
tension and dilational properties. The surface tension
of the mixtures is almost quasilinear and its slope value
is obvious small compared with the pure surfactant. The
dilational modulus, dilational elasticity, and dilational
viscosity obviously decrease in general, and the values of
phase angle significant change after the addition of 1 wt%
glyphosate isopropylamine. The results indicate that
glyphosate isopropylamine and POEA form a new complex
in the solution and the surface activity of complex is
different from POEA. The dilational data we obtained can
expound the arrangement of interfacial POEA and the
complex of POEA=glyphosate isopropylamine molecules
in detail and are very helpful to understand the interaction.
FUNDING
We gratefully acknowledge special fund for agro-scientific
research in the public interest of china (201103024).
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