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FOCUS: Textile Detergents and Body Care Products

y Yu Nagai1 , Natsumi Togawa2 , Yumiko Tagawa3 and Keiko Gotoh2

Comparison of Cleaning Power Between


Alcohol Ethoxylates or Methyl Ester
Ethoxylates Having Different EO Chain
Lengths and a Common Anionic
Surfactant
Tenside Surfactants Detergents downloaded from www.hanser-elibrary.com by Purdue University Library TSS on August 20, 2016

Cleaning power of different surfactants was investigated using a gerührt (mechanisch bewegt) wurden. Die Menge der auf dem
model detergent system consisting of a PET film and stearic acid. PET-Film abgeschiedenen Stearinsäure wurde vor und nach der
Surfactants used were alcohol ethoxylates (AE, C12) and methyl Reinigung mittels digitaler Verarbeitung der mikroskopischen
ester ethoxylates (MEE, C12) with different ethylene oxide (EO) Aufnahmen erhalten, woraus die Schmutzentfernungsleistung
chain lengths. For comparison with these nonionic surfactants, berechnet wurde. Die Oberflächenspannung (c) und der Kon-
anionic surfactant, sodium alkyl sulfate (AS, C12), was chosen. taktwinkel (h) der Tensidlösung auf dem PET-Film wurden mit
After depositing stearic acid, the PET film was cleaned in aque- der Methode des hängenden bzw. liegenden Tropfens bestimmt.
ous surfactant solutions by applying stirring as a mechanical ac- Die kritische Mizellbildungkonzentration (cmc), die Oberflä-
tion for soil removal. The amounts of stearic acid deposited on chenspannung (c) und der Kontaktwinkel (h) oberhalb der cmc
the PET film before and after the cleaning were obtained by bin- den nichtionischen Tenside fielen mit abnehmender EO-Ketten-
ary processing of microscopic images of the PET film surface, länge. Die Entfernung der Stearinsäure nahm mit steigender
For personal use only.

from which the removal efficiency was calculated. The surface Tensidkonzentration zu. Eine weitere ansteigende Entfernung
tension c and the contact angle on the PET film h of the sur- oberhalb der cmc konnte für AE und MEE, deren EO-Kettenlän-
factant solution were measured by the pendant drop and the gen 10 waren, beobachtet werden. Die in allen Systemen erziel-
sessile drop method, respectively. For the nonionic surfactants, te Entfernungseffizienz hatte eine gute Beziehung zur Oberflä-
critical micelle concentration, cmc, and c and h above cmc de- chenspannung und Kontaktwinkelzwischen der Stearinsäure
creased with decreasing EO chain length. The removal efficiency und dem PET-Film. Das deutete daraufhin, dass die Durchdrin-
of stearic acid increased with increasing surfactant concentration gung der Tensidlösung zwischen der Stearinsäure und dem
and further increase in the removal above cmc was observed in PET-Film ein dominanter Faktor für die Schmutzentfernung in
the cases of AE and MEE with EO chain length of 10. The re- dem gegebenen System war.
moval efficiencies obtained in all systems had good relation
with both c and h, indicating that the penetration of the surfac- Stichwörter: Waschkraft, nichtionisches Tensid, EO-Ketten-
tant solution between stearic acid and the PET film in the con- länge, Stearinsäure, mikroskopische Bildanalyse
tact zone was a dominant factor in the soil removal in the pres-
ent system.
1 Introduction
Key words: Detergency, nonionic surfactant, EO chain length,
stearic acid, microscopic image analysis In recent years, laundry detergents have been developed
from the viewpoints of resource-saving and energy-saving
as well as high performance. For the purpose, ultra-concen-
Vergleich der Waschkraft zwischen Alkoholethoxylaten trated liquid detergents, which are less dosage, are increas-
und Methylesterethoxylaten mit unterschiedlichen EO-Ket- ing all over the world [1, 2]. Ethoxylate nonionics, which
tenlängen und einem üblichen anionischen Tensid. Die have relatively a low critical micelle concentration, cmc, are
Waschkraft von verschiedenen Tensiden wurde mittels eines formulated as main ingredients in ultra-concentrated liquid
Modellwaschsystems bestehend aus einem PET-Film und Stea-
detergents. They are low foaming, work well in hard water
rinsäure untersucht. Bei den eingesetzten Tensiden handelte es
at low temperatures, and have good solubilization-emulsifica-
sich um C12-Alkoholethoxylate (AE) und um C12-Methylestere-
tion power.
thoxylate (MEE), deren EO-Ketten unterschiedlich lang waren.
Ethoxylated nonionic surfactant in laundry detergents is
Diese nichtionischen Tenside wurden mit dem anionischen Ten-
mostly biodegradable alcohol ethoxylates (AE), which can re-
move sebum efficiently at low temperature [3 – 6]. AE can
sid Natriumdodecylsulfat (C12-AS) verglichen. Nach Abschei-
maintain enzyme stability in the presence of anionic surfac-
dung der Stearinsäure wurde der PET-Film in wässrigen Tensid-
tant [7] and therefore has excellent compatibility with en-
lösungen gereinigt, wobei die Lösungen zur Schmutzentfernung
zyme in laundry detergents. [8].
1
School of Natural Science and Ecological Awareness, Nara Women’s University Other nonionic ethoxylates are methyl ester ethoxylates
2
(Kita-uoya-nishi-machi, Nara 630-8506, Japan) (MEE), which are manufactured by direct addition of ethy-
Faculty of Human Life and Environment, Nara Women’s University (Kita-uoya- lene oxide (EO) to fatty acid methyl ester. They are highly
nishi-machi, Nara 630-8506, Japan)
3
Faculty of Business Management, Osaka Sangyo University (Nakagaito, Daito, safe and better biodegradable. In addition, MEE reveal favor-
Osaka 574-8530, Japan) able surfactant performances and solution properties such

Tenside Surf. Det. 51 (2014) 2 ª Carl Hanser Publisher, Munich 113


Yu Nagai et al.: Comparison of cleaning power between alcohol ethoxylates or methyl ester ethoxylates

as better foam breakability and smaller gel range in compar- 2.2 Cleaning tests
ison with AE [9, 10]. The performance of MEE is attributed
to its chemical structure which has \bend" because of its es- Prior to the soil removal experiment, stearic acid was de-
ter bond. It has been reported that MEEs can remove oleic posited on the PET film ((10 · 40) mm2) by spraying
acid from deep inside fibers and that consequently shows 7.5 · 10–5 dm3 of acetone solution (5 g/dm3) uniformly.
superior detergency [11]. After aging for 24 h in a room at 20 8C and 65 %RH, the
For these ethoxylated nonionics, the adsorbing power, the PET film was cleaned by immersing perpendicularly in a
rinsing ability and the solubility can be controlled by chang- 0.02 dm3 surfactant solution. As a mechanical action for soil
ing hydrophilic EO chain length. Although it has been re- removal, stirring action with rotation speed of 600 rpm was
ported that maximum detergency was found around EO7 – applied with a magnetic stirrer bar (1.5 mm diameter ·
10 for alkyl chain lengths of 12 [12], the effect of EO chain 10 mm). The washing temperature was set at (25 € 1) 8C.
length on the detergency was not systematically investi- After the cleaning, the PET film was dried in air.
gated. With respect to the difference in detergency between The soil removal efficiency was evaluated by binary pro-
AE and MEE, very few experimental investigations have cessing of microscopic images of the PET films before and
been carried out in the same experimental system [13]. after the cleaning [14]. The system used consisted of a
Tenside Surfactants Detergents downloaded from www.hanser-elibrary.com by Purdue University Library TSS on August 20, 2016

In this study, we evaluated the removal of stearic acid biological microscope (CKX41, Olympus, Japan), a Com-
from the polyethylene terephthalate (PET) substrate in aque- plementary metal-oxide-semiconductor (CMOS) camera
ous nonionic ethoxylate solutions. C12AE and C12MEE with (Lu275, Lumenera, Canada), image tiling software (e-Tiling,
different EO chain lengths and anionic sodium dodecyl sul- Mitani Corporation, Japan) and 2D image analysis software
fate were used and the detergency evaluation was performed (WinRoof Ver. 6, Mitani Corporation, Japan). Microscopic
by microscopic image analysis of the PET substrate before images within the same field of view before and after the
and after the cleaning [14]. The obtained detergency was dis- cleaning were obtained over five different areas (0.90 mm2
cussed in terms of the surface tensions and the contact an- per area) located 10 mm from the lower edge of the PET
gles on the PET substrate of the surfactant solutions. film. The microscopic image of the soil deposited on the
PET film was converted from an original gray-scale digital
image with 256 possible intensity values to a binary image
using a suitable threshold level (*105 in most cases). The
2 Experimental
removal efficiency was calculated from the changes in the
total area of stearic acid deposited on the PET film due to
2.1 Materials cleaning. The cleaning tests were repeated 5 – 10 times un-
For personal use only.

der the same experimental conditions.


A biaxially oriented PET film with a thickness of 188 lm
(EMBLET SA-188, Unitika, Japan) was used as a model sub- 2.3 Surface tension and contact angle measurements
strate. Prior to use, the film was purified twice in water with
ultrasound. As a model oily soil, long-chain fatty acid, stearic The surface tension of the surfactant solution was measured
acid, was chosen. by the pendant drop technique using a video contact angle
The nonionic surfactants used were alcohol ethoxylates system equipped with a CCD camera (VCA 2500, AST Pro-
(AE, C12) and methyl ester ethoxylates (MEE, C12) with eth- ducts Inc., USA). The solution was dispensed from the mi-
ylene oxide (EO) chain length of 10, 15 and 20, which were crosyringe to form a pendant drop, which was made as big
provided from Lion Corporation (Japan). Active ingredient as possible without letting it fall off the tip of the needle.
and EO adduct distribution of these nonionic surfactants de- The surface tension was determined by pendant drop image
termined by high-performance liquid chromatography analysis through video-image digitization and numerical
(HPLC) [9] are given in Table 1. The anionic surfactant, so- curve-fitting using the Laplace equation of capillarity [15].
dium alkyl sulfate (AS, C12, Wako Pure Chemical Indus- The contact angle of the surfactant solution on the PET
tries, Ltd., Japan) was also used. Sodium chloride was used film was measured by the sessile drop technique using the
as neutral salt. above video contact angle system. The contact angles mea-
Chemicals used were extra-pure-grade reagents, which sured 1 s after placing a 2 – 3 ll water drop was determined
were utilized without further purification. The water was as the approximate value of the advancing angle [16].
purified (resistivity of 18 MX cm) using a direct-Q UV appa- The surface tension and the contact angle measurements
ratus (Millipore, USA). were repeated 5 – 10 times for the same surfactant solution
in a room maintained at 20 8C and 65 %RH.

2.4 High-performance liquid chromatography (HPLC)

Nonionic Active EO distribution/% The sample solutions were prepared as follows: adding ex-
surfactants ingredient/% cess amount of stearic acid to the AE (EO10 or EO20) solu-
AE (EO10) 99.9 80 tion at 3 times cmc, and stirring with rotation speed of
300 rpm at 25 8C for 24 h [17]. The sample solution was
AE (EO15) 99.9 73 filtered using nitro-cellulose sheets with 0.8 lm in pore
AE (EO20) 99.8 57 diameter.
The analyses of the filtrate containing surfactant micelles
MEE (EO10) 90.9 70
or stearic acid/methanol solution (1 g/dm3) were carried out
MEE (EO15) 90.8 65 by high-performance liquid chromatography (HPLC). The
MEE (EO20) 90.0 57 system consists of a LC-10ADvp pump, a CTO-10ASvp col-
umn oven and a SPD-M10Avp (wavelength: 215 nm) detec-
Table 1 Active ingredient, EO adduct distribution for nonionic surfactant tor (Shimadzu Corporation, Japan). The column used was
samples Inertsil ODS (2.1 mm · 150 mm, 3 lm, GL Sciences). The

114 Tenside Surf. Det. 51 (2014) 2


Yu Nagai et al.: Comparison of cleaning power between alcohol ethoxylates or methyl ester ethoxylates

chromatographic run was carried out at a flow rate 2.5 · 10–4 3.3 Soil removal
dm3/min with a mobile phase consisting 5 % aqueous solu-
tion of phosphoric acid and 95 % methanol. The injection The removal efficiency of stearic acid from the PET film in
volume was 2.5 · 10–5 dm3 and the column temperature 1.4 · 10–4 mol/dm3 AE (EO10) solutions is shown in Fig. 3
was held at 40 8C. as a function of wash time. The soil removal increased with
time and the apparent detergency equilibrium was achieved
3 Results and Discussions

3.1 Surface tension

Figure 1 shows the surface tension vs. logarithm of surfac-


tant concentration curves. As expected, the surface tension
decreased linearly with increasing concentration. When the
cmc was reached, the surface tension remained almost con-
stant value, ccmc. The cmc was determined from the inter-
Tenside Surfactants Detergents downloaded from www.hanser-elibrary.com by Purdue University Library TSS on August 20, 2016

section of the linear concentration-dependent section and


the concentration-independent section. By the application
of the Gibbs equation to the c – logC relationships in Fig. 1,
surface excess concentration of surfactant, C, and the effec-
tive area occupied by each adsorbed surfactant molecule or
ion, A, were determined [3].
The obtained values of cmc, ccmc, C, and A are presented
in Table 2. The cmc of the nonionic surfactants, AE and
MEE, were at least one order of magnitude smaller than that
of the anionic surfactant, AS. The ccmc as a measure of the
surface tension-lowering ability of surfactant decreased with
decreasing EO chain length. The values of ccmc for EO15
nonionic surfactants were close to that for AS. In the case
of nonionic surfactants with the same EO chain length, the
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cmc was large and the ccmc was small for MEE in compari-
son of A E. Cox and Weerasooriya [13] who have found the
same tendency and explained this by the ester carbonyl
moiety and a terminal methoxy group of MEE. In addition,
the C was larger and therefore, the A was smaller for AE
with relatively linear molecular structure than for MEE with
bent and curved molecular structure [10]. The value of A was
found to increase linearly with increasing EO chain length
in both cases of AE and MEE. Similar relation has been re-
ported by Rosen et al. [18] for AE with EO chain lengths of
2 – 8.

3.2 Contact angle

Figure 2 shows the contact angles of the surfactant solutions


on the PET film as a function of surfactant concentration. In
all cases, the angle decreased with increasing concentration
and reached an almost constant value above cmc, hcmc. The
values of hcmc as a measure of the wettability-enhancing abil-
ity of surfactant are given in Table 2, which decreased with Figure 1 Plots of surface tension, c, against logarithm of surfactant concen-
decreasing EO chain length of the nonionic surfactants. tration, C

Surfactants cmc/mol dm–3 C/mol m–2 A/nm2 ccmc/mNm–2 hcmc/degree


AS 8.0 · 10–3 2.9 · 10–6 0.56 38 49
AE (EO10) 1.4 · 10–4 7.1 · 10–6 0.23 35 46
AE (EO15) 2.2 · 10–4 3.5 · 10–6 0.46 39 46
AE (EO20) 2.4 · 10–4 2.3 · 10–6 0.70 44 54
MEE (EO10) 2.9 · 10 –4
4.3 · 10 –6
0.37 33 43
MEE (EO15) 3.2 · 10–4 3.3 · 10–6 0.48 39 50
MEE (EO20) 3.6 · 10–4 2.0 · 10–6 0.81 41 52

Table 2 Critical micelle concentration, cmc, surface excess concentration, C, occupied surface area per absorbed surfactant molecule, A, surface tension above
cmc, ccmc , and contact angle on the PET film above cmc, hcmc , for anionic and nonionic surfactants

Tenside Surf. Det. 51 (2014) 2 115


Yu Nagai et al.: Comparison of cleaning power between alcohol ethoxylates or methyl ester ethoxylates

after cleaning of 5 min. Therefore, the washing time was set


as 5 min in the experiments mentioned below.
Figure 4 presents the effect of surfactant concentration on
the removal efficiency of stearic acid. The removal was pro-
moted by the addition of the surfactants, depending on EO
chain length (EO10 > EO15 > EO20) for the nonionic surfac-
tants. The soil removal was almost constant above cmc for
the anionic surfactant AS and EO15 and EO20 nonionic sur-
factants, whereas further increase in the soil removal above
cmc was observed for EO10 nonionic surfactants.
In general, rolling up, emulsification and solubilization
are usual mechanisms in the cleaning of oily contaminants
from solid surfaces in aqueous surfactant solutions [19].
However, rolling up and emulsification do not take place in
the displacement of solid soil such as stearic acid with melt-
Tenside Surfactants Detergents downloaded from www.hanser-elibrary.com by Purdue University Library TSS on August 20, 2016

ing point of 70.5 8C [20].


Above cmc, solubilization, the dissolution of the oily con-
taminant directly into micelle, can efficiently remove oily
soil. The increase in the soil removal observed for EO10
nonionic surfactant solutions above cmc (see Fig. 4) may be
caused by such solubilization mechanism. However, in
HPLC chromatograms (Fig. 5), one major peak appeared at
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Figure 2 Plots of contact angle on the PET film, h, against surfactant con-
centration, C

Figure 3 Change in removal efficiency of stearic acid from the PET film in a Figure 4 Effect of surfactant concentration on removal efficiency of stearic
1.4 · 10–4 mol/dm3 AE (EO10) solution with wash time acid from the PET film

116 Tenside Surf. Det. 51 (2014) 2


Yu Nagai et al.: Comparison of cleaning power between alcohol ethoxylates or methyl ester ethoxylates
Tenside Surfactants Detergents downloaded from www.hanser-elibrary.com by Purdue University Library TSS on August 20, 2016

Figure 5 Typical HPLC chromatograms.


(A) Stearic acid standard, (B) Sample extracted from
AE (EO10) micelles, (C) Sample extracted from AE
(EO20) micelles

retention time *8 min obtained with reference stearic acid


solution was not observed for the sample extracted from AE
(EO10) and AE (EO20) micelles. This indicated that the so-
lubilization of stearic acid into the nonionic surfactant mi-
celles did not take place in the present system.
In the present system, the solid stearic acid can be de-
tached directly from the PET film. In this case, the soil re-
For personal use only.

moval is equivalent to the penetration of the surfactant solu-


tion between stearic acid and the PET film in the contact
zone [21, 22]. Above cmc, free surfactant molecules can be
supplied from the micelles and adsorbed onto stearic acid
and the PET film surfaces successively during the cleaning
process. For EO 10 nonionic surfactants with less water sol-
ubility, it is considered that the adsorption is rapid and favor-
able for removing stearic acid.
The soil removal efficiency in Fig. 4 was plotted against
surface tension (Fig. 1) and contact angle (Fig. 2). The re-
sults are demonstrated in Fig. 6 (the upper and the middle).
The experimental results obtained for different detergents
were plotted on nearly the same curve. Such good relations
suggest that the liquid penetration between stearic acid and
the PET film is a dominant factor in the soil removal in the
present system. Because surface tension and contact angle
are not independent, the detergency was plotted again as s
function of the wetting force, c cos h, corresponding to the
driving force of the penetration (the lower in Fig. 6).
Although the correlation was not sufficient due to the devia-
tion of the results for EO15 nonionics, the detergency ex-
pectedly increased with increasing wetting force,

4 Conclusions

The critical micelle concentration, cmc, of the nonionic AE


and MEE was expectedly at least one order of magnitude
smaller than that of the anionic AS. In the case of nonionic
surfactants with the same EO chain length, the surface ex-
cess concentration was larger and therefore the effective oc-
cupied area was smaller for AE with relatively linear molecu-
lar structure than for MEE with bent and curved molecular
structure. The effective occupied area expectedly increased
with increasing EO chain length in both cases of AE and
MEE. The contact angle of the surfactant solution on the
PET film decreased with increasing concentration and re- Figure 6 Relation between removal efficiency and surface tension, c, con-
mained almost constant above cmc. The surface tension-low- tact angle on the PET film, h, and wetting force, c-cosh

Tenside Surf. Det. 51 (2014) 2 117


Yu Nagai et al.: Comparison of cleaning power between alcohol ethoxylates or methyl ester ethoxylates

ering and wettability–enhancing abilities of surfactant de- 18. Rosen, M. J., Cohen A. W., Dahanayake, M. and Hua, X. Y.: J. Phys. Chem.
86 (1982) 541. DOI:10.1021/j100393a025
creased with increasing EO chain length in both cases of 19. Miller, C. A. and Raney, K.H.: Colloids Surf. A 74 (1993) 169.
AE and MEE. DOI:10.1016/0927-7757(93)80263-E
The removal of stearic acid from the PET film was pro- 20. Ishii, S.: in The Chemical Handbook I, M. Ohki, editor, Maruzen, Tokyo 1993,
326.
moted by the addition of the surfactants, depending on EO 21. Gotoh, K.: J. Surf. Det. 8 (2005) 305. DOI:10.1007/s11743-005-0360-4
chain length (EO10 > EO15 > EO20) for the nonionic surfac- 22. Gotoh, K., Tagawa, Y. and Tabata, I.: J. Oleo Sci. 57 (2008) 495.
tants. The removal efficiency was almost constant above cmc DOI:10.5650/jos.57.495
for anionic surfactant AS and EO15 and EO20 nonionic sur- Received: 30. 10. 2013
factants, whereas further increase in the soil removal above Revised: 16. 12. 2013
cmc was observed for EO10 nonionic surfactants. The plots
of the removal efficiency against the surface tension and the Bibliography
contact angle showed good relation, indicating that the liq-
uid penetration between stearic acid and the PET film is a DOI 10.3139/113.110290
Tenside Surf. Det.
dominant factor in the soil removal in the present system. 51 (2014) 2; page 113 – 118
The detergency evaluation in anionic-nonionic mixed surfac- ª Carl Hanser Verlag GmbH & Co. KG
Tenside Surfactants Detergents downloaded from www.hanser-elibrary.com by Purdue University Library TSS on August 20, 2016

ISSN 0932-3414
tant systems will be concerned in the future.
y Correspondence address
Acknowledgements
Keiko Gotoh
The authors would like to express their gratitude to Dr. Kakeha- Faculty of Human Life and Environment
shi and Mr. Tokai, Osaka Municipal Technical Research Insti- Nara Women’s University
Kita-uoya-nishi-machi
tute, for HPLC analysis and useful discussion and Lion Corpora- Nara 630-8506
tion for providing nonionic surfactants. Gratitude is expressed to Japan
E-Mail: k-gotoh@cc.nara-wu.ac.jp
the Ministry of Education, Sports, Culture, Science and Technol-
ogy, Japan for a Grant-in-Aid for Scientific Research to carry out
this work. The authors of this paper
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118 Tenside Surf. Det. 51 (2014) 2