Journal of Dispersion Science and Technology

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

Synthesis of Surfactants From Alkali Lignin for

Enhanced Oil Recovery

Shuyan Chen, Shicheng Shen, Jie Mi, Yujie Zhou, Gehua Wang, Xiang Yan &
Jianan Zhang

To cite this article: Shuyan Chen, Shicheng Shen, Jie Mi, Yujie Zhou, Gehua Wang, Xiang Yan
& Jianan Zhang (2015): Synthesis of Surfactants From Alkali Lignin for Enhanced Oil Recovery,
Journal of Dispersion Science and Technology, DOI: 10.1080/01932691.2015.1118703

To link to this article: http://dx.doi.org/10.1080/01932691.2015.1118703

Accepted author version posted online: 30

Nov 2015.

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 Synthesis of Surfactants from Alkali Lignin for Enhanced Oil Recovery

Shuyan Chen1, Shicheng Shen2, Jie Mi2, Yujie Zhou1, Gehua Wang1, Xiang Yan1 and
Jianan Zhang1,

1
Tsinghua University, Beijing, China, 2Taiyuan University of Technology, Taiyuan, China

Corresponding author. E-mail: zhangja@tsinghua.edu.cn

Abstract
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With the cheap and abundant resource of alkali lignin as feedstock, surfactants for

enhanced oil recovery were synthesized by amination and alkylation reaction of

lignosulfonate. The effects of amination conditions, including the ratio of raw materials,

amination reagent, temperature, and reaction time, on nitrogen contents and surface

tension of the surfactants were investigated. The results showed that ethylenediamine was

more suitable for amination, and the molar ratio of alkali lignin, ethylenediamine, and

formaldehyde was 1:2:1.5 at 80 ºC for 5 h. The structure of synthesized products was

characterised by Fourier transform infrared spectrometry. The HLB value of synthesized

product was 10. The interfacial tension between Daqing crude oil and synthetic water

could be decreased to 10-2 mN/m with synthesized surfactant and NaOH at 45 ºC.

Moreover, the effects of molecular weight of surfactants on interfacial tension were also

studied. The synthesized surfactant (Mw >10,000) showed a better interfacial activity on

Daqing crude oil.

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KEYWORDS: alkali lignin; amination; surfactant; surface tension; interfacial tension

1. INTRODUCTION

Due to the world’s increasing need for petroleum, enhanced oil recovery (EOR) has

become an important research direction in oil exploration. Surfactant flooding [1] is an

effective EOR method. Surfactants for oil recovery have parental functional structures

[2], which can decrease the oil/water interfacial tension (IFT) and remove the residual oil

in reservoir; therefore, the efficiency of oil recovery could be improved [3][4]. Common

surfactants for oil recovery include petroleum sulfonate, alkyl benzene sulfonate, and

petroleum carboxylate [5][6], but production costs are usually high. So the development

of high efficiency and low cost oil-displacing surfactants is an important task for EOR

operation in oil fields of China.

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 With a low cost and abundant resource, the molecular structure of alkali lignin contains a

variety of reactive functional groups [7][8], such as phenolic hydroxyl groups, alcoholic

hydroxyl groups, carbonyl groups, and carboxyl groups, which could be used to

synthesize oil-displacing and other surfactants [9][10][11]. The interfacial performance of

alkali lignin would be affected by the molecular weight and the number of functional

groups in the molecules [12]. Morrow [13] studied the chemical modification of alkali

lignin, and the IFT of the products reached 0.1 mN/m. Zhang et al. [14] investigated the
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modification of alkali lignin, and the minimum IFT could be reduced to 0.2~0.3 mN/m

when used with alkali. However, the hydrophilic and hydrophobic ability of conventional

lignosulfonate is poor and could not meet the needs of surfactant flooding for EOR.

Accordingly, the molecular modification should be made to increase the hydrophilic and

hydrophobic properties of lignosulfonate.

In this paper, a new cost effective high performance surfactant, LS-A1, was successfully

synthesized. The alkali lignin was firstly pretreated with hydrogen peroxide (H2O2) for

oxidation [15]. Then, oxidized alkali lignin was reacted with sodium sulfite at high

temperature to achieve lignosulfonate. Last, target surfactant LS-A1 was prepared via

amination [16] and alkylation. The effects of amination conditions, including reaction

ratio of raw materials, amination reagent, temperature, and reaction time on nitrogen

content and surface tension of the surfactants were investigated. Interfacial behavior of

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 LS-A1 was also conducted to offer guidance of the formula screening and application of

lignosulfonate surfactants in EOR field.

2. EXPERIMENTAL

2.1 Materials

Alkali lignin was purchased from paper mills in Shandong Province, China. Prior to

chemical reaction, alkali lignin was purified by acid precipitation. Hydrogen peroxide
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and sodium sulfite, which were analytical pure grade, were obtained from Beijing

Chemical Reagent Co., China. Analytical pure grade ethylenediamine,

diethylenetriamine, triethylene, formaldehyde, and bromohexadecane, were purchased

from Sinopharm Chemical Reagent Co., China.

2.2 Measurements

2.2.1. Modifications of Alkali Lignin

The feedstock for amination was oxidized, sulfonated alkali lignin. Alkali lignin was first

dissolved in water in a three-necked round-bottom flask, H2O2 was then added and kept

at 70 ºC for 30 minutes. After that, the mixture was cooled down to room temperature and

pH was adjusted to 3 after adding sulfuric acid solution. Then the aqueous phase was

removed by reducing pressure with Buchner funnel and oxidized alkali lignin was

obtained. The oxidized, sulfonated alkali lignin was synthesized based on sulfonation

methods from oxidized alkali lignin and sodium sulfite at 180 ºC for 30 minutes. After
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 the sulfonation, lignin was then subjected to amination under different conditions. Last,

the target surfactant LS-A1 was prepared based on alkylation method from lignin amine

with bromohexadecane at 80 ºC for 6 hours.

2.2.2 Molecular Weight Separation of Surfactant LS-A1

A stainless steel membrane was used in this experiment; the membrane pore size was 0.1

µm, which could intercept molecules of relative molecular weight of 10,000. The
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surfactant LS-A1 was first dissolved in water then added to feed tank; then the solution

was filtered through the stainless steel membrane filter using the pump. The leachate was

collected, and the concentrated solution was returned to the feed tank.

2.2.3 Measure of Lignin Nitrogen Content

Nitrogen content of the lignin was determined using a KDN-04A azotometer (CANY,

China) with reference to the Kjeldahl method.

2.2.4 Characterization of The Synthesized Products

The structure of synthesized products was characterized by Fourier transform infrared

spectroscopy (FTIR) (FTS-470, USA) with a resolution of 4 cm-1 using the regular KBr

compression method in the range of 4000 to 400 cm-1.

2.2.5 The Hydrophile-Lipophile Balance (HLB) Measurement

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 The emulsification method was used to measure the HLB value of LS-A1, when the HLB

value of surfactants and the HLB value of oil phase medium was the same, the stability of

generated emulsion was the best.

The cottonseed oil and turpentine were used to configure a certain HLB value of 7, 8, 9,

10, 11, 12, 13, 14, 15 and 16 of the standard oil samples, respectively. Then 20 mL

0.5wt% LS-A1 was added into the above all sorts of different HLB value of 20 mL
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standard oil samples, the solution was shaken intensively and then equilibrated until two

independent layers were separated. The oil/water separation time was recorded, the HLB

value of standard oil corresponding to emulsion with the best emulsifying effect is the

one of sample to be tested.

2.2.6 Surface Tension Measurement

Surface tension tests were conducted on a dynamic surface tensiometer QBZY-2 (CANY,

China) under room temperature by Wilhelmy Type.

2.2.7 IFT Measurement

The IFT tests were conducted on SVT20N spinning drop IFT apparatus (Eastern-

Dataphy, China). Crude oil and brine from the Daqing oil field in China were used. The

total salinity of brine was 5600 mg/L. The measurements were conducted under the

reservoir’s temperature, 45.0 C. The IFT had been recorded over 30 minutes.
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 3. RESULTS AND DISCUSSION

3.1 Optimum Amination Reaction Conditions of Lignin Amine

The introduction of organic polyamine through the amination reaction of alkali lignin

could increase the nitrogen content in lignin amine. So the change of nitrogen content

before and after the amination reaction was employed as a reference to examine the
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influence of reaction conditions on the amination reaction. The relationship between

nitrogen content and reaction conditions for amination were investigated. The amination

reagent, the reaction temperature, the reaction time and the reaction ratio were chosen as

investigating factors. The results are listed in Table 1 and Table 2.

As shown in Table 1, no remarkable difference of ethylenediamine, diethylenetriamine

and triethylene could be assigned between the organic polyamine and nitrogen content.

Hence, ethylenediamine was found more suitable for amination considering the lower

price. In addition, the nitrogen content increased rapidly when the amination time was

less than 5 h, while the nitrogen content did not differ when amination time exceeded 5 h.

Nitrogen content was 3.50% when amination time was 5 h. The increase of nitrogen

content was not obvious when the temperature was higher than 70 ºC, and the nitrogen

content was 3.60% when the amination temperature was 80 ºC. The effects of reaction

ratio of the amination reagent were also shown in Table 2. In this experiment, the ratio of

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 amination reagents was regulated by changing the molar amount of ethylenediamine and

formaldehyde while fixing the molar amount of alkali lignin. Nitrogen contents increased

when increasing the dosage of ethylenediamine or formaldehyde. The nitrogen content

reached 3.54% when the molar ratio of alkali lignin, ethylenediamine and formaldehyde

was 1:2:1.5.

To deeply understand the influence of amination reaction conditions on the synthesized

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products, the lignin amines prepared under the above conditions were further modified by

alkylation reaction for surfactants preparation. The surface tension of surfactants LS-A1

was measured by dynamic surface tensiometer QBZY-2. The results are shown in Fig. 1

to Fig. 4.

As seen in Fig. 1, the surface tension value changed little in the experimental amination

time (from 4 h to 7 h), but the nitrogen content was much higher when the amination time

exceeded 4 h (Table 1). The maximal nitrogen content could be assigned at 5 h. So the

amination time of 5 h could be affirmed as the best reaction time of all given

experimental times.

The influences of reaction temperature on surface tension of surfactants LS-A1 are shown

in Fig. 2. The reaction temperature had a remarkable influence on the surface tension of

surfactants LS-A1. The surface tension value of surfactants synthesized at a high

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 amination temperature (80 to 90 ºC) was lower than that of surfactants synthesized at low

temperatures (60 to 70 ºC), which mainly indicated that effective active matter content of

synthetic surfactants was increased at the higher temperature (80 to 90 ºC). When

amination temperature was 80 ºC, the surface tension reached 26.0 mN/m, and the

nitrogen content was 3.60%, so the amination temperature of 80 ºC was the most suitable

reaction temperature in this experiment.

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Figure 3 indicates the effects of molar ratio of amine reagents on the surface tension of

surfactants LS-A1. The surface tension of surfactants LS-A1 decreased as the dosage of

ethylenediamine and formaldehyde increased. When the molar ratio of alkali lignin,

ethylenediamine, and formaldehyde was 1:2:1.5, further increasing the dosage of

formaldehyde would not result in the decrease of surface tension of the surfactants. The

results were in accordance with the aforementioned nitrogen contents (Table 2). The

optimized molar ratio of alkali lignin, ethylenediamine and formaldehyde for amination

reaction was 1:2:1.5.

In addition, the influence of amination reagent type on the surface tension of surfactants

LS-A1 was also studied (Fig. 4). For ethylenediamine, diethylenetriamine, and

triethylene, there was less influence on surface tension of surfactant LS-A1. Therefore

ethylenediamine was more suitable for amination considering the lower price and

nitrogen content tests. The experiments showed that all of the factors could influence the
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 surfactant performance. The effects of the reaction time and molar ratio of amine reagents

were most obvious. So the optimum conditions for amination reaction with high nitrogen

content were as follows: the amination reagent was ethylenediamine; the amination time

was 5 h; the amination temperature was 80 ºC; and ratio of alkali lignin:

ethylenediamine:formaldehyde = 1:2:1.5 (molar ratio).

3.2 FTIR Characterization of The Synthesized Products

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Figure 5 exhibits the FTIR spectra of oxidized lignin, lignosulfonate, lignin amine, and

the target surfactant LS-A1.

The bands beyond 1724 cm-1 corresponded to C=O groups (unconjugation with aromatic

ring). The peaks at 1600 cm-1, 1516 cm-1, and 1423 cm-1 indicated the presence of

aromatic ring in the materials [17][18]. The absorption band at these regions was

relatively low, which could be attributed to the degradation of the aromatic ring after

oxidation. The peaks at 1395 cm-1 and 1464 cm-1 revealed the presence of methylene

groups. The FTIR spectra of the materials indicated the presence of C-O bonding and C-

C bonding by the peaks between 1300 cm-1 and 1000 cm-1, and they were different in

four spectra.

Compared with oxidized lignin, the peaks between 1300 cm-1 and 1000 cm-1 were

broadened in lignosulfonate (spectrum 2), lignin amine (spectrum 3), and the target
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 surfactant LS-A1 (spectrum 4), which could be attributed to the increase of signals of

S=O and C-N stretching vibrations after sulfonation and amination, respectively, and the

peaks would be overlapped with the aforementioned peaks of C-O and C-C. In addition,

the presence of C-H by the peaks at 2924 cm-1 and 2852 cm-1 (spectrum 4) and the peak

of C-H deformations at 1466 cm-1 was also increased, which indicated that carbon chain

(lipophilic group) was introduced to lignin molecule.

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3.3 HLB Measurement

The hydrophilic or hydrophobic degree of a surfactant can be described quantitatively by

the HLB theory. The interface properties for a surfactant have a close connection with

HLB value [19][20][21]. As indicated in Fig. 6, the HLB value of surfactant LS-A1 was

10. Even though the oleophilic linear alkyl group was introduced into the product, the

hydrophilic amino group and sulfonic group were also introduced into the product,

therefore the HLB value of surfactant LS-A1 was 10.

3.4 IFT Measurements

The IFT of oil/water interface is a very important parameter to liberate residual oil. The

lower the IFT of the oil/water interface, the higher the oil recovery efficiency. The effect

of alkali concentration on IFT of LS-A1/crude oil was investigated first. The

concentration of NaOH varied from 0 to 1.2 wt% and the concentration of LS-A1 was 0.4

wt%. The results are shown in Fig. 7.

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 As indicated in Fig. 7, the surfactant LS-A1 could reduce IFT in the presence of NaOH

compared to that of the surfactant without NaOH. The IFT of LS-A1/crude oil could

reach 10-2 mN/m level when the concentration of NaOH was 1.2 wt%; although the

instantaneous IFT of LS-A1/crude oil was not the lowest, it was still much more stable

and lower than those used with other alkali concentrations. Alkali was beneficial to lower

the interfacial tension, and when a suitable concentration of alkali was used with
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surfactants, the synergetic effects could further decrease the interfacial tension [22]. The

results were similar to those from Jiao et al. [23], where the alkali lignin was used as

feedstock and the IFT of the surfactants obtained via amination, acylaction and

sulfonation was 10-2 mN/ m when dissolved with NaOH. The effect of surfactant LS-A1

concentration on the IFT is shown in Fig. 8. The concentration of surfactant LS-A1

varied from 0.2 wt% to 0.8 wt% and the concentration of NaOH was 1.0 wt%. The

surfactant LS-A1 concentration had little influence on the IFT when the NaOH

concentration was fixed. When the concentration of the surfactant LS-A1 was 0.4 wt%,

as a whole the IFT was lower than that of other surfactant LS-A1 concentration. The

results again indicated that the IFT reducing ability of surfactant was associated with the

concentration of alkali and surfactant.

An oil-displacing surfactant should be well able to reduce the IFT between oil and water.

The relative molecular weight of the surfactant is one of the most critical factors which
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 influence the interfacial activity. In order to investigate the influence of the relative

molecular weight of surfactant LS-A1 on the IFT of water/oil, the surfactant LS-A1 was

cut based on relative molecular weight. The IFT of different relative molecular weights of

surfactants LS-A1 was shown in Fig. 9. According to the Gibbs adsorption theory, the

more the effective absorption amount of surfactants at the oil/water interface, the lower

the IFT will be [24]. The lowest IFT was achieved for the surfactant LS-A1 (Mw >

10,000) solution and crude oil mixture with 1.0 wt% NaOH, which indicated that the
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aggregation of different relative molecular weight surfactants in solution could be

disturbed by the interaction between NaOH and surfactant molecules.

The IFT curves of surfactant LS-A1 (Mw>10,000) and crude oil mixture with the

concentration of NaOH are shown in Fig. 10. The surfactant LS-A1 (Mw>10,000) could

decrease the IFT with the range of NaOH concentration from 0.2 wt% to 1.0 wt%. It was

similar to that of unsegregated surfactant. Particularly, the IFT between surfactant LS-A1

(Mw>10,000) and crude oil was lower than that of unsegregated surfactant with the same

concentration of NaOH, which indicated that the surfactant LS-A1 (Mw>10,000) showed

better interfacial activities on Daqing crude oil.

4. CONCLUSIONS

The test results of nitrogen content after amination, and the surface tension for the

synthesized surfactants LS-A1 showed that the optimized conditions for amination were
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 as follows: n (alkali lignin) : n (ethylenediamine): n ( formaldehyde) = 1:2:1.5 (molar

ratio); the reaction temperature of 80 °C and the reaction process last for 5 h. After

further alkylation of the lignin amine, the target surfactant LS-A1 was successfully

synthesized from alkali lignin.

The oxidized lignin, lignosulfonate, lignin amine, and the target surfactant LS-A1 were

qualitatively analyzed by FTIR. There was an increase in the characteristic stretching

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peak of C=O in the lignin oxidized by H2O2. The bands of S=O and C-N overlapped with

the bands of C-O and C-C between 1300 cm-1 and 1000 cm-1 after sulfonation and

amination, respectively. In addition, the increase of the bands of C-H clearly indicated the

introduction of the long carbon chain.

The IFT between Daqing crude oil and brine could be decreased to 10-2 mN/m level with

the surfactant LS-A1 and NaOH at 45 ºC. Compared with the surfactant concentration,

that of alkali played an important role in reducing the IFT. Particularly, the surfactant LS-

A1 (Mw > 10,000) showed the better interfacial activities on Daqing crude oil compared

with unsegregated surfactant.

ACKNOWLEDGMENTS

The authors are grateful for the financial support of the National High Technology

Research and Development Program (863 Program) of China grant (No.

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 2014BAD02B00), the Tsinghua University Initiative Scientific Research Program (No.

2012THZ02289) and National Energy Administration (No. 20131448926).

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 Table 1 Effects of amination reagent, reaction temperature and reaction time on nitrogen

content of lignin amine

Type of amination Nitrogen Amination Nitrogen Amination Nitrogen

reagent content time (h) content temperature content

(%) (%) (°C) (%)

Ethylenediamine 2.15 4 2.26 60 3.24

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Diethylenetriamine 2.20 5 3.50 70 3.51

Triethylene 2.27 6 3.46 80 3.60

7 3.38 90 3.55

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 Table 2 Effects of the ratio of amination reagents on nitrogen content of lignin amine

n (alkali lignin) : n 1:0.5:1 1:1:1 1:2:1 1:2:1.5 1:2:2

(ethylenediamine) : n

(formaldehyde)

Nitrogen content (%) 1.55 2.04 3.05 3.54 3.52

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 Fig. 1 Effect of amination time on the surface tension of surfactants LS-A1
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 Fig. 2 Effect of amination temperature on the surface tension of surfactants LS-A1
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 Fig. 3 Effect of molar ratio of the amination reagents on the surface tension of surfactants

LS-A1
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 Fig. 4 Effect of amination reagent type on the surface tension of surfactants LS-A1
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 Fig. 5 FTIR spectra of the oxidized lignin (1), lignosulfonate (2), lignin amine (3) and the

target surfactant LS-A1 (4)

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Fig. 6 Standard oil of HLB value

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 Fig. 7 Effect of alkali concentration on the interfacial tension of the surfactants LS-A1
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 Fig. 8 Interfacial tension of different concentration surfactant LS-A1 with NaOH solution
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 Fig. 9 Interfacial tension of different relative molecular weight surfactant LS-A1 with

NaOH solution
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 Fig. 10 Effect of alkali concentration on the interfacial tension of the surfactant LS-A1

(Mw>10000)
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