Journal of Oleo Science

Copyright ©2016 by Japan Oil Chemists’ Society

doi : 10.5650/jos.ess15276
J. Oleo Sci. 65, (8) 663-670 (2016)

Synthesis and Performance Properties of Cationic

Fabric Softeners Derived from Free Fatty Acid of
Tallow Fat
Mithun G. Mondal and Amit Prabhakar Pratap＊
Department of Oils, Oleochemicals and Surfactant Technology, Institute of Chemical Technology, Matunga, Mumbai, Maharashtra, INDIA

Abstract: Esterquat cationic softener is basically the class of surface active quaternary ammonium
compounds. Esterquat compounds were synthesized and their surface behavior, antibacterial activity and
Textile softening properties were investigated. Easily found cheap material was used to synthesize cationic
fabric softeners. This fabric softener will be a good for commercially and industrially important because
their emulsify activity, rewettability dispersing power and softness. Free fatty acids were derived from
tallow oil and were treated with triethanolamine and mono-ethanolamine at 140℃. This diester was
quaternaries with dimethyl sulphate and benzyl chloride. The synthesized esterquat compounds were
characterized by its cationic content, 1H NMR and FT-IR analysis. In addition to the cationic content,
surface tension, CMC (critical micelle concentration), rewettability, fabric softening, emulsification and
dispersing power were determined as their surface-active properties. The fabric softening activity of
esterquat and esteramide prepared from DMS was better softening activity of fabrics compared to untreated
cotton and polyester fabrics cloth. The presented result shows that the esterquat made from BCl exhibit the
best dispersing power. The esterquat made from DMS both in TEA and MEA shows good rewettability was
determined.

Key words: ‌cationic surfactant, esterification, quaternization, CMC, fabric softening, rewettability, emulsification,
dispersing power, antibacterial activity

1 Introduction between fibbers and imparts a soft, fluffy feel to the

Esterquat cationic surfactant is the main constituent of a fabric7）.
fabric softener composition. This new type of fabric soften- In this paper, we report on the synthesis of cationic sur-
ing agent combines a good environmental profile with the factant derived from esterification of tri and mono-ethanol-
structural features required for an effective fabric condi- amine with free fatty acid of tallow oils. This fatty ester
tioner1, 2）. Esterquat cationic surfactant is one of the biode- reacts with an alkylating agent like dimethyl sulfate and
gradable fabric softener due to the presence of ester benzyl chloride to form corresponding quaternary com-
linkage3）. Specialty of cationic surfactant is environmental pound8）. The obtained product in each case was character-
friendly, non toxic and biodegradable properties 4）. Quats ized by its cationic content and structure was confirmed by
have been proven to be useful in variety of application, in- 1H NMR and FT-IR analysis. Each surfactant surface active
cluding the following as fabric conditioner, antistatic agent, property can be measure in a variety of ways and the
biocides, emulsifiers in cosmetics, antibacterial agent, cor- method of choice often depends on the characteristics of
rosion inhibiters and foam dispersant5）. Esterquats are im- the substance to be analysis. The most frequently deter-
portant classes of surfactants that have distinctive qualities mined properties probably are surface tension and critical
that make them attractive for exploration. Esterquats micelle concentration.
contain a hydrophilic polar“head”–OH group, and a hy-
drophobic alkyl chain“tail”6）. They are absorbed on the
surface of fabric with their hydrophobic group oriented
away from the fabric. Surfactant reduces the friction

＊
Correspondence to: Amit Prabhakar Pratap, Department of Oils, Oleochemicals and Surfactant Technology, Institute of Chemical
Technology, Matunga, Mumbai, Maharashtra, INDIA
E-mail: [email protected]
Accepted April 9, 2016 (received for review November 30, 2015)
Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 online
http://www.jstage.jst.go.jp/browse/jos/ http://mc.manusriptcentral.com/jjocs

663
 M. G. Mondal and A. P. Pratap

2 Materials and method 1）was obtained from fatty acid with triethanolamine. The
2.1 Materials for Synthesis of Esteramide Quates diester was prepared by a triethanolamine with fatty acid,
The reagent used in synthesis of diester and esterquat followed by reaction with an alkylation agent to the corre-
were purchased from Sigma Aldrich Pvt. Ltd, India while sponding quaternary. In the presence of a catalyst ortho-
toluene, diethyl ether, hexane and various other solvents phosphoric acid the（2 mole）of fatty acid and（1 mole）of
used were purchased from Thomas baker’ s Pvt. Ltd. triethanolamine was heated up to temperature 160-170℃
Mumbai, India. to obtain high conversion and water removal is enhanced
Fabrics for evaluation of softening and rewettability, i.e. by striping with an inert gas. The reaction times vary from
100％ cotton and 100％ polyester were obtained from the 8-10 hours and the reaction was monitor by acid values.
market. The acid value was checked after half an hour. The reac-
tion was continued until acid value reached 6.0.Similarly,
2.2 Experimental the reaction for the preparation of ester amide of mono-
2.2.1 Synthesis of diester from tallow free fatty acid ethanolamine with free fatty acid of tallow fat.
The reaction for the synthesis of diester esterquat （Fig.

Fig. 1 Synthesis of esteramide and esterquats.

664
J. Oleo Sci. 65, (8) 663-670 (2016)
 Synthesis and Performance Properties of Cationic Fabric Softeners

2.2.2 Quaternerization of Esterquats Where,

The free fatty acid of diester and esteramide is reacted M1＝Molarity of esterquat
with an alkylation agent like dimethyl sulphate, benzyl M2＝Molarity of sodium lauryl sulphate
chloride, to obtained corresponding quaternary ammonium V1＝Used volume for esterquat
compound（Fig. 1）. For this 1 mole of di-ester of tri-etha- M XmolweightofesterquatX 100
Cationic content＝ 1
nolamine was dissolve in petroleum ether in 250 mL of weightofsampleX4
round bottom flask. Thermometer was inserted in one neck
of flask and condenser was fitted on the other neck. When 3.2 Determination of cmc, γcmc
the di-ester was completely dissolved in it, then 1.5 mole of The surface tensions of aqueous of the esterquats were
alkylating agent was added drop by drop with constant measured with a Kruss K11 tension tenstiometer with the
starring for 2 hours at 65‒70℃. Esterquats were trans- help of a Wilhelmy plate made up of platinum. Measure-
ferred to a beaker and the petroleum ether was evaporated ment were taken at 25±1℃. The surfactant solution was
on water bath until a viscous compound was obtained. added to water in a thermos tatted glass vessel by using a
Similarly the esterquat of monoethanolamine was pre- micro syring. CMC and surface tension at CMC were deter-
pared by using alkylating agent like dimethyl sulphate, mined from the breakpoint of the surface tension of their
benzyl chloride, to obtained corresponding quaternary am- aqueous solution versus concentration.
monium compound （Fig. 1）.
3.3 Emulsibilty
The emulsibilty of the synthesized cationic surfactant
was determined using 10 ml of 1％ aqueous solution of sur-
3 Characterization of esterquat and Esteramide Quat factants and 5 mL of toluene at 40℃. The mixed liquid was
3.1 Determination of Cationic Content9, 10）: stirred by homogenizer for 1 min and the emulsion was
The cationic content of esteramide and esterquats was formed. The emulsion was poured into a measuring cylin-
determined using the method describe in BIS: 4955 （1978） der, and the time was recorded when as the time of separa-
p 8. tion of water（9 mL）from the emulsion layer11）.
Reagent
1．Chloroform 3.4 Dispersing power
2．0.004 M Sodium Lauryl Sulphate Solution Dispersing power of the prepared esterquats was deter-
1.464 g of sodium Lauryl sulphate was dissolve in mined using TiO2 and 1％ surfactant solution. The surfac-
1000 ml of distilled water to make 0.004 M solution. tant solution with TiO2 were shaken and allowed to stand.
3．0.003％ Methylene Blue Solution Dispersing power was carried out by looking at the height
0.003 g of Methylene blue, 30 g of sodium sulphate and cloudiness of surfactant solution and recorded the
and 4.1 mL of concentrated sulphuric acid were scores12）.
taken in distilled water and diluted to 1000 ml with
distilled water. 3.5 Softening power
4．0.004 M Esterquat Solution A‘feel’test panel to determine the softeners was
Adequate quantity of esterquat was weighed and dis- applied, based on the panel feel test13, 14）. The treated and
solved in 20-30 mL of ethanol and made the volume non-treated, cloth were to the trained panelist with the re-
up to 250 mL distilled water. quirement to judge which cloth of the pair is softer. The
Procedure softening rating of different substrate decided by average
10 mL of standard cationic surfactant solution（ester- grade obtained from panelist, better softer has higher
quats, esteramide）was taken in 250 mL stopper flask and grade given in Table 6.
add 15 mL chloroform and 25 mL of methylene blue solu-
tion to the cylinder and shake well. After gentle shaking, 3.6 Rewettability
flask was allowed to stand until the two layer separated. The dye wick-up method15） was used to measuring the
The organic layer was blue colored. It was then titrated rewet of treated fabric with the investigated softening for-
against 0.004 M solution of sodium lauryl sulphate. mulation16）. Initially, the standard fabric were treated the
Towards the end point the colour would start migrating to same way as in above-mentioned softening method. Then
the aqueous layer. The reading was noted down when the the fabric were hung vertically and dipped in a 0.2 wt％
same colour intensity in both the phase was observed. telon blue RR acid dye solution, where the immersion
Cationic content was measured as follows: depth was 2 cm. A stopwatch was started as soon as the
strip was fabric strip was dipped. The distance of dye sepa-
Molarity of esterquat M1＝10M2 / V1 ration was measured in centimeter at 5 min, as the height
of wetted cationic treated fabrics. Table 5 shows rewetta-
665
J. Oleo Sci. 65, (8) 663-670 (2016)
 M. G. Mondal and A. P. Pratap

bility data of different treated fabric with different surfac- mixture at 150℃. In the presence of catalyst Orthophos-
tant solution. phoric acid was found yield for this reaction. The lowest
acid value（5.5）of diester was obtained at 170℃ with Or-
3.7 Instrumental Analysis thophosphoric acid as a catalyst. The diester derived from
The structures of compounds were determined by means free fatty acid gave a maximum yield was carried out at
of spectral analysis: 1H NMR and FT-IR. FT-IR spectra 170℃. The reaction was controlled by monitoring the acid
were obtained by using a model Miracle 10.DRS plate of value during the synthesis.
the sample was subjected to analysis with 30 scan. NMR
spectra were recorded with a Bruker avance DRX-500 in 4.3 Synthesis of Esterquats
CDCl3 solution. Table 2 shows the yield percentage yields by weight and
cationic content of different di-esterquats, prepared by
quaternization of diester and ester amide by DMS and
Benzyl chloride. The quaternization was carried out at a
4 Results and Discussion 70-80℃ for 2 hours and cationic matter for each product
4.1 Characteristics of Experimental Fatty Acids was determined. The result shows that quaternization of
The acid value, saponification value, appearance and diester for 2 hours using 1:1.5 molar ratio of diester to dif-
melting point of free fatty acid of tallow are in Table 1. The ferent halide group give better yield of esterquat. Quater-
acid value determined was 174.03. The saponification value nization time also had an important role in the cationic
and melting point were found to be in normal range as ex- content of esterquats. Increasing the duration of quater-
pected. nization did not increase the cationic content. The solubili-
ty test indicates that esterquat was soluble in both cold
4.2 Synthesis of Diester and warm water. The reason is that esteramide and ester-
Fatty esters are generally prepared by the reaction of an quats surfactant molecule present polar alcoholic group.
acid with a different alcohol like triethanolamine and mono Because polar group increasing solubility due to hydrogen
ethanolamine. Cationic surfactant constitutes an important bonding. The O-H bond is not only polar but is also able to
class of fabric softener. The aim of research was to synthe- form hydrogen bond with water molecule as well as each
size better surfactant from easily available chiefly fatty acid other.
like tallow, which should be better quality and yield of
product. The esterquat was prepared by two steps, the 4.4 1H NMR
product obtained from the first step, which involved ester Spectral data of Esteramide and Esterquats surfactant
formation from free fatty acid and alcoholic amine like are as follow:
mono and triethanolamine. In etherification reaction the 1）6a- Esteramide of dimethyl sulphate
lowest acid value of product was obtained. The acid value 1H NMR（500 MHz CDCl3）: δ 0.86-1.99［99 H, m,（-CH2-
of condensate product（Diester formation）reduces rapidly （CH2）n-CH2-） Aliphatic chain］; 2.66-2.33［8 H, d t,（-CH2-C
because water of condensation being removed from ＝O, -N-CH2-CH2-）］; 3.64［3 H, s,（＋N-CH3 sulphate）］;
5.32［3 H, s,（-CH3SO−4） ］
Table 1 Characteristics of tallow fat. 2）6b- Esteramide of benzyl chloride
1H NMR（500 MHz CDCl3）: δ 0.87-1.25［83 H, m,（-CH2-
Characteristics Value
（CH2）n-CH2-）Aliphatic chain］; 2.01-2.0［6 H, t,（-CH2-CH2-
Saponification value 186.122 C＝O） ］; 2.37-2.33［8 H,（-CH2-C＝O） , -CH2-OH］ ; 5.33-5.36
Acid value 174.03 ［4 H, m,（-CH2-N＋ Benzyl）,（-CH2-OH）］; 7.26［5 H, m,
Melting point ＞40℃ （Aromatic C-H） ］ .
3）7c- Esterquats of dimethyl sulphate
Appearance Off-white, solid fat
1H NMR（500 MHz CDCl3）: δ 0.85-2.35［288 H, m,（-CH2-

Table 2 Reaction parameters of different quats derived from tallow fatty acid.
Diester: Cationic
Surfactant Molar Ratio Time (h) Yield (%)
Alkyl halide Content (%)
6a 4 : DMS 1:1.5 2h 71.03 90
6b 4 : BCl 1:1.5 2h 58.9 85
7c 5 : DMS 1:1.5 2h 70.0 89
7d 5 : BCl 1:1.5 2h 63.7 87

666
J. Oleo Sci. 65, (8) 663-670 (2016)
 Synthesis and Performance Properties of Cationic Fabric Softeners

（CH2）n-CH2-）Aliphatic chain］; 3.65［3 H, s,（＋N-CH3）- tion of diester was confirmed by The OH starching vibra-
sulphate）］; 4.4-4.17 （-O-CH2-CH2）
［4 H, t, 2 ］ ［10
; 5.30-5.37 tion and deformation was indicated by the peak at ∼
H, m, 2（-CH2-C＝O）, 2 （＋N-CH2-CH2-O-C＝O） ,（＋N-CH2- 3340.71 and ∼1076.28 cm−1 respectively. The C-N stretch-
CH2-OH）］; 5.79［3 H, s,（-CH3SO−4） ］. ing at ∼1068 cm−1（amide group）, C＝O stretching （amide
4）7d- Esterquats of benzyl chloride group）at ∼1641.42 cm−1, C＝O stretching （ester group）at
1H NMR（500 MHz CDCl3）: δ 0.86-2.36［80 H, m,（-CH2- 1737.86 cm−1.
（CH2）n-CH2-）Aliphatic chain］; 4.44-3.51［13 H, dt, 2（-O- Esterquats: FT-IR spectra of esterquat shows similar
CH2-CH2-N＋）,（＋N-CH2-CH2-OH）］; 5.34-5.76［5 H, m, type of peak as those in the spectra of diester and ester
（Aromatic C-H）］. amide, except for the peak of S＝O stretching（DMS group）
at ∼100.91 cm−1 and ∼707.8 cm−1 for benzene ring of（ar-
4.5 FT-IR omatic ring）. Presence of quaternary N＋ was confirmed by
Diester and esteramide: The FT-IR data obtained for the peak obtained at ∼1462.04 cm−1. Instrumental analysis
diester and ester amide is tabulated in Table 3. The forma- of diester, esteramide and esterquats is shown in Table 3

Table 3 Interpretation of IR spectrum.

Diester of Esteramide of
Esteramide 6a-b Esterquat 7c-d
Group Triethanolamine 5 Monoethanolamine
(cm−1) (cm−1)
(cm−1) 4 (cm−1)
O-H stretching 3340.71 3379.29 ∼3388.93 ∼3379.29
O-H Deformation 1076.26 1050 ∼1053.13 ∼1068.56
C=O 1737.86 ∼1739.79 ∼1639.49
C-O 1168.86 1124.5 ∼1197.79 ∼1124.5
Tertiary N 2850.79, 1566.2 2852.72 ∼2854.65 ∼2852.72
S=O 1006.84 1068.56
CH2 2918.3 2924.09 ∼2922.16 ∼2924.09
Mono substituted benzene ring 756.1 727.16, 702.09
+
Quaternary N 1456.26 1454.33
Where,
4- Esteramide of monoethanolamine, 5-Diester of triethanolamine
6a- Esteramide of dimethyl sulphate, 6b- Esteramide of benzyl chloride.
7c- Esterquats of dimethyl sulphate, 7d- Esterquats of benzyl chloride.

Fig. 2 FTIR spectrogram of esteramide quates.

667
J. Oleo Sci. 65, (8) 663-670 (2016)
 M. G. Mondal and A. P. Pratap

Fig. 3 FTIR spectrogram of esterquat.

Table 4 Surface active properties of different esterquat and esteramide quats derived from tallow fatty acid and TEA
and MEA.
Surface CMC Cationic Emulsion Dispersing power Average molar
Surfactant
Tension mN/m (mmol/L) content (%) stability (min) (TiO2) (vol. in ml) mass (g/mole)
6a 30.89 0.046 71.03 55 min 6.5 1082
6b 27.81 0.002 58.9 40 min 10 1096
7c 32.54 0.158 70.0 57 min 8 883
7d 29.00 0.246 63.7 42 min 10 897

and graphs are shown in Figs. 2 and 3. sion is reduced the interfacial tension between the phases
and forming the barrier between the phases. Hence, a sur-
4.6 Surface Tension factant, mostly termed emulsifier, is necessary for stabiliza-
After the synthesis of tallow based esterquat, we further tion. Esterquats and esteramide quates showed good emul-
investigated their surface active properties Critical micelle sion stability. Table 4 shows that emulsion stability was
concentration （CMC） values, surface tension at CMC（γcmc） different in different surfactant depends their size and al-
are summarized in Table 4. In general the critical micelle kylating agent. The experimental data a show that ester-
concentration indicate the concentration at which the sur- quat derived from DMS has best emulsion stability while
factant start to aggregate into micelles. Table 4 indicates esterquat derived from benzyl chloride has lower emulsion
that surface tension of all the esterquat good range that is stability.
below 30 mN/m. The CMC value was calculated by the
plate methods shown in Table 4. The tallow based ester- 4.8 Dispersing Power
quat and esteramide surfactant CMC value decreases or in- Increased length of the alkyl chain increases degree of
creases depend their central nitrogen atom of tri-ethanol- dispersing power. The dispersion of carbon in aliphatic hy-
amine, mono-ethanolamine and polar alkyl halide group drocarbon is raised by the addition of alkyl benzene. The
like dimethyl sulfate and benzyl chloride. Because of large benzene ring is presumably adsorbed onto the surface of
head group expected aggregate structure was spherical in the carbon and the alkyl chain length increases the stability
shape17）. of dispersion liquid. Increases in the length and alkyl group
to the benzene nucleus increases the stability of disper-
4.7 Emulsion Stability sion18）. The resulting data shown in Table 4 indicate that
Emulsification is defined suspension of liquid droplets the esterquat and esteramide quates prepared from benzyl
（dispersed phase）of a certain size within a second immis- chloride exhibit the best dispersing power in comparison
cible liquid（continuous phase）. The main action of emul- to prepared from DMS.
668
J. Oleo Sci. 65, (8) 663-670 (2016)
 Synthesis and Performance Properties of Cationic Fabric Softeners

Table 5 Result of fabric rewettability using different concentration of surfactant solutions.

Rewettinga
(cm)
Surfactant
100% Untreated Untreated
100% cotton
polyester cotton polyester
0.1 1.0 0.1 1.0 2.5 2.0
6a 4 4.1 1.2 1.3
6b 3.7 2.9 0.5 2.0
7c 4.5 5.5 5.0 3.0
7d 3.4 2.9 1.8 0.5
a
Dye migration after 5 min (in cm)

4.9 Rewettability Table 6 Comparable result of softening property of 1％

Surface activity of water is an important aspect for de- aqueous solution of esterquat13, 14）.
tergency, water proofing, dying water absorption. An im-
Surfactant 100% cotton 100% polyester
portant role of wetting agent is minimizing the both surface
tension of surfactant solution and its interfacial tension 6a ++++ +++
against the solid19）. The dye-wick method measure the 6b +++ ++
water absorbency characteristics of fabrics treated with 7c ++++ +++
softener. Better water absorbency is important for a
7d + +
treated cloth, because fabrics softener can change water
absorptivity of the treated textile. The absorbency rule the kaosoft agl85
+++++ ++++
increases the softener on a fabrics decreases its water ab- (commercial grade)
sorbency or increasing the softening activity decreases
water absorbency20）. It can show Table 5, that after test kaosoft agl85（commercial grade）fabric softener with syn-
with the investigated softeners, rewettability of all the thesized cationic surfactant. It was found that our fabric
cotton and polyester fabric sample decreasing trend. As cationic surfactant has less softening activity than kaosoft
the rewettability of treated fabrics, 100％ cotton shows agl85（commercial grade） surfactants. It was observed that
good migration than 100％ polyester. Similarly the both esterquat and esteramide preparation from DMS was better
untreated fabrics like cotton and polyester tested, it shows softening activity on fabrics than Benzyl chloride. This
that the rewettability activity poorest than treated fabrics. fabric softener will be a good for commercially and indus-
Esterquats made from DMS both TEA and MEA good re- trially important because their emulsify activity, rewettabil-
wettability was determined. ity dispersing power and softness. The presented result
shows that the esterquat made from benzyl chloride exhibit
4.10 Softening the best dispersing power. The esterquat made from DMS
The most cationic surfactant is used to improved fabrics both in TEA and MEA shows good rewettability was deter-
softeners21）. We had evaluated the softness property by mined. The fabric softening activity of esterquat and es-
panel feel test where the softness have been qualitatively teramide prepared from DMS was better softening activity
assessed and rating has been given in terms of one to five of fabrics compared to untreated cotton and polyester
（＋） symbols indicating poor to excellent softness property fabrics cloth.
subsequently. Their activity depends on the use in fatty
alkyl chain and quaternerizing group. It was observed from
Table 6 that esterquat and esteramide preparation from
DMS was better softening activity on fabrics. In both es- Acknowledgement
teramide quates and di-esterquats shows better softening The authors gratefully acknowledge the university grant
so we can use commercially fabrics softeners. commission（UGC-Green Tech.）of India for providing
special assistance program（SAP）fellows.

5 Conclusions
Free fatty acids were derived from tallow fat and react Supporting Information
with TEA and MEA at 150-160℃. It was compared with the This material is available free of charge via the Internet
669
J. Oleo Sci. 65, (8) 663-670 (2016)
 M. G. Mondal and A. P. Pratap

at http://dx.doi.org/jos.64.10.5650/jos.ess.15276 of palm fatty acid and 1（2-hydroxyetyl piperazine）

based cationic fabric softeners. Surf. Rev. Lett. 14,
1129-1134（2007）.
12）Hoffman, K. The chemistry of heterocyclic compound.
References Interscience Publishers Inc., New York, pp. 213-226
1）Mishra, S.; Tyagi, V. K. Esterquats: the novel class of （1953）.
cationic fabric softeners. J. Oleo Sci. 56, 269-276 13）Egan, R. R. Cationic surface active agents as fabric
（2007） . softeners. J. Am. Oil Chem. Soc. 55, 118-121（1978）.
2）Geng, T.; Li, Q. X. M; Jiang, Y. J.; Wang, W. Esterifica- 14）Mishra, S.; Tyagi, V. K. Synthesis and performance
tion of stearic acid with triethanolamine over zirconi- properties f cationic fabric softeners derived from dif-
um sulfate supported on SBA-15 mesoporous molecu- ferent fatty acids and 1（2-hydroxyethylpiperazine）. J.
（2011）
lar sieve. J. Surfact. Deterg. 14, 15-22 . Surfact. Deterg. 11, 167-173（2008）.
3）Guo, X. F.; Jia, L. H. Synthesis and application of cat- 15）Ginn, M. E.; Schenach, T. A.; Jungermann, E. Perfor-
ionic surfactant. Chemical Industry press, Beijing mance evaluation of selected fabric softeners. J. Am.
（2003） . Oil Chem. Soc. 42, 1084-1088（1965）.
4）Baker, J. A.; Willing, R. I.; Furlong, D. N. Sugar fatty 16）Bahmaei, M.; Badiee, F.; Kasehgari, H. Synthesis, IR,
acid ester surfactants: biodegradation pathways. J. HPLC analysis and performances of palm fatty acids
Surfact. Deterg. 3, 13-27 （2000） . and triethanolamine-based esterquats. J. Surfact. De-
5）Greek, B. F. Sales of detergent growing despite reces- terg. 14, 173-177（2011）.
sion. Hem. Eng. News 69, 25-52 （1991） . 17）Nagarajun, R. Molecular packing parameter and sur-
6）Ward, H. L. Textile softeners for home laundering. J. factant self-assembly: The neglected role of the sur-
Home Econ. 49, 122-123 （1992） . factant tail. Langmuir 18, 31-38 （2002）.
7）Mcnally. J. P.; Mccord, F. A. Cotton quality study: V: 18）Milton, J. Surfactant and Interfacial Phenomena 3rd ed.
resistance to abrasion. Text. Res. J. 30, 715-751 Rosen Surfactant Research Institute Brooklyn College
（1960） . the City University of New York（2004）.
8）Trius, A.; Hubert, M.; Bigorra, J.; Cuadrado, F.; Po- 19）Cutler, W. G.; Davis, R. C. Detergency Theory and Test
mares, J. Patent WO1991001295. Method. Surfactant Science Series, Vol. 5: Marcel
9）Bureau of Indian Standard: 548 （Part I） （1964）.
, p. 29 Dekker Inc. New York（1981）.
10）Tyagi, R.; Tyagi, V. K.; Khanna, R. K. Synthesis, char- 20）Egan, R. R. Cationic surface active agents as fabric
acterization and performance of tallow fatty acids and softeners. J. Am. Oil Chem. Soc. 55, 118-121（1978）.
triethanolamine based esterquats. J. Oleo Sci. 55, 21）Richmond, J. M. Cationic surfactant. Surfactant Sci-
337-345 （2006） . ence Series Vol. 34, Marcel Dekker Inc. Barcelona（in
11）Mishra, S.; Tyagi, V. K. Synthesis and characterization Spain）（1996）.

670
J. Oleo Sci. 65, (8) 663-670 (2016)