WATER NUMBER OF SELECTED SURFACTANTS

Dobrawa Kwaśniewska*, Daria Wieczorek, Ryszard Zieliński

Poznan University of Economics and Business, Faculty of Commodity Science,
Department of Technology and Instrumental Analysis
* corresponding author: Al. Niepodleglosci 10, 61-875 Poznan, Poland,
dobrawa.kwasniewska@ue.poznan.pl

Abstract: Surfactants are a large group of organic compounds, commonly used

as active ingredients of a number of products as well as some modifiers of product’s
or process quality. A characteristic feature of surfactants is their chemical structure.
In general, they contain two parts: hydrophilic head group and hydrophobic tail.
Hydrophobic part is usually built by hydrocarbon chain of unbranched or branched
structure. In turn, polar head groups provide solubility in water or other polar liquid.
Basically, surfactants heads are formed by a dissociable groups (acidic or basic)
or nonionic group. Based on dissociation ability of polar heads in water one can
distinguish anionic, cationic, zwitterionic and nonionic surfactants.
Unique structure of surfactants provides them many extraordinary properties such as:
micellisation, detergency, solubilisation, wetting, foaming or defoaming, emulsi-
fication or demulsification [Farn 2006]. This fact entails numerous areas of surfactants
applications of which the most important are: the production of textiles, cosmetics,
household chemistry products and pharmaceuticals [Zoller 2009]. Rapidly increasing
size of the global market and multitude of surfactants applications clearly indicates
that nowadays they undoubtedly become an integral part of our everyday life.
Some literature reports mention that the most significant property of surfactants is
their hydrophile-lipophile balance (HLB) introduced by Griffin [Proverbio et al.
2003]. The numerical value of HLB is regarded as a quantitative measure of the effect
of hydrophilic and lipophilic part of surfactant/s molecule on its behaviour in aqueous
solutions being a valuable source of information on potential application of a given
surfactant.
We have experimentally determined the values of “water number” (WN) for several
surfactants. The aim of this study was to correlate our experimental WN values

91
determined for various surfactants with the value of HLB for those surfactants
computed using both Davies and ECL methods. The second purpose of the study
was the assessment of the possibilities to use the method to determine the value
McGowan HLB sulfobetaines.

Keywords: surfactants, HLB, water number, Davies method, ECL method

1. INTRODUCTION

Surfactants are varied groups of chemicals compounds which

characterized by structure. In one molecule they have at once hydrophobic
and hydrophilic group. Most often hydrophobic groups are constructed by long
alkyl chain, sporadically by halogenated or oxygenated hydrocarbon chain
[Rosen and Kunjappu 2012]. Hydrophilic groups (heads) are generally polar
and they demonstrate affinity for water and other polar liquid. Heads could
contain in structure diverse functional groups. Due to the fact that
the hydrophobic part is usually alkyl chain the head is that part that determine
the properties, and therefore surface active agents are classified depending
on the character of hydrophilic groups [Rosen and Kunjappu 2012, Zieliński
2013]. Hence, it can be distinguished: anionic, cationic, zwitterionic
and nonionic surfactants.
In structure of anionic surface active agents hydrophilic groups are most
often built by carboxylates, sulphates, sulphonates or phosphates. Currently,
these types of surfactants found the most extensive application in industrial
[Tadros 2005].
Most popular cationic surfactants are quaternary ammonium salt
and their derivatives for example gemini compounds. But heads of cationic
surfactants can be also crate by cyclic moiety. Nowadays are synthesized
cationic surfactants which are derivatives of: imidazole, morpholine
or pyridine [Tadros 2005, Myers 2006].

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 In turn characteristic for zwitterionic surfactants is that they contain
in one head positive and negative charge. Literature the most common
described aliphatic zwitterionic surfactants which are derivatives
of: alkylbetaines, alkylamidebetaines [Garcia et al. 2008], sulfobetaines
[Qu et al. 2011], homogemini betaines [Xie and Feng 2011] and heterogemini
betaines [Kwaśniewska et al. 2015].
In molecules of nonionic surfactants hydrophilic group is devoid
of charge. Nonionic surface active agents which are the most commonly used
in industrial are: alcohol ethoxylates, fatty acid ethoxylates and amine
ethoxylates [Tadros 2005].
Unique structure of surfactants provide them many extraordinary
properties the most important are: wetting, foaming or defoaming,
emulsification or demulsification, micellisation, detergency [Farn 2006].
This fact entails numerous areas of surfactants applications. Surfactants are
used in production of: cosmetics and personal care products, pharmaceuticals,
textiles and fibres, leather and furs. Moreover, the production of paints,
lacquers paper, cellulose products and plastics and composite materials require
the use of surfactants [Myers 2006]. Surface active agents have also
nontraditional applications. Nowadays they play an important role
in the preparation of biomedical [Yuan 2008] and antiadhesive materials
[Cheng et al. 2007]. Cationic and zwitterionic surfactants exhibit biocidal
properties and therefore they are used as active ingredients in disinfectants
products [Obłąk and Gamian 2010]. Surfactants are also used in medicine
especially in neonatology and in treatment of RDS [Wilson et al. 2005].
In medicines some surfactants are present as active ingredients or as auxiliary
ingredients in the production of tablets and suspensions. The addition
of surface-active substances may be also useful and frequently it significantly
increases a pharmaceutical and biological availability and activity of drug as

93
well as they could affect the drugs resorption. Moreover, some groups
of surfactants are also used in the preparation of permanent suspensions
[Danek 1977, Dąbrowa et al. 2008].
Some literatures mention that the most significant property of surfactants
is their hydrophile-lipophile balance (HLB) [Proverbio et al. 2003].
The practical application of surfactants determines the ratio between
the hydrophilic and hydrophobic part of compound (HLB). This system
enables to set in order information about surfactants and helps in the selection
of appropriate systems for the composition of various formulations, including
emulsion [Sikora 2014].
HLB concept was developed by Griffin more than six decades ago
[Al-Sabagh 2002]. There are several methods of determining HLB value,
among them experimental or computational. Experimental methods are usually
specific and concern not large groups of surfactants sometimes even
homologous series. The most popular computational methods are Griffin’s,
Davies and McGowan’s methods [Zieliński 2013].
Griffin’s method allowed the observation of relationship between
hydrophile-lipophile structures of surfactant’s molecule with properties
[Zieliński 2013]. Initially Griffin conducted researches which were based
on determination of emulsion stability [Proverbio et al. 2003]. On this basis
he proposed method which was based on the calculation value of hydrophile-
lipophile balance according to the formula where Mp is molecular weight
of the polar part of nonionic surfactant molecule and M is molecular weight
of the whole molecule [Griffin 1949, Griffin 1954, Zieliński 2013]:
"#
!" = 20 ! $$$$$$(1)
"

94
 Griffin’s observation led to the designation of numerical scale of HLB,
according with this HLB value for: solubilising, detergents, O/W emulsifiers,
wetting agents, W/O emulsifiers and defoamers is in the ranges respectively:
15-18, 13-15, 8-18, 7-9, 4-6 and 1-3 [Griffin 1949]. Griffin’s method is not
complicate but it is worth remembering that this method gives only
approximate results [Zieliński 2013].
As a result subsequently research on the topic hydrophile-lipophile
balance Davies suggested a new method for calculating the value HLB.
This method is based on the chemical groups of the molecule contributions
described by the following formula [Davies 1957]:

%&'* = 7 + , -./345-6869$:34;5$<;>?@3A

+ , 86545-6869$:34;5$<4;>?@3A$$$$(2)

where the group numbers were assigned to various structural elements

[Guo et al. 2006]. Generally hydrophilic group numbers have positive value
and hydrophobic group numbers have negative one [Zieliński 2013]. Literature
reports also on modification of Davies method. For surfactants which contain
in molecule straight alkyl chain, polyoxyethylene chain or polyoxypropylene
chain, Davies equilibrium should be written:

%&'* = 7 + B%CDE × FCDE GHII + BFJK × FJKGHII + BFLK × FLKGHII

+ ,(4M-@3$-./345-6869$:34;5A)

+ ,(4M-@3$86545-6869$:34;5A)$$$(N)

95
where NCH2,eff , NEO,eff , and NPO,eff represent the effective chain length for
–CH2–, EO, and PO groups [Guo et al. 2006].
Effective chain length of -CH2-, EO and PO groups can be calculated
according to the following equations:

FCDEGOPP = 0QRST × FCDE U 0Q17V$$$$$$FCDE W T0$$$$$$$(X)

FJKGHII = 1NQXT ln(FJK ) U 0Q1SFJK + 1Q2S$$$$$1 Y FJK Y T0$$$$$$$(T)
FJKGHII = 0Q0TSFJK + XNQ0V$$$$$FJK Z T0$$$$$$$(S)
FLKGHII = 2Q0T7FLK + RQ0S$$$$$$(7)

In addition, a modification of the Davies method proposed Rideal.

This modification was based on the introduction of equilibrium HLB value
(HLBs), calculated with the formula:
9]
%&'[ = 7 U 0QV2R ! log \ _$$$$$$(V)
9^
were the value of cw is known as the solubility of the surfactant in water
and co is solubility of the surfactant in oil. This method, like other presented
methods is not perfect and very often obtained results do not correspond to real
value [Ogonowski and Tomaszkiewicz-Potępa 2004].
Another method of calculation of HLB was suggested by McGowan.
According to this method, HLB value is calculated by a simple summation
of the shares of groups of atoms and bonds according to the following formula:

%&'` = 7 + ,(A-a3@$:34;5A)$$$$$$$(R)

In the absence of relevant date to calculate the hydrophile-lipophile

balance can be estimated using the formula [Apostoluk and Szymanowski
1998, Zieliński 2013,]:

96
 %&'` = 7 + 1QT<b U 0Q0N77cd $$$$$$$(10)

where nh is hydration number of parts of the polar molecule and Vx

is the characteristic McGowan molar volume of molecule [Zimoch et al. 2000].
This parameter can be calculated according to the model:

cd = , <e ! cdf U SQTS ! '$$$$$$(11)

where B is the number of bonds (defined by the formula: B=N+R-1),

N is the total number of atoms of the surfactant molecule (except for counter-
ions), R is the number of rings in a surfactant molecule and Vxi
is the characteristic molar volume of atoms [Zieliński 2013].
Presented methods can only be used to estimate the HLB value
of surfactants therefore it was developed a number of methods of determining
HLB value based on measurement of physicochemical properties. It should
be remembered that the methods based on the measurement
of physicochemical properties often are applied only to determine HLB value
of small groups of surfactants.
For polyethoxylated fatty acids the HLB value is defined based
on experimental determination of the saponification number (S) and acid
number (A) of corresponding surfactants. The working relationship is
described by the following formula [Ogonowski and Tomaszkiewicz-Potępa
2004]:
h
%&' = 20 ! \1 U _$$$$$$(12)
i

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 In a thin-layer chromatography the retention coefficient can also be used
to determine the HLB value. According to literature [Ogonowski and
Tomaszkiewicz-Potępa 2004] for poliethoxylated alcohols and poliethoxylated
alkylphenols the HLB value is determined based on the retention coefficient
of two eluents such as ethanol (REtOH) and hexane (RHex) and this dependence
is represented by the following empirical formula:

%&' = VQTT ! j U SQNS$$$$$$$(1N)

kJmKD
j= $$$$$$(1X)
kDHd

A very simple and rapid method for estimation the HLB value for various
surfactants was proposed by Becher. This test is based on empirical
determination of the capacity for spilling toluene on surface of aqueous
solution of surfactant. The obtained results are compared with the spilling
diagram for references aqueous solution of surfactant [Ogonowski
and Tomaszkiewicz-Potępa 2004].
The HLB value may be also determined based on the 1H NMR spectra
determined for aqueous solutions. For nonionic surfactants being derivatives
of ethylene oxide the relationship between the HLB value and the 1H NMR
data is described by the formula:
i!%
%&'Dp`q = $$$$$$$(1T)
0Q0T ! (i ! % + ' ! &)

where A and B are constants for nonionic surfactants equal to 15 and 10

respectively, H is a height (mm) of the curve of integration for protons from
hydrophilic groups, and L is a height (mm) of the curve of integration
for protons from hydrophobic groups in the 1H NMR spectra [Ogonowski
and Tomaszkiewicz-Potępa 2004].

98
 In determining the value of hydrophile-lipophile balance may be also
helpful a knowledge of water number. The water number is determined
by surfactant solution (in a mixture of 1,4-dioxane and benzene) titration using
the water, to the appearance of the first turbidity [Verdinelli et al. 2008].
The relationship linking the “water number” (WN) with HLB value
can be expressed by the following equation [Ogonowski and Tomaszkiewicz-
Potępa 2004]:

%&' = > ! 84:rF U <$$$$$$$(1S)

were m and n are constant determined experimentally.

Otherwise, the correlation between the WN vale and the HLB value
described by Karabinos for few surfactants is as follows [Ogonowski
and Tomaszkiewicz-Potępa 2004]:

%&' = 0QVR ! rF + 1Q11$$$$$$$(17)

In this study we present the results of our determination of the water

number for several ionic surfactants. The aim of the study was to find
the correlation between experimentally determined WN values for surfactants
with the HLB values calculated using both Davies and ECL methods.

2. MATERIALS AND METHODS

In experiment the following compounds was applied: hexamethy l-1,6-

bis- (N- dodecyl- N- methylammonio- N- propylsulfonate) (DMH- 12(C3S)2)
and N- dodecyl- N- methyl- N- (3- sulfopropyl)- 6- (N- do- decyl- N
methylamino) hexylammonium chloride (DMH-12C3S*HCl) [Kwaśniewska
and Zieliński 2013, Kwaśniewska 2014; Kwaśniewska et al. 2015].
The structure of these compounds are shown in figures 1 and 2. Moreover,

99
in the experiment were used popular surfactants such as: sodium dodecyl
sulfate, cetyltrimethylammonium bromide and Brij 30. Solvents that were used
in the study were prepared by mixing 1,4-dioxane and benzene in the ratio:
96:4 (v/v).
SO3

O3S N N

C12H25 C12H25

Figure 1. Structure of hexamethyl-1,6-bis-(N-dodecyl-N-methylammonio-N-propyl

sulfonate). Source: Authors’ own work

Figure 2. Structure of N-dodecyl-N-methyl-N-(3-sulfopropyl)-6-(N-dodecyl-N-

methylamino)hexyl ammonium chloride. Source: Authors’ own work

The aim of study was to find a correlation between experimentally

determined values of the “water number” (WN) with computed values of HLB
for various surfactants. The purpose of the study was also the assessment
of the possibilities to use the McGowan method to determine the value HLB
of sulfobetaines.
To determine the numerical value of “water number” the following steps
have been taken. First, for each surfactant we have prepared a solution
by dissolving 0,1g of a suitable surfactant in 3 cm3 of 1,4-dioxane and benzene
(96:4, v/v) mixture. Subsequently, the resulting solution was titrated
with double distilled water until persistent turbidity was obtained. The amount
of water added to the surfactant solution at turbidity is known as the “water
number”.
100
3. RESULTS AND DISCUSSION

For estimating the value of HLB of surfactants some computational

methods were applied. Generally, HLB values for surfactants obtained
by a calculation based on McGowan, Davies or Griffin methods differ for each
other. Initially for hexamethyl-1,6-bis-(N-dodecyl-N-methylammonio-N-
propylsulfonate) and N-dodecyl-N-methyl-N-(3sulfo propyl)-6-(N-dodecyl-
N-methylamino)hexylammonium chloride was made an attempt to determine
the HLB value by McGowan method (Table 1) but obtained results
were significantly overestimated.

Table 1. HLB value calculated according to the method of McGowan

Compound HLBM

DMH-12(C3S)2 30.63
DMH-12C3S*HCl 19.14
Source: Authors’ own work

Presented in table 1 results indicate that application of the McGowan’s

method is not suitable for estimating the HLB value of the compounds having
a sulfobetaine structure. This fact can be explained due to the fact
that these surfactants contain in the molecule two sulfonate groups and in the
case of DHH-12(C3S)2 also two groups of quaternary nitrogen atoms.
However, due to the close location the cationic and anionic centers in molecule
of sulfobetaines, sulfonate group probably does not have a fully anionic
character. In turn McGowan method does not account for such a situation.
In addition, the calculated HLB values seem too high because it does not
correspond to the actual properties of the tested sulfobetaines.

101
 Due to the fact that the McGowan method turned out to be inadequate
the water number for homogemini sulfobetaine and chloride of heterogemini
sulfobetaine with two 12-carbon length chain was determined. Based on
the obtained experimental data, it was made attempt to determine HLB values.
The literature contains a number of experimental data correlating value
of water number with HLB values calculated based on Davies method
[Verdinelli et al. 2008], but generally these data are described only for
compounds having a relatively low HLB values. For this reason, it was decided
to correlate our experimental values of the water number of surfactants having
higher HLB values. Therefore, we have determined the values of “water
number” for the following surfactants: CTAB, SDS and Brij30.
The experimental values of water number obtained for those surfactants
are presented in Table 2.

Table 2. Values of water number and HLBECL for several surfactants

Compound Water number [cm3] HLBECL

SDS 42 40.0

CTAB 33 21.8
Brij30 19 10.2
DMH-12(C3S)2 20 10.4
DMH-12C3S*HCl 21 11.4
Source: Authors’ own work

Moreover, it was decided to correlate the number of experimentally

available values of water number for surfactants with the HLB values
calculated using the ECL method which is a modification of the method
proposed by Davies. In the case of shares of cationic groups benefited from

102
the numerical values of the shares of these groups published by the company
AKZO Nobel [Reference Library 2011]. Calculated HLBECL values
and our experimentally determined values of the “water number” for several
popular surfactants and selected literature data available [Verdinelli
et al. 2008] allowed us for the evaluation of the calibration curve with equation:

!"#$% = 0.9372 & !' ( 8.3034)))))))*18+)))

ND = 7, r2 = 0.9703, f = 5, F = 229.05, DSeRess = 2.42

where: ND – number of data points,

r2 - squared correlation coefficient,
f – degree of freedom,
F – Snedecor F function,
DSeRess – residual standard deviation

45
40
35
30
25
HLBD

20
15
10
5
0
0 10 20 30 40 50
Water number [cm3]

Figure 3. Dependency graph of water number and HLB value for several standard
surfactants. Source: Authors’ own work

103
 Our calibration curve, (shown in Fig. 3) was prepared on the basis
of the values of the “water number” and the HLBECL value allowed
us to estimate the value of HLB for two novel surfactants: homogemini
sulfobetaine and heterogemini sulfobetaine chloride. HLBECL values
for hexamethyl-1,6-bis-(N-dodecyl-N-methylammonio-N-propylsulfonate)
and N-dodecyl-N-methyl-N-(3-sulfopropyl)-6-(N-dodecyl-N-methylamino)
hexylammonium chloride are equal to 10.4 and 11.4 respectively.

4. CONCLUSIONS

Based on calculations it can be concluded that commonly used methods

for estimating the HLB values do not allow for accurate determination
of this parameter for sulfobetaines. According to our laboratory assay
of the water number it can be seen that determination of the HLB value
is rather simply and more accurate than other methods. Therefore, it seems
that the proposed method based on experimental determination of the “water
number” could be helpful in evaluation of the HLB values for surfactants
having a sulfobetaine structure.

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STRESZCZENIE

Surfaktanty są obszerną grupą związków organicznych powszechnie stosowanych,

jako składniki aktywne wielu produktów. Charakterystyczną cechą środków
powierzchniowo czynnych jest ich struktura chemiczna. Zwykle zbudowane
są z dwóch części: hydrofilowej głowy i hydrofobowego ogona. Część hydrofobowa
najczęściej jest budowana przez nierozgałęziony bądź rozgałęziony łańcuch
węglowodorowy. Z kolei polarne głowy zapewniające rozpuszczalność we wodzie
lub innej cieczy polarnej tworzone są zwykle przez reszty kwasowe lub zasadowe.
W oparciu o charakter głów można wyróżnić surfaktanty: anionowe, kationowe,
zwitterjonowe oraz niejonowe.
Wyjątkowa struktura surfaktantów zapewnia im wiele niezwykłych właściwości
takich jak: zdolność do tworzenia micel oraz piany a także właściwości piorące,
zwilżające, emulgujące [Farn 2006]. Wszystko to sprawia, iż surfaktanty znalazły
liczne obszary zastosowania, z pośród których najważniejsze to: przemysł tekstylny,
kosmetyczny, chemii gospodarczej i farmaceutyczny [Zoller 2009]. Gwałtowny

107
wzrost rynku surfaktantów oraz obszarów ich zastosowań świadczy o tym, iż związki
powierzchniowo czynne są integralną częścią naszego życia codziennego.
Niektóre doniesienia literaturowe wspominają że niezwykle istotne ze względu
na praktyczne wykorzystanie surfaktantów jest poznanie wartości wskaźnika
równowagi hydrofilowo-lipofilowej (HLB) wprowadzonego przez Griffina
[Proverbio i in. 2003]. Wskaźnik HLB jest ilościową miarą, określającą w umowny
sposób udział fragmentu hydrofilowego i lipofilowego w cząsteczce surfaktantu.
Celem pracy było skorelowanie wartości liczby wodnej kilku surfaktantów
z wartością HLB obliczoną za pomocą metody Davies i ECL.

Słowa kluczowe: surfaktanty, HLB, liczna wodna, metoda Daviesa, metoda ECL

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