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Amine Oxides Review PDF
Amine Oxides Review PDF
Edited by M. Iwahashi, Kitasato Univ., and accepted September 20, 2005 (received for review August 29, 2005)
Abstract: Amine oxides are amine-based surfactants, represent one of the smaller classes
of surfactants as compared to alcohol ethoxylates and sulfonated and sulfated anionic
surfactants. However, the uniqueness of the hydrophile in such surfactants provides specific
properties that are difficult, if not impossible, to replicate by the use of classic nonionic and
anionic surfactants. The aim of the present paper is to survey the most important developments
and understandings of the chemistry of amine oxide production, it’s physico-chemical studies,
applications and environmental properties.
Key words: amine oxide, amine-based surfactant, hydrophile, physico-chemical,
environmental
*
Correspondence to: V.K. TYAGI, Department of Oil and Paint Technology, Harcourt Butler Technological Institute, Kanpur - 208002, INDIA
E-mail: vinod_tyagi1960@yahoo.com, sudhir_s6@rediffmail.com
γ ( R NO ) = k 3 [ R 3 N.H 2 O 2 ]∗ ・・・・・・・・・・・・・・・・・・・(I)
3
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Amine Oxides: A Review
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
S.K. Singh, M. Bajpai and V.K. Tyagi
attributed to the electrostatic shielding effect of counter- water soluble polymers poly (vinyl methyl ether)
ions on the charged micelle. Ikeda et al. (14) studied (PVME), poly (propylene oxide) (PPO), and poly (ethy-
the effects of ionization on micelle size of aqueous lene oxide) (PEO) on the aggregation behaviour of n-
NaCl solution of dimethyldodecyl amine oxide, by dodecyldimethyl amine oxide (DDAO), at various
using the light-scattering method for the determination stages of protonation.
of molecular weight, from the Debye plot. Hoffman et al. (20) reported the phase diagram of the
Imae and Ikeda (15) measured angular dependence of ternary surfactant system tetradecyldimethyl amine
light-scattering from micellar solutions of dimethyl- oxide / heptanol / water for small surfactant concentra-
oleyl amine oxide in water and 10-4 M NaCl at different tions. With increasing cosurfactant / surfactant ratio, the
micelle concentrations from the critical micelle concen- generally observed sequence of the phases L1, La and
tration (CMC) to 0.15 × 10-2 g cm-3. The intensity of L3 is found. These single phases are separated by nar-
light scattered from the micellar solutions increases row two phase regions. In all these phases the L3 or so-
with an increase in scattering angle, in contrast to the called sponge phase has drawn much attention. It is a
usual behaviour. This is caused by the effect of external low viscous, slightly turbid, and optically isotropic
interference which is stronger than that of internal inter-
ference.
Dimethyldodecyl amine oxide and dimethyltetrade-
cyl amine oxide are known to form spherical micelles
in water and 0.20 M NaCl solutions; but, if the hydro-
carbon part of nonionics with amine oxide head group
is made longer for e.g. dimethyloleyl amine oxide,
forms rod like micelles in dilute aqueous solutions
determined from light-scattering measurements. Ritsu
Kamiya et al. (16) presented electron micrographs of
rod like micelles regenerated from aqueous solutions of
dimethyloleyl amine oxide and gave support for the Fig. 2 The Phase Diagram under the Visual Inspection for
results from the light scattering measurements. Aqueous Solutions of C16 DAO. I, Transparent and
Imae and Ikeda (17) investigated the pH dependence Isotropic Solution; II, Turbid Solution; III,
of upper and lower consolute phase boundaries for Iridescent Solution.
aqueous NaCl solutions of dimethyloleyl amine oxide Reprinted from J. Colloid Interface Sci., Vol. 131, 601-602,
Copyright with permission from Elsevier.
at temperatures between 5 and 85℃ for pH less than 8
at different NaCl concentrations. The consolute phase
boundary is also given as a function of surfactant con-
centration. Toyoko Imae et al. in their another investi-
gation (18) found that aqueous solutions of dimethyl-
alkyl amine oxides (CnDAO, n = 16,18) present the iri-
descence at surface concentrations of 0.3 - 2 wt%, when
the temperature of the solutions is lower than 23℃ for
C16 DAO and 46℃ for C18 DAO. The Colour changes
from yellowish red to blue with an increase in surfac-
Fig. 3 The Phase Diagram under the Visual Inspection and
tant concentration, and disappears at pH below Ca.
the Crossed Nicol for Aqueous Solutions of
6.5 for C16 DAO and below Ca. 4.5 for C18 DAO (see C 18 DAO.――, visual inspection; ― - ― - ― - ―,
Figs. 2 & 3). crossed nicol. I, transparent and isotropic solution;
Polymer-micelle complexes have found applications II, turbid solution; III, iridescent solution; IV,
in many industrial products, such as paints and coat- weakly birefringent solution; V, strongly
ings, laundry detergent, and cosmetic products and they birefringent solution.
also play a role in tertiary oil recovery. Brackman and Reprinted from J. Colloid Interface Sci., Vol. 131, 601-602,
Engberts (19) studied the influence of the nonionic Copyright with permission from Elsevier.
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
Amine Oxides: A Review
phase which shows flow birefringence under shear. It is very interesting to investigate the behaviour of
The interactions between water and nonionic surfac- surfactant mixtures, which have different head groups
tants are important in both fundamental and applied with synergistic interactions but also different chains
surface chemistry. Mol et al. (21) determined the struc- with antagonistic interactions. Hoffman and Possnecker
tural parameters of the hexagonal and lamellar phase of (23) investigated the mixing behaviour of surfactants by
the dimethyldodecyl amine oxide (DDAO)- water sys- using the phase separation model. In their investigation
tems using X-ray diffraction. The result obtained are they used pairs of nonionic hydrocarbon surfactants and
discussed in the light of the on going debates about (i). perfluorinated anionic surfactants; in one example they
The relative importance of steric / protrusion forces and took the tetradecyldimethyl amine oxide as nonionic
hydration forces between surfactant bilayers and (ii) the surfactant with the mentioned anionic surfactants. With
molecular origin of the temperature dependence of the this anionic surfactant it was possible to reach nearly
interactions displayed in several nonionic water sys- identical CMC values of the nonionic and the anionic
tems. surfactant. To create special starting conditions, they
The electrostatic potential is one of the important used a hydrophobic tetraethyl ammonium counterion of
factors for the stabilization of dispersed colloidal parti- the anionic surfactant (see Figs. 8 & 9).
cles in aqueous medium. The electrokinetic phe- Desnoyers et al. (24) studied the thermodynamic
nomenon such as electrophoresis, which may be evalu- micellar properties of n-octyldimethyl amine oxide
ated by mobility, is in close connection with electrostat- hydrochloride (OAO.HCl) in water. The apparent molar
ic potential. Imae and Hayashi (22) performed elec- volumes and heat capacities of OAO. HCl were meas-
trophoretic light scattering measurements for aqueous
NaCl solutions of dodecyl-, tetradecyl-, and
oleyldimethyl amine oxides (C 12 DAO, C 14 DAO &
ODAO). It was observed that Electrophoretic mobility
changed with the degree of protonation (see Figs. 4 to
7).
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
S.K. Singh, M. Bajpai and V.K. Tyagi
104
J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
Amine Oxides: A Review
105
J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
S.K. Singh, M. Bajpai and V.K. Tyagi
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
Amine Oxides: A Review
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
S.K. Singh, M. Bajpai and V.K. Tyagi
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
Amine Oxides: A Review
7
Fig. 27 Li Double-Quantum Filtered Spectra of Lithium-
Fig. 25 (a) An IR RA Spectrum of a One-Layer LB Film
Exchanged Laponite Suspended in Water (Clay
of C 18 DAO on a Gold-Evaporated Glass Slide
Content, 17.8 g/L; Li+ Concentration, 13.0 mM)
Prepared from the Aqueous Subphase at pH 3.0.
(Top, q = 90°; Bottom, q = 54.7°).
(b) An IR Transmission Spectrum of a One-Layer Reprinted from J. Colloid Interface Sci., Vol. 236, 290-294,
LB Film of C18DAO on a CaF2 Plate Prepared from Copyright with permission from Elsevier.
the Aqueous Subphase at pH 3.0.
Reprinted from Langmuir, Vol. 15, 6890-6896, Copyright
with permission from Am. Chem. Soc.
7
Fig. 28 Li Double-Quantum Filtered Spectrum (q =
54.7°) of Lithium-Exchanged Saponite (Charge
0.35)(Clay Content, 40.0 g/L; Li+ Concentration,
37.1 mM) Suspended in Surfactant Solution (0.1
Fig. 26 (a) An IR RA Spectrum of a One-Layer LB Film M).
of 2C 18 DAC on a Gold-Evaporated Glass Slide Reprinted from J. Colloid Interface Sci., Vol. 236, 290-294,
Prepared from the Aqueous Subphase at pH3.0. (b) Copyright with permission from Elsevier.
An IR Transmission Spectrum of a One-Layer LB
Film of 2C18DAC on a CaF2 Plate Prepared from tion, the surface electric potentials were estimated.
the Aqueous Subphase at pH 3.0. Kawasaki and Maeda (38) used Fourier-transform
Reprinted from Langmuir, Vol. 15, 6890-6896, Copyright infrared spectroscopy (FT-IR) coupled with attenuated
with permission from Am. Chem. Soc. total reflection (ATR) to investigate the proposed H-
bond between the head groups of C12 DAO (a = 0.5) in
persed in surfactant solutions (see Figs. 27 & 28). both an aqueous medium and the solid state. To clarify
Kakehashi et al. (37) examined the effects of the this hydrogen bond (H-bond), they focused on the OH
hydrocarbon chain length, the bulkiness of the polar band of the headgroup of C12 DAO (a = 0.5 and 1) in
head group, the added salt concentration, the surfactant this study (see Figs. 29 to 32).
concentration, and temperature on the hydrogen ion Dielectric relaxation spectroscopy is a very powerful
titrations of amine oxides. The surfactants studied are method to investigate the motion of molecules possess-
alkyldimethyl amine oxides (CnDAO) with hydrocarbon ing electric dipole moments. Itatani and Shikata (39)
Chain lengths of 10-16, and N,N-bis(2-hydroxy ethyl) examined the dielectric relaxation behaviour of aque-
alkyl amine oxide (CnDHEAO) with hydrocarbon chain ous dodecyldimethyl amine oxide (DDAO) solutions by
lengths of 10-14. From the results of hydrogen ion titra- changing the concentrations of DDAO, NaBr and the
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
S.K. Singh, M. Bajpai and V.K. Tyagi
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
Amine Oxides: A Review
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
S.K. Singh, M. Bajpai and V.K. Tyagi
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Amine Oxides: A Review
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S.K. Singh, M. Bajpai and V.K. Tyagi
Fig. 42 Laundry Rinse: Whiteness Rating. Variability = ± Fig. 45 Laundry Rinse Synergy: Whiteness Rating.
0.5 for 95% confidence level. Variability = ± 0.5 for 95% confidence level.
Reprinted from J. Am. Oil Chem. Soc., Vol. 69, 682-689, Reprinted from J. Am. Oil Chem. Soc., Vol. 69, 682-689,
Copyright with permission from Am. Oil Chem. Soc. Copyright with permission from Am. Oil Chem. Soc.
Fig. 43 Laundry Rinse: Wetting Rating after Four Cycles. Fig. 46 Laundry Rinse Synergy: Wetting Rating after Four
Reprinted from J. Am. Oil Chem. Soc., Vol. 69, 682-689, Cycles.
Copyright with permission from Am. Oil Chem. Soc. Reprinted from J. Am. Oil Chem. Soc., Vol. 69, 682-689,
Copyright with permission from Am. Oil Chem. Soc.
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Amine Oxides: A Review
Fig. 49 Laundry Detergent: Whiteness Rating. Variability Fig. 52 Dryer Sheet Synergy. Softness rating. Variability =
= ± 0.5 for 95% confidence level. ± 0.3 for 95% confidence level.
Reprinted from J. Am. Oil Chem. Soc., Vol. 69, 682-689, Reprinted from J. Am. Oil Chem. Soc., Vol. 69, 682-689,
Copyright with permission from Am. Oil Chem. Soc. Copyright with permission from Am. Oil Chem. Soc.
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J. Oleo Sci., Vol. 55, No. 3, 99-119 (2006)
Amine Oxides: A Review
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