Journal of Oleo Science

Copyright 2008 by Japan Oil Chemists Society

J. Oleo Sci. 57, (10) 529-538 (2008)

Aquatic Toxicity and Biodegradability of

Advanced Cationic Surfactant APA-22
Compatible with the Aquatic Environment
Masayuki Yamane1, Takamasa Toyo1, Katsuhisa Inoue2, Takaya Sakai2,
Youhei Kaneko2 and Naohiro Nishiyama1
1
2

Safety Science Research Laboratories, Kao Corporation (2606 Akabane, Ichikai machi, Haga-gun, Tochigi 321-3497, JAPAN)
Material Science Research Laboratories, Kao Corporation (1334, Minato, Wakayama-shi, Wakayama 640-8580, JAPAN)

Abstract: Cationic surfactant is a chemical substance used in hair conditioner, fabric softener and other
household products. By investigating the relationship between the aquatic toxicity and the chemical
structures of two types of mono alkyl cationic surfactants, alkyl trimethylammonium salts and alkyl
dimethylamine salts, we have found that the C22 alkyl chain length is effective to reduce the toxicity.
Besides, we have recognized that the amidopropyl functional group contributes to the enhanced
biodegradability by investigating the biodegradation trend of (alkylamidopropyl)dimethylamine salt (alkyl
chain length: C18). Based on these findings, we have developed mono alkyl cationic surfactant called APA22, N-[3-(dimethylamino)propyl]docosanamide salt. APA-22 is formed by the C22 alkyl chain,
amidopropyl functional group and di-methyltertiary amine group. We evaluated the aerobic and anaerobic
biodegradability of APA-22 by two standard methods (OECD Test Guideline 301B and ECETOC technical
document No.28) and found that this substance was degraded rapidly in both conditions. The toxicity to
algae, invertebrate and fish of this substance are evaluated by using OECD Test Guideline 201, 202 and
203, respectively. All acute toxicity values are >1 mg/L, which indicates that environmental toxicity of this
substance is relatively less toxic to aquatic organism. In addition, we estimated the biodegradation
pathway of APA-22 and observed the complete disappearance of APA-22 and its intermediates during the
test periods. Based on the environmental data provided above, we concluded that APA22 is more
compatible with the aquatic environment compared to other cationic surfactants with mono long alkyl
chain.
Key words: mono alkyl cationic surfactant, biodegradation, aquatic toxicity, environmental compatibility

1 INTRODUCTION
Cationic surfactant is an important chemical substance
and used for wide variety of hair conditioner, fabric softener and other household products. Therefore, cationic surfactant should be biodegradable and less toxic to aquatic
organisms. In addition, it is becoming more important to
develop a chemical substance with environmental compatibility, since chemical management such as REACH (Registration, Evaluation, Authorization of Chemicals), Detergent
Regulation in EU and GHS (Globally Harmonized System)
are getting more attention these days. Some cationic surfactants mainly used in fabric softener, such as esterquat,

DEEDMAC and esteramide, are known as biodegradable

and less toxic to aquatic organisms1-4). However, some of
the mono alkyl cationic surfactant is not-readily biodegradable and toxic to aquatic organisms. Masuda et al. reported
that alkyl trimethylammonium chloride (TAC) with C18
alkyl chain tends to be not-readily biodegradable because
of its inhibition for microorganisms5). Aquatic organisms
appear to be sensitive to cationic surfactant, and the toxicity of alkyl trimethyammonium bromide and alkyl
trimethylammonium chloride to algae is characterized by
EC50 below 1 mg/L6). LC50/EC50 of some TAC to invertebrate and fish is also reported below 1 mg/L7,8). Besides,

Correspondence to: Masayuki Yamane, Safety Research Laboratories, Kao Corporation, 2606 Akabane, Ichikai machi, Haga-gun, Tochigi
321-3497, JAPAN
E-mail: Yamane.masayuki@kao.co.jp
Accepted June 20, 2008 (received for review May 13, 2008)

Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 online

http://www.jstage.jst.go.jp/browse/jos/

529

M. Yamane, T. Toyo, K. Inoue et al.

OECD SIDS report summarized that one of the alkyl

dimethylamine salt (DMA), named N,N-dimethyldodecylamine, is also toxic to the aquatic organisms, whose toxicity to algae, daphnia and fish is below 1 mg/L9). Most of the
previous studies concluded that mono alkyl cationic surfactant tends to have adverse effect to the aquatic organisms and not-readily biodegradability when its alkyl chain
length increases. It is important to develop mono alkyl
cationic surfactants with no adverse effect to aquatic
organisms. Nevertheless, the study about developing the
eco-friendly mono alkyl cationic surfactant has not shown
much progress during the last decade. In order to develop
the modified mono alkyl cationic surfactant compatible
with the environment, we investigated the relationship
between the chemical structures of the cationic surfactants and their environmental properties (biodegradation
and aquatic toxicity). At first, we conducted the study to
find the relationship between alkyl chain length and the
environmental properties by comparing biodegradability
and toxicity of TAC and DMA. Second, we tried to find the
effect of intermediate functional group on the biodegradability and toxicity of the surfactants. On the basis of the
above evaluations, we developed mono alkyl cationic surfactant, named APA-22, N-[3-(dimethylamino)propyl]
docosanamide salt (AMIDET APA-22, Kao Chemicals
Europe, S.L.) whose surfactant property is excellent10) .
This substance consists of C22 alkyl chain, amidopropyl
functional group and di-methyl tertiary amine group. We
investigated the environmental compatibility of APA-22 by
evaluating its biodegradation, aquatic toxicity and
biodegradation pathway.

2 EXPERIMENTAL
2.1 Materials
Mono alkyl cationic surfactants used in this study are
alkyl trimethylammonium chlorides (TAC, alkyl chain
length: C12, C14, C16, C18, C22, C24), alkyl dimethylamine
lactic acids (DMA, alkyl chain length: C12, C14, C16, C18,
C20, C22) and (alkylamidopropyl)dimethylamine lactic acid
(APA, alkyl chain length: C18 and C22). Only APA-22 has
the distribution of alkyl chain length from C18 to C24. The
other surfactants reported in this study have no chain
length distribution. The chemical names, structures,
abbreviations and purity are shown in Table 1. These surfactants are synthesized by the Material Science Research
Laboratories, Kao Corporation, Wakayama, Japan.

followings. Usually, OECD TG 301C guideline recommends

that the concentrations of substance and standard activated sludge are 100 mg/L and 30 mg/L, respectively. In this
particular study, the concentration of substance and activated sludge collected from wastewater treatment plant
are 15 mg/L and 50 mg/L, respectively, to avoid the
inhibitory effect of these substances to microorganisms.
The biodegradability is calculated from Biochemical Oxygen Demand (BOD). Biodegradation of DMA-12, DMA-14,
DMA-16, DMA-18, DMA-20 and APA-22 are evaluated by
OECD TG 301B11), where the concentrations of substance
and activated sludge are 10 mgC/L and 30 mg/L, respectively, and biodegradability is calculated from evolved CO2.
The concentration of test materials and activated sludge of
OECD TG 301B and 301C used in this study is similar to
each other. Therefore, we can regard that biodegradation
of these surfactants is evaluated in a similar condition. In
addition, anaerobic biodegradation of APA-22 is evaluated
by the ECETOC technical document No. 28. BOD and Dissolved Organic Carbon (DOC) are analyzed by following
devices. BOD is measured by the coulometric oxygen
uptake recorder, OM3001 (Ohkura Electric Co. Ltd). DOC
is measured by the Total Organic Carbon analyzer, TOC5000A (SHIMADZU CORPORATION). The biodegradability value in Table 3 shows the average value (n=2).
Aquatic toxicity to algae, daphnia and fish of TACs (C12,
C14, C16, C18, C22), DMAs (C12, C14, C16, C18, C22) and
APAs is evaluated by OECD TG 20112), 20213) and 20314),
respectively. The eco-toxicity was calculated based on the
nominal concentration except for APA-22.
2.3 Estimation of biodegradation pathway of APA-22
In order to estimate the biodegradation pathway of APA22, biodegradation test using the river water is also evaluated. The river water was collected from Tagawa-river in
urban area of Utsunomiya, Tochigi prefecture, Japan. The
intermediates originated from APA-22 in the river water
were analyzed by proton Nuclear Magnetic Resonance (1HNMR) to identify their chemical structures, and DOC was
also analyzed at several sampling points to monitor the
reduction of organic matter. Test concentration of APA-22
set up to 30 mg/L in order to cover the limit of quantity
(LOQ) of DOC, though this concentration is relatively high
compared to the major surfactants monitored in urban
rivers in Japan15). River water of 400 ml sampled at 5-day
and 19-day is freeze dried up and dissolved in CD3OD solution of 3 mL. 1H-NMR of river water is measured by using
of Mercury-400 (Varian Corporation) in the method of nondecouple mode at the room temperature.

2.2 Evaluation of biodegradation and aquatic toxicity

The test condition details of biodegradation and aquatic
toxicity are shown in Table 2. The biodegradation of TAC18, TAC-20, TAC-22, TAC-24, DMA-22 and APA-18 is evaluated based on OECD Test Guideline (OECD TG) 301C11) as

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J. Oleo Sci. 57, (10) 529-538 (2008)

J. Oleo Sci. 57, (10) 529-538 (2008)

DMA-12
DMA-14
DMA-16
DMA-18
DMA-22
APA-18
APA-22

N,N-Dimethyldocecylamine lactic acid salt

N,N-Dimethyltetradecylamine lactic acid salt
N,N-Dimethylhexadecylamine lactic acid salt
N,N-Dimethyloctadecylamine lactic acid salt
N,N-Dimethyldocosylamine lactic acid salt

N-[3-(dimethylamino)propyl]octadecanamide lactic acid salt

N-[3-(dimethylamino)propyl]docosanamide lactic acid salt

98.3
99.2

97.8
98.4
98.5
98.9
98.5

98.7
99.7
99.7
99.6
95.7
98.0
97.0

Purity (%)

The weight percentage of alkyl chain length of APA-22 is followings; C18/C20/C22/C24 = 2.6%/6.8%/87.0%/1.7%.
The other materials have no distribution of alkyl chain.

TAC-12
TAC-14
TAC-16
TAC-18
TAC-20
TAC-22
TAC-24

Abbreviation

Chemical Names, Abbreviations, Purity and Structures of TAC, DMA and APA.

Dodecyl-N,N,N-trimethylammonium chloride
Tetradecyl-N,N,N-trimethylammonium chloride
Hexadecyl-N,N,N-trimethylammonium chloride
Octadecyl-N,N,N-trimethylammonium chloride
Icosyl-N,N,N-trimethylammonium chloride
Docosyl-N,N,N-trimethylammonium chloride
Tetracosyl-N,N,N-trimethylammonium chloride

Chemical name

Table 1
Structure

Aquatic Toxicity and Biodegradability of Advanced Cationic Surfactant APA-22

531

M. Yamane, T. Toyo, K. Inoue et al.

Table 2 Test Condition of Biodegradation and Aquatic Toxicity.

To avoid the inhibitory effect of substances to microorganisms, concentrations
of test material and activated sludge of OECD301C (modified) are 15 mg/L
and 50 mg/L, respectively.
Biodegradation
OECD301C (modifed)
Source of inoculum
Material concentration
Activated sludge concentration
Volume of nutrient medium
Test periods
Measured parameter

Activated sludge
(Moka sewage treatment plant)
15 mg/L
50 mg/L
300 mL
28 days
BOD, DOC

OECD301B
Source of inoculum
Material concentration
Activated sludge concentration
Volume of nutrient medium
Test periods
Measured parameter

Activated sludge
10 mgC/L
30 mg/L
3000 mL
28 days
Evolved CO2

Algae inhibition test (OECD201)

Species:
Incubation time:
Irradiation:
Temperature:
End point:

Desmodesmus subspicatus (CCAP276/20)

Pseudokirchneriella subcapitata (CCAP278/4)
72 hours
65 uEm2/s, continuously
22
Growth rate (ErC50)

Daphnia sp., acute immobilisation test (OECD202)

Species:
Incubation time:
Irradiation:
Temperature:
End point:

Daphnia magna
48 hours
Light/Dark=16/8 hours
20
Immobilisation (EC50)

Fish acute toxicity test (OECD203)

Species:
Incubation time:
Irradiation:
Temperature:
End point:

Oryzias latipes (Himedaka)

96 hours
Light/Dark=16/8 hours
25
Mortality (LC50)

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J. Oleo Sci. 57, (10) 529-538 (2008)

Aquatic Toxicity and Biodegradability of Advanced Cationic Surfactant APA-22

3 RESULTS
3.1 Biodegradability of tested materials
Table 3 shows the biodegradability of TACs (C18, C20,
C22 and C24), DMAs (C12, C14, C16, C18 and C22) and
APAs (C18 and C22). BOD of TACs ranges from 0 % (C22
and C24) to 40 % (C18). Degradability of DMAs calculated
from evolved CO2 and BOD ranges from 32 % to 100 %
(Table 3). The degradability of TAC and DMA with short
alkyl chain tends to be better than that of long alkyl chain.
The degradation of APA-18 and APA-22 are 93 % and 100
%, respectively. DMA-12, DMA-16 and APA-22 also passed
the criteria of 10 day-windows as readily biodegradable.
Anaerobic biodegradability of APA-22 evaluated by standard procedure is also 100%.
3.2 Aquatic toxicity of tested materials
The acute toxicity of TACs (C12, 14, 16, 18, 22) and
DMAs (C12, 14, 16, 18, 22) is shown in Fig.1. The acute toxicity (ErC50) of TACs and DMAs to algae ranges from
0.0092 to 0.52 mg/L, and most toxic alkyl chain of TAC and
DMA are observed at C14 and C16, respectively. The acute
toxicity (LC50) of TACs and DMAs to fish ranges from 0.11
to 22 mg/L, and most toxic chain length of TAC and DMA
are observed at C18 and C16, respectively. The acute toxicities (EC50) of TAC-22 and DMA-22 to daphnia are 0.044
and 0.97 mg/L, respectively. Figure 2 summarizes the
acute toxicity of APAs. The acute toxicity of APA-18 to
algae, daphnia and fish ranges from 0.08 to 0.30 mg/L. All
acute toxicity of APA-22 is over 1 mg/L, ranging from 1.4
to 6.6 mg/L.

Fig. 1 Toxicity Profile of TACs and DMAs to Algae (top)

and Fish (bottom).
Toxicities are calculated based on the nominal
concentration. The toxicity of TAC-22 and DMA-22
to daphnia is 0.044 mg/L and 0.97 mg/L,
respectively (It is not shown in Fig. 1).

Table 3 Biodegradability of TACs, DMAs and APAs.

Degradability evaluated by OECD301C is calculated from BOD. That of OECD301B is
based on the evolved CO2. Degradability shows the average value (n=2).
Test sample

Alkyl chain

Protocol

Degradability (%)

TAC

18
20
22
24

OECD301C (modified)
OECD301C (modified)
OECD301C (modified)
OECD301C (modified)

40
14
0
0

DMA

12
14
16
18
22

OECD301B
OECD301B
OECD301B
OECD301B
OECD301C (modified)

72
59
100
49
32

APA

18
22

OECD301C (modified)
OECD301B

93
100

DMA-12, DMA-16 and APA-22 also satisfied the 10 day-window criteria as readily biodegradable.

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J. Oleo Sci. 57, (10) 529-538 (2008)

M. Yamane, T. Toyo, K. Inoue et al.

lent. This indicates that the amidopropyl functional group

contributes to the enhanced biodegradability.

Fig. 2 Toxicity of APA-18 and APA-22 to Algae, Daphnia

and Fish.
Toxicities of APA-22 are calculated from the
measured concentration.

4 DISCUSSION
4.1 Biodegradation trend of tested mono alkyl cationic surfactants
The biodegradation of TACs is below 50% despite of
evaluating at low test concentration (15 mg/L). Especially,
BOD of TAC-22 and TAC-24 is 0 %, which shows that TAC
with long alkyl chain is not easily biodegradable. This
trend is similar to the previous study. Masuda et al. reported that the biodegradability of octyl and decyl trimethyl
ammonium chloride (TAC-08 and TAC-10) is over 60%,
while TAC with long alkyl chain length decreases degradability5). No degradation of TAC-22 and TAC-24 suggests
the occurrence of inhibition to microorganisms. On the
other hand, the degradability of DMA-12 and DMA-16 is
over 70% and passed the 10 day-window criteria, indicating that DMAs with shor t alkyl chain are readily
biodegradable. Besides, OECD SIDS report summarized
N,N-dimethyldodecylamine is readily biodegradable 9) ,
which is consistant with our data showing short alkyl
chain is more degradable. DMA-18 and DMA-22 show
degradability below 50%. As discussed in biodegradation of
TACs, DMA with long alkyl chain may also inhibit the oxygen consumption by microorganisms. However, DMAs
with long alkyl chain have a potential of biodegradation as
indicated by their degradability ranging from 32 % to 49 %.
Based on the relationship between alkyl chain length and
biodegradability of TACs and DMAs, we can conclude that
(i) DMA is relatively more biodegradable than TAC, and (ii)
short alkyl chains are more favorable for biodegradation
than long alkyl chains. On the other hand, differently from
the trends of TACs and DMAs, the biodegradability of
APA-18 is over 90 %, and that of APA-22 is also 100 % and
passed the 10 day-window criteria. Furthermore, anaerobic biodegradability of APA-22 is also 100 %, which indicates that APA-22 is completely degraded into the minerals
by microorganisms in the anaerobic conditions. They have
a long alkyl chain. Nevertheless, biodegradability is excel-

4.2 The relationship between aquatic toxicity and the

structure
The toxicity profile of TACs and DMAs to algae, daphnia
and fish is shown in Fig. 1 as a function of alkyl chain
length of the surfactants. The acute toxicity of TAC and
DMA to algae shows a parabolic trend. The most severe
toxicity of TAC and DMA to algae is observed at C14 and
C16 alkyl chain, respectively. The acute toxicity (LC50) of
TACs and DMAs to fish also shows a parabolic trend. The
lowest toxic value of TAC and DMA is observed at C18 and
C16 alkyl chain, which indicates that toxic effect is severe
around C16 and C18 alkyl chain. These parabolic trends
suggest that the toxicity of mono cationic surfactant is not
simply related to the length of alkyl chain, but there is a
maximum point of toxicity. Dyer et al. have developed the
quantitative structure-activity relationships (QSAR) of
anionic surfactant, alcohol ethoxysulphates (AES), based
on the chronic toxicity to daphnia. This QSAR calculates
the No Effect Observed Concentration (NOEC) of daphnia
by the alkyl chain length and number of mole of ethoxylate
of AES16). A parabolic trend is also observed in this QSAR,
which shows that the most toxic effect of AES to daphnia
occurs at C14 and C15 alkyl chain. This supports that alkyl
chain length is also a key factor determining the toxicity of
mono alkyl cationic surfactants. We have to avoid using the
C14, C16 and C18 alkyl chains for developing the mono
alkyl cationic surfactant compatible with environment.
Based on the relationship between alkyl chain length and
aquatic toxicity of TACs and DMAs, we found that aquatic
toxicity of TAC and DMA with C22 alkyl chain is relatively
less toxic than other alkyl chains. These trends indicate
that C22 alkyl chain is compatible with the aquatic toxicity.
Though there is not many data, the acute toxicity of DMA22 to daphnia tends to be less toxic than TAC-22, which
indicates that toxicological compatibility of DMA is better
than TAC. The toxicity of APA-18 to algae and fish shows
the same order of toxic values of DMA-18. It suggests that
the combination of C18 alkyl chain and amidopropyl functional group is not an effective structure for reducing the
toxicity. On the other hand, APA-22 is less toxic than APA18 by two orders of magnitude and all toxicity values of
APA-22 to algae, daphnia and fish are over 1 mg/L. As discussed in biodegradation trend, we found that the combination of long alkyl chain and amidopropyl functional group
is also very important structure to reduce the aquatic toxicity.
4.3 Possible biodegradation pathway of APA-22
To investigate the biodegradation pathway of APA-22,
structure of intermediate is determined by 1H-NMR analysis, and residual organic matters are measured by DOC

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J. Oleo Sci. 57, (10) 529-538 (2008)

Aquatic Toxicity and Biodegradability of Advanced Cationic Surfactant APA-22

analysis. Figure 3 shows the 1H-NMR chart of APA-22 dissolved in the CDCl3, 5-day and 19-day samples dissolved in
CD3OD. In the standard solution without inoculums, typical proton signals of C22 alkyl chain, amidopropyl, methyl
of amine and lactic acid salt are observed. In 5-day sample,
APA-22, fatty acid and N,N-dimethyl-1,3-propanediamine
(DMAPA) are clearly detected, while lactic acid is disappeared completely. This suggests that hydrolysis occurred
between fatty acid and DMAPA in the primary biodegradation process. This kind of cleavage has been also reported
in biodegradation pathway of di-long-chain tertiary amine

Fig. 3

salt3). In 19-day sample, APA-22 and fatty acid have completely disappeared, and only DMAPA is observed. Residual organic matters (DOC) originated from APA-22 decrease
gradually and disappear at 28-day, which indicates that
APA-22 and its intermediates are completely removed from
tested river water during the test periods (Fig. 4). We have
estimated the possible route of biodegradation pathway of
APA-22 as shown in Fig. 5. In the primary stage, APA-22 is
separated into two intermediates by hydrolysis. One is
fatty acid and the other is DMAPA. After hydrolysis, fatty
acid is mineralized to CO2 and H2O through the omega and

H-NMR Chart of Standard Solution, 5-day Sample and 19-day

Sample.
Small alphabetical letters denote the each proton signal for APA-22
and lactic acid. Capital letters and numerals also denote each proton
signals for fatty acid and DMAPA.
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M. Yamane, T. Toyo, K. Inoue et al.

Fig. 4 Dissolved Organic Carbon (DOC) Profile of

Residue Organic Matter Originated from APA-22 in
Biodegradation Test Using River Water.

Fig. 5 Estimated Biodegradation Pathway of APA-22.

This pathway is estimated from 1H-NMR and DOC analysis.

beta-oxidation process. DMAPA is also mineralized to CO2,

H2O, NH3, and NO2 (or NO3). Investigating the biodegradation test of APA-22 using river water, we observed the disappearance of APA-22 and its intermediates during the test
period.
4.4 Environmental hazardous data of the intermediates
originated from APA-22
The toxicity of APA-22 to of algae, daphnia and fish is
over 1 mg/L (Table 4), which is relatively less toxic to
aquatic organisms than other mono alkyl cationic surfac-

tants. The aquatic toxicity of some intermediates originated from a degradation of APA-22 is reported. Toxicity of
C22 fatty acid to algae, daphnia and fish is over 5.0 mg/L
and is less toxic than APA-2217). Toxicity of DMAPA to
algae, daphnia and fish is also less toxic than APA-22 and
all toxic values are over 50 mg/L18). Besides, C22 fatty acid
and DMAPA are also reported to be readily biodegradable18,19). According to the above hazardous data of intermediates, it is suggested that there will be a little adverse
effect for environmental risk.

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J. Oleo Sci. 57, (10) 529-538 (2008)

Desmodesmus subspicatus
Daphnia magna
Leuciscus idus
Pseudokirchneriella subcapitata
Daphnia magna
Oryzias latipes

Biodegradation
Algae
Invertebrate
Fish

Biodegradation
Algae
Invertebrate
Fish

Aminopropyl
dimethylamine
(DMAPA)

C22 Fatty acid

Species
Pseudokirchneriella subcapitata
Daphnia magna
Oncorhynchus mykiss

Test type

OECD301C
OECD201
OECD202
OECD203

OECD301D
Algentest in Anlehnung an UBA
EG-Richtlinie 78/83/EGW
DIN 38412

OECD301B
ECETOC T.D. No 28
OECD201
OECD202
OECD203

Protocol

Biodegradability and Aquatic Toxicity of APA-22 and Its Intermediates.

Aerobic biodegradation
Anaerobic biodegradation
Algae
Invertebrate
Fish

APA-22

Test substance

Table 4

52% (Readily biodegradable)

>5.0 mg/L
>5.0 mg/L
>5.0 mg/L

69% (Readily biodegradable)

56.2 mg/L
59.5 mg/L
122 mg/L

100% (passed the 10 day-window)

100%
2.1 mg/L
1.4 mg/L
6.6 mg/L

Result and LC50/EC50

Aquatic Toxicity and Biodegradability of Advanced Cationic Surfactant APA-22

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M. Yamane, T. Toyo, K. Inoue et al.

5 CONCLUSIONS
On the basis of the relationship between environmental
properties (biodegradation and aquatic toxicity) and structural characteristics (alkyl chain length and intermediate
functional group) of TACs, DMAs and APAs, we have
developed the advanced mono alkyl cationic surfactant,
APA-22. APA-22 is easily biodegradable in both of aerobic
and anaerobic conditions. In addition, the toxicity to algae,
daphnia and fish is over 1 mg/L, indicating that APA-22 is
less toxic to aquatic organisms than other mono alkyl
cationic surfactants. The combination of C22 alkyl chain
and amidopropyl functional group is very important for the
enhanced biodegradation and reducing the aquatic toxicity.
Besides, intermediates produced in the degradation by
microorganisms are also readily biodegradable and less
toxic than APA-22.

7.

8.

9.

10.

11.

ACKNOWLEDGMENT
We acknowledge for many toxicologists in Safety
Research Laboratories, Kao Corporation. They derived the
environmental data. And we also acknowledge for Mr
Suzuki for useful comments and suggestions.

12.

13.

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