Title of Invention

CLEANSING COMPOSITION

Abstract There is provided a cleansing composition which has creamy foaming and excellent cleansing power, provides no stretched feeling of skin after rinsing and a refreshed feeling of skin, is excellent in storage stability and exhibits no reduction in physical properties, formation of precipitates and yellowing during a long-term storage period by combining N-acyl-aspartic acid or a salt thereof and N-acyl-diaspartic acid or a salt thereof, which have the same molecular structure of the N-acyl group, with a higher fatty acid or a salt thereof which has the same alkyl group as that of the above described N-acyl residue.
Full Text Description
CLEANSING COMPOSITION
Technical Field
The present invention relates to a cleansing composition to be used for the
body.
Background Art
Alkyl sulfonates, alkyl ether sulfonates, higher fatty acid salts and the like
have been used as surface active agents for cleansing compositions. However,
milder raw materials have been desired since conventional surface active agents have
had a problem in the irritation to hand skin. In recent years, amino acid-based
surface active agents such as N-acyl glutamates have attracted attention as a surface
active agent which is mild to hand skin and high in safety, and has good
biodegradability.
However, N-acyl glutamates exhibit weak foaming and often provide slimy
and greasy feelings after rinsing. In addition, although alkaline cleansing
compositions containing higher fatty acid salts as a main component provide a
refreshed feeling, there was a problem in the feeling upon use like a stretched feeling
of the skin after use thereof.
In order to solve these problems, Japanese Patent Laid-Open No. 2-268114
(Patent Document 1) has attempted to improve sliminess and foaming by defining a
neutralized salt of an N-acyl aspartic acid, but as a result of the study by the present
inventors, it has been found that both a refreshed feeling thereof and improvement of
a stretched feeling after use thereof are still not satisfactory. Japanese Patent
Laid-Open No. 10-121091 (Patent Document 2) discloses a cleansing composition

containing an N-long-chain-acyl dipeptide salt in which the dipeptide moiety is
composed of acidic amino acids and an N-long-chain-acyl acidic amino acid salt, and
discloses that the cleansing composition is non-irritating, has a high resistance to
hard water and provides a pleasant feeling upon use. However, there is no
description on a refreshed feeling, and as a result of the study by the present
inventors, it has been found that the refreshed feeling is not satisfactory and foaming
is also not yet satisfactory. Japanese Patent Laid-Open No. 2003-183152 (Patent
Document 3) discloses a creamy skin cleansing composition containing an N-acyl
acidic amino acid salt, a sulfosuccinic acid surface active agent, a higher fatty acid
salt and polyethylene glycol, and discloses that the composition is excellent in
foaming and the quality of the foam as well as excellent in a feeling upon use.
However, it has been found that a refreshed feeling thereof and foaming are not yet
satisfactory. Japanese Patent Laid-Open No. 2003-171687 (Patent Document 4)
discloses a cleansing composition containing N-acylglutamic acid and a salt thereof,
N-acyldiglutamic acid and a salt thereof and a free fatty acid and a salt thereof,
wherein all components have a common acyl group or an alkylcarbonyl group, and
discloses that the composition is excellent in low-temperature stability and cream
shape retention. However, it has been found that a refreshed feeling and foaming
thereof are not satisfactory and it exhibits a slimy feeling after use.
In addition, Japanese Patent Laid-Open No. 2-268113 (Patent Document 5)
reports that a cleansing agent using N-acyl-aspartic acid or a salt thereof as a base
material among amino acid-based surface active agents has a performance advantage
over those using an N-acyl glutamates because the former provides better foaming
power, more refreshed feeling and better rinsing effect than the latter. However, as
a result of the study by the present inventors, it has been found that when this
cleansing agent is stored at 25°C for a long period of time, there arises a problem of
performance-reduction such as reduction of foaming power, reduction of cleansing

power, disappearance of a refresh feeling and increase of a stretched feeling after
cleansing.
In order to solve these problems, Japanese Patent Laid-Open No. 4-364112
(Patent Document 6) discloses an aqueous liquid cleansing composition containing
an N-(2-hydroxyalkyl)acidicamino acid. However, it describes nothing about a
refreshed feeling, and as a result of the study by the present inventors, it has been
found that the composition provides no refreshed feeling and exhibits a strong
stretched feeling of skin after use. Japanese Patent Laid-Open No. 5-070794
(Patent Document 7) attempts to improve storage stability of a triethanolamine salt
solution of N-acyl-aspartic acid by defining its pH. However, as a result of the
study by the present inventors, it has been found that there is no effect on
improvement in storage stability and the solution exhibits a strong stretched feeling
of the skin after use. Japanese Patent Laid-Open No. 4-180999 (Patent Document
8) attempts to improve storage stability of a composition by defining the molar ratio
of N-acyl-aspartic acid to ethanolamine. However, as a result of the study by the
present inventors, it has been found that the composition exhibits poor foaming and
does not exhibit a satisfactory refreshed feeling.
In the case of using an N-long-chain-acylamino acid salt, in particular sodium
salt or potassium salt, insolubles have often precipitated when an aqueous solution of
the N-long-chain-acylamino acid salt is stored at a low temperature. In addition,
when an N-long-chain-acylamino acid salt and its aqueous solution are stored at a
high temperature, the N-long-chain-acylamino acid salt and its aqueous solution have
often discolored to yellow. Therefore, there have been problems in that they need
extra work of redissolution or filtration when they are formulated into a final product,
or the final product discolors to yellow. Thus, an N-long-chain-acyl amino acid salt
and its aqueous solution excellent in low and high temperature stability have been
demanded.

In order to improve low-temperature stability, for example, Japanese Patent
Laid-Open No. 2001-131129 (Patent Document 9) discloses the improvement of
low-temperature stability by combining an N-long-chain-acylamino acid salt with a
hydrophilic substance having 12 or more carbon atoms. However, as a result of the
study by the present inventors, it has been found that although improvement of
low-temperature stability is significant, high-temperature stability is not satisfactory,
because the composition has exhibited yellowing in the evaluation of stability thereof
at 50°C for about one month. Japanese Patent Laid-Open No. 9-78085 (Patent
Document 10) attempts to improve high-temperature stability by combining a
glycine derivative with a metal chelating agent and an antioxidant. However, as a
result of the study by the present inventors, it has been found that insolubles
precipitate at 0°C, showing unsatisfactory low-temperature stability.
Patent Document 1: Japanese Patent Laid-Open No. 2-268114
Patent Document 2: Japanese Patent Laid-Open No. 10-121091
Patent Document 3: Japanese Patent Laid-Open No. 2003-183152
Patent Document 4: Japanese Patent Laid-Open No. 2003-171687
Patent Document 5: Japanese Patent Laid-Open No. 2-268113
Patent Document 6: Japanese Patent Laid-Open No. 4-364112
Patent Document 7: Japanese Patent Laid-Open No. 5-070794
Patent Document 8: Japanese Patent Laid-Open No. 4-180999
Patent Document 9: Japanese Patent Laid-Open No. 2001-131129
Patent Document 10: Japanese Patent Laid-Open No. 9-78085
Disclosure of the Invention
It is an object of the present invention to provide a cleansing composition
which has creamy foams, is excellent in foaming and exhibits excellent cleansing

power; which is excellent in the feeling upon use in that it provides a refreshed
feeling after rinsing and provides no stretched feeling of the skin after cleansing; and
in which it can be stored for a long period of time under an acidic condition at 25°C
and when the pH is returned to weakly acidic after the long storage, all of the
above-described performance are reproduced, particularly exhibiting a high foaming
power property that is the same as that of the composition before the long storage,
and to provide a cleansing composition which does not form precipitates at a low
temperature in a state of an aqueous solution, and which is resistant to yellowing at a
high temperature in a state of an aqueous solution and in a solid state.
As a result of extensive study to solve the above problems, the present
inventors have discovered that a cleansing composition in which the above problems
are solved can be obtained by combining N-acyl-aspartic acid or a salt thereof and
N-acyl-diaspartic acid or a salt thereof, which have the same molecular structure of
the alkyl group for the N-acyl group with a higher fatty acid or a salt thereof which
has the same alkyl group as that of the above described N-acyl group. The finding
has led to the completion of the present invention.
The present invention includes the following inventions from 1 to 30.
1. A cleansing composition, comprising:
(A) N-acyl-aspartic acid or a salt thereof represented by formula (1):
[Formula 1]


wherein R is an alkyl group having from 7 to 23 carbon atoms, and M1 and M2 are
each, independently, a hydrogen atom, an alkali metal, an alkaline earth metal,
ammonium, alkylammonium, alkanolammonium or a protonated basic amino acid;
(B) N-acyl-diaspartic acid or a salt thereof, represented by formula (2):
[Formula 2]

wherein R is the same alkyl group specified in formula (1), and M3, M4 and M5 are
each, independently, a hydrogen atom, an alkali metal, an alkaline earth metal,
ammonium, alkylammonium, alkanolammonium or a protonated basic amino acid;
or represented by formula (3):
[Formula 3]

wherein R is the same as in formula (2), and M6, M7 and M8 are each, independently,
a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium,
alkylammonium, alkanolammonium or a protonated basic amino acid; and

(C) a higher fatty acid or a salt thereof represented by formula (4):
[Formula 4]

wherein R is the same as in formula (2), and M9 is a hydrogen atom, an alkali metal,
an alkaline earth metal, ammonium, alkylammonium, alkanolammonium or a
protonated basic amino acid.
2. The cleansing composition according to invention 1, wherein component (B)
comprises N-acyl-diaspartic acid or a salt thereof represented by formula (2) and
N-acyl-diaspartic acid or a salt thereof represented by formula (3).
3. The cleansing composition according to invention 2, wherein the weight ratio
of N-acyl-diaspartic acid or a salt thereof represented by formula (2) to
N-acyl-diaspartic acid or a salt thereof represented by formula (3) is 1:3 to 3:1.
4. The cleansing composition according to invention 3, wherein the amount of
component (B) is 0.1 to 15% by mass based on the total amount of components (A)
and (B), and the amount of component (C) is 0.1 to 15% by mass based on the total
amount of components (A) and (C).
5. The cleansing composition according to invention 4, wherein the amount of
component (B) is 0.1 to 8% by mass based on the total amount of components (A)
and (B), and the amount of component (C) is 0.1 to 10% by mass based on the total
amount of components (A) and (C).
6. The cleansing composition according to any of inventions 1 to 5, wherein the
composition has a pH of from 5.0 to 7.0.
7. The cleansing composition according to any of the inventions 1 to 6, wherein
R in component (A) has from 9 to 17 carbon atoms.

8. The cleansing composition according to any of inventions 1 to 7, wherein M1
to M9 in formulas (1) to (4) are one or more selected from a hydrogen atom, sodium,
lithium, potassium, ammonium and triethanolammonium.
9. The cleansing composition according to invention 8, wherein M1 to M9 in
formulas (1) to (4) are only one selected from sodium, lithium, potassium,
ammonium and triethanolammonium, other than a hydrogen atom.
10. The cleansing composition according to invention 9, wherein M1 to M9 in
formulas (1) to (4) are selected only from a hydrogen atom and sodium.
11. A cleansing composition comprising component (A) represented by formula
(1), wherein after the composition is stored at 50°C for 30 days, the reduction in
foaming power thereof is 20% or less.
12. The cleansing composition according to invention 11, wherein after the
composition is stored at 50°C for 30 days, the increase in the content of a free fatty
acid based on component (A) is 15% by mass or less.
13. The cleansing composition according to invention 11 or 12, further
comprising component (B) which comprises N-acyl-diaspartic acid or a salt thereof
represented by formula (2) and N-acyl-diaspartic acid or a salt thereof represented by
formula (3).
14. The cleansing composition according to invention 13, wherein the weight
ratio of N-acyl-diaspartic acid or a salt thereof represented by formula (2) to
N-acyl-diaspartic acid or a salt thereof represented by formula (3) is 1:3 to 3:1.
15. The cleansing composition according to invention 13 or 14, wherein the
amount of component (B) is 0.1 to 15% by mass based on the total amount of
components (A) and (B).
16. The cleansing composition according to any of inventions 11 to 15, further
comprising component (C) represented by formula (4).

] 7. The cleansing composition according to invention ] 6, wherein the amount of
component (C) is 0.1 to 1.5% by mass based on the total amount of components (A)
and (C).
18. The cleansing composition according to any of inventions 11 to 17, wherein
the composition has a pH of from 4.5 to 6.0.
19. The cleansing composition according to any of inventions 11 to 18, further
comprising component (D) which comprises one or more selected from inorganic
salts and organic acid alkali metal salts, wherein the amount of component (D) is
from 0.01 to 50% by mass based on the amount of component (A).
20. A method for producing a cleansing composition of invention 1 in which
N-acyl-aspartic acid or a salt thereof is used as component (A), wherein the
N-acyl-aspartic acid or a salt thereof is prepared by the steps comprising:
adjusting the N-acyl-aspartic acid or a salt thereof to a pH of 6.0 or higher;
and then
adjusting the resulting mixture to a final pH of from 4.5 to 6.0,
wherein the difference between the highest pH and the final pH is 0.5 or more.
21. A cleansing composition characterized in that the composition comprises
component (A) represented by formula (1) which is neutralized to a pH in the range
of from 6.6 to 10; after the composition is stored at 50°C for 30 days, the reduction
in foaming power thereof in a weakly acidic region is 10% or less; and the reduction
in the measured value of visible-light transmittance at a wavelength of 430 nm is
10% or less.
22. The cleansing composition according to invention 21, comprising component
(A) represented by formula (1), component (B) represented by formula (2) or (3), and
component (C) represented by formula (4).

23. The cleansing composition according to invention 22, wherein component (B)
comprises N-acyl-diaspartic acid or a salt thereof represented by formula (2) and
N-acyl-diaspartic acid or a salt thereof represented by formula (3).
24. The cleansing composition according to invention 23, wherein the weight
ratio of N-acyl-diaspartic acid or a salt thereof represented by formula (2) to
N-acyl-diaspartic acid or a salt thereof represented by formula (3) is 1:3 to 3:1.
25. The cleansing composition according to any of inventions 22 to 24, wherein
the amount of component (B) is 0.1 to 15% by mass based on the total amount of
components (A) and (B), and the amount of component (C) is 0.1 to 15% by mass
based on the total amount of components (A) and (C).
26. The cleansing composition according to any of inventions 21 to 25, wherein
the content of the component (A) in which the alkyl group in formula (1) has 11
carbon atoms is 50% by mol or more of the total component (A).
27. The cleansing composition according to any of inventions 21 to 26, wherein
M1 and M2 in formula (1) are each an alkali metal salt in addition to a hydrogen
atom.
28. The cleansing composition according to invention 27, wherein M1 and M2 in
formula (1) are each sodium in addition to a hydrogen atom.
29. The cleansing composition according to any of inventions 1 to 28, comprising
from 0.005 to 0.3 part by mass of phosphorus.
30. The cleansing composition according to any of inventions 1 to 28, comprising
from 0.005 to 0.08 part by mass of organic phosphorus.
Best Mode for Carrying Out the Invention
The present invention will be specifically described below.
Component (A) in the cleansing composition of the present invention is
N-acyl-aspartic acid or a salt thereof represented by the above formula (1), wherein

optical activity of the amino acid moiety thereof may be L-furm, D-form or
DL-form.
Component (B) in the cleansing composition of the present invention is
N-acyl-diaspartic acid or a salt thereof represented by the above formula (2) or (3),
wherein optical activity of the amino acid moiety thereof may be L-form, D-form or
DL-form. The mass ratio of the N-acyl-diaspartic acid or a salt thereof represented
by formula (2) to the N-acyl-diaspartic acid or a salt thereof represented by formula
(3) in component (B) is not particularly limited, but preferably both types of the
N-acyl-diaspartic acids or salts thereof are present, more preferably the mass ratio is
1:3 to 3:1, in which the composition exhibits the highest foaming power. The
amount of component (B) in the cleansing composition is not particularly limited, but
it is preferably 0.1 to 15% by mass based on the total amount of components (A) and
(B). When the amount is less than 0.1% by mass, a refreshed feeling after cleansing
cannot be sufficiently obtained depending on an additive contained in the
composition. When the amount is higher than 15% by mass, foaming may be
reduced depending on an additive contained in the composition, resulting in
disadvantage in terms of cost such as raw material cost. The amount of component
(B) in the cleansing composition is more preferably 0.1 to 8% by mass.
Component (C) in the cleansing composition of the present invention is a
higher fatty acid or a salt thereof represented by formula (4). Examples of
component (C) include higher fatty acids such as caprylic acid, capric acid, lauric
acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachic acid, behenic
acid, undecylenic acid, palmitoleic acid, oleic acid, linoleic acid, Iinolenic acid,
oxystearic acid, recinoleic acid, lanolin fatty acid, coconut oil fatty acid, castor oil
fatty acid, olive oil fatty acid, palm oil fatty acid and palm kernel oil fatty acid, and
salts thereof including sodium salts, potassium salts, lithium salts, magnesium salts,
calcium salts, ammonium salts, alkylammonium salts, monoethanolamine salts,

diethanolamine sails, tricthanolamine salts, aminomethyl propanol salts, lysine salts.
arginine salts and the like. It is also possible to independently formulate a higher
fatty acid and a base instead of formulating a salt, resulting in formation of a salt in
the system. The higher fatty acid or a salt thereof may be used singly or in
combination of two or more. The amount of component (C) in the composition is
not particularly limited, but it is preferably 0.1 to 15% by mass based on the total
amount of components (A) and (C). Depending on an additive contained in the
composition, a refreshed feeling after cleansing cannot be sufficiently obtained when
the amount is less than 0.1% by mass. When the amount is higher than 15% by
mass, foaming may be insufficient and a stretched feeling may develop after
cleansing. The amount of component (C) in the composition is more preferably 0.1
to 10% by mass.
In the present invention, all of the N-acyl groups in components (A) and (B)
and component (C) have the same alkyl group. When any of the alkyl groups in
these three components are not the same, foaming by the cleansing agent may be
reduced and a stretched feeling after cleansing may develop.
The alkyl group contained in the N-acyl group of component (A) preferably
has from 7 to 23 carbon atoms. When it has less than 7 or more than 23 carbon
atoms, a foaming power may be reduced depending on an additive contained in the
composition. The alkyl group preferably has from 9 to 17 carbon atoms, and more
preferably the content of the component (A) in which the alkyl group has 11 carbon
atoms is 50% by mol or more of the total component (A).
The cleansing composition of the present invention can be produced and used
in a relatively wide pH region, but it is preferred that the pH be adjusted in a range of
4.5 to 7.0. Depending on an additive contained in the composition, foaming may be
reduced when the pH is less than 4.5 or higher than 7.0. The pH is more preferably
from 5.0 to 6.5.

The cleansing composition of the present invention may comprise one or
more selected from inorganic salts and organic acid alkali metal salts as component
(D). Examples of the inorganic salts include sodium chloride, potassium chloride,
magnesium chloride, sodium sulfate, potassium sulfate, magnesium sulfate, sodium
nitrate and the like. Examples of the organic acid alkali metal salts include the
sodium salt of pyrrolidone carboxylic acid, sodium lactate, sodium citrate, sodium
malate, sodium tartrate, sodium adipate, monosodium glutamatc, sodium aspartate,
sodium maleate, sodium fumarate, sodium acetate, sodium glycolate and the like.
The amount of component (D) in the composition is preferably 0.01 to 50% by mass
based on component (A). Depending on an additive contained in the composition,
storage stability at 25°C may be impaired when the amount is less than 0.01 % by
mass. When the amount is 50% by mass or more, foaming may be insufficient.
The amount of component (D) in the composition is more preferably 0.01 to 30% by
mass.
The cleansing composition of the present invention is preferably a
composition in which after the composition is stored at 50°C for 30 days, the
reduction in foaming power thereof is 20% or less. An example of the cleansing
composition of the present invention may include a composition prepared by using
component (A) treated under a specific condition as a raw material. That is, the
N-acyl-aspartic acid salt is first treated with sodium hydroxide, potassium hydroxide,
ammonia, magnesium hydroxide, monoethanolamine, diethanolamine,
triethanolamine or the like preferably to a pH of 6.0 or higher, more preferably to a
pH of 7.0 or higher. Then, the resulting mixture is treated with hydrochloric acid,
sulfuric acid, nitric acid, acetic acid, citric acid or the like to a final pH of from 4.5 to
6.0. During the treatment, the difference between the highest pH and the final pH is
controlled to be 0.5 or more. The N-acyl-aspartic acid or a salt thereof subjected to
the above-described treatment can be used as component (A). In this production

example, when pH is not increased to 6.0 or higher, the reduction in foaming power
after the composition is stored at 50°C for 30 days may not be 20% or less. When
pH is not adjusted to the range between 4.5 and 6.0 during the reduction of pH,
foaming may be insufficient. Moreover, when the difference between the highest
pH and the final pH is less than 0.5, the cleansing agent may not provide sufficient
storage stability.
As described herein the term "foaming power" refers to a measured value
obtained by measuring 300 g of a liquid sample having a concentration of 0.33% by
the Osterizer method. When it is mentioned that after the composition is stored at
50°C for 30 days the reduction in foaming power thereof is 20% or less, the
reduction in the measured value is 20% or less.
The cleansing composition of the present invention is preferably a
composition in which after it is stored at 50°C for 30 days, the increase in the content
of a free fatty acid based on component (A) is 15% by mass or less
Here, the free fatty acid is a product formed by the hydrolysis of component
(A). For example, when component (A) is sodium lauroyl aspartate, the free fatty
acid formed by the hydrolysis of component (A) is lauric acid.
Generally, a cleansing composition containing component (A) has a tendency
that hydrolysis of component (A) proceeds when the composition is stored for a long
period of time in a heated state, leading to increase in the content of a free fatty acid.
When the increase in the content can be suppressed to 15% by weight or less relative
to component (A), the composition preferably provides excellent foaming. The
content is more preferably suppressed to 10% by weight or less, most preferably to
8% by weight or less.
An example of a method for suppressing the increase in the content of a free
fatty acid to 15% by weight or less relative to component (A) includes preparing the
cleansing composition of the present invention by using component (A) treated under

a specific condition as a raw material. That is, an aqueous solution of the
N-acyl-aspartic acid salt is first treated with sodium hydroxide, potassium hydroxide,
ammonia, magnesium hydroxide, monoelhanolamine, diethanolamine,
triethanolamine or the like to a pH of 6.0 or higher, preferably to a pH of 7.0 or
higher. Then, the resulting mixture is treated with hydrochloric acid, sulfuric acid,
nitric acid, acetic acid, citric acid or the like to a final pH of from 4.5 to 6.0. During
the treatment, the difference between the highest pH and the final pH is controlled to
be 0.5 or more. The N-acyl-aspartic acid salt subjected to the above-described
treatment can be used as component (A).
Moreover, when the cleansing composition of the present invention is stored
in a liquid form, the pH thereof is preferably higher than 6.5 and is preferably 10 or
less. When the pH is 6.5 or less, the reduction in foaming power after the
composition is stored at 50°C for 30 days is larger than 10%. When the pH is
higher than 10, the reduction in foaming power after the composition is stored at
50°C for 30 days is small, but significant yellowing of the liquid is apparent. In
particular, when the pH is in the range of 7.0 to 9.0, the reduction in foaming power
after the composition is stored at 50°C for 30 days is smaller and the yellowing
hardly occurs, which is more preferable. As described herein the term "yellowing"
refers to a value measured as the degree of reduction in visible-light transmittance at
a wavelength of 430 nm by using a spectrophotometer.
Phosphorus in the present invention includes phosphorus compounds,
including organic phosphorus, such as phosphoric acid and phosphorous acid,
sodium phosphate, polyphosphates, metaphosphates, lecithins, phytic acid or salts
thereof, alkyl phosphates and salts thereof such as magnesium ascorbyl phosphate,
ascorbyl phosphates, sodium lauryl phosphate, sodium myristyl phosphate and
sodium coconut oil fatty acid phosphate, alkyl phosphate triethanolamine ethers such
as myristyl phosphate triethanolamine ether, polyoxyethylene alkyl ether phosphoric

acids and salts thereof such as sodium polyoxycthylene lauryl ether phosphate,
sodium polyoxyethylenc cetyl ether phosphate and sodium polyoxyethylene oleyl
ether phosphate, and phosphonic acid. The content of phosphorus is not
particularly limited, and may be of any concentration in the range of from 0.005 to
0.3% by mass. When the content of phosphorus is less than 0.005% by mass, the
composition may be discolored yellow during the storage thereof at high
temperatures. When the content of phosphorus is higher than 0.3% by mass, the
composition may be cloudy or may precipitate at low temperatures. The content of
phosphorus is more preferably from 0.005 to 0.08% by mass, most preferably from
0.05 to 0.08% by mass.
The content of organic phosphorus in the present invention is not particularly
limited, and may be of any concentration in the range of from 0.005 to 0.08% by
mass. Preferably, it is from 0.005 to 0.05% by mass. When the content of organic
phosphorus is less man 0.005% by mass, the composition may be discolored yellow
during the storage thereof at high temperatures. When the content of phosphorus is
higher than 0.08% by mass, the composition may be cloudy or may precipitate at low
temperatures. The content of organic phosphorus is more preferably from 0.01 to
0.05% by mass. As described herein the term "content of organic phosphorus"
refers to the content of phosphorus contained in the soluble fraction in diethyl ether
when the cleansing composition is fractionated by adding it into a mixture of diethyl
ether/distilled water under an acidic condition by sulfuric acid.
The content of the above described phosphorus and organic phosphorus can
be adjusted by using raw materials having a specific content of phosphorus and
controlling temperatures in the step for producing component (A) or (B) of the
present invention.
Various components generally used as cosmetics can be optionally mixed
with the cleansing composition of the present invention depending on the purpose

thereof, the amount of these components being in the range they do not impair the
effect of the cleansing composition.
Examples of the optional components to be mixed with the cleansing
composition of the present invention may include the followings:
powder components such as calcium carbonate, ta!c, mica, lauroyllysine,
titanium dioxide and zinc dioxide; natural animal/plant oils and fats such as jojoba
oii, macadamia mil oil, avocado oil, evening primrose oil, mink oil, rapeseed oil,
castor oil, sunflower oil, corn oil, cacao oil, coconut oil, rice bran oil, olive oil,
almond oil, sesame oil, saffiower oil, soybean oil, camellia oil, persic oil, castor oil,
mink oil, cottonseed oil, Japan wax, palm oil, palm kernel oil, egg yolk oil, lanolin
and squalene;
synthesized triglycerides; hydrocarbons such as squalane, liquid paraffin,
Vaseline, ceresin, macrocrystalline wax and isoparaffin;
waxes such as carnauba wax, paraffin wax, spermaceti, beeswax, candelilla
wax and lanolin;
higher alcohols such as cetanol, stearyl alcohol, lauryl alcohol, cetostearyl
alcohol, oleoyl alcohol, behenyl alcohol, lanolin alcohol, hydrogenated lanolin
alcohol, hexyl decanol and octyl dodecanol;
cholesterol and derivatives thereof such as cholesteryl-octyldodecyl-behenyl;
esters such as isopropyl myristate, isopropyl palmitate, isopropyl stearate,
glycerol-2-ethylhexanoate and butyl stearate;
polar oils such as diethylene glycol monopropyl ether, polyoxyethylene
polyoxypropylene pentaerythritol ether, polyoxypropylene butyl ether and ethyl
linolate;
silicones, including various derivatives, such as amino-modified silicones,
epoxy-modified silicones, carboxyl-modified silicones, carbinol-modified silicones,
carpinol-modified silicones, methacryl-modified silicones, mercapto-modified

silicones, phenol-modified silicones, one-side terminal reactive silicones, dissimilar
functional group-modified silicones, polyether-modified silicones,
methylstyryl-modified silicones, alkyl-modified silicones, higher fatty acid
ester-modified silicones, hydrophilic special modified silicones, higher
alkoxy-modified silicones, higher fatty acid-containing silicones and
fluorine-modified silicones, more specifically, silicone resins,
methylphenylpolysiloxane, methylpolysiloxane, octamethylcyclotetrasiloxane,
decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane,
methylcyclopolysiloxane, octamethyltrisiloxane, decamethyltetrasiloxane,
polyoxyethylene-methylpolysiloxane copolymers,
polyoxypropylene-methylpolysiloxane copolymers,
poly(oxyethylene-oxypropylene)methylpolysiloxane copolymers,
methylhydrogenpolysiloxane, tetrahydrotetramethylcyclotetrasiloxane,
stearoxymethylpolysiloxane, cetoxymethylpolysiloxane, methylpolysiloxane
emulsion, high polymeric methylpolysiloxane (1) and (2), trimethylsiloxysilicate,
crosslinked methylpolysiloxane, crosslinked methylphenylpolysiloxane and
crosslinked methylphenylpolysiloxane (2);
ultraviolet absorbers such as p-aminobenzoic acid and derivatives thereof,
p-methoxy cinnamic acid derivatives such as homomethyl-7N-acetylanthranylate,
butyl methoxybenzoylmethane, mono-2-ethylhexanoic glyceryl diparamethoxy
cinnamate and octyl cinnamate, salicylic acid derivatives such as amyl salicylate,
benzophenone derivatives such as 2,4-dihydroxybenzophenone, ethylhexyl
dimethoxybenzylidene dioxoimidazoline propionate, liquid lanolin acetate,
Scutellaria baicalensis root extract and trianilino-p-carboethylhexyloxy-triazine;
skin-whitening components such as ascorbic acid and derivatives thereof such
as arbutin and kojic acid, glutathione, glycyrrhiza extract, clove extract, tea extract,

astaxanthin, bovine placenta extract, tocopherol and derivatives thereof", tranexamic
acid and salts thereof, azulene and γ-hydroxybutyric acid;
******humectants such as polyhydric alcohols such as maltitol, sorbitol, glycerin,
propylene glycol, 1,3-butylene glycol, polyethylene glycol and glycols, hyaluronic
acid and salts thereof such as sodium hyaluronate, fermentation metabolites such as
hydrolysates of yeast and yeast extract, yeast culture solution and lactic acid bacteria
culture solution, water soluble proteins such as collagen, elastin, keratin and sericin,
peptides and salts thereof such as collagen hydrolysates, casein hydrolysates, silk
hydrolysates and sodium polyaspartate, carbohydrates/ polysaccharides and
derivatives thereof such as trehalose, xylobiose, maltose, sucrose, raffinose, glucose
and plant mucopolysaccharides, amino acids such as water soluble chitins, chitosan,
pectin, chondroitinsulfuric acid and salts thereof, glycosaminoglycan and salts
thereof, glycine, serine, threonine, alanine, aspartic acid, tyrosine, valine, leucine,
arginine, glutamine and proline, sugar amino acid compounds such as aminocarbonyl
reaction products, extracts of plants such as aloe and marronnier, trimethylglycine,
urea, ammonia, lanoline, squalane, squalene, glucosamine, creatinine, nucleic acid
related substances such as DNA and RNA;
thickeners such as carboxymethylcellulose, hydroxyethylcellulose,
hydroxypropyltrimethylammonium chloride ether, ethylcellulose,
hydroxypropylcellulose, methylhydroxypropylcellulose, soluble starch,
carboxymethyl starch, methyl starch, propylene glycol alginate, polyvinyl alcohol,
polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl polymers, polyacrylic
acid, methylcellulose, hydroxyethylcellulose, gum arabic, xanthan gum, guar gum,
locust bean gum, quince seed, carrageenan, galactan, pectin, mannan, starch, dextran,
succinoglucan, curdlan, hyaluronic acid, gelatin, casein, albumin, collagen,
methoxyelhylene-maleic anhydride copolymers, amphoteric methacrylate
copolymers, polydimelhylmethylenc piperidinium chloride, polyacrylate copolymers,

polyvinyl acetate, nitrocellulose, silicone resins, polyoxyethylene fatty acid esters
such as polyethylene glycol fatty acid esters and polyethylene glycol distearate,
polyoxyethylene fatty acid ester methyl glycosides such as polyoxyethylene methyl
diolcate glucoside and α-olefin sulfonic acid such as tetradecene sulfonic acid;
metal ion blocking agents such as ethylenediaminetetraacetic acid and salts
thereof, hydroxyethylenediaminetriacetic acid and salts thereof, ascorbic acid,
succinic acid and gluconic acid;
organic solvents such as ethanol, propylene glycol and 1,3-butylene glycol;
antioxidants such as butylhydroxytoluene and tocopherol;
antibacterial/antiseptic agents such as benzoic acid and salts thereof, salicylic
acid and salts thereof, sorbic acid and salts thereof, p-oxybenzoic acid alkyl esters
(such as ethylparaben and butylparaben) and salts thereof, dehydroacetic acid and
salt thereof, p-chlorometacresol, hexachlorophene, boric acid, resorcin, tribromsalan,
o-phenylphenol, chlorhexidine gluconate, thiram, photosensitive element No. 201,
phenoxy ethanol, benzalkonium chloride, benzethonium chloride, halocarban,
chlorhexidine hydrochloride, trichlorocarbanilide, tocopherol acetate, zinc pyrithione,
hinokitiol, phenol, isopropylmethylphenol, 2,4,4-trichloro-2-hyroxyphenol and
hexachlorophene;
organic acids such as citric acid, malic acid, tartaric acid, lactic acid, adipic
acid, glutamic acid, aspartic acid, maleic acid, glycol acid and fumaric acid;
vitamin A and derivatives thereof, and vitamin Bs such as vitamin B6
hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate and vitamin B2 and
derivatives thereof;
vitamin Cs such as ascorbic acid and ascorbic acid sulfate; vitamin Es such as
α-tocopherol, β-tocopherol and γ-tocopherol;
various drugs such as blood circulation promoting agents such as vitamins
such as vitamin Ds, vitamin H and pantothenic acid, nicotinamide, benzyl nicotinate,

γ-orizanol, allantoin. glycyrrhizic acid and derivatives thereof, glycyrrhelic acid salts
and derivative thereof, glycyrrhezic acid salts and derivatives thereof, hinokitiol,
mutidine, bisabolol, eucalyptol, thymol inositol, saponins (such as Quillaja saponin,
azuki saponin and luffa saponin), trancxamic acid, pantothenyl ethyl ether,
ethinylestradiol, cepharantfiin, placental extract, swertia extract, cepharanthin,
vitamin E and derivatives thereof and gamma-orizanol, local stimulants such as
capsicum tincture, ginger tincture, cantharidis tincture and benzyl nicotinate,
nutrients such as various vitamins such as vitamin As, vitamin Bs, vitamin Ds,
vitamin Es, pantothenic acid and vitamin H and amino acids, anti-inflammatory
agents such as glycyrrhetic acid, glycyrrhizic acid derivatives, allantoin, azulene,
aminocaproic acid and hydrocortisone, astringents such as zinc oxide, zinc sulfate,
allantoin hydroxyaluminum, aluminum chloride, zinc sulfocarbolate and tannic acid,
refrigerants such as menthol and camphor, antihistamines, silicone-based substances
such as polymeric silicones and cyclic silicones and antioxidants such as tocopherols,
BHA (butylhydroxyanisole), BHT (dibutylhydroxytoluene), gallic acid and NDGA
(nordihydroguaiaretic acid);
natural extracts obtained by extraction with organic solvents, alcohols,
polyhydric alcohols, water, aqueous alcohols or the like or hydrolysis from
animal/plant/ microorganism and a part thereof such as yeast such as Saccharomyces,
mould, bacteria, bovine placenta, human placenta, human funis, yeast, bovine
collagen, milk-derived protein, wheat, soybean, bovine blood, porcine blood, cock's
comb, camomile, cucumber, rice, shea butter, white birch, tea, tomato, garlic,
hamamelis, rose, luffa, hop, peach, apricot, lemon, kiwi, Houttuynia cordata,
capsicum, Sophora flavescens, Rumex japonicus, Nupharjaponicum, sage, Achillea
millefolium, Malva sylvestris, Cnidium officinale Makino, swertia herd, thyme,
Japanese angelica root, spruce, birch, Equisetum arvense L, luffa, marronnier,
Saxifraga stolonifera, arnica, lily, sagebrush, peony root, aloe, aloevera, Scutellariae

radix, phellodendron bark, Carthami Flos, safflower, Gardeniac Fructus, Lithospenni
Radix, Zizyphi Fructus, Aurantii Nobilis Pericarpium, Ginseng Radix, Coicis Semen,
Coix lacryma-jobi, Gardeniae Fructus and Sawara cypress; coloring matter;
sorbitan fatty acid esters such as sorbitan monolaurate, sorbitan sesquiolcate,
sorbitan trioleate, sorbitan monooleate, sorbitan monostearate, sorbitan tristearatc
and sorbitan monoisostearate, polyoxycthylene sorbitan fatty acid esters such as POE
(polyoxyethylene) sorbitan monolaurate, POE sorbitan monostearate, POE sorbitan
tristearate, POE sorbitan monostearate and POE sorbitan monoisostearate,
polyethylene glycol fatty acid esters such as polyethylene glycol monooleate,
polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene
glycol monooleate, polyethylene glycol distearate, polyethylene glycol dioleate and
polyethylene glycol diisostearate; polyoxyethylene alkyl ethers such as POE lauryl
ether, POE cetyl ether, POE stearyl ether, POE oleyl ether and POE behenyl ether;
polyglycerin fatty acid esters such as diglyceryl monostearate, diglyceryl
monooleate, diglyceryl dioleate, diglyceryl monoisostearate, tetraglyceryl
monostearate, tetraglyceryl tristearate, tetraglyceryl pentastearate, hexaglyceryl
monolaurate, hexaglyceryl monomyristate, decaglyceryl distearate and decaglyceryl
diisostearate; polyglycol diesters, fatty acid alkanol amides such as coconut oil fatty
acid monoethanolamide, lauroyl monoethanolamide, myristoyl monoethanolamide,
lauroyl diethanolamide, coconut oil fatty acid ethanolamide, lauroyl
isopropanolamide, myristoyl isopropanolamide and coconut oil fatty acid
isopropanolamide, sugar derivatives such as maltitol hydroxy fatty acid ethers,
alkylated polysaccharide, alkyl glucoside and sugar esters;
polyoxyethylene castor oil, polyoxyethylene cured castor oil, propylene
glycol fatty acid esters such as propylene glycol monostearate and self-emulsifiable
propylene glycol monostearate; glycerin fatty acid esters such as glyceryl
monostearate and self-emulsifiable glyceryl monostearate;

nonionic surfactants such as polyoxyethylcne glycerin fatly acid esters such as
POE glyceryl monostearate, polyoxyethylene sorbitol fatty acid esters such as POE
sorbitol hexastearate, POE sorbitol tetrastearate, POE sorbitol tetraoleate and POE
sorbitol monolauratc, POE octyl phenyl ether, POE nonyl phenyl ether, POE
chlorophenyl ether and polyethylene glycol;
cationic surfactants such as alkyl ammonium salts such as lauryl trimethyl
ammonium chloride, cetyl trimethyl ammonium chloride, beef tallow alkyl trimethyl
ammonium chloride, stearyl trimethyl ammonium chloride, behenyl trimethyl
ammonium chloride, dioctyl dimethyl ammonium chloride, distcaryl dimethyl
ammonium chloride, coconut oil alkyl trimethyl ammonium bromide and stearyl
trimethyl ammonium bromide, lanolin-derived quaternary ammonium salts,
benzalkonium chloride, stearyl dimethylbenzyl ammonium chloride, lauryl amine
oxide, coconut oil alkyl amine oxide and stearic acid diethylaminoethyl amide;
anionic surfactants such as lysine laurate, lysine myristate, coconut oil fatty
acid lysine, palm kernel oil fatty acid lysine, arginine laurate, arginine myristate,
coconut oil fatty acid arginine, palm kernel oil fatty acid arginine, fatty acid salts;
alkyl sulfates and salts thereof such as sodium lauryl sulfate, potassium lauryl sulfate,
sodium myristyl-sulfate and potassium myristyl sulfate, alkyl sulfate triethanolamine
ethers and salts thereof such as lauryl sulfate triethanolamine ether and coconut oil
fatty acid alkyl sulfate triethanolamine ether, alkyl sulfonic acid and salts thereof
such as sodium lauryl sulfonate, sodium myristyl sulfonate and sodium coconut oil
alkyl sulfonate, α-olefin sulfonic acid and salts thereof such as sodium dodecene
sulfonate, sodium tetradecene sulfonate, potassium dodecene sulfonate and
potassium tetradecene sulfonate, linear and branched alkylbenzene sulfuric acid and
salts thereof such as linear dodecylbenzene sulfuric acid and salts thereof, linear and
branched alkylbenzene sulfonic acid and salts thereof such as linear dodecylbenzene
sulfonic acid and salts thereof, acyl methyl taurine and salts thereof such as sodium

lauroyl melhyl taurine, sodium myristoyl methyl taurine, sodium coconut oil fatty
acid acyl methyl taurine, potassium lauroyl methyl taurine, potassium myristoyl
methyl taurine, potassium coconut oil fatty acid acyl methyl taurine, lauroyl methyl
taurine triethanolamine, myristoyl methyl taurine triethanolamine and coconut oil
fatty acid acyl methyl taurine triethanolamine, polyoxyethylene alkyl ether sulfuric
acid and salts thereof such as sodium polyoxyethylene lauryl ether sulfate, sodium
polyoxyethylene cetyl ether sulfate and sodium polyoxyethylene oleyl ether sulfate,
ether carboxylic acids and salts thereof such as sodium salts of carboxylated
polyoxyethylene tridecyl ether, lauroyl isethionate, myristoyl isethionate and coconut
oil fatty acid acyl isethionate;
amphoteric surfactants such as acetic acid betaines such as lauryl
dimethylamino acetic acid betaine and coconut oil fatty acid amide propyl
dimethylamino acetic acid betaine, imidazolinium betaines such as alkyl
carboxymethyl hydroxyethyl imidazolinium betaine and alkyl sodium carboxymethyl
carboxyethyl imidazolinium betaine, alkyl betaines such as coconut oil alkyl betaine
and lauryl betaine and bis(stearyl hydroxyethyl imidazoline) chloroacetic acid
complex;
natural surfactants such as lanoline, cholesterol and saponin;
polymeric surfactants such as sodium alginate, starch derivatives and gum
traganth; perfume; purified water; and the like.
Examples
Next, the present invention will be described in more detail by Examples, but
technical ranges and embodiments thereof of the present invention are not limited to
Examples. Methods for determining various physical properties of the cleansing
compositions obtained in Examples and Comparative Examples will be described
below.


Into a mixer (trade name: MX-V1000, manufactured by Matsushita Electric
Industrial Co., Ltd.) were charged 3.3 g of a cleansing composition sample and 296.7
g of purified water, and the mixture was agitated at 25°C for 30 seconds in the mixer.
Immediately after the agitation, the height (mm) of generated foams was measured.
The foaming power was determined by the height with reference to the following
standards. Higher measured values represent higher foaming power.
Criteria for determining the foaming power (evaluation criteria by points)
7 points: foaming power of 185 mm or higher
6 points: foaming power of 180 mm or higher, less than 185 mm
5 points: foaming power of 175 mm or higher, less than 180 mm
4 points: foaming power of 170 mm or higher, less than 175 mm
3 points: foaming power of 165 mm or higher, less than 170 mm
2 points: foaming power of 160 mm or higher, less than 165 mm
1 point: foaming power of less than 160 mm

Cleansing composition samples were used to perform hand cleansing tests on
eight male and female panelists. The feeling upon use was determined for each test
item (foaming, creaminess of foams, refreshed feeling, and stretched feeling) by
calculating the average of evaluation points submitted by the panelists on the basis of
the evaluation criteria by points as described below.
Criteria for determining the feeling upon use (evaluation criteria by points)
7 points: very good
6 points: good
5 points: slightly good
4 points: fair
3 points: slightly bad

2 points: bad
1 point: very bad

Free fatty acids contained in cleansing composition samples were
quantitatively determined by the technique of high performance liquid
chromatography under the following measurement conditions.
Measurement conditions
Column: 150 x 6 mm (trade name : YMC-Pack, ODS-AM, manufactured
by YMC Co., Ltd.)
Eluant: methanol: water: 1,4-dioxane : phosphoric acid = 1000 : 200 :
24.5 :0.31
Flow rate: 0.8 ml/min
Detector: R1 detector

Visible-light transmittance at a wavelength of 430 nm of cleansing
composition samples was measured by a predetermined method by means of a
spectrophotometer (trade name: UV-1200, manufactured by Shimadzu Corporation)
while maintaining the liquid temperature of the samples at 50°C.

In 50 g of purified water was dissolved 0.1 g of an N-long-chain-acylamino
acid salt, and the mixture was prepared to a concentration of 0.2%. The resulting
mixture was used as a sample to determine the phosphorus content in the sample
using an emission analyzer (trade name: P-4010 type ICP, manufactured by Hitachi,
Ltd.) under the following ICP conditions.
ICP conditions
RF output: 1.0 kw
Plasma gas: 16 L/min

Carrier gas: 0.7 L/min
Auxiliary gas: 1.0 L/min
Liquid feed pump: 10 revolutions/min

The organic phosphorus content was determined by using the P-4010 type
ICP emission analyzer (trade name: manufactured by Hitachi, Ltd.). For preparing
a sample, 0.5 g of an N-long-chain-acylamino acid salt and about 1 mL of an
aqueous 1 mol/L NaOH solution were dissolved in purified water, and the mixture
was adjusted to 100 ml. Into a separatory funnel was taken 50 mL of the resulting
mixture, to which 4 mL of sulfuric acid and 50 mL of diethyl ether were added, and
the mixture was shaken for 2 minutes. The resulting mixture was left standing for 1
hour to separate phases, and then an organic phase was taken out to remove diethyl
ether by a rotary evaporator. The residue was dissolved in 5 mL of an aqueous 1
mol/L NaOH solution, to which distilled water was added to obtain 100 mL of a
mixture, and the resulting mixture was used as a sample. Other than these
operations, quantitative determination was performed under the same conditions and
methods as used for determining the phosphorus content as described above.
Obtained values were defined as the organic phosphorus content.

An aqueous solution of an N-long-chain-acylamino acid salt (30% by mass)
was put in a sample bottle as a sample, which was left standing in a low-temperature
chamber at 0°C and -5°C. The liquid state after 30 days was observed and the
low-temperature stability of the sample was determined according to the following
evaluation criteria.
Evaluation criteria
No change in liquid state excellent ("E" in the table)
Give slight turbidity good ("G" in the table)

Give turbidity fair ("F" in the table)
Give coagulation or precipitation bad ("B" in the table)

An aqueous solution of an N-long-chain-acylamino acid salt (30% by mass)
was put in a sample bottle as a sample, which was left standing in an oven at 50°C
and the appearance of the sample after 30 days was observed. In addition,
N-acyl-aspartic acid salt (solid) in a powder form was put in a sample bottle as a
sample, which was left standing in an oven at 50°C and the state of the sample
powder after 30 days was observed. The results of the observations were evaluated
according to the following evaluation criteria to determine the high-temperature
stability of these samples.
Evaluation criteria
Almost no change vs. the initial excellent ("E" in the table)
Exhibit slight yellowing good ("G" in the table)
Exhibit yellowing fair ("F" in the table)
Exhibit significant yellowing bad ("B" in the table)
In the following Examples, the phosphorus content is indicated by the
percentage based on the N-long-chain-acylamino acid salt (in terms of solid).
Examples 1 to 9
The free acids corresponding to components (A) to (C) described in Table 1
were neutralized with sodium hydroxide and mixed in the proportions described in
Table 1 to prepare cleansing compositions having a concentration of 30% by mass.
The compositions had a pH of 5.6.
Physical properties of the resulting cleansing compositions were evaluated by
the above described methods of measurement and tests. The results are shown in

Table 1. The compositions exhibited excellent results in foaming and feelings upon
use.
Comparative Examples 1 to 11
The free acids corresponding to components described in Table 1 were
neutralized with sodium hydroxide and mixed in the proportions described in Table 1
to prepare cleansing compositions having a concentration of 30% by mass.
Physical properties of the resulting cleansing compositions were evaluated by
the above described methods of measurement and tests. The results are shown in
Table 1.
There were no cleansing compositions which satisfied all of the foaming and
feelings upon use.



Example 10, Comparative Example 12
First and second aqueous solutions of pH 5.0 each containing sodium lauroyl
aspartate in an amount of 30% by mass were prepared. The pH of the first sample
was increased to pH 9.5 with sodium hydroxide and then decreased to pH 5.0 with
hydrochloric acid, followed by adjustment of the concentration to 30% by mass.
The second sample was not subjected to any pH treatment.
The foaming power and the content of free fatty acid were determined for the
above solutions immediately after preparation and after stored in an oven at 50°C for
one month by the above described methods of measurement. The results are shown
in Table 2.
When the solution was subjected to pH treatment, the solution after stored at
50°C for one month had a foaming power of 180 mm and a rate of reduction of about
2%. The difference between the content of free fatty acid in the initial solution and
that in the solution after stored at 50°C for one month was 2.36% by mass. When
the solution was not subjected to pH treatment, the solution after stored at 50°C for
one month had a foaming power of 141 mm and a rate of reduction of about 23%.
The difference between the content of free fatty acid in the initial solution and that in
the solution after stored at 50°C for one month was 16.82% by mass.



Examples 11 to 20
Components (A) to (D) described in Table 3 were mixed in the proportion
described in the table and adjusted to a concentration of 30% by mass to prepare
compositions 1 to 10. The resulting compositions had a pH of 5.0.



The compositions 1 to 10 were each used to prepare cleansing foam having
the following composition, which is one of the cleansing compositions, according to
a conventional method. The feeling upon use of the cleansing foam obtained from
each of the compositions was determined by the above described test. The results
are shown in Table 4. The compositions showed excellent results in the foaming,
creaminess of foams and refreshed feeling. Moreover, these feelings upon use were
maintained for one year at 25°C.
Cleansing foam composition (% by mass)
Compositions 1 to 10 28.0
Betaine 1.0
Oleth-20 1.0
Na cocoyl methyl taurine 3.0
PEG-150 4.0
Lauramide DEA 4.0
Glycol distearate 2.0
BG 10.0
water balance



Comparative Examples 13 to 20
Components (A) to (D) described in Table 5 were mixed in the proportion
described in the table and adjusted to a concentration of 30% by mass to prepare
compositions 11 to 18. The resulting compositions had a pH of 5.0.


The compositions 11 to 18 each were used to prepare a cleansing foam having
the following composition, which is one of the cleansing compositions, according to

a conventional method. The feeling upon use of the cleansing foam obtained from
each of the compositions was determined by the above described test. The results
are shown in Table 6. There was no composition which maintained all of the
feelings upon use such as foaming, creaminess of foams and refreshed feeling for
one year at 25°C.
Cleansing foam composition (% by mass)
Compositions 11 to 18 28.0
Betaine 1.0
Oleth-20 1.0
Na cocoyl methyl taurine 3.0
PEG-150 4.0
Lauramide DEA 4.0
Glycol distearate 2.0
BG 10.0
water balance



Examples 21 to 29, Comparative Examples 21 to 23
A standard sample was prepared from an aqueous solution of lauroyl aspartate
by adjusting the p11 thereof to 5.1 using sodium hydroxide and adjusting the solid
content thereof to 30% by mass. The foaming power and visible-light transmittance
of the standard sample were determined by the above described methods of
measurement. Then, sodium hydroxide was used to adjust the pH of the standard
sample to obtain several samples each having a specified pH during storage, and
these samples were stored in an oven at 50°C for one month. After one month, the
visible-light transmittance and the foaming power as an effective component of
0.33% by weight were determined, by the above described methods of measurement,
for the aqueous sodium lauroyl aspartate solution obtained by adjusting the pH of the
stored liquid back to 5.1 using specified acids in Table 7. The results are shown in
Table 7 comparing with the result of the standard sample.



Examples 30 to 37, Comparative Examples 21 to 28
The compositions shown in Tables 8 and 10 were prepared. These
compositions were each used to prepare cleansing foam having the following
composition, which is one of the cleansing compositions, according to a conventional
method. The feeling upon use of the cleansing foam obtained from each of the
compositions was determined by the above described test. The results are shown in
Tables 9 and 11. The examples, in which compositions using the lauroyl aspartate
in Example 23 were used, showed excellent results in the foaming, creaminess of
foams, refreshed feeling and stretched feeling. Moreover, these feelings upon use
were maintained for one year at 25°C.
Cleansing foam composition (% by mass)
Compositions 19 to 34 34.0
Betaine 1.0
Oleth-20 1.0
Na cocoyl methyl taurine 3.0
PEG-150 4.0
Lauramide DEA 4.0
Glycol distearate 2.0
BG 10.0
water 41.0









Examples 38 to 42, Comparative Examples 29 and 30
An aqueous solution of an N-lauroyl-L-aspartate with a sodium counter-ion
was mixed with potassium pyrophosphate, and the phosphorus content and the low
temperature and high temperature stability of the mixture were determined by the
above described methods of measurement and tests. As apparent from Table 12, the
mixture exhibited good low temperature and high temperature stability when the
phosphorus content was in the range of from 0.005 to 0.3% by mass.
Examples 43 and 44, Comparative Examples 31 and 32
An aqueous solution of an N-lauroyl-L-aspartate with a triethanolamine
counter-ion was mixed with phosphonic acid, and the phosphorus content and the
low temperature and high-temperature stability of the mixture were determined by
the above described methods of measurement and tests. As apparent from Table 13,
the mixture exhibited good low temperature and high temperature stability when the
phosphorus content was in the range of from 0.005 to 0.3% by mass.
Examples 45 and 46, Comparative Example 33
An aqueous solution of an N-lauroyl-L-aspartate with a sodium counter-ion
was mixed with potassium pyrophosphate, and the phosphorus content and the high
temperature stability of the mixture were determined by the above described methods
of measurement and tests. As apparent from Table 14, the mixture exhibited good
high temperature stability when the phosphorus content was in the range of from
0.005 to 0.3% by mass.
Examples 47 to 51, Comparative Examples 34 and 35
An aqueous solution of an N-cocoyl-L-aspartate with a sodium counter-ion
was mixed with potassium metaphosphate, and the phosphorus content and the low

temperature and high temperature stability of the mixture were determined by the
above described methods of measurement and tests. As apparent from Table 15, the
mixture exhibited good low temperature and high temperature stability when the
phosphorus content was in the range of from 0.005 to 0.3% by mass.
Examples 52 to 54, Comparative Examples 36 and 37
An aqueous solution of an N-lauroyl-L-aspartate with a sodium counter-ion
was mixed with phytic acid which is an organic phosphorus, and the phosphorus
content and the low temperature and high temperature stability of the mixture were
determined by the above described methods of measurement and tests. As apparent
from Table 16, the mixture exhibited good low temperature and high temperature
stability when the phosphorus content was in the range of from 0.005 to 0.3% by
mass.










Example 55
An aqueous solution of sodium N-lauroyl-L-aspartate was prepared by the
following procedures.
Acylation step
To a mixed solution of 860 g (5.55 mol) of monosodium L-aspartate, 2,978 g
of deionized water, 222 g (5.55 mol) of sodium hydroxide, was added 1049 g of an
aqueous t-butanol solution having a concentration of 80% by mass. To the resulting
solution under ice cooling, while it is being adjusted to a pH of 12 with sodium

hydroxide having a concentration of 25% by mass. 1,210 g (about 5.2 mol,
phosphorus content of 1.0% by mass, and organic phosphorus content of 0.044% by
mass) of Iauroyl chloride was added dropwise in 2 hours, while agitating the solution
with an agitation power of 1.0 kW/m3. After additional agitation for 30 minutes,
1,136 g of an aqueous t-butanol solution having a concentration of 80% by mass was
added, and agitation was continued for another 30 minutes.
Acid-precipitated phase separation step
Sulfuric acid having a concentration of 75% by mass was added dropwise to
the resulting solution to adjust the pH of the solution to 2 and the temperature of the
solution to 45°C. After the completion of the dropping of the sulfuric acid,
agitation was stopped and the solution was left standing for 20 minutes at 45°C.
The solution was separated into an organic phase and a water phase, and from these
phases the organic phase was isolated.
Washing step
To the isolated organic phase (3,651 g), was added the same amount of
t-butanol in a concentration of 20% by mass, and the resulting solution was adjusted
to 45 °C and agitated for 20 minutes. After stopping agitation, the solution was left
standing for 20 minutes at 45°C, resulting in separation of the solution into an
organic phase and a water phase.
Solvent evaporating step
The organic phase was isolated, and sodium hydroxide was added to the
organic phase so that 83% of the carboxyl group in N-lauroyl-L-aspartic acid in the
organic phase was in the form of salt, and ionized water was added to the resulting
solution so that the solution had a solid content of 30% by mass, followed by mixing
by agitation.
Then, the solution was subjected to vacuum distillation using a 10-L glass
vessel under a pressure of 300 mmHg while adding deionized water so that the solid

content of 30% by mass was maintained during the distillation. After 11 hours from
the start of the distillation, the solution temperature reached 70°C and the distillation
was stopped, obtaining an aqueous solution of sodium N-lauroyl-L-aspartate. The
aqueous solution had a solid content of 30% by mass, and as a result of
dctennination by the above described methods of determination, it was found that the
aqueous solution had a phosphorus content of 0.059% and an organic phosphorus
content of 0.033%, based on the solid content.
The results of the low-temperature stability test (-5°C) and the
high-temperature stability test for the aqueous solution of sodium
N-lauroyl-L-aspartate obtained here were both "excellent".
Example 56
An aqueous solution of sodium N-lauroyl-L-aspartate was obtained by the
same operation as in Example 55 except that the solution temperature in the
acid-precipitated phase separation step and the washing step in Example 55 was
changed to substantially 65°C. The aqueous solution had a solid content of 30% by
mass, and as a result of determination by the above described methods of
determination, it was found that the aqueous solution had a phosphorus content of
0.029% and an organic phosphorus content of 0.014%, based on the solid content.
The results of the low-temperature stability test (-5°C) and the
high-temperature stability test for the aqueous solution of sodium
N-lauroyl-L-aspartate obtained here were "excellent" and "good", respectively.
Comparative Example 38
An aqueous solution of sodium N-lauroyl-L-aspartate was obtained by the
same operation as in Example 55 except that lauroyl chloride (about 5.2 mol) having
a phosphorus content of the detection limit (1 ppm) or less was used in Example 55.

The aqueous solution had a solid content of 30% by mass, and as a result of
determination by the above described methods of determination, it was found that the
aqueous solution had a phosphorus content of the detection limit or less based on the
solid content. The results of the low-temperature stability test (-5°C) and the
high-temperature stability test for the aqueous solution of sodium
N-lauroyl-L-aspartate obtained were "good" and "bad", respectively.
Comparative Example 39
An aqueous solution of sodium N-lauroyl-L-aspartate was obtained by the
same operation as in Example 55 except that lauroyl chloride having a different
phosphorus content (about 5.2 mol, phosphorus content of 5.0% by mass, and
organic phosphorus content of 1.04% by mass) was used in Example 55. The
aqueous solution had a solid content of 30% by mass, and as a result of
determination by the above described methods of determination, it was found that the
aqueous solution had a phosphorus content of 0.32% and an organic phosphorus
content of 0.12%, based on the solid content.
The results of the low-temperature stability test (-5°C) and the
high-temperature stability test for the aqueous solution of sodium
N-lauroyl-L-aspartate obtained here were "bad" and "good", respectively.
Industrial Applicability
The cleansing composition of the present invention is excellent in feelings
upon use in that it has creamy foaming, is excellent in foaming, exhibits excellent
cleansing power, and provides a refreshed feeling and no stretched feeling of skin
after cleansing. All of these properties are stably maintained during a long-term
storage at 25°c under an acidic condition. When the pH of the cleansing
composition is made weakly acidic again after the long-term storage, it has the same

level of high foaming power as that before it is subjected to the long-term storage.
The aqueous solution of the cleansing composition does not form precipitates even at
low temperatures. The cleansing composition cither in the form of an aqueous
solution or a solid thereof does not exhibit yellowing over a long period of time when
exposed to elevated temperatures. Since the cleansing composition of the present
invention has various excellent characteristics as described above, it can be suitably
utilized in the fields of cosmetics and cleansing applications.

WE CLAIM:
1. A cleansing composition, comprising:
(A) N-acyl-aspartlc acid or a salt thereof represented by formula
(1):

wherein R is an alkyl group having 7 to 23 carbon atoms, and M1
and M2 are each, independently, a hydrogen atom, an alkali metal, an
alkaline earth metal, ammonium, alkylammonium, alkanolammonium
or a protonated basic amino acid;
(B) N-acyl-dlaspartlc acid or a salt thereof, represented by formula
(2):


wherein R is the same alkyl group specified in formula (1), and M3,
M4 and M5 are each, Independently, a hydrogen atom, an alkali
metal, an alkaline earth metal, ammonium,alkylammonium, alkanol-
ammonlum or a protonated basic amino acid; or represented by
formula (3):

wherein R is the same as in formula (2), and M6, M7 and M8 are each,
Independently, a hydrogen atom, an alkali metal, an alkaline earth
metal, ammonium, aikylammonium, alkanolammonium or a
protonated basic amino acid; and (c) a higher fatty acid or a salt
thereof represented by formula (4):


wherein R is the same as in formula (2), and M9 is a hydrogen atom,
an alkali metal, an alkaline earth metal, ammonium, alkylammonium,
alkanolammonium or a protonated basic amino acid, wherein the
weight ratio of N-acyl-diaspartic acid or a salt thereof represented by
formula (2) to N-acyl-diaspartic acid or a salt thereof represented by
formula (3) is 1:3 to 3:1.
2. The cleansing composition as claimed In claim 1, wherein the
amount of component (B) is 0.1 to 15% by mass based on the
total amount of components (A) and (B), and the amount of
component (C) is 0.1 to 15% by mass based on the total amount
of components (A) and (C).
3. The cleansing composition as claimed in claim 2, wherein the
amount of component (B) is 0.1 to 8% by mass based on the total
amount of components (A) and (B), and the amount of component
(C) is 0.1 to 10% by mass based on the total amount of
components (A) and (C).
4. The cleansing composition as claimed In any of claims 1 to 3,
wherein the composition has a pH of from 5.0 to 7.0.

5. The cleansing composition as claimed in any of the claims 1
to 4, wherein R in component (A) has from 9 to 17 carbon atoms.
6. The cleansing composition as claimed in any of claims 1 to 5,
wherein M1 to M9 in formulas (1) to (4) are one or more selected
from a hydrogen atom, sodium, lithium, potassium, ammonium
and triethanolammonium.
7. The cleansing composition as claimed In claim 6, wherein M1
to M9 in formulas (1) to (4) are only one selected from sodium,
lithium ,potassium, ammonium and triethanolammonium, other
than a hydrogen atom.
8. The cleansing composition as claimed in claim 7, wherein M1
to M9 In formulas (1) to (4) are selected only from a hydrogen
atom and sodium.
9. A cleansing composition as claimed In claims 1 to 8,
comprising component (A) represented by formula (1), wherein
after the composition Is stored at 50°C for 30 days, the reduction
In foaming power thereof is 20% or less.

10. The cleansing composition as claimed in claim 9, wherein
after the composition is stored at 50°C for 30 days, the Increase in
the content of a free fatty acid based on component (A) is 15% by
mass or less.
11. The cleansing composition as claimed in any of claims 9 to
10, wherein the composition has a pH of from 4.5 to 6.0.
12. The cleansing composition as claimed in any of claims 9 to
11, further comprising component (D) which comprises one or
more selected from inorganic salts and organic acid alkali metal
salts, wherein the amount of component (D) is from 0.01 to 50%
by mass based on the amount of component (A).
13. A method for producing a cleansing composition as claimed
in claim 1 in which N-acyl-aspartlc acid or a salt thereof is used as
component (A), wherein the N-acyl-aspartic acid or a salt thereof
is prepared by the steps comprising:
adjusting the N-acyl-aspartic acid or a salt thereof to a pH
of 6.0 or higher; and then
adjusting the resulting mixture to a final pH of from 4.5 to
6.0,

wherein the difference between the highest pH and the final pH is
0.5 or more.
14. A cleansing composition as claimed In claim 1 wherein the
composition comprises component (A) represented by formula (I)
which is neutralized to a pH in the range of from 6.6 to 10; after
the composition is stored at 50°C for 30 days, the reduction in
foaming power thereof in a weakly acidic region is 10% or less;
and the reduction in the measured value of visible-light
transmittance at a wavelength of 430 nm Is 10% or less.
15. The cleansing composition as claimed in claim 14,
comprising component (A) represented by formula (1), component
(B) represented by formula(2) or (3), and component (C)
represented by formula (4).
16. The cleansing composition as claimed in claim 15, wherein
component (B) comprises N-acyl-diaspartic acid or a salt thereof
represented by formula (2) and N-acyl-diaspartic acid or a salt
thereof represented by formula (3).

17. The cleansing composition as claimed in claim 16, wherein
the weight of N-acyl-diaspartic acid or a salt thereof represented
by the formula (2) to N-acyl-diaspartic acid or a salt thereof
represented by formula (3) is 1:3 to 3:1.
18. The cleansing composition as claimed in any of claims 15 to
17, wherein the amount of component (B) is 0.1 to 15% by mass
based on the total amount of components (A) and (B), and the
amount of component (C) is 0.1 to 15% by mass based on the
total amount of components (A) and (C).
19. The cleansing composition as claimed in any of claims 14 to
18, wherein the content of the component (A) in which the alkyl
group in formula (1) has 11 carbon atoms is 50% by mol or more
of the total component (A).
20. The cleansing composition as claimed in any of claims 14 to
19, wherein M1 and M2 in formula (1) are an alkali metal salt in
addition to a hydrogen atom.
21. The cleansing composition as claimed in claim 20,wherein
M1 and M2 in formula (1) are each sodium in addition to a

hydrogen atom.
22. The cleansing composition as claimed in any of claims 1 to
21 comprising from 0.005 to 0.3 part by mass of phosphorus.
23. The cleansing composition as claimed in any of claims 1 to
21, comprising from 0.005 to 0.08 part by mass of organic
phosphorus.

There is provided a cleansing composition which has creamy foaming and
excellent cleansing power, provides no stretched feeling of skin after rinsing and a
refreshed feeling of skin, is excellent in storage stability and exhibits no reduction in
physical properties, formation of precipitates and yellowing during a long-term
storage period by combining N-acyl-aspartic acid or a salt thereof and
N-acyl-diaspartic acid or a salt thereof, which have the same molecular structure of
the N-acyl group, with a higher fatty acid or a salt thereof which has the same alkyl
group as that of the above described N-acyl residue.

Documents:

676-KOLNP-2006-FORM-27.pdf

676-kolnp-2006-granted-abstract.pdf

676-kolnp-2006-granted-claims.pdf

676-kolnp-2006-granted-correspondence.pdf

676-kolnp-2006-granted-description (complete).pdf

676-kolnp-2006-granted-examination report.pdf

676-kolnp-2006-granted-form 1.pdf

676-kolnp-2006-granted-form 18.pdf

676-kolnp-2006-granted-form 2.pdf

676-kolnp-2006-granted-form 3.pdf

676-kolnp-2006-granted-form 5.pdf

676-kolnp-2006-granted-gpa.pdf

676-kolnp-2006-granted-reply to examination report.pdf

676-kolnp-2006-granted-specification.pdf

676-kolnp-2006-granted-translated copy of priority document.pdf


Patent Number 227327
Indian Patent Application Number 676/KOLNP/2006
PG Journal Number 02/2009
Publication Date 09-Jan-2009
Grant Date 06-Jan-2009
Date of Filing 22-Mar-2006
Name of Patentee ASAHI KASEI CHEMICALS CORPORATION
Applicant Address 1-2, YURAKU-CHO 1-CHOME, CHIYODA-KU, TOKYO
Inventors:
# Inventor's Name Inventor's Address
1 KIDA YUSUKE 803-6-106, OGURA, SAIWAI-KU, KAWASAKI-SHI KANAGAWA
2 TAMURA YOSHINAGA 2-2-1-1111, HAMACHO, FUNABASHI-SHI, CHIBA
PCT International Classification Number A61K 8/44
PCT International Application Number PCT/JP2004/013887
PCT International Filing date 2004-09-24
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2003-344358 2003-10-02 Japan