U.S. patent application number 14/096397 was filed with the patent office on 2014-04-10 for emulsified composition.
This patent application is currently assigned to KAO CORPORATION. The applicant listed for this patent is KAO CORPORATION. Invention is credited to Masanori Orita, Chihiro Ueyama, Tomokazu Yoshida.
Application Number | 20140100276 14/096397 |
Document ID | / |
Family ID | 43429020 |
Filed Date | 2014-04-10 |
United States Patent
Application |
20140100276 |
Kind Code |
A1 |
Orita; Masanori ; et
al. |
April 10, 2014 |
EMULSIFIED COMPOSITION
Abstract
The emulsion composition of the present invention contains (A)
0.001 to 10 wt. % of an organic compound having two or more
hydroxyl groups, an inorganic value of 220 to 450, and an organic
value of 300 to 1,000; (B) 0.001 to 10 wt. % of an organic compound
having one hydroxyl group, an inorganic value of 100 to 200, and an
organic value of 280 to 700; (C) 0.001 to 10 wt. % of a compound
represented by formula (2): wherein R.sup.1 is a C4 to C30
hydrocarbon group; Z is a methylene group, a methine group, or an
oxygen atom; X.sup.1, X.sup.2, X.sup.3 is a hydrogen atom, a
hydroxyl group, or an acetoxy group; X.sup.4 is a hydrogen atom, an
acetyl group, or a glyceryl group; each of R.sup.2 and R.sup.3 a
hydrogen atom, a hydroxyl group, a hydroxymethyl group, or an
acetoxymethyl group; R.sup.4 is a C5 to C60 hydrocarbon group; and
R.sup.5 is a hydrogen atom or a hydrocarbon group containing 1 to
30 carbon atoms in total; (D) 0.00012 to 10 wt. % of at least one
compound selected from the group consisting of a nonionic
surfactant having a polyoxyethylene group and an HLB of 10 or
higher, an ionic surfactant, and a sphingosine salt; (E) 0.003 to
15 wt. % of at least one compound selected from the group
consisting of a sugar alcohol selected from the group consisting of
erythritol, threitol, xylitol, and mannitol, a disaccharide, and a
trisaccharide; and (F) water. ##STR00001##
Inventors: |
Orita; Masanori; (Sumida-ku,
JP) ; Yoshida; Tomokazu; (Sumida-ku, JP) ;
Ueyama; Chihiro; (Sumida-ku, JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
KAO CORPORATION |
Chuo-ku |
|
JP |
|
|
Assignee: |
KAO CORPORATION
Chuo-ku
JP
|
Family ID: |
43429020 |
Appl. No.: |
14/096397 |
Filed: |
December 4, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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13382298 |
Jan 5, 2012 |
8647649 |
|
|
PCT/JP2010/004414 |
Jul 6, 2010 |
|
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14096397 |
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Current U.S.
Class: |
514/552 |
Current CPC
Class: |
A61K 8/86 20130101; A61K
8/60 20130101; A61K 8/68 20130101; A61K 8/37 20130101; A61K 8/06
20130101; A61K 8/345 20130101; A61Q 19/00 20130101; A61K 8/375
20130101; A61K 8/342 20130101; A61K 8/41 20130101 |
Class at
Publication: |
514/552 |
International
Class: |
A61K 8/68 20060101
A61K008/68; A61K 8/34 20060101 A61K008/34; A61Q 19/00 20060101
A61Q019/00; A61K 8/37 20060101 A61K008/37 |
Foreign Application Data
Date |
Code |
Application Number |
Jul 6, 2009 |
JP |
2009-159737 |
Jul 6, 2009 |
JP |
2009-159738 |
Claims
1-11. (canceled)
12: An emulsion composition comprising the following ingredients
(A), (B), (C), (D), (E), and (F): (A) from 0.05 to 7 wt. % of at
least one organic compound selected form the group consisting of a
glycerin monofatty acid ester, a glycerin monoalkyl ether, a
sorbitan monofatty acid ester, and a sorbitan difatty acid ester;
(B) from 0.05 to 7 wt. % of at least one organic compound selected
from the group consisting of a C14 to C22 higher alcohol and a
sterol; (C) from 0.05 to 7 wt. % of at least one compound of the
formula (2): ##STR00016## wherein R.sup.1 represents a C4 to C30
linear, branched, or cyclic, saturated or unsaturated hydrocarbon
group which may be substituted by a hydroxyl group, a carbonyl
group, or an amino group; Z represents a methylene group, a methine
group, or an oxygen atom; each of X.sup.1, X.sup.2, and X.sup.3
represents a hydrogen atom, a hydroxyl group, or an acetoxy group;
X.sup.4 represents a hydrogen atom, an acetyl group, or a glyceryl
group, or forms an oxo group together with the adjacent oxygen
atom, wherein when Z is a methine group, one of X.sup.1 and X.sup.2
is a hydrogen atom, and the other is absent, and when X.sup.4 forms
an oxo group, X.sup.3 is absent; each of R.sup.2 and R.sup.3
represents a hydrogen atom, a hydroxyl group, a hydroxymethyl
group, or an acetoxymethyl group; R.sup.4 represents a C5 to C60
linear, branched, or cyclic, saturated or unsaturated hydrocarbon
group which may be substituted by a hydroxyl group, a carbonyl
group, or an amino group and which may have an ether bond, an ester
bond, or an amide bond in a backbone thereof; and R.sup.5
represents a hydrogen atom, or a linear or branched, saturated or
unsaturated hydrocarbon group optionally having a substituent
selected from the group consisting of a hydroxyl group, a
hydroxyalkoxy group, an alkoxy group, and an acetoxy group and
containing 1 to 30 carbon atoms in total; and the broken line
represents an optional unsaturated bond; (D) from 0.01 to 7 wt. %
of at least one compound selected from the group consisting of a
C12 to C24 fatty acid salt, a fatty acid amidesulfonate salt, a
polyoxyethylene alkyl ether phosphate salt, a long-chain
N-acylglutamate salt, and a sphingosine salt; (E) at least one
compound selected from the group consisting of a sugar alcohol
selected from the group consisting of erythritol, threitol,
xylitol, and mannitol, and a disaccharide or a trisaccharide
selected from the group consisting of trehalose, raffinose,
lactose, galactosylfructose, sucralose, and melibiose, wherein an
amount of the sugar alcohol is form 0.01 to 5% by mass; and an
amount of a disaccharide or a trisaccharide is from 0.1 to 15% by
mass; and (F) water, wherein a ratio ((A)+(B))/((A)+(B)+(C)) is
0.15 or more, and wherein a weight ratio (E)/((A)+(B)+(C)) is from
0.01 to 3, when the ingredient (E) is the sugar alcohol, and from
0.2 to 5, when the ingredient (E) is the disaccharide or
trisaccharide.
13: An emulsion composition comprising the following ingredients
(A), (B), (C), (D), (E), and (F): (A) from 0.05 to 7 wt. % of at
least one organic compound selected form the group consisting of a
glycerin monofatty acid ester, a glycerin monoalkyl ether, a
sorbitan monofatty acid ester, and a sorbitan difatty acid ester;
(B) from 0.05 to 7 wt. % of at least one organic compound selected
from the group consisting of a C14 to C22 higher alcohol and a
sterol; (C) from 0.05 to 7 wt. % of at least one compound of the
following formula (2): ##STR00017## wherein R.sup.1 represents a C4
to C30 linear, branched, or cyclic, saturated or unsaturated
hydrocarbon group which may be substituted by a hydroxyl group, a
carbonyl group, or an amino group; Z represents a methylene group,
a methine group, or an oxygen atom; each of X.sup.1, X.sup.2, and
X.sup.3 represents a hydrogen atom, a hydroxyl group, or an acetoxy
group; X.sup.4 represents a hydrogen atom, an acetyl group, or a
glyceryl group, or forms an oxo group together with the adjacent
oxygen atom, wherein when Z is a methine group, one of X.sup.1 and
X.sup.2 is a hydrogen atom, and the other is absent, and when
X.sup.4 forms an oxo group, X.sup.3 is absent; each of R.sup.2 and
R.sup.3 represents a hydrogen atom, a hydroxyl group, a
hydroxymethyl group, or an acetoxymethyl group; R.sup.4 represents
a C5 to C60 linear, branched, or cyclic, saturated or unsaturated
hydrocarbon group which may be substituted by a hydroxyl group, a
carbonyl group, or an amino group and which may have an ether bond,
an ester bond, or an amide bond in a backbone thereof; and R.sup.5
represents a hydrogen atom, or a linear or branched, saturated or
unsaturated hydrocarbon group optionally having a substituent
selected from the group consisting of a hydroxyl group, a
hydroxyalkoxy group, an alkoxy group, and an acetoxy group and
containing 1 to 30 carbon atoms in total; and the broken line
represents an optional unsaturated bond; (D) from 0.01 to 7 wt. %
of at least one compound selected from the group consisting of a
nonionic surfactant having a polyoxyethylene group and an HLB of 10
or higher, an ionic surfactant, and a sphingosine salt, wherein the
nonionic surfactant is selected from the group consisting of a
polyoxyethylene hydrogenated castor oil, a polyoxyethylene sorbitan
fatty acid ester, an alkylpolyoxyethylene glycerol, and a
polyoxyethylene alkyl ether; (E) at least one compound selected
from the group consisting of a sugar alcohol selected from the
group consisting of erythritol, threitol, xylitol, and mannitol,
and a disaccharide or a trisaccharide selected from the group
consisting of trehalose, raffinose, lactose, galactosylfructose,
sucralose, and melibiose, wherein an amount of the sugar alcohol is
form 0.01 to 5% by mass; and an amount of a disaccharide or a
trisaccharide is from 0.1 to 15% by mass; and (F) water, wherein,
when the ingredient (E) is the sugar alcohol, a weight ratio of the
ingredients (A), (B), (C) and (E), (E)/((A)+(B)+(C)), is from 0.125
to 3, and when the ingredient (E) is the disaccharide or
trisaccharide, a weight ratio (E)/((A)+(B)+(C)) is from 0.2 to
5.
14. The emulsion composition according to claim 13, wherein the
ingredient (D) is a nonionic surfactant selected from the group
consisting of a polyoxyethylene hydrogenated castor oil and a
polyoxyethylene sorbitan fatty acid ester.
15. The emulsion composition according to claim 12, wherein a fatty
acid and/or alkyl moiety of the ingredient (A) is linear, and
wherein the ingredient (B) is at least one selected from the group
consisting of a linear C14 to C22 higher alcohol and a sterol.
16: The emulsion composition according to claim 13, wherein the
ingredient (A) is a compound represented by the following formula
(1): Z.sup.1 Y.sup.1--R).sub.n (1) wherein Z.sup.1 represents a
structure which is a glycerin residue, a sorbitan residue, a
sorbitol residue, or a sucrose residue having two or more hydroxyl
groups; Y.sup.1 represents an ester bond or an ether bond; R
represents a C14 to C22 hydrocarbon group; and n is a number of 1
or 2, and wherein a fatty acid and/or alkyl moiety of the
ingredient (A) is linear.
17. The emulsion composition according to claim 12, wherein the
weight ratio of the ingredients (A), (B), (C) and (E),
(E)/((A)+(B)+(C)), is from 0.125 to 3, when the ingredient (E) is
the sugar alcohol, and from 0.6 to 5, when the ingredient (E) is
the disaccharide or trisaccharide.
18. The emulsion composition according to claim 12, which forms an
.alpha.-gel structure.
19. The emulsion composition according to claim 12, wherein the
weight ratio of the ingredients (A), (B), and (C),
((A)+(B))/((A)+(B)+(C)), is from 0.15 to 0.95.
20. The emulsion composition according to claim 12, wherein the
weight ratio of the ingredients (A) and (B), (A)/((A)+(B)), is from
0.25 to 0.75.
21. A method for producing an emulsion composition as recited in
claim 12, the method comprising mixing a mixture containing
ingredients (A) to (E) with an aqueous phase containing ingredient
(F), to thereby forming the emulsion.
22. A method for producing an emulsion composition as recited in
claim 12, the method comprising mixing a mixture containing
ingredients (A) to (D) with an aqueous phase containing ingredients
(E) and (F), thereby forming the emulsion.
23. The emulsion composition according to claim 13, which forms an
.alpha.-gel structure.
24. The emulsion composition according to claim 13, wherein a
weight ratio of the ingredients (A), (B), and (C),
((A)+(B))/((A)+(B)+(C)), is from 0.15 to 0.95.
25. The emulsion composition according to claim 13, wherein a
weight ratio of the ingredients (A) and (B), (A)/((A)+(B)), is from
0.25 to 0.75.
26. A method for producing an emulsion composition as recited in
claim 13, the method comprising mixing a mixture containing
ingredients (A) to (E) with an aqueous phase containing ingredient
(F), thereby forming the emulsion.
27. A method for producing an emulsion composition as recited in
claim 13, the method comprising mixing a mixture containing
ingredients (A) to (D) with an aqueous phase containing ingredients
(E) and (F), thereby forming the emulsion.
28. The emulsion composition according to claim 13, wherein a
weight ratio of the ingredients (A), (B), (C),
((A)+(B))/((A)+(B)+(C)), is 0.15 or more.
29. The emulsion composition according to claim 12, wherein a
weight ratio of the ingredients (A), (B), (C), and (D),
(D)/((A)+(B)+(C)), is form 0.04 to 1.
30. The emulsion composition according to claim 13, wherein a
weight ratio of the ingredients (A), (B), (C), and (D),
(D)/((A)+(B)+(C)), is form 0.04 to 1.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a Continuation of U.S. application Ser.
No. 13/382,298, filed Jan. 5, 2012, which is the National Stage of
International Application No. PCT/JP2010/004414, filed Jul. 6,
2010, which claims priority to Japanese Patent Application No.
2009-159737, filed Jul. 6, 2009 and Japanese Patent Application
2009-159738, filed Jul. 6, 2009; of which all of the disclosures
are incorporated herein by reference in their entireties.
FIELD OF THE INVENTION
[0002] The present invention relates to an emulsion composition
which allows water to remain in the skin for a long period of
time.
BACKGROUND OF THE INVENTION
[0003] .alpha.-Gel has a hydrate-type crystal structure, which is a
lamellar structure. The intercellular lipid present in the horny
layer (i.e., the outermost skin layer) generally has the
.alpha.-gel structure, and prevents entry of outside substances
into the skin as well as transepidermal water loss. Also, the
intercellular lipid itself retains water, whereby the softness and
smooth appearance of the skin can be maintained. In the skin, the
horny layer retains water as bound water in an amount of about 33%.
Studies have revealed that the intercellular lipid retains about
13% of the bound water (here, bound water is defined as water
restrained by molecules forming the horny layer) (Non-Patent
Document 1).
[0004] For example, Patent Document 1 discloses that an emulsion
composition containing a ceramide and other ingredients forms an
.alpha.-gel structure, to thereby enhance a moisturizing effect.
When the skin surface is covered with such an .alpha.-gel, as
covered with the intercellular lipid, the skin is expected to
retain a sufficient amount of water under dry conditions, to
thereby attain long-lasting moistness.
[0005] Meanwhile, low-molecular-weight compounds such as glycerin
and amino acid as well as high-molecular-weight compounds such as
hyaluronic acid are thought to have a high moisture retention
property. However, since the water content of an aqueous solution
of a single ingredient is generally limited to the bound water
level, a preparation containing such an ingredient attains
unsatisfactory water retention. In addition, although the
aforementioned .alpha.-gel is expected to exhibit satisfactory
water retention, solid fat that constitutes .alpha.-gel provides
users a heavy feeling upon use. Thus, when the amount of
.alpha.-gel is simply increased to enhance water retention, a good
feeling upon use is impaired (e.g., sticky feeling upon use).
PRIOR ART DOCUMENTS
Non-Patent Documents
[0006] Non-Patent Document 1: Genji IMOKAWA, Oil Chemistry, 44, 10,
p. 51-66(1995)
Patent Documents
[0006] [0007] Patent Document 1: JP-A-2007-22997
SUMMARY OF THE INVENTION
Problems to be Solved by the Invention
[0008] The present invention is directed to an emulsion composition
which can retain bound water and free water (i.e., water retained
in the interlamellar layers but not restrained by a lamellar
structure ingredient) in the interlamellar layers of an .alpha.-gel
lamellar structure, allowing water to be retained in the skin for a
long period of time, to thereby improve skin conditions.
Means for Solving the Problems
[0009] The present inventors have found that, through a combination
of an .alpha.-gel designed to have enhanced water retention with a
specific sugar alcohol, disaccharide, or trisaccharide, there can
be produced an emulsion composition which can enhance water
retention of .alpha.-gel, allowing water to be retained in the skin
for a long period of time, to thereby improve skin conditions.
[0010] The present invention provides an emulsion composition
containing the following ingredients (A), (B), (C), (D), (E), and
(F):
[0011] (A) 0.001 to 10 wt. % of an organic compound having two or
more hydroxyl groups, an inorganic value of 220 to 450, and an
organic value of 300 to 1,000;
[0012] (B) 0.001 to 10 wt. % of an organic compound having one
hydroxyl group, an inorganic value of 100 to 200, and an organic
value of 280 to 700;
[0013] (C) 0.001 to 10 wt. % of a compound represented by formula
(2):
##STR00002##
(wherein R.sup.1 represents a C4 to C30 linear, branched, or
cyclic, saturated or unsaturated hydrocarbon group which may be
substituted by a hydroxyl group, a carbonyl group, or an amino
group; Z represents a methylene group, a methine group, or an
oxygen atom; each of X.sup.1, X.sup.2, and X.sup.3 represents a
hydrogen atom, a hydroxyl group, or an acetoxy group; X.sup.4
represents a hydrogen atom, an acetyl group, or a glyceryl group,
or forms an oxo group together with the adjacent oxygen atom
(wherein when Z is a methine group, one of X.sup.1 and X.sup.2 is a
hydrogen atom, and the other is absent, and when X.sup.4 forms an
oxo group, X.sup.3 is absent); each of R.sup.2 and R.sup.3
represents a hydrogen atom, a hydroxyl group, a hydroxymethyl
group, or an acetoxymethyl group; R.sup.4 represents a C5 to C60
linear, branched, or cyclic, saturated or unsaturated hydrocarbon
group which may be substituted by a hydroxyl group, a carbonyl
group, or an amino group and which may have an ether bond, an ester
bond, or an amide bond in a backbone thereof; R.sup.5 represents a
hydrogen atom, or a linear or branched, saturated or unsaturated
hydrocarbon group optionally having a substituent selected from the
group consisting of a hydroxyl group, a hydroxyalkoxy group, an
alkoxy group, and an acetoxy group and containing 1 to 30 carbon
atoms in total; and the broken line represents an optional
unsaturated bond);
[0014] (D) 0.00012 to 10 wt. % of at least one compound selected
from the group consisting of a nonionic surfactant having a
polyoxyethylene group and an HLB of 10 or higher, an ionic
surfactant, and a sphingosine salt;
[0015] (E) 0.003 to 15 wt. % of at least one compound selected from
the group consisting of a sugar alcohol selected from the group
consisting of erythritol, threitol, xylitol, and mannitol, a
disaccharide, and a trisaccharide; and
[0016] (F) water.
Effects of the Invention
[0017] The emulsion composition of the present invention contains,
as active ingredients, ingredients (A), (B), and (C) and forms a
uniform a structure having high steric regularity. Thus, the
emulsion composition has enhanced water retention and allows water
to remain in the skin for a long period of time, whereby the skin
conditions can be improved. When the composition is applied to the
skin, excellent skin permeability and long-lasting moistness can be
obtained. In addition, the composition enables formation on the
skin surface of a soft coating layer having a lamellar-like
structure, whereby water can be retained in the interlayer space,
to thereby enhance a skin protection effect.
BRIEF DESCRIPTION OF THE DRAWINGS
[0018] FIG. 1 A graph employed for measuring remaining water
content in the Examples and Comparative Examples.
MODES FOR CARRYING OUT THE INVENTION
Ingredient (A)
[0019] Ingredient (A) employed in the present invention is an
organic compound having two or more hydroxyl groups, an inorganic
value of 220 to 450, and an organic value of 300 to 1,000.
Preferable examples of ingredient (A) include an organic compound
having an inorganic value of 220 to 340 and an organic value of 380
to 840, more preferably an organic compound having an inorganic
value of 250 to 340 and organic value of 380 to 700, from the
viewpoint of formability of a lamellar structure with the
below-mentioned other ingredients.
[0020] In the present invention, the terms "inorganic value" and
"organic value" refer to those obtained from an organic conceptual
diagram (see "Prediction of Organic Compounds by a Conceptual
Diagram" described by Atsushi FUJITA, Kagaku-no-Ryouiki, Vol. 11,
No. 10 (1957) 719-725).
[0021] Examples of ingredient (A) include compounds represented by
formula (1):
Z.sup.1 Y.sup.1--R).sub.n (1)
(wherein Z.sup.1 represents a structure which is a glycerin
residue, a sorbitan residue, a sorbitol residue, or a sucrose
residue having two or more hydroxyl groups; Y.sup.1 represents an
ester bond or an ether bond; R represents a C14 to C22 hydrocarbon
group; and n is a number of 1 or 2).
[0022] In formula (1), the C14 to C22 hydrocarbon group R is
preferably a linear hydrocarbon group, such as a linear alkyl group
(e.g., myristyl, palmityl, stearyl, or behenyl), a palmitoyl group,
or an oleyl group.
[0023] Examples of the compound represented by formula (1) include
glycerin monofatty acid ester, sorbitan monofatty acid ester,
sorbtian difatty acid ester, sorbitol monofatty acid ester,
sorbitol difatty acid ester, sucrose monofatty acid ester, and
glycerin monoalkyl ether.
[0024] Ingredient (A) is preferably glycerin monofatty acid ester,
glycerin monoalkyl ether, sorbitan monofatty acid ester, or
sorbtian difatty acid ester. Among them, glyceryl monopalmitate
(inorganic value 260, organic value 380), glyceryl monostearate
(inorganic value 260, organic value 420), glyceryl monobehenate
(inorganic value 260, organic value 500), monocetyl glyceryl ether
(inorganic value 220, organic value 380), monostearyl glyceryl
ether (inorganic value 220, organic value 420), sorbitan
monostearate (inorganic value 445, organic value 480), and sorbitan
distearate (inorganic value 340, organic value 840) are preferred.
Of these, glyceryl monobehenate and monocetyl glyceryl ether are
more preferred, for enhancing lamellar film formability and water
retention, as mentioned hereinbelow.
[0025] Ingredient (A) employed in the present invention may be one
or more species. The composition of the invention has an ingredient
(A) content of 0.001 to 10 wt. %, preferably 0.05 to 7 wt. %, more
preferably 0.1 to 3 wt. %, in the total composition, since water
retention is enhanced.
Ingredient (B)
[0026] Ingredient (B) employed in the present invention is an
organic compound having one hydroxyl group, an inorganic value of
100 to 200, and an organic value of 280 to 700. For ingredient (B),
more preferred is an organic compound having an inorganic value of
100 to 182 and an organic value of 300 to 520, from the viewpoint
of formability of a lamellar structure with ingredient (A) and the
below-mentioned ingredients.
[0027] Specific examples of the organic compound include one or
more compounds selected from the group consisting of a C14 to C22
higher alcohol and a sterol.
[0028] The higher alcohol is a C14 to C22 alcohol, preferably C16
to C18 alcohol. Examples of the higher alcohol include myristyl
alcohol (inorganic value 100, organic value 280), cetanol
(inorganic value 100, organic value 320), stearyl alcohol
(inorganic value 100, organic value 360), behenyl alcohol
(inorganic value 100, organic value 440), and oleyl alcohol
(inorganic value 102, organic value 360).
[0029] Among them, an alcohol having a linear alkyl group is
preferred, with cetanol and stearyl alcohol being more
preferred.
[0030] Examples of the sterol include cholesterol (inorganic value
182, organic value 520) and phytosterol. The term "phytosterol"
collectively refers to plant-derived sterols such as
.beta.-sitosterol, campesterol, stigmasterol, and brassicasterol,
and no particular limitation is imposed on the ingredient
composition thereof.
[0031] Ingredient (B) employed in the composition may include one
or more species. The composition contains ingredient (B) in an
amount of 0.001 to 10 wt. % with respect to the total composition,
preferably 0.05 to 7 wt. %, more preferably 0.1 to 3 wt. %, for
attaining high water-occluding property.
Ingredient (C)
[0032] Ingredient (C) employed in the present invention is a
compound represented by formula (2).
[0033] In formula (2), R.sup.1 represents a hydrogen atom or a C4
to C30 linear, branched, or cyclic, saturated or unsaturated
hydrocarbon group which may be substituted by a hydroxyl group, a
carbonyl group, or an amino group, and R.sup.1 represents
preferably a C7 to C22 linear, branched, or cyclic, saturated or
unsaturated hydrocarbon group which may be substituted by a
hydroxyl group.
[0034] Z represents a methylene group, a methine group, or an
oxygen atom.
[0035] Each of X.sup.1, X.sup.2, and X.sup.3 represents a hydrogen
atom, a hydroxyl group, or an acetoxy group. In a preferred
embodiment, all of X.sup.1, X.sup.2, and X.sup.3 are not a hydroxyl
group or one of X.sup.1, X.sup.2, and X.sup.3 is a hydroxyl group,
and each of the remaining groups is a hydrogen atom. When Z is a
methine group, one of X.sup.1 and X.sup.2 is a hydrogen atom, and
the other is absent. X.sup.4 is preferably a hydrogen atom or a
glyceryl group.
[0036] Each of R.sup.2 and R.sup.3 represents a hydrogen atom, a
hydroxyl group, a hydroxymethyl group, or an acetoxymethyl group.
R.sup.2 is preferably a hydrogen atom or a hydroxymethyl group, and
R.sup.3 is preferably a hydrogen atom.
[0037] R.sup.4 represents a C5 to C60 linear, branched, or cyclic,
saturated or unsaturated hydrocarbon group which may be substituted
by a hydroxyl group, a carboxyl group, or an amino group and which
may have an ether bond, an ester bond, or an amide bond in a
backbone thereof. R.sup.4 is preferably, for example, a C5 to C35
linear, branched, or cyclic, saturated or unsaturated hydrocarbon
group optionally substituted by a hydroxyl group or an amino group,
or a group formed by bonding a C8 to C22 linear, branched, or
cyclic, saturated or unsaturated fatty acid optionally having a
hydroxyl group to the .omega.-position of the above hydrocarbon
group via an ester bond or an amide bond. The fatty acid bonded to
the hydrocarbon group is preferably isostearic acid,
12-hydroxystearic acid, or linoleic acid.
[0038] R.sup.5 represents a hydrogen atom, or a linear or branched,
saturated or unsaturated hydrocarbon group optionally having a
substituent selected from the group consisting of a hydroxyl group,
a hydroxyalkoxy group, an alkoxy group, and an acetoxy group and
containing 1 to 30 carbon atoms in total. When R.sup.1 is a
hydrogen atom and Z is an oxygen atom, R.sup.5 is a hydrocarbon
group containing 10 to 30 carbon atoms in total. When R.sup.1 is a
hydrocarbon group, R.sup.5 is a hydrocarbon group containing 1 to 8
carbon atoms in total. Among them, preferred are a hydrogen atom
and a hydrocarbon group containing 1 to 8 carbon atoms in total
which group may be substituted by 1 to 3 substituents selected from
the group consisting of a hydroxyl group, a hydroxyalkoxy group,
and an alkoxy group. The hydroxyalkoxy group and the alkoxy group
preferably have 1 to 7 carbon atoms.
[0039] The compound represented by formula (2) is preferably a
ceramide represented by the following formula (3) or (4).
[0040] (I) The compound represented by formula (3) may be a
naturally occurring ceramide or a synthetic product having the same
structure.
##STR00003##
(wherein R.sup.11 represents a C7 to C19 linear, branched or
cyclic, saturated or unsaturated hydrocarbon group which may be
substituted by a hydroxyl group; Z.sub.1 represents a methylene
group or a methine group; each of X.sup.5, X.sup.6, and X.sup.7
represents a hydrogen atom, a hydroxyl group, or an acetoxy group;
X.sup.8 represents a hydrogen atom, or forms an oxo group together
with the adjacent oxygen atom (wherein when Z.sub.1 is a methine
group, one of X.sup.5 and X.sup.6 is a hydrogen atom, and the other
is absent, and when X.sup.8 forms an oxo group, X.sup.7 is absent);
R.sup.12 represents a hydroxymethyl group or an acetoxymethyl
group; R.sup.13 represents a hydrogen atom or a C1 to C4 alkyl
group; R.sup.14 represents a C5 to C30 linear, branched or cyclic,
saturated or unsaturated hydrocarbon group which may be substituted
by a hydroxyl group, or such an alkyl group to which a C8 to C22
linear or branched, saturated or unsaturated fatty acid which may
be substituted by a hydroxyl group is bonded at the .omega.-end via
ester bonding; and the broken line represents an optional
unsaturated bond).
[0041] In a preferred compound, R.sup.11 is a C7 to C19 (more
preferably C13 to C15) linear alkyl group; R.sup.14 is a C9 to C27
linear alkyl group which may be substituted by a hydroxyl group, or
a C9 to C27 linear alkyl group to which linoleic acid is bonded via
ester bonding. Preferably, X.sup.8 is a hydrogen atom or forms an
oxo group together with an oxygen atom. R.sup.14 is preferably
tricosyl, 1-hydroxypentadecyl, 1-hydroxytricosyl, heptadecyl,
1-hydroxyundecyl, or nonacosyl to which linoleic acid is bonded at
the .omega.-position via ester bonding.
[0042] Specific examples of the natural-type ceramide include
sphingosine, dihydrosphingosine, phytosphingosine, and amidated
sphingadienine (Ceramide Types 1 to 7) (see, for example,
pig-origin and human-origin ceramides shown in FIG. 2 in J. Lipid
Res., 24: 759 (1983) and FIG. 4 in J. Lipid. Res., 35: 2069
(1994)).
[0043] N-alkyl forms of these ceramides are also included (e.g.,
N-methyl form).
[0044] Regarding these ceramides, either a natural-type optically
active form (D(-) form) or a non-natural-type optically active form
(L(+) form) may be used. Furthermore, a mixture of a natural-type
form and a non-natural-type form may also be used. The relative
configuration of the aforementioned compound may be ones of
natural-type, of non-natural-type, or of mixed type. Further,
preferred are compounds: CERAMIDE 1, CERAMIDE 2, CERAMIDE 3,
CERAMIDE 5, CERAMIDE 611, (INCI, 8th Edition), and those
represented by the following formulas.
##STR00004##
[0045] These ceramides may be either compounds extracted from
natural ceramides or synthesized ones thereof. Commercially
available ones can also be used.
[0046] Examples of such the commercially available natural type
ceramides include Ceramide I, Ceramide III, Ceramide IIIA, Ceramide
IIIB, Ceramide IIIC, and Ceramide VI (COSMOFERM); Ceramide TIC-001
(Takasago International Corporation); CERAMIDE II (Quest
International); DS-Ceramide VI, DS-CLA-Phytoceramide,
C6-Phytoceramide, and DS-ceramide Y3S (DOOSAN); and CERAMIDE 2
(Sederma).
##STR00005## ##STR00006##
[0047] (II): Pseudo-ceramide represented by formula (4):
##STR00007##
(wherein R.sup.15 represents a hydrogen atom or a C10 to C22
linear, branched, or cyclic, saturated or unsaturated hydrocarbon
group which may be substituted by a hydroxyl group; X.sup.9
represents a hydrogen atom, an acetyl group, or a glyceryl group;
R.sup.16 represents a C5 to C22 linear, branched, or cyclic,
saturated or unsaturated hydrocarbon group which may be substituted
by a hydroxyl group or an amino group, or such a hydrocarbon group
to which a C8 to C22 linear or branched, saturated or unsaturated
fatty acid which may be substituted by a hydroxyl group is bonded
at the .omega.-end via ester bonding; and R.sup.17 represents a
hydrogen atom or an alkyl group optionally having a substituent
selected from the group consisting of a hydroxyl group, a
hydroxyalkoxy group, an alkoxy group, and an acetoxy group and
containing 1 to 30 carbon atoms in total).
[0048] R.sup.16 is preferably nonyl, tridecyl, pentadecyl, undecyl
to which linoleic acid is bonded at the .omega.-position thereof
via ester bonding, pentadecyl to which linoleic acid is bonded at
the .omega.-position thereof via ester bonding, pentadecyl to which
12-hydroxystearic acid is bonded at the .omega.-position thereof
via ester bonding, or undecyl to which methyl-branched isostearic
acid is bonded at the .omega.-position thereof via amide
bonding.
[0049] When R.sup.15 is a hydrogen atom, R.sup.17 is an alkyl group
optionally substituted by a hydroxyl group, a hydroxyalkoxy group,
an alkoxy group, or an acetoxy group and containing 10 to 30
(preferably 12 to 20) carbon atoms in total. When R.sup.15 is a C10
to C22 linear, branched, or cyclic, saturated or unsaturated
hydrocarbon group which may be substituted by a hydroxyl group,
R.sup.17 is preferably a hydrogen atom or an alkyl group optionally
substituted by a hydroxyl group, a hydroxyalkoxy group, an alkoxy
group, or an acetoxy group and containing 1 to 8 carbon atoms in
total. The hydroxyalkoxy or alkoxy group in R.sup.17 preferably
contains 1 to 7 carbon atoms.
##STR00008##
[0050] Preferred pseudo-ceramides represented by formula (4) are
the case where R.sup.15 is hexadecyl, X.sup.9 is a hydrogen atom,
R.sup.16 is pentadecyl, and R.sup.17 is hydroxyethyl; the case
where R.sup.15 is hexadecyl, X.sup.9 is a hydrogen atom, R.sup.16
is nonyl, and R.sup.17 is hydroxyethyl; and the case where R.sup.15
is hexadecyl, X.sup.9 is glyceryl, R.sup.16 is tridecyl, and
R.sup.17 is 3-methoxypropyl. More preferred pseudo-ceramide
represented by formula (4) is the case where R.sup.15 is hexadecyl,
X.sup.9 is a hydrogen atom, R.sup.16 is pentadecyl, and R.sup.17 is
hydroxyethyl (i.e.,
N-(hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide).
##STR00009##
[0051] One or more compounds serving as ingredient (C) may be used.
The total content of ingredient (C) is 0.001 to 10 wt. %,
preferably 0.05 to 7 wt. %, more preferably 0.1 to 5 wt. %, in the
total composition, for attaining sufficient skin permeation of
ingredient (C).
[0052] In the present invention, the weight ratio of ingredients
(A), (B), and (C) preferably have the following relationship:
((A)+(B))/((A)+(B)+(C)) (by weight) of 0.15 or more, more
preferably 0.35 to 0.8, from the viewpoint of enhancing storage
stability of .alpha.-gel.
[0053] The weight ratio of ingredients (A) and (B) preferably have
the following relationship: (A)/((A)+(B)) (by weight) of 0.1 or
more, more preferably 0.25 to 0.75, since stable .alpha.-gel
structure is formed, to thereby enhance water retention.
Ingredient (D)
[0054] The ingredient (D) employed in the present invention is at
least one compound selected from the group consisting of a nonionic
surfactant having a polyoxyethylene group and an HLB of 10 or more,
an ionic surfactant, and a sphingosine salt.
[0055] Among the compounds serving as ingredient (D), the nonionic
surfactant is a hydrophilic compound having a polyoxyethylene group
and an HLB of 10 or more, preferably an HLB of 12.5 to 15.5.
Examples of the non-ionic compound include polyoxyethylene
hydrogenated castor oil, polyoxyethylene sorbitan fatty acid ester,
alkylpolyoxyethylene glyceryl, and polyoxyethylene alkyl ether.
[0056] Of these, polyoxyethylene hydrogenated castor oil and
polyoxyethylene sorbitan monostearate are preferred.
[0057] Among the compounds serving as ingredient (D), the ionic
surfactant is an anionic surfactant, a cationic surfactant, or an
ampholytic surfactant.
[0058] Examples of the anionic surfactant include C12 to C24 fatty
acid salts such as sodium laurate, potassium palmitate, and
arginine stearate; alkyl sulfate ester salts such as sodium lauryl
sulfate and potassium lauryl sulfate; alkyl ether sulfate ester
salts such as polyoxyethylene lauryl sulfate triethanolamine salt;
N-acylsarcosine salts such as lauroyl sarcosine sodium salt; fatty
acid amide sulfonate salts such as sodium methyl stearoyl
taurate(N-stearoyl-N-methyltaurine sodium salt) and sodium methyl
myristoyl taurate(N-myristoyl-N-methyltaurine sodium salt); alkyl
phosphate salts such as sodium monostearyl phosphate;
polyoxyethylene alkyl ether phosphate salts such as sodium
polyoxyethylene oleyl ether phosphate and sodium polyoxyethylene
stearyl ether phosphate; long-chain sulfosuccinate salts such as
sodium di-2-ethylhexylsulfosuccinate; and long-chain
N-acylglutamate salts such as monosodium N-lauroylglutamate, sodium
N-stearoyl-L-glutamate, arginine N-stearoyl-L-glutamate, sodium
N-stearoylglutamate, and sodium N-myristoyl-L-glutamate.
[0059] Among them, C12 to C24 fatty acid salts, fatty acid
amidesulfonate salts, polyoxyethylene alkyl ether phosphate salts,
and long-chain N-acylglutamate salts are preferred, with sodium
methyl stearoyl taurate(N-stearoyl-N-methyltaurine sodium salt),
arginine N-stearoyl-L-glutamate, and sodium polyoxyethylene stearyl
ether phosphate being more preferred.
[0060] The cationic surfactant is preferably a quaternary ammonium
salt. Examples include alkyltrimethylammonium salts such as stearyl
trimethylammonium chloride and lauryl trimethylammonium chloride;
dialkyldimethylammonium salts; trialkylmethylammonium salts; and
alkylamine salts.
[0061] Examples of the ampholytic surfactant include
alkyldimethylamine oxide, alkylcarboxybetaine, alkylsulfobetaine,
amideamino acid salts, and alkylamidepropylbetaine. Of these,
alkylamidepropylbetaine is preferred.
[0062] Among the compounds serving as ingredient (D) employed in
the present invention, the sphingosine salt is formed of a
sphingosine and an acidic substance. Examples of the sphingosine
include those represented by formula (5):
##STR00010##
(wherein R.sup.21 represents a C4 to C30 linear, branched, or
cyclic, saturated or unsaturated hydrocarbon group which may be
substituted by a hydroxyl group, a carbonyl group, or an amino
group; Y represents a methylene group, a methine group, or an
oxygen atom; each of X.sup.11, X.sup.12, and X.sup.13 represents a
hydrogen atom, a hydroxyl group, or an acetoxy group; X.sup.14
represents a hydrogen atom, an acetyl group, or a glyceryl group,
or forms an oxo group together with the adjacent oxygen atom
(wherein when Y is a methine group, one of X.sup.11 and X.sup.12 is
a hydrogen atom, and the other is absent, and when X.sup.14 forms
an oxo group, X.sup.13 is absent); each of R.sup.22 and R.sup.23
represents a hydrogen atom, a hydroxyl group, a hydroxymethyl
group, or an acetoxymethyl group; each of the "a" groups of
R.sub.1s represents a hydrogen atom, an amidino group, or a linear
or branched, saturated or unsaturated hydrocarbon group optionally
having a substituent selected from the group consisting of a
hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an
acetoxy group and containing 1 to 8 carbon atoms in total; a is a
number of 2 or 3; and the broken line represents an optional
unsaturated bond).
[0063] In formula (5), R.sup.21 is C4 to C30 linear, branched, or
cyclic, saturated or unsaturated hydrocarbon group which may be
substituted by a hydroxyl group, a carbonyl group, or an amino
group, and R.sup.21 represents preferably a C7 to C22 linear,
branched, or cyclic, saturated or unsaturated hydrocarbon group
which may be substituted by a hydroxyl group. Also preferred are a
C10 to C20 linear or branched alkyl group and a C10 to C20 linear
or branched alkyl group having a hydroxyl group on the carbon atom
bonding to Y in formula (5), wherein when the alkyl is of a
branched type, the branched alkyl is preferably, for example, a
methyl branching fashion alkyl. Specific examples of preferred
alkyl groups include tridecyl, tetradecyl, pentadecyl, hexadecyl,
1-hydroxytridecyl, 1-hydroxypentadecyl, isohexadecyl, and
isostearyl.
[0064] Y represents a methylene group (CH.sub.2), a methine group
(CH), or an oxygen atom.
[0065] Each of X.sup.11, X.sup.12, and X.sup.u is a hydrogen atom,
a hydroxyl group, or an acetoxy group. X.sup.14 is a hydrogen atom,
an acetyl group, or a glyceryl group, or a substituent which forms
an oxo group together with the adjacent oxygen atom. In a preferred
embodiment, all of X.sup.11, X.sup.12, and X.sup.13 are not a
hydroxyl group, or one of X.sup.11, X.sup.12, and X.sup.13 is a
hydroxyl group, and the remaining groups are a hydrogen atom, and
X.sup.14 is a hydrogen atom. When Y is a methine group, one of
X.sup.11 and X.sup.12 is a hydrogen atom, and the other is absent.
When X.sup.14 forms an oxo group, X.sup.13 is absent.
[0066] Each of R.sup.22 and R.sup.23 is a hydrogen atom, a hydroxyl
group, a hydroxymethyl group, or an acetoxymethyl group. R.sup.23
is preferably a hydrogen atom.
[0067] The symbol "a" is a number of 2 or 3. When a is 2, R.sub.1
correspond to R.sup.24 and R.sup.25, and when a is 3, R.sub.1
correspond to R.sup.24, R.sup.25, and R.sup.26.
[0068] Each of R.sup.24, R.sup.25, and R.sup.26 represents a
hydrogen atom, an amidino group, or a linear or branched, saturated
or unsaturated hydrocarbon group optionally having a substituent
selected from the group consisting of a hydroxyl group, a
hydroxyalkoxy group, an alkoxy group, and an acetoxy group and
containing 1 to 8 carbon atoms in total. The hydroxyalkoxy group
which can serve as a substituent of the hydrocarbon group is
preferably a C1 to C7 linear or branched hydroxyalkoxy group. The
alkoxy group is preferably a C1 to C7 linear or branched alkoxy
group. Examples of R.sup.24, R.sup.25, and R.sup.26 include
hydrocarbon groups each having 1 to 8 carbon atoms in total and
being substituted by 1 to 6 substituents. Examples of the
substituents include a hydrogen atom; linear or branched alkyl
groups such as methyl, ethyl, propyl, 2-ethylhexyl, and isopropyl;
alkenyl groups such as vinyl and allyl; an amidino group; hydroxyl
groups such as hydroxymethyl, 2-hydroxyethyl,
1,1-dimethyl-2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl,
2-hydroxy-3-methoxypropyl, 2,3,4,5,6-pentahydroxyhexyl,
1,1-bis(hydroxymethyl)ethyl, 2-(2-hydroxyethoxy)ethyl,
2-methoxyethyl, 1-methyl-2-hydroxyethyl, 3-hydroxypropyl,
3-methoxypropyl, and 1,1-bis(hydroxymethyl)-2-hydroxyethyl;
hydroxyalkoxy groups, and alkoxy groups.
[0069] Among them, more preferred are a hydrogen atom and alkyl
groups each being substituted by 1 to 3 groups selected from the
group consisting of methyl, hydroxyl groups such as 2-hydroxyethyl,
1,1-dimethyl-2-hydroxyethyl, 1,1-bis(hydroxymethyl)ethyl, and
2-(2-hydroxyethoxy)ethyl, and hydroxyalkoxy groups.
[0070] The sphingosine represented by formula (5) is preferably a
naturally occurring sphingosine represented by formula (6), a
synthetic product having the same structure, or a derivative of any
of these (hereinafter referred to as natural-type sphingosine); or
a pseudo-sphingosine represented by formula (7) having a
sphingosine structure (hereinafter referred to as
pseudo-sphingosine).
[0071] (I) Natural-type sphingosine represented by formula (6):
##STR00011##
(wherein R.sup.27 represents a C7 to C19 linear, branched, or
cyclic, saturated or unsaturated hydrocarbon group which may be
substituted by a hydroxyl group; Y.sub.1 represents a methylene
group or a methine group; each of X.sup.15, X.sup.16, and X.sup.17
represents a hydrogen atom, a hydroxyl group, or an acetoxy group;
X.sup.18 represents a hydrogen atom or forms an oxo group together
with the adjacent oxygen atom (wherein when Y.sub.1 is a methine
group, one of X.sup.15 and X.sup.16 is a hydrogen atom, and the
other is absent, and when X.sup.18 forms an oxo group, X.sup.17 is
absent); R.sup.28 represents a hydroxymethyl group or an
acetoxymethyl group; each of the "a" groups of R.sub.2s represents
a hydrogen atom, an amidino group, or a linear or branched,
saturated or unsaturated hydrocarbon group optionally having a
substituent selected from the group consisting of a hydroxyl group,
a hydroxyalkoxy group, an alkoxy group, and an acetoxy group and
containing 1 to 4 carbon atoms in total; a is a number of 2 or 3;
and the broken line represents an optional unsaturated bond).
[0072] R.sup.27 is preferably a C7 to C19 linear, branched, or
cyclic, saturated or unsaturated hydrocarbon group, more preferably
a C13 to C15 linear, saturated or unsaturated hydrocarbon group.
The number "a" is preferably 2. Each of R.sub.2s is preferably a
hydrogen atom or a C1 to C4 linear or branched alkyl group.
[0073] Specific examples of the natural-type sphingosine
represented by formula (6) include sphingosine, dihydrosphingosine,
phytosphingosine, sphingadienine, dehydrosphingosine, and
dehydrophytosphingosine, and N-alkyl derivatives thereof (e.g.,
N-methyl derivatives).
[0074] Regarding these sphingosines, either a natural-type
optically active form (D(+) form) or a non-natural-type optically
active form (L(-) form) may be used. Furthermore, a mixture of a
natural-type form and a non-natural-type form may also be used. The
relative configuration of the aforementioned compound may be ones
of natural-type, of non-natural-type, or of mixed type.
[0075] Examples of preferred sphingosines further include
phytosphingosine (INCI name; 8th Edition) and the compounds
represented by the following formulas.
##STR00012## ##STR00013##
[0076] These compounds may be a natural extract or a synthetic
compound, and a commercial product thereof may be used.
[0077] Examples of the commercial product of natural-type
sphingosine include D-sphingosine (4-sphingenine) (product of
SIGMA-ALDRICH), DS-phytosphingosine (product of DOOSAN), and
phytosphingosine (product of COSMOFERM).
[0078] (II) Pseudo-sphingosine represented by formula (7)
##STR00014##
(wherein R.sup.29 represents a C10 to C22 linear, branched, or
cyclic, saturated or unsaturated hydrocarbon group which may be
substituted by a hydroxyl group; X.sup.19 represents a hydrogen
atom, an acetyl group, or a glyceryl group; each of the "a" groups
of R.sub.3s represents a hydrogen atom, an amidino group, or a
linear or branched, saturated or unsaturated hydrocarbon group
optionally having a substituent selected from the group consisting
of a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an
acetoxy group and containing 1 to 8 carbon atoms in total, and a is
a number of 2 or 3).
[0079] In formula (7), R.sup.29 is preferably a C14 to C20 iso-type
branched alkyl group, more preferably an isostearyl group. The
isostearyl group is preferably an isostearyl group derived from a
raw material oil; i.e., isostearyl alcohol which is a by-product
obtained in production of dimeric acid from a fatty acid
originating from animal or vegetable oil.
[0080] When a is 2, R.sub.3 represents R.sup.30 and R.sup.31,
whereas when a is 3, R.sub.3 represents R.sup.30, R.sup.31, and
R.sup.32.
[0081] Examples of the groups R.sup.30, R.sup.31, and R.sup.32
include a hydrogen atom; linear or branched alkyl groups such as
methyl, ethyl, propyl, 2-ethylhexyl, and isopropyl; alkenyl groups
such as vinyl and allyl; an amidino group; and alkyl groups having
1 to 8 carbon atoms in total and a substituent selected from the
group consisting of hydroxyl groups such as hydroxymethyl,
2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 2-hydroxypropyl,
2,3-dihydroxypropyl, 2-hydroxy-3-methoxypropyl,
2,3,4,5,6-pentahydroxyhexyl, 1,1-bis(hydroxymethyl)ethyl,
2-(2-hydroxyethoxy)ethyl, 2-methoxyethyl, 1-methyl-2-hydroxyethyl,
3-hydroxypropyl, 3-methoxypropyl, and
1,1-bis(hydroxymethyl)-2-hydroxyethyl, hydroxyalkoxy groups, and
alkoxy groups.
[0082] Among them, preferred is a secondary amine in which one of
R.sup.30 and R.sup.31 is a hydrogen atom, and the other is
2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl,
1,1-bis(hydroxymethyl)ethyl, or 2-(2-hydroxyethoxy)ethyl.
[0083] The pseudo-sphingosine is preferably one in which R.sup.29
is an isostearyl group, X.sup.19 is a hydrogen atom, R.sup.30 is a
hydrogen atom, and R.sup.31 is an alkyl group which is substituted
by 1 to 3 substituents selected from the group consisting of
hydroxyl groups such as 2-hydroxyethyl,
1,1-bis(hydroxymethyl)ethyl, 1,1-dimethyl-2-hydroxyethyl, and
2-(2-hydroxyethoxy)ethyl and hydroxyalkoxy groups.
[0084] Specific examples of the pseudo-sphingosine include the
following pseudo-sphingosines (i) to (iv).
##STR00015##
[0085] The sphingosine is preferably sphingosine, phytosphingosine,
or pseudo-sphingosine, more preferably pseud-sphingosine (ii) or
1-(2-hydroxyethylamino)-3-isostearyloxy-2-propanol.
[0086] Examples of the acidic substance which forms salts with the
aforementioned sphingosines, phytosphingosines, and
pseudo-sphingosines include acidic amino acids such as glutamic
acid and aspartic acid; inorganic acids such as phosphoric acid and
hydrochloric acid; monocarboxylic acids such as acetic acid;
dicarboxylic acids such as succinic acid; and hydroxycarboxylic
acids such as citric acid, lactic acid, and malic acid. Among the
aforementioned salts, salts of sphingosines, phytosphingosines, and
pseudo-sphingosines (pseudo-sphingosine (ii),
1-(2-hydroxyethylamino)-3-isostearyloxy-2-propanol) with succinic
acid, lactic acid, and glutamic acid are preferred, with glutamic
acid salts of sphingosines, phytosphingosines, and
pseudo-sphingosines being more preferred.
[0087] As ingredient (D), an anionic surfactant or a sphingosine
salt is preferably used, since repulsion between electric charges
results in retention of a large amount of water in interlayer
spaces of the lamellar structure, leading to high water retention.
Among the anionic surfactant and the sphingosine salt, preferred
are sodium methyl stearoyl taurate (N-stearoyl-N-methyltaurine
sodium salt), sodium polyoxyethylene stearyl ether phosphate,
arginine N-stearoyl-L-glutamate, phytosphingosine glutamic acid
salt, and pseudo-sphingosine glutamic acid salt, since these
compounds form a stable emulsion in a small amount of addition
thereof.
[0088] One or more species of ingredient (D) may be used. The
content of ingredient (D) is 0.00012 to 10 wt. %. Preferably, the
content of ingredient (D) is 0.01 to 7 wt. %, more preferably 0.2
to 3 wt. %, in the total composition, since the interlayer spacing
of the lamellar structure formed from ingredients (A), (B), and (C)
can be increased, to thereby form such a structure that a large
amount of water can be retained in interlayer spaces.
Ingredient (E)
[0089] The sugar alcohol serving as ingredient (E) of the present
invention is selected from the group consisting of erythritol,
threitol, xylitol, and mannitol. Of these, xylitol is
preferred.
[0090] Examples of disaccharide and trisaccharide include
trehalose, galactosylfructose, sucralose, melibiose, raffinose, and
lactose. Of these, trehalose and raffinose are preferred, with
trehalose being more preferred.
[0091] One or more species of ingredient (E) may be used. That is,
sugar alcohol, disaccharide, and/or trisaccharide may be used in
combination.
[0092] The content of ingredient (E) is 0.003 to 15 wt. %, in the
total composition, from the viewpoint of attaining satisfactorily
high water retention.
[0093] In the case of sugar alcohol, the content of sugar alcohol
is preferably 0.003 to 10 wt. %, more preferably 0.01 to 5 wt. %,
even more preferably 0.1 to 3 wt. %, in the total composition.
[0094] In the case of disaccharide or trisaccharide, the content of
disaccharide or trisaccharide is preferably 0.018 to 15 wt. %, more
preferably 0.1 to 10 wt. %, even more preferably 0.5 to 7 wt. %, in
the total composition.
[0095] In the present invention, a preferable relationship of the
weight ratio of ingredients (A), (B), (C) and (E) is
(E)/((A)+(B)+(C)) (by weight) being preferably 0.01 to 5, since
water (bound water and free water) can be firmly retained in
interlayer spaces of the structure formed from ingredients (A),
(B), (C), and (D), thereby remarkably enhancing water
retention.
[0096] In the case where ingredient (E) is sugar alcohol,
(E)/((A)+(B)+(C)) is preferably 0.01 to 3, more preferably 0.125 to
2.5. In the case of disaccharide or trisaccharide,
(E)/((A)+(B)+(C)) is preferably 0.2 or more, more preferably 0.6 to
5.
[0097] Incorporation of ingredient (E) into the composition of the
invention is preferred, since the lamellar structure formed from
ingredients (A), (B), and (C) is stabilized, and the composition
forms, on the dried skin, a soft coating layer having the same
lamellar structure as the intercellular lamellar structure, whereby
the skin water retention can be enhanced, to thereby provide users
with long-lasting moistness.
[0098] (D)/((A)+(B)+(C)) is preferably 0.04 to 1, more preferably
0.04 to 0.5, since ingredient (C) permeability can be enhanced,
whereby a moisturizing effect can be attained at the skin surface
and the inside of the skin.
[0099] In the present invention, the composition preferably has an
ingredient (F) (i.e., water) content of 20 to 99.9 wt. %, more
preferably 40 to 95 wt. %, even more preferably 50 to 90 wt. %.
[0100] The composition of the present invention may further contain
other aqueous base materials, for example, a C1 to C4 lower alcohol
such as ethanol or propanol.
[0101] In the present invention, more preferably, the
aforementioned preferred ingredients are employed in combination in
the aforementioned preferred amounts.
[0102] In more preferred embodiment, the composition contains
glyceryl monobehenate or monocetyl glyceryl ether as ingredient
(A), cetanol as ingredient (B), a compound represented by formula
(2) as ingredient (C), stearoylglutamic acid salt or sphingosine
salt as ingredient (D), xylitol as ingredient (E), and water as
ingredient (F).
[0103] The emulsion composition of the present invention may
further contain an oily ingredient. Examples of the oily ingredient
include hydrocarbon oils such as liquid paraffin, squalane, and
petrolatum; ether oils such as cetyl dimethylbutyl ether, ethylene
glycol dioctyl ether, and glycerol monooleyl ether; ester oils such
as octyl dodeyl myristate, isopropyl palmitate, butyl stearate,
di-2-ethylhexyl adipate, neopentyl glycol dicaprate, and
trioctanoin; higher fatty acids such as stearic acid, behenic acid,
and isomyristic acid; vegetable oil such as olive oil; silicone
oils such as dimethylpolysiloxane, cyclic dimethylpolysiloxane,
methylphenylpolysiloxane, amino-modified silicone, carboxy-modified
silicone, alcohol-modified silicone, alkyl-modified silicone,
polyether-modified silicone, and fluorine-modified silicone; and
fluorine-containing oils such as perfluoroalkylethylphosphoric
acid, perfluoroalkylpolyoxyethylenephosphoric acid,
perfluoropolyether, and polytetrafluoroethylene. The composition of
the invention preferably has an oily ingredient content of 0 to 20
wt. % in the total composition.
[0104] The emulsion composition of the present invention may
further contain active ingredients or additives which are employed
in typical cosmetics. Examples of such ingredients and additives
include water-soluble vitamins such as ascorbic acid, nicotinamide,
and nicotinic acid; animal and vegetable extracts such as
Phellodendoron Amurense extract, licorice extract, aloe extract,
horsetail extract, tea extract, cucumber extract, clove extract,
ginseng extract, witch hazel extract, placenta extract, seaweed
extract, horse chestnut extract, Japanese citron (Yuzu) extract,
thujopsis dolabrata extract, royal jelly extract, eucalyptus
extract, and thujopsis dolabrata extract solution; bases such as
potassium hydroxide, sodium hydroxide, triethanolamine, and sodium
carbonate; acids such as citric acid, tartaric acid, lactic acid,
phosphoric acid, succinic acid, and adipic acid; and thickening
agents such as carboxyvinyl polymer, sodium arginate, carrageenan,
carboxymethylcellulose, hydroxyethylcellulose, guar gum, xanthan
gum, carboxymethylchitosan, sodium hyaluronate, oxazoline-modified
silicone, N,N-dimethylaminoethyl methacrylate diethylsulfate
salt-N,N-dimethylacrylamide-polyethylene glycol dimethacrylate
copolymer.
[0105] The emulsion composition of the present invention may be
produced through any of production methods (1) to (3):
[0106] Production method (1): emulsification through mixing
ingredients (A) to (D) (in the case of the composition containing
an oily ingredient, a mixture of ingredients (A) to (D) and the
oily ingredient) with an aqueous phase including ingredients (E)
and (F);
[0107] Production method (2): emulsification through mixing
ingredients (A) to (E) (in the case of the composition containing
an oily ingredient, a mixture of ingredients (A) to (E) and the
oily ingredient) with an aqueous phase including ingredient (F);
and
[0108] Production method (3): emulsification through mixing a
mixture of ingredients (A) to (D) (in the case of the composition
containing an oily ingredient, a mixture of ingredients (A) to (D)
and the oily ingredient) and a portion of ingredient (E) with an
aqueous phase including the remaining ingredient (E) and ingredient
(F).
[0109] Production method (2) is more preferred as compared with
production method (1), since the emulsion composition produced
through production method (2) has higher water retention.
[0110] The thus-produced emulsion composition assumes .alpha.-gel
(.alpha.-type crystal), with deposition of .gamma.-type crystals
being prevented. .alpha.-Gel can be identified through X-ray
structure analysis. .alpha.-Type structure is a hexagonal crystal
structure type, in which a lipophilic group is arranged normal to
the hydrophilic group layer, with one characteristic diffraction
peak at a Bragg angle of 21 to 23.degree..
[0111] Also, the emulsion composition of the present invention is
an O/W-type emulsion composition and is suited for producing, for
example, cosmetics such as skin lotion, milky lotion, cream, and
gel, or an agent for skin external use.
EXAMPLES
Examples 1 to 10 and Comparative Examples 1 to 8
[0112] O/W emulsion compositions having formulations shown in
Tables 1 and 2 were produced. The thus-produced compositions were
subjected to X-ray structural analysis and remaining water content
measurement. Also, the film formability of each composition was
assessed. The results are also shown in Tables 1 and 2.
[0113] Through observation under a transmission electron
microscope, the coating films produced in the Examples were found
to have a lamellar structure.
Production Method
Production Method (1)
[0114] Phase I ingredients (mixture containing ingredients (A) to
(D)) were heated and mixed at 80 to 95.degree. C. Under
propeller-stirring (300 rpm), phase II ingredients (mixture
containing ingredients (E) and (F)), which had been heated to 80 to
95.degree. C., were added to the phase I ingredients, to thereby
form an emulsion. The emulsion was gradually cooled to 25.degree.
C., to thereby yield an O/W emulsion composition.
Evaluation Method
(1) X-Ray Structure Analysis
[0115] The crystal structure of each of the thus-prepared O/W
emulsion compositions was determined from wide angle X-ray
diffraction peaks (2.theta.=10 to 30.degree.) according to Wilson's
& Ott's method (Wilson, D. A. and Ott, E., J. Chem. Phys., 2,
231-238(1934)).
(2) Remaining Water Content Measurement:
[0116] Each O/W emulsion composition (2 g) was spread on a metal
tray (6.times.6 cm), to thereby form a layer having a uniform
thickness. Under constant temperature and humidity conditions
(25.degree. C., 40%), the weight of the layer was monitored. The
measurements were plotted to time. As shown in FIG. 1, the drawn
curve was bent at two points. When a lamellar film is formed, the
subsequent change in weight will be minimized. The weight value at
the crossing between lines 1 and 2 in FIG. 1 was employed as the
remaining water content. The water content of the solid of each
composition (preparation) was calculated by the following equation
(the solid containing ingredients (A) to (E)):
Water content(%)=(remaining water content/(solid content+remaining
water content)).times.100
(3) Film Formability:
[0117] Each agent (5 g) was placed in a Petri dish (diameter: 5 cm)
made of Teflon (registered trademark), and uniformly spread. The
agent was dried for two days, and the state of the film was
observed.
A: Formation of soft coating film B: Formation of hard and fragile
coating film C: Formation of coating film failed
TABLE-US-00001 TABLE 1 Ex. Comp. Ex. Ingredients (wt. %) 1 2 3 4 1
2 3 4 Phase I D 1-(2-Hydroxyethylamino)-3- 0.2 0.2 0.2 0.2 0.2 0.2
0.2 0.2 isostearyloxy-2-propanol C Pseudo-ceramide* 3 3 3 3 3 3 3 3
B Cetanol 1 1 1 1 1 1 1 1 A Monocetyl glyceryl ether 1 1 1 1 1 1 1
1 Phase II F Water bal. bal. bal. bal. bal. bal. bal. bal.
L-Glutamic acid 0.12 0.12 0.12 0.12 0.12 0.12 0.12 0.12 E
Erythritol 1 Threitol 1 Xylitol 1 Mannitol 1 Sorbitol 1 Glycerin 1
Glucose 1 Total 100 100 100 100 100 100 100 100 ((A) + (B))/((A) +
(B) + (C)) 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 (A)/((A) + (B)) 0.5 0.5
0.5 0.5 0.5 0.5 0.5 0.5 (E)/((A) + (B) + (C)) 0.2 0.2 0.2 0.2 -- --
-- -- X-ray structure analysis .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type Remaining water content (%) 67.0 66.8 70.0 66.0 65.2
61.9 59.5 62.3 Film formability A A A A B B B B
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
TABLE-US-00002 TABLE 2 Ex. Comp. Ex. Ingredients (wt. %) 5 6 7 8 9
10 5 6 7 8 Phase I D 1-(2-Hydroxyethylamino)- 0.2 0.2 0.2 0.2 0.2
0.2 0.2 0.2 0.2 0.2 3-isostearyloxy-2-propanol C Pseudo-ceramide* 3
3 3 3 3 3 3 3 3 3 B Cetanol 1 1 1 1 1 1 1 1 1 1 A Monocetyl
glyceryl ether 1 1 1 1 1 1 1 1 1 1 Phase F Water bal. bal. bal.
bal. bal. bal. bal. bal. bal. bal. II L-Glutamic acid 0.12 0.12
0.12 0.12 0.12 0.12 0.12 0.12 0.12 0.12 E Trehalose 5 Raffinose 5
Lactose 5 Galactosylfructose 5 Sucralose 5 Melibiose 5 Glycerin 5
Glucose 5 Trimethylglycine 5 Total 100 100 100 100 100 100 100 100
100 100 ((A) + (B))/((A) + (B) + (C)) 0.4 0.4 0.4 0.4 0.4 0.4 0.4
0.4 0.4 0.4 (A)/((A) + (B)) 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5
(E)/((A) + (B) + (C)) 1.0 1.0 1.0 1.0 1.0 1.0 -- -- -- -- X-ray
structure analysis .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .alpha.-type Remaining water content (%) 72.15 71.21
71.21 70.72 70.28 71.44 65.20 53.18 61.50 59.41 Film formability A
A A A A A B B B C
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 11 and Comparative Examples 9 to 11
[0118] In a manner similar to that employed in Examples 1 to 10,
O/W emulsion compositions having formulations shown in Table 3 were
produced. The small angle X-ray scattering intensity of each
composition was monitored. The intensity was compared with that of
the composition of Comparative Example 9. Table 3 shows the
results.
TABLE-US-00003 TABLE 3 Ex. Comp. Ex. Ingredients (wt. %) 11 9 10 11
Phase D 1-(2- 0.4 0.4 0.4 0.4 I Hydroxyethylamino)-3-
isostearyloxy-2-propanol C Pseudo-ceramide* 6 6 6 6 B Cetanol 2 2 2
2 A Monocetyl glyceryl 2 2 2 2 ether Phase F Water bal. bal. bal.
bal. II L-Glutamic acid 0.24 0.24 0.24 0.24 E Xylitol 3
Trimethylglycine 3 Glycerin 3 Total 100 100 100 100 ((A) +
(B))/((A) + (B) + (C)) 0.4 0.4 0.4 0.4 (A)/((A) + (B)) 0.5 0.5 0.5
0.5 (E)/((A) + (B) + (C)) 0.3 -- -- -- Small angle X-ray scattering
intensity increase no no change change
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
[0119] As is clear from Table 3, the composition of Example 11
exhibited an increase in small angle X-ray scattering intensity,
indicating that the lamellar structure has high order.
Examples 12 to 17 and Comparative Examples 12 to 21
[0120] In a manner similar to that employed in Examples 1 to 10,
O/W emulsion compositions having formulations shown in Table 4 were
produced. The thus-produced compositions were subjected to X-ray
structural analysis and evaluated in terms of remaining water
content and film formability. The skin permeability of each
composition and lasting of moist skin attained by the composition
were assessed. The results are also shown in Table 4.
Evaluation Methods
Feeling Upon Use of the Composition (Skin Permeability/Lasting of
Moist Skin)
[0121] The emulsion compositions were tested by 10 expert
panelists. Specifically, each emulsion composition (0.5 to 0.6 g)
was applied to the face of each panelist. The "skin permeation
sensation" immediately after application of the composition and
"lasting of moist skin" 10 hours after application thereof were
sensorily evaluated by the panelists. The evaluation was scores
represented by the number of panelists who gave a rating of
"satisfactory."
TABLE-US-00004 TABLE 4 Ex. Ingredients (wt. %) 12 13 14 15 16 17
Phase I D 1-(2-Hydroxyethylamino)-3- 0.2 0.2
isostearyloxy-2-propanol D Stearoylglutamic acid 0.5 0.5 D Sodium
methyl stearoyl taurate 0.5 D Polyoxyethylene(20) sorbitan 2
monostearate (HLB 14.9) Hydrogenated lecithin 1 C Pseudo-ceramide*
2 2.5 3 1 1 1 Stearic acid B Cetanol 1 1 1 1.5 1 3 B Cholesterol A
Glyceryl monostearate A Glyceryl monobehenate 1.5 1 A Monostearyl
glyceryl ether 2.5 3 A Monocetyl glyceryl ether 2 A Sorbitan
monostearate 1 A Sorbitan distearate 0.5 Phase II F Water bal. bal.
bal. bal. bal. bal. L-Arginine 0.35 L-Glutamic acid 0.12 0.12 E
Xylitol 1 1 1 1 1 1 Total 100 100 100 100 100 100 ((A) + (B))/((A)
+ (B) + (C)) 0.6 0.5 0.4 0.8 0.8 0.8 (A)/((A) + (B)) 0.67 0.6 0.5
0.63 0.75 0.3 (E)/((A) + (B) + (C)) 0.2 0.2 0.2 0.2 0.2 0.2 X-ray
structure analysis .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type Remaining water content (%)
64.6 63.3 61.5 59.9 57.7 60.2 Film formability A A A A A A
Permeation sensation 10 10 9 9 8 8 Lasting of moist skin 10 9 9 8 7
8 Comp Ex. Ingredients (wt. %) 12 13 14 15 16 17 18 19 20 21 Phase
I D 1-(2-Hydroxyethylamino)- 0.2 0.2 0.2 0.2
3-isostearyloxy-2-propanol D Stearoylglutamic acid 0.5 D Sodium
methyl stearoyl 0.5 0.3 taurate D Polyoxyethylene(20) 2 2.3
sorbitan monostearate (HLB 14.9) Hydrogenated lecithin 1 1.5 C
Pseudo-ceramide* 2 2.5 3 1 1 3 Stearic acid 3 B Cetanol 1 1 1 1.5 1
2.5 2 1.8 2 B Cholesterol 2.5 1 A Glyceryl monostearate 3.2 A
Glyceryl monobehenate 1.5 A Monostearyl glyceryl ether 2.5 3 4 A
Monocetyl glyceryl ether 2 A Sorbitan monostearate 1 A Sorbitan
distearate Phase II F Water bal. bal. bal. bal. bal. bal. bal. bal.
bal. bal. L-Arginine 0.35 L-Glutamic acid 0.12 0.12 0.12 0.12 E
Xylitol 1 1 1 1 1 Total 100 100 100 100 100 100 100 100 100 100
((A) + (B))/((A) + (B) + (C)) 0.6 0.5 0.4 0.8 0.8 1 0.4 1 0.4 1
(A)/((A) + (B)) 0.67 0.6 0.5 0.63 0.75 -- -- 0.64 -- 0.8 (E)/((A) +
(B) + (C)) -- -- -- -- -- 0.2 0.2 0.2 0.2 0.2 X-ray structure
analysis .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .gamma.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type Remaining water content (%) 59.1 58.7 57.1 57 55.1
10.8 32.6 52.6 20.8 16.3 Film formability B B B B B C B B B C
Permeation sensation 7 6 8 7 7 3 6 7 5 1 Lasting of moist skin 6 4
5 4 4 3 5 4 3 2
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Examples 18 to 53 and Comparative Examples 22 to 33
[0122] In a manner similar to that employed in Examples 1 to 10,
O/W emulsion compositions having formulations shown in Tables 5 to
9 were produced. The thus-produced compositions were subjected to
X-ray structural analysis and evaluated in terms of remaining water
content. The skin permeability and lasting of moist skin attained
by each composition were assessed. The results are also shown in
Tables 5 to 9.
TABLE-US-00005 TABLE 5 Ex. Ingredients (wt. %) 18 19 20 21 22 Phase
D 1-(2-Hydroxyethylamino)-3- 0.2 0.2 I isostearyloxy-2-propanol D
Stearoylglutamic acid 0.5 D Sorium methyl stearoyl taurate 0.5 D
Polyoxyethylene(20) sorbitan 2 monostearate (HLB 14.9) Hydrogenated
lecithin 1 C Pseudo-ceramide* 2 2.5 3 1 1 Stearic acid B Cetanol 1
1 1 1.5 1 B Cholesterol A Glyceryl monostearate A Glyceryl
monobehenate 1.5 A Monostearyl glyceryl ether 2.5 3 A Monocetyl
glyceryl ether 2 A Sorbitan monostearate 1 Phase F Water bal. bal.
bal. bal. bal. II L-Arginine 0.35 L-Glutamic acid 0.12 0.12 E
Trehalose 5 5 5 5 5 Total 100 100 100 100 100 ((A) + (B))/((A) +
(B) + (C)) 0.6 0.5 0.4 0.8 0.8 (A)/((A) + (B)) 0.7 0.6 0.5 0.6 0.8
(E)/((A) + (B) + (C)) 1.0 1.0 1.0 1.0 1.0 X-ray structure analysis
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
Remaining water content (%) 67.53 67.58 66.25 62.97 60.50
Permeation sensation 9 9 9 8 8 Lasting of moist skin 10 9 9 8 6
Comp. Ex. Ingredients (wt. %) 22 23 24 25 26 27 28 29 30 31 Phase D
1-(2-Hydroxyethylamino)-3- 0.2 0.2 0.2 0.2 I
isostearyloxy-2-propanol D Stearoylglutamic acid 0.5 D Sorium
methyl stearoyl 0.5 0.3 taurate D Polyoxyethylene(20) sorbitan 2
2.3 monostearate (HLB 14.9) Hydrogenated lecithin 1 1.5 C
Pseudo-ceramide* 2 2.5 3 1 1 3 Stearic acid 3 B Cetanol 1 1 1 1.5 1
2.5 2 1.8 2 B Cholesterol 2.5 1 A Glyceryl monostearate 3.2 A
Glyceryl monobehenate 1.5 A Monostearyl glyceryl ether 2.5 3 4 A
Monocetyl glyceryl ether 2 A Sorbitan monostearate 1 Phase F Water
bal. bal. bal. bal. bal. bal. bal. bal. bal. bal. II L-Arginine
0.35 L-Glutamic acid 0.12 0.12 0.12 0.12 E Trehalose 5 5 5 5 5
Total 100 100 100 100 100 100 100 100 100 100 ((A) + (B))/((A) +
(B) + (C)) 0.6 0.5 0.4 0.8 0.8 -- 0.7 1.0 -- 1.0 (A)/((A) + (B))
0.7 0.6 0.5 0.6 0.8 -- -- 0.6 -- 0.8 (E)/((A) + (B) + (C)) -- -- --
-- -- 1.0 1.7 1.0 2.5 1.0 X-ray structure analysis .alpha.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .gamma.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type Remaining water
content (%) 59.13 58.65 57.13 56.99 55.10 24.32 41.35 56.04 28.50
23.04 Permeation sensation 7 6 8 7 7 3 6 2 4 7 Lasting of moist
skin 5 5 4 4 4 8 4 1 4 1
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
TABLE-US-00006 TABLE 6 Comp. Ex. Ex. Ingredients (wt. %) 23 24 25
26 27 28 29 30 31 32 Phase D 1-(2-Hydroxyethylamino)-3- 0.13 0.25
0.1 0.2 2 0.25 0.2 0.4 1.2 0.2 I isostearyloxy-2-propanol C
Pseudo-ceramide* 2.8 4 1 3 0.5 0.1 0.1 0.2 0.2 11 B Cetanol 0.45
1.6 0.5 1 1 0.1 1 0.4 0.4 0.5 A Glyceryl monobehenate 0.05 0.55 0.5
1 0.5 0.3 1 0.4 0.4 0.05 Phase F Water bal. bal. bal. bal. bal.
bal. bal. bal. bal. bal. II L-Glutamic acid 0.078 0.15 0.06 0.12
1.2 0.15 0.12 0.24 0.72 0.12 E Xylitol 0.04 0.8 1 1 3 1.25 1 3 3
0.04 Total 100 100 100 100 100 100 100 100 100 100 ((A) + (B))/((A)
+ (B) + (C)) 0.15 0.35 0.5 0.4 0.8 0.8 0.95 0.8 0.8 0.05 (A)/((A) +
(B)) 0.1 0.26 0.5 0.5 0.33 0.75 0.5 0.5 0.5 0.09 (E)/((A) + (B) +
(C)) 0.01 0.13 0.5 0.2 1.5 2.5 0.48 3.0 3.0 0.003 X-ray structure
analysis .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.gamma.-type Remaining water content (%) 58.1 59.5 62.9 61.5 65.3
60.6 55.0 57.1 58.2 13.4 Film formability A A A A A A A A A C
Permeation sensation 7 8 9 10 8 9 8 7 7 4 Lasting of moist skin 7 9
10 10 10 8 7 7 8 1
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
TABLE-US-00007 TABLE 7 Comp. Ex. Ex. Ingredients (wt. %) 32 33 34
35 36 37 38 39 40 33 Phase D 1-(2-Hydroxyethylamino)-3- 0.13 0.25
0.1 0.5 2 0.25 0.2 0.2 1.2 0.2 I isostearyloxy-2-propanol C
Pseudo-ceramide* 2.8 4 1 3 0.5 0.1 0.1 0.2 0.2 11 B Cetanol 0.45
1.6 0.5 1 1 0.1 1 0.4 0.4 0.5 A Glyceryl monobehenate 0.05 0.55 0.5
1 0.5 0.3 1 0.4 0.4 0.05 Phase F Water bal. bal. bal. bal. bal.
bal. bal. bal. bal. bal. II L-Glutamic acid 0.078 0.15 0.06 0.12
1.2 0.15 0.12 0.12 0.72 0.12 E Trehalose 0.7 3.7 2 4 3 2.5 2 4 3
0.04 Total 100 100 100 100 100 100 100 100 100 100 ((A) + (B))/((A)
+ (B) + (C)) 0.15 0.35 0.5 0.4 0.8 0.8 0.95 0.8 0.8 0.07 (A)/((A) +
(B)) 0.1 0.26 0.5 0.5 0.33 0.75 0.5 0.5 0.5 0.09 (E)/((A) + (B) +
(C)) 0.21 0.60 1.0 0.8 1.5 5.0 0.95 4.0 3.0 0.003 X-ray structure
analysis .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.gamma.-type Remaining water content (%) 57.4 60.2 63.3 67.2 66.9
61.7 55.5 62.5 61.1 14.8 Film formability A A A A A A A A A C
Permeation sensation 7 8 10 10 8 9 7 7 7 5 Lasting of moist skin 7
9 10 10 9 8 7 8 8 3
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
TABLE-US-00008 TABLE 8 Ex. Ingredients (wt. %) 41 42 43 44 45 Phase
I D 1-(2-Hydroxyethylamino)-3- 0.01 0.2 3 7 10
isostearyloxy-2-propanol C Pseudo-ceramide* 0.05 0.1 5 7 10 B
Cetanol 0.05 0.1 3 7 10 A Glyceryl monobehenate 0.05 0.3 3 7 10
Phase F Water bal. bal. bal. bal. bal. II L-Glutamic acid 0.006
0.12 1.8 4.2 6 E Xylitol 0.01 0.1 3 5 10 Total 100 100 100 100 100
((A) + (B))/((A) + (B) + (C)) 0.67 0.8 0.55 0.67 0.67 (A)/((A) +
(B)) 0.5 0.75 0.5 0.5 0.5 (E)/((A) + (B) + (C)) 0.07 0.2 0.27 0.24
0.33 X-ray structure analysis .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type Remaining water content (%)
60.3 65.1 67.8 60.5 54.3 Film formability A A A A B Permeation
sensation 7 9 9 9 7 Lasting of moist skin 9 9 10 8 6
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
TABLE-US-00009 TABLE 9 Ex. Ingredients (wt. %) 46 47 48 49 50 51 52
53 Phase I D 1-(2-Hydroxyethylamino)-3- 0.01 0.2 1 3 3 7 3 7
isostearyloxy-2-propanol C Pseudo-ceramide* 0.05 0.1 1 5 5 7 5 10 B
Cetanol 0.05 0.1 1 3 3 7 3 10 A Glyceryl monobehenate 0.05 0.3 1 3
5 7 3 10 Phase F Water bal. bal. bal. bal. bal. bal. bal. bal. II
L-Glutamic acid 0.006 0.12 0.6 1.8 1.8 4.2 1.8 4.2 E Trehalose 0.1
0.5 3 7 10 10 15 6 Total 100 100 100 100 100 100 100 100 ((A) +
(B))/((A) + (B) + (C)) 0.67 0.8 0.67 0.55 0.62 0.67 0.55 0.67
(A)/((A) + (B)) 0.5 0.75 0.5 0.5 0.63 0.5 0.5 0.5 (E)/((A) + (B) +
(C)) 0.67 1.0 1.0 0.64 0.77 0.48 1.36 0.2 X-ray structure analysis
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
.alpha.-type .alpha.-type .alpha.-type Remaining water content (%)
65.8 67.7 69.3 68.0 67.5 61.2 57.3 55.4 Film formability A A A A A
A A B Permeation sensation 7 10 10 10 8 7 6 7 Lasting of moist skin
7 9 10 9 9 8 7 5
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Examples 54 to 56
[0123] O/W emulsion compositions having formulations shown in Table
10 were produced through production method (2). The thus-produced
emulsion compositions were subjected to X-ray structural analysis
and evaluated in terms of remaining water content and film
formability. The skin permeability of each composition and lasting
of moist skin attained by each composition were assessed. The
results are also shown in Table 10.
[0124] Emulsion compositions having the same formulations as those
of Examples 54 to 56 were also produced through production method
(1) (Examples 30, 3, and 5). The evaluation results thereof are
also shown in Table 10.
Production Method (2)
[0125] Phase I ingredients (mixture containing ingredients (A) to
(E)) were heated and mixed at 80 to 95.degree. C. Under
propeller-stirring (300 rpm), phase II ingredient (aqueous phase
containing ingredient (F)), which had been heated to 80 to
95.degree. C., was added to the phase I ingredients, to thereby
form an emulsion. The emulsion was gradually cooled to 25.degree.
C., to thereby yield an O/W emulsion composition.
TABLE-US-00010 TABLE 10 Ex. Ingredients (wt. %) 54 30 55 3 56 5
Phase I D 1-(2-Hydroxyethylamino)-3- 0.4 0.4 0.2 0.2 0.2 0.2
isostearyloxy-2-propanol C Pseudo-ceramide* 0.2 0.2 3 3 3 3 B
Cetanol 0.4 0.4 1 1 1 1 A Glyceryl monobehenate 0.4 0.4 A Monocetyl
glyceryl ether 1 1 1 1 E Xylitol 3 1 E Trehalose 5 Phase F Water
bal. bal. bal. bal. bal. bal. II L-Glutamic acid 0.24 0.24 0.12
0.12 0.12 0.12 E Xylitol 3 1 E Trehalose 5 Total 100 100 100 100
100 100 ((A) + (B))/((A) + (B) + (C)) 0.8 0.8 0.4 0.4 0.4 0.4
(A)/((A) + (B)) 0.5 0.5 0.5 0.5 0.5 0.5 (E)/((A) + (B) + (C)) 3.0
3.0 0.2 0.2 0.2 1.0 X-ray structure analysis .alpha.-type
.alpha.-type .alpha.-type .alpha.-type .alpha.-type .alpha.-type
Remaining water content (%) 59.6 57.1 71.0 70.0 74.6 72.15 Film
formability A A A A A A Permeation sensation 8 7 10 8 10 7 Lasting
of moist skin 9 7 10 9 10 9
*N-(hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 57
Skin Lotion
[0126] In a manner similar to that employed in Examples 1 to 10, an
O/W emulsion composition (skin lotion) having a formulation shown
in Table 11 was produced. X-ray structural analysis of the
composition was performed. Film formability, and skin permeability
of the composition, and lasting of moist skin attained by the
composition were assessed. The results are also shown in Table
11.
TABLE-US-00011 TABLE 11 (Ingredients) (wt. %) Phase I D
1-(2-Hydroxyethylamino)-3- 0.2 isostearyloxy-2-propanol D
Phytosphingosine 0.01 C Pseudo-ceramide* 0.5 C CERAMIDE 2 0.1 B
Cetanol 0.2 A Monostrearyl glyceryl ether 0.2 Glycerin 5.0 Phase F
Water bal. II Methylparaben q.s. E Xylitol 1.0 E Erythritol 1.0
Hydroxyethylcellulose 0.01 Eucalyptus extract 0.1 Thujopsis
dolabrata extract 0.1 Altheae extract 0.1 Seaweed extract 0.1
L-Glutamic acid 0.1 Total 100 ((A) + (B))/((A) + (B) + (C)) 0.40
(A)/((A) + (B)) 0.50 (E)/((A) + (B) + (C)) 1.98 X-ray structure
analysis .alpha.-type Film formability A Permeation sensation 8
Lasting of moist skin 8
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 58
Milky Lotion
[0127] In a manner similar to that employed in Examples 1 to 10, an
O/W emulsion composition (milky lotion) having a formulation shown
in Table 12 was produced. X-ray structural analysis of the
composition was performed. The film formability and skin
permeability of the composition, and lasting of moist skin attained
by the composition were assessed. The results are also shown in
Table 12.
TABLE-US-00012 TABLE 12 (Ingredients) (wt. %) Phase I D Sodium
polyoxyethylene(4) lauryl ether 0.2 phosphate D Polyoxyethylene(20)
sorbitan monostearate 0.3 (HLB 14.9) C Pseudo-ceramide* 1.0 C
CERAMIDE 2 0.1 B Cetanol 1.0 A Sorbitan monostearate 0.2 Squalane
4.0 Dimethylpolysiloxane 5.0 Glycerin 10.0 Phase F Water bal. II D
Sodium methyl stearoyl taurate 0.3 Methylparaben q.s.
Phenoxyethanol q.s. Sodium hydroxide q.s. Carboxyvinyl polymer 0.2
Xanthan gum 0.1 E Erythritol 1.0 E Mannitol 0.5 1,3-Butanediol 2.0
Ginger extract 0.1 Yuzu extract 0.1 Total 100 ((A) + (B))/((A) +
(B) + (C)) 0.52 (A)/((A) + (B)) 0.17 (E)/((A) + (B) + (C)) 0.65
X-ray structure analysis .alpha.-type Film formability A Permeation
sensation 8 Lasting of moist skin 9
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 59
Semi-Transparent Gel
[0128] In a manner similar to that employed in Examples 1 to 10, an
O/W emulsion composition (semi-transparent gel) having a
formulation shown in Table 13 was produced. X-ray structural
analysis of the composition was performed. The film formability and
skin permeability of the composition, and lasting of moist skin
attained by the composition were assessed. The results are also
shown in Table 13.
TABLE-US-00013 TABLE 13 (Ingredients) (wt. %) Phase I D
Stearoylglutamic acid 0.5 C Pseudo-ceramide* 2.0 C CERAMIDE 2 0.1 B
Cetanol 1.0 B Stearyl alcohol 0.5 A Monostrearyl glyceryl ether 0.5
A Glyceryl monobehenate 2.0 Glycerin 5.0 Phase F Water bal. II
Methylparaben q.s. E Xylitol 0.7 E Threitol 0.3 Carboxyvinyl
polymer 0.3 Eucalyptus extract 0.1 Thujopsis dolabrata extract 0.1
Altheae extract 0.1 Seaweed extract 0.1 L-Arginine q.s. Total 100
((A) + (B))/((A) + (B) + (C)) 0.66 (A)/((A) + (B)) 0.63 (E)/((A) +
(B) + (C)) 0.16 X-ray structure analysis .alpha.-type Film
formability A Permeation sensation 9 Lasting of moist skin 9
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 60
Cream
[0129] In a manner similar to that employed in Examples 1 to 10, an
O/W emulsion composition (cream) having a formulation shown in
Table 14 was produced. X-ray structural analysis of the composition
was performed. The film formability and skin permeability of the
composition, and lasting of moist skin attained by the composition
were assessed. The results are also shown in Table 14.
TABLE-US-00014 TABLE 14 (Ingredients) (wt. %) Phase I D Sodium
stearoylglutamate 0.5 C Pseudo-ceramide* 3.5 C CERAMIDE 3 0.5 B
Cetanol 1.0 B Cholesterol 0.1 A Glyceryl monobehenate 1.5 A
Monostearoyl glyceryl ether 0.5 Stearic acid 0.1
Dimethylpolysiloxane 5.0 Olive oil 5.0 Squalane 5.0 Dicapryl
carbonate 0.5 Petrolatum 1.0 Cholesteryl isostearate 1.0 Sorbitol
2.0 Glycerin 15.0 Phase F Water bal. II D Sodium methyl stearoyl
taurate 0.3 Methylparaben 0.3 Phenoxyethanol 0.2 Xanthan gum 0.2 1%
Tuberosa polysaccharide 2.0 E Xylitol 1.0 Total 100 ((A) +
(B))/((A) + (B) + (C)) 0.44 (A)/((A) + (B)) 0.65 (E)/((A) + (B) +
(C)) 0.14 X-ray structure analysis .alpha.-type Film formability A
Permeation sensation 9 Lasting of moist skin 10
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 61
Skin Lotion
[0130] Phase I ingredients were heated and mixed at 80 to
95.degree. C. Under propeller-stirring (300 rpm), phase II
ingredients, which had been heated to 80 to 95.degree. C., were
added to the phase I ingredients, to thereby form an emulsion. The
emulsion was gradually cooled to 25.degree. C., and phase III
ingredients (25.degree. C.) were added to the cooled emulsion, to
thereby yield an O/W emulsion composition (skin lotion) having a
formulation of Table 15. X-ray structural analysis of the
composition was performed. The film formability and skin
permeability of the composition, and lasting of moist skin attained
by the composition were assessed. The results are also shown in
Table 15.
TABLE-US-00015 TABLE 15 (Ingredients) (wt. %) Phase A Monostrearyl
glyceryl ether 0.25 I B Cetanol 0.15 C Pseudo-ceramide* 0.6 D
1-(2-Hydroxyethylamino)-3- 0.2 isostearyloxy-2-propanol Glycerin
5.0 Phase F Water bal. II L-Glutamic acid 0.07 Methylparaben 0.2
Phase Water 5.0 III Ethanol 3.0 1,3-Butylene glycol 3.0 E Trehalose
3.0 E Raffinose 2.0 Thujopsis dolabrata extract 0.5 Eucalyptus
extract 0.5 Amidinoproline 0.2 Total 100 ((A) + (B))/((A) + (B) +
(C)) 0.4 (A)/((A) + (B)) 0.63 (E)/((A) + (B) + (C)) 5.0 X-ray
structure analysis .alpha.-type Film formability A Permeation
sensation 8 Lasting of moist skin 9
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 62
Essence Lotion
[0131] Phase I ingredients were heated and mixed at 80 to
95.degree. C. Under propeller-stirring (300 rpm), phase II
ingredients, which had been heated to 80 to 95.degree. C., were
added to the phase I ingredients, to thereby form an emulsion. The
emulsion was gradually cooled to 25.degree. C., and phase III
ingredients (25.degree. C.) were added to the cooled emulsion, to
thereby yield an O/W emulsion composition (essence lotion) having a
formulation of Table 16. X-ray structural analysis of the
composition was performed. The film formability and skin
permeability of the composition, and lasting of moist skin attained
by the composition were assessed. The results are also shown in
Table 16.
TABLE-US-00016 TABLE 16 (Ingredients) (wt. %) Phase A Monocetyl
glyceryl ether 0.7 I B Cetanol 0.6 C Pseudo-ceramide* 2.0 D
Stearoylglutamic acid 0.2 E Lactose 2.0 E Sucralose 2.0 Phase F
Water bal. II L-Arginine 0.14 Methylparaben 0.2 Phase
Dimethylpolysiloxane 3.0 III Carboxyvinyl polymer 0.1 F Water 15.0
Tuberosa polysaccharide liq. 5.0 Dipropylene glycol 5.0 Horse
chestnut extract 0.2 Chamomile extract 0.2 Yuzu extract 0.2 Clove
extract 0.2 Altheae extract 0.2 Tea extract 0.2 Lemon extract 0.2
Seaweed extract 0.1 Total 100 ((A) + (B))/((A) + (B) + (C)) 0.39
(A)/((A) + (B)) 0.54 (E)/((A) + (B) + (C)) 1.21 X-ray structure
analysis .alpha.-type Film formability A Permeation sensation 9
Lasting of moist skin 9
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 63
Milky Lotion
[0132] In a manner similar to that employed in Examples 1 to 10, an
O/W emulsion composition (milky lotion) having a formulation shown
in Table 17 was produced. X-ray structural analysis of the
composition was performed. The film formability and skin
permeability of the composition, and lasting of moist skin attained
by the composition were assessed. The results are also shown in
Table 17.
TABLE-US-00017 TABLE 17 (Ingredients) (wt. %) Phase A Sorbitan
monostearate 0.6 I B Cetanol 0.6 B Stearyl alcohol 0.4 C
Pseudo-ceramide* 2.0 D Polyoxyethylene(40) hydrogenated castor oil
1.0 D Sodium methyl stearoyl taurate 0.3 D Polyoxyethylene(20)
sorbitan monostearate 1.4 (HLB 14.9) Squalane 3.0 Pentaerythritol
tetraoctanoate 3.0 Glyceryl tri(2-ethylhexanoate) 3.0 Cetyl
octanoate 1.0 Glycerin 3.0 E Galactosylfructose 2.5 E Melibiose 2.5
Phase Dimethylpolysiloxane 3.0 II Carboxyvinyl polymer 0.2 F Water
bal. Phenoxyethanol 0.3 Methylparaben 0.1 Potassium hydroxide q.s.
Total 100 ((A) + (B))/((A) + (B) + (C)) 0.44 (A)/((A) + (B)) 0.38
(E)/((A) + (B) + (C)) 1.39 X-ray structure analysis .alpha.-type
Film formability A Permeation sensation 9 Lasting of moist skin 9
*N-(Hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
Example 64
Cream
[0133] In a manner similar to that employed in Examples 1 to 10, an
O/W emulsion composition (cream) having a formulation shown in
Table 18 was produced. X-ray structural analysis of the composition
was performed. The film formability and skin permeability of the
composition, and lasting of moist skin attained by the composition
were assessed. The results are also shown in Table 18.
TABLE-US-00018 TABLE 18 (Ingredients) (wt. %) Phase A Glyceryl
monobehenate 1.25 I B Cetanol 0.8 B Stearyl alcohol 1.2 C
Pseudo-ceramide*.sup.1 4.0 D 1-(2-Hydroxyethylamino)-3- 0.2
isostearyloxy-2-propanol Hydrogenated lecithin 0.05 B Cholesterol
0.75 Petrolatum 1.75 Dimethylpolysiloxane 3.0 BRS661-C*.sup.2 0.5
Glycerin 15.0 Phase F Water bal. II L-Glutamic acid 0.18
Methylparaben 0.2 Polyethylene glycol 2.0 E Trehalose 5.0 Total 100
((A) + (B))/((A) + (B) + (C)) 0.49 (A)/((A) + (B)) 0.38 (E)/((A) +
(B) + (C)) 0.69 X-ray structure analysis .alpha.-type Film
formability A Permeation sensation 9 Lasting of moist skin 10
*.sup.1N-(hexadecyloxyhydroxypropyl)-N-hydroxyethylhexadecanamide
*.sup.2Bismethoxypropylamideisodocosane
* * * * *