Title of Invention

A HAIR PROTECTING AGENT

Abstract A body surface protecting composition, comprising at least one type of multi- chain multiple hydrophilic group-type compound having two or more hydrophobic groups and two or more hydrophilic groups in the molecule, which has an excellent effect of accelerating the recovery of the barrier function of skin and hair and preventing degradation of that function.
Full Text BODY SURFACE PROTECTING COMPOSITION
TECHNICAL FIELD
[0001] The present invention relates to a composition that is used in applications to
prevent or reduce disorders on a body surface (skin, hair, and the like), specifically
relates to a body surface protecting composition. In particular, the present invention
relates to a body surface protecting composition which has the excellent effects of
accelerating the recovery of the barrier functions of skin and hair, and preventing
degradation of those functions.
BACKGROUND ART
[0002] Skin barrier functions include a function that prevent invasion by foreign
matter from outside the skin into a body, and a function that prevents water content in
the body from escaping to the outside. When the barrier function of the skin is
degraded, rough skin or inflammation of the skin such as rash can result from
external stimulation, and dry chapped skin can result from an increase in the
transpiration of water from the skin, and therefore itchiness and skin trouble can
easily occur. Furthermore, the barrier function of the hair is primarily a function of
preventing water and aqueous components from escaping to the outside. When the
barrier function of the hair is reduced, the tensile strength and viscoelasticity of the
hair will be degraded, the feel on the skin will be poor, hair styling will be difficult, and
not only will this induce a deterioration in appearance such as luster, but will also
cause damage such as split ends and broken hair.
[0003] Conventionally moisturizing agents have been added to cosmetic materials
in order to improve and prevent this type of dry condition in skin and hair. For
example, patent document 1 discloses a cosmetic material for skin that contains a
polyol such as glycerin or ethylene glycol, or urea, hyaluronic acid or an amino acid
or the like as a moisturizing agent. However, with these cosmetic materials, the
effect is temporary and is insufficient for resolving the aforementioned problems.
Furthermore, this cosmetic material is not used for applications to reduce and prevent
damage to the surface of the body, and there is no comment whatsoever concerning
an effect of accelerating improvements in the barrier function of the skin or preventing
a degradation in that function. Furthermore, according to recent dermatological
research, simple application of a moisturizing agent onto the surface of skin will
increase the moisture of the skin for a short period of time, but in actuality may hinder
the intrinsic function of the skin to retain moisture in the skin, and is known to
damage the condition of the skin.
[0004] Furthermore, patent document 2 for instance discloses a composition
comprising an anionic surfactant with two chains and two hydrophilic groups, and
discloses the use as a cosmetic material with moisturizing effects. However, this
composition is also not used for applications to reduce and prevent damage to the
surface of the body, and it dose not disclose any effect of accelerating improvements
in the barrier function of the skin or preventing any degradation in that function, and
does not disclose a compound that has those effects.
[0005] Furthermore, patent document 3 discloses a moisture retaining composition
which does not feel sticky by the combined use of a double chain amide compound
with a polyhydric alcohol. However, this moisture retaining material is essentially a
polyhydric alcohol, and similar to patent document 1, is not used for applications to
reduce and prevent damage to the surface of the body, and it does not disclose any
effect of accelerating improvements in the barrier function of the skin or preventing a
degradation in net function, and only discloses the fact that a double chain amide
compound works to reduce the stickiness when the composition is applied.
[0006] Patent document 4 discloses a composition with low irritability that contains
an anionic surfactant with a double chain bipolar acyl group, but it only disclose the
low irritability of the composition, and dose not disclose any application for preventing
or reducing damage to the surface of the body, nor any effect of proactively
accelerating an improvement of the skin barrier function or preventing a degradation
of that function.
[0007] Patent document 5 discloses an agent to improve skin damage and metabolic
disorders using a Gemini type surfactant, but the Gemini surfactant disclosed in this
document is only a carrier for transporting physiologically active materials through
skin or membrane, and does not show an effect of accelerating an improvement in
the skin barrier function or preventing deterioration of that function.
[0008] On the other hand, a type of sphingolipid such as ceramides obtained either
naturally or synthetically are well-known as substances which improve the skin
barrier function, and for example, patent document 6 discloses a liquid crystal
composition using various types of ceramides, patent document 7 discloses an
external medicine that contains ceramides or substances with a structure similar to a
ceramide, and patent document 8 discloses a skin care agent that contains
ceramides, and discloses a composition that improves skin turn over, improves skin
roughness, and has excellent permeability and moisture retaining properties.
However, all of the ceramides used in these inventions have low water solubility, and
not only cause difficulty when creating a composition, but also require improvisations
in order to permeate into the skin and hair, and cause restrictions on the degree of
freedom of the formulation.
[0009] Therefore there is demand for a raw material which has a strong effect at
accelerating the recovery of the barrier function of skin and hair or in other words the
surface of the body, and has good water solubility.
[0010] On the other hand, in patent document 9, the present inventors have
disclosed a surfactant consisting of a composition containing an acyl group
comprising an N-long chain acyl acidic amino acid derivative made by reacting N-
long chain acyl acidic amino acid anhydride with at least one compound selected
from compounds which have m functional groups of at least one type selected from a
group consisting of a hydroxyl group, an amino group, and a thiol group in the
molecule, as well as a manufacturing method thereof. In this publication, the
surfactant obtained provides surface activity at low concentrations and has been
confirmed to have low irritability.
Patent document 1 Japanese Patent Application Laid-open No.2000-191499
Patent document 2 Japanese Patent Application Laid-open No. H10-218754
Patent document 3 Japanese Patent Application Laid-open No. H10-203956
Patent document 4 Japanese Patent Application Laid-open No. H10-219278
Patent document 5 WO2005/39642
Patent document 6 Japanese Patent Application Laid-open No. H9-124432
Patent document 7 Japanese Patent Application Laid-open No. H5-213731
Patent document 8 Japanese Patent Application Laid-open No. 2001-39859
Patent document 9 Japanese Patent Application Laid-open No. 2002-167313
DISCLOSURE OF INVENTION
PROBLEMS TO BE SOLVED BY THE INVENTION
[0011] An object of the present invention is to provide a body surface protecting
composition which has an excellent effect of accelerating recovery of the barrier
function of skin and hair when that function has deteriorated due to skin trouble or the
like.
[0012] As a result of diligent investigations, the present inventors have discovered
that a multi-chains and multiple hydrophilic group-type compound that has two or
more hydrophobic groups and two or more hydrophilic groups in a molecule has an
excellent effect of improving the barrier function of the skin and hair that is required
because of skin trouble or the like.
[0013] As described above, this multi-chain multiple hydrophilic group-type
compound is known to be a surfactant, but the effect of improving the barrier function
of skin and hair is entirely unknown.
Furthermore, single chain single hydrophilic group-type compounds which have
essentially the same basic constitutional units as multi-chain multiple hydrophilic
group-type compounds can not provide the effect of accelerating recovery of the
barrier function of skin, and conversely cause the barrier function to deteriorate.
Therefore, it was unexpected that multi-chain multiple hydrophilic group-type
compounds have the effect of improving the barrier function of skin and hair.
[0014] Furthermore, the present inventors have discovered that the effect of
improving the barrier function of skin and hair with the present invention is increased
when the multi-chain multiple hydrophilic group-type compound forms a liquid crystal,
and the liquid crystal formation is facilitated by combining a oil-based component with
the multi-chain multiple hydrophilic group-type compound.
[0015] In other words, the present invention is a body surface protecting composition
comprising, (A) at least one type of multi-chain multiple hydrophilic group-type
compound having two or more hydrophobic groups and two or more hydrophilic
groups in the molecule.
[0016] In the multi-chain multiple hydrophilic group compound of (A), it is preferable
that at least one of the hydrophobic groups is an acyl group, and at least one of the
hydrophilic groups is a carboxyl group, sulfonate group, sulfate ester group,
phosphate ester group, or a salt thereof, and it is more preferable that the
aforementioned multi-chain multiple hydrophilic group-type compound further has an
amino acid residue in the molecule.
[0017] Furthermore, a preferred multi-chain multiple hydrophilic group-type
compound of (A) is a compound expressed by the following formula (1).
[0018]
[C1]
Qn-X • • • (1)
[0019] (In formula (1), X represents a spacer with a molecular weight of one million
or less, has m functional group residues that may be the same or different, and may
have other functional groups. Q represents a functional group as expressed by the
following formula (2), the functional groups may be the same or different.
[0020]
[C2]

[0021] In formula (2), Z represents a site of bonding with a functional group residue
contained in X, R1 represents a hydrocarbon group that may be substituted with a
saturated or unsaturated substitution group of from 2 to 20 carbon atoms, R2
represents a hydrogen atom or a lower alkyl group of from 1 to 3 carbon atoms which
may also be substituted with a substitution group, and Y represents a carboxyl group,
a sulfonate group, a sulfate ester group, a phosphate ester group, or a salt thereof, j
and k independently represent either 0, 1, or 2, but j and k cannot both be 0 at the
same time, n is an integer from 2 to 20. Furthermore, m is an integer such that m >
n.).
[0022] In particular, the aforementioned multi-chain multiple hydrophilic group-type
compound of (A) preferably is a compound expressed by the following formula (3).
[0023]
[C3]

[0024] (In formula (3), R11 and R12 each independently represent a hydrocarbon
group which may be substituted with a saturated or unsaturated substitution group of
from 8 to 20 carbon atoms, R21 and R22 each independently represent either a
hydrogen atom or a lower alkyl group of from 1 to 3 carbon atoms that may be
substituted with a substitution group, each Y' independently represents a carboxyl
group or a salt thereof, each W independently represents -0-, -S-, or -NR'- (where
R' represents a hydrogen atom or a hydrocarbon group of from 1 to 10 carbon atoms
which may be substituted with a substitution group), and T represents a spacer of
from 1 to 20 carbon atoms, j1, j2, k1, and k2 independently represent either 0, 1, or 2,
but j1 and k1, and j2 and k2 cannot be both 0 at the same time.).
[0025] Furthermore, the multi-chain multiple hydrophilic group-type compound of (A)
preferably forms a liquid crystal, and therefore the body surface protecting
composition also preferably comprise an oil component (B).
[0026] In the present invention, the multi-chain multiple hydrophilic group-type
compound refers to a compound that has two or more hydrophobic groups and two or
more hydrophilic groups in a molecule, and the hydrophobic groups are not
necessarily restricted to chain compounds.
EFFECT OF THE INVENTION
[0027] The composition of the present invention has an excellent effect of
accelerating recovery of the barrier function of skin and hair when that function has
deteriorated due to skin trouble or the like. Furthermore, the composition of the
present invention also has an excellent effect of restoring damaged tips of hair.
BEST MODE FOR CARRYING OUT THE INVENTION
[0028] The present invention will be described below in detail with a particular focus
on working examples. (A) that is used in the body surface protecting composition of
the present invention is a multi-chain multiple hydrophilic group-type compound
which has two or more hydrophobic groups and two or more hydrophilic groups in a
molecule, and may be any commonly known compound that has this structure.
Furthermore, the two or more hydrophobic groups and hydrophilic groups can be the
same or different.
[0029] The hydrophilic group of the multi-chain multiple hydrophilic group-type
compound of (A) can be a carboxyl group, sulfonate group, sulfate residue,
phosphate residue or a salt thereof, oxyalkylene group, polyethylene glycol group,
amino group, quaternary ammonium group, pyridinium group, sulfonium group, as
well as a salt thereof.
[0030] The hydrophobic group of the multi-chain multiple hydrophilic group-type
compound of (A) can be a saturated or unsaturated straight chain, branched chain, or
cyclical chain group of from 2 to 20 carbon.
[0031] Specific examples of the hydrophobic group of the multi-chain multiple
hydrophilic group-type compound of (A) include n-acetyl, n-propyl, n-butyl, n-pentyl,
n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-
tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and
n-eicosil and the like, as well as branched chain isomers thereof and corresponding
unsaturated residues with 1, 2, or 3 unsaturated-bonds. Of these hydrophobic
groups, long chain hydrocarbon groups of from 8 to 20 carbon atoms are preferable.
[0032] The hydrophobic group of the multi-chain multiple hydrophilic group-type
compound of (A) can be an acyl group derived from a saturated or unsaturated
aliphatic acid. Of these, hydrophobic groups derived from saturated or unsaturated
aliphatic acids of from 2 to 20 carbon atoms are preferable and those of from 8 to 20
carbon atoms are even more preferable.Their form may be straight chain, branched
chain, or cyclic.
[0033] Examples of these acyl groups include acyl groups derived from straight
chain aliphatic acids such as acetic acid, propionic acid, butyric acid, pentanoic acid,
hexanoic acid, hexanoic acid, caprylic acid, pelargonic acid, caprionic acid,
undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid,
palmitic acid, margarinic acid, stearic acid, nonadecanoic acid, and alginic acid;
branched chain aliphatic acids such as 2-butyl-5-methyl pentanoic acid, 2-isobutyl-5-
methyl pentanoic acid, dimethyl octanoic acid, dimethyl nonanoic acid, 2-butyl-5-
methyl hexanoic acid, methyl undecanoic acid, dimethyl decanoic acid, 2-ethyl-3-
methyl nonanoic acid, 2,2-dimethyl-4-ethyl octanoic acid, methyl docosanoic acid, 2-
propyl-3-methyl nonanoic acid, methyl tridecanoic acid, dimethyl dodecanoic acid, 2-
butyl-3-methyl nonanoic acid, methyl tetradecanoic acid, ethyl tridecanoic acid, propyl
dodecanoic acid, butyl undecanoic acid, pentyl decanoic acid, hexyl nonanoic acid,
2-(3-methylbutyl)-3-methyl nonanoic acid, 2-(2-methylbutyl)-3-methyl nonanoic acid,
butylethyl nonanoic acid, methyl pentadecanoic acid, ethyl tetradecanoic acid, propyl
tridecanoic acid, butyl dodecanoic acid, pentyl undecanoic acid, hexyldecanoic acid,
heptylnonanoic acid, dimethyltetradecanoic acid, butylpentyl heptanoic acid, trimethyl
tridecanoic acid, methyl hexadecanoic acid, ethyl pentadecanoic acid, propyl
tetradecanoic acid, butyl tridecanoic acid, pentyl dodecanoic acid, hexyl undecanoic
acid, heptyl decanoic acid, methylheptyl nonanoic acid, dipentyl heptanoic acid,
methyl heptadecanoic acid, ethyl hexadecanoic acid, ethyl hexadecanoic acid, propyl
pentadecanoic acid, butyl tetradecanoic acid, pentyl tridecanoic acid, hexyl
dodecanoic acid, heptyl undecanoic acid, octyl decanoic acid, dimethyl hexadecanoic
acid, methyloctyl nonanoic acid, methyl octadecanoic acid, ethyl heptadecanoic acid,
dimethyl heptadecanoic acid, methyloctyl decanoic acid, methylnon adecanoic acid,
methyl nonadecanoic acid, dimethyl octadecanoic acid, butyl heptylnonanoic acid,
and the like; straight chain monoene acids such as octenoic acid, nonenoic acid,
decenoic acid, caproleic acid, undecylenic acid, lindelic acid, obtusilic acid, laurolenic
acid, tridecenic acid, tsuzuic acid, myristolenic acid, pentadecenic acid, hexadecenic
acid, palmitolenic acid, heptadecenic acid, octadecenic acid, oleic acid, nonadecenic
acid, and gondoic acid; branched monoene acids such as methyl heptenoic, methyl
nonenoic acid, methyl undecenoic acid, dimethyldecenoic acid, methyldodecenoic
acid, methyltridecenoic acid, dimethyldodecenoic acid, dimethyltridecenoic acid,
methyloctadecenoic acid, dimethylheptadecenoic acid, and ethyloctadecenoic acid;
diene or triene acids such as linoleic acid, linoelaidic acid, eleostearic acid, linolenic
acid, linolenelaidic acid, pseudoeleostearic acid, vanillinic acid, and arachidonic acid;
acetylenic acids such as octynoic acid, nonynoic acid, decynoic acid, undecynoic
acid, dodecynoic acid, tridecynoic acid, tetradecynoic acid, pentadecynoic acid,
heptadecynoic acid, octadecynoic acid, nonadecynoic acid, and dimethyl
octadecyne; cyclic acid such as methylene octadecenoic acid, methylene
octdecanoic acid, aleprolic acid, aleprestic acid, aleprylic acid, alepric acid,
hydnocarpic acid, chaulmoogric acid, gorlic acid, a-cyclopentyl acid, a-cyclohexyl
acid, and a-cyclopentylethyl acid.
[0034] An acyl group derived from an aliphatic acid obtained from a natural oil is also
preferably used, and acyl groups derived from mixture of aliphatic acids obtained
from natural oils that include 80% or more of saturated or unsaturated fatty acids of
from 2 to 20 carbon atoms are preferable. Examples of acyl groups derived from
aliphatic acid obtained from natural oils include acyl groups and the like derived from
coconut oil fatty acid, palm oil fatty acid, linseed oil fatty acid, sunflower oil fatty acid,
soybean oil fatty acid, sesame oil fatty acid, castor oil fatty acid, olive oil fatty acid,
camellia oil fatty acid, vegetable oil fatty acids, palm kernel oil fatty acid and the like.
[0035] These acyl groups can be used in combinations of 2 or more.
[0036] When the multi-chain multiple hydrophilic group-type compound of (A) is a
salt, examples can include alkali metal salts, alkali earth metal salts, polyvalent metal
salts, ammonium salts, organic amine salts, and basic amino acid salts and the like.
Specific examples of these salts include one or more types of salt arbitrarily selected
from salt of alkali metals such as sodium, potassium, and lithium, alkali earth metals
such as calcium and magnesium, metals such as aluminum, zinc, iron, cobalt,
titanium, and zirconium, organic amines such as ammonia, monoethanolamine,
diethanolamine, triethanolamine, and triisopropanolamine, and basic amino acids
such as arginine and lysine. Of these salts, sodium salt, potassium salt, organic
amine salt, and basic amino acid salt are particularly preferable.
[0037] In the present invention, at least one type of the multi-chain multiple
hydrophilic group-type compound of (A) is preferably a compound expressed by the
following formula (1).
[0038]
[C4]
Qn-X . . • (1)
[0039] The compound expressed by formula (1) can take a several optical isomer
structure such as a D-isomer, an L-isomer, or a racemic body, and either type can be
used.
[0040] In formula (1), X represents a spacer with a molecular weight of one million or
less, has m functional group residues that may be the same or different, and may
have other functional groups, and the form can be straight chain, branched chain, or
cyclical chain (aromatic hydrocarbon chain). A spacer as used in the present
invention refers to a site that connects a plurality of atom groups in a compound.
[0041] The aforementioned functional group residue can be a residue of a hydroxyl
group, amino group, or a thiol group, or in other words -O-, -S-, or -NR'- (where R'
represents a hydrogen atom or a hydrocarbon group of from 1 to 10 carbon atoms
and which may also be substituted with a substitution group).
[0042] Specific examples of X include amino acids such as serine, threonine,
cysteine, cystine, cystine disulfoxide, cystathionine, methionine, arginine, lysine,
tyrosine, histidine, tryptophan, and oxyproline; compounds with an amino group and
a hydroxyl group in a molecule, such as aminoethanol, aminopropanol, aminobutanol,
aminopentanol, aminohexanol, aminopropanediol, aminoethylethanolamine,
aminoethylaminoethanol, aminoethylaminoethanol, aminocreosol, aminonaphthol,
aminonaphthol sulfonic acid, aminohydroxybenzoic acid, aminohydroxybutanoic acid,
aminophenol, aminophehethyl alcohol, and glucosamine; compounds with a thiol
group and a hydroxyl group in a molecule, such as mercaptoethanol, mercaptophenol,
mercaptopropanediol, and glucothiose; and compounds with a thiol group and an
amino group in a molecule, such as aminothiophenol andaminotriazolethiol. X may
be a protein or a peptide or the like, as well as a residue of a hydrolyzed product
thereof.
[0043] Specific examples of X include dihydroxyl compounds such as ethylene glycol,
1,2-propanediol, 1, 3-propanediol, 1, 2-butanediol, 1,3-butanediol,1,4-butanediol,
pentanediol, 1,6-hexanediol, cyclohexanediol, dimethylol cyclohexane, neopentyl
glycol, 1,8-octanediol, 2,2,4-trimethyl-1,3-pentanediol, isoprene glycol, 3-methyl-1,5-
pentanediol, sorbite, catechol, resorcin, hydroquinone, bis phenol A, bis phenol F,
hydrated bis phenol A, hydrated bis phenol F, dimerdiol, dimethylolpropionic acid,
dimethylolbutanoic acid, tartaric acid, dihydroxytartaric acid, mavalonic acid, 3,4-
dihydroxycinnamic acid, 3, 4-dihydroxyhydrocinnamic acid, hydroxybenzoic acid,
dihydroxystearic acid, dihydroxyphenylalanine, as well as isomers thereof;
trihydric polyhydroxyl compounds such as glycerin, trioxyisobutane, 1,2,3-butanetriol,
1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-
1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol,
2,4-dimethyl-2,3,4-pentanetriol, 1,2,4-butanetriol, 1,2,4-pentanetriol,
trimethylolethane, trimethylolpropane, diethanolamine, triethanolamine, and
trihydroxystearic acid; quadrahydric polyhydroxyl compounds such as pentaerythritol,
erythritol, 1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol, 1,2,4,5-pentanetetrol, 1,3,4,5-
hexanetetrol, diglycerin, and sorbitan; pentahydric poly hydroxyl compounds such as
adonitol, arabitol, xylytol, and triglycerin; hexahydric polyhydroxyl compounds such
as dipentaerythritol, sorbitol, mannitol, iditol, inositol, dulcitol, talose, and allose;as
well as condensate products thereof, and polyglycerin and the like.
[0044] Examples of sugars include residues of polyhydroxyl compounds such as
monosaccharides such as tetroses such as erythrose, threose, and erythrulose;
pentoses such as ribose, arabinose, xylose, licsose, xylulose, and rubulose; and
hexoses such as allose, artrose, glucose, mannose, gulose, idose, galactose, talose,
fructose, sorbose, psicose, and tagatose; and oligosaccharides such as maltose,
isomaltose, cellobiose, genthiobiose, melibiose, lactose, turanose, trehalose,
saccharose, mannitolylose, cellotriose, genthianose, raffinose, melezitose,
cellotetrose, and stachyose, and the like.
[0045] X may also be residues of other sugars such as heptose, deoxy sugar, amino
sugar, thio sugar, sereno sugar, aldonic acid, uronic acid, saccharic acid, ketoaldonic
acid, anhydro sugar, unsaturated sugar, sugar ester, sugar ether, and glycoside, as
well as polysaccharides such as starch, glycogen, cellulose, chitin, and chitosan, as
well as hydrolyzed residues thereof.
[0046] Specific examples of X also includes residues of polyamino compounds such
as aliphatic diamines such as N,N'-dimethylhydrazine, ethylenediamine, N,N'-
dimethylethylenediamine, diaminopropane, diaminobutane, diaminopentane,
diaminohexane, diaminoheptane, diaminooctane, diaminononane, diaminodecane,
diaminododecane, diaminoadipic acid, diaminopropanoic acid, diaminobutanoic acid
and various isomers thereof; aliphatic triamines such as diethylenetriamine,
triaminohexane, triaminododecane, 1,8-diamino-4-aminomethyl-octane, 2,6-
diaminocapric acid-2-aminoethyl ester, 1,3,6-triaminohexane, 1,6,11-triamino
undecane, di(aminoethyl) amine, as well as various isomers thereof; alicyclic
polyamines such as diaminocyclobutane, diaminocyclohexane, 3-aminomethyl-3,5,5-
trimethylcyclohexylamine, and triaminocyclohexane; aromatic polyamines such as
diaminobenzene, diaminotoluene, diaminobenzoic acid, diaminoanthraquinone,
diaminobenzenesulfonic acid, diaminobenzoic acid, and various isomers thereof;
araliphatic polyamine such as diaminoxylene, di(aminomethyl)benzene,
di(aminomethyl)pyridine, di(aminomethyl)naphthalene, and various isomers thereof;
hydroxyl group substituted polyamines such as diaminohydroxypropane and various
isomers thereof, and the like.
[0047] Furthermore, specific examples of X also include residues of dithiol
compounds such as dithioethylene glycol, dithioerythritol, and dithiothreitol.
[0048] X preferably has from 1 to carbons, more preferably from 1 to 20 carbons.
Furthermore, X is preferably in a naturally existing form, because the biodegradability
will be excellent.
[0049] When X is an amino acid residue, the affinity of the compound expressed in
formula (1) towards skin and hair will be high, and the compound expressed in
formula (1) will easily permeate into skin and hair so the effect of improving the
barrier function will be further accelerated.
[0050] In formula (1), Q is a substitution group expressed in formula (2), and each
functional groups may be the same or different.
[0051]
• [C5]

[0052] In formula (2), R1 represents a hydrocarbon group that may be substituted
with a saturated or unsaturated substitution group of from 2 to 20 carbon atoms, and
may be a straight chain, branched chain, or ring. A saturated or unsaturated
hydrocarbon group of from 8 to 20 carbon atoms is preferable.
[0053] In formula (2), R2 represents a hydrogen atom or a lower alkyl group of from 1
to 3 carbon atoms such as a carboxyl group, a sulfonate group, a sulfate ester group,
a phosphate ester group, or salts thereof, and may also be substituted. Examples
include a methyl group, an ethyl group, a propyl group, an isopropyl group, a
hydroxymethyl group, a hydroxyethyl group, a hydroxy(iso)propyl group, a
dihydroxy(iso)propyl group, a carboxymethyl group, a carboxyethyl group, a
carboxypropyl group, and a sulfoethyl group.
[0054] In formula (2), Y represents a carboxyl group, a sulfonate group, a sulfate
ester group, a phosphate ester group, or a salt thereof. Salts of carboxyl groups,
sulfonate groups, sulfate ester groups, and phosphate ester groups include alkali
metal salts, alkali earth salts, polyvalent metal salts, ammonium salts, organic amine
salts, and basic amino acid salts, and specific examples include alkali metals such as
sodium, potassium, and lithium; alkali earth metals such as calcium and magnesium;
metals such as aluminum, zinc, iron, cobalt, titanium, and zirconium; organic amines
such as ammonia, monoethanolamine, diethanolamine, triethanolamine, and
triisopropanolamine, and basic amino acids such as arginine and lysine.
[0055] In formula (2), Z is a site of a bonding with a functional group residue
contained in X.
[0056] A preferred substitution group Q expressed in formula (2) is a residue of an
N-acylated acidic amino acid because the effect of improving the barrier function of
the skin and hair will be further enhanced. Acidic amino acid as used in the present
invention refers to a monoaminodicarboxylic acid having 2 carboxyl groups and 1
amino group present in a molecule, and the amino group may be an N-methyl group
or an N-ethyl group. The substitution group Q expressed in formula (2) can be any
optical isomers of a D-isomer, L-isomer or racemic body, but Q is preferably a
residue of an L-acidic amino acid compound because the biodegradability will be
excellent.
[0057] Examples of acidic amino acids include glutamic acid, asparatic acid,
lanthionine, ß-methyllanthionine, cystathionine, diencolic acid, felinine, aminomalonic
acid, ß-oxyasparginic acid, a-amino-a-methylsuccinic acid, ß-oxyglutamic acid, ?-
oxyglutamic acid, ?-methylglutamic acid ?-methyleneglutamic acid, ?-methyl-?-
oxyglutamic acid, a-aminoadipic acid, a-amino-?-oxyadipic acid, a-aminopimelic acid,
a-amino-?-oxypimelic acid, ß-aminopimelic acid, a-aminosuberic acid, a-
aminosebacic acid, and pantotenic acid.
[0058] The top layer of human skin and hair is a layer known as the horny layer, and
this horny layer consits of cells that have been keratinized (keratinized cells), and
"intercellular lipids" that fill in the gaps of the cells. The barrier function of the skin is
thought to be primarily dependent on the "intercellular lipids", and these "intercellular
lipids" are primarily made of ceramides, and align in plane to adopt a "lamellar
structure" that retains moisture between the structural elements. Degradation of the
barrier function of skin and hair is thought to be caused by a loss of ceramides from
the horny layer for some reason, and by disorganizing of the lamellar structure of the
intercellular lipids.
[0059] It is hypothesized that the multi-chain multiple hydrophilic group-type
compound expressed by formula (1) can easily align in a plane because of the bulk
balance and positional relationship of the hydrophobic and hydrophilic groups, and
when the multi-chain multiple hydrophilic group-type compound permeates into the
horny layer of skin where the intracellular lipid lamellar structure has become
disorganized, the compound can easily create the lamellar structure together with the
remaining ceramide. Furthermore, the surface activity and the permeability are high,
so the compound easily penetrates into the horny layer when applied to the surface
of the skin. Therefore, it is thought that when the multi-chain multiple hydrophilic
group-type compound expressed by formula (1) is applied to the surface of the skin,
the compound permeates into the horny layer, acts in a manner similar to ceramide
replacing the ceramide that was lost, and restores the barrier function of the skin.
[0060] The compound expressed by formula (1) is preferably the compound
expressed by the following formula (3).
[0061]
[C6]

[0062] (In formula (3), R11 and R12 each independently represent a hydrocarbon
group which may be substituted with a saturated or unsaturated substitution group of
from 8 to 20 carbon atoms, R21 and R22 each independently represent either a
hydrogen atom or a lower alkyl group of from 1 to 3 carbon atoms that may be
substituted with a substitution group, each Y' independently represents a carboxyl
group or a salt thereof, each W independently represents -O-, -S-, or -NR- (where
R' represents a hydrogen atom or a hydrocarbon group of from 1 to 10 carbon atoms
which may be substituted with a substitution group), and T represents a spacer of
from 1 to 20 carbon atoms, j1, j2, k1, and k2 independently represent either 0, 1, or 2,
but j1 and k1, and j2 and k2 cannot both be 0 at the same time.)
[0063] In this case, (A) have three carboxyl groups or salts thereof as hydrophilic
groups, and this is preferable because the solubility will be improved and the
permeability towards skin and hair will be enhanced as compared to a conventionally
known double chain double hydrophilic group-type amphipathic substance or the
compound where X has a hydroxyl group as a hydrophilic group.
[0064] Specific examples of compounds expressed by formula (1) are shown below.
[0065]
[C7]
[0077] The compound expressed by formula (1) can be prepared by reacting N-acyl
acidic amino acid anhydride expressed by formula (4) with a polyhydroxyl compound,
polyamino compound, polythiol compound, or a compound which has m functional
groups and such as a hydroxyl group, amino group, or thiol group or the like in a
molecule, either in water, solvent blends with an organic solvent and water, or an
inert solvent such as tetrahydrofuran, benzene, toluene, xylene, carbon tetrachloride,
chloroform, and acetone, or without a solvent, at a temperature that is from -5°C to
200°C but in any case, above the melting point.
[0078]
[C19]

[0079] The compound expressed by formula (1) can be prepared for example by
dissolving N-acyl acidic amino acid mono lower ester or the like (such as methyl ester
or an ethyl ester) and a polyhydroxyl compound, polyamino compound polythiol
compound, or a compound having m functional groups such as hydroxyl group,
amino group, or thiol group or the like in a molecule, in an appropriate solvent such
as dimethylformamide, adding a catalyst such as potassium carbonate, and reacting
while heating under reduced pressure at a temperature of -5°C - 250°C, followed by
removing the reaction solvent; or by heating and melting them without a solvent,
adding a catalyst such as sodium hydroxide and performing an ester replacement
reaction at a temperature of room temperature to 250°C.
[0080] The formulation ratio of the body surface protecting composition of the
present invention is not particularly restricted, but the amount of multi-chain multiple
hydrophilic group-type compound of (A) is preferably from 0.001 to 20 mass%, more
preferably from 0.01 to 10 mass%, and yet more preferably from 0.01 to 5 mass%. If
the amount of multi-chain multiple hydrophilic group-type compound is below the
aforementioned range, the effect of improving or preventing a degradation in the
barrier function of the skin may not be sufficient.
[0081] The oil-based component of (B) that is added in a embodiment of the body
surface protecting composition of the present invention can be a volatile or non-
volatile oil, including natural ceramide such as ceramide 1, ceramide 2, ceramide 3,
ceramide 4, ceramide 5, ceramide 6, ceramide 7, phytoceramide, N-oleoyl
sphingosine, N-(12-hydroxyoctadecanoyl) sphingosine, N-(16-hydroxyhexadecanoyl)
sphingosine, glycosphingolipid, (N-acyl) phytosphingosine, and animal brain extract;
synthetic ceramides such as photoactive ceramide 2 and photoactive ceramide 3;
pseudocermides such as O-acyl ceramide, stearoyl dihydrosphingosine, stearoyl
phytosphingosine; higher fatty acids such as lower acid, myristic acid, palmitic acid,
stearic acid, isostearic acid, oleic acid, behenic acid, undecilenic acid, lanolin fatty
acid, hardened lanolin fatty acid, soft lanolin fatty acid, linoleic acid, linolenic acid
eicosapentaenoic acid, and 12-hydroxystearic acid; cholesterol esters such as
cholesterol palmitate, cholesterol isostearate, di(cholesterol, 2-octyldodecyl)
acylglutamate, cholesterol lanolate, and cholesterol hydroxystearate; animal or plant
sterols such as cholesterol and phytosterol as well as derivatives thereof;
phosphosphingolipid such as sphingomyelin; phospholipids such as lecithin
derivatives; fats and oils such as avocado oil, turtle oil, corn oil, almond oil, olive oil,
cacao oil, sesame oil, safflower oil, soybean oil, camellia oil, apricot oil, castor oil,
grape seed oil, macadamia nut oil, mink oil, cottonsed oil, Japan wax, coconut oil,
egg yolk oil, palm oil, palm kernel oil, triisooctanoic acid glycerin, tri-2-ethylhexanoic
acid glyceryl cholesterol fatty acid ester, wheat germ oil, camellia kissi seed oil,
linseed oil, Oenothera tetraptera oil, perilla oil, peanut oil, tea seed oil, kaya oil, rice
bran oil, cinnamon bark oil, Japan tung oil, jojoba oil, germ oil, glycerin trioctanoate,
glycerin triisopalmitate, horse oil, hardened coconut oil, beef tallow, hoof oil, sheep
tallow, hardened beef tallow, pork tallow, beef bone oil, Japan wax kernel oil,
hardened oil, Japan wax, and hardened castor oil; hydrocarbons such as liquid
paraffin, vaseline, ceresin, microcrystalline wax, isoparaffin, ozokerite, squalene,
pristane, and squalane; waxes such as yellow beeswax, whale oil, lanolin, carnauba
wax, candelilla wax, cotton wax, bayberry wax, privet wax, montan wax, bran wax,
lanolin, kapok wax, lanolin acetate, liquid paraffin, sugar cane wax, isopropyl lanolate,
hexyl laurate, reduced lanolin, jojoba wax, hardened lanolin, shellac wax,
polyoxyethylene lanolin alcohol ether, polyoxyethylene lanolin alcohol acetate,
polyethylene glycol lanolate, polyoxyethylene hydrogenated lanolin alcohol ether and
derivatives thereof; higher alcohols such as lauryl alcohol, cetanol, cetostearyl
alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, lanolin alcohol, hydrogenated
lanolin alcohol, hexyldecanol, and octyldodecanol; ester oils such as isopropyl
myristate, butyl stearate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate,
hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, cetyl
lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate,
cholesterol 12-hydroxystearate, ethylene glycol di-2-ethylhexanoate, dipentaerythritol
fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol dicapric acid,
diisosterile malate, glycerin di-2-heptylundecanoate, trimethylolpropane tri-2-
ethylhexanoate, trimethylolpropane triisostearate, pentaerythritol tetra-2-
ethylhexanoate, glycerin tri-2-ethylhexanoate, trimethylolpropane triisostearate, cetyl-
2-ethyl hexanoate, 2-ethylhexyl palmitate, glycerin trimyristate, glyceride tri-2-
heptylundecanoate, methyl castor oil fatty acid ester, oleoyl oleate, cetostearyl
alcohol, acetoglyceride, 2-heptylundecyl palmitate, diisopropyl adipate, N-lauroyl-L-
glutamic acid -2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-2-
ethylhexyl sebacate, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl
adipate, diisopropyl sebacate, 2-ethylhexyl succinate, ethyl acetate, butyl acetate,
amyl acetate, and triethyl citrate; and silicones such as metal soap, dimethyl
polysiloxane, polyether modified silicone, alcohol modified silicone, methylphenyl
polysiloxane, epoxy modified silicone, fluorine modified silicone, alkyl modified
silicone, alkyloxy modified silicone, amino modified silicone, and volatile silicone.
[0082] These substances can be used independently, or in combination of two or
more. When two or more types are used in combination, a premix of materials
blended beforehand can be used.
[0083] (B) is preferably a material (liquid crystal formation aid) that has excellent
performance in accelerating the liquid crystal formation of (A).
[0084] Oil components which have an excellent performance at accelerating the
liquid crystal formation of (A) include natural, synthetic, or pseudo- ceramides,
cholesterol esters, sterols and derivatives thereof, sphingophospholipids,
phospholipids, higher fatty acids, and higher alcohols.
[0085] Specific examples include cholesterol esters such as cholesterol palmitate,
cholesterol isostearate, di(cholesterol, 2-octyldodecyl) acylglutamate, cholesterol
lanolate, and cholesterol hydroxystearate; animal or plant sterols such as cholesterol
and phytosterol as well as derivatives thereof; higher fatty acids such as lower acid,
myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, behenic acid,
undecilenic acid, lanolin fatty acid, hardened lanolin fatty acid, soft lanolin fatty acid,
linoleic acid, linolenic acid eicosapentaenoic acid, and 12-hydroxystearic acid.
[0086] Of these, at least one type of sterol compound selected from cholesterol,
cytosterol, lanosterol, phytosterol, dihydrocholesterol, dihydrolanosterol,
dehydrosterol and esters thereof and a higher fatty acid or a salt thereof having from
6 to 22 carbon atoms are preferable.
[0087] Of these, cholesterol, cytosterol, lanosterol, phytosterol, dihydrocholesterol,
dihydrolanosterol, dehydrochloresterol and esters thereof are particularly preferable.
[0088] The amount of (B) added can be set within a range that does not hinder the
effect of the present invention, and from the viewpoint of the effect of accelerating the
liquid crystal formation of (A), the molar ratio with regards to component (A) (amount
of (B): amount of (A)) is preferably 1:10 or higher and 10:1 or lower, and more
preferably the molar ratio with regards to (A) is 1:5 or higher and 5:1 or lower.
[0089] The homy layer intercellular component of (C) added to the example of the
body surface protecting composition of the present invention is a water-soluble
component other than (B) that exists in the horny layer intercellular space, and
examples include NMF (natural moisturizing factors) such as amino acids, lactic acid,
urea, and citrates.
[0090] The water-soluble moisturizing agent (D) added to the preferable embodiment
of the body surface protecting composition of the present invention is a water-soluble
component that has moisture retaining capability other than (C) and that essentially
does not exist naturally in the horny layer intercellular space, and examples include:
polyols such as glycerin, diglycerin, polyglycerin, 1,3-butanediol, propanediol, and
polyethylene glycol; alkyl glycines such as N-methylglycine, N,N- dimethylglycine,
N,N,N-trimethylglycine, and N-ethylglycine; (poly) saccharides and derivatives thereof
such as sorbitol, raffinose, pyrrolidone carboxylates, lactate, hyaluronates, ceramides,
trehalose, xylobiose, maltose, sucrose, glucose, and vegetable viscosity modifying
polysaccharides; and water-soluble moisture retaining substances such as water-
soluble chitin, chitosan, pectin, chondroitin sulfate, and other glycosamino glycanes
and salts thereof, glycine, serine, theonine, alanine, asparatic acid, thyrosine, valine,
luecine, alginine, glutamine, prolinic acid and other amino acides and salts thereof,
aminocarbonyl reaction products and other saccharide amino acid compounds, aloe,
horse chestnut and other vegetable extracts solutions, urea, uric acid, ammonia,
glucosamine, creatine, DNA, RNA, and other nucleic acid related substances.
[0091] These substances can be used independently, or in combination of two or
more. If two or more types are used in combination, a premix of materials blended
beforehand can be used.
[0092] The body surface protecting composition of the present invention can be in a
variety of forms depending on the objective, including liquid, solid, gel, paste, cream,
slurry, emulsion, suspension, mist, liquid crystal, powder, or aerosol or the like.
However, the forms are not limited to these examples.
[0093] The body surface protecting composition of the present invention can be
unneutralized or neutralized using a basic substance, depending on the application
and objective.
The multi-chain multiple hydrophilic group-type compound will have enhanced water
solubility if neutralized by a basic substance, so when the body surface protecting
composition of the present invention is a water based composition, neutralizing is
preferable for the sake of handling.
In this case, the pH of the water based composition is preferably adjusted to from 3 to
12 by adjusting the degree of a neutralization using the basic substance, but a pH
from 4.5 to 11 is more preferable, and a pH from 5 to 8 is still more preferable.
[0094] The body surface protecting composition of the present invention can be used
as an agent to protect the surface of the body, or can be broadly used as a
composition that contact with humans such as cosmetics and toiletries or medicines.
[0095] In the present invention, a body surface protecting agent refers to a
substance that is applied externally to the surface of the body (skin, hair, or the like)
and prevents or reduces damage to the surface of the body.
[0096] In the present invention, the term cosmetics and toiletries refers to quasi drug
and cosmetic products as defined in the Japanese Pharmaceutical Affairs Law, and
specific examples include quasi drug such as mouthwash, underarm deodorant, bath
dusting powder, hair growth stimulants, hair removal products, hair dyes, permanent
wave solutions, bathing salts, medicinal cosmetics, and medicated toothpaste; and
cosmetics, such as cleaning cosmetics such as cosmetic soaps, facial washes (as
cream, paste, liquid, gel, granule, outer, or aerosol, or the like), shampoo, and rinse;
scalp and hair cosmetics such as hair dyes, hair treatments (as a cream, mist, oil, gel,
or other form and also including split end coating agents), and hair setting agents
(hair grease, setting lotion, curling lotion, pomade, stick, fragrant hair oil, hairspray,
hair mist, hair liquid, hair foam, hair gel, and water grease); basic cosmetics, such as
general creams, emulsions (cleansing cream, cold cream, vanishing cream, and
cream, and the like), shaving cream (after shave cream, shaving cream, and the like),
skin lotion (hand lotion, general cosmetic lotion, and the like), cologne, shaving lotion
(after shaving lotion, shaving lotion and the like), cosmetic oils, and packs; makeup
cosmetics such as skin whiteners (whitening cream, whitening solids, whitening
powder, talcum powder, whitening paste, baby powder, body powder, whitening
water, and the like), powder, foundation (as cream, liquid, or solid, or the like), rouge,
eyebrow pencil, eye cream, eye shadow, and mascara; perfumes such as standard
perfume, paste perfume, and powder perfume; gel, liquid, or ceramic type fragrances,
air fresheners, and deodorizers; suntan and sunblock cosmetics such as suntan or
sunblock creams, suntan or sunblock lotions, and suntan or sunblock oils; nail
cosmetics such as nail creams, fingernail polish, and fingernail polish remover;
eyeliner cosmetics; mouth and lip cosmetics such as lipstick and lip creams; oral
cosmetics such as toothpaste; and bath cosmetics such as bath salt, bath oil, and
bubble bath.
[0097] Various types of materials that are normally used in external preparations
such as cosmetics and toiletries or medicinal products can be added to the body
surface protecting composition of the present invention based on the application and
objectives, to the degree that the object of the present invention is not hindered.
[0098] Specific examples include dispersing agents such as natural gums like arabia
gum and tragacanth gum, glucosides such as saponin, cellulose derivatives such as
methylcellulose, carboxycellulose, and hydroxymethylcellulose, natural polymers
such as lignin solfonate and shellac, anionic polymers such as polyacrylate, styrene-
acrylic acid copolymer salts, vinyl naphthalene-maleic acid copolymer salts, sodium
salts of B-naphthalene sulfonate formalin condensates, and phosphates, and
nonionic polymers such as polyvinyl alcohol, polyvinylpyrrolidone, and polyethylene
glycol; high level fatty acid salt (soap); high-level fatty acids salts with a hydrophobic
group containing between 8 and 20 carbons; N-acylamino acid based anionic
surfactants (where the acyl group has between 8 and 20 carbons as described above,
and the component amino acid is an amino acid such as the aforementioned acidic
amino acids like glutamic acid and aspartic acid, as well as glycine, alanine, valine,
leucine, isoleucine, proline, methionine, cystine, tryptophan, tyrosine, phenylalanine,
asparagine, glutamine, serine, threonine, oxyproline, 3-aminopropionic acid, ?-
aminobutanoic acid, anthranilic acid, m-aminobenzoic acid, and ß-aminobenzoic
acid); anionic surfactants such as alkyl ether carboxylates, amide ether carboxylates,
alkyl sulfate ester (AS), polyoxyethylene alkyl ether sulfate esters (AES), alkyl ether
sulfate, sulfates of high-level fatty acid esters, sulfates of high-level fatty acid
alkylolamides, sulfated oils, polyoxyethylenated phenyl ether sulfates, a-olefin
sulfonates (AOS), alkylbenzene sulfonates, alkylnaphthalene sulfonates, alkyl
sulfonates (SAS), dialkylsulfosuccinate, a-sulfonated fatty acid salts, alkane
sulfonates, sulfonates of higher-level fatty acid esters, a-sulfonated fatty acid salts,
sulfonates of higher-level fatty acid amides, N-acyl-N-alkyltaurate, N-acyl-N-
methyltaurate, alkyl phosphates, alkyl ether phosphates, polyoxyethylene alkyl ether
phosphates, polyoxyethylene alkylphenyl ether phosphates, and
naphthalenesulfonate formalin condensate; amphoteric surfactants such as
alkylbetaines, alkylamidebetaines, alkylsulfobetaines, imidazolinium betaines, and
lecithins; oxygenated ethylene condensate type nonionic surfactants such as
polyoxyethylene alkyl ether (AE), polyoxyethylene alkylphenyl ether, polyoxyethylene
polystearylphenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene
polyoxypropylene alkyl ether, polyoxyalkylene fatty acid ester, polyoxyalkylene
sorbitan fatty acid ester, polyoxyalkylene fatty acid alkanolamide, polyoxyalkylene
alkyl glycoside, polyoxyalkylene harden castor oil, polyoxyalkylene alkylamine, and
polyoxyalkylene alkylphenyl ether; polyhydric alcohol ester type nonionic surfactants
such as polyhydric alcohol fatty acid part ester, polyoxyethylene polyhydric alcohol
fatty acid part ester, polyoxyethylene fatty acid ester, (poly)glycerin fatty acid ester,
polyoxyethylene hardened castor oil, polyoxyethylene alkylamine, triethanolamine
fatty acid part ester, alkyl polyglycoside, propylene glycol fatty acid ester, sorbitan
fatty acid ester, and sucrose or the like fatty acid esters; nonionic surfactants such as
fatty acid alkanolamide, sugar amine acyl compounds, triethanolamine fatty acid part
ester, fatty acid alkylolamide, and alkylamine oxide; cationic surfactants such as
primary through tertiary fatty acid amine salts, alkylammonium chloride, tetraalkyl
ammonium salt, trialkylbenzyl ammonium salt, alkylpyridinium salt, alkylhydroxylethyl
imidazolinium salt, dialkylmorpholinium salt, alkylisoquinolium salt, benzetonium salt,
and benzalkonium salt; polymer surfactants such as sodium alginate, starch
derivatives, and tragacanth gum; natural surfactants such as phospholipids, lecithin,
lanolin, cholesterol, and saponin; oil soluble polymers such as hydroxyethyl cellulose,
carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyltrimethyl ammonium
chloride ether, methylcellulose, ethyl cellulose, hydroxypropyl cellulose,
methyl hydroxy propyl cellulose, soluble starch, carboxymethyl starch, methyl starch,
propylene glycol alginate ester, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl
methyl ether, carboxyvinyl polymer, polyacrylate, guar gum, locust bean gum,
queenseed, carrageenan, galactan, arabia gum, pectin, mannan, starch, xanthum
gum, dextran, succinoglucane, cardlan, hyaluronic acid, gelatin, casein, albumin,
collagen, methoxyethylene maleic anhydride copolymer, amphoteric methacrylate
ester copolymer, polydimethylmethylene piperidinium chloride, polyacrylate ester
copolymer, polyvinyl acetate, nitrocellulose, and silicone resin; cationic polymers
such as cationized cellulose derivative, cationic starch, cationized guar gum
derivative, diallylquaternary ammonium salt/acrylamide copolymer, quaternized
polyvinyl pyrrolidone derivative, quaternized vinyl pyrrolidone/vinyl imidazole polymer,
polyglycol/amine condensate, quaternized collagen polypeptide, polyethyleneimine,
cationic silicone polymer, adipic acid/dimethylamino hydroxypropyl diethylene
triamine copolymer, polyaminopolyamide, cationic chitin derivative, and quaternized
polymer; thickeners and foaming components such as polyethylene glycol fatty acid
ester, polyoxyethylene fatty acid ester methylglycoside, and tetradecene sulfonates;
sequestering agents such as ethylenediamine tetraacetate and salts thereof,
hydroxyethylenediamine triacetate and salts thereof, phosphoric acid, ascorbic acid,
succinic acid, gluconic acid, poly phosphates, methaphosphates, and hinokithil
(Japanese cypress extract); preservatives and antimicrobial agents such as
paraoxybenzoate esters, benzoic acid and salts thereof, phenoxyethanol, hinokithil
(Japanese cypress extract), salicylic acid and salts thereof, sorbic acid and salts-
thereof, dehydroacetic acid and salts thereof, parachloromethacresol,
hexachlorophene, boric acid, resorcin, tribromsalan, ortho-phenyl phenol, thiram,
photosensitizing dye 201, halocarbane, trichlorocarbanide, tocopherol acetate, zinc
pyrithione, phenol, isopropylmethylphenol, 2,4,4-trichloro-2-hydroxyphenol,
hexachlorophene, chlorohexedine, benzetonium chloride, benzalkonium chloride,
cetylpyridinium chloride, decalinium chloride, stearyldimethyl ammonium chloride,
stearyltrimethyl ammonium chloride, cetyltrimethyl ammonium chloride,
methylbenzetonium chloride, lauryltrimethyl ammonium chloride, lauroyl colamino
formylmethyl pyridinium chloride, trichlosan, and biozole; pH adjusting agents such
as citric acid, malic acid, adipic acid, glutamic acid, and asparaginic acid; as well as
other dandruff and itch preventing agents such as trichlorocarbanilide, salicylic acid,
zinc pyrithione, and isopropylmethyl phenol; ultraviolet light absorbers such as
benzophenone derivatives, paraminobenzoic acid derivatives, paramethoxycinnamic
acid derivatives, and salicylic acid derivatives; whitening agents such as ascorbic
acid and salts thereof (alkali metal salts and alkali earth metal salts such as sodium
salt, potassium salt, magnesium salts, and calcium salts, as well as ammonium salts
and amino acid salts, and the like), ascorbic acid derivatives (alkyl L-ascorbate ester,
L-ascorbic acid phosphate ester and salts thereof, L-ascorbic acid-2-sulfate ester and
salts thereof, and L-ascorbic acid glucoside and the like), alkoxysalicylic acid and
salts thereof (examples of the alkoxy groups include methoxy groups, ethoxy groups,
propoxy groups, an isopropoxy groups, butoxy groups, and isobutoxy groups, and
the like), hydroquinone glycoside and derivatives thereof (albutin and the like), kojic
acid and derivatives thereof, ellagic acid, camomile extract, althaea extract, liver
extract, mulberry bark extract, raspberry extract, apple flavonoid, bran extract,
vitamin E and derivatives thereof, hinokithiol, placenta extract, leucinol, camomilla ET,
glutathione, clove extract, tea extract, astaxanthin, bovine placenta extract,
tranexamic acid and derivatives thereof, resorts and derivatives thereof, azulene, and
?-hydroxybutanoic acid; blood circulation enhancers such as swertia extract,
cepharanthin, vitamin E and derivatives thereof, and ?-oryzanol; local stimulants such
as capsicum tincture, ginger tincture, cantharide tincture, and benzyl nicotinate ester;
nutrients such as various vitamins and amino acids; female hormones; hair root
activator; antiinflammatories such as glycyrrhetic acid, glycyrrhizinic acid derivative,
allantoin, azulene, aminocaproic acid, and hydrocortizone; astringents such as zinc
oxide, zinc sulfate, allantoin hydroxy aluminum, aluminum chloride, zinc
sulfocarbolate, tannic acid, citric acid, and lactic acid; cooling agents such as menthol
and camphor; antihistamines such as diphenhydramine hydrochloride,
chlorpheniramine maleate, and glycyrrhizinic acid derivatives; silicone based
substances such as polymer silicone and cyclic silicone; antioxidants such as
tocopherols, BHA, BHT, gallic acid, and NDGA; sebum inhibitors such as estradiol,
estrone, and ethinylestradiol; keratin peelers and dissolvers such as sulfur, salicylic
acid, and resorcin; a-hydroxyacids such as glycolic acid, lactic acid, malic acid,
tartaric acid, and citric acid; cosmetic colorants such as talc, kaolin, sericite, calcium
carbonate, zinc oxide, aluminum oxide, magnesium oxide, zirconium oxide,
magnesium carbonate, calcium carbonate, barium carbonate, chromium oxide,
chromium hydroxide, tar based colorants, mica, (synthetic) sericite, silicon carbide,
boron nitride, titanium dioxide, black titanium oxide, navy blue, red iron oxide, black
iron oxide, yellow iron oxide, ultramarine, titanium coated mica, bismuth oxychloride,
bengara, body pigments, ultramarine pink, ultramarine violet, chromium hydroxide,
mica titanium, chromium oxide, aluminum cobalt oxide, carbon black, silicic
anhydride, magnesium silicate, bentonite, (synthetic) mica, zirconium oxide, (meta)
magnesium aluminosilicate, calcium aluminosilicate, polyethylene powder, nylon
powder, polymethylmethacrylate, polyethylene terephthalate-polymethyl methacrylate
layered powder, acrylonitrile-methacrylic acid copolymer powder, vinylidene chloride-
methacrylic acid copolymer powder, wool powder, silk powder, crystalline cellulose,
N-acyllysine, polymethylsilsesquioxane powder, plant fruit or peel powders, bismuth
oxychloride, mica titanium, iron oxide coated mica, iron oxide mica titanium, organic
pigment treated mica titanium, aluminum powder, fine powdered titanium oxide, fine
powdered zinc oxide, fine powdered titanium oxide coated mica titanium, fine
powdered zinc oxide coated mica titanium, barium sulfate coated mica titanium,
carmine, 3-carotene, chlorophyll, sunset yellow FCF, ponceau SX, eosine YS,
tetrabromofluorescein, rhodamine B, quinoline yellow SS, quinoline yellow WS,
alizanine cyanine green, quinizarin green, resolvin B, resolvin BCA, parmatone red,
helindon pink CN, phthalocyanine blue, (3-apo-8-carotinal, capsanthin, rilopine, bixin,
crocin, canthaxanthin, shisonin, lafanine, ninocyanine, carsamine, safrole yellow,
rutine, quercitine, cocoa colorant, riboflavin, laccaic acid, carminic acid, kermesic acid,
alizanine, shikonin, alkannin, nikino chrome, hemaglobin, curcumin, and betanin; as
well as purified water, pyracantha extract, n-methyl-l-serine, whey, nicotinamide,
diisopropylamine dichloroacetate, mevalonic acid, ?-aminobutanoic acid (including ?-
amino-ß-hydroxybutanoic acid), althaea extract, aloe extract, apricot kernel extract,
turmeric extract, oolong tea extract, dried seawater, hydrolyzed wheat powder,
hydrolyzed ,silk, carrot extract, cucumber extract, gentian extract, yeast extract, rice
germ extract, comfrey extract, caryophyllaceae extract, rehmannia root extract,
lithospermum root extract, white birch extract, peppermint extract, swertia extract,
bisabolol, propolis, luffa cylindrica extract, tilia platyphyllos flower extract, hop extract,
horse chestnut extract, sapindus mukurossi peel extract, balm mint leaf extract,
eucalyptus leaf extract, saxifraga sarementosa extract, rosemary extract, matricaria
chamomilla extract, royal jelly extract, seaweed, rice bran, liver, citrus unshiu peel,
angelica acutiloba, crushed peach bell, sphingolipids, guaiazulene, and vitamin c and
the like.
[0099] Of the aforementioned materials, fatty acid diethanaolamide, polyoxyethylene
dioleic acid methylglucoside, polyethylene glycol distearic acid, tetradecenesulfonate,
myristates, and myristyldimethylamine are useful in cleaning applications from the
viewpoint of increasing the viscosity and foaming action, and the anionic and cationic
surfactants are very useful from the viewpoint of further decreasing irritation.
Examples
[0100] The present invention will be described below in further detail using examples.
Evaluation of the test samples for both the examples of the present invention and the
comparative examples was carried out as shown below.
[0101] 1. Skin Barrier Function Recovery Ratio
The skin barrier recovery ratio is defined as shown below using the transepidermal
water loss (TEWL (g/Hr-m2)), and evaluated based on the following criteria. The
TEWL was measured using a Cutometer MPA 580 manufactured by COURAGE +
KHAZAKA Electronic GMBH Corp..
(Definition of Skin Barrier Function Recovery Ratio)
TEWL recovery ratio (%)=[((TEWLsds) - (TEWL over time))/((TEWLSDs) - (TEWLo))] x
100
Herein, TEWI_o,TEWLSds, and TEWL over time are defined as shown below.
TEWLo: The TEWL was measured on the forearm of a panel of 5 healthy males. TE
WI_o was defined as the initial average value of TEWL for the panel.
TEWLsds: A 5 mass% concentration of sodium lauryl sulfate (SDS) was applied to
the forearm of each panel member in order to induce a condition of reduced skin
barrier function and rough dry skin, and then the TEWL value was measured. The
average value for the TEWL at this time was defined as TEWLsds- This SDS
process was carried out to the extent that the average value of TEWL changed from
7 g/m2hr for the healthy skin to 14 -17 g/m2hr for rough dry skin.
TEWL over time: 2 uL/cm2 of test sample at an appropriate concentration was
openly applied twice a day to the aforementioned rough skin, and the TEWL was
measured over time for four days. The average value for the TEWL at this time was
defined as TEWL over time.
(Skin Barrier Function Recovery Ratio Evaluation Criteria)
Skin barrier function recovery ratio is 60% or higher: ®
Skin barrier function recovery ratio is 40% or higher and less than 60%: O
Skin barrier function recovery ratio is 20% or higher and less than 40%: A
Skin barrier function recovery ratio is less than 20%: x
[0102] 2. Horny layer Condition
Rough dry skin condition was induced in the same way as the evaluation for the skin
barrier function recovery rate on the forearm of 5 healthy males, and then the test
sample was openly applied, and the condition of the horny layer was observed four
days later using a microscope (trademark, USB Microscope M2-S; manufactured by
Scalar Corp.) at a zoom of 50X. The condition of the horny layer that was observed
in this manner was evaluated according to the following criteria, and based on the
average value of a panel of five persons, and evaluation of O was made if the
average value was less than 1 point, A if the average value was 1 or higher but less
than 2, and x if the average value was 2 or higher.
Homy layer cells, skin ridges, skin grooves are clearly arranged: 0 points
Horny layer cells, skin ridges, skin grooves are arranged: 1 points
Horny layer cells, skin ridges, skin grooves are somewhat irregular: 2 points
Horny layer cells, skin ridges, skin grooves are visible but irregular: 3 points
Horny layer cells, skin ridges, skin grooves are blurred and irregular: 4 points
[0103] 3. Human Patch Results
0.1 g of test sample was impregnated into wax paper of 1 cm2, and plastered in a
covered condition on healthy skin on the forearm of a panel of 5 healthy males for 24
hours. After 24 hours, the TEWL was measured and the results of this human patch
test were evaluated by the following criteria. A large increase rate in TEWL means
that the sample tends to destroy the barrier function and cause rough dry skin.
O: Average increasing rate of TEWL is below 10%
A: Average increasing rate of TEWL is 10% or higher, but less than 30%
x: Average increasing rate of TEWL is 30% or higher
[0104] 4. Uniformity, Smoothness, and Stylability of Hair
The test sample was thoroughly applied to a bundle of damaged hair that was
prepared by the method shown below, which was then blow dried while combing.
Evaluation was carried out by a panel of 10 persons from the viewpoint of "uniformity
from hair roots to hair tips", "smoothness of the hair", and the "stylability of the hair".
The evaluation criteria for "uniformity from hair roots to hair tips", "smoothness of the
hair", and the "stylability of the hair" was as shown below.
7 or more persons gave an assessment of "good": O
From 4 to 6 persons gave an assessment of "good": A
3 or less persons gave an assessment of "good": x
(Method for Preparing Damaged Hair)
A bundle of damaged hair was prepared by repeating 4 cycles of a process
consisting of applying a permanent wave treatment, brushing 100 times, bleaching,
brushing 100 times,to a bundle of healthy hair (15 cm, 1 g).
[0105] 5. Hair Damage Recovery Ratio
The hair damage recovery rate was defined by the following formula using damage
recovered hair prepared by immersion in a test sample for 1 minute and then drying
the aforementioned damaged hair.
Hair damage recovery ratio (%) = tensile strength of damage recovered hair/tensile
strength of healthy hair x 100
Wherein the tensile strength is defined as the breaking strength per unit cross-
section area, and the breaking strength and the cross-section area of the hair are
measured as shown below.
(a) Breaking Strength
The breaking strength was determined using a tensilon tensile tester.
¦ Tensile speed- ¦ -20 mm/min
• Test hair length- ¦ -40 mm
¦ Chart speed ¦• ¦ 100 mm/min
• N number = 5
(b) Cross-sectional area of a hair
After having measured the breaking strength, the hair was cut at a position
approximately 20 mm from the tip using a razor, and the area was determined by
measuring a microscope image.
6. Liquid Crystal Condition
A test sample was dispersed by heating, and then observed at a magnification of 40X
using a cross nicol polarized light microscope (CX31-P manufactured by Olympus
Corporation), and the liquid crystal condition was evaluated according to the following
criteria.
30 or more maltese cross images can be observed from all view ®
Maltese cross images can be observed from all view, but ® conditions not met
Maltese cross image can be observed depends on view A
Maltese cross image cannot be observed from any view x
[0106] [Acyl Compound Manufacturing 1]
9.1 g of L-lysine monohydrochloride (0.05 mol) was blended with 57 g of water. This
solution was adjusted to a pH of 10 - 11 with a 25% aqueous solution of sodium
hydroxide, while maintaining the reaction temperature at 5°C, and a reaction was
carried out by adding 31.1 g (0.1 mol) of N-lauroyl-L-glutamic anhydride over 2 hours
while stirring. After continuous stirring of the solution for 2 hours, tertiary butanol was
added until the concentration in the solution was 20 mass%, and then 75% sulfuric
acid was added in drops to adjust the pH to 2, and the temperature of the solution
was adjusted to 65°C. After the addition of the sulfuric acid was complete, stirring
was stopped, the solution was allowed to sit for 20 minutes at 65°C, and then the
solution separated into an organic layer and an aqueous layer, and the organic layer
was separated. Tertiary butanol and water were added to the separated organic
layer, and the temperature was maintained at 65°C while stirring for 20 minutes.
After stopping stirring, the solution was allowed to sit and separate into an organic
layer and an aqueous layer. After repeating the same water washing operation on
the organic layer obtained, the solvent was removed from the organic layer, and then
the solution was neutralized to a pH of 6.7 (25°C) using sodium hydroxide followed
by adjusting to a solid content of 30 mass%, and the solution was dried to obtain the
compounds (mixtures) expressed in the following formula (5).
[0107]
[C20]
The compounds (mixture) as expressed in the following formula (6) were obtained
using the same method and conditions as example 1, with the exception that 31.1 g
of N-lauroyl-L-glutamic anhydride was replaced with 39.5 g (0.1 mol) of N-stearoyl-L-
glutamic anhydride, and instead of neutralizing the pH of the solution to 6.7 (25°C)
and adjusting the solid content to 30 mass%, the pH was neutralized to 7 (60°C), and
the solid content was adjusted to 20 mass%.
[0110]
[C21]
[0112] [Acyl Compound Manufacturing 3]
The compounds (mixture) as shown in the following formula (7) were obtained using
the same method and conditions as example 1, with the exception that the 31.1 g of
N-lauroyl-L-glutamic anhydride was replaced with 31.1 g (0.1 mol) of N-cocooyl-L-
glutamic anhydride, and potassium hydroxide was used for neutralization when the
solution was neutralized and adjusted to a solid content of 30 mass% and a pH of 6.7
(25°C).
[0113]
[C22]
[0115] [Examples 1 through 9 and Comparative Examples 1 through 6]
The components shown in Table 1 were combined in the amounts (mass parts)
shown in Table 1 to prepare body surface protecting compositions for examples 1
through 9 and comparative examples 1 through 6. (Total amount was 100 parts,
remainder was purified water). The skin barrier function recovery ratio and the
condition of each layer was evaluated for each body surface protecting composition.
The results are shown in Table 1.
[0117] [Examples 10 through 12 and Comparative Examples 7 through 9]
Body surface protecting composition were prepared by combining the components
shown in Table 2 in the amount (mass part) shown in Table 2. A human patch test
was performed and the effect on the barrier function was confirmed for each
i composition for protecting human body surface. The results are shown in Table 2.

mass%.
[0119] Compositions containing the multi-chain multiple hydrophilic group-type
D compound of manufacturing examples 1 through 3 were confirmed as not having a
negative effect on the barrier function. On the other hand, a composition containing
sodium lauroyl glutamate, a composition containing sodium lauroyl glutamate and
lysine, and a composition containing potassium cocoyl glycine, which are single
chain-type compounds that have basic constitutional units similar to the multi-chain
multiple hydrophilic group-type compounds of examples 1 and 3 were confirmed as
degrading the barrier function.
[0120] From the above, it was confirmed that multi-chain multiple hydrophilic group-
type compounds have an effect on improving the barrier function of skin and hair
originating from their overall structure.
[0121] [Example 13]
A cream was prepared as shown below. Stability, skin irritability, and effect of
improving the horny layer condition of the cream were all favorable.
(Component) (mass parts)
(1) Stearic acid 6
(2) Cetyl alcohol 4
(3) Butyl stearate 6
(4) Propylene glycol 5
(5) Glycerin monostearate 2
(6) potassium hydroxide 0.3
(7) Acyl compound of manufacturing 1 1
(8) Perfume as appropriate
(10) Preservative and antioxidant as appropriate
(11) Purified water 75.7
[0122] [Example 14]
A cream was prepared as shown below. Stability, skin irritability, and effect of
improving the horny layer condition of the cream were all favorable.
(Component) (mass parts)
(1) Stearic acid 2
(2) Stearyl alcohol 5
(3) Hydrated lanolin 4
(4)Squalane 10
(5) Octyldodecanol 9
(6) 1,3-butylene glycol 6
(7) polyethylene glycol (mw 1500) 5
(8) Acyl compound of manufacturing 2 0.5
(9) Perfume as appropriate
(10) Preservative and antioxidant as appropriate
(11) Purified water 53
[0123] [Example 15]
A lotion was prepared as shown below. Stability, skin irritability, and effect of
improving the horny layer condition of the lotion were all favorable.
(Component) (mass parts)
(1) Stearic acid 2
(2) Cetyl alcohol 1.5
(3) Vaseline 4
(4) Squalane 4
(5) Glycerol tri-2-ethylhexanoate ester 3
(6) Dipropylene glycol 5
(7) polyethylene glycol (mw 1500) 3
(8) Acyl compound of manufacturing 3 1
(9) Triethanolamine 1
(10) Perfume as appropriate
(11) Preservative and antioxidant as appropriate
(12) Purified water 75.5
[0124] [Example 16]
An emulsion was prepared as shown below. Stability, skin irritability, and effect of
improving the horny layer condition of the emulsion were all favorable.
(Component) (mass parts)
(1) Cetyl alcohol 1
(2) Beeswax 0.5
(3) Vaseline 2
(4) Squalane 5
(5) Dimethyl polysiloxane 3
(6) Ethanol 5
(7) Glycerin 5
(8) Acyl compound of manufacturing 1 1
(9) 1,3-butylene glycol 3
(10) Carboxyvinyl polymer 0.2
(11) Perfume as appropriate
(12) Preservative and antioxidant as appropriate
(13) Purified water 74.3
[0125] [Example 17]
A gel was prepared as shown below. Stability, skin irritability, and effect of improving
the horny layer condition of the gel were all favorable.
(Component) (mass parts)
(1) polyethylene glycol (mw 1500) 9
(2) Dipropylene glycol 7
(3) Methyl cellulose 0.2
(4) Carboxyvinyl polymer 0.4
(5) Acyl compound of manufacturing 3 1
(6) potassium hydroxide 0.1
(7) Perfume as appropriate
(8) Preservative and antioxidant as appropriate
(9) Chelating agent as appropriate
(10) Purified water 82.3
[0126] [Example 18]
A facial mask was prepared as shown below. Stability, skin irritability, and effect of
improving the horny layer condition of the facial mask were all favorable.
(Component) (mass parts)
(1)1,3-butylene glycol 5
(2) Polyvinyl alcohol 15
(3) Carboxymethyl cellulose 5
(4)Ethanol 12
(5) Acyl compound of manufacturing 1 1
(6) Preservative as appropriate
(7) Perfume as appropriate
(8) Purified water amount to make the total 100 parts
[0127] [Example 19]
A lotion was prepared as shown below. Stability, skin irritability, and effect of
improving the horny layer condition of the lotion were all favorable.
(Component) (mass parts)
(1)Ethanol 55
(2) Dipropylene glycol 2.5
(3) Acyl compound of manufacturing 2 1
(4) Antimicrobial agent as appropriate
(5) Perfume as appropriate
(6) Purified water to make 100 parts
L0128] [Examples 20 through 24, Comparative Examples 10, 11]
(Preparation of Body surface protecting composition for Example 20 and
Comparative Example 10)
The body surface protecting composition for example 20 was prepared by combining
the components in the amount (mass part) shown in Table 3. Comparative Example
10 contained only purified water.[0129] (Preparation of Body surface protecting
composition for Examples 21 through 23 and Comparative Example 11)
The body surface protecting compositions for Example 21 through 23 were prepared
by combining the components shown in Table 3 and the following Base Emulsion A
in the amount (mass part) shown in Table 3. Base Emulsion A was used alone as
the Comparative Example 11.
(Base Emulsion A)
Liquid paraffin 10 mass parts
SEF-320A (product of Nihon Emulsion Co. Ltd.) 3 mass parts
1,3-butylene glycol 5 mass parts
Cetyl alcohol 2 mass parts
Water remainder
[0130] (Preparation of Body surface protecting composition for Example 24)
The body surface protecting composition for Example 24 was prepared by combining
the components shown in Table 3 and the following Base Emulsion B in the amount
(mass part) shown in Table 3.
(Base Emulsion B)
Squalane 10 mass parts
1,3-butylene glycol 5 mass parts
Cetyl alcohol 2 mass parts
Water remainder
[0131] (Evaluation)
The skin barrier function recovery ratio, hair uniformity, smoothness, and stylability,
and liquid crystal condition were evaluated for Examples 20 through 24 and
Comparative Examples 10 and 11. The results are shown in Table 3.
[0133] Formation of liquid crystal was confirmed in the compositions of Examples 20
through 22 and 24, and in particular, formation of spherical crystals were clearly
confirmed in the compositions of Examples 21, 22, and 24.
[0134] From the above, it was confirmed that a body surface protecting composition
containing multi-chain multiple hydrophilic group-type compound (A) of the present
invention formed liquid crystals, and it was also confirmed that the formation of liquid
crystal was facilitated when the composition also contained oil-based component (B).
Furthermore, when liquid crystals were formed, in addition to the function of
accelerating skin barrier recovery, the effect of improving hair, particularly hair tips,
that had been damaged was also confirmed.
[0135] Example 25
Body surface protecting compositions were prepared by combining the components
shown in Table 4 in the amount (mass part) shown in Table 4. The liquid crystal
condition of these compositions was evaluated. The results are shown in Table 4.

Observations were made at 40X zoom using a cross nicol polarized light microscope.
®: 30 or more maltese cross images can be observed from all view
O: Maltese cross images can be observed from all view
A: Maltese cross image can be observed depends on view
x: Maltese cross image can not be observed from any view
[0137] Formation of liquid crystals was confirmed in the composition where
cholesterol (molecular weight 387) and lauric acid (molecular weight 200) were
added with a molar ratio to a multi-chain multiple hydrophilic group-type compound
(molecular weight 835) of from 1/50 to 50/1, and in particular, formation was clearly
confirmed in the composition with a molar ratio of from 1/10 to 10/1, and very
remarkable formation of liquid crystals was confirmed in the composition with a molar
ratio of from 1/5 to 5/1.
[0138] From the above, it was confirmed that a composition containing multi-chain
multiple hydrophilic group-type compound (A) of the present invention could easily
form a liquid crystal composition if oil-based component (B) was used in combination
in a specific range within the ratio.
[0139] [Examples 26 through 28, Comparative Examples 12]
Body surface protecting compositions were prepared by combining the components
shown in Table 5 in the amount (mass part) shown in Table 5. Comparative Example
12 was purified water alone. The hair damage recovery rate was measured for each
composition. The results are shown in Table 5.
have an excellent effect of improving hair that has been damaged, and that effect will
be increased if an oil-based component (B) is used in combination.
INDUSTRIAL APPLICABILITY
[0142] The body surface protecting composition of the present invention will
accelerate recovery of the barrier function of skin and hair when that function has
deteriorated due to skin trouble or the like and will prevent degradation of the barrier
function, and therefore can be used by adding to cosmetic compositions,
pharmaceutical compositions, and body surface protecting agents and the like.
WE CLAIM:
1. A hair protecting agent comprising, at least one type of compound (A) that
is a multi-chain multiple hydrophilic group-type compound expressed by
the following formula (1) having two or more hydrophobic groups and two
of more hydrophilic groups in the molecule, wherein at least one of the
hydrophobic groups is an acyl group, and at least one of the hydrophilic
groups is a carboxyl group, a sulfonate group, a sulfate ester group, a
phosphate ester group, or a salt thereof;

(In formula (1), X represents a spacer with a molecular weight of one
million or less, has m functional group residues that may be the same or
different, and may have other functional groups, Q represents a functional group
expressed by the following formula (2), and the functional groups may be the
same or different;

in formula (2), Z represents a site of a bonding with a functional group residue
contained in X, R1 represents a hydrocarbon group that may be substituted with
a saturated or unsaturated substitution group of from 2 to 20 carbon atoms, R2
represents a hydrogen atom or a lower alkyl group of from 1 to 3 carbon atoms
which may also be substituted with a substitution group, and Y represents a
carboxyl group, a sulfonate group, a sulfate ester group, a phosphate ester
group, or a salt thereof, j and k independently represent either 0.1, or 2, but j and
k cannot both be 0 at the same time, n is an integer from 2 to 20, furthermore, m
is an integer such that m>n).
2. The hair protecting agent as claimed in claim 1, wherein at least one type of
said multi-chain multiple hydrophilic group-type compound is a compound
having an amino acid residue in the molecule.
3. The hair protecting agent as claimed in claim 1 or 2, wherein at least one
type of said multi-chain multiple hydrophilic group-type compound is a
compound expressed by said formula (1) having 2 hydrophobic groups and 3
hydrophilic groups in the molecule, and the number of carbon atoms in X
shown in said formula (1) is from 1 to 40.
4. The hair protecting agent according to any one of Claims 1 through 3,
wherein at least one type of said multi-chain multiple hydrophilic group
compound is a compound expressed by the following formula (3)

(In formula (3), R11 and R12 each independently represent a hydrocarbon group
which may be substituted with a saturated or unsaturated substitution group of
from 8 to 20 carbon atoms, R21 and R22 each independently represent either a
hydrogen atom or a lower alkyll group of from 1 to 3 carbon atoms that may be
substituted with a substitution group, each Y' independently represents a
carboxyl group or a salt thereof, each W independently represents -O-, -S-, or -
NR'- (where R' represents a hydrogen atom or a hydrocarbon group of from 1 to
10 carbon atoms which may be substituted with a substitution group), and T
represents a spacer of from 1 to 20 carbon atoms. j1,j2,k1and k2 independently
represent either 0, 1, or 2, but j1 and k1, and j2 and k2 cannot both be 0 at the
same time.).
5. The hair protecting agent as claimed in any one of claims 1 through 4, wherein
said (A) forms liquid crystals.
6. The hair protecting agent as claimed in any one of claims 1 through 5, further
comprising, (B) at least one type of oil-based component.
7. The hair protecting agent as claimed in claim 6, wherein said oil-based
component is a liquid crystal forming aid.
8. The hair protecting agent as claimed in claim 7, wherein said liquid crystal
forming aid comprises at least one type of sterol compound.
9. The hair protecting agent as claimed in claim 8, wherein said sterol compound
is at least one selected from a group consisting of cholesterol, cytosterol,
lanosterol, phytosterol, dihydrolanosterol, dehydrocholestetol and esters
thereof.
10. The hair protecting agent as claimed in any one of claims 7 through to 9,
wherein said liquid crystal forming aid is at least one selected from a group
consisting of fatty acids and salts thereof.
11. The hair protecting agent as claimed in claim 10, wherein said fatty acid is a
fatty acid of 6 or more and 22 or less carbon atoms.
12. The hair protecting agent as claimed in claim 10, wherein said fatty acid is a
fatty acid of 8 or more and 16 or less carbon atoms.
13. The hair protecting agent as claimed in any one of claims 1 to 12, wherein
the molar ratio of said liquid crystal forming aid to (A) (amount of liquid
crystal forming aid: amount of (A)) is 1:10 or higher and 10:1 or lower.
14. The hair protecting agent as claimed in any one of claims 1 to 12, wherein
the molar ratio of said liquid crystal forming aid to (A) (amount of liquid
crystal forming aid: amount of (A)) is 1:5 or higher and 5:1 or lower.
15. The hair protecting agent as claimed in any one of claim 1 through 14, further
comprising (C) a horny layer intercellular component and/or (D) a water
soluble moisturizing agent.



A body surface protecting composition, comprising at least one type of multi-
chain multiple hydrophilic group-type compound having two or more hydrophobic
groups and two or more hydrophilic groups in the molecule, which has an
excellent effect of accelerating the recovery of the barrier function of skin and
hair and preventing degradation of that function.

Documents:

04874-kolnp-2007-abstract.pdf

04874-kolnp-2007-claims 1.0.pdf

04874-kolnp-2007-claims 1.1.pdf

04874-kolnp-2007-correspondence others.pdf

04874-kolnp-2007-description complete.pdf

04874-kolnp-2007-form 1.pdf

04874-kolnp-2007-form 13.pdf

04874-kolnp-2007-form 2.pdf

04874-kolnp-2007-form 3.pdf

04874-kolnp-2007-form 5.pdf

04874-kolnp-2007-gpa.pdf

04874-kolnp-2007-international publication.pdf

04874-kolnp-2007-international search report.pdf

04874-kolnp-2007-others.pdf

04874-kolnp-2007-pct priority document notification.pdf

04874-kolnp-2007-pct request form.pdf

4874-KOLNP-2007-ABSTRACT 1.1.pdf

4874-KOLNP-2007-ABSTRACT.pdf

4874-KOLNP-2007-AMANDED CLAIMS 1.1.pdf

4874-KOLNP-2007-AMANDED CLAIMS.pdf

4874-KOLNP-2007-CORRESPONDENCE 1.2.pdf

4874-KOLNP-2007-CORRESPONDENCE OTHERS 1.1.pdf

4874-KOLNP-2007-CORRESPONDENCE.pdf

4874-KOLNP-2007-DESCRIPTION (COMPLETE) 1.1.pdf

4874-KOLNP-2007-DESCRIPTION (COMPLETE).pdf

4874-KOLNP-2007-EXAMINATION REPORT.pdf

4874-KOLNP-2007-FORM 1.1.1.pdf

4874-KOLNP-2007-FORM 1.pdf

4874-KOLNP-2007-FORM 13.pdf

4874-KOLNP-2007-FORM 18.pdf

4874-KOLNP-2007-FORM 2.1.1.pdf

4874-KOLNP-2007-FORM 2.pdf

4874-KOLNP-2007-FORM 3 1.1.pdf

4874-KOLNP-2007-FORM 3.pdf

4874-KOLNP-2007-FORM 5.pdf

4874-KOLNP-2007-GPA.pdf

4874-KOLNP-2007-GRANTED-ABSTRACT.pdf

4874-KOLNP-2007-GRANTED-CLAIMS.pdf

4874-KOLNP-2007-GRANTED-DESCRIPTION (COMPLETE).pdf

4874-KOLNP-2007-GRANTED-FORM 1.pdf

4874-KOLNP-2007-GRANTED-FORM 2.pdf

4874-KOLNP-2007-GRANTED-SPECIFICATION.pdf

4874-KOLNP-2007-OTHERS.pdf

4874-KOLNP-2007-PETITION UNDER RULE 137.pdf

4874-KOLNP-2007-PRIORITY DOCUMENT.pdf

4874-KOLNP-2007-REPLY TO EXAMINATION REPORT 1.1.pdf

4874-KOLNP-2007-REPLY TO EXAMINATION REPORT.pdf


Patent Number 250658
Indian Patent Application Number 4874/KOLNP/2007
PG Journal Number 03/2012
Publication Date 20-Jan-2012
Grant Date 17-Jan-2012
Date of Filing 14-Dec-2007
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 KENTAROU KANDA 1-2, YURAKU-CHO 1-CHOME, CHIYODA-KU, TOKYO 100-8440
2 YAMATO SAITOU 1-2, YURAKU-CHO 1-CHOME, CHIYODA-KU, TOKYO 100-8440
3 YUKIO YAMAWAKI 1-2, YURAKU-CHO 1-CHOME, CHIYODA-KU, TOKYO 100-8440
PCT International Classification Number A61K 8/44, A61Q 5/00
PCT International Application Number PCT/JP2006/311789
PCT International Filing date 2006-06-13
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2005-173233 2005-06-14 Japan
2 2005-235803 2005-08-16 Japan