WO2011004589A1 - 乳化組成物 - Google Patents
乳化組成物 Download PDFInfo
- Publication number
- WO2011004589A1 WO2011004589A1 PCT/JP2010/004414 JP2010004414W WO2011004589A1 WO 2011004589 A1 WO2011004589 A1 WO 2011004589A1 JP 2010004414 W JP2010004414 W JP 2010004414W WO 2011004589 A1 WO2011004589 A1 WO 2011004589A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- component
- hydrogen atom
- carbon atoms
- composition according
- Prior art date
Links
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Definitions
- the present invention relates to an emulsified composition that leaves moisture on the skin for a long time.
- the ⁇ -gel is a hydrated crystal structure and has a lamellar structure. Most of stratum corneum intercellular lipids present in the outermost stratum corneum of skin have this ⁇ -gel structure. And it has the function of maintaining the softness and smooth appearance of the skin by suppressing the invasion of substances from the outside and the moisture transpiration from the inside as well as holding the moisture itself. . In the skin, the stratum corneum retains about 33% of water in the form of bound water, and intercellular lipids in the stratum corneum are about 13% of bound water (where bound water is bound to constituent molecules). It is reported that the water is retained (non-patent document 1).
- Patent Document 1 describes that an emulsified composition containing ceramides or the like forms an ⁇ -gel structure and has a high moisturizing effect.
- ceramides or the like forms an ⁇ -gel structure and has a high moisturizing effect.
- the skin surface is covered with such an ⁇ -gel, it is expected that, as with the stratum corneum intercellular lipid, it can contain a lot of water during drying and can maintain a moist feeling.
- low molecular weight compounds such as glycerin and amino acids
- high molecular weight compounds such as hyaluronic acid are compounds that have high moisture retention.
- the amount of water that a single-component aqueous solution can hold is about the amount of bound water, which is not sufficiently satisfactory as the water holding ability of the preparation.
- the ⁇ -gel as described above is expected to have water retention ability, but the solid fat component constituting the ⁇ -gel has a heavy feeling of use, and in order to further enhance the moisture retention ability, Simply increasing the amount of ingredients does not provide a good feeling of use, such as a sticky feeling.
- the present invention retains bound water and free water (water that is retained between lamella layers but not bound to lamella structure components) between layers of the lamellar structure formed by ⁇ -gel, and allows moisture to be retained for a long time.
- the present invention relates to an emulsified composition that remains on the skin and improves the condition of the skin.
- the present inventors can further increase the water-holding ability of ⁇ -gel by combining a specific sugar alcohol or a disaccharide or a trisaccharide with an ⁇ -gel designed to increase water holding ability. It was found that an emulsified composition that improves the skin condition by leaving moisture in the skin for a long time was obtained.
- the present invention includes the following components (A), (B), (C), (D), (E) and (F): (A) an organic compound having two or more hydroxyl groups, an organic compound having an inorganic value of 220 to 450 and an organic value of 300 to 1000; 0.001 to 10% by weight; (B) an organic compound having one hydroxyl group and having an inorganic value of 100 to 200 and an organic value of 280 to 700; 0.001 to 10% by weight; (C) General formula (2): (Wherein R 1 represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 4 to 30 carbon atoms, which may be substituted by a hydroxyl group, a carbonyl group or an amino group; A methylene group, a methine group or an oxygen atom; X 1 , X 2 and X 3 each independently represents a hydrogen atom, a hydroxyl group or an acetoxy group, and X 4 represents a hydrogen atom, an acetyl group or a
- X 4 represents an oxo group. When formed, X 3 is not present.); R 2 and R 3 each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; R 4 represents a hydroxyl group, a carbonyl group or an amino group.
- E one or more compounds selected from sugar alcohols selected from erythritol, threitol, xylitol and mannitol, disaccharides and trisaccharides
- the emulsified composition of the present invention forms a highly regular and uniform ⁇ -type structure mainly composed of the components (A), (B) and (C), and the emulsion composition has a higher water retention ability, Can remain on the skin for a long time, and the skin condition can be improved.
- the skin condition can be improved.
- an excellent penetration feeling and a long-lasting feeling of moisture can be obtained.
- a flexible lamellar film can be formed on the skin surface, moisture can be retained between the layers, and the skin protection effect can be enhanced.
- the component (A) used in the present invention is an organic compound having two or more hydroxyl groups, and has an inorganic value of 220 to 450 and an organic value of 300 to 1000. More preferable component (A) is an organic compound having an inorganic value of 220 to 340 and an organic value of 380 to 840, from the viewpoint of forming a lamellar structure with each component described later. An organic compound having a value of 250 to 340 and an organic value of 380 to 700.
- the inorganic value and the organic value are obtained based on an organic conceptual diagram (Akira Fujita, prediction of organic compounds and an organic conceptual diagram, chemistry area Vol. 11, No. 10 (1957) 719-725). The value of the inorganic value and organic value which are obtained.
- Component (A) includes those represented by the following general formula (1).
- Z 1 represents a structure having two or more hydroxyl groups in a glycerin, sorbitan, sorbitol or sucrose residue
- Y 1 represents an ester bond group or an ether bond group
- R represents the number of carbon atoms. 14 to 22 hydrocarbon groups
- n represents a number of 1 to 2
- the hydrocarbon group having 14 to 22 carbon atoms represented by R is preferably a linear hydrocarbon group, for example, a linear alkyl group such as a myristyl group, a palmityl group, a stearyl group, a behenyl group; a palmitoyl group, An oleyl group etc. are mentioned.
- Examples of the compound represented by the general formula (1) include glycerin monofatty acid ester, sorbitan monofatty acid ester, sorbitan difatty acid ester, sorbitol monofatty acid ester, sorbitol difatty acid ester, sucrose monofatty acid ester, glycerin monoalkyl ether, and the like. Can be mentioned.
- glycerin monofatty acid ester As the component (A), glycerin monofatty acid ester, glycerin monoalkyl ether, sorbitan monofatty acid ester and sorbitan difatty acid ester are preferable.
- glyceryl monopalmitate inorganic value 260, organic value 380
- glyceryl monostearate inorganic value 260, organic value 420
- glyceryl monobehenate inorganic value 260, organic value 500
- mono Cetyl 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), sorbitan distearate
- glyceryl monobehenate or monocetyl glyceryl ether is more preferable from the viewpoint of improving the formability and water retention of a
- component (A) one or more kinds can be used, and are contained in the total composition in an amount of 0.001 to 10% by weight, preferably 0.05 to 7% by weight, and further 0.1 to 3% by weight. This is more preferable because the water retention ability is increased.
- component (B) used in the present invention is an organic compound having one hydroxyl group and having an inorganic value of 100 to 200 and an organic value of 280 to 700. More preferable component (B) is an organic compound having an inorganic value of 100 to 182 and an organic value of 300 to 520 from the viewpoint of forming a lamellar structure with component (A) and each component described later. . Specific examples include one or more compounds selected from higher alcohols having 14 to 22 carbon atoms and sterols.
- the higher alcohol has 14 to 22 carbon atoms, more preferably 16 to 18 carbon atoms.
- 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
- oleyl alcohol inorganic value 102, organic value 360
- those having a linear alkyl group are preferred, and cetanol and stearyl alcohol are more preferred.
- examples of sterols include cholesterol (inorganic value 182 and organic value 520) and phytosterol.
- Phytosterol is a general term for plant sterols such as ⁇ -sitosterol, campesterol, stigmasterol, and brassicasterol, and the composition thereof is not limited.
- component (B) can be used, and it is contained in the total composition in an amount of 0.001 to 10% by weight, preferably 0.05 to 7% by weight, and further 0.1 to 3% by weight. This is more preferable because the moisture occlusion is increased.
- Component (C) The component (C) used in the present invention is a compound represented by the general formula (2).
- R 1 is a straight chain having 4 to 30 carbon atoms, preferably 7 to 22 carbon atoms optionally substituted with a hydroxyl group, optionally substituted with a hydroxyl group, a carbonyl group or an amino group, A branched or cyclic saturated or unsaturated hydrocarbon group or a hydrogen atom.
- Z represents a methylene group, a methine group or an oxygen atom.
- X 1 , X 2 and X 3 each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group. It is preferable that 0 to 1 of X 1 , X 2 and X 3 is a hydroxyl group and the remainder is a hydrogen atom. When Z is a methine group, only one of X 1 and X 2 is a hydrogen atom, and the other does not exist.
- X 4 is preferably a hydrogen atom or a glyceryl group.
- R 2 and R 3 represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group, preferred R 2 is a hydrogen atom or a hydroxymethyl group, and preferred R 3 is a hydrogen atom.
- R 4 is a straight chain, branched chain having 5 to 60 carbon atoms which may have an ether bond, an ester bond or an amide bond in the main chain, which may be substituted with a hydroxyl group, a carboxy group or an amino group.
- a cyclic saturated or unsaturated hydrocarbon group is shown.
- the hydroxyl group or amino group may be substituted a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 5 to 35 carbon atoms, or a hydroxyl group at the ⁇ position of the hydrocarbon group
- a straight-chain, branched or cyclic saturated or unsaturated fatty acid having 8 to 22 carbon atoms which may be substituted is an ester bond or an amide bond.
- the fatty acid to be bonded is preferably isostearic acid, 12-hydroxystearic acid or linoleic acid.
- R 5 represents a hydrogen atom, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an acetoxy group. It is a saturated hydrocarbon group.
- R 1 is a hydrogen atom and Z is an oxygen atom
- R 5 is a hydrocarbon group having a total carbon number of 10 to 30.
- R 1 is a hydrocarbon group
- R 5 is a hydrocarbon group having 1 to 8 carbon atoms in total.
- a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms in total which may be substituted with 1 to 3 groups selected from a hydroxyl group, a hydroxyalkoxy group and an alkoxy group are preferable.
- the hydroxyalkoxy group and the alkoxy group are preferably those having 1 to 7 carbon atoms.
- ceramides represented by the following general formula (3) or (4) are preferable.
- the compound represented by the general formula (3) may be a naturally-occurring ceramide or a synthetic product having the same structure.
- R 11 represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 7 to 19 carbon atoms which may be substituted by a hydroxyl group
- Z 1 represents a methylene group or a methine group
- X 5 , X 6 and X 7 each independently represents a hydrogen atom, a hydroxyl group or an acetoxy group
- X 8 represents a hydrogen atom or together with an adjacent oxygen atom, forms an oxo group.
- R 12 represents a hydroxymethyl group or an acetoxymethyl group
- R 13 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- R 14 has 5 to 30 carbon atoms which may be substituted by a hydroxyl group Whether it is a linear, branched or cyclic saturated or unsaturated hydrocarbon group Or an ester bond of a linear or branched saturated or unsaturated fatty acid having 8 to 22 carbon atoms which may be substituted with a hydroxyl group at the ⁇ terminal of the alkyl group; Indicates that it may be a bond.
- R 11 is a linear alkyl group having 7 to 19 carbon atoms, more preferably 13 to 15 carbon atoms;
- R 14 is a linear alkyl group having 9 to 27 carbon atoms which may be substituted by a hydroxyl group, or linoleic acid Is a straight-chain alkyl group having 9 to 27 carbon atoms bonded with an ester.
- X 8 preferably represents a hydrogen atom or forms an oxo group together with an oxygen atom.
- R 14 is preferably tricosyl, 1-hydroxypentadecyl, 1-hydroxytricosyl, heptadecyl, 1-hydroxyundecyl, or a nonacosyl group in which linoleic acid is ester-bonded to the ⁇ position.
- ceramide types 1 to 7 in which sphingosine, dihydrosphingosine, phytosphingosine or sphingadienin is amidated for example, J. Lipid Res., 24: 759 (1983), FIG. And J. Lipid. Res., 35: 2069 (1994), porcine and human ceramides described in FIG.
- N-alkyl compounds for example, N-methyl compounds
- These ceramides may be either natural (D ( ⁇ )) optically active or non-natural (L (+)) optically active, or a mixture of natural and non-natural. May be used.
- the relative configuration of the above compound may be a natural configuration, a non-natural configuration other than that, or a mixture thereof.
- compounds of CERAMIDE1, CERAMIDE2, CERAMIDE3, CERAMIDE5, CERAMIDE6II hereinafter referred to as INCI, 8th Edition
- INCI 8th Edition
- Such commercially available natural ceramides are Ceramide I, Ceramide III, Ceramide IIIA, Ceramide IIIB, Ceramide IIIC, Ceramide VI (above, Cosmo Farm), Ceramide TIC-001 (Takasago Inc.), CERAMIDE II (Quest International), DS-Ceramide VI, DS-CLA-Phytoceramide, C6-Phytoceramide, DS-ceramide Y3S (DOOSAN), CERAMIDE2 (Cedama).
- R 15 represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group or a hydrogen atom having 10 to 22 carbon atoms which may be substituted by a hydroxyl group
- X 9 represents a hydrogen atom
- R 16 is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 5 to 22 carbon atoms which may be substituted with a hydroxyl group or an amino group
- R 17 represents a hydrogen atom Or a hydroxyl group, a hydroxyalkoxy group, an alkoxy group or an acetoxy group which may be substituted is an alkyl group having 1 to 30 carbon atoms in total.
- R 16 includes nonyl, tridecyl, pentadecyl, an undecyl group in which linoleic acid is ester-bonded to the ⁇ -position, a pentadecyl group in which linoleic acid is ester-bonded to the ⁇ -position, a pentadecyl group in which 12-hydroxystearic acid is ester-bonded to the ⁇ -position, An undecyl group in which methyl branched isostearic acid is amide-bonded at the ⁇ position is preferred.
- R 17 is an alkyl having a total carbon number of 10 to 30, preferably a total carbon number of 12 to 20, which may be substituted by a hydroxyl group, a hydroxyalkoxy group, an alkoxy group or an acetoxy group when R 15 is a hydrogen atom.
- R 15 is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 10 to 22 carbon atoms which may be substituted with a hydroxyl group.
- Those showing a C1-C8 alkyl group which may be substituted by a hydroxyl group, a hydroxyalkoxy group, an alkoxy group or an acetoxy group are preferred.
- the hydroxyalkoxy group or alkoxy group for R 17 is preferably one having 1 to 7 carbon atoms.
- R 15 is a hexadecyl group
- X 9 is a hydrogen atom
- R 16 is a pentadecyl group
- R 17 is a hydroxyethyl group
- R 15 is a hexadecyl group
- X 9 is a hydrogen atom
- R 16 is R 16 Preferred are pseudoceramides having a nonyl group, R 17 is a hydroxyethyl group; or R 15 is a hexadecyl group, X 9 is a glyceryl group, R 16 is a tridecyl group, and R 17 is a 3-methoxypropyl group.
- R 15 is a hexadecyl group
- X 9 is a hydrogen atom
- R 16 is a pentadecyl group
- R 17 is a hydroxyethyl group (N- (hexadecyloxyhydroxypropyl) -N-hydroxyethylhexadecanamide). More preferred.
- One or more compounds of component (C) can be used, and are contained in the total composition in an amount of 0.001 to 10% by weight, preferably 0.05 to 7% by weight, and further 0.1 to 5% by weight. It is more preferable that the component (C) is sufficiently penetrated into the skin.
- Component (D) used in the present invention is one or more compounds selected from nonionic surfactants having a polyoxyethylene group of HLB 10 or higher, ionic surfactants, and sphingosine salts.
- the nonionic surfactant has a polyoxyethylene group and has a hydrophilicity of HLB 10 or more, preferably HLB 12.5 to 15.5.
- examples include polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid ester, alkyl polyoxyethylene glyceryl, polyoxyethylene alkyl ether, and the like. Of these, polyoxyethylene hydrogenated castor oil and polyoxyethylene sorbitan monostearate are preferred.
- examples of the ionic surfactant include anionic surfactants, cationic surfactants, and amphoteric surfactants.
- examples of the anionic surfactant include fatty acid salts having 12 to 24 carbon atoms such as sodium laurate, potassium palmitate and arginine stearate; alkyl sulfates such as sodium lauryl sulfate and potassium lauryl sulfate; polyoxyethylene lauryl sulfate Alkyl ether sulfates such as triethanolamine; N-acyl sarcosine salts such as sodium lauroyl sarcosine; fatty acid amide sulfonates such as sodium N-stearoyl-N-methyltaurine and sodium N-myristoyl-N-methyltaurine; mono Alkyl phosphates such as sodium stearyl phosphate; polyoxyethylene alkyl ethers such as sodium polyoxyethylene oleyl ether sodium and polyoxyethylene
- fatty acid salts having 12 to 24 carbon atoms having 12 to 24 carbon atoms, fatty acid amide sulfonates, polyoxyethylene alkyl ether phosphates, and long-chain N-acyl glutamates are preferred, and N-stearoyl-N-methyl taurate sodium, Preference is given to arginine N-stearoyl-L-glutamate and sodium polyoxyethylene stearyl ether phosphate.
- the cationic surfactant is preferably a quaternary ammonium salt, for example, an alkyltrimethylammonium salt such as stearium trimethylammonium chloride or lauryltrimethylammonium chloride; a dialkyldimethylammonium salt, a trialkylmethylammonium salt, an alkylamine salt, etc. Is mentioned.
- amphoteric surfactant examples include alkyl dimethylamine oxide, alkyl carboxy betaine, alkyl sulfo betaine, amide amino acid salt, alkyl amide propyl betaine, and alkyl amide propyl betaine is more preferable.
- sphingosine salts are composed of sphingosines and acidic substances.
- examples of the sphingosines include those represented by the general formula (5).
- R 21 represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 4 to 30 carbon atoms, which may be substituted by a hydroxyl group, a carbonyl group or an amino group;
- each of X 11 , X 12 and X 13 independently represents a hydrogen atom, a hydroxyl group or an acetoxy group, and
- X 14 represents a hydrogen atom, an acetyl group or a glyceryl group Together with an adjacent oxygen atom to form an oxo group (provided that when Y is a methine group, one of X 11 and X 12 is a hydrogen atom and the other does not exist.
- X 14 is an oxo group) when forming a, X 13 is absent);.
- R 22 and R 23 are each independently hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group;
- a number of R 1 are each independently hydrogen Whether it is an atom or an amidino group
- a linear or branched saturated or unsaturated hydrocarbon group having 1 to 8 carbon atoms which may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group; Indicates a number of 2 or 3; the broken line indicates that it may be an unsaturated bond)
- R 21 is a linear, branched chain having 4 to 30 carbon atoms, preferably 7 to 22 carbon atoms optionally substituted with a hydroxyl group, a carbonyl group or an amino group. It is a chain or cyclic saturated or unsaturated hydrocarbon group.
- a branched one is preferred.
- a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a 1-hydroxytridecyl group, a 1-hydroxypentadecyl group, an isohexadecyl group, and an isostearyl group are preferable.
- Y represents a methylene group (CH 2 ), a methine group (CH), or an oxygen atom.
- X 11 , X 12 and X 13 each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group, and X 14 represents an oxo group together with a hydrogen atom, an acetyl group, a glyceryl group or an adjacent oxygen atom.
- the substituent to be formed is shown.
- X 11 , X 12 and X 13 those in which 0 to 1 are hydroxyl groups, the remainder is a hydrogen atom, and X 14 is a hydrogen atom are preferred.
- Y is a methine group, only one of X 11 and X 12 is a hydrogen atom, and the other does not exist. Also, when X 14 forms an oxo group, X 13 does not exist.
- R 22 and R 23 each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group, and R 23 is preferably a hydrogen atom.
- A represents a number of 2 or 3
- R 1 represents R 24 and R 25 when a is 2
- R 1 represents R 24 , R 25 and R 26 when a is 3.
- R 24 , R 25 and R 26 are each independently a hydrogen atom or an amidino group, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group. 1 to 8 linear or branched, saturated or unsaturated hydrocarbon groups.
- the hydroxyalkoxy group which can be substituted with a hydrocarbon group is preferably a linear or branched hydroxyalkoxy group having 1 to 7 carbon atoms.
- the alkoxy group is preferably a linear or branched alkoxy group having 1 to 7 carbon atoms.
- R 24 , R 25 and R 26 include a hydrogen atom; a linear or branched alkyl group such as methyl, ethyl, propyl, 2-ethylhexyl and isopropyl; an alkenyl group such as vinyl and allyl; an amidino group; Methyl, 2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxy-3-methoxypropyl, 2,3,4,5,6-penta Hydroxyhexyl, 1,1-bis (hydroxymethyl) ethyl, 2- (2-hydroxyethoxy) ethyl, 2-methoxyethyl, 1-methyl-2-hydroxyethyl, 3-hydroxypropyl, 3-methoxypropyl, 1 , Hydroxy groups such as 1-bis (hydroxymethyl) -2-hydroxyethyl, hydroxyalkoxy And a hydrocarbon group having 1 to 8 carbon atoms substituted by
- a hydrogen atom or a hydroxyl group such as a methyl group, 2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 1,1-bis (hydroxymethyl) ethyl, 2- (2-hydroxyethoxy) ethyl, etc.
- An alkyl group which may be substituted with 1 to 3 groups selected from a group and a hydroxyalkoxy group is preferred.
- sphingosine represented by the general formula (5) naturally occurring sphingosine represented by the following general formula (6) or a synthetic product having the same structure, and derivatives thereof (hereinafter referred to as natural sphingosine) or Pseudo-type sphingosines having a sphingosine structure represented by the general formula (7) (hereinafter referred to as pseudo-type sphingosine) are preferable.
- natural sphingosine naturally occurring sphingosine represented by the following general formula (6) or a synthetic product having the same structure, and derivatives thereof (hereinafter referred to as natural sphingosine) or Pseudo-type sphingosines having a sphingosine structure represented by the general formula (7) (hereinafter referred to as pseudo-type sphingosine) are preferable.
- a natural sphingosine represented by the general formula (6) A natural sphingosine represented by the general formula (6)
- R 27 represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 7 to 19 carbon atoms which may be substituted by a hydroxyl group;
- Y 1 represents a methylene group or a methine group;
- X 15 , X 16 and X 17 each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group, and
- X 18 represents a hydrogen atom or together with an adjacent oxygen atom, forms an oxo group ( However, when Y 1 is a methine group, one of X 15 and X 16 represents a hydrogen atom and the other does not exist.When X 18 forms an oxo group, X 17 does not exist.);
- R 28 Represents a hydroxymethyl group or an acetoxymethyl group; each a 2 R 2 is independently a hydrogen atom or an amidino group, or has a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alk
- R 27 is preferably a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 7 to 19 carbon atoms, and more preferably a linear saturated or unsaturated hydrocarbon group having 13 to 15 carbon atoms. Is preferred. a is preferably 2 , and each R 2 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.
- natural sphingosine represented by the general formula (6) include natural sphingosine, dihydrosphingosine, phytosphingosine, sphingadienin, dehydrosphingosine, dehydrophytosphingosine, and N-alkyl derivatives thereof (for example, N-methyl form) and the like.
- These sphingosines may be either natural (D (+)) optically active or non-natural (L ( ⁇ )) optically active, or a mixture of natural and non-natural types. May be used.
- the relative configuration of the above compound may be a natural configuration, a non-natural configuration other than that, or a mixture thereof.
- PHYTOSPHINGOSINE (INCI name: 8th Edition) and the following formula are preferable.
- D-Sphingosine (4-Sphingenine) (SIGMA-ALDRICH), DS-phytosphingosine (DOOSAN), and phytosphingosine (Cosmo Farm).
- R 29 represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 10 to 22 carbon atoms which may be substituted with a hydroxyl group
- X 19 represents a hydrogen atom, an acetyl group or A glyceryl group
- a R 3 each independently represents a hydrogen atom or an amidino group, or a total carbon which may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group
- a linear or branched saturated or unsaturated hydrocarbon group of the number 1 to 8 and a represents a number of 2 or 3
- R 29 is preferably an isobranched alkyl group having 14 to 20 carbon atoms, and more preferably an isostearyl group.
- the isostearyl group is most preferably an isostearyl group obtained by using, as a raw material oil, an isosteal alcohol derived from a by-product during production of a dimer acid using a fatty acid derived from an animal or vegetable oil.
- R 3 represents R 30 and R 31
- R 3 is R 30 , R 31, and R 32 .
- R 30 , R 31 and R 32 are, for example, a hydrogen atom; a linear or branched alkyl group such as methyl, ethyl, propyl, 2-ethylhexyl and isopropyl; an alkenyl group such as vinyl and allyl; an amidino group; Methyl, 2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxy-3-methoxypropyl, 2,3,4,5,6-penta Hydroxyhexyl, 1,1-bis (hydroxymethyl) ethyl, 2- (2-hydroxyethoxy) ethyl, 2-methoxyethyl, 1-methyl-2-hydroxyethyl, 3-hydroxypropyl, 3-methoxypropyl, 1 , 1-bis (hydroxymethyl) -2-hydroxyethyl, etc., hydroxyl groups, hydroxyalkoxy groups and the like And an alkyl group having
- R 30 and R 31 are a hydrogen atom, and the other is 2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 1,1-bis (hydroxymethyl) ethyl, 2- ( A secondary amine which is 2-hydroxyethoxy) ethyl is preferred.
- the pseudo-sphingosine includes R 29 is an isostearyl group, X 19 is a hydrogen atom, R 30 is a hydrogen atom, R 31 is a 2-hydroxyethyl group, 1,1-bis (hydroxymethyl) ethyl group, 1,1 It is preferable that 1 to 3 selected from hydroxyl group and hydroxyalkoxy group such as dimethyl-2-hydroxyethyl group or 2- (2-hydroxyethoxy) ethyl group are substituted alkyl groups.
- Specific examples of the pseudo-sphingosine include the following pseudo-sphingosines (i) to (iv).
- sphingosines As the sphingosines, sphingosine, phytosphingosine and pseudo-sphingosine are preferable, and pseudo-sphingosine (ii) and 1- (2-hydroxyethylamino) -3-isostearyloxy-2-propanol are more preferable.
- Acidic substances constituting salts with these sphingosine, phytosphingosine and pseudo-sphingosine 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 Acid; oxycarboxylic acid such as citric acid, lactic acid, malic acid and the like.
- sphingosine, phytosphingosine, pseudo-type sphingosine (pseudo-type sphingosine (ii), 1- (2-hydroxyethylamino) -3-isostearyloxy-2-propanol) succinate, lactate, glutamic acid Salts are preferable, and sphingosine, phytosphingosine, and pseudo-sphingosine glutamate are more preferable.
- an anionic surfactant and a sphingosine salt from the viewpoint of water retention because a large amount of water can be held between layers of the lamella due to the effect of charge repulsion.
- an anionic surfactant and a sphingosine salt from the viewpoint of water retention because a large amount of water can be held between layers of the lamella due to the effect of charge repulsion.
- N-stearoyl-N-methyltaurine sodium, polyoxyethylene stearyl ether sodium phosphate, N-stearoyl-L-glutamate arginine, phytosphingosine glutamate, and pseudo-sphingosine glutamate are stable in small amounts. It is preferable at the point from which an emulsion is obtained.
- the component (D) one or more kinds can be used, and it is contained in the total composition in an amount of 0.00012 to 10% by weight, preferably 0.01 to 7% by weight, and further 0.2 to 3% by weight. Is preferable because it helps to widen the layer interval of the lamellar structure made of the components (A), (B), and (C) and to form a structure that stores a large amount of moisture between the layers.
- the sugar alcohol is selected from erythritol, threitol, xylitol and mannitol. Of these, xylitol is preferred.
- examples of the disaccharide and the trisaccharide include trehalose, galactosyl fructose, sucralose, melibiose, raffinose, and lactose. Of these, trehalose and raffinose are preferable, and trehalose is more preferable.
- component (E) one or more kinds can be used, and a sugar alcohol, a disaccharide and / or a trisaccharide can be used in combination.
- Component (E) is preferably contained in an amount of 0.003 to 15% by weight in the total composition because a high water retention ability is obtained.
- sugar alcohols it is preferably contained in an amount of 0.003 to 10% by weight, preferably 0.01 to 5% by weight, and more preferably 0.1 to 3% by weight in the total composition.
- a disaccharide or a trisaccharide it is preferable to contain 0.018 to 15% by weight, preferably 0.1 to 10% by weight, and more preferably 0.5 to 7% by weight in the total composition. Is preferred.
- (E) / ((A) + (B) + (C)) 0.2 or more, preferably 0.6 to 5.
- the lamellar structure formed by the components (A), (B) and (C) is firm, and the same lamellar flexible film is formed between cells on the skin after drying. Is formed, the moisture retention ability of the skin is increased, and a moist feeling is maintained, which is preferable.
- (D) / ((A) + (B) + (C)) 0.04 to 1, and more preferably 0.04 to 0.5 improves the permeability of component (C) and improves skin
- the moisturizing effect from the surface and the inside can be obtained, which is preferable.
- the water of component (F) is preferably contained in an amount of 20 to 99.9% by weight, preferably 40 to 95% by weight, and more preferably 50 to 90% by weight in the total composition.
- other aqueous bases such as lower alcohols having 1 to 4 carbon atoms such as ethanol and propanol may also be contained.
- component (A) is glyceryl monobehenate or monocetyl glyceryl ether
- component (B) is cetanol
- component (C) is a compound represented by general formula (2)
- component (D) is stearoyl glutamate or sphingosine salts
- component (E) is xylitol and the component (F) is water.
- the emulsion composition of the present invention can further contain an oily component.
- oily component for example, hydrocarbon oils such as liquid paraffin, squalane and petrolatum; ether oils such as cetyldimethylbutyl ether, ethylene glycol dioctyl ether and glycerol monooleyl ether; octyldodecyl myristate, isopropyl palmitate, butyl stearate, di-2 adipate -Ester oils such as ethylhexyl, neopentyl glycol dicaprate and trioctanoin; higher fatty acids such as stearic acid, behenic acid and isomyristinic acid; vegetable oils such as olive oil; dimethylpolysiloxane, cyclic dimethylpolysiloxane, methylphenylpolysiloxane, Amino-modified silicone, carboxy-modified silicone, alcohol-modified silicone, alkyl-
- Corn oil perfluoroalkylethyl phosphoric acid, perfluoroalkyl polyoxyethylene phosphoric acid, a perfluoropolyether, such as fluorine-based oils such as polytetrafluoroethylene. These oily components are preferably contained in the total composition in an amount of 0 to 20% by weight.
- the emulsified composition of the present invention is an active ingredient or additive used in normal cosmetics, for example, water-soluble vitamins such as ascorbic acid, nicotinic acid amide, and nicotinic acid; buckwheat extract, licorice extract, aloe extract, Animal and plant extracts such as horse chestnut extract, tea extract, cucumber extract, clove extract, carrot extract, cranberry extract, placenta extract, seaweed extract, maronier extract, yuzu extract, asunaro extract, royal jelly extract, eucalyptus extract, asunaro extract; 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; carboxyvinyl polymer, sodium alginate, carrageenan, carboxymethylcellulose, Increase of Roxyethylcellulose, Guar gum, Xanthan gum, Carboxymethylchitos
- the emulsion composition of the present invention can be produced by production methods (1) to (3).
- Production method (1) Components (A) to (D) (in the case of containing oily components, mixed components containing components (A) to (D) and oily components, and water containing components (E) and (F) A method of mixing and emulsifying phase components.
- Production method (2) A mixed component containing components (A) to (E) (in the case of containing oily components, components (A) to (E) and oily components) and an aqueous phase component containing component (F) A method of mixing and emulsifying.
- Production method (3) Components (A) to (D) (when oily components are included, components (A) to (D) and oily components) and a mixed component containing a part of component (E), and the remaining A method of mixing and emulsifying water phase components containing components (E) and (F).
- the production method (2) is more preferable because the water retention of the obtained emulsion composition is higher than that of the production method (1).
- the resulting emulsified composition is ⁇ -gel ( ⁇ -type crystal), and precipitation of crystals ( ⁇ -type crystal) is suppressed.
- the ⁇ -gel can be confirmed by structural analysis by X-ray.
- the ⁇ -type structure is a hexagonal system, and the lipophilic group is oriented perpendicular to the surface of the hydrophilic base layer, and a sharp single diffraction peak appears in the vicinity of a Bragg angle of 21-23 °. is there.
- the emulsified composition of the present invention is an oil-in-water emulsified composition, and is suitable for cosmetics such as lotions, emulsions, creams and gels, and external preparations for skin.
- Examples 1 to 10 and Comparative Examples 1 to 8 Oil-in-water emulsion compositions having the compositions shown in Table 1 and Table 2 were produced, and structural analysis and residual water content measurement were performed by X-ray. Moreover, the film forming property was evaluated. The results are shown in Table 1 and Table 2 together. In addition, it confirmed that the membrane
- Phase I components (mixed components including components (A) to (D)) were heated and mixed at 80 to 95 ° C., and this was mixed with Phase II heated to 80 to 95 ° C. with propeller stirring (300 rpm) (A mixed component containing components (E) and (F)) was added and emulsified, and gradually cooled to 25 ° C. to obtain an oil-in-water emulsion composition.
- Residual moisture measurement 2 g of the oil-in-water emulsion composition is spread uniformly on a 6 ⁇ 6 cm metal tray at a constant thickness, and the change in weight is plotted against time under a constant temperature and humidity of 25 ° C. and a humidity of 40%. At this time, bending occurs in two stages as shown in FIG. 1, and the weight change thereafter becomes extremely small due to the formation of the lamellar film.
- the residual water content was determined from the weight of the intersection of the straight line 1 and the straight line 2 in FIG. 1, and the water content relative to the solid content in the preparation was determined by the following formula.
- the solid content includes all components (A) to (E).
- Example 11 and Comparative Examples 9 to 11 An oil-in-water emulsion composition having the composition shown in Table 3 was produced in the same manner as in Examples 1 to 10, and the change in small-angle X-ray scattering intensity based on Comparative Example 9 was evaluated. The results are also shown in Table 3.
- Example 11 has high orderness of the lamellar structure because the small-angle X-ray scattering intensity is increased.
- Examples 54-56 About the oil-in-water type emulsion composition of the composition shown in Table 10, it manufactured according to manufacturing method (2), and about the obtained composition, respectively, the structural analysis by X-rays, residual moisture content, film-forming property, penetrating feeling, and moisture The sustainability of was evaluated. The results are also shown in Table 10. The same compositions as in Examples 54 to 56 and those produced by production method (1) (Examples 30, 3, and 5) are also shown.
- Manufacturing method (2) Phase I components (mixed components including components (A) to (E)) were heated and mixed at 80 to 95 ° C., and this was mixed with Phase II heated to 80 to 95 ° C. with propeller stirring (300 rpm) (Aqueous phase component containing component (F)) was added and emulsified, and gradually cooled to 25 ° C. to obtain an oil-in-water emulsion composition.
- Example 57 skin lotion
- an oil-in-water emulsified composition (lotion) having the composition shown in Table 11 was produced, and structural analysis was performed by X-ray to determine film formation, penetration, and moisture persistence. evaluated. The results are also shown in Table 11.
- Example 58 milky lotion
- an oil-in-water emulsion composition (emulsion) having the composition shown in Table 12 was produced, and structural analysis was performed by X-ray to evaluate film formation, penetration, and moisture persistence. did. The results are also shown in Table 12.
- Example 59 Translucent gel
- an oil-in-water emulsion composition having the composition shown in Table 13 was produced and subjected to structural analysis by X-ray to determine film-forming properties, permeation feeling and moisture retention. Evaluated. The results are also shown in Table 13.
- Example 60 (cream) In the same manner as in Examples 1 to 10, an oil-in-water emulsified composition (cream) having the composition shown in Table 14 was produced, and structural analysis was performed by X-ray to evaluate film formation, penetration, and moisture persistence. did. The results are also shown in Table 14.
- Example 61 The ingredients of Phase I were heated and mixed at 80 to 95 ° C., and then added with Phase II heated to 80 to 95 ° C. with propeller stirring (300 rpm), emulsified, and gradually cooled to 25 ° C.
- the phase III at 25 ° C. was added to produce an oil-in-water emulsion composition (lotion) having the composition shown in Table 15.
- the structural analysis by X-ray was performed, and film-forming property, a penetrating feeling, and the sustainability of moisture were evaluated. The results are also shown in Table 15.
- Example 62 Cosmetic liquid
- the ingredients of Phase I were heated and mixed at 80 to 95 ° C., and then added with Phase II heated to 80 to 95 ° C. with propeller stirring (300 rpm), emulsified, and gradually cooled to 25 ° C.
- the phase III at 25 ° C. was added to produce an oil-in-water emulsion composition (lotion) having the composition shown in Table 16.
- the structural analysis by X-ray was performed, and film-forming property, a penetrating feeling, and the sustainability of moisture were evaluated. The results are also shown in Table 16.
- Example 63 milky lotion
- an oil-in-water emulsion composition (emulsion) having the composition shown in Table 17 was produced, and structural analysis was performed by X-ray to evaluate film formation, penetration, and moisture persistence. did. The results are also shown in Table 17.
- Example 64 (cream) In the same manner as in Examples 1 to 10, an oil-in-water emulsion composition (cream) having the composition shown in Table 18 was produced, and structural analysis was performed by X-ray to evaluate film formation, penetration, and moisture persistence. did. The results are also shown in Table 18.
Abstract
Description
例えば、特許文献1には、セラミド類等を含有する乳化組成物が、α-ゲル構造を形成し、保湿効果が高いことが記載されている。このようなα-ゲルで皮膚表面を覆った場合、角層細胞間脂質と同様、乾燥時において、水分を多く含有でき、潤い感を持続できることが期待される。
(A)水酸基を2個以上有する有機化合物であって、無機性値が220~450、有機性値が300~1000である有機化合物 0.001~10重量%、
(B)水酸基を1個有する有機化合物であって、無機性値が100~200、有機性値が280~700である有機化合物 0.001~10重量%、
(C)一般式(2):
(D)ポリオキシエチレン基を有するHLB10以上の非イオン界面活性剤、イオン性界面活性剤及びスフィンゴシン塩類から選ばれる1種以上の化合物 0.00012~10重量%、
(E)エリスリトール、トレイトール、キシリトール及びマンニトールから選ばれる糖アルコール、2単糖並びに3単糖から選ばれる1種以上の化合物 0.003~15重量%、
(F)水
を含有する乳化組成物を提供するものである。
本発明で用いる成分(A)は、水酸基を2個以上有する有機化合物であって、無機性値が220~450、有機性値が300~1000である有機化合物である。成分(A)のより好ましいものとしては、後述する各成分とラメラ構造形成性の観点から、無機性値が220~340、有機性値が380~840である有機化合物で、更には、無機性値が250~340、有機性値が380~700である有機化合物である。
本発明において、無機性値、有機性値とは、有機概念図(藤田穆、有機化合物の予測と有機概念図、化学の領域Vol.11,No.10(1957)719-725)に基づき求められる無機性値及び有機性値の値をいう。
一般式(1)で表される化合物としては、グリセリンモノ脂肪酸エステル、ソルビタンモノ脂肪酸エステル、ソルビタンジ脂肪酸エステル、ソルビトールモノ脂肪酸エステル、ソルビトールジ脂肪酸エステル、ショ糖モノ脂肪酸エステル、グリセリンモノアルキルエーテル等が挙げられる。
成分(A)としては、グリセリンモノ脂肪酸エステル、グリセリンモノアルキルエーテル、ソルビタンモノ脂肪酸エステル及びソルビタンジ脂肪酸エステルが好ましい。中でも、モノパルミチン酸グリセリル(無機性値260、有機性値380)、モノステアリン酸グリセリル(無機性値260、有機性値420)、モノベヘン酸グリセリル(無機性値260、有機性値500)、モノセチルグリセリルエーテル(無機性値220、有機性値380)、モノステアリルグリセリルエーテル(無機性値220、有機性値420)、モノステアリン酸ソルビタン(無機性値445、有機性値480)、ジステアリン酸ソルビタン(無機性値340、有機性値840)が好ましく、後述するラメラ状の皮膜の形成性、保水性が向上する観点から、モノベヘン酸グリセリル又はモノセチルグリセリルエーテルがより好ましい。
本発明で用いる成分(B)は、水酸基を1個有する有機化合物であって、無機性値が100~200、有機性値が280~700である有機化合物である。成分(B)のより好ましいものとしては、成分(A)及び後述する各成分とラメラ構造形成性の観点から、無機性値が100~182、有機性値が300~520である有機化合物である。
具体的には、炭素数14~22の高級アルコール、ステロール類から選ばれる1種以上の化合物が挙げられる。
これらのうち、直鎖アルキル基を有するものが好ましく、更に、セタノール、ステアリルアルコールが好ましい。
本発明で用いる成分(C)は、前記一般式(2)で表わされる化合物である。
Zはメチレン基、メチン基又は酸素原子のいずれかを示す。
R2及びR3は、水素原子、ヒドロキシル基、ヒドロキシメチル基又はアセトキシメチル基を示し、好ましいR2は水素原子又はヒドロキシメチル基であり、好ましいR3は水素原子である。
(I)一般式(3)で表わされる化合物は、天然由来のセラミド類又は同構造の合成物であっても良い。
これらのセラミドは天然型(D(-)体)の光学活性体を用いても、非天然型(L(+)体)の光学活性体を用いても、更に天然型と非天然型の混合物を用いてもよい。上記化合物の相対立体配置は、天然型の立体配置のものでも、それ以外の非天然型の立体配置のものでも良く、また、これらの混合物によるものでもよい。これらのうち、CERAMIDE1、CERAMIDE2、CERAMIDE3、CERAMIDE5、CERAMIDE6IIの化合物(以上、INCI、8th Edition)及び次式で表わされるものが好ましい。
このような天然型セラミドの市販のものとしては、Ceramide I、Ceramide III、Ceramide IIIA、Ceramide IIIB、Ceramide IIIC、Ceramide VI(以上、コスモファーム社)、Ceramide TIC-001(高砂香料社)、CERAMIDE II(Quest International社)、DS-Ceramide VI、DS-CLA-Phytoceramide、C6-Phytoceramide、DS-ceramide Y3S(DOOSAN社)、CERAMIDE2(セダーマ社)が挙げられる。
また、成分(A)及び(B)の質量割合は、(A)/((A)+(B))=0.1以上、更に0.25~0.75であるのが、しっかりしたα-ゲル構造を作り、水分保持力を高めることができるので好ましい。
本発明で用いる成分(D)は、ポリオキシエチレン基を有するHLB10以上の非イオン界面活性剤、イオン性界面活性剤及びスフィンゴシン塩類から選ばれる1種以上の化合物である。
成分(D)の化合物のうち、非イオン界面活性剤は、ポリオキシエチレン基を有するもので、HLB10以上、好ましくはHLB12.5~15.5の親水性のものである。例えば、ポリオキシエチレン硬化ヒマシ油、ポリオキシエチレンソルビタン脂肪酸エステル、アルキルポリオキシエチレングリセリル、ポリオキシエチレンアルキルエーテル等が挙げられる。
これらのうち、ポリオキシエチレン硬化ヒマシ油、モノステアリン酸ポリオキシエチレンソルビタンが好ましい。
アニオン界面活性剤としては、例えば、ラウリン酸ナトリウム、パルミチン酸カリウム、ステアリン酸アルギニン等の炭素数12~24の脂肪酸塩;ラウリル硫酸ナトリウム、ラウリル硫酸カリウム等のアルキル硫酸エステル塩;ポリオキシエチレンラウリル硫酸トリエタノールアミン等のアルキルエーテル硫酸エステル塩;ラウロイルサルコシンナトリウム等のN-アシルサルコシン塩;N-ステアロイル-N-メチルタウリンナトリウム、N-ミリストイル-N-メチルタウリンナトリウム等の脂肪酸アミドスルホン酸塩;モノステアリルリン酸ナトリウム等のアルキルリン酸塩;ポリオキシエチレンオレイルエーテルリン酸ナトリウム、ポリオキシエチレンステアリルエーテルリン酸ナトリウム等のポリオキシエチレンアルキルエーテルリン酸塩;ジ-2-エチルヘキシルスルホコハク酸ナトリウム等の長鎖スルホコハク酸塩;N-ラウロイルグルタミン酸モノナトリウム、N-ステアロイル-L-グルタミン酸ナトリウム、N-ステアロイル-L-グルタミン酸アルギニン、N-ステアロイルグルタミン酸ナトリウム、N-ミリストイル-L-グルタミン酸ナトリウム等の長鎖N-アシルグルタミン酸塩などが挙げられる。
これらのうち、炭素数12~24の脂肪酸塩、脂肪酸アミドスルホン酸塩、ポリオキシエチレンアルキルエーテルリン酸塩、長鎖N-アシルグルタミン酸塩が好ましく、更に、N-ステアロイル-N-メチルタウリンナトリウム、N-ステアロイル-L-グルタミン酸アルギニン、ポリオキシチレンステアリルエーテルリン酸ナトリウムが好ましい。
X11、X12、及びX13は、各々独立して水素原子、ヒドロキシル基又はアセトキシ基を示し、X14は水素原子、アセチル基、グリセリル基、隣接する酸素原子と一緒になってオキソ基を形成する置換基を示す。X11、X12、及びX13のうち0~1個がヒドロキシル基で、残余が水素原子、及びX14が水素原子であるものが好ましい。なお、Yがメチン基のとき、X11とX12のいずれか一方のみが水素原子であり、他方は存在しない。また、X14がオキソ基を形成するとき、X13は存在しない。
(I)一般式(6)で表わされる天然型スフィンゴシン。
これらのスフィンゴシンは天然型(D(+)体)の光学活性体を用いても、非天然型(L(-)体)の光学活性体を用いても、更に天然型と非天然型の混合物を用いてもよい。上記化合物の相対立体配置は、天然型の立体配置のものでも、それ以外の非天然型の立体配置のものでも良く、また、これらの混合物によるものでもよい。
更に、PHYTOSPHINGOSINE(INCI名;8th Edition)及び次式で表わされるものが好ましい。
天然型スフィンゴシンの市販のものとしては、例えば、D-Sphingosine(4-Sphingenine)(SIGMA-ALDRICH社)、DS-phytosphingosine (DOOSAN社)、phytosphingosine(コスモファーム社)が挙げられる。
また、aが2のときR3はR30及びR31を示し、aが3のときR3はR30、R31及びR32である。
これらのうち、R30及びR31のいずれか1つが水素原子で、他方が2-ヒドロキシエチル、1,1-ジメチル-2-ヒドロキシエチル、1,1-ビス(ヒドロキシメチル)エチル、2-(2-ヒドロキシエトキシ)エチルである2級アミンが好ましい。
擬似型スフィンゴシンの具体例としては、次の擬似型スフィンゴシン(i)~(iv)が挙げられる。
成分(D)は、1種以上を用いることができ、全組成中に0.00012~10重量%含有され、好ましくは0.01~7重量%、更に0.2~3重量%含有されるのが、成分(A)、(B)及び(C)で作るラメラ構造の層間隔を広げ、層間に水分を多く蓄える構造を形成するのに役立つので好ましい。
本発明で用いる成分(E)のうち、糖アルコールは、エリスリトール、トレイトール、キシリトール及びマンニトールから選ばれるものである。これらのうち、キシリトールが好ましい。
また、2単糖、3単糖としては、例えば、トレハロース、ガラクトシルフルクトース、スクラロース、メリビオース、ラフィノース、ラクトース等が挙げられる。これらのうち、トレハロース、ラフィノースが好ましく、更にはトレハロースが好ましい。
成分(E)は、全組成中に0.003~15重量%含有されるのが、高い水分保持能が得られるので好ましい。
更に、糖アルコールの場合には、全組成中に0.003~10重量%含有するのが好ましく、0.01~5重量%、更に0.1~3重量%含有されるのが好ましい。
また、2単糖又は3単糖の場合には、全組成中に0.018~15重量%含有するのが好ましく、0.1~10重量%、更に0.5~7重量%含有されるのが好ましい。
更に、成分(E)が糖アルコールの場合には、(E)/((A)+(B)+(C))=0.01~3、更に0.125~2.5であるのが好ましい。また、2単糖又は3単糖の場合には、(E)/((A)+(B)+(C))=0.2以上、更に0.6~5であるのが好ましい。
成分(E)を含むことにより、成分(A)、(B)及び(C)で作るラメラ構造がしっかりし、乾燥後も皮膚上に細胞間に構成されると同様なラメラ状の柔軟な皮膜が形成され、皮膚の水分保持能が高まり、潤い感が持続するので好ましい。
また、(D)/((A)+(B)+(C))=0.04~1、更に0.04~0.5であるのが、成分(C)の浸透性を高め、皮膚表面と内部からの保湿効果を得ることができるので好ましい。
また、その他の水性基剤、例えばエタノール、プロパノール等の炭素数1~4の低級アルコールなどを含有することもできる。
更に、成分(A)がモノベヘン酸グリセリル又はモノセチルグリセリルエーテル、成分(B)がセタノール、成分(C)が一般式(2)で表される化合物、成分(D)がステアロイルグルタミン酸塩又はスフィンゴシン塩類、成分(E)がキシリトール、成分(F)が水であるものが、より好ましい。
製造方法(1):成分(A)~(D)(油性成分を含む場合は、成分(A)~(D)及び油性成分を含む混合成分と、成分(E)及び(F)を含む水相成分を混合して乳化させる方法。
製造方法(2):成分(A)~(E)(油性成分を含む場合は、成分(A)~(E)及び油性成分)を含む混合成分と、成分(F)を含む水相成分を混合して乳化させる方法。
製造方法(3):成分(A)~(D)(油性成分を含む場合は、成分(A)~(D)及び油性成分)と成分(E)の一部を含む混合成分と、残余の成分(E)及び(F)を含む水相成分を混合して乳化させる方法。
製造方法(2)は、製造方法(1)と比較して、得られる乳化組成物の保水性がより高いことから、より好ましい。
また、本発明の乳化組成物は、水中油型乳化組成物であり、例えば、化粧水、乳液、クリーム、ジェル等の化粧料や、皮膚外用剤として好適である。
表1及び表2に示す組成の水中油型乳化組成物を製造し、X線による構造解析及び残存水分量測定を行った。また、皮膜形成性を評価した。結果を表1及び表2に併せて示す。
なお、実施例で得られた皮膜は、透過型電子顕微鏡によりラメラ構造を有することを確認した。
製造方法(1):
第I相の成分(成分(A)~(D)を含む混合成分)を、80~95℃で加熱混合し、これに、プロペラ撹拌下(300rpm)、80~95℃に加熱した第II相(成分(E)、(F)を含む混合成分)を加えて乳化し、25℃まで徐々に冷却して、水中油型乳化組成物を得た。
(1)X線による構造解折:
得られた水中油型乳化組成物について、2θ=10~30°の広角X線回折ピークより、WilsonとOttの方法(Wilson,D.A. and Ott,E., J.Chem.Phys., 2, 231-238(1934))に従い、結晶構造を決定した。
6×6cmの金属トレーに、水中油型乳化組成物2gを一定厚みで均一に広げ、25℃、湿度40%の恒温恒湿下で、重量変化を時間に対してプロットする。このとき、図1のように2段階に屈曲が生じ、ラメラ皮膜の形成により、その後重量変化が極めて小さくなる。図1中の直線1と直線2の交点の重量から残存水分量を求め、製剤中の固形分に対する水分量を、以下の式で求めた。固形分には、成分(A)~(E)全ての成分を含む。
テフロン(登録商標)シャーレ(直径5cm)に5gの剤を入れ、均一に伸ばし、2日間乾燥させた際の皮膜の状態を観察した。
○:柔軟な皮膜が形成される。
△:硬くて脆い皮膜が形成される。
×:皮膜は形成されない。
表3に示す組成の水中油型乳化組成物を実施例1~10と同様にして製造し、比較例9を基準とした小角X線散乱強度の変化を評価した。結果を表3に併せて示す。
実施例1~10と同様にして、表4に示す組成の水中油型乳化組成物を製造し、X線による構造解析、残存水分量及び皮膜形成性を評価した。また、浸透感及び潤いの持続性を評価した。結果を表4に併せて示す。
使用感(浸透感/潤いの持続性):
10名の専門パネラーが、各乳化組成物0.5~0.6gを顔面に塗布した直後の「浸透感」及び塗布後10時間経過後の「潤いの持続性」について官能評価した。結果を、「良好である」と評価したパネラーの人数で示した。
実施例1~10と同様にして、表5~表9に示す組成の水中油型乳化組成物を製造し、X線による構造解析、残存水分量、浸透感及び潤いの持続感を評価した。結果を表5~表9に併せて示す。
表10に示す組成の水中油型乳化組成物について、製造方法(2)に従って製造し、得られた組成物について、それぞれ、X線による構造解析、残存水分量、皮膜形成性、浸透感及び潤いの持続性を評価した。結果を表10に併せて示す。
なお、実施例54~56と同様の組成で、製造方法(1)により製造されたもの(実施例30、3、5)を併せて示す。
第I相の成分(成分(A)~(E)を含む混合成分)を、80~95℃で加熱混合し、これに、プロペラ撹拌下(300rpm)、80~95℃に加熱した第II相(成分(F)を含む水相成分)を加えて乳化し、25℃まで徐々に冷却して、水中油型乳化組成物を得た。
実施例1~10と同様にして、表11に示す組成の水中油型乳化組成物(化粧水)を製造し、X線による構造解析を行い、皮膜形成性、浸透感及び潤いの持続性を評価した。結果を表11に併せて示す。
実施例1~10と同様にして、表12に示す組成の水中油型乳化組成物(乳液)を製造し、X線による構造解析を行い、皮膜形成性、浸透感及びうるおいの持続性を評価した。結果を表12に併せて示す。
実施例1~10と同様にして、表13に示す組成の水中油型乳化組成物(半透明ジェル)を製造し、X線による構造解析を行い、皮膜形成性、浸透感及びうるおいの持続性を評価した。結果を表13に併せて示す。
実施例1~10と同様にして、表14に示す組成の水中油型乳化組成物(クリーム)を製造し、X線による構造解析を行い、皮膜形成性、浸透感及びうるおいの持続性を評価した。結果を表14に併せて示す。
第I相の成分を、80~95℃で加熱混合し、これに、プロペラ撹拌下(300rpm)、80~95℃に加熱した第II相を加えて乳化し、25℃まで徐々に冷却した後、25℃の第III相を加え、表15に示す組成の水中油型乳化組成物(化粧水)を製造した。そして、X線による構造解析を行い、皮膜形成性、浸透感及び潤いの持続性を評価した。結果を表15に併せて示す。
第I相の成分を、80~95℃で加熱混合し、これに、プロペラ撹拌下(300rpm)、80~95℃に加熱した第II相を加えて乳化し、25℃まで徐々に冷却した後、25℃の第III相を加え、表16に示す組成の水中油型乳化組成物(化粧水)を製造した。そして、X線による構造解析を行い、皮膜形成性、浸透感及びうるおいの持続性を評価した。結果を表16に併せて示す。
実施例1~10と同様にして、表17に示す組成の水中油型乳化組成物(乳液)を製造し、X線による構造解析を行い、皮膜形成性、浸透感及びうるおいの持続性を評価した。結果を表17に併せて示す。
実施例1~10と同様にして、表18に示す組成の水中油型乳化組成物(クリーム)を製造し、X線による構造解析を行い、皮膜形成性、浸透感及びうるおいの持続性を評価した。結果を表18に併せて示す。
Claims (11)
- 次の成分(A)、(B)、(C)、(D)、(E)及び(F):
(A)水酸基を2個以上有する有機化合物であって、無機性値が220~450、有機性値が300~1000である有機化合物 0.001~10重量%、
(B)水酸基を1個有する有機化合物であって、無機性値が100~200、有機性値が280~700である有機化合物 0.001~10重量%、
(C)一般式(2):
(D)ポリオキシエチレン基を有するHLB10以上の非イオン界面活性剤、イオン性界面活性剤及びスフィンゴシン塩類から選ばれる1種以上の化合物 0.00012~10重量%、
(E)エリスリトール、トレイトール、キシリトール及びマンニトールから選ばれる糖アルコール、2単糖並びに3単糖から選ばれる1種以上の化合物 0.003~15重量%、
(F)水
を含有する乳化組成物。 - 成分(B)が、炭素数14~22の高級アルコール及びステロール類から選ばれる1種以上の化合物である請求項1又は2記載の乳化組成物。
- 成分(A)において、一般式(1)中のR、及び成分(B)において、高級アルコール中の炭化水素基が、直鎖炭化水素基である請求項2又は3記載の乳化組成物。
- 成分(D)が、アニオン界面活性剤又はスフィンゴシン塩類である請求項1~4記載のいずれか1項記載の乳化組成物。
- α-ゲル構造を形成する請求項1~5のいずれか1項記載の乳化組成物。
- ((A)+(B))/((A)+(B)+(C))が0.15以上で、かつ(A)/(A)+(B)が0.1以上である請求項1~6のいずれか1項記載の乳化組成物。
- (E)/((A)+(B)+(C))が0.01~5である請求項1~7のいずれか1項記載の乳化組成物。
- 成分(A)がモノベヘン酸グリセリル又はモノセチルグリセリルエーテル、
成分(B)がセタノール、
成分(C)が一般式(2)で表される化合物、
成分(D)がステアロイルグルタミン酸塩又はスフィンゴシン塩類、
成分(E)がキシリトール、
成分(F)が水
である請求項1~8のいずれか1項記載の乳化組成物。 - 成分(A)~(E)を含む混合成分と、成分(F)を含む水相成分を混合して乳化する請求項1~9のいずれか1項記載の乳化組成物の製造方法。
- 成分(A)~(D)を含む混合成分と、成分(E)及び(F)を含む水相成分を混合して乳化する請求項1~9のいずれか1項記載の乳化組成物の製造方法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010800305122A CN102724953A (zh) | 2009-07-06 | 2010-07-06 | 乳化组合物 |
EP10796902.4A EP2452668B1 (en) | 2009-07-06 | 2010-07-06 | Emulsified composition |
RU2012103897/04A RU2551853C2 (ru) | 2009-07-06 | 2010-07-06 | Эмульгированная композиция |
US13/382,298 US8647649B2 (en) | 2009-07-06 | 2010-07-06 | Emulsified composition |
US14/096,397 US20140100276A1 (en) | 2009-07-06 | 2013-12-04 | Emulsified composition |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009159738 | 2009-07-06 | ||
JP2009159737 | 2009-07-06 | ||
JP2009-159738 | 2009-07-06 | ||
JP2009-159737 | 2009-07-06 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/382,298 A-371-Of-International US8647649B2 (en) | 2009-07-06 | 2010-07-06 | Emulsified composition |
US14/096,397 Continuation US20140100276A1 (en) | 2009-07-06 | 2013-12-04 | Emulsified composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011004589A1 true WO2011004589A1 (ja) | 2011-01-13 |
Family
ID=43429020
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2010/004414 WO2011004589A1 (ja) | 2009-07-06 | 2010-07-06 | 乳化組成物 |
Country Status (5)
Country | Link |
---|---|
US (2) | US8647649B2 (ja) |
EP (1) | EP2452668B1 (ja) |
CN (1) | CN102724953A (ja) |
RU (1) | RU2551853C2 (ja) |
WO (1) | WO2011004589A1 (ja) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102949303A (zh) * | 2011-08-09 | 2013-03-06 | 花王株式会社 | 乳化组合物 |
WO2013180157A1 (ja) * | 2012-05-30 | 2013-12-05 | 花王株式会社 | 乳化化粧料組成物 |
JP2014108953A (ja) * | 2012-12-03 | 2014-06-12 | Kao Corp | 乳化化粧料 |
US20140194522A1 (en) * | 2011-08-09 | 2014-07-10 | Kao Corporation | Emulsion Composition |
JP2016084360A (ja) * | 2011-03-31 | 2016-05-19 | 花王株式会社 | ベシクル組成物 |
JP2016222586A (ja) * | 2015-05-29 | 2016-12-28 | 花王株式会社 | 頭皮用化粧料 |
JP2017124995A (ja) * | 2016-01-15 | 2017-07-20 | 株式会社ファンケル | ゲル状組成物 |
TWI618546B (zh) * | 2011-03-31 | 2018-03-21 | Kao Corp | Emulsified composition |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101917201B1 (ko) * | 2011-10-07 | 2018-11-09 | (주)아모레퍼시픽 | 고보습 세정제 조성물 |
JP6016728B2 (ja) * | 2013-08-02 | 2016-10-26 | 富士フイルム株式会社 | セラミド分散組成物 |
FR3011741B1 (fr) * | 2013-10-11 | 2015-10-23 | Oreal | Composition cosmetique de revetement des fibres keratiniques |
US9433567B2 (en) * | 2013-10-17 | 2016-09-06 | Kao Corporation | Skin cosmetic composition |
SG10202108834TA (en) | 2015-03-12 | 2021-09-29 | Givaudan Sa | Emulsions |
WO2017074896A1 (en) | 2015-10-29 | 2017-05-04 | Glaxosmithkline Consumer Healthcare Holdings (Us) Llc | Novel occlusive formulations |
US11337900B2 (en) * | 2015-10-29 | 2022-05-24 | Lg Household & Health Care Ltd. | Method of use and compositions |
SG11201803045WA (en) | 2015-10-29 | 2018-05-30 | Glaxosmithkline Consumer Healthcare Holdings Us Llc | Novel occlusive compositions |
FR3060327B1 (fr) | 2016-12-16 | 2020-02-21 | L'oreal | Emulsion h/e comprenant un alcool gras en c16-c30, un tensioactif anionique, une huile, une cire et un solvant hydrophile |
EP3558215A4 (en) | 2016-12-23 | 2020-08-05 | L'oreal | COMPOSITION WITH CRYSTALLINE PHASE |
CN117813078A (zh) | 2021-07-29 | 2024-04-02 | 莱雅公司 | 用于护理皮肤的组合物 |
WO2023038968A2 (en) * | 2021-09-09 | 2023-03-16 | The Trustees Of Indiana University | Compositions and methods to treat skin disorders |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003171229A (ja) * | 2001-12-10 | 2003-06-17 | Kao Corp | セラミド類乳化物の製造法 |
JP2007022997A (ja) | 2005-07-21 | 2007-02-01 | Kao Corp | 乳化組成物 |
JP2008127341A (ja) * | 2006-11-22 | 2008-06-05 | Nippon Fine Chem Co Ltd | シロキクラゲ由来水溶性多糖類の加水分解物、及びこれを含有する抗酸化剤並びに化粧料又は皮膚外用剤、食品 |
JP2008297301A (ja) * | 2007-05-01 | 2008-12-11 | Fancl Corp | セラミド溶液及び皮膚外用剤 |
JP2008308462A (ja) * | 2007-06-15 | 2008-12-25 | Kobayashi Pharmaceut Co Ltd | 皮膚外用組成物 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2712188B1 (fr) * | 1993-11-08 | 1996-01-26 | Oreal | Composition cosmétique destinée au maquillage de la peau, son procédé de préparation et produit de maquillage obtenu à partir de ladite composition. |
JP3299054B2 (ja) | 1994-10-19 | 2002-07-08 | 花王株式会社 | 皮膚化粧料 |
TW453881B (en) | 1995-10-16 | 2001-09-11 | Kao Corp | Cosmetic composition comprising amide derivatives |
JP3400666B2 (ja) | 1996-12-20 | 2003-04-28 | 高砂香料工業株式会社 | 皮膚保護剤 |
JP2000119178A (ja) | 1998-10-13 | 2000-04-25 | Shionogi & Co Ltd | セラミド含有組成物 |
JP3829049B2 (ja) | 1999-07-27 | 2006-10-04 | 株式会社資生堂 | 水中油型乳化組成物 |
JP4350269B2 (ja) | 2000-05-11 | 2009-10-21 | 高砂香料工業株式会社 | 化粧料添加用組成物 |
KR100439068B1 (ko) | 2001-09-07 | 2004-07-05 | 주식회사 코리아나화장품 | 레티놀을 3중으로 안정화한 화장료 |
CN1612722A (zh) * | 2001-11-13 | 2005-05-04 | 宝洁公司 | 包含用某种渗透保护剂稳定化的酶的组合物以及将这样的组合物用于个人护理的方法 |
JP4220698B2 (ja) | 2001-12-10 | 2009-02-04 | 花王株式会社 | 皮膚外用剤 |
EP1462081B1 (en) * | 2001-12-10 | 2012-08-08 | Kao Corporation | Production of ceramide emulsions |
US7169382B2 (en) | 2003-01-30 | 2007-01-30 | L'oreal | Reconstructed epidermis/skin equivalent comprising a ceramide 7 and /or 5.5 and lipid lamellar vesicular compositions comprising ceramide 7 and/or 5.5 compounds |
EP1443108A3 (fr) | 2003-01-30 | 2005-10-12 | L'oreal | Procédés de préparation d'un épiderme reconstruit supplémenté en céramide 7 ou 5.5, composition à base de vésicules lamellaires lipidiques incorporant un dérivé du céramide 7 et/ou 5.5 et son utilisation |
CN1761450B (zh) | 2003-02-13 | 2010-05-05 | 株式会社林原生物化学研究所 | 特征在于含有α,α-海藻糖的糖类衍生物的皮肤外用剂 |
JP4152301B2 (ja) | 2003-10-31 | 2008-09-17 | 株式会社資生堂 | 水中油型乳化組成物 |
JP2006056851A (ja) | 2004-08-23 | 2006-03-02 | Shu Uemura:Kk | 化粧料 |
JP4751142B2 (ja) | 2005-08-29 | 2011-08-17 | 花王株式会社 | 水中油型乳化化粧料 |
KR100650043B1 (ko) | 2006-01-31 | 2006-11-28 | (주)아모레퍼시픽 | 피부탄력 개선용 유화 조성물 |
JP4968774B2 (ja) | 2006-08-11 | 2012-07-04 | 株式会社 資生堂 | クリーム組成物 |
ATE468100T1 (de) | 2006-10-13 | 2010-06-15 | Evonik Goldschmidt Gmbh | Hautbehandlungszusammensetzung |
JP5214872B2 (ja) | 2006-11-13 | 2013-06-19 | 株式会社コーセー | ベシクル組成物及びそれを配合した皮膚外用剤 |
TW200904482A (en) * | 2007-03-29 | 2009-02-01 | Shaklee Corp | Compositions and methods for inhibiting melanogenesis |
CN101715457B (zh) * | 2007-04-24 | 2013-01-02 | 丘比株式会社 | 阳离子化透明质酸和/或其盐及其制法、及使用其的毛发改善剂、角质层修复剂、皮肤改善剂和化妆品 |
CN101674798B (zh) | 2007-04-26 | 2015-03-25 | 株式会社资生堂 | 水包油型乳化组合物及其制备方法 |
-
2010
- 2010-07-06 WO PCT/JP2010/004414 patent/WO2011004589A1/ja active Application Filing
- 2010-07-06 EP EP10796902.4A patent/EP2452668B1/en active Active
- 2010-07-06 CN CN2010800305122A patent/CN102724953A/zh active Pending
- 2010-07-06 US US13/382,298 patent/US8647649B2/en active Active
- 2010-07-06 RU RU2012103897/04A patent/RU2551853C2/ru not_active IP Right Cessation
-
2013
- 2013-12-04 US US14/096,397 patent/US20140100276A1/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003171229A (ja) * | 2001-12-10 | 2003-06-17 | Kao Corp | セラミド類乳化物の製造法 |
JP2007022997A (ja) | 2005-07-21 | 2007-02-01 | Kao Corp | 乳化組成物 |
JP2008127341A (ja) * | 2006-11-22 | 2008-06-05 | Nippon Fine Chem Co Ltd | シロキクラゲ由来水溶性多糖類の加水分解物、及びこれを含有する抗酸化剤並びに化粧料又は皮膚外用剤、食品 |
JP2008297301A (ja) * | 2007-05-01 | 2008-12-11 | Fancl Corp | セラミド溶液及び皮膚外用剤 |
JP2008308462A (ja) * | 2007-06-15 | 2008-12-25 | Kobayashi Pharmaceut Co Ltd | 皮膚外用組成物 |
Non-Patent Citations (5)
Title |
---|
ATSUSHI FUJITA: "Prediction of Organic Compounds by a Conceptual Diagram", KAGAKU-NO-RYOUIKI, vol. 11, no. 10, 1957, pages 719 - 725 |
J. LIPID RES., vol. 24, 1983, pages 759 |
J. LIPID. RES., vol. 35, 1994, pages 2069 |
See also references of EP2452668A1 |
WILSON, D. A.; OTT, E., J. CHEM. PHYS., vol. 2, 1934, pages 231 - 238 |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI618546B (zh) * | 2011-03-31 | 2018-03-21 | Kao Corp | Emulsified composition |
US9694076B2 (en) | 2011-03-31 | 2017-07-04 | Kao Corporation | Vesicle composition |
JP2016084360A (ja) * | 2011-03-31 | 2016-05-19 | 花王株式会社 | ベシクル組成物 |
CN102949303A (zh) * | 2011-08-09 | 2013-03-06 | 花王株式会社 | 乳化组合物 |
US9339448B2 (en) * | 2011-08-09 | 2016-05-17 | Kao Corporation | Emulsion composition |
US20140194522A1 (en) * | 2011-08-09 | 2014-07-10 | Kao Corporation | Emulsion Composition |
US9278059B2 (en) | 2012-05-30 | 2016-03-08 | Kao Corporation | Emulsified cosmetic composition |
JPWO2013180157A1 (ja) * | 2012-05-30 | 2016-01-21 | 花王株式会社 | 乳化化粧料組成物 |
JP5571258B2 (ja) * | 2012-05-30 | 2014-08-13 | 花王株式会社 | 乳化化粧料組成物 |
CN103445975A (zh) * | 2012-05-30 | 2013-12-18 | 花王株式会社 | 乳化化妆品组合物 |
CN103445975B (zh) * | 2012-05-30 | 2017-08-22 | 花王株式会社 | 乳化化妆品组合物 |
WO2013180157A1 (ja) * | 2012-05-30 | 2013-12-05 | 花王株式会社 | 乳化化粧料組成物 |
WO2014087955A1 (ja) * | 2012-12-03 | 2014-06-12 | 花王株式会社 | 乳化化粧料 |
JP2014108953A (ja) * | 2012-12-03 | 2014-06-12 | Kao Corp | 乳化化粧料 |
JP2016222586A (ja) * | 2015-05-29 | 2016-12-28 | 花王株式会社 | 頭皮用化粧料 |
JP2017124995A (ja) * | 2016-01-15 | 2017-07-20 | 株式会社ファンケル | ゲル状組成物 |
Also Published As
Publication number | Publication date |
---|---|
RU2012103897A (ru) | 2013-08-20 |
EP2452668A4 (en) | 2016-06-15 |
US20140100276A1 (en) | 2014-04-10 |
RU2551853C2 (ru) | 2015-05-27 |
US8647649B2 (en) | 2014-02-11 |
CN102724953A (zh) | 2012-10-10 |
US20120108661A1 (en) | 2012-05-03 |
EP2452668B1 (en) | 2018-10-03 |
EP2452668A1 (en) | 2012-05-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2011004589A1 (ja) | 乳化組成物 | |
JP4926420B2 (ja) | 乳化組成物 | |
JP5690516B2 (ja) | 乳化組成物 | |
JP5941732B2 (ja) | 乳化組成物 | |
US9278059B2 (en) | Emulsified cosmetic composition | |
TWI451877B (zh) | Emulsion composition | |
JP5517511B2 (ja) | 化粧料の製造法 | |
JP5917043B2 (ja) | 皮膚外用剤 | |
JP4751142B2 (ja) | 水中油型乳化化粧料 | |
JP5339813B2 (ja) | 逆ベシクル組成物 | |
JP6423701B2 (ja) | 化粧料 | |
JP5690517B2 (ja) | 乳化組成物 | |
JP7324278B2 (ja) | セラミド類とオレイン酸イソブチルを含有する組成物 | |
JP4284236B2 (ja) | 水中油型乳化化粧料 | |
US11896703B2 (en) | Liquid lipid composite composition for improving hair condition | |
JP4188150B2 (ja) | 皮膚外用剤 | |
JP6654812B2 (ja) | 乳化組成物 | |
JP7075955B2 (ja) | ベヘンジモニウムエチルリン酸ステアリルとアルキロイル乳酸塩とセラミド類を含有する組成物 | |
JP2017019754A (ja) | エラスターゼ阻害剤 | |
JP2020200283A (ja) | シート状化粧料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201080030512.2 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10796902 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010796902 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13382298 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012103897 Country of ref document: RU |