CN102727392A - Emulsified composition - Google Patents
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- CN102727392A CN102727392A CN2012100863242A CN201210086324A CN102727392A CN 102727392 A CN102727392 A CN 102727392A CN 2012100863242 A CN2012100863242 A CN 2012100863242A CN 201210086324 A CN201210086324 A CN 201210086324A CN 102727392 A CN102727392 A CN 102727392A
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Abstract
The invention relates to a manufacture method for an emulsified composition. The manufacture method comprises: a process 1 of mixing the following components (A), (B), (C), and (D) and an aqueous phase I comprising (F1), and then performing emulsifying and cooling; then, a process 2 of further mixing the following component (E) and an aqueous phase II comprising (F2), (a) 0.001-10 mass% of a compound represented by the following general formula (1), wherein Z1 is provided with a structure of more than two hydroxyl groups on residues of glycerol, water loss sorbitol, sorbitol or sucrose, Y1 is an ester bond or an ether bond, R is C14-22 alkyl, n is a number of 1-4; (B) 0.001-10 mass% of more than one compound selected from high alcohol with the carbon number of 14-22 and sterols; (C) 0.001-15 mass% of a compound represented by a general formula (2), R1 is C4-30 alkyl, Z is methylene, methyne or O, X2, and X3 are H, OH or an acetoxy group, X4 is H, acetyl, or glyceryl, r2 and R3 are H, OH, hydroxymethyl or acetoxy methyl, R4 is C5-60 alkyl, r5 is H, C1-30 alkyl; (D) 0.00025-10 mass% of a negative ion surfactant; (F1) water; (E) 0.001-6 mass% of a water-soluble polymer selected from an alkyl modified polyacrylic acid ethylene polymer and an alkyl modified polyose polymer; and (F2) water.
Description
Technical field
The present invention relates to emulsification composition.
Background technology
In the outermost horny layer of skin, there is the iuntercellular lipid that fills corneocyte and its gap.It is α-gel structure most, for skin, through suppress from the material of outside intrusion, by the water evaporates of inside the time, also keep the moisture of himself, thereby have the function of maintenance skin softness and slick outward appearance.
Usually, known because the minimizing of iuntercellular lipid, particularly ceramide can cause not preferred skin state, thus consider that the way of replenishing ceramide with external relates to the reduction that improves the skin function.
Yet, because ceramide high-melting-point and crystallinity are high, be difficult to be matched with in the external agent etc., thereby, carried out various discussions to stably cooperating ceramide.
For example, in patent documentation 1, put down in writing the crystallization that emulsification composition with specific ratio combination ceramide, fatty acid monoglyceride, higher alcohol can suppress ceramide and separated out, form the α-gel structure that keeps moisture easily, thereby moistening effect has been high.
In addition, also inquired into, thereby can further improve the moisture hold facility of α-gel, the state (patent documentation 2, patent documentation 3) that moisture is residued in for a long time improve skin on the skin through further specific sugar alcohol or 2 monosaccharide or 3 monosaccharide of combination.
Yet, though these compositionss form α-gel structure, owing to be difficult to coat on the skin with low viscosity; Thereby even formed the epithelium with moistening effect, its epithelium is more crisp; Can not cover skin equably, thereby also be difficult to bring into play sufficient moisture hold facility.
In addition, because epithelium shortcoming flexibility and elasticity so coating back skin has the rough sense of distinctive harsh feeling, thereby can not get good use sense of touch.In addition, also has the problem that coating back outward appearance shortcoming is smooth, outward appearance that can not get skin improves effect.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2007-22997 communique
Patent documentation 2: TOHKEMY 2011-32265 communique
Patent documentation 3: TOHKEMY 2011-32266 communique
Summary of the invention
The present invention provides a kind of manufacturing approach of emulsification composition, and said manufacturing approach has: following composition (A), (B), (C), (D) and the water I that contains (F1) are mixed, then emulsifying and refrigerative operation 1; Then, composition (E) below further mixing and the operation 2 that contains the water II of (F2),
(A) chemical compound 0.001～10 quality % that representes by following general formula (1),
(in the formula, Z
1Be illustrated in the structure that has the hydroxyl more than 2 on glycerol, anhydrosorbitol, Sorbitol or the sucrose residue, Y
1Expression ester bond or ehter bond, R representes that carbon number is 14～22 alkyl, n representes 1～4 number.)
(B) being selected from carbon number is 14～22 higher alcohol and 0.001～10 quality % of the chemical compound more than a kind in the sterols;
(C) chemical compound 0.001～15 quality % that representes by general formula (2);
(in the formula, R
1Expression is 4～30 straight chain, side chain or cyclic saturated or unsaturated alkyl by hydroxyl, carbonyl or amino replacement or not substituted carbon number; Z representes methylene, methine or oxygen atom; X
1, X
2And X
3Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently; X
4Represent hydrogen atom, acetyl group or glyceryl, or form oxo group (still, X when Z is methine with adjacent oxygen atom
1And X
2Any one for hydrogen atom another does not exist, work as X
4X when forming oxo group
3Do not exist.); R
2And R
3Represent hydrogen atom, hydroxyl, methylol or acetyl-o-methyl respectively independently; R
4Expression replaced by hydroxyl, carbonyl or amino or not substituted main chain on had or do not had ehter bond, ester bond or an amido link carbon number be 5～60 straight chain, side chain or cyclic saturated or undersaturated alkyl; R
5The expression hydrogen atom, or expression has or does not have the saturated or undersaturated alkyl that the substituent total carbon atom number that is selected from hydroxyl, hydroxy alkoxy base, alkoxyl and the acetoxyl group is 1～30 straight or branched; Dotted portion representes it can is unsaturated bond.)
(D) anion surfactant 0.00025～10 quality %;
(F1) water;
(E) be selected from water soluble polymer 0.001～6 quality % in alkyl-modified polyacrylic polyvinyl and the alkyl-modified polysaccharide polymer;
(F2) water.
In addition, the present invention provides a kind of emulsification composition, and it contains following composition (A), (B), (C), (D), (E) and (F),
(A) single Compritol 888 ATO or single cetyl glycerin ether 0.001～10 quality %;
(B) hexadecanol or stearyl alcohol 0.001～10 quality %;
(C) ceramide type 0.001～15 quality % that representes by general formula (3) or general formula (4),
(in the formula, R
11Expression is 7～19 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl replacement or not substituted carbon number; Z
1Expression methylene or methine; X
5, X
6And X
7Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently; X
8The expression hydrogen atom, or form oxo group with adjacent oxygen atom and (still, work as Z
1During for methine, X
5And X
6Any one for hydrogen atom another does not exist; Work as X
8When forming oxo group, X
7Do not exist.); R
12Expression methylol or acetyl-o-methyl; R
13The expression hydrogen atom, or the expression carbon number is 1～4 alkyl; R
14Expression is replaced by hydroxyl or not substituted carbon number is 5～30 straight chain, side chain or cyclic saturated or undersaturated alkyl, or is illustrated on the ω end of this alkyl with ester bond and combines to be replaced or not substituted carbon number is the group that the saturated or undersaturated fatty acid of 8～22 straight or branched forms by hydroxyl; Dotted portion representes it can is unsaturated bond.)
(in the formula, R
15Expression is 10～22 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl replacement or not substituted carbon number; X
9Expression hydrogen atom, acetyl group or glyceryl; R
16Expression is replaced by hydroxyl or amino or not substituted carbon number is 5～22 straight chain, side chain or cyclic saturated or undersaturated alkyl, or is illustrated on the ω end of this alkyl with ester bond and combines to be replaced or not substituted carbon number is the group that the saturated or undersaturated fatty acid of 8～22 straight or branched forms by hydroxyl; R
17The expression hydrogen atom, or expression is 1～30 alkyl by hydroxyl, hydroxy alkoxy base, alkoxyl or acetoxyl group replacement or not substituted total carbon atom number.)
(D) stearyl glutamate, Glu, stearyl methyl tauride or polyoxyethylene stearyl base ether phosphate 0.00025～10 quality %;
(E) (acrylic acid/alkyl acrylate (C10-30)) copolymer, (alkyl acrylate/methacrylic acid stearyl alcohol polyethers-20) copolymer, laureth-13PG hydroxyethyl-cellulose or stearic oxygen base PG hydroxyethyl-cellulose sodium sulfonate 0.001～6 quality %;
(F) water.
The effect of invention
Emulsification composition of the present invention is owing to can access high viscosity and elastic fluidity, and coated film has flexibility and elasticity, thereby cover skin equably, improves the moisture hold facility, and makes the skin sense of touch smooth, and outward appearance is also smooth.
The specific embodiment
The present invention relates to a kind of emulsification composition, its coated film has flexibility and elasticity, and cover skin improves the moisture hold facility, and makes the skin sense of touch smooth equably, and outward appearance is also smooth.
Present inventors find that the α-gel that designs for improving the moisture hold facility is through making up specific water soluble polymer; Can obtain owing to can obtain high viscosity and elastic fluidity; Coated film has flexibility and elasticity, thereby cover skin equably, improves the moisture hold facility; And can make the skin sense of touch smooth, the also slick emulsification composition of outward appearance.
The composition that uses among the present invention (A) is the chemical compound by above-mentioned general formula (1) expression.
In the formula, be 14～22 alkyl, be preferably straight-chain alkyl, for example can enumerate straight chained alkyls such as myristyl, palmityl, stearyl, mountain Yu base as the carbon number of representing by R; Palmityl, oil base etc.
As chemical compound, can enumerate fatty acid monoglyceride, anhydrosorbitol mono fatty acid ester, anhydrosorbitol di fatty acid ester, Sorbitol mono fatty acid ester, Sorbitol di fatty acid ester, sucrose monofatty acid ester, glycerol monoalkyl ether etc. by general formula (1) expression.
As composition (A), preferably glycerine mono fatty acid ester, anhydrosorbitol mono fatty acid ester, glycerol monoalkyl ether.Wherein, Preferred monopalmitin, glyceryl monostearate, single Compritol 888 ATO, anhydrosorbitol monostearate, single cetyl glycerin ether, single stearyl glycerin ether; In addition; After improving, state the formation property of sheet epithelium, the viewpoint of water-retaining property, more preferably single Compritol 888 ATO or single cetyl glycerin ether.
Composition (A) can use the chemical compound more than a kind, in all forming, is containing 0.001～10 quality %, preferably contains 0.05～7 quality %, more preferably contains 0.25～3 quality %.If in this scope, then coat emulsification composition of the present invention on the skin after, the lipid layer that the composition that can in dry run, after skin surface forms, state (B)～(E) constitutes and water stratification be the sheet epithelium of arrangement alternately.Because it is this result has improved the moisture hold facility that can be used for keeping interlayer moisture, therefore preferred.Also, therefore preferred because the use sense of touch of coated film also becomes well.
In composition used in the present invention (B), higher alcohol is that carbon number is 14～22, preferably carbon number is 16～18 higher alcohol.For example, can enumerate myristyl alcohol, hexadecanol, stearyl alcohol, behenyl alcohol etc.
Wherein, preferred hexadecanol, stearyl alcohol, more preferably hexadecanol.
In addition, in composition (B),, can enumerate cholesterol, plant sterol as sterol.Plant sterol is the general name of plant sterols such as cupreol, campesterol, stigmasterol, brassicasterol, and its composition is unqualified.
Composition (B) can use more than a kind, in all forming, is containing 0.001～10 quality %, preferably contains 0.05～7 quality %, more preferably contains 0.1～3 quality %.If in scope, then emulsification composition of the present invention is coated skin after, can be in dry run skin surface form mentioned component (A) and after state the alternately sheet epithelium of arrangement of lipid layer that composition (C)～(E) constitutes and water stratification.Because it is this result has improved the moisture occlusive that can keep interlayer moisture, therefore preferred.Also, therefore preferred because also improved the outward appearance of skin after the coating.
The ceramide type of the composition that uses among the present invention (C) is the chemical compound with above-mentioned general formula (2) expression.
In the formula, R
1Being to be 4～30 by hydroxyl, carbonyl or amino substituted carbon number, to be preferably can be 7～22 straight chain, side chain or cyclic saturated or undersaturated alkyl or hydrogen atom by the substituted carbon number of hydroxyl.
Z representes any one in methylene, methine or the oxygen atom.
X
1, X
2And X
3Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently.Preferred X
1, X
2And X
3In 0～1 be hydroxyl, remaining is oxygen atom.When Z is methine, X
1And X
2Any one be merely hydrogen atom, and another does not exist.In addition, X
4Be preferably hydrogen atom or glyceryl.
R
2And R
3Expression hydrogen atom, hydroxyl, methylol or acetyl-o-methyl, preferred R
2Be hydrogen atom or methylol, preferred R
3Be hydrogen atom.
R
4Expression can be 5～60 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl, carboxyl or carbon number amino substituted and that can on main chain, have ehter bond, ester bond or an amido link.Preferably can enumerate; Can be 5～35 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl or amino substituted carbon number, or on the ω position of this alkyl, to combine with ester bond or combine with amido link by the substituted carbon number of hydroxyl the group of 8～22 straight chain, side chain or cyclic saturated or undersaturated fatty acid.As bonded fatty acid, preferred isostearic acid, 12-hydroxy stearic acid or linoleic acid.
R
5The expression hydrogen atom, or also can have the saturated or undersaturated alkyl that the substituent total carbon atom number that is selected from hydroxyl, hydroxy alkoxy base, alkoxyl and acetoxyl group is 1～30 straight or branched.Work as R
1For hydrogen atom, when Z is oxygen atom, R
5It for total carbon atom number 10～30 alkyl.In addition, work as R
1During for alkyl, R
5It for total carbon atom number 1～8 alkyl.Wherein, preferred hydrogen atom or also can be selected from 1～3 substituted total carbon atom number in hydroxyl and hydroxy alkoxy base, the alkoxyl be 1～8 alkyl.At this, as hydroxy alkoxy base and alkoxyl, preferred carbon number is 1～7 group.
As chemical compound by general formula (2) expression, the ceramide type of preferably representing by following general formula (3) or (4).
(I) chemical compound by general formula (3) expression can be from the natural ceramide type or the synthetic of same structure.
(in the formula, R
11Expression can be 7～19 straight chain, side chain or cyclic saturated or undersaturated alkyl by the substituted carbon number of hydroxyl; Z
1Expression methylene or methine; X
5, X
6And X
7Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently; X
8The expression hydrogen atom, or form oxo group with adjacent oxygen atom and (still, work as Z
1During for methine, X
5And X
6Any one for hydrogen atom another does not exist; Work as X
8When forming oxo group, X
7Do not exist.); R
12Expression methylol or acetyl-o-methyl; R
13The expression hydrogen atom, or the expression carbon number is 1～4 alkyl; R
14Expression can be 5～30 straight chain, side chain or cyclic saturated or undersaturated alkyl by the substituted carbon number of hydroxyl, or is illustrated on the ω end of this alkyl that to combine with ester bond to be the group that the saturated or undersaturated fatty acid of 8～22 straight or branched forms by the substituted carbon number of hydroxyl; Dotted portion representes it can is unsaturated bond.)
Preferably can enumerate R
11For carbon number is 7～19, more preferably carbon number is 13～15 straight chained alkyl, R
14For can being 9～27 straight chained alkyl or to combine linoleic carbon number with ester bond be the chemical compound of 9～27 straight chained alkyl by the substituted carbon number of hydroxyl.In addition, preferred X
8Represent hydrogen atom, or form oxo group with oxygen atom.In addition, as R
14, combine linoleic nonacosyl with ester bond on preferred tricosyl, 1-hydroxyl pentadecyl, 1-hydroxyl tricosyl, heptadecyl, 1-hydroxyl undecyl, the ω position.
Object lesson as the natural type ceramide; Can enumerate sphingol, dihydrosphingosine, phytosphingosine or sheath ammonia dienol (Sphingadienine) by amidatioon ceramide type 1～7 (for example; J.Lipid Res.; Fig. 2 and the J.Lipid.Res. of 24:759 (1983), the pig of Fig. 4 record of 35:2069 (1994) and people's ceramide type).
Further, the N-alkyl body (for example, N-methyl body) that also comprises these.
These ceramide types can use the optically active body of natural type (D (-) body), also can use the optically active body of non-natural type (L (+) body), can also use the mixture of natural type and non-natural type.The relative configuration of above-claimed cpd can be the configuration of natural type, also can be the configuration of non-natural type in addition, in addition, also can be these mixture.Wherein, the chemical compound of preferred CERAMIDE 1, CERAMIDE2, CERAMIDE3, CERAMIDE5, CERAMIDE6II (above, INCI, the 8th edition) and the material that is expressed from the next.
These can be from any one of natural extract and synthetic, can use commercially available product.
Commercially available article as such natural type ceramide; Can enumerate Ceramide I, CeramideIII, CeramideIIIA, CeramideIIIB, CeramideIIIC, CeramideVI (more than, Cosmo Farm company), Ceramide TIC-001 (high sand spice company), CERAMIDE II (Quest International company), DS-CeramideVI, DS-CLA-Phytoceramide, C6-Phytoceramide, DS-ceramide Y3S (DOOSAN company), CERAMIDE 2 (Sederma company).
(II) coagulating by general formula (4) expression like type ceramide (pseudo-ceramide).
(in the formula, R
15Expression can be 10～22 straight chain, side chain or cyclic saturated or undersaturated alkyl or hydrogen atom by the substituted carbon number of hydroxyl; X
9Expression hydrogen atom, acetyl group or glyceryl; R
16Expression can be 5～22 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl or amino substituted carbon number, or is illustrated on the ω end of this alkyl that to combine with ester bond to be the group that the saturated or undersaturated fatty acid of 8～22 straight or branched forms by the substituted carbon number of hydroxyl; R
17The expression hydrogen atom, or expression can be 1～30 alkyl by hydroxyl, hydroxy alkoxy base, alkoxyl or the substituted total carbon atom number of acetoxyl group.)
As R
16, combine on linoleic undecyl, the ω position to combine on linoleic pentadecyl, the ω position to combine on the pentadecyl, ω position of 12-hydroxy stearic acid to combine the undecyl of methyl branch isostearic acid on preferred nonyl, tridecyl, pentadecyl, the ω position with amido link with ester bond with ester bond with ester bond.
At R
15Under the situation for hydrogen atom, R
17Being preferably to be 10～30 by hydroxyl, hydroxy alkoxy base, alkoxyl or the substituted total carbon atom number of acetoxyl group, preferably total carbon atom number is 12～20 alkyl; At R
15For can being under the situation of 10～22 straight chain, side chain or cyclic saturated or undersaturated alkyl by the substituted carbon number of hydroxyl, R
17Preferred expression hydrogen atom, or expression can be 1～8 alkyl by hydroxyl, hydroxy alkoxy base, alkoxyl or the substituted total carbon atom number of acetoxyl group.As R
17Hydroxy alkoxy base or alkoxyl, preferred carbon number is 1～7.
As general formula (4), preferred R
15Be cetyl, X
9Be hydrogen atom, R
16Be pentadecyl, R
17Chemical compound for ethoxy; R
15Be cetyl, X
9Be hydrogen atom, R
16Be nonyl, R
17Chemical compound for ethoxy; Or R
15Be cetyl, X
9Be glyceryl, R
16Be tridecyl, R
17Be coagulating of 3-methoxy-propyl like type ceramide type, the more preferably R of general formula (4)
15Be cetyl, X
9Be hydrogen atom, R
16Be pentadecyl, R
17Chemical compound (N-(hexadecane oxygen base hydroxypropyl)-N-ethoxy palmitamide) for ethoxy.
The chemical compound of composition (C) can use more than a kind, in all forming, is containing 0.001～15 quality %, preferably contains 0.05～7 quality %, more preferably contains 0.5～5 quality %.If in scope; After then coating emulsification composition of the present invention on the skin, in dry run can skin surface form mentioned component (A), (B) and after state the alternately sheet epithelium of arrangement of lipid layer that composition (D)～(E) constitutes and water stratification.This result can keep interlayer moisture.In addition, in emulsification composition of the present invention and in the sheet epithelium of coating dry back formation, composition (C) does not have crystallization.Height permeates in skin because this result can make composition (C), and is therefore preferred.And then, improve the raising of use sense of touch because relate to coating back skin outward appearance, therefore preferred.
As the anion surfactant of the composition that uses among the present invention (D), for example can enumerate carbon numbers such as sodium laurate, potassium palmitate, sterin propylhomoserin and be 12～24 soap; Alkyl sulfate such as sodium lauryl sulfate, lauryl potassium sulfate salt; Alkyl ether sulphate salts such as polyoxyethylene lauryl sulfate ester triethanolamine; N-acyl sarcosinates such as sodium N-lauroyl sarcosinate; N-stearyl-N methyl taurine sodium, N-myristoyl-fatty acid amide sulfonates such as N methyl taurine sodium; Alkylphosphonics such as single stearyl sodium phosphate; Polyoxyethylene alkyl ether phosphate such as polyoxyethylene oleyl ether sodium phosphate, polyoxyethylene stearyl base ether phosphoric acid sodium; Long-chain sulfosuccinates such as two-2-ethylhexyl sodium sulfosuccinate; Long-chain N-acyl glutamates such as N-lauroyl glutamate list sodium, N-stearyl-L-sodium glutamate, N-stearyl-L-arginine glutamate, N-stearyl sodium glutamate, N-myristoyl-L-sodium glutamate etc.
Wherein, preferred carbon number is 12～24 soap, alkyl fatty esters salt, alkyl ether sulphate salts, fatty acid amide sulfonate, alkylphosphonic, polyoxyethylene alkyl ether phosphate, long-chain N-acyl glutamate.
Wherein, preferred stearyl glutamate, Glu, stearyl methyl tauride, polyoxyethylene stearyl base ether phosphate, further preferred stearyl glutamate, Glu, stearyl methyl tauride, more preferably stearyl glutamate, Glu.
As the salt of composition (D), be preferably selected from sodium salt, potassium salt, alkaline amino acid salt, the ammonium more than a kind, from the viewpoint of the viscosity that shows emulsification composition, be preferably selected from sodium salt, the arginine salt more than a kind.
Composition (D) can be used as acid and cooperates, and also can contain as salt with the alkali neutralization.In under this situation and the alkali of composition (D) be preferably selected from basic amino acid, sodium hydroxide, potassium hydroxide, triethanolamine, the calcium hydroxide more than a kind or 2 kinds, basic amino acid be preferably selected from arginine, lysine, the histidine more than a kind or 2 kinds.As in and the alkali of composition (D), the viewpoint from the viscosity of performance emulsification composition is preferably selected from a kind or 2 kinds in arginine, the sodium hydroxide, from the viewpoint of usability, more preferably arginine.
Composition (D) can use more than a kind, in all forming, is containing 0.00025～10 quality %, preferably contains 0.05～2 quality %, more preferably contains 0.1～1 quality %.If in this scope, then can emulsified component (A)～(C).In addition, emulsification composition of the present invention coated skin after, can be in dry run form the alternately sheet epithelium of arrangement of lipid layer that composition (A)～(D) and composition (E) constitute and water stratification at skin surface.This result is because can keep interlayer moisture, and is useful to improving the moisture hold facility, so preferred.
The composition that uses among the present invention (E) is the water soluble polymer that is selected from alkyl-modified polyacrylic polymer and the alkyl-modified polysaccharide polymer.
For example, can enumerate alkyl acrylate copolymer, (methyl) acrylic acid/(methyl) alkyl acrylate copolymer, alkyl acrylate alkyl methacrylate polyoxyethylene stearyl base ether copolymer, polysaccharide derivates etc.
More particularly, preferred (acrylic acid/alkyl acrylate (C10-30)) copolymer, (alkyl acrylate/methacrylic acid stearyl alcohol polyethers-20) copolymer, laureth-13PG hydroxyethyl-cellulose, stearic oxygen base PG hydroxyethyl-cellulose sodium sulfonate etc.
As commercially available article, for example,, can enumerate ACULYN33 (The Dow Chemical Company) as the acrylic acid alkyl ester polymer; As (methyl) acrylic acid/(methyl) alkyl acrylate copolymer, can enumerate PEMULEN TR-1, PEMULEN TR-2, Carbopol ETD2020 (more than, Lubrizol Advanced Materials, Inc.) etc.In addition, as alkyl acrylate alkyl methacrylate polyoxyethylene stearyl base ether copolymer, can enumerate ACULYN 22 (The Dow Chemical Company) etc.As polysaccharide derivates, can enumerate SPS-S-SA, SOFCARE EP-S (more than, KAO. Corp. SA), Natrosol Plus (Hercules-Aqualon) etc.
Composition (E) can use more than a kind, in all forming, is containing 0.001～6 quality %, preferably contains 0.05～5 quality %, more preferably contains 0.1～3 quality %.If in this scope, then can improve the storage stability of emulsification composition of the present invention.The crystallization of the lipid mixture that in addition, can suppress to constitute by composition (A)～(D).Its result after coating emulsification composition of the present invention, can give the sheet epithelium that is formed at skin surface flexibility in dry run.Because its result uses sense of touch/coating back raising skin outward appearance useful, therefore preferred to moisture hold facility/raising.
In the present invention, the water of composition (F) can be used as the surplus of each composition, in all forming, preferably contains 49～85 quality %, more preferably contains 55～80 quality %.
In the present invention; From obtaining the viewpoint of high viscosity and elastic fluidity; Composition (A), (B), (C), (D) and mass ratio (E) are preferably, (E)/((A)+(B)+(C))=0.0025～50, more preferably 0.01～3, be preferably 0.1～1.5 especially.Its result is on coating skin the time, can feel high coating sense, give good usability.
In addition, in order to obtain having flexibility and elastic epithelium, preferred (E)/(D)=0.025～100, more preferably 0.14～7.5, be preferably 1.2～6 especially.
In the present invention, more preferably make up the preferred separately composition and the preferred content of mentioned component.
In addition; In emulsification composition of the present invention; Preferably: composition (A) is single Compritol 888 ATO or single cetyl glycerin ether; Composition (B) is hexadecanol or stearyl alcohol, and composition (C) is that composition (D) is stearyl glutamate, Glu, stearyl methyl tauride or polyoxyethylene stearyl base ether phosphate by the chemical compound of general formula (1) expression; Composition (E) is (acrylic acid/alkyl acrylate (C10-30)) copolymer, (alkyl acrylate/methacrylic acid stearyl alcohol polyethers-20) copolymer, laureth-13PG hydroxyethyl-cellulose or stearic oxygen base PG hydroxyethyl-cellulose sodium sulfonate, and composition (F) is a water.
In addition; In emulsification composition of the present invention, preferred: composition (A) is single Compritol 888 ATO, and composition (B) is a hexadecanol; Composition (C) is the chemical compound by general formula (1) expression; Composition (D) is the stearyl glutamate, Glu, and composition (E) is (acrylic acid/alkyl acrylate (C10-30)) copolymer, (alkyl acrylate/methacrylic acid stearyl alcohol polyethers-20) copolymer, laureth-13PG hydroxyethyl-cellulose or stearic oxygen base PG hydroxyethyl-cellulose sodium sulfonate, and composition (F) is a water.
In the present invention, form the lipid of emulsion by composition (A)～(D).If these are carried out drying, then can cause crystallization, form hard and crisp epithelium, thereby can not obtain the high epithelium of moisture retention.Yet, through further containing composition (E), can suppress the crystallization of lipid, thereby contain moisture in a large number, form the alternately softish epithelium of the sheet of arrangement of lipid layer and water layer.Particularly,, then can increase the flexibility of epithelium, improve outward appearance and sense of touch smooth of skin if use hexadecanol to be composition (B).And then, can be provided for making the emulsification composition of the present invention of skin smears purposes, be used to make the moisture of skin retention agent emulsification composition of the present invention purposes and be used to make the purposes that the coated film of skin is formed the emulsification composition of the present invention of agent.
Emulsification composition of the present invention can also contain composition (B) and (C) in addition oiliness composition.For example, can enumerate hydrocarbon ils such as liquid paraffin, squalane, vaseline; Ether oils such as cetyl dimethylbutyl ether, ethylene glycol bisthioglycolate Octyl Ether, glyceryl list oleyl ether; Myristic acid stearyl, isopropyl palmitate, butyl stearate, di-2-ethylhexyl adipate, two capric acid DOPCPs, tricaprylin ester oils such as (trioctanoin); Higher fatty acids such as stearic acid, mountain Yu acid, different myristic acid; Fructus Canarii albi wet goods vegetable oil; Silicone oil such as dimethyl polysiloxane, cyclic dimethyl polysiloxane, methyl phenyl silicone, amino modified silicone, carboxy-modified silicone, pure modified silicone, alkyl-modified silicone, polyether modified silicone, fluorine modified silicone; Fluorine class wet goods such as perfluor alkyl ethide phosphoric acid, the acid of perfluoroalkyl polyoxy vincofos, PFPE, politef.These oiliness compositions preferably contain 0～20 quality % in all forming.
In addition, emulsification composition of the present invention can contain effective ingredient and the additive that uses in the common cosmetics, for example water-soluble vitamins such as ascorbic acid, nicotinamide, nicotinic acid; Animals and plants extracting solution such as Cortex Phellodendri extract, Radix Glycyrrhizae extract, Aloe extract, Herba Equiseti Arvinsis extract, tea extract, Fructus Cucumidis sativi extract, Flos Caryophylli extract, Radix Dauci Sativae extract, Radix Hamamelidis Mollis extracting solution, intacellin, Sargassum extract, Aesculus chinensis Bunge extract, grapefruit abstract, Thujopsis dolabrata extract, Lac regis apis extract, eucalyptus extracts, Thujopsis dolabrata extracting solution; Alkali such as potassium hydroxide, sodium hydroxide, triethanolamine, sodium carbonate; Acid such as citric acid, tartaric acid, lactic acid, phosphoric acid, succinic acid, adipic acid etc.
The manufacturing approach of emulsification composition of the present invention preferably has: composition (A)～(D) and the water I that contains the part (F1) of composition (F) are mixed, then emulsifying and refrigerative operation 1; Then, the further blending constituent (E) and the operation of water-phase component (water II) that contains the remainder (F2) of composition (F).Because according to this method, through after forming α-gel structure, making interpolymer interaction, thereby can obtain, so preferably at the excellent emulsion of wider temperature range internal stability.
Operation 1 is the operation that α-gel structure is formed, and is preferably selected from the operation in 4 manufacturing processes of following operation 1A, 1B, 1C and 1D.From the viewpoint of the property made, preferably unneutralized composition (D) is come the operation selected operation 1A and the operation 1C of neutral operation with alkali from possessing; From the viewpoint of apparent viscosity, the operation of preferably from the operation 1A of blending constituent oil phase (D) and operation 1B, selecting.As stated, operation 1 preferably possesses the operation of from operation 1A, operation 1B and operation 1C, selecting, and more preferably possesses operation 1A or operation 1B, further preferably possesses operation 1A.
Operation 1A: be operation with blending constituent of the oil phase that obtains containing composition (A), (B), (C) and unneutralized composition (D); Contain the part (F1) of composition (F) and the water I of alkali with in this oil phase, mixing, then emulsifying and refrigerative operation.
Operation 1B: be the operation of blending constituent with oil phase of the salt that obtains containing composition (A), (B), (C) and composition (D); With the water I that in this oil phase, mixes a part (F1) that contains composition (F), then emulsifying and refrigerative operation.
Operation 1C: be operation with the blending constituent that obtains containing composition (A), (B) and oil phase (C); Contain the part (F1) of unneutralized composition (D), composition (F) and the water I of alkali with in this oil phase, mixing, then emulsifying and refrigerative operation.
Operation 1D: be operation with the blending constituent that obtains containing composition (A), (B) and oil phase (C); With the water I of a part (F1) of in this oil phase, mixing the salt contain composition (D) and composition (F), then emulsifying and refrigerative operation.
In these methods, the moisture of composition (F) for (F1) and (F2) is added mixing, its mass ratio is preferably (F1)/(F2)=0.1～9, more preferably 0.25～4.
The emulsification composition that obtains is α-gel (crystallization of α type), suppresses separating out of crystallization (crystallization of γ type).α-gel can carry out structural analysis through X ray and confirm.α type structure is characterised in that, is hexagonal crystal system, and lipophilic group is vertical orientated with respect to the hydrophilic group aspect, occurs a sharp-pointed diffraction maximum near 21～23 ° at the Bragg angle.
In addition, the viscosity of emulsification composition under 25 ℃ is preferably 10～8000dPas, further is preferably 500～1500dPas, 1500～5000dPas more preferably.Emulsification composition of the present invention can obtain high viscosity and elastic fluidity like this through the combination mentioned component.
In addition, in the present invention, viscosity records through B8R type rotating cylinder viscometer (rotor C or D, 5r/min, mensuration 1 minute) down at 25 ℃.
In addition, the emulsification composition that obtains is an O/W emulsion composition, preferably as for example cosmetics or skin preparations for extenal use such as astringent, emulsion, butterfat, gel.About above-mentioned embodiment, method for using, the purposes of the emulsification composition below the present invention is further open.
Contain composition (A), (B), (C), (D), (E) and emulsification composition (F) and be used for making the purposes that the coated film of skin is formed agent.
Contain composition (A), (B), (C), (D), (E) and emulsification composition (F) in the purposes that is used for making skin preparations for extenal use.
Contain composition (A), (B), (C), (D), (E) and coated film formation (F) and use O/W emulsion composition skin.
Embodiment
Embodiment 1～10 and comparative example 1～7
Make the O/W emulsion composition of forming shown in table 1 and the table 2, when carrying out the mensuration of viscosity and remnant of moisture content, to epithelium, the observation of carrying out the affirmation of lamellar structure and carrying out apparent condition through SEM through SAXS.In addition, the sense of touch and the outward appearance of the skin after the moistening persistence of sensory evaluation, the coating.The result is shown in table 1 and the table 2 in the lump.
(manufacturing approach)
Composition heating with the I phase under 80～90 ℃ mixes; (300rpm) is heated to the composition of 80～90 ℃ II phase therein under propeller agitation; Apply shearing with emulsifying homogenizer (homo mixer) on one side with 7000rpm, 10 minutes condition; Carry out emulsifying on one side, form α-gel.Slowly be cooled to after 25 ℃, add the composition of III phase, obtain O/W emulsion composition.
(evaluation methodology)
(1) viscosity:
Under 25 ℃, measure through B8R type rotating cylinder viscometer (rotor C or D, 5r/min, mensuration 1 minute).
(2) remnant of moisture content:
In the metal tray of 6 * 6cm, expand the 1g O/W emulsion composition equably, under 20 ℃, the constant temperature and humidity of humidity 40%, to mass change mapping with respect to the time with certain thickness.Since through the time form the lamella epithelium, mass change becomes minimum thereafter.Try to achieve the remnant of moisture content of quality after certain 24 hours, try to achieve in the preparation water quantities with respect to solid constituent with following formula.The whole compositions that in solid constituent, contain composition (A)～(E).
(3) affirmation of the lamellar structure through SAXS:
Go up with 0.001g/cm at dermatine PRARE (registered trade mark)
2Sprawl O/W emulsion composition equably, make it dry 1 day after, with Nano-viewer,
The state on epithelium surface is measured in irradiation in 30 minutes in photographing unit length (camera length) 649.5mm, 2 θ=0.2～5 ° scope.
(4) observation of the epithelium apparent condition through SEM:
Go up with 0.001g/cm at dermatine PRARE (registered trade mark)
2Sprawl O/W emulsion composition equably, make it drying after 1 day, observe the state on epithelium surface through SEM (scanning electron microscope) with 50 times of multiplying powers.The result is represented by following benchmark.
Zero: the boundary member of skin mound sulci of skin is smooth.
△: the boundary member of skin mound sulci of skin has crispaturas.
*: do not form epithelium.
(5) sense of touch (smooth) and the outward appearance (smooth in appearance) of the skin after moistening persistence, the coating:
Sensory evaluation at once " sense of touch of skin is smooth " and " smooth in appearance of skin ", coating warp sensory evaluation again " moistening persistence " later in 10 hours after 12 special evaluation group members coat each O/W emulsion composition of 0.4～0.6g on the face.Number with the special evaluation group member who is evaluated as " well " is come ecbatic.
Embodiment 11～29 and comparative example 8～9
Likewise make shown in table 3～table 6 O/W emulsion composition of forming with embodiment 1～10, when carrying out the mensuration of viscosity and remnant of moisture content, the observation that epithelium is carried out the affirmation of lamellar structure through SAXS and carries out apparent condition through SEM.In addition, estimate the sense of touch and the outward appearance of the skin after moistening persistence, the coating.The result is shown in table 3～table 6 in the lump.
[table 3]
[table 4]
[table 5]
[table 6]
Embodiment 1,30～32
Likewise make shown in the table 7 O/W emulsion composition of forming with embodiment 1～10, when carrying out the mensuration of viscosity and remnant of moisture content, the observation that epithelium is carried out the affirmation of lamellar structure through SAXS and carries out apparent condition through SEM.In addition, estimate the sense of touch and the outward appearance of the skin after moistening persistence, the coating.The result is shown in the table 7 in the lump.
[table 7]
Embodiment 1,30 makes through the 1A of manufacturing process, and embodiment 31 makes through the 1C of manufacturing process, and embodiment 32 makes through the 1D of manufacturing process.The embodiment 1 and the embodiment 30 that make through the 1A of manufacturing process that in oil phase, cooperates unneutralized composition (D); The evaluation of the slickness of the skin sense of touch after the coating is high; Confirm to suppress the lamellar structure that the ceramide crystallization is separated out, obtain the high result of moistening effect, and obtain high viscosity.
Claims (21)
1. the manufacturing approach of an emulsification composition, wherein,
Said manufacturing approach has: following composition (A), (B), (C), (D) and the water I that contains (F1) are mixed, then emulsifying and refrigerative operation 1; Then, composition (E) below further mixing and the operation 2 that contains the water II of (F2),
(A) chemical compound 0.001～10 quality % that representes by following general formula (1),
In the formula, Z
1Be illustrated in the structure that has the hydroxyl more than 2 on glycerol, anhydrosorbitol, Sorbitol or the sucrose residue, Y
1Expression ester bond or ehter bond, R representes that carbon number is 14～22 alkyl, n representes 1～4 number;
(B) being selected from carbon number is 14～22 higher alcohol and 0.001～10 quality % of the chemical compound more than a kind in the sterols;
(C) chemical compound 0.001～15 quality % that representes by general formula (2),
In the formula, R
1Expression is 4～30 straight chain, side chain or cyclic saturated or unsaturated alkyl by hydroxyl, carbonyl or amino replacement or not substituted carbon number; Z representes methylene, methine or oxygen atom; X
1, X
2And X
3Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently; X
4Represent hydrogen atom, acetyl group or glyceryl, or form oxo group with adjacent oxygen atom, still, X when Z is methine
1And X
2Any one for hydrogen atom another does not exist, work as X
4X when forming oxo group
3Do not exist; R
2And R
3Represent hydrogen atom, hydroxyl, methylol or acetyl-o-methyl respectively independently; R
4Expression replaced by hydroxyl, carbonyl or amino or not substituted main chain on had or do not had ehter bond, ester bond or an amido link carbon number be 5～60 straight chain, side chain or cyclic saturated or undersaturated alkyl; R
5The expression hydrogen atom, or expression has or does not have the saturated or undersaturated alkyl that the substituent total carbon atom number that is selected from hydroxyl, hydroxy alkoxy base, alkoxyl and the acetoxyl group is 1～30 straight or branched; Dotted portion representes it can is unsaturated bond;
(D) anion surfactant 0.00025～10 quality %;
(F1) water;
(E) be selected from water soluble polymer 0.001～6 quality % in alkyl-modified polyacrylic polyvinyl and the alkyl-modified polysaccharide polymer;
(F2) water.
2. the manufacturing approach of emulsification composition as claimed in claim 1, wherein,
Operation 1 is following operation 1A or operation 1B,
Operation 1A has: the operation of blending constituent that obtains containing the oil phase of composition (A), (B), (C) and unneutralized composition (D); With in this oil phase, mix the water I that contains (F1) and alkali, then emulsifying and refrigerative operation,
Operation 1B has: the operation of blending constituent of oil phase that obtains containing the salt of composition (A), (B), (C) and composition (D); With in this oil phase, mix the water I that contains (F1), then emulsifying and refrigerative operation.
3. the manufacturing approach of emulsification composition as claimed in claim 1, wherein,
Operation 1 is following operation 1C or operation 1D,
Operation 1C has: the operation that obtains containing the blending constituent of composition (A), (B) and oil phase (C); With in this oil phase, mix the water I contain unneutralized composition (D), (F1) and alkali, then emulsifying and refrigerative operation,
Operation 1D has: the operation that obtains containing the blending constituent of composition (A), (B) and oil phase (C); Contain the salt of composition (D) and water I (F1) with in this oil phase, mixing, then emulsifying and refrigerative operation.
4. like the manufacturing approach of each described emulsification composition in the claim 1～3, wherein,
Composition (A), (B), (C), (D) and mass ratio (E) do, (E)/and ((A)+(B)+(C))=0.0025～50, and (E)/(D)=0.025～100.
5. like the manufacturing approach of each described emulsification composition in the claim 1～4, wherein,
Composition (A) is for being selected from the chemical compound more than a kind in fatty acid monoglyceride, anhydrosorbitol mono fatty acid ester, anhydrosorbitol di fatty acid ester, Sorbitol mono fatty acid ester, Sorbitol di fatty acid ester, sucrose monofatty acid ester and the glycerol monoalkyl ether.
6. like the manufacturing approach of each described emulsification composition in the claim 1～5, wherein,
Composition (D) is the chemical compound in 12～24 soap, alkyl sulfate salt, alkyl ether sulfate, fatty acid amide sulfonate, alkylphosphonic, polyoxyethylene alkyl ether phosphate and the long-chain N-acyl glutamate for being selected from carbon number.
7. like the manufacturing approach of each described emulsification composition in the claim 1～6, wherein,
Said emulsification composition forms α-gel structure.
8. like the manufacturing approach of each described emulsification composition in the claim 1～7, wherein,
The viscosity of said emulsification composition under 25 ℃ is 10～8000dPas.
9. like the manufacturing approach of each described emulsification composition in the claim 1～8, wherein,
Said emulsification composition contains the composition (A) of 0.05～7 quality %, the composition (B) of 0.05～7 quality %, the composition (C) of 0.05～7 quality %, the composition (D) of 0.05～2 quality %, the composition (E) of 0.05～5 quality %.
10. like the manufacturing approach of each described emulsification composition in the claim 1～9, wherein,
Composition (A), (B), (C) and mass ratio (E) do, (E)/and ((A)+(B)+(C))=0.01～3.
11. like the manufacturing approach of each described emulsification composition in the claim 2～10, wherein,
Contained alkali is a kind or 2 kinds that is selected from arginine and the sodium hydroxide among the water I.
12. an emulsification composition, wherein,
Said emulsification composition contains following composition (A), (B), (C), (D), (E) and (F),
(A) single Compritol 888 ATO or single cetyl glycerin ether 0.001～10 quality %;
(B) hexadecanol or stearyl alcohol 0.001～10 quality %;
(C) ceramide type 0.001～15 quality % that representes by general formula (2),
In the formula, R
1Expression is 4～30 straight chain, side chain or cyclic saturated or unsaturated alkyl by hydroxyl, carbonyl or amino replacement or not substituted carbon number; Z representes methylene, methine or oxygen atom; X
1, X
2And X
3Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently; X
4Represent hydrogen atom, acetyl group or glyceryl, or form oxo group with adjacent oxygen atom, still, X when Z is methine
1And X
2Any one for hydrogen atom another does not exist, work as X
4X when forming oxo group
3Do not exist; R
2And R
3Represent hydrogen atom, hydroxyl, methylol or acetyl-o-methyl respectively independently; R
4Expression replaced by hydroxyl, carbonyl or amino or not substituted main chain on had or do not had ehter bond, ester bond or an amido link carbon number be 5～60 straight chain, side chain or cyclic saturated or undersaturated alkyl; R
5The expression hydrogen atom, or expression has or does not have the saturated or undersaturated alkyl that the substituent total carbon atom number that is selected from hydroxyl, hydroxy alkoxy base, alkoxyl and the acetoxyl group is 1～30 straight or branched; Dotted portion representes it can is unsaturated bond;
(D) stearyl glutamate, Glu, stearyl methyl tauride or polyoxyethylene stearyl base ether phosphate 0.00025～10 quality %;
(E) (acrylic acid/alkyl acrylate (C10-30)) copolymer, (alkyl acrylate/methacrylic acid stearyl alcohol polyethers-20) copolymer, laureth-13PG hydroxyethyl-cellulose or stearic oxygen base PG hydroxyethyl-cellulose sodium sulfonate 0.001～6 quality %;
(F) water.
13. emulsification composition as claimed in claim 12, wherein,
Composition (A) is single Compritol 888 ATO;
Composition (B) is a hexadecanol;
Composition (C) is the ceramide type by general formula (3) or general formula (4) expression,
In the formula, R
11Expression is 7～19 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl replacement or not substituted carbon number; Z
1Expression methylene or methine; X
5, X
6And X
7Represent hydrogen atom, hydroxyl or acetoxyl group respectively independently; X
8Represent hydrogen atom, or form oxo group, still, work as Z with adjacent oxygen atom
1X during for methine
5And X
6Any one for hydrogen atom another does not exist, work as X
8X when forming oxo group
7Do not exist; R
12Expression methylol or acetyl-o-methyl; R
13The expression hydrogen atom, or the expression carbon number is 1～4 alkyl; R
14Expression is replaced by hydroxyl or not substituted carbon number is 5～30 straight chain, side chain or cyclic saturated or undersaturated alkyl, or is illustrated on the ω end of this alkyl with ester bond and combines to be replaced or not substituted carbon number is the group that the saturated or undersaturated fatty acid of 8～22 straight or branched forms by hydroxyl; Dotted portion representes it can is unsaturated bond,
In the formula, R
15Expression is 10～22 straight chain, side chain or cyclic saturated or undersaturated alkyl by hydroxyl replacement or not substituted carbon number; X
9Expression hydrogen atom, acetyl group or glyceryl; R
16Expression is replaced by hydroxyl or amino or not substituted carbon number is 5～22 straight chain, side chain or cyclic saturated or undersaturated alkyl, or is illustrated on the ω end of this alkyl with ester bond and combines to be replaced or not substituted carbon number is the group that the saturated or undersaturated fatty acid of 8～22 straight or branched forms by hydroxyl; R
17The expression hydrogen atom, or expression is 1～30 alkyl by hydroxyl, hydroxy alkoxy base, alkoxyl or acetoxyl group replacement or not substituted total carbon atom number;
Composition (D) is the stearyl glutamate, Glu;
Composition (E) is (acrylic acid/alkyl acrylate (C10-30)) copolymer, (alkyl acrylate/methacrylic acid stearyl alcohol polyethers-20) copolymer, laureth-13PG hydroxyethyl-cellulose or stearic oxygen base PG hydroxyethyl-cellulose sodium sulfonate;
Composition (F) is a water.
14. like claim 12 or 13 described emulsification compositions, wherein,
Composition (A), (B), (C), (D) and mass ratio (E) do, (E)/and ((A)+(B)+(C))=0.0025～50 and (E)/(D)=0.025～100.
15. like each described emulsification composition in the claim 12～14, wherein,
Said emulsification composition forms α-gel structure.
16. like each described emulsification composition in the claim 12～15, wherein,
The viscosity of said emulsification composition under 25 ℃ is 10～8000dPas.
17. like each described emulsification composition in the claim 12～16, wherein,
Said emulsification composition contains the composition (A) of 0.05～7 quality %, the composition (B) of 0.05～7 quality %, the composition (C) of 0.05～7 quality %, the composition (D) of 0.05～2 quality %, the composition (E) of 0.05～5 quality %.
18. like each described emulsification composition in the claim 12～17, wherein,
Composition (A), (B), (C) and mass ratio (E) do, (E)/and ((A)+(B)+(C))=0.01～3.
19. each described emulsification composition is in the purposes that is used for making the skin smears in the claim 12～18.
20. each described emulsification composition is in the purposes that is used for making the moisture of skin retention agent in the claim 12～18.
21. each described emulsification composition is being used for making the purposes that the coated film of skin is formed agent in the claim 12～18.
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| US9339448B2 (en) | 2011-08-09 | 2016-05-17 | Kao Corporation | Emulsion composition |
| JP6076716B2 (en) * | 2012-12-03 | 2017-02-08 | 花王株式会社 | Emulsified cosmetics |
| JP6232285B2 (en) * | 2013-12-27 | 2017-11-15 | 花王株式会社 | Cosmetics |
| JP6624814B2 (en) * | 2015-05-29 | 2019-12-25 | 花王株式会社 | Skin cosmetics |
| JP2019196311A (en) * | 2018-04-16 | 2019-11-14 | ロレアル | Composition in form of o/w type |
| JP6469286B1 (en) * | 2018-06-20 | 2019-02-13 | 高級アルコール工業株式会社 | Novel composite and emulsion composition |
| JP2020200283A (en) * | 2019-06-11 | 2020-12-17 | 花王株式会社 | Sheet-like cosmetics |
| JP7395267B2 (en) * | 2019-06-19 | 2023-12-11 | 株式会社 資生堂 | oil-in-water cream cosmetics |
| JP7478534B2 (en) * | 2019-11-22 | 2024-05-07 | 花王株式会社 | Emulsion composition |
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Application publication date: 20121017 |