WO2002078650A1 - Preparation d'emulsion cosmetique et agent pour usage externe - Google Patents
Preparation d'emulsion cosmetique et agent pour usage externe Download PDFInfo
- Publication number
- WO2002078650A1 WO2002078650A1 PCT/JP2002/003203 JP0203203W WO02078650A1 WO 2002078650 A1 WO2002078650 A1 WO 2002078650A1 JP 0203203 W JP0203203 W JP 0203203W WO 02078650 A1 WO02078650 A1 WO 02078650A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyglycerin
- fatty acid
- weight
- acid ester
- polymerization
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 74
- 239000003795 chemical substances by application Substances 0.000 title claims 3
- 239000008271 cosmetic emulsion Substances 0.000 title 1
- -1 fatty acid ester Chemical class 0.000 claims abstract description 149
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 136
- 239000000194 fatty acid Substances 0.000 claims abstract description 136
- 229930195729 fatty acid Natural products 0.000 claims abstract description 136
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 72
- 239000000839 emulsion Substances 0.000 claims abstract description 62
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 61
- 150000004665 fatty acids Chemical group 0.000 claims abstract description 43
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 37
- 239000000787 lecithin Substances 0.000 claims abstract description 36
- 229940067606 lecithin Drugs 0.000 claims abstract description 36
- 235000010445 lecithin Nutrition 0.000 claims abstract description 36
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- 239000002537 cosmetic Substances 0.000 claims description 89
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
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- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 claims description 5
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- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 3
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 24
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- 235000021314 Palmitic acid Nutrition 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
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- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 6
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- 238000010998 test method Methods 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
Definitions
- the present invention relates to an emulsified cosmetic and an external preparation using a polydaliserine fatty acid ester as an emulsifying base in the fields of cosmetics, quasi-drugs, pharmaceuticals, household goods, and the like. , No significant decrease in hardness at temperatures higher than 40 ° C, no increase in hardness over time even at 0 ° C, good texture, and no white residue when applied on skin
- the present invention relates to emulsified cosmetics and external preparations that are panicked.
- the average particle size is 100 nm or less, the appearance is transparent, and it is transparent over time.
- a transparent emulsified cosmetic that is stable without turbidity due to reduced properties and stable without separating components, and has almost no decrease in pH, which is often seen in aqueous compositions using a combination of polyglycerin fatty acid ester and lecithin. And external preparations. Background art
- emulsified cosmetics and solubilizing cosmetics or oils containing finely dispersed oily ingredients such as ointments, creams, emulsions, serums, lotions, lotions, and colognes are used as emulsifiers or solubilizers.
- Polyoxyethylene-based surfactants are used. Polyoxyethylene surfactants are widely used because they can be used as emulsifiers or solubilizers, and because of their structural characteristics, especially because they can freely control the chain length of hydrophilic groups in molecules, Products with high HLB values are on the market.
- HLB can be adjusted by using a single surfactant or a combination of surfactants, a fine emulsion can be easily formed, and it can be easily introduced into a phase inversion emulsification method.
- an emulsion is usually produced by dissolving or dispersing a surfactant in an oil phase, adding an aqueous phase, and inverting the phase from W / O type to O / W type.
- the dispersion emulsification method in which the oil phase is added to the aqueous phase, Since a good emulsion having a small particle size can be obtained, it is used as a usual method for producing cosmetics and external preparations. It is also reported that the balance between hydrophilicity and lipophilicity is related to the lamellar liquid crystal generated during phase inversion (Yuyo Kagaku Vol. 30 No. 1-1989).
- micelles may be dissolved and solubilized by a surfactant having a high HLB value.
- Advantages of such cosmetics and external preparations are that they provide a refreshing feel without oiliness even if oily components are contained, and that they can stably blend oily components without increasing the viscosity of the system. Presents an aesthetic appearance. These merits provide high commercial value. ⁇
- polyglycerol fatty acid esters which are highly safe surfactants, are sometimes used.
- Polyglycerol a component of polyglycerol fatty acid esters that are generally widely distributed, has an average degree of polymerization of 2 to 10 determined from the hydroxyl value, and the HLB can be adjusted to some extent by the composition and amount of the esterified fatty acid. You.
- Such polyglycerin is generally obtained by a dehydration condensation reaction, is inexpensive in cost, and is widely used for food applications.
- polyglycerin fatty acid esters have limitations in view of their use as hydrophilic surfactants for cosmetics.
- the average degree of polymerization of the polyglycerin obtained by the above-mentioned dehydration condensation reaction is 2 to 10, but the reason why higher average degree of polymerization is not distributed is that if the degree of polymerization is high, it is insoluble during the reaction. It becomes a rubbery state and loses the inherent hydrophilic properties of polyglycerin. This is because when the degree of polymerization is increased to a certain level or more, cyclic and steric bonds increase. As a characteristic of polyglycerin obtained by the dehydration condensation reaction, the distribution of polymerization degree of the components is wide.
- This fatty acid ester of polyglycerin has a lower hydrophilicity than expected from the average degree of polymerization of polyglycerin.
- the HLB value obtained from an emulsification experiment is 1 It is not so high, about 1 ⁇ 12.
- the HLB value naturally becomes higher (for example, in the case of lauric acid, the HLB value is about 15), but the emulsifying ability of the higher fatty acid is higher than that of the middle fatty acid.
- oils to be emulsified having various polarities and molecular weights.
- hydrocarbon oils and ester oils do not have uniform polarities and molecular weights.
- the HLB value required for highly polar oils, such as ester oils and alcohols is not uniform. In order to produce a fine emulsion, it is necessary to mix surfactants with high and low HLB values to adjust the HLB value appropriately.
- Fatty acid esters of polyglycerin which have a wide average polymerization degree distribution and a high average polymerization degree obtained from the dehydration condensation reaction that has been distributed in the past, have an HLB value that is not so high. Therefore, when such an ester is used, it is difficult to obtain a good emulsion.
- straight-chain saturated higher alcohol / alkyl glyceryl ether is commonly used.
- the phase inversion emulsification method is effective for adjusting the hardness, and a liquid crystal is formed on the oil-water interface by using an emulsifying aid such as a higher alcohol together with a surfactant.
- Emulsification methods such as the D-phase emulsification method and the liquid crystal emulsification method, have been developed as methods for easily producing emulsions. These emulsification methods are convenient because there is almost no need for HLB adjustment, but the higher alcohols are difficult to orientate effectively at the oil-water interface, making it difficult to adjust the hardness and often failing to achieve the desired hardness. Increasing the amount of higher alcohol increases the hardness, but reduces the texture of the appearance, leaving white spots on the skin when applied, causing the so-called no burnishing, resulting in low commercial value. There is a problem of becoming a product. Vanish here means that it penetrates immediately without leaving white on the skin.
- polyglycerol fatty acid esters with high hydrophilicity there are several methods for obtaining polyglycerol fatty acid esters with high hydrophilicity.
- the former high hydrophilicity is caused by the difficulty in cyclization due to the reaction characteristics.
- Polyglycerol having a low polymerization component and a narrow polymerization degree distribution can be obtained by a synthesis method in which the reaction process is controlled (Japanese Patent Application Laid-Open No. 7-1000355). Further, an example of a fatty acid ester of polyglycerin having high purity is disclosed in Japanese Patent Application Laid-Open No. 62-266135. In addition, a technology for removing low-polymerization parts from polyglycerin by column fractionation has been developed and already industrialized, and fatty acid esters thereof have been developed (Japanese Patent Application Laid-Open No. Hei 8-14413513). ).
- Lecithin not only acts as a surfactant, but also interacts with water to form lamellar liquid crystals, so that water is easily retained and is useful as a component of moisturizing cosmetics.
- polyglycerin fatty acid ester and lecithin are used in combination in cosmetics and external preparations, the emulsifying performance can be enhanced as compared with the case where each is used alone.
- polyglycerin fatty acid ester may be used as a dispersant for lecithin in water.
- the effect of polyglycerin polymerization degree distribution on the emulsification performance of polyglycerol fatty acid esters has been reported in terms of phase behavior (The 37th Oil Chemistry Symposium Proceedings, p. 109 , 1989).
- the density of the surfactant at the oil-water interface is related to the degree of polymerization of polyglycerin, and it is suggested that the wider the degree of polymerization, the higher the interface density and the higher the emulsifying performance. I have.
- a polyglycerin fatty acid ester having a narrow polymerization degree distribution or a single polyglycerin fatty acid ester is used as an emulsifying base, there is an advantage that a polyglycerin fatty acid ester having high hydrophilicity can be obtained.
- a composition containing a higher alcohol or an alkyl glyceryl ether for adjusting the hardness of a cosmetic or an external preparation has a poor texture in appearance, lacks luster, has no luster, and is white when applied to the skin. There is a problem that the emulsion easily remains and hardly burnishes.
- Japanese Patent Application Laid-Open No. 58-185 5 3 The polyglycerol ester of a branched fatty acid disclosed in Japanese Patent Publication No. 7 has a lower melting point than the polyglycerol fatty acid ester of a saturated linear higher fatty acid, and has less change in viscosity due to temperature change, but the obtained product is soft. . If the amount of high-grade alcohol is increased to increase the hardness, the above-mentioned problems occur.
- the conventional guaranteed temperature for distribution of cosmetics and external preparation products was 40 ° C.
- the temperature condition of the preservation test used for cosmetics and external preparations is 40 ° C, and this temperature is also used for the accelerated test.
- the average temperature has risen more than ever due to global warming due to the ozone layer destruction and urban warming, especially in the urban area and its suburbs during summertime.
- the temperature is often increasing to 35 ° C or more.
- the temperature in air-conditioned indoors and carrying bags often exceeds 40 ° C.
- the hardness of cosmetics and external preparations is extremely reduced, causing them to spill vigorously upon removal from the container, causing leakage from the container, and furthermore, the oil layer is separated over time. Frequency increases.
- a first object of the present invention is an emulsified composition using a polyglycerin fatty acid ester as an emulsifying base, wherein a polyglycerin fatty acid ester having a high HLB is used so as to be easily used in the phase inversion emulsification method. No significant decrease in hardness at temperatures higher than 40 ° C, and is stable over time when stored, and stable even at 0 ° C without increasing the hardness over time. And the appearance is fine
- the object of the present invention is to provide an emulsified cosmetic and an external preparation, which have a good finish and do not leave white on the skin when used, and smoothly burnish.
- a second object of the present invention is a transparent and fine emulsified cosmetic using a polyglycerin fatty acid ester and lecithin as an emulsifying base, and which has good transparency without deterioration or separation over time.
- An object of the present invention is to provide a transparent emulsified cosmetic and an external preparation having emulsification stability and particularly good pH stability.
- the transparent cosmetics referred to here are defined as having a transmittance of 50% T or more, preferably with purified water at a measurement wavelength of 75 nm and a measurement optical path of 1 Omm using a spectrophotometer. 70% ⁇ or more. Disclosure of the invention
- the present inventors have conducted intensive studies to solve the above-mentioned problems, and found that HLB and specific weight
- the above-mentioned problems can be solved by a hydrophilic and lipophilic polyglycerol fatty acid ester having a specified content, a fatty acid residue, etc., and an emulsified cosmetic or external preparation containing a specific emulsifying aid as an essential component.
- the inventors have found that the present invention can be solved, and have completed the present invention.
- the first embodiment of the present invention provides (A) a hydrophilic surfactant having an HLB value of 13 or more and an average degree of polymerization of polyglycerin of 8 to 12, pentamer and hexamer. Is 50% by weight or more, the total content of tetramers or less is less than 20% by weight, and the fatty acid residue is a linear alkyl group having 14 to 22 carbon atoms. Polyglycerol fatty acid ester, (B) As a lipophilic surfactant, HLB value is 5 to 11, polyglycerin has an average degree of polymerization of 2 to 12, and a total content of not more than tetramer of 20 weight.
- the fatty acid residue is a polyglycerol fatty acid ester having a linear alkyl group having 14 to 22 carbon atoms; It is intended to provide an emulsified cosmetic and an external preparation containing, as essential components, a saturated linear alcohol having 6 to 22 or a linear monoalkyl glyceryl ether having 16 to 22 carbon atoms.
- the second aspect of the present invention provides (D) a hydrophilic surfactant having an HLB value of 13 or more, polyglycerin having an average degree of polymerization of 8 to 12 and a pentamer And the total content of hexamers is 50% by weight or more, the total content of tetramers or less is less than 20% by weight, and the fatty acid residue is a hydrocarbon having 14 to 22 carbon atoms.
- a hydrophilic surfactant having an HLB value of 13 or more, polyglycerin having an average degree of polymerization of 8 to 12 and a pentamer And the total content of hexamers is 50% by weight or more, the total content of tetramers or less is less than 20% by weight, and the fatty acid residue is a hydrocarbon having 14 to 22 carbon atoms.
- the HLB value is 5 to 11
- the polyglycerin has an average degree of polymerization of 2 to 12 and a tetramer or less.
- n is 2 or more
- n is 2 or more
- n ((2/3) If ⁇ does not become a natural number, 2) 3) at least 5% by weight of each component (the smallest natural number exceeding ⁇ ), and the fatty acid residue is a hydrocarbon group having 14 to 22 carbon atoms.
- a transparent emulsified cosmetic and an external preparation comprising an essential polyglycerol fatty acid ester, (F) lecithin, and (G) an oily component, and having an average particle diameter of 100 nm or less. Things.
- the average degree of polymerization refers to the average degree of polymerization obtained from the hydroxyl value, which is used for generally distributed polyglycerin.
- the composition of polyglycerin is the result of component analysis by analytical methods such as gas chromatography and liquid chromatography.
- polyglycerin refers to a mixture of glycerin polymers having different degrees of polymerization and a case where unreacted free glycerin remains.
- the average degree of polymerization of polyglycerin in the present invention is determined from the hydroxyl value of a standard fat and oil analysis test method (edited by the Japan Oil Chemists' Society).
- a polyglycerin derivative for the measurement of the component composition of each degree of polymerization, it is appropriate to use a polyglycerin derivative, and then perform the separation and quantification by GC (gas chromatography).
- Analysis by GC method for example, using a fused silica capillary tube chemically bonded to a low-polarity liquid phase such as methyl silicon, raises the temperature from 100 ° C to 250 ° C by 10 ° C / min. The analysis can be easily implemented.
- the degree of polymerization of the peak on the gas chromatogram can be identified by, for example, introducing a gas chromatograph into a double-focusing mass spectrograph, ionizing it by a method such as chemical ionization, and then measuring the parent ion. This can be easily performed by determining the molecular weight of the peak on the gas chromatogram from the molecular weight, and further determining the degree of polymerization of glycerin from the chemical formula. However, it is not limited to this method.
- the average degree of polymerization of polyglycerin from the hydroxyl value it is assumed that the polyglycerin having the average degree of polymerization n has (n + 2) hydroxyl groups. Since the presence of cyclized polyglycerin and the presence of hydroxyl groups that are difficult to react during analysis are not taken into account, a higher average polymerization degree is often obtained than the result of component analysis by gas chromatography-liquid chromatography.
- an emulsion of liquid paraffin is prepared by combining a hydrophilic and lipophilic surfactant with a known HLB value, and the required HLB of liquid paraffin is calculated from the combination that produces the best oil-in-water emulsion.
- This method involves emulsifying paraffin and calculating the ratio of the best oil-in-water emulsion to be produced, and the HLB value of the polyglycerol fatty acid ester from the required HLB.
- HLB value 15.0
- HLB value 15.0
- the HLB value of the polyglycerol fatty acid ester of the present invention can be directly obtained by the Griffin's empirical formula, but there may be a difference compared to the method obtained by an emulsification experiment (Sakamoto Pharmaceutical Co., Ltd.) Polyglycerin ester, see page 107).
- FIG. 1 is a graph showing the viscosity of talmes against temperature.
- the emulsifier of the present invention requires a combination of a polyglycerin fatty acid ester having an HLB value of 13 or more and a polyglycerin fatty acid ester having an HLB value of 5 to 11 and is used after adjusting the HLB according to the oil to be emulsified. . Even when a single polyglycerol fatty acid ester is used, or when polyglycerol fatty acid esters with HLB values outside the above range are combined, an emulsion is formed if the entire system has a specific range of HLB, A good emulsion having emulsion stability and hardness stability at temperature cannot be obtained. In addition, a good emulsion having good particle size, transparency, and emulsion stability over time cannot be obtained.
- the details of each polyglycerin fatty acid ester used in the present invention will be described.
- the polyglycerol fatty acid ester having high hydrophilicity used in the present invention needs to have an HLB value of 13 or more, and preferably 13 to 17. If it is lower than 13, the phase inversion emulsification is difficult, so that the HLB value is difficult to adjust, and it is difficult to produce a good emulsion. Emulsions with good kino are not formed, and emulsion stability and hardness stability cannot be obtained at temperatures higher than 40 ° C.
- the average degree of polymerization needs to be from 8 to 12, and preferably from 10 to 12.
- the HLB value is difficult to adjust due to low hydrophilicity.
- Polyglycerin larger than 1 2 does not produce a good emulsion, causing problems such as poor texture, poor hardness, large average particle size, and poor high-temperature stability. Not suitable for the present invention.
- the total content of pentamer and hexamer must be 50% by weight or more, and is 70% by weight. / 0 or more is preferable. 50 weight. If the ratio is less than / 0 , the emulsion stability at high temperature and the maintenance of the hardness become poor, and problems such as a decrease in pH occur.
- the content of the tetramer or less is 20 weight. Must be less than / 0 and 10 weight. / 0 or less is preferable.
- a glycerin polymer of a heptamer or more may be contained in an amount of 0 to 30% by weight as a secondary component. It is general and there is no problem that it is included to some extent in the present invention. However, when a glycerin polymer of 7 or more is contained as a main component, a good emulsion is not formed, and good texture, hardness, high-temperature stability, and emulsion stability cannot be obtained. This is not suitable for the present invention because problems such as a decrease in H occur.
- the fatty acid residue constituting the polyglycerin fatty acid ester must be a straight-chain alkyl group having 14 to 22 carbon atoms, and may be a straight-chain alkyl group having 16 to 18 carbon atoms. preferable. Produces a good emulsion with emulsification stability and solidity stability over a wide range of temperatures by being a linear alkyl group having 14 to 22 carbon atoms can do. Generally, myristic acid, palmitic acid, stearic acid, behic acid and the like can be exemplified.
- Lauric acid and hydropuric acid having less than 14 carbon atoms do not meet the purpose of the present invention because they have no emulsion stability at a temperature higher than 40 ° C. and have a reduced hardness.
- Unsaturated fatty acids and branched fatty acids are not suitable for the first object of the present invention because the composition does not have hardness and are not stable at temperatures higher than 40 ° C. ,. As long as the first object of the present invention is not affected, there is no problem in containing trace amounts of other fatty acids for the purpose of fine adjustment of the function.
- the lipophilic polyglycerol fatty acid ester used in the first embodiment of the present invention needs to have an HLB value of 5 to 11, preferably 8 to 11. If the strength is out of the range, it is difficult to perform phase inversion emulsification, and it is difficult to produce a good emulsion. Emulsions with good texture are not produced, and emulsion stability and hardness stability cannot be obtained at temperatures higher than 40 ° C.
- the average degree of polymerization of the polyglycerol constituting the polyglycerin fatty acid ester is 2 to 12, preferably 4 to 12, and more preferably 6 to 12.
- the total content of tetramers or less is 20% by weight or more.
- the number of (2Z3) n components (or the lowest natural number exceeding (2/3) n if (2Z3) n is not a natural number) At least 5% by weight of each, and preferably (1/3) n ((1 3) If n is not a natural number, the minimum exceeding (1/3) n Polyglycerin containing 10% by weight or more of each component (natural number) or more ((1 2) n (If (1/2) n is not a natural number, (1 2) the lowest natural number exceeding n) or more) Each 8 weight. /.
- the polyglycerin contains at least 3% by weight of each of the (n-1) components.
- the component having the highest degree of polymerization is 50% by weight or less, particularly 30% by weight or less.
- those obtained by the dehydration condensation reaction, dalicidole dipiclorhydrin, A method using hydrin, dichlorohydrin or the like as a starting material is suitable, but not limited thereto.
- low-polymerized substances may be intentionally reduced by reaction conditions or multi-step reactions to produce polyglycerin having a narrow distribution of polymerization degree, but such polyglycerin is not suitable.
- the fatty acid residue constituting the polyglycerin fatty acid ester must be a linear alkyl group having 14 to 22 carbon atoms, and is a linear alkyl group having 16 to 18 carbon atoms. Preferably, there is.
- myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid can be exemplified.
- the number of carbon atoms is smaller than 14, for example, lauric acid / capric acid does not meet the first object of the present invention because of lack of emulsification stability at a temperature higher than 40 ° C. and reduced hardness. .
- Unsaturated fatty acids and branched fatty acids for example, disostearic acid oleate, do not have rigidity and are not stable at temperatures higher than 40 ° C., and thus do not meet the first object of the present invention. As long as the first object of the present invention is not affected, a small amount of these fatty acids may be included.
- the ratio of the polyglycerol fatty acid ester having an 118 value of 13 or more to the polyglycerin fatty acid ester having an HLB value of 5 to 11 is preferably 20: 1 to 1: 4, and particularly preferably 10: 1 to 1: 2.
- the (A) hydrophilic surfactant in the emulsified cosmetic composition and the external preparation of the first embodiment of the present invention has an HLB value of 13 or more, and has an average polyglycerol polymerization degree of 8 to 12 or pentamer.
- the total content of the hexamer is 50% by weight or more, the total content of the tetramer or less is less than 20% by weight, and the fatty acid residue is a straight chain having 14 to 22 carbon atoms.
- Polyglycerol fatty acid ester which is a chain alkyl group and (B) lipophilic surfactant having an HLB value of 5 to 11 and an average degree of polymerization of polyglycerin of 2 to 12 and a total of tetramers or less If the content is 20% by weight or more and the average degree of polymerization is n (n is 2 or more), (2/3) n ((2 3) If n is not a natural number, (2 3 ) At least five components each of the smallest natural number that exceeds n) amount.
- the total amount of the polyglycerol fatty acid ester in which the fatty acid residue is a linear alkyl group having 14 to 22 carbon atoms is preferably 0.1 to 10% by weight. 0.2 to 8% by weight is particularly preferred.
- saturated linear alcohol having 16 to 22 carbon atoms used in the first embodiment of the present invention include cetanol, stearyl alcohol, cetstearyl alcohol, and behenyl alcohol.
- straight-chain monoalkyl glyceryl ether having 16 to 22 carbon atoms include monocetyl dalyseryl ether (chimylanolole), monostearyl glyceryl / lethethenole (batyl alcohol), and monobenhenyl glyceryl ether. These can be used alone or as a mixture.
- the emulsified cosmetic and the external preparation of the first embodiment of the present invention may contain an oily component, and there is no problem as long as it is an oily component generally used in cosmetics and external preparations.
- oils include natural animal and vegetable fats and oils, semi-synthetic fats and oils, hydrocarbon oils, higher fatty acids, ester oils, silicone oils, essential animal and vegetable and synthetic essential oil components, fat-soluble vitamins, and the like.
- Natural animal and vegetable oils and fats and semi-synthetic oils include apogado oil, linseed oil, harmony oil, olive oil, carnauba wax, candelillaro, tallow, beef tallow, beef bone, hardened tallow, wheat germ oil, sesame oil, Rice germ oil, rice bran oil, safflower oil, soybean oil, camellia oil, evening primrose oil, corn oil, rapeseed oil, horse fat, palm oil, palm kernel oil, castor oil, hardened castor oil, castor oil, hohopa oil, macadamia nut oil , Millo ⁇ , mink oil, cottonseed oil, coconut oil, hydrogenated coconut oil, peanut oil, lanolin, liquid lanolin, reduced lanolin, isopropyl lanolin fatty acid and the like.
- the hydrocarbon include squalane, squalene, ceresin, paraffin, barrafin wax, liquid paraffin, microcrystalline wax, petrolatum, and the
- higher fatty acids examples include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, pendecilenic acid, oleic acid, linoleic acid, linolenic acid, isostearic acid, and 12-hydroxyxtearic acid.
- ester oils diisobutyl adipate, 2-hexyldecyl adipate, di-2-adipate, heptyl pendecyl, isostearyl isostearate, trimethylolpropane triisostearate, cetyl 2-ethylhexyl, cetyl hexanoate, and di-ethylinohexane
- Neopentyl glycol acid trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl octanoate, oleinole oleate, octayldodecyl oleate, decinole oleate, neo dicaprate Pentyl glycol, 2-ethynolehexyl succinate, isosecetyl stearate, butyl stea
- glyceride oils include glyceryl triisostearate, glyceryl triisonoremitinate, glyceryl tri-2-ethylhexanoate, glyceryl trimyristate, glyceryl diparamethoxy cinnamate and glyceryl monoisooctylate.
- Silicone oils include higher alkoxy-modified silicones such as dimethylpolysiloxane, methylphenolpolysiloxane, methinolehydrogenpolysiloxane, otatamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and stearoxysilicone, and alkyl. Modified silicones, higher fatty acid ester-modified silicones, and the like. Examples of fat-soluble vitamins include tocofurol and its derivatives, retinol and its derivatives.
- oil component used in the first embodiment of the present invention is not limited to these.
- hydrocarbon oil as a main material (50% by weight or more).
- the oil component is not essential, but is usually used in an amount of 100 times or less the total amount of the polyglycerin fatty acid ester.
- the emulsification stability and the solidity stability at a temperature higher than 40 ° C which are the object of the present invention, are set particularly at around 45 ° C.
- Stability and firmness stability can be achieved by combining saturated lecithin.
- lecithin saturated lecithin
- lecithin saturated lecithin
- saturated lecithin examples include soybean lecithin and egg yolk lecithin, which can be obtained as ordinary commercial products and reagents, as well as purified lecithin and fractionated lecithin obtained by subjecting these to processing such as solvent separation, extraction, and fractionation, followed by processing. Among them, those obtained by adding hydrogen to increase the degree of saturation are particularly preferable. It mainly consists of saturated linear dialkyl phosphatidylcholine having 12 to 22 carbon atoms, dianolekiloinole phosphatidinolethananolamine, and dianolekiloinole phosphatidinoleinositol. Also, lysolecithin can be used since it has the same effect. '
- sterol esters are mentioned as substances that can achieve the same effect as lecithin.
- the components of sterol esters are divided into sterols and fatty acids.
- sterols include cholesterol and phytosterols, and esters thereof include oleic acid, palmitoleic acid, ricinoleic acid, stearic acid, palmitic acid, myristic acid, lauric acid, and 12-hydroxy. Esters with stearic acid and the like can be mentioned, but their origin does not matter.
- the emulsified cosmetic and the external preparation of the first embodiment of the present invention may contain known components used in those fields as long as the properties of the present invention are not impaired.
- Aqueous component such as edetate disodium
- Powder component such as talc, silica, kaolin, magnesium oxide
- Moisturizing component such as sorbitol, propylene glycol, lactic acid, polyethylene glycol, etc .
- Roxypoxymethyl polymer Ripoxymethyl cell mouth Thickeners such as glucose, polybutyl alcohol and carrageenan
- pH regulators such as sodium lactate-lactate and sodium citrate-taenoate
- antioxidants such as butylhydroxytoluene and sodium bisulfite
- methyl paraben benzoic acid
- Preservatives such as sodium acid
- ultraviolet protective agents such as para-aminobenzoic acid and octylcinnamate.
- the emulsified cosmetic and the external preparation of the first embodiment of the present invention include, for example, mixing, stirring and dissolving the components (A), (B), (C) and, if necessary, oily components, It can be manufactured by mixing other components according to the above and emulsifying the phase inversion.
- the temperature during the phase inversion emulsification is preferably from 40 to 90 ° C, particularly preferably from 50 to 80 ° C.
- the concept of the decrease in hardness is summarized as follows. If it is a liquid, the hardness generally decreases when the temperature is increased, but creams and emulsions using higher alcohols contain higher alcohols. It is known that a surfactant and a liquid crystal are formed, and a solid is obtained. The internal structure of the liquid crystal is variable depending on the temperature. If the temperature is high, the structure disappears, and the hardness rapidly decreases. However, according to the composition of the first embodiment of the present invention, it is not clear, but it is difficult to lower the hardness due to the reason that the interface density becomes high or the interface becomes rigid. As for the evaluation of hardness, if the hardness can be measured with a B-type viscometer, it is appropriate to evaluate the viscosity, and if it is harder than that, it is appropriate to measure penetration using a penetometer. is there.
- the fatty acid residue constituting the polyglycerin fatty acid ester in the second embodiment of the present invention is a hydrocarbon group having 14 to 22 carbon atoms, and the hydrocarbon group includes a straight-chain alkyl group and a branched-chain alkyl group. And alkenyl groups are preferred.
- myristic, norremitic, stearic, behe / acid, palmitoleic, oleic examples thereof include isopalmitic acid and isostearic acid. Since the number of carbon atoms is less than 14, for example, lauric acid or phosphinic acid has poor emulsification stability and becomes cloudy over time, it does not meet the second object of the present invention. As long as it does not affect the second object of the present invention, there is no problem in including other fatty acids for fine adjustment of the function.
- the lipophilic polyglycerin fatty acid ester used in the present invention needs to have an HLB value of 5 to 11, and preferably 8 to 11. If the ratio is out of this range, the emulsion stability is poor, and the emulsion becomes cloudy over time.
- the fatty acid residue constituting the polyglycerin fatty acid ester is a hydrocarbon group having 14 to 22 carbon atoms, and the hydrocarbon group is preferably a linear alkyl group, a branched alkyl group, or an alkenyl group. .
- the weight ratio of the polyglycerol fatty acid ester having an 118 value of 13 or more to the polyglycerin fatty acid ester having an HLB value of 5 to 10 is preferably 20 ::! To 1: 4, and 10: 1 to 1: 2. Is particularly preferred.
- the external surfactant, the HLB value is 13 or more
- polyglycerin has an average degree of polymerization of 8 to 12
- the total content of pentamer and hexamer is 50% by weight or more, the total content of tetramer or less is less than 2% by weight, and the fatty acid residue has 14 carbon atoms.
- the total content of tetramers or less is 20% by weight or more, and when the average degree of polymerization is n (n is 2 or more), (2/3) n ((2-3) n)
- the components of (the smallest natural number exceeding (2 Z 3) n) should be at least 5 weight each. / 0 or more, and polyglycerol fatty acid ester whose fatty acid residue is a hydrocarbon group having 14 to 22 carbon atoms.
- the amount is preferably from 0.1 to 10% by weight, preferably from 0.2 to 8% by weight. / 0 is particularly preferred.
- lecithin component (F)
- lecithin includes soybean lecithin and egg yolk lecithin, which can be obtained as ordinary commercial products and reagents, and is subjected to processing such as solvent separation, extraction, and fractionation.
- Lecithin and fractionated lecithin are used.
- those obtained by further hydrogenating them to increase the degree of saturation are appropriate.
- the phosphatidylcholine concentration in the phospholipid component is 50% by weight or more, especially the alkyl phosphatidylcholine concentration is 50% by weight or more, and the phosphatidylinositol concentration is 3% by weight.
- lecithin with an alkylol phosphatidyl inositol concentration below the detection limit is suitable.
- These are generally obtained by alcohol extraction or column fractionation, but are not limited thereto.
- those obtained by chemical synthesis those extracted from nature are suitable from the viewpoint of cost.
- lysolecithin obtained by enzymatic conversion or chemical synthesis falls within this range.
- the ratio of lecithin to polyglycerin fatty acid ester is preferably 1:20 to 4: 1, and particularly preferably 1:15 to 3: 1.
- the content of lecithin in the transparent emulsified cosmetic of the second embodiment of the present invention and the external preparation is preferably from 0.1 to 10% by weight, particularly preferably from 0.2 to 8% by weight.
- An oil component ((G) component) is used in the transparent emulsified cosmetic composition and the external preparation of the second embodiment of the present invention.
- an oily component used in cosmetics and external preparations, but a liquid or pasty oily component at room temperature is particularly suitable.
- Carnaubaro II candelilla wax, beef leg fat, beef bone fat, hardened tallow, hardened castor oil, beeswax, hardened coconut oil, hydrocarbon oil Except for ceresin, paraffin, paraffin wax, microcrystalline wax, and higher fatty acids, a hydrocarbon oil to which an olefin oligomer is added is a second type of oil component.
- the weight ratio of the sum of the polyglycerin fatty acid ester and lecithin to the oily component is preferably 100: 1 to 1: 2. If there is no oily component, the emulsion stability and the pH are lower. Qualitativeness is impaired.
- the amount of the oil component is preferably 0.01 to 10% by weight.
- the fatty acid residue is an oily component that is effective for emulsion stability.
- sterol esters preferably contained in the oily component.
- the components of the sterol ester are as described in the first embodiment.
- the stability of pH over time correlates with the emulsification stability. When the emulsification stability is good, the pH does not easily decrease, and when the emulsification stability is poor, the pH tends to decrease.
- the composition of the second embodiment of the present invention it is not clear, but because the interface density is high or the interface is rigid, the substrate of the hydrolysis reaction on the ester site is less likely to attack. It is assumed that
- the transparent emulsified cosmetic and external preparation of the second embodiment of the present invention require the emulsion to have an average particle diameter of 100 nm or less, and preferably 80 nm or less.
- the emulsion having such an average particle diameter can be obtained by adjusting the ratio of hydrophilic polyglycerin fatty acid ester, lipophilic polyglycerin fatty acid ester, and lecithin in accordance with the vicinity of the required HLB of the oil component.
- the average particle size is measured by laser scattering light spectroscopy.
- transparent cosmetics means that when the measurement wavelength is 750 nm and the measurement optical path is 10 mm using a spectrophotometer, the transmittance is 50 ° / oT or more, preferably 70%, using purified water as a control. %% or more.
- the transparent emulsified cosmetic and external preparation of the second embodiment of the present invention include, for example, mixing, stirring and dissolving the above components (D), ( ⁇ ), (F) and (G), It can be manufactured by mixing, stirring and emulsifying other components.
- the temperature at this time is from 40 to 90 ° (: particularly preferably from 50 to 80 ° C.
- the HLB of both polyglycerin fatty acid esters can be determined by appropriately selecting the stirring conditions and the like at this time. By appropriate adjustment, the average particle diameter can be reduced to 100 nm or less.
- the transparent emulsified cosmetic and the external preparation of the second embodiment of the present invention can be applied to products without a preservative as an additive component from the viewpoint of safety.
- the form of the emulsified cosmetic composition and the external preparation of the present invention is not particularly limited, and may be in any form such as cream, milky lotion, serum, ointment, jewel, lotion, pack and the like.
- the emulsified cosmetic composition and the external preparation of the present invention can be used in various forms by ordinary use.
- a 5-liter four-necked flask was charged with 330 g of diglycerin and 800 g of a 50% aqueous sodium hydroxide solution, and heated to 140 ° C. while removing water under a nitrogen stream. After distillation of water was completed, dichlorohydrin (640 g) was added dropwise over 2 hours. After the dropwise addition, the mixture was stirred at 120 ° C for 2 hours. After removing excess diglycerin by molecular distillation, it was diluted with water, decolorized and desalted with activated carbon and ion exchange resin, and water was removed to obtain polyglycerin. The hydroxyl value of this product was measured, and the average degree of polymerization was calculated to be 10.
- Polyglycerin lOOOg from Polyglycerin Production Example 1 was added to a simulated moving bed type chromatograph device composed of four columns packed with 10 ml of calcium ion exchange resin with 10% of crosslinking and 12% of cross-linking degree. Was drained. However, the ratio of supply, discharge time and circulation time was set to 2: 1. The effluent was measured with a refractometer, polyglycerin having a degree of polymerization of 3 or more was fractionated, and dehydrated and concentrated using a rotary evaporator to obtain polyglycerin. The same operation was further performed four times using the same column.
- the average degree of polymerization was 11, and the composition was 1% free glycerin, 1% dimer, 2% trimer, 6% tetramer, and 58 ° / pentamer.
- the hexamer component was 18%
- the octamer component was 4%
- the 9-mer component was 2%
- the 10-mer component was 2%
- the 11-mer was 3% or more.
- a 500 milliliter four-necked flask was charged with 259.7 g of the polyglycerin obtained in Production Example 1, 88.2 g of stearic acid, and 0.1 lg of tripotassium phosphate, and the generated water was removed under a nitrogen stream. While reacting at 250 ° C., 0.3 milliliter of phosphoric acid was added after the reaction to obtain polyglycerol stearate. The acid value of this ester was 1.0. The HLB value of the polyglycerin stearate was 13.4.
- Polyglycerol stearate was obtained in the same manner as in Synthesis Example 1 except that the polyglycerin obtained in Production Example 2 was used instead of the polyglycerin obtained in Production Example 1.
- the acid value of this ester was 1.0.
- the HLB value of polyglycerin stearate was 13.9.
- polyglycerin myristic acid ester was obtained in exactly the same steps as in Synthesis Example 1, and the acid value of this ester was 1.0.
- the HLB value was 15.0.
- Polyglycerol isostearate was obtained in exactly the same steps as in Synthesis Example 1 from 2 10 g of the polyglycerin obtained in Production Example 1 and 90 g of isostearic acid. The acid value of this ester was 1.2. The HLB value of polyglycerin isostearate was 13.0.
- Polyglycerol laurate was obtained by exactly the same process as in Synthesis Example 1, using 210 g of the polyglycerin obtained in Production Example 2 and 52.5 g of lauric acid. The acid value of this ester was 1.0. The HLB value of polyglycerin laurate was 15.6.
- Polyglycerol laurate was obtained in exactly the same manner as in Synthesis Example 1 using 210 g of the polyglycerin obtained in Production Example 2 and 52.5 g of lauric acid. The acid value of this ester was 1.0. The HLB value of polyglycerin laurate was 15.6.
- Polyglycerin palmitate was obtained from 175.0 g of Taiyo Kagaku's Great Oil # 1000 and 175.0 g of palmitic acid in exactly the same steps as in Synthesis Example 5.
- the acid value of this ester was 1.5.
- the HLB level of the polyglycerin palmitate ester was 9.5.
- polyglycerin of Production Example 1 was used instead of Taiyo Chemical's Great Oil # 1000. Otherwise, polyglycerin stearate ester was obtained by exactly the same steps as in Synthesis Example 5. The HLB value was 9.5.
- Polyglycerol oleate was obtained by exactly the same process as in Synthesis Example 5 using 168. O g of Taiyo Chemical's Great Oil # 1000 and 182.0 g of oleic acid. The acid value of this ester was 1.0. The HLB value of the polyglycerol oleate was 9.2.
- polyglycerin stearate was obtained in exactly the same steps as in Synthesis Example 5.
- the acid value of this ester was 1.0.
- the HLB value of polyglycerin stearate ester was 11.6.
- Polyglycerin stearate was obtained from 87.5 g of Taiyo Kagaku's Great Oil # 1000 and 262.5 g of stearic acid in exactly the same steps as in Synthesis Example 5. The acid value of this ester was 1.5. The HLB value of polyglycerin stearate ester was 4.0. '
- Polyglycerol laurate was obtained from 170. Og and 80. Og of lauric acid in Great Oil # 1000 manufactured by Taiyo Kagaku in exactly the same steps as in Synthesis Example 5. The acid value of this ester was 1.5. The HLB value of polyglycerin laurate was 9.5. Examples 1 to 8, Comparative Example:! ⁇ 12
- Emulsified cosmetics were prepared according to the formulations shown in Tables 1 and 2. That is, the polyglycerol fatty acid ester, higher alcohol and oily components are mixed and dissolved at 70 ° C under homomixer stirring (3000 rpm), and water or 70 ° C water or water, 1.3-butylene glycol is added thereto. The mixed solution of the above and other components were poured to perform phase inversion emulsification. Thereafter, an aqueous solution of sodium hydroxide was added, and an aqueous solution of Carbopol was added. The emulsion was cooled to 30 ° C and taken out, and allowed to stand at 25 ° C for 24 hours to obtain a cream.
- the mixing ratio of the hydrophilic polyglycerin fatty acid ester and the lipophilic polyglycerin fatty acid ester was selected such that the average particle size was minimized so that HLB could be matched. Only Comparative Example 11 excludes hydrophilic polyglycerol fatty acid esters because of their low HLB value).
- the average particle size was measured with a laser diffraction particle size distribution analyzer L A-5 ° 0 manufactured by Horiba, Ltd.
- Emulsion stability Stored at 45 ° C for 1 month, and confirmed whether oil separation and creaming did not occur. Stable ⁇ With trimming ⁇ Oil phase separation X X
- Viscosity at 25 ° C and 45 ° C immediately after production was measured with a BL type viscometer. The ratio of each viscosity was calculated and evaluated according to the following criteria.
- Burnish state during use A cherry-sized product was applied to the upper arm and disappeared smoothly, or time was measured with a stopwatch to determine.
- Synthesis example 7 0.2 0.5 0.6 Cetanol 2 2 2 2 2 1 2 2 Stearyl alcohol 1 1 2 Liquid raffin 20 20 20 20 20 10 20 20 Tri 2-ethylhexanoic acid
- FIG. 1 compares the viscosity of each of the cream of Example 1 and the cream of Comparative Example 1 at each temperature. From FIG. 1, it can be seen that the product of the present invention has little change in viscosity with respect to temperature.
- An emollient cream was prepared according to the following formulation. That is, (1) to (1 1) are mixed and dissolved at 75 ° C under homomixer stirring (5000 rpm), and the mixed solution of (1 2) to (14) at 75 ° C is poured therein. Phase inversion emulsification was performed. Thereafter, (15) was added, and (16) was added. The emulsion was cooled to 30 ° C and taken out, and allowed to stand at 25 ° C for 24 hours to obtain a lime.
- the evaluation method was the same as in Examples 1 to 8, the average particle size was 0.56 / im, the emulsification stability was ⁇ , and the change in hardness was ⁇ (viscosity: 25 ° C; 7020 OmPas, 45 ° C; 43,600 mPa ⁇ s), low-temperature stability: ((viscosity: 7100 OmPa as), appearance texture: ⁇ , and burnishing during use: ⁇ .
- An emollient cream was obtained in the same manner as in Example 9, except that the component (4) was replaced with soybean hydrogenated phospholipid (PC concentration: 60% by weight).
- the evaluation method was the same as in Examples 1 to 8, the average particle size was 0.50 ⁇ m, the emulsification stability was ⁇ , and the change in hardness was ⁇ (viscosity: 25 ° C; 7400 OmP a ⁇ s, 550 ° C; 49600 mPas), low-temperature stability was excellent (viscosity: 7550 mPas), the texture was ⁇ , and the burnishing property during use was ⁇ .
- An emulsion was prepared according to the following formulation. That is, (1) to (11) were mixed and dissolved at 65 ° C under blade stirring, and the mixed solution of (12) to (14) at 75 ° C was poured into the mixture and Phase emulsification was performed. Thereafter, (15) was added, and (16) was added. The emulsion was cooled to 30 ° C and taken out, and allowed to stand at 25 ° C for 24 hours to obtain an emulsion. Evaluation was performed in the same manner.
- the average particle size was 0.68 im, the emulsification stability was ⁇ , and the change in hardness was ⁇ (viscosity: 25 ° C; 862 OmPas, 45 ° C; 540 OmP a ⁇ s),
- the low-temperature stability was ((viscosity: 25 ° C; 888 OmP as), the appearance texture was ⁇ , and the burnishing property was ⁇ .
- An emulsion was obtained in the same manner as in Example 11, except that the component (6) was replaced with phytosteryl oleate.
- the evaluation method was the same as in Examples 1 to 8, the average particle size was 0.58 ⁇ m, the emulsification stability was ⁇ , and the change in hardness was ⁇ (viscosity: 25 ° C; 902 OmPas, 45 ° C; 636 OmPas), low-temperature stability was ⁇ (viscosity: 25 ° C; 8960 mPas), the appearance texture was ⁇ , and the finish was vanishing ⁇ .
- a UV cream was prepared according to the following formulation. That is, (1) to (: L1) are mixed and dissolved at 75 ° C under homomixer stirring (5000, rpm), and 75
- the mixed solution of (12) to (14) was poured to perform phase inversion emulsification. Then, (15) was added. The emulsion was cooled to 30 ° C and taken out, and allowed to stand at 25 ° C for 24 hours to obtain a cream.
- the evaluation method was the same as in Examples 1 to 8, but since the viscosity was 10,000 OmPa ⁇ s or more, a BH type viscometer was used. Average particle size is 0.88 ⁇ m, emulsification stability is ⁇ , hardness change is ⁇ (viscosity: 25 ° C; 24400 OmP a ⁇ s
- Example 11 In the composition of Example 1, the component (2) was composed of Taiyo Kagaku Sansoft Q-183Y (polyglycerin stearate, 111 ⁇ 8 value: 10.2; polyglycerin constituting the composition had an average degree of polymerization of 10, free Glycerin 3%, dimer component 5%, trimer component 7%, tetramer component 8%, pentamer component 9%, hexamer component 10%, heptamer component 12%, octamer (2% of body component, 12% of 9-mer component, 8% of 10-mer component, 5% of 11-mer component), and an emulsion was similarly obtained.
- Average particle size is 0.50 / _ (m, emulsification stability is ⁇ , change of hardness is ⁇ (viscosity: 25 ° C; 9000mPa's, 45 ° C; 6120mPa's
- Lotions were prepared according to the formulations shown in Tables 3 and 4. That is, a polyglycerin fatty acid ester, lecithin, and an oily component are mixed and dissolved at 70 ° C with a blade type stirrer, and a mixed solution of 70 ° C water, 1.3-butylene glycol, and other components is added thereto. After pouring, it was cooled to 30 ° C and taken out to obtain a lotion. The mixing ratio of the hydrophilic polyglycerin fatty acid ester and the lipophilic polyglycerin fatty acid ester was selected such that the average particle diameter was minimized so that HLB could be matched.
- esters and Comparative Example 19 are excluded because hydrophilic polyglycerol fatty acid esters have low HLB values).
- the average particle size was measured by COULTER COUNTER N-4.
- the transmittance was measured with JASCOV-570 manufactured by JASCO Corporation at a wavelength of 750 nm and a measurement optical path of 10 mm using purified water as a control.
- the pH was measured with a pH meter F-22 manufactured by Horiba, Ltd.
- Emulsion stability The emulsion was stored at 40 ° C for 1 month, and visually checked for oil separation and creaming. Stable _ ⁇ Tali-Mingu ⁇ Oil phase separation X
- Nisshin Oil “Basis LS-60 HRJ composition PC: 71%, PE: 11%, PI: ND%)
- An emollient lotion was prepared according to the following formulation. That is, 65 ° C With a blade-type stirrer, mix and dissolve (1) to (6), pour (7) to (9) at 65 ° C into it, cool to 30 ° C and take out to obtain a lotion .
- the evaluation method was the same as in Examples 9 to 18, the average particle size was 46.3 nm, the appearance was ⁇ , and the transmittance stability was ⁇ (immediately 83.6./oT, 83.2% after 1 month) , ⁇ ⁇ stability (6.34 immediately after, 6.25 one month later).
- Example 20 (emollient lotion)
- Example 19 In the formulation of Example 9, the component (7) was replaced with 1.3-butylendalcol, and the component (8) was replaced with 3-methyl-1,3-butylene glycol, and the others were the same as in Example 11. Got lotion. Evaluation method is according to Examples 9-18, average particle size is 48.3 nm, appearance is ⁇ , transmittance stability is ⁇ (85.3% T immediately after, 83.4% 85 after one month), ⁇ stable Sex (6.23 immediately after, 6.17 one month later).
- a lotion was obtained in the same manner as in Example 20, except that the component (3) was replaced with glyceryl monooleate in the formulation of Example 20.
- the average particle size was 52.3 nm, the appearance was ⁇ , and the transmittance was stable.
- X 82.0% T immediately after, 0% ⁇ one month later
- ⁇ stability (6.20 immediately after, 5.03 one month later).
- Example 21 ( ⁇ molient lotion) A lotion was obtained in the same manner as in Example 19 except that, in the composition of Example 19, the component (5) was replaced with phytosteryl oleate.
- the evaluation method was the same as in Examples 9 to 18, the average particle size was 40.3 nm, the appearance was ⁇ , the transmittance stability was ⁇ (immediately 91.3% T, one month later 99.1% ⁇ ), ⁇ stable Sex (immediately 6.26, one month later 6.25)
- a medicated beauty serum was prepared according to the following formulation. That is, (1) to (9) were mixed and dissolved at 65 ° C with a blade type stirrer, and (10) at 65 ° C was poured there. Thereafter, (11) and (12) were added, cooled to 30 ° C and taken out to obtain a serum. Evaluation method is according to Examples 9-18, average particle size is 74.3 nm, appearance is ⁇ , transmittance stability is ⁇ (immediately 81.5% T, one month later 80.7% ⁇ ), ⁇ stable The sex was ⁇ (6.13 immediately, 6.00 one month later).
- Nisshin Oil Refinery Basis L S—100 H Composition: PC: 97%, PE: N.D. P.I .: N.D.
- Example 17 In the formulation of Example 17, 1.8 g of the component (1) and 0.6 g of Sunsoft Q-183Y manufactured by Taiyo Kagaku Co., Ltd. (polyglycerin stearate, HLB value 10.2 : Constituent polyglycerin has an average degree of polymerization of 10, free glycerin 3%, dimer component 5%, trimer component 7%, tetramer component 8%, pentamer component 9%, hexamer Component 10%, 7-mer component 12%, octamer component 21%, 9-mer component 12%, 10-mer component 8%, 11-mer or higher component 5%), etc.
- a lotion was obtained in the same manner as in Example 17. Average particle size is 40. lnm, appearance is ⁇ , transmittance stability is ⁇ (immediately 8.8.3% T, one month later 88.1% ⁇ ), ⁇ ⁇ stability (immediately 6, 23, 1 month) 6.17).
- the present invention is an emulsified cosmetic and an external preparation containing a polyglycerin fatty acid ester as an emulsifying base, and can be used in the fields of cosmetics, quasi-drugs, pharmaceuticals, household goods and the like.
- a polyglycerin fatty acid ester with a high HLB value is used so as to be easily used in the phase inversion emulsification method to obtain the physical properties of higher alcohols and monoalkyl glyceryl ethers, it hardens at temperatures higher than 40 ° C. It is stable over time after storage, and it does not increase in hardness over time even at 0 ° C, is stable, has no water separation, and has good texture in appearance. It is possible to provide an emulsified cosmetic and an external preparation that can be smoothly panitished without leaving white on the skin when used.
- a cosmetic and an external preparation prepared by combining a polyglycerin fatty acid ester and a natural lecithin, which have been a problem in the past, over time.
- the problem of pH drop can be solved.
- the composition of the present invention can be obtained by an emulsification method other than the phase inversion emulsification method, for example, a dispersion emulsification method, a D-phase emulsification method, and a liquid crystal emulsification method. Unless the hardness is particularly required, the same effect can be obtained by these methods, so it can be said that the invention has a very wide application range.
- the present invention also provides a transparent emulsified cosmetic and an external preparation containing a polyglycerin fatty acid ester and lecithin as an emulsifying base, and can be used in the cosmetics, quasi-drugs, the pharmaceutical field, and household goods.
- An aqueous composition that uses a polyglycerin fatty acid ester and lecithin in combination, is transparent and emulsion-stable, without turbidity or separation of oily components, even without the addition of stabilizers such as thickeners. It is an excellent transparent emulsified cosmetic and external preparation which is stable with no decrease in pH over time and does not show precipitation of fatty acids or lecithin over time.
- the compounding amount of the oily component was set to a very high concentration, for example, 3 to 10% by weight in the composition as compared with the ethylene oxide type fine emulsion. Even in this case, it is transparent and stable, and can be applied to transparent cosmetics and external preparations with high emollient effects similar to emulsions and creams, which cannot be obtained with conventional lotions and lotions.
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EP02713266A EP1380278A4 (en) | 2001-03-29 | 2002-03-29 | COSMETIC EMULSION PREPARATION AND TOPICAL APPLICATION |
US10/473,309 US20040115161A1 (en) | 2001-03-29 | 2002-03-29 | Cosmetic emulsion preparation and agent for external use |
JP2002576917A JP4350378B2 (ja) | 2001-03-29 | 2002-03-29 | 乳化化粧料及び外用剤 |
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PCT/JP2002/003203 WO2002078650A1 (fr) | 2001-03-29 | 2002-03-29 | Preparation d'emulsion cosmetique et agent pour usage externe |
Country Status (4)
Country | Link |
---|---|
US (1) | US20040115161A1 (ja) |
EP (1) | EP1380278A4 (ja) |
JP (1) | JP4350378B2 (ja) |
WO (1) | WO2002078650A1 (ja) |
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US7687066B2 (en) | 2003-05-09 | 2010-03-30 | The Nisshin Oillio Group, Ltd. | Self emulsifying oily liquid cosmetic |
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US8242169B2 (en) | 2006-07-04 | 2012-08-14 | Showa Denko K.K. | Emulsion composition |
WO2012115053A1 (ja) * | 2011-02-21 | 2012-08-30 | 株式会社ナンバースリー | 毛髪用組成物 |
JP2013519633A (ja) * | 2010-02-12 | 2013-05-30 | エヴォニク ゴールドシュミット ゲーエムベーハー | ポリグリセロール部分エステルを含有する化粧料組成物 |
US8461214B2 (en) | 2004-01-06 | 2013-06-11 | Shiseido Co., Ltd. | One-phase microemulsion compositions, O/W ultrafine emulsion external formulations and method for producing the same |
JP5255749B2 (ja) * | 2003-09-05 | 2013-08-07 | 阪本薬品工業株式会社 | 化粧品用抱水性油性原料及び化粧品 |
JP2015003888A (ja) * | 2013-06-24 | 2015-01-08 | ポーラ化成工業株式会社 | 皮膚外用剤 |
JP2015003889A (ja) * | 2013-06-24 | 2015-01-08 | ポーラ化成工業株式会社 | 皮膚外用剤 |
JP2015199731A (ja) * | 2014-04-01 | 2015-11-12 | 株式会社ポーラファルマ | 皮膚外用剤の使用性の評価法及び該評価法で使用性に優れると判別される皮膚外用剤 |
JP2016008203A (ja) * | 2014-06-25 | 2016-01-18 | ロレアル | ナノエマルション若しくはマイクロエマルションの形態の又はラメラ構造を有する組成物 |
US10561587B2 (en) | 2014-04-01 | 2020-02-18 | L'oreal | Composition in the form of nano- or micro-emulsion |
JPWO2018211847A1 (ja) * | 2017-05-18 | 2020-02-27 | キユーピー株式会社 | 自己乳化性を有する組成物、及びその製造方法、並びにナノエマルション、及びその製造方法 |
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AU2007224366A1 (en) * | 2006-03-06 | 2007-09-13 | The Procter & Gamble Company | Lipophilic personal care composition |
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- 2002-03-29 WO PCT/JP2002/003203 patent/WO2002078650A1/ja not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
JPWO2002078650A1 (ja) | 2004-07-15 |
US20040115161A1 (en) | 2004-06-17 |
EP1380278A4 (en) | 2004-12-15 |
EP1380278A1 (en) | 2004-01-14 |
JP4350378B2 (ja) | 2009-10-21 |
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