WO2011071148A1 - 唇用化粧料 - Google Patents

唇用化粧料 Download PDF

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Publication number
WO2011071148A1
WO2011071148A1 PCT/JP2010/072231 JP2010072231W WO2011071148A1 WO 2011071148 A1 WO2011071148 A1 WO 2011071148A1 JP 2010072231 W JP2010072231 W JP 2010072231W WO 2011071148 A1 WO2011071148 A1 WO 2011071148A1
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Prior art keywords
mass
component
lip cosmetic
polyglyceryl
lip
Prior art date
Application number
PCT/JP2010/072231
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English (en)
French (fr)
Japanese (ja)
Inventor
友 大澤
智子 池田
善春 辻
智子 渡辺
希子 冨田
Original Assignee
株式会社 資生堂
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Priority claimed from JP2010160611A external-priority patent/JP4772157B1/ja
Priority claimed from JP2010160614A external-priority patent/JP4772158B2/ja
Application filed by 株式会社 資生堂 filed Critical 株式会社 資生堂
Priority to EP10836067.8A priority Critical patent/EP2510918B1/en
Priority to US13/514,309 priority patent/US20120269755A1/en
Priority to ES10836067.8T priority patent/ES2645713T3/es
Priority to RU2012126985/15A priority patent/RU2540906C2/ru
Priority to CN201080056129.4A priority patent/CN102781414B/zh
Publication of WO2011071148A1 publication Critical patent/WO2011071148A1/ja
Priority to HK13102211A priority patent/HK1175101A1/xx
Priority to US14/096,250 priority patent/US20140093462A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585Organosilicon compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06Lipsticks

Definitions

  • the present invention relates to a lip cosmetic, and more particularly to a lip cosmetic that has an excellent secondary adhesion-less effect immediately after application and has excellent durability and stability.
  • the conventional lip cosmetics have a problem of secondary adhesion in which after the lipstick is applied to the lips, the lipstick is transferred to a portion such as a cup that contacts the lips.
  • cosmetics for lips have been developed that have a so-called secondary adhesion-less effect that hardly causes secondary adhesion.
  • a volatile hydrocarbon solvent a non-volatile silicone compound that can be dissolved or dispersed in a volatile hydrocarbon solvent, and a non-volatile silicone compound that is incompatible with a non-volatile silicone compound dissolved in a volatile solvent.
  • Transfer-resistant cosmetic compositions are disclosed that contain a non-volatile hydrocarbon-based oil, the non-volatile hydrocarbon-based oil having certain solubility parameters.
  • Patent Document 2 describes a lipstick composition having transfer resistance containing a non-compatible perfluoropolyether-type non-volatile oil and a volatile oil.
  • the oil component is separated during application to the support, and the oil component moves on the first composition.
  • the first composition contains a considerable amount of wax and is in a solid state, the glossy and moist feeling cannot be sufficiently obtained. Further, in this system, it is difficult to disperse the incompatible oil phase satisfactorily, which causes stability problems such as sweating.
  • Patent Document 3 discloses a stick cosmetic product having a transfer resistance in which a silicone surfactant is blended in combination with a volatile oil component and a pigment is well dispersed.
  • this stick cosmetic has a large ratio in the composition of the volatile oil, it has a matte finish and has a disadvantage that it tends to cause a dry feeling on the lips.
  • Patent Document 4 discloses a one-phase lipstick composition containing a volatile oil and a silicone resin.
  • this lipstick composition has improved transfer resistance, a dry feeling tends to occur over time after the volatile oil evaporates, and a resin film remains on the lips, resulting in a feeling of film and tension.
  • the obtained deposit is a mat.
  • Patent Document 5 includes a continuous phase oil containing a silicone-based film agent, a volatile silicone-based oil, a non-volatile silicone-based liquid oil, and an emulsifier, and a dispersed phase oil containing an ester oil and a coloring material.
  • An oil-in-oil type emulsion composition having a blending ratio of phase oil content / (dispersed phase oil content + continuous phase oil content) of 0.05 to 0.5 is described.
  • this oil-in-oil type emulsion composition tends to cause uneven color because the coloring material is present in the dispersed phase, and furthermore, it may be difficult to maintain stability over time in this system.
  • the present invention has been made in view of the prior art, and provides a lip cosmetic that has an excellent secondary adhesion-less effect immediately after application, has a continuous gloss after application, and has excellent stability.
  • the purpose is to provide.
  • the lip cosmetic according to the present invention includes the following (a) and (b), and the blending amount of (b) is 20 to 70% by mass.
  • (B) (b1) Methylphenyl silicone 20 to 70% by mass
  • (b1) is not separated when mixed with (a) at 130 ° C. as a whole component (b1), but is separated by one or two or more when mixed with (a) at 25 ° C. It is preferable to consist of methylphenyl silicone.
  • the lip cosmetic preferably further comprises (c) 4 to 10% by mass of a wax. In the lip cosmetic, it is preferable that diphenylsiloxyphenyl trimethicone is contained in the component (b1).
  • the component (a) is preferably such that polyglyceryl isostearate having a polymerization degree of 5 is 40% by mass or more based on the total amount of the component (a).
  • the component (a) is preferably polyglyceryl-5 triisostearate.
  • the lip cosmetic according to the present invention includes the following (a) and (b), wherein the blending amount of (b) is 30 to 70% by mass.
  • B) (b1) Methylphenyl silicone 20-60% by mass
  • B2 Pentaerythritol ester 5 to 45% by mass
  • the lip cosmetic according to the present invention includes the following (a) to (c).
  • the component (a) polyglyceryl isostearate used in the present invention is a surfactant and is obtained by adding isostearic acid to a polyglycerin having an average addition mole number of 4 to 10 without specifying the location. Polyglycerin having an average added mole number of 5 is particularly preferable. Further, it is necessary to use 1 to 4 isostearic acid added in one molecule, and 2 to 4 are particularly preferable.
  • the component (a) encloses the coloring material due to the share at the time of application, and immediately separates from the component (b).
  • Polyglyceryl isostearate can be provided by various known synthetic methods, but those having a narrow distribution of the number of moles of glycerin added and those having a small number of cyclic substances as impurities are preferred. Such polyglyceryl isostearate is disclosed in, for example, Japanese Patent No. 34877881 and Japanese Patent Application Laid-Open No. 2006-111539 (polyglycerin having a hydroxyl value of 1200 or less and primary hydroxyl group of 50% or more of all hydroxyl groups and a fatty acid esterified. Manufactured polyglycerin fatty acid ester).
  • polyglyceryl isostearate having a polymerization degree of 5 is preferably 40% by mass or more based on the total amount of component (a).
  • the polyglyceryl-5 isostearate can be provided by various known synthetic methods.
  • polyglycerin-5 and polyglyceryl-5 isostearate obtained by using isostearic acid as a raw material with a low degree of polyglycerin and a narrow distribution of the degree of polymerization are preferred, and in particular, the degree of polymerization of glycerin is 5
  • the polyglyceryl-5 isostearate is preferably 40% by mass or more based on the total amount of component (a).
  • the isostearic acid residue is preferably 2-4, especially 3, polyglyceryl-5 triisostearate.
  • polyglycerol when polyglycerol is produced using glycerol as a raw material, many undesirable by-products such as intramolecular condensation, 6-membered ring and 8-membered ring are generated during dehydration condensation.
  • Polyglycerin obtained by synthesis and purification using glycidol, epichlorohydrin, monochlorohydrin or the like as a raw material is preferable so as not to be generated.
  • polyglycerin with fatty acids generally low molecular weight polyglycerin is more reactive with fatty acids than high molecular weight polyglycerin, so when using polyglycerin with a wide molecular weight distribution as a raw material A uniform ester cannot be produced.
  • polyglycerin having a molecular weight distribution as narrow as possible is preferable.
  • it can be obtained by a dehalogenated alkali metal salt reaction using glycerin or a partial alcoholate thereof and a halogenated hydrocarbon or oxyhalogenated hydrocarbon as raw materials.
  • the polyglyceryl-5 isostearate of the present invention is esterified with the polyglycerol obtained above and isostearic acid by a known method.
  • the esterification can be performed under an alkali catalyst, an acid catalyst, or in the absence of a catalyst under normal pressure or reduced pressure.
  • the blending amount of (a) polyglyceryl isostearate in the present invention is 5 to 20% by mass, preferably 12 to 20% by mass. If the amount of component (a) is too large or too small, the secondary adhesion-less effect is inferior, and if it is too large, stickiness tends to occur after application.
  • (B) methylphenyl silicone and / or pentaerythritol ester) (B) component used by this invention isolate
  • the methyl phenyl silicone which is the component (b1) is an essential component
  • the pentaerythritol ester which is the component (b2) is not an essential component.
  • by combining the component (b1) and the component (b2) it is possible to obtain a lip cosmetic that is more excellent in secondary adhesion-less effect and stability.
  • the methylphenyl silicone may be a single type or a mixture of two or more types.
  • the component (b1) is not separated as a whole component (b1) when mixed with the component (a) at 130 ° C., but mixed with the component (a) at 25 ° C. Those that sometimes separate are preferred.
  • methylphenyl silicone it is preferable to use trimethylpentaphenyltrisiloxane, diphenyldimethicone, diphenylsiloxyphenyltrimethicone. And it is preferable to mix
  • Examples of the trimethylpentaphenyltrisiloxane include methylphenyl silicone FZ3156 (165 mm2 / s (25 ° C.), manufactured by Toray Dow Corning) as a commercial product.
  • diphenyl dimethicone silicone KF54 (400 mm2 / s (25 ° C.), manufactured by Shin-Etsu Chemical Co., Ltd.), silicone KF50-300CS (manufactured by Shin-Etsu Chemical Co., Ltd.), silicone KF-54HV (manufactured by Shin-Etsu Chemical Co., Ltd.) and the like are listed as commercially available products.
  • Examples of diphenylsiloxyphenyl trimethicone include silicone KF56 (14 mm 2 / s (25 ° C.), manufactured by Shin-Etsu Chemical Co., Ltd.)).
  • phenyl trimethicone for example, silicone SH556 (22 mm2 / s (25 ° C.), manufactured by Toray Dow Corning)
  • silicone SH556 22 mm2 / s (25 ° C.), manufactured by Toray Dow Corning
  • the amount of methylphenyl silicone is 20 to 70% by mass, preferably 25 to 60% by mass, and particularly preferably 30 to 55% by mass.
  • the blending amount of the component (b1) is less than 20% by mass, secondary adhesion tends to occur and the gloss is small. Moreover, when it exceeds 70 mass%, stability will be bad.
  • diphenylsiloxyphenyl trimethicone is preferably included as the component (b1).
  • the amount of diphenylsiloxyphenyl trimethicone is preferably 10 to 50% by mass.
  • diphenylsiloxyphenyl trimethicone / ⁇ component (b1) other than diphenylsiloxyphenyl trimethicone) is used at 0.5 to 3.5 (mass ratio), and 1.2 to 2 (mass ratio). It is particularly preferable to use it.
  • diphenylsiloxyphenyl trimethicone / ⁇ component (b1) other than diphenylsiloxyphenyl trimethicone) 0.8 to 3.5 (mass ratio).
  • Pentaerythritol ester can be produced by a general synthesis method.
  • (di) pentaerythritol and an acid corresponding to the compound to be produced such as benzoic acid, 2-ethylhexanoic acid, behenic acid, etc. are put in a suitable reaction vessel (the order of addition is not particularly limited), and acid, alkali,
  • the reaction is carried out in the presence or absence of other metal catalyst, preferably in an organic solvent or / and a gas inert to the reaction while removing by-product water at 150 to 250 ° C. for several hours to 30 hours. It can be obtained by doing.
  • Examples of the pentaerythritol ester according to the present invention include tetra (benzoic acid / 2-ethylhexanoic acid) pentaerythritol, tetra (behenic acid / benzoic acid / 2-ethylhexanoic acid) pentaerythritol, and tetra-2-ethyl.
  • Examples include hexanoic acid pentaerythrit and hexa (12-hydroxystearic acid) dipentaerythlit.
  • Such pentaerythritol esters can be used alone or in combination of two or more.
  • liquid pentaerythritol ester can be suitably used because it is difficult to separate when the components (a) and (b1) are mixed at 130 ° C.
  • liquid pentaerythritol esters include tetra (benzoic acid / 2-ethylhexanoic acid) pentaerythritol and tetra-2-ethylhexanoic acid pentaerythritol.
  • the blending amount of pentaerythritol ester is 0 to 45% by mass, preferably 5 to 45% by mass, and particularly preferably 10 to 40% by mass. If the blending amount of the component (b2) is too small, secondary adhesion tends to occur or gloss may be reduced. Moreover, when there are too many compounding quantities, stability may worsen.
  • the amount of component (b) (the total amount of components (b1) and (b2)) is 20 to 70% by mass, preferably 50 to 70% by mass.
  • the blending amount of the component (b) is less than 20% by mass, secondary adhesion tends to occur and gloss is also reduced.
  • it exceeds 70 mass% stability will worsen.
  • ((C) wax) in addition to the above essential components, it is preferable to further add (c) a wax.
  • the wax is not particularly limited as long as it is usually blended in cosmetics, and examples thereof include carnauba wax, candelilla wax, bees wax, ceresin, microcrystalline wax, solid paraffin, molasses, and polyethylene wax.
  • the blending amount of the wax is preferably 4 to 10% by mass, more preferably 5 to 10% by mass, and particularly preferably 6 to 9% by mass. If the blending amount of the wax is too small, it may be difficult to solidify, and if it is too large, the spread may be heavy and the gloss may be lost.
  • ((D) Glycerin) In the present invention, it is preferable to further blend (d) glycerin.
  • the secondary adhesion-less effect is improved.
  • a part of polyglyceryl isostearate for example, 20 to 40% by mass in the total amount of component (a) is changed to glycerin to form an association structure, and the viscosity of the component that adheres to the lips is only component (a) It becomes higher than when using.
  • glycerin Since glycerin is used as a raw material in the production of polyglyceryl isostearate, it may be contained as an impurity of polyglyceryl isostearate and may not need to be added separately.
  • the lip cosmetic of the present invention includes oils, powders, polymer compounds, moisturizers, fragrances, antioxidants, antiseptics, and the like other than those used in normal lip cosmetics.
  • a cosmetic ingredient etc. can be suitably mix
  • an oil agent other than the components (b1) and (b2) it is preferable to blend an oil component that is compatible with the whole at 130 ° C.
  • An example of such an oil agent is isoparaffin.
  • an oil agent it is preferable that it is only the said component or an essential component, and does not contain another oil agent.
  • humectant examples include polyhydric alcohol humectants such as propylene glycol and 1,3 butylene glycol.
  • a coloring material can also be mix
  • the color material may be any color material that is usually used in cosmetics for lips, and may be in the form of powder or rake (a state in which oil is kneaded). It may be an inorganic pigment, an organic pigment, or a pearl agent. Since the color material is held in the component (a) and applied to the inside of the component (b) when the cosmetic is applied, it is difficult for the color material to adhere to the secondary material.
  • the blending amount of the coloring material is preferably 1 to 13% by mass, and particularly preferably 3 to 8% by mass.
  • a film agent can also be mix
  • the film agent include (alkyl acrylate / dimethicone) copolymer and the like.
  • silicone KP545 made by Shin-Etsu Chemical Co., Ltd.
  • the blending amount is preferably 2 to 15% by mass, particularly preferably 5 to 10% by mass.
  • the lip cosmetic of the present invention is preferably composed of components so as not to be separated in all of the production steps and to be in a uniform one-phase state. Specifically, the total composition is 130 ° C. It is preferable that the components are constituted so that they are not separated in a uniform one-phase state.
  • the lip cosmetic of the present invention can be applied to lipstick, lip gloss, lip base for base, lipstick overcoat, lip balm and the like.
  • Evaluation (1) Secondary adhesion-less effect An actual usability test was conducted with 10 specialist panels. The evaluation was a five-step sensory evaluation (score) for the secondary adhesion-less effect when the sample was applied to the lips, based on the following scoring criteria. Based on the average score, the following evaluation criteria were used.
  • Evaluation (2) Stability The color uniformity on the cut surface of the stick-shaped sample was evaluated according to the following evaluation criteria. (Evaluation criteria) A * : Uniform A: Uniform but poor color development B: Slightly non-uniform C: Non-uniform
  • Evaluation (3) Gloss An actual usability test was conducted with 10 professional panels. The evaluation was a five-step sensory evaluation (score) based on the following scoring criteria for the gloss when the sample was applied to the lips. Based on the average score, the following evaluation criteria were used.
  • Production Example 2 (Production of polyglyceryl-10 isostearate) A three-necked flask equipped with a thermometer, a Dimroth and a stirrer was charged with polyglycerin (Great Oil DE-1, decaglycerin; hydroxyl value 890, primary hydroxyl group ratio 46.6%, manufactured by Taiyo Kagaku Co., Ltd. 200 g of secondary hydroxyl group ratio 53.4%) and 600 ml of pyridine were added. To this, 370 g of chlorotriphenylmethyl (manufactured by Wako Pure Chemical Industries, Ltd.), which is a reagent that selectively reacts with a primary hydroxyl group, was added, stirred at 100 ° C.
  • polyglycerin Great Oil DE-1, decaglycerin; hydroxyl value 890, primary hydroxyl group ratio 46.6%, manufactured by Taiyo Kagaku Co., Ltd. 200 g of secondary hydroxyl group ratio 53.4%) and 600 ml of
  • the hydroxyl value was calculated in accordance with the 7th edition Food Additives Official “Fats and Fats Testing Method” or the Standard Oils and Fats Analysis Test Method.
  • the ratio between the primary hydroxyl group and the secondary hydroxyl group was determined by spectral analysis using a nuclear magnetic resonance apparatus. That is, using a nuclear magnetic resonance apparatus (13C-NMR) (manufactured by JEOL Ltd., JNM-A500), the ratio of primary hydroxyl groups and secondary hydroxyl groups of polyglycerol fractionated as described above was analyzed. 500 mg of the fractionated polyglycerol was dissolved in 2.8 ml of heavy water, and after filtration, 13C-NMR (125 MHz) spectrum was obtained by gated decoupling. The peak intensity is proportional to the carbon number by the gate decoupled measurement method.
  • 13C-NMR nuclear magnetic resonance apparatus
  • the 13C chemical shifts indicating the presence of primary hydroxyl groups and secondary hydroxyl groups are about 63 ppm for methylene carbon (CH 2 OH) and about 71 ppm for methine carbon (CHOH), respectively.
  • the ratio of secondary hydroxyl groups was calculated.
  • the methine carbon (CHOH) indicating the secondary hydroxyl group overlaps with the methylene carbon peak further adjacent to the methine carbon bonded to the methylene carbon indicating the primary hydroxyl group, and the integral value of itself cannot be obtained.
  • the integrated value was calculated from the signal intensity around 74 ppm of methylene carbon (CH2) adjacent to (CHOH).
  • the obtained polyglycerin-10 was reacted with isostearic acid by a conventional method to obtain polyglyceryl-10 isostearate in which the number of added moles of isostearic acid was changed.
  • the inventors of the present invention manufactured samples (lipsticks) having the composition shown in the following Tables 1 to 7 by a conventional method. Each sample was evaluated for the evaluation items (1) to (4) according to the above scoring criteria. The results are shown in Tables 1 to 7.
  • Test Examples 1-1 to 1-6 in which various polyglyceryl isostearates and various methylphenyl silicones were blended were excellent in secondary adhesion-less effect and stability, and had excellent gloss. According to Table 1 and studies by the present inventors, the polyglyceryl isostearate used in the present invention needs to have 4 to 10 moles of glycerin added and 1 to 4 isostearic acid residues. It is.
  • such polyglyceryl isostearate and methylphenyl silicone were the combination which does not isolate
  • diphenylsiloxyphenyl trimethicone / ⁇ component (b1) other than diphenylsiloxyphenyl trimethicone ⁇ 0.4 to 3.5 (Mass ratio) is preferred.
  • test Examples 5-1 to 5-7 and 3-7 in which the component (a), the component (b1), and the component (b2) are appropriately blended, are very excellent in the secondary adhesion-less effect, The gloss was also very good.
  • the ratio of diphenylsiloxytrimethicone in the component (b1) is preferably 0.8 or more.
  • the stability of the sample was inferior. Therefore, the blending amount of (b1) methylphenyl silicone blended in the lip cosmetic according to the present invention needs to be 20% by mass or more, and the blending amount of (b2) pentaerythritol ester needs to be 45% by mass or less. .
  • the lipsticks of Formulation Examples 5 to 7 shown below were all excellent in secondary adhesion-less effect, stability, and gloss.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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PCT/JP2010/072231 2009-12-11 2010-12-10 唇用化粧料 WO2011071148A1 (ja)

Priority Applications (7)

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EP10836067.8A EP2510918B1 (en) 2009-12-11 2010-12-10 Lip cosmetics
US13/514,309 US20120269755A1 (en) 2009-12-11 2010-12-10 Lip Cosmetics
ES10836067.8T ES2645713T3 (es) 2009-12-11 2010-12-10 Cosmética labial
RU2012126985/15A RU2540906C2 (ru) 2009-12-11 2010-12-10 Косметическое средство для губ
CN201080056129.4A CN102781414B (zh) 2009-12-11 2010-12-10 唇用化妆品
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JP2012149040A (ja) * 2010-12-28 2012-08-09 Kao Corp 口唇化粧料
JP2015107926A (ja) * 2013-12-04 2015-06-11 花王株式会社 口唇化粧料
JP2015520117A (ja) * 2012-06-21 2015-07-16 ロレアル 炭化水素系樹脂、炭化水素系ブロックコポリマー、不揮発性フェニルジメチコン油及び不揮発性炭化水素化油を含む化粧用組成物
US10071045B2 (en) 2012-06-21 2018-09-11 L'oreal Cosmetic composition comprising a hydrocarbonated-based resin, a hydrocarbon-based block copolymer, a non volatile dimethicone oil and a non volatile hydrocarbonated oil
JP2019167325A (ja) * 2018-03-26 2019-10-03 ポーラ化成工業株式会社 皮膚外用組成物
WO2020075875A1 (en) 2018-10-10 2020-04-16 K.K. Chanel Research And Technology Development Laboratory Lip cosmetic composition and use thereof

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US20190083379A1 (en) * 2017-09-18 2019-03-21 Mast Industries (Far East) Limited Gloss lip balm formulation
EP4333795A1 (en) * 2021-04-30 2024-03-13 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials

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JP2012149040A (ja) * 2010-12-28 2012-08-09 Kao Corp 口唇化粧料
JP2015520117A (ja) * 2012-06-21 2015-07-16 ロレアル 炭化水素系樹脂、炭化水素系ブロックコポリマー、不揮発性フェニルジメチコン油及び不揮発性炭化水素化油を含む化粧用組成物
US10071045B2 (en) 2012-06-21 2018-09-11 L'oreal Cosmetic composition comprising a hydrocarbonated-based resin, a hydrocarbon-based block copolymer, a non volatile dimethicone oil and a non volatile hydrocarbonated oil
JP2015107926A (ja) * 2013-12-04 2015-06-11 花王株式会社 口唇化粧料
JP2019167325A (ja) * 2018-03-26 2019-10-03 ポーラ化成工業株式会社 皮膚外用組成物
JP7089386B2 (ja) 2018-03-26 2022-06-22 ポーラ化成工業株式会社 皮膚外用組成物
WO2020075875A1 (en) 2018-10-10 2020-04-16 K.K. Chanel Research And Technology Development Laboratory Lip cosmetic composition and use thereof

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RU2012126985A (ru) 2014-01-20
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EP2510918B1 (en) 2017-09-20
US20120269755A1 (en) 2012-10-25
CN102781414B (zh) 2014-10-22
RU2540906C2 (ru) 2015-02-10
EP2510918A1 (en) 2012-10-17
KR20120102069A (ko) 2012-09-17
TWI482638B (zh) 2015-05-01
CN102781414A (zh) 2012-11-14
EP2510918A4 (en) 2015-07-08
US20140093462A1 (en) 2014-04-03

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