WO2016098747A1 - 水中油型乳化組成物 - Google Patents

水中油型乳化組成物 Download PDF

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Publication number
WO2016098747A1
WO2016098747A1 PCT/JP2015/084991 JP2015084991W WO2016098747A1 WO 2016098747 A1 WO2016098747 A1 WO 2016098747A1 JP 2015084991 W JP2015084991 W JP 2015084991W WO 2016098747 A1 WO2016098747 A1 WO 2016098747A1
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Prior art keywords
fatty acid
oil
dextrin
acid
mol
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PCT/JP2015/084991
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English (en)
French (fr)
Japanese (ja)
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健太郎 吉川
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株式会社コーセー
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Priority to JP2016564851A priority Critical patent/JP6744823B2/ja
Priority to CN201580068986.9A priority patent/CN106999359A/zh
Publication of WO2016098747A1 publication Critical patent/WO2016098747A1/ja

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • 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
    • A61K8/60Sugars; Derivatives 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • 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
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the present invention relates to an oil-in-water emulsion composition containing a specific dextrin fatty acid ester, an ester of a fatty acid having 8 to 18 carbon atoms and a monohydric alcohol having 2 to 16 carbon atoms, and polyoxyethylene hydrogenated castor oil.
  • the present invention relates to an oil-in-water emulsified composition having excellent non-stickiness, smoothness after finishing, and excellent stability over time.
  • hair cosmetics for treatments such as rinses and conditioners are desired to have higher conditioning effects such as a smooth finish, suppleness, and emollient.
  • Various techniques have been disclosed. For example, using a cationic polymer or a silicone derivative to enhance the finish flexibility (for example, see Patent Documents 1 to 3), or using a hydrocarbon oil to impart an emollient feeling to the finish (for example, , See Patent Document 4).
  • dextrin fatty acid esters having a high proportion of branched saturated fatty acids are blended in lipsticks, eyeliners, mascaras, foundations and the like as materials having excellent adhesion (tackiness) (see, for example, Patent Document 5).
  • the above-described cosmetic is an aspect of an oil-in-water emulsion composition
  • the conventional technology is smooth but not sticky regardless of the hair application, and it is smooth and supple after use. It was difficult to obtain an oil-in-water emulsion composition excellent in thickness.
  • an oil agent that coats the hair surface as a component that contributes to the smoothness after finishing in hair cosmetics and that can give a moist feeling is important.
  • various oil agents liquid oil, solid oil, resin, wax, etc.
  • dextrin fatty acid esters having a high proportion of branched fatty acids and being hydrophobized are particularly useful. Since the dextrin fatty acid ester is a material having a high adhesion (tackiness), it sometimes feels sticky during use. However, the fatty acid having 8 to 18 carbon atoms and a monohydric alcohol having 2 to 16 carbon atoms are sometimes used.
  • the present invention The following components (A) to (C); (A) Esterified product of dextrin and fatty acid, wherein the average polymerization degree of glucose of dextrin is 3 to 150, and fatty acid is one or more of branched saturated fatty acids having 4 to 26 carbon atoms.
  • linear saturated fatty acid having 2 to 22 carbon atoms linear or branched unsaturated fatty acid having 6 to 30 carbon atoms and cyclic saturated or unsaturated having 6 to 30 carbon atoms
  • An oil-in-water emulsion composition containing polyoxyethylene hydrogenated castor oil is provided. It is intended to.
  • an oil-in-water emulsion composition in which the branched saturated fatty acid constituting the dextrin fatty acid ester of component (A) is one or more selected from branched saturated fatty acids having 12 to 22 carbon atoms.
  • An oil-in-water emulsion composition in which the dextrin fatty acid ester of the component (A) is a dextrin fatty acid ester that does not gel a liquid paraffin having a kinematic viscosity of 8 mm 2 / s at 40 ° C. according to ASTM D445 measurement method. is there.
  • the component (A) dextrin fatty acid ester is a light fluid isoparaffin solution containing 40% by mass of a dextrin fatty acid ester formed on a glass plate with a 400 ⁇ m-thick applicator, and dried to a film of 100 g using a texture analyzer.
  • an oil-in-water emulsion composition which is a dextrin fatty acid ester having a load change (maximum stress value) applied to a contact point of 30 to 1000 g when a load is applied and held at 0.5 mm / second after holding for 10 seconds. It is.
  • an oil-in-water emulsion composition in which the component (C) polyoxyethylene hydrogenated castor oil is a polyoxyethylene hydrogenated castor oil having an HLB in the range of 6 to 13.
  • an oil-in-water emulsion composition in which the content ratio (B) / (A) of the component (A) to the component (B) is in the range of 1 to 100.
  • the present invention provides an oil-in-water emulsion composition containing a hydrocarbon that is liquid at 25 ° C. as component (D).
  • An oil-in-water emulsified composition having an average particle diameter of emulsified droplets of 500 nm or less is provided.
  • An oil-in-water emulsion composition used by spraying in a mist form is provided.
  • an oil-in-water emulsified composition that is a cosmetic for hair.
  • an oil-in-water emulsion composition which is excellent in non-stickiness, smoothness after finishing, and excellent in stability over time.
  • the component (A) dextrin fatty acid ester used in the oil-in-water emulsified composition of the present invention is an esterified product of dextrin and fatty acid, and the average polymerization degree of glucose of dextrin is 3 to 150.
  • the component (A) dextrin fatty acid ester used in the present invention has the following characteristics.
  • Liquid oil does not gel means that when liquid paraffin having a kinematic viscosity of 8 mm 2 / s at 40 ° C. according to ASTM D445 measurement method is used as a liquid oil, 5% by mass of dextrin fatty acid ester (hereinafter, simply “%”).
  • % 5% by mass of dextrin fatty acid ester
  • the viscosity was Yamaco DIGITAL VISCOMATE viscometer VM-100A (vibration type) (manufactured by Yamaichi Electronics Co., Ltd.) Is below the detection limit.
  • Yamaco DIGITAL VISCOMATE viscometer VM-100A vibration type
  • it can confirm by detecting a viscosity.
  • the film formed by the dextrin fatty acid ester has a specific range of adhesion (tackiness).
  • the “tackiness” is determined by applying the dextrin fatty acid ester to a support and bringing the other support into surface contact from a state where they are separated from each other, then retracting them and separating them.
  • a load change maximum stress value
  • a light liquid isoparaffin solution containing 40% of the dextrin fatty acid ester is formed on a glass plate with a 400 ⁇ m-thick applicator and dried.
  • Texture analyzer for example, texture analyzer TA.
  • a probe made of a 12.5 mm diameter cylindrical polyacetal resin manufactured by Delrin (registered trademark) DuPont was used as a probe, and a load of 100 g was applied after 10 seconds.
  • the load change when separated at 5 mm / sec, that is, the tackiness is 30 to 1,000 g.
  • the dextrin used for the component (A) dextrin fatty acid ester is preferably a dextrin having a glucose average polymerization degree of 3 to 150, particularly 10 to 100.
  • the average degree of polymerization of glucose is 2 or less, the obtained dextrin fatty acid ester becomes wax-like and the solubility in an oil agent decreases.
  • the average degree of polymerization of glucose exceeds 150, there may be a problem that the temperature for dissolving the dextrin fatty acid ester in the oil becomes high or the solubility becomes poor.
  • the sugar chain of dextrin may be linear, branched or cyclic.
  • the fatty acid used in the component (A) dextrin fatty acid ester is essentially one or two or more of branched saturated fatty acids having 4 to 26 carbon atoms, and further is a linear saturated fatty acid having 2 to 22 carbon atoms, carbon One or more selected from the group consisting of straight-chain or branched unsaturated fatty acids having 6 to 30 and cyclic saturated or unsaturated fatty acids having 6 to 30 carbon atoms (hereinafter referred to as those having 4 to 26 carbon atoms) When the fatty acids other than the branched saturated fatty acid are collectively represented, they may be referred to as “other fatty acids”.
  • the (A) dextrin fatty acid ester of the present invention is composed of only branched saturated fatty acids having 4 to 26 carbon atoms, or only branched saturated fatty acids having 4 to 26 carbon atoms and other fatty acids.
  • the composition ratio of the fatty acid in the component (A) dextrin fatty acid ester is such that one or more of the branched saturated fatty acids having 4 to 26 carbon atoms is more than 50 mol% and not more than 100 mol% with respect to the total fatty acids. Is 55 mol% or more and 100 mol% or less, and other fatty acids are 0 mol% or more and less than 50 mol%, preferably 0 mol% or more and 45 mol% or less.
  • Examples of the branched saturated fatty acid having 4 to 26 carbon atoms include isobutyric acid, isovaleric acid, 2-ethylbutyric acid, ethylmethylacetic acid, isoheptanoic acid, 2-ethylhexanoic acid, isononanoic acid, isodecanoic acid, isotridecanoic acid, iso Examples include myristic acid, isopalmitic acid, isostearic acid, isoarachidic acid, isohexacosanoic acid, and the like, and one or more of these can be appropriately selected or used in combination.
  • isostearic acid means one kind of branched stearic acid or a mixture of two or more kinds.
  • isostearic acid means one kind of branched stearic acid or a mixture of two or more kinds.
  • 5,7,7-trimethyl-2- (1,3,3-trimethylbutyl) -octanoic acid is converted to a branched aldehyde having 9 carbons by oxo reaction of isobutylene dimer, and then carbon is obtained by aldol condensation of this aldehyde.
  • the branched unsaturated aldehyde of formula 18 can be produced by hydrogenation and oxidation (hereinafter abbreviated as “aldol condensation type”), which is commercially available, for example, from Nissan Chemical Industries.
  • 2-Heptylundecanoic acid can be produced by dimerizing nonyl alcohol by a gerbet reaction (also referred to as Guerbet reaction or Gerbe reaction) and oxidizing it, which is commercially available from, for example, Mitsubishi Chemical Corporation.
  • a slightly different similar mixture is commercially available from Nissan Chemical Industries, Ltd., and a methyl branched type where the starting alcohol is not linearly saturated is also commercially available from Nissan Chemical Industries (hereinafter referred to as “gerbet reaction type” in general). (Omitted).
  • methyl-branched isostearic acid is obtained as a by-product at the time of dimer production of oleic acid, for example [for example, J. Org. Amer. Oil Chem. Soc. 51, 522 (1974)], for example, commercially available from Emery, Inc. of the United States (hereinafter referred to as “emery type”).
  • emery type Further starting materials of dimer acid which is a starting material of emery type isostearic acid may include not only oleic acid but also linoleic acid, linolenic acid and the like. In the present invention, this emery type is particularly preferable.
  • examples of the linear saturated fatty acid having 2 to 22 carbon atoms include acetic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearin.
  • An acid, arachidic acid, behenic acid, etc. are mentioned, These 1 type (s) or 2 or more types can be selected or used in combination suitably. Among these, those having 8 to 22 carbon atoms are preferable, and those having 12 to 22 carbon atoms are particularly preferable.
  • the linear or branched unsaturated fatty acid having 6 to 30 carbon atoms includes, for example, cis-4-decene (obtusil) as the monoene unsaturated fatty acid.
  • Acid 9-decene (caprolein) acid, cis-4-dodecene (Lindell) acid, cis-4-tetradecene (Tuzu) acid, cis-5-tetradecene (ficeterin) acid, cis-9-tetradecene (myristolein) ) Acid, cis-6-hexadecenoic acid, cis-9-hexadecene (palmitolein) acid, cis-9-octadecene (oleic) acid, trans-9-octadecenoic acid (elaidic acid), cis-11-octadecene (asclepine) acid Cis-11-eicosene (gondrain) acid, cis-17-hexacosene (ximene) acid, And polyene unsaturated fatty acids such as sorbic acid, linoleic acid, hiragoic
  • Examples include arachidonic acid, eicosapentaenoic acid, sardine acid, docosahexaenoic acid, nisinic acid, stearolic acid, crepenic acid, and xymenic acid.
  • cyclic saturated or unsaturated fatty acids having 6 to 30 carbon atoms are saturated having 6 to 30 carbon atoms having a cyclic structure in at least a part of the basic skeleton.
  • an unsaturated fatty acid such as 9,10-methylene-9-octadecenoic acid; allelelic acid, allepric acid, gollulinic acid, ⁇ -cyclopentylic acid, ⁇ -cyclohexylic acid, ⁇ -cyclopentylethylic acid, ⁇ -cyclohexylmethylic acid , ⁇ -cyclohexyl acid, 5 (6) -carboxy-4-hexyl-2-cyclohexene-1-octanoic acid, malvalic acid, sterlic acid, hydnocarpinic acid, and sorghumulinic acid.
  • unsaturated fatty acid such as 9,10-methylene-9-octadecenoic acid
  • allelelic acid allepric acid
  • gollulinic acid ⁇ -cyclopentylic acid
  • ⁇ -cyclohexylic acid ⁇ -cyclopentylethylic acid
  • examples of the component (A) dextrin fatty acid ester using a branched saturated fatty acid alone as the fatty acid include the following.
  • examples of the component (A) dextrin fatty acid ester when a mixed fatty acid of a branched saturated fatty acid and another fatty acid is used as the fatty acid include the following.
  • the substitution degree of fatty acid to dextrin of component (A) dextrin fatty acid ester is 1.0 to 3.0 per glucose unit, preferably 1.2 to 2.8.
  • the degree of substitution is less than 1.0, the dissolution temperature in liquid oil or the like is as high as 100 ° C. or higher, and coloring or a specific odor is not preferable.
  • Dextrin having an average degree of polymerization of glucose of 3 to 150, and one or more of branched saturated fatty acid derivatives having 4 to 26 carbon atoms, more than 50 mol% and not more than 100 mol% with respect to all fatty acid derivatives, and 1 selected from the group consisting of linear saturated fatty acid derivatives having 2 to 22 carbon atoms, linear or branched unsaturated fatty acid derivatives having 6 to 30 carbon atoms and cyclic saturated or unsaturated fatty acid derivatives having 6 to 30 carbon atoms.
  • Species or two or more kinds are reacted with a fatty acid derivative containing 0 mol% or more and less than 50 mol% with respect to the total fatty acid derivatives.
  • examples of the fatty acid derivative used for the esterification reaction with the dextrin include halides and acid anhydrides of the fatty acid.
  • dextrin is dispersed in a reaction solvent, and a catalyst is added as necessary.
  • the above-mentioned fatty acid halide, acid anhydride or the like is added and reacted.
  • these fatty acid derivatives are mixed and added and reacted at the same time.
  • the production method (2) first, a branched saturated fatty acid derivative having low reactivity is reacted, and then the others. The fatty acid derivative is added and reacted.
  • reaction solvent a solvent such as formamide such as dimethylformamide and formamide; acetamide; ketone; aromatic compounds such as benzene, toluene and xylene; and a solvent such as dioxane can be used as appropriate.
  • reaction catalyst tertiary amino compounds such as pyridine and picoline can be used.
  • the reaction temperature is appropriately selected depending on the starting fatty acid and the like, but a temperature of 0 ° C. to 100 ° C. is preferred.
  • component (A) in the present invention for example, Unifilma HVY (manufactured by Chiba Flour Milling) and the like can be mentioned.
  • the content of the component (A) dextrin fatty acid ester used in the oil-in-water emulsion composition of the present invention is not particularly limited, but is preferably 0.02 to 10%, more preferably 0.03 to 5%. Preferably, 0.03 to 1% is particularly preferable. Within this range, an oil-in-water emulsion composition that is excellent in smoothness of finish and excellent in non-stickiness is preferable.
  • the component (A) dextrin fatty acid ester of the present invention is an excellent one that exhibits a high conditioning effect even if it is a very small amount of blending or a rinse-type product that uses in bath.
  • Component (B) of the present invention is an ester of a fatty acid having 8 to 18 carbon atoms and a monohydric alcohol having 2 to 16 carbon atoms. In the present invention, it is particularly preferable not only for excellent compatibility with the component (A) but also for improving the non-stickiness.
  • the component (B) is an ester of a fatty acid having 8 to 18 carbon atoms and a monohydric alcohol having 2 to 16 carbon atoms. More preferably, the fatty acid of the component (B) has 9 to 16 carbon atoms. 9 to 14 are particularly preferable. For monohydric alcohols, 3 to 8 carbon atoms are more preferable, and 3 to 6 are particularly preferable. By using an ester in which a fatty acid having a more preferable carbon number and a monohydric alcohol are combined, it is preferable in terms of hair suppleness.
  • Such a component (B) is not particularly limited as long as it is used for ordinary cosmetics. Specifically, octyl octoate, palmityl octoate, isononyl isononanoate, isotridecyl isononanoate, ethyl laurate, octyl laurate hexyl octylate, ethyl myristate, butyl myristate, isopropyl myristate, ethyl palmitate, palmitic acid
  • Examples thereof include isopropyl, octyl palmitate, isopropyl oleate, ethyl oleate and the like, and these can be used alone or in combination.
  • Component (B) is particularly preferably isononyl isononanoate, isotridecyl isononanoate, ethyl oleate, isopropyl myristate, cetyl ethyl hexanoate, and ethyl hexyl palmitate, and most preferably isopropyl myristate.
  • component (B) in the present invention examples include, for example, Saracos 99, 816, 913, P-8 (Nisshin Oilio), CRODAMOL TN-LQ (CRODA, Japan), PALMESTER 1543 ( PALM OLEO), IPM-EX (Nippon Surfactant Kogyo Co., Ltd.) and the like.
  • the content of component (B) in the present invention is not particularly limited, but is preferably 0.02 to 20%, more preferably 0.03 to 10%, and particularly preferably 0.03 to 5%. Furthermore, 0.05 to 1% is preferable. By setting it within this range, it is possible to obtain an oil-in-water emulsion composition that is excellent not only in stickiness but also in smoothness after finishing.
  • the inclusion of the above-described component (A) and component (B) has more excellent effects such as a smooth finish, but the content ratio of these is set to a specific range. As a result, the effect can be further enhanced.
  • the content ratio by mass of the component (A) and the component (B) is not particularly limited, but is preferably 1 to 100 as the component (B) / component (A).
  • the range of is more preferable. If it is this range, since smoothness is maintained, there is no stickiness and it is excellent in a unity feeling and flexibility, it is more preferable.
  • the component (C) polyoxyethylene hydrogenated castor oil used in the present invention is a surfactant used for emulsification, and the component (C) contains the oil-in-water emulsion composition of the present invention.
  • the effect of improving the temporal stability can be obtained.
  • the component (C) is not particularly limited as long as it is usually used in cosmetics, but polyoxyethylene hydrogenated castor oil having an HLB in the range of 6 to 13 is more preferable.
  • polyoxyethylene (40E.O.) Hardened castor oil (HLB12.5) can be mentioned, and one or more kinds can be appropriately selected and used as necessary.
  • the calculated HLB value (weighted average value) may be included in the above 6 to 13, but it is more preferable that the calculated value of HLB alone is included in this range. In particular, it is preferable that everything is included in this range.
  • the medium HLB type among polyoxyethylene hydrogenated castor oils the emulsified droplets can be made fine and useful as an emulsifier.
  • component (C) in the present invention examples include, for example, EMALEX® HC-10, 20, 20 (Nihon Emulsion), NIKKOL HCO-10, 20, 40 (Nikko Chemicals), Uni Ox HC-20, 40 (manufactured by NOF Corporation), Marpon HC-40A (manufactured by Matsumoto Yushi Seiyaku Co., Ltd.) and the like.
  • component (C) in the present invention is not particularly limited, but is preferably 0.003 to 5%, more preferably 0.005 to 2.5%, and particularly preferably 0.005 to 1%. preferable. By setting it within this range, an oil-in-water emulsion composition that is preferable in terms of stability over time and excellent in non-stickiness can be obtained.
  • the present invention is an oil-in-water emulsion composition obtained by containing the components (A) to (C) described above, but it is also possible to contain a liquid hydrocarbon at 25 ° C. as the component (D). It is.
  • Component (D) contributes to the stability of emulsified droplets as an oil to be emulsified in an oil-in-water emulsified composition. By containing this, component (B) is compatible with component (B) and the emulsified droplets are refined. However, it is preferable in terms of stability over time.
  • Such component (D) is not particularly limited, and the origin of animal oil, vegetable oil, synthetic oil or the like is not limited.
  • hydrocarbons such as liquid paraffin, light liquid isoparaffin, dodecane, isododecane, tetradecane, isotetradecane, hexadecane, isohexadecane, squalane, plant squalane, polyisobutylene, polybutene, etc. Species or two or more can be used. Among these, hydrocarbon oils having a molecular weight of 200 to 800 are preferable, and isododecane, isotetradecane, isohexadecane, squalane and the like are more preferable in terms of stability over time.
  • component (B) is generally prone to Ostwald ripening and is not highly stable when emulsified due to creaming or the like.
  • a non-polar oil agent By combining such a non-polar oil agent, it is considered that Ostwald ripening can be effectively suppressed and stability over time is improved.
  • the content of the component (D) in the present invention is not particularly limited, but is preferably 0.0001 to 1%, more preferably 0.001 to 0.1%. By setting it within this range, it is possible to obtain an oil-in-water emulsion composition that not only has excellent stability over time but also has no stickiness.
  • component (D) in the present invention examples include, for example, Pearl Ream 4 (manufactured by NOF Corporation), purified polybutene HV-100F (SB) (manufactured by Nippon Natural Products), Nippon Oil Polybutene HV-35 / HV- 100 (above, manufactured by JX Nikko Nisshin Energy Co., Ltd.), Nom Coat HP30 / HP100 (above, manufactured by Nisshin Oillio Group), KLEAROL WHITE MINEAL OIL (made by SONNEBORN), IP Solvent 2028MU (made by Idemitsu Kosan Co., Ltd.), Chloratum LES Examples include SQUALANE (manufactured by Croda Japan Co., Ltd.) (manufactured by Kishimoto Special Liver Oil Industry Co., Ltd.), refined olive squalane (manufactured by Nikko Chemicals), and the like.
  • SQUALANE manufactured by Croda Japan Co.,
  • the present invention contains water as an oil-in-water emulsion composition.
  • the water here is not particularly limited as long as it is usually used in cosmetics. Specifically, purified water, hot spring water, deep water, or plant steam distilled water may be used, and one or more kinds may be appropriately selected and used as necessary.
  • the blending amount is not particularly limited, and can be blended as appropriate according to the amount of other components, but it can be generally used in the range of 20 to 99.9%, preferably 20 to 90%.
  • an oil-in-water emulsion composition can be obtained by using the component (C) described above, but in addition to the component (C), a cationic surfactant can be further contained.
  • a cationic surfactant is a component that can be expected to have a conditioning effect on hair, and is not particularly limited as long as it is a cationic surfactant that can be generally used in cosmetics.
  • the content of the cationic surfactant in the oil-in-water emulsion composition of the present invention is not particularly limited, but is preferably 0.01 to 10%, more preferably 0.1 to 5%. If it is in this range, cosmetics will be stable, and those with better usability will be obtained.
  • a phosphocholine group-containing polymer can be further used.
  • the phosphocholine group-containing polymer is not particularly limited as long as it has a phosphorylcholine group.
  • a phosphocholine group-containing polymer has properties derived from a phospholipid-like structure derived from a biological membrane, so when used in cosmetics, it has a moisturizing effect on the skin and a film-forming effect on the hair. A hair repair effect based on the above is expected.
  • the phosphocholine group-containing polymer is selected from a homopolymer of 2-methacryloyloxyethyl phosphorylcholine (MPC) and a copolymer of 2-methacryloyloxyethyl phosphorylcholine and a hydrophobic monomer.
  • MPC 2-methacryloyloxyethyl phosphorylcholine
  • a copolymer of 2-methacryloyloxyethyl phosphorylcholine and a hydrophobic monomer One type or two or more types can be given.
  • it does not specifically limit as a phosphocholine group containing polymer contained in this invention,
  • a weight average molecular weight is 5000 or more, and 10,000 or more are more preferable.
  • the type of the hydrophobic monomer is not particularly limited, but is preferably styrene, acrylic acid ester, or methacrylic acid ester.
  • the weight average molecular weight of the copolymer with the hydrophobic monomer is also preferably 5000 or more, and more preferably 10,000 or more.
  • the constituent molar ratio of MPC and hydrophobic monomer is preferably in the range of 50:50 to 97: 3.
  • the content of the phosphocholine group-containing polymer in the present invention is not particularly limited, but is preferably 0.001 to 5%, more preferably 0.005 to 1%, and 0.01 to 0.5%. Is more preferable. By setting it within this range, an oil-in-water emulsion composition excellent in the sustaining effect without stickiness can be obtained, which is preferable.
  • Examples of commercially available phosphocholine group-containing polymer components include, for example, LIPIDURE-HM, LIPIDURE-HM-500, LIPIDURE-HM-600 (all manufactured by NOF Corporation), MPC and butyl methacrylate as MPC homopolymers. And LIPIDURE-PMB, LIPIDURE A, LIPIDURE C, LIPIDURE-NA, LIPIDURE-NR, and LIPIDURE-S (all manufactured by NOF Corporation).
  • the method for producing the oil-in-water emulsion composition of the present invention is not particularly limited and is prepared by a conventional method.
  • the oil-based section containing the component (A) and the component (B) is heated and dissolved. Are mixed and stirred using a mixer or the like, and cooled to room temperature.
  • it can be set as the oil-in-water emulsion composition which is excellent in emulsification stability by adding and mixing a component (C) at the time of mixing and stirring.
  • Ingredient (C) may be mixed in either the aqueous section or the oil section.
  • oil-in-water emulsion composition of the present invention in addition to the above-mentioned components, in the quantitative and qualitative range that does not impair the effects of the present invention depending on the purpose, ordinary cosmetics and quasi drugs, Ingredients used in preparations such as external medicines, alcohols, powders for touch adjustment or coloring, general-purpose ingredients such as surfactants, water-soluble polymers, film forming agents, pearlescent agents, metal soaps, Oily gelling agent, resin, clathrate compound, moisturizer, antibacterial / preservative, deodorant, salt, pH adjuster, UV absorber, antioxidant, chelating agent, anti-fading agent, antifoaming agent, cooling agent , Cosmetic ingredients, propellants, fragrances, pigments and the like.
  • general-purpose ingredients such as surfactants, water-soluble polymers, film forming agents, pearlescent agents, metal soaps, Oily gelling agent, resin, clathrate compound, moisturizer, antibacterial / preservative, deodorant, salt, pH adjuster, UV absorber,
  • the oil-in-water emulsion composition of the present invention is not particularly limited, but those having an average particle diameter of emulsified droplets of 500 nm or less are particularly preferred. If it is this range, it will be hard to raise
  • the average particle size of the emulsified droplets in the present invention is a value measured using a laser diffraction / scattering particle size distribution measuring device (Laser diffraction / scattering particle size distribution measuring device LA-910 manufactured by Horiba, Ltd.).
  • the oil-in-water emulsion composition of the present invention can be applied as a skin external preparation such as an external gel, cream, ointment, liniment, lotion, haptic, and plaster.
  • the oil-in-water emulsion composition of the present invention can be applied as a cosmetic.
  • skin care cosmetics such as lotion, milky lotion, cream, eye cream, beauty serum, massage fee, pack fee, hand cream, body cream, cleansing fee, cleaning fee, sunscreen, etc.
  • Cosmetics, powder foundations, liquid foundations, and cosmetic base cosmetics can be exemplified, and examples of usage methods include a method of using hands or cotton, a method of applying to a nonwoven fabric, and the like.
  • the oil-in-water emulsion composition of the present invention can be used in various forms such as liquid, emulsion, cream, gel, foam, mist, solid, etc., depending on the combination with other components and the mechanism of the container.
  • the oil-in-water emulsified composition of the present invention and cosmetics containing the composition and / or external preparations for skin are sprayed in the form of a mist to be applied thinly and uniformly to the skin and hair.
  • the cosmetic of the present invention is contained in a container that can be sprayed in a mist form, such as an atomizer container, a trigger mist container, or an aerosol spray can.
  • oil-in-water emulsion composition of the present invention is mixed with various propellants in a quantitative and qualitative range that does not impair the effects of the present invention, depending on the purpose, hair foam, spray foam, hair mist, hair spray, etc. Aerosol products.
  • propellant liquefied petroleum gas, nitrogen gas, carbon dioxide gas, dimethyl ether and the like can be used.
  • the oil-in-water emulsified composition of the present invention can be used for various applications as described above, and among them, it is preferably used for hair. Specifically, it can be implemented as hair products such as hair rinses, hair packs, hair treatments using in baths, hair conditioners, hair lotions, split coat agents, hair milk, hair creams, etc. using out baths. And from the point of the effect of a component (A) among hair, it is more preferable to use it for hairdressing.
  • the semi-solid content was washed several times with methanol and dried to obtain 107 g of a pale yellow resinous substance.
  • the emery type starting material used was EMARSOL873 made by Cognis.
  • the fatty acid composition of this raw material was 60 mol% branched saturated fatty acids and 40 mol% other fatty acids (including 10 mol% palmitic acid). (The same applies hereinafter)
  • the degree of substitution was 2.2, the branched saturated fatty acid was 60 mol%, the other fatty acid was 40 mol% (internal palmitic acid was 10 mol%), the viscosity was 0 mPa ⁇ s, and the tackiness was 161 g.
  • Dextrin isoarachidic acid / palmitic acid ester
  • Dextrin (51.28 g) having an average glucose polymerization degree of 150 was dispersed in a mixed solvent consisting of 150 g of dimethylformamide and 60 g of pyridine at 70 ° C., and a mixture of 132 g of isoarachidic acid chloride and 12 g of palmitic acid chloride was added dropwise over 30 minutes. After completion of the dropwise addition, the reaction temperature was 80 ° C. and the reaction was performed for 5 hours. After completion of the reaction, the reaction solution was dispersed in methanol, and the upper layer was removed.
  • the semi-solid content was washed several times with methanol and dried to obtain 145 g of a pale yellow resinous substance.
  • (Branch saturated fatty acid 90mol% at the time of preparation) The degree of substitution was 1.1, isoarachidic acid 85 mol%, palmitic acid 15 mol%, viscosity was 0 mPa ⁇ s, and tackiness was 45 g.
  • the semi-solid content was washed several times with methanol and dried to obtain 95 g of a pale yellow resinous substance. (Branch saturated fatty acid 55 mol% when charged) The degree of substitution was 1.6, 51 mol% isononanoic acid, 49 mol% stearic acid, the viscosity was 0 mPa ⁇ s, and the tackiness was 64 g.
  • the semi-solid content was washed several times with methanol and dried to obtain 95 g of a pale yellow resinous substance.
  • the degree of substitution was 2.3, 2-ethylhexanoic acid 95 mol%, behenic acid 5 mol%, the viscosity was 0 mPa ⁇ s, and the tackiness was 138 g.
  • the semi-solid content was washed several times with methanol and dried to obtain 96 g of a pale yellow resinous material.
  • the degree of substitution was 2.8, 79 mol% of isopalmitic acid, 21 mol% of acetic acid, the viscosity was 0 mPa ⁇ s, and the tackiness was 430 g.
  • the semi-solid content was washed several times with methanol and dried to obtain 88 g of a pale yellow resinous substance.
  • Example 1 Hair mist (for out bath) of products 1 to 17 of the present invention and comparative products 1 to 12 A lotion-like hair mist is prepared according to the formulations shown in Tables 1 to 3 and the following production method, and “stability with time”, “no stickiness”, and “smoothness after finishing” are evaluated according to the following evaluation methods and criteria. Evaluation was made and the results are shown in Tables 1 to 3.
  • the hair mists (for out bath) of the inventive products 1 to 17 were all excellent in “time stability”, “use feeling (no stickiness)”, and “smoothness after finishing”.
  • the product 1 of the present invention which is a combination of the dextrin isostearate and isopropyl myristate of the present invention, has a high score of “smoothness of the finish” while maintaining the “use feeling (no stickiness)”. It was.
  • different types of dextrin fatty acid esters are used as the component (A) as in the comparative product 1, stickiness is felt during use, and the smoothness after finishing is not excellent.
  • the component (B) having a high “use feeling (no stickiness)” score was obtained as long as it was within the scope of the above claims.
  • stickiness was felt during use or emulsification failure occurred immediately after production, and stable production could not be achieved.
  • an emulsifier is selected as the component (C), but when used within the range of the inventive products 10 to 13, it is excellent in “use feeling (no stickiness)”, but “stable with time”. Also excellent.
  • different types such as comparative products 9 to 11 cannot be manufactured stably.
  • invention products 15 to 17 in which hydrocarbon oil is added as component (D) in addition to the ester oil of component (B) of the present invention are “use feeling (no stickiness)”, “smooth finish” ”Was maintained, and“ time stability ”was excellent.
  • a highly polar oil such as component (B) is generally prone to Ostwald ripening and is not highly stable when emulsified due to creaming or the like. It is thought that it is possible to effectively suppress the phenomenon of destabilizing emulsification such as Ostwald ripening by combining such nonpolar oil agents.
  • the average particle size of the emulsified droplets is 500 nm or less, and the viscosity is low and the fluidity is high.
  • the mist is also filled when used in a non-aerosol type trigger type mist container. It is a liquid oil-in-water emulsion composition that can be sprayed uniformly.
  • Example 2 Hair lotion (component) (%) 1. Dipropylene glycol 1 2. Oleyl alcohol 0.1 3. Dicocoyldimethylammonium chloride 0.5 4). Dextrin fatty acid ester of Reference Production Example 2 0.1 5. Polyoxyethylene hydrogenated castor oil (20 EO) 0.1 6). N-lauroyl-L-glutamate di (2-octyldodecyl) 0.1 7). Cetyl ethylhexanoate 0.2 8). Ethanol 10 9. Hydroxyethyl cellulose 0.1 10. Purified water remaining amount 11. Methylparaben 0.1 12 Cationized cellulose 0.1 13 Citric acid 0.01 14 Silylated silk peptide * 3 0.1 15. Fragrance 0.1 * 3: Promois S-700SIG (manufactured by Seiwa Kasei Co., Ltd.)
  • the hair lotion of Example 18 obtained as described above was an oil-in-water emulsion composition excellent in “aging stability”, “no stickiness”, and “smoothness after finishing”. Even when the dextrin fatty acid ester of Reference Production Example 7 is used in place of the dextrin fatty acid ester of Reference Production Example 2, good products can be obtained in these items.
  • Example 3 Hair milk (component) (%) 1 Propylene glycol 0.5 2 Ethanol 5.0 3 Polyoxyethylene hydrogenated castor oil (40 EO) 0.5 4 cetostearyl alcohol 1.0 5 Glyceryl monostearate 0.5 6 Dextrin fatty acid ester of Reference Production Example 3 0.3 7 Liquid paraffin 1.0 8 Isopropyl myristate 3.0 9 Alkyltrimethylammonium chloride solution (80%) * 4 0.4 10 Phenoxyethanol 0.1 11 Methyl paraoxybenzoate 0.1 12 Stearyltrimethylammonium chloride (80%) * 5 0.2 13 Purified Water Remaining 14 LIPIDURE-PMB 0.02 15 (Bisbutyroxyamodimethicone / PEG-60) copolymer 0.2 16 Polyoxyethylene (10) methyl glucoside 2.0 17.
  • the hair cream of Example 3 which is a product of the present invention was an oil-in-water emulsion composition excellent in “time stability”, “no stickiness” and “smoothness after finishing”.
  • Example 4 Hair spray (component solution) (%) 1 Polyoxyethylene hydrogenated castor oil (10E.O.) 2.5 2 Dextrin fatty acid ester of Reference Production Example 4 0.1 3 Amodimethicone 1.0 4 Isononyl isononanoate 0.5 5 Fragrance 0.5 6 Kerosene 0.5 7 Ethylhexyl methoxycinnamate 0.1 8 N-lauroyl-L-glutamate di (phytosteryl Behenyl 2-octyldodecyl) 0.1 9 Argania spinosa kernel oil 0.1 10 L-serine 0.5 11 1,3-butylene glycol 0.5 12 Ethanol remaining
  • the hair spray of Example 4 which is a product of the present invention, was an oil-in-water emulsified composition excellent in “aging stability”, “no stickiness”, and “smoothness after finishing”. Even if the dextrin fatty acid ester of Reference Production Example 9 is used in place of the dextrin fatty acid ester of Reference Production Example 4, good products can be obtained in these items.
  • Example 5 Daytime serum (component) (%) 1 Polyoxyethylene hydrogenated castor oil (20 EO) 0.1 2 1,3-butylene glycol 12.0 3 Methylparaben 0.1 4 Purified water 4.3 5 Acrylic acid / acryloyldimethyltaurine sodium copolymer * 8 1.5 6 Purified water remaining 7 Ethanol 10.0 8 Dextrin fatty acid ester of Reference Production Example 5 0.1 9 Isotridecyl isononanoate 1.0 10 Ethylhexyl methoxycinnamate 7.5 11 Dimethicone 2.5 12 Cyclomethicone 1.0 13 Astaxanthin * 9 0.01 * 8: SIMULGEL EG (made by SEPPIC) * 9: Astaxanthin 5-C (Oryza Oil Chemical Co., Ltd.)
  • the daytime cosmetic liquid of Example 5 which is a product of the present invention was an oil-in-water emulsion composition excellent in “time stability”, “no stickiness”, and “smoothness after finishing”.

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WO2020027076A1 (ja) * 2018-07-30 2020-02-06 株式会社 資生堂 水中油型乳化化粧料
JP2020029436A (ja) * 2018-08-24 2020-02-27 株式会社ダリヤ 整髪料組成物
WO2023223838A1 (ja) * 2022-05-18 2023-11-23 株式会社 資生堂 上地化粧料

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US20230414481A1 (en) * 2020-11-02 2023-12-28 Asahi Kasei Finechem Co., Ltd. Composition and Method for Producing Same and Cosmetic Agent

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JP2013071919A (ja) * 2011-09-28 2013-04-22 Kose Corp 皮膚柔軟化用皮膚外用剤
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WO2020027076A1 (ja) * 2018-07-30 2020-02-06 株式会社 資生堂 水中油型乳化化粧料
JPWO2020027076A1 (ja) * 2018-07-30 2021-08-02 株式会社 資生堂 水中油型乳化化粧料
JP2020029436A (ja) * 2018-08-24 2020-02-27 株式会社ダリヤ 整髪料組成物
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WO2023223838A1 (ja) * 2022-05-18 2023-11-23 株式会社 資生堂 上地化粧料

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