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WO2018199594A1 - Composition en émulsion de type huile dans eau contenant des agrégats de particules en émulsion et son procédé de préparation - Google Patents

Composition en émulsion de type huile dans eau contenant des agrégats de particules en émulsion et son procédé de préparation Download PDF

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Publication number
WO2018199594A1
WO2018199594A1 PCT/KR2018/004744 KR2018004744W WO2018199594A1 WO 2018199594 A1 WO2018199594 A1 WO 2018199594A1 KR 2018004744 W KR2018004744 W KR 2018004744W WO 2018199594 A1 WO2018199594 A1 WO 2018199594A1
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Prior art keywords
hydrophilic
polymer
group
acrylate
composition
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English (en)
Korean (ko)
Inventor
김영선
남진
안순애
피봉수
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Amorepacific Corp
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Amorepacific Corp
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Priority claimed from KR1020180046741A external-priority patent/KR102088804B1/ko
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    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present specification describes an oil-in-water emulsion composition including an emulsion particle cluster and a method of manufacturing the same.
  • the stability over time is relatively excellent, but oily (oily) in the feeling of use, it is difficult to give a fresh feeling.
  • the size of the emulsified particles is large, the water burst effect can be imparted to the feeling of use, but the stability of the emulsified particles is lowered.
  • the problem to be solved by the present invention is to provide an emulsion composition having a fine size and excellent stability of the emulsion particles.
  • the problem to be solved by the present invention is to provide an emulsified composition having a fine size of the emulsified particles, but excellent in the water bursting effect, a fresh feeling.
  • the problem to be solved by the present invention is to provide an emulsion composition showing excellent stability over a wide temperature range.
  • the problem to be solved by the present invention is to provide a stable emulsion composition without using an excessive amount of thickener.
  • the present invention provides a branched chain polymer or carbomer having a lipophilic alkyl chain; Into an oil-in-water (O / W) emulsion composition comprising; and a double spheroid type polymer amphiphilic anisotropic powder consisting of a hydrophilic one and a hydrophobic other.
  • O / W oil-in-water
  • the powder has a structure in which the hydrophobic other partially penetrates into the inside of the hydrophilic one to form a hydrophilic one core, and the shell of the hydrophilic one includes a functional group, and provides an oil-in-water emulsion cosmetic composition.
  • the present invention is a method for preparing an oil-in-water (O / W) emulsion composition comprising an emulsion particle cluster (cluster),
  • the powder has a structure in which the hydrophobic other partially penetrates into the inside of the hydrophilic one to form a hydrophilic one core, and the shell of the hydrophilic one includes a functional group.
  • the present invention can provide an emulsion composition having a fine size of the emulsion particles and excellent stability.
  • the present invention can provide an emulsified composition having a fine size of the emulsified particles but having an excellent water burst effect and a neat feeling of use.
  • the present invention may provide an emulsion composition that exhibits good stability over a wide temperature range.
  • the present invention can provide a stable emulsion composition without the use of thickeners in excess.
  • FIG. 1 is a schematic diagram schematically showing a method for preparing a composition according to an embodiment of the present invention.
  • FIG. 2 is a schematic diagram of forming an amphipathic anisotropic powder.
  • Example 3 is an optical micrograph immediately after the preparation of the emulsified particles of Example 1 and Comparative Examples 1-3 and after 10 weeks storage at 45 ° C.
  • Example 4 is a graph showing changes in viscosity over time in Example 1 and Comparative Examples 1-3.
  • the particle size of the amphipathic anisotropic powder herein is a measure of the maximum length, which is the longest length of the powder particles.
  • the particle size range of the amphipathic anisotropic powder herein means that at least 95% of the amphipathic anisotropic powder present in the composition falls within this range.
  • an oil-in-water type (O / W) emulsion composition including a branched chain polymer or carbomer having a lipophilic alkyl chain as a side, and an amphiphilic anisotropic powder may be provided.
  • the branched chain polymer or carbomer having the lipophilic alkyl chain as a side may be adsorbed onto the emulsified particles to form an emulsified particle-polymer complex due to hydrophobic interaction with the amphiphilic anisotropic powder.
  • These emulsified particle-polymer composites can network with each other to form an emulsified particle matrix.
  • the branched chain polymer having the lipophilic alkyl chain as an acrylate / C 10-30 alkyl acrylate crosspolymer (Acrylate / C 10-30 Alkyl Acrylate Crosspolymer), acrylate / C 12-22 alkyl methacrylate copolymer (Acrylate / C12-22 Alkyl Metacrylate Copolymer), Acrylates / Beheneth-25 Methacrylate Copolymer or Acrylate / Ceteth-20 Metacrylate Copolymer ) Can be used.
  • the composition may include a branched chain polymer or carbomer with the lipophilic alkyl chain as an amount of 0.01 wt% to 1 wt%, for example 0.02 wt% to 0.08 wt%, based on the total weight of the composition.
  • the composition may further comprise a polar organic solvent.
  • the branched chain polymer or carbomer having the lipophilic alkyl chain as a side reacts with the polar organic solvent to exhibit shrinking of the branched chain polymer or carbomer.
  • the polar organic solvent is added to the emulsion particle matrix, the branched chain polymer or carbomer included in the emulsion particle matrix shrinks, and the emulsion particle-polymer complexes are entangled together in a group.
  • the emulsion particle-polymer composites are densely clustered to form emulsified particle clusters.
  • the polar organic solvent may be ethanol, acetic acid, dimethylamide, methanol, pyridine, ethylene glycol, acetone and the like, but is not limited thereto. In one embodiment, the polar organic solvent may be ethanol.
  • the composition may comprise 5% to 40% by weight, for example 10% to 30% by weight, of the polar organic solvent relative to the total weight of the composition.
  • the emulsified particle cluster maintains the ionicity of the particles, the emulsified particle cluster can be stably maintained without the phenomenon of fusion between the emulsified particles in the formed emulsified particle cluster due to the repulsive force between charges.
  • the average particle size of the emulsified particle cluster may be 1 to 500 ⁇ m, for example 30 to 300 ⁇ m.
  • the average particle size of the emulsified particle clusters refers to the average diameter of the major axis and minor axis, and means that at least 95% of the clusters present in the composition fall within this range.
  • the composition may further comprise a primary thickener.
  • the primary thickener increases the dosage form, and may serve as a secondary surfactant to refine the size of the emulsified particles formed by the anisotropic powder.
  • the emulsified particles formed before adding the primary thickener may be large emulsified particles having an average particle diameter of 1 to 100 ⁇ m.
  • the average particle diameter of the said large emulsion particle means the average value of the diameter of a single particle. In the state of the said large emulsion particle
  • the average particle diameter of the macroemulsion particles may be, for example, 5 to 100 ⁇ m, 10 to 100 ⁇ m, 10 to 50 ⁇ m, or 25 ⁇ m.
  • the average particle diameter of the emulsified particles is at least 1 ⁇ m, at least 2 ⁇ m, at least 3 ⁇ m, at least 4 ⁇ m, at least 5 ⁇ m, at least 6 ⁇ m, at least 7 ⁇ m, at least 8 ⁇ m, at least 9 ⁇ m, at least 10 ⁇ m, 15 ⁇ m or more, 20 ⁇ m or more, 25 ⁇ m or more, 30 ⁇ m or more, 40 ⁇ m or more, 50 ⁇ m or more, or 80 ⁇ m or more, 100 ⁇ m or less, 90 ⁇ m or less, 80 ⁇ m or less, 70 ⁇ m or less, 60 ⁇ m or less, 50 ⁇ m, 40 ⁇ m, 30 ⁇ m, 25 ⁇ m, 20 ⁇ m, 15 ⁇ m, 10 ⁇ m or 5 ⁇ m or less.
  • the hydrophobic portion and the hydrophilic portion of the amphiphilic anisotropic powder can form large emulsion particles by having different orientations to the interface. While the interfacial film formed by the general molecular level surfactant forms a dynamic emulsification state, the emulsified particles formed by the amphipathic anisotropic powder increase the thickness of the interfacial film to several hundred nm and form a strong interfacial film through strong bonding between the powders. Done. Emulsification stability can be improved by forming such an interface film.
  • the emulsified particles to be refined by the addition of the primary thickener may be fine emulsified particles having an average particle diameter of 1 ⁇ m to 20 ⁇ m.
  • the average particle diameter of the fine emulsified particles means an average value of the diameters of the single particles.
  • the average particle diameter range of the fine emulsified particles means that 95% or more, for example, 99% or more of the emulsified particles present in the composition fall within the range, and the particle size may be uniform.
  • the average particle diameter of the fine emulsified particles is at least 1 ⁇ m, at least 2 ⁇ m, at least 3 ⁇ m, at least 4 ⁇ m, at least 5 ⁇ m, at least 6 ⁇ m, at least 7 ⁇ m, at least 8 ⁇ m, at least 9 ⁇ m, at least 10 ⁇ m.
  • the primary thickener may be used without limitation as long as it is commonly used in the art as a thickener, but branched polymers and carbomers having side chains of the lipophilic alkyl chain included in the emulsion cluster are excluded.
  • the primary thickener may be polyacrylate-13, polyisobutene, polysorbate 30, or the like.
  • the composition may comprise from 0.01% to 3% by weight, for example from 0.05% to 2% by weight, based on the total weight of the composition.
  • composition according to the present embodiment has a viscosity of at least 1000 cps, at least 1100 cps, at least 1200 cps, at least 1300 cps, at least 1400 cps, at least 1500 cps, at least 1600 cps, at least 1700 cps, and at least 1800 cps.
  • amphiphilic anisotropic powder may be a double spheroid type polymer amphipathic anisotropic powder composed of hydrophilic one and hydrophobic other.
  • the powder has a structure in which the hydrophobic other partially penetrates into the inside of the hydrophilic one to form a hydrophilic one core, and the hydrophilic one may include a functional group.
  • the powder may be a double spheroid type, that is, a three-dimensional nephroid shape having a shape in which two spheroids are combined, and a symmetrical shape and an asymmetrical snowman based on the combined part. snowman) shape or asymmetrical inverse snowman shape.
  • the snowman shape means that the first and second polymer spheroids having different sizes are bonded to each other.
  • the spheroid may be, for example, a sphere, globoid or oval shape, and may have a long axis length of micro units or nano units based on the longest length in the body cross section. have.
  • the hydrophilic one side may have a core-shell structure in which the core is made of the same polymer as the hydrophobic other side, and the hydrophilic one side and the hydrophobic other side may form one spheroid shape each of the double spheroids.
  • the coupling portion between the two spheroids of the double spheroid can be made into a structure that is continuous from the hydrophilic one core to the hydrophobic other.
  • the hydrophilic one core and the hydrophobic other include a vinyl polymer
  • the hydrophilic one shell may include a copolymer of a vinyl monomer and a monomer containing a functional group.
  • the vinyl polymer may be a vinyl aromatic polymer, for example, may be polystyrene.
  • the vinyl monomer may be vinyl aromatic. In one example, the vinyl monomer may be substituted or unsubstituted styrene.
  • the functional group may be a siloxane.
  • the monomer containing a functional group may be a siloxane-containing (meth) acrylate, specifically, 3- (trimethoxysilyl) propyl acrylate, 3- (trimethoxysilyl) propyl methacrylate, vinyl Triethoxysilane, vinyltrimethoxysilane or mixtures thereof.
  • the shell of the hydrophilic one side may be further introduced with a hydrophilic functional group.
  • the hydrophilic functional group may be a negatively charged or positively charged functional group or polyethylene glycol (PEG) series, carboxylic acid group, sulfone group, phosphate group, amino group, alkoxy group, ester group, acetate group, polyethylene glycol group and hydride It may be at least one selected from the group consisting of a hydroxyl group.
  • PEG polyethylene glycol
  • the hydrophilic one shell may be further introduced with a functional group containing a sugar.
  • the sugar-containing functional group is N- ⁇ N- (3-triethoxysilylpropyl) aminoethyl ⁇ gluconamide, N- (3-triethoxysilylpropyl) gluconamide and N- ⁇ N It may be derived from one or more selected from the group consisting of-(3-triethoxysilylpropyl) aminoethyl ⁇ -oligo-hyaluronamide.
  • the amphipathic anisotropic powder may have a particle size of 100 to 1500 nm.
  • the amphipathic anisotropic powder may have a particle size of 100 to 500 nm, or 200 to 300 nm.
  • the amphiphilic anisotropic powder has a particle size of 100 nm or more, 200 nm or more, 300 nm or more, 400 nm or more, 500 nm or more, 600 nm or more, 700 nm or more, 800 nm or more, 900 nm or more, 1000 nm 1100 nm or more, 1200 nm or more, 1300 nm or more, or 1400 nm or more, 1500 nm or less, 1400 nm or less, 1300 nm or less, 1200 nm or less, 1100 nm or less, 1000 nm or less, 900 nm or less, 800 nm or less , 700 nm or less, 600 n
  • the composition comprises the amphiphilic anisotropic powder, for example, based on the total weight of the composition, for example, 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight or more , At least 0.7 wt%, at least 0.8 wt%, at least 0.9 wt%, or at least 1.0 wt%, at most 20 wt%, at most 19 wt%, at most 18 wt%, at most 17 wt%, at most 16 wt%, 15 wt% Or less, 14 or less, 13 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less Or less than 4%, or less than or equal to 3% by weight.
  • the composition may include the amphiphilic anisotropic powder in an amount of 0.1% to 20% by weight, for example, 1% to 3%, based on the total weight of the composition.
  • Stable emulsion particles can be formed within the above range, and emulsion particles of appropriate size can be formed.
  • the amphipathic anisotropic powder comprises one hydrophilic one (first polymer spheroid) and the other hydrophobic (second polymer spheroid), the hydrophilic one has a core-shell structure, the other hydrophilic one is the hydrophilic one It is a structure which penetrates at least partially into the inside and forms one core of hydrophilicity, and the said hydrophilic one shell may contain a functional group.
  • the amphipathic anisotropic powder is prepared by polymerizing a first monomer to prepare a core of a first polymer spheroid, and coating a core of the first polymer spheroid to the first polymer sp of the core-shell structure It may be prepared to prepare the Lloyd, and reacting the first polymer spheroid and the first monomer of the core-shell structure to prepare an amphiphilic anisotropic powder in which the second polymer spheroid is formed.
  • Figure 2 is a schematic diagram showing the principle of formation of amphipathic anisotropic powder according to an embodiment of the present invention.
  • the core of the first polymer spheroid may be penetrated through the shell of the first polymer spheroid, and then powdered to form a second polymer spheroid.
  • the amphiphilic anisotropic powder may be prepared by (1) stirring a first monomer and a polymerization initiator to prepare a core of a first polymer spheroid; (2) stirring the core of the prepared first polymer spheroid with a monomer containing a first monomer, a polymerization initiator, and a functional group to prepare a coated core-shell structured first polymer spheroid; (3) stirring the first polymer spheroid of the core-shell structure prepared above with the second monomer and the polymerization initiator to prepare an amphiphilic anisotropic powder in which the second polymer spheroid is formed.
  • the stirring may be rotary stirring.
  • Rotational agitation is preferred because uniform mechanical mixing is required along with chemical modification to produce uniform particles.
  • the rotary stirring may be rotary stirring in a cylindrical rotary reactor, but the rotary stirring method is not limited thereto.
  • the size and location of the baffles in the cylindrical rotary reactor and the degree of spacing with the impeller greatly affect the uniformity of the particles produced. It is desirable to minimize the blade gap between the inner wing and the impeller to equalize the convective flow and its strength, and to supply the powder reaction liquid below the wing length and maintain the impeller rotation speed at a high speed. It may be rotated at a highway of 200 rpm or more, and the ratio of the length of the diameter and the height of the reactor may be 1 to 3: 1 to 5, more specifically, 10 to 30 cm in diameter and 10 to 50 cm in height. The reactor size can vary in proportion to the reaction capacity. In addition, the material of the cylindrical rotary reactor may be a ceramic, glass, and the like, the temperature of the stirring is preferably 50 to 90 °C.
  • the simple rotary method enables the production of uniform particles and is a low energy method that requires less energy, and has a characteristic of enabling mass production by maximizing reaction efficiency.
  • the tumbling method in which the reactor itself rotates in the related art requires high energy and rotates the reactor at a predetermined angle, thus requiring high energy and restricting the size of the reactor. Due to the limitations of the reactor size, the amount produced is also limited to small amounts of about several hundred mg to several g, making it unsuitable for mass production.
  • the first monomer and the second monomer may be the same or different, specifically, may be a vinyl monomer.
  • the first monomer added in step (2) is the same as the first monomer used in step (1), the polymerization initiator used in each step may be the same or different.
  • the vinyl monomer may be vinyl aromatic. In one example, the vinyl monomer may be substituted or unsubstituted styrene.
  • the polymerization initiator may be a radical polymerization initiator, specifically, may be a peroxide-based, azo-based or a mixture thereof. Moreover, ammonium persulfate, sodium persulfate, potassium persulfate can also be used.
  • the first monomer and the polymerization initiator may be mixed in a weight ratio of 100 to 1000: 1. In another aspect, the first monomer and the polymerization initiator may be mixed in a weight ratio of 100 to 750: 1, or 100 to 500: 1, or 100 to 250: 1.
  • a stabilizer may be added together with the first monomer and the polymerization initiator to mix the first monomer, the polymerization initiator, and the stabilizer in a weight ratio of 100 to 1000: 1: 0.001 to 5.
  • the powder size and shape are determined according to the size adjustment of the first polymer spheroid in the initial stage (1), and the first polymer spheroid size can be adjusted according to the weight ratio of the first monomer, the polymerization initiator and the stabilizer.
  • the weight ratio of the said range there exists an effect which can raise the uniformity of anisotropic powder.
  • By mixing in the weight ratio in the above range it is possible to significantly increase the uniformity of the shape and size of the anisotropic powder.
  • the stabilizer may be an ionic vinyl monomer, specifically sodium 4-vinylbenzenesulfonate may be used. Stabilizers prevent swelling of the resulting particles and impart positive or negative charges to the surface of the powder to electrostatically prevent mutual coalescence (bonding) during particle generation.
  • the weight ratio of the first monomer, the polymerization initiator and the stabilizer is 80 to 135: 1: 1 to 5, specifically 95 to 120: 1: 1 to 2-4 It can be prepared from 1 polymer spheroid.
  • the weight ratio of the first monomer, the polymerization initiator and the stabilizer is 225 to 240: 1: 1 to 3, specifically 230 to 235: 1: 1 to 3 It can be prepared from the first polymeric spheroid.
  • the amphiphilic anisotropic powder has a size of 1100 to 2500 nm
  • the first polymer having a weight ratio of the first monomer, the polymerization initiator, and the stabilizer is 110 to 130: 1: 0, specifically 115 to 125: 1: 0 It can be prepared from spheroids.
  • amphipathic anisotropic powder of the asymmetrical snowman shape has a weight ratio of the first monomer, the polymerization initiator, and the stabilizer of 100 to 140: 1: 8 to 12, specifically 110 to 130: 1: 9 to 11 It can be prepared from polymeric spheroids.
  • amphipathic anisotropic powder of the asymmetric inverse snowman shape is made of a weight ratio of the first monomer, the polymerization initiator, and the stabilizing agent is 100 to 140: 1: 1 to 5, specifically 110 to 130: 1: 1 to 2-4 It can be prepared from 1 polymer spheroid.
  • the monomer containing a functional group in the step (2) may be a siloxane-containing (meth) acrylate, specifically, 3- (trimethoxysilyl) propyl acrylate, 3- (trimethoxysilyl) propyl Methacrylate, vinyltriethoxysilane, vinyltrimethoxysilane or mixtures thereof.
  • the monomer containing the first monomer, the polymerization initiator and the functional group in the step (2) may be mixed in a weight ratio of 30 to 100: 0.2 to 1.0: 1 to 20.
  • the first monomer, the polymerization initiator and the monomer containing a functional group may be mixed in a weight ratio of 150 to 300: 1: 6 to 40.
  • the degree of coating can be adjusted according to the weight ratio, and the shape of the amphipathic anisotropic powder is subsequently determined according to the degree of coating, and when reacting with the weight ratio, the coating thickness increases to about 10-30%, specifically 20%, relative to the initial thickness.
  • the coating is too thick so that powdering does not proceed or is too thin so that the powdering proceeds well without the problem of powdering in multiple directions. Moreover, by mixing in the weight ratio of the said range, there exists an effect which can raise the uniformity of anisotropic powder.
  • a part of the core of the first polymer spheroid protrudes through the shell from one direction of the first polymer spheroid of the core-shell structure, and the protrusion grows by the polymer of the second monomer to form an anisotropic powder. It can form the form of.
  • the second monomer and the polymerization initiator may be mixed in a weight ratio of 150 to 250: 1.
  • the second monomer and the polymerization initiator are 160 to 250: 1, or 170 to 250: 1, or 180 to 250: 1, or 190 to 250: 1, or 200 to 250: 1, or 210 to 250 It can be mixed in a weight ratio of: 1, or 220 to 250: 1, or 230 to 250: 1, or 240 to 250: 1.
  • the second monomer, the polymerization initiator and the stabilizer may be added together with the second monomer and the polymerization initiator to mix the second monomer, the polymerization initiator and the stabilizer in a weight ratio of 150 to 250: 1: 1: 0.001 to 5.
  • the specific kind of stabilizer is as above-mentioned.
  • the second monomer content in the step (3) may be mixed to 40 to 300 parts by weight when the weight of the first polymer spheroid of the core-shell structure is 100 parts by weight.
  • an asymmetric snowman type powder is obtained, and 100 to 150 parts by weight, or 110 to 150 parts by weight.
  • parts by weight a symmetrical powder is obtained, and in the case of 150 to 300 parts by weight, or in the case of 160 to 300 parts by weight, an asymmetric inverse snowman type powder is obtained.
  • by mixing in the weight ratio of the said range there exists an effect which can raise the uniformity of anisotropic powder.
  • (4) when preparing the amphipathic anisotropic powder according to an embodiment of the present invention, after the step (3), (4) may further include introducing a hydrophilic functional group into the prepared anisotropic powder. have.
  • the hydrophilic functional group in step (4) is not limited thereto, but may be introduced using a silane coupling agent and a reaction regulator.
  • the silane coupling agent is (3-aminopropyl) trimethoxysilane, N- [3- (trimethoxysilyl) propyl] ethylenediamine, N- [3- (trimethoxysilyl) propyl] ethylenedi Ammonium chloride, (N-succinyl-3-aminopropyl) trimethoxysilane, 1- [3- (trimethoxysilyl) propyl] urea and 3-[(trimethoxysilyl) propyloxy] -1,2 It may be one or more selected from the group consisting of propanediol, specifically N- [3- (trimethoxysilyl) propyl] ethylenediamine.
  • the silane coupling agent may be mixed in an amount of 35 to 65 parts by weight, for example 40 to 60 parts by weight, based on 100 parts by weight of the anisotropic powder prepared in step (3). Hydrophilization can be suitably made within the said range.
  • reaction modifier may be ammonium hydroxide.
  • reaction regulator may be mixed in an amount of 85 parts by weight to 115 parts by weight, for example 90 parts by weight to 110 parts by weight, based on 100 parts by weight of the anisotropic powder prepared in step (3). Hydrophilization can be suitably made within the said range.
  • the functional group containing sugar in step (4) is not limited thereto, but may be introduced using a sugar-containing silane coupling agent and a reaction regulator.
  • the sugar-containing silane coupling agent is N- ⁇ N- (3-triethoxysilylpropyl) aminoethyl ⁇ gluconamide, N- (3-triethoxysilylpropyl) gluconamide And N- ⁇ N- (3-triethoxysilylpropyl) aminoethyl ⁇ -oligo-hyaluronamide.
  • the reaction modifier may be ammonium hydroxide.
  • the reaction regulator may be mixed in an amount of 85 parts by weight to 115 parts by weight, for example 90 parts by weight to 110 parts by weight, based on 100 parts by weight of the anisotropic powder prepared in step (3).
  • Introduction of the functional group containing a sugar in the said range can be made suitably.
  • Amphiphilic anisotropic powder according to the above method does not use a crosslinking agent, there is no entanglement in production, the yield is high and uniform, and it is easy to mass-produce compared to the tumbling method using a simple stirring method.
  • an oil-in-water (O / W) emulsion composition including an emulsified particle cluster.
  • FIG. 1 is a schematic diagram schematically showing a method for preparing a composition according to an embodiment of the present invention.
  • the production method comprises the addition of a double spheroid type polymer amphiphilic anisotropic powder to the aqueous phase to form large emulsion particles; A primary thickener is added to form fine emulsified particles, and a branched chain polymer or carbomer having a lipophilic alkyl chain as a side, and a polar organic solvent are added to add a lipophilic alkyl chain to the fine emulsified particles.
  • Emulsified particle-polymer complexes adsorbed by branched chain polymers or carbomers having side chains can form clusters of emulsified particles that are densely clustered.
  • polymer refers to a branched chain polymer or carbomer with a lipophilic alkyl chain.
  • an emulsified particle cluster as in the embodiments of the present invention It does not form, it will contain a simple dispersed emulsion particles.
  • amphipathic anisotropic powder is omitted as it is described in the above-described composition according to an embodiment of the present invention.
  • a branched chain polymer or carbomer is added to the fine emulsified particles, and the branched polymer or carbomer adsorbed to the microemulsified particles is adsorbed.
  • the emulsion particle-polymer complexes form a network of emulsion particle matrix in which a network is formed, and a polar organic solvent is added thereto so that the branched polymer or carbomer having a lipophilic alkyl chain included in the matrix shrinks, thereby emulsifying the emulsion.
  • Particle-polymer complexes may be densely clustered to form emulsified particle clusters.
  • the composition according to the present embodiment has a very high stability because the emulsion particles exist in the form of emulsion particle clusters, it is possible to provide a stable emulsion composition without using an excessive amount of a thickener. Furthermore, since a large number of emulsified particles exist in a clustered state, the size of the emulsified particles is fine, but the water burst effect generated when the emulsified particle interface collapses due to friction during use can provide a fresh feeling.
  • composition according to the present embodiment may exhibit emulsion stability over time in a wide temperature range, and the temperature may be, for example, -15 ° C to 60 ° C.
  • the composition according to the embodiments of the present invention may be a cosmetic composition.
  • the cosmetic composition may be formulated containing a cosmetically or dermatologically acceptable medium or base. It is any formulation suitable for topical application, in the form of suspensions, microemulsions, microcapsules, microgranules or ionic (liposomal) and nonionic vesicle dispersants or creams, skins, lotions, powders, ointments, sprays or concealers. It may be provided in the form of a stick. It may also be used in the form of a foam or in the form of an aerosol composition further containing a compressed propellant. These compositions can be prepared according to conventional methods in the art.
  • the cosmetic composition according to the embodiments of the present invention may be a powder, a fatty substance, an organic solvent, a dissolving agent, a thickening agent, a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, a surfactant.
  • ionic or nonionic emulsifiers fillers, metal ion sequestrants, chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or cosmetics It may contain adjuvants conventionally used in the cosmetic or dermatological fields, such as any other ingredients used. Such adjuvants are introduced in amounts generally used in the cosmetic or dermatological arts.
  • the cosmetic composition according to the embodiments of the present invention may further contain a skin absorption promoting substance to increase the skin improving effect.
  • the component used by the following preparation example is as follows.
  • SVBS Sodium vinyl benzene sulfonate (stabilizer)
  • AIBN Azobisisobutyronitrile (polymerization initiator)
  • polystyrene-coreshell (PS-CS) aqueous dispersion solution obtained as a result of the reaction 40 g of styrene as a monomer, 0.35 g of sodium 4-vinylbenzenesulfonate as a stabilizer, and azo as a polymerization initiator 0.2 g of bisisobutyronitrile (Azobisisobutyronitrile, AIBN) was mixed and heated to 75 ° C. for 8 hours. The reaction was stirred in a cylindrical rotary reactor to produce an amphipathic anisotropic powder with an average particle size of 235 ⁇ m.
  • PS-CS polystyrene-coreshell
  • Example 1 To prepare an oil-in-water emulsion composition of Example 1 and Comparative Example 1 according to the composition of Table 2.
  • Example 1 In order to compare the emulsified particles, the emulsified particles prepared in Example 1 and Comparative Examples 1-3 were stored immediately after the preparation and at 45 ° C. for 10 weeks, and then observed with an optical microscope. An optical micrograph is shown in FIG. The size of the particles is shown in Table 3.
  • Example 1 emulsified particles formed in fine sizes dense together to form clusters, and no further aggregation or fusion was observed between the emulsified particle clusters. This is considered to be because the anionicity of the emulsified particles is maintained so that a repulsion force exists between the clusters.
  • Comparative Example 1 without a branched chain polymer or carbomer with a lipophilic alkyl chain the size of the emulsified particles is similar to Example 1, but the same cluster as in Example 1 is dispersed without forming You can see that it exists in a state. In the case of Comparative Example 2 using a different polymer from the present invention, no emulsion particle clusters are formed, and the emulsion particles of a small size are present in a dispersed state.
  • Example 1 In the case of the composition of Example 1, it can be confirmed that even after being kept at a high temperature for a long time, it is stably maintained without fusion of emulsified particles and without further aggregation of emulsified particle clusters. In Comparative Examples 1 and 2, cluster particles cannot be formed even after elapse of time. In the case of Comparative Example 3, the initial particle size was small and the pattern of the particles was different by emulsification with the surfactant, and after 10 weeks, it was confirmed that the aggregation phenomenon was caused by the instability of the formulation.
  • Example 1 The compositions prepared in Example 1 and Comparative Examples 1 to 3 were measured for 4 weeks at 30 ° C. using a viscosity meter (BROOKFIELD Viscometer, SPINDLE # 4, 12 RPM, 2MIN.) And the measured viscosity is shown in FIG. 4.
  • BROOKFIELD Viscometer SPINDLE # 4, 12 RPM, 2MIN.
  • Example 1 shows uniform stability even after 4 weeks.
  • Comparative Example 2 used a different type of polymer has a lower viscosity than the example.
  • Comparative Example 3 using a different surfactant it can be confirmed that the viscosity drop phenomenon does not maintain stability.
  • Example 1 The composition prepared in Example 1 and Comparative Examples 1 to 3 was used to 20 women aged 25 to 40 years to evaluate the feeling of use. With regard to the items of freshness, bursting water and oiliness (please describe the feeling factor that is excellent due to the cluster particles), the results were evaluated on a five-point scale (1 point: very poor to 5 points: very good). It is shown in Table 4 below.
  • Example 1 in Example 1 forming the emulsified particle cluster, although the size of the emulsified particle itself is fine, when used by the emulsified particle cluster formation, the freshness, water bursting effect is excellent, and it shows excellent feeling of not feeling oily. In the case of the compositions of Comparative Examples 1 to 3, which do not form clusters, it can be seen that the results exhibit an oily feeling.

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Abstract

La présente invention concerne une composition cosmétique en émulsion de type huile dans eau, la composition de type huile dans eau contenant : un polymère à chaîne ramifiée comportant une chaîne alkyle lipophile en tant que ramification latérale ou un carbomère ; et une poudre anisotrope amphiphile polymère de type double sphéroïde dont l'une des faces est hydrophile et l'autre hydrophobe, la poudre présentant une structure dans laquelle l'autre face hydrophobe s'infiltre partiellement dans la face hydrophile pour former le noyau de la face hydrophile, et l'enveloppe de la face hydrophile comprend un groupe fonctionnel.
PCT/KR2018/004744 2017-04-25 2018-04-24 Composition en émulsion de type huile dans eau contenant des agrégats de particules en émulsion et son procédé de préparation Ceased WO2018199594A1 (fr)

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KR1020180046741A KR102088804B1 (ko) 2017-04-25 2018-04-23 유화 입자 클러스터를 포함하는 수중유형 유화 조성물 및 그 제조방법

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5688831A (en) * 1993-06-11 1997-11-18 The Procter & Gamble Company Cosmetic make-up compositions
KR100716802B1 (ko) * 2005-12-30 2007-05-14 (주)아모레퍼시픽 산성도 민감성 고분자를 포함한 고분자-리포좀 나노복합체제조 및 이를 함유하는 피부 외용제 조성물
JP2010285610A (ja) * 2009-05-11 2010-12-24 Kose Corp 親疎水異方性板状粒子及びその製造方法、並びにそれからなる乳化剤
KR20150138012A (ko) * 2014-05-30 2015-12-09 (주)아모레퍼시픽 양친매성 이방성 분체를 포함하는 화장료 조성물 및 이의 제조방법
KR20160081820A (ko) * 2014-12-31 2016-07-08 (주)아모레퍼시픽 다양한 유화 입자 사이즈를 함유하는 혼성 유화 조성물 및 그 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5688831A (en) * 1993-06-11 1997-11-18 The Procter & Gamble Company Cosmetic make-up compositions
KR100716802B1 (ko) * 2005-12-30 2007-05-14 (주)아모레퍼시픽 산성도 민감성 고분자를 포함한 고분자-리포좀 나노복합체제조 및 이를 함유하는 피부 외용제 조성물
JP2010285610A (ja) * 2009-05-11 2010-12-24 Kose Corp 親疎水異方性板状粒子及びその製造方法、並びにそれからなる乳化剤
KR20150138012A (ko) * 2014-05-30 2015-12-09 (주)아모레퍼시픽 양친매성 이방성 분체를 포함하는 화장료 조성물 및 이의 제조방법
KR20160081820A (ko) * 2014-12-31 2016-07-08 (주)아모레퍼시픽 다양한 유화 입자 사이즈를 함유하는 혼성 유화 조성물 및 그 제조방법

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