WO2019108008A1 - Composition d'émulsion comprenant une poudre anisotrope amphiphile et présentant une stabilité améliorée - Google Patents

Composition d'émulsion comprenant une poudre anisotrope amphiphile et présentant une stabilité améliorée Download PDF

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WO2019108008A1
WO2019108008A1 PCT/KR2018/015069 KR2018015069W WO2019108008A1 WO 2019108008 A1 WO2019108008 A1 WO 2019108008A1 KR 2018015069 W KR2018015069 W KR 2018015069W WO 2019108008 A1 WO2019108008 A1 WO 2019108008A1
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신지식
김선영
남진
박승한
서병휘
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(주)아모레퍼시픽
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Priority claimed from KR1020180151000A external-priority patent/KR102645441B1/ko
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Priority to CN201880077914.4A priority Critical patent/CN111447911A/zh
Publication of WO2019108008A1 publication Critical patent/WO2019108008A1/fr

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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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 disclosure relates to emulsified compositions comprising a substance having a positive potential, an amphiphilic anisotropic powder, and a substance having a negative potential.
  • an aqueous emulsion is formed by mixing an aqueous phase with an aqueous phase according to the HLB (Hydrophile-Lipophile Balance) value of the surfactant to emulsify the internal phase and the external phase.
  • HLB Hydrophile Balance
  • the size and shape of the spherical fine particles made of the polymer are controlled according to the manufacturing method, and thus the application possibility is expanded.
  • One of its applications is Pickering emulsion which can form stabilized macroporous particles using micro spherical particles.
  • O / W emulsified particles are formed at a contact angle of 90 ° or more, and W / O emulsion particles are formed at a temperature of 90 ° or less depending on the degree of hydrophilicity / hydrophobicity of the spherical particles.
  • a problem to be solved by the present invention is to provide an emulsified composition excellent in emulsion stability.
  • a problem to be solved by the present invention is to provide an emulsified composition including an amphiphilic anisotropic powder and having excellent stability at a low viscosity with time.
  • the present invention provides an emulsified composition
  • the hydrophilic one of the shells comprises a functional group
  • the emulsion composition comprises two phases, and the phases have mutually opposite electric potentials, Thereby providing an emulsified composition.
  • the present invention can provide an emulsified composition having excellent low viscosity emulsion stability.
  • the present invention can provide an emulsified composition having an excellent stability at a low viscosity including an amphiphilic anisotropic powder.
  • FIG. 1 is a schematic diagram for forming an amphiphilic anisotropic powder according to an embodiment of the present invention.
  • FIG. 2 shows the pH-dependent change of the aqueous phase of hexyldecyl myristoyl methyl aminopropionate (HEXYLDECYL MYRISTOYL METHYL AMINOPROPIONATE) according to an embodiment of the present invention.
  • FIG. 3 is a graph showing the difference in thin film formation according to the degree of neutralization of the increment agent of hexyldecyl myristoyl methyl aminopropionate (HEXYLDECYL MYRISTOYL METHYL AMINOPROPIONATE) according to an embodiment of the present invention.
  • Fig. 4 shows the results of comparing emulsion formation differences according to the presence or absence of electric potential of the oil phase of the compositions of Reference Example 10 and Reference Example 9.
  • Fig. The left side is the reference example 10, and the right side is the reference example 9.
  • FIG. 5 is a graph showing that the (-) z-potential value of the amphiphilic anisotropic powder shifts in the (+) z-potential direction while bonding with the emollient, confirming that the amphiphilic anisotropic powder binds with the emollient Lt; / RTI >
  • the red color in the lower graph is the z-potential value when bound with hexyldecyl myristoyl methylaminopropionate under the same conditions as the amphoteric anisotropic powder, and the green is the value when the pH is adjusted.
  • 6A is a schematic view of an emulsified particle using only a substance having a positive potential and a substance having a negative potential.
  • FIG. 6B is a schematic diagram of emulsified particles of an emulsified composition comprising a substance having a positive potential, a substance having a negative potential, and an amphiphilic anisotropic powder according to an embodiment of the present invention.
  • FIG. 6B is a schematic diagram of emulsified particles of an emulsified composition comprising a substance having a positive potential, a substance having a negative potential, and an amphiphilic anisotropic powder according to an embodiment of the present invention.
  • 7A is a photomicrograph of the emulsified particles after 4 weeks of preparation of the composition using only the carbomer of Comparative Example 1 and hexyldecyl myristoyl methyl aminopropionate (HEXYLDECYL MYRISTOYL METHYL AMINOPROPIONATE).
  • FIG. 7B is a photomicrograph of the emulsified particles after four weeks of preparation of a composition containing the carbomer, hexyldecyl myristoyl methyl aminopropionate (HEXYLDECYL MYRISTOYL METHYL AMINOPROPIONATE) and amphipathic anisotropic powder of Example 1.
  • FIG. 7B is a photomicrograph of the emulsified particles after four weeks of preparation of a composition containing the carbomer, hexyldecyl myristoyl methyl aminopropionate (HEXYLDECYL MYRISTOYL METHYL AMINOPROPIONATE) and amphipathic anisotropic powder of Example 1.
  • FIG. 7B is a photomicrograph of the emulsified particles after four weeks of preparation of a composition containing the carbomer, hexyldecyl myristoyl methyl aminopropionate (HEXYLDECYL MYRISTOY
  • FIG. 7C is a photomicrograph of the emulsified particles after 4 weeks of preparation of the composition containing the carbomer of Comparative Example 2.
  • an emulsified composition comprising a substance having dislocations, and a double spiroid type polymeric amphipathic powder comprising a hydrophilic one-side and a hydrophobic one, wherein the powder has a hydrophobic side partially embedded in the hydrophilic one side
  • the hydrophilic one of the shells comprises a functional group
  • the emulsion composition comprises two phases, and the phases have mutually opposite electric potentials.
  • the substance having the dislocation may include at least one of a substance having a positive potential and a substance having a negative potential.
  • the present invention provides an emulsified composition comprising a substance having a positive potential, a substance having a negative potential, and a bispolide amphiphilic anisotropic powder comprising a hydrophilic one-side and a hydrophobic one, wherein the hydrophilic one of the shells comprises a functional group, the emulsion composition comprises two phases, and the phase comprises an emulsifying composition having a mutual potential opposite to that of the other, .
  • the two phases may include an aqueous phase and an oil phase.
  • the emulsion composition may include, for example, W / O, O / W phase, but is not limited thereto.
  • the interface is stabilized due to interactions between charges, so that the coagulation, fusion, or creaming of the emulsion particles in the emulsion composition can be prevented.
  • the substance having the positive potential may include an emollient
  • the substance having the negative potential may include an increasing agent
  • the emulsifying composition may be in water or in water.
  • the emulsified composition may be a water-in-oil type.
  • the substance having the positive potential can interact with the substance having the negative potential to form a film. Since the two phases contain a material having opposite potentials, the two phases exhibit opposite potentials and exhibit charge interactions at the interface between the two phases.
  • Figure 6a shows the formation of regions (denoted in the figure as ion charge interaction zones) in the formulations containing materials having opposite potentials in two phases, representing interactions between the charges at the interface. It is possible to exhibit excellent interfacial stability by the film formed in the region showing the interaction between the charges.
  • FIG. 6B is a schematic diagram of a formulation in which an amphiphilic anisotropic powder is present in a film formed in a region showing charge-charge interaction.
  • the amphipathic anisotropic powder can form stable emulsified particles by having the hydrophobic part and the hydrophilic part have different directions to the interface.
  • the emulsion particle formed by introducing an amphiphilic anisotropic powder into the interfacial membrane increases the thickness of the interfacial membrane to several hundreds nm, while the interfacial film formed by the general molecular-level surfactant forms a dynamic emulsion state. A solid interfacial film is formed.
  • an amphiphilic anisotropic powder is introduced into the stabilized interface through the interaction with the charge, so that a more stable emulsified composition can be formed.
  • the amphiphilic anisotropic powder may be present at the interface with the substance having the disposition.
  • an amphiphilic anisotropic powder may be combined with a substance having a positive potential.
  • the emulsion stability can be improved through the formation of the interfacial film, and the emulsion composition according to the present invention can have more stability.
  • the emulsified particles according to the present invention can form a stable emulsified formulation in a wide range of viscosity and can provide a soft feeling feeling with a low viscosity.
  • the substance having a positive potential can be any substance exhibiting a positive potential, but can include, for example, a emollient having a positive potential, and can include, for example, a compound containing an amine group .
  • the substance having a positive potential may include at least one selected from an aliphatic amine compound, an aromatic amine compound and an amine group-containing silicone compound.
  • the compound containing an amine group may be, for example, a compound having a functional group such as -N ⁇ , -NH-, -NH 2, or the like.
  • a compound having a functional group such as an aliphatic amine compound, an aromatic amine compound, but are not limited to, species.
  • the compound containing an amine group may be an alkylamine containing a linear or branched alkyl group having 6 to 30 carbon atoms, an aliphatic amine compound such as an alkanolamine containing a linear or branched alkanol group having 6 to 30 carbon atoms, , aromatic amine compounds such as o-toluidine, 2,4,6-trimethylaniline, anisidine and N-methylaniline, bisamodimethicone, amodimethicone, aminopropyldimethicone ( aminopropyl dimethicone), and the like.
  • the substance having the positive potential may be contained in the oil phase of the emulsified composition.
  • the emulsified composition may contain 0.01% to 75% by weight of the substance having the positive potential relative to the total weight of the composition.
  • the material having a positive potential is included in the above range, emulsion stability can be excellent, and stability with time can be excellent especially at a low viscosity.
  • the substance having a negative electric potential may be any substance exhibiting a negative electric potential, but may include an aging agent having a negative electric potential, for example, an anionic polymer.
  • the anionic polymer compound may be, for example, a polymer compound having a carboxylic acid group, a sulfonic acid group, a sulfuric acid ester group, or a phosphoric acid ester group as a functional group.
  • a polymer compound having a carboxylic acid group, a sulfonic acid group, a sulfuric acid ester group, or a phosphoric acid ester group as a functional group may be selected from an acrylic acid polymer, a polysaccharide polymer and a sulfonic polymer But is not limited thereto.
  • the anionic polymer compound may be selected from the group consisting of polyacrylic acid, polymethacrylic acid, polymethylmethacrylic acid, methylmethacrylate-acrylic acid copolymer, vinylpyrrolidone-acrylic acid copolymer, hydroxyethyl acrylate / sodium acrylate
  • An acrylic acid polymer such as a hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer, an acrylate / C10-30 alkyl acrylate cross polymer (ACRYLATES / C10-30 ALKYL ACRYLATE CROSSPOLYMER), a carbomer
  • Polysaccharide polymer compounds such as alginic acid, pectin and polygalacturonic acid
  • sulfonic acid-based polymer compounds such as polystyrene sulfonic acid.
  • hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer acrylate / C10-30 alkyl acrylate crosspolymer (ACRYLATES / C10-30 ALKYL ACRYLATE CROSSPOLYMER), acrylate / And carbomers may be used.
  • the material having a negative potential may be a carbomer.
  • the material having a negative potential may have a pH of 7 or less and lower the pH of the overall composition.
  • the carbomer may lower the pH of the overall composition.
  • the substance having the negative electric potential may be contained in the water phase of the emulsified composition.
  • the emulsified composition may contain 0.01 to 10% by weight of the substance having the negative potential with respect to the total weight of the composition. Preferably from 0.1 to 0.4% by weight, based on the total weight of the composition. Within this range, the emulsified composition may have excellent stability at low viscosity.
  • the emulsified composition may have a pH of 7 or less, for example, a pH of 3 to 7. Within this range, the emulsified composition may have excellent stability at low viscosity.
  • the emulsified composition may have a pH of less than 7, less than pH 6.5, less than pH 6, less than pH 5.5, less than pH 5, less than pH 4.5, less than pH 4.0, or less than pH 3.5, PH 4.0 or higher, pH 4.5 or higher, pH 5.0 or higher, pH 5.5 or higher, pH 6.0 or higher, or pH 6.5 or higher.
  • the magnitude of the positive potential of a substance having a positive potential may vary depending on the pH of the composition, for example, the lower the pH, the larger the potential.
  • the bispulo-type polymeric amphipathic anisotropic powder may be present at the interfaces of the two phases.
  • the amphiphilic anisotropic powder may be a double-sphere type polymeric amphipathic anisotropic powder consisting of a hydrophilic one-side and a hydrophobic one.
  • the powder may have a structure in which the hydrophobic other part partially penetrates into the inside of the hydrophilic one to form a hydrophilic one of the cores, and the hydrophilic one may include a functional group.
  • the amphiphilic anisotropic powder includes a hydrophilic one (first polymer spoloid) and a hydrophobic other (second polymer spoloid), the hydrophilic one having a core-shell structure, the hydrophobic one having a hydrophilic one- At least partially penetrating into the inside of the hydrophilic core to form a hydrophilic one of the cores, and the hydrophilic one shell may contain a functional group.
  • FIG. 1 is a schematic view showing the principle of formation of an amphiphilic anisotropic powder according to an embodiment of the present invention.
  • the core of the first polymer spolide may be formed through the shell of the first polymer spolide and may be grown to form a second polymer spoloid by the above manufacturing method.
  • the powder may be in the form of a double sparoid, that is, a three-dimensional nephroid having a shape in which two spheroids are combined, and a symmetrical shape, asymmetric snowman snowman-shaped or asymmetric inverse snowman shape.
  • the shape of the snowman means that the first and second polymer spheroids having different sizes are combined.
  • the spheroid may be, for example, a sphere, a globoid, or an oval shape, and may have a major axis length in microns or nanometers based on the longest length in the body cross-section. have.
  • the hydrophilic one may be a core-shell structure in which the core is made of the same polymer as the hydrophobic base, and the hydrophilic one and the hydrophobic one may each take one spoloid shape of the double spoil.
  • the binding portion between the two sphereoids of the double sphere may have a continuous structure from the hydrophilic core to the hydrophobic one.
  • the hydrophilic one-side core and the hydrophobic one include a vinyl polymer
  • the hydrophilic one-side 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, and may be, for example, 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 functional group-containing monomer may be a siloxane-containing (meth) acrylate, and specifically includes 3- (trimethoxysilyl) propyl acrylate, 3- (trimethoxysilyl) propyl methacrylate, vinyl Triethoxysilane, vinyltrimethoxysilane, or a mixture thereof.
  • the hydrophilic one-side shell may further include a hydrophilic functional group.
  • the hydrophilic functional group may be a functional group having a negative or positive potential or a PEG (polyethylene glycol) group, and may be a carboxylic acid group, a sulfonic group, a phosphate group, an amino group, an alkoxy group, an ester group, an acetate group, a polyethylene glycol group, And a hydroxyl group.
  • PEG polyethylene glycol
  • the hydrophilic one-side shell may further include a sugar-containing functional group.
  • the functional group containing the sugar is selected from the group consisting of N- ⁇ N- (3-triethoxysilylpropyl) aminoethyl ⁇ gluconamide, N- (3-triethoxysilylpropyl) - (3-triethoxysilylpropyl) aminoethyl ⁇ -oligo-hyaluronamide, and the like.
  • the amphiphilic anisotropic powder may have a particle size of 100 to 1500 nm.
  • the amphiphilic anisotropic powder may have a particle size of 100 to 500 nm, or 200 to 300 nm.
  • the amphiphilic anisotropic powder preferably 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, 1200 nm or more, 1200 nm or more, 1300 nm or more or 1400 nm or more and 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 and 800 nm or less , 700 nm or less, 600 nm or less.
  • the particle size of the amphiphilic anisotropic powder herein is the maximum length measured as the longest length of the powder particle.
  • the particle size range of the amphiphilic anisotropic powder herein means that at least 95% of the amphipathic anisotropic powder present in the composition falls within this range.
  • the amphiphilic anisotropic powder may be prepared by polymerizing a first monomer to prepare a core of a first polymer spoloid, coating the core of the first polymer spoloid to form a core- And preparing an amphiphilic anisotropic powder in which the second polymer spolide is formed by reacting the first polymer spolide of the core-shell structure with the first monomer.
  • FIG. 1 is a schematic view showing the principle of formation of an amphiphilic anisotropic powder according to an embodiment of the present invention.
  • the core of the first polymer spolide may be formed through the shell of the first polymer spolide and may be grown to form a second polymer spoloid by the above manufacturing method.
  • the amphiphilic anisotropic powder is prepared by (1) stirring the first monomer and the polymerization initiator to prepare a core of the first polymer spolide; (2) stirring the prepared core of the first polymer spolide with a monomer containing a first monomer, a polymerization initiator and a functional group to prepare a first polymer spolide having a coated core-shell structure; (3) preparing an amphiphilic anisotropic powder in which the second polymer spolide is formed by stirring the first polymer spoloid of the prepared core-shell structure with the second monomer and the polymerization initiator.
  • stirring may be rotary stirring. It is preferable to rotate and stir because chemical mechanical modification and homogeneous mechanical mixing are required for producing uniform particles.
  • the rotational stirring may be performed in a cylindrical rotating reactor, but the rotational stirring method is not limited thereto.
  • the design inside the reactor has a great influence on powder formation.
  • the size and location of the baffles in the cylindrical rotating reactor and the degree of spacing between the impeller and the baffles greatly influence the uniformity of the particles produced. It is desirable to minimize the interval between the blades of the inner wing and the impeller to equalize the convection flow and the strength thereof, and to feed the powder reaction liquid below the wing length and to maintain the impeller rotation speed at a high speed.
  • 200 rpm, and the length to diameter ratio 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 be varied in proportion to the reaction capacity.
  • the material of the cylindrical rotating reactor may be ceramics, glass, etc., and the temperature at the time of stirring is preferably 50 to 90 ° C.
  • the simple rotation method is capable of producing uniform particles, and is a low energy method requiring less energy and maximizing the reaction efficiency, enabling mass production.
  • the conventional tumbling method in which the reactor itself rotates requires high energy and restricts the size of the reactor since the entire reactor must be tilted at a constant angle and rotated at high speed.
  • the amount produced due to reactor size limitations was also limited to small quantities of the order of several hundreds of milligrams to several grams, making them unsuitable for mass production.
  • the first monomer and the second monomer may be the same or different, and may be specifically vinyl monomers.
  • the first monomer added in the step (2) is the same as the first monomer used in the step (1), and 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, a peroxide type, an azo type, or a mixture thereof. Ammonium persulfate, sodium persulfate and potassium persulfate may also be used.
  • the first monomer and the polymerization initiator may be mixed at 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 in the step (1) 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 first polymer spoil size adjustment in the initial stage (1), and the first polymer spoil size can be adjusted according to the weight ratio of the first monomer, the polymerization initiator, and the stabilizer. Further, by mixing at the weight ratio within the above range, the shape and uniformity of the anisotropic powder can be remarkably increased.
  • the stabilizer may be an ionic vinyl monomer, and specifically sodium 4-vinylbenzene sulfonate may be used. Stabilizers prevent swelling of the resulting particles and provide positive or negative charge on the powder surface to electrostatically prevent interactions (bonds) during grain formation.
  • 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: 2 to 4, when the amphiphilic anisotropic powder has a size of 200 to 250 nm. 1 < / RTI > polymer spolide.
  • the weight ratio of the first monomer, the polymerization initiator and the stabilizer is in the range of 225 to 240: 1: 1 to 3, specifically 230 to 235: 1: 1 to 3 , ≪ / RTI > the first polymeric spheroids.
  • 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 ≪ / RTI >
  • the amphiphilic anisotropic powder having an asymmetric snowman shape is preferably an amorphous powder having 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 Can be prepared from polymeric sphereoids.
  • the amphiphilic anisotropic powder having an asymmetric reverse snowman shape is preferably an amphipathic powder having a weight ratio of the first monomer, the polymerization initiator and the stabilizer of 100 to 140: 1: 1 to 5, specifically 110 to 130: 1: 2 to 4 1 < / RTI > polymer spolide.
  • the monomer containing a functional group in the step (2) may be a siloxane-containing (meth) acrylate.
  • a siloxane-containing (meth) acrylate examples thereof include 3- (trimethoxysilyl) propyl acrylate, 3- (trimethoxysilyl) Methacrylate, vinyltriethoxysilane, vinyltrimethoxysilane, or a mixture 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. In another aspect, the monomer containing the first monomer, the polymerization initiator and the functional group may be mixed at a weight ratio of 150 to 300: 1: 6 to 40.
  • the degree of coating can be controlled according to the weight ratio, and the shape of the amphipathic anisotropic powder is determined according to the degree of coating, and when the weight ratio is adjusted, the coating thickness is increased to about 10 to 30%, specifically about 20% And the coating is too thick, so that the pulverization does not proceed or the pulverization is proceeded well without the problem that the pulverization is too thin.
  • the uniformity of the anisotropic powder can be increased.
  • step (3) a part of the core of the first polymer spolide is protruded from the one side of the first polymer spolide of the core-shell structure through the shell and the protrusions are grown by the polymer of the second monomer, Can be formed.
  • 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 may be present in an amount of from 160 to 250: 1, or from 170 to 250: 1, or from 180 to 250: 1, or from 190 to 250: 1, or from 200 to 250: : 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 mixed in a weight ratio of 150: 250: 1: 0.001 to 5 by adding the second monomer and the polymerization initiator together with the stabilizer in the step (3).
  • Specific types of stabilizers are as described above.
  • the second monomer content may be 40 to 300 parts by weight when the weight of the first polymer spoil of the core-shell structure is 100 parts by weight. Specifically, when the second monomer content is 40 to 100 parts by weight when the first polymer spoil weight of the core-shell structure is 100 parts by weight, the asymmetric snowman type powder is obtained, and 100 to 150 parts by weight, or 110 to 150 parts by weight, When the weight is in the range of 150 to 300 parts by weight or in the range of 160 to 300 parts by weight, an asymmetric reverse snowman type powder is obtained. In addition, by mixing at the weight ratio within the above range, there is an effect that the uniformity of the anisotropic powder can be increased.
  • the step (3) may further include the step of (4) introducing a hydrophilic functional group into the produced 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 control agent.
  • the silane coupling agent is selected from the group consisting of (3-aminopropyl) trimethoxysilane, N- [3- (trimethoxysilyl) propyl] ethylenediamine, N- [3- (trimethoxysilyl) (Trimethoxysilyl) propyl] urea and 3 - [(trimethoxysilyl) propyloxy] -1,2 (trimethylsilyl) Propanediol, and specifically may be at least one selected from the group consisting of N- [3- (trimethoxysilyl) propyl] ethylenediamine.
  • the silane coupling agent may be added 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 the step (3). Within this range, hydrophilization can be appropriately performed.
  • reaction modifier may be ammonium hydroxide.
  • reaction modifier may be added in an amount of 85 to 115 parts by weight, for example, 90 to 110 parts by weight based on 100 parts by weight of the anisotropic powder prepared in the step (3).
  • hydrophilization can be appropriately performed.
  • the step (3) is followed by (4) a step of introducing a sugar-containing functional group into the produced anisotropic powder .
  • the functional group containing sugar is not limited thereto, but may be introduced using a sugar-containing silane coupling agent and a reaction control agent.
  • the sugar-containing silane coupling agent is selected from the group consisting of N- ⁇ N- (3-triethoxysilylpropyl) aminoethyl ⁇ gluconamide, N- (3-triethoxysilylpropyl) And N- ⁇ N- (3-triethoxysilylpropyl) aminoethyl ⁇ -oligo-hyaluronamide.
  • the reaction modifier may be ammonium hydroxide.
  • reaction modifier may be added in an amount of 85 to 115 parts by weight, for example, 90 to 110 parts by weight based on 100 parts by weight of the anisotropic powder prepared in the step (3).
  • the introduction of a sugar-containing functional group within the above range can be suitably performed.
  • the preparation of the amphiphilic anisotropic powder according to the above method does not use a cross-linking agent, so there is no production entanglement.
  • the yield is high and uniform, and mass production is easier than the tumbling method using a simple agitation method.
  • the size of the emulsified particles may be from 1 ⁇ m to 100 ⁇ m in average particle size, for example from 10 ⁇ m to 30 ⁇ m.
  • the average particle diameter is 1 ⁇ ⁇ or more, 2 ⁇ ⁇ or more, 3 ⁇ ⁇ or more, 4 ⁇ ⁇ or more, 5 ⁇ ⁇ or more, 6 ⁇ ⁇ or more, 7 ⁇ ⁇ or more, 8 ⁇ ⁇ or more, At least 15 ⁇ , at least 16 ⁇ , at least 17 ⁇ , at least 18 ⁇ , at least 19 ⁇ , at least 20 ⁇ , at least 21 ⁇ , at least 22 ⁇ , at least 23 ⁇ , at least 24 ⁇ At least 25 ⁇ , at least 26 ⁇ , at least 27 ⁇ , at least 28 ⁇ , at least 29 ⁇ , at least 30 ⁇ , at least 35 ⁇ , at least 40 ⁇ , at least 45 ⁇ , at least 50 ⁇ , at least 55 ⁇ ,
  • the average particle diameter may be 100 ⁇ ,
  • the average particle diameter of the emulsified particles means an average value of the diameter of a single particle.
  • the particle diameter of the emulsion particle is not uniform, and the emulsion particle having a particle diameter in the wide range of 0.1 to 2000 ⁇ m coexists.
  • the mean particle diameter of the macro emulsion particles may be, for example, 20 mu m.
  • the composition may comprise the amphiphilic anisotropic powder in an amount of 0.01 to 10% by weight, preferably 0.1 to 1% by weight, based on the total weight of the composition. More specifically, it is preferable that the content of the inorganic filler is 0.01 wt% or more, 0.1 wt% or more, 0.2 wt% or more, 0.3 wt% or more, 0.4 wt% or more, 0.5 wt% or more, 0.6 wt% or more, 0.7 wt% or more, 0.8 wt% %, Up to 9 wt.%, Up to 8 wt.%, Up to 7 wt.%, Up to 6 wt.%, Up to 5 wt.%, Up to 4 wt.%, Or up to 3 wt.%, Or less, 2 wt% or less, or 1 wt% or less.
  • the composition may comprise the amphiphilic anisotropic powder in an amount of 0.1% to 20% by weight, for example, 0.1% to 1%, and in one embodiment 0.5% by weight based on the total weight of the composition .
  • Stable emulsion particles can be formed within the above range, and emulsion particles having an appropriate size can be formed.
  • the ratio of the substance having the positive potential to the substance having the negative potential: amphiphilic anisotropic powder can be included in a weight ratio of 100: 1 to 20: 1-10.
  • the weight ratio is 100: 1.5-18: 1.2-9, 100: 2-16: 1.4-8, 100: 2.5-14: 1.6-7, 100: 3-12: 1.8-6, 100: 3.5 -10: 2-5, 100: 4-8: 2.2-4, or 100: 4.5-6: 2.4-4 and the weight ratio is 100: 1.5-20: 1-9, 100: 20: 1-8, 100: 2.5-20: 1-7, 100: 3-20: 1-7, 100: 3.5-20: 1-6, 100: 4-20: 1-5, or 100: 4.5 -20: 1-4, and the weight ratio is 100: 1-18: 2-10, 100: 1-16: 3-10, 100: 1-14: 4-10, 100: 1-12 : 5-10, 100: 1-10: 6-10, 100: 1-8: 7-10.
  • the emulsifying composition may comprise a pH adjusting agent.
  • the water phase of the emulsified composition may further comprise an acid.
  • the acid may be included in any acid used in cosmetics.
  • the acid may be one or more selected from the group consisting of lactic acid, glycolic acid, ethyl ascorbic acid, ascorbic acid, and glutamic acid. But is not limited thereto.
  • the viscosity of the composition may be 100-100,000 cps, for example, the viscosity of the composition may be 2,000-15,000 cps. Since the composition according to this embodiment does not require stabilization through an incremental increase, it is possible to provide a composition having a wide range of viscosity regardless of viscosity.
  • the viscosity of the composition can be measured using a BROOKFIELD Viscometer.
  • the viscosity of the composition may be controlled by the content of a substance having a positive potential or the content of a substance having a negative potential, for example the composition may have a viscosity of at least 15000 cps.
  • the composition may have a viscosity of, for example, greater than 200 cps, greater than 300 cps, greater than 400 cps, greater than 500 cps, greater than 600 cps, greater than 700 cps, greater than 800 cps, greater than 900 cps, greater than 1000 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, at least 1800 cps, at least 1900 cps, at least 2000 cps, at least 2100 cps, at least 2200 cps, at least 2300 cps, More than 2400 cps, greater than 2500 cps, greater than 2600 cps, greater than 2700 cps, greater than 2800 cps, greater than 2900 cps, greater than 3000 cp
  • the composition may have excellent emulsion stability at a viscosity of 100-100,000 cps, and in particular, the composition may have a low viscosity at a low viscosity of 2000-15000 cps, for example at a low viscosity of 3000-10000 cps.
  • the composition may further comprise a surfactant for emulsification.
  • a surfactant for emulsification examples include lauryl PEG-9 polydimethylsiloxyethyl dimethicone, cyclopentasiloxane * PEG-10, and the like.
  • the surfactant examples include, but are not limited to, Dimethicone * Distearimonium Hectorite, Cetyl PEG.PPG-10/1 Dimethicone (Cetyl Dimethicone Copolyol; Cetyl PEG.PPG-10/1 Dimethicone (Cetyl Dimethicone * Copolyol, etc.), arachidyl alcohol / behenyl alcohol / arachidyl glucoside (ARACHIDYL ALCOHOL / BEHENYL ALCOHOL / ARACHIDYL GLUCOSIDE), cetearyl alcohol * CETEARYL ALCOHOL * CETEARYL GLUCOSIDE), C14-22 alcohol * C12-20 alkyl glucoside (C14-22 ALCOHOLS * C12-20 ALKYL GLUCOSIDE), glyceryl stearate * PEG-100 stearate (Glyceryl Stearate * PEG- W You The like of a surfact
  • the surfactant may be included in an amount of 0 to 20% by weight, 0 to 10% by weight, or 0 to 5% by weight based on the total weight of the composition. In this embodiment, it is possible to stabilize the emulsified formulation while containing a small amount of surfactant.
  • the composition according to 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 may be in the form of a suspension, a microemulsion, a microcapsule, a microgranule or an ionic (liposome) and a non-ionic follicular dispersion, or a cream, a skin, a lotion, a powder, an ointment, a spray, May be provided in the form of a stick. It can also be used in the form of a foam or in the form of an aerosol composition further containing a compressed propellant. These compositions may be prepared according to conventional methods in the art.
  • the cosmetic composition according to embodiments of the present invention may be in the form of powders, fatty substances, organic solvents, solubilizers, thickeners, gelling agents, softeners, antioxidants, suspending agents, stabilizers, foaming agents, , Water, ionic or nonionic emulsifiers, fillers, sequestering agents, chelating agents, preservatives, vitamins, barrier agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or cosmetics And any other ingredients used, such as cosmetics or adjuvants commonly used in the field of dermatology. Such adjuvants are introduced in amounts commonly used in the cosmetics or dermatological fields.
  • 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.
  • Production Examples 1-1 to 1-4 were prepared according to the composition shown in Table 1 below. Specific methods are described below.
  • SVBS Sodium vinyl benzene sulfonate (stabilizer)
  • PS Polystyrene (polymer bead)
  • AIBN Azobisisobutyronitrile (polymerization initiator)
  • styrene as a monomer
  • 1.0 g of sodium 4-vinylbenzenesulfonate as a stabilizer
  • 0.5 g of azobisisobutyronitrile (AIBN) as a polymerization initiator were mixed in a water bath at 75 DEG C For 8 hours.
  • the reaction was stirred in a cylindrical rotating reactor.
  • the cylindrical rotating reactor was 11 cm in diameter, 17 cm in height, made of glass, and rotated at a speed of 200 rpm.
  • the emulsion composition of the present invention was examined for changes in the physical properties of a substance having a positive potential (emollient) depending on the pH of the aqueous phase, and the effect of the type of acid affecting the pH was examined.
  • the substance having a positive potential was purchased from Nippon Emulsion Co., Ltd., and HEXYLDECYL MYRISTOYL METHYL AMINOPROPIONATE, which is a trade name AMITER MA-HD, was used, Lithospermi Radix ) extract And hexyldecyl myristoyl methylaminopropionate were used. Water, glycolic acid, and ethyl ascorbic acid were used as the water phase. Extracts of B. pertussis were used as a reddish oil-soluble material to facilitate visual confirmation of film formation and emulsification. There is no influence on the formation of the formulations even when the pigment is changed to another oil-soluble dye. When the layer separation occurs, the red layer is identified with a bright red color, and when the emulsification occurs, it appears to be light pink.
  • each raw material of acid was put into the water as shown in Table 2, prepared by titrating to the corresponding pH, and the oil phase and the water phase were hand-mixed.
  • the layer separation is performed by the behavior of a substance having a general positive potential (Referential Examples 1 and 3, (1) and (3) in FIG. 2) It was confirmed that the tertiary amine moiety of the substance having a positive electric potential has a positive electric potential through the base reaction and serves as a surfactant (Reference Examples 2 and 4, (2) and (4) in FIG. 2). Further, it was confirmed that there was no influence depending on the type of acid.
  • 0.1 wt% of carbomer as a substance having a negative potential was added to the aqueous phase.
  • tromethamine was neutralized with neutralizing agent to pH 3, 4, 5, and 6 in each reference example. After neutralization, hexyldecyl myristoyl methyl aminopropionate was slowly poured without mixing to observe the thin film layer on the surface.
  • the positive potential of the substance having a positive potential differs depending on the pH level.
  • Positive potentials of counter-positively charged positive potentials which can bind to carbomers with negative potential, increase with decreasing pH, and thus the difference in the degree of formation of the thin film layer due to charge interactions . It was confirmed that a transparent thin film was formed at pH 6 (Reference Example 8), from which it is expected that the thin film layer becomes unstable in a formulation of pH 7 or more.
  • Comparative Example 1 was prepared by mixing a squalane extract with a common oil having no dislocation.
  • Example 1 emulsion helixdecyl myristoyl methyl aminopropionate having a positive potential varying with pH, The extracts were mixed and prepared.
  • Water containing the amphiphilic anisotropic powder prepared in Preparation Example 1-3 was prepared as an aqueous phase, and the aqueous phase was pH 5 without any pH adjustment.
  • the oil phase was added to the liquid phase (pH 5) of the amphiphilic anisotropic powder without pH adjustment of the water phase and observed by hand mixing. A photograph of the composition is shown in FIG.
  • the Z-potential of the amphiphilic anisotropic powder and the change in the numerical value after the binding of the amphiphilic anisotropic powder and hexyldecyl myristoyl methyl aminopropionate are shown in FIG. Specifically, the composition containing the amphiphilic anisotropic powder in the composition of Table 5 and the composition containing the amphiphilic anisotropic powder and hexyldecyl myristoyl methylaminopropionate were measured for Z-potential using a Zetasizer (Malvern) Respectively.
  • Figure 5 shows that the (-) z-potential value of the amphiphilic anisotropic powder itself (upper graph) is lower than that of the amphiphilic anisotropic powder in the (+) direction while the amphiphilic anisotropic powder and hexyldecyl myristoyl methylaminopropionate bind in the lower graph. Which indicates the binding of the amphiphilic anisotropic powder to the emollient.
  • a formulation using only carbomer and hexyldecyl myristoyl methyl aminopropionate and a particle varying with an amphipathic anisotropic powder are compared and observed.
  • the viscosity of the emulsion composition prepared in the contents of Table 6 was measured at 30 ° C on the next day of manufacture using a viscosity meter (BROOKFIELD Viscometer, SPINDLE # 3, 12RPM, 30 ° C, the next day).
  • FIG. 7A, 7B, and 7C are photographs of micrographs of emulsion particles observed after the compositions of Comparative Example 1, Example 1, and Comparative Example 2 were stored at 30 DEG C for 4 weeks, respectively.
  • the emulsion formulations of Comparative Example 1 ) And the amphiphilic anisotropic powder of Example 1 (Fig. 7B) were the same formulation except that Example 1 contained 0.5 wt% of the amphiphilic anisotropic powder, and Comparative Example 2 (Fig. 7C) Powder, and positive displacement material.
  • Example 1 it was confirmed that the amphiphilic anisotropic powder is located at a site where the film is formed by the interaction between charges, and the particles are made large.
  • Comparative Example 2 did not achieve 4-week stability in the pilot scale, but Example 1 (Fig. 7B) in which amphipathic anisotropic powder was combined had 4000 cps and formed large particles, And it was confirmed that it has stability.

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Abstract

L'invention concerne une composition d'émulsion comprenant un matériau chargé positivement, un matériau chargé négativement, et une poudre polymère anisotrope amphiphile à double sphéroïde composée d'un côté à caractère hydrophile et d'un autre côté à caractère hydrophobe, la poudre possédant une structure dans laquelle le côté à caractère hydrophobe s'infiltre partiellement à l'intérieur du côté à caractère hydrophile pour former un noyau à caractère hydrophile, l'enveloppe à caractère hydrophile comprenant un groupe fonctionnel, et la composition d'émulsion comprenant deux phases, ces phases présentant des charges électriques opposées.
PCT/KR2018/015069 2017-11-30 2018-11-30 Composition d'émulsion comprenant une poudre anisotrope amphiphile et présentant une stabilité améliorée WO2019108008A1 (fr)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
JPH09143027A (ja) * 1995-11-29 1997-06-03 Ajinomoto Co Inc 乳化化粧料の製造方法
JP2004238367A (ja) * 2003-02-07 2004-08-26 Kao Corp 油中水型乳化組成物
KR20150138096A (ko) * 2014-05-30 2015-12-09 (주)아모레퍼시픽 양친매성 이방성 분체를 포함하는 화장료 조성물 및 이의 제조방법
JP2017518342A (ja) * 2014-06-25 2017-07-06 ザ プロクター アンド ギャンブル カンパニー アミドアミンカチオン性界面活性剤及び付着ポリマーを含み、低いｐＨ値を有する、ヘアコンディショニング組成物
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JP2004238367A (ja) * 2003-02-07 2004-08-26 Kao Corp 油中水型乳化組成物
KR20150138096A (ko) * 2014-05-30 2015-12-09 (주)아모레퍼시픽 양친매성 이방성 분체를 포함하는 화장료 조성물 및 이의 제조방법
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