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WO2025169711A1 - Particules de résine biodégradable et leur utilisation - Google Patents

Particules de résine biodégradable et leur utilisation

Info

Publication number
WO2025169711A1
WO2025169711A1 PCT/JP2025/001723 JP2025001723W WO2025169711A1 WO 2025169711 A1 WO2025169711 A1 WO 2025169711A1 JP 2025001723 W JP2025001723 W JP 2025001723W WO 2025169711 A1 WO2025169711 A1 WO 2025169711A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin particles
mass
resin
less
biodegradable resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/001723
Other languages
English (en)
Japanese (ja)
Inventor
隆司 本村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Kasei Co Ltd
Original Assignee
Sekisui Kasei Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sekisui Kasei Co Ltd filed Critical Sekisui Kasei Co Ltd
Publication of WO2025169711A1 publication Critical patent/WO2025169711A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K8/85—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/16—Powdering or granulating by coagulating dispersions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present invention relates to biodegradable resin particles and their uses.
  • Resin particles taking advantage of their large specific surface area and particle structure, are used to modify and improve various materials.
  • Major applications include compounding agents for cosmetics such as foundations, antiperspirants, and scrubs; matting agents for paints; rheology modifiers; antiblocking agents; slipping agents; light diffusing agents; and various agents for medical diagnostic testing; as additives for molded articles such as automotive materials and building materials.
  • resin particles include urethane, acrylic, silicone, and polyethylene.
  • Patent Document 1 pulverization method
  • Patent Document 2 solvent dissolution precipitation method, in which the material is dissolved in a solvent at high temperature and then cooled to precipitate, or dissolved in a solvent and then precipitated by adding a poor solvent
  • Patent Document 3 emulsification method, in which the material is heated and stirred in an aqueous phase containing a polyhydric alcohol fatty acid ester and a water-soluble polymer, and then cooled
  • the resin particles of Patent Document 1 when used in external preparations such as cosmetics, the resin particles of Patent Document 1 have issues such as not being spherical and not achieving a small particle size, and further improvements are required in terms of spreadability on the skin. Furthermore, the resin particles obtained in Patent Document 2 are relatively spherical, but have the issue of not achieving a small particle size. Furthermore, the porous surface makes the particles brittle and results in low stability.
  • the resin particles of Patent Document 3 are spherical, but because they are water-absorbent, the resin particle surface becomes hydrophilic, posing an issue of insufficient makeup wear when used in cosmetics such as powder foundations.
  • the problem that the present invention aims to solve is to provide biodegradable resin particles that are highly hydrophobic and have excellent spreadability and compatibility with the skin, a topical agent containing said resin particles, a coating material containing said resin particles, a resin composition containing said resin particles, and an anti-blocking agent containing said resin particles.
  • the biodegradable resin particles of the present invention have a contact angle of 70° or more.
  • the lower limit of the contact angle of the biodegradable resin particles is preferably 75° or more, more preferably 80° or more, and even more preferably 85° or more.
  • the upper limit of the contact angle of the biodegradable resin particles is not particularly limited, but can be, for example, 130° or less.
  • the range of the contact angle of the biodegradable resin particles of the present invention can be preferably 75° or more and 130° or less, more preferably 80° or more and 130° or less, even more preferably 80° or more and 120° or less, even more preferably 85° or more and 120° or less, and particularly preferably 90° or more and 120° or less.
  • the biodegradable resin particles of the present invention have a circularity of 0.90 or more and 1.00 or less.
  • the lower limit of the circularity of the biodegradable resin particles is preferably 0.91 or more, more preferably 0.93 or more, and the upper limit of the circularity of the biodegradable resin particles is preferably 0.99 or less.
  • the circularity of the biodegradable resin particles of the present invention can be in the range of 0.90 to 0.99, 0.91 to 1.00, 0.91 to 0.99, 0.93 to 1.00, or 0.93 to 0.99.
  • the biodegradable resin particles of the present invention have a BET specific surface area of 0.1 m /g or more and 10 m /g or less.
  • the lower limit of the BET specific surface area of the biodegradable resin particles is preferably 0.2 m /g or more, and the upper limit of the BET specific surface area is preferably 3 m /g or less, more preferably 1 m /g or less.
  • the biodegradable resin particles of the present invention have a melting point in the range of, for example, 150°C or higher and 260°C or lower, preferably 155°C or higher and 260°C or lower, and more preferably 160°C or higher and 250°C or lower.
  • Components other than polyhydroxyalkanoate resin that may be contained in the biodegradable resin particles of the present invention include by-product components during resin production, various components used during resin particle production, and various components added to improve the properties of the resin particles. Examples include surfactants, solvents, flowability modifiers, UV absorbers, light stabilizers, pigments (e.g., extender pigments, colored pigments, metallic pigments, mica powder pigments, etc.), dyes, humectants, resins other than polyhydroxyalkanoate resins, fragrances, clay minerals, antiseptics/disinfectants, anti-inflammatory agents, antioxidants, pH adjusters (e.g., triethanolamine), and active pharmaceutical ingredients.
  • surfactants e.g., solvents, flowability modifiers, UV absorbers, light stabilizers, pigments (e.g., extender pigments, colored pigments, metallic pigments, mica powder pigments, etc.), dyes, humectants, resins other than polyhydroxyalkanoate resin
  • the method for producing the polyhydroxyalkanoate-based resin particles of the present invention is not particularly limited.
  • a production method comprising a step of heating a polyhydroxyalkanoate resin in an aqueous dispersion medium containing an emulsifier and the like to emulsify and disperse the polyhydroxyalkanoate resin, cooling the resulting mixture to obtain a dispersion of the polyhydroxyalkanoate resin, and then separating and drying the polyhydroxyalkanoate resin particles from the dispersion;
  • a production method (production method II) comprising the steps of: mixing a polyhydroxyalkanoate resin, a dispersion stabilizer, a good solvent for the polyhydroxyalkanoate resin, and a poor solvent for the polyhydroxyalkanoate resin to obtain a polyhydroxyalkanoate resin dispersion; separating polyhydroxyalkanoate
  • the emulsifier used in Production Method I is a compound capable of emulsifying the polyhydroxyalkanoate resin to form a suspension, and examples of the emulsifier include one or more selected from the group consisting of nonionic surfactants, anionic surfactants, sugars, amino acids, water-soluble polymers, and the like.
  • the following (i) to (iii) are used as emulsifiers: (i) a nonionic surfactant, (ii) nonionic surfactants and anionic surfactants; (iii) nonionic surfactants, anionic surfactants, and water-soluble polymers; It is preferable to use either one of the following.
  • nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxysorbitan fatty acid esters, polyoxyethylene alkylamines, glycerin fatty acid esters, and polyoxyethylene polyoxypropylene glycols, with nonionic surfactants having a polyoxyalkylene structure being preferred.
  • a nonionic surfactant having a polyoxyalkylene structure has a structure represented by the formula (2) in the molecule: (In formula (2), A is an alkylene group having 2 to 6 carbon atoms, and multiple A's may be the same or different, and m is the number of repeating units.) It is a nonionic surfactant having a polyoxyalkylene structure represented by the formula:
  • Nonionic surfactants having a polyoxyalkylene structure include, for example, polyoxyethylene alkyl ethers, polyoxypropylene alkyl ethers, polyoxybutylene alkyl ethers, polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene polyoxypropylene copolymers, polyoxyethylene alkylphenyl ethers, polyoxypropylene alkylphenyl ethers, polyoxyethylene polyoxypropylene alkylphenyl ethers, polyoxyethylene fatty acid esters, polyoxypropylene fatty acid esters, polyoxyethylene polyoxypropylene fatty acid esters, polyoxybutylene fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxypropylene Examples of the fatty acid ester include one or more selected from the group consisting of propylene glycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxypropylene sorbitan fatty acid esters, poly
  • the polyoxyethylene alkyl ether is preferably one or more selected from the group consisting of polyoxyethylene alkyl ethers, polyoxypropylene alkyl ethers, polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene polyoxypropylene copolymers, polyoxyethylene alkyl phenyl ethers, polyoxypropylene alkyl phenyl ethers, polyoxyethylene polyoxypropylene alkyl phenyl ethers, polyoxyethylene fatty acid esters, polyoxypropylene fatty acid esters, and polyoxyethylene polyoxypropylene fatty acid esters; more preferably one or more selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene polyoxypropylene copolymers, polyoxyethylene polyoxypropylene alkyl phenyl ethers, and polyoxyethylene polyoxypropylene fatty acid esters; and even more preferably one or more polyoxyethylene polyoxypropylene copoly
  • the amount of nonionic surfactant added is not particularly limited. It can be, for example, 0.5 parts by mass or more, preferably 1 part by mass or more, and can be, for example, 25 parts by mass or less, preferably 20 parts by mass or less, per 100 parts by mass of water.
  • Anionic surfactants include, for example, one or more selected from the group consisting of sulfate ester salts (alkyl sulfate ester salts, polyoxyalkylene alkyl ether sulfate ester salts, etc.), sulfonate salts (alkylbenzenesulfonate salts, alkanesulfonate salts, etc.), carboxylate salts (salts of fatty acids having 4 to 18 carbon atoms, alkenyl succinate salts, alkyl ether carboxylate salts, polymeric polycarboxylate salts, etc.), etc.
  • the amount of anionic surfactant added is not particularly limited. It can be, for example, 0.005 parts by mass or more, preferably 0.01 parts by mass or more, and can be, for example, 1.0 part by mass or less, preferably 0.5 part by mass or less, per 100 parts by mass of water.
  • sugars include one or more selected from the group consisting of natural polymers such as starch, alginic acid, alginates, locust bean gum, guar gum, gum arabic, xanthan gum, agar, carrageenan, crystalline cellulose, and pectin; and semi-synthetic polymers such as hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, propylene glycol alginate, and cationic modified starch.
  • natural polymers such as starch, alginic acid, alginates, locust bean gum, guar gum, gum arabic, xanthan gum, agar, carrageenan, crystalline cellulose, and pectin
  • semi-synthetic polymers such as hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, propylene glycol alginate, and cationic modified starch.
  • the amino acids may be, for example, one or more selected from the group consisting of proteins such as glue, gelatin, casein, and albumin.
  • water-soluble polymers include one or more selected from the group consisting of water-soluble polymers such as polyvinyl alcohol resins, polyethylene glycol, polyacrylamide, polyvinylpyrrolidone, polyacrylic acid, polyethyleneimine, anionic or cationic modified products thereof, hydrophobic modified products thereof, poly(meth)acrylic acid, polyvinylpyrrolidone, polyvinylamine, poly(maleic anhydride), polystyrene sulfonic acid, copolymers of (meth)acrylic acid or maleic anhydride with vinyl monomers (e.g., (meth)acrylic acid esters, aromatic vinyl monomers (styrene, etc.), olefin monomers, etc.), modified polyesters (modified with succinic anhydride, maleic anhydride, polyethylene oxide, etc.), and polyoxyethylene polymers.
  • water-soluble polymers such as polyvinyl alcohol resins, polyethylene glycol, polyacrylamide, polyvinylpyrrolidon
  • the polyvinyl alcohol resin may be, for example, a partially saponified grade polyvinyl alcohol resin.
  • the saponification degree of the polyvinyl alcohol resin is not particularly limited. For example, it can be 67 mol% or more, preferably 70 mol% or more, and for example, it can be 80 mol% or less, preferably 75 mol% or less. If the saponification degree is outside the above range, the dispersion stability may decrease, which may increase the number of aggregated particles or reduce the circularity.
  • the amount of water-soluble polymer added is not particularly limited. It can be, for example, 0.05 parts by mass or more, preferably 0.1 parts by mass or more, and for example, 5 parts by mass or less, preferably 3 parts by mass or less, per 100 parts by mass of water.
  • Dispersion medium examples include one or more selected from the group consisting of water, alcoholic solvents (methanol, ethanol, propanol, hexanol, ethylene glycol, diethylene glycol, 3- C1 - C5 alkoxy-3-methyl-1-butanol, 3- C1 - C5 alkoxy-3-methyl-1-butyl acetate, etc.), aliphatic hydrocarbon solvents (butane, pentane, hexane, cyclohexane, heptane, decane, hexadecane, etc.), aromatic hydrocarbon solvents (benzene, toluene, xylene, etc.), ester solvents (ethyl acetate, butyl acetate, etc.), ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), ether solvents (ethylene glycol dimethyl ether
  • a dispersion stabilizer can be used in the step of obtaining a polyhydroxyalkanoate resin suspension in Production Method I.
  • the dispersion stabilizer is not particularly limited as long as it functions as a dispersion stabilizer when the polyhydroxyalkanoate resin is emulsified and dispersed by heating and stirring in the presence of a dispersion medium, for example, by heating and stirring at a temperature of 110°C or higher and 180°C or lower.
  • examples of the dispersion stabilizer include poorly water-soluble inorganic compound particles whose surfaces may be treated with a surface treatment agent such as a silane coupling agent.
  • Slightly water-soluble inorganic compounds are substances with a solubility in water of less than 2.0 g/L, preferably less than 1.0 g/L, more preferably less than 100 mg/L, and even more preferably less than 50 mg/L.
  • Examples include one or more compounds selected from the group consisting of calcium carbonate, barium carbonate, magnesium carbonate, silica, alumina, titanium oxide, calcium sulfate, barium sulfate, magnesium sulfate, tricalcium phosphate (tricalcium phosphate), magnesium phosphate, aluminum phosphate, zinc phosphate, calcium pyrophosphate, magnesium pyrophosphate, aluminum pyrophosphate, zinc pyrophosphate, calcium metasilicate, etc.
  • phosphates and/or carbonates particularly tricalcium phosphate and/or calcium carbonate, are preferred because they are easy to remove after use.
  • the surface treatment agent used to treat the surface of poorly water-soluble inorganic compounds is not particularly limited as long as it is capable of imparting hydrophobicity.
  • examples include one or more selected from the group consisting of oils such as hydrocarbon oils, ester oils, and lanolin; silicones such as dimethylpolysiloxane, methylhydrogenpolysiloxane, and methylphenylpolysiloxane; fluorine compounds such as perfluoroalkyl group-containing esters, perfluoroalkylsilanes, perfluoropolyethers, and polymers having perfluoroalkyl groups; silane coupling agents such as 3-methacryloxypropyltrimethoxysilane and 3-glycidoxypropyltrimethoxysilane; titanium coupling agents such as isopropyl triisostearoyl titanate and isopropyl tris(dioctylpyrophosphate) titanate; metal soaps; fatty acids; amino acids such as
  • the amount of dispersion medium used in the emulsification/dispersion step can be, for example, 100 parts by mass or more, and can be, for example, 2000 parts by mass or less, preferably 1500 parts by mass or less, and more preferably 1000 parts by mass or less, per 100 parts by mass of polyhydroxyalkanoate resin particles, from the standpoints of sufficient stirring and mixing and productivity.
  • the amount of dispersion stabilizer used in the emulsification/dispersion step can be, from the standpoints of sufficient stirring and mixing and productivity, for example, 5 parts by mass or more, preferably 10 parts by mass or more, and can be, for example, 50 parts by mass or less, preferably 40 parts by mass or less, and more preferably 35 parts by mass or less, per 100 parts by mass of polyhydroxyalkanoate resin particles.
  • various surfactants can also be used in combination with the dispersion stabilizer, which is a poorly water-soluble inorganic compound.
  • the amount of surfactant added can be, for example, 0.01 parts by mass or more, and for example, 0.5 parts by mass or less, per 100 parts by mass of water.
  • Dispersion stabilizer removal means In the production method I for producing polyhydroxyalkanoate resin particles, when a dispersion stabilizer is used, it is preferable to remove the dispersion stabilizer (poorly water-soluble inorganic compound) before the step of separating the polyhydroxyalkanoate resin particles from the suspension.
  • the means for removing the dispersion stabilizer include adding a reagent that decomposes and dissolves the dispersion stabilizer, filtering off the dispersion stabilizer, etc. In the present invention, it is preferable to remove the dispersion stabilizer by adding a reagent that decomposes and dissolves the dispersion stabilizer.
  • the reagent for decomposing and dissolving the dispersion stabilizer from the viewpoint of inhibiting hydrolysis of the polyhydroxyalkanoate resin and preventing a decrease in spreadability on the skin when added to a topical preparation, it is preferable to add, for example, 1.05 to 1.50 times, more preferably 1.05 to 1.20 times the required number of moles of acid (hydrochloric acid, sulfuric acid, nitric acid, etc.), stir the mixture at 40°C or less, and filter and wash within 24 hours, more preferably within 12 hours.
  • 1.05 to 1.50 times more preferably 1.05 to 1.20 times the required number of moles of acid (hydrochloric acid, sulfuric acid, nitric acid, etc.
  • a method for separating the polyhydroxyalkanoate-based resin particles includes a dispersion medium removal treatment, which can be performed using, for example, a centrifugal dehydrator or a pressure dehydrator.
  • a dispersion medium may be added to the polyhydroxyalkanoate resin suspension to remove the solvent.
  • the dispersion medium may be added again and the solvent removal process may be carried out one or more times to wash the polyhydroxyalkanoate resin particles.
  • the amount of dispersion medium added, the number of washing and dispersion medium removal water treatment steps, the dehydration conditions, and the like are not particularly limited in the separation means and can be set appropriately.
  • the drying means used in the step of drying the separated polyhydroxyalkanoate resin particles is not particularly limited.
  • a drying means using a dryer can be used.
  • the dryer is not particularly limited, but examples include ovens, vacuum dryers, freeze dryers, reduced pressure dryers, stationary shelf dryers, mobile shelf dryers, fluidized bed dryers, rotary dryers, agitator dryers, and spray dryers.
  • freeze dryers, tray-type vacuum dryers, and vacuum dryers equipped with agitator blades are preferred, and an appropriate drying device can be selected depending on the particle size, resin type, and the like.
  • the drying conditions in the present invention are appropriately adjusted depending on the capacity, performance, etc. of the dryer used.
  • the degree of vacuum (relative to atmospheric pressure) can be set to ⁇ 0.001 MPa to ⁇ 0.1 MPa
  • the drying temperature can be set to 40° C. to 95° C.
  • the drying time can be set to 4 hours to 30 hours (hr).
  • the dried polyhydroxyalkanoate resin particles are preferably cooled and then classified as needed.
  • the method for cooling the polyhydroxyalkanoate resin particles after drying is not particularly limited.
  • the particles can be slowly cooled from the heating temperature during drying to a desired cooling temperature (for example, 40°C or lower, preferably room temperature (25°C ⁇ 5°C)) at an arbitrary cooling rate (for example, 0.5°C/min to 5°C/min). Cooling is preferably performed while stirring.
  • the method for classifying the dried polyhydroxyalkanoate resin particles is not particularly limited. Examples include air classification, airflow classification, screen classification, etc.
  • the classification is preferably carried out in an air atmosphere with a relative humidity of 30% or less, preferably 20% or less, so that the polyhydroxyalkanoate resin particles do not absorb moisture from the air.
  • the polyhydroxyalkanoate resin particles thus obtained are preferably stored as a packaged article sealed in a moisture-resistant packaging material so as not to absorb moisture in the air.
  • the topical preparation of the present invention is a topical preparation containing the biodegradable resin particles of the present invention.
  • topical preparations include cosmetics and quasi-drugs.
  • topical preparations include makeup cosmetics such as face powders, face powders (loose powder, pressed powder, etc.), foundations (powder foundation, liquid foundation, emulsion foundation, etc.), lipstick, lip balm, blush, eyebrow cosmetics, and nail polish; cleansing cosmetics such as soap, body shampoo, facial cleanser, scrub cleanser, and toothpaste; lotions such as pre-shave lotion and body lotion, topical body preparations such as body powder and baby powder, skin care cosmetics such as lotions, creams, and emulsions (makeup emulsions); sunscreen cosmetics, tanning products, antiperspirants (liquid antiperspirants, solid antiperspirants, cream antiperspirants, etc.), facial masks, hair washing cosmetics, hair dyes, hair styling products, aromatic cosmetics, bath additives, and shaving cream.
  • the topical preparation of the present invention can be one or more of these.
  • skin care cosmetics, cleansing cosmetics, sunscreen cosmetics, etc. are preferred, particularly from the viewpoint of reducing the environmental load, and powder foundations, emulsions, liquid foundations, scrub cleansers, etc. are more preferred.
  • the topical preparation of the present invention can be formulated with commonly used main ingredients or additives depending on the purpose, as long as the effects of the present invention are not impaired.
  • main ingredients or additives include one or more selected from the group consisting of water, alcohols with six or fewer carbon atoms (lower alcohols), oils and waxes, hydrocarbons, higher fatty acids, alcohols with seven or more carbon atoms (higher alcohols), sterols, fatty acid esters, metal soaps, humectants, surfactants, polymeric compounds, colorant raw materials, fragrances, clay minerals, preservatives/bactericides, anti-inflammatory agents, antioxidants, UV absorbers, organic-inorganic composite particles, pH adjusters (such as triethanolamine), specially formulated additives, and active pharmaceutical ingredients.
  • the curable resin among the binder resins is not particularly limited, as long as it is a resin that can be cured through a crosslinking reaction by heat or active energy rays (ultraviolet rays, electron beams, etc.) and has film-forming ability.
  • resins that can be cured by heat or active energy rays include resins with carbon-carbon unsaturated bonds. Examples include one or more of: polyfunctional (meth)acrylate resins such as polyhydric alcohol polyfunctional (meth)acrylate; polyfunctional urethane (meth)acrylate resins synthesized from polyisocyanates, polyols, and hydroxy group-containing (meth)acrylic acid esters; and epoxy (meth)acrylate resins.
  • polyhydric alcohol polyfunctional (meth)acrylate resins having three or more (meth)acryloyl groups per molecule include one or more of the following: trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, 1,2,4-cyclohexane tetra(meth)acrylate, pentaglycerol triacrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol triacrylate, dipentaerythritol pentaacrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol triacrylate, and tripentaerythritol hexaacrylate.
  • a polymerization initiator can be used in combination.
  • the polymerization initiator is not particularly limited as long as it can generate active species and initiate curing of the curable resin by heating or irradiation with active energy rays.
  • polymerization initiator examples include one or more of acetophenones, benzoins, benzophenones, phosphine oxides, ketals, ⁇ -hydroxyalkylphenones, ⁇ -aminoalkylphenones, anthraquinones, thioxanthones, azo compounds, peroxides, 2,3-dialkyldione compounds, disulfide compounds, fluoroamine compounds, aromatic sulfonium compounds, onium salts, borate salts, active halogen compounds, and ⁇ -acyloxime esters.
  • the solvent is not particularly limited as long as it can dissolve or disperse the binder resin or the curable resin.
  • the solvent include one or more of hydrocarbon solvents such as toluene and xylene; ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; ester solvents such as ethyl acetate and butyl acetate; and ether solvents such as dioxane, ethylene glycol diethyl ether and ethylene glycol monobutyl ether.
  • the solvent may be, for example, one or more of water and water-soluble organic solvents (alcohols, etc.).
  • the coating material of the present invention may optionally contain one or more of the following: surface conditioner, flowability conditioner, UV absorber, light stabilizer, curing catalyst, extender pigment, color pigment, metallic pigment, mica powder pigment, dye, etc.
  • the content of each component constituting the coating material of the present invention can be appropriately determined depending on the thickness of the coating film to be formed, the average particle size of the biodegradable resin particles, the coating method, and the like.
  • the content of the biodegradable resin particles in the coating material of the present invention can be, for example, from 1% by mass to 50% by mass, preferably from 3% by mass to 50% by mass, more preferably from 3% by mass to 45% by mass, and even more preferably from 5% by mass to 40% by mass, where the total content of the binder resin solids and the biodegradable resin particles is taken as 100% by mass.
  • the content of the solvent in the coating material of the present invention can be, for example, 10% by mass or more and 80% by mass or less, preferably 20% by mass or more and 60% by mass or less, when the total amount of the coating material is taken as 100% by mass.
  • the material constituting the substrate to which the coating material of the present invention is applied is not particularly limited, and examples thereof include one or more of metal, glass, ceramic, wood, paper, plastic, and composite materials composed of one or more of these.
  • the coating material of the present invention can be used to coat transparent substrates such as polyester resins (polyethylene terephthalate, etc.), polycarbonate resins, and (meth)acrylic resins.
  • the method for forming a coating film using the coating material of the present invention is not particularly limited, and examples thereof include one or more of a spray method, a roll method, a brush coating method, a reverse roll coating method, a gravure coating method, a die coating method, and a comma coating method.
  • the coating material is applied to any coating surface to form a coating film, and then further coated to produce a coating film. This coating film is then dried, and if necessary, cured to form a cross-linked coating film.
  • the resin composition of the present invention is a resin composition containing the biodegradable resin particles according to the present invention.
  • the resin composition may contain a base resin in addition to the biodegradable resin particles of the present invention.
  • the base resin include biodegradable resins such as polylactic acid, polyglycolic acid, polybutylene succinate, polybutylene succinate adipate, polybutylene adipate terephthalate, poly(ethylene succinate terephthalate), poly(butylene succinate terephthalate), poly(butylene adipate terephthalate), poly( ⁇ -caprolactone), poly( ⁇ -propiolactone), polyamide 4, poly(3-hydroxybutyrate), poly(3-hydroxyvalerate), poly(3-hydroxycaproate), poly(3-hydroxyheptanoate), poly(3-hydroxyoctanoate), poly(3-hydroxybutyrate-3-hydroxyhexanoate), poly(3-hydroxybutyrate-3-hydroxyvalerate
  • the content of each component constituting the resin composition of the present invention can be determined appropriately depending on the shape of the molded article formed from the resin composition, the average particle size of the biodegradable resin particles, the molding method, and the like.
  • the content of the biodegradable resin particles in the resin composition of the present invention can be, for example, 0.1% by mass or more and 70% by mass or less, preferably 0.5% by mass or more and 50% by mass or less, and more preferably 1% by mass or more and 30% by mass or less, when the total content of the base resin and the biodegradable resin particles is 100% by mass.
  • the resin composition of the present invention may be produced by any method, including mixing the base resin and biodegradable resin particles using a mechanical grinding and mixing method.
  • mechanical grinding and mixing methods include a Henschel mixer, V-type mixer, Turbula mixer, hybridizer, rocking mixer, or other mixing device, which mixes the base resin and biodegradable resin particles with stirring.
  • the resin composition of the present invention can be used as a molding material for obtaining a molded article.
  • the molding method for the molded article is not particularly limited.
  • the pellets can be molded by a molding method such as extrusion molding, injection molding, or blow molding.
  • Examples of molded articles obtained by molding the resin composition of the present invention include automotive materials, building materials, and packaging materials.
  • Example 2 A 2-L autoclave equipped with a stirring blade and a thermometer was charged with 620 parts by mass of ion-exchanged water, 60 parts by mass of a nonionic surfactant (polyethylene oxide polypropylene oxide copolymer; molecular weight approximately 10,000), and 5 parts by mass of polyvinyl alcohol (saponification degree: 72.9 mol%, viscosity of a 4 wt% aqueous solution at 20°C: 7.3 mPa s), and the mixture was stirred at 200 rpm for 2 hours.
  • a nonionic surfactant polyethylene oxide polypropylene oxide copolymer; molecular weight approximately 10,000
  • the obtained resin particles had a volume average primary particle diameter of 5.1 ⁇ m, a CV value of 34.5%, a contact angle of 91°, a circularity of 0.98, a BET specific surface area of 0.90 m 2 /g, and a melting point of 170°C. No residual crotonic acid, residual 2-pentenoic acid, or residual 4-pentenoic acid was detected, and it was confirmed that the total residual amount of unsaturated fatty acids was 10 ppm by mass or less.
  • Example 8 A 2-L autoclave equipped with a stirring blade and a thermometer was charged with 604 parts by mass of ion-exchanged water, 60 parts by mass of a nonionic surfactant (polyethylene oxide-polypropylene oxide copolymer; molecular weight approximately 8,000), and 20 g of polyethylene glycol (NOF Corporation's "PEG-20000”) and stirred at 200 rpm for 2 hours.
  • a nonionic surfactant polyethylene oxide-polypropylene oxide copolymer; molecular weight approximately 8,000
  • NOF Corporation's "PEG-20000” polyethylene glycol
  • Comparative Example 2 A powder foundation as an external preparation according to Comparative Example 2 was prepared in the same manner as in Example 9, except that the biodegradable resin particles obtained in Comparative Example 1 were used instead of the biodegradable resin particles obtained in Example 1.
  • Example 9 to 16 and Comparative Example 2 were evaluated by 10 panelists in terms of the feel when used (spreadability on the skin, compatibility with the skin, and cosmetic staying power) to test and evaluate the properties of the topical preparations. For the evaluation, each panelist gave 5 points (very good), 4 points (good), 3 points (fairly good), 2 points (not very good), or 1 point (not good) for each of the items of spreadability on the skin, skin compatibility, and cosmetic longevity, and the average score was used to evaluate the topical preparation characteristics test. Any item receiving less than 3.0 points was deemed to have failed. The results of the test evaluation of the properties of the topical preparation are shown in Table 1.
  • the powder foundation used as an external preparation containing the biodegradable resin particles of the present invention spreads easily on the skin, blends well with the skin, and provides excellent makeup wear.

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Abstract

Le problème abordé consiste à fournir des particules de résine biodégradable présentant une haute hydrophobicité, une excellente aptitude à l'étalement sur la peau et une excellente compatibilité avec la peau, une préparation topique contenant les particules de résine, une matière de revêtement contenant les particules de résine, une composition de résine contenant les particules de résine et un agent anti-bloquant contenant les particules de résine. L'invention concerne des particules de résine biodégradable contenant une résine de polyhydroxyalcanoate qui présentent une taille de particule primaire moyenne en volume de 3 µm à 50 µm, un angle de contact égal ou supérieur à 70°, une circularité de 0,90 à 1,00 et une surface spécifique BET de 0,1 m2/g à 10 m2/g ; une préparation topique contenant les particules de résine ; une matière de revêtement contenant les particules de résine ; une composition de résine contenant les particules de résine ; et un agent anti-bloquant contenant les particules de résine.
PCT/JP2025/001723 2024-02-09 2025-01-21 Particules de résine biodégradable et leur utilisation Pending WO2025169711A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018172578A (ja) * 2017-03-31 2018-11-08 日揮触媒化成株式会社 有機無機複合粒子、及び化粧料
JP2022022947A (ja) * 2020-06-30 2022-02-07 富士フイルムビジネスイノベーション株式会社 生分解性樹脂粒子
JP2022161001A (ja) * 2021-04-07 2022-10-20 松本油脂製薬株式会社 樹脂粒子及びその製造方法
JP2023184047A (ja) * 2022-06-17 2023-12-28 株式会社ダイセル 生分解性球状粒子及びその製造方法
JP2024054843A (ja) * 2022-10-05 2024-04-17 松本油脂製薬株式会社 樹脂粒子及びその用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018172578A (ja) * 2017-03-31 2018-11-08 日揮触媒化成株式会社 有機無機複合粒子、及び化粧料
JP2022022947A (ja) * 2020-06-30 2022-02-07 富士フイルムビジネスイノベーション株式会社 生分解性樹脂粒子
JP2022161001A (ja) * 2021-04-07 2022-10-20 松本油脂製薬株式会社 樹脂粒子及びその製造方法
JP2023184047A (ja) * 2022-06-17 2023-12-28 株式会社ダイセル 生分解性球状粒子及びその製造方法
JP2024054843A (ja) * 2022-10-05 2024-04-17 松本油脂製薬株式会社 樹脂粒子及びその用途

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