WO2024095351A1 - 多糖類含有粒子の製造方法、前駆体多糖類含有粒子及び多糖類含有粒子 - Google Patents

多糖類含有粒子の製造方法、前駆体多糖類含有粒子及び多糖類含有粒子 Download PDF

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Publication number
WO2024095351A1
WO2024095351A1 PCT/JP2022/040829 JP2022040829W WO2024095351A1 WO 2024095351 A1 WO2024095351 A1 WO 2024095351A1 JP 2022040829 W JP2022040829 W JP 2022040829W WO 2024095351 A1 WO2024095351 A1 WO 2024095351A1
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Prior art keywords
polysaccharide
particles
containing particles
salt
precursor
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PCT/JP2022/040829
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English (en)
French (fr)
Japanese (ja)
Inventor
綾太 小島
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Soken Kagaku KK
Soken Chemical and Engineering Co Ltd
Original Assignee
Soken Kagaku KK
Soken Chemical and Engineering Co Ltd
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Priority to PCT/JP2022/040829 priority Critical patent/WO2024095351A1/ja
Priority to PCT/JP2023/039305 priority patent/WO2024096016A1/ja
Priority to JP2024554530A priority patent/JPWO2024096016A1/ja
Priority to EP23885770.0A priority patent/EP4613797A4/en
Priority to CN202380071419.3A priority patent/CN120035623A/zh
Publication of WO2024095351A1 publication Critical patent/WO2024095351A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216Solid or semisolid forms
    • A61K8/022Powders; Compacted Powders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/736Chitin; Chitosan; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/00272-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/12Powdering or granulating
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/12Powdering or granulating
    • C08J3/122Pulverisation by spraying
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/12Powdering or granulating
    • C08J3/14Powdering or granulating by precipitation from solutions
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/08Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Definitions

  • the present invention relates to a method for producing polysaccharide-containing particles, precursor polysaccharide-containing particles, and polysaccharide-containing particles.
  • Patent Document 1 discloses a method for producing fine particles, which comprises spray-drying an aqueous solution in which a water-soluble polysaccharide and a reactive resin or a water-soluble crosslinking agent are dissolved to form granules, and heat-treating the resulting particles to crosslink and make them insoluble in water.
  • Patent Document 2 discloses a method for producing polysaccharide-containing particles, which comprises a spray-drying step in which a solution containing a polysaccharide and a polyhydric alcohol is spray-dried to obtain a precursor, and a heat-treatment step in which the precursor obtained in the spray-drying step is heated to obtain polysaccharide-containing particles.
  • the present invention was made in consideration of these circumstances, and provides a method for producing polysaccharide-containing particles using a desalting agent.
  • the present invention provides a method for producing polysaccharide-containing particles, the method comprising a spray-drying step and a heat-treating step, in which a dispersion containing polysaccharides in a salt state is spray-dried to obtain precursor polysaccharide-containing particles in the spray-drying step, and the heat-treating step involves heating the precursor polysaccharide-containing particles while contacting the polysaccharides in a salt state with a desalting agent, thereby desalting the polysaccharides in a salt state with the desalting agent to obtain polysaccharide-containing particles.
  • a method for producing polysaccharide-containing particles comprising a spray-drying step and a heat-treatment step, in which in the spray-drying step, a dispersion containing polysaccharides in a salt state is spray-dried to obtain precursor polysaccharide-containing particles, and in which in the heat-treatment step, the precursor polysaccharide-containing particles are heated while being brought into contact with the polysaccharides in a salt state and the polysaccharides in a salt state are desalted with the desalting agent to obtain polysaccharide-containing particles.
  • a precursor polysaccharide-containing particle comprising a polysaccharide in a salt state and a desalting agent capable of desalting the polysaccharide in a salt state.
  • a polysaccharide-containing particle comprising a polysaccharide and a neutralizing agent, the neutralizing agent being capable of neutralizing an acid or base capable of forming a salt with the polysaccharide.
  • the polysaccharide-containing particle according to [9] wherein the solubility of the polysaccharide-containing particle when immersed in water at 25°C for 7 days is 50 mass% or less.
  • the method for producing polysaccharide-containing particles according to the present invention uses a desalting agent to heat-treat salt-state polysaccharides to desalt them, thereby obtaining polysaccharide-containing particles that are poorly soluble in water and have little coloring. Furthermore, by taking advantage of their properties, the obtained polysaccharide-containing particles can be used in a variety of applications, such as topical cosmetic agents, paint additives, pharmaceutical additives, resin composition additives, film additives for imparting optical or anti-blocking properties, and process components for baking, polishing, etc., and can be used particularly for cosmetics.
  • the method for producing polysaccharide-containing particles according to the present invention includes a spray-drying step and a heat-treating step.
  • a spray-drying step a dispersion containing a polysaccharide in a salt state is spray-dried to obtain precursor polysaccharide-containing particles
  • the precursor polysaccharide-containing particles are heated in a state in which the polysaccharide in a salt state is brought into contact with a desalting agent, and the polysaccharide in a salt state is desalted with the desalting agent to obtain polysaccharide-containing particles.
  • the polysaccharide in a salt state is heated in a state in which the polysaccharide is in contact with the desalting agent.
  • the desalting agent may be added in any step as long as the polysaccharide in a salt state is in contact with the desalting agent in the heat treatment step.
  • the desalting agent can be added, for example, in the dispersion preparation step, in which a dispersion containing the polysaccharide in a salt state and the desalting agent is prepared and the dispersion is spray-dried to obtain precursor polysaccharide-containing particles containing the polysaccharide in a salt state and the desalting agent.
  • the desalting agent can also be added after the precursor polysaccharide-containing particles are obtained, for example, in the spray drying step.
  • the obtained precursor polysaccharide-containing particles can be immersed in a solution containing the desalting agent, sprayed and/or coated with a solution containing the desalting agent, or exposed to a gas containing the desalting agent, thereby adding the desalting agent and forming a state in which the desalting agent is in contact with the polysaccharide in a salt state.
  • the method for producing polysaccharide-containing particles may include a dispersion preparation step.
  • a dispersion preparation step a dispersion containing a polysaccharide in a salt state is prepared.
  • the dispersion contains the polysaccharide in a salt state, and may further contain a desalting agent when a desalting agent is added in the dispersion preparation step.
  • the dispersion may also contain inorganic particles.
  • the solvent for the dispersion liquid may be water, an organic solvent, or a mixed solvent of water and an organic solvent. Of these, it is preferable that the solvent contains water, and water is preferable.
  • water include natural water, purified water, distilled water, ion-exchanged water, pure water, etc., and of these, ion-exchanged water is preferable.
  • organic solvents include aliphatic monohydric alcohols such as methanol, ethanol, and isopropyl alcohol, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, and aromatic compounds such as toluene and xylene, and may be, for example, a mixed solvent of water and an organic solvent.
  • the dispersion contains a polysaccharide in a salt state.
  • the dispersion may be obtained by adding a polysaccharide in a salt state, i.e., a polysaccharide salt, to a solvent, or by adding a polysaccharide and a salt-forming agent to a solvent.
  • the polysaccharide in a salt state may be one type of compound.
  • the polysaccharide in a salt state may contain two or more types of compounds.
  • Polysaccharides include glucosamine-based and glucose unit-containing molecules.
  • Glucosamine-based polysaccharides include chitosan, which is ⁇ -1,4-glucosamine. Chitin, which is ⁇ -1,4-N-acetylglucosamine, is also included.
  • Molecules including glucose units include ⁇ -glucan.
  • ⁇ -glucan includes ⁇ -1,4-glucan and ⁇ -1,3-glucan.
  • ⁇ -1,4-glucan includes cellulose, cellulose acetate, ethyl cellulose, methyl cellulose, carboxymethyl cellulose, carboxyethyl cellulose, hydroxyethyl cellulose, and hydroxypropyl methyl cellulose.
  • ⁇ -1,3-glucan includes curdlan and paramylon.
  • Alginic acid which is a block polymer of ⁇ -D-mannuronic acid and ⁇ -L-guluronic acid, can also be included. Furthermore, derivatives of these can also be included.
  • the polysaccharide is preferably at least one selected from the group consisting of chitosan, cellulose, and their derivatives.
  • the polysaccharide salts include the above-mentioned polysaccharide salts, and the salt formers include acids or bases that can form a salt state of the polysaccharide used.
  • an acid can be used as the salt former.
  • the acid include organic acids such as carboxylic acids, and inorganic acids such as hydrochloric acid and sulfuric acid.
  • the carboxylic acids include the carboxylic acids listed as desalting agents described below.
  • a base can be used as the salt former.
  • the base include nitrogen-containing compounds and inorganic bases such as aluminum hydroxide and potassium hydroxide. Examples of the nitrogen-containing compounds include the nitrogen-containing compounds listed as desalting agents described below.
  • the polysaccharide in the salt state is preferably soluble in water.
  • the polysaccharide in the salt state can be more soluble than the desalted polysaccharide contained in the polysaccharide-containing particles described below.
  • the polysaccharide in the salt state can have a solubility of 80% by mass or more when immersed in water at 25°C for 7 days.
  • the polysaccharide in the salt state can have a solubility of, for example, 80, 85, 90, 95, 96, 97, 98, 99, or 100% by mass when immersed in water at 25°C for 7 days, and may be within a range between any two of the numerical values exemplified here.
  • the dispersion may contain a desalting agent.
  • the desalting agent is not particularly limited as long as it is a compound that neutralizes an acid or base that is a salt forming agent that forms a salt with a polysaccharide to desalt.
  • the desalting agent may include a compound that does not have a desalting function under a room temperature and atmospheric pressure environment, and that exhibits a desalting function by applying energy such as heat or light.
  • the desalting agent may be a base or an acid.
  • Examples of desalting agents that exhibit a desalting function by applying energy such as heat or light include a photo (thermal) base generator and a photo (thermal) acid generator, and an example of such a desalting agent is a curing agent for an epoxy resin.
  • the desalting agent may be a base when the salt forming agent is an acid, and may be an acid when the salt forming agent is a base.
  • the desalting agent may be a nitrogen-containing compound or a carboxylic acid. It is more preferable that the desalting agent has heat resistance that remains in the polysaccharide-containing particles obtained after the heat treatment step described below.
  • the nitrogen-containing compound may be at least one selected from the group consisting of carbamide, amine, acid amide, and nitrogen-containing heterocyclic compound.
  • carbamide include urea and urea derivatives. Specific examples include urea, methyl urea, ethyl urea, propyl urea, butyl urea, isobutyl urea, 1,1-dimethyl urea, 1,3-dimethyl urea, 1,1-diethyl urea, 1,3-diethyl urea, tetramethyl urea, 1,1,3,3-tetraethyl urea, and 1,1,3,3-tetrabutyl urea.
  • urea and tetramethyl urea are particularly preferred from the viewpoint of desalting effect.
  • the amine include compounds having an amine structure, such as alkylamines such as methylamine, ethylamine, n-propylamine, n-butylamine, n-amylamine, and n-hexylamine, alkanolamines such as methanolamine, triethanolamine, diethanolamine, monoethanolamine, propanolamine, isopropanolamine, and diisopropanolamine, and polyamines such as ethylenediamine, putrescine, cadaverine, hexamethylenediamine, and polyethylenediamine.
  • alkylamines such as methylamine, ethylamine, n-propylamine, n-butylamine, n-amylamine, and n-hexylamine
  • alkanolamines such as methanolamine, triethanolamine, diethanolamine,
  • the acid amide examples include compounds having a structure in which ammonia or a primary or secondary amine is dehydrated and condensed with an oxo acid, such as niacinamide, acetanilide, acetic acid amide, ⁇ -caprolactam, and ⁇ -butyrolactam.
  • nitrogen-containing heterocyclic compounds examples include pyridine, niacin, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2-hydroxy-4-methylpyridine, 2-hydroxy-6-methylpyridine, 2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine; pyrrolidines such as 1-methylpyrrolidine, 1-ethylpyrrolidine, 1-(2-hydroxyethyl)pyrrolidine, and 2-(2-hydroxyethyl)-1-methylpyrrolidine; piperidines such as 1-methylpiperidine, 1-ethylpiperidine, 1-(2-hydroxyethyl)piperidine, 1-(hydroxymethyl)piperidine, 3-hydroxy-1-methylpiperidine, 4-hydroxy-1-methylpiperidine, and 1,4-dimethylpiperidine; piperazines such as 1-methylpiperazine and 1-ethylpiperazine; natural extracts containing nitrogen-containing heterocycles; and nucleic acids such as purine bases and pyrimidine bases. From the viewpoint of the desalting effect, niacin,
  • Carboxylic acids include saturated fatty acids such as formic acid, acetic acid, propionic acid, and butyric acid; hydroxy acids such as lactic acid, malic acid, and citric acid; and dicarboxylic acids such as oxalic acid, succinic acid, and adipic acid.
  • the dispersion may contain inorganic particles.
  • inorganic particles include titanium oxide, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite, synthetic mica, phlogopite, lepidolite, biotite, lithia mica, silicic acid, anhydrous silicic acid, aluminum silicate, magnesium silicate, aluminum magnesium silicate, calcium silicate, barium silicate, strontium silicate, tungstate metal salt, hydroxyapatite, vermiculite, higilite, bentonite, montmorillonite, hectorite, zeolite, secondary calcium phosphate, alumina, aluminum hydroxide, boron nitride, boron nitride, and silica.
  • the inorganic particles are preferably plate-like
  • the average particle size of the inorganic particles can be 5 to 100 ⁇ m, for example, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100 ⁇ m, or between any two of the numerical values exemplified here.
  • the average particle size can be the volume average diameter measured by the laser diffraction scattering method.
  • the aspect ratio of the inorganic particles can be 20 to 200, for example, 20, 40, 60, 80, 100, 120, 140, 160, 180, 200, or between any two of the numerical values exemplified here.
  • the aspect ratio can be the long diameter/thickness of the inorganic particles.
  • the dispersion can contain 0.05 to 35% by mass of polysaccharide in a salt state.
  • concentration of the polysaccharide salt in the dispersion can be, for example, 0.05, 0.1, 0.5, 1, 5, 0, 5, 10, 15, 20, 25, 30, or 35% by mass, and can be within a range between any two of the numerical values exemplified here.
  • 1 to 300 parts by mass of the salt former can be added relative to 100 parts by mass of the polysaccharide.
  • the content of the salt former relative to 100 parts by mass of the polysaccharide can be, for example, 0, 50, 100, 150, 200, 250, or 300 parts by mass, and can be within a range between any two of the numerical values exemplified here.
  • the dispersion may contain 0.1 to 10.0 mass% of the desalting agent.
  • concentration of the desalting agent in the dispersion may be, for example, 0.1, 0.2, 0.3, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5, or 10.0 mass%, or may be within a range between any two of the numerical values exemplified here. It is preferable that the dispersion contains 1 part by mass or more of the desalting agent per 100 parts by mass of the polysaccharide in a salt state.
  • the content of the desalting agent per 100 parts by mass of the polysaccharide in a salt state in the dispersion may be, for example, 1, 2, 3, 5, 10, 15, 20, 25, or 30 parts by mass, or may be within a range between any two of the numerical values exemplified here.
  • the desalting agent plays a role in promoting the desalting of the salt-state polysaccharide in the heat treatment step described below, and it is preferable that the desalting agent remain in the polysaccharide-containing particles as a neutralizing agent thereafter. Therefore, it is preferable to add the desalting agent in excess so that it remains after the heat treatment step.
  • the concentration of the inorganic particles in the dispersion can be 0.1 to 70% by mass.
  • the concentration of the inorganic particles can be, for example, 0.1, 0.5, 1, 5, 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, or 70% by mass, and may be within a range between any two of the numerical values exemplified here. It is preferable that the dispersion contains 10 parts by mass or more of a salt-state polysaccharide per 100 parts by mass of inorganic particles.
  • the content of the salt-state polysaccharide relative to 100 parts by mass of inorganic particles in the dispersion is, for example, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 110, 120, 130, 140, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, 1200 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the structure and physical properties of the obtained polysaccharide-containing particles can be adjusted. For example, by sufficiently increasing the concentration of the salt-state polysaccharide in the dispersion and sufficiently increasing the content of the salt-state polysaccharide relative to the inorganic particles, it is possible to obtain polysaccharide-containing particles that include inorganic particles sufficiently coated with a coating layer containing polysaccharide.
  • the inorganic particles are plate-like or scaly particles such as mica
  • polysaccharide-containing particles that are composite particles in which a sufficient number and size of polysaccharide-containing spherical particles are attached to the surface of the inorganic particles or coating layer.
  • Inorganic particles sufficiently coated with a coating layer, or composite particles in which a sufficient number and size of polysaccharide-containing spherical particles are attached to the surface of the inorganic particles or coating layer can form powders with a low average friction coefficient and a high soft focus coefficient.
  • the dispersion may contain known components to the extent that the effects of the present invention are not impaired.
  • Known components include components that may be contained in the precursor polysaccharide-containing particles described below.
  • the viscosity of the dispersion is preferably 1 Pa ⁇ s or less. By adjusting the viscosity in this manner, polysaccharide-containing particles having an appropriate shape and/or structure can be obtained.
  • a treatment to adjust the viscosity and rheological properties of the dispersion may be carried out as necessary.
  • a treatment to reduce the viscosity, particularly the dynamic viscosity at high shear, or a treatment to impart pseudoplasticity or thixotropy can be mentioned.
  • these treatments can be carried out by adding a dispersant or by reducing the molecular weight of the organic material.
  • the dispersion can be prepared by stirring with a known stirrer, such as a disperser mixer, homomixer, or high-pressure homogenizer.
  • a stirrer such as a disperser mixer, homomixer, or high-pressure homogenizer.
  • the order of mixing in the dispersion preparation process is not particularly limited.
  • the polysaccharide salt (or the polysaccharide and the salt-forming agent) may be added to and mixed with the solvent, and the dispersion containing the polysaccharide in a salt state may be prepared first, and then the desalting agent may be added.
  • the mixing in this order precipitation of the polysaccharide can be prevented.
  • a dispersion containing a polysaccharide in a salt state is spray dried to obtain precursor polysaccharide-containing particles.
  • the precursor polysaccharide-containing particles according to the present invention contain a polysaccharide in a salt state, and may contain a desalting agent capable of desalting the polysaccharide in a salt state, and may further contain inorganic particles.
  • the dispersion liquid is supplied to a spray dryer adjusted to a predetermined temperature, and the dispersion liquid is sprayed to obtain precursor polysaccharide-containing particles.
  • the spray dryer is not particularly limited as long as it is a spray dryer used in the production of ordinary granules.
  • the spray dryer is - A raw material tank for storing the dispersion liquid; A raw material supply pump for supplying the dispersion liquid; - A nozzle (four-fluid nozzle, two-fluid nozzle, or one-fluid nozzle) or a rotating disk that turns the dispersion liquid into fine droplets, A drying chamber for drying and granulating the droplets; Blowers, filters, heaters for blowing dried and heated air or inert gas into the drying chamber; - Collectors that collect composite powder precursors using a two-point collection method, a cyclone method, a bag filter method, etc. (These may be heatable collectors) etc. may be provided.
  • the droplet formation conditions and drying conditions in the spray drying step By adjusting the droplet formation conditions and drying conditions in the spray drying step, the shape, structure and physical properties of the resulting precursor polysaccharide-containing particles can be adjusted.
  • the outlet temperature of the spray dryer can be 70 to 250°C.
  • the outlet temperature can be, for example, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, or 250°C, and may be within a range between any two of the values exemplified here.
  • a desalting agent is included in the dispersion, in the spray drying process, a portion of the salt-state polysaccharide in the resulting precursor polysaccharide-containing particles may be desalted by the desalting agent.
  • the spray drying process can also serve as a heat treatment process, which will be described later, by, for example, adjusting the drying conditions after granulation, or providing the spray dryer with a heating function or a heating chamber that can be heated and maintained for a certain period of time.
  • the precursor polysaccharide-containing particles are heated in a state where the polysaccharide in a salt state is brought into contact with a desalting agent, and the polysaccharide in a salt state is desalted with the desalting agent to obtain polysaccharide-containing particles.
  • the polysaccharide in a salt state is heated in a state where it is in contact with a desalting agent in the heat treatment process, the polysaccharide in a salt state is desalted with the desalting agent, and the crystallinity of the polysaccharide is increased, thereby improving water resistance (reducing solubility).
  • the desalting and/or improvement in crystallinity of the polysaccharide in a salt state is promoted by performing heat treatment in the presence of a desalting agent, and a strong and robust state in which the polysaccharide molecules are more densely hydrogen-bonded to each other can be easily created, thereby improving water resistance.
  • yellowing of the material can be prevented by performing heating in the presence of a desalting agent.
  • the water resistance can be improved by heating at a lower temperature and/or for a shorter time, thereby preventing yellowing of the material.
  • the desalting agent can be added in any step in the heat treatment step, it can be added after the precursor polysaccharide-containing particles are obtained in the spray drying step.
  • the manufacturing method according to one embodiment of the present invention can include a desalting agent addition step before and/or during the heat treatment step.
  • the obtained precursor polysaccharide-containing particles are immersed in a solution containing a desalting agent, sprayed and/or coated with a solution containing a desalting agent, or exposed to a gas containing a desalting agent, thereby adding a desalting agent and forming a state in which the desalting agent is in contact with the salt-state polysaccharide.
  • the desalting agent include the desalting agents listed in the dispersion preparation step.
  • the solution can contain 0.1 to 10.0 mass % of the desalting agent.
  • the concentration of the desalting agent in the solution is, for example, 0.1, 0.2, 0.3, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5, 10.0% by mass, and may be within any two of the numerical values exemplified here.
  • the amount of the desalting agent added is preferably 1 part by mass or more per 100 parts by mass of the salt-state polysaccharide contained in the precursor polysaccharide-containing particle.
  • the content of the desalting agent per 100 parts by mass of the salt-state polysaccharide contained in the precursor polysaccharide-containing particle is, for example, 1, 2, 3, 5, 10, 15, 20, 25, 30 parts by mass, and may be within any two of the numerical values exemplified here.
  • the heat treatment is preferably performed at 100° C. or higher and lower than 200° C.
  • the heat treatment temperature may be, for example, 100, 105, 110, 115, 120, 125, 130, 135, 140, 145, 150, 155, 160, 165, 170, 175, 180, 185, 190, 195 ° C., or less than 200 ° C., or may be within a range between any two of the values exemplified here.
  • the heat treatment time may be, for example, 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, or 300 minutes, or may be within a range between any two of the values exemplified here.
  • the heat treatment can be carried out under the following condition A.
  • the heating temperature of condition A can be 100°C or more and less than 150°C, for example, 100, 105, 110, 115, 120, 125, 130, 135, 140, 145°C, less than 150°C, and may be within a range between any two of the numerical values exemplified here.
  • the heating time of condition A can be 20 minutes or more, for example, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300 minutes, and may be within a range between any two of the numerical values exemplified here.
  • the heat treatment can be performed under the following condition B. B 150° C. or more and less than 200° C., 1 minute or more and less than 90 minutes
  • the heating temperature of condition B can be 150° C.
  • the heating time of condition B can be 1 minute or more and less than 90 minutes, for example, 1, 2, 3, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85 minutes, less than 90 minutes, and may be within a range between any two of the numerical values exemplified here.
  • the heat treatment conditions are preferably a temperature and time such that the color difference ⁇ E of the solid content when the obtained polysaccharide-containing particles are immersed in water is 0 to 60, and preferably a temperature and time such that the color difference ⁇ E of the solid content when the obtained polysaccharide-containing particles are immersed in water is, for example, 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, or 60, and is within a range between any two of the numerical values exemplified here.
  • the precursor polysaccharide-containing particle and the polysaccharide-containing particle according to the present invention will be described below.
  • the precursor polysaccharide-containing particles can be obtained by spray-drying a dispersion containing the polysaccharide in a salt state (and a desalting agent, if necessary) in the above-mentioned spray-drying step.
  • the precursor polysaccharide-containing particles according to the present invention contain a polysaccharide in a salt state.
  • the precursor polysaccharide-containing particles according to one embodiment of the present invention contain a polysaccharide in a salt state and a desalting agent capable of desalting the polysaccharide in a salt state.
  • a part of the polysaccharide in a salt state in the precursor polysaccharide-containing particles may be desalted by the desalting agent, that is, the precursor polysaccharide-containing particles may contain desalted polysaccharide.
  • polysaccharide in a salt state examples include the polysaccharide in a salt state, the desalting agent, and the polysaccharide listed in the explanation of the dispersion liquid preparation step of the method for producing polysaccharide-containing particles.
  • the precursor polysaccharide-containing particles contain a desalting agent
  • the content of the desalting agent per 100 parts by mass of the polysaccharide in a salt state in the dispersion liquid is, for example, 0.1, 0.2, 0.3, 0.5, 1, 2, 3, 5, 10, 15, 20, 25, or 30 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the precursor polysaccharide-containing particles can be spherical particles.
  • Spherical particles include nearly spherical particles and are intended to mean particles with a rounded shape.
  • the maximum diameter/minimum diameter of the spherical particles is preferably 0.5 to 1.5, and more preferably 0.8 to 1.2.
  • the spherical particles can also include partially crushed or cut spherical shapes such as hemispherical (lens-like, etc.) particles, but it is preferable that at least half of the particles have a maximum diameter/minimum diameter in the above numerical range.
  • the spherical particles can also have few dents or wrinkles on the surface and can be smooth.
  • the average particle size of the spherical particles can be 10 ⁇ m or less.
  • the average particle size can be 0.1 to 10 ⁇ m, for example, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 ⁇ m, and may be within a range between any two of the numerical values exemplified here.
  • the average particle size of the spherical particles can be measured by SEM observation.
  • the average particle size can be calculated by measuring the particle size of each spherical particle and averaging the results.
  • the precursor polysaccharide-containing particles may further contain inorganic particles.
  • inorganic particles include the inorganic particles listed in the explanation of the dispersion liquid preparation step of the method for producing polysaccharide-containing particles.
  • the precursor polysaccharide-containing particles contain inorganic particles (e.g., mica), it is preferable that the precursor polysaccharide-containing particles contain a total of 10 parts by mass or more of salt-state polysaccharides and polysaccharides per 100 parts by mass of inorganic particles.
  • inorganic particles e.g., mica
  • the total content of the polysaccharides in a salt state and the polysaccharides relative to 100 parts by mass of inorganic particles in the dispersion liquid is, for example, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 110, 120, 130, 140, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, or 1200 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the precursor polysaccharide-containing particle when the precursor polysaccharide-containing particle includes an inorganic particle, the precursor polysaccharide-containing particle can be a composite particle including an inorganic particle, a coating layer, and a spherical particle.
  • the coating layer can be one that covers the inorganic particle.
  • the spherical particle can be attached to the inorganic particle or the coating layer that covers the inorganic particle.
  • the coating layer and the spherical particle can include a polysaccharide in a salt state, and can include a desalting agent capable of desalting the polysaccharide in a salt state, or can include desalted polysaccharide.
  • the structure and physical properties of the resulting polysaccharide-containing particles can be adjusted by adjusting the type and amount of inorganic particles and salt-state polysaccharides and polysaccharides in the precursor polysaccharide-containing particles. For example, by sufficiently increasing the concentration of salt-state polysaccharides and polysaccharides in the precursor polysaccharide-containing particles and sufficiently increasing the content of salt-state polysaccharides and polysaccharides relative to the inorganic particles, precursor polysaccharide-containing particles containing inorganic particles sufficiently coated with a coating layer containing salt-state polysaccharides and polysaccharides can be obtained.
  • precursor polysaccharide-containing particles polysaccharide-containing particles that can constitute a powder with a high soft focus coefficient can be obtained.
  • the inorganic particles are plate-like particles or scale-like particles such as mica
  • precursor polysaccharide-containing particles that are composite particles in which a sufficient number and size of precursor polysaccharide-containing spherical particles are attached to the surface of the inorganic particles or the coating layer can be obtained.
  • polysaccharide-containing particles polysaccharide-containing particles that can constitute a powder with a low average friction coefficient and a high soft focus coefficient can be obtained.
  • the precursor polysaccharide-containing particles include inorganic particles
  • the coating layer includes polysaccharides in a salt state, and may include a desalting agent capable of desalting the polysaccharides in a salt state, or may include desalted polysaccharides.
  • the fact that the inorganic particles are covered with a coating layer can be confirmed by SEM observation, EDS (energy dispersive X-ray analysis), re-dissolving the coating layer that covers the inorganic particles and confirming its mass, etc.
  • polysaccharide-containing particles including inorganic particles covered with a coating layer containing polysaccharides can be obtained through a heat treatment process.
  • Such polysaccharide-containing particles can constitute a powder with excellent soft focus properties because the inorganic particles are covered with a coating layer.
  • the precursor polysaccharide-containing particle contains an inorganic particle
  • at least one spherical particle may be attached to the inorganic particle and/or coating layer in the precursor polysaccharide-containing particle.
  • the inorganic particle is a plate-like or scaly particle such as mica
  • particles attached to inorganic particles refer to particles attached to inorganic particles directly or via a coating layer.
  • the number of spherical particles attached to one inorganic particle may be, for example, 1, 2, 3, 5, 9, 10, 15, 20, 15, 30, 31, 40, 50, 60, 70, 80, 90, or 100, and may be within a range between any two of the numerical values exemplified here.
  • the presence or absence of spherical particles attached to inorganic particles and the number of spherical particles attached to one inorganic particle can be confirmed by observing the polysaccharide-containing particle with a SEM.
  • some of the spherical particles may not be attached to inorganic particles, and the precursor polysaccharide-containing particles containing inorganic particles according to one embodiment of the present invention may also contain spherical particles that are not attached to inorganic particles.
  • the precursor polysaccharide-containing particles according to one embodiment of the present invention may contain a total of 50 parts by mass or more of the polysaccharide in a salt state, the polysaccharide, the salt-forming agent (and inorganic particles, if necessary) per 100 parts by mass of the precursor polysaccharide-containing particles, for example, 50, 60, 70, 80, 90, or 100 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the precursor polysaccharide-containing particles according to one embodiment of the present invention may also be composed of the polysaccharide in a salt state, the polysaccharide, the salt-forming agent (and inorganic particles, if necessary).
  • the precursor polysaccharide-containing particles according to one embodiment of the present invention may contain known components used in polysaccharide-containing particles, for example, known components used in cosmetics, within the scope of not impairing the effects of the present invention.
  • known components include organic powders, oily components, surfactants, UV absorbers, moisturizers, anti-fading agents, antioxidants, defoamers, preservatives, fragrances, solubilizers, plasticizers, viscosity adjusters, skin beautifying components (skin whitening agents, cell activators, skin roughness improving agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.), vitamins, amino acids, antiperspirants, alcohol, film-forming agents, anti-inflammatory agents, cooling agents, nucleic acids, hormones, inclusion compounds, pH adjusters, chelating agents, etc.
  • Polysaccharide-containing particles can be obtained by heating precursor polysaccharide-containing particles in a state where a desalting agent is in contact with the polysaccharide in a salt state, and desalting the polysaccharide in a salt state with the desalting agent.
  • the polysaccharide-containing particles according to the present invention include a polysaccharide and a neutralizing agent.
  • the neutralizing agent is capable of neutralizing an acid or base capable of forming a salt with the polysaccharide.
  • the neutralizing agent can be a desalting agent that is contained in the precursor polysaccharide-containing particles and remains in the polysaccharide-containing particles even after the heat treatment process.
  • the polysaccharide-containing particles may contain polysaccharides in a salt state that were not desalted in the heat treatment process, but from the viewpoint of improving water resistance, it is preferable that the content of polysaccharides in a salt state is low.
  • the content of polysaccharides in a salt state can be confirmed by the evaluation of solubility described later.
  • the polysaccharide-containing particles may not contain polysaccharides in a salt state.
  • Examples of polysaccharides and polysaccharides in a salt state include the polysaccharides and polysaccharides in a salt state listed in the explanation of the dispersion liquid preparation step of the method for producing polysaccharide-containing particles.
  • Examples of the neutralizing agent include the desalting agents listed in the explanation of the dispersion liquid preparation step in the method for producing polysaccharide-containing particles.
  • the solubility of the desalted polysaccharide when immersed in water at 25°C for 7 days is less than 80% by mass.
  • the solubility of the desalted polysaccharide when immersed in water at 25°C for 7 days is, for example, 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75% by mass, less than 80% by mass, and may be within a range between any two of the numerical values exemplified here.
  • the polysaccharide-containing particles preferably contain 0.01 parts by mass or more of a desalting agent per 100 parts by mass of the polysaccharides and salt-state polysaccharides in the polysaccharide-containing particles combined.
  • the content of the desalting agent per 100 parts by mass of the salt-state polysaccharides in the dispersion may be, for example, 0.01, 0.02, 0.03, 0.05, 0.1, 0.2, 0.3, 0.5, 1, 2, 3, 5, 10, 15, 20, 25, or 30 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the polysaccharide-containing particles can be obtained by heating precursor polysaccharide-containing particles and desalting the salt-state polysaccharides with a desalting agent, and the shape and average particle size can be the same as those of the precursor polysaccharide-containing particles.
  • the polysaccharide-containing particles may further contain inorganic particles.
  • inorganic particles include the inorganic particles listed in the explanation of the dispersion liquid preparation step of the method for producing polysaccharide-containing particles.
  • the polysaccharide-containing particles include inorganic particles (e.g., mica), it is preferable that the polysaccharide-containing particles contain a total of 10 parts by mass or more of polysaccharide and polysaccharide in a salt state per 100 parts by mass of the inorganic particles.
  • inorganic particles e.g., mica
  • the total content of polysaccharides and salt-state polysaccharides relative to 100 parts by mass of inorganic particles in the dispersion liquid is, for example, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 110, 120, 130, 140, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, or 1200 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the polysaccharide-containing particle can be a composite particle including an inorganic particle, a coating layer, and a spherical particle.
  • the coating layer can be one that covers the inorganic particle.
  • the spherical particle can be attached to the inorganic particle or the coating layer that covers the inorganic particle.
  • the coating layer and the spherical particle can include a neutralizing agent that can neutralize the polysaccharide and an acid or base that can form a salt with the polysaccharide, and can include the polysaccharide in a salt state.
  • the structure and physical properties of the polysaccharide-containing particles can be adjusted by adjusting the type and amount of inorganic particles, and polysaccharides and polysaccharides in a salt state in the polysaccharide-containing particles. For example, by sufficiently increasing the concentration of polysaccharides and polysaccharides in a salt state in the polysaccharide-containing particles and sufficiently increasing the content of polysaccharides and polysaccharides in a salt state relative to the inorganic particles, the polysaccharide-containing particles can be made to include inorganic particles sufficiently coated with a coating layer containing polysaccharides and polysaccharides in a salt state.
  • the polysaccharide-containing particles can form a powder with a high soft focus coefficient.
  • the polysaccharide-containing particles are composite particles in which a sufficient number and size of polysaccharide-containing spherical particles are attached to the surface of the inorganic particles or the coating layer.
  • the polysaccharide-containing particles can form a powder with a low average friction coefficient and a high soft focus coefficient.
  • the polysaccharide-containing particles include inorganic particles
  • the coating layer contains polysaccharides and a neutralizing agent capable of neutralizing acids or bases capable of forming salts with the polysaccharides, and may contain polysaccharides in a salt state. That the inorganic particles are coated with a coating layer can be confirmed by SEM observation, EDS (energy dispersive X-ray analysis), separating precursor polysaccharide-containing particles, redissolving the coating layer that coats the inorganic particles, and confirming its mass, etc.
  • the polysaccharide-containing particles according to the present invention can constitute a powder with excellent soft focus properties because the inorganic particles are coated with a coating layer.
  • the polysaccharide-containing particle contains an inorganic particle
  • at least one spherical particle may be attached to the inorganic particle and/or coating layer in the polysaccharide-containing particle.
  • the inorganic particle is a plate-like or scaly particle such as mica
  • particles attached to inorganic particles refer to particles attached to inorganic particles directly or via a coating layer.
  • the number of spherical particles attached to one inorganic particle may be, for example, 1, 2, 3, 5, 9, 10, 15, 20, 15, 30, 31, 40, 50, 60, 70, 80, 90, or 100, and may be within a range between any two of the numerical values exemplified here.
  • the presence or absence of spherical particles attached to inorganic particles and the number of spherical particles attached to one inorganic particle can be confirmed by observing the polysaccharide-containing particle with a SEM.
  • some of the spherical particles may not be attached to inorganic particles, and the polysaccharide-containing particles containing inorganic particles according to one embodiment of the present invention may also contain spherical particles that are not attached to inorganic particles.
  • the polysaccharide-containing particles according to one embodiment of the present invention may contain a total of 50 parts by mass or more of polysaccharide, polysaccharide in a salt state, and neutralizing agent (and inorganic particles, if necessary) per 100 parts by mass of the polysaccharide-containing particles, for example, 50, 60, 70, 80, 90, or 100 parts by mass, and may be within a range between any two of the numerical values exemplified here.
  • the polysaccharide-containing particles according to one embodiment of the present invention may also be composed of polysaccharide, polysaccharide in a salt state, and neutralizing agent (and inorganic particles, if necessary).
  • the polysaccharide-containing particles according to one embodiment of the present invention may contain known components used in polysaccharide-containing particles, for example, known components used in cosmetics, to the extent that the effect of the present invention is not impaired.
  • known components include those listed as known components that may be contained in precursor polysaccharide-containing particles.
  • the polysaccharide-containing particles according to one embodiment of the present invention have a solubility of 50% by mass or less, more preferably 30% by mass or less, when immersed in water at 25° C. for 7 days.
  • the solubility may be 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50% by mass, and may be within a range between any two of the values exemplified here.
  • solubility (mass%)] (A - B) / A x 100
  • solubility of the polysaccharide-containing particles can be controlled by adjusting the type and amount of polysaccharide, as well as the production conditions during production of the polysaccharide-containing particles (the type and amount of salt-state polysaccharide and desalting agent to be blended in the dispersion, as well as the heating treatment temperature and time).
  • the solubility of the residue (components containing polysaccharide and neutralizing agent) remaining after removing the inorganic particles from the polysaccharide-containing particles is within the above range.
  • polysaccharide-containing particles it is preferable that gelation and swelling are not observed when 1 g of the polysaccharide-containing particles is immersed in 10 times the amount of ion-exchanged water at 25°C for 7 days.
  • the polysaccharide-containing particles it is preferable that the polysaccharide-containing particles have a lower solubility than the precursor polysaccharide-containing particles before the heat treatment process.
  • the difference between the solubility of the polysaccharide-containing particles when immersed in water at 25°C for 7 days and the solubility of the precursor polysaccharide-containing particles when immersed in water at 25°C for 7 days is, for example, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95% by mass, and may be within a range between any two of the numerical values exemplified here.
  • the polysaccharide-containing particles according to one embodiment of the present invention preferably have a color difference ⁇ E of 0 to 60 when the polysaccharide-containing particles are immersed in water.
  • ⁇ E can be a value relative to a reference white color in the L*a*b* color space.
  • the color difference ⁇ E can be, for example, 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, or 60, and may be within a range between any two of the numerical values exemplified here.
  • the color difference ⁇ E of the solid content of the polysaccharide-containing particles when immersed in water can be controlled by adjusting the type and amount of polysaccharide, as well as the manufacturing conditions during the manufacture of the polysaccharide-containing particles (the type and amount of the polysaccharide in the salt state and the desalting agent to be blended in the dispersion, and the heat treatment temperature and time), in particular the heat treatment temperature and time.
  • the polysaccharide-containing particles are preferably biodegradable.
  • Biodegradability means that the polymer decomposes and disappears in the earth's environment, such as in soil or seawater, and/or decomposes and disappears in the living body.
  • the polysaccharide-containing particles preferably have a BOD decomposition rate of 60% or more when exposed to activated sludge for 28 days based on OECD TG301C.
  • the polysaccharide-containing particles preferably have a relative decomposition rate of 60% or more with respect to cellulose when buried in soil based on JIS K 6955 (ISO17556).
  • the polysaccharide-containing particles preferably have a relative decomposition rate of 60% or more with respect to cellulose when placed in seawater and sandy sediments based on ISO19679.
  • the biodegradability of the residue (component containing polysaccharides and neutralizing agent) obtained by removing the inorganic particles from the polysaccharide-containing particles is as described above.
  • the polysaccharide-containing particles according to one embodiment of the present invention can have a soft focus factor (SFF) of 0.86 or more, and can be 0.86 to 1.40.
  • the soft focus factor can be, for example, 0.86, 0.90, 0.95, 1.00, 1.05, 1.10, 1.15, 1.20, 1.25, 1.3, 1.35, or 1.40, or can be within a range between any two of the values exemplified here.
  • the soft focus factor can be measured by applying the polysaccharide-containing particles to a skin material such as bioskin and using a goniophotometer.
  • the light source is fixed, and the sensor is scanned from 0° to 180° to measure the luminance at each angle, and the ratio of the luminance at the two points (luminance at 65°/luminance at 135°) can be taken as the soft focus factor.
  • the soft focus factor By setting the soft focus factor to the above lower limit or more, a cosmetic product with reduced glare can be obtained.
  • the soft focus coefficient By setting the soft focus coefficient at or above the lower limit, it is possible to produce a cosmetic product with brightness that takes advantage of the high brightness of the inorganic particles themselves, such as mica, which are the body pigment.
  • the soft focus coefficient can be adjusted by the type and structure of the components of the polysaccharide-containing particles. In particular, it can be adjusted by controlling the amount of the coating layer on the inorganic particles, such as mica, and the number and size of the spherical particles.
  • the polysaccharide-containing particles according to one embodiment of the present invention can have an average coefficient of friction (MIU) of 0.75 or less, and can be 0.40 to 0.75.
  • MIU average coefficient of friction
  • the average coefficient of friction can be, for example, 0.40, 0.45, 0.50, 0.55, 0.60, 0.65, 0.70, or 0.75, and can be within a range between any two of the numerical values exemplified here.
  • the average coefficient of friction can be determined by applying the polysaccharide-containing particles to a skin material such as bioskin and scanning it with a friction tester, and can be measured specifically by the method described in the Examples.
  • the cosmetic powder By having an average coefficient of friction equal to or greater than the above lower limit, the cosmetic powder can be maintained in a regular state after application to the skin, and a cosmetic product with excellent cosmetic retention can be obtained. In addition, there is little crumbling or falling off during or after molding by compression, etc., and the cosmetic product has excellent moldability. If the average coefficient of friction is equal to or less than the above upper limit, a cosmetic product that is smooth, does not feel squeaky, and can be applied evenly can be obtained.
  • the average coefficient of friction can be adjusted by the type and structure of the components of the polysaccharide-containing particles, and in particular by controlling the number and size of the spherical particles that adhere to the inorganic particles such as mica.
  • polysaccharide-containing particles are obtained that are poorly soluble in water and have little coloring by a mechanism of desalting a salt-state polysaccharide by heat treatment using a desalting agent.
  • polysaccharide-containing particles that do not contain a crosslinking agent or a crosslinked structure can be obtained.
  • polysaccharide-containing particles that are non-toxic to ecosystems, highly biodegradable, and reduce the amount of organic solvent used can be obtained, thereby meeting the needs of the industry to create more environmentally friendly products.
  • the polysaccharide-containing particles of the present invention have the above-mentioned properties, are poorly soluble in water, and are little colored.
  • the cosmetics may be in liquid, gel, or solid form, such as foundation, face powder, eye shadow, eye liner, eyebrow pencil, blush, lipstick, and nail polish.
  • the polysaccharide-containing particles including inorganic particles according to one embodiment of the present invention comprise inorganic particles sufficiently coated with a coating layer containing polysaccharides and polysaccharides in a salt state, and can further be composite particles in which a sufficient number and size of saccharide-containing spherical particles are attached to the surface of the inorganic particles or the coating layer.
  • the polysaccharide-containing particles can provide a powder with a low average coefficient of friction and a high soft focus coefficient, i.e., a cosmetic product with excellent slip properties and soft focus properties can be obtained.
  • Example 1 Dispersion liquid preparation step> Chitosan (KOYO CHITOSAN FL-80, manufactured by KOYO CHEMICAL CO., LTD.) and acetic acid were added to water and mixed. Urea was further added to the obtained aqueous solution to prepare a dispersion containing polysaccharides in a salt state, with a chitosan concentration of 5 mass%, an acetic acid concentration of 5 mass%, and urea of 0.5 mass%, and a desalting agent.
  • Chitosan KYO CHITOSAN FL-80, manufactured by KOYO CHEMICAL CO., LTD.
  • ⁇ Spray drying process> A two-fluid nozzle type laboratory spray dryer was used, the inlet temperature of the spray dryer was set to 200° C., and spray drying was performed to obtain precursor polysaccharide-containing particles 1 containing a desalting agent. When the inlet temperature of the spray dryer was set to 200° C., the outlet temperature was 70 to 120° C.
  • ⁇ Heat treatment step> The obtained precursor polysaccharide-containing particles 1 containing the desalting agent were heated at 120° C. for 240 minutes in an air atmosphere to obtain polysaccharide-containing particles 1.
  • Examples 2 to 18, Comparative Examples 1 to 7 The formulation of the dispersion and the conditions of the heat treatment were as shown in Tables 1 to 3, and polysaccharide-containing particles 2 to 18 were obtained.
  • Example 19 ⁇ Dispersion liquid preparation step> Mica (average particle size 20 ⁇ m), chitosan (KOYO CHITOSAN FL-80, manufactured by KOYO CHEMICAL CO., LTD.) and acetic acid were added to water and mixed. Urea was further added to the obtained aqueous solution to prepare a dispersion with a mica concentration of 5 mass%, a chitosan concentration of 5 mass%, an acetic acid concentration of 5 mass%, and urea of 0.5 mass%.
  • Natural mica average particle size 20 ⁇ m
  • Chitosan Koyo Chitosan FL-80, manufactured by Koyo Chemical Co., Ltd.
  • Polysaccharide-containing particles have precipitated in water, and no swelling of the particles is observed.
  • the obtained polysaccharide-containing particles 19 were applied to Bioskin (manufactured by Viewlax) at 10 mg/ cm2 , and the soft focus coefficient was evaluated using a goniophotometer (GC-5000L, manufactured by Nippon Denshoku Industries Co., Ltd.) Specifically, a light source was fixed at a position of 45°, and the Bioskin surface to which the composite powder was applied was scanned with a sensor from 0° to 180° to measure the luminance at each angle, and the ratio of the luminance at the two points (luminance at 65°/luminance at 135°) was taken as the soft focus coefficient.
  • GC-5000L manufactured by Nippon Denshoku Industries Co., Ltd.

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PCT/JP2022/040829 2022-10-31 2022-10-31 多糖類含有粒子の製造方法、前駆体多糖類含有粒子及び多糖類含有粒子 Ceased WO2024095351A1 (ja)

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PCT/JP2022/040829 WO2024095351A1 (ja) 2022-10-31 2022-10-31 多糖類含有粒子の製造方法、前駆体多糖類含有粒子及び多糖類含有粒子
PCT/JP2023/039305 WO2024096016A1 (ja) 2022-10-31 2023-10-31 多糖類含有粒子の製造方法、前駆体多糖類含有粒子及び多糖類含有粒子
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EP23885770.0A EP4613797A4 (en) 2022-10-31 2023-10-31 PROCESS FOR PRODUCING POLYSACCHARIDE PARTICLES, PRECURSOR POLYSACCHARIDE PARTICLES AND POLYSACCHARIDE PARTICLES
CN202380071419.3A CN120035623A (zh) 2022-10-31 2023-10-31 含多糖类的粒子的制造方法、含前体多糖类的粒子及含多糖类的粒子

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JPS63210101A (ja) * 1987-02-26 1988-08-31 Fuji Boseki Kk キトサン又はキチン多孔質超微小粒状体の製造方法
JPS6466204A (en) * 1987-09-07 1989-03-13 Fuji Spinning Co Ltd Fine colored granule of chitosan
JPH08239311A (ja) * 1995-03-03 1996-09-17 Sekisui Plastics Co Ltd 保湿性複合粒子およびその製造方法
JP2017186489A (ja) * 2016-03-31 2017-10-12 藤倉化成株式会社 キトサン含有着色塗料、キトサン含有着色ゲル粒子および塗料組成物
JP2022046073A (ja) * 2020-09-10 2022-03-23 積水化成品工業株式会社 多糖類粒子、化粧料、及び、多糖類粒子の製造方法
JP2022094097A (ja) * 2020-12-14 2022-06-24 積水化成品工業株式会社 多糖類含有粒子の製造方法
JP2022135891A (ja) * 2021-03-05 2022-09-15 積水化成品工業株式会社 多糖類含有粒子、該粒子の製造方法、及び該粒子の用途

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JPS63161001A (ja) * 1986-12-25 1988-07-04 Fuji Boseki Kk キチン又はキトサン微小着色粒状体
JP3267060B2 (ja) 1994-07-19 2002-03-18 日清紡績株式会社 微粒子の製造方法

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JPS63210101A (ja) * 1987-02-26 1988-08-31 Fuji Boseki Kk キトサン又はキチン多孔質超微小粒状体の製造方法
JPS6466204A (en) * 1987-09-07 1989-03-13 Fuji Spinning Co Ltd Fine colored granule of chitosan
JPH08239311A (ja) * 1995-03-03 1996-09-17 Sekisui Plastics Co Ltd 保湿性複合粒子およびその製造方法
JP2017186489A (ja) * 2016-03-31 2017-10-12 藤倉化成株式会社 キトサン含有着色塗料、キトサン含有着色ゲル粒子および塗料組成物
JP2022046073A (ja) * 2020-09-10 2022-03-23 積水化成品工業株式会社 多糖類粒子、化粧料、及び、多糖類粒子の製造方法
JP2022094097A (ja) * 2020-12-14 2022-06-24 積水化成品工業株式会社 多糖類含有粒子の製造方法
JP2022135891A (ja) * 2021-03-05 2022-09-15 積水化成品工業株式会社 多糖類含有粒子、該粒子の製造方法、及び該粒子の用途

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