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WO2025035956A1 - Particules janus à base de matériau naturel et leur procédé de préparation - Google Patents

Particules janus à base de matériau naturel et leur procédé de préparation Download PDF

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Publication number
WO2025035956A1
WO2025035956A1 PCT/CN2024/100540 CN2024100540W WO2025035956A1 WO 2025035956 A1 WO2025035956 A1 WO 2025035956A1 CN 2024100540 W CN2024100540 W CN 2024100540W WO 2025035956 A1 WO2025035956 A1 WO 2025035956A1
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Prior art keywords
particles
acid
natural material
functional substance
natural
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Chinese (zh)
Inventor
杨振忠
孙大吟
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Tsinghua University
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Tsinghua University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H99/00—Subject matter not provided for in other groups of this subclass, e.g. flours, kernels
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B02—CRUSHING, PULVERISING, OR DISINTEGRATING; PREPARATORY TREATMENT OF GRAIN FOR MILLING
    • B02C—CRUSHING, PULVERISING, OR DISINTEGRATING IN GENERAL; MILLING GRAIN
    • B02C1/00—Crushing or disintegrating by reciprocating members
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B02—CRUSHING, PULVERISING, OR DISINTEGRATING; PREPARATORY TREATMENT OF GRAIN FOR MILLING
    • B02C—CRUSHING, PULVERISING, OR DISINTEGRATING IN GENERAL; MILLING GRAIN
    • B02C19/00—Other disintegrating devices or methods
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/04—Compounds of zinc
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/04—Compounds of zinc
    • C09C1/043—Zinc oxide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3009—Physical treatment, e.g. grinding; treatment with ultrasonic vibrations
    • C09C1/3018—Grinding
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3063—Treatment with low-molecular organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/309—Combinations of treatments provided for in groups C09C1/3009 - C09C1/3081
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/40—Compounds of aluminium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/40—Compounds of aluminium
    • C09C1/405—Compounds of aluminium containing combined silica, e.g. mica
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/04—Physical treatment, e.g. grinding, treatment with ultrasonic vibrations
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/04—Physical treatment, e.g. grinding, treatment with ultrasonic vibrations
    • C09C3/041—Grinding
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
    • C09F1/04—Chemical modification, e.g. esterification
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer

Definitions

  • the invention relates to natural material-based Janus particles, belonging to the field of composite materials.
  • particles used in industrial applications are mostly round in shape. They are usually composed of the same substance, and their particle surface and internal composition are exactly the same.
  • the undifferentiated single structure can only be applied to simple usage scenarios, and will have difficulty in functioning for complex systems, especially multi-scale complex systems.
  • Janus particles usually refer to a particle with two different components or structures, and the two parts have clear partitions. This type of particle with significant anisotropy is different from traditional homogeneous particles and can play a unique role in emulsification, grinding, lubrication, and functional substance delivery. In addition, Janus particles are expected to be used as functional preparation carriers in more complex environments.
  • materials made of natural materials have been widely used in our production and life as main materials, industrial additives, decorative items, daily chemical products, functional materials, etc., and have played many functions such as cleaning, adsorption, beauty, health care, and treatment. Especially in the complex environment of the human body, they have played a positive role. Among them, pulverizing them into particles is the most prominent way of use.
  • the subject of the present invention is to provide a natural material-based Janus particle and a preparation method thereof.
  • a multi-stage preparation method can be used to achieve programmed multi-scale particle multi-stage preparation and its corresponding sequential modification, thereby obtaining natural material particles loaded with more functional substances, thereby completing the present invention.
  • the present invention solves the problem of the present invention through the following solutions.
  • a natural material-based Janus particle comprising a natural material-based particle, and functional substances A and B that are different from each other and modified on the surface of the natural material-based particle; wherein the average diameter of the natural material-based particle is 100 nm to 50 ⁇ m.
  • the natural material-based particles are particles composed of natural materials, wherein the content of natural materials is 80% by mass or more; the natural materials are one or more materials derived from organisms and natural inorganic substances, and the natural materials are preferably natural organic substances, more preferably polysaccharide macromolecular colloids, and further preferably selected from peach gum and gum.
  • the material derived from an organism is one or more of materials derived from plants or animals; the material derived from plants is preferably one or more of materials derived from roots, stems, leaves, seeds, and pollen of plants, and more preferably plant powder; the material derived from animals is one or more selected from cells, blood, milk or dairy products, bones, pearls, shells, and crustaceans, and preferably selected from shellac and pearl powder.
  • the particles according to [2], wherein the material derived from natural inorganic substances is one or more of clay and minerals, preferably selected from mica, silica, and zinc oxide.
  • the functional substance A and the functional substance B are independently selected from compounds having one or more functional groups of carboxyl, sulfonic acid, phosphoric acid, amino, imidazole, pyridine and their salts; the area ratio of the surface area modified by the functional substance A to the surface area modified by the functional substance B is (10-1):1.
  • steps (b) and (d) are carried out in a solvent
  • the solvent is preferably selected from one or more of water, alcohols, ketones, ethers, hydrocarbons, and sulfoxide solvents, and more preferably selected from one or more of water, methanol, ethanol, alcohol, propylene glycol, glycerol, panthenol, acetone, THF, DMSO, n-hexane, cyclohexane, isohexadecane, and C7-16 isoparaffin.
  • the natural material-based Janus particles of the present invention compound more functional substances with natural material particles and construct a Janus structure.
  • the natural material-based Janus particles of the present invention have multiple functions, and the prominent anisotropy in the structure can bring new rheological behaviors to the dispersed system and play more and more unique roles, such as cleaning, grinding, penetration, transdermal, protective, modifying, beautifying, and maintenance.
  • the word “may” means both performing a certain process and not performing a certain process.
  • references to “some specific/preferred embodiments”, “other specific/preferred embodiments”, “embodiments”, etc. mean that the specific elements (e.g., features, structures, properties and/or characteristics) described in connection with the embodiments are included in at least one embodiment described herein, and may or may not exist in other embodiments.
  • the elements may be combined in various embodiments in any suitable manner.
  • the numerical range expressed using "a numerical value A to a numerical value B" means a range including the endpoints numerical values A and B.
  • the temperature when “normal temperature” or “room temperature” is used, the temperature may be 10-40°C.
  • An object of the present invention is to provide a natural material-based Janus particle, which includes a natural material-based particle, and functional substances A and functional substances B that are different from each other and modified on the surface of the natural material-based particle; wherein the average diameter of the natural material-based particle is 100nm to 50 ⁇ m.
  • the surface of Janus particles has a surface area modified by functional substance A and a surface area modified by functional substance B, wherein in the surface area modified by functional substance A, the proportion of functional substance A in all surface-modified substances is 80% by mass or more, preferably 90% by mass or more; in the surface area modified by functional substance B, the proportion of functional substance B in all surface-modified substances is 80% by mass or more, preferably 90% by mass or more.
  • the area ratio of the surface area modified by the functional substance A to the surface area modified by the functional substance B is (10-1):1.
  • Functional substance A and functional substance B can be connected to the natural material-based particles through chemical bonds or physical interactions.
  • the physical interactions can be hydrogen bonds, van der Waals forces, electrostatic forces, etc.
  • the chemical bonds can be covalent bonds, ionic bonds, metallic bonds, etc.
  • Functional substance A and functional substance B are preferably connected through chemical bonds.
  • natural material means a material that comes from nature and has not been processed or has only been physically processed.
  • natural material-based particles refer to particles composed of natural materials, wherein the content of natural materials is 80 mass % or more, for example, 90 mass % or more, for example, 95 mass % or more, or 100%.
  • the natural material constituting the natural material-based particles which can be any suitable natural material.
  • the natural material particles used in the present invention are natural materials listed in the INCI cosmetic raw material list issued by the Cosmetics Department of the State Food and Drug Administration.
  • the natural material is one or more of materials derived from organisms and natural inorganic substances.
  • the natural material derived from organisms may be one or more materials derived from plants or animals.
  • the plant-derived material is one or more of the materials derived from the root, stem, leaf, seed, and pollen of the plant.
  • Examples thereof include, but are not limited to: Bonat Spirulina powder, Chinese medicinal material powder, grain powder, plant powder, plant root powder, plant leaf powder, tea, tea powder, brown sugar paste powder, barley powder, barley leaf powder, barley seed powder, light bamboo leaf powder, rice husk powder, rice powder, pollen, cordyceps mycelium powder, catechu gum, catechu leaf powder, catechu wood powder, Poria powder, Poria sclerotium powder, starch, cassava starch, modified potato starch, modified corn starch, rice powder, citrus peel powder, peel powder, Guangxi sand orange peel powder, pectin, seaweed seeds, plant seeds, fruit seeds, Candelilla wax, brown algae, walnut shell powder, amber powder, pollen, peanut powder, bark, bark powder, coffee powder, cocoa shell powder, gelatin, natto gum, peach gum
  • the animal-derived material is one or more of animal tissues, cells, blood, milk or dairy products, bones, pearls, shells, and carapaces.
  • animal tissues, cells, blood, milk or dairy products, bones, pearls, shells, and carapaces include, but are not limited to, conchiolin powder, milk powder, honey, bee pollen, propolis, propolis wax, bee pollen, beeswax, royal jelly, royal jelly powder, dried egg yolk, dried cheese, cicada molt, silk, hydrolyzed silk, quaternary ammonium salt-79 hydrolyzed silk, blood, red deer blood meal, milk, milk powder, yogurt powder, shellac, purple shellac, purple shellac wax, animal bones, bone meal, pearls, buffalo horns, antelope horns, earthworms, cochineal, pearls, pearl powder, mother-of-pearl, mother-of-pearl powder, mother-of-pearl oyster powder, etc.
  • the material derived from natural inorganic substances is one or more of clay and ore.
  • clay include, but are not limited to, Hokkaido Akan clay, kaolin, loess, activated clay, volcanic ash, volcanic mud, bentonite, quaternary ammonium salt-18 bentonite, Canadian bentonite, Manigogen glacial mud, montmorillonite,ixie lava clay, fuller's earth, Haiermu clay, etc.
  • the ore may be a metal ore, a metal oxide ore, etc., examples of which include but are not limited to gallstones, opal powder, tourmaline, calcite, zeolite, pumice, attapulgite, silica, diatomaceous earth, sea silt, talc, yellow ochre, volcanic sand, silica silylate, alum, potassium alum, gold, diamond powder, gold Real estate, malachite, sapphire powder, rhodochrosite, smithsonite, sulfur, sulfur powder, barium sulfate, calcium sulfate, calcium sulfate hydrate, silver sulfate, calamine, aluminum, aluminum powder, aluminum closa, silver chloride, bismuth oxychloride, medical stone, borax, hydroxyapatite, calcium hydroxide, aluminum hydroxide, chromium hydroxide green, quartz, calcium carbonate, zinc carbonate, iron powder, copper powder, zi
  • the natural material is a natural organic matter, more preferably a polysaccharide macromolecular colloid, and further preferably selected from peach gum and gum.
  • the natural material is plant powder.
  • the functional substance A and the functional substance B which may be any suitable substance that can modify the surface of natural material particles to impart specific functions thereto.
  • the functional substance A and the functional substance B are independently selected from compounds having one or more functional groups selected from carboxyl group, sulfonic acid group, phosphoric acid group, amino group, imidazole group, pyridyl group and salts thereof.
  • functional substance A and functional substance B are independently selected from carboxylic acids and their derivatives, amino acids and their derivatives, sulfonic acids and their derivatives, polyhydroxy compounds and their derivatives, phosphonic acids and their derivatives, organic amines and their derivatives, imidazoles, imidazolidinyl ureas, pyridine and its derivatives, organosilanes, etc.
  • the carboxylic acid may be selected from aliphatic carboxylic acids, alicyclic carboxylic acids, aromatic carboxylic acids, and heterocyclic carboxylic acids, wherein the aliphatic carboxylic acid may be a straight-chain or branched, saturated or unsaturated aliphatic carboxylic acid.
  • the sulfonic acid can be selected from aliphatic sulfonic acid, alicyclic sulfonic acid, aromatic sulfonic acid, and heterocyclic sulfonic acid.
  • the aliphatic sulfonic acid can be a linear or branched, saturated or unsaturated aliphatic sulfonic acid.
  • the phosphonic acid can be selected from aliphatic phosphonic acid, alicyclic phosphonic acid, aromatic phosphonic acid, and heterocyclic phosphonic acid.
  • the aliphatic phosphonic acid may be a linear or branched, saturated or unsaturated aliphatic phosphonic acid.
  • the derivatives of carboxylic acid, sulfonic acid, phosphonic acid or amino acid can be in the form of salt, ester, amide or the like of carboxylic acid, sulfonic acid, phosphonic acid or amino acid, respectively, or can be derivatives in which the part other than carboxyl, sulfonic acid group and phosphonic acid group is substituted by a substituent.
  • the salt can be an alkali metal salt (such as lithium, sodium, potassium, etc.) or an alkaline earth metal salt (such as calcium, magnesium, etc.).
  • the ester can be an ester obtained by reacting carboxylic acid, sulfonic acid, phosphonic acid or amino acid with a fatty alcohol, alicyclic alcohol or aromatic alcohol, wherein the alcohol can be a monohydric alcohol or a polyhydric alcohol, and can be saturated or unsaturated.
  • the amide can be obtained by reacting carboxylic acid, sulfonic acid, phosphonic acid or amino acid with an amine, and the amine can be a fatty amine or an aromatic amine, and can be a monoamine or a polyamine.
  • the substituent can be a hydroxyl, a sulfhydryl, a polymer segment optionally having a functional group, etc.
  • Polyols are organic compounds that have two or more hydroxyl groups in one molecule.
  • the organic amine may be an aliphatic amine, an alicyclic amine, an aromatic amine, or a heterocyclic amine.
  • the derivative of the organic amine may be a derivative in which an organic group other than an amino group is substituted by a substituent or a sulfate of the organic amine, etc.
  • the substituent may be a hydroxyl group, a segment having an oxyalkylene repeating unit, etc.
  • the derivatives of pyridine refer to derivatives in which the pyridine ring is substituted by a substituent, wherein the substituent includes but is not limited to carboxyl, amino, hydroxyl, and alkyl substituted by carboxyl, amino or hydroxyl.
  • functional substance A and functional substance B are independently selected from lauric acid, sodium laurate, tartaric acid, disodium tartrate, disodium 2-sulfolaurate, stearic acid, sodium stearate, tetrasodium pyrophosphate, 4-amino-3-hydroxybutyric acid, oleic acid, sodium oleate, phosphoric acid, sodium dihydrogen phosphate, trisodium phosphate, sodium benzenesulfonate, 3-aminopropanesulfonic acid, sodium ligninsulfonate, sodium C12-15 polyether-3 sulfate, sodium C12-15 polyether-7 carboxylate, sodium C12-15 polyether sulfate, sodium C12-15 alkyl sulfate, sodium C14-16 olefin sulfonate, 4-hydroxybenzoic acid, sodium C4-12 olefin/maleic acid copolymer , EDTA (salt), trisodium H
  • Another object of the present invention is to provide a method for preparing the natural material-based Janus particles of the present invention, which comprises the following steps:
  • substances A and B are modified intermittently and sequentially, and the intermittent and sequential modification process is performed alternately with the mechanical crushing process.
  • the natural material is ground into powder to form a coarse natural material with a particle size of 1 to 100 ⁇ m.
  • These particles are modified with composite substance A to obtain natural material particles with a primary larger particle size and the outer surface of which is modified with functional substance A.
  • the equipment parameters are changed, and the natural material is crushed into powder by mechanical crushing to form fine natural material with a particle size of 100 nm to 50 ⁇ m. Some areas on the surface of these particles are areas that have been modified with composite substance A before.
  • the particles are broken into smaller pieces, and fresh parts that have not been modified with substance A are exposed at the broken parts. These particles are further modified with composite substance B to obtain natural material particles with a smaller particle size and the outer surface of which is modified with functional substance B.
  • Functional substance A and functional substance B can be solid or liquid independently.
  • functional substance A and functional substance B are solid, and no solvent is used in the steps (b) and (d). That is, functional substance A and functional substance B are directly contacted with natural material particles in a solid state to modify the surface of the natural material particles.
  • the steps (b) and (d) are carried out in a solvent.
  • the solvent is preferably one or more selected from water, alcohols, ketones, ethers, hydrocarbons, and sulfoxide solvents.
  • the solvent is more preferably one or more selected from water, methanol, ethanol, alcohol, propylene glycol, glycerol, panthenol, acetone, THF, DMSO, n-hexane, cyclohexane, isohexadecane, and C7-16 isoparaffin.
  • the crushing in steps (a) and (c) is mechanical crushing, more preferably carried out in a mortar, a high-speed blender, a high-speed shearing machine, a ball mill, a high-speed air flow crushing, a high-pressure air flow crushing, a high-temperature and high-pressure disintegration, a water-jet crushing, an ultrafine grinder, an ultrafine pulverizer, a nano grinder, a nano pulverizer or a freezing crusher.
  • the ball mill used is a planetary ball mill, PM2L
  • the grinding conditions are 220V, 50Hz, 0.75KW
  • the API nano ball mill used is FRITSCH/Germany PULVERISETTE 7 enhanced type.
  • the ball mill was reset to gear 2 and the grinding was continued for 30 minutes to obtain fine particles with an average particle size of 500 nm. These fine particles were smaller in size than the coarse particles, except that part of the outer surface was modified by stearic acid, and further broken and fractured to expose fresh parts at the broken and fractured parts.
  • the natural material particles prepared by the above process in multiple stages have Janus structural characteristics, and thus are natural material-based Janus particles.
  • Embodiment 2 is a diagrammatic representation of Embodiment 1:
  • the ball mill was reset to gear 2 and the grinding was continued for 30 minutes to obtain fine particles with an average particle size of 1 ⁇ m. These fine particles were smaller in size than the coarse particles, except that part of the outer surface was modified by hyaluronic acid, and further broken and fractured to expose fresh parts at the broken and fractured parts.
  • Embodiment 3 is a diagrammatic representation of Embodiment 3
  • 100g of shellac was placed in a planetary ball mill, and the ball mill was set to gear 1, and the grinding was continued for 30 minutes. After the coarse grinding was completed, the above powder was dispersed in water, heated to 40°C and stirred at 60rpm/min. 1.0g of sodium stearate powder was added to the dispersion of the above powder, and the modification process lasted for 30 minutes. After filtering and drying, natural material particles with stearic acid modified on the outer surface of the particles were obtained, and the average particle size was 100 ⁇ m.
  • the ball mill was reset to gear 2 and the grinding was continued for 30 minutes to obtain fine particles with an average particle size of 50 ⁇ m. These fine particles were smaller in size than the coarse particles, except that part of the outer surface was modified by stearic acid, and further broken and fractured to expose fresh parts at the broken and fractured parts.
  • Embodiment 4 is a diagrammatic representation of Embodiment 4:
  • the API nano ball mill was reset to gear 2 and crushed for 10 minutes to obtain fine particles with an average particle size of 400 nm. These fine particles are smaller than the coarse particles, except that some areas of the outer surface are modified by stearic acid, and further crushing and breaking exposes fresh parts at the crushing and breaking sites.
  • Embodiment 5 is a diagrammatic representation of Embodiment 5:
  • the above granular powder was dispersed in water with a solid content of 50%. After 10 min of crushing, fine particles were obtained with an average particle size of 1 ⁇ m. These fine particles were smaller in size than the coarse particles, except that part of the outer surface was modified by histidine, and fresh parts were exposed at the crushing and breaking sites through further crushing and breaking.
  • the natural material-based Janus particles of the present invention can be widely used in the fields of cosmetics, industrial additives, medical treatment, etc.

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Abstract

La présente invention concerne des particules Janus à base de matériau naturel et leur procédé de préparation. Les particules Janus à base de matériau naturel de la présente invention comprennent des particules à base de matériau naturel, et des substances fonctionnelles A et des substances fonctionnelles B qui modifient les surfaces des particules à base de matériau naturel et sont différentes les unes des autres, le diamètre moyen des particules à base de matériau naturel étant de 100 nm à 50 µm. Selon la présente invention, un procédé de préparation à niveaux multiples est utilisé pour mettre en œuvre une préparation multi-niveaux programmée de particules à échelles multiples et une modification séquentielle correspondante, de façon à obtenir des particules à base de matériau naturel chargées avec davantage de substances fonctionnelles.
PCT/CN2024/100540 2023-08-17 2024-06-21 Particules janus à base de matériau naturel et leur procédé de préparation Pending WO2025035956A1 (fr)

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