[go: up one dir, main page]

US20040121019A1 - Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation - Google Patents

Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation Download PDF

Info

Publication number
US20040121019A1
US20040121019A1 US10/346,690 US34669003A US2004121019A1 US 20040121019 A1 US20040121019 A1 US 20040121019A1 US 34669003 A US34669003 A US 34669003A US 2004121019 A1 US2004121019 A1 US 2004121019A1
Authority
US
United States
Prior art keywords
particle
radiation
group
exposure
active principle
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/346,690
Other languages
English (en)
Inventor
Eric Perrier
Isabelle Bonnet
Charlotte De Matteis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Beauty Care Solutions France SAS
Original Assignee
Coletica SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Coletica SA filed Critical Coletica SA
Assigned to COLETICA reassignment COLETICA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BONNET, ISABELLE, DE MATTEIS, CHARLOTTE, PERRIER, ERIC
Publication of US20040121019A1 publication Critical patent/US20040121019A1/en
Assigned to ENGELHARD LYON SA reassignment ENGELHARD LYON SA CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: COLETICA SA
Assigned to BASF BEAUTY CARE SOLUTIONS FRANCE SAS reassignment BASF BEAUTY CARE SOLUTIONS FRANCE SAS CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: ENGELHARD LYON
Priority to US13/069,922 priority Critical patent/US8957001B2/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/14—Liposomes; Vesicles
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/606—Nucleosides; Nucleotides; Nucleic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/81—Preparation or application process involves irradiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0009—Galenical forms characterised by the drug release technique; Application systems commanded by energy involving or responsive to electricity, magnetism or acoustic waves; Galenical aspects of sonophoresis, iontophoresis, electroporation or electroosmosis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

Definitions

  • the invention relates mainly to a particle comprising at least one biopolymer which is degradable under the effect of an electromagnetic wave, notably the wavelength of which is in the spectrum of the wavelengths emitted by the sun, this biopolymer comprising nucleosides.
  • the invention finds cosmetic, dermatological, pharmaceutical, agri-food or agro-industrial use, in releasing an active principle contained by this particle when it is subjected to an electromagnetic wave.
  • pH-dependent polymers such as Eudragit® S and L (Bayer), cellulose acetate phthalate, cellulose acetate trimellitate and hydroxypropyl methyl cellulose phthalate has enabled the development of gastro-resistant microspheres which release a low amount of an active in an acid medium (0.1N HCl) but which have very rapid release kinetics after a sharp increase of the pH (towards 6-7) (Palmieri et al, 2002, J. Microencaps., 19, 1, 111-119; Lorenzo et al, 1997, J. Microencaps., 14, 5, 607-616).
  • microencapsulated active is not very much released in a gastric medium (which is very acidic), and this enables for example reducing the risks of irritation of the gastric mucosa, which phenomena are observed for many chemical compounds.
  • microspheres or microcapsules which release their actives under the action of light and/or ultra-violets (UV).
  • UV ultra-violets
  • the spheres or capsules thus obtained could in fact release anti-oxidants, solar filters or molecules enabling inducing a barrier effect, only when the skin really needs it, the encapsulation enabling avoiding the skin contact and penetration of certain actives which are particularly irritant, even allergenic (vitamin A, vitamin E, solar filters, perfumes, etc . . . ).
  • the doses of solar energy which are necessary for the degradation of the film are very significant (500,000 kJ/m 2 ), doses which correspond to more than 15 days of exposure in full Summer (Getajimann et al., 1994, Polym. Deg. Stab., 43, 343-352) and which are therefore incompatible with the rapid degradation expected during a daily solar exposure (as an indication, the daily solar energy received varies from 5,000 to 10,000 kJ/m 2 ).
  • Certain derivatives of N-isopropylacrylamide can also acquire a very interesting reactivity to ultra-violets by grafting of a UV-photosensitive molecule such as bis(4-dimethylamino)phenylmethyl leucocyanide (Mamada et al., 1990, Macromolecules, 23, 1517-1519).
  • a UV-photosensitive molecule such as bis(4-dimethylamino)phenylmethyl leucocyanide (Mamada et al., 1990, Macromolecules, 23, 1517-1519).
  • the ultra-violet light first of all creates an ionization reaction in the gel formed from this polymer, and this leads to an increase in the internal osmotic pressure and a swelling of the gel. In the absence of ultra-violet light, the equilibrium is reversed and the gel beaks up, it is said that the gel “collapses”.
  • the grafting of chromophores which are sensitive to light, such as, for example, the chlorophyllin-copper complex or its trisodium salts, onto N-isopropylacrylamide polymers enables obtaining gels which are reactive to visible light (Suzuki et al., 1990, Nature, 1990, 346, 26, 345-347; Qiu et al., 2001, Adv. Drug. Deliv. Rev., 53, 321-339).
  • the chromophore absorbs the solar energy to locally transform it into heat, in thus increasing the temperature of the gel.
  • the increase in the temperature thus leads to a contraction of the gel.
  • the use of these gels in microspheres could enable a release of the active at the moment at which the gel contracts.
  • Yui's group (Yui et al., 1993, J. Controlled Release, 26, 141-145) proposed the use of a gel of hyaluronic acid coupled to a photosensitizer, methylene blue, as support medium of the microspheres. Under the effect of the light, there is a production of OH o radicals which de-polymerize and fluidify the hyaluronic acid gel, and thus enable the degradation of the spheres and the release of the active principles.
  • a main aim of the invention is to solve the novel technical problem consisting of providing particles which are formed from natural biopolymers, which can deliver active principles which are optionally contained by these particles, under the action of an electromagnetic wave, notably the wavelength of which is in the spectrum of the wavelengths emitted by the sun.
  • Another aim of the invention is to solve the novel technical problem consisting of providing such particles which contain an active principle which is active in the field of cosmetics, dermatology, pharmacy, agri-food or agro-industry.
  • Another main aim of the invention is to solve the novel technical problem consisting of providing a cosmetic, dermatological, pharmaceutical, agri-food or agro-industrial composition, comprising at least one particle as defined above.
  • Another aim of the invention is to solve the technical problem consisting of providing a solution enabling releasing an active principle in relation with the exposure to an electromagnetic wave, notably the wavelength of which corresponds to that emitted by the sun.
  • the present invention describes a technique for obtaining particles which are formed from natural biopolymers which can deliver their actives (cosmetic, dermatological, pharmaceutical, agri-foods or agro-industrial actives) under the action of light, and this at doses which are more compatible with a moderate exposure of the order of a day, even a dose of a few hours for cosmetic applications for example.
  • microspheres or microcapsules, nanospheres and nanocapsules, liposomes which are described in the present invention, are made by the use of deoxyribonucleic acid (DNA), ribonucleic acid (RNA), of oligonucleotides or of oligonucleosides.
  • DNA deoxyribonucleic acid
  • RNA ribonucleic acid
  • oligonucleotides or of oligonucleosides are in fact classically known for their sensitivity to UV radiation, a sensitivity which can induce, in vivo, mutations of the genes carried by these structures within the chromosomes for example.
  • the free radicals formed (Hanson et al., 2002, Photochem. Photobiol., 76, 1, 57-63) ⁇ hydrolyze >> the DNA, RNA molecules, the oligonucleotides or the oligonucleosides which constitute the membrane of the sphere, of the capsule or of the liposome.
  • the free radicals for example on the skin, which progressively cause a local rupture of the membrane of the sphere, of the capsule or of the liposome, and thus enable releasing the active.
  • the invention relates to a particle comprising at least one biopolymer which is degradable under the effect of an electromagnetic wave, notably the wavelength of which is in the spectrum of the wavelengths emitted by the sun, this biopolymer comprising nucleosides.
  • the biopolymer is selected from the group consisting of a DNA, an RNA, an oligonucleotide, an oligonucleoside, or one of a mixture of these.
  • the biopolymer is selected from the group consisting of DNA of marine origin, RNA of marine origin, DNA of plant origin, RNA of plant origin, oligo-antisenses, polyamide nucleic acids (PNA), small interfering RNAs (siRNAs), messenger RNAs or mRNAs, hybrid molecules containing an oligonucleosidic and/or oligonucleotidic part, and oligonucleosides and oligonucleotides having chemical modifications such as graftings of hydrophobic molecules.
  • PNA polyamide nucleic acids
  • siRNAs small interfering RNAs
  • messenger RNAs or mRNAs hybrid molecules containing an oligonucleosidic and/or oligonucleotidic part, and oligonucleosides and oligonucleotides having chemical modifications such as graftings of hydrophobic molecules.
  • the particle is a microcapsule, a nanocapsule, a microsphere, a nanosphere, a liposome, or any mixture of these particles.
  • the size of the microcapsules or of the microspheres is between 1 and 100 ⁇ m, preferably between 2 and 80 ⁇ m.
  • the size of the nanocapsules or of the nanospheres is between 10 nm and less than 1 ⁇ m, preferably between 20 and 900 nm.
  • the particle contains at least one active principle, which is preferably topically acceptable, and which can be released under the effect of a solar radiation and/or UV radiation.
  • the invention has the advantageous particularity that the release of the active principle is effected in relation with the intensity of the energy of the radiation.
  • the invention notably enables the release of a sufficient amount of the active principle in a period of about 24 hours after exposure to a radiation of energy sufficient to cause such a release.
  • the release of a sufficient amount of the active principle is effected during an exposure to a radiation of energy greater than 200 kJ/m2, preferably greater than 4,000 kJ/m2.
  • the invention is notably particularly pertinent for encapsulating a liposoluble or hydrosoluble active principle.
  • the active principle is selected from the group consisting of antioxidants, moisturizing agents, solar filters, perfumes, vitamins, co-enzymes, anti-bacterial agents and preservatives, moisturising actives, ⁇ anti-age>> actives, skin barrier tonics namely helping to restore the skin barrier, active principles which protect from a solar radiation and/or UV radiation, active principles which repair the skin during or after an exposure to a solar radiation and/or UV radiation, as well as any active principle the progressive release of which is necessary to control by linking it to the dose of radiation, and notably of UV, applied, active principles which are badly absorbed by the skin, and one of a mixture of these.
  • the invention can notably be realized by cross-linking, notably by interfacial polymerization, with a cross-linking agent notably selected from the group consisting of dichlorides of organic acids such as fumaric acid, sebacic acid, azelaic-acid, terephthalic acid, phthalic acid, succinic-acid, glutaric acid, adipic acid, dichlorides of tricarboxylic acids, such as citric acid, trichlorides of tricarboxilic acids, such as citric acid, acid dianhydrides, diisocyanates, dialdehydes such as glutaraldehyde and formaldehyde, and di-epoxides.
  • a cross-linking agent notably selected from the group consisting of dichlorides of organic acids such as fumaric acid, sebacic acid, azelaic-acid, terephthalic acid, phthalic acid, succinic-acid, glutaric acid, adipic acid, dich
  • the invention relates to a cosmetic, dermatological, pharmaceutical, or agri-food composition
  • a cosmetic, dermatological, pharmaceutical, or agri-food composition comprising at least one particle, as defined above, or one of the various possible mixtures of these particles.
  • this composition further comprises an excipient, such as an agent selected from the group consisting of preservatives, gelling agents, which are hydrophilic or lipophilic, solvents, emulsifiers, co-emulsifiers, moisteners, thickeners, stabilizers, antioxidants, solar filters, pigments, colorant materials, organic or inorganic fillers, perfumes, and odor absorbers.
  • an excipient such as an agent selected from the group consisting of preservatives, gelling agents, which are hydrophilic or lipophilic, solvents, emulsifiers, co-emulsifiers, moisteners, thickeners, stabilizers, antioxidants, solar filters, pigments, colorant materials, organic or inorganic fillers, perfumes, and odor absorbers.
  • this composition is formulated in a form which is acceptable cosmetically, dermatologically, pharmaceutically, for agri-food or agro-industrially, notably in a form selected from the group consisting of a solution, which is aqueous or oily, a cream or an aqueous gel or an oily gel, notably in a pot or in a tube, notably a shower gel, a shampoo; a milk; an emulsion, a microemulsion or a nanoemulsion, which is notably oil-in-water or water-in-oil or multiple or silicone-containing; a lotion, notably in a glass bottle, a plastic bottle, a measure bottle, an aerosol, or in a spray; an ampoule; a liquid soap; a dermatological bar; an ointment; a foam; and an anhydrous product, preferably which is liquid, pasty or solid, e.g. in a form of a stick, notably in a form of lipstick.
  • a solution which
  • the invention relates to the use of particles as defined above, or of a composition as defined above, for releasing an active, during an exposure of the particles to an electromagnetic wave, notably the wavelength of which is in the spectrum of the wavelengths emitted by the sun, notably in relation with the intensity of the energy of the electromagnetic wave.
  • these particles or compositions are used for protecting or repairing the skin during or after an exposure to such electromagnetic waves, notably to a solar and/UV radiation.
  • the active is rapidly released at the same moment as when the skin needs it.
  • These particles or compositions can also be used advantageously for releasing, according to the intensity of the energy of the radiation, an active principle, which is either badly tolerated by the skin, or which would penetrate too rapidly into the skin, such as a solar filter, notably with the aim of releasing this active only in case of need.
  • the invention can in fact be used for slowing down to the maximum the penetration of an active that is known to be very rapidly absorbed or is badly “tolerated” by the skin, such as a solar filter for example. From this fad, this active will be released only in case of real need, i.e. notably in case of a prolonged solar exposure.
  • an active that is known to be very rapidly absorbed or is badly “tolerated” by the skin, such as a solar filter for example. From this fad, this active will be released only in case of real need, i.e. notably in case of a prolonged solar exposure.
  • the invention can also be used progressively releasing an active throughout the day, either with a view to improving its release throughout the whole day, e.g. with a view to the progressive release of an anti-oxidant for protecting the skin, of a substance enabling the reconstruction of the skin barrier for a progressive reconstruction, of a perfume for a release throughout the whole day, of UV filters for a progressive protection against UVs, of moisturising active principles for a long term moisturization, of anti-age actives for a release throughout the whole day, of anti-microbial agents or of preservatives for anti-microbial effects arising progressively throughout the whole day, etc. . . . From this fact, these actives encapsulated in such particles will be released only in case of real need, i.e. notably in case of a prolonged solar exposure.
  • the invention finds a cosmetic, dermatological or pharmaceutical use essentially by application of these particles or compositions via the topical route on a living being, notably on a human being or on an animal. From this fact, the invention can very advantageously be implemented by incorporating, within the particles, active principles enabling protecting or repairing the skin of a subject in a controlled manner as a function of the solar exposure.
  • a agri-food or agro-industrial use of these particles or compositions notably by application around a seed, on the leaves of a plant, on the entire plant, on a part of the plant, on the base of the plant, on the roots of the plant, or around the plant, can advantageously be found in releasing an active principle said seed or plant of which would be in need thereof, or for providing an indication of a need of said seed or plant (fertilizer, pesticide, herbicide, for example).
  • the invention relates to a method of cosmetic care, characterised in that particles as defined above, or a composition as defined above, containing at least one a cosmetic active principle, is/are applied on the skin, and/or on the body hairs, and/or on the hair, and in that the particles, which are alone or in a mixture so as to form a cosmetic composition, degrade during an exposure to the sun, and release at least one active principle, thus enabling providing an indication of the effects of the sun on the skin, and/or on the body hairs, and/or on the hair, and/or providing a beneficial effect to the skin, and/or to the body hairs and/or to the hair, during an exposure to the sun.
  • the invention relates to a method of treatment of a plant, characterised in that particles, as defined above, or a composition as defined above, containing at least one food active principle, is/are applied around the seed, on the leaves of a plant, on the entire plant, on a part of the plant, on the base of the plant, on the roots of the plant, or around the plant, and in that the particles, which are alone or in a mixture so as to form a agri-food composition, degrade during an exposure to the sun, and thus release at least one active principle enabling providing an indication to the plant of the effects of the sun and/or treating at least one harmful effect linked to an exposure to the sun and/or improving the benefits linked to an exposure to the sun.
  • an electromagnetic wave>> the inventors mean a whole of electromagnetic waves which are able or not to have the same wavelength.
  • the wavelengths emitted by the sun are notably comprised as being the electromagnetic wavelengths which correspond to the range of infra-red, but more particularly ultraviolet waves (UV), which roughly corresponds to but in no way are limited to, wavelengths of between 10 ⁇ 8 and 4.10 ⁇ 7 m and visible waves, which also roughly correspond to, but are in no way limited to, wavelengths of between 400 and 800 nm.
  • UV ultraviolet waves
  • FIG. 1 is a microscopic view of microspheres prepared according to the invention (magnification ⁇ 20). This microscopic view is made before carrying out an irradiation;
  • FIG. 2 corresponds to the microspheres according to the invention, which is observed after irradiation under solar light (solar irradiator) at a dose of 3,800 kJ/m 2 .
  • solar light solar irradiator
  • FIG. 3 represents a microscopic view (magnification ⁇ 20) of microspheres prepared according to a prior art technique and have been prepared according to the method of Example 3;
  • FIG. 4 represents the microspheres observed in FIG. 3 after irradiation under solar light (solar irradiator) at a dose of 3,800 kJ/m 2 .
  • FIG. 4 enables observing that there is no degradation of the microspheres.
  • composition of the invention used for making FIGS. 1 and 2 corresponds to a preparation made according to Example 1.
  • control composition used for making FIGS. 3 and 4 corresponds to a preparation made according to Example 3.
  • microcapsules recovered have a size of between 2 and 80 ⁇ m in diameter; they are then optionally placed in suspension in a gel (hydrophilic, lipophilic, or silicone type) optionally containing preservatives, which can be used in any cosmetic or pharmaceutical preparation.
  • a gel hydrophilic, lipophilic, or silicone type
  • preservatives which can be used in any cosmetic or pharmaceutical preparation.
  • These microcapsules can also be dried (by atomization for example) and then sterilized by radiation, in order to be used in any type of application wherein the dry forms might be preferred (use in oily or silicone solutions for example).
  • microcapsules recovered are then optionally placed in suspension in a gel (hydrophilic, lipophilic, or silicone type) containing or not containing preservatives, which can be used in any cosmetic or pharmaceutical preparation.
  • a gel hydrophilic, lipophilic, or silicone type
  • preservatives which can be used in any cosmetic or pharmaceutical preparation.
  • These microcapsules can also be dried (by atomization for example) and then sterilized by radiation, in order to be used in any type of application wherein the dry forms might be preferred (use in oily or silicone solutions for example).
  • microspheres were made from collagen and glycosaminoglycans according to the patent FR 2,642,329 (U.S. Pat. No. 5,395,620) (COLETICA), from plant proteins from wheat or from lupin according to the patent FR 2,766,090 (U.S. Pat. No. 5,912,016) (COLETICA), or from polysaccharides such as acacia according to the patent FR 2,688,422 (U.S. Pat. No. 5,562,924) (COLETICA).
  • a liposoluble colorant having an absorption peak at 582 nm, was introduced in the oily phase.
  • microspheres prepared in Example 1, as well as those prepared with the various polymers described above, are diluted to 25% (w/w) in a carbomer gel. 87.5 g of pure laboratory water containing 0.5% of sodium tricitrate are then added to 12.5 g of the gel thus obtained. The pH of the suspension of spheres thus obtained is adjusted to 5 with 1N HCl.
  • the solar irradiator used by virtue of its xenon arc lamp, enables re-creating the solar radiation the most accurately as possible (spectral range 300-3,000 nm).
  • Table 1 gives the average daily irradiations received at various points of the earth's globe (energy measured between 300 and 800 nm).
  • the various microcapsules prepared received a solar irradiation of 3,804 kJ/M 2 and then the percentage opening under solar irradiation was calculated.
  • microcapsules prepared from DNA i.e. according to Example 1, have the most opening under solar irradiation.
  • microcapsules were prepared from collagen and marine glycosaminoglycans, from a mixture of polysaccharides and plant proteins extracted from acacia and from marine DNA according to the protocol described in Example 1.
  • microcapsules were then irradiated at various doses and the amount of oil released was quantified according to the technique described in Example 3. The percentages opening obtained are given in Table 4. TABLE 4 Percentages opening of various types of microcapsules as a function of several doses of solar energy Irradiation Irradiation Irradiation 1,243 kJ/m2 2,467 kJ/m2 3,804 kJ/m2 4,927 kJ/m2 Microcapsules based on 1.7 +/ ⁇ 1.5 1.6 +/ ⁇ 1.3 7.5 +/ ⁇ 3.2 16.6 +/ ⁇ 8.8 marine collagen Microcapsules based on 0 +/ ⁇ 0.6 0.3 +/ ⁇ 2.7 3.5 +/ ⁇ 1.5 6.7 +/ ⁇ 3.4 polysaccharides and proteins extracted from acacia gum Microcapsules based on 11.9 +/ ⁇ 4.5 18.3 +/ ⁇ 3 29.7 +/ ⁇ 5.8 79.9 +/ ⁇ 0.1 marine DNA
  • the spheres based on DNA which were prepared according to Example 1, and control microspheres prepared from collagen and glycosaminoglycans according to Example 5, are irradiated under solar light (solar irradiator), at a dose of 2,800 kJ/m 2 .
  • solar irradiator solar irradiator
  • the products of the invention (FIGS. 1 and 2) as well as the control microspheres (FIGS. 3 and 4) are observed before and after irradiation: it is observed that only the microspheres of the invention have a membrane which is degraded under the action of the UV, the membrane of the control microspheres being not at all degraded under the same conditions.
  • step b) of Example 1 the emulsification step is carried out under a more or less rapid agitation, with agitators of mechanical agitator type of Rayneri type (0-8,000 rpm) or Ultraturrax type (up to 20,000 rpm) in the presence or not of emulsifying agents, and the size of the emulsion (thus of the microcapsules) can be fixed between 1 ⁇ m and 100 ⁇ m in a very precise manner. Otherwise, the other steps of Example 1 are kept identical.
  • step d) of Example 2 the emulsification step is carried out under a more or less rapid agitation, with agitators of mechanical agitator type of Rayneri type (0-8,000 rpm) or Ultraturrax type (up to 20,000 rpm) in the presence of an increasing amount of emulsifying agent of Span 85 (ICI) type, and the size of the emulsion (thus of the microspheres) can be fixed between 1 ⁇ m and 100 ⁇ m in a very precise manner. Otherwise, the other steps of Example 2 are kept identical.
  • step b) of Example 1 the emulsification step is carried out with the aid of a commercial high pressure homogenizer (APV, Alpha-Laval, etc. . . . ), generally used in the homogenization of food products, in the presence or not of emulsifying agents.
  • the homogenization pressure is between 800 bars and 3,000 bars.
  • the size of the nanocapsules thus formed is between 50 nm (high pressures) and 900 nm (lower pressures). Otherwise, the other steps of Example 1 are kept identical.
  • step d) of Example 2 the emulsification step is carried out with the aid of a commercial high pressure homogenizer (APV, Alpha-Laval, etc. . . . ), generally used in the homogenization of food products, in the presence or not of emulsifying agents.
  • the homogenization pressure is between 800 bars and 3,000 bars.
  • the size of the nanocapsules thus formed is between 50 nm (high pressures) and 900 nm (lower pressures). Otherwise, the other steps of Example 2 are kept identical.
  • RNA of marine origin which is commercially available (Javenech, France) is used, in proportions which are identical to those used in Example 1, such as, for example, RNA extracted from fish milt.
  • the particles obtained are sensitive to UVs and hydrolyze under solar irradiation.
  • the particles obtained are sensitive to UVs and hydrolyze under solar irradiation.
  • the particles obtained are of smaller size than the particles obtained in Example 1 (1 to 50 ⁇ m), and are sensitive to UVs and hydrolyze under solar irradiation.
  • nucleotides or nucleosides which can be used in the invention, the following are cited: oligo-antisenses, polyamide nucleic acids (PNA), RNAs called Small Interfering RNA (siRNAs), mRNAs, hybrid molecules containing a oligonucleosides and oligonucleotides part, and oligonucleosides and oligonucleotides having chemical modifications such as graftings of hydrophobic molecules for example.
  • PNA polyamide nucleic acids
  • siRNAs Small Interfering RNA
  • mRNAs hybrid molecules containing a oligonucleosides and oligonucleotides part
  • oligonucleosides and oligonucleotides having chemical modifications such as graftings of hydrophobic molecules for example.
  • dichlorides of organic acids such as fumaric acid, sebacic acid, azelaic acid, terephthalic acid, phthalic acid, succinic acid, glutaric acid, adipic acid, dichlorides of tricarboxylic acids, such as citric acid, trichlorides of tricarboxilic acid, such as citric acid, acid dianhydrides,
  • dialdehydes such as glutaraldehyde, formaldehyde
  • the particles obtained are sensitive to the UVs and hydrolyze under solar irradiation.
  • RNA of marine origin which is commercially available, is used in amounts which are identical to those used in Example 15.
  • the particles obtained are sensitive to UV and hydrolyze under solar irradiation.
  • an anti-oxidant such as tocopherol is released progressively under UV irradiation (40% after 3 hours, 80% after 6 hours of irradiation) for a UV-adapted protection of the skin.
  • the particles obtained are sensitive to UV and hydrolyze under solar irradiation.
  • a solar filter such as Parsol MCX is released progressively under UV irradiation (60% after 3 hours, 96% after 6 hours of irradiation) for a UV-adapted protection of the skin.
  • the particles obtained are sensitive to UVs and hydrolyze under solar irradiation.
  • nucleotides or nucleosides which can be used in the invention, the following are cited: oligo-antisenses, polyamide nucleic acids (PNA), RNAs called Small Interfering RNA (siRNAs), mRNAs, hybrid molecules containing a oligonucleosides and oligonucleotides part, and oligonucleosides and oligonucleotides having chemical modifications such as graftings of hydrophobic molecules for example.
  • PNA polyamide nucleic acids
  • siRNAs Small Interfering RNA
  • mRNAs hybrid molecules containing a oligonucleosides and oligonucleotides part
  • oligonucleosides and oligonucleotides having chemical modifications such as graftings of hydrophobic molecules for example.
  • a commercial perfume (Dragoco) is released progressively under UV irradiation (odor always perceptible as from UV irradiation even 6 hours after a mono-application), for a UV-adapted release on the skin.
  • Formulation 19a A Water qsp 100 Butylene Glycol 2 Glycerol 3 Sodium Dihydroxycetyl 2 Phosphate, Isopropyl Hydroxycetyl Ether B Glycol Stearate SE 14 Triisononaoin 5 Octyl Cocoate 6 C Butylene Glycol, 2 Methylparaben, Ethylparaben, Propylparaben, pH adjusted to 5.5 D Products of the invention 0.01-10%
  • Formulation 19b A Water qsp 100 Butylene Glycol 2 Glycerol 3 Polyacrylamide, Isoparaffin, 2.8 Laureth-7 B Butylene Glycol, 2 Methylparaben, Ethylparaben, Propylparaben; Phenoxyethanol, 2 Methylparaben, Propylparaben, Butylparaben, Ethylparab
  • Toxicology tests were carried out on the microcapsules obtained according to Example 1, diluted to 25% in a 0.4% carbomer gel.
  • the tests comprised an evaluation of the primary skin and ocular irritation in the rabbit, a study of the absence of abnormal toxicity by single oral administration in the rat and a research of the sensitizing power in the guinea pig.
  • the preparation described was administered in one batch orally at the dose of 5 g/Kg of body weight, to 5 male rats and 5 female rats according to a protocol inspired from the directive of the OECD No. 401 of 24 th Feb. 1987 and adapted to cosmetic products.
  • the LD0 and LD50 are found to be greater than 5,000 mg/Kg. The preparation tested is therefore not classed amongst the preparations which are dangerous by ingestion.
  • the preparation is classed as non-sensitizing by contact with the skin.
  • the product is applied under an occlusive patch for 24 hours, and is then re-applied under patch for 2 days for a total of 9 applications (induction phase). After a period of 2 weeks, other patches containing the product are applied onto the skin of the volunteers and are left in contact for 24 hours. The clinical signs of irritation and skin sensitization are evaluated 24, 48 and 72 hours after the removal of the patch (challenge phase).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Nanotechnology (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medical Informatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Biomedical Technology (AREA)
  • Toxicology (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
US10/346,690 2002-12-24 2003-01-15 Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation Abandoned US20040121019A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/069,922 US8957001B2 (en) 2002-12-24 2011-03-23 Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0216637 2002-12-24
FR0216637A FR2848854B1 (fr) 2002-12-24 2002-12-24 Particules comprenant un biopolymere degradable sous l'effet d'une onde electromagnetique telle qu'emise par un rayonnement solaire

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/069,922 Continuation US8957001B2 (en) 2002-12-24 2011-03-23 Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation

Publications (1)

Publication Number Publication Date
US20040121019A1 true US20040121019A1 (en) 2004-06-24

Family

ID=8871579

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/346,690 Abandoned US20040121019A1 (en) 2002-12-24 2003-01-15 Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation
US13/069,922 Expired - Fee Related US8957001B2 (en) 2002-12-24 2011-03-23 Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation

Family Applications After (1)

Application Number Title Priority Date Filing Date
US13/069,922 Expired - Fee Related US8957001B2 (en) 2002-12-24 2011-03-23 Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation

Country Status (8)

Country Link
US (2) US20040121019A1 (de)
JP (2) JP4503932B2 (de)
KR (1) KR100550303B1 (de)
CH (1) CH694072A5 (de)
DE (1) DE10320604B4 (de)
ES (1) ES2228250B1 (de)
FR (1) FR2848854B1 (de)
GB (1) GB2396556B (de)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090035236A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent
US20090035243A1 (en) * 2007-07-31 2009-02-05 Anna Czarnota Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
US20090035240A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
US20090035237A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Silicone Surfactant
US20090035242A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
US20090068132A1 (en) * 2007-09-08 2009-03-12 Daniela Bratescu Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same
US20100233022A1 (en) * 2009-03-16 2010-09-16 Ondine International Ltd. Composition for photodynamic disinfection
WO2013155691A1 (en) * 2012-04-19 2013-10-24 General Electric Company A method to stabilize liposome emulsions for biocidal delivery
US9078393B1 (en) 2012-03-13 2015-07-14 Activation Technologies, LLC Activated-release fertilizer, pesticides, and other granules, germination-activated seeds, and methods of making and using same
US9549891B2 (en) 2012-03-19 2017-01-24 The Procter & Gamble Company Superabsorbent polymers and sunscreen actives for use in skin care compositions
US10285926B2 (en) 2015-06-29 2019-05-14 The Procter & Gamble Company Superabsorbent polymers and starch powders for use in skin care compositions
CN110769811A (zh) * 2017-05-04 2020-02-07 奥特昂股份有限公司 用于透皮递送活性分子的装置、该装置的用途和该装置及其组件的生产方法
US10901315B2 (en) 2017-08-11 2021-01-26 Procter & Gamble International Operations Sa Photosensitive microcapsules
US11051444B2 (en) * 2017-10-24 2021-07-06 Miles Mitchell Seed activation system and method
WO2025082968A1 (en) * 2023-10-17 2025-04-24 Firmenich Sa Ribonucleic acid-based microcapsules

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007077212A (ja) * 2005-09-12 2007-03-29 Masamitsu Nagahama 樹脂材料、樹脂材料の製造方法、粒状物の使用
JP2008266324A (ja) * 2007-03-29 2008-11-06 Kose Corp リポソーム組成物及び該リポソーム組成物を含有した皮膚外用剤
JP5182751B2 (ja) * 2008-05-26 2013-04-17 国立大学法人群馬大学 化粧品材料及びその製造方法
CA2768242C (en) * 2009-07-16 2015-11-17 Georgia Health Sciences University Research Institute, Inc. Porous-wall hollow glass microspheres as carriers for biomolecules
FR2954702B1 (fr) 2009-12-31 2013-07-05 Basf Beauty Care Solutions F Agent stimulant l'expression de loxl
EP2822382B1 (de) 2011-03-03 2018-12-19 The University of Queensland Blattdünger
US11021408B2 (en) 2011-03-03 2021-06-01 The University Of Queensland Nanoparticle fertilizer
AU2012222876B2 (en) * 2012-03-05 2016-09-15 The University Of Queensland Foliar fertiliser
JP6185990B2 (ja) * 2012-07-10 2017-08-23 コーニンクレッカ フィリップス エヌ ヴェＫｏｎｉｎｋｌｉｊｋｅ Ｐｈｉｌｉｐｓ Ｎ．Ｖ． 毛髪の選択的加熱による容器からの分子の放出
CZ2012932A3 (cs) * 2012-12-19 2013-12-04 C2P S.R.O. Prípravek pro postupné uvolnování kyseliny nikotinové a/nebo nikotinamidu
JP6359947B2 (ja) * 2014-10-28 2018-07-18 富士フイルム株式会社 日焼け止め化粧料
IT202000030071A1 (it) * 2020-12-15 2021-03-15 Service Biotech S R L Realizzazione di un dispositivo di segnalazione dermatologico simile ad un patch test per l’identificazione di reazione allergica di medicamenti, preventiva alla somministrazione al paziente.

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4766870A (en) * 1986-04-30 1988-08-30 Honda Giken Kogyo Kabushiki Kaisha Method of air/fuel ratio control for internal combustion engine
US5376379A (en) * 1990-10-17 1994-12-27 Pierre Fabre Cosmetique Liposomes of thermal waters stabilized in a DNA gel
US5395620A (en) * 1989-01-31 1995-03-07 Coletica Biodegradable microcapsules having walls composed of crosslinked atelocollagen and polyholoside
US5562924A (en) * 1992-03-11 1996-10-08 Coletica Polysaccharide wall microcapsules containing primary alcohol functions and compositions containing same
US5912016A (en) * 1997-07-15 1999-06-15 Coletica Particles of crosslinked plant proteins and the process for their preparation
US6348218B1 (en) * 1999-10-04 2002-02-19 Invent Resources, Inc. Self dosing skin preparation
US20030219384A1 (en) * 1998-03-19 2003-11-27 Edwin Donath Production of nanocapsules and microcapsules by layer-wise polyelectrolyte self-assembly

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2020976B (en) * 1977-09-22 1982-08-18 Battelle Development Corp Microbial inseticides
JPS57501579A (de) * 1980-09-15 1982-09-02
DE3630693A1 (de) * 1985-09-09 1987-03-12 Fuji Photo Film Co Ltd Photochemisch abbaubare mikrokapseln
US5089269A (en) * 1987-11-07 1992-02-18 Shiseido Company Ltd. Cosmetic containing fine soft microcapsules
JPH0429915A (ja) * 1990-05-24 1992-01-31 Sunstar Inc 光破砕性リポソーム含有皮膚化粧料
US5733531A (en) * 1991-02-05 1998-03-31 Sunsmart, Inc. Composite UV sunblock compositions
JPH059107A (ja) * 1991-06-28 1993-01-19 Noevir Co Ltd 光応答性マイクロカプセル、及びこれを配合した化粧料並びに皮膚外用剤
JPH05155784A (ja) * 1991-12-11 1993-06-22 Nippon Kayaku Co Ltd 徐放性製剤
FR2694895B1 (fr) 1992-08-20 1994-11-10 Coletica Procédé de fabrication de microparticules en émulsion par modification de la composition chimique de la phase dispersée après émulsification.
US5498421A (en) 1993-02-22 1996-03-12 Vivorx Pharmaceuticals, Inc. Composition useful for in vivo delivery of biologics and methods employing same
AU3004695A (en) * 1994-07-08 1996-02-09 Apogen Nucleic acid filters
DE59707744D1 (de) * 1996-10-23 2002-08-22 Sueddeutsche Kalkstickstoff Verfahren zur herstellung von biologisch aktiven polymernanopartikel-nucleinsäure-konjugaten
EP1064087B1 (de) * 1998-03-19 2006-01-25 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Herstellung von nano- und mikrokapseln durch schichtweise polyelektrolyt-selbstassemblierung
CA2329252A1 (en) * 1998-05-21 1999-11-25 Isis Pharmaceuticals Inc. Compositions and methods for topical delivery of oligonucleotides
WO1999065531A1 (en) * 1998-06-18 1999-12-23 Johns Hopkins University School Of Medicine Polymers for delivery of nucleic acids
FR2780901B1 (fr) * 1998-07-09 2000-09-29 Coletica Particules, en particulier micro- ou nanoparticules de monosaccharides et oligosaccharides reticules, leurs procedes de preparation et compositions cosmetiques, pharmaceutiques ou alimentaires en contenant
WO2001039744A2 (en) * 1999-11-30 2001-06-07 The Arizona Board Of Regents On Behalf Of The University Of Arizona Radiation sensitive liposomes
JP3636958B2 (ja) * 2000-03-22 2005-04-06 株式会社カネボウ化粧品 化粧料
AU2452302A (en) * 2000-07-21 2002-02-05 Mark B Lyles Sunscreen formulations containing nucleic acids
EP1211234A3 (de) * 2000-11-29 2003-11-26 Samsung Electronics Co., Ltd. Verfahren zur Herstellung von 1,3-Alkandiolen aus 3-Hydroxyestern
JP5009107B2 (ja) 2007-09-12 2012-08-22 サーパス工業株式会社 サックバックバルブ

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4766870A (en) * 1986-04-30 1988-08-30 Honda Giken Kogyo Kabushiki Kaisha Method of air/fuel ratio control for internal combustion engine
US5395620A (en) * 1989-01-31 1995-03-07 Coletica Biodegradable microcapsules having walls composed of crosslinked atelocollagen and polyholoside
US5376379A (en) * 1990-10-17 1994-12-27 Pierre Fabre Cosmetique Liposomes of thermal waters stabilized in a DNA gel
US5562924A (en) * 1992-03-11 1996-10-08 Coletica Polysaccharide wall microcapsules containing primary alcohol functions and compositions containing same
US5912016A (en) * 1997-07-15 1999-06-15 Coletica Particles of crosslinked plant proteins and the process for their preparation
US20030219384A1 (en) * 1998-03-19 2003-11-27 Edwin Donath Production of nanocapsules and microcapsules by layer-wise polyelectrolyte self-assembly
US6348218B1 (en) * 1999-10-04 2002-02-19 Invent Resources, Inc. Self dosing skin preparation

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9162083B2 (en) 2007-07-31 2015-10-20 Elc Management Llc Linoleic and Linolenic acid esters of resveratrol and cosmetic compositions
US20090035243A1 (en) * 2007-07-31 2009-02-05 Anna Czarnota Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
US20090035240A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
US20090035237A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Silicone Surfactant
US20090035242A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
US9295621B2 (en) 2007-07-31 2016-03-29 Elc Management Llc Emulsion cosmetic compositions containing resveratrol derivatives and silicone surfactant
US20100216879A1 (en) * 2007-07-31 2010-08-26 Maes Daniel H Resveratrol Ferulate Compounds And Compositions
US20090035236A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent
US9180316B2 (en) 2007-07-31 2015-11-10 Elc Management Llc Butyric acid esters of resveratrol and cosmetic compositions
US8080583B2 (en) 2007-07-31 2011-12-20 Elc Management Llc Emulsion cosmetic compositions containing resveratrol derivatives and linear or branched silicone
US8084496B2 (en) 2007-07-31 2011-12-27 Elc Management Llc Resveratrol ferulate compounds and compositions
US8344024B2 (en) 2007-07-31 2013-01-01 Elc Management Llc Anhydrous cosmetic compositions containing resveratrol derivatives
US8362076B2 (en) 2007-07-31 2013-01-29 Elc Management Llc Ascorbic acid esters of resveratrol and cosmetic compositions
US8461200B2 (en) 2007-07-31 2013-06-11 Elc Management Llc Salicylic acid esters of resveratrol and cosmetic compositions
US20100215755A1 (en) * 2007-09-08 2010-08-26 Daniela Bratescu Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same
US9220669B2 (en) 2007-09-08 2015-12-29 Elc Management Llc Resveratrol ferulate compounds, compositions containing the compounds, and methods of using the same
US20090068132A1 (en) * 2007-09-08 2009-03-12 Daniela Bratescu Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same
US8703050B2 (en) * 2009-03-16 2014-04-22 Ondine International Ltd. Composition for photodynamic disinfection
US20100233022A1 (en) * 2009-03-16 2010-09-16 Ondine International Ltd. Composition for photodynamic disinfection
US9078393B1 (en) 2012-03-13 2015-07-14 Activation Technologies, LLC Activated-release fertilizer, pesticides, and other granules, germination-activated seeds, and methods of making and using same
US9839598B2 (en) 2012-03-19 2017-12-12 The Procter & Gamble Company Superabsorbent polymers and sunscreen actives for use in skin care compositions
US9549891B2 (en) 2012-03-19 2017-01-24 The Procter & Gamble Company Superabsorbent polymers and sunscreen actives for use in skin care compositions
WO2013155691A1 (en) * 2012-04-19 2013-10-24 General Electric Company A method to stabilize liposome emulsions for biocidal delivery
CN104245594B (zh) * 2012-04-19 2016-07-06 通用电气公司 稳定用于杀生物剂递送的脂质体乳液的方法
CN104245594A (zh) * 2012-04-19 2014-12-24 通用电气公司 稳定用于杀生物剂递送的脂质体乳液的方法
US10285926B2 (en) 2015-06-29 2019-05-14 The Procter & Gamble Company Superabsorbent polymers and starch powders for use in skin care compositions
CN110769811A (zh) * 2017-05-04 2020-02-07 奥特昂股份有限公司 用于透皮递送活性分子的装置、该装置的用途和该装置及其组件的生产方法
US10901315B2 (en) 2017-08-11 2021-01-26 Procter & Gamble International Operations Sa Photosensitive microcapsules
US11051444B2 (en) * 2017-10-24 2021-07-06 Miles Mitchell Seed activation system and method
WO2025082968A1 (en) * 2023-10-17 2025-04-24 Firmenich Sa Ribonucleic acid-based microcapsules

Also Published As

Publication number Publication date
KR20040057863A (ko) 2004-07-02
CH694072A5 (fr) 2004-07-15
DE10320604B4 (de) 2011-09-01
ES2228250A1 (es) 2005-04-01
JP2004203852A (ja) 2004-07-22
GB2396556B (en) 2005-04-13
FR2848854A1 (fr) 2004-06-25
GB2396556A (en) 2004-06-30
KR100550303B1 (ko) 2006-02-08
US8957001B2 (en) 2015-02-17
ES2228250B1 (es) 2006-02-16
US20120053058A1 (en) 2012-03-01
JP4503932B2 (ja) 2010-07-14
JP2010031042A (ja) 2010-02-12
DE10320604A1 (de) 2004-07-15
FR2848854B1 (fr) 2005-03-18
GB0303217D0 (en) 2003-03-19

Similar Documents

Publication Publication Date Title
US8957001B2 (en) Particles comprising a biopolymer which is degradable under the effect of an electromagnetic wave as emitted by a solar radiation
Dhawan et al. Cosmetic nanoformulations and their intended use
EP0447318B1 (de) Zusammensetzung zur kosmetischen und/oder pharmazeutischen Behandlung der obersten Epidermisschicht durch topische Anwendung auf der Haut und das entsprechende Herstellungsverfahren
US5961990A (en) Cosmetic particulate gel delivery system and method of preparing complex gel particles
US5993831A (en) Composition providing a lasting cosmetic and/or pharmaceutical treatment of the upper epidermal layers by topical application on the skin
US9849089B2 (en) Hydrogel particle coated with lipid and method for manufacturing same
AU651191B2 (en) Sun filter microcapsules, the cosmetic and pharmaceutical compositions containing them and their use
JP2935518B2 (ja) タツナミ草の抽出物またはこの抽出物の少なくとも一成分と、特に抗アレルギー性、抗炎症性、抗老化性組成物からなる皮膚病学的組成物化粧用または製薬用組成物とを取り込んだ水和脂質ラメラ相またはリポソームにもとづく組成物
JP4758915B2 (ja) 多重層リポソームおよびその製造方法
KR20110021853A (ko) 마이크로캡슐화된 착색제를 포함하는 국소 적용용 조성물
KR20170076223A (ko) 하이드로젤 캡슐, 이의 제조방법 및 이를 포함하는 화장료 조성물
Shah et al. Advanced development of a non-ionic surfactant and cholesterol material based niosomal gel formulation for the topical delivery of anti-acne drugs
Rohilla et al. Global trends of cosmeceutical in nanotechnology: a review
CN111643377A (zh) 一种汉麻油纳米微胶囊及其制备方法和应用
WO2019111415A1 (ja) カチオン化ベシクル及びその組成物
JP4939936B2 (ja) 生理活性成分を含有する自己集合性高分子ナノ粒子の製造方法、及び得られた自己集合性高分子ナノ粒子を含有する外用剤組成物
Vohra et al. Nano-Transferosomes of Aloe-Vera and Vitamin-E for Management of Psoriasis: An Archetype in Herbal Drug Technology
Sallustio et al. Development and characterization of multifunctional phytonanoemulgels based on licorice extract and biocompatible polymers
Reddy et al. Formulation and evaluation of celecoxib emulgel
Pawar et al. Formulation and Evaluation of Eudragit L-100 based Nanoparticles of Senna for Treatment of Constipation.
KR102827958B1 (ko) 피부흡수 촉진용 히알루론산 나노캡슐, 이의 제조방법 및 이를 포함한 화장료 조성물
JP2004238297A (ja) 抗皮膚ストレス（ストレス防御）用化粧料
Jain et al. Central composite design-based optimization, formulation and characterization of tretinoin-loaded lipoidal cubic-shaped nanocarriers.
Shete et al. Lipid Nanocarriers of Naringin Dispersed Gel for Topical Application: Development, In Vitro, Ex Vivo, and In Vivo Kinetics Evaluations
FR3133994A1 (fr) Utilisation non thérapeutique de dextrines hyperbranchées comme agent apaisant.

Legal Events

Date Code Title Description
AS Assignment

Owner name: COLETICA, FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BONNET, ISABELLE;DE MATTEIS, CHARLOTTE;PERRIER, ERIC;REEL/FRAME:013953/0627

Effective date: 20030205

AS Assignment

Owner name: ENGELHARD LYON SA, FRANCE

Free format text: CHANGE OF NAME;ASSIGNOR:COLETICA SA;REEL/FRAME:018099/0968

Effective date: 20050630

AS Assignment

Owner name: BASF BEAUTY CARE SOLUTIONS FRANCE SAS, FRANCE

Free format text: CHANGE OF NAME;ASSIGNOR:ENGELHARD LYON;REEL/FRAME:020417/0603

Effective date: 20070701

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION