WO2009093812A2 - Capsules de polymère double couche pour la stabilisation de caroténoïdes, procédé de préparation de ces capsules et composition cosmétique les contenant - Google Patents

Capsules de polymère double couche pour la stabilisation de caroténoïdes, procédé de préparation de ces capsules et composition cosmétique les contenant Download PDF

Info

Publication number
WO2009093812A2
WO2009093812A2 PCT/KR2008/007645 KR2008007645W WO2009093812A2 WO 2009093812 A2 WO2009093812 A2 WO 2009093812A2 KR 2008007645 W KR2008007645 W KR 2008007645W WO 2009093812 A2 WO2009093812 A2 WO 2009093812A2
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
polymer
capsule
carotenoid
Prior art date
Application number
PCT/KR2008/007645
Other languages
English (en)
Other versions
WO2009093812A3 (fr
Inventor
Yong Jin Kim
Ji Hye An
Chang Hoon Park
Jun Cheol Cho
Original Assignee
Amorepacific Corporation
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 Amorepacific Corporation filed Critical Amorepacific Corporation
Priority to JP2010540575A priority Critical patent/JP5745856B2/ja
Priority to CN2008801233158A priority patent/CN101910256B/zh
Publication of WO2009093812A2 publication Critical patent/WO2009093812A2/fr
Publication of WO2009093812A3 publication Critical patent/WO2009093812A3/fr

Links

Classifications

    • 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
    • A61Q19/08—Anti-ageing preparations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • 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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/12—Making microcapsules or microballoons by phase separation removing solvent from the wall-forming material solution
    • B01J13/125—Making microcapsules or microballoons by phase separation removing solvent from the wall-forming material solution by evaporation of the solvent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening
    • B01J13/22—Coating
    • 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
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • 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
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/63—More than one coating

Definitions

  • the present invention relates to a double-layered polymer capsule for stabilizing a carotenoid such as ⁇ - carotin and a method for preparing the same, and a cosmetic composition comprising the same. More particularly, the present invention relates to a polymer capsule prepared by encapsulating a carotenoid susceptible to oxidation in a cationic polymer and allowing the cation group existing on the outer part of the primarily prepared capsule to self- assemble with an anionic polymer shell to form a core-shell type double-layered structure.
  • Korean Patent Laid-Open Publication No. 2004- 0020470 has disclosed a composition comprising a carrot extract in a small amount since pure ⁇ -carotin could not be introduced into the formulation.
  • U.S. Patent No. 5,034,228 has disclosed a cosmetic composition and dermatological composition applying a liposome containing ⁇ -carotin.
  • U.S. Patent No. 3,998,753 has disclosed a cosmetic composition applying an emulsion of a carotenoid including ⁇ -carotin with SLS (sodium lauryl sulfate) and U.S. Patent No.
  • 6,827,941 has disclosed a make-up preparations applying ⁇ -carotin as a colorant.
  • carotenoids such as ⁇ -carotin in various forms into cosmetic and dermatological compositions.
  • these conventional methods have limitedly proposed the use of the carotenoids as a simple extract in an extremely small amount, the use of the carotenoids with a solubility improved in a cosmetic composition, or the use of the carotenoids as an ingredient of a make-up composition. That is, such conventional methods have not yet proposed a solution to a problem associated with the stabilization of the carotenoids.
  • the present inventors have conducted studies to stabilize a useful active material in a polymer particle, and as a result, have developed a double-layered polymer capsule comprising: a core formed of a carotenoid; a cationic polymer layer surrounding the core; and an anionic polymer layer coated on the surface of the cationic polymer. Based on this development, the present invention has been completed.
  • the present inventors have prepared a core-shell type double-layered polymer capsule by encapsulating a carotenoid including ⁇ -carotin in a cationic polymer and adsorbing a self-assembling anionic polymer to an cationic group existing on the outer part of the particle. Accordingly, the present invention relates to a double- layered polymer capsule for stabilizing a carotenoid susceptible to oxidation and a method for preparing the same. The method comprises the steps of preparing a cationic polymer capsule containing a carotenoid and coating the surface of the capsule with an anionic polymer.
  • the methods for stabilizing an unstable active material by using polymer particles have been widely studied but the encapsulation of the active material in the polymer particles cannot simply achieve the complete stabilization.
  • the polymers can be expanded by water, surfactants, oil and the like in the cosmetic formulation, whereby the unstable active material can slowly flow out to the outside of the particles over a long period of time.
  • a core-shell type double-layered capsule is prepared by encapsulating a carotenoid in a polymer having a cationic functional group for primary stabilization of the carotenoid and adsorbing an anionic polymer to a cationic group exposed on the outer part of the primarily prepared polymer capsule by self- assembling to reinforce the interception of the polymer capsule.
  • the useful active material is completely stabilized inside the capsule and is prevented from contacting with the outer environment and flowing out of the capsule.
  • the protection of degeneration of the carotenoid by antioxidants used for stabilization of the carotenoid is maximized.
  • the method according to the present invention includes a step to encapsulate a carotenoid in a polymer having a cationic functional group.
  • the polymer having a cationic functional group is a random copolymer of a monomer having a cationic functional group and a monomer having a hydrophobic group and has a molecular weight of 10,000 to 1, 000, OOOg/mol .
  • the monomer having a cationic functional group includes 2-vinylpyridine, 3- vinylpyridine, 4-vinylpyridine, acrylamide,
  • the monomer having a cationic functional group is preferably added in an amount of 0.1 to 30% by weight based on the total molecular weight of the cationic polymer.
  • the monomer having a cationic functional group is added in an amount of less than 0.1% by weight, water- dispersed nano particles are not formed.
  • the monomer having a cationic functional group is added in an amount of more than 30% by weight, the solubility in water can be increased and thus, the added amount is limited to prevent dissolution in water according to pH.
  • the monomer having a hydrophobic group of the cationic polymer is a monomer capable of copolymerizing with the monomer having a cationic functional group.
  • examples of the monomer having a hydrophobic group includes stylene, p- or m- methylstylene, p- or m-ethylstylene, p- or m-chlorostylene, p- or m-chloromethylstylene, p- or m-t-butoxystylene, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2- ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, 2- hydroxyethyl (meth) acrylate, polyethylene glycol (meth) acrylate, methoxypoly
  • the polymerization of the copolymer having a cationic functional group is performed by emulsifier-free emulsion polymerization, including the following steps.
  • a mixture of the monomer having a cationic functional group and the monomer having a hydrophobic is added to a solution containig 2, 2 ' -azobis (2- methylpropioneamidine) dihydrochloride as a initializer in water and stirred at 250rpm in a nitrogen atmosphere at a temperature of 70 ° C for 4 hours to obtain a polymer latex.
  • sodium chloride is added to obtain a precipitate, which is then re-crystallized from acetone/water to remove unreacted monomers.
  • the precipitation with sodium chloride is repeated several times.
  • the precipitate is filtrated, washed several times and dried in a vacuum oven to obtain the cationic polymer as powder.
  • the method for preparing the capsule is preferably performed by the conventional nano-precipitation method, which includes dissolving a carotenoid and the polymer having a cationic functional group in a suitable organic solvent, particularly, a water- miscible non-toxic solvent having a vapor pressure lower than water and a high volatility (typically, alcohol/acetone) (oil phase) ; mixing the water phase with the oil phase while stirring at a predetermined rate to obtain an emulsion by self-assembling; and volatilizing the oil phase to obtain the polymer capsule in the water phase.
  • the mixing ratio of the cationic polymer to the carotenoid is preferably in 1:0.01 to 1:1.
  • the surface property of the carotenoid determines the surface property of the prepared cationic polymer capsule, causing precipitation and coagulation by high crystallizability of the carotenoid upon the preparation of the capsule. Also, when the carotenoid is used in an amount of less than 0.01 fold of the cationic polymer, it cannot express its effects in the final cosmetic composition.
  • Representative examples of the carotenoid which can be supported include ⁇ 3 -carotin, lutein, lycopene, zeaxanthin, astaxanthin, capsanthin, ⁇ - cryptoxanthin and the like.
  • An anionic polymer is adsorbed on the surface of the cationic polymer capsule having a carotenoid prepared in the step (1) by self-assembling to prepare a core-shell type double-layered capsule, in which the outer part of the capsule is reinforced by the ionic bond.
  • the anionic polymer has a molecular weight of 10,000 to 1, 000, OOOg/mol and has an anionic functional group such as carboxylic acid and sulphonic acid. Its concrete examples include polystylene sulphonic acid, polyacrylic acid and polymethacrylic acid.
  • the anionic polymer is preferably used in an amount of 100 to 500 parts by weight based on 100 parts by weight of the cationic polymer capsule having the carotenoid supported thereon.
  • the anionic polymer is prepared by mixing monomers to be copolymerized, each in an amount of 50% by weight based on the total weight of the anionic polymer, and performing the copolymerization as described for the cationic polymer.
  • the prepared anionic polymer is dissolved in a KOH solution (pH 11) and added to the aqueous cationic polymer solution to obtain the polymer capsule having a double-layer structure by self-assembling.
  • the polymer capsule having the carotenoid encapsulated therein, prepared as described above, is powder having a particle size of 0.1 to 50 ⁇ m.
  • the core-shell type double-layered polymer capsule according to the present invention is an effective stabilization system capable of maintaining the initial activity of the carotenoid, which is extremely susceptible to oxidation. Also, the polymer capsule according to the present invention can be readily formulated and thus, applied to various compositions.
  • the present invention relates to a cosmetic composition for various formulations comprising the core-shell type double-layered polymer capsule according to the present invention.
  • the polymer capsule is preferably added in an amount of 1 to 10% by weight based on the total weight of the cosmetic composition.
  • the polymer capsule is added in an amount of more than 10% by weight, it affects properties of the formulation, deteriorating stability of the cosmetic composition.
  • the polymer capsule is added in an amount of less than 1% by weight, it is hard to expect the substantial effects.
  • the formulation of the cosmetic composition according to the present invention includes skin toner, skin lotion, massage cream, nourishing cream, gel, pack, essence, lipstick, make-up base, foundation, lotion, ointment, cream, patch and spray, but not limited thereto.
  • the core-shell type double-layered polymer capsule according to the present invention can provide a effective stabilization system capable of maintaining the initial activity of a carotenoid which is extremely susceptible to oxidation and thereby, readily discolored and disodored. Also, the present invention can provide a cosmetic composition of various formulations comprising the core- shell type double-layered polymer capsule which is effective in improving skin wrinkling.
  • FIG. 1 shows a photograph of the double-layered polymer capsule comprising a carotenoid according to the present invention taken by a scanning electron microscope (SEM) .
  • SEM scanning electron microscope
  • a random copolymer having a cationic functional group which had been prepared by the following procedure was used in this Example. 75% by weight, based on the weight of the polymer, of butylmethacrylate was mixed with 25% by weight, based on the weight of the polymer, of (methacrylolyl) ethyl dimethylamine . The mixture was taken into an aqueous solution of 0.5% by weight of 2, 2 ' -azobis (2-methylpropion amidine) dihydrochloride and polymerized in a nitrogen atmosphere at a temperature of 70 ° C for 4 hours while stirring at 250 rpm to obtain a polymer latex.
  • the resulting polymer was obtained as powder by precipitation with sodium chloride, re-crystallized from acetone/water to remove un-reacted monomer, and then, again precipitated with sodium chloride to obtain a product as powder.
  • the product was subjected to the filtration and washing process several times, dried in a vacuum oven to obtain a cationic polymer as powder.
  • a polymer capsule with ⁇ -carotin supported thereon 2 g of the polymer having a cationic functional group prepared by the above-described process and Ig of Lucarotin 30SUN (supplied by BASF) were dissolved in 100ml of acetone. 200ml of distilled water was input into a one-neck round-bottom flask and stirred. The prepared polymer/ ⁇ -carotin/acetone mixture was added to the flask to obtain a self-assembled compound. Then, acetone and a small amount of water were removed by a rotary evaporator to obtain 50 ml of an aqueous polymer solution .
  • An anionic polymer to reinforce the outer part of the prepared cationic polymer capsule was prepared by following the same procedure as described for the cationic polymer, except for substituting the cationic monomer mixture with a mixture of 50% by weight, based on the total weight of the polymer, of methacrylate and 50% by weight, based on the total weight of the polymer, of acrylic acid. Then, 2 g of the resulting anionic polymer was dissolved in a KOH solution (pH 11) and taken into the aqueous cationic polymer solution to obtain the double-layered polymer capsule .
  • a capsule was prepared by following the same procedure as described for Example 1.
  • Example 3 Except for using astaxanthin as an active material instead of ⁇ -carotin, a capsule was prepared by following the same procedure as described for Example 1. Comparative Example 1 Except for not using an anionic polymer, a capsule was prepared by following the same procedure as described for Example 1.
  • Example 1 The double-layered polymer capsule prepared in Example 1 was examined for its morphology by using a scanning electron microscope (SEM). As shown in FIG. 1, it was confirmed that spherical polymer particles were prepared. Also, it was confirmed the prepared polymer particles were powder of solid micro particles having a particle size of 1 to 3OjMi, of which the surface was smooth without holes or unevenness .
  • Formulation 1 In order to confirm the stabilizing effect of the prepared capsule, a soluble formulation of a transparent gel type having the composition of Table 1 below was prepared. The formulation was measured for viscosity by using a viscometer (Brookfield: LVDVII+) at 30 ° C and 12rpm. As a result, it had a viscosity of about 4,000cps. [Table l]
  • each of the prepared specimens was stored at room temperature and in an oven at 40 ° C. After a predetermined period of time, each specimen was measured for the remaining active material by liquid phase chromatography. The result is shown in Table 2. [Table 2]
  • the double-layered polymer capsule in the soluble formulation maintained ⁇ -carotin in an amount of 100% of the initial amount the after 28 days. This meant that the ⁇ -carotin existing in the double-layered polymer capsule showed better stability than the ⁇ -carotin encapsulated only in the cationic polymer and the directly introduced ⁇ -carotin.
  • an opaque gel type lotion was prepared by completely dissolving the oil phase and the water phase in the composition of Table 3 below at 70 ° C, followed by emulsifying at 7,000rpm for 5 minutes.
  • the lotion had a viscosity of about 2,500cps.
  • each of the prepared specimens was stored at room temperature and in an oven at 40 ° C. After a predetermined period of time, each specimen was measured for the remaining active material by liquid phase chromatography. The result is shown in Table 4. [Table 4]
  • the double-layered polymer capsule in the lotion formulation maintained ⁇ -carotin in an amount of 96% or more of the initial amount after 28 days. This meant that the ⁇ - carotin existing in the double-layered polymer capsule showed better stability than the ⁇ -carotin encapsulated only in the cationic polymer and the directly introduced ⁇ -carotin.
  • the double layered polymer capsule according to the present invention had excellent double stabilization system to maintain the chemical structure by encapsulating the ⁇ -carotin in the cationic functional group, prevent the outflow of ⁇ - carotin to the outside of the capsule and intercept the destructive environment by the double-layered polymer matrix of a core-shell structure.
  • each of the prepared specimens was stored at room temperature and in an oven at 40 ° C. After a predetermined period of time, each specimen was measured for the remaining active material by liquid phase chromatography. The result is shown in Table 6. [Table 6]
  • the cationic polymer capsule according to the present invention had excellent stabilizing effect in the other useful active materials such as lycopene and astaxanthin.
  • J3 -carotin in the simple polymer particles was poorly stabilized, since it could contact with the outer environment by expansion of the particles caused by water, oil, surfactants and the like in the cosmetic formulations, whereby it lost its own red color .
  • the core-shell type double-layered polymer capsule prepared in Example 1 showed more excellent stabilization in the formulation than other systems by stabilized the conjugated double bond of ⁇ -carotin from oxygen by the reinforced barrier function of the core-shell structure surrounding ⁇ -carotin and prevented the outflow of J3 -carotin out of the capsule.
  • the core-shell type double-layered polymer capsule prepared in Example 1 reduced the expansion of particles caused by water or oil in the formulation by the matrix shell of the anion polymer along with the inside cationic group fixing ⁇ -carotin and prevented the useful active material from being exposed to the outside environment, which were otherwise oriented toward the capsule wall in the common capsule to be exposed to the outside .

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Manufacturing Of Micro-Capsules (AREA)

Abstract

La présente invention concerne une capsule de polymère double couche pour la stabilisation d'un caroténoïde tel que la ß-carotine, ainsi qu'un procédé de préparation de cette capsule et une composition cosmétique la comprenant. Plus particulièrement, l'invention concerne une capsule de polymère obtenue par préparation d'une capsule de polymère cationique contenant un caroténoïde et par revêtement de la surface de la capsule avec un polymère anionique. La capsule de polymère double couche de la présente invention est un système de stabilisation permettant prévenir la dégradation d'une matière active par l'environnement extérieur agressif, et assure une protection efficace des matières sensibles à l'oxydation.
PCT/KR2008/007645 2007-12-27 2008-12-24 Capsules de polymère double couche pour la stabilisation de caroténoïdes, procédé de préparation de ces capsules et composition cosmétique les contenant WO2009093812A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2010540575A JP5745856B2 (ja) 2007-12-27 2008-12-24 カロチノイドを安定化した二重層構造の高分子カプセル、その製造方法及びこれを含有する化粧料組成物
CN2008801233158A CN101910256B (zh) 2007-12-27 2008-12-24 用于稳定类胡萝卜素的双层聚合物胶囊及其制备方法以及含有该聚合物胶囊的化妆品组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020070138061A KR101415994B1 (ko) 2007-12-27 2007-12-27 카로티노이드를 안정화한 이중층 구조의 고분자 캡슐, 그 제조 방법 및 이를 함유하는 화장료 조성물
KR10-2007-0138061 2007-12-27

Publications (2)

Publication Number Publication Date
WO2009093812A2 true WO2009093812A2 (fr) 2009-07-30
WO2009093812A3 WO2009093812A3 (fr) 2009-10-15

Family

ID=40901523

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2008/007645 WO2009093812A2 (fr) 2007-12-27 2008-12-24 Capsules de polymère double couche pour la stabilisation de caroténoïdes, procédé de préparation de ces capsules et composition cosmétique les contenant

Country Status (4)

Country Link
JP (1) JP5745856B2 (fr)
KR (1) KR101415994B1 (fr)
CN (1) CN101910256B (fr)
WO (1) WO2009093812A2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012138710A3 (fr) * 2011-04-07 2013-01-10 The Procter & Gamble Company Compositions d'hygiène personnelle à dépôt accru de microcapsules de polyacrylate
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130011469A1 (en) 2009-07-23 2013-01-10 U.S. Nutraceuticals, Llc D/B/A Valensa International Krill oil and carotenoid composition, associated method and delivery system
US20130295171A1 (en) 2009-07-23 2013-11-07 U.S NUTRACEUTICALS, LLC d/b/a Valensa International Krill oil and reacted astaxanthin composition and associated method
DE212013000066U1 (de) * 2012-07-19 2014-09-25 U.S. Nutraceuticals Llc Dba Valensa International Krillöl und reagierte Astaxanthinzusammensetzung
KR101342958B1 (ko) * 2013-08-08 2013-12-18 (주)바이오제닉스 수난용성 물질을 이용한 안정한 삼중층 캡슐, 이의 제조방법 및 이를 이용한 화장품 조성물
JP2017088557A (ja) * 2015-11-12 2017-05-25 富士フイルム株式会社 カプセル入り化粧料
KR102048201B1 (ko) 2017-12-29 2019-11-25 한남대학교 산학협력단 천연색소를 포함하는 나노캡슐 및 이의 제조방법
KR102151419B1 (ko) * 2018-12-28 2020-09-03 한국세라믹기술원 고효율 담지 기능 및 방출 제어 기능을 갖는 유무기 복합 소재의 제조방법
KR20240040181A (ko) 2022-09-20 2024-03-28 한남대학교 산학협력단 홍국적색소를 포함하는 나노캡슐 분산액 조성물 및 이의 제조방법
KR20240057927A (ko) 2022-10-25 2024-05-03 한남대학교 산학협력단 비트레드를 이용한 나노캡슐 분산체의 안정화 연구
KR20240057929A (ko) 2022-10-25 2024-05-03 한남대학교 산학협력단 수용성 파프리카 색소를 이용한 나노캡슐 분산체의 안정화 연구

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003503433A (ja) * 1999-07-02 2003-01-28 コグニス・イベリア・ソシエダッド・リミターダ マイクロカプセル−ｉ
US20050048008A1 (en) * 2003-08-29 2005-03-03 Bioderm Research Antiaging Cosmetic Delivery Systems
KR20070042298A (ko) * 2005-10-18 2007-04-23 (주)아모레퍼시픽 유용성 활성물질 안정화 양이온성 고분자 나노캡슐 및 이의제조방법, 및 이를 함유하는 화장료 조성물
WO2007048645A2 (fr) * 2005-10-24 2007-05-03 Ciba Holding Inc. Protection d'agents oxydables

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE29924358U1 (de) * 1998-03-19 2003-01-02 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 80539 München Nano- und Mikrokapseln mit einer Polyelektrolythülle aus mehreren Polyelektrolytschichten
ATE228883T1 (de) * 1998-03-19 2002-12-15 Max Planck Gesellschaft Herstellung von mit mehrlagen gestrichenen partikeln und hohlen schalen durch elektrostatische selbstorganisierung von nanokompositmehrlagen auf zersetzbaren schablonen
FR2787729B1 (fr) * 1998-12-29 2001-01-26 Oreal Nanocapsules a base de polymeres anioniques hydrodispersibles, leur procede de preparation et compositions cosmetiques ou dermatologiques les contenant
DE10001172A1 (de) * 2000-01-13 2001-07-26 Max Planck Gesellschaft Templatieren von Feststoffpartikeln mit Polymermultischichten
US6663900B2 (en) * 2002-02-01 2003-12-16 Kemin Foods, Lc Microcapsules having high carotenoid content
JP2005075817A (ja) * 2003-09-03 2005-03-24 Fuji Chem Ind Co Ltd Ｏ／ｗ型エマルジョン及びその製法、並びにそれからなる皮膚外用剤
US20080031909A1 (en) * 2004-12-10 2008-02-07 Dsm Ip Assets B.V. Encapsulated Cosmetic Materials
CN1928098A (zh) * 2005-09-06 2007-03-14 童志清 一种精制番茄红素的方法
WO2007046632A1 (fr) * 2005-10-18 2007-04-26 Amorepacific Corporation Nanoparticules de polymere cationique encapsulant des substances actives et composition cosmetique les contenant
JP2009084224A (ja) * 2007-09-28 2009-04-23 Fujifilm Corp マイクロカプセル及びその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003503433A (ja) * 1999-07-02 2003-01-28 コグニス・イベリア・ソシエダッド・リミターダ マイクロカプセル−ｉ
US20050048008A1 (en) * 2003-08-29 2005-03-03 Bioderm Research Antiaging Cosmetic Delivery Systems
KR20070042298A (ko) * 2005-10-18 2007-04-23 (주)아모레퍼시픽 유용성 활성물질 안정화 양이온성 고분자 나노캡슐 및 이의제조방법, 및 이를 함유하는 화장료 조성물
WO2007048645A2 (fr) * 2005-10-24 2007-05-03 Ciba Holding Inc. Protection d'agents oxydables

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
US11096875B2 (en) 2010-04-28 2021-08-24 The Procter & Gamble Company Delivery particle
WO2012138710A3 (fr) * 2011-04-07 2013-01-10 The Procter & Gamble Company Compositions d'hygiène personnelle à dépôt accru de microcapsules de polyacrylate
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
US9561169B2 (en) 2011-04-07 2017-02-07 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US10143632B2 (en) 2011-04-07 2018-12-04 The Procter And Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules

Also Published As

Publication number Publication date
JP2011507950A (ja) 2011-03-10
CN101910256B (zh) 2012-09-05
KR20090070161A (ko) 2009-07-01
WO2009093812A3 (fr) 2009-10-15
CN101910256A (zh) 2010-12-08
KR101415994B1 (ko) 2014-07-08
JP5745856B2 (ja) 2015-07-08

Similar Documents

Publication Publication Date Title
WO2009093812A2 (fr) Capsules de polymère double couche pour la stabilisation de caroténoïdes, procédé de préparation de ces capsules et composition cosmétique les contenant
JP4326026B2 (ja) 結晶性ポリマーの水分散体および使用
JP4374172B2 (ja) サーモトロピック液晶高分子マイクロカプセル及びこの製造方法、並びにこのマイクロカプセルを含有する化粧料組成物
ES2600856T3 (es) Partículas cristalinas orgánicas en bloque recubiertas con micelas
JP7110226B2 (ja) 保持特性が改善されたカプセルを製造する方法、およびその方法から得られるカプセル
JP5075860B2 (ja) 樹脂粒子、その製造方法及びその用途
CN114073644B (zh) 含有胶囊的化妆料组合物
EP2276797B1 (fr) Colorants à base de polymères encapsulés par séchage par pulvérisation
WO2007046632A1 (fr) Nanoparticules de polymere cationique encapsulant des substances actives et composition cosmetique les contenant
KR101272741B1 (ko) 유용성 활성물질 안정화 양이온성 고분자 나노캡슐 및 이의제조방법, 및 이를 함유하는 화장료 조성물
JP4091917B2 (ja) 両親媒性ジブロック共重合体及び疎水性化合物を含むベシクル
KR101262261B1 (ko) 수분산성 고분자 나노캡슐 및 이의 제조 방법, 및 이를함유하는 피부외용제 조성물
KR102076003B1 (ko) 양친매성 이방성 분체를 포함하는 이중 연속상 유화 조성물
TW201729789A (zh) 包括無機uv阻斷劑之乳化型化妝品組成物及其製備方法
EP3241542B1 (fr) Composition de co-émulsification contenant diverses tailles de particule d'émulsification, et son procédé de préparation
KR20180119499A (ko) 유화 입자 클러스터를 포함하는 수중유형 유화 조성물 및 그 제조방법
KR102645441B1 (ko) 양친매성 이방성 분체를 포함하며 안정도가 향상된 유화 조성물
KR20030077260A (ko) Ｌ-아스코빌산 함유 다중공 고분자 마이크로캡슐, 이의제조방법 및 이를 함유하는 화장료 조성물
KR101062142B1 (ko) 향상된 입자 분산성 및 점도 안정성을 가지는 알칼리 팽윤성 에멀젼 조성물
EP4389276A1 (fr) Procédé de fabrication de microcapsules comprenant un noyau polymérisé et son utilisation
TWI751991B (zh) 包括極性有機溶劑之乳化型化妝品組成物及其製備方法
TW201726105A (zh) 包括顏料粉末之乳化型化妝品組成物及其製備方法
TWI747855B (zh) 包括光干涉顏料之乳化型化妝品組成物及其製備方法
TWI731900B (zh) 包括固態脂之乳化型化妝品組成物及其製備方法
Christmann Synthesis of functional amphiphilic block copolymers as stabilizer for various nanocarriers and further surface functionalization to change protein interactions

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200880123315.8

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08871606

Country of ref document: EP

Kind code of ref document: A2

WWE Wipo information: entry into national phase

Ref document number: 2010540575

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08871606

Country of ref document: EP

Kind code of ref document: A2