WO2020222411A1 - Composé et composition cosmétique pour un agent bloquant le proche infrarouge comprenant celui-ci - Google Patents

Composé et composition cosmétique pour un agent bloquant le proche infrarouge comprenant celui-ci Download PDF

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Publication number
WO2020222411A1
WO2020222411A1 PCT/KR2020/002622 KR2020002622W WO2020222411A1 WO 2020222411 A1 WO2020222411 A1 WO 2020222411A1 KR 2020002622 W KR2020002622 W KR 2020002622W WO 2020222411 A1 WO2020222411 A1 WO 2020222411A1
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group
composition
formula
substituted
unsubstituted
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PCT/KR2020/002622
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English (en)
Korean (ko)
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오희묵
이지현
김수지
이준배
박명삼
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코스맥스(주)
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    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/0245—Specific shapes or structures not provided for by any of the groups of A61K8/0241
    • 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
    • A61K8/0295—Liquid crystals
    • 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
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/26—Optical properties

Definitions

  • It relates to a compound and a cosmetic composition for a near-infrared blocking agent thereof.
  • NIR near-infrared
  • Near-infrared rays promote the formation of skin wrinkles by a mechanism different from that of skin wrinkles generated by ultraviolet rays. Therefore, the currently used sunscreen alone cannot effectively block skin wrinkles.
  • the mechanism of skin wrinkles caused by near infrared rays is as follows.
  • Near-infrared rays have the ability to penetrate the epidermis, dermis and subcutaneous tissues of the skin. Thermal energy induced by infrared radiation transmitted to the skin layer promotes the expression of dermal fibroblasts and matrix metalloproteinases (MMPs) in the skin layer. MMPs exist in the dermis and are enzymes that degrade matrix proteins that support the strength and shape of the skin, causing the denaturation of matrix proteins (such as collagen). For this reason, when near-infrared rays penetrate the skin, skin wrinkles and skin aging may occur.
  • MMPs matrix metalloproteinases
  • Titanium dioxide is mainly used as a material for blocking near-infrared rays, but due to the nature of the material, a white clouding phenomenon occurs. This lowers the consumer's desire to purchase. In addition, since it has a photocatalytic property, there is a concern of inducing inflammation in the body when it penetrates the dermal layer or when inhaled through a respiratory system.
  • the pitch of the cholesteric liquid crystal can be freely adjusted according to the composition of the mixture to block near infrared rays of a wide range of wavelengths, and between inorganic powders of metal oxides such as titanium dioxide, which is an existing near infrared ray blocking material. It is to provide a composition that does not cause a clouding phenomenon caused by aggregation.
  • X represents a halogen group
  • Y represents an ester group or a moiety including a carbonate group
  • a particle comprising the composition is provided.
  • a cosmetic composition for a near-infrared blocker comprising the composition.
  • the composition comprising the compounds of Formula 1 and Formula according to an embodiment is transparent by selectively reflecting near infrared rays, and the pitch of the cholesteric liquid crystal can be freely adjusted according to the composition of the mixture, thereby blocking near infrared rays of a wide range of wavelengths.
  • Cloudiness caused by aggregation between inorganic powders of metal oxides such as titanium dioxide, an existing near-infrared ray blocking material does not occur, and the possibility of skin oxidation due to the photocatalytic phenomenon of titanium dioxide, an existing material, can be prevented.
  • the possibility of accumulation of metal oxides in the body due to inhalation of titanium dioxide micro and nano particles in the lungs can also be prevented.
  • FIG. 1 is a polarization microscope photograph showing that a liquid crystal composition according to an embodiment of the present invention is a cholesteric phase.
  • FIG. 2 is a diagram showing a structure of a cholesteric liquid crystal phase according to an embodiment of the present invention.
  • FIG. 3 is a diagram showing a reflection wavelength according to a cholesteric liquid crystal pitch.
  • FIG. 6 is a graph showing reflectance of a liquid crystal composition in a near infrared region according to an exemplary embodiment.
  • FIG. 7 is an image of microcapsules observed with a polarization microscope according to an embodiment of the present invention.
  • a composition according to one aspect comprises Formula 1 and Formula 2:
  • X represents a halogen group
  • Y represents a moiety including an ester group or a carbonate group
  • R and R' are each independently a substituted or unsubstituted C 1 -C 60 alkyl group Show.
  • X may be Cl, Br or I.
  • X is Cl.
  • R 1 and R 2 is each independently a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group and substituted or It may be selected from unsubstituted C 1 -C 10 heterocycloalkenyl groups.
  • Y may be an organic radical or organic radicals
  • R and R'in Formulas 1 and 2 may be represented by Formula 2a:
  • * represents a bond with a neighboring atom.
  • R 1 may be represented by the following Formula 3a
  • R 2 may be represented by the following Formula 3b:
  • * represents a bond with a neighboring atom.
  • R 2 represents Cl
  • R represents the following Formula 2a
  • R'in Formula 2 represents the following Formula 2a
  • R 2 can be represented by the following formula 3b:
  • the composition may include 20 to 40% by weight of the compound of Formula 1, and 60 to 80% by weight of the compound of Formula 2.
  • the composition includes 30 to 35% by weight of the compound of Formula 1, and 65 to 70% by weight of the compound of Formula 2.
  • the weight% ratio of the compound of Formula 1 and the compound of Formula 2 may be 1:1 to 1:4.
  • the weight percent ratio of the compound of formula 1 and the compound of formula 2 is 1:1 to 1:3.
  • the composition may be a composition having cholesteric liquid crystal properties.
  • Having a cholesteric liquid crystal property means that when the liquid crystal molecules are in a cholesteric phase, a twist is added to the molecules oriented in a certain direction to form a spiral shape in a direction perpendicular to the layer as a whole. This is schematically shown in FIG. 2.
  • FIG. 3 is a diagram showing a reflection wavelength according to a cholesteric liquid crystal pitch.
  • n e is the ideal refractive index, and n o is the normal refractive index.
  • the liquid crystal molecules When light enters the liquid crystal molecules, it has a different refractive index depending on the polarization direction, so the speed of progress changes. For example, if the refractive index of a specific liquid crystal molecule in the direction of the long axis of the molecule is large (ideal refractive index, n e ), and the refractive index in the direction perpendicular to the long axis of the molecule is small (normal refractive index, n o ), the light incident on the molecule is the long axis The light in the polarization direction horizontal to and horizontal will be delayed, and the light in the polarization direction perpendicular to the long axis will have little delay.
  • n e ideal refractive index
  • n o normal refractive index
  • the refractive index is (speed of light in vacuum) ⁇ (speed of light in medium). For this reason, birefringence of light occurs. If such birefringence occurs in the cholesteric phase of the liquid crystal, light having a wavelength corresponding to the equation of ⁇ is n ⁇ P is continuously phase delayed along the helical structure of the liquid crystal.
  • the cholesteric liquid crystal has a left-handed helical structure
  • light incident on the left circularly polarized light is reflected, and light incident on the right circularly polarized light passes through the liquid crystal as it is.
  • the wavelength of light conforming to the above principle varies according to the pitch of the cholesteric liquid crystal, the wavelength of light to be reflected can be selected by adjusting the pitch.
  • the average refractive index (n) may also change according to the composition of the liquid crystal mixture.
  • the area of the reflection wavelength which is the product of the refractive index and the liquid crystal pitch, is in the near-infrared area. Accordingly, it may have a characteristic of reflecting near infrared rays.
  • the refractive index of the composition having cholesteric liquid crystal properties may be 1.1 to 1.9 at 25°C to 40°C, and a liquid crystal pitch may be 400 to 600 nm.
  • the wavelength range reflected by the composition may be specifically 700 to 1800 nm.
  • the wavelength range that the composition reflects is 700 to 1100 nm.
  • Microcapsules according to another aspect may contain the composition.
  • the microcapsules can be manufactured by a generally known method, and for detailed manufacturing methods, see Examples.
  • the microcapsules may be lipozoohms.
  • the cosmetic composition for a near-infrared blocker comprising according to another aspect may include the composition.
  • the composition may be present in particles (eg, microcapsules).
  • the cosmetic composition for the near-infrared blocking agent may include particles (eg, microcapsules), and the particles (eg, microcapsules) may include a composition including compounds of Formulas 1 and 2.
  • the cosmetic composition for the near-infrared ray blocking agent is generally used in cosmetics in addition to particles (eg, microcapsules) containing the compounds of Formulas 1 and 2, carriers containing at least one oil phase, covalent agents, fats and waxes , Stabilizers, thickeners, biologically active ingredients, film-forming agents, fragrances, colorants, pearlescent agents, preservatives, pigments, electrolytes (eg, magnesium sulfate), pH adjusters, antioxidants, surfactants, etc. , But is not limited thereto.
  • the C 1 -C 60 alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl group, ethyl group, propyl group, isobutyl group, sec-butyl Group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, and the like.
  • a C 1 -C 60 alkylene group refers to a divalent group having the same structure as the C 1 -C 60 alkyl group.
  • the C 2 -C 60 alkenyl group refers to a hydrocarbon group including one or more carbon double bonds in the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include ethenyl group, propenyl group, butenyl group And the like.
  • the C 2 -C 60 alkenylene group refers to a divalent group having the same structure as the C 2 -C 60 alkenyl group.
  • the C 2 -C 60 alkynyl group refers to a hydrocarbon group including one or more carbon triple bonds in the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like. Included.
  • the C 2 -C 60 alkynylene group refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
  • the C 1 -C 60 alkoxy group refers to a monovalent group having the formula of -OA 101 (here, A 101 is the C 1 -C 60 alkyl group), and specific examples thereof include a methoxy group, an ethoxy group And an isopropyloxy group.
  • the C 3 -C 10 cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclo And heptyl group.
  • a C 3 -C 10 cycloalkylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.
  • the C 1 -C 10 heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, and , Specific examples thereof include 1,2,3,4-oxatriazolidinyl group (1,2,3,4-oxatriazolidinyl), tetrahydrofuranyl, tetrahydrothiophenyl group, and the like.
  • the C 1 -C 10 heterocycloalkylene group refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkyl group.
  • the C 3 -C 10 cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in the ring, but not having aromaticity. Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like.
  • the C 3 -C 10 cycloalkenylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkenyl group.
  • the C 1 -C 10 heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, and Has at least one double bond within.
  • Specific examples of the C 1 -C 10 heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, and 2,3-dihydro And a thiophenyl group.
  • the C 1 -C 10 heterocycloalkenylene group refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkenyl group.
  • a substituted C 1 -C 60 alkyl group, a substituted C 2 -C 60 alkenyl group, a substituted C 2 -C 60 alkynyl group, a substituted C 1 -C 60 alkoxy group, a substituted C 3 -C 10 At least one of the substituents of a cycloalkyl group, a substituted C 1 -C 10 heterocycloalkyl group, a substituted C 3 -C 10 cycloalkenyl group, and a substituted C 1 -C 10 heterocycloalkenyl group,
  • Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 cycloalkyl group, C 1 -C 10 hetero cycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heteroaryl cycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy, C 6 -C 60 aryl come T, C 1 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C( O)(Q 11 ), -S(
  • the Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, ami Dino group, hydrazino group, hydrazono group, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 1 -C 60 heteroaryl group, monovalent non-aromatic A condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a C 1 -C 60 alky
  • * and *' mean a bonding site with a neighboring atom in the corresponding formula.
  • Particles according to another aspect include a composition comprising the compounds of Formula 1 and Formula 2.
  • the composition including the compounds of Formulas 1 and 2 may be encapsulated in particles.
  • the particles may be microcapsules.
  • the particles may be a biodegradable polymer.
  • the biodegradable polymer are polystyrene (polystyrene), polymethyl methacrylate (PMMA), polyethylene terephthalate (PET), polyvinyl chloride (PVC), polyethylene (PE), polypropylene (PP), polytetrafluoro Ethylene (PTFE), aliphatic polyester polymer, poly(L-lactic acid) (PLLA), poly(D,L-lactic acid) (PDLLA), poly(glycolic acid) (PGA), poly(caprolactone) (PCL) ), poly(hydroxyalkanoate), polydioxanone (PDS), polytrimethylene carbonate, or a copolymer of these units poly(lactic acid-co-glycolic acid) (PLGA), poly(L -Lactic acid-co-caprolactone) (PLCL), poly(glycolic acid-co-caprolactone) (PGCL), derivatives thereof, and
  • a cosmetic composition comprising the compounds of Formulas 1 and 2, or a skin external preparation or cosmetic composition comprising the particles (eg, microparticles).
  • the composition comprising the compounds of Formula 1 and Formula 2 has a near-infrared blocking effect, and may be usefully used in the external preparation for skin or cosmetic composition. Therefore, the skin external preparation or cosmetic composition may be a near-infrared blocking skin external preparation or a cosmetic composition.
  • the cosmetic composition of the present invention may be formulated as, for example, a liquid product, lotion, essence, cream, sun lotion, sun cream, makeup base, foundation, BB cream, stick-shaped product, or balm type product, etc. It is not limited thereto.
  • oil, water, surfactants, moisturizers, lower alcohols, thickeners, chelating agents, preservatives, fragrances, etc. may be additionally selected and added according to the formulation to be prepared.
  • a sunscreen agent, a light scattering agent, and the like may be included, and the formulation and additive components thereof are not limited to the above contents.
  • the above ingredients may be introduced in amounts generally used in the field of dermatology.
  • the cosmetic composition includes additional ingredients commonly used in cosmetics, such as thickeners, dispersants, flavors, fillers, preservatives, preservatives, neutralizing agents, sweeteners, vitamins, free-radical scavengers, metal ion sequestering agents, functional ingredients, and these Any conventional cosmetic ingredients that may be selected from mixtures of may further be included.
  • the external preparation for skin may be a cream, gel, ointment, skin emulsifier, skin suspension, transdermal delivery patch, drug-containing bandage, lotion, or a combination thereof.
  • the external preparation for skin may be prepared and used in the form of an ointment, lotion, spray, patch, cream, powder, suspension, gel or gel.
  • the above skin external preparations are ingredients commonly used in external preparations for skin such as cosmetics and pharmaceuticals, such as aqueous ingredients, oily ingredients, powder ingredients, alcohols, moisturizers, thickeners, ultraviolet absorbers, whitening agents, preservatives, antioxidants, surfactants, fragrances. , Colorants, various skin nutrients, or combinations thereof and may be appropriately formulated according to need.
  • the external preparations for skin include metal sequestering agents such as disodium edetate, trisodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, and gluconic acid, caffeine, tannin, bellapamil, licorice extract, glavidine, and caline.
  • Hot water extract of fruit, various herbal medicines, drugs such as tocopherol acetate, glytilithic acid, tranexamic acid and derivatives or salts thereof, vitamin C, magnesium ascorbate, glucoside ascorbic acid, arbutin, kojic acid, glucose, fructose, Sugars such as trehalose can also be appropriately blended.
  • a method for blocking near-infrared rays of an individual comprising the step of applying a composition comprising the compounds of Formula 1 and Formula 2, particles comprising the same, or a skin external preparation or cosmetic composition comprising the same to the skin. .
  • composition is the same as described above.
  • the subject may be a mammal, for example a human, cow, horse, pig, dog, sheep, goat, or cat.
  • a cholesteric liquid crystal compound of the following compounds CC (Cholesteryl chloride, Sigma-Aldrich) and COC (Cholesteryl oleyl carbonate, Sigma-Aldrich) was prepared.
  • a composition was prepared by mixing CC and COC in the ratio shown in Table 1.
  • CC and COC were put in the same container at the weight% ratio of Table 1 Heat above the phase transition temperature to become a phosphorus liquid. After that, it is sufficiently stirred so that CC and COC are homogeneously mixed.
  • FIG. 1 is a photograph of an orientation structure of a liquid crystal composition according to an embodiment of the present invention observed with a polarization microscope.
  • the characteristic polarization image texture shown in FIG. 1 is Example 3 Indicates that the composition of is in the cholesteric phase at that temperature.
  • a typical temperature range of room temperature or body temperature is 25°C to 36.5°C.
  • the phase transition temperature which is the temperature at which the cholesteric phase becomes an isotropic liquid, is preferably higher than 25°C.
  • the phase transition temperature from the isotropic liquid to the cholesteric phase is preferably higher than 25°C.
  • phase transition temperature of the compositions of Examples 1, 2, and 3 is higher than 25°C. If it has an appropriate composition ratio, it is possible to reflect near-infrared rays in a desired temperature range.
  • FIG. 4 is a graph showing a change in a central reflection wavelength versus temperature according to a mixture composition of Formulas 1 and 2 according to an embodiment of the present invention
  • FIG. 6 is a graph showing a reflectance according to a wavelength of a liquid crystal composition according to an embodiment of the present invention. to be.
  • the range of the reflection wavelength varies depending on the mixing composition ratio of the compounds of Formula 1 and Formula 2 according to an embodiment of the present invention.
  • composition was stirred at 38° C. and 300 rpm for 10 hours to evaporate DCM and then cooled to room temperature.
  • composition was washed with distilled water and decanting was repeated 3 times to obtain microcapsules.
  • FIG. 7 is an image of microcapsules observed with a polarization microscope according to an embodiment of the present invention. Referring to FIG. 7, it can be seen that a bright shape is confirmed due to the liquid crystal in the microcapsules in the polarized picture. This means that the liquid crystal composition is properly encapsulated in the microcapsules.
  • Cosmetics prepared in this way may also have an effect of blocking near-infrared rays due to the liquid crystal contained in the microcapsules.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

L'invention concerne : une composition comprenant des composés de formules chimiques 1 et 2; des particules les comprenant; et une composition cosmétique pour un agent bloquant le proche infrarouge.
PCT/KR2020/002622 2019-04-30 2020-02-24 Composé et composition cosmétique pour un agent bloquant le proche infrarouge comprenant celui-ci WO2020222411A1 (fr)

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WO2009079546A1 (fr) * 2007-12-19 2009-06-25 Avon Products, Inc. Compositions colorantes à base de cristaux liquides cholestériques et articles produits correspondants
KR20150062261A (ko) * 2013-11-28 2015-06-08 주식회사 진영바이오 콜레스테롤 유도체 기반의 리퀴드크리스탈 및 이를 함유한 리퀴드크리스탈 캡슐
KR20170138930A (ko) * 2016-06-08 2017-12-18 주식회사 엘지생활건강 콜레스테릭 액정 입자를 포함하는 화장료 조성물 및 그의 제조방법
KR20180053458A (ko) * 2016-11-11 2018-05-23 주식회사 케이피티 콜레스테릭 액정 캡슐 제조방법 및 이를 포함하는 화장료 조성물

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DE102012017854A1 (de) 2012-09-08 2014-05-28 Kronos International, Inc. Infrarot-reflektierendes Pigment auf Basis Titandioxid sowie Verfahren zu seiner Herstellung
KR20140095736A (ko) 2013-01-25 2014-08-04 주식회사 엘지생활건강 근적외선 차단용 복합분체
WO2016171383A1 (fr) 2015-04-22 2016-10-27 코스맥스 주식회사 Procédé d'évaluation d'efficacité de matériau de blocage des rayons infrarouges

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2681143B2 (ja) * 1988-03-24 1997-11-26 ポーラ化成工業株式会社 コレステリック液晶組成物及びこれを含有してなる化粧料
WO2009079546A1 (fr) * 2007-12-19 2009-06-25 Avon Products, Inc. Compositions colorantes à base de cristaux liquides cholestériques et articles produits correspondants
KR20150062261A (ko) * 2013-11-28 2015-06-08 주식회사 진영바이오 콜레스테롤 유도체 기반의 리퀴드크리스탈 및 이를 함유한 리퀴드크리스탈 캡슐
KR20170138930A (ko) * 2016-06-08 2017-12-18 주식회사 엘지생활건강 콜레스테릭 액정 입자를 포함하는 화장료 조성물 및 그의 제조방법
KR20180053458A (ko) * 2016-11-11 2018-05-23 주식회사 케이피티 콜레스테릭 액정 캡슐 제조방법 및 이를 포함하는 화장료 조성물

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