WO2017088146A1 - Composition comprenant des microcapsules - Google Patents

Composition comprenant des microcapsules Download PDF

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Publication number
WO2017088146A1
WO2017088146A1 PCT/CN2015/095675 CN2015095675W WO2017088146A1 WO 2017088146 A1 WO2017088146 A1 WO 2017088146A1 CN 2015095675 W CN2015095675 W CN 2015095675W WO 2017088146 A1 WO2017088146 A1 WO 2017088146A1
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Prior art keywords
composition
weight
mixture
core
microcapsules
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PCT/CN2015/095675
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English (en)
Inventor
Ruijun Chen
Liang Zhang
Junrong ZHAO
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L'oreal
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Priority to PCT/CN2015/095675 priority Critical patent/WO2017088146A1/fr
Publication of WO2017088146A1 publication Critical patent/WO2017088146A1/fr

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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
    • A61K8/02—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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • 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
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • 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
    • A61K2800/65—Characterized by the composition of the particulate/core
    • A61K2800/651—The particulate/core comprising inorganic material

Definitions

  • the present invention relates to the field of compositions for treating keratin materials, and especially to the field of compositions which comprises releasable colorant (s) , and with a UV-screening effect.
  • Whitening and brightening of the skin is always high interests of the consumers, especially those who have a dark or dull skin tone.
  • Cosmetic compositions are used to meet the expectations of the consumers, from many different aspects, such as an instant aesthetic color and coverage of skin imperfections, long term whitening or brightening of the skin tone, and anti UV radiation. Many formulations have been developed to date to achieve one or all of these aspects.
  • Instant color and coverage of the skin imperfection can be achieved by including in cosmetic composition microencapsulated colorants wherein, upon application on the skin, the composition provides the expected changing color. More particularly, the change of color is provided by the colorant-containing microcapsules, which upon rupture by application of a mechanical force, releasing the entrapped colorant into the composition, thereby changing its color. A mechanical action such as rubbing spread the topical composition and facilitates its penetration into the skin. The immediate change of color of the composition provides a visual esthetical effect.
  • Hydroxylated diphenylmethane derivatives are known from application WO2004/105736 in compositions in emulsion form for that purpose.
  • UV filters of various types for preventing the skin from the harm of both UV-B rays (with a wavelengths of between 280 and 320 nm) and UV-A rays (with a wavelength of between 320 and 400 nm) .
  • PCT/CN2012/070490 disclosed a color changing composition for caring for and/or making up keratin materials, comprising microcapsules containing releasable colorants, a swelling agent, and at least one UV filter. More preferably, it was disclosed that resorcinol and its derivatives may be formulated in the above mentioned composition.
  • the present invention aims at providing a stable composition for treating keratin materials, with an instant aesthetic color and coverage of skin imperfections, long term whitening or brightening of the skin tone, and full range anti UV radiation.
  • compositions for treating keratin materials comprising a combination of color-changing microcapsules, hydroxylated diphenylmethane derivative (s) , and specific UV screening agents.
  • Another aspect of the present invention is a method for treating keratin materials, comprising the step of applying the composition of the present invention to the keratin materials.
  • the invention relates to a composition for treating a keratin material, comprising:
  • R1 is chosen from a hydrogen atom, a methyl group, a saturated or unsaturated, linear or branched alkyl chain having from 2 to 4 carbon atoms, an-OH group, and a halogen,
  • R2 is chosen from a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched alkyl chain having from 2 to 5 carbon atoms,
  • R3 is chosen from a methyl group or a saturated or unsaturated linear or branched alkyl chain having from 2 to 5 carbon atoms,
  • R4 and R5 are, independently of each other, chosen from a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched alkyl chain having from 2 to 5 carbon atoms, an-OH group or a halogen;
  • At least one combined UV-A and UV-B screening agent chosen from the group consisting of benzophenone compounds, optionally amino-substituted, phenyl benzotriazole compounds, or a mixture thereof.
  • full range anti UV radiation effect it is in particular meant both the SPF (Sun Protection Factor) and PPD (Persistent Pigment Darkening) value of a composition are both present when the UV-A screening agent is present in the composition comparatively to substantially the same composition without it.
  • SPF is preferably measured according to International standard EN ISO 24444: 2010 Cosmetics-Sun protection test methods-In vivo determination of the sun protection factor (SPF) .
  • PPD skin darkening that persists more than 2 h after the end of UVA exposure. It is determined according to ISO 24442: 2011 (en) Cosmetics-Sun protection test methods-In vivo determination of sunscreen UVA protection.
  • stable means that the composition after two months of storage at 4°C, room temperature (25°C) and 45°C, shows no change in appearance, colour, odour, or viscosity.
  • keratin material means the skin (of the body, face and around the eyes, scalp) , nails, lips or mucous membranes. In particular, it refers to the skin.
  • Figure 1 is a schematic diagram illustrating a typical structure of color-changing microcapsule of the present invention, wherein A represent a coloured core, B, C, D and E being different layers concentrically surrounding said core A, at least one of these surrounding layers being mandatory including preferably titanium dioxide particles, the others being optional.
  • Figures 2 represent a schematic diagram showing the core-shell structure of color-changing microcapsules comprising 3 layers: coloured core –inner color layer–TiO 2 particles layer.
  • Figures 3 represent a schematic diagram showing the core-shell structure of color-changing microcapsules comprising 2 layers: coloured core–TiO 2 particles layer.
  • composition of the present invention comprises at least one hydroxylated diphenylmethane derivatives of the formula (I) ,
  • R1 is chosen from a hydrogen atom, a methyl group, a saturated or unsaturated, linear or branched alkyl chain having from 2 to 4 carbon atoms, an-OH group, and a halogen,
  • R2 is chosen from a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched alkyl chain having from 2 to 5 carbon atoms,
  • R3 is chosen from a methyl group or a saturated or unsaturated linear or branched alkyl chain having from 2 to 5 carbon atoms,
  • R4 and R5 are, independently of each other, chosen from a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched alkyl chain having from 2 to 5 carbon atoms, an-OH group or a halogen.
  • The-OH, R1, R4 and R5 groups may be at the ortho, meta or para position with respect to the bond formed with the carbon linking the two aromatic rings to each other.
  • R1, R2, R4 and R5 denote a hydrogen atom
  • R3 is a methyl group
  • the-OH groups are at the ortho and para positions with respect to the bond formed with the carbon linking the two aromatic rings to each other.
  • Such a compound is marketed under the name SYMWHITE or BIO 377 by the company SYMRISE.
  • composition according to the invention comprises (a) at least one hydroxylated diphenylmethane derivative of formula (II) .
  • the hydroxylated diphenylmethane derivatives of formula (I) is present in amount from 0.01%to 5%by weight, preferably from 0.05%to 3%by weight, more preferably from 0.1%to 1%by weight, relative to the total weight of the composition.
  • microcapsule refers to a spherical microcapsule containing at least one layered coating entrapping at least one colorant and surrounding a core chemically different from the coating. Microcapsules are distinct from microspheres, which consist of spherical homogeneous matrix.
  • the “at least one layered coating” is a multi-layered coating.
  • multi-layer microcapsule refers to a microcapsule consisting of an inner core (or core seed) surrounded by a coating based on one or more inner layer (s) and one outer layer.
  • the one or more inner layer (s) forming the multi-layer coating of the multi-layer microcapsule and the single layer of the outer core microcapsule may be formed of the same or different compound (s) .
  • the color-changing microcapsules introduced in the composition according to the invention contain releasable colorant (s) and have a high durability during storage and handling and a high masking ability of inner color, has a high loading amount of colorant in a particle, can be easily ruptured by pressing, rubbing, wiping and/or scrubbing with hand or an implement such as cloths, sponge or paper to reveal or develop the color on the inner color layer as well as can maintain a long period stability.
  • s releasable colorant
  • microcapsules are deformable in the composition.
  • microcapsules inside the composition are breakable under pressure at the application on the keratin materials.
  • Said microcapsules are obtainable, and preferably obtained, with at least one step of fluidized bed process, in particular with at least one step of fluidized bed coating process.
  • the microcapsule according to the invention comprises an inner core surrounded by a coating based on one or more inner layer (s) and one outer layer.
  • the microcapsule is a ‘multi-layers’ microcapsule, comprising at least one inner layer and one outer layer.
  • the one or more inner layer (s) forming the multi-layer coating of the multi-layer microcapsule and the single layer of the outer core microcapsule may be formed of the same or different compound (s) .
  • the outer layer (s) does not comprise any colorant. In another embodiment, the outer layer (s) comprise (s) at least one colorant.
  • colorant refers to organic pigments such as synthetic or natural dyes selected from any of the well-known FD&C or D&C dyes, inorganic pigments such as metal oxides, or lakes and any combination (blend) thereof. Accordingly, the colorant useful according to the present invention may be oil-soluble or oil-dispersible or with limited solubility in water.
  • the color-changing microcapsule preferably comprises:
  • -a core including at least one coloured core and eventually at least one inner color layer (s) , and
  • -a shell having at least one pressure-breakable wall layer surrounding said core, an optional outer color layer and an optional outmost shell.
  • the microcapsules includes colorant (s) selected from inorganic pigment (s) , preferably selected from metal oxide, such as iron oxides and titanium oxide.
  • the coloured core includes at least one inorganic pigment advantageously selected from at least one metallic oxide, more advantageously selected from at least one iron oxide.
  • the pressure-breakable wall layer includes at least one inorganic pigment advantageously selected from at least one metallic oxide, more advantageously selected from at least one titanium oxide.
  • iron oxides are located at least in the coloured core and titanium oxides are located at least in a pressure-breakable wall layer surrounding said core.
  • the color-changing microcapsules according to the invention comprise at least 70%by weight of colorant (s) , preferably of inorganic pigment (s) , preferably of a mixture of inorganic pigments, preferably of metallic oxides such as iron oxides and titanium oxides, compared to the total weight of the color-changing microcapsules.
  • average particle size diameters of colorant microcapsules up to about 800 microns are used according to the invention.
  • the average particle size diameter of the colorant microcapsules is less than about 400 microns for skin care applications.
  • the average particle size diameter is in the range of about 10 to 350 microns.
  • the average particle size will be from 50 ⁇ m to 800 ⁇ m, and in particular from 60 ⁇ m to 400 ⁇ m.
  • the color-changing microcapsule according to the present invention has a mean particle size of about from 18 to 270 mesh (around from 1000 ⁇ m to 53 ⁇ m) , particularly about from 25 to 170 mesh (around from 710 ⁇ m to 90 ⁇ m) .
  • a composition according to the invention may comprise from 0.1%to 20%by weight and preferably from 0.1%to 5%by weight of microcapsules relative to the total weight of the said composition.
  • the amount of the color-changing microcapsules ranges from 0.1%to 5%by weight, preferably from 0.2%to 3%by weight relative to the total weight of composition.
  • the encapsulated colorant (s) may be present in a composition according to the invention in an amount in active matter of encapsulated pigments ranging from 0.1%to 20%by weight, in particular from 0.5%to 15%by weight, and more particularly from 0.1%to 5%by weight, of the total weight of said composition.
  • microcapsules according to the inventions are added and mixed uniformly at temperatures under 50°C. They are mixed gently with a paddle rather than a homogenizer.
  • microcapsules may be produced by several methods known from the man skilled in the art within the coating or encapsulation domain, including pelletization, granulation, coating, etc...
  • the microcapsules may be obtained by steps comprising mixture of the compounds (actives, pigments, polymers, solvents) and drying to form capsules as disclosed in WO01/35933 and WO2011/027960, or steps of granulation and coating by spray drying as disclosed in FR2841155, or by fluidized bed technology, which has been used in the food and pharmaceutical industry.
  • WO08139053 for the preparation of spheroid multilayer comprising a core of sugar and concentric layers of pharmaceutical actives. Fixation of pharmaceutical actives on the core is made by impregnation or pulverization or projection, and then the 1st layer is dried before application of a second one.
  • microcapsules introduced in the composition according to the invention are obtainable, and preferably obtained, at least in part, by fluidized bed technology which will be described later in this description.
  • the specificity of the fluid bed process is that it leads to real capsules compared to spray drying, which leads to a matrix with the core material randomly dispersed in a polymer.
  • more than 60%, preferably more than 70%, particularly more than 80%, and more particularly more than 90%of color-changing microcapsules will be ruptured to release the inner colorant within 1 minute, preferably from 1 to 40 seconds, particularly from 1 to 30 seconds, more particularly from 1 to 20 seconds after pressing, rubbing, wiping and/or scrubbing with hand or an implement.
  • said ratio and time-limit does not critical in the present invention.
  • the core of the microcapsule comprises a coloured core which comprises at least one colorant and optionally at least one binder.
  • the colorant (s) preferably includes at least one pigment, preferably selected from at least one iron oxide (s) .
  • the binder is preferably selected from at least one hydrophilic polymer, at least one lipid-based material, and their mixture, preferably their mixture.
  • the core can be prepared in a form of particle, powder, granule, micro sphere, microcapsule, for example, by spray drying or fluid bed process of the solution comprising at least one colorant, at least one polymer as a wall-forming material and at least one lipid-based material in a solvent.
  • the size of coloured core, and more generally of the core, is not particularly limited and may be suitably chosen according to the finally desired color-changing microcapsule.
  • the size of the coloured core may be larger than 20 ⁇ m or more, particularly 30 ⁇ m or more, preferably 40 ⁇ m or more, more preferably 50 ⁇ m or more, and smaller than 800 ⁇ m or less, particularly 700 ⁇ m or less, preferably 600 ⁇ m or less, more preferably 500 ⁇ m or less.
  • the radius of the core is larger than 50 %, specifically 60%, preferably 70%and more preferably 80%, based on the total radius of the microcapsule.
  • the ratio between the radius of the core and the thickness of the shell is selected from 1:0.05 to 1:0.5.
  • the content of the core is more than 30 %by weight, specifically 40%, based on the total weight of the microcapsule. Therefore, the microcapsule of the present invention has a high loading amount of colorant in a particle.
  • the core can have one or more inner color layer (s) surrounding the coloured core.
  • the inner color layer (s) may be every layers located between the coloured core and the pressure-breakable wall layer.
  • the inner color layer including, for example, first inner color layer, second inner color layer and third inner color layer, etc. , wherein the colorants and binders contained in each inner color layers are the same or different from each other.
  • the coloured core can comprise one or two inner color layers, preferably one inner color layer.
  • the coloured core can be formed by a granulation of a solution for the coloured core comprising at least one colorant and preferably at least one binder
  • an inner color layer can be formed by coating the coloured core with a solution for the inner color layer comprising at least one colorant and preferably at least one binder.
  • Said coating process can be performed by a fluidized bed coating process.
  • the thickness of an inner color layer is not particularly limited and may be suitably chosen according to the finally desired color-changing microcapsule.
  • the thickness of the coloured core, and more generally of the core may be larger than 20 ⁇ m or more, particularly 40 ⁇ m or more, preferably 60 ⁇ m or more, more preferably 80 ⁇ m or more, and smaller than 200 ⁇ m or less, particularly 160 ⁇ m or less, preferably 120 ⁇ m or less, more preferably 100 ⁇ m or less.
  • the content of an inner color layer may be from 20 to 80 %by weight, specifically from 30 to 70%by weight, preferably from 40 to 60 %by weight based on the total weight of core.
  • the coloured core does not contain a binder and is surrounded with an inner color layer comprising a colorant and a binder, by which pigments contained in the core will be more easily dispersed when the microcapsule is ruptured.
  • a binder in the coloured core, can be used in an amount that colorant will not fall apart or separate from the layer during the coating process and/or after the removal of solvent, and generally can be used in an amount selected from 1%to 30%by weight, preferably from 2%to 25%by weight, more preferably from 4%to 15%by weight in the terms of total weight of the core.
  • the colorant (s) and preferably the pigment (s) , still more preferably the iron oxide (s) , is (are) present in the core in an amount of at least 70%by weight, specifically at least 75 %by weight, preferably at least 80%by weight, more preferably at least 85%by weight, such as from 80 to 99%by weight, relative to the total weight of the relative to the total weight of the core.
  • the content of iron oxide (s) particles in the microcapsule is preferably selected from 20%to 60%by weight, preferably from 25%to 55%by weight, more preferably from 30%to 50%by weight, relative to the total weight of the microcapsule.
  • the content of iron oxide (s) particles in the microcapsule is preferably selected from 30%to 58 %by weight, preferably from 35%to 55%by weight, more preferably from 40%to 50%by weight, relative to the total weight of the microcapsule.
  • the color-changing microcapsule of the present invention has a pressure-breakable wall layer including at least one colorant.
  • Said colorant (s) is (are) preferably selected from inorganic pigment, more preferably from metallic oxide and still more preferably from titanium dioxide particle.
  • the colorant contained into the pressure-breakable wall layer is distinct from the colorant (s) contained in the coloured core, for instance being both metallic oxides distinct from each other.
  • the titanium dioxide particles are preferably are discontinuously dispersed in the layer and linked to each other by a binder.
  • pressure-breakable or “pressure-friable” means that a rupture can be easily made by pressing, rubbing, wiping and/or scrubbing with hand or an implement such as cloths, sponge or paper.
  • a pressure-breakable titanium dioxide particles layer can comprise particles of titanium dioxide and a binder, and said binder can comprise a wall-forming material.
  • the titanium dioxide particles lodged in the wall-forming materials will break the pressure-breakable wall layer in an irreversible manner and facilitate or increase the disintegration or dissolution of said wall layer. Further, it is also estimated that titanium dioxide particles do an important role for the strength, the durability, the pressure-breakability, the after-feeling of the wall layer.
  • the pressure-breakable wall layer can be formed by the following procedure:
  • Said coating may be performed by using the fluidized bed process, but other coating process can be utilized, if necessary.
  • solvents which can be utilized in the above procedure, mention can be made of water or a low boiling solvent such as methylene chloride, methanol and ethanol.
  • the titanium dioxide particle layer of which thickness can vary depending on the amount of titanium dioxide used and/or the type of binder, and may have a thickness of 10 ⁇ m or more, preferably 20 ⁇ m or more, more preferably 30 ⁇ m or more, particularly 40 ⁇ m or more, commonly 300 ⁇ m or less, preferably 250 ⁇ m or less, more preferably 200 ⁇ m or less, particularly 150 ⁇ m or less.
  • the content of titanium dioxide particles in the pressure-breakable wall layer is preferably selected from 50%to 99%by weight, preferably from 60 to 98%by weight, more preferably from 70%to 97%by weight, particularly from 80%to 95%by weight, in terms of total weight of the pressure-breakable wall layer.
  • the content of colorant (s) and in particular of titanium dioxide particles, represents less than 100%of the pressure-breakable wall layer.
  • the content of titanium dioxide particles in the microcapsule is preferably selected from 20%to 60%by weight, preferably from 25%to 55%by weight, more preferably from 30%to 50%by weight, relative to the total weight of the microcapsule.
  • the colorant (s) in the core preferably iron oxide (s)
  • the colorant (s) in the pressure-breakable wall layer preferably titanium dioxide particles
  • the iron oxide (s) and the titanium dioxide particles are both present in a respective total amount in the microcapsules such as the weight ratio of the iron oxide (s) relatively to titanium dioxide particles is greater than or equal to 1.
  • the mean diameter or size of titanium dioxide particles is not specifically limited but has a mean diameter of usually from 10 nm to 20 ⁇ m, preferably from 50nm to 10 ⁇ m, more preferably from 100nm to 5 ⁇ m, and particularly from 150nm to 5 ⁇ m.
  • the mean diameter or size of less than 10nm of titanium dioxide particles may result to a decrease in the pressure-breakable ability, and the mean diameter of more than 20 ⁇ m may make difficult the formation of titanium dioxide particles layer. Titanium dioxide particles having a first particle size of less than the above range but having a second particle size falling down the above particle size range can be applicable in the present invention.
  • the color-changing microcapsule additionally comprises an optional outer color layer onto the pressure-breakable wall layer, in particular pressure-breakable titanium dioxide particles layer.
  • the outer color layer can be formed by coating the titanium dioxide particles layer with a solution having a colorant and a binder, for example, by the fluidized bed process.
  • the colorant and binder used in the outer color layer can be the same or different from those used in the inner color layer.
  • the outer color layer is given to impart a visual color different from white color issued from the titanium dioxide particles layer and/or the color of inner color layer. Therefore, a colorant in the outer color layer can be used in an amount that does not disturb the color developed by the inner color layer when the microcapsules are scrubbed.
  • the content of an outer color layer can be selected, in terms of the total weight of core, from 1 to 60 parts per weight, preferably from 2 to 50 parts per weight, more preferably from 3 to 40 parts per weight, particularly from 4 to 30 parts per weight.
  • the content of a colorant in the outer color layer may be selected, in terms of total weight of colorants in the inner color layer, from 0.01 to 5 parts per weight, preferably from 0.05 to 4.5 parts per weight, more preferably from 0.1 to 4 parts per weight, particularly from 0.5 to 3.5 parts per weight.
  • the content of a colorant in an outer color layer may be additionally increased if the color of the outer color layer would not disturb the color of the inner color layer.
  • a person skilled in the art can choose the color and content of a colorant in an outer color layer in an appropriate manner by considering the color and content of colorants contained in inner color layers and the desired color to be finally developed.
  • the thickness of an outer color layer is not particularly limited and may be suitably chosen according to the finally desired color-changing microcapsule.
  • the out color layer may have a thickness which is larger than 20 ⁇ m, particularly 40 ⁇ m, preferably 60 ⁇ m, more preferably 80 ⁇ m, and which is smaller than 200 ⁇ m, particularly 150 ⁇ m, preferably 120 ⁇ m, more preferably 100 ⁇ m.
  • Microcapsule of the present invention can comprise a protective outmost shell onto a pressure-breakable wall layer, in particular pressure-breakable titanium dioxide particles layer or an additional outer color layer to protect the microcapsule against water in the air during storage or to ensure a long period stability of the microcapsule in a carrier, notably in solution.
  • a pressure-breakable wall layer in particular pressure-breakable titanium dioxide particles layer or an additional outer color layer to protect the microcapsule against water in the air during storage or to ensure a long period stability of the microcapsule in a carrier, notably in solution.
  • the outmost shell can be made from at least one polymer, and preferably can be made from at least one polymer selected from the group consisting of polysaccharides and derivatives, acrylic or methacrylic acid homopolymers or copolymers or salts and esters thereof, polystyrene-maleic anhydride copolymer, and their mixture, such as poly (meth) acrylate, cellulose ether, cellulose ester and derivatives, and their mixture.
  • the content of said outmost shell is selected, in terms of total weight of microcapsule, from 0.1 to 20.0 %by weight and preferably from 0.5 to 15%by weight.
  • the shell coating may be meaningless, and when it is more than 20.0 %by weight, a feeling of foreign substances may be caused.
  • the thickness of an outmost shell is not particularly limited and may be suitably chosen according to the finally desired color-changing microcapsule.
  • the outmost shell may have a thickness which is larger than 20 ⁇ m, particularly 30 ⁇ m, preferably 40 ⁇ m, more preferably 50 ⁇ m, and which is smaller than 200 ⁇ m, particularly 150 ⁇ m, preferably 120 ⁇ m, more preferably 90 ⁇ m.
  • microcapsules of the current invention comprise:
  • a core comprising:
  • -a coloured core which comprises at least one colorant and optionally at least one binder
  • one or more inner color layer (s) surrounding the coloured core comprising at least one colorant, and at least one binder,
  • a shell having at least one pressure-breakable wall layer, comprising at least one colorant b) a shell having at least one pressure-breakable wall layer, comprising at least one colorant.
  • colorant includes any synthetic or natural, or organic or inorganic pigments, dyes or lakes, and any colorants approved by CTFA and the FDA.
  • the colorant may be water-soluble or water-dispersible, or oil-soluble or oil-dispersible or with limited solubility in water.
  • colorant refers to organic pigments such as synthetic or natural dyes selected from any of the well-known FD&C or D&C dyes, inorganic pigments such as metal oxides, or lakes such as the ones based on cochineal carmine, barium, strontium, calcium or aluminum and any combination (blend) thereof.
  • insoluble salts of sodium, potassium, calcium, baryum, aluminum, zirconium, strontium, titanium of acid colorants such as anthraquinoniques, xantheniques, pyreniques, quinoliniques, de triphenylmethane, de fluorane colorants, these colorants may include at least one carboxylic or sulfonic acid group.
  • organic pigments those having the following trade names can be mentioned:
  • the colorants are essentially inorganic pigments, more preferably a mixture of metal oxide (s) .
  • the colorants of the multi-layer microcapsules are primary metal oxides selected from iron oxides, titanium dioxide, aluminum oxide, zirconium oxides, cobalt oxides, cerium oxides, nickel oxides, tin oxide or zinc oxide, or composite oxides, more preferably an iron oxide selected from red iron oxide, yellow iron oxide or black iron oxide, or a mixture thereof.
  • a white colorant such as titanium dioxide can be chosen as a colorant for inner color layer.
  • the inner color layer may be substantially the same or similar to the titanium dioxide particles layer, and thus, it can be understood that a titanium dioxide particle layer can simultaneously plays both roles of an inner color layer and pressure-breakable wall layer.
  • a color may be achieved from one colorant alone, but most colors can be generally achieved from mixed colorants by changing the composition of colorants. Therefore, in the context of the present invention, the term “a (the) colorant” may cover both of “one colorant” and “a mixture of colorants” , if there is no specific restriction.
  • the core and pressure-breakable wall layer are made at least in part of metallicoxides, preferably iron oxides for the core and titanium dioxide for the pressure-breakable wall.
  • a binder may be employed in order to proceed the coating process and to improve the durability of coating layer.
  • a binder is selected from adhesive polymeric materials, which can act as wall-forming materials (wall-forming polymeric material) .
  • the binder is preferably selected from at least one wall-forming material, from a lipid-base material, and their mixture.
  • the binder is preferably a mixture which comprises both of a polymer as a wall-forming material and a lipid-base material as coating base.
  • the coating base refers to a hydrophilic coating base, a hydrophobic coating base, or lipid- based coating base. Since the hydrophilic coating base may be extracted together with colorant and the hydrophobic coating base may give a feeling of foreign substances due to its tow strong film property, it is preferable to employ a lipid-base coating base.
  • such lipid based material may have amphiphilic properties, that is to say having an apolar part and a polar part.
  • Such lipid-based material can include at least one or several C 12 -C 22 fatty acids chain such as selected from stearic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, etc and mixtures thereof. Preferably these fatty acids chains are hydrogenated. Eventually, these fatty acid chains may be the apolar part of a lipid-based material.
  • Lipid–based materials are amphiphilic materials having both of a polar part and an apolar part in one molecule and includes, for example, a C 12 -C 22 fatty acid chain selected from a group consisting of stearic acid, palmitic acid, oleic acid, linoleic acid, linolenoic acid, and mixture thereof. Said fatty acid chain may be hydrogenated, and optionally forms the apolar portion of the lipid-based materials.
  • Said lipid-based materials can be selected form the group consisting of a phospolipid such as phosphatidylcholine, phosphatidylethanolamine, phosphatidic acid or phosphatidylserine, a sphingolipid such as sphingosine-1-phosphate or sphingomyelin and ceramide, preferably ceramide or lecithin which is a phospholipid mixture, particularly hydrogenated lecithin.
  • a phospolipid such as phosphatidylcholine, phosphatidylethanolamine, phosphatidic acid or phosphatidylserine
  • a sphingolipid such as sphingosine-1-phosphate or sphingomyelin and ceramide
  • lecithin which is a phospholipid mixture, particularly hydrogenated lecithin.
  • the amount of lipid-based materials can be determined by considering the type and amount of wall-forming polymers as well as other components such as colorants and/or titanium dioxide particles.
  • the content of lipid-based materials can be selected, in terms of total weight of each layer, from 0.1 to 30 %by weight, particularly from 0.2 to 25%by weight, preferably from 0.3 to 20%by weight and more preferably from 0.4 to 20%by weight.
  • the breakability or dissolution ability may be decreased, and when it is more than 25 %by weight, the durability may be decreased or the stability during processing and storage may be decreased.
  • the wall-forming polymer is selected from hydrophilic polymers.
  • hydrophilic polymers means a polymer which can form hydrogen bond with water or alcohol compounds (especially elected from lower alcohols, glycol and polyol) , particularly those having O-H, N-H and S-H bonds in the molecule.
  • Said hydrophilic polymer can be selected from the following polymers or mixture thereof:
  • -polyacrylic acid/alkyl acrylate copolymers preferably modified or unmodified carboxyvinyl polymers
  • the copolymers most particularly preferred according to the present invention are acrylate/C 10 -C 30 -alkylacrylate copolymers (INCI name: Acrylates/C 10-30 Alkylacrylate Cross polymer) such as the products sold by the company Lubrizol under the tradenames Pemulen TR1, Pemulen TR2, Carbopol 1382 and Carbopol ETD2020, and even more preferentially Pemulen TR-2;
  • -AMPS/acrylamide copolymers such as the products Sepigel or Simulgel sold by the company SEPPIC, especially a copolymer of INCI name Polyacrylamide (and) C13-14 Isoparaffin (and) Laureth-7;
  • -cellulose polymers and derivatives preferably other than alkylcellulose, chosen from hydroxyethylcellulose, hydroxypropylcellulose, hydroxymethylcellulose, ethylhydroxyethylcellulose and carboxymethylcellulose, and also quaternized cellulose derivatives; in a preferred embodiment, the cellulose polymers is a carboxymethylcellulose;
  • the starch polymer is a natural starch
  • polyvinyl polymers for instance polyvinylpyrrolidones, copolymers of methyl vinyl ether and of malic anhydride, the copolymer of vinyl acetate and of crotonic acid, copolymers of vinylpyrrolidone and of vinyl acetate; copolymers of vinylpyrrolidone and of caprolactam; polyvinyl alcohol;
  • polymers of natural origin such as galactomannans and derivatives thereof, such as konjac gum, gellan gum, locust bean gum, fenugreek gum, karaya gum, gum tragacanth, gum arabic, acacia gum, guar gum, hydroxypropyl guar, hydroxypropyl guar modified with sodium methylcarboxylate groups (Jaguar XC97-1, Rhodia) , hydroxypropyltrimethylammonium guar chloride, and xanthan derivatives;
  • galactomannans and derivatives thereof such as konjac gum, gellan gum, locust bean gum, fenugreek gum, karaya gum, gum tragacanth, gum arabic, acacia gum, guar gum, hydroxypropyl guar, hydroxypropyl guar modified with sodium methylcarboxylate groups (Jaguar XC97-1, Rhodia) , hydroxypropyltrimethylam
  • -mucopolysaccharides such as hyaluronic acid and chondroitin sulfates, and mixtures thereof.
  • the hydrophilic polymers according to the invention can be selected from the group consisting of polysaccharides and its derivatives, homopolymers or copolymers of acrylic or methacrylic acid or salts and esters thereof, and their mixture.
  • Said polysaccharides and derivatives can be selected from chitosan polymers, chitin polymers, cellulose polymers, starch polymers, galactomannans, alginates, carrageenans, mucopolysaccharides, and their derivatives, and the mixture thereof.
  • Said polysaccharides and derivatives is (are) preferably selected from the group consisting of starch polymers.
  • the hydrophilic polymers can be selected from the group consisting of corn starch, polymethyl methacrylate, cellulose or its dertivatives such as carboxymethylcellulose (CMC) , cellulose ester and ether and aminocellulose, and mixture thereof.
  • CMC carboxymethylcellulose
  • the hydrophilic polymers can be selected from the group consisting of corn starch, polymethyl methacrylate, their derivatives, and mixture thereof.
  • Preferred homo-and/or co-polymer of methacrylic acid and/or methacrylic acid ester are those wherein the copolymer of methyl methacrylate and ethyl acrylate has a molecule weight from 750 to 850 kDa.
  • hydrophilic polymer (s) used as a wall-forming material in the present invention are not cross-linked.
  • the amount of polymers or wall-forming polymers can be determined by considering the type and amount of colorants, titanium dioxide particles and/or lipid-based materials.
  • the content of polymers or wall-forming polymers in each layer can be selected, in terms of total weight of each layer, from 0.1 to 30 %by weight, particularly from 0.2 to 25%by weight, preferably from 0.3 to 20%by weight and more preferably from 0.4 to 20%by weight.
  • the breakability or dissolution ability may be decreased, and when it is more than 25 %by weight, the durability may be decreased or the stability during processing and storage may be decreased.
  • hydrophilic polymers described in this part may be implemented both as shell-forming polymer and as a binder.
  • the core of the color-change microcapsules comprises:
  • (A-1) a coloured core having a size ranging from 20 ⁇ m to 800 ⁇ m comprising:
  • At least one colorant preferably selected from at least one metallic oxide, preferably from iron oxide (s) , and
  • a binder preferably selected from at least one polymer, in particular a wall-forming polymeric material, at least one lipid-based material, and their mixture ; and (A-2) at least one inner color layer surrounding the coloured core and comprising:
  • At least one colorant preferably selected from at least one metallic oxide, preferably from iron oxide (s) , and
  • a binder preferably selected from at least one polymer, , in particular a wall-forming polymeric material, at least one lipid-based material, and their mixture.
  • the color-change microcapsules include a shell further comprising any one or both of (C-1) and (C-2) :
  • (C-1) at least one outer color layer surrounding the pressure-breakable wall layer and comprising:
  • a binder preferably selected from at least one polymer, in particular a wall-forming polymeric material, at least one lipid-based material, and their mixture;
  • (C-2) an outmost shell surrounding the pressure-breakable wall layer or the outer color layer and comprising at least one shell-forming polymer, preferably selected from the group consisting of polysaccharides and derivatives, acrylic or methacrylic acid homopolymers or copolymers or salts and esters thereof, polystyrene-maleic anhydride copolymer, and their mixture, such as poly (meth) acrylate, cellulose ether, cellulose ester and derivatives, and their mixture, more preferably selected from the group consisting of polysaccharides and derivatives, acrylic or methacrylic acid homopolymers or copolymers or salts and esters thereof, and their mixture.
  • Said color-change microcapsules do not include cellulose, cellulose ether, cellulose ester and derivatives.
  • Said core does not include cellulose, cellulose ether, cellulose ester and derivatives.
  • Said inner layer does not include cellulose, cellulose ether, cellulose ester and derivatives.
  • Said pressure-breakable wall layer does not include ether, cellulose ester and derivatives.
  • Said outmost shell does not include cellulose, cellulose ether, cellulose ester and derivatives.
  • Said shell-forming polymer (s) is (are) selected from hydrophilic polymers which can form hydrogen bonds with water or alcohol compounds.
  • Said pressure-breakable wall layer (B) comprises, compared to the total weight of the pressure-breakable layer:
  • the microcapsules include titanium dioxide particles, said titanium dioxide particles being present in the microcapsule in an amount ranging from 20%to 60 %by weight, preferably from 25%to 55%by weight, more preferably from 30%to 50%by weight, relative to the total weight of the microcapsule.
  • the microcapsules include iron oxide particles, said iron oxide particles being present in the microcapsule in an amount ranging from 20%to 60%by weight, preferably from 25%to 55%by weight, more preferably from 30%to 50%by weight, relative to the total weight of the microcapsule;
  • Said lipid-based material is selected from sphingolipids or phospholipids, preferably selected from ceramide, (hydrogenated) lecithin, and their mixture.
  • the ratio between the radius of the core and the thickness of the shell is selected from 1:0.05 to 1:0.5.
  • Said microcapsules include at least one inner color layer having a thickness of 20 to 200 ⁇ m and an outer color layer having a thickness of 20 ⁇ m to 200 ⁇ m.
  • the microcapsules implemented in the cosmetic composition according to the present invention are preferentially at least in part prepared by a fluid-bed process, especially a fluidized-bed coating process.
  • the specificity of the fluid-bed process is that it leads to real capsules compared to spray drying, which leads to granular particles by particle cohesion or to a matrix with the core material randomly dispersed in a polymer.
  • the use of fluid-bed process allows having substantially spherical microcapsules with an core substantially spherical, surrounded by at least one layer circumferentially surrounding said core and preferably at least one outer layer circumferentially surrounding said inner layer.
  • Fluid bed process is disclosed by example in‘Fluid-Bed Coating, Teunou, E.; Poncelet, 2005, D.
  • a man skilled in the art knows how to adjust air quantity, liquid quantity and temperature allowing reproducing a microcapsule according to the invention.
  • a fluid bed process implemented includes Würster process and/or tangential spray process.
  • Würster process allows, contrary to pelletization process, to conduct to spherical capsules with core surrounded by one or more circumferential layers.
  • the multi-layers coating contains at least starch as polymer with at least one lipid-based material and preferably lecithin.
  • the microcapsules additionally include lipid-based material chosen from phospholipids, advantageously selected from phosphoacylglycerol and in particular lecithins.
  • the microcapsules include at least three or more different colorants (in terms of color) .
  • said colorants are inorganic pigments, more preferably metal oxide (s) .
  • an organic solvent may be employed in the preparation of coating solution used in the fluidized bed coating process.
  • the organic solvent which can be used in the present invention is not specifically restricted but preferably includes methylene chloride, methanol, ethanol, and mixture thereof. It is possible to employ any organic solvent if it can dissolve or disperse the polymers and/or lipid-based materials, has a boiling point less than that water, and has a low residual toxicity.
  • microcapsules according to the invention are obtainable, and preferably obtained, by the following steps:
  • step (c-2) optionally coating the particles obtained in the above step (b) or (c-1) with a solution in which a shell-forming polymer is dissolved or dispersed to form an outmost shell.
  • binder (s) comprise (s) is selected from a polymer, a lipid-based material, and their mixture.
  • Said polymer and a lipid-based material may be the same or different from each other.
  • each coating in the steps (a-2) , (b) , (c-1) and (c-2) can be performed by the fluidized bed process.
  • the layer surrounding the coloured core is made by fluidized bed coating process.
  • every layers surrounding the coloured core are made by fluidized bed coating process.
  • the outmost shell surrounding the layer (s) is made by fluidized bed coating process.
  • said solution in the above steps can employs as a solvent such as water or organic solvents having a low-boiling point, for example, at least one selected from a group consisting of methylene chloride, methanol and ethanol.
  • a solvent such as water or organic solvents having a low-boiling point, for example, at least one selected from a group consisting of methylene chloride, methanol and ethanol.
  • Mixed colorant particles are introduced into a fluidized bed coating system (Glatt GPOG 1) and subjected to a coating with the inner color coating solution to obtain a coloured core particle coated with an inner color layer.
  • Gelatt GPOG 1 a fluidized bed coating system
  • a coating of the coloured core particle coated with an inner color layer with the resulting titanium dioxide particle coating solution is carried out by a fluidized bed process to obtain particles having a coloured core –an inner color layer –titanium dioxide particle layer.
  • Pigment Capsule comprises mixed Pigment 96.70%, Zea Mays (corn) Starch 2.65%, Hydrogenated Lecithin 0.65%, and the mixed Pigment comprises SunPURO TM Yellow Iron Oxide 49.2%, SunPURO TM Red Iron Oxide 39.9%and SunPURO TM Black Iron Oxide 10.9%.
  • Pigment Capsule comprises mixed Pigment 96.60%, Zea Mays (corn) Starch 2.66%, Hydrogenated Lecithin 0.74%, and the mixed Pigment comprises SunPURO TM Yellow Iron Oxide 55.18%, SunPURO TM Red Iron Oxide 34.48%and SunPURO TM Black Iron Oxide 10.34%.
  • composition of the present invention comprises a combination of UV screening agents.
  • composition of the present invention comprises at least one UV-B screening agent, and at least one combined UV-A and UV-B screening agent.
  • the UV screening agents are classified according to UV-A and UV-B radiation wavelength range.
  • composition of the present invention comprises at least one UV-B screening agent.
  • the UV-B screening agents are chosen from hydrophilic UV-B screening agents, hydrophobic UV-B screening agents, or a mixture thereof.
  • hydrophilic UV-B screening agent means any organic or mineral UV-B screening agent capable of being fully dissolved in molecular form in a liquid aqueous phase or of being dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
  • hydrophobic UV-B screening agent or “lipophilic UV-B screening agent” means any organic or mineral screening agent which can be fully dissolved in molecular state in a liquid fatty phase or which can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.
  • UV-B screening agents include those referred to hereinafter using the INCI name thereof:
  • Ethylhexyl Dimethyl PABA (ESCALOL 507 from ISP) ;
  • Ethylhexyl Salicylate particularly sold under the name "NEO HELIOPAN OS" by SYMRISE;
  • Dipropyleneglycol Salicylate particularly sold under the name "DIPSAL” by SCHER;
  • Ethylhexyl Methoxycinnamate particularly sold under the trade name "PARSOL MCX” by DSM Nutritional Products, Inc. ;
  • Etocrylene particularly sold under the trade name "UVINUL N35" by BASF;
  • Methylbenzylidene camphor sold under the name "EUSOLEX 6300" by MERCK;
  • Ethylhexyl triazone particularly sold under the trade name "UVINUL T150" by BASF;
  • UVASORB HEB Diethylhexyl Butamido Triazone particularly sold under the trade name "UVASORB HEB” by SIGMA 3V;
  • Polyorganosiloxanes with a benzalmalonate function such as Polysilicone-15 particularly sold under the trade name "PARSOL SLX” by DSM Nutritional Products, Inc. ;
  • lipophilic UV-B filters are used in the composition according to the invention:
  • PABA p-aminobenzoic acid
  • PEG-25 PABA particularly sold under the trade name "UVINUL P25" by BASF.
  • Phenylbenzimidazole Sulfonic Acid particularly sold under the trade name "EUSOLEX 232" by MERCK,
  • the UV-B screening agent of the present invention is hydrophilic UV-B screening agent.
  • the preferred hydrophilic UV-B screening agent is cinnamates, and more preferably ethylhexyl methoxycinnamate.
  • the UV-B screening agent (s) is (are) present in an amount ranging from 1%to 20%by weight, preferably from 1%to 15%by weight, and more preferably from 3%to 10%by weight relative to the total weight of the composition.
  • composition of the present invention comprises at least one combined UV-A and UV-B screening agent, said screening agent is chosen from the group consisting of:
  • Benzophenone-1 (2, 4-dihydroxybenzophenone) , marketed under the trademark “Uvinul 400” by BASF;
  • Benzophenone-2 (Tetrahydroxybenzophenone) , marketed under the trademark “Uvinul D50” by BASF;
  • Benzophenone-3 (2-hydroxy-4-methoxybenzophenone) or oxybenzone, marketed under the trademark “Uvinul M40” by BASF;
  • Benzophenone-4 (hydroxymethoxy benzophonene sulfonic acid) , marketed under the trademark “Uvinul MS40” by BASF;
  • Benzophenone-5 (Sodium hydroxymethoxy benzophenone Sulfonate) ;
  • Benzophenone-6 (dihydroxy dimethoxy benzophenone) ; marketed under the trademark “Helisorb 11” by Norquay;
  • Benzophenone-8 marketed under the trademark “Spectra-Sorb UV-24” by American Cyanamid;
  • Benzophenone-9 (Disodium dihydroxy dimethoxy benzophenonedisulfonate) , marketed under the trademark “Uvinul DS-49” by BASF;
  • Amino-substituted hydroxybenzophenone compounds such as n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate (UVINUL Aplus granular by BASF) ; 1, 1'- (1, 4-piperazinediyl) bis [1- [2- [4- (diethylamino) -2-hydroxybenzoyl] phenyl] -methanone (CAS 919803-06-8) ;
  • Methylene bis- (hydroxyphenylbenzotriazol) compounds such as 2, 2’-methylenebis [6- (2H-benzotriazol-2-yl) -4-methyl-phenol] marketed in the solid form under the trademark “Mixxim BB/200” by Fairmount Chemical, 2, 2’-methylenebis [6- (2H-benzotriazol-2-yl) -4- (1, 1, 3, 3-tetramethylbutyl) phenol] marketed in the micronized form in aqueous dispersion under the trademark “Tinosorb M” by BASF, or under the trademark “Mixxim BB/100” by Fairmount Chemical, and the derivatives as described in U.S. Pat. Nos. 5,237,071 and 5,166,355, GB-2,303,549, DE-197,26,184, and EP-893,119;
  • Drometrizole trisiloxane marketed under the trademark “Silatrizole” by Rhodia Chimie or “Mexoryl XL” by L’Oreal, as represented below.
  • the composition comprises at least one combined UV-A and UV-B screening agent selected from the group consisting of amino-substituted hydroxybenzophenone compounds, drometrizole trisiloxane, or a mixture thereof.
  • the combined UV-A and UV-B screening agent is selected from n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate, drometrizole trisiloxane, or a mixture thereof.
  • the combined UV-A and UV-B screening agent is present in an amount from 0.01%to 10%by weight, preferably from 0.1%to 5%by weight, relative to the total weight of the composition.
  • composition of the present invention further comprises additional UV screening agents, which are different from the ones disclosed above.
  • the present invention relates to a composition for treating keratin materials, comprising:
  • UV-B screening agent chosen from cinnamates; and from 0.1%to 5%by weight of at least one combined UV-A and UV-B screening agent selected from the group consisting of amino-substituted hydroxybenzophenone compounds, drometrizole trisiloxane, or a mixture thereof.
  • composition in accordance with the present invention may further comprise an oily phase.
  • the oily phase is a dispersed oily phase.
  • oil means any fatty substance that is in liquid form at room temperature (20-25°C) and at atmospheric pressure.
  • the “fatty substance” comprises at least one hydrocarbon chain "fat” that is to say a linear hydrocarbon chain of at least 4 carbon atoms, unsaturated or not unsaturated, optionally substituted, in particular a linear hydrocarbon chain C 5 -C 30 .
  • the oily phase that is suitable for preparing the cosmetic compositions according to the invention may comprise hydrocarbon-based oils, silicone oils, fluoro oils or non-fluoro oils, or mixtures thereof.
  • the oils may be volatile or non-volatile.
  • They may be of animal, plant, mineral or synthetic origin.
  • non-volatile oil means an oil of which the vapour pressure at 25°Cand atmospheric pressure is non-zero and is less than 0.02 mmHg (2.66 Pa) and better still less than 10 -3 mmHg (0.13 Pa) .
  • volatile oil means an oil of which the vapour pressure at 25°Cand atmospheric pressure is from 0.001 to 300 mmHg (0.13 Pa to 40000 Pa) , and preferably from 0.01 to 10 mmHg (1.3 Pa to 1300 Pa) .
  • silicon oil means an oil comprising at least one silicon atom, and especially at least one Si-O group.
  • fluoro oil means an oil comprising at least one fluorine atom.
  • hydrocarbon-based oil means an oil mainly containing hydrogen and carbon atoms.
  • the oils may optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl or acid radicals.
  • the oily phase is present in an amount ranging from 1%to 50%by weight, preferably from 5%to 35%by weight, relative to the total weight of thecomposition.
  • compositions of the invention may further comprise an aqueous phase.
  • the aqueous phase is a continuous aqueous phase.
  • the aqueous phase includes water, as the case may be, in a mixture with water-soluble additives and/or solvents.
  • the aqueous phase may also comprise organic solvents miscible with water (at room temperature-25°C) such as for example monoalcohols having from 2 to 6 carbon atoms such as ethanol, isopropanol; polyols notably having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having from 2 to 6 carbon atoms, such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylylglycol, dipropylene glycol, diethylene glycol; glycol ethers (notably having from 3 to 16 carbon atoms) such as mono-, di-or tri-propylene glycol (C 1 -C 4 ) alkyl ethers, mono-, di-or tri-ethylene glycol (C 1 -C 4 ) alkyl ethers and mixtures thereof.
  • organic solvents miscible with water such as for example monoalcohols having from 2 to 6
  • the aqueous phase may further comprise at least one hydrophilic thickening agent.
  • suitable thickening agents include the carboxyvinyl polymers such as the products (Carbomers) and the Pemulen products, for instance Pemulen and Pemulen (acrylate/C 10 -C 30 alkyl acrylate copolymer) ; polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel (CTFA name: polyacrylamide/C 13-14 isoparaffin/laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyltaurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, for instance poly (2-acrylamido-2-methylpropanesulfonic acid) sold by the company Hoechst under the trade name “Hostacer
  • the aqueous phase is present in an amount ranging from 50%to 99%by weight, preferably from 55%to 90%by weight, relative to the total weight of the composition.
  • compositions in accordance with the present invention may also comprise conventional cosmetic additives chosen in particular from softeners, humectants, additional opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, additional active agents, fillers, polymers, propellants, acidifying or basifying agents or any other ingredient commonly used in the cosmetic and/or dermatological field.
  • conventional cosmetic additives chosen in particular from softeners, humectants, additional opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, additional active agents, fillers, polymers, propellants, acidifying or basifying agents or any other ingredient commonly used in the cosmetic and/or dermatological field.
  • composition of the present invention can be used for a non-therapeutic process, such as a cosmetic process or method, for treating keratin materials, such as the skin, in particular the face and the lips, by being applied to the skin, especially the face and the lips.
  • a non-therapeutic process such as a cosmetic process or method
  • keratin materials such as the skin, in particular the face and the lips
  • the present invention also relates to a use of the composition according to the present invention, as it is or in cosmetic product for making up/caring for keratin materials, in particular the skin, especially for the face and the lips.
  • the present invention relates to a non-therapeutic process for caring for and/or making up keratin materials, comprising the application, to the surface of the said keratin material, of at least one composition of the invention.
  • the present invention relates to a cosmetic method for caring for and/or making up the skin, comprising the application to the skin of an anhydrous composition as defined above.
  • the present invention also relates to use of the composition as defined above, for the preparation of composition intended to whitening or brightening the skin.
  • Comparative formulas 1’and 2’ comprise UV-A screening agents which are outside of the invention, among which:
  • Comparative formula 1 contains, as a combined UV-A and UV-B screening agent, BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE, which is outside the scope of the present invention, and
  • Comparative formula 2 contains a UV-A screening agent BUTYL
  • phase B2 mixing phase B2 into B1 to make phase B at 65-75°Cuntil homogeneous;
  • phase B mixing phase B into phase A with high agitation efficiency until homogeneous
  • phase F added to the mixture obtained above under 20-30°Cusing low Rayneri agitation until homogenization.
  • the evaluation of the sensory of the invention and comparative formulas was conducted by applying on skin the invention and comparative formulas, respectively, and then evaluating the oily residue on skin by 5 experts.
  • the score ranging from 1 to 5 represents the level of oily residue on the skin, the higher the number is, the more the oil left on the skin.
  • a score between 2.5 and 4.5 represents a “just-right” sensory, which means that the skin is not too dry or too oily; the oil residue on the skin is at a proper level to moisturize the skin without a feeling of being oily.
  • SPF sun protection factor
  • PPD skin darkening that persists more than 2 h after the end of UVA exposure. It is determined according to ISO 24442: 2011 (en) Cosmetics-Sun protection test methods-In vivo determination of sunscreen UVA protection.
  • invention formulas 1, 2, and comparative formula 2’ have good anti-UV effect, with SPF value greater than 15, and PPD value greater than 2, which are considered as good anti-UV protection.
  • Comparative formula 1 is not subjected to the test as it is not stable.

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Abstract

L'invention concerne une composition de traitement de matières kératiniques comprenant a) au moins un dérivé de diphénylméthane hydroxylé de formule (I) <img file="885021dest_path_image001.jpg" he="51,59" img-content="drawing" img-format="jpg" inline="yes" orientation="portrait" wi="113,24"/> dans laquelle R1 est choisi parmi un atome d'hydrogène, un groupe méthyle, une chaîne alkyle linéaire ou ramifiée saturée ou insaturée contenant 2 à 4 atomes de carbone, un groupe -OH et un atome d'halogène, R2 est choisi parmi un atome d'hydrogène, un groupe méthyle, une chaîne alkyle linéaire ou ramifiée saturée ou insaturée contenant 2 à 5 atomes de carbone, R3 est choisi parmi un groupe méthyle ou une chaîne alkyle linéaire ou ramifiée saturée ou insaturée contenant 2 à 5 atomes de carbone, R4 et R5 sont, indépendamment l'un de l'autre, choisis parmi un atome d'hydrogène, un groupe méthyle, une chaîne alkyle linéaire ou ramifiée saturée ou insaturée contenant 2 à 5 atomes de carbone, un groupe -OH ou un atome d'halogène ; b) des microcapsules changeant de couleur ; c) au moins un agent écran contre les UV-B ; et au moins un agent écran contre les UV-A et les UV-B combinés choisi dans le groupe constitué de composés de benzophénone, de composés phénylbenzotriazoles éventuellement substitués par un groupe amino ou d'un mélange de ceux-ci.
PCT/CN2015/095675 2015-11-26 2015-11-26 Composition comprenant des microcapsules WO2017088146A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021114024A1 (fr) * 2019-12-09 2021-06-17 L'oreal Composition pour éclaircir et/ou blanchir des matières kératiniques

Citations (4)

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Publication number Priority date Publication date Assignee Title
WO2009138978A2 (fr) * 2008-05-12 2009-11-19 Tagra Biotechnologies Ltd Compositions pour application topique comprenant des colorants microencapsulés
US20120027700A1 (en) * 2010-07-29 2012-02-02 Conopco, Inc., D/B/A Unilever Skin care compositions comprising substituted diamines
WO2013107001A1 (fr) * 2012-01-17 2013-07-25 L'oreal Composition à changement de couleur contenant un ou plusieurs filtres uv
WO2014170239A1 (fr) * 2013-04-14 2014-10-23 Symrise Ag Composition pour éclaircir la peau et les cheveux

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009138978A2 (fr) * 2008-05-12 2009-11-19 Tagra Biotechnologies Ltd Compositions pour application topique comprenant des colorants microencapsulés
US20120027700A1 (en) * 2010-07-29 2012-02-02 Conopco, Inc., D/B/A Unilever Skin care compositions comprising substituted diamines
WO2013107001A1 (fr) * 2012-01-17 2013-07-25 L'oreal Composition à changement de couleur contenant un ou plusieurs filtres uv
WO2014170239A1 (fr) * 2013-04-14 2014-10-23 Symrise Ag Composition pour éclaircir la peau et les cheveux

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Title
SHU PENG ET AL.: "Preparaton and stability study of a lightenting emulsion", CHINA SURFACTANT DETERGENT & COSMETICS, vol. 44, no. 11, 30 November 2014 (2014-11-30), ISSN: 1001-1803 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021114024A1 (fr) * 2019-12-09 2021-06-17 L'oreal Composition pour éclaircir et/ou blanchir des matières kératiniques
CN115209862A (zh) * 2019-12-09 2022-10-18 莱雅公司 用于增亮和/或增白角蛋白材料的组合物

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