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WO2000047167A1 - Compositions cosmetiques et pharmaceutiques contenant un systeme de coloration cristalline et procede de preparation associe - Google Patents

Compositions cosmetiques et pharmaceutiques contenant un systeme de coloration cristalline et procede de preparation associe Download PDF

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Publication number
WO2000047167A1
WO2000047167A1 PCT/US2000/001354 US0001354W WO0047167A1 WO 2000047167 A1 WO2000047167 A1 WO 2000047167A1 US 0001354 W US0001354 W US 0001354W WO 0047167 A1 WO0047167 A1 WO 0047167A1
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Prior art keywords
composition
spheres
cosmetic
arrays
surfactant
Prior art date
Application number
PCT/US2000/001354
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English (en)
Inventor
Konstantinos M. Lahanas
Gheorghe Cioca
Original Assignee
Color Access, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Color Access, Inc. filed Critical Color Access, Inc.
Priority to AU24164/00A priority Critical patent/AU2416400A/en
Publication of WO2000047167A1 publication Critical patent/WO2000047167A1/fr

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Classifications

    • 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
    • A61K8/025—Explicitly spheroidal or spherical shape
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; 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
    • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • A61K8/70—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes

Definitions

  • the present invention relates to useful cosmetic or pharmaceutical compositions having color without the use of traditional pigments or dyes.
  • the invention relates to a composition containing crystalline colloidal arrays suspended m an aqueous medium which are capable of producing iridescent colors.
  • liquid crystals are a well known phenomenon. They exist as an intermediate phase between the liquid phase and the solid phase. Certain organic compounds are capable of existing as liquid crystals because of their rod-like crystalline shape and the attractive forces of the molecules There are two types of liquid crystal mesophases.
  • the smectic mesophase is one which constitutes a long range ordering that is of a substantially lamellar type (i.e., they are arranged in raft like layers).
  • the nematic mesophase is ordered substantially linearly (i.e., the molecules are lined up whereby the long axes of the molecules are parallel) Molecules of liquid crystals are arranged in a periodic fashion in at least one direction.
  • this type of liquid crystals depending on the structure of the liquid crystal, in that their chemical stability, temperature and light stability, especially UV light stability, is relatively low.
  • liquid crystals are limited to use m hydrophilic systems because they suspend better in these systems. In hydrophobic systems, the crystals dissolve and their structure breaks down
  • the present invention provides cosmetic or pharmaceutical compositions for topical application to the skin comp ⁇ smg a colo ⁇ ng system which comp ⁇ ses a colloidal crystalline array (hereinafter referred to as "CCAs") m an aqueous medium
  • CCAs colloidal crystalline array
  • the color of the composition is produced by light directed at and diffracted by the arrays of the colo ⁇ ng system.
  • the invention also provides for a method for preparing a cosmetic or pharmaceutical composition having a coloring system compnsmg adding CCAs to a cosmetically or pharmaceutically acceptable aqueous medium
  • the present invention comprises a coloring system for cosmetic or pharmaceutical compositions using a system of colloidal crystalline arrays to advantageously provide rainbow-like appealing colors.
  • the synthesis of monodisperse spherical particles and CCAs composed thereof which produce an mdescent color is known and described in, for example, U.S. Patent Nos.4,627,689, 4,632,517, and 5,452,123, the contents of which are incorporated herein by reference. In these patents, a crystalline colloidal narrow band radiation filter and methods for making switching devices and related devices using CCAs are disclosed.
  • CCAs Although, the ability of CCAs to produce an iridescent color is known, a water based cosmetic or pharmaceutical composition colored by a colo ⁇ ng system of CCAs has not previously been suggested in the prior art. In addition, particular cosmetic materials have been found that do not interfere with the structure of the CCA.
  • the color of the CCA coloring system is produced as light travels through and is diffracted by the crystalline structure of the CCA.
  • the CCAs are composed of spherical particles that are capable of self-assembly. The uniform particle size and surface charge density of the spheres cause coulombic electrostatic repulsive forces between them and allow the spheres to "self-assemble" into crystalline lattice structures which efficiently diffract light meeting the Bragg condition. See Asher, S.A., et al, "Novel Optically Responsive and
  • the spheres arrange themselves in an order such that there are at least two planes running through the array. Each of the planes is parallel to one another and has an angle incident thereto. The distance between the planes is determined by the number density of the particles, the particle size and the surface charge. Because the spacing of CCAs is similar to the wavelength of visible and near-LR light, strong Bragg diffraction of light occurs as it travels through the CCAs. The creation of color, by the self-assembly of the spheres into CCAs, is partially dependent on the concentration density of the spheres.
  • compositions of the present invention can produce any color.
  • color herein is not only understood to mean the color impression of the wavelength region of visible light perceivable by the human eye, but also the color impression of the adjacent UV and LR wavelength regions not perceivable by the human eye but measurable by known instruments, such as UV and LR spectrometers or goniometers.
  • the color is iridescent like a precious opal and the color is clear, sharp and shiny
  • the production of color based on the number density ranges from the red region through to the blue region of the spectrum.
  • a lower number density for a particular particle size and composition may produce color in the red region, while at the other end of the spectrum, a higher number density may produce color m the blue region.
  • the colors of mdigo and violet may also be achieved with a higher number density.
  • the number density of the spheres is about 1 to about 95 percent of the composition, preferably from about 5 to about 50 percent, more preferably it is from about 10 to about 25 percent.
  • An advantage of the present invention is the ability to produce a dilute concentration of spheres capable of giving off a clear and stable rainbow type of color in a water based cosmetic or pharmaceutical composition.
  • the spheres can be natural or treated cross linked materials or other mate ⁇ als having a refractive index value of greater than about 1.0, preferably between 1.5 and 3.0.
  • the spheres of the CCAs are formed by treating at least one precursor and a surfactant.
  • the general process involves emulsion polymerization or condensation of the precursor and the surfactant to form spherical particles of monodisperse uniform particle size and uniform surface charge density.
  • Known polyme ⁇ zation techniques such as, for example, dispersion or emulsion polyme ⁇ zation or condensation processes are described m Bhattacharyya, Bhupati and Halpern, B. David, "Application of Monodisperse Functional and Fluorescent Latex Particles", Polymer News 4, pps. 107-114 (1977); incorporated herein by reference. Preparation of CCAs is also described, in U.S. Patent No. 4,632,517.
  • the spherical particles of CCAs can be formed by combining the precursor and the surfactant with deiomzed, doubly distilled water and allowing it to polyme ⁇ ze in a water bath until crystal formation is complete, usually about 4 to 8 hours. Crystal formation is verified by the appearance of an iridescent color.
  • the amount and type of precursor, and the amount of surfactant are factors which determine the concentration density of the spheres and consequently, the self-assembly of the spheres into CCAs.
  • any one or more organic or inorganic precursors which are capable of combining to form spherical colloidal particles that have a monodisperse uniform particle size and uniform surface charge density can be used in the present invention.
  • the term "monodisperse” as used herein desc ⁇ bes a particle size distribution of the spheres which is gaussian and has a low standard deviation (i.e., standard deviation of less than 5 percent of the mean).
  • the precursor can be any material capable of assembling into an ordered array dispersed throughout a solvent.
  • the precursors are selected from the group consisting of methacryhc acid and derivatives thereof such as, for example, polymethylmethacrylate (hereinafter referred to as "PMMA"), silicon alkoxides and hydroxides such as, for example, silica (e.g. silicon dioxide), aluminum alkoxides such as, for example, aluminum dioxide, polytetrafluoroethylene, styrene and polymers thereof such as for example, polystyrene, titanium alkoxides such as for example, titania, and divmylbenzene.
  • PMMA polymethylmethacrylate
  • silicon alkoxides and hydroxides such as, for example, silica (e.g. silicon dioxide)
  • aluminum alkoxides such as, for example, aluminum dioxide, polytetrafluoroethylene
  • styrene and polymers thereof such as for example, polystyrene
  • titanium alkoxides such as for example, titania, and divmyl
  • the precursor is PMMA, polystyrene, or silica. See Tse et al., supra. Most preferably, the precursor is polystyrene.
  • the precursor is combined with the surfactant, the amount of which can vary depending on the desired particle size of the spheres. In general, there is an inverse relationship between the amount of surfactant and the size of the spheres (i.e., lower amounts of surfactant produce larger sized spherical particles.)
  • the amount of surfactant is about 0.01 to about 10 percent of the weight of the composition.
  • the surfactant has an HLB of greater than about 12. Examples of suitable surfactants include but are not limited to M A-
  • the spheres have an average particle size of about 100 to about 1500 nm in diameter. More preferably, the spheres have an average particle size of about 1000 to about 1300 nm
  • the variation in particle size should preferably be less than about 5 percent of the mean.
  • the uniform particle size promotes the equalization of the repulsive forces between the spheres and therefore, assists the spheres in the process of self-assembly.
  • the order in which the spheres of a CCA arrange themselves is based on the repulsive forces between them.
  • the spheres have a highly uniform surface charge density.
  • the spheres have a surface charge density of about 0.5 to about 30 ⁇ C/cm 2 , preferably about 1 to about 5 ⁇ C/cm 2 .
  • the H " or OH ions are predominantly found on the surface of the sphere on what is commonly referred to as the electrical double layer.
  • Each of the spheres can have either a smooth or a hairy charged surface. See Ottewill, Ronald H., “Colloidal Properties of Latex Particles ", Scientific Methods for the Study of Polymer Colloids and Their Applications. 129, 130 (1990); incorporated herein by reference.
  • the electrical double layer affects the repulsive forces between the spheres and thus, affects their process of self-assembly.
  • the counter-ion cloud of each sphere surrounds the electrical double layer at the surface of the sphere.
  • the counter-ion clouds associated with each of the spheres there is a slight overlap of the counter-ion clouds associated with each of the spheres.
  • the spheres repel each other due to the repulsive forces caused by the counter-ions.
  • the CCA formed by the self-assembly of the spheres is a result of the repulsive forces between them.
  • the energy is greater than about kT, where k is the Boltzmann constant and T is the absolute temperature, the spheres are able to self-assemble.
  • a highly pure medium is necessary to prevent mterfenng with the surface charge density of the spheres and thus, disrupting the process of self-assembly into CCAs.
  • the term "pure” refers to a substantial lack of impurities m the medium in the form of ions and can be expressed in terms of conductivity of the medium.
  • a highly pure medium has a low ionic strength due to a low level of ionic impu ⁇ ties. If the ionic strength is too high, flocculation may occur and the color dissipates. This phenomenon can occur locally within the medium or throughout the medium.
  • the medium has a relatively low ionic strength.
  • the medium has a conductomet ⁇ c reading of less than about 2.5 ⁇ "1 indicating that the ionic purity of the medium is sufficient for CCAs to form. More preferably, the medium is non-ionic.
  • the spheres are dispersed m an aqueous medium which can include any low ionic or non-ionic solvent that is miscible in water and is stable so that it does not produce degradant ions at a later time.
  • the medium is predominantly aqueous and can also include solvents such as, for example, hydroalcohol, glyce ⁇ n, and combinations thereof.
  • solvents such as, for example, hydroalcohol, glyce ⁇ n, and combinations thereof.
  • acceptable hydroalcohols include, but are not limited to ethanol, propanol, or glycols such as polyethylene glycol.
  • the medium is aqueous, however, if the medium is partially nonaqueous, preferably the nonaqueous portion is present in an amount no greater than about 50 percent, more preferably it is no greater than about 30 percent.
  • Co-polyme ⁇ zation treatment of the spherical particles can improve the self-assembly of the spheres. Further treatment of the spheres after initial polymerization can render the surface charge density more uniform. Even though the polymerized spherical particles may have a natural surface charge density, co-polyme ⁇ zation of the spheres enhances the uniformity of the surface charge density
  • Types of co-polyme ⁇ zation treatment can involve, for example, adding an anionic comonomer The aniomc property of the comonomer causes the surface charge density of the particles to increase. In turn, the increased surface charge density causes an intensification of the electric forces which form and maintain the self- assembly of the spheres into the CCA, thereby strengthening the CCA.
  • Comonomers with anionic groups for copolyme ⁇ zation include for example, but are not limited to, the 1- sodium, 1 -allyloxy-2-hydroxypropane sulfonate (COPS- 1 ), sodium salt of styrene sulfonate, 2-acrylam ⁇ do-2 -methyl-propane sulfonate, 3-sulfopropyl methacrylate potassium salt, and vinyl sulfonate.
  • COPS- 1 1- sodium, 1 -allyloxy-2-hydroxypropane sulfonate
  • sodium salt of styrene sulfonate 2-acrylam ⁇ do-2 -methyl-propane sulfonate
  • 3-sulfopropyl methacrylate potassium salt 2-vinyl methacrylate
  • Post-polyme ⁇ zation treatment such as for example, deiomzation techniques, can reduce the ionic strength of the medium
  • this treatment include but are not limited to dialysis, cent ⁇ fugation, pu ⁇ fication using an ion exchange column, or any other similar apparatus or method appropriate for removing ions or surfactant from the system. Any ions remaining, after purification, are most likely part of the electrical double layer (i.e., ions distributed close to the surface of the sphere and part of the counter ionic cloud which surrounds the sphere.) More than one post-polymerization technique can be applied.
  • the post-polyme ⁇ zation treatment can also include a combination of the techniques mentioned above (i.e., addition of the anionic comonomer and purification) to improve the surface charge density of the particles and to reduce the ionic strength of the medium.
  • the spheres it is withm the scope of the present invention for the spheres to arrange themselves into any crystal structure that may be formed depending on the specific properties of the precursor and the surfactant, such as for example, the 14 Bravais lattices.
  • the spheres arrange themselves into either a face centered cubic arrangement or a body centered cubic arrangement.
  • the CCA has a face centered cubic arrangement. This arrangement represents the lowest energy state of the coloring system.
  • the CCA has a body centered cubic arrangement.
  • one of the benefits of the present invention is the ability to achieve long lasting and observable color of enhanced clarity at all angles of view of the composition, it may be desirable to add other organic and inorganic pigments and dyes to the composition. The addition of such pigments and dyes is limited, however, to those that have a low ionic strength and that will not interfere with the formation of CCAs or their continued stability once formed.
  • compositions of the present invention can be m the form of a solution, colloidal dispersion, emulsion, suspension, cream, lotion, gel, foam, or mousse which is sufficiently clear to permit the appearance of color in the product.
  • the CCA can be m the water phase of the emulsion as long as the volume of the water phase is sufficiently large to encompass the area of the CCA.
  • the compositions of the present invention can be formulated with a variety of cosmetically and/or pharmaceutically acceptable earners.
  • pharmaceutically and/or cosmetically acceptable carrier refers to a vehicle, for either pharmaceutical or cosmetic use, which vehicle holds the compositions of the present invention and which will not cause harm to humans or other recipient organisms.
  • pharmaceutical or “cosmetic” will be understood to encompass both human and animal pharmaceuticals or cosmetics.
  • the earner may be in any form appropriate to the function of the mode of delivery and that does not interfere with the stability of the CCAs.
  • compositions of the present invention can also be used pharmaceutically, and therefore may also comprise useful active ingredients, for the purposes of therapeutic treatment.
  • useful active ingredients include, but are not limited to antioxidants, antimicrobials, sunscreens, analgesics, anesthetics, anti-acne agents, antidandruff agents, antidermatitis agents, antipruntic agents, anti-inflammatory agents, antihyperkeratolytic agents, anti-dry skin agents, antiperspirants, antipso ⁇ atic agents, antiseborrheic agents, hair conditioners and hair treatment agents, antiaging agents, antiwnnkle agents, antihistamine agents, skin lightening agents, depigmenting agents, wound- healing agents, vitamins, corticosteroids, tanning agents, or hormones.
  • the inclusion of the active m the formulation is limited only by its solubility and/or stability m the aqueous medium (i.e., requiring low ionic strength) and its compatibility with the CCAs.
  • compositions may also comp ⁇ se additional preservatives, fragrances, emollients, antiseptics, stabilizers, pigments, dyes, humectants, and propellants, as well as other classes of mate ⁇ als the presence of which m the compositions may be cosmetically, pharmaceutically, or otherwise desired.
  • additional preservatives fragrances, emollients, antiseptics, stabilizers, pigments, dyes, humectants, and propellants, as well as other classes of mate ⁇ als the presence of which m the compositions may be cosmetically, pharmaceutically, or otherwise desired.
  • Preservatives employed may be m an amount of from about 0.01 to about 2 percent, preferably from about 0.01 to about 1 percent, of the formula weight.
  • suitable preservatives are BHA, BHT, propyl paraben, butyl paraben or methyl paraben or an isomer, homolog, analog or derivative thereof.
  • the present invention is further illustrated by the following non-limiting examples. EXAMPLE I COLLOIDAL CRYSTALLINE ARRAY (“CCA”)
  • Methylmethacrylic acid (MMA) and divinylbenzene (DVB) are mixed at room temperature.
  • a main vessel holding 230 g of water is heated to 80° C. While maintaining the temperature of 80° C, add sodium dodecylsulfate to the vessel. Predissolve the sodium persulfate in the remaining water and add it to the main vessel.
  • Add mixture of MMA and DVB to the vessel add COPS-1 to the vessel. Reflux the mixture for about 4 hours at 80° C. Sample is then dialyzed and treated with a mixed bed ion exchange resin to remove any remaining ions as part of the post-polymerization dialysis treatment. Dialysis is continued for 2 to 3 weeks during which time, water is changed 2 times a day.
  • Silica CCAs are commercially available from Ikeda Corporation of America, Island Park, NY, as Opalesque 1015 and 1030.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions cosmétiques ou pharmaceutiques qui comprennent un système de coloration contenant des réseaux colloïdaux cristallins dans un milieu. L'invention concerne également un procédé de préparation d'une composition cosmétique ou pharmaceutique, qui consiste à ajouter à un milieu des réseaux colloïdaux cristallins. Les systèmes de coloration produisent une couleur limpide, notamment une couleur iridescente, sans adjonction de pigments ou de colorants. La couleur est durable et peut être observée de n'importe quel angle de vue de la composition.
PCT/US2000/001354 1999-02-09 2000-01-19 Compositions cosmetiques et pharmaceutiques contenant un systeme de coloration cristalline et procede de preparation associe WO2000047167A1 (fr)

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AU24164/00A AU2416400A (en) 1999-02-09 2000-01-19 Cosmetic and pharmaceutical compositions containing crystalline color system andmethod of preparing same

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US24645099A 1999-02-09 1999-02-09
US09/246,450 1999-02-09

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EP1210946A1 (fr) * 2000-12-01 2002-06-05 Neutrogena Corporation Composition astringente et méthode d'utilisation
FR2819410A1 (fr) * 2001-01-18 2002-07-19 Oreal Composition cosmetique irisee et ses utilisations
FR2819412A1 (fr) * 2001-01-18 2002-07-19 Oreal Composition cosmetique irisee et ses utilisations
FR2819411A1 (fr) * 2001-01-18 2002-07-19 Oreal Composition cosmetique irisee et ses utilisations
US6589452B2 (en) * 2000-02-23 2003-07-08 University Of Pittsburgh Photochemically controlled photonic crystal diffraction
EP1281389A3 (fr) * 2001-08-04 2004-02-04 Beiersdorf AG Preparations cosmetiques et dermatologiques de protection solaire comprenant des particules de latex et des derives de triazine a substitution asymetrique
WO2004054525A1 (fr) * 2002-12-13 2004-07-01 Unilever Plc Compositions capillaires traitantes
WO2006097332A3 (fr) * 2005-03-16 2006-12-07 Unilever Plc Compositions colorantes et utilisation
WO2006136721A1 (fr) * 2005-06-22 2006-12-28 L'oreal Compositions de maquillage des matieres keratiniques
KR100792048B1 (ko) * 2003-08-22 2008-01-04 이-엘 매니지먼트 코포레이션 콜로이드성 결정성 어레이를 포함하는 국소 전달 조성물
FR2950249A1 (fr) * 2009-09-24 2011-03-25 Oreal Utilisation de dispersion de particules polymeriques rigides pour generer un effet coloriel
CN107082837A (zh) * 2017-05-12 2017-08-22 山东大学 一种粒径和表面电荷可控的单分散聚苯乙烯微球的制备方法
FR3104988A1 (fr) * 2019-12-20 2021-06-25 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre une composition comprenant des particules monodisperses à base d’au moins un polymère cationique et une étape de séchage à l’aide d’un dispositif de séchage à air pulsé
FR3104950A1 (fr) * 2019-12-20 2021-06-25 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre une composition comprenant des particules monodisperses à base d’au moins un polymère non-ionique et une étape de séchage à l’aide d’un dispositif de séchage à air pulsé

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FR3104950A1 (fr) * 2019-12-20 2021-06-25 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre une composition comprenant des particules monodisperses à base d’au moins un polymère non-ionique et une étape de séchage à l’aide d’un dispositif de séchage à air pulsé

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