WO2016001168A1 - Utilisation cosmétique, en tant qu'agent actif matifiant, d'un matériau siliceux cationique ou amphiphile - Google Patents

Utilisation cosmétique, en tant qu'agent actif matifiant, d'un matériau siliceux cationique ou amphiphile Download PDF

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Publication number
WO2016001168A1
WO2016001168A1 PCT/EP2015/064738 EP2015064738W WO2016001168A1 WO 2016001168 A1 WO2016001168 A1 WO 2016001168A1 EP 2015064738 W EP2015064738 W EP 2015064738W WO 2016001168 A1 WO2016001168 A1 WO 2016001168A1
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compound
use according
siliceous material
ranging
group
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PCT/EP2015/064738
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English (en)
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Andrew Greaves
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L'oreal
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/0279—Porous; Hollow
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61Q19/008—Preparations for oily skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/008—Preparations for oily hair

Definitions

  • the present invention relates to the field of mattifying materials.
  • the invention relates to the cosmetic use, as a mattifying active agent, of a siliceous material comprising at least one amine function and in particular to the cosmetic use, as a mattifying active agent, of at least one siliceous material comprising at least one amine function, which may be obtained from at least one aminoalkyltrialkoxysilane either by hydrolysis and condensation with at least one tetraalkoxysilane, or by reaction of at least one porous precipitated amorphous silica with said aminoalkyltrialkoxysilane, these reactions also possibly being performed with at least one alkyltrialkoxysilane.
  • fillers are especially hydrophobic silica particles (hydrophobic silica aerogels) as described in WO 2013/190 112, WO 2013/160 362, WO 13/190 104 or in WO 13/194 100, or silicas functionalized with anionic groups, as described in US 2005/0 192 366.
  • Silicone elastomers are also widely used as mattifying agents, as in
  • WO 13/190 138 since they afford a soft feel on the skin. However, they must be used at a relatively high content to impart the mattifying effect, which constitutes a curb on the choice of texture and on the cost of the formulation.
  • WO 2009/120 602 describes silica silylates as sebum absorbers.
  • these fillers do not have good staying power, and their effect attenuates rapidly after a few hours.
  • Amphiphilic silica particles are also known to those skilled in the art as emulsifiers. Their amphiphilic nature is imparted by the presence both of alkyl chains (hydrophobic) and of amine chains (hydrophilic) grafted onto the particle.
  • these mattifying active agents prefferably have good cosmetic properties, in particular for them to be soft on application, to have good staying power over time and for them not to give any sensation of discomfort, dryness or coarseness either on application or after application.
  • a siliceous material comprising at least one amine function and in particular using an amino siliceous material that may be obtained from at least one aminoalkyltrialkoxysilane either by hydrolysis and condensation with at least one tetraalkoxysilane, or by reaction of at least one porous precipitated amorphous silica with said aminoalkyltrialkoxysilane, these reactions also possibly being performed with at least one alkyltrialkoxysilane.
  • a subject of the present invention is the cosmetic use, as mattifying active agent, of a siliceous material comprising at least one amine.
  • amine means a group chosen from a primary amine, and/or a secondary amine, and/or a tertiary amine and/or a quaternary amine, for example a trialkylammonium radical.
  • the electrical neutrality of the compounds is ensured by one or more identical or different cosmetically acceptable anions.
  • this anion is derived from a mineral or organic acid, such as a methosulfate anion or a halide such as chloride or bromide.
  • a subject of the present invention is the cosmetic use, as mattifying active agent, of an amino siliceous material that may be obtained from at least one aminoalkyltrialkoxysilane of formula (I) below:
  • Ri denotes a linear or branched, saturated or unsaturated Ci to Ce alkyl group, optionally interrupted with one or more groups NR, aryl and/or with one or more -O- atoms; a cyclic C3-C5 hydrocarbon-based group, or denotes a C6-C 9 aryl or C6-C 9 aryloxy group, said radicals being substituted with an amino group NRR' or N + RR'R" with R, R', R" , which may be identical or different, denoting a hydrogen atom or a C 1-C4 alkyl group, optionally substituted with one or more OH groups,
  • the groups R 2 which may be identical or different, preferably identical, denote linear or branched C 1-C4 alkyl groups, said siliceous material possibly being obtained:
  • the groups R 3 which may be identical or different, preferably identical, denote linear or branched C 1-C4 alkyl groups,
  • R5 denotes a linear or branched Ci to C 2 o, preferably C6-C 2 o, alkyl group, optionally interrupted in its chain with an O or S atom or with an amido group or a carbonyl (CO) group
  • the groups R 4 which may be identical or different, preferably identical, denote linear or branched Ci-C 4 alkyl groups.
  • the amino siliceous material used according to the invention is cationic amphiphilic, and is preferably amphiphilic.
  • amino siliceous material means a siliceous material comprising one or more identical or different radicals Ri as defined previously.
  • Said amino siliceous material may optionally comprise one or more identical or different radicals R 5 as defined previously; in this case, the amino siliceous material is amphiphilic.
  • the amino siliceous material used according to the invention is present in a composition comprising a cosmetically acceptable medium.
  • the invention relates to a cosmetic process for caring for and/or making up keratin materials, comprising a step of applying said amino siliceous material to said keratin materials, in particular to the skin, the scalp or the hair.
  • the invention relates to a cosmetic process for mattifying and/or reducing the sheen of shiny keratin materials, in particular greasy skin, greasy scalps and/or greasy hair, comprising a step of applying said amino siliceous material to said shiny keratin materials.
  • a subject of the invention is a composition comprising at least said amino siliceous material and at least one additional mattifying filler other than the amino siliceous materials of the invention.
  • the amino siliceous material used according to the invention as mattifying active agent makes it possible to obtain compositions that are comfortable and soft on application, which spread easily and uniformly, and which have mattifying and soft-focus properties.
  • the amino siliceous material used according to the invention does not give any sensation of discomfort during application and after application of the composition.
  • it has good staying power over time and, over time, it gives the skin a silky feel without any sensation of dryness or discomfort, or any coarse sensation either on application or after application.
  • compositions do not show any pilling effect on application.
  • the amino siliceous material used according to the invention makes it possible to obtain a composition that has good staying power, i.e. the mattifying effect on the keratin materials lasts for several hours.
  • the composition is used in the cosmetic field, and in particular for caring for, protecting and/or making up bodily or facial skin, the scalp and/or the hair.
  • physiologically acceptable medium is intended to mean a medium that is suitable for the topical administration of a composition.
  • a physiologically acceptable medium is preferentially a cosmetically acceptable medium, i.e. a medium that has no unpleasant odour or appearance, and that is entirely compatible with the topical administration route.
  • composition is intended for topical administration, i.e. by application at the surface of the keratin material under consideration
  • a medium is considered in particular to be physiologically acceptable when it does not cause stinging, tautness or redness that is unacceptable to the user.
  • keratin materials generally denotes the skin, especially of the face, the scalp, the nails, mucous membranes such as the lips, and also keratin fibres such as the hair or the eyelashes.
  • facial skin, the scalp and the hair are more particularly concerned by the present invention, and even more particularly facial skin.
  • said siliceous material comprises at least one Ci-6 alkyl group comprising at least one primary amine, and/or at least one secondary amine, and/or at least one tertiary amine and/or at least one quaternary amine, in particular a trialkylammonium radical, preferably tri(Ci -C6)alkylammonium.
  • the amino siliceous material contains at least one trialkylammonium radical
  • the electrical neutrality of said material is ensured by one or more cosmetically acceptable anions.
  • the amine group may be chosen more particularly from an amino radical (NH 2 ), a (di)alkylamino radical in which the alkyl chain(s) may be optionally substituted with an OH radical, a tri(Cl-C6)alkylammonium radical.
  • the amino siliceous material used according to the invention as mattifying active agent may be obtained by hydrolysis and condensation, in the presence of water, of at least one aminoalkyltrialkoxysilane of formula (I) below:
  • Ri denotes a linear or branched, saturated or unsaturated Ci to Ce alkyl group, optionally interrupted with one or more groups NR, aryl and/or with one or more -O- atoms; a cyclic C 3 -C 5 hydrocarbon-based group, or denotes a C6-C 9 aryl or C6-C 9 aryloxy group, said radicals being substituted with an amino group NRR' or N + RR'R" with R, R', R" , which may be identical or different, denoting a hydrogen atom or a C 1-C4 alkyl group, optionally substituted with one or more OH groups,
  • the groups R 2 which may be identical or different, preferably identical, denote linear or branched C1-C4 alkyl groups,
  • the groups R 3 which may be identical or different, preferably identical, denote linear or branched C 1-C4 alkyl groups,
  • R5 denotes a linear or branched Ci to C20, preferably C6-C20, alkyl group, optionally interrupted in its chain with an O or S atom or with an amido group or a carbonyl (CO) group,
  • the groups R 4 which may be identical or different, preferably identical, denote linear or branched C 1 -C4 alkyl groups.
  • the amino siliceous material used according to the invention as mattifying active agent may be obtained by hydrolysis and condensation, in the presence of water, of at least one, preferably one, aminoalkyltrialkoxysilane of formula (I) below:
  • Ri denotes a linear or branched, saturated or unsaturated Ci to Ce alkyl group, optionally interrupted with one or more groups NR, aryl and/or with one or more -O- atoms; a cyclic C 3 -C 5 hydrocarbon-based group, or denotes a C6-C 9 aryl or C6-C 9 aryloxy group, said radicals being substituted with an amino group NRR' or N + RR'R" with R, R', R" , which may be identical or different, denoting a hydrogen atom or a C i-C 4 alkyl group, optionally substituted with one or more OH groups,
  • the groups R 2 which may be identical or different, preferably identical, denote linear or branched C i-C 4 alkyl groups,
  • the groups R 3 which may be identical or different, preferably identical, denote linear or branched C i-C 4 alkyl groups,
  • R5 denotes a linear or branched Ci to C20, preferably C6-C20, alkyl group, optionally interrupted in its chain with an O or S atom or with an amido group or a carbonyl (CO) group, the groups R 4 , which may be identical or different, preferably identical, denote linear or branched C 1 -C4 alkyl groups.
  • the amino siliceous material used according to the invention as mattifying active agent may be obtained by reaction of at least one, preferably one, porous precipitated amorphous silica bearing surface hydroxyl groups with at least one, preferably one, aminoalkyltrialkoxysilane of formula (I) below:
  • Ri denotes a linear or branched, saturated or unsaturated Ci to Ce alkyl group, optionally interrupted with one or more groups NR, aryl and/or with one or more -O- atoms; a cyclic C 3 -C 5 hydrocarbon-based group, or denotes a C6-C 9 aryl or C6-C 9 aryloxy group, said radicals being substituted with an amino group NRR' or N + RR'R" with R, R', R" , which may be identical or different, denoting a hydrogen atom or a C i-C 4 alkyl group, optionally substituted with one or more OH groups,
  • the groups R 2 which may be identical or different, preferably identical, denote linear or branched C i-C 4 alkyl groups,
  • R5 denotes a linear or branched Ci to C 2 o, preferably C6-C 2 o, alkyl group, optionally interrupted in its chain with an O or S atom or with an amido group or a carbonyl (CO) group, and
  • the groups R 4 which may be identical or different, preferably identical, denote linear or branched C i-C 4 alkyl groups.
  • the amino siliceous material used according to the invention as mattifying active agent may be obtained by reaction of a porous precipitated amorphous silica bearing surface hydroxyl groups with at least one, preferably one, aminoalkyltrialkoxysilane of formula (I) below:
  • Ri denotes a linear or branched, saturated or unsaturated Ci to Ce alkyl group, optionally interrupted with one or more groups NR, aryl and/or with one or more -O- atoms; a cyclic C3-C5 hydrocarbon-based group, or denotes a C6-C 9 aryl or C6-C 9 aryloxy group, said radicals being substituted with an amino group NRR' or N + RR'R" with R, R', R" , which may be identical or different, denoting a hydrogen atom or a C 1-C4 alkyl group, optionally substituted with one or more OH groups,
  • the groups R 2 which may be identical or different, preferably identical, denote linear or branched C 1-C4 alkyl groups,
  • R5 denotes a linear or branched Ci to C 2 o, preferably C6-C 2 o, alkyl group, optionally interrupted in its chain with an O or S atom or with an amido group or a carbonyl (CO) group, and
  • the groups R 4 which may be identical or different, preferably identical, denote linear or branched C i-C 4 alkyl groups.
  • Ri represents a C 2 -C 4 hydrocarbon-based group substituted with a group NH 2 , NHR or NR' with R and R' denoting a linear or branched C i-C 4 alkyl group, and preferably a C 2 -C 4 hydrocarbon-based group, substituted with an NH 2 or OH group, said group Ri also possibly being substituted with an oxygen atom and a phenyl group, or RI represents a radical a C 2 -C 4 hydrocarbon-based group substituted with a tri(Ci - C6)alkylammonium.
  • RI denotes a -(CH 2 ) 3 -NH 2 radical.
  • RI preferably denotes a radical such as aminopropyl (-(CH 2 ) 3 -NH 2 ) or a radical chosen from radicals (a) to (d) below:
  • R 2 represents a linear alkyl group comprising from 1 to 4 carbon atoms and preferably an ethyl group.
  • the compound of formula (I) may be chosen from 3- aminopropyltriethoxy silane (APTES), 2- aminoethyltriethoxy silane (AETES), N-(2- aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, trimethyl[3-(triethoxysilyl)propyl]ammonium chloride, bis(2-hydroxyethyl)-3- aminopropyltriethoxysilane and more preferentially 3-aminopropyltriethoxysilane (APTES).
  • APTES 3- aminopropyltriethoxy silane
  • AETES 2- aminoethyltriethoxy silane
  • AETES 2- aminoethyltriethoxy silane
  • N-(2- aminoethyl)-3-aminopropyltriethoxysilane 3-(m-aminophenoxy)propyltrimethoxysi
  • R3 of compound (II) represents a linear alkyl group comprising from 1 to 4 carbon atoms and more particularly an ethyl group.
  • Compound (II) may be chosen from tetraethoxysilane (TEOS) and tetramethoxysilane (TMOS).
  • TEOS tetraethoxysilane
  • TMOS tetramethoxysilane
  • compound (II) is tetraethoxysilane (TEOS).
  • the amino siliceous material described previously may be obtained by hydrolysis and condensation of the compound(s) (I) and of the compound(s) (II) described previously or alternatively by reaction of the compound(s) (I) with at least one porous precipitated amorphous silica, and of at least one alkyltrialkoxysilane of formula (III) below:
  • R5 denotes a linear or branched Ci to C20, preferably C6-C20, alkyl group, optionally interrupted in its chain with an O or S atom or with an amido group or a carbonyl (CO) group, and
  • the groups R 4 which may be identical or different, preferably identical, denote linear or branched Ci-C 4 alkyl groups.
  • R 4 of compound (III) represents a linear alkyl group comprising from 1 to 4 carbon atoms and preferably an ethyl group.
  • R5 of compound (III) represents a Ce to C20 alkyl group and preferably an alkyl group chosen from n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n- hexadecyl and n-octadecyl.
  • Octyltrimethoxysilane, n-dodecyltrimethoxysilane, n- octadecyltrimethoxysilane, n-octyltriethoxysilane (OTES), n-dodecyltriethoxysilane or n- octadecyltriethoxysilane (ODTES), and mixtures thereof, may be used as compound (III).
  • compound (III) is chosen from n-dodecyltriethoxysilane, n- octadecyltriethoxysilane (ODTES) and n-octyltriethoxysilane (OTES).
  • compounds (II) and (I) are used in a compound (II)/compound (I) weight ratio ranging from 0.25 to 30 and preferably ranging from 0.5 to 25.
  • compounds (II) and (III) are used in a compound (II)/compound (III) weight ratio ranging from 0.25 to 30 and preferably ranging from 0.5 to 25.
  • the silica and compound (I) are used in a silica/compound (I) weight ratio ranging from 0.05 to 30 and preferably ranging from 0.1 to 25.
  • the silica and compound (III) are used in a silica/compound (III) weight ratio ranging from 1 to 40 and preferably ranging from 15 to 25.
  • the amino siliceous material is obtained by hydrolysis and condensation of the silanes described previously. This reaction corresponds to a sol-gel polymerization.
  • the sol-gel polymerization is performed in the presence of water to bring about the hydrolysis of the compound(s) (I) and of the compound(s) (II) and optionally of the compound(s) (III), followed by their condensation.
  • the sol-gel polymerization is performed in the presence of water to bring about the hydrolysis of a compound (I) and of a compound (II) and of a compound (III), followed by their condensation.
  • the polymerization may be performed in the presence of an acid catalyst, especially to accelerate the condensation reaction, for instance mineral acids such as hydrochloric acid, or organic acids such as acetic acid.
  • an acid catalyst especially to accelerate the condensation reaction
  • mineral acids such as hydrochloric acid
  • organic acids such as acetic acid.
  • the polymerization may be performed in the presence of a basic catalyst, for instance ammonia.
  • this amino siliceous material is performed according to chemical reactions known to those skilled in the art, triggered when the reagents are placed in contact with water and optionally with a catalyst, which has the effect of:
  • the siliceous material obtained is advantageously recovered according to the known techniques by filtration or centrifugation, and may especially be washed with water and/or ethanol, and then optionally dried or calcined. A siliceous material in powder form is thus obtained.
  • the concentration of the amino siliceous material preferably ranges from 0.1% to 100%, more preferentially from 1% to 70% and even more preferentially from 1% to 50% by weight relative to the total weight of the composition.
  • the amino siliceous material is obtained by reaction of the compound(s) (I) with at least one porous precipitated amorphous silica bearing surface hydroxyl groups, and optionally with at least one alkyltrialkoxysilane of formula (III).
  • This reaction is performed in an inert solvent, at a temperature ranging from 30°C to 200°C.
  • the amino siliceous material is in the form of porous particles of precipitated amorphous silica with a number-average particle size ranging from 1 to 25 ⁇ and preferably ranging from 1 to 20 ⁇ . Preferentially, they have a number-average size ranging from 1 to 10 ⁇ .
  • the term "precipitated amorphous silica” means a silica generally obtained by the action of an acid on a sodium silicate solution. Preferably, it is a spherical precipitated amorphous silica. This type of silica comprises silanol groups on its surface.
  • porous particles denotes particles having a structure comprising pores.
  • the porosity associated with the particle size is quantitatively characterized by their specific surface area.
  • the porous particles of the invention advantageously have a specific surface area measured according to the BET method of greater than or equal to 100 m 2 /g.
  • the BET (Brunauer-Emmett- Teller) method is a method that is well known to those skilled in the art. It is especially described by Brunauer, S. et al. Journal of the American Chemical Society, 1938, vol.60, Iss 2, page 309-319, and corresponds to international standard ISO 5794/1 (appendix D).
  • the specific surface area measured according to the BET method corresponds to the total specific surface area, i.e. it includes the surface area formed by the pores.
  • the silica particles have a specific surface area measured by BET ranging especially from 300 to 1000 m 2 /g. Preferentially, the specific surface area ranges from 400 to 900 m 2 /g.
  • Use may be made, as spherical porous silica particles, of those sold under the name Silica Beads SB-700 by the company Miyoshi or under the name Sunsphere® H51 or Sunsphere® H33 by the company Asahi Glass.
  • inert solvent used in reaction ii use may be made of toluene, alkanes such as pentane, cyclopentane, hexane and cyclohexane, benzene, 1,4-dioxane, chloroform, dichloromethane, tetrahydrofuran, esters such as ethyl acetate and butyl acetate, formamides such as ⁇ , ⁇ -dimethylformamide (DMF), acetonitrile, dimethyl sulfoxide (DMSO), propylene carbonate, ketones such as methyl isobutyl ketone (MEK) and acetone, xylene, N-methylpyrrolidone or l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)- pyrimidinone (DMPU).
  • alkanes such as pentane, cyclopentane, hexane and cyclohexane
  • the inert solvent used is toluene.
  • the reaction may be performed for a time ranging from 15 minutes to 2 days.
  • the reaction is performed at a temperature ranging from 30 to
  • the grafting reaction ii performed may be represented schematically in the following manner:
  • the silica obtained thus comprises groups -(O -) 3 / 2 Si-Ri
  • test composition is spread at a rate of 10 mg/cm 2 onto isolated strata cornea pretreated with a mixture of sebum and sweat known to give shiny skin.
  • the sheen of the surfaces is measured with a Tri-Glossmaster glossmeter from the constructor Sheen at an angle of 60° and 1 to 2 minutes after depositing the test composition.
  • the mattifying fillers used according to the invention are those which preferably give, at a content of 1% in a cosmetic composition, a reduction in sheen of greater than 30% and preferably less than 40%.
  • compositions may comprise an additional mattifying filler.
  • fillers should be understood as meaning colourless or white, mineral or synthetic particles of any shape, which are insoluble and dispersed in the medium of the composition irrespective of the temperature at which the composition is manufactured.
  • these mattifying fillers may be chosen, for example, from silicas, clays and silicate derivatives.
  • the additional mattifying fillers represent from 0.05% to 30% by weight, from 0.1% to 30% by weight, preferably from 0.1% to 20% by weight, better still from 0.2% to 10% by weight and more preferably from 0.5% to 5% by weight and from 1.5% to 5% by weight relative to the total weight of the composition.
  • compositions according to the invention may comprise at least one aqueous phase. They are especially formulated as aqueous lotions or as water-in-oil or oil- in-water emulsions or multiple emulsions (oil-in-water-in-oil or water-in-oil-in-water triple emulsion), gels or foams.
  • the aqueous phase of said compositions contains water and generally other water-soluble or water- miscible solvents.
  • the water-soluble or water- miscible solvents comprise short chain, for example C2-C4, monoalcohols, such as ethanol or isopropanol; diols or polyols, for instance ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol.
  • Propylene glycol and glycerol, 1,3-propanediol, and ethanol will be used more particularly.
  • composition according to the invention preferably has a pH ranging from 3 to 9, depending on the support chosen.
  • composition in emulsion form may also comprise at least one surfactant.
  • the total amount of surfactants in the composition will preferably be, in the composition according to the invention, at active material contents ranging from 0.1% to 10% by weight and more particularly from 0.5% to 6% by weight, relative to the total weight of the composition.
  • compositions according to the invention may contain at least one water- immiscible organic liquid phase, known as a fatty phase.
  • This phase generally comprises one or more hydrophobic compounds which render said phase water-immiscible.
  • Said phase is liquid (in the absence of structuring agent) at room temperature (20-25°C).
  • the water-immiscible organic liquid phase in accordance with the invention generally comprises at least one volatile oil and/or one non-volatile oil, optionally non- liquid fatty substances and optionally at least one structuring agent.
  • oil means a fatty substance that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg, i.e. 10 5 Pa).
  • the oil may be volatile or nonvolatile.
  • volatile oil means an oil that is capable of evaporating on contact with the skin or the keratin fibre in less than one hour, at room temperature and atmospheric pressure.
  • volatile oils of the invention are volatile cosmetic oils that are liquid at room temperature, with a non-zero vapour pressure, at room temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10 3 to 300 mmHg), in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • non-volatile oil is intended to mean an oil that remains on the skin or the keratin fibre at ambient temperature and atmospheric pressure for at least several hours, and that in particular has a vapour pressure of less than 10 "3 mmHg (0.13 Pa).
  • the oil may be chosen from any physiologically acceptable oil and in particular cosmetically acceptable oil, especially mineral, animal, plant or synthetic oils; in particular volatile or non-volatile hydrocarbon-based oils and/or silicone oils and/or fluoro oils, and mixtures thereof.
  • hydrocarbon-based oil means an oil mainly comprising carbon and hydrogen atoms and optionally one or more functions chosen from hydroxyl, ester, ether and carboxylic functions.
  • the oil has a viscosity of from 0.5 to 100 000 mPa.s, preferably from 50 to 50 000 mPa.s and more preferably from 100 to 300 000 mPa.s.
  • volatile oils that may be used in the invention, mention may be made of:
  • hydrocarbon-based oils chosen from hydrocarbon-based oils containing from 8 to 16 carbon atoms, and especially C8-C16 isoalkanes of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane and isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, branched C8-C16 esters and isohexyl neopentanoate, and mixtures thereof.
  • C8-C16 isoalkanes of petroleum origin also known as isoparaffins
  • isododecane also known as 2,2,4,4,6-pentamethylheptane
  • isodecane and isohexadecane for example the oils sold under the trade names Isopar or Permethyl, branched C8-C16 esters and isohexyl neopentanoate, and mixtures thereof.
  • Use may also be made of other volatile hydrocarbon-based oils, such as petroleum distillates, in particular those sold under the name Shell Solt by the company Shell; and volatile linear alkanes, such as those described in Patent Application DE10 2008 012 457 from the company Cognis;
  • volatile silicones for instance linear or cyclic volatile silicone oils, in particular those with a viscosity of ⁇ 8 centistokes (8 x 10 "6 m 2 /s), and containing in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms;
  • non-volatile oils that may be used in the invention, mention may be made of:
  • hydrocarbon-based plant oils such as liquid triglycerides of fatty acids of 4 to 24 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or wheatgerm oil, olive oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil, musk rose oil, sunflower oil, corn oil, soybean oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba
  • esters especially of fatty acids, for instance the oils of formula R1COOR2 in which P i represents a linear or branched higher fatty acid residue containing from 1 to 40 carbon atoms and R2 represents a hydrocarbon-based chain, which is especially branched, containing from 1 to 40 carbon atoms, with Ri + R 2 > 10, for instance purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, isopropyl palmitate, C12-C15 alcohol benzoates, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2- ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate or tridecyl trimellitate; alcohol or polyalcohol oc
  • - fatty alcohols that are liquid at room temperature, containing a branched and/or unsaturated carbon chain containing from 12 to 26 carbon atoms, for instance octyldodecanol, isostearyl alcohol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol or oleyl alcohol;
  • fluoro oils which are optionally partially hydrocarbon-based and/or silicone-based, for example fluoro silicone oils, fluoropolyethers or fluorinated silicones, such as described in document EP-A-847 752;
  • silicone oils such as non-volatile linear or cyclic polydimethylsiloxanes (PDMSs); polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups which are pendent or at the end of the silicone chain, which groups have from 2 to 24 carbon atoms; or phenylated silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphenyl dimethicones, diphenyl(methyldiphenyl)trisiloxanes or (2-phenylethyl)trimethylsiloxysilicates, and - mixtures thereof.
  • PDMSs non-volatile linear or cyclic polydimethylsiloxanes
  • phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)dipheny
  • the cosmetic compositions according to the invention may also comprise cosmetic adjuvants chosen from emollients, antioxidants, opacifiers, stabilizers, moisturizers, vitamins, bactericides, preserving agents, polymers, fragrances, a structuring agent for a fatty phase, in particular chosen from waxes, pasty compounds, mineral or organic lipophilic gelling agents; organic or mineral fillers; thickeners or suspending agents, propellants or any other ingredient normally used in cosmetics for this type of application.
  • cosmetic adjuvants chosen from emollients, antioxidants, opacifiers, stabilizers, moisturizers, vitamins, bactericides, preserving agents, polymers, fragrances, a structuring agent for a fatty phase, in particular chosen from waxes, pasty compounds, mineral or organic lipophilic gelling agents; organic or mineral fillers; thickeners or suspending agents, propellants or any other ingredient normally used in cosmetics for this type of application.
  • the amounts of these various constituents that may be present in the cosmetic composition according to the invention are those conventionally used in mattifying compositions.
  • Example 1 Amphiphilic silica - Synthesis of TEOS@APTES:OTES (1: 1: 1)
  • the precipitate was washed and centrifuged three times with 200 mL of ethanol, then twice with 300 mL of distilled water and finally dried under vacuum at 80°C for 24 hours. 7.4 g of a white powder in the form of particles were obtained.
  • the precipitate obtained was washed with 200 ml of ethanol and then centrifuged twice with 200 mL of ethanol and twice with 200 mL of distilled water and finally dried under vacuum at 80°C for 24 hours. 4.2 g of a white powder in the form of particles were obtained.
  • the precipitate obtained was washed with 200 ml of ethanol and then centrifuged twice with 200 mL of ethanol and twice with 200 mL of distilled water and finally dried under vacuum at 80°C for 24 hours. 2.8 g of a white powder in the form of particles were obtained.
  • Example 7 Cationic silica - Synthesis of Si@APTES (1:5)
  • a mixture of 10 g of amorphous silica microspheres (particle size: 5 microns; Sunsphere H 51 from AGC SI-TECH) and 50 g of 3-aminopropyltriethoxysilane in 300 ml of toluene was refluxed for 6 hours in a three-necked round-bottomed flask equipped with a condenser and a thermometer, and then left to cool overnight.
  • the reaction mixture was poured onto 300 mL of ethanol. The mixture was left without stirring for 2 hours and then centrifuged at 4000 rpm for 4 minutes.
  • the precipitate obtained was washed in 200 ml of ethanol and then centrifuged twice with 200 mL of ethanol and twice with 200 mL of distilled water and finally dried under vacuum at 80°C for 24 hours. 4 g of a white powder in the form of particles were obtained.
  • a mixture of 8 g of amorphous silica microspheres (particle size: 5 microns; Sunsphere H 51 from AGC SI- TECH) and 0.8 g of 3-aminopropyltriethoxysilane in 300 ml of toluene was refluxed for 8 hours in a three-necked round-bottomed flask equipped with a condenser and a thermometer, and then left to cool overnight.
  • the reaction mixture was poured onto 300 mL of ethanol. The mixture was left without stirring for 1 hour and then centrifuged at 4000 rpm for 4 minutes.
  • the precipitate obtained was washed in 200 ml of ethanol and then centrifuged twice with 200 mL of ethanol and twice with 300 mL of distilled water and finally dried under vacuum at 80°C for 24 hours. 6.2 g of a white powder in the form of particles were obtained.
  • the reaction mixture was poured onto 300 mL of ethanol. The mixture was left without stirring for 1 hour and then centrifuged at 4000 rpm for 4 minutes.
  • composition of the artificial sebum (amounts indicated as mass percentages):
  • composition of the artificial sweat (amounts indicated as mass percentages):
  • the film is then left to dry in the open air for 30 minutes.
  • Each compound to be evaluated is dispersed in ethanol and stirred using an ultrasonic bath for 15 minutes in order to obtain dispersions, and then deposited in dispersion form at 1% by mass in ethanol onto the dry hydrolipid film at a rate of 2 ⁇ 2 .
  • the sheen of the surfaces is measured with a Tri-Glossmaster glossmeter from the constructor Sheen at an angle of 60° and 1 to 2 minutes after depositing the dispersion.
  • the variation of the sheen is calculated according to the following formula:
  • the sheen of the skin was significantly reduced with the particles according to Exampli 4 and 8 when compared with the example outside the invention.
  • composition allows the sheen to be reduced when applied to the face.

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Abstract

La présente invention concerne l'utilisation cosmétique, en tant qu'agent actif matifiant d'un matériau siliceux comprenant au moins une amine.
PCT/EP2015/064738 2014-06-30 2015-06-29 Utilisation cosmétique, en tant qu'agent actif matifiant, d'un matériau siliceux cationique ou amphiphile WO2016001168A1 (fr)

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FR1456189A FR3022777B1 (fr) 2014-06-30 2014-06-30 Utilisation cosmetique comme actif matifiant d'un materiau silicie cationique ou amphiphile.

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2251594A1 (fr) * 1973-11-16 1975-06-13 Merck Patent Gmbh
WO2001052618A2 (fr) * 2000-01-19 2001-07-26 Bridgestone Corporation Silice stabilisee et methodes de production et d'utilisation associees
US20060154072A1 (en) * 2001-11-16 2006-07-13 David Schlossman Organosilicon treated cosmetic powders, their production and use
EP2266532A2 (fr) * 2009-06-22 2010-12-29 Shin-Etsu Chemical Co., Ltd. Particules composites, leur procédé de préparation et composition cosmétique
WO2013160362A1 (fr) * 2012-04-26 2013-10-31 L'oreal Composition cosmétique comprenant des charges matifiantes et un silane

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2251594A1 (fr) * 1973-11-16 1975-06-13 Merck Patent Gmbh
WO2001052618A2 (fr) * 2000-01-19 2001-07-26 Bridgestone Corporation Silice stabilisee et methodes de production et d'utilisation associees
US20060154072A1 (en) * 2001-11-16 2006-07-13 David Schlossman Organosilicon treated cosmetic powders, their production and use
EP2266532A2 (fr) * 2009-06-22 2010-12-29 Shin-Etsu Chemical Co., Ltd. Particules composites, leur procédé de préparation et composition cosmétique
WO2013160362A1 (fr) * 2012-04-26 2013-10-31 L'oreal Composition cosmétique comprenant des charges matifiantes et un silane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SRISUDA SAE-UNG ET AL: "One-Pot Synthesis of Organic-Inorganic Hybrid Mesoporous Materials for the Adsorption of Formaldehyde Vapor", ENVIRONMENTAL ENGINEERING SCIENCE, vol. 25, no. 3, 1 April 2008 (2008-04-01), pages 397 - 406, XP055111538, ISSN: 1092-8758, DOI: 10.1089/ees.2007.0011 *

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