WO2011161020A1 - Composition cosmétique comprenant au moins un polysaccharide oxydé non cationique et une huile, préférentiellement une huile non polaire - Google Patents

Composition cosmétique comprenant au moins un polysaccharide oxydé non cationique et une huile, préférentiellement une huile non polaire Download PDF

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Publication number
WO2011161020A1
WO2011161020A1 PCT/EP2011/060142 EP2011060142W WO2011161020A1 WO 2011161020 A1 WO2011161020 A1 WO 2011161020A1 EP 2011060142 W EP2011060142 W EP 2011060142W WO 2011161020 A1 WO2011161020 A1 WO 2011161020A1
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Prior art keywords
oil
meq
carbon atoms
polysaccharide
esters
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PCT/EP2011/060142
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English (en)
Inventor
Gérard Malle
Michel Philippe
Charlotte Feltin
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L'oreal
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Publication of WO2011161020A1 publication Critical patent/WO2011161020A1/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
    • A61K8/18—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
    • 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
    • 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
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • 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
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings

Definitions

  • Cosmetic composition comprising at least one noncationic oxidized polysaccharide and one oil, preferably a polar oil
  • the field of the invention relates to making up and/or caring for keratin materials.
  • keratin materials' is understood to mean the skin and its integuments, and especially the skin, the lips, the eyelashes and/or the nails.
  • Cosmetic compositions are sought, in particular in the form of emulsions, especially oil-in- water emulsions, which have good cosmetic properties in terms of texture and comfort on application, and which are stable.
  • the formulation of the cosmetic compositions, in particular when they are makeup compositions, should especially take into account the dispersion of the dyestuffs that they contain and the stability of said compositions.
  • noncationic oxidized polysaccharides in care and/or makeup cosmetic compositions, especially as emulsifiers, for improving the formulation of said compositions and/or the cosmetic texture properties thereof.
  • said noncationic polysaccharides according to the invention have a better ability to be formulated (especially limited solubility and limited compatibility in the cosmetic media) than the unoxidized native forms, in particular for the families having a higher molecular weight than starches and cellulose.
  • the invention thus relates in particular to a cosmetic composition for caring for and/or making up keratin materials comprising, in a physiologically acceptable medium, at least:
  • P represents a polysaccharide chain constituted of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms
  • m is such that the content of aldehyde groups (CHO) in the polysaccharide lies within the interval ranging from 0.05 to 6 meq/g, especially from 0.07 to 3, better still from 0.09 to 2 meq/g and even better still from 0.1 to 1 meq/g
  • n is such that the content of carboxyl groups (COOH) in the polysaccharide lies within the interval ranging from 0.05 to 0.9 meq/g, especially from 0.07 to 0.5 meq/g, better still from 0.9 to 0.4 meq/g and even better still from 0.1 to 0.3 meq/g
  • COOH carboxyl groups
  • meq/g is understood to mean the number of millimoles of CO, or respectively of COOH, contained in 1 g of polysaccharide.
  • composition of the invention comprises, in a physiologically acceptable medium, at least:
  • one or more noncationic oxidized polysaccharides comprising a polysaccharide chain P constituted of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms, and characterized by the presence of at least two separate majority populations of oxidized polysaccharides, having a weight-average molecular weight ranging from 500 to 15 000 000, and better still between 800 and 10 000 000 and even better still between 1000 and 1 000 000, and (ii) at least one oil, preferably a polar oil.
  • the oxidized polysaccharides according to the invention are characterized by the presence of at least two separate majority populations of polysaccharides having different average molecular weights, the majority population being that of higher average molecular weight.
  • the oxidized polysaccharides according to the invention advantageously comprise at least one first population having an average molecular weight ranging from 500 to 10 000, in particular from 1000 to 5000 and at least one second, majority population having an average molecular weight greater than 10 000 and preferably ranging from 10 000 to 300 000, advantageously from 15 000 to 100 000 and better still from 20 000 to 60 000.
  • the characterization of these populations may especially be carried out by 2D DOSY NMR, which simultaneously allows the number of molecular components of a solution to be identified and the sizes of the molecules or aggregates present in a mixture to be determined.
  • the care and/or makeup composition according to the invention could also comprise at least one particulate material, especially chosen from fillers and/or pigments.
  • the content of particulate material could advantageously range from 0.1 to 70% by weight, especially from 1 to 50% by weight, and in particular for makeup compositions, the content could range from 5 to 40% by weight, relative to the total weight of said composition.
  • Polymers of oxidized polysaccharide type and in particular polymers corresponding to the following definition prove to perform particularly well.
  • the cosmetic composition in accordance with the invention comprises, in a cosmetically acceptable medium, at least one noncationic oxidized polysaccharide of formula (I) and/or the organic or inorganic carboxylic acid salts thereof:
  • P represents a polysaccharide chain constituted of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms
  • m is such that the content of aldehyde groups (CHO) in the polysaccharide lies within the interval ranging from 0.05 to 6 meq/g, especially from 0.07 to 3, better still from 0.09 to 2 meq/g and even better still from 0.1 to 1 meq/g
  • n is such that the content of carboxyl groups (COOH) in the polysaccharide lies within the interval ranging from 0.05 to 0.9 meq/g, especially from 0.07 to 0.5 meq/g, better still from 0.9 to 0.4 meq/g and even better still from 0.1 to 0.3 meq/g.
  • meq/g is understood to mean the number of millimoles of CO contained in 1 g of polysaccharide.
  • the amount of CO in g per 100 g of polysaccharide is obtained by multiplying the number of meq/g by 2.8.
  • the term "meq/g” is understood to mean the number of millimoles of COOH contained in 1 g of polysaccharide.
  • the amount of COOH in g per 100 g of polysaccharide is obtained by multiplying the number of meq/g by 4.5.
  • the m/n ratio representing the content of aldehydes (CHO)/content of carboxyls (COOH) ratio, is between 0.9 and 14, especially between 1 and 7, preferably between 1.1 and 5 and better still between 1.2 and 4.
  • the content of aldehyde groups (CHO) in the polysaccharides according to the invention is especially determined by back titration with hydrochloric acid, in the presence of hydroxylamine.
  • the hydroxylamine is added to the oxidized polysaccharide and reacts with the carbonyl function to form an oxime.
  • the excess hydroxylamine is then titrated with hydrochloric acid.
  • the content of carboxyl groups (COOH) in the polysaccharides according to the invention is especially determined by direct titration with sodium hydroxide using pH-metry.
  • the CHO and COOH groups may be obtained during the oxidation of certain carbon atoms, for example at the C2, C3 or C6 position of a saccharide unit having 6 carbon atoms.
  • the polysaccharide chain P before and after oxidation, preferably has a weight-average molecular weight ranging from 500 to 15 000 000, and better still between 800 and 10 000 000 and even better still between 1000 and 1 000 000.
  • composition of the invention comprises, in a physiologically acceptable medium, at least:
  • one or more noncationic oxidized polysaccharides comprising a polysaccharide chain P constituted of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms, and characterized by the presence of at least two separate majority populations of oxidized polysaccharides, having a weight-average molecular weight ranging from 500 to 15 000 000, and better still between 800 and 10 000 000 and even better still between 1000 and 1 000 000,
  • the oxidized polysaccharides according to the invention are characterized by the presence of at least two separate majority populations of polysaccharides having different average molecular weights, the majority population being that of higher average molecular weight.
  • the oxidized polysaccharides according to the invention advantageously comprise at least one first population having an average molecular weight ranging from 500 to 10 000, in particular from 1000 to 5000 and at least one second, majority population having an average molecular weight greater than 10 000 and preferably ranging from 10 000 to 300 000, advantageously from 15 000 to 100 000 and better still from 20 000 to 60 000.
  • the characterization of these populations may especially be carried out by 2D DOSY NMR, which simultaneously allows the number of molecular components of a solution to be identified and the sizes of the molecules or aggregates present in a mixture to be determined.
  • the polysaccharide chain, represented by P, is preferably chosen from:
  • fructans or fructosans in particular inulin and graminan
  • glucans in particular starch, carboxymethyl starch, pectin, amylopectin, amylose, cellulose and the alkyl, hydroxyalkyl or carboxyalkyl derivatives thereof, such as carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose and methyl cellulose; curdlan, dextran or pullulan; - galactans, in particular agar-agar and carrageenans;
  • hemicelluloses in particular arabans, xylans, hexosans and polyuronides;
  • mannans guars, alginates, xanthans and pentosans.
  • the oxidation may be carried out according to a process described in the article "Water soluble oxidized starches by peroxide reactive extrusion” by R.E. Wing and J.L. Willett, Industrial Crops and Products, 7, 1997, pages 45-52.
  • the oxidizing agents used to carry out the oxidation of the polysaccharides according to the invention preferably belong to the families of peroxides, such as for example perborates, percarbonates, peracetic acid, alkyl peroxides or else hydrogen peroxide commonly referred to as aqueous hydrogen peroxide solution and to the families of N- oxides, such as for example 2,2,6,6-tetramethylpiperidine-1 -oxyl commonly referred to as TEMPO and also 4-hydroxy-TEMPO or 4-acetamido-TEMPO derivatives or else TEMPO derivatives immobilized on polymers such as those described by R. Ciriminna and M. Pagliaro in "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives", Organic Process Research & Development ⁇ : 245 (2010).
  • peroxides such as for example perborates, percarbonates, peracetic acid, alkyl peroxides or else hydrogen peroxide commonly referred to as a
  • aqueous hydrogen peroxide solution is particularly preferred in so far as it is inexpensive, easy to use and does not produce troublesome byproducts.
  • the oxidation of the C6 carbon which converts the hydroxymethyl group into a carboxyl group, may be represented by the following reaction scheme:
  • glycolic oxidation which converts the C2 and C3 hydroxyl groups into aldehydes, and/or into carboxylic acids, by ring opening and oxidation, may be represented by the following reaction scheme:
  • glycolic oxidation which converts the C2 and C3 hydroxyl groups into aldehydes, and/or into carboxylic acids, by ring opening and oxidation, may also be represented by the following reaction scheme:
  • the temperature of the reaction is generally between 10°C and 250°C, preferably between 30 and 160°C.
  • the reaction is preferably carried out by maintaining the pH of the reaction medium at a value between 3 and 12, more particularly between 5 and 9.
  • the process may be implemented for any polysaccharide.
  • said oxidized polysaccharide is a potato starch.
  • the polysaccharide chain P is obtained by oxidation of cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, methyl cellulose, starch, amylose, carboxymethyl starch, amylose, inulin, guar, xanthan, carrageenan, dextran or scleroglucan.
  • the polysaccharide chain P represents a polymer chain resulting from cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, methyl cellulose, starch, carboxymethyl starch, amylose, inulin, guar, xanthan, carrageenan, dextran or scleroglucan.
  • the polysaccharide chain P represents a starch, or an amylose, such as a maize amylose, a potato starch, a wheat starch or a rice starch.
  • the polysaccharide chain P represents a potato starch.
  • the composition of the invention comprises at least one noncationic oxidized polysaccharide in the invention corresponding to the formula (I):
  • P represents a polymer chain resulting from cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, methyl cellulose, starch, carboxymethyl starch, amylose, inulin, guar, xanthan, carrageenan, dextran or scleroglucan
  • m is such that the content of aldehyde groups (CHO) in the polysaccharide lies within the interval ranging from 0.05 to 6 meq/g, especially from 0.07 to 3, better still from 0.09 to 2 meq/g and even better still from 0.1 to 1 meq/g
  • n is such that the content of carboxyl groups (COOH) in the polysaccharide lies within the interval ranging from 0.05 to 0.9 meq/g, especially from 0.07 to 0.5 meq/g, better still from 0.9 to 0.4 meq/g and even better still from 0.1 to 0.3 meq/g.
  • composition of the invention comprises at least one noncationic oxidized polysaccharide of formula (I) chosen from those for which:
  • P represents a starch, or an amylose, such as a maize amylose, a potato starch, a wheat starch or a rice starch
  • m is such that the content of aldehyde groups (CHO) in the polysaccharide lies within the interval ranging from 0.05 to 6 meq/g, especially from 0.07 to 3, better still from 0.09 to 2 meq/g and even better still from 0.1 to 1 meq/g
  • n is such that the content of carboxyl groups (COOH) in the polysaccharide lies within the interval ranging from 0.05 to 0.9 meq/g, especially from 0.07 to 0.5 meq/g, better still from 0.9 to 0.4 meq/g and even better still from 0.1 to 0.3 meq/g.
  • composition of the invention comprises a noncationic oxidized polysaccharide of formula (I) chosen from those for which:
  • P represents a starch
  • m is such that the content of aldehyde groups (CHO) in the polysaccharide lies within the interval ranging from 0.05 to 6 meq/g, especially from 0.07 to 3, better still from 0.09 to 2 meq/g and even better still from 0.1 to 1 meq/g
  • n is such that the content of carboxyl groups (COOH) in the polysaccharide lies within the interval ranging from 0.05 to 0.9 meq/g, especially from 0.07 to 0.5 meq/g, better still from 0.9 to 0.4 meq/g and even better still from 0.1 to 0.3 meq/g.
  • the composition of the invention comprises a noncationic oxidized polysaccharide of formula (I) chosen from those for which:
  • P represents a potato starch
  • m is such that the content of aldehyde groups (CHO) in the polysaccharide lies within the interval ranging from 0.1 to 1 meq/g
  • n is such that the content of carboxyl groups (COOH) in the polysaccharide lies within the interval ranging from 0.1 to 0.3 meq/g.
  • the noncationic oxidized polysaccharide (i) according to the invention is generally present in the composition in an amount ranging from 1 to 30% by weight (of active material) relative to the total weight of the composition, preferably from 2 to 20% by weight and better still from 3 to 10% by weight, relative to the total weight of the composition.
  • composition according to the invention comprises at least one oil, preferably a polar oil.
  • a polar oil is a hydrocarbon-based, non-volatile oil.
  • the polar oil according to the invention comprises at least one unsaturated group.
  • saturated group is understood according to the invention to mean that the hydrocarbon-based chain of said oil comprises at least one carbon-carbon double bond or triple bond.
  • non-volatile oil means an oil with a vapour pressure of less than 0.13 Pa.
  • hydrocarbon-based oil means an oil mainly containing hydrogen and carbon atoms.
  • polar oil means an oil whose solubility parameter at 25°C, 5a, is other than 0 (J/cm 3 ) 1 ' 2 .
  • the parameters ⁇ ⁇ , 5 h , 5 D and 5 a are expressed in (J/cm 3 ) 1 ⁇ 2 .
  • the preferred polar non-volatile oils have a solubility parameter at 25°C, 5a, above 2, or even above 3 (J/cm 3 ) 1 ' 2 .
  • hydrocarbon-based oils of plant origin in particular triglycerides constituted of fatty acid esters of glycerol, in particular in which the fatty acids may have chain lengths ranging from C 4 to C 36 , and especially from Ci 8 to C 3 6, these oils possibly being linear or weakly branched, and unsaturated, in particular jojoba oil, meadowfoam oil, olive oil, sesame oil, castor oil, and mixtures thereof, or alternatively 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, synthetic esters, for instance oils of formula RiCOOR 2 , in which R-i represents a linear or branched, preferably linear or weakly branched, fatty acid residue containing from 1 to 40 carbon atoms and preferably comprising at least one unsaturated group, and R 2 represents a
  • the esters may in particular be chosen from fatty acid esters of alcohol, such as, for example: cetostearyl octanoate, isopropyl alcohol esters, such as isopropyl myristate, isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate, isopropyl isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, diisopropyl adipate, heptanoates, and especially isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, for instance propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, 2-
  • polyol esters and pentaerythritol esters for instance dipentaerythritol tetrahydroxystearate/tetraisostearate or pentaerythrityl tetraisostearate
  • polyol esters and pentaerythritol esters for instance dipentaerythritol tetrahydroxystearate/tetraisostearate or pentaerythrityl tetraisostearate
  • the polar, hydrocarbon-based, non-volatile oils (ii) used according to the invention comprise linear or weakly branched fatty acid chains that have at least one unsaturated group.
  • the polar, non-volatile oils used according to the invention comprise linear or weakly branched fatty acid chains that have at least one unsaturated group, preferably at least two unsaturated groups.
  • the polar, non-volatile oils used according to the invention comprise linear fatty acid chains that have at least two unsaturated groups.
  • a polar, hydrocarbon-based, non-volatile oil (ii) chosen from:
  • hydrocarbon-based oils of plant origin in particular triglycerides constituted of fatty acid esters of glycerol, in particular in which the fatty acids may have chain lengths ranging from C 4 to C 36 , and especially from Ci 8 to C 3 6, these oils possibly being linear or weakly branched, and unsaturated, in particular jojoba oil, meadowfoam oil, olive oil, sesame oil, castor oil, and mixtures thereof, or alternatively caprylic/capric acid triglycerides, for instance those sold by the company STEARINERIES DUBOIS or those sold under the names
  • hydrocarbon- based, non-volatile oils chosen from the triglycerides constituted of fatty acid esters of glycerol, in which the fatty acids may have chain lengths ranging from C 4 to C 36 , and especially from Ci 8 to C 3 6, these oils being linear or weakly branched, and unsaturated, such as jojoba oil, meadowfoam oil, olive oil, sesame oil, castor oil, and mixtures thereof, or alternatively 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 oil is used.
  • castor oil is used.
  • sesame oil is used.
  • 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.
  • pentaerythrityl tetraisostearate sold under the name CRODAMOL PTIS-LQ by the company CRODA.
  • the content of polar oil(s) according to the invention may range from 1 % to 70% by weight, preferably ranging from 2% to 50% by weight and preferentially ranging from 5% to 35% by weight relative to the total weight of the composition.
  • a person skilled in the art will adjust the contents of water, oil and noncationic oxidized polysaccharide depending in particular on the nature of the oil (polarity, unsaturated groups, branching), and on the viscosity of said oxidized polysaccharide.
  • a water/oil ratio in particular a water/polar oil(s) ratio, of 80/20 to 20/80, advantageously a ratio of 70/30 to 30/70 and especially of 70/30 to 50/50 with a content of oxidized polysaccharides ranging from 1 to 30% by weight relative to the total weight of the composition, preferably from 2 to 20% by weight and better still from 3 to 10% by weight, relative to the total weight of the composition.
  • physiologically acceptable medium is intended to denote a medium that is particularly suitable for applying a composition of the invention to the skin, the eyelashes, the nails or the lips.
  • the physiologically acceptable medium is generally adapted to the nature of the support onto which the composition is to be applied, and also to the form in which the composition is to be packaged.
  • the composition may be in various forms, as a function of its intended use.
  • the cosmetic composition may thus be in any galenic form normally used for topical application and especially in the form of an oily or aqueous solution, an oily or aqueous gel, an oil-in- water, water-in-oil, wax-in-water or water-in-wax emulsion, a multiple emulsion, or a dispersion of oil in water by means of vesicles located at the oil/water interface.
  • the composition may be in the form of a cast product, especially a stick in the case of a lipstick or of a lipcare product; or in the form of a cast foundation or in the form of a solid emulsion.
  • composition may also be in various other forms, for example a more or less viscous liquid, a gel or a paste.
  • composition may also be in the form of a semi-solid or a solid, for example a cake to be moistened at the time of use, so as to allow it to be broken down.
  • the cosmetic composition may constitute, inter alia, a care composition, a lipstick, a liquid gloss, a lipstick paste, a face powder, a lip pencil, a solid or fluid foundation, a concealer or eye contour product, an eyeliner, a mascara, a nail varnish, an eyeshadow, a body makeup product or else a suncare product or skin colouring product.
  • another subject of the invention is a liquid or semi-solid lipstick.
  • Another subject of the invention is a foundation.
  • Another subject of the invention is a nail varnish.
  • Another subject of the invention is a mascara.
  • the composition according to the invention generally comprises an aqueous phase.
  • the aqueous phase comprises water.
  • a water that is suitable for use in the invention may be a floral water such as cornflower water and/or a mineral water such as Vittel water, Lucas water or La Roche Posay water and/or a spring water.
  • the aqueous phase may also comprise organic solvents that are water-miscible (at room temperature: 25°C), for instance monoalcohols containing from 2 to 6 carbon atoms, such as ethanol or isopropanol; polyols especially containing from 2 to 20 carbon atoms, preferably containing from 2 to 10 carbon atoms and preferentially containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1 ,3-propanediol, butylene glycol, 1 ,4- butanediol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; glycol ethers (especially containing from 3 to 16 carbon atoms) such as mono-, di- or tripropylene glycol (CrC 4 )alkyl ethers, mono-, di- or triethylene glycol (CrC 4 )alkyl ethers, and mixtures thereof.
  • the aqueous phase may also comprise stabilizers, for example sodium chloride, magnesium dichloride or magnesium sulphate.
  • the aqueous phase may also comprise any water-soluble or water-dispersible compound that is compatible with an aqueous phase, such as gelling agents, film-forming polymers, thickeners or surfactants, and mixtures thereof.
  • a composition of the invention may comprise an aqueous phase in a content ranging from 1 % to 80% by weight, especially from 5% to 70% and more particularly from 10% to 60% by weight relative to the total weight of the composition.
  • a cosmetic composition in accordance with the present invention comprises at least one liquid and/or solid fatty phase.
  • composition of the invention comprises at least one liquid fatty phase comprising at least the polar oil described previously and optionally at least one additional oil as mentioned below.
  • oil means any fatty substance that is in liquid form at room temperature (20-25°C) and at atmospheric pressure.
  • a composition of the invention may comprise a liquid fatty phase in a content ranging from 1 % to 90%, in particular from 5% to 80%, in particular from 10% to 70% and more particularly from 20% to 50% by weight relative to the total weight of the composition.
  • 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 especially be of animal, plant, mineral or synthetic origin.
  • volatile oil means an oil (or non-aqueous medium) capable of evaporating on contact with the skin in less than one hour at room temperature and atmospheric pressure.
  • the volatile oil is a volatile cosmetic oil, which is liquid at room temperature, especially having a non-zero vapour pressure, at room temperature and atmospheric pressure, in particular having a vapour pressure ranging from 0.13 Pa to 40 000 Pa (10 "3 to 300 mmHg), preferably ranging from 1 .3 Pa to 13 000 Pa (0.01 to 100 mmHg), and preferentially ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • non-volatile oil means an oil with a vapour pressure of less than 0.13 Pa.
  • silicon oil means an oil comprising at least one silicon atom, and especially at least one Si-0 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, sulphur and/or phosphorus atoms, for example in the form of hydroxyl or acid radicals.
  • composition may also comprise at least one fatty phase structuring agent and/or one aqueous phase gelling agent and/or thickener.
  • a composition according to the invention may also comprise at least one colouring or non-colouring particulate material, in particular chosen from fillers and/or pulverulent dyestuffs.
  • the particulate material(s) may be present in a content ranging advantageously from 0.1 to 70% by weight, especially from 1 to 50% by weight, and in particular for makeup compositions, a content ranging from 5 to 40% by weight, relative to the total weight of said composition.
  • composition in accordance with the invention may comprise at least one filler, of organic or inorganic nature, which makes it possible in particular to confer thereon additional properties of mattness, of covering power and/or of improved stability with regard to exudation and post-application anti-migration properties.
  • filler should be understood as meaning colourless or white, solid particles of any form, which are in a form that is insoluble and dispersed in the medium of the composition. These particles, of mineral or organic nature, can give body or rigidity to the composition and/or softness and uniformity to the makeup.
  • the fillers used in the compositions according to the present invention may be of lamellar, globular or spherical form, in the form of fibres or in any form intermediate between these defined forms.
  • the fillers according to the invention may or may not be surface-coated, and in particular they may be surface-treated with silicones, amino acids, fluoro derivatives or any other substance that promotes the dispersion and compatibility of the filler in the composition.
  • fillers that may be used in the compositions according to the invention, mention may be made of talc, mica, kaolin, bentone, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, boron nitride, glass or ceramic microcapsules, composites of silica and titanium dioxide, such as the TSG series sold by Nippon Sheet Glass, polyamide powder (Nylon ® Orgasol from Atochem), poly-3-alanine powder, polyethylene powder, polytetrafluoroethylene (Teflon ® ) powders, lauroyllysine, starch, hollow polymer microspheres, such as EXPANCEL (NOBEL INDUSTRIE), metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate or magnesium myristate, Polypore ® L200 (Chemdal Corporation), silicone resin microbe
  • It may in particular be a hexamethylene diisocyanate/trimethylol hexyllactone polymer.
  • Such particles are especially commercially available, for example, under the name Plastic Powder D-400 ® or Plastic Powder D-800 ® from the company Toshiki, and mixtures thereof.
  • Pulverulent dyestuffs A composition according to the invention may also comprise at least one pulverulent dyestuff.
  • a cosmetic composition in accordance with the invention may advantageously incorporate at least one pulverulent dyestuff chosen from organic or mineral dyestuffs, especially such as the pigments or nacres conventionally used in cosmetic compositions, materials with a specific optical effect, and mixtures thereof.
  • pigments should be understood as meaning white or coloured, mineral or organic particles, which are insoluble in an aqueous solution and which are intended to colour and/or opacify the composition.
  • the pigments may be present in a proportion of from 0.1 % to 40% by weight, especially from 1 % to 30% by weight and in particular from 5% to 15% by weight relative to the total weight of the cosmetic composition.
  • mineral pigments that may be used in the invention, mention may be made of titanium oxide, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide or chromium oxide, ferric blue, manganese violet, ultramarine blue and chromium hydrate.
  • a pigment is sold, for example, under the reference Coverleaf NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30.
  • the dyestuff may also comprise a pigment having a structure that may be, for example, of silica microsphere type containing iron oxide.
  • a pigment having this structure is the product sold by the company Miyoshi under the reference PC Ball PC-LL-100 P, this pigment consisting of silica microspheres containing yellow iron oxide.
  • DPP diketopyrrolopyrroles
  • nacres should be understood as meaning iridescent or non- iridescent coloured particles of any form, especially produced by certain molluscs in their shell, or else synthesized, and which have a colour effect by optical interference.
  • the nacres may be chosen from nacreous pigments such as titanium mica coated with an iron oxide, titanium mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye and also nacreous pigments based on bismuth oxychloride. They may also be mica particles at the surface of which are superposed at least two successive layers of metal oxides and/or of organic dyestuffs.
  • nacres examples include natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride.
  • nacres available on the market mention may be made of the nacres Timica, Flamenco and Duochrome (based on mica) sold by the company Engelhard, the Timiron nacres sold by the company Merck, the Prestige mica-based nacres sold by the company Eckart, and the Sunshine synthetic mica-based nacres sold by the company Sun Chemical.
  • the nacres may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or tint.
  • nacres that may be used in the context of the present invention, mention may especially be made of gold-coloured nacres sold especially by the company Engelhard under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold especially by the company Merck under the names Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold especially by the company Engelhard under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the names Passion orange (Colorona) and Matte orange (17449) (Microna); the brown-coloured nacres sold especially by the company Engelhard under the names Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the bronze n
  • the cosmetic composition according to the invention may also contain at least one material with a specific optical effect.
  • This effect is different to a simple conventional hue effect, i.e. a unified and stabilized effect as produced by standard dyestuffs, for instance monochromatic pigments.
  • the term "stabilized” means lacking an effect of variability of the colour as a function of the angle of observation or alternatively in response to a temperature change.
  • this material may be chosen from particles with a metallic tint, goniochromatic colouring agents, diffracting pigments, thermochromic agents, optical brighteners, and also fibres, especially interference fibres. Needless to say, these various materials may be combined so as to afford the simultaneous manifestation of two effects, or even of a novel effect in accordance with the invention.
  • the particles with a metallic tint that may be used in the invention are chosen in particular from:
  • particles of at least one metal and/or of at least one metal derivative particles comprising a single-material or multi-material organic or mineral substrate, at least partially coated with at least one coat with a metallic tint comprising at least one metal and/or at least one metal derivative, and
  • metals that may be present in said particles, mention may be made, for example, of Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te and Se, and mixtures or alloys thereof.
  • Ag, Au, Cu, Al, Zn, Ni, Mo and Cr and mixtures or alloys thereof are preferred metals.
  • metal derivatives is intended to denote compounds derived from metals, especially oxides, fluorides, chlorides and sulphides.
  • They may also be particles comprising a glass substrate, for instance those sold by the company Nippon Sheet Glass under the name Microglass Metashine.
  • the goniochromatic colouring agent may be chosen, for example, from multilayer interference structures and liquid-crystal colouring agents.
  • symmetrical interference multilayer structures that may be used in the compositions prepared in accordance with the invention are, for example, the following structures: AI/SiOVAI/SiOyAI, pigments having this structure being sold by the company DuPont de Nemours; Cr/MgF2/AI/MgF 2 /Cr, pigments having this structure being sold under the name Chromaflair by the company Flex; MoS2 Si02 AI Si0 2 MoS2; Fe 2 03 Si02 AI/Si02 Fe 2 03, and Fe 2 03 Si02 Fe203 Si02 Fe20 3 , pigments having these structures being sold under the name Sicopearl by the company BASF; MoS 2 /Si0 2 /mica- oxide/Si0 2 /MoS 2 ; Fe 2 03 Si02 mica-oxide/Si02 Fe 2 03; Ti0 2 /Si0 2 /Ti0 2 and ⁇ 2/ ⁇ 2 ⁇ 3/ ⁇ 2; SnO/Ti0 2 /Si0 2 /Ti0
  • these pigments may be the pigments of silica/titanium oxide/tin oxide structure sold under the name Xirona Magic by the company Merck, the pigments of silica/brown iron oxide structure sold under the name Xirona Indian Summer by the company Merck and the pigments of silica/titanium oxide/mica/tin oxide structure sold under the name Xirona Caribbean Blue by the company Merck. Mention may also be made of the Infinite Colors pigments from the company Shiseido. Depending on the thickness and the nature of the various coats, different effects are obtained.
  • the colour changes from green-golden to red-grey for Si0 2 layers of 320 to 350 nm; from red to golden for Si0 2 layers of 380 to 400 nm; from violet to green for Si0 2 layers of 410 to 420 nm; from copper to red for Si0 2 layers of 430 to 440 nm.
  • pigments with a polymeric multilayer structure examples include those sold by the company 3M under the name Color Glitter.
  • liquid-crystal goniochromatic particles examples include those sold by the company Chenix and also the products sold under the name Helicone ® HC by the company Wacker.
  • the cosmetic composition according to the invention may also comprise water-soluble or liposoluble dyes.
  • the liposoluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan brown, DC Yellow 1 1 , DC Violet 2, DC Orange 5 and quinoline yellow.
  • the water-soluble dyes are, for example, beetroot juice and caramel.
  • a cosmetic composition according to the invention may also comprise, in addition, any additive usually used in the field under consideration, for example chosen from additional, volatile or non-volatile oils, gums, gelling agents and/or thickeners, surfactants, film-forming polymers, resins, dispersants, antioxidants, essential oils, preservatives, fragrances, neutralizers, antiseptics, UV-screening agents, cosmetic active agents such as vitamins, moisturizers, emollients or collagen protectors, and mixtures thereof. It is a matter of routine operations for a person skilled in the art to adjust the nature and amount of the additives present in the compositions in accordance with the invention such that the desired cosmetic properties and stability properties of said compositions are not adversely affected thereby.
  • the composition according to the invention comprises pigments and/or fillers chosen from mineral pigments and/or fillers, organic pigments and/or fillers, and mixtures thereof.
  • the composition according to the invention is in a solid or semi-solid form.
  • the composition according to the invention is in a liquid, pasty or gelled form.
  • a composition according to the invention may especially be in the form of a composition for making up and/or caring for the skin or the lips.
  • the cosmetic compositions of the invention may in particular constitute a care product for the face, body, lips, eyelashes or eyebrows, such as a day cream, night cream, makeup- removing cream, anti-sun composition, protective or care body milks, after-sun milks, skincare lotion, gel or mousse, artificial tanning composition, aftershave composition, or antiperspirant.
  • a care product for the face, body, lips, eyelashes or eyebrows such as a day cream, night cream, makeup- removing cream, anti-sun composition, protective or care body milks, after-sun milks, skincare lotion, gel or mousse, artificial tanning composition, aftershave composition, or antiperspirant.
  • the cosmetic compositions of the invention may in particular constitute a makeup product for the face, body, lips, eyelashes or eyebrows. It constitutes in particular a lipstick or lip gloss, a lip balm, a face powder or eyeshadow, a foundation, a tattoo product, a mascara, an eyeliner, a nail varnish, an antiperspirant, or an artificial skin-tanning product.
  • the composition is a mascara.
  • the composition is a foundation.
  • the composition is a lipstick.
  • the composition is a nail varnish.
  • the invention also relates to a method for caring for and/or making up keratin materials, characterized in that at least one composition as defined previously is applied to said keratin materials.
  • oxidized polysaccharides were prepared by oxidation of potato starch sold by the company Roquette (CAS No.: 9005-25-8) using a reactive extrusion process as described in the article "Water soluble oxidized starches by peroxide reactive extrusion” by R.E. Wing and J.L. Willett, Industrial Crops and Products, 7, 1997, pages 45-52. Use was made of a BC21 co-rotating twin-screw extruder sold by the company Clextral and of aqueous hydrogen peroxide solution as oxidizing agent.
  • Compound 1 oxidized potato starch obtained by reactive extrusion in the presence of an 8% aqueous hydrogen peroxide solution at a pH of 8.9.
  • the compound 1 thus obtained has a carbonyl content of 0.77 meq/g and a carboxyl content of 0.239 meq/g and also a CO/COOH ratio of 3.22.
  • Compound 2 oxidized potato starch obtained by reactive extrusion in the presence of an 8% aqueous hydrogen peroxide solution at a pH of 5.7.
  • the compound 2 thus obtained has a carbonyl content of 0.25 meq/g and a carboxyl content of 0.15 meq/g and also a CO/COOH ratio of 1.66.
  • Compound 3 oxidized potato starch obtained by reactive extrusion in the presence of an 8% aqueous hydrogen peroxide solution at a pH of 7.
  • the compound 3 thus obtained has a carbonyl content of 5.09 meq/g and a carboxyl content of 0.396 meq/g and also a CO/COOH ratio of 12.85.
  • Example 2 Formulation with oils
  • Emulsions were prepared with a 70/30 water/oil ratio and 5% by weight of active material, relative to the weight of the final composition, of an oxidized starch as prepared in Example 1 above (compounds 1 to 3 described in Example 1 ).
  • the 7% starch solutions (water + oxidized polysaccharide) were first prepared 24 hours in advance in a 250 ml beaker using a Rayneri mixer with a deflocculating paddle.
  • the emulsions were formulated using a mini Ultra-turrax mixer (Ultra-turrax Tube Drive UTTD), at a maximum stirring speed (9) for 5 minutes.
  • Ultra-turrax mixer Ultra-turrax Tube Drive UTTD
  • the emulsions thus formed were then immediately transferred to a test tube. Microscope observations were made after stirring and macroscopic observations were made over time (after emulsification, then after 1 hour and 3 hours).
  • Jojoba oil e.g.
  • Castor oil (e.g.
  • Parleam oil (e.g., parleam oil
  • oils studied were coloured with 1 drop of ⁇ - carotene.
  • a fine and concentrated emulsion shows, for the oxidized polysaccharides, that the oils tested have excellent emulsification properties.
  • the emulsion is considered to be stable if it remains fine, without release over the edges and without coalescence.
  • control water/oil composition without starch does not form an emulsion and has two separate phases after stirring.
  • compositions with 5% oxidized starch (compounds 1 to 3 described in Example 1 ) and a water/oil ratio of 70/30 form emulsions that are relatively stable; the results are presented in Table 2 below:
  • Castor oil Particularly fine and Stable
  • the compound 3 thus Castor oil Not very concentrated Average stability obtained has a (polar) and polydisperse
  • oxidized polysaccharides according to the invention have good properties for emulsifying hydrocarbon-based, non-volatile oils, in particular polar, hydrocarbon-based, non-volatile oils, the best results being obtained with polar oils that are not very branched and that have at least two unsaturated groups.
  • Example 3 Formulation of a foundation
  • phase A1 The ingredients of phase A1 were introduced into a beaker, the mixture was placed in a Moritz blender then it was brought to 60°C until all the ingredients dissolved.
  • Phase A2 was prepared separately by milling the pigments in a three-roll mill, then this phase was added with stirring to the phase A1.
  • Phase B was heated to 60°C.
  • the emulsion was prepared at 60°C.
  • the two phases must have a temperature in the region of 60°C.
  • Phase B was poured slowly into phase A while gradually increasing the stirring speed of the Moritz blender up to 2500 rpm. After addition, the mixture was stirred for a further 10 minutes at room temperature.
  • the composition was stable and was applied easily to the skin of the face.

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Abstract

La présente invention concerne une composition cosmétique pour maquillage et/ou soins de matériels kératiniques comprenant, dans un milieu de qualité physiologique, au moins : (i) un ou plusieurs polysaccharides oxydés non cationiques de formule (I) et/ou leurs sels organiques ou inorganiques d'acide carboxyliques : P-(CHO)m (COOH)n (I) où : P représente une chaîne de polysaccharides constituée de monosaccharides comportant 5 atomes de carbone ou plus de 5 atomes de carbone, préférentiellement 6 atomes de carbone ou plus et plus particulièrement 6 atomes de carbone, m est tel que la teneur en groupements aldéhyde (CHO) au sein du polysaccharide est comprise dans l'intervalle s'étendant de 0,05 à 6 meq/g, spécialement de 0,07 à 3, plus spécialement de 0,09 à 2 meq/g et encore plus spécialement de 0,1 à 1 meq/g, n est tel que la teneur en groupements carboxyle (COOH) au sein du polysaccharide est comprise dans l'intervalle s'étendant de 0,05 à 0,9 meq/g, spécialement de 0,07 à 0,5 meq/g, plus spécialement de 0,9 à 0,4 meq/g et encore plus spécialement de 0,1 à 0,3 meq/g, et (ii) au moins une huile, préférentiellement une huile polaire.
PCT/EP2011/060142 2010-06-21 2011-06-17 Composition cosmétique comprenant au moins un polysaccharide oxydé non cationique et une huile, préférentiellement une huile non polaire WO2011161020A1 (fr)

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WO2014095426A1 (fr) 2012-12-20 2014-06-26 L'oreal Composition permettant la libération d'un agent bénéfique comprenant un polycondensat de cyclodextrine insoluble dans l'eau et au moins un agent bénéfique
WO2014095427A1 (fr) 2012-12-20 2014-06-26 L'oreal Polycondensat de cyclodextrine insoluble dans l'eau ; utilisations en tant qu'agent de capture
US10085931B2 (en) 2012-03-09 2018-10-02 L'oreal Process for protecting and repairing keratin fibres using anionic oxidized polysaccharides
US10772819B2 (en) 2013-09-12 2020-09-15 L'oreal Process for treating keratin fibres with an oxidised polysaccharide and a sphingosine compound
US10857087B2 (en) 2013-09-12 2020-12-08 L'oreal Process for treating keratin fibres with a polysaccharide and a pyridinedi-carboxylic acid compound
US11045407B2 (en) 2013-09-12 2021-06-29 L'oreal Process for treating keratin fibres with a pyridinedicarboxylic acid compound
WO2022266947A1 (fr) * 2021-06-24 2022-12-29 L'oreal Composition pour le nettoyage et/ou le démaquillage de matières kératiniques
CN115697297A (zh) * 2020-05-13 2023-02-03 佩特尼克医药公司 泌尿生殖器清洁组合物

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10085931B2 (en) 2012-03-09 2018-10-02 L'oreal Process for protecting and repairing keratin fibres using anionic oxidized polysaccharides
WO2014095426A1 (fr) 2012-12-20 2014-06-26 L'oreal Composition permettant la libération d'un agent bénéfique comprenant un polycondensat de cyclodextrine insoluble dans l'eau et au moins un agent bénéfique
WO2014095427A1 (fr) 2012-12-20 2014-06-26 L'oreal Polycondensat de cyclodextrine insoluble dans l'eau ; utilisations en tant qu'agent de capture
US10772819B2 (en) 2013-09-12 2020-09-15 L'oreal Process for treating keratin fibres with an oxidised polysaccharide and a sphingosine compound
US10857087B2 (en) 2013-09-12 2020-12-08 L'oreal Process for treating keratin fibres with a polysaccharide and a pyridinedi-carboxylic acid compound
US11045407B2 (en) 2013-09-12 2021-06-29 L'oreal Process for treating keratin fibres with a pyridinedicarboxylic acid compound
CN115697297A (zh) * 2020-05-13 2023-02-03 佩特尼克医药公司 泌尿生殖器清洁组合物
WO2022266947A1 (fr) * 2021-06-24 2022-12-29 L'oreal Composition pour le nettoyage et/ou le démaquillage de matières kératiniques

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