Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B11/00—Preparation of cellulose ethers
• • 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
  • A61K8/731—Cellulose; Quaternized cellulose derivatives
• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
  • C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
  • C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B3/00—Preparation of cellulose esters of organic acids

Definitions

• Cosmetic composition comprising a modified liposoluble cellulose or cellulose derivative
• the present invention relates to a cosmetic composition for making up or caring for keratin materials such as the skin, including the scalp, both the face and the human body, the lips, the nails, keratin fibers such as the eyelashes, eyebrows, hair comprising a cosmetically acceptable medium containing a liposoluble modified cellulose or a derivative of liposoluble modified cellulose.
• the composition can be a makeup composition such as a loose or compacted powder, a foundation, a blusher or an eyeshadow, a concealer, a blush, a lipstick, a lip balm, a lip gloss. lips, a lip or eye pencil, a mascara, an eyeliner, a nail polish or a product for making up the body or coloring the skin.
• a makeup composition such as a loose or compacted powder, a foundation, a blusher or an eyeshadow, a concealer, a blush, a lipstick, a lip balm, a lip gloss.
• makeup composition is meant a composition intended to deposit a colored film on the skin.
• the makeup compositions preferably comprise a dyed coloring matter than a dye or a pigment.
• Known makeup compositions often exhibit poor resistance over time and in particular poor color fastness. This poor behavior is characterized by a change in color (toning, paling) generally as a result of an interaction with the sebum and / or sweat secreted by the skin in the case of foundation and eyeshadow or an interaction with saliva in the case of lipsticks. This forces the user to remake themselves very often, which can be a waste of time.
• compositions for the lips and the skin are compositions which have the advantage of forming a deposit which does not deposit, at least in part, on the supports with which they are brought into contact (glass , clothes, cigarette, fabrics).
• An improvement in the hold and in the non-transfer, in particular of the lipsticks can be obtained by combining a volatile oil with a film-forming polymer, like silicone resins.
• a volatile oil with a film-forming polymer, like silicone resins.
• these compositions have the disadvantage of leaving on the skin and the lips, after evaporation of the volatile silicone oils, a film which becomes uncomfortable over time (feeling of drying and tightness), eliminating a certain number of women from this type of lipstick.
• the holding properties obtained remain below the expectations of consumers.
• keratin fibers in particular the eyelashes (mascara)
• a person skilled in the art is confronted with problems of resistance to water, to friction, or even to sweat or sebum, which characterized for example by the formation of halos under the eyes and / or the formation of grains due to the crumbling of the mascara film.
• composition which makes it possible to obtain, after application to the eyelashes, a makeup film having good resistance, in particular to water, during bathing or showering for example, to friction, in particular fingers and / or even tears, sweat or sebum.
• the composition of the invention can in particular constitute a product for making up the body, the lips, the nails or keratin fibers such as the eyelashes, of human beings having in particular non-therapeutic care and / or treatment properties. It constitutes in particular a lipstick or a lip gloss, a blush or an eyeshadow, a product for tattooing, a product for making up or caring for keratin fibers, in particular eyelashes (mascara) to be applied in top coat or in base coat, eyeliner, nail polish, artificial skin tanning product, hair coloring or care product.
• a product for making up the body, the lips, the nails or keratin fibers such as the eyelashes
• It constitutes in particular a lipstick or a lip gloss, a blush or an eyeshadow, a product for tattooing, a product for making up or caring for keratin fibers, in particular eyelashes (mascara) to be applied in top coat or in base coat, eyeliner, nail polish, artificial skin tanning product, hair coloring or care product.
• the composition according to the invention is a composition for making up the skin such as a foundation, an eyeshadow, a blush, a concealer product, a body makeup product, a makeup product.
• lips such as a lipstick, a lip gloss, an eyelash makeup product or mascara, a nail makeup product or nail polish
• the subject of the invention is a cosmetic composition, in particular for making up the skin, lips, eyelashes or nails, comprising, in a cosmetically acceptable medium, a liquid fatty phase and a cellulose or a derivative.
• a cosmetically acceptable medium a liquid fatty phase
• a cellulose or a derivative a cellulose or a derivative.
• liposoluble modified cellulose said modified cellulose or said modified cellulose derivative comprising free hydroxyl functions replaced, in whole or in part, by hydrophobic groups chosen from the radicals of formula -OYR, in which:
• - R represents a group chosen from: A) hydrocarbon groups with linear or branched chains, saturated or unsaturated, or cyclic saturated or unsaturated, comprising from 8 to 50 carbon atoms for modified cellulose or from 4 to 50 carbon atoms for the modified cellulose derivative, said groups possibly comprising in their chains one or more aromatic groups and / or one or more heteroatoes chosen from O, N, P, Si, S; said groups possibly being fluorinated or perfluorinated; B) groups of a polymeric nature chosen from polyolefins, hydrogenated or non-hydrogenated polydienes, lipophilic polycondensates and their mixtures,
• - Y represents a single bond or a divalent linking group.
• liposoluble means soluble at a concentration of at least 1% by weight relative to the total weight of the composition, in the majority oil by weight of the liquid fatty phase, at ambient temperature (25 ° C.) and atmospheric pressure. (10 5 Pa).
• hydrocarbon is meant essentially consisting of carbon and hydrogen atoms.
• the invention also relates to a cosmetic process for caring for or making up the skin, the lips, the eyelashes or the nails, consisting in applying to the skin, the lips, the eyelashes or the nails, the composition as defined above. .
• the composition according to the invention is a leave-in composition.
• the invention also relates to the cosmetic use of the composition defined above for improving the hold and / or the non-transfer of makeup on keratin materials.
• such a composition makes it possible to obtain, after application to the eyelashes, a makeup film having good resistance, in particular to water, during bathing or showering for example, rubbing, especially of the fingers and / or even tears, sweat or sebum.
• a subject of the invention is finally the use of a modified liposoluble cellulose or cellulose derivative, said cellulose or said modified cellulose derivative comprising free hydroxyl functions replaced, in whole or in part, by hydrophobic groups chosen from the radicals of formula - OYR, in which:
• - R represents a group chosen from: A) hydrocarbon groups with linear or branched chains, saturated or unsaturated, or cyclic, saturated or unsaturated, comprising from 8 to 50 carbon atoms for modified cellulose or from 4 to 50 carbon atoms for the modified cellulose derivative, said groups possibly comprising in their chains one or more aromatic groups and / or one or more heteroatoms chosen from O, N, P, Si, S; said groups possibly being fluorinated or perfluorinated; B) groups of a polymeric nature chosen from polyolefins, hydrogenated or non-hydrogenated polydienes, lipophilic polycondensates and their mixtures,
• - Y represents a single bond or a divalent bonding group, to obtain a composition of good texture, easy to apply and leading on the skin, the lips or the keratin fibers to a deposit of good behavior and / or which does not transfer.
• R 3 represents an alkyl group comprising from 1 to 10 carbon atoms.
• the liquid fatty phase of the composition according to the invention comprises at least one (that is to say one or more) fatty substances which are liquid at room temperature (25 ° C.) and atmospheric pressure (10 5 Pa), also called oils. , compatible with each other.
• cellulose or “cellulose derivative” is meant, within the meaning of this description, cellulose or cellulose derivative before partial or total substitution of their free hydroxyl functions by hydrophobic groups by hydrophobic groups of formula -OYR for the make it fat soluble.
• modified cellulose or “modified cellulose derivative”, is understood within the meaning of this description the cellulose or the cellulose derivative obtained after partial or total substitution of their free hydroxyl functions by hydrophobic groups by hydrophobic groups of formula - OYR, this modified cellulose or this modified cellulose derivative being liposoluble.
• a cellulose derivative modified by partial or total substitution of its free hydroxyl functions by hydrophobic groups of formula -OYR.
• the cellulose derivative (unmodified) is chosen from cellulose esters or ethers.
• cellulose ester' before modification by the -OY- R groups, is meant, in the foregoing and what follows, a polymer constituted by a sequence in ⁇ (1-4) of esterified anhydroglucose rings partly or totally, the esterification being obtained by reacting all or only part of the free hydroxyl functions of said anhydroglucose rings with a carboxylic acid or a carboxylic acid derivative (acid chloride, acid anhydride,) comprising from 1 to 4 carbon atoms, linear or branched.
• the cellulose ester results from the reaction of part of the free hydroxyl functions of said rings with a carboxylic acid comprising from 1 to 4 carbon atoms.
• the cellulose esters are chosen from acetates, propionates, butyrates, isobutyrates, acetobutyrates, cellulose acetopropionates and their mixtures.
• These cellulose esters can have a weight average molecular weight ranging from 3000 to 1,000,000, preferably from 10,000 to 500,000, preferably from 15,000 to 300,000.
• the invention relates to a cosmetic composition, in particular for making up the skin, the lips, the eyelashes.
• a cosmetic composition in particular for making up the skin, the lips, the eyelashes.
• - R represents a group chosen from: A) hydrocarbon groups with straight or branched chains, saturated or unsaturated, or cyclic, saturated or unsaturated, comprising from 4 to 50 carbon atoms, said groups being able to contain in their chains one or more groups aromatics and / or one or more heteroatoms selected from O, N, P, Si, S; said groups possibly being fluorinated or perfluorinated; B) groups of a polymeric nature chosen from polyolefins, hydrogenated or non-hydrogenated polydienes, lipophilic polycondensates and their mixtures,
• - Y represents a single bond or a divalent linking group.
• cellulose ether is meant, in the above and what follows, a polymer constituted by a chain at (1-4) of partially etherified anhydroglucose rings, part of the free hydroxyl functions of said cycles being substituted by a radical -OR, R being preferably a linear or branched alkyl radical comprising from 1 to 4 carbon atoms.
• the cellulose ethers are therefore preferably chosen from alkyl cellulose ethers having an alkyl group comprising from 1 to 4 carbon atoms such as methyl, propyl, isopropyl, butyl and isobutyl cellulose ethers.
• the liposoluble modified cellulose derivative (final) of the composition according to the invention comprises hydroxyl groups substituted at the same time: a) by groups preferably chosen from carboxylic acid esters comprising from 1 to 4 carbon atoms or the alkyl ethers having an alkyl group comprising from 1 to 4 carbon atoms and b) by “hydrophobic” groups chosen from the radicals of formula -OYR as defined above.
• the modified cellulose and cellulose derivative are liposoluble, that is to say soluble at a concentration of at least 1% by weight relative to the total weight of the composition, in the majority oil by weight of the liquid fatty phase, at temperature ambient (25 ° C) and atmospheric pressure (10 5 Pa).
• the modified cellulose or the modified cellulose derivative are completely soluble in the majority oil by weight of the liquid fatty phase, that is to say completely dissolved at a concentration greater than or equal to 1% by weight, at temperature ambient and atmospheric pressure, in said majority oil.
• the modified cellulose or the modified cellulose derivative are soluble in at least one of between them.
• the advantage of the cellulose or modified cellulose derivative used in the context of the invention lies in the fact that they have good solubility in the liquid fatty phase of the composition according to the invention as defined above and provide the compositions which the include improved resistance properties (resistance to water, saliva or sweat), in particular when the liquid fatty phase mainly comprises a volatile oil.
• These compounds also make it possible to obtain so-called “non-transfer” compositions, in particular when the liquid fatty phase mainly comprises a volatile oil.
• These liposoluble modified cellulose or cellulose derivative according to the present invention are preferably film-forming polymers.
• film-forming polymer is meant a polymer capable of forming on its own or in the presence of an auxiliary film-forming agent, a macroscopically continuous film which adheres to the keratin materials and preferably a cohesive film and better still, a film of which the cohesion and the mechanical properties are such that the said film can be isolable and can be handled in isolation, for example when the said film is produced by casting on a non-stick surface such as a teflon or silicone surface.
• modified cellulose or cellulose derivatives of the composition according to the invention can also play the role of thickener, or even gelling agent of the liquid fatty phase of the composition.
• the cellulose or the cellulose derivative are modified by hydrocarbon (non-polymeric) or polymeric -O-Y-R groups as described below.
• the groups R are non-polymeric hydrocarbon groups corresponding to the definition A) given above, namely they can be a hydrocarbon group, saturated or unsaturated, with a straight or branched chain, cyclic or non-cyclic comprising: - from 4 to 50 atoms when the composition comprises a cellulose derivative, - from 8 to 50 carbon atoms when the composition comprises a modified cellulose, said hydrocarbon group possibly comprising in its chain one or more aromatic groups and / or one or more heteroatoms chosen from O, N, P, Si, S., these groups being able to be fluorinated or perfluorinated. It is specified that these groups are of non-polymeric nature, that is to say that they do not result from the polymerization or polycondensation of several monomers.
• the groups R are chosen from: - straight chain hydrocarbon groups comprising from 8 to 25 carbon atoms for the modified cellulose and straight chain hydrocarbon groups comprising from 4 to 25 carbon atoms for the derivatives modified cellulose, in particular the saturated linear hydrocarbon groups comprising from 8 to 11 carbon atoms and the linear hydrocarbon groups having at least one unsaturation comprising from 8 to 22 carbon atoms. Mention may in particular be made of saturated linear alkyl groups such as n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and their mixtures.
• hydrocarbon groups with branched saturated chains comprising from 8 to 50 carbon atoms for modified cellulose and hydrocarbon groups with branched saturated chains comprising from 4 to 50 carbon atoms for modified cellulose derivatives, preferably from 8 to 50 atoms of carbon. Mention may in particular be made of branched alkyl groups comprising from 8 to 40 carbon atoms.
• cyclohexyl isobornyl, adamantyl, norbornyl groups, - branched and / or cyclic hydrocarbon groups derived from derivatives of unsaturated fatty acids comprising from 12 to 24 carbon atoms, such as the alkyl ketene dimer, - and their associations.
• B / R polymer groups derived from derivatives of unsaturated fatty acids comprising from 12 to 24 carbon atoms, such as the alkyl ketene dimer, - and their associations.
• the groups R can be groups of polymeric nature chosen from polyolefins, polydienes, lipophilic polycondensates such as polyesters, polyamides, polyurethanes, polyureas, copolymers (urea / urethane), polyethers and their blends.
• These groups are chosen from lipophilic hydrophobic groups, preferably liposoluble.
• polyolefins of the polymers obtained by homopolymerization or copolymerization of the monomers chosen from: - olefins, comprising for example from 2 to 20 carbon atoms, in particular copolymers of ⁇ -olefins, the monomers give crystalline homopolymers; and homopolymers or copolymers of branched ⁇ -olefins.
• Mention may in particular be made of the isobutylene homopolymer and the copolymers between ethylene (or propylene) and of ⁇ -olefins with longer chains such as butene, hexene, octene, decene, dodecene.
• the polydienes can be chosen from the polydienes resulting from the polymerization of dienes comprising for example from 4 to 20 carbon atoms, such as butadiene, isoprene, hexadiene, or from polymers resulting from the polymerization of dienes comprising for example from 4 to 20 carbon atoms with other vinyl monomers such as the ⁇ -olefins mentioned above and / or with styrene or substituted styrenes.
• Examples of polydienes are polybutadienes, polyisoprene, preferably hydrogenated.
• the lipophilic polycondensates can be chosen from polyesters, polyamides, polyesteramides, polyurethanes, polycarbonates, polyureas, copolymers (urea / urethane), polyethers, provided that they are lipophilic
• lipophilic polyesters mention may be made of those resulting from the polyesterification of at least one polyol such as a diol or a triol with at least one polycarboxylic acid, such as a diacid or a triacidic carboxylic acid or a diacid or triacid carboxylic derivative (such as an acid chloride, an acid anhydride), or an alkyl diester comprising from 1 to 5 carbon atoms.
• the polyester is lipophilic insofar as at least the diol, the polyol, the dicarboxylic acid or the triacid carboxylic is lipophilic.
• polyol can in particular be chosen from:
• Dimer diols are branched diols, generally C 36 , often in mixtures, aliphatic and / or alicyclic, prepared from “dimer fatty acids” which are compounds of the same structure but having two carboxylic acid ends ( instead of diol ends).
• dimer fatty acids are compounds of the same structure but having two carboxylic acid ends ( instead of diol ends).
• the transformation of dimer fatty acids into dimer diols can be done: - either by hydrogenation of methyl esters of dimer fatty acids, - either by direct dimerization of oleic alcohol.
• dimeric fatty acids reference may be made to US Patents 3,157,681 and 5,998,570.
• hydroxyl end polymers are defined for example in patent FR 2,782,723. They are preferably chosen from the group comprising homo and copolymers of butadiene, isoprene and 1, 3-pentadiene. They are oligomers of M w ⁇ 7000, preferably between 1000 and 5000 having a hydroxyl functionality (at the ends) between 1, 8 and 3, and preferably close to 2. These polymers are preferably used hydrogenated.
• ATOFINA under the brands POLY BD R-45HT and POLY BD R-20LM, which will preferably be used hydrogenated.
• Polyolefins, homopolymers or copolymers with ⁇ , ⁇ hydroxylated ends can also be used, such as:
• oils carrying from 2 to 3 hydroxyl groups the preferred oils are, of course, oils carrying two hydroxyl groups per chain, such as the monoglycerides of structure:
• R 9 being a linear or branched, saturated or unsaturated aliphatic chain having from 6 to 50 carbon atoms.
• Such glycerol monoesters correspond to the general formula:
• polycarboxylic acid such as ethylene glycol, propylene glycol, diethylene glycol, neopentylglycol, 1,4-butane diol, furan dimethanol, cyclohexane dimethanol , glycerol, trimethylol propane, pentaerythritol and mixtures thereof.
• linear branched or cyclic dicarboxylic acids preferably comprising from 4 to 60 carbon atoms, or their derivatives: anydrides, acid dichloride, diesters resulting from the reaction with a C1-C6 alcohol and in particular those which comprise: - a linear or branched C 3 -C 50 alkyl or alkenyl chain, which may comprise one or more unsaturations, conjugated or not, which may comprise saturated or unsaturated rings, and be interrupted by one or more heteroatoms of the type -O-, -S-, -N-; - A C 8 -C 3 cycloalkyl chain (including the two atoms of the acid groups or acid derivatives), optionally substituted by one or more CC 10 alkyl groups;
• a is an integer from 2 to 20; such as, for example, adipic, glutaric, succinic, pimelic, azelaic, sebacic, suberic acids, and their derivatives. Mention may also be made, as aliphatic diacid, of itaconic acid and maleic acid.
• dimer fatty acids which are branched diacids, generally C 36 , often in mixtures, aliphatic and / or alicyclic. These dimeric fatty acids are defined in particular in US Pat. No. 3,157,681.
• aromatic diacids and derivatives there may be mentioned:
• the benzene ring possibly being optionally substituted, in particular by one or more alkyl groups, preferably in C ⁇ -C 6 :
• dichloride and diesters derivatives in particular the CC 6 alkyl diesters such as methyl and ethyl, of these acids;
• polyesters As lipophilic polyesters, mention may also be made of branched polyesters with a long C10-40 alkyl chain and carrying at least two reactive groups such as poly (12-hydroxystearate) with hydroxyl ends.
• polyesteramides of those obtained by reaction of amino alcohols such as ethanolamine with the diacids and polyacids mentioned in 3.1 / b).
• polyamides of those obtained by condensation between an aliphatic, cycloaliphatic or aromatic dicarboxylic acid (or ester derivative of CC 4 ) comprising from 3 to 50 carbon atoms and a diamine comprising from 2 to 50 carbon atoms.
• the diacids being able to be chosen among the diacids mentioned above with in addition the dimeric fatty acids (resulting from the condensation between two molecules of mono unsaturated fatty acids), the diamines being able to be chosen among ethylenediamine, 1, 2-diaminopropane, 1, 3-diaminopropane, 1, 4-diaminobutane, 1, 2-diamino-2-methylpropane, 1, 6-diaminohexane, 1 J0-diaminodecane, isophoronediamine, adamantanediamine, 2,6-diaminopyridine.
• dimer diamines can be used, with the same structure as the dimer diols mentioned above, but having two primary amine functions in place of the two hydroxyls. They can be obtained from dimeric fatty acids, such as dimer-diols as indicated in the article by R. HOFFER cited above. Finally, it is also possible to use diamines of structure H 2 N- D-NH 2 , where D is an alkyl chain, linear or branched containing from 8 to 40 carbon atoms.
• diamines As an example of such diamines, mention may be made of: - 1, 10-diamino decane and 1, 12-diamino dodecane,
• DUOMEEN C or CD cocopropylene diamine (distilled or not)
• DUOMEEN HT Tallowpropylene diamine hydrogenated
• DUOMEEN M C 16 . 22 alkylpropylene diamine
• DUOMEEN O oleylpropylene diamine
• DUOMEEN T Tallow propylene diamine
• polyurethanes polyureas and polyureas-urethanes
• aliphatic, cycloaliphatic and / or aromatic diisocyanates comprising from 4 to 100 carbon atoms, preferably from 4 to 30 carbon atoms such as hexamethylene diisocyanate, isophorone diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate and diols as defined above, or diamine
• the group R as defined above can carry one or more groups capable of establishing a hydrogen bond.
• group capable of establishing a hydrogen bond is meant a group comprising either a hydrogen atom linked to an electronegative atom or an electronegative atom.
• the group comprises a hydrogen atom linked to an electronegative atom
• the hydrogen atom can interact with another electronegative atom carried, for example by another molecule, such as keratin, to form a hydrogen bond.
• the grouping includes an electronegative atom
• the electronegative atom can interact with an atom of hydrogen linked to an electronegative atom carried, for example by another molecule, such as keratin, to form a hydrogen bond.
• these groups capable of establishing a hydrogen bond can be groups chosen from the following groups: - hydroxyl -OH; - carboxylic acid -COOH; - amino -NR ⁇ with Ri and R 2 , identical or different; - pyridino of formula:
• Derivatives carrying at least one group capable of establishing a hydrogen bond are particularly advantageous, because they provide compositions containing them with very high adhesion properties thanks to the ability of these groups to establish a hydrogen bond with keratin materials .
• the modified liposoluble cellulose or cellulose derivative in accordance with the invention may represent from 0.5 to 50%, preferably from 1 to 45%, better still from 4 to 40% and even better still from 5 to 30% by weight of material. dry (or active material) relative to the total weight of the composition according to the invention.
• the fat-soluble derivative is present in a content of at least 4% by weight, preferably at least 5% by weight relative to the total weight of the composition.
• the composition comprises a modified cellulose derivative
• the latter may be prepared by various methods within the reach of the skilled person and, in particular according to the following two main synthetic routes: - either starting from ester or ether derivatives of celluloses and reactants are reacted on these derivatives with reagents suitable for grafting onto the free hydroxyl functions, groups of formula -YR as defined above (named after this description Route A); - Either one starts from celluloses already modified with -YR groups as defined above and reacts on these celluloses thus modified with suitable reagents to obtain the esterification or etherification of at least part of the free hydroxyl functions. (named route B).
• the preferred route for the synthesis of the cellulose derivatives of the invention is route A. Only this route will be the subject of a detailed description in the present application.
• composition comprises a modified cellulose
• this may be prepared by the same synthetic route A above used for the modified cellulose derivative:
• the starting reagent is a cellulose, a cellulose ester or a cellulose ether comprising a certain number of free OH functions to which appropriate reagents will react to give -O-Y-R groups.
• divalent linking groups -Y- are -C- groups, -O-Y- being a
• polymers of the invention by partially or totally transesterifying the ester groups of the initial cellulose ester with a fatty acid HOOC-R or with a methyl ester of this fatty acid of formula CH3OC ( O) -R, -R having the above definition and R being in particular a hydrocarbon group with a straight or branched or cyclic chain.
• This transesterification can also be done by a mixture of HOOC-R fatty acids, or methyl esters of CH3-O-C (O) -R fatty acids, the radicals R being different.
• the starting reagent is a cellulose ester
• partial or total transesterification is carried out of the ester groups already present in the initial cellulose ester.
• This reaction can be carried out using a fatty acid R-CCOH (R corresponding to the definition given above) or a mixture of fatty acids with R radicals of different natures.
• This reaction can, according to an advantageous embodiment, be carried out not starting from a fatty acid, but from its methyl ester CH3-OC (O) -R, or by a mixture of methyl esters of fatty acids, by catalyzing the reaction with sodium methylate and distilling the methyl alcohol formed during the reaction.
• - carboxylic acids n-hexanoic, n-heptanoic, n-octanoic, n-nonanoic, n-decanoic, n-undecanoic, in the case where the group R is a linear alkyl radical,
• this route is not applicable if one starts either from a cellulose ester but from a cellulose or a cellulose ether as defined.
• the rate of substitution of the OH functions is limited. If a high substitution rate is desired, it is preferable to directly esterify the residual OH of the starting cellulose ester using a chloride or anhydrous fatty acid.
• suitable epoxy reagents can be 1,2-epoxyoctane,
• R 5 representing a chain included in the constitution of the chain R, said chain R being represented here by the group -CH 2 -R 5 .
• this reaction can take place in two stages, with the first stage being a preliminary reaction of the aldehyde with a diol, such as glycol, to form a cyclic acetal:
• R 6 representing a chain forming part of the chain R, said chain R being represented here by the group -CH- (CH 2 -CH 2 -OH) -R 6 .
• R 7 representing a chain entering into the constitution of the chain R, represented here by the group -CH 2 -CH 2 -R 7 and R a and R f representing a chain entering into the constitution of the chain R, represented here by the group -CHR a -
• esterification reactions include the following reactions, reactions for which Y represents a CO bonding group: reaction with a carboxylic acid R-CO 2 H:
• R 8 , R 9 and R 10 being such that - (CHR 8 ) -CR 9 R 10 -CO 2 H represents R.
• Esterification is preferred by reaction with an acid chloride or acid anhydride rather than by reaction with a carboxylic acid.
• Suitable esterification reagents can be: octanoic acid, ethyl-2-hexanoic acid, nonanoic acid, decanoic acid, neodecanoic acid, undecanoic acid, dodecanoic acid, isononanoic acid, isodecanoic acid, isododecanoic acid, isostearic acid.
• neodecanoyl neodecanoyl, undecanoyl, decanoyl, dodecanoyl, and isononanoyl chlorides.
• alkyl succinyl anhydrides and in particular: isooctadecenyl succinic anhydride, 1-octenyl succinic anhydride, 1-nonenyl succinic anhydride.
• esterification can also be carried out by reaction of the residual -OH groups of the cellulose derivative with the reactive Alkyl Ketene Dimer (AKD) with monofunctional ketene cyclic group.
• alkyl succinyl anhydrides and in particular: isooctadecenyl succinic anhydride, 1-octenyl succinic anhydride, 1-nonenyl succinic anhydride.
• esterification can also be carried out by reaction of the residual -OH groups of the cellulose derivative with the reactive Alkyl Ketene Dimer (AKD) with monofunctional ketene cyclic group.
• ALD reactive Alkyl Ketene Dimer
• AKDs are obtained by reaction from a mixture of unsaturated fatty acids comprising from 14 to 22 carbon atoms, and have the following formula:
• R 14 and R 15 identical or different are a C 8 alkyl chain. 20 , such that the sum of the number of carbon atoms in the chains R 14 and R 15 ranges from 30 to 36 atoms.
• R 14 C 14 H 2.
• R 5 C 16 H 33 .
• Suitable isocyanate reagents may be butyl, isobutyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, isocyanate phenyl. This reaction is particularly preferred.
• R 12 which may be a linear, branched or cyclic hydrocarbon chain, from 1 to 500 carbon atoms , saturated or unsaturated, which may contain one or more atoms of O, N, S, Si and / or P, preferably from 1 to 10 carbon atoms, the R 12 therefore having the same definition as the R 3 defined above.
• the reactive functions Xi with respect to the free hydroxyl functions of the initial cellulose derivative can be chosen from the epoxide, aldehyde, acetal, halogen (chlorine, bromine) functions. , iodine), ethylenic, carboxylic acid or derivative (chloride, anhydride, CC 4 alkyl ester), carbonate, sulfonic acid or sulfonyl chloride, isocyanate, monoalkoxysilane.
• the starting POL-Xi polymers need to be synthesized, apart from those for which X 1 is a vinyl type reactive double bond, many of which are commercially available.
• the POL-Xi polymers can be synthesized for example from a polymer comprising a reactive function different from X ⁇ which is transformed by conventional reactions into an appropriate Xi.
• a polyester generally comprises, at the end of preparation, a reactive -CO 2 H end and a -OH end. It should be noted that this -OH end will preferably be blocked by an inert group devoid of labile hydrogen, so as not to interfere with the grafting reaction on the cellulose or the starting cellulose derivative (cellulose ester or ether) .
• a polyamide which has a reactive -CO 2 H end and an -NH 2 end to be protected by a group which is inert with respect to the grafting reaction with the starting cellulose derivative. It is also possible to introduce a reactive group X ⁇ at the polycondensate, by introducing into the reaction medium, during polycondensation, a reagent carrying the group X- ⁇ , which must be inert with respect to the type of polycondensation chosen or inert under the experimental conditions of polycondensation, and of a single group capable of participating in the polycondensation. This reagent is therefore monofunctional with respect to polycondensation and therefore serves as a chain limiter.
• This monofunctional reagent with respect to polycondensation and carrying a group which is reactive with respect to the hydroxyl functions of the starting cellulose derivative, is preferably introduced during the polycondensation, so that the chains of the polymer are only terminated by a single reactive group X ⁇
• the grafting reaction may consist, firstly, of transforming all or part of the hydroxyl functions of the cellulose or of the starting cellulose derivative (cellulose ester or ether) into reactive functions, then, in a second time, reacting said reactive functions with the appropriate reactive ends of polymers comprising said hydrocarbon chain R.
• the following reaction may be cited:
• the polymer grafts can be: - polyolefins (homo- or copolymers), preferably, semi-crystalline; - polydienes, preferably hydrogenated; - lipophilic polycondensates such as: polyesters, polyamides, polyurethanes, polyureas, copolymers (urea / urethane), polyethers, all lipophilic;
• the liquid fatty phase of the composition according to the invention comprises at least liquid fatty substance at room temperature (25 ° C) and atmospheric pressure (10 5 Pa), also called oil.
• the liquid fatty phase of the composition may be a continuous fatty phase.
• the oils can be volatile or non-volatile, polar or nonpolar.
• composition according to the invention advantageously comprises at least one volatile oil.
• volatile oil is meant within the meaning of the invention any non-aqueous medium capable of evaporating on contact with keratin materials in less than an hour, at room temperature and atmospheric pressure.
• the volatile oil (s) of the invention are volatile cosmetic oils, liquid at room temperature, having a non-zero vapor pressure, at room temperature and atmospheric pressure, ranging from 0.13 Pa to 40,000 Pa (10 "3 to 300 mm Hg), in particular ranging from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mm Hg) ).
• non-volatile oil an oil which remains on keratin materials at room temperature and atmospheric pressure for at least several hours and in particular having a vapor pressure of less than 0J3 Pa (0.01 mm Hg).
• oils can be hydrocarbon oils, silicone oils, or mixtures thereof.
• hydrocarbon-based oil means an oil mainly containing hydrogen and carbon atoms and optionally oxygen atoms, nitrogen, sulfur, phosphorus.
• Volatile hydrocarbon oils may be chosen from hydrocarbon oils having 8 to 16 carbon atoms, and especially branched alkanes, C 8 -C 16 isoalkanes C 8 -C 16 petroleum origin (also known as isoparaffins), isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, and for example the oils sold under the trade names of Isopars' or Permyls.
• volatile silicones can also be used, such as, for example, volatile linear or cyclic silicone oils, in particular those having a viscosity ⁇ 5 centistokes (5 10 "6 m 2 / s), and in particular having from 2 to 10 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms
• volatile silicone oil which can be used in the invention, there may be mentioned in particular octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane and their mixtures.
• the volatile oil can be present in the composition according to the invention in a content ranging from 0.1% to 95% by weight, relative to the weight of the composition, preferably from 1 to 65% by weight and better still from 2 at 50% by weight.
• composition can also comprise at least one non-volatile oil, and in particular chosen from non-volatile hydrocarbon and / or silicone oils.
• non-volatile hydrocarbon-based oil there may be mentioned in particular:
• oils of vegetable origin such as triglycerides consisting of fatty acid and glycerol esters, the fatty acids of which may have varying chain lengths from C 4 to C 24 , which can be linear or branched, saturated or unsaturated; these oils are in particular the oils of wheat germ, sunflower, grapeseed, sesame, corn, apricot, castor, shea, avocado, olive, soybean, almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower,nadooulier, passionflower, muscat rose; or the triglycerides of caprylic / capric acids such as those sold by the company Stéarineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit
• oils of formula R - linear or branched hydrocarbons, of mineral or synthetic origin such as petrolatum, polydecenes, hydrogenated polyisobutene such as parlam, squalane, paraffin oils and their mixtures; - synthetic esters such as oils of formula R.
• Ri represents the remainder of a linear or branched fatty acid containing from 1 to 40 carbon atoms and R 2 represents a hydrocarbon chain in particular branched containing from 1 to 40 carbon atoms provided that R 5 + R ⁇ is> 10, such as, for example, Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C- ⁇ alcohol benzoate 2 to C 15 , hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, isostearate isostearate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxyl esters such as isostearyl lactate, di-isostearyl malate; and pentaerythritol esters;
• Purcellin oil
• fatty alcohols which are liquid at room temperature with a branched and / or unsaturated carbon chain having from 12 to 26 carbon atoms such as octyl dodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, 2- undecylpentadecanol; - higher fatty acids such as oleic acid, linoleic acid, linolenic acid; and their mixtures.
• the non-volatile silicone oils which can be used in the composition according to the invention can be the non-volatile polydimethylsiloxanes (PDMS), the polydimethylsiloxanes comprising alkyl or alkoxy groups, during and / or at the end of the silicone chain, groups each having from 2 to 24 carbon atoms, phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates and their mixtures.
• PDMS non-volatile polydimethylsiloxanes
• phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, dipheny
• the non-volatile oils may be present in the composition according to the invention in a content ranging from 0.01 to 95% by weight, preferably from 0% to 80% by weight, relative to the total weight of the composition, and better still from 1% to 50% by weight (especially 0J% to 10%).
• the liquid fatty phase can represent from 0.01 to 98% by weight relative to the total weight of the composition, preferably from 0.05 to 75% and better still from 1 to 60% by weight.
• composition according to the invention may comprise an aqueous phase consisting essentially of water or of a mixture of water and of water-miscible solvent (miscibility in water greater than 50% by weight at 25 ° C) as lower monoalcohols having from 1 to 5 carbon atoms such as ethanol, isopropanol, glycols having from 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1, 3-butylene glycol, dipropylene glycol, C3-C4 ketones, C2-C4 aldehydes and mixtures thereof.
• aqueous phase consisting essentially of water or of a mixture of water and of water-miscible solvent (miscibility in water greater than 50% by weight at 25 ° C) as lower monoalcohols having from 1 to 5 carbon atoms such as ethanol, isopropanol, glycols having from 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1, 3-butylene glycol, dipropy
• the aqueous phase (water and optionally the water-miscible solvent) may be present in a content ranging from 0% to 65% by weight, relative to the total weight of the composition, preferably ranging from 1% to 55% by weight. weight and better from 5 to 50% by weight.
• the water and / or the water-soluble solvent (s) can be introduced as such into the formulation according to the invention or be incorporated therein, by means of one or more ingredients constituting said composition.
• water can in particular be introduced into the composition by means of the introduction of latex or pseudolatex, that is to say of aqueous dispersion of polymer particles.
• the composition according to the invention is anhydrous.
• anhydrous composition is meant a composition comprising an aqueous phase as defined above in a proportion less than or equal to 10%, preferably less than or equal to 5% and better still, less than or equal to 3%, or even free of water.
• composition according to the invention comprises a cosmetically acceptable medium, that is to say compatible with keratin materials (tolerance, toxicology and acceptable feel).
• composition according to the invention may also comprise at least one fatty substance that is solid at room temperature, in particular chosen from waxes, pasty fatty substances, gums and their mixtures. These fatty substances can be of animal, vegetable, mineral or synthetic origin.
• composition according to the invention can comprise a wax or a mixture of waxes.
• the wax considered in the context of the present invention is generally a lipophilic compound, solid at room temperature (25 ° C), with reversible solid / liquid state change, having a melting point greater than or equal to 30 ° C up to 200 ° C.
• the waxes suitable for the invention can have a melting point greater than approximately 30 ° C., preferably greater than 45 ° C. and in particular greater than 55 ° C.
• the melting point of the wax can be measured using a differential scanning calorimeter (D.S.C.), for example the calorimeter sold under the name DSC
• the measurement protocol is as follows:
• a 15 mg sample of product placed in a crucible is subjected to a first temperature rise ranging from 0 ° C to 120 ° C, at the heating rate of 10 ° C / minute, then is cooled from 120 ° C to 0 ° C at a cooling rate of 10 ° C / minute and finally subjected to a second temperature rise ranging from 0 ° C to 120 ° C at a heating rate of 5 ° C / minute.
• the variation in the difference in power absorbed by the empty crucible and by the crucible containing the product sample is measured as a function of the temperature.
• the melting point of the compound is the value of the temperature corresponding to the top of the peak of the curve representing the variation of the difference in absorbed power as a function of the temperature.
• the waxes capable of being used in the compositions according to the invention are chosen from waxes, solid and rigid at room temperature, of animal, vegetable, mineral or synthetic origin and their mixtures.
• the wax can also have a hardness ranging from 0.05 MPa to 30 MPa, and preferably ranging from 6 MPa to 15 MPa.
• the hardness is determined by measuring the compressive force measured at 20 ° C using the texturometer sold under the name TA-TX2i by the company RHEO, equipped with a stainless steel cylinder with a diameter of 2 mm. moving at the measuring speed of 0J mm / s, and penetrating into the wax at a penetration depth of 0.3 mm.
• the measurement protocol is as follows: The wax is melted at a temperature equal to the melting point of the wax + 20 ° C. The melted wax is poured into a container 30 mm in diameter and 20 mm deep. The wax is recrystallized at room temperature (25 ° C) for 24 hours, then the wax is stored for at least 1 hour at 20 ° C before performing the hardness measurement.
• the hardness value is the maximum compression force measured divided by the surface area of the texturometer cylinder in contact with the wax.
• hydrocarbon waxes such as beeswax, lanolin wax; rice wax, Japanese wax, Camauba wax, Candellila wax, microcrystalline waxes, paraffins and ozokerite; the waxes of polyethylene, the waxes obtained by the Fisher-Tropsch synthesis and the waxy copolymers as well as their esters.
• waxes obtained by catalytic hydrogenation of animal or vegetable oils having fatty chains, linear or branched, of C8-C32 Mention may also be made of the waxes obtained by catalytic hydrogenation of animal or vegetable oils having fatty chains, linear or branched, of C8-C32.
• hydrogenated jojoba oil isomerized jojoba oil such as trans isomerized partially hydrogenated jojoba oil manufactured or sold by the company Désert Whale under the commercial reference ISO-JOJOBA-50 ® , hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil and hydrogenated lanolin oil, di- (trimethylol-1, 1, 1 propane) tetrastearate sold under the name “ HEST 2T-4S ”by the company HETERENE, di- (trimethylol-1, 1, 1 propane) tetrabehenate sold under the name HEST 2T-4B by the company HETERENE.
• silicone waxes such as alkyl or alkoxy-dimethicone having from 16 to 45 carbon atoms, fluorinated waxes.
• Such waxes are described in application FR-A-2792190.
• compositions according to the invention can comprise at least one so-called sticky wax, that is to say having a stickiness greater than or equal to 0.7 N.s and a hardness less than or equal to 3.5
• the stickiness of the wax is determined by measuring the change in force (compression force or stretching force) as a function of time, at 20 ° C using the texturometer sold under the name "TA-TX2T ® ”by RHEO, equipped with a cone-shaped acrylic polymer mobile forming an angle of
• the measurement protocol is as follows: The wax is melted at a temperature equal to the melting point of the wax + 10 ° C. The melted wax is poured into a container 25 mm in diameter and 20 mm deep. The wax is recrystallized at room temperature (25 ° C) for 24 hours so that the surface of the wax is flat and smooth, then the wax is stored for at least 1 hour at 20 ° C before measuring the tights.
• the mobile of the texturometer is moved at the speed of 0.5 mm / s, then enters the wax to a penetration depth of 2 mm.
• the mobile is held fixed for 1 second (corresponding to the relaxation time) then is removed at the speed of 0.5 mm / s.
• the force decreases sharply until it becomes zero, then, when the mobile is removed, the force (stretching force) becomes negative and then increases again towards the value 0.
• the tights corresponds to the integral of the force curve as a function of time for the part of the curve corresponding to the negative values of the force (stretching force).
• the value of the adhesive is expressed in Ns. The hardness is measured according to the protocol described above.
• a sticky wax it is possible to use a C 20 -C 0 alkyl (hydroxystearyloxy) stearate (the alkyl group comprising from 20 to 40 carbon atoms), such as for example the waxes sold under the names “Kester Wax K 82 P ® "and” Kester Wax K 80 P ® "by the company KOSTER KEUNEN. Mention may also be made of the microcrystalline wax sold under the reference SP18 by the company STRAHL and PITSCH which has a hardness of approximately 0.46 MPa and a tack value of approximately 1 Ns
• the waxes mentioned above generally have a starting melting point below 45 ° C.
• the wax (es) can be present in the form of an aqueous microdispersion of wax.
• aqueous wax microdispersion is understood to mean an aqueous dispersion of wax particles, in which the size of said wax particles is less than or equal to approximately 1 ⁇ m.
• Wax microdispersions are stable dispersions of colloidal wax particles, and are described in particular in "Microemulsions Theory and Practice", LM Prince Ed., Académie Press (1977) pages 21-32. In particular, these wax microdispersions can be obtained by melting the wax in the presence of a surfactant, and optionally part of the water, then progressive addition of hot water with stirring.
• the wax microdispersion can also be obtained by stirring the mixture of wax, surfactant and water using stirring means such as ultrasound, high pressure homogenizer, turbines.
• the particles of the wax microdispersion preferably have mean dimensions of less than 1 ⁇ m (in particular ranging from 0.02 ⁇ m to 0.99 ⁇ m), preferably less than 0.5 ⁇ m (in particular ranging from 0.06 ⁇ m to 0 , 5 ⁇ m).
• These particles consist essentially of a wax or a mixture of waxes. They may, however, in a minor proportion comprise oily and / or pasty fatty additives, a surfactant and / or a usual fat-soluble additive / active.
• pasty fatty substance means a lipophilic fatty compound comprising at the temperature of 23 ° C. a liquid fraction and a solid fraction.
• Said pasty compound preferably has a hardness at 20 ° C ranging from 0.001 to 0.5 MPa, preferably from 0.002 to 0.4 MPa.
• the hardness is measured according to a method of penetration of a probe into a sample of compound and in particular using a texture analyzer (for example TA-XT2Î from Rhéo) equipped with a stainless steel cylinder of 2 mm in diameter.
• the hardness measurement is carried out at 20 ° C in the center of 5 samples.
• the cylinder is introduced into each sample at a pre-speed of 1 mm / s and then at a measurement speed of 0J mm / s, the penetration depth being 0.3 mm.
• the value recorded for the hardness is that of the maximum peak.
• the liquid fraction of the pasty compound measured at 23 ° C preferably represents 9 to 97% by weight of the compound.
• This liquid fraction at 23 ° C represents preferably between 15 and 85%, more preferably between 40 and 85% by weight.
• the liquid fraction by weight of the pasty compound at 23 ° C is equal to the ratio of the enthalpy of fusion consumed at 23 ° C to the enthalpy of fusion of the pasty compound.
• the enthalpy of fusion of the pasty compound is the enthalpy consumed by the compound to pass from the solid state to the liquid state.
• the pasty compound is said to be in the solid state when all of its mass is in crystalline solid form.
• the pasty compound is said to be in the liquid state when all of its mass is in liquid form.
• the enthalpy of fusion of the pasty compound is equal to the area under the curve of the thermogram obtained using a differential scanning calorimeter (DS C), such as the calorimeter sold under the name MDSC 2920 by the company TA instrument, with a temperature rise of 5 or 10 ° C per minute, according to ISO 11357-3: 1999.
• DS C differential scanning calorimeter
• the enthalpy of fusion of the pasty compound is the amount of energy required to bring the compound from the solid state to the liquid state. It is expressed in J / g.
• the enthalpy of fusion consumed at 23 ° C is the amount of energy absorbed by the sample to go from the solid state to the state it presents at 23 ° C consisting of a liquid fraction and a solid fraction.
• the liquid fraction of the pasty compound measured at 32 ° C. preferably represents from 30 to 100% by weight of the compound, preferably from 80 to 100%, more preferably from 90 to 100% by weight of the compound.
• the temperature at the end of the melting range of the pasty compound is less than or equal to 32 ° C.
• the liquid fraction of the pasty compound measured at 32 ° C is equal to the ratio of the enthalpy of fusion consumed at 32 ° C to the enthalpy of fusion of the pasty compound.
• the enthalpy of fusion consumed at 32 ° C is calculated in the same way as the enthalpy of fusion consumed at 23 ° C.
• the pasty bodies are generally hydrocarbon compounds such as lanolins and their derivatives or even PDMSs.
• the nature and quantity of the solid bodies are a function of the mechanical properties and of the desired textures.
• the composition may contain from 0.1 to 50% by weight of waxes, relative to the total weight of the composition, better from 1 to 40% and even better still from 5 to 20% by weight.
• composition according to the invention may also comprise, in addition to the modified cellulose or the modified cellulose derivative, a so-called additional film-forming polymer.
• film-forming polymer mention may in particular be made of acrylic polymers, polyurethanes, polyesters, polyamides, polyureas, cellulosic polymers other than liposoluble modified cellulose derivatives.
• the additional film-forming polymers may be soluble or dispersible in a liquid fatty phase, which may be the liquid fatty phase of the composition, they may also be chosen from film-forming polymers which are water-soluble or dispersible in an aqueous phase (also called latex).
• the additional film-forming polymer may be present in a content ranging from 0J to 30% by weight in dry matter, relative to the total weight of the composition and better still from 0.5 to 15% by weight.
• the composition according to the invention may also comprise one or more coloring materials chosen from water-soluble dyes, and pulverulent coloring materials such as pigments, nacres and flakes well known to those skilled in the art.
• the coloring matters may be present, in the composition, in a content ranging from 0.01% to 50% by weight, relative to the weight of the composition, preferably from 0.01% to 30% by weight and better still from 1 at 25% by weight.
• pigments should be understood to mean particles of any shape, white or colored, mineral or organic, insoluble in the physiological medium, intended to color the composition. By nacres, it is necessary to understand particles of any iridescent shape, in particular produced by certain molluscs in their shell or else synthesized.
• the pigments can be white or colored, mineral and / or organic.
• mineral pigments mention may be made of titanium dioxide, optionally surface-treated, zirconium or cerium oxides, as well as oxides of zinc, iron (black, yellow or red) or chromium, violet of manganese, ultramarine blue, chromium hydrate and ferric blue, metallic powders such as aluminum powder, copper powder.
• organic pigments mention may be made of carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium, aluminum.
• effect pigments such as particles comprising an organic or mineral, natural or synthetic substrate, for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas, said substrate being whether or not covered with metallic substances such as aluminum, gold, silver, platinum, copper, bronze, or metallic oxides such as titanium dioxide, iron oxide, chromium oxide and their mixtures.
• the pearlescent pigments can be chosen from white pearlescent pigments such as mica coated with titanium or bismuth oxychloride, colored pearlescent pigments such as titanium mica coated with iron oxides, mica titanium coated with in particular blue ferric or chromium oxide, titanium mica coated with an organic pigment of the aforementioned type as well as pearlescent pigments based on bismuth oxychloride. . It is also possible to use interference pigments, in particular liquid crystal or multilayer pigments.
• the liposoluble dyes are for example Sudan red, D&C Red 17, D&C Green 6, ⁇ -carotene, soybean oil, Sudan brown, D&C Yellow 11 Je D&C Violet 2, D&C orange 5, quinoline yellow, annatto.
• the water-soluble dyes are for example beet juice, methylene blue, disodium salt of culvert, disodium salt of alizarin green, quinoline yellow, the trisodium salt of amaranth, the disodium salt of tartrazine, the monosodium salt of rhodamine, the disodium salt of fuchsin, xanthophyll.
• the composition according to the invention may comprise at least one filler, in particular in a content ranging from 0.01% to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.01% to 30% by weight. weight.
• fillers it is necessary to understand particles of any shape, colorless or white, mineral or synthetic, insoluble in the medium of the composition regardless of the temperature at which the composition is produced. These charges are used in particular to modify the rheology or the texture of the composition.
• the fillers can be mineral or organic of any shape, platelet, spherical or oblong, whatever the crystallographic form (for example sheet, cubic, hexagonal, orthorombic, etc.). Mention may be made of talc, mica, silica, kaolin, polyamide (Nylon®) (Orgasol® from Atochem), poly- ⁇ -alanine and polyethylene powders, powders of tetrafluoroethylene polymers (Teflon®) ), lauroyl-lysine, starch, boron nitride, expanded polymeric hollow microspheres such as those of polyvinylidene chloride / acrylonitrile such as Expancel® (Nobel Industry), of acrylic acid copolymers (Polytrap® of Dow Corning) and silicone resin microbeads (Tospearis® from Toshiba, for example), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate and hydro carbonate, hydroxyapatit
• composition according to the invention may also contain ingredients commonly used in cosmetics, such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestrants, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, fibers, hair loss agents, eyelash care agents, anti-dandruff agents, propellants, or mixtures thereof.
• ingredients commonly used in cosmetics such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestrants, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, fibers, hair loss agents, eyelash care agents, anti-dandruff agents, propellants, or mixtures thereof.
• fiber is meant an object of length L and of diameter D such that L is much greater than D, D being the diameter of the circle in which the section of the fiber is inscribed.
• L / D ratio (or form factor) is chosen from the range going from 3.5 to 2500, preferably from 5 to 500, and better still from 5 to 150.
• the fibers have a length ranging from 1 ⁇ m to 10 mm, preferably from 0J mm to 5 mm and better still from 0.3 mm to 3mm.
• the fibers which can be used in the composition of the invention can be chosen from rigid or non-rigid fibers, they can be of synthetic or natural, mineral or organic origin.
• the fibers can be present in the composition according to the invention in a content ranging from 0J to 10% by weight, better still from 0.5 to 5% by weight relative to the total weight of the composition.
• the gelling agents which can be used in the compositions according to the invention can be hydrophilic, lipophilic, organic or inorganic, polymeric or molecular gelling agents.
• mineral lipophilic gelling agent mention may be made of clays which may be modified, such as hectorites modified with ammonium chloride of C 10 to C 22 fatty acid, such as hectorite modified with di-stearyl dimethyl ammonium chloride such as that, for example, that marketed under the name of "Bentone 38V ® " by the company ELEMENTIS. Mention may also be made of fumed silica optionally treated hydrophobically at the surface, the particle size of which is less than 1 ⁇ m. It is indeed possible to chemically modify the surface of the silica, by chemical reaction generating a reduction in the number of silanol groups present on the surface of the silica.
• clays which may be modified, such as hectorites modified with ammonium chloride of C 10 to C 22 fatty acid, such as hectorite modified with di-stearyl dimethyl ammonium chloride such as that, for example, that marketed under the name of "Bentone 38V ® " by the company EL
• hydrophobic silica is then obtained.
• the hydrophobic groups can be: - Trimethylsiloxyl groups, which are obtained in particular by treatment of fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are called “Silica silylate” according to the CTFA (6 th edition, 1995).
• Hydrophobic fumed silica in particular has a particle size which can be nanometric to micrometric, for example ranging from approximately 5 to 200 nm.
• the polymeric organic lipophilic gelling agents are, for example, elastomeric polyorganosiloxanes partially or totally crosslinked, three-dimensional structure, such as those sold under the names "KSG6 ®", “KSG16 ®” and “KSG18 ®” by the company Shin-Etsu, for "Trefil E-505C ® “ and “Trefil E-506C ® “ by the company DOW-CORNING, from “Gransil SR-CYC ® ", "SR DMF10 ® “, “SR-DC556 ® “, “SR 5CYC gel ® “ , “SR DMF 10 gel ® “ and “SR DC 556 gel ® " by the company GRANT INDUSTRIES, "SF 1204 ® “ and “JK 113 ® “ by the company GENERAL ELECTRIC; the block copolymers of "diblock” or “triblock” of the polystyrene / polyisoprene or polystyrene
• lipophilic gelling agents which can be used in the compositions according to the invention, mention may also be made of dextrin and fatty acid esters, such as dextrin palmitates, in particular such as those marketed under the names of "Rheopearl TL ® " or “Rheopearl KL ®” by the company CHIBA FLOUR.
• silicone polyamides of the polyorganosiloxane type can belong to the following two families: 1) polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located in the polymer chain, and / or 2) polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located on grafts or ramifications.
• composition according to the invention comprises an aqueous medium
• it can comprise a hydrophilic or water-soluble gelling agent.
• hydrophilic or water-soluble gelling agents there may be mentioned: homo- or copolymers of acrylic or methacrylic acids or their salts and their esters and in particular the products sold under the names
• water-soluble gelling polymers examples include: proteins such as proteins of vegetable origin such as proteins from wheat, from soybeans; proteins of animal origin such as keratins, for example keratin hydrolysates and sulfonic keratins; anionic, cationic, amphoteric or nonionic chitin or chitosan polymers; non-fat-soluble cellulose polymers such as hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylhydroxyethylcellulose, carboxymethylcellulose, as well as quaternized derivatives of cellulose; vinyl polymers, such as polyvinylpyrrolidones, copolymers of methyl vinyl ether and malic anhydride, the copolymer vinyl acetate and crotonic acid, copolymers of vinylpyrrolidone and vinyl acetate; vinylpyrrolidone and caprolactam copolymers; polyvinyl alcohol; associative polyurethanes such
• solutions or dispersions of these associative polyurethanes in particular in water or in an alcoholic medium.
• such polymers include SER AD 1x1010, SER AD FX1035 and SER AD 1070 from the company SERVO DELDEN, Rheolate 255, Rheolate 278 and Rheolate 244 sold by the company RHEOX.
• polymers of natural origin possibly modified, such as: - gum arabic, guar gum, xanthan derivatives, karaya gum; alginates and carrageenans; glycoaminoglycans, hyaluronic acid and its
• the lipophilic or hydrophilic gelling agents can be present in the composition according to the invention in a content ranging from 0.05 to 40% by weight relative to the total weight of the composition, preferably from 0.5 to 20% and better still from 1 15% by weight.
• the composition according to the invention may contain emulsifying surfactants present in particular in a proportion ranging from 0.5 to 30% by weight relative to the total weight of the composition, better from 1 to 15% and better still from 3 to 10%. These surfactants can be chosen from anionic, cationic or nonionic surfactants.
• surfactants which can be used in the composition according to the invention:
• a) nonionic surfactants with an HLB greater than or equal to 8 at 25 ° C. used alone or as a mixture; mention may in particular be made of: oxyethylenated and / or oxypropylenated ethers (which may contain from 1 to 150 oxyethylenated and / or oxypropylenated groups) of glycerol; oxyethylenated and / or oxypropylenated ethers (which may contain from 1 to 150 oxyethylenated and / or oxypropylenated groups) of fatty alcohols (in particular C8-C24, and preferably C12-C18 alcohol) such as oxyethylenated ether cetearyl alcohol with 30 oxyethylenated groups (CTFA name "Ceteareth-30”) and the oxyethylenated ether of the mixture of C12-C15 fatty alcohols comprising 7 oxyethylenated groups (CT
• dimethicone copolyol such as that sold under the name "Q2-5220” by the company DOW CORNING; - dimethicone copolyol benzoate (FINSOLV SLB 101 and 201 from FINTEX); the copolymers of propylene oxide and of ethylene oxide, also called polycondensates OE / Op like for example the polyblock polyethylene glycol / polypropylene glycol / polyethylene glycol polycondensates sold under the names "SYNPERONIC” like "SYNPERONIC PE / L44” and " SYNPERONIC PE / F127 "by the company ICI, and mixtures thereof. and their mixtures.
• nonionic surfactants of HLB below 8 to 25 ° C optionally combined with one or more nonionic surfactants of HLB above 8 to 25 ° C, as mentioned above such as: esters and ethers daring such as sucrose stearate, sucrose cocoate, sorbitan stearate and their mixtures such as Arlatone 2121 sold by the company ICI; esters of fatty acids (in particular of C8-C24, and preferably of C16-C22) and of polyol, in particular of glycerol or of sorbitol, such as glyceryl stearate, glyceryl stearate such as the product sold under the name TEGIN M by the company GOLDSCHMIDT, glyceryl laurate such that the product sold under the name IMWITOR 312 by the company HULS, polyglyceryl-2 stearate, sorbitan tristearate, glyceryl ricinoleate; the mixture of cyclomethi
• Anionic surfactants such as: the salts of C 16 -C 30 fatty acids, in particular those derived from amines, such as triethanolamine stearate; the salts of polyoxyethylenated fatty acids, in particular those derived from amines or the alkaline salts, and their mixtures; - phosphoric esters and their salts such as "DEA oleth-10 phosphate” (Crodafos N 10N from the company CRODA); sulfosuccinates such as "Disodium PEG-5 citrate lauryl sulfosuccinate” and “Disodium ricinoleamido MEA sulfosuccinate” alkyl ether sulfates such as sodium lauryl ether sulfate; - isethionates; acylglutamates such as "Disodium hydrogenated tallow glutamate” (AMISOFT HS-21 R sold by the company AJINOM
• triethanolamine stearate is particularly suitable for the invention.
• the latter is generally obtained by simple mixing of stearic acid and triethanolamine.
• Surfactants are preferably used which make it possible to obtain an oil-in-water or wax-in-water emulsion.
• the composition according to the invention can be in particular in the form of a suspension, dispersion, solution, gel, emulsion, in particular oil-in-water (O / W) or water-in-oil (W / O) emulsion ), or multiple (W / O / W or polyol / O / W or O / W / O), in the form of a cream, paste, foam, vesicle dispersion, in particular of ionic lipids or not, of two-phase lotion or multiphase, spray, powder, paste, especially flexible paste.
• the composition may be anhydrous, for example it may be a paste or an anhydrous stick.
• the composition can be a leave-in composition.
• the composition according to the invention can be in particular in the form of a stick, suspension, dispersion, solution, gel, emulsion, in particular oil-in-water (O / W) or water-in-oil emulsion ( W / O), or multiple (W / O / W or polyol / O / W or O / W / O), in the form of a cream, paste, foam, vesicle dispersion, in particular of ionic lipids or not, of biphasic or multiphase lotion, of spray, powder, paste, in particular flexible paste (in particular paste having dynamic viscosity at 25 ° C of the order of 0J to 40 Pa.s under a shear speed of 200 s " 1 , after 10 minutes of measurement in cone / plane geometry)
• the composition may be anhydrous, for example it may be an anhydrous paste.
• composition according to the invention can be a makeup composition such as products for the complexion (foundations), blushes or eyeshadows, lipstick sticks, concealer products, blushes, mascaras , eyeliners, eyebrow makeup products, lip or eye pencils, nail products, such as nail polish, body makeup products, hair makeup products (mascara or hair spray).
• a makeup composition such as products for the complexion (foundations), blushes or eyeshadows, lipstick sticks, concealer products, blushes, mascaras , eyeliners, eyebrow makeup products, lip or eye pencils, nail products, such as nail polish, body makeup products, hair makeup products (mascara or hair spray).
• composition according to the invention can also be a product for caring for the skin of the body and the face, in particular a sunscreen product or for coloring the skin (such as a self-tanner).
• the invention relates to a composition for coating keratin fibers (such as the eyelashes, the eyebrows, the hair)
• compositions can be in different forms: for example, in the form of two-phase wax-in-water or water-in-wax emulsions, aqueous or anhydrous dispersions.
• the composition can be a makeup product for keratin fibers such as the eyelashes (mascara), a makeup product for the lips or the skin.
• the subject of the invention is a cosmetic composition
• a cosmetic composition comprising, in a cosmetically acceptable medium, a liquid fatty phase and a modified liposoluble cellulose or cellulose ester, said cellulose or said modified cellulose ester comprising replaced free hydroxyl functions , in whole or in part, by hydrophobic groups chosen from the radicals of formula -OYR, in which: - R represents a group chosen from: A) hydrocarbon groups with straight or branched chains, saturated or unsaturated, or cyclic saturated or unsaturated , comprising from 8 to 50 carbon atoms for the modified cellulose or from 4 to 50 carbon atoms for the modified cellulose ester, the said groups being able to contain in their chains one or more aromatic groups and / or one or more heteroatoms chosen from O, N, P, Si, S; said groups possibly being fluorinated or perfluorinated;
• the invention relates to an anhydrous cosmetic composition
• an anhydrous cosmetic composition comprising, in a cosmetically acceptable medium, a phase liquid fatty acid and at least 4% of a liposoluble modified cellulose derivative, said modified cellulose derivative comprising free hydroxyl functions replaced, in whole or in part, by hydrophobic groups chosen from the radicals of formula -OYR, in which: R represents a group chosen from: A) hydrocarbon groups with straight or branched chains, saturated or unsaturated, or saturated or unsaturated cyclic chains of 4 to 50 carbon atoms for the modified cellulose derivative, said groups possibly comprising in their chains one or several aromatic groups and / or one or more heteroatoms chosen from O, N, P, Si, S; said groups possibly being fluorinated or perfluorinated;
• the present invention also relates to a cosmetic assembly comprising:
• composition as described above arranged inside said compartment.
• the container can be in any suitable form. It can in particular be in the form of a bottle, a tube, a pot, a case, a box, a sachet or a case.
• the closure element may be in the form of a removable stopper, a cover, a cover, a tearable strip, or a capsule, in particular of the type comprising a body fixed to the container and an articulated cap. on the body. It can also be in the form of an element ensuring the selective closure of the container, in particular a pump, a valve, or a valve.
• the container can be associated with an applicator, in particular in the form of a brush comprising an arrangement of bristles held by a twisted wire. Such a twisted brush is described in particular in US Pat. No. 4,887,622. It can also be in the form of a comb comprising a plurality of application elements, obtained in particular by molding.
• the applicator can be in the form of a brush, as described for example in patent FR 2 722 380.
• the applicator can be in the form of a block of foam or elastomer, a felt, or a spatula.
• the applicator can be free (puff or sponge) or integral with a rod carried by the closure element, as described for example in US patent 5,492,426.
• the applicator can be integral with the container, as described for example the patent FR 2 761 959.
• the product can be contained directly in the container, or indirectly.
• the product can be placed on an impregnated support, in particular in the form of a wipe or a tampon, and placed (individually or several) in a box or in a sachet.
• an impregnated support in particular in the form of a wipe or a tampon
• Such a support incorporating the product is described for example in application WO 01/03538.
• the closure element can be coupled to the container by screwing.
• the coupling between the closure element and the container is done other than by screwing, in particular via a bayonet mechanism, by snap-fastening, tightening, welding, bonding, or by magnetic attraction.
• snap-fastening is meant in particular any system involving the crossing of a bead or a bead of material by elastic deformation of a portion, in particular of the closure element, then by return to the unstressed position of said elastic portion after crossing the bead or cord.
• the container can be at least partly made of thermoplastic material. Mention may be made, as examples of thermoplastic materials, of polypropylene or polyethylene.
• the container is made of non-thermoplastic material, in particular glass or metal (or alloy).
• the container may have rigid walls or deformable walls, in particular in the form of a tube or a tube bottle.
• the container may include means for causing or facilitating the distribution of the composition.
• the container may have deformable walls so as to cause the exit of the composition in response to an overpressure inside the container, which overpressure is caused by elastic (or inelastic) crushing of the walls of the container. .
• the latter can be driven by a piston mechanism.
• the container may include a mechanism, in particular rack and pinion, or with a threaded rod, or with a helical ramp, and able to move a stick in the direction of said opening.
• a mechanism is described for example in patent FR 2 806 273 or in patent FR 2 775 566.
• Such a mechanism for a liquid product is described in patent FR 2 727 609.
• the container may consist of a housing with a bottom delimiting at least one housing containing the composition, and a cover, in particular articulated on the bottom, and capable of covering said bottom at least in part.
• a cover in particular articulated on the bottom, and capable of covering said bottom at least in part.
• the container can be equipped with a wringer disposed near the opening of the container.
• a wringer makes it possible to wipe the applicator and possibly, the rod of which it may be integral.
• Such a wringer is described for example in patent FR 2 792 618.
• the composition can be at atmospheric pressure inside the container (at room temperature) or pressurized, in particular by means of a propellant gas (aerosol). In the latter case, the container is fitted with a valve (of the type used for aerosols).
• Example 1 Preparation of a cellulose acetobutyrate with isostearyl ester side groups.
• cellulose acetate butyrate CAB 553-0,4 from EASTMAN comprising
• 1800 g of a solvent mixture consisting of 900 g of methyl ethyl ketone and 900 g of toluene are introduced into a 3 I reactor with central stirring, refrigerant and introduction of nitrogen.
• the isostearyl chloride solution is introduced dropwise while maintaining the internal temperature at + 10 ° C.
• the duration of introduction is 1 h 30.
• the mixture is allowed to return to stirring at ambient temperature and the reaction is maintained for 18 hours.
• the triethylamine hydrochloride formed precites in the medium.
• the purified solution obtained is filtered by precipitation, at room temperature and with stirring in 10 liters of absolute ethanol.
• the polymer precipitate obtained is recovered and dried under vacuum to constant weight. 145 g of dried polymer are thus obtained.

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• 2003
  • 2003-07-07 FR FR0350299A patent/FR2857257B1/fr not_active Expired - Fee Related
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