Compositions containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one, a preservative and / or antioxidant, a surfactant and a polymer, and methods of treating keratin materials using the compositions

Abstract

The present invention relates to a composition comprising i) at least one 4-(3-ethoxy-4- hydroxyphenyl)butan-2-one compound; ii) at least one preservative and / or antioxidant different from i); iii) at least one surfactant chosen from surfactants; iv) at least one polymer, preferably organic, especially a thickening polymer; and v) optionally a fatty substance. The present invention also relates to the use of i) to vi) as antimicrobial agents, to a method for treating keratin materials using a composition comprising i) to vi), and to a kit comprising ingredients i) to vi). The combination of i), ii), iii), iv) and optionally v) makes it possible to obtain an antimicrobial mixture with excellent antimicrobial activity, in particular against Aspergillus niger, Escherichia coli, Staphylococcus aureus and Candida albicans. Furthermore, the formulation remains stable over time, while at the same time retaining antimicrobial activity over time, even after 7 days, 15 days, 1 month and at room temperature.

Description

[0001] This invention relates to a composition comprising i) at least one 4-(3-ethoxy-4-hydroxyphenyl)but-2-one; ii) at least one preservative and / or at least one antioxidant other than i); iii) at least one surfactant; iv) at least one polymer, preferably organic, especially a thickening polymer; and v) optionally a fatty substance, and it should be understood that when the composition contains cationic surfactants, their concentration is less than 3% by weight relative to the total weight of the composition. The invention also relates to the use of i) to vi) as an antimicrobial agent, to a method for treating keratin materials with a composition comprising i) to vi), and to a cassette comprising components i) to vi). Technical Field

[0002] Microorganisms can survive and multiply in cosmetics, pharmaceuticals, and food products that do not contain preservatives. Preservatives are regularly added to all industrial formulations intended for storage or preservation to prevent microbial growth over time.

[0003] Microbial contamination is common during the production of industrial products, even when the starting ingredients are "clean," meaning there are no contaminating microorganisms present. For example, water, prevalent in most cosmetic, pharmaceutical, or food products, must be free of contaminating microorganisms. All other ingredients must also be screened for the presence of contaminating microorganisms. Cleanliness, handling of contents, and container filling during the production of these industrial products must be rigorously monitored. Despite these precautions, the microbial integrity of a product may require the presence of one or more preservatives compatible with the product and the stability of the composition. The product must not allow the growth or viability of contaminating microorganisms. Furthermore, maintaining cleanliness during use remains problematic because fingers, cosmetic applicators, and even ambient air are not sterile. Therefore, preservatives are needed to reduce microbial contamination for consumers during normal use.

[0004] Generally, all products sold (especially cosmetic products) must be free of pathogenic microorganisms (Kirk-Othmer Encyclopedia, Cosmetics, Martin M. Rieger, 04 / 12 / 2000; https: / / doi.org / 10.1002 / 0471238961.0315191318090507.a01). In recent years, preservation issues have also led to the introduction of preservatives, the range of which covers those resistant to contaminating microorganisms.

[0005] Furthermore, it appears that some commonly used preservatives are inactivated by a variety of surfactants. The more hydrophobic a preservative is, the greater the risk of it being trapped in organized molecular systems (such as micelles), and subsequently becoming less effective or even ineffective against microorganisms (especially pathogens) (Ullmann's Encyclopedia of Industrial Chemistry, "Skin Cosmetics", G. Schneider et al., Vol. 33, p. 221, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim DOI:10.1002 / 14356007.a24_219).

[0006] Therefore, the development of new antimicrobial combinations to address these challenges has generated considerable interest.

[0007] 4-(3-ethoxy-4-hydroxyphenyl)but-2-one or ethyl gingerone (EZ) are known components as preservatives (for protecting the composition from microbial contamination) used in compositions, particularly cosmetic compositions (see, for example, WO 2011 / 039445). These compounds have been used alone or in mixtures with other preservative or non-preservative compounds (see, for example, WO 2018 / 115058). Where possible, there is great interest in using such preservatives in compositions, particularly in cosmetic or pharmaceutical compositions, and especially in dermatological compositions, at a reduced concentration preferably less than 1% by weight relative to the total weight of the composition containing the preservative. These preservatives not only possess the same or even enhanced antimicrobial activity but are also stable in the composition over time, while avoiding odor changes over time, and retaining their ability as a preservative, i.e., their antimicrobial efficacy. FR 1 756 156 and WO 2019 / 002 400 also describe cosmetic compositions containing EZ and another type of aromatic alcohol preservative. These compositions do not always provide a satisfactory appearance, especially in terms of matte and / or soft-focus effects after application to the skin, and also in terms of formulation stability, particularly with respect to temperature.

[0008] Furthermore, compositions containing several antimicrobial agents have generated considerable interest, which remain stable in formulation and are not overly viscous, i.e., less than 90 poise, preferably less than 45 poise. Compositions that do not change over time, particularly in appearance and / or viscosity, even after storage at temperatures greater than or equal to 25°C, especially 37°C to 45°C, and / or at temperatures below 25°C, especially 1°C to 10°C, such as 4°C, for several weeks or even months, are also sought.

[0009] In addition, compositions intended for application to keratin materials, especially the skin, must have a matte or even a non-greasy finish after application.

[0010] In terms of the sensation of the composition to be applied to keratin materials, a sufficiently long-lasting pleasant application effect is generally sought, which may also be accompanied by a refreshing sensation.

[0011] It has been unexpectedly discovered that the following mixtures enable the preparation of an antimicrobial mixture that improves or even synergizes antimicrobial activity while maintaining the physicochemical stability of the formulation over time; a mixture of the following: i) at least one 4-(3-ethoxy-4-hydroxyphenyl)but-2-one or its organic or inorganic base salt, and its solvates such as hydrates; ii) at least one preservative and / or at least one antioxidant other than i); iii) at least one surfactant; iv) at least one thickening polymer, preferably organic; and v) optionally at least one aliphatic substance, which is particularly liquid at room temperature and atmospheric pressure. It should be understood that when the mixture contains one or more cationic surfactants, their amounts are less than 3% by weight relative to the total weight of components i) to v). Furthermore, it can be seen that compositions comprising components i) to iv) and optionally v) as defined below remain stable even after several weeks or even months at room temperature or even at temperatures above 25°C (37°C and 45°C). Furthermore, it can be seen that neither the combination of components i) to iv) and optionally v) nor the composition itself showed any odor change or unpleasant odor over time.

[0012] Furthermore, the viscosity of the compositions of the present invention is sufficient for good application to keratin materials and / or is stable over time. Application to keratin materials, especially the skin, is pleasant, particularly when the composition is applied by circular motions of the fingers over the skin. A pleasantly refreshing feeling can even be felt on the skin during application.

[0013] The subject of this invention is also a composition, particularly a cosmetic composition, comprising the ingredients i) to iv) and optionally v) as defined above, and it should be understood that the composition comprises a cationic surfactant in an amount of less than 0.5% by weight relative to the total weight of the composition.

[0014] The subject of this invention is also a method for non-therapeutic cosmetic treatment of keratin materials, comprising applying a composition, particularly a cosmetic composition, to the keratin material, especially human keratin material such as skin, comprising components i) to iv) and optionally v) as defined above. This method can be a cosmetic approach for treating, applying makeup, dispensing fragrance, or cleansing keratin materials.

[0015] The subject of this invention is also a method for preserving compositions, particularly cosmetic or pharmaceutical compositions, that contain physiologically acceptable media, characterized in that the method comprises incorporating the composition with an antimicrobial mixture as defined above (i) to (iv) and optionally (v).

[0016] The results of the following examples demonstrate that, based on minimum inhibitory concentration (MIC) measurements using several mixtures, the antimicrobial activity of combinations of i), ii), iii), and iv) as described above, as well as optionally v), was improved compared to i) or ii) alone in equivalent amounts.

[0017] Combinations of i), ii), iii), iv), and optionally v) enable the production of antimicrobial mixtures exhibiting particularly excellent antimicrobial activity against Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans. Furthermore, the compositions remain stable over time, even after 7 days, 15 days, or 1 month at room temperature, while simultaneously maintaining their antimicrobial activity over time.

[0018] More precisely, the subject of this invention is an antimicrobial mixture comprising or consisting of (or composed of) the following as defined above: i), ii), iii) and iv), and optionally v), wherein the combination is 80% to 90% by weight relative to the total weight of the combination.

[0019] For the purposes of this invention and unless otherwise stated:

[0020] The term "thickening polymer" means a polymer that, when introduced at 1% by weight into an aqueous solution or an aqueous-alcoholic solution containing 30% ethanol at pH 7, or into a mixture selected from liquid petrolatum, isopropyl myristate, or cyclopentadimethylsiloxane, enables the thickening polymer to be applied at 25°C and within 1 second. -1The viscosity should be at least 100 cps, and preferably at least 500 cps, at a given shear rate. This viscosity can be measured using a cone / plate viscometer (Haake R600 rheometer, etc.). The thickening polymer can thicken the aqueous phase and / or the aliphatic phase, preferably the aqueous phase.

[0021] The term "organic thickening polymer" means a thickening polymer as defined above, which is formed of carbon and hydrogen, and possibly nitrogen, oxygen, sulfur, halogens (such as fluorine, chlorine, or bromine), and also phosphorus, alkali metals (such as sodium or potassium), or alkaline earth metals (such as magnesium or calcium). The organic polymers according to the invention do not contain silicon;

[0022] - According to the present invention, the term "non-cellulose-based organic thickening polymer" means an organic thickening polymer that does not contain any cellulose units;

[0023] - The term "surfactant" means "surface agent," which is a compound that can change the surface tension between two surfaces; surfactants are amphiphilic molecules, that is, they contain two parts with different polarities, one lipophilic and nonpolar, and the other hydrophilic and polar.

[0024] For the purposes of this invention, the term "aliphatic substance" means an organic compound that is insoluble in water (solubility less than 5%, preferably less than 1%, and even more preferably less than 0.1%) at room temperature (25°C) and atmospheric pressure (760 mmHg); in addition, aliphatic substances are soluble in organic solvents under the same temperature and pressure conditions, such as halogenated solvents (e.g., chloroform or dichloromethane), lower alcohols (e.g., ethanol), or aromatic solvents (e.g., benzene or toluene);

[0025] - The term "organic or inorganic acid salt" more specifically means a salt selected from the following salts derived from: i) hydrochloric acid (HCl); ii) hydrobromic acid (HBr); iii) sulfuric acid (H2SO4); iv) alkyl sulfonic acids: Alk-S(O)2OH, such as methanesulfonic acid and ethanesulfonic acid; v) aryl sulfonic acids: Ar-S(O)2OH, such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-OS(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids, such as toluenesulfinic acid and phenoxysulfinic acid; xii) phosphoric acid (H3PO4); xiii) acetic acid (CH3C(O)OH); xiv) trifluoromethanesulfonic acid (CF3SO3H); and xv) tetrafluoroborate (HBF4);

[0026] - The term "organic or inorganic alkali salt" means a salt of an alkaline base or alkaline agent as defined below, such as alkali metal hydroxides (e.g., sodium hydroxide or potassium hydroxide), ammonia, amines or alkanolamines;

[0027] - The term "cation counterion" refers to a cation or a cation group derived from an organic or inorganic alkali salt that balances the anionic charge of the components of formula (I′) or (II′); more specifically, the cation counterion is selected from i) alkali metals such as sodium and potassium, preferably Na; ii) alkaline earth metals such as calcium; iii) ammonium R4N + R can be the same or different, representing a hydrogen atom or an alkyl group (C1-C6) optionally substituted with one or more hydroxyl groups; preferably, R represents a hydrogen atom or an alkyl group (C1-C4) such as methyl.

[0028] - When it includes one or more double bonds and / or one or more triple bonds that can be conjugated, the hydrocarbon-based chain is "unsaturated" or the (hetero)cyclic group is "unsaturated";

[0029] - "alkyl" refers to a saturated straight-chain or branched C1-C group. 20 Preferably C1-C6, more preferably based on C1-C4 hydrocarbon groups, such as methyl or ethyl;

[0030] - "alkylene" is an unsaturated divalent hydrocarbon-based group as previously defined, which may contain 1 to 4 conjugated or non-conjugated double bonds -C=C-; alkenyl groups in particular contain 1 or 2 degrees of unsaturation;

[0031] - The expression “optionally substituted” given to an alkyl group means that the alkyl group may be substituted by one or more groups selected from the following groups: i) hydroxyl, ii) C1-C4 alkoxy, iii) amide, iv) amino group optionally substituted by one or two identical or different C1-C4 alkyl groups;

[0032] - "alkoxy" is an alkyl-oxy group, where the alkyl group is a straight-chain or branched C1-C group. 16 Preferably based on C1-C8 hydrocarbon groups; - The expression "at least one (kind)" is equivalent to "one (kind) or more (kinds)";

[0033] - A "heterocyclic" group is a 5- to 12-membered ring group based on a hydrocarbon, whether saturated or unsaturated, aromatic or non-aromatic, monocyclic or polycyclic, containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen, which form part of at least one ring member of the ring; in particular, the heterocyclic group is selected from morpholino, piperazine, piperidinyl, furanyl, pyridinyl, indolyl, and (benzo)imidazolyl.

[0034] - "Cycloalkyl" is a saturated or unsaturated, non-aromatic, monocyclic or polycyclic 4- to 14-membered hydrocarbon-based group, which includes 4 to 14 carbon atoms, such as cyclobutyl, cyclopentyl and cyclohexyl.

[0035] - "aryl" is an unsaturated, aromatic, monocyclic or polycyclic 6- to 14-membered hydrocarbon-based group comprising 6 to 14 carbon atoms, such as phenyl or diphenyl, preferably phenyl;

[0036] - The term "inclusive" for concentration range means that the limits of the range are included within the defined interval.

[0037] i)4-(3-ethoxy-4-hydroxyphenyl)but-2-one It is a compound of formula (I):

[0038] [Chemical Formula 1]

[0039]

[0040] i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one can be found in solvated form, especially in hydrated form.

[0041] i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one can be found in the form of organic or inorganic base salting according to formula (I'):

[0042] [Chemical Formula 2]

[0043]

[0044] In equation (I'), M + It indicates a cation counterion, especially alkali metals such as sodium or potassium, alkaline earth metals such as calcium, or ammonium.

[0045] ii) Preservatives and / or antioxidants

[0046] According to a specific embodiment of the present invention, component ii) represents one or more preservatives.

[0047] It should be understood that “preservative” ii) is different from preservative as defined above in i).

[0048] The term "preservative" or "preserving agent" means any cosmetically or pharmaceutically acceptable compound that prevents the growth (or microbial growth) of microorganisms that may occur in a cosmetic or pharmaceutical composition, from the time the composition is prepared, while it is stored, and until it is used regularly by the consumer. Preservatives that may be specifically mentioned include those described in: Cosmetics, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, Inc., Martin M. Rieger; 5.2 Preservatives and Table 3, 04 / 12 / 2000, https: / / doi.org / 10.1002 / 0471238961.0315191318090507.a01.

[0049] According to specific embodiments, the preservative is selected from organic preservatives containing aromatic groups.

[0050] Preferably, the preservative, unlike i), is selected from: a) benzene-based carboxylic acids, wherein the phenyl group is optionally substituted with one or more groups selected from: hydroxyl, (C1-C2)... 10 )alkyl and (C1-C 10 ) alkyl carbonyl groups, and their base salts, especially alkali metal salts and alkaline earth metal salts; b) hydroxybenzoic acid esters, which optionally have one or more groups selected from the group consisting of: (C1-C2) alkyl carbonyl groups, and their base salts, especially alkali metal salts and alkaline earth metal salts; 10 (i) Alkyl groups such as parabens, especially methylparaben, ethylparaben, propylparaben and butylparaben; (ii) Aromatic alcohols; preferably, the preservatives other than (i) are selected from (a), and in particular benzoic acid [65-85-O], and also its base salts, especially alkali metal salts and alkaline earth metal salts; and also salicylic acid optionally substituted with (C1-C8) alkyl carbonyl groups, preferably salicylic acid.

[0051] According to another embodiment, the preservative ii) is different from i) and is selected from aromatic alcohols c) such as phenoxyethanol.

[0052] According to another advantageous embodiment of the invention, component ii) represents one or more antioxidants.

[0053] The term "antioxidant" refers to any cosmetic or pharmaceutically acceptable compound that prevents or slows down the oxidation of other ingredients upon contact with it. Oxidation can occur in cosmetic or pharmaceutical compositions from the moment the composition is prepared, during their storage, and until they are used regularly by consumers, especially due to the presence of atmospheric oxygen, radiation, and in-situ formation of free radicals. Antioxidants that may be specifically mentioned include those described in the following: Cosmetics, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, Inc., Martin M. Rieger; 5.1 Antioxidants and Table 2. Free-Radical-Inhibiting Antioxidants or Reductants Useful in Cosmetics, 04 / 12 / 2000 https: / / doi.org / 10.1002 / 0471238961.0315191318090507.a01

[0054] Preferably, the antioxidant is selected from ketone and / or carboxyl heterocyclic acid compounds, such as caffeine, amino acids and hydroxylated benzene compounds, which are optionally substituted with one or more (C1-C4) alkyl groups on the benzene ring, especially from benzene-based alcohols, preferably hydroxyacetophenone.

[0055] According to a preferred embodiment of the present invention, the antioxidant ii) is selected from 4-hydroxyacetophenone (also known as 4-hydroxyphenylacetophenone), p-acetylphenol, p-hydroxyphenylmethyl ketone, or physalicylic acid, which is a compound of formula (II):

[0056] [Chemical Formula 3]

[0057]

[0058] 4-Hydroxyacetophenone can be in a solvated form, especially in a hydrated form.

[0059] 4-Hydroxyacetophenone can be found in the form of organic or inorganic base salts of the following formula (II'):

[0060] [Chemical Formula 4]

[0061]

[0062] In equation (II'), M + It indicates a cation counterion, especially alkali metals such as sodium or potassium, alkaline earth metals such as calcium, or ammonium.

[0063] According to another specific embodiment of the invention, component ii) represents a mixture of one or more preservatives and one or more antioxidants as defined above, particularly a mixture of a preservative selected from aromatic alcohols c) (such as phenoxyethanol) and an antioxidant selected from ketone and / or carboxyl heterocyclic acid compounds (such as caffeine).

[0064] According to another advantageous embodiment of the invention, component ii) represents one or more compounds that are preservatives and antioxidants.

[0065] According to specific embodiments of the present invention, i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one and component ii) in particular 4-hydroxyacetophenone are present in the mixture or composition in a certain amount, such that the weight ratio i) / ii) ranges from 0.05 to 5, preferably from 0.08 to 5, more preferably from 0.08 to 0.25, and from 2 to 4, more preferably from 0.15 to 0.25, and from 3 to 3.8. This mixture exhibits good antimicrobial activity against molds, especially against Aspergillus niger.

[0066] Advantageously, i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one and component ii) in particular 4-hydroxyacetophenone are present in the mixture or composition in a certain amount, such that the weight ratio i) / ii) ranges from 0.08 to 0.5, preferably from 0.08 to 0.3, more preferably from 0.08 to 0.25, and more preferably from 0.15 to 0.25. This mixture exhibits good antimicrobial activity against molds, especially against Aspergillus niger.

[0067] According to another specific embodiment of the invention, i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one and component ii) in particular 4-hydroxyacetophenone are present in the mixture or composition in a certain amount such that the weight ratio i) / ii) ranges from 0.5 to 5, preferably from 1 to 4, and more preferably from 3 to 3.8. This mixture exhibits good antimicrobial activity against Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans, and this remains true over time, even after several weeks (one week, two weeks, or even one month).

[0068] iii) Surfactants

[0069] The mixtures of the present invention comprise the ingredients i) to iv) and optionally v) as defined above. It should be understood that when the mixture contains one or more cationic surfactants, the amount of which is less than 3% by weight, preferably less than or equal to 2% by weight, more particularly less than or equal to 1% by weight, and even more preferably less than 0.5% by weight, of the cationic surfactant relative to the total weight of the composition; and even more preferably, the mixture does not contain any cationic surfactants.

[0070] The compositions of the present invention comprise iii) one or more surfactants selected from the group consisting of nonionic, anionic, amphoteric, or amphoteric or cationic surfactants. It should be understood that the composition comprises 0.5% by weight, preferably less than or equal to 0.2% by weight, and even more particularly less than or equal to 0.1% by weight relative to the total weight of the composition; even more preferably, the composition comprises less than 0.05%; and even more preferably, the compositions of the present invention do not contain any cationic surfactants. According to a preferred embodiment of the invention, the surfactant is nonionic or anionic, preferably nonionic.

[0071] In the nonionic surfactants according to the invention, reference may be made to a) fatty alcohols, b) α-diols and c) alkylphenols, either alone or as mixtures, wherein these three types of compounds a) to c) are polyethoxylated, polypropoxylated and / or polyglycerolized and contain a fatty chain comprising, for example, 8 to 30 carbon atoms, particularly 10 to 22 carbon atoms, wherein the number of ethyleneoxy or propyleneoxy groups may range particularly from 2 to 200, particularly from 10 to 100 and the number of glycerol groups may range particularly from 2 to 200, particularly from 10 to 100. Also mentioned are copolymers of ethylene oxide (EO) and propylene oxide (PO), condensates of ethylene oxide and propylene oxide with fatty alcohols; preferably polyethoxylated fatty amides having 2 to 30 mol of EO, including polyglycerolized fatty amides with an average of 1 to 5, and particularly 1.5 to 4, glycerol groups; oxyethylated fatty acid esters of anhydrous sorbitol containing 2 to 200 mol of EO, particularly 10 to 100 mol of EO; fatty acid esters of sucrose, fatty acid esters of polyethylene glycol, alkyl polyglycosides, N-alkyl glucosamine derivatives, amine oxides such as (C 10 -C 14 Alkylamine oxide or N-acylaminopropylmorpholine oxide.

[0072] Preferably, the nonionic surfactant is selected from: (poly)ethoxylated fatty alcohols; glycerolized fatty alcohols; alkyl polyglycosides, preferably oxyethylated fatty acid monoesters and diesters containing 2 to 200 mol of EO, particularly 10 to 100 mol of sorbitol.

[0073] More preferably, the surfactant is selected from oxyethylated fatty acid monoesters and diesters containing 2 to 200 mol of EO, particularly 10 to 100 EO of dehydrated sorbitol, such as propylene glycol stearate, glyceryl monostearate / glyceryl distearate / polyethylene glycol stearate (100 EO) containing 10 to 30 EO, such as 20 EO.

[0074] The term "fatty chain" refers to a straight or branched, saturated or unsaturated hydrocarbon-based chain containing 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms, such as stearyl groups.

[0075] Regarding alkyl polyglycosides, these compounds are well known and can be more specifically represented by the following general formula: R1O-(R2O) t (G) v (III), in equation (III):

[0076] -R1 indicates a straight-chain or branched alkyl and / or alkenyl group comprising about 8 to 24 carbon atoms, or a straight-chain or branched alkyl group comprising an alkylphenyl group comprising 8 to 24 carbon atoms;

[0077] -R2 indicates an alkylene group consisting of approximately 2 to 4 carbon atoms;

[0078] -G indicates a sugar unit consisting of 5 to 6 carbon atoms;

[0079] -t is 0 to 10 and includes endpoints, preferably 0 to 4, preferably an integer from 0 to 4; and

[0080] -v indicates an integer from 1 to 15 including the end value.

[0081] Preferred alkyl polyglycosides according to the invention are compounds of formula (III), wherein R1 more particularly indicates a straight-chain or branched, saturated or unsaturated alkyl group comprising 8 to 18 carbon atoms, t indicates a value ranging from 0 to 3 and more particularly equal to 0, and G may indicate glucose, fructose, or galactose, preferably glucose. The degree of polymerization, i.e., the value of v in formula (III), can range from 1 to 15 and preferably from 1 to 4. The average degree of polymerization is more particularly from 1 to 2 and even more preferably from 1.1 to 1.5.

[0082] The glycosidic bonds between these sugar units are of type 1-6 or 1-4, and preferably of type 1-4.

[0083] Compounds of formula (III), especially those produced by Cognis under the name... (600CS / U, 1200 and 2000) or Products sold under the names (818, 1200, and 2000) are representative. Also available are those from SEPPIC under the names Triton CG 110 (or Oramix CG 110) and Triton CG 312 (or...). Products sold by NS 10, products sold by BASF under the name Lutensol GD 70, or products sold by Chem Y under the name AG10 LK.

[0084] You can also use, for example (C8 / C 16 Alkyl-1,4-polyglucoside as a 53% aqueous solution was supplied by Corning under index number [index number missing]. 818UP for sale.

[0085] Regarding monoglyceride or polyglyceride surfactants, they preferably comprise an average of 1 to 40 glycerol groups, more particularly 10 to 30 glycerol groups, such as 20.

[0086] According to specific embodiments of the present invention, the surfactant is monoglyceridated or polyglyceridated, and is preferably selected from compounds having the following formula:

[0087] RO[CH2CH(CH2OH)O] m H,

[0088] RO[CH2CH(OH)CH2O] m H or

[0089] RO[CH(CH2OH)CH2O] m H;

[0090] In these formulas:

[0091] -R represents a straight-chain or branched, saturated or unsaturated hydrocarbon-based group comprising 8 to 40 carbon atoms, preferably 10 to 30 carbon atoms;

[0092] -m is a number from 1 to 30, preferably from 1 to 10, and more particularly from 1.5 to 6. R may optionally contain heteroatoms, such as oxygen and nitrogen. In particular, R may optionally contain one or more hydroxyl and / or ether and / or amide groups. R preferably indicates a C that is optionally monohydroxylated or polyhydroxylated. 10 -C 20 Alkyl and / or alkenyl groups.

[0093] Preferably, the compositions of the present invention comprise one or more (poly)ethoxylated fatty alcohols suitable for carrying out the present invention, more particularly selected from alcohols comprising 8 to 30 carbon atoms, and preferably 12 to 22 carbon atoms.

[0094] (Poly)ethoxylated fatty alcohols particularly contain one or more straight-chain or branched, saturated or unsaturated hydrocarbon-based groups comprising 8 to 30 carbon atoms, optionally substituted, particularly substituted by one or more (especially 1 to 4) hydroxyl groups. If they are unsaturated, these compounds may contain one to three conjugated or non-conjugated carbon-carbon double bonds.

[0095] (Poly)ethoxylated fatty alcohols preferably have the following formula:

[0096] R a -[O-CH2-CH2] n -OH

[0097] and

[0098] -R a C1-C represents a straight chain or a branched chain. 40 Alkyl or straight-chain or branched C2-C 30 alkenyl (preferably C8-C) 30 Alkyl); and

[0099] -n represents an integer including end values ​​of 1 to 200, preferably 2 to 100, more particularly including end values ​​of 10 to 50, and even more particularly including end values ​​of 15 to 30, such as 100 or 20.

[0100] (Poly)ethoxylated fatty alcohols are more particularly fatty alcohols comprising 8 to 22 carbon atoms and oxyethylated with 1 to 30 mol of ethylene oxide (1 to 100EO). Among them, lauryl alcohol 20EO, lauryl alcohol 30EO, decanol 3EO, decanol 5EO and oleyl alcohol 20EO may be mentioned more specifically.

[0101] Mixtures of these (poly)oxyethylated fatty alcohols can also be used.

[0102] Among nonionic surfactants, C6-C is preferred. 24 Alkyl polyglucosides and (poly)ethoxylated fatty alcohols, and more particularly using C8-C 16 Alkyl polyglucoside.

[0103] The amount of nonionic surfactant is preferably in the range of 0.5% to 20% by weight, particularly 1% to 10% by weight, and more particularly 2% to 5% by weight relative to the total weight of the composition of the invention.

[0104] According to another specific embodiment of the present invention, the composition comprises one or more anionic surfactants.

[0105] The term "anionic surfactant" refers to a surfactant that contains only anionic groups as ions or ionizable groups. These anionic groups are preferably selected from groups -C(O)OH, -C(O)O - -SO3H, -S(O)2O - -OS(O)2OH, -OS(O)2O - -P(O)2OH, -P(O)2O - -P(O)O2 - , -P(OH)2, =P(O)OH, -P(OH)O - =P(O)O - =POH and =PO - The anionic portion includes a cationic counterion, such as an alkali metal, alkaline earth metal, or ammonium; more preferably, the group is a carboxyl group -C(O)OH or a carboxyl group -C(O)O. - .

[0106] Examples of anionic surfactants that can be used in compositions according to the invention include alkyl carboxylic acids, alkyl sulfates, alkyl ether sulfates, alkyl amide ether sulfates, alkyl aryl polyether sulfates, glyceryl monoester sulfates, alkyl sulfonates, alkyl amide sulfonates, alkyl aryl sulfonates, α-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl amide sulfosuccinates, alkyl sulfoacetates, acyl sarcosinates, acyl glutamates, alkyl sulfosuccinates, acyl hydroxyethyl sulfonates and N-acyl taurates, salts of alkyl monoesters of polyglycoside-polycarboxylic acids, salts of alkyl diesters of polyglycoside-polycarboxylic acids, acyl lactylates, D-galactoside-uronic acid salts, alkyl ether carboxylates, alkyl aryl ether carboxylates, alkyl amino ether carboxylates; and the corresponding unsalted forms of all these compounds, wherein the alkyl and acyl groups comprise 8 to 30 carbon atoms and preferably 10 to 22 carbon atoms, and the aryl group represents phenyl.

[0107] These compounds can be oxyethylated and then preferably comprise 1 to 50 ethyleneoxy units.

[0108] C6-C of polyglycoside-polycarboxylic acid 24 Salts of alkyl monoesters can be selected from C6-C. 24 Alkyl polyglycoside-citrate, C6-C 24 Alkyl polyglycosides-tartrates and C6-C 24 Alkyl polyglycoside-sulfosuccinate.

[0109] When anionic surfactants are in salt form, they can be selected from alkali metal salts (such as sodium or potassium salts, and preferably sodium salts), ammonium salts, amine salts, especially amino alkoxides, or alkaline earth metal salts (such as magnesium salts).

[0110] Examples of amino alkoxides that may be mentioned in particular include monoethanolamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine and triisopropanolamine salts, 2-amino-2-methyl-1-propanol salts, 2-amino-2-methyl-1,3-propanediol salts, and tris(hydroxymethyl)aminomethane salts.

[0111] Alkali metal salts or alkaline earth metal salts are preferred, and sodium or magnesium salts are particularly preferred.

[0112] Among the anionic surfactants mentioned, C6-C is preferred. 24 )alkylcarboxylic acids, especially (C 10 -C 20 Alkyl carboxylic acids, preferably of natural origin, particularly of plant origin, such as stearic acid, which may be in the form of alkali metal salts, ammonium salts, amino alkoxides and alkaline earth metal salts; or mixtures of these compounds.

[0113] The amount of anionic surfactant is preferably in the range of 0.5% to 20% by weight, particularly 1% to 10% by weight, and more particularly 2% to 5% by weight relative to the total weight of the composition of the invention.

[0114] The amount of surfactant is preferably in the range of 0.5% to 30% by weight, particularly 1% to 20% by weight, more particularly 2% to 10% by weight, even more particularly 3% to 8% by weight, and more preferably 4% to 6% by weight relative to the total weight of the composition of the present invention.

[0115] iv) Organic thickening polymers:

[0116] According to a specific embodiment of the present invention, the composition comprises one or more thickening organic polymers.

[0117] The term "thickening polymer" refers to a polymer that, when introduced at 1% by weight into an aqueous solution or an aqueous-alcoholic solution containing 30% ethanol at pH 7, or into a mixture selected from liquid petrolatum, isopropyl myristate, or cyclopentadimethylsiloxane, enables the thickening polymer to be applied at 25°C and within 1 second. -1 A viscosity of at least 100 cps, and preferably at least 500 cps, is achieved at a shear rate of [missing information]. This viscosity can be measured using a cone / plate viscometer (Haake R600 rheometer, etc.). The thickening polymer can be a thickener for the aqueous phase and / or the aliphatic phase, preferably for the aqueous phase.

[0118] The term "organic" thickening polymer means a thickening polymer as defined above, which is formed of carbon and hydrogen, and possibly nitrogen, oxygen, sulfur, halogens (such as fluorine, chlorine or bromine), as well as phosphorus, alkali metals (such as sodium or potassium), or alkaline earth metals (such as magnesium or calcium). The organic polymers according to the invention do not contain any silicon.

[0119] The organic thickening polymer according to the present invention may be of natural or synthetic origin.

[0120] Thickening polymers can be associative or nonassociative anionic, cationic, amphoteric, or nonionic polymers, especially anionic polymers.

[0121] They can be thickeners used in the aqueous or oil phase.

[0122] As an aqueous thickening polymer, associative or non-associative thickening polymers, preferably non-associative thickening polymers containing sugar units, can be mentioned.

[0123] For the purposes of this invention, the term "sugar unit" refers to a unit derived from formula C. n (H2O) n-1 Or (CH2O) n The carbohydrate unit, which may optionally be modified by substitution and / or by oxidation and / or by dehydration.

[0124] The sugar units that may be included in the composition of the thickening polymer of the present invention are preferably derived from the following sugars: glucose, galactose, arabinose, rhamnose, mannose, xylose, fucose, dehydrated galactose, galacturonic acid, glucuronic acid, mannuronic acid, galactose sulfate, dehydrated galactose sulfate, and fructose.

[0125] In particular, the thickening polymers of the present invention include native gums, such as:

[0126] a) Exudates from trees or shrubs, including:

[0127] - Gum arabic (a branched polymer of galactose, arabinose, rhamnose and glucuronic acid);

[0128] -Solanum (a polymer derived from arabinose, galactose, mannose, xylose and glucuronic acid);

[0129] -Guardian pine resin (a polymer derived from galacturonic acid, galactose, rhamnose and glucuronic acid);

[0130] -Astragalus gum (a polymer of galacturonic acid, galactose, fucose, xylose and arabinose);

[0131] b) Gels derived from algae, including:

[0132] - Agar (a polymer derived from galactose and dehydrated galactose);

[0133] - Alginate (a polymer of mannulic acid and glucuronic acid);

[0134] - Carrageenan and red algae gum (polymers of galactosyl sulfate and dehydrated galactosyl sulfate);

[0135] c) Gum derived from seeds or tubers, including:

[0136] -Guar gum (a polymer of mannose and galactose);

[0137] - Locust bean gum (a polymer of mannose and galactose);

[0138] - Coumarin (a polymer of mannose and galactose);

[0139] Tamarind gum (a polymer of galactose, xylose, and glucose);

[0140] - Konjac gum (a polymer of glucose and mannose);

[0141] d) Microbial adhesives, including:

[0142] - Xanthan gum (a polymer of glucose, mannose acetate, mannose / pyruvate and glucuronic acid);

[0143] - Gellan gum (a polymer of partially acylated glucose, rhamnose, and glucuronic acid);

[0144] - Hard dextran gum (glucose polymer);

[0145] e) Plant extracts, including:

[0146] - Cellulose (glucose polymer);

[0147] - Starch (glucose polymer), and

[0148] -Inulin.

[0149] These polymers can be physically or chemically modified. Temperature is particularly important as a physical treatment.

[0150] As chemical treatments, esterification, etherification, amidation, or oxidation reactions can be mentioned. These treatments enable the production of polymers that can be nonionic, anionic, or amphoteric, in particular.

[0151] Preferably, these chemical or physical treatments are applied to guar gum, locust bean gum, starch, and cellulose.

[0152] The nonionic guar gum that can be used according to the present invention can be modified with C1-C6 (poly)hydroxyalkyl groups.

[0153] Among C1-C6 (poly)hydroxyalkyl groups, for example, hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl can be mentioned.

[0154] These guar gums are well known in the prior art and can be prepared, for example, by reacting a corresponding epoxide, such as propylene oxide, with guar gum to obtain guar gum modified with hydroxypropyl groups.

[0155] The degree of hydroxyalkylation is preferably in the range of 0.4 to 1.2 and corresponds to the number of epoxide molecules consumed by the number of free hydroxyl functional groups present on the guar gum.

[0156] Such nonionic guar gums, optionally modified with hydroxyalkyl groups, are sold by Rhodia Chimie under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120.

[0157] The plant source of the starch molecules used in this invention can be grains or tubers. Therefore, the starch is selected from, for example, corn starch, rice starch, cassava starch, barley starch, potato starch, wheat starch, sorghum starch, or pea starch.

[0158] Starch can be chemically or physically modified, particularly by one or more of the following reactions: pregelatinization, oxidation, crosslinking, esterification, etherification, amidation, or heat treatment.

[0159] Distarch phosphate or compounds rich in distarch phosphate are preferred, such as those sold by Avebe under the index numbers Prejel VA-70-T AGGL (gelled hydroxypropyl cassava distarch phosphate), or Prejel TK1 (gelled cassava distarch phosphate) or Prejel 200 (gelled acetyl cassava distarch phosphate), or Structure Zea (gelled corn distarch phosphate) from National Starch.

[0160] According to the present invention, amphoteric starches can also be used, which contain one or more anionic groups and one or more cationic groups. The anionic and cationic groups can bind to the same or different reaction sites of the starch molecule; they preferably bind to the same reaction site. The anionic group can be of the carboxyl, phosphate, or sulfate type, preferably of the carboxyl type. The cationic group can be of the primary, secondary, tertiary, or quaternary amine type.

[0161] Starch molecules can be derived from any plant source of starch, particularly from corn, potatoes, oats, rice, cassava, sorghum, barley, or wheat. Hydrolysates of the starches mentioned above can also be used. Starch is preferably derived from potatoes.

[0162] The non-associative thickening polymer of the present invention can be a cellulose-based polymer whose structure does not contain C. 10 -C 30 Fatty acid chains.

[0163] According to the present invention, the term "cellulose-based polymer" means any polysaccharide compound having in its structure a sequence of glucose residues linked together via β-1,4 bonds; cellulose derivatives, other than unsubstituted cellulose, can be anionic, cationic, amphoteric, or nonionic.

[0164] Therefore, the cellulose-based polymers of the present invention can be selected from unsubstituted cellulose, including those in microcrystalline form, and cellulose ethers.

[0165] Among these cellulose-based polymers, cellulose ethers, cellulose esters, and cellulose ether esters are distinguished.

[0166] Cellulose esters are inorganic esters of cellulose (nitrocellulose, cellulose sulfate, cellulose phosphate, etc.), organic cellulose esters (cellulose monoacetate, cellulose triacetate, cellulose amide propionate, cellulose acetate butyrate, cellulose acetate propionate, or cellulose acetate trimellitate, etc.), and mixed organic / inorganic esters of cellulose such as cellulose acetate butyrate sulfate and cellulose acetate propionate sulfate. Hydroxypropyl methyl phthalate and ethyl cellulose sulfate may be mentioned among cellulose ester ethers.

[0167] Without C 10 -C 30Nonionic cellulose ethers with aliphatic chains, i.e., "non-associative," may refer to (C1-C4)alkyl celluloses, such as methylcellulose and ethylcellulose (e.g., Ethocel Standard 100 Premium from Dow Chemical); (poly)hydroxy (C1-C4)alkyl celluloses, such as hydroxymethylcellulose, hydroxyethylcellulose (e.g., Natrosol 250HHR sold by Aqualon), and hydroxypropylcellulose (e.g., Klucel EF from Aqualon); mixed (poly)hydroxy (C1-C4)alkyl-(C1-C4)alkyl celluloses, such as hydroxypropyl methylcellulose (e.g., Methocel E4M from Dow Chemical), hydroxyethyl methylcellulose, hydroxyethyl ethylcellulose (e.g., Bermocoll E 481FQ from Akzo Nobel), and hydroxybutyl methylcellulose.

[0168] Among anionic cellulose ethers that do not have aliphatic chains, (poly)carboxyl (C1-C4) alkyl cellulose and its salts may be mentioned. Examples that may be mentioned include carboxymethyl cellulose, carboxymethyl methyl cellulose (e.g., Blanose 7M from Aqualon), and carboxymethyl hydroxyethyl cellulose and their sodium salts.

[0169] In cationic cellulose ethers that do not have aliphatic chains, references may be made to cationic cellulose derivatives, such as cellulose copolymers or cellulose derivatives grafted with water-soluble quaternary ammonium monomers, and are particularly described in patent US 4,131,576, such as (poly)hydroxy (C1-C4) alkyl celluloses, for example, hydroxymethyl cellulose, hydroxyethyl cellulose, or hydroxypropyl cellulose grafted particularly with methacryloyl ethyltrimethylammonium, methacrylamidopropyltrimethylammonium, or dimethyl diallyl ammonium salts. Commercial products corresponding to this definition are more specifically those from National Starch Company under the name... L 200 and Products sold by H 100.

[0170] According to a specific embodiment of the present invention, the thickening polymer of the present invention is composed of acrylate monomer CH2=C(R')-COOR”'(VIa) and / or acrylamide monomer CH2=C(R')-CO-N(R”)-LY - M +(VIb) is produced by the (co)polymerization of (VIa) and (VIb); in the formulas (VIa) and (VIb), R' and R” may be the same or different, representing a hydrogen atom or a (C1-C6) alkyl group such as methyl, preferably hydrogen, and R”' representing an alkali metal, alkaline earth metal, hydrogen atom or optionally, particularly substituted with one or more hydroxyl, carboxyl, or amino groups; preferably, R”' represents a hydrogen atom, and L represents a cyclic or acyclic, saturated or unsaturated, straight-chain or branched divalent hydrocarbon-based group, optionally inserted with one or more heteroatoms such as O or N and comprising 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms; preferably, L represents a divalent group -[C(R')(R”)] p -, where p represents an integer from 1 to 4, preferably 2 to 3 such as 2, and R' and R” are as defined above; more specifically, L represents -C(R')(R”)-CH2- or -CH2-C(R')(R”)-, where R' and R” are as defined above, and preferably R' and R” represent (C1-C4) alkyl such as methyl; Y - This indicates an anionic group, such as carboxylate, phosphate, phosphonate, sulfonate, or sulfate, preferably -S(O)2-O. - And M + The cation is a counterion, preferably an alkali metal such as sodium, and the copolymer may be in a direct emulsion or a reverse emulsion, preferably a reverse emulsion. More preferably, the thickening polymer of the present invention is composed of the acrylate monomer CH2=C(R')-COOH(VIa) as defined above and the acrylamide monomer CH2=C(R')-CO-N(R”)-LY. - M + The copolymerization of (VIb) is produced.

[0171] Among the non-associative thickening polymers that can be used without sugar units, crosslinked acrylic or methacrylic acid homopolymers or copolymers, crosslinked 2-acrylamido-2-methylpropanesulfonic acid homopolymers and their crosslinked or non-crosslinked acrylamide copolymers, ammonium acrylate homopolymers or copolymers of ammonium acrylate and acrylamide may be mentioned alone or as mixtures.

[0172] The first family of non-associative thickening polymers suitable for use are represented by cross-linked acrylic homopolymers.

[0173] Among this type of homopolymer, those crosslinked with sugar-based alkyl alcohol ethers can be mentioned, such as those sold by Noveon under the names Carbopol 980, 981, 954, 2984 and 5984, or by 3VSA under the names Synthalen M and Synthalen K.

[0174] Non-associated thickening polymers can also be cross-linked (meth)acrylic acid copolymers, such as the polymer marketed by Novotel under the name Aqua SF1.

[0175] Non-associative thickening polymers can be selected from cross-linked 2-acrylamido-2-methylpropanesulfonic acid homopolymers and their cross-linked acrylamide copolymers.

[0176] In the partially or completely neutralized crosslinked copolymers of 2-acrylamido-2-methylpropanesulfonic acid and acrylamide, the products described in Example 1 of EP 503 853 may be specifically mentioned, and reference may be made to the literature regarding these polymers.

[0177] The composition may similarly contain ammonium acrylate homopolymer or copolymer of ammonium acrylate and acrylamide as a non-associative thickening polymer.

[0178] Examples of ammonium acrylate homopolymers include those sold by Seppic Company under the name Simulgel 600 Acrylamide / Sodium Acryloyldimethyltaurate copolymer isohexadecane and polysorbate 80, and those sold by Hoechst under the name Microsap PAS 5193. Among copolymers of ammonium acrylate and acrylamide, those sold by Hoechst under the name Bozepol C Nouveau or PAS 5193 are also mentioned. For descriptions and preparations of such compounds, reference may be made in particular to FR 2 416 723, US 2 798 053, and US 2 923692.

[0179] Among aqueous thickening polymers, non-cellulose-based associative polymers that are well known to those skilled in the art and, in particular, have nonionic, anionic, cationic, or amphoteric properties may also be mentioned.

[0180] It should be understood that "associative polymers" are polymers that can reversibly associate with each other or with other molecules in an aqueous medium.

[0181] Their chemical structures are particularly characterized by containing at least one hydrophilic region and at least one hydrophobic region.

[0182] The term "hydrophobic group" means a group or polymer having a saturated or unsaturated, straight or branched hydrocarbon-based chain containing at least 10 carbon atoms, preferably 10 to 30 carbon atoms, particularly 12 to 30 carbon atoms, and more preferably 18 to 30 carbon atoms.

[0183] Preferably, the hydrocarbon-based group is derived from a monofunctional compound. By way of example, the hydrophobic group can be derived from fatty alcohols such as stearyl alcohol, dodecyl alcohol, or decanol. It can also represent hydrocarbon-based polymers, such as polybutadiene.

[0184] Among anionic associative polymers, the following can be mentioned:

[0185] -(a) Those comprising at least one hydrophilic unit and at least one aliphatic allyl ether unit, more particularly those whose hydrophilic unit is composed of an olefinic unsaturated anionic monomer, even more particularly vinyl carboxylic acid, and most particularly acrylic acid or methacrylic acid or mixtures thereof.

[0186] Among these anionic associative polymers, those particularly preferred according to the invention are polymers formed from 20% to 60% by weight of acrylic acid and / or methacrylic acid, 5% to 60% by weight of lower alkyl esters of (meth)acrylate, 2% to 50% by weight of aliphatic chain allyl ether, and 0% to 1% by weight of a crosslinking agent that is a well-known copolymerizable unsaturated polyene monomer, such as diallyl phthalate, allyl methacrylate, divinylbenzene, polyethylene glycol dimethacrylate, or methylenebisacrylamide.

[0187] Among the latter polymers, the most particularly preferred are cross-linked terpolymers of methacrylic acid, ethyl acrylate, and polyethylene glycol (10EO) stearyl alcohol ether (stearyl alcohol polyether-10), especially those produced by Ciba under the name Salcare SC. and Salcare SC Those sold are 30% aqueous emulsions of a crosslinked terpolymer of methacrylic acid, ethyl acrylate and stearyl alcohol polyether-10 allyl ether (40 / 50 / 10).

[0188] -(b) Contains i) at least one hydrophilic unit of the unsaturated olefinic carboxylic acid type and ii) at least one unsaturated carboxylic acid type (C 10 -C 30 Those alkyl esters with hydrophobic units.

[0189] The unsaturated carboxylic acid (C) useful in this invention 10 -C 30 Alkyl esters include, for example, lauryl acrylate, stearyl acrylate, decyl acrylate, isodecyl acrylate and dodecyl acrylate, and the corresponding methacrylates, lauryl methacrylate, stearyl methacrylate, decyl methacrylate, isodecyl methacrylate and dodecyl methacrylate.

[0190] For example, this type of anionic polymer is described and prepared according to patents US 3 915 921 and US 4 509 949.

[0191] In this type of anionic associative polymer, it is more particularly important to use acrylic acid (hydrophilic unit) composed of 95% to 60% by weight and acrylic acid C4% to 40% by weight. 10 -C 30 Those consisting of alkyl esters (hydrophobic units) and 0% to 6% by weight of crosslinked polymerizable monomers, or alternatively consisting of 98% to 96% by weight of acrylic acid (hydrophilic units) and 1% to 4% by weight of acrylic acid C 10 -C 30 Those consisting of alkyl esters (hydrophobic units) and 0.1% to 0.6% by weight of crosslinked polymerizable monomers, as previously described.

[0192] Of the polymers described above, the most particularly preferred according to the invention is that produced by Goodrich under the trade name Pemulen. Pemulen Carbopol And even better Pemulen Products sold, and products manufactured by Coatex Corporation under the name Coatex Products for sale.

[0193] You may also mention the acrylic / lauryl acrylate / vinylpyrrolidone terpolymer sold by ISP under the name Acrylidone LM;

[0194] -(c) maleic anhydride / C 30 -C 38 α-olefin / alkyl maleate terpolymer, such as that produced by Newphase Technologies under the name Performa V Products sold (maleic anhydride / C) 30 -C 38 α-olefin / isopropyl maleate copolymer);

[0195] -(d) Acrylic acid terpolymer, comprising:

[0196] i) Approximately 20% to 70% by weight of α,β-mono-olefinic unsaturated carboxylic acids [A],

[0197] ii) Approximately 20% to 80% by weight of α,β-monoolefinic unsaturated non-surfactant monomers other than [A],

[0198] iii) Approximately 0.5% to 60% by weight of nonionic monocarbamate, which is the product of the reaction between a monobasic surfactant and a monoolefinically unsaturated monoisocyanate.

[0199] The terpolymers described in patent application EP-A-0 173 109, and more particularly in Example 3, namely the terpolymer of methacrylate / methyl acrylate / benzyl isocyanate dimethyl-m-isopropenyl benzyl isocyanate ethoxylated (40EO), as an aqueous 25% dispersion;

[0200] -(e) copolymers, whose monomers include α,β-mono-unsaturated carboxylic acids and esters of α,β-mono-unsaturated carboxylic acids and oxyalkylene-modified fatty alcohols.

[0201] Preferably, these compounds also comprise esters of α,β-mono-olefinic unsaturated carboxylic acids and C1-C4 alcohols as monomers.

[0202] An example of this type of compound that can be mentioned is Aculyn 22, sold by Rohm & Haas, which is a terpolymer of methacrylate / ethyl acrylate / oxyolefinized stearate methacrylate;

[0203] -(f) Amphiphilic polymers comprising at least one olefinically unsaturated monomer with a sulfonic acid group in a partially or fully neutral form and comprising at least one hydrophobic moiety. These polymers may be crosslinked or non-crosslinked. They are preferably crosslinked.

[0204] Alkenyl unsaturated monomers with sulfonic acid groups are particularly selected from vinyl sulfonic acid, styrene sulfonic acid, and (meth)acrylamido (C1-C2) groups. 22 )alkyl sulfonic acid, N-(C1-C 22 )alkyl(meth)acrylamide group (C1-C 22 Alkyl sulfonic acids such as undecylacrylamidomethanesulfonic acid and their partially or completely neutralized forms.

[0205] More preferably, (meth)acrylamide (C1-C) groups are used. 22 Alkyl sulfonic acids, such as acrylamidomethanesulfonic acid, acrylamidoethanesulfonic acid, acrylamidopropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, methacrylamido-2-methylpropanesulfonic acid, 2-acrylamido-n-butanesulfonic acid, 2-acrylamido-2,4,4-trimethylpentanesulfonic acid, 2-methacrylamido-dodecyl sulfonic acid, or 2-acrylamido-2,6-dimethyl-3-heptanesulfonic acid, and their partially or completely neutralized forms.

[0206] It also uses 2-acrylamido-2-methylpropanesulfonic acid (AMPS) and its partially or completely neutralized form.

[0207] Polymers of this family, in particular, can be selected from those synthesized by interaction with C6-C. 22Random amphiphilic AMPS polymers modified by reaction of monoalkylamines or dialkylamines, and those as described in patent application WO 00 / 31154 (forming part of the description). These polymers may also contain other olefinically unsaturated hydrophilic monomers selected from, for example, (meth)acrylic acid, its β-substituted alkyl derivatives, or esters thereof obtained with monohydric alcohols or mono- or polyalkylene glycols, (meth)acrylamide, vinylpyrrolidone, maleic anhydride, itaconic acid, or maleic acid, or mixtures thereof.

[0208] Preferred polymers in this family are selected from amphiphilic copolymers of AMPS and at least one olefinically unsaturated hydrophobic monomer.

[0209] These same copolymers may also contain one or more olefinically unsaturated monomers that do not contain aliphatic chains, such as (meth)acrylic acid, its β-substituted alkyl derivatives or esters thereof obtained with monohydric alcohols or mono- or polyalkylene glycols, (meth)acrylamide, vinylpyrrolidone, maleic anhydride, itaconic acid or maleic acid or mixtures thereof.

[0210] These copolymers are particularly described in the following disclosures of patent application EP-A 750 899, patent US 5 089578, and Yotaro Morishima:

[0211] -Self-assembling amphiphilic polyelectrolytes and their nanostructures, Chinese Journal of Polymer Science, Vol. 18, No. 40, (2000), 323-336;

[0212] Micelle formation of random copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and a nonionic surfactant macromonomer in water asstudied by fluorescence and dynamic light scattering, Macromolecules, Vol. 33, No. 10, (2000), 3694-3704;

[0213] -Solution properties of micelle networks formed by nonionic moieties covalently bound to a polyelectrolyte: salt effects on rheological behavior - Langmuir, Vol. 16, No. 12, (2000), 5324-5332;

[0214] -Stimuli responsive amphiphilic copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and associative macromonomers, Polym. Preprint, Div. Polym. Chem., 40(2), (1999), 220-221.

[0215] Among these polymers, the following can be mentioned:

[0216] - Crosslinked or non-crosslinked, neutralized or unneutralized copolymers comprising 15% to 60% AMPS units and 40% to 85% (C8-C) polymers relative to the polymer. 16 )alkyl(meth)acrylamide or (meth)acrylic acid (C8-C 16 )alkyl ester units, such as those described in patent application EP-A750 899;

[0217] - A ternary polymer comprising 10 mol% to 90 mol% acrylamide units, 0.1 mol% to 10 mol% AMPS units, and 5 mol% to 80 mol% [unclear - possibly a specific component or component].

[0218] n-(C6-C 18 Alkyl acrylamide units, such as those described in patent US-5 089 578.

[0219] Also worth mentioning are fully neutralized copolymers of AMPS and dodecyl methacrylate, as well as crosslinked and non-crosslinked copolymers of AMPS and n-dodecylmethylacrylamide, as described in the Morishima article mentioned above.

[0220] Among cationic associative polymers, the following can be mentioned:

[0221] -(I) Cationic associative polyurethane;

[0222] -(II) A compound sold by Noveon under the name Aqua CC and corresponding to the INCI name polyacrylate-1 crosspolymer.

[0223] Polyacrylate-1 crosspolymer is the polymer product of a monomer mixture comprising:

[0224] *Di(C1-C4 alkyl)amino(C1-C6 alkyl) methacrylate,

[0225] *C1-C of one or more (meth)acrylic acids 30 Alkyl esters

[0226] *Polyethoxylated methacrylic acid C 10 -C 30 Alkyl esters (20-25 mol of ethylene oxide units),

[0227] *30 / 5 polyethylene glycol / polypropylene glycol allyl ether

[0228] *Hydroxy (C2-C6 alkyl) methacrylates, and

[0229] *Ethylene glycol dimethacrylate;

[0230] -(III) Quaternized (poly)hydroxyethyl cellulose modified with a group containing at least one aliphatic chain (such as an alkyl, aralkyl, or alkylaryl group or mixture thereof containing at least 8 carbon atoms). The alkyl group in the quaternized cellulose or hydroxyethyl cellulose preferably contains from 8 to 30 carbon atoms. The aryl group preferably represents phenyl, benzyl, naphthyl, or anthracene. (Note: C8-C...) 30 Examples of quaternized alkyl hydroxyethyl cellulose with fatty chains include Quatrisoft LM, a product marketed by Aqualon. Quatrisoft LM-X Quatrisoft LM-X (C 12 Alkyl) and Quatrisoft LM-X (C 18 Alkyl groups, and Crodacel, a product sold by Croda. Crodacel (C 12alkyl) and Crodacel (C 18 Alkyl groups and Softcat SL, a product sold by Ashland Corporation.

[0231] -(IV) cationic polyvinyl lactam polymer.

[0232] Such polymers are described, for example, in patent application WO-00 / 68282.

[0233] As the poly(vinyl lactam) polymer according to the present invention, vinylpyrrolidone / dimethylaminopropyl methacrylamide / dodecyl dimethylmethacrylamide propyl toluenesulfonate terpolymers, vinylpyrrolidone / dimethylaminopropyl methacrylamide / cocoyl dimethylmethacrylamide propyl toluenesulfonate terpolymers, vinylpyrrolidone / dimethylaminopropyl methacrylamide / lauryl dimethylmethacrylamide propyl toluenesulfonate or ammonium chloride terpolymers are particularly used.

[0234] The amphoteric associative polymers are preferably selected from those containing at least one non-cyclic cationic unit. Even more particularly, those prepared from or containing aliphatic chain monomers are preferred, preferably from 1 to 20 mol%, preferably 1.5 to 15 mol%, and even more particularly from 1.5 to 6 mol% of the total molar percentage of the monomers.

[0235] For example, the amphoteric associative polymer according to the present invention is described and prepared in patent application WO 98 / 44012.

[0236] Among the amphoteric associative polymers according to the invention, the preferred ones are acrylic acid / (meth)acrylamidopropyltrimethylammonium chloride / stearyl methacrylate terpolymers.

[0237] The nonionic associative polymers that can be used according to the present invention are preferably selected from:

[0238] (a) Copolymers of vinylpyrrolidone and aliphatic hydrophobic monomers, examples of which may be mentioned include:

[0239] - Antaron, a product sold by ISP companies or Ganex (Vinylpyrrolidone / hexadecene copolymer)

[0240] - Antaron, a product sold by ISP companies or Ganex (Vinylpyrrolidone / eicosene copolymer);

[0241] (b) A copolymer of methacrylic acid or alkyl acrylate (C1-C6) and an amphiphilic monomer containing at least one aliphatic chain, for example, by Goldschmidt under the name Antil. Oxyethylated methyl acrylate / stearyl acrylate copolymer for sale;

[0242] (c) A copolymer of a hydrophilic methacrylate or acrylate and a hydrophobic monomer containing at least one aliphatic chain, such as polyethylene glycol methacrylate / laurate methacrylate copolymer;

[0243] (d) A polyurethane polyether comprising, in its chain, both hydrophilic blocks (typically polyoxyethyleneized) and hydrophobic blocks (which may be separate aliphatic and / or alicyclic and / or aromatic sequences).

[0244] (e) Polymers having an amino-plastic ether backbone containing at least one aliphatic chain, such as Pure, sold by Sud-Chemie. Compounds;

[0245] (f) Cellulose or a derivative thereof, modified with a group comprising at least one aliphatic chain (such as alkyl, aralkyl, or alkylaryl, or mixtures thereof), wherein the alkyl group is C8, and in particular:

[0246] *Nonionic alkyl hydroxyethyl cellulose, such as Natrosol Plus Grade 330CS and Polysurf 67(C) sold by Ashland. 16 alkyl);

[0247] *Nonionic nonanoyl hydroxyethyl cellulose, such as Amercell HM-1500 sold by Amerchol;

[0248] *Nonionic alkyl cellulose, such as Bermocoll EHM 100 sold by Berrol Nobel;

[0249] (g) Associative guar gum derivatives, such as hydroxypropyl guar gum modified with aliphatic chains, such as Esaflor HM 22 (using C) sold by Lamberti. 22 Alkyl chain modification); Miracare XC 95-3 (using C) is a product sold by Rhodia Chimie. 14 Alkyl chain modification) and product RE 205-146 (using C 20 Alkyl chain modification).

[0250] Preferably, the polyurethane polyether comprises at least two lipophilic hydrocarbon-based chains, each containing 6 to 30 carbon atoms and separated by hydrophilic blocks. These hydrocarbon-based chains may be side chains or chains at the ends of the hydrophilic blocks. In particular, one or more side chains are contemplated. Furthermore, the polymer may include hydrocarbon-based chains at one or both ends of the hydrophilic blocks.

[0251] Polyurethane polyethers can be multiblock, particularly triblock. Hydrophobic blocks can be at each end of the chain (e.g., a triblock copolymer with a hydrophilic central block) or distributed at the ends and in the chain (e.g., a multiblock copolymer). These polymers can also be graft polymers or star polymers.

[0252] Aliphatic nonionic polyurethane polyethers can be triblock copolymers, where the hydrophilic blocks are polyoxyethyleneized chains containing 50 to 1000 oxyvinyl groups. Nonionic polyurethane polyethers contain urethane bonds between the hydrophilic blocks, hence the name.

[0253] As an extension, nonionic aliphatic chain polyurethane polyethers also include those in which the hydrophilic blocks are linked to the lipophilic blocks via other chemical bonds.

[0254] As an example of a nonionic aliphatic chain polyurethane polyether that can be used in this invention, Rheolate with urea functional groups, sold by Rheox, can also be used. or 208, 204, or 212, and also Acrysol RM

[0255] Also worth mentioning is the product from Akzo, which has a C... 12 -C 14 alkyl chain products Elfacos and with C 18 alkyl chain products Elfacos

[0256] Alternatively, products with C can be sold with a 20% solids content in water. 20 The alkyl chain and urethane bond are from Rohm and Haas's product DW.

[0257] Solutions or dispersions of these polymers can also be used, especially in water or in a water-alcohol medium. Examples of such polymers that may be mentioned include those marketed by Velos Corporation. 255. 278 and 244. Alternatively, products DW 1206F and DW 1206J sold by Rohm and Haas can be used.

[0258] The polyurethane polyethers that can be used according to the invention are particularly those described in the paper by G. Fonnum, J. Bakke and Fk. Hansen - Colloid Polym. Sci. [Colloid Polymer Science], 271, 380-389 (1993).

[0259] Even more particularly preferred is the use of polyurethane polyethers that can be obtained by polycondensation of at least three compounds, which include (i) at least one polyethylene glycol containing 150 to 180 mol of ethylene oxide, (ii) stearyl alcohol or decanol and (iii) at least one diisocyanate.

[0260] This type of polyurethane polyether is particularly known from Rohm and Haas under the name Aculyn and Aculyn Sales [Aculyn] It is a condensation polymer of polyethylene glycol, stearyl alcohol, and methylene bis(4-cyclohexyl isocyanate) (SMDI) containing 150 or 180 mol of ethylene oxides, at 15% by weight in a matrix of maltodextrin (4%) and water (81%); Aculyn It is a condensation polymer of polyethylene glycol, decanol and methylene bis(4-cyclohexyl isocyanate) (SMDI) containing 150 or 180 mol ethylene oxides, in a mixture of propylene glycol (39%) and water (26%) (35% by weight).

[0261] Fatty phase thickening polymers can also be used.

[0262] Preferably, the polymer used to construct the oil phase via physical interactions is selected from polyamides, polysiloxane polyamides, monoalkyl or polyalkyl esters of sugars or polysaccharides, N-acyl amino acid amide derivatives, and copolymers containing alkylene or styrene blocks. These copolymers may be diblock, triblock, multiblock, or radial block polymers, also known as star copolymers or alternatively comb polymers.

[0263] 1) Polymers containing at least one crystallizable block in the main chain

[0264] These are polymers that are soluble or dispersible in an oil or aliphatic phase by heating to above their melting point (mp). These polymers are particularly block copolymers composed of at least two blocks with different chemical properties, one of which is crystallizable.

[0265] As a polymer suitable for use in this invention, having at least one crystallizable block in the main chain, the following can be mentioned:

[0266] i) Polymers as defined in US-A-5 156 911;

[0267] ii) Block copolymers containing crystallizable olefins or cyclic olefins, such as those derived from the following block polymers:

[0268] - Cyclobutene, cyclohexene, cyclooctene, norbornene (i.e., dicyclo(2.2.1)hept-2-ene), 5-methylnorbornene, 5-ethylnorbornene, 5,6-dimethylnorbornene, 5,5,6-trimethylnorbornene, 5-ethylidenenorbornene, 5-phenylnorbornene

[0269] 5-Benzylnorbornene, 5-vinylnorbornene, 1,4,5,8-dimethylbridged-1,2,3,4,4a,5,8a-octahydronaphthalene, dicyclopentadiene, and mixtures thereof;

[0270] - With ethylene, propylene, 1-butene, 3-methyl-1-butene, 1-hexene, 4-methyl-1-pentene, 1-octene, 1-decene, or 1-eicosene, or mixtures thereof. These block copolymers can be, in particular, (ethylene / norbornene) block copolymers and (ethylene / propylene / ethylene norbornene) block terpolymers.

[0271] It can also be used with at least 2 C2-C 16 And even better C2-C 12 Those produced by block copolymerization of α-olefins, such as those mentioned above, and especially block copolymers of ethylene and 1-octene.

[0272] The copolymer contains at least one crystallizable block, and the remainder of the copolymer is amorphous (at room temperature). These copolymers may also contain two crystallizable blocks with different chemical properties. Preferred copolymers are those that simultaneously contain both crystallizable and amorphous blocks at room temperature, both of which are hydrophobic and lipophilic, and are sequentially distributed; examples of polymers containing, for instance, one of the following crystallizable blocks and one of the following amorphous blocks may be mentioned:

[0273] - Naturally crystallizable blocks: a) Polyester type, such as poly(alkylene terephthalate), b) Polyolefin type, such as polyethylene or polypropylene;

[0274] - Amorphous and lipophilic blocks, such as: amorphous polyolefins or copolymers (olefins), such as poly(isobutylene), hydrogenated polybutadiene, or hydrogenated poly(isoprene).

[0275] Examples of copolymers containing crystallizable and amorphous blocks include:

[0276] a) Poly(δ-caprolactone)-b-poly(butadiene) block copolymers, preferably used with hydrogenation, such as those described in S. Nojima, Macromolecules, 32, 3727-3734 (1999), in the article "Melting behavior of poly(δ-caprolactone)-block-polybutadiene copolymers".

[0277] b) Hydrogenated block or multiblock poly(butylene terephthalate)-b-poly(isoprene) block copolymers, which are mentioned in the paper "Study of morphological and mechanical properties of PP / PBT" by B. Boutevin et al., Polymer Bulletin, 34, 117-123 (1995).

[0278] c) Poly(ethylene)-b-copoly(ethylene / propylene) block copolymers, which are mentioned in P. Rangarajan et al.'s article "Morphology of semicrystalline block copolymers of ethylene(ethylene-alt-propylene)", Macromolecules, 26, 4640-4645 (1993) and P. Richter et al.'s article "Polymer aggregates with crystalline cores: the system poly(ethylene)poly(ethylene-propylene)", Macromolecules, 30, 1053-106825 (1997).

[0279] d) Poly(ethylene)-b-poly(ethylethylene) block copolymers, which are mentioned in IWHamley’s general article “Crystallization in block copolymers”, Advances in Polymer Science, Vol. 148, pp. 113-137 (1999).

[0280] The semi-crystalline polymers that can be used in the context of this invention can be non-crosslinked or partially crosslinked, provided that the degree of crosslinking does not prevent them from dissolving or dispersing in a liquid oil phase by heating above their melting point. It may then be a case of chemical crosslinking via reaction with a multifunctional monomer during polymerization. It may also be a case of physical crosslinking, which may then be due to the formation of hydrogen bonds or dipole-type bonds between groups on the polymer, such as dipole interactions between carboxylic acid ester ionomers, which are minor and carried by the polymer backbone; or due to phase separation between crystalline and amorphous blocks on the polymer.

[0281] Preferably, the semi-crystalline polymer suitable for use in this invention is non-crosslinked.

[0282] As a specific example of a semi-crystalline polymer that can be used in the compositions according to the invention, references can be made to the manual " The polymer described in the article comes from Landec. Products. These polymers are in solid form at room temperature (25°C). They have crystallizable side chains and contain monomers. Landec, with a melting point of 56°C, is particularly noteworthy. It is a sticky, impermeable, and non-sticky product at room temperature.

[0283] Alternatively, the semi-crystalline polymers described in Examples 3, 4, 5, 7, and 9 of patent US-A-5 156 911, which are composed of acrylic acid and (meth)acrylic acid C5 to C6, can be used. 16 The copolymerization of alkyl esters, such as those produced by the copolymerization of the following:

[0284] Acrylic acid, hexadecyl acrylate, and isodecyl acrylate in a 1 / 16 / 3 ratio.

[0285] Acrylic acid and pentadecanyl acrylate in a 1 / 19 ratio,

[0286] Acrylic acid, hexadecyl acrylate, and ethyl acrylate in a ratio of -2.5 / 76.5 / 20

[0287] Acrylic acid, hexadecyl acrylate, and methyl acrylate in a ratio of -5 / 85 / 10.

[0288] Acrylic acid and (meth)acrylate octadecyl ester in a ratio of -2.5 / 97.5.

[0289] Alternatively, polymer “Structure O” sold by National Starch Company, such as the product mp44°C described in US-A-5 736 125, and semi-crystalline polymers containing crystallizable side chains including fluorine groups, such as those described in Examples 1, 4, 6, 7 and 8 of WO-A-01 / 19333, may be used.

[0290] Semi-crystalline polymers obtained by copolymerization of stearate acrylate with acrylic acid or NVP, or by copolymerization of benzyl acrylate with acrylic acid or NVP, as described in US-A-5 519 063 or EP-A-0 550 745, may also be used.

[0291] According to specific embodiments and variations, semi-crystalline polymers, particularly alkyl acrylates, suitable for use in this invention may be mentioned, wherein Landec copolymers may be referenced:

[0292] -Doresco IPA Polyacrylic stearate, mp 49°C and MW 145,000;

[0293] -Doresco IPA Polyacrylate / methacrylic acid, mp = 65°C and MW = 114,000;

[0294] -Doresco IPA Polyacrylate / vinylpyrrolidone, mp is 44°C and MW is 387000;

[0295] -Doresco IPA Polyacrylate / hydroxyethyl methacrylate, mp is 47°C and MW is 397600;

[0296] -Doresco IPA Poly(succinate) acrylate, mp = 66℃.

[0297] 2) Non-polysiloxane polyamide

[0298] The specific polyamides used in the compositions according to the invention are preferably those described in UnionCamp's US-A-5 783 657.

[0299] The portion of US-A-5 783 657 concerning these polymers is incorporated by reference.

[0300] Each of these polyamides specifically conforms to the following formula (V):

[0301]

[0302] In equation (V):

[0303] -n indicates the total number of amide units, such that the number of ester groups accounts for 10% to 50% of the total number of ester and amide groups;

[0304] -R 1In each case, it is independently an alkyl or alkenyl group containing at least 4 carbon atoms, and especially 4 to 24 carbon atoms;

[0305] -R 2 In each case, C4 to C are represented independently. 55 Based on hydrocarbon groups, the condition is that at least 50% R 2 Group represents C 30 To C 55 Based on hydrocarbon groups;

[0306] -R 3 In each case, it independently represents an organic group having at least two carbon atoms, hydrogen atoms, and optionally one or more oxygen or nitrogen atoms; and

[0307] -R 4 In each case, hydrogen atoms, C1 to C1 are represented independently. 10 Alkyl or with R 3 Or with another R 4 The direct bonds of the bond make R 3 and R 4 The attached nitrogen atom is formed by R 4 -NR 3 Part of a defined heterocyclic structure, wherein at least 50% of R 4 The radical represents a hydrogen atom.

[0308] Specifically, the ester groups of this polyamide comprise 15% to 40% of the total number of ester and amide groups, and preferably 20% to 35%. Furthermore, n advantageously represents an integer ranging from 1 to 10, and even more preferably from 1 to 5, including end values.

[0309] Preferably, R 1 It is C 12 To C 22 And C is preferred 16 To C 22 Alkyl group. Advantageously, R 2 It can be C 10 To C 42 Based on hydrocarbon (alkylene) groups. Preferably, at least 50% and even more preferably at least 75% of R 2 The group is a group containing 30 to 42 carbon atoms. Other R 2 It is hydrogenated C4 to C 19 And C4 to C are preferred. 12 Group. Preferably, R 3 Indicates C2 to C 36 Based on hydrocarbon groups or polyoxyalkylene groups, and R 4 Represents a hydrogen atom. Preferably, R 3 Indicates C2 to C 12Hydrocarbon-based groups. Hydrocarbon-based groups can be straight-chain, cyclic, or branched, and can be saturated or unsaturated. Furthermore, alkyl and alkylene groups can be straight-chain or branched, and can be saturated or unsaturated.

[0310] Thickening of the oil phase can be achieved using one or more polyamides as defined above. Typically, these polyamides are in the form of mixtures, which may also contain synthetic products corresponding to the polyamides as defined above, where n is 0, i.e., diesters.

[0311] As a structured polyamide that can be used in this invention, reference can also be made to polyamide resins produced by the condensation of aliphatic dicarboxylic acids and diamines (including compounds containing more than two carboxyl groups and more than two amine groups, respectively), wherein the carboxyl and amine groups of adjacent individual units are condensed in the form of amide bonds. These polyamide resins are particularly those produced by General Mills, Inc. under the trade name Versamid and by Henkel Corp. under the trade name... Especially Products sold under S or C. These resins have a weight-average molecular weight ranging from 6,000 to 9,000. Further information regarding these polyamides can be found in US-A-3 645 705 and US-A-3 148 125. Especially for... 30 or 744.

[0312] Polyamides sold or manufactured by Arizona Corporation under index numbers Uni-Rez (2658, 2931, 2970, 2621, 2613, 2624, 2665, 1554, 2623, 2662) and by Henkel Corporation under index number Macromelt 6212 may also be used. Further information regarding these polyamides can be found in US-A-5 500 209.

[0313] As examples of structured polyamides that can be used in compositions according to the invention, references can also be made to commercial products sold or manufactured by Arizona Chemical Company under the names Uniclear 80 and Uniclear 100. These are sold as 80% (active material) gel and 100% (active material) gel in mineral oil, respectively. They have softening points of 88°C to 105°C. These commercial products are mixtures of copolymers of C36 diacid bound to ethylenediamine, having an average molecular weight of about 6000. Ester-terminal groups are generated by esterification of the remaining acidic end groups with cetyl alcohol, stearyl alcohol, or mixtures thereof (also known as cetearyl alcohol).

[0314] 2) Monoalkyl or polyalkyl esters of sugars or polysaccharides

[0315] Among the sugars or polysaccharides suitable for use in this invention, dextrin or inulin alkyl or polyalkyl esters may be mentioned.

[0316] It can be, in particular, a dextrin monoester or polyester of at least one fatty acid (especially corresponding to formula (VI)):

[0317]

[0318] In equation (VI):

[0319] -n is an integer in the range of 3 to 200, especially in the range of 20 to 150, and particularly in the range of 25 to 50.

[0320] -R1, R2 and R3, which may be the same or different, are selected from hydrogen and acyl (RC(O)-), wherein the group R is a straight or branched, saturated or unsaturated hydrocarbon-based group containing 7 to 29, particularly 7 to 21, especially 11 to 19, more particularly 13 to 17 or even 15 carbon atoms, provided that at least one of said groups R1, R2 or R3 is not hydrogen.

[0321] Specifically, R1, R2, and R3 may represent hydrogen or acyl (RC(O)-), where R is a hydrocarbon-based group as defined above, provided that at least two of the groups R1, R2, or R3 are identical and not hydrogen.

[0322] Groups R1, R2, and R3 may all contain acyl groups (RC(O)-), which may be the same or different, and especially the same.

[0323] Specifically, in the general formula of sugar esters that can be used in this invention, the previously mentioned range of n is advantageously 25 to 50 and in particular equal to 38.

[0324] Especially when groups R1, R2, and / or R3 (the same or different) contain acyl groups (RC(O)), these groups can be selected from octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, benzyl acid, isobutyric acid, isovaleric acid, 2-ethylbutyric acid, ethylmethylacetic acid, isoheptanoic acid, 2-ethylhexanoic acid, isononanoic acid, isodecanonic acid, isotriadecanoic ... Fatty acid group, isoarachidic acid group, isohexanoic acid group, decenoic acid group, dodecenoic acid group, tetradecenoic acid group, myristonenic acid group, hexadecenoic acid group, palmitoleic acid group, oleic acid group, transoleic acid group, asclepinic acid group, gondoleic acid group, eicosenoic acid group, sorbic acid group, linoleic acid group, linolenic acid group, punicic acid group, octadecanoic acid group, arachidonic acid group and stearyl alkynyl group, and mixtures thereof.

[0325] Preferably, at least one dextrin palmitate is used as a fatty acid ester of dextrin. This ester can be used alone or as a mixture with other esters.

[0326] Advantageously, the fatty acid esters of dextrin have a degree of substitution of less than or equal to 2.5 based on a glucose unit, particularly in the range of 1.5 to 2.5 and preferably 2 to 2.5. The weight-average molecular weight of the dextrin ester can be particularly 10,000 to 150,000, particularly 12,000 to 100,000 and even 15,000 to 80,000.

[0327] Dextrin esters, especially dextrin palmitate, are commercially available from Chiba Flour under the names Rheopearl TL or Rheopearl KL.

[0328] 3) N-acyl amino acid amide derivatives

[0329] The N-acyl amino acid amides that can be used are, for example, diamides derived from combinations of N-acyl amino acids and amines containing 1 to 22 carbon atoms, such as those described in FR 2 281 162. These are, for example, alkyl glutamate amide derivatives, such as lauryl glutamate dibutylamide sold by Ajinomoto under the name Gelling Agent GP-1, or alternatively, 2-ethylhexyl glutamate dibutylamide sold by Ajinomoto under the name Gelling Agent GA-01.

[0330] 4) Copolymers containing olefin or styrene blocks

[0331] The copolymer may have a comb-like structure or a diblock, triblock, multiblock, and / or radial or star-shaped block structure, and may contain at least two thermodynamically incompatible segments.

[0332] The structuring agent may contain, for example, styrene segment blocks as described in patent applications EP 0 497 144, WO 98 / 42298, US 6 225 690, US 6 174 968 and US 6 225 390, ethylene / butene or ethylene / propylene segments as described in patent applications US 6 225 690, US 6174 968 and US 6 225 390, butadiene segments, isoprene segments, polyvinyl segments, such as poly(meth)acrylate or polyvinyl alcohol or polyvinyl acetate, silicone segments as described in patent applications US 5 468 477 and US 5 725 882, or combinations of these segments.

[0333] Diblock copolymers are typically defined as type AB, where a hard segment (A) is followed by a soft segment (B).

[0334] Triblock copolymers are typically defined as ABA-type copolymers or copolymers with a ratio of hard segments, soft segments, and hard segments.

[0335] Multiblock, radial, or star copolymers can contain any combination of hard and soft segments, provided that the properties of the hard and soft segments are preserved.

[0336] Examples of hard segments of block copolymers that may be mentioned are styrene, and examples of soft segments of block copolymers that may be mentioned include ethylene, propylene, and butene, and combinations thereof.

[0337] Triblock copolymers suitable for use in this invention, and especially those of the polystyrene / polyisoprene or polystyrene / polybutadiene type, may be those sold by BASF under index number Luvitol HSB. Also mentioned are triblock copolymers of the polystyrene / copolymer (ethylene-propylene) or polystyrene / copolymer (ethylene-butene) type, such as those sold by Shell Chemical Co. under index number Kraton or by Penreco under index number GelledPermethyl 99A. Such triblock copolymers are particularly preferred according to the invention.

[0338] As further examples of block copolymers applicable to the present invention, references may also be made to those block copolymers sold by Penreco under the index number Versagel, those sold by Shell under the index number Kraton, and those sold by Brooks Industries under the index number Gel Base.

[0339] In aliphatic phase thickening polymers, polymers with at least one crystallizable block in the main chain are preferred.

[0340] Aqueous or fatty phase thickening polymers can be used alone or as a mixture in all proportions.

[0341] Preferably, the thickener is an aqueous thickener.

[0342] Preferably, the polymer in the cosmetic composition according to the invention is advantageously present in water at 1% of the active material in solution or in dispersion for 200 seconds. -1 It has a viscosity greater than 0.1 ps and even more advantageously greater than 0.2 cp at a shear rate, as measured using a Rheomat RM 180 rheometer at 25 °C.

[0343] According to a preferred embodiment of the present invention, the thickening polymer of the present invention is non-associative and preferably composed of acrylate monomer CH2=C(R')-COOR”'(VIa) and / or acrylamide monomer CH2=C(R')-CO-N(R”)-LY - M + (VIb) is produced by the (co)polymerization of (VIa) and (VIb); in the formulas (VIa) and (VIb), R' and R” may be the same or different, representing a hydrogen atom or a (C1-C6) alkyl group such as methyl, preferably hydrogen, R”' representing an alkali metal, alkaline earth metal, hydrogen atom or optionally, particularly substituted with one or more hydroxyl, carboxyl or amino groups, and L representing a cyclic or acyclic, saturated or unsaturated, straight or branched divalent hydrocarbon-based group optionally inserted or substituted with one or more heteroatoms such as O or N and containing 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms; preferably, L represents a divalent group - [C(R')(R”)] p - where p represents an integer from 1 to 4, preferably 2 to 3, such as 2, and R' and R” are as defined above; more specifically, L represents -C(R')(R”)-CH2- or -CH2-C(R')(R”)-, where R' and R” are as defined above; preferably, R' and R” represent (1-C4)alkyl such as methyl; Y- represents an anionic group, such as carboxylate, phosphate, phosphonate, sulfonate or sulfate, preferably -S(O)2-O - And M + The cation is a counterion, preferably an alkali metal such as sodium, and the copolymer may be in a direct emulsion or a reverse emulsion, preferably a reverse emulsion. More preferably, the thickening polymer of the present invention is composed of the acrylate monomer CH2=C(R')-COOH(VIa) as defined above and the acrylamide monomer CH2=C(R')-CO-N(R”)-LY. - M + (VIb) is produced by copolymerization. Among the thickening polymers, the following may be mentioned: preferably, the organic thickening polymer is selected from crosslinked or non-crosslinked acrylic copolymers or methacrylic copolymers, either alone or as a mixture, crosslinked or non-crosslinked 2-acrylamido-2-methylpropanesulfonic acid homopolymers and their crosslinked or non-crosslinked acrylamide copolymers, ammonium acrylate homopolymers or copolymers of ammonium acrylate and acrylamide.

[0344] According to advantageous variants, the compositions of the present invention comprise one or more associated or non-associated thickening polymers, preferably non-associated, comprising sugar units particularly derived from the following sugars: glucose; galactose; arabinose; rhamnose; mannose; xylose; fucose; dehydrated galactose; galacturonic acid; glucuronic acid; mannuronic acid; galactose sulfate; dehydrated galactose sulfate and fructose, preferably dehydrated galactose, preferably agar.

[0345] Preferably, the organic thickening polymer is present in the composition according to the invention in an amount ranging from 0.01% to 10% by weight, and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

[0346] According to specific embodiments, the weight ratio of fatty substances to surfactants is 5 to 20, preferably 8 to 15, and even more preferably 10 to 13, such as 11.8.

[0347] According to one embodiment of the invention, the weight ratio of the fatty substance / surfactant and polymer [surfactant + polymer] is from 0.8 to 10, particularly from 1 to 5, more particularly from 1.5 to 2.5, such as 1.8 or 1.9, preferably 1.9.

[0348] v) Fatty substances

[0349] According to specific embodiments of the present invention, the composition of the present invention further comprises v) one or more fatty substances. In particular, the fatty substances of the present invention are not oxyalkylated.

[0350] Preferably, the fatty substances of the present invention are selected from hydrocarbons, fatty alcohols, fatty esters, silicones, and fatty ethers, or mixtures thereof.

[0351] The fatty substance of the present invention is resistant to oxidation at room temperature (25°C) and atmospheric pressure (760 mmHg; i.e., 1.013 × 10⁻⁶). 5 The substance under (Pa) can be either liquid or non-liquid.

[0352] The liquid fatty substance of the present invention preferably has a viscosity of less than or equal to 2 Pa·s at a temperature of 25°C and a shear rate of 1 s⁻¹, more preferably less than or equal to 1 Pa·s, and even more preferably less than or equal to 0.1 Pa·s.

[0353] The term "liquid hydrocarbon" refers to hydrocarbons composed solely of carbon and hydrogen atoms, which, at room temperature (25°C) and atmospheric pressure (760 mmHg; i.e., 1.013 × 10⁻⁶), are soluble in carbon and hydrogen atoms. 5 The liquid is below (Pa).

[0354] More specifically, the liquid hydrocarbons are selected from:

[0355] - Straight-chain or branched, optionally cyclic C6-C 16 Alkanes. Examples that may be mentioned include hexane, undecane, dodecane, tridecane, and isoalkanes such as isohexadecane, isododecane, and isodecane;

[0356] - Inorganic, animal, or synthetic straight-chain or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffin, liquid petrolatum, polydecene, hydrogenated polyisobutylene, etc. And squalane.

[0357] In preferred variants, the liquid hydrocarbon is selected from liquid paraffin and liquid petrolatum.

[0358] The term "liquid fatty alcohol" refers to non-glycerolized and non-oxyenized fatty alcohols, which, at standard temperature (25°C) and atmospheric pressure (760 mmHg; i.e., 1.013 × 10⁻⁶), are suitable for liquid fatty alcohols. 5 The liquid is below (Pa).

[0359] Preferably, the liquid fatty alcohol of the present invention contains 8 to 30 carbon atoms, more preferably C. 10 -C 22 , or even better C 14 -C 20 Even better C 16 -C 18 .

[0360] The liquid fatty alcohol of the present invention can be saturated or unsaturated.

[0361] Saturated liquid fatty alcohols are preferably branched. They may optionally contain at least one aromatic or non-aromatic ring in their structure. Preferably, they are acyclic.

[0362] More specifically, the liquid saturated fatty alcohol of the present invention is selected from octyldodecyl alcohol, isostearyl alcohol, or 2-hexyldecyl alcohol.

[0363] According to another variant of the invention, the fatty substance is selected from liquid unsaturated fatty alcohols. These unsaturated liquid fatty alcohols contain at least one double or triple bond in their structure. Preferably, the fatty alcohols of the invention have one or more double bonds in their structure. When several double bonds are present, two or three double bonds are preferably present, and they can be conjugated or non-conjugated.

[0364] These unsaturated fatty alcohols can be straight-chain or branched.

[0365] They may optionally contain at least one aromatic or non-aromatic ring in their structure. Preferably, they are acyclic.

[0366] More specifically, the unsaturated liquid fatty alcohol of the present invention is selected from oleyl alcohol, linoleyl alcohol, linolenic acid alcohol and undecenoyl alcohol.

[0367] Oleol is the most preferred choice.

[0368] The term "liquid fatty ester" refers to esters derived from fatty acids and / or fatty alcohols, and which are soluble in water at room temperature (25°C) and atmospheric pressure (760 mmHg; i.e., 1.013 × 10⁻⁶). 5 The liquid is below (Pa).

[0369] The ester is preferably saturated or unsaturated, and straight-chain or branched C1-C. 26 Aliphatic monocarboxylic or polycarboxylic acids and saturated or unsaturated, straight-chain or branched C1-C 26 Liquid esters of aliphatic monohydric or polyhydric alcohols, wherein the total number of carbon atoms in these esters is greater than or equal to 10.

[0370] Preferably, for the esters of monohydric alcohols, at least one of the alcohols and acids from which the esters of the present invention are derived is branched.

[0371] Among the monoesters of monobasic acids and monohydric alcohols, ethyl palmitate, isopropyl palmitate, alkyl myristate esters such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isodecanyl neopentanoate, isostearyl neopentanoate, and C 10 -C 22 And preferably C 12 -C 20 Alkyl (iso)stearates, such as isopropyl isostearate.

[0372] You can also use C4-C 22 Dicarboxylic or tricarboxylic acids and C1-C 22 Esters of alcohols, as well as monocarboxylic acids, dicarboxylic acids, or tricarboxylic acids, and non-sugar dihydroxy, trihydroxy, tetrahydroxy, or pentahydroxy C4-C. 26 Esters of alcohols.

[0373] Specifically mentioned are: diethyl sebacate, diisopropyl sebacate, di(2-ethylhexyl) sebacate, diisopropyl adipate, di-n-propyl adipate, dioctyl adipate, bis(2-ethylhexyl) adipate, diisostearate adipate, bis(2-ethylhexyl) maleate, triisopropyl citrate, triisoceryl citrate, triisostearate citrate, trilactyl glycerol, trioctyl dodecyl citrate, trioleate citrate, neopentyl glycol diheptanoate, and diethylene glycol diisononanoate.

[0374] The composition may also contain C6-C 30 Preferably C 12 -C 22 Glycoesters and diesters of fatty acids are liquid fatty esters. It should be noted that the term "sugar" refers to an oxygen-based hydrocarbon compound containing several alcohol functional groups, with or without aldehyde or ketone functional groups, and comprising at least four carbon atoms. These sugars can be monosaccharides, oligosaccharides, or polysaccharides.

[0375] Suitable examples of sugars that may be mentioned include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, and lactose, as well as their derivatives, especially alkyl derivatives such as methyl derivatives, for example, methyl glucose.

[0376] The glycol esters of fatty acids may be selected, in particular, from the group consisting of: the previously described sugars and straight-chain or branched, saturated or unsaturated C6-C fatty acids. 30 And C is preferred 12 -C 22 Esters or mixtures of fatty acids. If they are unsaturated, these compounds may contain one to three conjugated or non-conjugated carbon-carbon double bonds.

[0377] The esters according to this variant can also be selected from monoesters, diesters, triesters and tetraesters, polyesters and mixtures thereof.

[0378] These esters can be, for example, oleate, laurate, palmitate, myristate, behenate, cocoate, stearate, linoleate, linolenic acid ester, decanoate, and arachidonic acid esters or mixtures thereof, such as, in particular, mixed esters of oleopalatate, oleostearate, and palmitoylstearate.

[0379] More specifically, monoesters and diesters are used, and especially monooleate or dioleate, stearate, benzyl ester, oleopalatate, linoleate, linolenic acid ester or oleostearate of sucrose, glucose or methyl glucose.

[0380] One example that can be mentioned is Amerchol, which uses the name... The product sold by DO is methyl gluconate dioleate.

[0381] Finally, natural or synthetic glycerides of mono-, di-, or tri-acids can also be used.

[0382] Among these, vegetable oils can be mentioned.

[0383] Examples of oils that can be used as plant-based or synthetic triglycerides in the compositions of the present invention include:

[0384] - Triglyceride oils of plant or synthetic origin, such as liquid fatty acid triglycerides comprising 6 to 30 carbon atoms, such as heptanoic acid or caprylic acid triglycerides, or alternatively, such as sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, almond oil, macadamia nut oil, aurora oil, castor oil, avocado oil; caprylic / capric acid triglycerides, such as those sold by Stéarinerie Dubois or by Dynamit Nobel under the name... Those sold in 810, 812, and 818 are jojoba oil and shea butter;

[0385] Preferably, the liquid fatty ester produced from a monohydric alcohol will be used as the ester according to the invention.

[0386] Isopropyl myristate or isopropyl palmitate are preferred.

[0387] The term "liquid silicone" refers to silicone that is produced at room temperature (25°C) and atmospheric pressure (760 mmHg; i.e., 1.013 × 10⁻⁶). 5 The liquid is below (Pa).

[0388] Preferably, the silicone is selected from liquid polydialkylsiloxanes, especially liquid polydimethylsiloxane (PDMS), and liquid polyorganosiloxanes containing at least one aryl group.

[0389] These silicones can also be organically modified. Organically modified silicones that can be used according to the present invention are liquid silicones as previously defined and whose structure contains one or more organic functional groups attached via hydrocarbon-based groups.

[0390] Organopolysiloxanes are defined in more detail in Walter Noll's *Chemistry and Technology of Silicones* (1968), Academic Press. They can be volatile or non-volatile.

[0391] When they are volatile, these silicones are more specifically selected from those having a boiling point between 60°C and 260°C, and even more specifically selected from:

[0392] (i) Cyclic polydialkylsiloxanes containing 3 to 7, preferably 4 to 5, silicon atoms. These are, for example, produced by Union Carbide under the name Volatile. 7207 or by Rhodia under the name The octamethylcyclotetrasiloxane sold by 70045V2 was manufactured by Union Carbide under the name Silicone. 7158. By Rhodia Company under the name The decamethylcyclopentane sold by 70045V5, and dodecylcyclopentane, or cyclohexadimethylsiloxane, and mixtures thereof sold by Momentive Performance Materials under the name Silsoft 1217.

[0393] Also mentioned are dimethylsiloxane / methylalkylsiloxane type cyclized copolymers, such as the silicone with the following formula sold by Union Carbide Corporation. FZ 3109:

[0394]

[0395] Mixtures of cyclic polydialkylsiloxanes with organosilicon compounds may also be mentioned, such as a mixture of octamethylcyclotetrasiloxane and tetratrimethylsilyl pentaerythritol (50 / 50) and a mixture of octamethylcyclotetrasiloxane and oxy-1,1'-bis(2,2,2',2',3,3'-hexatrimethylsilyloxy)neopentane;

[0396] (ii) Contains 2 to 9 silicon atoms and has a silicon content of less than or equal to 5 × 10⁻⁶ at 25 °C. -6 m 2 Linear volatile polydialkylsiloxanes with a viscosity of / s. An example is, in particular, decamethyltetrasiloxane, marketed by Toray Silicone under the name SH 200. Silicones belonging to this class are also described in Todd & Byers' article "Volatile Silicone Fluids for Cosmetics," published in Cosmetics and Toiletries, Vol. 91, January 1976, pp. 27-32. The viscosity of these silicones was measured at 25°C according to Appendix C of ASTM 445.

[0397] Non-volatile polydialkylsiloxanes can also be used.

[0398] These non-volatile silicones are more specifically selected from polydialkylsiloxanes, among which polydimethylsiloxanes with trimethylsilyl end groups are particularly noteworthy.

[0399] Among these polydialkylsiloxanes, the following commercial products may be mentioned in a non-restrictive manner:

[0400] - The 47 and 70 047 series sold by Rhodia oil or Oil, for example, oil 70047V 500 000;

[0401] - Sold by Rhodia Series of oils;

[0402] - Oils from Dow Corning's 200 series, such as those with a 60,000mm... 2 The viscosity of DC200 / s;

[0403] -From General Electric Oils, as well as certain oils from General Electric's SF series (SF 96, SF 18).

[0404] Also mentioned are polydimethylsiloxanes with dimethylsilanol end groups known by the name polydimethylsiloxane alcohol (CTFA), such as oils from Rhodia's 48 series.

[0405] Among aryl-containing silicones are polydiarylsiloxanes, particularly polydiphenylsiloxanes and polyalkylarylsiloxanes. Examples that may be mentioned include products sold under the following names:

[0406] - From Rhodia's 70 641 series Oil;

[0407] -From Rhodia Oils in the 70, 633, and 763 series;

[0408] - Oil from Dow Corning 556, a cosmetic grade fluid;

[0409] - Silicones from Bayer's PK series, such as product PK20;

[0410] - Certain oils from General Electric's SF series, such as SF 1023, SF 1154, SF 1250 and SF 1265.

[0411] Organically modified liquid silicones may contain, in particular, polyethylidene and / or polypropylene oxides. Therefore, examples include silicone KF-6017 sold by Shin-Etsu Corporation, and oils from Union Carbide Corporation. L722 and L77.

[0412] Liquid fatty ethers are selected from liquid dialkyl ethers, such as dioctyl ether.

[0413] Fatty substances can be non-liquid at room temperature and atmospheric pressure.

[0414] The term "non-liquid" preferably means a solid compound or a compound that is heated to 25°C and reacts within 1 second. -1 Compounds that have a viscosity greater than 2 Pa·s at a certain shear rate.

[0415] More specifically, the non-liquid fatty substance is selected from fatty alcohols, fatty acids and / or fatty alcohol esters, non-silicone waxes, silicones or fatty ethers, which are non-liquid and preferably solid.

[0416] The non-liquid fatty alcohols suitable for use in this invention are more particularly selected from saturated or unsaturated, straight-chain or branched alcohols comprising 8 to 30 carbon atoms, and these alcohols are more preferably C10-3 ... 10 -C 22 , or even better C 14 -C 20 Even better C 16 -C 18 .

[0417] Cetyl alcohol and stearyl alcohol, and mixtures thereof (cetearyl alcohol) are the most particularly preferred.

[0418] Regarding esters of non-liquid fatty acids and / or fatty alcohols, those derived from C9-C may be mentioned in particular. 26 Fatty acids and C9-C 26 Solid esters of fatty alcohols.

[0419] Among these esters, octyl dodecyl behenate, isocetyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate, decyl oleate, myristyl stearate, octyl palmitate, octyl nonanoate, octyl stearate, alkyl myristate esters such as cetyl myristate, myristate myristate, or stearyl myristate; hexyl stearate, and more particularly myristate myristate.

[0420] Still within the context of this variant, C4-C can also be used. 22 Dicarboxylic or tricarboxylic acids and C1-C 22 Esters of alcohols, as well as monocarboxylic acids, dicarboxylic acids, or tricarboxylic acids and C2-C 26 Esters of dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols.

[0421] In particular, the following can be mentioned: diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; and dioctyl maleate.

[0422] Of all the additional esters mentioned above, myristyl palmitate, cetyl palmitate, or stearyl palmitate, alkyl myristate esters such as cetyl myristate and stearyl myristate are preferred.

[0423] (Non-silicone) waxes, especially those selected from carnauba wax, candelilla wax, Spanish grass wax, paraffin wax, ceresin wax, plant waxes such as olive tree wax, rice wax, hydrogenated jojoba wax, or flowerabsolute wax, such as blackcurrantblossom essential wax sold by Bertin (France), or animal waxes such as beeswax or modified beeswax (cerabellina); white beeswax, such as those sold by Koster Keunen; generally, other waxes or wax raw materials that can be used according to the invention, especially marine waxes, such as products sold by Sophim under index number M82, polyethylene waxes, or polyolefin waxes.

[0424] The non-liquid silicone according to the present invention may be in the form of wax, resin or glue.

[0425] Preferably, the non-liquid silicone is selected from polydialkylsiloxanes, especially polydimethylsiloxane (PDMS), and organically modified polysiloxanes comprising at least one functional group selected from poly(alkylene oxide), amino, and alkoxy groups.

[0426] The silicone sealant that can be used according to the invention, especially polydialkylsiloxanes and preferably polydimethylsiloxanes with a high number average molecular weight of 200,000 to 1,000,000, can be used alone or in mixtures in a solvent. This solvent can be selected from volatile silicones, polydimethylsiloxane (PDMS) oil, polyphenylmethylsiloxane (PPMS) oil, isoparaffins, polyisobutylene, dichloromethane, pentane, dodecane, and tridecane, or mixtures thereof.

[0427] More specifically, the products that can be used according to the present invention are mixtures, such as:

[0428] - A mixture of polydimethylsiloxane or polydimethylsiloxane alcohol (CTFA) with hydroxyl-terminated chains and cyclic polydimethylsiloxane (CTFA), such as product Q21401 sold by Dow Corning.

[0429] - A mixture of polydimethylsiloxane adhesive and cyclic silicone, such as SF 1214 silicone fluid from General Electric Company; this product is SF 30 adhesive corresponding to polydimethylsiloxane with a number average molecular weight of 500,000, soluble in SF 1202 silicone fluid corresponding to decamethylcyclopentane.

[0430] - A mixture of two PDMS with different viscosities, and more specifically, a mixture of PDMS adhesive and PDMS oil, such as product SF 1236 from General Electric. Product SF 1236 is as defined above, with a viscosity of 20m... 2 SE 30 adhesive with a viscosity of / s and 5×10 6 m 2 This product is a mixture of SF 96 oil with a viscosity of / s. It preferably comprises 15% SE30 adhesive and 85% SF 96 oil.

[0431] The organopolysiloxane resin that can be used according to the present invention is a crosslinked siloxane system comprising the following units:

[0432] R2SiO 2 / 2 R3SiO 1 / 2 ,RSiO 3 / 2 and SiO 4 / 2 ,

[0433] In these formulas:

[0434] R can be the same or different, preferably the same, and represents an alkyl group containing 1 to 16 carbon atoms. Among these products, particularly preferred products are those in which R represents a C1-C4 lower alkyl group (more specifically, a methyl group).

[0435] Among these resins, one may mention those sold under the name Dow Corning 593 or those sold by General Electric under the names Silicone Fluids SS 4230 and SS 4267, which are silicones having a dimethyl / trimethylsiloxane structure.

[0436] Also worth mentioning are the trimethylsiloxysilicate type resins sold by Shin-Etsu Corporation under the names X22-4914, X21-5034, and X21-5037.

[0437] Among other organically modified silicones, polyorganosiloxanes can be mentioned, including:

[0438] - Substituted or unsubstituted amine groups, such as those sold by Dow Corning under the names Q2 8220 and Dow Corning 929 or 939. The substituted amino groups are particularly C1-C4 aminoalkyl groups;

[0439] -Alkoxylation groups, for example, those produced by Goldschmidt under the name Abil Products sold in 2428, 2434 and 2440.

[0440] Non-liquid fatty ethers are selected from dialkyl ethers alone or as a mixture, and especially diceryl ether and distearate ether.

[0441] The compositions according to the invention may contain one or more of the same or different butters, preferably plant-derived butters.

[0442] According to a preferred embodiment of the invention, C 16 The weight content of fatty acid triglycerides, expressed relative to the total amount of fatty acid triglycerides in the lipids according to the invention, is less than 23%.

[0443] For the purposes of this invention, the term "lipid" (also known as "paste-like fatty substance") refers to a lipophilic fatty compound that undergoes a reversible solid / liquid phase change and comprises both liquid and solid portions at a temperature of 25°C and atmospheric pressure (760 mmHg). In other words, the initial melting point of the paste-like compound may be less than 25°C. The liquid portion of the paste-like compound, measured at 25°C, may account for 9% to 97% by weight of the compound. This portion, which is liquid at 25°C, preferably accounts for 15% to 85% by weight, more preferably 40% to 85% by weight.

[0444] Preferably, the grease has an endpoint melting point below 60°C.

[0445] Preferably, the grease has a hardness of less than or equal to 6 MPa.

[0446] Preferably, the pasty fatty substance, when in a solid state, has an anisotropic crystalline structure visible to X-rays.

[0447] For the purposes of this invention, the melting point corresponds to the temperature at which the maximum endothermic peak is observed in thermal analysis (DSC), as described in standard ISO 11357-3;1999. The melting point of a paste or wax can be measured using a differential scanning calorimeter (DSC), such as the calorimeter sold by TA Instruments under the name DSC Q2000.

[0448] The sample preparation and measurement procedures for measuring melting point and determining endpoint melting point are as follows:

[0449] A 5 mg sample of the paste-like fatty substance was preheated to 80°C and removed using a heated spatula under magnetic stirring. The sample was then placed in a sealed aluminum capsule or crucible. Two tests were performed to ensure reproducibility of the results.

[0450] Measurements were performed on the aforementioned calorimeter. The oven was purged with nitrogen. Cooling was performed using an RCS 90 heat exchanger. The sample was then subjected to the following procedure: it was first placed at 20°C, and then subjected to a first temperature rise from 20°C to 80°C (at a heating rate of 5°C / min), then cooled from 80°C to -80°C (at a cooling rate of 5°C / min), and finally subjected to a second temperature rise from -80°C to 80°C (at a heating rate of 5°C / min). During the second temperature rise, the change in the energy difference absorbed by the empty crucible and the crucible containing the lipid sample was measured as a function of temperature. The melting point of the compound is the temperature value corresponding to the peak of the curve representing the change in the energy difference absorbed with temperature.

[0451] The endpoint melting point corresponds to the temperature at which 95% of the sample melts.

[0452] At 25°C, the liquid portion of the grease by weight is equal to the ratio of the enthalpy of melting consumed at 25°C to the enthalpy of melting of the grease.

[0453] The heat of fusion of a paste-like compound is the amount of heat required for the compound to change from a solid to a liquid state. A fat is said to be in a solid state when its entire mass is in crystalline solid form. A fat is said to be in a liquid state when its entire mass is in liquid form.

[0454] The heat of fusion of a fat is equal to the integral of the entire melting curve obtained using the calorimeter described above, according to standard ISO 11357-3:1999, where the temperature rises by 5°C or 10°C per minute. The heat of fusion of a fat is the amount of energy required to change a compound from a solid to a liquid state. It is expressed in J / g.

[0455] The heat of fusion consumed at 25°C is the amount of energy absorbed by a sample as it changes from a solid state to a state consisting of liquid and solid parts at 25°C.

[0456] The liquid portion of the fat, measured at 32°C, preferably accounts for 30% to 100% by weight, more preferably 50% to 100% by weight, and more preferably 60% to 100% by weight of the compound. When the liquid portion of the fat, measured at 32°C, is equal to 100%, the endpoint temperature of the melting range of the paste compound is less than or equal to 32°C.

[0457] The liquid portion of a fat measured at 32°C is equal to the ratio of the heat of fusion consumed at 32°C to the heat of fusion of the paste-like compound. The heat of fusion consumed at 32°C is calculated in the same manner as the heat of fusion consumed at 23°C.

[0458] Regarding the measurement of hardness, the sample preparation and measurement procedures are as follows:

[0459] The composition or grease according to the invention is placed in a mold with a diameter of 75 mm, and the mold is filled to about 75% of its height. To overcome thermal history and control crystallization, the mold is placed... In the VC0018 programmable oven, it is first placed at a temperature of 80°C for 60 minutes, then cooled from 80°C to 0°C (at a cooling rate of 5°C / min), and then left to stand at a stable temperature of 0°C for 60 minutes, and then subjected to a temperature increase ranging from 0°C to 20°C (at a heating rate of 5°C / min), and then left to stand at a stable temperature of 20°C for 180 minutes.

[0460] Compressibility force was measured using a TA / TX2i texture meter from Swantech. The spindle used was selected based on the texture.

[0461] - A cylindrical steel spindle with a diameter of 2mm, used for very hard starting materials;

[0462] - A cylindrical steel spindle with a diameter of 12mm, used for starting materials that are not very hard.

[0463] The measurement includes three steps:

[0464] - The first step after automatic detection of the sample surface, wherein the spindle moves at a measuring speed of 0.1 mm / s and penetrates into the composition or grease according to the invention to a penetration depth of 0.3 mm, and the software records the maximum force value reached;

[0465] - The second step, called relaxation, involves holding the spindle in this position for one second and recording the force after one second of relaxation; and finally...

[0466] - The third step, called extraction, involves the spindle returning to its original position at a speed of 1 mm / s, and the extraction energy (negative force) of the spindle is recorded.

[0467] The hardness value measured during the first step corresponds to the maximum compressive force measured in Newtons divided by the force in mm that comes into contact with the grease or composition according to the invention. 2 The area of ​​the material gauge cylinder is represented. The obtained hardness value is expressed in megapascals (MPa).

[0468] According to a preferred mode of the invention, the specific lipids are of plant origin, such as those described in Ullmann's Encyclopedia of Industrial Chemistry ("Fats and Fatty Oils", A. Thomas, online publication: June 15, 2000, DOI:10.1002 / 14356007.a10_173, point 13.2.2.2. Butter, Borneo lipids and related fats (vegetable lipids)).

[0469] More specifically, one could mention shea butter, Nilotica (Butyrospermum parkii) shea butter, shea butter (butyrospermum parkii), Borneo resin or fat or Shoreastenoptera resin, Borneo resin, madhuca butter, Madhuca resin or Brazilian madhuca longifolia resin, basil seed resin (Madhucalatifolia), katiau resin (Madhuca mottleyana), phulwara resin (M. butyracea), mango resin (Mangifera indica), Astrocaryum murumuru resin, Garcinia indica seed resin, and cinnamon wax resin (Virola). Sebifera (), tucuma oil, paina oil (Kpangnan) (Pentadesma butyracea), coffee oil (Coffea arbica), apricot oil (Prunus armeniaca), macadamia oil (Macadamia ternifolia), grape seed oil (Vitis vinifera), avocado oil (Perseagratissima), olive oil (Olea europaea), sweet almond oil (Prunus amygdalusdulcis), and sunflower oil. Preferably, the oils according to the invention are selected from star palm oil, yellow wax resin, borax resin, sage oil, shea butter, and gupuasoo oil, and even more preferably shea butter.

[0470] In a preferred variant of the invention, C 16The weight content of fatty acid triglycerides, expressed relative to the total amount of fatty acid triglycerides, ranges from 0 to 22%, preferably less than 0 to 15%, and even more preferably 2% to 12%.

[0471] The composition according to the invention comprises one or more lipids in an amount particularly comprising, from 0.01% to 30% by weight, more particularly comprising, from 0.1% to 20% by weight, preferably comprising, from 0.5% to 10% by weight, and more preferably comprising, from 1% to 5% by weight, relative to the total weight of the composition.

[0472] Preferably, the composition of the present invention contains one or more components that are present at room temperature (25°C) and atmospheric pressure (760 mmHg; i.e., 1.013 × 10⁻⁶). 5 The fatty substance that is liquid under the conditions of Pa) may optionally be combined with one or more fatty substances that are non-liquid under the same conditions.

[0473] Preferably, the fatty substances are selected from

[0474] a) Fat, preferably shea butter;

[0475] b) Wax, preferably beeswax;

[0476] c) Non-liquid fatty alcohols, particularly selected from saturated or unsaturated, straight-chain or branched alcohols containing 8 to 30 carbon atoms – said alcohols are preferably C14-30 ... 10 -C 22 alcohol, more preferably C 14 -C 20 Alcohol, and even better C 16 -C 18 Alcohols, such as cetyl alcohol and stearyl alcohol—and mixtures thereof;

[0477] d) Non-liquid fatty acid esters and / or fatty alcohol esters, especially those derived from C9-C 26 Fatty acids and C9-C 26 Solid esters of fatty alcohols, especially alkyl esters of myristate, such as cetyl myristate, myristyl myristate or stearyl myristate, hexyl stearate, and more particularly myristate myristate.

[0478] e) Esters of monohydric alcohols, wherein at least one of the alcohols or acids from which the ester is derived is branched, such as ethyl palmitate, isopropyl palmitate, alkyl myristate esters such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isodecanyl neopentanoate, isostearyl neopentanoate, and C 10 -C 22 Preferably C 12 -C 20 Alkyl (iso)stearates, such as isopropyl isostearate;

[0479] f) Cyclic polydialkylsiloxanes containing 3 to 7, preferably 4 to 5, silicon atoms, such as octamethylcyclotetrasiloxane, decamethylcyclopentane, dodecylcyclopentane, or cyclohexanedimethylsiloxane, and mixtures thereof, preferably cyclohexanedimethylsiloxane.

[0480] g) Plant-derived oils or synthetic triglycerides, such as liquid triglycerides of fatty acids containing 6 to 30 carbon atoms, for example, heptanoic acid or caprylic acid triglycerides, or alternatives such as sunflower oil, corn oil, soybean oil, marrow oil, grape seed oil, sesame seed oil, hazelnut oil, almond oil, macadamia nut oil, arabac oil, sunflower oil, castor oil, avocado oil, caprylic / capric acid triglycerides, jojoba oil, shea butter, preferably caprylic / capric acid triglycerides.

[0481] The fatty substances used in the compositions according to the invention may be present in the composition in an amount ranging from 1% to 40% by weight, preferably from 5% to 30% by weight, and even more preferably from 10% to 20% by weight relative to the total weight of the composition.

[0482] vi) Alkaline agents:

[0483] According to specific embodiments of the present invention, the composition of the present invention comprises vi) one or more alkaline agents (also called alkalis). This agent may be selected from inorganic or organic or mixed alkalis or mixtures thereof.

[0484] The inorganic alkaline agent is preferably selected from ammonia, alkaline carbonates or bicarbonates such as sodium carbonate or potassium carbonate and sodium bicarbonate or potassium bicarbonate, sodium hydroxide or potassium hydroxide, or mixtures thereof.

[0485] According to an advantageous embodiment of the invention, one or more alkali agents are organic amines, i.e., they contain at least one substituted or unsubstituted amino group.

[0486] Organic alkaline agents are more preferably selected from those having a pK value of less than 12, preferably less than 10, and even more advantageously less than 6 at 25°C. b Organic amines. It should be noted that this corresponds to the pK value of the functional group with the highest basicity. b .

[0487] Hybrid compounds that may be mentioned include salts of amines and acids such as carbonic acid or hydrochloric acid, as previously mentioned.

[0488] Organic basic agents are selected from, for example, alkanolamines, oxyethylated and / or oxypropyleneated ethylenediamines, amino acids, and compounds of formula (IV):

[0489]

[0490] In equation (IV):

[0491] -W is a divalent C1-C6 alkylene group, optionally substituted with a hydroxyl group or a C1-C6 alkyl group, and / or optionally substituted with one or more heteroatoms such as oxygen or NR. u insert;

[0492] -R x R y R z R t and R u The same or different indicates a hydrogen atom or a C1-C6 alkyl, C1-C6 hydroxyalkyl, or C1-C6 aminoalkyl.

[0493] Examples of such amines that may be mentioned include 1,3-diaminopropane, 1,3-diamino-2-propanol, spermine, and spermidine.

[0494] The term "alkanolamine" refers to an organic amine that contains primary, secondary or tertiary amine functional groups and one or more straight-chain or branched C1-C8 alkyl groups with one or more hydroxyl groups.

[0495] Alkanolamines, such as monoalkanolamines, dialkanolamines, or trialkanolamines containing one to three identical or different C1-C4 hydroxyalkyl groups, are particularly suitable for carrying out the present invention.

[0496] Among compounds of this type, those that may be mentioned are monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N-dimethylaminoethanolamine, 2-amino-2-methyl-1-propanol, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 3-amino-1,2-propanediol, 3-dimethylamino-1,2-propanediol, and tris(hydroxymethylamino)methane.

[0497] More specifically, the amino acids that can be used are of natural or synthetic origin, in their L, D, or racemic forms, and contain at least one acid functional group selected more specifically from the following: carboxylic acids, sulfonic acids, phosphonic acids, and phosphate functional groups. Amino acids can be in neutral or ionic form.

[0498] Among the amino acids that can be used in this invention, aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine, and valine are particularly noteworthy.

[0499] Advantageously, the amino acid is a basic amino acid containing an additional amine functional group (optionally contained in a cyclic or ureidofunctional group), particularly selected from histidine, lysine, arginine, ornithine and citrulline.

[0500] Organic amines can also be selected from heterocyclic organic amines. In addition to histidine, which has already been mentioned in the section on amino acids, pyridine, piperidine, imidazole, triazole, tetraazole, and benzimidazole are particularly noteworthy.

[0501] Organic amines can also be selected from amino acid dipeptides. Among the amino acid dipeptides that can be used in this invention, carnosine, anserine, and balenine are particularly noteworthy.

[0502] The organic amine is selected from compounds containing a guanidine functional group. In addition to arginine, which has already been mentioned as an amino acid, creatine, creatine anhydride, 1,1-dimethylguanidine, 1,1-diethylguanidine, guanidinoacetic acid, metformin, guanidinobutylamine, n-amidinylalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid, and 2-([amino(imino)methyl]amino)ethane-1-sulfonic acid are also noteworthy examples of amines that can be used in this invention.

[0503] In particular, the use of guanidine carbonate or monoethanolamine hydrochloride as a hybrid compound can be mentioned.

[0504] The compositions of the present invention preferably contain one or more alkanolamines and / or one or more basic amino acids, more advantageously one or more alkanolamines. Even more preferably, the organic amine is a monoethanolamine.

[0505] According to specific embodiments, the compositions of the present invention contain one or more alkanolamines as basic agents.

[0506] Preferably, the alkanolamine is triethanolamine.

[0507] Advantageously, the composition according to the invention has an alkaline agent in a content ranging from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and even more preferably from 0.1% to 1% by weight relative to the composition.

[0508] Composition

[0509] The subject of this invention is a composition comprising:

[0510] i) one or more 4-(3-ethoxy-4-hydroxyphenyl)but-2-one compounds as defined above;

[0511] ii) one or more preservatives as defined above, different from i) and / or one or more antioxidants, preferably 4-hydroxyacetophenone;

[0512] iii) One or more surfactants selected from nonionic, anionic, and amphoteric surfactants;

[0513] iv) one or more thickening polymers as defined above, preferably organic; and v) optionally one or more fatty substances as defined above.

[0514] According to one variant of the invention, the composition comprises:

[0515] i) one or more 4-(3-ethoxy-4-hydroxyphenyl)but-2-one compounds as defined above;

[0516] ii) One or more preservatives different from i);

[0517] iii) One or more surfactants selected from nonionic, anionic, and amphoteric surfactants;

[0518] iv) one or more thickening polymers as defined above, preferably organic; and v) optionally one or more fatty substances as defined above.

[0519] According to one variant of the invention, the composition comprises:

[0520] i) one or more 4-(3-ethoxy-4-hydroxyphenyl)but-2-one compounds as defined above;

[0521] ii) one or more antioxidants as defined above, preferably 4-hydroxyacetophenone;

[0522] iii) One or more surfactants selected from nonionic, anionic, and amphoteric surfactants;

[0523] iv) one or more thickening polymers as defined above, preferably organic; and v) optionally one or more fatty substances as defined above.

[0524] According to yet another variant of the invention, the composition comprises:

[0525] i) one or more 4-(3-ethoxy-4-hydroxyphenyl)but-2-one compounds as defined above;

[0526] ii) one or more preservatives as defined above, different from i), and one or more antioxidants, preferably 4-hydroxyacetophenone;

[0527] iii) One or more surfactants selected from nonionic, anionic, and amphoteric surfactants;

[0528] iv) one or more thickening polymers as defined above, preferably organic; and v) optionally one or more fatty substances as defined above.

[0529] The composition is a physiologically acceptable medium. The composition is particularly suitable for cosmetic, pharmaceutical, or dermatological compositions. It can also be a food (nutritional) composition.

[0530] Physiologically acceptable mediators:

[0531] The term "physiologically acceptable medium" refers to a medium suitable for application to keratin materials, also known as a formulation carrier, which is a cosmetic or pharmaceutical medium typically composed of water or a mixture of water and one or more organic solvents. Preferably, the composition contains water, in particular in an amount including, but not limited to, 5% to 99.9% by weight relative to the total weight of the composition, more preferably 10% to 90% by weight relative to the total weight of the composition, and even more preferably including, in an amount including, but not limited to, 20% to 80% by weight.

[0532] Organic solvents:

[0533] The term "organic solvent" refers to an organic substance that can dissolve another substance without chemically altering it.

[0534] Examples of organic solvents that may be mentioned include: a) C2-C6 alkanols, such as ethanol and isopropanol; b) polyols miscible with water at room temperature (25°C), particularly selected from polyols containing 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1,3-propanediol, butanediol, pentanediol, hexanediol, dipropylene glycol, diethylene glycol, or diglycerol; c) polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, or diethylene glycol monomethyl ether; and d) aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0535] According to specific embodiments, the composition further comprises one or more polyols, particularly selected from polyols containing 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms, such as glycerol.

[0536] In a preferred embodiment, 4-(3-ethoxy-4-hydroxyphenyl)but-2-one is used in combination with an effective amount of at least one organic solvent, which may be selected from ethanol, 1,2-propanediol, 1,3-propanediol, PEG-8 (polyethylene glycol containing 8 ethylene glycol units), propylene carbonate, dipropylene glycol, 1,2-hexanediol, and PEG-4.

[0537] Preferably, the organic solvent is selected from ethanol, 1,2-propanediol, 1,3-propanediol, PEG-8 and propylene carbonate.

[0538] Advantageously, the composition according to the invention comprises 1,3-propanediol, the content of which ranges from 0.1 wt% to 20 wt%, preferably from 0.1 wt% to 10 wt%, and most preferably from 0.5 wt% to 5 wt%, in particular relative to the total weight of the composition.

[0539] For food compositions, water and those suitable for consumption as organic solvents, such as ethanol, are preferred.

[0540] The organic solvent is preferably present in a proportion that includes approximately 0.1% to 40% by weight, more preferably approximately 1% to 20% by weight, and even more particularly 5% to 10% by weight, relative to the total weight of the composition.

[0541] pH:

[0542] The pH of the compositions according to the invention is generally from about 2 to 12, and preferably from about 3 to 11, including the extreme values. It can be adjusted to the desired value by means of acidifying or alkaline agents commonly used in keratin fiber staining, or alternatively by using a standard buffer system.

[0543] The pH of the composition is preferably from 4.5 to 10, particularly from 6 to 9, more particularly from 7 to 9, and even more particularly from about neutral pH 7.

[0544] Examples of acidifying agents that may be mentioned include inorganic or organic acids as defined above, especially hydrochloric acid, phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acid.

[0545] Examples of alkalis or alkaline agents that may be mentioned include ammonia, alkali metal carbonates, alkanolamines, and other alkaline agents as defined below, preferably alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine.

[0546] Preferably, the composition comprises i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one and its organic or inorganic acid salts or base salts, and its solvates such as hydrates, in an amount ranging from 0.02% to 2% by weight, preferably from 0.03% to 1% by weight, and even more preferably from 0.04% to 0.8% by weight, relative to the total weight of the composition.

[0547] The subject of this invention is also a composition comprising the previously described antimicrobial mixture in a physiologically acceptable medium.

[0548] The term "physiologically acceptable medium" refers to a medium that is compatible with human keratin materials such as skin, scalp, nails, and keratin fibers such as hair.

[0549] The medium may contain one or more additional components different from components i) and ii).

[0550] The composition may contain one or more additional ingredients or auxiliaries selected from the following: gelling agents other than organic thickening polymers as defined above; non-anionic, cationic, nonionic or amphoteric, natural or synthetic, film-forming or non-film-forming non-thickening polymers; coloring materials such as organic or inorganic pigments; fragrances; fillers; UV shielding agents; plant extracts; cosmetic and dermatological active agents; and salts.

[0551] The compositions according to the invention can be in the following forms: oil-in-water (O / W) emulsions, water-in-oil (W / O) emulsions or multiple emulsions (triple: W / O / W or O / W / O), oily solutions, oily gels, aqueous solutions, aqueous gels, or solid compositions. The compositions of the invention are prepared according to commonly used methods.

[0552] The compositions according to the invention preferably contain water, i.e., are aqueous. According to one embodiment of the invention, the composition comprises an aqueous phase and an organic or oil phase. Preferably, the compositions of the invention are O / W type direct emulsions.

[0553] The compositions according to the invention can be generally fluid and can have the appearance of a white or colored cream, ointment, emulsion, lotion, serum, paste, or foam. They can optionally be applied to the skin in aerosol form. They can also be in solid form, for example, in the form of sticks or dense powder.

[0554] The compositions according to the invention can be, in particular, in the following forms:

[0555] - Cosmetic products, especially for applying makeup to the face, body skin, lips, or eyelashes;

[0556] - Gel or lotion for after shaving; shaving products;

[0557] - Deodorants (sticks, roll-ons, or aerosols);

[0558] - Hair removal cream;

[0559] -Body care compositions, such as shower gels or shampoos;

[0560] - Pharmaceutical composition;

[0561] - Solid compositions such as soap or cleaning sticks;

[0562] - The aerosol composition also contains a pressurized propellant;

[0563] - Hair styling lotions, hair styling creams or gels, coloring compositions, compositions for permanent waves, lotions or gels to combat hair loss, or hair conditioners;

[0564] - A composition for caring for or cleaning the skin.

[0565] Methods for preparing the composition:

[0566] The subject of this invention is also a method for preparing compositions, particularly cosmetic, pharmaceutical, or food compositions, the method comprising the step of mixing the following: i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one, or a base salt or solvation thereof, ii) 4-hydroxyphenyl ethyl one, or a base salt or solvation thereof, and optionally one or more additional ingredients or adjuvants, particularly cosmetic, pharmaceutical, or food ingredients or adjuvants, such as those previously described, and optionally water, and one or more organic solvents.

[0567] Antimicrobial activity and its uses:

[0568] The mixtures i) and ii) according to the invention exhibit valuable antimicrobial activity, particularly synergistic antimicrobial activity, against fungi, especially against the species Candida albicans, in water treatment. Specifically, fungi represent one of the sources of water pollution, as mentioned in the following article: "Fungal Contaminants in drinking water regulation? A tale of ecology, exposure, purification and clinical relevance" Int. J. Environ. Res. Public Health, 2017, 14, 636.

[0569] The present invention also relates to the use of antimicrobial mixtures in water treatment, wherein the water is selected from domestic or industrial water, water from aquatic media, swimming pool / thermal water, and water from air conditioning systems.

[0570] The term "water treatment" refers to continuous or discontinuous (intermittent) treatment, which includes adding substances to a water sample or stream of water to be treated for the purpose of preventing water from being contaminated by contaminants or partially or completely purifying the water to be treated of the contaminants.

[0571] Preferably, water treatment in the context of this invention includes continuously or discontinuously adding substances to a water sample or a water stream to be treated in order to partially or completely purify contaminants in the water to be treated.

[0572] Contaminants can be microorganisms, especially bacteria and / or fungi.

[0573] Even more preferably, the water treatment is the treatment of water contaminated with one or more microorganisms, preferably with Gram-positive or Gram-negative bacteria or fungi of the species Enterococcus faecalis, Candida albicans, or Pseudomonas aeruginosa.

[0574] The term "water from aquatic media" refers to water from lakes, tributaries, pools, main rivers, oceans or ocean bathing areas, groundwater such as well water, surface water, and aquarium water.

[0575] For the purposes of this invention, “domestic or industrial water” includes wastewater before it is treated in a purification device, water treated in a purification device, water before it is treated in a drinking water device, water treated in a drinking water device, and water circulated in a potable or non-potable urban network, such as water circulated in pipes.

[0576] The present invention also relates to a continuous or discontinuous water treatment method, the method comprising at least one step of placing a water sample or a water stream to be treated in contact with an antimicrobial mixture according to the present invention, wherein the water to be treated is selected from domestic or industrial water, water from aquatic media, swimming pool / thermal water, and water from an air conditioning system.

[0577] Preferably, the step of placing the water to be treated in contact with the antimicrobial mixture according to the invention can be carried out, in particular, by injecting the compound in liquid form, by using a filter or filter cartridge containing the compound, or by applying the compound in solid form, particularly in the form of granules, tablets or pellets.

[0578] i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one, as well as its organic or inorganic acid salts or base salts, and its solvates such as hydrates, may be used at a ratio of at least 0.06% by weight, preferably at least 0.1% by weight, and even more preferably at least 0.5% by weight relative to the total weight of the water to be treated. In one specific embodiment, a compound of formula (I) or (I') or a solvate such as a hydrate thereof may be used at a ratio of at least 1% by weight relative to the total weight of the water to be treated.

[0579] i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one, as well as its organic or inorganic acid salts or base salts, and its solvates such as hydrates, may be used at concentrations ranging from 0.06 wt% to 10 wt%, preferably 0.1 wt% to 5 wt%, and even more preferably 0.5 wt% to 2 wt%, relative to the total weight of the water to be treated. In a preferred embodiment, 4-(3-ethoxy-4-hydroxyphenyl)but-2-one may be used at concentrations ranging from 0.1 wt% to 1 wt%, relative to the total weight of the water to be treated.

[0580] The solvent can be used in a concentration ranging from 0.05% to 10% by weight relative to the total weight of the water to be treated, preferably from 0.1% to 5% by weight and more preferably from 0.1% to 2.5% by weight relative to the total weight of the water to be treated.

[0581] The invention is illustrated in more detail in the following examples. The content of the ingredients is expressed as a weight percentage.

[0582] Example

[0583] Example 1: Determining the synergistic antimicrobial activity as a MIC

[0584] The synergistic antimicrobial activity of a mixture of 4-(3-ethoxy-4-hydroxyphenyl)but-2-one (referred to as Substance A) and an alcohol compound (referred to as Substance B) was demonstrated by calculating the synergistic index (or FIC index) according to the following formula:

[0585] [Mathematical Expression 1]

[0586] FIC index = (MIC of A and B / MIC of A) + (MIC of B and A / MIC of B)

[0587] in:

[0588] -MIC of A and B: The minimum concentration of product A in the combination A+B that enables the inhibitory effect;

[0589] -MIC of B and A: The minimum concentration of product B in the combination A+B that enables the inhibition effect.

[0590] -MIC of A: The minimum inhibitory concentration of product A alone;

[0591] -MIC of B: The minimum inhibitory concentration of product B alone.

[0592] The formula was first described in the following article: FCKull, PCEisman, HDSylwestrowka, and RLMayer, Applied Microbiology 9:538-541, 1961.

[0593] For each individual compound tested, the MIC is considered to be the first concentration that enables the attainment of a microbial growth percentage of less than or equal to 25%.

[0594] For the tested combinations, the MICs of A and B, and the MICs of B and A, are the concentrations of A and B in the combinations that enable the achievement of a microbial growth percentage of less than or equal to 25%.

[0595] Explanation of the FIC Index :

[0596] When the FIC index value is less than or equal to 1, the combination of test compounds is considered to have a synergistic effect.

[0597] The results are summarized in the table below.

[0598] The combination of compounds A and B, as well as compositions containing the combination, were tested on the following strains or portions thereof: Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans.

[0599] The microbial strain Aspergillus niger ATCC 6275 was used, along with polyoxyethylene-modified (20OE) sorbitol monopalmitate (from Croda's Tween 40) and BioReagent supplemented with double-concentration Sabouraud broth liquid medium (i.e., a mixture of 5g Phytagel + 0.6g Tween 40 + 60g Sabouraud broth).

[0600] The microbial strain Staphylococcus aureus ATCC 6538 and double-concentrated nutrient broth liquid medium were used.

[0601] The microbial strain Candida albicans ATCC 10231 and double-concentrated Sabouraud broth liquid medium (i.e., a mixture of 5 g Phytagel + 0.6 g Tween 40 + 60 g Sabouraud broth) were used.

[0602] 96-well microplates were used with an incubation temperature of 32.5°C.

[0603] The incubation time for the microplate is:

[0604] - For Aspergillus niger ATCC 6275, 24 to 30 hours under aerobic conditions;

[0605] - For Candida albicans ATCC 10231, Pseudomonas aeruginosa ATCC 9027 and Staphylococcus aureus ATCC6538, under aerobic conditions for 18 to 24 hours;

[0606] test

[0607] For each compound:

[0608] A = Compound i) 4-(3-ethoxy-4-hydroxyphenyl)but-2-one

[0609] B = Compound ii) Preservatives and / or antioxidants:

[0610] B1: 4-Hydroxyacetophenone, B2: Salicylic acid

[0611] Testing of compounds A and B individually

[0612] 50 μl of each of the obtained sub-solutions containing compound A or B was added to the wells of the microplate. 100 μl of Sabouraud broth and 50 μl of solution containing a double concentration of Aspergillus niger strain were also added.

[0613] Tests of compounds A and B as a mixture

[0614] 50 μl of each subsolution containing compound A and 50 μl of each subsolution containing compound B were added to the wells of the microplate. 100 μl of Sabouraud broth containing the inoculated strain Aspergillus niger at a double concentration was also added.

[0615] Microbial growth control

[0616] A positive microbial growth control was also prepared. The positive microbial growth control corresponded to a mixture of 100 μl of 1‰ agar aqueous solution and 100 μl of Sabouraud liquid nutrient broth inoculated with Aspergillus niger at double the concentration, in the absence of compounds A and B.

[0617] Absorbance comparison of compounds A and B alone

[0618] Absorbance controls were performed in parallel on individual compounds A and B. This control corresponded to 100 μl of double-concentration sterile Sabouraud broth + 100 μl of double-concentration compound A or B.

[0619] In all three cases (absorbance control, growth control, and testing), the final volume present in each microplate well was 200 μl.

[0620] In both cases (test and control), the inoculum represents the concentration of Aspergillus niger strain present in the final volume (200 μl) of the well, and is 2 to 6 × 10⁻⁶. 5 Aspergillus niger at cfu / ml.

[0621] The minimum inhibitory concentrations (MICs) of compounds A and B, individually or in combination, were determined in a known manner by optical density measurements at a wavelength of 620 nm.

[0622] Perform the tests described above again (test, absorbance control, and growth control) to test combination A+B on the following strains: Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans.

[0623] The following results were obtained, where compound B1 = 4-hydroxyphenyl ethyl ketone:

[0624] Antimicrobial properties were also evaluated with other compositions, those detailed in Table 3 below, where the components are given as weight (g) / 100g of composition. Properties were evaluated at 7 days, 14 days, and 1 month.

[0625] [Table 1]

[0626]

[0627]

[0628] The results for the Escherichia coli strain at 7 days are shown in the table below:

[0629] [Table 2]

[0630] Composition Microbial count after 7 days Composition 1 (of the present invention) <200 Composition 2 (Comparative) <![CDATA[2.4×10 4 ]]> Composition 3 (Comparative) <![CDATA[2.1×10 5 ]]>

[0631] The results for the Staphylococcus aureus strain at 7 and 14 days are given in the table below:

[0632] [Table 3]

[0633]

[0634] The results for other microbial strains at 7 days, 14 days, and then 1 month are given in the table below:

[0635] [Table 4]

[0636]

[0637] The results in the table above show that the combination of A and B1 according to the present invention allows for significant antimicrobial improvement against a variety of microbial strains (Aspergillus niger, Escherichia coli, Staphylococcus aureus and Candida albicans), after 7 days, 15 days or even 1 month.

[0638] The following composition was prepared, wherein ii) compound B2 = salicylic acid:

[0639] [Table 5]

[0640]

[0641]

[0642] It can be seen that the comparative composition 5, containing a cationic surfactant, is much less stable than the composition 4 according to the invention. Furthermore, the viscosity of composition 4 according to the invention is 32.5 poise, while the comparative composition 5 is much more viscous, having a viscosity of 51.5 poise. These viscosity values ​​were measured at 25°C and atmospheric pressure.

[0643] Other comparative tests:

[0644] The following two compositions were prepared: the amounts of these components are given in g / 100g of composition:

[0645] [Table 6]

[0646]

[0647]

[0648] The composition according to the invention is glossy, aerated, white, and has a "basic" odor.

[0649] Microscopic evaluation of the composition:

[0650] Under a white light microscope at 400x magnification (Leica DM2500 with Archimed Microvision software), it was observed that the control composition 6 contained vacuoles, while the composition 7 according to the invention was more structured, with no visible vacuoles, making it more stable.

[0651] Sensory evaluation:

[0652] The application of composition 7 of the present invention is more refreshing, easier, stickier and better, and the pleasure obtained by rubbing the fingers on the skin is significantly longer than that obtained with composition 6.

[0653] After applying composition 7 according to the invention to the skin, a much more matte and soft-focus appearance can be seen than that obtained with comparative composition 6.

[0654] Measurement of soft-focus / matte effect on keratin materials:

[0655] To measure transmittance, haze, and brightness, a Byk haze meter, model: HazeGard Plus, was used.

[0656] The matte / soft-focus effect after application to the skin, as determined by the evaluation panel, was confirmed through measurements of transmittance, haze, brightness, and gloss. To quantify the transmitted light of the formulation and its soft-focus capabilities, the "haze" parameter was measured. Haze measurement involves determining the amount of light deflected from its trajectory by the sample. This allows for the quantification of the material's soft-focus capabilities.

[0657] Research conditions: room temperature: 25℃, membrane drying temperature: 25℃, membrane drying time: 1h.

[0658] Elcometer Fabric Spreader: Model: 4340 - Place a transparent 100-micron sheet on the fabric spreader, adjust to a thickness of 25 microns, then add the sample, and then allow the film to dry at room temperature for 1 hour. Then place the transparent sheet coated with the 25-micron-thick sample onto the lens of the device, and measure the H (haze) and B (brightness) values.

[0659] To measure gloss, a Byk Micro TRI gloss meter was used. The application was the same as described above, with the measurement performed directly using a transparent sheet placed on a black surface and the gloss meter.

[0660] [Table 7]

[0661] Observation / Measurement Comparative composition 6 Composition 7 (of the present invention) Haze 22.77 53.28 brightness 48.15 12.15 luster 40.32 18.65

[0662] As can be seen from the results in Table 7, compared with the comparative composition, the composition according to the present invention (composition 7) enables a significant improvement in soft focus and matte finish.

Claims

1. A mixture comprising: i) 0.02-2% by weight of one or more 4-(3-ethoxy-4-hydroxyphenyl)but-2-one compounds or one or more organic or inorganic base salts thereof; ii) One or more preservatives and / or one or more antioxidants different from i); wherein the one or more preservatives or one or more antioxidants are selected from: 4-hydroxyacetophenone and its base salts; iii) One or more surfactants; iv) One or more thickening polymers; and optionally v) One or more fatty substances; When the mixture contains one or more cationic surfactants, their amounts are less than 3% by weight relative to the total weight of i) to v). The weight ratio i) / ii) is 2 to 4.

2. The mixture of claim 1, wherein, The weight ratio i) / ii) ranges from 3 to 3.

8.

3. The mixture of the preceding claim 1 or 2, wherein, The mixture contains less than 0.5% by weight of surfactant relative to the total weight of i) to v).

4. A composition comprising a mixture of components i), ii), iii) and iv) as defined in any one of claims 1 to 3 and optionally v), said composition comprising a cationic surfactant in an amount of less than 0.5% by weight relative to the total weight of said composition.

5. The composition of claim 4, comprising one or more surfactants selected from nonionic and anionic surfactants and mixtures thereof.

6. The composition of any one of claims 4 and 5, comprising one or more nonionic surfactants selected from: (poly)ethoxylated fatty alcohols; glycerolized fatty alcohols; alkyl polyglycosides; oxyethylated fatty acid monoesters and diesters of sorbitol containing 2 to 200 mol of EO; or mixtures thereof.

7. The composition of any one of claims 4 to 5, comprising one or more anionic surfactants selected from: alkyl carboxylic acids, alkyl sulfates, alkyl ether sulfates, alkyl amide ether sulfates, alkyl aryl polyether sulfates, glyceryl monoester sulfates, alkyl sulfonates, alkyl amide sulfonates, alkyl aryl sulfonates, α-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl amide sulfosuccinates, alkyl sulfoacetates, acyl sarcosinates, acyl glutamates, alkyl sulfosuccinates, acyl hydroxyethyl sulfonates and N-acyl taurates, salts of alkyl monoesters of polyglycoside-polycarboxylic acids, salts of alkyl diesters of polyglycoside-polycarboxylic acids, acyl lactylates, D-galactoside-uronic acid salts, alkyl ether carboxylates, alkyl aryl ether carboxylates, alkyl amide ether carboxylates, and the corresponding unsalted forms of all these compounds, wherein the alkyl and acyl groups of all these compounds comprise 8 to 30 carbon atoms, and the aryl group represents a phenyl group that can be oxyethylated.

8. The composition of any one of claims 4-5, wherein, The amount of surfactant ranges from 0.5% by weight to 30% by weight relative to the total weight of the composition of the present invention.

9. The composition according to any one of claims 4 to 5, comprising one or more fatty substances selected from: a) fat; b) Wax; c) Non-liquid fatty alcohols and mixtures thereof; d) Non-liquid fatty acid esters and / or fatty alcohol esters; e) An ester of a monohydric alcohol, wherein at least one of the alcohols or acids derived from the ester is branched; f) Cyclic polydialkylsiloxanes containing 3 to 7 silicon atoms, and mixtures thereof; g) Plant-derived oils or synthetic triglycerides.

10. The composition of any one of claims 4 to 5, comprising one or more fatty substances, wherein the amount of the fatty substances ranges from 1% by weight to 40% by weight relative to the total weight of the composition.

11. The composition of any one of claims 4 to 5, comprising one or more thickening organic polymers, said thickening organic polymers being associative or nonassociative, anionic, cationic, amphoteric or nonionic polymers.

12. The composition of any one of claims 4 to 5, comprising one or more thickening organic polymers, said thickening organic polymers being produced by (co)polymerization of: - Acrylate monomer CH2=C(R')-COOR''' (VIa) and / or - acrylamide monomer CH2=C(R')-CO-N(R") -LY - M (VIb) In equations (VIa) and (VIb): R' and R'' can be the same or different, representing a hydrogen atom or a (C1-C6) alkyl group; R''' represents an alkali metal, an alkaline earth metal, a hydrogen atom, or an alkyl group (C1-C6) optionally substituted with one or more hydroxyl, carboxyl, or amino groups; L represents a straight-chain or branched, saturated or unsaturated, cyclic or acyclic divalent hydrocarbon-based group containing 1 to 20 carbon atoms, optionally inserted or substituted by one or more heteroatoms. Y - represents an anionic group, and M is a cationic counterion, the thickening organic polymer being present in a direct emulsion or in a reverse emulsion.

13. The composition of claim 12, wherein the thickening organic polymer is selected from crosslinked or non-crosslinked acrylic copolymers or methacrylic acid copolymers, either alone or as mixtures, crosslinked or non-crosslinked 2-acrylamido-2-methylpropanesulfonic acid homopolymers and their crosslinked or non-crosslinked acrylamide copolymers, ammonium acrylate homopolymers, or copolymers of ammonium acrylate and acrylamide.

14. The composition of any one of claims 4 to 5, comprising one or more thickening organic polymers having sugar units derived from the following sugars: glucose; galactose; arabinose; rhamnose; mannose; xylose; fucose; dehydrated galactose; galacturonic acid; glucuronic acid; mannuronic acid; galactose sulfate; dehydrated galactose sulfate; and fructose.

15. The composition of any one of claims 4 to 5, comprising one or more thickening organic polymers, wherein the content of the thickening organic polymers ranges from 0.01% by weight to 10% by weight relative to the total weight of the composition.

16. The composition of any one of claims 4 to 5, comprising one or more fatty substances as defined in claim 9 and one or more surfactants as defined in claim 6, wherein the fatty substance / surfactant weight ratio is 5 to 20, including the extreme values.

17. The composition of any one of claims 4 to 5, comprising one or more fatty substances as defined in claim 9, one or more surfactants as defined in claim 6, and one or more thickening organic polymers as defined in claim 11, wherein the weight ratio of the fatty substance / surfactant and polymer is from 0.8 to 10, including the end value.

18. The composition according to any one of claims 4 to 5, comprising an aqueous phase and an organic or oil phase; the composition is an oil-in-water (O / W) type direct emulsion.

19. The composition of any one of claims 4 to 5, comprising one or more organic solvents selected from a) C2-C6 alkanols; b) polyols miscible with water at room temperature (25°C); c) polyol ethers; and d) aromatic alcohols, and mixtures thereof.

20. The composition of any one of claims 4 to 5, comprising one or more organic solvents, said organic solvents being present in an amount of 0.1% to 40% by weight relative to the total weight of said composition, including the end value.

21. The composition of any one of claims 4 to 5, wherein it does not contain any cationic surfactant.

22. A non-therapeutic cosmetic treatment method for caring for and / or applying and / or cleansing keratin materials, the method comprising applying to the keratin material a composition as described in any one of claims 4 to 21.

23. A method for preserving a composition comprising a physiologically acceptable medium, characterized in that, The method includes incorporating the composition with a mixture as defined in any one of claims 1 to 3 or a composition as described in any one of claims 4 to 21.

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