Aqueous composition based on a sennoside and carbonyl alcohol

An aqueous composition combining sennoside A with D-panthenol and citric acid in water overcomes the solubility challenges of sennosides, allowing for the formulation of stable and effective cosmetic products for topical application.

FR3157149A1Active Publication Date: 2025-06-27LOREAL SA
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Patent Information

Application Number
FR2023014834
Authority / Receiving Office
FR · FR
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-12-21
Publication Date
2025-06-27
Estimated Expiration
2043-12-21

AI Technical Summary

Technical Problem

Sennosides, such as sennoside A, are insoluble in water and common cosmetically acceptable solvents, making it difficult to formulate stable cosmetic compositions for topical application.

Method used

An aqueous composition comprising sennoside A, D-panthenol, citric acid, and water, which solubilizes sennoside A and allows for stable formulation in a wide range of cosmetic carriers.

Benefits of technology

The composition effectively solubilizes sennoside A in an aqueous medium, enabling the creation of stable and applicable cosmetic products for skin and mucous membrane care.

✦ Generated by Eureka AI based on patent content.
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Abstract

Aqueous composition based on a sennoside and carbonyl alcohol The present invention relates to a cosmetic composition comprising: at least one compound of formula (I) as defined below, or one of its optical isomers, cis-trans isomers, tautomers or one of its salts, in particular of organic or mineral base or solvates such as hydrates, at least one carbonyl alcohol of formula (II), at least one organic or mineral acid, and water. Figure for the abstract: none
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Description

Title of the invention: Aqueous composition based on a sennoside and carbonyl alcohol

[0001] The present invention relates to a cosmetic composition comprising: a. at least one compound of formula (I) as defined below, or one of its optical isomers, cis-trans isomers, tautomers or one of its salts, in particular of organic or mineral base or solvated such as hydrates, b. at least one carbonyl alcohol of formula (II), c. at least one organic or mineral acid, and d. water.

[0002] Human skin is made up of two compartments, namely a deep compartment, the dermis, and a superficial compartment, the epidermis. The epidermis is in contact with the external environment, and its role is in particular to protect the body from dehydration and from external, chemical or mechanical attacks.

[0003] There is always a need for new cosmetic compositions having interesting properties, particularly on the skin.

[0004] Sennosides can be interesting active ingredients for this purpose. Indeed, this type of active ingredient is known in cosmetics, for example from application JP2002-255733.

[0005] However, sennosides are partially soluble in certain solvents such as methanol or acetone (which are not cosmetically acceptable solvents), and are not soluble in water, particularly at room temperature. They therefore do not allow, as such, the formulation of stable cosmetic compositions applicable to the skin.

[0006] The formulator is therefore looking for compositions comprising a sennoside such as sennoside A which are stable and applicable in particular topically (i.e. on the skin and / or mucous membranes).

[0007] Such compositions must further comprise a certain amount of water, in order to be able to formulate a sennoside, such as sennoside A, in a wide range of cosmetic carriers including lotions, gels or emulsions.

[0008] In this context, the inventors have surprisingly discovered that particular hydrophilic solvents allow the solubilization of a sennoside such as sennoside A, and are compatible with a formulation in an aqueous medium.

[0009] The invention therefore aims to provide a cosmetic composition which responds to all these problems.

[0010] Indeed, as demonstrated in examples, the Applicant has discovered in a manner Surprisingly, sennoside A, although insoluble in water, glycols or various oils, is soluble from 0.5% by weight in an aqueous mixture comprising D-panthenol and citric acid.

[0011] Thus, the present invention relates to a cosmetic composition comprising:

[0012] (a) at least one compound of formula (I) or one of its optical isomers, isomers cis-trans, tautomers or one of its salts, in particular of organic or mineral base or its solvates such as hydrates,

[0013] (b) at least one carbonyl alcohol of formula (II),

[0014] (c) at least one organic or mineral acid, preferably at least one acid organic, preferably at least one (poly)(hydroxy) (C1-C6) alkyl (poly)carboxylic acid, preferably at least one C1-C4 hydroxy (poly)carboxylic acid, preferably at least one alpha hydroxy acid, preferably citric acid, and

[0015] (d) water.

[0016] Preferably, the present invention relates to a cosmetic composition consisting of: a. at least one compound of formula (I) or one of its optical isomers, cis-trans isomers, tautomers or one of its salts, in particular of organic or mineral base or its solvates such as hydrates, b. at least one carbonyl alcohol of formula (II), c. at least one organic or mineral acid, preferably at least one acid organic, preferably at least one (poly)(hydroxy) (C1-C6) alkyl (poly)carboxylic acid, preferably at least one C1-C4 hydroxy (poly)carboxylic acid, preferably at least one alpha hydroxy acid, preferably citric acid, and d. water.

[0017] For the purposes of the present invention, and unless otherwise indicated: - an “alkyl” radical is a saturated, linear or branched hydrocarbon radical, in particular C1-C6, preferably C1-C4; - a “(poly)(hydroxy) (C1-C6) alkyl” radical denotes a C1-C6 alkyl radical, preferably C1-C4, optionally substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3; - a "sugar" radical is a monosaccharide or disaccharide radical. Examples of sugar radicals include: sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose; - by "monosaccharide" is meant a monosaccharide sugar comprising at least 5 carbon atoms of formula CX(H2O)X, with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x = 6. They may be of D or L configuration, and of alpha or beta anomer, as well as one of their salts or their solvates such as hydrates; - by "disaccharide" is meant a di-osidic sugar which is a compound consisting of two oses linked together by O-osidic bonds, said compounds being composed of two monosaccharides (also called mono-osidics) as defined above, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the mono-osidic units are linked together in 1,4 or 1,6 in anomer α (alpha) or [3 (beta), each osidic unit being able to be of L or D configuration, as well as one of its salts or its solvates such as hydrates. A disaccharide is more particularly a polymer formed from two oses (or monosaccharides) having the general formula: -[Cx(H2O)y)]2- or -[(CH2O)x]2-, with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x = 6, and y is an integer which represents x - 1; - by “organic or mineral base salt” we mean a salt of a base or alkaline agent such as alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, ammonia, amines, alkanolamines or salts of so-called “basic” amino acids such as lysine or arginine; - by “skin” we mean the skin of the face and / or body, the scalp; - by "annexes" we mean eyelashes, eyebrows, nails, and hair, in especially eyelashes and hair; - in what follows, and unless otherwise indicated, the limits of a domain of values ​​are included in this domain, in particular in the expressions “between” and “ranging from ... to ..."; - furthermore, the expression “at least one” used in this description is equivalent to the expression “one or more”.

[0018] The invention also relates to a method for caring for the skin and / or mucous membranes comprising the application of the composition according to the invention to the skin and / or mucous membranes.

[0019] The invention also relates to the use of a composition according to the invention for the care of the skin and / or mucous membranes.

[0020] The invention also relates to a final cosmetic composition comprising, in a cosmetically acceptable medium, at least 50% by weight, preferably of 60% to 99% by weight, more preferably from 70 to 95% by weight relative to the total weight of the composition of a composition as described above (i.e. comprising ingredients a) to d)). This final composition corresponds in particular to the final commercialized cosmetic product. Compound of formula (I) (compound (a))

[0021] The composition according to the invention comprises at least one compound of formula (I) or one of its optical isomers, cis-trans isomers (such as an alpha or beta anomer), tautomers or one of its salts, in particular of organic or mineral base, or one of its solvates such as hydrates:

[0022] [Chem.l]

[0023] in which:

[0024] - R' and R' ' are identical or different, preferably identical, and represent a H or a monosaccharide or a polysaccharide comprising up to 20 sugar units, preferably up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide possibly being substituted by a hydroxyl group which must be free, and optionally one or more amine function(s) which may be protected and said monosaccharide or polysaccharide being optionally substituted on its -CH2OH group by a -C(O)-CO2 H group;

[0025] - R represents H or -C-(O)-O-Ri or -Alk-X-Rl, preferably -C-(O)-O-Ri or Alk- O-Ri,

[0026] with X being O, S or -NRi, preferably O; RI being H or a saturated or unsaturated hydrocarbon chain, preferably saturated in C1-C6, more preferably RI corresponds to H, and Alk corresponds to a C1-C6 alkylene group, preferably -CH2-,

[0027] Advantageously, R' and R” are identical or different and represent a monosaccharide or a polysaccharide containing up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide having at least one hydroxyl function which is obligatorily free and / or optionally one or more amine functions which are obligatorily protected.

[0028] Advantageously, the monosaccharide is chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine and N-acetyl-D-galactosamine. The monosaccharide advantageously denotes D-glucose, L-rhamnose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and more preferably D-glucose.

[0029] Advantageously, the polysaccharide containing up to 6 sugar units is chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid chosen from D-iduronic acid or D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-glucosamine, a disaccharide combining L-rhamnose and D-galactose, an oligosaccharide containing at least one xylose which may be advantageously chosen from xylobiose, methyl-[3-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose which is composed of two xylose molecules linked by a 1-4 bond.

[0030] More preferably, R' and R' ' are identical and represent a monosaccharide chosen from D-glucose, D-xylose, L-fucose, L-rhamnose, D-galactose and D-maltose, preferably D-glucose.

[0031] The monosaccharide or polysaccharide of R' and / or R” may be substituted on one or more hydroxymethyl residue(s) by a -C(O)-COOH group.

[0032] Preferably, the compound of formula (I) or one of its optical isomers, cis-trans isomers (such as an alpha or beta anomer), tautomers or one of its salts, in particular of organic or mineral base or one of its solvates such as hydrates, is chosen from sennosides A, B, C, D, E and F, preferentially it is chosen from sennosides A and B, even more preferentially the compound of formula (I) is sennoside A or one of its salts.

[0033] The compound of formula (I) or one of its optical isomers, cis-trans isomers (such as an alpha or beta anomer), tautomers or one of its salts, in particular of organic or mineral base or one of its solvates such as hydrates, preferably sennoside A or one of its salts, is present in solubilized form in the composition. By "in solubilized form" is meant that said compound does not form crystals visible to the naked eye in the composition.

[0034] Sennoside A (C42H38O20) (or acid (9R)-9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(h ydroxymethyl)oxan-2-yl]oxy-9H-anthraen-9-yl]-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6 R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid (IUP AC name) is the chemical compound of formula (I') below:

[0035] [Chem.2] 0^ (D

[0036] Its CAS number is 81-27-6. It is a derivative of anthraquinone, found in plants of the genus Senna. It typically appears as a very hygroscopic yellow powder.

[0037] Sennoside A has 4 pKa, whose values ​​are pKal = 3.3, pKa2 = 3.9, pKa3 = 7.5 and its last pKa (pKa4) is equal to 8.2.

[0038] The compound of formula (I), preferably sennoside A, may also be in salt form. By "salt" is meant a cosmetically acceptable salt, i.e. compatible with application to the skin, mucous membranes and / or appendages. The salt of the compound of formula (I), preferably the salt of sennoside A, may be an alkali or alkaline earth metal salt, preferably a calcium, magnesium, sodium or potassium salt.

[0039] Typically, the salt of the compound of formula (I), preferably the sennoside salt such as sennoside A salt, may exist once the compound is introduced into the composition. Indeed, the compound of formula (I) is introduced in non-salified form into the composition.

[0040] Sennoside A is for example marketed by INTERCHIM under the name Sennoside A.

[0041] Preferably, the composition comprises between 0.1 and 5% by weight of the compound of formula (I) or one of its optical isomers, cis-trans isomers (such as an alpha or beta anomer), tautomers or one of its salts, in particular of organic or mineral base or one of its solvates such as hydrates, relative to the total weight of the composition, preferably between 0.2 and 4% by weight, preferably between 0.3 and 3% by weight, preferably between 0.4 and 1% by weight.

[0042] Preferably, the composition comprises between 0.1 and 5% by weight of sennoside A or one of its salts relative to the total weight of the composition, preferably between 0.2 and 4% by weight, preferably between 0.3 and 3% by weight, preferably between 0.4 and 1% by weight. Carbonyl alcohol of formula (II) (compound (b))

[0043] The composition according to the invention comprises at least one carbonyl alcohol of formula (II):

[0044] [Chem 3]

[0045] (HO)n-Alk-Y-Alk'-(Z)p (II)

[0046] in which Alk denotes a linear or branched, substituted or unsubstituted, preferably branched, alkylene group which comprises from 1 to 8 carbon atoms, particularly from 2 to 6 carbon atoms, more particularly 3 to 5 carbon atoms, and Alk can be substituted by at least one -OH radical;

[0047] Alk' denotes a linear alkylene group comprising from 1 to 6 carbon atoms, particularly 2 to 4 carbon atoms;

[0048] Y corresponds to a carbonyl group -C(O)-, a group -C(O)O- or a group -C(O)-NH-, preferably a group -C(O)-NH-; and

[0049] Z denotes -OH or -COOH, preferably -OH;

[0050] n is an integer ranging from 1 to 4, preferably 1 or 2;

[0051] p is an integer equal to 1 or 2, preferably equal to 1.

[0052] Preferably, the compound of formula (II) is such that n=p=l; Z = -OH; Alk is a branched alkylene group comprising from 3 to 5 carbon atoms and substituted by an -OH radical; Y = -C(O)-NH-; and Alk' is a linear alkylene group comprising from 2 to 4 carbon atoms.

[0053] Preferably, the compound of formula (II) is D-panthenol. Thus, preferably, the composition according to the invention comprises at least D-panthenol.

[0054] D-panthenol (or enantiomer (2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide, also called dexpanthenol) is the chemical compound of the following formula (II'):

[0055] [Chem.4] (II')

[0056] Its CAS number is 81-13-0. It is an alcohol analogue of panthothenic acid (vitamin B5), and is therefore a provitamin B5. In the body, it is rapidly oxidized to pantothenic acid.

[0057] It is a transparent viscous liquid at room temperature.

[0058] The composition according to the invention may comprise only D-panthenol, or else panthenol in racemic form, i.e. comprising the (R) (or D) and (S) (or L) enantiomers.

[0059] D-panthenol is, for example, marketed as a mixture in water and citric acid. Such a mixture is marketed in particular by BASF under the name D-Panthenol 75 W.

[0060] Preferably, the composition comprises between 10% and 90% by weight of carbonyl alcohol of formula (II) relative to the total weight of the composition, preferably between 30% and 85% by weight, preferably between 50 and 80% by weight, preferably between 60% and 75% by weight.

[0061] Preferably, the composition comprises between 10% and 90% by weight of D-panthenol relative to the total weight of the composition, preferably between 30% and 85% by weight, preferably between 50 and 80% by weight, preferably between 60% and 75% by weight.

[0062] Preferably, the composition according to the invention has a weight ratio (compound of formula (I): carbonyl alcohol of formula (II)) of between 0.1-1: 70-80. Preferably, the composition according to the invention has a weight ratio (compound of formula (I): carbonyl alcohol of formula (II) of between 0.4-0.6: 72-76.

[0063] Preferably, the composition according to the invention has a weight ratio (sennoside A or one of its salts: D-panthenol) of between 0.1-1: 70-80. Preferably, the composition according to the invention has a weight ratio (sennoside A or one of its salts: D-panthenol) of between 0.4-0.6: 72-76. Organic or mineral acid (compound (c))

[0064] The composition according to the invention comprises at least one organic or mineral acid.

[0065] Of course, the organic or mineral acid (c) is different from the carbonyl alcohol of formula (II) (b).

[0066] Preferably, the composition according to the invention comprises at least one organic acid. Preferably, the acid is a (poly)(hydroxy) (C1-C6) alkyl (poly)carboxylic acid. Preferably, the acid is a C1-C4 hydroxy (poly)carboxylic acid, preferably at least one alpha hydroxy acid (AHA).

[0067] By alpha hydroxy acid is meant according to the present invention a carboxylic acid having at least one hydroxy function (-OH) occupying an alpha position on said acid (carbon adjacent to a carboxylic acid function). This acid can be present in the final composition in the form of free acid and / or in the form of one of its associated salts (salts with an organic base or an alkali in particular).

[0068] The α-hydroxy acids (alpha hydroxy acids or AHAs) are for example chosen from citric acid, lactic acid, methyllactic acid, glucuronic acid, glycolic acid, pyruvic acid, 2-hydroxybutanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, 2-hydroxynonanoic acid, 2-hydroxydecanoic acid, 2-hydroxyundecanoic acid, acid 2-hydroxydodecanoic acid, 2-hydroxytetradecanoic acid, 2-hydroxyhexadecanoic acid, 2-hydroxyoctadecanoic acid, 2-hydroxytetracosanoic acid, 2-hydroxyeicosanoic acid, mandelic acid, phenyllactic acid, gluconic acid, galacturonic acid, aleuritic acid, ribonic acid, tartronic acid, tartaric acid, malic acid, fumaric acid, their salts and mixtures thereof.

[0069] According to a preferred embodiment, the alpha hydroxy acid is chosen from citric acid, lactic acid, malic acid, tartaric acid and their salts. More particularly, the alpha hydroxy acid is chosen from citric acid, lactic acid, their salts and their mixtures.

[0070] Preferably, the alpha hydroxy acid is citric acid.

[0071] Preferably, the composition comprises between 0.01% and 3% by weight of organic or mineral acid, preferably organic acid, relative to the total weight of the composition, preferably between 0.1% and 2% by weight, preferably between 0.5% and 1% by weight.

[0072] Preferably, the composition comprises between 0.01% and 3% by weight of AHA, preferably citric acid, relative to the total weight of the composition, preferably between 0.1% and 2% by weight, preferably between 0.5% and 1% by weight. Water (compound (d))

[0073] The composition according to the invention comprises water.

[0074] The water used may be sterile demineralized water and / or a floral water such as rose water, cornflower water, chamomile water or linden water, and / or a natural thermal or mineral water such as VITTEL water, LUCAS water or LA ROCHE POSAY water.

[0075] The composition preferably comprises at least 5% by weight of water relative to the total weight of the composition, preferably at least 10% by weight, preferably at least 15% by weight, preferably at least 20% by weight.

[0076] The composition preferably comprises less than 50% by weight of water relative to the total weight of the composition, preferably less than 40% by weight, preferably less than 30% by weight.

[0077] Preferably, the composition according to the invention has a pH lower than the 4th pKa of the compound of formula (I), preferably lower than the 3rd pKa of the compound of formula (I). Preferably, the pH of the composition according to the invention is between 5.0 and 7.0, preferably between 6.0 and 7.0.

[0078] Indeed, in the present case, sennoside A is insoluble in water at its native pH, i.e. around 4.3. It is known that by raising the pH of a molecule beyond its last pKa, it becomes soluble. However, since sennoside A has 4 pKa and its last pKa is equal to 8.2, such a pH results in the formulation of sennoside A beyond 8.3, which is incompatible with topical cosmetic application, in particular on the skin and / or mucous membranes. Indeed, topical cosmetic compositions, in particular applicable to the skin and / or mucous membranes, must have an acceptable physiological pH, i.e. between 5.0 and 7.0.

[0079] Preferably, the composition according to the invention has a pH of less than 8.3, preferably less than 7.0.

[0080] Preferably, the present invention relates to a cosmetic composition comprising: a. sennoside A or one of its salts, b. at least D-panthenol, c. citric acid, and d. water.

[0081] Preferably, the present invention relates to a cosmetic composition consisting of: a. sennoside A or one of its salts, b. at least D-panthenol, c. citric acid, and d. water.

[0082] The composition according to the invention may also contain ingredients usual in the cosmetic field, such as preservatives, perfumes, fillers, oils, waxes, pasty fatty substances, sun protection filters or UV filters, odor absorbers, coloring materials, basic agents, sequestering agents or active ingredients.

[0083] The quantities of these different ingredients are those conventionally used in the field considered, and for example from 0.01 to 20% of the total weight of the composition. These ingredients, depending on their nature, can be introduced into the fatty phase and / or into the aqueous phase.

[0084] Of course, those skilled in the art will take care to choose the possible compound(s) to be added to the composition according to the invention and their quantities in such a way that the advantageous properties intrinsically attached to the composition in accordance with the invention are not, or not substantially, altered by the envisaged addition.

[0085] The composition in accordance with the invention can be obtained in a conventional manner by a person skilled in the art.

[0086] The invention also relates to a final cosmetic composition comprising, in a cosmetically acceptable medium, at least 50% by weight relative to the total weight of the composition of a composition as described above (i.e. comprising ingredients a) to d)), preferably from 60 to 99% by weight, more preferably from 70 to 95% by weight relative to the total weight of the composition. The final composition corresponds in particular to the final commercialized cosmetic product, based on sennoside. By cosmetically acceptable medium is meant a medium compatible with the skin and / or its appendages.

[0087] The invention also relates to a method for caring for the skin and / or mucous membranes comprising the application of the composition according to the invention or of the final composition according to the invention to the skin and / or mucous membranes.

[0088] The invention also relates to the use of a composition according to the invention or of a final composition according to the invention for the care of the skin and / or mucous membranes.

[0089] The following examples will allow a better understanding of the invention, without however being limiting in nature. The raw materials are named by their chemical or INCI name. The quantities indicated are in % by weight of raw materials relative to the total weight of the composition (% w / w), unless otherwise stated. Examples

[0090] Example 1: Preparation of compositions according to the invention and evaluation with respect to comparative compositions

[0091] Two compositions according to the invention are compared with 3 counter-examples. Operating mode

[0092] The compositions according to the invention of Table 1 below are prepared as follows:

[0093] Sennoside A at 0.5% by weight is added to the mixture of panthenol, water and citric acid, sold in liquid form, then the mixture is put under magnetic stirring.

[0094] In the case of counter-example 1 and of the example according to the invention (ii):

[0095] Panthenol (pure, i.e. 100% by weight of active ingredient relative to the weight of ingredient) is very sticky and thick; it is dissolved in water first, then sennoside A at 0.5% by weight is sprinkled into the beaker with the aqueous solution of panthenol under magnetic stirring.

[0096] [Tables 1] Ingredients (% w / w) Example according to the invention (i) Example according to the invention (ii) Counter-example 1 Counter-example 2 Counter-example 3 Sennoside A 0.5 0.5 0.5 0.5 0.5 Panthenol* - 74.5 70 99.5 - Panthenol** 99.5 - - - - Water - Qsp 100 Qsp 100 - Qsp 100 Citric acid monohydrate; marketed by TTCA - 1 - - - Observation Soluble Soluble Insoluble Mixing impossible because the raw material is too viscous and sticky Insoluble

[0097] *Panthenol: D-Panthenol Care from BASF, 100% by weight of active ingredient relative to the total weight of ingredient

[0098] **Panthenol: D-Panthenol 75 IV from BASF, which is a mixture, by weight of active ingredient relative to the total weight of ingredient, of 74.5% D-panthenol, 24.5% water and 1% citric acid

[0099] The results show that sennoside A is insoluble in water. However, by adding D-panthenol in solution at 75% by weight of active ingredient, sennoside A becomes soluble. Conclusion

[0100] Surprisingly, sennoside A is soluble in D-panthenol mixed with water and citric acid. The compositions according to the invention remain stable even after storage for 2 months at room temperature.

Claims

1. Claims Cosmetic composition comprising: (a) at least one compound of formula (I) or one of its optical isomers, cis-trans isomers, tautomers or one of its salts, in particular of organic or mineral base or its solvates such as hydrates: [Chem.l] (I) in which: - R' and R' ' are identical or different, preferably identical, and represent an H or a monosaccharide or a polysaccharide comprising up to 20 sugar units, preferably up to 6 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide possibly being substituted by a hydroxyl group which must be free, and optionally one or more amine function(s) which may be protected and said monosaccharide or polysaccharide being optionally substituted on its -CH2OH group by a -C(O)-CO2H group; - R represents H or -C-(O)-O-Ri or -Alk-X-Rl, preferably -C-(O)-OR! or Alk-O-Rj, with X being O, S or -NRb, preferably O; RI being H or a saturated or unsaturated hydrocarbon chain, preferably saturated in C1-C6, more preferably RI corresponds to H, and Alk corresponds to a C1-C6 alkylene group, preferably -CH2-, (b) at least one carbonyl alcohol of formula (II): [Chem 3] (HO)n-Alk-Y-Alk'-(Z)p (II) in which Alk denotes a linear or branched alkylene group, preferably branched, which comprises from 1 to 8 carbon atoms, particularly from 2 to 6 carbon atoms, more particularly 3 to 5 carbon atoms, and Alk may be substituted by at least one -OH radical; Alk' denotes a linear alkylene group comprising from 1 to 6 carbon atoms, particularly 2 to 4 carbon atoms; Y corresponds to a carbonyl group -C(O)-, a -C(O)O- group, or a -C(O)-NH- group, preferably a -C(O)-NH- group; and Z denotes -OH or -COOH, preferably -OH; n is an integer ranging from 1 to 4, preferably 1 or 2; p is an integer equal to 1 or 2, preferably equal to 1, (c) at least one organic or mineral acid, and (d) water.

2. Composition according to claim 1, wherein the compound of formula (I) is such that R' and R' ' are identical and represent a monosaccharide chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine and N-acetyl-D-galactosamine, preferably chosen from D-glucose, L-rhamnose, D-xylose, N-acetyl-D-glucosamine and L-fucose, and more preferably D-glucose; preferably the compound of formula (I) or one of its optical isomers, cis-trans isomers, tautomers or one of its salts, in particular of organic or mineral base or one of its solvates such as hydrates, is chosen from sennosides A, B, C, D, E and F, preferentially it is chosen from sennosides A and B.

3. Composition according to one of the preceding claims, in which the compound of formula (I) is sennoside A or one of its salts.

4. Composition according to one of the preceding claims, in which the carbonyl alcohol of formula (II) is such that n=p=l; Z = -OH; Alk is a branched alkylene group comprising from 3 to 5 carbon atoms and substituted by an -OH radical; Y = -C(O)-NH-; and Alk' is a linear alkylene group comprising from 2 to 4 carbon atoms.

5. Composition according to one of the preceding claims, in which the carbonyl alcohol of formula (II) is D-panthenol.

6. Composition according to one of the preceding claims, which comprises between 0.1 and 10% by weight of compound of formula (I) relative to the total weight of the composition, preferably between 0.2 and 5% by weight, preferably between 0.3 and 3% by weight, preferably between 0.4 and 1% by weight.

7. Composition according to one of the preceding claims, which comprises between 10% and 90% by weight of carbonyl alcohol of formula (II) relative to the total weight of the composition, preferably between 30% and 85% by weight, preferably between 50 and 80% by weight, preferably between 60% and 75% by weight.

8. Composition according to one of the preceding claims, which has a weight ratio (compound of formula (I): carbonyl alcohol of formula (II)) of between 0.1-1: 70-80, preferably a weight ratio (compound of formula (I): carbonyl alcohol of formula (II)) of between 0.4-0.6: 72-76.

9. Composition according to one of claims 3 or 5, which has a weight ratio (sennoside A or one of its salts: D-panthenol) of between 0.1-1: 70-80, preferably a weight ratio (sennoside A or one of its salts: D-panthenol) of between 0.4-0.6: 72-76.

10. Composition according to one of the preceding claims, in which the organic or mineral acid is an organic acid, preferably a (poly)(hydroxy) (C1-C6) alkyl (poly)carboxylic acid, preferably a C1-C4 hydroxy (poly)carboxylic acid, preferably an alpha hydroxy acid;preferably the alpha hydroxy acid is chosen from citric acid, lactic acid, methyllactic acid, glucuronic acid, glycolic acid, pyruvic acid, 2-hydroxybutanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, 2-hydroxynonanoic acid, 2-hydroxydecanoic acid, 2-hydroxyundecanoic acid, 2-hydroxydodecanoic acid, 2-hydroxytetradecanoic acid, 2-hydroxyhexadecanoic acid, 2-hydroxyoctadecanoic acid, 2-hydroxytetracosanoic acid, 2-hydroxyeicosanoic acid, mandelic acid, phenyllactic acid, gluconic acid, galacturonic acid, aleuritic acid, ribonic acid, tartronic acid, tartaric acid, malic acid, fumaric acid, their salts and their mixtures; preferably the alpha hydroxy acid is chosen from citric acid, lactic acid, their salts and their mixtures;preferentially the alpha hydroxy acid is citric acid.;

11. Composition according to one of the preceding claims, which comprises between 0.01% and 3% by weight of organic or mineral acid, preferably citric acid, relative to the total weight of the composition, preferably between 0.1% and 2% by weight, preferably between 0.5% and 1% by weight.

12. Composition according to one of the preceding claims, which comprises at least 5% by weight of water relative to the total weight of the composition, preferably at least 10% by weight, preferably at least 15% by weight, preferably at least 20% by weight; and / or less than 50% by weight of water relative to the total weight of the composition, preferably less than 40% by weight, preferably less than 30% by weight.

13. Composition according to one of the preceding claims, which has a pH of less than 8.3, preferably less than 7.0, preferably between 5.0 and 7.0, preferably between 6.0 and 7.

0.

14. Final cosmetic composition comprising, in a cosmetically acceptable medium, at least 50% by weight, preferably from 60 to 99% by weight, more preferably from 70 to 95% by weight relative to the total weight of the composition of a composition according to one of claims 1 to 13.

15. A method of caring for the skin and / or mucous membranes comprising the application of a composition according to one of claims 1 to 13 or 14 to the skin and / or mucous membranes.

16. Use of a composition according to one of claims 1 to 13 or 14 for the care of the skin and / or mucous membranes.

Citation Information

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