Compositions comprising more than 10% by weight of 4-(3-ethoxy-4-hydroxyphenyl) but-2-one derivatives

Abstract

The present invention relates to a composition comprising more than 10% by weight of a 4-(3-ethoxy-4-hydroxyphenyl) but-2-one derivative corresponding to formula (I) described below, at least one substance which is liquid at room temperature and ambient pressure, selected from polar protic organic solvents, and optionally water. The invention also relates to the use of a composition according to the invention for improving the microbial preservation of a cosmetic composition. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a composition comprising more than 10% by weight of a 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one derivative corresponding to formula (I) as described below, at least one substance as defined below that is liquid at room temperature and ambient pressure, and optionally water.

[0002] The invention also relates to the use of a composition according to the invention for improving the microbial preservation of cosmetic compositions. Background Art

[0003] Microorganisms can survive and spread relatively easily in cosmetic, dermatological, pharmaceutical, and food products that do not contain preservatives.

[0004] Therefore, preservatives are regularly added to most industrial preparations intended for storage or preservation in order to prevent microbial growth over time. Microbial contamination is also common during the production of industrial products, even when the starting ingredients of the product are "clean", i.e., free of contaminating microorganisms.

[0005] For example, water, a ubiquitous component of most cosmetic, pharmaceutical, dermatological, or even nutraceutical products, must be free of contaminating microorganisms. Similarly, other ingredients must be screened for the presence of contaminating microorganisms. Cleanliness must be rigorously monitored during the production of these industrial products, the handling of their contents, and the filling of their containers in order to minimize or even eliminate the presence of contaminating microorganisms.

[0006] Despite these precautions, the microbiological integrity of this type of product may require the presence of one or more preservatives that are compatible with the product and the stability of the composition. The product must not allow the growth or viability of contaminating microorganisms.

[0007] Furthermore, maintaining cleanliness during use of such products remains problematic, especially when they are handled, as fingers, applicators (e.g., cosmetic applicators), and even ambient air are not sterile. Therefore, preservatives have proven necessary to reduce microbial contamination during normal use by consumers.

[0008] In general, all products sold (especially cosmetic products) must be free of pathogenic microorganisms (Kirk Othmer Encyclopedia, Cosmetics, Martin M. Rieger, 04 / 12 / 2000). In recent years, preservation problems have also led to the introduction of preservatives with different action profiles in order to combat resistant contaminating microorganisms.

[0009] The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and its derivatives are commonly used as preservatives in compositions, especially cosmetic compositions, due to their favorable properties against various bacterial strains (both Gram-positive and Gram-negative) on fungi and yeasts. The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one also exhibits high activity against bacteria of the Burkholderia cepacia complex.

[0010] The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and its derivatives are usually used alone or as a mixture with other preservative or non-preservative compounds to effectively protect various compositions, especially cosmetic compositions, from microbial contamination during their preparation and during use in daily life.

[0011] The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (also known as ethylgingerone) can be synthesized, for example, according to the following synthetic route ( A ) prepared from ethyl vanillin:

[0012]

[0013] In the synthetic pathway ( A )middle:

[0014] - R2 represents a hydrogen atom and R3 represents a linear (saturated) C1-C6 alkyl group optionally substituted by a hydroxyl group; or a linear C2-C6 alkenyl group (C=C unsaturated), or a linear C2-C12 alkenyl group optionally substituted by a hydroxyl group;

[0015] - or R2 represents methyl or ethyl, and R3 represents a straight-chain (saturated) C1-C6 alkyl group optionally substituted by hydroxy; or a straight-chain C2-C6 alkenyl group (C=C unsaturated), or a straight-chain C2-C12 alkenyl group optionally substituted by hydroxy.

[0016] However, once synthesized, ethylgingerone and its derivatives generally have the disadvantage of not being sufficiently stable in various compositions, since the latter may crystallize at temperatures that may vary from 15°C to 40°C.

[0017] Therefore, despite their advantageous antimicrobial properties, their use may prove to be limited during the relatively long periods of time following their preparation and during their formulation in cosmetic, pharmaceutical, dermatological or nutraceutical compositions, in particular cosmetic compositions, or during their transport and / or storage prior to their use as antimicrobial agent in such compositions.

[0018] Therefore, these crystallization risks may also hinder the antimicrobial efficacy of these derivatives, especially in cosmetic applications.

[0019] Furthermore, during the industrial-scale production of compositions, in particular cosmetic compositions, comprising the compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and its derivatives of formula (I) or (I') as described below, it was found that the compounds of formula (I) and in particular (I') are difficult to handle during the manufacturing and formulation processes due to their tendency to recrystallize in the pipes and other access devices of the industrial reactors. In addition to the problems of clogging, subsequent cleaning and loss of the amount of the compound of formula (I) and in particular (I'), the amount actually present in the composition, in particular the cosmetic composition, is ultimately altered, which becomes difficult to manage in terms of quality during large-scale production and creates difficulties in terms of reproducibility.

[0020] In other words, recrystallization of compounds of formula (I), in particular formula (I'), during their manufacture, transport, storage, handling and / or formulation has a great influence on the final amount of compound actually present in a composition, in particular a cosmetic composition.

[0021] It is therefore of great interest to be able to produce commercial products comprising at least ethylgingerone and its derivatives of formula (I) or (I'), which can be processed and for which it is possible to predict with greater certainty - when it is necessary to add the compound of formula (I) or (I') in large quantities to a composition comprising other, in particular cosmetic ingredients and active agents and in particular on an industrial scale - the amount that will ultimately be present in said product.

[0022] Therefore, there is a real need to provide a composition comprising the compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and / or one of its derivatives which does not exhibit the above-mentioned disadvantages, i.e. a composition in which such compounds are stable, in particular at temperatures that can range from 15°C to 40°C and in particular from 20°C to 40°C. Summary of the Invention

[0023] In other words, one of the objects of the present invention is to provide a composition that is stable, in particular at temperatures that can range from 15°C to 40°C and in particular from 20°C to 40°C, wherein the risk of crystallization of the compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and its derivatives is minimized or the crystallization is significantly slowed down.

[0024] The technical problem has been solved by using a composition for the preparation of a cosmetic or pharmaceutical product, comprising i) one or more 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one derivatives of formula (I) or (I') as defined below in an amount of more than 10% by weight; and one or more 5Pa). Preferably, the liquid substance is selected from (non-)polar (non-)protic solvents, more preferably from polar protic solvents. Preferably, the liquid substance is selected from (non-)polar (non-)protic organic solvents, more preferably from polar protic organic solvents.

[0025] In particular, the present invention relates to a composition comprising i) one or more compounds of formula (I) as defined below, and also one of its optical or geometric isomers, and / or one of its salts with an organic or inorganic acid or base, and / or one of its solvates, such as a hydrate; ii) one or more substances that are liquid at room temperature and atmospheric pressure; iii) optionally water.

[0026] According to a preferred embodiment, the one or more substances that are liquid at room temperature and atmospheric pressure are selected from polar protic organic solvents.

[0027] More particularly, a subject of the present invention is, among other things, a composition comprising i) one or more compounds of the following formula (I):

[0028]

[0029] In formula (I):

[0030] -R 1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 6 carbon atoms;

[0031] -R 2 represents a hydrogen atom or a C2-C4 alkyl group such as a methyl or ethyl group;

[0032] -R 3 represents a linear or branched, saturated or unsaturated hydrocarbon group containing 1 to 12 atoms, which is optionally substituted by an aryl group; the aryl group is preferably a phenyl group which is optionally substituted by one or more groups selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy and combinations thereof;

[0033] and also one of its optical isomers or geometric isomers, and / or one of its salts with an organic or inorganic acid or base, and / or one of its solvates, such as a hydrate;

[0034] -ii) at least one polar protic organic solvent, and

[0035] -iii) optionally water;

[0036] It is understood that i) said compound of formula (I) is present in a content greater than 10% by weight relative to the total weight of the composition.

[0037] The composition according to the invention thus makes it possible to achieve the object described above, namely that the compound of formula (I) is stable, in particular does not crystallize, at temperatures that may vary from 15°C to 40°C and in particular from 20°C to 40°C, and this for a period of time that may range from a few days to several months.

[0038] In other words, the composition according to the invention makes it possible to stabilize at least one compound of formula (I) at the end of its preparation, by in particular reducing at least the risk of recrystallization, and during its transport and / or storage, as well as its use in the production of commercial products, for use as antimicrobial agent in various applications, including cosmetic applications.

[0039] Thus, the compositions according to the invention can advantageously be stored, used in production plants and / or transported for relatively long periods of time at temperatures that may range from 15°C to 40°C and in particular from 20°C to 40°C, while reducing the risk of crystallization of the compound of formula (I).

[0040] Advantageously, the composition according to the invention can be stored, used in production plants and / or transported for relatively long periods of time at temperatures that may range from 15°C to 40°C and in particular from 20°C to 40°C, without the compound of formula (I) crystallizing.

[0041] In other words, the composition according to the invention makes it possible to minimize the risk of crystallization of the compound of formula (I) or (I') or to significantly slow down its crystallization, thus ensuring its effective use as antimicrobial agent in various applications, in particular in cosmetic applications.

[0042] In yet other words, the composition according to the invention has the advantage of slowing down the crystallization kinetics of at least one compound of formula (I) or (I').

[0043] Therefore, a subject of the present invention is also the use of a composition according to the invention for improving the stability of a compound of formula (I) or (I′), in particular at temperatures ranging from 15°C to 40°C, and in particular from 20°C to 40°C, preferably for slowing down the recrystallization of a compound of formula (I) or (I′) at temperatures ranging from 15°C to 40°C, and in particular from 20°C to 40°C.

[0044] A subject of the present invention is likewise the use of said composition for improving the microbial preservation of cosmetic compositions.

[0045] Another subject of the present invention is a process for manufacturing a commercial or industrial product using one or more compounds of formula (I) or (I'), comprising the step of adding a composition according to the invention to said manufacturing process.

[0046] It appears that the recrystallization step slows down the manufacturing process, and in particular the steps added to the process, by several minutes to several days, at the same temperature and atmospheric pressure, and prevents the formation of impurities of the product and various liquid substances, in particular the solvent.

[0047] Other subjects, features, aspects and advantages of the present invention will become still more clearly apparent upon reading the following description and examples.

[0048] In the following text and unless otherwise indicated, the limits of the range of values ​​are included in the range, especially in the expressions "between" and "ranging from to".

[0049] In addition, the expression "at least one" used in this specification is equivalent to the expression "one or more".

[0050] Furthermore, the expression "at least" as used in this description is equivalent to the expression "greater than or equal to". Finally, in a manner known per se, the term "C n ” or “Cn” compound or group indicates a compound or group containing “n” carbon atoms in its chemical structure.

[0051] Within the meaning of the present invention, the terms "alkaline agent" and "alkalinizing agent" are used indiscriminately.

[0052] The alkalizing agent may be an inorganic alkali agent, preferably selected from the group consisting of alkali metal hydroxides or alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, alkali metal carbonates or alkaline earth metal carbonates, such as sodium carbonate or potassium carbonate, and mixtures thereof. The alkalizing agent may be an organic alkali agent, preferably selected from the group consisting of mono(C1-C6) (hydroxy) alkylamines, di(C1-C6) (hydroxy) alkylamines, tri(C1-C6) (hydroxy) alkylamines (preferably tri(C1-C6) (hydroxy) alkylamines), saturated or unsaturated cyclic amines, which are aromatic, such as pyridine, or non-aromatic, optionally substituted with one or more (C1-C4) alkyl groups, such as tetrahydropyridine, optionally substituted with one or more (C1-C4) alkyl groups, piperidine, optionally substituted with one or more (C1-C4) alkyl groups, or piperazine, optionally substituted with one or more (C1-C4) alkyl groups. Preferably, the alkalizing agent of the present invention is a tertiary amine.

[0053] Preferably, the alkalizing agent is selected from the group consisting of alkali metal hydroxides or alkaline earth metal hydroxides, in particular sodium hydroxide, alkali metal (bi)carbonates or alkaline earth metal (bi)carbonates, in particular sodium (bi)carbonate or potassium (bi)carbonate, and tri(C1-C6) (hydroxy)alkylamines, in particular tri(C1-C6)alkylamines, especially triethylamine.

[0054] More preferably, the alkalizing agent is inorganic and selected from the group consisting of alkali metal hydroxides or alkaline earth metal hydroxides, alkali metal (bi)carbonates or alkaline earth metal (bi)carbonates, and mixtures thereof, in particular alkali metal hydroxides or alkaline earth metal hydroxides, in particular sodium hydroxide.

[0055] As indicated above, the composition according to the invention comprises at least one compound of formula (I) in an amount greater than 10% by weight relative to the total weight of said composition.

[0056] Preferably, in formula (I), R 1 represents a straight-chain, saturated or unsaturated hydrocarbon group containing 1 to 6 carbon atoms.

[0057] Preferably, in formula (I), R 1 represents a straight-chain, saturated hydrocarbon group containing 1 to 6 carbon atoms.

[0058] Preferably, in formula (I), R 3 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 12 carbon atoms.

[0059] Preferably, in formula (I), R 2 Represents a hydrogen atom.

[0060] Preferably, in formula (I), R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, and especially a C1 alkyl group.

[0061] Preferably, in formula (I), R 3 represents a linear or branched, preferably linear C1-C6 alkyl group; preferably a linear or branched, preferably linear C1-C4 alkyl group, more preferably a linear or branched, preferably linear C1-C3, especially C1 alkyl group.

[0062] Preferably, in formula (I), R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as ethyl group.

[0063] Advantageously, in formula (I), R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2 Represents a hydrogen atom.

[0064] Advantageously, in formula (I), R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, and especially a C1 alkyl group.

[0065] Advantageously, in formula (I), R 2 represents a hydrogen atom and R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, and especially a C1 alkyl group.

[0066] Advantageously, R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2 Represents a hydrogen atom; R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, and especially a C1 alkyl group.

[0067] Advantageously, R 1 represents a straight-chain C1-C4 alkyl group, more preferably a straight-chain C2-C4 alkyl group such as ethyl; R 2 represents a hydrogen atom; R 3 represents a straight-chain C1-C6 alkyl group; preferably a straight-chain C1-C4, more preferably C1-C3, especially C1 alkyl group.

[0068] Preferably, the compound of formula (I) is a compound corresponding to the following formula (I'):

[0069]

[0070] As indicated, the compound of formula (I) is present in an amount greater than 10% by weight relative to the total weight of the composition according to the invention.

[0071] For the purposes of the present invention, "an amount or content greater than 10% by weight" is understood to mean that the compound of formula (I) or (I') is present in an amount or content strictly greater than 10% by weight relative to the total weight of the composition, that is to say excluding the value of 10% by weight.

[0072] If the composition according to the invention comprises several different compounds of formula (I), "amounts or contents greater than 10% by weight" is understood to mean that the sum by weight of the compounds of formula (I) relative to the total weight of the composition is strictly greater than 10% by weight, that is to say excluding the value of 10% by weight.

[0073] According to a particular embodiment of the present invention, the composition comprises only one compound of formula (I), more preferably a compound of formula (I').

[0074] Preferably, the compound of formula (I) or (I') is present in a content greater than or equal to 20% by weight, more preferably in a content greater than or equal to 30% by weight, even more preferably in a content greater than or equal to 40% by weight, better still in a content greater than or equal to 50% by weight, even better still in a content greater than or equal to 60% by weight, in particular in a content greater than or equal to 70% by weight, more particularly in a content greater than or equal to 80% by weight and especially in a content greater than or equal to 90% by weight relative to the total weight of the composition according to the invention.

[0075] Preferably, the compound of formula (I) or (I') is present in a content ranging from 30% to 99% by weight, more preferably in a content ranging from 50% to 98% by weight, even more preferably in a content ranging from 60% to 97% by weight, better still in a content ranging from 70% to 96% by weight, even better still in a content ranging from 75% to 95% by weight, in particular in a content ranging from 80% to 94% by weight, more particularly in a content ranging from 85% to 93% by weight, such as 90% by weight, relative to the total weight of the composition. Advantageously, the compound of formula (I) or (I') is present in a content ranging from 75% to 95% by weight, in particular in a content ranging from 80% to 94% by weight, more particularly in a content ranging from 85% to 93% by weight, such as 90% by weight, relative to the total weight of the composition.

[0076] According to one embodiment of the present invention, the composition comprises as liquid substance ii) at least one polar protic organic solvent.

[0077] Preferably, the polar protic organic solvent ii) is selected from polyols.

[0078] Preferably, the liquid substance is selected from the group consisting of polar protic organic solvents such as polyols.

[0079] The term "(poly)ol" is understood to mean a polyol at room temperature (25°C) and atmospheric pressure (1.013×10 5 Pa) is a liquid compound, the compound comprising C2 to C 10 , in particular a hydrocarbon chain of C2 to C5, more particularly C3 to C4, such as C3, which is linear or branched, saturated or unsaturated, preferably saturated and contains one or more hydroxyl groups, preferably 2 to 5 hydroxyl groups, more particularly 2 to 3, more preferably 2 hydroxyl groups.

[0080] Preferably, the (poly)alcohol is selected from (C2-C 10 )alkane (poly)ols, more preferably selected from (C2-C6)alkane (poly)ols.

[0081] For the purposes of the present invention, the term "(C2-C 10 )alkane (poly)ols" are understood as meaning linear or branched, preferably straight-chain, alkanes containing 1 to 10 carbon atoms and containing one or more hydroxyl groups (-OH), preferably 2 or 3 hydroxyl groups, more preferably 2 hydroxyl groups.

[0082] In particular, the polar protic organic solvent is a (C2-C6)alkanediol or a (C2-C6)alkanetriol, preferably a (C2-C6)alkanediol. More preferably, the (non-)polar (non-)protic organic solvent is a (C2-C4)alkanediol or a (C2-C4)alkanetriol, preferably a (C2-C4)alkanediol.

[0083] Preferably, the polar protic organic solvent is propylene glycol, in particular selected from the group consisting of propane-1,2-diol (or propylene glycol), propane-1,3-diol, butane-1,3-diol (or butanediol) and mixtures thereof, preferably 1,3-propylene glycol.

[0084] According to a particular embodiment of the present invention, the composition comprises as polar protic organic solvent ii) one or more (C2-C6)alkanols, preferably (C2-C4)alkanols such as ethanol.

[0085] According to a particular embodiment of the present invention, the composition comprises a mixture of polar protic organic solvents different from each other, in particular a mixture of one or two (C2-C6)alkanediols, preferably two (C2-C4)alkanediols and a (C2-C6)alkanol, preferably a (C2-C4)alkanol such as ethanol.

[0086] According to another particular embodiment of the present invention, the composition comprises a mixture of the following polar protic organic solvents that are different from each other: two or more (C2-C6)alkanediols, preferably two (C2-C4)alkanediols.

[0087] The substance that is liquid at room temperature and ambient pressure may be present in an amount greater than or equal to 1% by weight, in particular in an amount greater than or equal to 9% by weight, more particularly in an amount between 2% and 75% by weight, even more particularly between 3% and 50% by weight, preferably in an amount ranging from 3% to 20% by weight, more preferably in an amount ranging from 5% to 15% by weight, such as 9% by weight, relative to the total weight of the composition.

[0088] Preferably, the polar protic organic solvent may be present in an amount greater than or equal to 1% by weight, in particular in an amount greater than or equal to 9% by weight, more particularly in an amount between 2% and 75% by weight, even more particularly between 3% and 50% by weight, preferably in an amount ranging from 3% to 20% by weight, more preferably in an amount ranging from 5% to 15% by weight, such as 9% by weight, relative to the total weight of the composition.

[0089] According to one embodiment of the invention, the composition further comprises ii) at least one polar protic organic solvent, such as at least one polyol as defined above, in an amount less than or equal to 70% by weight, in particular less than or equal to 50% by weight, preferably less than or equal to 20% by weight, preferably between 1% and 15% by weight, more preferably between 5% and 12% by weight, such as 9% by weight, relative to the total weight of the composition.

[0090] Advantageously, the composition comprises i) at least one compound of formula (I) or (I') in an amount greater than 10% by weight relative to the total weight of the composition; and ii) at least one polar protic organic solvent, preferably at least one (C2-C6)alkane (poly)ol.

[0091] Advantageously, the composition comprises at least one compound of formula (I) or (I') in an amount greater than 10% by weight relative to the total weight of the composition; and at least one (C2-C6)alkane polyol, preferably at least one (C2-C6)alkane diol.

[0092] Advantageously, the composition comprises one or more compounds of formula (I), preferably (I'), in a content greater than 10% by weight; and at least one polar protic organic solvent chosen from the group consisting of propane-1,2-diol, propane-1,3-diol and mixtures thereof, more preferably 1,3-propylene glycol.

[0093] Preferably:

[0094] - the compound of formula (I) or (I') is present in a content ranging from 30% to 99% by weight, more preferably in a content ranging from 50% to 98% by weight, even more preferably in a content ranging from 6% to 97% by weight, better still in a content ranging from 70% to 96% by weight, even better still in a content ranging from 75% to 95% by weight, in particular in a content ranging from 80% to 94% by weight, more particularly in a content ranging from 85% to 93% by weight, such as 90% by weight, relative to the total weight of the composition, and

[0095] - the polar protic organic solvent is present in an amount greater than or equal to 1% by weight, in particular in an amount greater than or equal to 9% by weight, more particularly in an amount between 2% and 75% by weight, even more particularly between 3% and 50% by weight, preferably in an amount ranging from 3% to 20% by weight, more preferably in an amount ranging from 5% to 15% by weight, such as 9% by weight, relative to the total weight of the composition.

[0096] Preferably:

[0097] - the compound of formula (I) or (I') is present in a content ranging from 30% to 99% by weight, more preferably in a content ranging from 50% to 98% by weight, even more preferably in a content ranging from 60% to 97% by weight, better still in a content ranging from 70% to 96% by weight, even better still in a content ranging from 75% to 95% by weight, in particular in a content ranging from 80% to 94% by weight, more particularly in a content ranging from 85% to 93% by weight, such as 90% by weight, relative to the total weight of the composition, and

[0098] - Preferably, the polar protic organic solvent is present in an amount less than or equal to 70% by weight, in particular in an amount less than or equal to 50% by weight, preferably in an amount less than or equal to 20% by weight, preferably in an amount between 1% and 15% by weight, more preferably between 5% and 12%, such as 9% by weight, relative to the total weight of the composition.

[0099] According to one embodiment, the composition of the invention does not comprise liquid substances other than ii).

[0100] According to one embodiment, iii) another liquid substance different from the polar protic organic solvent is present in the composition of the invention, preferably water.

[0101] Preferably, iii) water is present in the composition according to the invention.

[0102] Preferably, the composition according to the invention comprises i) at least one compound of formula (I) or (I') in an amount greater than 10% by weight relative to the total weight of the composition; ii) at least one compound as previously defined which is active at room temperature (25°C) and atmospheric pressure (1.013×10 5 Pa) substances that are liquid below 300 Pa; and iii) water.

[0103] Advantageously, the composition according to the invention comprises i) at least one compound of formula (I) or (I') in an amount greater than 10% by weight relative to the total weight of the composition; and ii) at least one polar protic organic solvent; and iii) water.

[0104] Preferably, water may be present in a content less than or equal to 20% by weight, preferably less than or equal to 10% by weight, more preferably in a content ranging from 0.05% to 5% by weight, even more preferably in a content ranging from 0.5% to 3% by weight, better still in a content ranging from 0.8% to 1.5% by weight, such as 1% by weight, relative to the total weight of the composition.

[0105] Advantageously, the composition according to the invention comprises at least one compound of formula (I) or (I') in an amount greater than 10% by weight relative to the total weight of the composition; at least one polar protic organic solvent in an amount greater than or equal to 1% by weight relative to the total weight of the composition; and water in a content less than or equal to 20% by weight relative to the total weight of the composition.

[0106] Advantageously, the composition according to the invention comprises:

[0107] - at least one compound of formula (I) wherein R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2 represents a hydrogen atom; R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, in particular a C1 alkyl group, or a compound of formula (I') in an amount greater than 10% by weight relative to the total weight of the composition,

[0108] - at least one polar protic organic solvent in an amount greater than or equal to 1% by weight relative to the total weight of the composition, and

[0109] - Water, in a content less than or equal to 20% by weight relative to the total weight of the composition.

[0110] Advantageously,

[0111] - the compound of formula (I) or (I') is present in a content ranging from 75% to 95% by weight relative to the total weight of the composition,

[0112] - the substance that is liquid at room temperature and atmospheric pressure is a polar protic organic solvent, which is present in an amount ranging from 5% to 20% by weight relative to the total weight of the composition,

[0113] - Water may be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition.

[0114] Advantageously,

[0115] - a compound of formula (I), wherein R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2represents a hydrogen atom; R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, in particular a C1 alkyl group, or a compound of formula (I') is present in a content ranging from 75% to 95% by weight relative to the total weight of the composition,

[0116] - the substance that is liquid at room temperature and atmospheric pressure is a polar protic organic solvent, which is present in an amount ranging from 5% to 20% by weight relative to the total weight of the composition,

[0117] - Water may be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition.

[0118] Advantageously,

[0119] - the compound of formula (I) or (I') is present in a content ranging from 75% to 95% by weight relative to the total weight of the composition,

[0120] - the polar protic organic solvent is present in an amount ranging from 5% to 20% by weight relative to the total weight of the composition,

[0121] - Water may be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition.

[0122] Advantageously,

[0123] - a compound of formula (I), wherein R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2 represents a hydrogen atom; R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, in particular a C1 alkyl group, or a compound of formula (I'), preferably a compound of formula (I') present in a content ranging from 75% to 95% by weight relative to the total weight of the composition,

[0124] - the polar protic organic solvent is present in an amount ranging from 5% to 20% by weight relative to the total weight of the composition,

[0125] - Water may be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition.

[0126] More advantageously, the composition consists of:

[0127] i) 75% to 95% by weight of a compound of formula (I) or (I′) relative to the total weight of the composition,

[0128] ii) 5% to 20% by weight, relative to the total weight of the composition, of a substance that is liquid at room temperature and atmospheric pressure, chosen from the group consisting of polar protic organic solvents, and

[0129] iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

[0130] In other words, the composition advantageously consists of:

[0131] i) 75% to 95% by weight of a compound of formula (I) or (I′) relative to the total weight of the composition,

[0132] ii) 5% to 20% by weight of a polar protic organic solvent relative to the total weight of the composition, and

[0133] iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

[0134] Even better, the composition of the present invention consists of:

[0135] i) 75% to 95% by weight of a compound of formula (I) or (I′) relative to the total weight of the composition,

[0136] ii) 5% to 20% by weight, relative to the total weight of the composition, of a polar protic organic solvent, being a substance that is liquid at room temperature and atmospheric pressure, preferably a (C2-C6)alkanediol, more preferably chosen from propane-1,2-diol, propane-1,3-diol and mixtures thereof, even more preferably 1,3-propylene glycol, and

[0137] iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

[0138] In other words, the composition of the present invention consists of:

[0139] i) 75% to 95% by weight of a compound of formula (I) or (I′) relative to the total weight of the composition,

[0140] ii) 5% to 20% by weight relative to the total weight of the composition of a polar protic organic solvent, preferably a (C2-C6)alkanediol, more preferably chosen from propane-1,2-diol, propane-1,3-diol and mixtures thereof, even more preferably 1,3-propylene glycol, and

[0141] iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

[0142] Even better, the composition of the present invention consists of:

[0143] i) 75% to 95% by weight, relative to the total weight of the composition, of a compound of formula (I), wherein R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2 represents a hydrogen atom; R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, especially a C1 alkyl group, or a compound of formula (I'), preferably a compound of formula (I'),

[0144] ii) 5% to 20% by weight relative to the total weight of the composition of a polar protic organic solvent, preferably a (C2-C6)alkanediol, more preferably chosen from propane-1,2-diol, propane-1,3-diol and mixtures thereof, even more preferably 1,3-propylene glycol, and

[0145] iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

[0146] According to a preferred embodiment of the present invention, the composition consists of: i) 90% ± 5% by weight of a compound of formula (I) or (I'); ii) 9% ± 2% by weight of a polar protic organic solvent, in particular a polyol, preferably a (C2-C6) alkane diol, more preferably selected from the group consisting of propane-1,2-diol, propane-1,3-diol, butanediol and mixtures thereof, even more preferably 1,3-propylene glycol; and 1% ± 0.5% by weight of water, with the proviso that the sum of components i) + ii) + iii) is equal to 100%.

[0147] According to a preferred embodiment of the present invention, the composition consists of: i) 90% ± 5% by weight of a compound of formula (I) or (I'); ii) 9% ± 2% by weight of a polar protic organic solvent, in particular a polyol, preferably a (C2-C6) alkane diol, more preferably selected from the group consisting of propane-1,2-diol, propane-1,3-diol, butanediol and mixtures thereof, even more preferably 1,3-propylene glycol; and 1% ± 0.5% by weight of water, with the proviso that the sum of components i) + ii) + iii) is equal to 100%.

[0148] According to a more preferred embodiment of the present invention, the composition consists of: i) 90% by weight of a compound of formula (I'); ii) 9% by weight of 1,3-propylene glycol, as a substance that is liquid at room temperature and atmospheric pressure; and 1% by weight of water, relative to the total weight of the composition.

[0149] According to a more preferred embodiment of the present invention, the composition consists of: i) 90% by weight of the compound of formula (I'), ii) 9% by weight of 1,3-propylene glycol, and 1% by weight of water, relative to the total weight of the composition.

[0150] The composition according to the invention can be used for the preparation of a cosmetic, dermatological, pharmaceutical or nutraceutical composition, preferably a cosmetic composition.

[0151] The compositions according to the invention are particularly compatible with keratin materials such as the skin of the face or body, the lips, the hair, the eyelashes, the eyebrows and the nails.

[0152] The composition according to the invention may also contain adjuvants customary in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, active cosmetic agents, fragrances, fillers, colorants, moisturizers, vitamins and polymers. The amounts of these various adjuvants are those conventionally used in the field under consideration, for example, from 0.001% to 20% by weight of the total composition. These adjuvants and their concentrations must be such that they do not impair the advantageous properties of the compound according to the invention.

[0153] use

[0154] A subject of the present invention is likewise the use of a composition according to the invention as defined above for improving the microbial preservation of cosmetic, dermatological, pharmaceutical or nutraceutical compositions, preferably cosmetic compositions.

[0155] A subject of the present invention is also the use of a composition as defined above for improving the stability of a compound of formula (I) or (I'), in particular at temperatures ranging from 15°C to 40°C, and in particular from 20°C to 40°C, and / or the use of a composition according to the invention as defined above for slowing down the recrystallization of a compound of formula (I) or (I') at temperatures ranging from 15°C to 40°C, and in particular from 20°C to 40°C.

[0156] Advantageously, the invention relates to the use of a composition as defined above, comprising:

[0157] - a compound of formula (I) or (I') in an amount ranging from 75% to 95% by weight relative to the total weight of the composition,

[0158] - a polar protic organic solvent in an amount ranging from 5 to 20% by weight relative to the total weight of the composition,

[0159] - water can be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition,

[0160] The use serves to slow down the recrystallization of the compound of formula (I) or (I'), in particular at a temperature ranging from 15 to 40°C, and in particular from 20 to 40°C.

[0161] More advantageously, the invention relates to the use of a composition as defined above, consisting of:

[0162] i) 75% to 95% by weight of a compound of formula (I) or (I′) relative to the total weight of the composition,

[0163] ii) 5% to 20% by weight, relative to the total weight of the composition, of a substance that is liquid at room temperature and atmospheric pressure, chosen from the group consisting of polar protic organic solvents, and

[0164] iii) 0.05% to 5% by weight of water relative to the total weight of the composition;

[0165] The use serves to slow down the recrystallization of the compound of formula (I) or (I'), in particular at a temperature ranging from 15 to 40°C, and in particular from 20 to 40°C.

[0166] Even better, the invention relates to the use of a composition as defined above, consisting of:

[0167] i) 75% to 95% by weight of a compound of formula (I) or (I′) relative to the total weight of the composition,

[0168] ii) 5% to 20% by weight, relative to the total weight of the composition, of a polar protic organic solvent, being a substance that is liquid at room temperature and atmospheric pressure, preferably a (C2-C6)alkanediol, more preferably chosen from propane-1,2-diol, propane-1,3-diol and mixtures thereof, even more preferably 1,3-propylene glycol, and

[0169] iii) 0.05% to 5% by weight of water relative to the total weight of the composition;

[0170] The use serves to slow down the recrystallization of the compound of formula (I) or (I'), in particular at a temperature ranging from 15 to 40°C, and in particular from 20 to 40°C.

[0171] Even better, the invention relates to the use of a composition as defined above, consisting of:

[0172] i) 75% to 95% by weight, relative to the total weight of the composition, of a compound of formula (I), wherein R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as an ethyl group; R 2 represents a hydrogen atom; R 3represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, especially a C1 alkyl group, or a compound of formula (I'), preferably a compound of formula (I'),

[0173] ii) 5% to 20% by weight, relative to the total weight of the composition, of a polar protic organic solvent, being a substance that is liquid at room temperature and atmospheric pressure, preferably a (C2-C6)alkanediol, more preferably chosen from propane-1,2-diol, propane-1,3-diol and mixtures thereof, even more preferably 1,3-propylene glycol, and

[0174] iii) 0.05% to 5% by weight of water relative to the total weight of the composition;

[0175] The use serves to slow down the recrystallization of the compound of formula (I) or (I'), in particular at a temperature ranging from 15 to 40°C, and in particular from 20 to 40°C.

[0176] method

[0177] Another subject of the present invention is a process for manufacturing a commercial or industrial product using one or more compounds of formula (I) or (I'), comprising the step of adding a composition according to the invention to said manufacturing process.

[0178] Preferably, the process is a process for manufacturing a commercial or industrial product using one or more compounds of formula (I'), comprising the step of adding the composition of the invention to said manufacturing process. DETAILED DESCRIPTION

[0179] The present invention is described in more detail in the following non-limiting examples.

[0180] Examples:

[0181] The following composition was prepared:

[0182] [Table 1]

[0183]

[0184] Compound i) 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one crystallized in less than 6 h at 15°C and in less than 16 h, within 1 day at 25°C.

[0185] It is observed that the composition of the invention makes it possible to significantly slow down the recrystallization of the compound of formula (I) or (I′) and to obtain a stability of the composition over time, even after weeks or even months.

[0186] For example, for composition 5, compound i) starts to crystallize after 17 h at a temperature of 15° C., and this same compound i) remains liquid after 72 h at a temperature of 25° C. Finally, it appears that composition 5 remains stable over time even after several weeks or even months at room temperature (25° C.).

Claims

1. A composition comprising i) one or more 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one derivatives of the following formula (I): In formula (I): -R 1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 6 carbon atoms; -R 2 represents a hydrogen atom or a C2-C4 alkyl group such as a methyl or ethyl group; -R 3 represents a linear or branched, saturated or unsaturated hydrocarbon group containing 1 to 12 atoms, which is optionally substituted by an aryl group; the aryl group is preferably a phenyl group which is optionally substituted by one or more groups selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy and combinations thereof; and also one of its optical isomers or geometric isomers, and / or one of its salts with an organic or inorganic acid or base, and / or one of its solvates, such as a hydrate; It is understood that the compound of formula (I) is present in a content greater than 10% by weight relative to the total weight of the composition, -ii) one or more substances which are liquid at room temperature and atmospheric pressure and are chosen from polar protic organic solvents, -iii) optionally water.

2. The composition according to claim 1, characterized in that In formula (I), R 2 Represents a hydrogen atom.

3. The composition according to claim 1 or 2, characterized in that In formula (I), R 3 represents a C1-C6 alkyl group; preferably a C1-C4, more preferably a C1-C3, and especially a C1 alkyl group.

4. The composition according to any one of the preceding claims, characterized in that In formula (I), R 1 represents a C1-C4 alkyl group, more preferably a C2-C4 alkyl group such as ethyl group.

5. The composition according to any one of the preceding claims, characterized in that The compound of formula (I) corresponds to the following formula (I'):

6. The composition according to any one of the preceding claims, characterized in that The compound of formula (I) is present in a content greater than or equal to 20% by weight, preferably at a content greater than or equal to 30% by weight, more preferably at a content greater than or equal to 40% by weight, even more preferably at a content greater than or equal to 50% by weight, even better still at a content greater than or equal to 60% by weight, in particular at a content greater than or equal to 70% by weight, more particularly at a content greater than or equal to 80% by weight and especially at a content greater than or equal to 90% by weight relative to the total weight of the composition.

7. The composition according to any one of the preceding claims, characterized in that The compound of formula (I) is present in a content ranging from 30% to 99% by weight, preferably in a content ranging from 50% to 98% by weight, more preferably in a content ranging from 60% to 97% by weight, even more preferably in a content ranging from 70% to 96% by weight, better still in a content ranging from 75% to 95% by weight, even better still in a content ranging from 80% to 94% by weight, in particular in a content ranging from 85% to 93% by weight, such as 90% by weight, relative to the total weight of the composition.

8. The composition according to any one of the preceding claims, characterized in that The polar protic organic solvent is selected from (C2-C 10 )alkane (poly)ols, preferably the group consisting of (C2-C6)alkane (poly)ols.

9. The composition according to any one of the preceding claims, characterized in that The polar protic organic solvent is propylene glycol.

10. The composition according to any one of the preceding claims, characterized in that The liquid substance is present in an amount greater than or equal to 1% by weight, in particular in an amount greater than or equal to 9% by weight, more particularly in an amount between 2% and 75% by weight, even more particularly between 3% and 50% by weight, preferably in an amount ranging from 3% to 20% by weight, more preferably in an amount ranging from 5% to 15% by weight, such as 9% by weight, relative to the total weight of the composition.

11. The composition according to any one of the preceding claims, characterized in that The water may be present in a content less than or equal to 20% by weight, preferably less than or equal to 10% by weight, more preferably in a content ranging from 0.05% to 5% by weight, even more preferably in a content ranging from 0.5% to 3% by weight, better still in a content ranging from 0.8% to 1.5% by weight, such as 1% by weight, relative to the total weight of the composition.

12. The composition according to any one of the preceding claims, characterized in that: - said compound of formula (I) or (I') is present in a content ranging from 75% to 95% by weight relative to the total weight of said composition, - said substance that is liquid at room temperature and atmospheric pressure is a polar protic organic solvent, present in an amount ranging from 5% to 20% by weight relative to the total weight of said composition, - Water may be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition.

13. A composition according to any one of the preceding claims, consisting of: i) 75% to 95% by weight of a compound of formula (I) or (I') relative to the total weight of the composition, ii) 5% to 20% by weight, relative to the total weight of the composition, of a substance that is liquid at room temperature and atmospheric pressure, said substance being chosen from the group consisting of polar protic organic solvents, and iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

14. The composition according to any one of the preceding claims, characterized in that The composition comprises: i) 75% to 95% by weight of a compound of formula (I) or (I') relative to the total weight of the composition, ii) 5% to 20% by weight, relative to the total weight of the composition, of a substance that is liquid at room temperature and atmospheric pressure, said substance being chosen from polar protic organic solvents, preferably (C2-C6)alkane diols, more preferably from propane-1,2-diol, propane-1,3-diol and mixtures thereof, even more preferably 1,3-propylene glycol, and iii) 0.05% to 5% by weight of water relative to the total weight of the composition.

15. A composition according to any one of the preceding claims, consisting of: i) 90% ± 5% by weight of a compound of formula (I) or (I'); ii) 9% ± 2% by weight of a polar protic organic solvent, in particular a polyol, preferably a (C2-C6)alkanediol, more preferably selected from the group consisting of propane-1,2-diol, propane-1,3-diol, butanediol and mixtures thereof, even more preferably 1,3-propylene glycol, as a substance that is liquid at room temperature and atmospheric pressure; and 1% ± 0.5% by weight of water, with the proviso that the sum of components i) + ii) + iii) is equal to 100%.

16. A composition according to any one of the preceding claims, consisting of: Relative to the total weight of the composition, i) 90% by weight of a compound of formula (I'); ii) 9% by weight of 1,3-propylene glycol as a liquid substance at room temperature and atmospheric pressure; and 1% by weight of water.

17. Use of a composition according to any one of the preceding claims for improving the microbial preservation of a cosmetic composition.

18. Use of the composition according to any one of claims 1 to 16 for improving stability, in particular at temperatures ranging from 15°C to 40°C, and in particular from 20°C to 40°C, preferably for slowing down the recrystallization of the compound of formula (I) or (I′) at temperatures ranging from 15°C to 40°C, and in particular from 20°C to 40°C.

19. A process for the manufacture of a commercial or industrial product, preferably a cosmetic product, using one or more compounds of formula (I) or (I'), said process comprising the step of adding a composition according to any one of claims 1 to 16 to said manufacturing process.

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