EP4642422A1

EP4642422A1 - Composition comprising more than ten percent by weight of 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one derivatives

Info

Publication number: EP4642422A1
Application number: EP23841231.6A
Authority: EP
Inventors: Nicolas FLEURYBREGEOT; Patricio Guerreiro
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2022-12-28
Filing date: 2023-12-28
Publication date: 2025-11-05
Also published as: FR3144522A1; WO2024141594A1; CN120529892A

Abstract

The present invention relates to a composition comprising more than ten percent by weight of 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one derivative corresponding to formula (I), as described below, at least one substance that is liquid at room temperature and ambient pressure chosen from polar protic organic solvent(s), and optionally water. The invention also relates to the use of a composition according to the invention for improving the microbial preservation of cosmetic compositions.

Description

DESCRIPTION

TITLE: Composition comprising more than ten percent by weight of 4- (3-ethoxy-4-hydroxyphenyl)butan-2-one derivatives

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

The invention also relates to the use of a composition according to the invention for improving the microbial preservation of cosmetic compositions.

Microorganisms can survive and spread relatively easily in cosmetic, dermatological, pharmaceutical, and food products that do not contain preserving agents.

Preserving agents are thus regularly added to most industrial preparations intended to be stored or preserved in order to prevent microbial growth over time. Microbial contamination during the production of an industrial product is common, even when the starting ingredients placed in said product are “clean”, i.e. free of contaminating microorganisms.

Water, for example, which is omnipresent in most cosmetic, pharmaceutical, dermatological or even nutraceutical products, must be free of contaminating microorganisms. Similarly, the other ingredients must also be screened for the presence of contaminating microorganisms. The cleanliness during the production of these industrial products, the processing of the contents and the filling of the containers must be scrupulously monitored in order to minimize, or even eliminate, the presence of contaminating microorganisms.

Despite these precautions, the microbial integrity of products of this type may require the presence of one or more preserving agents or preservatives that are compatible with the product and the stability of the composition. The products must allow neither growth nor viability of contaminating microorganisms.

In addition, maintaining cleanliness during the use of such products still remains problematic, notably when they are grasped, because fingers, applicators, for example cosmetic applicators, and even the ambient air are not sterile. Preserving agents thus prove necessary in order to reduce contamination with microorganisms by consumers during normal use. As a general rule, pathogenic microorganisms must be absent from all products sold, notably cosmetic products Kirk Othmer Encyclopedia, Cosmetics, Martin M. Rieger, 04/12/2000). Over the years, preserving problems have also led to the introduction of preserving agents with a varied spectrum of action in order to combat resistant contaminating microorganisms.

The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and derivatives thereof are preserving agents commonly used in compositions, notably cosmetic compositions, for the advantageous performance thereof against various strains of bacteria, both Gram-positive bacteria and Gram- negative bacteria, 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.

The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and derivatives thereof are generally used, alone or as a mixture, with other preserving or nonpreserving compounds, to effectively protect various compositions, notably cosmetic compositions, from microbial contamination both during preparation and during the use thereof in daily life.

The compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one, also known as ethylzingerone, may for example be prepared from ethylvanillin according to the following synthetic pathway (A): in which synthetic pathway (A): either R2 represents a hydrogen atom and R3 represents a linear (saturated) C1-C6 alkyl radical, optionally substituted with a hydroxyl group; or else a linear C2-C6 alkenyl (C=C unsaturated) radical, or alternatively a linear C2-C12 alkenyl radical substituted with a hydroxyl group; or R2 represents a methyl or ethyl radical, and R3 represents a linear (saturated) C1-C6 alkyl radical, optionally substituted with a hydroxyl group; or else a linear C2-C6 alkenyl (C=C unsaturated) radical, or alternatively a linear C2-C12 alkenyl radical substituted with a hydroxyl group.

However, once synthesized, ethylzingerone and the derivatives thereof generally have the drawback of not being sufficiently stable in various compositions because the latter may crystallize at temperatures likely to vary from 15 °C to 40°C.

Thus, despite the advantageous antimicrobial properties thereof, the use thereof may prove to be limited both after the preparation thereof and during the formulation thereof in cosmetic, pharmaceutical, dermatological or nutraceutical compositions, in particular cosmetic compositions, or over a relatively long period corresponding to the transportation and/or storage thereof prior to being used as an antimicrobial agent in such compositions.

As a result, these risks of crystallization may also hinder the antimicrobial efficacy of these derivatives, particularly in cosmetic applications.

Furthermore, during the industrial-scale manufacture of compositions, in particular cosmetic compositions, comprising the compound 4-(3-ethoxy-4- hydroxyphenyl)butan-2-one and derivatives thereof of formula (I) or (I'), as described below, it was found that during the manufacturing and formulating process, said compounds of formula (I) and in particular (I’) are difficult to handle because they tend to recrystallize in the pipes and other inlet means of an industrial reactor. In addition to the problems of clogging, subsequent cleaning, and losses of amounts of compounds of formula (I) and in particular (I’), the amount that is ultimately actually present in the composition, in particular cosmetic composition, is modified, which in terms of quality becomes difficult to manage during large-scale production, and poses difficulties in terms of reproducibility.

In other words, the recrystallization of the compounds of formula (I), in particular of formula (I’), at the stage of the manufacture, transportation, storage, handling and/or formulation thereof, has a great impact on the final amounts of compound actually present in the compositions, in particular cosmetic compositions.

It is therefore of great interest to be able to manufacture commercial products which comprise at least ethylzingerone and derivatives thereof of formula (I) or (I’), which can be handled, and for which it is possible to anticipate with greater certainty - when it is necessary to add the compounds of formula (I) or (I’) in a large amount to a composition comprising other, notably cosmetic ingredients and active agents and in particular on an industrial scale - the amount which will ultimately be present in said products.

There is therefore a real need to provide a composition comprising the compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and/or one of the derivatives thereof, which does not exhibit the abovementioned drawbacks, that is to say compositions in which such compounds are stable, in particular at temperatures which may range from 15 °C to 40°C and in particular from 20°C to 40°C.

In other words, one of the objectives of the present invention is to provide a composition which is stable, in particular at temperatures which can range from 15°C to 40°C and in particular from 20°C to 40°C, in which the risks of crystallization of the compound 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and of the derivatives thereof are minimized, or are significantly slowed down.

This technical problem has been solved by using, in the process for the preparation of cosmetic or pharmaceutical products, a composition 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 greater than 10% by weight, and one or more substances that are liquid at room temperature (25°C) and atmospheric pressure (1.013xl0⁵ Pa). Preferably, the liquid substance(s) is (are) chosen from (non)polar (a)protic solvents, more preferably from polar protic solvents. Preferably, the liquid substance(s) is (are) chosen from (non)polar (a)protic organic solvents, more preferentially from polar protic organic solvents.

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 the optical isomers or geometrical isomers thereof, and/or one of the salts thereof with an organic or inorganic acid or base, and/or one of the solvates thereof such as the hydrates, ii) one or more substances that are liquid at room temperature and atmospheric pressure, iii) optionally water.

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

More particularly, one subject of the present invention is notably a composition comprising i) one or more compounds of formula (I) below: in which formula (I):

- R¹ represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 6 carbon atoms;

- R² represents a hydrogen atom or a C2-C4 alkyl group, such as methyl or ethyl;

- R³ represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 12 atoms, optionally substituted with an aryl group; the aryl group preferably being a phenyl group optionally substituted with one or more groups chosen from hydroxyl, C1-C4 alkyl group, C1-C4 alkoxy group and combinations thereof; and also one of the optical isomers or geometrical isomers thereof, and/or one of the salts thereof with an organic or inorganic acid or base, and/or one of the solvates thereof, such as the hydrates;

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

- iii) optionally water; it being understood that i) said compound(s) of formula (I) are present in a content of greater than 10% by weight, relative to the total weight of the composition.

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

In other words, the composition according to the invention makes it possible to stabilize at least one compound of formula (I), both on conclusion of the preparation thereof, by reducing in particular the risks of recrystallization, and during the transportation and/or storage thereof, and the use thereof in the production of commercial products in order to be used as an antimicrobial agent in various applications, including cosmetic applications.

The composition according to the invention can thus advantageously be stored, used in production plants and/or transported for a relatively long period at temperatures which can range from 15°C to 40°C and in particular from 20°C to 40°C, while reducing the risks of crystallization of the compound of formula (I).

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

In other words, the composition according to the invention makes it possible to minimize, or significantly slow down, the risks of crystallization of a compound of formula (I) or (I’), thus guaranteeing an effective use thereof as an antimicrobial agent in various applications, in particular in cosmetic applications.

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

A subject of the invention is thus also the use of a composition according to the invention for improving the stability of the compound(s) 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 the compound(s) of formula (I) or (T) at a temperature ranging from 15°C to 40°C, and in particular ranging from 20°C to 40°C.

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

Another subject of the invention is a process for manufacturing commercial or industrial products using one or more compounds of formula (I) or (I’), comprising the step of adding, to said manufacturing process, the composition of the invention.

It appears that the recrystallization step is slowed down by a few minutes to several days at the same temperature and atmospheric pressure, in the manufacturing process, and in particular in the step of adding to the process, and prevents the formation of impurities of the product and various liquid substances, in particular solvents. Other subjects, characteristics, aspects and advantages of the invention will become still more clearly apparent on reading the description and the example which follow.

In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions “ of between” and “ranging from ... to ... ”.

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .

In addition, the expression "at least" used in the present description is equivalent to the expression "greater than or equal to". Finally, in a way known per se, the term "C_n" or "Cn" compound or group denotes a compound or a group containing, in its chemical structure, "n" carbon atoms.

Within the meaning of the present invention, the terms “alkaline agent” and “basifying agent” are used without distinction.

The basifying agent(s) can be inorganic alkaline agents, preferably chosen from the group constituted of alkali metal hydroxides or alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, alkali metal or alkaline earth metal (bi)carbonates, such as sodium or potassium (bi)carbonates, and mixtures thereof. The basifying agent(s) can be organic alkaline agents, preferably chosen from the group consisting of mono(Ci- C6)(hydroxy)alkylamines, di(Ci-C6)(hydroxy)alkylamines, tri(Ci-

C6)(hydroxy)alkylamines (preferably tri(Ci-C6)(hydroxy)alkylamines), saturated or unsaturated cyclic amines which are aromatic, such as pyridine, or non-aromatic, optionally substituted by one or more (Ci-C4)alkyl groups, such as tetrahydropyridine optionally substituted by one or more (Ci-C4)alkyl groups, piperidine optionally substituted by one or more (C i -C4)alkyl groups or piperazine optionally substituted by one or more (Ci-C4)alkyl groups. Preferably, the alkaline agents of the invention are tertiary amines.

Preferably, the basifying agents are chosen from the group constituted of alkali metal or alkaline earth metal hydroxides, in particular sodium hydroxide, alkali metal or alkaline earth metal (bi)carbonates, in particular sodium or potassium (bi)carbonates, and tri(Ci-C6)(hydroxy)alkylamines, in particular tri(Ci- Cejalkylamines, notably triethylamine.

More preferentially, the basifying agents are inorganic and are chosen from the group constituted of alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal (bi)carbonates, and mixtures thereof, in particular alkali metal or alkaline earth metal hydroxides, in particular sodium hydroxide.

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

Preferably, in formula (I), R¹ represents a linear, saturated or unsaturated hydrocarbon group comprising from 1 to 6 carbon atoms.

Preferably, in formula (I), R¹ represents a linear, saturated hydrocarbon group comprising from 1 to 6 carbon atoms.

Preferably, in formula (I), R³ represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 12 carbon atoms.

Preferably, in formula (I), R² represents a hydrogen atom.

Preferably, in formula (I), R³ represents a Ci-Ce alkyl group; preferably a Ci- C4, more preferentially C1-C3, in particular Ci alkyl group.

Preferably, in formula (I), R³ represents a linear or branched, preferably linear, Ci-Cealkyl group; preferably a linear or branched, preferably linear, C1-C4 alkyl group, more preferentially linear or branched, preferably linear, C1-C3, in particular Ci alkyl group.

Preferably, in formula (I), R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl.

Advantageously, in formula (I), R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom.

Advantageously, in formula (I), R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R³ represents a Ci-Ce alkyl group; preferably, a C1-C4, more preferentially C1-C3, in particular Ci alkyl group.

Advantageously, in formula (I), R² represents a hydrogen atom and R³ represents a Ci-Ce alkyl group; preferably, a C1-C4, more preferentially C1-C3, in particular Ci alkyl group.

Advantageously, R¹ represents a C1-C4 alkyl group, more preferentially a C2- C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially C1-C3, in particular Ci alkyl group.

Advantageously, R¹ represents a linear C 1 -C4 alkyl group, more preferentially a linear C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a linear Ci-Ce alkyl group; preferably a linear C1-C4, more preferentially C1-C3, in particular Ci alkyl group.

Preferably, the compound of formula (I) is a compound corresponding to formula (I’) below:

(D

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

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

If the composition of the invention comprises several different compounds of formula (I), “an amount or a content of greater than 10% by weight” is understood to mean that the sum, by weight, of the compounds of formula (I) is strictly greater than 10% by weight, relative to the total weight of the composition, that is to say that the value of 10% by weight is excluded.

According to a particular embodiment of the invention, the composition comprises only one compound of formula (I), more preferentially of formula (I’).

Preferably, the compound(s) of formula (I) or (I’) is (are) present in a content of greater than or equal to 20% by weight, more preferentially in a content of greater than or equal to 30% by weight, even more preferentially in a content of greater than or equal to 40% by weight, better still in a content of greater than or equal to 50% by weight, even better still in a content of greater than or equal to 60% by weight, in particular in a content of greater than or equal to 70% by weight, more particularly in a content of greater than or equal to 80% by weight, notably in a content of greater than or equal to 90% by weight, relative to the total weight of the composition according to the invention. Preferably, the compound(s) of formula (I) or (I’) is (are) present in a content ranging from 30% to 99% by weight, more preferentially in a content ranging from 50% to 98% by weight, even more preferentially 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(s) of formula (I) or (I’) is (are) 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.

According to one embodiment of the invention, the composition comprises, as liquid substance(s) ii), at least one polar protic organic solvent.

Preferably, the polar protic organic solvent(s) ii) is (are) chosen from polyols.

Preferably, the liquid substance(s) are chosen from the group constituted of polar protic organic solvents, such as polyols.

The term "(poly)ol" is understood to mean a compound which is liquid at room temperature (25°C) and at atmospheric pressure (1.013xl0⁵ Pa) comprising a hydrocarbon chain of between C2 and C10, particularly between C2 and C5, more particularly between C3 and C4, such as C3, which is linear or branched, saturated or unsaturated, preferably saturated and comprising one or more hydroxyl groups, preferably comprising between 2 and 5 hydroxyl groups, more particularly comprising between 2 and 3, more preferentially 2 hydroxyl groups.

Preferably, the (poly)ol(s) is (are) chosen from (C2-Cio)alkane(poly)ols, more preferentially chosen from (C2-C6)alkane(poly)ols.

For the purposes of the present invention, the term "(C2-Cio)alkane(poly)ol" is understood to mean a linear or branched, preferably linear, alkane comprising from

1 to 10 carbon atoms and comprising one or more hydroxyl (-OH) groups, preferably

2 or 3 hydroxyl groups, more preferentially 2 hydroxyl groups.

In particular, the polar protic organic solvent(s) is (are) a (C2-C6)alkanediol or (C2-C6)alkanetriol, preferably (C2-C6)alkanediol. More preferentially, the (non)polar (a)protic organic solvent(s) is (are) a (C2-C4)alkanediol or (C2- C4)alkanetriol, preferably (C2-C4)alkanediol.

Preferably, the polar protic organic solvent is propanediol, in particular chosen from the group constituted of propane- 1,2-diol (or propylene glycol), propane- 1,3-diol, butane- 1,3-diol (or butylene glycol) and mixtures thereof, preferably 1,3- propanediol.

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

According to a particular embodiment of the invention, the composition comprises a mixture of polar protic organic solvents different from one another, in particular a mixture of one or two (C2-C6)alkanediols, preferably two (C2- C4)alkanediols with a (C2-C6)alkanol, preferably (C 2 -C 4) alkanol such as ethanol.

According to another particular embodiment of the invention, the composition comprises a mixture of polar protic organic solvents different from one another: two or more (C2-C6)alkanediols, preferably two (C2-C4)alkanediols.

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

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

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 of less than or equal to 70% by weight, particularly in an amount of less than or equal to 50%, preferably in an amount of less than or equal to 20% by weight, preferably in an amount of between 1% and 15%, more preferentially between 5% and 12% such as 9% by weight relative to the total weight of the composition.

Advantageously, the composition comprises i) at least one compound of formula (I) or (I’), in an amount of 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.

Advantageously, the composition comprises at least one compound of formula (I) or (I’), in an amount of greater than 10% by weight, relative to the total weight of the composition, and at least one (C2-C6)alkanepolyol, preferably at least one (C2-C6)alkanediol.

Advantageously, the composition comprises a content of more than 10% by weight of one or more compounds of formula (I), preferably (I’), and at least one polar protic organic solvent chosen from the group constituted of propane- 1,2-diol, propane- 1,3-diol and mixtures thereof, more preferentially 1,3-propanediol.

Preferably:

- the compound of formula (I) or (I’) is present in a content ranging from 30% to 99% by weight, more preferentially in a content ranging from 50% to 98% by weight, even more preferentially 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

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

Preferably:

- the compound of formula (I) or (I’) is present in a content ranging from 30% to 99% by weight, more preferentially in a content ranging from 50% to 98% by weight, even more preferentially 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 - the polar protic organic solvent is present in an amount of less than or equal to 70% by weight, particularly in an amount of less than or equal to 50%, preferably in an amount of less than or equal to 20% by weight, preferably in an amount of between 1% and 15%, more preferentially between 5% and 12% such as 9% by weight relative to the total weight of the composition.

According to one embodiment, the composition of the invention comprises no liquid substances other than ii).

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

Preferably, iii) water is present in the composition according to the invention. Preferably, the composition according to the invention comprises i) at least one compound of formula (I) or (I’), in an amount of greater than 10% by weight, relative to the total weight of the composition, ii) at least one substance that is liquid at room temperature (25°C) and atmospheric pressure (1.013xl0⁵ Pa) as previously defined, and iii) water.

Advantageously, the composition according to the invention comprises i) at least one compound of formula (I) or (I’), in an amount of 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.

Preferably, the water may be present in a content of less than or equal to 20% by weight, preferably less than or equal to 10% by weight, more preferentially in a content ranging from 0.05% to 5% by weight, even more preferentially 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.

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

Advantageously, the composition according to the invention comprises: at least one compound of formula (I), in which R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially a C1-C3, in particular a Ci alkyl group, or of formula (I’), in an amount of greater than 10% by weight, relative to the total weight of the composition, at least one polar protic organic solvent, in an amount of greater than or equal to 1% by weight, relative to the total weight of the composition, and water, in a content of less than or equal to 20% 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, relative to the total weight of the composition,

- the 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 the composition,

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

Advantageously,

- the compound of formula (I), in which R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially a C1-C3, in particular a Ci alkyl group, or of formula (I’), is present in a content ranging from 75% to 95% by weight, relative to the total weight of the composition,

- the water may be present in a content ranging from 0.05% to 5% 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% to 95% by weight, relative to the total weight of the composition,

- the polar protic organic solvent, is present in an amount ranging from 5% 20% by weight, relative to the total weight of the composition, - the water may be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition.

Advantageously,

- the compound of formula (I), in which R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially a C1-C3, in particular a Ci alkyl group, or of formula (I’), preferably of formula (I’), is present in a content ranging from 75% to 95% by weight, relative to the total weight of the composition,

- 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,

More advantageously, the composition consists of: i) 75% to 95% by weight of compound(s) of formula (I) or (I’), relative to the total weight of the composition, ii) 5% to 20% by weight of substance(s) that is (are) liquid at room temperature and atmospheric pressure chosen from the group constituted of polar protic organic solvent(s), relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition.

In other words, the composition advantageously consists of: i) 75% to 95% by weight of compound(s) of formula (I) or (I’), relative to the total weight of the composition, ii) 5% to 20% by weight of polar protic organic solvent(s), relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition.

Better still, the composition of the invention consists 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, as a substance that is liquid at room temperature and atmospheric pressure, of a polar protic organic solvent, preferably a (C2-C6)alkanediol, more preferentially chosen from propane- 1,2-diol, propane- 1,3 -diol and mixtures thereof, even more preferentially 1,3-propanediol, relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition.

In other words, the composition of the invention consists 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 of a polar protic organic solvent, preferably a (C2- C6)alkanediol, more preferentially chosen from propane- 1,2 -diol, propane- 1,3 -diol and mixtures thereof, even more preferentially 1,3-propanediol, relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition.

Better still, the composition of the invention consists of: i) 75% to 95% by weight of a compound of formula (I), in which R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially a C1-C3, in particular a Ci alkyl group, or of formula (I’), preferably of formula (I’), relative to the total weight of the composition, ii) 5% to 20% by weight of a polar protic organic solvent, preferably a (C2- C6)alkanediol, more preferentially chosen from propane- 1,2 -diol, propane- 1,3 -diol and mixtures thereof, even more preferentially 1,3-propanediol, relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition.

According to a preferred embodiment of the invention, the composition consists of i) 90% ± 5% by weight of compound of formula (I) or (I’), ii) 9% ± 2% by weight, as substance that is liquid at room temperature and atmospheric pressure, of polar protic organic solvent, notably of polyol, preferably a (C2-C6)alkanediol, more preferentially selected from the group constituted of propane- 1,2-diol, propane- 1,3- diol, butylene glycol and mixtures thereof, even more preferentially 1,3-propanediol, and 1% ± 0.5% by weight of water, provided that the sum of the ingredients i) + ii) + iii) is equal to 100%.

According to a preferred embodiment of the invention, the composition consists of i) 90% ± 5% by weight of compound of formula (I) or (I’), ii) 9% ± 2% by weight of polar protic organic solvent, notably of polyol, preferably a (C2- C6)alkanediol, more preferentially selected from the group constituted of propane- 1,2- diol, propane- 1,3-diol, butylene glycol and mixtures thereof, even more preferentially 1,3 -propanediol, and 1% ± 0.5% by weight of water, provided that the sum of the ingredients i) + ii) + iii) is equal to 100%.

According to a more preferred embodiment of the invention, the composition consists of i) 90% by weight of compound of formula (I’), ii) 9% by weight of 1,3- propanediol, as substance that is liquid at room temperature and atmospheric pressure, and 1% by weight of water relative to the total weight of the composition.

According to a more preferred embodiment of the invention, the composition consists of i) 90% by weight of compound of formula (I’), ii) 9% by weight of 1,3- propanediol, and 1% by weight of water relative to the total weight of the composition.

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

The composition according to the invention is in particular compatible with keratin materials such as the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and the nails.

The composition according to the invention may also comprise the adjuvants that are 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 fields under consideration, for example from 0.001% to 20% of the total weight of the composition. These adjuvants and the concentrations thereof must be such that they are not detrimental to the advantageous properties of the compounds according to the invention.

Use

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

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

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

- the compound of formula (I) or (I’) in a content ranging from 75% to 95% by weight, relative to the total weight of the composition,

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

- it being possible for water to be present in a content ranging from 0.05% to 5% by weight relative to the total weight of the composition, for slowing down the recrystallization of the compound(s) 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.

More advantageously, the invention relates to the use of a composition, as defined above, consisting of: i) 75% to 95% by weight of compound(s) of formula (I) or (I’), relative to the total weight of the composition, ii) 5% to 20% by weight of substance(s) that is (are) liquid at room temperature and atmospheric pressure chosen from the group constituted of polar protic organic solvent(s), relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition; for slowing down the recrystallization of the compound(s) 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.

Better still, the invention relates to the use of a composition, as defined above, 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, as a substance that is liquid at room temperature and atmospheric pressure, of a polar protic organic solvent, preferably a (C2-C6)alkanediol, more preferentially chosen from propane- 1,2-diol, propane- 1,3 -diol and mixtures thereof, even more preferentially 1,3-propanediol, relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition; for slowing down the recrystallization of the compound(s) 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.

Better still, the invention relates to the use of a composition, as defined above, consisting of: i) 75% to 95% by weight of a compound of formula (I), in which R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl; R² represents a hydrogen atom; R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially a C1-C3, in particular a Ci alkyl group, or of formula (I’), preferably of formula (I’), relative to the total weight of the composition, ii) 5% to 20% by weight, as a substance that is liquid at room temperature and atmospheric pressure, of a polar protic organic solvent, preferably a (C2-C6)alkanediol, more preferentially chosen from propane- 1,2-diol, propane- 1,3 -diol and mixtures thereof, even more preferentially 1,3-propanediol, relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition; for slowing down the recrystallization of the compound(s) 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.

Method

Preferentially, the process is a process for manufacturing commercial or industrial products using one or more compounds of formula (I’), comprising the step of adding, to said manufacturing process, the composition of the invention.

The invention is illustrated in more detail in the following non-limiting examples.

Examples: The following compositions were prepared:

[Table 1]

The compound i) 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one crystallizes at 15°C in less than 6 h and in less than 16 h at 25°C, in 1 day crystallized.

It was observed that the compositions of the invention make it possible to significantly slow down the recrystallization of the compounds of formula (I) or (I'), and to obtain a stability of the compositions over time even after several weeks or even months.

For example, for composition 5, compound i) begins 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. Composition comprising i) one or more 4-(3-ethoxy-4- hydroxyphenyl)butan-2-one derivatives of formula (I) below: in which formula (I):

- R³ represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 12 atoms, optionally substituted with an aryl group; the aryl group preferably being a phenyl group optionally substituted with one or more groups chosen from hydroxyl, C1-C4 alkyl group, C1-C4 alkoxy group and combinations thereof; and also one of the optical isomers or geometrical isomers thereof, and/or one of the salts thereof with an organic or inorganic acid or base, and/or one of the solvates thereof, such as the hydrates; it being understood that said compound(s) of formula (I) being present in a content of greater than 10% by weight, relative to the total weight of the composition,

- ii) one or more substances that are liquid at room temperature and atmospheric pressure and chosen from polar protic organic solvents,

- iii) optionally water.

2. Composition according to Claim 1, characterized in that, in formula (I), R² represents a hydrogen atom.

3. Composition according to Claim 1 or 2, characterized in that, in formula (I), R³ represents a Ci-Ce alkyl group; preferably a C1-C4, more preferentially C1-C3, in particular Ci alkyl group.

4. Composition according to any one of the preceding claims, characterized in that, in formula (I), R¹ represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl.

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

(D

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

7. 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 preferentially in a content ranging from 60% to 97% by weight, even more preferentially 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. Composition according to any one of the preceding claims, characterized in that the polar protic organic solvent is chosen from the group constituted of (C2- Cio)alkane(poly)ols, preferably (C2-C6)alkane(poly)ols.

9. Composition according to any one of the preceding claims, characterized in that the polar protic organic solvent is propanediol.

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

11. Composition according to any one of the preceding claims, characterized in that the water may be present in a content of less than or equal to 20% by weight, preferably less than or equal to 10% by weight, more preferentially in a content ranging from 0.05% to 5% by weight, even more preferentially 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. Composition according to any one of the preceding claims, characterized in that:

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

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

14. Composition according to any one of the preceding claims, characterized in that it consists 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 of a substance that is liquid at room temperature and atmospheric pressure chosen from polar protic organic solvents, preferably a (C2- C6)alkanediol, more preferentially chosen from propane- 1,2-diol, propane- 1,3- diol and mixtures thereof, even more preferentially 1,3-propanediol, relative to the total weight of the composition, and iii) 0.05% to 5% by weight of water, relative to the total weight of the composition.

15. Composition according to any one of the preceding claims, consisting of i) 90% ± 5% by weight of compound of formula (I) or (I’), ii) 9% ± 2% by weight, as substance that is liquid at room temperature and atmospheric pressure, of polar protic organic solvent, notably of polyol, preferably a (C2-C6)alkanediol, more preferentially selected from the group constituted of propane- 1,2-diol, propane- 1,3 -diol, butylene glycol and mixtures thereof, even more preferentially 1,3-propanediol, and 1% ± 0.5% by weight of water, provided that the sum of the ingredients i) + ii) + iii) is equal to 100%.

16. Composition according to any one of the preceding claims, consisting of i) 90% by weight of compound of formula (I’), ii) 9% by weight of 1,3-propanediol, as substance that is liquid at room temperature and atmospheric pressure, and 1% by weight of water relative to the total weight of the composition.

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

18. Use of a composition as defined in any one of Claims 1 to 16 for improving the 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(s) of formula (I) or (P) at a temperature ranging from 15°C to 40°C, and in particular ranging from 20°C to 40°C.

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