FR3135897A1 - HAIR COSMETIC COMPOSITIONS COMPRISING AT LEAST ONE NON-SILICONE LIPOPHILE CATIONIC POLYMER - Google Patents

Abstract

HAIR COSMETIC COMPOSITIONS COMPRISING AT LEAST ONE NON-SILICON LIPOPHILE CATIONIC POLYMER The present invention relates to a hair cosmetic composition, in particular for the treatment and/or care of keratin fibers, in particular hair, comprising at least one oily phase and at least one compound of formula (I) following: (I) in which: n is an integer from 1 to 5, X1 and X2, identical or different, represent -O-, -CH2- or -NH-, R1, R2 and R3, identical or different, independently represent a divalent alkylene radical comprising from 20 to 50 carbon atoms, R4 and R5, identical or different, represent, independently of each other, H, OH or NH2, at least one of the groups R4 and R5 representing NH2. Figure for the abstract: none

Description

HAIR COSMETIC COMPOSITIONS COMPRISING AT LEAST ONE NON-SILICONE LIPOPHILE CATIONIC POLYMER

The present invention relates to new hair cosmetic compositions comprising at least one cationic polymer. It also relates to the use of these compositions for the care and/or cosmetic treatment of keratin fibers, in particular hair.

Amodimethicone, also known as polydimethylsiloxane, is a synthetic silicon-based polymer (or “silicone polymer” or “amino functional silicone polymer”). Amodimethicone is a raw material used in particular in cosmetics, and in particular in hair care for hair care, and in particular to make it easier to comb, make it more docile, make it softer to the touch and make it more lustrous. In particular, amodimethicone helps coat the hair fiber, forming a thin film around the hair shaft and skin, which is desirable for better product adhesion and is also used for treated colored hair to protect and maintain color vibrancy.

The Applicant has also described the use of amodimethicone as a lipophilic polymer precursor of coacervate to stabilize emulsions, particularly macroscopic ones.

However, in cosmetics, we are seeing an increasingly strong demand from consumers for compositions devoid of silicone compounds due to their environmental impact, because they are non-biodegradable, and/or their suspected danger to health.

We are also seeing increasing consumer demand for cosmetic compositions including biosourced ingredients. This trend is illustrated in particular by the appearance of numerous labels such as "Cosmébio", "Natrue", "Cosmos" or "Ecocert", as well as the ISO 16128 standard relating to technical definitions and criteria applicable to cosmetic ingredients and products. natural and organic.

In particular, there is therefore a need for a non-silicone alternative to amodimethicone for the formulation of cosmetic compositions, particularly for hair.

The present invention therefore aims to provide hair cosmetic compositions comprising compounds, ideally biosourced or prepared from biosourced products, to replace silicone compounds, and in particular amodimethicone.

The present invention also aims to provide hair cosmetic compositions comprising a biosourced cationic polymer to replace amodimethicone.

Thus, the present invention relates to a hair cosmetic composition, in particular for the treatment and/or care of keratin fibers, in particular hair, comprising at least one oily phase and at least one compound of formula (I) below:

(I)

in which :

• n is an integer comprised from 1 to 5, preferably comprised from 1 to 3, preferably equal to 1 or 2,
• X ¹ and X ² , identical or different, represent ^, independently of each other, -O-, -CH ₂ - or -NH-, preferably at least ^one of the groups X ¹ and X ² , representing -NH-,
• R ¹ , R ² and R ³ , identical or different, independently represent a divalent, linear, cyclic or branched alkylene radical, comprising from 20 to 50 carbon atoms, preferably from 25 to 45 carbon atoms, better still from 30 to 40 carbon atoms, and preferably from 34 to 36 carbon atoms, R ¹ , R ² and R ³ being able to include a cycloalkylene radical comprising 3 to 10 carbon atoms, preferably comprising 6 carbon atoms, said radical cycloalkylene being optionally substituted by one or more alkyl chains comprising from 6 to 10 carbon atoms,
• R ⁴ and R ⁵ , identical or different, represent, independently of each other, H, OH or NH ₂ , at least one of the groups R ⁴ and R ⁵ representing NH ₂ .

As can be seen from the examples below, the inventors have shown that a cationic polymer according to the invention, also designated interchangeably in the rest of the description by the term "compound of formula (I)", allows the manufacture of cosmetic compositions. hair, endowed with satisfactory properties, or even equivalent to compositions comprising amodimethicone, particularly in terms of styling, detangling, shine and appearance and softness of the hair.

The examples below also show that the effects observed with a compound of formula (I) are obtained with much lower contents than those of amodimethicone.

As indicated above, the hair cosmetic composition according to the invention comprises at least one oily phase (or fatty phase).

Preferably, a fatty phase of a composition according to the invention has a melting point of between 50°C and 100°C, preferably between 60°C and 90°C.

The melting point of a fatty phase can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name "DSC Q2000" by the company TA Instruments. The sample preparation and measurement protocols are as follows: a 5 mg sample of the sample to be tested, previously heated to 80°C and taken with magnetic stirring using a spatula also heated, is placed in an airtight aluminum capsule, or crucible. Two tests are carried out to ensure the reproducibility of the results. The measurements are carried out on the calorimeter mentioned above. The oven is subjected to a nitrogen sweep. Cooling is ensured by the RCS 90 heat exchanger. The sample is then subjected to the following protocol by first being heated to 20°C, then subjected to a first rise in temperature ranging from 20°C to 130 °C, at a heating rate of 5°C/minute, then is cooled from 130°C to -80°C at a cooling rate of 5°C/minute and finally subjected to a second rise in temperature ranging from - 80°C to 130°C at a heating rate of 5°C/minute. During the second temperature rise, the variation in the difference in power absorbed by the empty crucible and by the crucible containing the sample is measured as a function of the temperature. The melting point of the compound is the temperature value corresponding to the top of the peak of the curve representing the variation of the difference in absorbed power as a function of temperature. The end of melting temperature corresponds to the temperature at which 95% of the sample has melted.

Unless otherwise indicated, in everything that follows, we consider that we are at ambient temperature (for example T = 25°C ± 2°C) and atmospheric pressure (760 mm of Hg, i.e. 1.013.10 ⁵ Pa or 1013 mbar ).

Compound of formula (I)

As indicated above, the hair cosmetic composition according to the invention comprises at least one compound corresponding to formula (I) as defined above.

The compound of formula (I) is a cationic polymer, and in particular a lipophilic cationic polymer. It is therefore present in the fatty phase of the cosmetic compositions according to the invention.

In the context of the present invention, an alkylene radical is a divalent radical corresponding to a linear or branched alkyl group with one less hydrogen atom, which can be represented by -C _x H _2x -, x representing the number of atoms of carbon.

In the context of the present invention, an alkyl group means a saturated, linear or branched hydrocarbon aliphatic group comprising from x to y carbon atoms. As examples, we can cite the groups n -eicosanyl (C ₂₀ H ₄₁ ), n -triacontane (C ₃₀ H ₆₁ ), n -tetracontane (C ₄₀ H ₈₁ ) or n -pentacontane (C ₅₀ H ₁₀₁ ) .

According to the present invention, a cycloalkylene radical is a divalent radical corresponding to a cycloalkyl group with one less hydrogen atom.

A cycloalkyl group is according to the present invention a cyclic carbon group comprising, unless otherwise stated, from 3 to 10 carbon atoms. As examples, mention may be made of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. groups.

Preferably, in formula (I) above, n is equal to 1 or 2.

In the following, the compounds according to the invention with n=1 may be designated "trimers", the compounds according to the invention with n=2 may be designated "pentamers", and the compounds according to the invention with n> 2 could indifferently be designated “higher degree oligomers”. Higher degree oligomers include heptamers in particular.

According to one embodiment, in the aforementioned formula (I), at least one of the groups R ⁴ and R ⁵ represents NH ₂ .

According to one embodiment, in formula (I), X ¹ and X ² are identical and represent, independently of each other, -O-, -CH ₂ - or -NH-, preferably -O- or -NH-.

According to one embodiment, in formula (I), at least one of the groups X ¹ and X ² represents -NH-.

According to a preferred embodiment, in formula (I), X ¹ and X ² represent -NH-.

According to a preferred embodiment, in formula (I), R ⁴ and R ⁵ represent NH ₂ .

According to a very particularly preferred embodiment, in formula (I), X ¹ and X ² represent -NH- and R ⁴ and R ⁵ represent NH ₂ .

According to one embodiment, in formula (I), R ¹ represents a linear or branched divalent alkylene radical, comprising from 20 to 50 carbon atoms, preferably from 25 to 45 carbon atoms, better still from 30 to 40 carbon atoms. carbon, and preferably from 34 to 36 carbon atoms. According to one embodiment, in formula (I), R ¹ represents a linear or branched divalent alkylene radical, comprising from 34 to 36 carbon atoms.

In a compound of formula where n > 1, the different R ¹ of said compound may be identical or different from each other.

According to one embodiment, in formula (I), R ² and R ³ , identical or different, preferably identical, represent independently of each other a divalent, linear or branched alkylene radical, comprising from 20 to 50 carbon atoms , preferably from 25 to 45 carbon atoms, better still from 30 to 40 carbon atoms, and preferably from 34 to 36 carbon atoms. According to one embodiment, in formula (I), R ² and R ³ , identical or different, preferably identical, represent independently of each other a divalent, linear or branched alkylene radical, comprising from 34 to 36 carbon atoms .

In a compound of formula where n > 1, the different R ² of said compound may be identical or different from each other.

The present invention also relates to a hair cosmetic composition as defined above, in which the compound of formula (I) is a compound corresponding to the following formula (II):

(II)

in which n, R ¹ , R ² and R ³ are as defined in formula (I).

The compounds of formula (II) correspond to compounds of formula (I) in which X ¹ =X ² =NH and R ⁴ =R ⁵ =NH ₂ .

Preferably, in formula (II), R ² and R ³ are identical.

According to one embodiment, in formula (II), n is equal to 1 or 2.

In the following, the compounds of formula (II) with n=1 may be designated "trimers", the compounds according to the invention with n=2 may be designated "pentamers", and the compounds according to the invention with n >2 can indifferently be designated “higher degree oligomers”. Higher degree oligomers include heptamers in particular.

The present invention also relates to a cosmetic composition as defined above, in which the compound of formula (I) is a compound corresponding to the following formula (III):

(III)

in which n, R ¹ and R ² are as defined above.

The compounds of formula (III) correspond to compounds of formula (I) in which X ¹ =X ² =NH, R ⁴ =R ⁵ =NH ₂ and R ² and R ³ are identical.

Preferably, in formula (III), R ² represents a divalent, linear or branched alkylene radical, comprising from 34 to 36 carbon atoms.

Advantageously, a compound of formula (I), or even of formula (III), according to the invention can be qualified as a polyamide.

Preferably, a hair cosmetic composition according to the invention comprises at least one compound of formula as defined below:

Compound of formula (I)

A composition according to the invention may comprise compounds of formula (I) which differ in that:

- the groups R ² and R ³ are different within the same compound of formula (I); and or

- R groups¹,R²,R³,R⁴and or R⁵are different between two compounds of formula (I).

A preferred hair cosmetic composition according to the invention comprises at least two different compounds corresponding to formula (I) as defined above.

According to a preferred embodiment, the hair cosmetic composition according to the invention comprises at least one compound of formula (I) in which n=1 and at least one compound of formula (I) in which n=2.

According to one embodiment, the hair cosmetic composition as defined above further comprises at least one compound of formula H ₂ NR ² -NH ₂ , R ² being as defined above in formula (I).

The present invention also relates to a hair cosmetic composition as defined above, comprising from 0.1% to 20%, preferably from 0.5% to 15%, and preferably from 1% to 10%, by weight of compound. (s) of formula (I) relative to the total weight of the oily phase, or even of said hair cosmetic composition.

The present invention also relates to a hair cosmetic composition as defined above, comprising from 10% to 99.9%, preferably from 20% to 90%, better still from 30% to 85%, and in particular from 50% to 90%. 80%, by weight of oil(s) relative to the total weight of the oily phase, or even of said hair cosmetic composition.

Oils)

Advantageously, the fatty phase may comprise at least one oil.

By “oil” we mean a liquid fatty substance at room temperature and atmospheric pressure.

As oils according to the invention, we can cite for example:

- hydrocarbon oils of plant origin, as described below;

- hydrocarbon oils of animal origin, such as perhydrosqualene and squalane;

- synthetic esters and ethers, in particular of fatty acids, such as oils of formulas R ₁ COOR ₂ and R ₁ OR ₂ in which R ₁ represents the remainder of a C ₈ to C ₂₉ fatty acid, and R ₂ represents a hydrocarbon chain, branched or not, at C ₃ to C ₃₀ , such as for example Purcellin oil, isononyl isononanoate, isodecyl neopentanoate, isostearyl neopentanoate, isopropyl myristate , octyldodecyl myristate, 2-ethylhexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetrabehenate (DUB PTB) or pentaerythrityl tetraisostearate (Prisorin 3631);

- linear or branched hydrocarbons, of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parléam oil;

- fatty alcohols having 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), or even octyldodecanol;

- and their mixtures.

Preferably, the fatty phase of a composition according to the invention comprises at least one vegetable oil.

As hydrocarbon oil(s) of plant origin, mention may be made of caprylic and capric acid triglycerides, caprylic and capric acid triglycerides (also known as "MCT oil"), myristic and stearic (INCI name: Caprylic/capric/myristic/stearic Triglyceride), triethylhexanoin, meadowfoam seed oil Limnanthes Alba (INCI name: Limnanthes Alba (Meadowfoam) Seed Oil), macadamia nut oil ( INCI name: Macadamia Ternifolia Seed Oil), Rosa Canina rosehip oil (INCI name: Rosa Canina Fruit Oil), soybean oil (INCI name: Glycine Soja (Soybean) Oil), sunflower (INCI name: Helianthus Annuus (Sunflower) Seed Oil), tribehenin (INCI name: tribehenin), triisostearin (INCI name: triisostearin), apricot kernel oil (INCI name: Prunus Armeniaca (Apricot) Kernel Oil), rice bran oil (INCI name: Oryza Sativa (Rice) Bran Oil), argan oil (INCI name: Argania Spinosa Kernel Oil), avocado oil (INCI name: Persea Gratissima Oil), evening primrose oil (INCI name: Oenothera Biennis Oil), rice germ oil (INCI name: Oryza Sativa Germ Oil), hydrogenated coconut oil (INCI name: Hydrogenated Coconut Oil), sweet almond oil (INCI name: Prunus Amygdalus Dulcis Oil), sesame seed oil (INCI name: Sesamum Indicum Seed Oil), hydrogenated rapeseed oil (INCI name: Hydrogenated Rapeseed Oil ), safflower seed oil (INCI name: Carthamus Tinctorius Seed Oil), Queensland Macadamia integrifolia walnut oil (INCI name: Macadamia Integrifolia Seed Oil), tricaprylin (or triacylglycerol), germ oil wheat (INCI name: Triticum Vulgare Germ Oil), borage seed oil (INCI name: Borago Officinalis Seed Oil), shea oil (INCI name: Butyrospermum Parkii Oil), hydrogenated castor oil ( INCI name: Hydrogenated Castor Oil), Chinese cabbage seed oil (INCI name: Brassica Campestris Seed Oil), camellia oil, and in particular Japanese camellia seed (INCI name: Camellia Japonica Seed Oil), green tea seed oil (INCI name: Camellia Sinensis Seed Oil), sea buckthorn oil (INCI name: Hippophae Rhamnoides Oil), Camellia Kissi seed oil (INCI name: Camellia Kissi Seed Oil) , Moringa seed oil (INCI name: Moringa Pterygosperma Seed Oil), canola oil (INCI name: Canola Oil), tea seed oil (INCI name: Camellia Oleifera Seed Oil), carrot seed oil (INCI name: Daucus Carota Sativa Seed Oil), triheptanoin (INCI name: Triheptanoin), vanilla oil (INCI name: Vanilla Planifolia Fruit Oil), canola oil glycerides and phytosterols (INCI name: Phytosteryl Canola Glycerides), blackcurrant seed oil (INCI name: Ribes Nigrum (Black Currant) Seed Oil), karanja seed oil (INCI name: Pongamia Glabra Seed Oil), oil achiote (INCI name: Roucou (Bixa orellana) Oil), baobab oil, jojoba oil and mixtures thereof, and particularly argan oil, castor oil, baobab oil , coconut oil, jojoba oil, and mixtures thereof.

Advantageously, the fatty phase of a composition according to the invention comprises at least one, or even at least two, oil(s), preferably chosen from hydrocarbon oil(s) of plant origin. , and preferably chosen from meadowfoam seed oil Limnanthes Alba (INCI name: Limnanthes Alba (Meadowfoam) Seed Oil, caprylic and capric acid triglycerides, and their mixture.

A composition according to the invention may comprise between 1% and 95%, preferably between 5% and 90%, in particular between 10% and 80%, or even between 20% and 70%, by weight of oil(s) of silicone and/or fluorinated oil(s), in particular silicone oil(s), relative to the total weight of the fatty phase, or even of the composition.

Preferably, a composition according to the invention comprises a content of less than 50%, preferably less than 25%, in particular less than 10%, or even less than 5%, and better still less than 1%, or even does not include, d silicone oil(s) and/or fluorinated oil(s), in particular silicone oil(s), relative to the total weight of the fatty phase, or even of the composition.

Lipophilic gelling agent(s)

According to one embodiment, the fatty phase further comprises at least one lipophilic gelling agent.

Such a gelling agent is different from the cationic polymers and oils described above, as well as the anionic polymers described later.

In the context of the invention, and unless otherwise stated, the term "gelling agent" means an agent making it possible to increase the viscosity of the fatty phase of the dispersion devoid of said gelling agent, and to achieve, for example, a final viscosity of the gelled fatty phase greater than 20,000 mPa.s, preferably greater than 50,000 mPa.s, better still greater than 100,000 mPa.s, and most particularly greater than 200,000 mPa.s.

Preferably, the lipophilic gelling agent according to the invention is chosen from organic or mineral, polymeric or molecular lipophilic gelling agents; fatty substances solid at ambient temperature and pressure, in particular chosen from waxes, pasty fatty substances, butters, and mixtures thereof; and their mixtures.

These lipophilic gelling agents are described in more detail in WO2021234135.

According to a preferred embodiment, the lipophilic gelling agent is chosen from the group consisting of polymeric lipophilic gelling agents, and in particular chosen from the group consisting of polyacrylates, esters of dextrin and fatty acid(s), esters of glycerol and fatty acid(s), polyamides, and mixtures thereof.

We can in particular cite esters of dextrin and fatty acid(s) marketed under the names Rheopearl® KL2 (INCI name: dextrin palmitate), Rheopearl® TT2 (INCI name: dextrin palmitate ethylhexanoate), and Rheopearl® MKL2 (INCI name : dextrin myristate) by the company Miyoshi Europe.

According to a particularly preferred embodiment, the lipophilic gelling agent is chosen from Castor Oil/IPDI Copolymer (and) Caprylic/Capric Triglyceride, in particular marketed under the name Estogel M by PolymerExpert, Hydrogenated Castor Oil/Sebacic Acid Copolymer as well as that its derivatives, in particular marketed respectively under the names Estogel Green (or Estogel G) and Estogel Green 40 by PolymerExpert, Caprylic/Capric Triglyceride (and) Polyurethane-79, in particular marketed under the name OILKEMIA™ 5S polymer by the company Lubrizol, the Trihydroxystearin, notably marketed under the name THIXCIN® R by the company Elementis Specialties, and their mixtures, and better still Castor Oil/IPDI Copolymer (and) Caprylic/Capric Triglyceride.

As waxes, we can in particular cite ceresin, paraffin, ozokerite, polyethylene waxes, illipe butter, beeswax, carnauba wax, microcrystalline wax, lanolin, derivatives lanolin, candelilla wax, cocoa butter, shellac wax, spermaceti, bran wax, capok wax, sugar cane wax, montan wax, whale wax, berry wax, acacia flower wax, vegetable waxes, uricuria wax or Japanese wax, and mixtures thereof.

According to a particular embodiment, a composition according to the invention, in particular the fatty phase, does not comprise an elastomer gel comprising at least one dimethicone, in particular as sold by NuSil Technology under the name CareSil™ CXG-1104 ( INCI: Dimethicone (and) Dimethicone/Vinyl Dimethicone Crosspolymer).

Advantageously, a lipophilic gelling agent is a thermosensitive gelling agent, namely which reacts to heat, and in particular is a gelling agent which is solid at room temperature and liquid at a temperature above 50°C, preferably above 60°C, and better above 70°C. Preferably, a thermosensitive lipophilic gelling agent according to the invention has a melting point of between 50°C and 130°C, and preferably between 60°C and 120°C.

Advantageously, a fatty phase gelling agent according to the invention is a thixotropic gelling agent or capable of giving the solution which comprises it a thixotropic behavior. Such a thixotropic gelling agent is in particular chosen from fumed silicas optionally hydrophobically treated, described above.

Those skilled in the art will take care to choose the lipophilic gelling agent(s) and/or their quantity so as to (i) ensure that the advantageous properties of the composition according to the invention are not or substantially not altered by the addition envisaged and (ii) satisfy the constraints imposed by the manufacturing process implemented for the manufacture of the composition according to the invention. These adjustments are within the knowledge of those skilled in the art.

According to one embodiment, a hair cosmetic composition according to the present invention comprises from 0.5% to 30%, preferably from 1% to 25%, in particular from 1.5% to 20%, better still from 2% to 15%. %, and very particularly from 5% to 12%, by weight of lipophilic gelling agent(s) relative to the total weight of the oily phase, or even of said hair cosmetic composition.

Aqueous phase

According to one embodiment, the hair cosmetic composition according to the invention further comprises at least one aqueous phase.

According to one embodiment, the hair cosmetic composition according to the invention is in the form of an emulsion. It can therefore also include at least one aqueous phase.

According to one embodiment, the hair cosmetic composition according to the invention is a simple or multiple, direct or inverse emulsion.

When the composition is in the form of an emulsion, the fatty phase and the aqueous phase of the composition according to the invention are immiscible with each other at room temperature and atmospheric pressure. Thus, the solubility of the fatty phase in the aqueous phase is advantageously less than 5% by weight, and vice versa.

A composition according to the invention may also comprise at least two oily phases immiscible with each other, at least one of the two oily phases, or even the two oily phases, comprising at least one compound of formula (I) as described above.

Pairs of oils that are immiscible with each other are described in particular in application FR3063893.

According to a first embodiment, a composition according to the invention is in the form of a simple emulsion, that is to say containing only an aqueous phase and a fatty phase. Considering the nature of the phases, it can then be an oil-in-water type emulsion (or direct emulsion) or a water-in-oil type emulsion (or inverse emulsion).

According to a first embodiment, in the compositions of the invention, the fatty phase is the continuous phase and the aqueous phase is the dispersed phase.

According to a second embodiment, in the compositions of the invention, the fatty phase is the dispersed phase and the aqueous phase is the continuous phase, preferably in gel form.

According to another embodiment, a composition according to the invention is in the form of a multiple emulsion, in particular a double emulsion, for example of the water-in-oil-in-water, oil-in-water-in-water type. oil or oil-in-oil-in-water.

In other words, a hair cosmetic composition according to the invention can be a simple or multiple, direct or inverse emulsion.

According to a first embodiment, a composition according to the invention in emulsion form can be prepared according to a simple “non-microfluidic” process, namely by simple emulsification.

As in a classic emulsion, an aqueous solution and a fatty solution are prepared separately. For example, it is the addition with stirring of the fatty phase into the aqueous phase which creates the direct emulsion.

The viscosity of the phases, particularly of the continuous phase, and the shear force applied to the mixture are the two main parameters that influence the size and monodispersity of the dispersed oil phase drops.

According to a second embodiment, a composition according to the invention in emulsion form can also be prepared according to a microfluidic process, in particular as described in WO2012/120043, WO2015/055748 or WO2019145424.

Whatever the embodiment, a composition according to the invention in the form of an emulsion may comprise a dispersed phase of which all or part of the drops are macroscopic, that is to say visible to the naked eye. Thus, such a composition according to the invention can advantageously be described as a macroscopically inhomogeneous mixture of at least two immiscible phases. In other words, in such an emulsion according to the invention, the continuous phase can be advantageously individualized from the dispersed phase, and vice versa, in particular with the naked eye.

When a composition according to the invention is in the form of an emulsion, said composition may comprise between 1% and 90%, preferably between 5% and 80%, in particular between 10% and 70%, or even between 15% and 60%, and very particularly between 20% and 50%, by weight of aqueous phase relative to the total weight of the composition.

When a composition according to the invention is in the form of an emulsion, said composition may comprise between 10% and 99%, preferably between 15% and 90%, in particular between 20% and 80%, or even between 30% and 70%, and particularly between 40% and 60%, by weight of fatty phase relative to the total weight of the composition.

Other ingredients

The hair cosmetic composition according to the invention may also comprise at least one compound chosen from:

- at least one anionic polymer, in particular hydrophilic anionic polymer, preferably a carbomer;

- at least one surfactant;

- at least fixing polymer, in particular those listed in applications FR2964565 or US2013289080;

- at least one conditioning agent (or “conditioning agent”), in particular chosen from a cationic conditioning agent;

- at least one hydrophilic thickening agent;

- at least one fatty substance different from the oils and lipophilic gelling agents mentioned above;

- at least one polysaccharide, in particular chitosans or their derivatives;

- at least one anti-UV agent;

- at least one filler such as mother-of-pearl, titanium dioxide, resins or clays;

- at least one perfume or perfuming agent;

- at least one peptizing agent;

- at least one vitamin;

- at least one curator;

- at least one acidic agent;

- at least one alkaline agent;

- at least one reducing agent;

- at least one oxidizing agent;

- at least one direct dye or one oxidation dye;

- at least one additional compound as described below;

- at least at least biological and/or cosmetic active ingredient; And

- their mixtures.

According to one embodiment, the hair cosmetic composition according to the present invention further comprises at least one anionic polymer.

Preferably, the anionic polymer is a hydrophilic polymer capable of being ionized.

By "anionic type chemical function", we mean a chemical function AH capable of giving up a proton to give a function A ^- . Depending on the conditions of the environment in which it is found, the anionic type polymer therefore comprises chemical functions in AH form, or in the form of its conjugated base A ^- .

As an example of chemical functions of anionic type, we can cite the carboxylic acid functions –COOH, possibly present in the form of carboxylate anion –COO ^- .

As an example of an anionic type polymer, mention may be made of any polymer formed by the polymerization of monomers of which at least one part carries anionic type chemical functions, such as carboxylic acid functions. Such monomers are for example acrylic acid, maleic acid, or any ethylenically unsaturated monomer comprising at least one carboxylic acid function. It may for example be an anionic polymer comprising monomer units comprising at least one chemical function of the carboxylic acid type.

Preferably, the anionic polymer is hydrophilic, that is to say soluble or dispersible in water.

Among the examples of anionic type polymer suitable for the implementation of the invention, mention may be made of copolymers of acrylic acid or maleic acid and other monomers, such as acrylamide, alkyl acrylates , C ₅ -C ₈ alkyl acrylates, C ₁₀ -C ₃₀ alkyl acrylates, C ₁₂ -C ₂₂ alkyl methacrylates, methoxypolyethylene glycol methacrylates, hydroxyester acrylates, crosspolymer acrylates , and their mixtures.

According to the invention, an anionic type polymer is preferably a carbomer as described below. This polymer can also be a crosslinked acrylates/C ₁₀ - ₃₀ alkyl acrylate copolymer (INCI name: acrylates/C ₁₀ - ₃₀ alkyl acrylate Crosspolvymer).

According to one embodiment, the anionic polymer is a polymer comprising monomer units comprising at least one carboxylic acid chemical function, preferably chosen from carbomers or a crosslinked acrylates/C ₁₀ - ₃₀ alkyl acrylate copolymer, and preferably a carbomer.

In the context of the invention, and unless otherwise stated, the term "carbomer" means a possibly crosslinked homopolymer, resulting from the polymerization of acrylic acid. It is therefore a poly(acrylic acid) possibly crosslinked. Among the carbomers of the invention, we can cite those marketed under the names Tego ^® Carbomer 340FD from Evonik, Carbopol ^® 981 from Lubrizol, Carbopol ETD 2050 from Lubrizol, or even Carbopol Ultrez 10 from Lubrizol.

According to one embodiment, the term "carbomer" or "carbomer" or "Carbopol ^® " means a high molecular weight acrylic acid polymer crosslinked with allylic sucrose or allylic ethers of pentaerythritol (handbook of Pharmaceutical Excipients, 5 ^th Edition, plll). For example, these are Carbopol ^® 910, Carbopol ^® 934, Carbopol ^® 934P, Carbopol ^® 940, Carbopol ® 941, Carbopol ^® 71G, ^{Carbopol ® 980} , Carbopol ^® 971P or Carbopol ^® 974P . According to one embodiment, the viscosity of said carbomer is between 4,000 and 60,000 cP at 0.5% w/w.

Carbomers have other names: polyacrylic acids, carboxyvinyl polymers or carboxy polyethylenes.

According to the invention, the compositions according to the invention may comprise a carbomer and a crosslinked acrylates/C ₁₀ - ₃₀ alkyl acrylate copolymer.

The aqueous phase according to the invention may also comprise at least one crosslinked polymer or at least one crosslinked copolymer, said crosslinked polymer or crosslinked copolymer comprising at least one unit derived from the polymerization of one of the following monomers: acrylic or methacrylic acid, acrylate or alkyl methacrylate comprising from 1 to 30 carbon atoms, or their salts.

The aqueous phase may also comprise a mixture of crosslinked polymers or a mixture of crosslinked copolymers or even a mixture of crosslinked polymer(s) and crosslinked copolymer(s).

According to the invention, the term "unit derived from the polymerization of a monomer" means that the polymer or copolymer is a polymer or copolymer obtained by polymerization or copolymer of said monomer.

According to one embodiment, the crosslinked polymer or the crosslinked copolymer is a crosslinked polyacrylate.

The copolymers and crosslinked polymers of the invention are anionic.

According to one embodiment, the copolymer is a copolymer of unsaturated carboxylic acid and of unsaturated C _1-30 alkyl carboxylate, preferably C ₁ -C ₄ alkyl. Such a copolymer comprises at least one hydrophilic unit of the olefinic unsaturated carboxylic acid type and at least one hydrophobic unit of the (C ₁ -C ₃₀ ) alkyl ester type of unsaturated carboxylic acid.

Preferably, these copolymers are chosen from those whose hydrophilic unit of unsaturated olefinic carboxylic acid type corresponds to the monomer of formula (IV) following:

in which: R ₁ denotes H or CH ₃ or C ₂ H ₅ , that is to say acrylic acid, methacrylic acid or ethacrylic acid units, and whose hydrophobic unit of alkyl ester type (C ₁ -C ₃₀ ) of unsaturated carboxylic acid corresponds to the monomer of formula (V) following:

in which: R ₂ designates H or CH ₃ or C ₂ H ₅ (that is to say acrylate, methacrylate or ethacrylate units) and preferably H (acrylate units) or CH ₃ (methacrylate units), R ₃ designating a C ₁ -C ₃₀ , and preferably C ₁ -C ₄ , alkyl radical.

Among this type of copolymers, those formed from a mixture of monomers comprising:

(i) primarily acrylic acid,

(ii) an ester of formula (IV) described above and in which R ₂ designates H or CH ₃ , R ₃ designating an alkyl radical having 1 to 4 carbon atoms,

(iii) and a crosslinking agent, which is a well-known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, trimethylolpropane tri(meth)acrylate, diallyl itaconate, diallyl fumarate, diallyl maleate, zinc (meth)acrylate, (meth) )allyl acrylate, divinylbenzene, (poly)ethylene glycol dimethacrylate, methylene-bis-acrylamide, and castor oil.

According to one embodiment, the crosslinked polymer or the crosslinked copolymer is a polymer or copolymer of acrylic acid and/or methacrylic acid, and/or alkyl acrylate comprising from 1 to 30 carbon atoms, preferably from 1 to 4 carbon atoms, and/or alkyl methacrylate comprising from 1 to 30 carbon atoms, preferably from 1 to 4 carbon atoms.

According to one embodiment, the crosslinked copolymer is a crosslinked copolymer of methacrylic acid and alkyl acrylate comprising from 1 to 4 carbon atoms, preferably 2 carbon atoms.

In the context of the invention, and unless otherwise stated, the term “crosslinked copolymer of methacrylic acid and alkyl acrylate comprising from 1 to 4 carbon atoms” means a crosslinked copolymer resulting from the polymerization of a methacrylic acid monomer and an alkyl acrylate monomer comprising from 1 to 4 carbon atoms.

Preferably, in this copolymer, the methacrylic acid represents from 20% to 80% by weight, preferably from 35% to 65% by weight of the total weight of the copolymer.

Preferably, in this copolymer, the alkyl acrylate represents from 15% to 80% by weight, preferably from 35% to 65% by weight of the total weight of the copolymer.

In particular, the alkyl acrylate is chosen from alkyl methacrylate, ethyl acrylate and butyl acrylate.

According to one embodiment, the crosslinked polymer or the crosslinked copolymer according to the invention, present in the continuous aqueous phase, is chosen from the group consisting of the following polymers or copolymers: Acrylates Copolymer, Acrylates crosspolymer-4, Acrylates crosspolymer-3, Polyacrylate-2 Crosspolymer and Polyacrylate-14 (INCI names).

Among said polymers above, we particularly prefer, according to the present invention, the products sold by the company LUBRIZOL under the trade names Fixate Superhold (INCI name = Polyacrylate-2 Crosspolymer), Fixate Freestyle Polymer (INCI name = Acrylates crosspolymer- 3), Carbopol ^® Aqua SF1 (INCI name = Acrylates copolymer) and Carbopol ^® Aqua SF2 (INCI name = Acrylates crosspolymer-4).

Preferably, the crosslinked copolymer is Carbopol ^® Aqua SF1 (INCI name = Acrylates copolymer).

According to one embodiment, the crosslinked copolymer is chosen from crosslinked copolymers of acrylic or methacrylic acid and alkyl acrylates comprising from 1 to 4 carbon atoms.

According to the invention, the compositions according to the invention may comprise a carbomer and a crosslinked copolymer Carbopol ^® Aqua SF1 (INCI name = Acrylates copolymer).

According to one embodiment, the hair cosmetic composition according to the invention further comprises at least one surfactant, in particular a cationic, nonionic, anionic, amphoteric surfactant, and their mixtures. Such surfactants are chosen from those commonly used for hair compositions.

As hydrophilic thickening agents, we can cite those described in WO2021234135. Mention may in particular be made of polysaccharides, homopolymers or copolymers based on carboxylic acid or carboxylate, polyquaternium compounds, polyvinylpyrrolidone (PVP) polymers, sucrose esters, polygylceryl esters and mixtures thereof. More particularly, the thickening agent is chosen from hydroxypropyl guar, xanthan gum, guar gum, biosaccharide gum, cellulose, acacia seneca gum, sclerotium gum, agarose, pectin, gellan gum, hyaluronic acid and a mixture thereof.

As a conditioning agent, we can cite for example amidoamine compounds.

Examples of amidoamines which are useful in compositions according to the invention include, but are not limited to the following: oleamidopropyl dimethylamine, stearamidopropyl dimethylamine, isostearamidopropyl dimethylamine, stearamidoethyl dimethylamine, lauramidopropyl dimethylamine, myristamidopropyl dimethylamine, behenamidopropyl dimethylamine, dilinoleamidopropyl dimethylamine , palmitamidopropyl dimethylamine, ricinoleamidopropyl dimethylamine, soyamidopropyl dimethylamine, wheat germamidopropyl dimethylamine, sunsolamidopropyl dimethylamine, almondamidopropyl dimethylamine, avocadoamidopropyl dimethylamine, babassuamidopropyl dimethylamine, cocamidopropyl dimethylamine, visonamidopropyl dimethylamine, oatsamidopropyl dimethylamine, sesamidopropyl dimethylamine, tallamidopropyl dimethylamine, brass icamidopropyl dimethylamine, olivamidopropyl dimethylamine, palmitamidopropyl dimethylamine, stearamidoethylamine, and mixtures thereof.

In certain other embodiments, the cationic conditioning agents may be selected from monoalkyl quaternary amines, dialkyl quaternary amines or polyquaternium compounds or their salts.

For example, the cationic conditioning agents may be chosen from Polyquaterium-10 (also called quaternized polyhydroxyethylcellulose), cetrimonium chloride, behentrimonium chloride, behentrimonium methosulfate, steartrimonium chloride, stearalkonium chloride, chloride dicetyldimonium, hydroxypropyltrimonium chloride, cocotrimonium methosulfate, olealkonium chloride, steartrimonium chloride, babassuamidopropalkonium chloride, brassicamidopropyl dimethylamine, Quaternium-91, Polyquaternium-37 (for example under the brand SALCARE), Quaternium -22, Quaternium-87, Polyquaternium-4, Polyquaternium-6, Polyquaternium-11, Polyquaternium-44, Polyquaternium-67, Amodimethicone, Lauryl Betaine, Polyacrylate-1 Crosspolymer, Steardimonium Hydroxypropyl Hydrolyzed Wheat Protein, Behenamidopropyl PG-dimonium Chloride , lauryldimonium hydroxypropyl hydrolyzed soy protein, aminopropyl dimethicone, Quaternium-8, and dilinoleamidopropyl dimethylamine PEG-7 phosphate, and mixtures thereof.

In certain embodiments, the cationic polymers can be chosen for example from the following: polyquaternium 4, polyquaternium 6, polyquaternium 7, polyquaternium 10, polyquaternium 11, polyquaternium 16, polyquaternium 22, polyquaternium 28, polyquaternium 32, polyquaternium-46, polyquaternium -51, polyquaternium-52, polyquaternium-53, polyquaternium-54, polyquaternium-55, polyquaternium-56, polyquaternium-57, polyquaternium-58, polyquaternium-59, polyquaternium-60, polyquaternium-63, polyquaternium-64, polyquaternium-65 , polyquaternium-66, polyquaternium-67, polyquaternium-70, polyquaternium-73, polyquaternium-74, polyquaternium-75, polyquaternium-76, polyquaternium-77, polyquaternium-78, polyquaternium-79, polyquaternium-80, polyquaternium-81 , polyquaternium -82, polyquaternium-84, polyquaternium-85, polyquaternium-86, polyquaternium-87, polyquaternium-90, polyquaternium-91, polyquaternium-92, polyquaternium-94, or guar hydroxypropyltrimonium chloride, and mixtures thereof.

According to one embodiment, the cationic conditioning agent is chosen from Polyquaternium-67, Polyquaternium-10, Polyquaternium-37, or mixtures thereof. For example, Polyquaternium-37 is commercially available from BASF under the brand name SALCARE SC 96 (comprising Polyquaternium-37 (and) Propylene Glycol Dicaprylate/Dicaprate (and) PPG-1 Trideceth-6), and mixtures thereof.

As fatty substances, we can cite for example fatty alcohols, fatty esters, fatty acids, their derivatives or a mixture of these. More specifically, the fatty substance is:

- a fatty ester chosen from cetyl ester, purcellin oil (cetearyl octanoate), isopropyl myristate, isopropyl palmitate, C12-C15 alkyl benzoate, 2-ethylphenyl benzoate , isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, oleyl erucate, 2-ethylhexyl palmitate, isostearyl isostearate, isostearyl sebacate diisopropyl, octanoates, decanoates or ricinoleates of alcohols or polyalcohols, hydroxylated esters and pentaerythritol esters, and mixtures thereof;

- a fatty alcohol chosen from decyl alcohol, undecyl alcohol, dodecyl alcohol, myristyl alcohol, lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol (cetyl alcohol and stearyl alcohol), isostearyl alcohol, isocetyl alcohol, behenyl alcohol, linalool, oleyl alcohol, cis-4-t-butylcyclohexanol, isotridecyl alcohol, myricylic alcohol and mixtures thereof;

- a polyol chosen from ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, pentylene glycol, diethylene glycol, dipropylene glycol, caprylyl glycol, 1,3-propanediol, glycerol, diglycerol, polyethylene glycols, and mixtures thereof; And

- their mixtures.

A composition according to the invention, in particular the fatty phase and/or the aqueous phase (when present), may also comprise at least one additional compound different from the cationic and anionic polymers, lipophilic gelling agents and oils mentioned above ( e)s.

The compositions according to the invention can thus also comprise powders; Glitter ; coloring agents, in particular chosen from water-soluble or not, fat-soluble or not, organic or inorganic coloring agents, materials with an optical effect, liquid crystals, and mixtures thereof; particulate agents insoluble in the fatty phase; fillers, of an organic or mineral nature; conservatives; humectants; stabilizers; chelators; emollients; modifying agents chosen from texture agents (or gelling agents), pH, osmotic force and/or refractive index modifiers, etc. or any usual cosmetic additive for hair compounds; and their mixtures.

Also, the compositions according to the invention may further comprise at least one biological and/or cosmetic active ingredient chosen from moisturizing agents, healing agents, depigmenting agents, UV filters, desquamating agents, antioxidant agents, stimulating active ingredients. the synthesis of dermal and/or epidermal macromolecules, dermodecontracting agents, antiperspirant agents, soothing agents, anti-aging agents, perfuming agents, anticoagulants, anti-thrombogenic agents, anti-mitotic agents, anti-proliferation, anti-adhesion, anti-migration, cell adhesion promoters, growth factors, antiparasitic molecules, anti-inflammatories, angiogenics, angiogenesis inhibitors, vitamins, hormones, proteins, antifungals, antimicrobial molecules, antiseptics or antibiotics and their mixtures. Such assets are described in particular in FR 1 558 849.

Of course, those skilled in the art will take care to choose any other ingredient(s) mentioned above and/or their quantity in such a way that the advantageous properties of the composition according to the invention are not or substantially not altered by the addition envisaged. Also, those skilled in the art will take care to choose the nature and/or quantity of other ingredient(s) depending on the aqueous or fatty nature of the phase considered and/or with regard to the dispersion manufacturing process. .

These adjustments fall within the general knowledge of those skilled in the art.

Uses

As indicated above, the present invention relates to a hair cosmetic composition, intended in particular for the treatment and/or care of keratin fibers, in particular hair.

The hair cosmetic compositions may comprise, in addition to the aforementioned ingredients, at least one physiologically acceptable medium.

In the context of the invention, and unless otherwise stated, the term "physiologically acceptable medium" means a medium suitable for cosmetic applications, and suitable in particular for the application of a composition of the invention to a keratin material, in particular the hair.

The physiologically acceptable medium is generally adapted to the nature of the support on which the composition must be applied, as well as to the aspect in which the composition must be packaged.

According to one embodiment, the physiologically acceptable medium is represented directly by the aqueous continuous phase as described above.

Among the cosmetic compositions according to the invention, mention may be made, for example, of a hair care product (hair dyes and bleaches), a cleaning product (lotions, powders, shampoos), a hair care product (lotions, creams). , oils) or a styling product (lotions, hairspray, brilliantines).

The present invention also relates to the use of a compound of formula (I) as defined above, or of a hair cosmetic composition as defined above, for the care and/or cosmetic treatment of keratin fibers, in particular hair, and in particular to make it easier to comb, make the hair more docile, make it softer to the touch, make it more lustrous, coat the hair fiber, form a thin film around the hair shaft and the skin; improve the lengthening of hair curls; and/or protect and maintain color vibrancy.

The present invention also relates to a non-therapeutic cosmetic process for the care and/or treatment of keratin fibers, in particular hair, in which an effective quantity of the hair cosmetic composition according to the invention is applied to the keratin fibers.

Throughout the description, the expression “comprising one” must be understood as being synonymous with “comprising at least one”, unless the contrary is specified. The expressions “between… and…”, “between… and…” and “ranging from… to…” must be understood inclusive, unless otherwise specified.

The examples which follow illustrate the present invention without limiting its scope.

EXAMPLES

Example 1 – Synthesis of a cationic polymer according to the invention

This example 1 is based on the use of a first raw material marketed by Croda under the name Priamine 1075.

Priamine 1075 Property Unit Value Amine index mgKOH/g 205 Color Gardner 1 Dynamic viscosity mPa.s at 25ºC 210 ISCC PLUS certified sustainable bio-content % 100

This example 1 is based on the use of a second raw material marketed by Croda under the name Pripol 1009:

Pripol 1009 Property Unit Value Acid number mgKOH/g 196 APHA color Hazen at 25ºC 50 Iodine index mgKOH/g 7 ISCC PLUS certified sustainable bio-content % 100

The purification solvent used is Cetiol® C5C (INCI: Coco-Caprylate/Caprate) marketed by the company BASF.

Step 1 – synthesis:

546g of Priamine 1075 and 142g of Pripol 1009 are introduced into a 1L reactor. The reaction mixture is left under mechanical stirring at 140° C. for 23 hours under vacuum. The reaction is monitored by infrared, in particular by increase and stabilization of the peak linked to the amide functions (CONH, 1646 cm ^-1 ). Size exclusion chromatography (CES) in polystyrene calibration indicates in the reaction product the presence of 44% of Priamine (theoretical Mn 546g/mol), 35% of trimers (theoretical Mn 1663g/mol), 15% of pentamers (Mn theoretical 2780g/mol), and 6% of higher degree oligomers. The amine number of the reaction medium is measured by titration at 2.2 equivalents/kg.

Step 2 – purification:

10g of reaction crude obtained from step 1 and 90g of Cetiol® C5C are mixed. The mixture is centrifuged at 5000 rpm, at 15°C, for 15 minutes then placed at 4°C overnight. The mixture is then recentrifuged at 5000 rpm, at 4°C, for 15 to 20 minutes. The pellet containing Priamine (30%), trimers (37%), pentamers (20%) and higher degree oligomers (13%) is eliminated. The percentage evaluated by gravimetry of compound(s) of formula (I) in solution in the oil is approximately 8.2% and its composition estimated by calculation is 38% of Priamine, 42% of trimers, 14% of pentamers and 6% higher degree oligomers. The amine index “compounds of formula (I)/Cetiol® C5C” measured by titration is 0.205eq/kg.

Compound of formula (I) resulting from the reaction between
Priamine 1075 and Pripol 1009

Example 2 – Preparation of a hair cosmetic composition ( shampoo )

Phase INCI DESIGNATION 1A
(comparative) 1B
(comparative) 1 C
(invention) w/w% HAS Water QSP* QSP* QSP* HAS Sodium laureth sulfate Genapol LRO 25.00 25.00 25.00 HAS Glycerin 1.00 1.00 1.00 B Polysorbate-20 Eumulgin SML 20 0.50 0.50 0.50 B Cetrimonium Chloride Dehyquart A-CA 0.10 0.10 0.10 B Oleamide DEA Comperlan OD V 0.50 0.50 0.50 VS Cocamidopropyl Betaine Genagen CAB 818 15.00 15.00 15.00 VS Hydrolysis Keratin - 0.25 0.25 0.25 VS Fragrance - 1.00 1.00 1.00 VS Condom agent Euxyl K900 0.50 0.50 0.50 D Amodimethicone CAS-3131 0 0.3 0 D Compound according to Example 1 - 0 0 0.15 D Coco-Caprylate/Caprate Cetiol C5C 1.9 1.9 1.9 E Sodium Chloride - 1.20 1.20 1.20 Total 100 100 100

* QSP: Sufficient Quantity For.

Protocol :

The ingredients of phase A are mixed (mixture A) and the ingredients of phase B are mixed (mixture B).

Mixture B is added to mixture A with stirring until homogenized (mixture AB).

Mixture C is added to mixture AB with stirring until homogenized (mixture ABC).

Mixture D is added to mixture ABC with stirring until homogenized (mixture ABCD).

Phase E is added to the ABCD mixture with stirring until homogenization (final mixture).

Assessment

Compositions 1A, 1B and 1C are then used by a panel of 24 women between 22 and 45 years old in shampoo application.

With compositions 1B and 1C, improved properties are observed compared to composition 1A in terms of foaming, detangling and shine of the hair.

Furthermore, we observe that compositions 1B and 1C have similar properties in terms of foaming, detangling and hair shine.

Example 3 – Preparation of a hair cosmetic composition (conditioner)

Phase DESIGNATION INCI SUPPLIER 2A
(comp.) 2B
(comp.) 2C
(inv.) % HAS DEIONIZED WATER aqua/water - QSP* QSP* QSP* HAS MICROCARE NB sodium benzoate THOR 0.50 0.50 0.50 HAS ULTRAGEL 300 polyquaternium-37 FRIEND 0.30 0.30 0.30 HAS GLYCERIN glycerin INTERCHEMISTRY 3.00 3.00 3.00 B DEHYQUART C4046 Cetearyl Alcohol (and)
Dipalmitoylethyl Hydroxyethylmonium Methosulfate
(and) Ceteareth-20 FRIEND 9.00 9.00 9.00 B LANETTE 16 Cetyl alcohol FRIEND 3.00 3.00 3.00 B MANGO BUTTER Mango butter SOPHIM 1.00 1.00 1.00 B ACAI OIL Euterpe Oleracea (Acai) Fruit Oil LAVOLLEE 1.00 1.00 1.00 B CRODAMOL SS Cetyl Esters CRODA 3.00 3.00 3.00 VS SCENT Fragrance 0.50 0.50 0.50 VS DEHYQUART A/CA Cetrimonium chloride FRIEND 5.00 5.00 5.00 D AMANDULINE HC Hydrolyzed Sweet Almond Seedcake SILAB 1.00 1.00 1.00 D HELIOGENOL Butylene Glycol (and) Helianthus Annuus (Sunflower) Seed Extract SEDERMA 0.70 0.70 0.70 D NUTELINE C PS Hydrolyzed hazelnut protein SOLIANCE 1.00 1.00 1.00 E CAS-3131 Amodimethicone NUSIL 0 1.00 0 E Compound according to Example 1 - - 0 0 0.5 E Cetiol C5C Coco-Caprylate/Caprate BASF 5.00 5.00 5.00 F CITRIC ACID Citric acid PRODHYG 1.00 1.00 1.00 Total 100.00 100.00 100.00

* QSP: Sufficient Quantity For.

Protocol :

The ingredients of phase A are mixed (mixture A) and the ingredients of phase B are mixed (mixture B).

Mixture B is added to mixture A with stirring until homogenized (mixture AB).

Mixture C is added to mixture AB with stirring until homogenized (mixture ABC).

Mixture D is added to mixture ABC with stirring until homogenized (mixture ABCD).

Mixture E is added to mixture ABCD with stirring until homogenized (mixture ABCDE).

Phase F is added to the ABCDE mixture with stirring until homogenization (final mixture).

Assessment

Compositions 2A, 2B and 2C are then used by a panel of 24 women between 22 and 45 years old in conditioner application.

With compositions 2B and 2C, improved properties are observed compared to composition 2A in terms of detangling properties, styling, external/aesthetic appearance of the hair and shine of the hair.

Furthermore, we observe that compositions 2B and 2C have similar properties in terms of detangling, styling, external/aesthetic appearance of the hair and shine of the hair.

Example 4 – Preparation of a hair cosmetic composition (serum)

DESIGNATION SUPPLIERS INCI NAME 3A
(comp.) 3B
(comp.) 3C
(inv.) % CALSIL CB10 CALDIC Cyclopentasiloxane(and) Dimethiconol QSP* QSP* QSP* CALSIL V50 CALDIC Cyclopentasiloxane 21.00 21.00 21.00 SESAME OIL PRODHYG Sesamum Indicum Seed Oil 1.00 1.00 1.00 KAHAI OIL DKSH Caryodendron Orinosense Seed Oil 2.00 1.00 1.00 CAS-3131 NUSIL Amodimethicone 0 6.00 0 Compound of Example 1 - - 0 0 2 Cetiol C5C BASF Coco-Caprylate/Caprate 16.50 16.50 16.50 BRAZIL PERFUME VOX Perfume/fragrance 1.00 1.00 1.00 TOTAL 100.00 100.00 100.00

* QSP: Sufficient Quantity For.

Assessment

Compositions 3A, 3B and 3C are then used by a panel of 24 women between 22 and 45 years old in hair care application.

With compositions 3B and 3C, improved properties are observed compared to composition 3A in terms of external appearance/aesthetics of the hair and shine of the hair.

Furthermore, it is observed that compositions 3B and 3C have similar properties in terms of external appearance/aesthetics of the hair and shine of the hair.

CONCLUSION :

It emerges from Examples 2, 3 and 4 above that a compound of formula (I) according to the invention presents itself as a completely satisfactory non-silicone alternative to amodimethicone, particularly in the context of the formulation of cosmetic compositions, particularly hair compositions.

A compound of formula (I) according to the invention therefore presents itself as a credible biosourced alternative to silicone compounds, and in particular to amodimethicone, particularly for use in hair.

Furthermore, the similarities in terms of hair effects between amodimethicone and the compound of formula (I) are obtained with quantities of compound of formula (I) lower than the quantities of amodimethicone, which is very unexpected.

Claims (18)

Hair cosmetic composition, in particular for the treatment and/or care of keratin fibers, in particular hair, comprising at least one oily phase and at least one compound of formula (I) below:
(I)
in which :

• n is an integer comprised from 1 to 5, preferably comprised from 1 to 3, preferably equal to 1 or 2,
• X ¹ and X ² , identical or different, represent ^, independently of each other, -O-, -CH ₂ - or -NH-, preferably at least ^one of the groups X ¹ and X ² , representing -NH-,
• R ¹ , R ² and R ³ , identical or different, independently represent a divalent, linear, cyclic or branched alkylene radical, comprising from 20 to 50 carbon atoms, preferably from 25 to 45 carbon atoms, better still from 30 to 40 carbon atoms, and preferably from 34 to 36 carbon atoms, R ¹ , R ² and R ³ being able to include a cycloalkylene radical comprising 3 to 10 carbon atoms, preferably comprising 6 carbon atoms, said radical cycloalkylene being optionally substituted by one or more alkyl chains comprising from 6 to 10 carbon atoms,
• R ⁴ and R ⁵ , identical or different, represent, independently of each other, H, OH or NH ₂ , at least one of the groups R ⁴ and R ⁵ representing NH ₂ .

Hair cosmetic composition according to claim 1, in which, in formula (I), in which X ¹ and X ² represent -NH-. Hair cosmetic composition according to claim 1 or 2, comprising at least one compound of formula (I) in which R ⁴ and R ⁵ represent NH ₂ . Hair cosmetic composition according to any one of the preceding claims, in which the compound of formula (I) is a compound corresponding to the following formula (II):
(II)
in which n, R ¹ , R ² and R ³ are as defined in claim 1, R ² and R ³ preferably being identical. Cosmetic composition according to any one of the preceding claims, in which the compound of formula (I) is a compound corresponding to the following formula (III):
(III)
in which n, R ¹ and R ² are as defined in claim 1. Hair cosmetic composition according to any one of the preceding claims, comprising at least two different compounds corresponding to formula (I). Hair cosmetic composition according to any one of the preceding claims, comprising at least one compound of formula (I) in which n=1 and at least one compound of formula (I) in which n=2. Hair cosmetic composition according to claim 7, further comprising at least one compound of formula H ₂ NR ² -NH ₂ , R ² being as defined in claim 1. Hair cosmetic composition according to any one of the preceding claims, comprising from 0.1% to 20%, preferably from 0.5% to 15%, and preferably from 1% to 10%, by weight of compound(s) of formula (I) relative to the total weight of the oily phase, or even of said hair cosmetic composition. Hair cosmetic composition according to any one of the preceding claims, comprising from 10% to 99.9%, preferably from 20% to 90%, better still from 30% to 85%, and in particular from 50% to 80%, in weight of oil(s) relative to the total weight of the oily phase, or even of said hair cosmetic composition. Hair cosmetic composition according to any one of the preceding claims, in which the oily phase comprises at least one lipophilic gelling agent, preferably chosen from organic or mineral, polymeric or molecular lipophilic gelling agents; solid fatty substances at ambient temperature and pressure; and their mixtures. Hair cosmetic composition according to the preceding claim, comprising from 0.5% to 30%, preferably from 1% to 25%, in particular from 1.5% to 20%, better still from 2% to 15%, and very particularly from 5% to 12%, by weight of lipophilic gelling agent(s) relative to the total weight of the oily phase, or even of said hair cosmetic composition. Hair cosmetic composition according to any one of the preceding claims, further comprising at least one aqueous phase. Hair cosmetic composition according to the preceding claim, characterized in that said composition is a simple or multiple, direct or inverse emulsion. Hair cosmetic composition according to any one of the preceding claims, further comprising at least one compound chosen from:
- at least one anionic polymer, in particular hydrophilic anionic polymer, and preferably a carbomer;
- at least one surfactant;
- at least fixing polymer;
- at least one conditioning agent, in particular chosen from a cationic conditioning agent;
- at least one hydrophilic thickening agent;
- at least one fatty substance;
- at least one polysaccharide, in particular chitosans or their derivatives;
- at least one anti-UV agent;
- at least one filler such as mother-of-pearl, titanium dioxide, resins or clays;
- at least one perfuming agent;
- at least one peptizing agent;
- at least one vitamin;
- at least one curator;
- at least one acidic agent;
- at least one alkaline agent;
- at least one reducing agent;
- at least one oxidizing agent;
- at least one direct dye or one oxidation dye;
- at least at least biological and/or cosmetic active ingredient; And
- their mixtures. Hair cosmetic composition according to any one of the preceding claims, further comprising at least one surfactant, in particular a cationic, nonionic, anionic, amphoteric surfactant, and mixtures thereof. Use of a compound of formula (I) as defined in any one of claims 1 to 9, or of a composition according to any one of claims 1 to 16, for the care and/or cosmetic treatment of keratin fibers, especially hair. Non-therapeutic cosmetic process for the care and/or treatment of keratin fibers, in particular hair, in which an effective quantity of the composition according to any one of claims 1 to 16 is applied to the keratin fibers.