FR3127124A1 - Composition comprising cysteine and a particular fatty acid triglyceride - Google Patents

Abstract

Composition comprising cysteine and a particular fatty acid triglyceride The present invention relates to a composition useful for styling and/or conditioning keratinous fibres, and in particular human keratinous fibers such as the hair, which comprises cysteine and /or one of its derivatives and a particular fatty acid triglyceride. The invention also relates to a cosmetic process for styling and/or conditioning keratinous fibers using such a composition. Figure for abstract: NONE

Description

Composition comprising cysteine and a particular fatty acid triglyceride

The present invention relates to a composition useful for styling and/or conditioning keratinous fibres, and in particular human keratinous fibers such as the hair, which comprises cysteine and/or a derivative thereof and a fatty acid triglyceride particular.

The invention also relates to a cosmetic process for styling and/or conditioning keratinous fibers using such a composition.

Many people are unhappy with the way their hair looks and find it difficult to style it. Curly hair is particularly difficult to comb and detangle, which takes a lot of time and effort for a result that is disappointing most of the time.

In addition, the hair is generally damaged and weakened by the action of external atmospheric agents such as lighting and bad weather, but also by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching , perms and/or straightening. The hair is therefore damaged by these different factors and can, over time, become dry, rough or dull, especially in fragile areas.

Thus, to overcome these drawbacks, it is customary to use care compositions which condition the hair in an appropriate manner, by giving it satisfactory conditioning properties, in particular in terms of smoothness, shine, softness, suppleness, lightness , natural feel and good detangling properties.

These hair care compositions can be, for example, conditioning shampoos, hair conditioners, masks or serums, and can be in the form of gels, hair lotions or more or less thick care creams. These compositions can be rinse-off compositions or leave-on compositions.

These compositions generally comprise a combination of cationic conditioning agents such as cationic surfactants, cationic polymers, silicones and/or fatty substances, such as fatty alcohols, in order to give the hair satisfactory cosmetic properties, in particular in terms of softness, smooth character and suppleness.

However, these conditioning agents, and in particular the fatty alcohols, often have the disadvantage of making the hair very soft and heavy, which leads to the phenomenon commonly called "dullness". In other words, fatty alcohols are deposited in large quantities on the hair, which has the effect of making it soft, greasy and dull.

Nevertheless, the elimination or reduction of these fatty substances decreases the conditioning effects, and therefore the conditioning properties of the hair.

Most of these compositions also include silicones. Indeed, these compounds are known to improve the cosmetic properties of the hair, in particular in terms of smoothness and flexibility (as shown in documents JP 48 (1973) -19941, JP 56 (1986) -92808, and US 5,374,421 ). However, several disadvantages remain. For example, hair treated with these compositions remains limp and sticky, and may exhibit poor combability.

There is therefore a real need to develop compositions which do not have the disadvantages described above, that is to say which are capable of improving the conditioning properties of the hair, in particular in terms of combability when dry and when dry. wet state, suppleness, smoothness, manageability and shine, without overloading the hair or causing a greasy feel or look.

The compositions should also improve the combing, styling and detangling properties of hair, particularly curly to frizzy hair, while reducing tangles and preventing fiber breakage or damage.

It has now been discovered that a composition, comprising cysteine and/or one of its derivatives in combination with a particular fatty acid triglyceride, makes it possible to achieve the objectives described above. In particular, it has been found that hair treated with such a combination is easier to comb and detangle and has better conditioning properties, especially in terms of smoothness, suppleness and shine. The hair is also more manageable leading to better styling, and exhibits less breakage. These benefits are also sustainable.

Thus, the subject of the invention is in particular a composition comprising:

(i) cysteine and/or one of its derivatives such as N-acetylcysteine, an N-alkanoylcysteine and the alkyl esters of cysteine,

(ii) one or more fatty acid triglycerides containing from 6 to 16 carbon atoms in a total amount greater than or equal to 1% by weight, relative to the total weight of the cosmetic composition;

the pH of said composition ranging from 7.5 to 10, and

said composition being free of additional reducing agent other than cysteine and/or one of its derivatives (i).

The composition of the present invention is capable of improving the conditioning properties of keratinous fibers, in particular human keratinous fibers such as the hair, in particular in terms of shine, softness, smoothness and suppleness while giving the hair good combability at dry and wet, as well as improved handling.

The hair, in particular curly hair, thus treated with the composition of the present invention is easier to comb and allows the consumer to obtain the desired hairstyle.

The composition of the present invention also respects the integrity of the fibers and provides a better moisturizing effect. Hair is also healthier and stronger, making it more resistant to combing and detangling.

The invention also relates to a cosmetic process for styling and/or conditioning keratinous fibres, in particular human keratinous fibers such as the hair, which consists in applying to said keratinous fibers a composition as defined previously, and after a laying optional, optionally to be removed by rinsing.

Other subjects, characteristics, aspects and advantages of the invention will appear even more clearly on reading the description and the example which follow.

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

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

(i) Cysteine

The composition according to the present invention comprises cysteine and/or one of its derivatives such as N-acetylcysteine, an N-alkanoylcysteine and the alkyl esters of cysteine.

The total quantity of cysteine and/or one of its derivatives such as N-acetylcysteine, an N-alkanoylcysteine and the alkyl esters of cysteine, present in the composition according to the present invention, is preferably less than or equal to 1% by weight, more preferably this total amount ranges from 0.05 to 1% by weight, even more preferably from 0.1 to 1% by weight, and even more preferably from 0.5 to 0.8% by weight, relative to the total weight of the composition.

The composition according to the present invention is free of additional reducing agent other than cysteine or its derivatives (i).

Within the meaning of the present invention, the expression “additional reducing agent” encompasses thiol reducing agents different from cysteine or its derivatives (i) and non-thiol reducing agents.

The expression “thiol reducing agent” designates a reducing agent containing at least one thiol group. Examples of thiol reducing agent(s) other than cysteine or its derivatives (i) correspond to thioglycolic acid and its derivatives, in particular its esters such as glycerol or glycol monothioglycolate; thiolactic acid and its derivatives, in particular its esters such as glycerol monothiolactate; 3-mercaptopropionic acid and its derivatives, in particular its esters such as glycerol 3-mercaptopropionate and ethylene glycol 3-mercaptopropionate; cysteamine and its derivatives, in particular its C1-4 acyl derivatives such as N-acetylcysteamine and N-propionylcysteamine; mono-thioglycerol and its derivatives, in particular its esters; and their salts.

The term "non-thiol reducing agent" means a reducing agent which does not contain a thiol group. Examples of non-thiol reducing agent(s) are sulphites, bisulphites, sulfinates, phosphines, sugars, dihydroxybenzene derivatives, reductones and hydrides.

Within the meaning of the present invention, the term "free of" refers to a composition which does not contain (0%) an additional reducing agent other than cysteine or its derivatives (i) or which contains less than 0.1% by weight of additional reducing agents, relative to the total weight of the composition.

(ii) Fatty Acid Triglyceride

The composition according to the present invention further comprises one or more triglyceride(s) of fatty acid (ii) containing from 6 to 16 carbon atoms.

The useful fatty acid triglyceride(s) according to the present invention may be derived from triglycerides of plant origin, such as vegetable oils, or from triglycerides of synthetic origin.

Preferably, the fatty acid triglyceride(s) contain from 6 to 14 carbon atoms, and more preferably from 6 to 12 carbon atoms.

Preferably, the vegetable oils that can be used according to the invention comprise more than 50% by weight of triglyceride(s) of fatty acids containing from 6 to 16 carbon atoms, preferably from 6 to 14, more preferably from 6 to 12 carbon atoms. of carbon.

Advantageously, the fatty acid triglyceride(s) are chosen from coconut oil, caprylic/capric acid triglycerides, palm kernel oil, babasu oil, cuphea oil and mixtures thereof.

The total quantity of triglyceride(s) of fatty acid (ii) containing from 6 to 16 carbon atoms, which are present in the composition according to the present invention, is greater than or equal to 1% by weight, relative to the total weight of composition. Preferably, the total amount of triglyceride(s) of fatty acids (ii) containing from 6 to 16 carbon atoms ranges from 1 to 15% by weight, and more preferably from 2 to 10% by weight, relative to the weight composition total.

The weight ratio (R) between the total quantity of triglyceride(s) of fatty acid(s) (ii) containing from 6 to 16 and the total quantity of cysteine and/or one of its derivatives (i), present in the composition according to the present invention, is preferably greater than or equal to 1. More preferably, this weight ratio (R) is between 1 and 20, and better still between 2 and 15.

Additional fatty substances

The composition according to the present invention may also comprise one or more additional fatty substances, different from the fatty acid triglycerides (ii) previously described.

The term "fatty substance" means an organic compound that is insoluble in water at ordinary temperature (25° C.) and at atmospheric pressure (760 mmHg) (solubility less than 5%, preferably less than 1% and even more preferably less than 0.1%). They carry in their structure at least one hydrocarbon chain including at least 6 carbon atoms or a sequence of at least two siloxane groups. In addition, fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for example chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF) , liquid petroleum jelly or decamethylcyclopentasiloxane.

Preferably, the fatty substances of the invention do not contain any salified or non-salified carboxylic acid groups (-C(O)OH or -C(O)O-). In particular, the fatty substances of the invention are neither polyoxyalkylenated nor polyglycerolated.

The term “non-silicone fatty substance” designates a fatty substance containing no silicon (Si) atom and the term “silicone fatty substance” designates a fatty substance containing at least one silicon atom.

More particularly, the additional fatty substance(s), different from the triglyceride(s) of fatty acids containing from 6 to 16 carbon atoms, are chosen from C ₆ to C ₁₆ hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils of animal origin, triglycerides other than fatty acid triglycerides (ii) previously described, fluoro oils, non-polyoxyalkylenated fatty alcohols, esters of fatty acids and/or fatty alcohols other than triglycerides, vegetable waxes, non-silicone waxes, silicones and mixtures thereof.

It is recalled that, in the context of the invention, fatty alcohols, fatty esters and fatty acids more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon groups, comprising 6 to 30 carbon atoms, optionally substituted , in particular, by one or more (in particular 1 to 4) hydroxyl groups. If unsaturated, these compounds can have one to three conjugated or unconjugated carbon-carbon double bonds.

As regards the C ₆ to C ₁₆ hydrocarbons, they are linear, branched or optionally cyclic, and are preferably alkanes. Examples which may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.

One hydrocarbon oil of animal origin that may be mentioned is perhydrosqualene.

The triglyceride different from the fatty acid triglyceride (ii) containing from 6 to 16 carbon atoms is preferably chosen from liquid fatty acid triglycerides containing from 18 to 30 carbon atoms, for example sunflower oil, corn oil, soybean oil, pumpkin oil, rapeseed oil, grapeseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, jojoba oil, and mixtures thereof.

The linear or branched hydrocarbons of mineral or synthetic origin, containing more than 16 carbon atoms, are preferably chosen from liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes and hydrogenated polyisobutene such as Parleam® .

The fluoro oils can be chosen from perfluoromethylcyclopentane and perfluoro-1,3-dimethylcyclohexane, sold under the names Flutec® PC1 and Flutec® PC3 by the company BNFL Fluorochemicals; perfluoro-1,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050® and PF 5060® by the company 3M, or alternatively bromoperfluorooctyle sold under the name Foralkyl® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethylperfluoromorpholine sold under the name PF 5052® by the company 3M.

The non-polyoxyalkylenated fatty alcohols which can be used in the composition according to the invention are saturated or unsaturated, and linear or branched, and include from 8 to 30 carbon atoms and more particularly from 10 to 24 carbon atoms. Examples include cetyl alcohol, stearyl alcohol and mixtures thereof (cetyl stearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol and linoleyl alcohol.

The wax or waxes which can be used in the composition according to the invention are chosen in particular from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, vegetable waxes, for example olive wax, rice wax, hydrogenated jojoba wax or absolute flower waxes such as the essential blackcurrant flower wax sold by Bertin (France), animal waxes, for example beeswax , or modified beeswax (cerabellina); other waxes or waxy raw materials that can be used according to the invention are in particular marine waxes such as the product sold by the company Sophim under the reference M82, and polyethylene or polyolefin waxes in general.

As regards the esters of fatty acids and/or of fatty alcohols, which are advantageously different from the triglycerides mentioned above, mention may be made in particular of the esters of C ₁ to C ₂₆ aliphatic mono- or polyacids, saturated or unsaturated, linear or branched, and aliphatic C ₁ to C ₂₆ mono- or polyalcohols, saturated or unsaturated, linear or branched, the total carbon number of the esters being more particularly greater than or equal to 10.

Among the monoesters, mention may be made of dihydroabietyl behenate; octyldodecyl behenate; isocetyl behenate; cetyl lactate; C ₁₂ -C ₁₅ alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methyl acetyl ricinoleate; myristyl stearate; octyl isononanoate; 2-ethylhexyl isononanoate; octyl palmitate; octyl pelargonate; octyl stearate; octyldodecyl erucate; oleyl erucate; ethyl and isopropyl palmitates, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl, 2-octyldodecyl, myristyl or stearyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate.

Still in the context of this variant, it is also possible to use esters of C ₄ to C ₂₂ dicarboxylic or tricarboxylic acids and of C ₁ to C ₂₂ alcohols, as well as esters of mono-, di- or tricarboxylic acids and C ₂ to C ₂₆ di-, tri-, tetra- or pentahydroxyalcohols.

Mention may in particular be made of: diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate; propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; propylene glycol dioctanoate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate; polyethylene glycol distearates.

Among the esters mentioned above, use is preferably made of ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as myristate d isopropyl, butyl, cetyl or 2-octyldodecyl, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isonyl isononanoate or cetyl octanoate.

The composition may also comprise, as fatty ester, sugar esters and diesters of C ₆ to C ₃₀ and preferably C ₁₂ to C ₂₂ fatty acids. It is recalled that the term “sugar” designates oxygenated hydrocarbon compounds which comprise several alcohol functions, with or without aldehyde or ketone functions, and which include at least 4 carbon atoms. These sugars can be monosaccharides, oligosaccharides or polysaccharides.

Examples of suitable sugars which may be mentioned include sucrose (or sucrose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, in particular alkyl derivatives, such as derivatives methyl, for example methylglucose.

The sugar esters of fatty acids can be chosen in particular from the group comprising the esters or mixtures of esters of sugars described above and of linear or branched, saturated or unsaturated, C ₆ to C 30 and preferably C 6 to C ₃₀ fatty acids. _C12 to _C22 . If unsaturated, these compounds may have one to three conjugated or unconjugated carbon-carbon double bonds.

The esters according to this alternative form can also be chosen from mono-, di-, tri- and tetraesters and polyesters, and mixtures thereof.

These esters can be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates or arachidonates, or mixtures thereof such as, in particular, mixed oleate/palmitate, oleate/stearate or palmitate/stearate.

More particularly, mono- and diesters are used and in particular mono- or di-oleate, -stearate, -behenate, -oleate/palmitate, -linoleate, -linolenate or -oleate/stearate of sucrose, glucose or methylglucose.

Mention may be made, by way of example, of the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.

Examples of fatty acid sugar esters or mixtures of sugar esters which may also be mentioned include:

- the products sold under the names F160, F140, F110, F90, F70 and SL40 by the company Crodesta, respectively designating sucrose palmitates/stearates formed of 73% monoester and 27% di- and triester, 61% monoester and 39% di-, tri- and tetraester, 52% monoester and 48% di-, tri- and tetraester, 45% monoester and 55% di-, tri- and tetraester, and 39% monoester and 61 % di-, tri- and tetraester, and sucrose monolaurate;

- the products sold under the name Ryoto Sugar Esters, for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% diester, triester and polyester;

- mono-dipalmitate/sucrose stearate sold by the company Goldschmidt under the name Tegosoft® PSE.

The silicones that can be used according to the invention can be in the form of oils, waxes, resins or gums.

Preferably, the silicone is chosen from polydialkylsiloxanes, in particular polydimethylsiloxanes (PDMS), and organomodified polysiloxanes including at least one functional group chosen from amino groups, aryl groups and alkoxy groups.

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

When they are volatile, the silicones are more particularly chosen from those having a boiling point of between 60° C. and 260° C., and more particularly still from:

(I) cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms. These include, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide, and Silbione® 70045 V5 by Rhodia, and mixtures thereof.

Mention may also be made of cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, such as Volatile Silicone® FZ 3109 sold by the company Union Carbide, of formula:

Mention may also be made of mixtures of cyclic polydialkylsiloxanes with organosilicon compounds, such as the mixture of octamethylcyclotetrasiloxane and tetra(trimethylsilyl)pentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1'-bis (2,2,2',2',3,3'-hexatrimethylsilyloxy)neopentane;

(ii) volatile linear polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity less than or equal to 5×10 ^-6 m²/s at 25°C. An example is the decamethyltetrasiloxane sold in particular under the name SH 200 by the company Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, p. 27-32, Todd & Byers, “Volatile Silicone Fluids for Cosmetics”.

Non-volatile polydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with the above organofunctional groups, and mixtures thereof are preferably used.

These silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes carrying terminal trimethylsilyl groups. The viscosity of silicones is measured at 25°C according to the ASTM 445 Annex C standard.

Among these polydialkylsiloxanes, mention may be made, without limitation, of the following commercial products:

- Silbione oils from the 47 and 70 047 ranges or Mirasil oils marketed by Rhodia, for example oil 70 047 V 500 000,

- oils from the Mirasil® range sold by Rhodia;

- the oils of the 200 range from Dow Corning, such as DC200, the viscosity of which is 60,000 mm ² /s;

- Viscasil® oils from General Electric and certain oils of the SF range (SF 96, SF 18) from General Electric.

Mention may also be made of polydimethylsiloxanes containing dimethylsilanol end groups called dimethiconol (CTFA), such as the oils of the 48 range from Rhodia.

In this category of polydialkylsiloxanes, mention may also be made of the products sold under the names Abil Wax® 9800 and 9801 by the company Goldschmidt, which are poly(C ₁ -C ₂₀ )dialkylsiloxanes.

The silicone gums that can be used according to the invention are in particular polydialkylsiloxanes and preferably polydimethylsiloxanes having high number-average molecular weights, between 200,000 and 1,000,000, used alone or as a mixture in a solvent. This solvent can be chosen from volatile silicones, polydimethylsiloxane oils (PDMS), polyphenylmethylsiloxane oils (PPMS), isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.

The products which can be used more particularly according to the invention are mixtures such as:

- mixtures formed from a hydroxy-terminated polydimethylsiloxane or dimethiconol (CTFA), and a cyclic polydimethylsiloxane, also called cyclomethicone (CTFA), such as the product Q2 1401 sold by the company Dow Corning;

- mixtures of a polydimethylsiloxane gum and a cyclic silicone, such as the product SF 1214 Silicone Fluid from General Electric; this product is an SF 30 gum corresponding to a dimethicone, having a number-average molecular weight of 500,000, dissolved in SF 1202 Silicone Fluid oil corresponding to decamethylcyclopentasiloxane;

- mixtures of two PDMS of different viscosities, and more particularly of a PDMS gum and a PDMS oil, such as the product SF 1236 from General Electric. The SF 1236 product is a mixture of an SE 30 rubber defined above, with a viscosity of 20 m²/s and an SF 96 oil with a viscosity of 5×10 ^-6 m²/s. This product preferably comprises 15% SE 30 gum. This product preferably includes 15% SE 30 gum and 85% of an SF 96 oil.

The organopolysiloxane resins that can be used according to the invention are crosslinked siloxane systems containing the following units:

R ₂ SiO _2/2 , R3SiO _1/2 , RSiO _3/2 and SiO _4/2 ,

in which R represents an alkyl containing 1 to 16 carbon atoms. Among these products, those which are particularly preferred are those in which R denotes a lower C ₁ -C ₄ alkyl group, more particularly methyl.

Among these resins, mention may be made of the product marketed under the name Dow Corning 593 or those marketed under the name Silicone Fluid SS 4230 and SS 4267 by General Electric, which are silicones with a dimethyl/trimethylsiloxane structure.

Mention may also be made of resins of the trimethylsiloxysilicate type, sold in particular under the references X22-4914, X21-5034 and X21-5037 by Shin-Etsu.

The organomodified silicones that can be used according to the invention are silicones as defined above and including in their structure one or more organofunctional groups attached via a hydrocarbon group.

The organomodified silicones can be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organofunctional groups mentioned above.

The polyalkylarylsiloxanes are chosen in particular from polydimethyl/methylphenylsiloxanes and linear and/or branched polydimethyl/diphenylsiloxanes, the viscosity of which is between 1×10 ^-5 and 5×10 ^-2 m ² /s at 25°C.

Among these polyalkylarylsiloxanes, mention may in particular be made of the products sold under the following names:

- Silbione® oils from the 70 641 range from Rhodia;

- oils from the Rhodorsil® 70 633 and 763 range from Rhodia;

- Dow Corning 556 Cosmetic Grade Fluid oil from Dow Corning;

- silicones from Bayer's PK range, such as the PK20 product;

- the silicones of the PN and PH range from Bayer, such as the PN1000 and PH1000 products;

- certain oils from General Electric's SF range, such as SF 1023, SF 1154, SF 1250 and SF 1265.

Among the organomodified silicones, mention may also be made of polyorganosiloxanes including:

- substituted or unsubstituted amino groups, such as the products sold under the names GP 4 Silicone Fluid and GP 7100 by the company Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning. Substituted amino groups are in particular C ₁ -C ₄ aminoalkyl groups;

- alkoxylated groups, such as the product sold under the name Silicone Copolymer F-755 by SWS Silicones and Abil Wax® 2428, 2434 and 2440 by the company Goldschmidt.

The silicones which can be used in the composition of the present invention can also be chosen from amino silicones.

The term “aminosilicone” designates any silicone including at least one primary, secondary or tertiary amine or a quaternary ammonium group.

The weight-average molecular masses of these aminosilicones can be measured by gel permeation chromatography (CPG for “Chromatography Gel Permeation”) at ambient temperature (25° C.), in polystyrene equivalent. The columns used are styragel µ columns. The eluent is THF and the flow rate is 1 mL/min. 200 µL of a 0.5% by weight silicone solution in THF are injected. The detection is carried out by refractometry and by UV-metry.

Throughout the text below, the term “silicone” is intended to designate, according to what is generally accepted, any organosilicon polymer or oligomer of linear or cyclic, branched or cross-linked structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and formed essentially of a repetition of main units in which the silicon atoms are bonded together together with oxygen atoms (siloxane bond -Si-O-Si-), optionally substituted hydrocarbon groups being directly bonded by a carbon atom to said silicon atoms. The most common hydrocarbon groups are the alkyl groups, in particular the C ₁ -C ₁₀ alkyl groups and in particular the methyl, the fluoroalkyl groups whose alkyl part is in C ₁ -C ₁₀ , and the aryl groups and in particular the phenyl.

Suitable aminosilicones that can be used according to the present invention include, but are not limited to, volatile and non-volatile, cyclic, linear and branched aminosilicones, with a viscosity ranging from 5×10 ^-6 to 2.5 m ² /s at 25°C, for example from 1×10 ^-5 to 1 m ² /s.

Preferably, the aminosilicone(s) are chosen from:

a) the polysiloxanes corresponding to the formula (I):

in which x' and y' are whole numbers such that the weight-average molecular mass (Mw) is between 5,000 and 500,000 g/mole;

b) aminosilicones corresponding to formula (II):

R' _a G _3-a -Si(OSiG ₂ ) _n -(OSiG _b R' _2-b ) _m -O-SiG _3-a '-R'_a' (II)

in which :

- the Gs, which may be identical or different, represent a hydrogen atom, a phenyl, OH, C ₁ -C ₈ alkyl group, for example methyl, or C ₁ -C ₈ alkoxy, for example methoxy,

- a and a', which may be identical or different, represent 0 or an integer from 1 to 3, in particular 0, provided that at least one of a and a' is equal to zero,

- b represents 0 or 1, in particular 1,

- m and n are numbers such that the sum (n + m) is between 1 and 2000 and in particular between 50 and 150, n being able to designate a number from 0 to 1999 and in particular from 49 to 149, and m being able to designate a number from 1 to 2000 and in particular from 1 to 10; And

- the R', identical or different, denotes a monovalent radical of formula -C _q H2 _q L in which q is a number ranging from 2 to 8 and L is an optionally quaternized amino group chosen from the following groups:

-NR''-QN(R'') ₂ ,

-N(R'') ₂ ,

-N ⁺ (R'') ₃ A ^- ,

- N ⁺ H(R'') ₂ A ^- ,

- N ⁺ H ₂ (R'') A ^- ,

-NR''-Q- N ⁺ (R'')H ₂ A-,

-NR''-Q- N ⁺ (R'') ₂ HA ^- and

-NR''-Q- N ⁺ (R'') ₃ A ^- ,

in which R'', which may be identical or different, denote hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon radical, for example a C ₁ -C ₂₀ alkyl radical; Q denotes a linear or branched group of formula C _r H _2r , r being an integer ranging from 2 to 6, preferably from 2 to 4; and A ^- represents a cosmetically acceptable anion, in particular a halide such as fluoride, chloride, bromide or iodide.

According to a first embodiment, the aminosilicones corresponding to formula (II) are chosen from silicones called “trimethylsilyl amodimethicone”, corresponding to formula (III):

in which m and n are numbers such that the sum (n + m) is between 1 and 2000 and in particular between 50 and 150, n being able to designate a number from 0 to 1999 and in particular from 49 to 149, and m being able to designate a number from 1 to 2000 and in particular from 1 to 10.

According to a second embodiment, the aminosilicones corresponding to formula (II) are chosen from the silicones of formula (IV) below:

in which :

- m and n are numbers such that the sum (n+m) is between 1 and 1000, in particular between 50 and 250 and more particularly between 100 and 200; n designating a number from 0 to 999, in particular from 49 to 249 and more particularly from 125 to 175, and m designating a number from 1 to 1000, in particular from 1 to 10 and more particularly from 1 to 5; And

- R ₁ , R ₂ and R ₃ , which may be identical or different, represent a hydroxyl or C ₁ -C ₄ alkoxy radical, at least one of the radicals R ₁ to R ₃ denoting an alkoxy radical.

Preferably, the alkoxy radical is a methoxy radical.

The hydroxy/alkoxy molar ratio is preferably between 0.2:1 and 0.4:1, preferably between 0.25:1 and 0.35:1 and is more particularly equal to 0.3:1.

The weight-average molecular mass (Mw) of these silicones is preferably between 2,000 and 1,000,000 g/mol and more particularly between 3,500 and 200,000 g/mol.

According to a third embodiment, the aminosilicones corresponding to formula (II) are chosen from the silicones of formula (V) below:

in which :

- p and q are numbers such that the sum (p + q) is between 1 and 1000, in particular between 50 and 350 and more particularly between 150 and 250; p denoting a number from 0 to 999, in particular from 49 to 349 and more particularly from 159 to 239, and q denoting a number from 1 to 1000, in particular from 1 to 10 and more particularly from 1 to 5; And

- R ₁ and R ₂ , which are different, represent a hydroxyl or C ₁ -C ₄ alkoxy radical, at least one of the R ₁ or R ₂ radicals designating an alkoxy radical.

Preferably, the alkoxy radical is a methoxy radical.

The hydroxy/alkoxy molar ratio is generally between 1:0.8 and 1:1.1, preferably between 1:0.9 and 1:1 and more particularly is equal to 1:0.95.

The weight-average molecular mass (Mw) of the silicone is preferably between 2,000 and 200,000 g/mol, more preferably between 5,000 and 100,000 g/mol and in particular between 10,000 and 50,000 g/mol.

Commercial products comprising silicones of structure (IV) or (V) can include in their composition one or more other aminosilicones, the structure of which is different from formula (IV) or (V).

A product containing structure (IV) aminosilicones is sold by Wacker under the name Belsil® ADM 652.

A product containing structure (V) aminosilicones is sold by Wacker under the name Fluid WR 1300®. Another product containing structure (IV) aminosilicones is sold by Wacker under the name Belsil ADM LOG 1®.

When using these aminosilicones, a particularly advantageous embodiment consists in using them in the form of an oil-in-water emulsion. The oil-in-water emulsion may comprise one or more surfactants. The surfactants can be of any kind but are preferably cationic and/or nonionic. The number average size of the silicone particles in the emulsion is generally between 3 nm and 500 nanometers. More preferably, in particular as aminosilicones of formula (V), microemulsions are used whose mean particle size is between 5 nm and 60 nm (limits included) and more particularly between 10 nm and 50 nm (limits included). Thus, it is possible to use, according to the invention, the aminosilicone microemulsions of formula (V) sold under the names Finish CT 96 E® or SLM 28020® by the company Wacker.

According to a fourth embodiment, the aminosilicones corresponding to formula (II) are chosen from the silicones of formula (VI) below:

in which :

- m and n are numbers such that the sum (n + m) is between 1 and 2000 and in particular between 50 and 150, n designating a number from 0 to 1999 and in particular from 49 to 149, and m designating a number of 1 to 2000 and in particular from 1 to 10; And

- A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.

The weight-average molecular mass (Mw) of these aminosilicones is preferably between 2,000 and 1,000,000 g/mol and more particularly between 3,500 and 200,000 g/mol.

A silicone corresponding to this formula is, for example, Xiameter MEM 8299 emulsion from Dow Corning.

According to a fifth embodiment, the aminosilicones corresponding to formula (II) are chosen from the silicones of formula (VII) below:

in which :

- m and n are numbers such that the sum (n + m) is between 1 and 2000 and in particular between 50 and 150, n being able to designate a number from 0 to 1999 and in particular from 49 to 149, and m being able to designate a number from 1 to 2000 and in particular from 1 to 10; And

- A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably branched.

The weight-average molecular mass (Mw) of these aminosilicones is preferably between 500 and 1,000,000 g/mol and more particularly between 1,000 and 200,000 g/mol.

A silicone corresponding to this formula is, for example, DC2-8566 Amino Fluid from Dow Corning;

c) aminosilicones corresponding to the formula (VIII):

in which

- R ₅ represents a monovalent hydrocarbon radical containing from 1 to 18 carbon atoms, and in particular a C ₁ -C ₁₈ alkyl or C ₂ -C ₁₈ alkenyl radical, for example methyl;

- R ₆ represents a divalent hydrocarbon radical, in particular a C ₁ -C ₁₈ alkylene radical or a divalent C ₁ -C ₁₈ alkyleneoxy radical, for example C ₁ -C ₈ , connected to Si by an SiC bond;

- Q ^- is an anion such as a halide ion, in particular chloride, or an organic acid salt, in particular acetate;

- r represents an average statistical value ranging from 2 to 20 and in particular from 2 to 8; And

- s represents an average statistical value ranging from 20 to 200 and in particular from 20 to 50.

Such aminosilicones are described in particular in US Pat. No. 4,185,087.

d) quaternary ammonium silicones of formula (IX):

in which :

- R ₇ , which may be identical or different, represent a monovalent hydrocarbon radical comprising from 1 to 18 carbon atoms, and in particular a C ₁ -C ₁₈ alkyl radical, a C ₂ -C ₁₈ alkenyl radical or a cycle comprising 5 or 6 carbon atoms, for example methyl;

- R ₆ represents a divalent hydrocarbon radical, in particular a C ₁ -C ₁₈ alkylene radical or a divalent C ₁ -C ₁₈ alkyleneoxy radical, for example C ₁ -C ₈ , connected to Si by an SiC bond;

- R ₈ , which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon radical containing from 1 to 18 carbon atoms, and in particular a C ₁ -C ₁₈ alkyl radical, a C ₂ alkenyl substituent - C ₁₈ or an -R ₆ -NHCOR ₇ radical;

- X ^- is an anion such as a halide ion, in particular chloride, or an organic acid salt, in particular acetate; And

- r represents an average statistical value ranging from 2 to 200 and in particular from 5 to 100.

Such aminosilicones are described in particular in patent application EP-A 0 530 974.

e) aminosilicones of formula (X):

in which :

- R ₁ , R ₂ , R ₃ and R ₄ , which may be identical or different, denote a C ₁ -C ₄ alkyl radical or a phenyl group,

- R ₅ denotes a C ₁ -C ₄ alkyl radical or a hydroxyl group,

- n is an integer ranging from 1 to 5,

- m is an integer ranging from 1 to 5, and

- x is chosen such that the amine number is between 0.01 and 1 meq/g;

f) multiblock polyoxyalkylenated aminosilicones, of the (AB)n type, A being a polysiloxane block and B being a polyoxyalkylenated block including at least one amine group.

Said silicones are preferably formed of repeated units corresponding to the following general formulas:

[-(SiMe ₂ O) _x SiMe ₂ -RN(R'')-R'-O(C ₂ H ₄ O) _a (C ₃ H ₆ O) _b -R'-N(H)-R-]

or alternatively

[-(SiMe ₂ O) _x SiMe ₂ -RN(R'')-R'-O(C ₂ H ₄ O) _a (C ₃ H ₆ O) _b -]

in which :

- a is an integer greater than or equal to 1, preferably ranging from 5 to 200 and more particularly ranging from 10 to 100;

- b is an integer between 0 and 200, preferably between 4 and 100 and more particularly between 5 and 30;

- x is an integer ranging from 1 to 10,000 and more particularly from 10 to 5,000;

- R'' is a hydrogen atom or a methyl;

- the Rs, which may be identical or different, represent a divalent C ₂ -C ₁₂ hydrocarbon radical, linear or branched, optionally including one or more heteroatoms such as oxygen; preferably, the R's, which may be identical or different, denote an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical or a CH ₂ CH ₂ CH ₂ OCH ₂ CH(OH)CH ₂ - radical; preferably, R denotes a CH ₂ CH ₂ CH ₂ OCH ₂ CH(OH)CH ₂ - radical; And

- the R', which may be identical or different, represent a divalent C ₂ -C ₁₂ hydrocarbon radical, linear or branched, optionally including one or more heteroatoms such as oxygen; preferably, the R', which may be identical or different, denote an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical or a CH ₂ CH ₂ CH ₂ OCH ₂ CH(OH)CH _{2 -} radical. ; preferably, R' denotes -CH(CH ₃ )-CH ₂ -.

The siloxane blocks preferably represent 50% molar and 95% molar of the total weight of the silicone, more particularly from 70% molar to 85% molar.

The amine content is preferably between 0.02 and 0.5 meq/g of copolymer in solution at 30% in dipropylene glycol, more particularly between 0.05 and 0.2.

The weight-average molecular mass (Mw) of the silicone is preferably between 5,000 and 1,000,000 g/mol and more particularly between 10,000 and 200,000 g/mol.

Mention may in particular be made of the silicones sold under the name Silsoft A-843 or Silsoft A+ by Momentive.

g) aminosilicones of formulas (XI) and (XII):

in which :

- R, R' and R'', which may be identical or different, represent a C ₁ -C ₄ alkyl group or a hydroxyl group,

- A denotes a C ₃ alkylene radical; And

- m and n are numbers such that the weight-average molecular mass of the compound is between 5,000 and 500,000

in which :

- x and y are numbers ranging from 1 to 5000; preferably, x ranges from 10 to 2000 and more preferably from 100 to 1000; more preferably, y is from 1 to 100;

- R ₁ and R ₂ , which may be identical or different, preferably identical, denote a linear or branched, saturated or unsaturated alkyl group, comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and more preferably from 12 to 20 carbon atoms; And

- A denotes a linear or branched alkylene radical containing from 2 to 8 carbon atoms.

Preferably, A comprises from 3 to 6 carbon atoms, more preferentially 4 carbon atoms; preferably A is branched.

Mention may in particular be made of the following divalent groups:

-CH ₂ CH ₂ CH ₂ - and CH ₂ CH(CH ₃ )CH ₂ -.

Preferably, R ₁ and R ₂ are independent saturated linear alkyl groups comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and in particular from 12 to 20 carbon atoms; particular mention may be made of dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; and preferably, R1 and R2, which may be the same or different, are chosen from hexadecyl (cetyl) and octadecyl (stearyl) groups.

The aminosilicone(s) are preferably of formula (XII) with:

- x ranging from 10 to 2000 and in particular from 100 to 1000;

- y ranging from 1 to 100;

- A comprising from 3 to 6 carbon atoms and in particular 4 carbon atoms; preferably A is branched; more particularly, A is chosen from the following divalent groups: -CH ₂ CH ₂ CH ₂ - and CH ₂ CH(CH ₃ )CH ₂ -; And

- R ₁ and R ₂ being independently saturated linear alkyl groups comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and in particular from 12 to 20 carbon atoms; chosen in particular from dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups; preferably, R ₁ and R ₂ , which may be identical or different, are chosen from hexadecyl (cetyl) and octadecyl (stearyl) groups.

A preferred silicone of formula (XII) is bis-cetearyl amodimethicone. Mention may be made in particular of the aminosilicone sold under the name Silsoft AX by Momentive.

h) polysiloxanes and in particular polydimethylsiloxanes, including primary amine groups only at the end of the chain or on the side chains, such as those of formula (XIV), (XV) or (XVI):

Or

Or

In formula (XIV), the values of n and m are such that the weight average molecular mass of the aminosilicone is between 1000 and 55,000.

As examples of aminosilicones of formula (XIV), mention may be made of the products sold under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203 by the company Gelest and KF-8015 by the Shin-Etsu company.

In formula (XV), the values of n and m are such that the weight average molecular mass of the aminosilicone is between 500 and 3000.

As examples of aminosilicones of formula (XV), mention may be made of the products sold under the names MCR-A11 and MCR-A12 by the company Gelest.

In formula (XVI), the values of n and m are such that the weight average molecular mass of the aminosilicone is between 500 and 50,000.

As examples of aminosilicones of formula (XVI), mention may be made of aminopropyl phenyl trimethicone sold under the name DC 2-2078 Fluid by the company Dow Corning.

i) and mixtures thereof.

Preferably, the aminosilicone(s) are chosen from aminosilicones of formulas (II), (XII) and (XVI) and mixtures thereof, more preferably chosen from aminosilicones of formula (XII), and mixtures thereof, and better still the aminosilicone (b) is bis-cetearyl amodimethicone.

Preferably, the additional fatty substance(s), different from fatty acid triglycerides (ii) containing from 6 to 16 carbon atoms, are chosen from fatty alcohols, fatty esters, vegetable oils of triglyceride type different from fatty acid triglycerides fatty (ii), aminosilicones and mixtures thereof.

The total amount of additional fatty substance(s), other than triglycerides of fatty acids (ii) containing from 6 to 16 carbon atoms, when present in the composition according to invention, is preferably between 0.5 and 20% by weight, and more preferably between 1 and 15% by weight, more preferably between 1.5 and 10% by weight relative to the total weight of the composition.

The total quantity of fatty substances (i.e. the sum of the total quantity of triglyceride(s) of fatty acid(s) (ii) containing from 6 to 16 carbon atoms and the total quantity of fatty substance optional additional fat(s), present in the composition according to the present invention, is preferably between 1 and 35% by weight, and more preferably between 5 and 25% by weight, by relative to the total weight of the composition.

The weight ratio (Ra) between the total amount of the additional fatty substance(s), other than fatty acid triglycerides (ii) containing 6 to 16 carbon atoms, and the total amount of fatty acid triglycerides (ii) containing from 6 to 16 carbon atoms is preferably greater than or equal to 1, more preferably greater than or equal to 1.5, and better still greater than or equal to 2.

Cationic surfactants

The composition according to the present invention may also comprise one or more cationic surfactant(s).

By "cationic surfactant" is meant a surfactant which is positively charged when it is contained in the composition according to the invention. This surfactant can bear one or more permanent positive charges or can contain one or more cationizable functions in the composition according to the invention.

The cationic surfactant(s) are preferably chosen from optionally polyoxyalkylenated primary, secondary or tertiary fatty amines, or their salts, and quaternary ammonium salts, and mixtures thereof.

The fatty amines generally comprise at least one C ₈ to C ₃₀ hydrocarbon chain.

The cationic surfactant(s) which can be used in the composition of the present invention are preferably chosen from the following quaternary ammonium salts and mixtures thereof:

- quaternary ammonium salts corresponding to the general formula (XVII) below:

(XVII)

in which the groups R ₂₈ to R ₃₁ , which may be identical or different, represent an aliphatic group, linear or branched, comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, one at minus the groups R ₂₈ to R ₃₁ designating a group comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms, the aliphatic groups can comprise heteroatoms such as in particular oxygen, nitrogen, sulfur and halogens. The aliphatic groups are chosen, for example, from C ₁ to C ₃₀ alkyl, C ₁ to C ₃₀ alkoxy, C ₂ to C ₆ polyoxyalkylene, C 1 to C ₃₀ alkylamide, C ₂ to C ₂ alkylamido C ₁₂ to C _{22 6} , C ₁₂ to C ₂₂ alkyl acetate, C ₁ to C ₃₀ hydroxyalkyl; X ⁻ is an anion chosen from the group of halides, phosphates, acetates, lactates, C ₁ to C ₄ alkyl sulphates, C ₁ to C ₄ alkylaryl sulphonates or C ₁ to C ₄ alkylaryl sulphonates.

Among the quaternary ammonium salts of formula (XVII), preference is given on the one hand to tetraalkylammonium salts, for example dialkyldimethylammonium or alkyltrimethylammonium salts in which the alkyl group comprises approximately 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyldimethylstearylammonium salts, or, on the other hand, palmitylamidopropyltrimethylammonium salt, stearamidopropyltrimethylammonium salt, stearamidopropyldimethylketearylammonium salts, or stearamidopropyldimethyl salts (myristyl acetate)ammonium sold as the name Ceraphyl® 70 by the company Van Dyk. It is in particular preferable to use the chloride salts of these compounds;

- the quaternary ammonium salts of imidazoline, for example those of formula (XVIII) below:

(XVIII)

in which :

- R ₃₂ represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example derivatives of tallow fatty acids,

- R ₃₃ represents a hydrogen atom, a C ₁ to C ₄ alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms,

- R ₃₄ represents a C ₁ to C ₄ alkyl group,

- R ₃₅ represents a hydrogen atom or a C ₁ to C ₄ alkyl group,

- X ^- is an anion chosen from the group of halides, phosphates, acetates, lactates, alkyl sulphates and alkyl- or alkylarylsulphonates, the alkyl and aryl groups of which preferably comprise, respectively, from 1 to 20 carbon atoms and from 6 to 30 carbon atoms.

Preferably, R ₃₂ and R ₃₃ denote a mixture of alkenyl or alkyl groups comprising from 12 to 21 carbon atoms, for example derivatives of tallow fatty acids, R ₃₄ denotes a methyl group and R ₃₅ denotes an atom of hydrogen. Such a product is marketed, for example, under the name Rewoquat® W 75 by the company Rewo;

- di- or tri-quaternary ammonium salts, in particular of formula (XIX):

(XX)

in which :

- R ₃₆ denotes an alkyl group comprising approximately 16 to 30 carbon atoms, optionally hydroxylated and/or interrupted by one or more oxygen atoms;

- R ₃₇ is chosen from hydrogen, an alkyl radical comprising from 1 to 4 carbon atoms or a group (R _36a )(R _37a )(R _38a )N-(CH ₂ ) ₃ ,

- R _36a , R _37a , R _38a , R ₃₈ , R ₃₉ , R ₄₀ and R ₄₁ , which may be identical or different, are chosen from hydrogen and an alkyl radical comprising from 1 to 4 carbon atoms, and

- X ^- is an anion chosen from the group of halides, acetates, phosphates, nitrates and methyl sulphates.

Such compounds are, for example, Finquat CT-P, sold by the company Finetex (Quaternium 89), and Finquat CT, sold by the company Finetex (Quaternium 75);

- quaternary ammonium salts comprising at least one ester function, such as those of formula (XX) below:

(XX)

in which :

- R ₄₂ is chosen from C ₁ to C ₆ alkyl groups and C ₁ to C ₆ hydroxyalkyl or dihydroxyalkyl groups;

- R ₄₃ is chosen from:

the group

- R ₄₇ groups, which are C ₁ to C ₂₂ hydrocarbon groups, linear or branched, saturated or unsaturated,

- a hydrogen atom;

- R ₄₅ is chosen from:

- the group

- R ₄₉ groups, which are groups based on C ₁ to C ₆ hydrocarbons, linear or branched, saturated or unsaturated,

- a hydrogen atom;

- R ₄₄ , R ₄₆ and R ₄₈ , which may be identical or different, are chosen from C ₇ to C ₂₁ hydrocarbon groups, linear or branched, saturated or unsaturated;

- r, s and t, which may be identical or different, are integers ranging from 2 to 6;

- y is an integer between 1 and 10;

- x and z, which may be identical or different, are integers ranging from 0 to 10;

- X ^- is a simple or complex and organic or inorganic anion;

provided that the sum x + y + z is between 1 and 15, that when x is 0 then R ₄₃ denotes R ₄₇ , and that when z is 0 then R ₄₅ denotes R ₄₉ .

The R ₄₂ alkyl groups can be linear or branched, and more particularly linear.

More preferably, R ₄₂ denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.

Advantageously, the sum x + y + z is between 1 and 10.

When R ₄₃ is a hydrocarbon group R ₄₇ , it can be long and contain 12 to 22 carbon atoms, or can be short and contain 1 to 3 carbon atoms.

When R ₄₅ is a hydrocarbon group R ₄₉ , it preferably contains 1 to 3 carbon atoms.

Advantageously, R ₄₄ , R ₄₆ and R ₄₈ , which may be identical or different, are chosen from C ₁₁ to C ₂₁ hydrocarbon groups, linear or branched, saturated or unsaturated, and more particularly from C 11 to C 21 alkyl and alkenyl groups. ₁₁ to C ₂₁ , linear or branched, saturated or unsaturated.

Preferably, x and z, which may be the same or different, are equal to 0 or 1.

Advantageously, y is equal to 1.

Preferably, r, s and t, which may be identical or different, are equal to 2 or 3, and more particularly still are equal to 2.

The anion X ⁻ is preferably a halide (chloride, bromide or iodide) or an alkyl sulphate, more particularly methyl sulphate. However, it is possible to use methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate or lactate, or any other anion compatible with ammonium carrying an ester function.

The anion X ⁻ is even more particularly chloride or methyl sulfate.

The ammonium salts of formula (XX) in which:

R ₄₂ denotes a methyl or ethyl group;

x and y are equal to 1;

z is equal to 0 or 1;

r, s and t are equal to 2;

R ₄₃ is chosen from:

- the group

- methyl, ethyl or C ₁₄ to C ₂₂ hydrocarbon groups,

- a hydrogen atom;

R ₄₅ is chosen from:

- the group

- a hydrogen atom;

R ₄₄ , R ₄₆ and R ₄₈ , which may be identical or different, are chosen from C ₁₃ to C ₁₇ hydrocarbon groups, saturated or unsaturated, linear or branched, and preferably from C 13 to C ₁₃ alkyl and alkenyl groups. C ₁₇ , saturated or unsaturated, linear or branched.

Advantageously, the hydrocarbon groups are linear.

By way of examples, the compounds of formula (XX) may be included, such as diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethylmethylammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyloxyethylmethylammonium and monoacyloxyethylhydroxyethyldimethylammonium (chloride or methylsulfate in particular), and mixtures thereof. The acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be the same or different.

These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine, optionally oxyalkylenated, with C ₁₀ to C ₃₀ fatty acids or with mixtures of C ₁₀ to C ₃₀ fatty acids of origin vegetable or animal, or by transesterification of their methyl esters. This esterification is followed by quaternization using an alkylating agent such as an alkyl halide (preferably a methyl or ethyl halide), a dialkyl sulphate (preferably a methyl sulphate or ethyl), methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.

Such compounds are sold, for example, under the names Dehyquart® by the company Henkel, Stepanquat® by the company Stepan, Noxamium® by the company CECA or Rewoquat® WE 18 by the company Rewo-Witco.

Among these compounds, mention may in particular be made of dipalmitoylethylhydroxyethylmethylammonium methosulphate.

The composition according to the present invention may contain, for example, a mixture of monoester, diester and triester quaternary ammonium salts with a majority by weight of diester salts.

It is also possible to use ammonium salts containing at least one ester function which are described in patents US-A-4,874,554 and US-A-4,137,180.

The behenoylhydroxypropyltrimethylammonium chloride sold by KAO under the name Quatarmin BTC 131 can be used.

Preferably, the ammonium salts containing at least one ester function contain two ester functions.

Among the quaternary ammonium salts containing at least one ester function, which can be used, it is preferred to use the dipalmitoyl-ethyl-hydroxy-ethyl-methyl-ammonium salts.

The cationic surfactants which may be present in the cosmetic composition of the invention are preferably chosen from those of formula (XVII) and mixtures thereof, and more preferably from behenyltrimethylammonium chloride and cetrimonium chloride.

The total amount of the cationic surfactant(s), when they are present in the composition according to the invention, preferably ranges from 0.5 to 15% by weight, and more preferably from 1 to 10% by weight, relative to the weight composition total.

The weight ratio (Rb) between the total quantity of fatty acid triglycerides (ii) containing from 6 to 16 carbon atoms and the total quantity of cationic surfactant(s), when they are present in the composition according to invention, is preferably greater than or equal to 1, more preferably this weight ratio ranges from 1 to 10, and better still from 1 to 5.

Organic solvents

The composition according to the present invention may also comprise one or more organic solvent(s).

Preferably, the organic solvent(s) are chosen from linear or branched monoalcohols having from 1 to 8 carbon atoms and more preferably from 1 to 4 carbon atoms, polyols, polyethylene glycols, aromatic alcohols and mixtures thereof.

Mention may in particular be made, as examples of organic solvents which can be used according to the invention, of ethanol, propanol, butanol, isopropanol, isobutanol, propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol, pentylene glycol, hexylene glycol, glycerol, sorbitol, benzyl alcohol, phenoxyethanol and mixtures thereof.

The total amount of organic solvent(s), when they are present in the composition according to the invention, is preferably between 0.005 and 1% by weight, relative to the total weight of the composition.

Water

The composition according to the present invention may additionally comprise water.

The total amount of water which may be present in the composition according to the present invention is preferably between 50 and 99% by weight, more preferably between 55 and 95% by weight, and better still between 60 and 80% by weight. weight, relative to the total weight of the composition.

Additives

The composition according to the present invention may also comprise one or more additive(s) other than the compounds of the invention.

As additives which can be used according to the invention, mention may be made of anionic, nonionic or amphoteric surfactants, cationic, amphoteric, anionic or nonionic polymers, antidandruff agents, anti-seborrheic agents, agents for preventing hair loss hair and/or to promote hair regrowth, vitamins and provitamins including tocopherol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, mineral or organic thickeners, in particular polymeric, opacifiers or pearlescent agents, antioxidants, hydroxy acids, fragrances and preservatives.

It goes without saying that those skilled in the art will take care to select this or these optional additional compounds in such a way that the advantageous properties intrinsically associated with the composition according to the invention are not, or are not substantially, negatively affected by the planned additions.

The aforementioned additives can generally be present in an amount, for each of them, of between 0.001% and 20% by weight, relative to the total weight of the composition.

The pH of the composition according to the invention is between 7.5 and 10, preferably between 8 and 9.5, more preferably between 8.5 and 9.

The pH of the composition can be adjusted to the desired value by means of commonly used alkalizing agents or acidifying agents. Examples of alkalizing agents are ammonia, alkanolamines, mineral or organic hydroxides. The acidifying agents are for example mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid and sulfonic acids.

According to a preferred embodiment, the composition of the present invention further comprises one or more alkaline agents.

Among the alkaline agents which can be used in the present invention, mention may be made of aqueous ammonia, alkali metal, alkaline-earth or guanidine (bi)carbonates, alkanolamines, such as mono-, di- and triethanolamines as well as as their derivatives, alkali or alkaline-earth metal silicates, alkali or alkaline-earth metal hydroxides, such as sodium or potassium hydroxide, and the compounds of the following formula (XXI):

(XXI)

formula (XXI) in which W is a linear or branched (C ₁ -C ₆ ) alkylene group, in particular propylene, optionally substituted by one or more hydroxyl groups; R ₆ , R ₇ , R ₈ and R ₉ , which may be identical or different, represent a hydrogen atom or a C ₁ -C ₄ alkyl radical or a C ₁ -C ₄ hydroxyalkyl radical.

The organic alkaline agent(s) are preferably chosen from organic amines having a pKb at 25° C. of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that this is the pKb corresponding to the function with the greatest basicity. In addition, organic amines do not contain an alkyl or alkenyl fatty chain comprising more than ten carbon atoms.

Preferably, the alkaline agent(s) are chosen from aqueous ammonia, alkanolamines such as monoethanolamine or ethanolamine, carbonates, in particular guanidine carbonate, silicates, in particular sodium silicate, and mixtures thereof.

Another object of the present invention relates to a cosmetic process for styling and/or conditioning keratinous fibers, in particular human keratinous fibers such as the hair, which consists in applying to said keratinous fibers a composition as defined above, and after an optional exposure time, optionally to be removed by rinsing.

The composition can be used as a leave-in product.

After an optional exposure time, the composition can preferably be removed by rinsing with water. The fibers can then be dried or left to dry.

In general, the exposure time of the composition on the keratinous fibers can range from a few seconds to 12 hours, preferably from 5 seconds to 60 minutes and even better from 10 seconds to 15 minutes, or even better from 10 seconds to 5 minutes .

The composition can be applied to wet or dry keratinous fibres, preferably to wet keratinous fibres.

The composition according to the invention is generally applied to dry keratinous materials which have optionally been washed with a shampoo.

In the present invention, the term “keratinous fibers” denotes human keratinous fibers, and in particular human hair.

The following example serves to illustrate the invention without however being limiting.

EXAMPLES

In the example which follows and unless otherwise indicated, the quantities are given in mass percentages of active ingredient (ai) relative to the total weight of the composition.

I. Risk of breakage during combing

To. Compositions

The following compositions A1 (invention) and B1 and B2 (comparative) were prepared from the ingredients indicated in Table 1 below (% by weight of active ingredient (AM)):

A1 (invention) B1 (comparative) B2 (comparative) Cocos nucifera (coconut) oil 5 - 5 Cysteine 0.75 0.75 - Cetearyl alcohol 5 5 5 Sononyl isononanoate 2.5 2.5 2.5 Behentrimonium chloride 3.95am 3.95am 3.95am Cetyl esters (and) cetyl esters 2.5 2.5 2.5 Prunus armeniana (apricot) seed powder 0.25 0.25 0.25 Bis-cetearyl amodimethicone 0.4 0.4 0.4 Ethanolamine 0.53 0.53 0.53 Hydroxyethylcellulose 0.4 0.4 0.4 Tocopherol 0.1 0.1 0.1 Scent 1 1 1 pH agent Qs pH 8.8 Qs pH 8.8 Qs pH 8.8 Water Qs 100 Qs 100 Qs 100

Formula pH = 8.8

b. Protocol

In this mechanical evaluation process, hair fibers are subjected to repeated low amplitude extension cycles until the fiber breaks or the maximum number of cycles set by the operator is reached. At the end of the fatigue test, the life of the fiber is measured. It corresponds to the number of extension cycles that the fiber has endured without breaking.

The mechanical tensile stress that is applied to the fiber can be constant strain, constant force, or constant stress. For this analysis, cyclic fatigue tests were carried out at a constant stress of 144MPa, using a Diastron CYC 801 cyclic fatigue testing machine. Cross-sectional area measurements are carried out using of a fiber dimensional analysis system (FDAS, Diastron) and are used to obtain a correct target stress.

The following protocol was used for each composition A1, B1 and B2 on multi-ethnic virgin hair (4-5 curl pattern) from IHIP:

1. Prepare a 1 g lock of hair.

2. Wash 1 g of hair with 0.4 g of Au Naturale shampoo (commercial product).

3. Dry the wick with a towel

4. Apply 4g of each composition A1, B1 and B2 to 1g of damp lock of hair.

5. Leave the treated hair on a hot plate at 31 degrees Celsius (for 15 minutes).

6. Rinse off the treatment after 15 minutes

7. Dry the hair by blowing cold air, and

8. Comb the hair (120 comb strokes)

Steps 2-8 of the above protocol were repeated 5 times (5 treatments and 600 comb strokes).

The following protocol was used as a control on multi-ethnic virgin hair (4-5 curl pattern) from IHIP:

1. Prepare a 1 g lock of hair.

2. Wash 1g of hair with 0.4g of Au Naturale shampoo.

3. Dry the wick with a towel

4. Dry the hair by blowing cold air, and

5. Comb the hair (120 comb strokes).

Steps 2-5 of the control protocol above were repeated 5 times (5 treatments and 600 comb strokes).

vs. Results

The results thus obtained for each composition A1, B1 and B2 are expressed in Table 2 below. The higher the number of cycles before breaking, the more resistant the hair.

A1 (invention) B1 (comparative) B2 (comparative) Witness Average cycle before rupture 6560 5154 4249 4333

The results thus obtained show that the claimed composition A1, which comprises the combination of cysteine with a particular fatty acid triglyceride, makes it possible to strengthen curly hair by increasing the average number of cycles before breaking. Indeed, the number of cycles before breaking is significantly higher when the hair is treated with the claimed composition A1 compared to the comparative compositions B1 and B2 comprising either cysteine or the particular fatty acid triglyceride only.

Thus, the combination of cysteine with at least one fatty acid triglyceride containing 6 to 16 carbon atoms provides a synergistic effect in strengthening curly hair.

II. Ease of combing

To. Compositions

Compositions A1 (invention) and B1 and B2 (comparison) were prepared from the ingredients indicated in Table 1 of Example I.

b. Protocol

The combing process measures the combing force of a lock on a Lloyd extensiometer (Ametek Inc, USA). The weaker the force, the easier it is to comb the hair.

A wide-toothed comb attachment, resembling a comb typically used for natural African hair was used. The afro comb had teeth spaced ~3mm apart and was attached to the instrument gantry as shown below. To carry out the test, a sample (~1g) is inserted in the center of the comb and the wick is tightened on the sensor. The sample is moved by the gantry in a linear translation and the comb forces are measured. This movement is repeated 4 times and the average combing force is used to estimate the effectiveness of the tested composition. The weaker the force, the easier it is to comb the hair.

The following protocol was used for each composition A1, B1 and B2 on 7-8 curl model hair from South Africa:

1. Each 1g strand of afro hair was washed with 0.4g Au Naturale shampoo (commercial product) then rinsed.

2. 1g of each composition A1, B1 and B2 was applied to each gram of damp hair from step 1.

3. Leave the treated hair on a hot plate at 31 degrees Celsius (for 15 minutes).

4. The wick was then rinsed and left to dry for 24 hours at room temperature (±22°C).

Steps 1-4 of the above protocol were repeated 5 times.

A similar protocol including only steps 1, 3 and 4 of the above protocol was used as a control.

At the end of the process, the locks of hair were left to dry in the open air for 24 hours and then characterized for the combing force using a Lloyd tensiometer.

vs. Results

The results thus obtained for each composition A1, B1 and B2 are expressed in Table 3 below.

A1 (invention) B1 (comparative) B2 (comparative) Witness Total work required to comb the hair (average in Joules) 1472 2246 1917 2283

The results thus obtained show that the claimed composition A1, which comprises the combination of cysteine with a particular fatty acid triglyceride, improves the styling of very curly hair. Indeed, combing is significantly easier when the hair is treated with the claimed composition A1 compared to comparative compositions B1 and B2 comprising either cysteine or the particular fatty acid triglyceride only.

Thus, the combination of cysteine with at least one fatty acid triglyceride containing 6 to 16 carbon atoms ensures a synergistic effect on the ease of combing very curly hair.

III. Compositions according to the present invention

The following compositions A2, A3 and A4 according to the present invention were prepared from the ingredients indicated in Table 4 below (% by weight of active ingredient (AM)):

A2 A3 A4 Cocos nucifera (coconut) oil 5 5 5 Cysteine 0.75 0.65 0.65 Cetearyl alcohol 4.5 4.5 4.5 Isononyl isononanoate 2.5 2.5 2.5 Behentrimonium chloride 3.95 3.95 3.95 Cetyl esters 2 - 2 Prunus armeniana (apricot) seed powder 0.25 0.25 0.25 Bis-cetearyl amodimehicone 0.4 0.4 0.4 Ethanolamine (Qs) Qs pH 9 Qs pH 9 Qs pH 9 Hydroxyethylcellulose 0.4 - 0.4 Tocopherol 0.1 0.1 0.1 PEG-180 2 2 2 Isopropylic alcohol - 0.9 0.9 Dye - 0.0225 - Scent 1 1 0.9 Water Qs 100 Qs 100 Qs 100

The hair treated with compositions A2, A3 and A4 thus obtained is not only easy to detangle and quick to comb, but its manageability to styling is also very good. In addition, compositions A2-A3 give the hair good conditioning properties, especially in terms of softness and volume. The hair is also strengthened.

Claims (10)

Composition comprising:
(i) cysteine and/or one of its derivatives such as N-acetylcysteine, an N-alkanoylcysteine and the alkyl esters of cysteine,
(ii) one or more fatty acid triglycerides containing from 6 to 16 carbon atoms in a total amount greater than or equal to 1% by weight, relative to the total weight of the cosmetic composition;
the pH of said composition ranging from 7.5 to 10, and
said composition being free of additional reducing agent other than cysteine or its derivatives (i). Composition according to Claim 1, in which the total quantity of cysteine and/or of one of its derivatives (i) is less than or equal to 1% by weight, preferably between 0.05 and 1% by weight, more preferably between 0.1 and 1% by weight, and better still between 0.5 and 0.8% by weight, relative to the total weight of the composition. Composition according to any one of the preceding claims, in which the fatty acid triglyceride(s) (ii) contain from 6 to 14 carbon atoms, preferably from 6 to 12 carbon atoms. Composition according to any one of the preceding claims, in which the fatty acid triglyceride(s) (ii) are chosen from coconut oil, caprylic/capric acid triglycerides, palm kernel oil, of babasu, cuphea oil and mixtures thereof. Composition according to any one of the preceding claims, in which the total quantity of fatty acid triglyceride(s) containing from 6 to 16 carbon atoms (ii) is between 1 and 15% by weight, and preferably between 2 and 10% by weight, relative to the total weight of the composition. Composition according to any one of the preceding claims, in which the weight ratio between the total quantity of triglyceride(s) of fatty acid(s) containing from 6 to 16 carbon atoms (ii) and the total quantity of cysteine and/ or one of its derivatives (i) is greater than or equal to 1, preferably ranges from 1 to 20, and more preferably from 2 to 15. Composition according to any one of the preceding claims, characterized in that it also comprises one or more additional fatty substances different from the triglyceride(s) of fatty acids containing from 6 to 16 carbon atoms (ii), preferably chosen from C ₆ to C ₁₆ hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils of animal origin, triglycerides other than fatty acid triglycerides (ii) previously described, fluoro oils, fatty alcohols not polyoxyalkylenated, esters of fatty acids and/or fatty alcohols other than triglycerides, vegetable waxes, non-silicone waxes, silicones and mixtures thereof, and more preferentially among fatty alcohols, fatty esters, vegetable oils of the triglyceride type other than fatty acid triglycerides (ii), aminosilicones and mixtures thereof. Composition according to any one of the preceding claims, in which the total quantity of fatty substances is between 1 and 35% by weight, and preferably between 5 and 25% by weight, relative to the total weight of the composition. Composition according to any one of the preceding claims, in which it additionally comprises one or more cationic surfactant(s), preferably chosen from the following quaternary ammonium salts, and mixtures thereof:
- quaternary ammonium salts corresponding to the general formula (XVII) below:
(XVII)
in which the groups R ₂₈ to R ₃₁ , which may be identical or different, represent an aliphatic group, linear or branched, containing from 1 to 30 carbon atoms, or an aromatic group, at least one of the groups R ₂₈ to R ₃₁ denoting a group comprising from 8 to 30 carbon atoms; the aliphatic groups can comprise heteroatoms such as in particular oxygen, nitrogen, sulfur and halogens;
- quaternary ammonium salts of imidazoline;
- di- or tri-quaternary ammonium salts;
- quaternary ammonium salts containing at least one ester function;
and more preferably chosen from behenyltrimethylammonium chloride and cetrimonium chloride. Cosmetic process for combing and/or styling keratinous fibres, in particular human keratinous fibers such as the hair, which consists in applying to said keratinous fibers a composition as defined in any one of the preceding claims, and after a optional laying, optionally to be removed by rinsing.