WO2006010647A2

WO2006010647A2 - Cosmetic composition comprising at least one surfactant having at least one point of molecular fragility, process therefor and uses thereof

Info

Publication number: WO2006010647A2
Application number: PCT/EP2005/009890
Authority: WO
Inventors: Géraldine Fack; Henri Samain
Original assignee: L'oreal
Priority date: 2004-07-29
Filing date: 2005-07-29
Publication date: 2006-02-02
Also published as: WO2006010647A3

Abstract

The present invention relates to cosmetic compositions intended simultaneously for cleansing and/or conditioning fibres, more particularly human keratin fibres such as the hair, and comprising, in a cosmetically acceptable support, at least one cationic surfactant having at least one point of molecular fragility and at least one cosmetic agent. The invention also relates to the uses of the said compositions in the abovementioned cosmetic applications and to a process using the said compositions.

Description

COSMETIC COMPOSITION COMPRISING AT LEAST ONE SURFACTANT HAVING AT LEAST ONE POINT OF MOLECULAR FRAGILITY, PROCESS THEREFOR AND USES THEREOF

The present invention relates to cosmetic compositions especially for cleansing and/or conditioning fibres, more particularly human keratin fibres such as the hair, comprising at least one surfactant having at least one point of molecular fragility. The invention also relates to the uses of the said cosmetic compositions for cleansing and/or conditioning fibres and to a process using the said compositions.

Surfactants are agents that are very commonly used in cosmetics, more particularly in cosmetic compositions for hair hygiene and hair care.

It is common practice to use compositions such as shampoos essentially comprising a mixture of standard surfactants especially of anionic type, for cleansing and/or washing the hair. These compositions are applied to wet hair and the lather generated by massaging or friction with the hands makes it possible, after rinsing with water, to remove the diverse soiling matter initially present on the hair.

It is known practice to use compositions such as hair conditioners essentially comprising a mixture of standard surfactants especially of cationic type, for conditioning and treating the hair. These compositions are applied to washed and moistened hair, and the massaging or friction of the said composition with the hands on the hair results, after rinsing with water, in conditioning of the hair.

However, when it is a matter of an application of shampoo or hair conditioner type, once these surfactants have fulfilled their detergent and/or conditioning functions, they are largely removed from the hair during the rinsing step. A large number of molecules with intrinsic surfactant properties, with all the implications following therefrom for the environment in terms of biodegradability and ecotoxicity, thus pass into the wastewater circuit.

The Applicant has. thus sought to obtain cosmetic compositions, especially intended for preparing shampoos and hair conditioners, comprising surfactants that degrade satisfactorily; i.e. they satisfy the standard biodegradability tests recommended by the OCDE (easy biodegradability tests OCDE No. 301 , intrinsic biodegradability tests OCDE No. 302 and purification plant simulation tests No. 303).

The Applicant has just discovered, advantageously and unexpectedly, that the use of surfactants having at least one point of molecular fragility makes it possible to improve the biodegradability of the cosmetic compositions while at the same time maintaining good detergent and/or conditioning properties. For the purposes of the present invention, the term "point of molecular fragility" means a covalent chemical bond that breaks easily under the effect of an external stimulus. External stimuli that may especially be mentioned include pH variations, the action of temperature, visible, ultraviolet or infrared radiation, variations in salinity, the action of microwaves or sound waves or ultrasound waves, and the action of enzymes.

The compositions according to the invention are of major interest in terms of impact on the environment, since these compositions degrade easily and are therefore more biodegradable and less ecotoxic.

In addition, when these compositions are used as detergent compositions of shampoo type, they make it possible to obtain a rich lather and good detergency, and also allow good ease of removal of the soiling matter on rinsing. When they are used in applications of hair conditioner type, these compositions also make it possible to limit the harmful or adverse effects induced by the various treatments or attacking factors to which hair fibres are more or less repeatedly subjected. In general, these compositions also give washed, dry or moistened hair ease of disentangling, softness and smoothness that are at least comparable with and often better than those that may be obtained with standard cleansing compositions not comprising such a surfactant having a point of molecular fragility.

One subject of the invention is thus a cosmetic composition, especially for cleansing and/or conditioning fibres, more particularly human keratin fibres such as the hair, comprising, in a cosmetically acceptable support, at least one cationic surfactant having at least one point of molecular fragility and at least one cosmetic agent.

Another subject of the invention is the use of the said cosmetic compositions for cleansing and/or conditioning fibres, comprising at least one cationic surfactant having at least one point of molecular fragility and at least one cosmetic agent.

A subject of the invention is also a process for washing and/or conditioning keratin materials such as the hair, which consists in applying to the said moistened fibres an effective amount of a composition comprising at least, one cationic sufactant having at least one point of molecular fragility and at least one cosmetic agent, as defined above, and then, after an optional leave in time, in rinsing with water.

Other characteristics, aspects, subjects and advantages of the present invention will emerge even more clearly on reading the description and the examples that follow. 90

4

According to the invention, the cosmetic compositions comprise, in a cosmetically acceptable medium, at least one cationic surfactant having at least one point of molecular fragility and at least one cosmetic agent. In the context of the present invention, the term "cationic surfactant having at least one point of molecular fragility" means a cationic surfactant that is present in an amount of 20 mM in aqueous medium having a degree of degradation of at least 90% after 72 hours at 27°C in the presence of 2% HCl, i.e. not more than 10% of starting surfactants remains.

The cationic surfactants that may be used in the present invention may comprise a dioxolane group, 1-O-alkylglycerol group, siloxane group and/or β-aryloxysulfone group.

In the context of the present invention, and unless otherwise indicated, the term "alkyl" means linear or branched, cyclic or acyclic hydrocarbon-based radicals containing from 1 to 100 carbon atoms and preferably from 1 to 50 carbon atoms, for example methyl, ethyl, n-propyl, etc. An alkoxy radical is a radical alk-O, the alkyl radical having the definition given above.

In the context of the present invention, the term "aryl" means a benzene nucleus substituted with an alkyl group.

The cationic surfactants comprising a dioxolane group are compounds comprising the following ring system:

' O-CH —

As cationic surfactants comprising a dioxolane group that may be used in the present invention, examples that may be mentioned include the compounds of formulae (1) to (5) below:

R_3N 0-CH-R₁

C X O—CH-R₂ (3)

R'-N— R" R"

in which R₁, R₂ and R₃ represent, independently of each other, a hydrogen atom, a hydroxyl group, an optionally substituted amino group, a hydrocarbon-based chain containing from 1 to 100 carbon atoms, which is preferably linear or branched, cyclic or non-cyclic, saturated or unsaturated, optionally interrupted with one or more hetero atoms or carbonyl groups and optionally substituted with one or more groups chosen from hydroxyl, halo and amido groups, R' , R" , R" ' , R'₂, R"₂ and R' " ₂ represent, independently of each other, a C₁-C₆ and preferably C₁-C₄ alkyl or hydroxyalkyl radical, and

X and X' represent, independently of each other, a divalent group and preferably a linear or branched C₁-C₃₀ alkylene group, with at least one from among R₁, R₂ and R₃ representing a hydrocarbon-based chain containing a number of carbon atoms of greater than or equal to 8.

Among the cationic surfactants comprising a dioxolane group that are preferably used are the compounds of formulae (1 ) and (2).

The cationic surfactant(s) comprising a. 1 -O-alkylglycerol group that may be used in the present invention is (are) compounds comprising the following ring system:

The cationic surfactant(s) comprising a 1 -O-alkylglycerol group that may be used in the present invention is (are) compounds having the following formula:

in which R₁, R' , R" , R' " , R'₂, R"₂, R" ⁵2, X and X' have the same meanings as above.

The cationic surfactant(s) comprising a siloxane group that may be used in the present invention is (are) compounds comprising the following ring system:

CH₃ ^R ₄

CH₃-C Si — O—

CH₃ R₅

in which R₄ and R₅ represent, independently of each other, a hydrogen atom or a C₁-C₃₀ alkyl radical, with at least one from among R₄ and R₅ representing an alkyl containing a number of carbon atoms of greater than or equal to 8.

In particular, the cationic surfactant(s) comprising a siloxane group that may be used in the present invention is (are) compounds having the following formula:

in which R₄ and R₅ represent, independently of each other, a hydrogen atom or a C₁-C₃₀ alkyl group, X, R' , R" and R' " having the same meaning as above, with at least one from among R₄ and R₅ representing a hydrocarbon-based chain containing a number of carbon atoms of greater than or equal to 8.

The cationic surfactant(s) comprising a β-aryloxy sulfone group that may be used in the present invention is (are) compounds comprising the following ring system:

In particular the cationic surfactant(s) comprising a β-aryloxy sulfone group that may be used in the present invention is (are) compounds having the following formula:

in which X, R' , R" and R' " have the same meaning as above and R₆ represents a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon-based chain containing from 8 to 100 carbon atoms and preferably from 8 to 50 carbon atoms, optionally interrupted with one or more hetero atoms or carbonyl groups and optionally substituted with one or more groups chosen from hydroxyl, halo and amido groups.

The abovementioned cationic surfactants may be used alone or as a mixture and may be obtained from synthetic processes described in the literature, for example in the following articles: S. Yamamura, M. Nakamura and T. Takeda, J. Am. Oil. Chem. Soc , Vol. 66, 1989, 1165-1169; S. Yamamura, K. Shimaki, T. Nakajima, T. Takeda, I. Ikeda and M. Okahara, J. Jpn. Oil. Chem. Soc , Vol. 40, 1991 , 16-19; D. Ono, S. Yamamura, M. Nakamura and T. Takeda, J. Jpn. Oil. Chem. Soc , Vol. 49, 2000, 785-791.

Generally, the concentration of the cationic surfactant(s) having a point of molecular fragility used in the composition is between 0.01% and 40% by weight relative to the total weight of the said composition, preferably between 0.1% and 25% and even more preferably between 0.5% and 18% by weight relative to the weight of this composition.

The cosmetic agent(s) contained in the composition according to the invention is (are) chosen from reducing agents, oxidizing agents, moisturizers, emollients, sunscreens, direct dyes or oxidation dyes precursors, pigments, mineral fillers, clays, hydroxy acids, colloidal minerals, fragrances, fixing or non-fixing polymers, vitamins or provitamins, thickeners, antidandruff agents, sequestering agents, antifoams, mineral or organic acids and bases, plasticizers, peptizers, preserving agents, conditioning agents, and additional surfactants other than the surfactants having a point of molecular fragility.

The concentration of cosmetic agent is generally between 0.001% and 20% and preferably between 0.01% and 10% by weight relative to the total weight of the composition according to the invention.

The compositions according to the invention have a final pH generally of between 2 and 10 and preferably between 3 and 8. The adjustment of the pH to the desired value may be performed conventionally by adding a base (organic or mineral base) to the composition, for example aqueous ammonia or a primary, secondary or tertiary (poly)amine, for example monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1 ,3-propanediamine, or alternatively by addition of an acid, preferably a carboxylic acid, for instance citric acid.

The compositions in accordance with the invention may contain, in addition to the combination defined above, viscosity regulators such as electrolytes. Mention may be made in particular of sodium chloride, sodium xylenesulfonate, scleroglucans, xanthan gums, fatty acid alkanolamides, alkyl ether carboxylic acid alkanolamides optionally oxyethylenated with up to 5 mol of ethylene oxide, such as the product sold under the name "Aminol Al 5" by the company Chem Y, crosslinked polyacrylic acids and crosslinked acrylic acid/ C₁₀-C₃₀ alkyl acrylate copolymers. These viscosity regulators are used in the compositions according to the invention in proportions that may be up to 10% by weight relative to the total weight of the composition.

The compositions in accordance with the invention may also contain up to 5% of nacreous agents or opacifiers that are well known in the prior art, for instance sodium or magnesium palmitates, sodium or magnesium stearates and hydroxystearates, fatty-chain acyl derivatives such as ethylene glycol or polyethylene glycol monostearates or distearates, fatty-chain ethers such as distearyl ether or 1-hexadecyloxyoctododecanol, and nacres.

The compositions in accordance with the invention may also optionally contain other agents that have the effect of improving the cosmetic properties of keratin materials. Mention may be made of anionic, nonionic, cationic or amphoteric polymers, proteins, protein hydrolysates, ceramides, pseudoceramides, fatty acids containing linear or branched C₁₆-C₄₀ chains, such as 18-methyleicosanoic acid, modified or unmodified, volatile or non-volatile silicones, mineral, organic or plant oils, oxyethylenated or non-oxyethylenated waxes, paraffins, fatty acids, fatty amides, fatty esters and fatty alcohols, and mixtures thereof.

Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s) such that the advantageous properties intrinsically associated with the oxidation dye composition in accordance with the invention are not, or are not substantially, adversely affected by the envisaged addition(s).

The appropriate cosmetically acceptable medium generally consists of water or of a mixture of water and of at least one organic solvent to dissolve the compounds that are not sufficiently water- soluble. Examples of organic solvents that may be mentioned include branched or unbranched C₁-C₄ lower alcohols, such as ethanol and isopropanol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, glycerol and aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.

The solvents may be present in proportions preferably of between 0.1 % and 40% by weight approximately, and even more preferably between 1 % and 30% by weight approximately, relative to the total weight of the dye composition.

These compositions may be in the form of more or less thickened liquids, creams or gels, and they are mainly suitable for washing, conditioning and caring for keratin materials such as the skin or the hair.

The formulations may be in various galenical forms such as a lotion, a spray, an aerosol foam, a pump foam, a shower gel, a hair conditioner or a shampoo, for example.

The compositions according to the invention are preferably used as shampoos or hair conditioners for washing and/or conditioning the hair, and, in this case, they are applied to wet hair in amounts that are effective to wash and/or condition it, this application being followed by rinsing with water.

The compositions in accordance with the invention may also be used as shower gels for washing and conditioning the skin, in which case they are applied to the skin and are rinsed off after application.

A subject of the invention is also the cosmetic use of the above compositions for cleansing or conditioning keratin materials such as the hair and the skin.

The compositions may be ^' used, for example, for removing makeup from keratin materials such as the skin, for example from the face, the neck or the lips, the eyelashes or the eyebrows.

A subject of the invention is also a process for washing and conditioning keratin materials such as the hair, which consists in applying to the said moistened materials an effective amount of a composition as defined above, followed by rinsing with water after an optional leave-in time.

The examples that follow serve to illustrate the invention without, however, being limiting in nature.

EXAMPLES

Example 1

Compound (I) below is prepared:

The synthesis of this compound comprising a dioxolane group is described in the following articles: S. Yamamura, M. Nakamura and T. Takeda, J. Am. Oil. Chem. Soc , Vol. 66, 1989, 1 165- 1 169; S . Yamamura, K. Shimaki, T. Nakaj ima, T. Takeda, I. Ikeda and M. Okahara, J Jpn. Oil. Chem. Soc , Vol. 40, 1991 , 16- 19.

Example 2

The following composition is prepared, the amounts indicated being weight percentages relative to the total weight of the composition:

The composition is applied to a lock of sensitized hair and is then rinsed off with water.

A smoothing and disentangling effect on the fibre is observed, by sensory evaluation, which is comparable to that of the cationic surfactants of the prior art used in cosmetics. In addition, the degradation of the compound in acidic medium is very markedly improved.

Example 3

Compositions (A) to (L) according to the present invention are prepared from the following cationic surfactants:

The amounts indicated in the following tables are weight percentages relative to the total weight of the composition:

Table 1 :

Table 2

The compositions (A) to (L) are applied to a lock of sensitized hair and are then rinsed off with water.

The compositions according to the present invention confer good cosmetic properties to the hair. In particular, a smoothing and disentangling effect on the fibre is observed.

Claims

1. Cosmetic composition comprising, in a cosmetically acceptable medium, at least one cationic surfactant having at least one point of molecular fragility and at least one cosmetic agent.

2. Cosmetic composition according to Claim 1 , in which the cationic surfactant having at least one point of molecular fragility is a cationic surfactant comprising a dioxolane group:

3. Cosmetic composition according to Claim 2, in which the cationic surfactant having at least one point of molecular fragility is a cationic surfactant comprising a dioxolane group chosen from the compounds of formulae ( 1) to (5) below:

R_{3 N} 0-CH-R₁

C X O—CH-R₂ (3)

R'-N— R" R"¹

in which R₁, R₂ and R₃ represent, independently of each other, a hydrogen atom, a hydroxyl group, an optionally substituted amino group, a hydrocarbon-based chain containing from 1 to 100 carbon atoms, which is linear or branched, cyclic or non-cyclic, saturated or unsaturated, optionally interrupted with one or more hetero atoms or carbonyl groups and optionally substituted with one or more groups chosen from hydroxyl, halo and amido groups,

R' , R" , R' " , R'₂, R"₂ and R' " ₂ represent, independently of each other, a C₁-C₆ and preferably C₁-C₄ alkyl or hydroxyalkyl group, and

X and X' represent, independently of each other, a divalent group and preferably a linear or branched C₁-C₃₀ alkylene group, with at least one from among the radicals R₁, R₂ and R₃ representing a hydrocarbon-based chain containing a number of carbon atoms of greater than or equal to 8.

4. Cosmetic composition according to Claim 1 , in which the cationic surfactant having at least one point of molecular fragility comprising a 1-O-alkyglycerol group:

O I l

\ CH₂, / Q-C-CH₂-

O CH'

CH

²^O-C I l -CH

O

5. Cosmetic composition according to Claim 4, in which the cationic surfactant having at least one point of molecular fragility is a cationic surfactant comprising a 1 -0-alkylglycerol group chosen from the compounds of formula (6) below:

in which R₁ represents a hydrogen atom, a hydroxyl group, an optionally substituted amino group, a hydrocarbon-based chain containing from 1 to 100 carbon atoms, which is linear or branched, cyclic or non-cyclic, saturated or unsaturated, optionally interrupted with one or more hetero atoms or carbonyl groups and optionally substituted with one or more groups chosen from hydroxyl, halo and amido groups,

X and X' represent, independently of each other, a divalent group and preferably a linear or branched C₁-C₃₀ alkylene group, with at least one of the radicals R₁ , R₂ and R₃ representing a hydrocarbon-based chain containing a number of carbon atoms of greater than or equal to 8.

6. Cosmetic composition according to Claim I ₅ in which the cationic surfactant having at least one point of molecular fragility comprising a siloxane group:

CH₃ R₄

CH₃-C- -Si — O— CH, EU

7. Cosmetic composition according to Claim 6, in which the cationic surfactant having at least one point of molecular fragility is a cationic surfactant comprising a siloxane group chosen from the compounds of formula (7) below:

CH₃ R₄

CH₃-C Si — O— X- "Nf-R" (7)

CH₃ R₅ R"¹

in which R₄ and R₅ represent, independently of each other, a hydrogen atom or a C₁-C₃₀ alkyl group, X represents a divalent group and preferably a linear or branched C₁-C₃₀ alkylene group,

R', R" and R' " represent, independently of each other, a C₁-C₆ and preferably C₁-C₄ alkyl or hydroxyalkyl group, and with at least one from among R₄ and R₅ representing a hydrocarbon-based chain containing a number of carbon atoms of greater than or equal to 8.

8. Cosmetic composition according to Claim 1 , in which the cationic surfactant having at least one point of molecular fragility comprising a β-aryloxy sulfone group:

9. Cosmetic composition according to Claim 8, in which the cationic surfactant having at least one point of molecular fragility is a cationic surfactant comprising a β-aryloxy sulfone group chosen from the compounds of formula (8) below:

in which X represents a divalent group and preferably a linear or branched C₁-C₃₀ alkylene group,

R', R" and R' " represent, independently of each other, a C₁-C₆ and preferably C₁-C₄ alkyl or hydroxyalkyl group, and

R₆ represents a linear or branched, cyclic or acyclic, saturated or unsaturated hydrocarbon-based chain containing from 8 to 100 and preferably from 8 to 50 carbon atoms, optionally interrupted with one or more hetero atoms or carbonyl groups and optionally substituted with one or more groups chosen from hydroxyl, halo and amido groups.

10. Cosmetic composition according to one of Claims 1 to 9, in which the cationic surfactant having at least one point of molecular fragility is present in a concentration ranging from 0.01 % to 40% by weight relative to the total weight of the said composition.

11. Cosmetic composition according to Claim 10, in which the cationic surfactant having at least one point of molecular fragility is present in a concentration ranging from 0.1% to 25% by weight relative to the total weight of the said composition.

12. Composition according to any one of the preceding claims, in which the cosmetic agent(s) is (are) chosen from reducing agents, oxidizing agents, moisturizers, emollients, sunscreens, direct dyes or oxidation dyes precursors, pigments, mineral fillers, clays, hydroxy acids, colloidal minerals, fragrances, fixing or non-fixing polymers, vitamins or provitamins, thickeners, antidandruff agents, sequestering agents, antifoams, mineral or organic acids and bases, plasticizers, peptizers, preserving agents, conditioning agents, and additional surfactants other than the surfactants having a point of molecular fragility and additional surfactants other than those defined in Claims 1 to 9.

13. Composition according to Claim 12, such that the concentration of cosmetic agent(s) is between 0.001 % and 20% and preferably between 0.01% and 10% by weight relative to the total weight of the composition according to the invention.

14. Process for washing and/or conditioning keratin materials such as the hair, which consists in applying to the said moistened materials an effective amount of a composition according to one of Claims 1 to 13, followed by rinsing with water after an optional leave-in time.

15. Use of a composition according to one of Claims 1 to 13, for washing and/or conditioning keratin materials such as the hair and the skin.

16. Use of a composition according to one of Claims 1 to 13 , for the preparation of a shampoo.

17. Use of a composition according to one of Claims 1 to 13 , for the preparation of a hair conditioner.

18. Use of a composition according to one of Claims 1 to 13 , for removing makeup from keratin materials.