WO2023117783A1

WO2023117783A1 - Cosmetic composition comprising particular anionic surfactant(s), hydroxyhydrocarbyl (poly)glycoside(s) and specific carboxylic acid(s)

Info

Publication number: WO2023117783A1
Application number: PCT/EP2022/086426
Authority: WO
Inventors: Harshada TULSYAN; Shaila Bajoria
Original assignee: L'oreal
Priority date: 2021-12-21
Filing date: 2022-12-16
Publication date: 2023-06-29

Abstract

The invention relates to a cosmetic composition comprising one or more anionic surfactants of sulfosuccina(ma)te type (a), one or more hydroxyhydrocarbyl (poly)glycosides (b), and one or more compounds chosen from pyrrolidone carboxylic acid (PCA), salts thereof and derivatives thereof.

Description

DESCRIPTION

TITLE : Cosmetic composition comprising particular anionic surfactant(s), hydroxyhydrocarbyl (poly)glycoside(s) and specific carboxylic acid(s)

The present invention relates to a cosmetic composition for cleansing and conditioning keratin materials , and in particular human keratin materials such as hair and skin, which comprises one or more particular anionic surfactants, one or more hydroxyhydrocarbyl (poly)glycosides and one or more compounds chosen from pyrrolidone carboxylic acid, its salts and its derivatives.

The invention also relates to a cosmetic process for cleansing and conditioning keratin materials using this composition.

Finally, the invention relates to the use of such a composition for cleansing and conditioning keratin materials .

Anionic surfactants are generally used in compositions for cleansing keratin materials and they are known for good foaming and cleansing properties . However anionic surfactants like alkyl ether sulfates and benzyl sulfonates generally irritate skin and eyes. Hence, most of the products for babies or for sensitive skin, also called “mild compositions”, are without such surfactants . Alternative mild compositions comprise for example nonionic and/or amphoteric surfactants . Such compositions are described for example in US 2009/036339. However, they tend to suffer from poor foaming and cleansing performance.

Thus, there is a need to provide mild cleansing and care composition which can be used as rinse-off or leave-on product for effectively removing dirt, sweat, sebum and other inorganic particles from keratin materials such as hair and skin.

The Applicant has now discovered that the combination of one or more anionic surfactants of sulfosuccina(ma)te type, one or more hydroxyhydrocarbyl (poly)glycosides and one or more compounds chosen from pyrrolidone carboxylic acid, salts thereof and derivatives thereof, makes it possible to achieve the objectives outlined above.

Thus, a subject-matter of the invention is a cosmetic composition comprising:

(a) one or more anionic surfactants of sulfosuccina(ma)te type,

(b) one or more hydroxyhydrocarbyl (poly)glycosides, and

(c) one or more compounds chosen from pyrrolidone carboxylic acid (PCA), salts thereof and derivatives thereof such as those defined below.

The composition according to the invention is milder and gentler than conventional shampoos , in particular on protein denaturation. It can be used as leave-on cleanser.

This composition allows improved cleansing and conditioning of keratin materials, in particular human keratin materials such as hair and skin. In particular, it has an enhanced foaming property and a cleansing efficiency at least the same as that of shampoos containing anionic surfactants of the prior art.

The present invention also relates to a cosmetic process for cleansing and conditioning keratin materials using this composition.

Another subject-matter of the invention is the use of the composition according to the invention for cleansing and conditioning keratin materials .

In the present invention, the term “keratin materials” denotes human keratin materials, and in particular hair and skin.

The composition can be applied directly or through a spray or pump bottle. The composition can be used as shampoo or body wash or as other cleanser.

Other subject-matters, characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description and the examples that follow.

In the text herein below, unless otherwise indicated, the limits of a range of values are included in that range, for example in the expressions "between" and "ranging from ... to ..." .

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" . According to the invention, the cosmetic composition comprises :

(a) one or more anionic surfactants of sulfosuccina(ma)te type,

(b) one or more hydroxyhydrocarbyl (poly)glycosides, preferably one or more hydroxyalkyl (poly)glycosides, and

(c) one or more compounds chosen from pyrrolidone carboxylic acid, salts thereof and derivatives thereof such as those defined below .

Anionic surfactant(s) of sulfosuccina(ma)te type (a)

The anionic surfactants of sulfosuccina(ma)te type include sulfosuccinate and sulfosuccinamate anionic surfactants, that are known to be mild surfactants . They may be chosen from the following compounds : alkylsulfosuccinates , dialkylsulfosuccinates, alkyl ether sulfosuccinates, alkylamidosulfosuccinates, alkylamido ether sulfo succinates, alkyl sulfo succinamates, di alkyl sulf osuccinamates, alkyl ether sulfosuccinamates ; and salts thereof. The alkyl groups of these compounds preferably comprise from 6 to 30 carbon atoms, especially from 8 to 24, better still from 10 to 20 carbon atoms . These compounds may be polyoxyalkylenated, especially polyoxyethylenated, and then preferably comprise from 1 to 50 alkylene oxide units and better still from 2 to 10 alkylene oxide units, the alkylene oxide units being in particular ethylene oxide units .

When the anionic surfactant is in salt form, the said salt may be chosen from alkali metal salts, such as the sodium or potassium salt, ammonium salts, amine salts and in particular amino alcohol salts, and alkaline-earth metal salts, such as the magnesium salt.

Examples of amino alcohol salts that may be mentioned include monoethanolamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine or triisopropanolamine salts, 2-amino-2-methyl- 1 -propanol salts, 2-amino-2-methyl- 1 ,3- propanediol salts and tris(hydroxymethyl)aminomethane salts .

Alkali metal or alkaline-earth metal salts and in particular the sodium or magnesium salts are preferably used.

Preferentially, the anionic surfactant(s) (a) may be used in the invention alone or as a mixture of two or more anionic surfactants . Preferably, anionic surfactant(s) (a) is(are) chosen from sulfosuccinate type anionic surfactants . More preferably, it may be chosen from:

- C₈-C 24 and especially C10-C20 alkylsulfosuccinates, better lauryl sulfo succinates ;

- C₈-C 24 and especially C10-C20 dialkylsulfosuccinates ;

- C₈-C24 and especially C10-C20 alkyl ether sulfosuccinates, comprising preferably from 1 to 5 alkylene oxide groups, more preferably from 1 to 5 ethylene oxide groups, better laurethsulfosuccinates comprising from 1 to 5 ethylene oxide groups, still better from 2 to 4 ethylene oxide groups ; and

- mixtures thereof, in particular in the form of alkali metal or alkaline-earth metal, ammonium or amino alcohol salts .

Preferably, the anionic surfactants (a) are chosen from salts, in particular salts of alkali metals such as sodium salts, ammoniums salts, amino alcohol salts or the salts of alkaline earth metals for example magnesium salts, of C₈-C24 alkylsulfosuccinate, C₈-C24 dialkylsulfosuccinate and C₈-C24 alkyl ether sulfosuccinates .

More preferably, the anionic surfactants (a) are chosen from salts, in particular salts of alkali metals such as sodium salts, ammoniums salts, amino alcohol salts or the salts of alkaline earth metals for example magnesium salts of C₈-C24 alkyl ether sulfosuccinates.

The anionic surfactant(s) (a) are preferably present in the composition in an amount ranging from 0.1 % to 20% by weight, especially from 0.5 % to 10% by weight and better still from 1 % to 5% by weight relative to the total weight of the composition.

In a preferred embodiment, the composition of the invention does not comprise anionic surfactant of sulfate type such as alkylsulfate and/or alkylethersulfate.

Hydroxyhydrocarbyl (poly)glycoside(s) (b)

The term “hydroxyhydrocarbyl (poly)glycoside” denotes a hydroxyhydrocarbyl polyglycoside or a hydroxyhydrocarbyl monoglycoside, also referred to in the present patent application as hydroxyhydrocarbyl glycoside. It comprises one or more glycoside ring bearing directly or through a divalent group, preferably directly, one or more hydrocarbon groups substituted by one or more hydroxy groups, said divalent group being optionally substituted. Said hydrocarbon group may be interrupted with one or more heteroatoms such O and/or N. Said hydroxyhydrocarbyl glycoside may be alkoxylated with one or more alkylene oxide groups, preferentially of C2-C4.

Preferably the hydroxyhydrocarbyl (poly)glycoside is a hydroxyalkyl (poly)glycoside.

The hydroxyhydrocarbyl (poly)glycoside (b) used, alone or as mixtures, in accordance with the present invention may be represented by the following general formula:

RiO-(R₂O)_t- (G)_v (I) in which:

- Ri represents : o a linear or branched alkyl or alkenyl group comprising 1 to 12 carbon atoms and especially 1 to 6 carbon atoms substituted by one or more hydroxyl group(s), or o a saturated or unsaturated heterocyclic group comprising 5 to 10 carbon atoms and one or more heteroatom such as O and N, and bearing one or more groups selected from hydroxy, linear or branched C1-C10, preferably Ci-Ce alkyl groups, ketone function, and mixtures thereof, said alkyl groups bearing one or more hydroxy groups ;

- R₂ represents an alkylene group comprising 2 to 4 carbon atoms,

- G represents a sugar unit comprising 5 to 6 carbon atoms,

- t denotes a value ranging from 0 to 10 and preferably 0 to 4,

- v denotes a value ranging from 1 to 15 and preferably 1 to 4.

Preferably, the hydroxyhydrocarbyl (poly)glycoside(s) (b) is(are) compound(s) of the formula described above in which:

- Ri denotes a linear or branched alkyl group comprising from 1 to 6 carbon atoms substituted by one or more hydroxyl group(s), or an unsaturated C5 or C6 heterocyclic group comprising O and bearing a ketone function, a hydroxy group and a dihydroxyethyl group, - R2 represents an alkylene group comprising 2 to 4 carbon atoms,

- t denotes a value ranging from 0 to 3 and preferably equal to 0,

- G denotes glucose, fructose or galactose, preferably glucose;

- the degree of polymerization, i.e. the value of v, possibly ranging from 1 to 15 and preferably from 1 to 4; the mean degree of polymerization more particularly being between 1 and 2.

The glucoside bonds between the sugar units are generally of 1 - 6 or 1 -4 type and preferably of 1 -4 type. Preferably, the hydroxyhydrocarbyl (poly)glycoside is an hydroxyhydrocarbyl (poly)glucoside.

Preferably, the hydroxyhydrocarbyl (poly)glycoside(s) is or are selected from: xylityl glucoside and xylityl polyglucoside of formula:

with x= l - 15, preferably 1 - 4 and ascorbyl glucoside of formula:

Xylityl glucoside having the above formula (II) wherein x = 1 is most particularly used in the composition of the invention. The hydroxyhydrocarbyl (poly)glycoside(s), preferably the hydroxyalkyl (poly)glycoside(s), (b) are present in a total amount ranging preferably from 0.01 % to 20% by weight, more preferably from 0.1 % to 10%, most preferably from 0.2% to 5%, and better from 0.5% to 3%, relative to the total weight of the composition.

Pyrrolidone carboxylic acid (PCA), its salts or its derivatives (c)

The composition of the invention comprises one or more compounds chosen from pyrrolidone carboxylic acid, salts thereof and derivatives thereof.

Pyrrolidone carboxylic acid (PCA) has the following formula:

As examples of salts, mention may be made of salts of alkaline metal such as sodium and potassium, of alkaline earth metal such as magnesium, of ammonium, or of aminoalcohol such as that defined above. Alkaline metal salts are particularly preferred, and more preferably, sodium salt of PCA is used:

The pyrrolidone carboxylic acid (PCA) derivatives may be selected from compounds of formula (III) :

wherein:

R3 is H, a C1-6 alkyl group, an alkaline metal such as sodium and potassium, an alkaline earth metal such as magnesium, an ammonium, or an aminoalcohol such as that defined above,

R4 is H, a C1-6 alkyl group, a C1-6 acyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, a carboxy group -COOR or an alkoxycarbonyl group -O-COR with R = C1-6 alkyl group, with at least one of R3 or R4 being different from H, and with the condition that when R3 is an alkaline metal, an alkaline earth metal, an ammonium, or an aminoalcohol, R4 is not H.

The alkyl group may be a linear, branched or cyclic alkyl group. Preferably the alkyl group is a linear or branched C1-6 alkyl group, more preferably C1-4 alkyl group, such as a methyl group, an ethyl group, a propyl group, an i-propyl group and a butyl group. On the other hand, the alkyl group may be a cyclic C3-6 alkyl group, such as cyclopentyl group or cyclohexyl group.

As examples of acyl group, there may be mentioned a C1-6 acyl group such as formyl group or acetyl group.

The C2-6 alkenyl group may be vinyl group, allyl group, butylene group, pentenyl group or hexenyl group .

Examples of C1-6 alkoxy group are methoxy group, ethoxy group and propoxy group.

The C1-6 alkoxycarbonyl group may be methoxycarbonyl group, ethoxycarbonyl group or propoxycarbonyl group.

The above substituent may be further substituted with at least one group such as a halogen atom, an amino group, a nitro group, a cyano group, a hydroxyl group and an aromatic group such as a phenyl group.

Preferably, the compound chosen from pyrrolidone carboxylic acid, salts thereof and derivatives thereof (c) is selected from pyrrolidone carboxylic acid salts, in particular sodium pyrrolidone carboxylate (PCA-Na or Sodium PCA) .

The compound(s) chosen from pyrrolidone carboxylic acid, salts thereof and derivatives thereof (c) are present in a total amount preferably ranging from 0.01 % to 20% by weight, more preferably from 0.02% to 10%, better from 0.05 % to 5%, better still from 0.1 to 3 % relative to the total weight of the composition.

The composition according to the invention may comprise water or a mixture of water and one or more cosmetically acceptable solvents chosen from C1-C4 alcohols, such as ethanol, isopropanol, tert-butanol or n-butanol; polyols such as glycerol, propylene glycol and polyethylene glycols ; and mixtures thereof. Preferably, the composition according to the invention has a total water content ranging from 60% to 99%, by weight, more preferably from 75 % to 98% by weight, better from 80% to 97 % by weight, and better still from 85 to 96% by weight, relative to the total weight of the composition.

Optional adjuvant( s )

The cosmetic composition of the invention may also contain various adjuvants conventionally used in hair compositions, selected from non-ionic surfactants different from the non-ionic surfactants (b) defined above, for example, polyalkoxylated fatty alcohols, poloxamers, polysorbates ; amphoteric surfactants, for example, coco betaines ; cationic surfactants, for example, cetrimonium chloride, behentrimonium chloride; volatile solvents, for example, lower viscosities dimethicone, cycloalkanes, volatile alkanes, esters; cationic polymers, for example, cationic guars or acrylamide copolymers ; thickeners ; fatty liquid components such as plant oils or mineral oils; and mixtures thereof.

The above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight, and preferably between 0.1 % and 20% by weight relative to the weight of the cosmetic composition of the invention.

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

In an embodiment, the total amount of surfactants including surfactants (a) and (b), in the composition according to the invention is less than 10 % by weight, more preferably less than 5 % by weight of the composition.

The present invention also relates to a cosmetic treatment process, especially for cleansing and conditioning keratin materials, in particular human keratin materials such as hair and skin, which consists in applying to the said keratin materials a cosmetic composition as described above, and after an optional leave-on time, optionally removing it by rinsing, for example with water.

The leave-on time of the composition on the keratin materials may range from a few seconds to 15 minutes, better still from 5 seconds to 10 minutes and even better still from 10 seconds to 5 minutes .

The composition may be applied to wet or dry keratin materials . Preferably, the cosmetic composition is not rinsed with water.

Finally, the present invention relates to the use of a cosmetic composition as described above for cleansing and conditioning keratin materials .

In the above description, all the preferred embodiments with regard to the components may be used individually or in combination.

The examples that follow serve to illustrate the invention.

Examples

In the examples that follow and unless otherwise indicated, the amounts are given as weight percentages of active material (AM) relative to the total weight of the composition.

Example 1

The following composition were prepared from the ingredients indicated in the table below.

These compositions could be used as leave-on cleanser; they performed parity to conventional shampoo in terms of cleansing. They give the hair a good clean feel and let hair individualized.

Further, these compositions are milder than conventional shampoos containing detersive surfactants .

These compositions when used as a leave-on can be advantageously a replacer to conventional shampoos, and do not necessitate the use of water (no rinse step) .

Example 2

The cleansing efficiency (sebum removal) was studied according to the following method with artificial sebum.

The composition of artificial sebum is as follows . The below components were diluted in 50 ml of heptane.

3 swatches of natural Indian hair, each weighing 1 g, were soaked in artificial sebum overnight, then removed and dried at room temperature (25°C). Each swatch of soiled hair was weighed. About 6 mg of sebum were deposited on each swatch.

0.4 g of composition 1 of example 1 was applied on each soiled hair swatch, followed by wiping with wet tissue paper (wet tissue wipe), 3 times front side and 3 times back side. The percentage of sebum removal for each treated hair swatch was then quantified in the following way: - the treated swatch was cut in pieces of approximately 0.5 cm length,

- 100 mg of cut hair swatch were weighed and 1 ml heptane added, the extraction with heptane was performed using a thermomixer, at 1500 rpm, for 3 hours at room temperature,

- the analysis of solution was performed on gas chromatographyflame ionization detector (GC-FID) to quantify the sebum remaining on the treated hair.

A comparative composition containing 3 % by weight of sodium laureth ( 1 unit of ethylene oxide) sulfate (SLES) in water was applied to other soiled swatches in the same manner as that used for composition 1.

The test was done in triplicate for each tested composition.

It has been observed that % sebum removal from soiled hair swatches cleansed with composition 1 is 92.37 ± 0.75%, whereas the %. sebum removal from soiled hair swatches cleansed with the comparative composition is 82.08 ± 0.21 % .

Therefore, the composition according to the invention (composition 1 ) is more effective in cleansing soiled hair when compared to the comparative composition comprising a conventional anionic surfactant SLES .

Example 3

The mildness of composition 2 of example 1 was evaluated using then zein protein solubility test, and compared to that of a comparative composition comprising 1.5 % by weight of sodium lauryl sulfate (SLS) in water.

Zein is a yellow corn protein which may be denatured and solubilized in water after contact with a surfactant. The ability of surfactant to denature and solubilize zein has been linked to their mildness potential. Lower the % of solubilized zein, milder the composition.

The following protocol was used to evaluate the mildness : 100 ml of an aqueous solution ( 1.5 % w/w) of sodium lauryl sulfate or of the composition to test were prepared;

10.0 ml of the above solutions were withdrawn using a micropipette and maintained as blanks for the respective samples ;

1.0 g of zein was added to the remaining 90 ml of each solution and equilibrated for 45 mins with constant stirring at 200 rpm, the supernatant solutions were filtered through a 0.45 pm nylon filter;

20 pl of the sample solution were diluted to 1 ml using water and mixed thoroughly;

400 pl of 2X Lowry concentrate were added, mixed and let at 25 °C for 10 minutes ;

400 pl of 0.2 N Folin reagent were added, mixed and let at 25 °C for 30 minutes ; the absorbance of the solutions was measured at 750 nm with an Infinite M200 PRO Multimode Microplate Reader from Tecan using 96 well plates ; and the %Zein score was calculated as follows :

Sample net absorbance @750 nm = Azso™ Sample - Azscnm Blank

% Ze in Score

Sample net absorbance x 100 SLS net absorbance

17.76 % of solubilized zein were obtained with composition 2 whereas 100 % were obtained with the comparative composition containing SLS .

Claims

1. Cosmetic composition comprising:

(a) one or more anionic surfactants of sulfosuccina(ma)te type,

(b) one or more hydroxyhydrocarbyl (poly)glycosides, and

(c) one or more compounds chosen from pyrrolidone carboxylic acid (PCA), salts thereof and derivatives thereof.

2. Cosmetic composition according to claim 1 , wherein the anionic surfactant(s) (a) are chosen from alkylsulfosuccinates, dialkyl sulfo succinates, alkyl ether sulfosuccinates, alkylamido sulfo succinates, alkylamido ether sulfosuccinates, alkylsulfosuccinamates, di alkylsulfosuccinamates, alkyl ether sulfosuccinamates and salts thereof, the alkyl groups comprising from 6 to 30 carbon atoms, especially from 8 to 24, better still from 10 to 20 carbon atoms, these compounds being optionally polyoxyalkylenated, especially polyoxyethylenated; better from Cs-C₂4 and especially Cio-C₂o alkylsulfosuccinates, Cs-C₂4 especially Cio-C₂o dialkylsulfosuccinate and Cs-C₂4 and especially Cio- C₂o alkyl ether sulfosuccinates, in particular in the form of alkali metal or alkaline-earth metal, ammonium or amino alcohol salts.

3. Cosmetic composition according to claim 1 or 2, wherein the anionic surfactant(s) (a) are present in the composition in an amount ranging from 0.1 % to 20% by weight, especially from 0.5% to 10% by weight and better still from 1 % to 5% by weight relative to the total weight of the composition.

4. Cosmetic composition according to any one of claims 1 to 3, wherein the hydroxyhydrocarbyl (poly)glycoside(s) (b) are represented by the following general formula:

RiO-(R₂O)_t- (G)_v (I) in which:

- Ri represents : o a linear or branched alkyl or alkenyl group comprising 1 to 12 carbon atoms and especially 1 to 6 carbon atoms substituted by one or more hydroxyl group(s), or o a saturated or unsaturated heterocyclic group comprising 5 to 10 carbon atoms and one or more heteroatom such as O and N, and bearing one or more groups selected from hydroxy, linear or branched Ci-Cio, preferably Ci-Ce alkyl groups, ketone function, and mixtures thereof, said alkyl groups bearing one or more hydroxy groups ;

- R2 represents an alkylene group comprising 2 to 4 carbon atoms,

- G represents a sugar unit comprising 5 to 6 carbon atoms,

- t denotes a value ranging from 0 to 10 and preferably 0 to 4,

- v denotes a value ranging from 1 to 15 and preferably 1 to 4.

5. Cosmetic composition according to any one of claims 1 to 4, wherein the hydroxyhydrocarbyl (poly)glycoside(s) (b) are chosen from xylityl glucoside, xylityl polyglucoside ascorbyl glucoside and especially xylityl glucoside.

6. Cosmetic composition according to any one of claims 1 to 5, wherein the hydroxyhydrocarbyl (poly)glycoside(s) (b) are present in a total amount ranging from 0.01 % to 20% by weight, preferably from 0.1 % to 10% , more preferably from 0.5 % to 3%, relative to the total weight of the composition.

7. Cosmetic composition according to any one of claims 1 to 6, wherein the pyrrolidone carboxylic acid derivatives have the following formula (III) :

wherein:

R3 is H, a C1-6 alkyl group, an alkaline metal such as sodium and potassium, an alkaline earth metal such as magnesium, an ammonium, or an aminoalcohol, 16

R4 is H, a C1-6 alkyl group, a C1-6 acyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, a carboxy group -COOR or an alkoxycarbonyl group -O-COR with R = C1-6 alkyl group with at least one of R3 or R4 being different from H, with the condition that when R3 is an alkaline metal, an alkaline earth metal, an ammonium, or an aminoalcohol, R4 is not H.

8. Cosmetic composition according to any one of claims 1 to 7, wherein the compound (c) is sodium pyrrolidone carboxylate.

9. Cosmetic composition according to any one of claims 1 to 8, wherein the compound(s) chosen from pyrrolidone carboxylic acid, salts thereof, and derivatives thereof (c) are present in a total amount ranging from 0.01 % to 20% by weight, preferably from 0.05% to 10%, more preferably from 0.1 % to 3%, relative to the total weight of the composition.

10. Cosmetic composition according to any one of claims 1 to 9, wherein the total amount of surfactants including surfactants (a) and (b), in the composition is less than 10 % by weight, more preferably less than 5 % by weight of the composition.

11. Cosmetic treatment process, especially for cleansing and conditioning keratin materials, in particular human keratin materials such as hair and skin, consisting in applying to the said keratin materials a cosmetic composition according to any one of the preceding claims, and after an optional leave-on time, optionally removing it by rinsing, for example with water.

12. Cosmetic treatment process according to claim 1 1 , wherein the cosmetic composition is not rinsed with water.

13. Use of a cosmetic composition according to any one of claims 1 to 10, for cleansing and conditioning keratin materials .