WO2022041217A1

WO2022041217A1 - A composition for caring for keratin materials

Info

Publication number: WO2022041217A1
Application number: PCT/CN2020/112580
Authority: WO
Inventors: Fan Wang; Xiaoming Wu; Xiuxia Wang; Qingsheng Tao
Original assignee: L'oreal
Priority date: 2020-08-31
Filing date: 2020-08-31
Publication date: 2022-03-03
Also published as: FR3113590A1; FR3113590B1; CN116437894A

Abstract

It relates to a composition in the form of oil-in-water emulsion for caring for keratin materials comprising: a) ferulic acid; b) at least one polar oil; c) at least one compound selected from saccharides and sugar alcohols; d) at least one surfactant; and e) at least one saturated C12-C26 fatty alcohol. It also relates to a process for caring for keratin materials, comprising applying the composition to the keratin materials.

Description

A COMPOSITION FOR CARING FOR KERATIN MATERIALS

TECHNICAL FIELD

The present invention relates to a composition for caring for keratin materials such as the skin, in particular the face. The present invention also relates to a process for caring for keratin materials such as the skin, in particular the face.

BACKGROUND

Ferulic acid and its esters have long been recognized for their activity to the skin. Ferulic acid is a robust antioxidant active agent which could provide whitening/lightening, anti-inflammation and UV protection benefits.

Efforts have been made to develop cosmetic products comprising ferulic acid.

US20140107046 discloses synergistic aqueous compositions comprising at least one flavonoid, and ferulic acid, and optionally one or more additional antioxidant, for cosmetic use.

However, ferulic acid is insoluble in water. Ferulic acid undergoes a decarboxylation reaction, resulting in a loss in the stability of ferulic acid and an unpleasant odour when contacting with water after several days, for example 7 days when the content of ferulic acid is no less than 1.9 wt. %, 15 days when the content of ferulic acid is no less than 1.5 wt. %, and 30 days when the content of ferulic acid is no less than 1.0 wt. %, relative to the composition containing it.

Some products focus on water-free cosmetic base to avoid contacting with water. These products deliver oily/greasy sensory and skin irritation which limits the application of ferulic acid in skin care field.

In order to improve the stability of ferulic acid in water, cosmetic formulations with a based mainly composed of siloxane and polyol were developed. US5824326 discloses a cosmetic composition comprising (i) 0.01wt. %to 5 wt. %of ferulic acid; (ii) from 0.1 wt. %to 20 wt. %of dimethyl isosorbide; and (iii) a pharmaceutically acceptable carrier, the carrier comprises a polyol in an amount from 1 wt. %to 50 wt. %of the composition and from 0.1 wt. %to 30 wt. %of a crosslinked non-emulsifying siloxane elastomer.

In aqueous system, the stability of ferulic acid can be improved by a polymer. WO2016/101135 discloses an oil-in-water emulsified composition comprising at least one polymer derived from 2-acrylamidomethylpropanesulfonic acid, at least one extract of a plant in the family Paeoniaceae, and at least one whitening agent, the whitening agent can be ferulic acid.

There is still a need for aqueous cosmetic products comprising ferulic acid, which is stable, and has no discomfort feeling such as greasy and sticky and odor issue.

SUMMARY OF THE INVENTION

Thus, one object of the present is thus to provide an aqueous composition for caring for keratin materials such as the skin, in particular the face, which is stable, and has no discomfort feeling such as greasy and sticky and odor issue.

Still another object of the present invention is to provide a process for caring for keratin materials such as the skin, in particular the face.

Thus, according to one aspect, the present invention provides a composition in the form of oil-in-water emulsion for caring for keratin materials comprising:

a) ferulic acid;

b) at least one polar oil;

c) at least one compound selected from saccharides and sugar alcohols;

d) at least one surfactant; and

e) at least one saturated C ₁₂-C ₂₆ fatty alcohol.

The composition according to the present invention has an alpha-gel structure, i.e. has a lamellar phase, due to the presence of surfactant and saturated C ₁₂-C ₂₆ fatty alcohol.

Surprisingly, the inventors have found that ferulic acid is stabilized in the structured-emulsion according to the present invention.

In the present application, the stability is evaluated by testing the degradation of active ingredient (i.e. ferulic acid and optional additional active ingredients) .

In addition, the composition delivers good hydration effect in the presence of saccharides and/or sugar alcohols, and results in a good skin feeling in the presence of saccharides, sugar alcohols and C ₁₂-C ₂₆ fatty alcohol in the form of lamellar phase.

According to another aspect, the present invention provides is a process for caring for keratin materials, comprising applying the composition according to the present invention to the keratin materials.

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

DETAILED DESCRIPTION OF THE INVENTION

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

For the purposes of the present invention, the term “keratin material” is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.

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

The term “and/or” used herein refers to one or all of the elements mentioned.

Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term “about” . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to, the definition described herein shall apply.

All percentages in the present application refer to weight percentage, unless otherwise specified.

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones.

As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. “consisting of” ) .

The composition according to the present invention comprises:

a) ferulic acid;

b) at least one polar oil;

c) at least one compound selected from saccharides and sugar alcohols;

d) at least one surfactant; and

e) at least one saturated C ₁₂-C ₂₆ fatty alcohol.

Ferulic acid

The composition according to the present invention comprises ferulic acid as an active ingredient.

Ferulic acid, CAS number of which is 1135-24-6, is also called 4-Hydroxy-3-methoxycinnamic acid, which has the following formula:

Ferulic acid can be broadly found in giant fennel, the seeds of coffee, apple, artichoke, peanut, and orange, as well as in both seeds and cell walls of commelinid plants (such as rice, wheat, oats, and pineapple) . Like many natural phenols, it is a strong antioxidant that is very reactive toward free radicals and reduces oxidative stress. Many studies suggest that ferulic acid may have antitumor activity.

Mention may be made of such product, for example, ORYZA FERULIX from ORYZA OIL&FAT CHEMICAL.

Preferably, the composition of the present invention comprises from 0.01 wt. %to 4 wt. %, preferably from 0.1 wt. %to 3.0 wt. %of ferulic acid, relative to the total weight of the composition.

Polar oil

The composition according to the present invention comprises at least one polar oil.

Preferably, the solubility of ferulic acid in 100g of the polar oil is no less than 1g. The polar oil is immiscible with water.

The term “polar oil” means any lipophilic compound having, at 25℃, a solubility parameter δ _d characteristic of dispersive interactions of greater than 16 and a solubility parameter δ _p characteristic of polar interactions strictly greater than 0. The solubility parameters δ _d and δ _p are defined according to the Hansen classification. For example, these polar oils may be selected from esters, and ethers.

The definition and calculation of the solubility parameters in the Hansen three-dimensional solubility space are described in the article by C.M. Hansen: “The three dimensional solubility parameters” , J. Paint Technol. 39, 105 (1967) .

According to this Hansen space:

- δ _d characterizes the London dispersion forces derived from the formation of dipoles induced during molecular impacts;

- δ _p characterizes the Debye interaction forces between permanent dipoles and also the Keesom interaction forces between induced dipoles and permanent dipoles;

- δ _h characterizes the specific interaction forces (such as hydrogen bonding, acid/base, donor/acceptor, etc. ) ; and

- δ _a is determined by the equation: δ _a= (δ _p ²+δ _h ²) ^1/2.

The parameters δ _p, δ _h, δ _d, and δ _a are expressed in (J/cm ³) ^1/2.

The polar oil may be a volatile or non-volatile hydrocarbon-based oil.

These oils may be of plant, mineral, or synthetic origin.

The term “polar hydrocarbon-based oil” means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms. It may contain alcohol, ester, ether, carboxylic acid, amine, and/or amide groups.

Preferentially, the polar oil according to the invention has a surface tension greater than 10mN/m at 25℃ and under atmospheric pressure.

The surface activity is measured by static tensiometry using the Du Noüy ring.

The principle of the measurement is as follows (measurement carried out at 25℃and atmospheric pressure) :

The weight of the ring is neutralized by a tare. The ring is completely immersed in the liquid to be evaluated, then withdrawn very slowly until the force reaches its maximum. From this maximum force F _max, the surface tension is calculated according to the equation:

σ=F _max/4πR f _corr (r, R, ρ)

with f _corr: correction factor of the ring depending on the geometry of the ring and the densityρ.

The parameters r and R respectively denote the internal and external radii of the ring.

According to a first embodiment, the polar oil may be a non-volatile oil. In particular, the non-volatile polar oil may be selected from the list of oils below, and mixtures thereof:

- hydrocarbon-based polar oils such as phytostearyl esters, such as phytostearyl oleate, phytostearyl isostearate, and lauroyl/octyldodecyl/phytostearyl glutamate (Ajinomoto, Eldew PS203) , triglycerides consisting of fatty acid esters of glycerol, in particular the fatty acids of which may have chain lengths ranging from C ₄to C ₃₆, and especially from C ₁₈ to C ₃₆, these oils possibly being linear or branched, and saturated or unsaturated; these oils may especially be heptanoic or octanoic triglycerides, wheat germ oil, sunflower oil, grape seed oil, sesame seed oil (820.6 g/mol) , corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil, or musk rose oil; shea butter; or alternatively caprylic/capric acid triglycerides, for instance those sold by the company Stéarineries Dubois or those sold under the names Miglyol

and

by the company Dynamit Nobel;

- synthetic ethers containing from 10 to 40 carbon atoms, such as dicaprylyl ether;

- hydrocarbon-based esters of formula RCOOR’ in which RCOO represents a carboxylic acid residue comprising from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, such as cetostearyl octanoate, isopropyl alcohol esters, such as isopropyl myristate or isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, diisopropyl adipate, heptanoates, and especially isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, for instance propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, 2-ethylhexyl 4- diheptanoate, and palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol 2-diethyl hexanoate, and mixtures thereof, C ₁₂ to C ₁₅ alcohol benzoates, hexyl laurate, neopentanoic acid esters, for instance isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, and 2-octyldodecyl neopentanoate, isononanoic acid esters, for instance isononyl isononanoate, isotridecyl isononanoate, and octyl isononanoate, oleyl erucate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate, and myristyl myristate;

- polyesters obtained by condensation of an unsaturated fatty acid dimer and/or trimer and of diol, such as those described in patent application FR 0 853 634, in particular such as dilinoleic acid and 1, 4-butanediol. Mention may especially be made in this respect of the polymer sold by Biosynthis under the name Viscoplast 14436H (INCI name: dilinoleic acid/butanediol copolymer) , or else copolymers of polyols and of dimer diacids, and esters thereof, such as Hailuscent ISDA;

- polyol esters and pentaerythritol esters, for instance dipentaerythrityl tetrahydroxystearate/tetraisostearate;

- fluorinated oils which are optionally partially hydrocarbon-based and/or silicone-based;

- fatty acids containing from 12 to 26 carbon atoms, for instance oleic acid;

- dialkyl carbonates, the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate sold under the name Cetiol

by Cognis; and

- non-volatile oils of high molecular mass, for example between 400 and 10 000 g/mol, in particular between 650 and 10000g/mol, for instance:

i) vinylpyrrolidone copolymers such as the vinylpyrrolidone/1-hexadecene copolymer, Antaron V-216 sold or manufactured by the company ISP (MW=7300 g/mol) ,

ii) esters such as:

a) linear fatty acid esters with a total carbon number ranging from 35 to 70, for instance pentaerythrityl tetrapelargonate (MW=697.05 g/mol) ,

b) hydroxylated esters such as polyglycerol-2 triisostearate (MW=965.58 g/mol) ,

c) aromatic esters such as tridecyl trimellitate (MW=757.19 g/mol) , C ₁₂-C ₁₅ alcohol benzoate, 2-phenylethyl benzoate, and butyloctyl salicylate,

d) esters of C ₂₄-C ₂₈ branched fatty acids or fatty alcohols such as those described in patent application EP-A-0955039, and especially triisoarachidyl citrate (MW=1033.76 g/mol) , pentaerythrityl tetraisononanoate (MW=697.05 g/mol) , glyceryl triisostearate (MW=891.51g/mol) , glyceryl tris (2-decyl) tetradecanoate (MW=1143.98g/mol) , pentaerythrityl tetraisostearate (MW=1202.02 g/mol) , polyglyceryl-2 tetraisostearate (MW=1232.04 g/mol) or else pentaerythrityl tetrakis (2-decyl) tetradecanoate (MW=1538.66 g/mol) ,

e) esters and polyesters of dimer diol and of monocarboxylic or dicarboxylic acid, such as esters of dimer diol and of fatty acid and esters of dimer diol and of dimer dicarboxylic acid, such as Lusplan

and Lusplan

sold by the company Nippon Fine Chemical and described in patent application US 2004-175 338, the content of which is incorporated into the present application by reference,

- and mixtures thereof.

Preferably the polar oil is selected from C ₁₂-C ₁₅ alcohol benzoate, diisopropyl sebacate, isopropyl lauroyl sarcosinate, dicaprylyl carbonate, 2-phenylethyl benzoate, butyloctyl salicylate, 2-octyldodecyl neopentanoate, dicaprylyl ether, dimethyl isosorbide, isocetyl stearate, isodecyl neopentanoate, isononyl isononate, isopropyl myristate, isopropyl palmitate, isostearyl behenate, myristyl myristate, octyl palmitate, tridecyl trimellitate, and castor oil.

Preferably, the polar oil is selected from isopropyl lauroyl sarcosinate, dimethyl isosorbide, and castor oil.

The amount of the polar oil can be adjusted based on the amount of ferulic acid in the composition.

Preferably, the composition of the present invention comprises from 1 wt. %to 50 wt. %, preferably from 2 wt. %to 20 wt. %of the polar oil, relative to the total weight of the composition.

Compound selected from saccharides and sugar alcohols

The composition according to the present invention comprises at least one compound selected from saccharides and sugar alcohols.

Preferably, the solubility of ferulic acid in 100g of the compound selected from saccharides and sugar alcohols is less than 0.5 g.

The compound selected from saccharides and sugar alcohols is miscible with water.

As examples of suitable sugar alcohols, mention can be made of glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, volemitol, isomalt, maltitol, lactitol, maltotriitol, maltotetraitol, and polyglgycitol.

As examples of suitable saccharide, mention can be made of monosaccharides such as glucose, fructose, galactose, xylose, rhamnose, fucose, arabinose, ribose, sorbose, tagatose, psicose, allose, idose, and talose, and disaccharides such as mannose, sucrose, maltose, lactose, trehalose, cellobiose, chitobiose, kojibiose, nigerose, isomaltose, sophorose, laminaribiose, gentiobiose, trehalulose, turanose, maltulose, isomaltulose, gentiobiulose, mannobiose, melibiose, melibiulose, rutinose, rutinulose, and xylobiose.

Furthermore, the composition according to the present invention will deliver good hydration effect in the presence of saccharides and sugar alcohols, and results in a good skin feeling in the presence of fatty alcohols, sugar alcohols and saccharides.

Preferably, the composition of the present invention comprises 1 wt. %to 50 wt. %, preferably from 5 wt. %to 45 wt. %, of the compound selected from saccharides and sugar alcohols, relative to the total weight of the composition.

Surfactants

The composition of the present invention comprises at least one surfactant.

The surfactant is not limited, and can be selected from amphoteric or zwitteronic surfactants, cationic surfactants, anionic surfactants, nonionic surfactants, and a mixture thereof.

In some preferred embodiments, the composition according to the present invention includes one or more amino acid surfactants. In particular, the amino acid surfactants include those derived from taurate, glutamate, alanin or alaninate, sarcosinate and aspartate. Amino acid surfactants typically have the following structure:

wherein R ³ is a saturated or unsaturated, straight or branched alkyl chain with 7 to 17 C atoms, R ⁴ is H or a methyl, R ⁵ is H, COO ^-M ⁺, CH ²COO ^-M or COOH, m is 0 to 2, X is COO ^- or SO ₃ ^- and M is independently H, sodium, potassium or ammonium. In some instances, R ³ is a saturated or unsaturated, straight or branched alkyl chain with 9 to 17 C atoms, or 9 to 13 C atoms, R ⁴ is H or a methyl, R ⁵ is H, COOM ⁺, CH ₂COOM or COOH, m is 0 to 2, X is COO or SO ₃and M is independently H, sodium or potassium.

Non-limiting examples of amino acid surfactants include potassium cocoyl taurate, potassium methyl cocoyl taurate, sodium caproyl methyl taurate, sodium cocoyl taurate, sodium lauroyl taurate, sodium methyl cocoyl taurate, sodium methyl lauroyl taurate, sodium methyl myristoyl taurate, sodium methyl oleoyl taurate, sodium methyl palmitoyl taurate, sodium methyl stearoyl taurate, dipotassium capryloyl glutamate, dipotassium undecylenoyl glutamate, disodium capryloyl glutamate, disodium cocoyl glutamate, disodium lauroyl glutamate, disodium stearoyl glutamate, disodium undecylenoyl glutamate, potassium capryloyl glutamate, potassium cocoyl glutamate, potassium lauroyl glutamate, potassium myristoyl glutamate, potassium stearoyl glutamate, potassium undecylenoyl glutamate, sodium capryloyl glutamate, sodium cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, sodium olivoyl glutamate, sodium palmitoyl glutamate, sodium stearoyl glutamate, sodium undecylenoyl glutamate, cocoyl methyl β-alanine, lauroyl β-alanine, lauroyl methyl β-alanine, myristoyl β-alanine, potassium lauroyl methyl β-alanine, sodium cocoyl alaninate, sodium cocoyl methyl β-alanine and sodium myristoyl methyl β-alanine palmitoyl glycine, sodium lauroyl glycine, sodium cocoyl glycine, sodium myristoyl glycine, potassium lauroyl glycine, potassium cocoyl glycine, potassium lauroyl sarcosinate, potassium cocoyl sarcosinate, sodium cocoyl sarcosinate, sodium lauroyl sarcosinate, sodium myristoyl sarcosinate, and sodium palmitoyl sarcosinate and mixtures thereof.

Particular mention may be made of potassium cocoyl taurate, potassium methyl cocoyl taurate, sodium caproyl methyl taurate, sodium cocoyl taurate, sodium lauroyl taurate, sodium methyl cocoyl taurate, sodium methyl lauroyl taurate, sodium methyl myristoyl taurate, sodium methyl oleoyl taurate, sodium methyl palmitoyl taurate, sodium methyl stearoyl taurate, and mixtures thereof.

Preferably, the composition of the present invention comprises from 0.05 wt. %5 wt. %, preferably from 0.1 wt. %to 3.0 wt. %of the surfactant, relative to the total weight of the composition.

Saturated C ₁₂-C ₂₆ fatty alcohols

The composition according to the present invention comprises at least one saturated C ₁₂-C ₂₆fatty alcohol.

For the purposes of the invention, the saturated C ₁₂-C ₂₆fatty alcohols are linear, and saturated or unsaturated. Preferably, the fatty alcohols comprise from 14 to 22 carbon atoms.

The fatty alcohol (s) that are suitable for use in the invention are preferably selected from cetyl alcohol, stearyl alcohol, cetylstearyl alcohol, myristyl alcohol, lauryl alcohol, tridecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, arachidyl alcohol, behenyl alcohol and myricyl alcohol; they are preferably selected from cetyl alcohol, stearyl alcohol and cetylstearyl alcohol.

As cetyl alcohols that may be most particularly suitable for use in the invention, use may be made, for example, of the products sold under the names

16/98 F and

16/98 P sold by the company Ecogreen Oleochemicals,

16 soldby the company Evonik Goldschmidt,

16 sold by the company Cognis,

1698 sold by the company VVF,

1698 P sold by the company Oxiteno, Cetyl Alcohol 98%Min sold by the company Emery Oleochemicals,

16 (98%) sold by the company Godrej Industries,

16-98 sold by the company Sasol,

6098 sold by the company Kao, and

16 sold by the company Aegis Chemical.

As stearyl alcohols that are most particularly suitable for use in the invention, use may be made, for example, of those sold under the names

18 sold by the company Evonik Goldschmidt,

18/98 F and

18/98 P sold by the company Ecogreen Oleochemicals,

18 sold by the company Cognis,

8098 sold by the company Kao,

18 sold by the company Aegis Chemical,

18-98 sold by the company Sasol and

45 sold by the company Nihon Yushi.

As cetylstearyl alcohols that are most particularly suitable for use in the invention, use may be made, for example, of those sold under the names

68/50 F and

68/50 P sold by the company Ecogreen Oleochemicals,

O OR and

O OR Flakes sold by the company Cognis,

1618 C50 P sold by the company Oxiteno,

16-18 EN sold by the company Sasol, Alcohol Cetoestearilico 50/50 sold by the company Industria Quimica Del Centro,

30 CK sold by the company New Japan Chemical, Cetylstearyl Alcohol 50: 50 sold by the company Evonik Goldschmidt,

6850 sold by the company Kao,

1618 (50: 50) sold by the company VVF and

1618 50: 50 OR sold by the company Godrej Industries.

The lamellar structure constructed with solid fatty alcohol and surfactant provides another physical barrier between the oil phase containing ferulic acid and the hydrous phase.

Preferably, the composition of the present invention comprises from 0.5 wt. %to 25 wt. %, preferably from 1 wt. %to 10 wt. %of the saturated C ₁₂-C ₂₆fatty alcohol, relative to the total weight of the composition.

Oil phase

The composition according to the present invention comprises an oil phase.

In addition to polar oils mentioned previously, the oil phase may comprise an additional oil.

In particular, the additional oil may be selected from nonvolatile apolar hydrocarbon-based oils and volatile oils, in particular volatile hydrocarbon-based oils (e.g. squalene) , volatile silicone oils (e.g. dimethicone, stearyl dimethicone) , volatile fluoro oils, mineral oils.

According to an embodiment, a nonvolatile apolar hydrocarbon-based oil is contained as an additional oil.

For the purposes of the present invention, the term “apolar oil” means an oil whose solubility parameter at 25℃., δ _a, is equal to 0 (J/cm ³) ^1/2.

Preferably, the nonvolatile apolar hydrocarbon-based oil is free of oxygen atoms.

Preferably, the nonvolatile apolar hydrocarbon-based oil may be selected from linear or branched hydrocarbons of mineral or synthetic origin, such as:

liquid paraffin or derivatives thereof,

liquid petroleum jelly,

naphthalene oil,

polybutylenes such as Indopol H-100 (molar mass or MW=965 g/mol) , Indopol H-300 (MW=1340 g/mol) and Indopol H-1500 (MW=2160 g/mol) sold or manufactured by the company Amoco,

hydrogenated polyisobutylenes such as

sold by the company Nippon Oil Fats, Panalane H300 E sold or manufactured by the company Amoco (MW=1340 g/mol) , Viseal 20000 sold or manufactured by the company Synteal (MW=6000 g/mol) and Rewopal PIB 1000 sold or manufactured by the company Witco (MW=1000 g/mol) ,

decene/butene copolymers, polybutene/polyisobutene copolymers, especially Indopol L-14,

polydecenes and hydrogenated polydecenes such as: Puresyn 10 (MW=723 g/mol) and Puresyn 150 (MW=9200 g/mol) sold or manufactured by the company Mobil Chemicals,

and mixtures thereof.

Hydrous phase

The composition according to the present invention comprises a hydrous phase.

The aqueous phase comprises water.

The aqueous part may also comprise water-miscible organic solvents (at room temperature: 25℃) , for instance monoalcohols containing from 2 to 6 carbon atoms, such as ethanol or isopropanol, and mixtures thereof.

Advantageously, the composition according to the present invention may comprise a hydrous phase in an amount ranging from 40 wt. %to 95 wt. %, preferably from 45 wt. %to 85 wt. %, relative to the total weight of the composition.

Thickeners

According to some embodiments, the composition according to the present invention further comprises at least one lipophilic thickener and/or hydrophilic thickener.

Lipophilic thickener

The hydrophobic thickener may be selected from mineral thickeners especially such as organophilic clays; hydrophobic fumed silicas; hydrophobic silica aerogels; from organic thickeners such as oil-gelling polymers of the block polymer type, especially triblock or star polymers, resulting from the copolymerization of at least one styrene monomer and of at least one hydrocarbon monomer bearing one or two C ₂-C ₅ ethylenic unsaturations, such as ethylene, propylene, butadiene, isoprene and/or pentadiene, such as the polymers sold under the name Kraton; polyamide resins, such as those described in US-A-5 783 657; polyurethanes (e.g., polyurethane-79) ; modified cellulose (e.g. methylcellulose and ethylcellulose) ; polysaccharide alkyl ethers, especially in which the alkyl group is of C ₁-C ₂₄, preferably C ₁-C ₁₀ and better still C ₁-C ₆, described especially in EP 898 958, and in particular alkyl guar gums (with a C ₁-C ₆ alkyl group) , such as those described in EP 708 114; esters of dextrin and of a fatty acid, preferably of C ₁₂ to C ₂₄, in particular C ₁₄-C ₁₈, for example dextrin palmitate and dextrin myristate; N-acylglutamides in which the acyl group is a linear or branched C ₈ to C ₂₂ alkyl chain; preferably dialkyl N-acylglutamides, for instance lauroylglutamic acid dibutylamide or N-2-ethylhexanoyl glutamic acid dibutylamide; hydroxystearic acid; ethylenediamine stearyl dimer dilinoleate copolymer (sold, for example, under the name Oleocraft by Croda) ; and also mixtures thereof.

Clays are silicates containing a cation that may be selected from calcium, magnesium, aluminium, sodium, potassium and lithium cations, and mixtures thereof. Examples of such products that may be mentioned include clays of the smectite family such as montmorillonites, hectorites, bentonites, beidellites and saponites, and also of the family of vermiculites, stevensite and chlorites. These clays may be of natural or synthetic origin. Organophilic clays are clays modified with a chemical compound selected from quaternary amines, tertiary amines, amine acetates, imidazolines, amine soaps, fatty sulfates, alkyl aryl sulfonates and amine oxides, and mixtures thereof.

Mention may thus be made of hectorites modified with a quaternary amine, more specifically with a C ₁₀ to C ₂₂ fatty acid ammonium halide, such as a chloride, such as hectorite modified with distearyldimethylammonium chloride (CTFA name: Disteardimonium hectorite) , for instance the product sold under the name Bentone

Bentone 38V CG or Bentone EW CE by the company Elementis, or stearalkonium hectorites, such as Bentone 27 V.

Mention may also be made of quaternium-18 bentonites, such as those sold under the names Bentone 34 by the company Elementis, Tixogel VP by the company United Catalyst and Claytone 40 by the company Southern Clay; stearalkonium bentonites, such as those sold under the names Tixogel LG by the company United Catalyst and Claytone AF and Claytone APA by the company Southern Clay; or quaternium-18/benzalkonium bentonites, such as that sold under the name Claytone HT by the company Southern Clay.

The polyamide can be used in the present invention includes aliphatic polyamides, for example polyamide-4, polyamide-6, polyamide-8, polyamide-11, polyamide-12, polyamide-4, 6, polyamide-6, 6, polyamide-6, 9, polyamide-6, 10, and polyamide-6, 12; polyamides derived from an aliphatic diamine and an aromatic dicarboxylic acid, for example polyamide-4, T, polyamide-6, T, polyamide-4, I, etc., in which T stands for terephthalate and I stands for isophthalate; copolyamides of linear polyamides and copolyamides of an aliphatic and a partially aromatic polyamide, for example 6/6, T, 6/6, 6/6, T, as well as amorphous polyamides of the

PA 6-3-T and

TR 55 types.

Preferably, the polyamides are selected from aliphatic polyamides, such as polyamide-4, polyamide-6, polyamide-8, polyamide-11, polyamide-12, polyamide-4, 6, polyamide-6, 6, polyamide-6, 9, and polyamide-6, 10, polyamide-6, 12.

The hydrophobic fumed silicas may be obtained by modification of the surface of the silica via a chemical reaction that generates a reduction in the number of silanol groups, these groups possibly being substituted especially with hydrophobic groups. The hydrophobic groups may be:

- trimethylsiloxyl groups, which are obtained especially by treating fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are known as Silica silylate according to the CTFA (6th Edition, 1995) . They are sold, for example, under the references Aerosil

by the company Degussa, and Cab-O-Sil

by the company Cabot;

- dimethylsilyloxyl or polydimethylsiloxane groups, which are especially obtained by treating fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane. Silicas thus treated are known as Silica dimethyl silylate according to the CTFA (6th Edition, 1995) . They are sold, for example, under the references Aerosil

and Aerosil

by the company Degussa, and Cab-O-Sil

and Cab-O-Sil

by the company Cabot.

Silica aerogels are porous materials obtained by replacing (by drying) the liquid component of a silica gel with air. They are generally synthesized via a sol-gel process in a liquid medium and then dried, usually by extraction with a supercritical fluid, the one most commonly used being supercritical CO ₂. This type of drying makes it possible to avoid shrinkage of the pores and of the material. The sol-gel process and the various drying operations are described in detail in Brinker C.J. and Scherer G.W., Sol-Gel Science, New York: Academic Press, 1990.

Use will preferably be made of hydrophobic silica aerogel particles surface-modified with trimethylsilyl groups.

Hydrophobic silica aerogels that may be mentioned, for example, include the aerogel sold under the name VM-2260 (INCI name: Silica silylate) , by the company Dow Corning, the particles of which have a mean size of about 1000 microns and a specific surface area per unit mass ranging from 600 to 800 m ²/g. Mention may also be made of the aerogels sold by the company Cabot under the references Aerogel TLD 201, Aerogel OGD 201, Aerogel TLD 203,

Aerogel MT 1100 and Enova Aerogel MT 1200.

The elastomeric polyorganosiloxanes are generally partially or totally crosslinked and possibly of three-dimensional structure. The elastomeric polyorganosiloxanes combined with a fatty phase are generally in the form of a gel constituted of an elastomeric organopolysiloxane combined with a fatty phase, included in at least one hydrocarbon-based oil and/or one silicone oil. They may be selected especially from the crosslinked polymers described in patent application EP-A-0 295 886. According to said patent application, the elastomeric organopolysiloxanes are obtained by addition reaction and crosslinking of at least:

(a) one organopolysiloxane bearing at least two lower alkenyl groups per molecule;

(b) one organopolysiloxane bearing at least two hydrogen atoms linked to a silicon atom per molecule; and

(c) a platinum-type catalyst.

Preferably, the composition comprises at least one hydrophobic thickener selected from polyamides, polyurethanes, and ethylcellulose.

Ifpresents, the hydrophobic thickener may be present in a content ranging from 0.01 wt. %to 5 wt. %and preferably ranging from 0.05 wt. %to 1 wt. %, relative to the total weight of the composition.

Hydrophilic thickeners

Particularly, the hydrophilic thickener may be selected from:

- homopolymers or copolymers of acrylic or methacrylic acid or salts thereof and esters thereof. Examples that may be mentioned in particular include the products sold under the names Versicol F or Versicol K by the company Allied Colloid, Ultrahold 8 by the company Ciba-Geigy, Cosmedia SP by the company BASF, Lecigel (mixture of sodium acrylates copolymer/lecithin) by the company Lucas Meyer Cosmetics; polyacrylic acids of Synthalen K type, and salts, especially sodium salts, of polyacrylic acid (corresponding to the INCI name sodium acrylate copolymer) and more particularly a crosslinked sodium polyacrylate (corresponding to the INCI name sodium acrylate copolymer (and) caprylic/capric triglyceride) sold under the name Luvigel EM.

Mention may also be made of polyacrylic acid/alkyl acrylate copolymers, preferably modified or unmodified carboxyvinyl polymers, most particularly acrylate/C10-C30-alkyl acrylate copolymers (INCI name: Acrylate/C10-30 Alkyl Acrylate Crosspolymer) such as the products sold by the company Lubrizol under the trade names Pemulen TR1, Pemulen TR2, Carbopol 1382, Carbopol EDT 2020 and even more preferentially Pemulen TR-2; copolymers of methacrylic acid, of methyl methacrylate, of methylstyrene isocyanate and of PEG-40 behenate (INCI name: polyacrylate-3) (Viscophobe DB 1000 sold by the company Dow) ,

- copolymers of acrylic acid and of acrylamide sold in the form of the sodium salt thereof under the Reten names by the company Hercules, the sodium polymethacrylate sold under the name Darvan No. 7 by the company Vanderbilt, and the sodium salts of polyhydroxycarboxylic acids sold under the name Hydagen F by the company Henkel,

- homopolymers and copolymers based on acrylamidopropanesulfonic acid, for instance:

- polyacrylamidomethylpropanesulfonic acid partially neutralized with aqueous ammonia and highly crosslinked, for example the product Hostacerin AMPS sold in particular by the company Clariant,

- copolymers of acrylamidopropanesulfonic acid/acrylamide for example of Sepigel or Simulgel type sold especially by the company SEPPIC,

- polyoxyethylenated acrylamidopropanesulfonic acid/alkyl methacrylate copolymers (crosslinked or non-crosslinked) of the type such as, inter alia, Aristoflex HMS and Aristoflex TAC, sold by the company Clariant,

- copolymers of acrylamidomethylpropanesulfonic acid and of hydroxyethyl acrylate, for instance the acrylamidomethylpropanesulfonic acid/hydroxyethyl acrylate copolymer especially such as the product used in the commercial product sold under the name Simulgel NS by the company SEPPIC, or the acrylamido methylpropanesulfonic acid/hydroxyethyl acrylate copolymer especially such as the product used in the commercial product sold under the name Sepinov EMT 10 sold by the company SEPPIC (INCI name: Hydroxyethyl acrylate/sodium acryloyldimethyl taurate copolymer) ;

- copolymers of acrylamidomethylpropanesulfonic acid and of vinylpyrrolidone, such as the product Aristoflex AVC (ammonium acryloyldimethyl taurate/VP copolymer in water) sold by the company Clariant;

- and mixtures thereof.

Other examples of hydrophilic thickener that may be mentioned include:

- anionic, cationic, amphoteric or nonionic chitin or chitosan polymers;

- cellulose polymers, in particular (C ₁-C ₃) hydroxyalkylcelluloses, selected from hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydroxymethylcellulose, ethylhydroxyethylcellulose; carboxymethylcellulose;

- vinyl polymers, for instance polyvinylpyrrolidones, copolymers of methyl vinyl ether and of malic anhydride, the copolymer of vinyl acetate and of crotonic acid, copolymers of vinylpyrrolidone and of vinyl acetate; copolymers of vinylpyrrolidone and of caprolactam; polyvinyl alcohol,

- optionally modified polymers of natural origin, such as galactomannans and derivatives thereof, for instance konjac gum, gellan gum, locust bean gum, fenugreek gum, karaya gum, gum tragacanth, gum arabic, acacia gum, guar gum, hydroxypropyl guar, hydroxypropyl guar modified with sodium methylcarboxylate groups (Jaguar XC97-1, Rhodia) , xanthan gum and derivatives thereof;

- alginates and carrageenans;

- muccopolysaccharides such as hyaluronic acid;

- polyurethane, such as polyurethane-79;

- and mixtures thereof.

According to a preferred embodiment, the hydrophilic thickener is selected from optionally modified polymers of natural origin, polyurethane, and a mixture thereof.

If presents, the hydrophilic thickener is present in the composition according to the present invention in an amount ranging from 0.05wt. %to 3 wt. %, preferably from 0.1wt. %to 1.5 wt. %, relative to the weight of the composition.

Additional cosmetic active agent (s)

Depend on the final purpose, the composition can comprise an additional cosmetic active agent (s) in the oil phase and/or the hydrous phase depending on their nature.

As additional cosmetic active agents that may be used in the composition of the present invention, examples that may be mentioned include enzymes; flavonoids; moisturizers; anti-inflammatory agents; vitamins; depigmenting agents; whitening agents (such as phenylethyl resorcinol) ; α-hydroxy acids; β-hydroxy acids (such as capryloyl salicylic acid) ; retinoids; antibacterial active agents; tensioning agents; ceramides; essential oils; UV-screening agents (or sunscreens) , and mixtures thereof; and any other active agent that is suitable for the final purpose of the composition.

It is easy for the skilled in the art to adjust the amount of the additional cosmetic active agent based on the final use of the composition according to the present invention.

It is also easy for the skilled in the art to decide whether to add the additional cosmetic active agent (s) in the hydrous phase and/or the oil phase.

Adjuvants or additives

The composition according to the present invention may also contain conventional cosmetic adjuvants or additives, which will be in the hydrous phase and/or the oil phase depending on their nature, for instance fragrances, preserving agents and bactericides, opacifiers, dyes, softeners, buffers, electrolytes such as sodium chloride, or a pH regulator (for example citric acid or potassium hydroxide) , and mixtures thereof.

Preserving agents that may be used include any preserving agent usually used in the fields under consideration, for instance p-anisic acid, parabens, chlorphenesin, phenoxyethanol, chlorhexidine gluconate and polyhexamethylene biguanide hydrochloride (CTFA name: Polyaminopropyl biguanide) .

The preserving agent, when presents, generally represent from 0.1wt. %to 1.5 wt. %, preferably from 0.2 wt. %to 1.2 wt. %, relative to the total weight of the composition.

According to a preferred embodiment of the present invention, the composition contains a preserving agent selected from p-anisic acid, chlorphenesin, hydroxyacetophenone, and a mixture thereof.

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

It is easy for the skilled in the art to decide whether to add the adjuvant (s) in the hydrous phase and/or the oil phase.

According to a preferred embodiment, the present invention provides a composition in the form of oil-in-water emulsion for caring for keratin materials comprising, relative to the total weight of the composition:

a) from 0.1 wt. %to 3.0 wt. %of ferulic acid;

b) from 2 wt. %to 20 wt. %of at least one polar oil selected from isopropyl lauroyl sarcosinate, dimethylisosorbide, and castor oil;

c) from 5 wt. %to 45 wt. %of at least one compound selected from glycerine, mannose, sucrose, and sorbitol;

d) from 0.1 wt. %to 3.0 wt. %of at least one surfactant; and

e) from 1 wt. %to 10 wt. %of at least one saturated C ₁₂-C ₂₆ fatty alcohol selected from cetyl alcohol, stearyl alcohol and cetylstearyl alcohol.

Method and use

Another object of the present invention is to provide a process for caring for keratin materials.

The keratin materials include the skin, in particular the face.

The composition according to the present invention may be used for caring for keratin materials.

Thus, according to another aspect, the present invention provides a process for caring for keratin materials, comprising applying the composition according to the present invention to the keratin materials.

The examples that follow are aimed at illustrating the compositions according to the present invention, but not in any way a limitation of the scope of the present invention.

EXAMPLES

Example 1

Composition 1 comprising the ingredients shown in Table 1 was prepared, with all amounts expressed by percentages by weight of active matter with regard to the total weight of the composition.

Table 1

Preparation procedure:

The composition was prepared as follows:

1. ingredients in phase A were weighted in a main vessel, and ingredients in phase B were weighted in another vessel;

2. the ingredients in phase A and phase B were heated separately to 75℃ and stirred slowly until all ingredients dissolved or melted and clear solutions were formed;

3. phase B was added into phase A with stirring at 75℃ to form an emulsion; and

4. the emulsion was cooled down to room temperature with gentle stirring.

The composition obtained with the ingredients listed in Table 1 is in the form of a structured emulsion, which is within the scope of the present invention.

The degradation of ferulic acid (FA) in composition 1 after storage was tested and the results were summarized in Table 2.

Table 2

	Storage condition	FA Content, %	Degradation, %
Composition 1	45C for 2 months	0.49	2

Example 2

Following the procedure in Example 1, compositions 2-4 comprising the ingredients shown in Tables 3-5, respectively, were prepared, with all amounts expressed by percentages by weight of active matter with regard to the total weight of each composition.

Table 3: Composition 2

The composition obtained with the ingredients listed in Table 3 is in the form of a gel emulsion, which is out of the scope of the present invention.

Table 4: Composition 3

The composition obtained with the ingredients listed in Table 4 is in the form of a structured emulsion without sugar alcohols or saccharides, which is out of the scope of the present invention.

Table 5: Composition 4

The composition obtained with the ingredients listed in Table 5 is in the form of a structured emulsion and within the scope of the present invention.

The degradation of ferulic acid (FA) in compositions 2-4 after was storage tested and the results were summarized in Table 6.

Table 6

	Storage condition	FA Content, %	Degradation, %
Composition 2	45C for 2 months	0.45	10
Composition 3	45C for 2 months	0.47	6
Composition 4	45C for 2 months	0.49	2

Example 3

Following the procedure in Example 1, composition 5 comprising the ingredients shown in Table 7 was prepared, with all amounts expressed by percentages by weight of active matter with regard to the total weight of the composition.

Table 7: Composition 5

The composition obtained with the ingredients listed in Table 7 is in the form of a structured emulsion, which is within the scope of the present invention.

The degradation of ferulic acid, phenylethyl resorcinol and capryloyl salicylic acid in composition 5 after storage was tested and the results were summarized in Table 8.

Table 8

Example 4

Following the procedure in Example 1, composition 6 comprising the ingredients shown in Table 9 was prepared, with all amounts expressed by percentages by weight of active matter with regard to the total weight of the composition.

Table 9: Composition 6

The composition obtained with the ingredients listed in Table 9 is in the form of a structured emulsion, which is within the scope of the present invention.

The degradation of ferulic acid in composition 6 after storage was tested and the results were summarized in Table 10.

Table 10

	Storage condition	FA Content, %	Degradation, %
Composition 6	45C for 2 months	0.48	4

It can be clearly seen that improved stability (i.e. the degradation of ferulic acid is less than 5%) , and reduced odor formation can be realized by the composition according to the present invention.

Claims

A composition in the form of oil-in-water emulsion for caring for keratin materials comprising:

a) ferulic acid;

b) at least one polar oil;

c) at least one compound selected from saccharides and sugar alcohols;

d) at least one surfactant; and

e) at least one saturated C ₁₂-C ₂₆ fatty alcohol.
The composition according to Claim 1, wherein the composition comprises from 0.01 wt. %to 4.0 wt. %, preferably from 0.1 wt. %to 3.0 wt. %of ferulic acid, relative to the total weight of the composition.
The composition according to Claim 1 or 2, wherein the polar oil is selected from C ₁₂-C ₁₅ alcohol benzoate, diisopropyl sebacate, isopropyl lauroyl sarcosinate, dicaprylyl carbonate, 2-phenylethyl benzoate, butyloctyl salicylate, 2-octyldodecyl neopentanoate, dicaprylyl ether, dimethyl isosorbide, isocetyl stearate, isodecyl neopentanoate, isononyl isononate, isopropyl myristate, isopropyl palmitate, isostearyl behenate, myristyl myristate, octyl palmitate, tridecyl trimellitate, and castor oil.
The composition according to Claim 1 or 2, wherein the composition comprises from 1 wt. %to 50 wt. %, preferably from 2 wt. %to 20 wt. %of the polar oil, relative to the total weight of the composition.
The composition according to any one of Claims 1-4, wherein the sugar alcohol is selected from of glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, volemitol, isomalt, maltitol, lactitol, maltotriitol, maltotetraitol, polyglgycitol, and a mixture thereof.
The composition according to any of Claims 1-5, wherein the saccharide is selected from monosaccharides such as glucose, fructose, galactose, xylose, rhamnose, fucose, arabinose, ribose, sorbose, tagatose, psicose, allose, idose, and talose, and disaccharides such as mannose, sucrose, maltose, lactose, trehalose, cellobiose, chitobiose, kojibiose, nigerose, isomaltose, sophorose, laminaribiose, gentiobiose, trehalulose, turanose, maltulose, isomaltulose, gentiobiulose, mannobiose, melibiose, melibiulose, rutinose, rutinulose, xylobiose, and a mixture thereof.
The composition according to any of Claims 1-6, wherein the composition comprises from 1 wt. %to 50 wt. %, preferably from 5 wt. %to 45 wt. %of the compound selected from saccharides and sugar alcohols, relative to the total weight of the composition.
The composition according to any of Claims 1-7, wherein the surfactant is selected from amphoteric or zwitteronic surfactants, cationic surfactants, anionic surfactants, nonionic surfactants, and a mixture thereof.
The composition according to any of Claims 1-8, wherein the composition from 0.05 wt. %to 5 wt. %, preferably from 0.1 wt. %to 3.0 wt. %of the surfactant, relative to the total weight of the composition.
The composition according to any one of Claims 1-9, wherein the saturated C ₁₂-C ₂₆ fatty alcohol is selected from cetyl alcohol, stearyl alcohol, cetylstearyl alcohol, myristyl alcohol, lauryl alcohol, tridecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, arachidyl alcohol, behenyl alcohol and myricyl alcohol.
The composition according to any one of Claims 1-10, w wherein the composition comprises from 0.5 wt. %to 25 wt. %, preferably from 1 wt. %to 10 wt. %of the saturated C ₁₂-C ₂₆fatty alcohol, relative to the total weight of the composition.
The composition according to any one of Claims 1-11, wherein the composition further comprises at least one lipophilic thickener and/or hydrophilic thickener.
A composition in the form of oil-in-water emulsion for caring for keratin materials comprising, relative to the total weight of the composition:

a) from 0.1 wt. %to 3.0 wt. %of ferulic acid;

b) from 2 wt. %to 20 wt. %of at least one polar oil selected from isopropyl lauroyl sarcosinate, dimethyl isosorbice, and castor oil;

c) from 5 wt. %to 45 wt. %of at least one compound selected from glycerine, mannose, sucrose, and sorbitol;

d) from 0.1 wt. %to 3.0 wt. %of at least one surfactant; and

e) from 1 wt. %to 10 wt. %of at least one saturated C ₁₂-C ₂₆ fatty alcohol selected from cetyl alcohol, stearyl alcohol and cetylstearyl alcohol.
A process for caring for keratin materials, comprising applying the composition according to any of claims 1-13 to the keratin materials.