WO2021134458A1

WO2021134458A1 - Composition for conditioning keratin materials

Info

Publication number: WO2021134458A1
Application number: PCT/CN2019/130460
Authority: WO
Inventors: Amit Jayaswal; Cherry YANG; Shichen ZHANG
Original assignee: L'oreal
Priority date: 2019-12-31
Filing date: 2019-12-31
Publication date: 2021-07-08
Also published as: CN114828814A

Abstract

It relates to an oil-in-water (O/W) emulsion composition useful in a product for conditioning keratin materials, comprising: a fatty acid-ester mixture; and at least one cationic surfactant.

Description

Composition for conditioning keratin materials

Technical field

The present invention relates to a composition for conditioning keratin materials, in particular the hair along with scalp. The invention also relates to a process for conditioning keratin materials, in particular the hair along with scalp, using the composition of the present invention.

Background

Keratin materials are present widely on surface of human bodies, e.g., skin, scalp and hair. Many people have for a long time sought to soothing the body surface, so as to feel comfortable in daily life and work. Amongst others, the feeling of itch is particularly concerned by many people. Various factors may cause the feeling of itch, e.g., high dryness of body surface, presence of certain bacteria on body surface, allergy, external stimuli or even psychological feeling, etc. Accordingly, various products are developed to deal with the itchy feeling of person, many of which are used to soothe the feeling of itch. In particular, considering the various factors, soothing the feeling of itchy is usually more feasible and meaningful than therapeutic treatment against directly the factors.

In the keratin materials on body surface, the scalp is particularly readily to suffer from itch. Various formulations have been developed for the itchy scalp, including those provided in a separate form, e.g., lotion, spray and the like, and those incorporated into conventional products for hair and/or for scalp, e.g., shampoo, leave-on and/or rinse-off conditioner.

Keratin fibers, in particular the hair is cleansed and treated with many cosmetic regiments to improve its look, color, style, etc. These various regiments however can remove the hair’s natural oils and impart structural damage to the hair. For instance, shampooing is used primarily to cleanse the hair. Shampoos are often formulated with anionic surfactants that primarily clean as opposed to condition the hair. Anionic surfactants are highly effective for removing dirt, pollution, build-up, etc., from the hair, but they also remove sebum, a naturally occurring oily or waxy matter that automatically lubricates hair.

Conditioning compositions are used to improve or return to the hair its natural luster, shine, smoothness, and softness, for example, after shampooing the hair and/or after subjecting the hair to a chemical treatment. Conditioning compositions are often applied as rinses, cream-like emulsions, or lotions, and typically include one or more cationic compound. When used with shampooing, the commonly accepted method for conditioning the hair has been to shampoo the hair, followed by rinsing the hair, and then applying a conditioner composition, optionally followed by a second rinse. This improves the wet combing properties of the hair often because the conditioner composition coats the hair shaft and causes individual hair fibers in to resist tangling and matting because of the conditioner residue retained on the hair shaft.

On the other hand, for cosmetic uses, natural ingredients, i.e., ingredients of natural origin, are of great interest to the consumers. Many compounds with natural origin are used in formulating compositions for conditioning and/or caring forkeratin materials. Efforts have been made to formulate compositions comprising natural ingredients.

There is thus still needed in the art to develop new compositions for conditioning keratin materials to satisfy multiple demands by consumers, especially the anti-itching effect incorporated with the conventional conditioning effects.

Summary of the invention

In medical science, medium chain fatty acids and the respectively corresponding monoglycerides have been disclosed to have a broad spectrum of anti-microbial activity against enveloped viruses and various bacteria in vitro (Kabara, 1978; Shibasaki and Kato, 1978; Welsh et al. 1979 Thormar et al., 1987; Isaacs et al. 1995) , comprising but not limited to human pathogens such as herpes simplex virus, Candida albicans, Chlamydia trachomatis, Nesseria gonorrhoeae, Helicobacter pylori and Staphylococcus aureus. The inventors have now discovered that the use of a fatty acid-ester mixture of a plurality, e.g., at least 3, 4, or 5, of medium chain fatty acids and monoesters of the respective medium chain fatty acids with a lower polyol, makes it possible to obtain a composition for conditioning keratin materials, which can non-therapeutically soothe the itchy feeling occurring on the keratin materials, especially on scalp.

One subject of the present invention is thus a composition for conditioning keratin materials, comprising:

a fatty acid-ester mixture of a plurality, e.g., at least 3, 4, or 5, of medium chain fatty acids and a plurality, e.g., at least 3, 4, or 5, of monoesters; and

at least one cationic surfactant.

The composition according to the present invention is particularly useful for conditioning keratin materials, such as, in particular for hair and/or scalp care.

According to an embodiment of the invention, the fatty acid-ester mixture is a derivative of coconut oil, called as activated virgin coco oil (AVCO) .

The inventors have further surprisingly discovered that a fatty substance can benefit the composition of the invention to achieve better condition effect.

Notably, as introduced above, although medium chain fatty acids and monoglycerides thereof are known to have anti-microbial activity, various factors may cause the feeling of itch. The composition of the invention has been discovered, and also has been proved through experiments, that itchy feeling can be successfully soothed. Without being restricted to any known theory, it is believed that the successful use of the composition of the invention to soothe the itchy feeling contributes at least a part to the sensory relax to the keratin materials by the composition of the invention. Accordingly, the composition of the invention is limited to non-therapeutic uses, though it may be discovered further properties and/or mechanisms for a therapeutic use in the future.

Embodiments of the invention

Throughout the description, including the claims, the term "comprising a" should be understood as being synonymous with "comprising at least one" , unless otherwise mentioned. Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .

Throughout the description, including the claims, an embodiment defined with “comprising” or the like should be understood to encompass a preferable embodiment defined with “consisting substantially of” and a preferable embodiment defined with “consisting of” .

Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of components and/or reaction conditions are to be understood as being modified in all instances by the term "about, " meaning within 10%of the indicated number (e.g. "about 10%" means 9%-11%and "about 2%" means 1.8%-2.2%) .

Throughout the description, including the claims, the “keratin material” according to the present invention is the skin, hair, scalp, eyelashes, eyebrows, bodily hair, nails, lips or mucous membranes. Preferably, the keratin material according to the present invention is a position where an itchy feeling is easily felt, e.g., scalp, or skin, and/or a position where the itchy feeling has an impact on, e.g., hair.

Throughout the description, including the claims, the “care for” , “caring for” and the like according to the present invention should be understood to encompass any means to take care, maintain or improve the status of keratin materials, including not only the conventional means of caring for keratin materials, e.g., skin or scalp, but also any means known to be useful for conditioning and/or cleansing keratin materials, e.g., hair or scalp.

In the application, unless specifically mentioned otherwise, contents, parts and percentages are expressed on a weight basis.

The present invention is directed to a composition for conditioning keratin materials, comprising:

(A) a fatty acid-ester mixture comprising:

(A-I) . a fatty acid component comprising a plurality, e.g., at least 3, 4, or 5, of medium chain fatty acids, and

(A-II) . an ester component comprising a plurality, e.g., at least 3, 4, or 5, of monoesters of medium chain fatty acids;

wherein the medium chain fatty acid denotes a monocarboxylic acid having 6 to 20 carbon atoms; and

(B) at least one cationic surfactant.

Preferably, the monoesters of the ester component (A-II) are respectively obtained from esterification of the medium chain fatty acids used in component (A-I) with a lower polyol.

Preferably, the fatty acid-ester mixture is a derivative of coconut oil, called as activated virgin coco oil (AVCO) .

The present invention thus provides use of the fatty acid-ester mixture for soothing the feeling of itching of keratin materials on body surface, especially scalp.

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

Fatty acid-ester mixture (A)

The composition of the present invention comprises a fatty acid-ester mixture (A) of a plurality, e.g., at least 3, 4, or 5, of medium chain fatty acids and monoesters of the respective medium chain fatty acids with a lower polyol.

The useful fatty acid useful as component (A-I) according to the present invention is a medium chain fatty acid, e.g., preferably a monocarboxylic acid having 6 to 20 carbon atoms, preferably 8-16 carbon atoms, more preferably 8-12 carbon atoms. Accordingly, the useful fatty acid can have a formula (I) :

R-C (O) -OH (I)

wherein:

R represents a linear or branched, saturated or unsaturated C ₅-C ₁₉, preferably C ₇-C ₁₅, more preferably C ₇-C ₁₁, hydrocarbyl group, preferably alkyl; and preferably, R is a linear group; and more preferably, R is a linear alkyl.

According to an embodiment of the present invention, R has preferably odd number, e.g., 5, 7, 9, 11, 13, 15, 17 or 19, of carbon atoms. More preferably, R has 7, 9, 11, 13 or 15 carbon atoms; or preferably, R has 7, 9 or 11 carbon atoms.

According to an embodiment of the present invention, the medium chain fatty acid can be used alone or as a combination of two or more fatty acids. Preferably, the medium chain fatty acid is used as a combination of at least 3, 4, or 5 fatty acids.

The useful fatty acid according to the present invention can be preferably at least partially esterified with a polyol.

According to an embodiment of the present invention, the monoester useful as component (A-II) is a monoester of formula (II) :

R-C (O) -OR’ (II)

wherein:

R is as defined in formula (I) .

R’ represents a residue from a polyol. The useful polyol especially contains from 2 to 20 carbon atoms, preferably containing from 2 to 10 carbon atoms and preferably containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol.

Preferably, the fatty acid according to formula (I) includes caprylic acid (C8, also called as octoic acid) , capric acid (C10) , lauric acid (C12) , myristic acid (C14) , palmitic acid (C16) , stearic acid (C18) , or arachidic acid (C20) .

More preferably, in the formula (II) , R and R’a re different from one another, wherein R represents a linear C ₇-C ₁₅ alkyl, and R’ represents a residue from a linear polyol containing from 2 to 6 carbon atoms.

According to an embodiment of the present invention, the fatty acid according to formula (I) is preferably used in combination with the monoester according to formula (II) , so as to form the fatty acid-ester mixture (A) . Preferably, the fatty acid and the monoester for the mixture (A) involve the same fatty acid moiety, i.e., the fatty acid of formula (I) and the monoester of formula (II) having the corresponding R group. That is, if a fatty acid of formula (I) having octyl as R, i.e., being a caprylic acid, is used, then, an monoester of formula (II) having octyl as R, i.e., being an monoester of caprylic acid, is used, to form the fatty acid-ester mixture (A) . Also, if two or more fatty acids are concurrently used for the mixture (A) , then the corresponding two or more monoesters respectively having the same fatty acid moieties are used. In other words, according to an embodiment of the present invention, the fatty acid-ester mixture (A) can be deemed as a mixture of two or more fatty acids of formula (I) and the partially esterified monoesters of the each fatty acid.

According to an embodiment of the present invention, the fatty acid-ester mixture (A) comprises a plurality, e.g., at least 3, 4, or 5, of fatty acids of formula (I) and monoesters of formula (II) having the corresponding R groups respectively same as the fatty acids of formula (I) . Corresponding to the fatty acid moieties, it is preferred that a same polyol is used to form the monoesters. That is, for the two more monoesters of formula (II) for the fatty acid-ester mixture (A) , they have the same R’ group. Amongst others, glycerol is particularly used, so as to form glycerides with the variously corresponding fatty acids mentioned above.

According to an embodiment of the present invention, for example, the fatty acid-ester mixture (A) comprises at least 3 fatty acids selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and arachidic acid, to be used as component (A-I) . Meanwhile, the corresponding monoesters of the each fatty acid in component (A-I) are used as component (A-II) . Preferably, the monoesters of component (A-II) is each a glyceride.

Preferably, according to an embodiment of the present invention, the fatty acid component (A-I) comprises caprylic acid, capric acid, and lauric acid. Meanwhile, the corresponding component (A-II) comprises caprylic glyceride (also called as monocaprylin) , capric glyceride (also called as monocaprin) , and lauric glyceride (also called as monolaurin) .

According to an embodiment of the present invention, for example, regarding the fatty acid-ester mixture (A) , the total amount of fatty acids of component (A-I) and the total amount of monoesters of component (A-II) , e.g., glycerides, thereof are present in a ratio ranging from 4: 1 to 1: 1, preferably 3: 1 to 1: 1, more preferably 2.5: 1 to 1.5: 1.

According to an embodiment of the present invention, for example, the fatty acid-ester mixture (A) can be obtained by partially esterifying directly the fatty acid component (A-I) with a polyol to form monoesters, so as to obtain a mixture of fatty acids and the corresponding monoesters as ester component (A-II) . As a polyol is used, it is well understood that a multiester, e.g., diester, triester and the like, may be finally formed. Accordingly, a fatty acid-ester mixture (A) comprising at least 3 fatty acids, monoesters corresponding to the at least 3 fatty acids, and multiesters corresponding to the at least 3 medium chain fatty acids, is still useful for the purpose of the present invention, as long as the main purpose, in particular the anti-itching effect, is not significantly damaged.

For the purpose of the present invention, term “multiester” is provided to mean an ester formed from an esterification of a polyol, wherein more than one hydroxyl group of a polyol molecule is esterified. Accordingly, “diester” and “triester” according to the present invention mean respectively two and three hydroxyl groups of a polyol molecule is esterified.

For example, when glycerol is used to esterify a fatty acid component (A-I) , the useful fatty acid-ester mixture (A) may comprise at least 3 fatty acids, monoesters, diesters and triesters corresponding to the at least 3 fatty acids. For example, the useful fatty acid-ester mixture (A) may comprise caprylic acid, capric acid, and lauric acid, as component (A-I) ; monocaprylin, monocaprin, and monolaurin, as component (A-II) ; and diglyceride and triglyceride of caprylic acid, capric acid, and lauric acid.

When the fatty acid-ester mixture (A) also comprises a multiester, the content of the multiester is not particularly limited, as long as the main purpose, in particular the anti-itching effect, of the mixture (A) is not significantly damaged. For example, the multiester can be used in the mixture (A) in an amount up to 90wt%, preferably 80wt%or less, or preferably 70 wt%or less, or preferably 65 wt%or less.

AVCO

According to an embodiment of the present invention, for example, the fatty acid-ester mixture (A) can be of natural origin. Amongst others, it is quite known that coconut oil comprises a mixture of various C8-C20 fatty acids, especially those having even number of carbon atoms. Thus, it is desirable for the present invention to use a derivative of coconut oil, e.g., an esterified product of coconut oil, as the fatty acid-ester mixture (A) .

Amongst others, a useful derivative of coconut oil is the one called as activated virgin coco oil (AVCO) . Preferably, the coconut oil is esterified with glycerol. An AVCO useful according to the present invention may comprise caprylic acid, capric acid, and lauric acid, as component (A-I) ; monocaprylin, monocaprin, and monolaurin, as component (A-II) .

According to an embodiment of the present invention, for example, as a useful AVCO, the total amount of fatty acids of component (A-I) and the total amount of mono-glycerides of component (A-II) , are present in a ratio ranging from 4: 1 to 1: 1, preferably 3: 1 to 1: 1, more preferably 2.5: 1 to 1.5: 1. More specifically, for example, in exemplary embodiment 1 for AVCO, a useful AVCO may comprise: fatty acid component (A-I) : caprylic acid in an amount of 5-20 wt%, preferably 7-15 wt%, or preferably 8-10 wt%; capric acid in an amount of 1-10 wt%, preferably 2-8 wt%, or preferably 4-7 wt%; and lauric acid in an amount of 20-70 wt%, preferably 30-60 wt%, or preferably 40-55 wt%; and monoester component (A-II) : monocaprylin in an amount of 0.5-15 wt%, preferably 1-10 wt%, or preferably 4-7 wt%; monocaprin in an amount of 0.1-10 wt%, preferably 1-8 wt%, or preferably 3-5 wt%; and monolaurin in an amount of 10-40 wt%, preferably 15-35 wt%, or preferably 20-30 wt%; each relative to the total amount of the fatty acid component (A-I) and the monoester component (A-II) .

An AVCO obtained from the esterification of coconut oil can further comprise diglyceride and triglyceride in addition to the fatty acid component (A-I) and the monoester component (A-II) above. According to an embodiment of the present invention, for example, a useful AVCO may comprise caprylic acid, capric acid, and lauric acid, as component (A-I) ; monocaprylin, monocaprin, and monolaurin, as component (A-II) ; and optionally diglyceride and triglyceride of caprylic acid, capric acid, and lauric acid.

When the AVCO also comprises a multiester selected from diglyceride and triglyceride, the content of the multiester is not particularly limited, e.g., in an amount up to 90wt%, preferably 80wt%or less, or preferably 70 wt%or less, or preferably 65 wt%or less.

According to an embodiment of the present invention, for example, a useful AVCO may comprise: a fatty acid component (A-I) comprising caprylic acid, capric acid, and lauric acid, in an amount of 5-40 wt%, preferably 10-30 wt%, or preferably 20-25 wt%; a monoester component (A-II) comprising monocaprylin, monocaprin, and monolaurin, in an amount of 1-30 wt%, preferably 5-20 wt%, or preferably 10-15 wt%; diglycerides of caprylic acid, capric acid, and lauric acid, in a sum amount of 10-50 wt%, preferably 20-45 wt%, or preferably 30-40 wt%; and triglycerides of caprylic acid, capric acid, and lauric acid, in a sum amount of 10-70 wt%, preferably 15-50 wt%, or preferably 20-30 wt%; each relative to the total amount of the AVCO.

A useful AVCO can be preferably one prepared according to the teaching by EP 1973415, which disclosure is incorporated herein by reference. Accordingly, an exemplary AVCO can comprise: 24.63 mg/g caprylic acid (C8) , 17.81 mg/g capric acid (C10) , 133.70 mg/g lauric acid (C12) and 11.82 mg/g monocaprylin, 8.29 mg/g monocaprin and 57.16 mg/g monolaurin; or 23.10 mg/g caprylic acid (C8) , 16.08 mg/g capric acid (C10) , 116.81 mg/g lauric acid (C12) and 16.04 mg/g monocaprylin, 10.35 mg/g monocaprin and 75.54 mg/g monolaurin; each relative to the total weight of the AVCO; and preferably, the AVCO is derived from catalyzing coconut oil with 1, 3-specific lipase and subjecting it to glycerolysis.

The fatty acid-ester mixture (A) may be present in the composition according to the present invention in an amount ranging from 0.01%to 10%by weight, preferably ranging from 0.1%to 5%by weight, or preferably ranging from 0.5%to 3%by weight, or preferably ranging from 0.8%to 1.5%by weight, relative to the total weight of the composition.

Cationic surfactant (B)

According to an embodiment of the invention, the composition of the present invention may comprise at least one cationic surfactant useful as component (B) . Mention may be made, for example, of optionally polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.

Examples of quaternary ammonium salts that may especially be mentioned include:

- a) those corresponding to the general formula (V) below:

in which formula (V) the groups R ₈ to R ₁₁, which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms or an aromatic group such as aryl or alkylaryl, at least one of the groups R ₈ to R ₁₁ comprising from 8 to 30 carbon atoms and preferably from 12 to 24 carbon atoms. The aliphatic groups may comprise heteroatoms such as, in particular, oxygen, nitrogen, sulfur and halogens.

The aliphatic groups are chosen, for example, from C ₁-C ₃₀ alkyl, C ₁-C ₃₀ alkoxy, polyoxy (C ₂-C ₆) alkylene, C ₁-C ₃₀ alkylamide, (C ₁₂-C ₂₂) alkylamido (C ₂-C ₆) alkyl, (C ₁₂-C ₂₂) alkylacetate, C ₁-C ₃₀ hydroxyalkyl, X ^-is an anionic counterion chosen from halides, phosphates, acetates, lactates, (C ₁-C ₄) alkyl sulfates, and (C ₁-C ₄) alkyl-or (C ₁-C ₄) alkylarylsulfonates, preferably halides, e.g., fluoride, chloride, bromide or the like.

Among the quaternary ammonium salts of formula (V) , preference is given firstly to tetraalkylammonium halides such as tetraalkylammonium chlorides, for instance tetraalkylammonium or alkyltrimethylammonium halides such as dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group contains from approximately 12 to 22 carbon atoms, in particular halides such as behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, benzyldimethylstearylammonium chloride, or else, secondly, alkoxy sulfates, especially distearoylethylhydroxyethylmethylammonium methosulfate, dipalmitoylethylhydroxyethylammonium methosulfate or distearoylethylhydroxyethylammonium methosulfate, or else, lastly, palmitylamidopropyltrimethylammonium halide, particularly the chloride or stearamidopropyldimethyl (myristyl acetate) ammonium chloride, sold under the name

70 by the company Van Dyk;

-b) quaternary ammonium salts of imidazoline, for instance those of formula (VI) below:

in which formula (VI) :

R ₁₂ represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow;

R ₁₃ represents a hydrogen atom, a C ₁-C ₄ alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms;

R ₁₄ represents a C ₁-C ₄ alkyl group;

R ₁₅ represents a hydrogen atom or a C ₁-C ₄ alkyl group;

X ^-represents an anionic counterion chosen in particular from halides, phosphates, acetates, lactates, (C ₁-C ₄) alkyl sulfates, (C ₁-C ₄) alkyl-or (C ₁-C ₄) alkylarylsulfonates.

R ₁₂ and R ₁₃ preferably denote a mixture of alkyl or alkenyl groups containing from 12 to 21 carbon atoms, derived for example from tallow fatty acids, R ₁₄ preferably denotes a methyl group, and R ₁₅ preferably denotes a hydrogen atom. Such a product is sold, for example, under the name

W 75 by the company Rewo;

- c) quaternary diammonium or triammonium salts, particularly of formula (VII) below:

in which formula (VII) :

R ₁₆ denotes an alkyl group comprising from about 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted with one or more oxygen atoms;

R ₁₇ is chosen from hydrogen, an alkyl group comprising from 1 to 4 carbon atoms or a group- (CH ₂) ₃-N ⁺ (R _16a) (R _17a) (R _18a) ; R _16a, R _17a, R _18a, R ₁₈, R ₁₉, R ₂₀ and R ₂₁, which may be identical or different, are chosen from hydrogen and an alkyl group comprising from 1 to 4 carbon atoms, and

X ^-represents an anionic counterion chosen in particular from halides, acetates, phosphates, nitrates, (C ₁-C ₄) alkyl sulfates, (C ₁-C ₄) alkyl-or (C ₁-C ₄) alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate. Such compounds are, for example, Finquat CT-P, available from the company Finetex (Quaternium 89) , and Finquat CT, available from the company Finetex (Quaternium 75) ;

-d) quaternary ammonium salts containing one or more ester functions, such as those of formula (VIII) below:

in which formula (VIII) :

■ R ₂₂ is chosen from C ₁-C ₆ alkyl and C ₁-C ₆ hydroxyalkyl or dihydroxyalkyl groups;

■ R ₂₃ is chosen from:

- the group

- linear or branched, saturated or unsaturated C ₁-C ₂₂ hydrocarbon-based groups R ₂₇,

- a hydrogen atom;

■ R ₂₅ is chosen from:

- the group

- linear or branched, saturated or unsaturated C ₁-C ₆ hydrocarbon-based groups R ₂₉,

- a hydrogen atom;

■ R ₂₄, R ₂₆ and R ₂₈, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C ₇-C ₂₁ hydrocarbon-based groups;

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

■ r1 and t1, which may be identical or different, are equal to 0 or 1, with r2+r1=2r and t1+t2=2t,

■ y is an integer ranging from 1 to 10;

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

■ X ^-represents an organic or inorganic anionic counterion;

with the proviso that the sum x+y+z is from 1 to 15, that when x is 0, then R ₂₃ denotes R ₂₇ and that when z is 0, then R ₂₅ denotes R ₂₉.

The alkyl groups R ₂₂ may be linear or branched, and more particularly linear.

Preferably, R ₂₂ denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.

Advantageously, the sum x+y+z is from 1 to 10.

When R ₂₃ is a hydrocarbon-based group R ₂₇, it may be long and may contain from 12 to 22 carbon atoms, or may be short and may contain from 1 to 3 carbon atoms.

When R ₂₅ is a hydrocarbon-based group R ₂₉, it preferably contains 1 to 3 carbon atoms.

Advantageously, R ₂₄, R ₂₆ and R ₂₈, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C ₁₁-C ₂₁ hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C ₁₁-C ₂₁ alkyl and alkenyl groups.

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

Advantageously, y is equal to 1.

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

The anionic counterion X ^-is preferably a halide, preferably such as chloride, bromide or iodide, a (C ₁-C ₄) alkyl sulfate or a (C ₁-C ₄) alkyl-or (C ₁-C ₄) alkylaryl-sulfonate. However, use may be made of methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate or lactate, or any other anion compatible with the ammonium containing an ester function.

The anionic counterion X ^-is even more particularly chloride, methyl sulfate or ethyl sulfate.

Use is made more particularly, in the composition according to the invention, of the ammonium salts of formula (VIII) in which:

- R ₂₂ denotes a methyl or ethyl group,

- x and y are equal to 1,

- z is equal to 0 or 1,

- r, s and t are equal to 2,

- R ₂₃ is chosen from:

● the group

● methyl, ethyl or C14-C22 hydrocarbon-based groups,

● a hydrogen atom,

- R ₂₅ is chosen from:

● the group

● a hydrogen atom,

- R ₂₄, R ₂₆ and R ₂₈, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C ₁₃-C ₁₇ hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C ₁₃-C ₁₇ alkyl and alkenyl groups.

Advantageously, the hydrocarbon-based radicals are linear.

Among the quaternary ammonium salts containing one or more ester functions of formula (VIII) , examples that may be mentioned include salts, especially the chloride or methyl sulfate, of diacyloxyethyldimethylammonium, diacyloxyethylhydroxy-ethylmethylammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyloxy-ethylmethylammonium or monoacyloxyethylhydroxyethyldimethylammonium, and mixtures thereof. The acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a plant oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.

These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, an alkyldiethanolamine or an alkyldiisopropanolamine, which are optionally oxyalkylenated, with fatty acids or with fatty acid mixtures of plant or animal origin, or by transesterification of the methyl esters thereof. This esterification is followed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.

Such compounds are sold, for example, under the names

by the company Henkel,

by the company Stepan,

by the company Ceca or

WE 18 by the company Rewo-Witco.

The composition according to the invention may contain, for example, a mixture of quaternary ammonium salts of mono-, di-and triesters with a weight majority of diester salts.

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

Use may be made of behenoylhydroxypropyltrimethylammonium chloride sold by KAO under the name Quatarmin BTC 131.

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

Some amines may provide cations when being interacted with other reagents, e.g., certain acids. In such cases, the specific amines may be classified into the useful cationic surfactant.

Preferred examples of the useful cationic surfactant comprise non-silicone cationic surfactants, including cetyl triammonium, behenyl triammonium, dipalmitoylethyl hydroxyethyl methyl ammonium, distearoylethyl hydroxyethyl methyl ammonium, methyl (C9-C19) alkyl, (C10-C20) alkyl amidoethylimidazolium, and stearamidopropyldimethylamine, a salt of stearamidopropyl dimethylammonium, and mixtures thereof.

According to a preferred embodiment, the cationic surfactant is the chloride and bromide salts of tetraalkylammonium, alkylamidoalkyltrialkylammonium, trialkylbenzylammonium, trialkylhydroxyalkylammonium or alkylpyridinium.

According to an embodiment, among the cationic surfactants that may be present in the composition according to the invention, it is more particularly preferred to choose stearamidopropyldimethyl (myristyl acetate) ammonium chloride, cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxyethylmethylammonium salts, and mixtures thereof, and more particularly stearamidopropyldimethyl (myristyl acetate) ammonium chloride, behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and dipalmitoylethylhydroxyethylammonium methosulfate, and mixtures thereof.

Advantageously, the content of at least one cationic surfactant represents from 0.001%to 10%by weight, preferably from 0.005%to 5%by weight, more preferably from 0.01%to 3%by weight, relative to the weight of the composition.

Additional oils

The composition according to the present invention may optionally comprise additional oils, in addition to the fatty acids and esters thereof used in the fatty acid-ester mixture (A) , conventionally used for cosmetic use.

The additional oils may be volatile or non-volatile.

The term "volatile oil" refers to any non-aqueous medium capable of evaporating from the skin or lips, in less than one hour, at room temperature (20-25℃) and atmospheric pressure (760 mmHg) .

More specifically, the volatile oil may be a volatile cosmetic oil, liquid at room temperature. More specifically, a volatile oil has an evaporation rate of between 0.01 and 200mg/cm ²/min, inclusive.

The term "non-volatile oil" is intended to mean an oil remaining on the skin or keratin fiber at ambient temperature and atmospheric pressure. More specifically, anon-volatile oil has an evaporation rate strictly below 0.01 mg/cm ²/min.

The additional oils may accordingly be liquid or solid at room temperature.

The additional oils that are suitable for the present invention may be hydrocarbon-based, silicone-based or fluorine-based. According to a preferred embodiment of the present invention, the composition is free of silicone-based oil.

According to the present invention, the term "silicone oil" refers to an oil including at least one silicon atom, and in particular at least on Si-O group.

The term "fluorine oil" refers to an oil including at least one fluorine atom.

The term "hydrocarbon-based oil" refers to an oil containing primarily hydrogen and carbon atoms.

The oils may optionally include oxygen, nitrogen, sulfur and/or phosphorus atoms, for example, in the form of hydroxyl or acid radicals.

More preferably, the composition of the present invention comprises hydrocarbon oil (s) .

Specifically, the volatile oils may be chosen from hydrocarbon oils having 8 to 16 carbon atoms, and in particular branched C ₈-C ₁₆ alkanes (also called isoparaffins or isoalkanes) , such as isododecane (also called 2, 2, 4, 4, 6-pentamethylheptane) , isodecane, isohexadecane, and, for example, the oils sold under the trade names

or

It is also possible to cite, as a hydrocarbon volatile oil, linear C ₉-C ₁₇ alkanes, such as dodecane (C ₁₂) and tetradecane (C ₁₄) , sold respectively under the names

12-97 and

14-97 (Sasol) , and, as alkanes obtained according to the method described in the international application WO 2007/068371 A1, such as the undecane (C ₁₁) and tridecane (C ₁₃) mixture sold under the name

The non-volatile oils may, in particular, be chosen from among the non-volatile hydrocarbon oils.

According to a preferred embodiment, the composition of the present invention comprises at least one oil selected from the group consisting of plant oil, fatty alcohols, or a mixture thereof.

In particular, the term "plant oil" means an oil as defined above, obtained from a species belonging to the plant kingdom.

As examples of plant oils that are suitable for the present invention, mentions maybe made of:

- sweet almond oil,

- argan oil,

- avocado oil,

- peanut oil,

- camellia oil,

- safflower oil,

- calophyllum oil,

- coconut oil,

- colza oil,

- copra oil,

- coriander oil,

- cucurbit oil,

- wheatgerm oil,

- jojoba oil or jojoba liquid wax,

- linseed oil,

- macadamia oil,

- maize germ oil,

- hazelnut oil,

- walnut oil,

- vernonia oil,

- apricot kernel oil,

- olive oil,

- evening primrose oil,

- palm oil,

- passionflower oil,

- grapeseed oil,

- rose oil,

- castor oil,

- rye oil,

- sesame oil,

- rice bran oil,

- soya oil, or soybean oil, and

- sunflower oil.

Preferably, the composition of the present invention may further comprise at least one plant oil selected from apricot kernel oil, soya oil, or a mixture thereof.

Examples of fatty alcohols that can be used in the composition of the present invention include C8-C22 alcohol, preferably C16-C18 alcohol, e.g., capryl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, or a mixture thereof.

The amount of additional oil (s) , when they are present in the composition, preferably ranges from 0.01%to 20%by weight, better still from 0.05%to 10%by weight and more particularly from 0.1%to 5%by weight relative to the total weight of the final composition.

Solvent

The composition according to the invention can advantageously comprise one or more solvent, e.g., water and/or organic solvent, in the aqueous phase.

Water

The composition according to the invention may advantageously comprises water in a content of 40%by weight relative to the total weight of composition. The water content in the low viscosity composition according to the invention preferably ranges from 40%to 90%by weight, more preferably from 50%to 90%by weight, or from 60%to 85%by weight, relative to the total weight of the composition.

Organic solvent

The composition according to the invention may also comprise one or more organic solvents, preferably water-soluble organic solvents (solubility of greater than or equal to 5%in water at 25℃and at atmospheric pressure) .

Examples of the organic solvents that may be mentioned include linear or branched, and preferably saturated, monoalcohols or diols, comprising 2 to 10 carbon atoms, such as ethyl alcohol, isopropyl alcohol, hexylene glycol (2-methyl-2, 4-pentanediol) , neopentyl glycol and 3-methyl-1, 5-pentanediol, butylene glycol, dipropylene glycol and propylene glycol; aromatic alcohols such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycerol; polyol ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether; and also diethylene glycol alkyl ethers, especially C ₁-C ₄ alkyl ethers, for instance diethylene glycol monoethyl ether or monobutyl ether, alone or as a mixture.

The organic solvents, when they are present, generally represent between 0.1%and 20%by weight relative to the total weight of the composition according to the invention, and preferably between 0.2%and 10%by weight, or between 0.3%and 5%by weight.

Additional Additives

According to various embodiments, the compositions of the present invention are provided for application to keratin materials, such as skin, scalp or hair. In accordance with these embodiments, the compositions of the present invention can comprise various ingredients conventionally useful in compositions for conditioning keratin materials, such as,additional surfactant including nonionic surfactant, anionic surfactant and amphoteric surfactant, active ingredients, humectants, additional fatty substances, antidandruff agents, anti-seborrhoea agents, agents for preventing hair loss and/or for promoting hair regrowth, vitamins and provitamins including panthenol, sunscreens, sequestrants, plasticizers, acidifying agents, opacifiers, pearlescent or nacreous agents, antioxidants, hydroxyacids, fragrances and preserving agents.

A non-exhaustive listing of such ingredients can be found in U.S. patent application publication no. 2004/0170586, the entire contents of which is hereby incorporated by reference. Still further examples of such additional ingredients may be found in the International Cosmetic Ingredient Dictionary and Handbook (9 ^th ed. 2002) .

A person skilled in the art will take care to select the optional additional additives and/or the amount thereof such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.

These additives may be selected variously by the person skilled in the art in order to prepare a composition which has the desired properties, for example, consistency or texture. In particular, the additives, if used, and the amounts thereof are particularly determined according to the specific products/applications thereof, e.g., leave-on conditioner, rinse-off conditioner, skincare conditioner and the like.

These additives may be present in the composition in an amount from 0.01%to 50%relative to the total weight of the composition, including all ranges and subranges therebetween.

Method and use

The composition according to the present invention can be generally prepared according to the general knowledge of a person skilled in the art. Nevertheless, it is to be understood that a person skilled in the art can choose the method of preparation, on the basis of his/her general knowledge, taking into account the nature of the constituents used, for example, their solubility in the vehicle, and the application envisaged for the compositions or the kit.

According to an embodiment, the composition according to the present invention can be used for caring for keratin materials, especially the skin, scalp and/or hair. This use may manifest itself as a process for caring for keratin materials, especially the skin, scalp and/or hair, comprising the step applying to said keratin materials the composition of the invention.

The composition according to the present invention is preferably useful to formulate hair conditioner products, scalp care products, or even skincare products. Also, according to the detailed discussions above, it is to be understood that composition, and in turn the shampoo product according to the present invention may be free of silicone oil.

The keratin fibers conditioning composition of the present invention can be used in the form of rinse-off products or leave-on products, and can be formulated in a wide variety of product forms, including but not limited to creams, gels, emulsions, mousses and sprays. The composition of the present invention is especially suitable for after-shampoo conditioner.

The keratin fibers conditioning composition as described above may be used to condition the keratin fibers such as hair through conventional methods, depending on the application form of the composition.

For example, when used as an after-shampoo conditioner, the composition of the present invention may be applied through a method comprising following steps:

(i) after shampooing hair, applying to the hair an effective amount of the conditioning composition for conditioning the hair; and

(ii) rinsing the hair.

The invention will be further illustrated by the following examples, which set forth particularly advantageous embodiments.

Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the present invention are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contain certain errors necessarily resulting from the standard deviation found in their respective measurements. The following examples are intended to illustrate the present invention without limiting the scope as a result.

Examples

The ingredient amounts/concentrations in the compositions/formulas described below were expressed in %by weight, relative to the total weight of each composition/formula.

Material:

COCOS NUCIFERA (COCONUT) OIL: activated virgin coconut oil (AVCO) , available from BIOTROPICS

Other materials without specification here were each commercially available.

Example 1

Composition A, and comparative composition C, as Table 1, were prepared:

Table 1

The above listed compositions A and C were prepared according to known manufacturing method of field.

Example 2

The soothing feeling of the composition A was evaluated. 5 volunteers between age of 25 and 45 applied the composition A on the hair and scalp every day for 3 weeks, followed by 2 weeks without using the composition A. The anti-itchy feeling (soothing feeling) was assessed in the total 5 weeks. Scores of itchy feeling before the application of the composition A was given as a baseline, the scores of itchy feeling after application of the composition A was given every day, the mean difference was shown in Table 2.

Scores were given and calculated as follows:

In the first 3 weeks, each volunteer washed hair with the composition A at every evening, in which the conventional usage of each volunteer was used. In the next 2 weeks, each volunteer washed hair with a standard shampoo without AVCO also at every evening, in which the conventional usage of each volunteer was still used.

Volunteers gave scores to the itching feeling, where:

0 meant unchanged;

-1 meant fairly improved;

-2 meant significantly improved; and

-3 meant substantially free of itching feeling.

The average scores of the 5 volunteers were counted every day, and were calculated for the averages for every week. The average scores for the total 5 weeks were provided in Table 2 below.

Table 2

	Week1	Week2	Week3	Week4	Week5
Composition A	-0.8	-1.1	-1.6	-1.4	-1.2

Referring to Table 2, less the score, less the itchy feeling was. It was observed that the composition A showed a very good and long term anti-itchy feeling, even 2 weeks after the last application of the composition.

Claims

A composition for conditioning keratin materials, comprising:

an oil phase comprising

(A) a fatty acid-ester mixture comprising:

(A-I) . a fatty acid component comprising a plurality, e.g., at least 3, 4, or 5, of medium chain fatty acids, and

(A-II) . an ester component comprising a plurality, e.g., at least 3, 4, or 5, of monoesters of medium chain fatty acids;

wherein the medium chain fatty acid denotes a monocarboxylic acid having 6 to 20 carbon atoms; and

(B) at least one cationic surfactant.
The composition according to claim 1, wherein the fatty acid-ester mixture (A) comprises at least 3 fatty acids selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and arachidic acid, to be used as component (A-I) ; and the corresponding glycerides of the each fatty acid in component (A-I) are used as component (A-II) ;

and preferably, the fatty acid component (A-I) comprises caprylic acid, capric acid, and lauric acid; while the corresponding component (A-II) comprises monocaprylin, monocaprin, and monolaurin; and

wherein the total amount of fatty acids of component (A-I) and the total amount of monoesters of component (A-II) are present in a ratio ranging from 4: 1 to 1: 1, preferably 3: 1 to 1: 1, more preferably 2.5: 1 to 1.5: 1.
The composition according to claim 1 or 2, wherein the fatty acid-ester mixture (A) is activated virgin coco oil comprising:

- fatty acid component (A-I) :

caprylic acid in an amount of 5-20 wt%, preferably 7-15 wt%, or preferably 8-10 wt%;

capric acid in an amount of 1-10 wt%, preferably 2-8 wt%, or preferably 4-7 wt%; and

lauric acid in an amount of 20-70 wt%, preferably 30-60 wt%, or preferably 40-55 wt%;

and

- monoester component (A-II) :

monocaprylin in an amount of 0.5-15 wt%, preferably 1-10 wt%, or preferably 4-7 wt%;

monocaprin in an amount of 0.1-10 wt%, preferably 1-8 wt%, or preferably 3-5 wt%; and

monolaurin in an amount of 10-40 wt%, preferably 15-35 wt%, or preferably 20-30 wt%;

each relative to the total amount of the fatty acid component (A-I) and the monoester component (A-II) .
The composition according to claim 3, wherein the activated virgin coco oil comprises:

- a fatty acid component (A-I) comprising caprylic acid, capric acid, and lauric acid, in an amount of 5-40 wt%, preferably 10-30 wt%, or preferably 20-25 wt%;

- a monoester component (A-II) comprising monocaprylin, monocaprin, and monolaurin, in an amount of 1-30 wt%, preferably 5-20 wt%, or preferably 10-15 wt%;

- diglycerides of caprylic acid, capric acid, and lauric acid, in a sum amount of 10-50 wt%, preferably 20-45 wt%, or preferably 30-40 wt%; and

- triglycerides of caprylic acid, capric acid, and lauric acid, in a sum amount of 10-70 wt%, preferably 15-50 wt%, or preferably 20-30 wt%;

each relative to the total amount of the activated virgin coco oil.
The composition according to any one of the preceding claims, wherein the fatty acid-ester mixture (A) is present in an amount ranging from 0.01%to 10%by weight, preferably ranging from 0.1%to 5%by weight, or preferably ranging from 0.5%to 3%by weight, or preferably ranging from 0.8%to 1.5%by weight, relative to the total weight of the composition.
The composition according to any one of the preceding claims, wherein the at least one cationic surfactant (B) is selected from the group consisting of optionally polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof, preferably from the group consisting of stearamidopropyldimethyl (myristyl acetate) ammonium chloride, cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxyethylmethylammonium salts, and mixtures thereof.
The composition according to any one of the preceding claims, wherein the cationic surfactant (B) is present in the composition in an amount from 0.001%to 10%by weight, preferably from 0.005%to 5%by weight, more preferably from 0.01%to 3%by weight, relative to the weight of the composition, including all ranges and subranges therebetween.
The composition according to any one of the preceding claims, further comprising at least one additional oil, selected from the group consisting of C8-C22 alcohols, preferably C16-C18 alcohols, e.g., capryl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, or a mixture thereof..
The composition according to any one of the preceding claims, wherein the at least one additional oil is present in the composition in an amount from 0.01%to 20%by weight, better still from 0.05%to 10%by weight and more particularly from 0.1%to 5%, relative to the total weight of the composition including all ranges and subranges therebetween.
The composition according to any one of the preceding claims, being free of silicone-based oil.
A hair conditioner product comprising the composition according to any one of the preceding claims 1-10.
The scalp care product according to claim 12, being a leave-on hair conditioner product or a rinse-off hair conditioner product.
A scalp care product comprising the composition according to any one of the preceding claims 1-10.
A skincare product comprising the composition according to any one of the preceding claims 1-10.