CN114828814A

CN114828814A - Composition for conditioning keratin materials

Info

Publication number: CN114828814A
Application number: CN201980103396.3A
Authority: CN
Inventors: A·贾亚斯瓦尔; C·杨; 章诗辰
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2019-12-31
Filing date: 2019-12-31
Publication date: 2022-07-29
Also published as: WO2021134458A1

Abstract

The present invention relates to an oil-in-water (O/W) emulsion composition useful in a keratin material conditioning product 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 together with the scalp. The invention also relates to a method for conditioning keratin materials, in particular the hair with the scalp, using the composition according to the invention.

Background

Keratin materials are widely found on human surfaces, such as skin, scalp and hair. Many people have long sought to soothe the body surface so that they feel comfortable in everyday life and work. Among these, many people are particularly concerned with the perception of itching. Various factors may cause itching, such as high dryness of the body surface, the presence of certain bacteria on the body surface, allergies, external irritations or even psychological sensations, etc. Accordingly, in order to solve the human itching feeling, various products have been developed, many of which are used to relieve the itching feeling. In particular, taking into account various factors, relieving itching sensation is generally more feasible and meaningful than therapeutic treatment directed against these factors.

Among keratin materials on the body surface, the scalp is particularly susceptible to itching. Various formulations have been developed for itchy scalp, including those provided in separate forms, such as lotions (lotions), sprays, and the like, as well as those incorporated into conventional products for the hair and/or scalp, such as shampoos, leave-on and/or rinse-off conditioners.

Keratin fibers, especially hair, are cleaned and treated with a number of cosmetic systems to improve their appearance, color, styling, and the like. However, these various systems can remove the natural oils from the hair and cause structural damage to the hair. For example, shampoos are used primarily to clean hair. Shampoos are typically formulated with anionic surfactants, which primarily cleanse the hair rather than condition the hair. Anionic surfactants are very effective in removing dirt, stains, accumulations, etc. from hair, but they also remove sebum, a naturally occurring oily or waxy substance that lubricates hair automatically.

Conditioning compositions are used to improve or restore the natural shine, smoothness and softness of hair, for example after shampooing and/or after applying a chemical treatment to the hair. Conditioning compositions are typically applied as rinses (rinses), cream-like lotions, or essences (lotiones), and typically include one or more cationic compounds. When used with a shampoo, a generally accepted method of conditioning hair is to shampoo the hair, then rinse the hair, then apply the conditioner composition, optionally followed by a second rinse. This improves the wet combing properties of the hair, typically by coating the hair shaft with the conditioner composition and by causing individual hair fibers to resist tangling and dulling due to the remaining conditioner residues on the hair shaft.

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

There is therefore still a need in the art to develop new compositions for conditioning keratin materials to meet the various needs of the consumer, in particular an anti-itching effect combined with a conventional conditioning effect.

Summary of The Invention

In medical science, it has been disclosed that medium-chain fatty acids and the respective corresponding monoglycerides have broad-spectrum antimicrobial activity in vitro against enveloped viruses and various bacteria (Kabara, 1978; Shibasaki and Kato, 1978; Welsh et al 1979; Thormar et al 1987; Isaacs et al 1995), including but not limited to human pathogens such as herpes simplex virus, Candida albicans, Chlamydia trachomatis, Neisseria gonorrhoeae, helicobacter pylori and Staphylococcus aureus. The inventors have now found that the use of fatty acid-ester mixtures of a plurality, for example at least 3, 4 or 5, of medium-chain fatty acids and of monoesters of the respective medium-chain fatty acids with lower polyols, makes it possible to obtain compositions for conditioning keratin materials which can non-therapeutically relieve the itching sensation appearing on the keratin materials, in particular on the scalp.

A subject of the present invention is therefore a composition for conditioning keratin materials, comprising:

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

at least one cationic surfactant.

The compositions according to the invention are particularly useful for conditioning keratin materials, for example in particular for hair and/or scalp care.

According to one embodiment of the invention, the fatty acid-ester mixture is a derivative of coconut oil known as Activated Virgin Coconut Oil (AVCO).

The inventors have further surprisingly found that fatty substances may benefit the composition of the invention to achieve a better conditioning effect.

It is noteworthy that, as introduced above, although medium-chain fatty acids and their monoglycerides are known to have antimicrobial activity, various factors can cause itching sensation. The compositions of the present invention have been found and have also been experimentally demonstrated to successfully alleviate itching. Without being bound by any known theory, it is believed that successful delivery of a scratchy sensation using the compositions of the invention contributes, at least in part, to the sensory relaxation of the keratin materials by the compositions of the invention. Thus, the compositions of the present invention are limited to non-therapeutic use, although further properties and/or mechanisms for therapeutic use may be discovered in the future.

Embodiments of the invention

Throughout the specification, including the claims, the terms "comprising a" and "an" should be understood as being synonymous with "comprising at least one" unless otherwise noted. Further, the expression "at least one" used in the present specification is equivalent to the expression "one or more".

Throughout the specification, including the claims, embodiments defined by "comprising" and the like should be understood to encompass preferred embodiments defined by "consisting essentially of …" and preferred embodiments defined by "consisting of …".

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

Throughout the description, including the claims, a "keratin material" is according to the invention skin, hair, scalp, eyelashes, eyebrows, body hair, nails, lips or mucous membranes. Preferably, the keratin material is according to the invention easily perceived to be a itching feeling site, such as the scalp or skin, and/or affected by a itching feeling site, such as the hair.

Throughout the description, including the claims, "treating" and the like, are to be understood according to the invention as including any means of maintaining, maintaining or improving the condition of keratin materials, including not only conventional means of treating keratin materials such as the skin or scalp, but also any means known to be useful for conditioning and/or cleansing keratin materials such as the hair or scalp.

In this application, unless explicitly stated otherwise, amounts, parts and percentages are by weight.

The present invention relates 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, medium chain fatty acids, and

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

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

(B) at least one cationic surfactant.

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

Preferably, the fatty acid-ester mixture is a derivative of coconut oil known as Activated Virgin Coconut Oil (AVCO).

The present invention therefore provides the use of a fatty acid-ester mixture for soothing itching sensations of keratin materials on the body surface, in particular the scalp.

Other features and advantages of the present invention will become more apparent upon reading the following specification and examples.

Fatty acid-ester mixture (A)

The compositions of the invention comprise fatty acid-ester mixtures (a) of a plurality, for example at least 3, 4 or 5, of medium-chain fatty acids and of monoesters of the respective medium-chain fatty acids with lower polyols.

Useful fatty acids which can be used as component (A-I) according to the invention are medium-chain fatty acids, for example monocarboxylic acids preferably having from 6 to 20 carbon atoms, preferably from 8 to 16 carbon atoms, more preferably from 8 to 12 carbon atoms. Accordingly, useful fatty acids may have 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, preferably alkyl; preferably, R is a linear group; more preferably, R is a straight chain alkyl group.

According to one embodiment of the invention, R preferably has an odd number, for example 5, 7, 9, 11, 13, 15, 17 or 19 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 one embodiment of the present invention, the medium-chain fatty acids may be used alone or as a combination of two or more fatty acids. Preferably, medium chain fatty acids are used as a combination of at least 3, 4 or 5 fatty acids.

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

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

R-C(O)-OR’ (II)

wherein:

r is as defined for formula (I).

R' represents a residue from a polyol. Useful polyols contain in particular from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, preferably 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) comprises caprylic acid (C8, also known as caprylic acid), capric acid (C10), lauric acid (C12), myristic acid (C14), palmitic acid (C16), stearic acid (C18) or arachidic acid (C20).

More preferably, in formula (II), R and R' are different from each other, whereinR represents a straight chain C ₇ -C ₁₅ Alkyl, and R' represents a residue from a linear polyol containing 2 to 6 carbon atoms.

According to one embodiment of the present invention, the fatty acid according to formula (I) is preferably used in combination with the monoester according to formula (II) to form the fatty acid-ester mixture (a). Preferably, the fatty acids and monoesters used in mixture (a) relate to the same fatty acid moiety, i.e. the fatty acid of formula (I) and monoester of formula (II) have corresponding R groups. That is, if the fatty acid of formula (I) having octyl as R, i.e. caprylic acid, is used, the monoester of formula (II) having octyl as R, i.e. caprylic acid monoester, is used to form fatty acid-ester mixture (a). Furthermore, if two or more fatty acids are used simultaneously in mixture (a), the corresponding two or more monoesters, each having the same fatty acid moiety, are used. In other words, according to one embodiment of the present invention, the fatty acid-ester mixture (a) may be regarded as a mixture of two or more fatty acids of formula (I) and a partially esterified monoester of each fatty acid.

According to one embodiment of the invention, the fatty acid-ester mixture (a) comprises a plurality, for example at least 3, 4 or 5, of fatty acids of formula (I) and monoesters of formula (II) having the same respective R groups as the fatty acids of formula (I), respectively. The monoester formation is preferably carried out using the same polyol, corresponding to the fatty acid moiety. That is, for two or more monoesters of formula (II) used in the fatty acid-ester mixture (a), they have the same R' group. Among these, glycerin is particularly used to form glycerides with the various corresponding fatty acids mentioned above.

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

Preferably, according to one embodiment of the present invention, the fatty acid component (a-I) comprises caprylic acid, capric acid and lauric acid. Meanwhile, the corresponding components (a-II) comprise glyceryl caprylate (also known as monocaprylin), glyceryl caprate (also known as monocaprrin), and glyceryl laurate (also known as monolaurate).

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

According to one embodiment of the present invention, for example, the fatty acid-ester mixture (a) may be obtained by directly partially esterifying the fatty acid component (a-I) with a polyol to form a monoester, thereby obtaining a mixture of the fatty acid and the corresponding monoester as the ester component (a-II). When polyols are used, it is well known that polyesters, such as diesters, triesters, and the like, may eventually be formed. Accordingly, fatty acid-ester mixtures (a) comprising at least 3 fatty acids, monoesters corresponding to said at least 3 fatty acids and polyesters corresponding to said at least 3 medium-chain fatty acids can still be used in the present invention, provided that the main objective, in particular the antipruritic effect, is not significantly impaired.

For the purposes of the present invention, the term "polyester" refers to an ester formed by esterification of a polyol, wherein more than one hydroxyl group of the polyol molecule is esterified. Accordingly, "diester" and "triester" according to the present invention mean the esterification of two and three hydroxyl groups, respectively, of a polyol molecule.

For example, when the fatty acid components (a-I) are esterified using glycerol, useful fatty acid-ester mixtures (a) may comprise at least 3 fatty acids, monoesters, diesters, and triesters corresponding to the at least 3 fatty acids. For example, useful fatty acid-ester mixtures (a) may comprise caprylic acid, capric acid and lauric acid as component (a-I); glyceryl monocaprylate, glyceryl monocaprate and glyceryl monolaurate as components (A-II); and diglycerides and triglycerides of caprylic acid, capric acid and lauric acid.

When the fatty acid-ester mixture (a) further comprises a polyester, the content of the polyester is not particularly limited as long as the main purpose of the mixture (a), particularly the antipruritic effect, is not significantly impaired. For example, polyesters may be used in mixture (a) in an amount of up to 90% by weight, preferably 80% by weight or less, or preferably 70% by weight or less, or preferably 65% by weight or less.

AVCO

According to one embodiment of the invention, for example, the fatty acid-ester mixture (a) may be of natural origin. Of these, coconut oil is well known to contain mixtures of various C8-C20 fatty acids, especially those having an even number of carbon atoms. Accordingly, it is desirable that the present invention use a derivative of coconut oil, for example, an esterified product of coconut oil, as the fatty acid-ester mixture (a).

Among the coconut oil derivatives that can be used are those known as Activated Virgin Coconut Oil (AVCO). Preferably, the coconut oil is esterified with glycerin. The AVCO useful according to the present invention may comprise caprylic acid, capric acid and lauric acid as components (a-I); glyceryl monocaprylate, glyceryl monocaprate and glyceryl monolaurate as components (A-II).

According to one embodiment of the present invention, for example, as usable AVCO, the total amount of fatty acids of component (a-I) and the total amount of monoglycerides of component (a-II) are present in a ratio of from 4:1 to 1:1, preferably from 3:1 to 1:1, more preferably from 2.5:1 to 1.5: 1. More specifically, for example, in exemplary embodiment 1 of the AVCO, a useful AVCO may comprise: fatty acid component (a-I): octanoic acid in an amount of 5 to 20 wt.%, preferably 7 to 15 wt.% or preferably 8 to 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 to 70 wt.%, preferably 30 to 60 wt.% or preferably 40 to 55 wt.%; and a monoester component (A-II): glyceryl monocaprylate in an amount of 0.5-15 wt%, preferably 1-10 wt% or preferably 4-7 wt%; glyceryl monocaprate in an amount of 0.1 to 10 wt.%, preferably 1 to 8 wt.% or preferably 3 to 5 wt.%; and glycerol monolaurate in an amount of 10-40 wt.%, preferably 15-35 wt.% or preferably 20-30 wt.%; each relative to the total amount of fatty acid component (A-I) and monoester component (A-II).

The AVCO obtained from esterification of coconut oil may further comprise diglycerides and triglycerides in addition to the above fatty acid component (a-I) and monoester component (a-II). According to one embodiment of the present invention, for example, useful AVCO may comprise caprylic acid, capric acid and lauric acid as components (a-I); glyceryl monocaprylate, glyceryl monocaprate and glyceryl monolaurate as components (A-II); and optionally, diglycerides and triglycerides of caprylic acid, capric acid, and lauric acid.

When the AVCO further comprises a polyester selected from the group consisting of diglycerides and triglycerides, the content of the polyester is not particularly limited, for example, an amount of at most 90% by weight, preferably 80% by weight or less, or preferably 70% by weight or less, or preferably 65% by weight or less.

According to one embodiment of the 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 glycerol monocaprylate, glycerol monocaprate and glycerol monolaurate in an amount of 1-30 wt%, preferably 5-20 wt% or preferably 10-15 wt%; 10-50 wt.%, preferably 20-45 wt.% or preferably 30-40 wt.% of the total amount of caprylic acid, capric acid and lauric acid diglycerides; and 10 to 70 wt.%, preferably 15 to 50 wt.% or preferably 20 to 30 wt.% of a total amount of triglycerides of caprylic acid, capric acid and lauric acid; each relative to the total amount of AVCO.

Useful AVCOs may preferably be AVCOs prepared according to the teachings of EP 1973415, the disclosure of which is incorporated herein by reference. Accordingly, an exemplary AVCO may 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 glyceryl monocaprylate, 8.29 mg/g glyceryl monocaprate and 57.16 mg/g glyceryl monolaurate; 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 glyceryl monocaprylate, 10.35 mg/g glyceryl monocaprate and 75.54 mg/g glyceryl monolaurate; each relative to the total weight of the AVCO; preferably, the AVCO is derived from catalyzing coconut oil with a1, 3-specific lipase and subjecting it to glycerolysis.

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

Cationic surfactant (B)

According to one embodiment of the present invention, the composition of the present invention may comprise at least one cationic surfactant which may be used 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 which may be mentioned in particular include:

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

in formula (V), the group R ₈ To R ₁₁ Which may be identical or different, represent a linear or branched aliphatic or aromatic radical comprising from 1 to 30 carbon atoms, such as an aryl or alkylaryl radical, the radical R ₈ To R ₁₁ At least one of (a) contains from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms. The aliphatic group may contain heteroatoms such as, inter alia, oxygen, nitrogen, sulfur and halogens.

The aliphatic radical being selected, for example, from C ₁ -C ₃₀ Alkyl radical, C ₁ -C ₃₀ Alkoxy, polyoxy (C) ₂ -C ₆ ) Alkylene radical, C ₁ -C ₃₀ Alkyl amides, (C) ₁₂ -C ₂₂ ) Alkylamide group (C) ₂ -C ₆ ) Alkyl, (C) ₁₂ -C ₂₂ ) Alkyl acetate, C ₁ -C ₃₀ Hydroxyalkyl radical, X ^- Is selected from the group consisting of halide, phosphate, acetate, lactate and (C) ₁ -C ₄ ) Alkyl sulfates and (C) ₁ -C ₄ ) Alkyl sulfonate or (C) ₁ -C ₄ ) Alkyl aryl sulfonates, preferably halide, such as fluoride, chloride, bromide, and the like, as the anionic counterion.

Among the quaternary ammonium salts of the formula (V), preference is first given to tetraalkylammonium halides, such as tetraalkylammonium chlorides, for example tetraalkylammonium or alkyltrimethylammonium halides, such as dialkyldimethylammoniumOr alkyltrimethylammonium chlorides, in which the alkyl group contains from about 12 to 22 carbon atoms, in particular halides, such as behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, benzyldimethylstearylammonium chloride, or secondly alkoxy sulfates, in particular distearoylethylhydroxyethylmethylammonium methylsulfate, dipalmitoylethylammonium methylsulfate or distearoylethylhydroxyethylammonium methylsulfate, or finally palmitoylamidopropyltrimethylammonium halides, in particular chlorides, or else ceramidyk, by the company Van Dyk, Ceraphyl ^® Stearamidopropyl dimethyl (myristyl acetate) ammonium chloride sold under the name stearamidopropyl dimethyl (myristyl acetate) 70;

-b) quaternary ammonium salts of imidazolines, such as those of formula (VI):

in formula (VI):

·R ₁₂ represents an alkenyl or alkyl group containing 8 to 30 carbon atoms, such as a fatty acid derivative of tallow;

·R ₁₃ represents a hydrogen atom, C ₁ -C ₄ An alkyl or alkenyl or alkyl group containing 8 to 30 carbon atoms;

·R ₁₄ represents C ₁ -C ₄ An alkyl group;

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

·X ^- represents in particular a halogen ion, phosphate, acetate, lactate, (C) ₁ -C ₄ ) Alkyl sulfate radical, (C) ₁ -C ₄ ) Alkyl sulfonate or (C) ₁ -C ₄ ) Anionic counterions to alkylarylsulfonates.

R ₁₂ And R ₁₃ Preferably, it refers to mixtures of alkyl or alkenyl groups containing 12 to 21 carbon atoms, e.g. derived from tallow fatty acid, R ₁₄ Preferably means methyl, and R ₁₅ Preferably, it is a hydrogen atom. For example, Rewo corporation as Rewoquat ^® W75 is the name selling this product;

-c) a quaternary diammonium or triammonium salt, in particular of formula (VII):

in formula (VII):

·R ₁₆ refers to an alkyl group containing from about 16 to 30 carbon atoms optionally hydroxylated and/or interrupted by one or more oxygen atoms;

·R ₁₇ selected from hydrogen, alkyl groups containing 1 to 4 carbon atoms or the 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 the same or different, are selected from hydrogen and alkyl groups containing 1 to 4 carbon atoms, and

·X ^- represents in particular a halogen ion, acetate, phosphate, nitrate, (C) ₁ -C ₄ ) Alkyl sulfate radical, (C) ₁ -C ₄ ) Alkyl sulfonate or (C) ₁ -C ₄ ) Alkylarylsulfonates, in particular the anionic counterions for methylsulfate and ethylsulfate. Such compounds are, for example, Finquat CT-P (Quaternium 89) available from the company Finetex and Finquat CT (Quaternium 75) available from the company Finetex;

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

in formula (VIII):

·R ₂₂ is selected from C ₁ -C ₆ Alkyl and C ₁ -C ₆ Hydroxyalkyl or dihydroxyalkyl;

·R ₂₃ selected from:

-group

-linear or branched, saturated or unsaturated C ₁ -C ₂₂ Hydrocarbyl radical R ₂₇ ，

-a hydrogen atom;

·R ₂₅ selected from:

-group

-linear or branched, saturated or unsaturated C ₁ -C ₆ Hydrocarbyl radical R ₂₉ ，

-a hydrogen atom;

·R ₂₄ 、R ₂₆ and R ₂₈ Which may be identical or different, are selected from linear or branched, saturated or unsaturated C ₇ -C ₂₁ A hydrocarbyl group;

r, s and t, which may be the same or different, are integers from 2 to 6;

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

y is an integer from 1 to 10;

x and z, which may be the same or different, are integers from 0 to 10;

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

provided that the sum x + y + z is from 1 to 15, R is 0 ₂₃ Is denoted by R ₂₇ And when z is 0, R ₂₅ Is denoted by R ₂₉ 。

Alkyl radical R ₂₂ May be linear or branched, more particularly linear.

Preferably, R ₂₂ Refers to methyl, ethyl, hydroxyethyl or dihydroxypropyl, more particularly methyl or ethyl.

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

When R is ₂₃ Is a hydrocarbyl radical R ₂₇ When it is used, it may be long and may contain 12 to 22 carbon atoms, or may be short and may contain 1 to 3 carbon atoms.

When R is ₂₅ Is a hydrocarbyl radical R ₂₉ When it is used, it preferably contains 1 to 3 carbon atoms.

Advantageously, R ₂₄ 、R ₂₆ And R ₂₈ Which may be identical or different, are selected from linear or branched, saturated or unsaturated C ₁₁ -C ₂₁ A hydrocarbon radical, more particularly selected from linear or branched, saturated or unsaturated C ₁₁ -C ₂₁ Alkyl and alkenyl groups.

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

Advantageously, y is equal to 1.

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

Anionic counterion X ^- Preferably a halide ion (preferably, for example, chloride, bromide or iodide), (C) ₁ -C ₄ ) Alkyl sulfate radical or (C) ₁ -C ₄ ) Alkyl sulfonate or (C) ₁ -C ₄ ) An alkylaryl sulfonate. However, methanesulfonate, phosphate, nitrate, tosylate, anions derived from organic acids, such as acetate or lactate, or any other anion compatible with the ammonium containing ester functionality may be used.

Anionic counterion X ^- Even more in particular chloride, methyl sulfate or ethyl sulfate.

More particularly, ammonium salts of formula (VIII) are used in the compositions according to the invention, wherein:

- R ₂₂ refers to a methyl group or an 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 selected from:

a group

Methyl, ethyl or C14-C22 hydrocarbyl groups,

a hydrogen atom,

- R ₂₅ selected from:

a group

A hydrogen atom,

- R ₂₄ 、R ₂₆ and R ₂₈ Which may be identical or different, are selected from linear or branched, saturated or unsaturated C ₁₃ -C ₁₇ A hydrocarbon radical, more particularly selected from linear or branched, saturated or unsaturated C ₁₃ -C ₁₇ Alkyl and alkenyl groups.

Advantageously, the hydrocarbyl group is linear.

Among the quaternary ammonium salts containing one or more ester functions of formula (VIII), examples which may be mentioned include salts of diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethylmethylammonium, monoacyloxyethyldihydroxyethylmethylammonium, triacyloxyethylmethylammonium or monoacyloxyethylhydroxyethyldimethylammonium, in particular the chlorides or methylsulfates, and mixtures thereof. The acyl group preferably contains 14 to 18 carbon atoms, more particularly obtained from a vegetable oil, such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be the same or different.

These products are obtained, for example, by direct esterification of optionally oxyalkylenated triethanolamine, triisopropanolamine, alkyldiethanolammines or alkyldiisopropanolamines with fatty acids or fatty acid mixtures of vegetable or animal origin, or by transesterification of their methyl esters. After this esterification, quaternization is carried out by means of alkylating agents, such as alkyl halides, preferably methyl or ethyl halides, dialkyl sulfates, preferably methyl sulfate or ethyl sulfate, methyl methanesulfonate, methyl p-toluenesulfonate, chloroethylene glycol (chlorohydrin) or chloroglycerol (chlorohydrin).

Such compounds are for example Dehyquart by Henkel ^® Named, Stepan company, Stepan quat ^® Noxamium, a company Ceca ^® Under the name Rewoquat or Rewoo-Witco ^® WE 18 is sold under the name.

The compositions according to the invention may contain, for example, a mixture of quaternary ammonium salts of mono-, di-and tri-esters, the majority by weight being diester salts.

It is also possible to use ammonium salts containing at least one ester function as described in patents US-A-4874554 and US-A-4137180.

Behenoylhydroxypropyltrimethylammonium chloride, sold by Kao under the name Quatarmin BTC 131, can be used.

Preferably, the ammonium salt containing at least one ester function contains two ester functions.

Some amines may provide cations when interacting with other agents, such as certain acids. In such cases, the particular amine may be classified as a useful cationic surfactant.

Preferred examples of useful cationic surfactants include non-silicone cationic surfactants including cetyltrimethylammonium, behenyltrimethylammonium, dipalmitoylethylmethylammonium, distearoylethylhydroxyethylmethylammonium, methyl (C9-C19) alkyl, (C10-C20) alkylamidoethylimidazolium, and salts of stearamidopropyldimethylamine, stearamidopropyldimethylammonium, and mixtures thereof.

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

According to one embodiment, among the cationic surfactants that may be present in the composition according to the invention, it is more particularly preferred to select stearamidopropyl dimethyl (myristyl acetate) ammonium chloride, cetyl trimethyl ammonium, behenyl trimethyl ammonium and dipalmitoyl ethyl hydroxyethyl methyl ammonium salts and mixtures thereof, more particularly stearamidopropyl dimethyl (myristyl acetate) ammonium chloride, behenyl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride and dipalmitoyl ethyl hydroxyethyl ammonium methyl sulfate and mixtures thereof.

Advantageously, the at least one cationic surfactant is present in a content ranging from 0.001% to 10% by weight, preferably from 0.005% to 5% by weight and more preferably from 0.01% to 3% by weight relative to the weight of the composition.

Additive oil

In addition to the fatty acids and esters thereof used in the fatty acid-ester mixture (a), the compositions according to the invention may optionally comprise additional oils conventionally used for cosmetic purposes.

The additional oil may be volatile or non-volatile.

The term "volatile oil" refers to any non-aqueous medium that evaporates from the skin or lips in less than 1 hour at room temperature (20-25 ℃) and atmospheric pressure (760 mmHg).

More specifically, the volatile oil may be a volatile cosmetic oil that is liquid at room temperature. More specifically, the volatile oil has a concentration of 0.01 to 200 mg/cm ² Evaporation rate between/min, endpoints included.

The term "non-volatile oil" means that the oil stays on the skin or keratin fibers at ambient temperature and atmospheric pressure. More particularly, the non-volatile oil has a viscosity of strictly less than 0.01 mg/cm ² Evaporation rate/min.

The additional oil may thus be liquid or solid at room temperature.

Additional oils suitable for use in the present invention may be hydrocarbyl, silicone-based or fluoro-based. According to a preferred embodiment of the invention, the composition is free of silicone-based oils.

According to the invention, the term "silicone oil" means an oil comprising at least one silicon atom, in particular at least one Si — O group.

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

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

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

More preferably, the composition of the present invention comprises a hydrocarbon oil.

In particular, the volatile oil may be chosen from hydrocarbon oils having from 8 to 16 carbon atoms, in particular branched C ₈ -C ₁₆ Alkanes (also known as isoparaffins or isoalkanes), such as isododecane (also known as 2,2,4,4, 6-pentamethylheptane), isodecane, isohexadecane and, for example, under the trade name Isopars ^® Or Permethyls ^® Oil sold.

As hydrocarbon volatile oils, mention may also be made of straight-chain C ₉ -C ₁₇ Alkanes, e.g. dodecane (C) ₁₂ ) And tetradecane (C) ₁₄ ) Respectively with PARAFOL ^® 12-97 and PARAFOL ^® 14-97 (Sasol) sold under the name of Sasol and obtained according to the process described in International application WO 2007/068371A 1, for example as CETIOL ^® Undecane (C) sold under the name UT (Cognis) ₁₁ ) And tridecane (C) ₁₃ ) And (3) mixing.

The non-volatile oil may be chosen in particular from non-volatile hydrocarbon oils.

According to a preferred embodiment, the composition of the invention comprises at least one oil chosen from vegetable oils, fatty alcohols or mixtures thereof.

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

As examples of vegetable oils suitable for use in the present invention, mention may be made of:

-a sweet almond oil, which is,

-a mixture of argan oil and argan oil,

-an oil of avocado oil,

-a peanut oil,

-a camellia oil, the camellia oil,

-a safflower oil, having a fatty acid skeleton,

-Malus spectabilis (calophyllum) oil,

-a source of coconut oil,

-a rapeseed oil,

coconut oil (copra oil),

-oil of coriander (Coriandrum sativum),

-a gourd oil,

-a wheat germ oil,

-jojoba oil or jojoba liquid wax,

-a linseed oil (Linum usitatissimum),

-a macadamia nut oil,

-a corn germ oil (CEV),

-a hazelnut oil,

-a source of walnut oil,

vernonia oil (vernonia oil),

-an almond oil, the almond oil,

-an olive oil, the olive oil having a fatty acid,

-an oil of evening primrose,

-a palm oil, the palm oil having a palm oil content,

-a passion flower oil, and-a water-soluble oil,

-a grape seed oil, which is selected from the group consisting of grape seed oil,

-a rose oil, which is a natural oil,

-a source of castor oil,

-a source of rye oil,

-a sesame oil,

-a rice bran oil, which is obtained by grinding,

soybean oil (soya oil), or soybean oil (soybean oil) and

-sunflower oil.

Preferably, the composition of the present invention may further comprise at least one vegetable oil selected from almond oil, soybean oil or mixtures thereof.

Examples of fatty alcohols useful in the compositions of the present invention include C8-C22 alcohols, preferably C16-C18 alcohols, such as octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, or mixtures thereof.

When they are present in the composition, the amount of additional oil is preferably from 0.01% to 20% by weight, better still from 0.05% to 10% by weight, more particularly from 0.1% to 5% by weight, relative to the total weight of the final composition.

Solvent(s)

The composition according to the invention may advantageously comprise one or more solvents, such as water and/or organic solvents, in the aqueous phase.

Water (W)

The composition according to the invention may advantageously comprise a content of water of 40% by weight relative to the total weight of the composition. The water content in the low viscosity composition according to the invention is preferably from 40 to 90 wt.%, more preferably from 50 to 90 wt.%, or from 60 to 85 wt.%, 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 (water solubility greater than or equal to 5% at 25 ℃ and at atmospheric pressure).

Examples of organic solvents which may be mentioned include linear or branched and preferably saturated monoalcohols or diols containing from 2 to 10 carbon atoms, such as ethanol, isopropanol, hexanediol (2-methyl-2, 4-pentanediol), neopentyl glycol and 3-methyl-1, 5-pentanediol, butanediol, dipropylene glycol and propylene glycol; aromatic alcohols such as phenethyl alcohol; polyols containing more than two hydroxyl functions, such as glycerol; polyol ethers such as ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol or ethers thereof, such as propylene glycol monomethyl ether; and diethylene glycol alkyl ethers, especially C ₁ -C ₄ Alkyl ethers, such as diethylene glycol monoethyl ether or monobutyl ether, alone or as a mixture.

When present, the organic solvent generally constitutes between 0.1% and 20% by weight, preferably between 0.2% and 10% by weight, or between 0.3% and 5% by weight, relative to the total weight of the composition according to the invention.

Additive

According to various embodiments, the composition of the invention is intended to be applied to keratin materials, such as the skin, the scalp or the hair. According to these embodiments, the compositions of the present invention may comprise various ingredients conventionally used in conditioning compositions for keratin materials, such as additional surfactants, including nonionic, anionic and amphoteric surfactants, active ingredients, moisturizers, additional fatty substances, antidandruff agents, anti-seborrheic agents, agents to prevent hair loss and/or promote hair regrowth, vitamins and provitamins, including panthenol, sunscreens, sequestering agents, plasticizers, acidulants, opacifying agents, pearlizing agents (pearlescence agents), antioxidants, hydroxy acids, fragrances and preservatives.

A non-exhaustive list of these components can be found in U.S. patent application publication No. 2004/0170586, which is incorporated herein by reference in its entirety. Further examples of such additional ingredients can be found inInternational Cosmetic Ingredient Dictionary and Handbook(9 th edition 2002).

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

These additives can be variously selected by those skilled in the art to prepare compositions having desired properties, such as consistency or texture. In particular, the additives (if used) and their amounts are determined inter alia on the basis of the specific product/its application, e.g. leave-on conditioners, rinse-off conditioners, skin care conditioners, etc.

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

Method and use

The compositions according to the invention can generally be prepared according to the general knowledge of a person skilled in the art. Nevertheless, it will be understood that the person skilled in the art may select a preparation method on the basis of his general knowledge, taking into account the properties of the ingredients used, such as their solubility in the carrier and the application envisaged for the composition or kit.

According to one embodiment, the composition according to the invention can be used for caring for keratin materials, in particular the skin, the scalp and/or the hair. Such use may be represented by a method for caring for keratin materials, in particular the skin, the scalp and/or the hair, comprising the step of applying the composition of the invention to said keratin materials.

The compositions according to the invention are preferably useful for formulating hair conditioner products, scalp care products or even skin care products. Also in light of the above detailed discussion, it is to be understood that the compositions according to the present invention, and thus shampoo products, may be free of silicone oil.

The keratin fiber conditioning compositions 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, lotions, mousses, and sprays. The compositions of the present invention are particularly useful in post-shampoo conditioners.

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

For example, when used as a post-shampoo conditioner, the compositions of the present invention may be applied by a process comprising the steps of:

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

(ii) rinsing the hair.

The invention is further illustrated by the following examples, which illustrate particularly advantageous embodiments.

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

Examples

The amounts/concentrations of the ingredients in the compositions/formulations described below are expressed in weight% relative to the total weight of each composition/formulation.

Materials:

COCOS NUCIFERA (coconut) oil Activated Virgin Coconut Oil (AVCO) available from BIOTROPICS

Other materials not described herein are each commercially available.

Example 1

Compositions a and comparative compositions C as in table 1 were prepared:

TABLE 1

INCI	Composition A	Composition C
			Rape oleamide propyl dimethylamine	1.5	1.5
Stearic acid glyceride	0.5	0.5
			Cetostearyl alcohol	7	7
Stearyl alcohol	1.5	1.5
			Octanediol	0.3	0.3
COCOS NUCIFERA (COCONUS) OIL	0.9	-
			Helianthus ANNUUS seed oil	2	2
Tartaric acid	0.3	0.3
			Perfume	0.6	0.6
Water (W)	QS to 100	QS to 100

The above listed compositions a and C were prepared according to manufacturing methods known in the art.

Example 2

The soothing feel of composition a was evaluated. 5 volunteers 25 to 45 years old applied composition a daily to the hair and scalp for 3 weeks, followed by 2 weeks without composition a. Itching (soothing) was assessed over a total of 5 weeks. The score of itching sensation before application of composition a was given as baseline and the score of itching sensation after application of composition a was given daily, with the average difference shown in table 2.

The scores are given and calculated as follows:

in the first 3 weeks, each volunteer was shampooed every night with composition a, using the usual usage of each volunteer. In the next 2 weeks, each volunteer was also shampooed every night with a standard shampoo without AVCO, with the normal usage of each volunteer still being used.

Volunteers gave scores for itching sensation, where:

0 means unchanged;

-1 means moderate improvement;

-2 means a significant improvement; and

-3 means essentially no itching sensation.

The average score of 5 volunteers was counted daily and the weekly average was calculated. The average score for a total of 5 weeks is provided in table 2 below.

TABLE 2

	Week 1	Week 2	Week 3	Week 4	Week 5
						Composition A	-0.8	-1.1	-1.6	-1.4	-1.2

Referring to table 2, the lower the score, the less itching. It was observed that composition a exhibited a very good and long-lasting scratchiness even 2 weeks after the last application of the composition.

Claims

1. A composition for conditioning keratin materials comprising:

an oil phase comprising

(A) A fatty acid-ester mixture comprising:

(B) at least one cationic surfactant.

2. The composition according to claim 1, wherein the fatty acid-ester mixture (a) comprises at least 3 fatty acids selected from caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and arachidic acid, for use as component (a-I); and the corresponding glyceride of each fatty acid in component (A-I) is used as component (A-II);

preferably, the fatty acid component (a-I) comprises caprylic acid, capric acid and lauric acid; and the corresponding components (A-II) comprise glycerol monocaprylate, glycerol monocaprate and glycerol monolaurate; 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 of 4:1 to 1:1, preferably 3:1 to 1:1, more preferably 2.5:1 to 1.5: 1.

3. A composition according to claim 1 or 2, wherein the fatty acid-ester mixture (a) is activated virgin coconut oil comprising:

-fatty acid component (a-I):

octanoic acid in an amount of 5 to 20 wt.%, preferably 7 to 15 wt.% or preferably 8 to 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):

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

glyceryl monocaprate in an amount of 0.1 to 10 wt.%, preferably 1 to 8 wt.% or preferably 3 to 5 wt.%; and

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

each relative to the total amount of fatty acid component (A-I) and monoester component (A-II).

4. A composition according to claim 3, wherein the activated virgin coconut 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 glycerol monocaprylate, glycerol monocaprate and glycerol monolaurate in an amount of 1-30% by weight, preferably 5-20% by weight or preferably 10-15% by weight;

-10-50 wt.%, preferably 20-45 wt.% or preferably 30-40 wt.% of the total amount of caprylic acid, capric acid and lauric acid diglycerides; and

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

each relative to the total amount of activated virgin coconut oil.

5. 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 from 0.1% to 5% by weight, or preferably from 0.5% to 3% by weight, or preferably from 0.8% to 1.5% by weight, relative to the total weight of the composition.

6. Composition according to any one of the preceding claims, in which the at least one cationic surfactant (B) is chosen from primary, secondary or tertiary fatty amine salts, optionally polyoxyalkylenated, quaternary ammonium salts and mixtures thereof, preferably chosen from stearamidopropyldimethyl (myristyl acetate) ammonium chloride, cetyl trimethylammonium, behenyl trimethylammonium and dipalmitoyl ethylhydroxyethylmethylammonium salts and mixtures thereof.

7. Composition according to any one of the preceding claims, in which the cationic surfactant (B) is present in the composition in an amount ranging 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.

8. Composition according to any one of the preceding claims, further comprising at least one additional oil chosen from C8-C22 alcohols, preferably C16-C18 alcohols, such as octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol or mixtures thereof.

9. Composition according to any one of the preceding claims, in which the at least one additional oil is present in the composition in an amount ranging 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 composition, including all ranges and subranges therebetween.

10. Composition according to any one of the preceding claims, which is free of silicone-based oils.

11. A hair conditioner product comprising a composition according to any preceding claim 1 to 10.

12. A scalp care product according to claim 12 which is a leave-on hair conditioner product or a rinse-off hair conditioner product.

13. A scalp care product comprising a composition according to any preceding claims 1 to 10.

14. A skin care product comprising a composition according to any of the preceding claims 1 to 10.