FR3038835A3 - SHAMPOO COMPOSITION COMPRISING AT LEAST ONE OLIGOESTER AMMONIUM SALT - Google Patents

Abstract

The present invention relates inter alia to shampoo compositions comprising an oligoester ammonium salt (OAS) and a cosmetically (F) component, the OAS being obtained by: (i) heating a mixture of the components (a) to (d) below, with continuous removal of the water of reaction: (a) a certain diethanolamine compound; (b) a certain dicarboxylic acid; (c) a certain organic triol; and a monocarboxylic acid of formula R1-COOH (d), wherein R1 is a straight or branched chain C12-C24 alkyl group; (ii) reacting the oligoester of step (i) with a quaternizing agent.

Description

Shampoo composition comprising at least one ammonium salt of oligoester

The present invention relates to shampoo compositions comprising at least one oligoester ammonium salt, methods for preparing the shampoo compositions, their use, and methods of treating the hair.

The processes for cleaning and conditioning the hair have been known for centuries. Frequently, the cleaning processes require an alkaline agent, such as a soap. The interaction of this agent with the hair leads to a weakening of their mechanical properties and increases the porosity of the hair fibers. Many known shampoo components lead to dry hair, which is damaged. This can lead to a dull appearance of the hair, and result in a greater number of washes than necessary. Frequent washing of hair can lead to more damaged and less conditioned hair.

To improve the condition of the hair and keep the hair looking natural over a longer period of time, improved hair shampoos with conditioning properties are needed. In particular, the force required for combing and combing hair is an important feature. The standard product formats are rinse-removable shampoos, which are usually based on foaming surfactants (silicone or non-silicone, opaque or transparent), cleaning conditioners usually based on cationic surfactants, or no-poo / low products. -poo / light-poo (no shampoo / little shampoo / light shampoo), with reduced levels of foaming surfactants.

Natural oils have been used for centuries to condition human hair. Essential oils (eg tea tree oil) and carrier oils (eg jojoba oil) have been used. Human hair contains about 97% of the protein keratin, which must be protected to maintain their strength and natural appearance.

The surface of keratin contains negatively charged amino acids. For this reason, shampoos with hair conditioning properties may contain cationic components (eg, surfactants) that are not completely washed off. The hydrophilic ends of the cationic components can bind to keratin, while the hydrophobic ends of the molecules protect the surface of the hair.

The modern compositions of hair conditioning shampoos are often intended to soften the hair, improve the shine of hair and avoid a greasy appearance of the hair. Silicone derivatives, and quaternary ammonium compounds (surfactants or polymers), which coat the cuticle of hair, are used as conditioning ingredients in shampoo compositions. These shampoos can be made transparent or opaque.

Hair shampoo compositions generally comprise one or more of the following types of ingredients (components): surfactants (ionic or nonionic or amphoteric), containing polymers with a cleaning and foaming function, for thickening and stabilizing the formulation. Salt can also be used to increase the viscosity of the shampoo. conditioning agents (such as silicones, for example dimethicone or cyclomethicone, cationic polymers, cationic surfactants, etc.), which make the hair easier to disentangle and brighter. actives, such as anti-dandruff agents, for example piroctone olamine, zinc-pyrithione, selenium sulphide, climbazole, etc. - acidity regulators, which maintain the pH of the shampoo at about 4 to 7; antistatic agents; lubricants, such as fatty alcohols or provitamines such as panthenol; - humidifiers, which maintain the moisture of the hair and often contain humectants; oils (for example natural essences) for softening and softening the hair; - preservatives, to prevent the proliferation of microorganisms in the composition; sequestering agents, to improve the function of the composition in hard water; fortifiers, which often contain a hydrolysed protein, to penetrate the hair and strengthen the structure, for example by crosslinking polymers; - Sun protection agents, against a degradation of proteins and a loss of color, for example benzophenone.

Among many market trends, not only in cosmetics, it has been observed that green products (also known as green, natural or eco-friendly products) attract more consumers than before. To provide these products, ingredients are sought, having good biodegradability, low irritation potential, no allergenicity, and low impact on the environment. Often, these products are based on the chemistry of (poly) esters, which can hydrolyze and degrade in aquatic environments. Esterquats are available from German manufacturers such as Evonik or BASF.

DE-A 19 710 155 discloses a microemulsion comprising polyester ammonium salts of the general formula (H),

wherein R2 is a C1-C21 alkyl group, R3 is C1-C4 alkyl or hydroxyethyl, n is 1 to 7, y is 0 or 1, and [A] is halogen or methylsulfate.

A conditioning agent is proposed, and it is said that the application of a microemulsion for hair conditioning provides typical conditioning benefits, such as improved smoothness, flexibility and ease of combing hair. wet.

DE-C 19 743 687 discloses a detergent composition comprising ester ammonium salts of the general formula (K),

wherein R1 is a C5-C21 alkyl group; R2 is a C1-C4 alkyl group; R3 is selected from C1-C4 alkyl or hydroxy-C1-C4 alkyl; m is from 1 to 10; and n1, n2, n3, n4 are from 0 to 4.

It further states that the use of the composition for hair conditioning leads to a reduction of electrostatic charges, ease of combing wet and dry hair and improved flexibility. All these effects are all typical of conditioning agents.

As a result, the ammonium salts of esters, both (H) and (K), are said to produce typical effects of conditioning agents. There is nothing about other properties of this type of compounds. US 7,101,538 discloses a topical composition for the treatment of skin, hair and nails containing an amine component of polyesters. EP-A-1 160 238 discloses a process for the preparation of polyester-quats. The application WO 2003/063 790 describes various types of oligoester components for cosmetic applications. Shine, gloss, and surface smoothness are all desirable characteristics of cosmetic compositions and personal care preparations. For example, shine and gloss are highly desirable characteristics in nail polish and hair care preparations. Surface smoothness is important in shampoos, hair conditioners and other preparations for hair treatment and can provide better (easier) combing of wet, dry hair. However, these characteristics are often only achieved by combining several different ingredients in the cosmetic compositions. Thus, there is still a great need, in the context of personal care, for new compositions and / or components, which achieve several effects simultaneously, such as many of the features and advantages mentioned above. In particular, there is an important need for the provision of compositions and components that simultaneously provide excellent performance as a shampoo and a wide variety of cosmetic benefits.

An object of the present invention is to provide shampoo compositions comprising an ingredient which simultaneously provides a plurality of effects. Preferably, the composition and its components can be prepared easily, and provide or enhance many of the following benefits: hair combing, improved combing of wet and dry hair, shine (shine), such as hair shine without the need silicone, conditioning, surface smoothness (hair), hair repair, water resistance, film forming properties, static charge reduction, anti-crimp, volume, thickening and surfactant activity.

In a first aspect, the problems mentioned in the invention are solved by a shampoo composition comprising at least one oligoester ammonium salt (OAS) and at least one additional cosmetically acceptable component (F), the salt or salts thereof. oligoester ammonium (OAS) obtainable by the following steps: (i) heating a mixture of components (a) to (d) below, with continuous removal of the water of reaction: 0.5 at 3.0 mole equivalents, often 0.75 to 3.0 mole equivalents, of a diethanolamine compound represented by the formula (a)

wherein R3 is a straight or branched chain C1-C6 alkyl group, preferably a straight or branched chain C1-C4 alkyl group, more preferably methyl or ethyl; 0.5 to 1.5 mole equivalents of a dicarboxylic acid represented by the formula (b)

wherein R2 is straight or branched chain C1-C10 alkylene or straight or branched chain C2-C10 alkenylene, preferably C2-C8 alkylene, more preferably C4 alkylene; 0.5 to 1.5 mole equivalents of an organic triol represented by formula (c1) or (c2)

(c1) (c2) wherein R4 is a hydrogen atom or a straight or branched chain C1-C4 alkyl or hydroxyl- (C1-C4) alkyl group, preferably a hydrogen atom, the methyl group or ethyl, more particularly a hydrogen atom; 1.0 mole equivalent of a monocarboxylic acid represented by the formula (d) R1-COOH (d) wherein R1 is a straight or branched chain C12-C24 alkyl or straight chain C12-C24 alkenyl group or branched, preferably straight or branched chain C 12 -C 22 alkyl or straight or branched chain C 12 -C 22 alkenyl, more particularly C 20 -C 22 alkyl; (ii) reacting the oligoester product of step (i) with a quaternizing agent (e), in particular the dimethyl sulfate group, diethyl sulfate and alkyl halides; (iii) optionally, isolating and purifying the oligoester ammonium salt (s).

OAS (and the cosmetic composition) is preferably prepared, in which the R 3 radical of the diethanolamine component (a) is the methyl group.

The OAS (and the shampoo composition) is preferably prepared in which the dicarboxylic acid (b) is selected from the group consisting of adipic acid, glutaric acid, succinic acid, sebacic acid, itaconic acid, maleic acid and combinations thereof.

OAS (and the shampoo composition) is preferably prepared, wherein the organic triol (c) is selected from the group consisting of glycerol, triethanolamine and combinations thereof.

The OAS (and the shampoo composition) is preferably prepared by selecting the carboxylic acid (d) selected from the group consisting of behenic acid, oleic acid, fatty acid derived from coconut oil. , linoleic acid and combinations thereof.

OAS (and the shampoo composition) is preferably prepared by selecting component (a), (b), (c) and (d) in the following molar ratios: 0.5 to 3.0 (a). ), from 0.5 to 1.5 (b), from 0.5 to 1.5 (c) and 1 (d). Component (a) may also preferably be used in a mole ratio of 0.75 - 3.0.

The OAS (and the shampoo composition) is preferably prepared by choosing the molar ratio of the components (a), (b), (c) and (d) so that the mole equivalents of the hydroxyl functions are in excess relative to the mole equivalents of the acid functions.

The OAS (and the shampoo composition) is preferably prepared by choosing a method in which the mixture of components (a), (b), (c) and (d) is first heated in step (i) at a temperature of 80 to 220 ° C, preferably from 150 to 210 ° C, more preferably from 160 to 200 ° C, and in step (ii) a subsequent reaction of the obtained oligoester product takes place with a quaternizing agent (e), preferably selected from the group consisting of dimethyl sulfate, diethyl sulfate, methyl chloride, ethyl chloride, butyl chloride and combinations thereof.

The shampoo composition is preferably prepared in which the oligoester ammonium salt (OAS) has a molecular weight Mn (number average) of 500 to 4000 g / mol, preferably 600 to 4000 g / mol more preferably from 650 to 2000 g / mol, more preferably from 665 to 1800 g / mol.

In a particularly preferred embodiment of the first aspect, components (a) to (c) are respectively: methyldiethanolamine (component (a)), behenic acid (component (d)), adipic acid or sebacic acid (component (b)) and glycerol (component (c)).

In a second aspect, the invention also relates to a shampoo composition comprising at least one oligoester ammonium salt (OAS) of formula (I) and at least one additional cosmetically acceptable component (F),

wherein: R1 is a straight or branched chain C12-C24 alkyl group or a straight or branched chain C12-C24 alkenyl group; R2 is a straight or branched chain C1-C6 alkylene group or a straight or branched chain C2-C8 alkenylene group; A is, at least once, independently selected from compounds satisfying the groups: (C 1 -C 6 alkylene) -CR 5 R 6 - (ylène-ι-β alkylene), preferably (C 1 -C 4 alkylene) -CR 5 R 6 - ( C1-C4 alkylene), wherein R5 and R6 are each independently selected from the group consisting of H, OH, C1-C6 alkyl and hydroxy-en-ι-Ο-alkyl; and is, at least once, independently selected from quaternary ammonium compounds of formula (II)

wherein R3 and R4 each independently represent straight or branched chain C 1-6 alkyl or straight or branched chain hydroxy-C 1-6 alkyl group; n is an integer of 1 to 30, preferably 1 to 10; and m is an integer of 1 to 31, describing the charge, preferably m is an integer of 1 to 10; [(Xp ") i / P] is a counterion selected from the group consisting of monovalent anions of formula [X '], divalent anions of formula [(X2') o, s], and trivalent anions of [(X3 ') i / 3] The expression "A is at least once independently selected from" means that the compound satisfying formula (I) must contain, on the A-position, a compound satisfying the In fact, since n is an integer from 1 to 30, not all the repeating units described in the square brackets for n need be exactly the same from a chemical point of view. when n is 3, then A, described in square brackets for n, could be three different chemical groups, or the same chemical group The expression "A is, at least once, independently selected from" means that the compound satisfying the formula (I) must contain, on the position A, at least once a compound satisfying the requirements described below - when nv aut 3, then A could be said compound for all repeating patterns, or only for one occurrence of A - the minimum was at least once.

In at least one embodiment of the shampoo composition, in formula (I), group A satisfies (C 1 -C 4 alkylene) -CR 5 R 6 - (C 1 -C 4) alkylene, wherein R 5 and R 6 are each independently selected from the group consisting of H, OH, C1-C2 alkyl groups and hydroxymethyl group.

At least one embodiment relates to a shampoo composition in which, in the formula (I), the compounds satisfying (C 1 -C 6 alkylene) -CR 5 R 6 - (en-ι-β alkylene) are selected from the group consisting of in: -CH2-CH [OH] -CH2-, -CH2-CH [CH2OH] -CH2-, -CH2-C [CH3] [CH2OH] -CH2-, -CH2-C [CH2CH3] [CH2OH] -CH2 -, and -CH2-C [CH2OH] 2 -CH2-.

In at least one embodiment of the shampoo composition, in formula (I), the group A is, at least once, independently selected from compounds satisfying (C1-C4) alkylene -NR7- (alkylene) C1-C4), where R7 is hydroxy-C1-C2alkyl.

In at least one embodiment of the shampoo composition, in formula (I), the counter-ion of formula [(Xp ') i / P] is selected from the group consisting of Cl (chloride), Br (bromide) ), MeSCV (methylsulfate), EtSCU (ethylsulfate), HC02 (formate), citrate, acetate, nitrate, [(CO32 ') o, s] (carbonate), [(S042') o, s] (sulfate), [ (P043 ') i / 3] (phosphate), and combinations thereof.

A third aspect relates to the use of an oligoester ammonium salt (OAS) obtained by a process as defined above, or an oligoester ammonium salt (OAS) of formula (I) as a surfactant in cosmetic compositions, preferably in shampoo compositions.

A fourth aspect relates to a process for preparing a shampoo composition, comprising the steps of preparing one or more oligoester ammonium salts (OAS) as described above, and mixtures of OAS to one or more other components (F) and water.

A fifth aspect relates to a hair treatment method, comprising: a) applying the shampoo composition according to the first aspect and the second aspect to the wet hair, and then b) removing the hair shampoo composition.

At least one embodiment of the fifth aspect relates to a hair treatment method, comprising: (a) applying the shampoo composition to the hair; then (b) washing the hair with the shampoo composition; then (c) removing the shampoo composition from the hair; and (d) optionally, applying a hair conditioner composition to the wet hair, and optionally removing the hair conditioner composition.

In the context of the present invention, the term "C1-C24 alkyl" embraces all types of acyclic and cyclic alkyl groups having 1 to 24 carbon atoms. In at least one embodiment, the C1-C24 alkyl-satisfying compounds are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2 ethylbutyl, 1-ethyl-1-methyl-propyl, 1-ethyl-2-methylpropyl, 2-ethyl-1-methyl-propyl and 2-ethyl-2-methylpropyl, n-heptyl, 5-methylhexyl, 2-ethyl 3-methylbutyl, n-octyl, 5-methylheptyl, 4,4-dimethylhexyl, 3-ethylhexyl, 2-ethyl-3-methylpentyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl , nona decyl, eicosanyl, henicosanyl, docosanyl, tricosanyl, tetracosanyl, as well as cyclopropyl, cyclobutyl, cyclopentyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclohexyl, 1-methyl-cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, 1, 2-dimethylcyclobutyl, 1,3-dimethylcyclobutyl, 2,2-dimethylcyclobutyl, 2,3-dimethylcyclobutyl and 3,3-dimethylcyclobutyl, cyclodecyl, decinyl, and mixtures thereof.

In the context of the present invention, the term "C2-C24 alkenyl" embraces all types of acyclic and cyclic hydrocarbon groups having 2 to 24 carbon atoms and one or more CC double bonds. In at least one embodiment, C2-C24 alkenyl-satisfying compounds are selected from the group consisting of vinyl, prop-1-enyl, prop-2-enyl, methallyl, 1-methylallyl, homoallyl, butyl, and the like. 2-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, 1-methylbut-1-enyl, 2-methylbut-1-enyl, 3-methylbut-1-enyl, 1-methylbut- 2-enyl, 2-methylbut-2-enyl, 3-methylbut-2-enyl, 1-methyl-but-3-enyl, 2-methylbut-3-enyl, 3-methylbut-3-enyl, 1-ethylpropyl 1-enyl, 1-ethyl-prop-2-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, 1-methylpent-1 enyl, 2-methylpent-1-enyl, 3-methylpent-1-enyl, 4-methylpent-1-enyl, 1-methylpent-2-enyl, 2-methylpent-2-enyl, 3-methylpent-2-enyl, 4-methylpent-2-enyl, 1-methylpent-3-enyl, 2-methylpent-3-enyl, 3-methylpent-3-enyl, 4-methylpent-3-enyl, 1-methylpent-4-enyl, 2- methylpent-4-enyl, 3-methylpent-4-enyl, 4-methylpent-4-enyl, 1,2-dimethyl thylbut-1-enyl, 1,3-dimethylbut-1-enyl, 3,3-dimethylbut-1-enyl, 1,1-dimethylbut-2-enyl, 1,2-dimethylbut-2-enyl, 1,3-dimethylbut-1-enyl, dimethylbut-2-enyl, 2,3-dimethylbut-2-enyl, 1,1-dimethylbut-3-enyl, 1,2-dimethylbut-3-enyl, 1,3-dimethylbut-3-enyl, 2,2- dimethylbut-3-enyl and 2,3-dimethylbut-3-enyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicenyl, henicenyl, docenyl, tricosenyl, tetracenyl, and cyclobut-1-enyl, cyclobut-2-enyl, cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl , cyclodecenyl, and mixtures thereof.

In the context of the present invention, the term "C1-C10 alkylene" embraces all types of saturated acyclic hydrocarbon units having the formula CmH2m, all types of saturated monocyclic hydrocarbon units having the formula CmH2m 2 and all types of saturated bicyclic hydrocarbon units having the formula CmH2m-4, wherein m in said formulas is whenever possible an integer selected from 1 to 10. In at least one embodiment, the C1-C10 alkylene-satisfying compounds are selected in the group consisting of methylene, ethylene, n-propylene, 1-methylethylene, 2-methylethylene, butylene, 1-methylpropylene, butylene, 2-methylpropylene, 3-methylproylene, 1,1-dimethylethylene, 1,2 dimethylethylene, pentylene, 1-methylbutylene, 2-methylbutylene, 3-methylbutylene, 1,1-dimethylpropylene, 2,2-dimethylpropylene, 1,2-dimethylpropylene, 1-ethylpropylene, hexylene, 1-methylpe ntylene, 2-methylpentylene, 3-methylpentylene, 4-methylpentylene, 1,1-dimethylbutylene, 1,2-dimethylbutylene, 1,3-dimethylbutylene, 2,2-dimethylbutylene, 2,3-dimethylbutylene, 3,3-dimethylbutylene, 1-dimethylbutylene, ethylbutylene, 2-ethylbutylene, 1-ethyl-1-methylpropylene, 1-ethyl-2-methylpropylene, 2-ethyl-1-methylpropylene, 2-ethyl-2-methylpropylene, heptylene, 5-methylhexylene , 2-ethyl-3-methylbutylene, octylene, 5-methyl-heptylene, 4,4-dimethylhexylene, 3-ethylhexylene, 2-ethyl-3-methylpentylene, nonylene and decylene, as well as 1,3-cyclopentylene, 1 , 3-cyclohexylene, decinylene, and mixtures thereof.

In the context of the present invention, the term "C2-C10 alkenylene" embraces all types of mono-unsaturated acyclic hydrocarbon units having the formula CmH2m 2, all types of di- and polyunsaturated acyclic hydrocarbon units having the formulas CmH2m -4, CmH2m6 etc., as well as cyclic mono- or di-unsaturated hydrocarbon units having the formulas CmH2m 4, CmH2m 6 etc., where m, in the formulas, is an integer chosen whenever possible between 2 and 10. In at least one embodiment, the C2-C10 alkenylene-satisfying compounds are selected from the group consisting of ethenylene, prop-1-enylene, prop-2-enylene, but-1-enylene, but-2- enylene, but-3-enylene, pent-1-enylene, pent-2-enylene, pent-3-enylene, pent-4-enylene, pent-5-enylene, 1-methylbut-1-enylene, 1-methylbut- 2-enylene, 1-methylbut-3-enylene, hex-1-enylene, hex-2-enylene, hex-3-enylene, hept-1-enylene, hept-2-enylen e, hept-3-enylene, oct-1-enylene, oct-2-enylene, oct-3-enylene, oct-4-enylene, non-1-enylene, non-2-enylene, non-3-enylene, non-4-enylene, dec-1-enylene, dec-2-enylene, hexa-1,3-dienylene, hexa-2,4-dienylene, hexa-1,3,5-trienylene, 1,3-cyclopent- 4-enylene, 1,3-cyclohex-4-enylene, and mixtures thereof.

Preferably, each R 1 in the oligoester ammonium salt of formula (I) is independently selected from compounds which are straight or branched chain C 12 -C 24 alkyl groups. More particularly, each R 1 is independently selected from compounds that are straight or branched C 16 -C 22 alkyl groups. In a more preferred embodiment of the present invention, R 1 is a C 17 alkyl group which may be for example the alkyl portion of isooctadecanoic acid, still more preferably the alkyl portion of isostearic acid. In another preferred embodiment, R 1 is a C 21 alkyl group, which may be the alkyl portion of behenic acid.

Preferably, -R 2 -, in the oligoester ammonium salt, is independently selected from compounds which are straight-chain - (C2-C8 alkylene) groups. More particularly, the compounds which are straight-chain C 2 -C 6 alkylene groups are selected from the group consisting of -CH 2 -CH 2 - (ethylene), -CH 2 -CH 2 -CH 2 - (propylene), - CH2-CH2-CH2-CH2- (butylene), -CH2-CH2-CH2-CH2-CH2- (pentylene), -CH2-CH2-CH2-CH2-CH2-CH2- (hexylene), and mixtures thereof. Particularly preferred are-R2-CH2-CH2-CH2-CH2-, or -CFh-CFh-CFh-CFh-CFh-CH2.

In at least one embodiment of the present invention, in the oligoester ammonium salt, R 3 is a - (C 1 -C 4) alkyl group.

In the oligoester ammonium salt, R4 is preferably selected from hydrogen, methyl or ethyl. More particularly, R4 is methyl.

In the context of the present invention, the letter "n" in the general formula (I) defines the average number of repeating units of the ammonium salts of oligoester. The number n is preferably an integer of 1 to 30, more preferably 1 to 10.

In the oligoester ammonium salt of general formula (I), the counterion [(Xp ') i / P] of the (m) -loaded oligoester ammonium cation is preferably selected from the group consisting of Cl (Chloride), Br- (bromide), MeSCU (methyl sulfate), EtSCV (ethylsulfate), HC02 (formate), citrate, acetate, nitrate, [(CO32 ') o, s] (carbonate), [(SO4. 2) 0.5] (sulfate), [(PO4.3) 1/3] (phosphate) and combinations thereof.

The shampoo composition also comprises one or more cosmetically acceptable components (F), which may be present in an amount of at least 0.5% by weight, or 0.5 to 20% by weight based on the total weight of the composition of shampoo. Preferably, component (F) is selected from the group consisting of cleansing ingredients, acidity regulators, coloring agents, additional conditioning agents, emulsifiers, film formers, fragrances, gloss agents, humectants, lubricants, humectants, pigments, preservatives, hair penetration enhancers, scalp actives, stabilizers, additional surfactants, thickeners, viscosity modifiers, and combinations of those -this. More particularly, component (F) is selected from the group consisting of surfactants, viscosity modifying polymers and conditioning ingredients. In at least one embodiment, the shampoo composition comprises from 1 to 20% by weight of one or more oligoester ammonium salts (OAS) and further comprises at least 0.5% by weight of a or more additional components (F) selected from the group consisting of surfactants, polymers, conditioners, actives, acid regulators, lubricants, humectants, oils, preservatives, sequestering agents, fortifiers, solar protectors and combinations thereof.

In at least one embodiment, the shampoo composition comprises a cosmetically acceptable supplemental component (F), which is a cleaning ingredient. In at least one embodiment, the shampoo composition comprises from 0.05% to 20% cleaning ingredients. In at least one embodiment of the shampoo composition, the content of the cleaning ingredient is 1% to 20% based on the total weight of the active ingredient of the composition, preferably 5 to 18%, more especially from 8 to 16%. In at least one embodiment, the cleaning ingredient is selected from the group consisting of non-polymeric surfactants, saponins, polymeric surfactants and combinations thereof. Preferably, the cleaning ingredient comprises or consists of surfactants.

In at least one embodiment, the shampoo composition preferably comprises from 0.01 to 20% by weight of one or more OAS and at least 0.5% by weight of one or more additional surfactants, preferably anionic or nonionic cleaning surfactants, such as sodium laureth sulphate, sodium lauryl sulphate, ammonium laureth sulphate, ammonium lauryl sulphate, olefinsulfonates, olefinsulfates, laureth-3 or 4, coconut -amide DEA, glucosides, cocoamidopropylbetaine, coco-betaine, coco-amphodipropionate, sodium methyl-2-sulfolaurate, and other laurates, sulfoacetates, sulfosuccinates, lactylates, sultaines, caprylates / caprates, isethionates, glutamates, taurates, sarcosinates, glucamides and combinations thereof.

In at least one embodiment, the composition comprises a surfactant system. In at least one embodiment, the surfactant system comprises a surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, zwitterionic surfactants and / or amphoteric surfactants.

In at least one embodiment, the composition comprises a total amount of the surfactant of from 0.01% by weight to 70% by weight, from 0.1% by weight to 40%, from 1% by weight to 30%, and 2% by weight to 20% by weight.

In at least one embodiment, the composition comprises an anionic surfactant. In at least one embodiment, the anionic surfactant is selected from the group consisting of (C 1 -C 10 alkyl) alkoxycarboxylates, alkyl ether carboxylates, (fatty alcohol) sulfates, (fatty alcohols) - ethersuliates, alkylamide-sulphates and sulphonates, (fatty acids) -alkylamide-polyglycol ether sulphates, alkane sulphonates and hydroxyalkane sulphonates, olefin sulphonates, acyl esters of isethionates, α-sulphonated fatty acid esters, alkyl benzene sulphonates , alkylphenol-glycolether-sulfonates, sulfosuccinates, monoesters and sulfosuccinic diesters, (fatty alcohols) -etherphosphates, protein / fatty acid condensation products, alkyl-monoglyceride-sulfates and -sulfonates, alkylglyceride-ether sulfonates, (fatty acid) -methyltaurides, (fatty acid) -sarcosinates, sulforicinoleates, acylglutamates and mixtures thereof. The anionic surfactants (and mixtures thereof) can be used in the form of their water-soluble or water-dispersible salts, examples being the sodium, potassium, magnesium, ammonium, monohydrate or potassium salts. , di-, and triethanolammonium, and analogous alkylammonium. In at least one embodiment, the anionic surfactant is the salt of an anionic surfactant comprising 12 to 14 carbon atoms. In at least one embodiment, the anionic surfactant is selected from the group consisting of sodium lauryl sulphate, sodium laureth sulphate, sodium tridecyl sulphate, sodium trideceth sulphate, sodium myristyl sulphate, myreth- sodium sulphate and mixtures thereof. Representative anionic surfactants for use in the compositions of the invention include sodium oleylsuccinate, ammonium laurylsulfosuccinate, sodium laurylsulfate, sodium lauryl ether sulfate, sodium lauryl ether sulfosuccinate, ammonium laurylsulfate, ammonium lauryl ether sulphate, sodium dodecyl benzene sulphonate, triethanolamine dodecyl benzene sulphonate, sodium cocoyl isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate. The preferred anionic surfactants are chosen from sodium lauryl sulphate and sodium lauryl ether sulphate (n) OE, (where n is from 1 to 3); more particularly, sodium lauryl ether sulphate (n) OE, (where n is from 1 to 3); especially, sodium lauryl ether sulfate (n) OE where n = 1. Preferably the amount of the alkyl ether sulfate is from 0.5% by weight to 25% by weight of the total composition, more preferably from 3% by weight to 18% by weight, most preferably from 6% by weight to 15% by weight. by weight of the total composition.

The total amount of the anionic surfactant in the compositions of the invention may be in the range of 0.5 wt% to 45 wt%, more preferably 1.5 wt% to 20 wt%. The compositions of the invention may comprise (fatty acyl) isethionate, if present preferably in an amount of 1 to 10% by weight, more preferably 2 to 8% by weight, most preferably 2 to 8% by weight. 5 to 7.5% by weight. A preferred (fatty acyl) isethionate product comprises a surfactant (fatty acyl) -ethionate in an amount of 40 to 80% by weight based on the product, as well as the free fatty acid and / or a fatty acid salt thereof. a quantity of 15 to 50%.

Preferably, more than 20% by weight and less than 45% by weight, more particularly more than 25% by weight and less than 45% by weight of the (fatty acyl) -ethionate have a higher chain length or equal to C16; and more than 50% by weight, preferably more than 60% by weight of the free fatty acid / soap have a C16 to C20 chain length.

In addition, the product may contain isethionate salts, which are usually present in amounts of less than 5% by weight, and traces (less than 2% by weight) of other impurities.

Preferably, a mixture of aliphatic fatty acids is used for the preparation of commercial surfactants (fatty acyl) -ethionates. The surfactants (fatty acyl) -ethionate obtained (ie resulting from a reaction of the isethionate of an alkali metal and an aliphatic fatty acid) should preferably have more than 20% by weight, preferably more than 25% by weight but not more than 45% by weight, preferably 35% (based on the reaction product of (fatty acyl) isethionates) of the fatty acyl group having 16 or more carbon atoms, for give an excellent foam and softness of the product (fatty acyl) -ethionate obtained. These longer chain (fatty acyl) -ethionate surfactants, and fatty acids, for example the fatty acyl group and a fatty acid having 16 or more carbon atoms, can usually form insoluble surfactant / fatty acid crystals in the water at ambient temperatures.

In at least one embodiment, the composition comprises an acylglycinate surfactant. In at least one embodiment, the acylglycinate surfactant satisfies formula (Y):

wherein R1a is a straight or branched chain saturated alkanoyl group having 6 to 30, preferably 8 to 22, particularly preferably 8 to 18 carbon atoms, or is a straight chain mono- or polyunsaturated alkenoyl group; branched, having 6 to 30, preferably 8 to 22 and particularly preferably 12 to 18 carbon atoms, and Qa + is a cation.

In at least one embodiment, Qa + is selected from the group consisting of Li +, Na +, K +, Mg ++, Ca ++, Al +++, NH4 +, a monoalkylammonium ion, a dialkylammonium ion, a trialkylammonium ion and a tetraalkylammonium ion, or combinations of them. Optionally, the radicals R1a are, independently of one another, C1-C22 alkyl radicals or C2-C10 hydroxyalkyl radicals. In at least one embodiment, the acylglycinate surfactant is selected from sodium cocoylglycinate and potassium cocoylglycinate. In at least one embodiment, the acylglycinate surfactant is selected from those of formula (Y) wherein R is C12 alkyl or C14 alkyl. In at least one embodiment, the acyl glycinate surfactant is selected from those of formula (Y) wherein R is C16 alkyl or C18 alkyl.

In at least one embodiment, the composition comprises from 0.01% by weight to 30% by weight, or 1% by weight to 25% by weight, preferably from 5% by weight to 20% by weight, more particularly from 12% by weight to 18% by weight of an anionic surfactant.

In at least one embodiment, the composition comprises a glutamate surfactant of formula (Z), or a salt thereof:

wherein R 'is HOOC-CH2-CH2- or M + -OOC-CH2-CH2-, where M + is a cation; and wherein R is a saturated straight chain or branched alkanoyl group having 6 to 30, preferably 8 to 22, more preferably 8 to 18 carbon atoms, or is a straight or branched chain mono- or polyunsaturated alkenoyl group, having 6 to 30, preferably 8 to 22 and more particularly 12 to 18 carbon atoms. In at least one embodiment, M + is a metal cation. In at least one embodiment, M + is selected from the group consisting of Li +, Na +, K +, Mg ++, Ca ++, Al +++, NH /, a monoalkylammonium ion, a dialkylammonium ion, a trialkylammonium ion and a tetraalkylammonium ion, or combinations thereof. of these. In at least one embodiment, the glutamate surfactant is selected from sodium cocoyl glutamate and potassium cocoyl glutamate. In at least one embodiment, the glutamate surfactant is selected from those of formula (Z), wherein R is a C12 alkyl or C14 alkyl group. In at least one embodiment, the glutamate surfactant is selected from those of formula (Z) wherein R is C16 alkyl or C18 alkyl.

In at least one embodiment, the composition comprises a nonionic surfactant. The nonionic surfactants may be present in an amount in the range of 0 to 5% by weight. Nonionic surfactants that can be incorporated into the compositions of the invention include condensation products of straight or branched chain primary or secondary aliphatic alcohols or phenols with alkylene oxides, usually ethylene oxide. and generally having from 6 to 30 ethylene oxide groups. Particularly preferred are alkyl ethoxylates. Most preferred are alkyl ethoxylates having the formula R - (OCH 2 CH 2) n OH, wherein R is a C 12 -C 15 alkyl chain, and n is 5 to 9. Other suitable nonionic surfactants include mono- or dialkylalkanolamides. Examples include coco-mono- or di-ethanolamide, and coco mono-isopropanolamide. Other nonionic surfactants that can be incorporated in the compositions of the invention are alkylpolyglycosides (APG). Typically, APG is such a surfactant that includes a connected alkyl group (optionally via a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the following formula: RO- (G) n, wherein R is a straight or branched chain alkyl group, which may be saturated or unsaturated, and G is a saccharide group. R can represent an alkyl chain having an average length of about C5 to about C20. Preferably, R represents an alkyl chain having an average length of about C9 to about C12. G may be selected from C5 or C6 monosaccharide residues and is preferably a glucoside. G may be selected from the group consisting of glucose, xylose, lactose, fructose, mannose and derivatives thereof. Preferably, G is glucose. The degree of polymerization, n, can range from about 1 to about 10, or more. More specifically, the value of n is from about 1.3 to about 1.5. Alkylpolyglycosides suitable for use in the invention are commercially available and include, for example, the products identified as Seppic's Oramix NS10; Plantaren 1200 and Plantaren 2000, Henkel. Other nonionic surfactants derived from sugars, which may be incorporated into the compositions of the invention, include fatty acid amides (for example C 10 -C 18) (N-C 1 -C 6 alkyl) -polyhydroxylated amines, such as that C12-C18 N-methylglucamides, as described for example in WO 9 206 154 and US 5 194 639, and N-alkoxy-polyhydroxy fatty acid amides.

In at least one embodiment, the nonionic surfactant has an HLB (hydro-lipophilic ratio) of greater than 12. Optionally, the nonionic surfactant is selected from the group consisting of ethoxylated or ethoxylated / propoxylated fatty alcohols having a fatty chain comprising from 12 to 22 carbon atoms, ethoxylated sterols such as stearyl or lauryl alcohol (OE-7), PEG-16-soya-sterol or PEG-10-soya-sterol, block copolymers polyoxyethylene-polyoxypropylene (poloxamers) and mixtures thereof.

In at least one embodiment, the nonionic surfactants selected from the group consisting of fatty alcohols, fatty acids, fatty acid glycerides or ethoxylated alkylphenols, particularly adducts of from 2 to 30 moles of ethylene and / or from 1 to 5 moles of propylene oxide on C 8 to C 22 fatty alcohols, on C 12 to C 22 fatty acids or on alkylphenols having 8 to 15 carbon atoms in the alkyl group; and C12 to C22 fatty acid diesters of adducts of 1 to 30 moles of ethylene oxide on glycerol, the adducts of 5 to 60 moles of ethylene oxide on the Castor oil or hydrogenated castor oil, sugar esters of fatty acids, especially sucrose esters and one or two C8 to C22 fatty acids, INCI: Sucrose Cocoate, Sucrose Dilaurate, Sucrose Distearate, Sucrose Laurate, Sucrose Myristate, Sucrose Oleate, Sucrose Palmitate, Sucrose Ricinoleate, Sucrose Stearate , sorbitan esters and one, two or three C8 to C22 fatty acids, and a degree of ethoxylation of 4 to 20, polyglyceryl fatty acid esters, in particular of one, two or more fatty acids C8 to C22 and polyglycerol having preferably 2 to 20 glyceryl units, alkylglucosides, alkyloligoglucosides and alkylpolyglucosides having C8 to C22 alkyl groups, for example decylglucosides or laurylglucoside, and mixtures thereof.

In at least one embodiment, the nonionic surfactant is selected from the group consisting of ethoxylation products of fatty alcohols (alkyl polyethylene glycols), alkyl phenol polyethylene glycols, alkyl mercaptan polyethylene glycols, fatty amine ethoxylation products ( alkylaminopolyethylene glycols), fatty acid ethoxylation products (acylpolyethylene glycols), polypropylene glycol ethoxylation products (Pluronics®), fatty acid alkylolamides (polyethylene glycol fatty acid amides), fatty acid amides N-alkyl-, N-alkoxypolyhydroxy, sucrose esters, sorbitol esters, polyglycol ethers and mixtures thereof.

In at least one embodiment, the composition comprises a N-methyl-N-glucamide fatty surfactant. In at least one embodiment, the N-methyl-N-glucamide fatty surfactant satisfies formula (X):

wherein R is a straight or branched chain alkyl or alkenyl group having from 3 to 30 carbon atoms. In at least one embodiment, R is an alkyl group having 3 to 30 carbon atoms. In at least one embodiment, R is a saturated aliphatic hydrocarbon group, which may have a straight or branched chain and may have from 3 to 20 carbon atoms in the hydrocarbon chain, preferably straight or branched. The term "branched" means that a lower alkyl group, such as a methyl, ethyl or propyl group, is present as a substituent on the straight alkyl chain. In at least one embodiment, R is selected from the group consisting of 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2 propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2- butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2- methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2, 3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl and 1-octadecyl. Suitable N-methyl-N-glucamides fatty surfactants are described in WO 2013/178 700 and EP 0 550 637, which are incorporated herein by reference. In at least one embodiment, the N-methyl-N-glucamide surfactant is selected from those which satisfy formula (X), wherein R is a C12 alkyl or C14 alkyl group. In at least one embodiment, the N-methyl-N-glucamide surfactant is selected from those of formula (X) wherein R is C16 alkyl or C18 alkyl.

In at least one embodiment, the composition comprises from 1% by weight to 20% by weight, more preferably from 2% by weight to 10% by weight, even more preferably from 3% to 7% by weight. by weight of a nonionic surfactant.

An amphoteric or zwitterionic surfactant may be incorporated in the composition in an amount in the range of 0.5 wt% to about 8 wt%, preferably 1 wt% to 4 wt% based on the total composition. .

In at least one embodiment, the amphoteric surfactants are selected from the group consisting of N- (C12-C18) alkyl-p-aminopropionates and N- (C12-C18) alkyl-p-iminodipropionates in the form of alkali metal salts or salts of mono-, di- or trialkylammonium; N-acylaminoalkyl-N, N-dimethylacetobetaines, preferably N- (acyl) acylaminopropyl-N, N-dimethylacetobetaines, (C 12 -C 18) alkyl dimethylsulfopropylbetaines, imidazoline-based amphotoisioactives (trade name: Miranol). ®, Steinapon®), preferably the sodium salt of 1- (p-carboxymethyloxyethyl) -1- (carboxymethyl) -2-laurylimidazolinium, the amine oxides, for example the oxides of (C12-C18) alkyl dimethylamine , (fatty acid) -amidoalkyldimethylamine oxides, and mixtures thereof.

In at least one embodiment, the composition comprises a betaine surfactant. Optionally, the betaine surfactant is selected from (C8-C18) alkyl betaines. In at least one embodiment, the betaine surfactant is selected from the group consisting of cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethylalphacarboxyethylbetaine, cetyldimethylcarboxymethylbetaine, oleyldimethylgammacarboxypropylbetaine and laurylbis (2-hydroxypropyl) alphacarboxyethylbetaine and combinations thereof. Optionally, the betaine surfactant is selected from C8 to C18 sulfobetaines. In at least one embodiment, the betaine surfactant is selected from the group consisting of cocodimethylsulfopropylbetaine, stearyldimethylsulfopropylbetaine, lauryldimethylsulfoethylbetaine, laurylbis (2-hydroxyethyl) sulfopropylbetaine and combinations thereof. Optionally, the betaine surfactant is chosen from carboxylated derivatives of imidazole, (C8-C18) alkyl dimethylammonium acetates, (C8-C18) alkyl dimethylcarbonylmethylammonium salts and (C8) fatty acid alkyls. C18) aminobetaines, and mixtures thereof. Optionally, (C8-C18 fatty acid alkyl) aminobetaine is selected from coconut oil derived fatty acid amido-betaine, N- (coconut oil derived fatty acid) -amidoethyl N- [2- (carboxymethoxy) ethyl] glycerol (CTFA name: Cocoamphocarboxyglycinate), and mixtures thereof. A particularly preferred amphoteric or zwitterionic surfactant is cocoamidopropylbetaine. Also suitable are mixtures of any one or more of the amphoteric or zwitterionic surfactants above. The preferred mixtures are those of cocoamidopropylbetaine, with other amphoteric or zwitterionic surfactants as described above. Another preferred amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.

In at least one embodiment, the composition comprises from 0.5% by weight to 20% by weight, preferably from 1% by weight to 10% by weight of an amphoteric surfactant.

In at least one embodiment, the composition comprises a surfactant system. In at least one embodiment, the surfactant system comprises at least one surfactant selected from the group consisting of lauryl sulfate, laureth sulfate, cocoamidopropyl betaine, sodium cocoyl glutamate, lauroamphoacetate, and mixtures thereof. In at least one embodiment, the surfactant system comprises sodium laureth sulphate, sodium lauryl sulphate and optionally cocoamidopropyl betaine. In at least one embodiment, the surfactant system comprises sodium laureth sulfate, potassium cocoylglutamate and cocoamidopropylbetaine.

The lubricants that can be used are, for example, the fatty alcohol components having from 6 to 18 carbon atoms. The other surfactants may be chosen, for example, from non-polymeric cationic quaternary ammonium compounds, in particular cetrimonium chloride (CTAC).

Typical cationic conditioning agents that may be used include cationic quaternary ammonium salts. Examples of such quaternary ammonium salts include benzyltriethylammonium chloride, cetyltrimethylammonium chloride (cetrimonium chloride, CTAC), behentrimonium chloride (BTAC) and cetylpyridinium chloride.

As cationic components, a variety of other cationic polymers may be used, including quaternized cellulose ethers, vinylpyrrolidone copolymers, acrylic polymers, including homopolymers of dimethyldiallylammonium chloride and acrylamide. Also suitable are various types of homo- or copolymers derived from acrylic or methacrylic acid, acrylamide, methylacrylamide, diacetone-acrylamide.

Typical gloss agents are silicones. Non-ionic, volatile or non-volatile silicone fluids, silicone resins and semi-solids or silicone solids are suitable as silicones. The volatile silicones are linear or cyclic silicones having a measurable vapor pressure, which is defined by a vapor pressure of at least 2 mm Hg at 20 ° C. Non-volatile silicone fluids which are insoluble in water are also suitable, including polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, polyether siloxane copolymers, amine-functional silicones and mixtures thereof.

Preferably, the compositions of the present invention contain, as an additional component, a silicone compound. The composition may comprise up to 5% (for example 0.1 to 5%) by weight of a silicone compound. Suitable silicone compounds include polyalkyl or polyaryl siloxanes. The preferred silicone compounds are polydimethylsiloxane, polydiethylsiloxane and polymethylphenylsiloxane, for example available from Wacker (Germany) or Dow Corning, such as Xiameter PMX DC 200. The silicone compounds may be available in the form of oils or emulsions of silicone. The silicone compounds may also be incorporated in the composition of the present invention in the form of an emulsion, the emulsion being prefabricated and added to the formulation, or manufactured during the formulation operation by mechanical mixing with or without the aid. an additional surfactant selected from anionic surfactants, nonionic surfactants, cationic surfactants and mixtures thereof.

The compositions of the invention contain silicone conditioning agents, preferably the latter are emulsified droplets of a silicone conditioning agent, to enhance the conditioning performance.

Suitable silicones include polydiorganosiloxanes, especially polydimethylsiloxanes having the CTFA designation dimethicone. Also suitable for use in the compositions of the invention (especially shampoos and conditioners) are polydimethylsiloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Also suitable for use in the compositions of the invention are silicone gums having a low degree of crosslinking, such as those described for example in WO 96/31188. The viscosity of the emulsified silicone itself (not the The emulsion or the final hair conditioning composition) is usually at least 10,000 cSt at 25 ° C, the viscosity of the silicone itself is preferably at least 60,000 cSt, most preferably at least 500 cSt. 000 cSt, ideally at least 1,000,000 cSt. Preferably, to facilitate formulation, the viscosity does not exceed 109 cSt. The emulsified silicones for use in the shampoo compositions of the invention will usually have an average silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10, ideally 0.01. at 1 pm. Silicone emulsions having an average silicone droplet size of less than 0.15 μm are generally referred to as microemulsions.

The particle size of the silicone particles can be measured by means of a laser light scattering technique, for example using a Malvern Instruments Partizer Sizer2600D. Examples of pre-formed emulsions that may be used include Xiameter MEM 1785 and Microemulsion DC2-1865, available from Dow Corning. These are emulsions / microemulsions of dimethiconol. Crosslinked silicone gums are likewise available in a pre-emulsified form, which is advantageous for facilitating formulation. Another preferred class of silicones for incorporation into the shampoos and conditioners of the invention includes amino functional silicones. By "amino-functional silicone" is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group. Examples of amino functional silicones that may be used include polysiloxanes having the CTFA designation "amodimethicone".

Specific examples of amino functional silicones that can be used in the invention are aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all from Dow Corning). Suitable quaternary silicone polymers are described in EP-A-0 530 974. A preferred quaternary silicone polymer is K3474 from Goldschmidt.

Also suitable are emulsions of amino-functional silicone oils with a nonionic and / or cationic surfactant. Pre-formed emulsions of an amino-functional silicone are likewise available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include cationic emulsion DC939 and nonionic emulsions DC2-7224, DC2-8487, DC2-8177 and DC2-8154 (all from Dow Corning). It is also possible to use a combination of amino-functional and non-amino-functional silicones. The total amount of silicone is preferably from 0.01% by weight to 10% by weight based on the total composition, more preferably from 0.1% by weight to 5% by weight, most preferably 0.5% by weight. weight at 3% by weight.

Typical oils for use in hair compositions are organic oils, which are often esters. The organic oil component may also include glyceryl esters of fatty acids, or triglycerides, coconut oil, almond oil, apricot kernel oil, avocado, babassu oil, evening primrose oil, camelina oil, grapeseed oil, macadamia oil, corn oil, oil meadowfoam, mink oil, olive oil, palm kernel oil, safflower oil, sesame oil, soybean oil, oil of sunflower, wheat germ oil and camellia oil. Sorbitan esters and glyceryl esters as described above are also suitable as the oil component. The cosmetic composition of the invention may contain from 0.05 to 5%, preferably from 0.5 to 5% by weight of at least one oil component.

The composition of the invention may contain from 0.1 to 10% by weight, preferably from 0.2 to 5% by weight, more particularly from 0.2 to 3% by weight, of at least one modifying agent. rheology, in particular a gelling and thickening agent. Examples are cellulosic thickeners, for example hydroxyethylcellulose, hydroxypropylcellulose and carboxymethylcellulose, guar gum, such as hydroxypropylguar, gums of microbial origin such as xanthan gum and scleroglucan gum, and synthetic thickeners, such as crosslinked homo- and copolymers of acrylic acid and / or acrylamidopropanesulfonic acid. Other rheology modifying agents include fatty acid amides such as coco-diethanolamide and monoethanolamide, and oxyethylenated monoethanolamide of the carboxylic acid-alkyl ether.

Rheology modifiers are also known as structuring materials. Typical structural materials include polymeric materials known as "carbomers", including, for example, cross-linked polyacrylic acid polymers available from Lubrizol Corporation under the trade name Carbopol®. Another class of (meth) acrylic acid polymers are the base swellable emulsion (ASE) polymers. The ASE polymers include, for example, Aculyn® 38 copolymer from Dow. ASE carbomers and polymers belong to a class of materials known as hydrodynamic thickeners. These hydrodynamic thickeners include acidic groups in their polymeric structure which, after deprotonation, form anionic charges which repel each other, causing the polymer chains to expand and entangle. Dilatation and chain entanglement can lead to thickening and slurrying effects by the deprotonated polymers. The properties of these hydrodynamic thickeners are impacted by their molecular weight, their content of acid groups, their degree of crosslinking and the extent of swelling. These thickeners are also known as "space filling" or "volume exclusion" and tend to increase both the viscosity and the yield strength as their concentration increases. In use, hydrodynamic polymers usually give rise to compositions that exhibit shear thinning or non-Newtonian behavior. Another class of (meth) acrylic acid rheology modifying agents are hydrophobically-modifiable (HASE) -based swellable polymers. Like ASE polymers, HASE polymers include acidic groups, the deprotonation of which leads to swelling of the polymer. In addition, the HASE polymers comprise groups, chains or hydrophobic side blocks, which give rise to associative interactions with each other, as well as with other hydrophobic species present in the compositions in which they are used, for example, hydrophobic groups of surfactants, fatty acids, other thickeners and the like. The association creates hydrophobic regions distributed in all the volumes of the network of polymer chains. It can also help enhance the properties of the materials as solubilizing agents. The Aculyn® 22 and Aculyn® 28 copolymers from Dow, and the Lubrizol Corporation's Aqua SF-1® copolymer are among the commonly used HASE materials. U.S. Patent No. 4,529,773 (Witiak et al.) Discloses base-soluble emulsion polymers, activated by neutralization at pH greater than 6.5, and then acidified in the presence of a surfactant. They are described as thickeners useful in acidic compositions. The polymers are formed by the copolymerization of a monomer system which comprises: (1) methacrylic or acrylic acid, (2) a C8-C30 alkyl ester of methacrylic or acrylic acid, or, as such, is more particularly described, a polyethylene glycol hydrocarbyl monoether, (3) a C1-C4 alkyl acrylate or methacrylate, and optionally (4) a small amount of a polyethylenically unsaturated monomer. In general, the shampoo composition according to the present invention is used for topical application to the hair, but treatment of the skin and nails is equally possible. The composition is also suitable for cleaning the hairs of animals, preferably mammalian hairs. In general, the shampoo composition comprises 0.01 to 20% by weight of one or more ammonium salts of oligoesters as described above, in particular of formula (I) relative to the total weight of the composition. . More particularly, the oligoester ammonium salt is added in an amount of from 0.05 to 20%, or from 0.1 to 15%, often from 0.1 to 10% by weight relative to the total weight of the composition.

In the shampoo compositions, the oligoester ammonium salt is added in an amount large enough to achieve at least one desired effect, such as, for example, improved shine, hair disentangling, or reduction of static charges. . Preferably, the shampoo composition comprises one or more oligoester ammonium salts of formula (I) in an amount of 0.1 to 15% by weight relative to the total weight of the composition. All percentages by weight given in the invention are, unless otherwise indicated, based on the total weight of the composition of the present invention.

The shampoo composition of the present invention may also comprise as component (F) a fatty compound. The fatty compound is incorporated in the composition in an amount of 0.1 to 20% by weight, preferably 1.0 to 10% by weight. The fatty compound is selected from the group consisting of fatty alcohols (eg, cetyl alcohol, stearyl alcohol or cetearyl alcohol), fatty acids, fatty alcohol derivatives, fatty acid derivatives, and the like. mixtures thereof.

It is understood that the exposed components may in some cases fall into more than one classification, for example some fatty alcohol derivatives may also be classified as fatty acid derivatives. However, a given classification does not represent a limitation to that particular compound, but is presented as a convenience for classification and nomenclature. Non-limiting examples may be found in the International Cosmetic Ingredient Dictionary and Handbook, Fourteenth Edition (2014), and in the CTFA Cosmetic Ingredient Handbook, Second Edition, 1992. Preferably, the fatty alcohols have from 14 to 30 or 16 at 22 carbon atoms. These fatty acids are saturated and may have a straight or branched chain. Examples of fatty alcohols are cetyl alcohol, stearyl alcohol, behenyl alcohol and mixtures thereof. Preferred fatty acids have 10 to 30 or 12 to 22 carbon atoms. These fatty acids may be saturated and may have a straight or branched chain. Also within the scope of the invention are the salts of these fatty acids. Examples of fatty acids are lauric acid, palmitic acid, stearic acid, behenic acid, sebacic acid and mixtures thereof.

The fatty alcohol derivatives and fatty acid derivatives that can be used in the invention include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, esters of fatty alcohols, esters of fatty acids of compounds having esterifiable hydroxy groups, hydroxy-substituted fatty acids and mixtures thereof. Examples of fatty alcohol derivatives and fatty acid derivatives include methyl stearyl ether; polyoxyethylenated ethers of behenyl alcohol, ethyl stearate, cetyl stearate, cetyl palmitate, stearyl stearate, myristyl myristate, polyoxyethylene cetyl stearate, polyoxyethylene stearyl stearate, polyoxyethylenated lauryl, ethylene glycol monostearate, polyoxyethylenated monostearate, polyoxyethylenated distearate, propylene glycol monostearate, propylene glycol distearate, trimethylolpropane distearate, sorbitan stearate, polyglyceryl stearate, glyceryl monostearate, potassium distearate, glyceryl, glyceryl tristearate and mixtures thereof.

The compositions according to the present invention may also comprise an oily, water-insoluble, non-volatile, disperse conditioning agent. By "insoluble" it is meant that the product is not soluble in water (distilled or equivalent) at a concentration of 0.1% (w / w) at 25 ° C.

Oily or fatty materials that can be used are selected from hydrocarbon oils, fatty esters and mixtures thereof. The straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms. Also suitable are polymeric hydrocarbons of alkenyl monomers such as C2-C6 alkenyl monomers. Specific examples of suitable hydrocarbon oils include: paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane , and mixtures thereof. Branched-chain isomers of these compounds as well as hydrocarbons having a greater chain length can also be used.

The fatty esters that can be used are characterized in that they have at least 10 carbon atoms, and include esters having hydrocarbyl chains derived from acids or fatty alcohols. The monocarboxylic acid esters include esters of alcohols and / or acids of the formula R'COOR, wherein R 'and R are independently alkyl or alkenyl, and the sum of the carbon atoms of R 'and R is at least 10, preferably at least 20. Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.

Particularly preferred fatty esters are the mono-, di- and triglycerides, more particularly the mono-, di- and tri-esters of glycerol and long-chain carboxylic acids, such as C1-C22 carboxylic acids. Preferred materials include cocoa butter, palm stearin, sunflower oil, soybean oil and coconut oil.

The oily or fatty material is preferably present in an amount of 0.05 to 10, preferably 0.2 to 5, more preferably about 0.5 to 3% by weight.

The shampoo compositions of the present invention may, in addition to the oligoester ammonium salt and at least one additional component (F), comprise an aqueous carrier. The amount and species of the aqueous carrier are selected based on compatibility with other components and other desired characteristics of the composition. The carrier comprises water and aqueous solutions of lower alkyl alcohols and polyalcohols. The lower alkyl alcohols that can be used in the invention are monoalcohols having 1 to 6 carbon atoms, often ethanol and / or isopropanol. Polyalcohols that can be used include propylene glycol, hexylene glycol, glycerol and propanediol. Preferably, the aqueous carrier is essentially water. Deionized water is preferably used. It is also possible to use water from natural sources, including minerals, according to the desired characteristics of the cosmetic composition. In general, the cosmetic compositions of the present invention may comprise up to 80%, often up to 95% by weight of water.

The shampoo compositions of the present invention may also comprise as additional component (F) other components that can make the composition cosmetically or aesthetically more acceptable, and to provide additional benefits in use. These other components can generally be used individually in amounts of 0.001% to 5% by weight. A wide range of additional components (F) can be formulated in the present composition. They include other conditioning agents, such as hydrolyzed collagen, vitamin E or panthenol, panthenylethyl ether, hydrolyzed keratin, proteins, plant extracts, nutrients; and emollients such as myristyl ether of PPG-3, hydroxyethyl ether of trimethylolpentanol; hair-fixing polymers, such as amphoteric fixing polymers, cationic fixing polymers, anionic fixing polymers, nonionic fixing polymers, and grafted silicone copolymers; preservatives such as benzyl alcohol, methylparaben, propylparaben and imidazolidinylurea; pH adjusting agents such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, generally such as potassium acetate and sodium chloride; coloring agents; oxidizing agents of hair (discoloration) such as hydrogen peroxide, perborate salts and persulfates; hair reducing agents such as thioglycolates; the perfumes ; and sequestering agents, such as disodium ethylenediaminetetraacetate; agents which arrest and absorb ultraviolet and infrared rays, such as octyl salicylate; and anti-dandruff agents such as zinc-pyrithione and salicylic acid.

In at least one embodiment, the composition comprises an antifungal substance. In at least one embodiment, the antifungal substance is selected from the group consisting of ketoconazole, oxiconazole, bifonazole, butoconazole, cloconazole, clotrimazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sulconazole, tioconazole, fluconazole, itraconazole, terconazole, naftifin and terbinafine, zinc-pyrithione, octopirox and combinations thereof. In at least one embodiment, the composition comprises a total amount of antifungal substance in the composition of 0.1 wt% to 1 wt%. In at least one embodiment, the composition comprises pyridinethione anti-dandruff particles, for example the 1-hydroxy-2-pyridinethione salts are highly preferred particulate antidandruff agents. The concentration of anti-dandruff pyridinethione particles may range from 0.1% to 4% by weight, preferably from 0.1% to 3% by weight, more preferably from 0.3% to 2% by weight. . The preferred pyridinethione salts are those which are formed from heavy metals such as zinc, tin, cadmium, magnesium, aluminum and zirconium, preferably zinc, more particularly the zinc salt of the present invention. 1-hydroxy-2-pyridinethione (known under the name "zinc-pyridinethione" or "ZPT"), more particularly the 1-hydroxy-2-pyridinethione salts in the form of lamellar particles. It is also possible to use salts formed from other cations, such as sodium. Anti-dandruff agents based on pyridinethione are described, for example, in Patent No. 2,809,971; U.S. Patent No. 3,236,733; U.S. Patent No. 3,753,196; U.S. Patent No. 3,761,418; U.S. Patent No. 4,345,080; U.S. Patent No. 4,323,683; U.S. Patent No. 4,379,753; and US Patent No. 4,470,982. It is contemplated that when using ZPT as anti-dandruff particles in the compositions of the invention, the growth or re-growth of the hair can be stimulated or regulated, or the two, or that hair loss may be reduced or inhibited, or that the hair may look thicker or fuller.

Preferably, the salt is present in amounts of 0.1 to 1% by weight based on the total composition, to adjust the viscosity of the product. Preferably, the NaOH is present in amounts of 0.1 to 1% by weight based on the total composition, to adjust the pH of the formulation.

The shampoo composition of the present invention may contain as an additional component (F) a Polysorbate for adjusting the rheology, for example Polysorbate-20, Polysorbate-21, Polysorbate-40, Polysorbate-60 and blends. them. Polysorbate may be present in the composition in amounts of up to 5% (e.g., 0.1-5%) by weight.

The shampoo composition may also contain as an additional component (F) a polypropylene glycol. Polypropylene glycols are those having a weight average molecular weight of 200 to 100,000 g / mol. The polypropylene glycol that can be used in the invention can be soluble in water, or insoluble in water, or can have a limited solubility in water, depending on the degree of polymerization, and depending on whether other fragments are therein. , or not, attached. The desired solubility of polypropylene glycol in water will depend for a large part on the shape of the shampoo composition. The polypropylene glycol may be incorporated in the shampoo composition of the present invention in an amount of up to 10% by weight.

The shampoo composition may also contain as an additional component (F) a low melting point oil selected from the group consisting of hydrocarbons having 10 to 40 carbon atoms; unsaturated fatty alcohols having from 10 to 30 carbon atoms such as oleyl alcohol; unsaturated fatty acids having from about 10 to about 30 carbon atoms; fatty acid derivatives; fatty alcohol derivatives; ester oils such as pentaerythritol ester oils, trimethylol ester oils, citrate ester oils, and glyceryl ester oils; poly [alpha] -olefin oils; and mixtures thereof. The low melting point oils preferred in the invention are selected from the group consisting of ester oils such as pentaerythritol ester oils, trimethylol ester oils, citrate ester oils and glyceryl ester oils; poly [alpha] -olefin oils; and mixtures thereof.

Pentaerythritol ester oils and trimethylol ester oils particularly useful in the invention include pentaerythritol tetraisostearate, pentaerythritol tetraoleate, trimethylolpropane triisostearate, trimethylolpropane trioleate, and mixtures thereof.

Particularly useful glyceryl esters include triisostearin, triolein and trilinoline.

The shampoo composition may also contain as an additional component (F) a cationic polymer. The cationic polymers may be present in the composition of the invention to further enhance the deposition performance.

The cationic polymers that may be used may be homopolymers that are cationically substituted, or may be formed from two or more types of monomers. The weight average molecular weight (Mw) of the polymers will generally be between 100,000 and 2 million g / me. The polymers will have cationic nitrogen groups such as quaternary ammonium or protonated amino groups, or a mixture thereof. If the molecular weight of the polymer is too low, then the conditioning effect is poor. If it is too high, then there may be problems of high extensional viscosity, resulting in a running character of the composition during its payment.

The cationic nitrogen group will generally be present as a substituent on a fraction of the total monomer units of the cationic polymer. Thus, when the polymer is not a homopolymer, it may contain non-cationic spacer monomer units. Polymers of this type are described in the CTFA Cosmetic Ingredient Directory, 3rd edition. The ratio of cationic monomer units to non-cationic monomer units is selected to provide polymers having a cationic charge density within the required range, which is generally 0.2 to 3.0 meq / g. The cationic charge density of the polymer is advantageously determined by the Kjeldahl method as described in the US Pharmacopoeia, concerning the chemical tests for the determination of nitrogen.

Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities, and water-soluble spacer monomers such as (meth) acrylamide, alkyl- and dialkyl- (meth) acrylamides, alkyl (meth) acrylates, vinylcaprolactone and vinylpyrrolidone. The alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol.

The cationic amines may be primary, secondary or tertiary amines, depending on the particular species and the pH of the composition. In general, secondary and tertiary amines, especially tertiary amines, are preferred.

The amine-substituted vinyl monomers and amines can be polymerized to amine form and then converted to ammonium by quaternization.

The cationic polymers may comprise mixtures of monomeric units which are derived from amine and / or quaternary ammonium-substituted monomers and / or compatible spacer monomers.

Suitable cationic polymers include, for example, cationic polymers containing quaternary diallylammonium, for example a homopolymer of dimethyldiallylammonium chloride, and copolymers of acrylamide and dimethyldiallylammonium chloride, designated in the industry (CTFA) respectively under the names Polyquaternium 6 and Polyquatemium 7; amino acid salts of amino-alkyl esters of homo- and copolymers of unsaturated carboxylic acids having 3 to 5 carbon atoms (as described in US Patent 4,009,256); cationic polyacrylamides (as described in WO 95/22 311). Other cationic polymers that can be used include cationic polysaccharide polymers such as cationic cellulose derivatives, cationic starch derivatives and cationic guar gum derivatives.

The cationic polysaccharide polymers which can be used in the compositions of the invention comprise the monomers of formula A-O- [R-N + (R 1) (R 2) (R 3) X '], in which: A is a residual anhydroglucose group, such as an anhydroglucose residue of starch or cellulose. R is an alkylene, oxyalkylene, polyoxyalkylene or hydroxyalkylene group, or a combination thereof. R1, R2 and R3 independently represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl or alkoxyaryl groups, each group containing up to about 18 carbon atoms. The total number of carbon atoms of each cationic moiety (i.e., the sum of the carbon atoms of R1, R2 and R3) is preferably about 20 or less, and X is a counter ion anionic. Another type of cationic cellulose comprises the quaternary ammonium polymer salts of a hydroxyethylcellulose reacted with a lauryldimethylammonium-substituted epoxide, designated in the industry (CTFA) as Polyquaternium 24. These materials are available from Amerchol Corporation for example under the trade name Polymer LM-200. Other suitable cationic polysaccharide polymers include quaternary nitrogen-containing cellulose ethers (e.g. as disclosed in U.S. Patent 3,962,418), and copolymers of etherified starch and cellulose (e.g. described in US Patent 3,958,581).

A particularly suitable type of cationic polysaccharide polymer that can be used is a cationic derivative of guar gum, such as guar-hydroxypropyltrimethylammonium chloride (commercially available from Rhodia in its JAGUAR trademark series). Examples of these materials are JAGUAR C13S, JAGUAR C14, JAGUAR C15, JAGUAR C17 and JAGUAR C16, Jaguar CHT and JAGUAR C162.

Mixtures of any one or more of the cationic polymers above may be used.

The cationic polymer may be present in a shampoo composition of the invention in amounts of from 0.01 to 5%, preferably from 0.05 to 1%, more preferably from 0.08 to 0.5% by total weight. of the cationic polymer, relative to the total weight of the composition.

In at least one embodiment, the cationic polymers have a number average molecular weight of at least about 5,000, usually 10,000 to 10 million (g / mol), and are selected from the group consisting of: vinyl monomers having cationic quaternary amine or ammonium functionalities and water-soluble spacer monomers such as acrylamide, methacrylamide, alkyl- and dialkyl-acrylamides, alkyl- and dialkylmethacrylamides, alkyl acrylates alkyl methacrylates, vinylcaprolactone and vinylpyrrolidone. Other suitable spacer monomers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol. Preferred cationic polymers are cationic celluloses, cationic starches and cationic guar gums. Commercially available cationic guar polymers are, for example, Jaguar® from Rhodia or Solvay.

In at least one embodiment, the composition comprises a preservative or a preservative system. Examples of suitable preservatives include benzyl alcohol, piroctone-olamine, phenoxyethanol, parabens, pentanediol, benzoic acid / sodium benzoate, sorbic acid / potassium sorbate, and other organic acids used. to provide antimicrobial protection. Preservative ingredients include anisic acid, lactic acid, sorbitan caprylate, ethylhexylglycerol, caprylylglycol, octanediol, and the like. In at least one embodiment, the composition comprises 0.01 to 5% by weight, particularly preferably 0.05% by weight to 1% by weight of at least one preservative. Suitable preservatives are the substances listed in the International Cosmetic Ingredient Dictionary and Handbook, 9th edition, with the function "preservatives". In at least one embodiment, the preservative is selected from the group consisting of phenoxyethanol, benzylparaben, butylparaben, ethylparaben, isobutylparaben, isopropylparaben, methylparaben, propylparaben, iodopropynyl butylcarbamate, methyldibromoglutaronitrile, DMDM-hydantoin and combinations thereof. In at least one embodiment, the composition comprises a preservative selected from the group consisting of cetyltrimethylammonium chloride, cetylpyridinium chloride, benzethonium chloride, diisobutylethoxyethyldimethylbenzylammonium chloride, sodium N-lauryl sarcosinate, N- sodium palmethylsarcosinate, lauroylsarcosine, N-myristoylglycine, N-laurylsarcosine potassium, trimethylammonium chloride, sodium aluminum chlorohydroxylactate, triethyl citrate, tricetylmethylammonium chloride, 2,4,4'- trichloro-2'-hydroxydiphenyl ether (Triclosan), phenoxyethanol, 1,5-pentanediol, 1,6-hexanediol, 3,4,4'-trichlorocarbanilide (Triclocarban), diaminoalkylamides, L-hexadecylamide; lysine, citrate salts of heavy metals, salicylates, piroctose, zinc salts, pyrithione and its salts of heavy metals, zinc pyrithione, zinc sulphate-phenol, farnesol , ketoconazole, oxiconazol, bifonazole, butoconazole, cloconazole, clotrimazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sulconazole, tioconazole, fluconazole, itraconazole , terconazole, naftifin, terbinafine, selenium disulfide, Octopirox®, methylchloroisothiazolinone, methylisothiazolinone, methyldibromoglutaronitrile, AgCl, chloroxylenol, sodium salts of diethylhexylsulfosuccinate, sodium benzoate, phenoxyethanol, benzyl alcohol, phenoxyisopropanol, parabens, such as butyl-, ethyl-, methyl- and propylparaben and their salts, pentanediol, 1,2-octanediol, ethylhexylglycerol, benzyl alcohol, sorbic acid, benzoic acid, lactic acid, imidazolidinylurea, diazolidinylurea, dimethyloldimethylhydantoin (DMDMH), sodium hydroxymethylglycinate salts, hydroxyethylglycine of sorbic acid and the combinations of these. In at least one embodiment, the preservative is selected from the group consisting of phenoxyethanol, benzylparaben, butylparaben, ethylparaben, isobutylparaben, isopropylparaben, methylparaben, propylparaben, iodopropynyl butylcarbamate, methyldibromoglutaronitrile, DMDM-hydantoin and combinations thereof. In at least one embodiment, the composition is substantially free of parabens.

The shampoo compositions of the present invention may be in the form of rinsing-off products or "dry shampoo" products, they may be opaque or transparent and may be formulated in a wide variety of product forms, including creams, gels, emulsions, mousses and sprays. Preferably, the hair cleaning composition of the present invention is in the form of a rinse-off product.

In at least one embodiment, the shampoo composition is silicone free.

In at least one embodiment, the shampoo composition is sulfate free.

In at least one embodiment, the shampoo composition comprises: (i) from 0.2 wt% to 2.0 wt% of one or more oligoester ammonium salts (OAS) as described in the invention; (ii) from 5% by weight to 20% by weight of one or more anionic surfactants, the composition comprising at least one alkyl sulphate or alkyl ether sulphate; (iii) at least 50% by weight of water; and (iv) at least one cosmetically acceptable additional component (F) selected from the group consisting of silicones, cationic polymers, rheology modifying agents and amphoteric or zwitterionic surfactants.

A preferred embodiment of the shampoo composition relates to a shampoo composition comprising: (i) from 0.2 wt% to 2.0 wt% of one or more oligoester ammonium salts (OAS) such as described in the invention; (ii) from 5% by weight to 20% by weight of one or more anionic surfactants, the composition comprising at least one alkyl sulphate or alkyl ether sulphate; (iii) at least 50% by weight of water; and (iv) at least one additional component selected from the group consisting of silicones, cationic polymers, rheology modifying agents and amphoteric or zwitterionic surfactants; (v) at least one cosmetically acceptable additional component (F).

A preferred embodiment of the shampoo composition relates to a shampoo composition consisting of: (i) from 0.2 wt% to 2.0 wt% of one or more oligoester ammonium salts (OAS) as described in the invention; (ii) from 5% by weight to 20% by weight of one or more anionic surfactants, the composition comprising at least one alkyl sulphate or alkyl ether sulphate; (iii) at least 50% by weight of water; and (iv) at least one additional component selected from the group consisting of silicones, cationic polymers, rheology modifiers, and amphoteric or zwitterionic surfactants; (v) at least one additional cosmetically acceptable component (F) selected from the group consisting of conditioning agents such as hydrolyzed collagen, vitamin E, or panthenol, panthenyl ethyl ether, hydrolyzed keratin, proteins, plant extracts , nutrients ; and emollients such as myristyl ether of PPG-3, hydroxyethyl ether of trimethylpentanol; hair-fixing polymers such as amphoteric fixing polymers, cationic fixing polymers, anionic fixing polymers, nonionic fixing polymers and silicone graft copolymers; preservatives, such as benzyl alcohol, methylparaben, propylparaben and imidazolidinylurea; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, generally such as potassium acetate and sodium chloride; coloring agents; hair oxidation agents (discoloration), such as hydrogen peroxide, perborate salts and persulfates; hair reducing agents such as thioglycolates; the perfumes ; and sequestering agents such as disodium ethylenediaminetetraacetate; ultraviolet and infrared radiation arresting and absorbing agents such as octyl salicylate; and anti-dandruff agents such as zinc-pyrithione and salicylic acid.

The third aspect of the present invention relates to the use of the ammonium salt of oligoester as described, in particular of formula (I) as defined above, as an ingredient in a composition of shampoo, preferably as a surfactant in a shampoo composition.

The fourth aspect is a process for preparing the shampoo composition, comprising the step of mixing at least one oligoester ammonium salt, in particular of formula (I) as defined above, and of at least one additional component (F) as defined above.

The shampoo compositions may be prepared by any conventional method well known in the art. For example, they may be prepared by a hot or cold process, preferably a cold process (without external heating), by adding the ingredients of the composition to the aqueous phase, or by combining two or more phases (aqueous and / or oily) after stirring. The order of addition of ingredients depends on the ingredients used, and so is the neutralization sequence and pH adjustment. Individual ingredients may need to be added in molten form from a heated container if they are solid at room temperature and are not readily soluble in water. The ammonium salts of oligoester (optionally, purified) and one or more additional components (F) are introduced by mixing in deionized water (heated or at room temperature). Additional ingredients are added, and the temperature is adjusted to ensure their best solubility until the components are homogenized, and no solid is observed.

The fifth aspect relates to a hair treatment method, comprising: a) applying, on wet hair, the shampoo composition as defined above, then b) removing the shampoo composition from the hair .

In at least one embodiment of the fifth aspect of the present invention, the hair treatment method comprises: (a) applying the shampoo composition to the hair; then (b) washing the hair with the shampoo composition; then (c) removing the shampoo composition from the hair; then (d) optionally, applying a conditioning composition to the wet hair; then the elimination of the conditioning composition of the hair, or optionally the application of a conditioner without rinsing (leave on) on wet or dry hair.

In at least one embodiment of the fifth aspect, the conditioner composition comprises at least one oligoester ammonium salt (OAS) of formula (I) and at least one cosmetically acceptable additional component (F).

wherein: R1 is a straight or branched chain C12-C24 alkyl group or a straight or branched chain C12-C24 alkenyl group; R2 is a straight or branched chain C1-C8 alkylene group or a straight or branched chain C2-C8 alkenylene group; A is at least one independently selected from (C1-C6) alkylene-C1-C6-C6-C6-alkylene-satisfying compounds, wherein R5 and R6 are each independently selected from the group consisting of H, OH, C1-C6 alkyl and hydroxy-C1-C6 alkyl; and is at least once independently selected from quaternary ammonium compounds of formula (II)

wherein R 3, R 4 are each independently a straight or branched chain C 1-6 alkyl group or a straight or branched chain hydroxy (C 1-6 alkyl) group; n is an integer of 1 to 30, preferably 1 to 10; and m is an integer of 1 to 31, preferably 1 to 10, describing the charge; [(Xp ") i / p] is a counterion selected from the group consisting of monovalent anions having the formula [X '], divalent anions having the formula [(X2') o, s] and trivalent anions having the formula [(X3 ') i / 3] ·

The hair treatment method according to the present invention may also include one or more additional steps using commonly known compounds such as, for example, a color-altering composition, a developer composition, a pretreatment composition and / or a post-treatment composition. These commonly known compositions include well known conventional additives which are usually applied in hair treatment compositions, such as coloring agents, alkalinity agents and acidifying agents, buffers, thickeners, gelling agents, rheological modifiers, antioxidants, perfumes and chelating agents.

The preparation of the oligoester ammonium salt of general formula (I) can be carried out by methods known to those skilled in the art, for example by (i) first, contacting the components of a reaction mixture (a) to (d), in the presence of a high temperature at 80 to 220 ° C, in particular at 150 to 210 ° C, with continuous removal of the water of reaction; 0.5 to 3.0 mole equivalents, often 0.75 to 3.0 mole equivalents, of a diethanolamine compound represented by the formula (a)

wherein R3 is straight or branched chain C1-C6 alkyl, preferably straight or branched C1-C4 alkyl, and more preferably methyl or ethyl; 0.5 to 1.5 mole equivalents of a dicarboxylic acid represented by the formula (b)

wherein R2 is a straight or branched chain C1-C10 alkylene group, or a straight or branched chain C2-C10 alkenylene group, preferably a C2-C8 alkylene group, and is more particularly a C4 alkylene group; ; 0.5 to 1.5 mole equivalents of an organic triol represented by formula (c1) or (c2)

where R4 is a hydrogen atom or a straight or branched chain C1-C4 alkyl group or a hydroxyl (C1-C4) alkyl group, and is preferably a hydrogen atom, the methyl or ethyl group, more particularly, R4 is a hydrogen atom; 1.0 mole equivalent of a monocarboxylic acid represented by the formula (d) R1-COOH (d) wherein R1 is a straight or branched chain C12-C24 alkyl group or a chain C12-C24 alkenyl group straight or branched, preferably a straight or branched chain C 12 -C 22 alkyl group or a straight or branched chain C 12 -C 22 alkenyl group, preferably is a C 20 -C 22 alkyl group; (ii) reacting the oligoester product of step (i) with a quaternizing agent (e), preferably from the group of commonly known alkylating agents such as dimethyl sulfate, diethyl sulfate and sodium halides; alkyl; then (iii) optionally, removing and purifying the oligoester ammonium salt (s).

The alkylating agents which can be used are, for example, dimethyl sulphate, diethyl sulphate, dimethyl carbonate, diethyl carbonate, and alkyl halides, such as methyl chloride or ethyl chloride. methyl bromide, ethyl bromide, methyl iodide or ethyl iodide. The contacting step is carried out under conditions sufficient to produce the oligoester amine, where n is an integer of 1 to about 30. The components of the reaction mixture may be contacted successively or simultaneously. Preferably component (a), said dicarboxylic acid (b), said polyol (c) and said monocarboxylic acid (d) are contacted in the molar ratios described. Preferably, the contacting is carried out in the presence of an esterification catalyst such as a catalyst based on a Brönstedt or Lewis acid, or a metal catalyst. Examples are hypophosphorous acid, p-toluenesulfonic acid, titanium tetrabutylate or Fascat®. The invention also relates to a multi-part kit of compositions for cleaning hair and conditioning hair. The term "kit" encompasses elements that are either solid or packaged together. The multi-part kit can be distributed to end-users through hair salons, but one aspect of the invention involves distributing the kits to consumers through retail channels such as drug stores, drugstores stores selling cosmetics and online stores. The kit includes separate compartments, containing formulations for shampoo and conditioning treatment. The term "compartment" refers to any receptacle, regardless of its shape, material or closure system, which serves to contain. The term encompasses the interior of a tube, bag, can, bowl, bottle, package, envelope or other container. The components of the multipart kit may be contained in a single receptacle, or may be subdivided into multiple receptacles. The multi-part kit may further include a compartment containing a hair coloring composition and / or a composition for moisturizing and maintaining the quality of the treated hair.

For discolored or colored hair, additional compartments in the multi-part kit are advantageous. There is a high need for an easy-to-use hair and hair conditioning kit that provides a specialized skincare plan for the consumer to maintain hair condition. The invention provides all this in a multi-part kit, with all the components necessary for maintaining the condition of the hair for several weeks. The kit may include at least one compartment containing a pretreatment composition. The invention is illustrated in more detail by the nonlimiting examples below.

Example 1 Preparation of an Oligoester Precursor Nitrogen was introduced into a 2-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, 119.2 g (1.0 g). mol) of methyldiethanolamine (component (a)), 510.9 g (1.5 mol) of behenic acid (component (d)), 219.2 g (1.5 mol) of adipic acid (component (b) )) and 138.16 g (1.5 mol) of glycerol (component (c)). The reaction mixture is heated to 160 ° C. and the distillation of the reaction water is started. The temperature is raised to 206 ° C when the head temperature decreases. The reaction water is continuously removed from the reaction mixture by distillation at 160-206 ° C over a period of 5 hours.

The product (782 g) is obtained in the form of a clear brown liquid (acid number 10.2 mg KOH / g, low N: 1.50%, Mn = 1246 g / mol, Mw = 1354 g / mol).

Example 2: Oligoester Ammonium Salt

150.0 g of the oligoester of Example 1 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 85 ° C. C. 10.1 g (0.08 mol, 0.5 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 15 minutes. The reaction mixture is stirred for 5 hours at 90 ° C. The product (151 g) is obtained in the form of a light brown solid (N, N: 0.70%).

Example 3: Oligoester Ammonium Salt

150.0 g of the oligoester of Example 1 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 85 ° C. C. 19.9 g (0.15 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 15 minutes.

The reaction mixture is heated for 5 hours at 90 ° C. The product (154 g) is obtained as a light brown solid (N, N: 0.11%).

Example 4 Preparation of an Oligoester Precursor

119.2 g (1.0 mol) of methyldiethanolamine, 510.9 g (1.5 mol) of behenic acid, 219.2 g (1.5 mol) of adipic acid are introduced under nitrogen atmosphere and 223.8 g (1.5 mol) of triethanolamine in a 2-liter flask equipped with stirrer, distillation apparatus and thermometer. The reaction mixture is heated at 160 ° C for 3 hours, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 200 ° -205 ° C. for 8 hours, and the reaction water is distilled off from the reaction mixture. The product (963 g) is obtained as a brown wax (acid number: 1.7 mg KOH / g, N-bottom: 3.49%, Mn = 1756 g / mol, Mw = 2 139 g / mol).

Example 5: Oligoester Ammonium Salt

300.0 g of the oligoester of Example 4 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 85 ° C. C. 92.2 g (0.73 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 20 minutes. During the addition, the product mixture obtained becomes highly viscous, and 98.1 g of butyldiglycol is added. The reaction mixture is stirred for 5 hours at 85 ° C. The product (400 g, 80% active content) is obtained in the form of a brown wax (N, N: 0.01%).

Example 6: Oligoester Ammonium Salt

330.0 g of the oligoester of Example 4 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with an agitator, a distillation apparatus and a thermometer, and the mixture is heated to 85 ° C. C. 51.8 g (0.41 mol, 0.5 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 20 minutes. During the addition, the resulting product mixture becomes highly viscous, and 42.4 g of butyldiglycol is added. The reaction mixture is stirred for 5 hours at 85 ° C. The product (380 g, 90% active content) is obtained in the form of a brown wax (N, N: 1.31%).

Example 7 Preparation of an Oligoester Precursor

238.4 g (2.0 mol) of methyldiethanolamine, 340.4 g (1.0 mol) of behenic acid, 219.2 g (1.5 mol) of adipic acid are introduced under nitrogen atmosphere and 138.5 g (1.5 mol) of glycerol in a 2 liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 160 ° C for 2 hours, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 200 ° -205 ° C. for 7 hours and the reaction water is distilled off from the reaction mixture. The product (810 g) is obtained in the form of a brown wax (acid number: 3 mg KOH / g, low-N: 2.85%, Mn = 1314 g / mol, Mw = 1445 g / mol). mol).

Example 8: Oligoester Ammonium Salt

260.0 g of the oligoester of Example 7 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 85 ° C. C. 65.3 g (0.52 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 20 minutes. During the addition, the resulting product mixture becomes highly viscous, and 81.3 g of butyldiglycol is added. The reaction mixture is stirred for 5 hours at 85 ° C. The product (370 g, 80% active content) is obtained in the form of a brown wax (Bas-N <0.01%).

Example 9: Oligoester Ammonium Salt

280.0 g of the oligoester of Example 7 are introduced into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer and heated to 85 ° C. under a nitrogen atmosphere. C. 35.9 g (0.29 mol, 0.5 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 20 minutes. During the addition, the product mixture obtained becomes highly viscous, and 35.1 g of butyldiglycol is added. The reaction mixture is stirred for 5 hours at 85 ° C. The product (320 g, 90% active content) is obtained in the form of a brown wax (N, N = 1.04%).

Example 10 Preparation of an Oligoester Precursor

238.4 g (2.0 mol) of methyldiethanolamine, 681.2 g (2.0 mol) of behenic acid, 219.2 g (1.5 mol) of adipic acid are introduced under nitrogen atmosphere and 138.2 g (1.5 mol) of glycerol in a 2 liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 170 ° C for 2 hours, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C. for 1 hour, then at 200 ° C. for 1 hour and then at 210 ° C. for 1 hour. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (1127 g) is obtained in the form of a brown wax (acid number: 2.9 mg KOH / g, N 2: 2.24%, Mn = 1029 g / mol, Mw = 1 329 g / mol).

Example 11: Oligoester Ammonium Salt

255.1 g of the oligoester of Example 10 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with an agitator, a distillation apparatus and a thermometer, and the mixture is heated to 60 ° C. C. 50.4 g (0.40 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 25 minutes. During the addition, the resulting product mixture becomes highly viscous, and 30.1 g of butyldiglycol is added. The reaction mixture is heated to 80 ° C and stirred at this temperature for 0.5 hours. The reaction mixture is then heated to 90 ° C and stirred at this temperature for 4.5 hours. The product (288 g, 90% active content) is obtained as a brown solid (Bas-N <0.01%).

Example 12 Preparation of an Oligoester Precursor

119.2 g (1.0 mol) of a methyldiethanolamine, 340.6 g (1.0 mol) of behenic acid, 219.2 g (1.5 mol) of acid are introduced under a nitrogen atmosphere. adipic acid and 138.2 g (1.5 mol) of glycerol in a 2-liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 170 ° C for 1 hour, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C. for 1 hour, then at 200 ° C. for 1 hour and then at 210 ° C. for 0.5 hour. During the heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (703 g) is obtained in the form of a brown wax (acid number 5.2 mg KOH / g, N-bottom: 1.66%, Mn = 1176 g / mol, Mw = 1610 g). / mol).

Example 13: Oligoester Ammonium Salt

253.0 g of the oligoester of Example 12 are introduced into a 1-liter flask equipped with an agitator, a distillation apparatus and a thermometer and heated to 60 ° under a nitrogen atmosphere. C. 37.3 g (0.29 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 15 minutes. During the addition, the resulting product mixture becomes highly viscous, and 41.2 g of butyldiglycol is added. The reaction mixture was heated to 80 ° C and stirred at that temperature for 1 hour. The temperature is then raised to 90 ° C, and the reaction mixture is stirred at this temperature for a further 4 hours. The product (303 g, 88% active content) is obtained as a brown solid (Nb = 0.02%).

Example 14 Preparation of an Oligoester Precursor

Under a nitrogen atmosphere, 119.2 g (1.0 mol) of methyldiethanolamine, 170.3 g (0.5 mol) of behenic acid, 109.6 g (0.75 mol) of adipic acid and 23.0 g (0.25 mol) of glycerol in a 2-liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 170 ° C for 1 hour, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 180 ° C for 2 hours, then at 190 ° C for 2 hours, then at 200 ° C for 2 hours, and then at 210 ° C for 1 hour. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (343 g) is obtained as a brown solid (acid number: 2.6 mg KOH / g, N-bottom: 3.21%, Mn = 1892 g / mol, Mw = 3038). g / mol).

Example 15: Oligoester Ammonium Salt

150.0 g of the oligoester of Example 14 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer and heated to 60 ° C. C. The mixture is added dropwise over 30 minutes so that the temperature does not exceed 80 ° C (0.30 mole, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate. Due to the high viscosity of the product mixture obtained, 57.5 g of butyldiglycol were added portionwise during the addition of dimethyl sulfate. The temperature is raised to 80 ° C, and the reaction mixture is stirred at this temperature for 1 hour. The temperature is then raised to 90 ° C, and the reaction mixture is stirred at this temperature for a further 4 hours. The product (349 g, 77% active content) is obtained as a brown solid (Bas-N <0.01%).

Example 16 Preparation of an Oligoester Precursor

178.8 g (1.5 mol) of methyldiethanolamine, 170.3 g (0.5 mol) of behenic acid, 109.6 g (0.75 mol) of adipic acid and 69.1 g (0.75 mol) glycerol in a 2 liter flask equipped with stirrer, distillation apparatus and thermometer. The reaction mixture is heated at 170 ° C for 2 hours, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C. for 1.5 hours and then at 200 ° C. for 1 hour. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (391 g) is obtained as a brown solid (acid number: 1.2 mg KOH / g, N-bottom: 2.98%;

Mn = 908 g / mol; Mw = 1360 g / mol).

Example 17: Oligoester ammonium salt

234.7 g of the oligoester of Example 16 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 60 ° C. C. 61.8 g (0.49 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 45 minutes. The addition is stopped three times, and cooled to 70 ° C to avoid reaction temperatures above 80 ° C in the reaction mixture. During the addition, the resulting product mixture becomes highly viscous, and 69.6 g of butyldiglycol are added in portions. The reaction mixture is heated to 90 ° C and stirred at this temperature for 5 hours. The product (349 g, 81% active content) is obtained as a brown solid (Bas-N = 0.06%).

Example 18: Preparation of an oligoester precursor

178.8 g (1.5 mol) of methyldiethanolamine, 170.3 g (0.5 mol) of behenic acid, 109.6 g (0.75 mol) of adipic acid and 46 ml are introduced under a nitrogen atmosphere; 1 g (0.5 mol) of glycerol in a 2 liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 170 ° C for 2 hours, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C. for 1 hour and then at 200 ° C. for 1 hour. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (446 g) is obtained as a brown solid (acid number: 2.9 mg KOH / g, N-bottom: 4.12%, Mw = 985 g / mol).

Example 19: Oligoester Ammonium Salt

237.9 g of the oligoester of Example 18 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 60 ° C. C. 86.5 g (0.69 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 45 minutes. The addition is stopped three times, and cooled to 70 ° C to prevent reaction temperatures above 80 ° C in the reaction mixture. During the addition, the product mixture obtained becomes highly viscous, and 62.3 g of butyldiglycol is added. The reaction mixture is heated to 90 ° C and stirred at this temperature for 5 hours. The product (372 g, 84% active content) is obtained as a brown solid (Bas-N = 0.03%).

Example 20 Preparation of an Oligoester Precursor

178.8 g (1.5 mol) of methyldiethanolamine, 170.3 g (0.5 mol) of behenic acid, 73.1 g (0.5 mol) of adipic acid and 69 are introduced under nitrogen atmosphere, 1 g (0.75 mol) of glycerol in a 2 liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 170 ° C for 1 hour, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C for 2 hours, then at 200 ° C for 1 hour, and then at 210 ° C for 1 hour. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (386 g) is obtained as a brown solid (acid number: 1.1 mg KOH / g, N-bottom: 3.39%, Mn = 768 g / mol, Mw = 1037 g / mol).

Example 21: Oligoester Ammonium Salt

150.0 g of the oligoester of Example 20 are introduced into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and heated to 60 ° C. under a nitrogen atmosphere. C. 44.8 g (0.36 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 30 minutes. During the addition, the resulting product mixture becomes highly viscous, and 41.1 g of butyldiglycol is added. The reaction mixture was heated to 80 ° C and stirred at that temperature for 1 hour. The temperature is then raised to 90 ° C, and the reaction mixture is stirred at this temperature for a further 4 hours. The product (210 g, 83% active content) is obtained as a brown solid (Bas-N not detected).

Example 22 Preparation of an Oligoester Precursor

178.8 g (1.5 mol) of methyldiethanolamine, 170.3 g (0.5 mol) of behenic acid, 36.5 g (0.25 mol) of adipic acid are introduced under nitrogen atmosphere and 69.1 g (0.76 mol) of glycerol in a 2-liter flask equipped with a stirrer, a distillation apparatus and a thermometer. The reaction mixture is heated at 170 ° C for 1 hour, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C. for 2 hours and then at 200 ° C. for 1.5 hours. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (382 g) is obtained in the form of a brown wax (acid number: 2.6 mg KOH / g, low N: 3.39%, Mw = 842 g / mol).

Example 23: Oligoester Ammonium Salt

150.0 g of the oligoester of Example 22 are introduced under a nitrogen atmosphere into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer, and the mixture is heated to 60 ° C. C. 44.8 g (0.36 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 30 minutes. During the addition, the resulting product mixture becomes highly viscous, and 17.5 g of butyldiglycol is added. The reaction mixture was heated to 80 ° C and stirred at that temperature for 1 hour. The temperature is then raised to 90 ° C, and the reaction mixture is stirred at this temperature for a further 4 hours. The product (177 g, 92% active content) is obtained as a brown solid (Bas-N <0.17%).

Example 24: Preparation of an oligoester precursor

178.8 g (1.5 mol) of methyldiethanolamine, 170.3 g (0.5 mol) of behenic acid, 220.8 g (0.75 mol) of sebacic acid are introduced under nitrogen atmosphere and 69.1 g (0.75 mol) glycerol in a 2 liter flask equipped with stirrer, distillation apparatus and thermometer. The reaction mixture is heated at 170 ° C for 1 hour, and the reaction water is distilled off from the reaction mixture. The reaction mixture is then heated at 190 ° C. for 2 hours and then at 200 ° C. for 2 hours. During heating, the reaction water is continuously removed from the reaction mixture by distillation. The product (510 g) is obtained as a brown solid (acid number: 2.6 mg KOH / g, N 2: 2.91%, Mn = 1 405 g / mol, Mw = 2 205 g / mol).

Example 25: Oligoester ammonium salt

150.0 g of the oligoester of Example 24 are introduced into a 1-liter flask equipped with a stirrer, a distillation apparatus and a thermometer and heated to 60 ° under a nitrogen atmosphere. C. 38.6 g (0.31 mol, 0.98 equivalents / nitrogen atom in the oligoester) of dimethyl sulfate are added dropwise over 30 minutes. During the addition, the resulting product mixture becomes highly viscous, and 15.9 g of butyldiglycol is added. The reaction mixture was heated to 80 ° C and stirred at that temperature for 1 hour. The temperature is then raised to 90 ° C, and the reaction mixture is stirred at this temperature for a further 4 hours. The product (182 g, 92% active content) is obtained as a brown solid (Bas-N <0.07%).

Examples 26 to 48: Shampoo compositions

The shampoo compositions of Examples 26 to 48 are prepared by mixing the components as listed below. The shampoo compositions are thick, clear or opaque liquids having similar appearance and physical properties to the commercially available rinse-off shampoo products. The pH of the formulations is adjusted to a value of 4.5 to 6.5. For each ingredient, the INCI name and the active ingredient content in% by weight are indicated.

Example 26: A shampoo composition

Example 27: A shampoo composition

Example 28: A shampoo composition

Example 29: A shampoo composition

Example 30: A shampoo composition

Example 31: A shampoo composition

Example 32: A shampoo composition

Example 33: A shampoo composition

Example 34: A shampoo composition

Example 35: A shampoo composition

Example 36: A shampoo composition

Example 37: A shampoo composition

Example 38: A shampoo composition

Example 39: A shampoo composition

Example 40: A shampoo composition

Example 41: A shampoo composition

Example 42: A shampoo composition

Example 43: A shampoo composition

Example 44: A shampoo composition

Example 45: A shampoo composition

Example 46: A shampoo composition

Example 47: A shampoo composition

Example 48: A shampoo composition

Experimental part

Essay of shampoo compositions

Studies are carried out with locks of hair (by use of Kerling European smooth hair braids, DE, length 15 cm, each hair about 2.6 g). Chemically treated hair (4 times discolored) is used. We tested two products of shampoo: the hair is washed in a commercial silicone-free shampoo (Balea Jeden Tag Shampoo, Cool Blossom), and with this same shampoo to which we added 2% (content in active ingredients) of the material of the Example 5 The locks of hair were prewashed twice in tap water (Frankfurt, Germany) thermostated (37 ° C), with a flow rate of 4 l / min using a 14% solution. % (active ingredient) of sodium laureth sulfate, SLES, in water at pH 5.5, using 0.1 g / g SLES / hair. Then two shampoo washes were done, by applying shampoo, massage and rinsing the hair with water. Wet hair disentangling force was measured on wet wicks using the Diastron (United Kingdom) MTT 175 tester, and the hair was allowed to dry overnight under controlled temperature and temperature conditions. humidity (22 ° C, relative humidity 45%). The next day, the hair shine was measured on the dry locks with the Samba Haïr System (Bossa Nova Tech, CA, USA). The BNT index for hair brilliance is calculated by the Bossa Nova algorithm. For each product, three braids of hair were used, and each was measured three times.

The following results were obtained:

It is apparent that the addition of the OAS of Example 5 greatly improves the ease of disentangling by decreasing the force required for disentangling the hair, which is normally perceived by consumers as a conditioning and repair effect. In addition, the OAS of Example 5 increases hair gloss in a visually perceived way by consumers.

This gives a repaired and healthier hair effect. In addition to the conditioning properties, OAS is expected to bring additional benefits to consumers, such as volume and / or reduction of crimp, conditioned and / or moistened sensation on dry hair, ease styling, etc.

Claims (15)

claims A shampoo composition comprising at least one oligoester ammonium salt (OAS) and at least one additional cosmetically acceptable component (F), wherein the oligoester ammonium salt (OAS) can be obtained by the steps following: (i) heating a mixture of components (a) to (d) below, with continuous removal of the water of reaction: 0.5 to 3.0 mole equivalents of a diethanolamine compound represented by the formula (a) wherein R3 is a straight or branched chain C1-C6 alkyl group, preferably straight or branched chain C1-C4 alkyl, more particularly methyl or ethyl; 0.5 to 1.5 mole equivalents of a dicarboxylic acid represented by the formula (b) wherein R2 is straight or branched chain C1-C10 alkylene or straight or branched chain C2-C10 alkenylene, preferably C2-C8 alkylene, more preferably C4 alkylene; 0.5 to 1.5 mole equivalents of an organic triol represented by formula (c1) or (c2) where R4 is a hydrogen atom or a straight or branched chain C1-C4 alkyl or hydroxyl (C1-C4) alkyl group, preferably a hydrogen atom, the methyl or ethyl group, more particularly an atom hydrogen; 1.0 mole equivalent of a monocarboxylic acid represented by the formula (d) R1-COOH (d) wherein R1 is a straight or branched chain C12-C24 alkyl or straight chain C12-C24 alkenyl group or branched, preferably straight or branched chain C 12 -C 22 alkyl or straight or branched chain C 12 -C 22 alkenyl, more particularly C 20 -C 22 alkyl; (ii) reacting the oligoester product of step (i) with a quaternizing agent (e), in particular the dimethyl sulfate group, diethyl sulfate and alkyl halides; (iii) optionally, isolating and purifying the oligoester ammonium salt (OAS). A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to claim 1, wherein in the diethanolamine component (a), R3 is methyl. A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to claim 1 or 2, wherein the dicarboxylic acid (b) is selected from the group consisting of adipic acid, glutaric acid, succinic acid, sebacic acid, itaconic acid, maleic acid and combinations thereof. A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to any one of claims 1 to 3, wherein the organic triol (c) is selected from the group consisting of glycerol, triethanolamine , and combinations thereof. A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to any one of claims 1 to 4, wherein the carboxylic acid (d) is selected from the group consisting of behenic acid , oleic acid, fatty acid derived from coconut oil, linoleic acid, and combinations thereof. A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to any one of claims 1 to 5, wherein the OAS is preferably prepared by the choice of the molar ratio of the components (a). ), (b), (c) and (d) such that the mole equivalents of the hydroxyl functions are in excess of the mole equivalents of the acid functions. A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to any one of claims 1 to 6, wherein the content of cleaning ingredient is from 1% to 20% based on the total weight of the active ingredient in the composition, preferably 5% to 18%, more particularly 8% to 16%. A shampoo composition comprising at least one oligoester ammonium salt (OAS) according to any one of claims 1 to 7, wherein the cleaning ingredient is selected from the group consisting of non-polymeric surfactants, saponins , polymeric surfactants, and combinations thereof. 9. Shampoo composition comprising at least one oligoester ammonium salt (OAS) of formula (I) and at least one additional cosmetically acceptable component (F) wherein: R1 is a straight or branched chain C12-C24 alkyl group or a straight or branched chain C12-C24 alkenyl group; R2 is a straight or branched chain C1-C8 alkylene group or a straight or branched chain C2-C8 alkenylene group; A is, at least once, independently selected from: (C 1 -C 6) alkylene-C 5 -C 6 -alkylene (C 1 -C 6) alkylene, wherein R 5 and R 6 are each independently selected from the group consisting of OH, (C1-C6) alkyl and hydroxy (C1-C6) alkyl; and is at least once independently selected from quaternary ammonium compounds of formula (II) wherein R3 and R4 are each independently a straight or branched chain C1-C6 alkyl group or a straight or branched chain hydroxy-alkyle-ι-Οβ alkyl group; n is an integer of 1 to 30, preferably 1 to 10; and m is an integer of 1 to 31, preferably 1 to 10, describing the charge; [(Xp) i / p] is a counterion selected from the group consisting of monovalent anions having the formula [X '], divalent anions having the formula [(X2) 0.5] and trivalent anions having the formula [(X3 ') i / 3] · 10. Shampoo composition according to claim 9, characterized in that, in formula (I), A satisfies (C1-C4 alkylene) -CR5R6- (C1-C4 alkylene), where R5 and R6 are each independently selected from the group consisting of H, OH, C1-C2 alkyl and hydroxy-methyl. The shampoo composition according to claim 9 or 10, wherein in the formula (I), A, the group (C 1 -C 6 alkylene) -CR 5 R 6 - (C 1 -C 6) alkylene is: -CH 2 -CH [OH] -CH2-, -CH2-CH [CH2OH] -CH2 -CH2-C [CH3] [CH2OH] -CH2-, -CH2-C [CH2CH3] [CH2OH] -CH2-, and -CH2-C [CH2OH] 2-CH2-, The shampoo composition of any one of claims 1 to 11 comprising: (i) from 0.2 wt% to 2.0 wt% of one or more oligoester ammonium salts (OAS) as described in any one of claims 1 to 11; (ii) from 5% by weight to 20% by weight of one or more anionic surfactants, the composition comprising at least one alkyl sulphate or alkyl ether sulphate; (iii) at least 50% by weight of water; and (iv) at least one additional component selected from the group consisting of silicones, cationic polymers, rheology modifiers, and amphoteric or zwitterionic surfactants. 13. Use of an oligoester ammonium salt (OAS) obtained by a process as defined in any one of claims 1 to 8, or an oligoester ammonium salt (OAS) according to Claims 9 to 11 as a surfactant in a shampoo composition. A process for preparing a shampoo composition according to any one of claims 1 to 12, comprising the step of preparing one or more oligoester ammonium salts (OAS) as described in one of any of claims 1 to 12, and OAS mixtures to one or more additional components (F). A hair treatment method, comprising: a) applying, on wet hair, the shampoo composition according to any one of claims 1 to 12, and then b) removing the hair shampoo composition.