Biodegradable two-phase hair treatment

Abstract

Hair treatment preparations which comprise two superimposed layers and a common interface and contain at least one C9-C12 alkane in the oil phase (II) and at least one cationic phospholipid in the water phase (I) are suitable for hair care, in particular for improving the detanglability, combability, smoothness, shine and frizz of hair.

Description

[0001] Henkel AG & Co. KGaA

[0002] Dr. Ludwig

[0003] Biodegradable two-phase hair treatment

[0004] The application describes hair treatment products with two superimposed layers and a common interface, containing Cg-Ci2-alkan(s) in the oil phase and a cationic phospholipid in the aqueous phase.

[0005] The application further describes the cosmetic use of the hair treatment products for hair care.

[0006] Two-phase hair conditioning products have long been known as state of the art and are highly valued by consumers due to their appealing appearance, ease of use, and the care benefits they provide.

[0007] These are usually leave-on products that are preferably applied (preferably sprayed) to the hair immediately after briefly mixing the two phases and condition it.

[0008] The vast majority of these products contain (cyclic) silicones in the oil phase.

[0009] From an ecological point of view and to increase consumer acceptance, there is a need for hair treatment products that are as silicone-free as possible and provide good care.

[0010] Ideally, biodegradable products should be provided.

[0011] Silicone-free two-phase products are also known and available:

[0012] In WO 2020 / 126219, silicone-free two-phase hair treatment products are proposed that contain isoparaffins and at least two different esters.

[0013] In WO 2022 / 063528, silicone-free two-phase hair treatment products are proposed that contain a specific mixture of carboxylic acid esters and carbonic acid esters.

[0014] Consumer tests sometimes find that the detangling of hair after using silicone-free products is not entirely satisfactory. Another potential disadvantage of silicone-free two-phase products can arise, particularly after regular use – especially on fine or severely damaged hair. In this context, a "burdening" of the hair is sometimes criticized, referring to a greasy or stringy appearance that necessitates more frequent, and undesirable, washing.

[0015] A further disadvantage of many silicone-free alternative products is that they often coat the hair and leave it looking unnatural, especially if a flat iron is used after drying.

[0016] The present application was therefore based on the objective of providing essentially silicone-free hair treatment products in the form of high-performance two-phase systems that could improve or eliminate the aforementioned disadvantages. 2024P00369WÖ

[0017] 2

[0018] The hair treatment products should be almost completely biodegradable and provide particularly good care for treated hair right down to the tips.

[0019] Another goal was to provide two-phase hair treatment products that do not weigh down the hair, even after regular use.

[0020] It has been found that two-phase hair treatment products containing C9-C12 alkanes as the main component in the oil phase and cationic phospholipids in the water phase largely meet the aforementioned requirements.

[0021] The presence of (cyclic) silicones is not necessary for the stability, feel, or conditioning properties of such hair treatment products, because the aforementioned active ingredients ensure the provision of two-phase systems with continuous oil and water phases that are stable over a wide temperature range (-20°C to 45°C). The two phases can be quickly and thoroughly mixed and separated again.

[0022] Furthermore, the aforementioned active ingredients in the oil and water phases of corresponding two-phase products provide a demonstrable conditioning benefit to treated hair. In particular, detangling, combability, smoothness, shine, and frizz were significantly improved, while simultaneously achieving a level of care that is at least equivalent to that of conventional two-phase hair care products containing silicones.

[0023] The present invention and preferred embodiments are characterized by the following points:

[0024] 1. Hair treatment composition comprising two superimposed layers and a common interface, containing an aqueous phase (I) and an oil phase (II), wherein the oil phase (II) comprises at least one O9-Ci2-alkane a) in a weight fraction of at least 30 wt% of the total weight of the oil phase (II) and the aqueous phase (I) comprises at least one cationic phospholipid b) of the following formula (I) in a weight fraction of 0.05 to 5 wt.- of the total weight of the water phase (I) contains, wherein 2024P00369WÖ

[0025] R 1 an alkyl, alkenyl or hydroxyalkyl group with 8 to 22 carbon atoms or an acylaminoalkyl group of the formula R 5 CONH(C m H2m)- is, in which R 5 CO is a linear acyl group with 8 to 22 carbon atoms and m = 2 or 3.

[0026] R 2 , R 3 Alkyl groups with 1 to 4 carbon atoms, or hydroxyalkyl groups with 2 to 4 carbon atoms, or carboxyalkyl groups of the formula -(CH2)z-COOM, where z has a value of 1 to 3 and M is hydrogen or an alkali metal cation, x has a value of 1 to 3, and y has a value of (3 - x).

[0027] M hydrogen or an alkali metal cation is

[0028] A is an anion.

[0029] 2. Hair treatment product according to point 1, containing the water phase (I) in a weight fraction > 80 wt.% and the oil phase (II) in a weight fraction < 20 wt.% of the total weight of the hair treatment product.

[0030] 3. Hair treatment composition according to any of the preceding points, containing at least one Cg-Ci2-alkane a) in a weight fraction of at least 40 wt.%, more preferably at least 50 wt.% and particularly preferably at least 60 wt.% of the total weight of the oil phase (II).

[0031] 4. Hair treatment preparation according to any of the preceding points, containing linear or branched O9-Ci2-alkan(s) a), selected from nonane, decane, undecane, dodecane, isononane, isodecane, isosoundecane, isododecane and mixtures thereof.

[0032] 5. Hair treatment product according to point 4, containing decane.

[0033] 6. Hair treatment product according to point 4, containing dodecane.

[0034] 7. Hair treatment products according to point 4, containing mixtures of decane and isododecane

[0035] 8. Hair treatment products according to point 4, containing mixtures of dodecane and isododecane.

[0036] 9. Hair treatment product according to one of the preceding points, containing in the oil phase (II) additionally

[0037] (i) at least one mono- and / or diester of linear or branched, saturated or unsaturated O4-Ci2-carboxylic acids with linear or branched, saturated or unsaturated O4-O24 mono- or polyols, provided that the at least one mono- or diester has at least one branch in the alcohol or acid moiety, and / or

[0038] (i) at least one vegetable oil

[0039] (ii) optional: a perfume.

[0040] 10. Hair treatment preparation according to one of the preceding points, containing as ester (i) compounds according to formula (I) 2024P00369WÖ

[0041] CH3-(CH2)m-(CHR 1 )n-COO-R 2 (I), in the

[0042] R 1 for a straight-chain or branched, saturated or unsaturated Ci-Ca alkyl group, preferably for a Ci-C4 alkyl group and most preferably for a methyl or an ethyl group, m for a number from 3 to 11, preferably for 3 to 6, n for a number from 0 to 3, preferably 0 or 1

[0043] R 2 can represent a straight-chain or branched, saturated or unsaturated Ci-C24 alkyl group, which may contain one or more -OC(O)-, -NHC(O)- or -C(OH)- groups in the chain, preferably a straight-chain saturated Ci-Cia alkyl group or a branched saturated Ci-Cia alkyl group containing one or more -OC(O)- groups in the chain

[0044] 11. Hair treatment preparation according to one of points 9 or 10, containing (i) esters of 2-ethylhexylcarboxylic acid and myristyl, cetyl and / or stearyl alcohol, particularly preferably esters known under the INCI name cetyl-2-ethylhexanoate (i).

[0045] 12. Hair treatment composition according to any one of points 9 to 11, containing ester (i) in a weight fraction of up to 20 wt.%, particularly preferably up to 15 wt.% of the total weight of the oil phase (II).

[0046] 13. Hair treatment preparations according to any of the preceding items, containing as vegetable oil (ii) amaranth seed oil, apricot kernel oil, argan oil, avocado oil, babassu oil, cottonseed oil, borage seed oil, camelina oil, safflower oil, peanut oil, pomegranate seed oil, grapefruit seed oil, hemp oil, rosehip seed oil, hazelnut oil, elderberry seed oil, blackcurrant seed oil, jojoba oil, cocoa butter, linseed oil, macadamia nut oil, corn germ oil, almond oil, marula oil, evening primrose oil, olive oil, palm oil, peach kernel oil, rapeseed oil, rice oil, sea buckthorn pulp oil, sea buckthorn kernel oil, sesame oil, shea butter, soya oil, sunflower oil, grapeseed oil, walnut oil, rosehip oil or any mixtures thereof.

[0047] 14. Hair treatment product according to point 13, containing apricot kernel oil.

[0048] 15. Hair treatment composition according to one of points 13 or 14, containing vegetable oil(s) (ii) in a weight fraction of up to 10 wt.%, particularly preferably up to 7.5 wt.% of the total weight of the oil phase (II).

[0049] 16. Hair treatment preparation according to any of the preceding points, wherein the oil phase (II) is essentially free of other oils in addition to Cg-Ci2-alkan(s) a) and optionally ester(s) (i), vegetable oil(s) (ii) and perfume(s) (iii).

[0050] 17. Hair treatment composition according to any of the preceding items, containing the cationic phospholipid b) in a weight fraction of 0.05 to 4 wt.% and in particular 0.05 to 3 wt.% of the total weight of the aqueous phase (I). 2024P00369WG

[0051] 18. Hair treatment composition according to any of the preceding items, wherein the cationic phospholipid b) is selected from compounds of formula (1), wherein

[0052] R 1 a decylamidopropyl group, laurylamidopropyl group, cocamidopropyl group, myristylamidopropyl group or a cetylamidopropyl group means R 2 , R 3 Methyl groups represent x for 2 and y for 1.

[0053] M for an alkali cation

[0054] A- stands for a halide or a Ci-C4 alkyl sulfate ion.

[0055] 19. Hair treatment products according to point 18, containing cationic phospholipids known under the INCI name Myristylamidopropyl PG Dimonium Chloride Phosphate and / or Cocamidopropyl PG Dimonium Chloride Phosphate b).

[0056] 20. Hair treatment composition according to any of the preceding points, wherein the aqueous phase (I) additionally contains at least one cationic surfactant other than b) in a weight fraction of 0.05 to 5 wt% of the total weight of the aqueous phase (I).

[0057] 21. Hair treatment preparation according to point 20, wherein the aqueous phase (I) comprises at least one additional cationic surfactant selected from distearyldimethylammonium chloride, lauryltrimethylammonium chloride, lauryltrimethylbenzylammonium chloride,

[0058] Tricetylmethylammonium chloride, cetyltrimethylammonium chloride,

[0059] Cetyltrimethylammonium bromide, cetyltrimethylammonium methosulfate,

[0060] Stearyltrimethylammonium chloride, Behenyltrimethylammonium chloride,

[0061] Contains behenyltrimethylammonium bromide and behenyltrimethylammonium methosulfate.

[0062] 22. Hair treatment product according to any of the preceding points, wherein the aqueous phase (I) contains cetyltrimethylammonium chloride (INCI name: Cetrimonium Chloride).

[0063] 23. Hair treatment composition according to any of the preceding points, wherein the aqueous phase (I) additionally contains at least one C2-Ce polyol in a weight fraction of 0.5 to 5 wt% of the total weight of the aqueous phase (I).

[0064] 24. Hair treatment composition according to any of the preceding items, wherein the aqueous phase (I) contains glycerin in a weight fraction of 0.5 to 5 wt% of the total weight of the aqueous phase (I).

[0065] 25. Hair treatment composition according to any of the preceding points, wherein the aqueous phase (I) additionally contains at least one hair fiber repair agent in a weight fraction of 0.01 to 10 wt.% of the total weight of the aqueous phase (I), preferably a. a mixture of hydroxypropyl gluconamide and hydroxypropyl ammonium gluconate and / or b. alpha-hydroxyoctanal or alpha-hydroxyoctanone and / or 2024P00369WÖ

[0066] 6 c. e-Polylysine.

[0067] 26. Hair treatment composition according to any of the preceding points, wherein the water phase (I) contains water in a weight fraction of at least 85 wt.%, preferably at least 87.5 wt.% and particularly preferably at least 90 wt.% of the total weight of the water phase (I).

[0068] 27. Hair treatment product according to any of the preceding items, which is essentially free of cationic polymers.

[0069] 28. Cosmetic procedure for the care of hair, in which a hair treatment product is applied (preferably sprayed) to the damp or dry hair after vigorous shaking, following one of the preceding points, and left on the hair until the next hair washing.

[0070] 29. Cosmetic use of a hair treatment product according to one of the preceding points for the care of hair.

[0071] 30. Cosmetic use according to point 29 for the care of hair to improve detangling, combability, smoothness, shine and frizz of hair.

[0072] The hair treatment products according to the invention comprise two optically separated layers (phases) which can be homogenized by shaking, and which separate again in the resting state into two separate, optically recognizable layers with a common interface.

[0073] The emulsion produced by shaking is preferably stable for at least 30 seconds, more preferably at least 1 minute, particularly preferably at least 5 minutes and especially preferably at least 10 minutes before it begins to separate back into the original two layers.

[0074] For rapid mixing and separation of the two layers, it can be advantageous if the water phase (I) and the oil phase (II) have lower viscosity values. Within the scope of the present invention, "lower viscosity values" preferably refer to viscosity values ​​of the water phase (I) and the oil phase (II) of up to a maximum of 1000 mPas each, more preferably 600 mPas, and particularly 400 mPas (measured at 20°C with a Brookfield viscometer DV-II, spindle 2 at 20 rpm).

[0075] For better visibility of the mixing and separation of the two layers, it may also be advantageous if at least one of the layers (phases) (I) or (II) is transparent.

[0076] Under this condition, sufficient mixing of the two phases can preferably be recognized by the fact that only a single phase is visible, which may be opaque to milky. 2024P00369WÖ

[0077] 7

[0078] In particular, at least one of the two phases (I) and (II) is preferably transparent.

[0079] In the context of the present invention, “transparency” means that the water phase (I) and / or the oil phase (II) in the state of rest preferably has an NTU (Nephelometry Turbidity Unit) value of a maximum of 100, preferably of a maximum of 75, more preferably of a maximum of 50 and in particular of a maximum of 25 (measured, for example, with a Turbiquant® type turbidimeter from Merck).

[0080] In a preferred embodiment, the water phase (I) is transparent to slightly cloudy and the oil phase (II) of the care phase is milky-creamy.

[0081] For better visualization, one of the two phases (I) or (II), preferably the aqueous phase (I), can be colored with a cosmetically acceptable dye.

[0082] It is further desirable and preferred that the hair treatment products according to the invention are sprayable.

[0083] In sprayable form, the hair treatment products according to the invention are suitable for application from a pump dispenser. An advantage of this application method is its simple, clean, and time-saving handling, as the hair treatment products can be evenly distributed as a fine spray mist from a suitable pump dispenser by simply pressing a pump valve, reaching all areas of the hair.

[0084] This way, the hands do not come into contact with the product and do not need to be cleaned after use.

[0085] For such an application method, the ready-to-use (i.e., homogenized by shaking) hair treatment agents according to the invention preferably have a viscosity of at most 1000 mPas, preferably at most 800 mPas, more preferably at most 600 mPas and in particular at most 500 mPas (each measured at 20°C with a Brookfield viscometer DV-II, spindle 2 at 20 rpm).

[0086] It is also preferred for such an application method that the hair conditioning agents according to the invention are free of propellants.

[0087] In a preferred embodiment, the hair treatment compositions according to the invention contain a) the water phase (I) in a weight fraction of at least 80 wt.%, preferably at least 85 wt.%, and particularly at least 88 wt.% of the total weight of the hair treatment composition, and b) the oil phase (II) in a weight fraction of at most 20 wt.%, preferably at most 15 wt.%, and particularly at most 12 wt.% of the total weight of the hair treatment composition. 2024P00369WÖ

[0088] 8

[0089] Within the scope of the present invention, it is further preferred if the water phase (I) contains at least 85 wt.%, preferably at least 87.5 wt.% and in particular at least 90 wt.% water, based on its total weight.

[0090] The oil phase (II) contains at least one O9-Ci2-alkane a) in a weight fraction of at least 30 wt% of the total weight of the oil phase.

[0091] More preferred are weight fractions of at least 40 wt.%, further preferred at least 50 wt.% and particularly preferred at least 60 wt.% of the total weight of the oil phase (II).

[0092] In a preferred embodiment, the oil phase (II) additionally comprises

[0093] (i) at least one mono- and / or diester of linear or branched, saturated or unsaturated O4-Ci2-carboxylic acids with linear or branched, saturated or unsaturated O4-O24 mono- or polyols, provided that the at least one mono- or diester has at least one branch in the alcohol or acid moiety, and / or

[0094] (ii) at least one vegetable oil

[0095] (iii) optional: a perfume, wherein

[0096] Esters (i) may preferably be present in a weight fraction of up to 20 wt.%, particularly preferably up to 15 wt.% of the total weight of the oil phase (II), vegetable oil(s) (ii) may be present in a weight fraction of up to 10 wt.%, particularly preferably up to 7.5 wt.% of the total weight of the oil phase (II).

[0097] It was found that hair care products which essentially contain only the previously defined oils a) and possibly (i) to (iii) in the oil phase (II) exhibit particularly satisfactory care benefits.

[0098] Higher amounts of O9-Ci2-alkan(s) a) in the oil phase (II) result in particularly good spreadability and a light texture of the hair care products (comparable to two-phase products containing cyclomethicones).

[0099] Compared to silicone-free two-phase products containing or based on carbonic acid esters in the oil phase, the advantage was achieved that, by carefully balancing the amounts of oil(s) a) and, if applicable, (i) to (iii) in the oil phase (II), no overburdening occurs even with regular use, and the previously described negative interactions do not occur during subsequent treatment with a flat iron. 2024P00369WÖ

[0100] 9

[0101] In a further preferred embodiment, the hair treatment products according to the invention contain in the oil phase (II) - in addition to the oils a) and optionally (i) to (iii) - essentially no further oils.

[0102] In this context, ‘essentially none’ means that the oil phase (II) preferably contains at most 1 wt.%, more preferably at most 0.5 wt.% and particularly preferably at most 0.1 wt.% of different oils from a) to d).

[0103] O9-Ci2-Alkanes a) are particularly suitable as silicone substitutes in hair care products due to their ability to give shine and softness to the hair without causing it to become heavy or greasy when used regularly.

[0104] It has been found that medium-chain alkanes (i.e., alkanes containing 9 to 12 carbon atoms) are more suitable for use in the compositions according to the invention than longer-chain alkanes (C13, C14, C15, C16, C17, C18, C19), since higher levels of longer-chain alkanes can exhibit a certain degree of “overburdening” and also the problems previously described in subsequent hair treatment with a flat iron.

[0105] Examples of suitable O9-Ci2-alkanes a) within the meaning of the present invention are both linear and branched O9-Ci2-alkanes, which may be selected from nonane, decane, undecane, dodecane, isononane, isodecane, isosoundecane, isododecane and any mixtures thereof.

[0106] In a particularly preferred embodiment, the hair treatment compositions according to the invention contain decane in the oil phase (II) in a weight fraction of 30 wt.%, more preferably 40 wt.%, particularly preferably at least 50 wt.% and particularly preferably at least 60 wt.% of the total weight of the oil phase (II).

[0107] In a further particularly preferred embodiment, the hair treatment products according to the invention contain dodecane in the oil phase (II) in a weight fraction of at least 30 wt.%, more preferably 40 wt.%, particularly preferably at least 50 wt.% and particularly preferably at least 60 wt.% of the total weight of the oil phase (II).

[0108] In a further particularly preferred embodiment, the hair treatment compositions according to the invention contain in the oil phase (II) mixtures of decane and isododecane in a weight fraction of at least 30 wt.%, more preferably 40 wt.%, particularly preferably at least 50 wt.% and particularly preferably at least 60 wt.% of the total weight of the oil phase (II). 2024P00369WÖ

[0109] 10

[0110] In a further particularly preferred embodiment, the hair treatment compositions according to the invention contain in the oil phase (II) mixtures of dodecane and isododecane in a weight fraction of at least 30 wt.%, more preferably 40 wt.%, particularly preferably at least 50 wt.% and particularly preferably at least 60 wt.% of the total weight of the oil phase (II).

[0111] Examples of particularly suitable O9-Ci2-alkanes a) are the commercially available products Purolan® IDD (INCI name: Isododecane), Parafol® 10 (INCI name: Decane) and Parafol® 12 (INCI name: Dodecane).

[0112] Suitable Cg-Ci2-alkanes a) can also be used in the oil phase (II) of the compositions according to the invention as a mixture with one or more ester(s) (i), for example as the commercial product Lexfeel® D5 (available from Inolex; INCI name: Neopentyl Glycol Diheptanoate, Isododecane).

[0113] Suitable esters (i) are preferably mono- and / or diesters of linear or branched, saturated or unsaturated C4-Ci2 carboxylic acids with linear or branched, saturated or unsaturated C4-C24 mono- or polyols, provided that the at least one mono- or diester has at least one branch in the alcohol or acid moiety.

[0114] Esters (i) combine well with Cg-Ci2 alkanes (a) and vegetable oils (ii) and, after mixing with the water phase (I), can be distributed on the hair without weighing it down. It has been found that branched esters (i) offer unexpected advantages compared to purely unbranched oils. For example, branched esters (i) show a lower tendency—especially with frequent use—to contribute to weighing down the hair.

[0115] Furthermore, branched esters (i) penetrate the hair fibers more quickly and provide a long-lasting, light, non-greasy conditioning feeling.

[0116] At the same time, esters (i) form a kind of protective film around the hair fibers due to their branched structure, making hair smoother and more supple and easier to comb. Thus, a significant reduction in frizz is also noticeable after using the products according to the invention.

[0117] Preferred branched esters (i) may be selected from esters of formula (I) CH3-(CH2)m-(CHR 1 )n-COO-R 2 (I), in the

[0118] R 1 for a straight-chain or branched, saturated or unsaturated Ci-Ca alkyl group, m for a number from 3 to 11, n for a number from 0 to 3 and R 2 can represent a straight-chain or branched, saturated or unsaturated Ci-C24 alkyl group, which may contain one or more -OC(O)-, -NHC(O)- or -C(OH)- groups in the chain.

[0119] In more preferred esters (i) of the aforementioned formula (I)

[0120] R 1 for a straight-chain Ci-C4 alkyl group, most preferably for a methyl or an ethyl group, m for the numbers 3 to 6, n for the numbers 0 or 1 and

[0121] R 2for a straight-chain saturated Ci-Cia alkyl group or for a branched saturated Ci-Cia alkyl group containing one or more -OC(O)- groups in the chain.

[0122] Particularly preferred esters (i) according to formula (I) are esters of cross-linked Cs-Cs carboxylic acids and Ci2-C24 monoalcohols, preferably esters of 2-ethylhexyl carboxylic acid and myristyl, cetyl and / or stearyl alcohol and especially esters known under the INCI name cetyl ethylhexanoate.

[0123] It is advantageous to add smaller amounts of vegetable oils (ii) to the oil phase (II) of hair treatment compositions according to the invention. This allows compositions according to the invention to be further enriched with ingredients of natural origin that condition the hair without weighing it down.

[0124] Suitable vegetable oils (ii) within the scope of the present invention are understood to be amaranth seed oil, apricot kernel oil, argan oil, avocado oil, babassu oil, cottonseed oil, borage seed oil, camelina oil, safflower oil, peanut oil, pomegranate seed oil, grapefruit seed oil, hemp oil, rosehip seed oil, hazelnut oil, elderberry seed oil, blackcurrant seed oil, jojoba oil, cocoa butter, linseed oil, macadamia nut oil, corn germ oil, almond oil, marula oil, evening primrose oil, olive oil, palm oil, peach kernel oil, rapeseed oil, rice oil, sea buckthorn pulp oil, sea buckthorn kernel oil, sesame oil, shea butter, soybean oil, sunflower oil, grapeseed oil, walnut oil, rosehip oil, or any mixtures thereof. A particularly preferred vegetable oil (ii) is apricot kernel oil.

[0125] As an essential conditioning component in the aqueous phase (I), hair treatment products according to the invention contain at least one cationic phospholipid (KPL) b) according to formula (1) in a weight fraction of 0.05 to 5 wt.% of the total weight of the aqueous phase (I). Weight fractions of 0.05 to 4 wt.% are preferred and 0.05 to 3 wt.% are particularly preferred.

[0126] These specific cationic surfactants have the advantage of significantly improving the conditioning properties of hair, especially its wet combability. 2024P00369WG

[0127] 12

[0128] Preferred alkyl groups with 8 to 22 carbon atoms are selected from n-octyl, n-nonyl, n-decyl, n-undecyl, lauryl, n-tridecanyl, myristyl, n-pentadecanyl, cetyl, palmityl, stearyl, elaidyl, arachidyl, behenyl, and cocoyl groups. A representative cocoyl group consists, based on its total weight, of 4–9 wt% n-octyl, 4–9 wt% n-decyl, 45–55 wt% lauryl, 15–21 wt% myristyl, 8–13 wt% palmityl, and 7–14 wt% stearyl groups. Preferred alkenyl groups with 8 to 22 carbon atoms are selected from a linoleyl group ((9Z,12Z)-octadeca-9,12-dien-1-yl) and a linolenyl group ((9Z,12Z,15Z)-octadeca-9,12,15-trien-1-yl). A preferred hydroxyalkyl group with 8 to 22 carbon atoms is selected from a 12-hydroxystearyl group.

[0129] Particularly favored cationic phospholipids of formula (1) are those in which R 1 an acylaminoalkyl group of the formula R 5 CONH(C m H2m)- is, in which R 5CO represents a linear acyl group with 8 to 22 carbon atoms and m = 3.

[0130] Preferred linear acyl groups R 5 CO with 8 to 22 carbon atoms are selected from n-octanoyl, n-nonanoyl, n-decanoyl, n-undecanoyl, lauroyl, n-tridecanoyl, myristoyl, n-pentadecanoyl, cetoyl, palmitoyl, stearoyl, elaidoyl, arachidoyl, behenoyl, and cocoyl groups. A representative cocoyl group consists, based on its total weight, of 4–9 wt% n-octanoyl, 4–9 wt% n-decanoyl, 45–55 wt% lauroyl, 15–21 wt% myristoyl, 8–13 wt% palmitoyl, and 7–14 wt% stearoyl groups. Particularly preferred linear acyl groups R 5 CO are selected from a decyl group, a cocoyl group, a lauroyl group (n-CnH23CO), a myristoyl group (n-Ci3H27CO), a cetyl group (n-CisHsiCO) and a linolenyl group ((9Z,12Z)-Octadeca-9, 12-dien-1-oyl).

[0131] Highly preferred linear acyl groups R 5CO are selected from a cocoyl group, a lauroyl group (n-CnH23CO) and a myristoyl group (n-Ci3H27CO).

[0132] Preferred alkyl groups with 1 to 4 carbon atoms are methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 2-methylpropyl, and tert-butyl groups. The methyl group is particularly preferred. Preferred hydroxyalkyl groups with 2 to 4 carbon atoms are 2-hydroxyethyl and 1-hydroxyethyl groups.

[0133] Preferred carboxyalkyl groups of the formula -(CH2)z-COOM with z = 1 to 3 are carboxymethyl, carboxyethyl and carboxy-n-propyl groups.

[0134] Preferred alkali metal cations are selected from sodium and potassium cations; Na + is particularly preferred. Preferred anions are selected from sulfate, chloride, phosphate, nitrate, bicarbonate and acetate, with one chloride anion being particularly preferred.

[0135] In a preferred embodiment, the hair treatment compositions according to the invention contain at least one cationic phospholipid (KPL) according to formula (1), wherein

[0136] R 1 a decylamidopropyl group, laurylamidopropyl group, cocamidopropyl group, myristylamidopropyl group or a cetylamidopropyl group means 2024P00369WG

[0137] 13

[0138] R 2 , R 3 Methyl groups represent x for 2 and y for 1.

[0139] M for an alkali cation

[0140] A- stands for a halide or a Ci-C4 alkyl sulfate ion.

[0141] Particularly preferred KPL according to formula (1) are known and commercially available, for example under the trade names Ariasilk® PTM (INCI name: Myristamidopropyl PG- Dimonium Chloride Phosphate) or Ariasilk® PTC (INCI name: Cocamidopropyl PG- Dimonium Chloride Phosphate).

[0142] In a further preferred embodiment, the hair treatment products according to the invention additionally contain in the aqueous phase (I) at least one cationic surfactant other than b) in a weight fraction of 0.05 to 5 wt.% of the total weight of the aqueous phase (I).

[0143] The cationic surfactants are particularly preferably used in weight fractions of 0.06 to 4 wt.%, most preferably of 0.07 to 3.5 wt.% and especially of 0.075 to 3 wt.% of the total weight of the aqueous phase (I).

[0144] It was found that by combining KPL b) with at least one other cationic surfactant, the hair care effect of the hair treatment products according to the invention can be further enhanced, in particular the detangling ability.

[0145] Suitable cationic surfactants for use in the hair treatment products according to the invention are preferably linear or branched, saturated or unsaturated physiologically compatible Ci-C24-alkyltri(Ci-C4)-alkylammonium salts, Di-Ci-C24-alkyldi(Ci-C4)-alkylammonium salts or Tri-Ci-C24-alkyl(Ci-C4)-alkylammonium salts and / or primary, secondary or tertiary amines containing at least one group R-CO(NH)-(CH2)n-, in which R represents a linear or branched, saturated or unsaturated alkyl group with 7 to 21 C atoms and n represents an integer from 1 to 4.

[0146] Particularly preferred Ci-C24-alkyltri(Ci-C4)-alkylammonium salts, Di-Ci-C24-alkyldi(Ci-C4)-alkylammonium salts or Tri-Ci-C24-alkyl(Ci-C4)-alkylammonium salts are, for example, halide and / or methosulfate salts, in particular chlorides, bromides and methosulfates, such as distearyldimethylammonium chloride, lauryltrimethylammonium chloride, lauryltrimethylbenzylammonium chloride, tricetylmethylammonium chloride,

[0147] Cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, cetyltrimethylammonium- 2024P00369WG

[0148] 14 methosulfate, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, behenyltrimethylammonium bromide and behenyltrimethylammonium methosulfate.

[0149] Cetyltrimethylammonium and / or behenyltrimethylammonium salts are particularly preferred, especially cetyltrimethylammonium salts containing a methosulfate and / or chloride ion as an anion.

[0150] Particularly preferred primary, secondary or tertiary amines containing at least one group R-CO(NH)-(CH2)n-, in which R represents a linear or branched, saturated or unsaturated alkyl group with 7 to 21 C atoms, and n represents an integer from 1 to 4, are known under the name “amidoamines”.

[0151] Suitable amidoamines can be present in the hair conditioning agents both as such and (as a result of protonation in a suitably acidic solution) in the form of their respective quaternary compound.

[0152] Non-cationic amidoamines are preferred.

[0153] Particularly suitable amidoamines may be selected from brassicamidopropyldimethylamine, lauramidopropyldimethylamine, myristamidopropyldimethylamine, stearamidopropyldimethylamine, cocamidopropyldimethylamine, ricinolamidopropyldimethylamine, isostearamidopropyldimethylamine, oleamidopropyldimethylamine, behenamidopropyldimethylamine, palmamidopropyldimethylamine, or mixtures thereof. Brassicamidopropyldimethylamine, behenamidopropyldimethylamine, stearamidopropyldimethylamine, or mixtures thereof are particularly preferred.

[0154] Stearamidopropyl dimethylamine is particularly preferred.

[0155] In a further preferred embodiment, the hair treatment products according to the invention contain at least one C2-Ce polyol in the aqueous phase (I) in a weight fraction of 0.5 to 5 wt.% of the total weight of the aqueous phase (I).

[0156] C2-Ce polyols are particularly preferred in weight fractions of 0.6 to 4 wt.%, most preferably of 0.7 to 3.5 wt.% and especially of 0.75 to 3 wt.% of the total weight of the aqueous phase (I).

[0157] C2-Ce polyols enhance the hair care effect of the hair treatment products according to the invention and prevent foaming of the cationic surfactants.

[0158] Suitable C2-Ce polyols within the meaning of the present invention are preferably understood to be polyols containing in their molecule 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms, and 2 to 6 hydroxyl groups, preferably 2 to 3 hydroxyl groups. Examples of preferred C2-Ce polyols are: ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, dipropylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, isopropylene glycol, 1,2-pentanediol, 1,3-pentanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, sorbitol, or mixtures thereof. 2024P00369WG

[0159] 15

[0160] Polyols. Particularly preferred are 1,2-propylene glycol, glycerin, 1,3-butylene glycol, 1,6-hexanediol, diglycerin and / or dipropylene glycol; glycerin is especially preferred.

[0161] In a further preferred embodiment, the hair treatment products according to the invention contain in the water phase (I) at least one repair agent for hair fibers in a weight fraction of 0.01 to 10 wt.% of the total weight of the water phase (I).

[0162] Suitable repair agents for hair fibers include, for example, a. compounds of the following formulas (I) or (II) and / or b. compounds of the following formula (III) and / or

[0163] R 7 -C(O)-CH(X)-R 8 (III) c. e-Polylysine to understand, where in formulas (I), (II) and (III)

[0164] R1-R4 are independently hydrogen, a hydrocarbon radical with 1 to 10 carbon atoms, a hydroxyl group, an amino group, a sulfhydryl group, an aryl group or a halogen; and R5 and Re are independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aryl group, an alkylaryl group or a heterocyclic group; and

[0165] R1 - R4' are independently hydrogen, a hydrocarbon radical with 1 to 10 carbon atoms, a hydroxyl group, an amino group, a sulfhydryl group, an aryl group or a halogen, and R5 and Re are independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aryl group or a heterocyclic group, excluding that R5' and Re' are simultaneously hydrogens, 2024P00369WG

[0166] 16 the aliphatic hydrocarbon group, the alicyclic hydrocarbon group, the aryl group, the alkylaryl group or the heterocyclic group are substituted with at least one hydroxyl group, one of the residues R 7 or R 8 for H and the other for a straight-chain or branched, saturated or unsaturated alkyl group with 1 to 15 carbon atoms, wherein the carbon chain may optionally be substituted with one or more hydroxyl or amino groups, and

[0167] X represents -OH, -NH2, -CI, -Br, -I or the following groupings: -O-(CH2)n-CH3, where n represents the numbers 1, 2, 3 or 4, and -O-(CH2)m-OH, where m represents the numbers 1, 2 or 3.

[0168] Particularly preferred among suitable repair agents for hair fibers are a. mixtures of hydroxypropylgluconamide and hydroxypropylammonium gluconate and / or b. alpha-hydroxyoctanal or alpha-hydroxyoctanone and / or c. e-polylysine.

[0169] In a further preferred embodiment, the hair treatment products according to the invention may contain in the aqueous phase (I) active ingredients for pH regulation, preferably acids such as, in particular, acetic acid, citric acid, malic acid, maleic acid, formic acid, sulfonic acid, phosphoric acid, phosphonic acids, D-lactic acid, L-lactic acid, D / L-lactic acid, oxalic acid, succinic acid or bases such as, in particular, sodium hydroxide.

[0170] Advantageously, the hair treatment products according to the invention contain in the aqueous phase (I) active ingredients for pH regulation in amounts of 0.01 - 5 wt.%, preferably 0.01 - 3 wt.% and in particular of 0.01 to 2 wt.% (based on the total weight of the hair treatment product).

[0171] Preferably, active ingredients for pH regulation are used in the hair treatment products according to the invention, which, in addition to their function of adjusting the pH value, can also provide positive properties for the hair and / or scalp. In this context, lactic acid, citric acid and / or succinic acid are particularly noteworthy, as these acids can support skin moisture regulation on the scalp, contribute to the repair of hair fibers and, if applicable, support color protection on dyed hair.

[0172] The products according to the invention exhibit the care benefits described above without the need for the addition of silicones. 2024P00369WG

[0173] 17

[0174] In comparison to previous silicone-free two-phase products, the hair treatment products according to the invention also have the advantage that they do not contain any cationic polymers in the water phase in order to achieve excellent care benefits.

[0175] This not only further increases the biodegradability of the hair treatment products (especially compared to earlier products containing synthetic, so-called "polyquaternium" polymers, for example, polyquaternium-16) but also reduces their complexity. The use of cationic polymers of natural origin in hair treatment products according to the invention—such as cationic guar polymers—has sometimes proven disadvantageous. In particular, in cases where flat irons were used after treatment with silicone-free two-phase products containing cationic guar polymers (at temperatures between 190 and 230°C), the hair became sticky, hard, and stiff after straightening, and the formation of steam and an unpleasant odor could be observed.

[0176] In a particularly preferred embodiment, hair treatment products according to the invention are therefore essentially free of cationic polymers.

[0177] For the purposes of the present invention, "essentially free" preferably means that the hair treatment compositions contain cationic polymers in a weight fraction of no more than 0.01 wt.% of the total weight of the hair treatment compositions. More preferred are maximum contents of cationic polymers of 0.005 wt.%, further preferred a maximum of 0.001 wt.%, and most preferably 0 wt.%.

[0178] It was found that for particularly good stability of the two phases (I) and (II) of the hair treatment product according to the invention, it is advantageous if they contain only certain surfactants and / or emulsifiers in certain quantities.

[0179] In this context, "stability" means that the two phases quickly separate again after mixing and form a sharp horizontal phase boundary, at which, ideally, no turbidity occurs over a long period of time and under temperature fluctuations.

[0180] In a preferred embodiment, the hair treatment products according to the invention contain a maximum of 1 wt.%, more preferably a maximum of 0.8 wt.%, particularly preferably a maximum of 0.6 wt.% and in particular a maximum of 0.5 wt.% anionic, amphoteric, zwitterionic and / or non-ionic surfactants (based on the total weight of the hair treatment product).

[0181] Within this embodiment, it is particularly preferred if the hair treatment compositions according to the invention do not contain anionic, amphoteric, zwitterionic and / or nonionic surfactants. 2024P00369WÖ

[0182] 18

[0183] As already stated earlier in this application, it is not necessary to add further components (oils and fats) to the oil phase (II) for the conditioning effect and the stability of the hair treatment products according to the invention.

[0184] In particular, silicones can be omitted.

[0185] Perfume oils are not to be included among the aforementioned oils and fats in this context.

[0186] The hair conditioning agents according to the invention preferably have a pH value in the range of 2 to 7, preferably from 2.5 to 6, particularly preferably from 3 to 5 and especially from 3 to 4.5.

[0187] In addition to their aesthetic appearance, the two-layer hair treatment products according to the invention have the advantage of being easy to use and simple to manufacture. The special combination of active ingredients in the hair treatment products ensures rapid mixing of the two layers before application and thorough separation of the two layers in the resting state after application. The hydrophilic phase is predominantly water-based, which meets consumer needs. Furthermore, the hair treatment products according to the invention are particularly suitable for hair care. The presence of (cyclic) silicones is not necessary for either the stability or the conditioning properties of the hair treatment products, as the hair treatment products according to the invention exhibit comparable conditioning benefits on treated hair compared to products containing silicones.In particular, the detangling, combability, smoothness, shine, and frizz of the hair were significantly improved. The hair treatment products according to the invention are sprayable and suitable for application from a pump dispenser. This makes them easy to use and effective, as the fine mist dispensed from the pump reaches all areas of the hair.

[0188] A second object of the invention is a cosmetic method for the care of hair, in which a hair treatment product is applied (preferably sprayed) to the moist or dry hair after vigorous shaking according to one of the preceding points and left on the hair until the next hair washing.

[0189] A third object of the invention is the cosmetic use of the hair treatment product according to the invention for the care of hair, in particular for improving the detangling, combability, smoothness, shine and frizz of hair.

[0190] The same applies to the method and use according to the invention as has been said regarding the means according to the invention. The following examples are intended to describe the subject matter of the invention in more detail, without limiting it thereto.

[0191] 2024P00369WÖ

[0192] 20

[0193] Examples:

[0194] The following compositions according to the invention EZ (I) to (VI) as well as the comparison compositions VZ (VII) were produced.

[0195] All quantities are given in % by weight (in the entire composition):

[0196] 1 INCI name: Dodecane (Sasol)

[0197] 2 INCI name: Decane (Sasol)

[0198] 3 INCI name: Undecane, Tridecane (BASF)

[0199] 4 INCI name: Cetyl Ethylhexanoate (Lubrizole)

[0200] 5 INCI name: Myristamidopropyl PG Dimonium Chloride Phosphate (Croda)

[0201] 6 INCI name: Cocamidopropyl PG Dimonium Chloride Phosphate (Croda)

[0202] Application tests revealed that overburdening of treated hair increases with increasing carbon chain length of alkane a) (for example, when using a mixture of Cn / C₂ alkanes (Cetiol® Ultimate)). An optimal chain length of alkane a) with 9 to 12 carbon atoms was found. Optimal conditioning was achieved by combining alkane a) in the oil phase and cationic phospholipids in the water phase. Conditioning could be further enhanced by adding a cationic alkylquat to the water phase in addition to the cationic phospholipid (particularly improving wet combability and detangling).

Claims

2024P00369WÖ Patent claims:

1. Hair treatment composition comprising two superimposed layers and a common interface, containing an aqueous phase (I) and an oil phase (II), wherein the oil phase (II) comprises at least one O9-Ci2-alkane a) in a weight fraction of at least 30 wt% of the total weight of the oil phase (II) and the aqueous phase (I) comprises at least one cationic phospholipid b) of the following formula in a weight fraction of 0.05 to 5 wt.- of the total weight of the water phase (I), wherein R 1 an alkyl, alkenyl or hydroxyalkyl group with 8 to 22 carbon atoms or an acylaminoalkyl group of the formula R 5 CONH(C m H2m)- is, in which R 5 CO is a linear acyl group with 8 to 22 carbon atoms and m = 2 or 3. R 2 , R 3Alkyl groups with 1 to 4 carbon atoms, or hydroxyalkyl groups with 2 to 4 carbon atoms, or carboxyalkyl groups of the formula -(CH2)z-COOM, where z has a value of 1 to 3 and M is hydrogen or an alkali metal cation, x has a value of 1 to 3, and y has a value of (3 - x). M hydrogen or an alkali metal cation is A is an anion.

2. Hair treatment composition according to claim 1, comprising linear or branched Cg-Ci2-alkan(s) a), selected from nonane, decane, undecane, dodecane, isononane, isodecane, isosoundecane, isododecane and mixtures thereof.

3. Hair treatment composition according to one of the preceding claims, comprising in the oil phase (II) additionally (i) at least one mono- and / or diester of linear or branched, saturated or unsaturated C4-Ci2 carboxylic acids with linear or branched, saturated or unsaturated C4-C24 mono- or polyols, 2024P00369WÖ 22 provided that the at least one mono- or diester has at least one branch in the alcoholic or acidic moiety, and / or (ii) at least one vegetable oil (iii) optional: a perfume.

4. Hair treatment composition according to any one of the preceding claims, wherein the cationic phospholipid b) is selected from compounds of formula (1), wherein R 1 a decylamidopropyl group, laurylamidopropyl group, cocamidopropyl group, myristylamidopropyl group or a cetylamidopropyl group R 2 , R 3 Methyl groups represent x for 2 and y for 1. M for an alkali cation A- stands for a halide or a Ci-O4 alkyl sulfate ion.

5. Hair treatment composition according to any of the preceding claims, wherein the aqueous phase (I) additionally contains at least one cationic surfactant other than b) in a weight fraction of 0.05 to 5 wt.% of the total weight of the aqueous phase (I).

6. Hair treatment composition according to any of the preceding claims, wherein the aqueous phase (I) additionally contains at least one C2-Ce polyol in a weight fraction of 0.5 to 5 wt.% of the total weight of the aqueous phase (I).

7. Hair treatment composition according to any of the preceding claims, wherein the water phase (I) additionally contains at least one repair agent for hair fibers in a weight fraction of 0.01 to 10 wt.% of the total weight of the water phase (I).

8. Hair treatment composition according to any of the preceding claims, wherein the water phase (I) contains water in a weight fraction of at least 85 wt.% of the total weight of the water phase (I).

9. Hair treatment composition according to any of the preceding claims, which is substantially free of cationic polymers.

10. Cosmetic use of a hair treatment product according to any of the preceding claims for the care of hair to improve detangling, combability, smoothness, shine and frizz of hair.

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