Increased solubilization of diethylaminohydroxybenzoyl hexyl benzoate

Abstract

The present invention relates to a cosmetic composition comprising an ester of a fatty acid with dextrin, a mixture of branched and linear saturated C15-C19, wherein the mixture mainly comprises branched saturated C15-C19 and a UV filter of formula (I). This cosmetic composition allows a high solubilization of the UV filter of formula (I), which makes the composition have a very high absorption of harmful UV light, i.e. the present invention relates to a composition with a high sun protection factor (SPF).

Description

Technical Field

[0001] This invention relates to the field of cosmetic compositions that protect against ultraviolet (UV) light, and particularly to cosmetic compositions comprising the UV filter diethylaminohydroxybenzoylhexylbenzoate. Background Technology

[0002] Diethylaminohydroxybenzoylhexylbenzoate is a highly effective UV(A) filter with a relatively broad absorption spectrum for harmful UV light and is widely used in cosmetic compositions. It has moderate solubility, especially in esters and alcohols. However, its solubility in water and alkanes is very low.

[0003] For cosmetic compositions to be accepted, good sensory properties are important. Skin feel, in particular, is crucial. Products that produce a silky or velvety feel upon touch, or a fresh and smooth sensation, and have a soft finish or a comfortable afterfeel, are significantly better accepted in the market.

[0004] Traditionally, silicone oils have been used to improve sensory properties in this area. However, with increasing market pressure on the use of silicone oils in cosmetics, particularly due to environmental and regulatory concerns, there is a growing search for alternatives that enhance sensory properties.

[0005] Liquid C8-C30 alkanes have been found to be useful for improving sensory properties and have been suggested as an alternative to silicone oils.

[0006] For example, WO 2018 / 109353 A1 discloses a mixture of branched and straight-chain saturated C15-C19 alkanes to improve the sensory properties of oil-in-water emulsions.

[0007] However, replacing the solvent in the cosmetic composition with this liquid alkane to achieve improved sensory properties significantly reduces the solubility of the UV filter diethylaminohydroxybenzoylhexylbenzoate, and thus leads to a sharp decrease in the sun protection factor (SPF) of the corresponding cosmetic composition. Summary of the Invention

[0008] Therefore, the problem to be solved by the present invention is to obtain high solubility of diethylaminohydroxybenzoylhexylbenzoate, a UV filter containing liquid C8-C30 alkanes, especially C15-C19 alkanes, in cosmetic compositions having particularly improved sensory properties.

[0009] Surprisingly, it has been found that the cosmetic composition according to claim 1 allows for solving this problem.

[0010] It has been specifically found that this solution represents a highly sustainable and advantageous approach to this problem because fatty acid esters are available from biological resources. This solution is even more attractive because a preferred mixture of C15-C19 alkanes is also available from biological sources. Therefore, cosmetic compositions with high sun protection factor (SPF) and excellent sensory properties can be provided.

[0011] Other aspects of the invention are the subject of the other independent claims. Particularly preferred embodiments are the subject of the dependent claims. Detailed Implementation

[0012] In a first aspect, the present invention relates to a cosmetic composition comprising...

[0013] - Fatty acids and dextrin esters

[0014] -A mixture of branched and straight-chain saturated C15-C19 alkanes

[0015] UV filter of formula (I)

[0016]

[0017] The amount of branched saturated C15-C19 alkanes in the mixture of branched and straight-chain saturated C15-C19 alkanes is greater than 80% by weight, preferably greater than 90% by weight, and most preferably greater than 92% by weight.

[0018] For clarity, some terms used in this document are defined as follows:

[0019] In this document, "C x -C y "Alkanes" are alkane containing x to y carbon atoms; that is, for example, C15-C19 alkanes are alkanes containing 15 to 19 carbon atoms. Alkanes can be straight-chain or branched (i.e., not straight-chain) and are purely saturated hydrocarbons. For example, those with the molecular formula C 15 H 32 C 16 H 34 C 17 H 36 C 18 H 38 and C 19 H 40 All alkanes, such as pentadecane, octadecane, nonadecanane, 2,6,10,14-tetramethylpentadecanane, and isohexadecanane, are considered C15-C19 alkanes. Particularly preferred branched alkanes are those having only methyl groups as side chains, such as 2,6,10,14-tetramethylpentadecanane, 2-methylpentadecanane, or 3-methylpentadecanane.

[0020] In cases where the same notation for a symbol or group exists in several formulas, the definition of the group or symbol made in the context of a particular formula in this document also applies to other formulas containing the same notation.

[0021] In this document, the term "UV filter" refers to a substance that absorbs ultraviolet light (=UV light), which is electromagnetic radiation with wavelengths between 280 nm and 400 nm. A UV(A) filter is a UV filter that absorbs UV(A) light, which is electromagnetic radiation with wavelengths between 315 nm and 400 nm. A UV(B) filter is a UV filter that absorbs UV(B) light, which is electromagnetic radiation with wavelengths between 280 nm and 315 nm.

[0022] Liquid organic UV filters are liquid at ambient temperature (i.e., 25°C).

[0023] Solid organic UV filters are solid at ambient temperature (i.e., 25°C).

[0024] The term “solubilize / solubilization” in this document describes the property that the UV filter of formula (I) is incorporated into the composition in a manner that the UV filter does not precipitate or separate from the cosmetic composition at ambient temperature.

[0025] In this document, "a mixture of branched and straight-chain saturated C15-C19 alkanes" means that the mixture contains different alkanes, each of which has only 15, 16, 17, 18, or 19 carbon atoms, but does not contain any alkanes with fewer carbon atoms. Therefore, this mixture does not contain, for example, dodecane or isododecane. The mixture contains both branched and straight-chain C15-C19 alkanes.

[0026] UV filter of formula (I)

[0027] The cosmetic composition comprises a UV filter of formula (I).

[0028]

[0029] The UV filter of formula (I) (CAS: [302776-68-7]) is a crystalline solid with a melting point of 54°C, also known as diethylaminohydroxybenzoyl benzoate (INCI). This UV filter is a highly efficient UV(A) filter with a relatively broad absorption range, with a maximum absorption of 354 nm. It can be marketed, for example, under a trademark... A Plus was purchased from BASF.

[0030] Due to its polarity, it is highly soluble in esters, especially ethylhexyl benzoate and ethanol, but insoluble in water and alkanes.

[0031] Fatty acid and dextrin esters

[0032] The cosmetic composition further comprises esters of fatty acids and dextrin.

[0033] Dextrin is an oligomer of D-glucose. Its structure can be simplified as follows.

[0034]

[0035] Dextrins have different average degrees of sugar polymerization, which results in different molecular weights.

[0036] In this invention, the average degree of polymerization of the fatty acid and dextrin esters is preferably between 3 and 20, particularly between 8 and 16.

[0037] Preferably, the fatty acid in the ester of the fatty acid and dextrin is a C14-C18 fatty acid, especially a straight-chain C14-C18 fatty acid, and most preferably palmitic acid.

[0038] Dextrin palmitate is a particularly suitable ester for fatty acids and dextrin, such as that derived from Chiba Flour Milling. KL2 commercialization.

[0039] Dextrin has several esterifiable hydroxyl groups.

[0040] Preferably, the average number of esterified hydroxyl groups of the fatty acid and dextrin ester is greater than 2.5 per glucose unit, more preferably between 2.7 and 3.5, more preferably between 28 and 3.4, and most preferably between 2.8 and 3.2.

[0041] In one embodiment, the average number of esterified hydroxyl groups of the fatty acid and dextrin ester is greater than 3 per glucose unit, preferably between 3.05 and 3.5, more preferably between 3.1 and 3.4, and most preferably between 3.1 and 3.2.

[0042] In other words, preferably, almost all the hydroxyl groups of the dextrin are esterified.

[0043] More preferably, the molecular weight M of the fatty acid and dextrin ester is... n The value is between 8,000 Da and 16,000 Da, preferably between 9,000 Da and 13,000 Da, and more preferably between 10,000 Da and 11,500 Da.

[0044] Molecular weight Mn is expressed in Daltons (Da), and is determined by SEC / GPC, particularly using polystyrene as a standard.

[0045] Both fatty acids and dextrins have biological origins. Biological origins of chemicals are highly advantageous because such materials or their products are highly sustainable. There is significant market demand for highly sustainable products or compositions.

[0046] A mixture of branched and straight-chain saturated C15-C19 alkanes

[0047] The cosmetic composition comprises a mixture of branched and straight-chain saturated C15-C19 alkanes.

[0048] Particularly suitable mixtures of C15-C19 alkanes, especially those disclosed in WO 2016 / 185046, WO 2017 / 046177, WO2018 / 109353 A1, WO 2018 / 109354 A1 and WO 2018 / 172228A1.

[0049] Preferably, the mixture of branched and straight-chain saturated C15-C19 alkanes has a bio-source carbon content greater than or equal to 90% relative to the total weight of the mixture. The bio-source nature of the chemicals is highly advantageous because such materials are highly sustainable. There is significant market demand for highly sustainable products or compositions.

[0050] The determination of biomaterial content or biocarbon content is given according to standards ASTM D 6866-12, Method B (ASTM D6866-06), and ASTM D 7026 (ASTM D 7026-04). Standard ASTM D 6866 pertains to "Determination of bio-based content in natural materials using radiocarbon and isotope ratio mass spectrometry," while standard ASTM D 7026 pertains to "Sampling and reporting of results from determination of bio-based content in materials by carbon isotope analysis." The second standard refers to the first standard in its first paragraph. The first standard describes the sample... 14 C / 12 The C-ratio was measured and compared with a 100% renewable source reference for the sample. 14 C / 12 The C ratio is compared to give the relative percentage of C from regenerable sources in the sample. This standard is based on... 14 The same concept as C-division dating.

[0051] More preferably, the composition contains little or no aromatic hydrocarbons relative to the total weight of the mixture of branched and straight-chain saturated C15-C19 alkanes (less than 100 ppm, particularly less than 30 ppm).

[0052] A mixture of branched and straight-chain saturated C15-C19 alkanes is produced, in particular, by catalytic hydrogenation of hydrocarbon biomass feedstocks, such as that described in detail in WO 2016 / 185046, especially the one disclosed as Example 3 of WO 2016 / 185046.

[0053] Preferably, in the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is less than 10% by weight, more preferably less than 8% by weight, and most preferably greater than 5% by weight.

[0054] More preferably, the amount of C15 is less than 3% by weight, particularly less than 1% by weight, and preferably less than 0.05% by weight, relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0055] Preferably, the mixture of branched and straight-chain saturated C15-C19 alkanes is a mixture of branched and straight-chain saturated C16-C19 alkanes.

[0056] More preferably, the amount of branched saturated C16-C18 alkanes is greater than 90% by weight, and preferably greater than 95% by weight, relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0057] More preferably, the amount of C15 alkanes is less than 5% by weight, and particularly less than 2% by weight, relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0058] More preferably, the amount of branched saturated C17-C18 alkanes is greater than 85% by weight, and preferably greater than 92% by weight, relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0059] More preferably, the amount of C17 alkanes is between 15% and 20% by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0060] More preferably, the amount of branched saturated C18 alkanes is greater than 50% by weight, preferably greater than 60% by weight, and even more preferably greater than 70% by weight, relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0061] More preferably, the amount of C18 alkanes is particularly between 70% and 75% by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

[0062] In other words, the mixture of branched and straight-chain saturated C15-C19 alkanes is preferably composed mainly of C18 alkanes, and most preferably mainly of branched C18 alkanes.

[0063] Because the cosmetic composition contains a mixture of branched and straight-chain saturated C15-C19 alkanes, the composition does not contain any lower alkanes, specifically not any C12 alkanes and especially not any C12, C13, or C14 alkanes.

[0064] Further preferably, the mixture of C15-C19 alkanes has a viscosity of 3-15 mPa·s at 20°C, particularly between 6 mPa·s and 12 mPa·s.

[0065] Further preferably, the refractive index of the mixture of C15-C19 alkanes at 20°C is between 1.40 and 1.48, particularly between 1.42 and 1.45, and most preferably between 1.43 and 1.44.

[0066] Further preferably, the mixture of C15-C19 alkanes is made from SEPPIC as emogelene. TM L19 is a commercially available mixture of C15-C19 alkanes.

[0067] In the composition, the weight ratio of the fatty acid to the ester of dextrin to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is preferably less than 100% by weight, preferably in the range of 50-80% by weight, and most preferably in the range of 60-70% by weight.

[0068] In other words, the composition preferably contains more C15-C19 alkanes by weight than fatty acids and dextrin esters.

[0069] Furthermore, in the composition, the weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is preferably 100:1 to 1:100, preferably 80:1 to 1:100, more preferably 70:1 to 1:20, and most preferably 60:1 to 1:10.

[0070] Furthermore, it is preferred that the composition is in gel form.

[0071] Preferably, the viscosity of the cosmetic composition, measured on a TA Instruments AR550 rheometer using a 40 mm plate and a shear rate of 10 / s at 25°C, is greater than 1,000 mPa·s, more preferably greater than 5,000 mPa·s. More preferably, the viscosity is less than 100,000 mPa·s, more preferably less than 50,000 mPa·s, and even more preferably less than 40,000 mPa·s.

[0072] The sun protection factor (SPF) of the composition is preferably 10 or higher, preferably 20 or higher, more preferably 30 or higher, and even more preferably 50 or higher.

[0073] Preferably, the mixture of branched and straight-chain saturated C15-C19 alkanes and the mixture of fatty acids and dextrins are all based on organic sources.

[0074] Further preferably, according to OECD 301B, the mixture of branched and straight-chain saturated C15-C19 alkanes and the mixture of fatty acids and esters of dextrin are biodegradable.

[0075] The cosmetic composition may further include other organic or inorganic UV filters known to those skilled in the art of cosmetics and sun protection.

[0076] The cosmetic composition typically contains other ingredients suitable for use in the cosmetic composition.

[0077] In all embodiments of the present invention, the preferred cosmetic composition comprises water and is in the form of an emulsion.

[0078] Emulsions particularly contain an oil phase and an aqueous phase, such as, in particular, O / W, W / O, Si / W, W / Si, O / W / O, W / O / W multi- or Pickering emulsions.

[0079] The total amount of oil phase present in such emulsions is preferably at least 10% by weight based on the total weight of the cosmetic composition, for example, in the range of 10% to 60% by weight, preferably in the range of 15% to 50% by weight, and most preferably in the range of 15% to 40% by weight.

[0080] The amount of aqueous phase present in such emulsions is based on the total weight of the cosmetic composition, preferably at least 20% by weight, for example in the range of 40% to 90% by weight, preferably in the range of 50% to 85% by weight, and most preferably in the range of 60% to 85% by weight.

[0081] More preferably, the cosmetic composition is in the form of an oil-in-water (O / W) emulsion, wherein the O / W emulsion comprises an oil phase dispersed in an aqueous phase in the presence of an O / W emulsifier or a Si / W emulsifier. The preparation of such O / W emulsions is well known to those skilled in the art.

[0082] The composition in O / W emulsion form is preferably available, for example, in all formulations of O / W emulsions, such as serums, emulsions, or creams, and is prepared according to commonly used methods. The composition is preferably intended for topical application and can specifically constitute a dermatological or cosmetic composition intended, for example, for protecting human skin from the adverse effects of ultraviolet radiation (anti-wrinkle, anti-aging, moisturizing, sun protection, etc.).

[0083] The cosmetic composition further preferably comprises at least one emulsifier, preferably an anionic emulsifier. Preferably, the anionic emulsifier is an anionic emulsifier selected from the group consisting of: potassium cetyl phosphate, disodium cetearyl sulfosuccinate, sodium stearoyl glutamate, sodium stearoyl lactylate, glyceryl stearate citrate, and sodium cocoyl hydroxyethyl sulfonate.

[0084] In an advantageous embodiment, the cosmetic composition further comprises a phosphate ester emulsifier. Among preferred phosphate ester emulsifiers is C... 8-10 Alkyl ethyl phosphate, C 9-15 Alkyl phosphate, cetearyl alcohol polyether-2 phosphate, cetearyl alcohol polyether-5 phosphate, cetearyl alcohol polyether-8 phosphate, cetearyl alcohol polyether-10 phosphate, cetearyl phosphate, C6-10 alkanol polyether-4 phosphate, C 12-15 Alkyl alcohol polyether-2-phosphate, C 12-15 Alkyl alcohol polyether-3 phosphate, DEA-cetearyl alcohol polyether-2 phosphate, DEA-cetyl phosphate, DEA-oleyl alcohol polyether-3 phosphate, cetyl phosphate potassium, decanol polyether-4 phosphate, decanol polyether-6 phosphate, and lauryl alcohol polyether-4 phosphate. Specifically, cetyl phosphate potassium is used as an emulsifier, for example, it can be used as... K was purchased from Kaiseraugst, DSM Nutritional Products Ltd.

[0085] The cosmetic composition may also contain a nonionic emulsifier.

[0086] Examples of nonionic emulsifiers include condensation products of aliphatic (C8-C18) primary or secondary straight-chain or branched alcohols with alkyl oxides (typically ethylene oxide and typically having 6 to 30 ethylene oxide groups). Other representative nonionic emulsifiers include monoalkyl or dialkyl alkanolamides, such as cocoyl monoethanolamide or cocoyl diethanolamide and cocoyl monoisopropanolamide. Other nonionic emulsifiers that may be included are alkyl polyglycosides (APGs). Typically, an APG is an APG containing an alkyl group linked (optionally via a bridging group) to a block having one or more sugar groups, such as Oramix from Seppic. TMNS 1O; from BASF 818UP 1200 and 2000.

[0087] If the cosmetic composition is an O / W emulsion, it preferably contains at least one O / W or Si / W emulsifier selected from the following list: PEG-30 dihydroxystearate, PEG-4 dilaurate, PEG-8 dioleate, PEG-40 sorbitan peroleate, PEG-7 glyceryl cocoate, PEG-20 amygdalin glyceryl ester, PEG-25 hydrogenated castor oil, glyceryl stearate (and) PEG-100 stearate, PEG-7 palmitate, PEG-8 oleate, PEG-8 laurate, PEG-60 amygdalin glyceryl ester, PEG-20 methylglucose sesquistearate, PEG-40 stearate, PEG- 100 stearate, PEG-80 sorbitan lauryl ester, stearyl alcohol polyether-2, stearyl alcohol polyether-12, oleyl alcohol polyether-2, cetyl alcohol polyether-2, lauryl alcohol polyether-4, oleyl alcohol polyether-10, oleyl alcohol polyether-10 / polyethylene glycol 10 oleyl ether, cetyl alcohol polyether-10, isostearyl alcohol polyether-20, cetyl stearyl alcohol polyether-20, oleyl alcohol polyether-20, stearyl alcohol polyether-20, stearyl alcohol polyether-21, cetyl alcohol polyether-20, isocetyl alcohol polyether-20, lauryl alcohol polyether-23, stearyl alcohol polyether-100, glyceryl stearate citrate, glyceryl stearate (self-emulsifying), stearic acid, salts of stearic acid, polyglycerol-3-methylglucose distearate. Other suitable emulsifiers include sorbitol oleate, sorbitol sesquioleate, sorbitol isostearate, sorbitol trioleate, lauryl glucoside, decyl glucoside, sodium stearoyl glutamate, sucrose polystearate, and hydrated polyisobutylene.

[0088] In addition, one or more synthetic polymers can be used as emulsifiers. Examples include PVP eicosene copolymers, acrylates / C... 10-30 Alkyl acrylate crosspolymers, acrylate / stearyl alcohol polyether-20 methacrylate copolymers, PEG-22 / dodecyl glycol copolymers, PEG-45 / dodecyl glycol copolymers, and mixtures thereof.

[0089] Another particularly suitable class of O / W emulsifiers is nonionic self-emulsifying systems derived from olive oil, such as olive oil cetyl ester and dehydrated sorbitan olive oil ester (chemical composition: dehydrated sorbitan ester and cetearyl ester of olive oil fatty acids) sold under the trade name OLIVEM 1000.

[0090] Another suitable option is a commercially available polymer emulsifier, such as hydrophobically modified polyacrylic acid, for example, acrylate / C10-30 alkyl acrylate crosspolymers, which are marketed under trade names. TR-1 and TR-2 are commercially available from Noveon.

[0091] Another particularly suitable class of emulsifiers are polyglycerol esters or fatty acid diesters, also known as polyglycerol esters / diesters (i.e., polymers in which one or more fatty acids are combined with polyglycerol through esterification), for example, commercially available in Evonik as Isolan GPS [INCI name: polyglycerol-4 diisostearate / polyhydroxystearate / sebacate (i.e., diester of a mixture of isostearic acid, polyhydroxystearate and sebacate with polyglycerol-4)], or commercially available in Cognis as Dehymuls PGPH (INCI polyglycerol-2-2 dihydroxystearate).

[0092] Also suitable are polyalkylene glycol ethers, such as Brij 72 (polyoxyethylene (2) stearyl ether) or Brij 721 (polyoxyethylene (21) stearyl ether, for example, available at Croda).

[0093] The at least one O / W or Si / W type emulsifier is preferably used in an amount of 0.5 wt% to 10 wt% based on the total weight of the composition, for example, particularly in the range of 0.5 wt% to 5 wt%, for example, most particularly in the range of 0.5 wt% to 4 wt%.

[0094] Suitable W / O or W / Si emulsifiers include: polyglycerol-2-dihydroxystearate, PEG-30 dihydroxystearate, cetyl polydimethylsiloxane copolyol, polyglycerol-3-diisostearate of oleic acid / isostearic acid, polyglycerol-6-hexaricinolate, polyglycerol-4-oleate, polyglycerol-4-oleate / PEG-8 propylene glycol cocoate, magnesium stearate, sodium stearate, potassium laurate, potassium ricinoleate, sodium cocoate, sodium tallow, potassium castorate, sodium oleate, and mixtures thereof. Other suitable W / Si emulsifiers are lauryl polyglycerol-3, polydimethylsiloxane-ethyl dimethylpolysiloxane and / or PEG-9 polydimethylsiloxane-ethyl dimethylpolysiloxane and / or cetyl PEG / PPG-10 / 1 dimethylpolysiloxane and / or PEG-12 dimethylpolysiloxane crosspolymer and / or PEG / PPG-18 / 18 dimethylpolysiloxane. The at least one W / O emulsifier is preferably used in an amount of about 0.001% to 10% by weight, more preferably 0.2% to 7% by weight, relative to the total weight of the composition.

[0095] Furthermore, the cosmetic compositions according to the invention preferably advantageously contain at least one co-surfactant, for example selected from the group consisting of monoglycerides and diglycerides and / or fatty alcohols. The co-surfactant is typically used in an amount selected from the total weight of the composition, ranging from 0.1% to 10% by weight, particularly from 0.5% to 6% by weight, and most particularly from 1% to 5% by weight. Particularly suitable co-surfactants are selected from the following list: alkyl alcohols, such as cetyl alcohol (Lorol C16, Lanette 16), cetearyl alcohol (Lanette O), stearyl alcohol (Lanette 18), behenyl alcohol (Lanette 22), glyceryl stearate, glyceryl myristate (Estol 3650), hydrogenated coconut oil glyceride (Lipocire Na10), and mixtures thereof.

[0096] Based on the total weight of the cosmetic composition, the amount of emulsifier is preferably between 0.1 and 6.0% by weight, more preferably between 0.25 and 5.0% by weight, and particularly in the range of 0.5 and 4.0% by weight.

[0097] The composition is preferably sulfate-free.

[0098] Therefore, the cosmetic composition is preferably free of sulfates consisting of the group consisting of alkyl sulfates, alkyl ether sulfates, alkyl amide ether sulfates, alkylaryl polyether sulfates, and monoglyceride sulfates, as well as mixtures thereof.

[0099] As used herein, the term "free of," such as in "sulfate-free," means that the corresponding substance is present only in an amount less than 0.5% by weight, particularly less than 0.1% by weight, and even more particularly less than 0.05% by weight, relative to the weight of the composition. Preferably, "free of" means that the corresponding substance is completely absent from the composition.

[0100] The term "sulfate-free" as used in this document means that the composition does not contain any anionic surfactants having terminal anionic groups having the following formula.

[0101]

[0102] The cosmetic composition is preferably free of cationic emulsifiers. Typical examples of such cationic emulsifiers are isostearamidopropyl dimethylamine, silachlor, stearamidoethyl diethylamine, behenyltrimethylammonium sulfate, behenyloxyPG-trimethylammonium chloride, hexadecyltrimethylammonium bromide, behenamidopropyl dimethylamine behenate, rapeseed oil behenamidopropyl dimethylamine, stearamidopropyl dimethylamine stearate, cocamidopropyl PG-dimethylammonium chloride, distearyl ethyl hydroxyethyl methyl ammonium methyl sulfate, discocoyl ethyl hydroxyethyl methyl ammonium methyl sulfate, stearyl... Acylethyl dimethyl ammonium chloride, aramidopropyl trimethyl ammonium chloride, behenamidopropyl dimethylamine, brassinolide isoleucine ester ethanesulfonate, acrylamidopropyl trimethyl ammonium chloride / acrylate copolymer, linoleamide propyl ethyl dimethyl ammonium ethyl sulfate, dimethyl laurylamine isostearate, isostearamide propyl lauryl acetyl dimethyl ammonium chloride, especially behenyl trimethyl ammonium chloride, diceryl dimethyl ammonium chloride, cetrimonium chloride, stearyl trimethyl ammonium chloride and palmitamide propyl trimethyl ammonium chloride.

[0103] The cosmetic composition may preferably contain an additional UV filter. The additional UV filter may be solid or liquid. Preferably, the additional UV filter is a solid UV filter.

[0104] Suitable liquid organic UV filters absorb light in the UV(B) and / or UV(A) range and are liquid at ambient temperature (i.e., 25°C). Such liquid UV filters are well known to those skilled in the art and particularly include cinnamic acid esters, such as octyl methoxycinnamate (…). MCX) and isoamyl methoxycinnamate (Neo) E 1000); salicylate esters, such as homosalate (2-hydroxybenzoic acid 3,3,5-trimethylcyclohexyl ester, HMS) and ethylhexyl salicylate (also known as ethylhexyl salicylate, 2-hydroxybenzoic acid 2-ethylhexyl ester, ... EHS); acrylates, such as octocrylene (2-cyano-3,3-phenylacrylate 2-ethylhexyl ester, 340) and 2-cyano-3,3-diphenyl acrylate ethyl ester; esters of benzylidene malonate, such as, in particular, dialkyl benzylidene malonate esters, such as 4-methoxybenzyl malonate di(2-ethylhexyl) ester and polysiloxane-15 ( SLX); dialkyl esters of naphthalenecarboxylic acid, such as diethylhexyl 2,6-naphthalenecarboxylic acid (SLX); TQ); eugenol malonate, such as diethylhexyl eugenol malonate (TQ); ST liquid), and benzotriazolyl dodecyl p-cresol ( TL) as well as benzophenone-3 and cresoltrazol trisiloxane.

[0105] Particularly advantageous liquid organic UV filters are octyl methoxycinnamate, homosalate, ethylhexyl salicylate, octocrylene, diethylhexyl 2,6-naphthalenedicarboxylate, diethylhexyl syringite malonate, benzotriazolyl dodecyl p-cresol, benzophenone-3, cresoltrazol trisiloxane, and mixtures thereof.

[0106] In a preferred embodiment, the liquid UV filter is a liquid UV(B) filter selected from the group consisting of: ethylhexyl methoxycinnamate, octocrylene, humosalilate, ethylhexyl salicylate, benzophenone-3, and cresoltrazoltrisiloxane.

[0107] Suitable solid-state organic UV filters absorb light in the UV(B) and / or UV(A) range and are solid at ambient temperature (i.e., 25°C). Particularly suitable solid-state UV filters are selected from the group consisting of: bis(ethylhexyloxyphenol)methoxyphenyltriazine, butyl methoxydibenzoylmethane, methylene bis-benzotriazolyltetramethylbutylphenol, ethylhexyltriazinone, diethylhexylbutamidotriazinone, 4-methylbenzyl camphor, and 1,4-bis(benzoxazol-2'-yl)benzene.

[0108] Preferred solid organic UV(A) filters are UV(A) filters selected from the group consisting of: bis(ethylhexyloxyphenol)methoxyphenyltriazine, butyl methoxydibenzoylmethane, methylene bis-benzotriazolyltetramethylbutylphenol, and terphenyltriazine.

[0109] Preferred solid organic UV(B) filters are UV(B) filters selected from the group consisting of: diethylaminohydroxybenzoylhexylbenzoate ( T150), diethylhexylbutyramidotriazinone ( HEB) and 4-methylbenzyl camphor ( 5000).

[0110] The total amount of organic UV filters depends largely on the target UV protection.

[0111] Preferably, the amount of the solid organic UV filter, particularly the solid organic UV(A) filter, is selected from the range of 0.1 wt% to about 6 wt%, preferably from 0.5 wt% to 5 wt%, and most preferably from 1 wt% to 4 wt%.

[0112] Further preferably, the amount of the solid organic UV filter, particularly the solid organic UV(B) filter, is selected from the range of 0.1 wt% to about 6 wt%, preferably from 0.5 wt% to 5 wt%, and most preferably from 1 wt% to 4 wt%.

[0113] Even more preferably, the amount of the liquid organic UV filter, especially the liquid organic UV(B) filter, is selected from the range of 0.1 wt% to about 10 wt%, preferably from 0.5 wt% to 12 wt%, and most preferably from 1 wt% to 10 wt%.

[0114] The cosmetic composition may further include a cosmetic carrier, excipients, and diluents suitable for use in the cosmetic composition, as well as additives and active ingredients commonly used in the skin care industry, such as those described, for example, in the International Cosmetic Ingredient Dictionary & Handbook by Personal Care, available online at INFO BASE (http: / / online.personalcarecouncil.org / jsp / Home.jsp).

[0115] (http: / / www.personalcarecouncil.org / ), but not limited to this.

[0116] Such possible components of a cosmetic composition particularly enhance performance and / or consumer acceptability, such as preservatives, antioxidants, fatty substances / oils, thickeners, emollients, sunscreens, moisturizers, fragrances, co-surfactants, fillers, multivalent chelating agents, cationic, nonionic, or amphoteric polymers or mixtures thereof, acidifiers or alkalizers, viscosity modifiers, and natural hair nutrients (e.g., plant preparations, fruit extracts, sugar derivatives, and / or amino acids) or any other ingredient commonly formulated into a cosmetic composition. The necessary amounts of adjuvants and additives can be readily selected by those skilled in the art based on the desired product and will be illustrated in the examples, but are not limited thereto.

[0117] Particularly suitable thickeners in all embodiments are xanthan gum, gellan gum, and / or carboxymethyl cellulose. Most preferably in all embodiments, the thickener is xanthan gum or gellan gum.

[0118] Based on the total weight of the cosmetic composition, such thickeners are preferably used in an amount (total) selected from 0.1% by weight to 1% by weight, more preferably in an amount of 0.1% by weight to 0.5% by weight.

[0119] The cosmetic composition preferably has a pH in the range of 3 to 10, more preferably in the range of 4 to 8, and most preferably in the range of 4 to 7.5. The pH can be readily adjusted as needed using a suitable acid (e.g., citric acid) or base (e.g., NaOH) according to standard methods in the art.

[0120] The cosmetic composition is preferably free of sulfates and / or parabens and / or silicone oils and / or silicone surfactants.

[0121] The cosmetic composition is preferably a topical composition.

[0122] As used herein, the term "local" should be understood to mean externally applied to a keratinous substance, specifically skin, scalp, eyelashes, eyebrows, nails, mucous membranes, and hair, preferably skin.

[0123] Because topical compositions are intended for topical application, they are known to contain physiologically acceptable mediators, i.e., mediators compatible with keratinous substances such as skin, mucous membranes, and keratin fibers. Specifically, physiologically acceptable mediators are cosmetically acceptable carriers.

[0124] The term "cosmetically acceptable carrier" refers to all carriers and / or excipients and / or diluents routinely used in cosmetic compositions, particularly in sunscreen products.

[0125] Preferably, the cosmetic composition is a skin care preparation, a decorative preparation, or a functional preparation.

[0126] Examples of skin care products include, in particular, photoprotective products, anti-aging products, products for treating photoaging, body oils, body lotions, body gels, care creams, skin ointments, skin powders, moisturizing gels, moisturizing sprays, facial and / or body moisturizers, skin tanning products (i.e., compositions for artificial / non-sun tanning and / or browning of human skin), such as tanning creams, and skin brightening products.

[0127] Examples of functional preparations are cosmetic or pharmaceutical compositions containing active ingredients, such as, but not limited to, hormone preparations, vitamin preparations, plant extract preparations, and / or anti-aging preparations.

[0128] The cosmetic composition is preferably a skin care composition.

[0129] In the most preferred embodiment, the cosmetic composition is a sunscreen composition. The sunscreen composition is a photoprotective preparation (sunscreen product), such as sun protection milks, sunscreen lotions, sunscreen creams, sunscreen oils, sunscreen blocks, or day creams with an SPF (Sun Protection Factor). Sunscreen creams, sunscreen lotions, sunscreen milks, and sunscreen preparations are of particular interest.

[0130] Compared to corresponding cosmetic compositions that do not contain esters of the fatty acids and dextrins and do not contain a mixture of branched and straight-chain saturated C15-C19 alkanes, especially those that do not contain any silicone oils, the cosmetic compositions have improved sensory properties, particularly improved after-effects, and are able to dissolve higher amounts of the UV filter of formula (I).

[0131] It has been observed that the UV filter of formula (I) can be better solubilized in liquid saturated C8-C30 alkanes by adding fatty acid esters with dextrin.

[0132] Since both of these components are available from biological sources, it is possible to obtain this improvement in a sustainable manner, which is a major advantage of this invention.

[0133] Therefore, in another aspect, the present invention relates to the use of esters containing fatty acids and dextrin for increasing the solubility of solid organic UV filters in liquid saturated C8-C30 alkanes, particularly in branched and straight-chain saturated C15-C19 alkanes.

[0134] Liquid saturated C8-C30 alkanes are specifically selected from the group consisting of: C8-C30 mineral oils, decane, undecane, dodecane, hexadecane, octadecane, squalene (=2,6,10,15,19,23-hexamethyltetracosane), farnesane (=2,6,10-trimethyldodecane), dodecane, isopentadecane, isohexadecane, isooctadecane, isononadecane, and branched and straight-chain saturated C15-C19 alkanes, especially branched and straight-chain saturated C15-C19 alkanes as discussed in more detail above.

[0135] It has been observed that UV filters of formula (I) can be better solubilized in cosmetic compositions by combining them with mixtures of esters of fatty acids and dextrins, in particular, and branched and straight-chain saturated C15-C19 alkanes.

[0136] Therefore, in another aspect, the present invention relates to a UV filter of formula (I).

[0137]

[0138] A method for increasing the solubility of UV filters of formula (I) in cosmetic compositions by combining them with esters of fatty acids and dextrins, as well as a mixture of branched and straight-chain saturated C15-C19 alkanes.

[0139] Example

[0140] The present invention is further illustrated by the following experiments.

[0141] Solubilization of cosmetic compositions and diethylaminohydroxybenzoylhexylbenzoate

[0142] Preparation of premix

[0143] In Examples 1 and 2, dextrin palmitate was premixed with a portion of C15-C19 alkanes to form a premix (25% by weight of dextrin palmitate).

[0144] The premix was then mixed with the UV filter and the remaining C15-19 alkanes at 80°C using a magnetic stirrer, and cooled to 25°C without any stirring. After storing the solution at 25°C for one week, samples were pipetted from the bottom of the flask and observed under a microscope (Zeiss AX-10 microscope under polarized light, X100 magnification, Deltapix Invenio 5D camera). The photomicrographs are shown below. Figures 1 to 3 As shown.

[0145] Viscosity was measured on a TA Instruments AR550 rheometer using a 40 mm plate and a shear rate of 10 / s at 25°C.

[0146]

[0147] Table 1. Cosmetic compositions containing ethylaminohydroxybenzoylhexylbenzoate (as listed)

[0148] All ingredients are expressed in weight percent.

[0149] 1 Ethylaminohydroxybenzoylhexylbenzoate

[0150] 2 EMOGREEN TM L19

[0151] 3 KL2, Chiba Flour Milling

[0152] 4 Dextrin palmitate: M determined by SEC / GPC n =11,300-11,500Da.

[0153] 5 Polyurethane polymer (INCI Polyurethane-79) (30% Caprylic / Capric Triglyceride), Lubrizol

[0154] It has been shown that the UV filter cannot be dissolved in C15-19 alone (Reference 1) or in a polyurethane-based thickener (Reference 2). In both cases, UV filter crystals were found at the bottom of the flask (see [reference 2]). Figure 1 and Figure 3 ).

[0155] In the case of Example 1, the UV filter was solubilized very well and no crystals were observed (see Example 1). Figure 2 A gel was formed, and a viscosity greater than 8000 mPa·s was observed. A gel was also obtained in Comparative Example 2; however, the solubilizing effect of the UV filter was very low.

Claims

1. The use of fatty acid and dextrin esters for increasing the solubility of a solid organic UV filter in liquid saturated C8-C30 alkanes. The solid organic UV filter described herein is of formula (I): (I)， The liquid saturated C8-C30 alkanes therein are a mixture of branched and straight-chain saturated C15-C19 alkanes. The amount of branched saturated C15-C19 alkanes in the mixture of branched and straight-chain saturated C15-C19 alkanes is greater than 80% by weight. The fatty acids mentioned therein, and the fatty acids of the esters of dextrin, are straight-chain C14-C18 fatty acids.

2. The use according to claim 1, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of branched saturated C15-C19 alkanes is greater than 90% by weight.

3. The use according to claim 1, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of branched saturated C15-C19 alkanes is greater than 92% by weight.

4. The use according to claim 1, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is less than 10% by weight.

5. The use according to claim 1, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is less than 8% by weight.

6. The use according to claim 4 or 5, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is greater than 5% by weight.

7. The use according to claim 1, characterized in that, The amount of branched saturated C18 alkanes is greater than 50 by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

8. The use according to claim 1, characterized in that, The amount of branched saturated C18 alkanes is greater than 60 by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

9. The use according to claim 1, characterized in that, The amount of branched saturated C18 alkanes is greater than 70% by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

10. The use according to claim 1, characterized in that, The fatty acid in the fatty acid ester of dextrin is palmitic acid.

11. The use according to claim 1, characterized in that, The average degree of polymerization of the fatty acid and dextrin esters is between 3 and 20.

12. The use according to claim 1, characterized in that, The average degree of polymerization of the fatty acid and dextrin esters is between 8 and 16.

13. The use according to claim 1, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is greater than 3 per glucose unit.

14. The use according to claim 1, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is between 3.05 and 3.5 per glucose unit.

15. The use according to claim 1, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is between 3.1 and 3.4 per glucose unit.

16. The use according to claim 1, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is between 3.1 and 3.2 per glucose unit.

17. The use according to claim 1, characterized in that, The molecular weight M of the fatty acid and dextrin ester n Between 8,000 Da and 16,000 Da.

18. The use according to claim 1, characterized in that, The molecular weight M of the fatty acid and dextrin ester n Between 9,000 Da and 13,000 Da.

19. The use according to claim 1, characterized in that, The molecular weight M of the fatty acid and dextrin ester n Between 10,000 Da and 11,500 Da.

20. The use according to claim 1, characterized in that, The weight ratio of the fatty acid to dextrin ester to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is less than 100 by weight.

21. The use according to claim 1, characterized in that, The weight ratio of the fatty acid to dextrin ester to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is in the range of 50-80% by weight.

22. The use according to claim 1, characterized in that, The weight ratio of the fatty acid to dextrin ester to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is in the range of 60-70% by weight.

23. The use according to claim 1, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 100:1 to 1:

100.

24. The use according to claim 1, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 80:1 to 1:

100.

25. The use according to claim 1, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 70:1 to 1:

20.

26. The use according to claim 1, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 60:1 to 1:

10.

27. The use according to claim 1, characterized in that, The composition contains water and is in emulsion form.

28. The use according to claim 1, characterized in that, The composition is in gel form.

29. A UV filter of formula (I) A method for increasing the solubility of the UV filter of formula (I) in a cosmetic composition by combining it with esters of fatty acids and dextrins, as well as a mixture of branched and straight-chain saturated C15-C19 alkanes. In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of branched saturated C15-C19 alkanes is greater than 80% by weight. The fatty acids mentioned therein, and the fatty acids of the esters of dextrin, are straight-chain C14-C18 fatty acids.

30. The method according to claim 29, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of branched saturated C15-C19 alkanes is greater than 90% by weight.

31. The method according to claim 29, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of branched saturated C15-C19 alkanes is greater than 92% by weight.

32. The method according to claim 29, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is less than 10% by weight.

33. The method according to claim 29, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is less than 8% by weight.

34. The method according to claim 32 or 33, characterized in that, In the mixture of branched and straight-chain saturated C15-C19 alkanes, the amount of straight-chain saturated C15-C19 alkanes is greater than 5% by weight.

35. The method according to claim 29, characterized in that, The amount of branched saturated C18 alkanes is greater than 50 by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

36. The method according to claim 29, characterized in that, The amount of branched saturated C18 alkanes is greater than 60 by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

37. The method according to claim 29, characterized in that, The amount of branched saturated C18 alkanes is greater than 70% by weight relative to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes.

38. The method according to claim 29, characterized in that, The fatty acid in the fatty acid ester of dextrin is palmitic acid.

39. The method according to claim 29, characterized in that, The average degree of polymerization of the fatty acid and dextrin esters is between 3 and 20.

40. The method according to claim 29, characterized in that, The average degree of polymerization of the fatty acid and dextrin esters is between 8 and 16.

41. The method according to claim 29, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is greater than 3 per glucose unit.

42. The method according to claim 29, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is between 3.05 and 3.5 per glucose unit.

43. The method according to claim 29, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is between 3.1 and 3.4 per glucose unit.

44. The method according to claim 29, characterized in that, The average number of esterified hydroxyl groups of the fatty acid and dextrin esters is between 3.1 and 3.2 per glucose unit.

45. The method according to claim 29, characterized in that, The molecular weight M of the fatty acid and dextrin ester n Between 8,000 Da and 16,000 Da.

46. ​​The method according to claim 29, characterized in that, The molecular weight M of the fatty acid and dextrin ester n Between 9,000 Da and 13,000 Da.

47. The method according to claim 29, characterized in that, The molecular weight M of the fatty acid and dextrin ester n Between 10,000 Da and 11,500 Da.

48. The method according to claim 29, characterized in that, The weight ratio of the fatty acid to dextrin ester to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is less than 100 by weight.

49. The method according to claim 29, characterized in that, The weight ratio of the fatty acid to dextrin ester to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is in the range of 50-80% by weight.

50. The method according to claim 29, characterized in that, The weight ratio of the fatty acid to dextrin ester to the weight of the mixture of branched and straight-chain saturated C15-C19 alkanes is in the range of 60-70% by weight.

51. The method according to claim 29, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 100:1 to 1:

100.

52. The method according to claim 29, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 80:1 to 1:

100.

53. The method according to claim 29, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 70:1 to 1:

20.

54. The method according to claim 29, characterized in that, The weight ratio of the UV filter of formula (I) to the fatty acid and dextrin ester is 60:1 to 1:

10.

55. The method according to claim 29, characterized in that, The composition contains water and is in emulsion form.

56. The method according to claim 29, characterized in that, The composition is in gel form.

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