Combinations of biodegradable esters with active ingredients

Abstract

The present invention lies in the field of cosmetics and provides novel compositions with esters that can serve as silicone replacers in cosmetic applications and for conveying an antioxidant effect of cosmetic compositions comprising at least one natural oil component. Furthermore, cosmetic preparations as well as uses of the esters for conveying an antioxidant effect of cosmetic compositions are provided.

Description

[0001] Eisenfiihr Speiser

[0002] Munich, 20 March 2026

[0003] Our Ref.: SM 7048-02WO SOE / HMS

[0004] Applicant: Symrise AG

[0005] Serial Number: Subsequent Application based on PCT / EP2025 / 057620

[0006] Symrise AG

[0007] MuhlenfeldstraBe 1, 37603 Holzminden, Germany

[0008] Combinations of biodegradable esters with active ingredients

[0009] The present invention lies in the field of cosmetics and provides novel compositions with esters that can for conveying an antioxidant effect comprising at least one natural oil component. Furthermore, cosmetic preparations as well as uses of the esters for conveying an antioxidant of cosmetic compositions are provided.

[0010] 5 Silicones are a versatile group of synthetic materials derived from silica and are extensively used in cosmetics and personal care products due to their unique properties that enhance formulation and performance. Common types of silicones include dimethicone, cyclomethicone, dimethiconol, amodimethicone, and silicone elastomers. Dimethicone is frequently used for its smooth application and skin 0 protection properties, forming a barrier that reduces water loss. Cyclomethicone, a volatile silicone, evaporates quickly, leaving a silky, non-greasy feel without residue. Dimethiconol offers conditioning benefits and is often found in hair care products, while amodimethicone adheres well to hair, providing conditioning and anti-frizz benefits. Silicone elastomers create a gel-like texture, used to thicken 5 products and provide a silky, powdery finish in skincare and makeup.

[0011] Silicones offer numerous benefits, such as smooth application, non-comedogenic properties, water resistance, barrier formation, lightweight feel, and improved texture. These properties make them ideal for use in various cosmetic products. Inmoisturizers, silicones help lock in moisture without feeling heavy or greasy. Primers benefit from silicones by creating a smooth base for makeup application, blurring imperfections, and prolonging the wear of foundation. In foundations, silicones enhance spreadability and provide a flawless finish. Sunscreens utilize silicones to improve water resistance and skin feel, while hair care products benefit from silicones like dimethicone and amodimethicone, which provide shine, reduce frizz, and improve manageability. Anti-aging products also use silicones to fill in fine lines and wrinkles, providing a temporary smoothing effect.

[0012] Despite these benefits, there are some considerations and controversies associated with silicones. Environmental concerns arise because silicones are not biodegradable, raising issues about their impact, particularly in aquatic environments. Additionally, with focus on a more sustainable industry, it is desired to have compounds with the same benefits and conditions as currently available silicones, but can be produced from a natural source. Currently used silicone substances are inorganic synthetic polymers and are not biodegradable.

[0013] Some natural esters are already described in the state of the art. The European patent EP 2323969 B1 describes natural esters being an esterification product from undecylenic acid and a vegetable-derived fatty alcohol. The patent furthermore describes the use of this compound as ingredient in cosmetic compositions as emollient and that the provided compounds have an improved spreadability. Other compounds that can be used as silicone alternatives are mentioned in Goussard, J. M. Aubry, V. Nardello-Rataj, Adv Colloid Interface Sci 2022, 304, 102679 “Biobased alternatives to volatile silicones: Relationships between chemical structure, physicochemical properties and functional performances" or M. C. Montiel et al., Eng Life Sci. 2019; 19, 370-388 “Biocatalytic solutions to cyclomethicones problem in cosmetics".

[0014] It is always a goal in developing cosmetic formulations to develop compositions having a high efficiency or improved effect of the ingredients. This means, that the weight percentages of the ingredients can be diminished in a composition exhibiting a strong efficiency. This could lead to decreased manufacturing costs and thus a higher economic efficacy.

[0015] It was thus the primary object of the present invention to provide new, efficient cosmetic compositions with silicone replacers that can be used for replacing non-biodegradable conventionally used silicones in cosmetics and hair care.The primary object of the present invention was solved by providing a cosmetic composition comprising

[0016] i) at least one ester of formula I

[0017] o

[0018]

[0019] wherein n is selected from 3 to 12, and

[0020] wherein R is selected from C3 to C12 saturated and unsaturated alkylgroups, which are branched in alpha-, beta- and / or gamma-position in relation to oxygen and wherein each branch individually is selected from methyl, ethyl or propyl, and

[0021] ii) at least one natural oil component.

[0022] Surprisingly, it was found in terms of the present invention that the cosmetic compositions comprising at least one ester of formula I was able to convey an antioxidative effect to a composition. Such cosmetic compositions exhibit a better antioxidative effect than compositions without the ester according for formula I. This is remarkable as the ester according to formula I is reported to not have antioxidant properties itself.

[0023] The compound according to the invention is an ester derived from an esterification or transesterification process of suitable acids or alcohols. Especially preferably, these compounds are derived from natural origin and not petrochemically derived.

[0024] The compounds according to formula I are esters which exhibit properties comparable to those of conventionally used, petrochemically derived silicones and therefore function as silicone substitutes. Accordingly, these compounds are herein referred to as “silicone replacers.” In the context of cosmetics, silicones (chemically known as polysiloxanes) are a group of synthetic ingredients based ona backbone of alternating silicon and oxygen atoms, combined with organic side groups. This structure gives them distinctive sensory and functional properties that are highly valued in personal care formulations. In particular, silicones form smooth, flexible films on the skin or hair, providing a silky, non-greasy feel, improving spreadability, and creating a soft-focus or conditioning effect. They are also valued for their ability to enhance water resistance, reduce tackiness, and protect surfaces without clogging pores or feeling heavy.

[0025] The compounds of formula I are further characterized in that they are not olfactorily active, i.e. they do not possess a perceptible intrinsic odor. Consequently, any compounds (e.g. geranyl acetate) that would otherwise fall within the scope of formula I but exhibit an odor are expressly excluded from the present invention.

[0026] Preferably, the esters according to formula I are non-petrochemically derived.

[0027] The terms “petrochemical” or “petrochemically derived” define the source of the educt as originating from natural gas and / or crude oil, i.e. from sources that are not sustainable and will be exhausted in the next few years. A “non-petrochemical” substance is therefore obtained from a natural and not a petrochemical source.

[0028] Methods for determining whether and what proportion of the carbon in a compound is petrochemically and / or non-petrochemically derived are known to the person skilled in the art.

[0029] In the context of the present invention, radiocarbon dating, e.g. according to the ASTM D6866-16 method, is preferably used. The method is based on the observation that the ratio of 12C and 14C is an indicator of non-petrochemical carbon content. Natural sources include renewable and therefore sustainable raw materials so that, in contrast to petrochemical sources, they are (theoretically) not finite but part of the biological carbon cycle.

[0030] Preferably, the at least one ester according to formula I has a natural carbon content of at least 70 %, preferably at least 75 %, preferably at least 80 %, preferably 85 %, further preferably at least 90 %, particularly preferably at least 95 %, further preferably at least 97.5 % and most preferably 100 % of non-petrochemical origin, based on the total carbon content of the respective compound, determined by radiocarbon dating. It is particularly preferred that the compounds according to the present invention are non-petrochemical, i.e. the totalcarbon of the respective compound is non-petrochemically derived carbon, based on the total carbon content of the respective compound as determined by radiocarbon dating.

[0031] Preferably, the at least one ester according to formula I is present in the composition in an amount of from 0.001 to 99.5 wt.-%, preferably in an amount of from 0.01 to 50 wt.-% and especially preferably in an amount of from 0.1 to 25 wt.-%, in relation to the total weight of the cosmetic composition. For example, the at least one compound of formula I is added to, or comprised in the cosmetic composition in an amount of 0.001 to 99.5 wt.-%, preferably 0.01 to 50 wt.-%, more preferably 0.1 to 25 wt.-%, based on the total weight of the formulation.

[0032] Preferably, at least one ester according to formula I is selected from the group consisting of 2-methylbutyl dodec-11 -enoate, isopentyl undec- 10-enoate (3-methylbutyl dodec- 11 -enoate), 2-methylbutyl undec-10-enoate, isobutyl undec-10-enoate, 2-ethylhexyl undec-10-enoate, sec-butyl undec- 10-enoate (1 -methylpropyl dodec- 11 -enoate), isopentyl undec-10-enoate (3-methyl butyl undec-10-enoate) octan-3-yl undec-10-enoate, isopentyl dec-9-enoate, 2-methylbutyl dec-9-enoate, isobutyl dec-9-enoate, 2-ethylhexyl dec-9-enoate, sec-butyl dec-9-enoate, octan-3-yl dec-9-enoate, isopentyl oct-7-enoate, 2-methylbutyl oct-7-enoate, isobutyl oct-7-enoate, 2-ethylhexyl oct-7-enoate, sec-butyl oct-7-enoate, octan-3-yl oct-7-enoate, isobutyl undec-10-enoate (2-methylpropyl undec- 10-enoate), isopentyl dec-9-enoate (3-methylbutyl dec-9-enoate), sec-butyl dec-9-enoate (1-methylpropyl dec-9-enoate), isopentyl hept-6-enoate (3-methylbutyl hept-6-enoate), 2-methylbutyl hept-6-enoate, isobutyl hept-6-enoate (2-methylpropyl hept-6-enoate) 2-ethylhexyl hept-6-enoate, octan-3-yl hept-6-enoate or a mixture thereof.

[0033] It is preferred in terms of the present invention that the at least one natural oil component is selected from the group consisting of caprylic / capric triglyceride, Argania Spinose kernel oil, Cannabis Sativa seed oil, Ricinus Communis (castor) seed oil, Crambe Abyssinica seed oil, Abies Alba Seed Oil, Acacia Victoriae Seed Oil, Actinidia Chinensis (Kiwi) Seed Oil, Amaranthus Hypochondriacus Seed Oil, Simmondsia Chinensis (Jojoba) Seed Oil, Arachis Hypogaea (Peanut) Oil, Astrocaryum Murumuru Seed Butter, Astrocaryum Tucuma Seed Butter, Astrocaryum Tucuma Seed Oil, Astrocaryum Vulgare Fruit Oil, Astrocaryum Vulgare Kernel Oil, Avena Sativa (Oat) Kernel Oil, Brassica Alba Seed Oil, Brassica Campestris (Rapeseed) Seed Oil, Butyrospermum Parkii (Shea) Oil,Butyrospermum Parkii (Shea) butter, Calendula Officinalis Seed Oil, Calophyllum Inophyllum Seed Oil, Calophyllum Tacamahaca Seed Oil, Camellia Oleifera Seed Oil, Camellia Reticulata Seed Oil, Camellia Sinensis Seed Oil, Cannabis Sativa Seed / Stem Oil, Canola Oil, Carthamus Tinctorius (Safflower) Seed Oil, Chlorella Vulgaris Oil, Citrullus Lanatus (Watermelon) Seed Oil, Citrus Aurantifolia (Lime) Seed Oil, Citrus Aurantium Dulcis (Orange) Seed Oil, Citrus Grandis (Grapefruit) Seed Oil, Cocos Nucifera (Coconut) Oil, Cocos Nucifera (Coconut) Seed Butter, Coffea Arabica (Coffee) Seed Oil, Chlorella Oil (biotech), Corylus Americana (Hazelnut) Seed Oil, Corylus Avellana (Hazelnut) Seed Oil, Cucumis Melo (Melon) Seed Oil, Cucumis Sativus (Cucumber) Seed Oil, Cucurbita Pepo (Pumpkin) Seed Oil, Elaeis Guineensis (Palm) Oil, Elaeis (Palm) Fruit Oil, Glycine Soja (Soybean) Oil, Gossypium Herbaceum (Cotton) Seed Oil, Gossypium Hirsutum (Cotton) Seed Oil, Helianthus Annuus (Sunflower) Seed Oil, Macadamia Integrifolia Seed Oil, Macadamia Ternifolia Seed Oil, Mangifera Indica (Mango) Seed Butter, Mangifera Indica (Mango) Seed Oil, Melissa Officinalis Seed Oil, Microalgae Oil, Moringa Oleifera Seed Oil, Moringa Peregrina Seed Oil, Oenothera Biennis (Evening Primrose) Oil, Olea Europaea (Olive) Fruit Oil, Olus Oil, Orbignya Oleifera Seed Oil, Orbignya Speciosa Kernel Oil, Oryza Sativa (Rice) Bran / Germ Oil, Oryza Sativa (Rice) Bran Oil, Oryza Sativa (Rice) Germ Oil, Oryza Sativa (Rice) Lipids, Oryza Sativa (Rice) Seed Oil, Papaver Somniferum Seed Oil, Passiflora Edulis Seed Oil, Persea Gratissima (Avocado) Butter, Persea Gratissima (Avocado) Oil, Prunus Amygdalus Dulcis (Sweet Almond) Oil, Prunus Armeniaca (Apricot) Kernel Oil, Prunus Persica (Peach) Kernel Oil, Punica Granatum Seed Oil, Pyrus Malus (Apple) Seed Oil, Ricinoleic / Caproic / Caprylic / Capric Triglyceride(s), Rosa Canina Fruit Oil, Rosa Moschata Seed Oil, Rubus Idaeus (Raspberry) Seed Oil, Sesamum Indicum (Sesame) Seed Butter, Soybean Glycerides, Theobroma Cacao (Cocoa) Seed Butter, Theobroma Grandiflorum Seed Butter, Triticum Vulgare (Wheat) Bran Lipids, Triticum Vulgare (Wheat) Germ Oil, Vitis Vinifera (Grape) Seed Oil, Zea Mays (Corn) Germ Oil, and Zea Mays (Corn) Oil.

[0034] Especially preferably, the at least one natural oil component is selected from the group consisting of caprylic / capric triglyceride, Argania Spinose Kernel Oil, Ricinus Communis (castor) Seed Oil, Simmondsia Chinensis (Jojoba) Seed Oil, Butyrospermum Parkii (Shea) butter, Cocos Nucifera (Coconut) Oil, Glycine Soja (Soybean) Oil, Helianthus Annuus (Sunflower) Seed Oil, Olea Europaea (Olive) Fruit Oil, Persea Gratissima (Avocado) Oil, Prunus Amygdalus Dulcis (Sweet Almond) Oil, Theobroma Cacao (Cocoa) Seed Butter, Vitis Vinifera (Grape) Seed Oil.Preferably, the at least one natural oil component is present in the cosmetic composition in an amount of from 0.001 to 99.5 wt.-%, preferably in an amount of from 0.01 to 95 wt.-% and especially preferably in an amount of from 0.1 to 95 wt.-%, in relation to the total weight of the cosmetic composition.

[0035] Also preferred in terms of the present invention is that the at least one natural oil component is present in the cosmetic composition in an amount of from 0.001 to 50 wt.-%, preferably in an amount of from 0.01 to 40 wt.-% and especially preferably in an amount of from 0.1 to 30 wt.-%, in relation to the total weight of the cosmetic composition.

[0036] It is also preferred that the cosmetic composition according to the invention further comprises at least one antioxidant.

[0037] Thus, the present invention preferably also relates to a cosmetic composition comprising

[0038] i) at least one ester of formula I

[0039] o

[0040]

[0041] wherein n is selected from 3 to 12, and

[0042] wherein R is selected from C3 to C12 saturated and unsaturated alkylgroups, which are branched in alpha-, beta- and / or gamma-position in relation to oxygen and wherein each branch individually is selected from methyl, ethyl or propyl,

[0043] ii) at least one natural oil component, and

[0044] iii) at least an antioxidant

[0045] Surprisingly, it was found in terms of the present invention that the cosmetic composition comprising at least one ester of formula I and one natural oilcomponent and an antioxidant was able to convey an antioxidative effect to a composition. Ester of formula I can boost performance of common used antioxidants and can lead to prolong shelf life.

[0046] Preferably, the antioxidant is selected from the group consisting of vitamin E, ferulic acid, coenzyme Q10, resveratrol, green tea extract, niacinamide, glutathione, alpha-lipoic acid, polyphenols, astaxanthin, beta-carotene, rosemary extract, panthenol, dimethylmethoxy chromanol, 4-hydroxyacetophenone, ascorbic acid and its salts, hydroxymethoxyphenyl decanone, beta-aspartyl arginine, uric acid, urea, hydroxypinacolone retinoate, vitamin A and vitamin A derivatives, butylhydroxytoluol (BHT), butylhydroxyanisol (BHA), hydroxyphenyl propam idobenzoic acid, ascorbyl palmitate, ascorbyl phosphate and salts thereof, carnosine, rutin, tocopherol, tocopheryl acetate, ubiquinone-10, dilauryl thiodipropionate, pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, triethyl citrate, diethylhexyl syringylidene malonate, lactobacillus ferment, lactobacillus filtrate, lactobacillus lysate, cannabinoids, cannabidiol and its extracts, cannabinol, hydroxyphenyl propam idobenzoic acid, Zingiber Officinalis root extract, tropolone, allantoin, o-cymen-5-ol, sodium metabisulfite, phenylethyl resorcinol and mixtures of two or more of said antioxidants.

[0047] Especially preferably, the at least one antioxidant is selected from the group consisting tocopherols, preferably, wherein the at least one further antioxidant contains or consists of a-, y- and b-tocopherol or tocopherolacetate. With this group of substances, the compounds of formula (I) combine in an advantageous manner, resulting in a boosting effect of the antioxidative property of tocopherol or tocopherolacetatel.

[0048] Preferably, the at least one antioxidant is present in the composition in an amount of from 0.0001 to 10 wt.-%, preferably in an amount of from 0.0005 to 8 wt.-% and especially preferably in an amount of from 0.001 to 5 wt.-%, in relation to the total weight of the cosmetic composition.

[0049] It is preferred in terms of the present invention that the composition comprises at least one additional cosmetic component different from (i) or (ii), selected from the group consisting of antimicrobials, viscosity controlling agents and further cosmetically active substances.Such at least one additional compound is preferably selected from the group consisting of cosmetically active substances, preferably selected from the group consisting of abrasives, anti-acne agents and sebum reduction agents, anti-aging agents, antibacterial agents, anti-cellulite agents, anti-inflammatory agents, irritation-preventing agents, anti-irritants (anti-inflammatory, irritation-inhibiting and irritation-preventing agents), astringents, antiseptic agents, antistatic agents, binders, buffers, carriers, chelating agents, cell stimulants, cleansing agents, surface-active substances, deodorants and antiperspirants, enzymes, essential oils, fibers, film formers, fixers, foaming agents, foam stabilizers, antifoaming agents, foam boosters, fungicides, gelling agents and gel-forming, moisture regulators, osmolytes, compatible solutes, bleaching agents, optical brightening agents, impregnating agents, turbidity agents, opacifiers, brighteners, polymers, powders, proteins and protein hydrolysates, refattening agents, abrasive agents, skin soothing agents, skin cleansing agents, skin caring agents, skin repair agents, skin whitening agents, skin protecting agents, skin softening agents, skin cooling agents, benzylidene-beta-dicarbonyl compounds, alpha-benzoyl cinnamic acid nitriles, detergents, skin tanning agents, thickening agents, vitamins, oils, waxes and fats, phospholipids, fatty acids, surfactants, yeast extracts, extracts of algae or microalgae, electrolytes, liquefiers and organic solvents.

[0050] Viscosity controlling agents are preferably selected from the group consisting of xanthan gum, hydroxyethylcellulose, cellulose gum, cellulose, aluminium starch octenylsuccinate, hydroxypropyl methylcellulose, acacia Senegal gum, microcrystalline cellulose, sclerotium gum, carrageenan and salts, hydroxypropylcellulose, dextrin, algin, caesalpinia spinosa gum, sodium starch octenylsuccinate, galactoarabinan, hydroxypropyl guar, cyamopsis tetragonoloba gum, sodium polyacrylate starch, cetyl hydroxyethylcellulose, ethylcellulose, sodium carboxymethyl betaglucan, hydrolyzed corn starch octenylsuccinate, pistacia lentiscus gum, dehydroxanthan gum, pectin, acrylates / c10-30 alkyl acrylate crosspolymer, acrylates / beheneth-25 methacrylate copolymer; ammonium acryloyldimethyltaurate / vp copolymer, butylene / ethylene / styrene copolymer, carbomer, cera microcrystal I ina, chondrus crispus extract, corn starch modified, disteardimonium hectorite, glyceryl acrylate / acrylic acid copolymer, guar hydroxypropyltrimonium chloride, hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer, pvp, pentaerythrityl tetraethylhexanoate, phytosteryl / isostearyl / cetyl / stearyl / behenyl dimer dilinoleate, sodium acrylate / sodium acryloyldimethyl taurate copolymer, sodium acrylates copolymer,sodium polyacrlyate, stearalkonium bentonite, tapioaca starch, zea (mays) corn starch, gellan gum, and mixtures thereof.

[0051] Especially preferably, the viscosity controlling agent is selected from the group consisiting of xanthan gum, hydroxyethylcellulose, cellulose gum, cellulose, aluminium starch octenylsuccinate, hydroxypropyl methylcellulose, acacia Senegal gum, microcrystalline cellulose, sclerotium gum, carrageenan and salts, caesalpinia spinosa gum, hydroxypropyl guar, cyamopsis tetragonoloba gum, acrylates / c10-30 alkyl acrylate crosspolymer, carbomer, guar hydroxypropyltrimonium chloride, and tapioaca starch.

[0052] Antimicrobials are preferably selected from the group consisting of acidic antimicrobials, parabens or phenylhydroxyalkyl ethers. These antimicrobials act primarily against microorganisms, in particular bacteria, yeast and / or fungi, preferably, against microorganisms selected from the group consisting of Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Burkholderia cepacia, Candida albicans and Aspergillus brasiliensis, and combinations thereof. By suppressing or inhibiting the microorganisms’ growth, the degradation and deterioration of the formulation, in particular during storage, which sometimes goes along with impairment of the sensory quality of the products, can be prevented or at least minimized.

[0053] The antimicrobials may be selected from the group consisting of butyl paraben, 2-benzylheptanol, 4-hydroxyacetophenone, alkyl (c 12-22) trimethyl ammonium bromide and chloride, ascorbic acid and salts thereof, benzalkonium bromide, benzalkonium chloride, benzalkonium saccharinate, benzethonium chloride, benzyl alcohol, camphor, caprylhydroxamic acid, cetylpyridinium chloride, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, chlorocresol, chloroxylenol, chlorphenesin, cyclohexylglycerin, dehydroacetic acid, diazolidinyl urea, disodium edta, dmdm hydantoin, ethylhexylglycerin, ethylparabene, glycerin, glyceryl caprate, glyceryl caprylate, glyceryl heptanoate, hexamidine, hexamidine diisethionate, hexylglycerin, hydroxypropyl benzoate, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, lodopropynyl butylcarbamate, isobutylparaben, itaconic acid and salts thereof, lactic acid, methyl salicylate, methylchloroisothiazolinone, methylisothiazolinone, methylparaben and its salts, natamycin, nisin, phenethyl alcohol, phenoxyethanol, phenylpropanol, polyarginine, polylysine, potassium sorbate, propylparaben, silver chloride, silver citrate, sodium benzoate, sodiumethylparaben, sodium levulinate or levulinic acid and esters and / or ketals thereof, sodium propylparaben, sorbic acid, sorbitan caprylate, tea-salicylate, tetrasodium glutamate diacetate, triclocarban, trisodium ethylenediamine disuccinate, zinc citrate, trisodium dicarboxym ethyl alaninate, 1,3-propanediol, 1,2-pentanediol, 1.2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 2.3-pentanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2.3-nonanediol, and mixtures of two or more the aforesaid compounds.

[0054] Preferably, the antimicrobial agent is selected from the group consisting of 4-hydroxyacetophenone, benzyl alcohol, butyl paraben, caprylhydroxamic acid; chlorhexidine, chlorhexidine digluconate, chlorphenesin, diazolidinyl urea, disodium edta, dmdm hydantoin, ethylparaben, glyceryl caprate, glyceryl caprylate, glyceryl laurate, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, lodopropynyl butylcarbamate, isobutylparaben, itaconic acid, methylchloroisothiazolinone, methylisothiazolinone, methylparaben, phenethyl alcohol, phenoxyethanol, potassium sorbate, propylparaben, sodium benzoate, sodium ethylparaben, sodium propylparaben, sorbitan caprylate, tea-salicylate, tetrasodium glutamate diacetate, trisodium ethylenediamine disuccinate, dehydroacetic acid, 1,3-propanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, and mixtures of two or more the aforesaid compounds.

[0055] Especially preferably, the antimicrobial agent is selected from the group consisting of 4-hydroxyacetophenone, benzyl alcohol, butylparaben, caprylhydroxamic acid, disodium edta, dmdm hydantoin, ethylparaben, ethylhexylglycerin, glyceryl caprylate, glyceryl heptanoate, hydroxypropyl benzoate, hydroxyethoxyphenyl butanol, hydroxyethoxyphenyl butanone, itaconic acid, methylchloroisothiazolinone, methylisothiazolinone, methylparaben, natamycin, nisin, phenoxyethanol, potassium sorbate, propylparaben, sodium benzoate, sodium propylparaben, dehydroacetic acid, 1,3- propanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, and mixtures of two or more the aforesaid compounds.

[0056] The above mentioned antimicrobial agents can be used either as a single component or in combination with one or more other antimicrobial agents. In orderto enhance the antimicrobial effect and to cover a broader range of antimicrobial effect, a combination of two or more antimicrobial agents is preferably used.

[0057] It is also preferred in terms of the cosmetic composition according to the invention that R is selected from a C3 to C8 alkyl group, which is preferably branched and wherein each branch is individually selected from methyl or ethyl.

[0058] Furthermore, it is preferred that the branched alkyl group is branched in alpha, beta and / or gamma position in relation to oxygen.

[0059] The branching nomenclature refers to the carbon atoms starting from the oxygen of the compound according to formula (I). The positions referring to the corresponding branches are depicted in formula II exemplarily.

[0060] Especially preferably, the at least one ester of formula I is at least one ester of formula II

[0061]

[0062] For obtaining an ester according to formula II, undecylenic acid may be used as educt, which is derived from castor oil. Castor oil is a vegetable oil pressed from castor beans and thus of natural origin.

[0063] Also, the present invention preferably relates to a cosmetic composition comprising at least one compound of formula (II) as well as at least one compound of formula (HI)

[0064]

[0065] (HI)It is preferred in terms of the cosmetic composition according to the present invention that the ratio between the at least one ester of formula I or formula II and the at least one antioxidant is 100:1 to 1:1, preferably 50:1 to 1:2.

[0066] This ratio means that the composition comprises a ratio of 100 parts of ester to 1 part of antioxidant to one part ester to one part antioxidant.

[0067] Preferably, if at least one antioxidant is present in the cosmetic composition, the at least one ester is present in a higher amount than the antioxidant.

[0068] It is preferred in terms of the cosmetic composition according to the present invention that the at least one antioxidant is present and the ratio between the at least one ester of formula I or formula II to antioxidant is 1:20 to 1:2.5, preferably 1:10 to 1:5.

[0069] Another aspect of the present invention relates to a preparation, preferably a cosmetic preparation, comprising the cosmetic composition according to the invention, preferably in an amount of from 0.001 to 99.5 wt.-%, preferably of from 0.01 to 50 wt.-%, especially preferable of from 0.05 to 20 wt.-% and moreover especially preferable of between 0.1 to 10 wt.-% depending on the total weight of the composition.

[0070] In such a preparation, the complete amount of the at least one ester, the at least one natural oil component and optionally the at least one antioxidant was part of a cosmetic composition used for manufacturing a final preparation.

[0071] It is preferred that the preparation according to the invention is selected from leave-on or rinse-off personal care products, preferably selected from the group consisting of shampoos, cleansing products, preferably shower gels, body washes and soaps, wet wipes, leave-on and rinse-off conditioners, hair butters and waxes, beard care and hair oils.

[0072] A “cosmetic composition” in terms of the present invention describes a semifinished product, which can be incorporated into a finished product, wherein a “cosmetic preparation” is a finished product, which can be used for direct application on the skin or the hair. Such a preparation could be in the form ofemulsions, milks, lotions, creams, balms, ointments, gels, tonics, serums, cleansers, granules, powders, stick preparations, leave-on styling products, foams, aerosols, concentrated and / or solid formulations or sprays.

[0073] Generally, the use of the ester of formula (I) is not limited to specific types of preparations. Preferred preparations, however, are in the form selected from the group consisting of dispersions, water free oil formulations, liquid surfactant formulations, solid surfactant formulations, micellar waters, and aqueous based solutions. It is further preferred that the dispersion is an emulsion, in particular an O / W emulsion, a W / O emulsion, a multiple emulsion, a hydrodispersion gel, a balm, a multiple emulsion of the water-in-oil type (W / O / W) or of the oil-in-water type (O / W / O), a PIT emulsion, a pickering emulsion, a micro-emulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, an oil based cream or a liposome based formulation. The aqueous based solution preferably includes aqueous, aqueous alcoholic and aqueous glycolic solutions.

[0074] Another aspect of the present invention relates to the use of at least one ester of formula (I)

[0075] o

[0076] n

[0077]

[0078] wherein n is selected from 3 to 12, and

[0079] wherein R is selected from C2 to C12 saturated and unsaturated alkylgroups, which are optionally branched in alpha-, beta- and / or gamma-position in relation to oxygen and wherein each branch is individually selected from methyl, ethyl or propyl,

[0080] for conveying an antioxidant effect to a natural oil component and / or boosting the antioxidative effect of at least one antioxidant in a cosmetic composition or cosmetic preparation.The term “conveying an antioxidative effect” refers to the ability of certain substances, known as antioxidants, to neutralize free radicals and reactive oxygen species (ROS) that can cause oxidative stress in compositions and preparations. This protective action helps prevent damage to cosmetic compositions. Antioxidants achieve this by donating electrons to unstable free radicals, effectively stabilizing them without becoming reactive themselves. This process reduces the overall oxidative burden.

[0081] The term “boosting the antioxidative effect” means further strengthening the antioxidative effect of an antioxidant in comparison to a composition without the ester according to formula I. The addition of an ester according to formula I or II improves the effect of the at least one antioxidant further and thus boosts the effect of the antioxidant in a composition.

[0082] It is preferred that the at least one ester is selected from the group consisting of isopentylundec-10-enoate, 2-methylbutyl undec-10-enoate, isobutyl-undec-10-enoate, 2-ethylhexyl undec-10-enoate, sec-butyl undec-10-enoate, heptyl undecylenate, isopentyldec-9-enoate and neopentyl glycol diheptonatoate and isododecane or mixtures thereof.

[0083] Especially preferably, the ester is an ester of formula II

[0084] o

[0085]

[0086] (II)

[0087] It is furthermore preferred that the ratio between the at least one ester of formula I and the at least one natural oil component is 1 : 100 to 1 : 1 , preferably 1 :50 to 1 :2.

[0088] It is also preferred that at least one antioxidant is present in the cosmetic composition or preparation and the ratio between the at least one ester of formula I or formula II to antioxidant is 20:1 to 2.5:1, preferably 10:1 to 5:1.

[0089] The present invention is now further characterized by illustrative, non-limiting examples.Examples

[0090] The following esters known as replacers for silicone were tested together with tocopherol or tocopherolacetate. The antioxidative potential was tested using the method “Oxipres”.

[0091] Table 1: Tested esters

[0092] III PAG / Name Structure

[0093] lsopentylundec-10-enoate

[0094] lsobutyl-undec-10-enoate [^2^2^

[0095] 2-ethylhexyl undec-10-enoate

[0096] Sec-butyl undec-10-enoate

[0097] Heptyl Undecylenate / LexFeel®

[0098] Natural

[0099] Neopentyl Glycol Diheptanoate &

[0100] Isododecane / LexFeel® D5

[0101]

[0102] Example 1 : Testing of antioxidative potential

[0103] The tests were performed using an Oxipres. The samples are treated for 48 hours at 80°C with 5 bar oxygen. The antioxidative potential was calculated based on the induction period, which is the time in h until the oxidation starts. Oxidation can be observed as result of a decreasing pressure. The protection factor is calculated in the following way:

[0104] Protection factor (PF)—IP(Sample) I I P(Sample Placebo)

[0105] In the context of Oxipres experiments, the IP value refers to the induction period (or induction time), which is a measure of the oxidative stability of a substance, such as an oil, fat, or cosmetic formulation.

[0106] The induction period is defined as the time interval during which the sample remains relatively resistant to oxidation under accelerated conditions. During this phase, oxidation reactions occur only at a very low rate. The end of the induction period is marked by a sudden increase in oxidation activity, which is detected inthe Oxipres apparatus as a noticeable drop in oxygen pressure due to rapid oxygen consumption.

[0107] A longer IP value indicates that the substance has a higher resistance to oxidative degradation and is therefore more stable over time. Conversely, a shorter IP value suggests lower oxidative stability and a greater tendency for the material to degrade, for example by becoming rancid or losing its functional properties.

[0108] Each sample was stirred for 15 minutes at RT with a magnetic stirrer (250rpm).

[0109] 15 g of the sample is then transferred to Oxipres and treated as described. 15 g of the sample remains as comparison sample and start value.

[0110] Example 1.1: 0.5 % Ester and sunflower oil

[0111] The following samples are tested and an effect of an ester can be observed on the oxidation of sunflower oil.

[0112] Table 2: Results of the Oxipres testing containing 0.5 wt.-% ester and sunflower oil.

[0113] Sample IP PF

[0114] [h]

[0115] Sunflower oil 21.5 - lsopentylundec-10-enoate 22.7 1.02

[0116] Isobutyl undec- 10-enoate 22.8 1.03

[0117] 2-ethylhexyl undec-10-enoate 22.1 1.04

[0118] Sec-butyl undec-10-enoate 22.0 1.04

[0119] Heptyl Undecylenate 21.9 1.03

[0120]

[0121] Neopentyl Diheptanoate & Isododecane 21.9 1.03

[0122] Example 1.2: Sunflower oil and 0.5 wt.-% ester boosted with 0.1 wt.-% tocopherol

[0123] Samples were prepared comprising 0.5 wt.-% sunflower oil as well as 0.1 wt.-% tocopherol. It can be observed that the effect of tocopherol (an antioxidant) on the composition is higher, when also an ester as silicone replacer is present. Alpha tocopherol as well as natural tocopherol was used.Table 3: Results of the Oxipres testing containing 0.5 wt.-% ester, sunflower oil and 0.1 wt.-% tocopherol.

[0124] Alpha Natural Tocopherol Tocopherol Sample IP [h] PF IP [h] PF Sunflower oil without Tocopherol 21.5 - 21.5 - (Placebo)

[0125] Sunflower oil with Tocopherol 29.0 1.35 37.1 1.73 lsopentylundec-10-enoate 30.2 1.40 39.5 1.84 Isobutyl undec- 10-enoate 30.9 1.44 38.8 1.80 2-ethylhexyl undec-10-enoate 30.5 1.42 39.3 1.83 Sec-butyl undec-10-enoate 30.2 1.40 39.3 1.83 Heptyl Undecylenate 30.4 1.41 38.6 1.80

[0126]

[0127] Neopentyl Diheptanoate & Isododecane 30.4 1.41 38.1 1.77

[0128] Example 1.3: Sunflower oil and 0.5 wt.-% ester boosted with 0.1 wt.-% tocopherolacetate

[0129] Samples were prepared comprising 0.5 wt.-% sunflower oil as well as 0.1 wt.-% tocopherolacetate. It can be observed that the effect of tocopherolacetate (an antioxidant) on the composition is higher, when also an ester as silicone replacer is present.

[0130] Table 4: Results of the Oxipres testing containing 0.5 wt.-% ester, sunflower oil and 0.1 wt.-% tocopherolacetate.

[0131] Tocopherolacetate

[0132] Sample IP [h] PF

[0133] Sunflower oil without tocopherolacetate 21.5 - (Placebo)

[0134] Sunflower oil with Tocopherolacetate 28.5 1.33 lsopentylundec-10-enoate 30.0 1.40 Isobutyl undec- 10-enoate 30.0 1.40 2-ethylhexyl undec-10-enoate 31.0 1.44 Heptyl Undecylenate 30.0 1.40

[0135]

[0136] The data show that the effect of an ester of formula (I) can further be boosted with an antioxidant.

Claims

Claims1. Cosmetic composition comprisingi) at least one ester of formula In(i)wherein n is selected from 3 to 12, andwherein R is selected from C3 to C12 saturated and unsaturated alkylgroups, which are branched in alpha-, beta- and / or gamma-position in relation to oxygen and wherein each branch is individually selected from methyl, ethyl or propyl,wherein the ester of formula I is not olfactorily active, andii) at least one natural oil component.

2. Cosmetic composition according to claim 1 , wherein the at least one natural oil component is selected from the group consisting of caprylic / capric triglyceride, Argania Spinose kernel oil, Cannabis Sativa seed oil, Ricinus Communis (castor) seed oil, Crambe Abyssinica seed oil, Abies Alba Seed Oil, Acacia Victoriae Seed Oil, Actinidia Chinensis (Kiwi) Seed Oil, Amaranthus Hypochondriacus Seed Oil, Simmondsia Chinensis (Jojoba) Seed Oil, Arachis Hypogaea (Peanut) Oil, Astrocaryum Murumuru Seed Butter, Astrocaryum Tucuma Seed Butter, Astrocaryum Tucuma Seed Oil, Astrocaryum Vulgare Fruit Oil, Astrocaryum Vulgare Kernel Oil, Avena Sativa (Oat) Kernel Oil, Brassica Alba Seed Oil, Brassica Campestris (Rapeseed) Seed Oil, Butyrospermum Parkii (Shea) Oil, Butyrospermum Parkii (Shea) butter, Calendula Officinalis Seed Oil, Calophyllum Inophyllum Seed Oil,Calophyllum Tacamahaca Seed Oil, Camellia Oleifera Seed Oil, Camellia Reticulata Seed Oil, Camellia Sinensis Seed Oil, Cannabis Sativa Seed / Stem Oil, Canola Oil, Carthamus Tinctorius (Safflower) Seed Oil, Chlorella Vulgaris Oil, Citrullus Lanatus (Watermelon) Seed Oil, Citrus Aurantifolia (Lime) Seed Oil, Citrus Aurantium Dulcis (Orange) Seed Oil, Citrus Grandis (Grapefruit) Seed Oil, Cocos Nucifera (Coconut) Oil, Cocos Nucifera (Coconut) Seed Butter, Coffea Arabica (Coffee) Seed Oil, Chlorella Oil (biotech), Corylus Americana (Hazelnut) Seed Oil, Corylus Avellana (Hazelnut) Seed Oil, Cucumis Melo (Melon) Seed Oil, Cucumis Sativus (Cucumber) Seed Oil, Cucurbita Pepo (Pumpkin) Seed Oil, Elaeis Guineensis (Palm) Oil, Elaeis (Palm) Fruit Oil, Glycine Soja (Soybean) Oil, Gossypium Herbaceum (Cotton) Seed Oil, Gossypium Hirsutum (Cotton) Seed Oil, Helianthus Annuus (Sunflower) Seed Oil, Macadamia Integrifolia Seed Oil, Macadamia Ternifolia Seed Oil, Mangifera Indica (Mango) Seed Butter, Mangifera Indica (Mango) Seed Oil, Melissa Officinalis Seed Oil, Microalgae Oil, Moringa Oleifera Seed Oil, Moringa Peregrina Seed Oil, Oenothera Biennis (Evening Primrose) Oil, Olea Europaea (Olive) Fruit Oil, Olus Oil, Orbignya Oleifera Seed Oil, Orbignya Speciosa Kernel Oil, Oryza Sativa (Rice) Bran / Germ Oil, Oryza Sativa (Rice) Bran Oil, Oryza Sativa (Rice) Germ Oil, Oryza Sativa (Rice) Lipids, Oryza Sativa (Rice) Seed Oil, Papaver Somniferum Seed Oil, Passiflora Edulis Seed Oil, Persea Gratissima (Avocado) Butter, Persea Gratissima (Avocado) Oil, Prunus Amygdalus Dulcis (Sweet Almond) Oil, Prunus Armeniaca (Apricot) Kernel Oil, Prunus Persica (Peach) Kernel Oil, Punica Granatum Seed Oil, Pyrus Malus (Apple) Seed Oil, Ricinoleic / Caproic / Caprylic / Capric Triglyceride(s), Rosa Canina Fruit Oil, Rosa Moschata Seed Oil, Rubus Idaeus (Raspberry) Seed Oil, Sesamum Indicum (Sesame) Seed Butter, Soybean Glycerides, Theobroma Cacao (Cocoa) Seed Butter, Theobroma Grandiflorum Seed Butter, Triticum Vulgare (Wheat) Bran Lipids, Triticum Vulgare (Wheat) Germ Oil, Vitis Vinifera (Grape) Seed Oil, Zea Mays (Corn) Germ Oil, and Zea Mays (Corn) Oil.

3. Cosmetic composition according to claim 1 or 2, wherein the composition further comprises at least one antioxidant, preferably selected from the group consisting of vitamin E, ferulic acid, coenzyme Q10, resveratrol, green tea extract, niacinamide, glutathione, alpha-lipoicacid, polyphenols, astaxanthin, beta-carotene, rosemary extract, panthenol, dimethylmethoxy chromanol, 4- hydroxyacetophenone, ascorbic acid and its salts, hydroxymethoxyphenyldecanone, beta-aspartyl arginine, uric acid, urea, hydroxypinacolone retinoate, vitamin A and vitamin A derivatives, butylhydroxytoluol (BHT), butylhydroxyanisol (BHA), hydroxyphenyl propam idobenzoic acid, ascorbyl palmitate, ascorbyl phosphate and salts thereof, carnosine, rutin, tocopherol, tocopheryl acetate, ubiquinone-10, dilauryl thiodipropionate, pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, triethyl citrate, diethylhexyl syringylidenemalonate, lactobacillus ferment, lactobacillus filtrate, lactobacillus lysate, cannabinoids, cannabidiol and its extracts, cannabinol, hydroxyphenyl propam idobenzoic acid, Zingiber Officinalis root extract, tropolone, allantoin, o-cymen-5-ol, phenylethyl resorcinol, sodium metabisulfite, mixtures of two or more of said antioxidants.

4. Cosmetic composition according to any one of the preceding claims, wherein the composition comprises at least one additional cosmetic component different from (ii), selected from the group consisting of antimicrobials, viscosity controlling agents and 1,2-alkandiols.

5. Cosmetic composition according to any one of the preceding claims, wherein R is selected from a C3 to C8 alkyl group, which is branched and wherein each branch is individually selected from methyl or ethyl.

6. Cosmetic composition according to claim 5, wherein the branched alkyl group is branched in alpha, beta and / or gamma position in relation to oxygen.

7. Cosmetic composition according to any one of the preceding claims, wherein the at least one ester of formula I is an ester of formula IIo(II)8. Cosmetic composition according to any one of the preceding claims, wherein the ratio between the at least one ester of formula I or formula II and the at least one natural oil component is 1 : 100 to 1 : 1 , preferably 1 :50 to 1 :2.

9. Cosmetic composition according to any one of the preceding claims, wherein at least one antioxidant is present and the ratio between the at least one ester of formula I or formula II to antioxidant is 20:1 to 2.5:1, preferably 10:1 to 5:1.

10. Preparation, preferably a cosmetic preparation, comprising the cosmetic composition according to any one of claims 1 to 9, preferably in an amount of from 0.001 to 99.5 wt.-%, preferably of from 0.01 to 50 wt.-%, especially preferable of from 0.05 to 20 wt.-% and moreover especially preferable of between 0.1 to 10 wt.-% depending on the total weight of the composition.

11. Preparation according to claim 10, wherein the preparation is selected from leave-on or rinse-off personal care products, preferably selected from the group consisting of shampoos, cleansing products, preferably shower gels, body washes and soaps, wet wipes, leave-on and rinse-off conditioners, hair butters and waxes, beard care and hair oils.

12. Use of at least one ester of formula (I)o. / JI Rn ociwherein n is selected from 3 to 12, andwherein R is selected from C2 to C12 saturated and unsaturated alkylgroups, which are optionally branched in alpha-, beta- and / or gamma-position in relation to oxygen and wherein each branch is individually selected from methyl, ethyl or propyl,for conveying an antioxidant effect to a natural oil component and / or boosting the antioxidative effect of at least one antioxidant in a cosmetic composition or cosmetic preparation.

13. Use according to claim 12, wherein the at least one ester is selected from the group consisting of 2-methylbutyl dodec-11 -enoate, isopentyl undec-10- enoate (3-methylbutyl dodec-11 -enoate), 2-methylbutyl undec-10-enoate, isobutyl undec-10-enoate, 2-ethylhexyl undec-10-enoate, sec-butyl undec- 10-enoate (1 -methylpropyl dodec-11 -enoate), isopentyl undec-10-enoate (3- methylbutyl undec-10-enoate) octan-3-yl undec-10-enoate, isopentyl dec-9- enoate, 2-methylbutyl dec-9-enoate, isobutyl dec-9-enoate, 2-ethylhexyl dec-9-enoate, sec-butyl dec-9-enoate, octan-3-yl dec-9-enoate, isopentyl oct-7-enoate, 2-methylbutyl oct-7-enoate, isobutyl oct-7-enoate, 2-ethylhexyl oct-7-enoate, sec-butyl oct-7-enoate, octan-3-yl oct-7-enoate, isobutyl undec-10-enoate (2-methylpropyl undec-10-enoate), isopentyl dec-9-enoate (3-methylbutyl dec-9-enoate), sec-butyl dec-9-enoate (1 -methylpropyl dec-9- enoate), isopentyl hept-6-enoate (3-methylbutyl hept-6-enoate), 2- methylbutyl hept-6-enoate, isobutyl hept-6-enoate (2-methylpropyl hept-6- enoate) 2-ethylhexyl hept-6-enoate, octan-3-yl hept-6-enoate or a mixture thereofor wherein the ester is an ester of formula II.

14. Use according to claim 12 or 13, wherein the ratio between the at least one ester of formula I or formula II and the at least one natural oil component is 1:100 to 1:1, preferably 1:50 to 1:2.

15. Use according to any one of claims 12 to 14, wherein at least one antioxidant is present in the cosmetic composition or preparation and the ratio between the at least one ester of formula I or formula II to antioxidant is 20:1 to 2.5:1, preferably 10:1 to 5:1.

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