New cosmetic compounds as silicone replacers

Abstract

The present invention lies in the field of cosmetics and provides novel cosmetic compositions comprising compounds that can serve as silicone replacers in cosmetic applications. Furthermore, uses of the disclosed silicone replacers are provided.

Description

[0001] Eisenfuhr Speiser

[0002] Munich, 18 September 2025

[0003] Our Ref.: SM 6974-02WO SOE / DRE / tko

[0004] Applicant: Symrise AG

[0005] Serial Number: Subsequent Application

[0006] Symrise AG

[0007] MuhlenfeldstraBe 1 , 37603 Holzminden, Germany

[0008] New cosmetic compounds as silicone replacers

[0009] The present invention lies in the field of cosmetics and provides novel compounds that can serve as silicone replacers in cosmetic applications. Furthermore, cosmetic compositions as well as uses of the disclosed silicone replacers 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 skin0 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 thicken5 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. In moisturizers, 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 a focus on a more sustainable industry, it is desired to have compounds with the same benefits and conditions as currently available silicones, but that can be produced from a natural source. Currently used silicone substances are inorganic synthetic polymers and are not biodegradable.

[0013] 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. The objective technical problem as disclosed in this European patent was to provide esters providing a light skinfeel when incorporated as an emollient into personal care formulations, which meet a “natural” standard.

[0014] 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 “Bio-based 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". However, the need for new substances that can serve as silicone replacers is continuously high. It was thus the primary object of the present invention to provide new compounds having desired properties for the use in cosmetic compositions.

[0015] The primary object of this invention was solved by providing a cosmetic composition comprising a compound of formula (I), wherein n is selected from 3 to 12, preferably 3 to 11 , and, wherein R is selected from a C3 to C8 branched alkyl group, and wherein each branch individually is selected from methyl or ethyl.

[0016] Further objects underlying the present invention follow from the description below and the present patent claims.

[0017] Surprisingly, it was found in terms of the present invention that compounds as defined herein and comprised in cosmetic compositions according to the invention exhibit the same desired properties as petrochemically derived silicones, such as dimethicone, dimethiconol, amodimenthicone, and cyclopentasiloxane. Thus, the compounds according to the invention can serve as replacers for petrochemically silica-derived silicones in cosmetic compositions. Furthermore, it was observed that the compounds of the present invention could also exhibit superior cosmetic properties in comparing to petrochemically silica-derived silicones.

[0018] A “replacer” in terms of the present invention means a compound having the same or similar properties in comparison to another substance, which should not be used due to toxicological, environmental, or health concerns. In terms of the present invention, the inventive compounds described herein should replace cosmetic compounds known in the art as “silicones”, as these substances are not biodegradable and derived from petrochemical origins.

[0019] Preferably, the cosmetic composition according to the invention comprises a mixture of a compound of formula (I) and an isomer thereof. Especially preferably, the ratio between compounds of formula (I) and isomers is from 99.9 : 0.1 to 0.1 to 99.9. preferably from 75:25 to 25:75 and especially preferably 70:30.

[0020] In the context of the present invention, it is preferred that an isomer is to be understood as one of several species that have the same atomic composition but different line formulae or different stereochemical formulae and hence different physical and / or chemical properties. Preferably, an isomer is to be understood as structural (or constitutional) isomer. Constitution describes the identity and connectivity (and corresponding bond multiplicities) of the atoms in a molecular entity (omitting any distinction arising from their spatial arrangement). This means that a structural isomer of a compound is a compound that contains the same number and type of atoms, but with different connectivity between them.

[0021] The compound as defined herein comprised in cosmetic compositions 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 a natural origin and not petrochemically derived.

[0022] Suitable starting materials may be 10-undecylenic acid preferably obtained from castor oil, Isoamyl alcohol and / or 2-ethylhexanol preferably obtained by fermentation of sugar cane, Isobutanol preferably obtained from biotechnological processes or 9-decenoic acid preferably obtained by ethenolysis of oleic acid.

[0023] 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. 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.

[0024] Preferably in the method according to the invention, at least 25 %, preferably at least 30 %, further preferably at least 35 %, particularly preferably at least 40 %, further particularly preferably at least 45 %, more preferably at least 50 %, even further preferably at least 55 %, especially preferably at least 60 %, even more preferably at least 65 %, particularly more preferably at least 75 %, further preferably at least 80 %, even further preferably at least 85 %, particularly preferably at least 90 %, even further preferably at least 95 %, more preferably at least 97.5 %, even more preferably all of the carbon of the compound(s) as defined herein and comprised in a cosmetic composition is non-petrochemically-derived, based on the total carbon content of the compound(s) as defined herein and comprised in a cosmetic composition.

[0025] Methods for determining whether and which proportion of the carbon of a compound is petrochemically-derived and / or non-petrochemically-derived are known to a skilled person. In the context of the present invention, radiocarbon dating, e.g. according to the ASTM D6866-16 method (https: / / www.astm.org / d6866-16.html), is preferably used. The method is described as a standard method for determining the biobased content of solid, liquid, and gaseous samples and 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.

[0026] Preferably, the compounds as defined herein comprised in cosmetic compositions according to the present invention have 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 total carbon of the respective compound is non-petrochemically derived carbon, based on the total carbon content of the respective compound as determined by radiocarbon dating.

[0027] It was further found that the components according to formula (I) are biodegradable, which thus renders them suitable for being used as silicone replacers, e.g. as defined herein.

[0028] Preferably, the branched alkyl group is branched in alpha, beta and / or gamma position in relation to oxygen.

[0029] Preferably, the branched alkyl group is branched in beta and / or gamma-position in relation to oxygen.

[0030] 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.

[0031] Preferably, the residue R of formula I is selected from a C4 to C8 branched alkyl group. A C4 to C8 alkyl group in terms of the present invention means an alkyl group having the corresponding number of carbon atoms. In particular a C4 to C8 alkyl group is a butyl, pentyl, hexyl, heptyl or octyl group and a “branched” alkyl group is one of the aforementioned having alkyl branches at one or more carbon atoms.

[0032] Preferably n is selected from a number, preferably an even number, from 4 to 12, preferably from 4 to 10, further preferably from 6 to 10. Especially preferably, n is 7. Especially preferably, n is 8. Especially preferably, n is 10. Especially preferably, n is 11.

[0033] Furthermore, n is preferably in a range of from 7 to 12, more preferably in a range of from 8 to 11. According to a preferred embodiment of the present invention the compound(s) of formula (I) is / are selected from the group consisting of

[0034] Isopentyl dodec- 11 -enoate (3-methylbutyl dodec- 11 -enoate),

[0035] 2-methylbutyl dodec-11 -enoate, isobutyl dodec- 11 -enoate (2-methylpropyl dodec-11 -enoate), 2-ethylhexyl dodec-11 -enoate, sec-butyl dodec- 11 -enoate (1 -methylpropyl dodec- 11 -enoate), isopentyl undec- 10-enoate (3-methylbutyl undec-10-enoate),

[0036] 2-methylbutyl undec-10-enoate, isobutyl undec-10-enoate (2-methylpropyl undec-10-enoate),

[0037] 2-ethylhexyl undec-10-enoate, sec-butyl undec-10-enoate (1 -methylpropyl undec-10-enoate), isopentyl dec-9-enoate (3-methylbutyl dec-9-enoate),

[0038] 2-methylbutyl dec-9-enoate, isobutyl dec-9-enoate (2-methylpropyl dec-9-enoate),

[0039] 2-ethylhexyl dec-9-enoate, sec-butyl dec-9-enoate (1 -methylpropyl dec-9-enoate), octan-3-yl dec-9-enoate, isopentyl hept-6-enoate (3-methylbutyl hept-6-enoate),

[0040] 2-methylbutyl hept-6-enoate, isobutyl hept-6-enoate (2-methylpropyl hept-6-enoate),

[0041] 2-ethylhexyl hept-6-enoate, sec-butyl hept-6-enoate (1 -methylpropyl hept-6-enoate), octan-3-yl hept-6-enoate, preferably selected from the group consisting of isopentyl undec- 10-enoate (3-methylbutyl undec-10-enoate),

[0042] 2-methylbutyl undec-10-enoate, isobutyl undec-10-enoate (2-methylpropyl undec-10-enoate),

[0043] 2-ethylhexyl undec-10-enoate, sec-butyl undec-10-enoate (1 -methylpropyl undec- 10-enoate), isopentyl dec-9-enoate (3-methylbutyl dec-9-enoate).

[0044] According to another preferred embodiment of the present invention, the compound(s) of formula I is / are not selected from the group consisting of esters of 7-octenoic acid (particularly 2-methylpropyl esters of 7-octenoic acid), esters of 5- hexenoic acid (particularly 2-methylpropyl esters of 5-hexenoic acid), and isobutyl- 9-decenoate.

[0045] Preferably, the term “2-methylpropyl esters of 7-octenoic acid” refers to or includes the compound CH2=CH(CH2)5COOCH2CH(CH3)2. Preferably, the term “2-methylpropyl esters of 5-hexenoic acid” refers to or includes the compound CH2=CH(CH2)3COOCH2CH(CH3)2.

[0046] According to another preferred embodiment of the present invention, the compound of formula I is not isopentyl undecenoate. According to another preferred embodiment of the present invention, the compound(s) of formula I is / are not selected from the group consisting of esters of 7-octenoic acid (particularly 2-methylpropyl esters of 7-octenoic acid), esters of 5- hexenoic acid (particularly 2-methylpropyl esters of 5-hexenoic acid), and isobutyl- 9-decenoate and isopentyl undecenoate. Especially preferably, the cosmetic compound according to formula I is a compound of formula II

[0047] 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.

[0048] Also, the present invention preferably relates to cosmetic compositions comprising at least one compound of formula (II) as well as at least one compound of formula (HI)

[0049] (III).

[0050] Preferably, the cosmetic composition according to the present invention is a dermatological, skin care, or hair care product.

[0051] Also preferably, the cosmetic composition comprises a mixture of compounds of formula (I) and isomers thereof as described herein. Also preferably, the cosmetic composition comprises a mixture of compounds of formula (II) and (III) as described herein.

[0052] Preferably, the cosmetic composition comprises the compound according to the present invention in an amount of from 0.001 to 100 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.

[0053] In case, the cosmetic composition comprises the compound according to the present invention in an amount of 100 wt.-%, no other components are present and the compound according to the invention is the cosmetic composition.

[0054] Preferably the composition comprises at least one further substance selected from the group consisting of skin and hair care conditioning agents, skin and hair care softening agents, and skin and hair care repairing agents; 1 .2-alkandiols, preferably selected from the group consisting of 1 ,2-pentanediol,

[0055] 1.2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2- decanediol or mixtures thereof, preferably wherein the at least one 1 ,2-alkanediol is 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol or 1 ,2-octanediol; preservatives, preferably selected from the group consisting of acidic preservatives, parabens, or phenylhydroxyalkyl ethers; specifically other cosmetically active substances, preferably selected from the group consisting of abrasives, anti-acne agents and sebum reduction agents, antiaging agents, antibacterial agents, anti-cellulite agents, anti-inflammatory agents, irritation-preventing agents, anti-irritants (anti-inflammatory, irritation-inhibiting and irritation-preventing agents), antioxidants, astringents, antiseptic agents, antistatic agents, binders, buffers, carriers, chelating agents, cell stimulants, cleansing agents, surface-active substances, deodorants and antiperspirants, emulsifiers, enzymes, essential oils, fibers, film formers, fixers, foaming agents, foam stabilizers, antifoaming agents, foam boosters, fungicides, gelling agents and gelforming, 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, UV absorbing agents and UV filters, 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.

[0056] Preferably, the at least one additional compound is comprised in an amount of from 0.001 to 80 wt.-%, preferably of from 0.002 to 50 wt.-%, particular preferably 0.05 to 30 wt.-% dependent on the total weight of the cosmetic composition.

[0057] It is preferred that the cosmetic composition according to the invention is of natural origin. Preferably, the composition is selected from the group consisting of emulsions, 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.

[0058] Moreover preferably, the composition is selected from the group consisting of leave-on or rinse-off personal care products, preferably selected from the group consisting of shampoos, cleansing products, and hair conditioning products, preferably shower gels, body washes and soaps, wet wipes, leave-on and rinse- off conditioners, hair masks, hair butters and waxes, beard care products, and hair serums and oils.

[0059] Another aspect of the present invention relates to the use of a compound as defined herein as silicone replacer in cosmetic compositions. Especially preferably, the compound is an ester of formula II.

[0060] Silicones typically lead to a dry, soft, and silky feel of the hair (mainly when the hair is dry), light film formation, smoothness, light to medium combability, and good detangling effect. The film formed by silicone is partially occlusive and provides a smooth, light, dry, velvety, and non-sticky after-feeling.

[0061] Preferably, the term “silicone replacer” refers to or includes substance(s), which have a similar physicochemical and sensory performance as silicones. Preferably, one, two, three or more, or all sensory attributes of dry hair selected from softness, ease of combing, shine, volume and frizz control, and alignment are similar to or better than that provided by a silicone compound, preferably amodimethicone, preferably cyclopentasiloxane, preferably dimethicone, preferably dimethiconol. Preferably, the physicochemical and sensory performance can be measured by sensory assessments made by a trained panel and / or by instrumental test e.g. luster and combability.

[0062] Preferably, the term “similar”, as used herein, describes an evaluation by a panel (preferably trained panel), wherein the evaluation of the silicone compound and the silicone replacer does not diverge by more than 50 %, preferably not more than 40 %, further preferably not more than 30 %, particularly preferably not more than 20 %, especially preferably not more than 10 %, based on the evaluation of the silicone compound.

[0063] Preferably, the term “better”, as used herein, describes an evaluation by a panel (preferably trained panel), wherein the evaluation of the silicone replacer is at least 10 %, preferably at least 15 %, further preferably at least 20 %, higher, based on the evaluation of the silicone compound and for positive (e.g. desired) parameters. Preferably, the difference is statistically significant, with a p-value of p < 0.05.

[0064] Additionally or alternatively, preferably, the term “better”, as used herein, describes an evaluation by a panel (preferably trained panel), wherein the evaluation of the silicone replacer is at least 10 %, preferably at least 15 %, further preferably at least 20 %, lower, based on the evaluation of the silicone compound and for negative (e.g. undesired) parameters. Preferably, the difference is statistically significant, with a p-value of p < 0.05.

[0065] Preferably, in terms of the use according to the invention, the cosmetic composition is 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.

[0066] Preferably, in terms of the use according to the invention, the composition is selected from the group consisting of emulsions, 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.

[0067] In the following, the invention is further characterized using exemplary, non-limiting examples. 1. Instrumental test

[0068] Within the scope of the examples, the compound 1 having the following structural formula (II) was tested. The Greek letters a, and y represent the branching positions in relation to oxygen.

[0069] Formula (II)

[0070] The easiness of comb bleached hair when wet and dry was evaluated using the MTT175 from Dia-Stron. Five hair tresses (3 g and 25 cm long) were evaluated per treatment. A standard shampoo formulation was applied to each tress followed by the application of a rinse-off conditioner containing or not 2% of tested compounds. Five measurements were performed for each hair tress. The average energy necessary to comb the tresses (total work) was calculated and the results of the ester or silicone containing treatment groups were compared to that of placebo- treated one. P-values below 0.05 on Student’s T test were considered significant.

[0071] The results are shown below in table 1. The parameter “combability” means the ease of combing.

[0072] Table 1 : Results of combability test

[0073] Improvement versus placebo (%)

[0074] „ Combability Wet Combability Dry amp es (Conditioner @2%) (Conditioner @2%)

[0075] Compound 1 18* 15*

[0076] CYCLOPENTASILOXANE -9 -19*

[0077] P=<0.05 2. Sensory test

[0078] Textured hair tresses (curl type IV- 3 g and 17 cm long) were treated with standard shampoo formulation and a rinse-off conditioner containing or not 2% of tested compounds. Sensory attributes of dry hair such as softness, ease of combing, shine, volume and frizz control, and alignment were evaluated by a trained panel (n=15). Scores from 0 (worst possible) to 10 (best possible) were given for each attribute using a 10 cm linear scale. The average score for each attribute was calculated for each treatment and compared with the placebo.

[0079] The results are shown in table 2.

[0080] Table 2: Results of the sensory test

[0081] Sensory test: Improvement versus placebo (%);

[0082] Samples .. Ease of . . Volume Frizz . .. .

[0083] Softness . . Shine _ . . . Alignment

[0084] (Conditioner @2%) combing Control Control

[0085] Compound 1 25* 20* 3 61* 48* 42*

[0086] AMODI METH ICON E 5 10 -5 38* -4 5

[0087] CYCLOPENTASILOXANE 5 -6 -8 45* 25* 24*

[0088] DIMETHICONE &

[0089] DIMETHICONOL z -a -a a r z

[0090] *P<0.05

[0091] 3. Formulation examples

[0092] 3.1 Rinse-off conditioner

[0093] Ingredient Concentration

[0094] (INCI name) (w / w%)

[0095] Aqua q.s. 100

[0096] Disodium EDTA 0.05

[0097] Phenoxyethanol, Hydroxyacetophenone, Caprylyl Glycol, 1.00

[0098] Water (Aqua)

[0099] Behentrimonium Chloride 1.00

[0100] Compound of formula I, e.g. Compound 1 2.00

[0101] Cetearyl Alcohol 4.50

[0102] Ceteareth-20 0.80

[0103] Stearamidopropyl Dimethylamine 0.50

[0104] Capryl ic / Capric triglyceride 3.50

[0105] Citric Acid q.s. pH 3.5-4.5

[0106] 3.2 Pearlized shampoo Ingredient Concentration

[0107] (INCI name) (w / w%)

[0108] Aqua q.s. 100

[0109] Disodium EDTA 0.10

[0110] Sodium Laureth Sulfate 25.00

[0111] Acrylates Copolymer 6.50

[0112] Sodium Hydroxide q.s. pH 6.8-7.0

[0113] Cocoamidopropyl Betaine 7.00

[0114] Compound of formula I, e.g. Compound 1 1.00

[0115] Phenoxyethanol, Hydroxyacetophenone, Caprylyl Glycol, 1.00

[0116] Water (Aqua)

[0117] Cocamide MEA 3.00

[0118] Glycol Distearate (and)Sodium Laureth Sulfate (and) 3.00

[0119] Water

[0120] Citric Acid q.s. pH 5.5-6.5

[0121] 4. Test of further compounds of formula (I) 4.1 Luster Assessment

[0122] The efficacy of branched undecylenic acid ester molecules in enhancing hair luster values compared to silicones was investigated. 4.1.1 Samples

[0123] 4.1.2 Assay Principle

[0124] Luster evaluation test analyses the light reflection from the hair surface, and other interactions of the incident light with the hair, in order to quantify the visual perception of the gloss. The measurement is made using SAMBA system (Bossa Nova Vision, USA).

[0125] 4.1.3 Methodology

[0126] Five Caucasian hair tresses per group (Regular bleached - I HIP, 2.5 g and 25 cm long) were washed with SLES (sodium laureth sulfate) 10% solution and air dried at controlled conditions (22 ± 2 °C and 55 ± 5% RH). The luster of untreated hair tresses was measured using the Samba system (Bossa Nova Vision) - TO. Test products were applied to each tress (3 drops of product + massaging for spreading the product). The luster of the treated tresses was measured using Samba system (Bossa Nova Vision) - T1 ; The luster variation was calculated. Comparisons among treatments were performed using one-way variance analysis (ANOVA), followed by Tukey’s honestly significant difference (HSD) test, or Student’s T-test for means at a 95% confidence interval.

[0127] 4.1.4 Results

[0128] Luster is a parameter calculated considering the amount of reflected light, the sharpness of the reflection, and the background on which the reflection is observed. The higher the luster, the higher the visual perception of hair gloss.

[0129] As shown beneath, higher luster values were obtained after treatment for all molecules tested compared to non-treated hair. The treatment with tested esters provided more luster to the hair than that with cyclopentasiloxane.

[0130] *P<0.01 versus non-treated. 4. II Combability Assessment

[0131] The efficacy of branched undecylenic acid ester molecules in depositing on hair surface, helping lubricating the fibers, and, consequently, improving combability, was investigated.

[0132] 4.11.1 Samples

[0133] 4. II.2 Assay Principle

[0134] In the combability evaluation, the force required for a standard comb to pass through a hair tress is measured. The parameter examined is the total work, given in Joules, which represents the total energy required for the whole combing process to happen. Since the hair surface characteristics are dependent on the cuticle / comb interaction, hair in wet or dry conditions may present different values in the measurements.

[0135] 4. II.3 Methodology

[0136] Five Caucasian hair tresses per group (Strong bleached - Kerling international - 3 g and 25 cm long) were cleaned with SLES 10% solution for 1 minute. Test products were applied to each tress:

[0137] Shampoo placebo: 30 s wetting (4 L / min at 33 ± 3 °C), 0.1 g product / g hair, 1 min massaging, 1 min rinsing (4 L / min at 33 ± 3 °C); Conditioner: 0.1 g product / g hair, 1 min massaging, 1 min rinsing (4 L / min at 33 ± 3 °C);

[0138] The test in wet condition was performed using the MTT175 (Dia-Stron). Tresses were washed 3 times with SLES 10% solution and test products were reapplied as described above. Tresses were left to dry overnight at controlled conditions (22 ± 2 °C and 55 ± 5% RH). The test in dry condition was performed using the MTT175 (Dia-Stron). The energy involved in the combing process was extracted from the measurements. Comparisons among treatments were performed using Student’s T-test for means or one-way variance analysis (ANOVA), followed by Fisher’s least significant difference (LSD) test, at a 95% confidence interval.

[0139] 4. II.4 Results

[0140] The improvement % in terms of total work observed for the hair treated with the formulation containing the studied esters and silicones relative to the placebo- treated or non-treated hair is described in the tables beneath, wherein the first one describes wet conditions and the following one dry conditions.

[0141] #P<0.1 versus reference (non-treated or placebo) using Student’s T-test. In general, it is possible to affirm that all ester molecules tested presented performance equivalent to silicones in decreasing the energy necessary to comb the damaged hair in wet condition. *P<0.05 versus reference (non-treated or placebo) using Student’s T-test.

[0142] #P<0.1 versus reference (non-treated or placebo) using Student’s T-test.

[0143] When conducting the test on dry hair, the ester-containing treatments delivered even better results for hair combability improvement compared to silicones.

[0144] 4. Ill Volume / Frizz Control Assessment

[0145] The efficacy of branched undecylenic acid ester molecules in creating a hydrophobic film on hair surface and, consequently, controlling the increase in volume and frizz during the drying process, was investigated.

[0146] 4.111.1 Samples

[0147] 4.111.2 Assay Principle

[0148] Volume increase is the gain of body in a hair tress due to moisture content variations or mechanical actions such as combing or friction of fibers. Frizz is the bristling of some fibers of hair that get apart from the tress body. Volume I Frizz control test measures the variation in the shape of the hair tresses during the drying process or after exposure to a high-humidity environment for a controlled period of time.

[0149] 4.111.3 Methodology

[0150] Five textured hair tresses per group (Curl IV - I HIP, 3 g and 17 cm long) were cleaned with SLES 10% solution for 1 minute. The test products were applied to each tress:

[0151] Shampoo: 30 s wetting (4 L / min at 33 ± 3 °C), 0.1 g product / g hair, 1 min massaging, 1 min rinsing (4 L / min at 33 ± 3 °C);

[0152] Conditioner: 0.1 g product / g hair, 1 min massaging, 1 min rinsing (4 L / min at 33 ± 3 °C);

[0153] Images were captured at Rumba System (Bossa Nova Vision) - TO -WET. Tresses were left to dry overnight at controlled conditions (22 ± 2 °C and 55 ± 5% RH). Images were captured at Rumba System (Bossa Nova Vision) - T1 - DRY. The variation in the number of pixels between TO and T1 was calculated. Comparisons among treatments were performed using Student’s T-test for means or one-way variance analysis (ANOVA), followed by Fisher’s least significant difference (LSD) test, at a 95% confidence interval.

[0154] 4. III.4 Results

[0155] The table beneath shows the volume increase after drying for the tresses treated with rinse-off conditioner formulation containing proposed ester molecules or silicones.

[0156] Results obtained for the treatments with the esters were statistically equivalent to that observed for Cyclopentasiloxane. The combination of 3-Methylbutyl undec-10- enoate + 2-Methylbutyl undec-10-enoate delivered the biggest improvement vesus placebo.

[0157] The results obtained on instrumental efficacy tests demonstrated that a variety of ester molecules can improve hair conditions as much as silicones, being suitable for acting as silicone replacers in hair care formulations.

Claims

Claims1 . Cosmetic composition comprising a compound of formula I,wherein n is selected from 3 to 12 and, wherein R is selected from a C3 to C8 branched alkyl group, and wherein each branch is individually selected from methyl or ethyl.

2. Cosmetic composition according to claim 1 , wherein the branched alkyl group is branched in alpha, beta and / or gamma position in relation to oxygen.

3. Cosmetic composition according to claim 1 or 2, wherein R is selected from a C4 to C8 branched alkyl group.

4. Cosmetic composition according to any one of the preceding claims, wherein the branched alkyl group is branched in beta and / or gamma-position in relation to oxygen.

5. Cosmetic composition according to any one of the preceding claims, wherein n is selected from 4 to 12, preferably from 4 to 10, further preferably from 6 to 10.

6. Cosmetic composition according to any one of the preceding claims, wherein the compound of formula I is a compound of formula II(II).

7. Cosmetic composition according to any one of the preceding claims, wherein at least 25 % of the carbon of the ester of formula I or formula II is non- petrochemically-derived, preferably when measured according to ASTM D6866-16.

8. Cosmetic composition according to any one of the preceding claims, wherein the compound is comprised in an amount of from 0.001 to 100 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.

9. Cosmetic composition according to any one of the preceding claims, wherein the composition comprises at least one additional compound selected from the group consisting of preservatives and other cosmetically active substances.

10. Cosmetic composition according to claim 9, wherein the at least one additional compound is comprised in an amount of from 0.001 to 80 wt.-%, preferably of from 0.002 to 60 wt.-%, particular preferably of from 0.05 to 40 wt.-% dependent on the total weight of the cosmetic composition.11 . Cosmetic composition according to any one of the preceding claims, wherein the composition is selected from the group consisting of emulsions, 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.

12. Cosmetic composition according to any one of the preceding claims, wherein the composition is selected from leave-on or rinse-off personal care products, preferably selected from the group consisting of shampoos, cleansing and conditioning products, preferably shower gels, body washes and soaps, wet wipes, leave-on and rinse-off conditioners and masks, hair butters and waxes, beard care products, and hair serums and oils.

13. Use of an ester as defined in any one of claims 1 to 12, preferably a compound of formula (II), as a silicone replacer in a cosmetic composition.

14. Use according to claim 13, wherein the cosmetic composition is selected from the group consisting of shampoos, cleansing and conditioning products, preferably shower gels, body washes and soaps, wet wipes, leave-on and rinse-off conditioners, hair butters and waxes, beard care and conditioners.

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