3-hydroxypropyl esters as solubility enhancers of lipophilic ingredients

Abstract

The present invention relates to the use of at least one of the compounds of formula (I) as a solubilizing or co-solubilizing agent for lipophilic substances in aqueous-based formulations.

Description

TECHNICAL FIELD

[0001] The present invention is directed primarily to the use of 3-hydroxypropyl esters and their use as solubilizers or co-solubilizers of lipophilic materials in water-based formulations. The present invention is one of a series of inventions by the same applicant, filed on the same date as the PCT patent application, of 3-hydroxypropyl esters and structurally related compounds, entitled "3-Hydroxypropyl esters as antioxidants and tocopherol boosters," "3-Hydroxypropyl esters as solubility enhancers of lipophilic ingredients," "3-Hydroxypropyl esters as foam and viscosity modifiers in surfactant-containing formulations," "3-Hydroxypropyl esters as emulsifiers," "3-Hydroxypropyl esters as antimicrobial agents," and "Antimicrobial synergism," the contents of which are incorporated herein by reference. BACKGROUND

[0002] Personal care formulations, including cosmetic and dermatological pharmaceutical formulations, are water-based complex mixtures that are primarily intended for topical application. The personal care formulations have many that contain materials that have significant lipophilicity. In fact, a wide variety of lipophilic materials are used in a wide range of personal care formulations to provide a variety of functions such as anti-inflammatory, anti-itch, anti-redness, anti-dandruff, antimicrobial, antiperspirant, anti-cellulite, antiviral, antioxidant, anti-wrinkle, skin lightening, skin tanning, pain relief, anti-swelling, skin barrier strengthening, antifungal, anti-sagging, deodorant, and skin soothing efficacy.

[0003] A drawback of using lipophilic functional materials is their poor water solubility. This property makes it particularly difficult to incorporate them into formulations that are primarily composed of water and are often provided as a liquid soap, shampoo, and gel base, including aqueous / alcoholic and aqueous / glycolic formulations. It is also challenging to make clear and non-hazy formulations with lipophilic materials, such as solutions for wet wipes, makeup removers, mouthwashes, aftershaves, cleaning solutions, hair rinses, hair and body sprays, facial serums, facial toners, deodorants, cleaning products such as floor cleaners, hand dishwashing detergents, liquid laundry detergents, room sprays, and the like.

[0004] To improve the solubility of lipophilic materials, solubilizers are widely used. Solubilizers are ingredients that aid in the solubilization, i.e., dissolution, of insoluble or poorly soluble ingredients into the corresponding medium. Suitable solubilizers are generally recognized when essential oils are incorporated into water-based formulations. Other materials that are typically solubilized in water-based formulations include perfume oils and preservatives with oil-soluble components, such as ethylhexylglycerin. In addition, many household formulations include solubilizers for dissolving functional lipophilic materials or perfume components.

[0005] Solubilizers are similar to emulsifiers because they possess both hydrophilic and lipophilic properties, but solubilizers tend to be completely soluble in water and only slightly soluble in oil. In practice, this means that solubilizers can suspend small amounts of oil. With a solubilizer, the dispersed phase has a particle size in the nanometer range, and because the solubilizer only solubilizes small amounts of the lipophilic active substance, the overall solution can still appear clear or slightly turbid.

[0006] Typically, essential oils, fragrance oils, or preservatives are solubilized in water (or hydrosols) along with oil-soluble components (such as benzyl alcohol) or other lipophilic active substances. The concentration of the component to be solubilized is usually between 0.01% and 5.0%.

[0007] Dispersants fall somewhere between solubilizers and emulsifiers. They can disperse very low concentrations of oils (such as vitamin E or even triglycerides) in water. However, solubilizers do not completely solubilize oils; the product is not completely transparent. Dispersants disperse oils in a translucent to milky white solution that remains stable over a reasonable period of time.

[0008] Besides appearance, such formulations also present safety and functional issues. In uniformly solubilized products, the lipophilic active ingredient is uniformly dispersed as extremely small droplets, and its concentration is exactly the same throughout the solution from the first splash to the last milliliter until the bottle is completely empty. Without the use of a solubilizer, the distribution of the lipophilic active ingredient in solution would be quite random and would vary depending on the application.

[0009] Many solubilizers are known. However, it goes without saying that there is no single solubilizer that meets all needs. Furthermore, many solubilizers have different negative side effects, such as increased foam formation. This behavior is undesirable in non-surfactant-based formulations. Typically, solubilizers are based on ethoxylated fatty alcohols, which have negative side effects on the skin because ethoxylated fatty alcohols increase skin penetration.

[0010] Furthermore, there is a general expectation to replace existing substances with "green" or bio-based alternatives. Therefore, there remains a need for additional substances that can improve the solubility of lipophilic substances in water-based formulations and thus enhance their availability in those formulations.

[0011] Furthermore, when searching for solubilizers, it is essential to consider that the substances used in regulated industries must be toxicologically acceptable, well-tolerated by the skin, and stable in the matrix forming the formulation. Additionally, it is preferable that the solubilizer is odorless or at least has a pleasant odor, is inexpensive, and readily available.

[0012] However, there is no clear dependency between the chemical structure of a substance on the one hand and its ability to improve the solubility of a substance on the other hand, which makes it difficult to find suitable substances. Furthermore, there is no predictable relationship between the solubility improvement, the toxicological acceptability, the tolerability and the stability of a substance. SUMMARY

[0013] In this context, it is an object of the present application to provide means and methods for improving the solubility of a lipophilic substance in a water-based formulation, thereby increasing its availability in said formulation. Optionally, it is a further object that said solubility should be maintained over a long period of time, preferably over the shelf life of a product, and that the (initial) turbidity should not increase, at least not significantly, over time. Yet another object is that the solubility improving means is environmentally friendly and compatible with intended uses including personal care uses. Yet another object is to overcome at least some of the above-mentioned negative aspects of commonly used solubilizers.

[0014] The above objects are achieved by the various aspects of the present application.

[0015] A first aspect of the present application relates to the use of at least one compound of formula (I) as a solubilizer or co-solubilizer for a lipophilic substance in a water-based formulation.

[0016] The compound of formula (I) as described herein is defined as follows:

[0017] (I)

[0018] wherein R is selected from the group of residues consisting of formula I-a to formula I-f:

[0019] (I-a)

[0020] (I-b)

[0021] (I-c)

[0022] (I-d),

[0023] (I-e) and

[0024] (I-f). In another aspect of the present application, a method of improving the solubility of a lipophilic substance in a water-based formulation comprises or consists of the following steps (a) to (d):

[0025] (a) providing at least one compound of formula (I) as defined herein;

[0026] (b) providing at least one lipophilic substance;

[0027] (c) providing a water-based base formulation; and

[0028] (d) adding at least one compound of step (a) to at least one lipophilic substance of step (b) and the base formulation of step (c) in an amount effective to increase the solubility of the lipophilic substance in the water-based formulation.

[0029] Preferably, the use as solubilizer or the increase of solubility relates to a reduction of the haze of the formulation.

[0030] The water-based formulation forms another aspect of the present application. The water-based formulation comprises the following components:

[0031] (i) at least one of the compounds of formula (I) as defined herein;

[0032] (ii) a lipophilic substance; and

[0033] (iii) water.

[0034] Surprisingly, it was found that the addition of an effective amount of at least one of the compounds of formula (I) acts as an effective solubilizer / auxiliary solubilizer for a lipophilic substance in a water-based formulation. It was further found that the lipophilic substance remains soluble over a long period of time and that the formulation remains clear and not hazy. Due to the better solubility of the lipophilic substance, a homogeneously solubilized formulation can be obtained, wherein the lipophilic substance is homogeneously dissolved. Thus, the concentration of the lipophilic substance remains the same until the formulation is completely used up by the user. Furthermore, the compounds of formula (I) as described herein allow for the easy production of water-based formulations. For example, it enables cold preparation, i.e. no heating is required during preparation, and no countermeasures for avoiding precipitation during production are required.

[0035] In addition, the compounds of formula (I) are environmentally friendly and meet the requirements for integration into personal care formulations and / or household formulations including oral care. In particular, the compounds of formula (I) are toxicologically and dermatologically acceptable, tasteless and non-ethoxylated (non-skin permeable).

[0036] Formula (I) as defined above defines the following specific compounds:

[0037]

[0038] The term "lipophilic" refers to the ability of a compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipophilic. Thus, lipophilic substances tend to dissolve in other lipophilic substances, while hydrophilic substances tend to dissolve in water and other hydrophilic substances. Accordingly, a "lipophilic" substance as defined in accordance with the present application is one that is not soluble in water at room temperature (20°C) at a concentration greater than 0.01% by weight. The water solubility of a substance is the saturated mass concentration of that substance in water at ambient temperature (20°C).

[0039] The lipophilic substance is not necessarily one compound, but can also be a mixture of compounds, for example a perfume mixture. Furthermore, the lipophilic substance can be characterized by a log PO / W value range of > 0 to 25.0. Calculated from EPISuite version 4.40 (U.S. Environmental Protection Agency; calculated with KOWWIN version 1.68), the lipophilic active component preferably has a log PO / W value range of > 0 to 20.0, more preferably of > 0 to 16.0, particularly preferably of > 0 to 5.0. The higher the log PO / W value, the poorer the solubility of the lipophilic substance in water-based formulations. More preferred is a log PO / W value range of the lipophilic active component of greater than or equal to 1.0 to less than or equal to 4.0.

[0040] The log P value (or log P O / W ) is a constant defined in the following way: log P = logio(partition coefficient). The partition coefficient, P = [organic phase] / [aqueous phase], where [ ] denotes the concentration of the solute in the partitioning between the organic and aqueous phases, in the present case between 1-octanol and water. A negative value for log P means that the compound has a higher affinity for the aqueous phase (it is more hydrophilic). When log P = 0, the compound is equally partitioned between the lipid and aqueous phases. A positive value for log P indicates a higher concentration in the lipid phase (i.e. the compound is more lipophilic). log P = 1 means that there is a 10:1 partitioning in the organic:aqueous phases.

[0041] The term "at least one", as used herein, means one member of the respective group of components following that term, or a mixture of two, three, four or five or even more different components. For example, the phrase "at least one compound of formula (I)" provides for any one of the compounds as well as all possible combinations of two, three, four or five compounds of formula (I).

[0042] Using the abbreviations shown in the above table as placeholders for the respective compounds, specific combinations of two compounds include the following:

[0043] A+B, A+C, A+D, A+E, B+C, B+D, B+E, C+D, C+E and D+E.

[0044] The specific combinations of the three compounds of formula (I) include the following:

[0045] A+B+C, A+B+D, A+B+E, A+C+D, A+C+E, A+D+E, B+C+D, B+C+E, B+D+E and C+D+E.

[0046] The specific combinations of the four compounds of formula (I) include the following:

[0047] A+B+C+D, A+B+D+E, A+C+D+E and B+C+D+E.

[0048] It is assumed that, compared to the corresponding single compound of formula (I), combinations of two, three, four, or five compounds of formula (I) may even further improve the solubility of lipophilic substances.

[0049] The term "water-based formulation" refers to a formulation that is primarily composed of water. This means that water constitutes >50 wt.% of the formulation. For example, water may constitute 60 wt.%, 70 wt.%, 80 wt.%, 90 wt.%, or even greater than 90 wt.%. Preferably, the formulation is an aqueous formulation, an aqueous / alcoholic formulation, or an aqueous / diol formulation.

[0050] When this article refers to solubility, it means equilibrium (thermodynamic) solubility in water. The equilibrium solubility of a compound is defined as the maximum amount of substance that can be completely dissolved in a given amount of water (e.g., 100 mL) at a given temperature (25 °C in this case) and pressure (10¹³ mPa in this case), and is thermodynamically valid as long as a solid phase in equilibrium with the solution phase is present.

[0051] The term “the amount by which the solubility of a lipophilic substance is effectively increased in an aqueous formulation” means that, when compared with the corresponding aqueous formulation that does not contain the compound of formula (I), the solubility of the lipophilic substance in the aqueous formulation containing the compound of formula (I) is clearly increased.

[0052] The term "solubilizing agent" as used herein denotes an agent that improves the solubility of a lipophilic substance in water. A solubilizing agent can still render the solution clear or slightly hazy if the solubility limit is exceeded, as if the compound to be solubilized were completely solubilized. This happens when the compound to be solubilized is uniformly dispersed, resulting in droplet sizes in the nanometer range. In the present invention, the compound of formula (I) can increase the amount of a lipophilic substance that can be uniformly dispersed in a water-based formulation and form droplet sizes in the nanometer range, preferably in the range of 1 nm to 500 nm, more preferably in the range of 1 nm to 100 nm, most preferably in the range of 1 nm to 50 nm.

[0053] Further aspects, embodiments and effects of the present application will arise from the following description, in particular from the examples and from the appended claims, which are to be understood as generally applicable to all uses, methods and products (formulations) of the present application described herein.

[0054] In the context of the present application, the lipophilic substance can be a substance that imparts one or more benefits, functions or operations such as one or more of the following via more than one mode of action: antimicrobial, deodorant, fragrance, antioxidant, anti-inflammatory, anti-itch, redness-reducing, skin care, anti-dandruff, antiperspirant, hair growth strengthening, anti-dark spot, anti-cellulite, antiviral, anti-wrinkle, skin lightening, skin tanning, pain-relieving, anti-swelling, skin barrier strengthening, antifungal, anti-sagging, and skin-soothing efficacy.

[0055] In a preferred embodiment of the present application, the lipophilic substance is selected from the group consisting of 2-methyl-5-cyclohexylpentanol, dimethylphenylbutanol, ethylhexylglycerin, octanoyl hydroxamic acid, tocopherol, bisabalol, o-cymen-5-ol, glyceryl octanoate, retinol palmitate, retinol, farnesol, glyceryl laurate, hydroxyacetophenone, caffeine, undecylenoyl phenylalanine, phenylethyl resorcinol, hydroxymethoxyphenyl decyl ketone, ginger (zingiber officinale) root extract, myristoyl nonapeptide-3, palmitoyl tripeptide-1, palmitoyl tetrapeptide-7, palmitoyl pentapeptide-4, hydroxypinacolone retinoate, dunaliella salina extract, sclareolide, vanillyl alcohol acetate, hydroxyphenyl propamidobenzoic acid, 4-tert-butylcyclohexanol, ubiquinone-10, climbazole, aldehyde C12, lilial, dihydromyrcenol, oxacyclohexadecen-2-one, linalyl acetate, citronellyl acetate, phenylethyl methyl ether, and mixtures of two or more of the above lipophilic agents.

[0056] To further increase the solubility of lipophilic substances, the formulation as defined herein may be combined with at least one solubilizer (different from the compound of formula (I)). The solubilizers used in this invention are preferably PEG-based solubilizers or PEG-free solubilizers. More preferably, the solubilizers are selected from PEG-40 hydrogenated castor oil, polysorbate-20, polysorbate-60, polysorbate-80, PEG-8 glyceryl cocoate, PEG-7 glyceryl cocoate, decyl glucoside, cetearyl alcohol polyether-20, cetearyl glucoside, PEG-60 hydrogenated castor oil, stearyl alcohol polyether-2, stearyl alcohol polyether-20, PPG-26-butanol polyether-26, PPG-5-lauryl alcohol polyether-5, stearyl alcohol polyether-21, tridecyl alcohol polyether-9, PEG-32, glyceryl polyether-26, polyglycerol- The group consisting of 3 distearate, methyl gluceth-20, PEG-12 laurate, polyglycerol-4 caprylate, oleyl alcohol ether-20, oleyl alcohol ether-2, polyglycerol-4 decanoate, PPG-1-PEG-9 lauryl glycol ether, polyglycerol-2 decanoate, isocetyl alcohol ether-20, PPG-13-decyltetradecyl alcohol ether-24, sodium cocoyl glutamate, sucrose trilaurate, sorbitan sesquicaprate, lauroyl alanine, heptayl glucoside, capryloyl / hexanoyl methyl glucamide, polyoxyethylene sorbitan monolaurate, polyxylene lauryl ether, PEG 400 monolaurate, sodium xylenesulfonate, sodium isopropylbenzenesulfonate, and a mixture of two or more of the above solubilizers.

[0057] In a more preferred variant, the water-based formulation described herein comprises a solubilizer selected from the group consisting of PEG-40 hydrogenated castor oil, polysorbate-20, polysorbate-60, polysorbate-80, PEG-8 glyceryl cocoate, PEG-7 glyceryl cocoate, decyl glucoside, cetearyl alcohol polyether-20, cetearyl glucoside, PEG-60 hydrogenated castor oil, stearyl alcohol polyether-2, stearyl alcohol polyether-20, PPG-26-butanol polyether-26, PPG-5-lauryl alcohol polyether-5, stearyl alcohol polyether-21, tridecyl alcohol polyether-9, and mixtures of two or more of the above solubilizers. In a particularly preferred variant, the solubilizer comprises or consists of PEG-40 hydrogenated castor oil and / or tridecyl alcohol polyether-9. In another particularly preferred variant, the solubilizer comprises or consists of polyglycerol-4 octanoate.

[0058] The solubility of the lipophilic substance in the water-based formulation can be further increased by combining the compound of formula (I) and optionally a further solubilizer with at least one hydrophilic solvent. The hydrophilic solvent which can be used in the present application is preferably selected from the group consisting of glycerol, propylene glycol, butylene glycol, isopropyl alcohol, propanediol, dipropylene glycol, propylene carbonate, ethanol, hexylene glycol, glycerol carbonate, methyl propanediol, butylene carbonate, isosorbide dimethyl ether or a mixture of two or more of the above hydrophilic solvents.

[0059] Preferred formulations are aqueous, aqueous / alcoholic or aqueous / glycolic. Aqueous / alcoholic or aqueous / glycolic based formulations comprise the aliphatic alcohol or glycol in an amount of 0.1 wt% to < 50 wt% based on the total weight of the solution. The aliphatic alcohol is preferably selected from the group consisting of ethanol, isopropyl alcohol, n-propanol. The glycol is preferably selected from the group consisting of glycerol, propylene glycol, butylene glycol or dipropylene glycol. Preferably, the total water content in the final composition having such a composition can be > 60%, more preferably > 70%, even more preferably > 80% and even more preferably > 90%. Solutions for aqueous paper towels (wipes) have a high water content. Then they can contain > 95% water or even > 98% water.

[0060] It is further preferred that the formulation is transparent or translucent.

[0061] The advantages achieved by the present application can be utilized particularly well in the case of personal care formulations and household formulations. Preferred personal care formulations and household formulations are formulated as creams, skin lotions, sticks, gels, solutions, paper towels, face masks, deodorants, shampoos, hair conditioners, make-up removers, sunscreens, dishwashing detergents, all-purpose cleaners, liquid soaps, mouthwashes and mouth sprays.

[0062] For example, in an aqueous mouthwash with low alcohol / ethanol content, the compound of formula (I) ensures good solubility of the lipophilic substance. In particular, for systems which tend to recrystallize over time after solubilization, the compound of formula (I) effectively prevents the precipitation of the lipophilic substance, such as o-cymen-5-ol, and maintains solubilization.

[0063] Further reference is made to the examples section, in which specific formulation types are exemplified.

[0064] Optional ingredients of the formulations as described herein include one or more of the following: abrasives, anti-acne agents, anti-aging agents, anti-cellulite agents, antidandruff agents, anti-inflammatory agents, antimicrobial agents, irritation preventatives, irritation suppressants, antioxidants, astringents, deodorants, perspiration inhibitors, preservatives, antistatic agents, binders, buffering agents, carrier materials, chelating agents, cell stimulants, cleansing agents, depilatory agents, surface active substances, deodorants, antiperspirants, emollients, enzymes, enzyme inhibitors, essential oils, fibers, film formers, fixatives, foam formers, foam stabilizers, anti-foaming substances, foam boosters, gelling agents, gel formers, hair care agents, hair fixatives, hair straighteners, active moisturizers, humectants, moisture-retaining substances, bleaching agents, strengthening agents, soil removal agents, optical brighteners, impregnating agents, anti-stain agents, dyeing agents, friction-reducing agents, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, covering agents, polishing agents, preservatives, gloss agents, green and synthetic polymers, powders, proteins, re-oiling agents, abrasives, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin lightening agents, skin protecting agents, skin softening agents, hair growth promoters, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, surfactants, UV absorbers, UV filters, primary sunscreen factors, secondary sunscreen factors, detergents, fabric conditioners, suspending agents, skin tanning agents, active substances for regulating the pigmentation of the skin or hair, matrix metalloproteinase inhibitors, skin moisturizers, glycosaminoglycan stimulants, TRPV1 antagonists, desquamation agents, anti-cellulite agents or lipofilling agents, hair growth activators or inhibitors, thickening agents, rheological additives, vitamins, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, color-protecting agents, colors, corrosion inhibitors, fragrances or essential oils, aromas, flavoring substances, odoriferous substances, polyols, electrolytes, organic solvents, and mixtures of two or more of the aforementioned substances.

[0065] Preferred ingredients of the formulations as described herein include one or more of the following: anti-aging agents, antimicrobial agents, antioxidants, chelating agents, surfactants, preservatives, green and synthetic polymers, skin cooling agents, rheological additives, oils, fragrances, essential oils, and polyols.

[0066] Examples of the above optional and preferred ingredients as well as further ingredients which can be included in the formulations as described herein can be found in paragraphs

[0284] to

[0351] of WO 2022 / 122935.

[0067] In a preferred embodiment, the formulation comprises at least one compound of formula (I) in an amount of 0.01 wt.-% to 10 wt.-%, preferably 0.05 wt.-% to 2.5 wt.-%, more preferably 0.1 wt.-% to 1.0 wt.-%, based on the total weight of the formulation. Within this range, a solubility increase is observed, resulting in a stable formulation which remains clear and does not become turbid over a long period of time. The solubility increase can be at least 5%, at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, at least 50% or even more than 50% compared to a corresponding formulation without a compound of formula (I).

[0068] In a particular embodiment, water and at least one compound of formula (I) are comprised in the formulation in a weight ratio of 10,000:1 to 10:1, preferably 5,000:1 to 100:1, more preferably 2,000:1 to 200:1. Furthermore, at least one compound of formula (I) and at least one lipophilic substance are comprised in a weight ratio of 1:100 to 50:1, preferably 1:50 to 10:1, more preferably 1:20 to 5:1, most preferably 1:10 to 1:1.

[0069] While the foregoing description is based on compounds of formula (I), compounds of formula (I) are only to be understood as preferred compounds of the present disclosure and aspects, embodiments, features and effects described in connection with compounds of formula (I) are to be understood as corresponding applicable to compounds of the present disclosure. This means, for example, that a compound of formula (II) can be used instead of a compound of formula (I) for the purposes, methods or formulations described herein. This also means, for example, that in preferred compounds of formula (II), X is as defined in formula (I), or preferred formulations can comprise the same amount of a compound of formula (II) as described for a compound of formula (I).

[0070] Compounds of formula (II) are defined as follows:

[0071] wherein n = 1-10, preferably n = 2-10, more preferably 3-10,

[0072] wherein X is:

[0073] • a linear C5-C 14 , preferably C6-C 14 , more preferably C7-C 13 , still more preferably C8-C 12 , most preferably C9-C 11 alkyl or alkenyl group; or

[0074] • is selected from the group consisting of:

[0075] or

[0076] wherein R 3 is -OCH3, -OCH2CH3, or -O(CH2)2CH3,

[0077] wherein if n = 1 :

[0078] • R 1 is selected from the group consisting of -H and -OH, and R 2 is selected from the group consisting of -H, -CH2(OH), -CH(OH)-CH2(OH), and -CH(OH)-CH(OH)-CH2(OH); or

[0079] • R 1 is -OH, and R 2 and the -OH group shown in Formula (II) are linked together to form the following Formula (II-a) compound:

[0080] (II-a); or

[0081] • R 1 and R 2 are linked together to form the following Formula (II-b) compound:

[0082] (II-b);

[0083] wherein if n = 2-10: 1 R 2 is -OH, and R 3 = -H.

[0084] When X is R 3 (as defined above) can be on any of the free carbon atoms of the benzyl ring, i.e., X can be selected from the group consisting of:

[0085] , , , and .

[0086] Structures of particular interest are:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] The compounds of formula (I) can not only be obtained via precursors of petrochemical origin, but advantageously also in a sustainable and / or cost-effective manner from bio-based starting materials which contain only non-fossil fuel-based carbon. The assessment of bio-based carbon in a material can be performed by standard test methods. The bio-based content of a material can be determined using radiocarbon and isotope ratio mass spectrometry analysis. ASTM International, formally known as the American Society for Testing and Materials, has established a standard test method for assessing the bio-based content of materials. The ASTM method is designated ASTM D6866. According to one preferred embodiment of the present application, more than 50% of the carbon atoms contained in the compounds of formula (I) are bio-based, based on the total number of carbon atoms contained in the compounds of formula (I). More preferably, more than 60%, 70%, 75%, 80%, 85% or 90% of the carbon atoms contained in the compounds of formula (I) are bio-based, based on the total number of carbon atoms contained in the compounds of formula (I). The same applies to the compounds of formula (II).

[0097] The present application is further described with reference to the following examples, which are for illustration only and do not limit the present application. DETAILED DESCRIPTION

[0098] Example:

[0099] 1. Material

[0100] 1.1 Lipophilic ingredient

[0101] The lipophilic ingredients tested included 2-methyl 5-cyclohexylpentanol, dimethyl phenyl butanol, ethylhexylglycerin, octanoyl hydroxamic acid, perfume 1 (product code 482105) Citrus Fresh NX fragrance, perfume 2 (product code 816918) Classico Power NX fragrance. Perfume 1 and perfume 2 are complex perfume mixtures with low solubility in water.

[0102]

[0103] 1.2 3-hydroxypropyl esters

[0104] The following 3-hydroxypropyl esters have been used in the experiments:

[0105]

[0106]

[0107] Compounds of formula (I) and compounds of formula (II) can be obtained, for example, by following the synthesis methods described in: Synthesis, 2003, (15), 2373-2377; Journal of the Korean Chemical Society, 2002, 46(5); Tetrahedron Letters, 2015, 56(15), 1973-1975; and JP2011207990A.

[0108] 2. Sample preparation and evaluation

[0109] 2.1 Liquid lipophilic ingredients

[0110] The samples were prepared as follows: The lipophilic ingredient and the corresponding 3-hydroxypropyl ester were pre-mixed with the glycol and the solubilizer. Heating to 60°C was performed while stirring. Water was added and stirring was continued for 10 minutes. The turbidity was evaluated 24 hours after preparation.

[0111] The samples were analyzed via visual evaluation and characterized using the following scale.

[0112] Description Code Clear C Very slightly hazy T-- Slightly hazy T- Hazy T Highly hazy T+ Extremely highly hazy T++ Settling S

[0113] The turbidity was measured via TURB IR430 ex WTW with scattered turbidity units (NTU) in triplicate

[0114] 2.2 Octanohydroxamic acid (solid lipophilic ingredient)

[0115] The samples were prepared according to the following protocol: Octanohydroxamic acid and the corresponding 3-hydroxypropyl ester were pre-mixed with the glycol and the solubilizer. Heating to 60°C was performed while stirring. Water was added and stirring was continued for 10 minutes. The crystals were filtered after 24 hours of storage at room temperature (20°C to 25°C). The filtrate and the crystals were dried for 24 hours at 40°C.

[0116] 3. Results

[0117] 3.1 2-methyl 5-cyclohexylpentanol

[0118] a) in combination with PEG-based solubilizers:

[0119]

[0120] The turbidity (visual and measured) of the tested 3-hydroxypropyl ester was observed to be lower compared to placebo (no 3-hydroxypropyl ester). It was concluded that the solubility of 2-methyl 5-cyclohexylpentanol in aqueous solution can be improved by the addition of a hydroxypropyl ester.

[0121] b) in combination with a solubilizer that does not contain PEG:

[0122]

[0123] 3.2 Dimethylphenylbutanol

[0124]

[0125] The turbidity (visual and measured) of the hydroxypropyl ester was lower compared to placebo. The solubility of dimethylphenylbutanol in aqueous solution can be improved by the ester.

[0126] 3.3 Ethylhexylglycerin

[0127]

[0128] The turbidity (visual and measured) of the hydroxypropyl ester was lower compared to placebo. The solubility of dimethylphenylbutanol in aqueous solution can be improved by the ester.

[0129] 3.4 Caprylylhydroxamic acid

[0130]

[0131] The addition of propylene glycol caprylate caused less recrystallization of caprylylhydroxamic acid compared to placebo.

[0132] 3.5 Fragrance 1 Citrus Fresh NX fragrance

[0133]

[0134] 3.6 Fragrance 2 Classico Power NX fragrance

[0135]

[0136] 4. Formulation examples

[0137]

[0138] In the following examples, the amounts of all formulations are expressed in weight %.

[0139] 4.1 Deodorant

[0140] 4.1.1 ACH-containing deodorant spray

[0141] Ingredients EU INCI Amount Triethyl citrate Triethyl citrate 3.0 Solubilizer ® ]]> PEG-40 Hydrogenated Castor Oil, Trideceth-9, Propylene Glycol, Water 1.0 3-Hydroxypropyl Benzoate 0.3 Ethanol 96% Ethanol 30.0 Ethylhexylglycerin Ethylhexylglycerin 0.3 SymDeo ® B125]]> 2-Methyl 5-Cyclohexylpentanol 0.25 SymClariol ® ]]> Decadiol 0.25 Frescolat ® ML]] Menthyl Lactate 0.6 Tego ® Cosmo P 813MB Polyglyceryl-3 Octanoate 0.5 Locron ® L (50%)]] Water, Hydroxyaluminum Chloride 25.0 Essential Oil Fragrance 0.5 Deionized Water Water 38.65

[0142] 4.1.2 Cooling and soothing deodorant upgrade

[0143] Ingredients INCI Amount Water Water To 100 Veegum ® HS granules Magnesium Aluminum Silicate 1.0 Glycerin Glycerin 5.0 EDTA Na2 Disodium Ethylenediaminetetraacetate 0.1 Dracorin ® 100 SEP]]> Glycerin Stearate, PEG-100 Stearate 6.0 Lanette 16 Cetyl Alcohol 2.0 Eumulgin ® B2]]> Ceteth-20 6.0 Eutanol ® G]] Octyldodecanol 8.0 Dow Corning FZ-3196 Volatile Octamethyl Silsesquioxane 4.0 Tween 20 Polysorbate 20 0.3 SymDeo ® B125]]> 2-Methyl 5-Cyclohexylpentanol 0.3 3-Hydroxypropyl Octanoate 0.2 Dragosantol ® 100]]> Bisabalol 0.05 Water Water 15.0 Locron ® P]]> Hydroxyaluminum Chloride 15.0 SymOcide ® PS]]> Phenoxyethanol, Decadiol, 1,2-Hexanediol 1.0 Frescolat ® ML]] Menthyl Lactate 0.5 Vitacel ® CS020]]> Cellulose 1.0 Extrapone ® Rose quartz GW Water, Glycerin, Xanthan Gum, Quartz Powder 1.0 Essential Oil Fragrance 1.0 Sodium Hydroxide 10% Solution Water, Sodium Hydroxide 0.5

[0144] 4.1.3 Sports fitness deodorant

[0145] Ingredients INCI Amount SymLite ® G8]] Glycerin Octanoate 0.15 Ethanol Denatured Alcohol To 100 SymClariol ® ]]> Decadiol 0.25 SymDeo ® B125]]> 2-Methyl 5-Cyclohexylpentanol 0.25 Frescolat ® ML]] Menthyl Lactate 0.5 Extrapone ® Ginseng Propylene Glycol, Water, Ginseng Root Extract, Lactic Acid 0.1 3-Hydroxypropyl 4-Methoxybenzoate 0.1 Extrapone ® Peppermint Water, Propylene Glycol, Peppermint Leaf Extract 0.1 Ethylhexylglycerin Ethylhexylglycerin 0.2 Essential Oil Fragrance 1.0

[0146] 4.1.4 Deodorant stick

[0147] Ingredients INCI Amount Sodium Stearate Sodium Stearate 8.0 PPG-3 Myristyl Ether PPG-3 Myristyl Ether 70.0 1,2-Propanediol 1,2-Propanediol 10.0 1,1-Dimethyl-3-phenylpropanol 1,1-Dimethyl-3-phenylpropanol 0.2 2-Butyloctanoic Acid 2-Butyloctanoic Acid 0.2 Essential Oil Fragrance 0.6 Water Water To 100 SymDeo ® Upgrade Lauryl Alcohol, Phenoxyethanol, 2-Benzyloctanol, Decadiol 0.5 3-Hydroxypropyl Dodecanoate 0.4 N-Ethyl-p-menthane-3-carboxamide (Coolant WS-3) Ethyl Menthane Carboxamide 0.3

[0148] 4.1.5 Antiperspirant stick

[0149] Ingredients INCI Amount PCL-Liquid ® 100 Cetethyhexanoate To 100 Silicone Oil 345 Cyclopolydimethylsiloxane 10.0 Crodacol™ C90 Cetyl Alcohol 8.0 Syncrowax™ HGLC C18-36 Triglyceride 8.0 Crodamol™ PTC Pentaerythrityl Tetraoctanoate / Decanoate 5.0 Syncrowax™ HRC Triarachidin 4.0 Brij™ O5 Oleyl Alcohol Polysiloxane-5 1.0 Titanium Dioxide Titanium Dioxide 1.0 Frescolat ® ML Nat Menthyl Lactate 0.75 Rezal 36GP Tetrachlorohydroxyaluminum GLY 20.0 Dry-Flo ® C]]> Aluminum Starch Octenylsuccinate 22.5 N-Ethyl-p-menthane-3-carboxamide (Coolant WS-3) Ethyl Menthane Carboxamide 0.5 Frescolat ® MGA]]> Menthone Glyceryl Acetal 0.6 Preservative Phenoxyethanol 0.8 3-Hydroxypropyl Decanoate 0.7 Essential Oil Fragrance 0.6

[0150] 4.1.6 Deodorant formulation in the form of a roll-on gel

[0151] Ingredients INCI Amount 1,3-Butylene Glycol 1,3-Butylene Glycol 2.0 3-Hydroxypropyl Dodecanoate 0.3 Cremophor ® CO 40 Surfactant PEG-40-Hydrogenated Castor Oil 2.0 Hydroxyethylcellulose Hydroxyethylcellulose 0.5 Essential Oil Fragrance 0.3 1,3-Propanediol 1,3-Propanediol 0.5 SymGuard® CD 3-Phenylpropanol, o-Cymen-3-ol, Decadiol 0.4 Ethylhexylglycerin Ethylhexylglycerin 0.1 3-hydroxypropyl 4-methoxybenzoate 0.2 Water q.s. 100

[0152] 4.1.7 Pure deodorant antiperspirant roll-on

[0153] Ingredient INCI Amount Methocel™ E4M Premium Hydroxypropyl Methylcellulose 0.5 Water Water q.s. 100 Neo-PCL Water-soluble N Trideceth-9, PEG-5 Ethylhexanoate, Water 1.0 Solubilizer PEG-40 Hydrogenated Castor Oil, Trideceth-9, Propylene Glycol, Water 3.0 Deolite Dimethylphenylpropanol, Pentylene Glycol 0.5 Locron® LW Chlorohydrate 25.0 Concentrated Aloe Vera Gel 10 / 1 Aloe Barbadensis Leaf Juice 1.0 1,2-Propanediol 99 P GC Propylene Glycol 4.0 Ethanol 96% Denatured Alcohol 30.0 3-hydroxypropyl decanoate 0.9 Essential Oil Fragrance 1.0

[0154] 4.2 Gels

[0155] 4.2.1 After-shave lotion

[0156] Ingredient INCI Amount SymSol® PF-3 Water, Pentylene Glycol, Sodium Lauryl Sulfoacetate, Sodium Oleoyl 3.0 SymSitive® 1609 Pentylene Glycol, 4-tert-Butylcyclohexanol 1.0 Frescolat® ML Menthyl Lactate 0.3 Glycerin 99,5 P. Glycerin 5.0 Water Water q.s. 100 Extrapone® Glacier Water GW Glycerin, Water 1.0 SymCalmin® Butylene Glycol, Pentylene Glycol, Hydroxyphenyl Propamidine Benzoate 0.5 Dragosine® Carnosine 0.1 Hydrolite® 5 Green Pentylene Glycol 5.0 Ethanol 96% Denatured Alcohol 5.0 Color Pigment Color Pigment 0.05 Essential Oil Fragrance 0.15 3-hydroxypropyl dodecanoate 0.05 Alpha Tocopherol DL Tocopherol 0.2

[0157] 4.2.2 Cool and hot firming gel with Thermolat and Frescolat

[0158] Ingredient EU INCI Amount Water Water q.s. 100 Actipone® Orange Flower Water, Propylene Glycol, Bitter Orange Flower Extract 0.5 Cosmedia® SP Sodium Polyacrylate 1.2 PCL-Solid Stearyl Heptanoate, Stearyl Octanoate 3.5 Isodragol Triisononyl Phenol Ether 5.0 Caprylic / Capric Triglyceride Caprylic / Capric Triglyceride 1.5 Jojoba Oil Jojoba Seed Oil 1.5 SymFit® 1617 Trimethylcyclohexyl Butyl Carbamate 0.2 Tocopheryl Acetate Tocopheryl Acetate 0.3 Thermolat® Vanillyl Butyl Ether, 1,2-Hexanediol, Caprylyl Glycol 1.0 Frescolat® X-Cool Menthyl Acetamido Hexanoate 2.0 SymOcide® PS Phenoxyethanol, Decylene Glycol, 1,2-Hexanediol 1.0 Essential Oil Fragrance 0.5 3-hydroxypropyl octanoate 0.1 Citric Acid 30% Sol Gel Water, Citric Acid 0.15

[0159] 4.2.3 Creamy face foam

[0160] Ingredient EU INCI Amount Water Water q.s. 100 Edeta B Powder Tetrasodium Ethylenediaminetetraacetate 0.1 Glycerin Glycerin 3.0 Potassium Hydroxide, 85% Pellets Potassium Hydroxide 3.5 Myristic Acid 99% Myristic Acid 6.0 Laurylic Acid, 99% Laurylic Acid 6.0 Stearic Acid, 98% Stearic Acid 11.0 Miranol® C2M CONC NP Disodium Cocoampho-Diacetate 4.0 SymMollient® W / S Trideceth-9, PEG-5 Isononanoate, Water 2.0 Essential Oil Fragrance 0.3 Frescolat® MGA Upgraded Menthone Glyceryl Acetal, Menthol 0.5 SymOcide® OS Phenoxyethanol, Decylene Glycol, 1,2-Hexanediol 0.8 3-hydroxypropyl decanoate 0.6 Colorant, 0.1% Aqueous Solution CI42090 0.5

[0161] 4.2.4 Clear moisturizing face gel

[0162] Ingredient EU INCI Amount Water Water q.s. 100 Gamma-Max Sodium Polyglutamate 0.1 Glycerin 99.5% Glycerin 3.0 Genu® Gum Gellan Gum 1.0 SymOcide® OS Phenoxyethanol, Decylene glycol, 1,2 Hexanediol 0.6 SymHair ® Force 1631 Pentylene glycol, Isochrysis galbana extract 2.5 3-Hydroxypropyl dodecanoate 0.6 SymHair® Shape and Color Cetearyl isononanoate, Wheat germ oil, Caprylic / capric triglyceride, Linoleic acid, Wheat bran extract, Wheat germ extract, Camellia sinensis seed oil 0.5

[0163] 4.2.5 Intimate sensitive gel

[0164] Ingredient EU INCI Amount Water Water q.s. 100 Sodium benzoate Sodium benzoate 0.3 Keltrol® CG-T Xanthan gum 0.2 Guar gum Guar gum 0.1 Glycerin Glycerin 4.0 Tego® Betaine F50 Cocamidopropyl betaine 14.0 Solubilizer PEG-40 Hydrogenated castor oil, Trideceth-9, Propylene glycol, Water 3.0 Hydrolite® 6 1,2 Hexanediol 1.0 SymGuard® CD Phenylpropanol, o-Cymen-5-ol, Decylene glycol 0.3 SymRelief® 100 Bisabalol, Zingiber officinale root extract 0.1 Essential oil Fragrance 0.2 3-Hydroxypropyl dodecanoate 0.7 Frescolat® X-cool Menthyl acetamido oxalic acid salt 0.4 Plantacare® 2000 UP Decyl glucoside 2.0 Lactic acid 90% natural Lactic acid, Water 0.3

[0165] 4.2.6 Mild feminine wash

[0166] Ingredient EU INCI Amount Water Water 73.15 SymSave® H Hydroxyacetophenone 0.5 Keltrol® CG-T Xanthan gum 0.5 Glycerin Glycerin 2.0 Propylene glycol Propylene glycol 3.0 3-Hydroxypropyl decanoate 1.0 Tego® Betaine F50 Cocamidopropyl betaine 14.0 SymGuard® CD Phenylpropanol, o-Cymen-5-ol, Decylene glycol 0.3 Plantacare 2000 UP Decyl glucoside 2.0 Extrapone® Witch Hazel GW Glycerin, Water, Hamamelis virginiana bark / leaf / twig extract 1.0 Solubilizer PEG-40 Hydrogenated castor oil, Trideceth-9, Propylene glycol, Water 1.5 Essential oil Fragrance 0.2 SymCalmin® Pentylene glycol, Butylene glycol, Hydroxyphenyl propamidobenzoic acid 1.0 Lactic acid 90% natural Lactic acid, Water 0.32

[0167] 4.2.7 Bioacne Control Gel

[0168] Ingredient INCI Amount Distilled water Water q.s. 100 SymSave® H Hydroxyacetophenone 0.5 Carbopol® Ultrez 21 Polymer Acrylates / C10-30 alkyl acrylate crosspolymer 0.5 Solubilizer PEG-40 Hydrogenated castor oil, Trideceth-9, Propylene glycol, Water 2.5 SymClariol® Decylene glycol 0.5 SymMollient® W / S Trideceth-9, PEG-5 isononyl ester, Water 1.0 3-Hydroxypropyl benzoate 0.7 Hydrolite®-5 Green Pentylene glycol 5.0 Dragosantol® Bisabalol 0.05 Farnesol Farnesol 0.3 Ethanol Alcohol, Water 5.0 Flowerpone® Lavender PEG-40 Hydrogenated castor oil, Trideceth-9, Pentylene glycol, Lavandula angustifolia flower extract, Propylene glycol, Bisabalol 0.5 SymRebootTM L19 Maltodextrin, Lactobacillus fermentum 0.5 Sodium hydroxide 10% solution Water, Sodium hydroxide 1.1 Colorant Colorant 0.2 Essential oil Fragrance 0.3

[0169] 4.2.8 Anti-Wrinkle Gel

[0170] Ingredient INCI Amount EMT-10 Hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer 1.2 CC Dicaprylyl carbonate 2.0 SpecKareTM 3GF Glycerin, linoleic acid, glycerin, oleic acid, glycerin, linolenic acid 1.0 EH Ethylhexylglycerin 2.0 CDM3526 C26-28 alkyl dimethicone 0.2 SpecKareTM VEA Tocopheryl acetate 0.2 Glycerin Glycerin 8.0 SpecThem® XTG200 Xanthan gum 0.18 SpecThem® SCB21 Acrylates / C10-30 alkyl acrylate crosspolymer 0.15 SpecKareTM ALLA Allantoin 0.1 H-200 Glycerin polyacrylate 6.0 Distilled water Water To 100 SpecPure® PC1 (1% liquid) Poria cocos sclerotium extract 2.0 SpecKareTM HAL (1% liquid) Sodium hyaluronate 5.0 EDTA-2Na Disodium EDTA 0.1 SpecKareTM NMF50 Betaine 2.0 Triethanolamine Triethanolamine 0.13 NK2 Dipotassium glycyrrhizate 0.1 ParbFree® PCG Caprylyl glycol, phenoxyethanol 0.8 3-hydroxypropyl 4-methoxybenzoate 0.6 Essential oil Fragrance 0.1 SpecPed® Co-De BPS Polyglyceryl-10 triisostearate, caprylic / capric triglyceride, butylene glycol, glycerin, hexylene glycol, myo-inositol, lecithin, hydroxylated lecithin, cholesterol, palmitoyl tripeptide-5, acetyl tetrapeptide-5, palmitoyl pentapeptide-4, water 5.0

[0171] 4.2.9 Cleansing Micellar Gel

[0172] Ingredient INCI Amount Distilled water Water To 100 Carbopol® ETD 2050 polymer Carbomer 0.7 Hydroviton® Upgraded 2290 Water, pentylene glycol, glycerin fructose, urea, citric acid, sodium hydroxide, maltose pca sodium, sodium chloride lactic acid sodium, trehalose allantoin, sodium hyaluronate glucose 2.0 SymOcide® PS Phenoxyethanol, decylene glycol, 1,2-hexanediol 1.0 Sodium hydroxide 10% solution Water, sodium hydroxide 3.28 SymMollient® W / S Trideceth-9, PEG-5 isononanoate, water 1.0 SymSol® PF-3 Water, pentylene glycol, sodium lauryl sulfoacetate, sodium oleoyl methyl taurate, sodium chloride, sodium oleate 3.0 Essential oil Fragrance 1.0 3-hydroxypropyl octanoate Propylene glycol octanoate 0.4 SymVital® AR Zingiber officinale (ginger) root extract 0.2 Extrapone® Algae Water glycol chondrus extract 1.0 Actipone® Taraxacum officinale (dandelion) juice (organic) GW Glycerin taraxacum officinale juice 1.0 Colorant I Colorant 0.35 Colorant II Colorant 0.20 Capryloyl hydroxamic acid Capryloyl hydroxamic acid 0.2 Phenylpropanol Phenylpropanol 0.2

[0173] 4.2.10 Sprayable Anti-cellulite Gel

[0174] Ingredient INCI Amount Water Water To 100 Stabileze QM PVM / Ma decadiene crosspolymer 0.25 Sodium hydroxide 10% solution Water, sodium hydroxide 0.4 Pure caffeine Caffeine 0.5 Extrapone® Horse chestnut Propylene glycol, water, aesculus hippocastanum (horse chestnut) seed extract, glucose, lactic acid 1.0 Hydrolite® 5 Pentylene glycol 3.0 1,3 Butylene glycol Butylene glycol 5.0 Biotive® Escin sesquihydrate Escin 0.3 Preservative Phenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben 0.8 Ethanol 96% Denatured alcohol 10.0 Solubilizer PEG-40 hydrogenated castor oil, trideceth-9, water 0.5 Essential oil Fragrance 0.2 3-hydroxypropyl decanoate 0.2 Benzyl salicylate Benzyl salicylate 0.1 Chlorphenesin Chlorphenesin 0.1

[0175] 4.3 Wipes

[0176] 4.3.1 PEG-Free Wet Wipes

[0177] Ingredient INCI Amount Tegosoft® PC 41 Polyglyceryl-4 caprate 2.0 Tegosoft® M Isopropyl myristate 0.2 3-Hydroxypropyl benzoate 0.5 Essential oil Fragrance 0.1 Propylene glycol Propylene glycol 3.0 Distilled water Water To 100 Cetrimonium bromide, 40% Cetrimonium bromide 0.25 Hydroxyethoxyphenyl butanol Hydroxyethoxyphenyl butanol 0.6

[0178] 4.3.2 Intimate Wipes

[0179] Ingredient INCI Amount Dracorin® GO C Glycerol oleate citrate, caprylic / capric triglyceride 2.2 PCL-Liquid® 100 Cetyl stearyl alcohol ethylhexanoate 3.0 SymCalmin® Pentylene glycol, butylene glycol, hydroxyphenyl propamidobenzoic acid 1.0 Frescolat® X-Cool Menthyl acetylamino oxalate 0.5 3-Hydroxypropyl benzoate 1.0 Essential oil Fragrance 0.2 Distilled water Water To 100 Pemulen™ TR-2 polymer emulsifier Acrylates / C10-30 alkyl acrylate crosspolymer 0.2 SymOcide® PH Phenoxyethanol, hydroxyacetophenone, caprylyl glycol, water 1.3 Potassium sorbate Potassium sorbate 0.1 Extrapone® Chamomile GW Glycerin, water, German chamomile, Matricaria flower extract 0.5 Sodium hydroxide 10% solution Water, sodium hydroxide 0.45 PCA ethyl cocoamino acid PCA ethyl cocoamino acid 0.1

[0180] 4.4 Oral Care

[0181] 4.4.1 Protective Mouthwash

[0182] Ingredient EU INCI Amount Cremophor CO 40 surfactant PEG-40 hydrogenated castor oil 3.0 Flavor Fragrance 0.5 SymGuard® CD Phenylpropanol, o-cymen-5-ol, decylene glycol 0.3 Glycerin Glycerin 5.0 Propylene glycol Propylene glycol 10.0 3-Hydroxypropyl octanoate Propylene glycol octanoate 0.3 SymOcide® PH Phenoxyethanol, hydroxyacetophenone, caprylyl glycol, water 0.5 Sorbitol liquid EP 70% Sorbitol 10.0 Water Water To 100 Saccharin sodium Saccharin sodium 0.1 Colorant I 1.2 Colorant II 0.2

[0183] 4.4.2 Alcohol-Free Mouthwash (Ready-To-Use)

[0184] Ingredient EU INCI Amount Cremophor® CO 40 PEG_40 hydrogenated castor oil 2.5 SymGuard® CD Phenylpropanol, o-cymen-5-ol, decylene glycol 0.5 Propylene glycol Propylene glycol 5.0 3-Hydroxypropyl decanoate 0.4 Flavor Fragrance 0.2 Water Water To 100 Sorbitol liquid EP 70% Sorbitol 10.0 Saccharin sodium Saccharin sodium 0.07 Sodium fluoride Sodium fluoride 0.18 SymSave® H Hydroxyacetophenone 0.3

[0185] 4.4.3 Concentrated Mouthwash

[0186] Ingredient EU INCI Amount Ethanol Ethanol To 100 Flavor Fragrance 0.8 Menthol Menthol 0.1 Cremophor CO 40 surfactant PEG-40 hydrogenated castor oil 3.0 3-Hydroxypropyl 4-methoxybenzoate 0.4 Disodium azacycloheptane diphosphate Disodium azacycloheptane diphosphate 0.5 Cetypyridinium chloride Cetypyridinium chloride 0.1 Zinc chloride Zinc chloride 0.1 Disodium phosphate Disodium phosphate 0.15 Trisodium phosphate Trisodium phosphate 0.05 Sodium fluoride Sodium fluoride 0.18 Water Water 45

[0187] 4.4.4 Breath-Freshening Mouth Spray

[0188] Raw material INCI Amount Water Water To 100 Sorbitol liquid EP 70% Sorbitol 10.0 Saccharin sodium Saccharin sodium 0.1 Cremophor® CO 455 PEG-40 hydrogenated castor oil, propylene glycol 5.0 3-Hydroxypropyl dodecanoate 0.3 Flavor Fragrance 0.8 Frescolat® ML Crystals Menthyl lactate 2.0 Propylene glycol Propylene glycol 10.0 SymOcide® C O-cymen-5-ol 0.1 SymSave® H Hydroxyacetophenone 0.25 SymDiol® 68 1,2-Hexanediol caprylyl glycol 0.5 Extrapone® Peppermint Water, propylene glycol, peppermint leaf extract 2.0 Colorant 0.194

[0189] 4.5 Facial Masks

[0190] 4.5.1 Sheet Mask - New Skin

[0191] Ingredient EU INCI Amount EDTA NA2 Disodium EDTA 0.1 Water Water q.s. 100 SymSave® H Hydroxyacetophenone 0.5 Glycerin Glycerin 5.0 Sepimax™ ZEN Polyacrylate Crosspolymer-6 0.4 Hydrolite® 5 Green Pentylene glycol 3.0 Dragosine® Carnosine 0.2 SymGlucan® Water, glycerin, 1,2-hexanediol, caprylyl glycol, beta-glucan 4.0 3-Hydroxypropyl decaonate 0.5 Extrapone® Glacier Water GW Glycerin, water 1.0 Essential oil Fragrance 0.15 Tocopherol Tocopherol 0.1 Dragosantol® 100 Bisabalol 0.05 Solubilizer PEG-40 Hydrogenated Castor Oil, Trideceth-9, Water 1.0 Citric Acid 50% Sol Water, citric acid 0.12

[0192] 4.5.2 Sheet masks - super sensitive

[0193] Raw material INCI Amount Water Water q.s. 100 SymSave® H Hydroxyacetophenone 0.5 EDTA NA2 Disodium EDTA 0.1 Glycerin Glycerin 6.0 Hydrolite® 5 Green Pentylene glycol 3.0 Sepimax™ ZEN Polyacrylate Crosspolymer-6 0.5 Jojoba Oil Jojoba Seed Oil 4.0 Caprylic / Capric Triglyceride Caprylic / Capric Triglyceride 8.0 Dracorin® GOC Glycerin Oleate Citrate, Caprylic / Capric Triglyceride 2.0 Frescolat® ML Crystals Menthyl Lactate 0.2 N-Ethyl-p-menthane-3-carboxamide (Coolant WS-3) Ethyl menthane camphoramide 0.6 SymDecanox™ HA Caprylic / Capric Triglyceride, Hydroxymethoxyphenyl Decylone 1.0 3-Hydroxypropyl Octanoate Propylene Glycol Octanoate 0.8 SymSitive® 1609 Pentylene glycol, 4-tert-butylcyclohexanol 1.2 Simulgel NS Hydroxyethyl Acrylate / Sodium Acryloyldimethyl Taurate Copolymer, Squalane, Polysorbate 60 0.7 SymCalmin® Green Pentylene glycol, butylene glycol, hydroxyphenyl propamidine benzoate 2.0 SymRelief® 100 Bisabalol, Ginger Root Extract 0.05 Extraone® Watermin P Water, propylene glycol, dextrose, water peppermint leaf extract 1.0 Essential oil Fragrance 0.15 Colorant 0.4

[0194] 4.5.3 Watermelon mask and scrub

[0195] Raw material INCI Amount Water Water q.s. 100 SymSave® H Hydroxyacetophenone 0.5 Hydroviton® Upgraded 2290 Water, pentylene glycol, glycerin, fructose, urea, citric acid, sodium hydroxide, maltose, sodium PCA, sodium chloride, sodium lactate, trehalose, allantoin, sodium hyaluronate, glucose 2.0 Edeta BD Disodium EDTA 0.1 Extrapone® Watermelon GW Water, glycerin, watermelon juice 1.0 Colorant 0.3 SymSol® PF-3 Water, pentylene glycol, sodium lauryl sulfoacetate, sodium oleoyl methyl taurate, sodium chloride, sodium oleate 3.0 SymRelief 100 Bisabalol, Ginger Root Extract 0.1 3-Hydroxypropyl Benzoate 0.6 Essential oil Fragrance 0.2 Frescolt® Upgraded Menthol, Menthyl Lactate 0.2 Hydrolite® 5 Green Pentylene glycol 3.0 Aqua Keep 10SH-NFC Sodium Acrylates Crosspolymer-2 1.5 Keltrol® CG-T Xanthan gum 0.3 Tinogard Q Tris(tetramethylhydroxy piperidinol) citrate 0.05 Kiwi Exfoliator 2000 Actinidia chinensis (Kiwi) Seed 1.0

[0196] 4.6 Home care

[0197] 4.6.1 Shiny containing floor cleaner

[0198] Ingredients w / w % Water q.s. 100 Polyethylene / Sytrene-Acrylates Copolymer 2.5 PE Wax 1.5 Tributoxy Phosphine Oxide 1.5 C10-18 Ethoxylated Alcohol 1.5 PE-Wax / Orange Wax 0.2 PPG-2 Methyl Ether 2.5 Tributyl Phosphate 0.1 Methylisothiazolinone / MIT 0.005 Benzisothiazolinone / BIT 0.005 Denatonium Benzoate 0.005

[0199] 4.6.2 Easy floor cleaner

[0200] Ingredients w / w % Water q.s. 100 C13-15 Paraffinum Alcohol Polgyoxylate-3 4.0 Phenoxyethanol 0.5 Fragrance 0.2 Styrene Acrylates Copolymer 5 Ethoxydiglycol 5 Tributoxy Phosphine Oxide 0.5 Modified Polypropylene Wax 0.5 Trideceth-5 0.5 Sodium 1,4-Diisotridecylsulfobenzoate 0.5 Denatured Alcohol 0.5 MEA / Monoethanolamine / Ethanolamine 0.2

Claims

1. Use of at least one of the compounds of formula (I) as a solubilizer or co-solidator for lipophilic substances in water-based formulations. （I） R is selected from the following groups: (I-a) (I-b) (I-c) (I-d)、 (Ie) Sum (I-f)。 2. A method for improving the solubility of lipophilic substances in water-based formulations, the method comprising or consisting of the following: (a) Providing at least one of the compounds of formula (I) as defined in claim 1; (b) Provide at least one lipophilic substance; (c) Providing water-based matrix formulations; and (d) Adding the at least one compound of (a) to the at least one lipophilic substance of (b) and the matrix formulation of (c) in an amount that effectively increases the solubility of the lipophilic substance in the water-based formulation.

3. A water-based preparation comprising: (i) at least one of the compounds of formula (I) as defined in claim 1; (ii) lipophilic substances; and (iii) Water.

4. The formulation according to claim 3, wherein the lipophilic substance is selected from 2-methyl-5-cyclohexylpentanol, dimethylphenylbutanol, ethylhexylglycerin, capryloyl hydroxamic acid, tocopherol, bisabolol, o-cymene-5-ol, glyceryl caprylate, retinyl palmitate, retinol, farnesol, glyceryl laurate, hydroxyacetophenone, caffeine, undecenoyl phenylalanine, phenylethyl resorcinol, hydroxymethoxyphenyldecone, ginger (ginger) root extract, and nutmeg. The group consisting of myristoyl nonapeptide-3, palmitoyl tripeptide-1, palmitoyl tetrapeptide-7, palmitoyl pentapeptide-4, hydroxypinazone retinate, *Isophyllaria globulus* extract, sage lactone, vanillyl butyl ether, hydroxyphenyl propionamide benzoic acid, 4-tert-butylcyclohexanol, ubiquinone-10, clomiphene, aldehyde C12, lily aldehyde, dihydromyrcenol, oxetane-2-one, linaloyl acetate, citronellol acetate, phenethyl methyl ether, and mixtures of two or more of the above-mentioned lipophilic reagents.

5. The formulation according to claim 3 or 4 further comprises a PEG-based solubilizer or a PEG-free solubilizer.

6. The formulation according to claim 5, wherein the PEG-based solubilizer or the PEG-free solubilizer is selected from PEG-40 hydrogenated castor oil, polysorbate-20, polysorbate-60, polysorbate-80, PEG-8 glyceryl cocoate, PEG-7 glyceryl cocoate, decyl glucoside, cetearyl alcohol polyether-20, cetearyl glucoside, PEG-60 hydrogenated castor oil, stearyl alcohol polyether-2, stearyl alcohol polyether-20, PPG-26-butanol polyether-26, PPG-5-lauryl alcohol polyether-5, stearyl alcohol polyether-21, tridecyl alcohol polyether-9, PEG-3 2. The group consisting of glycerol polyether-26, polyglycerol-3 distearate, methyl glucetol polyether-20, PEG-12 laurate, polyglycerol-4 caprylate, oleyl alcohol polyether-20, oleyl alcohol polyether-2, polyglycerol-4 decanoate, PPG-1-PEG-9 lauryl glycol ether, polyglycerol-2 decanoate, isocetyl alcohol polyether-20, PPG-13-decyltetradecyl alcohol polyether-24, sodium cocoyl glutamate, sucrose trilaurate, sorbitan sesquicaprylate, lauroyl alanine, heptayl glucoside, capryloyl / hexanoyl methyl glucamide, polyoxyethylene sorbitan monolaurate, polyxylene lauryl ether, PEG 400 monolaurate, sodium xylenesulfonate, sodium isopropylbenzenesulfonate, and a mixture of two or more of the above solubilizers.

7. The formulation according to claim 6, wherein the PEG-based solubilizer comprises or is composed of the following: PEG-40 hydrogenated castor oil and / or tridecyl alcohol polyether-9.

8. The formulation according to claim 6, wherein the PEG-free solubilizer contains or consists of polyglycerol-4 octanoate.

9. The formulation according to any one of claims 3 to 8 further comprises a hydrophilic solvent.

10. The formulation according to claim 9, wherein the hydrophilic solvent is selected from the group consisting of glycerol, propylene glycol, butylene glycol, isopropanol, propylene glycol, dipropylene glycol, propylene carbonate, ethanol, hexanediol, glyceryl carbonate, methyl propylene glycol, butene carbonate, isosorbide dimethyl ether, or a mixture of two or more of the above hydrophilic solvents.

11. The formulation according to any one of claims 3 to 10, wherein the formulation is one or more of the following: Primarily composed of water, preferably the formulation is an aqueous formulation, an aqueous / alcohol formulation, or an aqueous / diol formulation. Transparent or translucent; The formulations are selected from personal care preparations and household preparations, preferably from the group consisting of creams, lotions, sticks, gels, solutions, tissues, face masks, deodorants, shampoos, conditioners, sunscreens, makeup removers, dishwashing liquids, multi-purpose cleaners, liquid soaps, mouthwashes, and oral sprays.

12. The formulation according to any one of claims 3 to 11, comprising, based on the total weight of the formulation, 0.01 wt.-% to 10 wt.-%, preferably 0.05 wt.-% to 2.5 wt.-%, more preferably 0.1 wt.-% to 1.0 wt.-%. of at least one compound of formula (I).

13. The formulation according to any one of claims 3 to 12, comprising the water and the at least one compound of formula (I) in a weight ratio of 10,000:1 to 10:1, preferably 5,000:1 to 100:1, more preferably 2,000:1 to 200:

1. and / or It comprises at least one compound of formula (I) and at least one lipophilic substance in a weight ratio of 1:100 to 50:1, preferably 1:50 to 10:1, more preferably 1:20 to 5:1, and most preferably 1:10 to 1:

1.

14. The use according to claim 1 or the method according to claim 2, wherein the use as a solubilizer or the increase in solubility involves reducing the turbidity of the formulation.

15. The use according to claim 1 or 14 or the method according to claim 2 or 14, wherein the formulation is defined as in any one of claims 3 to 13.

Images