Ester compound, process for preparing an ester compound, and use of the compound

Abstract

The present invention relates to a renewable-based ester compound, as well as to the process for preparing same comprising a reaction between at least one vegetable-based alcohol and at least one carboxylic acid derived from renewable sources, in the presence of conventional catalysts or biocatalysts. Furthermore, the present invention also relates to the use of the said compound in personal care and household care formulations.

Description

ESTER COMPOUND, PROCESS OF PREPARING AN ESTER COMPOUND, AND USE OF THE COMPOUND FIELD OF INVENTION

[0001] The present invention falls within the field of home care and personal care formulations. The invention suggests a plant-derived ester compound, its preparation, and use in formulations for both general personal care (makeup, deodorants, antiperspirants, conditioners, shampoos, hair or skin creams, face cleansers, sunscreens, liquid or bar soaps, shower gels, insect repellents, among other applications) and general household care (laundry detergents, fabric softeners, surface cleaners, etc.). BACKGROUND OF THE INVENTION

[0002] Waste management from industrial plants is a key issue in a wide range of production chains. Within the framework of sustainable development, reusing industrial processing byproducts to obtain other value-added products is a beneficial approach for both the environment and sustainable economic development.

[0003] Within the context of sustainable development, many efforts have also been directed towards the use of plant-based products, which are renewable sources of carbon, as an alternative to fossil-based materials.

[0004] Levulinic acid is one of the main chemical products obtained from materials of plant origin (plant biomass), which has often been suggested as a starting material for a large number of compounds, presenting diverse applications, such as in the synthesis of solvents, pesticides, polymers, polyesters, fuel additives and in the pharmaceutical industry.

[0005] Among the products derived from levulinic acid, levulinic acid esters are important platform compounds, versatile and widely applicable, presenting great importance in the industry due to their different applications as flavoring agents, lubricants, fragrances and plasticizers.

[0006] There are several documents in the state of the art that report the use of levulinic acid esters in various formulations and applications.

[0007] In this sense, document US2008720 reports the synthesis of levulinate esters through a conventional homogeneous catalysis route, where the alcohol has 7 to 18 carbon atoms. The esters thus obtained are used as plasticizers, an application outside the scope of the present invention.

[0008] In this regard, document WO2018007577 describes the use of levulinate esters as solubilizers for organic UV filters in SunCare formulations. Specifically, the fatty alcohol chain of levulinate esters has 8 to 22 carbon atoms. Examples include the use of stearyl alcohol (Cl 8) and cetearyl alcohol (a mixture of Cl 6 and Cl 8 alcohols) to prepare sunscreen formulations. These compounds generally come from non-renewable sources and can pose a number of social, economic, environmental, and ethical concerns, such as deforestation, impacts on biodiversity and local communities, land conflicts and monoculture, poor working conditions, and many other factors. However, the aforementioned document does not describe a compound obtained from 100% plant-based raw materials.

[0009] Document US9090550 describes methods for producing a variety of dehydrated sugar derivatives (levulinic acid esters) that can be used in personal care products, using microwaves as the ester production method. The method proposed in said document differs, in route and process, from the dehydrated sugar derivative, as the product can be a hydroxymethylfurfural ether when the Hexose is a glucose or can be a levulinate ester when hexose is a fructose. Furthermore, the document describes the use of microwave radiation to catalyze the reaction process.

[0010] Document US9931286 describes the use of levulinate esters in general cosmetic formulations to increase viscosity, using fatty alcohols with chains of 6 to 22 carbon atoms, preferably 8 to 18 carbon atoms, to provide a composition suitable for cosmetic applications, comprising a thickening agent based on materials of renewable origin. This document describes that fatty alcohol esters of levulinic acid are useful as thickening agents in compositions suitable for cosmetic applications. Since the fatty alcohol of the levulinic acid ester is preferably long-chain (8 to 18 carbon atoms) to act as a rheology modifier, short-chain alcohols such as isoamyl alcohol (C5) are not addressed. The document also does not describe the need for the alcohol to be of renewable origin and recycled (upcycled).

[0011] Thus, there are no reports in the prior art that anticipate an ester compound that is easy to incorporate in cold conditions and that does not freeze at low temperatures in formulations, especially those aimed at the personal and home care market, that is obtained by an esterification process using raw materials of renewable origin, especially by-products from other production processes. SUMMARY OF THE INVENTION

[0012] The present invention relates to an ester compound of renewable origin and a process for preparing the same comprising the reaction between at least one alcohol and at least one carboxylic acid of renewable origin.

[0013] The present invention also relates to the use of the compound obtained by the process according to the invention for application in formulations home care and personal care.

[0014] These objectives and other advantages of the present invention will become more evident from the description that follows. BRIEF DESCRIPTION OF THE FIGURES

[0015] Figure 1 illustrates an explanatory graph of the hydrophobicity of molecules as a function of the contact angle (4>).

[0016] Figure 2 illustrates a graph comparing the hydrophobicity of a product obtained by the process of the present invention with other compounds.

[0017] Figure 3 illustrates a graph comparing the spreadability of a product obtained by the process of the present invention with other compounds, measured by a texturometer.

[0018] Figures 4a, 4b and 4c illustrate the TGA analysis of a product obtained by the process of the present invention and comparative compounds.

[0019] Figure 5 illustrates the DSC analysis of a product obtained by the process of the present invention.

[0020] Figure 6 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of body cream samples, measured using E95 Spindle, 2 RPM.

[0021] Figure 7 illustrates a graph with the pH values ​​of body cream samples.

[0022] Figure 8 illustrates a graph with the results of spreadability tests carried out by a texturometer on body cream samples.

[0023] Figure 9 illustrates a graph with the instrumental spreadability results of samples F47 (isoamyl thalate), F48 (isoamyl levulinate) and F49 (cyclopentasiloxane - D5).

[0024] Figure 10 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of sunscreen samples, measured using E95 Spindle, 2 RPM.

[0025] Figure 11 illustrates a graph with the pH values ​​of sunscreen samples.

[0026] Figure 12 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of conditioner samples, measured using E95 Shaft, 2 RPM.

[0027] Figure 13 illustrates a graph with the pH values ​​of conditioner samples.

[0028] Figure 14 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of leave-in hair cream samples.

[0029] Figure 15 illustrates a graph with the pH values ​​of leave-in hair cream samples. DETAILED DESCRIPTION OF THE INVENTION

[0030] The ester compounds used in the state of the art related to the field of formulations for home care and personal care are generally of fossil origin and / or from sources with a high socio-environmental impact, in addition to being difficult to incorporate cold into formulations, with low application performance and which easily solidify at low temperatures.

[0031] The invention proposed herein has the potential to replace such compounds of fossil origin or that are of socially controversial origin, with materials of renewable origin, optionally originating from other production processes (reuse).

[0032] The present invention has as its first objective to provide an ester compound of formula (I): wherein Ri comprises hydrogen or about 1 to about 22 carbon atoms, the compound being saturated or unsaturated, linear or branched, more preferably from about 4 to about 18 carbon atoms, saturated or unsaturated, linear or branched, and n is a number from 0 to 5.

[0033] The compound in question is liquid or solid at room temperature, preferably liquid, which advantageously allows it to be easily incorporated into personal or household care formulations, contributing to the sustainability of the process of obtaining the formulation and its application.

[0034] In one embodiment of the present invention, the ester compound is selected from a group comprising isoamyl pyruvate, isoamyl acetoacetate, isoamyl levulinate, isoamyl 4-acetylbutyrate, isoamyl 4-acetylvalerate, or isoamyl 7-oxooctanoate. Preferably, the ester compound is isoamyl levulinate.

[0035] The second objective of the invention is to provide an esterification process that allows the aforementioned ester compound to be obtained from plant-based raw materials, which may be partially or fully renewable and may optionally originate from other production processes. Such raw materials of renewable and / or reusable origin comprise at least one alcohol and / or at least one carboxylic acid.

[0036] Preferably, the compound of the present invention is obtained from at least one alcohol having chains of about 1 to about 22 carbon atoms, preferably comprising from about 4 to about 18 carbon atoms, and may be branched or unbranched, saturated or unsaturated. Particularly, the at least one alcohol may be selected from the group consisting of 1-pentanol, 3-methyl-1-butanol, 2-methyl-1-butanol, 2,2-dimethyl-1-propanol, 3-pentanol, 2-pentanol, 3-methyl-2-butanol, 2-methyl-2-butanol, with 3-methyl-1-butanol or isoamyl alcohol being the most preferred. preferable. In addition to the isomers of isoamyl alcohol, an alcohol can also be 1-butanol, 2-butanol, tert-butanol, isobutanol, 1-hexanol, 2-hexanol, 3-hexanol, 2,3-dimethyl-2-butanol, 3,3-dimethyl-l-butanol, 2-methyl-l-pentanol, 3-methyl-l-pentanol, 4-methyl-l-pentanol, 2-methyl-2-pentanol, 3-methyl-2-pentanol, 4-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl-3-pentanol, 1-octanol, 2-octanol, 2-ethylhexanol, 1-decanol, 2-decanol, 3-decanol, 2-propylheptanol, 1- dodecanol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol, 1-eicosanol, 2-eicosanol, 3-eicosanol, their isomers, or mixtures thereof. Preferably the at least one alcohol is selected from isoamyl alcohol, its isomers or mixtures thereof.

[0037] In one embodiment of the present invention, the carboxylic acid is of renewable origin, being a carboxylic acid with chains of about 1 to about 8 carbon atoms, preferably comprising from about 3 to about 7 carbon atoms. The carboxylic acid may be saturated or unsaturated, branched or unbranched, and may even be an oxoacid. Possible examples of the carboxylic acid are selected from the group comprising pyruvic acid, acetoacetic acid, formic acid, levulinic acid, 4-acetylbutyric acid, 4-acetylvaleric acid or 7-oxooctanoic acid, their isomers or mixtures thereof. Preferably, the carboxylic acid of renewable origin comes from materials of plant origin, and may be levulinic acid (C5), its isomers or mixtures thereof, or mixtures containing levulinic acid and other compounds such as formic acid, among others. Preferably, the carboxylic acid from plant-based materials is levulinic acid (C5).

[0038] In the context of the present invention, the process of esterification of at least one alcohol and at least one carboxylic acid optionally of renewable origin comprises the steps of: i) obtaining at least one carboxylic acid optionally of renewable origin, in which the acid is branched or unbranched, saturated or unsaturated, comprising about 1 to about 8 carbon atoms; ii) obtaining at least one alcohol optionally of renewable origin, in which the alcohol is branched or unbranched, saturated or unsaturated, comprising about 1 to about 22 carbon atoms; iii) reacting the at least one alcohol obtained in step ii) with the at least one carboxylic acid of step i) in the presence of a catalyst; and iv) obtaining an ester compound of renewable origin.

[0039] Preferably, the invention provides an esterification process with reused raw materials (upcycle) from other production processes comprising at least one alcohol, optionally of vegetable origin, preferably originating from the alcoholic fermentation process, and at least one carboxylic acid originating from biomass.

[0040] The esterification process comprises the reaction between at least one carboxylic acid and at least one alcohol in molar proportions of acid of 0.5 to 1.0 mol and of alcohol of 0.8 to 1.5, preferably in the molar proportion of 1.0: 1.3 respectively.

[0041] The esterification reaction between at least one carboxylic acid and at least one alcohol occurs via homogeneous or heterogeneous, organic or inorganic catalysis, in the presence of acid catalysts, which may be conventional or biocatalysts.

[0042] The use of biocatalysts enables milder reaction conditions, making the process more economical, environmentally sustainable, and preserving the integrity of heat-sensitive compounds. When using biocatalysis, reaction temperatures typically range from about 40°C to about 80°C, with temperatures in the range of about 60°C to about 80°C being preferred, for a reaction period of about 5 to about 10 hours, with an acid:alcohol molar ratio ranging from about 1:1 to about 1:2.2, with an acid:alcohol molar ratio preferably between about 1:1 and about 1:1. of 1:1.5, also presenting the advantage of separating the biocatalyst from the reaction medium through a simple filtration step. Furthermore, there is no need for a neutralization step.

[0043] Because biocatalysts are derived from renewable sources, such as microorganisms or plants, they can be produced sustainably, reducing dependence on fossil-fuel-based raw materials. Furthermore, biocatalysts are biodegradable and do not generate toxic waste, contributing to a more environmentally friendly process.

[0044] It's also important to note that reactions involving biocatalysts typically occur in aqueous environments. For example, many enzymes are active in aqueous environments, allowing esterification reactions to be performed in non-toxic and environmentally safe solvents, reducing safety risks and minimizing environmental impact.

[0045] In the process according to the present invention, catalysts selected from the group comprising a strong Brönsted and / or Lewis acid may be used.

[0046] In particular, when biocatalysts are used, they are selected from the group comprising lipases, esterases, proteases, hydrolases, amidases, decarboxylases, dehydratases, oxidoreductases, among other enzymes or mixtures thereof.

[0047] When conventional catalysts are used, these are selected from the group comprising conventional organic or inorganic acid catalysts such as methanesulfonic acid, para-toluenesulfonic acid, xylenesulfonic acid, phosphoric acid, sulfuric acid, among others or their mixtures.

[0048] The esterification process occurs between at least one carboxylic acid and at least one vegetable alcohol at a temperature in the range of about 100°C to about 150°C, more specifically between the temperatures of approximately 105°C to approximately 115°C, in a reaction system containing a Dean-Stark apparatus for removing condensate formed during the reaction, which can occur for a period of approximately 1 to approximately 10 hours, with it being preferable to keep it between approximately 6 and approximately 8 hours.

[0049] The invention now proposed has as a third objective the use of the ester compound obtained for application in personal care and home care formulations.

[0050] More specifically, the present invention also proposes the use of said compound in personal care formulations, with the function of emollient, solubilizer of active ingredients, solubilizer of UV filters, hydrotrope, emulsifier, solvent, rheological modifier, among other functions, and can be applied in products for skin or hair in general, such as makeup, deodorants, antiperspirants, conditioners, shampoos, hair or skin creams, face cleansers, sunscreens, liquid or bar soaps, shower gel, among other applications for personal care, and in home care, and can have the function of solubilizer, hydrotrope, emulsifier, solvent, rheological modifier, among other functions, and can be applied in products such as laundry detergents, softeners, surface cleaners, among other applications.

[0051] In the context of the present invention, “low temperatures” means temperatures less than or equal to 25°C, preferably in the range between about -80°C and about 25°C.

[0052] The terms "preferred" and "preferably" refer to embodiments that may provide certain benefits in certain circumstances. However, other embodiments may also be preferred in the same or other circumstances. Furthermore, the citation of one or more preferred embodiments does not constitute a factor preventing the use of other embodiments, nor does it exclude other embodiments from the scope of the present invention.

[0053] The following description will be based on preferred embodiments of the invention. As will be evident to anyone skilled in the art, the invention is not limited to these particular embodiments. EXAMPLES Esterification process

[0054] The esterification process takes place in a reaction system consisting of a round-bottom flask with a mechanical stirrer and a Dean-Stark apparatus attached to remove condensate formed during the reaction. 116.1 g of levulinic acid is reacted with 114.6 g of isoamyl alcohol in the presence of 0.1% by mass of methanesulfonic acid as a catalyst under a N2 atmosphere at 110 °C for 7 hours. After the esterification step, the product is purified under a 100 mmHg vacuum with heating at 130 °C for 6 hours. The product is then subjected to a neutralization step initiated by a pre-wash with distilled water, followed by neutralization with sodium carbonate solution and washing with distilled water. A product drying step is performed by subjecting the reaction system to a 200 mmHg vacuum with heating at 130 °C for 6 hours. Finally, the product is vacuum filtered at room temperature.

[0055] The reaction that occurs in the esterification process is demonstrated below. Levulinic acid Isoamyl alcohol Isoamyl levulinate (Isopentanol)

[0056] The summarized steps of the process performed in the example are: reactor loading; esterification; isopentanol removal; neutralization; drying / isopentanol removal; and filtration.

[0057] Then, analyses of different Properties of the product obtained from the esterification process performed in this example. The product obtained (isoamyl levulinate) was compared with other compounds that have similar functions and can be used as emollients, namely: caprylic / capric triglyceride; coco-caprylate / caprate; cocos nucifera oil; dicaprylyl carbonate; mineral oil; isopropyl palmitate; isoamyl cocoate; isoamyl caprylate / caprate; isoamyl stearate; isoamyl thalate; decamethylcyclopentasiloxane; and dimethicone.

[0058] The first property analyzed was hydrophobicity. Figure 1 illustrates the difference between a hydrophilic molecule and a hydrophobic molecule as a function of the contact angle (([)). A hydrophilic molecule has a contact angle less than 90°; a hydrophobic molecule has a contact angle between 90° and 150°; and a superhydrophobic molecule has a contact angle greater than 150°.

[0059] Figure 2 illustrates a hydrophobicity graph of the product obtained in this example compared to other compounds that can be used as emollients. The tests were conducted based on the in vitro skin contact angle. The product obtained (isoamyl levulinate) is as hydrophilic as mineral oil and dicaprylyl carbonate, with better spreadability than mineral oil.

[0060] Next, the Hydrophilic-Lipophilic Balance (HLB) was analyzed. Application tests were performed on water-based body cream. Antifoaming agents have HLB values ​​between 1 and 3; water / oil emulsifiers have HLB values ​​between 3 and 6; wetting agents have HLB values ​​between 7 and 9; oil / water emulsifiers have HLB values ​​between 8 and 18; detergents have HLB values ​​between 13 and 15; and solubilizers have HLB values ​​between 15 and 18. The values ​​obtained are shown in Table 1 below. Table 1: HLB values ​​obtained

[0061] The above HLB measurements indicate that isoamyl levulinate can be used as an emulsifier in oil / water emulsion.

[0062] The product's spreadability was then analyzed using in-vitro skin image analysis and a texturometer, which involves using a texture analyzer (TA-XT Plus) to apply force to the cream being tested to expel it from the sample cup. The lower the force required, the greater the spreadability.

[0063] Figure 3 illustrates a graph comparing the spreadability of the product obtained with other compounds. The lower the strength, the better the spreadability; that is, isoamyl levulinate performs as well as dicaprylyl carbonate and coco-caprylate / caprate and is better than silicone.

[0064] TGA and DSC analyses were also performed on the product obtained in this example and comparative compounds to validate the thermal behavior and degradation properties when subjected to heat. Figures 4a, 4b, and 4c illustrate graphs with the results of the TGA analysis, and Figure 5 illustrates a graph with the results of the DSC analysis. The lower the degradation temperature, the more susceptible the product is to thermal degradation.

[0065] Additionally, the product obtained by this example was applied in different formulations described in this application, namely: body cream, sunscreen, conditioner, and leave-in hair cream. The formulations were tested as shown below. Body cream

[0066] Body cream samples were prepared with 5% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl levulinate). The remaining samples were prepared with 5% of comparative compounds as emollients, namely: deionized water; NaOH (50%); citric acid (50%); disodium EDTA; ceteareth-20; cetearyl alcohol; caprylic / capric triglyceride; coco-caprylate / caprate; cocos nucifera oil; dicaprylyl carbonate; mineral oil; isopropyl palmitate; isoamyl cocoate; isoamyl caprylate / caprate; isoamyl stearate; isoamyl thalate; and phenoxyethanol.

[0067] Figure 6 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of the body cream samples, measured using E95 Spindle, 2 RPM.

[0068] Sample F48 (isoamyl levulinate) exhibited low viscosity, although it is recommended as an emulsifier. The small, low-molecular-weight distribution of the molecule did not promote high viscosity and also demonstrated phase separation during stability testing. Sample FOI is a duplicate of formulation F48, a reproduction of the isoamyl levulinate synthesis incorporating process improvements to reduce the isoamyl alcohol residue and prevent phase separation. The viscosity increased, but is still lower than that of thalate and resulted in phase separation.

[0069] Figure 7 illustrates a graph of the pH values ​​of the body cream samples. The target pH is between 6.3 and 6.7.

[0070] Table 2 below presents the stability results at 5, 25 and 40°C for 90 days of the body cream samples. Table 2: Stability of body cream samples

[0071] The samples above contain the following emollients: F37 - no emollient; F38 - caprylic / capric triglyceride; F39 - coco-caprylate / caprate; F40 - cocos nucifera oil; F41 - dicaprylyl carbonate; F42 - mineral oil; F43 - isopropyl palmitate; F44 - isoamyl cocoate; F45 - isoamyl caprylate / caprate; F46 - isoamyl stearate; F47 - isoamyl thallate; F48 - isoamyl levulinate.

[0072] Figure 8 illustrates a graph with the results of the spreadability tests carried out using a texturometer on the body cream samples.

[0073] Figure 9 illustrates a graph with the results of instrumental spreadability of samples F47 (isoamyl thalate), F48 (isoamyl levulinate), and F49 (cyclopentasiloxane - D5). The lower the firmness, the easier the spreadability. Therefore, D5 showed better spreadability, and body creams formulated with isoamyl thalate and isoamyl levulinate showed similar performance. Sunscreen

[0074] Sunscreen samples were prepared with 8% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl levulinate). The remaining samples were prepared with 8% of comparative compounds as emollients, namely: deionized water; aculyn 33; NaOH (50%); citric acid (50%); disodium EDTA; octocrylene; homosalate; butyl methoxydibenzoylmethane; bis-ethylhexyloxyphenol methoxyphenyl triazine; cetearyl alcohol; potassium cetyl phosphate; C12-15 alkyl benzoate; caprylic / capric triglyceride; coco-caprylate / caprate; cocos nucifera oil; dicaprylyl carbonate; mineral oil; isoamyl thalate; isopropyl palmitate; isoamyl cocoate; isoamyl caprylate / caprate; isoamyl stearate; methylene bis-benzotriazolyl tetramethylbutylphenol; phenoxyethanol (and) caprylyl glycol; sodium hydroxide; and citric acid.

[0075] Figure 10 illustrates a graph with the values ​​obtained for the Brooksfield Viscosity (BKF) in mPa.s of the sunscreen samples, measured using E95 Spindle, 2 RPM.

[0076] Figure 11 illustrates a graph of the pH values ​​of sunscreen samples. The target pH is between 6.8 and 7.2. Hair conditioner

[0077] Hair conditioner samples were prepared with 1% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl levulinate). The remaining samples were prepared with 1% of comparative compounds as emollients, namely: deionized water; NaOH (50%); lactic acid (85%); behentrimonium chloride; disodium EDTA; ceteareth-20; cetearyl alcohol; cocos nucifera oil; dimethicone; mineral oil; isopropyl palmitate; caprylic / capric triglyceride; isoamyl cocoate; isoamyl caprylate / caprate; isoamyl stearate; dimethicone 200 / 350; isoamyl thalate; and sodium benzoate.

[0078] Figure 12 illustrates a graph with the values ​​obtained for the Brooksfield Viscosity (BKF) in mPa.s of the conditioner samples, measured using E95 Shaft, 2 RPM.

[0079] Figure 13 illustrates a graph of the pH values ​​of the conditioner samples. The target pH is between 4.3 and 4.7.

[0080] All prepared conditioner samples showed stability for 90 days at 5, 25 and 40 °C, without phase separation. Leave-in hair cream

[0081] Leave-in hair cream samples were prepared with 1% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl levulinate). The remaining samples were prepared with 1% of comparative compounds as emollients, namely: deionized water; NaOH (50%); lactic acid (85%); behentrimonium chloride; disodium EDTA; ceteareth-20; cetearyl alcohol; cocos nucifera oil; dimethicone; mineral oil; isopropyl palmitate; caprylic / capric triglyceride; isoamyl cocoate; isoamyl caprylate / caprate; isoamyl stearate; dimethicone 200 / 350; isoamyl thallate; and sodium benzoate.

[0082] Figure 14 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of the leave-in hair cream samples.

[0083] Figure 15 illustrates a graph of the pH values ​​of the leave-in hair cream samples. The target pH is between 4.3 and 4.7.

[0084] From the examples above it is possible to note that the ester compound of the present invention, liquid at room temperature, allows its cold incorporation into personal and household care formulations, in addition to having a low melting point, unlike, for example, some UV filter solubilizers currently on the market. Furthermore, because it is derived from renewable and optionally reusable raw materials, this compound proves environmentally friendly and delivers comparable, and even superior, results to those using fossil-based raw materials for the same intended purpose.

[0085] Therefore, the proposed invention advantageously provides a compound that is easily incorporated cold into personal care formulations and has a low melting point, which is typically a problem with UV filter solubilizers currently on the market. Furthermore, because it is derived from renewable and reused raw materials, the compound is environmentally friendly and has the potential to replace fossil or plant-based compounds of different origins (that are not reusable) or that are of socio-environmentally controversial origin, with materials of renewable, reusable origin.

[0086] Furthermore, the ester compound production process offers the benefit of lower carbon emissions compared to the aforementioned sources and ease of processing and incorporation into cold formulations, reducing the need for energy input from the production process to its use. Furthermore, this process facilitates waste management by reusing / recovering waste from other production processes, generating value-added products through a route that is both environmentally and economically beneficial. Its use in a variety of applications, including personal care and household care formulations, is not limited to these applications.

[0087] Such a product, process, and use have not been suggested nor are they evident from the published literature on the subject.

[0088] The description of the subject matter of the present invention should be considered only as one or more possible embodiments, and any particular features introduced therein should be understood only as something that was written to facilitate understanding. Therefore, they cannot in any way be considered as limiting the invention, which is limited to the scope of the claims that follow.

Claims

CLAIMS 1. Ester compound, characterized by being defined by the formula where Ri comprises hydrogen or about 1 to about 22 carbon atoms, the compound being saturated or unsaturated, linear or branched, and where n is a number from 0 to 5.

2. Compound, according to claim 1, characterized by the fact that the compound can be fully or partially renewable.

3. Compound according to claim 1 or 2, characterized in that it is selected from the group comprising isoamyl pyruvate, isoamyl acetoacetate, isoamyl levulinate, isoamyl 4-acetylbutyrate, isoamyl 4-acetylvalerate or isoamyl 7-oxooctanoate, preferably being isoamyl levulinate.

4. Compound according to any one of claims 1 to 3, characterized in that it is solid or liquid at room temperature, preferably liquid.

5. Compound according to any one of claims 1 to 4, characterized in that it does not freeze at temperatures less than or equal to 25°C, preferably between about -80°C and about 25°C.

6. Process for preparing an ester compound, characterized by the fact that it comprises the steps of: i) obtaining at least one carboxylic acid, in which the acid is branched or unbranched, saturated or unsaturated, comprising about 1 to about 8 carbon atoms; ii) obtaining at least one alcohol, in which the alcohol is branched or unbranched, saturated or unsaturated, comprising from about 1 to about 22 carbon atoms; iii) reacting the at least one alcohol obtained in step ii) with the at least one carboxylic acid of step i) in the presence of a catalyst; and iv) obtaining an ester compound as defined in any one of claims 1 to 5.

7. Process according to claim 6, characterized in that the at least one carboxylic acid can be saturated or unsaturated, branched or unbranched, including an oxoacid, comprising from about 3 to about 7 carbon atoms.

8. Process according to claim 6 or 7, characterized in that the carboxylic acid of renewable origin comes from materials of plant origin, and can be selected from the group comprising pyruvic acid, acetoacetic acid, formic acid, levulinic acid, 4-acetylbtyric acid, 4-acetylvaleric acid or 7-oxooctanoic acid, their isomers or mixtures thereof, preferably levulinic acid.

9. The process of claim 6, wherein the at least one alcohol is branched or unbranched, saturated or unsaturated, comprising from about 4 to about 18 carbon atoms.

10. Process according to claim 9, characterized in that the at least one alcohol is selected from the group comprising 1-pentanol, 3-methyl-1-butanol, 2-methyl-1-butanol, 2,2-dimethyl- 1-propanol, 3-pentanol, 2-pentanol, 3-methyl-2-butanol, 2-methyl-2-butanol, 3-methyl-1-butanol or isoamyl alcohol, 2-butanol, tert-butanol, isobutanol, 1-hexanol, 2-hexanol, 3-hexanol, 2,3-dimethyl-2-butanol, 3,3-dimethyl-1-butanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, 4-methyl-1-pentanol, 2-methyl-2-pentanol, 3-methyl-2-pentanol, 4-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl-3-pentanol, 1-octanol, 2-octanol, 2-ethylhexanol, 1-decanol, 2- decanol, 3-decanol, 2-propylheptanol, 1-dodecanol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol, 1-eicosanol, 2-eicosanol, 3-eicosanol, their isomers, or mixtures thereof.

11. Process according to claim 10, characterized in that the at least one alcohol is isoamyl alcohol, its isomers or mixtures thereof.

12. Process according to any one of claims 6 to 11, characterized in that the at least one alcohol and the at least one carboxylic acid are of renewable origin and reused from other production processes.

13. Process according to any one of claims 6 to 12, characterized in that the catalyst is an organic or inorganic, homogeneous or heterogeneous catalyst, or biocatalyst.

14. Process according to claim 13, characterized in that the catalyst is selected from the group comprising a strong Brönsted and / or Lewis acid.

15. Process according to claim 14, characterized in that the catalyst is selected from the group comprising methanesulfonic acid, para-toluene sulfonic acid, xylene sulfonic acid, phosphoric acid, sulfuric acid, among others or mixtures thereof.

16. Process according to claim 13 or 14, characterized in that the biocatalyst is selected from the group comprising lipases, esterases, proteases, hydrolases, amidases, decarboxylases, dehydratases, oxidoreductases, among other enzymes or mixtures thereof.

17. Process according to any one of claims 6 to 16, characterized in that step iii) occurs at a temperature ranging from about 100°C to about 150°C, preferably between about 105°C and about 115°C, in a reaction system containing a Dean-Stark apparatus. with removal of condensate formed during the reaction in a period of about 1 to about 10 hours, preferably between about 6 and about 8 hours.

18. Process according to any one of claims 6 to 17, characterized in that, when biocatalyst is used, the reaction temperatures typically vary in the range of about 40°C to about 80°C, preferably in the range between about 60°C and about 80°C, for the period of about 5 to about 10 hours of reaction, with an acid:alcohol molar ratio ranging from about 1:1 to about 1:2.2, with an acid:alcohol molar ratio between about 1:1 and about 1:1.5 being preferably used.

19. Process according to any one of claims 6 to 18, characterized in that it further comprises the steps of purifying the ester product obtained by removing excess alcohol, neutralizing and subsequently drying the final product.

20. Process according to any one of claims 6 to 19, characterized in that it comprises the reaction between at least one carboxylic acid and at least one alcohol in molar proportions of acid of about 0.5 to about 1.0 mol and of alcohol of about 0.8 to about 1.5, preferably in the molar proportion of about 1.0:1.3 respectively.

21. Use of the ester compound of renewable origin as defined in any one of claims 1 to 5, characterized by the fact that it is in cosmetic functions such as emollient, solubilizer of active ingredients, solubilizer of UV filters, hydrotope, emulsifier, solvent, rheological modifier, insect repellent, among other functions, in personal care formulations.

22. Use according to claim 21, characterized in that the personal care formulations are formulations for applications for skin or hair in general, such as makeup, deodorants, antiperspirants, conditioners, shampoo, hair or skin creams, cleansers, sunscreens, liquid or bar soaps, shower gel, among others. other applications.

23. Use of the compound as defined in any one of claims 1 to 5, characterized in that it is in domestic formulations as a solubilizer, hydrotrope, emulsifier, solvent, rheological modifier, among other functions, in domestic care formulations.

24. Use according to claim 23, characterized in that it is in household care formulations, such as laundry and general surface care products.

25. Ester compound of renewable origin, as defined in any one of claims 1 to 5, characterized in that it is obtained by means of the preparation process as defined in claim 6.

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