Ester compound, process for the preparation thereof, use of a compound, and personal or household care formulation

Abstract

The present invention relates to an ester compound of partially or fully renewable origin, as well as to a process for the preparation thereof involving the esterification of at least one vegetable alcohol with at least one fatty acid derived from the kraft process of pulping wood in the pulp and paper industry in the presence of a catalyst. Furthermore, the present invention also relates to the use of said ester compound in a personal or household care formulation, and to said personal or household care formulation.

Description

ESTER COMPOUND, PROCESS FOR PREPARING THE SAME, USE OF A COMPOUND, AND, PERSONAL OR HOUSEHOLD CARE FORMULATION FIELD OF APPLICATION

[0001] The present invention relates to an ester compound, as well as the process for preparing the same comprising the esterification between at least one alcohol and at least one fatty acid of renewable origin.

[0002] The present invention also relates to the use of the aforementioned compound for application in personal care and household care formulations in general and to a personal or household care formulation. BACKGROUND OF THE INVENTION

[0003] 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 economic development.

[0004] In the pulp and paper industry, one of the most widely used processes is the kraft process, which involves placing cellulose pulp in contact with sodium hydroxide (NaOH) and sodium sulfide (NaiS). This process produces byproducts such as carbonates, hydroxides, dregs, grits, lime sludge, and others.

[0005] Among the common byproducts of the kraft process, it is important to highlight black liquor, which, after a few steps, is characterized as Crude Tall Oil (CTO). This CTO is then distilled, producing different fractions, such as pitch, tall oil resin acids (PRES), distilled tall oil, tall oil fatty acids (TOFA), and other fractions.

[0006] TOFA is a mixture of saturated and unsaturated fatty acids and resin acids, which can vary in quantity and proportion. Typically, the alkyl chain of these fatty acids ranges from C16 to C20, and they are mostly characterized as unsaturated, linear, or branched, Cis-alkyl chains.

[0007] Still within the scope of waste management, it is possible to mention the byproducts of alcoholic fermentation, such as fusel oil, which is characterized as a mixture of alcohols formed during fermentation. Fusel oil is a mixture of short-chain branched and unbranched alcohols, mostly with 5 carbon atoms, with the main component being isoamyl alcohol. This alcohol can be obtained from fusel oil through fractional distillation, which can be used in various applications in the synthesis of other derivatives for multiple applications.

[0008] In this context, this application aims to reuse by-products from other production processes in order to obtain a compound of partially or entirely plant origin, renewable, biodegradable and with added value, as well as intended for personal care and household care formulations in general.

[0009] The state of the art reveals processes for reusing such by-products, as will be highlighted below.

[0010] Patent document GB 1095941 A describes a process for obtaining detergent compositions that comprises the simultaneous reaction of one or more active hydrogen organic compounds, one or more fatty acid esters, in which the fatty acids have 6 to 30 carbon atoms, esterified with one or more polyhydroxy alcohols and alkylene oxides. In this reference, tall oil (TOFA) is cited as an active hydrogen-containing organic compound and, therefore, does not qualify as a fatty acid ester. The reaction between the active hydrogen organic compound and the fatty acid occurs necessarily in the presence of an alkylene oxide, having 2 to 4 carbon atoms, and does not include isoamyl alcohol. The aforementioned document provides for only an aromatic alcohol in the reaction as described, thus obtaining a product different from that presented in this application.

[0011] Document US2022 / 0186149 Al discloses a composition comprising a plant resin material and one or more beneficiating agents, wherein said resin material is a plant resin ester material. The process for obtaining said document uses an alcohol containing 2 to 6 carbon atoms, in which said alcohol is selected from glycerol or pentaerythritol. It is important to highlight that the compound obtained in the document comprises at least two moles of ester group per mole of resin material.

[0012] Additionally, document WO2018222629 Al describes a composition comprising neutralized tall oil fatty acid, solvent, and water. However, said document presents fatty acid salts obtained from the neutralization reaction between tall oil and various neutralizing agents. It is important to emphasize that the chemical function of the fatty acid is maintained during the mixing process between the acid and the neutralizing agent, without the formation of new covalent bonds.

[0013] Finally, document US4822514 A discloses a cleaning composition comprising an alkali metal salt of a fatty acid, at least one alkanolamine salt of a fatty acid, a component selected from the group consisting of a fatty acid alkanolamide, an ethoxylated linear alcohol having 10 to 18 carbon atoms, a substituted ether, a compound selected from the group consisting of polyalkoxylated alkylalkane comprising ethoxy and propoxy groups, and their derivatives. It is important to note that the potassium salt of a fatty acid can be obtained from refined tall oil fatty acid. However, as previously explained, a tall oil fatty acid salt consists of a mixture of products, without the occurrence of change in the chemical function of the molecule or new covalent bonds between tall oil and an alcohol.

[0014] As can be seen, there remains a need in the state of the art for an ester compound, obtained from an esterification process using raw materials of partially or totally renewable origin, especially by-products from other production processes, which is easy to incorporate cold into formulations, especially aimed at the personal care and home care market. SUMMARY OF THE INVENTION

[0015] The present invention relates to an ester compound partially or entirely of renewable origin, as well as to the process for preparing the same, comprising the esterification between at least one alcohol of vegetable origin and at least one fatty acid. The esterification reaction occurs in the presence of a conventional catalyst or biocatalyst.

[0016] The present invention also relates to the use of the aforementioned ester compound for application in personal and household care formulations, for example as an emollient, solubilizer, hydrotrope, emulsifier, solvent, rheological modifier, among others, and to the personal or household care formulation itself. BRIEF DESCRIPTION OF THE FIGURES

[0017] Figure 1 illustrates a graph with the results of the spreadability tests performed by a texturometer.

[0018] Figure 2 illustrates a graph with the results of the spreadability tests (by dynamic contact angle in Vitro-Skin®).

[0019] Figures 3a, 3b and 3c illustrate the TGA analysis of a product obtained by the process of the present invention and comparative compounds.

[0020] Figure 4 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 5 illustrates a graph with the results of spreadability tests carried out using a texturometer on body cream samples.

[0022] Figure 6 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of sunscreen samples, measured using E95 Spindle, 2 RPM.

[0023] Figure 7 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of conditioner samples, measured using E95 Shaft, 2 RPM.

[0024] Figure 8 illustrates a graph with the values ​​obtained for the reduction in wet combing force.

[0025] Figure 9 illustrates a graph with the values ​​obtained for the reduction in dry combing strength.

[0026] Figure 10 illustrates a graph with the values ​​obtained for frizz reduction.

[0027] Figure 11 illustrates a graph with the values ​​obtained for brightness.

[0028] Figure 12 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of leave-in hair cream samples. DETAILED DESCRIPTION OF THE INVENTION

[0029] The search for renewable compounds, and therefore, with low environmental impact, is constant today, especially for compounds that act as emollients, solubilizers, hydrotropes, emulsifiers, solvents, rheological modifiers, and are easy to incorporate into formulations, such as personal care and home care formulations, such as surface care and laundry, for example.

[0030] In view of the above, in one embodiment, the present invention provides an ester compound having the following formula (I):

[0031] Wherein the radical Ri comprises from about 7 to about 21 carbon atoms, which may be saturated or unsaturated, linear or branched, more preferably from about 11 to about 19 carbon atoms, being saturated or unsaturated, linear or branched, even more preferably from about 15 to about 19 carbon atoms, being saturated or unsaturated, linear or branched, the most preferred being a resin acid selected from the group consisting of Tall OR (PITCH), distilled Tall OR and Tall OR fatty acids (or Tall OR Fatty Acid, TOFA) or mixtures thereof, wherein said fatty acids derived from black liquor from the pulp and paper industry also have resin acids in their composition and the concentration of said resin acids varies according to the raw material used and may vary from about 0.1% by weight to about 30% by weight, and wherein the radical R2 comprises between about 1 and about 22 carbon atoms,which may be saturated or unsaturated, linear or branched, preferably from about 5 to about 18 carbon atoms.

[0032] It is worth noting that the compound of the present invention has a partially or fully renewable origin, preferably fully renewable, since its fatty chain is not derived from traditional sources such as, for example, palm oil, palm kernel oil, coconut oil, sunflower oil, castor oil, soybean oil, castor oil, animal tallow, among others.

[0033] The compound in question has the property of being in a liquid or solid state, preferably liquid, at room temperature, which is advantageous for use in personal care and home care formulations. A compound with this technical characteristic allows for easy cold incorporation into formulations, taking its more sustainable applications, in addition to enabling a range of applications, presenting itself as an emollient, solubilizer of active ingredients, solubilizer of UV filters, hydrotrope, emulsifier, solvent, rheological modifier, softener, laundry detergent, among others, due to its low melting point, from approximately -50 °C to approximately 15 °C, which differentiates it from products already existing in the state of the art for such application.

[0034] In another embodiment, the present invention relates to the process of preparing an ester compound comprising the esterification reaction that allows, from vegetable raw materials, to obtain a partially or totally renewable compound.

[0035] Such raw materials comprise at least one alcohol and at least one fatty acid of plant origin, partially or fully renewable and biodegradable. The at least one fatty acid is preferably a fatty acid byproduct of the kraft pulping process of wood in the pulp and paper industry, which is characterized by being a product rich in fatty acids with saturated or unsaturated, linear or branched, alkyl chains of approximately C12 to C22, preferably alkyl chains of approximately C16 to C20, and may be a mixture of fatty acids containing resin acids, among other compounds.

[0036] Said at least one fatty acid can be characterized by formula (II): where Ri is a radical comprising between about 7 and about 21 carbon atoms, preferably between about 11 and about 19 carbon atoms, more preferably between about 15 and about 19 carbon atoms, and may be saturated and / or unsaturated, branched and / or linear.

[0037] Even more preferably, the fatty acid by-product of the kraft pulping process of wood in the pulp and paper industry is Tall OR resin acid (PRES) or distilled Tall OR or Tall OR fatty acids (or Tall OR Fatty Acid, TOFA) or mixtures thereof.

[0038] In one embodiment, the fatty acid may be partially or wholly derived from traditional sources such as palm oil, palm kernel oil, coconut oil, sunflower oil, castor oil, soybean oil, castor oil, animal tallow, among other similar sources or mixtures thereof.

[0039] The at least one vegetable alcohol employed in the esterification process of the present invention is selected from alcohols comprising from about 1 to about 22 carbon atoms, saturated or unsaturated, linear or branched, preferably from about 5 to about 18 carbon atoms, more preferably an alcohol originating from the alcoholic fermentation process. Particularly, the at least one vegetable alcohol can 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 most preferred. 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-1-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.

[0040] In a preferred embodiment of the invention, the ester compound is isoamyl thalate.

[0041] The esterification process comprises the reaction between at least one fatty acid and at least one alcohol in molar proportions of acid of about 0.5 to about 1.0 mol and alcohol of about 0.8 to about 1.5, preferably in a molar ratio of about 1.0 fatty acid to 1.3 alcohol.

[0042] The esterification reaction between at least one fatty acid and at least one vegetable alcohol occurs via homogeneous or heterogeneous, organic or inorganic catalysis, in the presence of catalysts that may be conventional, preferably conventional acid catalysts, more preferably an organic acid, or biocatalysts.

[0043] The said esterification process occurs at a temperature in the range of approximately 60°C to approximately 180°C, more specifically between approximately 105°C and 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 5 and approximately 7 hours.

[0044] The esterification process also includes product neutralization steps and subsequent drying and purification steps by removing excess alcohol. The product neutralization step involves the use of a suitable alkaline solution with agitation. Subsequent drying and purification steps involve removing excess unreacted alcohol during the reaction using a vacuum system of approximately 100 to approximately 200 mmHg and a temperature between 125°C and 135°C.

[0045] Thus, the esterification process of the present invention specifically comprises the steps of obtaining at least one fatty acid from the kraft pulping process of wood in the paper and cellulose industry, obtaining at least one vegetable alcohol comprising a carbon chain from C1 to C22, preferably C5 to Cis, and reacting them in the presence of an acid catalyst, selected from the group consisting of methanesulfonic acid, para-toluenesulfonic acid, xylenesulfonic acid, phosphoric, sulfuric acid, among others, or mixtures thereof, preferably methanesulfonic acid combined with hypophosphorous acid, or biocatalyst, to obtain the ester compound of partially or totally renewable origin of the present invention as previously described herein.

[0046] The use of biocatalysts enables milder reaction conditions of temperature and pressure compared to conventional acid catalysts, allowing the process to be more economical, more environmentally sustainable and with greater preservation of the integrity of thermosensitive compounds.

[0047] It's worth noting that biocatalysts come from renewable sources, such as microorganisms, enzymes, and plants, and therefore, their use reduces dependence on fossil-fuel-based raw materials. Additionally, biocatalysts are biodegradable and do not generate solid waste, contributing to a more sustainable process.

[0048] In the case of enzymes, it's important to note that many are active in aqueous environments, thus enabling esterification reactions without the use of potentially toxic solvents, reducing safety risks and minimizing environmental impact. Furthermore, biocatalysts can be regenerated through chemical reactions and reused, increasing the economic efficiency of the process in which they are applied.

[0049] Nevertheless, biocatalysts can exhibit significant selective behavior (chemo-, regio-, and stereoselectivity), providing precise control over the desired ester product and being especially advantageous when working with complex substrates or when specific stereochemistry is required.

[0050] In one embodiment of the present invention, said biocatalyst is selected from a group comprising lipases, proteases, amylases, cellulases, pectinases, catalases, isomerases, preferably lipases or mixtures thereof.

[0051] 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 preferably used, 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 of about 1.0:1.0 to about 1.0:1.5 being preferably used, also presenting the advantages of separating the biocatalyst from the reaction medium by simple filtration and there being no need for a neutralization step.

[0052] In another embodiment, the present invention relates to the use of an ester compound of partially or fully renewable origin of the present invention in formulations such as emollient, active ingredient solubilizer, UV filter solubilizer, hydrotrope, emulsifier, solvent, rheological modifier, softener, laundry detergent, among others in personal care formulations, as well as household care involving clothing and fabric care, in addition to formulations for skin or hair applications in general, as well as in makeup, deodorant, antiperspirant, conditioner, shampoo, hair or skin creams, face cleanser, sunscreen, liquid soap, bar soap, shower gel, among other applications for personal or household care in general.

[0053] In a further embodiment, the present invention is also directed to a personal or home care formulation comprising from about 0.1% to about 99.5% by weight or more of the compound of formula (I), based on the total weight of the formulation, together with one or more adjuvant agents.

[0054] Said one or more adjuvant agents are selected from the group consisting of preservatives, thickeners, colorants, perfume or fragrance, cleaning actives and / or whitening agents. In addition, the formulations described herein may also comprise adjuvants commonly used in washing, cleaning and cosmetic products selected from the group consisting of foam promoters, emollients, pH regulators, sequestrants, among others.

[0055] Said additional adjuvant agents may be present in an amount of about 0.1% to 99.5% by weight, based on the total weight of the formulation. EXAMPLES Example 1

[0056] 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. 286 g of TOFA fatty acid is reacted with 114.6 g of isoamyl alcohol in the presence of 0.1% by mass methanesulfonic acid as a catalyst under a N2 atmosphere at 110°C for 6 hours. After the esterification step, the product is purified under a 200 mmHg vacuum with heating at 100°C for 2 hours. The product then undergoes a neutralization step initiated by a pre-wash with distilled water, followed by neutralization with a 30% sodium carbonate solution, and then washing with distilled water. A product drying step is performed by subjecting the reaction system to a 200 mmHg vacuum with heating at 90°C for 4 hours. Finally, the product is vacuum filtered at room temperature. Example 2 - Spreadability Example 2a

[0057] Next, a spreadability test was performed, using a texture analyzer (TA-XT Plus) to apply force to the sample to expel it from the sample cup. In this case, the lower the force required, the greater the spreadability.

[0058] As can be seen in Figure 1, the result obtained for the The ester obtained by the process of the present invention (isoamyl tallate) was equivalent to benchmarks such as dicaprylyl carbonate and coconut caprylate / caprate. Furthermore, isoamyl tallate was superior to dimethicone 200 / 350 and isopropyl palmitate, emollients whose origin is not 100% renewable. It was also superior to caprylic / capric triglyceride, which is 100% renewable but can be derived from palm oil, unlike isoamyl tallate, which is free of palm derivatives. Example 2b

[0059] Additionally, a spreadability test was performed on Vitro-Skin®, a synthetic skin substrate that mimics the surface properties of human skin. It has similar topography, pH, critical surface tension, chemical reactivity, and ionic strength to human skin, making it ideal for in vitro testing where human skin is required.

[0060] The procedure was as follows: - Substrate preparation. - Application of emollient to the substrate (10pl) - 10 min wait - Sprinkling talcum powder on the substrate - Area measurement using graph paper or imaging software.

[0061] Figure 2 shows the spreadability graph (by dynamic contact angle in Vitro-Skin®).

[0062] In this graph, the lower the contact angle, the better the wetting or spreading. Emollients with lower spreadability require more time to reach complete spreading / absorption (contact angle = 0).

[0063] Isoamyl thalate exhibited superior spreadability compared to dimethicone 200 / 350, caprylic / capric triglyceride, and liquid paraffin, and was equivalent to dicaprylyl carbonate, palmitate, isopropyl and coco-caprylate caprate.

[0064] The polarity of the tested compounds was also verified, as shown in Table 1. Table 1: Polarity of tested samples 'The sample did not present a Newtonian profile and did not form a drop at the tip of the needles available for analysis. * Calculated by subtracting the interfacial tension of the emollient-water interface from the surface tension of the water-air interface = 72 mN.m.

[0065] According to Table 1, isoamyl thalate is the most polar of the samples, which is consistent with its low interfacial tension. Liquid paraffin (mineral oil) is the least polar, reflecting its lower affinity for water.

[0066] The greater polarity of isoamyl thalate suggests good affinity for aqueous systems and potential to act as a light emollient and co-surfactant in formulations.

[0067] 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 3a, 3b, and 3c illustrate graphs with the results of the TGA analysis. The lower the degradation temperature, the more susceptible the product is to thermal degradation.

[0068] 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

[0069] Body cream samples were prepared with 5% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl thalate). The remaining samples were prepared with 5% of comparative compounds as emollients, namely: caprylic / capric triglyceride, coconut caprylate / caprate, cocos nucifera oil, dicaprylyl carbonate, liquid paraffin, isopropyl palmitate and cyclopentasiloxane.

[0070] Figure 4 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.

[0071] The body cream with isoamyl thalate had a higher viscosity than all other formulations, including the formulation without emollient, and similar to the formulation containing cocos nucifera oil, which is a solid at 25°C.

[0072] 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

[0073] The samples above have the following emollients: F02 - cyclopentasiloxane; F37 - no emollient; F38 - caprylic / capric triglyceride; F39 - coco-caprylate / caprate; F40 - cocos nucifera oil; F41 - dicaprylyl carbonate; F42 - liquid paraffin; F43 - isopropyl palmitate; F44 - isoamyl cocoate; F47 - isoamyl thalate.

[0074] Figure 5 illustrates a graph with the results of the spreadability tests carried out using a texturometer on the body cream samples.

[0075] The lower the strength, the easier it is to spread. This means that the F02 formulation with cyclopentasiloxane had the best spreadability of all the emollients, and the results with isoamyl tallate are comparable to other emollients on the market.

[0076] Furthermore, the body cream with isoamyl thalate showed superior spreadability compared to the formulation containing cocos nucifera oil, even though it had a similar viscosity to the formulations with cocos nucifera oil. Sunscreen

[0077] Sunscreen samples were prepared with 8% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl thalate). The remaining samples were prepared with 8% of comparative compounds as emollients, namely: C12-15 alkyl benzoate; caprylic / capric triglyceride; coco-caprylate / caprate; cocos nucifera oil; dicaprylyl carbonate; liquid paraffin; isopropyl palmitate.

[0078] Figure 6 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.

[0079] The sunscreen with isoamyl thalate presented a lower, but still acceptable, viscosity compared to formulations containing other emollients commonly used in this product category. Hair conditioner

[0080] Hair conditioner samples were prepared with 1% of different emollients, including an emollient obtained by the esterification process of the present application (isoamyl thalate). The remaining samples were prepared with 1% of comparative compounds as emollients, namely: cocos nucifera oil; dimethicone; liquid paraffin; isopropyl palmitate; caprylic / capric triglyceride; dimethicone 200 / 350; and cyclopentasiloxane.

[0081] Figure 7 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.

[0082] The hair conditioner with isoamyl thalate showed similar viscosity to the formulations containing cocos nucifera oil, liquid paraffin, caprylic / capric triglyceride and cyclopentasiloxane (D5).

[0083] All prepared conditioner samples showed stability for 90 days at 5, 25 and 40 °C, without phase separation.

[0084] Figure 8 illustrates a graph with the values ​​obtained for the reduction in wet combing force.

[0085] As can be seen, isoamyl tallate presented a result equivalent to isopropyl palmitate and blank (without emollient), superior to cocos nucifera oil and inferior to dimethicone 60,000.

[0086] Figure 9 illustrates a graph with the values ​​obtained for the reduction in dry combing strength.

[0087] Isoamyl thalate presented a result equivalent to isopropyl palmitate and inferior to dimethicone 60,000.

[0088] Figure 10 illustrates a graph with the values ​​obtained for frizz reduction.

[0089] Isoamyl tallate showed results equivalent to isopropyl palmitate and dimethicone 60,000 and superior to coconut oil nucifera.

[0090] Figure 11 illustrates a graph with the values ​​obtained for brightness.

[0091] Isoamyl thalate was numerically superior but statistically equivalent to the other emollients. Leave-in hair cream

[0092] 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 thalate). The remaining samples were prepared with 1% of comparative compounds as emollients, namely: cocos nucifera oil; dimethicone 60000; liquid paraffin; isopropyl palmitate; caprylic / capric triglyceride; dimethicone 200 / 350.

[0093] Figure 12 illustrates a graph with the values ​​obtained for Brooksfield Viscosity (BKF) in mPa.s of the leave-in hair cream samples.

[0094] The leave-in hair cream with isoamyl tallate had a viscosity similar to that of formulations containing cocos nucifera oil and liquid paraffin, and slightly better than the two types of dimethicone tested: medium and high viscosity. It performed worse than the blank, isopropyl palmitate, and caprylic / capric triglyceride, but was still acceptable.

[0095] It can be seen from the examples and information provided herein that the present invention advantageously provides an environmentally friendly, partially or fully renewable ester compound, preferably liquid at room temperature, which allows its cold incorporation into personal and household care formulations, in addition to having a low melting point between approximately -50°C and 15°C, unlike UV filter solubilizers currently on the market. Furthermore, because it comes from renewable raw materials, its production process allows the reuse / recovery of waste from other production processes, generating products with added value through a route that is favorable both for the environment and for economic development, enabling their use in various applications that are no longer limited to personal and household care formulations.

[0096] Such processes, products, and uses have not been suggested nor are they evident from the published literature on the subject.

[0097] 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 of renewable origin, characterized by the fact that formula (I): in which the radical Ri comprises between about 7 and about 21 carbon atoms, being saturated or unsaturated, linear or branched, and in which the radical R2 comprises between about 1 and about 22 carbon atoms, and may be saturated or unsaturated, linear or branched.

2. Compound according to claim 1, characterized in that the ester compound is partially of renewable origin or entirely of renewable origin.

3. Compound according to claim 1 or 2, characterized by the fact that it is liquid or solid.

4. Compound according to any one of claims 1 to 3, characterized in that the radical Ri preferably comprises between about 11 and about 19 carbon atoms, more preferably between about 15 and about 19 carbon atoms.

5. Compound according to any one of claims 1 to 4, characterized in that the radical R2 preferably comprises from about 5 to about 18 carbon atoms.

6. Compound according to any one of claims 1 to 5, characterized in that the radical Ri is a resin acid selected from the group consisting of Tall Oil, Tall OU distillate and Tall OU fatty acids (TOFA) or mixtures thereof.

7. Compound according to any one of claims 1 to 6, characterized in that the radical Ri is of plant origin, REPLACEMENT SHEET (RULE 26) renewable and biodegradable.

8. Compound according to claim 1, characterized in that the ester compound is isoamyl thalate.

9. Process for the preparation of an ester compound, characterized by the fact that it comprises the steps of: i) obtaining at least one fatty acid from the kraft pulping process of wood in the paper and cellulose industry comprising from approximately 12 to 22 carbon atoms, saturated or unsaturated, linear or branched of formula (II): where Ri is a radical comprising between about 7 and 21 carbon atoms; ii) obtaining at least one vegetable alcohol comprising from about 1 to 22 carbon atoms, saturated or unsaturated, linear or branched, iii) reacting the at least one alcohol obtained in step ii) with the at least one fatty acid of step i) in the presence of a catalyst, at a temperature of about 60°C to about 180°C, wherein the reaction system comprises a Dean-Stark apparatus; wherein the molar ratio between the at least one fatty acid and the at least one alcohol is about 0.5 to about 1.0 mole of acid for every about 0.8 to about 1.5 mole of alcohol, iv) obtaining an ester compound of renewable origin of the formula d): REPLACEMENT SHEET (RULE 26) in which the radical Ri comprises between about 7 and 21 carbon atoms, being saturated or unsaturated, linear or branched, and in which the radical R2 comprises between about 1 and about 22 carbon atoms, and may be saturated or unsaturated, linear or branched.

10. Process according to claim 9, characterized in that the reaction is maintained for a period of about 1 to about 10 hours, preferably between about 5 and about 7 hours.

11. The process of claim 9, wherein the at least one fatty acid preferably comprises about 16 to about 20 carbon atoms.

12. Process according to claim 9, characterized in that the at least one vegetable alcohol preferably comprises about 5 to about 18 carbon atoms.

13. Process according to any one of claims 9 to 12, characterized in that the fatty acid and the alcohol are present in acid:alcohol molar ratios ranging from about 1:1 to about 1:2.2, preferably from about 1.0:1.0 to about 1.0:1.

5.

14. Process according to any one of claims 9 to 13, characterized in that the fatty acid originating from a by-product of the kraft pulping process of wood is a resin acid selected from the group consisting of Tall OU (PITCH), distilled Tall OU and Tall OU fatty acids (or Tall OU Fatty Acid, TOFA), among others, or mixtures thereof, in which the fatty acids may comprise between about 0.1% by weight to about 30% by weight of resin acids.

15. Process according to any one of claims 9 to 14, characterized in that at least one fatty acid can come from traditional sources such as palm oil, palm kernel oil, coconut oil, sunflower oil, castor oil, soybean oil, castor oil, tallow REPLACEMENT SHEET (RULE 26) animal, among other similar sources and their mixtures.

16. Process according to any one of claims 9 to 15, characterized in that the at least one alcohol resulting from the alcoholic fermentation process is 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, 3-methyl-1-butanol or isoamyl alcohol, being the most preferable, in addition to the isoamyl alcohol isomers, the 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-1-butanol or isoamyl alcohol. -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.

17. Process according to any one of claims 9 to 16, characterized in that the catalyst is an organic or inorganic catalyst, homogeneous or heterogeneous, in which said catalyst is selected from the group comprising methanesulfonic acid, para-toluene sulfonic acid, xylene sulfonic acid, phosphoric acid and sulfuric acid or mixtures thereof.

18. Process according to any one of claims 9 to 17, characterized in that the catalyst is a biocatalyst selected from the group comprising lipases, proteases, amylases, cellulases, pectinases, catalases and isomerases or mixtures thereof.

19. Process according to any one of claims 9 to 18, characterized in that, when a biocatalyst is used, the reaction occurs in a temperature range of about 40°C to about 80°C for a period of about 5 to about 10 hours of reaction, with a molar ratio of REPLACEMENT SHEET (RULE 26) acid: alcohol ranging from approximately 1:1 to approximately 1:2.2, and in which the biocatalyst is separated from the reaction medium by simple filtration, without neutralization.

20. Process according to any one of claims 9 to 19, characterized in that it further comprises the steps of neutralizing, drying and purifying the product, in which the neutralizing step comprises the use of a suitable alkaline solution with agitation of the medium, and in which the subsequent steps of drying and purifying the final product comprise the removal of excess unreacted alcohol during the reaction using a system with a vacuum of about 100 to about 200 mmHg and a temperature of about 125°C to about 135°C.

21. Use of a compound as defined in any one of claims 1 to 8, characterized in that it is in a personal or household care formulation.

22. Use according to claim 21, characterized by the fact that it is in formulations for applications for skin or hair in general, such as makeup, deodorant, antiperspirant, conditioner, shampoo, hair or skin creams, face cleanser, sunscreen, liquid soap, bar soap, shower gel, or in formulations of laundry detergent, fabric softener, among other applications for personal or household care.

23. Use according to claim 21 or 22, characterized by the fact that it is an emollient, solubilizer of active ingredients, solubilizer of UV filters, hydrotrope, emulsifier, solvent, rheological modifier, softener, laundry detergent, among others.

24. Personal or household care formulation, characterized by the fact that it comprises about 0.1% to 99.5% or more of the REPLACEMENT SHEET (RULE 26) compound of formula (I) based on the total weight of the formulation and adjuvant agents, in which the radical Ri comprises between approximately 7 and 21 carbon atoms, being saturated or unsaturated, linear or branched, and in which the radical R2 comprises between approximately 1 and approximately 22 carbon atoms, and may be saturated or unsaturated, linear or branched.

25. Formulation according to claim 24, characterized in that the additional adjuvant agents are selected from the group consisting of preservatives, thickeners, colorants, perfume or fragrance, cleaning actives and / or whitening agents, foam promoters, emollients, pH regulators, sequestrants, among others.

26. Formulation according to claim 24 or 25, characterized in that the additional adjuvants are present in a concentration of about 0.1% to 99.5% by weight based on the total weight of the formulation. REPLACEMENT SHEET (RULE 26)

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