Branched fatty acids and esters thereof

Abstract

To provide compositions of branched fatty acids or esters thereof exhibiting improved low-temperature properties.SOLUTION: The present invention provides a composition of branched C10-C24 fatty acids or esters thereof, comprising at least 30 wt.% of polybranched C10-C24 fatty acids or esters thereof, and 1-8 wt.% of a cyclic compound, the weight percentage being given on the total weight of the composition.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a composition containing a branched fatty acid or an ester thereof, a method for preparing such a composition, and their uses in various industrial fields such as lubricants, personal care products, and compositions for home care products.

Background Art

[0002] Commercially available branched fatty acids such as "isostearic acid" are obtained as by-products of the catalytic dimerization and thermal dimerization of linear unsaturated fatty acids. Dimer acids and higher oligomeric acids are produced by heating unsaturated fatty acids in the presence of a catalyst. However, instead of oligomerizing, some of the fatty acids rearrange to produce branched monomeric fatty acids that can be isolated from the oligomerized fatty acids. The branched fatty acid composition commercially available as this "isostearic acid" is a mixture of various linear saturated monocarboxylic acids and mainly branched saturated monocarboxylic acids (both mono-branched and multi-branched).

[0003] In recent years, the focus has shifted to optimizing the production of these branched monomeric fatty acids, which are no longer considered by-products. In particular, esters derived from "isostearic acid" are widely used in lubricating oils and cosmetic compositions. European Patent Application Publication No. 2702127 describes a method for producing a mono-branched fatty acid through the isomerization of an unsaturated C 10 -C 26 fatty acid in the presence of a catalyst containing both a zeolite and a Lewis base.

Summary of the Invention

[0004] The applicant of the present application has surprisingly found that a composition having a high content of multi-branched C 10 -C 24 fatty acid or an ester thereof and a reduced content of cyclic compounds provides better low-temperature properties, particularly better low-temperature properties with respect to its cloud point and pour point. The foregoing prior art documents do not teach regarding the content of this cyclic compound.

[0005] Accordingly, the present invention relates to a composition having a high content of a multi-branched fatty acid or its ester and a low content of a cyclic compound.

[0006] More specifically, the present invention relates to a composition of a branched C 10 -C 24 fatty acid or its ester, comprising: at least 30% by weight of a multi-branched C 10 -C 24 fatty acid or its ester, and 1 to 8% by weight of a cyclic compound wherein the % by weight is given relative to the total weight of the composition.

[0007] In the present specification, unless otherwise indicated, all value ranges used are understood to be inclusive limitations.

[0008] Advantageously, the composition of the present invention is more stable. Advantageously, the composition of the present invention is a multi-branched fatty acid with few cyclic compounds and is liquid at 0°C. This composition is also stable at high temperatures and resistant to ultraviolet light. Advantageously, the composition of the present invention exhibits better low-temperature properties. The pour point of the composition of the branched C 10 -C 24 fatty acid ester can be less than -40°C, lower than the pour point of the corresponding ester as shown in Example 2 obtained from a commercially available composition of branched fatty acids.

[0009] Here, the "branched" fatty acid means that the hydrocarbon chain of the monocarboxylic acid generally has one or more short alkyl side groups. Here, the "short alkyl side group" means a group containing 5 or fewer carbon atoms. More preferably, each short alkyl side group is linear, and even more preferably, it is selected from the group consisting of a methyl group, an ethyl group, and a propyl group. Preferably, each short alkyl side group is a methyl group and / or an ethyl group, and more preferably a methyl group.

[0010] Here, "branched C 10 -C 24 fatty acid or its ester" means a multi-branched C 10 -C 24 fatty acid, or a multi-branched C 10 -C 24 ester of a fatty acid, optionally, a mono-branched C 10 -C 24 fatty acid, or a mono-branched C 10 -C 24 ester of a fatty acid, respectively. Here, the "mono-branched" fatty acid means that the straight-chain hydrocarbon chain of the fatty acid generally has only one short alkyl side group. Here, the "multi-branched" fatty acid means that the straight-chain hydrocarbon chain of the fatty acid generally has two or more short alkyl side groups.

[0011] The "C X " in the term indicates the number of carbon atoms in the fatty acid, that is, the number of carbon atoms in the hydrocarbon chain plus the number of carbon atoms in any one or more alkyl side groups. Therefore, "branched C X " refers to all branched fatty acids having X carbon atoms. In particular, these branched fatty acids are positional isomers. The "C X -C Y fatty acid, or its ester" means that the number of carbon atoms in each fatty acid is independently composed between X and Y.

[0012] The multi-branched fatty acid or its ester is a saturated monocarboxylic acid or its ester. Preferably, the multi-branched C 10 -C 24 fatty acid or its ester is a multi-branched C 14 -C 22 fatty acid or its ester, more preferably a multi-branched C 16 -C 18 fatty acid or its ester.

[0013] In a specific embodiment, the branched C according to the present invention10 -C 24 The composition of the fatty acid or its ester contains at least 30% by weight of a multi-branched C 18 fatty acid or its ester, based on the total weight of the composition. Preferably, the composition contains at least 32% by weight, more preferably at least 34% by weight of a multi-branched C 10 -C 24 fatty acid or its ester, based on the total weight of the composition.

[0014] C 10 -C 24 The ester of the fatty acid may be a monoester or a polyester. In fact, the ester composition according to the present invention can be obtained by esterifying an alcohol with a C 10 -C 24 fatty acid composition, where the alcohol may be a monohydroxyl compound, a polyhydroxyl compound, or a mixture thereof. Preferably, the alcohol consists of a saturated straight-chain or branched hydrocarbon chain containing one or more hydroxyl groups.

[0015] "Cyclic compounds" include, but are not limited to, alicyclic carboxylic acids or their esters, aromatic compounds, alkylcyclopentanones, lactones, and mixtures thereof.

[0016] "Alicyclic carboxylic acid or its ester" means a molecule containing one carboxylic acid or ester functional group, one cyclic hydrocarbon, and one or more straight-chain hydrocarbons. Preferably, the alicyclic carboxylic acid or its ester is a saturated compound. Preferably, the cyclic hydrocarbon is a cyclopentyl compound or a cyclohexyl compound. More preferably, the alicyclic carboxylic acid or its ester is the one shown in Structural Formula (I) and / or Structural Formula (II).

[0017]

Chemical formula

[0018] [Chemical formula]

[0019] Here, R 1 is a hydrocarbon chain containing 0 to 18, preferably 0 to 12 carbon atoms; R 3 is a hydrocarbon chain containing 0 to 17, preferably 0 to 11 carbon atoms; R 2 is hydrogen or a hydrocarbon chain finally substituted with a hydroxyl group or an ester functional group; m is an integer included in the range of 0 to 18, preferably 1 to 12; n is an integer included in the range of 0 to 17, preferably 1 to 11.

[0020] Aromatic compounds include, but are not limited to, phenylcarboxylic acids or their esters. "Phenylcarboxylic acid, or its ester" means a molecule containing a carboxylic acid or ester functional group and a phenyl group. Specifically, the phenylcarboxylic acid or its ester is as shown in structural formula (III).

[0021] [Chemical formula]

[0022] Here, R 3 is a hydrocarbon chain containing 0 to 17, preferably 0 to 11 carbon atoms; R 2 is hydrogen or a hydrocarbon chain finally substituted with a hydroxyl group or an ester functional group; n is an integer included in the range of 0 to 17, preferably 1 to 11.

[0023] More specifically, the phenylcarboxylic acid or its ester is as shown in structural formula (III), where R 1is a hydrocarbon chain containing 3 carbon atoms, and n is 9. Preferably, the cyclic compound contains 14 to 22 carbon atoms, more preferably 16 to 18 carbon atoms.

[0024] Preferably, the content of the cyclic compound is 1% to 6% by weight, more preferably 3% to 5% by weight, based on the total weight of the composition. Preferably, the cyclic compound of the composition of the present invention contains an alicyclic carboxylic acid or its ester, and the content thereof is 0.5% to 6% by weight based on the total weight of the composition. Advantageously, the content of the alicyclic carboxylic acid or its ester is 0.5% to 4% by weight, more preferably 0.5% to 3% by weight, and even more preferably 1% to 2.5% by weight, based on the total weight of the composition.

[0025] Advantageously, the content of the aromatic compound in the composition according to the present invention is less than 3% by weight, preferably less than 2.5% by weight, more preferably less than 2.3% by weight, and even more preferably less than 2% by weight, based on the total weight of the composition. Typically, the composition of the present invention contains 0.2% to 2.3% by weight, more preferably 0.2% to 1.8% by weight of aromatic compounds, based on the total weight of the composition.

[0026] Preferably, the content of alkylcyclopentanone is less than 1% by weight, more preferably less than 0.6% by weight, based on the total weight of the composition. Preferably, the content of lactone is less than 2% by weight, more preferably less than 1.5% by weight, and even more preferably less than 1% by weight, based on the total weight of the composition.

[0027] Advantageously, the composition of the present invention contains at least 15% by weight of monobranched C 10 -C 24 fatty acid or its ester. The monobranched fatty acid or its ester is a saturated monocarboxylic acid or its ester. Preferably, the composition according to the present invention contains at least 25% by weight, more preferably at least 30% by weight, of monounsaturated C 10 -C 24 fatty acid or its ester, based on the total weight of the composition.

[0028] Preferably, the monounsaturated C 10 -C 24 fatty acid or its ester is a monounsaturated C 14 -C 22 fatty acid or its ester, and more preferably, it is a monounsaturated C 16 -C 18 fatty acid or its ester. In particular, the composition according to the present invention contains at least 15% by weight of monounsaturated C 18 fatty acid or its ester, based on the total weight of the composition. Advantageously, the weight ratio of the monounsaturated form to the polyunsaturated form of the branched C 18 fatty acid or its ester in the composition of the present invention is 0.5 to 1.5. Preferably, the weight ratio is 0.5 to 1.4, and more preferably, it is 0.6 to 1.3.

[0029] Advantageously, the composition of the present invention contains at least 50% by weight of monounsaturated and polyunsaturated C 10 -C 24 fatty acid, or its ester, based on the total weight of the composition. Preferably, the composition of the present invention contains at least 60% by weight, more preferably at least 70% by weight, and even more preferably at least 80% by weight of monounsaturated and monounsaturated C 10 -C 24 fatty acid, or its ester, based on the total weight of the composition.

[0030] In a specific embodiment, the composition contains at least 60% by weight, preferably at least 68% by weight, and more preferably at least 70% by weight of monounsaturated and polyunsaturated C 18 fatty acid, or its ester, based on the total weight of the composition.

[0031] Advantageously, the composition of the present invention further comprises 1 to 25% by weight, based on the total weight of the composition, of a linear saturated C8-C 24 fatty acid or an ester thereof. Preferably, the content of the linear C8-C 24 fatty acid or an ester thereof is 1% to 20% by weight, more preferably 5% to 18% by weight, based on the total weight of the composition. Preferably, the composition according to the present invention comprises less than 18% by weight, preferably less than 16% by weight, of linear C 16 fatty acid or an ester thereof, based on the total weight of the composition.

[0032] In a preferred embodiment, the composition of the present invention is as follows: 30 to 60% by weight of a multi-branched C 10 -C 24 fatty acid or an ester thereof; 15 to 50% by weight of a mono-branched C 10 -C 24 fatty acid or an ester thereof; 5 to 18% by weight of a linear C8-C 24 fatty acid or an ester thereof; 0.5 to 3% by weight of an alicyclic carboxylic acid or an ester thereof; comprising wherein the % by weight is relative to the total weight of the composition wherein the weight ratio of the mono-branched / multi-branched of the branched C 18 fatty acid or an ester thereof is from 0.5 to 1.5, preferably from 0.6 to 1.3.

[0033] In a particularly preferred embodiment, the composition of the present invention is as follows: 30 to 40% by weight of a multi-branched C 18 fatty acid or an ester thereof; 25 to 45% by weight of a mono-branched C 18 fatty acid or an ester thereof; 4 to 18% by weight of a branched C 16 fatty acid or an ester thereof; 5 to 18% by weight of a linear C8-C 24 fatty acid or an ester thereof; 0.5 to 3% by weight of an alicyclic carboxylic acid or its ester; comprising, wherein the % by weight is based on the total weight of the composition, wherein the weight ratio of the monobranched / multibranched of the branched C 18 fatty acid or its ester is from 0.5 to 1.5, preferably from 0.6 to 1.3.

[0034] This particularly preferred embodiment of the composition of the present invention exhibits very good low temperature properties. More preferably, the cloud point is less than 5°C, more preferably less than 3°C. The cloud point refers to the temperature below which the composition exhibits solid particles, and since the solid particles can result in an undesirable appearance for the consumer and can lead to clogging of small holes, it is advantageous to provide a composition with a low cloud point. In contrast, a commercial composition of a branched fatty acid such as Radiacid 0907 manufactured by Oleon has a cloud point of about 7°C as determined by the method of AOCS Cc 6-25.

[0035] The present invention also relates to a method for preparing a branched C 10 -C 24 fatty acid composition from a starting material containing at least 70% by weight of a linear monoethylenically unsaturated C 10 -C 24 fatty acid, comprising the following steps: i) isomerizing the linear monoethylenically unsaturated C 10 -C 24 fatty acid from the starting material by heating in the presence of a clay catalyst, and ii) separating the monomer fraction from the oligomer fraction formed during step i), iii) purifying the monomer fraction to obtain a branched C 10 -C 24 fatty acid composition.

[0036] Advantageously, by the method for preparing a branched C 10 -C 24 fatty acid composition according to the present invention, a multibranched C 10 -C24 A composition with a high fatty acid content and a low cyclic compound content can be obtained.

[0037] Step i) is carried out at a temperature sufficient to achieve the isomerization reaction. The isomerization step may be carried out in a temperature range of 150 °C to 300 °C, preferably 180 °C to 260 °C, and in a pressure range of 1 bar(G) to 10 bar(G), preferably 2 bar(G) to 8 bar(G). "bar(G)" refers to the unit of gauge pressure measurement. The isomerization step may be carried out for 1 hour to 8 hours, preferably 2 hours to 5 hours. The isomerization step may be carried out in the presence of water, and the water content is preferably 0.1 to 5% by weight based on the total weight of the starting materials.

[0038] Advantageously, in the method for preparing the composition according to the present invention, the isomerization step may be carried out in the presence of an alkali metal salt up to 0.5% by weight, where the % by weight is given relative to the total weight of the starting materials. The isomerization conditions enable the monomer fraction to be obtained in a yield of 40% to 70%, preferably 55% to 70%.

[0039] Subsequent to the isomerization step, a step of treating with an inorganic acid, preferably phosphoric acid, may further be carried out. Subsequent to the isomerization step, the method may further include a step of separating the clay catalyst from the reaction product of step i), preferably by filtration.

[0040] Step ii) is preferably achieved by distillation, particularly molecular distillation, at a temperature of 200 to 300 °C and a pressure of 1 to 4 mbar.

[0041] Step iii) may include hydrogenation, crystallization, and / or distillation.

[0042] Hydrogenation can be carried out by methods known in the art, for example, using palladium on carbon or supported nickel as a catalyst. Preferably, the temperature during hydrogenation is 180 to 250 °C and the pressure is 15 to 25 bar(G). Crystallization may be carried out using sulfates or urea (clathrate method) to separate the solidified linear fatty acids of the product from the liquid branched fatty acids. Distillation is preferably carried out at a temperature of 200 to 300 °C and a pressure of 1 to 4 mbar.

[0043] After step iii), a branched C 10 -C 24 fatty acid composition is obtained. Specifically, the composition contains at least 30% by weight of multi-branched C 10 -C 24 fatty acids and 1 to 8% by weight of cyclic compounds based on the total weight of the composition. Linear, branched, mono-branched, and multi-branched C 10 -C 24 fatty acids, as well as cyclic compounds, are as described above, including preferred and advantageous positions.

[0044] The starting material is preferably a fatty acid of renewable oil. The renewable oil is preferably a vegetable oil or an animal oil.

[0045] Some renewable oils naturally contain at least 70% by weight of linear monoethylenically unsaturated C 10 -C 24 fatty acid groups. The corresponding fatty acids can be recovered from any of these oils by any method known in the art. Suitable renewable oils are high oleic acid sunflower oil, oleic acid safflower oil, crambe oil, lunaria oil, olive oil. Preferably, the starting material is a fatty acid obtained from high oleic acid sunflower oil, oleic acid safflower oil, or crambe oil.

[0046] While being mono- and polyethylenically unsaturated compounds, linear monoethylenically unsaturated C 10 -C 24 Renewable oils having a fatty acid group content of less than 70% by weight based on the weight of the renewable oil may be partially hydrogenated to optimize their content before recovering the corresponding fatty acids. Renewable oils suitable for partial hydrogenation are rapeseed oil, corn oil, soybean oil, sunflower oil, safflower oil, tall oil.

[0047] Fatty acids obtained from any renewable oil may be isolated and fractionated to obtain a suitable starting material. 10 -C 24 The linear monoethylenically unsaturated C -C 10 -C 24 fatty acids are monocarboxylic acids. Preferably, the linear monoethylenically unsaturated C 10 -C 24 fatty acids are oleic acid, gadoleic acid, erucic acid, nervonic acid, or a mixture thereof.

[0048] In certain embodiments, in a method of preparing a branched C 10 -C 24 fatty acid composition, the starting material comprises at least 70% by weight oleic acid based on the total weight of the starting material. Preferably, the starting material further comprises at least 5% by weight of linear polyethylenically unsaturated C 10 -C 24 fatty acids. The linear polyethylenically unsaturated C 10 -C 24 fatty acids are monocarboxylic acids. Preferably, the linear polyethylenically unsaturated C 10 -C 24 fatty acids are linear diethylenically unsaturated C 10 -C 24 fatty acids, particularly linoleic acid.

[0049] In particular, the starting material is a fatty acid obtained from high oleic sunflower oil. Preferably, the starting material contains at least 75% by weight, more preferably at least 80% by weight, of linear monoethylenically unsaturated C 10 -C 24 fatty acids, based on the total weight of the starting material. Preferably, the starting material contains not more than 95% by weight, more preferably not more than 90% by weight, of linear monoethylenically unsaturated C 10 -C 24 fatty acids, based on the total weight of the starting material.

[0050] The clay catalyst is preferably selected from bentonite, montmorillonite, beidellite, nontronite, saponite, hormite (attapulgite, sepiolite), or mixtures thereof. Advantageously, in the method for preparing a branched C 10 -C 24 fatty acid composition, the clay catalyst is bentonite. The content of the clay catalyst is preferably 1 to 10% by weight, more preferably 2 to 8% by weight, based on the total weight of the starting material.

[0051] The present invention also relates to a method for preparing a composition of esters of branched C 10 -C 24 fatty acids, comprising the step of esterifying a branched C 10 -C 24 fatty acid composition obtained according to the method for preparing a branched C 10 -C 24 fatty acid composition of the present invention.

[0052] In this esterification step, the branched C 10 -C 24 fatty acids react with an alcohol by any method known to those skilled in the art. The alcohol may be a monohydroxyl compound, a polyhydroxyl compound, or a mixture thereof. Linear, branched, monobranched, and multi-branched C 10 -C 24 fatty acid esters are as described above, including preferred and advantageous positions. According to the present application, a person skilled in the art can select an appropriate alcohol.

[0053] The method according to the present invention enables the obtaining of a composition of branched C 10 -C 24 fatty acids or esters thereof, wherein the weight ratio of the monobranched / multibranched of the branched C 18 fatty acids is 0.5 to 1.5, preferably 0.5 to 1.4, and more preferably 0.6 to 1.3. Advantageously, the method according to the present invention enables the obtaining of the composition according to the present invention. Thus, the composition according to the present invention is obtained by the method according to the present invention which is an economically feasible method.

[0054] Preparing a composition of branched fatty acid esters is useful because the composition can be added as a functional component in different applications such as industrial applications, personal care applications or home care applications. Thus, for these applications, especially for the applications described below, the composition according to the present invention is preferably a composition of branched C 10 -C 24 fatty acid esters, more preferably a composition of branched C 16 -C 18 fatty acid esters.

[0055] The present invention also relates to the use of the composition of the present invention in a composition of a lubricant, a personal care product, and / or a home care product.

[0056] The composition according to the present invention has many characteristics. In particular, the composition of branched C 10 -C 24 fatty acid esters according to the present invention, preferably the composition of branched C 16 -C 18 fatty acid esters exhibits excellent low-temperature stability characteristics and is thus useful in a lubricating oil composition.

[0057] Thus, the present invention also relates to a lubricating oil composition comprising the composition of the present invention and a base oil. Preferably, the content of the base oil is at least 50% by weight, more preferably at least 75% by weight, based on the weight of the lubricating oil composition.

[0058] The base oil may comprise one or more oils selected from the group consisting of mineral oils, renewable oils, and / or synthetic oils. Preferably, the base oil is selected from the group consisting of mineral oils and / or synthetic oils. Mineral oil refers to the oil obtained by petroleum refining. It is basically composed of carbon atoms and hydrogen atoms, and includes paraffin oil, hydrorefined oil, hydrocracked oil, hydroisomerized oil, etc.

[0059] Mineral oils are classified into three groups: Group I: These oils have a saturated hydrocarbon content of less than 90% by weight, an aromatic hydrocarbon content of more than 1.7% by weight, a sulfur content of more than 0.03% by weight, and a viscosity index of 80 - 120; Group II: These oils have a saturated hydrocarbon content of more than 90% by weight, an aromatic hydrocarbon content of less than 1.7% by weight, a sulfur content of less than 0.03% by weight, and a viscosity index of 80 or more and 120 or less. Group III: These oils have a saturated hydrocarbon content of more than 90% by weight, an aromatic hydrocarbon content of less than 1.7% by weight, a sulfur content of less than 0.03% by weight, and a viscosity index of more than 120; Here, the weight percentages are based on the weight of the oil.

[0060] Synthetic oils are obtained by chemical reactions between molecules derived from petrochemicals and / or renewable oils, excluding the usual chemical reactions used to obtain mineral oils (e.g., hydrorefining, hydrocracking, hydrotreatment, hydroisomerization, etc.). Examples of synthetic oils are esters, polyalkylene glycols (PAG), and polyalphaolefins (PAO). Preferably, the synthetic oil is polyalkylene glycol (PAG), polyalphaolefin (PAO), or a mixture thereof.

[0061] The lubricating oil composition of the present invention finds advantageous uses in the industrial field, automotive field, maritime field, and metalworking field.

[0062] Examples of lubricating oil compositions in the industrial field include textile fiber oils, industrial transmission oils, compressor oils, turbine oils, gear oils, hydraulic oils, and the like. Examples of lubricating oil compositions in the automotive field include hydraulic oils, transmission fluids, coolant fluids, engine oils, axle oils, gearbox fluids, brake fluids, shock absorber oils, damper oils, and the like. Examples of lubricating oil compositions in the maritime field include stern tube oils, thruster oils, and the like.

[0063] In this patent application, the terms "oil" and "fluid" are used interchangeably in the designation of the use / application of the composition according to the present invention. Examples of lubricating oil compositions in the metalworking field, also called metalworking oils or metalworking fluids, include rolling oils, cutting oils, grinding oils, quenching oils, drawing oils, press working oils, and mold oils.

[0064] Preferably, the composition according to the present invention can be used for the preparation of lubricating oil compositions for the automotive field and / or the industrial field. The composition according to the present invention, particularly the composition of branched C 10 -C 24 The composition of fatty acid esters can also be used in the method for demulsifying crude oil emulsions. In particular, the ester obtained by the method for preparing the composition of branched C 10 -C 24 The ester obtained by the method for preparing the composition of fatty acid esters of fatty acids, in which the esterification step is carried out using trimethylolpropane as the alcohol, enables faster demulsification than the corresponding esters obtained from commercially available branched fatty acids.

[0065] In the composition of cosmetics, particularly personal care products, the composition according to the present invention, particularly the branched C 10 -C 24The composition of the fatty acid ester is also useful because it exhibits very good stability, especially stability against oxidation and / or temperature. The composition according to the present invention forms a film on the skin having very good permeability. Advantageously, the branched C 10 -C 24 composition of fatty acids or esters thereof, preferably a branched C 14 -C 22 composition of fatty acid esters, more preferably a branched C 16 -C 18 composition of fatty acid esters is used as an emollient.

[0066] The present invention also relates to a composition for personal care products comprising the composition of the present invention, an active ingredient, and / or a pigment or colorant. Preferably, the active ingredient is a UV blocker, an anti-aging agent, and / or a moisturizer. Preferably, the composition for personal care products comprises a branched C 10 -C 24 fatty acid ester composition according to the present invention, more preferably a branched C 14 -C 22 fatty acid ester composition according to the present invention, even more preferably a branched C 16 -C 18 fatty acid ester composition according to the present invention. Preferably, the composition for personal care products is lipstick, lip gloss, moisturizing cream, sunscreen, or mascara.

[0067] The branched C 10 -C 24 composition of fatty acid esters according to the present invention is also useful for home care applications. Also, the composition for home care products advantageously comprises the composition according to the present invention, an active ingredient, and / or a surfactant. Preferably, the composition for home care products is a detergent.

[0068] The present invention will be described in more detail by the following examples. It should be understood that the present invention according to the claims is not limited by these examples in any way.

Example

[0069] Example 1: Method for preparing the composition according to the present invention 1.1 Isomerization of linear unsaturated fatty acids 1200 grams of the fatty acids of high oleic acid sunflower oil (containing 83% by weight of oleic acid and 7.3% by weight of linoleic acid) and 60 grams of natural bentonite clay catalyst were placed together in an autoclave. The air in the autoclave was replaced with nitrogen. While stirring, the mixture was heated to 230°C. When this reaction temperature was maintained for 3 hours, the pressure rose to 4 bar(G).

[0070] Subsequently, while removing the gas components by nitrogen replacement, the reaction mixture was cooled to 80°C. After adding 18 g of 75% by weight phosphoric acid, the temperature was raised to 130°C again and the pressure was reduced to 60 mbar. These conditions were maintained for 1 hour until all the moisture was removed from the product. Thereafter, the clay catalyst was removed from the reaction product by vacuum filtration.

[0071] 1.2 Recovery of monomer fraction The monomer fraction corresponding substantially to 56% by weight was separated from the oligomer fraction by distillation at up to 260°C under 2 mbar.

[0072] 1.3 Purification of monomer fraction 0.22% of palladium-carbon catalyst was added to the monomer, and a hydrogenation step was carried out. The product was hydrogenated at 230°C and a hydrogen pressure of 22 bar(G) for 100 minutes.

[0073] Next, in order to isolate the branched fatty acids, the product was further purified by crystallization. For this purpose, an aqueous solution containing 1.2% by weight of sodium decyl sulfate and magnesium sulfate was added to the monomer fraction, and the mixture was cooled to 9°C. The aqueous phase was removed from the branched fatty acids by centrifugation together with the crystals of mainly linear fatty acids. The branched fatty acids were washed 3 times with water and finally purified by distillation at 260°C and 2 mbar.

[0074] 1.4 Analysis of the composition according to the present invention To characterize the composition of the present invention obtained after the purification step, the carboxylic acids of the branched fatty acids were esterified with methanol. Subsequently, the sample was analyzed by gas chromatography according to ISO standard 12966-1:2014.

[0075] The obtained branched C 16 -C 18 fatty acid composition is as follows: 34.9 wt% of multi-branched C 18 acid; 40.7 wt% of mono-branched C 18 acid; 8.5 wt% of branched C 16 acid; 3.9 wt% of linear and branched C8-C 15 acid; 3.8 wt% of linear C 16 acid; 2.9 wt% of linear C 18 acid; 0.8 wt% of linear C 19 -C 22 acid; 2.2 wt% of alicyclic carboxylic acid; 1.5 wt% of aromatic; 0.4 wt% of lactone; 0.3 wt% of alkylcyclopentanone; contained.

[0076] Example 2: Pour points of the composition according to the present invention and comparative compositions 2.1 Content of different branched fatty acid compositions Composition 1a is the branched fatty acid composition prepared in Example 1; Comparative composition C1a is a commercially available branched fatty acid composition (Prisorine 3505 manufactured by Croda); Comparative composition C2a is a commercially available branched fatty acid composition (Radiacid 0907 manufactured by Oleon); The content of each composition was analyzed in the same manner as in Example 1.4, and the results are shown in Table 1 below.

[0077]

Table 1

[0078] It can be seen that the content of the cyclic compound is much lower in Composition 1a (4.4% by weight) than in Compositions C1a (10.6% by weight) and C2a (13.9% by weight). In particular, the aromatic content, especially the phenylcarboxylic acid content, was low. This low aromatic content is particularly preferred in cosmetic applications. The alicyclic carboxylic acid content was even lower in Composition 1a (2.2% by weight) than in Compositions C1a (7.5% by weight) and C2a (6.6% by weight). Since the cyclic hydrocarbons are not preferably ecotoxic and have low biodegradability, it is advantageous that the content of cyclic hydrocarbons is low (for example, the content of alicyclic compounds and aromatic compounds is low).

[0079] Also, in Comparative Compositions C1a and C2a, it can be seen that the content of multi-branched C 18 is lower than that in Composition 1a. The weight ratio of the mono-branched / multi-branched of the branched C 18 fatty acid was 1.17 in Composition 1a, while it was 1.6 in C1a and 1.7 in C2a. The analysis results further showed that the content of branched C 16 fatty acid in Composition 1a was higher than the contents in Compositions C1a and C2a.

[0080] 2.2 Esterification of Fatty Acids The Composition 1a (85.5% by weight) prepared in Example 1 was esterified with trimethylolpropane (14.5% by weight). A branched fatty acid ester composition 1e containing the same content as in Composition 1a in the form of an esterified compound of the same kind as in Composition 1a (excluding unreacted non-carboxylic acid compounds present in Composition 1a) was obtained. The ester was a mixture of monoester (2% by weight), diester (11% by weight), and triester (87% by weight) of trimethylolpropane and carboxylic acid in Composition 1a.

[0081] Further, the comparative composition C2a (85.5% by weight) was esterified with trimethylolpropane (14.5% by weight) in the same manner as in Composition 1a to produce a comparative composition C2e of a branched fatty acid ester. The obtained comparative composition C2e contained the same content as the comparative composition C2a in the form of an esterified product of the same kind of compounds as the comparative composition C2a (excluding unreacted non-carboxylic acid compounds present in Composition 1a).

[0082] 2.3 Determination of Pour Point The pour point was determined according to the method described in ASTM D97. The results obtained for each composition of the branched fatty acid ester are summarized in Table 2 below.

[0083] [Table 2]

[0084] As can be seen from this table, the composition according to the present invention, which has a lower content of cyclic compounds and a higher content of multi-branched compositions, has a lower pour point. In applications such as the lubricating oil field, the lower the pour point, the better.

Claims

1. Branch C １０ -C ２４ A composition of a fatty acid or its ester, comprising the following: At least 30% by weight of a multi-branched C １０ -C ２４ fatty acid, or an ester thereof, 1 to 8% by weight of a cyclic compound, comprising, the weight percentage being given with respect to the total weight of the composition, branched C １０ -C ２４ composition of fatty acids or esters thereof.

2. The cyclic compound contains one or more alicyclic carboxylic acids or one or more esters thereof, and the content is 0.5 to 6% by weight based on the total weight of the composition. The composition according to Claim 1.

3. At least 15% by weight, based on the total weight of the composition, of a monounsaturated C １０ -C ２４ fatty acid, or an ester thereof, the composition according to claim 1 or claim 2.

4. C １８ The composition according to any one of claims 1 to 3, wherein the weight ratio of the monobranched / multibranched form of the fatty acid or its ester is 0.5 to 1.

5.

5. At least 50% by weight, based on the total weight of the composition, of monobranched and multibranched C １０ -C ２４ The composition according to any one of claims 1 to 4, comprising a fatty acid or an ester thereof.

6. 1 to 25% by weight, based on the total weight of the composition, of one or more linear saturated C ８ -C ２４ fatty acids, or one or more esters thereof, the composition according to any one of claims 1 to 5.

7. Branched C from the starting material １０ -C ２４ A method for preparing a composition of fatty acids, wherein the starting material comprises at least 70% by weight, based on the total weight of the starting material, of one or more linear monoethylenically unsaturated C １０ -C ２４ fatty acids, and the method comprises the following: i) By heating in the presence of a clay catalyst, isomerizing the one or more linear monoethylenically unsaturated C １０ -C ２４ fatty acids; ii) A step of separating a monomer fraction from the oligomer fraction formed during step i), iii) purifying the monomer fraction to obtain the branched C １０ -C ２４ fatty acid composition; A method comprising.

8. The starting material contains at least 70% by weight of oleic acid based on the total weight of the starting material. The method according to Claim 7.

9. The starting material contains at least 5% by weight, based on the total weight of the starting material, of one or more linear polyethylene-unsaturated C １０ -C ２４ fatty acids, the method according to claim 7 or claim 8.

10. The starting material is a fatty acid obtained from high-oleic acid sunflower oil, high-oleic acid safflower oil, crambe oil, lunaria oil, or olive oil. The method according to any one of Claims 7 to 9.

11. The clay catalyst is bentonite. The method according to any one of Claims 7 to 10.

12. Branched C １０ -C ２４ A method for preparing a composition of esters of fatty acids, the branched C according to any one of claims 7 to 11 １０ -C ２４ A method for preparing a composition of fatty acids, and the branched C １０ -C ２４ A further step of esterifying the composition of fatty acids, the branched C １０ -C ２４ A method for preparing a composition of esters of fatty acids.

13. Use of the composition according to any one of Claims 1 to 6 in a composition of a lubricant, personal care product, and / or home care product.

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