Triester of cyclohexane tripropionic acid

Abstract

To provide a novel plasticizer that is extremely good in gelling ability and is excellent in high-temperature properties.SOLUTION: This invention relates to triesters of cyclohexanetripropionic acid, such as tri(n-butyl)-cyclohexane-1,2,4-tripropionate, tri(methylpropyl)-cyclohexane-1,2,4-tripropionate, tri(n-pentyl) cyclohexane-1,2,4-tripropionate, tri(iso-pentyl)-cyclohexane-1,2,4-tripropionate, tri(2-methylbutyl)-cyclohexane-1,2,4-tripropionate, and tri(3-methylbutyl)-cyclohexane-1,2,4-tripropionate, wherein three alcohol moieties of the three ester groups each contain 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to the reagent cyclohexane tripropionic acid, its preparation and use as a plasticizer for polymers. [Background technology]

[0002] To improve processability and to adapt the application-related properties to the respective requirements, polymer plasticizers are added. Plasticizers with various effect profiles are available to achieve specific desired properties. Compounds of the phthalate ester group are among the most important plasticizers for PVC and vinyl chloride-containing copolymers.

[0003] The properties of phthalate esters depend on factors including the number of carbon atoms in the alcohol portion of the ester functional group, making them more or less suitable for different plasticizer applications. Phthalate esters with short-chain alcohol moieties, such as dibutyl phthalate and dipentyl phthalate, are advantageous due to their low gelling temperature, i.e., they are used as fast-acting gelling agents, but they are highly volatile and unsuitable for other applications. Phthalate esters with long-chain alcohol moieties, such as diisononyl phthalate (DINP), actually have inferior gelling properties compared to their lighter congeners. While they also benefit from their low volatility, their volatility is still too high for certain high-temperature applications. While di(tri)decyl phthalate has relatively low volatility, this phthalate is not sufficient for many high-temperature applications. Phthalates with more than 13 carbon atoms in the alcohol moiety have poor polymer compatibility and the corresponding polymer-phthalate mixtures tend to segregate, so none of the phthalic acid plasticizers with more than 13 carbon atoms in the alcohol moiety are used as plasticizers, for example, in high-temperature cables.

[0004] Due to their lower volatility compared to phthalate esters, the trimellitate family of plasticizers is used in high-temperature applications. The textbook, "Ethylene Propylene Glycol Trimellitate (EPO)," describes trimellitate esters with alcohol moieties containing 7 to 9 carbon atoms or C6- and C8-esters or mixtures of C7-, C8-, and C9-esters of trimellitic acid for commercial use, highlighting tri(2-ethylhexyl)trimellitate as the most important trimellitate ester. However, even these trimellitate esters are often too volatile for use in high-temperature cables.

[0005] US Pat. No. 5,629,493 discloses trimellitic esters and cyclohexane-1,2,4-tricarboxylic acid and their suitability as plasticizers. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] U.S. Patent Application Publication No. 2018 / 0319954 [Non-patent literature]

[0007] [Non-Patent Document 1] “Plasticizers ― Principles and Practice” AS Wilson (The Institute of Materials, 1995, pages 166 to 170) Summary of the Invention [Problem to be solved by the invention]

[0008] The object of the present invention is to provide a new class of plasticizers that generally have a wide range of properties, i.e., can be used in many different applications. The new class of plasticizers may preferably include agents with very good gelling ability and agents with excellent high temperature properties. Typically, the new class of plasticizers may preferably be superior to trimellitic esters in high temperature applications such as cables. [Means for solving the problem]

[0009] This object is achieved by a triester of cyclohexane tripropionic acid according to claim 1. The invention relates to triesters of cyclohexane tripropionic acid, in which the three alcohol moieties of the three ester groups each contain 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.

[0010] As with all carboxylic acid esters, the triesters of cyclohexane trippropionic acid are formally formed from a carboxylic acid and an alcohol, thereby containing an acid moiety and an alcohol moiety. The triesters of cyclohexane trippropionic acid of the present invention are composed of a cyclohexane trippropionic acid moiety and three alcohol moieties, each of which contains 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.

[0011] The triesters of cyclohexane tripropionic acid of the present invention are also referred to hereinafter by the abbreviated name triesters of the present invention.

[0012] Surprisingly, it has been found that representatives of this new plasticizer group are suitable for plastisol applications, have low gelling temperatures, and can be advantageously used as fast-acting gelling agents, while other representatives of this group can be advantageously used in thermoplastic applications. In plastisol and thermoplastic applications, representatives of this plasticizer group exhibit low mass loss. Good low-temperature flexibility (low glass transition temperature) can be achieved with representatives of this group.

[0013] In addition to the desired suitability of representatives of the new plasticizer family for high temperature applications, representatives of this family allow for low viscosities in plastisol applications, along with advantageous thickening properties of the plastisol in question.

[0014] The three propionic ester groups of the ester of the invention can be attached to various positions on the cyclohexane ring, however the triester according to the invention is preferably a triester of cyclohexane-1,2,4-tripropionic acid or a triester of cyclohexane-1,3,5-tripropionic acid, in particular a triester of cyclohexane-1,2,4-tripropionic acid.

[0015] The alcohol moiety of the triester of cyclohexane tripropionic acid can be a cyclic or acyclic alkyl group with or without a functional group containing a multiple bond, regardless of whether the functional group originates from the alcohol used to prepare the triester of the invention or is subsequently inserted into the triester molecule. Similarly, alcohol moieties containing an aromatic ring with no functional group or one or more functional groups are also possible. The alcohol moiety of the triester of the invention preferably contains no other heteroatoms and no multiple bonds, apart from the oxygen atom of the ester functional group. The alcohol moiety is formally based on an alkanol, preferably an acyclic alkanol, which has the advantage that the preparation of the resulting triester is particularly inexpensive due to the ready availability of alkanols.

[0016] The present invention relates to triesters of cyclohexane tripropionic acid, preferably in which the three alcohol moieties of the three ester groups each contain 2 to 9, preferably 4 to 9, 5, 6, 7, 8, or 9 carbon atoms. These reagents are characterized by good gelling properties and low plastisol viscosities, with the viscosity of plastisols prepared therewith increasing only slightly over time. In plastisols, e.g., film applications, mass loss in air is negligible. The low-temperature flexibility of test specimens containing these triesters is higher than that of comparative compounds, as evidenced by their low glass transition temperatures. However, the triesters according to the present invention are preferably triesters of cyclohexane-1,2,4-tripropionic acid or cyclohexane-1,3,5-tripropionic acid, particularly triesters of cyclohexane-1,2,4-tripropionic acid, in which the alcohol moieties are preferably derived morphologically from an acyclic alkanol.

[0017] The present invention also relates to a triester of cyclohexane tripropionic acid, in which the three alcohol moieties of the three ester groups each contain 7 to 12, preferably 8 to 10, and especially 8 or 9 carbon atoms. The triester is characterized by very low mass loss at high temperatures, making it highly suitable for high-temperature applications. Furthermore, the low-temperature flexibility of test specimens containing the triester is higher than that of comparative compounds. However, the triester according to the present invention is preferably a triester of cyclohexane-1,2,4-tripropionic acid or a triester of cyclohexane-1,3,5-tripropionic acid, in particular a triester of cyclohexane-1,2,4-tripropionic acid, in which the alcohol moiety is preferably derived formally from an acyclic alkanol.

[0018] The triesters of the present invention preferably contain the same aryl group in one molecule. molecule In this case, the "identical" alcohol moieties in one triester are moleculeThe alcohol moieties of formula "" may have the same arrangement of atoms present or may differ in structure, i.e., be isomeric alcohol moieties. Preferably, all alcohol moieties present in one molecule of the triester of the present invention are molecule The formula is the same and at the same time the structural formula is the same or different. molecule The triesters of the present invention, which have the same formula but different structural formulas, contain isomeric alcohol groups and are also advantageously liquid at low temperatures.

[0019] The triesters of the present invention preferably contain the same aryl group in one molecule. molecule In this case, the "identical" alcohol moieties in one triester are molecule The alcohol moieties of formula "" may have the same arrangement of atoms present or may differ in structure, i.e., be isomeric alcohol moieties. Preferably, all alcohol moieties present in one molecule of the triester of the present invention are molecule The formula is the same and at the same time the structural formula is the same or different. molecule The triesters of the present invention, which have the same formula but different structural formulas, contain isomeric alcohol groups and are also advantageously liquid at low temperatures. Preferred triesters of cyclohexane tripropionic acid, i.e., triesters of cyclohexane-1,2,4-tripropionic acid, include those of Formula I: [ka] where the R group is: molecule The formula is the same and at the same time the structural formula may be the same or different.

[0020] [ka] where the R groups have the same empirical formula and at the same time the structural formula may be the same or different.

[0021] In one embodiment, the R group of formula I is an acyclic alkyl group having from 2 to 8 or 9 carbon atoms, particularly 4, 5, 6 or 7. In another embodiment, the R group of formula I is an acyclic alkyl group having from 7 to 10 carbon atoms, particularly 8 or 9 carbon atoms.

[0022] The present invention further relates to a mixture of at least two triesters of cyclohexane tripropionic acid according to the invention, wherein the at least two triesters according to the invention are molecule The formula, its structural formula, or both may differ. molecule Examples of mixtures of different formulas, which mixtures comprise at least two triesters according to the invention, are tri( n A mixture of cyclohexane-1,2,4-tripropionic acid and tri(2-ethylhexyl)cyclohexane-1,2,4-tripropionic acid is also known. When at least two esters of the present invention differ in their structural formula, at least one triester of cyclohexane-1,2,4-tripropionic acid and at least one triester of cyclohexane-1,3,5-tripropionic acid may be present in the mixture. Alternatively, or in addition to possible differences in the position of the propionic ester group on the cyclohexane ring, the mixture may contain "identical" esters of different structures. molecule The mixture may comprise at least two triesters according to the invention containing alcohol moieties of the formula ", i.e., isomeric alcohol moieties. For example, the mixture may comprise one triester according to the invention in which the alcohol moiety is always linear and one in which the alcohol moiety is uniformly branched. An example of such a mixture is a mixture of tri( n It is a combination of tri(pentyl)cyclohexane-1,2,4-tripropionic acid and tri(2-methylbutyl)cyclohexane-1,2,4-tripropionic acid. n butyl)cyclohexane-1,2,4-tripropionic acid, tri( iso Pentyl)cyclohexane-1,2,4-tripropionic acid, tri( n butyl)cyclohexane-1,3,5-tripropionic acid and tri( isoIt may also be a more complex mixture containing pentyl)cyclohexane-1,3,5-tripropionic acid.

[0023] The prefix "iso" denotes the fact that it is a mixture of isomers with a common carbon number. iso The pentyl group contains at least two isomeric alkyl groups with five carbon atoms, and this method does not provide information on the number of isomers or the ratio of which isomers are present. iso In the case where the tri-ester is not present exclusively in an isomeric mixture of alkyl)cyclohexane tripropionates, that is, it is a mixture of at least two triesters according to the present invention which have different structural formulas.

[0024] Preferred triesters according to the invention or mixtures according to the invention are: Bird ( n butyl)cyclohexane-1,2,4-tripropionic acid, tri(methylpropyl)cyclohexane-1,2,4-tripropionic acid, tri( n Pentyl)cyclohexane-1,2,4-tripropionic acid, tri( iso pentyl)cyclohexane-1,2,4-tripropionic acid, tri(2-methylbutyl)cyclohexane-1,2,4-tripropionic acid, tri(3-methylbutyl)cyclohexane-1,2,4-tripropionic acid, tri( n hexyl)cyclohexane-1,2,4-tripropionic acid, tri( iso hexyl)cyclohexane-1,2,4-tripropionic acid, tri( n Heptyl)cyclohexane-1,2,4-tripropionic acid. Tri( iso Heptyl)cyclohexane-1,2,4-tripropionic acid, tri( n Octyl)cyclohexane-1,2,4-tripropionic acid, tri( iso Octyl)cyclohexane-1,2,4-tripropionic acid, tri(2-ethylhexyl)cyclohexane-1,2,4-tripropionic acid, tri( nNonyl)cyclohexane-1,2,4-tripropionic acid, tri( iso Nonyl)cyclohexane-1,2,4-tripropionic acid, tri( n decyl)cyclohexane-1,2,4-tripropionic acid, tri( iso Decyl)cyclohexane-1,2,4-tripropionic acid, tri(2-propylheptyl)cyclohexane-1,2,4-tripropionic acid; Tri(n-butyl)cyclohexane-1,3,5-tripropionic acid, Tri(methylpropyl)cyclohexane-1,3,5-tripropionic acid, Tri( n Pentyl)cyclohexane-1,3,5-tripropionic acid, tri( iso pentyl)cyclohexane-1,3,5-tripropionic acid, tri(2-methylbutyl)cyclohexane-1,3,5-tripropionic acid, tri(3-methylbutyl)cyclohexane-1,3,5-tripropionic acid, tri( n hexyl)cyclohexane-1,3,5-tripropionic acid, tri( iso hexyl)cyclohexane-1,3,5-tripropionic acid, tri( n heptyl)cyclohexane-1,3,5-tripropionic acid, tri( iso Heptyl)cyclohexane-1,3,5-tripropionic acid, tri( n Octyl)cyclohexane-1,3,5-tripropionic acid, tri( iso Octyl)cyclohexane-1,3,5-tripropionic acid, tri(2-ethylhexyl)cyclohexane-1,3,5-tripropionic acid, tri( n Nonyl)cyclohexane-1,3,5-tripropionic acid, tri( iso Nonyl)cyclohexane-1,3,5-tripropionic acid, tri( n decyl)cyclohexane-1,3,5-tripropionic acid, tri( iso decyl)cyclohexane-1,3,5-tripropionic acid, and tri(2-propylheptyl)cyclohexane-1,3,5-tripropionic acid.

[0025] As mentioned above, the esters of the present invention have advantageous properties when used as plasticizers for polymers. The present invention further relates to plasticizers for polymers, which comprise the triesters of the present invention or the mixtures of the present invention (comprising at least two of the triesters), and optionally at least one additional polymer-plasticizing compound. These plasticizers are particularly suitable for PVC.

[0026] The present invention also relates to a composition comprising a triester according to the invention or a mixture according to the invention (comprising at least two of said triesters) or a plasticizer according to the invention and one or more polymers.

[0027] Suitable polymers are preferably polyvinyl chloride (PVC), ethylene, propylene, butadiene, vinyl acetate, glycidyl acrylate, glycidyl methacrylate, ethyl acrylate, butyl acrylate or methacrylate with alkoxy groups of branched or unbranched alcohols having 1 to 10 carbon atoms, homo- or copolymers based on acrylonitrile or cyclic olefins, polyvinylidene chloride (PVDC), polyacrylates, in particular polymethyl methacrylate (PMMA), polyalkyl methacrylates (PAMA), polyurea, silylated polymers, fluoropolymers, in particular polyvinylfluoride. polyvinyl acetal (PVDF), polytetrafluoroethylene (PTFE), polyvinyl acetate (PVAc), polyvinyl alcohol (PVA), polyvinyl acetal, in particular polyvinyl butyral (PVB), polystyrene polymers, in particular polystyrene (PS), expandable polystyrene (EPS), acrylonitrile-acrylic (ASA), styrene-acrylonitrile-butadiene-styrene (ABS), styrene-maleic anhydride (SMA), styrene-methacrylic acid copolymer, polyolefins, in particular polyethylene (PE) or polypropylene (PP), thermoplastic polyolefins (TPO), polyethylene The polymer may be selected from the group consisting of vinyl acetate (EVA), polycarbonate, polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyoxymethylene (POM), polyamide (PA), polyethylene glycol (PEG), polyurethane (PU), thermoplastic polyurethane (TPU), polysulfide (PSu), biopolymers, in particular polylactic acid (PLA), polyhydroxybutyral (PHB), polyhydroxyvaleric acid (PHV), polyester, starch, cellulose and cellulose derivatives, in particular nitrocellulose (NC), ethylcellulose (EC), cellulose acetate (CA), cellulose acetate / butyrate (CAB), rubber and silicone.

[0028] In a preferred embodiment, at least one polymer in the composition, preferably at least 90% by weight of said polymer, is selected from the group consisting of polyvinyl chloride (PVC), polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfide, polylactic acid (PLA), polyhydroxybutyral (PHB), nitrocellulose, and copolymers of vinyl chloride with vinyl acetate or butyl acrylate.

[0029] The amount of triester in the composition according to the invention comprising one or more polymers is preferably from 5 to 150 parts by weight, preferably from 10 to 120 parts by weight, particularly preferably from 15 to 110 parts by weight, and particularly preferably from 20 to 100 parts by weight per 100 parts by weight of polymer. However, it is also conceivable that the composition comprising one or more polymers comprises less than 20 parts by weight of triester according to the invention per 100 parts by weight of polymer.

[0030] The compositions of the present invention are preferably adhesives, sealants, coatings, lacquers, paints, plastisols, dry blends, foams, synthetic leather, flooring, especially the top layer or foam layer thereof, roofing membranes, soffit protection, textile coatings, cables, wire insulation, hoses, extruded articles, films, automotive interior articles, wallpaper, inks, toys, contact sheets, food packaging or medical articles, especially tubing protection or a component of blood bags.

[0031] The present invention further relates to the use of the triesters according to the invention or the mixtures according to the invention (comprising at least two of the triesters) as plasticizers for polymers. The triesters according to the invention or the mixtures according to the invention (comprising at least two of the triesters) are preferably used as plasticizers for the above polymers, in particular polyvinyl chloride (PVC), polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfide, polylactic acid (PLA), polyhydroxybutyral (PHB), nitrocellulose, and copolymers of vinyl chloride with vinyl acetate or butyl acrylate. Their use as plasticizers for polyvinyl chloride (PVC) is particularly preferred.

[0032] The use is therefore preferably the use of the triesters of the invention or the mixtures of the invention (comprising at least two of the triesters) in adhesives, sealants, coatings, lacquers, paints, plastisols, dry blends, foams, synthetic leather, flooring, in particular the top layer or foam layer thereof, roofing membranes, underside protection, textile coatings, cables, wire insulation, hoses, extruded articles, films, articles for automotive interiors, wallpaper, inks, toys, contact sheets, food packaging or medical articles, in particular the protection of tubes or blood bags.

[0033] In a preferred embodiment, triesters of cyclohexane tripropionic acid, in which the three alcohol moieties of the three ester groups contain 7 to 12 carbon atoms, preferably 8 to 10, especially 8 or 9 carbon atoms, are used as polymer plasticizing compounds for high temperature applications, especially for high temperature cable or dashboard components.

[0034] In another preferred embodiment, triesters of cyclohexane tripropionic acid, in which the three alcohol moieties of the three ester groups contain 2 to 9 carbon atoms, preferably 4 to 9, 5, 6, 7, 8 or 9 carbon atoms, are used as polymer plasticizing compounds for plastisol applications, preferably textile coatings, wallpaper, synthetic leather, films, roofing membranes and floor coverings.

[0035] The triesters of the present invention are as follows: -Ring hydrogenation of the corresponding triester of benzenetrippropionic acid; - transesterification of a trialkyl ester of cyclohexane tripropic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, wherein the alcohol of the alcohol moiety of the incorporated trialkyl ester has a higher boiling point than the alcohol of the alcohol moiety that is replaced in the context of the transesterification; - esterification of cyclohexane tripropionic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - alkoxycarbonylation of trivinylcyclohexane with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; It can be prepared by a method comprising:

[0036] Preferably, the trimethyl ester or triethyl ester is used in the transesterification reaction.

[0037] The present disclosure preferably comprises the following: - ring hydrogenation of triesters of benzenetriprionic acid, the alcohol moieties of the ester groups each containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - transesterification of a trialkyl ester of cyclohexane tripropropionic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, wherein the alcohol of the alcohol moiety of the incorporated trialkyl ester has a higher boiling point than the alcohol of the alcohol moiety that is replaced in the context of the transesterification; - esterification of cyclohexane tripropionic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - alkoxycarbonylation of trivinylcyclohexane with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; Preparation of triesters of cyclohexane tripropionic acid according to the invention by

[0038] For the preparation of triesters of cyclohexane-1,2,4-tripropionic acid, it is particularly preferred to use the respective cyclohexane-1,2,4 compound.

[0039] Preferably, the trimethyl ester or triethyl ester is used in the transesterification reaction.

[0040] The present invention particularly preferably comprises the following: - ring hydrogenation of triesters of benzene-1,2,4-tripropionic acid, the alcohol moieties of the ester groups each containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - transesterification of the trimethyl ester or the triethyl ester of cyclohexane-1,2,4-tripropionic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - esterification of cyclohexane-1,2,4-tripropionic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - alkoxycarbonylation of 1,2,4-trivinylcyclohexane with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; The present invention relates to the preparation of triesters of cyclohexane-1,2,4-tripropionic acid according to the method of the present invention.

[0041] The triester of benzene-1,2,4-tripropionic acid can be obtained by ring hydrogenation of the triester in one or more hydrogenation units connected in series. The hydrogenation units preferably each comprise at least one, preferably two or more, hydrogenation reactors. The at least one hydrogenation reactor may be a tubular reactor, a tube bundle reactor, or preferably a shaft oven. The individual reactors can be operated adiabatically, polytropically, or substantially isothermally, i.e., with a temperature rise of typically less than 10°C. In this case, reactors operating in loop mode are particularly driven quasi-isothermally, preferably with a temperature rise of less than 10°C, particularly preferably less than 5°C. One or more hydrogenation units can be operated in loop mode.

[0042] The hydrogenation of the triester of benzene trippropionic acid is preferably carried out continuously using a hydrogen-containing gas over a solid catalyst arranged in a fixed bed.

[0043] The hydrogenation gas used can be any hydrogen-containing gas mixture that does not contain harmful amounts of catalyst poisons such as carbon monoxide or hydrogen sulfide. Optionally, an inert gas may be used, preferably with hydrogen purity above 95%, particularly above 98%. The inert gas fraction can be, for example, nitrogen or methane.

[0044] Preferably, the solid hydrogenation catalyst contains at least one metal from transition group 8 of the periodic table of the elements. The active metal from transition group 8 of the periodic table of the elements used is preferably platinum, rhodium, palladium, cobalt, nickel, or ruthenium, or a mixture of two or more thereof, with ruthenium being particularly preferred as the active metal. In addition to the above metals, at least one metal from transition groups 1 and / or 7 of the periodic table of the elements may also be present in the catalyst. Preferably, rhenium and / or copper are used. The catalyst used is preferably a supported catalyst. Examples of supports that can be used include activated carbon, silicon carbide, aluminum oxide, silicon oxide, aluminum silicate, titanium dioxide, zirconium dioxide, magnesium oxide, and / or zinc oxide, or mixtures thereof. It is particularly preferred to use a catalyst with an aluminum oxide or titanium dioxide support. Furthermore, the support material may contain an alkali metal, an alkaline earth metal, and / or sulfur. Preferably, a ruthenium catalyst is used.

[0045] The hydrogenation process is preferably carried out in a liquid / gas mixed phase in a three-phase reactor or in co-flow in the liquid phase, with the hydrogenation gas being distributed in the liquid reactant / product stream in a manner known per se. Due to the homogeneous liquid distribution, improved removal of the heat of reaction and / or high space-time yields, reactors operating in loop mode are preferably used with a cross section of 1 m of the empty reactor. 2 10 to 400, preferably 20 to 200, particularly preferably 40 to 150 m per hour 3 It is preferable to operate at a high liquid load of .

[0046] The hydrogenation can be carried out in the absence of a solvent, or preferably in the presence of a solvent. The solvent used can be any liquid that forms a homogeneous solution with the reactants and product, is inert under hydrogenation conditions, and can be easily removed from the product. The solvent can also be a mixture of two or more substances, and in some cases, contains water. Most preferably, the product of the hydrogenation is used as the solvent.

[0047] The transesterification of the trimethyl ester of cyclohexane trippropionic acid with at least one alcohol containing 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms and the esterification of cyclohexane trippropionic acid with one or more of these alcohols are preferably carried out in the presence of one or more catalysts, for example, using a Brønsted acid or base or a Lewis acid or base as catalyst. Particularly suitable catalysts have been found to be sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, metals, or compounds thereof. Particularly preferred metal catalysts include tin powder, tin(II) oxide, tin(II) oxalate, titanate esters such as tetraisopropyl orthotitanate or tetrabutyl orthotitanate, and zirconium esters such as tetrabutylzirconate, as well as sodium methoxide and potassium methoxide. Cyclohexane trippropionic acid can be obtained by hydroxycarbonylation, i.e., the noble metal-catalyzed reaction of trivinylcyclohexane with CO and HO.

[0048] The esterification and transesterification processes can be carried out in conventional esterification equipment known to those skilled in the art under conventional process conditions. The processes are preferably carried out at a temperature above the boiling point of the alcohol formed during the reaction so that it can be distilled off from the reaction mixture. Examples of suitable transesterification reactions are described in the experimental section.

[0049] The esterification or transesterification process is preferably carried out at 100 to 300° C., preferably 120 to 270° C., in particular 140 to 250° C. The pressure in the esterification apparatus is preferably 0.1 to 20 bar or 15 bar, in particular 0.1 to 10 bar.

[0050] The alkoxycarbonylation process is preferably the following: a) the following compounds (i), (ii), and (iii):

[0051] [ka] a step of initially charging one of said compounds or a mixture of at least two of said compounds; b) The following ligand (L):

[0052] [ka] and adding a compound containing Pd or a complex containing Pd and a ligand (L); c) adding an alcohol having 1 to 12 carbon atoms; d) CO supply step; e) heating the reaction mixture of steps a)-d) to convert the compound / mixture of a) into a triester; The process includes:

[0053] In one variation of the method, compound (i) is initially charged in process step a), and in another variation, compound (ii) is initially charged. The alcohol of step (c) preferably does not contain any heteroatoms other than oxygen, does not contain any multiple bonds, and is in particular methanol, ethanol, n Butanol, methylpropanol, n pentanol, iso Pentanol, 2-methylbutanol, 3-methylbutanol, n hexanol, iso hexanol, n Heptanol,iso Heptanol, n Octanol, iso Octanol, 2-ethylhexanol, n Nonanol, iso Nonanol, n Decanol, iso It is selected from decanol and 2-propylheptanol.

[0054] Particularly preferred is the preparation of the trimethyl ester by methoxycarbonylation, which is then transesterified to give the triester or a mixture of triesters according to the invention.

[0055] In the alkoxycarbonylation, CO is added in step d) to a pressure preferably in the range of 20 bar to 60 bar, particularly 30 bar to 50 bar. The temperature in step (e) is preferably in the range of 90°C to 130°C, particularly 100°C to 120°C.

[0056] After the alkoxycarbonylation, the triester is preferably purified in step f). [Example]

[0057] Acid Number: The acid number was determined in accordance with DIN EN ISO 2114. GC analysis: GC analysis was performed using the following parameters: Capillary column: 30m DB5, 0.25mm ID, 0.25µm film Carrier gas: Helium Column pressure: Split: Approx. 23.8 ml / min Furnace temperature program (duration: 50°C (1 minute), 7.5°C / min to 350°C (30 minute hold)) Injector: 350℃ Detector (FID): 400℃ Injection volume: 1.0 μl Components in the sample chromatograms were identified using reference solutions of the relevant esters. The signals in the sample chromatograms were then normalized to 100%. The molar ratios were determined to a good approximation from the area ratios of the individual signals. Purity was measured via the fraction of the product signal as a percentage of the total area in the chromatogram. Example 0: Synthesis of trimethylcyclohexane-1,2,4-tripropionic acid

[0058] [ka] [Pd(acac)2] (15.2 mg, 0.1 mol%), (L) (previous formula, 103 mg, 0.4 mol%), and paratoluenesulfonic acid (PTSA, 143 mg, 1.5 mol%) were placed in a 100 ml steel autoclave under an argon atmosphere. Methanol (MeOH, 30 ml) and trivinylcyclohexane (i) (8.1 g, 50 mmol) were then injected via syringe. The autoclave was flushed with CO three times and then pressurized with 40 bar of CO pressure. The reaction was carried out at 110 °C for 10 h. The autoclave was then cooled to room temperature and depressurized. The desired product was obtained by distillation (10 -3 The product was purified by NMR spectroscopy (at 165°C at bar) and characterized by 1H-, 13C-NMR and HR-MS (15.6 g, yield 91%, purity 98%).

[0059] [ka] Examples 1 to 5: Preparation of trialkylcyclohexane-1,2,4-tripropionic acids according to the present invention In a distillation apparatus containing a Raschig ring column fitted with a dip tube, thermometer, and condenser, an initial charge of the amount of trimethylcyclohexane-1,2,4-tripropionic acid is added, and the amount of alcohol m a The apparatus was purged with nitrogen (6 L / h) through the dip tube for at least 1 hour and 0.15% by weight of tetra- nButyl butyl titanate (Sigma Aldrich, purity >97%) was added based on the mass of tripropionate. Nitrogen (6 L / h) was continued to be sparged until the end of the reaction, and the mixture was slowly heated to boiling while stirring. Methanol was produced from the reaction via a distillation head and continuously removed until the maximum temperature reached 61-63°C. If the maximum temperature exceeded 68°C, no distillate was removed. During the transesterification reaction, the amount of methanol m m was produced (reaction time t). During the reaction, samples were taken every hour and analyzed by gas chromatography. When GC analysis showed less than 0.5 area % of the monomethyl ester, the heating medium was removed and the contents of the reaction flask were cooled to 80°C while introducing nitrogen.

[0060] For processing, the crude product was transferred to a distillation apparatus equipped with a Claisen adapter and a vacuum divider. Excess alcohol was distilled off under reduced pressure (approximately 1 mbar) at a bottom temperature of approximately 160°C to approximately 180°C (tributyl and tripentyl esters approximately 160°C, tri(2-ethylhexyl) ester and tri(isononyl) ester approximately 180°C), and the mixture was cooled again under a nitrogen atmosphere. After measuring the acid value of the flask contents, the contents were stirred with three volumes of base (10% aqueous NaOH, Merck NaOH, purity >99%) at 80°C for 15 minutes with a nitrogen sparge (6 L / h). This was then filled with 2% by weight of activated carbon (Cabot Norit Nederland BV, CAP Super), based on the weight of the flask contents, and stirred for 5 minutes. The remaining volatile fractions were again removed via a nitrogen inlet under vacuum at approximately 160°C or approximately 180°C (see above), with the nitrogen flow adjusted so that the pressure did not exceed 20 mbar. When the residual alcohol content by GC analysis was less than 0.025 area %, the resulting crude product was cooled and filtered under reduced pressure through a Buchner funnel containing filter paper and a pre-compressed filter cake of filter aid (Perlite type D14) into a suction bottle.

[0061] Amount of trialkylcyclohexane-1,2,4-tripropionic acid (Tc ester) m p Each was obtained with the purity (%) specified in Table 1.

[0062] Specific characteristics of each compound: In the preparation of the tri(2-ethylhexyl), tri(isononyl), and tri(2-propylheptyl) esters, reduced pressure was applied stepwise during the transesterification process while maintaining reflux (at 240 °C), where the head temperature decreased slowly as the pressure decreased. Table 1: Details of the preparation of trialkylcyclohexane-1,2,4-tripropionic acids according to the present invention

[0063] [Table 1] * Inventive n-Butanol: Sigma-Aldrich, purity >99.4% Isopentanol: a 1:1 molar mixture of n pentanols (Sigma-Aldrich, purity >99%) and 2-methylbutanol (Sigma-Aldrich, purity >99%) 2-Ethylhexanol: Sigma-Aldrich, purity >99% Evonik Performance Materials GmbH, purity >99% Evonik Performance Materials GmbH, purity >99.5% Examples 6-10: Preparation of non-inventive trialkylcyclohexane-1,2,4-tricarboxylic acids In a distillation apparatus equipped with a condenser fitted with a submerged tube, a thermometer, and a water separator, a milliliter of cyclohexane-1,2,4-tricarboxylic acid (Ct acid, >97%) is initially charged, and an alcohol amount m aThe mixture was suspended in cyclohexane-1,2,4-tricarboxylic acid. The apparatus was purged with nitrogen (6 L / h) through the dip tube for at least 1 hour, and 0.15% by weight of tetra-n-butylbutyl titanate (Sigma Aldrich, purity >97%) was added based on the mass of cyclohexane-1,2,4-tricarboxylic acid. Nitrogen (6 L / h) was continued to be sparged until the end of the reaction, and the mixture was slowly heated to boiling while stirring. The resulting reaction water was continuously removed from the reaction via a water separator. In the absence of continuous reflux, cyclohexane m was used as an azeotropic agent. c During the esterification process, the amount of water (m w ) was produced (reaction time t). After the theoretical volume of reaction water was reached, samples were taken every 30 minutes to measure the acid value. When an acid value of <0.1 mg KOH / g was measured, the contents of the reaction flask were cooled to 80°C by removing the heat source and introducing nitrogen.

[0064] For processing, the crude product was transferred to a distillation apparatus containing a Claisen adapter with a vacuum divider. The distillation was carried out under reduced pressure (about 1 mbar) at a bottom temperature of about 160°C to about 180°C (tri( n The excess alcohol was distilled off at approximately 160°C (tri(2-ethylhexyl) ester and tri(isopentyl) ester, approximately 160°C (tri(2-ethylhexyl) ester, tri(isononyl) ester, and tri(2-propylheptyl) ester), and the mixture was cooled again under a nitrogen atmosphere. After measuring the acid value of the contents of the flask, the contents were stirred with three volumes of base (10% aqueous NaOH, Merck NaOH, purity >99%) at 80°C for 15 minutes with a nitrogen sparge (6 L / h). Then, the contents were filled with 2% by weight of activated carbon (Cabot Norit Nederland BV, CAP Super), based on the weight of the flask contents, and stirred for 5 minutes. The remaining volatile fractions were again removed under vacuum at approximately 160°C or approximately 180°C (see above) via a nitrogen inlet, and the nitrogen flow was adjusted so that the pressure did not exceed 20 mbar. When the residual alcohol content by GC analysis was less than 0.025 area %, the resulting crude product was cooled and filtered under reduced pressure through a Buchner funnel containing filter paper and a pre-compressed filter cake of filter aid (Perlite type D14) into a suction bottle.

[0065] The amounts of trialkylcyclohexane-1,2,4-tricarboxylic acids mp were each obtained with the purities (%) shown in Table 2.

[0066] Specific characteristics of each compound: Bird ( n Preparation of tetra-butyl ester: In this experiment, 0.15% by weight of sulfuric acid (Sigma-Aldrich, purity 95-97%) was added based on the weight of cyclohexane-1,2,4-tricarboxylic acid. n Additionally, when an acid number of less than 1 mg KOH / g (but not less than 0.1 mg KOH / g) was measured, nitrogen was introduced and the contents of the reaction flask were cooled to 80°C. Bird ( n butyl) ester and tri( iso Preparation of tetra-pentyl ester: n Only half the amount of butyl titanate and each alcohol was added initially, and the remaining amounts were added only when the bottom temperature reached 240°C. Table 2: Details of the preparation of non-inventive trialkylcyclohexane-1,2,4-tricarboxylic acid esters (Ct-Esters)

[0067] [Table 2] n-Butanol: Sigma-Aldrich, purity >99.4% Isopentanol: a 1:1 molar mixture of n-pentanol (Sigma-Aldrich, purity >99%) and 2-methylbutanol (Sigma-Aldrich, purity >99%) 2-Ethylhexanol: Sigma-Aldrich, purity >99% iso Nonanol: Evonik Performance Materials GmbH, purity >99% 2-Propylheptanol: Evonik Performance Materials GmbH, purity >99.5 Example 11: Intrinsic viscosity of esters of Examples 1 to 10 The viscosity was determined using a Stabinger viscometer (SVM3000 manufactured by Anton Paar), a modified version of the classic Couette rotational viscometer. The esters were injected individually and bubble-free at 20°C according to the manufacturer's instructions. The intrinsic viscosities of the esters are shown in Table 3. Table 3: Intrinsic viscosity [mPa·s] of the esters of Examples 1 to 10 at 20°C

[0068] [Table 3] Example 12: Preparation of plastisol PVC plastisols were prepared, for example, for the preparation of topcoat films for floor coverings. The values ​​in the plastisol formulations are all in units of mass. The formulations of the polymer compositions are listed in Table 4. Table 4: Plastisol formulations

[0069] [Table 4] The liquid components were first weighed and then the powder components were weighed and placed in a PE beaker. The mixture was manually stirred with an ointment spatula until no unwetted powder was present. The mixing beaker was then attached to the clamping device of a dissolver stirrer. After the stirrer was switched on, the speed was slowly increased to approximately 2000 rpm (revolutions per minute). Meanwhile, the plastisol was carefully degassed, maintaining the pressure below 20 mbar. As soon as the plastisol reached a temperature of approximately 30°C, the speed was reduced to approximately 350 rpm. The plastisol was then degassed at this speed for 9 minutes, reducing the pressure to below 20 mbar. This allowed the plastisol to be homogenized with constant energy input, after which it was immediately equilibrated to 25.0°C in a climate-controlled cabinet for further study.

[0070] Example 13: Measurement of thickening behavior The viscosity of the plastisol prepared in Example 12 was measured on a Physica MCR101 rheometer (Anton Paar Germany GmbH) using rotational mode and a CC27 measurement system with associated software. During the measurements, the following points were controlled:

[0071] -100s -1 preshearing at 40°C for 60 seconds (no measurements were taken during this time); -Shear rate 200s -1 to 0.1 seconds -1 The downward progression of the test was measured at 30 points over 10 seconds. Measurements were taken after 2 hours, 24 hours and 7 days of storage. The plastisols were stored at 25°C between measurements. The thickening behavior of the plastisol was evaluated based on the viscosity value after 2 hours, and the viscosity increase rate after 24 hours and 7 days was calculated using the values ​​of 1, 10 and 100 s -1 The measurement was carried out at a shear rate of . Table 5: 1s of the plastisol of Example 12 -1 Thickening behavior in

[0072] [Table 5] *According to the present invention Table 6: 10s of Plastisol from Example 12 -1 Thickening behavior in

[0073] [Table 6] *According to the present invention Table 7: 100s of Plastisol from Example 12-1 Thickening behavior in

[0074] [Table 7] *According to the present invention The plastisol viscosity of the trialkylcyclohexane-1,2,4-tripropionic acid of the present invention is lower than that of the comparative ester. Furthermore, the increase in viscosity of the trialkylcyclohexane-1,2,4-tripropionic acid over time is less pronounced than that of the comparative ester. Due to these advantageous properties, the triesters of the present invention can be used even after prolonged storage without the addition of viscosity-reducing additives, thereby saving the use of such additives and the time and labor associated with their use.

[0075] Example 14: Preparation of film The plastisols prepared in Example 12 were each processed to give films having a thickness of 1 mm.

[0076] For this purpose, a high-gloss release paper (Sappi, Italy) was first trimmed to a size of 30 x 44 cm and inserted into the clamp frame of an LTSV coating machine for a Matisse oven. The clamp frame was then placed on the guide frame, and the Matisse oven (model LTF) was adjusted to 200 °C. Once this temperature was reached, the frame was preheated for 15 seconds. A knife coater was then inserted into the clamping mechanism, and the knife gap was adjusted by preliminary experiments so that the film thickness after gelation was 1 mm (+ / - 0.05 mm). An adhesive strip was attached to the leading edge of the paper to collect excess plastisol. Next, the plastisol was applied in front of the coating knife, and the guide frame was stretched over the clamp-released paper by the coating knife (speed 3 m / min). The coating knife was then removed, and the adhesive strip containing the excess plastisol was removed. The clamp frame was then moved into the oven. After gelation (200 °C for 2 minutes), the frame was again removed from the oven, and after cooling, the film was removed from the paper.

[0077] Example 15: Film Mass Loss Six dumbbell specimens (type S2 according to DIN 53504) per formulation from Example 14 were each weighed after conditioning overnight under standard climate (23°C, 50% relative humidity). The dumbbell specimens were then stored at 80°C on trays (28 x 20 x 6 cm) filled with activated carbon suspended in a convection-operated heating cabinet with a minimum gap of 20 mm. After 7 or 14 days, the dumbbell specimens were removed and stored overnight in a desiccator before being weighed. The mass loss was determined by subtracting the weight of the individual dumbbell specimens. Table 8 shows the average mass loss (%) for the six measurements per formulation. Table 8: Mass loss of films in air (80°C)

[0078] [Table 8] *inventive The mass loss of films containing the triesters of the present invention is less than the mass loss of films containing the corresponding trialkylcyclohexane-1,2,4-tricarboxylic acids.

[0079] Example 16: Glass transition temperature of film The glass transition temperature was determined by DMTA measurements according to DIN 65583 using an Anton Paar MCR302 rheometer. Under constant dynamic mechanical conditions (1 Hz, 0.3% deformation), the viscoelastic properties of the films were recorded as a function of temperature (temperature gradient from -100 to +50°C) and the storage modulus, loss modulus and loss factor. The maximum value of the loss modulus was interpreted as the glass transition temperature. The following table shows the average values ​​of duplicate measurements in each case. Table 9: Glass transition temperature of the film Tg °C

[0080] [Table 9] The low temperature flexibility of the esters according to the invention is clearly improved compared to the comparative compounds, as evidenced by the lower glass transition temperatures.

[0081] Example 17: Preparation of dry blends, rolled sheets and pressed plaques The test specimens required in the following examples are prepared by dry mixing, calendering, and pressing the following formulations: Table 10: Dry Blend Formulations

[0082] [Table 10] Tri(2-ethylhexyl) trimellitate: Eastman Chemical Company, purity >99% Tri(isononyl) trimellitic acid ester: UPC Technology, Taiwan, purity >98% Dry mixtures, called dry blends, can be used to prepare, for example, cable and wire insulation, hoses or flooring and roofing membranes after thermoplastic processing (eg, calendering or extrusion). The dry blend was prepared in a Brabender planetary mixer. Brabender The "Winmix" software was used to set the following parameters in the planetary mixer:

[0083] [Table 11] The temperature in the mixing vessel was 88°C after a 1-hour equilibration period. After the planetary mixer performed its internal calibration, pre-weighed solid ingredients (PVC, stabilizer) in a PE beaker on an analytical balance at four times the amount (four times the amount in g based on Table 10 for phr) were added to the mixing vessel via the solid funnel and the filling stub present in the Brabender mixing vessel. The program was started, the powder mixture was stirred, and after 9 minutes of equilibration in the mixing vessel, four times the amount of liquid ingredients in the PE beaker on the balance were similarly weighed and added via the liquid funnel and the filling stub present in the Brabender mixing vessel. The mixture was stirred in the planetary mixer for an additional 20 minutes. After the program was completed, the completed dry mixture (dry blend) was removed.

[0084] The dry blend was used to prepare rolled sheets. The rolled sheets were prepared on a Collin W150AP calender. The Collin calender was equipped with an automatic sample turner, the temperature of which was controlled by an additional oil thermostat. The calender was controlled using Collin software.

[0085] The roll sheets were prepared using a five-step program:

[0086] [Table 12] Once the roll temperature was reached, the roll gap was calibrated. The roll gap was adjusted to 0.2 mm, 160 g of each dry blend was weighed and introduced into the roll gap while the rollers were stationary, and the measurement was started. The program was started. Compressed plaques were produced in a Collin Laboratory Press. Prefabricated roll sheets (see above) were used to produce the compressed plaques. The lateral edges of the roll sheets were removed using a cutter, after which the roll sheets were cut into pieces measuring approximately 14.5 x 14.5 cm. For pressed plaques with a thickness of 1 mm, in each case two roll sheet pieces were placed one on top of the other on a stainless steel press frame measuring 15 x 15 cm.

[0087] Compression plaques were prepared using a three-step program:

[0088] [Table 13] Example 18: Glass Transition Temperature of Compressed Plaques The glass transition temperature was determined by DMTA measurements according to DIN 65583 using an Anton Paar MCR302 rheometer. Under constant dynamic mechanical conditions (1 Hz, 0.3% deformation), the viscoelastic properties of the films were recorded as a function of temperature (temperature gradient from -100 to +50°C) and the storage modulus, loss modulus and loss factor. The maximum value of the loss modulus was interpreted as the glass transition temperature. The following table shows the average values ​​of duplicate measurements in each case. Table 11: Glass transition temperature of compressed plaques Tg °C

[0089] [Table 14] The low temperature flexibility of the esters according to the invention is higher than that of the comparative compounds, as evidenced by the lower glass transition temperatures. Good low temperature flexibility is particularly relevant for outdoor applications.

[0090] Example 19: Mass loss of compressed plaques Six test specimens were punched from each formulation in the form of S2-type tensile specimens from the compressed plaques of Example 17, conditioned overnight in a desiccator, and then weighed. The test specimens were then stored suspended in a convection-operated heating cabinet at 135°C on trays (28 x 20 x 6 cm) filled with activated carbon with a minimum gap of 20 mm. After 14 days, the test specimens were removed and stored overnight under standard conditions before being weighed. The difference in the measured mass for each test specimen was taken as the mass loss. Table 12 shows the average (%) of the three measurements for each formulation. Table 12: Mass loss of compressed plaque in air (after 14 days storage at 135°C) mass%

[0091] [Table 15] The mass loss of compressed plaques containing the triesters of the present invention is less than the mass loss of films containing the corresponding trialkylcyclohexane-1,2,4-tricarboxylic acid or the corresponding trialkyltrimellitic ester.

Claims

1. Tri-esters of cyclohexane tripropionic acid, each of which contains an ester group comprising a propionic acid moiety and an alcohol moiety, wherein the three alcohol moieties of the three ester groups are each alkyl containing 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms but no heteroatoms other than the oxygen of the functional group of the ester group, and the alcohol moieties have the same number of carbon atoms in one molecule; one or more polymers A composition comprising:

2. The composition of claim 1, wherein the triester of cyclohexane tripropionic acid is a triester of cyclohexane-1,2,4-trippropionic acid or a triester of cyclohexane-1,3,5-trippropionic acid.

3. The composition of claim 1 or 2, wherein the alcohol moiety does not contain any multiple bonds.

4. The composition according to any one of claims 1 to 3, wherein all of the alcohol moieties present in one molecule have the same molecular formula and simultaneously have the same or different structural formulas.

5. The composition of any one of claims 1 to 4, comprising a mixture of at least two cyclohexane tripropionic acids.

6. 6. The composition of claim 5, wherein the at least two cyclohexane tripropionic acids have different molecular and / or structural formulas.

7. The triester is: Bird ( ｉｓｏ pentyl)cyclohexane-1,2,4-tripropionic acid, tri(2-methylbutyl)cyclohexane-1,2,4-tripropionic acid, tri(3-methylbutyl)cyclohexane-1,2,4-tripropionic acid, tri( ｎ hexyl)cyclohexane-1,2,4-tripropionic acid, tri( ｉｓｏ hexyl)cyclohexane-1,2,4-tripropionic acid, tri( ｎ heptyl)cyclohexane-1,2,4-tripropionic acid, tri( ｉｓｏ heptyl)cyclohexane-1,2,4-tripropionic acid, tri( ｎ octyl)cyclohexane-1,2,4-tripropionic acid, tri( ｉｓｏ octyl)cyclohexane-1,2,4-tripropionic acid, tri(2-ethylhexyl)cyclohexane-1,2,4-tripropionic acid, tri( ｎ nonyl)cyclohexane-1,2,4-tripropionic acid, tri( ｉｓｏ nonyl)cyclohexane-1,2,4-tripropionic acid, tri( ｎ decyl)cyclohexane-1,2,4-tripropionic acid, tri( ｉｓｏ decyl)cyclohexane-1,2,4-tripropionic acid, tri(2-propylheptyl)cyclohexane-1,2,4-tripropionic acid; Bird ( ｎ pentyl)cyclohexane-1,3,5-tripropionic acid, tri( ｉｓｏ pentyl)cyclohexane-1,3,5-tripropionic acid, tri(2-methylbutyl)cyclohexane-1,3,5-tripropionic acid, tri(3-methylbutyl)cyclohexane-1,3,5-tripropionic acid, tri( ｎ hexyl)cyclohexane-1,3,5-tripropionic acid, tri( ｉｓｏ hexyl)cyclohexane-1,3,5-tripropionic acid, tri( ｎ heptyl)cyclohexane-1,3,5-tripropionic acid, tri( ｉｓｏ heptyl)cyclohexane-1,3,5-tripropionic acid, tri( ｎ octyl)cyclohexane-1,3,5-tripropionic acid, tri( ｉｓｏ octyl)cyclohexane-1,3,5-tripropionic acid, tri(2-ethylhexyl)cyclohexane-1,3,5-tripropionic acid, tri( ｎ nonyl)cyclohexane-1,3,5-tripropionic acid, tri( ｉｓｏ nonyl)cyclohexane-1,3,5-tripropionic acid, tri( ｎ decyl)cyclohexane-1,3,5-tripropionic acid, tri( ｉｓｏ tri(decyl)cyclohexane-1,3,5-tripropionic acid, and tri(2-propylheptyl)cyclohexane-1,3,5-tripropionic acid; The composition of any one of claims 1 to 6, selected from the group consisting of:

8. A plasticizer for polymers comprising the composition of any one of claims 1 to 7.

9. 8. The composition of any one of claims 1 to 7, wherein the at least one polymer is selected from the group consisting of polyvinyl chloride, polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfide, polylactic acid (PLA), polyhydroxybutyral (PHB), nitrocellulose, and copolymers of vinyl chloride with vinyl acetate or butyl acrylate.

10. 10. The composition of any one of claims 1 to 7 and 9 which is a component of an adhesive, sealing compound, coating composition, lacquer, paint, plastisol, dry blend, foam, synthetic leather, flooring, flooring on top or in a foamed layer thereof, roofing membrane, soffit protection, textile covering, cable, wire insulation, hose, extruded article, film, automotive interior article, wallpaper, ink, toy, contact sheet, food packaging or medical article, tubing protection or blood bag.

11. 9. Use of the plasticizer according to claim 8 as a plasticizer for polymers.

12. 12. The use according to claim 11, wherein the polymer is PVC.

13. 13. Use according to claim 11 or 12, wherein triesters of cyclohexane tripropionic acid, each having an alcohol moiety containing 7 to 12 carbon atoms, are used as polymer plasticizing compounds in high temperature applications.

14. 13. Use according to claim 11 or 12, wherein triesters of cyclohexane tripropionic acid, each having said alcohol moieties containing 5 to 9 carbon atoms, are used as polymer plasticizing compounds in plastisol applications.

15. A process for the preparation of a composition according to any one of claims 1 to 7 and 9, comprising: - ring hydrogenation of the corresponding triester of benzenetrippropionic acid; - transesterification of said trialkyl ester of cyclohexane tripropic acid with at least one alcohol containing 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, wherein the alcohol of the alcohol moiety of said trialkyl ester incorporated has a higher boiling point than the alcohol of the alcohol moiety that is replaced in the context of the transesterification; - esterification of cyclohexane tripropionic acid with at least one alcohol containing 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; - alkoxycarbonylation of trivinylcyclohexane with at least one alcohol containing 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; The process includes:

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