Triester of cyclohexanetripropionic 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] This invention relates to the preparation and use of cyclohexanetripionic acid as a reagent and a polymer plasticizer. [Background technology]

[0002] Polymer plasticizers are added to improve processability and to adapt application-related properties to specific requirements. Various plasticizers with different effect profiles are available to achieve specific desired properties. Phthalate ester compounds 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, meaning they are more or less suitable for different plasticizer applications. For example, phthalate esters with short-chain alcohol portions, such as dibutyl phthalate and dipentyl phthalate, are advantageous because of their low gelation temperature, and are therefore used as fast-acting gelling agents. However, these phthalate esters are highly volatile and unsuitable for other applications. Phthalate esters with long-chain alcohol portions, such as diisononylphthalate (DINP), actually have inferior gelation properties compared to their lighter congeners, and while they have the advantage of low volatility, this volatility is still too high for certain applications requiring high temperature tolerance. Di(tri)decyl phthalate is relatively low-volatility, but this phthalate is not sufficient for many high-temperature applications. Phthalates with more than 13 carbon atoms in the alcohol portion have low polymer compatibility, and the corresponding polymer-phthalate mixtures tend to separate. Therefore, none of the phthalate plasticizers with more than 13 carbon atoms in the alcohol portion are used as plasticizers, for example, in high-temperature cables.

[0004] Since trimellitate plasticizers have lower volatility compared to phthalate esters, they are used in high-temperature applications. Non-patent document 1, which is also a textbook, describes trimellitate esters having an alcohol moiety containing 7 to 9 carbon atoms of trimellitic acid or a mixture of C6- and C8-esters or C7-, C8- and C9-esters for commercial purposes, and emphasizes tris(2-ethylhexyl) trimellitate as the most important trimellitate ester. Even this trimellitate ester often has too high volatility for use in high-temperature cables.

[0005] Patent document 1 discloses trimellitate esters, and cyclohexane-1,2,4-tricarboxylic acid, and their suitability as plasticizers.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Non-Patent Documents

[0007]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] Here, an object of the present invention is to provide a novel group of plasticizers that generally have a wide range of properties, that is, can be used in many different applications. The novel group of plasticizers may preferably include agents having extremely good gelling ability and agents having excellent high-temperature properties. Usually, the novel group of plasticizers may preferably be superior to trimellitate esters in high-temperature applications such as cables.

Means for Solving the Problems

[0009] The objective is achieved by the triester of cyclohexanetripropionic acid described in claim 1. The present invention relates to a triester of cyclohexanetripropionic acid in which each of the three alcohol moieties of the three ester groups contains 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.

[0010] All trysters of cyclohexanetripropionic acid as carboxylic acid esters are formally formed from a carboxylic acid and an alcohol, thereby the ester containing an acidic moiety and an alcohol moiety. The tryster of cyclohexanetripropionic acid of the present invention consists of a cyclohexanetripropionic acid moiety and three alcohol moieties. Each of the alcohol moieties contains 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.

[0011] The triester of cyclohexanetripropionic acid of the present invention is also referred to below by its abbreviation as the triester of the present invention.

[0012] Surprisingly, typical examples of this novel group of plasticizers were found to be suitable for plastisol applications, exhibiting low gelation temperatures and offering advantages as rapid gelling agents, while other typical examples within this group were found to be advantageous for thermoplastic applications. In both plastisol and thermoplastic applications, typical examples of this group exhibit low mass loss. Good low-temperature flexibility (low glass transition temperature) can be achieved with typical examples of this group.

[0013] In addition to the desired suitability of typical examples of the novel plasticizer group for high-temperature applications, these typical examples enable low viscosity in plastisol applications, along with the advantageous thickening properties of the plastisol in question.

[0014] The three propionate groups of the ester of the present invention can be bonded to various positions on the cyclohexane ring. 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, and more particularly a triester of cyclohexane-1,2,4-tripropionic acid.

[0015] The alcohol portion of the cyclohexanetripropionic acid triester may be a cyclic or acyclic alkyl group having or not having a functional group containing multiple bonds. Here, it is irrelevant whether the functional group originates from the alcohol used in the preparation of the triester of the present invention or is subsequently inserted into the triester molecule. Similarly, the alcohol portion may be absent or contain an aromatic ring with one or more functional groups. The alcohol portion of the triester of the present invention preferably does not contain other heteroatoms other than the oxygen atom of the ester functional group, and does not contain multiple bonds. The preparation of the obtained triester is formally based on an alkanol, preferably an acyclic alkanol, in this alcohol portion. Alkanol is readily available, which has the advantage of being particularly low-cost.

[0016] The present invention preferably relates to triesters of cyclohexane-1,2,4-tripropionic acid, in which each of the three alcohol moies of the three ester groups contains 2 to 9, preferably 4 to 9, 5, 6, 7, 8, or 9 carbon atoms. The reagents exhibit good gelation properties, and the plastisols prepared using them are characterized by low plastisol viscosity, which increases only slightly over time. In applications of the plastisols, such as film applications, only a small amount of mass is lost in air. As is evident from the low glass transition temperature, the low-temperature flexibility of test specimens containing the triesters is higher than that of comparative compounds. However, the triesters according to the present invention are preferably triesters of cyclohexane-1,2,4-tripropionic acid, or triesters of cyclohexane-1,3,5-tripropionic acid, particularly triesters of cyclohexane-1,2,4-tripropionic acid in which the alcohol moiety is morphologically derived, preferably from an acyclic alkanol.

[0017] The present invention also preferably relates to triesters of cyclohexane-tripropionic acid, in which each of the three alcohol moieties of the three ester groups contains 7 to 12, preferably 8 to 10, and particularly 8 or 9 carbon atoms. The triesters are characterized by very low mass loss at high temperatures, i.e., are very suitable for high-temperature applications. Furthermore, the low-temperature flexibility of test specimens containing the triesters is higher than that of comparative compounds. However, the triesters according to the present invention are preferably triesters of cyclohexane-1,2,4-tripropionic acid, or triesters of cyclohexane-1,3,5-tripropionic acid, particularly triesters of cyclohexane-1,2,4-tripropionic acid in which the alcohol moieties are formally produced from a cyclic alkanol, preferably.

[0018] The triesters of the present invention preferably contain two or three alcohol moieties having the same empirical formula within a single molecule. In this case, the "same empirical formula" alcohol moieties within a single triester have the same arrangement of atoms or different structures, i.e., isomer alcohol moieties. Preferably, all alcohol moieties present in a single molecule of the triester of the present invention have the same empirical formula and simultaneously have the same or different structural formulas. The triesters of the present invention, in which the alcohol moieties have the same empirical formula and different structural formulas, contain isomer alcohol groups. Such triesters are also advantageously liquid at low temperatures.

[0019] Preferred triesters of cyclohexanetripropionic acid, namely the triesters of cyclohexane-1,2,4-tripropionic acid, include formula I:

[0020] [Formula 1] There is a structure represented by , where the R group has the same empirical formula and at the same time has the same structural formula It has one or a different structural formula.

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

[0022] The present invention further relates to a mixture of at least two triesters of cyclohexanetripropionic acid. In this case, the at least two triesters according to the present invention may differ in their empirical formula, structural formula, or both. An example of a mixture in which the empirical formula differs and the mixture contains at least two triesters according to the present invention is tri( nThe mixture comprises pentyl)cyclohexane-1,2,4-tripropionic acid and tri(2-ethylhexyl)cyclohexane-1,2,4-tripropionic acid. If at least two esters of the present invention differ with respect to their structural formulas, then 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, for example. Alternatively, in addition to possible differences in the position of the propion ester group on the cyclohexane ring, the mixture may contain at least two triesters of the present invention that include alcohol moieties of the "same empirical formula" but with different structures, i.e., isomer alcohol moieties. For example, the mixture may contain one triester of the present invention in which the alcohol moiety is always linear and the alcohol moiety is uniformly branched. An example of such mixture is tri( n This is a combination of 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( iso It may also be a more complex mixture containing pentyl)cyclohexane-1,3,5-tripropionic acid.

[0023] The prefix "iso" indicates the fact that it is a mixture of isomers with a common number of carbon atoms. Therefore, 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 proportions in which each isomer exists. The same triester as in the present invention is tri( iso If it is not exclusively present in the isomer mixture of alkyl)cyclohexanetripropionate salts, that is, a mixture of at least two triesters relating to the present invention with different structural formulas.

[0024] Preferred triesters according to the invention or mixtures according to the invention are as follows: 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, tri(3-methylbutyl) cyclohexane-1,2,4-tripropionate, tri( n hexyl) cyclohexane-1,2,4-tripropionate, tri( iso hexyl) cyclohexane-1,2,4-tripropionate, tri( n heptyl) cyclohexane-1,2,4-tripropionate. Tri( iso heptyl) cyclohexane-1,2,4-tripropionate, tri( n octyl) cyclohexane-1,2,4-tripropionate, tri( iso octyl) cyclohexane-1,2,4-tripropionate, tri(2-ethylhexyl) cyclohexane-1,2,4-tripropionate, tri( n nonyl) cyclohexane-1,2,4-tripropionate, tri( iso nonyl) cyclohexane-1,2,4-tripropionate, tri( n decyl) cyclohexane-1,2,4-tripropionate, tri( iso decyl) cyclohexane-1,2,4-tripropionate, tri(2-propylheptyl) cyclohexane-1,2,4-tripropionate; Tri(n-butyl) cyclohexane-1,3,5-tripropionate, tri(methylpropyl) cyclohexane-1,3,5-tripropionate, tri( n pentyl) cyclohexane-1,3,5-tripropionate, tri( isoPentyl)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 described above, the esters of the present invention have advantageous properties when used as plasticizers for polymers. Specifically, the present invention further relates to a plasticizer for polymers comprising the triesters of the present invention or a mixture of the present invention (containing at least two of the triesters), and optionally, at least one further polymer plasticizing compound. The plasticizer is particularly suitable for PVC.

[0026] The present invention also relates to a composition comprising a triester according to the present invention or a mixture according to the present invention (containing at least two of such triesters) or a plasticizer according to the present 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 having an alkoxy group of a branched or unbranched alcohol with 1 to 10 carbon atoms, homo or copolymers based on acrylonitrile or cyclic olefins, polyvinylidene chloride (PVDC), polyacrylate, especially polymethyl methacrylate (PMMA), polyalkyl methacrylate (PAMA), polyurea, silylated polymers, fluoropolymers, especially polyvinylidene fluoride. Nylidene (PVDF), polytetrafluoroethylene (PTFE), polyvinyl acetate (PVAc), polyvinyl alcohol (PVA), polyvinyl acetal, especially polyvinyl butyral (PVB), polystyrene polymer, especially polystyrene (PS), expandable polystyrene (EPS), acrylonitrile-acrylic (ASA), styrene-acrylonitrile-butadiene-styrene (ABS), styrene-maleic anhydride (SMA), styrene-methacrylic acid copolymer, polyolefin, especially polyethylene (PE) or polypropylene (PP), thermoplastic polyolefin (TPO), polyethylene The material is 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, particularly polylactic acid (PLA), polyhydroxybutyral (PHB), polyhydroxyvaleric acid (PHV), polyester, starch, cellulose and cellulose derivatives, particularly nitrocellulose (NC), ethylcellulose (EC), cellulose acetate (CA), cellulose acetate / butyrate (CAB), rubber, and silicone.

[0028] In preferred embodiments, at least one polymer in the composition, preferably at least 90% by mass of the 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 of the present invention containing one or more polymers is preferably 5 to 150 parts by mass, preferably 10 to 120 parts by mass, particularly preferably 15 to 110 parts by mass, and particularly preferably 20 to 100 parts by mass, per 100 parts by mass of polymer. However, the composition containing one or more polymers may also contain less than 20 parts by mass of the triester according to the present invention per 100 parts by mass of polymer.

[0030] The compositions of the present invention are preferably components of adhesives, sealants, coatings, lacquers, paints, plastisols, dry blends, foams, synthetic leathers, flooring materials, particularly their top layer or foam layer, roof membranes, underbody protection, textile coverings, cables, wire insulation, hoses, extruded articles, films, automotive interior articles, wallpaper, inks, toys, contact sheets, food packaging, or medical articles, particularly tube protection or blood bag components.

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

[0032] The use, as a result, is preferably the use of the triesters of the present invention or a mixture of the present invention (containing at least two of the triesters) in adhesives, sealants, coatings, lacquers, paints, plastisols, dry blends, foams, synthetic leather, flooring, especially the top layer or foam layer thereof, roof membranes, underlayment, textile coverings, cables, wire insulation, hoses, extruded articles, films, automotive interior articles, wallpaper, inks, toys, contact sheets, food packaging, or medical articles, especially the protection of tubes or blood bags.

[0033] In preferred embodiments, triesters of cyclohexanetripropionic acid, in which the three alcohol portions of the three ester groups each contain 7 to 12 carbon atoms, preferably 8 to 10, and particularly 8 or 9 carbon atoms, are used as polymer plasticizers for high-temperature applications, particularly for high-temperature cables or dashboard components.

[0034] In another preferred embodiment, a triester of cyclohexanetripropionic acid, in which the three alcohol portions of the three ester groups contain 2 to 9 carbon atoms, preferably 4 to 9, 5, 6, 7, 8, or 9, is used as a polymer plasticizer for plastisol applications. Preferably, it is used in textile coatings, wallpaper, synthetic leather, films, roofing membranes, and flooring.

[0035] The triesters of the present invention are as follows: -Ring hydrogenation of the corresponding triester of benzenetripropionic acid; - A transesterification reaction of a trialkyl ester of cyclohexanetripropionic acid with at least one alcohol having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms, wherein the alcohol of the incorporated trialkyl ester's alcohol moiety is greater than the alcohol of the substituted alcohol moiety in the context of the transesterification reaction. High boiling point; - Esterification of cyclohexanetripropionic 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 that includes [the following].

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

[0037] This disclosure preferably includes the following: -Ring hydrogenation of triesters of benzenetripropionic acid, in which the alcohol moiety of the ester group each contains 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms; - A transesterification reaction of a trialkyl ester of cyclohexanetripropionic acid with at least one alcohol having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms, wherein the alcohol of the incorporated trialkyl ester has a higher boiling point than the alcohol of the substituted alcohol moiety in the context of the transesterification reaction; - Esterification of cyclohexanetripropionic 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; This is the preparation of triesters of cyclohexanetripropionic acid according to the present invention.

[0038] For the preparation of the triesters of cyclohexane-1,2,4-tripropionic acid, it is particularly preferable to use cyclohexane-1,2,4 compounds for each.

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

[0040] The present invention is particularly preferably characterized by the following: -Ring hydrogenation of triesters of benzene-1,2,4-tripropionic acid, in which the alcohol moiety of the ester group each contains 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms; -Transesterification of trimethyl ester or triethyl ester of cyclohexane-1,2,4-tripropionic acid by 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; This invention relates to the preparation of a triester of cyclohexane-1,2,4-tripropionic acid.

[0041] In one or more hydrogenation units connected in series, a triester can be obtained by the cyclic hydrogenation of the triester of benzene-1,2,4-tripropionic acid according to the present invention. The hydrogenation unit preferably consists of at least one, preferably two or more, hydrogenation reactors. The at least one hydrogenation reactor is a tubular reactor, A tube bundle reactor, or preferably a shaft oven, may be used. Individual reactors can be operated adiabatically, polytropically, or substantially isothermally, i.e., with a temperature rise of typically less than 10°C. In particular, reactors operating in loop mode are driven quasi-isothermally and operate with a temperature rise of preferably less than 10°C, and especially preferably less than 5°C. One or more hydrogenation units can be operated in loop mode.

[0042] The hydrogenation of benzenetripropionic acid triesters is preferably carried out continuously using a hydrogen-containing gas on a solid catalyst placed in a fixed bed.

[0043] The hydrogenation gas used may be any hydrogen-containing gas mixture that does not contain harmful amounts of catalyst poisons such as carbon monoxide or hydrogen sulfide. In some cases, an inert gas may be used, and it is preferable that the purity of the hydrogen exceeds 95%, and particularly exceeds 98%. The inert gas fraction may be, for example, nitrogen or methane.

[0044] Preferably, the solid hydrogenation catalyst contains at least one metal from the transition group 8 of the periodic table. The active metal from the transition group 8 of the periodic table used is preferably platinum, rhodium, palladium, cobalt, nickel, or ruthenium, or a mixture of two or more of these, with ruthenium being particularly preferred as the active metal. In addition to the above metals, at least one metal from the transition groups 1 and / or 7 of the periodic table may further 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 dioxide, 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 alkali metals, alkaline earth metals and / or sulfur. Preferably, a ruthenium catalyst is used.

[0045] The hydrogenation process is preferably carried out in a liquid / gas mixed phase or simultaneous flow in a liquid phase within a three-phase reactant, where the hydrogenation gas is distributed into the liquid reactant / product stream in a manner known to the present day. For uniform liquid distribution, improved removal of reaction heat and / or high space-time yield, a reactor operating in loop mode is used, with an empty reactor cross-section of 1 m 2 10 to 400 per unit and per hour, preferably 20 to 200, and especially preferably 40 to 150 m 3 It is preferable to operate it under a high liquid load.

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

[0047] The transesterification reaction of the trimethyl ester of cyclohexanetripropionic 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 cyclohexanetripropionic acid with one or more such alcohols, is preferably carried out in the presence of one or two or more catalysts, for example, using a Brønsted acid or base or a Lewis acid or base as a catalyst. Particularly preferred catalysts have been found to be sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, metals, or compounds thereof. Examples of particularly preferred metal catalysts include tin powder, tin(II) oxide, tin(II) oxalate, titanates such as tetraisopropyl or orthotyltetrabutyl orthotitanate, and zirconium esters such as tetrabutylzirconate, and sodium methoxide and potassium methoxide. Santripionic acid can be obtained by hydroxycarbonylation, i.e., by a noble metal-catalyzed reaction of trivinylcyclohexane with CO and H2O.

[0048] Esterification and transesterification processes can be carried out under normal process conditions in a conventional esterification apparatus known to those skilled in the art. The process is preferably carried out at a temperature above the boiling point of the alcohols formed during the reaction, so that they can be removed from the reaction mixture by distillation. Examples of suitable transesterification reactions are described in the Experiments section.

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

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

[0051] [chemical 2] A first charging step of one of the compounds, or a mixture of at least two of the compounds; b) The following ligands (L)

[0052] [C3] and a step of adding a compound containing Pd or a complex containing Pd and ligand (L); c) Addition of an alcohol having 1 to 12 carbon atoms; d) CO supply process; e) A heating step of the reaction mixture from steps a) to d), wherein the compound / mixture from a) is converted into a triester; This process includes [the following].

[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 in step (c) is preferably free of oxygen and other heteroatoms, free of multiple bonds, and is particularly methanol, ethanol, n Butanol, methylpropanol, n Pentanol, iso Pentanol, 2-methylbutanol, 3-methylbutanol, n Hexanol, iso Hexanol, n Heptanol, iso Heptanol, n Octanol, isoOctanol, 2-ethylhexanol, n Nonanol, iso Nonanol, n Decanol, iso Selected from decanol and 2-propylheptanol.

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

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

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

[0057] Acid value: The acid value was measured 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: Approximately 23.8 ml / min Furnace temperature program (Duration: 50°C (1 minute), 7.5°C / min to 350°C (hold for 30 minutes)) Injector: 350℃ Detector (FID): 400℃ Injection volume: 1.0 μl The components in the sample chromatogram were identified using a comparative solution of the related ester. The signals in the sample chromatogram were then normalized to 100%. Molar ratios were determined by approximating them sufficiently 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] [C4] [Pd(acac)2] (15.2 mg, 0.1 mol%), (L) (the above formula, 103 mg, 0.4 mol%), and p-toluenesulfonic acid (PTSA, 143 mg, 1.5 mol%) were placed in a 100 ml steel autoclave under an argon atmosphere. Then, methanol (MeOH, 30 ml) and trivinylcyclohexane(i) (8.1 g, 50 mmol) were injected by syringe. The autoclave was flushed three times with CO and then pressurized to a CO pressure of 40 bar. The reaction was carried out at 110 °C for 10 hours. Next, the autoclave was cooled to room temperature and reduced in pressure. The desired product was distilled (10 -3 The material was purified by bar (at 165°C) and characterized by 1H-, 13C-NMR and HR-MS (15.6g, yield 91%, purity 98%).

[0059] [C5] [Examples 1-5: Preparation of trialkylcyclohexane-1,2,4-tripropionic acid according to the present invention] In a distillation apparatus including a Raschig ring column fitted with an immersion tube, thermometer, and condenser, the amount of trimethylcyclohexane-1,2,4-tripropionic acid is initially filled, and the amount of alcohol m a The suspension was then purged with nitrogen (6 l / hour) through the immersion tube for at least 1 hour, and 0.15 mass% tetra- n Butyl butyl titanate (Si GMA Aldrich, purity >97%, was added based on the mass of tripionate. Nitrogen (6 L / H) was continuously diffused until the end of the reaction, and the mixture was slowly heated with stirring until it boiled. Methanol was produced from the reaction via a distillation head and continuously removed up to a maximum temperature of 61°C to 63°C. If the maximum temperature exceeded 68°C, the distillate was not removed. During the transesterification reaction, the amount of methanol mm The following was produced (reaction time t). During the reaction, samples were taken every hour and analyzed by gas chromatography. If less than 0.5 area percent of monomethyl ester was detected by GC analysis, the heating medium was removed and the contents of the reaction flask were cooled to 80°C while introducing nitrogen.

[0060] For the process, the crude product was transferred to a distillation apparatus equipped with a Claisen adapter and a vacuum partial pressure regulator. Excess alcohol was removed by distillation under reduced pressure (approximately 1 mbar) at a bottom temperature of approximately 160°C to 180°C (tributyl and tripentyl esters approximately 160°C, tri(2-ethylhexyl) esters and tri(isononyl) esters 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 at 80°C for 15 minutes by nitrogen spraying (6 l / hour) with three times the volume of base (10% NaOH aqueous solution, Merck NaOH, purity >99%). Then, based on the mass of the flask contents, 2% by mass of activated carbon (Cabot Norit Nederland BV, CAP Super) was packed and stirred for 5 minutes. The remaining volatile fraction was removed again by nitrogen inlet under vacuum and at approximately 160°C or 180°C (see above), and the nitrogen flow was adjusted so that the pressure did not exceed 20 mbar. If the residual alcohol content determined by GC analysis was less than 0.025 area%, the resulting crude product was cooled and filtered into a suction bottle under reduced pressure through a Buchner funnel containing a pre-compressed filtration cake (perlite type D14) of filter paper and filtration aid.

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

[0062] Specific characteristics of individual synthesis: In the preparation of tri(2-ethylhexyl)ester, tri(isononyl)ester, and tri(2-propylheptyl)ester, reduced pressure was applied stepwise while maintaining reflux (at 240°C) during the transesterification process. In this case, the top temperature decreased slowly as the pressure decreased. Table 1: Details of the preparation of trialkylcyclohexane-1,2,4-tripropionic acid according to the present invention

[0063] [Table 1] * Inventive n-butanol: Sigma-Aldrich, purity >99.4% Isopentanol: A mixture of n molecules of pentanol (Sigma-Aldrich, purity >99%) and 2-methylbutanol (Sigma-Aldrich, purity >99%) in a 1:1 molar ratio. 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 acid] In a distillation apparatus equipped with immersed tubes, a thermometer, and a condenser fitted with a moisture separator, the initial load is milliseconds of cyclohexane-1,2,4-tricarboxylic acid (Ct acid, >97%), and the amount of alcohol m a The mixture was suspended in [a solution]. The apparatus was purged with nitrogen (6 L / H) through an immersion tube for at least 1 hour, and 0.15% by mass of tetra-n-butyltiantate butyl (Sigma Aldrich, purity >97%) was added based on the mass of cyclohexane-1,2,4-tricarboxylic acid. Nitrogen (6 L / H) was continued to diffuse until the end of the reaction, and the mixture was slowly heated with stirring until it boiled. The resulting reaction water was continuously removed from the reaction through a water separator. If continuous reflux is not available, cyclohexane m [a solution] was used as an azeotropic agent. c A certain amount was added. During the esterification process, the amount of water (m w ) was produced (reaction time t). After reaching the theoretical amount of reaction water, samples were taken every 30 minutes and the acid value was measured. If an acid value <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 the process, the crude product was transferred to a distillation apparatus including a Claisen adapter with a vacuum partial pressure regulator. The distillation was performed under reduced pressure (approximately 1 mbar) and at a bottom temperature of approximately 160°C to 180°C (Tri( n Excess alcohol was removed by distillation using butyl ester and tri(isopentyl) ester at approximately 160°C, and tri(2-ethylhexyl) ester, tri(isononyl) ester and tri(2-propylheptyl) ester at approximately 180°C. The mixture was then cooled again under a nitrogen atmosphere. After measuring the acid value of the flask contents, the contents were stirred at 80°C for 15 minutes by nitrogen spraying (6 l / hour) with three times the volume of base (10% NaOH aqueous solution, Merck NaOH, purity >99%). Subsequently, based on the mass of the flask contents, 2% by mass of activated carbon (Cabot Norit Nederland BV, CAP Super) was packed in and stirred for 5 minutes. The remaining volatile fraction was removed again by nitrogen inlet under vacuum at approximately 160°C or approximately 180°C (see above), and the nitrogen flow was adjusted so that the pressure did not exceed 20 mbar. If the residual alcohol content determined by GC analysis was less than 0.025 area%, the resulting crude product was cooled and filtered into a suction bottle under reduced pressure through a Buchner funnel containing a pre-compressed filtration cake (perlite type D14) of filter paper and filtration aid.

[0065] The amount mp of trialkylcyclohexane-1,2,4-tricarboxylic acid was obtained with the purity (%) shown in Table 2.

[0066] Specific characteristics of individual synthesis: Bird ( n Preparation of butyl ester: In this experiment, based on the mass of cyclohexane-1,2,4-tricarboxylic acid, 0.15% by mass of sulfuric acid (Sigma-Aldrich, purity 95-97%) was used to tetra- n It was added together with butyl titanate. Furthermore, if an acid value of less than 1 mg KOH / g was detected (not less than 0.1 mg / g for KOH), nitrogen was introduced and the contents of the reaction flask were cooled to 80°C. Bird ( n Butyl ester and tri( isoPreparation of pentyl ester: At the start of the reaction, Tetra- n Only half of the butyl titanate and each alcohol were added initially, and the remaining amount was 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 from Examples 1-10] Viscosity was determined using a Stabbinger viscometer (Anton Paar SVM3000), an improved version of the classic Couette rotational viscometer. Following the instructions, the esters were individually injected to avoid air bubbles and measured at 20°C. The intrinsic viscosity of the esters is shown in Table 3. Table 3: Intrinsic viscosity [mPa·s] of esters from Examples 1-10 at 20°C

[0068] [Table 3] [Example 12: Preparation of Plastisol] PVC plastisol was prepared, for example, for use in the preparation of topcoat films for floor coverings. The values ​​for each plastisol formulation are in units of mass. Table 4 lists the polymer composition formulations. Table 4: Plastisol preparations

[0069] [Table 4] First, the mass of the liquid component was measured, followed by the mass of the powder component, and then placed in a PE beaker. The mixture was manually stirred with an ointment spatula until no unmoistened powder remained. The mixed beaker was then mounted on the clamping device of a dissolving stirrer. After switching on the stirrer, the speed was slowly increased to approximately 2000 rpm (revolutions per minute). Meanwhile, the plastisol was carefully degassed, and the pressure was kept 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, and the pressure was reduced to below 20 mbar. This allowed us to homogenize the plastisol with a constant energy input. Subsequently, for further study, the plastisol was immediately equilibrated to 25.0°C in a climate-controlled cabinet.

[0070] [Example 13: Measurement of thickening behavior] The viscosity of the plastisol prepared in Example 12 was measured using rotation mode and the CC27 measurement system with the associated software using a PhysicaMCR101 rheometer (Anton Paar G Measured at ermany GmbH. During the measurement, the following points were monitored:

[0071] -100s -1 Then, a 60-second preliminary shear test was conducted (no measurements were taken during this time); -Shear rate 200s -1 from 0.1s -1 The measurement points for downward movement were set at 30 points, and the measurement period was set at 10 seconds. Measurements were performed after storage for 2 hours, 24 hours, and 7 days. Plastisol was stored at 25°C during the measurement period. The thickening behavior of plastisol was determined based on the viscosity value after 2 hours, using the viscosity increase rates after 24 hours and 7 days, for 1, 10, and 100 s. -1 The measurement was taken using the shear rate. Table 5: Plastisol 1s of Example 12 -1 Thickening behavior in

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

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

[0074] [Table 7] *According to the present invention The plastisol viscosity of trialkylcyclohexane-1,2,4-tripropionic acid according to the present invention is lower than that of the comparative ester. Furthermore, the increase in viscosity of trialkylcyclohexane-1,2,4-tripropionic acid over time is not as pronounced as in the comparative ester. Due to these advantageous properties, the triester of the present invention can be used even after being left standing for a long time without the addition of viscosity-reducing additives, thereby saving the time and effort associated with the use of such additives.

[0075] [Example 14: Film Preparation] Each of the plastisols prepared in Example 12 was processed to obtain a 1 mm thick film.

[0076] For this purpose, first, high-gloss release paper (Sappi, Italy) was trimmed to a size of 30 x 44 cm and inserted into the clamp frame of the LTSV coating apparatus for the Matisse oven. Then, the clamp frame was placed on the guide frame, and the Matisse oven (model LTF) was set to 200°C. Once this temperature was reached, the frame was preheated for 15 seconds. Next, the knife coater was inserted into the clamping mechanism, and the knife gap was adjusted by preliminary experiments so that the film thickness after gelation would be 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 spread by stretching the guide frame onto the released paper with the coating knife (speed 3 m / min). Then, the coating knife was removed and the adhesive strip containing the excess plastisol was removed. Next, the clamp frame was moved into the oven. After gelation (200°C for 2 minutes), the frame was moved out of the oven again, and after cooling, the film was removed from the paper.

[0077] [Example 15: Mass loss of film] Six dumbbell test specimens (Type S2 according to DIN 53504) per formulation from Example 14 were prepared overnight under standard climate conditions (23°C, 50% relative humidity) and then weighed. Subsequently, the dumbbell test specimens were stored at 80°C on trays (28 × 20 × 6 cm) filled with activated carbon to a minimum gap of 20 mm, suspended in a convection-operated heating cabinet. After 7 or 14 days, the dumbbell specimens were removed, stored overnight in a desiccator, and then their mass was measured. Mass loss was determined by subtracting the mass of each individual dumbbell test specimen. Table 8 shows the average (%) mass loss measured six times for each formulation. Table 8: Mass loss of film in air (80°C)

[0078] [Table 8] *inventive The mass loss of the film containing the triester of the present invention is smaller than that of the film containing the corresponding trialkylcyclohexane-1,2,4-tricarboxylic acid.

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

[0080] [Table 9] As is evident from the low glass transition temperature, the low-temperature flexibility of the ester according to the present invention is clearly improved compared to the comparative compound.

[0081] [Example 17: Preparation of dry blend, roll sheet, and press plaque] The test specimens required in the following examples are prepared by dry mixing (dry blend preparation), calendering (rolling), and pressing of the following formulations: Table 10: Dry Blend Formulations

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

[0083] [Table 11] The temperature inside the mixing vessel was 88°C after a 1-hour equilibration period. After the planetary mixer performed internal calibration, four times the amount (four times the amount in g based on Table 10 of phr) of the solid components (PVC, stabilizer) were pre-weighed into a PE beaker on the analytical balance and supplied to the mixing vessel via a solid funnel and a filling stub present in the Bravender mixing vessel. The program was started, the powder mixture was stirred, and equilibrated in the mixing vessel for 9 minutes. Similarly, four times the amount of the liquid components in the PE beaker on the balance was weighed and supplied via a liquid funnel and a filling stub present in the Bravender mixing vessel. The mixture was stirred in the planetary mixer for a further 20 minutes. After the program ended, the finished dry mixture (dry blend) was removed.

[0084] A roll sheet was prepared using the dry blend. The roll sheet was prepared on a Korin W150AP calender. The Korin calender is equipped with an automatic sample turner, and its temperature is controlled by an additional oil thermostat. Control was performed using Korin software.

[0085] The roll sheet was prepared using a 5-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 the rollers were placed into the roll gap while remaining fixed to begin measurement. The program was then started. Compressed plaques were fabricated using the Colin Laboratory Press. Compressed plaques were fabricated using prefabricated roll sheets (see above). After removing the lateral edges of the roll sheets with a cutting machine, the roll sheets were cut into small pieces approximately 14.5 x 14.5 cm in size. For each 1 mm thick pressed plaque, two roll sheet pieces were placed on top of a 15 x 15 cm stainless steel press frame.

[0087] A three-stage program was used to create a compressed plaque:

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

[0089] [Table 14] As is evident from the low glass transition temperature, the low-temperature flexibility of the ester according to the present invention is higher than that of the comparative compound. Good low-temperature flexibility is particularly relevant for outdoor applications.

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

[0091] [Table 15] The mass loss of the compressed plaque containing the triester of the present invention is smaller than that of the film containing the corresponding trialkylcyclohexane-1,2,4-tricarboxylic acid or the corresponding trialkyltrimellitic acid 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 ( ｎ butyl)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( 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 from 2 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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