Plasticizer composition containing c4 to c9 alkyl esters of 1,2,4-cyclohexanetripropionic acid and dibutyl terephthalate or dipentyl terephthalate

Abstract

The invention relates to a plasticizer composition containing a compound of formula (1), wherein each of the three alkyl groups R has 4 to 9 carbon atoms, and dibutyl terephthalate or dipentyl terephthalate.

Description

[0001] 202400194

[0002] 1

[0003] Plasticizer composition containing C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid and dibutyl terephthalate or dipentyl terephthalate

[0004] The invention relates to a plasticizer composition containing a compound of formula (1) wherein the three alkyl groups R each have 4 to 9 carbon atoms, and dibutyl terephthalate or dipentyl terephthalate.

[0005] The compounds according to the invention, based on formula (1), are C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid. These esters of 1,2,4-cyclohexanetripropionic acid are generally known and have been described, for example, in EP 3 838 888 A1. It was also mentioned therein that these esters of 1,2,4-cyclohexanetripropionic acid can be used as plasticizers for polymers.

[0006] Although the trialkyl esters of 1,2,4-cyclohexanetripropionic acid are known and their use as plasticizers has been mentioned, there is a continuous need to improve their properties when used as plasticizers. Depending on the application, the requirements for the plasticizer to be used can vary.

[0007] The present invention was based on the objective of providing a plasticizer composition that further improves the properties of the C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid.

[0008] This problem is solved by the plasticizer composition according to claim 1. The invention therefore relates to a plasticizer composition containing a compound of formula (1) 202400194

[0009] 2 wherein the three alkyl groups R each have 4 to 9 carbon atoms, and dibutyl terephthalate or dipentyl terephthalate. Preferred embodiments of the present invention are specified in the dependent claims.

[0010] The compounds according to formula (1) of the invention are therefore C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid. The three alkyl groups R can each be selected independently from the group consisting of a normal butyl group, an isobutyl group, a normal pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a normal hexyl group, an isohexyl group, a normal heptyl group, an isoheptyl group, a normal oxycyl group, an isooctyl group, a normal nonyl group, or an isononyl group. For the purposes of this invention, an isononyl group is understood to be a mixture of linear and branched primary C9 alkyl groups. The same applies to the terms isohexyl group, isoheptyl group, and isodecyl group.

[0011] In a preferred embodiment of the present invention, the three alkyl groups R of the longer-chain trialkyl esters of 1,2,4-cyclohexanetripropionic acid each have the same number of carbon atoms. This means that all three alkyl groups R have 4, 5, 6, 7, 8, or 9 carbon atoms, but not that the three alkyl groups must always be identical. Different isomers of the respective alkyl group can also be present simultaneously, for example, 2-methylbutyl and n-pentyl groups in the case of the C5 alkyl group.

[0012] Within the scope of the present invention, it is particularly preferred that the compound according to formula (1) in the plasticizer composition is a tripentyl ester of 1,2,4-cyclohexanetripropionic acid or a triisononyl ester of 1,2,4-cyclohexanetripropionic acid. The term tripentyl ester of 1,2,4-cyclohexanetripropionic acid includes trialkyl esters of 1,2,4-cyclohexanetripropionic acid in which each of the three alkyl groups is a 2-methylbutyl group, a 3-methylbutyl group, or an n-pentyl group. Preferably, the proportion of n-pentyl groups is at least 55% and at most 95%, based on all (= 100%) of the pentyl groups in the tripentyl ester of 1,2,4-cyclohexanetripropionic acid. The term triisononyl esters of 1,2,4-cyclohexanetripropionic acid also includes mixed esters containing different C9 alkyl groups (isomers of the nonyl group). This is due to their preparation using commercially available isononanol (e.g., from Evonik Oxeno GmbH & Co. KG).KG), which typically represents a mixture of different C9 alcohols (linear and branched). 202400194.

[0013] 3

[0014] The preparation of the longer-chain trialkyl esters of 1,2,4-cyclohexanetripropionic acid according to the invention can be carried out by transesterification of the trimethyl ester of 1,2,4-cyclohexanetripropionic acid with an alcohol having 4 to 9 carbon atoms or by direct esterification of 1,2,4-cyclohexanetripropionic acid with an alcohol having 4 to 9 carbon atoms. If the tripentyl or triisononyl ester of 1,2,4-cyclohexanetripropionic acid is to be prepared, pentanol or isononanol is to be used as the alcohol. The alcohol is used in excess, i.e., in an amount of more than 3 mol per mol of ester component, preferably 3.75 to 5.25 mol of alcohol per mol of ester component. The transesterification and the direct esterification are preferably carried out over an acidic catalyst, for example, inorganic or organic Brønsted or Lewis acids.

[0015] In addition to the compounds listed in formula (1), the plasticizer composition contains dibutyl terephthalate, abbreviated DBT, or dipentyl terephthalate, abbreviated DPT. Both plasticizers are terephthalic acid esters and are commercially available.

[0016] The two substances, i.e., the C4 to C9 alkyl ester of 1,2,4-cyclohexanetripropionic acid as the compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate, can be present in varying amounts in the plasticizer composition according to the invention. It should be clear that the two substances must be present in an amount at which they exert an effect, i.e., where a plasticizing effect occurs. In a preferred embodiment of the present invention, the C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid as a compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate are present in a weight ratio (C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid as a compound according to formula (1) : dibutyl terephthalate or dipentyl terephthalate) of 1 : 99 to 99 : 1, preferably 10 : 90 to 90 : 10, particularly preferably 30 : 70 to 70 : 30 in the plasticizer composition.

[0017] The plasticizer composition according to the present invention can additionally contain an epoxidized oil or an epoxidized alkyl ester of a fatty acid. Epoxidized oils or corresponding esters can improve the thermal stability and mechanical properties.

[0018] The epoxidized oil can be selected from the group consisting of epoxidized soybean oil, epoxidized castor oil, epoxidized linseed oil, epoxidized palm oil, epoxidized tall oil, and mixtures thereof. Epoxidized soybean oil or epoxidized linseed oil are preferably used in the plasticizer composition according to the invention. Epoxidized soybean oil, also known by the acronym ESBO, is particularly preferred.

[0019] The epoxidized fatty acid esters can be prepared by transesterification of the aforementioned epoxidized oils with alcohols in the range of 1 to 10 carbon atoms, preferably 4 to 9 carbon atoms. Alternatively, the natural oil can first be transesterified and the double bonds of the fatty acid subsequently epoxidized. 202400194

[0020] 4

[0021] The epoxidized oil or the corresponding epoxidized fatty acid alkyl esters may be used in amounts of 1 to 150 parts by weight, based on 100 parts by weight of the total sum of C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid as a compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate. The epoxidized oil or the epoxidized fatty acid esters may also be included in the plasticizer composition in amounts of 2 to 125 parts by weight, 5 to 100 parts by weight, 10 to 80 parts by weight, or 20 to 70 parts by weight, respectively, based on 100 parts by weight of C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid as a compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate.

[0022] The plasticizer composition according to the invention may additionally contain at least one further plasticizer selected from the group consisting of adipates, benzoates, for example monobenzoates or glycol dibenzoates, chlorinated hydrocarbons (so-called chlorinated paraffins), citrates, epoxidized fatty acid esters, epoxidized vegetable oils, epoxidized acylated glycerides, furane dicarboxylates, phosphates, succinates, sulfonamides, sulfonates, terephthalates with the exception of the already existing terephthalates, isophthalates, phthalates, trimellites, cyclohexane dicarboxylates and oligomeric or polymeric esters based on adipic, succinic or sebacic acid.

[0023] In a preferred embodiment of the present invention, the plasticizer composition includes at least one further plasticizer from the group consisting of alkyl benzoates, alkyl sulfonic acid esters of phenol, dialkyl adipates, glycerol esters, C4 to C6 alkanoic acid esters of polyols, acetylated or non-acetylated trialkyl citric acid esters, glycol dibenzoates, trialkyl esters of trimellitic acid, dialkyl terephthalates with the exception of the already existing terephthalates, dialkyl phthalates, dialkyl isophthalates, esters of furandicarboxylic acid, dialkanoyl esters of dianhydrohexitols (e.g. isosorbide), epoxidized fatty acid alkyl esters, polymer plasticizers, for example the polyadipates, dialkyl esters of 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid.

[0024] In a further preferred embodiment, the at least one additional plasticizer that may be included in the plasticizer composition according to the invention is selected from the group consisting of C8 to C13 alkyl benzoates, C4 to C10 dialkyl adipates, pentaerythritol tetravalerate, acetylated or non-acetylated trialkyl citric acid esters with C2 to C9 alkyl groups, C4 to C10 trialkyl trimellites, C6 to C9 dialkyl terephthalates, C4 to C13 dialkyl phthalates, in particular C9 to C13 dialkyl phthalates and C4 to C10 dialkyl esters of 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid.

[0025] Butyl, pentyl, or higher citrates, which may contain an acetyl group, are particularly preferred. These include tributyl citrate, tripentyl citrate, tri-n-hexyl citrate, tri-2-ethylhexyl citrate, triisononyl citrate, acetyltributyl citrate, and acetyltripentyl citrate. Of the C4 to C10 dialkyl adipates, diethylhexyl adipate (DEHA) and diisononyl adipate (DINA) are preferred. Of the C6 to C9 dialkyl terephthalates, diethylhexyl terephthalate (DEHT or DOTP) is preferred.

[0026] 5

[0027] C10 trialkyl trimellites are preferred: triethylhexyl trimellite (TEHTM or TOTM) and triisononylterephthalate (TINTM). Of the C4 to C10 dialkyl esters of 1,4-cyclohexanedicarboxylic acid, 1,4-di-2-ethylhexylcyclohexanedicarboxylic acid ester (1,4-DEHCH) and 1,4-diisononylcyclohexanedicarboxylic acid ester (1,4-DINCH or DINCD) are preferred. Of the C4 to C10 dialkyl esters of 1,2-cyclohexanedicarboxylic acid, 1,2-di-2-ethylhexylcyclohexanedicarboxylic acid ester (1,2-DEHCH) and 1,2-diisononylcyclohexanedicarboxylic acid ester (1,2-DINCH) are preferred.

[0028] A further object of the present invention is a plastic composition comprising a plastic and a plasticizer composition comprising the C4 to C9 alkyl esters of 1,2,4-cyclohexanetripropionic acid as a compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate. The plastic composition may also contain the epoxidized oil and / or an epoxidized fatty acid alkyl ester and / or at least one additional plasticizer from the above-mentioned list.

[0029] Suitable plastics are polymeric substances, preferably from the group consisting of PVC (polyvinyl chloride), homo- or copolymers based on ethylene, propylene, butadiene, vinyl acetate, glycidyl acrylate, glycidyl methacrylate, ethyl acrylate, butyl acrylate or methacrylate with alkoxy groups of branched or unbranched alcohols with one to ten carbon atoms, acrylonitrile or cyclic olefins, polyvinylidene chloride (PVDC), polyacrylates, in particular polymethyl methacrylate (PMMA), polyalkyl methacrylate (PAMA), polyureas, silylated polymers, fluoropolymers, in particular polyvinylidene fluoride (PVDF), polytetrafluoroethylene (PTFE), polyvinyl acetate (PVAc), polyvinyl alcohol (PVA), polyvinyl acetals, in particular polyvinyl butyral (PVB), polystyrene polymers, in particular polystyrene (PS), expandable polystyrene (EPS). Acrylonitrile styrene acrylate (ASA), styrene acrylonitrile (SAN), acrylonitrile butadiene styrene (ABS), styrene maleic anhydride copolymer (SMA),Styrene-methacrylic acid copolymer, polyolefins, in particular polyethylene (PE) or polypropylene (PP), thermoplastic polyolefins (TPO), polyethylene vinyl acetate (EVA), polycarbonates, polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyoxymethylene (POM), polyamide (PA), polyethylene glycol (PEG), polyurethane (PU), thermoplastic polyurethane (TPU), polysulfides (PSu), biopolymers, in particular polylactic acid (PLA), polyhydroxybutyral (PHB), polyhydroxyvaleric acid (PHV), polyesters, starch, cellulose and cellulose derivatives, in particular nitrocellulose (NC), ethylcellulose (EC), cellulose acetate (CA), cellulose acetate / butyrate (CAB), rubber and silicones, may be selected.

[0030] In a preferred embodiment, the plastic in the plasticizer composition is selected from the group consisting of polyvinyl chloride (PVC), polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfides, polylactic acid (PLA), polyhydroxybutyral (PHB), nitrocellulose, and copolymers of vinyl chloride with vinyl acetate or with butyl acrylate. PVC is particularly preferred as the plastic in the plastic composition according to the invention. 202400194

[0031] 6

[0032] The amount of the plasticizer composition according to the invention in the plastic composition is preferably 5 to 150 parts by weight, preferably 10 to 120 parts by weight, particularly preferably 15 to 110 parts by weight and most preferably 20 to 100 parts by weight of the plastic.

[0033] The plastic composition may contain additional additives besides the aforementioned ingredients. Examples of additional additives are rheological additives, which can reduce the viscosity of the plastic composition. Examples of known rheological additives are the products available under the trade names VISCOBYKO-5120, VISCOBYKO-5130, and VISCOBYKO-4041. The additives may be present in a proportion of 1 to 12, preferably 2 to 10 parts by weight per 100 parts by weight of PVC in the plastic composition.

[0034] Furthermore, the plastic composition may contain one or more thermostabilizers. Suitable thermostabilizers include lead salts, organotin compounds, barium / zinc compounds, cadmium or zinc compounds, calcium / zinc stabilizers, and organic-based stabilizers (OBS). Preferred thermostabilizers are barium / zinc compounds, calcium / zinc stabilizers, and organic-based stabilizers (OBS). The proportion of the stabilizer(s) in the plastic composition is preferably 1 to 6 parts by weight per 100 parts by weight of PVC.

[0035] In addition, fillers, pigments, blowing agents and lubricants may also be included in the plastic composition as additives.

[0036] The plastic composition according to the invention is preferably a component of an adhesive, a sealant, a coating compound, a varnish, a paint, a plastisol, a dry blend, a foam, an artificial leather, a floor covering, in particular its top or foam layer, a roofing membrane, an underbody protection, a fabric coating, a cable, a wire insulation, a hose, an extruded article, a film, an object in the automotive interior, a wallpaper, an ink, a toy, a contact film, a food packaging or a medical article, in particular a hose or a blood bag.

[0037] The present invention therefore also relates to the use of the plastic composition in adhesives, sealants, coatings, varnishes, paints, plastisols, foams, artificial leather, floor coverings, in particular top and foam layers, roofing membranes, underbody protection, fabric coatings, cables, wire insulation, hoses, extruded articles, films, in automotive interiors, in wallpaper, inks, toys, contact films, food packaging or medical articles, in particular in hoses or blood bags. 202400194

[0038] 7

[0039] The present invention is illustrated below by means of examples. The following examples are intended to explain the invention without limiting its scope of application as set out in the description and the claims.

[0040] Examples

[0041] Example 1a - Preparation of cyclohexane-1,2,4-tripropionic acid trimethyl ester (Me-Tc)

[0042] [Pd(acac)₂] (15.2 mg, 0.1 mol%), catalyst L (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, MeOH (30 mL) and trivinylcyclohexane (8.1 g, 50 mmol) were injected via syringe. The autoclave was purged three times with CO₂ and subsequently pressurized to 40 bar. The reaction was carried out for 10 h at 110 °C. Afterward, the autoclave was cooled to room temperature and depressurized. The desired product was obtained by distillation (165 °C at 10 -3 bar) cleaned and with 1 H-, 13 Characterized by C-NMR and HR-MS (15.6 g, 91% yield).

[0043] Example 1b - Preparation of cyclohexane-1,2,4-tripropionic acid tripentyl ester (MbPe-Tc)

[0044] The trimethyl ester (Me-Tc) prepared according to Example 1a was transesterified to the product MbPe-Tc in a typical laboratory transesterification apparatus with 2-methylbutanol and n-pentanol (molar ratio 7:93). The transesterification apparatus consists of a glass flask equipped with a stirrer, temperature sensor, distillation column, vacuum divider, and distillation setup. 202400194

[0045] 8

[0046] Initially, 127 g of 2-methylbutanol, 1690 g of n-pentanol, and 1880 g of M-Tc were placed in the transesterification apparatus. The entire apparatus was then purged with nitrogen, and subsequently, 2.72 g of tetra(n-butyl)titanate (TNBT) was added as a catalyst. The reaction was then initiated by heating. The reaction temperature ranged from 130 to 240°C, meaning it increased during the reaction. Methanol produced during the transesterification was removed from the system via the column and distillation apparatus (65°C head temperature). The C5 alcohols, separated from the methanol in the column, were refluxed back into the reaction mixture. When no further distillate was observed, the reaction progress was monitored via GC analysis. The reaction was terminated when the triester accounted for >99% of the GC surface area, based on the sum of the surface areas of the reactant, mono-, di- and triester.

[0047] Following the reaction, the excess alcohol was distilled off under vacuum at 160 °C. The acid number of the reaction mixture was then determined and neutralized by adding three times the stoichiometric amount of 10% NaOH. Next, the mixture was stripped with nitrogen at 160 °C for 2 hours. Finally, the product was filtered clear through a 0.5 dm PTFE filter with perlite as a filter aid.

[0048] Example 1c - Preparation of cyclohexane-1,2,4-tripropionic acid trisononyl ester (In-Tc)

[0049] The trimethyl ester (Me-Tc) prepared according to Example 1a) was transesterified with isononanol to give the product In-Tc in a typical laboratory transesterification apparatus as in Example 1b).

[0050] Initially, 1944 g of isononanol (INA, manufactured by Evonik Oxeno GmbH & Co. KG) and 1230 g of M-Tc were placed in the transesterification apparatus. The entire apparatus was then purged with nitrogen. Next, 2.03 g of tetra(n-butyl)titanate (TNBT) were added as a catalyst. The reaction was then initiated by heating. The reaction temperature was 130–240°C, i.e., it increased during the reaction. Methanol produced during the transesterification was removed from the system via the column and distillation apparatus (65°C head temperature). The INA, separated from the methanol in the column, was refluxed back into the reaction mixture. A slight vacuum was occasionally applied to obtain sufficient distillate. Once no further distillate was observed, the reaction progress was monitored by GC analysis.The reaction was complete when the triester accounted for >99% of the GC surface area, based on the sum of the surface areas of the reactant, mono-, di- and triester.

[0051] Following the reaction, the excess alcohol was distilled off under vacuum at 180 °C. The acid number of the reaction mixture was then determined and neutralized by adding three times the stoichiometric amount of 10% NaOH. Next, the mixture was stripped with nitrogen at 180 °C for 2 hours. Finally, the product was filtered clear through a 0.5 Ω PTFE filter with perlite as a filter aid. 202400194

[0052] 9

[0053] Example 2 - Production of plastisols

[0054] PVC plastisols were produced, such as those used for manufacturing topcoat films for floor coverings. The plastisol formulations are given in parts by weight (phr). The polymer composition formulations are listed in Tables 1 and 2.

[0055] Table 1: Overview of the manufactured plastisols (MbPe-Tc with DBT or DPT).

[0056] * = composition according to the invention phr = parts per hundred parts resin

[0057] 202400194

[0058] 10

[0059] Table 2: Overview of the produced plastisols (In-Tc / Me-Tc).

[0060] * = composition according to the invention

[0061] First, the liquid and then the powdered components were weighed into a PE beaker. The mixture was stirred by hand with a spatula until no unwetted powder remained. The sealed beaker was placed in the holder in the speed mixer, mixed, and vented. After mixing was complete, the temperature of the plastisol was measured using an IR thermometer. The plastisol was then immediately tempered at 25.0 °C in a climate chamber for further analysis.

[0062] Example 3 - Gelation of plastisols

[0063] The gelling behavior of the plastisols from Example 2 was investigated using a Physica MCR 101 in oscillation mode with a plate-plate measuring system (PP25) operated under shear stress control. An additional temperature control hood was connected to the instrument to achieve homogeneous heat distribution and a uniform sample temperature.

[0064] 202400194

[0065] 11

[0066] The following parameters were set:

[0067] Mode: Temperature gradient

[0068] Starting temperature: 25 °C

[0069] Final temperature: 180 °C

[0070] Heating / cooling rate: 5 °C / min

[0071] Oscillation frequency: 4 to 0.1 Hz, logarithmic ramp

[0072] Omega angular frequency: 10 s 1

[0073] Number of measuring points: 63

[0074] Measurement duration: 0.5 min

[0075] Automatic gap tracking F 0 N

[0076] Constant measurement point duration

[0077] Gap width 0.5 mm

[0078] Performing the measurement

[0079] A few grams of the paste to be measured were applied to the lower measuring system plate using a spatula, ensuring no air bubbles were present. Care was taken to allow some paste to ooze out evenly from the measuring system after it was closed (no more than 6 mm all around). The excess was removed with a spatula. The temperature control hood was then positioned over the sample and the measurement started. The complex viscosity of the paste was determined after 24 hours (storage of the paste at 25 °C in a temperature control chamber from Memmert) as a function of temperature.

[0080] A significant increase in complex viscosity was considered a measure of gelation. Therefore, the temperature at which a paste viscosity of 1000 Pa*s was reached was used as a reference value. The results obtained are listed in Table 3.

[0081] Table 3: Gelation of the plastisols after 24 hours, temperature in °C at reaching a paste viscosity of 1000 Pa*s.

[0082] * Test with plasticizer composition according to the invention 202400194

[0083] 12

[0084] The addition of DBT or DPT to C4 to C9 esters of 1,2,4-cyclohexanetricarboxylic acid results in a significantly accelerated gelation compared to C4 to C9 esters of 1,2,4-cyclohexanetricarboxylic acid without additional plasticizer.

[0085] Example 4 - Measurement of plastisolviscosities

[0086] The viscosity of the plastisols produced in Example 2 was measured using a Physica MCR 101 rheometer (Anton Paar Germany GmbH) with the help of the associated software, using the rotation mode and the CC27 measuring system.

[0087] The following points were targeted during the measurement:

[0088] Pre-shear at 100 s-1 for a period of 60 seconds, during which no measurements were recorded.

[0089] Shear rate down-ramp from 200 s⁻¹ to 0.1 s⁻¹. 30 measurement points were recorded with a measurement duration of 10 seconds each.

[0090] The measurements were performed at room temperature. The results of the viscosity measurements of the plastisols produced in Example 2 with the respective plasticizers or plasticizer mixtures are shown in Table 4.

[0091] Table 4: Plastisolviosities and glass transition temperatures a: Measurement at shear rates > 137 s 1 Aborted due to high viscosity.

[0092] The addition of DBT or DPT to C4 to C9 esters of 1,2,4-cyclohexanetricarboxylic acid significantly reduces the paste viscosity compared to C4 to C9 esters of 1,2,4-cyclohexanetricarboxylic acid without additional plasticizer. Furthermore, the glass transition temperature is lowered by the addition of DBT and DPT.

Claims

202400194 13 Patent claims 1. Plasticizer composition containing a compound of formula (1) wherein the three alkyl groups R each have 4 to 9 carbon atoms, and dibutyl terephthalate or dipentyl terephthalate.

2. Plasticizer composition according to claim 1, wherein the three alkyl groups R are each selected independently of one another from the group consisting of a normal butyl group, an isobutyl group, a normal pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a normal hexyl group, an isohexyl group, a normal heptyl group, an isoheptyl group, a normal octyl group, an isooctyl group, a normal nonyl group or an isononyl group.

3. Plasticizer composition according to claim 1 or 2, wherein the three alkyl groups R of the compound according to formula (1) have the same number of carbon atoms.

4. Plasticizer composition according to any of the preceding claims, wherein the compound according to formula (1) is a tripentyl ester of 1,2,4-cyclohexanetripropionic acid or a triisonony ester of 1,2,4-cyclohexanetripropionic acid.

5. Plasticizer composition according to one of the preceding claims, wherein the compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate are present in the plasticizer composition in a weight ratio (compound according to formula (1) : dibutyl terephthalate or dipentyl terephthalate) of 1 : 99 to 99 : 1, preferably 10 : 90 to 90 : 10, particularly preferably 30 : 70 to 70 :

30.

6. Plasticizer composition according to any of the preceding claims, wherein the plasticizer composition additionally comprises an epoxidized oil or an epoxidized alkyl ester of a fatty acid.

7. Plasticizer composition according to claim 6, wherein the epoxidized oil is from the group consisting of epoxidized soybean oil, epoxidized castor oil, epoxidized linseed oil, 202400194 14 epoxidized palm oil, epoxidized stearate, epoxidized oleate, epoxidized tallol, epoxidized linoleate and mixtures thereof are selected.

8. Plasticizer composition according to claim 7, wherein the epoxidized oil is epoxidized soybean oil or epoxidized linseed oil, preferably epoxidized soybean oil.

9. Plasticizer composition according to any one of claims 6 to 8, wherein the epoxidized oil is present in an amount of 1 to 150 parts by weight based on 100 parts by weight of the total sum of the compound according to formula (1) and dibutyl terephthalate or dipentyl terephthalate in the plasticizer composition.

10. Plasticizer composition according to one of the preceding claims, wherein the composition further comprises a further plasticizer selected from the group consisting of adipates, benzoates, for example monobenzoates or glycol dibenzoates, chlorinated hydrocarbons (so-called chlorinated paraffins), citrates, epoxidized fatty acid esters, epoxidized vegetable oils, epoxidized acylated glycerides, furane dicarboxylates, phosphates, succinates, sulfonamides, sulfonates, terephthalates with the exception of dibutyl terephthalate or dipentyl terephthalate, isophthalates, trimellites, cyclohexane dicarboxylates and oligomeric or polymeric esters based on adipic, succinic or sebacic acid.

11. Plastic composition comprising the plasticizer composition according to any one of claims 1 to 10 and a plastic.

12. Plastic composition according to claim 11, wherein the proportion of the plasticizer composition is 5 to 150 parts by weight per 100 parts by weight of plastic.

13. Plastic composition according to claim 11 or 12, wherein the plastic is selected from the group consisting of polyvinyl chloride (PVC), polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfides, polylactic acid (PLA), polyhydroxybutyral (PHB), nitrocellulose and copolymers of vinyl chloride with vinyl acetate or with butyl acrylate.

14. Plastic composition according to claim 13, wherein the plastic is polyvinyl chloride (PVC).

15. Use of the plastic composition according to any one of claims 11 to 14 in adhesives, sealants, coatings, varnishes, paints, plastisols, foams, artificial leather, floor coverings, in particular top and foam layers, roofing membranes, underbody protection, fabric coatings, cables, wire insulation, hoses, extruded articles, films, in automotive interiors, in wallpapers, inks, toys, contact films, food packaging or medical articles, in particular in hoses or blood bags.

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