Plasticizer composition containing trimethyl ester of 1,2,4-cyclohexanetripropionic acid and dialkylphthalic acid ester

Abstract

The invention relates to a plasticizer composition containing a compound of formula (1) and at least one dialkylphthalic acid ester, wherein each of the two alkyl groups in the dialkylphthalic acid ester has 9 or 10 carbon atoms.

Description

[0001] 202400052

[0002] 1

[0003] Plasticizer composition containing trimethyl esters of 1,2,4-cyclohexanetripropionic acid and dialkylphthalic acid esters

[0004] The invention relates to a plasticizer composition containing a compound of formula (1) and at least one dialkylphthalic acid ester, wherein the two alkyl groups in the dialkylphthalic acid ester each have 9 or 10 carbon atoms.

[0005] The compounds according to formula (1) of the invention are trimethyl esters of 1,2,4-cyclohexanetripropionic acid. Trimethyl esters of 1,2,4-cyclohexanetripropionic acid are generally known and have been described, for example, in EP 3 838 886 A1. It was also mentioned there that these esters of 1,2,4-cyclohexanetripropionic acid can be used as plasticizers. In this context, the trimethyl ester was described as a product with a low gelling temperature.

[0006] The most important types of plasticizers, at least in Europe and North America, are still the dialkyl phthalates, and in particular those with 9 or 10 carbon atoms in the alkyl groups. These include the phthalic acid esters, which are produced from the alcohols or alcohol mixtures isononanol (a mixture of linear and branched, primary C9 alcohols), n-nonanol, n-decanol, 2-propylheptanol, and isodecanol (a mixture of primary, predominantly branched primary C10 alcohols, which may optionally also contain C9 and / or C11 alcohols).

[0007] Esters of the branched alcohols / alcohol mixtures isononanol, isodecanol, and 2-propylheptanol, namely diisononyl phthalate (DINP), diisodecyl phthalate (DIDP), and dipropylheptyl phthalate (DPHP), are particularly preferred as plasticizers. The latter three, in particular, are considered "general-purpose" plasticizers, suitable for most applications.

[0008] In plastisol applications, these plasticizers are often combined with other plasticizers with lower processing temperatures, so-called rapid gelling agents, to increase processing speed. Common rapid gelling agents include glycol dibenzoates, C8-C10 monobenzoates, and also dibutyl or dipentyl terephthalates. However, these also show 202400052

[0009] 2

[0010] Some systems, especially in combination with phthalates, still have certain application-related deficiencies.

[0011] This leads to the need to find new rapid gelling agents that can be used together with the dialkyl phthalates and exhibit improved properties compared to the state of the art.

[0012] The present invention was based on the objective of providing a plasticizer composition containing the trimethyl ester of 1,2,4-cyclohexanetripropionic acid, but exhibiting better application-related properties than plasticizer compositions with other rapid gelling agents.

[0013] 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) and at least one dialkylphthalic acid ester, wherein the two alkyl groups each have 9 or 10 carbon atoms. Preferred embodiments of the present invention are specified in the dependent claims.

[0014] The trimethyl ester of 1,2,4-cyclohexanetripropionic acid, i.e., the substance that constitutes part of the plasticizer composition according to the invention, is not currently commercially available. However, a process for the preparation of these esters is described, for example, in EP 3 842411 A1. The esters of 1,2,4-cyclohexanetripropionic acid are therefore generally accessible.

[0015] The three methyl groups present could also have been incorporated into the molecule, either wholly or partially, through the use of biomethanol during synthesis. This would then result in a partially bio-based compound.

[0016] In addition to the trimethyl esters of 1,2,4-cyclohexanetripropionic acid, the plasticizer composition according to the invention contains dialkylphthalic acid esters, wherein the two alkyl groups each have 9 or 10 carbon atoms independently of one another. The dialkylphthalic acid esters are also known as phthalates. The corresponding compounds can be described by the following Markush formula: 202400052

[0017] 3 where the two R groups are each independently alkyl groups with 9 or 10 carbon atoms.

[0018] The two alkyl groups can each be selected independently from the group consisting of a normal nonyl group, an isononyl group, a normal decyl group, an isodecyl group (which may optionally also contain isononyl and isodecyl moieties), and a 2-propylheptyl group. For the purposes of this invention, an isononyl group is understood to be a mixture of linear and branched C9 alcohols.

[0019] In a preferred embodiment of the present invention, the two alkyl groups of the dialkylphthalic acid ester each have the same number of carbon atoms. This means that both alkyl groups have 9 or both alkyl groups have 10 carbon atoms, but not that both alkyl groups must always be identical.

[0020] However, it is particularly preferred that the dialkyl phthalic acid ester in the composition according to the invention is di-isononyl phthalic acid ester (DINP) or di-2-propylheptyl phthalic acid ester (DPHP). DINP is most preferably used as the dialkyl phthalic acid ester.

[0021] The dialkylphthalic acid esters according to the invention can be prepared by direct esterification of phthalic acid or the corresponding anhydride with an alcohol having 9 or 10 carbon atoms. The alcohol is preferably used in excess, i.e., in an amount of more than 2 moles per mole of acid component. The direct esterification is further preferably carried out over an acidic catalyst, for example, inorganic, organic, or Lewis acids.

[0022] The dialkylphthalic acid esters according to the invention can also be produced by transesterification, wherein dialkylphthalic acid esters with alkyl groups having fewer than 9 carbon atoms are used and transesterified with an alcohol having 9 or 10 carbon atoms. Here too, the alcohol with 9 or 10 carbon atoms can be used in excess.

[0023] Preferably, however, the preparation is carried out via the esterification of phthalic acid, particularly preferably with phthalic anhydride and an alcohol having 9 or 10 carbon atoms. 202400052

[0024] 4

[0025] The two substances can be present in different 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 compound according to formula (1) and the dialkylphthalic acid ester are present in the plasticizer composition in a weight ratio (compound according to formula (1) : dialkylphthalic acid ester) of 1 : 99 to 99 : 1, preferably 10 : 90 to 90 : 10, and particularly preferably 30 : 70 to 70 : 30. In a most preferred embodiment of the present invention, the compound according to formula (1) and the dialkylphthalic acid ester are present in the plasticizer composition in a weight ratio (compound according to formula (1) : dialkylphthalic acid ester) of 30 : 70 to 5 : 95.

[0026] The plasticizer composition according to the present invention may 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.

[0027] 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.

[0028] 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.

[0029] The epoxidized oil or the corresponding epoxidized fatty acid alkyl esters may be used in amounts of 1 to 150 parts by weight per 100 parts by weight of the total sum of the compound according to formula (1) and the dialkylphthalic acid ester. 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, each based on 100 parts by weight of the total sum of the compound according to formula (1) and the dialkylphthalic acid ester.

[0030] The plasticizer composition according to the invention may additionally contain at least one further plasticizer 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, phthalates with the exception of the already existing esters with 9 or 10 carbon atoms, terephthalates, isophthalates, phthalates 202400052

[0031] 5 with the exception of the already existing esters, trimellites, cyclohexanedicarboxylates and oligomeric or polymeric esters based on adipic, succinic or sebacic acid.

[0032] In a preferred embodiment of the present invention, the plasticizer composition comprises 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, dialkyl phthalates with the exception of the already existing esters with 9 or 10 carbon atoms, dialkyl isophthalates, esters of furandicarboxylic acid, dialkanoyl esters of dianhydrohexitols (e.g. isosorbide), epoxidized fatty acid alkyl esters, polymer plasticizers, for example the polyadipates and dialkyl esters of 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid.

[0033] 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, C4 to C9 dialkyl terephthalates, C4 to C13 dialkyl phthalates, with the exception of the already existing esters with 9 or 10 carbon atoms and C4 to C10 dialkyl esters of 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid.

[0034] 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 C4 to C9 dialkyl terephthalates, dibutyl terephthalate (DBT), dipentyl terephthalate (DPT), and diethylhexyl terephthalate (DEHT or DOTP) are preferred. Of the C4 to C10 trialkyl trimellites, triethylhexyl trimellite (TEHTM or TOTM) and triisononyl terephthalate (TINTM) are preferred. Of the C4 to C10 dialkyl esters of 1,4-cyclohexanedicarboxylic acid, the 1,4-diethylhexylcyclohexanedicarboxylic acid ester (1,4-DEHCH) and the 1,4-diisononylcyclohexanedicarboxylic acid ester (1,4-DINCH or DINCD) are preferred.Of the C4 to C10 dialkyl esters of 1,2-cyclohexanedicarboxylic acid, the 1,2-diethylhexylcyclohexanedicarboxylic acid ester (DEHCH) and the 1,2-diisononylcyclohexanedicarboxylic acid ester (DINCH) are preferred.

[0035] Another object of the present invention is a plastic composition comprising a plastic and the plasticizer composition comprising the compound of formula (1) and at least one dialkylphthalic acid ester, wherein the two alkyl groups each have 9 or 10 carbon atoms. The plastic composition may also include the epoxidized oil and / or an epoxidized fatty acid alkyl ester and / or at least one additional plasticizer from the above list. 202400052

[0036] 6

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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 202400052

[0042] 7

[0043] Barium / zinc compounds, calcium / zinc stabilizers, and organic-based stabilizers (so-called 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.

[0044] In addition, fillers, pigments, blowing agents and lubricants may also be included in the plastic composition as additives.

[0045] 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.

[0046] 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 wallpapers, inks, toys, contact films, food packaging or medical articles, in particular in hoses or blood bags.

[0047] 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.

[0048] Examples

[0049] Example 1 - Preparation of cyclohexane-1,2,4-tripropionic acid trimethyl ester (Me-Tc) 202400052

[0050] 8

[0051] [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).

[0052] Example 2 - Production of plastisols

[0053] PVC plastisols were produced, such as those used in the manufacture of topcoat films for floor coverings. The plastisol formulations are given in parts by weight (phr). The polymer composition is listed in Tables 1 and 2.

[0054] 202400052

[0055] 9

[0056] Table 1: Overview of the produced plastisols (Part 1)

[0057] * = composition according to the invention phr = parts per hundred parts resin

[0058] 202400052

[0059] 10

[0060] Table 2: Overview of the produced plastisols (Part 2)

[0061] * = composition according to the invention phr = parts per hundred parts resin

[0062] 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.

[0063] Example 3 - Production of films

[0064] The plastisols produced in Example 2 were each processed into 1 mm thick films. First, high-gloss release paper (Sappi, Italy) was cut to a size of 30 x 44 cm and placed in the tensioning frame of the LTSV coating unit for the Mathis oven. The tensioning frame was then placed on the guide frame, the Mathis oven (type LTF) was set to 200 °C, and the frame was preheated for 15 seconds after reaching this temperature. Next, the doctor blade was placed in the clamping device, and the blade gap was adjusted through preliminary tests so that the film thickness after gelation was 1 mm (+ / - 0.05 mm). An adhesive strip was applied to the leading edge of the paper to catch excess plastisol. The plastisol was then placed in front of the 202400052

[0065] 11

[0066] The plastisol was applied with a squeegee and spread across the clamped release paper by pulling the guide frame with the squeegee (3 m / min speed). The squeegee was then removed and the adhesive strip with the excess plastisol was wiped away. The frame was then placed in the oven. After gelation (2 minutes at 200 °C), the frame was removed from the oven and, after cooling, the film was peeled off the paper.

[0067] Example 4 - Determination of mass loss (activated carbon method)

[0068] Following DIN EN ISO 176 (Method B), three circular discs with a diameter of 5 cm were punched out from the manufactured PVC films and initially conditioned for 16 hours in a desiccator at room temperature. The sample discs were weighed on an analytical balance, placed in a wire basket, and closed with a clamp. The wire baskets were then placed in a tin can filled with activated carbon, ensuring that there was approximately 130 ml of activated carbon between each basket, between the basket and the lid (perforated), and between the can and the base.

[0069] The filled tin cans were placed in a pre-heated oven (120 °C) in such a way that the fan was not obstructed and the cans did not touch each other. Air exchange and exhaust damper were each set to 10%. After 72 hours, the cans were removed from the oven, cooled, and then the individual samples were taken from the baskets, conditioned for another 16 hours in a desiccator, and then weighed again on an analytical balance. The resulting mass difference is due to the loss of plasticizer. The average of the three mass differences was calculated, and the percentage loss of plasticizer was determined. The results are shown in Table 3.

[0070] Table 3: Mass loss of the test specimens

[0071] * = composition according to the invention 202400052

[0072] 12

[0073] The mass loss of films with the plasticizer composition according to the invention is lower than that of films produced with plasticizer compositions containing other rapid gelling agents. Comparing the mass losses of mixtures 1, 4 and 5 as well as 8 and 11, one surprisingly observes only a slight increase in mass loss despite significantly increasing proportions of the rapid gelling agent Me-Tc.

[0074] Example 5 - Determining migration characteristics

[0075] The test for determining the migration properties of a test specimen containing the plasticizer compositions under test allows conclusions to be drawn about how plasticizer-containing polymer bodies behave in application when in direct contact with other materials – such as contact between a plasticized PVC layer and a polystyrene layer (so-called "multi-layer systems"). For example, if plasticizer migrates from a plasticized polymer-containing component to a non-plasticized polymer-containing component within an article, this can lead to undesirable embrittlement of the plasticized component and softening of the non-plasticized component, which can result in leaks, reduced stability, and a shortened service life of the article.Accordingly, a low migration tendency is an important property for a plasticizer that can be used in numerous applications or for a corresponding component of a plasticizer composition.

[0076] The migration tendency of the above-mentioned plasticizer compositions was determined as follows:

[0077] The 1 mm thick films produced according to Example 4 were cut into test pieces of 100 mm x 100 mm and stored for 24 hours at 23 °C before their mass was determined using an analytical balance.

[0078] Following the standard DIN EN ISO 177 (published in 1999), the test specimens were placed between two contact layers (high-impact polystyrene (HIPS), manufactured by VINK Kunststoffe; 100 x 100 x 2 mm sheets), which had the same dimensions as the test specimens except for a thickness of 2 mm. Two of these layered structures were then stacked on top of each other. These stacks, each containing test specimens with the same plasticizer, were weighted down with a 2 kg weight and stored in an oven (70 (+ / - 1) °C) for 28 days.

[0079] After 14 days and after 28 days, the weight loss of each specimen was determined (percentage weight loss based on the original weight). After the first measurement, the stacks were reassembled as before. Table 4 shows the average weight loss values ​​of the specimens. 202400052

[0080] 13

[0081] Table 4: Migration into high-impact polystyrene (HIPS) after 14 and 28 days respectively

[0082] * = composition according to the invention

[0083] It can be seen that the plasticizer compositions according to the invention have an equivalent or lower migration tendency than plasticizer compositions containing other rapid gelling agents.

[0084] Example 6 - Efficiency of plasticizer absorption based on Shore A hardness determination: 4.8 x 4.8 cm sheets were produced from the films manufactured according to Example 4. 2Large pieces were cut. These were stacked in a press frame in 6 to 8 layers, depending on the film thickness, and pressed at 170 °C and 200 bar. The test specimens were then conditioned for at least 16 hours in a climate chamber under standard climate conditions and subsequently measured using a Shore A measuring device from Zwick-Roell, in accordance with DIN 48-4 (2021-02). The measured values ​​were read after 3 seconds. Measurements were taken at three different points on each test specimen, and the average value was calculated. The results are listed in Table 5. 202400052

[0085] 14

[0086] Table 5: Shore hardness

[0087] * = composition according to the invention

[0088] The same amount of the plasticizer compound was added to all test specimens. However, the lowest hardness was only observed in the test specimens treated with the plasticizer compound according to the invention.

[0089] Plasticizer composition. It is found that the plasticizer compositions 1, 4, 5, 8 and 11 according to the invention exhibit a better or at least equally good plasticizer absorption efficiency.

Claims

202400052 15 Patent claims 1. Plasticizer composition containing a compound of formula (1) and at least one dialkylphthalic acid ester, wherein the two alkyl groups each have 9 or 10 carbon atoms.

2. Plasticizer composition according to claim 1, wherein the two alkyl groups are each selected independently of one another from the group consisting of a normal nonyl group, an isononyl group, a normal decyl group and a 2-propylheptyl group.

3. Plasticizer composition according to claim 1 or 2, wherein the two alkyl groups have the same number of carbon atoms.

4. Plasticizer composition according to any of the preceding claims, wherein the dialkyl phthalic acid ester is di-isononyl phthalic acid ester (DI NP) or di-2-propylheptyl phthalic acid ester (DPHP).

5. Plasticizer composition according to one of the preceding claims, wherein the compound according to formula (1) and the dialkylphthalic acid ester are present in the plasticizer composition in a weight ratio (compound according to formula (1) : dialkylphthalic acid ester) 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 selected from the group consisting of epoxidized soybean oil, epoxidized castor oil, epoxidized linseed oil, epoxidized palm oil, epoxidized stearate, epoxidized oleate, epoxidized tall oil, epoxidized linoleate and mixtures thereof. 202400052 16 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 the plasticizer composition 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 the dialkylphthalic acid ester.

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, isophthalates, phthalates, with the exception of the already existing esters with 9 or 10 carbon atoms, 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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