Plasticizer composition and resin composition

Abstract

The present invention relates to a plasticizer composition and a resin composition comprising the plasticizer composition, the plasticizer composition comprising: a pyromellitate compound represented by chemical formula 1; and a trimellitate compound represented by chemical formula 2 or a terephthalate compound represented by chemical formula 3, wherein the total amount of the compound represented by chemical formula 2 or 3 is 20 wt% or less on the basis of the total weight of the plasticizer composition.

Description

Plasticizer composition and resin composition

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority based on Korean patent applications No. 10-2025-0022937 and No. 10-2025-0022938 dated February 21, 2025, and all contents disclosed in the documents of said Korean patent applications are incorporated herein as part of this specification.

[0003] Technology field

[0004] The present invention relates to a plasticizer composition and a resin composition comprising a pyromellitate compound and a trimellitate or terephthalate compound together.

[0005] Plasticizers are generally esters produced by the reaction of polycarboxylic acids, such as phthalic acid and adipic acid, with alcohols, and are primarily added to resins such as PVC to impart flexibility and mechanical properties. Although traditionally used phthalate-based plasticizers possess excellent plasticizing performance, they are subject to domestic and international regulations due to concerns that they may be harmful to the human body. Consequently, research on phthalate-based alternative plasticizers, such as terephthalate-based, adipate-based, and polymer-based alternatives, is actively underway, and the demand for eco-friendly alternative materials is increasing.

[0006] Recently, environmental requirements for products using plasticizers have been becoming increasingly stringent in various industries, such as wires, cables, flooring, wallpaper, and soft and rigid sheets. In these sectors, it is crucial to select suitable additives by considering physical properties such as tensile strength, elongation, heating loss, light resistance, migration, and plasticization rate, in order to improve the quality, processability, and productivity of finished products.

[0007] In particular, di(2-ethylhexyl) terephthalate (DEHTP), one of the most widely used plasticizers, is inexpensive and highly versatile, but it has the disadvantages of high heat loss and poor migration. Although various studies are being conducted to address these issues, existing plasticizers require improvements in thermal stability, plasticization efficiency, and mechanical properties.

[0008] Therefore, to develop eco-friendly products, it is necessary to develop new plasticizer compositions that can replace phthalate-based plasticizers. In particular, industries requiring high heat resistance and low heat loss, such as electric vehicles, demand high-performance, eco-friendly plasticizers to replace existing ones, and innovative research to address this is ongoing.

[0009] The present invention is capable of solving the above problem by providing a novel plasticizer composition and a resin composition containing the same, which can achieve improvement in some properties while maintaining some of the various properties required of existing plasticizers at an equivalent level by including a pyromellitate compound together with trimellitate or terephthalate.

[0010] To solve the above-mentioned problems, the present invention provides a plasticizer composition and a resin composition.

[0011] More specifically, (1) the present invention provides a plasticizer composition comprising a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2 or 3, wherein the total content of the compound represented by chemical formula 2 or 3 based on the total weight of the plasticizer composition is 20 weight% or less:

[0012] [Chemical Formula 1]

[0013]

[0014] [Chemical Formula 2]

[0015]

[0016] [Chemical Formula 3]

[0017]

[0018] In the above formula,

[0019] R1 to R9 are each independently an alkyl group having 8 or 9 carbon atoms.

[0020] (2) The present invention provides a plasticizer composition in which the compound represented by the chemical formula 1 is included in an amount of 70% or more based on the total weight of the plasticizer composition, in accordance with (1).

[0021] (3) The present invention provides a plasticizer composition in which, in (1) or (2), the total content of the compound represented by Formula 2 or 3 based on the total weight of the plasticizer composition is 0.1% by weight or more and 15% by weight or less.

[0022] (4) The present invention provides a plasticizer composition in which, in any one of (1) to (3), R1 to R4 are each independently an alkyl group having 8 carbon atoms.

[0023] (5) The present invention provides a plasticizer composition in which, in any one of (1) to (4), R1 to R4 are 2-ethylhexyl groups.

[0024] (6) The present invention provides a plasticizer composition in which, in any one of (1) to (5), R5 to R7 are each independently an alkyl group having 8 carbon atoms.

[0025] (7) The present invention provides a plasticizer composition in which, in any one of (1) to (6), R5 to R7 is a 2-ethylhexyl group.

[0026] (8) The present invention provides a plasticizer composition in which, in any one of (1) to (7), R8 and R9 are each independently an alkyl group having 8 carbon atoms.

[0027] (9) The present invention provides a plasticizer composition in which, in any one of (1) to (8), R8 and R9 are 2-ethylhexyl groups.

[0028] (10) The present invention provides a plasticizer composition in which, in any one of (1) to (9), R1 to R9 are identical to each other.

[0029] (11) The present invention provides a resin composition comprising a thermoplastic resin and a plasticizer composition according to any one of (1) to (10).

[0030] (12) The present invention provides a resin composition according to (11), wherein the plasticizer composition is included in an amount of 5 parts by weight or more and 150 parts by weight or less per 100 parts by weight of the thermoplastic resin.

[0031] (13) The present invention provides a resin composition in which, in (11) or (12), the resin is one or more selected from the group consisting of ethylene vinyl acetate, polyethylene, polyketone, polypropylene, polyvinyl chloride, polystyrene, polyurethane and thermoplastic elastomer.

[0032] The plasticizer composition according to the present invention can maintain and improve plasticization efficiency and migration resistance to a level equivalent to or greater than that of conventional plasticizers, and in particular, it has excellent aging resistance, oil resistance, and insulation properties, so it can be applied to various wire industries requiring high-quality heat-resistant materials.

[0033] The present invention will be described in more detail below.

[0034]

[0035] Terms and words used in this specification and claims should not be interpreted as being limited to their ordinary or dictionary meanings, but should be interpreted in a meaning and concept consistent with the technical spirit of the invention, based on the principle that the inventor can appropriately define the concept of the terms to best describe his invention.

[0036]

[0037] Definition of Terms

[0038] The term “composition” as used herein includes reaction products and decomposition products formed from the materials of said composition, as well as mixtures of materials comprising said composition.

[0039] In this specification, "alkyl group" means a straight-chain or branched saturated hydrocarbon group.

[0040] The terms “comprising,” “having,” and their derivatives are not intended to exclude the presence of any additional components, steps, or procedures, whether specifically disclosed or not. To avoid any uncertainty, any composition claimed through the use of the term “comprising,” may include any additional additives, adjuvants, or compounds, whether polymers or otherwise, unless otherwise stated. In contrast, the term “essentially composed of” excludes any other components, steps, or procedures from the scope of any subsequent description, except those not essential to operability. The term “composed of” excludes any components, steps, or procedures that are not specifically described or enumerated.

[0041]

[0042] measurement method

[0043] In this specification, 'hardness' refers to Shore hardness (Shore "A" and / or Shore "D") at 25°C using ASTM D2240, measured under conditions of 3T 10s, and can be an indicator for evaluating plasticization efficiency, and a lower value indicates better plasticization efficiency.

[0044] In this specification, 'tensile strength' is calculated by the ASTM D638 method using a test device, a UTM (manufacturer: Instron, model name: 4466), by pulling at a crosshead speed of 200 mm / min (1T), measuring the point where the specimen breaks, and using the following Equation 1.

[0045] [Mathematical Formula 1]

[0046] Tensile strength (kgf / cm²) 2 ) = Load (kgf) / Thickness (cm) x Width (cm)

[0047] In this specification, the 'elongation rate' is calculated by the ASTM D638 method, by using the UTM to pull the crosshead speed at 200 mm / min (1T), measuring the point where the specimen is cut, and then calculating it using the following mathematical formula 2.

[0048] [Mathematical Formula 2]

[0049] Elongation (%) = Length after elongation / Initial length x 100

[0050] In this specification, 'migration loss' refers to obtaining a test specimen with a thickness of 1 mm in accordance with KSM-3156, attaching tracing paper to both sides of the test specimen, and then 2 kgf / cm² 2A load is applied. After leaving the test specimen in a hot air circulating oven (80°C) for 3 days, it is removed and cooled at room temperature for 4 hours. Then, the oil paper attached to both sides of the test specimen is removed, and the weight of the specimen before and after the experiment is measured to calculate the amount of transfer loss using the following mathematical formula 3.

[0051] [Mathematical Formula 3]

[0052] Transfer loss (%) = {(Initial weight of specimen at room temperature - Weight of specimen after oven storage) / Initial weight of specimen at room temperature} x 100

[0053] In this specification, 'volatile loss' refers to measuring the change in weight of a specimen before and after testing, after maintaining the specimen in a gear oven at a specific temperature for a certain period.

[0054] [Mathematical Formula 4]

[0055] Heat Loss (Weight%) = {(Initial Specimen Weight - Specimen Weight After Processing) / Initial Specimen Weight} x 100

[0056] In the case of the various measurement conditions mentioned above, detailed conditions such as temperature, rotational speed, and time may vary slightly depending on the situation, and if they differ, the measurement method and conditions are specified separately.

[0057]

[0058] Plasticizer composition

[0059] The present invention provides a plasticizer composition comprising a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2 or 3, wherein the total content of the compound represented by chemical formula 2 or 3 based on the total weight of the plasticizer composition is 20 weight% or less.

[0060] [Chemical Formula 1]

[0061]

[0062] [Chemical Formula 2]

[0063]

[0064] [Chemical Formula 3]

[0065]

[0066] In the above formula,

[0067] R1 to R9 are each independently an alkyl group having 8 or 9 carbon atoms.

[0068]

[0069] The plasticizer composition of the present invention comprises a pyromellitate compound represented by Formula 1, thereby providing improved physical properties compared to existing commercial plasticizers while maintaining a balance among various physical properties. The alkyl groups R1 to R4 of the compound represented by Formula 1 may be alkyl groups having 8 or 9 carbon atoms. The alkyl group having 8 carbon atoms may be an n-octyl group, a 2-octyl group, a 2-ethylhexyl group, or a tert-octyl group, and the alkyl group having 9 carbon atoms may be an n-nonyl group, a 2-nonyl group, an isononyl group, or a 3,5,5-trimethylhexyl group. More preferably, R1 to R4 may be alkyl groups having 8 carbon atoms, and all may be 2-ethylhexyl groups. When the number of carbon atoms in the alkyl groups of the pyromellitate is 8 or 9, the balance among various physical properties required for the plasticizer composition may be excellent.

[0070]

[0071] The plasticizer composition of the present invention may include a trimellitate compound represented by Formula 2 or a terephthalate compound represented by Formula 3. The plasticizer composition of the present invention may include only one of the trimellitate compound and the terephthalate compound, or both. The substituents R5 to R9 of the trimellitate compound and the terephthalate compound may also be alkyl groups having 8 or 9 carbon atoms, and the alkyl group having 8 carbon atoms may be an n-octyl group, a 2-octyl group, a 2-ethylhexyl group, or a tert-octyl group, and the alkyl group having 9 carbon atoms may be an n-nonyl group, a 2-nonyl group, an isononyl group, or a 3,5,5-trimethylhexyl group. More preferably, R5 to R9 may be alkyl groups having 8 carbon atoms, and all may be 2-ethylhexyl groups. When the alkyl group of the trimellitate and terephthalate has 8 or 9 carbon atoms, compatibility with the previously described pyromellitate can be improved.

[0072]

[0073] The total content of the compound represented by Chemical Formula 2 and / or the compound represented by Chemical Formula 3 in the plasticizer composition may be 20 wt% or less. More specifically, the total content of the trimellitate compound and the terephthalate compound in the plasticizer composition may be 0.01 wt% or more, 0.05 wt% or more, 0.1 wt% or more, 0.5 wt% or more, 1 wt% or more, 2 wt% or more, 3 wt% or more, 4 wt% or more, or 5 wt% or more, and 20 wt% or less, 19 wt% or less, 18 wt% or less, 17 wt% or less, 16 wt% or less, or 15 wt% or less. Meanwhile, the above content may refer to the content of the compound when either the trimellitate compound or the terephthalate compound is included, or the combined content of the two compounds when both compounds are included. When the above content conditions are satisfied, aging resistance, oil resistance, and insulation properties may be further improved.

[0074]

[0075] The compound represented by Chemical Formula 1 above may be 70% by weight or more based on the weight of the total plasticizer composition, and more specifically, 70% by weight or more, 75% by weight or more, 80% by weight or more, 85% by weight or more, or 90% by weight or more, and 99.9% by weight or less, 99.5% by weight or less, 99% by weight or less, 98% by weight or less, 97% by weight or less, 96% by weight or less, or 95% by weight or less. The compound represented by Chemical Formula 1 above is a compound that performs the most important function in the plasticizer composition of the present invention, and when included within the above-described range, the overall physical properties of the plasticizer composition are excellent, and a balance between them can be maintained.

[0076]

[0077] In the compounds represented by the above chemical formulas 1 to 3, it may be preferable that R1 to R9 are all identical to each other. If R1 to R9 are identical to each other, the compatibility between the compounds is improved, and the physical properties of the overall plasticizer composition can be improved.

[0078]

[0079] Resin composition

[0080] The present invention can provide a resin composition comprising a thermoplastic resin and a plasticizer composition.

[0081] The above plasticizer composition may be the plasticizer composition described above.

[0082] The above plasticizer composition may be included in an amount of 5 parts by weight or more and 150 parts by weight or less based on 100 parts by weight of the thermoplastic resin, and preferably may be included in an amount of 5 parts by weight or more, 10 parts by weight or more, 15 parts by weight or more, or 20 parts by weight or more and 150 parts by weight or less, 140 parts by weight or less, 130 parts by weight or less, or 120 parts by weight or less.

[0083] The above thermoplastic resin may be any resin known in the art. For example, one or more mixtures selected from the group consisting of straight vinyl chloride polymer, paste vinyl chloride polymer, ethylene vinyl acetate copolymer, ethylene polymer, propylene polymer, polyketone, polystyrene, polyurethane, natural rubber, synthetic rubber, and thermoplastic elastomer may be used, but are not limited thereto.

[0084] Generally, the resin in which the plasticizer composition is used can be manufactured into a resin product through melt processing or plastisol processing, and the melt-processed resin and the plastisol-processed resin may be produced differently depending on each polymerization method.

[0085] For example, when vinyl chloride polymers are used in melt processing, solid resin particles with a large average particle size are produced by methods such as suspension polymerization, and such vinyl chloride polymers are called straight vinyl chloride polymers; however, when used in plastisol processing, resin in a sol state as fine resin particles is produced by methods such as emulsion polymerization, and such vinyl chloride polymers are called paste vinyl chloride resins.

[0086] At this time, in the case of the straight vinyl chloride polymer, it is preferable that the plasticizer composition be included in the range of 5 to 100 parts by weight per 100 parts by weight of the polymer, and in the case of the paste vinyl chloride polymer, it is preferable that the plasticizer composition be included in the range of 40 to 120 parts by weight per 100 parts by weight of the polymer.

[0087] The resin composition may further include a filler. The filler may be in an amount of 0 to 300 parts by weight, preferably 50 to 200 parts by weight, and more preferably 100 to 200 parts by weight, based on 100 parts by weight of the resin.

[0088] The above filler may be any filler known in the art and is not particularly limited. For example, it may be a mixture of one or more selected from silica, magnesium carbonate, calcium carbonate, light carbon, talc, magnesium hydroxide, titanium dioxide, magnesium oxide, calcium hydroxide, aluminum hydroxide, aluminum silicate, magnesium silicate, and barium sulfate.

[0089] In addition, the resin composition may further include other additives such as stabilizers as needed. For example, the other additives such as stabilizers may each be in an amount of 0 to 30 parts by weight, preferably 1 to 20 parts by weight, based on 100 parts by weight of the resin.

[0090] The above stabilizer may be a calcium-zinc-based (Ca-Zn-based) stabilizer, such as a calcium-zinc complex stearate, or a barium-zinc-based (Ba-Zn-based) stabilizer, but is not specifically limited thereto.

[0091] The resin composition described above can be applied to both melt processing and plastisol processing as described above. For example, melt processing may be applied to calendering, extrusion, or injection processing, and plastisol processing may be applied to coating processing, etc.

[0092]

[0093] Examples

[0094] Hereinafter, the present invention will be described in more detail through examples and experimental examples to specifically explain the invention, but the present invention is not limited by these examples and experimental examples. The embodiments according to the present invention may be modified in various different forms, and the scope of the present invention should not be interpreted as being limited to the embodiments described below. The embodiments of the present invention are provided to more completely explain the invention to those with average knowledge in the art.

[0095]

[0096] Preparation Example 1

[0097] 381 g of pyromellitate and 1016 g of 2-ethylhexanol were added to a 3-liter, four-necked reactor equipped with a cooler, condenser, decanter, reflux pump, temperature controller, and stirrer, and 0.9 g of tetra-n-butyl titanate was added as a catalyst. Subsequently, the esterification reaction was carried out for about 3 hours while gradually increasing the temperature of the reactor to about 230°C under atmospheric pressure and a nitrogen atmosphere, and the reaction was terminated when the acid value of the reactant reached 0.1 (mg KOH / g). Afterward, unreacted raw materials were removed by distillation under reduced pressure conditions to produce tetra(2-ethylhexyl) pyromellitate (TOPM).

[0098]

[0099] Preparation Example 2

[0100] 381 g of pyromellitate acid and 1123 g of isononanol were added to a 3-liter, four-necked reactor equipped with a cooler, condenser, decanter, reflux pump, temperature controller, and stirrer, and 0.9 g of tetra-n-butyl titanate was added as a catalyst. Subsequently, the esterification reaction was carried out for about 4 hours while gradually increasing the temperature of the reactor to about 230°C under atmospheric pressure and a nitrogen atmosphere, and the reaction was terminated when the acid value of the reactant reached 0.1 (mg KOH / g). Afterward, unreacted raw materials were removed by distillation under reduced pressure conditions to produce tetraisononyl pyromellitate (TINPM).

[0101]

[0102] Preparation Example 3

[0103] 384 g of anhydrous trimellitate and 1000 g of 2-ethylhexanol were added to a 3-liter, four-necked reactor equipped with a cooler, condenser, decanter, reflux pump, temperature controller, and stirrer, and 0.4 g of tetra-n-butyl titanate was added as a catalyst. Subsequently, the esterification reaction was carried out for about 3 hours while gradually increasing the temperature of the reactor to about 230°C under atmospheric pressure and a nitrogen atmosphere, and the reaction was terminated when the acid value of the reactant reached 0.1 (mg KOH / g). Afterward, unreacted raw materials were removed by distillation under reduced pressure conditions to produce tri(2-ethylhexyl) trimellitate (TOTM).

[0104]

[0105] Preparation Example 4

[0106] 500 g of terephthalic acid and 1176 g of 2-ethylhexanol were added to a 3-liter, four-necked reactor equipped with a cooler, condenser, decanter, reflux pump, temperature controller, and stirrer, and 1.2 g of tetra-n-butyl titanate was added as a catalyst. Subsequently, the esterification reaction was carried out for about 6 hours while gradually increasing the temperature of the reactor to about 230°C under atmospheric pressure and a nitrogen atmosphere, and the reaction was terminated when the acid value of the reactant reached 0.1 (mg KOH / g). Afterward, unreacted raw materials were removed by distillation under reduced pressure conditions to produce di(2-ethylhexyl) terephthalate (DOTP).

[0107]

[0108] Each plasticizer composition was prepared by mixing the compounds prepared in the above preparation examples in the weight ratios listed in Table 1 below.

[0109] Pyromellilate trimellitate terephthalate Example 1 TOPM90 TOTM10 -- Example 2 TOPM90 -- DOTP10 Example 3 TOPM90 TOTM5 DOTP5 Example 4 TOPM80 TOTM20 -- Example 5 TOPM80 -- DOTP20 Example 6 TOPM80 TOTM10 DOTP10 Comparative Example 1 TOPM100 ---- Comparative Example 2 TIN PM100 ---- Comparative Example 3 -- TOTM100 -- Comparative Example 4 TOPM70 TOTM30 -- Comparative Example 5 TOPM70 -- DOTP30 Comparative Example 6 TOPM30 TOTM70 -- Comparative Example 7 TOPM30 -- DOTP70

[0110] Experimental Example 1. Evaluation of Physical Properties of Plasticizer Composition

[0111] For the plasticizer compositions prepared in the above examples and comparative examples, each physical property was measured and evaluated through the following method.

[0112] 1) Preparation conditions: 100 parts by weight of polyvinyl chloride (LS100, LG Chem), 50 parts by weight of a plasticizer composition, 30 parts by weight of a filler (OMYA1T), and 5 parts by weight of a stabilizer (RUP-144) were mixed and mixed at 700 rpm and 98°C, and a specimen was prepared by processing using a roll mill at 165°C for 4 minutes, and using a press at 190°C for 2.5 minutes (low pressure) and 2 minutes (high pressure).

[0113] 2) Plasticization efficiency: Plasticization efficiency was evaluated using 'hardness'. The hardness refers to Shore hardness (Shore "A" and Shore "D") at 25°C measured using ASTM D2240, and was measured under conditions of 3T 10s. A lower hardness indicates better plasticization efficiency.

[0114] 3) Migration Resistance: Migration resistance was evaluated through 'migration loss'. In accordance with KSM-3156, a test specimen with a thickness of 1 mm was obtained, and after attaching tracing paper to both sides of the specimen, 2 kgf / cm² 2A load was applied. After leaving the test specimen in a hot air circulating oven (80°C) for 3 days, it was removed and cooled at room temperature for 4 hours. After removing the oil paper attached to both sides of the test specimen, the weight of the specimen before and after the experiment was measured, and the amount of migration loss was calculated using the following Equation 1. A smaller amount of migration loss indicates superior migration resistance.

[0115] [Mathematical Formula 1]

[0116] Migration Loss (%) = {(Initial weight of specimen at room temperature - Weight of specimen after oven storage) / Initial weight of specimen at room temperature} x 100

[0117] 4) Heat loss: After maintaining a specimen with a thickness of 1 mm in a gear oven at 150°C for 168 hours, the change in weight of the specimen before and after the test was measured, and the heat loss was calculated using the following Equation 2. The lower the heat loss, the better the physical properties of the plasticizer composition.

[0118] [Mathematical Formula 2]

[0119] Heat Loss (Weight%) = {(Initial Specimen Weight - Specimen Weight After Processing) / Initial Specimen Weight} x 100

[0120] 5) Mechanical properties: The mechanical properties of the plasticizer composition were evaluated using tensile strength and elongation. Tensile strength was calculated according to the ASTM D638 method by using a UTM (manufacturer: Instron, model name: 4466), pulling at a crosshead speed of 200 mm / min (1T), measuring the point where a specimen with a thickness of 1 mm breaks, and using the following Equation 3.

[0121] [Mathematical Formula 3]

[0122] Tensile strength (kgf / cm2) = Load (kgf) / Thickness (cm) x Width (cm)

[0123] The 'elongation rate' was calculated using the following Equation 4, after measuring the point where a specimen with a thickness of 1 mm is cut using the above UTM according to the ASTM D638 method at a crosshead speed of 200 mm / min (1T).

[0124] [Mathematical Formula 4]

[0125] Elongation (%) = Length after elongation / Initial length x 100

[0126] 6) Aging resistance: After storing a specimen with a thickness of 1 mm in an oven at 150°C for 168 hours, the tensile strength and elongation were measured using the method described above, and the ratio (residual ratio) of the tensile strength and elongation before oven storage and the tensile strength and elongation after oven storage was calculated.

[0127] 7) Oil resistance: A specimen with a thickness of 1 mm was immersed in IRM-902 oil at 80°C for 4 hours, and then the tensile strength and elongation were measured using the method described above. The ratio (residual ratio) of the tensile strength and elongation before storage in oil and the tensile strength and elongation after storage in oil was calculated.

[0128] 8) Volume resistance: For a specimen with a thickness of 1 mm and a width and length of 100 mm each, a single current of 500 V was applied using HIOKI’s SM-8200 SUPER MEGOHMMETERS product, and the volume resistance was measured after 1 minute.

[0129] 9) Absorption rate: Under conditions of 73℃ and 60rpm, 100 parts by weight of polyvinyl chloride resin and 50 parts by weight of a plasticizer composition were mixed using a Planatary mixer (Brabender, P600), and the time required until the torque of the mixer stabilized was measured.

[0130]

[0131] The above measurement results are summarized in Tables 2 and 3 below.

[0132] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Fixing Efficiency Shore A 96.296.196.196.096.096.0 Shore D 52.852.352.452.451.852.0 Transfer Loss (%) 1.111 1.261.201.231.871.54 Heating Loss (%) 4.03 6.364.665.748.556.25 Mechanical Properties Tensile Strength (kg / cm²) 2 )203.5 194.4 201.7 202.9 189.2 201.0 Elongation (%) 315.4 312.7 315.0 316.1 309.8 315.7 Residual tensile strength against aging (%) 95.1 98.5 97.5 93.4 95.6 93.8 Residual elongation (%) 60.1 55.9 59.7 52.3 50.3 51.1 Residual tensile strength against oil (%) 89.8 86.9 88.3 88.0 82.5 86.3 Residual elongation (%) 79.3 80.2 80.4 78.5 78.6 77.8 Volume resistance Sheet(x10 13 Ωcm)68.5 64.5 65.4 50.8 56.1 52.3 Absorption rate (mm:ss)14:52 14:12 13:30 14:20 13:50 14:00

[0133] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Comparative Example 7 Fixability Shore A 97.0 99.4 95.5 95.8 96.0 95.8 92.0 Shore D 54.7 57.9 50.1 52.0 51.5 51.3 47.8 Transfer Loss (%) 1.1 11.6 11.8 01.5 43.5 71.7 06.55 Heating Loss (%) 3.7 64.2 0 10.3 18.5 410.2 59.2 314.7 Mechanical Properties Tensile Strength (kg / cm²) 2 )187.4201.7209.7205.4189.4201.3177.6 Elongation (%) 314.5314.7318.6316.2304.6311.7278.5 Tensile Residue (%) 98.680.179.782.394.180.277.2 Residue (%) 60.849.625.234.826.627.810.3 Tensile Residue (%) 87.186.586.086.278.585.856.7 Residue (%) 82.078.977.778.364.178.020.3 Volume Resistance Sheet(x10 13Ωcm)75.0 25.8 31.4 33.7 24.8 31.5 12.3 Absorption rate(mm:ss)15:56 34:50 11:40 13:55 13:20 12:10 8:50

[0134] Referring to the results of Tables 2 and 3 above, the plasticizer composition according to the embodiment of the present invention exhibits superior plasticizing efficiency with lower hardness compared to the plasticizer compositions of Comparative Examples 1 and 2, which contain pyromellitate alone. In particular, it showed superior effects in terms of tensile strength and absorption rate compared to the plasticizer composition of Comparative Example 1, which has the same number of carbon atoms in the alkyl group. Furthermore, it was confirmed that the plasticizer composition of Comparative Example 3, which uses trimellitate—a minor component in the plasticizer composition of the present invention—alone, is inferior in terms of heat loss, aging resistance, oil resistance, and insulation. Finally, in the case of the plasticizer compositions of Comparative Examples 4 to 7, which contain trimellitate or terephthalate together with pyromellitate in the same manner as the embodiment of the present invention but with an excessive amount, it was confirmed that the migration resistance, heat loss, aging resistance, oil resistance, and insulation were inferior compared to the embodiment.

[0135] From this, it can be seen that the plasticizer composition of the present invention includes a relatively small amount of trimellitate or terephthalate along with pyromellitate having an alkyl group satisfying a certain number of carbon atoms, thereby having excellent various physical properties and an excellent balance between them.

Claims

1. A compound represented by the following chemical formula 1; and Compounds represented by the following chemical formula 2 or 3; comprising, A plasticizer composition in which the total content of a compound represented by Chemical Formula 2 or 3, based on the total weight of the plasticizer composition, is 20 weight% or less: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] In the above formula, R1 to R9 are each independently an alkyl group having 8 or 9 carbon atoms.

2. In Paragraph 1, A plasticizer composition in which the compound represented by the above chemical formula 1 is included in an amount of 70% by weight or more based on the total weight of the plasticizer composition.

3. In Paragraph 1, A plasticizer composition having a total content of the compound represented by Formula 2 or 3, based on the total weight of the plasticizer composition, of 0.1% by weight or more and 15% by weight or less.

4. In Paragraph 1, The above R1 to R4 are each independently plasticizer compositions in which alkyl groups having 8 carbon atoms are each independent.

5. In Paragraph 4, The above R1 to R4 are plasticizer compositions in which 2-ethylhexyl groups are present.

6. In Paragraph 1, The above R5 to R7 are each independently plasticizer compositions in which alkyl groups having 8 carbon atoms are independently formed.

7. In Paragraph 6, The above R5 to R7 are plasticizer compositions in which 2-ethylhexyl groups are present.

8. In Paragraph 1, The above R8 and R9 are each independently plasticizer compositions in which alkyl groups having 8 carbon atoms.

9. In Paragraph 8, The above R8 and R9 are plasticizer compositions in which 2-ethylhexyl groups are present.

10. In Paragraph 1, A plasticizer composition in which R1 to R9 are identical to each other.

11. Thermoplastic resin; and A resin composition comprising a plasticizer composition according to any one of claims 1 to 10 above.

12. In Paragraph 11, A resin composition comprising a plasticizer composition in an amount of 5 parts by weight or more and 150 parts by weight or less per 100 parts by weight of the thermoplastic resin.

13. In Paragraph 11, The above resin composition is one or more selected from the group consisting of ethylene vinyl acetate, polyethylene, polyketone, polypropylene, polyvinyl chloride, polystyrene, polyurethane, and thermoplastic elastomer.

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