ESTER-BASED COMPOUND AND USE THEREOF

Abstract

Provided are a novel ester-based compound and a use thereof. A use of a novel ester-based compound for improving heat resistance and compatibility as a plasticizer is provided. When the ester-based compound according to the present invention is used as the plasticizer of a heat-resistant resin composition, a synergistic effect on improvement of physical properties such as migration resistance and heating loss is provided to contribute to improvement of the physical properties of a molded article, and due to a rapid absorption rate and a short melting time, processability of the heat-resistant resin composition may be improved.

Claims

1. A compound represented by the following Chemical Formula 1: ##STR00012## wherein R.sub.1 and R.sub.2 are independently of each other C1-C10 alkyl; and L.sub.1 is C1-C10 alkylene, and non-adjacent —CH.sub.2— of the alkylene may be replaced in a manner in which O atoms are not directly connected to each other.

2. The compound of claim 1, wherein in Chemical Formula 1, R.sub.1 and R.sub.2 are independently of each other C3-C10 alky, and L.sub.1 is C2-C6 alkylene.

3. The compound of claim 1, wherein in Chemical Formula 1, R.sub.1 and R.sub.2 are independently of each other C3-C10 alkyl, and L.sub.1 is selected from a structure represented by the following Chemical Formula A: ##STR00013## wherein L.sub.2 and L.sub.3 are independently of each other ethylene or propylene; Y is O; and a is an integer of 1 or 2.

4. The compound of claim 1, wherein in Chemical Formula 1, R.sub.1 and R.sub.2 are independently of each other branched C3-C10 alkyl.

5. An ester-based plasticizer composition comprising a compound represented by the following Chemical Formula 1: ##STR00014## wherein R.sub.1 and R.sub.2 are independently of each other C1-C10 alkyl; and L.sub.1 is C1-C10 alkylene, and non-adjacent —CH.sub.2— of the alkylene may be replaced in a manner in which O atoms are not directly connected to each other.

6. The ester-based plasticizer composition of claim 5, wherein 30 wt % or more of the compound represented by Chemical Formula 1 is comprised, based on a total weight of the ester-based plasticizer composition.

7. A method of preparing an ester-based plasticizer composition, the method comprising: performing a transesterification reaction of a compound represented by the following Chemical Formula 2 and a polyhydric alcohol to prepare an ester-based plasticizer composition including a compound represented by the following Chemical Formula 1: ##STR00015## wherein R.sub.1 and R.sub.2 are independently of each other C1-C10 alkyl; and L.sub.1 is C1-C10 alkylene, and non-adjacent —CH.sub.2— of the alkylene may be replaced in a manner in which O atoms are not directly connected to each other.

8. The method of preparing an ester-based plasticizer composition of claim 7, wherein the polyhydric alcohol is a compound including an alkylene group having 2 to 10 carbon atoms.

9. The method of preparing an ester-based plasticizer composition of claim 7, wherein 30 wt % or more of the compound represented by Chemical Formula 1 is included, based on a total weight of the ester-based plasticizer composition.

10. The method of preparing an ester-based plasticizer composition of claim 9, wherein a compound represented by the following Chemical Formula 2 is included as a remainder, based on the total weight of the ester-based plasticizer composition: ##STR00016## wherein R.sub.1 and R.sub.2 are independently of each other C1-C10 alkyl.

11. A vinyl chloride-based resin composition comprising the ester-based plasticizer composition of claim 5.

12. The vinyl chloride-based resin composition of claim 11, wherein 5 to 100 parts by weight of the ester-based plasticizer composition is comprised, based on 100 parts by weight of the vinyl chloride-based resin.

13. The vinyl chloride-based resin composition of claim 11, further comprising: a heat stabilizer, a filler, or a combination thereof.

14. The vinyl chloride-based resin composition of claim 11, wherein the vinyl chloride-based resin composition has a ratio of heating loss of 2.0% or less, the ratio of heating loss being measured with respect to a weight of an initial specimen measured at room temperature after being heated at 120° C. for 72 hours in accordance with a test method of ASTM D638.

15. A molded article manufactured from the vinyl chloride-based resin composition of claim 11.

Description

Example 1

[0161] To a 1 L reactor equipped with a temperature sensor, a mechanical agitator, a condenser, a decanter, and a nitrogen injector, 500 g of cyclohexane diester (Hanwha Chemical Corporation, Eco-DEHCH) and 55.4 g of 1,4-butanediol were introduced, and the temperature was raised to 220° C. with stirring under a nitrogen condition. After heating, 0.2 g of tetra-N-butyl titanate (TNBT) was introduced, the temperature was raised to 220° C., and a transesterification reaction was performed for 8 hours. When the reaction was completed, cooling to 90° C. was performed, a 1 M NaOH solution was introduced, and filtration was performed using diatomaceous earth. Thereafter, unreacted alcohol, water, and impurities were removed using a rotary evaporation concentrator, and an ester-based plasticizer composition as the final product was obtained.

[0162] The obtained ester plasticizer composition was analyzed by GPC to confirm a DEHCH content (%), based on the total weight. The results are shown in the following Table 1.

[0163] In addition, the ester-based plasticizer composition prepared by the preparation method was used to manufacture a specimen. The manufacture of the specimen was performed by blending 400 g of PVC (polymerization degree: 1000) with 200 g of a plasticizer, 32 g of a composite heat stabilizer (RUP-110), and 80 g of calcium carbonate and working with a roll mill at 170° C. for 3 minutes to manufacture a 1 mm sheet. Thereafter, press working was performed by preheating at 180° C. for 3 minutes, heating for 9 minutes, and cooling for 3 minutes to manufacture a specimen having a thickness of 3 mm.

[0164] The specimen was used, and the results of the physical properties measured by the evaluation method are shown in Tables 1 and 2.

Examples 2 to 4

[0165] An ester-based plasticizer composition was obtained in the same manner as in Example 1, except that the introduction amount of the polyhydric alcohol was changed as in the following Table 1.

[0166] The DEHCH contents (%) of the obtained ester plasticizer composition based on the total weight were confirmed by GPC analysis, and the results are shown in the following Table 1.

[0167] In addition, the specimen was manufactured in the same manner as in Example 1, and the results of the physical properties measured by the evaluation method are shown in the following Tables 1 and 2.

Comparative Example 1

[0168] Commercially available cyclohexane diester (Hanwha Chemical Corporation, Eco-DEHCH) was used.

[0169] The specimen was manufactured in the same manner as in Example 1, and the results of the physical properties measured by the evaluation method are shown in the following Tables 1 and 2.

TABLE-US-00001 TABLE 1 Example Example Example Example Comparative 1 2 3 4 Example 1 Introduction amount 0.5 1 1.5 2 — of diol (DEHCH mole %) Hardness (Shore A) 82.5 84.5 89.2 93.8 79.3 Migration amount (%) 0.04 0 0 0 0.14 Heating loss 1.37 1.3 1.03 0.74 2.58 (specimen, %) Tensile strength 171 174 178 186 163 (kg/cm.sup.2) Elongation (%) 484 482 486 421 444 DEHCH content (%) 34.3 53.8 47.2 4.2 100

TABLE-US-00002 TABLE 2 Comparative Examples Examples 1 2 3 4 1 Tensile residual rate 99.1 99.4 99.9 100 98.3 (%) Stretch residual rate 98.9 99.2 99.5 100 98.6 (%)

[0170] As shown in Table 1, it is recognized that when the plasticizer composition including the ester-based compound according to the present invention was employed, an excellent effect on migration resistance and heating loss was shown. Specifically, according to the present invention, it was confirmed that a migration amount of 28.6% or less (Example 1) as compared with Comparative Example 1 was implemented, and the migration amount was almost not confirmed. In addition, it was confirmed that a heating loss of 53.1% or less (Example 1) as compared with Comparative Example 1 was implemented and a significantly low heating loss of 28.6% was implemented. In addition, according to the present invention, the tensile strength and the elongation which were equivalent to or higher than cyclohexane diester (Hanwha Chemical Corporation, Eco-DEHCH) used in Comparative Example 1 were implemented, and thus, it is expected that the present invention may be usefully applied as a material to replace DEHCH.

[0171] As shown in Table 2, when the plasticizer composition including the ester-based compound according to the present invention was employed, the tensile strength and the elongation which were equivalent to or higher than cyclohexane diester (Hanwha Chemical Corporation, Eco-DEHCH) were able to be implemented, of course, and an advantage in the tensile residual rate and the stretch residual rate was also able to be provided.

[0172] Hereinabove, although the present invention has been described by specific matters, Examples, and Comparative Examples, they have been provided only for assisting in the entire understanding of the present invention. Therefore, the present invention is not limited to the above Examples. Various modifications and changes may be made by those skilled in the art to which the present invention pertains from this description.

[0173] Therefore, the spirit of the present invention should not be limited to the above-described exemplary embodiments, and the following claims as well as all modified equally or equivalently to the claims are intended to fall within the scope and spirit of the invention.