Ester-based compound, composition comprising the same, method for preparing the same and resin composition comprising the same

Patent metadata

Field	Value
Publication number	US-10077230-B2
Application number	US-201615545981-A
Country	US
Kind code	B2
Filing date	May 12, 2016
Priority date	May 14, 2015
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

Abstract

The present invention relates to an ester-based plasticizer composition, a method for preparing the same and a resin composition comprising the same. The ester-based plasticizer composition according to one embodiment of the present invention is a novel terephthalate-based ester compound for a plasticizer prepared through transesterification. When the ester-based plasticizer composition is used in a resin composition, it is capable of providing excellent resistance for stress, and excellent physical properties such as migration resistance and volatility resistance as well as tensile strength and elongation rate.

First claim

What is claimed is:

1. An ester-based compound represented by the following Chemical Formula 1:

2. A plasticizer composition comprising an ester-based compound represented by the following Chemical Formula 1:

3. An ester-based plasticizer composition comprising an ester-based compound represented by the following Chemical Formula 1, an ester-based compound represented by the following Chemical Formula 2 and an ester-based compound represented by the following Chemical Formula 3:

4. The ester-based plasticizer composition of claim 3 , wherein the ester-based plasticizer composition comprises 0.5% by weight to 70% by weight of the ester-based compound represented by Chemical Formula 1, 0.5% by weight to 50% by weight of the ester-based compound represented by Chemical Formula 2 and 0.5% by weight to 85% by weight of the ester-based compound represented by Chemical Formula 3 based on the total weight of the ester-based plasticizer composition.

5. The ester-based plasticizer composition of claim 3 , wherein the ester-based plasticizer composition comprises 10% by weight to 50% by weight of the ester-based compound represented by Chemical Formula 1, 0.5% by weight to 50% by weight of the ester-based compound represented by Chemical Formula 2 and 35% by weight to 80% by weight of the ester-based compound represented by Chemical Formula 3 based on the total weight of the ester-based plasticizer composition.

6. The ester-based plasticizer composition of claim 3 , wherein a mixing ratio by weight of a sum of the ester-based compound represented by Chemical Formula 2 and the ester-based compound represented by Chemical Formula 3, and the ester-based compound represented by Chemical Formula 1 is from 95:5 to 30:70.

7. The ester-based plasticizer composition of claim 3 , which is an ether-free plasticizer.

8. A method for preparing the ester-based plasticizer composition of claim 3 ,
the method comprising conducting transesterification of an ester-based compound represented by the following Chemical Formula 3 and an alcohol represented by the following Chemical Formula 4:

9. The method for preparing the ester-based plasticizer composition of claim 8 , wherein a molar ratio of the ester-based compound represented by Chemical Formula 3 and the alcohol represented by Chemical Formula 4 is from 1:0.005 to 1:5.

10. The method for preparing the ester-based plasticizer composition of claim 8 , wherein the alcohol represented by Chemical Formula 4 is added in an amount of 0.1 parts by weight to 89.9 parts by weight based on 100 parts by weight of the ester-based compound represented by Chemical Formula 3.

11. The method for preparing the ester-based plasticizer composition of claim 8 , wherein the transesterification is conducted at a temperature from 120° C. to 190° C.

12. The method for preparing the ester-based plasticizer composition of claim 8 , wherein the transesterification is a noncatalytic reaction.

13. The method for preparing the ester-based plasticizer composition of claim 8 , the method further comprises removing the unreacted alcohol represented by Chemical Formula 4 and reaction byproducts by distillation after conducting the transesterification.

14. The method for preparing the ester-based plasticizer composition of claim 8 , wherein part of the ester-based compound represented by Chemical Formula 3 is converted to an ester-based compound represented by the following Chemical Formula 1 and an ester-based compound represented by the following Chemical Formula 2 by the transesterification:

15. The method for preparing the ester-based plasticizer composition of claim 8 , wherein the ester-based compound represented by the Chemical Formula 3 is prepared by conducting esterification of compound represented by the following Chemical Formula 5 and an alcohol represented by the following Chemical Formula 6 in the presence of a catalyst:

16. The method for preparing the ester-based plasticizer composition of claim 15 , wherein the esterification is conducted at a temperature from 80° C. to 270° C.

17. The method for preparing the ester-based plasticizer composition of claim 15 , wherein the catalyst is an organic metal catalyst comprising a Sn-based or a Ti-based, an acid catalyst comprising a sulfonic acid-based or a sulfuric acid-based, or a mixed catalyst thereof.

18. The method for preparing the ester-based plasticizer composition of claim 15 , wherein a molar ratio of the compound represented by Chemical Formula 5 and the alcohol represented by Chemical Formula 6 is from 1:1 to 1:7.

19. The method for preparing the ester-based plasticizer composition of claim 15 , wherein the alcohol represented by Chemical Formula 6 comprises at least one isomer.

20. A resin composition comprising 5 parts by weight to 100 parts by weight of the ester-based plasticizer composition of claim 3 based on 100 parts by weight of a resin comprising at least one selected from the group consisting of ethylene vinyl acetate, polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyurethane, thermoplastic elastomers and polylactic acid.

Assignees

• Lg Chemical Ltd

Inventors

• Kim Hyun Kyu
• Lee Mi Yeon
• Moon Jeong Ju
• Kim Joo Ho
• Jeong Seok Ho

Classifications

• C07C69/82 Primary

  Terephthalic acid esters · CPC title

• C07C67/03 Primary

  by reacting an ester group with a hydroxy group · CPC title

• C08L67/03

  the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings · CPC title

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title

• C08K2201/014

  Additives containing two or more different additives of the same subgroup in C08K · CPC title