Ester compound, plasticizer composition including the same, preparation method of the plasticizer composition and resin composition including the plasticizer composition

Patent metadata

Field	Value
Publication number	US-10150727-B2
Application number	US-201515039791-A
Country	US
Kind code	B2
Filing date	Feb 5, 2015
Priority date	Feb 7, 2014
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

The present invention relates to a novel ester-based compound, an ester-based composition including the same, a preparation method of the ester-based composition and a resin composition including the ester-based composition as a plasticizer. The ester-based composition according to an embodiment of the present invention is a composition including a novel isophthalate-based ester compound for a plasticizer prepared by a trans-esterification reaction and a composition including the same. A resin composition using the ester-based composition is eco-friendly and has good physical properties such as tensile strength, elongation rate, migration resistance, volatile resistance, etc.

First claim

The invention claimed is:

1. An ester-based composition comprising compounds of the following Formula 1, Formula 2 and Formula 3:

wherein, in the above Formulae 1 to 3, R 1 and R 2 are independently C 1 -C 20 alkyl, and R 1 and R 2 are not the same, and
wherein R 1 is non-branch type alkyl, and R 2 is branch-type alkyl.

2. The ester-based composition of claim 1 , wherein R 2 comprises more carbon atoms than R 1 .

3. The ester-based composition of claim 2 , wherein R 1 is C 3 -C 10 alkyl, and R 2 C 6 -C 12 alkyl.

4. The ester-based composition of claim 3 , wherein R 1 is C 3 - C 5 alkyl, and R 2 is C 6 -C 12 alkyl.

5. The ester-based composition of claim 4 , wherein R 2 is selected from ethylhexyl, isononyl and propylheptyl.

6. The ester-based composition of claim 1 , wherein the compounds of Formula 1, Formula 2 and Formula 3 are comprised in amounts of 0.5 to 50 wt %, 0.5 to 70 wt % and 0.5 to 85 wt % with respect to a total amount of the ester-based composition.

7. The ester-based composition of claim 6 , wherein the compounds of Formula 1, Formula 2 and Formula 3 are comprised in amounts of 0.5 to 50 wt %, 10 to 50 wt % and 35 to 80 wt % with respect to a total amount of the ester-based composition.

8. The ester-based composition of claim 6 , wherein a ratio of a total amount of the compounds of Formulae 1 and 3 and an amount of the compound of Formula 2 is 95:5 to 30:70 by weight.

9. The ester-based composition of claim 1 , wherein the ester-based composition comprises compounds of the following Formula 1-1, Formula 2-1 and Formula 3-1:

10. The ester-based composition of claim 1 , wherein the ester-based composition comprises compounds of the following Formula 1-1, Formula 2-2 and Formula 3-2:

11. The ester-based composition of claim 1 , wherein the ester-based composition comprises compounds of the following Formula 1-1, Formula 2-3 and Formula 3-3:

12. The ester-based composition of claim 1 , wherein the ester-based composition comprises compounds of the following Formula 1-1, Formula 2-4 and Formula 3-4:

13. The ester-based composition of claim 1 , wherein the ester-based composition is an ether-free plasticizer.

14. A method of preparing the ester-based composition of claim 1 comprising conducting a trans-esterification reaction of a compound of the following Formula 3 with a first alcohol of the following Formula 4:

in the above formulae, R 1 and R 2 are independently C 1 -C 20 alkyl, and R 1 and R 2 are not the same, and wherein R 1 is non-branched type alkyl, and R 2 is branched-type alkyl.

15. The method of the ester-based composition of claim 14 , wherein a molar ratio of the compound of the above Formula 3 and a first alcohol of the above Formula 4 is 1:0.005 to 5.

16. The method of the ester-based composition of claim 14 , wherein an amount of the first alcohol of the above Formula 4 is 0.1 to 89.9 parts by weight with respect to 100 parts by weight of the compound of the above Formula 3.

17. The method of the ester-based composition of claim 14 , wherein the trans-esterification reaction is a non-catalytic reaction.

18. The method of the ester-based composition of claim 14 , further comprising distilling unreacted first alcohol of Formula 4 and by-products to remove after the trans-esterification reaction.

19. The method of the ester-based composition of claim 14 , wherein a portion of the compound of the above Formula 3 is transformed into a compound of the following Formula 1 and a compound of the following Formula 2:

in the above formulae, R 1 and R 2 are independently C 1 -C 20 alkyl, and R 1 and R 2 are not the same.

20. The method of the ester-based composition of claim 14 , wherein the compound of the above Formula 3 is obtained by an esterification reaction of a compound of the following Formula 5 and a second alcohol of the following Formula 6 in the presence of a catalyst:

in the above formula, R 2 is C 1 -C 20 alkyl.

21. The method of the ester-based composition of claim 20 , wherein the compound of the above Formula 5 and the second alcohol of the above Formula 6 are used in a molar ratio of 1:1 to 7.

22. The method of the ester-based composition of claim 20 , wherein the second alcohol of the above Formula 6 further comprises at least one isomer of the second alcohol.

Assignees

• Lg Chemical Ltd

Inventors

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

Classifications

• C07C67/03

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

• C07C69/80 Primary

  Phthalic acid esters · CPC title

• C07B61/00

  Other general methods · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title