Polyester resin and preparation method of the same

Patent metadata

Field	Value
Publication number	US-11312821-B2
Application number	US-201916772019-A
Country	US
Kind code	B2
Filing date	Mar 5, 2019
Priority date	Mar 12, 2018
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

Provided are a polyester resin having a high residual rate of isosorbide, thereby exhibiting excellent heat resistance, excellent mechanical properties such as tensile strength, Young's modulus, etc., and excellent appearance properties and transparency, and a preparation method thereof.

First claim

The invention claimed is:

1. A polyester resin comprising:
moieties of dicarboxylic acid components including terephthalic acid; and
moieties of diol components including isosorbide and 1,2-propanediol,
wherein the isosorbide-derived moieties are 5 mol % or more and the 1,2-propanediol-derived moieties are 10 mol % or more in 100 mol % of the moieties of diol components, and
wherein the diol components do not comprise diol moieties derived from ethylene glycol.

2. The polyester resin of claim 1 , wherein the moieties of diol components include 5 mol % to 70 mol % of isosorbide-derived moieties and 30 mol % to 95 mol % of 1,2-propanediol-derived moieties.

3. The polyester resin of claim 1 , wherein a glass transition temperature (Tg) is 80° C. or higher.

4. The polyester resin of claim 1 , wherein the diol components further include one or more diol compounds selected from the group consisting of C8-C40 aromatic diols and C2-C20 aliphatic diols, in addition to isosorbide and 1,2-propanediol.

5. The polyester resin of claim 1 , wherein the diol components further include 1,4-cyclohexanedimethanol, in addition to isosorbide and 1,2-propanediol, and the moieties of diol components include 5 mol % to 45 mol % of isosorbide-derived moieties, 10 mol % to 50 mol % of 1,2-propanediol-derived moieties, and the balance of 1,4-cyclohexanedimethanol-derived moieties.

6. The polyester resin of claim 1 , wherein the dicarboxylic acid components further include one or more acid components selected from the group consisting of C8-C20 aromatic dicarboxylic acid components and C4-C20 aliphatic dicarboxylic acid components, in addition to terephthalic acid.

7. The polyester resin of claim 1 , further comprising moieties of C6-C20 multifunctional carboxylic acid components, the C6-C20 multifunctional carboxylic acid components comprising three or more carboxyl groups.

8. A method of preparing a polyester resin, wherein a residual rate of isosorbide in the polyester is 40% or more, and wherein the polyester does not comprise diol moieties derived from ethylene glycol, the method comprising the steps of:
performing an esterification or transesterification reaction between dicarboxylic acid components including terephthalic acid, and diol components including isosorbide and 1,2-propanediol at a pressure of 0.2 kg/cm 2 to 3.0 kg/cm 2 and at a temperature of 200° C. to 300° C.; and
performing a polycondensation reaction of the reaction product at a reduced pressure of 400 mmHg to 0.1 mmHg and at a temperature of 240° C. to 300° C.

9. The method of claim 8 , wherein the diol components include 5 mol % to 70 mol % of isosorbide and 30 mol % to 95 mol % of 1,2-propanediol with respect to the total 100 mol % of the diol components.

10. The method of claim 8 , wherein the diol components further include 1,4-cyclohexanedimethanol.

11. The method of claim 10 , wherein the diol components include 5 mol % to 50 mol % of isosorbide, 10 mol % to 75 mol % of 1,2-propanediol, and the balance of 1,4-cyclohexanedimethanol with respect to the total 100 mol % of the diol components.

12. The method of claim 8 , wherein a molar ratio of the dicarboxylic acid components and the diol components is 1:1 to 1:3.

13. The method of claim 8 , wherein a C6-C20 multifunctional carboxylic acid component is further included in the esterification or trans esterification reaction step, the C6-C20 multifunctional carboxylic acid component comprising three or more carboxyl groups.

Assignees

• Sk Chemicals Co Ltd
• Seoul Nat Univ R&Db Foundation

Inventors

• Kim Ji-Hyun
• Kim Jong Ryang
• Ahn Cheol Hee

Classifications

• C08G63/183 Primary

  Terephthalic acids · CPC title

• C08G63/199

  Acids or hydroxy compounds containing cycloaliphatic rings · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08G63/672

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08L67/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) · CPC title