JP-2026514227-A - Polyester polymer, method for producing polyester polymer, and molded article

Abstract

This invention relates to a polyester polymer with high bio-content and molecular weight, as well as excellent optical properties, a method for producing the polyester polymer, and molded articles.

Inventors

• ヨンジュ・イ
• ドンチョル・チェ
• チョル・ウン・キム
• スヒョン・チョ
• キョンミン・キム
• ドンギョン・カン

Assignees

• エルジー・ケム・リミテッド

Dates

Publication Date

20260507

Application Date

20240820

Priority Date

20230907

Claims (19)

1. It contains repeating units represented by the following chemical formula 1, The biomass content measured by ASTM D6866-22 is 40% or more. A polyester polymer in which, when exposed to the external environment at room temperature for more than 10 days, more than 20% by weight decomposes relative to the weight of the initial polymer. In the aforementioned chemical formula 1, L1 is an alkylene group with 3 carbon atoms, L2 is an alkylene group having 1 to 10 carbon atoms.
2. The polyester polymer according to claim 1, wherein the polyester polymer has a number-average molecular weight of 10,000 g/mol or more and 200,000 g/mol or less.
3. The polyester polymer according to claim 1, wherein the weight-average molecular weight of the polyester polymer is 5,000 g/mol or more and 600,000 g/mol or less.
4. The polyester polymer according to claim 1, wherein the polyester polymer contains 90 mol% or more of the repeating units represented by chemical formula 1, relative to the total repeating units.
5. The polyester polymer according to claim 1, wherein the polyester polymer consists of repeating units represented by the chemical formula 1.
6. A method for producing a polyester polymer, comprising the steps of: adding a C3 diol compound and a dicarboxylate compound and reacting them at a temperature of 50°C to 200°C and a pressure of 10 torr to 760 torr to produce an oligomer; and reacting the oligomer at a temperature of 50°C to 200°C and a pressure of 1 torr to produce a polyester polymer.
7. The method for producing a polyester polymer according to claim 6, wherein, when the polyester polymer is exposed to the external environment at room temperature for 10 days or more, 20% or more of the original polymer's weight decomposes.
8. The step of adding the C3 diol compound and dicarboxylate compound and reacting them under conditions of a temperature of 50°C to 200°C and a pressure of 10 torr to 760 torr to produce an oligomer; A method for producing a polyester polymer according to claim 6, comprising the step of adding a diol compound and a dicarboxylate compound and reacting them for 1 hour to 30 hours under conditions of a temperature of 90°C to 200°C and a pressure of 50 torr to 700 torr to produce an oligomer.
9. The step of reacting the oligomer at a temperature of 90°C to 200°C and a pressure of 1 torr or less to produce a polyester polymer; A method for producing a polyester polymer, comprising the step of reacting the oligomer with the oligomer for 1 hour to 30 hours under conditions of a temperature of 50°C to 200°C and a pressure of 1 torr or less.
10. A method for producing a polyester polymer according to claim 6, wherein the chain extender is contained in an amount of less than 0.0001 parts by weight per 100 parts by weight of the total amount of the C3 diol compound and the dicarboxylate compound.
11. The method for producing a polyester polymer according to claim 6, wherein the polyester polymer has a number-average molecular weight of 1,000 g/mol or more and 200,000 g/mol or less.
12. The method for producing a polyester polymer according to claim 6, wherein the polyester polymer has a weight-average molecular weight of 5,000 g/mol or more and 600,000 g/mol or less.
13. A method for producing a polyester polymer according to claim 6, wherein the diol compound is contained in an amount of 1.01 moles or more and 1.5 moles or less per mole of the dicarboxylate compound.
14. The method for producing a polyester polymer according to claim 6, wherein the polyester polymer includes repeating units represented by the following chemical formula 1. In the aforementioned chemical formula 1, L1 is an alkylene group with 3 carbon atoms, L2 is an alkylene group having 1 to 10 carbon atoms.
15. The method for producing a polyester polymer according to claim 14, wherein the polyester polymer contains 90 mol% or more of the repeating units represented by chemical formula 1 relative to the total repeating units.
16. The method for producing a polyester polymer according to claim 14, wherein the polyester polymer consists of repeating units represented by the chemical formula 1.
17. The method for producing a polyester polymer according to claim 6, wherein the polyester polymer has a biomass content of 90% or more, as measured by ASTM D6866-22.
18. A molded article formed from a resin composition containing the polyester polymer described in claim 1.
19. The molded article according to claim 18 comprises one or more molded articles selected from the group consisting of injection molded articles, extruded articles, inflation molded articles, fibers, nonwoven fabrics, foams, adhesives, films, and sheets.

Description

This application, through mutual citation with related applications , claims the benefit of priority under Korean Patent Application No. 10-2023-0119288 dated September 7, 2023, and Korean Patent Application No. 10-2024-0097523 dated July 23, 2024, and all content disclosed in the documents of said Korean patent applications is incorporated herein by reference. This invention relates to polyester polymers, methods for producing polyester polymers, and molded articles. Unlike existing petroleum-based resins such as polystyrene, polyvinyl chloride, and polyethylene, biodegradable polyester polymers offer benefits such as preventing the depletion of petroleum resources and reducing carbon dioxide emissions, thus mitigating the environmental pollution associated with petroleum-based plastic products. Therefore, as environmental pollution caused by waste plastics becomes a significant social issue, efforts are being made to expand the application of these polymers to product areas that currently use general plastics (petroleum-based resins), such as food packaging materials and containers, and electronic product cases. However, existing polyester polymers have problems such as high yellowness in the polymer obtained after polymerization, or difficulty in obtaining high molecular weight polymers. While color-improving additives like toners or chain extenders can be used to solve these problems, this may be burdensome in terms of raw material costs. Furthermore, with growing concerns about global warming and climate change due to the depletion of petroleum resources and the increase and accumulation of carbon dioxide emissions, there is a demand for polymers that use raw materials obtained from biomass resources such as plants. Conventional polyester polymers are manufactured using petroleum-based monomers and are not polymerized using bio-based monomers, resulting in low bio-content and the inability to achieve carbon neutrality. Furthermore, even when bio-based monomers are used in the synthesis of polyester polymers, conventional biosynthesis using microorganisms requires large amounts of solvents in the separation and purification processes, making it neither environmentally friendly nor economically viable. Therefore, research is needed on environmentally friendly polyester polymers that possess excellent physical properties and high molecular weight, as well as high bio-content, without the use of additional additives. Specific details for implementing the invention The embodiments of the present invention will be described in more detail below with reference to the following examples. However, the following examples are merely illustrative of embodiments of the present invention, and the content of the present invention is not limited to these examples. Example 1 20 g (0.263 mol) of bio-derived 1,3-propanediol, 30.43 g (0.219 mol) of bio-derived succinic acid, and 0.357 g (1.05 mmol) of titanium butoxide (Ti(OBu) 4 ) were added to an oil bath reactor and mixed. The mixture was then polymerized at 90°C and 50 torr for 2 hours to produce an oligomer. Subsequently, the oligomer was further reacted at 90°C and 0.2 torr for 18 hours to produce a polyester polymer. Example 2 A polyester polymer was produced in the same manner as in Example 1, except that an oligomer was produced by polymerization reaction at 110°C and 50 torr for 2 hours, and then the oligomer was further reacted at 110°C and 0.2 torr for 18 hours. Example 3 A polyester polymer was produced in the same manner as in Example 1, except that an oligomer was produced by polymerization reaction at 130°C and 50 torr for 2 hours, and then the oligomer was further reacted at 130°C and 0.2 torr for 18 hours. Example 4 A polyester polymer was produced in the same manner as in Example 1, except that an oligomer was produced by polymerization reaction at 150°C and 50 torr for 2 hours, and then the oligomer was further reacted at 150°C and 0.2 torr for 18 hours. Example 5 A polyester polymer was produced in the same manner as in Example 1, except that an oligomer was produced by polymerization reaction at 170°C and 50 torr for 2 hours, and then the oligomer was further reacted at 170°C and 0.2 torr for 18 hours. Example 6 A polyester polymer was produced in the same manner as in Example 1, except that an oligomer was produced by polymerization reaction at 190°C and 50 torr for 2 hours, and then the oligomer was further reacted at 190°C and 0.2 torr for 18 hours. Example 7 A polyester polymer was produced in the same manner as in Example 1, except that the polymerization reaction was carried out at 150°C and 400 torr for 2 hours, then the temperature was raised to 180°C and polymerization reactions were carried out at 400 torr for 2 hours, and then at 180°C and 10 torr for 2 hours to produce an oligomer, and then the oligomer was further reacted at 180°C and 0.2 torr for 18 hours. Example 8 A polyester polymer was produced in the same manner as in Example 1, ex