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JP-2026514228-A - Polyester polymer, method for producing polyester polymer, and molded article

JP2026514228AJP 2026514228 AJP2026514228 AJP 2026514228AJP-2026514228-A

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 20% or more. A polyester polymer that, when exposed to the external environment at room temperature for 90 days or more, decomposes by 20% or more of its original weight. In the aforementioned chemical formula 1, L1 is an ethylene group, 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 1,000 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 the 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 ethylene glycol 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 the polyester polymer decomposes by 20% by weight or more relative to the initial polymer weight when exposed to the external environment at room temperature for 90 days or more.
  8. The step of adding the ethylene glycol 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 ethylene glycol and a dicarboxylate compound and reacting them for 1 hour to 30 hours at 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 according to claim 6, comprising the step of reacting the oligomer with the oligomer at a temperature of 50°C or more and 200°C or less and a pressure of 1 torr or less for 1 hour or more and 30 hours or less to produce a polyester polymer.
  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 ethylene glycol and 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. The method for producing a polyester polymer according to claim 6, wherein the ethylene glycol 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 ethylene group, 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, wherein the molded article 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. 10-2023-0119289 dated September 7, 2023, and Korean Patent Application No. 10-2024-0097522 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 have the effect of preventing the depletion of petroleum resources and suppressing carbon dioxide emissions, thus reducing the environmental pollution that is a disadvantage of petroleum-based plastic products. Therefore, as environmental pollution caused by waste plastics and other sources has emerged as a social problem, efforts are being made to expand the scope of application to product fields 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 from a raw material cost perspective. Furthermore, with growing concerns about the depletion of petroleum resources and the increasing and accumulating carbon dioxide emissions leading to global warming and climate change, there is a demand for polymers derived from biomass resources such as plants. Conventional polyester polymers are manufactured using petroleum-based monomers and are not polymerized using bio-based monomers. This results 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 for separation and purification, making it neither environmentally friendly nor economically viable. Therefore, there is a need for research into 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 (0.322 mol) of bio-derived ethylene glycol, 37.3 g (0.316 mol) of bio-derived succinic acid, and 0.2 g (1.05 mmol) of p-toluenesulfonic acid 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 instead of p-toluenesulfonic acid, 0.438 g (1.288 mmol) of titanium butoxide (Ti(buO) ₄ ) was added, and the polymerization reaction was carried out at 150°C and 400 torr for 2 hours, then the temperature was raised to 180°C and the polymerization reaction was 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 tor