WO2022114373A1 - Poudre composite de polyimide comprenant de la poudre de polymères à cristaux liquides (lcp) et son procédé de fabrication - Google Patents

Poudre composite de polyimide comprenant de la poudre de polymères à cristaux liquides (lcp) et son procédé de fabrication Download PDF

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Publication number
WO2022114373A1
WO2022114373A1 PCT/KR2020/019232 KR2020019232W WO2022114373A1 WO 2022114373 A1 WO2022114373 A1 WO 2022114373A1 KR 2020019232 W KR2020019232 W KR 2020019232W WO 2022114373 A1 WO2022114373 A1 WO 2022114373A1
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Prior art keywords
powder
composite powder
liquid crystal
polyimide composite
crystal polymer
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PCT/KR2020/019232
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English (en)
Korean (ko)
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전진석
이길남
Original Assignee
피아이첨단소재 주식회사
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Priority to CN202080107335.7A priority Critical patent/CN116490571A/zh
Publication of WO2022114373A1 publication Critical patent/WO2022114373A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C43/00—Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
    • B29C67/20—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00 for porous or cellular articles, e.g. of foam plastics, coarse-pored
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Definitions

  • the present invention relates to a polyimide composite powder comprising an LCP (liquid crystal polymer) powder and a method for manufacturing the same, and more particularly, by mixing the LCP powder in a specific ratio and preparing the polyimide composite powder through aqueous polymerization,
  • the present invention relates to a polyimide composite powder having improved moldability without degrading properties, and a method for manufacturing the same.
  • Polymer molding relates to a physical process for manufacturing a molded article from a polymer material such as plastic or rubber. It refers to a series of processes that include all manipulations of shaping without using
  • the molding processing of polymer materials is divided into primary molding (injection, extrusion, blow molding, etc.) and secondary molding (thermoforming, bonding, etc.) It is divided into vacuum molding, blow molding, foam molding, and fiber spinning.
  • Polymer molding requires designing a product of a certain quality to be cost-competitive, and even if the properties of the polymer are known, various changes appear due to conditions such as heat and pressure during the molding process, and accordingly, it is important to immediately manufacture a molded product with the desired properties. There are difficulties.
  • Polyimide generally refers to a high heat-resistant polymer produced by imidization after polycondensation of tetracarboxylic acid or a derivative thereof and aromatic diamine or aromatic diisocyanate.
  • polyimide has insolubility that does not dissolve in a solvent and infusibility that does not melt by heating, and may have various molecular structures depending on the type of monomer used.
  • pyromellitic dianhydride or biphenyltetracarboxylic dianhydride (BPDA) is used as the aromatic tetracarboxylic acid derivative component
  • BPDA biphenyltetracarboxylic dianhydride
  • ODA oxydianiline
  • p-PDA p-phenylene diamine
  • Polyimide has high heat resistance and high strength, and thus various studies are being conducted for use in automobiles, rainwater, aviation, electrical and electronic components. Polyimide has insolubility and infusibility due to the imide ring in the repeating unit, so it is generally processed in the precursor polyamic acid state. Polyimides having modified or improved stability and low water absorption, for example, polyamideimide, polyetherimide, and the like have been disclosed.
  • the polyimide resin can be produced by a relatively simple method such as mechanical stirring of a polyimide monomer, thermal imidization, or the like.
  • polyimide resin has very poor moldability and processability, so it is difficult to manufacture a molded article using a general polymer processing machine.
  • attempts have been made to manufacture molded articles through polyimide powder.
  • Polyimide powder exhibits a difference in shape from polyimide resin, making it difficult to apply commonly known molding methods such as heating and melting.
  • the production of molded products through powder is affected by various factors such as specific surface area, imidization, crystallinity, molecular weight, and particle size of the powder, and harmony of each condition is essential. Therefore, in general, a molded article is manufactured using a polyimide resin, and a separate study is required to manufacture a molded article using a polyimide powder.
  • 1,987,511 discloses a semi-crystalline, semi-aromatic thermoplastic polyimide powder prepared by using an aliphatic diamine and an aromatic tetracarboxylic acid.
  • polyimide powder has low dielectric properties, making it difficult to apply it to material parts, and due to its low dispersibility, it is difficult to mold and process, and mechanical properties are reduced in the process to solve the problem of molding and processing. The issue of becoming is still there.
  • the present inventor completed the present invention by finding that the polyimide composite powder including the LCP powder was prepared in the process of preparing the polyimide powder, and the moldability was improved while the polyimide molded article had excellent mechanical strength. .
  • the present invention intends to solve the problem that the conventional polyimide powder has low dispersibility, making it difficult to manufacture a molded article.
  • the present invention provides a polyimide composite powder comprising a polyimide powder and a liquid crystal polymer powder, wherein the liquid crystal polymer powder content is greater than 0.1 wt% based on the total weight.
  • the content of the liquid crystal polymer powder may be greater than 0.1% by weight and less than 40% by weight relative to the total weight.
  • the content of the liquid crystal polymer powder may be 10% to 30% by weight based on the total weight.
  • the present invention comprises the steps of a) preparing a polyamic acid including dianhydride and diamine; And b) adding a liquid crystal polymer to the polyamic acid of step a) and imidizing it; provides a method for producing a polyimide composite powder comprising a.
  • a polyimide molded article prepared including the step of sintering the polyimide composite powder.
  • step a) is characterized in that the polyamic acid is prepared using distilled water as a solvent.
  • step a) may be stirred for 5 minutes to 4 hours under a temperature condition of 0 to 150 °C and a pressure condition of 0.1 to 10 bar.
  • the dianhydride in step a) may be a dianhydride of Formula 1 below.
  • R 1 is the following chemical structure
  • the diamine in step a) may be a diamine of Formula 2 below.
  • R 2 is the following chemical structure
  • the liquid crystal polymer of step b) is characterized in that it is in the form of a powder.
  • the amount of the liquid crystal polymer in step b) may be greater than 0.1% by weight and less than 40% by weight based on the total weight of the polyamic acid and the liquid crystal polymer.
  • the liquid crystal polymer in step b) may be 10 to 30 wt% based on the total weight of the polyamic acid and the liquid crystal polymer.
  • the imidization in step b) may be stirring for 5 minutes to 10 hours under a temperature condition of 150 to 400 °C and a pressure condition of 10 to 300 bar.
  • a polyimide composite powder prepared by the above manufacturing method wherein the polyimide composite powder is sintered at a temperature of 100° C. to 550° C. for 1 hour to 5 hours. can be manufactured.
  • the polyimide composite powder is characterized in that it is possible to manufacture a molded article having a tensile strength of 50 Mpa or more.
  • the polyimide composite powder and its manufacturing method according to the present invention use LCP (liquid crystal polymer) powder, and unlike conventional fillers, there is an advantage in that the dispersibility of the polyimide powder is improved while excellent mechanical properties are maintained.
  • LCP liquid crystal polymer
  • It includes a polyimide powder and a liquid crystal polymer powder, and the content of the liquid crystal polymer powder is 10% to 30% by weight relative to the total weight.
  • It relates to a polyimide composite powder comprising a polyimide powder and a liquid crystal polymer powder, wherein the liquid crystal polymer powder content is greater than 0.1% by weight relative to the total weight.
  • the present invention comprises the steps of a) preparing a polyamic acid including dianhydride and diamine; and b) adding a liquid crystal polymer to the polyamic acid of step a) and imidizing the polyamic acid.
  • the present invention relates to a polyimide molded article prepared including the step of sintering the polyimide composite powder.
  • the liquid crystal polymer refers to a thermoplastic plastic exhibiting liquid crystallinity when melted, and includes, but is not limited to, a polyester-based liquid crystal, a polyesteramide-based liquid crystal, and the like.
  • the liquid crystal polymer may be a wholly aromatic polyester liquid crystal, but is not limited thereto.
  • the content of the liquid crystal polymer powder may be greater than 0.1% by weight and less than 40% by weight relative to the total weight.
  • the liquid crystal polymer powder content is 0.5 to 38% by weight, 1 to 33% by weight, 2 to 38% by weight, 3 to 37% by weight, 4 to 36% by weight, 5 to 35% by weight relative to the total weight , 5.5-34.5 wt%, 6-34 wt%, 6.5-33.5 wt%, 7-33 wt%, 7.5-32.5 wt%, 8-32 wt%, 8.5-31.5 wt%, 9-31 wt%, 9.5 to 30.5% by weight, 10 to 30% by weight.
  • the moldability is improved while maintaining excellent mechanical strength of the polyimide. Accordingly, during molding, it is not fractured and plastic deformation is easy.
  • the polyimide composite powder prepared according to an embodiment of the present invention may be a wholly aromatic polyimide, a partially alicyclic polyimide, or a wholly cyclic polyimide.
  • the polyimide composite powder prepared by the manufacturing method according to the present invention has an excellent effect of maintaining mechanical properties and improving moldability even in the case of wholly aromatics.
  • the polyimide composite powder may be manufactured at a temperature of 100° C. to 550° C., including sintering for 1 hour to 5 hours.
  • the polyimide composite powder is characterized in that it is possible to manufacture a molded article having a tensile strength of 50 Mpa or more.
  • step a) is characterized in that the polyamic acid is prepared using distilled water as a solvent.
  • the polyamic acid is prepared using distilled water as a solvent.
  • it is easy to dissolve the liquid crystal polymer using distilled water as a solvent, and since no waste solvent is generated after the polyimide composite powder is prepared, the mechanical properties do not deteriorate even after the residual solvent is removed.
  • the distilled water does not mean only distilled water in a literal sense, and it does not matter whether water in any state, such as deionized water or tap water, is used in addition to distilled water.
  • the amount of distilled water may be appropriately adjusted according to the amount of dianhydride and diamine.
  • a monomer salt may be formed by using distilled water as a solvent in the range of parts by weight.
  • step a) may be stirred for 5 minutes to 4 hours under a temperature condition of 0 to 150 °C and a pressure condition of 0.1 to 10 bar.
  • the temperature in step a) may be 30 to 130 °C, 50 to 120 °C, 60 to 100 °C.
  • the pressure in step a) may be 0.2 to 8 bar, 0.3 to 6 bar, 0.5 to 5 bar.
  • the time in step a) may be 10 minutes to 3.5 hours, 30 minutes to 3 hours. Imidization is not performed immediately under the conditions of temperature, pressure and time, so that a polyamic acid salt can be prepared.
  • the dianhydride in step a) may be a dianhydride of Formula 1 below.
  • R 1 is the following chemical structure
  • the diamine in step a) may be a diamine of Formula 2 below.
  • R 2 is the following chemical structure
  • the liquid crystal polymer of step b) is characterized in that it is in the form of a powder.
  • the amount of the liquid crystal polymer in step b) may be greater than 0.1% by weight and less than 40% by weight based on the total weight of the polyamic acid and the liquid crystal polymer.
  • the liquid crystal polymer powder content is 0.5 to 38% by weight, 1 to 33% by weight, 2 to 38% by weight, 3 to 37% by weight, 4 to 36% by weight, 5 to 35% by weight relative to the total weight , 5.5-34.5 wt%, 6-34 wt%, 6.5-33.5 wt%, 7-33 wt%, 7.5-32.5 wt%, 8-32 wt%, 8.5-31.5 wt%, 9-31 wt%, 9.5 to 30.5% by weight, 10 to 30% by weight.
  • the liquid crystal polymer has a rigid polymer structure, and the formability of the polyimide powder can be improved by changing the structure of the polymer as it is combined with the liquid crystal polymer in the polyamic acid salt state.
  • the liquid crystal polymer can maintain a constant tensile strength while changing the polymer structure by combining with the polyimide structure due to the wholly aromatic type liquid crystal polymer, and the moldability of polyimide powder due to the low molding shrinkage and linear expansion of the liquid crystal polymer can be improved
  • the imidization in step b) may be stirring for 5 minutes to 10 hours under a temperature condition of 150 to 400 °C and a pressure condition of 10 to 300 bar.
  • the temperature in step b) may be 160 to 250 °C, 170 to 240 °C, 180 to 220 °C. If the reaction temperature is less than 150 °C, the reaction rate may be excessively reduced, and if the reaction temperature exceeds 400 °C, thermal decomposition of the monomer or polymer may proceed.
  • the pressure in step b) may be 10 to 300 bar, 10 to 100 bar, 10 to 80 bar.
  • the reaction pressure is less than 10 bar, it is difficult to control the reactivity, and when the reaction pressure exceeds 300 bar, it may be difficult to obtain a high molecular weight polyimide composite powder.
  • the time in step a) may be 10 minutes to 10 hours, 10 minutes to 5 hours. If the reaction time is less than 5 minutes, the reaction does not proceed well, and if the reaction time exceeds 10 hours, hydrolysis of the polymer may occur.
  • the polyimide composite powder prepared according to an embodiment of the present invention can be manufactured through compression molding, injection molding, slush molding, blow molding, extrusion molding or spinning method, including the step of sintering.
  • the polyimide composite powder prepared according to an embodiment of the present invention has improved formability and tensile strength, so that space, aviation, electricity/electronics, semiconductors, transparent/flexible displays, liquid crystal alignment films, automobiles, precision instruments, packaging, It can be used in a wide range of industrial fields such as medical materials, separators, fuel cells and secondary batteries.
  • distilled water 255 g is placed in a 5-neck beaker-type reactor and weighed. Then, 23.46 g of pyromellitic dianhydride (PMDA) is added and dissolved by stirring through a high-speed stirrer to form tetracarboxylic acid. Transform (70 °C, 1 h). Thereafter, 21.54 g of 4,4′-oxydianiline (ODA) was added and reacted at 70° C. for 2 hours to synthesize a monomer salt. The concentration of the monomer salt at this time was 15% by weight and the solids content was -15% by weight.
  • PMDA pyromellitic dianhydride
  • ODA 4,4′-oxydianiline
  • liquid crystal polymer (LCP) in a powder state was added to the mixture of the formed monomer salts, the pressure of the high-temperature/high-pressure reactor was set to 12-15 bar, and the mixture was stirred at a temperature of 190° C. for 6 hours. Thereafter, the polyimide composite powder suspension was filtered under reduced pressure while washing with distilled water to obtain a polyimide composite powder.
  • a polyimide composite powder was prepared in the same manner as in Example 1, except that 11.25 g of liquid crystal polymer was used.
  • a polyimide composite powder was prepared in the same manner as in Example 1, except that 19.29 g of liquid crystal polymer was used.
  • a polyimide powder was prepared in the same manner as in Example 1, except that the liquid crystal polymer was not included.
  • a polyimide composite powder was prepared in the same manner as in Example 1, except that 0.045 g of liquid crystal polymer was used.
  • a polyimide composite powder was prepared in the same manner as in Example 1, except that 30.00 g of liquid crystal polymer was used.
  • the tensile strength of the specimen prepared through the above process was measured and shown in Table 1 below.
  • the tensile strength of the specimen was measured according to ASTM D1708 standard using Inslon's 5564 UTM.
  • Formability O When the composite powder was compression molded using a 100 mm ⁇ 100 mm ⁇ 10 mm mold, moldability was evaluated as O when molding was performed.
  • Moldability X Proceeding in the same manner as the above compression molding, when molding was not performed, moldability was evaluated as X.
  • the polyimide composite powders prepared according to Examples 1 to 3 of the present invention had excellent moldability, and it was found that the molded articles manufactured through this had excellent tensile strength.
  • Comparative Example 1 without LCP powder and Comparative Example 2 containing 0.1 wt% of LCP powder, it was confirmed that molded articles were not manufactured due to remarkably low moldability, and Comparative Example 3 containing 40 wt% of LCP powder It was confirmed that the tensile strength was significantly lowered.
  • the method for producing a polyimide composite powder according to the present invention has an excellent effect of improving the dispersibility of the polyimide powder by adding the LCP powder in the state of a monomer salt, which is an intermediate step of the polyimide composite powder production step.
  • it has excellent properties with improved moldability while maintaining excellent mechanical strength by adjusting the amount of LCP powder added.
  • the reaction temperature is low and the reaction time is short, so the efficiency in the manufacturing process is high, and it is eco-friendly by using water as a reaction solvent, and has the effect of cost reduction.
  • the polyimide composite powder according to the present invention has improved dispersibility and moldability, so that it is easy to manufacture a molded article using the polyimide powder. In particular, since it can exhibit certain characteristics according to the content of the LCP powder, there is industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne une poudre composite de polyimide comprenant une poudre de polymère à cristaux liquides (LCP) et son procédé de fabrication et, plus spécifiquement, une poudre composite de polyimide comprenant une poudre de polyimide et une poudre de polymère à cristaux liquides, la teneur en poudre de polymère à cristaux liquides étant supérieure à 0,1% en poids sur la base du poids total de la poudre composite, et un procédé de fabrication d'une poudre composite de polyimide, le procédé comprenant les étapes suivantes: a) la préparation de l'acide polyamique contenant du dianhydride et de la diamine; et b) l'ajout d'un polymère à cristaux liquides à l'acide polyamique de l'étape a), suivie d'une réaction d'imidisation. La présente invention peut améliorer l'aptitude au moulage sans dégrader les propriétés mécaniques en utilisant une poudre de LCP aux rapports spécifiques et employant une polymérisation aqueuse.
PCT/KR2020/019232 2020-11-30 2020-12-28 Poudre composite de polyimide comprenant de la poudre de polymères à cristaux liquides (lcp) et son procédé de fabrication WO2022114373A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202080107335.7A CN116490571A (zh) 2020-11-30 2020-12-28 包含液晶高分子粉末的聚酰亚胺复合粉末及其制备方法

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KR10-2020-0164703 2020-11-30
KR1020200164703A KR102548758B1 (ko) 2020-11-30 2020-11-30 Lcp 분말을 포함하는 폴리이미드 복합 분말 및 이의 제조방법

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WO2022114373A1 true WO2022114373A1 (fr) 2022-06-02

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100567089B1 (ko) * 1997-01-31 2006-03-31 폴리머스 오스트레일리아 프로프라이어터리 리미티드 고분자배합물 및 폴리에스테르의 변성방법
JP2006143796A (ja) * 2004-11-17 2006-06-08 Toyobo Co Ltd ポリイミド成形体およびその製造方法
KR20160096565A (ko) * 2016-07-22 2016-08-16 연세대학교 원주산학협력단 물을 분산매로 사용한 폴리이미드의 제조방법
JP2018111304A (ja) * 2017-01-12 2018-07-19 株式会社リコー 立体造形用樹脂粉末、立体造形物及び立体造形物の製造方法
KR20190100729A (ko) * 2018-02-21 2019-08-29 주식회사 엘지화학 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 및 이를 이용한 액정 배향막

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2980201B1 (fr) 2011-09-20 2014-10-24 Rhodia Operations Polyimides thermoplastiques

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100567089B1 (ko) * 1997-01-31 2006-03-31 폴리머스 오스트레일리아 프로프라이어터리 리미티드 고분자배합물 및 폴리에스테르의 변성방법
JP2006143796A (ja) * 2004-11-17 2006-06-08 Toyobo Co Ltd ポリイミド成形体およびその製造方法
KR20160096565A (ko) * 2016-07-22 2016-08-16 연세대학교 원주산학협력단 물을 분산매로 사용한 폴리이미드의 제조방법
JP2018111304A (ja) * 2017-01-12 2018-07-19 株式会社リコー 立体造形用樹脂粉末、立体造形物及び立体造形物の製造方法
KR20190100729A (ko) * 2018-02-21 2019-08-29 주식회사 엘지화학 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 및 이를 이용한 액정 배향막

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KR102548758B1 (ko) 2023-06-28
CN116490571A (zh) 2023-07-25

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