WO2021054513A1 - Procédé de production d'une poudre de polyimide et poudre de polyimide ainsi produite - Google Patents

Procédé de production d'une poudre de polyimide et poudre de polyimide ainsi produite Download PDF

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Publication number
WO2021054513A1
WO2021054513A1 PCT/KR2019/013688 KR2019013688W WO2021054513A1 WO 2021054513 A1 WO2021054513 A1 WO 2021054513A1 KR 2019013688 W KR2019013688 W KR 2019013688W WO 2021054513 A1 WO2021054513 A1 WO 2021054513A1
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polyimide powder
polyimide
dispersion
powder
producing
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PCT/KR2019/013688
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English (en)
Korean (ko)
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이길남
전진석
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에스케이씨코오롱피아이 주식회사
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Publication of WO2021054513A1 publication Critical patent/WO2021054513A1/fr

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    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C08K3/042—Graphene or derivatives, e.g. graphene oxides
    • 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 method for producing a polyimide powder and to a polyimide powder produced through the same, and more particularly, to control the polymerization reaction using a mixed solvent containing graphene powder and containing water and a high boiling point organic solvent. Therefore, the present invention relates to a method for producing a polyimide powder providing a polyimide powder capable of providing a polyimide molded body having a high molecular weight and excellent tensile strength and elastic modulus, and a polyimide powder produced through the same.
  • High heat-resistant polymer materials such as polyimide are essential materials for miniaturization, lightness, high performance, and high reliability of products according to the development of advanced technologies, and are used in the form of films, molded products, fibers, paints, adhesives and composites. /It is used in a wide range of industries such as electronics, automobiles and precision equipment.
  • Polyimide has excellent mechanical strength, chemical resistance, weather resistance, and heat resistance based on the chemical stability of the imide ring.
  • it is easy to synthesize can be manufactured as a thin film, has the advantage of not needing a crosslinker for curing, and is in the spotlight as a high-functional polymer material in microelectronics and optical fields due to its excellent electrical properties.
  • a polyimide substrate that has the advantage of being light, flexible, and capable of continuous processing by replacing glass substrates, insulating films and protective coatings for semiconductor devices, surface protection materials such as flexible circuit boards and integrated circuits, and base resins, and furthermore, It can also be used when forming an interlayer insulating film or a protective film of a circuit.
  • a protective material obtained by bonding a molded article such as a polyimide film with an adhesive, a liquid polyimide resin solution, or the like can be used.
  • the first method is a two-step method in which polyamic acid (PAA), a precursor, is first synthesized by reaction of dianhydride and diamine, and polyamic acid is imidized in the next step.
  • the first step is to prepare polyamic acid.
  • Diane hydride is added to a reaction solution in which diamine is dissolved, and polyamic acid is produced by ring-opening and polyaddition reaction.
  • a polar organic solvent is mainly used.
  • the second step is to produce a polyimide by imidizing the polyamic acid prepared in the first step by dehydration and ring closure reaction through a chemical method or a thermal method.
  • a dehydrating agent typified by acid anhydrides such as acetic anhydride and an imidization catalyst typified by tertiary amines such as pyridine are added to a polyamic acid solution as a precursor. It is a method of chemically performing an imidation reaction using a solvent that is easy to form a hydrate such as pyridine, and is useful for preparing an amorphous polyimide film.
  • the thermal imidization method is the simplest step as a method of thermally imidizing a precursor polyamic acid solution by heating at 250 to 300°C.
  • Fully aliphatic polyimide synthesized using the general polyimide synthesis method described above generally has a low molecular weight and low mechanical properties.
  • the basicity of the amino group of the diamine is high, so the diamine forms a salt with amic acid instead of participating in the polymerization reaction, so that a high molecular weight polyimide cannot be obtained.
  • the second method is to use an N-silylation reaction, and in the first method, in order to increase the molecular weight by preventing salt formation, diamine and chlorotrimethylsilane are reacted to synthesize a diamine protected by an N-trimethylsilyl group, Polyimide is synthesized using this diamine. Also in this method, an organic solvent is used for the synthesis of diamines protected by N-trimethylsilyl groups and for the synthesis of polyimides.
  • the disadvantages of the N-silylation method are that the cost of the chlorotrimethyl silane reagent for synthesizing an aliphatic diamine protected by an N-trimethylsilyl group is expensive and very sensitive to moisture, making it difficult to handle, and the number average molecular weight of polyimide. It is only about 10,000, and has the disadvantage that the polyimide synthesis method becomes more complicated than the general synthesis method.
  • the third method is a method of using meta-cresol as a solvent, in which meta-cresol is added as a solvent, dianhydride and diamine are added, and the temperature is raised stepwise to react for a long time.
  • the method using meta-cresol has a long reaction time with a reaction time of 64 hours or more, and a number average molecular weight of 10,000, which cannot be satisfied, and the use of a meta-cresol solvent has a long drying time and a strong irritating odor. Have.
  • the fourth method is an in-situ sirillation method, which is intended to solve the shortcomings of the N-silylation method being sensitive to moisture.
  • diamine is added to the reactor containing the organic solvent
  • chlorotrimethylsilane is added at low temperature
  • dianhydride is added to synthesize polyamic acid protected by N-trimethylsilyl group, and the protecting group is removed, and then polyimide is passed through polyamic acid.
  • the disadvantages of the in-situ silylation synthesis method are that the reaction time is long and the molecular weight is improved, but the number average molecular weight is 80,000, which is still unsatisfactory, and the chlorotrimethylsilane reagent is expensive.
  • Korean Patent Laid-Open Publication No. 10-2016-0100392 discloses a polyimide manufacturing method in which a mixture of an oligomer and a solvent is introduced into an extruder, the solvent is removed through one or more extruder exhaust ports, and the oligomer is melt-kneaded to produce a polyimide. .
  • An object of the present invention is a dispersion preparation step of preparing a dispersion by dispersing a dianhydride compound, a diamine compound, and graphene powder in a mixed solvent, and introducing the dispersion prepared through the dispersion preparation step into a reactor and A dispersion reaction step of reacting under temperature and pressurized conditions, and a polyimide powder production step of filtering and drying the reaction product prepared through the dispersion reaction step to prepare a polyimide powder, wherein the mixed solvent is water and a high boiling point organic It is achieved by providing a method for producing a polyimide powder comprising a solvent.
  • the dispersion preparation step is made by dispersing 100 parts by weight of a dianhydride compound, 80 to 120 parts by weight of a diamine compound, and 10 to 30 parts by weight of a graphene powder in 1000 to 1200 parts by weight of a mixed solvent. do.
  • the high boiling point organic solvent is assumed to have a boiling point of 180 to 220°C.
  • the high boiling point organic solvent is made of one selected from the group consisting of N-methylpyrrolidone, dimethyl sulfoxide, and ethylene glycol.
  • the mixed solvent is composed of 100 parts by weight of water and 1 to 15 parts by weight of a high boiling point organic solvent.
  • the method for producing a polyimide powder according to the present invention exhibits an excellent effect of providing a high molecular weight polyimide powder because the polymerization reaction can be controlled using a mixed solvent containing water and a high boiling point organic solvent.
  • reaction temperature is low and the reaction time is short, indicating excellent effects of high efficiency of the manufacturing process.
  • graphene powder is contained and exhibits an excellent effect of providing a polyimide powder capable of providing a polyimide molded article having excellent tensile strength and elastic modulus.
  • the manufacturing method of the polyimide powder according to the present invention is a dispersion preparation step of preparing a dispersion by dispersing a dianhydride compound, a diamine compound, and graphene powder in a mixed solvent, and the dispersion prepared through the dispersion preparation step is added to the reactor. And a dispersion reaction step of reacting at a temperature of 150 to 400° C. and a pressurized condition, and a polyimide powder production step of filtering and drying the reaction product prepared through the dispersion reaction step to prepare a polyimide powder, and the mixed solvent Consists of water and a high boiling point organic solvent.
  • the dispersion preparation step is a step of preparing a dispersion by dispersing a dianhydride compound, a diamine compound, and graphene powder in a mixed solvent, and 100 parts by weight of a dianhydride compound, 80 to 120 parts by weight of a diamine compound, and graphene powder It is made by dispersing 10 to 30 parts by weight of the mixed solvent 1000 to 1200 parts by weight, wherein the mixed solvent includes water and a high boiling point organic solvent.
  • the dianhydride compound may be a substituted or unsubstituted aromatic or aliphatic dianhydride compound, and preferably one or two or more dianhydride compounds may be used.
  • the dianhydride compound may be a compound represented by the following formula (1).
  • R 1 may be selected from the following formulas.
  • the dianhydrad compound is pyromellitic dianhydride, 4,4'- (hexafluoroisopropylidene) dianillin, 1,2,4,5-cyclohexanetetracarboxylic dianhydride , Or 4,4'-(hexafluoroisopropylidene)dianiline.
  • the diamine compound may be a substituted or unsubstituted aromatic or aliphatic diamine, and preferably one or two or more diamines may be used.
  • the diamine compound may be a compound represented by the following formula (2).
  • R 2 is selected from the following formulas.
  • the diamine compound is 4,4'-oxydianiline, ,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 4,4'-oxydianiline, Or it may be 4,4-methylenebis(2-methylcyclohexylamine).
  • the graphene powder contains 10 to 30 parts by weight based on 100 parts by weight of the dianhydride compound, and serves to improve the tensile strength and elastic modulus of the polyimide powder according to the present invention.
  • the elastic modulus of the polyimide powder is improved, but the tensile strength may be rather reduced. If the graphene powder is not contained or is contained in an amount of less than 10 parts by weight, the tensile strength of the polyimide powder The strength and modulus of elasticity can be significantly lowered.
  • the mixed solvent in which the dianhydride compound and the diamine compound are dispersed is a mixture of water and a high boiling point organic solvent.
  • a polymerization reaction can be controlled by using a mixed solvent containing water and a high boiling point organic solvent, and a high molecular weight polyimide powder can be prepared.
  • the water may be distilled water, deionized water, tap water, and the like, and water in any state may be used.
  • the high boiling point organic solvent may be an organic solvent having a boiling point of 180 to 220°C, specifically 185 to 205°C.
  • the high boiling point organic solvent may be N-methylpyrrolidone, dimethyl sulfoxide, ethylene glycol, and one or more of these may be used together.
  • the high boiling point organic solvent may contain 1 to 15 parts by weight based on 100 parts by weight of water, more preferably 3 to 12 parts by weight based on 100 parts by weight of the water.
  • the content of the high boiling point organic solvent relative to 100 parts by weight of water is less than 1 part by weight, a precipitate may be formed after the polymerization reaction, and if the content of the high boiling point organic solvent relative to 100 parts by weight of water exceeds 15 parts by weight, high molecular weight It becomes impossible to obtain polyimide powder.
  • the mixed solvent may be used in an amount of 7 to 30 times the weight of the dianhydride compound as a reactant.
  • the dispersion reaction step is a step of introducing the dispersion prepared through the dispersion preparation step into a reactor and reacting at a temperature of 150 to 400°C and a pressurized condition, and the reaction temperature of the dispersion reaction step may be 150 to 400°C.
  • the reaction temperature is preferably 160 to 250°C, more preferably 170 to 240°C, and even more preferably 180 to 220°C. At this time, if the reaction temperature is less than 150°C, the reaction rate may be too low, and if the reaction temperature exceeds 400°C, thermal decomposition of the monomer or polymer may proceed.
  • the pressure condition in the dispersion reaction step may be 1 to 500 bar. Specifically, it is preferably 1 to 300 bar, more preferably 1 to 100 bar, and even more preferably 1 to 80 bar.
  • the reaction pressure is less than 1 bar, it is difficult to control the reactivity, and when the reaction pressure exceeds 500 bar, it may be difficult to obtain a high molecular weight polyimide powder.
  • a method of applying pressure is not particularly limited, and a commonly used method may be used. Although not limited thereto, for example, a method of forming a water vapor pressure inside a pressure vessel, a method of injecting an inert gas into the pressure vessel, or a method of compressing a pressure vessel may be used. One or two or more of the above methods may be used together.
  • the inert gas may be nitrogen, argon, helium, neon, krypton or xenon.
  • the reaction time may be 5 minutes to 5 days. Specifically, 10 minutes to 10 hours are preferable, and 10 minutes to 5 hours are more preferable. If the reaction time is less than 5 minutes, the reaction does not proceed well, and if the reaction time exceeds 5 days, hydrolysis of the polymer may occur.
  • the polyimide powder manufacturing step is a step of filtering and drying the reaction product prepared through the dispersion reaction step to prepare a polyimide powder.
  • a method of filtering and drying the reaction product in the polyimide powder manufacturing step is not particularly limited, and a method commonly used may be used. Although not limited thereto, for example, it may be washed with water and methyl alcohol and dried under vacuum.
  • the particle size and surface area of the polyimide powder can be controlled by using water and a predetermined ratio of a high boiling point organic solvent together.
  • the particle size of the polyimide powder may be 1 to 10 ⁇ m. Specifically, it may be 1 to 8 ⁇ m and 3 to 7 ⁇ m.
  • the polyimide powder prepared according to an embodiment of the present invention may be a fully aromatic polyimide, a partially aliphatic polyimide, or a fully aliphatic polyimide.
  • the polymerization reaction is controlled by using water and a small amount of a high boiling point organic solvent as a reaction solvent to prepare a high molecular weight polyimide powder.
  • the manufacturing method of the polyimide powder according to an embodiment of the present invention includes a small amount of a high-boiling organic solvent so that residual solvent after drying may be minimized, and problems such as deterioration of physical properties due to residual solvent may not occur. have.
  • the polyimide powder prepared according to an embodiment of the present invention may have excellent thermal stability.
  • the polyimide powder prepared according to an embodiment of the present invention may be used for manufacturing a molded article through compression molding, injection molding, slush molding, blow molding, extrusion molding or spinning method.
  • Polyimide powder prepared according to an embodiment of the present invention is space, aviation, electricity/electronics, semiconductors, transparent/flexible displays, liquid crystal alignment films, automobiles, precision equipment, packaging, medical materials, separators, fuel cells, and secondary batteries. Etc. It can be used in a wide range of industrial fields.
  • Example 2 Proceed in the same manner as in Example 1, except that 2 g of graphene powder was used, and a polyimide powder was prepared using a mixed solvent consisting of 200 mL of distilled water and 10 mL of N-methyl pyrrolidone.
  • Example 2 Proceed in the same manner as in Example 1, except that 2.8 g of graphene powder was used, and a polyimide powder was prepared using a mixed solvent consisting of 200 mL of distilled water and 10 mL of N-methyl pyrrolidone.
  • a polyimide powder was prepared using a mixed solvent consisting of 200 mL of distilled water and 10 mL of N-methyl pyrrolidone.
  • Example 2 Proceed in the same manner as in Example 1, but using 0.4 g of graphene powder, and using a mixed solvent consisting of 200 mL of distilled water and 10 mL of N-methyl pyrrolidone to prepare a polyimide powder.
  • polyimide powder was prepared using a mixed solvent consisting of 200 mL of distilled water and 10 mL of N-methyl pyrrolidone.
  • Each of the polyimide powders prepared in Examples 1 to 7 and Comparative Examples 1 to 3 was compression molded under 96000 psi pressure using an ASTM D1708 standard specimen mold by 2 g, and then at 100° C. for 1 hour and 250° C. in a nitrogen atmosphere. Ten specimens were prepared by heating and sintering at 450° C. for 1 hour for 1 hour.
  • the molded articles made of the polyimide powder prepared through Examples 1 to 7 of the present invention have high tensile strength and elastic modulus.
  • the method for producing a polyimide powder according to the present invention provides a high molecular weight polyimide powder because the polymerization reaction can be controlled using a mixed solvent containing water and a high boiling point organic solvent.
  • the phenomenon that occurs can be improved, and accordingly, the filtration and drying process can be easily performed, and the reaction yield is high.
  • the particle size and surface area of the polyimide powder it is possible to control the particle size and surface area of the polyimide powder, provide a polyimide powder having excellent thermal stability, and use a small amount of high-boiling organic solvent, so residual solvent is minimized after drying. It exhibits the effect of providing a polyimide powder that does not cause problems such as deterioration of properties.
  • the reaction temperature is low and the reaction time is short, so the manufacturing process is highly efficient. It is eco-friendly because water is mainly used as the reaction solvent and the amount of organic waste liquid is reduced. It is inexpensive and contains graphene powder to provide a polyimide powder that provides a molded body having high tensile strength and elasticity.
  • the method for producing a polyimide powder according to the present invention and the polyimide powder produced through the same can be used for product weight reduction and miniaturization in the display field.

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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)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne : un procédé de production d'une poudre de polyimide et une poudre de polyimide ainsi produite. Plus précisément, le procédé comprend : une étape de préparation de dispersion consistant à disperser un composé dianhydride, un composé diamine et une poudre de graphène dans un solvant mixte afin de préparer une dispersion ; une étape de réaction de dispersion consistant à introduire la dispersion préparée par l'étape de préparation de dispersion dans un réacteur et à faire réagir la dispersion à une température comprise entre 150 et 400 °C dans un état sous pression ; et une étape de production de poudre de polyimide consistant à filtrer et à sécher le produit de réaction préparé par l'étape de réaction de dispersion afin de produire une poudre de polyimide, le solvant mixte contenant de l'eau et un solvant organique à point d'ébullition élevé. Dans le procédé de production de poudre de polyimide comprenant les étapes ci-dessus, une poudre de graphène est incorporée et une réaction de polymérisation peut être régulée à l'aide d'un solvant mixte contenant de l'eau et un solvant organique à point d'ébullition élevé, et, par conséquent, le procédé fournit une poudre de polyimide ayant un poids moléculaire élevé et apte à fournir un corps moulé en polyimide présentant une excellente résistance à la traction et un excellent module d'élasticité.
PCT/KR2019/013688 2019-09-17 2019-10-17 Procédé de production d'une poudre de polyimide et poudre de polyimide ainsi produite WO2021054513A1 (fr)

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KR10-2019-0114177 2019-09-17
KR1020190114177A KR102203211B1 (ko) 2019-09-17 2019-09-17 폴리이미드 분말의 제조방법 및 이를 통해 제조된 폴리이미드 분말

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Cited By (1)

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CN115819763A (zh) * 2022-10-20 2023-03-21 慧迈材料科技(广东)有限公司 一种掺杂石墨烯的聚酰亚胺粉末制备方法

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KR20230080779A (ko) * 2021-11-30 2023-06-07 피아이첨단소재 주식회사 그래핀을 이용한 전도성이 향상된 폴리이미드 분말 및 제조방법
KR102500606B1 (ko) * 2022-04-11 2023-02-16 피아이첨단소재 주식회사 폴리이미드 분말의 제조방법 및 이에 의해 제조된 폴리이미드 분말

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819763A (zh) * 2022-10-20 2023-03-21 慧迈材料科技(广东)有限公司 一种掺杂石墨烯的聚酰亚胺粉末制备方法

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