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WO2017135365A1 - Résine de polyester à cristaux liquides entièrement aromatique et son procédé de production - Google Patents

Résine de polyester à cristaux liquides entièrement aromatique et son procédé de production Download PDF

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Publication number
WO2017135365A1
WO2017135365A1 PCT/JP2017/003746 JP2017003746W WO2017135365A1 WO 2017135365 A1 WO2017135365 A1 WO 2017135365A1 JP 2017003746 W JP2017003746 W JP 2017003746W WO 2017135365 A1 WO2017135365 A1 WO 2017135365A1
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WIPO (PCT)
Prior art keywords
mol
liquid crystal
polyester resin
crystal polyester
aromatic liquid
Prior art date
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PCT/JP2017/003746
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English (en)
Japanese (ja)
Inventor
希望 秋山
亮人 川村
正寿 安藤
Original Assignee
Ｊｘエネルギー株式会社
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Publication date
Application filed by Ｊｘエネルギー株式会社 filed Critical Ｊｘエネルギー株式会社
Priority to CN201780006453.7A priority Critical patent/CN108602943B/zh
Publication of WO2017135365A1 publication Critical patent/WO2017135365A1/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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/79—Interfacial processes, i.e. processes involving a reaction at the interface of two non-miscible liquids
    • 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
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones

Definitions

  • the present invention relates to a wholly aromatic liquid crystal polyester resin and a method for producing the same. Furthermore, the present invention relates to a wholly aromatic liquid crystal polyester resin composition containing the wholly aromatic liquid crystal polyester resin, a molded article and an electronic component comprising the composition.
  • the wholly aromatic liquid crystal polyester resin is excellent in moldability, heat resistance, and fillability
  • a molded product for example, an injection molded product
  • the wholly aromatic liquid crystal polyester resin is required to have more excellent filling properties.
  • Patent Document 1 proposes a wholly aromatic liquid crystal polyester resin capable of suppressing the generation of blisters.
  • the inventors of the present invention have now solved the above problem by setting the structural unit contained in the wholly aromatic liquid crystal polyester resin as a specific structural unit and a composition ratio, and setting the melting point of the wholly aromatic liquid crystal polyester resin to 320 ° C. or higher.
  • the knowledge that it can be solved was obtained.
  • the present invention is based on such knowledge.
  • an object of the present invention is to provide a wholly aromatic liquid crystal polyester resin having excellent filling properties, blister resistance and low warpage while maintaining physical properties such as mechanical strength.
  • the wholly aromatic liquid crystal polyester resin according to the present invention is A wholly aromatic liquid crystal polyester resin comprising structural units (I) to (V) represented by the following formulas (I) to (V):
  • the melting point is 320 ° C. or higher.
  • the content of the structural unit (III) is preferably at least twice the content of the structural unit (IV).
  • the method for producing the wholly aromatic liquid crystal polyester resin according to the present invention is as follows. It comprises a step of polymerizing monomers represented by the following formulas (1) to (5).
  • the monomer polymerization step is carried out in the presence of 1.05 to 1.15 molar equivalents of acetic anhydride with respect to the total hydroxyl groups of the monomers represented by the above formulas (1) to (4).
  • the method comprises melt polymerization of the monomers represented by (1) to (5).
  • a wholly aromatic liquid crystal polyester resin composition according to the present invention is characterized by comprising the above wholly aromatic liquid crystal polyester resin and an inorganic filler.
  • the inorganic filler is preferably a fibrous filler or a plate-like filler.
  • content of a fibrous filler and a plate-shaped filler is 100 weight part or less in total with respect to 100 weight part of wholly aromatic liquid crystal polyester resins contained in a wholly aromatic liquid crystal polyester resin composition. It is preferable.
  • the molded product according to the present invention is characterized by comprising the wholly aromatic liquid crystal polyester resin composition.
  • An electronic component according to the present invention includes the wholly aromatic liquid crystal polyester resin composition.
  • the present invention since it has high mechanical strength, filling property and blister resistance, it is possible to produce a molded product having a very thin wall thickness portion, and to achieve high integration, thinning, and low profile of electronic components. Can be realized. Further, according to the present invention, it is possible to prevent warping.
  • the wholly aromatic liquid crystalline polyester resin according to the present invention comprises structural units (I) to (V) represented by the following formulas (I) to (V), and the structural units (I) to (V) in the aromatic liquid crystalline polyester are:
  • the composition ratio (mol%) of (V) satisfies the following conditions. According to such a wholly aromatic liquid crystal polyester resin, high mechanical strength, filling property, blister resistance and low warpage can be imparted to a molded product produced using the resin.
  • the blending ratio (mol%) between the structural unit (III) and the structural unit (IV) in the wholly aromatic liquid crystal polyester resin is such that the content of the structural unit (III) is twice the content of the structural unit (IV). It is preferable that the number is 4 times or more.
  • the melting point of the wholly aromatic liquid crystal polyester resin according to the present invention is 320 ° C. or higher. Since the wholly aromatic liquid crystal polyester resin according to the present invention has a high melting point, it can satisfy heat resistance required for an electronic component.
  • the melting point is based on ISO11357-3 and ASTM D3418, and can be measured by using, for example, a differential scanning calorimeter (DSC) manufactured by Seiko Denshi Kogyo Co., Ltd.
  • DSC differential scanning calorimeter
  • the temperature was raised from room temperature to 380 ° C. at a rate of temperature increase of 20 ° C./min, and after the wholly aromatic liquid crystal polyester resin was completely melted, the temperature was decreased to 50 ° C. at a rate of 10 ° C./min, and further 20 ° C./min.
  • the peak of the endothermic peak obtained when the temperature is raised to 420 ° C. at a rate of is defined as the melting point.
  • the wholly aromatic liquid crystal polyester resin comprises the above-described structural unit (I), and the composition ratio (mol%) of the structural unit (I) in the aromatic liquid crystal polyester is 15 mol% to 35 mol%. It is. More preferably, it is 20 mol% to 35 mol%, and further preferably 25 mol% to 35 mol%.
  • Examples of the monomer that provides the structural unit (I) include p-hydroxybenzoic acid (HBA, the following formula (1)), acylated products, ester derivatives, acid halides, and the like.
  • HBA p-hydroxybenzoic acid
  • the wholly aromatic liquid crystal polyester resin comprises the above-described structural unit (II), and the composition ratio (mol%) of the structural unit (II) in the aromatic liquid crystal polyester is 5 mol% to 15 mol%. It is. More preferably, it is 8 mol% to 15 mol%, and still more preferably 8 mol% to 10 mol%.
  • Examples of the monomer that provides the structural unit (II) include 6-hydroxy-2-naphthoic acid (HNA, the following formula (2)), acylated products, ester derivatives, and acid halides.
  • HNA 6-hydroxy-2-naphthoic acid
  • the wholly aromatic liquid crystal polyester resin comprises the above-described structural unit (III), and the composition ratio (mol%) of the structural unit (III) in the aromatic liquid crystal polyester is 21 mol% to 29 mol%. It is. More preferably, it is 21 mol% to 28 mol%, and further preferably 22 mol% to 26 mol%.
  • Examples of the monomer that provides the structural unit (III) include hydroquinone (HQ, the following formula (3)), acylated products thereof, and the like.
  • the wholly aromatic liquid crystal polyester resin comprises the above-described structural unit (IV), and the composition ratio (mol%) of the structural unit (IV) in the aromatic liquid crystal polyester is 1 mol% to 9 mol%. It is. More preferably, it is 1.5 mol% to 9 mol%, and still more preferably 1.5 mol% to 7 mol%.
  • Examples of the monomer that gives the structural unit (IV) include 4,4-dihydroxybiphenyl (BP, the following formula (4)), acylated products thereof, and the like.
  • the wholly aromatic liquid crystal polyester resin comprises the above-described structural unit (V), and the composition ratio (mol%) of the structural unit (V) in the aromatic liquid crystal polyester is 25 mol% to 40 mol%. It is. More preferably, it is 25 mol% to 35 mol%, and further preferably 27.5 mol% to 32.5 mol%.
  • Examples of the monomer that gives the structural unit (V) include terephthalic acid (TPA, the following formula (5)), ester derivatives thereof, and acid halides.
  • the wholly aromatic liquid crystal polyester resin according to the present invention can be produced by polymerizing monomers represented by the above formulas (1) to (5) by a conventionally known method.
  • the wholly aromatic liquid crystal polyester resin according to the present invention can be produced only by melt polymerization. It can also be produced by preparing a prepolymer by melt polymerization and further solid-phase polymerizing it.
  • the monomers represented by the above formulas (1) to (5) are combined in a predetermined blending amount to 100 mol%, and the above formula is used. It is preferable to carry out the reaction under reflux of acetic acid in the presence of 1.05 to 1.15 molar equivalents of acetic anhydride, based on the total hydroxyl groups of the monomers represented by (1) to (4).
  • the prepolymer obtained by melt polymerization is cooled and solidified and then pulverized into powder or flakes, and then a known solid phase polymerization method is used.
  • a method of heat-treating the prepolymer resin for 1 to 30 hours in a temperature range of 200 to 350 ° C. in an inert atmosphere such as nitrogen or in a vacuum is preferably selected.
  • the solid phase polymerization may be performed with stirring, or may be performed in a standing state without stirring.
  • a catalyst may be used or may not be used.
  • the catalyst to be used those conventionally known as polyester polymerization catalysts can be used, and metals such as magnesium acetate, stannous acetate, tetrabutyl titanate, lead acetate, sodium acetate, potassium acetate, and antimony trioxide are used. Examples thereof include salt catalysts, nitrogen-containing heterocyclic compounds such as N-methylimidazole, and organic compound catalysts.
  • the amount of the catalyst used is not particularly limited, but is preferably 0.0001 to 0.1 parts by weight with respect to 100 parts by weight of the total amount of monomers.
  • the polymerization reaction apparatus in melt polymerization is not particularly limited, but a reaction apparatus used for reaction of a general high viscosity fluid is preferably used.
  • reaction apparatuses include, for example, a stirring tank type polymerization reaction apparatus having a stirrer having various types of stirrer blades, a vertical type, a multistage type, a spiral band type, a helical shaft type, or the like, or And a kneader, a roll mill, a Banbury mixer, and the like, which are generally used for resin kneading.
  • the wholly aromatic liquid crystal polyester resin composition according to the present invention comprises the above wholly aromatic liquid crystal polyester resin and an inorganic filler.
  • the content of the wholly aromatic liquid crystal polyester resin in the wholly aromatic liquid crystal polyester resin composition is preferably 50% by weight or more, and more preferably 60 to 90% by weight.
  • an inorganic filler contained in a wholly aromatic liquid crystal polyester resin composition for example, fibrous, plate-like or powdery ones can be used, and these may be used in combination. Especially, it is preferable to use together a fibrous filler and a plate-shaped filler.
  • the inorganic filler include glass fiber, milled glass, silica alumina fiber, alumina fiber, carbon fiber, aramid fiber, potassium titanate whisker, aluminum borate whisker, wollastonite, talc, mica, graphite, calcium carbonate, Examples thereof include dolomite, clay, glass flakes, glass beads, barium sulfate and titanium oxide, and the wholly aromatic liquid crystal polyester resin composition may contain one or more of these.
  • the content of the inorganic filler in the wholly aromatic liquid crystal polyester resin composition is preferably 100 parts by weight or less with respect to 100 parts by weight of the wholly aromatic liquid crystal polyester resin contained in the wholly aromatic liquid crystal polyester resin composition. More preferred is 10 to 65 parts by weight.
  • the wholly aromatic liquid crystal polyester resin composition according to the present invention may contain a resin other than the wholly aromatic liquid crystal polyester resin as long as the effects of the present invention are not impaired.
  • a resin other than the wholly aromatic liquid crystal polyester resin for example, polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyarylate, polyamide, polyimide, polyethersulfone, polyetheretherketone, polyphenylene sulfide, polytetrafluoroethylene and the like, and wholly aromatic liquid crystal polyester resin composition is One or more of these may be included.
  • the wholly aromatic liquid crystal polyester resin composition according to the present invention has other additives such as a colorant, a dispersant, a plasticizer, an antioxidant, a flame retardant, a heat stabilizer, as long as the effects of the present invention are not impaired.
  • a colorant such as a colorant, a dispersant, a plasticizer, an antioxidant, a flame retardant, a heat stabilizer, as long as the effects of the present invention are not impaired.
  • An ultraviolet absorber, an antistatic agent, and a surfactant may be included.
  • a wholly aromatic liquid crystal polyester resin composition is obtained by melt-kneading a wholly aromatic liquid crystal polyester resin with a filler and the like using a Banbury mixer, kneader, single screw or twin screw extruder, etc. Can do.
  • the molded article according to the present invention comprises a wholly aromatic liquid crystal polyester resin composition, and can be obtained by injection molding or extrusion molding the composition.
  • seat, and nonwoven fabric which consist of a wholly aromatic liquid crystal polyester resin composition can be obtained by the same method.
  • Specific film forming methods include inflation molding, melt extrusion molding, solution cast molding, and the like.
  • the film thus obtained may be a single layer film made of a wholly aromatic polyester resin composition or a multilayer film with different materials.
  • a film formed by melt extrusion molding or solution casting may be stretched uniaxially or biaxially. Moreover, you may heat-process in order to remove the anisotropy of these films.
  • the electronic component according to the present invention comprises the wholly aromatic liquid crystal polyester resin composition.
  • Electronic components include secondary connectors such as high-speed transmission connectors, CPU sockets, circuit boards, flexible circuit boards, laminated circuit boards, anti-collision radars, RFID tags, capacitors, inverter parts, insulating films, lithium ion batteries, etc. Examples include battery insulation materials and speaker diaphragms.
  • these electronic components include a molded product (for example, an injection molded product) or a film made of a wholly aromatic liquid crystal polyester resin composition.
  • Example 1 wholly aromatic liquid crystal polyester resin A
  • HBA p-hydroxybenzoic acid
  • HNA 6-hydroxy-2-naphthoic acid
  • HQ hydroquinone
  • 9 g (24 mol%), 4,4-dihydroxybiphenyl (BP) 6.7 g (6 mol%), terephthalic acid (TPA) 29.9 (30 mol%) were added, and potassium acetate and magnesium acetate were added as catalysts.
  • the polymerization vessel in acetic acid distillation was heated at 0.5 ° C./min, and when the melt temperature in the tank reached 310 ° C., the polymer was taken out and cooled and solidified.
  • the obtained polymer was pulverized and pulverized to a size passing through a sieve having an aperture of 1.0 mm to obtain a prepolymer.
  • the prepolymer obtained above is filled into a glass tube oven manufactured by Shibata Kagaku, and the heater temperature is raised from room temperature to 290 ° C. over 12 hours while rotating, and then the temperature is maintained at 290 ° C. for 1 hour.
  • the solid phase polymerization was performed. Thereafter, natural heat was radiated at room temperature while rotating the tank to obtain a wholly aromatic liquid crystal polyester resin A.
  • a polarizing microscope BH-2 manufactured by Olympus Corporation equipped with a hot stage FP82HT for microscopes manufactured by METTLER a polyester sample was heated and melted on a microscope heating stage, and liquid crystallinity was confirmed from the presence or absence of optical anisotropy. .
  • Example 2 Totally aromatic liquid crystal polyester resin B
  • a liquid crystal polyester resin B was obtained in the same manner as in Example 1 except that the monomer charge was changed to 30 mol% HBA, 15 mol% HNA, 26 mol% HQ, 1.5 mol% BP, and 27.5 mol% TPA. Similarly, liquid crystal properties were confirmed.
  • Example 3 Totally aromatic liquid crystal polyester resin C
  • a liquid crystal polyester resin C was obtained in the same manner as in Example 1 except that the monomer charge was changed to 30 mol% HBA, 10 mol% HNA, 21 mol% HQ, 9 mol% BP, and 30 mol% TPA. The sex was confirmed.
  • Example 4 Totally aromatic liquid crystal polyester resin D
  • a liquid crystal polyester resin D was obtained in the same manner as in Example 1 except that the monomer charge was changed to 30 mol% HBA, 10 mol% HNA, 25 mol% HQ, 5 mol% BP, and 30 mol% TPA. The sex was confirmed.
  • the prepolymer obtained above was filled into a glass tube oven made by Shibata Kagaku, and when it was attempted to polymerize to the desired molecular weight by solid phase polymerization, the prepolymer melted, and further solid phase polymerization was performed. could not be implemented. Then, natural heat was radiated at room temperature while rotating the tank, and a liquid crystal polyester resin E was obtained.
  • Extractability >> After the temperature of the polymerization container reached a predetermined temperature, the behavior when the polymer was extracted from the polymerization container was observed, and the extractability was evaluated according to the following evaluation criteria. (Evaluation criteria) ⁇ : Can be easily extracted. X: Extraction was difficult and resin remained in the container.
  • a wholly aromatic liquid crystal polyester resin A was obtained. 7 parts by weight of a fibrous filler (manufactured by Central Glass Fiber Co., Ltd., trade name: EFH150-01) and 100 parts by weight of a plate-like filler (100 parts by weight of the wholly aromatic liquid crystalline polyester resin A obtained as described above.
  • mice manufactured by Yamaguchi Mica Co., Ltd., trade name: AB-25S, 36 parts by weight and carbon black (manufactured by Cabot Co., Ltd., trade name: REGAL99I) were blended and melted in a twin screw extruder. The kneaded product was pelletized to obtain a wholly aromatic liquid crystal polyester resin composition A. Further, a wholly aromatic liquid crystal polyester resin composition H was obtained in the same manner except that the wholly aromatic liquid crystal polyester resin A was changed to the wholly aromatic liquid crystal polyester resin H obtained in Comparative Example 4.
  • the filling property of the resin composition was evaluated based on the length of the thin part formed by flowing the composition into the thin part. This test was repeated 20 times, and the average length of the formed thin portions was shown in Table 2. A similar test was performed on the wholly aromatic liquid crystal polyester resin composition H, and the results are shown in Table 2.

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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)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Le problème décrit par la présente invention est de produire une résine de polyester à cristaux liquides entièrement aromatique présentant une résistance mécanique élevée, d'excellentes propriétés de remplissage, résistance au boursouflage, et un faible gauchissement. La solution selon l'invention concerne une résine de polyester à cristaux liquides entièrement aromatique comprenant des motifs structurels (I) à (V), qui sont représentés par les formules (I) à (V), et est caractérisée en ce que : les rapports de composition (% en mole) des motifs structurels (I) à (V) ci-inclus sont de 15 % en mole ≤ motif structurel (I) ≤ 35 % en mole, 5 % en mole ≤ motif structurel (II) ≤ 15 % en mole, 21 % en mole ≤ motif structurel (III) ≤ 29 % en mole, 1 % en mole ≤ motif structurel (IV) ≤ 9 % en mole, et 25 % en mole ≤ motif structurel (V) ≤ 40 % en mole, où les motifs structurels (I) à (V) totalisent 100 % en mole ; et le point de fusion est d'au moins 320 °C.
PCT/JP2017/003746 2016-02-04 2017-02-02 Résine de polyester à cristaux liquides entièrement aromatique et son procédé de production WO2017135365A1 (fr)

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CN201780006453.7A CN108602943B (zh) 2016-02-04 2017-02-02 全芳香族液晶聚酯树脂及其制造方法

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JP2016020161A JP6626358B2 (ja) 2016-02-04 2016-02-04 全芳香族液晶ポリエステル樹脂およびその製造方法
JP2016-020161 2016-02-04

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Cited By (1)

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US20210269588A1 (en) * 2018-06-26 2021-09-02 Eneos Corporation Resin molded article comprising wholly aromatic liquid crystalline polyester resin capable of reducing dielectric loss tangent by heat treatment and electrical and electronic component

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JP7194586B2 (ja) * 2018-12-27 2022-12-22 Ｅｎｅｏｓ株式会社 液晶ポリマーおよび該液晶ポリマーを含む樹脂組成物からなる樹脂成形品
JP6745008B1 (ja) 2019-05-17 2020-08-19 住友化学株式会社 液晶ポリエステル樹脂組成物のペレット
JP6675028B1 (ja) 2019-05-17 2020-04-01 住友化学株式会社 液晶ポリエステル樹脂組成物のペレット及び液晶ポリエステル樹脂組成物のペレットの製造方法
JP7284033B2 (ja) 2019-08-07 2023-05-30 上野製薬株式会社 液晶ポリエステル樹脂
US12142820B2 (en) 2019-09-10 2024-11-12 Ticona Llc 5G system containing a polymer composition
US12209164B2 (en) 2019-09-10 2025-01-28 Ticona Llc Polymer composition and film for use in 5G applications
US11917753B2 (en) 2019-09-23 2024-02-27 Ticona Llc Circuit board for use at 5G frequencies
WO2022210967A1 (fr) * 2021-03-30 2022-10-06 ポリプラスチックス株式会社 Polyester entièrement aromatique et composition de résine de polyester
EP4509543A1 (fr) 2022-04-11 2025-02-19 Toray Industries, Inc. Résine de polyester à cristaux liquides, composition de résine de polyester à cristaux liquides et produit moulé la comprenant

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Publication number Priority date Publication date Assignee Title
US20210269588A1 (en) * 2018-06-26 2021-09-02 Eneos Corporation Resin molded article comprising wholly aromatic liquid crystalline polyester resin capable of reducing dielectric loss tangent by heat treatment and electrical and electronic component
US11505647B2 (en) * 2018-06-26 2022-11-22 Eneos Corporation Resin molded article comprising wholly aromatic liquid crystalline polyester resin capable of reducing dielectric loss tangent by heat treatment and electrical and electronic component

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