WO2024143334A1 - 液晶性樹脂組成物及びそれを用いたコネクター - Google Patents

液晶性樹脂組成物及びそれを用いたコネクター Download PDF

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Publication number
WO2024143334A1
WO2024143334A1 PCT/JP2023/046579 JP2023046579W WO2024143334A1 WO 2024143334 A1 WO2024143334 A1 WO 2024143334A1 JP 2023046579 W JP2023046579 W JP 2023046579W WO 2024143334 A1 WO2024143334 A1 WO 2024143334A1
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Prior art keywords
resin composition
liquid crystal
crystal resin
mass
liquid crystalline
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Ceased
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PCT/JP2023/046579
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English (en)
French (fr)
Japanese (ja)
Inventor
真奈 中村
昭宏 長永
峰生 大竹
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Polyplastics Co Ltd
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Polyplastics Co Ltd
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Priority to JP2024567840A priority Critical patent/JPWO2024143334A1/ja
Priority to CN202380088990.6A priority patent/CN120435520A/zh
Publication of WO2024143334A1 publication Critical patent/WO2024143334A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • 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

Definitions

  • the present invention has been made to solve the above problems, and its purpose is to provide a liquid crystalline resin composition with good flowability and releasability that gives a molded article with excellent mechanical strength and suppressed blistering, and a connector using the same.
  • the liquid crystalline resin composition has a content of the plate-like filler (E) of 5 to 15% by mass based on the entire liquid crystalline resin composition.
  • a molded article comprising a liquid crystal resin composition according to any one of (1) to (5).
  • FIG. 1(a) is a perspective view showing a U-shaped liquid crystalline resin molding used in the evaluation of releasability carried out in the examples
  • FIG. 1(b) is a side view showing the U-shaped liquid crystalline resin molding.
  • the liquid crystal resin composition of the present invention contains (A) a liquid crystal resin, (B) whiskers, (C) an epoxy group-containing olefin polymer, and (D) a polyhydric alcohol fatty acid ester.
  • the liquid crystal resin (A) used in the present invention refers to a melt-processable polymer having the property of being capable of forming an optically anisotropic molten phase.
  • the property of the anisotropic molten phase can be confirmed by a conventional polarized light inspection method using crossed polarizers. More specifically, the anisotropic molten phase can be confirmed by observing a molten sample placed on a Leitz hot stage at a magnification of 40 times under a nitrogen atmosphere using a Leitz polarizing microscope.
  • the liquid crystal polymer applicable to the present invention is inspected between crossed polarizers, it usually transmits polarized light even in a molten stationary state, and is optically anisotropic.
  • the type of liquid crystal resin (A) as described above is not particularly limited, but is preferably an aromatic polyester and/or an aromatic polyester amide. Polyesters that partially contain aromatic polyesters and/or aromatic polyester amides in the same molecular chain are also included in this range.
  • the liquid crystal resin (A) one that has an inherent viscosity (I.V.) of preferably at least about 2.0 dl/g, and more preferably 2.0 to 10.0 dl/g when dissolved in pentafluorophenol at a concentration of 0.1% by mass at 60°C is preferably used.
  • the aromatic polyester or aromatic polyesteramide as the liquid crystal resin (A) applicable to the present invention is particularly preferably an aromatic polyester or aromatic polyesteramide having as a constituent component a constituent unit derived from at least one selected from the group consisting of aromatic hydroxycarboxylic acids and derivatives thereof.
  • the content of the constituent units derived from at least one selected from the group consisting of aromatic hydroxycarboxylic acids and their derivatives is preferably 45 mol% or more, more preferably 50 mol% or more, even more preferably 55 mol% or more, even more preferably 60 mol% or more, and particularly preferably 62 mol% or more, based on all the constituent units, from the viewpoint of suppressing fluctuations in the molecular structure of (A) liquid crystal resin.
  • the upper limit of the content is not particularly limited, and may be 100 mol% or less, 90 mol% or less, 80 mol% or less, 75 mol% or less, or 70 mol% or less, based on all the constituent units.
  • aromatic hydroxycarboxylic acids such as 4-hydroxybenzoic acid and 6-hydroxy-2-naphthoic acid
  • aromatic diols such as 2,6-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 4,4'-dihydroxybiphenyl, hydroquinone, resorcin, compounds represented by the following general formula (I) and compounds represented by the following general formula (II)
  • aromatic dicarboxylic acids such as 1,4-phenylenedicarboxylic acid, 1,3-phenylenedicarboxylic acid, 4,4'-diphenyldicarboxylic acid, 2,6-naphthalenedicarboxylic acid and compounds represented by the following general formula (III); aromatic amines such as p-aminophenol, p-phenylenediamine and N-acetyl-p-aminophenol.
  • aromatic hydroxycarboxylic acid and its derivatives 4-hydroxybenzoic acid, 6-hydroxy-2-naphthoic acid, or a combination thereof are preferred from the viewpoints of reactivity and stability of the molecular structure of the liquid crystal resin (A).
  • X is a group selected from alkylene (C 1 to C 4 ), alkylidene, —O—, —SO—, —SO 2 —, —S—, and —CO—.
  • the liquid crystal resin (A) used in the present invention can be prepared by a known method using direct polymerization or transesterification from the above monomer compound (or mixture of monomers). Usually, melt polymerization, solution polymerization, slurry polymerization, solid-phase polymerization, or a combination of two or more of these methods is used, and melt polymerization or a combination of melt polymerization and solid-phase polymerization is preferably used.
  • melt polymerization, solution polymerization, slurry polymerization, solid-phase polymerization, or a combination of two or more of these methods is used, and melt polymerization or a combination of melt polymerization and solid-phase polymerization is preferably used.
  • the above compounds capable of forming esters may be used in the polymerization as they are, or may be modified from a precursor to a derivative capable of forming the ester at a stage prior to polymerization.
  • catalysts can be used in these polymerizations, and representative examples include metal salt catalysts such as potassium acetate, magnesium acetate, stannous acetate, tetrabutyl titanate, lead acetate, sodium acetate, antimony trioxide, and tris(2,4-pentanedionato)cobalt(III), and organic compound catalysts such as 1-methylimidazole and 4-dimethylaminopyridine.
  • the amount of catalyst used is generally about 0.001 to 1% by mass, and preferably about 0.01 to 0.2% by mass, based on the total mass of the monomers. If necessary, the molecular weight of the polymer produced by these polymerization methods can be further increased by solid-phase polymerization, in which the polymer is heated under reduced pressure or in an inert gas.
  • the melt viscosity of the liquid crystal resin (A) obtained by the above method is not particularly limited.
  • a resin having a melt viscosity at the molding temperature of 3 Pa ⁇ s to 500 Pa ⁇ s at a shear rate of 1000 sec -1 can be used.
  • a resin having a viscosity that is too high is not preferred because it significantly deteriorates the flowability.
  • the liquid crystal resin (A) may be a mixture of two or more kinds of liquid crystal resins.
  • the fiber diameter of the (B) whiskers is preferably 0.2 to 15 ⁇ m or less, and more preferably 0.25 to 10 ⁇ m. When the fiber diameter is within the above range, the mechanical strength of the molded body is more likely to be improved.
  • the fiber diameter of the (B) whiskers is determined by observing the whiskers with a scanning electron microscope and measuring the fiber diameter of 30 whiskers, and the average of these values is used. The fiber diameter of the (B) whiskers in the liquid crystalline resin composition is measured by applying the above method to the whiskers remaining after the liquid crystalline resin composition is heated at 600°C for 2 hours to incinerate the composition.
  • the aspect ratio of the whiskers i.e., the value of the average fiber length/fiber diameter, is preferably 8 or more, more preferably 10 to 100, and even more preferably 15 to 75, from the viewpoint of the mechanical strength of a molded article such as a connector that contains the liquid crystalline resin composition according to the present invention.
  • the liquid crystal resin composition of the present invention contains an epoxy group-containing olefin polymer (C).
  • the liquid crystal resin composition of the present invention tends to have a well-balanced and excellent mechanical strength and blister resistance while maintaining the excellent mold releasability of the liquid crystal resin composition of the present invention.
  • epoxy group-containing olefin polymers include copolymers composed of repeating units derived from ⁇ -olefins and repeating units derived from glycidyl esters of ⁇ , ⁇ -unsaturated acids.
  • the epoxy group-containing olefin polymers may be used alone or in combination of two or more types.
  • the ⁇ -olefin is not particularly limited, and examples thereof include ethylene, propylene, butene, among which ethylene is preferably used.
  • the glycidyl ester of an ⁇ , ⁇ -unsaturated acid is represented by the following general formula (IV).
  • R' represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a group represented by -R 1 -COOH, and R 1 represents an alkylene group having 1 to 5 carbon atoms.
  • the content of repeating units derived from ⁇ -olefin is preferably 87 to 98% by mass, and the content of repeating units derived from glycidyl ester of ⁇ , ⁇ -unsaturated acid is preferably 13 to 2% by mass.
  • the epoxy group-containing olefin polymer may contain, in addition to the above two components, a third component of repeating units derived from one or more olefin-based unsaturated monomers such as acrylonitrile, acrylic acid esters, methacrylic acid esters, ⁇ -methylstyrene, maleic anhydride, etc., in an amount of 0 to 48 parts by mass per 100 parts by mass of the above two components, as long as it does not impair the present invention.
  • a third component of repeating units derived from one or more olefin-based unsaturated monomers such as acrylonitrile, acrylic acid esters, methacrylic acid esters, ⁇ -methylstyrene, maleic anhydride, etc.
  • Epoxy group-containing olefin polymers can be easily prepared by a normal radical polymerization method using monomers corresponding to each component and a radical polymerization catalyst. More specifically, they can usually be produced by a method in which an ⁇ -olefin and a glycidyl ester of an ⁇ , ⁇ -unsaturated acid are copolymerized in the presence of a radical generator at 500 to 4000 atmospheres and 100 to 300°C in the presence or absence of a suitable solvent or chain transfer agent.
  • the liquid crystal resin composition according to the present invention contains (D) a polyhydric alcohol fatty acid ester.
  • the mold releasability of the liquid crystal resin composition is likely to be improved, and the molded article is likely to have excellent mechanical strength and blister resistance.
  • the (D) polyhydric alcohol fatty acid ester may be used alone or in combination of two or more.
  • a polyhydric alcohol is a compound having two or more alcoholic hydroxyl groups in the molecule.
  • the polyhydric alcohol is preferably a polyhydric alcohol having 3 to 32 carbon atoms.
  • Examples of the polyhydric alcohol include polyglycerols such as glycerin, diglycerin, and decaglycerin; pentaerythritol; dipentaerythritol; diethylene glycol; and propylene glycol.
  • the polyhydric alcohol may be used alone or in combination of two or more. In terms of the heat resistance of the resulting polyhydric alcohol fatty acid ester, pentaerythritol and dipentaerythritol are particularly preferred as polyhydric alcohols.
  • the content of the plate-like filler (E) is preferably 5 to 15 mass% relative to the entire liquid crystal resin composition of the present invention. When the content of the plate-like filler (E) is within the above range, it is easier to obtain a molded article with suppressed anisotropy from the resulting composition while maintaining excellent mechanical strength.
  • the content of the plate-like filler (E) is more preferably 6 to 13 mass%, and even more preferably 8 to 12 mass%.
  • the talc usable in the present invention preferably has a total content of Fe2O3 , Al2O3 and CaO of 2.5 % by mass or less, a total content of Fe2O3 and Al2O3 of more than 1.0% by mass and 2.0 % by mass or less, and a CaO content of less than 0.5% by mass , relative to the total solid content of the talc. That is, the talc usable in the present invention may contain at least one of Fe2O3 , Al2O3 and CaO in addition to SiO2 and MgO as the main components, and each component may be contained within the above content range.
  • Mica is a pulverized silicate mineral containing aluminum, potassium, magnesium, sodium, iron, etc.
  • Examples of mica that can be used in the present invention include muscovite, phlogopite, biotite, and artificial mica, among which muscovite is preferred because of its good hue and low cost.
  • wet grinding and dry grinding are known as methods for grinding minerals.
  • mica raw ore is coarsely ground in a dry grinder, water is added to the slurry, and the resulting material is then wet-ground and dehydrated.
  • the dry grinding method is a common method with low cost, but the wet grinding method makes it easier to grind minerals thinly and finely.
  • it is preferable to use thin and finely ground material because it can obtain mica having the above-mentioned median diameter and the preferred thickness described below. Therefore, in the present invention, it is preferable to use mica produced by the wet grinding method.
  • a step of dispersing the ground material in water is necessary, so that in order to increase the dispersion efficiency of the ground material, it is common to add a flocculating sedimentation agent and/or a sedimentation aid to the ground material.
  • flocculating sedimentation agents and sedimentation aids examples include polyaluminum chloride, aluminum sulfate, ferrous sulfate, ferric sulfate, copper chloride, polyferric sulfate, polyferric chloride, iron-silica inorganic polymer flocculant, ferric chloride-silica inorganic polymer flocculant, hydrated lime (Ca(OH) 2 ), caustic soda (NaOH), soda ash (Na 2 CO 3 ), etc.
  • These flocculating sedimentation agents and sedimentation aids have an alkaline or acidic pH.
  • the mica used in the present invention is preferably one that does not use a flocculating sedimentation agent and/or a sedimentation aid when wet grinding.
  • a flocculating sedimentation agent and/or a sedimentation aid when used, decomposition of the polymer in the liquid crystalline resin composition is unlikely to occur, and large amounts of gas are unlikely to be generated, or a decrease in the molecular weight of the polymer is unlikely to occur, making it easier to maintain the performance of the resulting molded article better.
  • the thickness of the mica that can be used in the present invention is preferably 0.01 to 1 ⁇ m, and particularly preferably 0.03 to 0.3 ⁇ m, as measured by observation under an electron microscope. If the thickness of the mica is 0.01 ⁇ m or more, the mica is less likely to crack during melt processing of the liquid crystalline resin composition, which is preferable since it may be easier to improve the rigidity of the molded article. If the thickness of the mica is 1 ⁇ m or less, the effect of improving the rigidity of the molded article is likely to be sufficient, which is preferable.
  • the mica that can be used in the present invention may be surface-treated with a silane coupling agent or the like, and/or may be granulated with a binder to form granules.
  • liquid crystal resin composition of the present invention other polymers, other fillers, other release agents, and known substances generally added to synthetic resins, i.e., stabilizers such as antioxidants and ultraviolet absorbers, antistatic agents, flame retardants, colorants such as dyes and pigments, lubricants, crystallization accelerators, crystal nucleating agents, etc., may be appropriately added depending on the required performance, within a range that does not impair the effects of the present invention.
  • Epoxy group-containing styrene polymers include known epoxy group-containing styrene polymers, including copolymers composed of repeating units derived from styrenes and repeating units derived from glycidyl esters of ⁇ , ⁇ -unsaturated acids.
  • Epoxy group-free olefin polymers include, for example, polyethylene, polypropylene, polybutene, ethylene-propylene copolymers, ethylene-butene copolymers, ethylene-octene copolymers, polybutadiene, polyisoprene, polychloroprene, ethylene-propylene-butadiene copolymers, ethylene-propylene-isoprene copolymers, ethylene-propylene-chloroprene copolymers, ethylene-ethyl acrylate copolymers, ethylene-vinyl acetate copolymers, etc.
  • the other fillers refer to fillers other than (B) whiskers and (E) plate-like fillers, and examples thereof include (C) granular fillers such as silica; fibrous fillers other than (B) whiskers, such as glass fiber; and carbon black. Since the effect of suppressing nap formation on the surface of the molded product is likely to be high, it is preferable that the liquid crystalline resin composition of the present invention does not contain fibrous fillers other than (B) whiskers, such as glass fiber.
  • the other release agent refers to a release agent other than the polyhydric alcohol fatty acid ester (D), and examples thereof include fatty acid metal salts such as calcium stearate, fatty acid amides, low molecular weight polyolefins, and the like. Since a molded article having improved blister resistance while maintaining superior mechanical strength and superior release properties can be easily obtained from the liquid crystal resin composition of the present invention, it is preferable that the liquid crystal resin composition of the present invention does not contain a release agent other than the polyhydric alcohol fatty acid ester (D), for example, a fatty acid metal salt such as calcium stearate.
  • a release agent other than the polyhydric alcohol fatty acid ester (D) for example, a fatty acid metal salt such as calcium stearate.
  • the preparation of the resin composition of the present invention is not particularly limited.
  • the above-mentioned (A) component, (B) component, (C) component, (D) component, optionally (E) component, and optionally other components are mixed, and melt-kneaded using a single-screw or twin-screw extruder to prepare a liquid crystal resin composition.
  • Aromatic polyester amide The following raw materials were charged into a polymerization vessel, and the temperature of the reaction system was raised to 140°C and reacted at 140°C for 1 hour. Thereafter, the temperature was further raised to 340°C over 4.5 hours, and the pressure was reduced to 10 Torr (i.e., 1330 Pa) over 15 minutes, and melt polymerization was carried out while distilling out acetic acid, excess acetic anhydride, and other low boiling points.

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Connector Housings Or Holding Contact Members (AREA)
PCT/JP2023/046579 2022-12-26 2023-12-26 液晶性樹脂組成物及びそれを用いたコネクター Ceased WO2024143334A1 (ja)

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CN202380088990.6A CN120435520A (zh) 2022-12-26 2023-12-26 液晶性树脂组合物和使用了其的连接器

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017193704A (ja) * 2016-04-15 2017-10-26 東レ株式会社 液晶ポリエステル樹脂組成物およびそれからなる成形品
WO2019124256A1 (ja) * 2017-12-18 2019-06-27 住友化学株式会社 液晶ポリエステル組成物および成形体
JP2020007394A (ja) * 2018-07-03 2020-01-16 ポリプラスチックス株式会社 耐摺動摩耗部材用液晶性樹脂組成物及びそれを用いた耐摺動摩耗部材
JP2021055059A (ja) * 2019-09-30 2021-04-08 ポリプラスチックス株式会社 樹脂組成物及びこれを用いたコネクタ部品
JP2021167408A (ja) * 2020-04-08 2021-10-21 ポリプラスチックス株式会社 樹脂組成物及びその成形品
WO2022004553A1 (ja) * 2020-06-30 2022-01-06 ポリプラスチックス株式会社 耐ボールベアリング摺動摩耗部材用液晶性樹脂組成物及びそれを用いた耐ボールベアリング摺動摩耗部材

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017193704A (ja) * 2016-04-15 2017-10-26 東レ株式会社 液晶ポリエステル樹脂組成物およびそれからなる成形品
WO2019124256A1 (ja) * 2017-12-18 2019-06-27 住友化学株式会社 液晶ポリエステル組成物および成形体
JP2020007394A (ja) * 2018-07-03 2020-01-16 ポリプラスチックス株式会社 耐摺動摩耗部材用液晶性樹脂組成物及びそれを用いた耐摺動摩耗部材
JP2021055059A (ja) * 2019-09-30 2021-04-08 ポリプラスチックス株式会社 樹脂組成物及びこれを用いたコネクタ部品
JP2021167408A (ja) * 2020-04-08 2021-10-21 ポリプラスチックス株式会社 樹脂組成物及びその成形品
WO2022004553A1 (ja) * 2020-06-30 2022-01-06 ポリプラスチックス株式会社 耐ボールベアリング摺動摩耗部材用液晶性樹脂組成物及びそれを用いた耐ボールベアリング摺動摩耗部材

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