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WO2013051346A1 - Polyester entièrement aromatique, composition de résine de polyester et article moulé en polyester - Google Patents

Polyester entièrement aromatique, composition de résine de polyester et article moulé en polyester Download PDF

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Publication number
WO2013051346A1
WO2013051346A1 PCT/JP2012/070927 JP2012070927W WO2013051346A1 WO 2013051346 A1 WO2013051346 A1 WO 2013051346A1 JP 2012070927 W JP2012070927 W JP 2012070927W WO 2013051346 A1 WO2013051346 A1 WO 2013051346A1
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WIPO (PCT)
Prior art keywords
polyester
wholly aromatic
aromatic polyester
mol
structural unit
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2012/070927
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English (en)
Japanese (ja)
Inventor
大輔 依藤
俊明 横田
峰生 大竹
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Polyplastics Co Ltd
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Polyplastics Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Polyplastics Co Ltd filed Critical Polyplastics Co Ltd
Priority to JP2013537452A priority Critical patent/JP6189750B2/ja
Publication of WO2013051346A1 publication Critical patent/WO2013051346A1/fr
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
    • C08G63/605—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 the hydroxy and carboxylic groups being bound to aromatic rings
    • 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
    • C08K5/00—Use of organic ingredients

Definitions

  • the present invention relates to a wholly aromatic polyester, a polyester resin composition, and a polyester molded article.
  • wholly aromatic polyesters using 1,4-phenylenedicarboxylic acid, 1,4-dihydroxybenzene, 4,4'-dihydroxybiphenyl, etc. as copolymerization components are known.
  • the melting point of this wholly aromatic polyester is 350 ° C. or higher, which is too high for melt processing with a general-purpose apparatus.
  • Patent Documents 1 and 2 propose a copolyester in which 6-hydroxy-2-naphthoic acid, a diol component, and a dicarboxylic acid component are combined.
  • the present invention aims to solve the above problems and provide a wholly aromatic polyester excellent in heat resistance and toughness.
  • the wholly aromatic polyester is composed of structural units represented by the following general formulas (I), (II), (III), (IV) and (V).
  • the structural unit is 40 to 70 mol%
  • the structural unit (II) is 7 to 14 mol%
  • the structural unit (III) is 8 to 26.5 mol%
  • the structural unit (IV) is 0 to 10 mol%.
  • the structural unit of (V) is 8 to 26.5 mol% and the total of the structural unit of (II) and the structural unit of (IV) is 12 to 17 mol%, the above problem can be solved.
  • the headline and the present invention were completed. More specifically, the present invention provides the following.
  • the structural unit is 40 to 70 mol%, the structural unit (II) is 7 to 14 mol%, the structural unit (III) is 8 to 26.5 mol%, and the structural unit (IV) is 0 to 10 mol%.
  • (V) is 8 to 26.5 mol%, and the total of the structural unit (II) and the structural unit (IV) is 12 to 17 mol%.
  • a polyester resin composition comprising 120 parts by mass or less of an inorganic filler or an organic filler with respect to 100 parts by mass of the wholly aromatic polyester according to any one of (1) to (4).
  • polyester molded product according to (7) wherein the polyester molded product is a connector, a CPU socket, a relay switch component, a bobbin, an actuator, a noise reduction filter case, or a heat fixing roll of an OA device.
  • the wholly aromatic polyester of the present invention comprising a specific structural unit and exhibiting optical anisotropy at the time of melting, and the polyester resin composition containing the wholly aromatic polyester have fluidity at the time of melting. It is good and has excellent heat resistance and toughness when formed into a molded product.
  • the wholly aromatic polyester or polyester resin composition of the present invention is not so high in molding processing temperature that it can be injection molded, extruded and compressed without using a molding machine having a special structure. .
  • the wholly aromatic polyester or polyester resin composition of the present invention is excellent in moldability and can be molded using various molding machines. As a result, it can be easily applied to various three-dimensional molded products, fibers, films and the like. Can be processed. For this reason, molded articles such as connectors, CPU sockets, relay switch parts, bobbins, actuators, noise reduction filter cases, or heat fixing rolls for OA equipment, which are suitable uses of the wholly aromatic polyester or polyester resin composition of the present invention. Is also easily obtained.
  • the wholly aromatic polyester of the present invention is composed of structural units represented by the following general formulas (I), (II), (III), (IV) and (V).
  • the structural unit represented by the general formula (I) is 4-hydroxybenzoic acid (HBA).
  • HBA 4-hydroxybenzoic acid
  • the wholly aromatic polyester of the present invention contains 40 to 70 mol% of HBA with respect to all the structural units.
  • the content of HBA is less than 40 mol% or more than 70 mol%, the melting point of the wholly aromatic polyester is remarkably increased, and in some cases, the wholly aromatic polyester is solidified in the reactor at the time of production, and a polymer having a desired molecular weight is obtained. Is not preferable because it cannot be produced.
  • the structural unit represented by the general formula (II) is 6-hydroxy-2-naphthoic acid (HNA).
  • the wholly aromatic polyester of the present invention contains 7 to 14 mol% of HNA with respect to all structural units.
  • the content of HNA is less than 7 mol%, the melting point of the oligomer is remarkably increased during the production of the wholly aromatic polyester, and in some cases, the wholly aromatic polyester is solidified in the reactor during the production, and a polymer having a desired molecular weight is obtained. This is not preferable because it cannot be manufactured.
  • the HNA content exceeds 14 mol%, the heat resistance of the wholly aromatic polyester of the present invention is lowered, which is not preferable.
  • the structural unit represented by the general formula (III) is 1,4-phenylenedicarboxylic acid (TA).
  • the wholly aromatic polyester of the present invention contains 8 to 26.5 mol% of TA with respect to all the structural units.
  • the TA content is less than 8 mol% or exceeds 26.5 mol%, the melting point of the wholly aromatic polyester is remarkably increased, and in some cases, the wholly aromatic polyester is solidified in the reactor during production, and the desired molecular weight is obtained. This is not preferable because the polymer cannot be produced.
  • the structural unit represented by the general formula (IV) is 1,3-phenylenedicarboxylic acid (IA).
  • the wholly aromatic polyester of the present invention contains 0 to 10 mol% of IA with respect to all structural units. When the content of IA exceeds 10 mol%, the heat resistance of the wholly aromatic polyester is lowered, which is not preferable.
  • the structural unit represented by the general formula (V) is 1,4-benzenediol (HQ).
  • the wholly aromatic polyester of the present invention contains 8 to 26.5 mol% of HQ with respect to all the structural units.
  • the content of HQ is less than 8 mol% or exceeds 26.5 mol%, the melting point of the wholly aromatic polyester may be extremely high in some cases, and the wholly aromatic polyester is solidified in the reactor at the time of manufacture. This is not preferable because the polymer cannot be produced.
  • the total content of the constituent unit (II) and the constituent unit (IV) is 12 to 17 mol% with respect to all constituent units.
  • the toughness of the polyester molded product formed by molding the wholly aromatic polyester or polyester resin composition of the present invention is not preferable.
  • the heat resistance of a wholly aromatic polyester will become low when the said total content exceeds 17 mol%, it is unpreferable.
  • the wholly aromatic polyester of the present invention contains a specific amount of each of the specific structural units (I) to (V) with respect to the total structural units, and further includes the structural unit of (II) And the total content of the structural units of (IV) are adjusted to a specific range, it has heat resistance, and the toughness of a polyester molded product formed by molding the wholly aromatic polyester of the present invention is also increased.
  • an example of the index representing the toughness is the amount of crystallization heat of the wholly aromatic polyester.
  • the amount of heat of crystallization is 2.7 J / g or more, the toughness tends to decrease, which is not preferable.
  • the preferable value of the amount of crystallization heat is 2.5 J / g or less, more preferably 2.2 J / g or less. This amount of crystallization can be determined by differential calorimetry.
  • heat amount of a polyester resin composition is considered. In the case of the polyester resin composition, the preferred range is the same.
  • the wholly aromatic polyester of the present invention is excellent in moldability.
  • the moldability of the wholly aromatic polyester can be expressed by the fluidity at the time of melting of the wholly aromatic polyester.
  • the melt viscosity at a shear rate of 1000 sec ⁇ 1 at a temperature 10 to 40 ° C. higher than the melting point is preferably 1 ⁇ 10 5 Pa ⁇ s or less. More preferably, it is 5 Pa ⁇ s or more and 1 ⁇ 10 2 Pa ⁇ s or less.
  • melt viscosities are generally realized by having liquid crystal properties described later.
  • the melt viscosity of a polyester resin composition is considered. In the case of the polyester resin composition, the preferred range is the same.
  • the wholly aromatic polyester of the present invention may contain structural units other than the structural units represented by the above (I) to (V) as long as the effects of the present invention are not impaired. Moreover, if it is trace amount, the structural unit which does not have aromaticity may be included.
  • the wholly aromatic polyester of the present invention is polymerized using a direct polymerization method or a transesterification method.
  • a melt polymerization method a solution polymerization method, a slurry polymerization method, a solid phase polymerization method, or the like is used.
  • an acylating agent for the polymerization monomer or a monomer having an activated terminal as an acid chloride derivative can be used.
  • the acylating agent include acid anhydrides such as acetic anhydride.
  • various catalysts can be used. Typical examples include dialkyl tin oxides, diaryl tin oxides, titanium dioxide, alkoxy titanium silicates, titanium alcoholates, alkalis and alkalis of carboxylic acids. Examples include earth metal salts and Lewis acid salts such as BF 3 .
  • the amount of the catalyst used is generally about 0.001 to 1% by weight, particularly about 0.003 to 0.2% by weight, based on the total weight of the monomers.
  • liquid paraffin high heat resistant synthetic oil, inert mineral oil, or the like is used as a solvent.
  • the reaction conditions are, for example, a reaction temperature of 200 to 380 ° C. and a final ultimate pressure of 0.1 to 760 Torr (that is, 13 to 101,080 Pa).
  • the reaction temperature is 260 to 380 ° C., preferably 300 to 360 ° C.
  • the final ultimate pressure is 1 to 100 Torr (ie, 133 to 13,300 Pa), preferably 1 to 50 Torr (ie, 133 to 6,670 Pa). ).
  • all the raw material monomers, the acylating agent and the catalyst can be charged in the same reaction vessel to start the reaction (one-stage system), or the hydroxyl groups of the raw material monomers (I), (II) and (V) are acylated. After acylating with an agent, it can also be reacted with the carboxyl groups of (III) and (IV) (two-stage system).
  • the melt polymerization is performed after the inside of the reaction system reaches a predetermined temperature, and then the pressure reduction is started to a predetermined degree of pressure reduction. After the torque of the stirrer reaches a predetermined value, an inert gas is introduced, and the total aromatic polyester is discharged from the reaction system by changing from a reduced pressure state to a normal pressure to a predetermined pressure state.
  • the molecular weight of the wholly aromatic polyester produced by the above polymerization method can be further increased by solid-phase polymerization which is heated at normal pressure or reduced pressure in an inert gas.
  • Preferred conditions for the solid phase polymerization reaction are a reaction temperature of 230 to 350 ° C., preferably 260 to 330 ° C., and a final ultimate pressure of 10 to 760 Torr (ie 1,330 to 101,080 Pa).
  • the wholly aromatic polyester of the present invention exhibits optical anisotropy when melted.
  • An optical anisotropy when melted means that the wholly aromatic polyester of the present invention is a liquid crystalline polymer.
  • the fact that the wholly aromatic polyester is a liquid crystalline polymer is an indispensable element when the wholly aromatic polyester has both thermal stability and easy processability.
  • the wholly aromatic polyester composed of the structural units (I) to (V) may not form an anisotropic melt phase depending on the constituent components and the sequence distribution in the polymer. Limited to wholly aromatic polyesters that exhibit optical anisotropy when melted.
  • melt anisotropy can be confirmed by a conventional polarization inspection method using an orthogonal polarizer. More specifically, the melting anisotropy can be confirmed by melting a sample placed on a hot stage manufactured by Linkham Co., Ltd. using a polarizing microscope manufactured by Olympus and observing it at a magnification of 150 times in a nitrogen atmosphere.
  • the liquid crystalline polymer is optically anisotropic and transmits light when inserted between crossed polarizers. If the sample is optically anisotropic, for example, polarized light is transmitted even in a molten stationary liquid state.
  • the melting point (liquid crystallinity expression temperature) is preferably as high as possible from the viewpoint of heat resistance, but it is 300 to 390 ° C. in consideration of thermal degradation during polymer melt processing and the heating capability of the molding machine. Is a preferred guideline. In addition, More preferably, it is 380 degrees C or less.
  • ⁇ Polyester resin composition Various fibrous, granular, and plate-like inorganic and organic fillers can be blended in the wholly aromatic polyester of the present invention according to the purpose of use.
  • the inorganic filler to be blended in the polyester resin composition of the present invention includes fibrous, granular and plate-like ones.
  • Silica such as glass fiber, asbestos fiber, silica fiber, silica / alumina fiber, alumina fiber, zirconia fiber, boron nitride fiber, silicon nitride fiber, boron fiber, potassium titanate fiber, wollastonite as fibrous inorganic filler Fiber, magnesium sulfate fiber, aluminum borate fiber, and inorganic fibrous materials such as metal fibrous materials such as stainless steel, aluminum, titanium, copper, and brass.
  • a particularly typical fibrous filler is glass fiber.
  • the granular inorganic filler carbon black, graphite, silica, quartz powder, glass beads, milled glass fiber, glass balloon, glass powder, calcium oxalate, aluminum oxalate, kaolin, clay, diatomaceous earth, wollast Silicates such as knight, iron oxide, titanium oxide, zinc oxide, antimony trioxide, metal oxides such as alumina, metal carbonates such as calcium carbonate and magnesium carbonate, metal sulfates such as calcium sulfate and barium sulfate Examples thereof include salts, other ferrites, silicon carbide, silicon nitride, boron nitride, and various metal powders.
  • examples of the plate-like inorganic filler include mica, glass flakes, talc, and various metal foils.
  • organic fillers include heat-resistant high-strength synthetic fibers such as aromatic polyester fibers, liquid crystalline polymer fibers, aromatic polyamides, and polyimide fibers.
  • the fibrous inorganic filler is glass fiber
  • the platy filler is mica and talc.
  • the blending amount thereof is 120 parts by mass or less, preferably 20 to 80 parts by mass with respect to 100 parts by mass of the wholly aromatic polyester. It is.
  • the fiber length of glass fiber is 200 micrometers or more.
  • a sizing agent or a surface treatment agent can be used if necessary.
  • the polyester resin composition of the present invention contains the wholly aromatic polyester of the present invention, an inorganic or organic filler as an essential component, but other components are included as long as the effects of the present invention are not impaired. It may be included.
  • the other component may be any component, and examples thereof include other resins, antioxidants, stabilizers, pigments, crystal nucleating agents and the like.
  • the method for producing the polyester resin composition of the present invention is not particularly limited, and the polyester resin composition can be prepared by a conventionally known method.
  • the polyester molded article of the present invention is formed by molding the wholly aromatic polyester or polyester resin composition of the present invention.
  • the molding method is not particularly limited, and a general molding method can be employed. Examples of general molding methods include injection molding, extrusion molding, compression molding, blow molding, vacuum molding, foam molding, rotational molding, gas injection molding, and the like.
  • the polyester molded product formed by molding the wholly aromatic polyester of the present invention is excellent in heat resistance and toughness. Moreover, since the polyester molded article formed by shape
  • the wholly aromatic polyester and polyester resin composition of the present invention are excellent in moldability, a polyester molded product having a desired shape can be easily obtained.
  • polyester molded product of the present invention having the above properties include connectors, CPU sockets, relay switch parts, bobbins, actuators, noise reduction filter cases, heat fixing rolls for OA equipment, and the like.
  • Example 1 A polymerization vessel equipped with a stirrer, a reflux column, a monomer inlet, a nitrogen inlet, and a pressure reduction / outflow line was charged with the following raw material monomers, a metal catalyst, and an acylating agent, and nitrogen substitution was started.
  • melt viscosity The melt viscosity at a shear rate of 1000 sec ⁇ 1 was calculated by measuring with a capillograph manufactured by Toyo Seiki using an orifice having an inner diameter of 1 mm and a length of 20 mm at a temperature 10 to 20 ° C. higher than the melting point.
  • Softening temperature A disk with a thickness of 1 mm was formed from the prepared polyester with a hot press, and the temperature was increased at 20 ° C./min on a hot plate while applying a constant load of 12.7 MPa to the molded article. The temperature at which the needle reached 5% of the thickness of the molded product was defined as the softening temperature.
  • Example 9 is a wholly aromatic polyester of Example 6, glass fiber: ECS03T-786H manufactured by Nippon Electric Glass Co., Ltd., chopped strand having a fiber diameter of 10 ⁇ m and a length of 3 mm, and mica: Yamaguchi Mika Kogyo Co., Ltd. AB-25S manufactured and manufactured with an average particle size of 25 ⁇ m are blended and kneaded by a twin-screw extruder (TEX 30 ⁇ manufactured by Nippon Steel Works) using the formulation shown in Table 3 (content is described with respect to 100 parts by mass of wholly aromatic polyester). Thus, a pellet-shaped wholly aromatic polyester composition was obtained. After drying this wholly aromatic polyester composition at 140 ° C.
  • the evaluation injection-molded product shown in FIG. 1 has an outer diameter of 23.6 mm, 31 holes with a diameter of 3.2 mm, and a minimum wall thickness of 0.16 mm.
  • the gate is indicated by the arrow in FIG. 1 (three-point gate).
  • FIG.1 (b) represents the dimension of the injection molded product for evaluation used in the Example. Since FIG. 1 (b) is a diagram for explaining the dimensions, only one hole is shown, but actually, 31 holes are formed on a surface of ⁇ 22.2 mm. (Molding condition) Molding machine; Sumitomo Heavy Industries SE30DUZ Cylinder temperature; (Nozzle) 350 ° C.-355 ° C.-340 ° C.-330 ° C. (Example 9) Mold temperature: 140 ° C Injection speed: 50 mm / min Holding pressure: 100 MPa Holding time: 2 sec Cooling time: 10 sec Screw rotation speed: 120rpm Screw back pressure: 1.2 MPa
  • Example 10 uses the wholly aromatic polyester of Example 5, glass fibers and mica in the same manner as in Example 9, and uses a twin screw extruder (TEX 30 ⁇ manufactured by Nippon Steel Works). ) To obtain a pellet-shaped wholly aromatic polyester composition. After drying this wholly aromatic polyester composition at 140 ° C. for 3 hours, the molded product was injection-molded using an injection molding machine in the same manner as in Example 9. As a result, the moldability was good and cracks in the molded product did not occur. Showed good toughness characteristics. The results are shown in Table 3. In the molding conditions, only the cylinder temperature was changed to 360 ° C.-365 ° C.-350 ° C.-340 ° C.
  • Comparative Example 9 uses the wholly aromatic polyester of Comparative Example 6 and uses glass fibers and mica in the same manner as in Example 9 in the formulation shown in Table 3 and is a twin-screw extruder (TEX 30 ⁇ manufactured by Nippon Steel Works). After mixing and kneading to obtain a pellet-shaped wholly aromatic polyester composition, the molded product was injection-molded in the same manner as in Example 9 to evaluate toughness (cracking of the molded product). These results are shown in Table 3. Of the molding conditions, only the cylinder temperature condition was changed to 390 ° C-395 ° C-380 ° C-370 ° C.
  • Comparative Example 10 uses the wholly aromatic polyester of Comparative Example 8 and uses glass fibers and mica in the same manner as in Example 9 in the formulation shown in Table 3 and is a twin screw extruder (TEX 30 ⁇ manufactured by Nippon Steel Works). After mixing and kneading to obtain a pellet-shaped wholly aromatic polyester composition, the molded product was injection-molded in the same manner as in Example 9 to evaluate toughness (cracking of the molded product). These results are shown in Table 3. In the molding conditions, only the cylinder temperature was changed to 380 ° C.-385 ° C.-370 ° C.-360 ° C.
  • Example 9 to 10 and Comparative Examples 9 to 10 the melting point, the crystallization temperature, the heat of crystallization, the melt viscosity, and the softening temperature were evaluated in the same manner as in Example 1 and the like. The evaluation results are shown in Table 3.

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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)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne un polyester entièrement aromatique qui a une excellente résistance à la chaleur et une excellente ténacité. Ce polyester entièrement aromatique est composé d'unités constitutives représentées par les formules générales (I), (II), (III), (IV) et (V). Par rapport aux unités constitutives totales, l'unité constitutive de formule (I) est contenue dans une quantité de 40-70 % en moles, l'unité constitutive de formule (II) est contenue dans une quantité de 7-14 % en moles, l'unité constitutive de formule (III) est contenue dans une quantité de 8-26,5 % en moles, l'unité constitutive de formule (IV) est contenue dans une quantité de 0-10 % en moles et l'unité constitutive de formule (V) est contenue dans une quantité de 8-26,5 % en moles, la teneur totale de l'unité constitutive de formule (II) et de l'unité constitutive de formule (IV) étant de 12-17 % en moles.
PCT/JP2012/070927 2011-10-05 2012-08-17 Polyester entièrement aromatique, composition de résine de polyester et article moulé en polyester Ceased WO2013051346A1 (fr)

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JP2013537452A JP6189750B2 (ja) 2011-10-05 2012-08-17 全芳香族ポリエステル、ポリエステル樹脂組成物、及びポリエステル成形品

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JP2011-221091 2011-10-05
JP2011221091 2011-10-05

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TW (1) TW201333066A (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023199854A1 (fr) 2022-04-11 2023-10-19 東レ株式会社 Résine de polyester à cristaux liquides, composition de résine de polyester à cristaux liquides et produit moulé la comprenant

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5962630A (ja) * 1982-07-26 1984-04-10 セラニ−ズ・コ−ポレイシヨン 比較的低濃度の６−オキシ−２−ナフトイル部分を含む異方性溶融加工可能なポリエステル
JPS62231018A (ja) * 1986-03-27 1987-10-09 Sumitomo Chem Co Ltd ポリエステル繊維
JPH01261417A (ja) * 1988-04-13 1989-10-18 Polyplastics Co 溶融時に光学的異方性を示すポリエステル樹脂及び樹脂組成物
JP2005501150A (ja) * 2001-08-21 2005-01-13 ティコナ・エルエルシー 高度の延伸適性をもつ異方性メルト形成性ポリマー
JP2009221406A (ja) * 2008-03-18 2009-10-01 Ueno Fine Chem Ind Ltd 液晶ポリエステルの製造方法
JP2010174114A (ja) * 2009-01-29 2010-08-12 Toray Ind Inc 液晶性樹脂組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5962630A (ja) * 1982-07-26 1984-04-10 セラニ−ズ・コ−ポレイシヨン 比較的低濃度の６−オキシ−２−ナフトイル部分を含む異方性溶融加工可能なポリエステル
JPS62231018A (ja) * 1986-03-27 1987-10-09 Sumitomo Chem Co Ltd ポリエステル繊維
JPH01261417A (ja) * 1988-04-13 1989-10-18 Polyplastics Co 溶融時に光学的異方性を示すポリエステル樹脂及び樹脂組成物
JP2005501150A (ja) * 2001-08-21 2005-01-13 ティコナ・エルエルシー 高度の延伸適性をもつ異方性メルト形成性ポリマー
JP2009221406A (ja) * 2008-03-18 2009-10-01 Ueno Fine Chem Ind Ltd 液晶ポリエステルの製造方法
JP2010174114A (ja) * 2009-01-29 2010-08-12 Toray Ind Inc 液晶性樹脂組成物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023199854A1 (fr) 2022-04-11 2023-10-19 東レ株式会社 Résine de polyester à cristaux liquides, composition de résine de polyester à cristaux liquides et produit moulé la comprenant
KR20250005963A (ko) 2022-04-11 2025-01-10 도레이 카부시키가이샤 액정 폴리에스테르 수지, 액정 폴리에스테르 수지 조성물 및 그로부터 이루어지는 성형품

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JP6189750B2 (ja) 2017-08-30
JPWO2013051346A1 (ja) 2015-03-30
TW201333066A (zh) 2013-08-16

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