WO2017068869A1 - Polyester amide entièrement aromatique, et son procédé de production - Google Patents

Polyester amide entièrement aromatique, et son procédé de production Download PDF

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Publication number
WO2017068869A1
WO2017068869A1 PCT/JP2016/075452 JP2016075452W WO2017068869A1 WO 2017068869 A1 WO2017068869 A1 WO 2017068869A1 JP 2016075452 W JP2016075452 W JP 2016075452W WO 2017068869 A1 WO2017068869 A1 WO 2017068869A1
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WO
WIPO (PCT)
Prior art keywords
mol
aromatic polyester
acid
polyester amide
wholly aromatic
Prior art date
Application number
PCT/JP2016/075452
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English (en)
Japanese (ja)
Inventor
俊紀 川原
俊明 横田
Original Assignee
ポリプラスチックス株式会社
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Application filed by ポリプラスチックス株式会社 filed Critical ポリプラスチックス株式会社
Priority to CN201680054977.9A priority Critical patent/CN108026269A/zh
Priority to JP2017507028A priority patent/JP6157779B1/ja
Publication of WO2017068869A1 publication Critical patent/WO2017068869A1/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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides

Definitions

  • the present invention relates to a wholly aromatic polyester amide and a method for producing the same.
  • liquid crystalline polymers have excellent fluidity, mechanical strength, heat resistance, chemical resistance, electrical properties and the like in a well-balanced manner, they are widely used as high-performance engineering plastics.
  • a wholly aromatic polyester amide is used together with a wholly aromatic polyester.
  • Patent Document 1 discloses an aromatic polyester amide obtained by reacting p-aminophenol, 4-hydroxybenzoic acid, 4,4'-dihydroxybiphenyl, and terephthalic acid.
  • wholly aromatic polyester amides do not have sufficient heat resistance and are required to have improved heat resistance. Further, the wholly aromatic polyester amide is also required to be excellent in ease of production, that is, excellent in manufacturability, based on the excellent polymerizability of the monomer.
  • an object of the present invention is to provide a wholly aromatic polyester amide having excellent balance between heat resistance and manufacturability.
  • the inventors of the present invention have made extensive studies to solve the above problems. As a result, it has been found that the above-mentioned problems can be solved by a wholly aromatic polyester amide composed of specific structural units, and the content of each structural unit is in a specific range, and the present invention has been completed. More specifically, the present invention provides the following.
  • Consists of the following structural units (I) to (V) as essential constituents The content of the structural unit (I) is 50 to 69 mol% with respect to all the structural units, The content of the structural unit (II) is 9.2 to 22.5 mol% with respect to all the structural units, The content of the structural unit (III) is 2.5 to 6.3 mol% with respect to all the structural units, The content of the structural unit (IV) is 8.5 to 24 mol% with respect to all the structural units, A wholly aromatic polyester amide having an optical anisotropy when melted, wherein the content of the structural unit (V) is from 1 to 7 mol% based on the total structural units.
  • the wholly aromatic polyester amide according to claim 1 or 2 wherein the difference between the melting point and the deflection temperature under load is 110 ° C or less,
  • the deflection temperature under load was obtained by melt-kneading 60% by mass of the wholly aromatic polyester amide and 40% by mass of milled fiber having an average fiber diameter of 11 ⁇ m and an average fiber length of 75 ⁇ m at the melting point of the wholly aromatic polyester amide + 20 ° C.
  • a wholly aromatic polyester amide measured in the state of the polyester resin composition obtained in this manner.
  • 1,4-phenylenedicarboxylic acid is obtained by acylating 4-hydroxybenzoic acid, 4,4′-dihydroxybiphenyl, and N-acetyl-p-aminophenol with a fatty acid anhydride in the presence of a fatty acid metal salt.
  • the amount of 4-hydroxybenzoic acid used is 50 to 69 mol%
  • the amount of 1,4-phenylenedicarboxylic acid used is 9.2 to 22.5 mol%
  • the amount of 1,3-phenylenedicarboxylic acid used is 2.5 to 6.3 mol%
  • the amount of 4,4′-dihydroxybiphenyl used is 8.5 to 24 mol%
  • the amount of N-acetyl-p-aminophenol used is 1-7 mol%
  • the method wherein the amount of the fatty acid anhydride used is 1.02 to 1.04 times the total hydroxyl equivalent of 4-hydroxybenzoic acid, 4,4′-dihydroxybiphenyl,
  • the total number of moles of 1,4-phenylene dicarboxylic acid and 1,3-phenylene dicarboxylic acid is 1 to the total number of moles of 4,4′-dihydroxybiphenyl and N-acetyl-p-aminophenol. 1.06 times, or the total number of moles of 4,4′-dihydroxybiphenyl and N-acetyl-p-aminophenol is the sum of 1,4-phenylene dicarboxylic acid and 1,3-phenylene dicarboxylic acid
  • the wholly aromatic polyester amide of the present invention which consists of a specific structural unit and exhibits optical anisotropy when melted, is excellent in balance between heat resistance and manufacturability.
  • the wholly aromatic polyester amide of the present invention is not so high in molding processing temperature that it can be injection-molded, extruded, compression-molded, etc. without using a molding machine having a special structure.
  • the wholly aromatic polyester amide of the present invention is excellent in moldability and can be molded using various molding machines. As a result, it can be easily processed into various three-dimensional molded products, fibers, films and the like. For this reason, molded products 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 amide of the present invention, can be easily obtained. It is done.
  • the wholly aromatic polyester amide of the present invention comprises the following structural unit (I), the following structural unit (II), the following structural unit (III), the following structural unit (IV), and the following structural unit (V).
  • the structural unit (I) is derived from 4-hydroxybenzoic acid (hereinafter also referred to as “HBA”).
  • HBA 4-hydroxybenzoic acid
  • the wholly aromatic polyester amide of the present invention contains 50 to 69 mol% of the structural unit (I) with respect to all the structural units. When the content of the structural unit (I) is less than 50 mol% or exceeds 69 mol%, at least one of heat resistance and manufacturability tends to be insufficient.
  • the structural unit (II) is derived from 1,4-phenylenedicarboxylic acid (hereinafter also referred to as “TA”).
  • the wholly aromatic polyester amide of the present invention contains 9.2 to 22.5 mol% of the structural unit (II) with respect to all the structural units. When the content of the structural unit (II) is less than 9.2 mol% or exceeds 22.5 mol%, at least one of heat resistance and manufacturability tends to be insufficient.
  • the structural unit (III) is derived from 1,3-phenylenedicarboxylic acid (hereinafter also referred to as “IA”).
  • the wholly aromatic polyester amide of the present invention contains 2.5 to 6.3 mol% of the structural unit (III) with respect to all the structural units. When the content of the structural unit (III) is less than 2.5 mol% or exceeds 6.3 mol%, at least one of heat resistance and manufacturability tends to be insufficient.
  • the structural unit (IV) is derived from 4,4′-dihydroxybiphenyl (hereinafter also referred to as “BP”).
  • BP 4,4′-dihydroxybiphenyl
  • the wholly aromatic polyester amide of the present invention contains 8.5 to 24 mol% of the structural unit (IV) with respect to all the structural units. If the content of the structural unit (IV) is less than 8.5 mol% or exceeds 24 mol%, at least one of heat resistance and manufacturability tends to be insufficient.
  • the structural unit (V) is derived from N-acetyl-p-aminophenol (hereinafter also referred to as “APAP”).
  • the wholly aromatic polyester amide of the present invention contains 1 to 7 mol% of the structural unit (V) based on the total structural units.
  • the content of the structural unit (V) is less than 1 mol%, the heat resistance is good, but the manufacturability tends to be insufficient. If the content of the structural unit (V) exceeds 7 mol%, at least one of heat resistance and manufacturability tends to be insufficient.
  • the wholly aromatic polyester amide 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, so that heat resistance and manufacturability are improved. Excellent balance.
  • DTUL a difference between a melting point and a deflection temperature under load
  • this difference is 110 ° C. or less, the heat resistance tends to increase, which is preferable.
  • DTUL is obtained by melt-kneading 60% by mass of the wholly aromatic polyester amide and 40% by mass of milled fiber having an average fiber diameter of 11 ⁇ m and an average fiber length of 75 ⁇ m at the melting point of the wholly aromatic polyester amide + 20 ° C. It is a value measured in the state of the polyester resin composition, and can be measured in accordance with ISO75-1,2.
  • the wholly aromatic polyester amide 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 fatty acid anhydrides such as acetic anhydride.
  • various catalysts can be used. Typical examples include dialkyl tin oxide, diaryl tin oxide, titanium dioxide, alkoxy titanium silicates, titanium alcoholates, fatty acid metal salts, BF 3 Lewis acid salts such as are mentioned, and fatty acid metal salts are preferred.
  • 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). Particularly in a melt reaction, for example, a reaction temperature of 260 to 380 ° C., preferably 300 to 360 ° C., a final ultimate pressure of 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 HBA, TA, IA, BP, and APAP
  • the acylating agent can be charged into the same reaction vessel to start the reaction (one-stage system)
  • the APAP hydroxyl group can be acylated with an acylating agent and then reacted with the carboxyl groups of TA and IA (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 amide is discharged from the reaction system through a normal pressure from a reduced pressure state to a predetermined pressure state.
  • the wholly aromatic polyester amide produced by the above polymerization method can further increase the molecular weight by solid-phase polymerization that is heated in an inert gas at normal pressure or reduced pressure.
  • 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 method for producing a wholly aromatic polyester amide of the present invention comprises acylating 4-hydroxybenzoic acid, 4,4′-dihydroxybiphenyl, and N-acetyl-p-aminophenol with a fatty acid anhydride in the presence of a fatty acid metal salt.
  • the amount of 4-hydroxybenzoic acid used is 50 to 69 mol%
  • the amount of 1,4-phenylenedicarboxylic acid used is 9.2 to 22.5 mol%
  • the amount of 1,3-phenylenedicarboxylic acid used is 2.5 to 6.3 mol%
  • the amount of 4,4′-dihydroxybiphenyl used is 8.5 to 24 mol%
  • the amount of N-acetyl-p-aminophenol used is 1-7 mol% It is preferable that The amount of the fatty acid anhydride used is 1.02 to 1.04 times the total hydroxyl equivalent of
  • the fatty acid metal salt is an acetic acid metal salt and the fatty acid anhydride is acetic anhydride.
  • the total number of moles of 1,4-phenylene dicarboxylic acid and 1,3-phenylene dicarboxylic acid is 1 to the total number of moles of 4,4′-dihydroxybiphenyl and N-acetyl-p-aminophenol. 1.06 times or the total number of moles of 4,4′-dihydroxybiphenyl and N-acetyl-p-aminophenol is 1,4-phenylenedicarboxylic acid and 1,3-phenylenedicarboxylic acid It is more preferably 1 to 1.06 times the total number of moles.
  • the wholly aromatic polyester amide of the present invention exhibits optical anisotropy when melted.
  • An optical anisotropy when melted means that the wholly aromatic polyester amide of the present invention is a liquid crystalline polymer.
  • the fact that the wholly aromatic polyester amide is a liquid crystalline polymer is an essential element for the wholly aromatic polyester amide to have both heat stability and easy processability.
  • the wholly aromatic polyester amides 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. Is limited to wholly aromatic polyester amides exhibiting 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 in consideration of thermal degradation during polymer melt processing, heating capability of the molding machine, etc., it is more than 340 ° C. and not more than 370 ° C. It is a preferable standard. More preferably, it is 345 to 365 ° C.
  • ⁇ Polyesteramide resin composition Various fibrous, granular, and plate-like inorganic and organic fillers can be blended with the wholly aromatic polyester amide of the present invention according to the purpose of use.
  • the inorganic filler to be blended in the polyesteramide resin composition of the present invention there are 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
  • Inorganic fibrous materials such as fibers, magnesium sulfate fibers, aluminum borate fibers, and 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 amide. Part.
  • a sizing agent or a surface treatment agent can be used if necessary.
  • the polyesteramide resin composition of the present invention contains the wholly aromatic polyesteramide of the present invention and an inorganic or organic filler as essential components. Ingredients 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 production method of the polyesteramide resin composition of the present invention is not particularly limited, and the polyesteramide resin composition can be prepared by a conventionally known method.
  • the polyesteramide molded article of the present invention is formed by molding the wholly aromatic polyesteramide or the polyesteramide 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.
  • a polyesteramide molded product obtained by molding the wholly aromatic polyesteramide of the present invention is excellent in heat resistance and toughness. Moreover, since the polyesteramide molded article formed by molding the polyesteramide resin composition of the present invention is excellent in heat resistance and toughness and contains an inorganic or organic filler, mechanical strength and the like are further improved.
  • the wholly aromatic polyester amide and the polyester amide resin composition of the present invention are excellent in moldability, a polyester amide molded product having a desired shape can be easily obtained.
  • polyesteramide 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 decompression / outflow line was charged with the following raw material monomers, fatty acid metal salt catalyst, and acylating agent, and nitrogen substitution was started.
  • Manufacturability The behavior when the polymer was discharged from the lower part of the polymerization vessel was observed, and the manufacturability was evaluated according to the following criteria. The results are shown in Tables 1 to 4. ⁇ : The polymer was discharged as a strand without any problem, and when this strand could be cut into a pellet, it was evaluated that the manufacturability was good. X: Manufacturability was evaluated to be poor when solidification or the like was caused in the container during polymerization and the polymer could not be discharged, or when the polymer could be discharged as a strand but the strand could not be cut.
  • Examples 2 to 16 Comparative Examples 1 to 8> A polymer was obtained in the same manner as in Example 1 except that the types of raw material monomers and the charging ratio (mol%) were as shown in Tables 1 to 3. Moreover, the same evaluation as Example 1 was performed. The evaluation results are shown in Tables 1 to 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)
  • Polyamides (AREA)

Abstract

L'invention concerne un polyester amide entièrement aromatique présentant un excellent équilibre entre la résistance à la chaleur et la productibilité. Le polyester amide entièrement aromatique selon l'invention contient, à titre de composants constitutifs essentiels, des motifs constitutifs (I) à (V), et contient, par rapport à tous les motifs constitutifs, de 50 à 69 % en mol de motif constitutif (I), de 9,2 à 22,5 % en mol de motif constitutif (II), de 2,5 à 6,3 % en mol de motif constitutif (III), de 8,5 à 24 % en mol de motif constitutif (IV), et de 1 à 7 % en mol de motif constitutif (V). A l'état fondu, le polyester amide entièrement aromatique présente une anisotropie optique.
PCT/JP2016/075452 2015-10-21 2016-08-31 Polyester amide entièrement aromatique, et son procédé de production WO2017068869A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201680054977.9A CN108026269A (zh) 2015-10-21 2016-08-31 全芳香族聚酯酰胺和其制造方法
JP2017507028A JP6157779B1 (ja) 2015-10-21 2016-08-31 全芳香族ポリエステルアミド及びその製造方法

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JP2015-207436 2015-10-21
JP2015207436 2015-10-21

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CN (1) CN108026269A (fr)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018066416A1 (fr) * 2016-10-07 2018-04-12 ポリプラスチックス株式会社 Composition de résine composite, et composant électronique fabriqué à partir de ladite composition de résine composite
WO2018066417A1 (fr) * 2016-10-07 2018-04-12 ポリプラスチックス株式会社 Composition de résine composite, et raccord fabriqué à partir de ladite composition de résine composite
WO2018074155A1 (fr) * 2016-10-21 2018-04-26 ポリプラスチックス株式会社 Composition de résine composite et composant électronique fabriqué à partir de ladite composition de résine composite
WO2018074156A1 (fr) * 2016-10-21 2018-04-26 ポリプラスチックス株式会社 Composition de résine composite et connecteur moulé formé à partir de cette dernière
WO2018116889A1 (fr) * 2016-12-22 2018-06-28 ポリプラスチックス株式会社 Composition de résine cristalline liquide pour relais montés en surface et relais monté en surface l'utilisant
WO2018116888A1 (fr) * 2016-12-21 2018-06-28 ポリプラスチックス株式会社 Composition de résine cristalline liquide pour relais montés en surface et relais monté en surface utilisant celle-ci

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112250846B (zh) 2020-10-30 2022-12-02 金发科技股份有限公司 一种液晶聚酯、液晶聚酯组合物及应用

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JPH06263857A (ja) * 1993-03-17 1994-09-20 Dainippon Ink & Chem Inc 共重合ポリエステル類およびその製造法
WO1998056578A1 (fr) * 1997-06-13 1998-12-17 Nippon Petrochemicals Company, Limited Composite lie et composition adhesive pour ledit composite
WO2013115168A1 (fr) * 2012-01-31 2013-08-08 Ｊｘ日鉱日石エネルギー株式会社 Amide de polyester à cristaux liquides, composition de résine d'amide de polyester à cristaux liquides, et article moulé

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JPH01319534A (ja) * 1988-06-21 1989-12-25 Mitsubishi Kasei Corp 芳香族ポリエステルアミド及びその製造方法
ES2010297A6 (es) * 1988-07-27 1989-11-01 Cables Comunicaciones Un procedimiento para la preparacion de nuevas copoliesteramidas termotropas aromaticas.

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Publication number Priority date Publication date Assignee Title
JPH06263857A (ja) * 1993-03-17 1994-09-20 Dainippon Ink & Chem Inc 共重合ポリエステル類およびその製造法
WO1998056578A1 (fr) * 1997-06-13 1998-12-17 Nippon Petrochemicals Company, Limited Composite lie et composition adhesive pour ledit composite
WO2013115168A1 (fr) * 2012-01-31 2013-08-08 Ｊｘ日鉱日石エネルギー株式会社 Amide de polyester à cristaux liquides, composition de résine d'amide de polyester à cristaux liquides, et article moulé

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018066416A1 (fr) * 2016-10-07 2018-04-12 ポリプラスチックス株式会社 Composition de résine composite, et composant électronique fabriqué à partir de ladite composition de résine composite
WO2018066417A1 (fr) * 2016-10-07 2018-04-12 ポリプラスチックス株式会社 Composition de résine composite, et raccord fabriqué à partir de ladite composition de résine composite
WO2018074155A1 (fr) * 2016-10-21 2018-04-26 ポリプラスチックス株式会社 Composition de résine composite et composant électronique fabriqué à partir de ladite composition de résine composite
WO2018074156A1 (fr) * 2016-10-21 2018-04-26 ポリプラスチックス株式会社 Composition de résine composite et connecteur moulé formé à partir de cette dernière
WO2018116888A1 (fr) * 2016-12-21 2018-06-28 ポリプラスチックス株式会社 Composition de résine cristalline liquide pour relais montés en surface et relais monté en surface utilisant celle-ci
WO2018116889A1 (fr) * 2016-12-22 2018-06-28 ポリプラスチックス株式会社 Composition de résine cristalline liquide pour relais montés en surface et relais monté en surface l'utilisant

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TW201723022A (zh) 2017-07-01
JP6157779B1 (ja) 2017-07-05
CN108026269A (zh) 2018-05-11
TWI692491B (zh) 2020-05-01
JPWO2017068869A1 (ja) 2017-10-19

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