WO2018139393A1 - Wholly aromatic polyester and polyester resin composition - Google Patents
Wholly aromatic polyester and polyester resin composition Download PDFInfo
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- WO2018139393A1 WO2018139393A1 PCT/JP2018/001718 JP2018001718W WO2018139393A1 WO 2018139393 A1 WO2018139393 A1 WO 2018139393A1 JP 2018001718 W JP2018001718 W JP 2018001718W WO 2018139393 A1 WO2018139393 A1 WO 2018139393A1
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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
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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
- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/42—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes polyesters; polyethers; polyacetals
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/42—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes polyesters; polyethers; polyacetals
- H01B3/421—Polyesters
Abstract
Description
全構成単位に対して構成単位(I)の含有量は60~85モル%であり、
全構成単位に対して構成単位(II)の含有量は12~40モル%であり、
全構成単位に対して構成単位(III)または(IV)の含有量は0.1~3モル%であり、
全構成単位に対して構成単位(I)、(II)、及び(III)または(IV)の合計の含有量は100モル%である、
全芳香族ポリエステル。
The content of the structural unit (I) is 60 to 85 mol% with respect to all the structural units,
The content of the structural unit (II) is 12 to 40 mol% with respect to all the structural units,
The content of the structural unit (III) or (IV) is 0.1 to 3 mol% with respect to all the structural units,
The total content of the structural units (I), (II), and (III) or (IV) is 100 mol% with respect to all the structural units.
Totally aromatic polyester.
本発明に係る全芳香族ポリエステルは、必須の構成成分として、下記構成単位(I)、(II)、及び(III)または(IV)からなり、全構成単位に対して構成単位(I)の含有量は60~85モル%であり、全構成単位に対して構成単位(II)の含有量は12~40モル%であり、全構成単位に対して構成単位(III)または(IV)の含有量は0.1~3モル%であり、全構成単位に対して構成単位(I)、(II)、及び(III)または(IV)の合計の含有量は100モル%である。
The wholly aromatic polyester according to the present invention comprises the following constituent units (I), (II), and (III) or (IV) as essential constituent components, and the constituent units (I) The content is 60 to 85 mol%, the content of the structural unit (II) is 12 to 40 mol% with respect to all the structural units, and the structural unit (III) or (IV) is based on the total structural units. The content is 0.1 to 3 mol%, and the total content of the structural units (I), (II), and (III) or (IV) is 100 mol% with respect to all the structural units.
なお、結晶化熱量とは示差熱量測定において、ポリマーを室温から20℃/分の昇温条件で測定した際に観測される吸熱ピーク温度(Tm1)の観測後、(Tm1+40)℃の温度で2分間保持した後、20℃/分の降温条件で測定した際に観測される発熱ピーク温度のピークより求められる発熱ピークの熱量を指す。 The total crystallization heat amount of the wholly aromatic polyester of the present invention is preferably 2.5 J / g or more, more preferably 2.5 to 4.4 J / g. If the crystallization heat amount, which indicates the crystallization state of the polymer determined by differential calorimetry, is less than 2.5 J / g, the crystallinity is lowered and the hydrolysis resistance is deteriorated. Moreover, when the amount of crystallization heat exceeds 4.4 J / g, toughness will become low and it is not preferable.
It should be noted that the heat of crystallization is 2 at a temperature of (Tm1 + 40) ° C. after observing the endothermic peak temperature (Tm1) observed when the polymer is measured at room temperature from 20 ° C./min. It refers to the calorific value of the exothermic peak obtained from the peak of the exothermic peak temperature that is observed when the temperature is measured for 20 ° C./min.
上記の本発明の全芳香族ポリエステルには、使用目的に応じて各種の繊維状、粉粒状、板状の無機及び有機の充填剤を配合することができる。 [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.
本発明のポリエステル成形品は、本発明の全芳香族ポリエステル又はポリエステル樹脂組成物を成形してなる。成形方法としては、特に限定されず一般的な成形方法を採用することができる。一般的な成形方法としては、射出成形、押出成形、圧縮成形、ブロー成形、真空成形、発泡成形、回転成形、ガスインジェクション成形、インフレーション成形等の方法を例示することができる。 [Polyester molded product]
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, inflation molding, and the like.
撹拌機、還流カラム、モノマー投入口、窒素導入口、減圧/流出ラインを備えた重合容器に、以下の原料モノマー、脂肪酸金属塩触媒、アシル化剤を仕込み、窒素置換を開始した。
(I)6-ヒドロキシ-2-ナフトエ酸1.44モル(76モル%)(HNA)
(II)4-ヒドロキシ安息香酸0.44モル(23.3モル%)(HBA)
(III)テレフタル酸0.1モル(0.7モル%)(TA)
酢酸カリウム触媒22.5mg
無水酢酸196g(HNAとHBAの合計の水酸基当量の1.02倍)
原料を仕込んだ後、反応系の温度を140℃に上げ、140℃で2時間反応させた。その後、更に340℃まで4.1時間かけて昇温し、そこから15分かけて10Torr(即ち1330Pa)まで減圧にして、酢酸、過剰の無水酢酸、その他の低沸分を留出させながら重縮合を行った。撹拌トルクが所定の値に達した後、窒素を導入して減圧状態から常圧を経て加圧状態にして、重合容器の下部からポリマーを排出した。 <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.
(I) 1.44 mol (76 mol%) of 6-hydroxy-2-naphthoic acid (HNA)
(II) 4-hydroxybenzoic acid 0.44 mol (23.3 mol%) (HBA)
(III) Terephthalic acid 0.1 mol (0.7 mol%) (TA)
Potassium acetate catalyst 22.5mg
196 g of acetic anhydride (1.02 times the total hydroxyl equivalent of HNA and HBA)
After the raw materials were charged, the temperature of the reaction system was raised to 140 ° C. and reacted at 140 ° C. for 2 hours. Thereafter, the temperature is further increased to 340 ° C. over 4.1 hours, and then reduced to 10 Torr (ie, 1330 Pa) over 15 minutes, and acetic acid, excess acetic anhydride, and other low-boiling components are distilled off. Condensation was performed. After the stirring torque reached a predetermined value, nitrogen was introduced and the pressure was changed from a reduced pressure state to a normal pressure, and the polymer was discharged from the lower part of the polymerization vessel.
実施例1の全芳香族ポリエステルについて、融点、結晶化温度、結晶化熱量、溶融粘度、熱安定性、及び耐加水分解性の評価を以下の方法で行った。評価結果を表1に示す。 <Evaluation>
About the wholly aromatic polyester of Example 1, evaluation of melting | fusing point, crystallization temperature, crystallization calorie | heat amount, melt viscosity, thermal stability, and hydrolysis resistance was performed with the following method. The evaluation results are shown in Table 1.
示差走査熱量計(DSC、パーキンエルマー社製)にて、全芳香族ポリエステルを室温から20℃/分の昇温条件で測定した際に観測される吸熱ピーク温度(Tm1)の観測後、(Tm1+40)℃の温度で2分間保持した後、20℃/分の降温条件で室温まで一旦冷却した後、再度、20℃/分の昇温条件で測定した際に観測される吸熱ピークの温度を測定した。 [Melting point]
After observation of the endothermic peak temperature (Tm1) observed when the wholly aromatic polyester was measured under a temperature rising condition from room temperature to 20 ° C./min with a differential scanning calorimeter (DSC, manufactured by Perkin Elmer), (Tm1 + 40) ) After holding at a temperature of 2 ° C. for 2 minutes, after cooling to room temperature under a temperature drop condition of 20 ° C./minute, measure the temperature of the endothermic peak observed when measuring again under a temperature increase condition of 20 ° C./minute. did.
示差走査熱量計(DSC、パーキンエルマー社製)にて、全芳香族ポリエステルを室温から20℃/分の昇温条件で測定した際に観測される吸熱ピーク温度(Tm1)の観測後、(Tm1+40)℃の温度で2分間保持した後、20℃/分の降温条件で測定した際に観測される発熱ピーク温度を測定した。 [Crystallizing temperature]
After observation of the endothermic peak temperature (Tm1) observed when the wholly aromatic polyester was measured under a temperature rising condition from room temperature to 20 ° C./min with a differential scanning calorimeter (DSC, manufactured by Perkin Elmer), (Tm1 + 40) ) After holding at a temperature of 2 ° C. for 2 minutes, an exothermic peak temperature observed when measured under a temperature drop condition of 20 ° C./min was measured.
示差走査熱量計(DSC、パーキンエルマー社製)にて、全芳香族ポリエステルを室温から20℃/分の昇温条件で測定した際に観測される吸熱ピーク温度(Tm1)の観測後、(Tm1+40)℃の温度で2分間保持した後、20℃/分の降温条件で測定した際に観測される発熱ピーク温度のピークより求められる発熱ピークの熱量を測定した。 [Amount of crystallization]
After observation of the endothermic peak temperature (Tm1) observed when the wholly aromatic polyester was measured under a temperature rising condition from room temperature to 20 ° C./min with a differential scanning calorimeter (DSC, manufactured by Perkin Elmer), (Tm1 + 40) ) After holding at a temperature of 2 ° C. for 2 minutes, the calorific value of the exothermic peak obtained from the peak of the exothermic peak temperature observed when the temperature was measured under a temperature decreasing condition of 20 ° C./min was measured.
(株)東洋精機製作所製キャピログラフを使用し、全芳香族ポリエステルの融点よりも10~30℃高い温度で、内径0.5mm、長さ30mmのオリフィスを用いて、剪断速度1000/秒で、ISO11443に準拠して、全芳香族ポリエステルの溶融粘度を測定した。 [Melt viscosity]
ISO 11443 using a capilograph manufactured by Toyo Seiki Seisakusho Co., Ltd., using an orifice having an inner diameter of 0.5 mm and a length of 30 mm at a temperature 10 to 30 ° C. higher than the melting point of the wholly aromatic polyester and a shear rate of 1000 / sec. The melt viscosity of the wholly aromatic polyester was measured.
示差熱熱重量同時測定装置(TG/DTA、セイコーインスツル(株)製)を使用し、全芳香族ポリエステル10mgを窒素気流下にて、370℃で、30分保持した際の重量減少を発生ガス量として測定した。なお、発生ガス量が15000ppm未満であれば良好と判断した。 [Thermal stability]
Using a differential thermal thermogravimetric simultaneous measurement device (TG / DTA, manufactured by Seiko Instruments Inc.), 10mg of total aromatic polyester is reduced in weight when held at 370 ° C for 30 minutes under a nitrogen stream. Measured as gas amount. In addition, it was judged that it was favorable if the amount of generated gas was less than 15000 ppm.
全芳香族ポリエステルについて121℃、湿度100%、2気圧条件下でプレッシャークッカーテストを100時間行い、その全芳香族ポリエステルについて溶融粘度の測定を行い、初期値に対する保持率を求めた。なお、初期値に対する保持率が90%以上であれば良好と判断した。 [Hydrolysis resistance]
The fully aromatic polyester was subjected to a pressure cooker test for 100 hours under the conditions of 121 ° C., 100% humidity and 2 atm. The melt viscosity of the wholly aromatic polyester was measured to determine the retention rate relative to the initial value. In addition, it was judged that the retention rate relative to the initial value was 90% or more.
原料モノマーの種類、仕込み比率(モル%)を表1に示す通りとした以外は、実施例1と同様にしてポリマーを得た。得られたポリマーを、窒素雰囲気下で室温から290℃まで20分かけて昇温し、3時間保持した後、放冷し、更なるポリマーを得た。また、実施例1と同様の評価を行った。評価結果を表1に示す。 <Example 2>
A polymer was obtained in the same manner as in Example 1 except that the type of raw material monomer and the charging ratio (mol%) were as shown in Table 1. The obtained polymer was heated from room temperature to 290 ° C. over 20 minutes in a nitrogen atmosphere, held for 3 hours, and then allowed to cool to obtain a further polymer. Moreover, the same evaluation as Example 1 was performed. The evaluation results are shown in Table 1.
撹拌機、還流カラム、モノマー投入口、窒素導入口、減圧/流出ラインを備えた重合容器に、以下の原料モノマー、脂肪酸金属塩触媒、アシル化剤を仕込み、窒素置換を開始した。
(I)6-ヒドロキシ-2-ナフトエ酸1.51モル(81モル%)(HNA)
(II)4-ヒドロキシ安息香酸0.34モル(18モル%)(HBA)
(IV)4,4’-ジヒドロキシビフェニル0.02モル(1モル%)(BP)
酢酸カリウム触媒22.5mg
無水酢酸196g(HNAとHBAとBPの合計の水酸基当量の1.02倍)
原料を仕込んだ後、反応系の温度を140℃に上げ、140℃で2時間反応させた。その後、更に370℃まで4.7時間かけて昇温し、そこから15分かけて10Torr(即ち1330Pa)まで減圧にして、酢酸、過剰の無水酢酸、その他の低沸分を留出させながら重縮合を行った。撹拌トルクが所定の値に達した後、窒素を導入して減圧状態から常圧を経て加圧状態にして、重合容器の下部からポリマーを排出した。また、実施例1と同様の評価を行った。評価結果を表1に示す。 <Example 3>
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.
(I) 6-hydroxy-2-naphthoic acid 1.51 mol (81 mol%) (HNA)
(II) 4-hydroxybenzoic acid 0.34 mol (18 mol%) (HBA)
(IV) 0.02 mol (1 mol%) of 4,4′-dihydroxybiphenyl (BP)
Potassium acetate catalyst 22.5mg
196 g of acetic anhydride (1.02 times the total hydroxyl equivalent of HNA, HBA and BP)
After the raw materials were charged, the temperature of the reaction system was raised to 140 ° C. and reacted at 140 ° C. for 2 hours. Thereafter, the temperature is further increased to 370 ° C. over 4.7 hours, and then the pressure is reduced to 10 Torr (ie, 1330 Pa) over 15 minutes, and acetic acid, excess acetic anhydride, and other low-boiling components are distilled off. Condensation was performed. After the stirring torque reached a predetermined value, nitrogen was introduced and the pressure was changed from a reduced pressure state to a normal pressure, and the polymer was discharged from the lower part of the polymerization vessel. Moreover, the same evaluation as Example 1 was performed. The evaluation results are shown in Table 1.
原料モノマーの種類、仕込み比率(モル%)を表1及び表2に示す通りとした以外は、実施例1と同様にしてポリマーを得た。また、実施例1と同様の評価を行った。評価結果を表1及び表2に示す。なお、比較例4については、製造時にポリマーが重合容器内で固化し、ポリマーを排出できなかった。 <Examples 4 to 8, Comparative Examples 1 to 8>
A polymer was obtained in the same manner as in Example 1 except that the type of raw material monomer and the charging ratio (mol%) were as shown in Tables 1 and 2. Moreover, the same evaluation as Example 1 was performed. The evaluation results are shown in Tables 1 and 2. In Comparative Example 4, the polymer was solidified in the polymerization vessel during production, and the polymer could not be discharged.
Claims (9)
- 必須の構成成分として、下記構成単位(I)、(II)、及び(III)または(IV)からなり、
全構成単位に対して構成単位(I)の含有量は60~85モル%であり、
全構成単位に対して構成単位(II)の含有量は12~40モル%であり、
全構成単位に対して構成単位(III)または(IV)の含有量は0.1~3モル%であり、
全構成単位に対して構成単位(I)、(II)、及び(III)または(IV)の合計の含有量は100モル%である、
全芳香族ポリエステル。
The content of the structural unit (I) is 60 to 85 mol% with respect to all the structural units,
The content of the structural unit (II) is 12 to 40 mol% with respect to all the structural units,
The content of the structural unit (III) or (IV) is 0.1 to 3 mol% with respect to all the structural units,
The total content of the structural units (I), (II), and (III) or (IV) is 100 mol% with respect to all the structural units.
Totally aromatic polyester.
- 全芳香族ポリエステルの融点よりも10~30℃高い温度における溶融粘度が1000Pa・s以下である、請求項1に記載の全芳香族ポリエステル。 2. The wholly aromatic polyester according to claim 1, which has a melt viscosity of 1000 Pa · s or less at a temperature 10 to 30 ° C. higher than the melting point of the wholly aromatic polyester.
- 全芳香族ポリエステルの融点よりも10~30℃高い温度における溶融粘度が3~500Pa・sである、請求項1または2に記載の全芳香族ポリエステル。 The wholly aromatic polyester according to claim 1 or 2, which has a melt viscosity of 3 to 500 Pa · s at a temperature 10 to 30 ° C higher than the melting point of the wholly aromatic polyester.
- 融点が380℃以下である、請求項1から3のいずれか一項に記載の全芳香族ポリエステル。 The wholly aromatic polyester according to any one of claims 1 to 3, having a melting point of 380 ° C or lower.
- 融点が250~370℃である、請求項1から4のいずれか一項に記載の全芳香族ポリエステル。 The wholly aromatic polyester according to any one of claims 1 to 4, having a melting point of 250 to 370 ° C.
- 結晶化熱量が2.5J/g以上である、請求項1から5のいずれか一項に記載の全芳香族ポリエステル。 The wholly aromatic polyester according to any one of claims 1 to 5, wherein the crystallization heat amount is 2.5 J / g or more.
- [融点-結晶化温度]の値が20℃以上である、請求項1から6のいずれか一項に記載の全芳香族ポリエステル。 The wholly aromatic polyester according to any one of claims 1 to 6, wherein the value of [melting point-crystallization temperature] is 20 ° C or higher.
- 請求項1から7のいずれか一項に記載の全芳香族ポリエステルを含有するポリエステル樹脂組成物。 A polyester resin composition containing the wholly aromatic polyester according to any one of claims 1 to 7.
- 請求項1から8のいずれか一項に記載の全芳香族ポリエステルまたはポリエステル樹脂組成物を成形して得られるポリエステル成形品。 A polyester molded product obtained by molding the wholly aromatic polyester or polyester resin composition according to any one of claims 1 to 8.
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KR1020197020777A KR102120296B1 (en) | 2017-01-26 | 2018-01-22 | All-aromatic polyester and polyester resin composition |
JP2018527815A JP6412296B1 (en) | 2017-01-26 | 2018-01-22 | Totally aromatic polyester and polyester resin composition |
CN201880006958.8A CN110177821B (en) | 2017-01-26 | 2018-01-22 | Wholly aromatic polyester and polyester resin composition |
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WO2020204124A1 (en) * | 2019-04-03 | 2020-10-08 | ポリプラスチックス株式会社 | Wholly aromatic polyester and polyester resin composition |
US20210070927A1 (en) * | 2019-09-10 | 2021-03-11 | Ticona Llc | Polymer Composition and Film for Use in 5G Applications |
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US11912817B2 (en) | 2019-09-10 | 2024-02-27 | Ticona Llc | Polymer composition for laser direct structuring |
US11917753B2 (en) | 2019-09-23 | 2024-02-27 | Ticona Llc | Circuit board for use at 5G frequencies |
WO2022014663A1 (en) * | 2020-07-16 | 2022-01-20 | ポリプラスチックス株式会社 | Resin composition and molded article thereof |
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JP2015174913A (en) * | 2014-03-14 | 2015-10-05 | 上野製薬株式会社 | liquid crystal polyester resin composition |
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KR20190103213A (en) | 2019-09-04 |
JPWO2018139393A1 (en) | 2019-02-07 |
TW201840638A (en) | 2018-11-16 |
KR102120296B1 (en) | 2020-06-08 |
TWI730219B (en) | 2021-06-11 |
CN110177821B (en) | 2020-03-24 |
CN110177821A (en) | 2019-08-27 |
JP6412296B1 (en) | 2018-10-24 |
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