WO2018207774A1 - 全芳香族ポリエステル及びポリエステル樹脂組成物 - Google Patents
全芳香族ポリエステル及びポリエステル樹脂組成物 Download PDFInfo
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- WO2018207774A1 WO2018207774A1 PCT/JP2018/017770 JP2018017770W WO2018207774A1 WO 2018207774 A1 WO2018207774 A1 WO 2018207774A1 JP 2018017770 W JP2018017770 W JP 2018017770W WO 2018207774 A1 WO2018207774 A1 WO 2018207774A1
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- aromatic polyester
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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
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- 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
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- 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
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Definitions
- the present invention relates to a wholly aromatic polyester having high heat stability and good hydrolysis resistance, and a polyester resin composition containing this wholly aromatic polyester.
- Liquid crystalline polymers represented by liquid crystalline polyester resins have excellent fluidity, mechanical strength, heat resistance, chemical resistance, electrical properties, etc. in a well-balanced manner, and are therefore widely used as high-performance engineering plastics. Yes.
- Patent Document 1 discloses an improved method for producing a heat-stable thermotropic liquid crystalline polyester having a predetermined chain length.
- thermal stability is improved by adding a small amount of 1,4-phenylenedicarboxylic acid to liquid crystalline polyester.
- this liquid crystalline polyester is based on 4-hydroxybenzoic acid, there is a problem that there are many decomposition gases.
- Patent Document 2 also discloses a method for producing a heat-stable thermotropic liquid crystalline polyester having a predetermined chain length.
- thermal stability is improved by incorporating a small amount of 2,6-dihydroxynaphthalene or 4,4'-dihydroxybiphenyl into a liquid crystalline polyester.
- this liquid crystalline polyester is also based on 4-hydroxybenzoic acid, there is a problem that there are many decomposition gases.
- Patent Document 3 discloses a liquid crystalline aromatic polyester for insulating material and a resin composition thereof.
- a low dielectric loss tangent is achieved by adding a large amount of 6-hydroxy-2-naphthoic acid to a liquid crystalline aromatic polyester.
- this liquid crystalline aromatic polyester has a problem that it has only a highly reactive hydroxycarboxylic acid composition, has poor thermal stability, and has a large amount of decomposition gas.
- liquid crystalline polyesters are not necessarily sufficient in terms of hydrolysis resistance, and when a polyester molded product obtained by molding a polyester resin composition is used in a humid heat environment such as high temperature and high humidity, hydrolysis is not possible. There is a problem that heat resistance and mechanical strength are remarkably lowered.
- the present invention has been made in order to solve the above-mentioned problems, and is a wholly aromatic polyester having high heat stability, low generation gas having good hydrolysis resistance, high heat stability, and this wholly aroma. It is an object to provide a polyester resin composition containing a group polyester.
- 6-hydroxy-2-naphthoic acid is 60 to 85 mol%
- 4-hydroxybenzoic acid is 12 to 40 mol%
- 1,3-phenylenedicarboxylic acid is 0.1%.
- the present inventors have found that the above-mentioned problems can be solved by using a wholly aromatic polyester comprising ⁇ 3 mol%, and the present inventors have completed the present invention. More specifically, the present invention provides the following.
- 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) is 0.1 to 3 mol% with respect to all the structural units
- the total content of the structural units (I), (II), and (III) is 100 mol% with respect to all the structural units.
- the wholly aromatic polyester according to the present invention comprises the following constituent units (I), (II), and (III) as essential constituent components, and the content of the constituent unit (I) is 60 with respect to all constituent units. Is 85 mol%, the content of the structural unit (II) is 12 to 40 mol% with respect to all the structural units, and the content of the structural unit (III) is 0.1 to 3 with respect to the total structural units. The total content of the structural units (I), (II), and (III) is 100 mol% with respect to all the structural units.
- the structural unit (I) is derived from 6-hydroxy-2-naphthoic acid (hereinafter also referred to as “HNA”).
- the wholly aromatic polyester of the present invention contains 60 to 85 mol% of the structural unit (I) with respect to all the structural units.
- the content of the structural unit (I) is 60 mol% or more, the melting point is not lowered and the heat resistance is not insufficient.
- the content of the structural unit (I) is 85 mol% or less, solidification does not occur during polymerization and a polymer is obtained.
- the content of the structural unit (I) is preferably 63 to 85 mol%, more preferably 63 to 83 mol%, still more preferably 65 to 83 mol%, still more preferably 65 to 80 mol%, and most preferably 68. ⁇ 80 mol%.
- the structural unit (II) is derived from 4-hydroxybenzoic acid (hereinafter also referred to as “HBA”).
- the wholly aromatic polyester of the present invention contains 12 to 40 mol% of the structural unit (II) with respect to the total structural units.
- the content of the structural unit (II) is 12 mol% or more, the polymer does not solidify in the polymerization vessel during production, and the polymer can be discharged.
- the content of the structural unit (II) is 40 mol% or less, the melting point is not lowered and the heat resistance is not insufficient.
- the content of the structural unit (II) is preferably 15 to 40 mol%, more preferably 15 to 35 mol%, still more preferably 18 to 35 mol%, still more preferably 18 to 30 mol%, most preferably 20-30 mol%.
- the structural unit (III) is derived from 1,3-phenylenedicarboxylic acid (hereinafter also referred to as “IA”).
- the wholly aromatic polyester of the present invention contains 0.1 to 3 mol% of the structural unit (III) with respect to all the structural units. Thermal stability does not fall that content of structural unit (III) is 0.1 mol% or less. When the content of the structural unit (III) is 3 mol% or less, the molecular weight (melt viscosity) increases. From the viewpoint of thermal stability and molecular weight, the content of the structural unit (III) is preferably 0.2 to 3 mol%, more preferably 0.2 to 2.5 mol%, still more preferably 0.3 to 2. It is 5 mol%, more preferably 0.3 to 2.0 mol%, and most preferably 0.4 to 2.0 mol%.
- the wholly aromatic polyester of the present invention contains a specific amount of specific structural units (I) to (III) with respect to all the structural units, and therefore generates less gas and has a high thermal stability. In addition to being high, hydrolysis resistance is good.
- the wholly aromatic polyester of the present invention contains 100 mol% of the structural units (I) to (III) in total with respect to all the structural units.
- 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 (III) 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.
- a nematic liquid crystalline polymer causes a significant decrease in viscosity at a melting point or higher, generally exhibiting liquid crystallinity at a melting point or higher is an index of workability.
- the melting point is preferably as high as possible from the viewpoint of heat resistance, but it is preferably 380 ° C. or lower in consideration of thermal deterioration during the melt processing of the polymer, the heating ability of the molding machine, and the like.
- the melting point is more preferably 260 to 370 ° C., further preferably 270 to 370 ° C., still more preferably 270 to 350 ° C., and most preferably 290 to 350 ° C.
- melt viscosity of the wholly aromatic polyester at a temperature 10 to 30 ° C. higher than the melting point of the wholly aromatic polyester of the present invention and a shear rate of 1000 / sec is preferably 1000 Pa ⁇ s or less, more preferably 4 to 500 Pa. ⁇ S, more preferably 4 to 250 Pa ⁇ s.
- melt viscosity means the melt viscosity measured based on ISO11443.
- the total crystallization heat amount of the wholly aromatic polyester of the present invention is preferably 2.3 J / g or more, and more preferably 2.3 to 4.5 J / g.
- the crystallization heat quantity of the polymer determined by differential calorimetry indicating the crystallization state of the polymer is 2.3 J / g or more, the crystallinity is increased and the hydrolysis resistance is improved. Further, it is preferable that the heat of crystallization is 4.5 J / g or less because the toughness is increased.
- 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.
- the value of [melting point ⁇ crystallization temperature] which is a value obtained by subtracting the crystallization temperature from the melting point, is preferably 40 ° C. or more, and preferably 40 to 90 ° C. More preferred.
- the value of [melting point ⁇ crystallization temperature] is within the above range, the wholly aromatic polyester itself or the composition containing the wholly aromatic polyester is easy to ensure fluidity at the time of molding, Filling pressure is unlikely to be excessive.
- 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, etc., or a combination of two or more of these are used, and a melt polymerization method or a combination of a melt polymerization method and a solid phase polymerization method is used. Is preferably 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 potassium acetate, magnesium acetate, stannous acetate, tetrabutyl titanate, lead acetate, sodium acetate, antimony trioxide, tris (2 , 4-pentandionato) cobalt (III) and the like, and organic compound catalysts such as N-methylimidazole and 4-dimethylaminopyridine.
- 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.
- 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
- 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 blended in the polyester resin composition of the present invention 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 polyester resin composition is particularly prominent in improving the heat distortion temperature and mechanical properties.
- 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 and, if necessary, an inorganic or organic filler as essential components, as long as the effects of the present invention are not impaired.
- Other components 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, inflation molding, and the like.
- the polyester molded product formed by molding the wholly aromatic polyester of the present invention is excellent in heat resistance. Moreover, since the polyester molded product formed by shape
- the wholly aromatic polyester and polyester resin composition of the present invention are excellent in moldability and can be processed into various three-dimensional molded products, fibers, films and the like.
- Preferred applications of the polyester molded product of the present invention having the above properties include connectors, CPU sockets, relay switch parts, bobbins, actuators, noise reduction filter cases, electronic circuit boards, or heat fixing rolls for OA equipment. It is done.
- 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.
- 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.
- 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.
- Example 1 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. TA shown in Table 2 represents terephthalic acid.
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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)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)の合計の含有量は100モル%である、
全芳香族ポリエステル。
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)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)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)の合計の含有量は100モル%である。
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。
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。
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。
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)イソフタル酸0.1モル(0.7モル%)(IA)
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。
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。
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。
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。
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。
(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。
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。
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88%以上であれば良好と判断した。
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。
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。なお、表2に記載のTAはテレフタル酸を示す。
Claims (9)
- 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。
- 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4~500Pa・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。
- 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。
- 融点が260~370℃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。
- 結晶化熱量が2.3J/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。
- [融点-結晶化温度]の値が40℃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。
- 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。
- 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。
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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 |
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CN113767134B (zh) * | 2019-04-03 | 2024-02-09 | 宝理塑料株式会社 | 全芳香族聚酯和聚酯树脂组合物 |
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KR20190115101A (ko) | 2019-10-10 |
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