WO2012011664A2 - 방향족 액정 폴리에스테르 수지의 제조방법 및 방향족 액정 폴리에스테르 수지 컴파운드의 제조방법 - Google Patents
방향족 액정 폴리에스테르 수지의 제조방법 및 방향족 액정 폴리에스테르 수지 컴파운드의 제조방법 Download PDFInfo
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- WO2012011664A2 WO2012011664A2 PCT/KR2011/004325 KR2011004325W WO2012011664A2 WO 2012011664 A2 WO2012011664 A2 WO 2012011664A2 KR 2011004325 W KR2011004325 W KR 2011004325W WO 2012011664 A2 WO2012011664 A2 WO 2012011664A2
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- liquid crystal
- aromatic
- polyester resin
- aromatic liquid
- crystal 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
- C08G63/78—Preparation processes
- C08G63/80—Solid-state polycondensation
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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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/065—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids the hydroxy and carboxylic ester 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
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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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing 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
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
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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
- C08G63/78—Preparation processes
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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
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3804—Polymers with mesogenic groups in the main chain
- C09K19/3809—Polyesters; Polyester derivatives, e.g. polyamides
Definitions
- a method for producing an aromatic liquid crystal polyester resin and a method for producing an aromatic liquid crystal polyester resin compound are disclosed. More specifically, acetylating a first monomer having an amino group, acetylating a second monomer having a hydroxyl group but not containing an amino group, and polycondensing the acetylated monomers with an aromatic dicarboxylic acid
- a method for producing an aromatic liquid crystal polyester resin comprising the step of reacting and synthesizing an aromatic liquid crystal polyester prepolymer and a method for producing an aromatic liquid crystal polyester resin compound using the aromatic liquid crystal polyester resin prepared by the method are disclosed. .
- the aromatic liquid crystal polyester resin exhibits a behavior in which the molecules are rigid, form a liquid crystal state without intermolecular entanglement even in the molten state, and the molecular chains are oriented in the flow direction by the shear force during molding.
- the synthesized aromatic polyester resin does not have uniform physical properties as a whole.
- the aromatic polyester resin compound and its molded article also do not have uniform physical properties as a whole, which lowers the physical properties of the resin compound such as mechanical strength, and blisters when the molded article is left in hot air or liquid for a long time. There is a problem that occurs.
- One embodiment of the present invention is the step of acetylating the first monomer having an amino group, acetylating the second monomer having a hydroxyl group but does not include an amino group, and the acetylated monomers and aromatic dicarboxylic acid It provides a method for producing an aromatic liquid crystal polyester resin comprising the step of polycondensation reaction to synthesize an aromatic liquid crystal polyester prepolymer.
- Another embodiment of the present invention provides a method for producing an aromatic liquid crystal polyester resin compound using the aromatic liquid crystal polyester resin prepared by the method for producing an aromatic liquid crystal polyester resin.
- It provides a method for producing an aromatic liquid crystal polyester resin comprising the step of polycondensation reaction of the acetylated first monomer, the acetylated 2 monomer and dicarboxylic acid to synthesize an aromatic liquid crystal polyester prepolymer.
- the method for preparing the aromatic liquid crystal polyester resin may further include synthesizing the aromatic liquid crystal polyester resin by solid-phase polycondensation of the synthesized aromatic liquid crystal polyester prepolymer.
- the amount of the carboxylic acid anhydride may be 2.0 to 4.0 mol parts based on 1 mol part of the sum of the amino group and the hydroxyl group included in the first monomer.
- the first monomer may include at least one compound selected from the group consisting of aromatic hydroxylamine, aliphatic hydroxylamine, aromatic diamine, aliphatic diamine, aromatic amino carboxylic acid and aliphatic amino carboxylic acid.
- the aromatic hydroxylamine includes at least one compound selected from the group consisting of 3-aminophenol, 4-aminophenol and 2-amino-6-naphthol, and the aliphatic hydroxylamine is 3-aminopropanol, 4- At least one compound selected from the group consisting of aminobutanol and 5-aminopentanol, wherein the aromatic diamine is a group consisting of 1,4-phenylene diamine, 1,3-phenylene diamine and 2,6-naphthalene diamine At least one compound selected from, wherein the aliphatic diamine comprises at least one compound selected from the group consisting of 1,4-diaminobutane, 1,5-diaminopentane and 1,6-diaminohexane Wherein the aromatic amino carboxylic acid is at least one selected from the group consisting of 4-aminobenzoic acid, 2-amino-naphthalene-6-carboxylic acid and 4-amino-biphenyl-4-car
- the second monomer may comprise at least one compound selected from the group consisting of aromatic diols and aromatic hydroxy carboxylic acids.
- the aromatic diol is selected from the group consisting of biphenol, hydroquinone, 1,4-dihydroxy naphthalene and 2,6-dihydroxy naphthalene
- At least one compound, and the aromatic hydroxy carboxylic acid may comprise at least one compound of para hydroxy benzoic acid and 6-hydroxy-2-naphthoic acid.
- the dicarboxylic acid is selected from the group consisting of isophthalic acid, naphthalene dicarboxylic acid, terephthalic acid, 1,3-propanedicarboxylic acid, 1,4-butanedicarboxylic acid and 1,5-pentanedicarboxylic acid At least one compound may be included.
- Acetylation of the first monomer and acetylation of the second monomer may be performed for 1 to 3 hours at a temperature range of 140 ⁇ 160 °C.
- Synthesis of the aromatic liquid crystal polyester prepolymer may be performed for 5-8 hours in the temperature range of 310 ⁇ 340 °C.
- the first monomer, the second monomer, and the dicarboxylic acid may each be an aromatic compound.
- Method for producing an aromatic liquid crystal polyester resin is a step of acetylating a first monomer having an amino group with a carboxylic anhydride (acetylation step of the first monomer), having a hydroxyl group but having an amino group Reacting with a second carboxylic acid anhydride, which is not included, to further acetylate (acetylation of the second monomer) and condensation of the acetylated first monomer, the acetylated 2 monomer and dicarboxylic acid. Synthesizing the aromatic liquid crystal polyester prepolymer.
- an acetyl group (-COCH 3 ) is introduced into the amino group (-NH 2 ) included in the first monomer to form an acetylamino group (-NHCOCH 3 ), and acetic acid is produced as a by-product.
- the byproduct acetic acid can be removed from the product in gaseous state.
- the amino group included in the first monomer is used in the reaction with acetic acid rather than in the acetylation reaction to form ammonium ions. Will increase production. As a result, a large amount of bubbles are generated on the surface of the product during the subsequent polycondensation reaction. Therefore, after the amino group contained in the first monomer is converted to the acetyl group under the condition of minimizing the generation of bubbles, the acetylation step of the second monomer after the acetylation step of the first monomer in order to be able to participate in the polycondensation reaction Will proceed.
- the amount of bubbles generated on the surface of the product during the polycondensation reaction can be reduced to prevent the byproduct removal column from being closed, and the amount of gaseous by-products contained in the product is also reduced.
- the aromatic liquid-crystalline polyester resin, its resin compound, and molded object which have the uniformity and excellent physical property as a whole can be manufactured.
- the aromatic hydroxylamine may include at least one compound selected from the group consisting of 3-aminophenol, 4-aminophenol and 2-amino-6-naphthol.
- the aromatic amino carboxylic acid may include at least one compound selected from the group consisting of 4-aminobenzoic acid, 2-amino-naphthalene-6-carboxylic acid and 4-amino-biphenyl-4-carboxylic acid. .
- the aliphatic amino carboxylic acid is at least one selected from the group consisting of 4-aminobutanoic acid, 5-aminopentanoic acid, and 6-aminohexanoic acid. It may include a compound.
- acetyl group (-COCH 3) is introduced to hydroxyl group (-OH) contained in the second monomer to form the acetyl oxy group (-OCOCH 3), and acetic acid gas is produced as a by-product do.
- the byproduct acetic acid gas can be easily removed from the product.
- the second monomer may comprise at least one compound selected from the group consisting of aromatic diols, aromatic hydroxy carboxylic acids and aliphatic hydroxy carboxylic acids.
- the aromatic diol may comprise at least one compound of biphenols and hydroquinones.
- the aromatic hydroxy carboxylic acid may comprise at least one compound of para hydroxy benzoic acid and 2-hydroxy-6-naphthoic acid.
- the additional carboxylic anhydride may comprise at least one compound selected from the group consisting of acetic anhydride, diphenyl carbonate and benzyl acetate.
- the polycondensation reaction of the acetylated first monomer, the acetylated 2 monomer, and dicarboxylic acid to synthesize an aromatic liquid crystal polyester prepolymer may be performed by solution polycondensation or bulk condensation polymerization. have.
- the dicarboxylic acid is selected from the group consisting of isophthalic acid, naphthalene dicarboxylic acid, terephthalic acid, 1,3-propanedicarboxylic acid, 1,4-butanedicarboxylic acid and 1,5-pentanedicarboxylic acid At least one compound may be included.
- metal acetate may be additionally used as a catalyst for promoting the reaction in the synthesis of the aromatic liquid crystal polyester prepolymer.
- the metal acetate catalyst may include at least one selected from the group consisting of magnesium acetate, potassium acetate, calcium acetate, zinc acetate, manganese acetate, lead acetate, antimony acetate, and cobalt acetate.
- the amount of the metal acetate catalyst used may be, for example, 0.10 parts by weight or less based on 100 parts by weight of the total amount of the first monomer and the second monomer.
- Synthesis of the aromatic liquid crystal polyester prepolymer may be performed for 5-8 hours in the temperature range of 310 ⁇ 340 °C. When the temperature and time are respectively within the above range, no discharge process failure occurs after the polycondensation reaction, and an aromatic liquid crystal polyester copolymer suitable for the solid state polycondensation reaction can be obtained.
- the method for producing an aromatic liquid crystal polyester resin may further comprise the step of synthesizing the aromatic liquid crystal polyester resin by solid-phase polycondensation of the aromatic liquid crystal polyester prepolymer.
- the heat providing method may include a method using a heating plate, a method using a hot air, a method using a high temperature fluid, and the like.
- purging with an inert gas or vacuum removal can be performed.
- aromatic liquid crystal polyester resin produced by the above method includes various repeating units in the chain, and may include, for example, the following repeating units:
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Abstract
Description
구분 | 공정장애 | 수지의 물성 | 수지 컴파운드의 용융점도(poise) | 사출 성형품의 물성 | |||||
용융점도(poise) | 용융온도(℃) | 인장강도(MPa) | 굴곡강도(MPa) | 충격강도(J/m) | 내열온도(℃) | 블리스터발생여부(발생: ○, 미발생:×) | |||
실시예 1 | 無 | 390 | 334 | 360 | 115 | 142 | 850 | 265 | × |
실시예 2 | 無 | 380 | 334 | 355 | 117 | 145 | 880 | 267 | × |
비교예 1 | 有 | 180 | 323 | 95 | 102 | 118 | 480 | 254 | ○ |
Claims (13)
- 아미노기를 갖는 제1 단량체를 카르복실산 무수물과 반응시켜 아세틸화하는 단계;수산기를 갖되 아미노기를 포함하지 않는 제2 단량체를 추가 카르복실산 무수물과 반응시켜 아세틸화하는 단계; 및상기 아세틸화된 제1 단량체, 상기 아세틸화된 2 단량체 및 디카르복실산을 중축합 반응시켜 방향족 액정 폴리에스테르 프리폴리머를 합성하는 단계를 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 합성된 방향족 액정 폴리에스테르 프리폴리머를 고상 중축합함으로써 방향족 액정 폴리에스테르 수지를 합성하는 단계를 추가로 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 카르복실산 무수물의 사용량은 상기 제1 단량체에 포함된 아미노기와 수산기의 합 1몰부에 대하여 2.0~4.0몰부인 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 제1 단량체는 방향족 히드록실아민, 지방족 히드록실아민, 방향족 디아민, 지방족 디아민, 방향족 아미노 카르복실산 및 지방족 아미노 카르복실산으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제4항에 있어서,상기 방향족 히드록실아민은 3-아미노페놀, 4-아미노페놀 및 2-아미노-6-나프톨로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하고, 상기 지방족 히드록실아민은 3-아미노프로판올, 4-아미노부탄올 및 5-아미노펜탄올로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하며, 상기 방향족 디아민은 1,4-페닐렌 디아민, 1,3-페닐렌 디아민 및 2,6-나프탈렌 디아민으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하고, 상기 지방족 디아민은 1,4-디아미노부탄, 1,5-디아미노펜탄 및 1,6-디아미노헥산으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하며, 상기 방향족 아미노 카르복실산은 4-아미노벤조산, 2-아미노-나프탈렌-6-카르복실산 및 4-아미노-바이페닐-4-카르복실산으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하고, 상기 지방족 아미노 카르복실산은 4-아미노부타노산, 5-아미노펜타노산 및 6-아미노헥사노산으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 제2 단량체는 방향족 디올, 방향족 히드록시 카르복실산 및 지방족 히드록시 카르복실산으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제6항에 있어서,상기 방향족 디올은 바이페놀, 하이드로퀴논, 1,4-디히드록시 나프탈렌 및 2,6-디히드록시 나프탈렌으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하고, 상기 방향족 히드록시 카르복실산은 파라 히드록시 벤조산 및 6-히드록시-2-나프토산 중 적어도 1종의 화합물을 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 카르복실산 무수물 및 추가 카르복실산 무수물은, 각각 독립적으로, 아세트산 무수물, 디페닐 카보네이트 및 벤질 아세테이트로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 디카르복실산은 이소프탈산, 나프탈렌 디카르복실산, 테레프탈산, 1,3-프로판디카르복실산, 1,4-부탄디카르복실산 및 1,5-펜탄디카르복실산으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 제1 단량체의 아세틸화 단계 및 상기 제2 단량체의 아세틸화 단계는, 각각 독립적으로, 140~160℃의 온도 범위에서 1~3시간 동안 진행되는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 방향족 액정 폴리에스테르 프리폴리머의 합성단계는 310~340℃의 온도 범위에서 5~8시간 동안 진행되는 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항에 있어서,상기 제1 단량체, 제2 단량체 및 디카르복실산은 각각 방향족 화합물인 방향족 액정 폴리에스테르 수지의 제조방법.
- 제1항 내지 제12항 중 어느 한 항의 방법에 따라 제조된 방향족 액정 폴리에스테르 수지를 사용하는 방향족 액정 폴리에스테르 수지 컴파운드의 제조방법.
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EP11809791.4A EP2597109B1 (en) | 2010-07-20 | 2011-06-14 | Method for preparing an aromatic liquid crystal polyester resin and method for preparing a compound of aromatic liquid crystal polyester resin |
CN201180035325.8A CN103003330B (zh) | 2010-07-20 | 2011-06-14 | 芳香族液晶聚酯树脂的制造方法及芳香族液晶聚酯树脂复合物的制造方法 |
US13/810,884 US9012593B2 (en) | 2010-07-20 | 2011-06-14 | Method for preparing an aromatic liquid crystal polyester resin and method for preparing a compound of aromatic liquid crystal polyester resin |
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CN110527070B (zh) * | 2019-08-01 | 2021-08-27 | 南京清研高分子新材料有限公司 | 一种一锅法制备tlcp的方法 |
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KR20120009705A (ko) | 2012-02-02 |
CN103003330A (zh) | 2013-03-27 |
CN103003330B (zh) | 2015-04-29 |
JP5970455B2 (ja) | 2016-08-17 |
EP2597109B1 (en) | 2017-05-31 |
US9012593B2 (en) | 2015-04-21 |
TWI515222B (zh) | 2016-01-01 |
JP2013531125A (ja) | 2013-08-01 |
WO2012011664A3 (ko) | 2012-05-03 |
EP2597109A4 (en) | 2014-01-15 |
TW201206986A (en) | 2012-02-16 |
EP2597109A2 (en) | 2013-05-29 |
US20130116397A1 (en) | 2013-05-09 |
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