WO2014185739A1 - 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 - Google Patents
신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 Download PDFInfo
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- WO2014185739A1 WO2014185739A1 PCT/KR2014/004394 KR2014004394W WO2014185739A1 WO 2014185739 A1 WO2014185739 A1 WO 2014185739A1 KR 2014004394 W KR2014004394 W KR 2014004394W WO 2014185739 A1 WO2014185739 A1 WO 2014185739A1
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- acid dianhydride
- polyimide
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- VKZRWSNIWNFCIQ-UHFFFAOYSA-N OC(CC(C(O)=O)NCCNC(CC(O)=O)C(O)=O)=O Chemical compound OC(CC(C(O)=O)NCCNC(CC(O)=O)C(O)=O)=O VKZRWSNIWNFCIQ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
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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
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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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
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3719—Polyamides or polyimides
Definitions
- the present invention relates to novel acid dianhydrides, methods for their preparation and polyimides prepared therefrom.
- polyimides have high mechanical strength, heat resistance, insulation, solvent resistance, and the like, and thus are widely used as electronic materials such as protective materials, insulating materials, and color filters in liquid crystal display devices and semiconductors.
- optical communication materials such as optical waveguide materials and use as substrates for mobile phones are also expected.
- polyimide that is not only excellent in heat resistance and solvent resistance but also has a large number of performances depending on the application such as transparency is desired.
- the wholly aromatic polyimide obtained by the polycondensation reaction of the aromatic tetracarboxylic dianhydride and aromatic diamine which is conventionally used generally has a dark amber color, there exists a problem in the use which requires high transparency.
- the wholly aromatic polyimide is insoluble in the organic solvent, it is necessary to actually dehydrate and ring-close the polyamic acid which is its precursor by heat.
- a polyimide precursor is obtained by polycondensation reaction of an alicyclic tetracarboxylic dianhydride and an aromatic diamine, and imidation of the precursor results in relatively less coloring and highly transparent polyimide. It is known to obtain (Japanese Patent Laid-Open No. 2-24294, Japanese Patent Laid-Open No. 58-208322).
- polyamic acid and polyimide made from unsubstituted alicyclic tetracarboxylic dianhydride as a raw material are soluble only in polar organic solvents having low solubility in general organic solvents and high boiling points.
- high temperature is required at the time of film forming baking, and it has an undesirable effect on the other organic substance which comprises an organic electroluminescent element.
- organic electroluminescent element gas As a barrier film is examined (Japanese Patent Laid-Open No. 2006-232960).
- the polyimide has room for improvement in view of low polymerization degree and heat resistance, and it is not necessarily sufficient for solubility in organic solvents.
- the main object of the present invention is to prepare a novel acid dianhydride which is used as a raw material monomer of a polyimide that exhibits excellent thermal stability and low permittivity while maintaining the excellent physical properties of the polyimide, and has excellent solubility and light transmittance in an organic solvent. To provide a method.
- the present invention also provides a polyamic acid characterized by containing the novel acid dianhydride and a polyimide obtained by dehydrating and closing the polyamic acid.
- one embodiment of the present invention provides an acid dianhydride represented by the following formula (1).
- Another embodiment of the present invention comprises the steps of (a) N-alkylation of the compound represented by Formula 2 in the presence of a base catalyst to obtain a compound represented by Formula 3; And (b) it provides a method for producing an acid dianhydride comprising the step of preparing an acid dianhydride represented by the following formula 1 by the dehydration ring-closure reaction in the presence of a dehydrating agent in the compound represented by the formula (3).
- the base catalyst of step (a) may be characterized in that at least one selected from the group consisting of potassium hydroxide, sodium hydroxide, barium hydroxide, calcium hydroxide, aluminum hydroxide and magnesium hydroxide.
- the dehydration ring closure of step (b) may be characterized in that it is carried out for 4 to 28 hours at 40 ⁇ 100 °C.
- the dehydrating agent of step (b) may be characterized in that the addition of 2 to 10 moles with respect to 1 mole of the compound represented by the formula (3).
- the dehydrating agent of step (b) may be characterized in that at least one selected from the group consisting of acetic anhydride, pyridine, isoquinoline and tertiary amine.
- Another embodiment of the present invention provides a polyamic acid obtained by reacting an acid dianhydride and diamine represented by the following Chemical Formula 1.
- Another embodiment of the present invention provides a polyimide, which is obtained by dehydrating and closing the polyamic acid.
- the polyimide of this invention is colorless, transparent, and excellent in thermal stability, and it has low dielectric constant, and uses are used as optical communication materials, such as electronic materials, optical waveguides, such as protective materials in liquid crystal display elements, semiconductors, and insulating materials. .
- the present invention relates to an acid dianhydride represented by the following general formula (1) in one aspect.
- the present invention provides a process for preparing a compound represented by the following formula: (a) N-alkylation of a compound represented by Formula 2 in the presence of a base catalyst; And (b) dehydrating cyclization of the compound represented by Chemical Formula 3 in the presence of a dehydrating agent to produce an acid dianhydride represented by the following Chemical Formula 1.
- aliphatic polyimides have high transparency and low dielectric constant due to their low molecular weight, bipolarity, and low intermolecular or intramolecular charge transfer properties compared to aromatic polyimides. Is getting.
- N-acetylated-1,2-ethylenediamine-succinic anhydride (N-acetylated-1,2-) containing nitrogen to prepare aliphatic polyimide having high transparency and low permittivity characteristics ethylenediamine-disuccinic anhydride: an acid dianhydride represented by Formula 1) is synthesized.
- Acid dianhydride represented by the formula (1) according to the present invention contains one or more nitrogen atoms in the molecule, thereby causing the interaction of the intramolecular or intermolecular chain due to the isolated electron pair of the nitrogen atom, thereby using the intrinsic polyimide It is possible to greatly improve the solubility and mechanical strength of the polyimide while maintaining its excellent properties.
- Acid dianhydride according to the present invention can be prepared simply and easily in two stages, alkylation reaction and dehydration ring closure reaction.
- the compound represented by Chemical Formula 3 is produced by N-alkylation of the compound represented by Chemical Formula 2 in the presence of a base catalyst, and then the compound represented by Chemical Formula 3 is produced. Dehydration ring closure in the presence of a dehydrating agent to prepare an acid dianhydride represented by the formula (1).
- the compound represented by Formula 3 is obtained by N-alkylation of the compound represented by Formula 2 (L-aspartic acid) in the presence of a base catalyst.
- the base catalyst used in the N-alkalization reaction may be at least one selected from the group consisting of potassium hydroxide, sodium hydroxide, barium hydroxide, calcium hydroxide, aluminum hydroxide and magnesium hydroxide in terms of price and ease of handling, It can be freely selected and used according to the ion conversion and exchange rate.
- reaction material itself as a solvent as the reaction mode
- other reaction solvents may be used.
- the reaction solvent is not particularly limited as long as it does not inhibit the reaction, and examples thereof include 1,4-dioxane, toluene, NMP (N-Methyl-2-pyrrolidone), DMAc (dimethylacetamide), and 1,2-dibromo. Ethane and the like.
- the compound represented by Chemical Formula 3 thus produced is introduced with a dehydrating agent to prepare an aliphatic acid dianhydride represented by Chemical Formula 1 by a dehydration ring closure reaction.
- the dehydration ring-closure reaction is carried out for 4 to 28 hours at 40 ⁇ 100 °C, if more than 100 °C or 28 hours when the yield is reduced due to the evaporation of the catalyst and solvent, the reaction proceeds below 40 °C In this case, the reaction time may be increased or the yield may be lowered due to insufficient reaction.
- the dehydrating agent may be at least one selected from the group consisting of tertiary amines such as acetic anhydride, pyridine, isoquinoline, triethylamine and the like, and in terms of efficiency, it is preferable to use acetic anhydride and / or pyridine.
- the content of the dehydrating agent may be 2 moles or more, with respect to 1 mole of the compound represented by Formula 3, preferably 2 to 10 moles.
- the dehydrating agent is used in less than 2 moles with respect to 1 mole of the compound represented by the formula (3), the reaction does not sufficiently occur, so that the yield is lowered. have.
- the resultant compound is filtered by a conventional method and then dried to prepare an acid dianhydride represented by the formula (1).
- the present invention relates to a polyamic acid obtained by reacting an acid dianhydride represented by the following formula (1) with a diamine.
- the present invention relates to a polyimide obtained by dehydrating and closing the polyamic acid.
- the acid dianhydride represented by the general formula (1) of the present invention described above may be prepared into a polyimide by preparing a polyamic acid by diamine and a polycondensation reaction, followed by dehydration ring closure using heat or a catalyst.
- the said diamine is not specifically limited, Various diamines conventionally used for polyimide synthesis can be used. Specific examples thereof include p-phenylenediamine, m-phenylenediamine, 2,5-diaminotoluene, 2,6-diaminotoluene, 1,3-bis (4,4'-aminophenoxy) benzene, 4 , 4'-diamino-1,5-phenoxypentane, 4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dimethoxy- 4,4'-diaminobiphenyl, 4,4'-diaminodiphenylether, 4,4'-diaminodiphenylmethane, 2,2'-diaminodiphenylpropane, bis (3,5-di Ethyl-4-aminophenyl) methane, diaminodiphen
- the method for obtaining the polyamic acid of the present invention is not particularly limited, and the acid dianhydride represented by the general formula (1) and the diamine may be reacted and polymerized by a known production method, but the aliphatic dianhydride represented by the general formula (1) in an organic solvent.
- the method of mixing and reacting a lide compound and a diamine is simple.
- organic solvent used examples include m-cresol, N-methyl-2-pyrrolidone (NMP), N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAc), N-methyl caprolactam, dimethyl sulfoxide (DMSO), tetramethyl urea, pyridine, dimethyl sulfone, hexamethylphosphoramide, gamma -butyrolactone, etc. are mentioned. These solvents may be used alone or in combination of two or more thereof. Moreover, even if it is a solvent which does not melt a polyamic acid, you may add to and use the said solvent within the range from which a uniform solution is obtained.
- the reaction temperature of solution polymerization can select arbitrary temperature of -20-150 degreeC, Preferably -5-100 degreeC.
- the molecular weight of a polyamic acid can be controlled by changing the molar ratio of the acid dianhydride represented by General formula (1) used for reaction, and diamine, and similar to a normal polycondensation reaction, the polya produced as this molar ratio approaches 1, The molecular weight of the acid is increased.
- the polyimide of this invention is obtained by dehydrating and ring-closing the polyamic acid obtained by making it above.
- the rate of change (dehydration closure rate) from polyamic acid to polyimide is defined as the imidization rate, but the imidation rate of the polyimide of the present invention is not limited to 100%, and optionally 1 to 100%. You can select the value of.
- the method of dehydrating and ring-closing the polyamic acid is not particularly limited, but similarly to the conventional polyamic acid, a ring closure by heating or a chemical ring closure using a known dehydration ring-closure catalyst can be employed.
- the method by the said heating can be performed at arbitrary temperature of 100-300 degreeC, Preferably it is 120-250 degreeC.
- the method of chemically ring closing can be performed in presence of organic bases, such as a pyridine and a triethylamine, and acetic anhydride, etc., and the temperature at this time can select arbitrary temperature of -20-200 degreeC.
- organic bases such as a pyridine and a triethylamine, and acetic anhydride, etc.
- the polymerization solution of polyamic acid can be used as it is or diluted.
- an organic solvent at this time the polymerization solvent of the polyamic acid mentioned above is mentioned.
- the polyimide (containing) solution thus obtained may be used as it is, or a solvent such as methanol or ethanol may be added to precipitate the polymer, which is isolated and re-dissolved as a powder or in a suitable solvent for use. Can be.
- the solvent for re-dissolution is not particularly limited as long as it dissolves the obtained polymer.
- m-cresol, 2-pyrrolidone, NMP, N-ethyl-2-pyrrolidone, and N-vinyl-2-pyrroli DON, DMAc, DMF, (gamma) -butyrolactone, etc. are mentioned.
- 50.73 g (0.38 mol) of the compound represented by the formula (2) is mixed with 30 ml (50% aqueous solution) of potassium hydroxide, 13.94 g (0.19 mol) of potassium hydroxide, and 70 ml of distilled water to a 1 liter three-necked flask.
- the flask was equipped with a condenser, a 50 ml isostatic dropping funnel, a reflux condenser and a magnetic stirrer. 28 ml of 1,2-dibromoethane (50% aqueous solution) was added through the third neck of the flask with caution, and then heated to reflux to 60 ° C., dropping potassium hydroxide (24 ml, 50% aqueous solution) for 6 hours.
- the melting point (Buchi, M-560) was measured, NMR ( 1 H and 13 C) (JEOL, JNM-LA400) and IR (AVATAR, 360 FT-IR) Were respectively measured.
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Abstract
Description
Claims (8)
- 제2항에 있어서, 상기 (a) 단계의 염기촉매는 수산화칼륨, 수산화나트륨, 수산화바륨, 수산화칼슘, 수산화알루미늄 및 수산화마그네슘으로 구성된 군에서 선택되는 1종 이상인 것을 특징으로 하는 산 이무수물의 제조방법.
- 제2항에 있어서, 상기 (b) 단계의 탈수 폐환반응은 40 ~ 100℃에서 4 ~ 28시간 동안 수행하는 것을 특징으로 하는 산 이무수물의 제조방법.
- 제2항에 있어서, 상기 (b) 단계의 탈수제는 화학식 3으로 표시되는 화합물 1몰에 대하여, 2 ~ 10몰로 투입하는 것을 특징으로 하는 산 이무수물의 제조방법.
- 제2항에 있어서, 상기 (b) 단계의 탈수제는 무수 아세트산, 피리딘, 이소퀴놀린 및 3차 아민으로 구성된 군에서 선택되는 1종 이상인 것을 특징으로 하는 산 이무수물의 제조방법.
- 제7항의 폴리아믹산을 탈수 폐환시켜 얻어지는 것을 특징으로 하는 폴리이미드.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP14797631.0A EP2998302B1 (en) | 2013-05-16 | 2014-05-16 | Novel acid dianhydride, method for preparing same, and polyimide prepared therefrom |
CN201480028547.0A CN105246886A (zh) | 2013-05-16 | 2014-05-16 | 新型酸二酐、其制备方法以及由此制备的聚酰亚胺 |
JP2016513878A JP6196731B2 (ja) | 2013-05-16 | 2014-05-16 | 新規酸二無水物、この製造方法、及びこれから製造されたポリイミド |
US14/890,658 US9676739B2 (en) | 2013-05-16 | 2014-05-16 | Acid dianhydride, method for preparing same, and polyimide prepared therefrom |
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KR10-2013-0055392 | 2013-05-16 | ||
KR1020130055392A KR101595614B1 (ko) | 2013-05-16 | 2013-05-16 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
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WO2014185739A1 true WO2014185739A1 (ko) | 2014-11-20 |
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US (1) | US9676739B2 (ko) |
EP (1) | EP2998302B1 (ko) |
JP (1) | JP6196731B2 (ko) |
KR (1) | KR101595614B1 (ko) |
CN (1) | CN105246886A (ko) |
HU (1) | HUE037322T2 (ko) |
WO (1) | WO2014185739A1 (ko) |
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KR101615431B1 (ko) * | 2014-05-15 | 2016-04-25 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
Citations (7)
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US4290960A (en) * | 1979-03-15 | 1981-09-22 | Basf Aktiengesellschaft | Preparation of 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one |
JPS58208322A (ja) | 1982-05-31 | 1983-12-05 | Japan Synthetic Rubber Co Ltd | ポリイミド化合物の製造方法 |
JPH0224294B2 (ko) | 1984-03-09 | 1990-05-29 | Nissan Chemical Ind Ltd | |
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GB9322648D0 (en) | 1993-11-03 | 1993-12-22 | Ass Octel | Process for the production of s.s.e.d.d.s |
US5466867A (en) * | 1994-07-11 | 1995-11-14 | Albemarle Corporation | Method for producing [S,S]-ethylenediamine-N,N'-disuccinic acid from its calcium salt |
US6103322A (en) * | 1998-12-23 | 2000-08-15 | Elsicon Inc. | Materials for inducing alignment of liquid crystals and liquid crystal optical elements |
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2013
- 2013-05-16 KR KR1020130055392A patent/KR101595614B1/ko active IP Right Grant
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2014
- 2014-05-16 WO PCT/KR2014/004394 patent/WO2014185739A1/ko active Application Filing
- 2014-05-16 JP JP2016513878A patent/JP6196731B2/ja active Active
- 2014-05-16 EP EP14797631.0A patent/EP2998302B1/en active Active
- 2014-05-16 US US14/890,658 patent/US9676739B2/en active Active
- 2014-05-16 CN CN201480028547.0A patent/CN105246886A/zh active Pending
- 2014-05-16 HU HUE14797631A patent/HUE037322T2/hu unknown
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Also Published As
Publication number | Publication date |
---|---|
HUE037322T2 (hu) | 2018-08-28 |
US9676739B2 (en) | 2017-06-13 |
CN105246886A (zh) | 2016-01-13 |
EP2998302B1 (en) | 2018-04-04 |
EP2998302A1 (en) | 2016-03-23 |
JP2016520078A (ja) | 2016-07-11 |
KR20140135341A (ko) | 2014-11-26 |
US20160108014A1 (en) | 2016-04-21 |
KR101595614B1 (ko) | 2016-02-18 |
JP6196731B2 (ja) | 2017-09-13 |
EP2998302A4 (en) | 2017-01-11 |
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