WO2015108167A1 - Procédé de production de dérivé acide cyclobutane tétracarboxylique - Google Patents

Procédé de production de dérivé acide cyclobutane tétracarboxylique Download PDF

Info

Publication number
WO2015108167A1
WO2015108167A1 PCT/JP2015/051146 JP2015051146W WO2015108167A1 WO 2015108167 A1 WO2015108167 A1 WO 2015108167A1 JP 2015051146 W JP2015051146 W JP 2015051146W WO 2015108167 A1 WO2015108167 A1 WO 2015108167A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
production method
maleic anhydride
reaction
electron withdrawing
Prior art date
Application number
PCT/JP2015/051146
Other languages
English (en)
Japanese (ja)
Inventor
淳平 島田
近藤　光正
Original Assignee
日産化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Priority to CN201580004875.1A priority Critical patent/CN105916867A/zh
Priority to KR1020167018451A priority patent/KR20160108335A/ko
Priority to KR1020217025078A priority patent/KR20210100756A/ko
Priority to KR1020227015850A priority patent/KR102653978B1/ko
Priority to JP2015557901A priority patent/JP6565686B2/ja
Publication of WO2015108167A1 publication Critical patent/WO2015108167A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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
    • 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
    • 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
    • C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
    • C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers

Definitions

  • the present invention relates to a method for producing an alicyclic tetracarboxylic dianhydride that can be a raw material monomer such as polyimide for optical materials.
  • a polyimide resin is widely used as an electronic material such as a protective material or an insulating material in a liquid crystal display element or a semiconductor because of its high mechanical strength, heat resistance, insulation, solvent resistance, and the like.
  • an optical communication material such as an optical waveguide material is also expected.
  • the development of this field has been remarkable, and correspondingly, higher and higher properties are required for the materials used. That is, it is expected not only to be excellent in heat resistance and solvent resistance, but also to have a large number of performances depending on the application.
  • Patent Document 3 shows the following scheme.
  • 1,3-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid-1,2: 3,4-dianhydride is obtained by photodimerization reaction of citraconic anhydride (abbreviated as MMA).
  • MMA citraconic anhydride
  • Product (1,3-DMCBDA) and 1,2-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid-1,2: 3,4-dianhydride (1,2-DMCBDA) Is disclosed.
  • 1,3-DMCBDA when 1,3-DMCBDA is compared with 1,2-DMCBDA, the former 1,3-DMCBDA, which is an isomer having a highly symmetric structure, has a molecular weight higher than that of the latter 1,2-DMCBDA. It is known that a high polyimide can be produced and is more useful.
  • Patent Document 3 describes that a mixture of 1,3-DMCBDA and 1,2-DMCBDA can be obtained, the former is a highly useful isomer having a highly symmetric structure. There is no description on the selective and high yield production of 1,3-DMCBDA.
  • Japanese Patent Publication No. 2-24294 Japanese Unexamined Patent Publication No. 58-208322 Japanese Unexamined Patent Publication No. 4-106127
  • the object of the present invention is to use 1,2-dialkylcyclobutane-1,2,3,4-tetracarboxylic acid-1,2 by a photodimerization reaction using a specific maleic anhydride compound as a raw material, as compared with the conventional method.
  • 1,3-dialkylcyclobutane-1,2, which is a highly useful isomer having a highly symmetric structure than 3,4-dianhydride hereinafter also referred to as 1,2-DACBDA
  • Novel production capable of improving the selectivity of 3,4-tetracarboxylic acid-1,2 3,4-dianhydride (hereinafter also referred to as 1,3-DACBDA) and producing it in high yield It is to provide a method.
  • the present invention has the following gist.
  • the maleic anhydride compound represented by the following formula (1) is photodimerized in a reaction solvent 100 mass times or more with respect to the maleic anhydride compound. , 2,3,4-cyclobutanetetracarboxylic acid-1,2: 3,4-dianhydride (1,3-DACBDA) derivative.
  • R represents an alkyl group having 1 to 20 carbon atoms.
  • 2. The production method according to 1 above, wherein R is a methyl group. 3. 3.
  • a sensitizer consisting of benzophenone, acetophenone, benzaldehyde, benzophenone substituted with an electron withdrawing group, acetophenone substituted with an electron withdrawing group, benzaldehyde substituted with an electron withdrawing group, or anthraquinone
  • 7. The production method according to any one of 1 to 6. 8).
  • the electron withdrawing group is at least one selected from the group consisting of a fluoro group, a chloro group, a bromo group, an iodo group, a nitro group, a cyano group, and a trifluoromethyl group. . 9.
  • the present invention is a mixture of 1,3-DACBDA and 1,2-DACBDA by photodimerization reaction of a specific maleic anhydride compound, but it has a highly symmetrical structure as compared with the conventional method.
  • 1,3-DACBDA which is a useful isomer
  • the increase in the conversion rate of the photodimerization reaction of maleic anhydride compound a production method capable of obtaining 1,3, -DACBDA in high yield is provided.
  • 1,2,3,4-cyclobutanetetracarboxylic acid-1,2 3,4-dianhydride represented by formula (2) by photodimerization reaction of maleic anhydride compound represented by formula (1)
  • the production method of (1,3-DACBDA) is represented by the following reaction scheme.
  • R represents an alkyl group having 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms may be either a linear or branched saturated alkyl group or a linear or branched unsaturated alkyl group. Specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, 1-methyl-n-butyl, 2-methyl- n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, n-hexyl, 1-methyl-n-pentyl, 2-methyl-n-pentyl, 1,1-dimethyl-n- Saturated alkyl groups such as butyl, 1-ethyl-n-butyl, 1,1,2-trimethyl-n-propyl, n-heptyl, n-octyl, n-nonyl, n-decyl
  • maleic anhydride compound represented by the formula (1) examples include citraconic anhydride, 2-ethyl maleic anhydride, 2-isopropyl maleic anhydride, 2-n-butyl maleic anhydride, 2-t-butyl anhydride.
  • citraconic anhydride 2-ethylmaleic anhydride, 2-isopropylmaleic anhydride, 2-n-butylmaleic anhydride, 2-t-butylmaleic anhydride, 2 -N-pentylmaleic anhydride, 2-n-hexylmaleic anhydride, 2-n-heptylmaleic anhydride, 2-n-octylmaleic anhydride, 2-n-nonylmaleic anhydride, 2 -N-decylmaleic anhydride, 2-n-dodecylmaleic anhydride and the like are preferable, citraconic anhydride, 2-ethylmaleic anhydride, 2-isopropylmaleic anhydride, 2-n-butylmaleic anhydride, 2-t-butylmaleic anhydride, 2-n-pentylmaleic anhydride, or 2-n-hexylmaleic anhydride is more preferred.
  • the reaction solvent an organic solvent generally used in a photochemical reaction is used.
  • a solvent that can be employed industrially (1) a carbonyl compound having a high photosensitizing effect, (2) the raw material maleic anhydride compound has high solubility, and the decomposition reaction of the produced CBDA derivative compound is carried out.
  • Low solubility of CBDA derivative compound to suppress (3) High solubility of by-product, CBDA derivative compound can be purified only by washing with the same solvent, (4) Not low boiling point that has danger of flammability
  • the CBDA derivative compound is a compound having a boiling point of about 50 to 150 ° C. so that it does not remain, (5) safe for the environment, (6) stable during the photoreaction, and (7) inexpensive.
  • reaction solvent an organic carboxylic acid ester or anhydride, or a carbonic acid ester is preferred.
  • the ester of the organic carboxylic acid is represented by the formula: R 1 COOR 2 (where R 1 is hydrogen or an alkyl group having 1 to 4 carbon atoms, more preferably 1 or 2 carbon atoms, and R 2 has a carbon number. 1 to 4 and more preferably 1 to 3 alkyl groups).
  • esters of organic carboxylic acids include methyl formate, ethyl formate, n-propyl formate, i-propyl formate, n-butyl formate, i-butyl formate, methyl acetate, ethyl acetate, n-propyl acetate, i-acetate -Propyl, n-butyl acetate, i-butyl acetate, methyl propionate, ethyl propionate, n-propyl propionate, i-propyl propionate, n-butyl propionate, i-butyl propionate.
  • ethylene glycol diformate ethylene glycol diacetate, ethylene glycol dipropionate and the like can be used.
  • anhydride of an organic carboxylic acid the formula: (R 1 CO) 2 O (.
  • R 1 is a preferred embodiment be included as defined above) are preferably those represented by.
  • Preferred examples thereof are propionic anhydride, butyric anhydride, trifluoroacetic anhydride, or acetic anhydride. Of these, acetic anhydride is preferred because 1,3-DACBDA can be obtained at a higher recovery rate.
  • carbonic acid ester a carbonic acid dialkyl ester having 1 to 3 carbon atoms, more preferably 1 or 2, is preferable.
  • Preferred examples include dimethyl carbonate, diethyl carbonate, dipropyl carbonate, or a mixture thereof.
  • reaction solvents are ethyl formate, methyl acetate, ethyl acetate, i-propyl acetate, i-butyl acetate, methyl propionate, ethyl propionate, n-propyl propionate, i-propyl propionate, ethylene glycol di- Formate, ethylene glycol diacetate, dimethyl carbonate, or diethyl carbonate, and the most preferred solvent is ethyl acetate or dimethyl carbonate.
  • Each of the above solvents may be used alone or in combination of two or more. However, when used alone, there is an advantage that the treatment after the reaction is easy.
  • the reaction solvent contains ethyl acetate, dimethyl carbonate, diethyl carbonate, or ethylene glycol diacetate
  • the solubility of the raw material maleic anhydride compound is high
  • the produced 1,3-DACBDA Since the target compound is precipitated as a crystal during the reaction due to low solubility, side reactions such as reverse reaction from DACBDA to maleic anhydride compound and oligomer formation can be suppressed.
  • the amount of the reaction solvent used is important, and by using a very large amount of such a reaction solvent, 1,3-DACBDA in the mixture of 1,3-DACBDA and 1,2-DACBDA to be produced is used. It has been found that the selectivity of increases. That is, the reaction solvent is present in an amount of 100 mass times or more, preferably 100 to 300 mass times, more preferably 150 to 250 mass times with respect to the raw material maleic anhydride compound. The selectivity of 3-DACBDA is increased, and a product having a high content of 1,3-DACBDA can be obtained.
  • the wavelength of light is 200 to 400 nm, more preferably 250 to 350 nm, and particularly preferably 280 to 330 nm.
  • a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a xenon lamp, an electrodeless lamp, a light-emitting diode and the like are preferably used because they give a CBDA derivative compound in a particularly high yield.
  • the light source cooling tube from quartz glass to Pyrex (registered trademark) glass as a photochemical reaction device, coloring polymer adhesion to the light source cooling tube and impurities are reduced, and the yield of the CBDA derivative compound is improved.
  • the reaction temperature is preferably from ⁇ 20 to 80 ° C., more preferably, since a polymer is by-produced when the temperature is high, and the solubility of the maleic anhydride compound decreases and the production efficiency decreases when the temperature is low. -10 to 50 ° C. In particular, at 0 to 20 ° C., the production of by-products is greatly suppressed, and 1,3-DACBDA can be obtained with high selectivity and yield.
  • the reaction time varies depending on the amount of maleic anhydride compound, the type of light source, and the amount of irradiation, but it is carried out until the unreacted maleic anhydride compound reaches 0 to 40%, preferably 0 to 10%. it can. Specifically, the reaction time is usually 1 to 200 hours, preferably 1 to 100 hours, and more preferably 1 to 60 hours. The conversion rate can be easily obtained by analyzing the reaction solution by gas chromatography or the like.
  • reaction time becomes longer, the conversion rate of the maleic anhydride compound increases, and the amount of CBDA derivative compound deposited increases, the produced CBDA derivative compound begins to adhere to the outer wall (reaction liquid side) of the light source cooling tube, and the decomposition reaction The coloration of crystals due to the simultaneous use of light and a decrease in light efficiency (yield per unit of power x time) are observed. Therefore, in order to increase the conversion rate of the maleic anhydride compound, it is not preferable to spend a long time in one batch with a decrease in production efficiency in practice.
  • reaction can be performed by a batch type or a distribution type, a batch type is used preferably.
  • the pressure during the reaction may be normal pressure or increased pressure, preferably normal pressure.
  • the production method of the present invention can also be performed by adding a sensitizer.
  • the sensitizer include benzophenone, acetophenone, benzaldehyde, anthraquinone, benzophenone substituted with an electron withdrawing group, acetophenone substituted with an electron withdrawing group, and benzaldehyde substituted with an electron withdrawing group.
  • Examples of the electron withdrawing group include at least one selected from the group consisting of a fluoro group, a chloro group, a bromo group, an iodo group, a nitro group, a cyano group, and a trifluoromethyl group, such as a fluoro group, a chloro group, A bromo group, a cyano group, a trifluoromethyl group, and the like are preferable.
  • Particularly preferred electron withdrawing groups are fluoro groups or chloro groups.
  • the number of electron withdrawing groups is 1 to 10, preferably 1 to 5, and particularly preferably 1 to 3.
  • substitution position of the electron withdrawing group examples include an ortho position, a meta position, and a para position with respect to the carbonyl group, and an ortho position or a para position is preferable.
  • the electron withdrawing groups may be the same or different.
  • anthraquinone in which a carbonyl group having an electron withdrawing effect is crosslinked at the ortho position may be used.
  • benzophenone and benzophenone substituted with an electron withdrawing group include benzophenone, 2-fluorobenzophenone, 3-fluorobenzophenone, 4-fluorobenzophenone, 2-chlorobenzophenone, 3-chlorobenzophenone, 4-chlorobenzophenone, 2 -Cyanobenzophenone, 3-cyanobenzophenone, 4-cyanobenzophenone, 2-nitrobenzophenone, 3-nitrobenzophenone, 4-nitrobenzophenone, 2,4'-dichlorobenzophenone, 4,4'-difluorobenzophenone, 4,4'- Dichlorobenzophenone, 4,4′-dibromobenzophenone, 3,3′-bis (trifluoromethyl) benzophenone, 3,4′-dinitrobenzophenone, 3,3′-dinitrobenzophenone, , 4'-dinitrobenzophenone, 2-chloro-5-nitrobenzophenone, 1,3-bis (4-fluorobenzoyl)
  • acetophenone and acetophenone substituted with an electron withdrawing group include acetophenone, 2′-fluoroacetophenone, 3′-fluoroacetophenone, 4′-fluoroacetophenone, 2′-chloroacetophenone, 3′-chloroacetophenone, 4 ′ '-Chloroacetophenone, 2'-cyanoacetophenone, 3'-cyanoacetophenone, 4'-cyanoacetophenone, 2'-nitroacetophenone, 3'-nitroacetophenone, 4'-nitroacetophenone, 2', 4'-difluoroacetophenone, 3 ′, 4′-difluoroacetophenone, 2 ′, 4′-dichloroacetophenone, 3 ′, 4′-dichloroacetophenone, 4′-chloro-3′-nitroacetophenone, 4′-bromo-3′-nitroacetophenone, 4 - fluor
  • 4'-fluoroacetophenone, 4'-chloroacetophenone, 2 ', 4'-difluoroacetophenone, 3', 4'-difluoroacetophenone, 2 ', 4'-dichloroacetophenone, or 3', 4'-dichloro Acetophenone is preferred.
  • benzaldehyde substituted with benzaldehyde and an electron withdrawing group examples include benzaldehyde, 2-fluorobenzaldehyde, 3-fluorobenzaldehyde, 4-fluorobenzaldehyde, 2-chlorobenzaldehyde, 3-chlorobenzaldehyde, 4-chlorobenzaldehyde, 2-cyanobenzaldehyde.
  • 4-fluorobenzaldehyde, 4-chlorobenzaldehyde, 2,4-difluorobenzaldehyde, 3,4-difluorobenzaldehyde, 2,4-dichlorobenzaldehyde, or 3,4-dichlorobenzaldehyde is preferable.
  • the amount of the sensitizer to be used is not particularly limited as long as the photoreaction rate is accelerated, but is preferably 0.1 to 20 mol%, more preferably 0.1 to 20 mol% based on the maleic anhydride compound. 5 mol%.
  • the above-mentioned benzophenone derivative, acetophenone derivative, or benzaldehyde derivative may be used alone or in combination of one or more of these, but when used alone, Easy to process.
  • the target compound can be obtained by photoreaction, filtering the precipitate in the reaction solution, washing the filtered product with an organic solvent, and drying under reduced pressure.
  • the amount of the organic solvent used for washing the filtered material may be an amount that can transfer the precipitate remaining in the reaction tank to the filter, but when the amount of the organic solvent is large, the target compound is filtered. The recovery rate decreases.
  • the amount of the organic solvent used for washing the filtered product is preferably 0.5 to 10 times by weight, more preferably 1 to 2 times by weight, based on the maleic anhydride compound used in the reaction.
  • the organic solvent used for washing the filtered product is not particularly limited, but the use of a solvent having a high product solubility is not preferable because the target compound is transferred to the filtrate and the recovery rate is lowered. For this reason, as an organic solvent used for washing the filtered product, there are methyl formate, ethyl formate, n-propyl formate, i-propyl formate, n-butyl formate, and formic acid i, which are reaction solvents used for the photodimerization reaction.
  • ⁇ 1 H NMR analysis conditions Apparatus: Fourier transform type superconducting nuclear magnetic resonance apparatus (FT-NMR) INOVA-400 (manufactured by Varian) 400 MHz, Solvent: DMSO-d6, internal standard substance: tetramethylsilane (TMS).
  • FT-NMR Fourier transform type superconducting nuclear magnetic resonance apparatus
  • Solvent DMSO-d6, internal standard substance: tetramethylsilane (TMS).
  • TMS tetramethylsilane
  • Melting point analysis conditions Equipment: DSC1 (Metler Toledo), Temperature: 35 ° C-5 ° C / min-400 ° C, Pan: Au (sealed).
  • Example 1 Under a nitrogen atmosphere, in a 30 mL Pyrex glass test tube, 0.10 g (0.89 mmol) citraconic anhydride (CA) and 20 g (222 mmol, citraconic anhydride (CA) dimethyl carbonate 200 wt times) was added and dissolved by stirring with a magnetic stirrer. Thereafter, a 100 W high pressure mercury lamp was irradiated for 4 hours while stirring at 10-15 ° C. Thereafter, 2 g of the reaction solution in the reactor was collected, and the solvent was distilled off with an evaporator at 70-80 Torr.
  • CA citraconic anhydride
  • CA citraconic anhydride
  • Examples 2 to 7 and Comparative Examples 1 to 5 A series of operations were carried out in the same manner as in Example 1 using the solvent shown in Table 1 below, whether or not 4,4′-dichlorobenzophenone (DClBP) was added, the amount of citraconic anhydride (CA) charged, and the amount of solvent. It carried out similarly. Further, the production ratio of 1,3-DM-CBDA and 1,2-DM-CBDA (1,3-DM-CBDA: 1,2-DM-CBDA) was calculated in the same manner as in Example 1. The following table shows the solvent, presence / absence of DCIBP addition, CA charge amount, solvent amount, and results.
  • DClBP 4,4′-dichlorobenzophenone
  • CA citraconic anhydride
  • 1,3-DACBDA which is a cyclobutanetetracarboxylic acid derivative obtained in the present invention, is a compound useful as a raw material for polyamic acid, polyimide, and the like.
  • the polyimide and the like are used as protective materials and insulating materials for liquid crystal display elements and semiconductors. It is widely used industrially as a resin composition used for electronic materials.
  • the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2014-007185 filed on January 17, 2014 are incorporated herein as the disclosure of the specification of the present invention. Is.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production, à un haut rendement, d'un dérivé acide cyclobutane tétracarboxylique-1,2:3,4-dianhydride qui est utile comme matière première de polyimide ou analogue. La présente invention concerne un procédé de production d'un acide cyclobutane tétracarboxylique-1,2:3,4-dianhydride représenté par la formule (2) par la photodimérisation d'un composé anhydride maléique représenté par la formule (1) dans un solvant réactionnel de 100 doublements de masse ou plus par rapport au composé anhydride maléique. (1) (2) (Dans la formule, R est un groupe alkyle ayant 1 à 20 atomes de carbone.)
PCT/JP2015/051146 2014-01-17 2015-01-16 Procédé de production de dérivé acide cyclobutane tétracarboxylique WO2015108167A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201580004875.1A CN105916867A (zh) 2014-01-17 2015-01-16 环丁烷四羧酸衍生物的制造方法
KR1020167018451A KR20160108335A (ko) 2014-01-17 2015-01-16 시클로부탄테트라카르복실산 유도체의 제조 방법
KR1020217025078A KR20210100756A (ko) 2014-01-17 2015-01-16 시클로부탄테트라카르복실산 유도체의 제조 방법
KR1020227015850A KR102653978B1 (ko) 2014-01-17 2015-01-16 시클로부탄테트라카르복실산 유도체의 제조 방법
JP2015557901A JP6565686B2 (ja) 2014-01-17 2015-01-16 シクロブタンテトラカルボン酸誘導体の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014007185 2014-01-17
JP2014-007185 2014-01-17

Publications (1)

Publication Number Publication Date
WO2015108167A1 true WO2015108167A1 (fr) 2015-07-23

Family

ID=53543050

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/051146 WO2015108167A1 (fr) 2014-01-17 2015-01-16 Procédé de production de dérivé acide cyclobutane tétracarboxylique

Country Status (5)

Country Link
JP (1) JP6565686B2 (fr)
KR (3) KR102653978B1 (fr)
CN (2) CN105916867A (fr)
TW (1) TWI650304B (fr)
WO (1) WO2015108167A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015108169A1 (fr) * 2014-01-17 2015-07-23 日産化学工業株式会社 Procédé de production d'un dérivé de l'acide cyclobutane tétracarboxylique
JP6565686B2 (ja) * 2014-01-17 2019-08-28 日産化学株式会社 シクロブタンテトラカルボン酸誘導体の製造方法
JP6939263B2 (ja) * 2017-08-29 2021-09-22 Jsr株式会社 シクロブタン誘導体の製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006328027A (ja) * 2005-05-30 2006-12-07 Nof Corp シクロブタンテトラカルボン酸二無水物類の製造方法
JP2006347931A (ja) * 2005-06-15 2006-12-28 Nissan Chem Ind Ltd ジアルキルシクロブタン酸二無水物及びその製造法
WO2008153287A1 (fr) * 2007-06-13 2008-12-18 Korea Research Institute Of Chemical Technology Couches de photoalignement en polyimide alicyclique substitué usinables à faible température et procédé de préparation de cellules à cristaux liquides

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017313A (en) * 1974-09-30 1977-04-12 E. I. Du Pont De Nemours And Company Photosensitive composition containing a leuco dye, a photosensitizer, an aromatic aldehyde and a secondary or tertiary amine and the use thereof in a direct-print process
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
JPS59212495A (ja) * 1983-05-19 1984-12-01 Nissan Chem Ind Ltd １，２，３，４−シクロブタンテトラカルボン酸−１，２「い」３，４−ジ無水物の製造方法
JPS60188427A (ja) 1984-03-09 1985-09-25 Nissan Chem Ind Ltd 新規なポリイミド樹脂及びその製造方法
JPH0224294Y2 (fr) 1984-10-25 1990-07-03
JP2923007B2 (ja) 1990-08-28 1999-07-26 チッソ株式会社 溶媒可溶性ポリイミド、その製造法及びカラーフィルター用材料
JP4852206B2 (ja) * 2001-12-26 2012-01-11 日産化学工業株式会社 シクロブタンテトラカルボン酸二無水物化合物の製造法
TWI279403B (en) * 2004-10-20 2007-04-21 Eternal Chemical Co Ltd Cyclobutanetetracarboxylate compound and preparation method thereof
JP5027556B2 (ja) 2006-07-28 2012-09-19 株式会社カネカ ポリイミド樹脂、及びこれを用いたポリイミド樹脂層、積層体、積層体の製造方法、光学補償部材
JP4928347B2 (ja) 2007-05-09 2012-05-09 株式会社カネカ ポリイミド、ポリイミドワニス、光学補償フィルム及びポリイミド、光学補償フィルムの製造方法。
JP5651953B2 (ja) * 2008-01-25 2015-01-14 日産化学工業株式会社 液晶配向剤、及び液晶表示素子
JP5609651B2 (ja) * 2009-02-12 2014-10-22 日産化学工業株式会社 テトラカルボン酸誘導体、その製造方法、及び液晶配向剤
JP6565686B2 (ja) * 2014-01-17 2019-08-28 日産化学株式会社 シクロブタンテトラカルボン酸誘導体の製造方法
WO2015108166A1 (fr) * 2014-01-17 2015-07-23 日産化学工業株式会社 Procédé de production d'un dérivé de l'acide cyclobutane tétracarboxylique
KR20220162884A (ko) * 2014-01-17 2022-12-08 닛산 가가쿠 가부시키가이샤 시클로부탄테트라카르복실산 유도체의 제조 방법

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006328027A (ja) * 2005-05-30 2006-12-07 Nof Corp シクロブタンテトラカルボン酸二無水物類の製造方法
JP2006347931A (ja) * 2005-06-15 2006-12-28 Nissan Chem Ind Ltd ジアルキルシクロブタン酸二無水物及びその製造法
WO2008153287A1 (fr) * 2007-06-13 2008-12-18 Korea Research Institute Of Chemical Technology Couches de photoalignement en polyimide alicyclique substitué usinables à faible température et procédé de préparation de cellules à cristaux liquides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
POLYMER INTERNATIONAL, vol. 63, no. ISSUE, pages 486 - 500 *

Also Published As

Publication number Publication date
CN105916867A (zh) 2016-08-31
TW201542498A (zh) 2015-11-16
KR20160108335A (ko) 2016-09-19
JP6565686B2 (ja) 2019-08-28
JPWO2015108167A1 (ja) 2017-03-23
KR102653978B1 (ko) 2024-04-02
CN110590798A (zh) 2019-12-20
TWI650304B (zh) 2019-02-11
KR20210100756A (ko) 2021-08-17
KR20220063315A (ko) 2022-05-17

Similar Documents

Publication Publication Date Title
JP7021640B2 (ja) ジオール、ジオールの製造方法、ジ（メタ）アクリレートおよびジ（メタ）アクリレートの製造方法
KR102254089B1 (ko) 시클로부탄테트라카르복실산 유도체의 제조 방법
JP6565687B2 (ja) シクロブタンテトラカルボン酸誘導体の製造方法
JP6565686B2 (ja) シクロブタンテトラカルボン酸誘導体の製造方法
TWI649323B (zh) Method for producing cyclobutane tetracarboxylic acid derivative
JP6919745B2 (ja) 高純度の１，３−ジアルキルシクロブタン−１，２，３，４−テトラカルボン酸−１，２：３，４−二無水物の製造方法
RU2471770C1 (ru) Способ получения низкомолекулярных замещенных фенилбензоатов

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15737787

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2015557901

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 20167018451

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15737787

Country of ref document: EP

Kind code of ref document: A1