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WO1998010009A1 - Procede pour preparer une resine de phenol polyhydrique a teneur en polyimide, composition de resine epoxyde comprenant cette resine et produit vulcanise a base de cette composition - Google Patents

Procede pour preparer une resine de phenol polyhydrique a teneur en polyimide, composition de resine epoxyde comprenant cette resine et produit vulcanise a base de cette composition Download PDF

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Publication number
WO1998010009A1
WO1998010009A1 PCT/JP1997/003138 JP9703138W WO9810009A1 WO 1998010009 A1 WO1998010009 A1 WO 1998010009A1 JP 9703138 W JP9703138 W JP 9703138W WO 9810009 A1 WO9810009 A1 WO 9810009A1
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WO
WIPO (PCT)
Prior art keywords
polyimide
resin
epoxy resin
phenolic resin
phenolic
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP1997/003138
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English (en)
Japanese (ja)
Inventor
Masashi Kaji
Yukihiro Wada
Kazuhiko Inoue
Kiyokazu Yonekura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Steel Chemical and Materials Co Ltd
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Nippon Steel Chemical Co Ltd
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 Nippon Steel Chemical Co Ltd filed Critical Nippon Steel Chemical Co Ltd
Publication of WO1998010009A1 publication Critical patent/WO1998010009A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to a polyimide-containing polyvalent phenolic resin having excellent heat resistance, high toughness, and high adhesiveness, and useful as a curing agent for epoxy resins.
  • the present invention also relates to a method for producing the same, and an epoxy resin composition and a cured product thereof.
  • curing agents for epoxy resin compositions used in the fields of powder coatings, semiconductor encapsulating materials and the like include phenol novolacs, phenols and phenols.
  • Lanolekyl resin is widely used.
  • the resulting cured product is generally brittle, and has problems in adhesion to various substrates, adhesiveness, and the like.
  • a method of adding one component of rubber or elastomer is being studied (
  • polyimide As a method for solving the above problem, it is conceivable to combine with a polyimide having excellent thermal and mechanical properties.
  • polyimide is an organic polymer compound having high heat resistance and good electric and mechanical properties, it is a protective material and an insulating material in the field of electronic devices. They are widely used as adhesives, films, and structural materials.
  • Polyimide generally has a high melting point or high glass transition point In many cases, the temperature exceeds or is close to the thermal decomposition temperature, making it difficult to perform melt molding.In addition, the method of melting and mixing is used for the same reason. It has also been difficult to form a composite with other materials such as epoxy resin.
  • Japanese Patent Application Laid-Open No. Sho 61-250301 discloses a special pillomerite imid. Copolymer as a fusible polyimid copolymer. Proposed .
  • the melting point of the copolymer is in the range of 140 to 210 ° C. as far as the embodiment is concerned.
  • the copolymer in order to form a phenol, the copolymer is melt-pressed at 400 ° C. I have to heat it to C. Therefore, even with these materials, it has still been difficult to form a composite with other materials such as epoxy resin by a method such as melt mixing. .
  • an object of the present invention is to exhibit excellent properties such as heat resistance, high toughness, and high adhesion without reducing the glass transition point and mechanical strength of the cured product.
  • An object of the present invention is to provide a method for producing a polyimide-containing polyvalent phenolic resin which is particularly useful as a curing agent for epoxy resins.
  • polyimide has a high melting point and is difficult to compound with other materials such as epoxy resin.
  • Polyimides are polymerized in polyhydric phenolic resins, which are common curing agents for xylene resins, resulting in a polymer formed by polymerization.
  • the present inventors have found that the imide is uniformly melted or dispersed in the polyhydric fluorinated resin, and have led to the present invention.
  • the present invention provides a method for reacting an acid anhydride with a diamine compound in the presence of a polyvalent phenolic resin containing two or more phenolic hydroxyl groups in one molecule.
  • the present invention provides a method for producing a polyimide-containing polyvalent phenolic resin, which comprises performing an imidization reaction while performing a dehydration reaction.
  • the present invention uses the above-mentioned polyimide-containing polyvalent phenolic resin as a part or the whole of a curing agent component for an epoxy resin.
  • the present invention is a cured epoxy resin obtained by curing the epoxy resin composition.
  • the polyimide-containing polyfunctional phenolic resin of the present invention is obtained by reacting an acid anhydride with a diammine compound in the presence of a polyhydric phenolic resin, and dehydrating the polyanhydride. It can be obtained by performing an imidization reaction while performing the reaction. At this time, the polyvalent phenolic resin to be used only needs to contain two or more phenolic hydroxyl groups in one molecule.
  • the polyimide-containing polyvalent phenolic resin of the present invention is used as an epoxy resin curing agent, the use of a novolak resin as a synthetic raw material can A cured product having excellent moldability and heat resistance can be obtained, and when an alkyl resin is used, a cured product having particularly excellent moisture resistance can be obtained.
  • the softening point of these polyhydric phenolic resins is not particularly limited, but is usually in the range of 40 ° C. to 150 ° C.
  • the alkyl resin is represented by the following general formula (1), and is an alkyl-substituted or unsubstituted benzene ring or naphtha. It can be obtained by reacting a phenolic hydroxyl group-containing compound having a ren ring with an aromatic crosslinking agent ⁇ ) o
  • A represents an alkyl-substituted or unsubstituted benzene ring or naphthalene ring, and when two or more are contained in one molecule, they may be the same or different.
  • R 1 IV 2 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and p represents 1 or
  • An integer of 2 and m represents a number from 0 to 15)
  • phenolic hydroxyl group-containing compound examples include phenol, 0-cresol, m-cresol, p-cresol, and ethylphenol. Noles, 2,4-xylene, 2,5—xylene, 2,6-xyleno-norre, isopropynolefenols, Benzene ring-containing compounds such as monobutyl phenol, phenyl phenol, phenol, resorcinol, and hydroquinone; Examples thereof include naphtholene ring-containing compounds such as 1-naphthol, 2-naphthol, and naphthalene diols.
  • the aromatic cross-linking agent is 0-body, m-body, p It can be any of the bodies, but is preferably an m-body or a p-body.
  • Examples include (2-pronil) benzene and 1,4-di (2-pronil) benzene.
  • the molar ratio of the two is determined by the phenolic hydroxyl group-containing compound.
  • the aromatic cross-linking agent is not more than 1 mol per 1 mol of the compound, preferably in the range of 0.1 to 0.9 mol. If the amount of the aromatic cross-linking agent is less than 0.1 mol, the amount of the unreacted phenolic hydroxyl group-containing compound becomes large, which is not industrially desirable and exceeds 0.9 mol. If this occurs, the softening point of the resin will increase, which will hinder molding workability.
  • the preferred softening point of the aralkyl-type polyvalent phenolic compound used in the present invention is from 40 to 150 ° C, more preferably from 50 to 1 ° C. 20 ° C. If it is lower than this, there is a problem of blocking during storage, and if it is higher than this, there is a problem in kneadability and moldability in preparing the epoxy resin composition. Also, the preferred melt viscosity at 150 ° C is less than or equal to 20 centimeters voice, and more preferably less than or equal to 5 centimeters voice. . If it is higher than this, there are problems in kneadability and moldability during the preparation of the epoxy resin composition.
  • Preferable examples of the aranoleky type polyvalent phenolic compound used in the present invention include phenol or naphthol, and p-xylile.
  • Polyvinyl alcohol or ⁇ , a'-dimethyxoxy P-quinlene-derived phenolic resin and naphtha larkyl Available from Mitsui Toatsu Chemicals, Inc., Millex XL-225-3L, XL-225-LL, XL—225-M Meiwa Kasei Co., Ltd. MEH-7800, New Japan Examples include SN-180 manufactured by Tekko Chemical Co., Ltd.
  • the acid anhydride used for obtaining the polyimide-containing polyhydric resin containing polyimide of the present invention it is used for synthesizing ordinary polyimide. Use most tetracarboxylic oleic anhydride be able to .
  • the acid anhydride is used to block the terminal group of the polyimide, and is used for phthalic anhydride, 4-chlorophthalic anhydride, and anhydrous tetraethyl anhydride. It is also possible to use dicarboxylic anhydrides such as phthalanol anhydride, 4-hydroxyphthalic anhydride, naphthalic anhydride, and maleic anhydride. .
  • diamine component aromatic diamines, polycyclic diamines, aliphatic diamines, diaminopolysiloxanes Etc. are selected.
  • the aromatic diamines include, for example, diamines such as 0-, m- and p-phenylamine, 2,4-diaminotorenene and the like.
  • Toluenes, 1,4-diaminino-2-methoxybenzen, 2,5-diaminoxylens, 1,3-diaminino-4 _______________________________________ either, chloronobenzen, 1,4-diamino-1,2,5-diamine, 1,3-diamino 4-disopropynolebenzen, ⁇ , ⁇ '-diphenyl 1, 4-diphenylamine, 4, 4 '— Diamino diphenyl 1, 2,2 -pun, 4,4'-diamino diphenyl methane, 2,2 '-diaminotinole , 4,4'-Jaminostinolene, 4,4'-Jamino diphenyl ether, 3,4'-Ja Noji pheny
  • heterocyclic diamines examples include 2,6-diaminopyridin, 2,4-diaminopyridin, and 2,4-diamine. Minnow
  • aliphatic diamine examples include dimethylmethylamine, trimethylenediamine, tetramethylenediamine, and hexadiamine.
  • diaminopolysiloxanes include, for example, the following.
  • 1 represents the number of repeated siloxane bonds.
  • the diamines such as the aromatic diamines, heterocyclic diamines, aliphatic diamines, and diaminopolysiloxanes are one kind.
  • aromatic diamines are particularly preferred from the viewpoint of improving the heat resistance of the obtained polyimide. Is preferred.
  • 2,2-bis [4- (4-aminophenol) is used.
  • bis (3-aminopropyl) polymethylsiloxane are preferred.
  • the molar ratio between tetracarboxylic anhydride and the diammine compound should be adjusted appropriately according to the purpose of use of the polyimide-containing polyvalent phenolic resin. I can do it.
  • Tetracarboxylic anhydride Z diamin The molar ratio of the compound is 0.8 to 1.2 when the heat resistance and the mechanical strength are emphasized, and 0 when the blend property with the epoxy resin and the melt mixing property are emphasized. When the moldability (particularly fluidity) of the epoxy resin composition is taken into account, the value is set to 1.2 to 5.0, and the low-molecular-weight polymer is used. It can also be used as an imido compound.
  • the polyimide-containing polyhydric resin of the present invention reacts an acid anhydride with a diammine compound in the presence of a polyhydric phenolic resin.
  • the respective charging ratios in the reaction are not particularly limited, but are usually 100 parts by weight of the polyhydric phenolic resin.
  • the total amount of the acid anhydride compound and the diamine compound is 5 to 200 parts by weight based on the total weight. If the amount is less than the above, the effect of improving the physical properties by the polyimide when the epoxy resin cured product is small is small. Large increase in viscosity makes handling difficult at the time of synthesis.
  • the reaction is carried out by simultaneously adding tetracarboxylic anhydride and the diamine compound.
  • a specific diamine compound may be added to the total amount of tetracarboxylic anhydride to react first, and then the remaining diamine compound may be added. May be further added and reacted.
  • a part of tetracarboxylic acid anhydride is added to the whole amount of the diamin compound and reacted first, and then the remaining tetracarboxylic acid anhydride is reacted.
  • the reaction may be performed by adding a substance.
  • the imidization reaction is carried out while being dehydrated by heating under stirring. It is done.
  • the reaction temperature is usually from 100 to 300 ° C. If it is lower than this, the reaction time is prolonged, and if it is higher than this, a decomposition reaction of the polyvalent phenolic resin as a reaction medium occurs.
  • the reaction time is generally in the range of 1 to 40 hours. .
  • a solvent may be used for the imidization reaction.
  • the solvent include N-methyl-2-pyrrolidone, N, N-dimethylaminoacetate, N, N-dimethylaminoacetone , Dimethyl alcohol, tetramethyl urea, pyridin, dimethyl alcohol, hexamethyl alcohol, amide, methyl Norehonorumamido, N-acetinore 2-pyrrolidone, ethylene glycol ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Diethylene glycol, methyl ether, cyclone, non-exhaust ⁇ , , ⁇ - ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ,, ⁇ , ⁇ -, ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ 2 1-pyrrolidone, ⁇
  • an aromatic solvent such as benzene, toluene, or quinrene may be used as an azeotropic solvent for prompt dehydration. Further, the reaction may be carried out under reduced pressure for quick dehydration.
  • the epoxy resin is suitable as a curing agent for the epoxy resin, and by combining this with the epoxy resin, the epoxy resin composition can be obtained. it can .
  • the epoxy resin used in this case is not particularly limited.
  • Novolaks obtained by condensation with aldehydes such as honolemaldehyde, acetonolelide, benzolide, etc.
  • Polyglycidyl ethers of polyvalent phenolic compounds such as aralkyl resins such as phenols, phenols, cresols, naphthones, etc.
  • Glysyl ether compounds derived from halogenated bisphenols such as tetrabromobisphenol A and the like. can give .
  • These epoxy resins may be used alone or in combination of two or more.o
  • the epoxy resin composition of the present invention may contain an inorganic filler.
  • the epoxy resin to be used is selected from epoxy resins having excellent low viscosity. 3 ' , 5,5'-Tetramethylen -4,4'-Dihydrogen diphenylene, 3,3 ', 5,5'-Tetramethylen- 4,4'-dihydroxybiphenyl, 2,5-dihydroquinone dihydroquinone, 1,4-vis (3-methyl 1-Hydroxyminole) Benzene, 3,3 ', 5,5, -Tetramethylen-4,4, -Dihydroxy diphenyl Noresure feed, 3, 3'-di-no-shear-buti-noise-5, 5'-dimetho-noise-4, 4'-dihydroxy Feed, 4,4, -dihydroxy phenyl ether, 1,6-naphthene,
  • the inorganic filler examples include molten silica, crystalline silica, aluminum, magnesium, titanium oxide, calcium carbonate, and glass. Fiber, talc, etc. Among them, molten silica is preferably used from the viewpoint of low thermal expansion and the like.
  • the shape of the molten silica may be crushed or spherical, but from the viewpoint of improving the solder heat resistance, the crushed silica having an average particle size of 15 ⁇ m or less and an average particle size of 40
  • a spherical silica having an average particle diameter of 2 // m or less and a spherical silica having an average particle diameter of 2 // m or less are appropriately combined and used.
  • the content of the inorganic filler is usually 30 to 95% by weight, but when used for a semiconductor sealing material, it is preferable from the viewpoint of improving solder heat resistance. Ranges from 65 to 95% by weight.
  • a known curing agent may be mixed and used.
  • the curing agent to be mixed and used any of those generally known as curing agents for epoxy resins can be used.
  • acid anhydrides, amines and the like can be used.
  • the amount of the polyimide It is preferable to use 10% by weight or more of the multifunctional phenolic resin in the total hardener.
  • the epoxy resin composition of the present invention usually contains a curing accelerator.
  • a curing accelerator any conventionally known curing accelerators can be used. For example, any conventionally known curing accelerators can be used.
  • Amins such as, 1,8-diaza-bicyclo (5,4,0) ⁇ decen-7, 2-pentene Nole 4-iminoazoles such as methyl imidazole, organic phosphines such as triphenyl phosphine, and zoleic acid And so on.
  • These curing accelerators are used as a mixture of two or more as necessary. Usually, the amount of the curing accelerator used is 0.1 to 10 parts by weight based on 100 parts by weight of the epoxy resin.
  • the epoxy resin composition of the present invention may further contain a coupling agent, a wax, a flame retardant, a low-stressing agent, a cosmetic, a release agent, and a lubricant. You may mix such as.
  • a polyester, a polyamide, a polyimid, a polyether, a polyether, or the like may be used.
  • Oligomers or high molecular compounds such as urethane, petroleum resin, indicone malon resin, and phenolic resin may be appropriately compounded.
  • the imidization reaction is carried out in the presence of a polyvalent phenol, the phenol resin and the polyimide resin are uniformly mixed. ⁇ Knoll resin is obtained.
  • the hydroxyl group of the phenol resin reacts with the acid anhydride to form an ester bond, but such a case is assumed. Even if the reaction occurs, there is no decrease in the physical properties, and it is considered that effects such as improvement in solubility are produced.
  • FIG. 1 is a drawing showing an infrared absorption spectrum of the polyimide-containing polyvalent phenolic resin A of Example 1.
  • FIG. 2 is a drawing showing an infrared absorption spectrum of the polyimide-containing polyvalent phenolic resin D of Example 4.
  • Example 3 [Production of Polyimide-Containing Polyhydric Resin C]
  • Phenol rubber with a softening point of 75 ° C and a hydroxyl equivalent of 104 is added to a glass slab made of glass with a stiffness of 4 liters.
  • g, pyromellitic acid 47.6 g, high molecular weight 7500 bis (3-amino propylinole) polymethinolexyloxane 163.8 g and mixed xylen (470 g) were charged and reacted in the same manner as in Example 1 to obtain a polyimid-containing polyvalent phenolic resin D61.8.8 g. .
  • the obtained polyimide-containing polyvalent phenolic resin D had a soft point of 87.5 ° C, and was measured with an ICI component viscometer. The melt viscosity at 150 ° C was 0.9 voice.
  • Figure 2 shows the infrared absorption spectrum.
  • Example 5 [Production of Polyimide-Containing Polyhydric Resin E]
  • a softening point is applied to a 2-liter glass separate flask.
  • epoxy resin components bisphenol A-type epoxy resin (epicot 828 oiled shell: epoxy resin X) and softening point 7 1.
  • C 0-cresole novolac type epoxy resin (epoxy resin Y) having an epoxy equivalent of 197 was used, and Examples 1 to 6 were used as curing agents.
  • hardening agent M phenol-norenohol
  • triphenylphosphine as a 3 ⁇ 4- ⁇ -promoting accelerator, these were kneaded in the composition shown in Table 1 to prepare an epoxy resin composition.
  • the polyimide-containing polyvalent phenolic resin of the present invention is used as an epoxy resin curing agent, the glass transition point and mechanical strength of the cured product are reduced.
  • High performance such as heat resistance, high toughness, and high adhesiveness, molding materials and laminated materials It is suitably used as a base resin for various uses such as coating materials.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

Cette invention se rapporte à un procédé pour préparer une résine de phénol polyhydrique à teneur en polyimide, qui consiste à faire réagir un anhydride acide avec un composé de diamine en présence d'une résine de phénol polyhydrique contenant au moins deux groupes hydroxyle phénoliques par molécule, afin de provoquer une réaction d'imidation tout en effectuant une réaction de déshydratation; à une résine de phénol polyhydrique à teneur en polyimide, préparée par ce procédé; à une composition de résine époxyde contenant cette résine de phénol polyhydrique à teneur en polyimide, qui constitue une partie ou la totalité d'un composant d'agent de vulcanisation pour une résine époxyde; et à un produit vulcanisé à base de cette composition. On peut produire un agent de vulcanisation pour une résine époxyde ayant une excellente résistance thermique, une ténacité élevée, un pouvoir d'adhésion élevé et d'autres propriétés excellentes, sans abaisser la température de transition vitreuse et la résistance mécanique du produit ainsi volcanisé.
PCT/JP1997/003138 1996-09-05 1997-09-05 Procede pour preparer une resine de phenol polyhydrique a teneur en polyimide, composition de resine epoxyde comprenant cette resine et produit vulcanise a base de cette composition Ceased WO1998010009A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/235560 1996-09-05
JP23556096A JPH1081748A (ja) 1996-09-05 1996-09-05 ポリイミド含有多価フェノール性樹脂の製造方法並びにそのエポキシ樹脂組成物及びその硬化物

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CN114213629A (zh) * 2021-11-04 2022-03-22 道生天合材料科技(上海)股份有限公司 固化剂、固化剂组合物及其制备方法
CN114806083A (zh) * 2022-06-10 2022-07-29 大同共聚(西安)科技有限公司 一种聚酰亚胺/环氧树脂模塑料及其制备方法
CN115141331A (zh) * 2021-03-29 2022-10-04 长春人造树脂厂股份有限公司 多元酚树脂、多元酚树脂的缩水甘油醚及其应用

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WO2007046405A1 (fr) * 2005-10-21 2007-04-26 Nippon Kayaku Kabushiki Kaisha Composition de resine thermodurcissable et son utilisation
US8410620B2 (en) 2007-09-20 2013-04-02 Nippon Kayaku Kabushiki Kaisha Primer resin for semiconductor device and semiconductor device
JP5439818B2 (ja) * 2009-01-07 2014-03-12 日立化成株式会社 接着剤組成物、フィルム状接着剤、接着シート及び半導体装置
CN108779389A (zh) 2016-01-28 2018-11-09 瓦克化学股份公司 改性的反应型树脂组合物及其用于涂覆支撑剂的用途

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JPS6119633A (ja) * 1984-07-06 1986-01-28 Nitto Electric Ind Co Ltd イミド系化合物またはその前駆体の合成方法
JPS6386746A (ja) * 1986-09-30 1988-04-18 Japan Synthetic Rubber Co Ltd 未架橋ノボラツク樹脂組成物の製造方法
JPS63128024A (ja) * 1986-11-18 1988-05-31 Japan Synthetic Rubber Co Ltd ポリイミド含有未架橋ノボラツク樹脂組成物の製造方法
JPH02242825A (ja) * 1989-03-15 1990-09-27 Nitto Denko Corp イミド系化合物またはその前駆体の製造方法

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Publication number Priority date Publication date Assignee Title
JPS6119633A (ja) * 1984-07-06 1986-01-28 Nitto Electric Ind Co Ltd イミド系化合物またはその前駆体の合成方法
JPS6386746A (ja) * 1986-09-30 1988-04-18 Japan Synthetic Rubber Co Ltd 未架橋ノボラツク樹脂組成物の製造方法
JPS63128024A (ja) * 1986-11-18 1988-05-31 Japan Synthetic Rubber Co Ltd ポリイミド含有未架橋ノボラツク樹脂組成物の製造方法
JPH02242825A (ja) * 1989-03-15 1990-09-27 Nitto Denko Corp イミド系化合物またはその前駆体の製造方法

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115141331A (zh) * 2021-03-29 2022-10-04 长春人造树脂厂股份有限公司 多元酚树脂、多元酚树脂的缩水甘油醚及其应用
CN115141331B (zh) * 2021-03-29 2023-09-15 长春人造树脂厂股份有限公司 多元酚树脂、多元酚树脂的缩水甘油醚及其应用
CN114213629A (zh) * 2021-11-04 2022-03-22 道生天合材料科技(上海)股份有限公司 固化剂、固化剂组合物及其制备方法
WO2023077910A1 (fr) * 2021-11-04 2023-05-11 道生天合材料科技(上海)股份有限公司 Agent de durcissement, composition d'agent de durcissement et procédé de préparation associé
CN114806083A (zh) * 2022-06-10 2022-07-29 大同共聚(西安)科技有限公司 一种聚酰亚胺/环氧树脂模塑料及其制备方法

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