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WO1993014148A1 - Compositions a base de resine de polyimide et procedes de production de ces compositions - Google Patents

Compositions a base de resine de polyimide et procedes de production de ces compositions Download PDF

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Publication number
WO1993014148A1
WO1993014148A1 PCT/JP1988/000145 JP8800145W WO9314148A1 WO 1993014148 A1 WO1993014148 A1 WO 1993014148A1 JP 8800145 W JP8800145 W JP 8800145W WO 9314148 A1 WO9314148 A1 WO 9314148A1
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WO
WIPO (PCT)
Prior art keywords
polyimide
organic solvent
bis
resin composition
composition according
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/JP1988/000145
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English (en)
Japanese (ja)
Inventor
Tsuyoshi Ikeda
Mikio Nakazawa
Hiroshi Manami
Yuji Kawashima
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.)
Individual
Original Assignee
Individual
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
Priority claimed from JP17975287A external-priority patent/JPS6422963A/ja
Application filed by Individual filed Critical Individual
Priority to US07/275,176 priority Critical patent/US4996293A/en
Anticipated expiration legal-status Critical
Publication of WO1993014148A1 publication Critical patent/WO1993014148A1/fr
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
    • C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds

Definitions

  • the present invention relates to a novel polyimide resin composition and a method for producing the same.
  • Aromatic polyimides have high heat resistance and good mechanical and electrical properties, but on the other hand, they do not generally melt and are insoluble in ordinary organic solvents, which makes them difficult to mold. have.
  • aromatic tetraimide dianhydride which is a raw material of aromatic polyimide, and aromatic diamine are reacted in a polar organic solvent to obtain a polyamide acid.
  • a method of synthesizing a soluble intermediate such as a compound, giving a shape at this stage, and dehydrating and ring-closing under high temperature to obtain a polyimide is generally performed.
  • the stability of the intermediate is poor, and the viscosity changes or becomes cloudy when left at room temperature. Since the dehydration reaction is performed after molding, defects such as voids and pinholes are likely to occur, and smooth and uniform molding is performed. The disadvantage is that it is difficult to get a body.
  • the m, m 'diamino compound used has a disadvantage that it is extremely difficult to synthesize and has poor reactivity as compared with the P, p' diamino compound generally used as an aromatic diamine component. are doing.
  • a method for producing a soluble polyamide using a P, P 'diamino compound a method using two or more kinds of aromatic tetracarboxylic acid components having different skeleton structures in combination is used.
  • Japanese Patent Application Laid-Open Nos. 61-28526 and 61-51033 Japanese Patent Application Laid-Open Nos. 61-28526 and 61-51033
  • it is difficult to produce the same material because the polymer structure is not uniform.
  • An object of the present invention is to provide a novel organic solvent solution polyimide resin composition and a method for producing the same.
  • Another object of the present invention is to provide a novel polymer which is easy to mold because it is an organic solvent solution after sufficiently exhibiting the inherent properties of aromatic polyimide such as heat resistance, mechanical properties, and electrical properties.
  • Still another object of the present invention is to provide a novel organic solvent solution polyimide resin composition having excellent heat resistance, mechanical properties, electrical properties, etc., and also excellent adhesion to a substrate, It is to provide a manufacturing method.
  • the present invention provides the following polyimide resin composition and a method for producing the same.
  • One C-one, Y is a single bond or one 0-, one S-,
  • R 1 and R 2 may be substituted with a hydrogen atom, a halogen atom or a halogen atom It represents a lower alkyl group, which may be the same or different.
  • a polyimide resin composition characterized by further adding a silane coupling agent to the composition.
  • a method for producing a resin composition Reacting with an aromatic diamine represented by the formula (1) in the presence of an organic solvent to produce a polyimide, or separating the produced polyimide and then re-dissolving it in an organic solvent.
  • a method for producing a resin composition Reacting with an aromatic diamine represented by the formula (1) in the presence of an organic solvent to produce a polyimide, or separating the produced polyimide and then re-dissolving it in an organic solvent.
  • Diphenylsulfone-1,3 ', 4,4'-tetracarboxylic acid dihydrate alone is used as the aromatic tetracarboxylic acid component, and the above is used as the aromatic diamine component.
  • Polyimides obtained using specific p, p 'diamino compounds are soluble in organic solvents and have high intrinsic viscosity (ie, high molecular weight) and high uniformity of polymer structure. Excellent heat resistance, mechanical properties, electrical properties, etc.
  • an aromatic tetracarboxylic acid component other than the above for example, benzophenone-1,3,3,4,4'-tetracarboxylic dianhydride ⁇ pyromellitic dianhydride is used. However, it does not become soluble in organic solvents.
  • the present invention has been completed based on these new findings.
  • the polyimide resin composition of the above A can be produced by the production method of the above C. More specifically, it can be produced as follows.
  • DSTA diphenylsulfone-1,3 ', 4,4'-tetracarboxylic dianhydride
  • DSTA diphenylsulfone-1,3 ', 4,4'-tetracarboxylic dianhydride
  • a p, p'-diamino compound represented by the general formula ( ⁇ ) is used as the aromatic diamine component.
  • Preferred examples are 4,4'-diamino diphenyl sulfide and 2,2-bis [4- (p-amino phenoxy) phenyl] prono III.
  • aromatic diamine component it is most preferable to use one of the above P, P'-diamino compounds alone from the viewpoint of homogeneity of the polymer structure, but if necessary, Terror
  • the production reaction of polyimide is usually carried out by a two-step reaction of a synthesis reaction of polyamic acid, which is an intermediate, and a reaction of dehydrating and cyclizing this to form polyimide.
  • the molar ratio between DSTA and the aromatic diamin is preferably about 0.7 to 1.3 in order to obtain a high molecular weight polyimide, and particularly preferably 0.95 to 1.05. Range is preferred.
  • the reaction temperature is generally about 0 to 120, preferably 5 to 80. C, and the reaction time is usually about 0.5 to 50 hours, depending on the diamines, solvents and other conditions used.
  • organic solvent used in this reaction it is preferable to use a non-proton-based polar solvent or a phenol-based solvent that can dissolve the polyimide to be formed later.
  • organic solvents include, for example, N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylformamide, N, N-dimethylacetamide, N, N—
  • Non-protonic polar solvents such as dimethyl acetate, dimethyl sulfoxide, tetramethyl urea, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoramide;
  • phenol solvents such as phenol, cresol, dimethylphenol, chlorophenol, and bromphenol.
  • the reaction mixture does not gel even if some polyimide is formed in the synthesis of polyamic acid.
  • the polyimide resin composition of the present invention can be directly subjected to an imidization reaction as it is, and can be directly used as the polyimide resin composition of the present invention after the imidization reaction. Very suitable.
  • the polyamic acid is recovered by a conventional method, purified if necessary, then dissolved again in a non-proton polar solvent or a phenol solvent, and the imidization reaction is performed. It is desirable.
  • the organic solvent solution of the polyamic acid obtained in the above polyamic acid synthesis reaction may be used as it is or after recovering boriamic acid from the organic solvent solution by a conventional method, purifying as necessary, and then re-using the above-mentioned non-protic acid. It can be used in an imidization reaction after being dissolved in a ton-based polar solvent or a phenol-based solvent.
  • the organic solvent in the above polyamic acid synthesis reaction and the subsequent imidization reaction may be used alone at any stage, or may be used as a mixture of two or more.
  • the imidization reaction can be suitably performed using a solution of a polyamic acid in a nonproton-based polar solvent or a phenol-based solvent.
  • the reaction temperature is usually about 60 to 250 ° C, preferably 100 to 200 ° C. (: It is not possible to obtain an economical reaction rate below 60 ° C, and at 250 ° C or higher. In such a case, coloring of the reaction system and side reactions are disadvantageous.
  • a solvent azeotropic with water and Z or a dehydrating agent may be added.
  • solvents include benzene, toluene, xylene, ethylbenzene, hexane, heptane, octane, nonane, decane, cyclohexane and the like, and dehydrating agents such as pentoxide, acetic anhydride, pyridine and acetic anhydride.
  • Etc. are exemplified.
  • the reaction time of the imidization reaction varies depending on various conditions such as the type of polyamic acid and the solvent, but is usually about 0.5 to 50 hours. Further, the concentration of the polyamic acid in the reaction solution is usually about 1 to 50% by weight, and particularly preferably 3 to 40% by weight. If it is less than 1% by weight, it is economically disadvantageous, and if it exceeds 50% by weight, the reaction solution is not preferred because it gels or the viscosity becomes too high and the reaction becomes uneven.
  • the polyimide in the present invention has a high solubility in an organic solvent by using the specific aromatic tetracarboxylic acid component and the aromatic diamine component in a selective combination.
  • a polyimide having a sufficiently large intrinsic viscosity that is, a sufficiently large molecular weight
  • the polymer in the present invention Do intrinsic viscosity? ? inh is 0.5 gZ1002 in solvent N-methyl-2-pyrrolidone, temperature 30 ⁇ 1. C, which is usually between 0.3 and
  • the polyimide resin composition of the present invention is obtained by dissolving the above polyimide in an organic solvent.
  • the organic solvent it is particularly preferable to use at least one of the non-proton-based polar solvent and the phenol-based solvent mentioned in the polyimide formation reaction, from the viewpoints of solubility, stability of solution viscosity and the like.
  • the composition of the present invention can be used as it is as a reaction product.
  • a non-proton-based polar solvent is used.
  • the composition of the present invention can be re-dissolved in a funinol solvent or the like.
  • the concentration of the polyimide in the polyimide resin composition of the present invention is usually about 1 to 50% by weight, preferably 3 to 40% by weight. Good to do. If it is less than 1% by weight, it is economically disadvantageous, and if it exceeds 50% by weight, the composition gels or the viscosity becomes too high and the workability at the time of molding is unfavorably reduced.
  • the polyimide resin composition of the present invention can be obtained by further adding a silane coupling agent to the polyimide resin composition of the present invention.
  • the above composition has excellent adhesion to a substrate without deteriorating heat resistance, mechanical properties, electrical properties, etc. of polyimide by adding a silane coupling agent. It is.
  • the properties of polyimide are not impaired because the silane coupling agent is added after the imidization is completed, so that it is not incorporated into the polyimide molecular chain and is not affected by the generated water. it is conceivable that.
  • silane coupling agent to be added examples include, for example, ⁇ -glycidoxypropyl trimethoxysilane, ⁇ - (2-aminoethyl) aminoprovir trimethoxysilane, and ⁇ - (2-amidoethyl).
  • composition obtained by dissolving the polyimide of the present invention and the composition obtained by further adding a silane coupling agent are relatively low-viscosity solutions that are fluid at room temperature, and therefore, are difficult to handle and process. Extremely easy. In addition, it is highly stable in solution, and can be stored at room temperature for a long period of time without causing changes such as viscosity changes and precipitation of insolubles.
  • These compositions of the present invention can be suitably used for, for example, heat-resistant varnishes, heat-resistant laminates, heat-resistant films, heat-resistant adhesives, and the like, electrical materials, electronic materials, and applied devices thereof.
  • a printed wiring board a flexible wiring board, a tape carrier, a surface protective film or an interlayer insulating film of a semiconductor integrated circuit element, a covering material for an enameled electric wire, various laminated board gaskets, and the like.
  • these compositions of the present invention are suitable for film use.
  • the composition is relatively heated and the like.
  • Organic solvents and the like can be removed at a low temperature, so that a transparent polyimide film can be easily obtained.
  • This film has high mechanical strength and high flexibility.
  • a film with a thickness of 30 zm can sufficiently withstand repeated bending tests.
  • the thermal decomposition temperature is 50,000 or more, good heat resistance is exhibited, and chemical resistance is also good.
  • the melting temperature it shows thermoplasticity and can be thermocompression-bonded or compressed.
  • the composition of the present invention to which a silane coupling agent has been added can be used for various substrates, for example, metals such as glass, silicon, aluminum, copper, nickel, and iron, and oxides thereof, polyethylene, Polypropylene, Polyethylene terephthalate Good for application to plastics such as rates.
  • the composition is extremely excellent in adhesiveness to the substrate, so that the polyimide film can be formed in a short time at a low temperature only by evaporating the solvent, and the substrate is heated to a high temperature.
  • it is extremely advantageous for applications such as a semiconductor surface protective film, an insulating protective film for electronic component circuits, and an alignment film for a liquid crystal display element used as a plastic substrate.
  • the polyimide solution thus obtained was poured into methanol, the polymer obtained by reprecipitation was dried under reduced pressure, and the infrared absorption spectrum was measured.
  • Table 2 shows the intrinsic viscosity, thermal decomposition temperature, softening point and other physical properties of the polyimide.
  • this polyimide is composed of N, N-dimethylformamide (hereinafter referred to as "DMF"), N, N-dimethylacetamide, dimethylsulfoxide, tetramethylurine, 1, 3—Dimethyl-2-imidazolidinone, m—Cresol, xylenore, 0—Curofen phenol, and p—Bromophenol
  • Table 2 shows the intrinsic viscosity, thermal decomposition temperature, softening point and other physical properties of the polyimide.
  • the polyimide also dissolves in NMP, dimethyl acetate, dimethyl sulfoxide, hexamethylphosphoramide, phenol, o-cresol, 2,6-xylenol, and P-chlorophenol. Then, a polyimide resin solution having a concentration of 10% by weight was obtained.
  • Table 2 shows the intrinsic viscosity, thermal decomposition temperature, softening point and other physical properties of the polyimide.
  • this polyimide readily dissolves in NMP, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, tetramethylurea, phenol, and xylenol.
  • a polyimide resin solution having a concentration of about 10% by weight was obtained. Examples 4 to 11
  • Table 3 shows the intrinsic viscosity (77 inh) of the polyimide obtained, the reaction solvent used, the viscosity of the polyimide solution after the reaction, and the thermal decomposition temperature.
  • the cellotape peel test (the number peeled out of 100 pieces) was 0.
  • the pyrolysis temperature was 558.
  • the cellotape peel test was 60.
  • Example 39 A polyimide varnish was obtained by dissolving 5 g of the polyimide obtained in Example 3 and 0.4 g of amercaptopropyl trimethoxysilane in 50 g of NMP. The adhesion test and the thermal decomposition temperature were measured in the same manner as in Example 37, and the results are shown in Table 4.
  • Example 40
  • Example 12- Each polyimid obtained in 25, 32-35 Polyimide varnish was prepared by dissolving 5% by weight of 7-glycidoxyprobitrimethoxysilane in various non-protonic polar solvents. Table 6 shows the solvent used, the polyimide concentration, the adhesion test measured in the same manner as in Example 37, and the thermal decomposition temperature.
  • the properties of the polyimide obtained are: intrinsic viscosity 0.15 d ⁇ ⁇ Zg, thermal decomposition temperature 420, tensile strength 32 kg / in in 2 , low intrinsic viscosity (low molecular weight ), Heat resistance and mechanical properties were inferior.
  • the adhesion test and the thermal decomposition temperature were measured in the same manner as in Example 37, using a phenol obtained by adding 1.lg of glycidoxyprovirt rimethoxysilane to 100 g of this polyamic acid solution. did. As a result, since the strength of the coating film was very low and not uniform, it was detached when the coating film was cut. The thermal decomposition temperature was as low as 483.
  • FIG. 1 is an infrared absorption spectrum of polyimide in Example 1.

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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)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Compositions de résine de polyimide (A) et (B) et procédés de production de ces compositions. La composition A comprend une solution dans un solvant organique d'au moins un polyimide comportant des unités répétitives représentées par la formule générale (I) dans laquelle Z représente -S-, (a), (b) ou (c), où X représente -O-, -S-, ou (d), et Y représente une simple liaison ou un groupe divalent sélectionné parmi -O-, -S-, -SO2-, (e) et -CO-, et R1 et R2, qui peuvent être identiques ou différents, représentent chacun un atome d'hydrogène, un atome d'halogène ou un groupe alkyle inférieur éventuellement substitué par un halogène et possédant une viscosité intrinsèque comprise entre environ 0,3 et 5,0 dl/g. La composition B est préparée par l'addition d'un agent copulant à base de silane à la composition de résine A.
PCT/JP1988/000145 1987-02-13 1988-02-12 Compositions a base de resine de polyimide et procedes de production de ces compositions Ceased WO1993014148A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US07/275,176 US4996293A (en) 1987-02-13 1988-02-12 Composition comprising polyimide resin from diphenyl sulfone -3,3',4,4'-tetracarboxylic acid dianhydride

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP3203087 1987-02-13
JP62/32030 1987-02-13
JP62/179752 1987-07-17
JP17975287A JPS6422963A (en) 1987-07-17 1987-07-17 Polyimide resin composition and production thereof

Publications (1)

Publication Number Publication Date
WO1993014148A1 true WO1993014148A1 (fr) 1993-07-22

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5230319B2 (fr) * 1974-06-28 1977-08-06
JPS6128526A (ja) * 1984-07-20 1986-02-08 Japan Synthetic Rubber Co Ltd 有機溶媒可溶性ポリイミド化合物の製法
JPS6151033A (ja) * 1984-08-18 1986-03-13 Japan Synthetic Rubber Co Ltd 有機溶媒可溶性ポリイミド化合物の製法
JPS6183229A (ja) * 1984-09-29 1986-04-26 Nitto Electric Ind Co Ltd ポリイミド膜形成用樹脂液の製法
JPS61123634A (ja) * 1984-11-19 1986-06-11 Japan Synthetic Rubber Co Ltd 有機溶媒可溶性ポリイミド化合物の製法
JPS6218426A (ja) * 1985-04-26 1987-01-27 イ−・アイ・デユポン・ドウ・ヌム−ル・アンド・カンパニ− ポリイミド組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5230319B2 (fr) * 1974-06-28 1977-08-06
JPS6128526A (ja) * 1984-07-20 1986-02-08 Japan Synthetic Rubber Co Ltd 有機溶媒可溶性ポリイミド化合物の製法
JPS6151033A (ja) * 1984-08-18 1986-03-13 Japan Synthetic Rubber Co Ltd 有機溶媒可溶性ポリイミド化合物の製法
JPS6183229A (ja) * 1984-09-29 1986-04-26 Nitto Electric Ind Co Ltd ポリイミド膜形成用樹脂液の製法
JPS61123634A (ja) * 1984-11-19 1986-06-11 Japan Synthetic Rubber Co Ltd 有機溶媒可溶性ポリイミド化合物の製法
JPS6218426A (ja) * 1985-04-26 1987-01-27 イ−・アイ・デユポン・ドウ・ヌム−ル・アンド・カンパニ− ポリイミド組成物

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