WO2004035689A1 - ピロメリット酸ジ無水物を含むブロック共重合ポリイミド溶液組成物及びその製造方法 - Google Patents
ピロメリット酸ジ無水物を含むブロック共重合ポリイミド溶液組成物及びその製造方法 Download PDFInfo
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- WO2004035689A1 WO2004035689A1 PCT/JP2003/002343 JP0302343W WO2004035689A1 WO 2004035689 A1 WO2004035689 A1 WO 2004035689A1 JP 0302343 W JP0302343 W JP 0302343W WO 2004035689 A1 WO2004035689 A1 WO 2004035689A1
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- dianhydride
- aromatic diamine
- bis
- polyimide
- pyromellitic dianhydride
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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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/1021—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the catalyst used
-
- 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
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
-
- 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
Definitions
- the present invention relates to a solvent-soluble polyimide containing pyromellitic dianhydride, or a solvent-soluble polyimide containing pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride and diaminotoluene,
- the present invention relates to a composition of a block copolymerized polyimide solution of four or more components by a polycondensation under the action of an acid catalyst in a polar solvent, and in particular, a sequential polymerization reaction, and a method for producing the same.
- Polyimide is known as a material that can withstand high temperatures for a long time, and has excellent electrical insulation, mechanical strength, and chemical resistance, and is widely used as a component of electrical and electronic equipment, including the aerospace industry. In particular, it is an essential material in today's semiconductor industry.
- polyimides Today, various polyimides are known, but the first commercially available polyimides are composed of pyromellitic dianhydride (hereinafter referred to as PMDA) and 4,4 'diaminodiphenyl ether (hereinafter referred to as DADE). Polyimide is famous.
- PMDA pyromellitic dianhydride
- DADE 4,4 'diaminodiphenyl ether
- Aromatic polyimides are generally poorly soluble in solvents, and polyimides made from PMDA are known to have particularly low solubility in solvents. Therefore, the conventional method for synthesizing polyimides is to react PMDA with DADE at low temperature in a polar solvent such as N-methylpyrrolidone or N, N-dimethylacetamide to produce a high-molecular-weight, high-viscosity polycondensate. It is common to synthesize a certain polyamic acid (polyimide precursor), heat it to 250-350 ° C, dehydrate it, and make it into a polyimide by a ring-closing reaction (Reference: Polyimide; D. Wilson) , HD Steinberger, PM Morgenrother; Blackie (New York) 1990).
- a polar solvent such as N-methylpyrrolidone or N, N-dimethylacetamide
- Polyamic acids are thermally unstable in solution and are easily decomposed by water. This Therefore, storage stability is poor and it is necessary to store frozen. Polyamic acid has a fast intermolecular exchange reaction in a polar solvent, and even if it is attempted to modify it by adding other components, it becomes a random copolymer and the effect of the modification is small. Since polyamic acid changes even at room temperature,
- Solvent-soluble polyimide can be produced by an imidization reaction directly in solution without passing through a polyamic acid.
- the imidization is carried out by heating to 160 to 200 ° C using sulfuric acid or P-toluenesulfonic acid as an acid catalyst. After the completion of the reaction, the acid catalyst remains in the polyimide solution, causing deterioration of the polymer product. Therefore, it is necessary to separate the catalyst from the polyimide by precipitating, separating and redissolving the polyimide.
- a dehydration-imidation reaction is promoted using an acid-base catalyst utilizing lactone equilibrium.
- a two-component catalyst of valerolactone, pyridine and Z or N-methylmorpholine described in US Pat. No. 5,502,143 can be used. As the imide ratio increases, water is generated, and the water participates in the lactone equilibrium, forming an acid base and exhibiting a catalytic action.
- Polyimides containing PMDA are generally poorly soluble in solvents.
- An object of the present invention is to solubilize this to form a solvent-soluble block copolymer of four or more components.
- the solvent-soluble polyimide can be converted into a multi-component block copolymerized polyimide solution by utilizing a sequential reaction.
- the present invention relates to a composition of a block copolymer polyimide solution containing four or more components containing pyromellitic dianhydride (hereinafter referred to as PMDA) and a method for producing the same.
- PMDA pyromellitic dianhydride
- Another invention of the present invention is a block copolymerized polyimide solution composition
- BTDA henzophenone tetrahydroluponic dianhydride
- DAT diaminotoluene
- Polyimides that are soluble in polar solvents such as N-methylporolidone and N, N-dimethylacetamide are known.
- the solubility of polyimide differs depending on the characteristics, composition and combination of acid dianhydride and aromatic diamine.
- polyimide containing PMDA has low solubility.
- PMDA which indicates the solubility of aromatic polyimide depending on the acid dianhydride.
- Polyimide is the least soluble.
- Polyimides by the combination of PMDA and BTDA are comparatively synthesized by synthesizing polyimides with certain diamines and appropriate compositions. It can be many solvent soluble block polyimides.
- PMD A has a high electron accepting property.
- the idea of the electron donating property, steric bulkiness and steric distortion of aromatic diamine is useful for selecting soluble polyimide.
- Solvents that can be used for the production of polyimide include N-methylpyrrolidone, N-methylformamide, N, N-dimethylformamide, N-methylacetamide, N, N_dimethylacetamide, tetramethylurea, dimethylsulfoxide, Luholan.
- the amount of the polyimide dissolved therein is 10% by weight or more, preferably 15 to 25% by weight.
- a hydrocarbon such as toluene or xylene is added to the above-mentioned polar solvent.
- NMP N-methylpyrrolidone solution
- 2,4-diaminotoluene bis- (3-aminophenoxy) -1,1,3-benzene, bis [(3-aminophenoxy) -1,4-phenyl] sulfone, 3,3,1-diamino-1-diphenylsulfone , 2,2-bis [3-amino-4-phenyloxy] -hexafluoropropane, bis [3-amino-4-phenoxyphenyl] sulfone, 9,9-bis (4-aminophenyl) fluorene, 3 , 5 diamino-benzoic acid, and 4,4 'diamino-3,3'-dioxycarbone-diphenylmethane.
- Example 1 produces a poorly soluble polyimide upon reaction with PMDA.
- Example 2 shows a diamine component that produces a soluble polyimide.
- the molar ratio of the total acid dianhydride to the total aromatic diamine is 1: 1 to 0.95.
- the acid dianhydride used in the second step 6 FDA, BTDA, BPDA, 3,4 dicarboxyphenylsulfone anhydride, bis (3,4 dicarboxyphenyl) ether anhydride, 2, 3, 6 , 7-naphthalenetetracarboxylic anhydride and the like can be used.
- the aromatic diamine used in the second step used in the present invention can be selected from the diamines of Examples 1 and 2.
- a method for producing another block copolymerized polyimide will be described.
- an acid dianhydride other than PMD A (A 2 ) is reacted with an aromatic diamine (B 2 ).
- the molar ratio of A 2 and B 2 is 2: 1. This produces an oligomer of dianhydride at both ends.
- An acid dianhydride selected from the group consisting of anhydrides and the like can be used, and B 2 can be selected from Examples 1 and 2.
- B 4 may be selected from the examples shown 1 and example 2. However, the molar ratio of B 4 / PMDA is 2 to 1.5 / 1.0.
- diaminotoluene (2 to 1.5 mol) is added to PMDA (1 mol) to form an oligomer of diamine at both ends.
- DA-DAT DA-DAT
- BTDA-B BTDA-BJ-BTDA-molar ratio of total acid dianhydride to total aromatic diamine is 1: 1.00-0.95
- BB 2 is from Example 1 and Example 2 You can choose.
- BTDA and DAT can be used as a first step reaction.
- the molar ratio of Jiamin B 3 for PMD A is 1: 1. a 5-2 0..
- the molar ratio of T-PMD A) 2 B 3- total acid dianhydride to total aromatic diamine is 1: 1 to 0.95.
- the aromatic diamine used together with PMDA in the second step can be selected from Examples 1 and 2.
- the block copolymer polyimide solution containing PMDA and the block copolymer polyimide solution containing PMDA, BTDA, and DAT are stable at room temperature and do not easily decompose even when water is added. Therefore, the molecular weight and molecular weight distribution are measured by GPC, and it is easy to reproduce polyimide with an accuracy within 10%.
- polyimide films that are characterized by their structure and type. Examples include polyimide film, insulating varnish, electrodeposited polyimide, photosensitive polyimide, sealant, and adhesive.
- a raw material can be obtained at low cost and easily, and polyimide can be provided at low cost.
- a condensation product of an aromatic diamine having an amino group and a hydroxy group at the ortho position and an aromatic tetracarboxylic dianhydride is not constituted only by a hydroxypolyimide group.
- a polycondensate containing an imido group component and a benzoxazole group component in the molecule is generated.
- Condensates having imido and benzoxazole groups are effective as positive photoresists.
- the benzoxazole group is irradiated with light in the presence of a photoacid generator, and is easily decomposed by development with an alkaline developer to form a positive image.
- Aromatic diamines having an amino group and a phenolic hydroxyl group at the ortho position to each other include 1-hydroxy-2,4 diaminobenzene, 1-hydroxy-1,2,5-diaminobenzene, 3,3 ′ dihydroxybenzidine, 3,3'-dihydroxy-4,4'-diaminodiphenyl ether, 1,4-bis (3-hydroxy-1-amino-phenoxy) benzene, 2,2-bis (4-amino-1-3-hydroxyphenyl) ) Propane, bis (3-amino-4-hydroxyphenyl) propane, bis (3-amino-14-hydroxyphenyl) sulfide, bis (3-amino-14-hydroxyphenyl) sulfone, 2,2,1-bis ( 3-amino-4-hydroxyphenyl) hexafluoropropane.
- the aromatic diamines can be used alone or in combination of two or more.
- the polycondensate containing imide and benzoxazole groups is run and heated to 90 ° C to form a film.
- this film is heat-treated at 300 to 350 ° C, the benzoxazole group is converted into an imide group to form a wholly aromatic polyimide.
- Benzoxazole groups are decomposed to form a positive image upon alkali development.
- a glass-made separable three-necked flask fitted with a stainless steel anchor stirrer was fitted with a cooling tube with a ball equipped with a water separation trap. While passing nitrogen gas, the flask was placed in a silicon oil bath and heated and stirred.
- PMDA Pyromellitic dianhydride
- DAT 2,4 diaminotoluene
- NMP N-methylpyrrolidone
- toluene 30 g are added to a 3-cell flask, and the temperature of the silicon bath is increased while passing nitrogen through. The mixture was heated and stirred at 180 ° C and 180 rpm for 1 hour. Excluding water-toluene fraction 20ml.
- reaction solution A part of the reaction solution was applied on a glass plate, heated at 90 ° C in an infrared oven and dried to obtain a strong film.
- Shimadzu thermal analyzer TGA-50 and scanning heat Thermal analysis of a mass spectrometer (DSC) was performed.
- the thermal decomposition onset temperature was T m 528 ° C
- the 5% weight loss temperature was 504 ° C
- the T g by DSC was unknown.
- a polycondensation solution was prepared in the same manner as in Example 1. ,
- reaction solution was air-cooled after removing the silicon bath, and after 1 hour, 2,2-bis [4- (4-aminophenyl) phenyl] hexafluoropropane 12.97 g (25 mmol), 2,2 —Bis [4- (3-amino-4-hydroxyphenyl)] hexafluoropropane 9.11 (25 mmol) was added, followed by 2,2-bis (3,4-dicarboxyphenyl) 1) 1,1,1,3,3,3-Hexafluoropropane dianhydride 33.32 g (75 mmol) 100 g of NMP and 10 g of toluene are added. The mixture was heated in a silicone oil bath, and stirred at 180 ° C. and 160 rpm for 4 hours to react. A 25% by weight polyimide solution was added. The reaction solution was taken, cast on a glass plate, and dried at 90 ° C to obtain a strong film.
- the molecular weight and molecular weight distribution were measured by GPC.
- T m is 5 1 8 ° C
- T g value by DSC was unknown.
- a polycondensation solution was prepared in the same manner as in Example 1.
- reaction solution A part of the reaction solution was taken and dried into a cast to obtain a strong film.
- the molecular weight was measured by GPC.
- T g could not be confirmed by measurement with DSC.
- a polycondensate was synthesized in the same manner as in Example 1.
- a polycondensate was obtained in the same manner as in Example 1.
- the molecular weight was measured by GPC.
- Thermal analysis was performed.
- the thermal decomposition onset temperature Tm was 531 ° C, and the temperature at which the weight loss was 5% was 537 ° C, and the measurement of Tg by DSC did not give accurate values.
- a polycondensate solution was obtained in the same manner as in Example 1.
- a polyimide solution was synthesized in the same manner as in Example 1.
- 3,4,3,4, -biphenyltetracarboxylic dianhydride 14.72 g (50 mmol), diaminotoluene 3.05 g (25 mmol), valerolactone 1.0 g (10 mmol), pyridine 1. Charge '6 g (20 mmol), 100 g of NMP and 30 g of toluene. After stirring at room temperature for 1 hour in a nitrogen stream, the mixture was heated and stirred at 180 ° C and 170 rpm for 1 hour.
- the molecular weight was measured by GPC. M55, 800, Mn 23, 200, Mw 71, 200, Mz 282, 300
- the polyimide solution dissolved in NMP of Example 2 was diluted with NMP from 25% by weight to 15% by weight.
- 20 g (polyimide content: 3 g) of the solution filtered using a 1-micron pore filtration membrane was added to the photoacid generator (2,3,4-trihydroxybenzophenone and 1,2-naphthoquinone_2-diazido-5).
- —0.6 g of sulfonic acid was added in the dark to make a homogeneous solution.
- This solution was applied to the surface of a silicon wafer having a diameter of 5 cm by spin coating.
- Example 6 20 g of the polyimide solution (20% by weight) of Example 6 was added, 2 g of anisol was added thereto, and the mixture was filtered with a filtration membrane having a pore size of 1 micron.
- Photoacid generator (2, 0.2 g of 3,4-trihydroxybenzophenone and 1,2-naphthoquinone-12-diazide-15-sulfonic acid ester) was added in the dark to make a homogeneous solution.
- a film was formed by spin coating on a silicon wafer and heat-treated at 90 ° C. for 10 minutes to obtain a film of 5.33 ⁇ m.
- Example 7 The polyimide solution (20% weight) of Example 7, which was processed in the same manner as in Example 8 to form a positive image, was diluted to 15% by weight with NMP. To 20 g of this solution, 0.6 of 1,3,4-naphthoquinone-12-diamid-15-sulfonic acid ester of 2,3,4-trihydroxybenzophenone was added and dissolved. This solution was spin-coated on a silicon wafer (5 cm diameter). [Spin coating conditions: 5 seconds (stop) 1-20 seconds (200 r. P.m.) 1 5 seconds (stop) 1 30 seconds (30000 r. P.m.)-5 seconds (stop)]. The film was heated at 90 ° C. for 10 minutes to form a film of 5.07 ⁇ m.
- a glass-cooled three-necked flask equipped with a stainless steel anchor stirrer was fitted with a cooling tube with a ball equipped with a water separation trap.
- the flask was immersed in a silicone oil solution and heated and stirred while passing nitrogen gas.
- PMD A Pyromellitic dianhydride 10.9 lg (50 mmol), 9.17 g (25 mmol) of 2,4-diaminotoluene (hereinafter referred to as DAT), 1.0 g (10 mmol) of ⁇ -valerolactone, 1.6 g (20 mmol) of pyridine, N-methylpyrrolidone ( After that, 100 g of toluene and 30 g of toluene are charged. After stirring at room temperature for 1 hour at 160 rpm, the mixture is heated and stirred at 180 ° C and 156 rpm for 1 hour. Excluding 15 ml of toluene-water.
- BTDA 3,4,3 ', 4'-benzophenonetetracarboxylic dianhydride 16.2 g, 3,3'-dimethylbenzidine 5.3 1 g (25 mmol) was added, 90 g of NMP and 10 g of toluene were added, and the mixture was stirred at room temperature for 30 minutes.
- reaction solution A part of the reaction solution was cast on a glass plate, and heated in an infrared oven at 90 ° C for 1 hour and at 180 ° C for 1 hour to obtain a yellow-brown film.
- Thermal analysis was performed with a Shimadzu thermal folding apparatus TG A-50 and a differential scanning calorimeter (DSC).
- the thermal decomposition onset temperature T m was 509 ° C.
- the glass transition temperature T g by DSC was not clear.
- the decomposition onset temperature Tm was 525 ° C, and the temperature at which the weight was reduced by 5% was 325 ° C.
- the glass transition temperature Tg due to DSC was unclear.
- Thermal analysis was performed. Thermal decomposition onset temperature Tm484 ° (The temperature at which the 5% weight loss was reached was 478 ° C.
- reaction time is as short as 1 hour and 30 minutes, the film properties are slightly poor. Therefore, heating for 3 hours or more is necessary to obtain a strong film.
- BTDA1 6.12 g (50 mmol), 2,2-bis [4- (4-aminophenoxy) phenyl] propane 10.27 g (25 mmol), norelolactone 1.0 g (10 mmol), pyridine 1 6 g (20 mmol), NMP100 and 30 g of toluene are charged, and stirred and dissolved at room temperature at 155 rpm for 1 hour. Then, heat and stir at 175 ° C and 155 rpm for 1 hour, and stir at room temperature for 30 minutes.
- the glass transition temperature Tg by DSC was 223 ° C. '
- Polyimides containing PMDA are generally poorly soluble in solvents.
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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JP2004544725A JPWO2004035689A1 (ja) | 2002-10-16 | 2003-02-28 | ピロメリット酸ジ無水物を含むブロック共重合ポリイミド溶液組成物及びその製造方法 |
EP03707181A EP1561786A4 (en) | 2002-10-16 | 2003-02-28 | COMPOSITIONS OF COPOLYIMIDE SEQUENCES COMPRISING PYROMELLIIC DIANHYDRIDE AND PROCESS FOR PRODUCING THE SAME |
US10/531,165 US20060004180A1 (en) | 2002-10-16 | 2003-02-28 | Solution compositions of block copolyimides comprising pyromellitic dianhydride and process for production thereof |
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JP2002301700 | 2002-10-16 | ||
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JP2002-301702 | 2002-10-16 |
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JP2008107512A (ja) * | 2006-10-25 | 2008-05-08 | Sumitomo Bakelite Co Ltd | ポジ型感光性樹脂組成物 |
WO2008120398A1 (ja) * | 2007-04-03 | 2008-10-09 | Solpit Industries, Ltd. | 溶剤に可溶な6,6-ポリイミド共重合体及びその製造方法 |
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WO2011001493A1 (ja) * | 2009-06-29 | 2011-01-06 | ソルピー工業株式会社 | 有機溶媒に可溶な、pmda、dade、da、ビス(アミノ-4-ヒドロキシフェニル)スルホン成分を含むポリイミドおよびその製造方法 |
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- 2003-02-28 WO PCT/JP2003/002343 patent/WO2004035689A1/ja not_active Application Discontinuation
- 2003-02-28 US US10/531,165 patent/US20060004180A1/en not_active Abandoned
- 2003-02-28 JP JP2004544725A patent/JPWO2004035689A1/ja active Pending
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JP2008058707A (ja) * | 2006-08-31 | 2008-03-13 | Asahi Kasei Electronics Co Ltd | ポジ型感光性樹脂組成物 |
JP2008107512A (ja) * | 2006-10-25 | 2008-05-08 | Sumitomo Bakelite Co Ltd | ポジ型感光性樹脂組成物 |
WO2008120398A1 (ja) * | 2007-04-03 | 2008-10-09 | Solpit Industries, Ltd. | 溶剤に可溶な6,6-ポリイミド共重合体及びその製造方法 |
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WO2008155811A1 (ja) * | 2007-06-18 | 2008-12-24 | Solpit Industries, Ltd. | 6,6-ポリイミド共重合体及びその製造方法 |
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WO2011001493A1 (ja) * | 2009-06-29 | 2011-01-06 | ソルピー工業株式会社 | 有機溶媒に可溶な、pmda、dade、da、ビス(アミノ-4-ヒドロキシフェニル)スルホン成分を含むポリイミドおよびその製造方法 |
JP5523456B2 (ja) * | 2009-06-29 | 2014-06-18 | ソルピー工業株式会社 | 有機溶媒に可溶な、pmda、dade、da、ビス(アミノ−4−ヒドロキシフェニル)スルホン成分を含むポリイミドおよびその製造方法 |
KR101472328B1 (ko) * | 2009-06-29 | 2014-12-12 | 소루피 고교 가부시키가이샤 | 유기 용매에 가용인, PMDA (pyromellitic dianhydride), DADE (diaminodiphenyl ether), DA (carboxylic dianhydride), 비스(아미노-4-하이드록시페닐)술폰 성분을 함유하는 폴리이미드 및 그 제조 방법 |
KR20120003667A (ko) * | 2010-07-05 | 2012-01-11 | 삼성정밀화학 주식회사 | 열경화성 수지 제조용 조성물 및 그의 경화물, 상기 경화물을 포함하는 프리프레그와 프리프레그 적층체, 및 상기 프리프레그 또는 프리프레그 적층체를 채용한 금속박 적층판과 프린트 배선판 |
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Also Published As
Publication number | Publication date |
---|---|
US20060004180A1 (en) | 2006-01-05 |
EP1561786A1 (en) | 2005-08-10 |
JPWO2004035689A1 (ja) | 2006-02-16 |
EP1561786A4 (en) | 2007-07-18 |
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