JP2589054B2 - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JP2589054B2 JP2589054B2 JP17694894A JP17694894A JP2589054B2 JP 2589054 B2 JP2589054 B2 JP 2589054B2 JP 17694894 A JP17694894 A JP 17694894A JP 17694894 A JP17694894 A JP 17694894A JP 2589054 B2 JP2589054 B2 JP 2589054B2
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- JP
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- Prior art keywords
- dianhydride
- resin composition
- bis
- thermosetting resin
- weight
- 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.)
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- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は接着フィルム、積層材
料、あるいは成形材料等に用いることのできる耐熱性に
優れた熱硬化性樹脂組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a thermosetting resin composition having excellent heat resistance which can be used for an adhesive film, a laminated material, a molding material, or the like.
【０００２】[0002]
【従来の技術】従来から、ポリイミド樹脂は耐熱性、電
気絶縁性、耐薬品性に優れた性能を有するため、産業上
広く利用されている。ポリイミド樹脂の中でテトラカル
ボン酸二無水物とジアミンの反応によりポリアミド酸を
経由して得られる縮合型のポリイミド樹脂は優れた特性
を示すものが多いが、その軟化温度が高く、加工性に乏
しいという欠点を有している。また耐熱性をある程度犠
牲にして、加工性を改良した熱可塑性のポリエーテルイ
ミド（商品名「ウルテム」ゼネラル エレクトリック社
製）も知られているが、耐熱性及び耐薬品性の面で充分
なものではなかった。一方、ビスマレイミド化合物を単
独で重合させる付加型のポリイミド樹脂は熱的性質にお
いては優れているが、機械的強度に劣るため、流延して
フィルムとすることができなかった。2. Description of the Related Art Hitherto, polyimide resins have been widely used in industry because of their excellent properties in heat resistance, electrical insulation and chemical resistance. Polyimide resins obtained via polyamic acid by the reaction of tetracarboxylic dianhydride and diamine among polyimide resins often have excellent properties, but their softening temperature is high and their workability is poor. There is a disadvantage that. Also known is a thermoplastic polyetherimide (trade name "Ultem" manufactured by General Electric Co., Ltd.) with improved workability at the expense of heat resistance to some extent, but which has sufficient heat resistance and chemical resistance. Was not. On the other hand, an addition type polyimide resin obtained by polymerizing a bismaleimide compound alone is excellent in thermal properties, but poor in mechanical strength, and thus could not be cast into a film.
【０００３】[0003]
【発明が解決しようとする課題】本発明はこれらの欠点
を鑑みてなされたもので、熱硬化前にはフィルム等に成
形でき、硬化後は強靭で可撓性、接着性ならびに耐熱性
に優れた熱硬化性樹脂組成物を提供するものである。SUMMARY OF THE INVENTION The present invention has been made in view of these drawbacks, and can be formed into a film or the like before thermosetting, and is tough and excellent in flexibility, adhesion and heat resistance after curing. And a thermosetting resin composition.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、前記目的
を達成するために鋭意研究を行なった結果、後述の熱硬
化性樹脂組成物が耐熱性、機械的特性、加工性に優れて
いることを見出し、本発明を完成したものである。Means for Solving the Problems The present inventors have conducted intensive studies to achieve the above object, and as a result, the thermosetting resin composition described below has excellent heat resistance, mechanical properties and workability. That is, the present invention has been completed.
【０００５】すなわち、本発明の熱硬化性樹脂組成物
は、一般式（Ｉ）That is, the thermosetting resin composition of the present invention has the general formula (I)
【化３】 から成る群より選ばれた少なくとも１種の基を表し、 を表し、Ｙは からなる群より選ばれた４価の基を表す。）で表される
繰り返し単位を有する重合体１００重量部と 式（ＩＩ）Embedded image Represents at least one group selected from the group consisting of And Y is Represents a tetravalent group selected from the group consisting of 100 parts by weight of a polymer having a repeating unit represented by the formula (II):
【化４】 で表されるＮ，Ｎ′−４，４′−ジフェニルメタンビス
マレイミド５〜１００重量部よりなる熱硬化性樹脂組成
物である。Embedded image Is a thermosetting resin composition comprising 5 to 100 parts by weight of N, N'-4,4'-diphenylmethanebismaleimide.
【０００６】[0006]
【化５】本発明において使用する重合体は式（ＩＩＩ） に示すジアミン化合物に一種以上のテトラカルボン酸二
無水物を通常公知の方法により反応させて得られるポリ
アミド酸及び／又はこれを更に脱水環化して得られるポ
リイミドである。The polymer used in the present invention has the formula (III) And polyamic acids obtained by reacting one or more tetracarboxylic dianhydrides with the diamine compound shown in (1) by a generally known method and / or a polyimide obtained by further dehydration cyclization thereof.
【０００７】重合体の一成分であるジアミン化合物は具
体的には、１，３−ビス（３−アミノフェノキシ）ベン
ゼン、ビス〔４−（３−アミノフェノキシ）フェニル〕
メタン、１，１−ビス〔４−（３−アミノフェノキシ）
フェニル〕エタン、１，２−ビス〔４−（３−アミノフ
ェノキシ）フェニル〕エタン、２，２−ビス〔〔４−
（３−アミノフェノキシ）フェニル〕プロパン、２，２
−ビス〔４−（３−アミノフェノキシ）フェニル〕ブタ
ン、２，２−ビス〔４−（３−アミノフェノキシ）フェ
ニル〕−１，１，１，３，３，３−ヘキサフルオロプロ
パン、ビス〔４−（３−アミノフェノキシ）フェニル〕
スルフィド等があげられ、これらは単独あるいは二種以
上混合して用いられる。The diamine compound which is one component of the polymer is, specifically, 1,3-bis (3-aminophenoxy) benzene, bis [4- (3-aminophenoxy) phenyl]
Methane, 1,1-bis [4- (3-aminophenoxy)
Phenyl] ethane, 1,2-bis [4- (3-aminophenoxy) phenyl] ethane, 2,2-bis [[4-
(3-aminophenoxy) phenyl] propane, 2,2
-Bis [4- (3-aminophenoxy) phenyl] butane, 2,2-bis [4- (3-aminophenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane, bis [ 4- (3-aminophenoxy) phenyl]
Sulfides and the like are used, and these are used alone or in combination of two or more.
【０００８】また、もう一方の成分であるテトラカルボ
ン酸二無水物は式（ＩＶ）The other component, tetracarboxylic dianhydride, has the formula (IV)
【化６】 で表され、具体的には、エチレンテトラカルボン酸二無
水物、ブタンテトラカルボン酸二無水物、シクロペンタ
ンテトラカルボン酸二無水物、ピロメリット酸二無水
物、１，２，３，４−ベンゼンテトラカルボン酸二無水
物、３，３′，４，４′−ベンゾフェノンテトラカルボ
ン酸二無水物、２，２′，３，３′−ベンゾフェノンテ
トラカルボン酸二無水物、３，３′，４，４′−ビフェ
ニルテトラカルボン酸二無水物、２，２′，３，３′−
ビフェニルテトラカルボン酸二無水物、２，２−ビス
（３，４−ジカルボキシフェニル）プロパン二無水物、
２，２−ビス（２，３−ジカルボキシフェニル）プロパ
ン二無水物、ビス（３，４−ジカルボキシフェニル）エ
ーテル二無水物、ビス（３，４−カルボキシフェニル）
スルホン二無水物、１，１−ビス（２，３−ジカルボキ
シフェニル）エタン二無水物、ビス（２，３−ジカルボ
キシフェニル）メタン二無水物、ビス（３，４−ジカル
ボキシフェニル）メタン二無水物、４，４′−（ｐ−フ
ェニレンジオキシ）ジフタル酸二無水物、４，４′−
（ｍ−フェニレンジオキシ）ジフタル酸二無水物、２，
３，６，７−ナフタレンテトラカルボン酸二無水物、
１，４，５，８−ナフタレンテトラカルボン酸二無水
物、１，２，５，６−ナフタレンテトラカルボン酸二無
水物、３，４，９，１０−ペリレンテトラカルボン酸二
無水物、２，３，６，７−アントラセンテトラカルボン
酸二無水物、１，２，７，８−フェナントレンテトラカ
ルボン酸二無水物等であり、これらテトラカルボン酸二
無水物は単独あるいは２種以上混合して用いられる。Embedded image Specifically, ethylene tetracarboxylic dianhydride, butane tetracarboxylic dianhydride, cyclopentane tetracarboxylic dianhydride, pyromellitic dianhydride, 1,2,3,4-benzene Tetracarboxylic dianhydride, 3,3 ', 4,4'-benzophenonetetracarboxylic dianhydride, 2,2', 3,3'-benzophenonetetracarboxylic dianhydride, 3,3 ', 4 4'-biphenyltetracarboxylic dianhydride, 2,2 ', 3,3'-
Biphenyltetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride,
2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, bis (3,4-carboxyphenyl)
Sulfone dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (2,3-dicarboxyphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) methane Dianhydride, 4,4 '-(p-phenylenedioxy) diphthalic dianhydride, 4,4'-
(M-phenylenedioxy) diphthalic dianhydride, 2,
3,6,7-naphthalenetetracarboxylic dianhydride,
1,4,5,8-naphthalenetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 2, 3,6,7-anthracenetetracarboxylic dianhydride, 1,2,7,8-phenanthrenetetracarboxylic dianhydride and the like. These tetracarboxylic dianhydrides may be used alone or as a mixture of two or more. Can be
【０００９】前記式（II）で表されるＮ，Ｎ′−４，
４′−ジフェニルメタンビスマレイミドは、通常公知の
方法により４，４′−ジアミノフェニルメタンと無水マ
レイン酸を縮合・脱水反応して、容易に製造できる。The N, N'-4,
4'-diphenylmethanebismaleimide can be easily produced by a condensation / dehydration reaction of 4,4'-diaminophenylmethane and maleic anhydride by a generally known method.
【００１０】前記（Ｉ）式の重合体と（II）式のビスマ
レイミド化合物の混合割合は、重合体（Ｉ）１００重量
部に対してビスマレイミド化合物（II）を５〜１００重
量部、好ましくは１０〜８０重量部を使用する。ビスマ
レイミド化合物の配合量が５重量部より少ないと本発明
の目的とする加工性、機械的特性の改良に効果はなく、
また１００重量部より多いと硬化物がもろくなり、成形
性も悪くなる。The mixing ratio of the polymer of the formula (I) and the bismaleimide compound of the formula (II) is preferably 5 to 100 parts by weight of the bismaleimide compound (II) per 100 parts by weight of the polymer (I). Uses 10 to 80 parts by weight. If the amount of the bismaleimide compound is less than 5 parts by weight, there is no effect on the processability and mechanical properties aimed at by the present invention,
On the other hand, if the amount is more than 100 parts by weight, the cured product becomes brittle, and the moldability deteriorates.
【００１１】重合体（Ｉ）とビスマレイミド化合物（I
I）の混合は粉状で行なってもよいが通常はポリアミド
酸及び／又はポリイミドのワニスあるいは懸濁液中にビ
スマレイミド化合物（II）を添加溶解することによって
行なわれる。The polymer (I) and a bismaleimide compound (I
The mixing of I) may be carried out in powder form, but is usually carried out by adding and dissolving the bismaleimide compound (II) in a varnish or suspension of polyamic acid and / or polyimide.
【００１２】このようにして得た樹脂組成物はガラス
布、カーボンクロス等の基材に含浸、乾燥してプリプレ
グとして用いることもできるし、ガラス板、ステンレス
板等に流延、乾燥してフィルム状接着剤として各種用途
に用いることもできる。この場合、乾燥温度はビスマレ
イミド化合物の重合が顕著になる温度よりも低く保つ必
要があり、乾燥時間については、残存溶剤の量が本発明
の目的を損なわない程度になるようにしなければならな
い。また、粉状のまま、成形材料として用いることもで
きる。本発明の樹脂組成物を加熱硬化することによって
強靭な耐熱性成形物が得られる。The resin composition thus obtained can be used as a prepreg by impregnating and drying a substrate such as glass cloth or carbon cloth, or cast on a glass plate or a stainless steel plate and dried to form a film. It can also be used for various applications as a sticky adhesive. In this case, the drying temperature must be kept lower than the temperature at which the polymerization of the bismaleimide compound becomes remarkable, and the drying time must be such that the amount of the residual solvent does not impair the object of the present invention. Further, it can be used as a molding material in powder form. By heating and curing the resin composition of the present invention, a tough, heat-resistant molded article can be obtained.
【００１３】本発明の熱硬化性樹脂組成物は必要に応じ
て重合触媒を添加してもよい。該触媒の使用量は特に限
定しないが重合物全重量を基準として０．００１〜１０
重量％、特に０．１〜５重量％の範囲が好ましい。重合
触媒としては、過酸化ベンゾイル、ｔ−ブチルヒドロペ
ルオキシド、ジクミルパーオキサイド、アゾビスイソブ
チロニトリル、アゾビスシクロヘキサンカルボニトリル
等の公知のフリーラジカル触媒が有効である。なお重合
触媒は適宜組み合わせて用いても良い。The thermosetting resin composition of the present invention may optionally contain a polymerization catalyst. The amount of the catalyst used is not particularly limited, but is 0.001 to 10 based on the total weight of the polymer.
% By weight, especially in the range of 0.1 to 5% by weight. As the polymerization catalyst, known free radical catalysts such as benzoyl peroxide, t-butyl hydroperoxide, dicumyl peroxide, azobisisobutyronitrile, and azobiscyclohexanecarbonitrile are effective. The polymerization catalysts may be used in appropriate combination.
【００１４】[0014]
【実施例】以下、本発明を実施例により説明する。The present invention will be described below with reference to examples.
【００１５】実施例１Ａ 撹拌機、還流冷却器および窒素導入管を備えた容器にビ
ス〔４−（３−アミノフェノキシ）フェニル〕スルフィ
ド８０．０ｇ（０．２モル）とＮ，Ｎ−ジメチルアセト
アミド４９２．８ｇを装入し、室温で窒素雰囲気下にピ
ロメリット酸二無水物４３．２ｇ（０．１９８モル）を
溶液温度の上昇に注意しながら分割して加え、さらに室
温で約２０時間かきまぜ、樹脂分２０．０％、２５℃で
の溶液粘度６６ポイズのポリアミド酸ワニスを得た。得
られたワニスはＮ，Ｎ−ジメチルアセトアミドで希釈
し、ポリアミド酸の濃度０．５％、３５℃で対数粘度は
０．８６dl／ｇであった。このポリアミド酸ワニス１０
０ｇにＮ，Ｎ′−４，４′−ジフェニルメタンビスマレ
イミドを表１に示す量を添加して、樹脂分で２０．０％
になるようにＮ，Ｎ−ジメチルアセトアミドを加え、室
温にて溶解した。この樹脂組成物をガラス板上に流延
し、窒素雰囲気下１３０℃で１時間、さらに１８０℃で
２時間乾燥して厚さ２５μｍの柔軟な褐色透明の未硬化
フィルムを得た。この未硬化フィルムは２５０℃で３０
分加熱することによって強靭な硬化フィルムが得られ
た。未硬化フィルムの軟化点（ＴＭＡ針入法）及び未硬
化フィルムを予備加熱したスチール（冷間圧延鋼、ＪＩ
Ｓ−３１４１，ＳＰＥＣ／ＳＤ，２５×１００×１．６
mm）間に挿入し、２５０℃、２０kg／cm2で３０分間加
圧圧着させたものの２５℃及び２４０℃高温下での引張
剪断力（測定方法はＪＩＳ−Ｋ−６８４８およびＫ−６
８５０に拠る）の値を表１に示した。Example 1A 80.0 g (0.2 mol) of bis [4- (3-aminophenoxy) phenyl] sulfide and N, N-dimethylacetamide were placed in a vessel equipped with a stirrer, reflux condenser and nitrogen inlet tube. 492.8 g was charged, and 43.2 g (0.198 mol) of pyromellitic dianhydride was added in portions at room temperature under a nitrogen atmosphere while paying attention to the rise in solution temperature, and the mixture was further stirred at room temperature for about 20 hours. A polyamic acid varnish having a resin content of 20.0% and a solution viscosity at 25 ° C. of 66 poise was obtained. The obtained varnish was diluted with N, N-dimethylacetamide to have a polyamic acid concentration of 0.5% and an logarithmic viscosity at 35 ° C. of 0.86 dl / g. This polyamic acid varnish 10
To 0 g, N, N'-4,4'-diphenylmethanebismaleimide was added in the amount shown in Table 1, and the resin content was 20.0%.
N, N-dimethylacetamide was added to the mixture and dissolved at room temperature. This resin composition was cast on a glass plate and dried under a nitrogen atmosphere at 130 ° C. for 1 hour and further at 180 ° C. for 2 hours to obtain a flexible brown transparent uncured film having a thickness of 25 μm. This uncured film is 30
By heating for a minute, a tough cured film was obtained. Softening point of uncured film (TMA penetration method) and preheated uncured film of steel (cold rolled steel, JI
S-3141, SPEC / SD, 25 × 100 × 1.6
mm) and press-bonded at 250 ° C. and 20 kg / cm 2 for 30 minutes, but tensile shear force at a high temperature of 25 ° C. and 240 ° C. (measurement methods are JIS-K-6848 and K-6).
850) are shown in Table 1.
【００１６】実施例２Ａ〜８Ａ及び比較例１Ａ〜２Ａ 表１および表２に示すジアミン化合物とテトラカルボン
酸二無水物を各々表１および表２に示すモル数を使用
し、実施例１Ａと同様の操作をして、ポリアミド酸ワニ
スを得た。これにビスマレイミド化合物を表１および表
２に示す量溶解させ、樹脂組成物ワニスを得た。以下、
実施例１Ａと同様の操作をして表１および表２の結果を
得た。Examples 2A to 8A and Comparative Examples 1A to 2A The diamine compounds and the tetracarboxylic dianhydrides shown in Tables 1 and 2 were used in the same manner as in Example 1A, using the moles shown in Tables 1 and 2 respectively. To obtain a polyamic acid varnish. The bismaleimide compound was dissolved therein in the amounts shown in Tables 1 and 2 to obtain a resin composition varnish. Less than,
By performing the same operation as in Example 1A, the results shown in Tables 1 and 2 were obtained.
【００１７】[0017]
【表１】 [Table 1]
【表２】 [Table 2]
【００１８】実施例１Ｂ 撹拌機、還流冷却器および窒素導入管を備えた容器にビ
ス〔４−（３−アミノフェノキシ）フェニル〕スルフィ
ド８００ｇ（２モル）とＮ，Ｎ−ジメチルアセトアミド
４９２８ｇを装入し、窒素雰囲気下において、ピロメリ
ット酸二無水物４３６．３ｇ（２モル）を溶液温度の上
昇に注意しながら分割して加え、室温で約２０時間かき
まぜた。斯くして得られたポリアミド酸溶液に、６０．
６ｇのトリエチルアミンおよび６１．２ｇの無水酢酸を
約３０分かけて添加し、その後約３０分かきまぜた。こ
の溶液に４０００ｇのメタノールを加え、３０℃におい
てポリイミド粉をろ別した。得られたポリイミド粉をメ
タノールおよびアセトンで洗浄したのち、窒素雰囲気下
に２００℃で１６時間乾燥して、１１５３ｇのポリイミ
ド粉を得た。上記ポリイミド粉１０ｇに、Ｎ，Ｎ′−
４，４′−ジフェニルメタンビスマレイミド１．０ｇを
加え均一混合した後、２５０℃に加熱した１２５×１
２．５×３．２mmの金型に圧入した後、３５０℃×５０
kg／cm2×５minで圧縮成形して曲げ試験片を得た。得ら
れた試験片をＡＳＴＭ Ｄ−６３８に準じて、室温下で
の曲げ強度及び曲げ弾性率を測定し表３の結果を得た。Example 1B 800 g (2 mol) of bis [4- (3-aminophenoxy) phenyl] sulfide and 4928 g of N, N-dimethylacetamide were charged into a vessel equipped with a stirrer, reflux condenser and nitrogen inlet tube. Then, under a nitrogen atmosphere, 436.3 g (2 mol) of pyromellitic dianhydride was added portionwise while paying attention to an increase in the solution temperature, and the mixture was stirred at room temperature for about 20 hours. In the polyamic acid solution thus obtained, 60.
6 g of triethylamine and 61.2 g of acetic anhydride were added over about 30 minutes, followed by stirring for about 30 minutes. 4000 g of methanol was added to this solution, and the polyimide powder was filtered off at 30 ° C. After washing the obtained polyimide powder with methanol and acetone, it was dried at 200 ° C. for 16 hours under a nitrogen atmosphere to obtain 1153 g of polyimide powder. N, N'-
After adding 1.0 g of 4,4'-diphenylmethane bismaleimide and mixing uniformly, the mixture was heated to 250 ° C. and 125 × 1
After being pressed into a 2.5 × 3.2 mm mold, 350 ° C. × 50
A compression test was performed at kg / cm 2 × 5 min to obtain a bending test piece. The flexural strength and flexural modulus at room temperature of the obtained test piece were measured according to ASTM D-638, and the results shown in Table 3 were obtained.
【００１９】実施例２Ｂ〜実施例４Ｂ及び比較例１Ｂ〜
比較例２Ｂ 表３に示すジアミン成分とテトラカルボン酸成分をそれ
ぞれ、実施例１Ｂと同じモル比でかつ同様の操作でポリ
イミド粉を得た。得られたポリイミド粉に対して、表３
に示すビスマレイミド成分を同表に示す重量比で実施例
１Ｂと全く同じ操作で混合し、かつ同じ操作で曲げ強度
及び曲げ弾性率を測定した。結果を表３に併せて示す。
但し、比較例１Ｂ及び比較例２Ｂについてはビスマレイ
ミド成分は混合せず、表３の原料より得られたポリイミ
ド粉の曲げ強度及び曲げ弾性率を測定した。Examples 2B to 4B and Comparative Examples 1B to
Comparative Example 2B A diamine component and a tetracarboxylic acid component shown in Table 3 were each obtained in the same molar ratio as in Example 1B and by the same operation to obtain a polyimide powder. Table 3 shows the obtained polyimide powder.
Were mixed by the same operation as in Example 1B at the weight ratios shown in the same table, and the flexural strength and flexural modulus were measured by the same operation. The results are shown in Table 3.
However, the flexural strength and flexural modulus of the polyimide powder obtained from the raw materials in Table 3 were measured without mixing the bismaleimide component in Comparative Example 1B and Comparative Example 2B.
【００２０】[0020]
【表３】 [Table 3]
【００２１】[0021]
【発明の効果】本発明の熱硬化性樹脂組成物は、接着
性、成形性、可撓性、および耐熱性に優れたもので接着
剤、積層板、成形材料として電気・電子機器等に使用さ
れるなど広くその用途が期待され、産業上の利用効果は
大きい。The thermosetting resin composition of the present invention is excellent in adhesiveness, moldability, flexibility and heat resistance and is used as an adhesive, a laminate, and a molding material for electric and electronic equipment. It is expected to be widely used, and has a great industrial use effect.
Claims (1)
繰り返し単位を有する重合体１００重量部と式（ＩＩ） 【化２】 で表されるＮ，Ｎ′−４，４′−ジフェニルメタンビス
マレイミド５〜１００重量部からなる熱硬化性樹脂組成
物。1. A compound of the general formula (I) Represents at least one group selected from the group consisting of And Y is Represents a tetravalent group selected from the group consisting of ) And 100 parts by weight of a polymer having a repeating unit represented by the formula (II): A thermosetting resin composition comprising 5 to 100 parts by weight of N, N'-4,4'-diphenylmethanebismaleimide represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17694894A JP2589054B2 (en) | 1994-07-28 | 1994-07-28 | Thermosetting resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17694894A JP2589054B2 (en) | 1994-07-28 | 1994-07-28 | Thermosetting resin composition |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63203717A Division JPH07122002B2 (en) | 1988-05-17 | 1988-08-18 | Thermosetting resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0776652A JPH0776652A (en) | 1995-03-20 |
| JP2589054B2 true JP2589054B2 (en) | 1997-03-12 |
Family
ID=16022534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17694894A Expired - Lifetime JP2589054B2 (en) | 1994-07-28 | 1994-07-28 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2589054B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009067745A (en) * | 2007-09-14 | 2009-04-02 | Jsr Corp | New diamine compound, and polyamic acid and imidized polymer produced by using the same |
-
1994
- 1994-07-28 JP JP17694894A patent/JP2589054B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0776652A (en) | 1995-03-20 |
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