JPH05301972A - Production of bonded composite body of thermosetting resin and rubber - Google Patents
Production of bonded composite body of thermosetting resin and rubberInfo
- Publication number
- JPH05301972A JPH05301972A JP10755992A JP10755992A JPH05301972A JP H05301972 A JPH05301972 A JP H05301972A JP 10755992 A JP10755992 A JP 10755992A JP 10755992 A JP10755992 A JP 10755992A JP H05301972 A JPH05301972 A JP H05301972A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- composition
- epoxy resin
- molding material
- uncured
- 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.)
- Pending
Links
Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Laminated Bodies (AREA)
- Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、エポキシ樹脂組成物と
アクリロニトリル・ブタジエン共重合体含有ゴム組成物
又は水素添加アクリロニトリル−ブタジエン共重合体ゴ
ム、メタクリル酸、酸化亜鉛及び有機過酸化物を含有す
るゴム組成物からなる未加硫の成形材料ととからなる接
着複合体の製造方法に関する。TECHNICAL FIELD The present invention contains an epoxy resin composition and an acrylonitrile-butadiene copolymer-containing rubber composition or a hydrogenated acrylonitrile-butadiene copolymer rubber, methacrylic acid, zinc oxide and an organic peroxide. The present invention relates to a method for producing an adhesive composite comprising a rubber composition and an unvulcanized molding material.
【０００２】[0002]
【従来の技術】エポキシ樹脂組成物は、接着剤や繊維強
化プラスチックのマトリックス樹脂として広く使用され
ている。このエポキシ樹脂組成物をマトリックス樹脂と
する繊維強化プラスチックは、強度、剛性（弾性）等の
機械的性質が極めて優れ、しかも、軽量であるため、こ
れを汎用ゴムに強固に接着一体化することができれば、
汎用ゴムの強度や剛性を高め、しかも、重量を低減する
ことができ、汎用ゴム製品の性能を向上し、用途を拡大
することが可能である。しかしながら、一般のエポキシ
樹脂組成物の硬化物は汎用ゴムに対する接着性に欠ける
ため、耐久性のある接着複合体を製造することができな
かった。BACKGROUND OF THE INVENTION Epoxy resin compositions are widely used as adhesives and matrix resins for fiber reinforced plastics. Fiber-reinforced plastics using this epoxy resin composition as a matrix resin have excellent mechanical properties such as strength and rigidity (elasticity) and are lightweight, so that they can be firmly bonded and integrated with general-purpose rubber. if you can,
It is possible to increase the strength and rigidity of a general-purpose rubber, reduce the weight thereof, improve the performance of a general-purpose rubber product, and expand its applications. However, since a cured product of a general epoxy resin composition lacks adhesiveness to general-purpose rubber, a durable adhesive composite cannot be manufactured.
【０００３】本発明者は、エポキシ樹脂組成物と各種の
汎用ゴムとの接着性について鋭意検討した結果、汎用ゴ
ムの中でも、特に未加硫のアクリロニトリル・ブタジエ
ン共重合体含有ゴム組成物（以下，ＮＢＲ組成物と称す
る）又は水素添加アクリロニトリル−ブタジエン共重合
体ゴム、メタクリル酸、酸化亜鉛及び有機過酸化物を含
有するゴム組成物（以下水素添加ＮＢＲ組成物と称す
る）に対しては、未硬化エポキシ樹脂組成物を硬化させ
ると同時に接着させることが可能であることを見出し、
本発明を為すに到ったものである。As a result of earnest studies on the adhesiveness between the epoxy resin composition and various general-purpose rubbers, the present inventor has found that among general-purpose rubbers, a rubber composition containing an unvulcanized acrylonitrile-butadiene copolymer (hereinafter, NBR composition) or a hydrogenated acrylonitrile-butadiene copolymer rubber, a rubber composition containing methacrylic acid, zinc oxide and an organic peroxide (hereinafter referred to as a hydrogenated NBR composition), uncured. It was found that it is possible to bond the epoxy resin composition while curing it,
The present invention has been accomplished.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、エポ
キシ樹脂組成物からなる成形材料とＮＢＲ組成物又は水
素添加ＮＢＲ組成物からなる成形材料とが強固に接着一
体化した接着複合体の製造方法を提供することにある。An object of the present invention is to produce an adhesive composite in which a molding material composed of an epoxy resin composition and a molding material composed of an NBR composition or a hydrogenated NBR composition are firmly bonded and integrated. To provide a method.
【０００５】[0005]
【発明が解決しようとする課題】このような目的を達成
する本発明の方法は、エポキシ樹脂組成物からなる未硬
化の材料又は未硬化成形材料と、ＮＢＲ組成物又は水素
添加ＮＢＲ組成物からなる未加硫の成形材料とを積層加
熱し、硬化接着一体化することを特徴とする。このよう
にエポキシ樹脂組成物からなる未硬化の成形材料と、Ｎ
ＢＲ組成物又は水素添加ＮＢＲ組成物からなる未加硫の
成形材料とを、それぞれ未硬化及び未加硫の状態で積層
加熱することにより、両者を強固に硬化接着一体化させ
ることができ、エポキシ樹脂組成物からなる成形材料、
例えばエポキシ樹脂組成物をマトリックス樹脂とする繊
維強化プラスチックスの優れた強度や剛性等の機械的性
質をＮＢＲ組成物又は水素添加ＮＢＲ組成物からなる成
形材料に付与し、しかも、軽量化することが可能であ
る。The method of the present invention for achieving such an object comprises an uncured material or an uncured molding material composed of an epoxy resin composition, and an NBR composition or a hydrogenated NBR composition. It is characterized in that an unvulcanized molding material is laminated and heated to be cured and bonded to be integrated. Thus, an uncured molding material composed of an epoxy resin composition and N
By stacking and heating an unvulcanized molding material composed of a BR composition or a hydrogenated NBR composition in an uncured and unvulcanized state, respectively, it is possible to firmly cure and bond both of them, and to obtain an epoxy resin. A molding material made of a resin composition,
For example, it is possible to impart mechanical properties such as excellent strength and rigidity of fiber-reinforced plastics using an epoxy resin composition as a matrix resin to a molding material composed of an NBR composition or a hydrogenated NBR composition, and to reduce the weight. It is possible.
【０００６】本発明に使用するエポキシ樹脂組成物は特
に限定されるものではないが、例えばビスフェノールＡ
型エポキシ樹脂１００重量部に対し両末端にカルボキシ
ル基を有する液状ブタジエン−アクリロニトリル共重合
体とグリシジルアミン型エポキシ樹脂との反応生成物１
０〜５０重量部、ニトリルゴム（ブタジエン−アクリロ
ニトリル共重合体ゴム）３〜８重量部、ジシアンアミド
等の硬化剤と硬化促進剤５〜１６重量部からなる組成物
が挙げられる。エポキシ樹脂は、ビスフェノールＡ型エ
ポキシ樹脂３０〜７０重量部と臭素化ビスフェノールＡ
型エポキシ樹脂の７０〜３０重量部の混合物であっても
よい。The epoxy resin composition used in the present invention is not particularly limited, but for example, bisphenol A is used.
Reaction product 1 of liquid butadiene-acrylonitrile copolymer having carboxyl groups at both ends and glycidyl amine type epoxy resin per 100 parts by weight of epoxy resin
The composition includes 0 to 50 parts by weight, 3 to 8 parts by weight of nitrile rubber (butadiene-acrylonitrile copolymer rubber), 5 to 16 parts by weight of a curing agent such as dicyanamide and a curing accelerator. The epoxy resin is 30 to 70 parts by weight of bisphenol A type epoxy resin and brominated bisphenol A.
It may be a mixture of 70 to 30 parts by weight of the type epoxy resin.
【０００７】このようなエポキシ樹脂組成物からなる未
硬化の成形材料は、前記組成物単独のみならず、このエ
ポキシ樹脂組成物をマトリックス樹脂とし、ガラス繊
維、炭素繊維、炭化ケイ素繊維、ボロン繊維、アラミド
繊維等の繊維を補強繊維とする繊維強化プラスチック
（プリプリグ）であってもよい。本発明に使用するＮＢ
Ｒ組成物としては、原料ゴム成分としてＮＢＲを少なく
とも５０重量％以上含有し、硫黄等の加硫剤、カーボン
ブラック等の補強剤、老化防止剤、加硫促進剤、その他
の各種ゴム薬品を、それぞれが所定量配合したものを使
用することができる。The uncured molding material composed of such an epoxy resin composition is not limited to the above composition alone, but this epoxy resin composition is used as a matrix resin, and glass fiber, carbon fiber, silicon carbide fiber, boron fiber, A fiber reinforced plastic (prepreg) having fibers such as aramid fibers as reinforcing fibers may be used. NB used in the present invention
The R composition contains at least 50% by weight or more of NBR as a raw rubber component, and contains a vulcanizing agent such as sulfur, a reinforcing agent such as carbon black, an antioxidant, a vulcanization accelerator, and other various rubber chemicals, Each of them can be used in a prescribed amount.
【０００８】また、本発明に使用する水素添加ＮＢＲ組
成物としては、エチレン性不飽和ニトリル単位を１０〜
６０重量部含有し、共役ジエン単位を３０重量部以下を
含有する水素添加ＮＢＲ１００重量部に対し、メタクリ
ル酸２０〜６０重量部、酸化亜鉛１０〜６０重量部で、
かつメタクリル酸と酸化亜鉛とのモル比が１／０．５〜
１／３の範囲であり、有機過酸化物を０．５〜２０重量
部配合したものがある。具体的には、日本ゼオン社から
製造販売されているＺＳＣ２２９５がある。The hydrogenated NBR composition used in the present invention contains 10 to 10 ethylenically unsaturated nitrile units.
60 parts by weight, with respect to 100 parts by weight of hydrogenated NBR containing 30 parts by weight or less of conjugated diene units, methacrylic acid 20 to 60 parts by weight, zinc oxide 10 to 60 parts by weight,
Moreover, the molar ratio of methacrylic acid and zinc oxide is 1 / 0.5 to
It is in the range of ⅓, and there is one containing 0.5 to 20 parts by weight of an organic peroxide. Specifically, there is ZSC2295 manufactured and sold by Nippon Zeon Co., Ltd.
【０００９】これらＮＢＲ組成物又は水素添加ＮＢＲ組
成物からなる未加硫の成形材料はスチールコードのよう
な金属コード、ナイロン、ポリエステル、アラミド等の
各種有機繊維からなるコードにより補強したものであっ
てもよい。これらエポキシ樹脂組成物からなる未硬化の
成形材料とＮＢＲ組成物又は水素添加ＮＢＲ組成物から
なる未加硫の成形材料とは、シート状又は板状にプレフ
ォームし、両者を重ね合わせて加熱することにより接着
複合体にすることができる。The unvulcanized molding material comprising these NBR composition or hydrogenated NBR composition is reinforced by metal cords such as steel cords, cords made of various organic fibers such as nylon, polyester and aramid. Good. The uncured molding material composed of these epoxy resin compositions and the unvulcanized molding material composed of the NBR composition or the hydrogenated NBR composition are preformed into a sheet or plate, and both are superposed and heated. By doing so, an adhesive composite can be obtained.
【００１０】これらエポキシ樹脂組成物とＮＢＲ組成物
又は水素添加ＮＢＲ組成物は、前者が未硬化、後者が未
加硫であることが必要である。エポキシ樹脂組成物が硬
化していたり、ＮＢＲ組成物又は水素添加ＮＢＲ組成物
が加硫されていたりすると、両者を接着させることがで
きない。積層後の加熱条件としては、エポキシ樹脂組成
物からなる未硬化の成形材料の硬化とＮＢＲ組成物又は
水素添加ＮＢＲ組成物からなる未加硫の成形材料の加硫
とを同時に進行完結させる条件であれば、特に限定され
るものではないが、好ましくは５〜４０ｋｇｆ／ｃｍ2
の加圧下に１２０〜２２０℃の温度の条件にするのがよ
い。In the epoxy resin composition and NBR composition or hydrogenated NBR composition, it is necessary that the former is uncured and the latter is unvulcanized. If the epoxy resin composition is cured or the NBR composition or hydrogenated NBR composition is vulcanized, they cannot be bonded to each other. The heating conditions after lamination are such that curing of an uncured molding material composed of an epoxy resin composition and vulcanization of an unvulcanized molding material composed of an NBR composition or a hydrogenated NBR composition are simultaneously completed. If it exists, it is not particularly limited, but preferably 5 to 40 kgf / cm 2.
It is preferable to set the temperature of 120 to 220 ° C. under the pressure.
【００１１】[0011]
【実施例】表１に示す配合組成を有するＮＢＲ、天然ゴ
ム（ＮＲ）、エチレン−プロピレン−ジエン共重合体ゴ
ム（ＥＰＤＭ）、スチレン−ブタジエン共重合体ゴム
（ＳＢＲ）及びイソブチレン−イソプレン共重合体ゴム
（ＩＩＲ）の５種類のゴム組成物１〜５を調製した。こ
れら各ゴム組成物１〜５を用いて、それぞれ１５０ｍｍ
×５０ｍｍ×０．０５ｍｍの未加硫のシート材料に成形
した。EXAMPLES NBR, natural rubber (NR), ethylene-propylene-diene copolymer rubber (EPDM), styrene-butadiene copolymer rubber (SBR), and isobutylene-isoprene copolymer having the compounding composition shown in Table 1. Five kinds of rubber compositions 1 to 5 of rubber (IIR) were prepared. Using each of these rubber compositions 1 to 5, 150 mm
It was molded into an unvulcanized sheet material of x50 mm x 0.05 mm.
【００１２】次に、日本ゼオン社製の水素添加ＮＢＲ組
成物、ＺＳＣ２２９５，８５重量％に、日本ゼオン社製
の水素添加ＮＢＲのＺＥＴＰＯＬ２０２０，１５重量％
をロールで添加し、その混合物１００重量部に老化防止
剤（ナウガード４４５）１．５重量部、有機過酸化物の
１，３−ビスターシャリーブチルパーオキシ−イソプロ
ピルベンゼン（化薬アクゾ社製パーカドックス１４／４
０“）５重量部をロールで添加したものを使用した。こ
れを１５０ｍｍ×５０ｍｍ×２．５ｍｍのシート状材料
に成形した。Next, the hydrogenated NBR composition made by Nippon Zeon Co., Ltd., ZSC2295, 85% by weight, and the hydrogenated NBR ZETPOL 2020, 15% by weight made by Nippon Zeon Co., Ltd.
Is added by a roll, and 1.5 parts by weight of an antioxidant (Nowguard 445) is added to 100 parts by weight of the mixture, 1,3-bister-shearyl butylperoxy-isopropylbenzene as an organic peroxide (Perkadox manufactured by Kayaku Akzo Co., Ltd. 14/4
A roll of 5 parts by weight of 0 "was used. This was molded into a sheet material having a size of 150 mm x 50 mm x 2.5 mm.
【００１３】他方、エポキシ樹脂組成物としては、シェ
ル化学社製のビスフェノールＡ型エポキシ樹脂のエピコ
ート８２８，５００ｇ、ダウケミカル社製の臭素化ビス
フェノールＡ型エポキシ樹脂ＤＥＲ５１１，５００ｇ、
両末端にカルボキシル基を有するブタジエン−アクリロ
ニトリル共重合体とグリシジルアミン型エポキシ樹脂と
の反応生成物〔この反応生成物はＢ．Ｆ．グッドリッチ
社製のハイカーＣＴＢＮ，１３００×１３，１５０ｇと
チバガイギー社製のエポキシ樹脂アラルダイトＭＹ７２
０、１００ｇとからなる混合物に、トリフェニルホスフ
ィン０．４ｇを添加し、１７０℃で１時間反応させたも
の〕，１５０ｇ、日本ゼオン社製のニトリルゴムのニポ
ール１０７２，５０ｇ、硬化剤のジシアンアミド（ＤＩ
ＣＹ）４０ｇ、硬化促進剤の３−（３，４−ジクロルフ
ェノール）−１，１’−ジメチル尿素（ＤＭＵ）５０ｇ
を加えたものを使用した。このエポキシ樹脂組成物は、
アセトンとセロソルブとの混合溶剤に溶解し、５０重量
％の濃度の溶液とした。この溶液を炭素繊維の平織クロ
スに２００ｇ／ｍ2 の量含浸させた後、１時間乾燥して
樹脂含有量４２体積％のプリプリグを作製し、１５０ｍ
ｍ×５０ｍｍ×０．０５ｍｍの大きさの未硬化のシート
材料に成形した。On the other hand, as the epoxy resin composition, Epicoat 828,500 g of bisphenol A type epoxy resin manufactured by Shell Chemical Co., Ltd., brominated bisphenol A type epoxy resin DER 511,500 g manufactured by Dow Chemical Company,
A reaction product of a butadiene-acrylonitrile copolymer having a carboxyl group at both ends and a glycidyl amine type epoxy resin (this reaction product is described in B.I. F. Goodrich hiker CTBN, 1300 x 13,150g and Ciba Geigy epoxy resin Araldite MY72
0.4 g of triphenylphosphine was added to a mixture of 0 and 100 g and reacted at 170 ° C. for 1 hour], 150 g, Nipol 1072, 50 g of nitrile rubber manufactured by Zeon Corporation, and dicyanamide (a curing agent). DI
CY) 40 g, curing accelerator 3- (3,4-dichlorophenol) -1,1′-dimethylurea (DMU) 50 g
Was used. This epoxy resin composition,
It was dissolved in a mixed solvent of acetone and cellosolve to obtain a solution having a concentration of 50% by weight. A plain woven cloth of carbon fibers was impregnated with this solution in an amount of 200 g / m 2 and then dried for 1 hour to prepare a prepreg having a resin content of 42% by volume.
It was formed into an uncured sheet material having a size of m × 50 mm × 0.05 mm.
【００１４】これらゴム組成物１〜５及び水素添加ＮＢ
Ｒ組成物からなる未硬化のシート材料に、それぞれ未硬
化エポキシ樹脂組成物をマトリックスとした平織カーボ
ンクロス含浸物（プリプレグ）のシート材料を重ね合わ
せて２０ｋｇ／ｃｍ2 の化圧下、１７０℃で２０分間加
熱し、ゴム組成物１〜５及び水素添加ＮＢＲ組成物を加
硫すると同時に前記エポキシ樹脂組成物からなる未硬化
のシート材料を硬化させた。These rubber compositions 1 to 5 and hydrogenated NB
The sheet material of the plain weave carbon cloth impregnated material (prepreg) using the uncured epoxy resin composition as a matrix is overlaid on the uncured sheet material of the R composition, and the sheet material is heated at 170 ° C. under a pressure of 20 kg / cm 2. The rubber compositions 1 to 5 and the hydrogenated NBR composition were vulcanized by heating for minutes, and at the same time, the uncured sheet material composed of the epoxy resin composition was cured.
【００１５】 表１中の数値は、いずれも重量部である。[0015] All the numerical values in Table 1 are parts by weight.
【００１６】また、＊1 はＮ−フェニル−Ｎ’−イソプ
ロピル−ｐ−フェニレンジアミン ＊2 はＮ−ｔ−ブチル−２−ベンゾチアゾールスルフェ
ンアミド ＊3 はテトラメチルチウラムジスルフィド ＊4 は２−メルカプトベンゾチアゾール ＊5 はテトラメチルチウラムモノスルフィド ＊6 はベンゾチアジルジスルフィドである。* 1 is N-phenyl-N'-isopropyl-p-phenylenediamine * 2 is Nt-butyl-2-benzothiazolesulfenamide * 3 is tetramethylthiuram disulfide * 4 is 2-mercapto Benzothiazole * 5 is tetramethyl thiuram monosulfide * 6 is benzothiazyl disulfide.
【００１７】表１のゴム組成物１〜５及び前述の水素添
加ＮＢＲ組成物からなる未加硫のゴムシート材料に対
し、それぞれ前記エポキシ樹脂組成物をマトリックスと
して含浸した平織カーボン繊維クロス（プリプレグ）と
重ね合わせて２０ｋｇ／ｃｍ2の加圧下、１２０℃で２
０分間加熱し、ゴム組成物１〜５及び水素添加ＮＢＲ組
成物からなるシート材料を加硫すると同時に前記エポキ
シ樹脂組成物からなる未硬化のシート材料を硬化させ
た。A plain weave carbon fiber cloth (prepreg) obtained by impregnating an unvulcanized rubber sheet material composed of the rubber compositions 1 to 5 in Table 1 and the above-mentioned hydrogenated NBR composition with the epoxy resin composition as a matrix. 2 at 120 ° C under pressure of 20 kg / cm 2
By heating for 0 minutes, the sheet material composed of the rubber compositions 1 to 5 and the hydrogenated NBR composition was vulcanized, and at the same time, the uncured sheet material composed of the epoxy resin composition was cured.
【００１８】その結果、ゴム組成物１のＮＢＲ組成物と
水素添加ＮＢＲ組成物からなるシート材料は、平織カー
ボン繊維クロスと強固に接着したが、他の４種類のゴム
組成物２〜５からなるシート材料は、いずれも接着しな
かった。同様に、表１に示すゴム組成物と水素添加ＮＢ
Ｒ組成物からなる未加硫のゴムシート材料の間に、未硬
化のエポキシ樹脂組成物を塗布して、前記と同一条件下
に加熱し、加硫硬化させた。その結果、ＮＢＲ組成物と
水素添加ＮＢＲ組成物からなるシート材料は強固に接着
したが、他の４種類のゴム組成物２〜５からなるシート
材料は、いずれも接着しなかった。As a result, the sheet material composed of the NBR composition and the hydrogenated NBR composition of the rubber composition 1 firmly adhered to the plain weave carbon fiber cloth, but consisted of the other 4 kinds of rubber compositions 2 to 5. None of the sheet materials adhered. Similarly, the rubber composition shown in Table 1 and hydrogenated NB
An uncured epoxy resin composition was applied between unvulcanized rubber sheet materials made of the R composition, and heated and vulcanized and cured under the same conditions as above. As a result, the sheet materials composed of the NBR composition and the hydrogenated NBR composition adhered firmly, but the sheet materials composed of the other four rubber compositions 2 to 5 did not adhere to each other.
【００１９】[0019]
【発明の効果】本発明によれば、エポキシ樹脂組成物か
らなる未硬化の成形材料とＮＢＲ組成物又は水素添加Ｎ
ＢＲ組成物からなる未加硫の成形材料とを積層加熱する
ことにより、両者を接着一体化することができ、優れた
強度や剛性等の機械的性質を有し、軽量化可能な接着複
合体を製造することができる。According to the present invention, an uncured molding material composed of an epoxy resin composition and an NBR composition or hydrogenated N are used.
By laminating and heating an unvulcanized molding material composed of a BR composition, the both can be bonded and integrated, have excellent mechanical properties such as strength and rigidity, and can be reduced in weight. Can be manufactured.
フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｂ２９Ｋ 55:00 63:00 Ｂ２９Ｌ 9:00 4Ｆ Continuation of the front page (51) Int.Cl. 5 Identification number Office reference number FI technical display location // B29K 55:00 63:00 B29L 9:00 4F
Claims (1)
形材料と、アクリロニトリル−ブタジエン共重合体含有
ゴム組成物からなる未加硫の成形材料又は水素添加アク
リロニトリル−ブタジエン共重合体ゴム、メタクリル
酸、酸化亜鉛及び有機過酸化物を含有するゴム組成物か
らなる未加硫の成形材料とを積層し、加熱下に硬化接着
一体化する熱硬化性樹脂とゴムとの接着複合体の製造方
法。1. An uncured molding material composed of an epoxy resin composition, and an unvulcanized molding material composed of a rubber composition containing an acrylonitrile-butadiene copolymer, or hydrogenated acrylonitrile-butadiene copolymer rubber, methacrylic acid, A method for producing an adhesive composite of a thermosetting resin and rubber, which comprises laminating an unvulcanized molding material composed of a rubber composition containing zinc oxide and an organic peroxide, and curing and adhering the same under heating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10755992A JPH05301972A (en) | 1992-04-27 | 1992-04-27 | Production of bonded composite body of thermosetting resin and rubber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10755992A JPH05301972A (en) | 1992-04-27 | 1992-04-27 | Production of bonded composite body of thermosetting resin and rubber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05301972A true JPH05301972A (en) | 1993-11-16 |
Family
ID=14462251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10755992A Pending JPH05301972A (en) | 1992-04-27 | 1992-04-27 | Production of bonded composite body of thermosetting resin and rubber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05301972A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1063255A1 (en) * | 1998-04-30 | 2000-12-27 | TOKYO R & D Co., Ltd. | Fiber reinforced composite material based on thermohardened resin and vulcanized rubber |
| KR102184814B1 (en) * | 2019-05-23 | 2020-11-30 | 재단법인 한국탄소융합기술원 | Epoxy resin composition having improved adhesion and fiber-rubber composite connecting material using the same |
-
1992
- 1992-04-27 JP JP10755992A patent/JPH05301972A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1063255A1 (en) * | 1998-04-30 | 2000-12-27 | TOKYO R & D Co., Ltd. | Fiber reinforced composite material based on thermohardened resin and vulcanized rubber |
| US6258422B1 (en) | 1998-04-30 | 2001-07-10 | Tokyo R&D Co., Ltd. | Molding method for thermosetting resin based, rubber vulcanization type, fiber reinforced composite material, and thermosetting resin, based, rubber vulcanization type, fiber reinforced composite material |
| KR102184814B1 (en) * | 2019-05-23 | 2020-11-30 | 재단법인 한국탄소융합기술원 | Epoxy resin composition having improved adhesion and fiber-rubber composite connecting material using the same |
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