Heat-Resistant Adhesive Composition from a Bis-Maleimide, an Alpha-Cyanoacrylate and Optionally a Diamine

United States Patent [191 Akiyama et al. [54] HEAT-RESISTANT ADHESIVE COMPOSITION FROM A BIS-MALEIMIDE, AN ALPHA-CYANOACRYLATE AND OPTIONALLY A DIAMINE [75] Inventors: Keiiti Akiyama, Yokosuka; Shyuichi Suzuki; Yukihiro Mikogami, both of ‘ Yokohama, all of Japan [73] Assignee: Tokyo Shibaura Electric Co., Ltd., Kawasaki, Japan [22] Filed: Apr. 1, 1974 [21] Appl. No.: 456,609 [30] Foreign Application Priority Data Apr. 24, 1973 Japan . . . . . . . . . . . . . . . . . . . . . . .. 48-45717 Aug. 6, 1973 Japan . . . . . . . . . . . . . . . .. 48~87620 Sept. 27, 1973 Japan ............................ .. 48-107993 [52] U.S. Cl. .. 260/47 UA; 260/30.4 R; 260/31.4 R; 260/32.8 N; 260/47 CZ; 260/63 N; 260/65; 260/78 UA; 428/474 01 O O [0 O O LAP-SHEAR TENSILE BREAK DOWN LOAD (Kg) 6 00 O 100 [11] 3,928,286 [45] Dec. 23, 1975 [51] Int. cm ........................................ .. cosc 69/26 [58] Field of Search ..... .. 260/78 UA, 47 C2, 47 UA [56] References Cited UNITED STATES PATENTS 6/I973 Schroeter ..................... ..260/78 UA 9/1973 Witzel .......................... ..260/78 UA 3,742,089 3,761,430 Primary Examiner—Harold D. Anderson Attorney, Agent, or Firm—Kemon, Palmer & Estabrook [57] ABSTRACT A heat-resistant adhesive composition including 85 to 1 mol% of N,N’-substituted bismaleimide and 15 to 99 mol% of oz-cyanoacrylate. Diamines or silane coupling agents may be incorporated. ‘I 7 Claims, 2 Drawing Figures ‘ 250 200 TEMPERATURE (°C) ——" 3,928,286 US. Patent Dec. 23, 1975 i Fl G. 300 « 250 260 +60 TEMPERATURE (°C) 0 0 O O O 2 . III .9; 96.. 2300 v_