# US 5,350,635 A · Cyanate resin adhesive for polyimide film > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,350,635 A - Document ID: US5350635A - Status: Granted - Kind: A - Application number: 07/994,693 - Filed: 1992-12-22 - Granted: 1994-09-27 - Earliest claimed: 1992-12-22 - Assignees: Minnesota Mining and Manufacturing Company - Inventors: Richard J. Pokorny - Web page: https://patentgrep.com/patent/US5350635A ## CPC - C08L 71/02: Polyalkylene oxides - C08G 59/4014: {Nitrogen containing compounds} - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors - C09J 179/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors - Y10T 428/31515: As intermediate layer - Y10T 428/31721: Of polyimide - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract Improvement in adhesion of cyanate resin adhesives by the addition of an epoxy resin. Polyether polyols may optionally be added to toughen the composition. ## Claims ### Claim 1 A method of improving the adhesion of cyanate resin to polyimide film comprising admixing an epoxy resin selected from the group consisting of methyl, ethyl hydantoin diepoxide, N,N,N', N'-tetraglycidyl-4,4'-methylenebisbenzenamine, diglycidyl ether of para-aminophenol, and mixtures thereof, with said cyanate resin in an amount of at least about 2.5 percent by weight based on the total weight of cyanate resin and epoxy resin. ### Claim 2 (depends on 1) A method according to claim 1 wherein said method further includes admixing a polyether polyol with said cyanate resin and epoxy resin, said polyether polyol being present in an amount of about 10 percent to about 30 percent by weight, based on the total weight of cyanate resin and polyether polyol. ### Claim 3 (depends on 1, 2) A method according to claim 1 or 2 wherein an amount of catalyst effective to promote the reaction of said resins is included in said admixture. ### Claim 4 (depends on 3) A method according to claim 3 wherein said catalyst is cobalt (III) acetyl acetonate. ### Claim 5 (depends on 1, 2) A method according to claim 1 or 2 wherein said admixture is reacted to form an at least partially polymerized composition. ### Claim 6 (depends on 5) The reaction product produced by the method of claim 5. ### Claim 7 (depends on 1, 2) A method according to claim 1 or 2 wherein said cyanate resin is an oligomer of a dicyanate monomer. ### Claim 8 (depends on 7) A method according to claim 7 wherein said dicyanate monomer is bis(4-cyanato-3,5 dimethylphenyl) methane. ### Claim 9 (depends on 2) A method according to claim 2 wherein said polyether polyol has a molecular weight of between about 400 and 1000. ### Claim 10 (depends on 9) A method according to claim 9 wherein said polyol is poly(tetramethylene ether) glycol. ### Claim 11 An article comprising a first polyimide substrate adhered to a second polyimide polymer substrate by an interposed adhesive layer, said adhesive layer comprising: a reaction product of an admixture of a cyanate resin and an epoxy resin, said epoxy resin being present in an amount of at least about 5 percent by weight based on the total weight of the cyanate resin and epoxy resin wherein said epoxy resin is selected from the group consisting of methyl, ethyl hydantoin diepoxide, N,N,N', N'-tetraglycidyl-4,4'-methylenebisbenzenamine, diglycidyl ether of para-aminophenol, and mixtures thereof. ### Claim 12 (depends on 11) An article according to claim 11 wherein said admixture further includes a polyether polyol, said polyether polyol being present in said admixture in an amount of about 10 percent to about 30% by weight, based on the total weight of cyanate resin and polyether polyol. ### Claim 13 (depends on 11, 12) An article according to claim 11 or 12 wherein an amount of catalyst effective to promote the reaction of said resins is included in said admixture. ### Claim 14 (depends on 13) An article according to claim 13 wherein said catalyst is cobalt (III) acetyl acetonate. ### Claim 15 (depends on 11, 12) An article according to claim 11 or 12 wherein said cyanate resin is an oligomer of a dicyanate monomer. ### Claim 16 (depends on 15) An article according to claim 15 wherein said dicyanate monomer is bis(4-cyanato-3,5 dimethylphenyl) methane. ### Claim 17 (depends on 12) An article according to claim 12 wherein said polyether polyol has a molecular weight of between about 400 and 1000. ### Claim 18 (depends on 17) An article according to claim 17 wherein said polyol is poly(tetramethylene ether) glycol. ### Claim 19 A composition for forming an adhesive polymer comprising a cyanate resin, an epoxy resin in an amount of at least 5 percent by weight based on the total weight of epoxy resin and cyanate resin, and a polyether polyol in an amount of about 10 percent to 30 percent by weight based on the total weight of cyanate resin and polyether polyol wherein said epoxy resin is selected from the group consisting of methyl, ethyl hydantoin diepoxide, N,N,N', N'-tetraglycidyl-4,4'-methylenebisbenzenamine, diglycidyl ether of para-aminophenol, and mixtures thereof. ### Claim 20 (depends on 19) A composition according to claim 19 which further includes a catalyst in an amount effective to promote the reaction of said components. ### Claim 21 (depends on 20) A composition according to claim 20 wherein said catalyst is cobalt (III) acetyl acetonate. ### Claim 22 (depends on 19) A composition according to claim 19 wherein said cyanate resin is an oligomer of a dicyanate monomer. ### Claim 23 (depends on 19) A composition according to claim 19 wherein said dicyanate monomer is bis(4-cyanato-3,5 dimethylphenyl) methane. ### Claim 24 (depends on 19) A composition according to claim 19 wherein said polyether polyol has a molecular weight of between about 400 and 1000. ### Claim 25 (depends on 24) A composition according to claim 24 wherein said polyol is poly(tetramethylene ether) glycol.