US4482703A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermosetting resin composition comprising dicyanamide and polyvalent imide

Assignee: Hitachi Ltd

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Filing: 1982-10-20

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Granted: 1984-11-13

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Expires: 2002-10-20

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Abstract

Abstract A thermosetting resin composition comprises (A) at least one dicyanamide compound and (B) at least one polyvalent imide having one or more unsaturated bonds and, if necessary (C) at least one polymerizable compound of epoxy compounds, phenolic compounds and triallyl isocyanurate compounds. A thermosetting prepolymer can be obtained by subjecting the composition to a preliminary reaction with heating to the B stage and this prepolymer can give a cured product having excellent heat resistance of class C and flexibility. An exemplary composition containing 60 parts by wt. of 4,4'-dicyanomidodiphenylmethane and 40 parts by wt. of N,N'-4,4'-diphenylmethane bismaleimide dissolved in methyl Cellosolve is reacted at 70 DEG to 110 DEG C. for about 40 minutes to obtain a prepolymer soluble in methyl ethyl ketone. This prepolymer when admixed with 2-ethyl-4-methyl-imidazole and after removal of the methyl cellusolve will form an insoluble and infusible cured product upon heating at temperatures on the order of 170 DEG to 200 DEG C. for about 80 minutes. The resin composition when admixed with a solvent, is useful for impregnation and when used as a powder, it is useful as a molding resin.

Inventors

👤 Akio Takahashi
👤 Takeshi Shimazaki
👤 Motoyo Wajima
👤 Hirosada Morishita

Bibliographic Details

Application Number —

Jurisdiction US

Data Source google_patents

Last Synchronized 2026-10-29 19:50

CPC Classifications

C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12

Claims Analysis

Total Claims: 11

Claim 1

Independent Claim 41 words

A thermosetting resin composition comprising (A) at least one dicyanamide compound represented by the formula: NCHN--Y--NHCN (I) wherein Y is a divalent organic group having an aromatic ring, and (B) at least one polyvalent imide having at least two maleimide rings.

Claim 2

Dependent Claim 41 words

Claim 3

Dependent Claim 45 words

A thermosetting prepolymer obtained by reacting a composition comprising (A) at least one dicyanamide compound represented by the formula: NCHN--Y--NHCN (I) wherein Y is a divalent organic group having an aromatic ring, and (B) at least one polyvalent imide having at least two maleimide rings.

Claim 4

Dependent Claim 45 words

Claim 5

Dependent Claim 62 words

Claim 6

Dependent Claim 62 words

Claim 7

Dependent Claim 76 words

A composition according to claim 3, wherein said dicyanamide compound is selected from the group consisting of 4,4'-dicyanamidodicyclohexylmethane, 1,4-dicyanamidocyclohexane, 2,6-dicyanamidopyridine, m-phenylene dicyanamide, p-phenylene dicyanamide, 4,4'-dicyanamidodiphenylmethane, 2,2'-bis(4-cyanamidophenyl)propane, 4,4'-dicyanamidophenyloxide, 4,4'-dicyanamidodiphenylsulfone, bis(4-cyanamidophenyl)phosphine oxide, bis(4-cyanamidophenyl)-phenylphosphine oxide, bis(4-cyanamidophenyl)methylamine, 1,5-dicyanamidonaphthalene, m-xylylene dicyanamide, p-xylene dicyanamide, hexamethylene dicyanamide, 6,6'-dicyanamide-2,2'-dipyridyl, 4,4'-dicyanamidobenzophenone, 4,4'-dicyanamidoazobenzene, bis(4-cyanamidophenyl)phenylmethane, 1,1-bis(4-cyanamidophenyl)cyclohexane, 1,1-bis(4-cyanamido-3-methylphenyl)-1,3,4-oxadiazol, 4,4'-dicyanamidodiphenylether, 4,4'-bis(p-cyanamidophenyl)-2,2'-dithiazol, m-bis(4-p-cyanamidophenyl-2-thiazolyl)benzene, 4,4'-dicyanamidobenzanilide, 4,4'-dicyanamidophenyl benzoate, 2,2'-bis[4-(4-cyanamidophenoxy)-phenyl]propane, 2,2'-bis[3-methyl-4-(4-cyanamidophenoxy)phenyl]propane, 2,2-bis[3-ethyl-4-(4-cyanamidophenoxy)phenyl]propane, 2,2-bis[3-propyl-4-(4-cyanamideophenoxy)phenyl]propane, 2,2-bis[3-isopropyl-4-(4-cyanamidophenoxy)phenyl]propane, bis[4-(4-cyanamidophenoxy)phenyl]methane, and a cyanamide-terminated sulfone ether oligomer represented by the following formula: ##STR5## wherein n is zero to 3.

Claim 8

Dependent Claim 61 words

A composition according to claim 4, wherein the polyvalent imide is selected from the group consisting of N,N'-methylene bismaleimide, N,N'ethylene bismaleimide, N,N'-hexamethylene bismaleimide, N,N'-trimethylene bismaleimide, N,N'-m-phenylene bismaleimide, N,N'-p-phenylene bismaleimide, N,N'-4,4'-diphenylmethane bismaleimide, N,N'-4,4'-diphenylether bismaleimide, N,N'-methylene bis(3-chloro-p-phenylene)bismaleimide, N,N'-4,4'-diphenylsulfone bismaleimide, N,N'-4,4'-dicyclohexylmethane bismaleimide, N,N'-α,α'-4,4'-dimethylene cyclohexane bismaleimide, N,N'-m-xylene bismaleimide, N,N'-4,4'-diphenylcyclohexane bismaleimide and a polyimide represented by the following formula: ##STR6## wherein m is zero to 3.

Claim 9

Dependent Claim 62 words

A cured product having structural units of the formula: ##STR7## wherein Y is a divalent organic group having an aromatic ring, R 1 and R 2 are independently hydrogen, an alkyl group or a halogen atom, and of the formula: ##STR8## wherein R 2 is a hydrogen, an alkyl group or a halogen atom and Y has the same meaning as above.

Claim 10

Dependent Claim 62 words

Claim 11

Dependent Claim 16 words

A cured product according to claim 6, wherein R 1 in the formula (II) is hydrogen.

References Cited (Backward Citations)

GB1322332A Cited

US3770705A Cited

US4043986A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1987-11-13	1988-05-14	1988-11-13	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1991-11-13	1992-05-14	1992-11-13	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1995-11-13	1996-05-14	1996-11-13	$7700.00	Window Closed / Lapsed

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