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US4283522A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing thermosetting prepolymer from mixture of polyfunctional maleimide and bis-maleimide

Assignee: Resonac Corp
•
Filing: 1979-08-31
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Granted: 1981-08-11
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Expires: 1999-08-31
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Abstract

Abstract A process for preparing a thermosetting maleimide type prepolymer which comprises heating (A) a polyfunctional maleimide compound derived from a polyamine prepared from aniline and formalin, (B) a bis-maleimide and (C) a diamine. The thermosetting maleimide type prepolymer prepared according to the process of the present invention is excellent in solubility in low boiling point solvents such as acetone, methyl ethyl ketone and methyl cellosolve, which are available at low cost. Accordingly, the prepolymer is advantageously used especially for the production of laminated boards having excellent heat resisting properties.

Inventors

  • 👤 Akio Takahashi
  • 👤 Yutaka Itoh
  • 👤 Motoyo Wajima
  • 👤 Hirosada Morishita
  • 👤 Kenji Tsukanishi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 21:01
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/121

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 192 words
A process for preparing a thermosetting maleimide prepolymer, which comprises heating, at a temperature of 100° to 150° C. for 10 to 60 minutes, (A) a polyfunctional maleimide compound obtained by the dehydration reaction of an amide acid formed from maleic anhydride and a polyamine prepared by the condensation of aniline with formaldehyde and represented by the formula (1): ##STR12## wherein n is in the range of from 0.1 to 3.0; (B) a bis-maleimide selected from the group consisting of N,N'-4,4'-diphenylmethane-bis-maleimide, N,N'-methylenebis-(3-chloro-p-phenylene)-bis-maleimide, N,N'-4,4'-diphenyl-sulfone-bis-maleimide, N,N'-4,4'-diphenyl-ether-bis-maleimide, N,N'-ethylene-bis-maleimide, N,N'-hexamethylene-bis-maleimide and combinations thereof; and (C) a diamine selected from the group consisting of 4,4'-diaminodicyclohexylmethane, 1,4-diaminocyclohexane, 2,6-diaminopyridine, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 2,2'-bis(4-aminophenyl)propane, benzidine, 4,4'-diaminodiphenylsulfone, bis(4-aminophenyl) methylphosphine oxide, bis(4-aminophenyl)phenylphosphine oxide, bis(4-aminophenyl)methylamine, 1,5-diaminonaphthalene, m-xylylenediamine, p-xylylenediamine, hexamethylenediamine, 6,6'-diamino-2,2'-dipyridyl, 4,4'-diaminobenzophenone, 4,4'-diaminoazobenzene, bis(4-aminophenyl)phenylmethane, 1,1-bis(4-aminophenyl)cyclohexane, 1,1-bis(4-amino-3-methylphenyl)cyclohexane, 2,5-bis(m-aminophenyl)-1,3,4-oxadiazole, 2,5-bis(p-aminophenyl)-1,3,4-oxadiazole, 2,5-bis(m-aminophenyl)thialoro(4,5-d)thiazole, 5,5'-di(m-aminophenyl)-2,2'-bis(1,3,4-oxadiazolyl), 4,4'-diaminodiphenyl ether, 4,4'-bis(p-aminophenyl)-2,2'-dithiazole, m-bis(4-p-aminophenyl-2-thiazolyl)benzene, 4,4'-diaminobenzanilide, 4,4'-diaminophenyl benzoate, N,N'-bis(4-aminobenzyl)-p-phenylenediamine, 4,4'-methylenebis(2-chloroaniline) and combinations thereof; the weight proportion of the polyfunctional maleimide compound (A) relative to the total of the polyfunctional maleimide compound (A) and the bis-maleimide (B) being 10 to 80% and the molar ratio of the total of the polyfunctional maleimide compound (A) and the bis-maleimide (B) to the diamine (C) being 1:1 to 1:0.3.
Claim 2
Dependent Claim 192 words
A process for preparing a thermosetting maleimide prepolymer, which comprises heating, at a temperature of 100° to 150° C. for 10 to 60 minutes, (A) a polyfunctional maleimide compound obtained by the dehydration reaction of an amide acid formed from maleic anhydride and a polyamine prepared by the condensation of aniline with formaldehyde and represented by the formula (1): ##STR12## wherein n is in the range of from 0.1 to 3.0; (B) a bis-maleimide selected from the group consisting of N,N'-4,4'-diphenylmethane-bis-maleimide, N,N'-methylenebis-(3-chloro-p-phenylene)-bis-maleimide, N,N'-4,4'-diphenyl-sulfone-bis-maleimide, N,N'-4,4'-diphenyl-ether-bis-maleimide, N,N'-ethylene-bis-maleimide, N,N'-hexamethylene-bis-maleimide and combinations thereof; and (C) a diamine selected from the group consisting of 4,4'-diaminodicyclohexylmethane, 1,4-diaminocyclohexane, 2,6-diaminopyridine, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 2,2'-bis(4-aminophenyl)propane, benzidine, 4,4'-diaminodiphenylsulfone, bis(4-aminophenyl) methylphosphine oxide, bis(4-aminophenyl)phenylphosphine oxide, bis(4-aminophenyl)methylamine, 1,5-diaminonaphthalene, m-xylylenediamine, p-xylylenediamine, hexamethylenediamine, 6,6'-diamino-2,2'-dipyridyl, 4,4'-diaminobenzophenone, 4,4'-diaminoazobenzene, bis(4-aminophenyl)phenylmethane, 1,1-bis(4-aminophenyl)cyclohexane, 1,1-bis(4-amino-3-methylphenyl)cyclohexane, 2,5-bis(m-aminophenyl)-1,3,4-oxadiazole, 2,5-bis(p-aminophenyl)-1,3,4-oxadiazole, 2,5-bis(m-aminophenyl)thialoro(4,5-d)thiazole, 5,5'-di(m-aminophenyl)-2,2'-bis(1,3,4-oxadiazolyl), 4,4'-diaminodiphenyl ether, 4,4'-bis(p-aminophenyl)-2,2'-dithiazole, m-bis(4-p-aminophenyl-2-thiazolyl)benzene, 4,4'-diaminobenzanilide, 4,4'-diaminophenyl benzoate, N,N'-bis(4-aminobenzyl)-p-phenylenediamine, 4,4'-methylenebis(2-chloroaniline) and combinations thereof; the weight proportion of the polyfunctional maleimide compound (A) relative to the total of the polyfunctional maleimide compound (A) and the bis-maleimide (B) being 10 to 80% and the molar ratio of the total of the polyfunctional maleimide compound (A) and the bis-maleimide (B) to the diamine (C) being 1:1 to 1:0.3.
Claim 3
Dependent Claim 30 words
A process according to claim 1, wherein said diamine is m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 2,2'-bis(4-aminophenyl)propane, 4,4'-diaminodiphenylsulfone, bis(4-aminophenyl)methylphosphine oxide, bis(4-aminophenyl)phenylphosphine oxide, bis(4-aminophenyl)-methylamine, p-xylylenediamine, hexamethylenediamine, bis(4-aminophenyl)phenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-methylenebis(2-chloroaniline) or a combination thereof.
Claim 4
Dependent Claim 27 words
A process according to claim 1 or 2, wherein the heating is effected in the dissolved state of the materials (A), (B) and (C) in a solvent.
Claim 5
Dependent Claim 15 words
A process according to claim 3, wherein said solvent is 2-methoxyethanol, 2-ethoxyethanol, 2-(methoxymethoxy)ethanol or 2-isopropoxyethanol.
Claim 6
Dependent Claim 12 words
A thermosetting maleimide prepolymer produced by a process according to claim 1.
Claim 7
Dependent Claim 24 words
A thermosetting maleimide prepolymer produced by a process according to claim 1, wherein the bis-maleimide (B) is N,N'-4,4'-diphenylmethane-bis-maleimide and the diamine (C) is 4,4'-diaminodiphenylmethane.
Claim 8
Dependent Claim 24 words
A thermosetting maleimide prepolymer produced by a process according to claim 1, wherein the bis-maleimide (B) is N,N'-4,4'-diphenylmethane-bis-maleimide and the diamine (C) is 4,4'-methylene-bis-(2-chloroaniline).
Claim 9
Dependent Claim 24 words
A thermosetting maleimide prepolymer produced by a process according to claim 1, wherein the bis-maleimide (B) is N,N'-methylene-bis-(3-chloro-p-phenylene)-bis-maleimide and the diamine (C) is 4,4'-diaminodiphenylmethane.
Claim 10
Dependent Claim 24 words
A thermosetting maleimide prepolymer produced by a process according to claim 1, wherein the bis-maleimide (B) is N,N-4,4'-diphenyl-ether-bis-maleimide and the diamine (C) is 4,4'-diaminodiphenylmethane.
Claim 11
Dependent Claim 24 words
A thermosetting maleimide prepolymer produced by a process according to claim 1, wherein the bis-maleimide (B) is N,N'-4,4'-diphenyl-ether-bis-maleimide and the diamine (C) is hexamethylenediamine.

References Cited (Backward Citations)

US3562223A Cited
US3658764A Cited
US3883486A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-08-10 1985-02-09 1985-08-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-08-10 1989-02-09 1989-08-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-08-10 1993-02-09 1993-08-11 $7700.00 Window Closed / Lapsed

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