Patent US4097545A successfully refreshed from Google Patents.
US4097545A
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Heat-resistant thermosetting polyimide resin with bis-phenol-epichlorohydrin reaction product
Assignee: Toshiba Chemical Products Co Ltd
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Filing: 1976-08-30
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Granted: 1978-06-27
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Expires: 1996-08-30
Abstract
Abstract A heat-resistant thermosetting resin composition is obtained by reaction with each other of an N,N'-bis-imide of unsaturated dicarboxylic acid (A), a cyanuric or isocyanuric acid or derivatives thereof (B), and at least one compound (C) selected from the group consisting of tetracarboxylic acid diimide, hydantoin and derivatives thereof, and barbituric acid and derivatives thereof. This resin composition has excellent heat-resistance and workability, and is employed for the use of a molding, laminated sheet, adhesive, etc.
Inventors
- 👤 Keiichi Akiyama
- 👤 Junichi Kamiuchi
- 👤 Itsuo Matsuda
- 👤 Takara Fujii
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:12
CPC Classifications
H; H01; H01B; H01B3/00; H01B3/18; H01B3/30; H01B3/303; H01B3/306; C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/124; C08G73/125
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
196 words
A heat-resistant thermosetting resin composition consisting essentially of a reaction product of components (A), (B) and (C) wherein: (A) is a mixture of (a) at least one N,N'-bisimide of unsaturated dicarboxlic acid expressed by the general formula: ##STR7## wherein R is a divalent radical having at least two carbon atoms and R' is a divalent radical having a carbon-carbon double bond, and (b) about 30% by weight based on the total weight of (a) plus (b) of a reaction product of bis-phenol with epichlorohydrin, (B) is at least one selected from the group consisting of cyanuric acid, isocyanuric acid and tris (epoxy propyl) isocyanurate, and (C) is at least one compound selected from the group consisting of pyromellitic diimide; benzophenone tetracarboxylic acid diimide; 2, 3, 5, 7-naphthalene-tetracarboxylic acid diimide; 3,3', 4, 4'-diphenyltetra-carboxylic acid diimide; hydantoin or derivative of the formula: ##STR8## wherein R 1 and R 2 may be the same or different and represent hydrogen or one to three carbon atom alkyl radicals, and barbituric acid or derivative of the formula: ##STR9## wherein R 3 and R 4 may be the same or different and represent hydrogen or one to five carbon atom alkyl radicals.
Claim 2
Dependent Claim
196 words
A heat-resistant thermosetting resin composition consisting essentially of a reaction product of components (A), (B) and (C) wherein: (A) is a mixture of (a) at least one N,N'-bisimide of unsaturated dicarboxlic acid expressed by the general formula: ##STR7## wherein R is a divalent radical having at least two carbon atoms and R' is a divalent radical having a carbon-carbon double bond, and (b) about 30% by weight based on the total weight of (a) plus (b) of a reaction product of bis-phenol with epichlorohydrin, (B) is at least one selected from the group consisting of cyanuric acid, isocyanuric acid and tris (epoxy propyl) isocyanurate, and (C) is at least one compound selected from the group consisting of pyromellitic diimide; benzophenone tetracarboxylic acid diimide; 2, 3, 5, 7-naphthalene-tetracarboxylic acid diimide; 3,3', 4, 4'-diphenyltetra-carboxylic acid diimide; hydantoin or derivative of the formula: ##STR8## wherein R 1 and R 2 may be the same or different and represent hydrogen or one to three carbon atom alkyl radicals, and barbituric acid or derivative of the formula: ##STR9## wherein R 3 and R 4 may be the same or different and represent hydrogen or one to five carbon atom alkyl radicals.
Claim 3
Dependent Claim
21 words
The heat-resistant thermosetting resin composition of claim 1 wherein component (B) is a tautomeric mixture of cyanuric acid and isocyanuric acid.
Claim 4
Dependent Claim
25 words
A heat-resistant thermosetting resin composition of claim 1 wherein said reaction product is prepared by reacting components (A), (B) and (C) in an inactive solvent.
Claim 5
Dependent Claim
34 words
The heat-resistant thermosetting resin composition of claim 3 wherein the component proportion ranges expressed in terms of mols are 0 < B/(B + C) ≦ 0.5, and 1 ≦ A/(B + C) < 2.
Claim 6
Dependent Claim
39 words
The heat resistant thermosetting resin composition of claim 4 wherein said component (a) is selected from the group consisting of N,N'-4,4"-diphenylmethane-bis-maleimide; N,N'-4,4"-diphenylether-bis maleimide; N,N'-p-phenylene-bis-maleimide; N,N'-benzidine-bis-maleimide; N,N'-metaxylene-bis-maleimide; N,N'-1,5-naphthalene-bis-maleimide; N,N'-1,5-naphthalene-bis-maleimide; N,N'-4,4'-diphenylsulphone-bis-maleimide; N,N'-2,2'-4,4'-dimethylene-cyclohexane-bis-maleimide; N,N'-4,4'-dicyclohexyl-methane-bis-maleimide; N,N'-4,4-diphenylcyclohexane-bis-maleimide; N,N'-4,4'-diphenylphenylamine-bis-maleimide; N,N'-4,4'-diphenyldiphenylsilane-bis-maleimide; N,N'-4,4'-diphenylsulfide-bis-maleimide; N,N'2,2'-(4,4'-diphenyl)-propane-bis-maleimide; N,N'-metaphenylene-bis-maleimide and N,N'-3,3'-(N,N'-metaphenylene-bis-benzamido)-bis-maleimide,
Claim 7
Dependent Claim
40 words
The heat-resistant thermosetting resin composition of claim 1 wherein said reaction product is prepared by reacting components (A), (B) and (C) in an inactive solvent selected from the group consisting of dimethyl formamide, dimethyl acetamide, dimethyl sulfoxide, N-methylpyrrolidone and hexamethylphosphoramide.
Claim 8
Dependent Claim
29 words
The heat-resistant thermosetting resin composition of claim 1 wherein said component (C) is selected from the group consisting of hydantoin; 5,5'-dimethylhydantoin; 5-n-propyl hydantoin and 5-isopropyl hydantoin, and mixtures thereof.
Claim 9
Dependent Claim
33 words
The heat-resistant thermosetting resin composition of claim 1 wherein said component (C) is selected from the group consisting of barbituric acid, barbital, phenolbarbital, amobarbital, pentobarbital, secobarbital, butabital, ethyl hexabital, butethal and mixtures thereof.
References Cited (Backward Citations)
US3770705A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |