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US4410664A
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Polyimide-epoxy thermoset resins
Assignee: Plastics Engineering Co
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Filing: 1982-09-20
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Granted: 1983-10-18
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Expires: 2002-09-20
Abstract
Abstract The resins described herein are polyimide-epoxy thermoset resins prepared by reacting a polyepoxide with a solution of an admixture of a polyimide dianhydride with another polyimide component, either a polyimide dianhydride or a polyimide diamine, at least one of which polyimide components is insoluble in the particular solvent in the absence of the other polyimide component or components. "Polyimide dianhydride" is an anhydride-terminated polyimide and "polyimide diamine" is an amine-terminated polyimide as represented by the respective formulas: ##STR1## wherein Ar', Ar and n are as defined hereinafter. For use in the present compositions, the polyimide dianhydride has an anhydride activity of at least 0.17 as defined herein, and the ratio of epoxy equivalent to anhydride plus amine equivalents is at least 1/1. By employing a two step reaction scheme, the process offers a more tractable polyimide-epoxy intermediate resin that can be processed into void-free products with superior mechanical properties than polyimide-epoxy thermosets shown in the prior art.
Inventors
- 👤 Chung J. Lee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:16
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1067; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4042; C08G73/1003
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
282 words
The process of reacting a polyepoxide with a solution of a polyimide dianhydride together with another polyimide component selected from the class consisting of polyimide dianhydrides and polyimide diamines, at least one of which polyimide components is insoluble in the selected solvent in the absence of said other polyimide component or components, the proportion of the said insoluble component or components representing 15 to 65 percent by weight of the total combined weight of said polyimide components, the anhydride activity of each of said polyimide dianhydride components being at least 0.17 as determined by the infrared spectrum, and the ratio of epoxy equivalents to anhydride plus amine equivalents being at least 1:1, the concentration of said polyimide components in said solvent comprising at least 5 percent by weight, in which polyimide components the polyimide dianhydride is represented by the formula: ##STR28## and the polyimide diamine is represented by the formula: ##STR29## wherein Ar' is a tetravalent aromatic organic radical, the four carbonyl groups being attached directly to separate carbon atoms and each pair of carbonyl groups being attached to adjacent carbon atoms in the Ar' radical except that in the case of the Ar' being a naphthalene radical one or both pairs of the carbonyl groups may be attached to peri carbon atoms; Ar is a divalent aromatic radical; and n is an integer of at least one; in which polyimide components there may be as much as 50 percent of the cyclic polyimide structure in the intermediate amic acid structure, the solubility of said polyimide components being determined by heating one gram of said component in 4 ml. of the selected solvent at a temperature of 167° C. for 5 minutes.
Claim 2
Dependent Claim
282 words
The process of reacting a polyepoxide with a solution of a polyimide dianhydride together with another polyimide component selected from the class consisting of polyimide dianhydrides and polyimide diamines, at least one of which polyimide components is insoluble in the selected solvent in the absence of said other polyimide component or components, the proportion of the said insoluble component or components representing 15 to 65 percent by weight of the total combined weight of said polyimide components, the anhydride activity of each of said polyimide dianhydride components being at least 0.17 as determined by the infrared spectrum, and the ratio of epoxy equivalents to anhydride plus amine equivalents being at least 1:1, the concentration of said polyimide components in said solvent comprising at least 5 percent by weight, in which polyimide components the polyimide dianhydride is represented by the formula: ##STR28## and the polyimide diamine is represented by the formula: ##STR29## wherein Ar' is a tetravalent aromatic organic radical, the four carbonyl groups being attached directly to separate carbon atoms and each pair of carbonyl groups being attached to adjacent carbon atoms in the Ar' radical except that in the case of the Ar' being a naphthalene radical one or both pairs of the carbonyl groups may be attached to peri carbon atoms; Ar is a divalent aromatic radical; and n is an integer of at least one; in which polyimide components there may be as much as 50 percent of the cyclic polyimide structure in the intermediate amic acid structure, the solubility of said polyimide components being determined by heating one gram of said component in 4 ml. of the selected solvent at a temperature of 167° C. for 5 minutes.
Claim 3
Dependent Claim
26 words
The process of claim 1, in which the portion of insoluble polyimide component represents 15-50 percent by weight of the combined weight of said polyimide components.
Claim 4
Dependent Claim
23 words
The process of claim 2, in which the concentration of said polyimide components in said solvent comprises at least 20 percent by weight.
Claim 5
Dependent Claim
20 words
The process of claim 1, in which the reaction with the polyepoxide is conducted at a temperature of 25°-130° C.
Claim 6
Dependent Claim
20 words
The process of claim 1, in which the solvent is selected from the class consisting of N,N-dimethylformamide, N,N-dimethylacetamide and N,N-methyl-pyrrolidone.
Claim 7
Dependent Claim
30 words
The process of claim 5, in which the soluble polyimide component is selected from the class consisting of polyimides prepared by the reaction of 3,4,3',4'-benzophenonetetracarboxylic dianhydride with 2,4-toluenediamine or m-aminophenylenesulfone.
Claim 8
Dependent Claim
40 words
The process of claim 6, in which the insoluble polyimide component is prepared by the reaction of 3,4,3',4'-benzophenonetetracarboxylic dianhydride with a diamine selected from the class consisting of: (a) oxydianiline (b) 3,3'-dimethoxybenzidine (c) 2,6-diaminoanthraquinone (d) m-phenylenediamine (e) p-phenylenediamine (f) naphthalenediamine
Claim 9
Dependent Claim
37 words
The process of claim 1, in which the polyepoxide has the structural formula ##STR30## wherein Z is an organic radical having a valency of m, and m is an integer having a value of at least 2.
Claim 10
Dependent Claim
13 words
The process of claim 8, in which m has a value of 2-20.
Claim 11
Dependent Claim
33 words
The process of claim 8, in which the polyepoxide resin is a Novolak resin having at least two glycidyl groups attached to aromatic nuclei therein through the oxygen of the original hydroxy groups.
Claim 12
Dependent Claim
20 words
The process of claim 8, in which the polyepoxide is a polyglycidyl acrylate, a polyglycidyl methacrylate or a polyglycidyl chloracrylate.
Claim 13
Dependent Claim
20 words
The process of claim 1, in which the ratio of equivalents of epoxide to anhydride is no less than 2/1.
Claim 14
Dependent Claim
35 words
The process of claim 1, in which the molar ratio of polyimide dianhydride is in the range of 0.50-2 per mole of polyimide diamine and outside the range of 0.9 to 1.10 of polyimide diamine.
Claim 15
Dependent Claim
9 words
The product made by the process of claim 1.
Claim 16
Dependent Claim
27 words
The cured product made by removal of solvent from the product of claim 14 and thereafter curing the product at a temperature of at least 120° C.
Claim 17
Dependent Claim
15 words
The cured product of claim 15, in which said temperature is at least 150° C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-17 | 1987-04-18 | 1987-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-17 | 1991-04-18 | 1991-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-17 | 1995-04-18 | 1995-10-18 | $7700.00 | Window Closed / Lapsed |