US4487894A
Expired / Lapsed
US
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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: 1984-12-11
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Expires: 2002-09-20
Abstract
Abstract The resins described herein are polyimide-epoxy thermoset resins prepared by reacting a polyepoxide in two steps, first with a solution of a polyimide dianhydride and subsequently with a polyimide diamine, there being enough polyepoxide added initially to react completely with all the anhydride groups and preferably enough polyepoxide added initially to react with both the anhydride and amide groups. "Polyimide dianhydride" is an anhydride-terminated polyimide and "polyimide diamine" is an amine-terminated polyimide as represented by the respective formulas: ##STR1## and ##STR2## 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
2026-11-05 20:50
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/42; C08G59/423; C08G59/4007; C08G59/4014; C08G59/4042; C08L; C08L63/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
201 words
In a process of reacting a polyepoxide composition with a polyimide composition having terminal anhydride or amine groups, the improvement comprising: (a) first reacting said polyepoxide compositions with a solution of a polyimide dianhydride of the formula: ##STR28## at a temperature in the range of room temperature to about 120° C.; and (b) subsequently reacting the reaction product of (a) with a solution of a polyamide diamine of the formula: ##STR29## at a temperature in the range of 60° C. to 120° C.; in which formulas: Ar' is a tetravalent aromatic 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 where the Ar' is a naphthalene radical, one or both pairs of the 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 where the Ar' is 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 having a value of at least one.
Claim 2
Dependent Claim
201 words
In a process of reacting a polyepoxide composition with a polyimide composition having terminal anhydride or amine groups, the improvement comprising: (a) first reacting said polyepoxide compositions with a solution of a polyimide dianhydride of the formula: ##STR28## at a temperature in the range of room temperature to about 120° C.; and (b) subsequently reacting the reaction product of (a) with a solution of a polyamide diamine of the formula: ##STR29## at a temperature in the range of 60° C. to 120° C.; in which formulas: Ar' is a tetravalent aromatic 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 where the Ar' is a naphthalene radical, one or both pairs of the 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 where the Ar' is 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 having a value of at least one.
Claim 3
Dependent Claim
23 words
The process of claim 1 in which the temperature at which the reaction (a) is conducted is in the range of 50°-80° C.
Claim 4
Dependent Claim
23 words
The process of claim 2 in which the temperature at which the reaction (b) is conducted is in the range of 60°-90° C.
Claim 5
Dependent Claim
55 words
The process of claim 1 in which Ar' in both said polyimide dianhydride and said polyimide diamine has a formula selected from the group consisting of: ##STR30## in which last formula the members of each pair of valence bonds are on carbon times either adjacent to each other or in peri positions to each other.
Claim 6
Dependent Claim
22 words
The process of claim 1 in which said Ar' in both said polyimide dianhydride and said polyimide diamine has the formula: ##STR31##
Claim 7
Dependent Claim
27 words
The process of claim 5 in which said Ar group in both said polyimide dianhydride and said polyimide diamine is selected from the class consisting of: ##STR32##
Claim 8
Dependent Claim
21 words
The process of claim 5 in which said Ar in both said polyimide dianhydride and said polyimide diamine group is: ##STR33##
Claim 9
Dependent Claim
11 words
The process of claim 6 in which said Ar is: ##STR34##
Claim 10
Dependent Claim
24 words
A laminate produced by molding glass cloth impregnated with a solution of a polyimide-polyepoxide rection product produced according to the process of claim 1.
Claim 11
Dependent Claim
28 words
The laminated product of claim 9 in which said laminated product has been molded at a temperature of about 160°-180° C. and a pressure of about 100-500 psi.
Claim 12
Dependent Claim
14 words
The laminated product of claim 10 in which said pressure is about 200-300 psi.
Claim 13
Dependent Claim
25 words
The laminated product of claim 9 in which the solvent in said solution is selected from the group consisting of N-methyl-alpha-pyrrolidone, N,N-dimethyl-acetaminde and N,N-dimethyl formamide.
Claim 14
Dependent Claim
15 words
The laminated product of claim 9 in which the solvent in said solution is N-methyl-alpha-pyrrolidone.
Claim 15
Dependent Claim
29 words
The laminated product of claim 12 in which the Ar' in both said polyimide dianhydride and said polyimide diamine has a formula selected from the group consisting of: ##STR35##
Claim 16
Dependent Claim
13 words
The laminated product of claim 14 in which the said formula is: ##STR36##
Claim 17
Dependent Claim
30 words
The laminated product of claim 14 in which the Ar group of both said polyimide dianhydride and said polyimide diamine has a formula selected from the group consisting of: ##STR37##
Claim 18
Dependent Claim
13 words
The laminated product of claim 16 in which said Ar formula is ##STR38##
Claim 19
Dependent Claim
24 words
The laminated product of claim 15 in which the Ar group of both said polyimide dianhydride and said polyimide diamine has the formula: ##STR39##
Claim 20
Dependent Claim
13 words
The laminated product of claim 15 in which the Ar formula is: ##STR40##
Claim 21
Dependent Claim
13 words
The laminated product of claim 17 in which said Ar formula is: ##STR41##
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) | 1987-12-11 | 1988-06-11 | 1988-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-11 | 1992-06-11 | 1992-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-11 | 1996-06-11 | 1996-12-11 | $7700.00 | Window Closed / Lapsed |