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US4283521A
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Curable aromatic epoxy-polyimide and cycloaliphatic epoxy-polyimide compositions
Assignee: Northrop Grumman Space and Mission Systems Corp
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Filing: 1979-02-14
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Granted: 1981-08-11
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Expires: 1999-02-14
Abstract
Abstract A prepolymer is comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide in combination with an aromatic and/or a cycloaliphatic epoxy resin providing at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.
Inventors
- 👤 Robert J. Jones
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 08:22
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/126; C08G73/127; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4042; C08G59/50; C08G59/56; C08G73/121; C08G73/123; C08G73/125; C08L; C08L63/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
226 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR26## wherein Z is a polyaliphatic ether in which each aliphatic group individually contains from one to about six carbon atoms, and in which each R is independently selected from the group consisting of hydrogen, an aliphatic group containing one or two carbon atoms, a benzenoid radical and a halogen; (ii) at least one aromatic polyamine; and (iii) at least one aromatic bismaleimide of the formula: ##STR27## wherein each R is independently selected from the group consisting of hydrogen, an aliphatic group containing one or two carbon atoms, a benzenoid radical and a halogen and wherein R' is a bifunctional benzenoid radical selected from the group consisting of: ##STR28## wherein X is selected from the group consisting of: --O--, --S--, --SO 2 --, --CH 2 --, --C 2 H 4 --, --CO--, --C 3 H 6 --, and ##STR29## and; (b) at least one aromatic epoxy resin of the formula: ##STR30## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR31## and each R" is independently selected from the group consisting of --H, and ##STR32##
Claim 2
Dependent Claim
226 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR26## wherein Z is a polyaliphatic ether in which each aliphatic group individually contains from one to about six carbon atoms, and in which each R is independently selected from the group consisting of hydrogen, an aliphatic group containing one or two carbon atoms, a benzenoid radical and a halogen; (ii) at least one aromatic polyamine; and (iii) at least one aromatic bismaleimide of the formula: ##STR27## wherein each R is independently selected from the group consisting of hydrogen, an aliphatic group containing one or two carbon atoms, a benzenoid radical and a halogen and wherein R' is a bifunctional benzenoid radical selected from the group consisting of: ##STR28## wherein X is selected from the group consisting of: --O--, --S--, --SO 2 --, --CH 2 --, --C 2 H 4 --, --CO--, --C 3 H 6 --, and ##STR29## and; (b) at least one aromatic epoxy resin of the formula: ##STR30## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR31## and each R" is independently selected from the group consisting of --H, and ##STR32##
Claim 3
Dependent Claim
39 words
A composition as claimed in claim 1 in which the aliphatic bismaleimide is of the formula: ##STR33## where the sum of a and c is equal to about 3.5 and b is equal to about 13.5 to about 45.5.
Claim 4
Dependent Claim
36 words
A composition as claimed in claim 1 in which the aliphatic bismaleimide is of the formula: ##STR34## where the sum of a and c is equal to about 3.5 and b is equal to about 20.5.
Claim 5
Dependent Claim
87 words
A composition as claimed in claim 1 in which the aromatic polyamine is selected from the group consisting of amines of the formula: NH.sub.2 --R'--NH.sub.2 wherein R' is a bifunctional benzenoid radical selected from the group consisting of: ##STR35## wherein X is selected from the group consisting of: --0--, --S--, --SO 2 --, --CH 2 --, --C 2 H 4 --, --CO--, --C 3 H 6 --, and ##STR36## amines of the formula: ##STR37## wherein d has a value from 0 to about 5, and mixtures thereof.
Claim 6
Dependent Claim
29 words
A composition as claimed in claim 1 in which the aromatic polyamine is selected from the group consisting of methylenedianiline, an amine of the formula: ##STR38## and mixtures thereof.
Claim 7
Dependent Claim
16 words
A composition as claimed in claim 1 in which the aromatic bismaleimide has the formula: ##STR39##
Claim 8
Dependent Claim
28 words
A composition as claimed in claim 1 in which the epoxy resin has the formula: ##STR40## wherein m has an average value of from 1 to about 5.
Claim 9
Dependent Claim
26 words
A composition as claimed in claim 7 in which the epoxy resin has a viscosity of from about 11,000 to about 14,000 cps at 25° C.
Claim 10
Dependent Claim
17 words
A composition as claimed in claim 1 in which the epoxy resin is of the formula: ##STR41##
Claim 11
Dependent Claim
26 words
A composition as claimed in claim 1 in which the epoxy resin is of the formula: ##STR42## wherein n' has an average value of about 1.
Claim 12
Dependent Claim
150 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR43## where the sum of a and c is equal to about 3.5 and b is equal to about 13.5 to about 45.5; and (ii) an aromatic polyamine selected from the group consisting of methylene dianiline, an amine of the formula: ##STR44## wherein d has a value of from 0 to about 5 and mixtures thereof. (iii) an aromatic bismaleimide of the formula: ##STR45## (b) at least one aromatic epoxy resin of the formula: ##STR46## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR47## and each R" is independently selected from the group consisting of --H, and ##STR48##
Claim 13
Dependent Claim
150 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR43## where the sum of a and c is equal to about 3.5 and b is equal to about 13.5 to about 45.5; and (ii) an aromatic polyamine selected from the group consisting of methylene dianiline, an amine of the formula: ##STR44## wherein d has a value of from 0 to about 5 and mixtures thereof. (iii) an aromatic bismaleimide of the formula: ##STR45## (b) at least one aromatic epoxy resin of the formula: ##STR46## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR47## and each R" is independently selected from the group consisting of --H, and ##STR48##
Claim 14
Dependent Claim
35 words
A composition as claimed in claim 11 where the aliphatic bismaleimide has the general formula: ##STR49## and the sum of a and c is equal to about 3.5 and b is equal to about 20.5.
Claim 15
Dependent Claim
19 words
A composition as claimed in claim 11 in which the aromatic polyamine is an amine of the formula: ##STR50##
Claim 16
Dependent Claim
28 words
A composition as claimed in claim 11 in which the epoxy resin has the formula: ##STR51## wherein m has an average value of from 1 to about 5.
Claim 17
Dependent Claim
25 words
A composition as claimed in claim 14 in which the epoxy resin has a viscosity from about 11,000 to about 14,000 cps at 25° C.
Claim 18
Dependent Claim
17 words
A composition as claimed in claim 11 in which the epoxy resin is of the formula: ##STR52##
Claim 19
Dependent Claim
26 words
A composition as claimed in claim 11 in which the epoxy resin is of the formula: ##STR53## wherein n' has an average value of about 1.
Claim 20
Dependent Claim
28 words
A composition as claimed in claim 12 in which the epxoy resin has the formula: ##STR54## wherein m has an average value of from 1 to about 5.
Claim 21
Dependent Claim
26 words
A composition as claimed in claim 18 in which the epoxy resin has a viscosity of from about 11,000 to about 14,000 cps at 25° C.
Claim 22
Dependent Claim
17 words
A composition as claimed in claim 12 in which the epoxy resin is of the formula: ##STR55##
Claim 23
Dependent Claim
26 words
A composition as claimed in claim 12 in which the epoxy resin is of the formula: ##STR56## wherein n' has an average value of about 1.
Claim 24
Dependent Claim
28 words
A composition as claimed in claim 13 in which the epoxy resin has the formula: ##STR57## wherein m has an average value of from 1 to about 5.
Claim 25
Dependent Claim
26 words
A composition as claimed in claim 22 in which the epoxy resin has a viscosity of from about 11,000 to about 14,000 cps at 25° C.
Claim 26
Dependent Claim
17 words
A composition as claimed in claim 13 in which the epoxy resin is of the formula: ##STR58##
Claim 27
Dependent Claim
26 words
A composition as claimed in claim 13 in which the epoxy resin is of the formula: ##STR59## wherein n' has an average value of about 1.
Claim 28
Dependent Claim
117 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR60## where the sum of a and c is equal to about 3.5 and b is equal to about 20.5; (ii) methylene dianaline; (iii) an aromatic bismaleimide of the formula: ##STR61## (b) at least one aromatic epoxy resin of the formula: ##STR62## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR63## and each R" is independently selected from the group consisting of --H, and ##STR64##
Claim 29
Dependent Claim
117 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR60## where the sum of a and c is equal to about 3.5 and b is equal to about 20.5; (ii) methylene dianaline; (iii) an aromatic bismaleimide of the formula: ##STR61## (b) at least one aromatic epoxy resin of the formula: ##STR62## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR63## and each R" is independently selected from the group consisting of --H, and ##STR64##
Claim 30
Dependent Claim
28 words
A composition as claimed in claim 26 in which the epoxy resin has the formula: ##STR65## wherein m has an average value of from 1 to about 5.
Claim 31
Dependent Claim
26 words
A composition as claimed in claim 27 in which the epoxy resin has a viscosity of from about 11,000 to about 14,000 cps at 25° C.
Claim 32
Dependent Claim
17 words
A composition as claimed in claim 26 in which the epoxy resin is of the formula: ##STR66##
Claim 33
Dependent Claim
26 words
A composition as claimed in claim 26 in which the epoxy resin is of the formula: ##STR67## wherein n' has an average value of about 1.
Claim 34
Dependent Claim
123 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR68## where the sum of a and c is equal to about 3.5 and b is equal to about 20.5; and (ii) an aromatic polyamine of the formula: ##STR69## (iii) an aromatic bismaleimide of the formula: ##STR70## (b) at least one aromatic epoxy resin of the formula: ##STR71## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR72## and each R" is independently selected from the group consisting of --H, and ##STR73##
Claim 35
Dependent Claim
123 words
A low temperature curable composition comprising: (a) at least one curable polyimide prepolymer formed at a temperature sufficient to cause thermal reaction between heated components of a mixture of: (i) at least one aliphatic bismaleimide of the formula: ##STR68## where the sum of a and c is equal to about 3.5 and b is equal to about 20.5; and (ii) an aromatic polyamine of the formula: ##STR69## (iii) an aromatic bismaleimide of the formula: ##STR70## (b) at least one aromatic epoxy resin of the formula: ##STR71## wherein n has an average value of from 0 to about 6; each X' is independently selected from the group consisting of: ##STR72## and each R" is independently selected from the group consisting of --H, and ##STR73##
Claim 36
Dependent Claim
28 words
A composition as claimed in claim 31 in which the epoxy resin has the formula: ##STR74## wherein m has an average value of from 1 to about 5.
Claim 37
Dependent Claim
26 words
A composition as claimed in claim 32 in which the epoxy resin has a viscosity of from about 11,000 to about 14,000 cps at 25° C.
Claim 38
Dependent Claim
17 words
A composition as claimed in claim 31 in which the epoxy resin is of the formula: ##STR75##
Claim 39
Dependent Claim
26 words
A composition as claimed in claim 31 in which the epoxy resin is of the formula: ##STR76## wherein n' has an average value of about 1.
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) | 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 |