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US4889912A
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Acetylene terminated aspartimides and resins therefrom
Assignee: National Aeronautics and Space Administration
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Filing: 1989-03-24
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Granted: 1989-12-26
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Expires: 2009-03-24
Abstract
Abstract Acetylene terminated aspartimides are prepared using two methods. In the first, an amino-substituted aromatic acetylene is reacted with an aromatic bismaleimide in a solvent of glacial acetic acid and/or m-c=resol. In the second method, an aromatic diamine is reacted with an ethynyl containing maleimide, such as N-(3-ethynylphenyl) maleimide, in a solvent of glacial acetic acid and/or m-cresol. In addition, acetylene terminated aspartimides are blended with various acetylene terminated oligomers and polymers to yield composite materials exhibiting improved mechanical properties.
Inventors
- 👤 Paul M. Hergenrother
- 👤 John W. Connell
- 👤 Stephen J. Havens
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:54
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1092; C08F; C08F299/00; C08F299/02; C08F299/022; C08G73/12; C08G73/121; C08G73/122; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/243; C08J2379/00; C08J2379/04; C08J2379/08
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
46 words
The class of acetylene terminated aspartimides having the general formula: ##STR12## where X is a bond or a divalent radical selected from the group consisting of CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR13##
Claim 2
Dependent Claim
46 words
The class of acetylene terminated aspartimides having the general formula: ##STR12## where X is a bond or a divalent radical selected from the group consisting of CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR13##
Claim 3
Dependent Claim
46 words
The class of acetylene terminated aspartimide oligomers having the general formula ##STR14## where n is an integer from one to sixty; X is a divalent radical selected from the group consisting of: ##STR15## and Ar is a divalent radical selected from the group consisting of: ##STR16##
Claim 4
Dependent Claim
46 words
The class of acetylene terminated aspartimide oligomers having the general formula ##STR14## where n is an integer from one to sixty; X is a divalent radical selected from the group consisting of: ##STR15## and Ar is a divalent radical selected from the group consisting of: ##STR16##
Claim 5
Dependent Claim
46 words
The class of acetylene terminated aspartimides having the general formula: ##STR17## where X is a bond or a divalent radical selected from the group consisting of CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR18##
Claim 6
Dependent Claim
46 words
The class of acetylene terminated aspartimides having the general formula: ##STR17## where X is a bond or a divalent radical selected from the group consisting of CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR18##
Claim 7
Dependent Claim
46 words
The class of acetylene terminated aspartimide oligomers having the general formula: ##STR19## where n is an integer from one to sixty; X is a divalent radical selected from the group consisting of ##STR20## and Ar is a divalent radical selected from the group consisting of: ##STR21##
Claim 8
Dependent Claim
46 words
The class of acetylene terminated aspartimide oligomers having the general formula: ##STR19## where n is an integer from one to sixty; X is a divalent radical selected from the group consisting of ##STR20## and Ar is a divalent radical selected from the group consisting of: ##STR21##
Claim 9
Dependent Claim
18 words
An acetylene terminated aspartimide according to claim 1 and any other acetylene terminated oligomer in intimate contact therewith.
Claim 10
Dependent Claim
19 words
An acetylene terminated aspartimide oligomer according to claim 2 and any other acetylene terminated oligomer in intimate contact therewith.
Claim 11
Dependent Claim
29 words
A composition according to claim 5 wherein said acetylene terminated oligomer is an acetylene terminated polysulfone having the formula: ##STR22## where i is an integer from three to fifty-nine.
Claim 12
Dependent Claim
154 words
A composition according to claim 5 wherein said acetylene terminated oligomer is an acetylene terminated polyarylene ether having the following formula: ##STR23## wherein n is an integer representing 3 to 60 repeat units, linkage of the phenylether groups being either meta or para; Ar is a divalent aromatic radical selected from the group consisting of: ##STR24## where X is selected from the group consisting of O═C and SO 2 , and Y is a bond, or is a member selected from the group consisting of O, S, CH 2 , C═O, SO 2 , C(CH 3 ) 2 , and C(CF 3 ) 2 ; and Ar' is a divalent aromatic radical selected from the group consisting of: ##STR25## wherein X is a bond or is a member selected from the group consisting of: CH 2 , O, S, O═C, SO 2 , C(CH 3 ) 2 , and C(CF 3 ) 2 .
Claim 13
Dependent Claim
17 words
A composition according to claim 5 wherein said acetylene terminated oligomer is an acetylene terminated phenylquinoxaline oligomer.
Claim 14
Dependent Claim
17 words
A composition according to claim 5 wherein said acetylene terminated oligomer is an acetylene terminated imide oligomer.
Claim 15
Dependent Claim
17 words
A composition according to claim 5 wherein said acetylene terminated oligomer is an acetylene terminated ester oligomer.
Claim 16
Dependent Claim
18 words
An acetylene terminated aspartimide according to claim 3 and any other acetylene terminated oligomer in intimate composition therewith.
Claim 17
Dependent Claim
19 words
An acetylene terminated aspartimide oligomer according to claim 4 and any other acetylene terminated oligomer in intimate composition therewith.
Claim 18
Dependent Claim
29 words
A composition according to claim 12 wherein said acetylene terminated oligomer is an acetylene terminated polysulfone having the formula: ##STR26## where i is an integer from three to fifty-nine.
Claim 19
Dependent Claim
150 words
A composition according to claim 12 wherein said acetylene terminated oligomer is an acetylene terminated polyarylene ether having the following formula: ##STR27## wherein n is an integer representing 3 to 60 repeat units, linkage of the phenylether groups being either meta or para; Ar is a divalent aromatic radical selected from the group consisting of: ##STR28## wherein X is selected from the group consisting of O═C and SO 2 , and Y is a bond, or is a member selected from the group consisting of O, S, CH 2 , C═O, SO 2 , C(CH 3 ) 2 , and C(CF 3 ) 2 ; and Ar' is a divalent aromatic radical selected from the group consisting of: ##STR29## wherein X is a bond or is selected from the group: CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , and C(CF 3 ) 2 .
Claim 20
Dependent Claim
17 words
A composition according to claim 12 wherein said acetylene terminated oligomer is an acetylene terminated phenylquinoxaline oligomer.
Claim 21
Dependent Claim
17 words
A composition according to claim 12 wherein said acetylene terminated oligomer is an acetylene terminated imide oligomer.
Claim 22
Dependent Claim
17 words
A composition according to claim 12 wherein said acetylene terminated oligomer is an acetylene terminated ester oligomer.
Claim 23
Dependent Claim
84 words
A process for preparing an acetylene-terminated aspartimide having the formula: ##STR30## where X is a bond or a divalent radical selected from the group consisting of CH 2 , O, S, O═C, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR31## comprising the steps of: reacting an amino-substituted aromatic acetylene with an aromatic bismaleimide having the formula: ##STR32## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene-terminated aspartimide.
Claim 24
Dependent Claim
84 words
A process for preparing an acetylene-terminated aspartimide having the formula: ##STR30## where X is a bond or a divalent radical selected from the group consisting of CH 2 , O, S, O═C, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR31## comprising the steps of: reacting an amino-substituted aromatic acetylene with an aromatic bismaleimide having the formula: ##STR32## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene-terminated aspartimide.
Claim 25
Dependent Claim
84 words
A process for preparing acetylene terminated aspartimide oligomers having the formula ##STR33## wherein n is a integer from one to sixty; X is a divalent radical selected from the group consisting of: ##STR34## and Ar is a divalent radical selected from the group consisting of: ##STR35## comprising the steps of: reacting an amino-substituted aromatic acetylene with aromatic bismaleimide oligomers having the formula: ##STR36## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene-terminated aspartimide.
Claim 26
Dependent Claim
84 words
A process for preparing acetylene terminated aspartimide oligomers having the formula ##STR33## wherein n is a integer from one to sixty; X is a divalent radical selected from the group consisting of: ##STR34## and Ar is a divalent radical selected from the group consisting of: ##STR35## comprising the steps of: reacting an amino-substituted aromatic acetylene with aromatic bismaleimide oligomers having the formula: ##STR36## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene-terminated aspartimide.
Claim 27
Dependent Claim
90 words
A process for preparing an acetylene terminated aspartimide having the formula: ##STR37## wherein X is a bond or a divalent radical selected from the group consisting of: CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR38## comprising the steps of: reacting an aromatic diamine having the formula: ##STR39## with an ethynyl containing maleimide having the formula: ##STR40## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene terminated aspartimide.
Claim 28
Dependent Claim
90 words
A process for preparing an acetylene terminated aspartimide having the formula: ##STR37## wherein X is a bond or a divalent radical selected from the group consisting of: CH 2 , O, S, C═O, SO 2 , C(CH 3 ) 2 , C(CF 3 ) 2 , ##STR38## comprising the steps of: reacting an aromatic diamine having the formula: ##STR39## with an ethynyl containing maleimide having the formula: ##STR40## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene terminated aspartimide.
Claim 29
Dependent Claim
90 words
A process for preparing acetylene terminated aspartimide oligomers having the general formula: ##STR41## where n is an integer from one to sixty; X is a divalent radical selected from the group consisting of: ##STR42## and Ar is a divalent radical selected from the group consisting of: ##STR43## comprising the steps of: reacting aromatic diamine oligomers having the formula: ##STR44## with an ethynyl containing maleimide having the formula: ##STR45## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene terminated aspartimide.
Claim 30
Dependent Claim
90 words
A process for preparing acetylene terminated aspartimide oligomers having the general formula: ##STR41## where n is an integer from one to sixty; X is a divalent radical selected from the group consisting of: ##STR42## and Ar is a divalent radical selected from the group consisting of: ##STR43## comprising the steps of: reacting aromatic diamine oligomers having the formula: ##STR44## with an ethynyl containing maleimide having the formula: ##STR45## in a polar solvent; evaporating said polar solvent; and removing all traces of the polar solvent to produce said acetylene terminated aspartimide.
References Cited (Backward Citations)
US3533996A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-12-25 | 1993-06-26 | 1993-12-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-12-25 | 1997-06-26 | 1997-12-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-12-25 | 2001-06-26 | 2001-12-26 | $7700.00 | Window Closed / Lapsed |