Patent US4946908A successfully refreshed from Google Patents.
US4946908A
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Bismaleimide compositions containing high glass transition temperature and soluble reactive oligomers and composites prepared therefrom
Assignee: Hexcel Corp
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Filing: 1987-07-15
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Granted: 1990-08-07
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Expires: 2007-07-15
Abstract
Abstract Described are novel thermosetting maleimide compositions suitable for making cured resins, prepregs and tough thermoset composites. The thermosetting compositions comprise a multifunctional maleimide and terminally unsaturated polyamide, polyimide, or polyamideimide oligomer which is soluble in the composition. The cured resins have a fracture toughness, K ic , of at least 1.0 MPam 1/2 and a glass transition temperature of at least 200° C.
Inventors
- 👤 Sung G. Chu
- 👤 Harold Jabloner
- 👤 Tuyen T. Nguyen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 04:35
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/121; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/243; C08J5/249; C08L; C08L77/00; C08L77/06; C08L79/00; C08L79/04; C08L79/08; C08L79/085; C08J2379/00; C08J2379/04; C08J2379/08; Y; Y10; Y10S; Y10S525/00; Y10S525/907; Y10S525/928; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31721; Y10T428/31725
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
462 words
A thermosetting resin composition comprising a mono- or multifunctional maleimide, a terminally unsaturated polyimide, polyamide or polyimideamide oligomer and a reactive diluent, said mono- or multi-functional maleimide having the formula ##STR6## where R 1 is the residium of an aryl, alkylaryl, or alkylamine; R 2 is hydrogen, halogen, aryl, or lower alkyl group of from 1 to about 10 carbon atoms; R 3 is hydrogen, halogen, aryl or lower alkyl group of from 1 to about 10 carbon atoms; and n is an integer of from 1 to about 10; said terminally unsaturated polyimide, polyamide or polyimideamide oligomer prepared by reaction of (a) a diamine or mixture thereof selected from the group consisting of the formulae ##STR7## where R 4 is an alkyl, aryl, alkylaryl, halogen or hydrogen; R 5 is methyl or lower alkyl; n is 0 to 4; x is methylene and m is 3 to 6; Ar is aryl or alkylaryl; and R 6 is alkyl, aryl, arylalkyl, or halogen and the four R 6 groups are on adjacent carbon atoms to the two amine groups and such R 6 groups may be the same or different; (b) a dicarboxylic acid or reactive derivative thereof or mixture thereof and (c) an unsaturated organic compound having a group reactive with whichever of (a) or (b) is used in excess wherein if (a) is used in excess then said unsaturated organic compound is selected from maleic anhydride, its halide, alkyl, alkylaryl or aryl derivative; unsaturated alkyl halide; unsaturated acid chloride; unsaturated phosphonic halide; unsaturated isocyanate and unsaturated sulfonyl chloride; and if (b) is used in excess then said unsaturated organic compound is selected from unsaturated primary or secondary amine, unsaturated alcohol and unsaturated sulfide; and said reactive diluent being soluble in the mixture of said oligomer and said maleimide and selected from materials having formula VI or VII, below: ##STR8## wherein in formula VI R 7 represents one of the radical ##STR9## --SO 2 --, --SO--, --S-- and --O--; a is 0 to 1; and each Q is independently --OH, --NH 2 , --SH, or hydrogen, and are the same or different and R 8 and R 9 are unsaturated alkyl groups having one to eight carbon atoms and may be the same or different, and wherein the Formula VII, R 9 and R 11 are unsaturated alkyl or aryl groups and may be the same or different, R 10 and R 12 are hydrogen, or alkyl or aryl ether groups; each Q is independently --OH, --NH 2 , --SH or hydrogen and G is --O-- or --S--or --NH--, and A is the residium of a dihalide, said composition being a liquid at 60° to 100° C. with a viscosity of between about 10,000 and 100,000 centipoises (cps) at 100° C.
Claim 2
Dependent Claim
462 words
A thermosetting resin composition comprising a mono- or multifunctional maleimide, a terminally unsaturated polyimide, polyamide or polyimideamide oligomer and a reactive diluent, said mono- or multi-functional maleimide having the formula ##STR6## where R 1 is the residium of an aryl, alkylaryl, or alkylamine; R 2 is hydrogen, halogen, aryl, or lower alkyl group of from 1 to about 10 carbon atoms; R 3 is hydrogen, halogen, aryl or lower alkyl group of from 1 to about 10 carbon atoms; and n is an integer of from 1 to about 10; said terminally unsaturated polyimide, polyamide or polyimideamide oligomer prepared by reaction of (a) a diamine or mixture thereof selected from the group consisting of the formulae ##STR7## where R 4 is an alkyl, aryl, alkylaryl, halogen or hydrogen; R 5 is methyl or lower alkyl; n is 0 to 4; x is methylene and m is 3 to 6; Ar is aryl or alkylaryl; and R 6 is alkyl, aryl, arylalkyl, or halogen and the four R 6 groups are on adjacent carbon atoms to the two amine groups and such R 6 groups may be the same or different; (b) a dicarboxylic acid or reactive derivative thereof or mixture thereof and (c) an unsaturated organic compound having a group reactive with whichever of (a) or (b) is used in excess wherein if (a) is used in excess then said unsaturated organic compound is selected from maleic anhydride, its halide, alkyl, alkylaryl or aryl derivative; unsaturated alkyl halide; unsaturated acid chloride; unsaturated phosphonic halide; unsaturated isocyanate and unsaturated sulfonyl chloride; and if (b) is used in excess then said unsaturated organic compound is selected from unsaturated primary or secondary amine, unsaturated alcohol and unsaturated sulfide; and said reactive diluent being soluble in the mixture of said oligomer and said maleimide and selected from materials having formula VI or VII, below: ##STR8## wherein in formula VI R 7 represents one of the radical ##STR9## --SO 2 --, --SO--, --S-- and --O--; a is 0 to 1; and each Q is independently --OH, --NH 2 , --SH, or hydrogen, and are the same or different and R 8 and R 9 are unsaturated alkyl groups having one to eight carbon atoms and may be the same or different, and wherein the Formula VII, R 9 and R 11 are unsaturated alkyl or aryl groups and may be the same or different, R 10 and R 12 are hydrogen, or alkyl or aryl ether groups; each Q is independently --OH, --NH 2 , --SH or hydrogen and G is --O-- or --S--or --NH--, and A is the residium of a dihalide, said composition being a liquid at 60° to 100° C. with a viscosity of between about 10,000 and 100,000 centipoises (cps) at 100° C.
Claim 3
Dependent Claim
31 words
A thermosetting polyimide composition of claim 1, wherein said terminally unsaturated oligomer comprises a polyimide oligomer which is the reaction,, product of p-bis-(4-isopropylidene 2,6-dimethylaniline)benzene and 3,3'4,4'-benzophenonetetracarboxylic dianhydride reacted with sorboyl chloride.
Claim 4
Dependent Claim
33 words
A thermosetting polyimide composition of claim 1, wherein said terminally unsaturated oligomer comprises a polyimide oligomer which is the reaction product of p-bis-(4-iso-propylidene 2,6-dimethylaniline-benzene and 3,3',4,4'-benzophenonetetracarboxylic dianhydride reacted in the presence of 2-isopropenylanilane.
Claim 5
Dependent Claim
12 words
A thermosetting composition of claim 3, wherein said multi-functional-maleimide comprises benzene bismaleimide.
Claim 6
Dependent Claim
11 words
A thermosetting composition of claim 1, wherein said multi-functional-maleimide comprises diphenylmethanebismaleimide.
Claim 7
Dependent Claim
13 words
A thermosetting composition of claim 1, wherein said reactive diluent comprises 2,2-(3-alkenyl-4-hydroxyphenyl) propane.
Claim 8
Dependent Claim
18 words
A thermosetting composition of claim 1, wherein said reactive diluent comprises 3,3'-diallyl-2,2'-dihydroxybiphenyl and its positional and unsaturated isomers.
Claim 9
Dependent Claim
13 words
A thermosetting composition, of claim 1, wherein said reactive diluent comprises 4,4'-bis-(o-propenylphenoxy)-diphenyl sulfone.
Claim 10
Dependent Claim
44 words
A thermosetting composition in accordance with claim 1, wherein said diamine or mixture thereof is reacted in excess over the amount of said dicarboxylic acid or derivative so as to form said terminally unsaturated polyimide oligomer when said unsaturated organic compound is reacted therewith.
References Cited (Backward Citations)
US3179634A
Cited
US3416994A
Cited
US3528950A
Cited
US3575924A
Cited
US4035345A
Cited
US3970714A
Cited
US3897395A
Cited
US4110294A
Cited
US4100140A
Cited
US4160859A
Cited
US4518754A
Cited
US4362832A
Cited
US4298720A
Cited
US4351932A
Cited
US4539392A
Cited
US4579773A
Cited
US4654407A
Cited
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