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US4946908A Expired / Lapsed US ⏱️ 0.0 years remaining

Bismaleimide compositions containing high glass transition temperature and soluble reactive oligomers and composites prepared therefrom

Assignee: Hexcel Corp
•
Filing: 1987-07-15
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Granted: 1990-08-07
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Expires: 2007-07-15
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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 03:19
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.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-08-06 1994-02-05 1994-08-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-08-06 1998-02-05 1998-08-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-08-06 2002-02-05 2002-08-07 $7700.00 Window Closed / Lapsed

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