US5153274A
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Curable thermosetting prepolymerised imide resin compositions
Assignee: UK Secretary of State for Defence
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Filing: 1990-04-17
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Granted: 1992-10-06
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Expires: 2010-04-17
Abstract
Abstract Curable thermosetting prepolymerized imide resin compositions are prepared by chemically reacting, at a temperature below 150° C., a liquid mixture of carboxy-terminated polybutadiene/acrylonitrile (CTBN) and a co-reactant comprising at least one N,N'-bisimide of an unsaturated carboxylic acid of formula (I) where B represents a divalent radical containing a carbon-carbon double bond and A represents a divalent radical having at least two carbon atoms to yield a curable thermosetting prepolymerized imide resin composition containing copolymerized CTBN and co-reactant. A resin composition prepared by this method may be cured at a temperature between 100° C. and 350° C. to yield a fully cross-linked polyimide matrix containing a dispersion of phase-separated solid particles of copolymerized CTBN and co-reactant, the matrix having a lapshear strength at 20° C. at least 50% greater than that of a fully cross-linked polyimide cured from the co-reactant alone.
Inventors
- 👤 Anthony J. Kinloch
- 👤 Stephen J. Shaw
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 22:03
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/30; C08C19/34; C08C19/36
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
156 words
A method for preparing a curable thermosetting prepolymerized imide resin composition comprising chemically reacting, at a temperature below 150° C., a liquid mixture of carboxy-terminated polybutadiene/acrylonitrile (CTBN) and a co-reactant comprising the imide resin reaction product of at least one primary organic diamine or organic hydrazine and at least one N,N'-bisimide of an unsaturated carboxylic acid of the formula I: ##STR8## where B represents a divalent radical containing a carbon-carbon double bond and A represents a divalent radical having at least two carbon atoms, to yield a curable thermosetting prepolymerized imide resin composition containing copolymerized CTBN and co-reactant, the composition being curable at a temperature between 100° C. and 350° C. to a fully cross-linked polyimide matrix containing a dispersion of phase separated solid particles of copolymerized CTBN and co-reactant, the matrix having a lap shear strength at 20° C. at least 50% greater than that of a fully cross-linked polyimide cured from the co-reactant alone.
Claim 2
Independent Claim
156 words
A method for preparing a curable thermosetting prepolymerized imide resin composition comprising chemically reacting, at a temperature below 150° C., a liquid mixture of carboxy-terminated polybutadiene/acrylonitrile (CTBN) and a co-reactant comprising the imide resin reaction product of at least one primary organic diamine or organic hydrazine and at least one N,N'-bisimide of an unsaturated carboxylic acid of the formula I: ##STR8## where B represents a divalent radical containing a carbon-carbon double bond and A represents a divalent radical having at least two carbon atoms, to yield a curable thermosetting prepolymerized imide resin composition containing copolymerized CTBN and co-reactant, the composition being curable at a temperature between 100° C. and 350° C. to a fully cross-linked polyimide matrix containing a dispersion of phase separated solid particles of copolymerized CTBN and co-reactant, the matrix having a lap shear strength at 20° C. at least 50% greater than that of a fully cross-linked polyimide cured from the co-reactant alone.
Claim 3
Dependent Claim
30 words
A method according to claim 1, wherein the average particle size of the phase separated particles, as determined by Scanning Electron Microscopy, lies in the range 0.1 to 10 microns.
Claim 4
Dependent Claim
30 words
A method according to claim 2, wherein the average particle size of the phase separated particles, as determined by Scanning Electron Microscopy, lies in the range 0.5 to 8 microns.
Claim 5
Dependent Claim
95 words
A method according to claim 1, wherein the co-reactant comprises the reaction product of at least one N,N'-bisimide of formula I where A and B are as defined in claim 13, and at least one primary organic diamine of the formula II: H.sub.2 N--D--NH.sub.2 (II) where D represents a divalent radical having not more than 30 carbon atoms, and wherein the ratio of the total number of moles of bisimide of formula I to the total number of moles of diamine of formula II in the reaction mixture lies in the range 1.2:1 to 50:1.
Claim 6
Dependent Claim
86 words
A method according to claim 1, wherein the co-reactant comprises the reaction product of at least one N,N'-bisimide of formula I where A and B are as defined in claim 1, and at least one organic hydrazide of the formula III: ##STR9## where E represents a divalent organic group, and wherein the ratio of the total number of moles of bisimide of formula I to the total number of moles of hydrazide of formula III in the reaction mixture lies in the range 1.1:1 to 10:1.
Claim 7
Dependent Claim
79 words
A method according to claim 1, wherein the co-reactant comprises the reaction product of at least one N,N'-bisimide of formula I where A and B are as defined in claim 13 and at least one organic hydrazide of the formula IV: ##STR10## where G represents a divalent organic group, and where the total number of moles of bisimide of formula I to the total number of moles of hydrazide of formula IV lies in the range 1.1:1 to 10:1.
Claim 8
Dependent Claim
14 words
A method according to claim 1, wherein B represents a group selected from: ##STR11##
Claim 9
Dependent Claim
64 words
A method according to claim 1, wherein the bisimide of formula I is at least one of the following: 1,2-bismaleimido ethane, 1,4-bismaleimido butane, 1,6-bismaleimido hexane, 1,12-bismaleimido dodecane, 1,6, -bismaleimido-(2,2-4-trimethyl)hexane, 1,3-bismaleimido benzene, 1,4-bismaleimido benzene, 4,4'-bismaleimido diphenyl methane, 4,4'-bismaleimido diphenyl ether, 4,4'-bismaleimido diphenyl sulfide, 4,4'-bismaleimido diphenyl sulfone, 4,4'-bismaleimido dicyclohexyl methane, 2,4-bismaleimido toluene, 2,6-bismaleimido toluene, N,N'-m-xylylene bismaleimide, N,N'-p-xylylene bismaleimide, N,N-m-phenylene biscitraconic acid imide, N,N'-4,4'-diphenylmethane citraconimide, N,N'-4,4'-diphenylmethane bisitaconimide.
Claim 10
Dependent Claim
29 words
A method according to claim 1, wherein the CTBN is of the formula VI: ##STR12## where the ratio of x to y lies in the range 99:1 to 65:35.
Claim 11
Dependent Claim
14 words
A curable thermosetting prepolymerized imide resin composition produced by the process of claim 1.
Claim 12
Dependent Claim
70 words
A method according to claim 1, including the additional step of heating the prepolymerized resin composition to a temperature between 100° C. and 350° C. to yield a fully cross-linked polymer matrix containing a dispersion of phase-separated solid particles of copolymerized CTBN and co-reactant, said matrix having a lap shear strength at 20° C. at least 50% greater than that of a fully cross-linked polyimide cured from the co-reactant alone.
Claim 13
Dependent Claim
23 words
A fully cross-linked polyimide matrix containing a dispersion of phase-separated solid particles of CTBN and co-reactant produced by the process of claim 11.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-10-06 | 1996-04-06 | 1996-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-10-06 | 2000-04-06 | 2000-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-10-06 | 2004-04-06 | 2004-10-06 | $7700.00 | Window Closed / Lapsed |