Patent US4789704A successfully refreshed from Google Patents.
US4789704A
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US
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Curable resin from bis maleimide and alkenyl phenyl hydroxy ether
Assignee: Evonik Operations GmbH
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Filing: 1986-12-17
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Granted: 1988-12-06
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Expires: 2006-12-17
Abstract
Abstract Cured resins of high fracture toughness are prepared from N,N'-bisimides of formula I <IMAGE> (I) and alkenyl compounds of formula II D(G)m II in which D is an m-valent group and G represents a phenyl ring having at least one alkenyl (e.g. allyl or 1-propenyl) substituent.
Inventors
- 👤 Horst Stenzenberger
- 👤 Peter Koenig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:11
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08F; C08F222/00; C08F222/36; C08F222/40; C08F222/404; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/3154; Y10T428/31721; Y10T428/31855
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
89 words
Curable resin comprising a mixture of (a) at least one bisimide of the general formula I ##STR17## in which B represents a divalent radical containing a carbon-carbon double bond and A is a divalent radical containing at least two carbon atoms and (b) at least one alkenyl compound of formula IIg G[OCH.sub.2 CH(OH)CH.sub.2 O]E[OCH.sub.2 CH(OH)CH.sub.2 O]G (IIg) in which E is a m-phenylene group or a group of formula IIh ##STR18## and G represents a group of formula IIj or IIk ##STR19## or of formula IIm or IIn ##STR20##
Claim 2
Dependent Claim
89 words
Curable resin comprising a mixture of (a) at least one bisimide of the general formula I ##STR17## in which B represents a divalent radical containing a carbon-carbon double bond and A is a divalent radical containing at least two carbon atoms and (b) at least one alkenyl compound of formula IIg G[OCH.sub.2 CH(OH)CH.sub.2 O]E[OCH.sub.2 CH(OH)CH.sub.2 O]G (IIg) in which E is a m-phenylene group or a group of formula IIh ##STR18## and G represents a group of formula IIj or IIk ##STR19## or of formula IIm or IIn ##STR20##
Claim 3
Dependent Claim
181 words
Curable bisimide resin according to claim 1 in which the bisimide of the general formula I is characterised in that A is a member selected from the groups consisting of (a) an alkylene group with up to 12 carbon atoms, (b) a cycloalkylene group with 5 or 6 carbon atoms, (c) a heterocyclic group with 4 to 5 carbn atoms and at least one nitrogen, oxygen or sulphur atom in the ring, (d) a mono or dicarbocyclic group, (e) at least two mono or dicarbocyclic aromatic or cycloalkylene groups which are connected to one another by a direct carbon-carbon bond or by a bivalent group chosen from oxygen, sulphur, alkylene with one to three carbon atoms, or a group of formulae IIIa to IIIj ##STR21## the radicals R 1 , R 2 , R 3 , R 4 , being alkyl groups with one to five carbon atoms, R 5 being an alkylene group or an arylene group and B is a group which is capable of addition polymerization selected from a group of formula IV, V, VI or VII ##STR22##
Claim 4
Dependent Claim
42 words
Curable bisimide resin as claimed in claim 2 in which the bisimide of formula I is selected from the group consisting of 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 1,12-bismaleimidododecane, 1,6-bismaleimido(2,2,4-trimethyl)hexane, 1,3-bismaleimidobenzene, 1,4-bismaleimidobenzene, 4,4'-bismaleimidodiphenylmethane, 4,4'-bismaleimidodiphenylether, 4,4'-bismaleimidodiphenylsulphide, 3,3'-bismaleimidodiphenylsulphone, 4,4'-bismaleimidodiphenylsulphone, 4,4'-bismaleimidodicyclohexylmethane, 2,4-bismaleimidotoluene, 2,6-bismaleimidotoluene, 2,4-bismaleimidoanisole, N,N'-m-xylylenebismaleimide, N,N'-p-xylylenebismaleimide and mixtures thereof.
Claim 5
Dependent Claim
39 words
Curable bisimide resin as claimed in claim 3 in which the bisimide of formula I comprises (i) eutectic mixtures containing 4,4'-bismaleimidodiphenylmethane and 2,4-bismaleimidotoluene, (ii) eutectic mixtures containing 4,4'-bismaleimidodiphenylmethane, 2,4-bismaleimidotoluene and 1,6-bismaleimido(2,2,4-trimethyl)hexane and (iii) eutectic mixtures of 4,4'-bismaleimidodiphenylmethane and 2,4-bismaleimidoanisole.
Claim 6
Dependent Claim
35 words
Curable bisimide resin as claimed in claim 1 wherein the ratio of the number of moles of bisimide present to the number of moles of alkenyl compound present lies in the range 1:1 to 50:1.
Claim 7
Dependent Claim
32 words
Curable resin as claimed in claim 1 in which a catalyst is present in an amount of 0.01 to 10% by weight based on the total weight of the curable bisimide resin.
Claim 8
Dependent Claim
30 words
Prepolymer obtained by heating the curable resin as claimed in claim 1 to temperatures of between 80° and 200° C. for a time sufficient to obtain a still formable product.
Claim 9
Dependent Claim
73 words
Solution of curable resin as claimed in claim 1 in an inert organic solvent selected from dimethylformamide, dimethylacetamide, N-methyl pyrrolidone, tetramethyl urea, acetone, methylethyl ketone, methylisobutyl ketone, cyclohexanone, methylene chloride, ethyl chloride, 1,2-dichloroethane, dioxane, tetrahydrofuran, ethyl glycol, ethyl acetate, ethyl glycol acetate, methyl glycol acetate, diethyleneglycol diethyl ether, diethyleneglycol monoethyl ether acetate and mixtures thereof in which the resin is present in a concentration of 25 to 65% of the solution by weight.
Claim 10
Dependent Claim
33 words
Crosslinked polymer derived by heating the curable resin mixture of claim 1 or the prepolymers of claim 7 to temperatures of between 80° and 400° C. for a time sufficient to complete cure.
Claim 11
Dependent Claim
24 words
Fibrous material impregnated with curable resin as claimed in claim 1, prepolymer as claimed in claim 7 or solution as claimed in claim 8.
Claim 12
Dependent Claim
12 words
Film cast from solution of curable resin as claimed in claim 8.
Claim 13
Dependent Claim
33 words
Moulding composition comprising a curable resin as claimed in any one of claims 1 to 6 or prepolymer as claimed in claim 7 and additives selected from fillers, colourants, softeners or flameproofing agents.
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) | 1991-12-06 | 1992-06-06 | 1992-12-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-12-06 | 1996-06-06 | 1996-12-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-12-06 | 2000-06-06 | 2000-12-06 | $7700.00 | Window Closed / Lapsed |