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Umted States Patent [19] [111 4,303,779 Stenzenberger [45] Dec

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Umted States Patent [19] [111 4,303,779 Stenzenberger [45] Dec Umted States Patent [19] [111 4,303,779 Stenzenberger [45] Dec. 1, 1981 [54] THERMOSETTING IMIDE RESINS FROM Primary Examiner-—-Harold D. Anderson DIHYDRAZIDE Attorney, Agent, or Firm—Schwartz, Jeffery, Schwaab, [75] Inventor: Horst Stenzenberger, Schriesheim, Mack’ Blumemhal & Koch Fed. Rep. of Germany [57] ABSTRACT [73] Assignee: Technochemie Novel imide resins are prepared by reacting a mixture GmbH-Verfahrenstechnik, of a bisimide of an unsaturated dicarboxylic acid and a Dossenheim, Fed. Rep. of Germany monoimide with a dihydrazide of a dicarboxylic acid, [211 App]. NO; 97,657 preferably in an organic solvent or diluent at elevated temperature for a period of time insufficient to yield an [22] Fi1ed= Nov- 27, 1979 insoluble, infusible, fully cured imide resin. Solutions of [51] Int. Cl.3 ............................................ .. C08G 73/12 the resulting prepolymerilation PrOduCt are Stable at [52] US. (:1. ............................... .. 528/312; 428/473.5; room temperature and their viseeeity remains substan 525/422; 528/170; 528/210; 528/211; 528/321; tielly unchanged for a prolonged period of time- Fully 528/322 cured imide resins and articles thereof of a high heat [58] Field of Search ............. .. 528/322, 170, 312, 315, resistance are obtained by heating said prepolymerized 528/321, 210, 211; 525/422 imide resin or materials such as ?bers, metal wire webs, . and others im re nated therewith, if desired, in the [56] References Cited presence of curringgcatalysts, inhibitors, ?llers and other US PATENT DOCUMENTS materials to curing temperature up to 350° C. 3,562,223 2/1971 Bargain et al. .................... .. 528/322 4,211,860 7/1980 Stenzenberger .................. .. 528/322 17 Claims, N0 Drawings ‘4,303,779 1 2 are mixed with the bisimides and this mixture is reacted with a dicarboxylic acid dihydrazide of the general THERMOSETTINGDIl-IYDRAZIDE IMIDE RESINS , , . formula III _ 1~ BACKGROUND OF THE INVENTION A‘ 5 1. Field of the Invention , , , The present invention relates to novel ‘and highly advantageous thermosetting imide resin‘s, to a process of The reaction is carried out in such a manner thatthe producing such imide resins, to compositions and meth molar ratio between the imide groups in the mixturejand ods of using same and to articles made therewith. the hydrazide groups in the mixture, , 2. State of the Prior Art _ I i a It is known that the ethylenic double bond of maleic Number of Moles of Unreacted Imide acid imides is readily reacted with basic organic com Number of Moles of Acid I-Iydrazide pounds and especially, with organic arnineswhereby , aspartic acid imides are'foyrmed. This mode of reaction are between 1.1 and 100. The‘ fully unreacted monomer has been used, for instance, forproducing polymeriz mixture contains no free hydrazide groups and poly able imide resins. US. Pat. No. 3,562,223 describes said merizes under heating conditions, for example, between reaction and the reaction products. According to said 100° to 350° C. to a highly crosslinked polyimide resin patent, the speed of reaction is determined ‘to a far having high thermal stability. Accordingly, the novel reaching extent by the basicity of the amino compound. thermosetting imide resins of the present invention are It is also known that the ethylenically unsaturated obtained by reacting: A. a mixture of an N,N'-bisimide of an unsaturated double bond of bis-maleimides'canbe reacted with di dicarboxylic acid of the general formula I " " > carboxylic acid hydrazide to ‘form ‘a thermosetting 25 imide resin. West German Pat. No'. P 27 54 631.2 teaches such a reaction wherein the polyimide can be oII II 01 polymerized upon heating to a highly crosslinked poly- ' c c imide having hightemperature ‘stability. _ _ B N-A-N B 30 \ / \ / SUMMARY OF .THE'INVENTION" I . c c II II It is one object of the presentinvention to provide o novel .and "highly-advantageous thermosetting imide resins having improved flow properties. ‘ i' i A I _ ' Another object of the present invention to provide 35 a ‘simple and effective process of producing such ther mosetting imide resin_s._ H I _ - _ r . 0: Still another object of the present-invention is to provide a simple and effective method of polymerizing and hardening the prepolymerization products obtained according to thepresent invention. - ' r i A further object of the present invention is- to provid articles such as molded articles or coated ?ber materi wherein A represents a divalent organic-radical with at als, ‘webs, ?laments, rovings and the like. 45 least two carbon atoms, E _ represents a monovalent Other objects of the present invention and advanta radical with at least one carbon atom and B represents 'geous features thereof will become apparent as the de a divalent organic radical selected from the group con scription proceeds. ' ' ' i sisting of the following radicals .. The present vinvention relates to novel thermosetting imide resins obtained by the reaction of two compo H CH CH CH nent's, component A, a mixture of N,N’-bisimide of an ’ -\ / \3 / \3 ‘/ ~€ _/ C C C ‘C unsaturated dicarboxylic acid of a speci?c formula and "-1 ll " II’ I a monoimide of a speci?c formula and component B, c . c , c », H20 / \ / \ / \ ,\ the dihydrazide of an organic dicarboxylic acid of a H CH3 H ‘ _ speci?c formula, The' invention also relates to the pro cess for producing'the thermpsettingjmide resinsf _ with ' ' It has, therefore, been discovered that new thermo B. the dihydrazide of an organic dicarboxylic acid of setting imide resins with ‘optimal flowt'properties can be the general formula III ' ‘ -' obtained when vmonoiinides of the generalv forrnula_.II V 60 ,. O . .|l,,-_ C / \ " ‘ .B ' N-E. wherein‘ D-represents a divalent organic radical. \ :/ is. 65 The group, designated by, A ‘in__,_l_?orrnula I can be an . C , alkylene group with 2 to 12 carbon atoms, a cycloal ll ' I 0 kylene group with 5 or 6 carbon atoms, a heterocy clic group with 4 or 5 carbon atoms, and at least one 14,303,779 3 nitrogen, oxygen‘, ‘or sulfur atom ih'the heterocyclic N-dodecylmaleimide,_ , ,_ ring, . _ ‘ ._,> ,i 1,, .‘ ‘Y N-is‘obutylm‘aleimide, -“'- I a mono- or dicarbocylic group, or ‘ I N-isopropylmaleimide, " at least two mono- or dicarbocylic aromatic or cycloal N-phenylmaleimide, kylene groups which may be linked to each other by LII N-ph'enylc'itroconimide, a carbon to carbonbond or‘ N-phenylitaconimide, by a divalent group such as wN_-toluylmaleimide, oxygen, N-rnono-chlorophenylmaleimide, sulfur, N-biphenylmaleimide ‘ ' ' alkylene with l to 3 carbon atoms, or one of ‘the fol N-napthylmaleimide lowing groups: ' N-vinylrnaleimide ' N-allylmaleimide, and N-cycl'ohexylmaleimide. ' ' The divalent unsaturated group B of the general for 15 mula II is identical ‘as that in" general formula I. ' In general‘ formula III, B represents a divalent or ganic group such as an alkylene group, a cycloalkylene group and arylene group and the like. Suitable dicarboxylic acid dihydrazides‘ are, for in 20 stance, the following compounds: . ' ' ‘ oxalic acid dihydrazide, 'malonic acid dihydrazide, succinic acid dihydrazide, - glutaric acid dihydrazide, adipic acid dihydrazide,: pimelic acid dihydrazide, suberic. acid dihydrazide, .. seba'cic acid dihydrazide, . cyclohexane dicarboxylic and dihydrazide, 30 terephthalic acid dihydrazide, - isophthalic acid dihydrazide, 2,6-naphthalene dicarboxylic acid dihydrazide, 2,7-'naphthalene dicarboxylic acid dihydrazide, v and others. Mixtures of ‘two or more of the above-men tioned dicarboxylic acid'dihydrazides can also be‘used. The production of new, thermosetting, imide resins In said groups, the substituents R1, R2, R3, R4, and having excellent ?ow characteristics is effected, for R5, are alkyl with l to 5 carbon atoms. example,‘ by intimately mixing the'initial materials by Bisimides which have proven to be of special value using conventional methods of the mixing and grinding for preparing the novel imide resins are: of powders and heating them subsequently to tempera 1,2-bismaleimido ethane, tures between 80° and 180° C. until a product that is still 1,4-bismaleimido butane, plastic or possibly still soluble, is formed. The progress 1,6-bismaleimido hexane, of the prepolymerization has the effect that the initially l, l2-bismaleimido dodecane, low viscosity melt of the monomer mixture becomes l,6-bismaleimido-(2,2,4~trimethyl)hexane, '45 steadily thicker and ?nally solidi?es. Such a solidi?ed 1,3-bismaleimido benzene, " ' 7 or highly viscous melt may still be dissolved in high l,4-bismaleimido benzene, boiling solvents such as N-methylpyrrolidone, dimeth 4,4’-bismaleimido diphenyl methane, ylacetamide, dimethylformamide, tetramethylurea or 4,4’-bismaleimido diphenyl ether, their mixtures and used in the preparation of glass fabric 4,4’-bismaleimido diphenyl sul?de, 50 preimpregnates (referred to hereinafter as prepregs). 4,4’-bismaleimido diphenyl sulfone, ’ _ The extent to whichthe prepolymerization is taken 4,4-bismaleimido dicyclohexyl‘methane, depends essentially on the intended application of the 2,4-bismaleimido toluene, thermosetting polyimide prepolymer. For ‘processing 2,6-bismaleimido toluene, byv lmeans ofv ‘injection molding, melt viscosities of N,N’-m-xylylene bismaleimide, 55 500-2500 centipoises are advantageous, while for pro N,N'-p-xylylene bismaleimide, cessing with ‘solvents, highly‘ viscous resinslare also N,N’-m-phenylene biscitraconic acid imide, suitable. ' ' ' ‘ N,N‘-4,4'-diphenylmethane citraconimide, 'The new thermosetting imide resins may also be pre N,N’-4,4'-diphenylmethane bisitaconimide, pared in inert organic solvents, for example, dimethyl and others. Mixtures of the above-mentioned bisimides 60 formamide, dimethylacetamide, N-methylpyrrolidone, can also be used for producing the imide resins accord tetramethylurea of mixtures thereof. This is done pref ing to the present invention. ' " ' erably whenever further processing requires the use of In the general formula II, E can represent an alkyl a solution. Low boiling solvents, such as tetrahydrofu group, a cycloalkyl group and an aryl group.
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