JPH0439483B2 - - Google Patents

Description

[Detailed description of the invention]

Presentation of Related Applications This application is filed under U.S. Patent Application No.
No. 459442 (filed on January 20, 1983; U.S. Patent No.
4518788). BACKGROUND OF THE INVENTION Bismaleimides have been used with epoxy monomers and aromatic amines to form high heat distortion temperature polyimide molding compositions, such as those disclosed in U.S. Pat. Nos. 4,294,723 and 4,294,877. There is. A particular disadvantage of these molding compositions is their slow cure rate, with typical curing times of approximately
It takes 0.5 to 2 hours. The rapid reaction of maleic anhydride with aliphatic vinyl ethers has been shown in Vinyl and
Diene Monomers, Vol.24.Part I, pp.399−
401 (New York, Wiley Interscience, 1970)
It is well known as disclosed in 2010). However, cured products obtained from maleimides and aliphatic vinyl ethers have low heat distortion temperatures and are therefore not useful. Moreover, these aliphatic vinyl ethers are liquid at room temperature and are not compatible with the formulation of solid molding compositions, making it difficult to process such compositions into final products. The present invention was made based on the discovery that maleimide rapidly copolymerizes with aromatic vinyl ether. The resulting copolymers have high oxidative stability and high heat distortion temperatures, overcoming the shortcomings inherent in polyimide molding compositions known in the art. Disclosure of the Invention The present invention provides a molding composition containing an aromatic vinyl ether and a maleimide. A suitable molding composition has the following formula: (A) aromatic vinyl ether of (B) and the following formula: has one or more chemical bonding units, and has a molecular weight of 111~
Contains maleimide in the range of approximately 5000. In the formula, R ¹ is an alkylene group having 1 to 8 carbon atoms, R ² , R ³ and R ⁴ are selected from the group consisting of hydrogen and an alkyl group having 1 to 8 carbon atoms, and R ⁵ and R ⁶ is selected from the group consisting of hydrogen, halogen and alkyl groups having 1 to 8 carbon atoms, G is -O-, A is phenylene,
Tolylene, xylylene, naphthylene, biphenylene, anthrylene, following formula: selected from the group consisting of polyvalent aromatic groups from the group consisting of diarylene groups, and Q is of the following formula: -S-, -
O-, _SO2- ,

【formula】

and n is 2. Examples of maleimides suitable for use in the molding compositions of the present invention are described in the US patents to Holub, listed below. No. 3558741 and No. 3787439 (maleimide-substituted organopolysiloxane), No.
No. 3652716 and No. 3729446 (maleimide-substituted polyester), No. 3689464 and No. 3763273 (maleimide-substituted polyamide) and No. 3576031 (maleimide-substituted organosilane). All of these patents are assigned to the applicant. Other suitable maleimides include the formula: bismaleimide and the following formula: monofunctional maleimide. ^R5 here
and R ⁶ is hydrogen, halogen and 1 carbon atom
~8 alkyl groups, where X is a divalent hydrocarbon group having 1 to 35 carbon atoms and the following formula: selected from the group consisting of divalent groups, Z is a hydrocarbon group having up to 15 carbon atoms, -S-, -O-, _-SO2
-,

【formula】

[expression] and

[Formula] is a divalent group selected from the group consisting of, R ⁷ is a monovalent alkyl group having 1 to 6 carbon atoms, and Y is an aliphatic group having 1 to 8 carbon atoms and a carbon atom. Number 6-20
is a monovalent hydrocarbon group selected from the group consisting of aromatic groups. To form a type of bismaleimide, the formula
A diamino compound of _NH2 -X- _NH2 (wherein X is as defined above) is reacted with maleic anhydride to form maleamic acid. Maleamic acid is treated with a mixture of acetic anhydride and a catalyst composition such as nickel acetate and triethylamine to produce the corresponding bismaleimide. Certain monofunctional maleimides can be formed in a similar manner, using an amine of the formula _NH2 -Y, where Y is a monovalent group as previously described, and maleic anhydride to form maleamic acid. In addition to bismaleimides and monofunctional maleimides, maleimide oligomers of the following formula are also suitable for use in the molding compositions of the invention. Here, X, R ⁵ and R ⁶ are as defined above,
X′ is selected from the same group of divalent organic groups as X;
m is an integer from 1 to 10. To prepare these oligomers, a condensation reaction of bismaleimide with a diamine of the formula _NH2 -X'- _NH2 , where X' is selected from the group of divalent radicals described above, is carried out. A stoichiometrically insufficient amount of diamine is used to prevent complete polymerization of the bismaleimide. The above maleimide monomer and oligomer are
Just as the organic groups represented by X, X' and Y present therein can vary within a wide range. Among the divalent groups represented by X and ,
Examples include propylene, butylene, isopropylidene, hexylene, cyclohexylene, and neopentylene. Among the divalent groups X and X' are the formula -CH ₂
Divalent groups of _-CH2 -O- _CH2 - _CH2- are included. Among the divalent aromatics within X and X' are, for example, m-phenylene, p-phenylene,
2,6-naphthylene, 2-methyl-1,3-phenylene, dichlorophenylene and diaryl groups, such as P,P'-biphenylene, m,m'-biphenylene, diphenylenemethene, diphenylene oxide, These include diphenylene sulfone, diphenylene sulfide, and ketobiphenylene. These diaryl groups may be attached to both nitrogens in the ortho, meta or para position. X and X' are preferably and its alkyl-substituted derivatives having up to 35 carbon atoms. Representative examples of bismaleimides which can be used in the molding compositions of the invention or which can be converted into oligomers include, for example: N,N'-1,2-ethylene-bismaleimide, N,N'-methylene-bismaleimide, N,N'-1,4-butylene-bismaleimide, N,N'-1,6-hexamethylene- Bismaleimide, N,N'-1,4-phenylene-bismaleimide, N,N'-1,3-phenylene-bismaleimide, N,N'-2-methyl-1,3-phenylene-bismaleimide, N , N'-4,4'-diphenylmethyl-bismaleimide, N,N'-4,4'-diphenyl ether-bismaleimide, N,N'-4,4'-diphenylsulfone-bismaleimide, N, N'-4,4'-diphenyl sulfide-bismaleimide, N,N'-4,4'-dicyclohexylmethane-bismaleimide, N,N'-1,3-xylene-bismaleimide, N , N'-4,4'-benzophenone-bismaleimide, N,N'-(3,3'dichloro-4,4'-biphenylene)bismaleimide. The bismaleimides listed above are typically prepared by reacting 1 mole of a diamino compound with the corresponding divalent group X with 2 moles of maleic anhydride. Other anhydrides, such as substituted maleic anhydride, can also be utilized in the preparation of bismaleimides. For example, citraconic anhydride and pyrosinconic (also known as dimethylmaleic) anhydride can be used with 4,4'-diaminodiphenylmethane to produce bismaleimides, specifically N,N'-4,4'-
Diphenylmethane-bis(methyl-maleimide)
and N,N'-4,4'-diphenylmethane-bis(dimethylmaleimide).
Mixtures of anhydrides and/or mixtures of diamino compounds can be used to prepare mixtures of bismaleimides. Mixtures of such bismaleimides are suitable for use in the molding compositions of the present invention and for producing oligomers suitable for use in the present invention. Halogenated bismaleimides, i.e. divalent groups X and X′ or monovalent groups R ⁵ and
Bismaleimides with halogen present on ^R6 are also
It can be used without departing from the gist of the present invention. For example, N,N'-(3,3'dichloro-4,
4′-diphenyloxy-bismaleimide), N,
N'-(3,3'dibromo-4,4'-diphenylmethane)-bismaleimide and the like are suitable as maleimides for use in the molding composition of the present invention. Monofunctional maleimides can also vary within a wide range, depending on the organic groups present therein. Y
Particularly preferred among the monovalent groups represented by are monovalent saturated alkyl groups having, for example, straight-chain and branched structures and having up to 8 carbon atoms. Suitable alkyl groups include, for example, methyl, ethyl, propyl, butyl, isopropyl, pentyl, hexyl, and the like. The monovalent group represented by Y also includes an aromatic group having 6 to 20 carbon atoms. Included in this group are, for example, phenyl, 3-methylphenyl, naphthyl,
Such as bisphenyl. The aromatic vinyl ethers of the molding compositions according to the invention can vary within a wide range, since a large number of different aromatic units can be present therein. Some of the vinyl ether monomers suitable for the molding compositions of the present invention are disclosed in Crivello, U.S. Pat.
(U.S. Pat. No. 4,518,788).
Some of the aromatic polyvinyl ether monomers within the scope of the present invention are defined in detail below. Aromatic vinyl ethers suitable for use in the present invention also include aromatic vinyl ethers having only one vinyl ether moiety. A in the formula is phenylene, tolylene, xylylene, naphthylene, biphenylene, anthrylene,
The following formula: selected from the group consisting of polyvalent aromatic groups from the group consisting of diarylene groups, and Q is of the following formula: -S-, -
O-, _-SO2- ,

【formula】

selected from the group consisting of divalent radicals of the formula and alkylene radicals having 1 to 8 carbon atoms. Suitable aromatic vinyl ethers also vary with the groups present on the vinyl ether group. Divalent radicals included within R ¹ in the formula are alkylene radicals having 1 to 8 carbon atoms, such as methylene, ethylene, trimethylene, tetramethylene, and the like. Groups within R ² , R ³ and R ⁴ are, for example, hydrogen, monovalent alkyl groups having 1 to 8 carbon atoms, such as methyl, ethyl, propyl and the like. Also included within the scope of A are halogenated derivatives of the above-mentioned aromatic groups, such as chlorophenylene, bromotrilene, chlorophenyl, bromophenyl, and the like. Specific examples of aromatic polyvinyl ethers of the formula include: One way to form some of the aromatic vinyl ethers of the formula is by condensing an aryl hydroxide or alkali metal salt of a carboxylic acid with a haloalkyl vinyl ether in the presence of dimethyl sulfoxide as shown in the following reaction scheme: be. A(GM) _o +nBR ¹ OC(R ⁴ ) = C(R ² )(R ³ ) → Formula where A, G, R ¹ , R ² , R ³ and R ⁴ and n are as defined above, B is a halogen group, and M is an alkali metal ion. Once the desired aromatic vinyl ether and maleimide compound are obtained, a molding composition can be obtained by melt-mixing these two components at a temperature of about 110° C. or lower. In addition to maleimide compounds and aromatic vinyl ethers, the molding compositions may contain peroxides or azo catalysts in order to lower the required curing temperature or shorten the curing time. Typical organic peroxides suitable for obtaining catalytic action include, for example, ketone peroxides, peroxy acids, dibasic acid peroxides, aldehyde peroxides, alkyl peroxides, hydroperoxides, alkyl peroxy esters, Peroxide derivatives, specifically t-butyl peroxypivalate, 2,4-dichlorobenzoyl peroxide, caprylyl peroxide,
lauroyl peroxide, decanoyl peroxide, propionyl peroxide, acetyl peroxide, t-butyl peroxy isoptylate,
p-chlorobenzoyl peroxide, benzoyl peroxide, hydroxyheptyl peroxide, cyclohexanone peroxide, 2,5-dimethylhexyl-2,5-di(peroxybenzoate), di-t-butyl diperphthalate, t
-butyl hydroperoxide, di-t-butyl peroxide, methyl ethyl ketone peroxide,
P-methane hydroperoxide, cumene hydroperoxide, 2,5-dimethylhexyl-2,5
-dihydroperoxide, t-butyl-hydroperoxide, peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, and the like. In addition to these organic peroxides, certain azo compounds are also suitable as catalysts for the molding compositions of the invention. Such azo compounds include azobisalkylnitrile and azo compounds of the formula:

【formula】

【formula】

[Formula] (C ₆ H ₅ ) ₃ C-N= N-C (C ₆ H ₅ ) ₃ ,

【formula】

[formula] etc.; and kino types, e.g.

【formula】

【formula】

【formula】

[Formula] etc. In addition to catalysts, the molding compositions can also contain fillers, such as clay, silica, calcium carbonate, aluminum trihydrate, carbon black, talc, calcium sulfate, wollastonite, and the like. Suitable weight ratios of filler to active ingredient range from 0 to 300 parts filler per 100 parts active ingredient. These molding compositions may also contain other additives, such as antioxidants, flame retardants, impact modifiers, etc. Once the molding composition has been prepared by melt mixing the aromatic vinyl ether and maleimide compounds together with the desired additives, the temperature is increased from 140° to about 170°C.
The molding composition is cured by raising the temperature to .degree. Application of such temperatures results in rapid polymerization. This heat-activated polymerization is usually carried out in a mold under pressure. Such pressure is about 200 to about 600Psi
can be in the range of Cure times typically range from about 1 to 4.5 minutes. Although this polymerization is rapid without catalyst at relatively low temperatures, the addition of peroxide or azo catalysts as described above can lower the curing temperature or shorten the curing time. Cure times for molding compositions containing such catalysts are typically reduced to a range of about 1 to 2 minutes. This allows the polyimide molding composition of the present invention to be used as a photocurable coating and as a photoresist. Photo-initiated curing is
This can be accomplished by adding a conventional free radical photoinitiator, such as butyl benzoin ether, to the mixture of aromatic vinyl ether monomers and maleimide monomers. Photoinitiated curing, for mixtures containing the butyl benzoin ethers described above, involves placing the molding composition at a distance of 6 inches from a mercury arc lamp.
This can be achieved by irradiating for 30 seconds.
If photoinitiated curing is desired, it is preferred to use a maleimide monomer with a low melting point to increase solubility with the aromatic vinyl ether at room temperature. An alternative to mixing the maleimide compound and the aromatic vinyl ether monomer as described above is to dissolve both the aromatic vinyl ether monomer and the maleimide compound in a common organic solvent, such as acetone;
This method involves impregnating a fiber matrix, such as glass fiber cloth, with this solution. The organic solvent is then removed from the fiber matrix to obtain a dry fiber matrix impregnated with a maleimide compound and a vinyl ether monomer (hereinafter referred to as "blebreg"). These bleb legs are cut, stacked, and heated to initiate polymerization. Suitable curing temperatures range from about 140° to about 170°C. These blemish legs at such curing temperatures are approximately
They can be molded by pressing together at a pressure of 400-600 Psi for about 2-3 minutes. An alternative to curing a molten mixture consisting essentially of maleimide and aromatic vinyl ether is to granulate and pelletize the mixture to produce a solid thermoset composition for injection molding, compression molding and transfer molding. be. Optimum crosslinking density is obtained with a 1:1 molar ratio of maleimide having two or more electrically deficient groups, e.g. bismaleimide, to aromatic vinyl ether having two or more vinyl groups, e.g. aromatic bisvinyl ether. It is from a molding composition. However, the stoichiometry of the molding composition may vary within wide tolerances, and the ratio of maleimide functional groups to vinyl groups of the formula may range from about 0.25 to about 4. A suitably cured composition is obtained. The mechanical properties of the cured molding composition can be varied to desired values by varying the stoichiometry of the molding composition and by varying the components of the molding composition. For example, when high bending strength and elongation are desired, maleimide oligomers are more suitable than maleimide monomers. Flexural strength, elongation and tensile strength can be varied by varying the stoichiometry. Preferably, the curing temperature is in the range of about 140° to about 170°C. Higher temperatures are also suitable, but such high temperatures can lead to unwanted decomposition of the aromatic vinyl ether or additives present in the molding composition. The curing time at temperatures in the above range varies from 1 to
It varies within a range of 4.5 minutes. The cured molding composition typically has a high heat distortion temperature of about 220° C. and suitable engineering properties, such as percentage elongation, tensile strength, tensile modulus, flexural strength, and the like. The following experimental procedures were used to produce selected components of the particular thermoplastic compositions that make up the present invention. These procedures are presented to assist in practicing the invention and are not intended to limit the invention. To produce N,N'-4,4'-diphenylmethane bismaleimide, 0.25 moles of 4,4'-diaminodiphenylmethane and 0.5 moles of maleic anhydride were added to 1 part of acetone. A rapid reaction occurred to form a precipitate of bismaleamic acid. Next, 0.5 moles of triethylamine, 0.02 moles of nickel acetate and 2.5 moles of acetic anhydride were added.
After the mixture was refluxed for 2.5 hours, the entire amount of bismaleamic acid was dissolved and the reaction mixture was poured into an equal volume of water. The product separated as an oil, which was crystallized in an ice bath and purified by two recrystallizations from toluene. Yield before recrystallization is 65-80% of theoretical value
It was hot. The following formula: of divinyl ether, 68.5 g bisphenol A, 500 ml toluene and 100 ml
24g of NaOH dissolved in water was added to the 1000ml flask. The flask was equipped with a paddle stirrer, reflux condenser, Dean Stark trap, and nitrogen inlet tube. The reaction mixture was heated to reflux and the water formed was collected in a trap and removed from the reaction. Reflux was continued until no more water was collected, then the trap was replaced with a special Dean Stark trap containing activated molecular sieves. Refluxing was continued overnight to thoroughly dry the system. The reaction mixture was then filtered to recover bisphenol A disodium salt. 2000ml of this salt
Transferred to a flask and added 1 part of dimethyl sulfoxide. This reaction mixture was heated to approximately 60°C and 65 g
of 2-chloroethyl vinyl ether was slowly added. The reaction mixture was then stirred at 60°C for 1 hour.
Cool and stir for another 5 hours at room temperature, then
Pour into 1000ml 50% NaOH. An oil separated and was collected. 3 more times the oil with 50% NaoH aqueous solution
Unreacted bisphenol A was removed by washing twice.
The washings were extracted with ether and the extract was added to the oil.
Evaporation of ether yields divinyl ether
Obtained in 77g (yield 69.8%). The following formula: To produce the aromatic divinyl ether of
632.76 g (2 mol) bisethoxylated bisphenol A (Dianol-22, manufactured by AKZO Chemie), 300 ml
of toluene and 459.2 g (6 moles) of allyl chloride were stirred until the bisethoxylated bisphenol A was dissolved. Next 240g
(6 mol) of solid NaOH was added and stirring continued for 0.5 h. Next, add 32g (0.1 mol) of tetrabutylammonium bromide and reduce the stirring to 0.5
Lasted for an hour. The temperature of the reaction mixture was slowly raised to 50°C, after which an exothermic reaction occurred and the reaction temperature rose to 100°C. The temperature of the reaction mixture was brought to 75°C in a water bath and stirred overnight (16 hours). The product was isolated by pouring the reaction mixture into 2 distilled water and separating the organic layer using a separatory funnel. After washing the organic layer three times with 500 ml each of water, it was dried over solid sodium sulfate and the toluene was removed under vacuum to yield 690 g (86% of theory) of bisallyl ether product. Rucl ₂ (PPh ₃ ) 3 0.96 g (1 mol) to 396.5 g (1 mol) of bisallyl ether _of ethoxylated bisphenol A
×10 ^-3 mol) was added. The reaction mixture was slowly heated to 120°C in a silicone oil bath and maintained at this temperature for 1.5 hours. After cooling, the product was examined by nuclear magnetic resonance (NMR) and was found to be completely isomerized to bispropenyl ether. The product was a mixture of three bispropenyl ether isomers (cis-cis, cis-trans, trans-trans). The following examples are intended to specifically illustrate the present invention, but are not intended to limit the invention. All parts are by weight unless otherwise specified. EXAMPLE This example specifically describes the production of one example of the molding composition of the present invention and its curing method. The following materials were heated and mixed together at 80°C until homogeneous. The 2-part t-butylberbenzoate mixture was allowed to cool and solidify. Grind this to 100
Part of silica (CEM241, Combustion
Engineering) and dry blended. This mixture was further mixed on a two roll mill at 80°C and allowed to set. 12 tons of solid molding compound
600Psi, 160℃ on Hull transfer molding press,
Transfer molding was performed for 2 minutes. The obtained test material exhibited a heating deformation temperature of 200°C or higher at 264 Psi. The mechanical properties are shown in Table 1.

[Table] Example This example specifically describes a method for producing and curing one example of the molding composition of the present invention. The following materials were placed in a large beaker. 1 part t-Butylberbenzoate The mixture was heated and stirred at 80°C until homogeneous, then 120 parts of silica (CEM421) were added and mixing continued until a homogeneous blend was obtained. A molding compound of the consistency of flour dough was obtained, which was transfer molded as described in the examples. Bars and discs were obtained, and the heating deformation temperature was 180°C. EXAMPLE This example illustrates an alternative method of curing one example of the molding composition of the present invention. The example was repeated except for the silica filler. 80
After the mixture was made homogeneous by stirring at °C, it was used to impregnate a glass cloth. The impregnated fabric was cut into 6 inch x 6 inch square pieces and the 7 square pieces were stacked together to create a bleb reg. 500Psi, 160 bleb reg in Carver press
A cured laminate was obtained after pressing at 0.degree. C. for 2 minutes. EXAMPLE This example specifically describes a method for producing and curing one example of the molding composition of the present invention. The following ingredients were mixed at 80°C using the procedure in the example. 1 part of t-butylberbenzoate The mixture was then powder blended with 120 parts of silica (CEM421) and milled at 80°C. The hardened molding compound was then transfer molded to obtain a molded article as described in the Examples. The heating deformation temperature was 200°C or higher. EXAMPLE This example illustrates the effect of various radical initiators on resin gelation time. Equimolar amounts of the following materials were heated and mixed together at 150° C. using 2% by weight of various radical initiators. Gel times for five mixtures using the radical initiators listed in Table 1 were measured using a Sunshine Gel meter equipped with a constant temperature bath maintained at 150°C.
The gelation time measurements and initiator half-life are shown in the table.

[Table] Inzoate Example This example specifically describes a method for photocuring one example of the molding composition of the present invention. 3.58 g (0.01 mol) N,N'-bismaleimide
4,4'-diphenylmethane and 3.10 g (0.01 mole)
0.13 g (3% by weight) of N-butyl benzoin ether (benzoin n-butyl ether) was added to the bisphenol A-bispropenyl ether. The mixture was warmed slightly to create a homogeneous solution and then spread as a 2 mil film onto a glass plate using a drawbar. The film was irradiated with a medium pressure mercury arc lamp at a distance of 6 inches for 30 seconds.
A crosslinked insoluble film was obtained. Where a mask was placed on the film before irradiation, a negative image of the mask was obtained when the film was washed with acetone after irradiation. Although the above embodiments show various modifications of the present invention, it is clear that those skilled in the art can conceive of further various modifications according to the above teachings without departing from the gist of the present invention. .

Claims (1)

[Scope of Claims] 1. A molding composition comprising the following components A and B, to which a filler of 60% by weight or less based on the weight of the molding composition is optionally added: Formula A () aromatic vinyl ether Maleimide having one or more chemical bonding units of formula B () and having a molecular weight in the range of 111 to 5000 (R ¹ in the formula is an alkylene group having 1 to 8 carbon atoms, R ² , R ³ and R ⁴ are selected from the group consisting of hydrogen and an alkyl group having 1 to 8 carbon atoms, and R ⁵ and R ⁶ is selected from the group consisting of hydrogen, halogen and alkyl groups having 1 to 8 carbon atoms, G is -O-, and A is phenylene, tolylene, xylylene, naphthylene, biphenylene, anthrylene, of the formula: selected from the group consisting of polyvalent aromatic groups from the group consisting of diarylene groups, and Q is of the following formula: -S-, -
O-, -SO ₂ -, divalent groups of the formula [formula] and alkylene groups having 1 to 8 carbon atoms, where n is 2). 2. The molding composition according to claim 1, which contains an effective amount of a thermosetting catalyst. 3. The molding composition according to claim 2, wherein the thermosetting catalyst is selected from the group consisting of organic peroxides and azo compounds. 4. The molding composition according to claim 2, wherein the thermosetting catalyst is selected from the group of organic peroxides consisting of t-butyl perbenzoate, t-butyl hydroperoxide, benzopinacol and benzoyl peroxide. 5 The above maleimide has the following formula: The molding composition according to claim 1, which is bismaleimide (in the formula, R ⁵ and R ⁶ are hydrogen,
Halogen or C _1-8 alkyl group, X has 1 carbon atom
~35 divalent hydrocarbon groups and the following formula: selected from the group consisting of divalent groups, Z is a hydrocarbon group having up to 15 carbon atoms, -S-, -O-, _-SO2
-, [Formula] [Formula] and [Formula], and R ⁷ is a monovalent alkyl group having 1 to 6 carbon atoms). 6 The divalent group X of the above bismaleimide is and alkyl-substituted derivatives thereof having up to 35 carbon atoms.
The molding composition described in . 7 The above maleimide has the following formula: The molding composition according to claim 1, wherein R ⁵ and R ⁶ are hydrogen, halogen, or a C _1-8 alkyl group, and X and
~35 divalent hydrocarbon groups and the following formula: selected from the group consisting of divalent groups, Z is a divalent hydrocarbon group having up to 15 carbon atoms, -X-, -O-, -
is a divalent group selected from the group consisting of SO ₂ −, [Formula] [Formula] and [Formula], R ⁷ is a monovalent alkyl group having 1 to 6 carbon atoms, and m is 1
is an integer between ~10). 8. The molding product according to claim 1, wherein the maleimide is N,N'-4,4'-diphenylmethane bismaleimide or N,N'-6-methyl-1,3-phenylene bismaleimide. Composition. 9 The aromatic group A of formula 1 is or expression The molding composition according to claim 1, which is a diarylene group (wherein Q is an alkylene group having 1 to 8 carbon atoms). 10 The above aromatic vinyl ether has the following formula: and The molding composition according to claim 1, wherein the molding composition is selected from bisvinyl ethers. 11. The molding composition according to claim 1, wherein the molar ratio of maleimide to aromatic vinyl ether is within the range of 0.25 to 4. 12. The molding composition of claim 1, wherein said filler is selected from the group consisting of clay, silica, calcium carbonate, aluminum trihydrate, carbon black, talc, calcium sulfate and wollastonite. 13. A molding composition according to claim 1, wherein said filler is in the form of a fibrous matrix.