JPH02173065A - Thermosetting resin composition - Google Patents

Abstract

PURPOSE:To prepare a thermosetting resin compsn. excellent in impact strength and toughness by compounding a polyaminobismaleimide resin comprising N,N '-4,4'-diphenylmethanebismaleimide and an arom. amine resin with a glass fiber. CONSTITUTION:100 pts.wt. polyaminobismaleimide resin comprising 100wt.% N,N'-4,4'-diphenylmethanebismaleimide of formula I and 5-100wt.% arom. amine resin of formula II [wherein A is phenylene, alkyl-substd. phenylene, diphenylene, diphenyl ether or naphthylenyl; R<1> is halogen, hydroxyl, 1-4C alkoxy or 1-5C alkyl; R<1> may be the same or different from each other, and may form a ring; lis 1 or 2; m is 0-3; and n is 0-300] is compounded with 10-400 pts.wt. glass fiber to give a thermosetting resin compsn.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel thermosetting resin composition having excellent impact resistance and toughness.

[Prior Art] Thermosetting resins having an imide structure have been widely used in industry since they have excellent electrical insulation properties, heat resistance, and dimensional stability of molded products.

However, thermosetting resins made using aromatic bis-7-reimite have disadvantages in that they are insoluble and infusible and have excellent heat resistance, or they are poor in impact resistance and toughness.

Therefore, as a method for improving the 11i impact resistance and toughness of aromatic bismaleimide, there have been attempts to use aromatic diamines in aromatic bismaleimide6. For example, N
, N'-(4,4,'-methylene diphenylene) bismaleimide and 4,4°-diaminodiphenylmethane. Polyamino bismaleimide resin (manufactured by Loos-Boulin, trade name Kinel) has high impact resistance and toughness. Because it is superior to aromatic bismaleimide alone, it is widely used as molded products for structural members, sliding members, etc. However, these thermosetting resins have not yet been satisfactory in terms of impact resistance and toughness.

[Try to invent or solve. ffa1 An object of the present invention is to provide a thermosetting resin composition that has all the conventional heat resistance properties and also has excellent impact resistance and toughness.

[Means for Solving the Problem] As a result of intensive research in order to achieve the above object, the present inventors have discovered that polyamino bismaleimide resin made of a bismaleimide compound and aromatic amine resin and glass fiber of a specific We have completed the present invention by discovering that a thermosetting resin composition is particularly effective.

That is, the thermosetting resin composition of the present invention comprises N,N'-4,4°-diphenylmethane bismaleimide represented by the formula and an aromatic amine resin (■) represented by the general formula (n) (in the formula , A represents a phenylene group, an alkyl-substituted phenylene group, a diphenylene group, a diphenyl ether group, or a naphthylenyl group, and 1 (1 represents a halogen atom, a hydroxyl group, a lower alkoxy group having 4 or less carbon atoms, or a lower alkyl group having 5 or less carbon atoms) , and R1 may be the same or different from each other, and the 6 sentences that may form a ring represent 1 or 2, m represents an integer of θ to 3, and n represents an integer of 0 to 300. , ) is a thermosetting resin composition consisting of 100 parts by weight of a polyamino bismaleimide resin and 11 gk parts of glass fiber filO~400f.

The N,N'-4,4°-diphenylmethane bismaleimide represented by the formula (I) is prepared in 4. by a commonly known method.
It can be easily produced by a synthesis/dehydration reaction of 4'-diaminodiphenylmethane and maleic anhydride.

The aromatic amine resin represented by the general formula (11) used in the present invention has the general formula (IT) 820CH2-^-C11,011" (N)
Aralkyl represented by (wherein A represents a phenylene group, an alkyl-substituted phenylene group, a diphenylene group, a diphenyl ether group, or a naphthylenyl group, and R2 represents a hydrogen atom, an acyl group, or a lower alkyl group having 4 or less carbon atoms) With respect to 1 mole of alcohol derivative, the general formula (III) (wherein R1 represents a halogen atom, a hydroxyl group, a lower alkoxy group having 4 or less carbon atoms, or a lower alkyl group having 5 or less carbon atoms, and 11 are the same as each other) 0 represents 1 or 2, and 1m represents an integer from θ to 3, which may be different from each other and may form a ring. (Special application 1986)
2-252517) It is a new resin.

General formula (IT
), A is a n group, and R2 is a hydrogen atom, an acyl group or an alkyl group. -The compound represented by formula (IV) is specifically α,α'-dihydroxy-〇-xylene, α,α
'-dihydroxy-m-xylene, α,α゛-dihydroxy-p-xylene.

α, α゛-diacetoxy〇-xylene, α.

α°-diacetoxy m-xylene, α, α diacetoxy p-xylene, α, α°-cyprobionoxy P-
xylene, α, α-di-n-butyroxy-P-xylene, α, α-dimethoxy-0-xylene, α, α°
-dimethoxy m-xylene, α, α°-dimethoxy p-xylene, α, α°-jetoxy O-xylene, α.

α'-jetoxy m-xylene, α, α゛-jetoxy p-xylene, α, α-diisopropoxy-〇-
xylene, α, α°-diisopropoxy-m-xylene, α5α゛-diisopropoxy-2-xylene, α, α
゛-Di-n-propoxy p-xylene, α, α゛-di-n-butoxy m-xylene, α, α゛-di-n-butoxy p-xylene, α, α′-di-5ec-butoxy=ρ-xylene, α,α°-diisobutoxy p-xylene, 4.4°-dihydroxymethyldiphenyl ether, 4.4′-dihydroxymethyldiphenyl, 2.
6-dihydroxynaphthalene, 4,4°-diacetoxymethyldiphenyl ether, 4,4°-diacetoxymethyldiphenyl, 2,6-diacedoxymethylnaphthalene, 4,4°-methoxymethyldiphenyl ether, 4
．． 4'-Methoxymethyldiphenyl, 4.4'-jethoxymethyldiphenyl ether, 4,4'-dihydroxymethyldiphenyl, 4.4'-diisobutoxymethyldiphenyl ether, α,α°-dimethoxy 2-methyl-P-xylene, α, α′-dimethoxy-3-methyl-m=xylene, α, α°-dihydroxy-2,5-dimethyl-p-xylene, α, α″-dimethoxy 2.5
-dimethyl-p-xylene, α,α-dimethoxy-2
, 4-dimethyl-1,3-xylene, α.

α゛-dimethoxy-2,4-dimethyl-1,5-xylene and the like can be mentioned. Among them, the preferred compound is α
, α'-dimethoxy P-xylene.

Also, R1 in the general formula (m) representing an aromatic amine compound
is a halogen atom, a hydroxyl group, a lower alkoxy group with a JR prime number of 4 or less, or a lower alkyl group with a carbon number of 5 or less,
These are O~3(ll), which may be the same or different from each other, may form a ring, and have 1 or 2 amino groups. -The compound represented by the formula (m) is specifically Specifically, aniline, 0-toluidine, m-toluidine, P-
Toluidine, O-ethylaniline, m-ethylaniline, p-ethylaniline, O-isoprotoluaniline, m
-isopro and luaniline, p-isopropylaniline,
0-n-propylaniline, 0-Lert-butylaniline, p-terL-butylaniline, on-butylaniline, p-5ee-butylaniline, 2.3-xylidine, 2.4-xylidine, 2.6 -Xylidine, 3.4-xylidine, 3.5-xylidine, 2-methyl-3-ethylaniline, 2-methyl-4-isopropylaniline, 2.6-dichloroaniline, 2-ethyl-5-tert-butylaniline , 2,4-diisopropylaniline, 2,4,6-drimethylaniline, 4
-chloroaniline, 4-bromoaniline, 4-fluoroaniline, 3-chloroaniline, 3-bromoaniline,
3.4-dichloroaniline, 3-chloro-o-toluidine, 3-chloro-p-toluidine, 2.6-dimethyl-4-chloroaniline, O-aminophenol, m-aminophenol, p-aminophenol 2-amino -4
-cresol, 4-amino-2-Lert-butylphenol, 2,6-dimethyl-4-aminophenol, 2
．． 6-dichloro-4-aminophenol, 2-amino-1
, 3-resorcin, 4-amino-1,3-resorcin,
2-aminopytroquinone, 2-methoxyaniline, 3
-methoxyaniline, 4-methoxyaniline, 2-isopropoxyaniline, 2,4-dimethoxyaniline,
0-phenylenediamine, m-phenylenediamine, p
-phenylenediamine, 2,4-diaminotoluene,
2.6-diaminotoluene, 2.4-diaminoethylbenzene, 2.6-diaminoethylbenzene, 2.4
-Diaminoisopropylbenzene.

2.4-diamino-Lert-butylbenzene, 2,
6-diamino-terL-butylbenzene, 2,4-diamino-1,3-dimethylbenzene, 1. ! -dimethyl-4-aminoindan, 1,1-dimethyl-4,6
- Diamitindan, etc. can be mentioned. Preferred compounds are aniline, toluidines, xylidines, aminophenols and diamines, particularly preferred is aniline.

The reaction between the aralkyl alcohol derivative (IT) and the aromatic amine compound (III) is carried out in the presence of an acid catalyst such as hydrochloric acid, using 1 to 15 mol, preferably 1.1 mol, of the aromatic amine compound per 1 mol of the aralkyl alcohol derivative. Condensation reaction is carried out at a temperature of 170 to 240 °C for 10 to 40 hours in a proportion of ~10 moles. After the reaction is completed, the reaction mixture is neutralized using an alkali such as caustic soda, and after washing with water, the excess aromatic amine compound is removed. By removing under reduced pressure, the formula (I
It is possible to obtain the aromatic amine resin of I).

The molecular weight range of the aromatic amine resin obtained is Coro 0 to 60.
,000, and the resin is liquid at room temperature to a softening point of 250.
℃ (ring and ball softening point according to JIS K-2548).

A polyamino bismaleimide resin is obtained from the N,N'-4,4°-diphenylmethane bismaleimide represented by the above formula (I) and the aromatic amine resin represented by the formula (II). Various methods can be adopted.

(1) Bismaleimide and aromatic amine resin are pulverized and mixed in a solid-solid state, a solid-liquid mixture, or a prepolymer obtained by heat treatment is pulverized into pellets or powder. do. In this case, the heating conditions should be those that partially cure the prepolymer.
Generally, it is appropriate to heat the treatment at a temperature of 70 to 220°C for 5 to 240 minutes, preferably at a temperature of 80 to 200°C for 10 to 180 minutes.

(2) Bismaleimide and aromatic amine resin are dissolved in an organic solvent, then discharged into a poor solvent, and the precipitated crystals are filtered and dried to form a pellet or powder, or after being dissolved in an organic solvent, heat treatment is performed. After partially curing to the stage of prepolymer, it is discharged into a poor solvent and the precipitated crystals are carefully dried to form a pellet or powder. The conditions in this case also conform to (1).

The organic solvents that can be used are limited by the fact that they do not substantially react with both components, but it is also desirable that they are good solvents for both reaction components.Usually, the reaction solvents used are methylene chloride and dichloroethane. , halogenated hydrocarbons such as trichloroethylene, ketones such as acetone, methyl ethyl ketone, cyclohexanone, and diisopropyl ketone, ethers such as tetrahydrofuran, dioxane, and methyl cellosolve, aromatic compounds such as benzene, toluene, and chlorobenzene, acetonitrile, N, N- Examples include aprotic polar solvents such as dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, N-methyl-2-birosotone, and l,3-dimethyl-2-imidazolidinone.

The blending amount of aromatic amine resin represented by formula (n) is 1 formula (
The proportion is 5 to 100 parts by weight, preferably 10 to 80 parts by weight, based on 100 parts by weight of N,N'-1t,4'-diphenylmethane bismaleimide represented by 1).

If the amount of aromatic amine resin is less than 5 parts by weight, the cured product will be extremely brittle and will not have satisfactory bending strength, and if it exceeds 100 parts by weight, the heat resistance of the cured product will be poor.

A thermosetting resin composition is obtained from the polyamino bismaleimide resin and glass am described in L, and the glass fiber is made into a thin fiber with a predetermined diameter by rapidly cooling the molten glass while drawing it using various methods. It means a strand in which single fibers are bundled together with a binding agent, a roving in which the strands are evenly aligned and oriented toward the east, and any of these can be used in the present invention. The glass fiber is the base material 84 of the present invention.
In order to have affinity with pilgrims, silane coupling agents such as aminosilane and epoxysilane, chromic chloride, and other surface treatment agents depending on the purpose can be used.

The length of the glass fiber in the present invention greatly affects the physical properties of the molded product obtained and the workability during production of the molded product. Generally, the longer the length of the glass fiber, the better the physical properties of the molded article, or conversely, the worse the workability during production of the molded article. Therefore, in the present invention, the length of the glass fiber is [1,1 to 6
ms, preferably in the range of 0.3 to 4 .mu.ms, which is appropriate in order to balance both the physical properties and workability of the molded article.

The glass fiber in the present invention can be used in an amount of 10 to 400 parts by weight, preferably 20 to 300 parts by weight, based on 100 parts by weight of the polyamino bismaleimide resin. If it is less than 10 parts by weight, the reinforcing effect peculiar to glass fiber, which is a feature of the present invention, cannot be obtained.On the other hand, if it is used in excess of 400 parts by weight, the fluidity of the composition during molding will deteriorate, making it difficult to obtain a satisfactory molded product. difficult to obtain.

The thermosetting resin composition according to the present invention can be produced by a generally known method, but the following method is particularly preferred.

(1) Mix polyamino bismaleimide resin powder and glass powder using a mortar, Henschel mixer, drum blender, tumbler blender, ball mill, etc.
After kneading with a melt mixer and hot roll T as necessary,
Grind into pellets or powder.

(2) Polyamino bismaleimide resin powder is dissolved or suspended in an organic solvent in advance, glass fibers are immersed in this solution or suspension, the solvent is removed in a hot air oven, and then it is formed into pellets or powder. do. In this case, the temperature or time required for kneading varies depending on the properties of the polyamino bismaleimide resin used.The softening temperature of one composition is 70°C to 180°C, and the gelling time is 200°C.
Adjust as appropriate so that the time is within the range of 30 to 180 seconds.

A polymerization catalyst may be added to the thermosetting resin composition of the present invention if necessary, and the amount of the catalyst used is not particularly limited, or is 0.001 to 1%, based on the total weight of the polymer. Particularly preferred examples of the combined catalyst include benzoyl peroxide, t-phthyl hydroberoxide,
Known free radical catalysts such as dicumyl peroxide, azobisisobutyronitrile, and azobiscyclohexanecarbonitrile are effective. Note that the polymerization catalysts may be used in appropriate combinations.

In addition, the composition of the present invention may be supplemented with conventional additives such as antioxidants, heat stabilizers, ultraviolet absorbers, flame retardant aids, antistatic agents, lubricants, colorants, etc., to the extent that the objects of the present invention are not impaired. One or more types of additives may be added.

In addition, other thermosetting resins (e.g., phenolic resins, epoxy resins, etc.), thermoplastic resins (e.g., polyethylene, polypropylene, polyamide, polycarbonate,
(polysulfone, boethersulfone, polyetheretherketone, modified polyphenylene oxide, polyphenylene sulfide, fluororesin, etc.) or reinforcing materials such as carbon fiber, aromatic polyamide fiber, alumina fiber, potassium titanate fiber, clay, mica, silica, etc. , graphite, glass peas, alumina, calcium carbonate, and other fillers can also be blended in appropriate amounts depending on the purpose.

The thermosetting resin composition of the present invention can be produced by compression molding.

It is molded by a known molding method such as a transfer molding method, an extrusion molding method, an injection molding method, etc., and is put into practical use.

[Example] The present invention will be explained below with reference to examples.

Synthesis Example 1 In a reaction vessel equipped with a stirrer, a thermometer, and a Dean-Stark azeotropic distillation trap, 1116 g of aniline as an aromatic amine compound represented by the formula (I[I) (1
- 665 g (4,0 mol) of α,α-dimethoxy-P-xylene as an aralkyl alcohol derivative represented by the formula (mV) and 626 g (6,0 mol) of a 35% aqueous hydrochloric acid solution as a catalyst. 0 mol) was charged, and the temperature was raised while blowing nitrogen gas. Water distilled into the trap was removed from the system when the internal temperature reached about 110°C. When the temperature was further increased to about 130°C, distillation of methanol was observed, and the temperature continued to increase while distilling off the methanol produced.
After reaching 170°C, the temperature was maintained for 3 hours. After almost no methanol was generated, the temperature was continued to rise and the reaction was carried out at 190 to 200°C for 12 hours.

Next, the mixture was cooled to lower the internal temperature to 95° C., and 1,680 g of a 15% Y-base soda aqueous solution was added thereto for neutralization with stirring. After standing still, the lower aqueous layer was separated and removed, and 300% saturated saline solution was added.
Next, the solution was separated by adding 0 g of the solution and washing, followed by heating and dehydration under a nitrogen stream, followed by pressure-filtering to remove inorganic salts and the like. This was concentrated in vacuo under a vacuum of 2 to 35 ml to recover 519 g of unreacted aniline. The remaining amount was discharged to obtain 945 g of light brown aniline resin.

As a result of compositional analysis of the aromatic amine resin obtained as described above by high performance liquid chromatography, it was found that - formula (I
I) n=0 is 28, n=1 is! 6.8. n=2
is 10.5, and n=3? , 8, n≧4 is 16.9
(mol%).

In addition, the amine per 1 (perchloric acid-glacial acetic acid method) of this resin is 0.578 equivalent/(100 g), and it is -25 in JIS.
The softening point measured using a ring and ball softening point measuring device according to 48 is 6.
The temperature was 8°C, and the average molecular weight was 960.

Synthesis Example 2 Using 745 g (8.0 mol) of aniline, 664 g (4.0 mol) of α,α'-dimethoxy-P-xylene, and 420 g (4.0 mol) of a 35% aqueous hydrochloric acid solution as a catalyst, the following reaction was performed. The reaction was carried out in the same manner as in Synthesis Example 1.

747 g of light yellowish brown aniline resin was obtained.

As a result of compositional analysis of the aromatic amine resin obtained in the above manner by high performance liquid chromatography, - formula (■
), n=o is 17.0. n = l is 14.5, n = 2
is 112. n≧3 was 55.2 (mol%).

In addition, the amine equivalent of this resin is 0.520 equivalent/'(1
00g), the softening point was 61°C, and the average molecular weight was 2100.

Synthesis Example 3 As an aromatic amine compound represented by general formula (m), 2.
13
2 g of reddish brown oily diaminotoluene resin was obtained.

As a result of compositional analysis of the aromatic amine resin obtained as described above by high performance liquid chromatography, it was found that - formula (n
), n=o is 44.5. n = 1 is 29.7, n =
2 was 14.6, and n≧3 was 11.2 (mol%).

Moreover, the amine equivalent of this resin is 1.204.

The softening point was 46°C and the average molecular weight was 550.

Synthesis Example 4 Using 121.1 g (1.3 mol) of aniline as an aromatic amine compound represented by general formula (m), - formula (
α as an aralkyl alcohol derivative represented by rV)
, α-dihydroxy-m-xylene 1311.2 g
(1.0 mol) and 33 g of concentrated sulfuric acid (
The reaction was carried out in the same manner as in Synthesis Example 1 except that 0.125 mol) was used, and 151 g of a pale M brown aniline resin was obtained.

The amine equivalent of the aromatic amine resin obtained as described above was 0.496, the softening point measured using a ring and ball softening point measuring device according to JIS -2548 was 118°C, and the average molecular weight was 6500. .

Synthesis Example 5 In a reaction vessel, 109 g (1.0 mol) of p-aminophenol as an aromatic amine compound represented by the general formula (01) and α as an aralkyl alcohol derivative represented by the general formula (1'V) were added. , 110.2 g (0.5 mol) of α°-diacetoxy-P-xylene, 6.8 g (0.05 mol) of zinc chloride as catalyst and 19 g (0.1 mol) of pt-luenesulfonic acid. The reaction was carried out under reduced pressure using a water jet pump.The reaction started at about 130°C and was raised to 170°C in 3 hours.

During the process, acetic acid produced was collected in a cryogenic trap.

After maintaining the same temperature for 3 hours, the reaction temperature was further increased to 200℃.
The mixture was aged for 1 hour at 200 to 210°C, and then completed. After cooling to 95°C, 300% of toluene was added, stirred and dissolved, and 20% of triethylamine was added thereto.
After adding 2 g of water, 2,001 g of water was added and stirred, and the mixture was left still to separate and remove the lower aqueous layer. One more time, water 2
After washing with water and separating the mixture with water, toluene and unreacted p-aminophenol were removed by vacuum evaporation. 138 g of a co-condensed resin of p-aminophenol was obtained as the resulting brown resin residue.

The amine equivalent of the aromatic amine resin obtained as described above was 0.525, the softening point measured with a ring and ball softening point measuring device according to JIS -2548 was 94°C, and the average molecular weight was 2200. .

Synthesis Examples 6 to 14 Table 1 shows the type of aromatic amine compound represented by the general formula (m), the type and name of the aralkyl alcohol derivative represented by the general formula (rlr), the type and @ of the catalyst, and the reaction conditions. The reaction was carried out in the same manner as in Synthesis Example 1 except as shown in Table 1.
Various aromatic amine resins as shown in 1 were obtained.

Examples 1 to 5 N,N'-4,4°-diphenylmethane bismaleimide and the aromatic amine resin 1 resin obtained in Synthesis Example 1 were placed in a stainless steel reaction vessel equipped with a stirrer, a reflux condenser, and a nitrogen introduction tube. Charge each part by weight shown in Table 2 and heat to 180°C.
Melt by heating for 20 minutes at 150°C and under reduced pressure (10~
After defoaming for 30 minutes (15 s + mHg), the reaction product was cooled to room temperature and solidified into a brown, transparent glass. A fine yellow powder of bismaleimide resin was obtained. The softening temperature was 98°C and the gel time was 653' at 200°C.

Silane-treated glass fiber M (manufactured by Nittobo Co., Ltd., C5-3P) with a fiber diameter of 137 zm and a fiber #l length of 3 s was added to 100 parts by weight of the obtained polyamino bismaleimide resin powder.
E-476S) was added in the amount shown in Table 2.

The mixture was mixed using a small drum blender A (manufactured by Yoda Seisakusho) to obtain a thermosetting resin composition.

The composition was heated to 180°C in a mold (lux 80X4
t) while heating and melting, the pressure is 50 kg/
cm", and compression molded by holding at 200°C for 30 minutes.

Thereafter, the molded product was cooled to room temperature, taken out from the mold, and post-cured for 4 hours in a hot air gear oven at 250° C. to obtain an Izot MiNX test piece and a bending test piece. Izotsu impact test (Notsuchi Ushi) 1 bending test and measurement of heat distortion temperature (18.5 kg/cm2) are in accordance with JIS
The test was carried out according to K-6911, and the results shown in Table 2 were obtained.

Example 6 1501 parts by weight of acetone was added to 100 parts by weight of the polyamino bismaleimide resin obtained in the same manner as in Example 2 to form a suspension solution, and to this was added silane having a fiber diameter of 13 m and a fiber length of 3 cm. Treated glass fiber (manufactured by Nittobo Co., Ltd.)
C3-IPE-476S) was added and uniformly dispersed. Further, this was pre-dried in a hot air oven at 60° C. for 20 hours, and then dried under reduced pressure in a vacuum dryer at 50° C. for 5 hours to completely remove the solvent acetone, thereby obtaining a glass fiber-impregnated powder. Hereinafter, the same operations as in Examples 1 to 5 were carried out to obtain test pieces for measuring physical properties. The obtained test pieces were measured in the same manner as in Examples 1 to 5, and the results shown in Table 2 were obtained.

Examples 7-19. Comparative Examples 1 to 3 Examples 1 to 3 were prepared based on 100 parts by weight of polyamino bismaleimide resin obtained from 66.7 parts by weight of the bismaleimide compound shown in Table 2 and 33.3 parts by weight of aromatic amine resin.
Glass fiber used in step 5 (manufactured by Itsubunsei Co., Ltd., C3-:l
PE-4763) was added in the amount shown in Table 2. below,
The same operations as in Examples 1 to 5 were carried out to obtain the results shown in Table 2.

[Effects of the invention] The thermosetting resin of the invention has excellent heat resistance, impact resistance and -
UT has flexibility and is expected to be widely used in electrical and electronic parts, various structural members, W1 moving parts, etc., and its use in industry E is great.

Ki4shi license applicant

Claims (1)

[Claims] Formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ N,N'-4,4'-diphenylmethane bismaleimide represented by (I) and aromatic represented by formula (II) Group amine resins ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (II) (In the formula, A represents a phenylene group, an alkyl-substituted phenylene group, a diphenylene group, a diphenyl ether group, or a naphthylenyl group, and R^1 represents a halogen atom, a hydroxyl group, Represents a lower alkoxy group having 4 or less carbon atoms or a lower alkyl group having 5 or less carbon atoms, and R^1 may be the same or different from each other, and may form a ring. l is 1 or 2
, m represents an integer of 0 to 3, and n represents an integer of 0 to 300. ) A thermosetting resin composition comprising 100 parts by weight of a polyamino bismaleimide resin and 10 to 400 parts by weight of glass fiber.