JP2001234029A - Thermosetting resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a thermosetting resin composition shortened in curing time and capable of maintaining the properties of the cured product thereof such as mechanical strength. SOLUTION: This thermosetting resin composition essentially comprises (A) a novolak-type phenolic resin, (B) a compound having 3,4-dihydro-2H-1,3- benzoxazine structure and (C) hexamethylenetetramine; wherein the components A and B account for 80-99.5 wt.% and 0.5-20 wt.% of the total of the components A and B, respectively, the number of 3,4-dihydro-2H-1,3-benzoxazine rings contained in a total of 100 g of the components A and B is 0.005-0.09, and the compounding amount of the component C is 7-25 pts.wt. based on a total of 100 pts.wt. of the components A and B.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a thermosetting resin composition which is extremely excellent in quick-curing property and is useful for molding materials.

[0002]

2. Description of the Related Art Phenolic resin molding materials are widely used in automobile parts, electronic and electric parts, kitchen parts, etc. because of their excellent heat resistance, durability, electric and mechanical performance. The molding time for molding these molding materials has a significant effect on production costs. In other words, if the curing time can be shortened compared to conventional products, a high cycle of the molding process is achieved, and by improving workability,
Further, the productivity can be increased.

[0003] In order to shorten the curing time of a phenol novolak resin molding material, various improvements of a resin composition comprising a phenol novolak resin and hexamethylenetetramine have been made. For example, phthalic acid, benzoic acid, and various carboxylic acids such as salicylic acid, p-toluenesulfonic acid, and a method of mixing acidic substances such as various sulfonic acids such as benzenesulfonic acid in the resin composition, the above-mentioned acidic substance and basic Examples include a method of mixing a complex salt of a substance with a resin composition, and a method of using a high ortho novolak in place of a normal random novolak, or a method of using a combination thereof. By using these methods, the curing time can be shortened to some extent, but the strength of the cured product is reduced, and the gas generated from the acidic substance is released at the time of heating, thereby contaminating the mold and working. There are disadvantages such as affecting the environment.

On the other hand, 3,4-dihydro-2H-1,3-
Compounds having a benzoxazine structure are known to bind to phenolic compounds by a ring-opening reaction (J. Am. Chem. Soc., 3423 (1965)), unlike additives intended to shorten the curing time. It is known that no gas is released during heat curing.

Japanese Patent Application Laid-Open No. Hei 9-272786 discloses a thermosetting resin composition comprising a thermosetting resin having a dihydrobenzoxazine ring and a novolak-type phenol resin, in which a small amount of hexamethylenetetramine is added. This shows that the composition cures quickly, but its cure properties were not satisfactory.

[0006]

DISCLOSURE OF THE INVENTION The present invention has been intensively studied in order to solve the drawbacks of the conventional rapid curing technology, and shortens the curing time during molding without deteriorating the properties of the cured product such as strength. It is an object of the present invention to provide a thermosetting resin composition that can be used.

[0007]

Means for Solving the Problems The present inventors have developed a novolak type phenol resin and 3,4-dihydro-2H-
By using a compound having a 1,3-benzoxazine structure and hexamethylenetetramine as essential components,
The present inventors have found a thermosetting resin composition capable of shortening the curing time without impairing the physical properties of the cured product such as strength, and have completed the present invention.

That is, the present invention relates to (1) a novolak-type phenol resin (A), a compound (B) having a 3,4-dihydro-2H-1,3-benzoxazine structure in a molecule, and a hexamethylenetetramine (C) ) As an essential component, and the ratio of the component (A) to the total amount of the component (A) and the component (B) is 80% by weight.
Not less than 99.5% by weight, the proportion of component (B) is not less than 0.5% by weight and not more than 20% by weight, and the amount of 3,4-containing in the total amount of 100 g of component (A) and component (B) 0.005 of dihydro-2H-1,3-benzoxazine rings
The component (C) is added in an amount of not less than 0.09 and not more than 0.09, and the total amount of the component (A) and the component (B) is 10
A thermosetting resin composition characterized by being mixed in an amount of 7 parts by weight or more and 25 parts by weight or less with respect to 0 parts by weight,

(2) A random novolak in which a novolak type phenol resin (A) is synthesized at a molar ratio (F / P ratio) of formaldehyde (F) to phenol (P) of 0.4 to 0.95. The thermosetting resin composition according to (1), which is a high-ortho novolak or a mixture thereof, and wherein the amount of free phenol in the novolak-type phenol resin is 10% by weight or less.

(3) 3,4-dihydro-2H in the molecule
Compound (B) having -1,3-benzoxazine structure
Is a compound (D) having two or more hydroxyphenylene groups in which hydrogen is bonded to at least one of the ortho positions of the phenolic hydroxyl group in the molecule, a primary amine and formaldehyde, (1) synthesized by reacting a primary amine at a ratio of 0.5 mol or more and 1.0 mol or less and a formaldehyde at a ratio of 2 mol per 1 mol of the primary amine with respect to 1 mol of the phenolic hydroxyl group. The thermosetting resin composition according to item or (2),

(4) The primary amine is an aromatic amine represented by the formula (1), (1), (2) or (3)
Item thermosetting resin composition,

Embedded image (In the formula, R _{1 to} R ₅ represent hydrogen or an alkyl group having 10 or less carbon atoms.)

(5) The primary amine is an aliphatic amine having 10 or less carbon atoms, (1), (2) or (3).
Item thermosetting resin composition,

(6) The primary amine is an alicyclic amine having 10 or less carbon atoms, (1), (2) or (3).
Item thermosetting resin composition,

(7) The compound (D) is bisphenol A, (1), (2), (3), (4),
(5) or the thermosetting resin composition according to (6),

(8) The compound (D) is bisphenol F alone or a mixture of bisphenol F regioisomers (1), (2), (3), (4) and (5)
Item, or the thermosetting resin composition according to (6),

(9) The compound (D) has a number average molecular weight of 8
(1), (2), (3), (4), (5)
Or the thermosetting resin composition as described in (6).

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The novolak type phenol resin (component (A)) used in the present invention is obtained by reacting phenol and formaldehyde in an acidic to neutral range. The novolak-type phenol resin may be modified for the purpose of imparting curability, heat resistance, or flexibility.

[0018] Such modifiers include cresol,
Alkylphenols such as xylenol, butylphenol and nonylphenol, polyhydric phenols such as catechol, resorcinol, and hydroquinone; polynuclear phenols such as bisphenol A, bisphenol F and bisphenol; aromatic hydrocarbons such as toluene, xylene and mesitylene; tung oil And drying oils such as linseed oil, dicyclopentadiene, etc., and one or more of these may be used in combination.

Further, in the component (A), the charged molar ratio (F / F) of formaldehyde (F) to be reacted with a phenol (P) containing a phenol compound mentioned as a modifier.
P) is preferably from 0.4 to 0.95, more preferably from 0.65 to 0.9, and may be any of random novolak, high ortho novolak, or a mixture thereof. It is desirably 10% by weight or less.

The compound having a 3,4-dihydro-2H-1,3-benzoxazine structure (component (B)) in the molecule used in the present invention is 3,4-dihydro-2H-1,3-
It is not particularly limited as long as it is a compound having a benzoxazine structure, and more preferably, a compound having two or more hydroxyphenylene groups in which hydrogen is bonded to at least one of the ortho positions of the phenolic hydroxyl group in the molecule. , A primary amine and formaldehyde with respect to 1 mol of the phenolic hydroxyl group of the compound, and
It is synthesized by reacting using not less than 1.0 mole and not more than 1.0 mole, and 2 moles of formaldehyde per mole of primary amine.

The component (B) used in the present invention comprises a compound having a phenolic hydroxyl group, a primary amine and formaldehyde in the above-mentioned equivalence ratio, in a solvent or without a solvent.
It is obtained in a high yield by reacting at 0 ° C. or more and 130 ° C. or less, but in order to obtain a target compound with high purity, the equivalent ratio of each raw material compound is adjusted within a range of 0.5 equivalent or less. It is perfectly acceptable to wash the crude product after the reaction with a basic, neutral or acidic solution, or to purify it by general means such as distillation or recrystallization.

Examples of the compound having a phenolic hydroxyl group used for synthesizing the component (B) include phenol, alkylphenols such as cresol, xylenol, ethylphenol, butylphenol and nonylphenol, methoxyphenol and ethoxyphenol. And the like, bisphenol A, bisphenol F and its positional isomers, dihydric phenols such as bisphenol S, and phenol formaldehyde resins. Preferred are bisphenol A, bisphenol F and its positional isomers. Phenol formaldehyde resins having an average molecular weight of 800 or less are exemplified.

Examples of the formaldehyde source include paraform, an aqueous formalin solution, and trioxane.

Examples of the primary amine compound include aliphatic amines having 10 or less carbon atoms such as methylamine, ethylamine, butylamine and hexylamine, alicyclic amines having 10 or less carbon atoms such as cyclohexylamine, aniline and toluidine. Aromatic amines represented by the formula (1) are preferably used. Particularly preferably, methylamine, cyclohexylamine or aniline is used.

The compounding ratio of the component (B) in the resin composition of the present invention is such that the ratio of the component (A) to the total amount of the components (A) and (B) is 80% by weight or more and 99.5% by weight or less. And the proportion of the component (B) is 0.5% by weight or more and 20% by weight or less, and the total amount of the component (A) and the component (B) is 100%.
The number of 3,4-dihydro-2H-1,3-benzoxazine rings contained in g is 0.005 or more and 0.09 or less. In particular, in the resin composition of the present invention, even if the compounding amount of the component (B) with respect to the total amount of the component (A) and the component (B) is from 0.5% by weight to less than 5% by weight, the present invention The feature is that a sufficient effect can be obtained to achieve the purpose. If less than this, the effect of shortening the curing time is not sufficiently exhibited, and if it is more than this, the curing action is too much, and during the production of the resin composition, a problem such as partial gelation of the composition occurs, and as a result, This is undesirable because it leads to a decrease in the strength of the cured product. Component (B) may be used alone or in combination of two or more depending on the application.

The hexamethylenetetramine (component (C)) used in the present invention is usually used in the form of a powder, and based on 100 parts by weight of the total amount of the components (A) and (B).
7 to 25 parts by weight are blended. The amount of the component (C) is
If the amount is less than this, the number of cross-linking points decreases, which may cause a problem such as a decrease in the strength of the cured product. If it is more than this, the amount of gas generated by decomposition of the component (C) increases,
In addition, an excessive amount of the component (C) that cannot be reacted remains in the cured product of the resin composition, causing problems such as deterioration of cured product characteristics, which is not desirable.

In the thermosetting resin composition of the present invention, an organic filler, an inorganic filler, a release agent, a colorant, and the like can be added as a filler if necessary. As organic or inorganic fillers, wood powder, pulp powder, various crushed fabrics, organic powders such as thermosetting resin cured products and crushed molded products, silica, alumina, aluminum hydroxide, glass, talc, clay, Examples include inorganic powders such as mica, calcium carbonate, and carbon, and inorganic fibers such as glass fiber and carbon fiber. One or more of these fillers can be used.

The thermosetting resin composition of the present invention can be produced by mixing the above components by a general method and kneading the mixture by a known technique such as a hot roll or a kneader.

The thermosetting resin composition of the present invention has heat resistance,
It can be used for molding materials such as automobile parts, electronic / electric parts, and kitchen parts that require durability, electric and mechanical performance.

[0030]

The following examples are provided to illustrate the present invention, but do not limit the present invention.

First, an example of the synthesis of the component (B) used in the examples will be described. (Synthesis Example 1) 27 g (0.8 mol) of 88% paraform and 43 g of o-toluidine were placed in a 300 ml separable flask equipped with a stirring blade, a Dimroth condenser, and a thermometer.
(0.4 mol), 46 g of bisphenol A (0.2 m
ol) and 50 ml of 1,4-dioxane, and gradually heated to 80 ° C. while stirring, and reacted at 80 ° C. for 5 hours. To the solution after the reaction, add toluene 1000
Then, the mixture was washed twice with 1000 ml of ion-exchanged water using a separating funnel. After removing water with anhydrous sodium sulfate, the compound (a) was obtained by distilling off toluene under reduced pressure. ^By analysis using ¹ H-NMR, it was confirmed that 3,4-dihydro-2H-1,
The number of 3-benzoxazine rings was 3.9 × 10 ⁻³ .

(Synthesis Example 2) In a 300 ml separable flask equipped with a stirring blade, a Dimroth condenser, and a thermometer, 40 g (0.2 mol) of bisphenol F, 37 g (0.4 mol) of aniline, and a 37% aqueous solution of formalin 6
5 g (0.8 mol) and 50 ml of toluene were charged, and the temperature was gradually raised while stirring, and the reaction was carried out at 80 ° C. for 4 hours. Then, the water and toluene in the reaction system were heated at 100 ° C.
The compound (b) was obtained by removing under reduced pressure so as not to exceed. Analysis using ¹ H-NMR revealed that 3,4-dihydro-2H-1,3-
The number of benzoxazine rings was 3.8 × 10 ⁻³ .

(Synthesis Example 3) In a 300 ml separable flask equipped with a stirring blade, a Dimroth condenser, and a thermometer, 62 g (0.76 g) of a 37% aqueous solution of formalin, p
-41 g (0.38 mol) of toluidine, novolak type phenol resin (number average molecular weight 600, OH equivalent 10
4) 50 g and 100 ml of 1,4-dioxane were charged,
Stir at room temperature until a homogeneous solution is obtained. Thereafter, the temperature of the mixture was gradually raised to 90 ° C. while stirring, and the mixture was reacted at 90 ° C. for 6 hours. To the obtained reaction mixture, 1000 ml of toluene was added, and the mixture was washed twice with 1000 ml of ion-exchanged water using a separating funnel. After removing water with anhydrous sodium sulfate, toluene was distilled off under reduced pressure to obtain a compound (c). ¹ H-N
Analysis using MR revealed that 3 g contained in 1 g of this compound
The 4-dihydro-2H-1,3-benzoxazine ring is
It was 3.5 × 10 ^-3 pieces.

Synthesis Example 4 A 300 ml separable flask equipped with a stirring blade, a Dimroth condenser, and a thermometer was charged with 3
65 g (0.8 mol) of a 7% formalin aqueous solution, 46 g (0.2 mol) of bisphenol A, and dioxane 1
Then, the mixture was stirred at room temperature until a homogeneous solution was obtained. To this solution was added 40 g of cyclohexylamine (0.
4 mol) was added slowly, and the mixture was further stirred at room temperature for 1 hour. Thereafter, the temperature was gradually raised to 80 ° C., and the reaction was performed for 4 hours. To the obtained reaction solution, 1000 ml of cyclohexane was added, washed twice with 1000 ml of ion-exchanged water, and dried over anhydrous sodium sulfate. Compound (d) was obtained by removing cyclohexane under reduced pressure. ¹ H-NMR
Analysis showed that 3,4-compounds contained in 1 g of this compound
The dihydro-2H-1,3-benzoxazine ring has a structure of 3.
9 × 10 ⁻³ pieces.

(Synthesis Example 5) 65 g (0.8 mol) of a 37% aqueous solution of formalin was placed in a 300 ml separable flask equipped with a stirring blade, a Dimroth condenser, and a thermometer.
50 ml of 1,4-dioxane are charged and stirred at room temperature.
Here, 31 g of a 40% aqueous methylamine solution (0.4 mol
l) Subsequently, a solution of 38 g (0.4 mol) of phenol and 50 ml of 1,4-dioxane was slowly added dropwise, and the mixture was stirred at room temperature until it was sufficiently reacted. This mixed solution is heated and reacted at 60 ° C. for 6 hours. To the solution after the reaction, 1000 ml of n-hexane was added, and the mixture was washed twice with 1000 ml of ion-exchanged water using a separatory funnel. After removing water with anhydrous sodium sulfate, n-hexane was added under reduced pressure.
The hexane was distilled off to obtain a compound (e).
^According to analysis using ¹ H-NMR, the number of 3,4-dihydro-2H-1,3-benzoxazine rings contained in 1 g of the compound was 7.1 × 10 ⁻³ .

Next, after blending the components (A), (B) and (C) to obtain a resin composition, the characteristics were evaluated. In order to measure various characteristics in Examples, The measurement method used is described below. 1. Gel time measurement A sample of 1 g was placed on a hot plate kept at 150 ° C, and the time until the resin composition did not pull the yarn even when the spatula was lifted while constantly stirring with a spatula was measured. The shorter the time, the faster the curing. 2. Measurement of Curing Degree by Curast Meter Curast Meter (Orientec Co., Ltd., JSR Curast Meter SD
Mold), the thermosetting resin composition obtained in the example was 5.0
g, the curing speed and the maximum torque were measured. The curing speed is a gradient from 10% to 90% of the maximum torque and is derived from the following equation, and the unit is N · m / s. Curing speed (Nm / s) = (maximum torque (Nm) x
0.9−maximum torque (N · m) × 0.1) ÷ (time at which torque value reaches 90% of maximum torque (s) −time at which torque value reaches 10% of maximum torque (s)) The maximum torque is a parameter indicating the elasticity at the measurement temperature. The larger the value, the higher the elasticity at the time of heating. 3. Measurement of flexural strength and flexural strength during heating The resin composition was measured for 170
A bending test piece was prepared by molding at ℃ 5 minutes, and JIS K6911
, The flexural strength at room temperature and the flexural strength at 120 ° C were measured.

(Example 1) As the component (A), F / P =
0.82, 5 g of free phenol, 49 g of novolak type phenol resin having an ortho-para ratio of 0.75 (hereinafter referred to as novolak X), and F / P = 0.75, 6 wt% of free phenol, and ortho-para ratio of 2 Novolak-type phenol resin (hereinafter referred to as novolak Y)
49 g, 2 g of the compound (a) obtained in Synthesis Example 1 as the component (B), and 20 g of hexamethylenetetramine as the component (C) were dry-blended with a mixer to obtain a composition. The gel time of this composition at 150 ° C. was 43 seconds. In addition, the same weight of calcium carbonate is dry-blended with a mixer to this composition,
Use this to measure the curast meter,
The flexural strength at 20 ° C. was measured. The resulting curastometer curing rate is 7.40 × 10 ² N · m / s, the maximum torque is 7.65 × 10 ⁴ N · m, the flexural strength at room temperature is 77 MPa, and the flexural strength at 120 ° C. Is 34
MPa. The formulations and results are summarized in Table 1.

(Example 2) 49 g of novolak X used in Example 1 was added to 72 g, 49 g of novolak Y was added to 24 g, and 2 g of compound (a) was added to 4 g of compound (b) obtained in Synthesis Example 2. 1 g of 20 g of hexamethylenetetramine
A composition was obtained and evaluated in the same manner as in Example 1 except that the composition was changed to 5 g. The formulations and results are shown in Table 1.

Example 3 Novolak X49 g and Novolak Y49 g used in Example 1 were converted to Novolak X85 g.
A composition was obtained and evaluated in the same manner as in Example 1 except that 2 g of the compound (a) was replaced with 15 g of the compound (c) obtained in Synthesis Example 3, and 20 g of hexamethylenetetramine was replaced with 10 g. went. The formulations and results are shown in Table 1.

Example 4 Novolak X49g and Novolak Y49g used in Example 1 were replaced with Novolak X92.
20 g of hexamethylenetetramine was added to 7.5 g of the compound (d) obtained in Synthesis Example 4 and 2 g of the compound (a) to 5 g.
Was changed to 15 g, and a composition was obtained and evaluated in the same manner as in Example 1. The formulations and results are shown in Table 1.

Example 5 Novolak X49 g and Novolak Y49 g used in Example 1 were converted to Novolak X88 g.
A composition was obtained and evaluated in the same manner as in Example 1, except that 2 g of the compound (a) was replaced with 10 g of 12 g of the compound (e) obtained in Synthesis Example 5 and 20 g of hexamethylenetetramine. went. The formulations and results are shown in Table 1.

Comparative Example 1 Only 100 g of Novolak X and 15 g of hexamethylenetetramine were blended, and a composition was obtained and evaluated in the same manner as in Example 1 below. The formulations and results are shown in Table 1.

Comparative Example 2 75 g of novolak X, 25 g of novolak Y, and 15 g of hexamethylenetetramine
g was blended, and a composition was obtained and evaluated in the same manner as in Example 1 below. The formulations and results are shown in Table 1.

(Comparative Example 3) Volak X used in Example 1
Novolak X 80 g
Then, a composition was obtained and evaluated in the same manner as in Example 1 except that 2 g of the compound (a) was changed to 20 g and 20 g of hexamethylenetetramine was changed to 5 g. The formulations and results are shown in Table 1.

Comparative Example 4 Volak X used in Example 1
Novolak X 75 g with Novolak Y 49 g
Then, a composition was obtained and evaluated in the same manner as in Example 1, except that 2 g of the compound (a) was changed to 25 g of the compound (b) and 20 g of hexamethylenetetramine was changed to 8 g. The formulations and results are shown in Table 1.

Comparative Example 5 A composition was obtained and evaluated in the same manner as in Example 1 except that the compound (a) used in Example 1 was changed to paratoluenesulfonic acid. The formulations and results are shown in Table 1.

(Comparative Example 6) Novolak X49g and Novolak Y49g used in Example 1 were replaced with Novolak X92.
A composition was obtained and evaluated in the same manner as in Example 1 except that 5 g, 2 g of the compound (a) was changed to 7.5 g of salicylic acid, and 20 g of hexamethylenetetramine was changed to 15 g. The formulations and results are shown in Table 1.

[0048]

[Table 1]

Comparing the examples with the comparative examples 1 and 2, which are conventional examples, the resin composition of the present invention can greatly reduce the curing time, and has a flexural strength at room temperature and 120 ° C. of a molded product. The maximum torque in the curast meter is almost the same. In Comparative Examples 4 to 6, the gel time and the curing speed of the curast meter are the same as those in the examples, but it can be seen that the maximum torque of the curast meter and the bending strength at normal temperature and 120 ° C. are reduced.

[0050]

According to the present invention, it is possible to obtain a thermosetting resin composition capable of shortening the curing time during molding without deteriorating the properties of the cured product such as strength. It is suitable for applications such as materials.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) // (C08L 61/06 (C08L 61/06 61:34) 61:34) F-term (Reference) 4J002 CC031 CC282 EN046 EU186 EU237 GN00 GQ00 4J033 CA02 CA11 CA12 CA13 CA18 CA19 CA31 CA37 CA42 CB03 FA01 FA02 FA04 FA11 HA07 HA12 HA28 HB01

Claims (9)

[Claims] 1. A novolak-type phenol resin (A), a compound (B) having a 3,4-dihydro-2H-1,3-benzoxazine structure in a molecule, and hexamethylenetetramine (C) as essential components, and The ratio of the component (A) to the total amount of the components (A) and (B) is 80% by weight or more and 99.5% by weight or less, and the ratio of the component (B) is 0.
The number of 3,4-dihydro-2H-1,3-benzoxazine rings is 5% by weight or more and 20% by weight or less and contained in 100 g of the total amount of the component (A) and the component (B).
It is blended in a range of at least 05 and at most 0.09, and the blending amount of component (C) is 10 (total amount of component (A) and component (B)).
A thermosetting resin composition, which is blended in an amount of 7 to 25 parts by weight based on 0 part by weight. 2. A novolak type phenol resin (A) comprising:
A random novolak, a high ortho novolak, or a mixture thereof, which is synthesized at a molar ratio (F / P ratio) of formaldehydes (F) and phenol (P) of 0.4 to 0.95; The thermosetting resin composition according to claim 1, wherein the amount of free phenol in the phenol resin is 10% by weight or less. 3. The method according to claim 1, wherein 3,4-dihydro-2H-1,
A compound (B) having a 3-benzoxazine structure, a compound (D) having two or more hydroxyphenylene groups in which hydrogen is bonded to at least one of the ortho positions of the phenolic hydroxyl group in a molecule, and a primary amine And formaldehyde with 0.5 mol or more and 1.0 mol or less of primary amine and 1 mol of formaldehyde with respect to 1 mol of phenolic hydroxyl group of compound (D).
The thermosetting resin composition according to claim 1, wherein the composition is synthesized by reacting at a molar ratio. 4. The thermosetting resin composition according to claim 1, wherein the primary amine is an aromatic amine represented by the formula (1). Embedded image (In the formula, R _{1 to} R ₅ represent hydrogen or an alkyl group having 10 or less carbon atoms.) 5. The thermosetting resin composition according to claim 1, wherein the primary amine is an aliphatic amine having 10 or less carbon atoms. 6. The thermosetting resin composition according to claim 1, wherein the primary amine is an alicyclic amine having 10 or less carbon atoms. 7. The compound according to claim 1, wherein the compound (D) is bisphenol A.
Or the thermosetting resin composition according to claim 6. 8. The compound (D) is bisphenol F alone,
7. The thermosetting resin composition according to claim 1, wherein the thermosetting resin composition is a mixture of bisphenol F positional isomers. 9. The compound according to claim 1, wherein the compound (D) is a phenol formaldehyde resin having a number average molecular weight of 800 or less.
The thermosetting resin composition according to the above.