JPH03281630A - Thermosetting resin composition and its use - Google Patents

Abstract

PURPOSE:To obtain a thermosetting resin composition desirable as a heat- resistant electrical insulation material of a low dielectric constant by mixing a fluorocyanamide compound with a fluoromaleimide compound. CONSTITUTION:A thermosetting resin composition is obtained by mixing a cyanamide compound of formula I (wherein Rf is a bifunctional group having at least one aromatic ring and at least one fluoropropylene group) {e.g. 2,2- bis[4-(4-cyanamidophenoxyl)phenyl]-1,1,1,3,3,3-hexafluoropropane} with a maleimide compound of formula II (wherein Rf is as defined above) {e.g. 2,2- bis[4-(4-maleimidophenoxyl)phenyl]-1,1,1,3,3,3-hexafluoropropane}. This composition contains fluorine atoms, therefore can effectively give a cured product of a low dielectric constant and is excellent in heat resistance and high- temperature mechanical properties, so that it is suitable as a molding material or an insulation material for electrical machines.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a thermosetting resin composition containing a fluorine-containing cyanamide compound and a fluorine-containing maleimide compound, and particularly relates to a thermosetting resin composition containing a fluorine-containing cyanamide compound and a fluorine-containing maleimide compound. ! The present invention relates to a thermosetting resin composition suitable as an edge material and its uses.

[Prior Art] Fluorine resins such as polytetrafluoroethylene (PTFE) or hydrocarbon resins such as polybutadiene are known as low dielectric constant insulating materials and are widely used. These have a relative dielectric constant of 3 or less, but since the former is a thermoplastic resin, it has a softening point, and therefore, when the temperature exceeds the softening temperature, the mechanical strength rapidly decreases.
The coefficient of thermal expansion increases. Furthermore, there is a problem that molding must be carried out by heating and melting since there is no suitable solvent.

On the other hand, thermosetting resins such as butadiene resin and allyl resin are known as the latter, and these have a three-dimensional crosslinked structure and are excellent as heat-resistant materials that require mechanical strength and dimensional stability at high temperatures. However, as can be inferred from its chemical structure, hydrocarbon resins are easily oxidized and have poor thermal decomposition characteristics.

In fields where such heat resistance is required, many resins having heteroaromatic rings such as imide rings are used. Typical resins with imide aromatic rings include polyimide, polybenzimidazole, polybenzothiazole,
Examples include bismaleimide-triazine, bismaleimide-diamine, bismaleimide-dicyanamide, cyanamide-maleimide, and the like.

Among these, bismaleimide-triazine, bismaleimide-diamine, and cyanamide-maleimide resins are known in the fields of prepregs, laminated materials, etc. as addition-type heat-resistant materials that do not produce side reaction products such as condensed water during curing reactions. . In particular, cyanamide-maleimide forms heteroaromatic rings such as melamine rings, isomelamine rings, and imide rings through a trimerization reaction when heated without using a catalyst, resulting in a material with excellent heat resistance (Japanese Patent Application Laid-open No. 79017/1983). .

[Problems to be Solved by the Invention] The thermosetting heat-resistant material using the cyanamide-maleimide compound has a problem in that it has a relatively large dielectric constant of about 3.5 compared to PTFE. Particularly in electronic component materials such as LSIs, it is desirable that the dielectric constant of the insulating material be small because it affects the signal transmission speed.

An object of the present invention is to provide a thermosetting resin composition that takes advantage of the heat resistance of the cyanamide-maleimide compound and has a low dielectric constant.

[Means for Solving the Problems] The present invention has been made to achieve the above object, and the gist thereof consists of a cyanamide compound represented by the general formula (I) % formula % (I) and a cyanamide compound represented by the general formula (II) ) (wherein Rf in formula 1 is a difunctional group having at least one aromatic ring and a fluorine-containing propylene group), and uses of the composition. be.

In order to lower the dielectric constant of cyanamide compounds and maleimide compounds, there are two possible methods: introducing a less polar aliphatic hydrocarbon chain into the molecule and introducing fluorine as a substituent.

In the former case, the dielectric constant decreases, but the heat resistance and flame retardance decrease significantly. On the other hand, the latter method of introducing fluorine reduces the dielectric constant and improves heat resistance.

Flame retardancy can be improved.

When heated, the fluorine-containing cyanamide compound and the fluorine-containing maleimide compound undergo a trimerization reaction to form heteroaromatic rings such as melamine rings, isomelamine rings, imide rings, etc., and complex three-dimensional crosslinking, resulting in a high-temperature dielectric constant of around 3. It is a material with excellent mechanical properties, dimensional stability, and heat resistance. Furthermore, since the crosslinking and curing reaction does not produce reaction by-products such as condensed water, it can be used as a mold material and various other structural materials. This is an advantage over heat-resistant insulating materials such as polyimide, polyimidazole, and polybenzothiazole.

Examples of the fluorine-containing cyanamide compound represented by the general formula (I) include 2,2-bis(4-(4-cyanamidophenoxy)phenyl]-1,1,1,3,3-hexafluoropropane, 2,2 -bis[4-(2-)-lifluoromethyl-4-cyanamidophenoxy)phenyl)-1,1,1
, 3,3,3-hexafluoropropane, 2,2-bis(4-(3-trifluoromethyl-4-cyanamidophenoxy)phenyl]-1°1.1,3..3,3-hexafluoropropane, 2゜2-bis[3-methyl-4-(
4-cyanamidophenoxy)phenyl]-1,1,1,
3,3,3-hexafluoropropane, 2,2-bis [
3-Methyl-4-(2-trifluoromethyl-4-cyanamidophenoxy)phenyl)-1,1,1,3,3,
3-hexafluoropropane, 2,2-bis[3-chloro-4(4-cyanamidophenoxy)phenyl)-1,
1゜1.3.3.3-hexafluoropropane, 2,2
-bis[3-chloro-4-(2-trifluoromethyl-
4-cyanamidophenoxy)phenyl)-1,1゜1.
3,3.3-hexafluoropropane, 2,2-bis[
3-Bromo-4-(4-cyanamidophenoxy)phenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-bromo-4-(2-trifluoromethyl) -4-cyanamidophenoxy)phenyl)-1
,1,1,3,3,3-hexafluoropropane,2,
2-bis[3-ethyl-4-(4-cyanamidophenoxy)phenyl)-1,1゜1.3,3.3-hexafluoropropane, 2,2-bis[3-ethyl-4-(2 −
Trifluoromethyl-4-cyanamidophenoxy)phenyl)-1,1゜1.3,3,3-hexafluoropropane, 2,2-bis[3-propyl-4-(4-cyanamidophenoxy)phenyl)- 1, 1, 1, 3, 3, 3
-hexafluoropropane, 2,2-bis[3-propyl-4-(2-trifluoromethyl-4-cyanamidophenoxy)phenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-isopropyl-4-(4-cyanamidophenoxy)phenyl]-1,
1,1,3,3,3-hexafluoropropane, 2.2
-bis[3-isopropyl-4-(2-trifluoromethyl-4-cyanamidophenoxy)phenyl)-1,1
, 1,3,3,3-hexafluoropropane, 2.2-
Bis[3-butyl-4-(4-cyanamidophenoxy)
phenyl]-1,1,1,3,3゜3-hexafluoropropane, 2,2-bis[3-butyl-4-(2-trifluoromethyl-4-cyanamidophenoxy)phenyl]-1,1 ,1,3,3゜3-hexafluoropropane, 2,2-bis[3゜5-dimethyl-4-(4-cyanamidophenoxy)phenyl)-1,1,1,3,3,3
-hexafluoropropane, 2,2-bis[3,5-dichloro-4=.(4-cyanamidophenoxy)phenyl)-,1,1°1.3,3,3-hexafluoropropane, 2, 2-bis[3,5-dichloro-4-(2-)-
Lifluoromethyl-4-cyanamidophenoxyphenyl]-1,1,1,3,3,3-hexafluoropropane 52.2-bis[3,5-dibromo-4-(4-cyanamidophenoxy)phenyl] -1, 1, 1, 3, 3,
3-hexafluoropropane, 2,2-bis[3,5-
dibromo-4-(2-)-lifluoromethyl-4-cyanamidophenoxy)phenyl]-1,1,1°3.3.
3-hexafluoropropane, 2,2-bis(4-(4
-cyanamidophenoxy)biphenyl]-1,1,1,
3,3-hexafluoropropane, 2゜2-bis(4-
(2-trifluoromethyl-4-cyanamidophenoxy)
biphenyl)-1,1,1,3,3゜3-hexafluoropropane, 2,2-bis[4-(3-trifluoromethyl-4-cyanamidophenoxy)biphenyl)-1,1
, 1,3,3,3-hexafluoropropane, 2,2-
Bis[3-methyl-4-(4-cyanamidophenoxy)
biphenyl]-1゜1.1,3,3,3-/\xafluoropropane, 2゜2-bis[3-methyl-4-(2-
Trifluoromethyl-4-cyanamidophenoxy)biphenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-chloro-4(4-cyanamidophenoxy)biphenyl)-1, 1, 1, 3, 3, 3
-hexafluoropropane, 2,2-bis[3-chloro-4-(2-)-lifluoromethyl-4-cyanamidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane ,2,2-bis[3-bromo4
-(4-cyanamidophenoxy)biphenyl)-1,1
, 1,3,3,3-hexafluoropropane, 2,2-
Bis[3-bromo-4-(2-trifluoromethyl-4
-cyanamidophenoxy)biphenyl)-1,1,1,
3,3,3-hexafluoropropane, 2,2-bis [
3-ethyl-4-(4-cyanamidophenoxy)biphenyl)-1,1,1,3゜3.3-hexafluoropropane, 2,2-bis[3-ethyl-4-(2-trifluoromethyl) -4-cyanamidophenoxy)biphenyl)
-1,1,1゜3.3.3-hexafluoropropane,
2,2-bis[3-propyl-4-(4-cyanamidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-propyl-
4=(2-trifluoromethyl-4-cyanamidophenoxy)biphenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-isopropyl-
4-(4-cyanamidophenoxy)biphenyl)-1,
1,1,3,3,3-hexafluoropropane, 2,2
-bis[3-isopropyl-4-(2-trifluoromethyl-4-cyanamidophenoxy)biphenyl)-1,
1,1,3,3,3-hexafluoropropane, 2,2
-bis[3-butyl-4-(4-cyanamidophenoxy)biphenyl)-1,1゜1.3,3.3-hexafluoropropane, 2,2-bis[3-butyl-4-(2-
trifluoromethyl-4-cyanamidophenoxy)biphenyl]-1゜1.1,3,3.3-hexafluoropropane, 2゜2-bis[3,5-dimethyl-4-(4-
Cyanamidophenoxy)biphenyl]-4,1,1,3
, 3,3-hexafluoropropane, 2,2-bis[3
,5-dichloro-4-(4-cyanamidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3,5-dichloro-4-(2
-trifluoromethyl-4-cyanamidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3,5-dibromo-4-(4
-cyanamidophenoxy)biphenyl)-1,1,1,
3,3,3-hexafluoropropane, 2,2-bis [
3,5-dibromo-4-(2-trifluoromethyl-4
-cyanamidophenoxy)biphenyl)-1,1,1,
Examples include 3,3,3-hexafluoropropane.

Furthermore, examples of the fluorine-containing maleimide compound represented by the general formula (II) include 2,2-bisC4-C4-maleimidoenoxy)phenyl)-1,1,1,3,3-hexafluoropropane, 2,2 -bisC4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl>1.1,1,
3,3.3-hexafluoropropane, 2,2-bisC
4-C3-trifluoromethyl-4-maleimidophenoxy)phenyl]-1,1゜1.3,3.3-hexafluoropropane, 2,2-bis[3-methyl-4-(4-
maleimidophenoxy)phenyl)-1,1,1,3,
3,3-hexafluoropropane, 2,2-bis[3-
Methyl-4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl)-1,1,1,3,3,3-
Hexafluoropropane, 2,2-bis[3-chloro-
4(4-maleimidophenoxy)phenyl]-1,1,
1゜3.3.3-hexafluoropropane, 2,2-bis[3-chloro-4-(2-trifluoromethyl-4-
maleimidophenoxy)phenyl)-1,1,1゜3.
3.3-hexafluoropropane, 2.2-bis[3-
Bromo-4-(4-maleimidophenoxy)phenyl)
-1,1,1,3,3,3-hexafluoropropane,
2,2-bis(3-bromo-4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl)-1,
1,1,3,3,3-hexafluoropropane, 2,2
-bis[3-ethyl-4-(4maleimidophenoxy)
phenyl]-1,1,1,3゜3.3-hexafluoropropane, 2,2-bis[3-ethyl-4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl)-1,1 ,1゜3.3.3-hexafluoropropane, 2,2-bis[3-propyl-4-(4-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoro Propane, 2,2-bis[3-propyl-
4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-isopropyl-4
-(4-maleimidophenoxy)phenyl]-1,1,
1,3,3,3-hexafluoropropane, 2,2-bis[3-isopropyl-4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl]-1,1,1
,3,3,3-hexafluoropropane, 2,2-bis[3-butyl-4-(4-maleimidophenoxy)phenyl)-1,1,1,3,3゜3-hexafluoropropane, 2,2-bis[3-butyl-4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl)-
1,1,1,3,3゜3-hexafluoropropane, 2
,2-bis[3゜5-dimethyl-4-(4-maleimidophenoxy)phenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3,5-dichloro- 4-(4-maleimidophenoxy)phenyl)-1
, 1°1.3,3,3-hexafluoropropane, 2.
2-bis[3,5-dichloro-4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl]-1,
1,1,3,3,3-hexafluoropropane.

2.2-Bis[3,5-dibromo-4-(4-maleimidophenoxy)phenyl)-1,1,1,3,3,3-
Hexafluoropropane, 2,2-bis(3,5-dibromo-4-(2-trifluoromethyl-4=maleimidophenoxy)phenyl)-1,1,1゜3.3.3-hexa Fluoropropane, 2,2-bis(4-(4-maleimidophenoxy)biphenyl)-1,1,1,3,3
-hexafluoropropane, 2゜2-bis(4-(2-
Trifonimethyl-4-maleimidophenoxy)biphenyl)-1,1,1,3,3゜3-hexafluoropropane, 2,2-bis[4-(3-trifluoromethyl-4
-maleimidophenoxy)biphenyl]-1,1,1,
3,3,3-hexafluoropropane, 2,2-bis[
3-Methyl-4-(4-maleimidophenoxy)biphenyl]-1゜1.1,3,3,3-hexafluoropropane, 2゜2-bis[3-methyl-4-(2-trifluoromethyl- 4-Maleimidophenoxy)biphenyl]
-1,1,1,3,3,3-hexafluoropropane,
2,2-bis[3-chloro-4(4-maleimidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-chloro-4-(
2-trifluoromethyl-4-maleimidophenoxy)
biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-bromo-4-(4-maleimidophenoxy)biphenyl)-1,1,1,3,
3,3-hexafluoropropane, 2,2-bis[3-
Bromo-4-(2-)-lifluoromethyl-4-maleimidophenoxy)biphenyl)-1,1,1,3,3,
3-hexafluoropropane, 2,2-bis[3-ethyl-4-(4-maleimidophenoxy)biphenyl)-
1,1,1,3゜3.3-hexafluoropropane, 2
,2-bis[3-ethyl-4-(2-)-lifluoromethyl-4-maleimidophenoxy)biphenyl)-1,
1,1゜3.3.3-hexafluoropropane, 2,2
-bis[3-propyl-4-(4-maleimidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-propyl-4-(
2-trifluoromethyl-4-maleimidophenoxy)
Biphenylgo 1.1,1,3,3.3-hexafluoropropane, 2,2-bis[3-isopropyl-4-(
4-maleimidophenoxy)biphenyl]-1,1,1
,3,3,3-hexanehexafluoropropane,2,
2-bis[3-butyl-4-(4-maleimidophenoxy)biphenyl]-1゜1.1,3,3.3-hexafluoropropane, 2.2-bis(3-butyl-4-(2
-trifluoromethyl-4-maleimidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3,5-dimethyl 4-(4-
maleimidophenoxy)biphenyl]-1,1,1,3
, 3,3-hexafluoropropane, 2,2-bis[3
,5-dichloro-4-(4-maleimidophenoxy)biphenyl]-1゜1.1,3,3,3-hexafluoropropane, 2.2-bis[3,5-dichloro-4-(2
-trifluoromethyl-4-maleimidophenoxy)biphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3,5-dibromo-4-(4
-maleimidophenoxy)biphenyl)-1,1,1,
3,3,3-hexafluoropropane, 2,2-bis [
3,5-dibromo-4-(2-trifluoromethyl-4
-maleimidophenoxy)biphenyl)-1,1,1,
Examples include 3,3°3-hexafluoropropane.

A fluorine-containing cyanamide compound represented by the general formula (I),
The blending ratio of the fluorine-containing maleimide compound represented by general formula (II) is preferably 3 to 7 moles per 1 mole of the former. Outside this range, moldability becomes a problem, which is not preferable.

A polyfunctional epoxy compound containing a halogen atom can be blended into the compositions of the above general formulas (I) and (If), if necessary. In view of the relative dielectric constant, the blending ratio is preferably 10 parts by weight or less based on 100 parts by weight of the composition of the present invention.

The composition of the present invention can be prepared in the pre-reacted B state depending on the purpose;
It can be used as a so-called prepolymer. For example, the composition in state B can be made into a varnish using a solvent. Furthermore, it can be impregnated into a fibrous base material (for example, glass cloth) to form a prepreg and used for coil insulating materials, laminated materials, etc.

Examples of the solvent used include acetone, methyl ethyl ketone, methyl isobutyl ketone, dioxane, dimethyl dioxane, N,N-dimethylformamide, and N-methyl-2-pyrrolidone.

The composition of the present invention is characterized in that it can be cured without using a curing catalyst, but a curing catalyst may be used to further promote the reaction. Such a catalyst is tetramethylbutanediamine.

Benzyldimethylamine, 2,4.6-tris(dimethylaminophenol), guanidine, tetramethylguanidine, 2-methylimidazole, 2゜5-dimethyl-
It is preferable to use 0.1 to 5 parts by weight of 2,5-t-butylperoxine (hexyne-3) or the like per 100 parts by weight of the composition.

In addition, known inorganic fillers, flame retardants, flexibilizers, antioxidants, pigments, coupling agents, mold release agents, etc. may be blended within the range that does not impair the purpose of the present invention.

[Function] The reason why it is possible to obtain a cured product with a low dielectric constant by using the composition of the present invention is thought to be because the specific molar volume increases by replacing hydrogen with fluorine.

Further, it is believed that the carbon-fluorine bond has a larger bond energy of about 100 kj/mo+2 than the carbon-carbon bond, and therefore can improve the thermal decomposition temperature.

In particular, a fluorine-containing propylene group having a trifluoromethyl group has a high fluorine content of 76%, and can achieve a low dielectric constant.

[Example code] The present invention will be explained based on examples.

[Example 1] 2.2-bis[4-(4-cyanamidophenoxy)phenyl)-1,1,1,3,3,3-hexafluoropropane (manufactured by Manac, USA: CF-6): 20 g ,2
．． 2-bis[4-(4-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane (manufactured by Hitachi Chemical): Dissolve 80 g in 100 g of methyl isobutyl ketone and dissolve for 60 minutes. Prepolymerization was carried out under reflux. After cooling to room temperature, remove the solvent by vacuum drying,
A powdered sample was obtained.

2 powdery sample was press-molded using a 2 mm thick spacer and cured to create a resin plate. The molding conditions were such that after melting the powdered sample at 150°C,
The temperature was raised to 0°C, and the mixture was heated and pressed for 120 minutes to cure.

[Example 2] 2.2-bis[4-(2-trifluoromethyl-4-cyanamidophenoxy)phenyl)-1,1,1°3.3
．． 3-hexafluoropropane (manufactured by Manac, USA: C
F-12): 20g, 2,2-bis[4-(2-trifluoromethyl-4-maleimidophenoxy)phenyl]
-1,1,1,3,3,3-hexafluoropropane (
A resin plate was produced in the same manner as in Example 1, except that 80 g of MF-12 (manufactured by Central Glass) was used.

[Example 3] 20 g of 2.2-bis(4-(4-cyanamidophenoxy)phenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-(4- A resin plate was prepared in the same manner as in Example 1, except that 80 g of maleimidophenoxy)phenyl-1,1,1,3,3,3-hexafluoropropane was dissolved in 200 g of acetone.

Table 1 shows the measurement results of the dielectric constant, thermal expansion coefficient 9 bending strength, and thermal decomposition temperature of each sample plate of Examples 1 to 3.

Table 1 The relative dielectric constant, thermal expansion coefficient, and bending strength shown in Table 1 are in accordance with JIS-6.
Measured according to 911. In addition, the thermal decomposition temperature was carried out at a heating rate of 5° C./min and 100 rr + I2/min in air. [Comparative Example 1] 4.4-methylenebis(0-methylphenylcyanamide ): 80g, N,N-dimethylformamide 100g
were mixed and refluxed at 120°C for 20 minutes to form a prepolymer. After cooling to room temperature, remove the solvent by vacuum drying,
A powdered sample was obtained.

The above powdered sample was press-molded using a 2 mm thick spacer to create a cured resin plate. In addition.

The molding conditions were after melting the powdered sample at 150°C.

The temperature was raised to 250° C., heated for 120 minutes, and pressurized to create a resin plate.

Table 1 also shows the measurement results of the dielectric constant, thermal expansion coefficient, bending strength, and thermal decomposition temperature of the sample plate.

As is clear from Table 1, the resin composition of the present invention has a dielectric constant of 3 or less, and is superior in bending strength and thermal decomposition temperature, compared to the comparative example.

[Effects of the Invention] The fluorine-containing resin composition of the present invention has the effect of lowering the dielectric constant of a cured product obtained by incorporating fluorine, and has excellent heat resistance and high-temperature mechanical properties.
It is suitable as a molding material and an insulating material for various electrical devices.

Claims (1)

[Claims] 1. A cyanamide compound represented by the general formula (I) NCHN-Rf-NHCN (I) and a maleimide represented by the general formula (II) ▲There are numerical formulas, chemical formulas, tables, etc.▼(II) A thermosetting resin composition comprising a compound (wherein Rf is a bifunctional group having at least one aromatic ring and a fluorine-containing propylene group). 2. A cyanamide compound represented by general formula (I),
The thermosetting resin composition containing the maleimide compound represented by the general formula (II) (wherein Rf is a bifunctional group having at least one aromatic ring and a fluorine-containing propylene group) is in the B state. Characteristic prepolymer. 3. A fibrous base material and a resin impregnated into the fibrous base material are a cyanamide compound represented by the general formula (I) and a maleimide compound represented by the general formula (II) (wherein Rf
consists of a thermosetting resin composition containing at least one aromatic ring and a difunctional group having a fluorine-containing propylene group;
A prepreg characterized by being in a state of 4. A cyanamide compound represented by general formula (I);
Impregnating a fibrous base material with a thermosetting resin composition containing a maleimide compound represented by general formula (II) (wherein Rf is a bifunctional group having at least one aromatic ring and a fluorine-containing propylene group), A method for manufacturing a laminate, which comprises laminating a plurality of the fibrous base materials and curing them under pressure and heat.