Aromatic polyether, resin composition, and composite material

Abstract

This aromatic polyether includes a structural unit represented by formula (a) and a structural unit represented by formula (b), and has a radical amount of 6.5×1015-9.0×1017(spin / g) at 25°C as measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance.

Description

Aromatic polyether, resin composition, and composite material

[0001] The present invention relates to an aromatic polyether, a resin composition, and a composite material. Specifically, the present invention relates to an aromatic polyether, a resin composition, and a composite material that exhibit excellent adhesion to reinforcing fibers and have excellent moldability.

[0002] Patent Document 1 discloses a specific aromatic polyether produced by adding a component having a specific polymerization catalytic activity to a reaction system, and also discloses the use of this aromatic polyether mixed with a reinforcing material or filler such as glass fiber, carbon fiber, aramid fiber, calcium carbonate, or calcium silicate.

[0003] Patent Document 2 discloses an aromatic polyether copolymer having a specific structure.

[0004] JP-A No. 64-065129 JP-A No. 03-181519

[0005] However, it has been found that there is room for further improvement in conventional aromatic polyethers such as those described in Patent Documents 1 and 2, from the viewpoint of improving adhesion to reinforcing fibers and from the viewpoint of molding processability.

[0006] An object of the present invention is to provide an aromatic polyether, a resin composition, and a composite material that can exhibit excellent adhesion to reinforcing fibers and also have excellent moldability.

[0007] As a result of extensive research, the present inventors have found that aromatic polyethers containing a specific structure have excellent adhesion to reinforcing fibers and can improve molding processability, and have thus completed the present invention. According to the present invention, the following aromatic polyethers and the like can be provided: 1. An aromatic polyether containing a structural unit represented by the following formula (a) and a structural unit represented by the following formula (b), which has a radical content of 6.5 x 10 at 25°C, measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance: １５ ~9.0 x 10 １７ (spin / g) of an aromatic polyether. 2. The aromatic polyether according to 1 above, which contains a structural unit represented by the following formula (b') as the structural unit represented by the formula (b): 3. The aromatic polyether according to 1 or 2, having a glass transition temperature (Tg) of 140°C or higher. 4. The aromatic polyether according to any one of 1 to 3, having a melting point (Tm) of 330°C or lower. 5. The aromatic polyether according to any one of 1 to 4, having a difference (Δ(Tm-Tg)) between the melting point (Tm) and the glass transition temperature (Tg) of 185°C or lower. 6. The aromatic polyether according to any one of 1 to 5, having a crystallinity (%) of 33% or lower. 7. The aromatic polyether according to any one of 1 to 6, having a crystallinity (%) of 5% or higher and 30% or lower. 8. The aromatic polyether according to any one of 1 to 7, which is a copolymer of 4,4'-dichlorobenzophenone (DCBP), dihalogenobenzonitrile (DXBN), and hydroquinone (HQ). 9. The aromatic polyether according to 8, wherein the dihalogenobenzonitrile includes 2,6-dichlorobenzonitrile (DCBN). 10. The aromatic polyether according to 8 or 9, wherein the molar ratio (DXBN / (DCBP+DXBN)) of the dihalogenobenzonitrile (DXBN) to the total amount of the 4,4'-dichlorobenzophenone (DCBP) and the dihalogenobenzonitrile (DXBN) is 5 to 40 mol %. 11. The aromatic polyether according to any one of 1 to 10, wherein 50 mass % or more of the aromatic polyether is the structural unit represented by formula (a) and the structural unit represented by formula (b). 12. An aromatic polyether according to any one of 1 to 11, and an amorphous resin, or an aromatic polyether comprising a structural unit represented by the following formula (a) and a structural unit represented by the following formula (b), and an amorphous resin, wherein the amount of radicals at 25°C measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance is 6.5 x 10 １５ ~9.0 x 10 １７ (spin / g). 13. A composite material comprising the aromatic polyether according to any one of 1 to 11 or the resin composition according to 12, and 0.01 to 500 parts by mass of reinforcing fibers per 100 parts by mass of the aromatic polyether or resin composition. 14. The composite material according to 13, wherein the reinforcing fibers comprise one or more fibers selected from the group consisting of carbon fibers, glass fibers, and aramid fibers. 15. A method for producing the aromatic polyether according to any one of 1 to 11, comprising reacting 4,4'-dichlorobenzophenone (DCBP), dihalogenobenzonitrile (DXBN), and hydroquinone (HQ).

[0008] According to the present invention, it is possible to provide an aromatic polyether, a resin composition, and a composite material that can exhibit excellent adhesion to reinforcing fibers and have excellent moldability.

[0009] The aromatic polyether, resin composition, and composite material of the present invention are described in detail below. In this specification, "x to y" represents a numerical range of "x or more and y or less." The upper and lower limits of the numerical ranges can be combined arbitrarily. Furthermore, among the individual embodiments of the aspects of the present invention described below, two or more embodiments that are not mutually contradictory can be combined, and an embodiment combining two or more embodiments is also an embodiment of the aspects of the present invention.

[0010] 1. Aromatic Polyether The aromatic polyether according to one embodiment of the present invention comprises a structural unit represented by the following formula (a) and a structural unit represented by the following formula (b), and has a radical amount of 6.5 × 10 at 25°C, measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance: １５ ~9.0 x 10 １７ (spin / g).

[0011]

[0012] The aromatic polyether according to this embodiment can exhibit excellent adhesion to reinforcing fibers and also exhibit excellent molding processability. Regarding molding processability, in particular, the processing temperature can be lowered and dimensional stability can be improved. While the reason for such effects is not entirely clear, it is presumed that a new structure with adhesive properties to reinforcing fibers is formed due to the effect of the high concentration of radicals in the aromatic polyether. Furthermore, the aromatic polyether according to this embodiment can maintain its glass transition temperature (Tg) by including a structural unit represented by formula (a). This maintains heat resistance. Furthermore, the aromatic polyether according to this embodiment can lower its melting point (Tm) without lowering its glass transition temperature by including a structural unit represented by formula (b). This allows the processing temperature during molding to be lowered while maintaining heat resistance. Furthermore, the aromatic polyether according to this embodiment can reduce its crystallinity by including a structural unit represented by formula (b). This prevents warping of molded articles when subjected to press molding, etc. Furthermore, shrinkage during the cooling process during molding can be suppressed (dimensional stability can be improved), preventing the formation of voids inside the molded article. This crystallinity can also be controlled by adjusting the ratio of the structural unit represented by formula (b) to the structural unit represented by formula (a) (by increasing this ratio, the crystallinity can be further reduced).

[0013] In one embodiment, the radical content of the aromatic polyether is 6.5×10 １５ spin / g or more, 7.0×10 １５ spin / g or more, 8.0×10 １５ spin / g or more, 9.0×10 １５ spin / g or more, 1.0×10 １６ spin / g or more, and １７ spin / g or less, 7.0×10 １７ spin / g or less, 5.0×10 １７ spin / g or less or 3.0 x 10 １７ The amount of radicals in the aromatic polyether is 6.5×10 １５On the other hand, if the radical amount of the aromatic polyether is less than 9.0 × 10 １７ If the value exceeds 10 ...

[0014] The aromatic polyether can also be said to be a copolymer of a structural unit represented by formula (a) and a structural unit represented by formula (b). In one embodiment, the copolymer is a random copolymer, an alternating copolymer, or a block copolymer, and is preferably a random copolymer.

[0015] In one embodiment, the aromatic polyether contains a structural unit represented by the following formula (b') as the structural unit represented by formula (b).

[0016]

[0017] In one embodiment, in the aromatic polyether, the proportion of the structural unit represented by formula (b') among the structural units represented by formula (b) is 10 mol% or more, 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, 95 mol% or more, 98 mol% or more, 99 mol% or more, 99.5 mol% or more, or 100 mol%. Note that in the aromatic polyether, when the proportion of the structural unit represented by formula (b') among the structural units represented by formula (b) is 100 mol%, it may contain structural units other than the structural unit represented by formula (b') as inevitable impurities.

[0018] In one embodiment, in the aromatic polyether, the proportion of the structural unit represented by formula (b') among the structural units represented by formula (b) is 10 mol% or more and 100 mol% or less, 20 mol% or more and 100 mol% or less, 30 mol% or more and 100 mol% or less, 40 mol% or more and 100 mol% or less, 50 mol% or more and 100 mol% or less, 60 mol% or more and 100 mol% or less, 70 mol% or more and 100 mol% or less, 80 mol% or more and 100 mol% or less, 90 mol% or more and 100 mol% or less, 95 mol% or more and 100 mol% or less, 98 mol% or more and 100 mol% or less, 99 mol% or more and 100 mol% or less, 99.5 mol% or more and 100 mol% or less.

[0019] In one embodiment, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, 99% by mass or more, 99.5% by mass or more, or substantially 100% by mass of the aromatic polyether are structural units represented by formula (a) and structural units represented by formula (b), or structural units represented by formula (a) and structural units represented by formula (b').

[0020] In one embodiment, the glass transition temperature (Tg) of the aromatic polyether is 140°C or higher, 145°C or higher, or 150°C or higher. The upper limit is not particularly limited, and may be, for example, 165°C or lower. When the aromatic polyether has a glass transition temperature (Tg) of 140°C or higher, it can exhibit good heat resistance in various applications. The glass transition temperature (Tg) of the aromatic polyether is a value measured by the method described in the examples.

[0021] In one embodiment, the glass transition temperature (Tg) of the aromatic polyether is 140°C or more and 165°C or less, 145°C or more and 165°C or less, or 150°C or more and 165°C or less.

[0022] In one embodiment, the melting point (Tm) of the aromatic polyether is 330°C or less, 325°C or less, 320°C or less, 315°C or less, 310°C or less, 305°C or less, 300°C or less, 295°C or less, 290°C or less, 285°C or less, 280°C or less, 275°C or less, 270°C or less, or 265°C or less. The lower limit is not particularly limited and may be, for example, 250°C or more. When the melting point (Tm) of the aromatic polyether is 330°C or less, the heating temperature during molding can be lowered, thereby preventing thermal degradation of the aromatic polyether and improving energy efficiency during molding. As a result, the suitability of the aromatic polyether for molding processability is improved. The melting point (Tm) of the aromatic polyether is a value measured by the method described in the examples.

[0023] In one embodiment, the melting point (Tm) of the aromatic polyether is 250°C or higher and 330°C or lower, 250°C or higher and 325°C or lower, 250°C or higher and 320°C or lower, 250°C or higher and 315°C or lower, 250°C or higher and 310°C or lower, 250°C or higher and 305°C or lower, 250°C or higher and 300°C or lower, 250°C or higher and 295°C or lower, 250°C or higher and 290°C or lower, 250°C or higher and 285°C or lower, 250°C or higher and 280°C or lower, 250°C or higher and 275°C or lower, 250°C or higher and 270°C or lower, or 250°C or higher and 265°C or lower.

[0024] In one embodiment, the difference (Δ(Tm-Tg)) between the melting point (Tm) and the glass transition temperature (Tg) of the aromatic polyether is 185°C or less, 180°C or less, 170°C or less, 165°C or less, 160°C or less, 155°C or less, 150°C or less, 145°C or less, 140°C or less, 135°C or less, 130°C or less, or 125°C or less. A small difference means that the above-mentioned effect of "lowering the melting point (Tm) without lowering the glass transition temperature (Tg)" is large. The lower limit of Δ(Tm-Tg) is not particularly limited, and is, for example, 100°C or more or 110°C or more.

[0025] In one embodiment, the difference between the melting point (Tm) and the glass transition temperature (Tg) of the aromatic polyether (Δ(Tm-Tg)) is 100°C or more and 185°C or less, 100°C or more and 180°C or less, 100°C or more and 170°C or less, 110°C or more and 170°C or less, 110°C or more and 165°C or less, 110°C or more and 150°C or less, 110°C or more and 130°C or less, or 110°C or more and 125°C or less.

[0026] In one embodiment, the crystallinity of the aromatic polyether is 33% or less, 32% or less, 31% or less, 30% or less, 29% or less, 28% or less, 27% or less, 26% or less, 25% or less, 24% or less, 23% or less, 22% or less, 21% or less, 20% or less, 19% or less, 18% or less, 17% or less, 16% or less, or 15% or less. The lower limit is not particularly limited and may be, for example, 5% or more. When the crystallinity of the aromatic polyether is 5% or more, chemical resistance is easily obtained. When the crystallinity of the aromatic polyether is 33% or less, warping of the molded article can be prevented when subjected to press molding or the like. Furthermore, shrinkage during the cooling process during molding is suppressed, preventing the formation of voids inside the molded article. The crystallinity (%) of the aromatic polyether is a value measured by the method described in the examples.

[0027] In one embodiment, the complex viscosity of the aromatic polyether at 360 ° C. is 450 Pa s or more, 500 Pa s or more, 600 Pa s or more, 700 Pa s or more, 800 Pa s or more, 900 Pa s or more, 1000 Pa s or more, 1100 Pa s or more, or 1200 Pa s or more, and is 7000 Pa s or less, 6000 Pa s or less, 5000 Pa s or less, 4500 Pa s or less, 4000 Pa s or less, 3500 Pa s or less, 3000 Pa s or less, or 2800 Pa s or less. From one perspective, the complex viscosity can be said to be an indicator of the molecular weight of the aromatic polyether. If the complex viscosity of the aromatic polyether at 360 ° C. is 450 Pa s or more, the aromatic polyether has a sufficiently high molecular weight. Furthermore, even in such highly molecular weight aromatic polyethers, by including the structural unit represented by formula (b) as described above, the melting point (Tm) can be lowered without lowering the glass transition temperature (Tg). Therefore, the processing temperature during molding can be lowered while maintaining heat resistance. Furthermore, if the complex viscosity of the aromatic polyether at 360°C is 7000 Pa s or less, the aromatic polyether will exhibit favorable fluidity when melted, improving its suitability for various moldings. The complex viscosity of the aromatic polyether at 360°C is a value measured by the method described in the Examples.

[0028] In one embodiment, the complex viscosity of the aromatic polyether at 360°C is 450 Pa·s or more and 7000 Pa·s or less, 500 Pa·s or more and 7000 Pa·s or less, 600 Pa·s or more and 6000 Pa·s or less, 700 Pa·s or more and 5000 Pa·s or less, 800 Pa·s or more and 4500 Pa·s or less, 900 Pa·s or more and 4000 Pa·s or less, 1000 Pa·s or more and 3500 Pa·s or less, 1100 Pa·s or more and 3000 Pa·s or less, or 1200 Pa·s or more and 2800 Pa·s or less.

[0029] In one embodiment, the aromatic polyether is a copolymer of 4,4'-dichlorobenzophenone (DCBP), dihalogenobenzonitrile (DXBN), and hydroquinone (HQ). In one embodiment, the aromatic polyether is a copolymer containing 4,4'-dichlorobenzophenone (DCBP), dihalogenobenzonitrile (DXBN), and hydroquinone (HQ) as monomer components. The structural unit represented by formula (a) may be a linker of 4,4'-dichlorobenzophenone (DCBP) and hydroquinone (HQ). The structural unit represented by formula (b) may be a linker of dihalogenobenzonitrile (DXBN) and hydroquinone (HQ).

[0030] 4,4'-Dichlorobenzophenone (DCBP) gives an aromatic polyether with a radical content of 6.5 × 10 １５ ~9.0 x 10 １７ (spin / g). As a result, the adhesion of the aromatic polyether to the reinforcing fiber can be improved. Meanwhile, dihalogenobenzonitrile (DXBN) has excellent reactivity with hydroquinone, and therefore can efficiently promote the reaction to form the structural unit represented by formula (b).

[0031] In one embodiment, the dihalogenobenzonitrile contains 2,6-dichlorobenzonitrile (DCBN). This significantly reduces the melting point (Tm) without reducing the glass transition temperature (Tg). In one embodiment, the proportion of 2,6-dichlorobenzonitrile (DCBN) in the dihalogenobenzonitrile is 5 mol% or more, 10 mol% or more, 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, 95 mol% or more, 98 mol% or more, 99 mol% or more, 99.5 mol% or more, or 100 mol%. In addition, when the proportion of 2,6-dichlorobenzonitrile (DCBN) in the dihalogenobenzonitrile is 100 mol %, dihalogenobenzonitriles other than 2,6-dichlorobenzonitrile (DCBN) may be contained as inevitable impurities.

[0032] By using 2,6-dichlorobenzonitrile (DCBN) as the dihalogenobenzonitrile, the structural unit represented by formula (b') can be formed as a linker of 2,6-dichlorobenzonitrile (DCBN) and hydroquinone (HQ).

[0033] As an example, the copolymerization reaction of 4,4'-dichlorobenzophenone (DCBP), 2,6-dichlorobenzonitrile (DCBN) and hydroquinone (HQ) is shown below.

[0034]

[0035] In the above formula, "(r)" in the product means that the structural units on both sides of it (corresponding to the structural unit represented by formula (a) and the structural unit represented by formula (b')) are randomly copolymerized. There are no particular limitations on n (the number of structural units represented by formula (a)) and m (the number of structural units represented by formula (b')) in the product. In one embodiment, m+n is 10 to 100. In one embodiment, m is 1 to 99 or 1 to 40. In one embodiment, n is 1 to 99 or 6 to 60. The explanation given for m (the number of structural units represented by formula (b')) can also be applied to the number of structural units represented by formula (b). The values ​​of n and m can be derived from the terminal structure and composition ratio measured by NMR.

[0036] In one embodiment, the molar ratio of the dihalogenobenzonitrile (DXBN) to the total amount of the 4,4'-dichlorobenzophenone (DCBP) and the dihalogenobenzonitrile (DXBN) (DXBN / (DCBP+DXBN)) is 1 mol% or more, 2 mol% or more, 3 mol% or more, 4 mol% or more, 5 mol% or more, 6 mol% or more, 7 mol% or more, or 8 mol% or more, and is 99 mol% or less, 90 mol% or less, 80 mol% or less, 70 mol% or less, 60 mol% or less, 50 mol% or less, 40 mol% or less, 39 mol% or less, 38 mol% or less, 37 mol% or less, 30 mol% or less, or 20 mol% or less. When the molar ratio (DXBN / (DCBP+DXBN)) is 5 mol% or more, the effect of lowering the melting point (Tm) without lowering the glass transition temperature (Tg) is significantly exhibited. Furthermore, when the molar ratio (DXBN / (DCBP+DXBN)) is 40 mol% or less, chemical resistance can be improved. Therefore, it is particularly preferable that the molar ratio (DXBN / (DCBP+DXBN)) is 5 to 40 mol%. This molar ratio (DXBN / (DCBP+DXBN)) can be measured by the method described in the Examples. This molar ratio (DXBN / (DCBP+DXBN)) can correspond to the molar ratio of each monomer component in the aromatic polyether. Furthermore, this molar ratio (DXBN / (DCBP+DXBN)) can correspond to the molar ratio of the structural units represented by formula (b) to the total amount of the structural units represented by formula (a) and formula (b) (in other words, the ratio m / (n+m) in the copolymerization reaction formula shown above). Furthermore, this molar ratio (DXBN / (DCBP+DXBN)) can correspond to the molar ratio of the amounts of each monomer charged in the copolymerization reaction to produce an aromatic polyether.

[0037] In one embodiment, the molar ratio of the dihalogenobenzonitrile (DXBN) to the total amount of the 4,4'-dichlorobenzophenone (DCBP) and the dihalogenobenzonitrile (DXBN) (DXBN / (DCBP+DXBN)) is 1 mol% to 99 mol%, 2 mol% to 90 mol%, 3 mol% to 80 mol%, 4 mol% to 70 mol%, 5 mol% to 60 mol%, 6 mol% to 50 mol%, 7 mol% to 40 mol%, 7 mol% to 39 mol%, 7 mol% to 38 mol%, 8 mol% to 37 mol%, or 8 mol% to 30 mol%.

[0038] In one embodiment, the reaction system (also referred to as "reaction mixture") for producing the aromatic polyether contains a solvent in addition to the above-mentioned monomers. The solvent is not particularly limited, and for example, an aprotic polar solvent can be used. Examples of the aprotic polar solvent include N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dipropylacetamide, N,N-dimethylbenzoic acid amide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-isopropyl-2-pyrrolidone, N-isobutyl-2-pyrrolidone, N-n-propyl-2-pyrrolidone, N-n-butyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, and N-methyl-3-methyl-2-pyrrolidone. , N-ethyl-3-methyl-2-pyrrolidone, N-methyl-3,4,5-trimethyl-2-pyrrolidone, N-methyl-2-piperidone, N-ethyl-2-piperidone, N-isopropyl-2-piperidone, N-methyl-6-methyl-2-piperidone, N-methyl-3-ethylpiperidone, dimethyl sulfoxide, diethyl sulfoxide, 1-methyl-1-oxosulfolane, 1-ethyl-1-oxosulfolane, 1-phenyl-1-oxosulfolane, N,N'-dimethylimidazolidinone, diphenyl sulfone, etc. Among these, diphenyl sulfone is particularly preferred.

[0039] The reaction mixture may contain one or more solvents, and it is particularly preferred that the reaction mixture contains only one solvent (single solvent), which simplifies the process.

[0040] In one embodiment, the reaction mixture contains a base. The reaction is promoted by including a base in the reaction mixture. The base is not particularly limited, and examples thereof include alkali metal salts. Examples of alkali metal salts include alkali metal carbonates and alkali metal bicarbonates. Examples of alkali metal carbonates include potassium carbonate, lithium carbonate, rubidium carbonate, and cesium carbonate. Examples of alkali metal bicarbonates include lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, rubidium bicarbonate, and cesium bicarbonate. Among these, potassium carbonate is particularly preferred. These bases may be used alone or in combination of two or more.

[0041] In one embodiment, the reaction mixture is heated. The maximum temperature (maximum temperature reached) of the reaction mixture during the reaction is not particularly limited as long as it is a temperature at which an aromatic polyether is produced, and may be, for example, 250 to 350°C.

[0042] 2. Resin Composition A resin composition (also referred to as "alloy") according to one aspect of the present invention comprises an aromatic polyether according to one aspect of the present invention and an amorphous resin (first embodiment), or an aromatic polyether comprising a structural unit represented by formula (a) and a structural unit represented by formula (b), and an amorphous resin, and has a radical amount of 6.5 x 10 at 25°C measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance. １５ ~9.0 x 10 １７(spin / g) (Second embodiment). In the second embodiment, it is sufficient that the resin composition satisfies the radical amount condition. Here, the aromatic polyether itself may or may not satisfy the radical amount condition. For the aromatic polyether of the second embodiment, the explanation given for the aromatic polyether according to one aspect of the present invention is applicable, except that the radical amount condition is not essential. Furthermore, for the radical amount of the resin composition, the explanation given for the radical amount of the aromatic polyether according to one aspect of the present invention is applicable.

[0043] The resin composition according to this embodiment can exhibit excellent adhesion to reinforcing fibers and also has excellent molding processability, particularly allowing the processing temperature to be lowered and improving dimensional stability.

[0044] Examples of amorphous resins include resins that do not show a clear endothermic peak but show a stepwise endothermic change in differential scanning calorimetry (DSC).

[0045] In one embodiment, the amorphous resin comprises one or more selected from the group consisting of polyetherimide (PEI), polyethersulfone (PES), polyphenylene ether (PPE), polysulfone (PSU), and polyimide (PI).

[0046] In one embodiment, the amorphous resin comprises polyetherimide (PEI).

[0047] In one embodiment, the content of the amorphous resin in the resin composition is 5 to 300 parts by mass relative to 100 parts by mass of the aromatic polyether. It may be 20 to 250 parts by mass, 30 to 200 parts by mass, 40 to 150 parts by mass, 50 to 100 parts by mass, 5 to 50 parts by mass, or 5 to 25 parts by mass.

[0048] The content of the amorphous resin in the resin composition may be 5 parts by mass or more, 10 parts by mass or more, 20 parts by mass or more, 30 parts by mass or more, 40 parts by mass or more, 50 parts by mass or more, 100 parts by mass or more, or 200 parts by mass or more, relative to 100 parts by mass of the aromatic polyether. The content of the amorphous resin in the resin composition may be 300 parts by mass or less, 250 parts by mass or less, 200 parts by mass or less, 150 parts by mass or less, 100 parts by mass or less, 50 parts by mass or less, or 25 parts by mass, relative to 100 parts by mass of the aromatic polyether.

[0049] In one embodiment, the resin composition comprises 50% by weight or more, 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, 95% by weight or more, 97% by weight or more, 99% by weight or more, 99.5% by weight or more, or substantially 100% by weight of the aromatic polyether and the amorphous resin.

[0050] The method for producing the resin composition is not particularly limited. For example, the resin composition can be produced by the method described in the Examples.

[0051] 3. Composite Material A composite material according to one aspect of the present invention comprises the aromatic polyether or resin composition according to one aspect of the present invention and 0.01 to 500 parts by mass of reinforcing fibers per 100 parts by mass of the aromatic polyether or resin composition. The composite material according to this aspect exhibits excellent adhesion between the aromatic polyether or resin composition and the reinforcing fibers, resulting in excellent mechanical strength (e.g., tensile strength) as a composite material.

[0052] In one embodiment, the content of the reinforcing fibers in the composite material is, relative to 100 parts by mass of the aromatic polyether or resin composition, 0.01 parts by mass or more, 0.05 parts by mass or more, 0.1 parts by mass or more, 0.5 parts by mass or more, 1 part by mass or more, 5 parts by mass or more, 10 parts by mass or more, 15 parts by mass or more, 20 parts by mass or more, 30 parts by mass or more, or 40 parts by mass or more, and is 500 parts by mass or less, 400 parts by mass or less, 300 parts by mass or less, or 200 parts by mass or less.

[0053] In one embodiment, the content of the reinforcing fibers in the composite material is, relative to 100 parts by mass of the aromatic polyether or resin composition, 0.01 parts by mass to 500 parts by mass, 0.05 parts by mass to 500 parts by mass, 0.1 parts by mass to 500 parts by mass, 0.5 parts by mass to 400 parts by mass, 1 part by mass to 400 parts by mass, 5 parts by mass to 400 parts by mass, 10 parts by mass to 300 parts by mass, 15 parts by mass to 300 parts by mass, 20 parts by mass to 300 parts by mass, 30 parts by mass to 200 parts by mass, or 40 parts by mass to 200 parts by mass.

[0054] In one embodiment, the reinforcing fibers include one or more selected from the group consisting of carbon fibers, glass fibers, and aramid fibers. In one embodiment, 50 mass% or more, 60 mass% or more, 70 mass% or more, 80 mass% or more, 90 mass% or more, 95 mass% or more, 97 mass% or more, 99 mass% or more, 99.5 mass% or more, or substantially 100 mass% of the reinforcing fibers are one or more selected from the group consisting of carbon fibers, glass fibers, and aramid fibers.

[0055] In one embodiment, the carbon fiber comprises one or more selected from the group consisting of PAN-based carbon fiber, pitch-based carbon fiber, thermosetting carbon fiber, phenolic carbon fiber, vapor-grown carbon fiber, and recycled carbon fiber (RCF). In one embodiment, 50 mass% or more, 60 mass% or more, 70 mass% or more, 80 mass% or more, 90 mass% or more, 95 mass% or more, 97 mass% or more, 99 mass% or more, 99.5 mass% or more, or substantially 100 mass% of the carbon fiber is one or more selected from the group consisting of PAN-based carbon fiber, pitch-based carbon fiber, thermosetting carbon fiber, phenolic carbon fiber, vapor-grown carbon fiber, and recycled carbon fiber (RCF).

[0056] The types of glass fibers and aramid fibers are not particularly limited, and glass fibers of various compositions, such as E-glass, low dielectric glass, and silica glass, can be selected and used depending on the purpose and application.

[0057] In one embodiment, from the viewpoint of mechanical properties such as strength, elastic modulus, and impact resistance of a molded article formed using the composite material, the average fiber length of the reinforcing fibers in the composite material is 5 mm or more. The average fiber length is determined as the arithmetic mean of values ​​measured with a vernier caliper.

[0058] In one embodiment, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95%, at least 97%, at least 99%, at least 99.5%, or substantially 100% by weight of the composite material is the aromatic polyether or resin composition and reinforcing fibers.

[0059] The method for producing the composite material (composite method) is not particularly limited. For example, a method of melt-kneading an aromatic polyether or resin composition with reinforcing fibers, or a method of melting and impregnating an aggregate of reinforcing fibers with one or more forms of an aromatic polyether or resin composition selected from the group consisting of powder, film, and pellets, can be used. A composite material containing continuous reinforcing fibers with an average fiber length of 5 mm or more can be in one or more forms selected from the group consisting of a woven fabric, a nonwoven fabric, and a unidirectional material (also called a "UD material").

[0060] 4. Molded Article A molded article according to one aspect of the present invention includes the aromatic polyether or resin composition according to one aspect of the present invention. Therefore, it has excellent molding processability. A molded article according to another aspect of the present invention includes the composite material according to one aspect of the present invention. Therefore, it is possible to improve molding processability. Furthermore, since the interfacial shear strength between the aromatic polyether or resin composition and the reinforcing fibers in the composite material is excellent, it also has the effect of excellent mechanical strength (e.g., tensile strength).

[0061] The shape of the molded body according to one aspect and another aspect of the present invention is not particularly limited. In one embodiment, the molded body is an injection molded body, an extrusion molded body, or a compression molded body (also referred to as a "press molded body").

[0062] The uses of the aromatic polyethers, resin compositions, composite materials, and molded articles described above are not particularly limited, and can be widely applied to various applications requiring dimensional stability and strength. The aromatic polyethers, resin compositions, composite materials, and molded articles are suitable, for example, as metal replacement materials, particularly for applications requiring heat resistance, solvent resistance, and durability. More specifically, they can be used suitably for aerospace components, automotive components, sliding components such as gears and bearings, 3D printer filaments, and semiconductor manufacturing equipment components.

[0063] Examples of the present invention will be described below, but the present invention is not limited to these examples.

[0064] 1. Production of aromatic polyether (Example 1) 129.195 g (0.5145 mol) of 4,4'-dichlorobenzophenone (DCBP), 61.045 g (0.5544 mol) of hydroquinone (HQ), and 9.679 g (0.0563 mol) of 2,6-dichlorobenzonitrile (DCBN) were placed in a 2 L separable flask. Potassium carbonate (K ２ CO ３80.499 g (0.5821 mol) of HQ was added, and 480 g of diphenyl sulfone (DPS) (concentration: HQ × 2 [mol] / DPS [kg] = 2.31 mol / kg) was added as a solvent. A ribbon heater was wrapped around the top of the separable flask, and glass wool was wrapped around it to maintain the temperature. The mixture was heated and stirred using a mechanical stirrer under nitrogen (flow rate: 0.06 L / min). The ribbon heater was set to 150 °C and the mantle heater to 165 °C, and the stirring blade was manually rotated until the liquid temperature reached 150 °C. After the liquid temperature reached 150 °C, the mixture was stirred at 250 rpm using a mechanical stirrer and heated to 200 °C over 30 minutes. After the temperature increase, the temperature was maintained at 200 °C for 1 hour and then increased to 250 °C over 70 minutes. The temperature was maintained at 250 °C for 1 hour, and then increased to 300 °C over 150 minutes. After the temperature was raised, the temperature was maintained at 300°C for 144 minutes, and then 22.271 g (0.0887 mol) of DCBP was added to stop the reaction. During the addition, the nitrogen flow rate was temporarily increased to prevent oxygen and other contaminants from entering the system. After the addition, the temperature was maintained at 300°C for a predetermined time, and then the reaction was terminated and the mother liquor was taken out. The recovered product was pulverized and washed with acetone and water to obtain the target product (aromatic polyether). The structure was identified. １ It was confirmed by H-NMR under the following conditions and procedures that an aromatic polyether was produced by the following reaction.

[0065] [NMR measurement conditions] Magnet: Ascend 500 Spectrometer: AVANCE III HD Probe: 5 mm diameter TCI cryoprobe １ H resonance frequency: 500 MHz; Number of accumulations: 256; Waiting time: 10 seconds; Sample preparation: 0.6 mL of methanesulfonic acid was added to approximately 20 mg of sample and stirred at room temperature for 1 hour. 0.4 mL of deuterated dichloromethane was added to the sample to prepare the measurement sample. Chemical shift correction: The central peak of the three peaks of deuterated dichloromethane was set to 5.32 ppm.

[0066] [Procedure] The integral value A of the peak detected in the chemical shift range of 6.54 ppm to 6.74 ppm and the integral value B of the peak detected in the chemical shift range of 8.03 ppm to 8.17 ppm were obtained, and the copolymerization amount [mol %] (NMR) was calculated using the following formula. The results are shown in Table 1. Copolymerization amount [mol %] (NMR) = {(A / 2) / (A / 2 + B / 4)} × 100

[0067] A peak derived from the structural unit represented by formula (b) is observed in the integration range corresponding to integral value A. A peak derived from the structural unit represented by formula (a) is observed in the integration range corresponding to integral value B.

[0068] Examples 2 to 5 Aromatic polyethers were obtained in the same manner as in Example 1, except that the raw material equivalents including the molar ratio (DXBN / (DCBP+DXBN)) and the holding time (reaction time) at the maximum temperature (300°C in Examples 2 to 5, and 290°C in Example 4) were changed to the conditions shown in Table 1.

[0069] Example 6 Nitrogen gas was circulated through a 240 L reactor equipped with a stirrer, a thermometer, a nitrogen inlet tube, and a water collection container connected to a cooling tube. 132.47 kg of diphenyl sulfone (manufactured by Sino-High Corporation) was added stepwise, and the temperature was raised to 160°C. Once melting was confirmed, 27.30 kg (109 mol) of 4,4'-dichlorobenzophenone (manufactured by Sino-High Corporation), 8.40 kg (49 mol) of 2,6-dichlorobenzonitrile, 16.85 kg (153 mol) of hydroquinone, and 22.20 kg (160 mol) of potassium carbonate (AGC Corporation, fine powder) were added in that order. The reaction mixture was reacted under the following temperature control, and then 6.15 kg (25 mol) of 4,4'-dichlorobenzophenone was added as a reaction terminator. <Temperature Control> (1) At a stirring speed of 100 rpm, the temperature was increased from 160°C to 200°C over 90 minutes. (2) The temperature was maintained at 200°C for 60 minutes. (3) The temperature was increased from 200°C to 250°C over 80 minutes. (4) The temperature was maintained at 250°C for 60 minutes. (5) The temperature was increased from 250°C to 290°C over 100 minutes, and the stirring speed was changed to 64 rpm when 270°C was reached. (6) The temperature was maintained at 290°C for 116 minutes. (7) A reaction terminator was added, and the temperature was maintained at 100 rpm for 18 minutes. After the reaction was completed, the contents were removed onto a SUS tray, cooled to room temperature, and solidified. The product was coarsely pulverized and pulverized using a pin mill (160UPZ manufactured by Hosokawa Micron Corporation). The product was washed with acetone, an aqueous oxalic acid solution, and water, and then vacuum dried to obtain a powdery aromatic polyether. Comparative Example 1: Commercially available polyether ether ketone (abbreviated as PEEK) (151G) manufactured by Victrex was used. This PEEK is composed of structural units represented by formula (a) and does not contain structural units represented by formula (b). This PEEK is obtained by polymerizing difluorobenzophenone and hydroquinone as monomers, and does not contain dichlorobenzophenone.

[0070] Comparative Example 2 An aromatic polyether was obtained in the same manner as in Example 1, except that the use of DCBN was omitted and the raw material equivalent and the holding time (reaction time) at 300°C were changed to the conditions shown in Table 1.

[0071]

[0072] In Table 1, "copolymerization amount [mol %] (charge amount)" corresponds to the molar ratio (DXBN / (DCBP+DXBN)) and is a theoretical value calculated based on the amount of monomer charged. １ It means the percentage of the molar ratio ((b) / ((a)+(b))) of the structural unit represented by formula (b) to the total amount of the structural unit represented by formula (a) and the structural unit represented by formula (b), as measured by H-NMR. "Halogen-substituted monomer / OH[-]" is the molar ratio of the halogen-substituted monomer (total amount of DCBP and DXBN) to the OH monomer (HQ). "Base / OH[-]" is the molar ratio of the base (potassium carbonate) to the OH monomer (HQ). "Concentration [mol / kg]" is the value obtained by doubling the number of moles of the OH monomer (HQ) and dividing it by the mass [kg] of the solvent (diphenyl sulfone).

[0073] 2. Production of Alloy (Example 7) 93 parts by mass of the aromatic polyether obtained in Example 3 and 7 parts by mass of polyetherimide (1000P, manufactured by Saudi Basic Industries Corporation (SABIC)) were dry-blended to obtain a dry-blend raw material, which was melt-kneaded using a twin-screw extruder having a cylinder diameter of 11 mm at a screw rotation speed of 200 rpm and a set temperature of 350°C. The dry-blend raw material was fed from the base of the twin-screw extruder (upstream side of the screw) at a rate of 6 g per minute. The residence time in the twin-screw extruder was 3.5 minutes. The strands discharged from the twin-screw extruder were cooled in water and then pelletized using a pelletizer to obtain a pelletized aromatic polyether composition (alloy).

[0074] 3. Measurement and Evaluation Methods The following measurements and evaluations were carried out on the aromatic polyethers of Examples 1 to 6 and Comparative Examples 1 and 2, and the alloy of Example 7. (1) Measurement of Radical Amount The radical amount of the aromatic polyether or alloy (radical amount at 25°C measured using TEMPOL as the standard substance and benzene as the solvent for the standard substance) was measured by ESR (electron spin resonance) under the following conditions and procedures. [ESR Measurement Conditions] ESR Apparatus: JESFA200 Model, manufactured by JEOL Ltd. ESR Sample Tube Diameter: 5 mm Microwave Output: 0.5 mW Modulation Magnetic Field: 0.3 mT Time Constant: 0.03 seconds Magnetic Field Range: 328-344 mT Measurement Time: 60 seconds Mn Intensity: 650 Measurement Temperature: 25°C [Procedure] TEMPOL (4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl) was dissolved in benzene to a concentration of 5 μM, and 400 μL was added to an ESR sample tube. ESR was measured under the above measurement conditions. The integral of the resulting TEMPOL-derived peak was divided by the integral of the Mn peak for normalization (integral value A). The measurement sample was then weighed (weighed value B) and loaded into an ESR sample tube. ESR was measured under the above measurement conditions. The integral value of the peak derived from the obtained sample was divided by the integral value of the Mn peak and normalized (integral value C). Using the obtained values ​​of A, B, and C, the amount of radicals per unit weight of the sample was calculated according to the following formula: Amount of radicals per unit weight of sample [spin / g] = (5 × 10 －６ x400 x 10 －６ x 6.02 x 10 ２３ × C) / (A × B)

[0075] (2) Measurement of Glass Transition Temperature (Tg), Melting Point (Tm), Heat of Fusion (ΔH), and Crystallinity A differential scanning calorimeter (DSC) (PerkinElmar DSC 8500) was used. The instrument was calibrated and inspected using standard samples of indium and lead. A 5 mg test piece of press-molded aromatic polyether or alloy was placed in an aluminum pan, heated to 420°C at a rate of 20°C / min, and held for 1 minute. The glass transition temperature (Tg) was determined as the temperature at the point where a line equidistant along the vertical axis from the line extending the baselines on the low and high specific heat capacity sides of the specific heat capacity change intersects with the curve of the stepwise change in glass transition. The melting point (Tm) was determined as the temperature at the apex of the endothermic peak due to crystalline melting. The heat of fusion (ΔH) was then divided by 130 J / g to derive the crystallinity (%). For the aromatic polyether of Example 6, no test specimens were prepared, and the powder was used for measurement. The "test specimens" were obtained by the following method. The aromatic polyether or alloy was filled into a mold and pressed at a temperature of 350°C using a vacuum press (IMC-6215, manufactured by Imoto Machinery Works). After pressing, the mixture was annealed at 180°C for 1 hour while maintaining pressure, yielding a flat plate with a thickness of 0.5 mm. This flat plate was punched out using a punching machine to form a No. 6 dumbbell test specimen (JIS K-6251).

[0076] (3) Measurement of Complex Viscosity The complex viscosity of the aromatic polyethers and alloys was measured using a viscoelasticity measuring device under the following conditions and procedures. Note that for the aromatic polyethers of Examples 5 and 6, the measurement was performed under partially changed measurement conditions as described below.

[0077] [Measurement conditions] Viscoelasticity measuring device: MCR302 (manufactured by Anton Paar) Jig: SHAFT FOR DISPOSABLE MEASUREMENT SYSTEM D-CP / PP25 Disposable dish: Φ41 mm Disposable parallel plate: Φ25 mm Temperature: 360°C Preheating time: 3 minutes Gap: 0.8 mm Time: 300 min Shear strain: 1% Angular frequency: 6.28 rad / s

[0078] The changes in the measurement conditions in Examples 5 and 6 are as follows: [Measurement conditions] Temperature: 350°C Time: 300 seconds Angular frequency: 2.76 rad / s

[0079] [Procedure] A disk-shaped aromatic polyether or alloy was placed in a disposable dish and measured under the conditions described above. For the measurement, a sample was sandwiched between a disposable dish and a disposable plate with a gap of 0.8 mm, preheated, and then trimmed to a diameter of 25 mm. The complex viscosity in Examples 1 to 4 is the value at 5 min in the molten state. The complex viscosity in Examples 5 and 6 is the value at 1 min in the molten state. The "discs" were obtained by the following method. The aromatic polyether or alloy was filled into a mold and pressed at a temperature of 350°C using a vacuum press (IMC-6215, manufactured by Imoto Machinery Co., Ltd.). After pressing, the sample was quenched at 25°C to form a disk with a diameter of 25 mm and a thickness of 1.0 mm.

[0080] The results are shown in Tables 2 and 3.

[0081]

[0082] As is clear from Table 2, the aromatic polyether of the present invention can lower the melting point (Tm) without lowering the glass transition temperature (Tg). It can also be seen that the Tg is maintained for the aromatic polyether of Example 5. For the aromatic polyether of Example 5, no melting point (Tm) was detected under the above measurement conditions. From the above results, it can be seen that the polyether of the present invention can achieve a lower processing temperature while maintaining heat resistance. Furthermore, the aromatic polyether of the present invention can also lower the crystallinity, thereby suppressing shrinkage during the cooling process during molding and preventing the formation of cavities inside the molded article. As a result, molding processability can be improved. Furthermore, the aromatic polyether of the present invention can achieve these effects while maintaining a high radical concentration, thereby also achieving adhesion to reinforcing fibers.

[0083] In Table 3, it can be seen that the resin composition (alloy) of the present invention, compared to Example 3 consisting only of the corresponding aromatic polyether, contains polyetherimide, resulting in a slight increase in glass transition temperature (Tg) (in other words, without lowering the glass transition temperature (Tg)), a unchanged melting point (Tm), and a resulting decrease in Δ(Tm-Tg). From these results, it can be seen that the resin composition (alloy) of the present invention can achieve lower processing temperatures while maintaining heat resistance. Furthermore, the resin composition (alloy) of the present invention can also reduce the degree of crystallinity, thereby suppressing shrinkage during the cooling process during molding and preventing the formation of voids inside the molded product. As a result, molding processability can be improved. Furthermore, the resin composition (alloy) of the present invention can achieve these effects while maintaining a high radical concentration, thereby achieving adhesion to reinforcing fibers.

[0084] 4. Production of Composite Material (Example 8) 100 parts by mass of the aromatic polyether obtained in Example 6 and 43 parts by mass of an inorganic filler ("T-786H" manufactured by Nippon Electric Glass Co., Ltd., chopped glass fiber, average fiber length 3 mm, filament diameter 11 μm) were melt-kneaded at a set temperature of 350° C. using a twin-screw kneader ("Process-11" manufactured by Termo Fisher Scientific, cylinder volume 20 cc) having a cylinder diameter of 11 mm, to obtain a composite material (pellets).

[0085] (Example 9) A composite material (pellet) was obtained in the same manner as in Example 8, except that the inorganic filler in Example 8 was changed to discontinuous carbon fiber ("TR06U" manufactured by Mitsubishi Engineering-Plastics Corporation, chopped carbon fiber, average fiber length 6 mm, filament diameter 7 μm).

[0086] 5. Evaluation of Composite Material (1) Radical Amount of Composite Material In the measurement of the "radical amount of aromatic polyether" described above, the radical amount of the composite material was measured by using a composite material instead of the aromatic polyether as the measurement sample. Note that, for Example 9, measurement of the radical amount of the composite material was omitted.

[0087] (2) Tensile Strength and Breaking Strain The obtained composite material was dried at 140°C for 2 hours or more and injection molded using a small molding machine (MiniJet-Pro, manufactured by Haake Co., Ltd.) at a cylinder temperature of 370°C and a mold temperature of 180°C to prepare test specimens specified in ISO527-2-1BA. The obtained test specimens were subjected to a tensile test at a test speed of 1 mm / min and a chuck distance of 50 mm to measure the tensile strength and breaking strain (tensile elongation). The results are shown in Table 4.

[0088]

[0089] From Table 4, it can be seen that the composite materials of Examples 8 and 9 have excellent adhesion to reinforcing fibers and are expected to have improved moldability, based on their tensile strength values. Therefore, they can be widely used in a variety of applications where dimensional stability and strength are required.

[0090] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will readily be able to make numerous modifications to these exemplary embodiments and / or examples without substantially departing from the novel teachings and advantages of the present invention. Accordingly, these numerous modifications are within the scope of the present invention. The contents of all documents cited in this specification and of the applications from which this application claims priority under the Paris Convention are incorporated by reference in their entirety.

Claims

1. Contains a structural unit represented by the following formula (a) and a structural unit represented by the following formula (b), and has a radical amount of 6.5 x 10 at 25°C, measured using TEMPOL as the standard substance and benzene as the solvent for the standard substance. １５ ~9.0 x 10 １７ (spin / g) of an aromatic polyether.

2. The aromatic polyether according to claim 1, which contains a structural unit represented by the following formula (b') as the structural unit represented by the formula (b):

3. The aromatic polyether according to claim 1 or 2, having a glass transition temperature (Tg) of 140°C or higher.

4. The aromatic polyether according to any one of claims 1 to 3, having a melting point (Tm) of 330°C or lower.

5. The aromatic polyether according to any one of claims 1 to 4, wherein the difference between the melting point (Tm) and the glass transition temperature (Tg) (Δ(Tm-Tg)) is 185°C or less.

6. The aromatic polyether according to any one of claims 1 to 5, having a crystallinity (%) of 33% or less.

7. The aromatic polyether according to any one of claims 1 to 6, having a crystallinity (%) of 5% or more and 30% or less.

8. The aromatic polyether according to any one of claims 1 to 7, which is a copolymer of 4,4'-dichlorobenzophenone (DCBP), dihalogenobenzonitrile (DXBN) and hydroquinone (HQ).

9. The aromatic polyether of claim 8, wherein the dihalogenobenzonitrile comprises 2,6-dichlorobenzonitrile (DCBN).

10. The aromatic polyether according to claim 8 or 9, wherein the molar ratio of the dihalogenobenzonitrile (DXBN) to the total amount of the 4,4'-dichlorobenzophenone (DCBP) and the dihalogenobenzonitrile (DXBN) (DXBN / (DCBP+DXBN)) is 5 to 40 mol %.

11. The aromatic polyether according to any one of claims 1 to 10, wherein 50% by mass or more of the aromatic polyether is the structural unit represented by formula (a) and the structural unit represented by formula (b).

12. A composition comprising an aromatic polyether according to any one of claims 1 to 11 and an amorphous resin, or an aromatic polyether comprising a structural unit represented by the following formula (a) and a structural unit represented by the following formula (b), and an amorphous resin, wherein the amount of radicals at 25°C measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance is 6.5 x 10 １５ ~9.0 x 10 １７ (spin / g).

13. A composite material comprising the aromatic polyether according to any one of claims 1 to 11 or the resin composition according to claim 12, and 0.01 to 500 parts by mass of reinforcing fibers per 100 parts by mass of the aromatic polyether or resin composition.

14. The composite material of claim 13, wherein the reinforcing fibers comprise one or more selected from the group consisting of carbon fibers, glass fibers, and aramid fibers.

15. A method for producing the aromatic polyether according to any one of claims 1 to 11, comprising reacting 4,4'-dichlorobenzophenone (DCBP), a dihalogenobenzonitrile (DXBN), and hydroquinone (HQ).

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