Resin composition, composite material, molded article, and method for producing resin composition

Abstract

This resin composition contains: an aromatic polyether (A) having a radical amount at 25°C of 6.5×1015-9.0×1017 spin / g as measured with a standard substance of TEMPOL and a solvent for the standard substance of benzene; and an inorganic phosphate metal salt (B) in an amount of 0.01-5.0 parts by mass relative to 100 parts by mass of the aromatic polyether (A).

Description

Resin composition, composite material, molded article, and method for producing resin composition

[0001] The present invention relates to a resin composition, a composite material, a molded article, and a method for producing a resin composition. Specifically, the present invention relates to a resin composition, a composite material, a molded article, and a method for producing a resin composition, which can produce a molded article having excellent mechanical properties and excellent thermal stability.

[0002] Aromatic polyethers have excellent heat resistance and mechanical strength, and these characteristics have led to their use as metal replacement materials. In recent years, their applications have expanded to include automobiles, aircraft, and the medical field. Patent Document 1 describes a resin composition containing nanodiamond particles and a thermoplastic resin with a melting point of 280°C or higher or a glass transition temperature of 220°C or higher, with the aim of suppressing radical crosslinking reactions in thermoplastic resins such as aromatic polyether ketone (improving thermal stability). Patent Document 2 attempts to improve thermal stability by incorporating 0.10 to 0.35% by weight of sodium dihydrogen orthophosphate and 0.08 to 0.25% by weight of disodium hydrogen phosphate into polyether ether ketone (PEEK).

[0003] WO 2017 / 38333 UK Patent Application Publication No. 2536387

[0004] However, it was found that there is room for further improvement in the thermal stability of the resin composition of Patent Document 1.

[0005] One object of the present invention is to provide a resin composition, a composite material, and a molded article that can be produced from a resin composition having excellent mechanical properties and excellent thermal stability, as well as a method for producing the resin composition.

[0006] As a result of extensive research, the present inventors have found that blending an aromatic polyether having a specific radical content with an inorganic metal phosphate not only improves thermal stability but also improves the mechanical properties of molded articles, thereby completing the present invention. Furthermore, as a result of extensive research, the present inventors have found that a resin composition containing an aromatic polyether, phosphorus atoms, and sodium atoms and having a specific radical content has excellent thermal stability and can improve the mechanical properties of molded articles, thereby completing the present invention.

[0007] According to the present invention, the following resin composition can be provided: 1. The amount of radicals measured at 25°C 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 A resin composition comprising an aromatic polyether (A) having a molecular weight of 1.5 spin / g and 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) relative to 100 parts by mass of the aromatic polyether (A). 2. The resin composition according to item 1 above, wherein the aromatic polyether (A) is polyarylene ether ketone. 3. The resin composition according to item 1 or 2 above, wherein the aromatic polyether (A) comprises one or more members selected from the group consisting of polyether ether ketone (PEEK) and polyether ketone (PEK). 4. The resin composition according to any one of items 1 to 3 above, wherein the inorganic metal phosphate (B) comprises an alkali metal. 5. The resin composition according to any one of items 1 to 4 above, wherein the inorganic metal phosphate (B) comprises two or more metal species. 6. A resin composition comprising an aromatic polyether, a phosphorus atom (P), and a sodium atom (Na), wherein the radical amount at 25°C is 6.5 x 10, measured using TEMPOL as a standard substance and benzene as a solvent for the standard substance. １５ ~9.0 x 10 １７spin / g. 7. The resin composition according to any one of 1 to 6 above, wherein the content of sodium atoms (Na) is 100 ppm or more. 8. The resin composition according to any one of 1 to 7 above, wherein the content of phosphorus atoms (P) is 100 ppm or more. 9. The resin composition according to any one of 1 to 8 above, wherein the complex viscosity of the resin composition measured using a viscoelasticity measuring device at a set temperature of 420°C satisfies the following formula (R1): Complex viscosity after 60 minutes of measurement / Complex viscosity after 1 minute of measurement≦2.0 (R1) 10. The resin composition according to any one of 1 to 9 above, wherein the loss tangent (tan δ) after 60 minutes of measurement using a viscoelasticity measuring device at a set temperature of 420°C is 0.5 or more. 11. The resin composition according to any one of 1 to 10 above, wherein the complex viscosity and loss tangent (tan δ) after 60 minutes of measurement using a viscoelasticity measuring device at a set temperature of 420°C satisfy the following formula (R2): Loss tangent (tan δ) × complex viscosity ≦ 7500 (R2) 12. A composite material comprising the resin composition according to any one of items 1 to 11 above, and 0.01 to 500 parts by mass of reinforcing fiber (C) relative to 100 parts by mass of the resin composition. 13. The composite material according to item 12 above, wherein the reinforcing fiber (C) comprises one or more types selected from the group consisting of carbon fiber, glass fiber, and aramid fiber. 14. The composite material according to item 12 or 13 above, wherein the reinforcing fiber (C) in the composite material has an average fiber length of 5 mm or more. 15. A molded article comprising the resin composition according to any one of items 1 to 11 above. 16. A molded article comprising the composite material according to any one of items 12 to 14 above. 17. The molded article according to item 15 or 16 above, wherein the molded article is an injection-molded article. 18. The molded article according to item 15 or 16 above, wherein the molded article is an extrusion-molded article. 19. The molded article according to item 15 or 16 above, wherein the molded article is a compression-molded article.20. A method for producing a resin composition, comprising: a reaction step of reacting 4,4'-dichlorobenzophenone and hydroquinone in the presence of a reaction solvent to obtain an aromatic polyether, a washing step of washing the aromatic polyether obtained in the reaction step, an aromatic polyether drying step of drying the aromatic polyether obtained in the washing step, and a kneading step of melting and kneading 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) per 100 parts by mass of the aromatic polyether obtained in the aromatic polyether drying step to obtain a kneaded mixture. 21. A method for producing a resin composition, comprising: a reaction step of reacting 4,4'-dichlorobenzophenone and hydroquinone in the presence of a reaction solvent to obtain an aromatic polyether, a washing step of washing the aromatic polyether obtained in the reaction step, a mixing step of mixing 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) per 100 parts by mass of the aromatic polyether obtained in the washing step in the presence of a solvent to obtain a mixture, and a mixture drying step of drying the mixture obtained in the mixing step.

[0008] According to the present invention, it is possible to provide a resin composition, a composite material, a molded article, and a method for producing a resin composition, which are capable of producing a molded article having excellent mechanical properties and excellent thermal stability.

[0009] The resin composition, composite material, and molded article of the present invention, as well as the method for producing the resin composition, 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 mutually exclusive embodiments can be combined, and an embodiment combining two or more embodiments is also an embodiment of the aspects of the present invention.

[0010] 1. Resin Composition [First Resin Composition] The resin composition according to one aspect of the present invention (hereinafter also referred to as "first resin composition") 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 １７and 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) relative to 100 parts by mass of the aromatic polyether (A).

[0011] The resin composition according to this embodiment can exhibit excellent interfacial adhesive strength to reinforcing fibers such as inorganic fillers, and also has excellent thermal stability. Furthermore, by using the resin composition in the production of composite materials and molded articles, composite materials and molded articles with excellent mechanical properties (e.g., tensile modulus and elongation) can be produced. The mechanical properties of the composite materials and molded articles can be measured according to the methods described in the examples.

[0012] The reason why such an effect is obtained is not entirely clear, but the amount of radicals is 6.5 × 10 １５ ~9.0 x 10 １７ It is presumed that the large amount of spin / g causes interactions with the reinforcing fibers and the formation of chemical bonds. On the other hand, the amount of radicals was 6.5 × 10 １５ ~9.0 x 10 １７ It is believed that the aromatic polyether (A) alone, at a high concentration of 10 ...

[0013] In one embodiment, the complex viscosity of the first resin composition measured using a viscoelasticity measuring device at a set temperature of 420°C satisfies the following formula (R1): complex viscosity after 60 minutes of measurement / complex viscosity after 1 minute of measurement≦2.0 (R1)

[0014] In other words, in one embodiment, when the complex viscosity is measured at a set temperature of 420°C using a viscoelasticity measuring device, the ratio of the complex viscosity after 60 minutes of measurement to the complex viscosity after 1 minute of measurement (complex viscosity after 60 minutes of measurement / complex viscosity after 1 minute of measurement) may be 2.0 or less, 1.9 or less, 1.8 or less, or 1.7 or less. When the complex viscosity satisfies the above condition, the effect of excellent thermal stability is easily obtained when the resin composition is melted.

[0015] The complex viscosity of the resin composition is a value measured by the method described in the examples.

[0016] In one embodiment, the loss tangent (tan δ) after 60 minutes of measurement at a set temperature of 420° C. using a viscoelasticity measuring device is 0.50 or more, or may be 0.60 or more, 0.70 or more, 0.80 or more, or 0.90 or more. The upper limit is not particularly limited, and may be, for example, 15.0 or less, 10.0 or less, or 5.0 or less.

[0017] When the loss tangent (tan δ) satisfies the above condition, the resin is more likely to be oriented during molding of the resin composition, and the mechanical properties of the resulting molded article can be expected to be improved.

[0018] The loss tangent (tan δ) of the resin composition is a value measured by the method described in the examples.

[0019] In one embodiment, the complex viscosity and loss tangent (tan δ) measured using a viscoelasticity measuring device at a set temperature of 420°C satisfy the following formula (R2): Loss tangent (tan δ) × complex viscosity≦7500 (R2)

[0020] In one embodiment, the product of the complex viscosity and the loss tangent (tan δ) measured using a viscoelasticity measuring device at a set temperature of 420°C may be 7500 or less, 7200 or less, 7000 or less, 6800 or less, 6500 or less, 6200 or less, or 6000 or less.

[0021] In the resin composition according to one aspect of the present invention, when the complex viscosity and loss tangent (tan δ) satisfy the above conditions, the viscosity of the resin when molten tends to be suitable for molding processes such as extrusion molding, film molding, etc. As a result, the suitability of the resin composition for molding processes, i.e., moldability, can be expected to be improved.

[0022] (Aromatic Polyether (A)) The first resin composition according to one aspect of the present invention 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 The aromatic polyether (A) has a molecular weight of 1.0001 to 1.0001.

[0023] The aromatic polyether (A) can exhibit excellent interfacial adhesive strength to reinforcing fibers such as inorganic fillers and also has excellent toughness. Furthermore, by using the aromatic polyether (A) in the production of composite materials and molded articles, composite materials and molded articles having excellent mechanical properties can be produced.

[0024] The reason why such an effect is obtained is not entirely clear, but the amount of aromatic polyether radicals is 6.5 × 10 １５ Since the amount of the aromatic polyether is as high as 1 / spin / g or more, it is presumed that the aromatic polyether interacts with the reinforcing fibers or forms chemical bonds, etc. The toughness of the aromatic polyether can be evaluated, for example, by the breaking strain (tensile elongation) measured by the method described in the Examples.

[0025] The radical amount of the aromatic polyether is a value measured by the method described in the examples.

[0026] In this specification, unless otherwise specified, the "radical amount" of an aromatic polyether means the "radical amount per unit mass (unit: spin / g)" of the aromatic polyether. In this specification, unless otherwise specified, "TEMPOL" means "4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl."

[0027] In one embodiment, the radical amount of the aromatic polyether (A) is 6.5×10 １５ spin / g or more, 7.0×10１５ spin / g or more, 8.0×10 １５ spin / g or more, 8.9×10 １５ spin / g or more, 1.0×10 １６ spin / g or more, 2.0×10 １６ spin / g or more, 3.0×10 １６ spin / g or more, 4.0×10 １６ spin / g or more, or 5.0 x 10 １６ spin / g or more, and １７ spin / g or less, 5.0×10 １７ spin / g or less, 4.0×10 １７ spin / g, 3.7×10 １７ spin / g or less, or 1.0 x 10 １７ The amount of radicals in the aromatic polyether (A) is 6.5×10 １５ When the aromatic polyether (A) has a radical content of 9.0×10 or more, the above-mentioned composite effect and the like are easily obtained, and the interfacial shear strength with the reinforcing fiber is easily obtained. １７ When the viscosity is less than or equal to spin / g, thermal stability is easily obtained and sufficient mechanical properties are easily exhibited as a molded article.

[0028] The amount of radicals in the aromatic polyether can be increased to the above-mentioned range, for example, by using a monomer containing a chlorine atom as a reactive group (e.g., 4,4′-dichlorobenzophenone) as a monomer when synthesizing (polymerizing) the aromatic polyether.

[0029] In one embodiment, the aromatic polyether (A) is a polyarylene ether ketone. In one embodiment, the aromatic polyether (A) comprises one or more selected from the group consisting of polyether ether ketone (PEEK), polyether ketone ketone (PEKK), and polyether ketone (PEK). In one embodiment, the aromatic polyether (A) comprises one or more selected from the group consisting of polyether ether ketone (PEEK) and polyether ketone (PEK). From the viewpoints of moldability, mechanical properties, and environmental resistance, it is preferable that the aromatic polyether (A) comprises polyether ether ketone (PEEK).

[0030] 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 (A) is one or more selected from the group consisting of polyetheretherketone (PEEK), polyetherketoneketone (PEKK), and polyetherketone (PEK). 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 (A) is polyetheretherketone (PEEK).

[0031] In one embodiment, the aromatic polyether (A) contains a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2).

[0032] In one embodiment, the aromatic polyether (A) contains a structural unit represented by the following formula (3):

[0033] The structural unit represented by formula (3) is a bond between the structural unit represented by formula (1) and the structural unit represented by formula (2).

[0034] In one embodiment, the aromatic polyether (A) does not contain any other structure than the structural units represented by formula (1) and formula (2).

[0035] In one embodiment, the aromatic polyether (A) contains a structure other than the structural units represented by formula (1) and formula (2) within a range that does not impair the effects of the present invention.

[0036] In one embodiment, the aromatic polyether comprises a structural unit represented by the following formula (a) and one or more structural units selected from the group consisting of structures represented by the following formulas (b) and (c):

[0037] The structural unit represented by formula (a) corresponds to the structural unit represented by formula (3) above, and is a bond between the structural unit represented by formula (1) and the structural unit represented by formula (2).

[0038] In one embodiment, the aromatic polyether can also be said to be a copolymer of a structural unit represented by formula (a) and one or more structural units selected from the group consisting of formulas (b) and (c).

[0039] In one embodiment, the copolymer is a random copolymer, an alternating copolymer, or a block copolymer, preferably a random copolymer.

[0040] In one embodiment, in the aromatic polyether, the substitution position (bonding position) of the phenyl group in the structural unit represented by formula (b) can be any position on the benzene ring constituting the main chain shown on the far right in formula (b) (the phenyl group is introduced so as to substitute any of the four hydrogen atoms on the benzene ring).

[0041] When two or more structural units represented by formula (b) are adjacent in an aromatic polyether, the aromatic polyether may contain one or more structures selected from the group consisting of a structure represented by the following (b1), a structure represented by the following (b2), and a structure represented by the following (b3):

[0042] In each of the structures represented by the formulas (b1) to (b3), the substitution positions of the phenyl groups in the two structural units represented by the formula (b) that form the structure are different from each other. The effects of the present invention are well exhibited in any of the structures.

[0043] Here, the case where two or more structural units represented by formula (b) are adjacent to each other has been described, but even when two or more structural units represented by formula (b) are arranged via other structural units (for example, structural units represented by formula (a)), the substitution positions of the phenyl groups in these structural units represented by formula (b) may be the same or different. In either case, the effects of the present invention are well exhibited.

[0044] In one embodiment, the aromatic polyether comprises 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 structural unit represented by formula (a) and the structural unit represented by formula (b). Note that "substantially 100% by mass" may contain inevitable impurities.

[0045] In one embodiment, the aromatic polyether has a molar ratio 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) of 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, or 40 mol% or less.

[0046] In one embodiment, the aromatic polyether comprises 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 structural unit represented by formula (a) and the structural unit represented by formula (c). Note that "substantially 100% by mass" may contain inevitable impurities.

[0047] In one embodiment, the aromatic polyether has a molar ratio of the structural unit represented by formula (c) to the total amount of the structural unit represented by formula (a) and the structural unit represented by formula (c) of 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 99 mol% or less, 90 mol% or less, 80 mol% or less, 70 mol% or less, 60 mol% or less, 50 mol% or less, or 40 mol% or less.

[0048] The structural unit represented by formula (a) and one or more structural units selected from the group consisting of structures represented by formulas (b) and (c) can be copolymerized within a range that does not impair the effects of the present invention.

[0049] In one embodiment, the aromatic polyether includes a structural unit represented by the following formula (a) and a structural unit represented by the following formula (d), 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).

[0050]

[0051] In one embodiment, the copolymer is a random copolymer, an alternating copolymer, or a block copolymer, preferably a random copolymer.

[0052] In one embodiment, the structural unit represented by formula (d) is a structural unit represented by formula (c).

[0053] The structural unit represented by formula (a) and the structural unit represented by formula (d) can be copolymerized to the extent that the effects of the present invention are not impaired.

[0054] In one embodiment, the aromatic polyether comprises 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. Note that "substantially 100% by mass" may contain inevitable impurities.

[0055] In one embodiment, the aromatic polyether has a molar ratio of the structural unit represented by formula (d) to the total amount of the structural unit represented by formula (a) and the structural unit represented by formula (d) of 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 99 mol% or less, 90 mol% or less, 80 mol% or less, 70 mol% or less, 60 mol% or less, 50 mol% or less, or 40 mol% or less.

[0056] 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 (A) is the structural unit represented by formula (1) and the structural unit represented by formula (2), or the structural unit represented by formula (3). Note that when it is "substantially 100% by mass", it may contain inevitable impurities.

[0057] In one embodiment, in the aromatic polyether (A), the molar ratio of the structural unit represented by formula (1) to the structural unit represented by formula (2) (structural unit represented by formula (1) : structural unit represented by formula (2)) is 47.5:52.5 to 52.5:47.5, 48.0:52.0 to 52.0:48.0, 48.5:51.5 to 51.5:48.5, 49.0:51.0 to 51.0:49.0, or 49.5:50.5 to 50.5:49.5. The number of moles of the structural unit represented by formula (1) may be greater than, smaller than, or the same as the number of moles of the structural unit represented by formula (2).

[0058] The terminal structure of the main chain of the aromatic polyether (A) is not particularly limited. In one embodiment, a structural unit represented by formula (1) is disposed at one or more ends of the main chain of the aromatic polyether (A). In this case, the terminal structure bonded to the structural unit may be a halogen atom. The halogen atom may be, for example, a chlorine atom (Cl) or a fluorine atom (F). In one embodiment, a structural unit represented by formula (2) is disposed at one or more ends of the main chain of the aromatic polyether (A). In this case, the terminal structure bonded to the structural unit may be, for example, a hydrogen atom (H) or the like (when the terminal structure is a hydrogen atom (H), a hydroxyl group is formed together with the oxygen atom (O) in the structural unit). The terminal structure of the aromatic polyether (A) may be, for example, a structure in which the above-mentioned halogen atom or hydroxyl group is replaced with a hydrogen atom (H). The terminal structure may have a structure other than those exemplified above. For example, the terminal structure may have a structure derived from a reaction terminator.

[0059] In one embodiment, the aromatic polyether (A) has a melt flow rate (MFR) of 1500 g / 10 min or less, 1000 g / 10 min or less, 500 g / 10 min or less, 300 g / 10 min or less, 200 g / 10 min or less, 100 g / 10 min or less, 80 g / 10 min or less, 60 g / 10 min or less, or 50 g / 10 min or less, and 0.0001 g / 10 min or more, 0.0005 g / 10 min or more, 0.001 g / 10 min or more, 0.005 g / 10 min or more, 0.01 g / 10 min or more, 0.05 g / 10 min or more, or 0.1 g / 10 min or more. The melt flow rate of the aromatic polyether (A) is, for example, 0.001 to 500 g / 10 min, preferably 0.01 to 100 g / 10 min from the viewpoint of mechanical properties, and more preferably 0.05 to 50 g / 10 min from the viewpoint of moldability. The melt flow rate of the aromatic polyether (A) can be measured by the method described in the Examples.

[0060] In one embodiment, the aromatic polyether (A) has a potassium atom (K) content of 0 ppm or more and 200 ppm or less. The potassium atom content can be measured by the method described in the examples.

[0061] In this specification, the phrase "the content of potassium atoms (K) is 0 ppm or more and 200 ppm or less" means that the aromatic polyether (A) may contain potassium atoms as free components.

[0062] The potassium atom may be a free component as a simple substance, or may be a free component as a compound with other atoms, an ion, etc. The potassium atom content is the ratio to the total amount of the resin composition and the free component.

[0063] In one embodiment, the lower limit of the potassium atom content in the aromatic polyether (A) may be, for example, 0.01 ppm, 0.1 ppm, 1.0 ppm, 2.0 ppm, 5.0 ppm, or 10.0 ppm.

[0064] In one embodiment, the upper limit of the potassium atom content in the aromatic polyether (A) may be, for example, 200 ppm, 150 ppm, 120 ppm, 100 ppm, 80 ppm, 60 ppm, or 50 ppm.

[0065] The potassium atom may be, but is not limited to, a potassium atom derived from a base used in synthesizing the aromatic polyether.

[0066] (Inorganic Metal Phosphate (B)) In this specification, inorganic metal phosphate refers to a metal salt of a phosphorus-containing acid, which is an inorganic compound.

[0067] Phosphorus-containing acids include, but are not limited to, phosphoric acid, pyrophosphoric acid, polytriphosphoric acid, tetrapolyphosphoric acid, phosphorous acid, hypophosphorous acid, phosphonic acid, phosphinic acid, and the like.

[0068] Metal salts include, but are not limited to, alkali metals, alkaline earth metals, earth metals, etc. Alkali metals include, but are not limited to, lithium, sodium, etc. Alkaline earth metals include, but are not limited to, magnesium, calcium, strontium, etc. Earth metals include, but are not limited to, aluminum, gallium, indium, etc.

[0069] Specific examples of the inorganic metal phosphate (B) include LiPO ４ , Na ２ HPO ４ , NaH ２ P.O. ４ , NaH ２ P.O. ２ , Na ３ P.O. ４ , Na ４ P ２ O ７ , Na ２ H ２ P ２ O ７ , Na ５ P ３ O １０ , Na ６ P ４ O １３ , K. ２ P ２ O ７ , CaHPO ４ , Ca(H ２ P.O. ４ ) ２ , CaHPO ４ , Ca ３ (P.O. ４ ) ２ , K.H. ２ P.O. ４ , K. ２ HPO ４ , K. ３ P.O. ４ , K. ４ P ２ O ７ , K. ５ P ３ O １０ , Mg ２ P ２ O ７ , Mg(H ２ P.O.４ ), MgHPO ４ , Mg ３ (P.O. ４ ) ２ , Mg(PO ３ ) ２ , Al(H ２ P.O. ４ ), AlPO ４ , Al(PO ３ ) ３ , and hydrates thereof, but are not limited to these. These inorganic metal phosphates (B) may be used alone or in combination of two or more. Among these, from the viewpoints of toughness, heat resistance, and moldability, it is preferable that the inorganic metal phosphate (B) contains an alkali metal. The inorganic metal phosphate (B) may contain only one metal species, or may contain two or more metal species.

[0070] The content of the inorganic metal phosphate (B) in the resin composition is 0.01 parts by mass or more, 0.02 parts by mass or more, 0.05 parts by mass or more, 0.10 parts by mass or more, 0.20 parts by mass or more, or 0.50 parts by mass or more, and 5.0 parts by mass or less, 3.0 parts by mass or less, 2.0 parts by mass or less, or 1.0 part by mass or less, relative to 100 parts by mass of the aromatic polyether (A). When the content of the inorganic metal phosphate (B) is 0.01 parts by mass or more, the effect of excellent thermal stability is likely to be obtained. Furthermore, when the content of the inorganic metal phosphate (B) is 5.0 parts by mass or less, the effect of excellent mechanical properties of the molded body is likely to be obtained.

[0071] The resin composition may contain other components in addition to the aromatic polyether (A) and the inorganic metal phosphate (B) as long as the effects of the present invention are not impaired. Examples of the other components include resins other than the aromatic polyether (A). Examples of the other resins include amorphous resins and fluororesins. One type of the other component may be used alone, or two or more types may be used in combination.

[0072] The amorphous resin may be an amorphous thermoplastic resin having a glass transition temperature of 180°C or higher. A glass transition temperature of 180°C or higher can impart an excellent effect of high heat resistance. Specific examples include polyetherimide (PEI), polyethersulfone (PES), polyphenylene ether (PPE), polysulfone (PSU), and polyimide (PI). Among these, PEI is preferred from the viewpoints of toughness, heat resistance, and moldability.

[0073] An example of the fluororesin is polytetrafluoroethylene.

[0074] 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 resin composition is the aromatic polyether (A) and the inorganic metal phosphate (B). 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 resin composition is the aromatic polyether (A), the inorganic metal phosphate (B), and the amorphous resin. In addition, in the case of "substantially 100% by mass", unavoidable impurities may be included.

[0075] In one embodiment, the first resin composition contains phosphorus atoms (P) and sodium atoms (Na). The presence of phosphorus atoms (P) and sodium atoms (Na) in the resin composition can be confirmed by inductively coupled plasma atomic emission spectroscopy described in the examples.

[0076] In one embodiment, the content of phosphorus atoms (P) in the first resin composition is 100 ppm or more, 150 ppm or more, 200 ppm or more, 400 ppm or more, 600 ppm or more, 800 ppm or more, or 1000 ppm or more. When the content of phosphorus atoms (P) in the first resin composition is in the above range, the effect of excellent thermal stability is likely to be obtained.

[0077] The upper limit of the content of phosphorus atoms (P) in the first resin composition is not particularly limited, and can be, for example, 5000 ppm or less.

[0078] In one embodiment, the content of sodium atoms (Na) in the first resin composition is 100 ppm or more, 150 ppm or more, 200 ppm or more, 400 ppm or more, 600 ppm or more, 800 ppm or more, or 1000 ppm or more. When the content of sodium atoms (Na) in the first resin composition is in the above range, the effect of excellent thermal stability is likely to be obtained.

[0079] The upper limit of the content of sodium atoms (Na) in the first resin composition is not particularly limited, and can be, for example, 5000 ppm or less.

[0080] In this specification, the phrase "containing a phosphorus atom (P) and a sodium atom (Na)" means that the resin composition may contain a phosphorus atom (P) and a sodium atom (Na) as free components.

[0081] The phosphorus atom (P) and the sodium atom (Na) may be free components as simple substances, or may be free components as compounds with other atoms, ions, etc. The contents of the phosphorus atom (P) and the sodium atom (Na) are the ratios to the total amount of the resin composition and the free components, and include the phosphorus atom (P) and the sodium atom (Na) contained in (B) the inorganic metal phosphate and its decomposition products.

[0082] The contents of phosphorus atoms (P) and sodium atoms (Na) are values ​​determined by inductively coupled plasma atomic emission spectrometry described in the examples.

[0083] The content of each component in the resin composition explained above can also be applied to the amount of each component blended during preparation of the resin composition. The radical amount of the aromatic polyether (A) explained above can also be applied to the radical amount of the aromatic polyether (A) during preparation of the resin composition (immediately before mixing with the inorganic metal phosphate (B)). Furthermore, the radical amount of the aromatic polyether (A) explained above can also be applied to the radical amount per unit mass of the resin composition. That is, in one embodiment, the resin composition 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.

[0084] [Second Resin Composition] A resin composition according to another embodiment of the present invention (hereinafter also referred to as "second resin composition") contains an aromatic polyether, a phosphorus atom (P), and a sodium atom (Na), 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.

[0085] The resin composition according to this embodiment can exhibit excellent interfacial adhesive strength to reinforcing fibers such as inorganic fillers, and also has excellent thermal stability. Furthermore, by using the resin composition in the production of composite materials and molded articles, composite materials and molded articles with excellent mechanical properties (e.g., tensile modulus and elongation) can be produced. The mechanical properties of the composite materials and molded articles can be measured according to the methods described in the examples.

[0086] The reason why such an effect is obtained is not entirely clear, but the radical amount of the resin composition is 6.5 × 10 １５ ~9.0 x 10 １７ It is presumed that the high spin / g of the resin composition causes interactions with the reinforcing fibers and the formation of chemical bonds. １５ ~9.0 x 10 １７At a high concentration of 10 ...

[0087] In this specification, unless otherwise specified, the "radical amount" of a resin composition means the "radical amount per unit mass (unit: spin / g)" of the resin composition.

[0088] In one embodiment, the radical amount of the resin composition 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, 8.9×10 １５ spin / g or more, 1.0×10 １６ spin / g or more, 2.0×10 １６ spin / g or more, 3.0×10 １６ spin / g or more, 4.0×10 １６ spin / g or more, or 5.0 x 10 １６ spin / g or more, and １７ spin / g or less, 5.0×10 １７ spin / g or less, 4.0×10 １７ spin / g, 3.7×10 １７ spin / g or less, or 1.0 x 10 １７ The radical amount of the resin composition is 6.5×10 １５ When the radical amount of the resin composition is 9.0×10 or more, the above-mentioned composite effect and the like are easily obtained, and the interfacial shear strength with the reinforcing fiber is easily obtained. １７ When the viscosity is less than or equal to spin / g, thermal stability is easily obtained and sufficient mechanical properties are easily exhibited as a molded article.

[0089] The radical amount of the resin composition can be increased to the above range, for example, by using an aromatic polyether having a large radical amount.

[0090] With regard to the aromatic polyether, the matters explained in relation to the aromatic polyether (A) in the first resin composition can be applied, except that there is no limitation on the radical amount.

[0091] The second resin composition contains phosphorus atoms (P) and sodium atoms (Na). The inclusion of phosphorus atoms (P) and sodium atoms (Na) in the resin composition can be confirmed by inductively coupled plasma atomic emission spectroscopy described in the examples.

[0092] In one embodiment, the content of phosphorus atoms (P) in the second resin composition is 100 ppm or more, 150 ppm or more, 200 ppm or more, 400 ppm or more, 600 ppm or more, 800 ppm or more, or 1000 ppm or more. When the content of phosphorus atoms (P) in the second resin composition is in the above range, the effect of excellent thermal stability is likely to be obtained.

[0093] The upper limit of the content of phosphorus atoms (P) in the second resin composition is not particularly limited, and can be, for example, 5000 ppm or less.

[0094] In one embodiment, the content of sodium atoms (Na) in the second resin composition is 100 ppm or more, 150 ppm or more, 200 ppm or more, 400 ppm or more, 600 ppm or more, 800 ppm or more, or 1000 ppm or more. When the content of sodium atoms (Na) in the second resin composition is in the above range, the effect of excellent thermal stability is likely to be obtained.

[0095] The upper limit of the content of sodium atoms (Na) in the second resin composition is not particularly limited, and can be, for example, 5000 ppm or less.

[0096] In this specification, the phrase "containing a phosphorus atom (P) and a sodium atom (Na)" means that the resin composition may contain a phosphorus atom (P) and a sodium atom (Na) as free components.

[0097] The phosphorus atom (P) and the sodium atom (Na) may be free components as simple substances, or may be free components as compounds with other atoms, ions, etc. The contents of the phosphorus atom (P) and the sodium atom (Na) are the ratios to the total amount of the resin composition and the free components.

[0098] The contents of phosphorus atoms (P) and sodium atoms (Na) are values ​​determined by inductively coupled plasma atomic emission spectrometry described in the examples.

[0099] The second resin composition may contain components other than the aromatic polyether, phosphorus atom (P), and sodium atom (Na) as long as the effects of the present invention are not impaired. Examples of other components in the second resin composition include an inorganic metal phosphate (B) and other resins other than aromatic polyethers. The matters described for the first resin composition can be applied to the inorganic metal phosphate (B) and other resins.

[0100] 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 resin composition is an aromatic polyether, phosphorus atoms (P), and sodium atoms (Na). 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 resin composition is an aromatic polyether, phosphorus atoms (P), sodium atoms (Na), and an amorphous resin. In addition, in the case of "substantially 100% by mass", inevitable impurities may be included.

[0101] The contents of each component in the resin composition explained above can also be applied to the blending amounts of each component when preparing the resin composition.

[0102] The complex viscosity and loss tangent (tan δ) of the second resin composition can be determined in the same manner as described for the first resin composition.

[0103] 2. Manufacturing Method of Resin Composition [First Manufacturing Method] A first manufacturing method of a resin composition according to one aspect of the present invention (hereinafter also referred to as "first manufacturing method of the present invention" or "first manufacturing method") includes a reaction step of reacting 4,4'-dichlorobenzophenone with hydroquinone in the presence of a reaction solvent to obtain an aromatic polyether, a washing step of washing the aromatic polyether obtained in the reaction step, an aromatic polyether drying step of drying the aromatic polyether obtained in the washing step, and a kneading step of melt-kneading 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) with 100 parts by mass of the aromatic polyether obtained in the aromatic polyether drying step to obtain a kneaded mixture.

[0104] According to the first production method according to one aspect of the present invention, a resin composition according to one aspect of the present invention can be obtained.

[0105] (Reaction Step) The reaction step is a step in which 4,4'-dichlorobenzophenone and hydroquinone are reacted in the presence of a reaction solvent to obtain an aromatic polyether.

[0106] [4,4'-Dichlorobenzophenone] 4,4'-Dichlorobenzophenone is a monomer for polymerizing aromatic polyethers and corresponds to the structural unit represented by the above formula (1). 4,4'-Dichlorobenzophenone can be easily synthesized and is also commercially available.

[0107] [Hydroquinone] Hydroquinone is a monomer for polymerizing aromatic polyethers and corresponds to the structural unit represented by the above formula (2). Hydroquinone can be easily synthesized and is also commercially available.

[0108] [Reaction Solvent] As the reaction solvent, 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, and the like.

[0109] In one embodiment, 4,4'-dichlorobenzophenone and hydroquinone are reacted with stirring in diphenyl sulfone in the presence of potassium carbonate to provide an aromatic polyether.

[0110] [Potassium Carbonate] Potassium carbonate preferably has a purity of 99% by mass or more and a water content of 0.01% by mass or less. Such potassium carbonate is also commercially available. Potassium carbonate may be of general-purpose reagent grade, general industrial grade, or fine particle grade. The average particle size (D ５０ The average particle size (D) is preferably 1000 μm or less, 800 μm or less, 500 μm or less, 300 μm or less, 100 μm or less, or even 50 μm or less. ５０ The lower limit of the average particle size (D ５０ ) is a value measured by the following method.５０ Measurement method for particle size distribution] Using a CAMSIZER manufactured by Microtrac Bell Co., Ltd., particle size distribution is measured by a dry method. A sample (potassium carbonate) is dropped into the measurement section using a vibrating feeder, and the particles are photographed with a camera to measure the particle diameter. When processing the observed image, the average particle diameter (D ５０ ) is calculated.

[0111] The reaction step can be carried out in an inert gas atmosphere, which is not particularly limited and includes, for example, nitrogen, argon gas, etc.

[0112] The reaction of the raw material mixture containing 4,4'-dichlorobenzophenone and hydroquinone can be carried out under heating. The reaction temperature can usually be in the range of 150 to 380°C. The reaction time can usually be 0.1 to 10 hours. The time to terminate the reaction can also be determined using the viscosity value of the reaction solution (raw material mixture in which the reaction has progressed) as an indicator. If the reaction is terminated when the solution viscosity is 100 cP or higher, a high molecular weight product is likely to be obtained. The solution viscosity is measured using a process viscometer (XL7-951-HT2-d28-E58 manufactured by Hydramotion Japan Co., Ltd.) or the like.

[0113] In one embodiment, the raw material mixture is heated to 150°C or higher and then maintained at that temperature. In one embodiment, the raw material mixture is heated to 150°C or higher and then the heating and temperature maintenance are repeated multiple times. In each of the above embodiments, the heating after heating to 150°C or higher may be performed at a rate of 10°C / min or less. This allows the rate-determining step in the reaction of the raw material mixture to proceed smoothly, making it easier to obtain a high molecular weight aromatic polyether.

[0114] The reaction of the raw material mixture may include, for example, (i) a step of increasing the temperature to 180 to 220°C and maintaining the increased temperature for 0.5 to 2 hours, (ii) a step of increasing the temperature to 230 to 270°C and maintaining the increased temperature for 0.5 to 2 hours, and (iii) a step of increasing the temperature to 280 to 320°C and maintaining the increased temperature for 1 to 8 hours.

[0115] The temperature increase in (i) to (iii) can be carried out at a rate of, for example, 10°C / min or less, 5°C / min or less, or 3°C / min or less. The temperature increase in (i) to (iii) is preferably, for example, 0.1 to 10°C / min or less. This allows the rate-determining step in the reaction of the raw material mixture to proceed smoothly, and makes it easier to obtain a high molecular weight aromatic polyether.

[0116] In one embodiment, the reaction of the raw material mixture can include at least one step selected from the group consisting of the above-mentioned steps (i) to (iii). When two or three steps are included, the steps are preferably performed in order from lowest to highest temperature. Between two or three steps, the raw material mixture can be heated.

[0117] In one embodiment, the reaction of the raw material mixture is carried out under conditions in which the maximum temperature of the raw material mixture is 280 to 320°C, more preferably higher than 290°C and not higher than 320°C.

[0118] After the reaction of the raw material mixture is completed, the aromatic polyether can be separated, washed, or purified according to known methods.

[0119] (Washing Step) The washing step is a step of washing the aromatic polyether obtained in the reaction step with a washing solvent. In the washing step, washing may be performed once, washing may be performed multiple times using one type of washing solvent, or washing with two or more types of washing solvents may be performed in combination. Examples of the washing solvent include water, an acid aqueous solution, and an organic solvent.

[0120] The acid used in the acid aqueous solution is not particularly limited, and examples thereof include oxalic acid, hydrochloric acid, acetic acid, phosphoric acid, etc. The acid may be used alone or in combination of two or more kinds.

[0121] The concentration of the acid in the acid aqueous solution is not particularly limited and can be set appropriately, for example, from 0.001N to 5N.

[0122] Examples of organic solvents include carbonates such as propylene carbonate, ethylene carbonate, butylene carbonate, dimethyl carbonate, diethyl carbonate, and methyl ethyl carbonate; lactones such as γ-butyrolactone; ethers such as trimethoxymethane, 1,2-dimethoxyethane, diethyl ether, 2-ethoxyethane, tetrahydrofuran, and 2-methyltetrahydrofuran; sulfoxides such as dimethyl sulfoxide; oxolanes such as 1,3-dioxolane and 4-methyl-1,3-dioxolane; Examples of suitable organic solvents include nitrogen-containing solvents such as nitriles, nitromethane, and N-methyl-2-pyrrolidone; esters such as methyl formate, methyl acetate, butyl acetate, methyl propionate, ethyl propionate, and phosphate triesters; glymes such as diglyme, triglyme, and tetraglyme; ketones such as acetone, diethyl ketone, methyl ethyl ketone, and methyl isobutyl ketone; sulfones such as sulfolane; oxazolidinones such as 3-methyl-2-oxazolidinone; and sultones such as 1,3-propane sultone, 4-butane sultone, and naphtha sultone. Among these, acetone is preferred as the organic solvent. These organic solvents may be used alone or in combination of two or more.

[0123] In the washing step, for example, the reaction product containing the aromatic polyether is washed with acetone, an aqueous oxalic acid solution, and water in this order, which is preferable because it can effectively remove residual monomers and solvents in the aromatic polyether, as well as potassium atoms (K), sodium atoms (Na), alkali metal atoms, and the like.

[0124] (Aromatic Polyether Drying Step) The aromatic polyether drying step is a step of removing the solvent from the aromatic polyether. The solvent to be removed is not limited to the washing solvent, but also includes, for example, the remaining reaction solvent. It is not necessary to completely remove the solvent from the aromatic polyether, and at least a portion of the solvent may be removed. For example, the step may remove 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more of the solvent in the aromatic polyether.

[0125] As the drying means, a known dryer, a thermo-hygrostat, etc. can be used. The drying method is not particularly limited, and a vibration dryer, a hot air dryer, a vacuum dryer, an airflow dryer, etc. can be used.

[0126] Drying can be carried out at a temperature depending on the type of solvent remaining in the aromatic polyether, for example, at a temperature equal to or higher than the boiling point of the remaining solvent. The drying temperature can be selected from, for example, 50 to 250°C, 80 to 200°C, or 100 to 180°C. Alternatively, drying can be performed by reduced pressure drying (vacuum drying) using a vacuum pump or the like. The drying time is not particularly limited, but can be selected, for example, from 1 minute or more, 10 minutes or more, 30 minutes or more, or 1 hour or more. The upper limit of the drying time is also not particularly limited, but can be selected, for example, from 24 hours or less, 12 hours or less, 6 hours or less, or 3 hours or less. A filtration step may be added before drying to remove the solvent. Adding a filtration step can reduce the amount of solvent to be removed, thereby reducing the process time, drying time, and dryer capacity, thereby reducing the environmental impact and efficiently obtaining an aromatic polyether from which the solvent has been removed.

[0127] (Kneading Step) The kneading step is a step in which 100 parts by mass of the aromatic polyether obtained in the aromatic polyether drying step is melt-kneaded with 0.01 to 5.0 parts by mass of the inorganic metal phosphate (B) to obtain a kneaded product.

[0128] The inorganic metal phosphate (B) can be applied to the resin composition according to one embodiment of the present invention.

[0129] The mode of melt-kneading is not particularly limited, but for example, inorganic metal phosphate (B) is kneaded with molten aromatic polyether. The method of kneading inorganic metal phosphate (B) is not particularly limited, but examples thereof include melt-kneading using an extruder, etc. The inorganic metal phosphate (B) may be side-fed into the aromatic polyether using a twin-screw kneader.

[0130] [Second Production Method] A second production method for a resin composition according to one embodiment of the present invention (hereinafter also referred to as "the second production method of the present invention" or "second production method") includes: a reaction step of reacting 4,4'-dichlorobenzophenone with hydroquinone in the presence of a reaction solvent to obtain an aromatic polyether; a washing step of washing the aromatic polyether obtained in the reaction step; a mixing step of mixing 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) with 100 parts by mass of the aromatic polyether obtained in the washing step in the presence of a solvent to obtain a mixture; and a mixture drying step of drying the mixture obtained in the mixing step.

[0131] According to the second production method according to an aspect of the present invention, a resin composition according to an aspect of the present invention can be obtained.

[0132] The reaction step and the washing step can be applied to the same as those described in the first manufacturing method according to one embodiment of the present invention.

[0133] (Mixing Step) The mixing step is a step in which 100 parts by mass of the aromatic polyether obtained in the washing step is mixed with 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) in the presence of a solvent to obtain a mixture. The aromatic polyether obtained in the washing step may contain a solvent and may be in the form of, for example, a cake or slurry of resin (aromatic polyether) / solvent. When in the form of a cake or slurry of resin (aromatic polyether) / solvent, 100 parts by mass of the aromatic polyether means 100 parts by mass of the aromatic polyether remaining after excluding the solvent portion from the entire cake or slurry.

[0134] The inorganic metal phosphate (B) can be applied to the resin composition according to one embodiment of the present invention.

[0135] Examples of solvents that can be used in the mixing step include water, acetone, methyl ethyl ketone, cyclohexanone, and N-methyl-2-pyrrolidone. The above-mentioned solvents may be used alone or in combination of two or more. From the viewpoint of the solubility of the inorganic phosphate, it is preferable to use water alone or a mixed solution of water and acetone.

[0136] In one embodiment, the mixing is carried out in the presence of 50 to 1000 parts by weight, 100 to 800 parts by weight, or 300 to 700 parts by weight of a solvent per 100 parts by weight of the aromatic polyether.

[0137] (Mixture Drying Step) The mixture drying step is a step of removing the solvent from the mixture obtained in the mixing step. The solvent to be removed is not limited to the solvent used in the mixing step, but also includes, for example, the remaining reaction solvent and washing solvent. It is not necessary to completely remove the solvent from the mixture, and at least a portion of the solvent may be removed. For example, the mixture drying step may remove 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more of the solvent in the mixture.

[0138] As the drying means, a known dryer, a thermo-hygrostat, etc. can be used. The drying method is not particularly limited, and a vibration dryer, a hot air dryer, a vacuum dryer, an airflow dryer, etc. can be used.

[0139] Drying can be performed at a temperature appropriate for the type of solvent remaining in the mixture, for example, at a temperature equal to or higher than the boiling point of the remaining solvent. The drying temperature can be selected from, for example, 50 to 250°C, 80 to 200°C, or 100 to 180°C. Alternatively, the mixture can be dried under reduced pressure (vacuum drying) using a vacuum pump or the like. The drying time is not particularly limited, but can be selected, for example, from 1 minute or more, 10 minutes or more, 30 minutes or more, or 1 hour or more. The upper limit of the drying time is also not particularly limited, but can be selected, for example, from 24 hours or less, 12 hours or less, 6 hours or less, or 3 hours or less. A filtration step may be added before drying to remove the solvent. Adding a filtration step reduces the amount of solvent to be removed, shortening the process time, drying time, and reducing the capacity of the dryer, thereby reducing the environmental impact and efficiently obtaining a resin composition.

[0140] The method for producing a resin composition according to one embodiment of the present invention may employ steps, methods, conditions, etc. that are commonly used in the field of resin compositions, as long as the effects of the present invention are not impaired.

[0141] 3. Composite Material A composite material according to one aspect of the present invention comprises the resin composition according to one aspect of the present invention (first resin composition and / or second resin composition) and 0.01 to 500 parts by mass of reinforcing fibers (C) per 100 parts by mass of the resin composition. The composite material according to this aspect has excellent interfacial shear strength between the resin composition and the reinforcing fibers, and therefore exhibits excellent mechanical properties (e.g., tensile modulus and elongation) as a composite material.

[0142] (Reinforcing fiber (C)) In one embodiment, the content of the reinforcing fiber (C) in the composite material is 0.01 parts by mass or more, 0.1 parts by mass or more, 1 part by mass or more, or 10 parts by mass or more, and 500 parts by mass or less, 300 parts by mass or less, 200 parts by mass or less, or 100 parts by mass or less, relative to 100 parts by mass of the resin composition. When the content of the reinforcing fiber relative to 100 parts by mass of the resin composition is 0.01 parts by mass or more, the reinforcing effect of the reinforcing fiber is more easily obtained, and when it is 500 parts by mass or less, the suitability for kneading and molding the composite material is more easily improved.

[0143] In one embodiment, the reinforcing fibers (C) comprise 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 (C) are one or more selected from the group consisting of carbon fibers, glass fibers, and aramid fibers.

[0144] 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).

[0145] The carbon fibers may be treated with a sizing agent. The sizing agent can bind the reinforcing fibers into a bundle. Reinforcing fibers treated with a sizing agent have the sizing agent adhered to their surfaces. The sizing agent is not particularly limited, and examples include epoxy-based sizing agents, urethane-based sizing agents, and polyamide-based sizing agents. Aromatic polyethers can also be used as the sizing agent. These sizing agents may be used alone or in combination of two or more. Reinforcing fibers that have not been treated with a sizing agent may also be used. The sizing agent may be used in combination with a silane coupling agent such as aminosilane, isocyanate silane, or acrylic silane.

[0146] The type of glass fiber or aramid fiber is 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.

[0147] The glass fibers may also be treated with a sizing agent. The sizing agent can bind the glass fibers into bundles. The glass fibers treated with a sizing agent have the sizing agent adhered to their surfaces. The sizing agent is not particularly limited, and examples thereof include epoxy-based sizing agents, urethane-based sizing agents, and vinyl acetate-based sizing agents. Aromatic polyethers can also be used as sizing agents. These sizing agents may be used alone or in combination of two or more. Glass fibers that have not been treated with a sizing agent may also be used. The sizing agent may be used in combination with a silane coupling agent such as aminosilane, isocyanate silane, or acrylic silane.

[0148] From the viewpoint of the mechanical properties of the molded body, such as strength, elastic modulus, and impact resistance, the average fiber length of the reinforcing fibers (C) in the composite material is preferably 5 mm or more. When the average fiber length of the reinforcing fibers (C) is 5 mm or more, they are also called "continuous fibers." The average fiber length is determined by the arithmetic mean of values ​​measured with a vernier caliper.

[0149] The composite material may contain other components that do not fall under the category of the resin composition and the reinforcing fiber (C). The other components are not particularly limited, and examples thereof include other resins that are not aromatic polyethers. Examples of other resins include fluororesins such as polytetrafluoroethylene. One type of other component may be used alone, or two or more types may be used in combination.

[0150] 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 composite material is the resin composition and the reinforcing fiber (C), or the resin composition, the reinforcing fiber (C), and the other components described above.

[0151] In one embodiment, the composite material may be a fiber composite material including a resin composition as a matrix and reinforcing fibers (C). The fiber composite material may be a so-called fiber reinforced thermoplastic (FRTP).

[0152] The method for producing the composite material (composite method) is not particularly limited. For example, a method of melt-kneading the resin composition and the reinforcing fibers (C), or a method of melting and impregnating an aggregate of the reinforcing fibers (C) with one or more resin compositions in a powder, film, or pellet form may be used. The reinforcing fibers (C) may be side-fed into the resin composition using a twin-screw kneader. The aggregate of the reinforcing fibers (C) may be in one or more forms selected from the group consisting of a woven fabric, a nonwoven fabric, and a unidirectional material (also referred to as a "UD material"). In these forms, the average fiber length of the reinforcing fibers (C) may be 5 mm or more. That is, the reinforcing fibers (C) may be continuous fibers. This further improves the strength of the composite material.

[0153] Pellets of the composite material may be produced. The pellets can be used as a raw material for producing a molded body, which will be described later. In one embodiment, the method for producing pellets includes cutting the reinforcing fibers (C) short to form chopped strands, and then adding a resin composition to the reinforcing fibers (C). The short fibers and the resin composition are mixed and granulated to produce pellets (also referred to as "short fiber pellets"). In one embodiment, the method for producing pellets includes immersing a roving of the reinforcing fibers (C) in a molten resin composition, pultrusion molding the mixture, and then cutting the roving into a desired pellet length to produce pellets (also referred to as "long fiber pellets"). When long fiber pellets are produced as described above, breakage of the reinforcing fibers (C) can be suppressed.

[0154] 4. Molded Article A molded article according to one embodiment of the present invention is made from the resin composition according to one embodiment of the present invention. According to the molded article according to this embodiment, the breakage of the aromatic polyether (A) in the resin composition is suppressed by the inorganic metal phosphate (B) or by phosphorus atoms and sodium atoms, thereby achieving excellent mechanical properties (e.g., tensile modulus and elongation). Furthermore, when the molded article according to this embodiment is used in combination with reinforcing fibers (C), excellent interfacial shear strength with the reinforcing fibers (C) is achieved.

[0155] A molded article according to another aspect of the present invention is made from the composite material according to one aspect of the present invention. The molded article according to this aspect exhibits excellent interfacial shear strength between the resin composition and the reinforcing fibers (C) in the composite material, resulting in excellent mechanical properties (e.g., tensile modulus and elongation). The reinforcing fibers (C) can be the same as those described for the composite material according to one aspect of the present invention.

[0156] 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, 100% by mass or less, 99.9% by mass or less, or substantially 100% by mass of the molded article is a resin composition, a resin composition and reinforcing fibers (C), or a resin composition, reinforcing fibers (C), and the other components described above. Note that when it is "substantially 100% by mass", it may contain inevitable impurities.

[0157] 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").

[0158] The method for producing a molded article according to one embodiment of the present invention is not particularly limited. For example, a molded article can be produced by molding the resin composition or composite material according to one embodiment of the present invention (which may be in the form of pellets as described above). Known methods such as injection molding, extrusion molding, and blow molding can be used for molding. The composite material can also be press-molded, and known methods such as cold pressing and hot pressing can be used. Furthermore, the composite material can be used as a resin composite material for a 3D printer and molded using a 3D printer.

[0159] The uses of the resin composition, composite material, and molded article described above are not particularly limited and can be widely applied to, for example, various uses requiring strength. The resin composition, composite material, and molded article are suitable, for example, as metal replacement materials, particularly for uses requiring heat resistance, solvent resistance, and durability. More specifically, they are suitable, for example, for bearings, gaskets, structural materials, and the like.

[0160] Examples of the present invention will be described below, but the present invention is not limited to these examples.

[0161] (Production Example 1) 1. Synthesis of Aromatic Polyether 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, 39.00 kg (155 mol) of 4,4'-dichlorobenzophenone (manufactured by Sino-High Corporation), 16.85 kg (153 mol) of hydroquinone, and 21.78 kg (158 mol) of potassium carbonate (AGC Corporation, fine powder) were added in that order. The reaction concentration at this time was 2.31 mol / kg.

[0162] The reaction mixture was reacted under the following temperature control, and then 6.15 kg (25 moles) of 4,4'-dichlorobenzophenone was added as a reaction terminator. <Temperature control> (1) At a stirring speed of 100 rpm, the temperature was raised from 160°C to 200°C over 90 minutes. (2) The temperature was maintained at 200°C for 60 minutes. (3) The temperature was raised from 200°C to 250°C over 80 minutes. (4) The temperature was maintained at 250°C for 60 minutes. (5) The temperature was raised from 250°C to 300°C over 150 minutes. (6) The temperature was maintained at 300°C for 263 minutes. (7) The reaction terminator was added, and the temperature was maintained at 300°C. The reaction was terminated when the solution viscosity reached 295 cP.

[0163] After the reaction was completed, the contents were transferred to a SUS tray, cooled to room temperature, and solidified. The product was coarsely pulverized and pulverized in a pin mill (160UPZ, manufactured by Hosokawa Micron Corporation), washed with acetone, an aqueous oxalic acid solution, and water in that order, and then vacuum dried to obtain a powdery aromatic polyether.

[0164] 2. Evaluation of Aromatic Polyethers The resulting aromatic polyethers were evaluated for the radical amount, melt flow rate, and potassium atom (K) content by the following methods. The results are shown in Table 1.

[0165] (1) Radical Amount The radical amount of aromatic polyether (measured at 25°C 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 to 344 mT Measurement time: 60 seconds Mn intensity: 650 Measurement temperature: 25°C

[0166] [Procedure] TEMPOL (4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl) was dissolved in benzene to a concentration of 5 μM, and 400 μL of this solution was added to an ESR sample tube. ESR was measured under the above-mentioned measurement conditions. The integral of the peak derived from TEMPOL obtained was divided by the integral of the peak of Mn for normalization (integral value A). The measurement sample was then weighed (weighed value B), loaded into an ESR sample tube, and ESR was measured under the above-mentioned measurement conditions. The integral of the peak derived from the sample obtained was divided by the integral of the peak of Mn for normalization (integral value C). The obtained values ​​of A, B, and C were used to calculate the amount of radicals per unit mass of the sample (radical concentration) according to the following formula: Amount of radicals [spin / g] = (5 x 10 －６ x400 x 10 －６ x 6.02 x 10 ２３ × C) / (A × B)

[0167] (2) Melt Flow Rate Using a melt indexer (L-220) manufactured by Tateyama Kagaku High-Technologies Corporation, the MFR of the aromatic polyether was measured under the following measurement conditions in accordance with JIS K 7210-1:2014 (ISO 1133-1:2011). [Measurement Conditions] Measurement temperature (resin temperature): 380°C Measurement load: 2.16 kg Cylinder inner diameter: 9.550 mm Die inner diameter: 2.095 mm Die length: 8.000 mm Piston head length: 6.35 mm Piston head diameter: 9.474 mm Piston weight: 110.0 g (the above measurement load includes the piston weight) Procedure: The sample was dried in advance at 150°C for more than 2 hours. The sample was placed in the cylinder, the piston was inserted, and the sample was preheated in the cylinder for 4 minutes. Next, a load was applied, the piston guide was removed, and the molten sample was extruded from the die. Samples were cut out at predetermined ranges of piston movement and predetermined times (t [s]), and their masses were measured (m [g]). The MFR was calculated using the following formula: MFR [g / 10 min] = 600 / t × m

[0168] (3) Potassium Atom (K) Content Aromatic polyether was dissolved under the following pretreatment conditions, and the K content was measured by ICP atomic emission spectroscopy. The quantitative value was determined based on a calibration curve prepared from a reference of known concentration, and the calibration curve solution had the same hydrochloric acid concentration as the sample solution. <Pretreatment Conditions> 0.1 to 1 g of sample was placed on a platinum dish, to which concentrated sulfuric acid was added and heated for carbonization, and then placed in an electric furnace for ashing at 550°C for 12 hours. Hydrochloric acid was added to the sample for heat treatment, and after cooling, the sample was made up to a constant volume with ultrapure water. <Measurement Conditions> ICP atomic emission spectroscopy analyzer: 5100 manufactured by Agilent Technologies, Inc. K measurement wavelength: 766.491 nm

[0169] (Production Example 2) A commercially available aromatic polyether (PEEK, manufactured by Victrex, 450G) was evaluated for the radical amount, melt flow rate, and potassium atom (K) content in the same manner as in Example 1. The results are shown in Table 1.

[0170] (Example 1) 1. Kneading of aromatic polyether 100 parts by mass of the aromatic polyether obtained in Production Example 1, inorganic metal phosphate NaH ２P.O. ４ 0.6 parts by mass, and inorganic metal phosphate Na ２ HPO ４ The dry blend raw material obtained by dry blending 0.4 parts by mass was melt-kneaded using a twin-screw extruder having a cylinder diameter of 11 mm ("Process-11" manufactured by ThermoFisher Scientific, cylinder volume 20 cc) at a screw rotation speed of 200 rpm and a set temperature of 380 ° C. Here, 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 strand discharged from the twin-screw extruder was cooled in water and then pelletized using a pelletizer to obtain a resin composition.

[0171] 2. Evaluation of Resin Compositions (1) Complex Viscosity and Loss Tangent (tan δ) The complex viscosity and loss tangent (tan δ) of the resulting resin compositions were measured using a viscoelasticity measuring device under the following conditions and procedures. The values ​​1 minute (1 min) and 60 minutes (60 min) after the start of measurement are shown in Table 1. The quotient obtained by dividing the complex viscosity at 60 min by the complex viscosity at 1 min is also shown in Table 1 as the viscosity increase rate.

[0172] [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: 380°C, 400°C, or 420°C Preheating time: 3 min Gap: 0.8 mm Time: 300 min Shear strain: 1% Angular frequency: 2.76 rad / s

[0173] [Procedure] A disk-shaped resin composition was placed on a disposable dish and measured under the conditions described above. For the measurement, the disk was sandwiched between the disposable dish and a disposable plate with a gap of 0.8 mm, preheated, and then trimmed to a diameter of 25 mm.

[0174] The "disc" was obtained by the following method: The resin composition was filled into a mold and pressed at a temperature of 380°C using a vacuum press (IMC-6215 manufactured by Imoto Machinery Co., Ltd.). After pressing, it was quenched at 25°C to form a disk with a diameter of 25 mm and a thickness of 1.0 mm.

[0175] (2) Radical Amount The radical amount of the resin composition was measured in the same manner as in "2. Evaluation of aromatic polyether," except that a resin composition was used as the measurement sample instead of an aromatic polyether. The results are shown in Table 1.

[0176] (3) Sodium Atom (Na) Content, Phosphorus Atom (P) Content The Na and P contents in the resin composition were dissolved under the following pretreatment conditions and measured by inductively coupled plasma atomic emission spectroscopy. Quantitative values ​​were obtained using a calibration curve derived from a reference of known concentration. <Pretreatment Conditions> 0.1 g of the resin composition was weighed into a quartz container as a sample. Next, nitric acid was added and the container was sealed. The container was then placed in a microwave decomposition device (Milestone General's "UltraWAVE" or equivalent) and irradiated with microwaves to perform pressure acid decomposition. The pressure acid decomposition rate was measured, and ultrapure water was added to the container to determine the volume. <Measurement Conditions> - ICP atomic emission spectroscopy device (Agilent Technologies' "Agilent 5100") - Na measurement wavelength: 589.592 nm - P measurement wavelength: 213.618 nm

[0177] The detection limit (lower detection limit) of the elemental analysis is 1 ppm. In Table 1 shown later, "N.D." (Not Detected) means below the detection limit (i.e., less than 1 ppm).

[0178] 3. Production of Molded Article The obtained resin composition pellets were injection molded using an injection molding machine ("Mini Jet Pro" manufactured by Thermo Fisher Scientific) under the following conditions to obtain ISO527-2-1BA tensile test specimens. <Injection conditions> (1) Cylinder temperature: 400°C (2) Mold temperature: 210°C (3) Preheating time: 3 min (4) Pressure holding time: 10 s

[0179] 4. Evaluation of Molded Articles Tensile tests were performed on the obtained test pieces under the following conditions to measure the maximum tensile strength, tensile modulus, and breaking strain (tensile elongation). The results are shown in Table 1. <Tensile conditions> Temperature: 23°C Speed: 20 mm / min Chuck distance: 50 mm Larger values ​​for the maximum tensile strength, tensile modulus, and breaking strain (tensile elongation) indicate better mechanical properties.

[0180] Example 2: Inorganic metal phosphate NaH ２ P.O. ４ 0.3 parts by mass of inorganic metal phosphate salt Na ２ HPO ４ A resin composition was obtained in the same manner as in Example 1, except that the amounts of the hydroxybenzoates and hydroxybenzoates were changed to 0.2 parts by mass. The complex viscosity, loss tangent (tan δ), radical amount, sodium atom (Na) content, and phosphorus atom (P) content of the obtained resin composition were evaluated in the same manner as in Example 1. The results are shown in Table 1.

[0181] Example 3: Inorganic metal phosphate NaH ２ P.O. ４ 0.06 parts by mass of inorganic metal phosphate salt Na ２ HPO ４ A resin composition was obtained in the same manner as in Example 1, except that the amounts of the hydroxybenzoates and hydroxybenzoates were changed to 0.04 parts by mass. The complex viscosity, loss tangent (tan δ), radical amount, sodium atom (Na) content, and phosphorus atom (P) content of the obtained resin composition were evaluated in the same manner as in Example 1. The results are shown in Table 1.

[0182] (Comparative Example 1) NaH ２ P.O. ４ and Na ２ HPO ４Aromatic polyether pellets were obtained in the same manner as in Example 1, except that the dry blending of the above was omitted. The complex viscosity, loss tangent (tan δ), radical amount, sodium atom (Na) content, and phosphorus atom (P) content of the obtained aromatic polyether were evaluated in the same manner as in Example 1. The results are shown in Table 1. Furthermore, the obtained aromatic polyether was injection molded under the same conditions as in Example 1 to obtain ISO 527-2-1BA tensile test specimens. A tensile test was performed on the obtained test specimens under the same conditions as in Example 1 to measure the maximum tensile strength, tensile modulus, and breaking strain (tensile elongation). The results are shown in Table 1.

[0183] Comparative Example 2 The aromatic polyether of Production Example 2 (PEEK, manufactured by Victrex, 450G) was evaluated for complex viscosity, loss tangent (tan δ), radical amount, sodium atom (Na) content, and phosphorus atom (P) content in the same manner as in Example 1. The results are shown in Table 1. Furthermore, injection molding was performed using the aromatic polyether of Production Example 2 under the same conditions as in Example 1 to obtain ISO 527-2-1BA tensile test specimens. A tensile test was performed on the obtained test specimens under the same conditions as in Example 1 to measure the maximum tensile strength, tensile modulus, and breaking strain (tensile elongation). The results are shown in Table 1.

[0184]

[0185] From Table 1, it can be seen that the molded body produced in Example 1 has superior mechanical properties (tensile modulus, elongation) compared to the molded body produced in Comparative Example 1. It can also be seen that the resin compositions used in Examples 1 to 3 have superior thermal stability compared to the case where an inorganic metal phosphate is not contained (the aromatic polyether used in Comparative Example 1). Furthermore, the aromatic polyether of Production Example 1 used in Examples 1 to 3 has a significantly larger amount of radicals than the aromatic polyether of Production Example 2 used in Comparative Example 2, and when composited, it can be expected that the interfacial shear strength between the aromatic polyether and the reinforcing fiber will be excellent.

[0186] (Production Example 3) Synthesis of aromatic polyether was carried out in the same manner as in Production Example 1, except that (6) and (7) of <Temperature Control> in Production Example 1 were changed as follows: <Temperature Control> (1) to (5) were the same as in Production Example 1 (6) Maintained at 300°C for 213 minutes (7) A reaction terminator was added and the temperature was maintained at 300°C for 1 hour, after which the reaction was terminated

[0187] After the reaction was completed, the contents were transferred to a SUS tray and cooled to room temperature to solidify. 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, in that order, to obtain a wet resin / water cake. A portion of the product was dried at 150°C for 5 hours, and the amount of water in the dried cake was 72.6% by mass and the amount of resin was 27.4% by mass. The amount of radicals was evaluated in the same manner as in Example 1, and was found to be 1.3 x 10 １６ spin / g.

[0188] Comparative Example 3 The dried cake obtained in Production Example 3 was used as a resin of Comparative Example 3 to which no phosphate was added. The melt flow rate was evaluated in the same manner as in Production Example 1 and was found to be 19 g / 10 min.

[0189] The complex viscosity and loss tangent (tan δ) of the resulting resin were evaluated in the same manner as in Example 1. The results are shown in Table 2.

[0190] Example 4 Water was added to the resin / water cake of Production Example 3 so that the total amount of water was 65 parts by mass per 12 parts by mass of resin. ２ P.O. ４ 0.057 parts by mass of inorganic metal phosphate sodium ２ HPO ４ 0.039 parts by mass of ethanol was added and mixed for 20 minutes at 50 to 60° C. After mixing, the mixture was filtered and the amount of water recovered was 35 parts by mass. The recovered cake was dried at 150° C. for 5 hours.

[0191] NaH relative to 100 parts by mass of resin ２ P.O. ４ and Na ２ HPO ４ The content of phosphate was evaluated based on the following calculation formula:２ P.O. ４ :0.2 parts by mass, Na ２ HPO ４ Amount of phosphate in resin = ((total amount of water - amount of water recovered by filtration) / total amount of water) × 100 / 12

[0192] The complex viscosity and loss tangent (tan δ) of the obtained resin composition were evaluated in the same manner as in Comparative Example 3. The results are shown in Table 2.

[0193] Example 5 In Example 4, the total amount of water was changed to 72 parts by mass, and the inorganic metal phosphate NaH ２ P.O. ４ 0.112 parts by mass of inorganic metal phosphate sodium ２ HPO ４ The same operation as in Example 4 was carried out, except that the amount of water was 0.075 parts by mass. After mixing, the mixture was filtered and the amount of water recovered was 42 parts by mass. The content of phosphate relative to 100 parts by mass of resin was 0.075 parts by mass of NaH ２ P.O. ４ :0.4 part by mass, Na ２ HPO ４ : 0.3 parts by mass.

[0194] The complex viscosity and loss tangent (tan δ) of the obtained resin composition were evaluated in the same manner as in Comparative Example 3. The results are shown in Table 2.

[0195] Example 6 In Example 4, the total amount of water was changed to 87 parts by mass, and the inorganic metal phosphate NaH ２ P.O. ４ 0.227 parts by mass of inorganic metal phosphate sodium ２ HPO ４ The same operation as in Example 4 was carried out, except that the amount of water was 0.153 parts by mass. After mixing, the mixture was filtered and the amount of water recovered was 57 parts by mass. The content of phosphate relative to 100 parts by mass of resin was 0.153 parts by mass. ２ P.O. ４ :0.7 parts by mass, Na ２ HPO ４ : 0.4 parts by mass.

[0196] The complex viscosity and loss tangent (tan δ) of the obtained resin composition were evaluated in the same manner as in Comparative Example 3. The results are shown in Table 2.

[0197]

[0198] From Table 2, it can be seen that the resin compositions obtained in Examples 4 to 6 have superior thermal stability compared to the resin not containing an inorganic metal phosphate (resin produced in Comparative Example 3).

[0199] 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. The standard substance was TEMPOL, and the solvent for the standard substance was benzene. The amount of radicals at 25°C was 6.5 x 10 １５ ~9.0 x 10 １７ The resin composition comprises an aromatic polyether (A) having a molecular weight of 10 ...

2. The resin composition according to claim 1, wherein the aromatic polyether (A) is a polyarylene ether ketone.

3. The resin composition according to claim 1 or 2, wherein the aromatic polyether (A) comprises at least one selected from the group consisting of polyether ether ketone (PEEK) and polyether ketone (PEK).

4. The resin composition according to any one of claims 1 to 3, wherein the inorganic metal phosphate (B) contains an alkali metal.

5. The resin composition according to any one of claims 1 to 4, wherein the inorganic metal phosphate (B) contains two or more metal species.

6. A compound containing aromatic polyether, phosphorus (P), and sodium (Na) atoms, measured using TEMPOL as the standard substance and benzene as the solvent, had a radical content of 6.5 x 10 at 25°C. １５ ~9.0 x 10 １７ The resin composition has a viscosity of 1000 MPa (spin / g).

7. A resin composition according to any one of claims 1 to 6, wherein the content of sodium atoms (Na) is 100 ppm or more.

8. The resin composition according to any one of claims 1 to 7, wherein the content of phosphorus atoms (P) is 100 ppm or more.

9. The resin composition according to any one of claims 1 to 8, wherein the complex viscosity of the resin composition measured using a viscoelasticity measuring device at a set temperature of 420°C satisfies the following formula (R1): complex viscosity after 60 minutes of measurement / complex viscosity after 1 minute of measurement≦2.0 (R1) 10. The resin composition according to any one of claims 1 to 9, which has a loss tangent (tanδ) of 0.5 or more after measurement for 60 minutes at a set temperature of 420°C using a viscoelasticity measuring device.

11. The resin composition according to any one of claims 1 to 10, wherein the complex viscosity and loss tangent (tan δ) after measurement for 60 minutes at a set temperature of 420°C using a viscoelasticity measuring device satisfy the following formula (R2): Loss tangent (tan δ) × complex viscosity ≦ 7500 (R2) 12. A composite material comprising the resin composition according to any one of claims 1 to 11 and 0.01 to 500 parts by mass of reinforcing fiber (C) per 100 parts by mass of the resin composition.

13. The composite material according to claim 12, wherein the reinforcing fibers (C) comprise at least one selected from the group consisting of carbon fibers, glass fibers, and aramid fibers.

14. A composite material according to claim 12 or 13, wherein the reinforcing fibers (C) in the composite material have an average fiber length of 5 mm or more.

15. A molded article made from the resin composition according to any one of claims 1 to 11.

16. A molded article made of the composite material according to any one of claims 12 to 14.

17. The molded article according to claim 15 or 16, which is an injection molded article.

18. The molded article according to claim 15 or 16, wherein the molded article is an extruded molded article.

19. The molded body according to claim 15 or 16, wherein the molded body is a compression molded body.

20. A method for producing a resin composition, comprising: a reaction step of reacting 4,4'-dichlorobenzophenone with hydroquinone in the presence of a reaction solvent to obtain an aromatic polyether; a washing step of washing the aromatic polyether obtained in the reaction step; an aromatic polyether drying step of drying the aromatic polyether obtained in the washing step; and a kneading step of melt-kneading 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) with 100 parts by mass of the aromatic polyether obtained in the aromatic polyether drying step to obtain a kneaded mixture.

21. A method for producing a resin composition, comprising: a reaction step of reacting 4,4'-dichlorobenzophenone with hydroquinone in the presence of a reaction solvent to obtain an aromatic polyether; a washing step of washing the aromatic polyether obtained in the reaction step; a mixing step of mixing 0.01 to 5.0 parts by mass of an inorganic metal phosphate (B) with 100 parts by mass of the aromatic polyether obtained in the washing step in the presence of a solvent to obtain a mixture; and a mixture drying step of drying the mixture obtained in the mixing step.

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