Resin composition, fiber-reinforced resin composition, and molded article

Abstract

A resin composition containing a lignin component (A) and a thermoplastic resin (B), the lignin component (A) having an alcoholic hydroxyl group content of 1.5 mmol / g or less, the content of the lignin component (A) being 1-60 mass%, and the content of the thermoplastic resin (B) being 40-99 mass%.

Description

Technical Field

[0001] The present invention relates to a resin composition, a fiber-reinforced resin composition, and a molded article.

[0002] Specifically, the present invention relates to a resin composition, a fiber-reinforced resin composition, and a molded article having excellent moldability and mechanical properties. Background Art

[0003] In recent years, materials have been required to be applied to carbon neutrality worldwide, and resins are no exception.

[0004] As thermoplastic resins as biobased matrices, poly(lactic acid) (PLA), poly(butylene succinate) (PBS), PBAT (poly(butylene adipate-co-butylene terephthalate)), polyamide 610 (PA610), polyamide 11 (PA11), etc. are known. However, due to insufficient physical properties or high cost, they have not been fully popularized.

[0005] On the other hand, lignin is known as a biomass raw material derived from plants. Patent Document 1 discloses a resin composition containing a thermoplastic resin and lignin, and the thermoplastic resin is compatible with the lignin.

[0006] Prior Art Documents

[0007] Patent Documents

[0008] Patent Document 1: JP-A-2010-163481 Summary of the Invention

[0009] However, it has been found that the technology of Patent Document 1 still has room for further improvement from the viewpoints of improving the moldability and mechanical properties of the resin composition.

[0010] One object of the present invention is to provide a resin composition, a fiber-reinforced resin composition, and a molded article having excellent moldability and mechanical properties.

[0011] The present inventors have conducted intensive studies and as a result, have found that a resin composition containing a specific lignin component and a thermoplastic resin in a specific ratio has excellent moldability and mechanical properties, and thus have completed the present invention.

[0012] According to the present invention, the following resin compositions, etc. can be provided.

[0013] 1. A resin composition comprising a lignin component (A) and a thermoplastic resin (B), wherein the content of alcoholic hydroxyl groups in the lignin component (A) is 1.5 mmol / g or less,

[0014] the content of the lignin component (A) is 1 to 60% by mass,

[0015] The content of the aforementioned thermoplastic resin (B) is 40 to 99% by mass.

[0016] 2. The resin composition according to 1, wherein the total content of the alcoholic hydroxyl groups and carboxyl groups in the aforementioned lignin component (A) is 1.6 mmol / g or less.

[0017] 3. The resin composition according to 1 or 2, wherein the content of phenolic hydroxyl groups in the aforementioned lignin component (A) is 2.5 mmol / g or more, and the ratio of the content of phenolic hydroxyl groups to the content of alcoholic hydroxyl groups (content of phenolic hydroxyl groups / content of alcoholic hydroxyl groups) is 2.5 or more.

[0018] 4. The resin composition according to any one of 1 to 3, wherein the weight average molecular weight (Mw) of the aforementioned lignin component (A) is 1,000 to 3,500.

[0019] 5. The resin composition according to any one of 1 to 4, wherein the softening point of the aforementioned lignin component (A) is 100°C or higher and lower than 250°C.

[0020] 6. The resin composition according to any one of 1 to 5, wherein the aforementioned lignin component (A) contains two or more compounds represented by the following formula (1), and the proportion of the total amount of the compounds represented by the formula (1) relative to the total amount of the aforementioned lignin component (A) is 0.06% by mass or more.

[0021] [Chemical formula 1]

[0022]

[0023] (In the formula, * is bonded to the carbon atom on the ring substituted with any one of R 11 ~R 15 ; ** is bonded to the carbon atom on the ring substituted with any one of R 16 ~R 20 . R a is a hydrogen atom, a methyl group, an ethyl group, a furyl group, a hydroxymethylfuryl group, a hydroxyphenyl group, a hydroxymethoxyphenyl group or a hydroxydimethoxyphenyl group. R c1 , R c2 each independently represents a hydroxyl group, an alkoxy group, an amino group or a thiol group. R 11 ~R 20 not bonded to * or ** each independently represents a hydrogen atom, a hydroxyl group, a hydrocarbon group having 1 to 15 carbon atoms, a hydrocarbon ether group having 1 to 15 carbon atoms, or a group containing a carbonyl group. R 11 ~R 20 are optionally the same or different from each other. Among them, R 11 ~R 15At least one of them is a hydrogen atom, R 16 ~R 20 At least one of them is a hydrogen atom.)

[0024] 7. The resin composition according to any one of 1 to 6, wherein the maximum value of the peak of the differential distribution value (dw / dLogM) existing at a molecular weight LogM of 2.35 to 2.60 of the aforementioned lignin component (A) measured by gel permeation chromatography (GPC) is 50 or more and 150 or less, or the difference in the integral distribution value (%) at a molecular weight LogM of 2.35 to 2.55 is 5 or more and 15 or less.)

[0025] 8. The resin composition according to any one of 1 to 7, wherein the aforementioned thermoplastic resin (B) contains a polycondensation polymer.)

[0026] 9. The resin composition according to any one of 1 to 8, wherein the aforementioned thermoplastic resin (B) contains one or more selected from polyamide resins, polyester resins, and polycarbonate resins.)

[0027] 10. A fiber-reinforced resin composition comprising the resin composition according to any one of 1 to 9 and a reinforcing fiber (D).

[0028] 11. The fiber-reinforced resin composition according to 10, wherein the aforementioned reinforcing fiber (D) contains one or more selected from carbon fibers, glass fibers, aramid fibers, and cellulose fibers.)

[0029] 12. A molded article comprising the resin composition according to any one of 1 to 9, or the fiber-reinforced resin composition according to 10 or 11.)

[0030] 13. The molded article according to 12, which is an injection molded article.)

[0031] 14. The molded article according to 12, which is an extrusion molded article.)

[0032] 15. The molded article according to 12, which is a compression molded article.)

[0033] According to the present invention, a resin composition, a fiber-reinforced resin composition, and a molded article excellent in molding processability and mechanical properties can be provided.) Detailed Description of the Invention

[0034] Hereinafter, the resin composition, the fiber-reinforced resin composition, and the molded article of the present invention will be described in detail.)

[0035] In addition, in this specification, "x to y" represents a numerical range of "x or more and y or less". The upper limit value and the lower limit value described for the numerical range can be arbitrarily combined.)

[0036] 1. Resin composition (C)

[0037] The resin composition (C) according to one embodiment of the present invention contains a lignin component (A) and a thermoplastic resin (B), and the content of alcoholic hydroxyl groups in the lignin component (A) is 1.5 mmol / g or less.

[0038] The content of the aforementioned lignin component (A) is 1 to 60% by mass.

[0039] The content of the aforementioned thermoplastic resin (B) is 40 to 99% by mass.

[0040] According to the resin composition (C) of the present embodiment, effects of excellent moldability and mechanical properties can be obtained.

[0041] The reason for obtaining such effects is not necessarily clear, and it is speculated to be the interaction (chemical reaction) between the polar functional groups of the lignin component (A) and the thermoplastic resin (B), etc.

[0042] The resin composition disclosed in the above Patent Document 1 does not satisfy the conditions of the present invention due to the different structure of the lignin component (A).

[0043] In addition, the content of each of the alcoholic hydroxyl groups, phenolic hydroxyl groups, and carboxyl groups described later in the lignin component (A) is a value measured by the method described in the examples.

[0044] (Lignin component (A))

[0045] As described later, the lignin component (A) can be, for example, an extract (extracted lignin) obtained by extracting and refining from a lignin-containing material using a solvent containing an organic solvent. Typically, the lignin component (A) has lignin as the main component. For example, the content of lignin can be 90% by mass or more, 95% by mass or more, or 99% by mass or more.

[0046] The lignin component (A) contains at least lignin and may also contain other components. The other components can be components derived from the above extraction operation. Specifically, compounds represented by the following formula (1), compounds represented by the following formula (2), and free phenol monomers can be listed. The lignin component (A) can contain one or more of the other components (compounds represented by the following formula (1), compounds represented by the following formula (2), and free phenol monomers) listed here, or may not contain these other components. Typically, components other than lignin and the other components (compounds represented by the following formula (1), compounds represented by the following formula (2), and free phenol monomers) listed here do not conform to the lignin component (A). Among them, the case where the resin composition (C) contains components that do not conform to the lignin component (A) and the lignin component (A) at the same time is not excluded.

[0047] In one embodiment, the content of alcoholic hydroxyl groups in the lignin component (A) is 1.5 mmol / g or less, 1.3 mmol / g or less, or 1.0 mmol / g or less.

[0048] In one embodiment, the total content of alcoholic hydroxyl groups and carboxyl groups in the lignin component (A) is 1.6 mmol / g or less, 1.3 mmol / g or less, or 1.0 mmol / g or less. Thereby, excellent processing stability can be exhibited.

[0049] In one embodiment, the content of phenolic hydroxyl groups in the lignin component (A) is 2.5 mmol / g or more, 3.0 mmol / g or more, or 3.5 mmol / g or more, and the ratio of the content of phenolic hydroxyl groups to the content of alcoholic hydroxyl groups (content of phenolic hydroxyl groups / content of alcoholic hydroxyl groups) is 2.5 or more, 3.0 or more, or 3.5 or more. Thereby, moldability and mechanical properties can be balanced.

[0050] There is no particular limitation on the upper limit of the content of phenolic hydroxyl groups, for example, it is 10 mmol / g or less.

[0051] There is no particular limitation on the upper limit of the ratio of the content of phenolic hydroxyl groups to the content of alcoholic hydroxyl groups, for example, it is 20 or less.

[0052] In one embodiment, the weight-average molecular weight (Mw) of the lignin component (A) is 1,000 to 3,500. Mw can be 1,200 or more, and can be 1,500 or more. In addition, Mw can be 3,000 or less, can be 2,800 or less, can be 2,500 or less, can be 2,200 or less. In addition, in one embodiment, the weight-average molecular weight (Mw) of the lignin component (A) is 1,000 to 3,500, 1,000 to 3,000, 1,200 to 2,800, 1,500 to 2,500, or 1,500 to 2,200. Thereby, more excellent moldability can be exhibited.

[0053] In one embodiment, the molecular weight distribution (Mw / Mn) of the lignin component (A) is 2.2 to 3.5. Mw / Mn can be 2.3 or more, can be 2.4 or more, can be 2.5 or more, can be 2.6 or more. In addition, Mw / Mn can be 3.3 or less, can be 3.0 or less, can be 2.7 or less.

[0054] Each molecular weight of the lignin component (A) is measured by GPC using the same method as the method described in the examples below.

[0055] In one embodiment, the softening point of the lignin component (A) is 100°C or higher and lower than 250°C, 100°C or higher and lower than 220°C, 100°C or higher and lower than 200°C, 100°C or higher and lower than 180°C, 100°C or higher and lower than 165°C, 110°C or higher and lower than 165°C, or 110°C or higher and 150°C or lower. Thereby, excellent moldability can be exhibited.

[0056] In one embodiment, the lignin component (A) contains two or more compounds represented by the following formula (1) (sometimes referred to as "phenol dimers"), and the proportion of the total amount of the compounds represented by the formula (1) relative to the total amount of the lignin component (A) is 0.06% by mass or more.

[0057] [Chemical formula 2]

[0058]

[0059] (In the formula, * is bonded to a carbon atom on the ring substituted with any one of R 11 ~R 15 ; ** is bonded to a carbon atom on the ring substituted with any one of R 16 ~R 20 . R a is a hydrogen atom, a methyl group, an ethyl group, a furyl group, a hydroxymethylfuryl group, a hydroxyphenyl group, a hydroxymethoxyphenyl group, or a hydroxydimethoxyphenyl group. R c1 , R c2 each independently represents a hydroxyl group, an alkoxy group, an amino group, or a mercapto group. R 11 ~R 20 not bonded to * or ** each independently represents a hydrogen atom, a hydroxyl group, a hydrocarbon group having 1 to 15 carbon atoms, a hydrocarbon ether group having 1 to 15 carbon atoms, or a group containing a carbonyl group. R 11 ~R 20 may be the same or different from each other optionally. Among them, at least one of R 11 ~R 15 is a hydrogen atom, and at least one of R 16 ~R 20 is a hydrogen atom.)

[0060] In formula (1), each line extending from the C bonded to R a to the left and right rings is bonded to a carbon atom on the ring substituted with any one of R 11 ~R 15 and a carbon atom on the ring substituted with any one of R 16 ~R 20 , and two of R 11 ~R 20 bonded to the carbon atoms on the ring to which the aforementioned lines are bonded form a single bond with the aforementioned lines.

[0061] The hydrocarbon group having 1 to 15 carbon atoms may be linear or branched, and these hydrocarbon groups may be saturated or unsaturated. The hydrocarbon group having 1 to 15 carbon atoms is preferably a linear alkyl group or a branched hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear hydrocarbon group or a branched hydrocarbon group having 1 to 5 carbon atoms, and further preferably a linear hydrocarbon group having 1 to 3 carbon atoms.

[0062] All of these suitable hydrocarbon groups may be saturated or unsaturated.

[0063] The hydrocarbon ether group having 1 to 15 carbon atoms may be linear or branched, and these hydrocarbons may be saturated or unsaturated.

[0064] The hydrocarbon ether group having 1 to 15 carbon atoms is preferably a linear hydrocarbon ether group or a branched hydrocarbon ether group having 1 to 10 carbon atoms, more preferably a linear hydrocarbon ether group or a branched hydrocarbon ether group having 1 to 5 carbon atoms, and further preferably a linear hydrocarbon ether group having 1 to 3 carbon atoms.

[0065] The hydrocarbons of all of these suitable hydrocarbon ether groups may be saturated or unsaturated.

[0066] It should be noted that the hydrocarbon ether group can be represented by, for example, -(CH2) a -O-(CH2) b -H (a and b are both integers of 1 or more. Among them, a + b is 2 or more). In this case, when the hydrocarbon ether group is linear, it means that the structures represented by -(CH2) a - and -(CH2) b - are both linear, and when the hydrocarbon ether group is branched, it means that any one of the structures represented by -(CH2) a - or -(CH2) b - is branched.

[0067] In addition, when the hydrocarbon of the hydrocarbon ether group is saturated, it means that -(CH2) a - and -(CH2) b - are both saturated hydrocarbons, and when the hydrocarbon of the hydrocarbon ether group is unsaturated, it means that any one of -(CH2) a - or -(CH2) b - is an unsaturated hydrocarbon.

[0068] In addition, when the hydrocarbon ether group is represented by -(CH2) a -O-(CH2) b -, the number of carbon atoms of the hydrocarbon ether group is the number indicated by (a + b).

[0069] Examples of the group containing a carbonyl group include an aldehyde group (-CHO), a carboxyl group (-COOH), a carbonyl group (-COR), an ester group (-COOR), and an amide group (-CONRR').

[0070] R c1 、R c2 may be any one of a hydroxyl group, an alkoxy group, an amino group or a mercapto group, preferably a hydroxyl group or an alkoxy group, more preferably a hydroxyl group.

[0071] The proportion of the total amount of the compound represented by the formula (1) relative to the total amount of the lignin component (A) is 0.06% by mass or more, may be 0.1% by mass or more, may be 0.3% by mass or more, may be 0.5% by mass or more, may be 0.7% by mass or more. Thus, the compatibility between the lignin component (A) and the thermoplastic resin (B) can be improved, and the mechanical properties of the resin composition (C) can be further improved.

[0072] The upper limit value of the proportion of the total amount of the compound represented by the formula (1) relative to the total amount of the lignin component (A) is not particularly limited, and typically, it is 10% by mass or less.

[0073] The amount of lignin contained in the resin composition (C) or the lignin component (A) can be confirmed as follows: According to the method for measuring methoxy groups based on the Viebock and Schwappach method (refer to "Research Methods of Lignin Chemistry", P336 - 340, published by Yuni in 1994), measure the amount of methoxy groups contained in the resin composition (C), and substitute the measured value of the amount of methoxy groups obtained as the amount of lignin, and confirm it in the form of the value calculated therefrom.

[0074] The types and contents of the compounds represented by the formula (1) contained in the resin composition (C) or the lignin component (A) are confirmed by liquid chromatography - mass spectrometry (LC / MS).

[0075] In LC / MS, as the compounds represented by the formula (1), it is assumed that they contain the following compounds (a) - (h). For example, when the content of the target compound is less than 0.01% by mass, the target compound is regarded as below the detection limit. The details of the measurement are described in the examples.

[0076] It should be noted that the content of each of the compounds (a) - (h) determined by the aforementioned LC / MS also includes the content of isomers having the same molecular weight as each compound but different bonding positions.

[0077] [Chemical formula 3]

[0078]

[0079]

[0080] In one embodiment, the lignin component (A) contains two or more compounds represented by any one of the formulas (a) to (h), and the proportion of the total amount of the compounds represented by any one of the formulas (a) to (h) relative to the total amount of the lignin component (A) is 0.06% by mass or more, may be 0.1% by mass or more, may be 0.3% by mass or more, may be 0.5% by mass or more, may be 0.7% by mass or more.

[0081] In one embodiment, the content of the compound represented by the following formula (2) (also referred to as compound (2)) is 0.1% by mass or less, may be 0.05% by mass or less, with respect to the entire resin composition (C). In addition, the compound represented by formula (2) is regarded as conforming to the lignin component (A).

[0082] [Chemical formula 4]

[0083]

[0084] By making the content of the compound represented by formula (2) within the above range, excellent mechanical properties can be exhibited.

[0085] The content of the compound represented by formula (2) is measured by the method described in the examples below.

[0086] In one embodiment, the content of the free phenol monomer is 0.02% by mass or more and 8.0% by mass or less with respect to the entire resin composition (C). The free phenol monomer contained in the resin composition (C) is mainly the monomer remaining after a part of the phenol used in the production of the lignin component is not removed. The content of the free phenol monomer may be 0.1% by mass or more, may be 0.5% by mass or more, may be 1.0% by mass or more, may be 2.0% by mass or more, may be 3.0% by mass or more. In addition, the free phenol monomer is regarded as conforming to the lignin component (A).

[0087] The content of the free phenol monomer is measured by the method described in the examples below.

[0088] In one embodiment, the maximum value of the differential distribution value (dw / dLogM) peak existing at a molecular weight LogM of 2.35 to 2.60, measured by gel permeation chromatography (GPC), for the lignin component (A) is 50 or more and 150 or less, or the difference in the integral distribution value (%) at a molecular weight LogM of 2.35 to 2.55 is 5 or more and 15 or less.

[0089] By making the maximum value of the peak of the differential distribution value (dw / dLogM) existing at a molecular weight LogM of the lignin component measured by GPC of 2.35 to 2.60 be 50 or more and 150 or less, the compatibility of the lignin component (A) and the thermoplastic resin (B) can be improved, and the mechanical properties of the resin composition (C) can be further improved. The above maximum value can be 130 or less, and can be 110 or less.

[0090] Similarly, by making the difference in the integral distribution value (%) at a molecular weight LogM of 2.35 to 2.55 be 5 or more and 15 or less, the compatibility of the lignin component (A) and the thermoplastic resin (B) can be improved, and the mechanical properties of the resin composition (C) can be further improved. The above integral distribution value can be 6 or more, can be 7 or more, can be 8 or more. In addition, it can be 13 or less, can be 12 or less.

[0091] As described above, the lignin component (A) is obtained, for example, by extraction from a lignin-containing material using a solvent containing an organic solvent, or by reacting a lignin-containing material with a solvent containing an organic solvent and then performing purification. Typically, the solvent containing an organic solvent contains at least the compound represented by the following formula (I).

[0092] [Chemical formula 5]

[0093]

[0094] In the above formula (I), R 31 ~R 35 each independently represents a hydrogen atom, a hydroxyl group, a hydrocarbon group having 1 to 15 carbon atoms, a hydrocarbon ether group having 1 to 15 carbon atoms, or a group containing a carbonyl group, and R 31 ~R 35 are optionally the same or different. Among them, at least one of R 31 ~R 35 is a hydrogen atom.

[0095] As the hydrocarbon group when R 31 ~R 35 is a hydrocarbon group having 1 to 15 carbon atoms, it is the same as R 11 ~R 20 in the foregoing formula (1). In addition, as the hydrocarbon ether group when R 31 ~R 35 is a hydrocarbon ether group having 1 to 15 carbon atoms, it is the same as R 11 ~R 20 in the foregoing formula (1). In addition, as the group containing a carbonyl group when R 31 ~R 35 is a group containing a carbonyl group, it is the same as R 11 ~R20 Same

[0096] R c represents a hydroxyl group, an alkoxy group, an amino group, or a thiol group.

[0097] R c can be any one of a hydroxyl group, an alkoxy group, an amino group, or a thiol group, and is preferably a hydroxyl group or an alkoxy group, more preferably a hydroxyl group, from the viewpoint of affinity with the basic skeleton of lignin.

[0098] The solvent may contain compounds other than the compound represented by the above formula (I). As the solvent component other than the compound represented by the above formula (I), from the viewpoints of solubility of lignin in the raw material and economy, one or more of alcohols, ketones, ethers, esters, aromatics other than the compound represented by formula (I), and water can be cited.

[0099] In this specification, "lignin" refers to a high molecular compound formed by polymerization of three lignin monomers of p-hydroxycinnamols, which has a basic skeleton represented by the following formula (A).

[0100] [Chemical formula 6]

[0101]

[0102] In the above formula (A), as the substituent R 3 and R 4 represent a hydrogen atom or a methoxy group. The group in which both R 3 and R 4 are hydrogen atoms is called a p-hydroxyphenyl nucleus (H-type skeleton), and the group in which any one of R 3 and R 4 is a hydrogen atom is called a guaiacyl nucleus (G-type skeleton), and the group in which neither R 3 nor R 4 is a hydrogen atom is called a syringyl nucleus (S-type skeleton).

[0103] It should be noted that X in the above formula (A) represents bonding to a carbon atom, and Y represents bonding to a hydrogen atom or a carbon atom.

[0104] The lignin-containing material (raw material) used as the extraction target of the lignin component (A) or the above reaction target is not particularly limited as long as it is a lignin-containing material.

[0105] In one embodiment, the lignin-containing material is one or more selected from biomass and biomass residues.

[0106] As the biomass residue, for example, biomass residues derived from plant-based biomass such as woody biomass and herbaceous biomass can be cited.

[0107] For example, as biomass residues, saccharification residues and fermentation residues of plant-based biomass (second-generation ethanol saccharification residues, second-generation ethanol fermentation residues, etc.), black liquor, and lignin refined from black liquor (sulfide lignin, sulfate lignin, alkali lignin, etc.), organic solvent lignin extracted from plant-based biomass using organic solvents, etc. can be cited, and any one or more of these can be used. Among these, from the viewpoints of ease of acquisition, quality of the lignin component, and economy, as the lignin-containing material, it is preferable to use any one or more of the saccharification residues and fermentation residues of plant-based biomass, and organic solvent lignin.

[0108] Woody biomass and herbaceous biomass can be non-edible plant biomass, and can also be lignocellulosic biomass.

[0109] Examples of woody biomass include coniferous trees and broad-leaved trees such as cedar, Japanese cypress, hinoki cypress, cherry tree, eucalyptus, beech, bamboo, etc.

[0110] Examples of herbaceous biomass include, for example, the trunk and empty fruit bunches of oil palm, the fibers and seeds of oil palm fruits, oil palm shells, bagasse (the press residue of sugarcane and high-biomass sugarcane), sugarcane tops (the tops and leaves of sugarcane), energy sugarcane, rice straw, wheat straw, the cob, stem, leaves, and residues of corn (corn stover, corn cob, corn husk), residues of sorghum (including sweet sorghum), the bark and shells of Jatropha curcas, cashew nut shells, switchgrass, Erianthus arundinaceus, high-biomass yield crops, energy crops, etc.

[0111] Among these, herbaceous biomass is preferable, and more preferably the empty fruit bunches of oil palm, the fibers and seeds of oil palm fruits, oil palm shells, wheat straw, the cob, stem, leaves, and residues of corn (corn stover, corn cob, corn husk), bagasse, residues of sorghum (including sweet sorghum), sugarcane tops, energy sugarcane, and the residues after extracting these useful components. More preferably, the empty fruit bunches of oil palm, oil palm shells, the cob, stem, leaves, and residues of corn (corn stover, corn cob, corn husk), bagasse, residues of sorghum (including sweet sorghum), sugarcane tops, energy sugarcane, and the residues after extracting these useful components. It should be noted that the above-mentioned useful components include, for example, hemicellulose, saccharides, minerals, water, etc.

[0112] Bagasse contains about 5 to 30% by mass of lignin. In addition, the lignin in bagasse contains all of H nucleus, G nucleus, and S nucleus as the basic skeleton.

[0113] Plant-based biomass can also be used in the form of crushed products. In addition, it can be in any form such as blocks, small pieces, powders, or hydrates containing water.

[0114] The empty fruit bunches, oil palm shells, bagasse, corn cobs, etc. of oil palm are treated by methods such as organic solvent method, pressurized hot water method, steam explosion method, ammonia treatment method, ammonia explosion method, acid treatment method, dilute sulfuric acid explosion method, alkali treatment method, oxidative decomposition method, thermal decomposition and microwave heating method, etc. Acid treatment, dilute sulfuric acid explosion, steam explosion, etc. are preferably carried out. After separating the hemicellulose to the solution side, the cellulose is made into glucose by enzymes, which is also separated to the solution side, or directly saccharified with the cellulose without separating the hemicellulose and separated to the solution side. The remaining solid is the saccharification residue of plant-based biomass. Or, without separating the sugars, it is separated to the solution side in the form of ethanol by fermentation, and the remaining solid is the fermentation residue of plant-based biomass.

[0115] The saccharification residue of plant-based biomass has lignin as the main component and contains decomposed organic matter, catalyst, enzyme, ash, cellulose, etc. In addition, the fermentation residue of plant-based biomass has lignin as the main component and contains decomposed organic matter, catalyst, enzyme, yeast, ash, cellulose, etc.

[0116] The manufacturing method of the lignin component (A) is as follows, for example.

[0117] Using any one or more of the saccharification residue and fermentation residue of plant-based biomass as raw materials, a solvent containing a compound having at least one selected from, for example, hydroxyl group and ether bond (hereinafter also referred to as "organic solvent A") is added. The organic solvent A will be described in detail in the "solvent" section below.

[0118] The solvent containing the organic solvent A typically contains at least the compound represented by the aforementioned formula (I).

[0119] After adding the solvent and continuing to heat for about 2 to 4 hours, since the heating solution contains insoluble matter, it is filtered using a No. 2 filter paper. The filtered solid is the unextracted component and inorganic inclusions. The filtrate is distilled under reduced pressure to remove the solvent. The solvent that is not completely removed by distillation is removed by vacuum drying. The separated solid is the lignin component (A).

[0120] In addition, as the lignin-containing material used as a raw material, lignin separated from non-edible plant biomass through treatments such as the organic solvent method, pressurized hot water method, steam explosion method, ammonia treatment method, ammonia explosion method, acid treatment method, dilute sulfuric acid explosion method, alkali treatment method, oxidative decomposition method, thermal decomposition, and microwave heating method can also be used. Specifically, lignin obtained through the following operations can also be used: for example, by treating with an organic solvent or a solvent containing an organic solvent and water, the lignin contained in the non-edible plant biomass is dissolved into the solvent, and after filtering the lignin-containing solution to remove cellulose and the like, the solution is concentrated and dried to separate the lignin. It should be noted that by using a solvent containing organic solvent A as the above-mentioned organic solvent, the lignin component (A) can also be directly extracted from the non-edible plant biomass.

[0121] (Solvent)

[0122] The solvent used in the extraction or reaction contains an organic solvent. The solvent containing an organic solvent typically contains the compound represented by the above formula (I) as described above. Examples of organic solvents other than the compound represented by the above formula (I) include alcohols such as methanol, ethanol, isopropanol, ethylene glycol, and polyethylene glycol; ketones such as acetone and methyl ethyl ketone; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate; and aromatic compounds other than the compound represented by formula (I) such as toluene.

[0123] In one embodiment, a solvent containing organic solvent A (a compound having at least one selected from a hydroxyl group and an ether bond) is used in the extraction or reaction of lignin. By using organic solvent A as the organic solvent for extracting lignin or causing it to react, it is expected to suitably prevent the extract or reactant derived from the lignin from being modified into a hydrophilic substance. It should be noted that the extracted lignin component (A) can react with the organic solvent containing organic solvent A. By using organic solvent A, an extract or reactant derived from lignin can be suitably generated.

[0124] When organic solvent A has a hydroxyl group, the number of hydroxyl groups in organic solvent A is not particularly limited. For example, it can be 1 or more, and can also be 10 or less, 5 or less, 4 or less, 3 or less, 2 or less. The number of hydroxyl groups in organic solvent A can be 1, 2, 3, 4, or 5, can be 1, 2, or 3, can be 1 or 2, and can be 1.

[0125] Examples of the organic solvent A having two hydroxyl groups include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, diethylene glycol, triethylene glycol, polyethylene glycol, etc. In addition, examples of the organic solvent A having three hydroxyl groups include glycerol, 1,2,3-butanetriol, 1,2,4-butanetriol, 1,2,3-heptanetriol, 1,2,4-heptanetriol, 1,2,5-heptanetriol, 2,3,4-heptanetriol, etc. Examples of the organic solvent A having four hydroxyl groups include pentaerythritol, erythritol, etc. Examples of the organic solvent A having five hydroxyl groups include xylitol, etc. Examples of the organic solvent A having six hydroxyl groups include sorbitol, etc.

[0126] As these organic solvents A having two or more hydroxyl groups (organic solvents A having multiple hydroxyl groups), from the viewpoints of improving the extraction or reaction efficiency of lignin and economy, it is preferably one or more selected from ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, and glycerol, more preferably one or more selected from ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol, polypropylene glycol, and glycerol, further preferably one or more selected from ethylene glycol, polyethylene glycol, and glycerol, and still further preferably ethylene glycol and polyethylene glycol.

[0127] The organic solvent A is preferably a compound represented by the following formula (II).

[0128] R-OH (II)

[0129] (In the formula (II), R is an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group.)

[0130] When R is an alkyl group having 1 to 10 carbon atoms, the number of carbon atoms of the alkyl group can be 1 or more, 2 or more, 3 or more, or 4 or more, and further, can be 10 or less, 8 or less, 6 or less. The alkyl group can be linear or branched.

[0131] In particular, by setting the number of carbon atoms of the alkyl group to 2 or more, it is possible to more significantly prevent the extract or reactant derived from lignin from being modified into a hydrophilic substance. In addition, the larger the number of carbon atoms is, such as 2 or more, 3 or more, and further 4 or more, the more significantly this effect can be expected to be exerted.

[0132] The compound represented by the formula (II) wherein R is an alkyl group having 1 to 10 carbon atoms is, for example, one or more selected from methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutanol, tert-butanol, 1-pentanol, 2-pentanol, 3-methyl-1-butanol, 1-hexanol, cyclohexanol, 1-heptanol, 1-octanol, 2-ethylhexanol, etc., preferably one or more selected from methanol, ethanol, 1-propanol and 2-propanol, more preferably one or more selected from methanol, ethanol and 2-propanol, and further preferably ethanol.

[0133] The compound represented by the formula (I) is equivalent to the case where R in the formula (II) is a substituted or unsubstituted phenyl group and the hydroxyl group (the "OH" group in the formula (II)) is the aforementioned R. c Case.

[0134] The preferred compound represented by the formula (I) is such that at least one of 31 R, 33 R, 35 and 31 R 33 is a hydrogen atom, and more preferably 35 all of R, R and R are hydrogen atoms.

[0135] Examples of the compound represented by the formula (I) include 2-alkylphenols such as phenol, catechol, resorcinol, hydroquinone, phloroglucinol, o-cresol, m-cresol, p-cresol, 2-ethylphenol and 2-propylphenol; 3-alkylphenols such as 3-ethylphenol, 3-propylphenol and cardanol; 4-alkylphenols such as 4-ethylphenol, 4-propylphenol, 4-octylphenol and 4-nonylphenol; 5-alkylresorcinols such as 5-methylresorcinol, 5-ethylresorcinol and 5-propylresorcinol; 3,5-dialkylphenols such as 3,5-dimethylphenol, 3-methyl-5-ethylphenol and 3,5-diethylphenol; anisole, aniline, thiophenol, etc. One or more, preferably one or more selected from phenol, catechol, resorcinol, hydroquinone, o-cresol, m-cresol, p-cresol, cardanol, 4-octylphenol, 4-nonylphenol, anisole, more preferably one or more selected from phenol, catechol, resorcinol, hydroquinone, o-cresol, m-cresol, p-cresol, anisole, further preferably one or more selected from phenol, o-cresol, m-cresol, p-cresol, anisole, further preferably one or more selected from phenol, anisole, and further preferably phenol.

[0136] When using a compound represented by the formula (I) such as phenol as an organic solvent, by reacting the lignin component with the compound represented by the formula (I), an increase in the H-type skeleton and the G-type skeleton can be expected.

[0137] When using the compound represented by the formula (I) as an organic solvent, by reacting lignin with the compound represented by the formula (I), it is expected that the substituents R in the lignin basic skeleton represented by the formula (A) in lignin 3 and R 4 undergo a substitution reaction to be transformed into a structure derived from the compound represented by the formula (I), and a compound represented by the formula (1) is generated.

[0138] As the organic solvent A, one kind or two or more kinds in combination can be used.

[0139] As the organic solvent A, for example, one kind or two or more kinds selected from the compounds represented by the formula (II) in which R is an alkyl group having 1 to 10 carbon atoms and one kind or two or more kinds selected from the compounds represented by the formula (II) in which R is a substituted or unsubstituted phenyl group (i.e., the compound represented by the formula (I)) can be used in combination. If specific examples are listed, ethanol and phenol can be used in combination.

[0140] The organic solvent may contain other organic solvents in addition to the organic solvent A.

[0141] There is no particular limitation on the other organic solvents, and examples thereof include ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate, and aromatic compounds other than the compound represented by the formula (I) such as toluene. One kind or two or more kinds in combination of the other organic solvents can be used.

[0142] In one embodiment, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 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, or 99% by mass or more of the organic solvent is the organic solvent A.

[0143] The solvent used in the extraction or reaction may contain water in addition to the organic solvent.

[0144] Regarding the ratio of water to the organic solvent in the solvent used in the extraction or reaction, for example, relative to 100 parts by mass of the organic solvent, it can be 10 parts by mass or more, 20 parts by mass or more, 30 parts by mass or more, 50 parts by mass or more, or 70 parts by mass or more, and in addition, it can be 900 parts by mass or less, 700 parts by mass or less, 400 parts by mass or less, 300 parts by mass or less, or 100 parts by mass or less.

[0145] When extracting the lignin component (A) from a lignin-containing material using a solvent, or when reacting a lignin-containing material with a solvent, the solvent may or may not phase-separate. In the case where the solvent phase-separates, the "solvent used in the extraction or reaction" refers to the solvent that constitutes the phase containing the lignin component (A) at the highest concentration.

[0146] (Extraction)

[0147] The extraction in the present invention means: extracting the lignin component (A) containing an extract derived from lignin from a lignin-containing material containing components other than lignin.

[0148] "Extraction" in one embodiment means: when the lignin-containing material is a lignin-containing solid, extracting the lignin component (A) from the lignin-containing solid, rather than an operation of adding an organic solvent to a solution in which all lignin has been dissolved (such as an aqueous solution containing an alkaline compound). In this embodiment, the lignin-containing material before extraction (the lignin-containing material before adding the organic solvent) contains:

[0149] a lignin-containing solid and lignin already dissolved in a solvent; or

[0150] contains a lignin-containing solid but does not contain lignin already dissolved in a solvent.

[0151] When extracting, there is no particular limitation on the addition amount of the solvent added to the lignin-containing material.

[0152] The mass ratio of the solvent to the lignin in the lignin-containing material [solvent / lignin] can be, for example, 0.1 or more, and can also be 15 or less, 10 or less, 5 or less, 4 or less, 3 or less, 2 or less, 1 or less, 0.7 or less, or 0.5 or less.

[0153] (Reaction)

[0154] In this specification, typically, reacting a lignin-containing material with a solvent means: reacting a lignin-containing material extracted from plant-based biomass with a solvent to obtain the lignin component (A).

[0155] In one embodiment, the above "reaction" means: reacting a lignin-containing material refined from black liquor or a lignin-containing material extracted from plant-based biomass using an organic solvent with a solvent to obtain the lignin component (A).

[0156] When reacting, there is no particular limitation on the addition amount of the solvent added to the lignin-containing material.

[0157] The mass ratio of the solvent to the lignin in the lignin-containing material [solvent / lignin] can be, for example, 0.1 or more, and can also be 15 or less, 10 or less, 5 or less, 4 or less, 3 or less, 2 or less, 1 or less, 0.7 or less, or 0.5 or less.

[0158] (Acid catalyst)

[0159] The above extraction or reaction can be carried out in the absence or presence of a catalyst. Examples of the catalyst include, for example, an acid catalyst. Examples of the acid catalyst include inorganic acids such as phosphoric acid, phosphate esters, hydrochloric acid, sulfuric acid, and sulfuric acid esters; organic acids such as acetic acid, formic acid, oxalic acid, and p-toluenesulfonic acid, etc. The acid catalyst can be used alone or in combination of two or more.

[0160] When the total amount of lignin and the solvent is set to 100 parts by mass, the acid catalyst can be, for example, more than 0 mass%, 0.1 mass% or more, or 0.2 mass% or more, and can also be 5.0 mass% or less, 3.0 mass% or less, or 2.6 mass% or less.

[0161] When the extraction or reaction is carried out under the condition of no catalyst, for example, the post-treatment (refining process) after the extraction or reaction process can be omitted.

[0162] The extraction or reaction temperature is not particularly limited as long as it can extract the lignin component (A) from the lignin-containing material or can cause the lignin-containing material to react with the solvent. For example, it can be 100 °C or more, 140 °C or more, more than 140 °C, 150 °C or more, or 180 °C or more, and can also be 350 °C or less, 300 °C or less, 270 °C or less, 250 °C or less, or 230 °C or less. If it exceeds 140 °C, the solubility of lignin (lignin component (A)) can be increased, and the extraction or reaction can be promoted. In addition, if it is 300 °C or less, the re-bonding or polymerization of lignin can be suitably prevented.

[0163] The extraction or reaction time can be set appropriately. For example, it can be 0.1 hour or more, 0.5 hour or more, 1 hour or more, or 2 hours or more, and can also be 15 hours or less, 10 hours or less, or 8 hours or less.

[0164] (Refining)

[0165] The lignin component (A) is produced by the above extraction or reaction, and can be refined after the extraction or reaction as needed. Hereinafter, an example of refining will be described.

[0166] As the purification (purification process), first, the extracted lignin component (A) can be subjected to a solid-liquid separation process. The extracted lignin component (A) is dissolved in a solvent, but the unextracted components and inorganic inclusions exist in the liquid in solid form. They are preferably removed by filtration (while hot). For example, the extract is poured into a pressure (while hot) filter equipped with filter paper such as No. 5C or No. 2, and pressure filtration is carried out at about 20 to 100 °C, about 20 to 70 °C, usually at about 20 to 50 °C and about 0.1 to 0.99 MPa, usually at about 0.1 to 0.4 MPa. The filter solid can be diluted and / or washed with an appropriate solvent and then filtered. In this filtration, the lignin component (A) is contained in the filtrate. Additionally, for example, the extraction product solution can be diluted and / or washed with any one or more of low-boiling general solvents such as water, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol, ethanol, and isopropyl alcohol, and ethers such as tetrahydrofuran, and then solid-liquid separation is carried out. In this solid-liquid separation, the lignin component (A) is contained in the solution.

[0167] The method for carrying out solid-liquid separation is not particularly limited, and examples include filtration, filter pressurization, centrifugation, dehydrators, etc.

[0168] Alternatively, the solution containing the above-mentioned lignin component (A) can be subjected to distillation. The distillation can be carried out by vacuum distillation at a temperature of about 40 to 200 °C, usually about 50 to 150 °C, and under a reduced pressure of about 3 to 20 kPa, usually 5 to 10 kPa, to remove the solvent. In this distillation, the lignin component (A) can be obtained in the form of a solid or a viscous solid. Additionally, for example, when using other dilution solvents, vacuum distillation can be carried out at an appropriate temperature considering the boiling point of the solvent to remove the low-boiling general solvent, and then, using the same method as above, the solvent used in the extraction is removed. In this distillation, the lignin component (A) is obtained in the form of a solid or a viscous solid.

[0169] The lignin component (A) obtained by distillation is usually heated to 50 to 200 °C and vacuum dried in a solid or molten state, whereby the residual solvent (such as organic solvent A) can be removed and purified. Additionally, by directly carrying out the same vacuum drying on the lignin component (A) that is in a flowing state after being heated after distillation, the residual solvent (such as organic solvent A) can be removed and purified.

[0170] The lignin component (A) obtained by distillation or vacuum dry solidification is preferably not reprecipitated. Thereby, it is possible to easily obtain a lignin component containing the compound represented by the aforementioned formula (1) within the above content range.

[0171] Alternatively, in the purification process, any one or a combination of two or more of the above-mentioned filtration, distillation, and vacuum dry solidification can be carried out.

[0172] The organic solvents remaining in the lignin component (A) are not particularly limited, and are usually less than 30% by mass, preferably less than 10% by mass, more preferably less than 5% by mass, and still more preferably less than 1% by mass, relative to their total amount.

[0173] By the production method of the lignin component (A) contained in the resin composition (C) of the present invention, among the contents of lignin contained in the saccharification residue of plant-based biomass and the fermentation residue of plant-based biomass, preferably 50% by mass or more is taken out in the form of the lignin component (A), more preferably 60% by mass or more is taken out in the form of the lignin component (A), still more preferably 70% by mass or more is taken out in the form of the lignin component (A), even more preferably 80% by mass or more is taken out in the form of the lignin component (A), and even more preferably 90% by mass or more is taken out in the form of the lignin component (A).

[0174] (Thermoplastic resin (B))

[0175] The thermoplastic resin (B) is not particularly limited, and various thermoplastic resins can be used.

[0176] Examples of the thermoplastic resin (B) include polyamide resins, acrylic resins, polyphenylene sulfide resins, polyvinyl chloride resins, polyolefins, polyacetal resins, polycarbonate resins, polyurethanes, polybutylene terephthalate, acrylonitrile-butadiene-styrene (ABS) resins, phenoxy resins, polysulfones, polyethersulfones, polyether ketones, polyetherether ketones, polyester resins, etc. Among them, polyamide is suitable.

[0177] As the polyamide resin, known polyamide resins can be used. Examples of the polyamide resin include polyamide-4, polyamide-4,6, polyamide-6, polyamide-6,6, polyamide-3,4, polyamide-12, polyamide-11, polyamide-4,10, polyamide-6,10 (also referred to as "polyamide-610 (PA610)"), polyamide-4T, polyamide-6T, polyamide-9T, polyamide-10T, and polyamides obtained from adipic acid and m-xylenediamine, etc. Among them, polyamide-6, polyamide-6,6, polyamide-6,10, polyamide-11, and polyamide-12 are suitable.

[0178] In one embodiment, the thermoplastic resin (B) contains a polycondensation polymer. The polycondensation polymer refers to a polymer obtained by a polycondensation reaction.

[0179] In one embodiment, the thermoplastic resin (B) contains one or more selected from polyamide resins, polyester resins, and polycarbonate resins.

[0180] By making the thermoplastic resin (B) contain a polycondensation-based polymer, particularly one or more selected from polyamide resins, polyester resins, and polycarbonate resins, the effect of improving mechanical properties achieved by the interaction between the lignin component (A) and the thermoplastic resin (B) is significantly exerted.

[0181] The thermoplastic resin (B) may contain a thermoplastic resin of a biological matrix. Examples of the thermoplastic resin of a biological matrix include, for example, polylactic acid (PLA), polybutylene succinate (PBS), PBAT (polybutylene adipate-butylene terephthalate), and the above-mentioned polyamide-610 (PA610), polyamide-11 (PA11), etc.

[0182] 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, 98% by mass or more, or substantially 100% by mass of the thermoplastic resin (B) is a polycondensation-based polymer, or one or more selected from polyamide resins, polyester resins, and polycarbonate resins.

[0183] In one embodiment, the content of the lignin component (A) in the resin composition (C) is 1 to 60% by mass, 5 to 50% by mass, or 10 to 45% by mass.

[0184] In one embodiment, the content of the thermoplastic resin (B) in the resin composition (C) is 40 to 99% by mass, 50 to 95% by mass, or 55 to 90% by mass.

[0185] The resin composition (C) may or may not contain other components in addition to the lignin component (A) and the thermoplastic resin (B). Examples of other components include, for example, antioxidants, crystal nucleating agents, mold release agents, etc. One or more of them can be arbitrarily selected from known substances and used.

[0186] Examples of the antioxidant include, for example, phosphorus-based antioxidants, phenolic antioxidants, amine-based antioxidants, sulfur-based antioxidants, etc. They can be used alone or in combination of multiple kinds.

[0187] Examples of the crystal nucleating agent include, for example, inorganic crystal nucleating agents and organic crystal nucleating agents. They can be used alone or in combination of multiple kinds.

[0188] Examples of the mold release agent include, for example, polyethylene wax, silicone oil, long-chain carboxylic acids, long-chain carboxylic acid metal salts, etc. They can be used alone or in combination of multiple kinds.

[0189] 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, 98% by mass or more, or substantially 100% by mass of the resin composition (C) is the lignin component (A) and the thermoplastic resin (B).

[0190] In one embodiment, in the resin composition (C), the proportion of the lignin component (A) relative to the total amount of the lignin component (A) and the thermoplastic resin (B) is 1 to 60% by mass, 5 to 50% by mass, or 10 to 45% by mass. Additionally, the proportion of the thermoplastic resin (B) is 40 to 99% by mass, 50 to 95% by mass, or 55 to 90% by mass.

[0191] 2. Fiber Reinforced Resin Composition (E)

[0192] The fiber reinforced resin composition (E) according to one embodiment of the present invention contains the resin composition (C) according to one embodiment of the present invention and the reinforcing fiber (D).

[0193] According to the fiber reinforced resin composition (E) of this embodiment, effects of excellent moldability and mechanical properties can be obtained.

[0194] (Reinforcing Fiber (D))

[0195] In one embodiment, the reinforcing fiber (D) contains one or more selected from carbon fiber, glass fiber, aramid fiber, and cellulose fiber. Thereby, the effects of the present invention are exhibited more favorably. Among these, carbon fiber and glass fiber are preferred, and carbon fiber is particularly preferred.

[0196] As the carbon fiber, various carbon fibers such as PAN - based using polyacrylonitrile as a raw material, pitch - based using coal tar pitch in petroleum or coal as a raw material, thermosetting resins, for example, phenol - based using phenolic resin as a raw material, etc. can be used. The carbon fiber can be obtained by a vapor - growth method or can be recycled carbon fiber (RCF). Thus, the carbon fiber is not particularly limited, and preferably at least one carbon fiber selected from PAN - based carbon fiber, pitch - based carbon fiber, thermosetting - based carbon fiber, phenol - based carbon fiber, vapor - grown carbon fiber, and recycled carbon fiber (RCF).

[0197] There are substances in which the graphitization degree of carbon fiber varies depending on the raw material quality and calcination temperature during manufacturing, and they can be used regardless of the graphitization degree. The shape of the carbon fiber is not particularly limited, and carbon fibers having at least one shape selected from ground fibers, chopped strand (chopped roving), short fiber form, roving, filament, tow, whisker, nanotube, etc. can be used. In the case of chopped strand (chopped roving), fibers with an average fiber length of 0.1 to 50 mm and an average fiber diameter of 5 to 20 μm are preferably used. The density of the carbon fiber is not particularly limited, and it is preferably 1.75 to 1.95 g / cm 3 .

[0198] The form of the carbon fiber can be single fibers or fiber bundles, and both single fibers and fiber bundles can be mixed. The number of single fibers when forming each fiber bundle can be substantially uniform in each fiber bundle, or can be different. The average fiber diameter of the carbon fiber varies depending on the form. For example, carbon fibers with an average fiber diameter preferably of 0.0004 to 15 μm, more preferably 3 to 15 μm, and even more preferably 5 to 10 μm can be used.

[0199] When the carbon fiber has the form of a fabric, non-woven fabric or unidirectional material, single fibers with an average fiber diameter preferably of 3 to 15 μm, more preferably 5 to 7 μm can be used. In addition, when the carbon fiber has the form of a fabric, non-woven fabric or unidirectional material, a substance (fiber bundle) formed by bundling the carbon fiber in one direction can be used. In this case, as the fiber bundle, products formed by bundling 6000 (6K), 12000 (12K), 24000 (24K) or 60000 (60K) single fibers of carbon fiber supplied by a carbon fiber manufacturer can be directly used, or products formed by further bundling them can also be used.

[0200] The fiber bundle can be any of an untwisted yarn, a twisted yarn, and an untwisted yarn. The fiber bundle can be included in a state where the molded body has been opened, and sometimes it is included in the form of a fiber bundle without being opened.

[0201] When the carbon fiber has the form of a fabric, non-woven fabric or unidirectional material, a molded body can be obtained by impregnating the carbon fiber with a resin composition.

[0202] The carbon fiber can be a fiber with a sizing agent attached to its surface. When using carbon fiber with a sizing agent attached, the type of the sizing agent can be appropriately selected according to the types of the carbon fiber and the thermoplastic resin, and there is no particular limitation. The carbon fiber has been treated with an epoxy-based sizing agent, a urethane-based sizing agent, a polyamide-based sizing agent or contains no sizing agent, etc., and various products have been made. However, in the present invention, it can be used regardless of the type and presence or absence of the sizing agent.

[0203] The type of glass fiber is not particularly limited. For example, various glass fibers with different compositions such as E glass, low dielectric glass, and silica glass can be selected and used according to the purpose and application.

[0204] Single fibers of glass fiber with an average fiber diameter preferably of 5 - 20 μm, more preferably 7 - 17 μm can be used.

[0205] The glass fiber can be a fiber with a sizing agent attached to its surface. When using glass fiber with a sizing agent attached, the type of the sizing agent can be appropriately selected according to the type of glass fiber and is not particularly limited. The glass fiber has been processed with epoxy - based sizing agents, urethane - based sizing agents, vinyl acetate - based sizing agents or contains no sizing agent, etc., and has been made into various products. However, in the present invention, it can be used regardless of the type and presence or absence of the sizing agent. In addition, the above - mentioned sizing agents can be used in combination with silane coupling agents such as aminosilane, isocyanatosilane, and acrylic silane.

[0206] In one embodiment, the proportion of the resin composition (C) relative to the total amount of the fiber - reinforced resin composition (E) is 20 - 90% by mass, 30 - 80% by mass, or 40 - 75% by mass.

[0207] In one embodiment, the proportion of the reinforcing fiber (D) relative to the total amount of the fiber - reinforced resin composition (E) is 10 - 80% by mass, 20 - 70% by mass, or 25 - 60% by mass.

[0208] The fiber - reinforced resin composition (E) may or may not contain other components in addition to the resin composition (C) and the reinforcing fiber (D).

[0209] 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, 98% by mass or more, or substantially 100% by mass of the fiber - reinforced resin composition (E) is the resin composition (C) and the reinforcing fiber (D).

[0210] 3. Molded body

[0211] The molded body according to one embodiment of the present invention contains the resin composition (C) according to one embodiment of the present invention or the fiber - reinforced resin composition (E) according to one embodiment of the present invention.

[0212] According to the molded body of this embodiment, the resin composition (C) or the fiber - reinforced resin composition (E) has excellent moldability. Therefore, effects such as excellent productivity, processing accuracy, and mechanical properties can be obtained.

[0213] In the molded body, a part or all of the molded body is composed of the resin composition (C) or the fiber - reinforced resin composition (E).

[0214] In one embodiment, the molded body is an injection-molded body. In injection molding, a mold with a specified shape can be used for molding.

[0215] In one embodiment, the molded body is an extrusion-molded body. In extrusion molding, for example, a T-die can be used to mold the heat-melted resin composition (C) or the fiber-reinforced resin composition (E) into a film. Additionally, the obtained film can be softened by heating and molded into a specified shape.

[0216] In one embodiment, the molded body is a compression-molded body. In compression molding, for example, known methods such as cold compression molding and hot compression molding can be used.

[0217] Examples

[0218] Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples.

[0219] 1. Preparation of lignin component

[0220] (Production Example 1)

[0221] The lignin component (A-1) was produced by the following method.

[0222] (1) Extraction process

[0223] 100 parts by mass (68 parts by mass in terms of lignin) of the saccharification residue of herbaceous biomass (lignin content: 68% by mass), 68 parts by mass of phenol, 54 parts by mass of acetone, and 14 parts by mass of water were put into a pressure-resistant container capable of stirring, and heated and stirred at 3.0 MPa and 230 °C for 2 hours.

[0224] (2) Refining process

[0225] (2-1) Filtration

[0226] After dilution with acetone, the extract obtained through the above extraction process was put into a pressure filter equipped with No. 2 filter paper, and pressurized to 0.1 - 0.4 MPa with compressed air or nitrogen for filtration.

[0227] (2-2) Distillation

[0228] Using an evaporator, the filtrate obtained in the above (2-1) was heated (40 - 60 °C) under reduced pressure (5 - 10 kPa) for vacuum distillation to remove acetone. Additionally, using an evaporator, it was heated (100 - 140 °C) under reduced pressure for vacuum distillation to remove phenol.

[0229] (2-3) Vacuum drying

[0230] In order to remove the residual phenol in the above (2-2), heating is carried out under reduced pressure (1.0 to 5.0 kPa) (120 to 150 °C) for vacuum drying to remove phenol, and the lignin component (A-1) is obtained.

[0231] (Production Example 2)

[0232] 100 parts by mass (68 parts by mass in terms of lignin) of the saccharification residue of herbaceous biomass (lignin content: 68% by mass), 245 parts by mass of phenol, and 27 parts by mass of water are put into a pressure-resistant container capable of stirring, and heated and stirred at 1.7 MPa and 220 °C for 2 hours. Thereafter, through the same refining process as in Production Example 1, the lignin component (A-2) is obtained.

[0233] (Production Example 3)

[0234] 100 parts by mass (68 parts by mass in terms of lignin) of the saccharification residue of herbaceous biomass (lignin content: 68% by mass), 245 parts by mass of ethanol, and 27 parts by mass of water are put into a pressure-resistant container capable of stirring, and heated and stirred at 3.3 MPa and 200 °C for 2 hours. Thereafter, through the same refining process as in Production Example 1, the lignin component (A-3) is obtained.

[0235] (Production Example 4)

[0236] 100 parts by mass (42 parts by mass in terms of lignin) of the saccharification residue of woody biomass (lignin content: 42% by mass), 245 parts by mass of phenol, and 27 parts by mass of water are put into a pressure-resistant container capable of stirring, and heated and stirred at 1.8 MPa and 220 °C for 2 hours. Thereafter, through the same refining process as in Production Example 1, the lignin component (A-4) is obtained.

[0237] (Production Example 5)

[0238] 100 parts by mass (the parts by mass in terms of lignin) of the exploded oil palm empty fruit bunch (lignin content: 41% by mass), 245 parts by mass of phenol, and 27 parts by mass of water are put into a pressure-resistant container capable of stirring, and heated and stirred at 2.2 MPa and 240 °C for 2 hours. Thereafter, through the same refining process as in Production Example 1, the lignin component (A-5) is obtained.

[0239] In addition, as the lignin component (A), the following lignin components (A-6) and (A-7) are prepared.

[0240] Lignin component (A-6): Sulfate lignin (manufactured by SIGMA-ALDRICH Corporation, Lignin, alkali (product number 370959))

[0241] Lignin component (A-7): PEG-modified lignin

[0242] The following method is used to manufacture PEG-modified lignin (lignin modified with polyethylene glycol).

[0243] First, 100 parts by mass of polyethylene glycol with a number average molecular weight of 400 and 0.3 parts by mass of sulfuric acid as an acid catalyst are put into a reaction vessel and stirred. Next, 20 parts by mass of absolutely dry wood powder are put into the reaction vessel, and it is heated and stirred at 140°C for 90 minutes under normal pressure. Next, the reaction vessel is cooled, 120 parts by mass of sodium hydroxide (0.2 mol / L) are added, and it is stirred. Next, the obtained solid component is removed by filtration, and the solution component is recovered. Next, sulfuric acid is added to the obtained solution component to adjust the pH to 2.0. The obtained suspension is subjected to centrifugal separation to recover PEG-modified lignin, whereby PEG-modified lignin (lignin component (A-7)) is obtained.

[0244] [Evaluation method]

[0245] The following items are evaluated for lignin components (A-1) to (A-7).

[0246] (1) Phenol content

[0247] The phenol content is measured using high performance liquid chromatography (HPLC). Specifically, 50 mg of samples of lignin components (A-1) to (A-7) are each dissolved in 0.5 mL of tetrahydrofuran, 4.5 mL of a mixed solvent of water / acetonitrile at a volume ratio of 4 / 1 is added, stirred for 30 minutes, the supernatant is filtered, and a measurement sample is prepared. 1 μL of the measurement sample is injected into "ACQUITY UPLC H-CLASS" connected to a BEHC18 (1.7 μm × 2.1 mm × 50 mm) column. The column temperature is set to 40°C, the mobile phase uses a mixed solvent of 2 mM ammonium acetate aqueous solution (A) and acetonitrile (B), and a gradient method in which the flow rate ratio (A:B) is slowly changed from 80:20 to 10:90 is used, and measurement is performed at 280 nm using an ultraviolet-visible spectrophotometer (UV) detector in the detection section. The phenol content in the sample is calculated from the standard curve of a separately prepared standard phenol solution.

[0248] (2) Dimer components (compound shown in formula (1) and compound (2))

[0249] The content of the dimer components (phenol dimer and compound (2)) was determined by liquid chromatography-mass spectrometry (LC / MS). Specifically, 50 mg of the samples of the lignin components (A-1) to (A-7) were each dissolved in 0.5 mL of tetrahydrofuran, 4.5 mL of a mixed solvent of water / acetonitrile at 4 / 1 (volume ratio) was added, stirred for 30 minutes, and the supernatant was filtered to prepare the measurement sample. 1 μL of the measurement sample was injected into an LC-MS system of "ACQUITY UPLC H-CLASS" with a BEHC18 (1.7 μm × 2.1 mm × 50 mm) column connected to the separation section and "Xevo G2-XS QTof" mounted on the detection section. The column temperature was set at 40 °C, and the mobile phase used a mixed solvent of 2 mM ammonium acetate aqueous solution (A) and acetonitrile (B). A gradient method in which the flow rate ratio (A:B) was slowly changed from 80:20 to 10:90 was used to separate the dimer components.

[0250] After ionizing the obtained dimer components using an electrosprayer, the range of mass-to-charge ratio from 50 to 1000 was measured using a negative-mode quadrupole-time-of-flight mass spectrometer.

[0251] Assuming that all compounds were detected in the form of deprotonated species, based on the mass-to-charge ratio, the structures of the dimer components contained in the sample were determined as the following compounds (a) to (h) and compound (2). Chromatograms were extracted based on the mass-to-charge ratio corresponding to the structure of each compound, and the peak areas were calculated.

[0252] Based on the standard curve of a separately prepared standard 2,2'-dihydroxydiphenylmethane solution, the content of the phenol dimer component in the sample was calculated.

[0253] [Chemical formula 7]

[0254]

[0255] (3) GPC measurement of lignin components

[0256] Using gel permeation chromatography (GPC), the number-average molecular weight Mn, weight-average molecular weight Mw, Z-average molecular weight Mz, and molecular weight distribution (Mw / Mn) were measured. Specifically, samples of the lignin components (A-1) to (A-7) were each dissolved in tetrahydrofuran to prepare the measurement sample. 100 μL of the measurement sample was injected into a GPC system "HLC-8220GPC (manufactured by Tosoh Corporation)" or "HLC-8420GPC (manufactured by Tosoh Corporation)" in which two organic general columns "TSKgel GMHXL (manufactured by Tosoh Corporation)" filled with a styrene-based polymer and "G2000HXL (manufactured by Tosoh Corporation)" were connected in series. At 40 °C, the eluent tetrahydrofuran was developed at 1.0 mL / min, and the retention time was measured using differential refractive index (RI).

[0257] Calculate the average molecular weights of the samples according to the standard curve showing the relationship between the retention time and the molecular weight of the standard polystyrene prepared separately according to the indication.

[0258] It should be noted that a part of the sulfate lignin of the lignin component (A-6) and the PEG-modified lignin of the lignin component (A-7) are insoluble in tetrahydrofuran. Therefore, only the soluble components are taken as the analysis objects.

[0259] Calculate the following items (a) to (d) according to the molecular weight spectrum of the sample obtained by GPC.

[0260] (a) The molecular weight LogM at the peak maximum when the molecular weight LogM is 2.35 to 2.60

[0261] (The peak where the molecular weight LogM is 2.35 to 2.60)

[0262] Set the value of the molecular weight LogM at the peak maximum of the differential distribution value (dw / dLogM) when the molecular weight LogM of the molecular weight spectrum of the sample obtained by GPC (the spectrum plotted with the y-axis as dw / dLogM and the x-axis as LogM) is 2.35 to 2.60 as the "peak where the molecular weight LogM is 2.35 to 2.60".

[0263] (b) The maximum value of the differential distribution value (dw / dLogM)

[0264] In the molecular weight spectrum of the sample obtained by GPC (the spectrum plotted with the y-axis as dw / dLogM and the x-axis as LogM), set the maximum value of the differential distribution value (dw / dLogM) of the peak where the molecular weight LogM is between 2.35 and 2.60 as the "maximum value of the differential distribution value (dw / dLogM)".

[0265] (c) The integral distribution value (%) when the molecular weight LogM is 2.35, the integral distribution value (%) when the molecular weight LogM is 2.55

[0266] In the molecular weight spectrum of the sample obtained by GPC (the spectrum plotted with the y-axis as the integral distribution value (%) and the x-axis as LogM), set the integral distribution value (%) when the molecular weight LogM is 2.35 and the integral distribution value (%) when the molecular weight LogM is 2.55 as the "integral distribution value when the molecular weight LogM is 2.35" and the "integral distribution value when the molecular weight LogM is 2.55", respectively.

[0267] (d) The integral distribution value (%) from 2.55 to 2.35

[0268] The numerical value of the difference obtained by subtracting the integrated distribution value (%) with a molecular weight LogM of 2.35 from the integrated distribution value (%) with a molecular weight LogM of 2.55 is designated as "integrated distribution value (%) 2.55 - 2.35".

[0269] (4) Functional group content

[0270] A solvent mixture of deuterated chloroform, pyridine, and cyclohexanol (internal standard) is added to the lignin derivative or raw material (solid sample) obtained in each example. Further, 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane is added as a derivatization reagent, and the mixture is heated at 50 °C for 1 hour. Thereafter, the following measurement conditions are used for 31 P-NMR measurement.

[0271] It should be noted that both kraft lignin of the lignin component (A-6) and PEG-modified lignin of the lignin component (A-7) are insoluble in the solvent. Therefore, only the soluble components are measured.

[0272] < 31 P-NMR measurement>

[0273] The measuring apparatus and conditions are as follows.

[0274] · Pulse width: 30°

[0275] · Repetition time: 2 s

[0276] · Measurement range: -60 to 200 ppm

[0277] · Number of accumulations: 200 times

[0278] The signal from cyclohexanol as the internal standard is set at 145.2 ppm. Signals in the range of 150.0 - 145.5 ppm are identified as alcoholic hydroxyl groups, signals in the range of 144.7 - 136.6 ppm are identified as phenolic hydroxyl groups, and signals in the range of 136.6 - 133.6 ppm are identified as carboxyl groups. The amounts of alcoholic hydroxyl groups (mmol / g), phenolic hydroxyl groups (mmol / g), and carboxyl groups (mmol / g) are calculated based on the integral curve.

[0279] In addition, based on the above measurement results, the sum of the contents of alcoholic hydroxyl groups and carboxyl groups, and the ratio of the content of phenolic hydroxyl groups to the content of alcoholic hydroxyl groups (content of phenolic hydroxyl groups / content of alcoholic hydroxyl groups) are calculated.

[0280] (5) Physical properties (measurement of softening point)

[0281] Using a mortar, crush the sample (lignin component), and put 10 - 20 mg of the crushed sample into an aluminum cup (round, with an upper diameter of 60 mm, a lower diameter of 53 mm, and a depth of 15 mm). Place the aluminum cup containing the sample on a heating plate (IKAC - MAG HP7) and cover it with aluminum foil. After heating to 100 °C, increase the temperature in 10 °C increments and observe visually. By visual inspection, use the temperature at which dissolution occurs as the softening point, and thus determine the softening points (°C) of the lignin components (A - 1) to (A - 7).

[0282] The above results are shown in Table 1.

[0283] [Table 1]

[0284]

[0285] The content rate of "lignin" shown in Table 1 refers to the value calculated by regarding all components other than phenol dimers (compounds (a) - (h)), compound (2), and free phenol monomers among the components contained in the lignin component as "lignin" (the ratio of the content of "lignin" to the "total amount of lignin components"). In other words, the "total amount of lignin components" is the total amount of phenol dimers (compounds (a) - (h)), compound (2), free phenol monomers, and lignin.

[0286] In addition, the "total of compounds (a) - (h)" in Table 1 represents the proportion of the total amount of the compounds shown in formula (1) in the total amount of lignin components (the ratio of the total amount of the compounds shown in formula (1) to the "total amount of lignin components").

[0287] 2. Manufacture of resin composition

[0288] (Examples 1 - 11 and Comparative Examples 1 - 4)

[0289] According to the ratios (compositions) shown in Table 2, using a twin - screw kneader with a barrel diameter of 11 mm (manufactured by ThermoFisher Scientific, Process11), melt - knead the lignin component (A) and the thermoplastic resin (B) at 250 °C to obtain resin compositions (C - 1) to (C - 15).

[0290] Here, as the lignin component (A), use the above - mentioned lignin components (A - 1) to (A - 7). In addition, as the thermoplastic resin (B), use the following thermoplastic resins (B - 1), (B - 2).

[0291] Thermoplastic resin (B - 1): PA6 (manufactured by UBE Corporation, UBE Nylon 1022B)

[0292] Thermoplastic resin (B-2): PA610 (manufactured by EVONIK, VESTAMID Terra HS16)

[0293] [Evaluation method]

[0294] For the resin compositions (C-1) to (C-15), the following matters were evaluated.

[0295] (1) Molding processability (melt compounding property)

[0296] When the strands extruded from the twin-screw mixer could be stably maintained for 10 minutes and the pressure of the resin composition fell within ±50% before and after the start of melt compounding, it was evaluated as "〇". Cases that did not meet these conditions or cases where the melt compounded material was gelled were evaluated as "×".

[0297] (2) Mechanical properties

[0298] (2-1) Tensile strength and elongation at break

[0299] For the granular resin composition, using an injection molding machine (manufactured by Thermo Fisher Scientific, MiniJetPro), injection molding was carried out under the conditions of a barrel temperature of 250°C and a mold temperature of 90°C to obtain a tensile test piece (2 mm thick). The mold used was ISO527-2-5A manufactured by Thermo Fisher Scientific. For the above-obtained tensile test piece, the tensile properties were measured in accordance with ISO 527. Specifically, the tensile strength (MPa) and elongation at break (%) were measured under the conditions of a chuck distance of 5 cm, a temperature of 23°C, and a tensile speed of 20 mm / min. The larger the value, the better the tensile properties.

[0300] (2-2) Flexural modulus and flexural strength

[0301] For the granular resin composition, using an injection molding machine (manufactured by Thermo Fisher Scientific, MiniJetPro), injection molding was carried out under the conditions of a barrel temperature of 250°C and a mold temperature of 90°C to obtain a flexural test piece (2 mm thick). The mold used was ISO527-2-5A manufactured by Thermo Fisher Scientific. For the above-obtained flexural test piece, the flexural properties were measured in accordance with ISO 178:2010. Specifically, the flexural strength (MPa) and flexural modulus (GPa) were measured under the conditions of a span of 5 cm, a temperature of 23°C, and a flexural speed of 3 mm / min. The larger the value, the better the flexural properties.

[0302] The above results are shown in Table 2.

[0303] [Table 2]

[0304]

[0305] [Evaluation]

[0306] As can be seen from Table 2, the resin compositions (C-1) to (C-11) of Examples 1 to 11 have excellent moldability and mechanical properties.

[0307] 3. Manufacture of Fiber Reinforced Resin Composition

[0308] (Examples 12 to 19 and Comparative Examples 5 to 8)

[0309] According to the formulation (composition) shown in Table 3, using a twin-screw kneader (manufactured by ThermoFisher Scientific, Process11) with a barrel diameter of 11 mm, the resin composition (C) and the reinforcing fiber (D) were melt-kneaded at 250 °C to obtain fiber reinforced resin compositions (E-1) to (E-12).

[0310] Here, as the resin composition (C), the above-mentioned lignin components (C-1) to (C-6), (C-12) and (C-13) were used. In addition, as the reinforcing fiber (D), the following reinforcing fibers (D-1) and (D-2) were used.

[0311] Reinforcing fiber (D-1): Carbon fiber (manufactured by Mitsubishi Chemical Corporation, Pyrofil TR066A)

[0312] Reinforcing fiber (D-2): Glass fiber (manufactured by Nippon Electric Glass Co., Ltd., E glass fiber chopped strand T-249H)

[0313] [Evaluation Method]

[0314] For the fiber reinforced resin compositions (E-1) to (E-12), the same evaluation was carried out as for the resin compositions (C-1) to (C-15). Among them, the measurement of the elongation at break in tension was omitted.

[0315] The results are shown in Table 3.

[0316] [Table 3]

[0317]

[0318] [Evaluation]

[0319] As can be seen from Table 3, the fiber-reinforced resin compositions (E-1) to (E-8) of Examples 12 to 19 have excellent moldability and mechanical properties. It can also be seen that the fiber-reinforced resin compositions (E-1) to (E-8) of Examples 12 to 19 can reduce the amount of resin used because they contain a lignin composition, and, compared with the fiber-reinforced resin compositions (E-9) to (E-12) of Comparative Examples 5 to 8 that do not contain a lignin composition, exhibit equivalent or not significantly inferior properties.

[0320] As described above, several embodiments and / or examples of the present invention have been described in detail. However, those skilled in the art can easily make various changes to the embodiments and / or examples exemplified thereby without substantially departing from the new teachings and effects of the present invention. Therefore, these various changes are included within the scope of the present invention.

[0321] The entire contents of the documents described in this specification and the applications that form the basis of the priority of this application based on the Paris Convention are incorporated herein by reference.

Claims

1. A resin composition comprising a lignin component (A) and a thermoplastic resin (B), wherein the content of alcoholic hydroxyl groups in the lignin component (A) is 1.5 mmol / g or less, the content of the lignin component (A) is 1 to 60% by mass, the content of the thermoplastic resin (B) is 40 to 99% by mass.

2. The resin composition according to claim 1, wherein, The total content of alcoholic hydroxyl groups and carboxyl groups in the lignin component (A) is 1.6 mmol / g or less.

3. The resin composition according to claim 1 or 2, wherein, The content of phenolic hydroxyl groups in the lignin component (A) is 2.5 mmol / g or more, and the ratio of the content of phenolic hydroxyl groups to the content of alcoholic hydroxyl groups (content of phenolic hydroxyl groups / content of alcoholic hydroxyl groups) is 2.5 or more.

4. The resin composition according to any one of claims 1 to 3, wherein, The weight average molecular weight (Mw) of the lignin component (A) is 1000 to 3500.

5. The resin composition according to any one of claims 1 to 4, wherein, The softening point of the lignin component (A) is 100°C or higher and lower than 250°C.

6. The resin composition according to any one of claims 1 to 5, wherein, The lignin component (A) contains two or more compounds represented by the following formula (1), and the proportion of the total amount of the compounds represented by the formula (1) relative to the total amount of the lignin component (A) is 0.06% by mass or more, [Chemical formula 8] In formula (1), * is bonded to a carbon atom on the ring substituted with any one of R 11 ~R 15 ; ** is bonded to a carbon atom on the ring substituted with any one of R 16 ~R 20 ; R a is a hydrogen atom, a methyl group, an ethyl group, a furyl group, a hydroxymethylfuryl group, a hydroxyphenyl group, a hydroxymethoxyphenyl group or a hydroxydimethoxyphenyl group; R c1 , R c2 each independently represents a hydroxyl group, an alkoxy group, an amino group or a mercapto group; R 11 ~R 20 each independently represents a hydrogen atom, a hydroxyl group, a hydrocarbon group having 1 to 15 carbon atoms, a hydrocarbon ether group having 1 to 15 carbon atoms, or a group containing a carbonyl group; R 11 ~R 20 are optionally the same as or different from each other, wherein at least one of R 11 ~R 15 is a hydrogen atom, and at least one of R 16 ~R 20 is a hydrogen atom.

7. The resin composition according to any one of claims 1 to 6, wherein, The maximum value of the differential distribution value (dw / dLogM) of the peak existing at a molecular weight LogM of 2.35 to 2.60 measured by gel permeation chromatography (GPC) is 50 or more and 150 or less, or the difference in the integral distribution value (%) at a molecular weight LogM of 2.35 to 2.55 is 5 or more and 15 or less.

8. The resin composition according to any one of claims 1 to 7, wherein, The thermoplastic resin (B) comprises a polycondensation polymer.

9. The resin composition according to any one of claims 1 to 8, wherein, The thermoplastic resin (B) comprises one or more selected from polyamide resins, polyester resins, and polycarbonate resins.

10. A fiber-reinforced resin composition comprising the resin composition according to any one of claims 1 to 9 and a reinforcing fiber (D).

11. The fiber-reinforced resin composition according to claim 10, wherein, The reinforcing fiber (D) comprises one or more selected from carbon fibers, glass fibers, aramid fibers, and cellulose fibers.

12. A molded article comprising the resin composition according to any one of claims 1 to 9, or the fiber-reinforced resin composition according to claim 10 or 11.

13. The molded article according to claim 12, which is an injection molded article.

14. The molded article according to claim 12, which is an extrusion molded article.

15. The molded article according to claim 12, which is a compression molded article.

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