Thermoplastic resin sorting method and recycled resin producing method

Abstract

It cannot be said that it has hitherto been possible, with a simple method, to separate a desired thermoplastic resin from a mixture containing various kinds of thermoplastic resins. Further, the difficulty in the separation has caused trouble in recycling thermoplastic resins being waste materials, scrap materials, and the like.　The abovementioned problem is solved by a thermoplastic resin sorting method characterized by having: a detection step of irradiating a plurality of types of thermoplastic resins with UV light and detecting a fluorescence spectrum emitted from the thermoplastic resins; and a sorting step of sorting out one of the plurality of thermoplastic resins on the basis of the fluorescence spectrum.

Description

Method for sorting thermoplastic resins and method for producing recycled resins

[0001] The present invention relates to a method for sorting thermoplastic resins, a method for producing recycled resins, and more particularly to a method for sorting a predetermined thermoplastic resin from a mixture containing multiple types of thermoplastic resins.

[0002] Thermoplastic resins are extremely useful resins used in a wide variety of fields in daily life. For this reason, many types of thermoplastic resins have been developed and are used for various applications. Furthermore, the manufacturing process using thermoplastic resins typically generates excess scraps, such as spools and runners discarded after molding. Therefore, the recycling of waste and scraps from thermoplastic resins is attracting considerable attention.

[0003] Furthermore, monitoring methods for understanding the state of thermoplastic resins and other materials, and methods for authenticating and identifying resin compositions for film manufacturing are known (for example, Patent Documents 1 to 3).

[0004] Japanese Patent Publication No. 2013-137199, Japanese Patent Publication No. 2023-041655, Japanese Patent Publication No. 2024-125908

[0005] As mentioned above, thermoplastic resins are used in a wide range of fields, and there are many different types. Even using conventional methods to understand and identify the state of these numerous types of thermoplastic resins, it has not always been easy to identify, select, and sort multiple types of thermoplastic resins. Therefore, conventional methods have not allowed for the simple separation of desired materials from mixtures containing various types of thermoplastic resins, and this difficulty in separation has been one of the causes of problems in the recycling of thermoplastic resins as waste materials and scraps.

[0006] According to the present invention, it is possible to easily and reliably select a predetermined thermoplastic resin from a mixture containing multiple types of thermoplastic resins. Furthermore, according to the present invention, thermoplastic resins contained in waste resin materials can be effectively reused. The present invention includes at least the following: [1] A method for selecting thermoplastic resins, comprising: a detection step of irradiating multiple types of thermoplastic resins with UV light and detecting the fluorescence spectrum emitted from the thermoplastic resins; and a selection step of selecting one of the multiple thermoplastic resins based on the fluorescence spectrum. [2] The selection method according to [1], further comprising a comparison step of comparing the detected fluorescence spectrum with the fluorescence spectrum of a sample measured in advance. [3] The selection method according to [1] or [2], for example, the method according to [1], wherein the wavelength of the UV light is 300 to 400 nm. [4] The selection method according to any of [1] to [3], for example, the method according to [1], wherein in the detection step, the fluorescence spectrum is detected by a hyperspectral camera. [5] The sorting method according to any of [1] to [4] above, for example, the method according to [1] above, wherein in the detection step, the sample of the thermoplastic resin is placed on a black base and the UV light is directly irradiated onto the sample. [6] The sorting method according to any of [1] to [5] above, for example, the method according to [1] above, wherein the wavelength range of the fluorescence spectrum is 380 to 1000 nm. [7] The sorting method according to any of [2] to [6] above, for example, the method according to [2] above, wherein in the comparison step, the wavelength values ​​of the peak tops in a plurality of fluorescence spectra are compared. [8] The sorting method according to any of [2] to [7] above, for example, the method according to [2] above, wherein in the comparison step, a plurality of waveforms showing the intensity and wavelength of the fluorescence spectrum are compared with each other.

[0007] [9] A sorting method according to any of [1] to [8] above, for example, the method described in [1] above, wherein the thermoplastic resin that is the target of the detection step includes at least one of the constituent units b to d represented by the following formulas, wherein the constituent unit b is selected from the group consisting of a monomer-derived constituent unit (b-1) represented by the following general formula (1-1), a monomer-derived constituent unit (b-2) represented by the following general formula (1-2), and a monomer-derived constituent unit (b-3) represented by the following general formula (1-3), the constituent unit c includes a monomer-derived constituent unit (c) represented by the following general formula (2), and the constituent unit d is selected from the group consisting of the following general formulas (7) to (10). [In general formula (1-1), R ａ and R ｂ Each of these independently comprises a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group comprising one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S; m and n each independently represent an integer from 0 to 5; and X represents a single bond, -O-, -S-, -SO-, -SO ２ A divalent group represented by -, -CO-, or any of the following general formulas (3) to (6), (In general formulas (3) to (6), R ９ and R １０Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; R １３ to R １６ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; R １７ to R ２６ Each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms, and at least one of R １７ to R ２６ is an alkyl group having 1 to 3 carbon atoms.) A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. ]

[0008] [In general formula (1-2), R ａ and R ｂ Each of these independently comprises a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, an optionally substituted C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from O, N, and S, an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from the group consisting of R ｈ is an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 3 to 20 carbon atoms that may have substituents and contains one or more heterocyclic atoms selected from O, N, and S; X is a single bond or an optionally substituted fluorene group; A and B are each independently an optionally substituted alkylene group having 1 to 5 carbon atoms; m and n are each independently an integer from 0 to 6, preferably an integer from 0 to 3; a and b are each independently an integer from 0 to 10, preferably an integer from 1 to 3; R' and R'' are each independently selected from the group consisting of a hydroxyl group, a halogen atom, an optionally substituted alkoxy group having 1 to 20 carbon atoms, and an optionally substituted aryloxy group having 6 to 20 carbon atoms.

[0009] [In general formula (1-3a), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, and an optionally substituted C6-C20 aryl group; R''' is a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ [wherein is a C6-C20 aryl group which may have substituents, or a C3-C20 heteroaryl group which contains one or more heterocyclic atoms selected from O, N, and S and may have substituents, and n is an integer from 0 to 6.] [In general formula (2), R ｃ and R ｄ Each of these independently comprises a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group comprising one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S, and p and q each independently represent an integer from 0 to 5, Y １ These are single bonds, -O-, -S-, -SO-, -SO ２A divalent group represented by -, -CO-, or any of the following general formulas (3) to (6), (In general formulas (3) to (6), R ９ and R １０ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R ９ and R １０ These elements bond to each other to form a carbon ring or heterocycle with 3 to 20 carbon atoms; c represents an integer from 0 to 20; R １１ and R １２ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R １１ and R １２ They bond to each other to form a carbon ring or heterocycle with 3 to 20 carbon atoms; R １３ ~R １６ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R １３ and R １４ and R １５ and R １６ Each of these atoms bonds with the others to form a carbon ring or heterocycle with 3 to 20 carbon atoms; R １７ ~R ２６ Each of these independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms, R １７ ~R ２６At least one of them is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer from 0 to 10.

[0010] [In general formulas (7) to (10), X ｇ Each of these independently represents an alkylene group having 1 to 10 carbon atoms, and R ｊ , R ｋ , and R ｌ Each of these independently comprises a halogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C20 cycloalkoxy group, a substituted or unsubstituted C6-C20 aryl group, a C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from substituted or unsubstituted O, N, and S, a substituted or unsubstituted C6-C20 aryloxy group, and -C≡C-R ｉ Selected from, R ｉ represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms containing one or more heterocyclic atoms selected from O, N, and S, p independently represents an integer of 0 or 1, q, r, and s independently represent an integer of 0 to 10, t represents an integer of 1 to 3, where q is 2 or greater and there are two R ｊ If present on an adjacent carbon atom, two R ｊ They may come together to form a ring structure, and r is 2 or more, and two R ｋ If present on an adjacent carbon atom, two R ｋ They may come together to form a ring structure, and s is 2 or more, and two R ｌ If present on an adjacent carbon atom, two R ｌ They may come together to form a ring structure, R ｍ R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ｇ [This represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.]

[0011]

[10] The thermoplastic resin comprises at least one of thermoplastic resins B to D, wherein the thermoplastic resin B comprises one or more selected from the group consisting of thermoplastic resin B1 comprising a monomer-derived constituent unit (b-1) represented by the general formula (1-1), thermoplastic resin B2 comprising a monomer-derived constituent unit (b-2) represented by the general formula (1-2), and thermoplastic resin B3 comprising a monomer-derived constituent unit (b-3) represented by the general formula (1-3a), the thermoplastic resin C comprises a monomer-derived constituent unit (c) represented by the general formula (2), and the thermoplastic resin D comprises at least one constituent unit selected from the group consisting of the general formulas (7) to (10), the sorting method according to any of [1] to [9] above, for example, the sorting method according to [9] above.

[11] The constituent unit (b-3) is derived from a monomer represented by the following general formula (1-3), In general formula (1-3), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have substituents, and an aryl group having 6 to 20 carbon atoms which may have substituents, any of the above [1] to [9], for example, the selection method described in [9].

[0012]

[12] A sorting method according to any of [1] to

[11] above, for example, the sorting method according to [1] above, wherein the sorting step sorts the thermoplastic resin contained in the waste resin material.

[13] A method for producing recycled resin, wherein the sorting method according to

[12] above produces the thermoplastic resin as recycled resin from the waste resin material.

[0013] According to the present invention, a thermoplastic resin can be easily and reliably selected from among several thermoplastic resins based on the fluorescence spectrum emitted when the thermoplastic resin is irradiated with UV light. This method of identifying a desired thermoplastic resin from among several thermoplastic resins using a simple method facilitates the reuse of thermoplastic resins, thereby expanding recycling and reducing environmental impact.

[0014] The present invention will now be described in detail. The thermoplastic resin sorting method of the present invention comprises at least a detection step of detecting the fluorescence spectrum of a thermoplastic resin and a sorting step of sorting one of a plurality of thermoplastic resins based on the fluorescence spectrum. Thus, the object to be sorted in the sorting step is a thermoplastic resin composition which is a mixture having at least a plurality of thermoplastic resins. However, the object to be sorted may be a thermoplastic resin composition which includes components other than thermoplastic resins, such as additives.

[0015] 1. Detection Process In the detection process, the fluorescence spectrum from the thermoplastic resin irradiated with UV light is detected. There are no particular limitations on the type of thermoplastic resin that is selected as a specific type based on the detection of its fluorescence spectrum. However, examples of thermoplastic resins to be detected and selected include those having the following constituent units.

[0016] 1-1. Thermoplastic resins to be detected and sorted include, for example, any of the following constituent units. That is, thermoplastic resins include, for example, a monomer-derived constituent unit (b-1) represented by the following general formula (1-1), a monomer-derived constituent unit (b-2) represented by the general formula (1-2), a monomer-derived constituent unit (b-3) represented by the following general formula (1-3a), a monomer-derived constituent unit (c) represented by the following general formula (2), and at least one constituent unit (d) selected from the group consisting of the following general formulas (7) to (10). Hereinafter, the monomer-derived constituent units (b-1) to (b-3) represented by formulas (1-1) to (1-3a), respectively, will be collectively referred to as constituent unit b. Also, the monomer-derived constituent unit (c) represented by formula (2) will be simply referred to as constituent unit c, and the monomer-derived constituent unit (d) represented by formula (3) will be simply referred to as constituent unit d.

[0017] (i) The thermoplastic resin constituent unit b, which includes constituent unit b, for example, a monomer-derived constituent unit (b-1) represented by the following formula (1-1). In general formula (1-1), R ａ and R ｂEach of these independently comprises a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group comprising one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ R represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S. ａ and R ｂ Preferably, m and n are independently selected from optionally substituted C1-C10 alkyl groups and optionally substituted C6-C12 aryl groups, and more preferably, independently selected from optionally substituted C1-C6 alkyl groups and optionally substituted C6-C10 aryl groups. In general formula (1-1), m and n each independently represent an integer from 0 to 5, preferably an integer from 0 to 3, more preferably an integer of 0 or 1, and particularly preferably 0. In general formula (1-1), X is a single bond, -O-, -S-, -SO-, -SO ２ It is a divalent group represented by -, -CO-, or one of the following general formulas (3) to (6).

[0018] In general formulas (3) to (6), R ９ and R １０ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R ９ and R １０are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms, preferably a carbocyclic ring having 6 to 12 carbon atoms or a heterocyclic ring having 6 to 12 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms, preferably a carbocyclic ring having 6 to 12 carbon atoms or a heterocyclic ring having 6 to 12 carbon atoms; R １３ to R １６ each independently represents hydrogen, halogen, an alkyl group having 3 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms, preferably a carbocyclic ring having 6 to 12 carbon atoms or a heterocyclic ring having 6 to 12 carbon atoms; R １７ to R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms, and at least one of R １７ to R ２６ is an alkyl group having 1 to 3 carbon atoms.) A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of from 0 to 10.

[0019] Specific examples of monomer-derived constituent units (b-1) represented by formula (1-1) include constituent units derived from 2,2'-bis(1-hydroxymethoxy)-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (also referred to as "BHEBN"), 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene, and the like. In one embodiment, the constituent unit represented by formula (1-1) is a constituent unit derived from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BHEBN).

[0020] The constituent unit b includes, for example, a monomer-derived constituent unit (b-2) represented by the following formula (1-2). In general formula (1-2), R ａ and R ｂ Each of these independently comprises a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, an optionally substituted C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from O, N, and S, an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from the group consisting of, preferably a heteroaryl group having 3 to 20 carbon atoms that may have substituents, comprising a hydrogen atom, an aryl group having 6 to 20 carbon atoms that may have substituents, and one or more heterocyclic atoms selected from O, N, and S, more preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms that may have substituents, and even more preferably a hydrogen atom, an aryl group having 6 to 12 carbon atoms that may have substituents, R ｈ R represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents, for example, a heteroaryl group having 6 to 12 carbon atoms which contains one or more heterocyclic atoms selected from O, N, and S.ａ and R ｂ is preferably independently selected from an alkyl group having 1 to 10 carbon atoms which may have a substituent, and an aryl group having 6 to 12 carbon atoms which may have a substituent, more preferably independently selected from an alkyl group having 1 to 6 carbon atoms which may have a substituent, and an aryl group having 6 to 10 carbon atoms which may have a substituent.

[0021] Further, in General Formula (1-2), X represents a single bond or a fluorene group which may have a substituent, preferably a single bond or a fluorene group which may have a substituent having a total carbon number of 12 to 20, A and B are each independently an alkylene group having 1 to 5 carbon atoms which may have a substituent, preferably an alkylene group having 2 or 3 carbon atoms, m and n are each independently an integer of 0 to 6, preferably an integer of 0 to 3, more preferably 0 or 1, a and b are each independently an integer of 0 to 10, preferably an integer of 1 to 3, more preferably 1 or 2, R' and R'' are each independently selected from the group consisting of a hydroxy group, a halogen atom, an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and an aryloxy group having 6 to 20 carbon atoms which may have a substituent, preferably a hydroxy group, a linear alkoxy group having 1 to 5 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, and more preferably a hydroxy group, a methoxy group, an ethoxy group, a phenyloxy group (phenoxy group).

[0022] Specific examples of the structural unit (b-2) derived from the monomer represented by Formula (1-2) include structural units derived from 2,2'-([1,1'-binaphthalene]-2,2'-diylbis(oxy))acetoacetic acid (BINOL-DC) and its methyl ester, ethyl ester, phenyl ester, etc.

[0023] Further, the structural unit b includes, for example, a structural unit (b-3) derived from a monomer represented by the following formula (1-3a). In general formula (1-3a), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, and an optionally substituted C6-C20 aryl group. Preferably, R' and R'' are each independently selected from a hydrogen atom, an optionally substituted C1-C10 alkyl group, and an optionally substituted C6-C12 aryl group, and more preferably, each is independently selected from a hydrogen atom, an optionally substituted C1-C6 alkyl group, and an optionally substituted C6-C10 aryl group. Furthermore, in general formula (1-3a), R''' is a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from the above. In general formula (1-3a), R''' is preferably an alkyl group having 1 to 20 carbon atoms which may be substituted, an aryl group having 6 to 20 carbon atoms which may be substituted, or an aryl group having 3 to 20 carbon atoms which may be substituted, more preferably an alkyl group having 1 to 10 carbon atoms which may be substituted, or an aryl group having 6 to 12 carbon atoms which may be substituted, and even more preferably an alkyl group having 1 to 6 carbon atoms which may be substituted, or an aryl group having 6 to 10 carbon atoms which may be substituted. ｈ represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S. In general formula (1-3a), n represents an integer from 0 to 6, preferably an integer from 0 to 3, more preferably 0 or 1, and particularly preferably 0.

[0024] The constituent unit (b-3) is preferably derived from a monomer represented by the following formula (1-3). That is, the monomer of general formula (1-3a) is preferably represented by the following formula (1-3). In general formula (1-3), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, and an optionally substituted C6-C20 aryl group. Preferably, R' and R'' are each independently selected from a hydrogen atom, an optionally substituted C1-C10 alkyl group, and an optionally substituted C6-C12 aryl group, and more preferably, each is independently selected from a hydrogen atom, an optionally substituted C1-C6 alkyl group, and an optionally substituted C6-C10 aryl group.

[0025] Specific examples of monomer-derived constituent units (b-3) represented by formula (1-3) include constituent units derived from naphthalene-2,6-dicarboxylic acid and its methyl ester, ethyl ester, phenyl ester, etc.

[0026] (ii) The thermoplastic resin constituent unit c containing the constituent unit c includes, for example, a monomer-derived constituent unit (c) represented by the following formula (2). In general formula (2), R ｃ and R ｄ Each of these independently comprises a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group comprising one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈR represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S. C and R ｄ Preferably, each is independently selected from an alkyl group having 1 to 10 carbon atoms which may have substituents, and an aryl group having 6 to 12 carbon atoms which may have substituents, and more preferably, each is independently selected from an alkyl group having 1 to 6 carbon atoms which may have substituents, and an aryl group having 6 to 10 carbon atoms which may have substituents. In general formula (2), p and q each independently represent an integer from 0 to 5, preferably an integer from 0 to 3, more preferably an integer of 0 or 1, and particularly preferably 0. Also, Y in general formula (2) １ These are single bonds, -O-, -S-, -SO-, -SO ２ It is a divalent group represented by -, -CO-, or one of the following general formulas (3) to (6).

[0027] In general formula (3), R ９ and R １０ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R ９ and R １０ These elements bond to each other to form a carbon ring or heterocycle having 3 to 20 carbon atoms, preferably a carbon ring or heterocycle having 6 to 12 carbon atoms; c represents an integer from 0 to 20.

[0028] In general formula (4), R １１ and R １２Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R １１ and R １２ These atoms bond to each other to form a carbon ring or heterocycle having 3 to 20 carbon atoms, preferably a carbon ring or heterocycle having 6 to 12 carbon atoms.

[0029] In general formula (5), R １３ ~R １６ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R １３ and R １４ and R １５ and R １６ These atoms bond to each other to form a carbon ring or heterocycle having 3 to 20 carbon atoms, preferably a carbon ring or heterocycle having 6 to 12 carbon atoms.

[0030] (iii) The thermoplastic resin constituent unit d containing constituent unit d includes, for example, a monomer-derived constituent unit (d) represented by any of the following formulas (7) to (10). In general formulas (7) to (10), X ｇ Each of these independently represents an alkylene group having 1 to 10 carbon atoms, and R ｊ , R ｋ , and R ｌEach of these independently comprises a halogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C20 cycloalkoxy group, a substituted or unsubstituted C6-C20 aryl group, a C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from substituted or unsubstituted O, N, and S, a substituted or unsubstituted C6-C20 aryloxy group, and -C≡C-R ｉ Selected from, R ｉ This represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms containing one or more heterocyclic atoms selected from O, N, and S.

[0031] In general formulas (7) to (9), p independently represents an integer of 0 or 1, q, r, and s independently represent an integer from 0 to 10, t represents an integer from 1 to 3, where q is 2 or greater and there are two R ｊ If present on an adjacent carbon atom, two R ｊ They may come together to form a ring structure, and r is 2 or more, and two R ｋ If present on an adjacent carbon atom, two R ｋ They may come together to form a ring structure, and s is 2 or more, and two R ｌ If present on an adjacent carbon atom, two R ｌ They may come together to form a ring structure, R ｍ This represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0032] In general formula (10), R ｇ This represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0033] Examples of halogen atoms mentioned above include fluorine, chlorine, bromine, and iodine atoms.

[0034] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and eicosyl groups. Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and pentyl groups.

[0035] Examples of the above-mentioned alkoxy groups having 1 to 20 carbon atoms include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, and eicosyloxy groups. Examples of alkoxy groups having 1 to 10 carbon atoms include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, and decyloxy groups. Examples of alkoxy groups having 1 to 6 carbon atoms include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, and hexyloxy groups.

[0036] Examples of the above-mentioned cycloalkyl groups having 5 to 20 carbon atoms include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentadecyl, cyclooctadecyl, bicyclo[2.2.1]heptyl, and bicyclo[2.2.2]octyl groups. Examples of cycloalkyl groups having 5 to 10 carbon atoms include cyclopentyl, cyclohexyl, cycloheptyl, bicyclo[2.2.1]heptyl, and bicyclo[2.2.2]octyl groups.

[0037] Examples of the above-mentioned cycloalkoxy groups having 5 to 20 carbon atoms include cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclododecyloxy, cyclotridecyloxy, cyclotetradecyloxy, cyclopentadecyloxy, cyclooctadecyloxy, bicyclo[2.2.1]heptyloxy, and bicyclo[2.2.2]octyloxy.

[0038] Examples of the above-mentioned aryl groups having 6 to 20 carbon atoms include phenyl group, tolyl group, xylyl group, trimethylphenyl group, tetramethylphenyl group, ethylphenyl group, ethylmethylphenyl group, diethylphenyl group, propylphenyl group, isopropylphenyl group, isopropylmethylphenyl group, benzyl group, phenethyl group, phenylpropyl group, naphthyl group, anthracenyl group, phenantrenyl group, naphthacenyl group, chrycerinyl group, pyrenyl group, biphenyl group, terphenyl group, quaterphenyl group, and the like.

[0039] As heteroaryl groups having 3 to 20 carbon atoms and containing one or more heterocyclic atoms selected from the above O, N, and S, the following are included: furanyl group, benzofuranyl group, isobenzofuranyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, pyridyl group, pyridyl group, pyrimidyl group, pyridazyl group, pyrrolidyl group, indolyl group, isoindolyl group, indazolyl group, quinolyl group, isoquinolyl group, naphthylyl group, quinoxalyl group, quinazolyl group, Examples include pteridyl group, phenanthridyl group, acridinyl group, pyrimidinyl group, phenanthrolinyl group, phenazinyl group, thiophenyl group, thiopyranyl group, benzothiophenyl group, benzothiopyranyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, flazanyl group, oxadiazolyl group, dithiazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, and benzoisothiazolyl group.

[0040] Examples of the above-mentioned aryloxy groups having 6 to 20 carbon atoms include phenyloxy group, tolyloxy group, xyloxy group, trimethylphenyloxy group, tetramethylphenyloxy group, ethylphenyloxy group, ethylmethylphenyloxy group, diethylphenyloxy group, propylphenyloxy group, isopropylphenyloxy group, isopropylmethylphenyloxy group, naphthyloxy group, anthracenyloxy group, phenantrenyloxy group, naphthacenyloxy group, chrycerinyloxy group, pyrenyloxy group, biphenyloxy group, terphenyloxy group, quaterphenyloxy group, etc. Examples of the above-mentioned aryloxy groups having 6 to 10 carbon atoms include phenyloxy group, tolyloxy group, xylyloxy group, trimethylphenyloxy group, tetramethylphenyloxy group, ethylphenyloxy group, ethylmethylphenyloxy group, diethylphenyloxy group, propylphenyloxy group, isopropylphenyloxy group, isopropylmethylphenyloxy group, naphthyloxy group, etc.

[0041] As mentioned above, R ｉ R represents a heteroaryl group having 3 to 20 carbon atoms that contains an aryl group having 6 to 20 carbon atoms or one or more heterocyclic atoms selected from O, N, and S. Examples of heteroaryl groups having 3 to 20 carbon atoms that contain an aryl group having 6 to 20 carbon atoms or one or more heterocyclic atoms selected from O, N, and S include those mentioned above. Among these, R ｉ The group is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group.

[0042] Examples of alkylene groups having 1 to 10 carbon atoms include methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, and pentylene. Of these, methylene, ethylene, propylene, butylene, isobutylene, and sec-butylene are preferred, and methylene, ethylene, and propylene are more preferred.

[0043] In the above formula, the types of substituents that "may have substituents" are not particularly limited, but include halogen atoms, C1-C10 alkyl groups, C5-C10 cycloalkyl groups, C1-C10 alkoxy groups, C5-C10 cycloalkoxy groups, C2-C10 alkyloxycarbonyl groups, C5-C10 cycloalkyloxycarbonyl groups, C7-C15 aryloxycarbonyl groups, C2-C10 alkylcarbonyloxy groups, C5-C10 cycloalkylcarbonyloxy groups, C7-C15 arylcarbonyloxy groups, C2-C10 hydroxyalkylcarbonyl groups, glycidyloxycarbonyl groups, hydroxyl groups, carboxyl groups, cyano groups, C1-C10 amide groups, etc. The range of carbon atoms specified for the monomer compound in the above formula includes the number of carbon atoms in the substituents.

[0044] The thermoplastic resin to be identified in the method for identifying thermoplastic resins preferably contains any of the above-described constituent units b to d, but may also be, for example, the following. That is, the thermoplastic resin is, for example, a thermoplastic resin B that contains one or more selected from the group consisting of thermoplastic resin B1 containing a monomer-derived constituent unit (b-1) represented by the above general formula (1-1), thermoplastic resin B2 containing a monomer-derived constituent unit (b-2) represented by the above general formula (1-2), and thermoplastic resin B3 containing a monomer-derived constituent unit (b-3) represented by the above general formula (1-3a). Furthermore, thermoplastic resin B may consist of only one type of constituent unit (b-1) to (b-3), may have two or three types, may consist of only two types of constituent units (b-1) to (b-3), or may consist of (b-1) to (b-3). The thermoplastic resin is, for example, a thermoplastic resin C that contains a monomer-derived constituent unit (c) represented by the above general formula (2), or consists only of constituent units (c) derived from (c). Furthermore, the thermoplastic resin D is, for example, a thermoplastic resin D that includes at least one constituent unit (d) derived from a monomer selected from the group consisting of the general formulas (7) to (10) above, or consists only of constituent unit (c).

[0045] Examples of the thermoplastic resin B1 include, but are not limited to, the following: PC-1, PC-2, PC-4, PC-7, etc. In these formulas, l, m, and n are each independently integers of 1 or more, for example, 1 to 5.

[0046] Furthermore, examples of constituent units (b-2) derived from monomers represented by formula (1-2) that constitute thermoplastic resin B2 include, for example, at least one constituent unit derived from 2,2'-([1,1'-binaphthalene]-2,2'-diyrbis(oxy))acetoacetic acid (BINOL-DC) and its methyl ester, ethyl ester, and phenyl ester.

[0047] Examples of thermoplastic resin C include, but are not limited to, the following: PC-3, PC-5, PC-6, etc.

[0048] Examples of thermoplastic resins D that include at least one constituent unit selected from the group consisting of general formulas (7) to (9) include aliphatic olefin resins such as COC (cycloolefin copolymer) and COP (cycloolefin polymer). Examples of such aliphatic olefin resins include, but are not limited to, APEL® manufactured by Mitsui Chemicals, Inc., Topas® manufactured by Polyplastics Co., Ltd., and ZEONEX® manufactured by Nippon Zeon Co., Ltd.

[0049] Specific examples of the constituent units represented by formula (10) include those derived from decahydro-1,4:5'8-dimethanonaphthalene-2-methoxycarbonyl-6(7)-methanols. Examples include structural units derived from compounds selected from decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6-methanol, decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-7-methanol, 2-methyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6-methanol, 2-methyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-7-methanol, 2-ethyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6-methanol, and 2-ethyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-7-methanol.

[0050] In one embodiment of the present invention, the thermoplastic resin D, if it includes a structural unit represented by formula (10), can be selected from polycarbonate resin, polyester resin, and polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin D including the structural unit represented by formula (10) includes polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin D including the structural unit represented by formula (10) includes polyester resin. In yet another embodiment of the present invention, the thermoplastic resin D including the structural unit represented by formula (10) includes polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin D including the structural unit represented by formula (10) is polycarbonate resin.

[0051] In some embodiments, thermoplastic resins B1, B2, and B3 may each contain a monomer-derived constituent unit (b-1) represented by formula (1-1), a monomer-derived constituent unit (b-2) represented by formula (1-2), or a monomer-derived constituent unit (b-3) represented by formula (1-3a), in addition to a monomer-derived constituent unit (b-4) represented by the following formula (1-4). In equation (1-4), G １ and G２ Each of these independently represents an alkylene group having 1 to 8 carbon atoms, which may have substituents, and K １ and K ２ Each of these independently represents a hydroxyl group, an alkoxy group, or a halogen atom, and R ｐ１ and R ｐ２ Each of these independently represents a halogen atom, a cyano group, or an alkyl group having 1 to 8 carbon atoms which may have substituents, Ar １ and Ar ２ Each independently represents a phenyl group or a naphthyl group which may have substituents, and r １ and r ２ Each of these independently represents an integer between 0 and 2, and r ３ and r ４ Each of these independently represents an integer between 0 and 1.

[0052] In equation (1-4), G １ and G ２ Each of these independently represents an alkylene group having 1 to 8 carbon atoms, which may have substituents. Examples of the alkylene groups having 1 to 8 carbon atoms include methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, pentylene, etc. Among these, G １ and G ２ The material is preferably methylene, ethylene, propylene, butylene, isobutylene, or sec-butylene; more preferably methylene, ethylene, or propylene; even more preferably methylene or ethylene; and particularly preferably ethylene.

[0053] In equation (1-4), K １ and K ２ Each of these independently represents a hydroxyl group, an alkoxy group, or a halogen atom. １ and K ２ If it is an alkoxy group, the number of carbon atoms is not particularly limited; for example, it can be an alkoxy group with 1 to 20 carbon atoms.

[0054] In equation (1-4), R ｐ１ and R ｐ２Each of these independently represents a halogen atom, a cyano group, and an alkyl group having 1 to 8 carbon atoms, which may have substituents. In formula (1-4), Ar １ and Ar ２ Each independently represents a phenyl group or a naphthyl group which may have substituents. In formula (1-4), r １ and r ２ Each of these independently represents an integer between 0 and 2, preferably between 0 and 1. Also, in equation (1-4), r ３ and r ４ Each of these independently represents an integer between 0 and 1.

[0055] In formula (1-4), the substituents that "may have substituents" are not particularly limited, but examples include halogen atoms, hydroxyl groups, carboxyl groups, cyano groups, etc. These substituents may be present individually or in combination of two or more types.

[0056] In some embodiments, the thermoplastic resin preferably comprises a resin having at least one structural unit selected from the group consisting of the following general formulas (1-4a) to (1-4c). General formula (1-4a) is 9,9-bis(carboxyalkyl)fluorenes, and in the above formula (1-4), r ３ and r ４ It is a monomer-derived constituent unit where 0. The general formula (1-4b) is 9,9-bis(carboxyalkyl)-diarylfluorenes, and r ３ and r ４ is 1, and Ar １ and Ar ２ It is a monomer-derived structural unit in which the phenyl group is. The general formula (1-4c) is 9,9-bis(carboxyalkyl)-dinaphthylfluorenes, and r ３ and r ４ is 1, and Ar １ and Ar ２ It is a constituent unit derived from a monomer that has a naphthyl group.

[0057] In the above formulas (1-4a), (1-4b), and (1-4c), G １ and G ２ , R ｐ１and R ｐ２ , r １ and r ２ This is the same as the definition in equation (1-4).

[0058] Specific examples of monomers that derive the constituent units represented by formula (1-4a) include 9,9-bis(carboxyC2-6alkyl)fluorenes, preferably 9,9-bis(carboxyC2-4alkyl)fluorenes, more preferably 9,9-bis(carboxyC2-3alkyl)fluorenes, as well as their alkyl esters and acid halides. For example, 9,9-bis(2-carboxyethyl)fluorene, 9,9-bis(2-carboxypropyl)fluorene, as well as their alkyl esters and acid halides, preferably 9,9-bis(2-carboxyethyl)fluorene, as well as its alkyl esters and acid halides. The alkyl group in the case of an alkyl ester is not particularly limited and is, for example, an alkyl group having 1 to 20 carbon atoms.

[0059] Specific examples of monomers that derive the constituent units represented by formula (1-4b) include 9,9-bis(carboxyC2-6alkyl)-diphenylfluorenes, preferably 9,9-bis(carboxyC2-4alkyl)-diphenylfluorenes, more preferably 9,9-bis(carboxyC2-3alkyl)-diphenylfluorenes, as well as their alkyl esters and acid halides. For example, 9,9-bis(2-carboxyethyl)-1,8-diphenylfluorene, 9,9-bis(2-carboxyethyl)-2,7-diphenylfluorene, 9,9-bis(2-carboxyethyl)-3,6-diphenylfluorene, 9,9-bis(2-carboxyethyl)-4,5-diphenylfluorene, 9,9-bis(2-carboxypropyl)-2,7-diphenylfluorene, as well as their alkyl esters and acid halides. In the case of alkyl esters, the alkyl group is not particularly limited and is, for example, an alkyl group having 1 to 20 carbon atoms.

[0060] Specific examples of monomers that derive the constituent units represented by formula (1-4c) include constituent units derived from 9,9-bis(carboxyC2-6alkyl)-dinaphthylfluorenes. In this case, the compound that derives the constituent units may be an alkyl ester, an acid halide, or an acid anhydride. Examples of constituent units include compounds selected from 9,9-bis(2-carboxyethyl)-1,8-di(2-naphthyl)fluorene, 9,9-bis(2-carboxyethyl)-2,7-di(2-naphthyl)fluorene, 9,9-bis(2-carboxyethyl)-3,6-di(2-naphthyl)fluorene, 9,9-bis(2-carboxyethyl)-4,5-di(2-naphthyl)fluorene, 9,9-bis(2-carboxypropyl)-2,7-di(2-naphthyl)fluorene, 9,9-bis(2-carboxyethyl)-2,7-di(1-naphthyl)fluorene, their alkyl esters, and acid halides. The alkyl group in the case of an alkyl ester is not particularly limited and is, for example, an alkyl group having 1 to 20 carbon atoms.

[0061] In some embodiments, the constituent unit (b-4) includes constituent units derived from 9,9-bis(2-carboxyethyl)fluorene, its C1-C20 (preferably C1-C8, more preferably C1-C6) alkyl ester, and acid halides. In certain embodiments, the constituent unit (b-4) includes constituent units derived from 9,9-bis(2-carboxyethyl)fluorene.

[0062] Specific examples of the constituent units represented by formula (1-4) include 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (also called "BCFL"), 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (also called "BPEF"), 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9'9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, and 9,9-bis[4-(2-hydroxyethoxy)-3-t [ert-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (also known as "BPEF"), bisphenol A (also known as "BPA"), bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bis(4-hydroxyphenyl)-2 ,2-dichloroethylene, bisphenol E, bisphenol F, bisphenol G, bisphenol M (also called "BPM"), bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, bisphenol P-AP (4,4'-(1-phenylethylidene)bisphenol), bisphenol P-CDE (4,4'-cyclododecylidenebisphenol), bisphenol P-HTG (4,4'-(3,3,5-trimethylcyclohexylidene)bisphenol), bisphenol P-MIBK (4,4'-( 1,3-dimethylbutylidene)bisphenol), bisphenol PEO-FL (bisphenoxyethanol fluorene), bisphenol P-3MZ (4-[1-(4-hydroxyphenyl)-3-methylcyclohexyl]phenol), bisphenol OC-FL (4,4'-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol), bisphenol Z, BP-2EO (2,2'-[1,1'-biphenyl]-4,4'-diylbis(oxy)bisethanol), S-BOC (4,Examples of constituent units include those derived from 4'-(1-methylethylidene)bis(2-methylphenol), TrisP-HAP(4,4',4''-ethylidenttrisphenol), etc.

[0063] In one embodiment, the constituent units represented by formula (1-4) are constituent units derived from compounds selected from 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (BPEF).

[0064] In one embodiment, the thermoplastic resin mixture comprises a thermoplastic resin C containing only the monomer-derived constituent unit (c) represented by the general formula (2) above, and a resin T containing constituent units derived from naphthalenedicarboxylic acid, terephthalic acid, and their derivatives.

[0065] The resin T mentioned above may be, but is not limited to, a polyester obtained from BPEF (bisphenoxyethanol fluorene, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene) and naphthalenedicarboxylic acid, or a polyester carbonate obtained from BPEF, terephthalic acid, and dipropionic acid fluorene.

[0066] In the present invention, the resin composition may be a resin composition that is discharged after molding, such as a spool or runner, or it may be an unused or used resin composition.

[0067] In one embodiment of the present invention, the thermoplastic resin B may be selected from polycarbonate resin, polyester resin, and polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin B includes polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin B includes polyester resin. In yet another embodiment of the present invention, the thermoplastic resin B includes polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin B is polycarbonate resin.

[0068] In one embodiment of the present invention, the thermoplastic resin C may be selected from polycarbonate resin, polyester resin, and polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin C includes polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin C includes polyester resin. In yet another embodiment of the present invention, the thermoplastic resin C includes polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin C is polycarbonate resin.

[0069] In one embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C may be independently selected from polycarbonate resin, polyester resin, and polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C include polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C include polyester resin. In yet another embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C include polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C are polycarbonate resin.

[0070] 1-2. Fluorescence Spectrum Measurement Conditions In the detection step, a fluorescence spectrum is obtained by irradiating the thermoplastic resin with UV light. UV light (ultraviolet light) can be irradiated onto the thermoplastic resin using, for example, a known light source. The fluorescence spectrum obtained from the thermoplastic resin is then detected, for example, by a hyperspectral camera. In the detection step, it is preferable to irradiate the thermoplastic resin sample with UV light while it is resting on a black base. In this way, in the irradiation step in which UV light is irradiated, it is preferable to irradiate the thermoplastic resin sample directly with UV light. By using a sample with a black background, and by irradiating the sample directly with UV light, a clear fluorescence spectrum can be obtained.

[0071] Fluorescence spectrum data is obtained as a waveform showing the relationship between the wavelength and spectral intensity of fluorescence produced from a thermoplastic resin upon irradiation with UV light. The wavelength range in the fluorescence spectrum is, for example, 380 to 1000 nm, preferably 400 to 800 nm, or 400 to 700 nm.

[0072] The wavelength of the UV light irradiated onto the thermoplastic resin is, for example, 280 to 450 nm, preferably 300 to 400 nm, more preferably 330 to 390 nm, and particularly preferably around 365 nm, for example, 350 to 380 nm. Using UV light with such a wavelength range makes the differences in fluorescence spectra obtained from, for example, the above-mentioned plurality of thermoplastic resins B to D become significant, enabling efficient separation. Furthermore, there are no particular restrictions on the exposure time of the thermoplastic resin after irradiation with UV light, but it is determined according to, for example, the amount of thermoplastic resin sample. The exposure time is, for example, 30 seconds to 10 minutes, preferably 1 to 8 minutes, and more preferably 3 to 6 minutes. Note that the time for irradiating the thermoplastic resin with UV light can be very short, in accordance with conventional methods, and for example, a time in the millisecond range may be set.

[0073] 1-3. Forms and Methods for Sorting Thermoplastic Resins When the above measurement conditions are used, for example, the differences in fluorescence spectra obtained from the above-mentioned multiple thermoplastic resins B to D become significant, enabling efficient sorting. For example, thermoplastic resin B, which has a naphthalene ring, emits light when irradiated with UV light, but thermoplastic resins C, D, and T, which do not have a naphthalene ring, do not emit light or emit light weakly when irradiated with UV light. Therefore, the fluorescence spectra obtained between thermoplastic resin B and thermoplastic resins C, D, and T differ greatly, making sorting and separation easy.

[0074] Furthermore, by pulverizing a mixture containing multiple thermoplastic resins, and, for example, applying an air gun to the pulverized material that does not change color under UV irradiation, while not applying the air gun to the pulverized material that does change color under UV irradiation, it is possible to separate the pulverized material that does not change color under UV irradiation from the pulverized material that does change color under UV irradiation. While it may be possible to determine whether or not a material changes color under UV irradiation by visual inspection, it may also be done using the method described above.

[0075] For example, by crushing a mixture containing waste thermoplastic resins, spools, runners, and other scraps generated during the thermoplastic resin manufacturing process, and irradiating it with UV light to obtain a fluorescence spectrum, the types of resins in the mixture can be determined and identified, allowing for the separation of individual resins contained within the mixture. The separated thermoplastic resins can then be easily recycled and utilized. Furthermore, by obtaining fluorescence spectrum data from multiple resins contained in the mixture, it is possible to determine the content of a particular type of resin, for example, measuring the amount of contamination of a resin that was present in small quantities. Any detector can be used as long as it irradiates with UV light, compares it with a comparison color plate, records the position of the crushed material that glows or does not glow using a camera, and uses this position information to target the object to be removed with an air gun. Examples of such detectors include, but are not limited to, rheosorters.

[0076] The conditions for sorting by UV light can be set appropriately depending on the resin to be sorted. For example, the wavelength used for irradiation can be selected so that the resin to be sorted emits light, while impurity resins do not. The discharge rate, sensitivity, and conveyor belt speed of the UV sorter can also be set appropriately.

[0077] In a UV sorting machine, a comparison color plate may be used. For example, by using white paper that develops color under UV light, it is possible to utilize the fact that this white paper contains a fluorescent whitening agent and glows blue when irradiated with UV light. When a "glowing blue" is used as the base, the machine can be set to reject "non-glowing resins" in comparison to it. If no white paper is used, i.e., no comparison color plate is used, the base becomes a dark state, "black," and it is possible to reject materials that glow blue or do not glow (or glow weakly) when irradiated with UV light.

[0078] 1-4. Pretreatment Process In the method of the present invention, gravity separation utilizing the difference in specific gravity of multiple resins can be used as a pretreatment before the above-mentioned sorting. Examples of such pretreatments include, but are not limited to, a wind separation treatment method in which the crushed material is sorted by wind power, a method in which the crushed material is immersed in a liquid such as salt water or fresh water and separated according to the difference in specific gravity of the crushed material relative to the liquid, and a method in which the crushed material with different specific gravity is separated by applying a constant vibration to the crushed material. In particular, when the crushed material is fine powder or smooth, the sorting efficiency of the UV sorter can be improved by performing pretreatment.

[0079] Anemulation separation is a method of separating and recovering pulverized material in a separation device capable of generating a rotating airflow, by exposing the pulverized material to the airflow generated by the device. This separation method involves separating material that has a high specific gravity or a low specific surface area and falls naturally due to its own weight from material that has a low specific gravity or a high specific surface area and is lifted up by the airflow.

[0080] In this method, pulverized resin with a high specific gravity or low specific surface area falls naturally due to its own weight, while pulverized resin with a low specific gravity or high specific surface area is stirred up. This makes it possible to separate and recover the resin with a high specific gravity or low specific surface area from the resin with a low specific gravity or high specific surface area.

[0081] In this type of air separation, the same operation may be repeated on the same pulverized material. For example, the material that has fallen naturally may be further separated by air separation to increase the content of resin with a high specific gravity or low specific surface area in the recycled resin that has a high specific gravity or low specific surface area.

[0082] In a preferred embodiment of the present invention, the method of the present invention includes air separation treatment of the pulverized material. The air separation treatment may be performed once (one pass), or twice (two passes) or more times.

[0083] 1-5. Granulation process for reuse For example, when reusing crude recycled resin recovered from a mixture, it is preferable to granulate the crude recycled resin into pellets in order to facilitate handling during molding and other processes.

[0084] In the granulation process, it is preferable to plasticize the pulverized material using a melt blend before granulation. Examples of granulation equipment for plasticization and granulation include single-screw extruders, twin-screw extruders, and multi-screw extruders, but any known type can be used. The pellet shape is preferably cylindrical, spherical, or elliptical.

[0085] For granulation, it is preferable to extrude the plasticized recycled resin into strands, cool them in a water tank, and then cut them into pellets using a pelletizer. The pellets removed from the water tank are usually dried to remove any moisture adhering to the surface.

[0086] The crude recycled resin can be reused after sorting using UV light and, for example, pre-treatment. In this case, it is preferable to reuse the crude recycled resin after granulating it as described above.

[0087] Alternatively, the recovered crude recycled resin, after sorting using UV light, can be subjected to, for example, (i) a process to remove impurities, or (ii) a process to manufacture recycled resin.

[0088] 2. Selection Process In the selection process, one of several thermoplastic resins is selected based on the fluorescence spectrum detected in the detection process. When fluorescence spectra are obtained according to the measurement conditions described above, the obtained fluorescence spectra will differ depending on the type of thermoplastic resin, making it possible to identify and select a specific thermoplastic resin.

[0089] For example, the fluorescence spectrum of a predetermined thermoplastic resin standard is measured in advance, and this is compared with the fluorescence spectrum obtained by the detection step described above (comparison step). If these fluorescence spectra match, it can be determined that the thermoplastic resin targeted in the detection step is of the same type as the thermoplastic resin used as the standard. Therefore, by using such a comparison step, a desired thermoplastic resin can be identified and distinguished from a mixture containing two or more types of thermoplastic resins using a simple method. Furthermore, for example, in the case of a mixture containing thermoplastic resins for which fluorescence spectrum data has already been obtained, the fluorescence spectra of multiple thermoplastic resins contained in the mixture can be compared to identify the type of at least one of the thermoplastic resins.

[0090] In the comparison step, preferably, multiple fluorescence spectra obtained under common measurement conditions are compared. More preferably, in the comparison step, the wavelength values ​​of the peak tops in multiple fluorescence spectra obtained under common measurement conditions are compared. The wavelength values ​​of the peak tops can be read relatively easily from the fluorescence spectrum data. Alternatively, in the comparison step, waveforms representing the intensity and wavelength of the fluorescence spectra may be compared. Since the waveforms as fluorescence spectrum data are generally determined for each type of thermoplastic resin, it becomes possible to easily identify substantially all types of thermoplastic resins.

[0091] 3. Method for manufacturing recycled resin and recycling thermoplastic resin The sorting process described above can also be used to sort out thermoplastic resin contained in waste resin material. Waste resin material refers to waste material containing thermoplastic resin that has been recovered after being molded, and waste resin material includes not only products that have been discarded after being manufactured, but also scraps such as spools and runners that are molded during the manufacturing process.

[0092] By using waste resin material as the target for sorting in this invention, thermoplastic resin contained in the waste resin material can be efficiently sorted and recovered. Thus, there are no particular limitations on the type of thermoplastic resin sorted from the waste resin material, but it includes those listed in section 1-1. Thermoplastic Resins above. For example, by sorting and recovering these thermoplastic resins from the waste resin material as recycled resin, the recycling of thermoplastic resin becomes easily possible. In the method for producing recycled resin that regenerates thermoplastic resin derived from waste resin material, the above-described methods and processes, for example, those described in sections 1-2. Measurement Conditions for Fluorescence Spectrum to 2. Sorting Process above, can also be used. By utilizing these processes, thermoplastic resin can be efficiently regenerated from waste resin material.

[0093] Furthermore, the sorting method of the present invention can also be applied to the production of thermoplastic resin compositions, the production of recycled resin compositions, and the like. For example, a thermoplastic resin composition can be produced by adding secondary components such as resins and additives different from the sorted thermoplastic resin to the thermoplastic resin sorted by the above sorting method. Alternatively, a recycled resin composition may be produced by adding the above-mentioned secondary components to a thermoplastic resin sorted from waste resin material.

[0094] The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto. (Thermoplastic resins of Examples 1 to 7) Pellets of thermoplastic resins of Examples 1 to 7, each having a constituent unit represented by the following formulas (i) to (vii), were prepared. Samples of polycarbonate resin were used in Examples 1 to 5, and samples of polyolefin resin were used in Examples 6 and 7. (Measurement conditions for fluorescence spectra) The measurement conditions for the fluorescence spectra of the thermoplastic resin samples in Examples 1 to 7 are as follows: The thermoplastic resin samples were placed on a black cloth without overlapping, and a UV light source (365 nm) was irradiated from an oblique upward direction. The fluorescence spectrum generated from the sample was measured using a hyperspectral camera placed directly above the sample. • Hyperspectral camera: EVA Japan Co., Ltd., NH series hyperspectral camera (wavelength resolution: 5 nm) • UV light source: AS ONE Corporation, Handy UV lamp SLUV-6 • Measurement wavelength: 380-1000 nm

[0095] (Fluorescence Spectrum Measurement Results) For each example of resin pellets shown below, the fluorescence spectrum was detected in the wavelength range of 380 to 680 nm, and the wavelength at which the peak of the spectrum occurred was measured (measurement of standard samples). The wavelengths at which the peak of each example was measured are shown in Table 1.

[0096] As shown in Table 1, differences were observed in the peak top wavelengths in the measurement results for each example. Furthermore, even in examples where the peak top wavelength values ​​were roughly the same, a comparison of the waveforms showing the relationship between wavelength and spectral intensity in their fluorescence spectrum graphs revealed clear differences. In each example, a sample of the new product's thermoplastic resin and a sample of the same type of thermoplastic resin, which was recovered after molding and obtained as pulverized material (waste resin) through a pulverization process, were used. It was confirmed that similar results could be obtained between the sample of the new product's thermoplastic resin and the sample of the same type of pulverized thermoplastic resin.

[0097] The results from these examples suggest that fluorescence spectroscopy can be used to classify multiple thermoplastic resins. Specifically, for each sample in the examples containing thermoplastic resin (waste resin) obtained through a pulverization process, fluorescence spectra were measured under common measurement conditions. By comparing these spectra (peak top wavelength, waveform, etc.) with the measurement results of each standard, it was confirmed that the type of resin could be classified and identified. This sorting method makes it easy to identify or classify a predetermined type of resin from waste materials containing multiple thermoplastic resins using a simple method. Furthermore, utilizing this sorting method can lead to more efficient recycling of waste materials containing resins.

Claims

1. A method for sorting thermoplastic resins, comprising: a detection step of irradiating multiple types of thermoplastic resins with UV light and detecting the fluorescence spectrum emitted from the thermoplastic resins; and a sorting step of sorting one of the multiple thermoplastic resins based on the fluorescence spectrum.

2. The sorting method according to claim 1, further comprising a comparison step of comparing the detected fluorescence spectrum with the fluorescence spectrum of a standard sample measured in advance.

3. The sorting method according to claim 1, wherein the wavelength of the UV light is 300 to 400 nm.

4. The sorting method according to claim 1, wherein the fluorescence spectrum is detected by a hyperspectral camera in the detection step.

5. The sorting method according to claim 1, wherein in the detection step, the sample of the thermoplastic resin is placed on a black base and the UV light is directly irradiated onto the sample.

6. The sorting method according to claim 1, wherein the wavelength range of the fluorescence spectrum is 380 to 1000 nm.

7. The selection method according to claim 2, wherein the comparison step involves comparing the wavelength values ​​of the peak tops in a plurality of fluorescence spectra.

8. The sorting method according to claim 2, wherein in the comparison step, a plurality of waveforms showing the intensity and wavelength of the fluorescence spectrum are compared with one another.

9. A sorting method according to claim 1, wherein the thermoplastic resin that is the target of the detection step comprises at least one of the constituent units b to d represented by the following formulas, wherein the constituent unit b is selected from the group consisting of a monomer-derived constituent unit (b-1) represented by the following general formula (1-1), a monomer-derived constituent unit (b-2) represented by the following general formula (1-2), and a monomer-derived constituent unit (b-3) represented by the following general formula (1-3a), the constituent unit c comprises a monomer-derived constituent unit (c) represented by the following general formula (2), and the constituent unit d is selected from the group consisting of the following general formulas (7) to (10). [In general formula (1-1), R ａ and R ｂ Each of these independently comprises a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group comprising one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S; m and n each independently represent an integer from 0 to 5; and X represents a single bond, -O-, -S-, -SO-, -SO ２ A divalent group represented by -, -CO-, or any of the following general formulas (3) to (6), (In general formulas (3) to (6), R ９ and R １０ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or, R ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R[[ID=�]] １１ and R １２ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or, R １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; R １３ to R １６ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to {12} carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or, R １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; R １７ to R ２６ Each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms, and at least one of R １７ to R ２６ is an alkyl group having 1 to 3 carbon atoms.) A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. ] [In the general formula (1-2), R ａ and R ｂ Each of these independently comprises a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, an optionally substituted C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from O, N, and S, an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from the group consisting of R ｈ is an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 3 to 20 carbon atoms that may have substituents and contains one or more heterocyclic atoms selected from O, N, and S; X is a single bond or an optionally substituted fluorene group; A and B are each independently an optionally substituted alkylene group having 1 to 5 carbon atoms; m and n are each independently an integer from 0 to 6, preferably an integer from 0 to 3; a and b are each independently an integer from 0 to 10, preferably an integer from 1 to 3; R' and R'' are each independently selected from the group consisting of a hydroxyl group, a halogen atom, an optionally substituted alkoxy group having 1 to 20 carbon atoms, and an optionally substituted aryloxy group having 6 to 20 carbon atoms. [In general formula (1-3a), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted C1-C20 alkyl group, and an optionally substituted C6-C20 aryl group; R''' is a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ [wherein is a C6-C20 aryl group which may have substituents, or a C3-C20 heteroaryl group which contains one or more heterocyclic atoms selected from O, N, and S and may have substituents, and n is an integer from 0 to 6.] [In general formula (2), R ｃ and R ｄ Each of these independently comprises a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxy group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxy group, an optionally substituted C6-C20 aryl group, a optionally substituted C3-C20 heteroaryl group comprising one or more heterocyclic atoms selected from O, N, and S and optionally substituted, or an optionally substituted C6-C20 aryloxy group, and -C≡C-R ｈ Selected from, R ｈ represents an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 3 to 20 carbon atoms which may have substituents and include one or more heterocyclic atoms selected from O, N, and S, and p and q each independently represent an integer from 0 to 5, Y １ These are single bonds, -O-, -S-, -SO-, -SO ２ A divalent group represented by -, -CO-, or any of the following general formulas (3) to (6), (In general formulas (3) to (6), R ９ and R １０ Each independently represents hydrogen, halogen, optionally substituted C1-C20 alkyl group, optionally substituted C1-C5 alkoxy group, optionally substituted C6-C12 aryl group, optionally substituted C7-C17 aralkyl group, or optionally substituted C2-C15 alkenyl group, or R ９ and R １０ These elements bond to each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms; c represents an integer from 0 to 20; R １１ and R １２ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; R １３ to R １６ Each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 3 to 20 carbon atoms; R １７ to R ２６ Each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms, and at least one of R １７ to R ２６ is an alkyl group having 1 to 3 carbon atoms.) A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10.] [In General Formulas (7) to (10), X ｇ each independently represents an alkylene group having 1 to 10 carbon atoms, R ｊ , R ｋ , and R ｌ Each of these independently comprises a halogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C20 cycloalkoxy group, a substituted or unsubstituted C6-C20 aryl group, a C3-C20 heteroaryl group containing one or more heterocyclic atoms selected from substituted or unsubstituted O, N, and S, a substituted or unsubstituted C6-C20 aryloxy group, and -C≡C-R ｉ Selected from, R ｉ represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms containing one or more heterocyclic atoms selected from O, N, and S, p independently represents an integer of 0 or 1, q, r, and s independently represent an integer of 0 to 10, t represents an integer of 1 to 3, where q is 2 or greater and there are two R ｊ If present on an adjacent carbon atom, two R ｊ They may come together to form a ring structure, and r is 2 or more, and two R ｋ If present on an adjacent carbon atom, two R ｋ They may come together to form a ring structure, and s is 2 or more, and two R ｌ If present on an adjacent carbon atom, two R ｌ They may come together to form a ring structure, R ｍ R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ｇ [This represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.] 10. The sorting method according to claim 9, wherein the thermoplastic resin comprises at least one of thermoplastic resins B to D, the thermoplastic resin B comprises one or more selected from the group consisting of thermoplastic resin B1 containing a monomer-derived constituent unit (b-1) represented by the general formula (1-1), thermoplastic resin B2 containing a monomer-derived constituent unit (b-2) represented by the general formula (1-2), and thermoplastic resin B3 containing a monomer-derived constituent unit (b-3) represented by the general formula (1-3a), the thermoplastic resin C comprises a monomer-derived constituent unit (c) represented by the general formula (2), and the thermoplastic resin D comprises at least one constituent unit selected from the group consisting of the general formulas (7) to (10).

11. The constituent unit (b-3) is derived from a monomer represented by the following general formula (1-3), The sorting method according to claim 9, wherein in general formula (1-3), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have substituents, and an aryl group having 6 to 20 carbon atoms which may have substituents.

12. The sorting method according to claim 1, wherein the sorting step separates the thermoplastic resin contained in the waste resin material.

13. A method for producing recycled resin, comprising obtaining the thermoplastic resin as recycled resin from the waste resin material by the sorting method described in claim 12.

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