Method for determining quantity of thermoplastic resin

Abstract

Provided is a novel method that makes it possible to determine the quantity of a thermoplastic resin contained in a molded article.　An embodiment of the present invention provides a method for determining the quantity of a thermoplastic resin A contained in a molded article, said method comprising a step C1 and a step C2. Step C1 is for measuring, from a Raman scattering spectrum of the molded article, the intensity of a Raman scattering peak A which is attributed to the thermoplastic resin A. Step C2 is for referring to a calibration curve which indicates the correlation between the content ratio of the thermoplastic resin A and the intensity of the Raman scattering peak A, and calculating, from the intensity of the Raman scattering peak A measured in step C1, the content ratio of the thermoplastic resin A contained in the molded article.　Another embodiment of the present invention provides a method for determining the quantity of a thermoplastic resin A contained in molding waste, said method comprising a step A, a step B, and a step C. Step A is for pulverizing molding waste that comprises a thermoplastic resin to obtain a pulverized product. Step B is for molding the pulverized product to obtain a molded article. Step C is for determining the quantity of the thermoplastic resin A contained in the molded article.　Another embodiment of the present invention provides a method for producing a recycled resin, said method comprising said step A, said step B, said step C, and a step D. Step D is for obtaining a recycled resin from a raw material that contains said pulverized product (a) and / or a pulverized product (b) which is obtained by pulverizing said molded article.

Description

Method for quantifying thermoplastic resins

[0001] The present invention relates to a method for quantifying thermoplastic resins, and more particularly to a method for quantifying thermoplastic resins in molded waste products. Furthermore, it also relates to a method for producing recycled resins using this quantification method.

[0002] In recent years, concerns about the deterioration of the natural environment and the increase in waste generation have grown, and the movement to recycle plastic products has intensified in an effort to realize a circular economy.

[0003] Injection molding is a typical method for manufacturing plastic products. Specifically, it involves pouring heated and molten resin into a mold and cooling it to produce a plastic product (molded body) in a predetermined shape. In this process, depending on the injection molding method, molding waste may be generated along with the plastic product, originating from the passage of molten resin within the mold. For example, when obtaining a molded body, molding waste such as sprues, runners, excess parts called "ears" that occur at both ends of films or sheets, and off-spec products are generated. Such molding waste can be very large in the industrial production of plastic products, and recycling of molding waste is being considered.

[0004] For example, Patent Document 1 describes a method for manufacturing recycled thermoplastic resin molded products, which involves crushing sprue runners (molding waste) and / or defective products generated during the molding process of thermoplastic resin molded products, mixing them with new thermoplastic resin, and then using the resulting mixture to injection-molde thermoplastic resin molded products again.

[0005] Japanese Patent Publication No. 2006-256339

[0006] When recycling molded waste made from thermoplastic resins, the resulting waste is collected and recycled. Ideally, the waste should be collected by resin type, but the waste composition may contain a mixture of multiple resins. If recycled as is, the quality of the recycled resin may deteriorate. Quantitative analysis of the resins contained in the molded waste is expected to improve recycling efficiency and / or the quality of the recycled resin. However, quantitative analysis of resins requires measuring the weight of the separated resins and calculating their proportions. Calculating proportions based on weight is time-consuming and labor-intensive, and detailed analysis of resin types is difficult. In this situation, there is a need for a new method that can quantitatively analyze the thermoplastic resins contained in molded articles.

[0007] The present invention is, for example, as follows: [1] A method for quantifying thermoplastic resin A contained in a molded article, comprising: step C1 measuring the intensity of a Raman scattering peak A attributed to the thermoplastic resin A from the Raman scattering spectrum of the molded article; and step C2 calculating the content ratio of the thermoplastic resin A contained in the molded article from the intensity of the Raman scattering peak A measured in step C1, with reference to a calibration curve showing the correlation between the content ratio of the thermoplastic resin A and the intensity of the Raman scattering peak A. [2] The method according to [1], wherein the calibration curve is created by measuring the intensity of the Raman scattering peak A of a plurality of calibration curve molded articles obtained by molding resin compositions containing thermoplastic resin A at different known concentrations. [3] The method according to [1] or [2], wherein the Raman scattering peak A is measured with a higher intensity for the thermoplastic resin A than for thermoplastic resins other than the thermoplastic resin A. [4] The method according to any one of [1] to [3], comprising selecting a Raman scattering peak A based on the Raman scattering spectrum of a molded article containing the thermoplastic resin A during or before step C1. [5] The method according to any one of [1] to [4], wherein the thermoplastic resin A is at least one selected from polycarbonate resin, polyester resin, and polyester carbonate resin. [6] The method according to any one of [1] to [5], wherein the proportion of thermoplastic resin in the molded article is 70% by weight or more with respect to the total weight of the molded article. [7] The method according to any one of [1] to [6], wherein the thermoplastic resin A includes at least one constituent unit selected from monomer-derived constituent units (A) represented by the following general formula (1), monomer-derived constituent unit (B) represented by the following general formula (2), monomer-derived constituent unit (C) represented by the following general formula (3), monomer-derived constituent unit (D) represented by the following general formula (4), and monomer-derived constituent unit (E) represented by the following general formula (5). [In formula (1), R ａ and R ｂis, independently of each other, a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 carbon atoms which may have a substituent and contains one or more hetero ring atoms selected from O, N and S, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ selected from the group consisting of, R ｈ is an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 3 to 20 carbon atoms which may have a substituent and contains one or more hetero ring atoms selected from O, N and S, X is a single bond or represents a fluorene group which may have a substituent, A and B each independently represent an alkylene group having 1 to 5 carbon atoms which may have a substituent, m and n each independently represent an integer of 0 to 6, and a and b each independently represent an integer of 0 to 10.] [In formula (2), R ｃ and R ｄ 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 a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent, Y is a single bond, a fluorene group which may have a substituent, -CR ２１ R ２２ -, -S-, -S(=O)-, -(CH ２ ) ｒ -, -O-, -(CH ２ ) ｒ -(SiR ２３ R ２４ -O) ｓ -SiR ２３ R ２４ -(CH ２ ) ｒ -, and -CR ２５ R<-Ph-CR ２５ R ２６ - Selected from the group consisting of R ２１ , R ２２ , R ２３ , R ２４ , R ２５ and R ２６ Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have substituents, or an aryl group having 6 to 30 carbon atoms which may have substituents, or R ２１ and R ２２ , or R ２３ and R ２４ The terms represent a carbon ring or heterocycle having 1 to 20 carbon atoms, which may have substituents, formed by the bonding of these terms. Ph represents a phenyl group. r and s each independently represent an integer from 0 to 5000. A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have substituents. p and q each independently represent an integer from 0 to 4. a and b each independently represent an integer from 0 to 10. [In formula (3), 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 alkoxyl group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxyl 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 ｈis 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 a fluorene group that may have substituents; A and B each independently represent an alkylene group having 1 to 5 carbon atoms that may have substituents; m and n each independently represent an integer from 0 to 6; a and b each independently represent an integer from 0 to 10; R' and R'' each independently are selected from the group consisting of a hydroxyl group, a halogen atom, an alkoxy group having 1 to 20 carbon atoms that may have substituents, and an aryloxy group having 6 to 20 carbon atoms that may have substituents. [In formula (4), R ｇ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. [In formula (5), G １ and G ２ 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 ４Each of these independently represents an integer from 0 to 1. ] [8] The method according to [7], wherein the thermoplastic resin A is selected from the group consisting of a resin comprising the constituent unit (A) and the constituent unit (B), a resin comprising the constituent unit (B) and the constituent unit (C), a resin comprising the constituent unit (B) and the constituent unit (D), a resin comprising the constituent unit (A), a resin comprising the constituent unit (B), a resin comprising the constituent unit (C), and a resin comprising the constituent unit (D). [9] The method according to any one of [1] to [8], wherein the thermoplastic resin A is represented by any of the following formulas (I-1) to (I-14). (I-1) A resin containing a constituent unit represented by formula (i) (I-2) A resin containing a constituent unit represented by formula (iii) and a constituent unit represented by formula (v) (I-3) A resin containing a constituent unit represented by formula (ii), a constituent unit represented by formula (iii), and a constituent unit represented by formula (v) (I-4) A resin containing a constituent unit represented by formula (i) and a constituent unit represented by formula (iii) (I-5) A resin containing a constituent unit represented by formula (i) and a constituent unit represented by formula (vi) (I-6) A resin containing a constituent unit represented by formula (v), a constituent unit represented by formula (ii), and a constituent unit represented by formula (iii) (I-7) A resin containing a constituent unit represented by formula (ii), a constituent unit represented by formula (iii), and a constituent unit represented by formula (iv) (I-8) A resin containing a constituent unit represented by formula (v) (I-9) A resin containing a constituent unit represented by formula (i) and a constituent unit represented by formula (vii) (I-10) A resin containing a constituent unit represented by formula (ii) and a constituent unit represented by formula (vii) (I-11) A resin containing a constituent unit represented by formula (viiii), a constituent unit represented by formula (xi), a constituent unit represented by formula (x), and a constituent unit represented by formula (xi) (I-12) A resin containing a constituent unit represented by the following formula (viiii), a constituent unit represented by formula (ix), a constituent unit represented by formula (x), and a constituent unit represented by formula (xiiii) (I-13) A resin containing a constituent unit represented by the following formula (viiii), a constituent unit represented by formula (x), and a constituent unit represented by formula (xii) (I-14) A resin containing a constituent unit represented by formula (ii), a constituent unit represented by formula (iii), and a constituent unit represented by formula (xiv)

[10] A method for determining thermoplastic resin A contained in molded waste, comprising: step A, pulverizing molded waste made of thermoplastic resin to obtain pulverized material (a); step B, molding the pulverized material to obtain a molded body; and step C, determining the amount of thermoplastic resin A contained in the molded body, wherein step C is performed by the method described in any of [1] to [9].

[11] A method for producing recycled resin, comprising: step A, pulverizing molded waste made of thermoplastic resin to obtain pulverized material (a); step B, molding the pulverized material (a) to obtain a molded body; step C, determining the amount of thermoplastic resin A contained in the molded body; and step D, obtaining recycled resin from raw materials containing at least one of the pulverized material (a) and pulverized material (b) obtained by pulverizing the molded body, wherein step C is performed by the method described in any of [1] to [9].

[12] The method according to

[10] or

[11] , wherein the molded waste comprises a sprue portion and / or a runner portion, which are discharged after molding an optical material.

[13] The method according to

[11] or

[12] , further comprising adding a diester carbonate and / or a dihydroxy compound to the raw materials in step D and polymerizing them.

[14] The method according to

[11] or

[12] , further comprising adding a diester carbonate and / or a dihydroxy compound and an aryl alcohol to the raw materials in step D to prepare a reaction solution and polymerizing it.

[15] The method according to

[11] or

[12] , further comprising adding a diester carbonate and / or a dihydroxy compound and an aryl alcohol to the raw materials in step D to prepare a reaction solution, filtering it with a filter and then polymerizing it.

[0008] A novel method is provided for quantifying the thermoplastic resin contained in a molded article. The method of the present invention makes it possible to quantify the type of resin (resin content) contained in molded waste without laborious processes such as weighing separated resins. Furthermore, by using molded waste with quantified resin types as raw material, recycled resin can be produced with excellent recycling efficiency and / or high quality.

[0009] This figure shows the Raman scattering spectra of molded articles of calibration curve preparation resin compositions containing PC-2 and PC-3 at different resin ratios. The spectra were prepared in Calibration Curve Preparation Example 1 (Molding Method A, Raman Spectroscopy Method A) for PC-3 content and 1410 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak. Calibration curve creation example 1 (formulation method A, Raman spectroscopy method A) shows the correlation between the PC-3 content and 1375 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak. Calibration curve creation example 1 (formulation method A, Raman spectroscopy method A) shows the correlation between the PC-3 content and 1025 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak. Calibration curve creation example 2 (formulation method A, Raman spectroscopy method B) shows the correlation between the PC-3 content and 1375 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak. Calibration curve creation example 3 (formulation method A, Raman spectroscopy method B) shows the correlation between the PC-1 content and 1146 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak. Calibration curve creation example 2' (formulation method B, Raman spectroscopy method B) shows the correlation between the PC-3 content and 1375 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak. Calibration curve creation example 3' (formulation method B, Raman spectroscopy method B) shows the correlation between the PC-1 content and 1146 cm⁻¹. －１ This figure shows the correlation with the intensity of the Raman scattering peak.

[0010] The meanings of terms and other terms used in this specification will be explained below, and the present invention will be described in detail.

[0011] In this specification, "halogen atom" means fluorine atom (F), chlorine atom (Cl), bromine atom (Br), or iodine atom (I).

[0012] 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. Examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl groups.

[0013] Examples of 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, and pentyloxy groups.

[0014] Examples of 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.

[0015] Examples of 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. Examples of cycloalkyloxy groups having 5 to 10 carbon atoms include cyclopentyloxy, cyclohexyloxy, bicyclo[2.2.1]heptyloxy, and bicyclo[2.2.2]octyloxy.

[0016] Examples of aryl groups having 6 to 20 carbon atoms include phenyl, tolyl, xylyl, trimethylphenyl, tetramethylphenyl, ethylphenyl, ethylmethylphenyl, diethylphenyl, propylphenyl, isopropylphenyl, isopropylmethylphenyl, benzyl, phenethyl, phenylpropyl, naphthyl, anthracenyl, phenantrenyl, naphthacenyl, chrycerinyl, pyrenyl, biphenyl, terphenyl, and quaterphenyl groups.

[0017] Examples of heteroaryl groups having 3 to 20 carbon atoms and containing one or more heterocyclic atoms selected from O, N, and S include 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, naphthyridyl 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.

[0018] Examples of aryloxy groups having 6 to 20 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, anthracenyloxy group, phenantrenyloxy group, naphthacenyloxy group, chrycerinyloxy group, pyrenyloxy group, biphenyloxy group, terphenyloxy group, and quaterphenyloxy group.

[0019] Examples of alkyloxycarbonyl groups having 2 to 10 carbon atoms include methyloxycarbonyl group, ethyloxycarbonyl group, propyloxycarbonyl group, isopropyloxycarbonyl group, butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, and tert-butyloxycarbonyl group.

[0020] Examples of cycloalkyloxycarbonyl groups having 5 to 10 carbon atoms include cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group, bicyclo[2.2.1]heptyloxycarbonyl group, and bicyclo[2.2.2]octyloxycarbonyl group.

[0021] Examples of aryloxycarbonyl groups having 7 to 15 carbon atoms include phenyloxycarbonyl group, tolyloxycarbonyl group, xylyloxycarbonyl group, trimethylphenyloxycarbonyl group, tetramethylphenyloxycarbonyl group, ethylphenyloxycarbonyl group, ethylmethylphenyloxycarbonyl group, diethylphenyloxycarbonyl group, naphthyloxycarbonyl group, and others.

[0022] Examples of alkylcarbonyloxy groups having 2 to 10 carbon atoms include methylcarbonyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, and butylcarbonyloxy group.

[0023] Examples of cycloalkylcarbonyloxy groups having 5 to 10 carbon atoms include cyclopentylcarbonyloxy groups, cyclohexylcarbonyloxy groups, bicyclo[2.2.1]heptylcarbonyloxy groups, and bicyclo[2.2.2]octylcarbonyloxy groups.

[0024] Examples of arylcarbonyloxy groups having 7 to 15 carbon atoms include phenylcarbonyloxy group, tolylcarbonyloxy group, xylylcarbonyloxy group, trimethylphenylcarbonyloxy group, tetramethylphenylcarbonyloxy group, ethylphenylcarbonyloxy group, ethylmethylphenylcarbonyloxy group, diethylphenylcarbonyloxy group, naphthylcarbonyloxy group, and the like.

[0025] Examples of hydroxyalkylcarbonyl groups having 2 to 10 carbon atoms include hydroxymethylcarbonyl group, hydroxyethylcarbonyl group, and hydroxypropylcarbonyl group.

[0026] Examples of amide groups having 1 to 10 carbon atoms include methylaminocarbonyl group, ethylaminocarbonyl group, dimethylaminocarbonyl group, and acetylamino group.

[0027] 1. Method for Determining Thermoplastic Resin One embodiment of the present invention relates to a method for determining thermoplastic resin A contained in a molded article, comprising the following steps C1 and C2: Step C1: A step of measuring the intensity of the Raman scattering peak A attributed to the thermoplastic resin A from the Raman scattering spectrum of the molded article (peak intensity measurement step). Step C2: A step of calculating the content ratio of the thermoplastic resin A contained in the molded article from the intensity of the Raman scattering peak A measured in step C1, by referring to a calibration curve showing the correlation between the content ratio of the thermoplastic resin A and the intensity of the Raman scattering peak A (content calculation step).

[0028] Furthermore, one embodiment of the present invention relates to a method for quantifying thermoplastic resin A contained in molded waste. This quantification method includes the following steps A, B, and C. In the quantification method of this embodiment, step C has steps C1 and C2. Step A: A step of crushing molded waste made of thermoplastic resin to obtain crushed material (a) (crushing step) Step B: A step of molding the crushed material (a) to obtain a molded body (molding step) Step C: A step of quantifying the thermoplastic resin A contained in the molded body (quantification step) In this specification, "thermoplastic resin A" refers to the thermoplastic resin to be quantified.

[0029] This quantitative method is characterized by using Raman spectroscopy to quantitatively analyze multiple resins contained in molded waste products and molded articles made of thermoplastic resins. Specifically, the Raman scattering spectrum of the molded article is measured, and the content of thermoplastic resin A in the molded article is quantified from the intensity of Raman scattering peak A (a peak in the spectral region characteristic of thermoplastic resin A) attributed to thermoplastic resin A in the obtained spectrum and a calibration curve. The applicant has previously developed methods for separating waste resins using fluorescence emission such as ultraviolet light and Raman spectroscopy (e.g., PCT / JP2024 / 024866, PCT / JP2024 / 027061). Separation using fluorescence emission is a method of separating waste resins that emit fluorescence from those that do not by irradiating them with ultraviolet light. In order to quantify, it is necessary to measure the weight of the separated resins and calculate the ratio. However, this method is time-consuming and labor-intensive, has the problem that it cannot analyze detailed resin types, and cannot quantify resins that do not emit fluorescence, thus limiting its applicability. While Raman spectroscopy can be used to separate waste resins, a method for quantifying the resins themselves has not yet been established. This method allows for easy quantification of a wide range of thermoplastic resins without laborious steps such as weighing the separated resins.

[0030] 2. Method for Manufacturing Recycled Resin Another embodiment of the present invention relates to a method for manufacturing recycled resin. This manufacturing method includes the following steps A, B, C, and D. Step A: A step of crushing molded waste made of thermoplastic resin to obtain crushed material (a) (crushing step) Step B: A step of molding the crushed material (a) to obtain a molded body (molding step) Step C: A step of quantifying the thermoplastic resin A contained in the molded body (quantification step) Step D: A step of obtaining recycled resin from raw materials containing at least one of the crushed material (a) and the crushed material (b) obtained by crushing the molded body (recycled resin manufacturing step) In this embodiment of the manufacturing method, after step C, recycled resin is manufactured from raw materials containing the crushed material (a) of molded waste and the crushed material (b) of the molded body used for quantification. Steps A, B, and C are the same as those described in "1. Method for Quantifying Thermoplastic Resin" above. By using the raw materials after quantification, the molar ratio balance of the raw materials can be adjusted, which allows the polymerization reaction to proceed stably and enables the accurate acquisition of resins with desired physical properties. This allows for the production of high-quality recycled resins from molded waste with high recycling efficiency. The following describes "molded waste" and "thermoplastic resin," followed by a description of each process.

[0031] 3. Molding waste In this specification, molding waste refers to the part of a molded body generated during the molding process of thermoplastic resins that is not the final product (e.g., a plastic product). Therefore, molding waste is composed of thermoplastic resin. Molding waste may be composed of one type of thermoplastic resin or two or more types of thermoplastic resins. The type and combination of thermoplastic resins constituting the molding waste can be determined according to the physical properties of the desired plastic product (molded body).

[0032] In some embodiments, the molding waste is generated after the optical material has been molded. In some embodiments, the molding waste is generated after the optical lens has been molded.

[0033] In some embodiments, the molding waste includes sprue and / or runner portions. In one embodiment, the molding waste is discharged after molding optical materials (preferably optical lenses). The molding waste may include molding waste of different shapes.

[0034] In this specification, "sprue portion" means a portion having a shape derived from the sprue (flow channel of molten resin) within the mold. In this specification, "molten resin" refers to resin in a molten state. The shape of the sprue portion is not particularly limited, but it is preferably frustoconical. The inner diameter of the sprue portion varies depending on the physical properties of the molten resin used, the shape of the desired plastic product (molded article), etc., but is preferably 0.1 to 10 mm. In this specification, "inner diameter" means the maximum distance between two points on the contour line of a cross-section perpendicular to the longitudinal direction of the object. For example, if the shape of the sprue portion is frustoconical, its maximum inner diameter corresponds to the "inner diameter". The length of the sprue portion (corresponding to the height of the frustoconical if it is frustoconical) is preferably 0.1 to 200 mm.

[0035] In this specification, "runner portion" means a portion having a shape derived from the runner (flow channel of molten resin) in the mold. The shape of the runner portion is preferably cylindrical. The runner portion may also have a shape that branches in two or more directions, preferably two or three directions. The molten resin injected from the sprue may have a structure in which it flows in two or more directions by the branched runner. For this reason, the molded waste product may have two or more runner portions. It is more preferable to have three to thirty runner portions. The inner diameter of the runner portion varies depending on the physical properties of the molten resin used, the shape of the desired plastic product (molded product), etc., but is preferably 0.1 to 5 mm, more preferably 0.1 to 4 mm, and even more preferably 1 to 4 mm. The length of the runner portion (corresponding to the height of the cylinder if it is cylindrical) is preferably 0.1 to 200 mm.

[0036] Molding waste may contain, in addition to thermoplastic resin, other resins, additives, decomposition products thereof, etc. In this specification, "resin" means a resin with a weight-average molecular weight of 1000 or more. From the viewpoint of recycling efficiency and improving the quality of recycled resin, the content of thermoplastic resin in molding waste is, for example, 70% by weight or more, preferably 80% by weight or more, more preferably 85% by weight or more, even more preferably 90% by weight or more, even more preferably 95% by weight or more, even more preferably 99% by weight or more, and particularly preferably 100% by weight, based on the total weight of the molding waste.

[0037] 4. The thermoplastic resin constituting the thermoplastic resin molding waste is not particularly limited, but is preferably polyester resin, polycarbonate resin, polyester carbonate resin, epoxy resin, polyurethane resin, polyacrylic acid ester resin, polymethacrylic acid ester resin, etc., and is more preferably polycarbonate resin.

[0038] In some embodiments, the thermoplastic resin comprises at least one selected from monomer-derived structural units (A) represented by the following general formula (1), monomer-derived structural units (B) represented by the following general formula (2), monomer-derived structural units (C) represented by the following general formula (3), monomer-derived structural units (D) represented by the following general formula (4), and monomer-derived structural units (E) represented by the following general formula (5). In some embodiments, the thermoplastic resin comprises at least one selected from monomer-derived structural units (A) represented by the following general formula (1), monomer-derived structural units (B) represented by the following general formula (2), monomer-derived structural units (C) represented by the following general formula (3), and monomer-derived structural units (D) represented by the following general formula (4). In some embodiments, the thermoplastic resin comprises at least one selected from monomer-derived structural units (A) represented by the following general formula (1) and monomer-derived structural units (B) represented by the following general formula (2).

[0039] In some embodiments, the thermoplastic resin is a polycarbonate resin and includes at least one selected from the constituent units (A), (B), and (D).

[0040] In some embodiments, the thermoplastic resin is a polyester resin or a polyester carbonate resin and includes at least one selected from the constituent units (A), (B), (C), (D), and (E).

[0041] In some embodiments, the thermoplastic resin is a resin having structural unit (C) and / or structural unit (E). The resin is typically a resin (e.g., a polyester resin) that includes structural units derived from dihydroxy compounds (diols) along with structural unit (C) and / or structural unit (E). Examples of the dihydroxy compounds (diols) include structural units (A), structural unit (B), structural unit (D), and / or structural units derived from dihydroxy compounds (diols) represented by formulas (1), (2), and / or (4) above.

[0042] In some embodiments, the thermoplastic resin preferably includes at least one selected from the group consisting of a resin made of the constituent unit (A), a resin made of the constituent unit (A) and the constituent unit (B), a resin made of the constituent unit (B) and the constituent unit (C), a resin made of the constituent unit (B) and the constituent unit (D), a resin made of the constituent unit (A), a resin made of the constituent unit (B), a resin made of the constituent unit (C), and a resin made of the constituent unit (D). Such resins are excellent in terms of optical properties such as refractive index, and the optical properties of the recycled resin obtained by using the molded waste as a raw material can be improved.

[0043] (1) Constituent Unit (A) In some embodiments, the thermoplastic resin contains constituent units (A) derived from monomers represented by the following general formula (1). Constituent units (A) may be included individually or in combination of two or more types.

[0044] In equation (1), 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 alkoxyl group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxyl 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 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 ｂPreferably, it is 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 which may have substituents, and one or more heterocyclic atoms selected from O, N, and S; more preferably, it is a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have substituents, and even more preferably, it is a hydrogen atom, an aryl group having 6 to 12 carbon atoms which may have substituents.

[0045] In formula (1), X represents a fluorene group that is either a single bond or optionally has substituents. Preferably, X is a single bond or an optionally substituted fluorene group with a total of 12 to 20 carbon atoms.

[0046] In formula (1), A and B are each independently an alkylene group having 1 to 5 carbon atoms, which may have substituents, and are preferably an alkylene group having 2 or 3 carbon atoms.

[0047] In formula (1), m and n are each an integer between 0 and 6, preferably between 0 and 3, and more preferably 0 or 1.

[0048] In formula (1), a and b are each an integer between 0 and 10, preferably between 1 and 3, and more preferably 1 or 2.

[0049] In formula (1) above, the 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 cycloalkoxyl 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, and the like.

[0050] Specific examples of constituent unit (A) 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 "BNE"), 2,2'-bis(2-hydroxyethoxy)-6,6'-diphenyl-1,1'-binaphthalene (also referred to as "DP"), 9,9-bis[6-(2-hydroxyethoxy)naphthalene-2-yl]fluorene (also referred to as "BNEF"), 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene, and the like. In one embodiment, constituent unit (A) includes at least one of the constituent units derived from BNE, DP, and BNEF.

[0051] (2) Constituent Units (B) In some embodiments, the thermoplastic resin contains constituent units (B) derived from monomers represented by the following general formula (2). Constituent units (B) may be included individually or in combination of two or more types.

[0052] In equation (2), R ｃ and R ｄ Each of these is independently selected from the group consisting of a halogen atom, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C20 alkoxyl group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxyl group, and an optionally substituted C6-C20 aryl group. ｃ and R ｄ Preferably, it is 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 which may have substituents, and one or more heterocyclic atoms selected from O, N, and S; more preferably, it is a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have substituents, and even more preferably, it is a hydrogen atom, an aryl group having 6 to 12 carbon atoms which may have substituents.

[0053] In formula (2), Y represents a single bond, a fluorene group which may have a substituent, -CR ２１ R ２２ -, -S-, -S(=O)-, -(CH ２ ) ｒ -, -O-, -(CH ２ ) ｒ -(SiR ２３ R ２４ -O) ｓ -SiR ２３ R ２４ -(CH ２ ) ｒ -, and -CR ２５ R ２６ -Ph-CR ２５ R ２６ - and is selected from the group consisting of. Y is preferably a single bond or -CR ２１ R[[ID=3​​​​​​​​​​​​​​​​​​​​​​​​​​​​​In formula (2), a and b each independently represent integers from 0 to 10, preferably integers from 0 to 5, and more preferably integers from 0 to 2, such as 0 or 1.

[0057] In formula (2) above, the 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 cycloalkoxyl 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, and the like.

[0058] Specific examples of the constituent unit (B) 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-(2-hydroxyethoxy)-3-phenylphenyl)fluorene (also called "BPEF"), 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, and 9,9-bis[4-(2-hydroxyethoxy) [Xy)-3-tert-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 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 known as "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 Bisphenol 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 (4,4'-(1-methylethylidene)bis(2-methylphenol),) TrisP-HAP (4,4',Examples include those derived from 4''-ethylidene tris-phenol). In one embodiment, the structural unit (B) includes at least one of the structural units derived from BPPEF, BPPPEF, BPA, BPM, and BCFL.,

[0059] (3) Structural unit (C) In some embodiments, the thermoplastic resin includes a structural unit derived from a monomer represented by the following general formula (3). The structural unit (C) may be included alone or in combination of two or more.,

[0060]

[0061] In formula (3), R ａ and R ｂ are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 carbon atoms which may have a substituent and contains one or more hetero ring atoms selected from O, N and S, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ selected from the group consisting of. R ｈ represents an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 3 to 20 carbon atoms which may have a substituent and contains one or more hetero ring atoms selected from O, N and S. R ａ and R ｂ are preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 carbon atoms which may have a substituent and contains one or more hetero ring atoms selected from O, N and S, more preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms which may have a substituent, and still more preferably a hydrogen atom, an aryl group having 6 to 12 carbon atoms which may have a substituent.,

[0062] In formula (3), X represents a fluorene group that is either a single bond or may have substituents. Preferably, X is a single bond or a fluorene group that may have substituents with a total of 12 to 20 carbon atoms.

[0063] In formula (3), A and B are each independently an alkylene group having 1 to 5 carbon atoms, which may have substituents, and are preferably an alkylene group having 2 or 3 carbon atoms.

[0064] In formula (3), m and n are each an integer between 0 and 6, preferably between 0 and 3, and more preferably 0 or 1.

[0065] In formula (3), a and b are each an integer between 0 and 10, preferably between 1 and 3, and more preferably 1 or 2.

[0066] In formula (3), R' and R'' are each independently selected from the group consisting of a hydroxyl group, a halogen atom, an optionally substituted C1-C20 alkoxy group, and an optionally substituted C6-C20 aryloxy group. R' and R'' are preferably a hydroxyl group, a C1-C5 linear alkoxy group, and a C6-C10 aryloxy group, and more preferably a hydroxyl group, a methoxy group, an ethoxy group, and a phenyloxy group.

[0067] In formula (3) above, the substituents in the case where "may have substituents" are not particularly limited, but examples include halogen atoms, C1-C10 alkyl groups, C5-C10 cycloalkyl groups, C1-C10 alkoxy groups, C5-C10 cycloalkoxyl 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, and the like.

[0068] Specific examples of constituent unit (C) include those derived from 2,2'-([1,1'-binaphthalene]-2,2'-diyrbis(oxy))acetoacetic acid (BINOL-DC) and its methyl ester, ethyl ester, phenyl ester, etc. In one embodiment, constituent unit (C) includes at least one constituent unit derived from BINOL-DC and its methyl ester, ethyl ester, or phenyl ester.

[0069] (4) Constituent Units (D) In ​​some embodiments, the thermoplastic resin contains constituent units (D) derived from monomers represented by the following general formula (4). Constituent units (D) may be included individually or in combination of two or more types.

[0070] In equation (4), R ｇ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Examples of alkyl groups having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Of these, R ｇ Each of these is preferably a hydrogen atom.

[0071] Specific examples of constituent units (D) include those derived from decahydro-1,4:5,8-dimethanonaphthalenediols (also referred to as "D-NDM"). For example, those derived from (decahydro-1,4:5,8-dimethanonaphthalene-2,6-diyl)dimethanol, (decahydro-1,4:5,8-dimethanonaphthalene-2,7-diyl)dimethanol, (2-methyldecahydro-1,4:5,8-dimethanonaphthalene-2,6-diyl)dimethanol, (2-methyldecahydro-1,4:5,8-dimethanonaphthalene-2,7-diyl)dimethanol, (2-ethyldecahydro-1,4:5,8-dimethanonaphthalene-2,6-diyl)dimethanol, (2-ethyldecahydro-1,4:5,8-dimethanonaphthalene-2,7-diyl)dimethanol, etc. In one embodiment, the constituent unit (D) includes at least one constituent unit derived from D-NDM.

[0072] (5) Constituent Units (E) In some embodiments, the thermoplastic resin contains constituent units (E) derived from monomers represented by the following general formula (5). Constituent units (E) may be included individually or in combination of two or more types.

[0073] In equation (5), 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.

[0074] In equation (5), 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.

[0075] In equation (5), R ｐ１ and R ｐ２ Each 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 (5), Ar １ and Ar ２ Each independently represents a phenyl group or a naphthyl group, which may have substituents. In formula (5), r １ and r ２ Each of these independently represents an integer between 0 and 2, preferably between 0 and 1. In equation (5), r ３ and r ４ Each of these independently represents an integer between 0 and 1.

[0076] In formula (5) above, 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.

[0077] 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 (5-1) to (5-3). General formula (5-1) is 9,9-bis(carboxyalkyl)fluorenes, and in the above formula (5), r ３ and r ４ It is a monomer-derived constituent unit where 0. The general formula (5-2) 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 (5-3) 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.

[0078] In the above equations (5-1), (5-2), and (5-3), G １ and G ２ , R ｐ１ and R ｐ２ ,r １ and r ２ This is the same as the definition in equation (5).

[0079] Specific examples of monomers that derive the constituent unit represented by formula (5-1) include 9,9-bis(carboxyC2-6 alkyl)fluorenes, preferably 9,9-bis(carboxyC2-4 alkyl)fluorenes, more preferably 9,9-bis(carboxyC2-3 alkyl)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. 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.

[0080] Specific examples of monomers that derive the constituent unit represented by formula (5-2) 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.

[0081] Specific examples of monomers that derive the constituent units represented by formula (5-3) 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.

[0082] In some embodiments, the constituent unit (E) 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 (E) includes constituent units derived from 9,9-bis(2-carboxyethyl)fluorene.

[0083] The above-mentioned constituent units (A), (B), (C), (D), and (E) may be included individually in the resin, or in combination of two or more types.

[0084] (6) Other constituent units The thermoplastic resin may further contain other polycarbonate resin constituent units in addition to the constituent units described above, or it may further contain other resin constituent units such as polyester resin, polyester carbonate resin, or polyolefin resin.

[0085] For example, other constituent units of polycarbonate resins include those derived from dihydroxy compounds (diols) such as alkylene glycols like ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, neopentyl glycol, and octylene glycol.

[0086] Furthermore, examples of constituent units for polyester resin or polyester carbonate resin include constituent units derived from dicarboxylic acids or their ester derivatives, such as terephthalic acid, naphthalenedicarboxylic acid, 9H-fluorene 9,9-dipropionic acid or its monoalkyl (methyl, ethyl, propyl, isopropyl, butyl) ester derivatives or dialkyl ester derivatives (e.g., 9,9-di(2-methoxycarbonylethyl)fluorene, 9,9-di(2-carboxyethyl)fluorene), 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, 2,2'-bis(carboxyethoxy)-1,1'-binaphthyl, 2,2'-bis(carboxyphenoxy)-1,1'-binaphthyl, and compounds represented by the following formula. Furthermore, examples of constituent units derived from dihydroxy compounds (diols) that constitute polyester resin or polyester carbonate resin include 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethane-1-ol)(DBHBNABHP; spiroglycol(3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, SPG); bisphenol TMC; bisphenol A; and alkylene glycols such as ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, neopentyl glycol, and octylene glycol, which are constituent units derived from dihydroxy compounds (diols).

[0087] In some embodiments, the content of these other constituent units is preferably as low as possible, for example, preferably 50% by weight or less, more preferably 30% by weight or less, and even more preferably 10% by weight or less, relative to the total weight of the thermoplastic resin constituting the molded waste.

[0088] In some embodiments, the content of the thermoplastic resin, which includes at least one selected from the constituent units (A), (B), (C), (D), and (E), is preferably 70% by weight or more, more preferably 80% by weight or more, and even more preferably 80 to 99% by weight, based on the total weight of the molded waste. When the resin content is 70% by weight or more, the quantitative accuracy of thermoplastic resin A can be improved. Furthermore, the recycling efficiency in the production of recycled resin can be improved.

[0089] Specific examples of resins containing the above constituent units (A) to (D) are described, for example, in International Publication Nos. WO2018 / 016516, WO2014 / 073496, WO2019 / 044875, WO2023 / 100778, WO2024 / 171914, and WO2016 / 052370, and can be preferably used in the present invention.

[0090] In some embodiments, the thermoplastic resin constituting the molding waste and / or the thermoplastic resin is represented by any of the following formulas (I-1) to (I-14). Furthermore, it is preferable that the thermoplastic resin constituting the molding waste is also represented by any of the following formulas (I-1) to (I-14). Such resins are excellent in terms of optical properties such as refractive index. When formulas (I-1) to (I-14) are not homopolymers, the proportion of each constituent unit (monomer ratio) is not particularly limited and may be any proportion. For example, each constituent unit is included in a proportion of 1 mol% to 100 mol% relative to the total constituent units (100 mol%) constituting the thermoplastic resin. (I-1) A resin containing the constituent unit represented by formula (i) (preferably polycarbonate resin, polyester carbonate resin, particularly preferably polycarbonate resin) (I-2) A resin containing the constituent unit represented by formula (iii) and the constituent unit represented by (v) (preferably polycarbonate resin, polyester carbonate resin, particularly preferably polycarbonate resin) (for example, molar ratio [(iii) / (v)] = 1 / 99 to 99 / 1, preferably 10 / 90 to 90 / 10, more preferably 30 / 70 to 70 / 30) (I-3) A resin containing the constituent units represented by formula (ii), formula (iii), and formula (v) (preferably polycarbonate resin, polyester carbonate resin, particularly preferably polycarbonate resin) (for example, molar ratio [(ii) / (iii)] = 1 / 99 to 99 / 1, preferably 10 / 90 to 90 / 10, more preferably 40 / 60 to 60 / 40) (I-4) A resin containing the constituent units represented by formula (i) and formula (iii) (preferably polycarbonate resin, polyester carbonate resin, particularly preferably polycarbonate resin) (for example, molar ratio [(i) / (iii)] = 1 / 99 to 99 / 1, preferably 10 / 90 to 90 / 10, more preferably 30 / 70 to 70 / 30 by weight) (I-5) A resin (preferably polycarbonate resin) containing the constituent units represented by formula (i) and (vi) (for example, molar ratio [(i) / (vi)] = 1 / 99 to 99 / 1, preferably 10 / 90 to 90 / 10, more preferably 40 / 60 to 60 / 40 by weight)(I-6) A resin containing the constituent units represented by formula (v), formula (ii), and formula (iii) (preferably polycarbonate resin) (for example, molar ratio [(v) / (ii) / (iii)] = 1 to 98 / 1 to 98 / 1 to 98, preferably 10 to 40 / 10 to 40 / 30 to 70) (I-7) A resin containing the constituent units represented by formula (ii), formula (iii), and formula (iv) (preferably polycarbonate resin) (for example, molar ratio [(ii) / (iii)] = 1 / 99 to 99 / 1, preferably 10 / 90 to 90 / 10, more preferably 40 / 60 to 60 / 40) (I-8) A resin containing the constituent units represented by formula (v) (preferably polycarbonate resin, polyester carbonate resin, particularly preferably polycarbonate resin) (I-9) A resin containing the constituent units represented by formula (i) and formula (vii) (preferably polycarbonate resin, polyester carbonate resin, particularly preferably polycarbonate resin) (for example, molar ratio [(i) / (vii)] = 1 / 99 to 99 / 1, preferably 10 / 90 to 90 / 10, more preferably 40 / 60 to 60 / 40%) (I-10) A resin containing the constituent units represented by formula (ii) and formula (vii) (preferably polycarbonate resin, polyester resin, polyester carbonate resin, particularly preferably polyester carbonate resin) (for example, molar ratio [(ii) / (vii)] = 10 / 90 to 90 / 10) (I-11) A resin containing a constituent unit represented by formula (viiii), a constituent unit represented by formula (ix), a constituent unit represented by formula (x), and a constituent unit represented by formula (xi) (preferably polyester carbonate resin, polyester resin, particularly preferably polyester carbonate resin) (for example, molar ratio [(vi) / (ix) / (xi)] = 1 to 98 / 1 to 98 / 1 to 98) (I-12) A resin containing a constituent unit represented by the following formula (viiii), a constituent unit represented by formula (ix), a constituent unit represented by formula (x), and a constituent unit represented by formula (xiiii) (preferably polyester carbonate resin, polyester resin, particularly preferably polyester carbonate resin) (for example, molar ratio [(viiii) / (ix) / (xiiii)] = 1 to 98 / 1 to 98 / 1 to 98)(I-13) A resin containing the constituent units represented by formula (viiii), formula (x), and formula (xii) below (preferably polyester carbonate resin, polyester resin, particularly preferably polyester carbonate resin) (for example, molar ratio [(viiii) / (x) / (xii)] = 1 to 98 / 1 to 98 / 1 to 98) (I-14) A resin containing the constituent units represented by formula (ii), formula (iii), and formula (xiv) (preferably polyester carbonate resin) (for example, molar ratio [(ii) / (iii) / (xiv)] = 1 to 98 / 1 to 98 / 1 to 98)

[0091] In some embodiments, the thermoplastic resin includes a polycarbonate resin comprising at least one constituent unit selected from the constituent units represented by formula (i), formula (ii), formula (iii), and formula (v). The ratio of each constituent unit is not particularly limited. Other constituent units may also be included.

[0092] The weight-average molecular weight (Mw) of the thermoplastic resin containing at least one selected from the constituent units (A), (B), (C), (D), and (E) is not particularly limited, but is preferably 10,000 to 70,000, and more preferably 15,000 to 50,000. A weight-average molecular weight (Mw) of 10,000 or more is preferable because it can maintain appropriate strength as a molded article, such as a resin for optical lenses. On the other hand, a weight-average molecular weight (Mw) of 70,000 or less is preferable because it can maintain appropriate fluidity during resin molding and improve moldability. In this specification, "weight-average molecular weight (Mw)" means the weight-average molecular weight on a polystyrene basis determined by gel permeation chromatography (GPC).

[0093] 5. Additives and Decomposition Products The additives constituting the molding waste are not particularly limited, and known additives may be used. Examples of resin decomposition products constituting the molding waste include monomers, dimers, copolymers, oligomers of resins or impurity resins having at least one constituent unit (A) to (E) selected from the group consisting of general formulas (1) to (5), aryl alcohols such as phenol, diesters of carbonates such as diphenyl carbonate, monomer modified products such as the following formulas (A-1) and (A-2), and resin modified products having substructures represented by the following formulas (B-1) and (B-2). In formulas (B-1) and (B-2), * indicates a bonding site.

[0094] 6. Process A: Grinding Process Process A is a process of grinding molded waste made of thermoplastic resin to obtain pulverized material (a). By grinding the molded waste, it can be made into a shape suitable for molding. Furthermore, since a homogeneous molded body is obtained in process B (molding process), the accuracy of quantitative measurement in process C (quantification process) is improved. In addition, by grinding and mixing to create a uniform blend, foreign matter is also uniformly dispersed, which has the advantage of allowing subsequent processes to proceed stably (uniformity of foreign matter amount). From the viewpoint of moldability, the average particle size of the pulverized material is preferably 0.1 to 5 mm, more preferably 0.5 to 5 mm, even more preferably 1 to 4 mm, and particularly preferably 2.5 to 4 mm. In this specification, "average particle size" means the average value of the diameter (maximum major axis) of the pulverized material, and can be measured, for example, by a particle size distribution analyzer.

[0095] The crushing method is not particularly limited, and any of the following methods may be used: compression, impact, shear, or friction.

[0096] Examples of crushers that can be used include coarse crushers such as jaw crushers, gyroscope crushers, impact crushers, single-shaft crushers, and twin-shaft crushers; medium crushers such as roll crushers, edge runners, disintegrators, SAG (Semi-Autogenous Grinding) mills, crushing rolls, hammer mills, and roller mills; and fine crushers such as bead mills, ball mills, vibrating ball mills, rod mills, jet mills, and planetary mills. Of these, it is preferable to use a coarse crusher, and more preferable to use a single-shaft or twin-shaft crusher. Specific examples of crushers include the high-power crushers 35-560, 35-720, 55-770, and 55-1050 (manufactured by Tanaka Co., Ltd.), and the low-speed crushers KGA-250 and KGA-350 (manufactured by Kawata Co., Ltd.). The above crushers may be used individually or in combination of two or more types.

[0097] 7. Process B: Molding Process Process B is a process of molding the pulverized material (a) to obtain a molded body. Molding is performed before measuring the Raman scattering spectrum, and quantification is performed based on the Raman scattering spectrum of the molded body, which is preferable because it allows for accurate analysis using the Raman scattering spectrum. The molding method is not particularly limited and can be any method, such as injection molding, high-speed injection molding, injection compression molding, two-color molding, hollow molding methods such as gas-assisted molding, molding using a heat-insulating mold, molding using a rapidly heated mold, foam molding (including supercritical fluid), insert molding, IMC (in-mold coating) molding, extrusion molding, sheet molding, thermoforming, rotational molding, lamination molding, press molding, compression molding, extrusion molding, and solution casting. Molding using a hot runner method can also be used. Among these, injection molding, extrusion molding, and press molding are preferred because they yield smooth molded pieces, and injection molding is even more preferred because it yields uniform molded pieces. The molding conditions when using the injection molding method are not particularly limited, but for example, from the viewpoint of molding stability, the cylinder temperature is in the range of 240 to 270°C (preferably 250 to 270°C), the feed rate is in the range of 10 to 20 kg / h (preferably 12 to 17 kg / h), the injection speed is in the range of 10 to 120 mm / s (preferably 50 to 100 mm / s), the screw rotation speed is in the range of 10 to 350 rpm (preferably 30 to 320 rpm, more preferably 30 to 200 rpm), and the back pressure is 0.1 to 10 MPa (preferably 0.5 to 5 MPa). The cylinder temperature refers to the temperature of the part of the injection molding machine that heats and melts the molding material.

[0098] The shape of the molded body is not particularly limited as long as it allows for measurement of the Raman scattering spectrum, but a plate-like shape is preferred because a smoother surface during measurement results in better analytical accuracy. The thickness of the molded body is preferably 1 to 5 mm, more preferably 2 to 4 mm, and even more preferably 2 to 3 mm, in order to allow the laser to pass through easily. The size (maximum diameter) of the molded body is preferably 70 to 150 mm, more preferably 80 to 120 mm, and even more preferably 80 to 90 mm.

[0099] 8. Process C: Quantitative process Process C is a process for quantifying the thermoplastic resin A contained in the molded article. As described above, process C comprises process C1 (peak intensity measurement process) and process C2 (content calculation process).

[0100] The proportion of thermoplastic resin in the molded article used for quantitative analysis is preferably 70% by weight or more, preferably 80% by weight or more, more preferably 85% by weight or more, even more preferably 90% by weight or more, even more preferably 95% by weight or more, even more preferably 99% by weight or more, and particularly preferably 100% by weight, based on the total weight of the molded article. The higher the proportion of thermoplastic resin, the better the quantitative accuracy can be. When the molded waste is crushed in step A and then molded as is in step B, the proportion of thermoplastic resin in the molded article will be the same as the proportion of thermoplastic resin in the molded waste. If the molded waste contains components other than thermoplastic resin, it is preferable to separate the molded waste or its crushed material (a) and adjust the proportion of thermoplastic resin in the molded waste or its crushed material (a) to be within the above range.

[0101] (8-1) Step C1: Peak intensity measurement step In step C1, the intensity of Raman scattering peak A, which is attributed to thermoplastic resin A, is measured from the Raman scattering spectrum of the molded body.

[0102] (i) Raman scattering spectrum measurement The Raman scattering spectrum is, for example, shown in Figure 1, with the horizontal axis representing wavenumber (cm²). －１ The vertical axis of the graph is obtained as the Raman scattering light intensity. The Raman scattering spectrum of the molded body can be measured using a Raman spectrometer. The apparatus used is not particularly limited, but for example, "Palmtop Raman PR-1w" (manufactured by JASCO Corporation) can be used. With a Raman spectrometer, laser light is irradiated onto the molded body, the Raman scattered light scattered from the molded body is spectrally separated in the spectroscopic unit, and the spectrally separated Raman scattered light is detected in the detection unit to obtain a Raman scattering spectrum. In this specification, the Raman scattering spectrum used is one measured at room temperature (e.g., 25°C).

[0103] (Laser Irradiation Conditions) The irradiation conditions for laser light in measuring Raman scattering spectra are not particularly limited. Irradiation conditions include, for example, laser wavelength, laser intensity, exposure time, and number of integrations. It is preferable to adjust these appropriately to obtain a Raman scattering spectrum with a high signal-to-noise ratio. The excitation wavelength of the laser light source is not particularly limited, but from the standpoint of difficulty in detecting fluorescence, the region of 700 to 900 nm is preferred, the region of 750 to 880 nm is more preferred, the region of 780 to 880 nm is even more preferred, and the region of 780 to 800 nm is particularly preferred. The laser intensity, exposure time, and number of integrations (exposures) are not particularly limited as long as the molded body is not damaged by the laser light. For example, the laser intensity can be gradually increased from a low level and adjusted appropriately to achieve high sensitivity within a range that does not damage the molded body. The exposure time and number of integrations (exposures) can be appropriately changed so that sufficient intensity of the Raman spectrum can be obtained with the laser intensity determined above. For example, the laser intensity is at a low level, the exposure time is preferably 3 to 10 seconds, more preferably 4 to 8 seconds, even more preferably 5 to 7 seconds, for example 5 or 7 seconds, and the number of cumulative (exposure) times is preferably 2 to 10 times, more preferably 3 to 9 times, even more preferably 4 to 8 times, for example 4 or 8 times.

[0104] (Background Correction) It is preferable to perform background correction (baseline correction) on the Raman scattering spectrum. Background correction is performed to remove the effects of background light that is thought to be caused by unavoidable light such as fluorescence, Rayleigh and Mie scattered light originating from the irradiation laser light, and disturbances other than the irradiation laser light. This is done by subtracting the background profile (baseline) obtained by fitting analysis using polynomial functions or spline functions from the peak profile described above. Background correction is preferably performed using analysis software attached to the Raman spectrometer (e.g., "JascoBackGroundData.BKG" (manufactured by JASCO Corporation)) under the same conditions (exposure time, number of integrations) as when measuring the sample, and by turning off the laser just before measuring the sample.

[0105] (Normalization of Raman Scattering Spectra) Since the intensity of Raman scattering spectra varies depending on the measurement, it is desirable to normalize the spectral data in order to establish a reference value for comparing the intensity of specific peaks. The normalization is 1606 cm⁻¹. －１ It is preferable to perform this by setting the intensity at the wavenumber to 1.

[0106] (ii) Analysis of Raman scattering spectrum: From the Raman scattering spectrum of the molded product, the intensity of Raman scattering peak A, which is attributed to thermoplastic resin A, is measured. In the Raman scattering spectrum, the horizontal axis is wavenumber (cm). －１ ), the vertical axis is obtained as the Raman scattering light intensity. In this specification, Raman scattering peak A refers to the Raman scattering peak attributed to thermoplastic resin A. In this specification, the intensity of a peak in the Raman scattering spectrum means the peak height in the Raman scattering spectrum. Raman scattering peak A can be selected based on the Raman scattering spectrum of a molded article containing thermoplastic resin A. It is preferable to select a peak with high intensity among the peaks attributed to thermoplastic resin A as Raman scattering peak A. By setting Raman scattering peak A to a peak measured with high intensity relative to thermoplastic resin A, highly accurate quantification becomes possible. Furthermore, it is even more preferable to set a peak measured with higher intensity relative to thermoplastic resin A than to thermoplastic resins other than thermoplastic resin A. By setting Raman scattering peak A to a peak measured with higher intensity relative to thermoplastic resin A compared to other thermoplastic resins, even higher accuracy quantification becomes possible. In some embodiments, Raman scattering peak A is a peak at a wavenumber where the peak intensity is preferably 2 times or more, more preferably 4 times or more, and even more preferably 6 times or more than, greater than 6 times greater compared to thermoplastic resin A. In some embodiments, the process includes selecting a Raman scattering peak A during or before step C1 based on the Raman scattering spectrum of the molded article containing the thermoplastic resin A. For example, a peak observed with high intensity for the thermoplastic resin A can be selected as the Raman scattering peak A from the Raman scattering spectrum obtained when creating a calibration curve, as described later.

[0107] For example, Figure 1 shows the Raman scattering spectra of molded articles of calibration curve preparation resin compositions containing thermoplastic resins PC-2 and PC-3 in different resin ratios. Taking the Raman scattering spectra shown in Figure 1 as an example, when the target for quantification is PC-2, PC-2 is measured with high intensity as the Raman scattering peak A of the thermoplastic resin A, which is the target for quantification, at 1001 cm⁻¹. -１ 1274cm -１ It is preferable to select peaks such as those mentioned above, and among them, the peak measured at a higher strength compared to PC-3, which is a thermoplastic resin other than thermoplastic resin A, is 1001 cm². -１ It is more preferable to select the peak at 1375 cm⁻¹, where PC-3 is measured with high intensity, as the Raman scattering peak A of the thermoplastic resin A that is the target of quantification. -１ , 1025cm -１ , 1410cm -１ , 1401cm -１ It is preferable to select peaks such as those mentioned above, and among them, 1410 cm is the peak that is measured with higher strength compared to PC-2, which is a thermoplastic resin other than thermoplastic resin A. -１ , 1375cm -１ , 1025cm -１ It is preferable to select peaks such as those mentioned above.

[0108] (iii) Identifying the type of thermoplastic resin The type of thermoplastic resin contained in the molded article may be identified during or before step C1. In some embodiments, the type of thermoplastic resin contained in the molded article is identified during step C1. In some embodiments, the type of thermoplastic resin contained in the molded article is identified using the Raman scattering spectrum of the molded article obtained in step C1. For example, Raman scattering information (Raman scattering information of a reference resin) obtained from the Raman scattering spectrum of a known resin to be identified is acquired, and the type of resin is identified by comparing the Raman scattering information of the reference resin with the Raman scattering spectrum of the molded article measured in step C1. In some embodiments, the type of thermoplastic resin contained in the molded article is identified before step C1. For example, the type of thermoplastic resin can be identified by analysis of the presence or absence of UV emission. By identifying the type of thermoplastic resin contained in the molded article during or before step C1, a calibration curve to be used in step C2 can be appropriately selected. Note that since molded waste is usually generated during the molding process of thermoplastic resin molded products, the type of resin mainly contained in the molded product can be inferred. In such cases, identification of the type of thermoplastic resin contained in the molded product can be omitted.

[0109] (3-2) Step C2: Peak Intensity Measurement Step C2 is a step in which the content of the thermoplastic resin A contained in the molded article is calculated from the intensity of the Raman scattering peak A measured in Step C1, by referring to a calibration curve that shows the correlation between the content of the thermoplastic resin A and the intensity of the Raman scattering peak A. In Step C2, the content (concentration) of the thermoplastic resin A contained in the molded article with an unknown mixing ratio is estimated from the intensity of the Raman scattering peak A measured in Step C1, using a calibration curve that shows the correlation between the content of the thermoplastic resin A and the intensity of the Raman scattering peak A.

[0110] (Calibration Curve) The calibration curve is not particularly limited, but it is preferable to create it by measuring the intensity of the Raman scattering peak A of a plurality of calibration curve molded bodies obtained by molding resin compositions containing thermoplastic resin A at different known concentrations. Specifically, it is preferable to produce calibration curve molded bodies by molding resin compositions containing thermoplastic resin A at different known concentrations, obtain the Raman scattering spectra of the calibration curve molded bodies, and create a calibration curve in advance that shows the correlation between the concentration of thermoplastic resin A and the Raman scattering peak intensity. For example, by creating a plurality of calibration curve molded bodies containing thermoplastic resin A and thermoplastic resins other than thermoplastic resin A at different mixing ratios, and obtaining the Raman scattering spectra for each molded body, a calibration curve showing the correlation between the concentration of thermoplastic resin A and the intensity of the Raman scattering peak A can be obtained. One type of thermoplastic resin other than thermoplastic resin A may be used as the thermoplastic resin included in the calibration curve molded body, or two or more types may be used.

[0111] In some embodiments, the calibration curve is prepared using a calibration curve molded body produced by the same molding method as the molded body used in step C1 to measure the intensity of Raman scattering peak A. In some embodiments, the calibration curve is prepared using the Raman scattering spectrum of a calibration curve molded body obtained under the same laser irradiation conditions as the Raman scattering spectrum of the molded body used in step C1 to measure the intensity of Raman scattering peak A. The intensity of the Raman scattering peak may vary depending on the molding method of the molded body, the laser irradiation conditions when obtaining the Raman scattering spectrum, and the thickness and shape of the molded body. Therefore, from the viewpoint of improving quantitative accuracy, it is preferable that the calibration curve molded body for preparing the calibration curve is measured by the same molding method as the molded body to be quantified (the molded body obtained in step B), and that the molding conditions are also the same. For example, when the molded body to be quantified is molded by injection molding, it is preferable that the molded body used for creating the calibration curve is also molded by the same injection molding method, and furthermore, it is preferable that it be molded under the same environmental conditions (for example, the same temperature conditions, pressure conditions, injection speed, screw rotation speed, and the same equipment). Note that the same temperature conditions, pressure conditions, injection speed, and screw rotation speed include cases where there is a variation of, for example, ±10%, preferably ±5%. Also, from the viewpoint of improving quantitative accuracy, it is preferable that the Raman scattering spectrum of the molded body for calibration is obtained under the same laser irradiation conditions as the Raman scattering spectrum measurement of the molded body to be quantified (the molded body obtained in process B). Specifically, it is preferable to use the same equipment and perform the molding and measurement under the same conditions.

[0112] By obtaining Raman scattering spectra from multiple calibration curve molded bodies with known compositions, a calibration curve can be created that shows a correlation between the content of thermoplastic resin A and the intensity of Raman scattering peak A.

[0113] Using this calibration curve, the content (concentration) of the thermoplastic resin A contained in the molded article can be calculated from the intensity of the Raman scattering peak A measured in step C1.

[0114] (1) Process D: Recycled resin manufacturing process Process D is a process of obtaining recycled resin from raw materials that include at least one of the pulverized material (a) obtained in process A and the pulverized material (b) obtained by pulverizing the molded body used for quantitative determination in process C.

[0115] The method for producing recycled resin is not particularly limited as long as recycled resin can be obtained from raw materials including pulverized material, and any known method can be used as appropriate. The recycled resin produced may be the same as or different from the resin contained in the molded waste.

[0116] For example, recycled resins are produced by polymerizing raw materials and, if necessary, dihydroxy compounds and / or diester carbonates in a reaction solvent, optionally in the presence of a catalyst. Some of the added dihydroxy compounds are incorporated into the resin as structural units through polymerization. Since diester carbonates form carbonate bonds through polymerization with dihydroxy compounds, it is particularly preferable to add diester carbonates when the thermoplastic resin contained in the raw materials includes at least one selected from polycarbonate resins and polyester carbonate resins.

[0117] In particular, it is preferable to prepare a reaction solution by dissolving the raw materials and, if necessary, a dihydroxy compound and / or diester carbonate in a reaction solvent, and then polymerize it. In some embodiments, the process for producing recycled resin includes adding an aryl alcohol to the raw materials to prepare a reaction solution and then polymerizing it. By polymerizing the raw materials while they are dissolved in the aryl alcohol in this way, excessive decomposition (depolymerization) of the resin components contained in the raw materials is suppressed, making it possible to efficiently produce recycled resin. In this specification, "reaction solution" refers to a solution in which the reactants are dissolved in a reaction solvent. In some embodiments, the process for producing recycled resin includes further adding a diester carbonate and / or a dihydroxy compound and an aryl alcohol to the raw materials to prepare a reaction solution, filtering it with a filter, and then polymerizing it. By filtering the reaction solution, foreign matter in the reaction solution is removed. Foreign matter includes, for example, metal materials, dust mixed in from the surroundings during molding, and unmelted material. Examples of unmelted material include unmelted material that occurs when waste resin contains resin components with low solubility in aryl alcohol (for example, olefin-based resins (e.g., cycloolefin polymer (COP) resins or cycloolefin copolymer (COC) resins)) that do not dissolve in the reaction solution. Filtration treatment allows for the production of high-quality recycled resin with minimal foreign matter contamination.

[0118] (Dihydroxy compound) The dihydroxy compound is not particularly limited, but from the viewpoint of improving the solubility of the resin (raw material), -CH ２ A dihydroxy compound with a -CH-OH terminus is preferred. The dihydroxy compound may be used alone or in combination of two or more.

[0119] In some embodiments, the dihydroxy compound includes a dihydroxy compound corresponding to a constituent unit of the thermoplastic resin contained in the raw material. That is, a constituent unit derived from the dihydroxy compound is included in the constituent unit of the thermoplastic resin. By adding the same dihydroxy compound as the monomer unit contained in the thermoplastic resin, a polymerization reaction (transesterification reaction) proceeds, enabling the resin to be made higher molecular weight and its molecular weight adjusted. It is preferable to add the dihydroxy compound in a composition similar to or the same as the constituent unit of the thermoplastic resin that constitutes the raw material. If the composition is similar to or the same as the constituent unit of the raw material resin, it is possible to produce a resin of the same material, which is preferable from a recycling perspective compared to producing a resin of a new material.

[0120] For example, if the thermoplastic resin in the raw material contains the above-mentioned constituent units (A), (B), or (D), which are dihydroxy-derived constituent units, a polycarbonate resin as a recycled resin can be produced by reacting them with dihydroxy compounds (diols) represented by formulas (1), (2), and / or (4) corresponding to these dihydroxy-derived constituent units and a diester carbonate. For example, if the thermoplastic resin in the raw material contains the above-mentioned constituent units (A), (B), or (D), which are dihydroxy-derived constituent units, and the above-mentioned constituent unit (C) or (E), which are dicarboxylic acid-derived constituent units, a polyester carbonate resin as a recycled resin can be produced by reacting them with dihydroxy compounds (diols) represented by formulas (1), (2), and / or (4) corresponding to these dihydroxy-derived constituent units, monomer compounds (dicarboxylic acid (ester) compounds) represented by formulas (3) and / or (5) corresponding to these dicarboxylic acid-derived constituent units and a diester carbonate. For example, if the thermoplastic resin in the raw material contains the above-mentioned constituent units (A), (B), (C), or (D), which are dihydroxy-derived constituent units, and the above-mentioned constituent unit (C) or (E), which are dicarboxylic acid-derived constituent units, then a polyester resin as a recycled resin can be produced by reacting a dihydroxy compound (diol) represented by formula (1), (2), (3), and / or formula (4) corresponding to these dihydroxy-derived constituent units with a monomer compound (dicarboxylic acid (ester) compound) represented by formula (3) and / or formula (5) corresponding to these dicarboxylic acid-derived constituent units. In the above case, compounds that derive constituent units of other polycarbonate resins, compounds that derive constituent units of other resins (polyester resin, polyester carbonate resin, polyolefin resin), etc., can be used in combination with compounds that derive constituent units of other polycarbonate resins, compounds that derive constituent units of other resins (polyester resin, polyester carbonate resin, polyolefin resin), etc.

[0121] In some embodiments, the thermoplastic resin contained in the raw material includes constituent unit (A) and constituent unit (B), and the dihydroxy compound includes at least one selected from the dihydroxy compound represented by the general formula (1) and the dihydroxy compound represented by the general formula (2). In some embodiments, it is preferable that the dihydroxy compound includes at least one dihydroxy compound which is a monomer represented by the general formula (1) or (2). In some embodiments, the dihydroxy compound includes at least one selected from BNE, BNEF, DP, BPEF and BPPEF(PG).

[0122] (Diester carbonates) Examples of diester carbonates include diphenyl carbonate (DPC), ditriyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate. Among these, diphenyl carbonate is particularly preferred.

[0123] The amount of diester carbonate added is not particularly limited, but since diester carbonate polymerizes with the dihydroxy compound to form a resin component, it is preferable that the molar ratio is adjusted. The amount of diester carbonate used is preferably 0.97 to 1.20 moles, more preferably 0.98 to 1.10 moles, and even more preferably 1.00 to 1.10 moles per mole of the dihydroxy compound.

[0124] (Catalyst) A catalyst may be added in step D. Including a catalyst can accelerate the polymerization reaction and increase the molecular weight of the recycled resin. Alkali metal catalysts are preferred from the standpoint of suppressing excessive depolymerization reactions and from the standpoint of cost-effectiveness and ease of availability.

[0125] Examples of alkali metal catalysts include organic salts, inorganic salts, oxides, hydroxides, hydrides, or alkoxides of alkali metals. Specifically, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium phenylborohydride, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium phenyl phosphate, disodium, dipotassium, dicesium, or dilithium salts of bisphenol A, and sodium, potassium, cesium, or lithium salts of phenol are used. Among the above alkali metal catalysts, strongly alkaline compounds tend to promote depolymerization reactions. From the viewpoint of suppressing the depolymerization reaction, the catalysts are preferably sodium bicarbonate, sodium carbonate, cesium carbonate, and potassium carbonate, and more preferably sodium bicarbonate, sodium carbonate, and cesium carbonate. One type of catalyst may be used, or multiple types may be used in combination. In order to suppress the decrease in the molecular weight of the resin, step D is preferably carried out in the absence of a strong alkali.

[0126] In addition to alkali metal catalysts, alkaline earth metal catalysts, nitrogen-containing compounds such as tetramethylammonium hydroxide, phosphorus-containing compounds, and transesterification catalysts such as titanium tetraisopropoxide and titanium tetrabutoxide may also be used as catalysts.

[0127] The amount of catalyst to add is 1 × 10⁻¹⁶ per 1 mole of the total dihydroxy compounds added. －９ ~1 x 10 －３ Mole ratio, 1 x 10 －７ ~1 x 10 －４ It is preferable to use it in molar ratio. By using such a range, the polymerization reaction of the dihydroxy compound can be promoted in step D.

[0128] In step D, it is not necessary to add a catalyst. In such cases, a resin with a low thermal history can be obtained.

[0129] The raw materials may contain catalysts used during resin production, and heating such raw materials may cause a depolymerization reaction even if no catalyst is added in step D. From the viewpoint of suppressing excessive depolymerization reactions, if the raw materials contain a catalyst, it is preferable that the catalyst is an alkali metal catalyst. Specific examples of alkali metal catalysts are the same as those exemplified as catalysts that may be added in the above steps.

[0130] The total content of the catalyst (preferably an alkali metal catalyst) in the raw materials is preferably in the range of 0.1 to 1000 ppm by weight, more preferably in the range of 0.1 to 100 ppm by weight, and even more preferably in the range of 0.1 to 10 ppm by weight, relative to the total weight (100% by weight) of the raw materials. The catalyst content in the raw materials can be measured by methods such as ICP emission spectrometry, X-ray fluorescence analysis, and atomic absorption spectrometry. An example of a specific measurement method using ICP mass spectrometry (ICP-MS) is as follows: After sulfuric acid carbonization of the sample, the metal concentration is measured by ICP-MS. That is, 2 g of the resin sample is weighed into a synthetic quartz beaker, 2.5 mL of sulfuric acid is added, and just before carbonization, 0.1 mL of sulfuric acid is added while heating on a hot plate. Subsequently, the beaker is covered with a quartz dish and heated in an electric furnace at 500°C for 10 hours to carbonize. Furthermore, thermal acid decomposition is performed by adding sulfuric acid and heating to dryness, and then adding nitric acid and heating to dryness. Add nitric acid solution to make a total volume of 50 mL, heat to 50°C, and perform quantitative analysis by ICP-MS. ICP-MS instrument: Shimadzu Corporation: ICPE-9000

[0131] The reaction solvent is not particularly limited as long as the polymerization reaction can proceed, but examples include aryl alcohols, aliphatic hydrocarbon solvents, and aromatic hydrocarbon solvents. Among these, aryl alcohols are preferred because of their excellent compatibility with the raw material resins. Furthermore, when diaryl carbonate is used in the reaction, aryl alcohol is produced as a by-product, so using aryl alcohol as the reaction solvent is also preferable because it prevents the introduction of extraneous (other new types of) impurities. The reaction solvent may be used alone or in combination of two or more. Preferably, the polymerization reaction is carried out in the form of a reaction solution in which the raw materials are dissolved in the reaction solvent.

[0132] (Preparation of reaction solution) Aryl alcohols are compounds in which the hydrogen atoms of an aryl group are replaced with hydroxyl groups. Aryl alcohols are not particularly limited as long as they have good compatibility with the starting materials and their boiling point is the same as or higher than the glass transition temperature of the resin components contained in the starting materials, for example, substituted or unsubstituted phenols. The substituents of the phenol can be selected from a wide range of organic groups, for example, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and halogen atoms. Among these, aryl alcohols are preferably selected from unsubstituted phenols or mono-, di- or tri-substituted phenols (for example, o-, m- or p-cresol, o-, m- or p-ethylphenol, o-, m- or p-chlorophenol, o-, m- or p-methoxyphenol, 2,3-, 2,4- or 3,4-dimethylphenol, etc.) because they are easy to handle, inexpensive, and high purity is available on the market, and unsubstituted phenols are more preferable. Unsubstituted phenols are often present in small amounts in waste resins, thus avoiding the introduction of new impurities and minimizing their impact on the resin's properties. Aryl alcohols may be used alone or in combination of two or more types. The amount of aryl alcohol added is not particularly limited, but the weight ratio of raw material to aryl alcohol (waste resin:aryl alcohol) is preferably in the range of 1:0.1 to 1:6, more preferably in the range of 1:0.5 to 1:5, and even more preferably in the range of 1:0.8 to 1:4. If the aryl alcohol content is too low, the solubility of the raw material in the aryl alcohol decreases. On the other hand, if the amount of aryl alcohol is too high, excessive depolymerization of the raw material is likely to occur, excessive energy is required to remove the aryl alcohol after the reaction, and there may be problems with efficiency and environmental impact. By keeping the amount within the above range, it is possible to improve the solubility of the raw material, suppress the decrease in molecular weight of the recycled resin, and / or improve energy efficiency.

[0133] The method for preparing the reaction solution is not particularly limited as long as it can dissolve the raw materials in the aryl alcohol, but a preferred method is to mix the aryl alcohol and the raw materials and heat them. The heating temperature is not particularly limited as long as it is the temperature at which the raw materials dissolve in the aryl alcohol, but a temperature of 140°C to 280°C is preferred. A temperature of 140°C or higher is often above the glass transition temperature (Tg) of the resin, resulting in excellent resin solubility. A temperature of 280°C or lower is preferred in that it can suppress reactions that produce coloring components, such as thermal transition reactions. The heating temperature is preferably 140 to 250°C, more preferably 140 to 230°C, and even more preferably 160 to 200°C. Within this temperature range, solubility is excellent, and the viscosity of the reaction solution decreases, reducing the stirring power. The pressure is not particularly limited, but from the viewpoint of preventing distillation or volatilization of the aryl alcohol from the system, 90 to 105 kPa is preferred, 95 to 105 kPa is more preferred, and 95 to 102 kPa is even more preferred.

[0134] (Filtration Step) After preparing the reaction solution, it is preferable to filter the reaction solution with a filter as needed. The intrinsic viscosity of the reaction solution subjected to filtration is preferably 0.070 dL / g or less, more preferably 0.065 dL / g or less, and even more preferably 0.060 dL / g or less, in terms of the performance and productivity of the filter used for filtration (smooth and rapid filtration). There is no particular lower limit to the intrinsic viscosity of the reaction solution, but it is preferably 0.005 dL / g or more, more preferably 0.010 dL / g or more, and even more preferably 0.015 dL / g or more, in order to ensure stable filtration.

[0135] From the viewpoint of productivity, the filtration pressure is preferably 40 kPa or higher, more preferably 80 kPa or higher, and even more preferably 130 kPa or higher. From the viewpoint of equipment protection, the filtration pressure is preferably 220 kPa or lower, more preferably 200 kPa or lower, and even more preferably 170 kPa or lower.

[0136] The pore size of the filter used for filtration is preferably 30 μm or less, more preferably 20 μm or less, and even more preferably 15 μm or less, in terms of removing foreign matter. Smaller pore sizes improve filtration accuracy, but they are more prone to clogging and reduce productivity. Therefore, the pore size of the filter is preferably 1 μm or more, more preferably 5 μm or more, and even more preferably 7 μm or more.

[0137] The filters used for filtration are not particularly limited as long as they possess the strength and heat resistance necessary for filtering the reaction solution. For example, filters made of metal, ceramic, stainless steel, resin, or combinations thereof can be used. Among these, stainless steel is preferred from the viewpoint of good heat resistance, corrosion resistance, and mechanical properties. Known filter shapes such as candle type, pleated type, and leaf disc type can be used, and it is preferable to use multiple filters in combination to obtain a large filtration area.

[0138] The filtration rate is preferably in the range of 30 kg / min to 600 kg / min, more preferably in the range of 50 kg / min to 500 kg / min, even more preferably in the range of 100 kg / min to 450 kg / min, and particularly preferably in the range of 200 kg / min to 450 kg / min, in terms of productivity (smooth and rapid filtration) and removal of foreign matter. It is preferable to adjust the pressure, filter pore size, and intrinsic viscosity of the reaction solution so that the filtration rate falls within this range.

[0139] The filtration time (the time it takes to transfer the reaction solution to the filter) is preferably 100 to 1400 seconds, more preferably 200 to 800 seconds, and even more preferably 300 to 500 seconds, in order to ensure an efficient production cycle.

[0140] The filtration temperature is not particularly limited, but it is preferable to filter at the same temperature as the reaction solution preparation step in order to reduce monomer modification and the thermal history applied to the resin, and to avoid delaying the batch cycle. In some embodiments, the filtration temperature is above the boiling point of the aryl alcohol and below 230°C (more preferably above the boiling point of the aryl alcohol and below 200°C). The filtration temperature refers to the temperature of the waste resin composition (filtrate) immediately after passing through the filter.

[0141] (Polymerization Reaction) The polymerization conditions are not particularly limited as long as they allow the polymerization reaction between the raw materials and, if necessary, the present dihydroxy compounds and / or diester carbonates to proceed. For example, when the above-mentioned aryl alcohol is used as the reaction solvent, the polymerization reaction proceeds by removing the aryl alcohol from the reaction system, and a regenerated resin is obtained. For example, the aryl alcohol can be removed by heating to a temperature of 180 to 260°C (preferably 190 to 260°C, more preferably 190 to 250°C) under a pressure of 0.01 to 105 kPa (preferably 0.1 to 105 kPa). Preferably, the aryl alcohol is removed by gradually heating the mixture to a maximum temperature of around 260°C (preferably 250°C) in accordance with the rate of aryl alcohol removal, while decreasing the pressure (for example, decreasing the pressure from the range of 90 to 105 kPa to a pressure of 0.01 to 5 kPa).

[0142] The recycled resin obtained after the polymerization reaction is a mixture of recycled resin components derived from molded waste and resin components made from added dihydroxy compounds and, if necessary, present diester carbonates, or a composition thereof. In other words, the recycled resin may be a resin in which structural units derived from diol compounds are incorporated into a recycled resin derived from waste resin, a blend of a recycled resin and a resin containing structural units derived from dihydroxy compounds, or a composition containing these.

[0143] Furthermore, if a diester carbonate is included, an aryl alcohol may be produced by polymerization (transesterification) between the dihydroxy compound and the diester carbonate. For example, if diphenyl carbonate (DPC) is used as the diester carbonate compound, phenol may be produced by polymerization with the dihydroxy compound. In these cases, in step D, in addition to the reaction solvent (e.g., aryl alcohol) in the reaction solution, the aryl alcohol produced by the reaction between the dihydroxy compound and the diester carbonate is also removed.

[0144] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these. Unless otherwise specified, "%" is based on weight. Unless otherwise specified, the examples were carried out at room temperature. "Room temperature" typically ranges from about 10°C to about 35°C, for example, 25°C.

[0145] (Evaluation of Resin) The resin was evaluated using the following methods: (1) The resin was molded to a thickness of 3 mm by haze injection molding, and the haze was measured using a spectroscopic haze meter. The haze values ​​were obtained in accordance with JIS K-7136:2000. Measuring instrument: SH 7000 manufactured by Nippon Denshoku Industries Co., Ltd. (2) Refractive index (nD) Based on JIS B 7071-2:2018, the resin was molded by injection molding to obtain a V-block, which was used as a test specimen. The refractive index was measured using a refractometer at 23°C and a wavelength of 589 nm. Refractometer: KPR-3000 manufactured by Shimadzu Corporation (3) Weight-average molecular weight Mw The weight-average molecular weight (Mw) was calculated using gel permeation chromatography (GPC), with tetrahydrofuran as the developing solvent, and a calibration curve was created using standard polystyrene with a known molecular weight (molecular weight distribution = 1). Based on this calibration curve, the weight-average molecular weight (Mw) was calculated from the retention time of the GPC.

[0146] 1. Thermoplastic resins PC-1, PC-2, and PC-3 were synthesized as synthetic resin samples of thermoplastic resins.

[0147] (Raw materials) BPEF: 9,9-bis[4-(2-hydroxyethoxy)-phenyl]fluorene BPPEF: 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene BNEF: 9,9-bis[6-(2-hydroxyethoxy)naphthalene-2-yl]fluorene BNE: 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene DPC: diphenyl carbonate

[0148] [Synthesis Example 1: Synthesis of Thermoplastic Resin PC-1 (BPEF-HOMO)] The raw materials are 20.86 kg (47.56 mol) of 9,9-bis[4-(2-hydroxyethoxy)-phenyl]fluorene (BPEF), 10.5 kg (49.02 mol) of diphenyl carbonate (DPC), and 2.5 × 10 －２ 16 ml of a mol / liter sodium bicarbonate aqueous solution (4.0 x 10⁻⁶) －４ For every mole, i.e., 1 mole of the total dihydroxy compound, 8.4 × 10 －６ The molal (mol) was placed in a 50 L reactor equipped with a stirrer and distillation apparatus, and heated to 180°C under a nitrogen atmosphere of 760 mmHg. Complete dissolution of the raw materials was confirmed 30 minutes after the start of heating, and stirring was then carried out under the same conditions for 120 minutes. Subsequently, the pressure was adjusted to 200 mmHg, and the temperature was increased to 200°C at a rate of 60°C / hr. At this time, the start of distillation of the by-product phenol was confirmed. The reaction was then carried out while maintaining the temperature at 200°C for 20 minutes. Furthermore, the temperature was increased to 230°C at a rate of 75°C / hr, and 10 minutes after the end of the heating, the pressure was reduced to 1 mmHg or less over 2 hours while maintaining the temperature at that temperature. Subsequently, the temperature was increased to 245°C at a rate of 60°C / hr, and stirring was carried out for a further 40 minutes. After the reaction was complete, nitrogen was introduced into the reactor to return it to atmospheric pressure, and the resulting resin was removed while pelletizing to obtain a thermoplastic polycarbonate resin (PC1:BPEF homopolymer resin, Mw = 28,000).

[0149] [Synthesis Example 2: Synthesis of Thermoplastic Resin PC-2 (BNE / BPEPEF)] BNE / BPEF = x / y = 18.4 / 22.5 (mol%). The raw materials were 6.9 kg (18.4 mol) of 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 13.3 kg (22.5 mol) of 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (BPEF), 9.0 kg (42.2 mol) of diphenyl carbonate (DPC), and 2.5 × 10 －２ Moles / liter of sodium bicarbonate (NaHCO3) ３ ) 16 ml aqueous solution (4.0 x 10 －４ For every mole, i.e., 1 mole of the total dihydroxy compound, 8.4 × 10 －６A thermoplastic polycarbonate resin (PC-2: BNE / BPEPEF, Mw = 44,000) was obtained in the same manner as the synthesis of PC1, except that moles were used.

[0150] [Synthesis Example 3: Synthesis of Thermoplastic Resin PC-3 (BNEF / BNE / BPEPEF)] BNEF / BNE / BPPEF = x / y / z = 12.1 / 20.03 / 14.8 (mol%). The raw materials are 4.53 kg (12.1 mol) of 9,9-bis[6-(2-hydroxyethoxy)naphthalene-2-yl]fluorene (BNEF), 7.5 kg (20.03 mol) of 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 8.72 kg (14.8 mol) of 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (BPPEF), 10.25 kg (47.87 mol) of diphenyl carbonate (DPC), and 2.5 × 10 －２ Moles / liter of sodium bicarbonate (NaHCO3) ３ ) 16 ml aqueous solution (4.0 x 10 －４ For every mole, i.e., 1 mole of the total dihydroxy compound, 8.4 × 10 －６ The molal (molar) was placed in a 50 L reactor equipped with a stirrer and distillation apparatus, and heated from 25°C to 180°C over 30 minutes under a nitrogen atmosphere of 760 mmHg. Complete dissolution of the raw materials was confirmed 30 minutes after the start of heating. The mixture was then stirred at 180°C for 120 minutes. Subsequently, the pressure was adjusted to 200 mmHg, and the temperature was increased to 200°C at a rate of 60°C / hr. At this time, the start of distillation of the by-product phenol was confirmed. The reaction was then maintained at 200°C for 20 minutes. Furthermore, the temperature was increased to 230°C at a rate of 75°C / hr, and 10 minutes after the end of the heating, the pressure was reduced to 1 mmHg or less over 2 hours while maintaining the temperature at that temperature. Subsequently, the temperature was increased to 245°C at a rate of 60°C / hr, and the mixture was stirred for a further 40 minutes. After the reaction was complete, nitrogen was introduced into the reactor to return it to atmospheric pressure, and the resulting thermoplastic resin was pelletized and removed to obtain polycarbonate resin (PC-3, BNEF / BNE / BPEPEF, Mw = 31,000), which is a thermoplastic resin.

[0151] (Pelletization) The resins obtained above (PC-1, PC-2, PC-3) were melt-kneaded with 15 ppm by weight of tetrabutylphosphonium dodecylbenzenesulfonate (MGA-614, manufactured by Takemoto Oil Co., Ltd.) as a deactivator, 300 ppm by weight of 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane (PEP-36, manufactured by ADEKA Corporation) as a release agent, and 1000 ppm by weight of pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (AO-60, manufactured by ADEKA Corporation) as an antioxidant, and then pelletized.

[0152] 2. Preparation of Calibration Curve <Method for Mixing Resin Composition for Calibration Curve Preparation> The composition was mixed by melt extrusion using a twin-screw extruder. [Extrusion Conditions] Equipment: Extruder (TEX28V, manufactured by Japan Steel Works Ltd.) Screw temperature: 280℃ Rotation speed: 300rpm Feed: 15 kg / h Purge amount: 1.2 kg (Sampling was taken after purging 1.2 kg)

[0153] <Forming of Raman Spectroscopy Test Specimens (3mm Thick Plate)> The specimens were formed by injection molding under the following molding conditions (A or B). (1) Molding Method A [Molding Conditions] Equipment: ROBOSHOT S2000i30B manufactured by FANAC Equipment conditions: Cylinder temperature 250℃, injection speed 70mm / s, screw rotation speed 50rpm, back pressure 1Mpa

[0154] (2) Molding Method B [Molding Conditions] Equipment: Injection molding machine J55AD manufactured by Japan Steel Works Ltd. Equipment conditions: Cylinder temperature 250℃, injection speed 70mm / s, screw rotation speed 100rpm, back pressure 1MPa

[0155] <Measurement of Raman Spectroscopic Spectroscopy> The measurement was performed using a Raman spectrometer. The measurement and analysis conditions are as follows. (1) Raman spectroscopy method A [Measurement conditions] Equipment used: Palmtop Raman PR-1w (manufactured by JASCO Corporation) Excitation wavelength: 785.00 nm Laser intensity: Low Exposure time: 5 sec Number of integrations: 8 Background correction: JascoBackGroundData.BKG Ambient temperature: Room temperature (25℃) Focus setting: Focus was set so that the Raman peak intensity of the standard polystyrene sample was maximized [Analysis conditions] (Fluorescence correction) Shape: Circle Judgment interval: 1 Smoothing on baseline: OFF R: 101 A: 1 Smoothing on judgment spectrum: OFF Convolution width: 5-25 (Peak normalization) Normalization position: 1606 Base correction: No base Base position: 1600 (2) Raman spectroscopy method B The measurement was performed in the same manner as measurement method A above, except that the exposure time was changed to 7 sec and the number of integrations to 4.

[0156] [Calibration Curve Creation Example 1] Molding Method A / Raman Spectroscopy Method A PC-2 and PC-3 were kneaded together using the above kneading method in weight ratios of 100 / 0, 95 / 5, 90 / 10, 80 / 20, 70 / 30, 50 / 50, 70 / 30, 80 / 20, 90 / 10, and 95 / 5, totaling 2.0 kg, to obtain a resin composition for calibration curve creation with a known resin ratio (resin content). A 3 mm thick plate of this resin composition was obtained using the above molding method A, and the Raman scattering spectrum was measured according to the above Raman spectroscopy measurement method A. Figure 1 shows the Raman scattering spectrum.

[0157] (1) 1410 cm -1 1410cm -1 The peak was observed when PC-3 was present in high concentrations, but not when PC-2 was present in high concentrations. Therefore, 1410 cm -1 The peak was selected as the Raman scattering peak attributed to PC-3, and measured at 1410 cm⁻¹. －１Based on the peak intensity, a calibration curve for PC-3 was created. Table 1 and Figure 2 show the PC-3 content and 1410 cm⁻¹. -1 This shows the relationship with the intensity of the Raman scattering peak.

[0158] (2) 1375 cm -1 1375cm -1 The peak is observed with high intensity when PC-3 is present in high content, but the intensity is weak when PC-2 is present in high content. Therefore, 1375 cm -1 The peak at 1375cm was selected as the Raman scattering peak attributed to PC-3. -1 Based on the peak intensity, a calibration curve for PC-3 was created. Table 2 and Figure 3 show the PC-3 content and 1375 cm⁻¹. -1 This shows the relationship with the intensity of the Raman scattering peak.

[0159] (3) 1025 cm -1 1025cm -1 The peak is observed in both PC-2 and PC-3, but the intensity in PC-3 is stronger than that in PC-2. Therefore, 1025cm -1 The peak was selected as the peak originating from PC-3, and the value is 1025cm. -1 A calibration curve was created based on the peak intensity. Table 3 and Figure 4 show the PC-3 content and 1025cm -1 This shows the relationship with the intensity of the Raman scattering peak.

[0160] [Calibration Curve Creation Example 2] Molding Method A / Raman Spectroscopy Method B Except for obtaining a molded body by molding method A with PC-2 and PC-3 in weight ratios of 98 / 2, 99 / 1, 99.5 / 0.5, 99.8 / 0.2, and 99.9 / 0.1 respectively, and following the above-mentioned Raman spectroscopy method B, the Raman scattering spectrum was measured in the same manner as in "Calibration Curve Creation Example 1".

[0161] (1) 1375 cm -1 1375cm -1 The peak is observed when PC-3 is present in high concentrations, but its intensity is weak when PC-2 is present in high concentrations. Therefore, 1375 cm-1 The peak was selected as the Raman scattering peak originating from PC-3, at 1375 cm⁻¹. -1 Based on the peak intensity, a calibration curve for PC-3 was created. Table 4 and Figure 5 show the PC-3 content and 1375 cm⁻¹. -1 This shows the relationship with the intensity of the Raman scattering peak.

[0162] [Calibration Curve Creation Example 3] Molding Method A / Raman Spectroscopy Method B PC-2 and PC-1 were kneaded together using the above kneading method in weight ratios of 98 / 2, 99 / 1, 99.5 / 0.5, 99.8 / 0.2, and 99.9 / 0.1 respectively to a total weight of 2.0 kg, thereby obtaining a resin composition for calibration curve creation with a known resin ratio (resin content). A 3 mm thick plate of this resin composition was obtained using the above molding method A, and the Raman scattering spectrum was measured according to the above Raman spectroscopy method B.

[0163] (1) 1146 cm -1 1146cm -1 The peak was observed when PC-1 was present in high concentrations, but not when PC-2 was present in high concentrations. Therefore, 1146 cm -1 The peak at 1146cm was selected as the Raman scattering peak attributed to PC-1. -1 Based on the peak intensity, a calibration curve for PC-1 was created. Table 5 and Figure 6 show the content ratio of PC-3 and 1146 cm. -1 This shows the relationship with the intensity of the Raman scattering peak.

[0164] [Calibration Curve Creation Example 2'] Molding Method B / Raman Spectroscopy Method B The Raman scattering spectrum was measured in the same manner as in "Calibration Curve Creation Example 2," except that the molding of the test specimen followed the molding method B described above.

[0165] (1) 1375 cm -1 1375cm -1 The peak is observed when PC-3 is present in high concentrations, but its intensity is weak when PC-2 is present in high concentrations. Therefore, 1375 cm -1 The peak was selected as the Raman scattering peak originating from PC-3, at 1375 cm⁻¹. -1Based on the peak intensity, a calibration curve for PC-3 was created. Table 6 and Figure 7 show the PC-3 content and 1375 cm⁻¹. -1 This shows the relationship with the intensity of the Raman scattering peak.

[0166] [Calibration Curve Creation Example 3'] Molding Method B / Raman Spectroscopy Method B The Raman scattering spectrum was measured in the same manner as in "Calibration Curve Creation Example 3," except that the molding of the test specimen followed the molding method B described above.

[0167] (1) 1146 cm -1 1146cm -1 The peak was observed when PC-1 was present in high concentrations, but not when PC-2 was present in high concentrations. Therefore, 1146 cm -1 The peak at 1146cm was selected as the Raman scattering peak attributed to PC-1. -1 Based on the peak intensity, a calibration curve for PC-1 was created. Table 7 and Figure 8 show the PC-1 content and 1146 cm³. -1 This shows the relationship with the intensity of the Raman scattering peak.

[0168] In all of Figures 2 to 8, a linear correlation was observed between the Raman scattering peak intensity attributed to the analyte resin (PC-1 or PC-3) in the molded body and the resin content in the molded body, confirming good linearity of the calibration curve over a wide range of content. By using the above calibration curve, the analyte resin can be quantified from the Raman scattering peak intensity of a measurement sample in which the concentration of the analyte resin is unknown.

[0169] 3. Quantitative Determination of Thermoplastic Resin [Example 1] PC-2 was molded as an optical lens, and the molded waste (runners, sprues, etc.) discharged from the molding process was collected. Since the molding machine molds resins including PC-1 and PC-3, the collected molded waste mainly contains PC-2, but there is a high possibility that resins other than PC-2, such as PC-1 and PC-3, are also mixed in. The molded waste was crushed using a crusher (crusher manufactured by Tanaka Co., Ltd.) to an average particle size of about 3.3 mm (about 2.5 to 4.0 mm), and then mixed to obtain a uniformly blended pulverized material. The pulverized material was molded according to molding method B described in "2. Preparation of Calibration Curve" above to obtain a molded body of molded waste. The Raman scattering spectrum was measured according to Raman spectroscopy measurement method B, and PC-3 and PC-1 in the molded body were quantified using the calibration curves created in "Calibration Curve Preparation Example 2'" and "Calibration Curve Preparation Example 3'" using the same molding method B as the molded body of molded waste.

[0170] (Quantitative measurement of PC-3) 1375cm -1 The Raman scattering peak intensity was 72.2720. From the calibration curve created in "Calibration Curve Creation Example 2'" above, the PC-3 content in the recovered molded waste was determined to be 0%. y = 2.0161 × 72.2720 - 161.43 y = 0 or less

[0171] (Quantitative measurement of PC-1) 1146cm -1 The peak intensity was 25.3517. From the calibration curve created in "Calibration Curve Creation Example 3'" above, the PC-1 content in the recovered molded waste was calculated to be 2.202%. y = 3.5942 × 25.3517 - 88.917 y = 2.202

[0172] [Comparative Example 1] 50g of the crushed material from Example 1 was laid flat and irradiated with 254nm ultraviolet light (UV-C) (device name: AS ONE handy UV lamp). Materials that emitted light (PC-2, PC-3) and those that did not (PC-1) were separated by visual inspection, and the materials to be removed (non-luminescent resin) were picked up and their weight measured. The contamination ratio was calculated from the following formula (1): Contamination ratio (%) = Weight of the picked-up materials to be removed / 50 × 100 Formula (1) As a result, the waste molded product contained 2.8360% by weight of resin that did not emit light under UV light, such as PC-1.

[0173] [Example 2] Molding waste from a different lot than that used in Example 1 was analyzed in the same manner as in Example 1.

[0174] (Quantitative measurement of PC-3) 1375cm -1 The peak intensity was 80.776. From the calibration curve created in "Calibration Curve Creation Example 2'" above, the PC-3 content in the recovered molded waste was calculated to be 1.4224% by weight. y = 2.0161 × 80.776 - 161.43 y = 1.4224

[0175] (Quantitative analysis of PC-1) 1146 cm -1 The peak intensity was 24.8722. From the calibration curve created in "Calibration Curve Creation Example 3'" above, the PC-1 content in the recovered molded waste was calculated to be 0.4787%. y = 3.5942 × 24.8722 - 88.917 y = 0.4787

[0176] [Comparative Example 2] Separation by UV light was performed in the same manner as in Comparative Example 1, except that the molded waste used in Example 2 was used. The molded waste contained 0.1714% by weight of resin that did not emit light under UV light, like PC-1.

[0177] [Example 3] Molding waste from a different lot than that used in Example 1 was analyzed in the same manner as in Example 1. (Quantitative determination of PC-3) 1375 cm -1The peak intensity was 81.0118. From the calibration curve created in "Calibration Curve Creation Example 2'" above, the PC-3 content in the recovered molded waste was calculated to be 1.8980% by weight. y = 2.0161 × 81.0118 - 161.43 y = 1.898 (Quantification of PC-1) 1146cm -1 The peak intensity was 24.8026. From the calibration curve created in "Calibration Curve Creation Example 3'" above, the PC-1 content in the recovered molded waste was calculated to be 0.2285%. y = 3.5942 × 24.8026 - 88.917 y = 0.2285

[0178] [Comparative Example 3] Separation by UV light was performed in the same manner as in Comparative Example 1, except that the molded waste used in Example 2 was used. The waste molded product contained 0.0990% by weight of resin that did not emit light under UV light, like PC-1.

[0179] 4. Production of Recycled Resin (Polymerization) [Example a] 333 kg of resin (pulverized molded waste) quantified in Example 1, dihydroxy compounds (BPEF_417 kg, BNE_216 kg), 283 kg of DPC, 667 kg of phenol, and 33 ml of 0.47 M NaHCO3aq as a catalyst were placed in a reaction solution preparation vessel and left to stand at 103 kPaA and 150°C for 45 minutes. After 45 minutes, stirring was started and the temperature was raised to 190°C over 22 minutes. Thereafter, stirring was continued for 130 minutes at 103 kPaA (pressure gradually increased with heating) and 190°C, and dissolution was confirmed visually to obtain the reaction solution. The bottom valve of the reaction solution preparation vessel was opened and the mixture was filtered at a pressure of 150 kPaG using a 10 μm pore size filter (number of filters: 5, filtration area: 0.19 m² per filter). 2The reaction liquid was passed through SUS-316L (manufactured by Nippon Seisen Co., Ltd.) and delivered to the reaction vessel. After the start of delivery, pressurization was stopped when the liquid level dropped to a predetermined amount, and the bottom valve was closed when the pressure dropped and the reaction liquid was gone. The time from opening to closing the bottom valve was defined as the filter delivery time. The delivery time was 6 minutes. After the reaction liquid was delivered to the reactor, the pressure inside the reactor was reduced from 103 kPaA to 60 kPaA over 35 minutes at 210°C. The pressure was maintained for another 95 minutes, and then reduced from 60 kPaA to 32 kPaA over 60 minutes. The pressure was then maintained for another 40 minutes, and then reduced from 32 kPaA to 0 kPaA over 155 minutes. During this time, the reactor temperature was gradually increased from 210°C to 250°C. After the reaction was complete, the polycarbonate resin was pelletized and extracted to obtain polycarbonate resin similar to that of PC-2 described above. PC-2 obtained in Synthesis Example 2: Refractive index = 1.6600, Haze = 0.1% Resin obtained in Example a: Refractive index = 1.6600, Haze = 0.2%

[0180] [Example b] Polycarbonate resin was obtained in the same manner as in Example a, except that the reaction solution was sent directly to the reactor without being filtered for polymerization. Resin obtained in Example b: refractive index = 1.6600, haze = 0.4%

[0181] [Example c] Polycarbonate resin was obtained in the same manner as in Example a, except that 333 kg of the resin (pulverized molded waste) quantified in Example 1, diols (BPEPEF_417 kg, BNE_216 kg), DPC_283 kg, phenol 667 kg, and 33 ml of 0.47 M NaHCO3aq as a catalyst were directly placed in the reactor and polymerized without dissolving the resin or filtering it. Resin obtained in Example c: refractive index = 1.6600, haze = 0.7%

[0182] The results are summarized in Table 8. As shown in Table 8, the quantitative analysis results of PC-1 contained in the molded waste in Examples 1 to 3 using Raman scattering spectra were similar to those of Comparative Examples 1 to 3 using UV. This result indicates that quantitative analysis using Raman scattering spectra is possible. In Examples 1 to 3, quantitative analysis using Raman scattering spectra made it possible to quantitatively analyze resins that do not emit UV light, such as PC-3, which are difficult to analyze using UV. Furthermore, in Examples a, b, and c, based on the quantitative analysis results, it was confirmed that by adding BPPEF and BNE as additional diol hydroxy compounds and diester carbonate (DPC) in predetermined amounts and polymerizing them, a recycled resin having a refractive index equivalent to that of resin PC-2 obtained in Synthesis Example 2 could be obtained. In particular, it was confirmed that by adding aryl alcohol (reaction solution preparation) and / or filtering the reaction solution during polymerization, the haze of the recycled resin was reduced, and a recycled resin with excellent transparency was obtained. The above results demonstrate that by using Raman scattering spectra, the type of thermoplastic resin in molded waste can be identified and quantitatively analyzed. Furthermore, these quantitative analysis results can be used to obtain recycled resin with superior performance (for example, optical properties such as refractive index and transparency, and properties similar to the original resin).

[0183]

Claims

1. A method for quantifying thermoplastic resin A contained in a molded article, comprising: step C1 measuring the intensity of a Raman scattering peak A attributed to the thermoplastic resin A from the Raman scattering spectrum of the molded article; and step C2 calculating the content ratio of the thermoplastic resin A contained in the molded article from the intensity of the Raman scattering peak A measured in step C1, with reference to a calibration curve showing the correlation between the content ratio of the thermoplastic resin A and the intensity of the Raman scattering peak A.

2. The method according to claim 1, wherein the calibration curve is prepared by measuring the intensity of the Raman scattering peak A of a plurality of calibration curve molded bodies obtained by molding resin compositions containing thermoplastic resin A at different known concentrations.

3. The method according to claim 1 or 2, wherein the Raman scattering peak A is measured with higher intensity for thermoplastic resin A than for other thermoplastic resins A.

4. The method according to claim 3, comprising selecting a Raman scattering peak A based on the Raman scattering spectrum of a molded article containing the thermoplastic resin A during or before step C1.

5. The method according to any one of claims 1 to 4, wherein the thermoplastic resin A is at least one selected from polycarbonate resin, polyester resin, and polyester carbonate resin.

6. The method according to any one of claims 1 to 5, wherein the proportion of thermoplastic resin in the molded article is 70% by weight or more of the total weight of the molded article.

7. The method according to any one of claims 1 to 6, wherein the thermoplastic resin A comprises at least one constituent unit selected from a monomer-derived constituent unit (A) represented by the following general formula (1), a monomer-derived constituent unit (B) represented by the following general formula (2), a monomer-derived constituent unit (C) represented by the following general formula (3), a monomer-derived constituent unit (D) represented by the following general formula (4), and a monomer-derived constituent unit (E) represented by the following general formula (5). [In formula (1), 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 alkoxyl group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxyl 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 represents 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 represents a fluorene group that is single-bonded or may have substituents; A and B each independently represent an alkylene group having 1 to 5 carbon atoms that may have substituents; m and n each independently represent an integer from 0 to 6; and a and b each independently represent an integer from 0 to 10. [In formula (2), R ｃ and R ｄ is 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 a substituent, an alkoxyl group having 1 to 20 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent, a cycloalkoxyl group having 5 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent, and Y is a single bond, a fluorene group which may have a substituent, -CR ２１ R ２２ -, -S-, -S(=O)-, -(CH ２ ) ｒ -, -O-, -(CH ２ ) ｒ -(SiR ２３ R ２４ -O) ｓ -SiR ２３ R ２４ -(CH ２ ) ｒ -, and -CR ２５ R ２６ -Ph-CR ２５ R ２６ - and is selected from the group consisting of, R ２１ , R ２２ , R ２３ , R ２４ , R ２５ and R ２６ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, or R ２１ and R ２２ , or R ２３ and R ２４ represent a carbocyclic or heterocyclic ring having 1 to 20 carbon atoms which may have a substituent formed by bonding to each other, Ph represents a phenyl group, r and s each independently represent an integer of 0 to 5000, A and B each independently represent an alkylene group having 1 to 5 carbon atoms which may have a substituent, p and q each independently represent an integer of 0 to 4, and a and b each independently represent an integer of 0 to 10. ] [In formula (3), 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 alkoxyl group, an optionally substituted C5-C20 cycloalkyl group, an optionally substituted C5-C20 cycloalkoxyl 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 a fluorene group that may have substituents; A and B each independently represent an alkylene group having 1 to 5 carbon atoms that may have substituents; m and n each independently represent an integer from 0 to 6; a and b each independently represent an integer from 0 to 10; R' and R'' each independently are selected from the group consisting of a hydroxyl group, a halogen atom, an alkoxy group having 1 to 20 carbon atoms that may have substituents, and an aryloxy group having 6 to 20 carbon atoms that may have substituents. [In formula (4), R ｇ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. [In formula (5), G １ and G ２ 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.

8. The method according to claim 7, wherein the thermoplastic resin A is selected from the group consisting of a resin comprising the constituent unit (A) and the constituent unit (B), a resin comprising the constituent unit (B) and the constituent unit (C), a resin comprising the constituent unit (B) and the constituent unit (D), a resin comprising the constituent unit (A), a resin comprising the constituent unit (B), a resin comprising the constituent unit (C), and a resin comprising the constituent unit (D).

9. The method according to claim 7, wherein the thermoplastic resin A is represented by any of the following formulas (I-1) to (I-14). (I-1) A resin containing a constituent unit represented by formula (i) (I-2) A resin containing a constituent unit represented by formula (iii) and a constituent unit represented by formula (v) (I-3) A resin containing a constituent unit represented by formula (ii), a constituent unit represented by formula (iii), and a constituent unit represented by formula (v) (I-4) A resin containing a constituent unit represented by formula (i) and a constituent unit represented by formula (iii) (I-5) A resin containing a constituent unit represented by formula (i) and a constituent unit represented by formula (vi) (I-6) A resin containing a constituent unit represented by formula (v), a constituent unit represented by formula (ii), and a constituent unit represented by formula (iii) (I-7) A resin containing a constituent unit represented by formula (ii), a constituent unit represented by formula (iii), and a constituent unit represented by formula (iv) (I-8) A resin containing a constituent unit represented by formula (v) (I-9) A resin containing a constituent unit represented by formula (i) and a constituent unit represented by formula (vii) (I-10) A resin containing a constituent unit represented by formula (ii) and a constituent unit represented by formula (vii). (I-11) A resin containing a constituent unit represented by formula (viiii), a constituent unit represented by formula (ix), a constituent unit represented by formula (x), and a constituent unit represented by formula (xi). (I-12) A resin containing a constituent unit represented by the following formula (viiii), a constituent unit represented by formula (ix), a constituent unit represented by formula (x), and a constituent unit represented by formula (xiiii). (I-13) A resin containing a constituent unit represented by the following formula (viiii), a constituent unit represented by formula (x), and a constituent unit represented by formula (xi). (I-14) A resin containing a constituent unit represented by formula (ii), a constituent unit represented by formula (iii), and a constituent unit represented by formula (xiv).

10. A method for determining the amount of thermoplastic resin A contained in molded waste, comprising: step A, pulverizing molded waste made of thermoplastic resin to obtain pulverized material (a); step B, molding the pulverized material (a) to obtain a molded body; and step C, determining the amount of thermoplastic resin A contained in the molded body, wherein step C is performed by the method described in any one of claims 1 to 9.

11. A method for producing recycled resin, comprising: step A, pulverizing a molded waste product made of thermoplastic resin to obtain pulverized material (a); step B, molding the pulverized material (a) to obtain a molded body; step C, quantifying the amount of thermoplastic resin A contained in the molded body; and step D, obtaining recycled resin from raw materials containing at least one of the pulverized material (a) and pulverized material (b) obtained by pulverizing the molded body, wherein step C is performed by the method described in any one of claims 1 to 9.

12. The method according to claim 10 or 11, wherein the molding waste comprises a sprue portion and / or a runner portion that is discharged after molding an optical material.

13. The method according to claim 10 or 11, wherein in step D, the raw material is further polymerized by adding a diester carbonate and / or a dihydroxy compound.

14. The method according to claim 10 or 11, wherein in step D, a diester carbonate and / or a dihydroxy compound and an aryl alcohol are further added to the raw materials to prepare a reaction solution, and polymerization is carried out.

15. The method according to claim 10 or 11, wherein in step D, a diester carbonate and / or a dihydroxy compound and an aryl alcohol are further added to the raw materials to prepare a reaction solution, which is then filtered and polymerized.

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