Recycled resin production method

Abstract

Provided is a recycled resin production method which provides excellent efficiency in recycling molding waste. The recycled resin production method includes: a step in which molding waste made of thermoplastic resins is irradiated with laser light, the types of thermoplastic resins in the molded product are identified on the basis of Raman scattered light scattered from the molding waste, and said resins are separated and recovered; and a step in which recycled resins are obtained from the separated and recovered resins. The thermoplastic resin includes at least one monomer type selected from a constituent unit (A) derived from a monomer represented by general formula (1), a constituent unit (B) derived from a monomer represented by general formula (2), a constituent unit (C) derived from a monomer represented by general formula (3), a constituent unit (D) derived from a monomer represented by general formula (4), and a constituent unit (E) derived from a monomer represented by general formula (5).　

Description

Recycled resin manufacturing method

[0001] The present invention relates to a method for producing recycled resin.

[0002] In recent years, concerns have grown over the deterioration of the natural environment and the increase in waste emissions, and efforts to recycle plastic products have become increasingly popular in an effort to realize a recycling-oriented society.

[0003] Injection molding is a typical method for producing plastic products. Specifically, a heated and molten resin is poured into a mold and cooled to produce a plastic product (molded body) molded into a predetermined shape. Depending on the injection molding method, molding waste resulting from the passage of the molten resin through the mold may also be produced along with the plastic product. For example, when producing a molded body, molding waste such as excess parts called "slips" that occur on the sprue, runners, and both ends of a film or sheet, and non-standard products, is generated. Such molding waste can be very large in volume during industrial production of plastic products, and recycling of molding waste has been considered.

[0004] For example, Patent Document 1 describes an invention relating to a manufacturing method for recycled thermoplastic resin molded products, in which sprue runners (molding waste) and / or defective molded products generated during the molding process of thermoplastic resin molded products are crushed and mixed with a new thermoplastic resin, and then a thermoplastic resin molded product is injection-molded again using the resulting mixture. This invention is characterized by the fact that molding is performed using a gas-assisted molding method under the same molding conditions as those used for molding with a new thermoplastic resin, even under conditions in which the melt flow characteristics of the mixture change. Patent Document 1 also describes the ability to obtain recycled resin molded products with stable dimensions and high commercial value, free of defects such as sink marks, distortion, and warpage.

[0005] Japanese Patent Application Laid-Open No. 2006-256339

[0006] When recycling waste thermoplastic resin moldings, the resulting waste moldings are collected and recycled into a waste composition. While it is desirable to collect the waste moldings by type of resin, the waste composition may contain a mixture of multiple types of resins. As a result, if the waste composition is recycled as is, the recycling efficiency and the quality of the recycled resin may be reduced.

[0007] Therefore, the present invention provides a means for improving the recycling efficiency and / or the quality of the obtained recycled resin in a method for producing recycled resin from molding waste.

[0008] The present invention is, for example, as follows.

[0009] [1] A method for producing recycled resin, comprising: a step of irradiating a molding waste product made of a thermoplastic resin with a laser beam, identifying the type of thermoplastic resin in the molding waste product based on Raman scattered light scattered from the molding waste product, and separately recovering the thermoplastic resin; and a step of obtaining recycled resin from the molding waste product that has been separately recovered, wherein the thermoplastic resin comprises at least one selected from a structural unit (A) derived from a monomer represented by the following general formula (1), a structural unit (B) derived from a monomer represented by the following general formula (2), a structural unit (C) derived from a monomer represented by the following general formula (3), a structural unit (D) derived from a monomer represented by the following general formula (4), and a structural unit (E) derived from a monomer represented by the following general formula (5). [In formula (1), R ａ and R ｂ each independently represents 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ R is selected from the group consisting of ｈrepresents 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 contains one or more hetero ring atoms selected from O, N, and S and which may have a substituent; X represents a single bond or an optionally substituted fluorene group; A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms; 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, 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 - 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 ６１ and R ６２ , or R ７１ and R ７２are bonded to each other to form a carbocyclic or heterocyclic ring having 1 to 20 carbon atoms, which may have a substituent; Ph represents a phenyl group; r and s each independently represent an integer of 0 to 5,000; 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 independently represents 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ R is selected from the group consisting of 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 contains one or more hetero ring atoms selected from O, N, and S and which may have a substituent; X represents a single bond or 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; a and b each independently represent an integer of 0 to 10; R' and R'' each independently are selected from the group consisting of a hydroxy group, a halogen atom, an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and an aryloxy group having 6 to 20 carbon atoms which may have a substituent. [In formula (4), R ｇ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. [In formula (5), G １ and G ２ each independently represents an alkylene group having 1 to 8 carbon atoms which may have a substituent,１ and K. ２ each independently represents a hydroxy group, an alkoxy group, or a halogen atom; R ｐ１ and R ｐ２ each independently represents a halogen atom, a cyano group, or an alkyl group having 1 to 8 carbon atoms which may have a substituent, １ and Ar ２ each independently represents a phenyl group or a naphthyl group which may have a substituent; １ and r ２ each independently represents an integer of 0 to 2; ３ and r ４ each independently represents an integer of 0 to 1.

[0010] [2] The manufacturing method according to [1], wherein the thermoplastic resin comprises at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by general formula (1), a structural unit (B) derived from a monomer represented by general formula (2), a structural unit (C) derived from a monomer represented by general formula (3), and a structural unit (D) derived from a monomer represented by general formula (4). [3] The manufacturing method according to [2], wherein the thermoplastic resin is selected from the group consisting of a resin consisting of the structural unit (A) and the structural unit (B), a resin consisting of the structural unit (B) and the structural unit (C), a resin consisting of the structural unit (B) and the structural unit (D), a resin consisting of the structural unit (A), a resin consisting of the structural unit (B), a resin consisting of the structural unit (C), and a resin consisting of the structural unit (D). [4] The manufacturing method according to [2], wherein the thermoplastic resin is represented by any of the following formulas (I-1), (I-2), (I-3), (II-1), (II-2), (II-3), (II-4), (II-5), or (II-6): [In the formula, x, y, and z represent the number of repeating units.] [5] The thermoplastic resin is selected from the group consisting of: (III-1) a resin containing a structural unit represented by the following formula (iii-a1), a structural unit represented by the formula (iii-a2), a structural unit represented by the formula (iii-a3), and a structural unit represented by the formula (iii-a4); (III-2) a resin containing a structural unit represented by the following formula (iii-a1), a structural unit represented by the formula (iii-a2), a structural unit represented by the formula (iii-a4), and a structural unit represented by the formula (iii-a5); (III-3) a resin containing a structural unit represented by the following formula (iii-a1), a structural unit represented by the formula (iii-a4), and a structural unit represented by the formula (iii-a6); The production method according to [1]. [6] The manufacturing method according to any one of [1] to [5], wherein the molding waste comprises a sprue portion and / or a runner portion that is discharged after molding the optical material.

[0011] [7] The manufacturing method according to any one of [1] to [6], wherein the sorting and recovery step is carried out continuously on a conveyor, and the molding waste products are supplied to the conveyor at a speed of 0.5 to 5 pieces / second. [8] The manufacturing method according to any one of [1] to [7], wherein the sorting and recovery step includes: collecting molding waste products to be recovered by spraying compressed air, and / or removing molding waste products not to be recovered by spraying compressed air. [9] The manufacturing method according to any one of [1] to [8], wherein the sorting and recovery step includes: supplying a waste composition containing the molding waste products to a vibrating transport bed and vibratingly transporting the waste composition, prior to the sorting and recovery step.

[10] The manufacturing method according to [9], wherein the sorting and recovery step includes: supplying molding waste products onto a conveyor at equal intervals.

[11] The manufacturing method according to

[10] , wherein the molding waste has an axial sprue portion and two or more runner portions extending evenly circumferentially from below the axis, and the molding waste is arranged in an aligned direction so that the tips of the axial sprues face upward.

[12] A method for separating and recovering molding waste, comprising the steps of irradiating a laser beam onto molding waste made of a thermoplastic resin, identifying the type of thermoplastic resin of the molding waste based on Raman scattered light scattered from the molding waste, and recovering the thermoplastic resin, wherein the thermoplastic resin comprises at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by the following general formula (1), a structural unit (B) derived from a monomer represented by the following general formula (2), a structural unit (C) derived from a monomer represented by the following general formula (3), a structural unit (D) derived from a monomer represented by the following general formula (4), and a structural unit (E) derived from a monomer represented by the following general formula (5). [In formula (1), R ａ and R ｂeach independently represents 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ R is selected from the group consisting of 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 contains one or more hetero ring atoms selected from O, N, and S and which may have a substituent; X represents a single bond or an optionally substituted fluorene group; A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms; 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, 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 - 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 ６１ and R ６２ , or R ７１ and R ７２ are bonded to each other to form a carbocyclic or heterocyclic ring having 1 to 20 carbon atoms, which may have a substituent; Ph represents a phenyl group; r and s each independently represent an integer of 0 to 5,000; 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 independently represents 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ R is selected from the group consisting of ｈrepresents 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 contains one or more hetero ring atoms selected from O, N, and S and which may have a substituent; X represents a single bond or 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; a and b each independently represent an integer of 0 to 10; R' and R'' each independently are selected from the group consisting of a hydrogen atom, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and an aryloxy group having 6 to 20 carbon atoms which may have a substituent. [In formula (4), R ｇ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. [In formula (5), G １ and G ２ each independently represents an alkylene group having 1 to 8 carbon atoms which may have a substituent, １ and K. ２ each independently represents a hydroxy group, an alkoxy group, or a halogen atom; R ｐ１ and R ｐ２ each independently represents a halogen atom, a cyano group, or an alkyl group having 1 to 8 carbon atoms which may have a substituent, １ and Ar ２ each independently represents a phenyl group or a naphthyl group which may have a substituent; １ and r ２ each independently represents an integer of 0 to 2; ３ and r ４ each independently represents an integer of 0 to 1.

[0012] According to the present invention, recycled resin can be produced from molding waste with excellent recycling efficiency and / or high quality.

[0013] 6A is a diagram schematically showing an embodiment of a mold; FIG. 6B is a diagram schematically showing an embodiment after injection molding; FIG. 6C is a diagram schematically showing an integrated product of a plastic product and molding waste obtained after injection molding; FIG. 6D is a diagram schematically showing a method for separating and collecting molding waste in a separating and collecting step of an embodiment; FIG. 6E is a diagram schematically showing a method for separating and collecting molding waste in a separating and collecting step of another embodiment; FIG. 6F is a diagram schematically showing a form in which the axial portions (sprue portions) of molding waste having an axial sprue portion 7 and a runner portion 8 are arranged in a misaligned manner, and FIG. 6G is a diagram schematically showing a form in which molding waste having a sprue portion 7 and a runner portion 8 are arranged in a unidirectional manner so that the axial portions (sprue portions 7) extend upward.

[0014] The meanings of terms used in this specification will be explained below, and the present invention will be described in detail.

[0015] As used herein, the term "halogen atom" refers to a fluorine atom (F), a chlorine atom (Cl), a bromine atom (Br), or an iodine atom (I).

[0016] 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 icosyl 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.

[0017] Examples of alkoxyl 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 icosyloxy groups. Examples of alkoxyl groups having 1 to 10 carbon atoms include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, and pentyloxy groups.

[0018] Examples of cycloalkyl groups having 5 to 20 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclododecyl group, a cyclotridecyl group, a cyclotetradecyl group, a cyclopentadecyl group, a cyclooctadecyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, etc. Examples of cycloalkyl groups having 5 to 10 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, etc.

[0019] Examples of cycloalkoxyl groups having 5 to 20 carbon atoms include cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclododecyloxy, cyclotridecyloxy, cyclotetradecyloxy, cyclopentadecyloxy, cyclooctadecyloxy, bicyclo[2.2.1]heptyloxy, bicyclo[2.2.2]octyloxy, etc. Examples of cycloalkyloxy groups having 5 to 10 carbon atoms include cyclopentyloxy, cyclohexyloxy, bicyclo[2.2.1]heptyloxy, bicyclo[2.2.2]octyloxy, etc.

[0020] Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a trimethylphenyl group, a tetramethylphenyl group, an ethylphenyl group, an ethylmethylphenyl group, a diethylphenyl group, a propylphenyl group, an isopropylphenyl group, an isopropylmethylphenyl group, a benzyl group, a phenethyl group, a phenylpropyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a naphthacenyl group, a chryserinyl group, a pyrenyl group, a biphenyl group, a terphenyl group, and a quaterphenyl group.

[0021] 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, benzofuranyl, isobenzofuranyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrazyl, pyrimidyl, pyridazyl, pyrrolidyl, indolyl, isoindolyl, indazolyl, quinolyl, isoquinolyl, naphthyridyl, quinoxalyl, and quinazolyl groups. Examples thereof include a pteridyl group, a phenanthridyl group, an acridinyl group, a pyrimidinyl group, a phenanthrolinyl group, a phenazinyl group, a thiophenyl group, a thiopyranyl group, a benzothiophenyl group, a benzothiopyranyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a furazanyl group, an oxadiazolyl group, a dithiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, and a benzisothiazolyl group.

[0022] Examples of the aryloxy group having 6 to 20 carbon atoms include a phenyloxy group, a tolyloxy group, a xylyloxy group, a trimethylphenyloxy group, a tetramethylphenyloxy group, an ethylphenyloxy group, an ethylmethylphenyloxy group, a diethylphenyloxy group, a propylphenyloxy group, an isopropylphenyloxy group, an isopropylmethylphenyloxy group, a naphthyloxy group, an anthracenyloxy group, a phenanthrenyloxy group, a naphthacenyloxy group, a chryserinyloxy group, a pyrenyloxy group, a biphenyloxy group, a terphenyloxy group, and a quaterphenyloxy group.

[0023] Examples of the alkyloxycarbonyl group having 2 to 10 carbon atoms include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, an isobutyloxycarbonyl group, a sec-butyloxycarbonyl group, and a tert-butyloxycarbonyl group.

[0024] Examples of the cycloalkyloxycarbonyl group having 5 to 10 carbon atoms include a cyclopentyloxycarbonyl group, a cyclohexyloxycarbonyl group, a bicyclo[2.2.1]heptyloxycarbonyl group, and a bicyclo[2.2.2]octyloxycarbonyl group.

[0025] Examples of the aryloxycarbonyl group having 7 to 15 carbon atoms include a phenyloxycarbonyl group, a tolyloxycarbonyl group, a xylyloxycarbonyl group, a trimethylphenyloxycarbonyl group, a tetramethylphenyloxycarbonyl group, an ethylphenyloxycarbonyl group, an ethylmethylphenyloxycarbonyl group, a diethylphenyloxycarbonyl group, and a naphthyloxycarbonyl group.

[0026] Examples of the alkylcarbonyloxy group having 2 to 10 carbon atoms include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, and a butylcarbonyloxy group.

[0027] Examples of the cycloalkylcarbonyloxy group having 5 to 10 carbon atoms include a cyclopentylcarbonyloxy group, a cyclohexylcarbonyloxy group, a bicyclo[2.2.1]heptylcarbonyloxy group, and a bicyclo[2.2.2]octylcarbonyloxy group.

[0028] Examples of the arylcarbonyloxy group having 7 to 15 carbon atoms include a phenylcarbonyloxy group, a tolylcarbonyloxy group, a xylylcarbonyloxy group, a trimethylphenylcarbonyloxy group, a tetramethylphenylcarbonyloxy group, an ethylphenylcarbonyloxy group, an ethylmethylphenylcarbonyloxy group, a diethylphenylcarbonyloxy group, and a naphthylcarbonyloxy group.

[0029] Examples of the hydroxyalkylcarbonyl group having 2 to 10 carbon atoms include a hydroxymethylcarbonyl group, a hydroxyethylcarbonyl group, and a hydroxypropylcarbonyl group.

[0030] Examples of the amide group having 1 to 10 carbon atoms include a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, and an acetylamino group.

[0031] <Method for Producing Recycled Resin> One aspect of the present invention relates to a method for producing recycled resin. The method includes a step of irradiating thermoplastic resin molding waste with laser light, identifying the type of thermoplastic resin in the molding waste based on Raman scattered light from the molding waste, and separating and recovering the molding waste (hereinafter also referred to as the "separation and recovery step"); and a step of obtaining recycled resin from the separated and recovered molding waste (hereinafter also referred to as the "recycled resin production step"). The method may optionally include a step of supplying a waste composition containing the molding waste to a vibrating conveying bed and vibratingly conveying the waste composition (hereinafter also referred to as the "vibration conveying step") prior to the separation and recovery step.

[0032] In the production method, the thermoplastic resin comprises at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by the following general formula (1), a structural unit (B) derived from a monomer represented by the following general formula (2), a structural unit (C) derived from a monomer represented by the following general formula (3), a structural unit (D) derived from a monomer represented by the following general formula (4), and a structural unit (E) derived from a monomer represented by the following general formula (5). In some embodiments, in the production method, the thermoplastic resin comprises at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by the following general formula (1), a structural unit (B) derived from a monomer represented by the following general formula (2), a structural unit (C) derived from a monomer represented by the following general formula (3), and a structural unit (D) derived from a monomer represented by the following general formula (4).

[0033] The present invention will be described below with reference to the drawings. Note that the drawings may be exaggerated for the purpose of explanation and may differ from the actual dimensions.

[0034] 1 is a diagram showing a schematic diagram of one embodiment of a mold. The mold 1 has a sprue 2, a runner 3, a gate 4, a cavity core 5, and cold slug wells 6 and 6'.

[0035] Molten resin is injected and poured into the mold 1 through the sprue 2. The inner diameter of the sprue 2 is circular and increases toward the inside of the mold 1. Therefore, the sprue 2 has a roughly truncated cone shape. The length of the sprue 2 usually depends on the distance to the runner 3, i.e., the thickness of the mold.

[0036] The molten resin injected from the sprue 2 passes through the runner 3, which branches into two. The length and inner diameter of the runner 3 are set taking into consideration the shape of the molded product, the properties of the molten resin, and the like. The runner 3 usually has a substantially cylindrical shape. Although the runner 3 in FIG. 1 branches into two, it may have only one runner without branching, or it may branch into three or more runners. When the molded product is small, from the viewpoint of manufacturing efficiency, the runner 3 preferably branches into three or more runners, more preferably 3 to 30 runners, even more preferably 3 to 25 runners, particularly preferably 3 to 20 runners, extremely preferably 3 to 10 runners, and most preferably 4 to 8 runners.

[0037] The molten resin that has passed through the runner 3 passes through the gate 4. The gate 4 has the function of controlling the injection speed of the molten resin into the cavity core 5. The inner diameter of the gate 4 is usually set smaller than the inner diameter of the runner 3, which allows the injection speed of the molten resin to be increased. In FIG. 1, the gate 4 is formed perpendicular to the runner 3, but it may also be formed parallel to the runner 3.

[0038] The molten resin that passes through the gate 4 is injected into the cavity core 5. Here, the cavity core 5 consists of a cavity, which is a recessed portion, and a core, which is a protruding portion. The molten resin is injected into the cavity (recessed portion) of the cavity core 5, and the cavity (recessed portion) and the core (protruding portion) join together to create a hollow portion that can be molded into the shape of the desired plastic product (molded body). Note that the cavity core 5 can have a so-called "nested structure" in which a pocket is machined in the mold 1 and a separately manufactured cavity and core are attached to the machined pocket.

[0039] Mold 1 has cold slug well 6 formed at the end of sprue 2 and cold slug well 6' formed at the end of the runner. Cold slug wells 6 and 6' function to prevent molding defects in plastic products by sealing in impurities, decomposition gases, etc. that may be contained in the tip of the molten resin.

[0040] After the molten resin is injected, the mold is cooled, solidifying the molten resin present in the sprue 2, runner 3, gate 4, cavity core 5, and cold slug wells 6 and 6' (cold runner method). Figure 2 is a schematic diagram showing one embodiment after injection molding. In Figure 2, the plastic product 11 has been separated from the molding waste and removed. Alternatively, the plastic product 11 and the molding waste may be removed together, and then the plastic product 11 may be separated.

[0041] As shown in Fig. 2, the portion of the molded body of solidified molten resin excluding the plastic product 11 is molding waste. In the embodiment shown in Fig. 2, the molding waste includes a sprue portion 7 derived from the sprue, a runner portion 8 derived from the runner, a gate portion 9 derived from the gate, and cold slug well portions 10 and 10' derived from the cold slug well.

[0042] Figure 3 is a schematic diagram of a united product of a plastic product and molding waste obtained after injection molding. The molding waste is a plastic product 11 separated from the united product, and includes a sprue portion 7, eight runner portions 8 with a branched structure, a gate portion 9, and a cold slug well portion 10 at the end of the sprue portion. In this embodiment, the united product has a gate portion 9 formed at the end of the runner portion 9, and a plastic product 11 formed at the tip of the gate portion 9. The molding waste shown in Figure 3 includes an axial sprue portion 7, eight leg-shaped (branched) runner portions 8 extending evenly circumferentially from below the shaft, gate portions 9 at the tips of the runner portions 8, and a cold slug well portion 10 at the end of the sprue portion 7.

[0043] (Molding waste) Molding waste refers to the portion of a molded body generated during the molding process of a thermoplastic resin, excluding the product (for example, the plastic product 11 shown in Figures 2 and 3). Therefore, molding waste is composed of a thermoplastic resin. Molding waste may be composed of one type of thermoplastic resin, or may be composed of two or more types of thermoplastic resin. The type and combination of thermoplastic resins that make up the molding waste can be determined depending on the physical properties of the desired plastic product (molded body).

[0044] In some embodiments, molding waste is discarded after molding optical materials. In some embodiments, molding waste is discarded after molding optical lenses.

[0045] The molding waste includes at least one selected from the group consisting of a sprue portion, a runner portion, a gate portion, and a cold slug well portion. Note that at least one of the sprue portion, the runner portion, the gate portion, and the cold slug well portion may be broken or otherwise dropped off from the molding waste due to mechanical impacts such as those caused by collection, transportation, and mixing of the molding waste.

[0046] In some embodiments, the molding waste comprises one, two, three, or four selected from the group consisting of a sprue portion, a runner portion, a gate portion, and a cold slug well portion. In one embodiment, the molding waste comprises a sprue portion and / or a runner portion. In one embodiment, the molding waste comprises a sprue portion and / or a runner portion. In one embodiment, the molding waste comprises a sprue portion, a runner portion, and a gate portion. In one embodiment, the molding waste comprises a sprue portion, a runner portion, and a cold slug well portion. In one embodiment, the molding waste comprises a sprue portion, a runner portion, a gate portion, and a cold slug well portion. In these embodiments, the molding waste is discharged after molding an optical material (preferably an optical lens). Note that the molding waste composition may contain molding waste of different shapes. Note that, in this specification, the term "comprises" is intended to allow for other configurations, and is synonymous with, for example, "includes."

[0047] As used herein, the term "sprue portion" refers to a portion having a shape derived from the sprue (flow path for molten resin) within a mold. As used herein, "molten resin" refers to resin in a molten state. The shape of the sprue portion is not particularly limited, but a truncated cone is preferred. 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), and the like, but is preferably 0.1 to 10 mm, more preferably 1 to 8 mm, and even more preferably 1 to 6 mm. In this specification, the term "inner diameter" refers to the maximum distance between two points on the contour line of a cross section perpendicular to the longitudinal direction of an object. For example, if the shape of the sprue portion is a truncated cone, the maximum inner diameter corresponds to the "inner diameter."

[0048] The length of the sprue portion (corresponding to the height of the truncated cone when the sprue is shaped like a truncated cone) is preferably 0.1 to 200 mm, more preferably 1 to 100 mm, and even more preferably 1 to 50 mm.

[0049] In this specification, the term "runner portion" refers to a portion having a shape derived from a runner (a flow path for molten resin) in a mold. When molding waste has a runner portion, the molding waste becomes more likely to become entangled with each other. The shape of the runner portion is preferably cylindrical. Furthermore, the runner portion may have a shape that branches in two or more directions, preferably two or three directions, along the way. The runner portion is preferably formed perpendicular to the length of the sprue portion. This can prevent molding defects. However, forming a runner portion perpendicular to the length of the sprue portion can be a factor that makes molding waste more likely to become entangled with each other. Furthermore, as described above, the mold may have a structure in which the molten resin injected from the sprue flows in two or more directions due to the branched runners. Therefore, molding waste may have two or more runner portions. In one embodiment, the molding waste preferably has three or more runners, more preferably 3 to 30 runners, even more preferably 3 to 25 runners, particularly preferably 3 to 20 runners, extremely preferably 3 to 10 runners, and most preferably 4 to 8 runners. The inner diameter of the runners varies depending on the physical properties of the molten resin used, the shape of the desired plastic product (molded article), and the like, 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 runners (equivalent to the height of the cylinder if it is cylindrical) is preferably 0.1 to 200 mm, more preferably 1 to 100 mm, and even more preferably 1 to 50 mm.

[0050] In this specification, the term "gate portion" refers to a portion having a shape derived from a gate (a flow path for molten resin) in a mold. The shape of the gate portion is not particularly limited and can be set appropriately depending on the physical properties of the molten resin used, the shape of the desired plastic product (molded article), and the like. The inner diameter of the gate portion varies depending on the physical properties of the molten resin used, the shape of the desired plastic product (molded article), and the like, but is preferably 0.1 to 5 mm, more preferably 0.1 to 3 mm, and even more preferably 0.1 to 2 mm. The inner diameter of the gate portion is preferably smaller than the inner diameter of the runner portion. The length of the gate portion is also not particularly limited and can be set appropriately depending on the physical properties of the molten resin used, the shape of the desired plastic product (molded article), and the like.

[0051] As used herein, the term "cold slug well" refers to a portion having a shape derived from the cold slug well (a portion containing molten resin containing impurities, decomposition gases, etc.) within a mold. The shape of the cold slug well is not particularly limited, but is preferably a test tube, a truncated cone, or a cylindrical shape. The inner diameter of the cold slug well varies depending on the physical properties of the molten resin used and the shape of the desired plastic product (molded article), but is preferably 0.1 to 10 mm, more preferably 1 to 8 mm, when the gate is formed at the end of the sprue. Furthermore, the inner diameter of the cold slug well is preferably 0.1 to 5 mm, more preferably 1 to 4 mm, when the gate is formed at the end of the runner. The length of the cold slug well is not particularly limited, but is preferably 0.1 to 20 mm, more preferably 0.1 to 10 mm.

[0052] In addition to the thermoplastic resin, the molding waste may contain resins other than the thermoplastic resin, additives, decomposition products thereof, etc. In this specification, "resin" means a resin having a weight average molecular weight of 1000 or more. The content of the thermoplastic resin in the molding waste is usually 80% by weight or more, preferably 85% by weight or more, more preferably 90% by weight or more, even more preferably 95% by weight or more, even more preferably 98% by weight or more, and particularly preferably 100% by weight, based on the total weight of the molding waste.

[0053] (Waste composition) In this specification, the waste composition includes two or more molding waste products. The waste composition includes molding waste products generated during the manufacturing process of a molded body. In addition, the waste composition may further include molded products recovered after being used on the market as part of a product, defective products generated in the molding process, defective products generated in the commercialization process, unused molded products that are no longer needed, etc. The content of molding waste products in the waste composition is preferably 30% by mass or more, more preferably 40% by mass or more, even more preferably 50% by mass or more, and particularly preferably 50 to 100% by mass, relative to the total mass of the waste composition.

[0054] The waste composition may be made by collecting molding waste from the same lot, or by collecting molding waste from different lots and combining these.

[0055] (Thermoplastic resin) The thermoplastic resin constituting the molding waste is not particularly limited and may be a polyester resin, a polycarbonate resin, a polyester carbonate resin, an epoxy resin, a polyurethane resin, a polyacrylic acid ester resin, a polymethacrylic acid ester resin, or the like, but is preferably a polycarbonate resin, a polyester carbonate resin, or a polyester resin, and more preferably a polycarbonate resin.

[0056] In the present invention, the thermoplastic resin constituting the molded waste contains at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by the following general formula (1), a structural unit (B) derived from a monomer represented by the following general formula (2), a structural unit (C) derived from a monomer represented by the following general formula (3), a structural unit (D) derived from a monomer represented by the following general formula (4), and a structural unit (E) derived from a monomer represented by the following general formula (5). In some embodiments, the thermoplastic resin constituting the molded waste contains at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by the following general formula (1), a structural unit (B) derived from a monomer represented by the following general formula (2), a structural unit (C) derived from a monomer represented by the following general formula (3), and a structural unit (D) derived from a monomer represented by the following general formula (4).

[0057] For example, when the thermoplastic resin is a polycarbonate resin, it contains at least one selected from the structural unit (A), the structural unit (B), and the structural unit (D).

[0058] For example, when the thermoplastic resin is a polyester resin or a polyester carbonate resin, it contains at least one selected from the structural unit (A), the structural unit (B), the structural unit (C), the structural unit (D), and the structural unit (E). Alternatively, when the thermoplastic resin is a polyester resin or a polyester carbonate resin, it contains at least one selected from the structural unit (A), the structural unit (B), the structural unit (C), and the structural unit (D).

[0059] In some embodiments, the thermoplastic resin is a resin having the structural unit (C) derived from the monomer represented by the above formula (3) and / or the structural unit (E) derived from the monomer represented by the above formula (5), and is usually a resin (e.g., a polyester resin) containing a structural unit derived from a dihydroxy compound (diol) together with the structural unit (E). Examples of the dihydroxy compound (diol) include the structural unit (A), structural unit (B), and structural unit (D) derived from the dihydroxy compound (diol) represented by the above formula (1), formula (2), and / or formula (4), and / or a structural unit derived from a dihydroxy compound (diol) from which other structural units described below are derived.

[0060] (1) Structural Unit (A) In some embodiments, the thermoplastic resin contains a structural unit (A) derived from a monomer represented by the following general formula (1): The structural unit (A) may be contained alone, or two or more types may be contained in combination.

[0061] In formula (1), R ａ and R ｂ each independently represents 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent. ａ and R ｂis preferably a hydrogen atom, 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom, or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom, or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0062] In formula (1), X represents a single bond or an optionally substituted fluorene group, preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms.

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

[0064] In formula (1), m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 3, and more preferably 0 or 1.

[0065] In formula (1), a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, and more preferably 1 or 2.

[0066] In the formula (1), the substituent "may have a substituent" is not particularly limited, and examples thereof include a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkoxyl group having 5 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, a cycloalkyloxycarbonyl group having 5 to 10 carbon atoms, an aryloxycarbonyl group having 7 to 15 carbon atoms, an alkylcarbonyloxy group having 2 to 10 carbon atoms, a cycloalkylcarbonyloxy group having 5 to 10 carbon atoms, an arylcarbonyloxy group having 7 to 15 carbon atoms, a hydroxyalkylcarbonyl group having 2 to 10 carbon atoms, a glycidyloxycarbonyl group, a hydroxy group, a carboxy group, a cyano group, and an amide group having 1 to 10 carbon atoms.

[0067] Specific examples of the structural unit (A) include structural 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)naphthalen-2-yl]fluorene (also referred to as "BNEF"), 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene, etc. In one embodiment, the structural unit (A) includes at least one structural unit derived from BNE, DP, and BNEF.

[0068] (2) Structural Unit (B) In some embodiments, the thermoplastic resin contains a structural unit (B) derived from a monomer represented by the following general formula (2): The structural unit (B) may be contained alone or in combination of two or more types.

[0069] In formula (2), R ｃ and R ｄ are each independently selected from the group consisting of 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. ｃ and R ｄ is preferably a hydrogen atom, 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom, or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom, or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0070] In formula (2), Y represents a single bond, a fluorene group which may have a substituent, or —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 Y is preferably a single bond or -CR ２１ R ２２ - is. 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 ６１ and R ６２ , or R ７１ and R ７２ are bonded to each other to form a carbon ring or hetero ring having 1 to 20 carbon atoms, which may have a substituent. Ph represents a phenyl group. r and s each independently represent an integer of 0 to 5,000.

[0071] In formula (2), A and B each independently represent an alkylene group having 1 to 5 carbon atoms 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, and preferably an alkylene group having 2 or 3 carbon atoms.

[0072] In formula (2), p and q each independently represent an integer of 0 to 4, preferably 0 or 1.

[0073] In formula (2), a and b each independently represent an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, for example, 0 or 1.

[0074] In the formula (2), the substituent "may have a substituent" is not particularly limited, and examples thereof include a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkoxyl group having 5 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, a cycloalkyloxycarbonyl group having 5 to 10 carbon atoms, an aryloxycarbonyl group having 7 to 15 carbon atoms, an alkylcarbonyloxy group having 2 to 10 carbon atoms, a cycloalkylcarbonyloxy group having 5 to 10 carbon atoms, an arylcarbonyloxy group having 7 to 15 carbon atoms, a hydroxyalkylcarbonyl group having 2 to 10 carbon atoms, a glycidyloxycarbonyl group, a hydroxy group, a carboxy group, a cyano group, and an amide group having 1 to 10 carbon atoms.

[0075] Specific examples of the structural unit (B) include 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (also referred to as "BCFL"), 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (also referred to as "BPEF"), 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene (also referred to as "BPPEF"), 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-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 referred to 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 referred to 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), 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',In one embodiment, the structural unit (B) includes at least one structural unit derived from BPEF, BPPEF, BPA, BPM, and BCFL.

[0076] (3) Structural Unit (C) In some embodiments, the thermoplastic resin contains a structural unit derived from a monomer represented by the following general formula (3): The structural unit (C) may be contained alone, or two or more types may be contained in combination.

[0077]

[0078] In formula (3), R ａ and R ｂ each independently represents 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent. ａ and R ｂ is preferably a hydrogen atom, 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 contains one or more hetero ring atoms selected from O, N and S and which may have a substituent, more preferably a hydrogen atom, or an aryl group having 6 to 20 carbon atoms which may have a substituent, and even more preferably a hydrogen atom, or an aryl group having 6 to 12 carbon atoms which may have a substituent.

[0079] In formula (3), X represents a single bond or an optionally substituted fluorene group, preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms.

[0080] In formula (3), A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have a substituent, and preferably an alkylene group having 2 or 3 carbon atoms.

[0081] In formula (3), m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 3, and more preferably 0 or 1.

[0082] In formula (3), a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, and more preferably 1 or 2.

[0083] In formula (3), R' and R'' are each independently selected from the group consisting of a hydroxy group, a halogen atom, an alkoxy group having 1 to 20 carbon atoms which may have a substituent, and an aryloxy group having 6 to 20 carbon atoms which may have a substituent. R' and R'' are preferably a hydroxy group, a linear alkoxy group having 1 to 5 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, and more preferably a hydroxy group, a methoxy group, an ethoxy group, or a phenyloxy group.

[0084] In the formula (3), the substituent "may have a substituent" is not particularly limited, and examples thereof include a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkoxyl group having 5 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, a cycloalkyloxycarbonyl group having 5 to 10 carbon atoms, an aryloxycarbonyl group having 7 to 15 carbon atoms, an alkylcarbonyloxy group having 2 to 10 carbon atoms, a cycloalkylcarbonyloxy group having 5 to 10 carbon atoms, an arylcarbonyloxy group having 7 to 15 carbon atoms, a hydroxyalkylcarbonyl group having 2 to 10 carbon atoms, a glycidyloxycarbonyl group, a hydroxy group, a carboxy group, a cyano group, and an amide group having 1 to 10 carbon atoms.

[0085] Specific examples of the structural unit (C) include those derived from 2,2'-([1,1'-binaphthalene]-2,2'-diylbis(oxy))acetoacetic acid (BINOL-DC) and its methyl ester, ethyl ester, phenyl ester, etc. In one embodiment, the structural unit (C) includes at least one structural unit derived from BINOL-DC and its methyl ester, ethyl ester, or phenyl ester.

[0086] (4) Structural Unit (D) In ​​some embodiments, the thermoplastic resin contains a structural unit (D) derived from a monomer represented by the following general formula (4): The structural unit (D) may be contained alone, or two or more types may be contained in combination.

[0087] In formula (4), R ｇ Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. ｇ are each preferably independently a hydrogen atom.

[0088] Specific examples of the structural unit (D) include structural units derived from decahydro-1,4:5,8-dimethanonaphthalene diols (also referred to as "D-NDM"). Examples include 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, and (2-ethyldecahydro-1,4:5,8-dimethanonaphthalene-2,7-diyl)dimethanol. In one embodiment, the structural unit (D) comprises at least one structural unit derived from D-NDM.

[0089] (5) Structural Unit (E) In some embodiments, the thermoplastic resin contains a structural unit (E) derived from a monomer represented by the following general formula (5): The structural unit (E) may be contained alone, or two or more types may be contained in combination.

[0090] In formula (5), G １ and G ２ Each of the groups independently represents an alkylene group having 1 to 8 carbon atoms, which may have a substituent. Examples of the alkylene group having 1 to 8 carbon atoms include methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, and pentylene. Among these, G １ and G ２ 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.

[0091] In formula (5), K １ and K. ２ each independently represents a hydroxy group, an alkoxy group, or a halogen atom. １ and K. ２ When is an alkoxy group, the number of carbon atoms therein is not particularly limited, and it is, for example, an alkoxy group having 1 to 20 carbon atoms.

[0092] In formula (5), R ｐ１ and R ｐ２ Each of Ar and Ar independently represents a halogen atom, a cyano group, or an alkyl group having 1 to 8 carbon atoms which may have a substituent. １ and Ar ２ Each of r independently represents a phenyl group or a naphthyl group which may have a substituent. １ and r ２ Each independently represents an integer of 0 to 2, preferably 0 to 1. In formula (5), r ３ and r ４ each independently represents an integer of 0 to 1.

[0093] In the formula (5), the substituent "may have a substituent" is not particularly limited, and examples thereof include a halogen atom, a hydroxy group, a carboxy group, a cyano group, etc. These substituents may be present alone or in combination of two or more.

[0094] In some embodiments, the thermoplastic resin preferably includes 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 a 9,9-bis(carboxyalkyl)fluorene, and in the above formula (5), r ３ and r ４ The general formula (5-2) is a 9,9-bis(carboxyalkyl)-diarylfluorene, and r ３ and r ４ is 1, and Ar １ and Ar ２ is a structural unit derived from a monomer in which r is a phenyl group. ３ and r ４ is 1, and Ar １ and Ar ２ is a structural unit derived from a monomer in which the group is a naphthyl group.

[0095] In the formulas (5-1), (5-2), and (5-3), G １ and G ２ , R ｐ１ and R ｐ２ , r １ and r ２ is defined as in equation (5).

[0096] Specific examples of monomers from which the structural unit represented by formula (5-1) is derived include 9,9-bis(carboxy C2-6 alkyl)fluorenes, preferably 9,9-bis(carboxy C2-4 alkyl)fluorenes, more preferably 9,9-bis(carboxy C2-3 alkyl)fluorenes, as well as alkyl esters and acid halides thereof. Examples include 9,9-bis(2-carboxyethyl)fluorene, 9,9-bis(2-carboxypropyl)fluorene, as well as alkyl esters and acid halides thereof, preferably 9,9-bis(2-carboxyethyl)fluorene, as well as alkyl esters and acid halides thereof. 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.

[0097] Specific examples of monomers from which the structural unit represented by formula (5-2) is derived include 9,9-bis(carboxy C2-6 alkyl)-diphenylfluorenes, preferably 9,9-bis(carboxy C2-4 alkyl)-diphenylfluorenes, and more preferably 9,9-bis(carboxy C2-3 alkyl)-diphenylfluorenes, as well as alkyl esters and acid halides thereof. Examples include 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, and 9,9-bis(2-carboxypropyl)-2,7-diphenylfluorene, as well as alkyl esters and acid halides thereof. In the case of alkyl esters, the alkyl group is not particularly limited and may be, for example, an alkyl group having 1 to 20 carbon atoms.

[0098] Specific examples of monomers that derive the structural unit represented by formula (5-3) include structural units derived from 9,9-bis(carboxyC2-6 alkyl)-dinaphthylfluorenes. In this case, the compound that derives the structural unit may be an alkyl ester, an acid halide, or an acid anhydride. Examples of structural units include those derived from 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, alkyl esters thereof, and acid halides thereof. 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.

[0099] In some embodiments, the structural unit (E) includes structural units derived from 9,9-bis(2-carboxyethyl)fluorene, its alkyl esters having 1 to 20 carbon atoms (preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms), and acid halides. In certain embodiments, the structural unit (E) includes structural units derived from 9,9-bis(2-carboxyethyl)fluorene.

[0100] The structural unit (A), the structural unit (B), the structural unit (C), the structural unit (D), and the structural unit (E) may be contained alone in the resin, or two or more types may be contained in combination.

[0101] (6) Other Structural Units The resin may further contain, in addition to the above-described structural units, structural units of other polycarbonate resins, or structural units of other resins (polyester resins, polyester carbonate resins, polyolefin resins), etc.

[0102] For example, other structural units of polycarbonate resins include structural units derived from dihydroxy compounds (diols) such as 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-1-ol) (DBHBNABHP) represented by the following formulas; 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.

[0103] Further, examples of the structural units of polyester resins or polyester carbonate resins include structural units derived from dicarboxylic acids or ester derivatives thereof, 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 (for example, 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 structural units derived from dihydroxy compounds (diols) that constitute polyester resins or polyester carbonate resins include structural units derived from dihydroxy compounds (diols) such as 2,2'-[1,4-phenylenebis(methyleneoxy[1,1'-binaphthalene]-2',2-diyloxy)]di(ethan-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.

[0104] In some embodiments, the lower the content of these other structural units, the better; for example, it is preferably 50% by weight or less, more preferably 30% by weight or less, and even more preferably 10% by weight or less, based on the total weight of the thermovisible resin constituting the molding waste.

[0105] In some embodiments, the content of the thermoplastic resin containing at least one selected from the structural unit (A), the structural unit (B), the structural unit (C), the structural unit (D), and the structural unit (E) is preferably 80% by mass or more, more preferably 80 to 99% by mass, based on the total mass of the waste composition. A resin content of 80% by mass or more is preferred because it increases recycling efficiency. In some embodiments, the content of the thermoplastic resin containing at least one selected from the structural unit (A), the structural unit (B), the structural unit (C), and the structural unit (D) is preferably 80% by mass or more, more preferably 80 to 99% by mass, based on the total mass of the waste composition. A resin content of 80% by mass or more is preferred because it increases recycling efficiency.

[0106] In some embodiments, the thermoplastic resin constituting the molding waste preferably includes at least one selected from the group consisting of a resin composed of the structural unit (A) and the structural unit (B), a resin composed of the structural unit (B) and the structural unit (C), a resin composed of the structural unit (B) and the structural unit (D), a resin composed of the structural unit (A), a resin composed of the structural unit (B), a resin composed of the structural unit (C), and a resin composed of the structural unit (D). Such resins are excellent in terms of optical properties such as refractive index.

[0107] In some embodiments, the thermoplastic resin constituting the molding waste is represented by any one of the following formulas (I-1), (I-2), (I-3), (II-1), (II-2), (II-3), (II-4), (II-5), and (II-6). Such resins are excellent in terms of optical properties such as refractive index. In the formula, x, y, and z represent the number of repeating units. There are no particular limitations on x, y, and z, and they may be determined depending on the desired molecular weight and monomer ratio. x, y, and z are each independently an integer of, for example, 1 to 100, and preferably an integer of 1 to 10.

[0108] The weight average molecular weight (Mw) of the thermoplastic resin containing at least one selected from the structural unit (A), the structural unit (B), the structural unit (C), and the structural unit (D) 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 product, 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)" refers to the weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0109] In some embodiments, the thermoplastic resin constituting the molding waste is a resin (e.g., a polyester resin) containing a structural unit (E) derived from a monomer represented by the above formula (5) (e.g., at least one structural unit selected from the group consisting of the above formulas (5-1), (5-2), and (5-3)) and a structural unit derived from a dihydroxy compound (diol). Examples of the dihydroxy compound (diol) include the structural unit (A), structural unit (B), and structural unit (D) derived from a dihydroxy compound (diol) represented by the above formula (1), formula (2), and / or formula (4), and / or a structural unit derived from a dihydroxy compound (diol) from which other structural units described below are derived. Furthermore, the thermoplastic resin may further contain structural units such as other resins (polyester resins, polyester carbonate resins, polyolefin resins) in addition to the structural unit (E) derived from a monomer represented by the above formula (5) (e.g., at least one structural unit selected from the group consisting of the above formulas (5-1), (5-2), and (5-3)) and the structural unit derived from the dihydroxy compound (diol).

[0110] In some embodiments, the thermoplastic resin constituting the molded waste contains a constitutional unit derived from 9,9-bis(2-carboxyethyl)fluorene (or an ester or acid halide thereof). For example, the thermoplastic resin constituting the molded waste may be a resin containing at least one constitutional unit selected from the group consisting of formulas (iii-a1) to (iii-a5).

[0111]

[0112] Of the structural units represented by the above formulas (iii-a1) to (iii-a6), formulas (iii-a1) and (iii-a2) are structural units derived from dicarboxylic acids (or their esters, acid halides), formulas (iii-a3), (iii-a4), (iii-a5), and (iii-a6) are structural units derived from dihydroxy compounds (diols), and the structural unit represented by formula (iii-a1) is a structural unit derived from 9,9-bis(2-carboxyethyl)fluorenes (or their esters or acid halides).

[0113] For example, the thermoplastic resin is selected from the group consisting of the following (III-1), (III-2), and (III-3): Such resins are excellent in terms of optical properties such as refractive index.

[0114] (III-1) Resin containing a structural unit represented by formula (iii-a1), a structural unit represented by formula (iii-a2), a structural unit represented by formula (iii-a3), and a structural unit represented by formula (iii-a4). In some embodiments, the thermoplastic resin is a polyester resin in which an ester bond is formed between the structural unit represented by formula (iii-a1) and the structural unit represented by formula (iii-a2) and the structural unit represented by formula (iii-a3) and the structural unit represented by formula (iii-a4). The ratio of each structural unit is not particularly limited. Other structural units may also be included. In one embodiment, the thermoplastic resin is a copolymer polyester resin obtained from naphthalene dicarboxylic acid, BPEF, fluorene dipropionate, and ethylene glycol.

[0115] (III-2) Resin containing a structural unit represented by formula (iii-a1), a structural unit represented by formula (iii-a2), a structural unit represented by formula (iii-a4), and a structural unit represented by formula (iii-a5). In some embodiments, the thermoplastic resin is a polyester resin in which an ester bond is formed between the structural unit represented by formula (iii-a1) and the structural unit represented by formula (iii-a2) and the structural unit represented by formula (iii-a4) and the structural unit represented by formula (iii-a5). The ratio of each structural unit is not particularly limited. Other structural units may also be included. In one embodiment, the thermoplastic resin is a copolymer polyester resin obtained from naphthalene dicarboxylic acid, BPPEF, fluorene dipropionate, and ethylene glycol.

[0116] (III-3) Resin containing a structural unit represented by formula (iii-a1), a structural unit represented by formula (iii-a4), and a structural unit represented by formula (iii-a6). In some embodiments, the thermoplastic resin is a polyester resin in which an ester bond is formed between the structural unit represented by formula (iii-a1), the structural unit represented by formula (iii-a4), and the structural unit represented by formula (iii-a6). The ratio of each structural unit is not particularly limited. Other structural units may also be included. In one embodiment, the thermoplastic resin is a copolymer polyester resin obtained from BNEF, fluorenedipropionic acid ester, and ethylene glycol. In another embodiment, the thermoplastic resin is a copolymer polyester resin obtained from BNEF, BPEF, fluorenedipropionic acid ester, and ethylene glycol.

[0117] The weight-average molecular weight (Mw) of the resins (III-1) to (III-3) 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 product, such as a resin for an optical lens. 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.

[0118] (Additives / Decomposition Products) The additives constituting the molding waste are not particularly limited, and known additives can be used. In addition, decomposition products of the resins constituting the molding waste include, for example, monomers, dimers, copolymers, oligomers of resins or impurity resins having at least one structural unit (A) to (E) selected from the group consisting of general formulas (1) to (5), aryl alcohols such as phenol, carbonate diesters such as diphenyl carbonate, monomer-modified products such as those represented by the following formulas (A-1) and (A-2), and resin-modified products having partial structures represented by the following formulas (B-1) and (B-2).

[0119] Each step will be described in detail below. In some embodiments, the method for producing recycled resin includes optional steps of a vibration transport step, a sorting and recovery step, and a recycled resin production step.

[0120] 1. Vibration Conveying Step The vibration conveying step is a step of supplying a waste composition containing molded waste products to a vibration conveying bed and vibratingly conveying the waste composition.

[0121] For example, if molding waste has a structure that is prone to entanglement, such as a runner portion, it may be prone to entanglement, and when an attempt is made to feed a waste composition containing entangled molding waste into a crusher, this can cause problems in feeding the waste into the crusher, resulting in low recycling efficiency. In such cases, by undergoing a vibration transport process before the sorting and recovery process, it is possible to eliminate or reduce the entanglement of the molding waste, and as a result, it is possible to produce recycled resin from molding waste with excellent recycling efficiency.

[0122] The vibration transport step is an optional step that is performed as needed, and can be omitted if the entanglement of the molding waste is small or non-existent. If the molding waste has a runner part, it is desirable to perform the vibration transport step before the sorting and recovery step.

[0123] (Vibrating conveying bed) The vibrating conveying bed is not particularly limited as long as it can eliminate or reduce the entanglement between the formed waste products contained in the waste composition by vibrating and conveying the waste composition. Specifically, the vibrating conveying bed may be a plate-like member, a conveyor, a turntable, or any other shape, but is preferably a plate-like member or a conveyor, and more preferably a conveyor. In this case, the size of the vibrating conveying bed can be appropriately set. In addition, the vibrating conveying bed may be installed parallel to the horizontal plane or at an incline.

[0124] When the vibrating conveying bed is a plate-like member or a conveyor, the width of the vibrating conveying bed is preferably 5 cm to 5 m, more preferably 10 cm to 3 m, and even more preferably 20 cm to 1 m. The length of the vibrating conveying bed is preferably 50 cm to 30 m, more preferably 1 to 10 m, and even more preferably 1 to 5 m.

[0125] The vibrating transport floor is usually provided with a vibration mechanism (for example, an induction motor, a resonator, a vibration motor, etc.).

[0126] In addition, the vibrating conveying bed may further be provided with a feeder for supplying the waste composition to the vibrating conveying bed, a vibration control mechanism (constant drive, intermittent drive, variable speed drive, etc.) for controlling the vibration mechanism, a discharge mechanism for removing the waste composition after the vibrating conveying bed, etc.

[0127] (Vibration Conveyance) By vibrating and transporting the waste composition on a vibrating transport bed, entanglement between the molded waste materials contained in the waste composition can be eliminated or reduced.

[0128] The vibration frequency of the vibrating conveying bed is preferably 1 to 1000 Hz, more preferably 5 to 500 Hz, even more preferably 10 to 100 Hz, and even more preferably 30 to 80 Hz. When the vibration frequency of the vibrating conveying bed is within the above range, entanglement is easily eliminated, energy consumption is reduced, and operating efficiency is good, which is preferable.

[0129] The supply amount of the waste composition relative to the width of the vibrating conveying bed is preferably 100 to 5000 g / m, more preferably 100 to 2000 g / m, and from the viewpoint of effectively eliminating or reducing entanglement, is further preferably 100 to 1500 g / m, particularly preferably 100 to 1000 g / m, and from the viewpoint of high production efficiency, is most preferably 500 to 1000 g / m.

[0130] The feed rate of the waste composition to the vibrating conveying bed is preferably 5 to 100 g / sec, more preferably 5 to 60 g / sec, more preferably 5 to 40 g / sec from the viewpoint of effectively eliminating or reducing entanglement, and even more preferably 15 to 40 g / sec from the viewpoint of production efficiency.

[0131] In one embodiment, the supply amount of the waste composition relative to the width of the vibrating conveying bed is preferably 100 to 2000 g / m, and the supply rate of the waste composition to the vibrating conveying bed is preferably 5 to 40 g / sec, more preferably 100 to 1500 g / m, and the supply rate is preferably 5 to 40 g / sec, and even more preferably 500 to 1000 g / m, and the supply rate is preferably 15 to 40 g / sec.

[0132] The specific gravity of the molding waste is preferably 0.9 to 1.5, more preferably 0.9 to 1.4, even more preferably 1.0 to 1.4, still more preferably 1.0 to 1.3, and particularly preferably 1.1 to 1.3. If the specific gravity of the molding waste is within the above range, it is preferable because entanglement between the molding waste products can be easily eliminated or reduced by vibration transport.

[0133] 2. Sorting and Recovery Step The sorting and recovery step is a step of irradiating laser light onto molding waste products made of thermoplastic resin, identifying the type of thermoplastic resin in the molding waste products based on Raman scattered light scattered from the molding waste products, and sorting and recovering the molding waste products.

[0134] When recycling waste molding products of thermoplastic resins, the resulting waste molding products are recovered and collected, and the resulting waste composition is recycled. While it is desirable to recover waste molding products by resin type, waste compositions may contain a mixture of multiple resins. As a result, attempting to recycle the waste composition as is may result in reduced recycling efficiency and reduced quality of the recycled resin. According to the separation and recovery process of this embodiment, the waste molding products are separated and recovered by type and grade of thermoplastic resin using a simple method using laser light before recycling. As a result, excellent recycling efficiency and / or production of high-quality recycled resin are possible. Therefore, another aspect of the present invention also relates to a method for separating and recovering waste molding products made of thermoplastic resins, including the separation and recovery process. That is, one embodiment of the present invention provides a method for separating and recovering molding waste, which comprises the steps of irradiating a molding waste made of a thermoplastic resin with a laser beam, identifying the type of thermoplastic resin in the molding waste based on the Raman scattered light scattered from the molding waste, and separating and recovering the molding waste, wherein the thermoplastic resin comprises at least one selected from the group consisting of a structural unit (A) derived from a monomer represented by the general formula (1), a structural unit (B) derived from a monomer represented by the general formula (2), a structural unit (C) derived from a monomer represented by the general formula (3), a structural unit (D) derived from a monomer represented by the general formula (4), and a structural unit (E) derived from a monomer represented by the general formula (5). In the separation and recovery method of this embodiment, the vibration transport step may be carried out before the separation and recovery step.

[0135] 4 is a diagram showing a method for separating and collecting molding waste in a separating and collecting step according to an embodiment of the present invention. As shown in FIG. 4, the separating and collecting of molding waste begins with identifying the types of thermoplastic resins that make up the molding waste 12, and then, based on the identification results, the molding waste 12 is separated and collected by type of thermoplastic resin.

[0136] The separating and collecting step is preferably carried out continuously on a conveyor. For example, as shown in Fig. 4, molding waste 12 made of thermoplastic resin is supplied onto a conveyor such as a belt conveyor 16, and the separating and collecting step is carried out continuously on the belt conveyor 16. The conveyor is not particularly limited as long as it can transport molding waste 12, and in addition to a belt conveyor, a belt loader or the like can be used.

[0137] The molding waste 12 is preferably supplied at equal intervals onto the conveyor. Supplying the molding waste 12 at equal intervals can improve the accuracy of identifying and separating and recovering the thermoplastic resin. The molding waste 12 is preferably supplied individually onto the conveyor in an untangled state. If the molding waste 12 are entangled with each other, it is preferable to perform the vibration transport process or the like to untangle the molding waste and then perform the separation and recovery process. The supplying of the molding waste 12 at equal intervals onto the conveyor is performed, for example, by a system (e.g., an arm-type robot, a picking robot) that places the untangled molding waste onto the conveyor at equal intervals after the vibration transport process.

[0138] The molding scrap 12 are preferably supplied onto the conveyor with their shapes aligned. Arranging them in a uniform shape reduces or prevents misrecognition. For example, as shown in FIG. 3 , the molding scrap 12 includes an axial sprue portion 7 and two or more runner portions 8 extending evenly circumferentially from below the axis of the sprue portion 7. Such molding scrap 12 including the axial sprue portion 7 and the branched runner portions 8 has a substantially T-shape when viewed from the side. Such substantially T-shaped molding scrap 12 are preferably arranged on the conveyor with their shapes aligned in an inverted T-shape, as shown in FIG. 6B . Specifically, the molding scrap 12 are preferably arranged on the conveyor with their shapes aligned so that the tip of the axial sprue portion 7 faces upward. Arranging the molding scrap 12 in a uniform direction allows the laser light to be focused, improving the recognition rate and achieving a recognition rate close to 100%. On the other hand, if the molding scrap 12 are arranged randomly without being aligned, the focus may be lost, resulting in reduced recognition accuracy. As shown in FIG. 6B , the molding scrap 12 is preferably arranged so that the runner portion 8, which has a branched structure and extends evenly in the circumferential direction, contacts the conveyor. This arrangement stably places the molding scrap 12 on the conveyor, preventing the molding scrap 12 from tipping or shifting during conveyance by the conveyor, thereby improving identification accuracy. On the other hand, if the approximately T-shaped molding scrap 12 is tilted sideways, i.e., so that the tip of the axial sprue portion 7 contacts the belt conveyor, the molding scrap 12 may tip or shift during transport on the belt conveyor, resulting in reduced identification accuracy. When separating and collecting molding scrap of various shapes, it is preferable to arrange the molding scrap on the conveyor so that the convex or acute-angled portion faces upward. In some embodiments, if the vibration transport process is included, the molding scrap are arranged on the conveyor with their shapes aligned after the vibration transport process. This arrangement on the conveyor with aligned orientation is performed, for example, by an arm-type robot or a picking robot.

[0139] The intervals between the molding waste products on the conveyor are preferably 1 to 30 cm, more preferably 1 to 20 cm, and even more preferably 1 to 10 cm in the conveyor travel direction from the viewpoint of preventing erroneous recognition. The intervals between the molding waste products on the conveyor are preferably 1 to 30 cm, more preferably 1 to 20 cm, and even more preferably 1 to 10 cm in the conveyor width direction (direction perpendicular to the conveyor travel direction) from the viewpoint of reducing and preventing erroneous recognition.

[0140] The speed at which the molding waste products are fed to the conveyor is not particularly limited, but from the viewpoint of reducing or preventing erroneous recognition, it is preferably 0.5 to 5 products / second, more preferably 0.5 to 4 products / second, and even more preferably 1 to 3 products / second.

[0141] The speed of the conveyor is not particularly limited, but is preferably 10 to 100 m / sec, more preferably 20 to 80 m / sec, and even more preferably 30 to 50 m / sec.

[0142] The speed of the sorting and recovery process for the molding waste is not particularly limited, but is preferably 0.2 to 3.0 pieces / second, and more preferably 0.3 to 2.0 pieces / second. The "sorting and recovery process speed" refers to the processing speed from when the laser light is irradiated onto the molding waste to when the type of thermoplastic resin in the molding waste is identified and the waste is sorted and recovered.

[0143] Of course, the separation and recovery step may be carried out discontinuously.

[0144] (Identification) In an embodiment of the present invention, in the separation and recovery process, Raman scattering spectra are used to identify the thermoplastic resins that make up the molding waste. Laser light is irradiated onto the molding waste, and the type of thermoplastic resin that makes up the molding waste is identified based on the Raman scattered light scattered from the molding waste. Resin identification using Raman scattered light can distinguish between resins that have different structural units of the thermoplastic resin that makes up the molding waste. Using this identification method based on Raman scattered light makes it possible to separate and recover different types of thermoplastic resins with high identification accuracy, thereby improving recycling efficiency and / or the quality of the recycled resin.

[0145] Identification of the type of resin using Raman scattered light can be carried out, for example, by using a Raman scattering identification device 13, as shown in Fig. 4. The Raman scattering identification device 13 irradiates the molding waste 12 with laser light (not shown), and identifies the type of thermoplastic resin in the molding waste based on the Raman scattered light scattered from the molding waste.

[0146] The Raman scattering identification device typically includes a means for irradiating laser light, measuring the Raman scattering spectrum, and acquiring Raman scattering information, and an identification means for analyzing the measured Raman scattering information and known Raman scattering information (Raman scattering information of a reference resin) to identify the type of resin constituting the molding waste. For example, first, Raman scattering information of the known resin to be identified (Raman scattering information of the reference resin) is acquired. Next, laser light is irradiated onto the molding waste, which is the resin to be identified, to measure the Raman scattering spectrum and acquire the Raman scattering information of each resin. The Raman scattering information of the reference resin is then compared with the measured Raman scattering information of the resin to be identified to identify the type of resin. Figure 4 shows a top view of the Raman scattering identification device 13. As shown in Figure 4, the Raman scattering identification device 13 includes a laser light irradiation unit (not shown) located above the belt conveyor 16 and a sensor 17 located above the belt conveyor 16. Laser light is irradiated from the laser light irradiating unit onto the molding waste products (12a, 12b) on the belt conveyor 16, and the reflected Raman light is captured by a sensor 17, thereby measuring the Raman scattering spectrum and acquiring Raman scattering information. The Raman scattering information is processed by an analyzer (not shown) provided in the Raman scattering identification device 13, and the type of resin is identified. Such Raman scattering identification devices are described, for example, in Japanese Patent No. 4203916, JP 2009-092458 A, JP 2011-214917 A, and JP 2012-42248 A, and these devices can also be preferably used in the manufacturing method of this embodiment.

[0147] In the manufacturing method of this embodiment, as described above, the thermoplastic resin contains at least one selected from the structural unit (A) derived from a monomer represented by general formula (1), the structural unit (B) derived from a monomer represented by general formula (2), the structural unit (C) derived from a monomer represented by general formula (3), the structural unit (D) derived from a monomer represented by general formula (4), and the structural unit (E) derived from a monomer represented by general formula (5). By using an identification method based on Raman scattered light to recognize and identify differences in the intensity and pattern of scattered light, it becomes possible to accurately and quickly identify thermoplastic resins containing at least one selected from the structural unit (A), the structural unit (B), the structural unit (C), the structural unit (D), and the structural unit (E), which differ in the type of structural unit of the resin, the ratio of multiple structural units when multiple structural units are included, and the like.

[0148] (Separate Collection) After the type of thermoplastic resin in the molding waste is identified as described above, the molding waste is separated and collected according to the type of thermoplastic resin that constitutes the molding waste, depending on the identification results. If the type of thermoplastic resin in the molding waste matches the resin to be collected, it is collected as molding waste to be collected. On the other hand, if the type of thermoplastic resin in the molding waste matches the resin to be collected, it is excluded from the molding waste to be collected and, if necessary, collected as molding waste not to be collected. In some embodiments, the separate collection step includes collecting molding waste to be collected by spraying compressed air, and / or removing molding waste not to be collected by spraying compressed air.

[0149] For example, as shown in FIG. 4 , the Raman scattering identification device has a mechanism (means) for ejecting compressed air 14 in response to the identification result based on the Raman scattered light. In the separate collection, if the type of thermoplastic resin constituting the molding waste matches the resin to be collected based on the Raman scattered light, the molding waste is ejected with compressed air 14 and collected as the molding waste 12a to be collected in a collection container 15 installed outside the Raman scattering identification device 13. Although not shown, multiple molding waste products may be collected based on the identification result based on the Raman scattered light. For example, by ejecting compressed air 14 in response to the identification result based on the Raman scattered light, the first type of molding waste 12a (identified product) to be collected may be collected in the collection container 15, and then, on the downstream side of the belt conveyor, the second type of molding waste 12a (identified product) to be collected may be collected in the collection container 15, and further downstream, the third and subsequent types of molding waste 12a (identified product) to be collected may be sequentially collected.

[0150] 5 is a schematic diagram illustrating a method for separating and collecting molding waste in a separation and collection step according to another embodiment of the present invention. In the embodiment shown in FIG. 5, if the type of thermoplastic resin constituting the molding waste does not match the resin to be collected according to the identification result based on Raman scattered light, the molding waste is ejected with compressed air 14 and discharged outside the belt conveyor 16 (outside the Raman scattering identification device 13) as molding waste 12b (non-identifiable product) that is not to be collected, and molding waste 12a (identifiable product) that is to be collected is collected downstream of the belt conveyor 16. The collection mechanism shown in FIG. 4 and the collection mechanism shown in FIG. 5 may be combined to separate and collect the molding waste 12a to be collected and the molding waste 12b (non-identifiable product) that is not to be collected.

[0151] In Figures 4 and 5, compressed air 14 is used to collect the molded waste products 12a that are to be collected and the molded waste products 12b that are not to be collected (non-identifiable products). However, instead of compressed air 14, an inert gas may be sprayed to separately collect the molded waste products 12a that are to be collected and the molded waste products 12b that are not to be collected (non-identifiable products).

[0152] 3. Recycled Resin Manufacturing Process The recycled resin manufacturing process is a process for obtaining recycled resin from the separated and collected molding waste. Since the molding waste is obtained from the separated and collected process, it contains the same type of thermoplastic resin. Therefore, in the recycled resin manufacturing process, it is possible to produce high-quality recycled resin from the molding waste with high recycling efficiency.

[0153] The recycled resin manufacturing process is not particularly limited as long as it can obtain recycled resin from the separated and collected molding waste, and any known method can be used. In a preferred embodiment, the recycled resin manufacturing process includes a process of pulverizing the molding waste (pulverization process), a process of removing impurities contained in the molding waste (impurity removal process), and a process of manufacturing recycled resin (resin manufacturing process).

[0154] (Crushing Step) The crushing step is a step of crushing the molding waste.

[0155] The molding waste can be crushed into a shape suitable for recycling.

[0156] The pulverization method is not particularly limited, and any of compression, impact, shear, and friction methods may be used.

[0157] Examples of crushers that can be used include coarse crushers such as jaw crushers, gyratory crushers, impact crushers, uniaxial crushers, and biaxial 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, vibration ball mills, rod mills, jet mills, and planetary mills. Of these, coarse crushers are preferred, and uniaxial crushers and biaxial crushers are more preferred. Specific examples of crushers include high-power crushers 35-560, 35-720, 55-770, and 55-1050 (manufactured by Tanaka Corporation), and low-speed crushers KGA-250 and KGA-350 (manufactured by Kawata Corporation). The above-mentioned crushers may be used alone or in combination of two or more.

[0158] (Impurity Removal Step) The impurity removal step is a step of removing impurities contained in the molding waste. The molding waste may contain two or more types of resin. The molding waste may also contain additives, decomposition products of resins, decomposition products of additives, etc. From the viewpoint of producing a recycled resin with excellent physical properties, it is preferable to remove impurities from the molding waste.

[0159] The method for removing impurities contained in molding waste products is not particularly limited, and examples thereof include a method that utilizes the difference in physical properties between the target resin and the impurities, and a method that utilizes the difference in chemical properties between the target resin and the impurities.

[0160] Methods that utilize the difference in physical properties between the target resin and impurities include a method that uses magnetic force, a method that uses wind force, a method that uses a sieve, a method that uses specific gravity, and a method that uses buoyancy.

[0161] For example, if the impurities are metals, they can be removed by a method using magnetic force. Specifically, metals that may be contained in the waste composition can be removed by using a magnet or a metal detector. Other methods that can be applied include a method of removing impurities using salt water to utilize differences in buoyancy, a method of removing impurities using activated carbon to utilize differences in adsorption force, and a method of removing impurities using hydrocyclone treatment to utilize differences in specific gravity.

[0162] As a method utilizing the difference in chemical properties between the target resin and impurities, there is a method of depolymerizing the target resin.

[0163] For example, a resin having at least one structural unit selected from the group consisting of the structural unit (A), the structural unit (B), the structural unit (C), the structural unit (D), and the structural unit (E) can be depolymerized by treating it with an alkaline aqueous solution to obtain at least one monomer compound (depolymerized monomer) selected from the group consisting of the general formulae (1) to (5).

[0164] When molding waste contains, in addition to a thermoplastic resin having at least one structural unit selected from the group consisting of the structural units (A) to (E), other resins that are not depolymerized (for example, impurity resins such as cyclic polyolefins), treatment with an alkaline aqueous solution results in depolymerization of only the resin having at least one structural unit selected from the group consisting of the structural units (A) to (E). The resulting monomer compound (depolymerized monomer) has properties that are significantly different from those of the other resins that are not depolymerized (impurity resins), and therefore the other resins that are not depolymerized (impurity resins) can be removed.

[0165] The alkali treatment can be carried out by any known method without any particular limitation. For example, the alkali treatment can be carried out by adding the waste composition and an alkaline aqueous solution to a reaction solvent and allowing them to react with each other.

[0166] The reaction solvent is not particularly limited, but examples thereof include aliphatic hydrocarbon solvents and aromatic hydrocarbon solvents.

[0167] The aliphatic hydrocarbon solvent is not particularly limited, but examples thereof include pentane, hexane, heptane, octane, nonane, decane, cyclohexane, and cyclodecane.

[0168] The aromatic hydrocarbon solvent is not particularly limited, but examples thereof include toluene, xylene, and mesityle.

[0169] Among these, the reaction solvent is preferably an aromatic hydrocarbon solvent, more preferably toluene or xylene. The above-mentioned reaction solvents may be used alone or in combination of two or more.

[0170] The amount of reaction solvent used is not particularly limited, but is preferably 30 to 2000 parts by mass, more preferably 40 to 1500 parts by mass, and even more preferably 100 to 1000 parts by mass, relative to 100 parts by mass of the waste composition. When the amount of reaction solvent used is 30 parts by mass or more, the organic components of the waste composition are sufficiently dissolved in the reaction solvent, which is preferable, thereby increasing the reaction efficiency. On the other hand, when the amount of reaction solvent used is 2000 parts by mass or less, the reaction time is shortened, which is preferable.

[0171] In some embodiments, the alkaline aqueous solution comprises a metal hydroxide and water.

[0172] The metal hydroxide is not particularly limited, but examples thereof include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and rubidium hydroxide; and alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide. Among these, the metal hydroxide is preferably an alkali metal hydroxide, more preferably sodium hydroxide or potassium hydroxide, and even more preferably potassium hydroxide. These metal hydroxides may be used alone or in combination of two or more.

[0173] The amount of the metal hydroxide used is not particularly limited, but is preferably 1.5 to 10 mol, more preferably 2 to 8 mol, and even more preferably 2 to 4 mol, per mol of carbonate bond in the polycarbonate resin. When the amount of the metal hydroxide used is 1.5 mol or more, depolymerization is carried out sufficiently, which is preferable. On the other hand, when the amount of the metal hydroxide used is 10 mol or less, production costs are reduced, which is preferable.

[0174] The concentration of the metal hydroxide in the alkaline aqueous solution is preferably 10 to 60% by mass, more preferably 15 to 55% by mass, and even more preferably 20 to 50% by mass, based on the total mass of the alkaline aqueous solution. A metal hydroxide concentration of 10% by mass or more is preferred because it increases the depolymerization reaction rate. On the other hand, a metal hydroxide concentration of 60% by mass or less is preferred because it prevents the alkaline aqueous solution from becoming a slurry and facilitates the reaction to proceed.

[0175] The treatment temperature (depolymerization reaction temperature) is not particularly limited, but is preferably 120° C. or lower, more preferably 100° C. or lower, and even more preferably 30 to 90° C. A treatment temperature of 120° C. or lower is preferred because side reactions can be prevented.

[0176] <Resin Manufacturing Process> The resin manufacturing process is a process for manufacturing recycled resin.

[0177] In the impurity removal process, if the impurities are removed by a method that utilizes the difference in physical properties between the target resin and the impurities, the structure of the target resin remains unchanged, and the resin obtained by removing the impurities becomes a recycled resin.

[0178] On the other hand, when the impurities are removed by a method that utilizes the difference in chemical properties between the target resin and the impurities, a recycled resin can be produced by polymerizing the depolymerized monomer of the target resin. In this case, the recycled resin produced may be the same as or different from the target resin contained in the molding waste.

[0179] The method for polymerizing the depolymerized monomer of the target resin to produce the recycled resin is not particularly limited, and can be produced by any known method. For example, when the depolymerized monomer is at least one monomer compound selected from the group consisting of the general formulas (1) to (4), a polycarbonate resin can be produced as the recycled resin by subjecting a dihydroxy compound (diol) represented by formula (1), formula (2), and / or formula (4) and a carbonate diester to a solution condensation method in the presence of a basic compound catalyst and / or a transesterification catalyst, or in the absence of a catalyst. Furthermore, a polyestercarbonate resin can be produced as the recycled resin by subjecting a dihydroxy compound (diol) represented by formula (1), formula (2), and / or formula (4), a monomer compound represented by formula (3), and a carbonate diester to a solution condensation method in the presence of a basic compound catalyst and / or a transesterification catalyst, or in the absence of a catalyst. Furthermore, a polyester resin can be produced as a recycled resin by reacting a dihydroxy compound (diol) represented by formula (1), formula (2), and / or formula (4) with a dicarboxylic acid (ester) compound in the presence of a basic compound catalyst and / or a transesterification catalyst. Alternatively, a polyester resin can be produced as a recycled resin by reacting a dihydroxy compound with a dicarboxylic acid (ester) compound represented by formula (3) in the presence of a basic compound catalyst and / or a transesterification catalyst. Alternatively, a polyester resin can be produced as a recycled resin by reacting a dihydroxy compound with a dicarboxylic acid (ester) compound represented by formula (5) in the presence of a basic compound catalyst and / or a transesterification catalyst. In the above processes, compounds that derive structural units of other polycarbonate resins, compounds that derive structural units of other resins (polyester resins, polyestercarbonate resins, polyolefin resins), etc. can be used in combination with the compounds that derive structural units represented by formulas (1) to (5) and the carbonate diesters.

[0180] The carbonic acid diester is not particularly limited, but examples thereof include diphenyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, etc. Among these, diphenyl carbonate is preferred.

[0181] The amount of the diester carbonate compound used is preferably 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, and even more preferably 1.00 to 1.10 mol, per mol of the dihydroxy compound.

[0182] The basic compound catalyst is not particularly limited, but examples thereof include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.

[0183] The alkali metal compound is not particularly limited, and examples thereof include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkali metals.Specific examples thereof include 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 phenylphosphate, disodium salt, dipotassium salt, dicesium salt, or dilithium salt of bisphenol A, and sodium salt, potassium salt, cesium salt, or lithium salt of phenol.

[0184] The alkaline earth metal compound is not particularly limited, and examples thereof include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkaline earth metal compounds. Specific examples include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, and magnesium phenylphosphate.

[0185] The nitrogen-containing compound is not particularly limited, but examples thereof include quaternary ammonium hydroxides, salts thereof, amines, etc. Specific examples include quaternary ammonium hydroxides having an alkyl group, an aryl group, etc., such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide; tertiary amines such as triethylamine, dimethylbenzylamine, and triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as propylamine and butylamine; imidazoles such as 2-methylimidazole, 2-phenylimidazole, and benzimidazole; ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, and tetraphenylammonium tetraphenylborate.

[0186] Examples of the transesterification catalyst include salts of zinc, tin, zirconium, lead, etc. Specific examples include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin(II) chloride, tin(IV) chloride, tin(II) acetate, tin(IV) acetate, dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead(II) acetate, and lead(IV) acetate.

[0187] The above-mentioned basic compound catalysts and transesterification catalysts may be used alone or in combination of two or more kinds.

[0188] The amount of the basic compound catalyst and the transesterification catalyst (total amount when used in combination) used is 1 × 10 per mole of the dihydroxy compound. －９ ~1 x 10 －３ mol, preferably 1×10 －７ ~1 x 10 －４ More preferably, it is moles.

[0189] In the melt polycondensation method, it is desirable to melt a dihydroxy compound, a dicarboxylic acid (ester) compound, and a carbonate diester in a reaction vessel, and then carry out the reaction while retaining the produced monohydroxy compound. In order to retain the monohydroxy compound, the pressure can be controlled by, for example, blocking the reaction vessel or reducing or increasing the pressure.

[0190] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these. Unless otherwise specified, "%" is by weight.

[0191] The Raman scattering device used was a device manufactured by Cyme Co., Ltd. The weight average molecular weight (Mw) was calculated from the GPC retention time based on a calibration curve prepared using a gel permeation chromatograph (GPC) with tetrahydrofuran as a developing solvent and standard polystyrene of known molecular weight (molecular weight distribution = 1).

[0192] The molded bodies PC1, PC2, PC3, PC4, PC5, PC6 and PC7 used as molding waste are as follows.

[0193] BNEF: 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene BNE: 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene BPEF: 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene BPPEF: 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene BPA: Bisphenol A D-NDM: Decahydro-1,4:5,8-dimethanonaphthalenediol

[0194] (1) PC1:BNEF / BNE / BPPEF BNEF / BNE / BPPEF = x / y / x = 27.0 / 52.0 / 21.0 (mol%) Mw = 33,000 Synthesized by the method described in International Publication WO2018 / 016516.

[0195] (2) PC2: BNE / BPPEF BNE / BPPEF = x / y = 45.0 / 55.0 (mol%) Mw = 47,000 Synthesized by the method described in International Publication WO2014 / 073496.

[0196] (3) PC3: BNE / BPEF BNE / BPEF = x / y = 42.1 / 57.9 (mol%) Mw = 35,000 Synthesized by the method described in International Publication WO2014 / 073496.

[0197] (4) PC4:BPEF-HOMO Mw = 29,000. Synthesized according to the method described in Synthesis Example 2 of International Publication WO2015 / 166951.

[0198] (5) PC5: BPEF / BPA BPEF / BPA = x / y = 65.8 / 34.2 (mol %) Mw = 30,000 Synthesized by the method described in International Publication WO2007 / 142149.

[0199] (6) PC6: BPEF / BPA BPEF / BPA = x / y = 13.6 / 86.4 (mol %) Mw = 31,000 Synthesized by the method described in International Publication WO2007 / 142149.

[0200] (7) PC7: D-NDM / BPEF D-NDM / BPEF = x / y = 66 / 34 (mol%) Mw = 28,000 Synthesized by the method described in International Publication WO2016 / 052370.

[0201] [Example 1-1] (1) Vibration Transport Process Molding waste collected from an optical material manufacturing plant was used. Specifically, molding waste including a sprue and runner portion discharged after molding optical lenses from each of the resins PC1, PC2, PC3, PC4, PC5, PC6, and PC7 was used. Each molding waste had a structure in which a plastic product 11 was separated from a single unit shown in FIG. 3 . Each molding waste had a shaft-shaped sprue portion 7 (inner diameter: 4.3 mm, length: 48.1 mm), eight leg-shaped (branched) runner portions 8 (inner diameter: 2.5 mm, length to the branched portion: 12 mm, length of each branched portion: 9.6 mm) extending evenly circumferentially from below the shaft, a gate portion 9 (inner diameter: 1.0 mm), and a cold slug well portion 10 (inner diameter: 4.3 mm, length: 6.3 mm) at the end of the sprue portion. The molding waste was fed into one end of a conveyor (vibrating conveying bed, width: 30 cm, length: 1.5 m) vibrating at 50 Hz. 500 g of molding waste was fed over 10 seconds. After the molding waste reached the other end of the vibrating conveying bed, the molding waste was collected. This process eliminated entanglement between the molding waste, and the untangled molding waste could be efficiently arranged one by one on the conveyor of the Raman scattering device for the subsequent sorting and collection process.

[0202] (2) Separation and Recovery Process: Using the Raman scattering device shown in FIG. 4, the resin type to be identified was designated PC1, and the identified resin type was set to be blown with air. The belt conveyor speed of the device was set to 20 m / min. Ten pieces of each molding waste were randomly and evenly spaced and placed on the aforementioned belt conveyor at a rate of one piece per second. When placed on the belt conveyor, as shown in FIG. 6B, each molding waste was arranged in an inverted T-shape, with the shaft of the sprue portion 7 extending upward and the eight leg-like runner portions 8 extending evenly circumferentially from below the shaft in contact with the belt conveyor. As a result, all moldings were 100% sorted. The operating conditions and results are shown in Table 1.

[0203] Examples 1-2 to 1-7 were carried out in the same manner as in Example 1-1, except that the operating conditions of the apparatus were changed as shown in Table 1. As a result, all molded bodies were 100% selected. The operating conditions and results are shown in Table 1.

[0204] [Example 1-8] The same procedure as in Example 1-1 was carried out, except that five of the ten molding waste products were placed on their sides on the belt conveyor so that the tip of the sprue portion 7 was in contact with the belt conveyor. The operating conditions and results are shown in Table 1. As a result, the success rate of identification was 50%. The operating conditions and results are also shown in Table 1.

[0205] Examples 2-1 to 6-1 The same procedures as in Example 1-1 were carried out except that the types of resins used for identification were as shown in Table 2. Table 2 shows the operating conditions and results.

[0206] Example 7-1: A Raman scattering device of the embodiment shown in Figure 5 was used, with the resin type to be identified and set to PC1, and resin types other than the identified type being blown with air. The speed of the conveyor belt of the device was set to 20 m / min. The molded articles used were sprues and runners discharged after molding optical lenses from each of the resins PC1, PC2, PC3, PC4, PC5, PC6, and PC7. As in Example 1-1, each molding waste product had a structure in which a plastic product 11 was separated from the integrated product shown in Figure 3. Each molding waste product had a shaft-shaped sprue portion 7 (inner diameter: 4.3 mm, length: 48.1 mm), eight leg-shaped (branched structure) runner portions 8 (inner diameter: 2.5 mm, length to the branched structure: 12 mm, length of each branched structure portion: 9.6 mm) extending evenly from below the shaft in the circumferential direction, a gate portion 9 (inner diameter: 1.0 mm), and a cold slug well portion 10 (inner diameter: 4.3 mm, length: 6.3 mm) at the end of the sprue portion. Prior to the separation and recovery process using the Raman scattering light device, a vibration transport process was carried out in the same manner as in Example 1-1 to disentangle the molding waste products from each other. Ten molding waste products of each type were randomly and equidistantly placed on the aforementioned belt conveyor at a speed of 1 piece per second. When placing the molding waste on the belt conveyor, as shown in Figure 6B, the orientation of each molding waste was aligned in an inverted T shape so that the shaft of the sprue portion 7 extended upward and the eight leg-like runner portions 8 extending evenly circumferentially from below the shaft were in contact with the belt conveyor. As a result, all moldings were 100% sorted. The operating conditions and results are shown in Table 3.

[0207] Examples 7-2 to 7-6 were carried out in the same manner as in Example 7-1, except that the operating conditions of the apparatus were changed as shown in Table 3. As a result, all molded bodies were 100% selected. The operating conditions and results are shown in Table 3.

[0208] [Examples 8-1 to 12-1] The same procedure as in Example 7-1 was carried out, except that the identification resin types were as shown in Table 4. As a result, all molded bodies were 100% selected. The operating conditions and results are shown in Table 4.

[0209] Example 13 Using the PC-4 (polycarbonate resin containing structural units derived from 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF)) recovered in Example 1-1, after pulverization, a recycled resin was produced in the same manner as in Synthesis Example 2 of WO 2015 / 166951. Specifically, the recycled resin was produced by the following procedure. A reactor equipped with a stirrer and a cooling tube was charged with 100 parts by weight of the pulverized PC4, 88 parts by weight of a 48% aqueous sodium hydroxide solution, and 734 parts by weight of toluene, and the mixture was reacted under reflux for 3 hours. The liquid temperature was then cooled to 80-85°C, and 178 parts by weight of ion-exchanged water was added. After stirring and allowing to stand, the aqueous phase was separated, and the organic phase was washed with ion-exchanged water. The toluene was partially distilled off from the organic phase, followed by filtration, 23 parts of ion-exchanged water was added, and the mixture was cooled to room temperature with stirring. The precipitated crystals were filtered and dried to obtain 85 parts by weight of white crystals of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF). Subsequently, 19.5 kg (44.5 mol) of the 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) obtained above, 9.81 kg (45.8 mol) of diphenyl carbonate, and 2.2 × 10 sodium bicarbonate were added. －２ g (2.7 x 10 －４ (mol) was placed in a 50-liter reactor equipped with a stirrer and distillation device, and heated to 215°C over 1 hour under a nitrogen atmosphere of 760 mmHg with stirring. The degree of vacuum was then adjusted to 150 mmHg over 15 minutes, and the mixture was maintained at 215°C and 15 mmHg for 20 minutes to carry out a transesterification reaction. The temperature was then raised to 240°C at a rate of 37.5°C / hr and maintained at 240°C and 150 mmHg for 10 minutes. The pressure was then adjusted to 120 mmHg over 10 minutes and maintained at 240°C and 120 mmHg for 70 minutes. The pressure was then adjusted to 100 mmHg over 10 minutes and maintained at 240°C and 100 mmHg for 10 minutes. The pressure was then reduced to 1 mmHg or less over 40 minutes, and the polymerization reaction was carried out under stirring for 10 minutes under conditions of 240°C and 1 mmHg or less. After the reaction was completed, nitrogen was blown into the reactor to increase the pressure, and the polycarbonate resin produced was pelletized and discharged. The polycarbonate resin obtained had a Mw of 28,000.

[0210] As described above, BPEF obtained from the separated and recovered resin was reacted with a carbonate diester by the solution condensation method, thereby producing a recycled resin containing the structural unit of BPEF.

[0211]

[0212]

[0213]

[0214]

[0215] The results in Tables 1 to 4 confirm that the use of Raman scattering light allows the type of thermoplastic resin in molding waste to be identified and efficiently separated and recovered. When the axial sprue sections were aligned so that their tips faced upward, the identification rate of the type of thermoplastic resin was higher (100%) and the accuracy of separation and recovery was improved compared to Examples 1-8, in which the axial sprue sections were arranged so that their tips were in contact with the belt conveyor. It was also shown that the recycled resin produced from the separated and recovered molding waste had sufficient molecular weight and could be used to produce high-quality resin (Example 13).

[0216] REFERENCE SIGNS LIST 1 Mold 2 Sprue 3 Runner 4 Gate 5 Cavity core 6, 6' Cold slug well 7 Sprue section 8 Runner section 9 Gate section 10, 10' Cold slug well section 11 Plastic product 12 Molding waste 12a Molding waste to be collected 12b Molding waste not to be collected 13 Raman scattering identification device 14 Compressed air 15 Collection container 16 Belt conveyor 17 Sensor

Claims

1. A method for manufacturing recycled resin, A process of irradiating molded waste made of thermoplastic resin with laser light, identifying the type of thermoplastic resin in the molded waste based on the Raman scattered light scattered from the molded waste, and separating and recovering it; A step of obtaining recycled resin from the molded waste that has been separated and collected, Includes, A method for producing the thermoplastic resin, comprising at least one selected from the 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). 【Transformation 38】 [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 This 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. X represents a fluorene group that is either a single bond or may have substituents. A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have substituents. m and n each independently represent integers from 0 to 6. a and b each independently represent integers between 0 and 10. 【Chemistry 39】 [In formula (2), R ｃ and R ｄ Each of these is independently selected from the group consisting of 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, and an optionally substituted C6-C20 aryl group. 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 of these 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. Ph represents a phenyl group, r and s each independently represent integers between 0 and 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 integers from 0 to 4. a and b each independently represent integers between 0 and 10. 【Chemistry 40】 [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 This 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. X represents a fluorene group that is either a single bond or may have substituents. A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have substituents. m and n each independently represent integers from 0 to 6. a and b each independently represent integers from 0 to 10. R' and R'' are each independently selected from the group consisting of a hydroxyl group, a halogen atom, an optionally substituted alkoxy group having 1 to 20 carbon atoms, and an optionally substituted aryloxy group having 6 to 20 carbon atoms. 【Chemistry 41】 [In formula (4), R ｇ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 【Chemistry 42】 [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. K １ and K ２ Each of these independently represents a hydroxyl group, an alkoxy group, or a halogen atom. 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 of these independently represents a phenyl group or a naphthyl group, which may have substituents. r １ and r ２ Each of these independently represents an integer between 0 and 2. r ３ and r ４ Each of these independently represents an integer between 0 and 1.

2. The manufacturing method according to claim 1, wherein the thermoplastic resin comprises at least one selected from monomer-derived constituent units (A) represented by general formula (1), monomer-derived constituent unit (B) represented by general formula (2), monomer-derived constituent unit (C) represented by general formula (3), and monomer-derived constituent unit (D) represented by general formula (4).

3. The manufacturing method according to claim 2, wherein the thermoplastic resin 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).

4. The manufacturing method according to claim 2, wherein the thermoplastic resin is represented by any of the following formulas (I-1), (I-2), (I-3), (II-1), (II-2), (II-3), (II-4), (II-5), or (II-6). 【Chemistry 43】 【change】 [In the formula, x, y, and z represent the number of repeating units.]

5. The aforementioned thermoplastic resin (III-1) A resin containing the constituent units represented by the following formula (iii-a1), formula (iii-a2), formula (iii-a3), and formula (iii-a4); (III-2) A resin containing the constituent units represented by the following formula (iii-a1), formula (iii-a2), formula (iii-a4), and formula (iii-a5); (III-3) A resin containing a constituent unit represented by the following formula (iii-a1), a constituent unit represented by the formula (iii-a4), and a constituent unit represented by the formula (iii-a6); A manufacturing method according to claim 1, selected from the group consisting of the following. 【Chemistry 44】

6. The manufacturing method according to claim 1, wherein the molding waste comprises a sprue portion and / or a runner portion that is discharged after molding an optical material.

7. The manufacturing method according to any one of claims 1 to 6, wherein the sorting and collection process is performed continuously on a conveyor, and the supply speed of the molded waste to the conveyor is 0.5 to 5 pieces / second.

8. The aforementioned process of sorting and collecting materials is: Collecting molded waste to be recovered by spraying compressed air, and / or By spraying compressed air, non-recoverable molded waste is removed. The manufacturing method according to claim 1, including

9. The manufacturing method according to claim 1, further comprising the step of supplying the waste composition, including the molded waste, to a vibrating transport bed and vibrating the waste composition before the aforementioned sorting and collection step.

10. The manufacturing method according to claim 9, further comprising the step of supplying molded waste products onto a conveyor at equal intervals in the aforementioned sorting and collection step.

11. The aforementioned molded waste product comprises an axial sprue portion and two or more runner portions extending evenly in the circumferential direction from below the axial portion. The manufacturing method according to claim 10, wherein the molded waste is arranged so that the tip of the axial sprue portion faces upward.

12. A method for sorting and collecting molded waste, The process includes irradiating molded waste made of thermoplastic resin with laser light, identifying the type of thermoplastic resin in the molded waste based on the Raman scattered light scattered from the molded waste, and then separating and recovering the materials. A method for sorting and recovering a thermoplastic resin, wherein the thermoplastic resin comprises at least one selected from monomer-derived constituent units (A) represented by the following general formula (1), monomer-derived constituent units (B) represented by the following general formula (2), monomer-derived constituent units (C) represented by the following general formula (3), monomer-derived constituent units (D) represented by the following general formula (4), and monomer-derived constituent units (E) represented by the following general formula (5). 【Chemistry 45】 [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 This 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. X represents a fluorene group that is either a single bond or may have substituents. A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have substituents. m and n each independently represent integers from 0 to 6. a and b each independently represent integers between 0 and 10. 【Chemistry 46】 [In formula (2), R ｃ and R ｄ Each of these is independently selected from the group consisting of 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, and an optionally substituted C6-C20 aryl group. Y is a single bond, a fluorene group which may have substituents, -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 - Selected from the group consisting of, R ２１ , R ２２ , R ２３ , R ２４ , R ２５ and R ２６ Each of these 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. Ph represents a phenyl group, r and s each independently represent integers between 0 and 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 integers from 0 to 4. a and b each independently represent integers between 0 and 10. 【Chemistry 47】 [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 This 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. X represents a fluorene group that is either a single bond or may have substituents. A and B each independently represent an alkylene group having 1 to 5 carbon atoms, which may have substituents. m and n each independently represent integers from 0 to 6. a and b each independently represent integers from 0 to 10. R' and R'' are each independently selected from the group consisting of a hydroxyl group, a halogen atom, an optionally substituted alkoxy group having 1 to 20 carbon atoms, and an optionally substituted aryloxy group having 6 to 20 carbon atoms. 【Chemistry 48】 [In formula (4), R ｇ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 【Chemistry 49】 [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. K １ and K ２ Each of these independently represents a hydroxyl group, an alkoxy group, or a halogen atom. 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 of these independently represents a phenyl group or a naphthyl group, which may have substituents. r １ and r ２ each independently represents an integer from 0 to 2, r ３ and r ４ Each of these independently represents an integer between 0 and 1.

13. The separation and recovery method according to claim 12, wherein the thermoplastic resin comprises at least one selected from monomer-derived constituent units (A) represented by general formula (1), monomer-derived constituent units (B) represented by general formula (2), monomer-derived constituent units (C) represented by general formula (3), and monomer-derived constituent units (D) represented by general formula (4).

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