Method of producing thermoplastic resin

Abstract

Provided is a method for producing a recycled resin from a waste resin composition, wherein the waste resin composition comprises: a thermoplastic resin B which contains one or more thermoplastic resins that are selected from the group consisting of a thermoplastic resin B1 that contains a constituent unit (b-1) which is derived from a monomer represented by general formula (1-1), a thermoplastic resin B2 that contains a constituent unit (b-2) which is derived from a monomer represented by general formula (1-2), and a thermoplastic resin B3 that contains a constituent unit (b-3) which is derived from a monomer represented by general formula (1-3); and at least one of a thermoplastic resin C which contains only a constituent unit (c) that is derived from a monomer represented by general formula (2), and a thermoplastic resin D which contains at least one constituent unit that is selected from the group consisting of general formulae (7) to (10). This method comprises: pulverizing the waste resin composition so as to obtain a pulverized material; and sorting out the thermoplastic resin B, and the thermoplastic resin C and the thermoplastic resin D by means of UV.

Description

Thermoplastic resin manufacturing method

[0001] The present invention relates to a method for producing a thermoplastic resin. More particularly, the present invention relates to a method for producing a thermoplastic resin, which includes producing a recycled resin from a waste resin composition.

[0002] Thermoplastic resins are one of the most useful resins used in various fields in daily life, and recycling such thermoplastic resins has attracted considerable interest. However, the spools and runners discarded after molding in the manufacturing process of thermoplastic resin products are not always effectively utilized. One reason for this is that spools and runners collected as waste resin materials are first crushed and used to produce recycled resin. However, the crushed materials may contain trace amounts of other grades or resins, making it necessary to separate and recover these resins. Patent Document 1 describes optical sorting of plastics by resin type (Patent Document 1: Figure 8). However, it has been difficult to obtain high-purity recycled resin by further separating the same type of resin. Furthermore, methods for producing recycled resin from waste resin compositions have been developed, including a process involving contact with salt water, a process involving contact with activated carbon, a process involving hydrocyclone treatment, and a process involving depolymerizing the resin to form monomers and then repolymerizing them, but there is room for improvement (Patent Document 2). Furthermore, in particular for optical material applications, the optical properties are more likely to be affected by the inclusion of unintended resin species than in other resin applications, and therefore recycled resins are required to have the same level of purity as new resins. Therefore, there remains a need for a method for obtaining high-purity recycled resins, particularly from waste resin compositions containing multiple resins of the same type.

[0003] Patent Publication No. 2010-167727 WO 2021 / 200892

[0004] The present invention provides a method for producing recycled resin from a waste resin composition.

[0005] The present invention includes the following aspects: <1> A method for producing recycled resin from a waste resin composition, wherein the waste resin composition comprises: a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the following general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the following general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and at least one of a thermoplastic resin C containing only a structural unit (c) derived from a monomer represented by the following general formula (2), and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the following general formulas (7) to (10), wherein the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and sorting the thermoplastic resin B, the thermoplastic resin C, and the thermoplastic resin D using UV light. [In general formula (1-1), R ａ and R ｂ are each independently a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ is selected from 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; m and n each independently represent an integer of 0 to 5; X represents a single bond, —O—, —S—, —SO—, —SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of the groups is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. [In general formula (1-2), R ａ and Rｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, preferably an integer of 0 to 3; a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3; R' and R'' each independently represent a 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 general formula (1-3), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent.] [In general formula (2), R ｃ and R ｄare each independently a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ is selected from 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; p and q each independently represent an integer of 0 to 5; Y １ represents a single bond, —O—, —S—, —SO—, —SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of the groups is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. [In general formulas (7) to (10), X ｇ each independently represents an alkylene group having 1 to 10 carbon atoms; ｊ , R ｋ , and R ｌ each independently represents a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, and —C≡C—R ｉ is selected from R ｉrepresents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S; each p independently represents an integer of 0 or 1; each q, r, and s independently represents an integer of 0 to 10; and t represents an integer of 1 to 3, where q is 2 or more and two R ｊ When two R ｊ may be joined together to form a ring structure, r is 2 or more, and two R ｋ When two R ｋ may be joined together to form a ring structure, s is 2 or more, and two R ｌ When two R ｌ may be joined together to form a ring structure, R ｍ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R ｇ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0006] <2> The method according to <1>, wherein the pulverized material is subjected to a winnowing separation treatment before the sorting. <3> The waste resin composition includes a thermoplastic resin B including one or more selected from the group consisting of a thermoplastic resin B1 including a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 including a structural unit (b-2) derived from a monomer represented by the general formula (1-2), and a thermoplastic resin B3 including a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin C including only the structural unit (c) derived from a monomer represented by the general formula (2), wherein the method includes: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B and the thermoplastic resin C using UV light. <4> The method according to <3>, wherein the pulverized material is subjected to a winnowing separation treatment before the sorting. <5> The waste resin composition comprises a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the general formulas (7) to (10), wherein the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B and the thermoplastic resin D by UV. <6> The method according to <5>, wherein the pulverized material is subjected to a winnowing separation treatment before the separation.<7> The waste resin composition includes a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and both a thermoplastic resin C containing only the structural unit (c) derived from a monomer represented by the general formula (2) and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the general formulas (7) to (10), the method comprising: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B, the thermoplastic resin C, and the thermoplastic resin D by UV light. <8> The method according to <7>, further comprising subjecting the pulverized material to a winnowing separation treatment before the separation. <9> The method according to <1>, wherein the thermoplastic resin B is a polycarbonate resin, a polyester carbonate resin, or a polyester resin. <10> The method according to <1>, wherein the thermoplastic resin C is a polycarbonate resin, a polyester carbonate resin, or a polyester resin. <11> The method according to <1>, wherein the thermoplastic resin B and the thermoplastic resin C are polycarbonate resins.

[0007] According to the method of the present invention, a highly pure recycled resin can be obtained from a waste resin composition.

[0008] The present invention will be described in detail below.

[0009] The present invention provides a method for producing recycled resin from a waste resin composition.

[0010] <Waste Resin Composition> In the method for producing a recycled resin from a waste resin composition of the present invention, the waste resin composition comprises: a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the following general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3); and at least one of a thermoplastic resin C containing only a structural unit (c) derived from a monomer represented by the following general formula (2), and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the following general formulas (7) to (10).

[0011] [In general formula (1-1), R ａ and R ｂ are each independently a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ is selected from 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; m and n each independently represent an integer of 0 to 5; X represents a single bond, —O—, —S—, —SO—, —SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of the groups is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. [In general formula (1-2), R ａ and Rｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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 and R 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, 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; 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, preferably a single bond or an optionally substituted fluorene group having a total of 12 to 20 carbon atoms; A and B each independently represent an optionally substituted alkylene group having 1 to 5 carbon atoms, preferably an alkylene group having 2 or 3 carbon atoms; 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; 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; 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, and 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 (phenoxy group). [In general formula (1-3), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent.]

[0012] [In general formula (2), R ｃ and R ｄ are each independently a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-Rｈ is selected from 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; p and q each independently represent an integer of 0 to 5; Y １ represents a single bond, —O—, —S—, —SO—, —SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R１５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of the groups is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. [In general formulas (7) to (10), X ｇ each independently represents an alkylene group having 1 to 10 carbon atoms; ｊ , R ｋ , and R ｌ each independently represents a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, and —C≡C—R ｉ is selected from R ｉ represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S; each p independently represents an integer of 0 or 1; each q, r, and s independently represents an integer of 0 to 10; and t represents an integer of 1 to 3, where q is 2 or more and two R ｊ When two R ｊ may be joined together to form a ring structure, r is 2 or more, and two R ｋ When two R ｋ may be joined together to form a ring structure, s is 2 or more, and two R ｌ When two R ｌmay be joined together to form a ring structure, R ｍ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R ｇ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0013] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0014] Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, an icosyl group, etc. Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, etc.

[0015] Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, an icosyloxy group, etc. Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, an decyloxy group, etc. Examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.

[0016] Examples of the cycloalkyl group 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 the cycloalkyl group 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.

[0017] Examples of the cycloalkoxy group having 5 to 20 carbon atoms include a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a cyclododecyloxy group, a cyclotridecyloxy group, a cyclotetradecyloxy group, a cyclopentadecyloxy group, a cyclooctadecyloxy group, a bicyclo[2.2.1]heptyloxy group, and a bicyclo[2.2.2]octyloxy group.

[0018] 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.

[0019] Examples of the heteroaryl group having 3 to 20 carbon atoms and containing one or more heterocyclic atoms selected from O, N, and S include a furanyl group, a benzofuranyl group, an isobenzofuranyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazyl group, a pyrrolidyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a naphthyridyl group, a quinoxalyl group, a quinazolyl group, a propanol ... Examples thereof include a teridyl 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.

[0020] 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 glycerinyloxy group, a pyrenyloxy group, a biphenyloxy group, a terphenyloxy group, a quaterphenyloxy group, etc. Examples of the aryloxy group having 6 to 10 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, etc.

[0021] R ｉrepresents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms and containing one or more heterocyclic atoms selected from O, N, and S. Examples of the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 3 to 20 carbon atoms and containing one or more heterocyclic atoms selected from O, N, and S include those mentioned above. Among these, R ｉ is preferably a phenyl group or a naphthyl group, more preferably a phenyl group, a 1-naphthyl group or a 2-naphthyl group.

[0022] Examples of the alkylene group having 1 to 10 carbon atoms include methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, pentylene, etc. Among these, methylene, ethylene, propylene, butylene, isobutylene, and sec-butylene are preferred, and methylene, ethylene, and propylene are more preferred.

[0023] In the above formula, the substituent in the case where "may have a substituent" is not particularly limited, but examples 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 cycloalkoxy 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, an amide group having 1 to 10 carbon atoms, and the like.

[0024] In an embodiment of the present invention, there is provided a method for producing recycled resin from a waste resin composition, wherein the waste resin composition comprises a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the general formula (1-1) above, a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2) above, and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3): a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin C containing only structural units (c) derived from a monomer represented by the general formula (2), and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the general formulas (7) to (10); and the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B, the thermoplastic resin C, and the thermoplastic resin D using UV light.

[0025] In one embodiment of the present invention, the waste resin composition comprises a thermoplastic resin B including one or more selected from the group consisting of a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the above general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the above general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin C containing only the structural unit (c) derived from a monomer represented by the above general formula (2). In this embodiment, there is provided a method for producing recycled resin from a waste resin composition, wherein the waste resin composition comprises a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the above general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the above general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin C containing only the structural unit (c) derived from a monomer represented by the above general formula (2), and the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B and the thermoplastic resin C using UV light.

[0026] In one embodiment of the present invention, the waste resin composition comprises a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the general formula (1-1) above, a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2) above, and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3): A thermoplastic resin B containing one or more structural units selected from the group consisting of a thermoplastic resin B3 containing at least one structural unit selected from the group consisting of the general formulas (7) to (10). In this embodiment, there is provided a method for producing recycled resin from a waste resin composition, wherein the waste resin composition comprises a thermoplastic resin B comprising one or more selected from the group consisting of a thermoplastic resin B1 comprising a structural unit (b-1) derived from a monomer represented by the above general formula (1-1), a thermoplastic resin B2 comprising a structural unit (b-2) derived from a monomer represented by the above general formula (1-2), and a thermoplastic resin B3 comprising a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin D comprising at least one structural unit selected from the group consisting of the above general formulas (7) to (10), and the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B and the thermoplastic resin D using UV light.

[0027] In one embodiment of the present invention, the waste resin composition comprises a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2), and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3). The thermoplastic resin B comprises one or more selected from the group consisting of a thermoplastic resin C containing only the structural unit (c) derived from a monomer represented by the general formula (2), and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the general formulas (7) to (10). In this embodiment, there is provided a method for producing recycled resin from a waste resin composition, wherein the waste resin composition comprises a thermoplastic resin B1 containing a structural unit (b-1) derived from a monomer represented by the general formula (1-1) above, a thermoplastic resin B2 containing a structural unit (b-2) derived from a monomer represented by the general formula (1-2) above, and a thermoplastic resin B3 containing a structural unit (b-3) derived from a monomer represented by the following general formula (1-3): a thermoplastic resin B containing one or more selected from the group consisting of a thermoplastic resin C containing only the structural unit (c) derived from a monomer represented by the general formula (2), and a thermoplastic resin D containing at least one structural unit selected from the group consisting of the general formulas (7) to (10); and the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B, the thermoplastic resin C, and the thermoplastic resin D using UV light.

[0028] Specific examples of the structural unit (b-1) derived from the monomer represented by formula (1-1) 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 "BHEBN"), 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene, etc. In one embodiment, the structural unit represented by formula (1-1) is a structural unit derived from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BHEBN).

[0029] Examples of the thermoplastic resin B1 include, but are not limited to, the following PC-1, PC-2, PC-4, and PC-7.

[0030] Specific examples of the structural unit (b-2) derived from the monomer represented by formula (1-2) include structural units derived from 2,2'-([1,1'-binaphthalene]-2,2'-diylbis(oxy))acetoacetic acid (BINOL-DC) and its methyl ester, ethyl ester, phenyl ester, etc.

[0031] Examples of the structural unit (b-2) derived from a monomer represented by formula (1-2) that constitutes the thermoplastic resin B2 include at least one structural unit derived from BINOL-DC and its methyl ester, ethyl ester, and phenyl ester.

[0032] Specific examples of the structural unit (b-3) derived from the monomer represented by formula (1-3) include structural units derived from naphthalene-2,6-dicarboxylic acid and its methyl ester, ethyl ester, phenyl ester, and the like.

[0033] In some embodiments, thermoplastic resin B1, thermoplastic resin B2, and thermoplastic resin B3 may each contain a structural unit (b-1) derived from a monomer represented by formula (1-1), a structural unit (b-2) derived from a monomer represented by formula (1-2), or a structural unit (b-3) derived from a monomer represented by formula (1-3), as well as a structural unit (b-4) derived from a monomer represented by formula (1-4) below. [In formula (1-4), 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 ｐ２each 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.

[0034] In formula (1-4), 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.

[0035] In formula (1-4), 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.

[0036] In formula (1-4), 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 ２Each independently represents an integer of 0 to 2, preferably 0 to 1. In formula (1-4), r ３ and r ４ each independently represents an integer of 0 to 1.

[0037] In the formula (1-4), 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.

[0038] 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 (1-4a) to (1-4c): General formula (1-4a) is a 9,9-bis(carboxyalkyl)fluorene, and in the above formula (1-4), r ３ and r ４ The general formula (1-4b) 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.

[0039] In the formula (1-4a), formula (1-4b), and formula (1-4c), G １ and G ２ , R ｐ１ and R ｐ２ , r １ and r ２ is defined as in formula (1-4).

[0040] Specific examples of monomers from which the structural unit represented by formula (1-4a) is derived include 9,9-bis(carboxyC2-6 alkyl)fluorenes, preferably 9,9-bis(carboxyC2-4 alkyl)fluorenes, more preferably 9,9-bis(carboxyC2-3 alkyl)fluorenes, as well as 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.

[0041] Specific examples of monomers from which the structural unit represented by formula (1-4b) is derived include 9,9-bis(carboxyC2-6 alkyl)-diphenylfluorenes, preferably 9,9-bis(carboxyC2-4 alkyl)-diphenylfluorenes, and more preferably 9,9-bis(carboxyC2-3 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.

[0042] Specific examples of monomers from which the structural unit represented by formula (1-4c) is derived include structural units derived from 9,9-bis(carboxyC2-6 alkyl)-dinaphthylfluorenes. In this case, the compound from which the structural unit is derived 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.

[0043] In some embodiments, the structural unit (b-4) includes a structural unit derived from 9,9-bis(2-carboxyethyl)fluorene, its alkyl ester having 1 to 20 carbon atoms (preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms), and an acid halide. In certain embodiments, the structural unit (b-4) includes a structural unit derived from 9,9-bis(2-carboxyethyl)fluorene.

[0044] Specific examples of the structural unit represented by formula (2) 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-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-te rt-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (also referred to as "BPPEF"), 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 (bisphenoxyethanolfluorene), bisphenol P-3MZ (4-[1-(4-hydroxyphenyl)-3-methylcyclohexyl]phenol), bisphenol OC-FL (4,4'-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol), bisphenol Z, BP-2EO (2,2'-[1,1'-biphenyl]-4,4'-diylbis(oxy)bisethanol), S-BOC(4,Examples of the structural unit include those derived from 4'-(1-methylethylidene)bis(2-methylphenol), TrisP-HAP (4,4',4''-ethylidene trisphenol), etc. In one embodiment, the structural unit represented by formula (2) is a structural unit derived from a compound selected from 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (BPPEF).

[0045] Examples of the thermoplastic resin C include, but are not limited to, the following PC-3, PC-5, and PC-6.

[0046] Examples of thermoplastic resins D containing at least one structural unit selected from the group consisting of general formulas (7) to (9) include aliphatic olefin resins such as COC (cycloolefin copolymer) and COP (cycloolefin polymer). Examples of such aliphatic olefin resins include, but are not limited to, APEL (registered trademark) manufactured by Mitsui Chemicals, Inc., TOPAS (registered trademark) manufactured by Polyplastics Co., Ltd., and ZEONEX (registered trademark) manufactured by Zeon Corporation.

[0047] Specific examples of the structural unit represented by formula (10) include structural units derived from decahydro-1,4:5'8-dimethanonaphthalene-2-methoxycarbonyl-6(7)-methanols. For example, structural units derived from a compound selected from decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6-methanol, decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-7-methanol, 2-methyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6-methanol, 2-methyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-7-methanol, 2-ethyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6-methanol, and 2-ethyl-decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-7-methanol can be mentioned.

[0048] In one embodiment of the present invention, when the thermoplastic resin D contains a structural unit represented by formula (10), it may be selected from a polycarbonate resin, a polyester resin, and a polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin D containing a structural unit represented by formula (10) contains a polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin D containing a structural unit represented by formula (10) contains a polyester resin. In yet another embodiment of the present invention, the thermoplastic resin D containing a structural unit represented by formula (10) contains a polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin D containing a structural unit represented by formula (10) is a polycarbonate resin.

[0049] In another embodiment of the present invention, the waste resin composition comprises a thermoplastic resin C containing only structural units (c) derived from a monomer represented by the following general formula (2), and a resin T containing structural units derived from naphthalenedicarboxylic acid, terephthalic acid, and derivatives thereof. In this embodiment, there is provided a method for producing recycled resin from a waste resin composition, wherein the waste resin composition comprises a thermoplastic resin C containing only structural units (c) derived from a monomer represented by the general formula (2) above, and a resin T containing structural units derived from naphthalenedicarboxylic acid, terephthalic acid, and derivatives thereof, and the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin C and the resin T using UV light.

[0050] [In general formula (2), R ｃ and R ｄ are each independently a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ is selected from 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; p and q each independently represent an integer of 0 to 5; Y １ represents a single bond, —O—, —S—, —SO—, —SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of the groups is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10.

[0051] The resin T may be, but is not limited to, a polyester obtained from BPEF (bisphenoxyethanolfluorene, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene) and naphthalenedicarboxylic acid, or a polyester carbonate obtained from BPEF, terephthalic acid, and dipropionic acid fluorene.

[0052] In the present invention, the waste resin composition may be one that is discharged after molding of a spool, a runner, or the like, or may be an unused or used resin composition.

[0053] In one embodiment of the present invention, the thermoplastic resin B may be selected from polycarbonate resin, polyester resin, and polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin B comprises a polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin B comprises a polyester resin. In yet another embodiment of the present invention, the thermoplastic resin B comprises a polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin B is a polycarbonate resin.

[0054] In one embodiment of the present invention, the thermoplastic resin C may be selected from a polycarbonate resin, a polyester resin, and a polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin C comprises a polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin C comprises a polyester resin. In yet another embodiment of the present invention, the thermoplastic resin C comprises a polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin C is a polycarbonate resin.

[0055] In one embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C may be independently selected from a polycarbonate resin, a polyester resin, and a polyester carbonate resin. In one embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C comprise a polycarbonate resin. In another embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C comprise a polyester resin. In yet another embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C comprise a polyester carbonate resin. In a preferred embodiment of the present invention, the thermoplastic resin B and the thermoplastic resin C are polycarbonate resins.

[0056] <Pulverization Step> In the method of the present invention, pulverizing the waste resin composition to obtain a pulverized material is carried out by pulverizing spools, runners, etc. recovered as waste resin material using a pulverizer or the like. Pulverization of spools, runners, etc. can be carried out using a pulverizer such as a single-shaft pulverizer, a double-shaft pulverizer, a triple-shaft pulverizer, or a cutter mill. The pulverized material obtained by pulverization is, for example, in the form of flakes, powder, or lumps. However, since the majority of spools, runners, etc. are thin, having a thickness of 1 cm or less, the majority of the pulverized material is usually in the form of flakes or fine powder. Note that flaky pulverized material refers to thin or flat pulverized material having a thickness of about 5 mm or less, and fine powder pulverized material refers to pulverized material having a size of about 1 mm or less.

[0057] <Sorting by UV> In the method of the present invention, the thermoplastic resin B and the thermoplastic resin C are separated by UV by feeding the pulverized material into a UV sorter. For example, by setting the pulverized material that does not change color upon UV irradiation to be hit with an air gun and not to be hit with a pulverized material that changes color upon UV irradiation, it is possible to separate the pulverized material that does not change color upon UV irradiation from the pulverized material that does change color upon UV irradiation. The determination of whether or not a pulverized material changes color upon UV irradiation can be performed visually or using a detector. Any detector can be used as long as it can irradiate the pulverized material with UV light, compare it with a comparison color plate, record the position of the pulverized material that glows or does not glow with a camera, and hit the target for removal with an air gun based on the position information. Examples of such detectors include, but are not limited to, a rheosorter.

[0058] The conditions for sorting by UV can be set appropriately depending on the resin to be sorted. For example, the wavelength used for irradiation can be selected so that the resin to be sorted emits light but the impurity resin does not emit light. The discharge amount, sensitivity, conveyor belt speed, etc. of the UV sorter can also be set appropriately.

[0059] A comparison color board may be used in the UV sorter. For example, by using white paper that develops color under UV light, which contains a fluorescent whitening agent and glows blue when irradiated with UV light, a "glowing blue" base can be used and a "non-glowing resin" can be applied in comparison. Without white paper, i.e., without using a comparison color board, the base will be a dark "black," and materials that glow blue under UV light or that do not glow (weakly glow) can be rejected.

[0060] In the method of the present invention, thermoplastic resin B contains a naphthalene ring and therefore emits light when irradiated with UV light, whereas thermoplastic resin C, thermoplastic resin D, and resin T do not contain a naphthalene ring and therefore do not emit light or emit light only weakly when irradiated with UV light. Based on this, thermoplastic resin B can be distinguished from thermoplastic resin C, thermoplastic resin D, and resin T using UV light.

[0061] <Pretreatment Step> In the method of the present invention, gravity sorting, which utilizes the differences in specific gravity of multiple resins, can be used as a pretreatment before the sorting. Examples of such pretreatment include, but are not limited to, a winnowing separation method in which the pulverized material is sorted by wind power, a method in which the pulverized material is immersed in a liquid such as water and sorted based on the difference in specific gravity of the pulverized material relative to the liquid, and a method in which the pulverized material is subjected to a certain amount of vibration to separate and sort pulverized material with different specific gravities. In particular, when the pulverized material is finely powdered or smooth, performing pretreatment can improve the sorting efficiency in a UV sorter.

[0062] Wind separation is a method in which, for example, in a separator capable of generating a rotating air current inside, crushed materials are exposed to the air current generated by the separator, and are separated and recovered into those with a high specific gravity or a small specific surface area that fall naturally under their own weight, and those with a low specific gravity or a large specific surface area that are lifted up by the air current.

[0063] In this method, crushed resins with a high specific gravity or a small specific surface area fall naturally under their own weight, while crushed resins with a low specific gravity or a large specific surface area are lifted up, making it possible to separate and recover resins with a high specific gravity or a small specific surface area from resins with a low specific gravity or a large specific surface area.

[0064] In this type of winnowing, the same operation may be repeated for the same pulverized material. For example, the material that has fallen naturally may be further winnowed to increase the content of resins with high specific gravity or small specific surface area in the recycled resins with high specific gravity or small specific surface area.

[0065] In a preferred embodiment of the present invention, the method of the present invention includes subjecting the ground material to winnowing, which may be carried out in one pass, two passes, or more.

[0066] <Granulation Step> The collected roughly recycled resin is preferably granulated into pellets to facilitate handling during molding and other processes.

[0067] In the granulation step, the pulverized material is preferably plasticized and granulated by melt blending. Granulation devices for plasticization and granulation include single-screw extruders, twin-screw extruders, and multi-screw extruders, but any known device can be used. The shape of the pellets is preferably cylindrical, spherical, or elliptical.

[0068] The granulation is preferably carried out, for example, by extruding the plasticized recycled resin into strands, cutting them into pellets using a pelletizer while cooling them in a water bath. The pellets removed from the water bath are usually dried to remove moisture adhering to the surface.

[0069] After UV treatment, the recovered crude recycled resin can be reused after granulation as described above.

[0070] Alternatively, after UV treatment, the recovered crude recycled resin can be subjected to the following steps (i) removing impurities contained in the waste resin composition and (ii) producing a recycled resin.

[0071] <Step (i)> Step (i) is a step of removing impurities contained in the waste composition. The molded waste contained in the waste composition may contain two or more resins. In addition, the waste composition 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 waste composition.

[0072] The method for removing impurities contained in the waste composition 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.

[0073] 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.

[0074] For example, if the impurities are metals, they can be removed by a method using magnetic force. Specifically, by using a magnet or a metal detector, metals that may be contained in the waste composition can be removed.

[0075] Other methods that can be applied include a method of removing impurities using salt water to exploit the difference in buoyancy, a method of removing impurities using activated carbon to exploit the difference in adsorption power, and a method of removing impurities using hydrocyclone treatment to exploit the difference in specific gravity.

[0076] As a method utilizing the difference in chemical properties between the target resin and impurities, there is a method of depolymerizing the target resin.

[0077] For example, a resin having a structural unit derived from at least one monomer selected from the group consisting of the general formulae (1-1), (1-2), (2), and (10) can be depolymerized by treating it with an alkaline aqueous solution to obtain at least one dihydroxy compound (depolymerized monomer) selected from the group consisting of the general formulae (1-1), (1-2), (2), and (10).

[0078] On the other hand, impurity resins having structural units derived from at least one monomer selected from the group consisting of general formulas (7) to (9) are not depolymerized even when treated with an alkaline aqueous solution.

[0079] Therefore, when a waste composition contains a resin having a structural unit derived from at least one monomer selected from the group consisting of general formulas (1-1), (1-2), (2), and (10), and an impurity resin having a structural unit derived from at least one monomer selected from the group consisting of general formulas (7) to (9), when the waste composition is treated with an alkaline aqueous solution, only the resin having a structural unit derived from at least one monomer selected from the group consisting of general formulas (1-1), (1-2), (2), and (10) is depolymerized.

[0080] The resulting dihydroxy compound (depolymerized monomer) has properties significantly different from those of an impurity resin having a constitutional unit derived from at least one monomer selected from the group consisting of general formulas (7) to (9), and therefore, the impurity resin can be removed.

[0081] 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.

[0082] The reaction solvent is not particularly limited, but examples thereof include aliphatic hydrocarbon solvents and aromatic hydrocarbon solvents.

[0083] The aliphatic hydrocarbon solvent is not particularly limited, but examples thereof include pentane, hexane, heptane, octane, nonane, decane, cyclohexane, and cyclodecane.

[0084] The aromatic hydrocarbon solvent is not particularly limited, but examples thereof include toluene, xylene, and mesityle.

[0085] 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.

[0086] 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.

[0087] The alkaline aqueous solution contains a metal oxide and water.

[0088] The metal oxide is not particularly limited, but examples thereof include alkali metals such as sodium hydroxide, potassium hydroxide, and rubidium hydroxide; and alkaline earth metals such as calcium hydroxide and barium hydroxide. Among these, the metal oxide is preferably an alkali metal, more preferably sodium hydroxide or potassium hydroxide, and even more preferably potassium hydroxide. These metal oxides may be used alone or in combination of two or more.

[0089] The amount of the metal oxide 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. A metal oxide used in an amount of 1.5 mol or more is preferred because depolymerization is sufficiently carried out. On the other hand, a metal oxide used in an amount of 10 mol or less is preferred because production costs are reduced.

[0090] The concentration of the metal oxide 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 oxide concentration of 10% by mass or more is preferred because it increases the depolymerization reaction rate. On the other hand, a metal oxide concentration of 60% by mass or less is preferred because it prevents the alkaline aqueous solution from becoming a slurry and facilitates the reaction.

[0091] 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.

[0092] <Step (ii)> Step (ii) is a step of producing a recycled resin.

[0093] In the step (ii), when 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.

[0094] On the other hand, when the impurities are removed by a method utilizing the difference in chemical properties between the target resin and the impurities, the depolymerized monomer of the target resin can be polymerized to produce a recycled resin. In this case, the recycled resin produced may be the same as or different from the target resin contained in the waste composition.

[0095] The method for producing a recycled resin by polymerizing a depolymerized monomer of the target resin is not particularly limited, and the recycled resin can be produced by a known method. For example, when the depolymerized monomer is at least one dihydroxy compound selected from the group consisting of monomers derived from the above general formulas (1-1), (1-2), (2), and (10), the recycled resin can be produced by subjecting the dihydroxy compound 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.

[0096] 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.

[0097] 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.

[0098] The basic compound catalyst is not particularly limited, but examples thereof include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] The above-mentioned basic compound catalysts and transesterification catalysts may be used alone or in combination of two or more kinds.

[0104] 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.

[0105] In the melt polycondensation method, it is desirable to melt a dihydroxy compound and a carbonate diester in a reaction vessel and then carry out the reaction in a state in which the produced monohydroxy compound remains. In order to retain the monohydroxy compound, the pressure can be controlled by, for example, closing the reaction vessel or reducing or increasing the pressure.

[0106] In the method for producing recycled resin of the present invention, steps other than those described above may be performed, and a washing step may be performed to remove contents adhering to the inside of the multilayer hollow container. Washing is preferably performed by rinsing with a liquid, and washing with water, washing with an alkaline aqueous solution, or both may be performed.

[0107] The washing may be carried out before or after the multilayer hollow container is crushed into a crushed material, but is preferably carried out before any of granulation, crystallization, and solid-state polymerization. Furthermore, the washing step may be carried out simultaneously with the crushing step using a crusher called a wet crusher, which performs both washing and crushing at the same time.

[0108] Furthermore, when a washing step is performed, a drying step may be performed after the washing step. By performing the drying step, the moisture content of the recycled resin obtained by this method can be reduced, making it possible to provide a high-quality recycled resin with high thermal stability, etc. The drying step can be performed using, for example, air blown by a dryer or hot air, etc.

[0109] When the method for producing recycled resin includes a step of removing impurity resins, the content of impurity resins in the obtained recycled resin is preferably less than 1 mass %, more preferably less than 0.8 mass %, and even more preferably less than 0.6 mass %. By reducing the content of impurity resins in this way, the quality of the recycled resin becomes good.

[0110] The present invention will be described in more detail below using examples and comparative examples, but it is not intended that the present invention be limited to the following examples.

[0111] <Waste Resin Composition> The thermoplastic resins contained in the waste resin compositions used in the Examples and Comparative Examples are as follows.

[0112] <Wind separation treatment / pretreatment> (Example a) After molding PC-1, the discharged spool and runner were pulverized in a pulverizer to obtain pulverized material. The pulverized material contained 10% by mass of fine powder of 850 μm or less. The pulverized material was blown with air at a throughput rate of 600 kg / hr and an inverter speed of 22 Hz to remove the fine powder (first pass of winnowing separation treatment). The resulting resin (pulverized material) was further blown with air under the same conditions to remove the fine powder (second pass of winnowing separation treatment). Furthermore, the winnowing treatment removed not only the fine powder but also smooth-shaped particles such as lens fragments. The results for the resulting resin (pulverized material) are shown in Table 1.

[0113] Examples b and c The winnowing separation treatment was carried out in the same manner as in Example a, except that the resin type and the conditions for the winnowing separation treatment were changed as shown in Table 1.

[0114]

[0115] <Preparation of sample for UV sorting test> The ground material PC-1 (9950 g) obtained by the above-mentioned winnowing separation treatment (Example a) and PC-5 (50 g) obtained by the above-mentioned winnowing separation treatment (Example c) were charged into a blender, that is, charged into the blender so that the PC-5 concentration in the sample was 5000 ppm, and mixed for 15 minutes to obtain a test sample.

[0116] <UV Sorting> (Example 1) The test samples described above were placed flat on a conveyor belt and continuously fed into a UV sorter. The crushed product (PC-5) that does not develop color under UV light was hit with an air gun, while the crushed product (PC-1) that does develop color under UV light was not hit with an air gun, and purified crushed PC-1 was obtained.

[0117] White paper that develops color under UV light was used as a comparison color plate (background). This white paper contains a fluorescent whitening agent and glows blue when irradiated with UV light. This was utilized to set the "glowing blue" as the base and to compare it with the "non-glowing resin." The UV sorting machine conditions and the physical properties of the resulting resin are shown in Table 2.

[0118] (Examples 2 to 9) Purified crushed PC-1 products were obtained in the same manner as in Example 1, except that the concentration of PC-5 and the UV sorting conditions were as shown in Table 2. The UV sorting conditions and the physical properties of the obtained resins are shown in Table 2.

[0119] (Examples A to I) Purified crushed resin products were obtained in the same manner as in Example 1, except that the resin concentrations and UV sorting conditions were as shown in Tables 3-1, 3-2, 3-3, 3-4, 4-1, 4-2, 4-3, and 4-4. The UV sorter conditions and the physical properties of the obtained resins are shown in Tables 3-1, 3-2, 3-3, 3-4, 4-1, 4-2, 4-3, and 4-4.

[0120] (Examples 1-1, 2-1, 3-1) The same procedures as in Examples 1 to 3 were carried out, except that white paper was not used as a comparative color plate (background). When white paper was not used, the base was dark, i.e., "black," and it was possible to filter out materials that emit blue light when irradiated with UV light or that do not emit light (weak light emission). The conditions of the UV sorter and the physical properties of the obtained crushed products are shown in Table 2.

[0121] <Removal rate> 50 g of crushed product samples were laid out flat and irradiated with 222 nm ultraviolet light (UV-C). Those that emitted light visually (PC-1, PC-2, PC-4, PC-7) were separated from those that did not emit light (COC (cycloolefin copolymer), PC-3, PC-5, PC-6, PC-8), and the object to be removed (PC-5) was picked up visually and its weight was measured. The removal rate was calculated using the following formula 1: Removal rate (%) = weight of picked up object to be removed / 50 × 100 (Formula 1)

[0122] <Yield (%)> Yield (%) = Amount of refined crushed product (kg) / Amount processed (kg) × 100

[0123] <Concentration (ppm) of substance to be removed in refined crushed product> Concentration (ppm) of substance to be removed in refined crushed product=Amount (g) of substance to be removed contained in 50 g of refined crushed product / 50×1,000,000

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] As described above, it has been demonstrated that the method of the present invention makes it possible to obtain a highly pure recycled resin from a waste resin composition by removing debris containing impurities.

Claims

1. A method for producing a recycled resin from a waste resin composition, the waste resin composition comprising: a thermoplastic resin B comprising one or more selected from the group consisting of a thermoplastic resin B1 comprising a structural unit (b-1) derived from a monomer represented by the following general formula (1-1), a thermoplastic resin B2 comprising a structural unit (b-2) derived from a monomer represented by the following general formula (1-2), and a thermoplastic resin B3 comprising a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and at least one of a thermoplastic resin C comprising only a structural unit (c) derived from a monomer represented by the following general formula (2), and a thermoplastic resin D comprising at least one structural unit selected from the group consisting of the following general formulas (7) to (10), the method comprising: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B, the thermoplastic resin C, and the thermoplastic resin D by UV. [In general formula (1-1), R ａ and R ｂ each independently represents a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ is selected from 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; m and n each independently represent an integer of 0 to 5; X represents a single bond, -O-, -S-, -SO-, -SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０ each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded together to form a carbon ring having 3 to 20 carbon atoms or a heterocycle having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of A and B is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. [In general formula (1-2), 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 alkoxy 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 cycloalkoxy 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 are each independently an alkylene group having 1 to 5 carbon atoms which may have a substituent; m and n are each independently an integer of 0 to 6, preferably an integer of 0 to 3; a and b are each independently an integer of 0 to 10, preferably an integer of 1 to 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. [In the general formula (1-3), R' and R'' are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent.] [In general formula (2), R ｃ and R ｄ each independently represents a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy 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 cycloalkoxy 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, or an aryloxy group having 6 to 20 carbon atoms which may have a substituent, and -C≡C-R ｈ is selected from 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; p and q each independently represent an integer of 0 to 5; Y １ represents a single bond, -O-, -S-, -SO-, -SO ２ -, -CO-, or a divalent group represented by any one of the following general formulas (3) to (6): (In general formulas (3) to (6), R ９ and R １０ each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or ９ and R １０ are bonded together to form a carbon ring having 3 to 20 carbon atoms or a heterocycle having 1 to 20 carbon atoms; c represents an integer of 0 to 20; R １１ and R １２ each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １１ and R １２ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １３ ~R １６ each independently represents hydrogen, a halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or １３ and R １４ and R １５ and R １６ are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; R １７ ~R ２６ each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms; R １７ ~R ２６ At least one of A and B is an alkyl group having 1 to 3 carbon atoms. A and B each independently represent a saturated hydrocarbon group having 1 to 5 carbon atoms, and a and b each independently represent an integer of 0 to 10. [In general formulas (7) to (10), X ｇ each independently represents an alkylene group having 1 to 10 carbon atoms; R ｊ , R ｋ , and R ｌ each independently represents a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, and -C≡C-R ｉ is selected from ｉ represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S; each p independently represents an integer of 0 or 1; each q, r, and s independently represents an integer of 0 to 10; and t represents an integer of 1 to 3, where q is 2 or more and two R ｊ When R are on adjacent carbon atoms, two R ｊ may be joined together to form a ring structure, r is 2 or more, and two R ｋ When R are on adjacent carbon atoms, two R ｋ may be joined together to form a ring structure, s is 2 or more, and two R ｌ When R are on adjacent carbon atoms, two R ｌ may be taken together to form a ring structure, R ｍ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R ｇ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

2. The method of claim 1, wherein the ground material is winnowed prior to said screening.

3. The method according to claim 1, wherein the waste resin composition comprises a thermoplastic resin B comprising one or more selected from the group consisting of a thermoplastic resin B1 comprising a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 comprising a structural unit (b-2) derived from a monomer represented by the following general formula (1-2), and a thermoplastic resin B3 comprising a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin C comprising only the structural unit (c) derived from a monomer represented by the general formula (2), the method comprising: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B and the thermoplastic resin C by UV.

4. The method of claim 3, wherein the ground material is winnowed prior to said screening.

5. The method according to claim 1, wherein the waste resin composition comprises a thermoplastic resin B comprising one or more selected from the group consisting of a thermoplastic resin B1 comprising a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 comprising a structural unit (b-2) derived from a monomer represented by the following general formula (1-2), and a thermoplastic resin B3 comprising a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin D comprising at least one structural unit selected from the group consisting of the general formulas (7) to (10), wherein the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B and the thermoplastic resin D by UV.

6. The method of claim 5, wherein the ground material is winnowed prior to said screening.

7. The method according to claim 1, wherein the waste resin composition comprises a thermoplastic resin B comprising one or more selected from the group consisting of a thermoplastic resin B1 comprising a structural unit (b-1) derived from a monomer represented by the general formula (1-1), a thermoplastic resin B2 comprising a structural unit (b-2) derived from a monomer represented by the following general formula (1-2), and a thermoplastic resin B3 comprising a structural unit (b-3) derived from a monomer represented by the following general formula (1-3), and a thermoplastic resin C comprising only the structural unit (c) derived from a monomer represented by the general formula (2), and a thermoplastic resin D comprising at least one structural unit selected from the group consisting of the general formulas (7) to (10). The method according to claim 1, wherein the method comprises: pulverizing the waste resin composition to obtain a pulverized material; and separating the thermoplastic resin B, the thermoplastic resin C, and the thermoplastic resin D by UV.

8. The method of claim 7, wherein the ground material is winnowed prior to said screening.

9. The method according to claim 1, wherein the thermoplastic resin B is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

10. The method according to claim 1, wherein the thermoplastic resin C is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

11. The method of claim 1, wherein said thermoplastic resin B and said thermoplastic resin C are polycarbonate resins.

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