WO2022118930A1

WO2022118930A1 - Composition, composition for resin coloring, and polymer

Info

Publication number: WO2022118930A1
Application number: PCT/JP2021/044341
Authority: WO
Inventors: 由記福田
Original assignee: 富士フイルム株式会社; 富士フイルム和光純薬株式会社
Priority date: 2020-12-03
Filing date: 2021-12-02
Publication date: 2022-06-09
Also published as: JPWO2022118930A1

Abstract

A first problem of the present invention is to provide a composition having excellent sweat resistance. A second problem of the present invention is to provide a composition for resin coloring and a polymer which have excellent sweat resistance. These compositions of the present invention each comprise a polymer comprising repeating units represented by general formula (1) and repeating units represented by general formula (2) and a thermoplastic resin.

Description

Compositions, resin coloring compositions, polymers

The present invention relates to a composition, a resin coloring composition, and a polymer.

Recently, colored resin molded products are used in various fields.
Examples of the main coloring method of the resin include a method of directly mixing the dye and the resin so as to obtain a desired color, and a method of passing through a masterbatch for coloring the resin. The method via a resin coloring masterbatch is specifically described above in which a composition (for example, pellets) in which a dye and a resin are mixed so as to have a high dye concentration is used as a resin coloring masterbatch. This is a method of mixing a masterbatch for resin coloring and a diluted resin so as to obtain a desired color.

A compound having a coumarin skeleton (hereinafter, also referred to as “coumarin compound”) is mainly used as a dye exhibiting a fluorescent yellow color. For example, Patent Document 1 discloses a low molecular weight coumarin compound shown below. ing.

Further, Patent Document 2 discloses the following low-molecular-weight coumarin compounds.

Japanese Unexamined Patent Publication No. 2020-007383 Japanese Unexamined Patent Publication No. 2010-168369

By the way, the colored resin molded product has a wide range of uses, for example, it may be used as a decorative item or the like to be worn on the skin. Therefore, there is also a demand for performance that does not easily fade due to sweat from the user (excellent in sweat resistance).

The present inventor prepared and examined a composition in which the coumarin compound described in Patent Documents 1 and 2 was mixed with a resin as a dye, and it was clarified that the sweat resistance may not meet the recent requirements. did.

Therefore, it is an object of the present invention to provide a composition having excellent sweat resistance.
Another object of the present invention is to provide a resin coloring composition and a polymer having excellent sweat resistance.

As a result of diligent studies on the above problems, the present inventors have found that the above problems can be solved by the following configuration, and have completed the present invention.

[1] A polymer containing a repeating unit represented by the general formula (1) described later and a repeating unit represented by the general formula (2) described later.
A composition comprising a thermoplastic resin.
[2] The composition according to [1], wherein the repeating unit represented by the general formula (1) is a repeating unit represented by the general formula (4) described later.
[3] In the above general formula (2), R ² represents a group represented by the general formula (R1A) described later, and R ³ represents a hydrogen atom or a methyl group, in [1] or [2]. The composition described.
[4] The repeating unit represented by the general formula (1) is the repeating unit represented by the general formula (5) described later, and the repeating unit represented by the general formula (2) is the general unit described later. The composition according to [1] or [2], which is a repeating unit represented by the formula (6).
[5] In the above general formula (6), R ³ represents a hydrogen atom or a methyl group, and R ¹⁵ may have a substituent, an aryl group, a benzyl group, an alkyl group, or hydrogen. The composition according to [4], which represents an atom.
[6] The composition according to any one of [1] to [5], wherein the thermoplastic resin is at least one selected from the group consisting of a polyamide resin and a polyolefin resin.
[7] The above polymer is
The weight average molecular weight is 1,000 to 100,000, and
The description according to any one of [1] to [6], wherein the content of the repeating unit represented by the general formula (1) is 0.1 to 50% by mass with respect to all the repeating units in the polymer. Composition.
[8] A resin coloring composition comprising the composition according to any one of [1] to [7].
[9] A polymer containing a repeating unit represented by the general formula (4) described later and a repeating unit represented by the general formula (2) described later.
[10] The repeating unit represented by the general formula (4) is the repeating unit represented by the general formula (5) described later, and the repeating unit represented by the general formula (2) is the general unit described later. The polymer according to [9], which is a repeating unit represented by the formula (6).
[11] In the above general formula (6), R ³ represents a hydrogen atom or a methyl group, and R ¹⁵ may have a substituent, an aryl group, a benzyl group, an alkyl group, or hydrogen. The polymer according to [10], which represents an atom.
[12] The weight average molecular weight is 1,000 to 100,000, and the weight average molecular weight is 1,000 to 100,000.
The description according to any one of [9] to [11], wherein the content of the repeating unit represented by the general formula (4) is 0.1 to 50% by mass with respect to all the repeating units in the polymer. polymer.

According to the present invention, it is possible to provide a composition having excellent sweat resistance.
Further, according to the present invention, it is possible to provide a resin coloring composition and a polymer having excellent sweat resistance.

Hereinafter, the present invention will be described in detail.
The description of the constituent elements described below may be based on the representative embodiments of the present invention, but the present invention is not limited to such embodiments.
In the present specification, with respect to a substituent or the like for which substitution or non-substitution is not specified, the group is further substituted with a substituent (for example, a substituent W described later) as long as the desired effect is not impaired. May be. For example, the notation "alkyl group" means an alkyl group that may be substituted with a substituent (eg, a substituent W described below). Further, the "organic group" in the present specification means a group containing at least one carbon atom.
Further, in the present specification, the numerical range represented by using "-" means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
The bonding direction of the divalent group described in the present specification is not particularly limited, and for example, in the case of -CO-O-, it may be either -CO-O- or -O-CO-.
As used herein, (meth) acrylate represents acrylate and methacrylate, and (meth) acrylic represents acrylic and methacrylic.
In the present specification, the weight average molecular weight (Mw) and the degree of dispersion (also referred to as molecular weight distribution) (Mw / Mn) of the polymer are measured by GPC (solvent: tetrahydrofuran) by a GPC (Gel Permeation Chromatography) apparatus (HLC-8220GPC manufactured by Tosoh). , Flow rate (sample injection amount): 10 μL, Column: TSK gel polymer HXL-M manufactured by Toso Co., Ltd., Column temperature: 40 ° C., Flow velocity: 1.0 mL / min, Detector: Differential refractometer (Refractometer) Defined as a polystyrene equivalent value by.

[Composition]
The composition of the present invention comprises a polymer (hereinafter, also referred to as “specific polymer”) containing a repeating unit represented by the general formula (1) described later and a repeating unit represented by the general formula (2) described later, and heat. Including, with a plastic resin.
With the above configuration, the composition of the present invention exhibits excellent sweat resistance.
A feature of the present invention as compared with the prior art is that a specific polymer containing a coumarin dye as a repeating unit is used. Although the mechanism of action of the effect of the present invention is not clear, the specific polymer containing the coumarin dye in the structure forms a network with the thermoplastic resin, so that the coumarin dye is less likely to be attached or detached by sweat, resulting in fading. It is presumed that it is unlikely to occur.
Further, according to the present invention of the present inventor, the above composition is capable of stably coloring a resin even when a specific polymer is blended in a relatively high concentration, and is a resin coloring composition (resin coloring masterbatch). ), It is also clarified that it can be suitably used. Further, it has been clarified that the light resistance is also excellent by appropriately selecting the repeating unit represented by the general formula (2) in the specific polymer.
Hereinafter, the fact that the composition is more excellent in sweat resistance and / or light resistance is also referred to as "the effect of the present invention is more excellent".

Hereinafter, the composition of the present invention will be described.
The composition of the present invention comprises a specific polymer and a thermoplastic resin.

[Specific polymer]
Hereinafter, the specific polymer will be described.
The specific polymer is a polymer containing a repeating unit represented by the following general formula (1) and a repeating unit represented by the following general formula (2).
In the following, first, the repeating unit represented by the general formula (1) will be described.

In the general formula (1), R ¹ represents a hydrogen atom or a substituent.
The type of the substituent represented by R ¹ is not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
R ¹ preferably represents an alkyl group which may have a hydrogen atom or a substituent, and may have a hydrogen atom or a substituent, because the effect of the present invention is more excellent. It is more preferable to represent a good alkyl group having 1 to 6 carbon atoms, and even more preferably to represent a hydrogen atom or a methyl group. In addition, examples of the substituent that the above-mentioned alkyl group may have include the groups exemplified by the substituent W described later.

L represents a divalent linking group.
The divalent linking group represented by L is not particularly limited, and is, for example, -CO-, -O-, -S-, -SO-, _-SO2- , -NR ^A- , and an alkylene group (straight chain). It may be in the form of a branched chain, a branched chain, or a cyclic chain. It is preferably 1 to 15 carbon atoms, more preferably 1 to 6 carbon atoms), an alkenylene group (preferably 2 to 6 carbon atoms), and a divalent aliphatic. A heterocyclic group (preferably a 5- to 10-membered ring having at least one nitrogen atom, an oxygen atom, or a sulfur atom in the ring structure, more preferably a 5- to 7-membered ring, and even more preferably a 5- to 6-membered ring). A divalent arylene group (preferably a 6-10 membered ring, more preferably a 6 membered ring) and a divalent heteroarylene group (5- to 5 having at least one nitrogen atom, oxygen atom, or sulfur atom in the ring structure). A 10-membered ring is preferable, a 5- to 7-membered ring is more preferable, and a 5- to 6-membered ring is more preferable), and a divalent linking group in which a plurality of these are combined can be mentioned.
Examples of the ^RA include a hydrogen atom or a monovalent organic group. The monovalent organic group is not particularly limited, but for example, an alkyl group (preferably 1 to 6 carbon atoms) is preferable.
Further, the alkylene group, the alkenylene group, the divalent aliphatic heterocyclic group, the divalent arylene group, and the divalent heteroarylene group may have a substituent. Examples of the substituent include the groups exemplified by the substituent W described later.

As the divalent linking group represented by L, the effect of the present invention is more excellent, and among them, -CO-O-, an alkylene group, a divalent arylene group, a divalent heteroarylene group, or these. It is preferable that it is a divalent linking group in which a plurality of the above is combined, and it is more preferable that it is a —CO—O—, an alkylene group, a divalent arylene group, or a divalent linking group in which a plurality of these is combined. A divalent linking group in which an alkylene group and a divalent arylene group are combined (for example, * _-CH2 -Ph- * (Ph represents a phenylene group which may have a substituent, * represents a bonding position). It is more preferable.

X ¹ represents a residue derived from the compound represented by the following general formula (3).

In the general formula (3), X ² represents a coumarin ring group which may have a substituent.
The coumarin ring group which may have a substituent is intended to be a group formed by removing one hydrogen atom from the coumarin ring which may have a substituent. The position where the hydrogen atom is excluded is not particularly limited, and may be a hydrogen atom bonded to a carbon atom constituting the coumarin ring (in other words, a carbon atom which is a ring member atom of the coumarin ring) or a coumarin ring. It may be a hydrogen atom contained in the substituent of. Examples of the coumarin ring group which may have a substituent include residues derived from the compound represented by the following general formula (3A).

In the general formula (3A), R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁶ each independently represent a hydrogen atom or a substituent. However, at least one of R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁶ in the general formula (3A) represents a hydrogen atom, and one of the above hydrogen atoms is removed. Residues derived from the compound represented by the general formula (3A) are formed. That is, the position where one of the hydrogen atoms is removed is the bond position with = C− adjacent to X ² specified in the general formula (3). Among them, in that the effect of the present invention is more excellent, R ^{16 in the general formula (3A) represents a hydrogen atom, and the hydrogen atom of R 16} ^is removed to form a compound represented by the general formula (3A). It is preferable that the derived residue is formed.
The substituents represented by R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , and R ¹⁶ are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later. In particular, it is preferable that at least one of R ⁹ , R ¹⁰ , R ¹¹ and R ¹² has a substituent, and it is more preferable that the substituent has a dialkylamine having a total carbon number of 2 to 8.
Further, in R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁶ , adjacent substituents may be bonded to each other to form a ring.

In the general formula (3), Y represents an oxygen atom, a sulfur atom, or NR ⁸ .
As Y, it is preferable to represent NR ⁸ in that the effect of the present invention is more excellent.

In the general formula (3), R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom or a substituent. However, at least one of R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ in the general formula (3) represents a hydrogen atom, and one of the above hydrogen atoms is removed, so that the general formula ( Residues derived from the compound represented by 3) are formed. That is, the position where one of the hydrogen atoms is removed is the bond position with L specified in the general formula (1). When only R ⁸ among R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ represents a hydrogen atom, Y in the above general formula (3) represents NR ⁸ .
In that the effect of the present invention is more excellent, Y in the general formula (3) is NR ⁸ and R ⁸ represents a hydrogen atom, and the hydrogen atom of this R ⁸ is removed, so that the general formula (3) can be used. Residues derived from the represented compound are formed, or at least one of R ⁵ and R ⁶ represents a hydrogen atom and one of at least one hydrogen atom of R ⁵ and R ⁶ is removed. Therefore, it is preferable that a residue derived from the compound represented by the general formula (3) is formed, and Y in the general formula ( ³ ) is NR ⁸ and R ⁸ represents a hydrogen atom. It is more preferable that a residue derived from the compound represented by the general formula (3) is formed by removing the hydrogen atom of.
The substituents represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
As ^R4 , ^R5 , ^R6 , ^R7 , and ^R8 , it is preferable to represent a hydrogen atom.

As the repeating unit represented by the above-mentioned general formula (1), the repeating unit represented by the following general formula (4) is preferable, and the repeating unit represented by the following general formula (5) is preferable. It is more preferable to have it.

In the general formula (4), R ⁴ , R ⁵ , R ⁶ and R ⁷ are synonymous with R ⁴ , R ⁵ , R ⁶ and R ⁷ in the above-mentioned general formula (3), and preferred embodiments are also included. It is the same.
In the general formula (4), R ¹ and L are synonymous with R ¹ and L in the above-mentioned general formula (1), respectively, and the preferred embodiments are also the same.
In the general formula (4), R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are synonymous with R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ in the general formula (3A) described above. And the preferred embodiment is the same.

The content of the repeating unit represented by the general formula (1) is preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, based on all the repeating units in the specific polymer. 10% by mass or more is particularly preferable. The upper limit is preferably 70% by mass or less, more preferably 60% by mass or less, and further preferably 50% by mass or less.
In the specific polymer, the repeating unit represented by the general formula (1) may be one type alone or a plurality of them in combination.

Next, the repeating unit represented by the general formula (2) will be described.

In the general formula (2), R ² and R ³ each independently represent a hydrogen atom or a substituent.
The substituent represented by ^R2 is not particularly limited, and examples thereof include a group exemplified by the substituent W described later.
The substituent represented by ^R2 is preferably a group represented by the following general formula (R1A).
General formula (R1A): * -L ¹ -R ¹⁴
In the general formula (R1A), L ¹ represents a single bond or an ester bond (-CO-O-).
R ¹⁴ represents a hydrogen atom or a substituent.
As the substituent represented by R ¹⁴ , an aryl group, an aralkyl group, an alkyl group, or a heteroaryl group which may have a substituent is preferable, and an aryl group which may have a substituent may be used. , A benzyl group or an alkyl group is more preferable, and an alkyl group which may have a substituent is further preferable. The alkyl group preferably does not have an aryl group as a substituent. The substituents that the aryl group, the aralkyl group, the alkyl group, and the heteroaryl group may have are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
* Represents the bond position.
When R ¹⁴ represents a hydrogen atom, L ¹ preferably represents an ester bond.
As R ¹⁴ , it is preferable to represent an aryl group, a benzyl group, an alkyl group, or a hydrogen atom which may have a substituent, and is an alkyl group which may have a substituent. It is more preferable to have it.

In the general formula (2), the type of the substituent represented by R ³ is not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
R ³ preferably represents an alkyl group which may have a hydrogen atom or a substituent, and may have a hydrogen atom or a substituent, because the effect of the present invention is more excellent. It is more preferable to represent a good alkyl group having 1 to 6 carbon atoms, further preferably to represent a hydrogen atom or a methyl group, and particularly preferably to represent a methyl group. In addition, examples of the substituent that the above-mentioned alkyl group may have include the groups exemplified by the substituent W described later.

In a preferred embodiment of the repeating unit represented by the general formula (2), R ² represents a group represented by the above general formula (R1A), and R ¹⁴ represents an aryl group, a benzyl group, or a group. , An alkyl group, or a hydrogen atom (preferably an alkyl group which may have a substituent), and R ³ represents a hydrogen atom or a methyl group (preferably a methyl group).
Further, as another preferable embodiment of the repeating unit represented by the general formula (2), there is also an embodiment in which the repeating unit is represented by the general formula (6).

In the general formula (6), R ³ and R ¹⁵ each independently represent a hydrogen atom or a substituent.
The R ³ in the general formula (6) has the same meaning as the R ³ in the general formula (2), and the preferred embodiment is also the same.

Examples of the substituent represented by R ¹⁵ include the groups exemplified by the substituent W described later. As the substituent represented by R ¹⁵ , an aryl group, an aralkyl group, an alkyl group, or a heteroaryl group which may have a substituent is preferable, and an aryl group which may have a substituent may be used. , A benzyl group, or an alkyl group is more preferable, and an alkyl group which may have a substituent is further preferable. The alkyl group preferably does not have an aryl group as a substituent.
The substituents that the aryl group, the aralkyl group, the alkyl group, and the heteroaryl group may have are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
The R ¹⁵ is preferably an aryl group, a benzyl group, an alkyl group, or an alkyl group which may have a substituent, and may have a substituent. It is more preferable to have it.

The content of the repeating unit represented by the general formula (2) is preferably 30% by mass or more, more preferably 50% by mass or more, based on all the repeating units in the specific polymer. The upper limit thereof is preferably 99.9% by mass or less, more preferably 99% by mass or less, further preferably 95% by mass or less, and particularly preferably 90% by mass or less.
In the specific polymer, the repeating unit represented by the general formula (2) may be one type alone or a plurality of them in combination.

As long as the effect of the present invention is not impaired, the specific polymer may contain a repeating unit represented by the above general formula (1) and other repeating units other than the repeating unit represented by the general formula (2). good.

The specific polymer can be synthesized according to a conventional method (for example, radical polymerization).
As the polystyrene conversion value by the GPC method, the weight average molecular weight of the specific polymer is preferably 1,000 to 100,000, more preferably 1,000 to 20,000, still more preferably 1,500 to 15,000, and 1 , 500-10,000 are particularly preferred.
The dispersity (molecular weight distribution) of the specific polymer is preferably 1 to 3, more preferably 1.2 to 3, and even more preferably 1.2 to 2.

In the composition, the lower limit of the content of the specific polymer is preferably 0.001% by mass or more, more preferably 0.1% by mass or more, and further preferably 1% by mass or more, based on the total solid content of the composition. preferable. The upper limit of the content of the specific polymer is preferably 40% by mass or less, more preferably 35% by mass or less, further preferably 25% by mass or less, and 20% by mass or less, based on the total solid content of the composition. Is particularly preferable, and 15% by mass or less is most preferable.
As used herein, the "solid content" of a composition means all components except the solvent. In addition, if it is a component other than a solvent, a liquid component is also regarded as a solid content.
Further, the specific polymer may be used alone or in combination of two or more.

(Substituent W)
The substituent W in the present specification will be described.
Examples of the substituent W include a halogen atom, an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, and an aryl. Group, heterocyclic group (may be called heterocyclic group), cyano group, hydroxy group, nitro group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy Group, aryloxycarbonyloxy group, amino group (including anilino group), ammonio group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino Group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, aryl or heterocycle Azo group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, phosphono group, silyl group, hydrazino group, ureido group, boronic acid group (-B (OH) ₂ ), and others. Examples of known substituents are mentioned.
Further, the substituent W may be further substituted with the substituent W. For example, the alkyl group may be substituted with a halogen atom.
The details of the substituent W are described in paragraph [0023] of JP-A-2007-234651.

(Aryl group, alkyl group, heteroaryl group that a specific polymer can have)
Hereinafter, one embodiment of an aryl group, an alkyl group, an aralkyl group, and a heteroaryl group that the specific polymer may have is shown.

Unless otherwise specified, the number of carbon atoms in the aryl group of the specific polymer is preferably 6 to 30, more preferably 6 to 18, and even more preferably 6. The aryl group may have a monocyclic structure or a condensed ring structure in which two or more rings are fused (condensed ring structure). Further, the aryl group may be substituted with a substituent (for example, the substituent W).
As the aryl group, for example, a phenyl group or a naphthyl group is preferable, and a phenyl group is more preferable.

Unless otherwise specified, the alkyl group of the specific polymer preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 4 carbon atoms. The alkyl group may be linear, branched, or cyclic. Further, the alkyl group may be substituted with a substituent (for example, substituent W).
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a 2-ethylhexyl group, a cyclohexyl group and the like. Can be mentioned.

The aralkyl group of the specific polymer is a group in which one of the hydrogen atoms of the alkyl group is substituted with an aryl group. The alkyl group portion of the aralkyl group of the specific polymer is the same as the preferred embodiment of the alkyl group of the specific polymer described above. Further, the aryl group portion of the aralkyl group of the specific polymer is the same as the preferred embodiment of the aryl group of the specific polymer described above.
Examples of the aralkyl group include a benzyl group and a phenethyl group.

Unless otherwise specified, the number of carbon atoms in the heteroaryl group (monovalent aromatic heterocyclic group) of the specific polymer is preferably 3 to 30, and more preferably 3 to 18. The heteroaryl group may be substituted with a substituent (for example, substituent W).
The heteroaryl group has a hetero atom in addition to a carbon atom and a hydrogen atom. Examples of the hetero atom include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, an oxygen atom, or a nitrogen atom is preferable.
Unless otherwise specified, the number of heteroatoms contained in the heteroaryl group is usually about 1 to 10, preferably 1 to 4, and more preferably 1 to 2.
Unless otherwise specified, the number of ring members of the heteroaryl group is preferably 3 to 8, more preferably 5 to 7, and even more preferably 5 to 6. The heteroaryl group may have a monocyclic structure or a condensed ring structure in which two or more rings are fused. In the case of a condensed ring structure, an aromatic hydrocarbon ring (for example, a benzene ring) having no heteroatom may be contained.

A specific example of the specific polymer is shown below.
In the following, the repeating unit (A), the repeating unit (B), and the repeating unit (C) are derived from the monomers shown in the columns of the repeating unit (A), the repeating unit (B), and the repeating unit (C). Intended to be a repeating unit. Further, "Me" in the polymer represents a methyl group, and "Et" represents an ethyl group.

〔Thermoplastic resin〕
The composition comprises a thermoplastic resin. The thermoplastic resin is a resin different from the above-mentioned specific polymer.
The thermoplastic resin is not particularly limited, and for example, polyamide resin, polyolefin resin, polyester resin, polyurethane resin, polyether ketone resin, polyether resin, polyimide resin, polyarylene sulfide resin, polyarylene ether resin, polycarbonate resin and the like. Can be mentioned.

The thermoplastic resin is preferably at least one selected from the group consisting of a polyamide resin and a polyolefin resin, and more preferably a polyamide resin.

The polyamide resin is a polymer having an acid amide bond (-CONH-) in the main chain. Examples of such polyamide resin include nylon 6 (also known as poly (caprolactum)), nylon 11 (also known as poly (11-aminoundecanoic acid)), nylon 12 (also known as poly (lauryllactam)) or poly (12-amino). Dodecanoic acid)), Nylon 6.6 (also known as poly (hexamethylene / adipamide)), Nylon 6.9 (also known as poly (hexamethylene / azelamide) or poly (hexamethylene / nonandiamide)), nylon 6.10 (also known as hexamethylene / nonandiamide). Also known as: Poly (hexamethylene sebacamide) or poly (hexanemethylene decandamide)), Nylon 6.12 (also known as poly (hexamethylene dodecanodiamide)), Nylon 4 (also known as poly (δ-butyrolactam)), Nylon 7 (also known as poly (7-aminohebutanoic acid) or poly (7-aminocapric acid)), nylon 8 (also known as poly (8-aminocapric acid) or poly (8-aminooctanoic acid)), nylon Examples thereof include 10, 6 (also known as poly (decamethylene / adipamide)) and partially aromatic nylon (PARNS).
Examples of commercially available products include "Nylon 6" manufactured by Sigma-Aldrich and "Daiamide" manufactured by Daicel Evonik.

Polyethylene resins include crystalline or amorphous polypropylene, polybutene-1, poly-4-methylpentene, low density or high density polyethylene, ethylene-propylene random, block, or graft copolymers, α-olefins and ethylene. Or a propylene copolymer, an ethylene- (meth) alkyl acid copolymer, an ethylene- (meth) acrylic acid copolymer, a poly (meth) acrylate, a binary of an olefin and an α, β-unsaturated carboxylic acid. It consists of a resin made of a metal ion neutralized product of a copolymer and a metal ion neutralized product of a ternary copolymer of olefin, α, β-unsaturated carboxylic acid and α, β-unsaturated carboxylic acid ester. Examples include resin. A resin composed of a metal ion neutralized product of a binary copolymer of an olefin and an α, β-unsaturated carboxylic acid, and an olefin and an α, β-unsaturated carboxylic acid and an α, β-unsaturated carboxylic acid. In a resin composed of a metal ion neutralized product of a ternary copolymer with an ester, the type and valence of the metal ion that neutralizes at least a part of the carboxy group are not particularly limited, and are, for example, sodium, potassium, and lithium. Monovalent metal ions such as; divalent metal ions such as magnesium, calcium, zinc, barium, and cadmium; trivalent metal ions such as aluminum; other ions such as tin and zirconium.

In the composition, the lower limit of the content of the thermoplastic resin is preferably 1% by mass or more, more preferably 10% by mass or more, still more preferably 30% by mass or more, more preferably 60% by mass, based on the total solid content of the composition. Mass% or more is particularly preferable. The upper limit of the content of the thermoplastic resin is preferably 99.999% by mass or less, more preferably 99.9% by mass or less, still more preferably 99% by mass or less, based on the total solid content of the composition. ..
Further, the thermoplastic resin may be used alone or in combination of two or more.

The combination of the specific polymer and the thermoplastic resin is preferably selected from the viewpoint of compatibility between the repeating unit represented by the general formula (2) contained in the specific polymer and the thermoplastic resin. As a combination of the repeating unit represented by the general formula (2) and the thermoplastic resin contained in the specific polymer, the compatibility between the two is excellent (in addition, a uniformly colored resin molded product can be obtained. (In terms of ease of use), the following aspects are preferable.
When the repeating unit represented by the general formula (2) is a repeating unit derived from (meth) acrylate, a preferred embodiment of the thermoplastic resin includes a polyolefin resin, a polyamide resin, a polyurethane resin, a polyester resin and the like. Can be mentioned.
When the repeating unit represented by the general formula (2) is a repeating unit derived from (meth) acrylic acid, a preferred embodiment of the thermoplastic resin includes a polyolefin resin, a polyamide resin and the like.
When the repeating unit represented by the general formula (2) is a repeating unit derived from styrene, a preferred embodiment of the thermoplastic resin includes a polyolefin resin and the like.

[Other additives]
The composition may contain additives other than the specific polymer and the thermoplastic resin.
The additive can be appropriately selected depending on the intended use, and is not particularly limited, and examples thereof include flame retardants, antioxidants, weather resistant agents, mold release agents, lubricants, plasticizers, fillers, and reinforcing materials.

〔Production method〕
The method for producing the above composition is not particularly limited, and examples thereof include a production method in which a specific polymer as a raw material component, a thermoplastic resin, and an arbitrary additive are premixed as necessary and then melt-kneaded. .. It is desirable to heat the melt kneading above the melting point of the thermoplastic resin. After melt kneading, it is preferably extruded into strands and then cut into granules such as pellets and chips.
As the melt-kneader, for example, a melt-kneader equipped with a heating mechanism such as a Banbury mixer, a mixing roll, a single-screw or twin-screw extruder, and a kneader can be used.

[Use]
The composition can be processed into a resin molded product having a desired shape by various melt molding such as injection molding, compression molding, composite, sheet, and pipe extrusion molding, pultrusion molding, blow molding, and transfer molding. The shape of the resin molded product is not particularly limited, and examples thereof include fibers, sheets, and films. The obtained resin molded product also has excellent sweat resistance.

Further, the above composition can also be used as a resin coloring composition (resin coloring masterbatch). Specifically, as a resin coloring composition (master batch for resin coloring), the above composition and a diluted resin which is a thermoplastic resin are mixed and used to obtain a resin molded product adjusted to a desired color. Can be formed. The obtained resin molded product also has excellent sweat resistance.
When the above composition is used as a resin coloring composition (resin coloring masterbatch), the content of the specific polymer in the composition is set to a relatively high concentration from the viewpoint of widening the color selection region. Is preferable. When used as a masterbatch for resin coloring, the content of the specific polymer in the composition is preferably 10 to 70% by mass with respect to the total solid content of the composition.
When the above composition is used as a resin coloring composition (resin coloring master batch), the blending ratio of the resin coloring composition (resin coloring master batch) and the diluted resin (thermoplastic resin) is not particularly limited. However, as one embodiment, the blending amount of the resin coloring composition is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the diluted resin (thermoplastic resin), preferably 3 to 10 parts by mass. More preferred.

The diluted resin is a thermoplastic resin as described above, and examples thereof include resins similar to the thermoplastic resin contained in the above composition, and among them, a polyamide resin or a polyolefin resin is preferable, and a polyamide resin is used. It is more preferable to have it.
The diluted resin to which the resin coloring composition is applied is preferably selected from the viewpoint of compatibility between the thermoplastic resin contained in the resin coloring composition and the diluted resin. The combination of the thermoplastic resin and the diluted resin contained in the resin coloring composition has excellent compatibility between the two (in addition, it is easy to obtain a uniformly colored resin molded product). Is preferable.
When the thermoplastic resin contained in the resin coloring composition is a polyamide resin, a preferred embodiment of the diluted resin is a polyamide resin, a polyurethane resin, a polyolefin resin (preferably poly (meth) acrylate), or the like. Can be mentioned. Of these, a polyamide resin is preferable.
When the thermoplastic resin contained in the resin coloring composition is a polyolefin resin, a preferred embodiment of the diluted resin is a polyolefin resin.

As a method of mixing the resin coloring composition and the diluted resin, a resin coloring composition (master batch for resin coloring), a thermoplastic resin which is a diluted resin, and an arbitrary additive component are premixed as necessary. Later, a manufacturing method of melt-kneading can be mentioned. The melt kneading is preferably heated to a temperature equal to or higher than the melting point of the thermoplastic resin in the resin coloring composition and the thermoplastic resin which is a diluted resin. After melt kneading, it is preferably extruded into strands and then cut into granules such as pellets and chips. As the melt kneader that can be used, the above-mentioned melt kneader can be used.

Colored resin compositions obtained by mixing a resin coloring composition and a diluted resin include various types such as injection molding, compression molding, extrusion molding of composites, sheets, and pipes, extraction molding, blow molding, and transfer molding. By melt molding, it can be processed into a resin molded product having a desired shape. The shape of the obtained resin molded product is not particularly limited, and examples thereof include fibers, sheets, and films.

[Polymer (polymer for resin coloring)]
The present invention also relates to polymers.
The polymer of the present invention is a polymer containing the repeating unit represented by the above-mentioned general formula (4) and the repeating unit represented by the above-mentioned general formula (2).
The polymer of the present invention corresponds to one aspect of the above-mentioned specific polymer, and the preferred embodiment thereof is the same as the preferred embodiment of the above-mentioned specific polymer.
The polymer of the present invention can stably function as a colorant for a resin even when used at a high concentration.

The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed as limiting by the examples shown below.

[Composite example]
[Example of synthesis of specific polymer]
<Synthesis Example 1 (Synthesis of Monomer M-1)>
The following monomer M-1 was synthesized with reference to JP-A-11-130817. The specific procedure is as follows.
In a solution obtained by dissolving Kumarin 7 (20 g, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) in N, N-dimethylacetamide (300 mL, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), tert-butoxypotassium (7.14 g, manufactured by Fujifilm Wako). (Made by Kojunyaku) was added, and the mixture was stirred at room temperature for 30 minutes under a nitrogen stream. Then, in the stirred solution, nitrobenzene (0.3 mL, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), sodium iodide (13.5 g, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 4-chloromethylstyrene (11.9 g). , Tokyo Kasei Kogyo Co., Ltd.) was added, and the mixture was stirred at 50 ° C. for 2 hours. The stirred solution was returned to room temperature, diluted with ethyl acetate, and water was added to separate the solutions. After the liquid separation, the organic phase was concentrated to precipitate a yellow solid, which was filtered and dried to obtain the monomer M-1.

<Synthesis Example 2 (Synthesis of Monomer M-2)>
Monomer M-2 shown below was synthesized by the same procedure as that for monomer M-1, except that allyl bromide (9.43 g, manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 4-chloromethylstyrene. did.

<Synthesis of polymer P-1>
The synthesized monomer M-1 (0.5 g) and methyl methacrylate (4.5 g, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) are dissolved in DMAc ((dimethylacetamide) 20 g, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) under a nitrogen stream. Was stirred at 85 ° C. for 3 hours. Next, V-601 (0.74 g, manufactured by Wako Pure Chemical Industries, Ltd.) was added to the stirred liquid, and the mixture was further stirred for 1 hour. Then, V-601 (0.32 g, manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was further stirred for 2 hours. After the stirring was completed, the temperature was returned to room temperature, water (900 mL) was added, reprecipitation was carried out, and the precipitate was filtered and dried to obtain polymer P-1. By GPC measurement, it was confirmed that the weight average molecular weight of the polymer P-1 was 4000.

<Synthesis of polymers P-2 to P-7>
Polymers P-2 to P-7 were synthesized according to the method for synthesizing polymer P-1, except that the monomer species shown in Table 1 were changed.
In Table 1, "MMA" means methyl methacrylate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), "MAA" means methacrylic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and "BzMA" means. Means benzyl methacrylate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
The compositions of the polymers P-1 to P-7 are shown in Table 1.
In Table 1, "mass%" described in the columns of "raw material monomer 1" to "raw material monomer 3" is derived from "raw material monomer 1" to "raw material monomer 3" with respect to all the repeating units in each polymer. The content of each repeating unit is intended.

[Preparation and evaluation of compositions of Examples and Comparative Examples]
[Preparation of Compositions of Examples and Comparative Examples]
<Example 1>
The polymer P-1 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-1 is 1% by mass with respect to the content of the polyamide resin, and the cylinder temperature: 270 ° C. , Screw rotation speed: Kneaded with a twin-screw extruder set to 100 rpm to prepare colored pellets.

<Example 2>
Colored pellets of Example 2 were prepared by the same method as in Example 1 except that the polymer P-2 was used instead of the polymer P-1.

<Example 3>
The colored pellets of Example 3 were prepared by the same method as in Example 1 except that the polymer P-3 was used instead of the polymer P-1.

<Example 4>
The colored pellets of Example 4 were prepared by the same method as in Example 1 except that the polymer P-4 was used instead of the polymer P-1.

<Example 5>
The polymer P-5 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-5 is 0.5% by mass with respect to the total amount of the polyamide resin, and the cylinder temperature: Colored pellets were prepared by kneading with a twin-screw extruder set at 270 ° C. and screw rotation speed: 100 rpm.

<Example 6>
The polymer P-6 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-6 is 0.2% by mass with respect to the content of the polyamide resin, and the cylinder temperature: Colored pellets were prepared by kneading with a twin-screw extruder set at 270 ° C. and screw rotation speed: 100 rpm.

<Example 7>
The colored pellets of Example 7 were prepared by the same method as in Example 1 except that the polymer P-7 was used instead of the polymer P-1.

<Example 8>
The polymer P-6 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-6 is 50% by mass with respect to the content of the polyamide resin, and the cylinder temperature: 270 ° C. , Screw rotation speed: Kneaded with a twin-screw extruder set to 100 rpm to prepare colored pellets.

<Example 9>
Polymer P-1 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-1 is 1% by mass with respect to the content of polyethylene resin, and the cylinder temperature is adjusted. Colored pellets were prepared by kneading with a twin-screw extruder set at 200 ° C. and screw rotation speed: 100 rpm.

<Example 10>
The colored pellets of Example 10 were prepared by the same method as in Example 9 except that the polymer P-2 was used instead of the polymer P-1.

<Example 11>
The colored pellets of Example 11 were prepared by the same method as in Example 9 except that the polymer P-3 was used instead of the polymer P-1.

<Example 12>
The colored pellets of Example 12 were prepared by the same method as in Example 9 except that the polymer P-4 was used instead of the polymer P-1.

<Example 13>
Polymer P-5 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-5 is 0.5% by mass with respect to the content of polyethylene resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm.

<Example 14>
Polymer P-6 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-6 is 0.2% by mass with respect to the content of polyethylene resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm.

<Example 15>
The colored pellets of Example 15 were prepared by the same method as in Example 9 except that the polymer P-7 was used instead of the polymer P-1.

<Example 16>
Polymer P-6 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-6 is 50% by mass with respect to the content of polyethylene resin, and the cylinder temperature is adjusted. Colored pellets were prepared by kneading with a twin-screw extruder set at 200 ° C. and screw rotation speed: 100 rpm.

<Example 17>
Polymer P-1 and polyester resin (trade name "polyethylene terephthalate", manufactured by Unitika Ltd.) are mixed so that the content of polymer P-1 is 1% by mass with respect to the content of polyester resin, and a cylinder is used. Colored pellets were prepared by kneading with a twin-screw extruder set at a temperature of 280 ° C. and a screw rotation speed of 100 rpm.

<Example 18>
The colored pellets of Example 18 were prepared by the same method as in Example 17 except that the polymer P-2 was used instead of the polymer P-1.

<Example 19>
The colored pellets of Example 19 were prepared by the same method as in Example 17 except that the polymer P-3 was used instead of the polymer P-1.

<Example 20>
The colored pellets of Example 20 were prepared by the same method as in Example 17 except that the polymer P-4 was used instead of the polymer P-1.

<Example 21>
Polymer P-5 and polyester resin (trade name "polyethylene terephthalate", manufactured by Unitika Ltd.) are mixed so that the content of polymer P-5 is 0.5% by mass with respect to the content of polyester resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 280 ° C. and a screw rotation speed of 100 rpm.

<Example 22>
The polymer P-6 and the polyester resin (trade name "polyethylene terephthalate", manufactured by Unitika Ltd.) are mixed so that the content of the polymer P-6 is 0.2% by mass with respect to the content of the polyester resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 280 ° C. and a screw rotation speed of 100 rpm.

<Example 23>
The colored pellets of Example 23 were prepared by the same method as in Example 17 except that the polymer P-7 was used instead of the polymer P-1.

<Comparative Example 1>
The comparative compound C-1 described later and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the comparative compound C-1 is 0.1% by mass with respect to the content of the polyamide resin. , Cylon temperature: 270 ° C., screw rotation speed: 100 rpm, kneaded with a twin-screw extruder to prepare colored pellets.

<Comparative Example 2>
The comparative compound C-2 described later and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the comparative compound C-2 is 0.1% by mass with respect to the content of the polyamide resin. , Cylon temperature: 270 ° C., screw rotation speed: 100 rpm, kneaded with a twin-screw extruder to prepare colored pellets.

<Comparative Example 3>
The comparative compound C-2 described later and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the comparative compound C-2 is 25% by mass with respect to the content of the polyamide resin, and the cylinder is used. Colored pellets were prepared by kneading with a twin-screw extruder set at a temperature of 270 ° C. and a screw rotation speed of 100 rpm.

<Comparative Example 4>
The comparative compound C-1 described later and the polyethylene resin (trade name “Sumicasen”, manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of the comparative compound C-1 is 0.1% by mass with respect to the content of the polyethylene resin. And kneaded with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets.

<Comparative Example 5>
The comparative compound C-2 described later and the polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of the comparative compound C-2 is 0.1% by mass with respect to the content of the polyethylene resin. And kneaded with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets.

<Comparative Example 6>
The comparative compound C-2, which will be described later, and a polyethylene resin (trade name “Sumikasen”, manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of the comparative compound C-2 is 25% by mass with respect to the content of the polyethylene resin. Then, the mixture was kneaded with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets.

[Evaluation of Compositions of Examples and Comparative Examples]
The following evaluations (light resistance evaluation, sweat resistance evaluation) were carried out for each composition of Examples and Comparative Examples. In the evaluation, each composition (colored pellet) of Examples and Comparative Examples was heated and formed to prepare a resin film having a thickness of 2 mm, which was used as an evaluation sample.
<Light resistance evaluation>
A light resistance test was carried out on each of the resin films of Examples and Comparative Examples. Specifically, after exposing the resin film for 45 hours using a xenon lamp (trade name "BXDN-500N", manufactured by Nowdata), the degree of fading is visually observed and evaluated based on the following evaluation criteria. Carried out.
(Light resistance evaluation: evaluation criteria)
"A": Low degree of fading "B": Medium degree of fading "C": Large degree of fading The results are shown in Table 2.

<Sweat resistance evaluation>
A sweat resistance test was carried out on each of the resin films of Examples and Comparative Examples. Specifically, after applying a cloth soaked in artificial sweat (manufactured by Kishida Chemical Co., Ltd.) for 30 minutes to a resin film and pressurizing it at 40 ° C. for 4 hours, visually observe the degree of fading and use the following evaluation criteria. The evaluation was carried out based on.
(Sweat resistance evaluation: evaluation criteria)
"A": The degree of fading is small "B": The degree of fading is large The results are shown in Table 2.

As shown in Table 2, it is clear that the compositions of Examples are excellent in light resistance and sweat resistance.
Further, from the results of Examples 1 to 23, it was confirmed that when the repeating unit represented by the general formula (1) in the specific polymer is the repeating unit represented by the general formula (5), the light resistance is more excellent. (Results of Examples 7, 15, 23, etc.).
Further, from the results of Examples 1 to 23, when the repeating unit represented by the general formula (2) in the specific polymer satisfies the following condition 1 or condition 2 (preferably, the condition 2 is satisfied), the light resistance is reduced. It was confirmed that the sex tends to be better (results of Examples 10, 11, 18 to 20, etc.).
Condition 1: In the repeating unit represented by the general formula (2) in the specific polymer, R ² represents a group represented by the above general formula (R1A), and R ¹⁴ has a substituent. Represents a optionally alkyl group, where R ³ represents a hydrogen atom or a methyl group.
Condition 2: The content of the repeating unit satisfying the condition 1 satisfies 50% by mass or more with respect to all the repeating units in the specific polymer.
On the other hand, the compositions of Comparative Examples did not meet the desired requirements.

[Example 24: Performance evaluation as a resin coloring composition]
The colored pellets prepared in Example 8 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) were prepared so that the content of the colored pellets prepared in Example 8 was 4% by mass with respect to the content of the polyamide resin. The mixture was mixed and kneaded by a twin-screw extruder set at a cylinder temperature of 270 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets. Next, the obtained colored pellets were heated and formed to prepare a resin film having a thickness of 2 mm. When the prepared resin film was visually observed, it was confirmed that the polyamide resin was uniformly colored. Moreover, when the above-mentioned light resistance evaluation and sweat resistance evaluation were carried out on the produced resin film, it was confirmed that the degree of fading was small (“A” evaluation).

Claims

A polymer containing a repeating unit represented by the following general formula (1) and a repeating unit represented by the following general formula (2),
A composition comprising a thermoplastic resin.

In the general formula (1), R 1 represents a hydrogen atom or a substituent. L represents a divalent linking group. X 1 represents a residue derived from the compound represented by the following general formula (3).
In the general formula (2), R 2 and R 3 each independently represent a hydrogen atom or a substituent.

In the general formula (3), X 2 represents a coumarin ring group which may have a substituent. Y represents an oxygen atom, a sulfur atom, or NR 8 . R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or substituent.
However, at least one of R4 , R5, R6, R7 , and R8 in the general formula ( 3 ) represents a hydrogen atom, and one of the hydrogen atoms is removed, so that the general formula is used. Residues derived from the compound represented by (3) are formed.
The composition according to claim 1, wherein the repeating unit represented by the general formula (1) is a repeating unit represented by the following general formula (4).

In the general formula (4), R 1 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 , R 11 , R 12 and R 13 each independently represent a hydrogen atom or a substituent. .. L represents a divalent linking group.
The composition according to claim 1 or 2, wherein in the general formula (2), R 2 represents a group represented by the following general formula (R1A), and R 3 represents a hydrogen atom or a methyl group.
General formula (R1A): * -L 1 -R 14
In the general formula (R1A), L 1 represents a single bond or an ester bond. R 14 represents an aryl group, a benzyl group, an alkyl group, or a hydrogen atom which may have a substituent. * Represents the bond position.
The repeating unit represented by the general formula (1) is the repeating unit represented by the following general formula (5), and the repeating unit represented by the general formula (2) is the following general formula (6). The composition according to claim 1 or 2, which is a repeating unit represented.

In the general formula (6), R 3 and R 15 each independently represent a hydrogen atom or a substituent.
In the general formula (6), R 3 represents a hydrogen atom or a methyl group, and R 15 represents an aryl group, a benzyl group, an alkyl group, or a hydrogen atom which may have a substituent. , The composition according to claim 4.
The composition according to any one of claims 1 to 5, wherein the thermoplastic resin is at least one selected from the group consisting of a polyamide resin and a polyolefin resin.
The polymer is
The weight average molecular weight is 1,000 to 100,000, and
The item according to any one of claims 1 to 6, wherein the content of the repeating unit represented by the general formula (1) is 0.1 to 50% by mass with respect to all the repeating units in the polymer. Composition.
A resin coloring composition comprising the composition according to any one of claims 1 to 7.
A polymer comprising a repeating unit represented by the following general formula (4) and a repeating unit represented by the following general formula (2).

In the general formula (4), R 1 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 , R 11 , R 12 and R 13 each independently represent a hydrogen atom or a substituent. .. L represents a divalent linking group.
In the general formula (2), R 2 and R 3 each independently represent a hydrogen atom or a substituent.
The repeating unit represented by the general formula (4) is the repeating unit represented by the following general formula (5), and the repeating unit represented by the general formula (2) is the following general formula (6). The polymer according to claim 9, which is a repeating unit represented.

In the general formula (6), R 3 and R 15 each independently represent a hydrogen atom or a substituent.
In the general formula (6), R 3 represents a hydrogen atom or a methyl group, and R 15 represents an aryl group, a benzyl group, an alkyl group, or a hydrogen atom which may have a substituent. , The polymer according to claim 10.
The weight average molecular weight is 1,000 to 100,000, and
The item according to any one of claims 9 to 11, wherein the content of the repeating unit represented by the general formula (4) is 0.1 to 50% by mass with respect to all the repeating units in the polymer. polymer.