Compound

Abstract

The present invention provides a compound which is capable of forming a cured film.　The present invention provides a compound which has a furan structure and two or more (meth)acryloyl groups in a molecule.

Description

compound

[0001] The present invention relates to compounds.

[0002] Various methods for forming a cured film have been studied. For example, Patent Document 1 discloses a method for producing a laminate that forms a cured film having excellent matte properties.

[0003] JP 2023-108836 A

[0004] However, there is also a need to develop a method for forming a cured film using other raw materials.

[0005] The present invention has been made in view of the above circumstances, and provides a compound capable of forming a cured film.

[0006] According to the present invention, there is provided a compound having a furan structure and two or more (meth)acryloyl groups in the molecule.

[0007] Various embodiments of the present invention are exemplified below. The embodiments shown below can be combined with each other. [1] A compound having a furan structure and two or more (meth)acryloyl groups in the molecule. [2] The compound according to [1], in which at least two of the (meth)acryloyl groups are located at the terminals of the molecule. [3] The compound according to [2], which is represented by the following formula (1): (In formula (1), X １ , X ２respectively represent an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms which may have a substituent, an arylene group having 6 to 18 carbon atoms which may have a substituent, a cyclo ... X is selected from an alkylenearylene group having a prime number of 7 to 30, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, and Y １ , Y ２ , Y ３ , Y ４ are O or NR ３ and R １ , R ２ , R ３ are H or CH ３ or CH ２ CH ３ and n is a natural number from 1 to 50. [4] The compound according to [2], having a structure represented by the following formula (2): (In formula (2), X ３ , X ４are each selected from an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms which may have a substituent, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, the alkylene group is selected from Y in which at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom. ５ and Y ６ are O or NR ６ and R ４ , R ５ , R ６ are H or CH ３ or CH ２ CH ３ [5] The compound according to [2], having a structure represented by the following formula (1-2): (In formula (1-2), X ５ , X ６respectively represent an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, and X is selected from a cycloalkylene group having 3 or more carbon atoms, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, and Y ７ and Y ８ are O or NR ９ and R ７ , R ８ , R ９ are H or CH ３ or CH ２ CH ３ and m is a natural number from 1 to 50. [6] The compound according to [2], having a structure represented by the following formula (2-2): (In formula (2-2), X ７ , X ８respectively represent an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, and X is selected from a cycloalkylene group having 3 or more carbon atoms, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, R １０ , R １１ are H or CH ３ or CH ２ CH ３ is)

[0008] The compound according to the present invention can form a cured film.

[0009] FIG. 1 shows the structure of Compound I according to Example 1. １ 1 H-NMR spectrum of Compound I of Example 1.

[0010] The present invention will be described in detail below by illustrating embodiments of the present invention. The present invention is not limited by these descriptions. The features of the embodiments of the present invention described below can be combined with each other. Furthermore, each feature can be an invention independently.

[0011] 1. Compound The compound according to the present invention has a furan structure and two or more (meth)acryloyl groups in the molecule. The compound according to the present invention is capable of forming a hard cured film (for example, having a pencil hardness of B or higher). The compound according to one embodiment of the present invention is obtained from renewable raw materials and is capable of forming a cured film with a certain degree of hardness. Furthermore, the compound according to one embodiment of the present invention has the above structure, making it possible to form a cured film that is hard and durable to a certain degree and that is rapidly decomposable in a specific environment and / or after a specific period of time.

[0012] The compound according to the present invention may be a monomer having a furan structure and two or more (meth)acryloyl groups in the molecule, or a polymer having two or more specific repeating units. First, a common aspect when the compound is a monomer and when it is a polymer will be described.

[0013] The compound according to the present invention contains a furan structure. The term "containing a furan structure" means that the compound has a structure derived from furan and a furan substitution product, which are five-membered ring structures shown below, and that the compound has a group obtained by removing any hydrogen atom from the following structure and / or a furan substitution product.

[0014]

[0015] The compound according to the present invention may have one or more furan structures in the molecule, and may also have two or more furan structures.

[0016] The compound according to the present invention has two or more (meth)acryloyl groups, and may have three or more (meth)acryloyl groups. Preferably, at least two of the (meth)acryloyl groups are located at molecular terminals. All of the (meth)acryloyl groups may be located at terminals. The compound according to the present invention may also have terminals other than (meth)acryloyl groups. In a compound according to one embodiment of the present invention, at least two of the molecular terminals of the compound are (meth)acryloyl group terminals, and preferably more than half of the molecular terminals of the compound are (meth)acryloyl group terminals. When the number of molecular terminals of the compound is taken as 100, the number of (meth)acryloyl group terminals may be, for example, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100, and may be within a range between any two of the values ​​exemplified here.

[0017] A compound according to one embodiment of the present invention can have a structure represented by the following formula (1), (2), (1-2), or (2-2): (In formula (1), X １ , X ２are each selected from an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms which may have a substituent, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X comprises an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, Y １ , Y ２ , Y ３ , Y ４ are O or NR ３ and R １ , R ２ , R ３ are H or CH ３ or CH ２ CH ３ and n is a natural number from 1 to 50.

[0018] (In formula (2), X ３ , X ４respectively represent an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, and X is selected from a cycloalkylene group having 3 or more carbon atoms, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, and Y ５ and Y ６ are O or NR ６ and R ４ , R ５ , R ６ are H or CH ３ or CH ２ CH ３ is)

[0019] (In formula (1-2), X ５ , X ６respectively represent an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, and X is selected from a cycloalkylene group having 3 or more carbon atoms, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, and Y ７ and Y ８ are O or NR ９ and R ７ , R ８ , R ９ are H or CH ３ or CH ２ CH ３ and m is a natural number from 1 to 50.

[0020] (In formula (2-2), X ７ , X ８respectively represent an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, and X is selected from a cycloalkylene group having 3 or more carbon atoms, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, R １０ , R １１ are H or CH ３ or CH ２ CH ３ is)

[0021] In formula (1), formula (2), formula (1-2), and formula (2-2), X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８are each selected from an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylenecycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylenealkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent, an arylenealkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom.

[0022] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ can be an alkylene group having 2 or more carbon atoms which may have a substituent. The number of carbon atoms of the alkylene group is, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, and may be within a range between any two of the numbers exemplified here. Examples of alkylene groups having 2 or more carbon atoms include an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, and a dodecylene group.

[0023] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８can be an alkenylene group having 2 or more carbon atoms which may have a substituent. The number of carbon atoms of the alkenylene group is, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, and may be within a range between any two of the numbers exemplified here. Examples of alkenylene groups having 2 or more carbon atoms include ethenylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, and decenylene groups.

[0024] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ can be an alkynylene group having 2 or more carbon atoms which may have a substituent. The number of carbon atoms of the alkynylene group is, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, and may be within a range between any two of the numbers exemplified here. Examples of alkynylene groups having 2 or more carbon atoms include an ethynylene group, a propynylene group, a butynylene group, and a pentynylene group.

[0025] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８can be a cycloalkylene group having 3 or more carbon atoms which may have a substituent. The number of carbon atoms of the cycloalkylene group is, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, and may be within a range between any two of the numbers exemplified here. Examples of cycloalkylene groups having 3 or more carbon atoms include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, and a cyclononylene group. A cyclopentylene group, a cyclohexylene group, or a cycloheptylene group is preferred, and a cyclohexyl group is more preferred. As the cyclohexyl group, a 1,4-cyclohexyl group or a 1,2-cyclohexyl group is preferred.

[0026] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ can be an alkylenecycloalkylene group having 4 to 30 carbon atoms, which may have a substituent. The alkylenecycloalkylene group refers to a group containing both an alkylene group and a cycloalkylene group, with the cycloalkylene group being located on the main skeleton side. The number of carbon atoms in the alkylenecycloalkylene group is, for example, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30, and may be within a range between any two of the values ​​exemplified here. Examples of alkylenecycloalkylene groups having 4 or more carbon atoms include a methylenecyclohexylene group and an ethylenecyclohexylene group.

[0027] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８can be a cycloalkylene alkylene group having 4 to 30 carbon atoms, which may have a substituent. The cycloalkylene alkylene group refers to a group containing both a cycloalkylene group and an alkylene group, with the alkylene group being located on the main skeleton side. The number of carbon atoms in the cycloalkylene alkylene group is, for example, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30, and may be within a range between any two of the values ​​exemplified here. Examples of cycloalkylene alkylene groups having 4 to 30 carbon atoms include a cyclohexylenemethylene group and a cyclohexylene group.

[0028] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ can be an arylene group having 6 to 18 carbon atoms which may have a substituent. The number of carbon atoms of the arylene group is, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, and may be within a range between any two of the numbers exemplified here. Examples of the arylene group having 6 to 18 carbon atoms include an anthracenyl group, a naphthylene group, and an anthracenyl group.

[0029] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８can be an alkylenearylene group having 7 to 30 carbon atoms which may have a substituent. The alkylenearylene group refers to a group which contains both an alkylene group and an arylene group, with the arylene group being located on the main skeleton side. The number of carbon atoms in the alkylenearylene group is, for example, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30, and may be within a range between any two of the values ​​exemplified here. Examples of alkylenearylene groups having 7 to 30 carbon atoms include a methylenephenylene group, an ethylenephenylene group, a methylenenaphthylene group, and an ethylenenaphthylene group.

[0030] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ can be an arylene alkylene group having 7 to 30 carbon atoms which may have a substituent. The arylene alkylene group refers to a group which contains both an arylene group and an alkylene group, with the alkylene group being located on the main skeleton side. The number of carbon atoms in the arylene alkylene group is, for example, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30, and may be within a range between any two of the values ​​exemplified here. Examples of the arylene alkylene group having 7 to 30 carbon atoms include a phenylene methylene group, a phenylene ethylene group, a naphthylene methylene group, and a naphthylene ethylene group.

[0031] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８can be a divalent three-, four-, five-, or six-membered ring containing a heteroatom, which may have a substituent. The divalent three-, four-, five-, and six-membered ring containing a heteroatom can have at least one heteroatom selected from N, O, and S, and preferably contains O. The divalent three-, four-, five-, and six-membered ring containing a heteroatom preferably has at least one O, and can have one, two, or three O. The heterocycle is preferably a divalent five- or six-membered ring, and more preferably a divalent five-membered ring. The divalent three-, four-, five-, and six-membered ring containing a heteroatom preferably contains a skeleton selected from pyrrole, pyridine, thiophene, furan, 2H-pyran, 4H-pyran, oxazole, isoxazole, morpholine, and oxazoline, and preferably contains a furan structure. The furan structure is as described below. X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ preferably has a group in which any two hydrogen atoms have been removed from furan and / or a furan substituent.

[0032] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ is more preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained in these structures is substituted with a divalent heteroatom (for example, oxygen). １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８may be the same or different.

[0033] X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ When "X" contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom. １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ "When X contains an alkylene group" means １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ is an alkylene group, and X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ is a cycloalkylene group, an alkylenearylene group, or an alkylenearylene group in which X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ The case where X contains an alkylene group as a part thereof is also included. １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８The alkylene group in X may be substituted with a divalent heteroatom, for example, with an oxygen atom. That is, it may have an ether bond. １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ The alkylene group in X may have at least one ether bond, may have one or two ether bonds, or may have one ether group. １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ may not contain any substituents. １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ , X ８ When contains a substituent, examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a hydroxyl group.

[0034] In formula (1), formula (2), formula (1-2), and formula (2-2), Y １ , Y ２ , Y ３ , Y ４ , Y ５ , Y ６ , Y ７ , Y ８ are O or NR ３ And it can be O. Y １ , Y ２ , Y ３ , Y ４ , Y ５ , Y ６ , Y ７ , Y ８ may be the same or different.

[0035] In the formula (1), the formula (2), the formula (1-2), and the formula (2-2), R１ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ are H or CH ３ or CH ２ CH ３ and can be expressed as H. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ may be the same or different.

[0036] In formula (1), n ​​is a natural number from 1 to 50. In formula (1-2), m is a natural number from 1 to 50.

[0037] The compound according to the present invention can be a monomer or a polymer. Hereinafter, the cases where the compound is a monomer and the case where the compound is a polymer will be described in detail.

[0038] 1.1 Monomer When the compound is a monomer, the (number average) molecular weight can be 300 or more. When the compound is a monomer, the molecular weight can be, for example, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, or 2000, or can be within a range between any two of the values ​​exemplified here. The number average molecular weight of the compound can be determined by measurement using GPC (gel permeation chromatography) under the following conditions. Measurement equipment: HLC-8320GPC (manufactured by Tosoh Corporation) GPC column configuration: the following four columns in series (all manufactured by Tosoh Corporation) (1) TSKgel HxL-H (guard column) (2) TSKgel GMHxL (3) TSKgel GMHxL (4) TSKgel G2500HxL Flow rate: 1.0 mL / min Column temperature: 40°C Sample concentration: 1.5% (w / v) (diluted with tetrahydrofuran) Mobile phase solvent: tetrahydrofuran Standard polystyrene equivalent

[0039] When the compound is a monomer, the compound according to one embodiment of the present invention may have two or four molecular terminals, preferably at least two or more (meth)acryloyl group terminals, and may have three or more or four (meth)acryloyl group terminals.

[0040] When the compound is a monomer, it can be any of the following: - Represented by formula (1) where n = 1 - Has a structure represented by formula (2) - Represented by formula (1-2) where m = 1 - Has a structure represented by formula (2-1)

[0041] When the compound is represented by formula (1) where n=1, that is, formula (4), X in formula (4) １ , X ２ Specific examples of X are as described above. When the compound is represented by formula (4), X １ , X ２is preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained in these groups is substituted with a divalent heteroatom (for example, oxygen), and more preferably an alkenylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained therein is substituted with a divalent heteroatom (for example, oxygen). X １ , X ２ When the compound is represented by formula (4), Y １ , Y ２ , Y ３ , Y ４ Specific examples of are as described above. When the compound is represented by formula (4), Y １ , Y ２ , Y ３ , Y ４ More preferably, Y is O. １ , Y ２ , Y ３ , Y ４ may be the same or different. When the compound is represented by formula (4), R １ , R ２ , R ３ Specific examples of R are as described above. When the compound is represented by formula (4), R １ , R ２ , R ３ is more preferably H. When the compound is represented by formula (4), the compound has two (meth)acryloyl groups at its terminals. １ , R ２ , R ３ may be the same or different.

[0042]

[0043] When the compound is represented by formula (1-2) where m=1, that is, formula (4-2), X in formula (4-2) ５ , X ６Specific examples of X are as described above. When the compound is represented by formula (4), X ５ , X ６ is preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained in these groups is substituted with a divalent heteroatom (for example, oxygen), and more preferably an alkenylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained therein is substituted with a divalent heteroatom (for example, oxygen). X ５ , X ６ When the compound is represented by formula (4-2), Y ７ , Y ８ Specific examples of are as described above. When the compound is represented by formula (4), Y ７ , Y ８ More preferably, Y is O. ７ , Y ８ may be the same or different. When the compound is represented by formula (4-2), R ７ , R ８ , R ９ Specific examples of are as described above. When the compound is represented by formula (4-2), R ７ , R ８ , R ９ is more preferably H. When the compound is represented by formula (4-2), the compound has two (meth)acryloyl groups at its terminals. ７ , R ８ , R ９ may be the same or different.

[0044]

[0045] When the compound has a structure represented by formula (2), X in formula (2) ３ , X ４ Specific examples of X are as described above. ３ , X４ is preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, and a cycloalkylene group having 2 or more carbon atoms which may have a substituent, more preferably an alkenylene group having 2 or more carbon atoms which may have a substituent, and even more preferably an alkylene group having 6 or more carbon atoms which may have a substituent. ３ , X ４ When the compound has a structure represented by formula (2), Y in formula (2) may be the same or different. ５ , Y ６ Specific examples of Y are as described above. When the compound has a structure represented by formula (2), ５ , Y ６ More preferably, Y is O. ５ , Y ６ When the compound has a structure represented by formula (2), R ４ , R ５ , R ６ Specific examples of R are as described above. When the compound has a structure represented by formula (2), R ４ , R ５ , R ６ More preferably, R is H. ４ , R ５ , R ６ may be the same or different.

[0046] When the compound has a structure represented by formula (2), the compound can have a structure represented by formula (5) or formula (6).

[0047]

[0048]

[0049] When the compound has a structure represented by formula (5) or formula (6), X in formula (5) or formula (6) １３ , X １４ , X ２３ , X ２４ , X ３３ , X ３４A specific example of X ３ , X ４ When the compound has a structure represented by formula (5) or formula (6), X １３ , X １４ , X ２３ , X ２４ , X ３３ , X ３４ is preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained in these structures is substituted with a divalent heteroatom (for example, oxygen), more preferably selected from an alkenylene group having 2 or more carbon atoms which may have a substituent and structures in which at least one carbon atom in the alkylene group contained therein is substituted with a divalent heteroatom (for example, oxygen), and even more preferably selected from an alkylene group of an alkylene group having 6 or more carbon atoms which may have a substituent and structures in which at least one carbon atom in the alkylene group contained therein is substituted with a divalent heteroatom (for example, oxygen). １３ , X １４ , X ２３ , X ２４ , X ３３ , X ３４ When the compound has a structure represented by formula (5) or formula (6), Y in formula (5) or formula (6) may be the same or different. １５ , Y １６ , Y ２５ , Y ２６ , Y ３５ , Y ３６ A specific example of Y ５ , Y ６ When the compound has a structure represented by formula (5) or (6), Y １５ , Y １６ , Y ２５ , Y ２６ , Y ３５ , Y ３６ More preferably, Y is O. １５ , Y １６, Y ２５ , Y ２６ , Y ３５ , Y ３６ When the compound has a structure represented by formula (5) or formula (6), R in formula (5) or formula (6) may be the same or different. １４ , R １５ , R １６ , R ２４ , R ２５ , R ２６ , R ３４ , R ３５ , R ３６ A specific example of R ４ , R ５ , R ６ When the compound has a structure represented by formula (5) or (6), R １４ , R １５ , R １６ , R ２４ , R ２５ , R ２６ , R ３４ , R ３５ , R ３６ More preferably, R is H. １４ , R １５ , R １６ , R ２４ , R ２５ , R ２６ , R ３４ , R ３５ , R ３６ may be the same or different. When the compound is represented by formula (5), the compound has four (meth)acryloyl group terminals. When the compound is represented by formula (6), the compound has two (meth)acryloyl group terminals.

[0050] When the compound has a structure represented by formula (2-2), the compound can have a structure represented by formula (5-2) or formula (6-2).

[0051]

[0052]

[0053] When the compound has a structure represented by formula (5-2) or formula (6-2), X in formula (5-2) or formula (6-2) ４７ , X４８ , X ５７ , X ５８ , X ６７ , X ６８ A specific example of X ７ , X ８ When the compound has a structure represented by formula (5-2) or formula (6-2), X ４７ , X ４８ , X ５７ , X ５８ , X ６７ , X ６８ is preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and structures in which at least one carbon atom in the alkylene group contained in these structures is substituted with a divalent heteroatom (for example, oxygen), more preferably selected from an alkenylene group having 2 or more carbon atoms which may have a substituent and structures in which at least one carbon atom in the alkylene group contained therein is substituted with a divalent heteroatom (for example, oxygen), and even more preferably selected from an alkylene group of an alkylene group having 6 or more carbon atoms which may have a substituent and structures in which at least one carbon atom in the alkylene group contained therein is substituted with a divalent heteroatom (for example, oxygen). ４７ , X ４８ , X ５７ , X ５８ , X ６７ , X ６８ When the compound has a structure represented by formula (5-2) or formula (6-2), R in formula (5) or formula (6) ４１０ , R ４１１ , R ５１０ , R ５１１ , R ６１０ , R ６１１ A specific example of R １０ , R １１ When the compound has a structure represented by formula (5-2) or formula (6-2), R ４１０ , R ４１１ , R ５１０ , R５１１ , R ６１０ , R ６１１ More preferably, R is H. ４１０ , R ４１１ , R ５１０ , R ５１１ , R ６１０ , R ６１１ may be the same or different. When the compound is represented by formula (5-2), the compound has four (meth)acryloyl group terminals. When the compound is represented by formula (6-2), the compound has two (meth)acryloyl group terminals.

[0054] 1.2 Polymer When the compound is a polymer, the (number average) molecular weight of the compound can be 3 million to 50 million. The number average molecular weight of the polymer is, for example, 300, 500, 1,000, 5,000, 10,000, 20,000, 40,000, 50,000, 100,000, 500,000, 1 million, 5 million, 10 million, or 50 million, and may be within a range between any two of the values ​​exemplified here. The number average molecular weight of the polymer can be determined by the same method as described above.

[0055] A polymer according to one embodiment of the present invention can be a polymer having a structure represented by formula (1) or formula (1-2) in which n is 2 or more. When the compound is represented by formula (1) or formula (1-2) in which n is 2 or more, X in formula (1) or formula (1-2) １ , X ２ , X ５ , X ６ Specific examples of X are as described above. When the compound is represented by formula (1) in which n is 2 or more, １ , X ２ , X ５ , X ６ is preferably selected from an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, and a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and is more preferably an alkenylene group having 2 or more carbon atoms which may have a substituent. In addition, it is more preferable that the alkylene group has at least one carbon atom contained in the alkylene group substituted with a divalent heteroatom (for example, an oxygen atom). That is, X１ , X ２ , X ５ , X ６ is preferably selected from an alkylene group having 2 or more carbon atoms, an alkenylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 2 or more carbon atoms which may have a substituent, and a structure in which at least one carbon atom in the alkylene group contained in these structures is substituted with a divalent heteroatom (for example, oxygen); more preferably selected from an alkenylene group having 2 or more carbon atoms which may have a substituent, and a structure in which at least one carbon atom in the alkylene group contained in this structure is substituted with a divalent heteroatom (for example, oxygen); and more preferably selected from an alkenylene group having 6 or more carbon atoms which may have a substituent, and a structure in which at least one carbon atom in the alkylene group contained in this structure is substituted with a divalent heteroatom (for example, oxygen). When the compound is represented by formula (1) or formula (1-2) in which n is 2 or more, Y １ , Y ２ , Y ３ , Y ４ , Y ７ , Y ８ When the compound is represented by formula (1) in which n is 2 or more, Y １ , Y ２ , Y ３ , Y ４ , Y ７ , Y ８ is more preferably O. When the compound is represented by formula (1) or formula (1-2) in which n is 2 or more, R in formula (1) １ , R ２ , R ３ , R ７ , R ８ , R ９ Specific examples of R are as described above. When the compound is represented by formula (1) in which n is 2 or more, R １ , R ２ , R ３ , R ７ , R ８ , R ９is more preferably H. When the compound is represented by formula (1) or formula (1-2) in which n is 2 or more, the compound has two (meth)acryloyl group terminals.

[0056] 1.3 Characteristics of the Compound The compound according to one embodiment of the present invention can be used to produce a cured film. The cured film (cured product) according to one embodiment of the present invention is a polymer of the compound according to one embodiment of the present invention, and the polymer may be linear or network-like.

[0057] For example, a composition containing a compound according to one embodiment of the present invention, a photoinitiator, a photocuring agent other than the compound according to one embodiment of the present invention, and optionally other monomers can be prepared, and a molded body can be formed from the composition, followed by irradiating the molded body with light. When the compound according to one embodiment of the present invention is prepared as a composition described in the Examples and a cured film is produced using the method described in the Examples, the cured film preferably has a pencil hardness of B or greater. Furthermore, when the gel fraction of the cured film is determined using the method described in the Examples, the gel fraction is preferably 90% or greater, more preferably 95% or greater. The gel fraction may be, for example, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or 100%, and may be within a range between any two of the values ​​exemplified herein.

[0058] The compounds (monomers, polymers, and cured products thereof) according to one embodiment of the present invention are preferably biodegradable. Biodegradability can be evaluated, for example, by a BOD (Biochemical Oxygen Demand) test using seawater. Biodegradability can be evaluated by a BOD (Biochemical Oxygen Demand) test using seawater actually collected from nearby waters. Specifically, the evaluation can be performed by the following method. 30 mg of the monomer, polymer, and cured product thereof to be evaluated are placed in a 575 ml glass bottle (total volume including the cap: 610 ml), and 250 ml of seawater is added. The bottle is stirred thoroughly, then the BOD measurement cap is attached, and the bottle is placed in a thermostatic chamber set to 20°C. Stirring is started, and measurement is started once the temperature reaches 20°C. Similarly, two samples were prepared in the same bottle: 250 ml of seawater only (blank) and 250 ml of seawater with 30 mg of P3HB (polyhydroxybutyric acid, standard substance). Measurements were similarly started when the temperature reached 20°C. Oxygen consumption was measured from the change in internal pressure of the bottle once a day to determine the marine biodegradation rate. The compound according to one embodiment of the present invention, by having the above structure, can form a cured film that is relatively hard and durable, and that is rapidly degradable in a specific environment and / or after a specific period of time.

[0059] 2. Method for Producing Compounds The method for producing the compounds according to the present invention is not particularly limited. A method for producing a compound having a structure represented by formula (4) according to one embodiment of the present invention can include a step of reacting 2,5-furandicarbonyl dichloride and a hydroxyalkyl acrylate to obtain a compound having a structure represented by formula (4). As an example, a method for producing a compound having a structure represented by formula (4) according to one embodiment of the present invention can include a step of adding 2,5-furandicarbonyl dichloride dropwise to a solvent containing a hydroxyalkyl acrylate and pyridine, followed by stirring, to obtain a compound having a structure represented by formula (4). The reaction temperature can be 10 to 50°C, and the reaction time can be 2 to 14 hours. The method can also include a washing step of removing pyridine from the obtained product, a step of removing NaHCO ３Addition of aqueous solution, extraction with solvent such as ethyl acetate, washing with purified water, Mg ２ SO ４ Alternatively, a dehydration operation by, for example, heating and / or removing the solvent under reduced pressure, or a distillation operation may be carried out.

[0060] A method for producing a compound having a structure represented by formula (1) wherein n is 2 or more according to one embodiment of the present invention may include a step of reacting dimethyl 2,5-furandicarboxylate with a diol (e.g., dialkylene glycol) to obtain a precursor represented by formula (7), and a step of reacting the precursor represented by formula (7) with a (meth)acrylate having a halogen atom to obtain a compound having a structure represented by formula (1) wherein n is 2 or more.

[0061]

[0062] Here, X in formula (7) １ , X ２ , Y ２ , Y ３ , R ３ is X in formula (1). １ , X ２ , Y ２ , Y ３ , R ３ is the same as:

[0063] As an example, in the step of obtaining a precursor represented by formula (7), 2,5-dimethyl furandicarboxylate and dialkylene glycol can be reacted in the presence of a catalyst such as an organotitanium compound to obtain a precursor represented by formula (7). The reaction can be carried out under a nitrogen atmosphere, at a reaction temperature of 160 to 220°C, and for a reaction time of 4 to 16 hours. As an example, in the step of obtaining a compound represented by formula (1) where n is 2 or more, a mixture of (meth)acryloyl chloride and a solvent can be added dropwise to a mixture of a precursor represented by formula (7) and a solvent, followed by stirring, to obtain a compound represented by formula (1) where n is 2 or more. The reaction can be carried out under a nitrogen atmosphere, at a reaction temperature of 10 to 50°C, and for a reaction time of 2 to 14 hours. Furthermore, the (meth)acryloyl halide can be deactivated by adding distilled water or the like, and the precursor and product can be recovered by purification using an alcoholic solvent such as isopropyl alcohol (IPA), ethyl acetate, methyl ethyl ketone, toluene, or the like, filtration, and drying.

[0064] A method for producing a compound having a structure represented by formula (1-2) according to one embodiment of the present invention can include a step of reacting a precursor represented by formula (7) with isocyanatoethyl(meth)acrylate to obtain a compound having a structure represented by formula (1-2). The reaction can be carried out under a nitrogen atmosphere, at a reaction temperature of 10 to 50°C, and for a reaction time of 2 to 14 hours. Furthermore, the reaction can be carried out by deactivating the isocyanatoethyl(meth)acrylate by adding distilled water or the like, purifying the resulting product with an alcoholic solvent such as isopropyl alcohol (IPA), or with ethyl acetate, methyl ethyl ketone, toluene, or the like, filtering, and drying to recover the precursor and product.

[0065] A method for producing a compound having a structure represented by formula (6) according to one embodiment of the present invention can include a step of reacting furfural with a diol to obtain a precursor represented by formula (8), and a step of reacting the precursor represented by formula (8) with a (meth)acrylate having a halogen atom to obtain a compound having a structure represented by formula (6).

[0066]

[0067] Here, X in formula (8) ３３ , X ３４ is X in formula (6). ３３ , X ３４ is the same as:

[0068] As an example, in the step of obtaining a precursor represented by formula (8), furfural and a diol are reacted in the presence of a catalyst such as p-toluenesulfonic acid monohydrate to obtain a precursor represented by formula (8). The reaction temperature can be 50 to 130°C and the reaction time can be 10 to 20 hours. As an example, in the step of obtaining a compound represented by formula (6), a mixture of (meth)acryloyl chloride and a solvent is dropped into a mixture of a precursor represented by formula (8) and a solvent, followed by stirring, to obtain a compound represented by formula (6). The reaction temperature can be 10 to 50°C and the reaction time can be 2 to 14 hours in a nitrogen atmosphere. In addition, a washing step for removing pyridine and the like, NaHCO ３ Addition of aqueous solution, extraction with solvent such as ethyl acetate, washing with purified water, Mg ２ SO ４ or the like, a dehydration operation by heating and / or a solvent removal operation under reduced pressure, a distillation operation to inactivate the (meth)acryloyl halide by adding distilled water or the like, a precursor and product recovery operation by purifying with an alcohol solvent such as IPA, or ethyl acetate, methyl ethyl ketone, toluene, or the like, filtering, and drying can also be performed.

[0069] A method for producing a compound having a structure represented by formula (6) according to one embodiment of the present invention can include a step of reacting diformylfuran with a diol to obtain a precursor represented by formula (9), and a step of reacting the precursor represented by formula (9) with a (meth)acrylate having a halogen atom to obtain a compound having a structure represented by formula (5).

[0070] A method for producing a compound having a structure represented by formula (6-2) according to one embodiment of the present invention can include a step of reacting a precursor represented by formula (8) with isocyanate ethyl (meth)acrylate to obtain a compound having a structure represented by formula (6-2).

[0071]

[0072] Here, X in formula (9) １３ , X １４ , X ２３ , X ２４ is X in formula (5) １３ , X １４ , X ２３ , X ２４ is the same as:

[0073] As an example, in the step of obtaining a precursor represented by formula (9), furfural and a diol are reacted in the presence of a catalyst such as p-toluenesulfonic acid monohydrate to obtain a precursor represented by formula (9). The reaction temperature can be 50 to 130°C and the reaction time can be 10 to 20 hours. As an example, in the step of obtaining a compound represented by formula (5), a mixture of (meth)acryloyl chloride and a solvent is added dropwise to a mixture of a precursor represented by formula (9) and a solvent, followed by stirring, to obtain a compound represented by formula (5). The reaction temperature can be 10 to 50°C and the reaction time can be 2 to 14 hours in a nitrogen atmosphere. In addition, a washing step for removing pyridine, NaHCO ３ Addition of aqueous solution, extraction with solvent such as ethyl acetate, washing with purified water, Mg ２ SO ４ or the like, a dehydration operation by heating and / or a solvent removal operation under reduced pressure, a distillation operation to inactivate a halogen-containing (meth)acrylate by adding distilled water or the like, a precursor and product recovery operation by purifying with an alcohol solvent such as IPA, or ethyl acetate, methyl ethyl ketone, toluene, or the like, filtering, and drying can also be performed.

[0074] A method for producing a compound having a structure represented by formula (5-2) according to one embodiment of the present invention can include a step of reacting a precursor represented by formula (9) with isocyanatoethyl(meth)acrylate to obtain a compound having a structure represented by formula (5-2). In the reaction, the atmosphere can be a nitrogen atmosphere, the reaction temperature can be 10 to 50°C, and the reaction time can be 2 to 14 hours. Also, a washing step for removing pyridine, a step of removing NaHCO ３ Addition of aqueous solution, extraction with solvent such as ethyl acetate, washing with purified water, Mg ２ SO４ or the like, a dehydration operation by heating and / or a solvent removal operation under reduced pressure, a distillation operation to inactivate isocyanatoethyl (meth)acrylate by adding distilled water or the like, a precursor and product recovery operation by purifying with an alcohol solvent such as IPA, or ethyl acetate, methyl ethyl ketone, toluene, or the like, filtering, and drying can also be performed.

[0075] 3. Cured Product The cured product according to one embodiment of the present invention may contain a linear polymer or a network polymer. Specifically, the cured product according to one embodiment of the present invention may contain at least one of the following: a polymer having two or more repeating units derived from a compound represented by formula (1) or formula (1-2); or a polymer having two or more repeating units derived from a compound represented by formula (5), (6), (5-1), or (5-2). The cured product according to one embodiment of the present invention can be used as a hard coat.

[0076] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples.

[0077] Example 1 Production of Compound I A 100 ml recovery flask was charged with 2.32 g of 2-hydroxyethyl acrylate, 20 ml of ultra-dehydrated toluene (manufactured by Wako Pure Chemical Industries, Ltd.), and 4 ml of pyridine (special grade reagent: manufactured by Wako Pure Chemical Industries, Ltd.), and 10 ml of an ultra-dehydrated toluene solution containing 5.79 g of 2,5-furandicarbonyl dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was gradually added dropwise, followed by stirring at 25°C under a nitrogen atmosphere for 8 hours. Next, the contents of the flask were transferred to a separatory funnel, and 40 ml of toluene and 20 ml of a 1 wt % aqueous hydrochloric acid solution (manufactured by Wako Pure Chemical Industries, Ltd.) were added, followed by the step of removing the pyridine three times. Thereafter, NaHCO ３ 20 ml of an aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was extracted three times with 30 ml of ethyl acetate, and then washed three times with 30 ml of purified water. ２ SO ４ Subsequently, the solvent was removed at 40° C. under reduced pressure of 80 mmHg, and the mixture was distilled at 60° C. under reduced pressure to obtain Compound I represented by the following formula.

[0078]

[0079] Compound I was analyzed and identified by NMR and IR. １ The results of H-NMR and IR are shown in Figure 2. As shown in Figure 1, １ In the H-NMR spectrum, peaks corresponding to A to F of compound I and peaks corresponding to the solvent and raw materials were detected. In addition, as shown in Figure 2, in the IR spectrum, peaks corresponding to the carbonyl group were detected.

[0080] (Example 2) <Production of Compound II> (Production of Precursor II-1) 55.25 g of dimethyl 2,5-furandicarboxylate (manufactured by Tokyo Chemical Industry Co., Ltd.), 63.67 g of diethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.03 g of Orgatix TA-8 (manufactured by Matsumoto Fine Chemical Co., Ltd.) were added to a 300 ml four-neck flask, and the mixture was stirred at 190°C for 10 hours under a nitrogen atmosphere to obtain Precursor II-1 represented by the following formula.

[0081]

[0082] A 100 ml recovery flask was charged with 5.20 g of precursor II-1, 20 ml of N,N-dimethylformamide (ultra-dehydrated: manufactured by Wako Pure Chemical Industries, Ltd.), and 4 ml of pyridine (special grade reagent: manufactured by Wako Pure Chemical Industries, Ltd.). 10 ml of a solution of 1.35 g of acryloyl chloride (manufactured by Wako Pure Chemical Industries, Ltd.) in ultra-dehydrated N,N-dimethylformamide was slowly added dropwise, and the mixture was stirred at room temperature under a nitrogen atmosphere for 8 hours. Next, 3 ml of distilled water was added to deactivate unreacted acryloyl chloride. The reaction solution was then slowly added dropwise to 300 ml of IPA to purify the resin. The resin was filtered through a SUS200 mesh sieve and dried under reduced pressure to obtain compound II represented by the following formula:

[0083]

[0084] (Example 3) <Production of Compound III> (Production of Precursor III-1) A 100 ml recovery flask was charged with 1.66 ml of furfural (manufactured by Wako Pure Chemical Industries, Ltd.), 5.9045 g of 1,6-hexanediol (manufactured by TCI), 40 mg of p-toluenesulfonic acid monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.), 4 ml of N,N-dimethylformamide (ultra-dehydrated: manufactured by Wako Pure Chemical Industries, Ltd.), and 10 ml of hexane (special grade reagent: manufactured by Wako Pure Chemical Industries, Ltd.), and the mixture was heated to 90°C and stirred for 16 hours. The reaction solution was cooled to 25°C, and NaHCO ３ 20 ml of an aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The product was extracted three times with 40 ml of ethyl acetate, and then washed three times with 30 ml of purified water. ２ SO ４ Subsequently, the solvent was removed at 40° C. under reduced pressure of 80 mmHg, and the mixture was distilled at 60° C. under reduced pressure to obtain a precursor III-1 represented by the following formula:

[0085]

[0086] A 100 ml recovery flask was charged with 1.57 g of precursor III-1, 10 ml of ultra-dehydrated toluene (manufactured by Wako Pure Chemical Industries, Ltd.), and 2 ml of pyridine (special grade reagent: manufactured by Wako Pure Chemical Industries, Ltd.), and 5 ml of ultra-dehydrated toluene solution containing 1.35 g of acryloyl chloride (manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added dropwise, followed by stirring at room temperature under a nitrogen atmosphere for 8 hours. Next, 20 ml of toluene and 20 ml of 1 wt% aqueous hydrochloric acid solution (manufactured by Wako Pure Chemical Industries, Ltd.) were added, and the mixture was washed three times to remove the pyridine, followed by adding NaHCO 3 . ３ 20 ml of an aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The mixture was extracted three times with 30 ml of ethyl acetate, and then washed three times with 30 ml of purified water. ２ SO ４ Subsequently, the solvent was removed at 40° C. under reduced pressure of 80 mmHg, and the mixture was distilled at 60° C. under reduced pressure to obtain Compound III represented by the following formula.

[0087]

[0088] (Example 4) <Production of Compound IV> (Production of Precursor IV-1) A 100 ml recovery flask was charged with 2.48 g of diformylfuran (Tokyo Chemical Industry Co., Ltd.), 5.32 g of 1,6-hexanediol (TCI), 40 mg of p-toluenesulfonic acid monohydrate (Wako Pure Chemical Industries, Ltd.), 4 ml of N,N-dimethylformamide (ultra-dehydrated: Wako Pure Chemical Industries, Ltd.), and 10 ml of hexane (special reagent grade: Wako Pure Chemical Industries, Ltd.), and the mixture was heated to 90°C and stirred for 16 hours. The reaction solution was cooled to 25°C, and NaHCO ３ 20 ml of an aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The product was extracted three times with 40 ml of ethyl acetate, and then washed three times with 30 ml of purified water. ２ SO ４ Subsequently, the solvent was removed at 40° C. under reduced pressure of 80 mmHg, and the mixture was distilled at 60° C. under reduced pressure to obtain precursor IV-1 represented by the following formula: A 100 ml recovery flask was charged with 2.80 g of precursor IV-1, 20 ml of ultra-dehydrated toluene (manufactured by Wako Pure Chemical Industries), and 4 ml of pyridine (special grade reagent: manufactured by Wako Pure Chemical Industries). 10 ml of ultra-dehydrated toluene solution containing 2.70 g of acryloyl chloride (manufactured by Wako Pure Chemical Industries) was gradually added dropwise, and the mixture was stirred at room temperature under a nitrogen atmosphere for 8 hours. Next, 40 ml of toluene and 20 ml of 1 wt% aqueous hydrochloric acid solution (manufactured by Wako Pure Chemical Industries) were added, and the mixture was washed three times to remove the pyridine. Then, NaHCO ３ 20 ml of an aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The mixture was extracted three times with 30 ml of ethyl acetate, and then washed three times with 30 ml of purified water. ２ SO ４ Subsequently, the solvent was removed at 40° C. under reduced pressure of 80 mmHg, and the mixture was distilled at 60° C. under reduced pressure to obtain Compound IV represented by the following formula.

[0089]

[0090] Example 5 Preparation of Compound V A 100 ml recovery flask was charged with 5.20 g of the precursor II-1, 20 ml of N,N-dimethylformamide (ultra-dehydrated: manufactured by Wako Pure Chemical Industries, Ltd.), and 4 ml of pyridine (special grade reagent: manufactured by Wako Pure Chemical Industries, Ltd.). 10 ml of a solution of 2.11 g of isocyanatoethyl acrylate in ultra-dehydrated N,N-dimethylformamide was slowly added dropwise, and the mixture was stirred at room temperature under a nitrogen atmosphere for 8 hours. Next, 3 ml of distilled water was added to deactivate unreacted isocyanatoethyl acrylate. The reaction solution was then slowly added dropwise to 300 ml of IPA to purify the resin. The resin was filtered through a SUS200 mesh and dried under reduced pressure to obtain Compound V represented by the following formula:

[0091]

[0092] Example 6 Preparation of Compound VI In a 100 ml recovery flask, 1.57 g of precursor III-1, 10 ml of ultra-dehydrated toluene (manufactured by Wako Pure Chemical Industries, Ltd.), and 2 ml of pyridine (special grade reagent: manufactured by Wako Pure Chemical Industries, Ltd.) were charged, and 5 ml of ultra-dehydrated toluene solution of 2.11 g of isocyanate ethyl acrylate was gradually added dropwise, followed by stirring at room temperature under a nitrogen atmosphere for 8 hours. Next, 20 ml of toluene and 20 ml of 1 wt % aqueous hydrochloric acid solution (manufactured by Wako Pure Chemical Industries, Ltd.) were added, and the mixture was washed three times to remove the pyridine, followed by NaHCO 3 . ３ 20 ml of an aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The mixture was extracted three times with 30 ml of ethyl acetate, and then washed three times with 30 ml of purified water. ２ SO ４ Subsequently, the solvent was removed at 40° C. under reduced pressure of 80 mmHg, and the mixture was distilled at 60° C. under reduced pressure to obtain a compound VI represented by the following formula.

[0093]

[0094] <Preparation of Cured Film> 80 parts by mass of the compounds obtained in Examples 1 to 6, 20 parts by mass of butyl acrylate, and 1 part by mass of a photoinitiator (IRGACURE184) were blended to obtain a composition for preparing a cured film. The composition was applied to a release-treated polyethylene terephthalate (PET) film using a doctor blade so that the film thickness after UV irradiation would be 25 μm, and then covered with another release-treated PET film for covering. With the film sandwiched between the two PET films, a UV lamp was used to illuminate the film at an intensity of 2.5 mW / cm. ２ The sheet was irradiated with light of 1000 kJ / min for 2 minutes to prepare a sheet having a cured film.

[0095] (Gel Fraction) From the sheet having the cured film obtained above, about 0.1 g of the cured film was collected in a sample bottle, 30 ml of ethyl acetate was added, and the mixture was shaken for 4 hours. The contents of the sample bottle were then filtered through a 200-mesh stainless steel wire mesh, and the residue on the wire mesh was dried at 100°C for 2 hours, and the dry weight was measured to determine the gel fraction. The following formula was used to calculate the gel fraction: Gel fraction (%) = (dry weight / collected weight of cured film) x 100 (%)

[0096] (Pencil hardness) One of the release-treated PET films was peeled off from the sheet having the cured film obtained above, and the pencil hardness of the exposed cured film was measured according to the method of JIS K 5600-5-4 (pencil method). The maximum hardness at which no change in appearance was observed was taken as the evaluation value.

[0097]

Claims

1. A compound having a furan structure and two or more (meth)acryloyl groups in the molecule.

2. The compound according to claim 1, wherein at least two of the (meth)acryloyl groups are located at the terminals of the molecule.

3. The compound according to claim 2, represented by the following formula (1). (In formula (1), X １ , X ２ are each independently an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylene cycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylene alkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylene arylene group having 7 to 30 carbon atoms which may have a substituent, an arylene alkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent. When X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom. Y １ , Y ２ , Y ３ , Y ４ are each independently O or NR ３ . R １ , R ２ , R ３ are each independently H or CH ３ or CH ２ CH ３ . n is a natural number from 1 to 50).

4. The compound according to claim 2, having a structure represented by the following formula (2). (In formula (2), X ３ , X ４ are each independently an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylene cycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylene alkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylene arylene group having 7 to 30 carbon atoms which may have a substituent, an arylene alkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a hetero atom which may have a substituent, a divalent four-membered ring containing a hetero atom which may have a substituent, a divalent five-membered ring containing a hetero atom which may have a substituent, and a divalent six-membered ring containing a hetero atom which may have a substituent. When X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent hetero atom. Y ５ and Y ６ are each independently O or NR ６ . R ４ , R ５ , R ６ are each independently H or CH ３ or CH ２ CH ３ (wherein).) 5. The compound according to claim 2, having a structure represented by the following formula (1-2). (In formula (1-2), X ５ , X ６ are each independently an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylene cycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylene alkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylene arylene group having 7 to 30 carbon atoms which may have a substituent, an arylene alkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent. When X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom. Y ７ and Y ８ are each independently O or NR ９ . R ７ , R ８ , R ９ are each independently H or CH ３ or CH ２ CH ３ . m is a natural number from 1 to 50.) 6. The compound according to claim 2, having a structure represented by the following formula (2-2). (In formula (2-2), X ７ , X ８ are each independently an ethylene oxide group, a propylene oxide group, an alkylene group having 2 or more carbon atoms which may have a substituent, an alkenylene group having 2 or more carbon atoms which may have a substituent, an alkynylene group having 2 or more carbon atoms which may have a substituent, a cycloalkylene group having 3 or more carbon atoms which may have a substituent, an alkylene cycloalkylene group having 4 to 30 carbon atoms which may have a substituent, a cycloalkylene alkylene group having 4 to 30 carbon atoms, an arylene group having 6 to 18 carbon atoms which may have a substituent, an alkylene arylene group having 7 to 30 carbon atoms which may have a substituent, an arylene alkylene group having 7 to 30 carbon atoms which may have a substituent, a divalent three-membered ring containing a heteroatom which may have a substituent, a divalent four-membered ring containing a heteroatom which may have a substituent, a divalent five-membered ring containing a heteroatom which may have a substituent, and a divalent six-membered ring containing a heteroatom which may have a substituent, and when X contains an alkylene group, at least one carbon atom contained in the alkylene group may be substituted with a divalent heteroatom, R １０ , R １１ are each independently H or CH ３ or CH ２ CH ３ .)

Images