Compound, composition, cured film, and method for producing cured film

Abstract

To provide a composition capable of forming a cured film excellent in flexibility.SOLUTION: A compound represented by the following general formula (1) is provided. R1 and R2 each independently represent a C1-10 aliphatic hydrocarbon group or a C1-10 heteroatom-containing hydrocarbon group and may be linked to each other to form a heterocyclic ring containing a nitrogen atom; R3, R4 and R5 each independently represent a hydrogen atom or a C1-3 alkyl group; X and Y each independently represent a divalent linking group; and a represents a number of 1 or more and 10 or less. A composition containing the compound and a polymerization initiator is also provided.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a compound having an amide bond (-NH-C(=O)-), a composition using the compound, a cured film, and a method for producing the cured film. [Background technology]

[0002] Compounds having a double bond between carbon and carbon atoms can be polymerized (cured) using a polymerization initiator. Among them, compounds having an amide bond are used as coating materials in various fields such as paints, inks, and adhesives. For example, Patent Document 1 discloses a coating agent and its cured product that are excellent in transparency, storage stability, and coatability by using a specific amide compound and a polymerization initiator. Patent Document 2 discloses a polymerizable composition containing a polymerizable compound having an amide group and an ethylenically unsaturated group as a material for forming a coating material having excellent acid component scavenging properties and high adhesive strength. Patent Document 3 discloses that a strong polymer is formed in the presence of water by using a specific acrylamide-based polymerizable monomer in an adhesive composition. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. WO2021 / 002307 [Patent Document 2] International Publication No. WO2021 / 044986 [Patent Document 3] JP 2020-183513 A Summary of the Invention [Problem to be solved by the invention]

[0004] Conventional compositions containing compounds having an amide bond can form cured films with high hardness, but have the problem of shrinkage during curing and lack of flexibility.

[0005] Therefore, an object of the present invention is to provide a compound capable of forming a cured film having excellent flexibility. [Means for solving the problem]

[0006] As a result of intensive research aimed at solving the above problems, the present inventors have found that the above problems can be solved by using a specific compound, and have thus completed the present invention. That is, the present invention provides a compound represented by the following general formula (1).

[0007] [ka] (R 1 and R 2 each independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms or a heteroatom-containing hydrocarbon group; R 1 and R 2 may be linked together to form a heterocycle containing a nitrogen atom, R 3 , R 4 and R 5 each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X and Y each independently represent a divalent linking group; a represents a number between 1 and 10.

[0008] The present invention also provides a composition comprising the above compound and a polymerization initiator.

[0009] The present invention further provides a cured film of the above composition.

[0010] Furthermore, the present invention provides a method for producing a cured film, comprising a curing step of irradiating the above composition with active energy rays. Effect of the Invention

[0011] The compound of the present invention can provide a composition capable of forming a cured film having excellent flexibility. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention relates to a compound having an amide bond, a composition using the compound, a cured film, and a method for producing the cured film. The present invention will be described in detail below.

[0013] A. Compound The present disclosure provides a compound represented by the following general formula (1):

[0014] [ka]

[0015] R 1 and R 2 R each independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms or a heteroatom-containing hydrocarbon group having 1 to 10 carbon atoms. 1 and R 2 may be linked to each other to form a heterocycle containing a nitrogen atom. R 3 , R 4 and R 5 each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. X and Y each independently represent a divalent linking group. a represents a number from 1 to 10.

[0016] R in the above general formula (1) 1 and R 2 Examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms include saturated aliphatic hydrocarbon groups having 1 to 10 carbon atoms, unsaturated aliphatic hydrocarbon groups having 2 to 10 carbon atoms, and alicyclic aliphatic hydrocarbon groups having 3 to 10 carbon atoms. The saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms is an aliphatic hydrocarbon group that does not have a cyclic structure and does not have an unsaturated bond (double bond or triple bond) between carbon atoms, and may be linear or branched. Examples of the saturated aliphatic hydrocarbon group include alkyl groups. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a 2-pentyl group, a 3-pentyl group, a hexyl group, a heptyl group, a 2-heptyl group, a 3-heptyl group, an octyl group, and a 2-ethylhexyl group.

[0017] The unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms does not have a cyclic structure and represents an aliphatic hydrocarbon group having an unsaturated bond between some carbon atoms, and may be linear or branched. Examples of the unsaturated aliphatic hydrocarbon group include a vinyl group, an allyl group, a butenyl group, a pentenyl group, and a hexenyl group.

[0018] The alicyclic aliphatic hydrocarbon group having 3 to 10 carbon atoms is an aliphatic hydrocarbon group having a cyclic structure, and may have an unsaturated bond between some carbon atoms. The cyclic structure is a structure in which carbon atoms are bonded in a ring shape, and examples of the cyclic structure include cycloalkane and cycloalkene. Examples of the alicyclic aliphatic hydrocarbon group include cycloalkyl groups such as cyclopentyl and cyclohexyl groups; cycloalkenyl groups such as cyclopentenyl and cyclohexenyl groups; cycloalkylalkyl groups in which some of the hydrogen atoms of the above-mentioned alkyl groups are substituted with cycloalkyl groups; and cycloalkenylalkyl groups in which some of the hydrogen atoms of the above-mentioned alkyl groups are substituted with cycloalkenyl groups.

[0019] Above R 1 and R 2Examples of the heteroatom-containing hydrocarbon group having 1 to 10 carbon atoms and represented by the formula (I) include groups in which some or all of the hydrogen atoms of the above-mentioned aliphatic hydrocarbon group have been substituted with heteroatom-containing groups, groups in which one or more methylene groups in the aliphatic hydrocarbon group have been substituted with -O-, -S-, -OCO-, -CO-O-, etc., or groups having both. Examples of the heteroatom-containing group include a halogeno group, a hydroxyl group, a carboxyl group, an oxyalkyl group, an epoxy group, a formyl group, a nitro group, a cyano group, an amino group, a thiol group, a silyl group, a sulfonate group, and a phosphate group. Examples of the halogeno group include a fluoro group, a chloro group, a bromo group, and an iodo group. Examples of the heteroatom-containing hydrocarbon group having 1 to 10 carbon atoms include a methoxyethyl group, a dimethylaminomethyl group, a trimethylsilylmethyl group, and a triethylsilylethyl group.

[0020] Above R 1 and R 2 In the heterocycle formed by bonding together and containing a nitrogen atom, the heterocycle may be a non-aromatic heterocycle or an aromatic heterocycle.

[0021] The non-aromatic heterocycle refers to a ring having a structure in which a nitrogen atom and one or more atoms selected from carbon atoms, oxygen atoms, and sulfur atoms are bonded in a ring shape, and which does not have aromaticity. Examples of the non-aromatic heterocycle include an aziridine ring, a diaziridine ring, an azetidine ring, a diazetidine ring, an azirine ring, a pyrrolidine ring, a 3-pyrroline ring, a piperidine ring, a piperazine ring, an imidazolidine ring, a pyrazolidine ring, a morpholine ring, a thiomorpholine ring, a hexahydro-1,3,5-triazine ring, an oxazolidine ring, an isoxazolidine ring, a thiazolidine ring, an isothiazolidine ring, and a hexamethyleneimine ring (azepane).

[0022] The aromatic heterocycle has a structure in which a nitrogen atom and one or more atoms selected from carbon atoms, oxygen atoms, and sulfur atoms are bonded in a ring shape, and represents a ring having aromaticity. Examples of the aromatic heterocycle include a pyrrole ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a triazole ring, a furazan ring, an oxadiazole ring, a thiadiazole ring, a dithiazole ring, a tetrazole ring, an oxatetrazole ring, a pyridine ring, a tridiazine ring, a tetrazine ring, and a pentaazine ring.

[0023] Above R 1 and R 2 In the heterocycle formed by linking together and containing a nitrogen atom, some of the hydrogen atoms in the heterocycle may be substituted with the above-mentioned heteroatom-containing group or an alkyl group having 1 to 5 carbon atoms, or the heterocycle may not have a substituent.

[0024] R in the above general formula (1) 3 , R 4 and R 5 The alkyl group having 1 to 3 carbon atoms represented by the above R 1 In the alkyl group represented by the formula (I) and (II), a group having a specific number of carbon atoms is included.

[0025] Examples of the divalent linking group represented by X and in the above general formula (1) include -S-, -O-, an alkylene group having 1 to 5 carbon atoms, and groups formed by a combination of these groups provided that oxygen atoms are not bonded to each other. X and Y may be the same group or different groups. When a is an integer of 2 or more, the multiple Xs may be different groups.

[0026] Examples of the alkylene group having 1 to 5 carbon atoms include a methylene group, a methylidene group, an ethylene group, an ethylidene group, a propylene group, a propylidene group, an isopropylidene group, a methylethylene group, a tetramethylene group, a 1,1-dimethylethylene group, a 1,2-dimethylethylene group, a 1-methylpropylene group, a 2-methylpropylene group, a pentamethylene group, a 1-ethylpropylene group, a 1-methylbutylene group, and a 2-methylbutylene group.

[0027] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, R 1 and R 2 but It is preferably a saturated hydrocarbon group having 1 to 10 carbon atoms, More preferably, the alkyl group has 1 to 10 carbon atoms. More preferably, the alkyl group has 1 to 5 carbon atoms. It is particularly preferable that the alkyl group has 1 to 4 carbon atoms. Most preferably it is a methyl group, an ethyl group, a propyl group or an isopropyl group.

[0028] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility and hardness, 1 and R 2 are preferably linked to each other to form a heterocycle containing a nitrogen atom, It is more preferable that the heterocycle is a 4- to 7-membered ring, It is further preferable that the heterocycle is a 5-membered or 6-membered ring, It is particularly preferred that the heterocycle is a six-membered ring. It is particularly preferred that the heterocycle is a non-aromatic heterocycle, It is particularly preferable that the heterocycle is a pyrrolidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring, or a hexahydro-1,3,5-triazine ring, The heterocycle is most preferably a pyrrolidine ring, a piperazine ring or a morpholine ring.

[0029] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, it is preferable that at least one of X and Y is an alkylene group having 1 to 3 carbon atoms, It is more preferable that both X and Y are alkylene groups having 1 to 3 carbon atoms. It is more preferred that both X and Y are ethylene or propylene groups.

[0030] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, R 3 , R 4 and R 5 It is preferable that all of the groups are hydrogen atoms or methyl groups, and it is particularly preferable that all of the groups are hydrogen atoms.

[0031] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, a is more preferably a number of 1 or more and 5 or less, even more preferably a number of 1 or more and 3 or less, and particularly preferably a number of 1 or 2.

[0032] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility and adhesion, the acrylic equivalent of the compound represented by general formula (1) is It is preferable that the content is 100 g / eq. or more. More preferably, it is 105 g / eq. or more and 200 g / eq. or less. More preferably, the elastic modulus is 110 g / eq. or more and 160 g / eq. or less. It is particularly preferable that the elastic modulus is 115 g / eq. or more and 145 g / eq. or less. In the present disclosure, the "acrylic equivalent" refers to the value obtained by dividing the molecular weight of a compound by the total number of acrylic and methacrylic groups contained in the compound.

[0033] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility and adhesion, the molecular weight of the compound represented by general formula (1) is It is preferable that the ratio is 200 or more and 700 or less. More preferably, it is 250 or more and 550 or less, More preferably, it is 300 or more and 480 or less. It is particularly preferable that the molecular weight is 330 or more and 450 or less.

[0034] Specific examples of the compound represented by the above general formula (1) include the following compounds No. 1 to No. 14. However, the present invention is not limited to the following compounds.

[0035] [ka]

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[0040] The method for producing the compound represented by the above general formula (1) is not particularly limited, and the compound can be produced by a known synthesis method. For example, a compound represented by the general formula (1) can be produced by reacting a polyalkylene polyamine with R 1 and R 2 The compound represented by the above general formula (1) can be produced by reacting the compound represented by the above general formula (1) with a compound having a (meth)acrylamide group having the formula (I) and then reacting the compound represented by the above general formula (1) with a compound having a (meth)acrylamide group having the formula (I) and then further ... further reacting the compound represented by the above general formula (1) with a compound having a (meth)acrylamide group having the formula (I)

[0041] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, As the compound represented by the above general formula (1), It is preferred that the composition contains No. 2, No. 8, No. 11 or No. 13, More preferably, it contains No. 8, No. 11 or No. 13, It is particularly preferred to include No. 8 or No. 13. Among these, it is particularly preferable to contain No. 13, from the viewpoint of facilitating the formation of a cured film excellent in flexibility and hardness.

[0042] B. Composition Next, the composition of the present disclosure will be described.

[0043] B1. Compound represented by general formula (1) In the composition of the present disclosure, the compound represented by the above general formula (1) is contained as a curable component. The structure of the compound represented by the above general formula (1) is explained in the section "A. Compound", so the explanation here is omitted. In the composition of the present disclosure, the curable component may be only the compound represented by the above general formula (1), or may be a combination of the compound represented by the above general formula (1) and other curable components. In addition, as the curable component, one type of compound represented by the above general formula (1) may be used alone, or two or more types may be used in combination.

[0044] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, The content of the compound represented by the general formula (1) in 100 parts by mass of the curable component is More preferably, the content is 5 parts by mass or more and 100 parts by mass or less. More preferably, the content is 10 parts by mass or more and 100 parts by mass or less. It is particularly preferable that the content is 20 parts by mass or more and 100 parts by mass or less. It is particularly preferable that the amount is 30 parts by mass or more and 100 parts by mass or less. The most preferred range is 50 parts by mass or more and 100 parts by mass or less.

[0045] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the compound represented by the above general formula (1) is, per 100 parts by mass of the solid content of the composition, It is preferably 3 parts by mass or more and 98 parts by mass or less, More preferably, the content is 10 parts by mass or more and 97 parts by mass or less. It is more preferably from 20 parts by mass to 96 parts by mass. It is particularly preferable that the content is 40 parts by mass or more and 95 parts by mass or less.

[0046] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the compound represented by the above general formula (1) in 100 parts by mass of the composition is It is preferably 1 part by mass or more and 80 parts by mass or less, More preferably, the content is 5 parts by mass or more and 70 parts by mass or less. It is more preferable that the content is 10 parts by mass or more and 60 parts by mass or less. It is particularly preferable that the content is 15 parts by mass or more and 50 parts by mass or less.

[0047] B2. Other hardening components The composition of the present disclosure may contain other curable components in addition to the compound represented by the above general formula (1). Examples of the other curable components include radically polymerizable components.

[0048] Examples of the radically polymerizable component include a monomer having a (meth)acrylate group (hereinafter, sometimes referred to as "(meth)acrylate"), a monomer having a (meth)acrylamide group (excluding the compound represented by the above general formula (1)), a vinyl ether compound, and the like. The (meth)acrylate group represents an acrylate group or a methacrylate group, and the (meth)acrylamide group represents an acrylamide group or a methacrylamide group.

[0049] The above-mentioned (meth)acrylate may be one in which various groups are bonded to the ester end of the (meth)acrylate group.The above-mentioned (meth)acrylate may be, for example, monofunctional (meth)acrylate monomer, such as alkyl (meth)acrylate such as chain alkyl (meth)acrylate and alicyclic alkyl (meth)acrylate; aromatic (meth)acrylate; hydroxyl group-containing (meth)acrylate; epoxy group-containing (meth)acrylate; alkoxy group or phenoxy group-containing (meth)acrylate; halogeno group-containing (meth)acrylate; alkylaminoalkyl (meth)acrylate; etc.

[0050] The chain alkyl (meth)acrylate may be a (meth)acrylate having a chain alkyl group at the ester end. Examples of the chain alkyl group include an alkyl group having 1 to 20 carbon atoms and not having an aromatic hydrocarbon ring such as a benzene ring or an aliphatic hydrocarbon ring such as a cyclohexyl ring. Examples of the chain alkyl (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, 2-methyl-2-nitropropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, s-butyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, tert-pentyl (meth)acrylate, 3-pentyl (meth)acrylate, 2,2-dimethylbutyl (meth)acrylate, n-hexyl (meth)acrylate, cetyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 4-methyl-2-propylpentyl (meth)acrylate, and n-octadecyl (meth)acrylate.

[0051] The alicyclic alkyl (meth)acrylate may be a (meth)acrylate having an aliphatic hydrocarbon ring such as a cyclohexyl ring. Examples of the alicyclic alkyl (meth)acrylate include cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, and isobornyl (meth)acrylate.

[0052] The aromatic (meth)acrylate may be one in which the group to which the (meth)acrylate is bonded contains an aromatic hydrocarbon ring. An example of the aromatic (meth)acrylate is benzyl (meth)acrylate.

[0053] The hydroxyl group-containing (meth)acrylate may be one in which the group to which the (meth)acrylate group is bonded contains a hydroxyl group. Examples of the hydroxyl group-containing (meth)acrylate include hydroxyalkyl (meth)acrylates such as 2-hydroxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, and 2,3-dihydroxypropylmethyl-butyl (meth)methacrylate; and hydroxyalkyl cycloalkane (meth)acrylates such as (4-hydroxymethylcyclohexyl)methyl (meth)acrylate.

[0054] The epoxy group-containing (meth)acrylate may be one in which the group to which the (meth)acrylate group is bonded is a group containing an epoxy group. An example of the epoxy group-containing (meth)acrylate is glycidyl (meth)acrylate.

[0055] The alkoxy- or phenoxy-group-containing (meth)acrylate may be one in which the group to which the (meth)acrylate group is bonded is a group containing an alkoxy group or a phenoxy group. Examples of the alkoxy group- or phenoxy group-containing (meth)acrylate include 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-methoxymethoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethyl carbitol (meth)acrylate, phenoxyethyl (meth)acrylate, and phenol ethylene oxide-modified (meth)acrylate.

[0056] The halogeno group-containing (meth)acrylate may be one in which the group to which the (meth)acrylate group is bonded contains a halogen atom. Examples of the halogeno group-containing (meth)acrylate include 2,2,2-trifluoroethyl (meth)acrylate, 2,2,2-trifluoroethylethyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, hexafluoropropyl (meth)acrylate, octafluoropentyl (meth)acrylate, and heptadecafluorodecyl (meth)acrylate.

[0057] The alkylaminoalkyl (meth)acrylate may be one in which the group to which the (meth)acrylate group is bonded contains an alkylamino group. Examples of the alkylaminoalkyl (meth)acrylate include dimethylaminoethyl (meth)acrylate.

[0058] The monomer having a (meth)acrylamide group may have various groups bonded to the amide terminal of the (meth)acrylamide group. Examples of the monomer having the (meth)acrylamide group include monofunctional (meth)acrylamide monomers such as (meth)acrylamide; hydroxyl group-containing (meth)acrylamides such as hydroxyethyl(meth)acrylamide and N-methylol(meth)acrylamide; alkoxy group- or phenoxy group-containing (meth)acrylamides such as N-methoxymethyl(meth)acrylamide and N-ethoxymethyl(meth)acrylamide; and nitrogen ring-containing (meth)acrylamides such as (meth)acryloylmorpholine and (meth)acryloylpiperazine.

[0059] The radically polymerizable component may also contain a polyfunctional monomer having a plurality of (meth)acrylate groups or (meth)acrylamide groups. Examples of the polyfunctional monomer include (poly)ethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 1,2-ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, tripropylene glycol di ... Examples of the ester compounds include ester compounds of polyhydric alcohols such as glycol diacrylate, 1,9-nonanediol diacrylate, tricyclodecane dimethanol diacrylate, cyclic trimethylolpropane formal acrylate, dioxane glycol diacrylate, and EO-modified diglycerin tetraacrylate with (meth)acrylic acid; epoxy acrylates having a structure in which a (meth)acrylate group is added to a polyfunctional epoxy compound; polyester acrylates having a structure in which a (meth)acrylate group is added to a polyester polyol; and urethane acrylates having a structure containing a urethane bond and a (meth)acrylate group, which are obtained by reacting a polyol, an isocyanate, and a (meth)acrylate.

[0060] The vinyl ether compound refers to a compound that has a vinyl ether structure and does not have an epoxy group, a (meth)acrylate group, or an oxetanyl group. Examples of the vinyl ether compound include compounds described in JP-A-2022-42418.

[0061] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, it is preferable that the radical polymerizable component contains a monomer having a (meth)acrylamide group, and it is more preferable that the radical polymerizable component contains a hydroxyl group-containing (meth)acrylamide or a nitrogen-containing ring-containing (meth)acrylamide.

[0062] When the composition of the present disclosure contains the above-mentioned radically polymerizable component, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the above-mentioned radically polymerizable component is, per 100 parts by mass of the curable component, It is preferably 5 parts by mass or more and 90 parts by mass or less, More preferably, the content is 10 parts by mass or more and 85 parts by mass or less. More preferably, the content is 15 parts by mass or more and 80 parts by mass or less. It is particularly preferable that the content is 20 parts by mass or more and 70 parts by mass or less. The most preferred range is 25 parts by weight or more and 50 parts by weight or less.

[0063] When the composition of the present disclosure contains the radically polymerizable component, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the radically polymerizable component is, per 100 parts by mass of the solid content of the composition, It is preferably 5 parts by mass or more and 85 parts by mass or less, More preferably, the content is 10 parts by mass or more and 70 parts by mass or less. More preferably, the content is 15 parts by mass or more and 60 parts by mass or less. It is particularly preferable that the content is 20 parts by mass or more and 50 parts by mass or less.

[0064] When the composition of the present disclosure contains the radical polymerizable component, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the radical polymerizable component per 100 parts by mass of the composition is: It is preferably 1 part by mass or more and 50 parts by mass or less, More preferably, the content is 3 parts by mass or more and 40 parts by mass or less. More preferably, the content is 5 parts by mass or more and 30 parts by mass or less. It is particularly preferable that the content is 7 parts by mass or more and 20 parts by mass or less.

[0065] B3. Polymerization initiator The polymerization initiator is a component that initiates the polymerization (curing) reaction of the compound represented by the above general formula (1). The polymerization initiator is not particularly limited as long as it is one or more materials capable of generating radicals in response to light irradiation, and known materials can be used. Examples of the polymerization initiator include compounds described in International Publication WO2021 / 002307. From the viewpoint of facilitating polymerization of the composition of the present disclosure, it is preferable to use a photoradical polymerization initiator as the polymerization initiator, and it is more preferable to use an acetophenone compound or an acylphosphine compound.

[0066] In the composition of the present disclosure, when the solvent described below contains an aqueous solvent, the polymerization initiator is preferably water-soluble. That is, the polymerization initiator is preferably a water-soluble polymerization initiator. This is because it allows the use of an aqueous solvent as a solvent, and improves the storage stability and coatability of materials using an aqueous solvent.

[0067] When a water-soluble polymerization initiator is used, the solubility of the polymerization initiator in an aqueous solvent is not particularly limited, but it is preferable that the polymerization initiator is soluble in water at 25° C. in an amount of 1% by mass or more. This is because it makes it easier to prepare a composition using an aqueous solvent.

[0068] Examples of the water-soluble polymerization initiator include the compounds represented by the following B1 to B37, but the present invention is not limited to these compounds.

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[0083] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the polymerization initiator is, in 100 parts by mass of the curable component, It is preferably 0.1 parts by mass or more and 20 parts by mass or less, More preferably, the content is 0.5 parts by mass or more and 15 parts by mass or less. It is more preferable that the amount is 1 part by mass or more and 10 parts by mass or less.

[0084] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the polymerization initiator is, per 100 parts by mass of the solid content of the composition, It is preferably 0.1 parts by mass or more and 20 parts by mass or less, More preferably, the content is 0.5 parts by mass or more and 15 parts by mass or less. It is more preferable that the amount is 1 part by mass or more and 10 parts by mass or less.

[0085] In the present disclosure, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the polymerization initiator in 100 parts by mass of the composition is It is preferably 0.1 parts by mass or more and 20 parts by mass or less, More preferably, the content is 0.5 parts by mass or more and 10 parts by mass or less. It is more preferable that the content is 0.8 parts by mass or more and 5 parts by mass or less.

[0086] B4.Leveling agent The composition of the present disclosure preferably further contains a leveling agent. The leveling agent can adjust the flowability of the composition of the present disclosure and provide a coating film obtained by applying the composition with excellent smoothness. There are no particular limitations on the type of the leveling agent, so long as it can reduce the surface tension of the composition of the present disclosure and impart surface orientation. The composition of the present disclosure preferably contains a silicone surfactant or a fluorine-based surfactant as a leveling agent, and more preferably contains a fluorine-based surfactant, because the surface tension can be reduced with a smaller amount added, making it easier to improve repelling and dents in the coating film.

[0087] The silicone surfactant is not particularly limited as long as it has a silicon-containing group as a hydrophobic group, and examples thereof include polydimethylsiloxane, polymethylalkylsiloxane, silicone-modified acrylic, polyether-modified polydimethylsiloxane, polyester-modified hydroxyl group-containing polydimethylsiloxane, and polyetherester-modified hydroxyl group-containing polydimethylsiloxane.

[0088] Examples of commercially available silicone surfactants include: DOWSIL (registered trademark) SH-29PA, FZ-2105, 67ADDITIVE, 8618ADDITIVE, 3ADDITIVE, 56ADDITIVE (all manufactured by Dow Corning Toray Co., Ltd.); TEGO (registered trademark) Flow 425, Glide 100, Glide 110, Glide 432, etc. (all manufactured by Evonik); F-251, F-253, F-410, F-430, F-444, F-477, F-510, F-551-A, F-552, F-553, F-554, F-555-A, F-556, F-558, F-559, F-560, F-561, F-562, F-563, F-565, F-568, F-569, F-570, F-571, F-575, F-576, R-01, R-40, R-40-LM, R-41, R-41-LM, RS-72-A, RS-75-A, RS-75-NS, RS-78, RS-90 and DS-21, etc. (all manufactured by DIC Corporation); BYK (registered trademark)-300, 306, 307, 310, 315, 313, 320, 322, 323, 325, 330, 331, 333, 337, 341, 344, 347, 348, 349, 370, 375, 377, 378, UV3500, UV3510, UV3570, 3550, SILCLEAN3700 and SILCLEAN3720, etc. (all manufactured by BYK); Polyflow (registered trademark) KL-400X, KL-400HF, KL-401, KL-402, KL-403, and KL-404 (all manufactured by Kyoeisha Chemical Co., Ltd.); Examples of the antibacterial agents include KP-323, KP-341, KP-104, KP0110, and KP-112 (all manufactured by Shin-Etsu Chemical Co., Ltd.).

[0089] The fluorosurfactant is not particularly limited as long as it is a surfactant having a fluorine-containing group as a hydrophobic group, and examples thereof include perfluorooctanesulfonic acid and perfluorocarboxylic acid. Examples of commercially available fluorosurfactants include: Megafac (registered trademark) F-251, F-253, F-410, F-444, F-477, F-551-A, F-554, F-556, F-559, F-560, F-569, F-570, F-575, R-01, R-40, R-40-LM, R-41, R-41-LM and DS-21, etc. (all manufactured by DIC Corporation); Surflon (registered trademark) S-211, S-221, S-231, S-232, S-233, S-241, S-242, S-242L, S-243, S-420, S-431, S-386, S-611, S-647, S-651, S-653, S-656, S-693, S-954, and EPE-50 (all manufactured by AGC Thane Chemical Co., Ltd.); Examples include U-104, U-201, U-134, U-116 and U-168 (all manufactured by Unichem Co., Ltd.).

[0090] In the composition of the present disclosure, the content of the leveling agent is not particularly limited. When the composition of the present disclosure contains the leveling agent, the content of the leveling agent is preferably set to 100 parts by mass of the curable component, from the viewpoint of facilitating the formation of a cured film having excellent flexibility. It is preferably 0.01 parts by mass or more and 5 parts by mass or less, More preferably, the content is 0.1 parts by mass or more and 3 parts by mass or less. It is more preferable that the content is 0.3 part by mass or more and 1 part by mass or less.

[0091] When the composition of the present disclosure contains the leveling agent, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the leveling agent is, per 100 parts by mass of the solid content of the composition, It is preferably 0.01 parts by mass or more and 5 parts by mass or less, More preferably, the content is 0.1 parts by mass or more and 3 parts by mass or less. It is more preferable that the content is 0.3 part by mass or more and 1 part by mass or less.

[0092] When the composition of the present disclosure contains the leveling agent, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, the content of the leveling agent per 100 parts by mass of the composition is It is preferably 0.01 parts by mass or more and 5 parts by mass or less, More preferably, the content is 0.05 parts by mass or more and 3 parts by mass or less. It is more preferable that the content is 0.08 part by mass or more and 1 part by mass or less.

[0093] B5. Solvent The composition of the present disclosure may contain a solvent for dissolving the compound represented by the general formula (1) above, the other components described above, the polymerization initiator, and the like. The solvent does not fall under any of the compounds represented by the general formula (1), the other curable components, and the polymerization initiators, and examples of the solvent include those that are liquid under atmospheric conditions at 25° C. and can disperse or dissolve each component in the composition. The solvent is preferably one that does not react with the compounds represented by the general formula (1) or other curable components, since it has little adverse effect on the cured film of the composition of the present disclosure. Examples of the solvent include those described in International Publication No. WO2019 / 159953. In the present disclosure, a solvent may be used alone, or a mixed solvent of two or more solvents may be used.

[0094] When the composition of the present disclosure contains a solvent, the content of the solvent is not particularly limited. However, from the viewpoint of facilitating the formation of a cured film having excellent flexibility, when the composition of the present disclosure contains the solvent, the content of the solvent is preferably, per 100 parts by mass of the composition, It is preferably 10 parts by mass or more and 90 parts by mass or less, More preferably, the content is 15 parts by mass or more and 80 parts by mass or less, It is more preferably 20 parts by mass or more and 70 parts by mass or less.

[0095] B6. Other ingredients The composition of the present disclosure contains the above-mentioned polymerization initiator and the above-mentioned curable component, and may further contain other components as necessary. The other components mentioned above include various additives such as stabilizers, inorganic particles, fillers, coupling agents, sensitizers, curing accelerators, colorants such as pigments and dyes, defoamers, thickeners, thixotropic agents, surfactants, flame retardants, plasticizers, antioxidants, polymerization inhibitors, ultraviolet absorbers, antistatic agents, flow adjusters, and adhesion promoters.

[0096] B7. Method for producing the composition The method for producing the composition of the present disclosure is not particularly limited as long as it is a method capable of forming a composition containing the above-mentioned components in desired amounts, and may include a method using a known mixing means.For example, the composition of the present invention can be produced by mixing each component using a mixer such as a homodisper, homomixer, universal mixer, planetary mixer, kneader, or three-roll mixer.

[0097] B8. Use of the composition Applications of the composition of the present disclosure are not particularly limited, and include, for example, optical materials such as glasses and imaging lenses; paints; various coating materials; lining agents; inks; resists; liquid resists; adhesives; sealants for liquid crystal dropping methods; image forming materials; pattern forming materials; printing plates; insulating varnishes; insulating sheets; laminates; printed circuit boards; sealants for semiconductor devices, LED packages, liquid crystal injection ports, organic EL, optical elements, electrical insulation, electronic components, separation membranes, and the like; molding materials; putties; building materials; siding; glass fiber impregnation agents; fillers; passivation films for semiconductors, solar cells, and the like; interlayer insulating films; protective films; prism lenses used in the backlights of liquid crystal display devices. Examples of such materials include lenses sheets; Fresnel lens sheets used in screens of projection televisions and the like; lens portions of lens sheets such as lenticular lens sheets; and backlights using such sheets; protective films and spacers for liquid crystal color filters; DNA separation chips; microreactors; nanobiodevices; recording materials for hard disks; solid-state imaging elements; solar cell panels; light-emitting diodes; organic light-emitting devices; luminescent films; fluorescent films; MEMS elements; actuators; holograms; plasmon devices; polarizing plates; polarizing films; optical lenses such as microlenses; optical elements; optical connectors; optical waveguides; and casting agents for optical modeling.

[0098] C. Cured film Next, the cured film of the present disclosure will be described. The cured film of the present disclosure is a film obtained by curing the above-mentioned composition. According to the present disclosure, a cured film having excellent flexibility can be provided. The composition of the cured film of the present disclosure can be the same as that described in the above section "B. Composition," and therefore a description thereof will be omitted here. The method for producing the cured film of the present disclosure will be described later in "D. Method for producing the cured film."

[0099] D. Method of manufacturing the cured film The method for producing a cured film according to the present disclosure is characterized by having a curing step of irradiating the above-mentioned composition with active energy rays.

[0100] D1.Curing process This step is a step of curing the above-mentioned composition. In this step, any method may be used as long as it can polymerize at least one of the compound represented by general formula (1) and other curable components in the above-mentioned composition. For example, a method of polymerizing the coating film formed by applying the above-mentioned composition by irradiating it with active energy rays may be used.

[0101] Examples of the light source of the active energy ray include electromagnetic wave energy having a wavelength of 2,000 angstroms or more and 7,000 angstroms or less, which is obtained from ultra-high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, mercury vapor arc lamps, xenon arc lamps, carbon arc lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light emitting diodes, CRT light sources, and the like; and high energy rays such as electron beams, X-rays, and radiation. In this step, the light source is preferably an ultra-high pressure mercury lamp, a mercury vapor arc lamp, a carbon arc lamp, a xenon arc lamp, a light emitting diode, or the like, which emits light with a wavelength of 300 to 450 nm, because this makes it easier to control the reaction for curing the composition.

[0102] The amount of irradiation with the active energy rays is not particularly limited, and can be appropriately determined depending on the composition of the composition. The above-mentioned irradiation amount is set to 100 mJ / cm at 365 nm from the viewpoint of preventing deterioration of the composition of the present disclosure. 2 More than 2,000mJ / cm2 It is preferable that:

[0103] In this step, the curing method may be any method that includes a method of irradiating with active energy rays, and a method of heating may be used in combination.

[0104] Examples of the heating method include a method using a hot plate or other hot plate, an atmospheric oven, an inert gas oven, a vacuum oven, and a hot air circulation oven.

[0105] The temperature to which the composition of the present disclosure is heated is not particularly limited, but from the viewpoint of easily controlling the curing reaction of the composition of the present disclosure, the temperature is preferably 50° C. or higher and 200° C. or lower, and more preferably 60° C. or higher and 120° C. or lower. The heating time of the coating film is not particularly limited, but from the viewpoint of improving productivity, It is preferable that the time is 1 second or more and 60 minutes or less. More preferably, the time is 5 seconds or more and 30 minutes or less. It is more preferable that the time is from 10 seconds to 10 minutes.

[0106] D2. Other processes In the present disclosure, other steps may be included as necessary. The other steps include, for example, a coating step of coating the composition of the present disclosure onto a substrate.

[0107] (1) Coating process In the coating step, the composition of the present disclosure can be applied to a substrate by any known method, such as using a spin coater, roll coater, bar coater, die coater, curtain coater, various printing methods, and dipping. The substrate can be appropriately selected depending on the application of the cured film of the present disclosure, and is not particularly limited, and any substrate that is commonly used can be used. Examples of the substrate include metal materials, polymeric materials, wood materials, paper materials, and inorganic materials.

[0108] Examples of the metal material include iron, copper, aluminum, titanium, tinplate, stainless steel, mild steel, plated steel, painted steel sheet, and galvanized steel sheet.

[0109] Examples of the polymeric material include cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, and nitrocellulose; polyamide (nylon); polyurethane; epoxy resin; polycarbonate; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; polystyrene. Examples of suitable resins include styrene-based resins such as styrene and ABS resins; olefin-based resins such as polyethylene, polypropylene, and polymethylpentene; vinyl-based resins such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; acrylic-based resins such as polymethyl methacrylate and polyacrylate; polycarbonate; engineering plastics such as amorphous polyarylate, polysulfone, polyethersulfone, polyphenylene sulfide, polyether ether ketone, polyimide, polyetherimide, and fluororesin; and cyclic polymers such as norbornene resins and cycloolefin polymers (COP).

[0110] Examples of the wood material include wood, plywood, particle board, and MDF.

[0111] Examples of the paper material include plain paper, reinforced paper, resin-impregnated paper, and cardboard.

[0112] Examples of the inorganic material include gypsum board and calcium silicate board. EXAMPLES

[0113] The present invention will be described in more detail below with reference to examples, but the scope of the present invention is not limited to these examples.

[0114] [Example 1] Preparation of Compound No. 13 Compound No. 13 was synthesized according to the following reaction diagram.

[0115] [ka]

[0116] (1) Preparation of Intermediate 1 27.09g (0.19 mol) of acryloylmorpholine, 342.00g of o-xylene and 59.30g (0.58 mol) of alumina were added to a reaction flask and stirred under ice cooling. Next, a mixture of 30.00g (0.29 mol) of diethylenetriamine and 100.00g of o-xylene was added dropwise, heated to 50°C and stirred for 3 hours. After stirring, the alumina was removed and the solvent was distilled off under reduced pressure using an evaporator to obtain intermediate 1.

[0117] (2) Preparation of Compound No. 13 The obtained intermediate 1 was dissolved in 702.09 g of methylene chloride, and 48% by mass of sodium hydroxide aqueous solution 48.94 g (0.59 mol) and ion-exchanged water 72.43 g were added, and the mixture was cooled under ice cooling and stirred. Next, 51.59 g (0.57 mol) of acrylic acid chloride was added dropwise over 30 minutes while keeping the internal temperature below 10°C, and stirred for 2 hours. After stirring, the oil and water were separated, and the organic layer was washed with saturated sodium carbonate aqueous solution, dried with magnesium sulfate, concentrated using an evaporator, and purified by silica gel column chromatography (developing solution = chloroform:methanol = 9:1) to obtain compound No. 13 (yield 26.9%, yield 18.9 g). The obtained compound was analyzed by LC-MS and NMR, and the structure of the target compound No. 13 was identified (MS spectrum 407.28).

[0118] (Analysis results) 1H-NMR (DMSO, 400MHz): δ=8.26(t,1H);6.66-6.82(m,2H);6.09-6.17(m,4H); 5.58-5.68(m,3H);3.43-3.54(m,16H);3.26-3.29(m,2H);2.53-2.61(m,2H)

[0119] [Example 2] Preparation of Compound No. 8 Compound No. 8 was synthesized according to the following reaction diagram.

[0120] [ka]

[0121] (1) Preparation of Intermediate 2 24.41g (0.19 mol) of diethylacrylamide, 342.10g of o-xylene and 59.30g (0.58 mol) of alumina were added to a reaction flask and stirred under ice cooling. Next, a mixture of 30.00g (0.29 mol) of diethylenetriamine and 100.00g of o-xylene was added dropwise, and the mixture was heated to 80°C and stirred for 15 hours. After stirring, the alumina was removed, and the solvent was distilled off under reduced pressure using an evaporator to obtain intermediate 2.

[0122] (2) Preparation of Compound No. 8 The obtained intermediate 2 was dissolved in 677.94 g of methylene chloride, and 48.94 g (0.59 mol) of 48% aqueous sodium hydroxide solution and 72.43 g of ion-exchanged water were added, and the mixture was cooled under ice cooling and stirred. Next, 51.59 g (0.57 mol) of acrylic acid chloride was added dropwise over 30 minutes while maintaining the internal temperature at 10°C or less, and stirred for 2 hours. After stirring, the oil and water were separated, and the organic layer was washed with saturated aqueous sodium carbonate solution, dried over magnesium sulfate, concentrated using an evaporator, and purified by silica gel column chromatography (developing solution = chloroform:methanol = 9:1) to obtain compound No. 8 (yield 22.7%, yield 15.4 g). The obtained compound was analyzed by LC-MS and NMR, and the structure of the target compound No. 8 was identified (MS spectrum 393.30).

[0123] (Analysis results) 1 H-NMR (DMSO, 400MHz): δ=8.26(t,1H);6.59-6.72(m,2H);6.09-6.24(m,4H);5.58-5. 67(m,3H);3.43-3.52(m,8H);3.25-3.27(m,6H);2.53-2.54(m,2H);1.01-1.08(t,6H)

[0124] [Example 3] Preparation of Compound No. 11 Compound No. 11 was synthesized according to the following reaction scheme.

[0125] [ka]

[0126] (1) Preparation of Intermediate 3 27.02g (0.19 mol) of acrylic morpholine, 208.18g of o-xylene and 59.14g (0.58 mol) of alumina were added to a reaction flask and stirred under ice cooling. Next, a mixture of 17.43g (0.29 mol) of ethylenediamine and 100.00g of o-xylene was added dropwise, heated to 50°C and stirred for 3 hours. After stirring, the alumina was removed and the solvent was distilled off under reduced pressure using an evaporator to obtain intermediate 3.

[0127] (2) Preparation of Compound No. 11 The obtained intermediate 3 was dissolved in 532.92 g of methylene chloride, and 34.45 g (0.41 mol) of 48% aqueous sodium hydroxide solution and 50.99 g of ion-exchanged water were added, cooled under ice cooling, and stirred. Next, 34.30 g (0.38 mol) of acrylic acid chloride was added dropwise over 30 minutes while maintaining the internal temperature at 10°C or less, and stirred for 2 hours. After stirring, the oil and water were separated, and the organic layer was washed with saturated aqueous sodium carbonate solution, dried over magnesium sulfate, concentrated using an evaporator, and purified by silica gel column chromatography (developing solution = chloroform:methanol = 95:5) to obtain compound No. 11 (yield 55.8%, yield 29.7 g). The obtained compound was analyzed by LC-MS and NMR, and the structure of the target compound No. 11 was identified (MS spectrum 310.17).

[0128] (Analysis results) 1 H-NMR (DMSO, 400MHz): δ=8.26(t,1H);6.68-6.74(m,1H);6.05-6.20(m,3H); 5.58-5.66(m,2H);3.42-3.60(m,12H);3.17-3.29(m,2H);2.56-2.60(m,2H)

[0129] [Example 4] Preparation of Compound No. 2 Compound No. 2 was synthesized according to the following reaction diagram.

[0130] [ka]

[0131] (1) Preparation of Intermediate 4 24.34g (0.19 mol) of diethylacrylamide, 186.78g of o-xylene and 59.14g (0.58 mol) of alumina were added to a reaction flask and stirred under ice cooling. Next, a mixture of 17.43g (0.29 mol) of ethylenediamine and 100.00g of o-xylene was added dropwise, and the mixture was heated to 50°C and stirred for 4 hours. After stirring, the alumina was removed, and the solvent was distilled off under reduced pressure using an evaporator to obtain intermediate 4.

[0132] (2) Preparation of Compound No. 2 The obtained intermediate 4 was dissolved in 508.82 g of methylene chloride, and 34.45 g (0.41 mol) of 48% aqueous sodium hydroxide solution and 50.99 g of ion-exchanged water were added, cooled under ice cooling, and stirred. Next, 34.30 g (0.38 mol) of acrylic acid chloride was added dropwise over 30 minutes while maintaining the internal temperature at 10°C or less, and stirred for 2 hours. After stirring, the oil and water were separated, and the organic layer was washed with saturated aqueous sodium carbonate solution, dried over magnesium sulfate, concentrated using an evaporator, and purified by silica gel column chromatography (developing solution = chloroform:methanol = 95:5) to obtain compound No. 2 (yield 65.9%, yield 33.5 g). The obtained compound was analyzed by LC-MS and NMR, and the structure of the target compound No. 2 was identified (MS spectrum 256.18).

[0133] (Analysis results) 1 H-NMR (DMSO, 400MHz): δ=8.27(t,1H);6.68-6.79(m,1H);6.05-6.10(m,3H);5.68- 5.69(m,2H);3.39-3.60(m,4H);3.27(m,6H);2.53-2.61(m,2H);1.01-1.08(t,6H)

[0134] [Examples 5 to 18 and Comparative Examples 1 to 10] (Preparation of Curable Composition) The components were mixed according to the formulations shown in Tables 1 and 2 below to obtain curable compositions. The amounts in the tables indicate parts by mass of each component. Each component used is shown below.

[0135] (1) A compound represented by the above general formula (1) A-1: No. 13 (acrylic equivalent 135, molecular weight 406.48) A-2: No. 8 (acrylic equivalent 131, molecular weight 392.50) A-3: No. 11 (acrylic equivalent 155, molecular weight 309.37) A-4: No.2 (acrylic equivalent 148, molecular weight 295.38) a-1: Comparative compound 1 described below (acrylic equivalent: 91, molecular weight: 265.31) a-2: Comparative compound 2 described below (acrylic equivalent: 88, molecular weight: 362.43)

[0136] [ka]

[0137] (2) Other hardening components B-1: N-(2-hydroxyethyl)acrylamide B-2: 4-Acryloylmorpholine

[0138] (3) Polymerization initiator C-1: Ominirad (registered trademark) 2959 (manufactured by IGM Resins BV, compound represented by B32 below, photoradical polymerization initiator, acetophenone-based compound)

[0139] [ka]

[0140] (4) Leveling agent D-1: Surflon (registered trademark) S-386 (manufactured by AGC Seimi Chemical Co., Ltd.)

[0141] (5) Solvent E-1: Water

[0142] (Preparation of cured film) The obtained curable composition was applied to a 100 μm thick PET film (treated for easy adhesion) using a bar coater so that the coating layer was 5 μm thick to form a coating film. The coating film was dried at 80° C. for 2 minutes. Next, a high-pressure mercury lamp was used to irradiate the film with an accumulated light amount of 350 mJ / cm in the atmosphere. 2 , irradiation intensity is 350mW / cm 2 The film was conveyed at a speed of 6 m / min while being irradiated under the conditions of 100° C. to 400° C., and the coating was cured to form a cured film. The obtained cured film was evaluated as follows.

[0143] <Adhesion> The adhesion of the cured film to the substrate was evaluated in accordance with JIS K5600-5-6: Adhesion (cross-cut method). The cured film was cut into 100 squares using a cutter guide with a gap of 1 mm. An adhesive tape (CT-18, manufactured by Nichiban Co., Ltd.) was attached to the cut cured film, and the adhesive tape was then peeled off at an angle of about 60° to the peeling direction. The state of the squares where peeling occurred in the cured film was observed, and the adhesion was evaluated according to the following criteria. The results are shown in Tables 1 and 2 below.

[0144] (Adhesion Evaluation Criteria) 0: The edges of the cut are completely smooth and there are no peeling marks on any of the grids. 1: There is minor spalling of the cured film at the intersection of the cuts, but less than 5% of the cross-cut area is affected. 2: The cured film is delaminated along the edges of the cuts and / or at the intersections. More than 5% but less than 15% of the cross-cut area is affected. 3: The hardened film is partially or completely removed along the edges of the cuts and / or some squares are partially removed but not the entirety of any one square. More than 15% but less than 35% of the cross-cut area is affected. 4: The hardened film is partially or completely removed along the edges of the cuts and / or completely removed in several squares. Less than 35% of the cross-cut area is affected. 5: Peeling is so significant that it cannot be classified as category 4.

[0145] <Bending test> The obtained cured film was cut into a rectangle of 15 mm × 150 mm to prepare a sample. A bending test was carried out on the obtained sample using a planar body no-load U-shaped stretch tester (manufactured by Yuasa System Co., Ltd.) according to the following procedure. Bending jigs were attached to both ends of the short sides of the sample, and the sample was fixed to the testing machine in a horizontally stretched state. Note that the sample was not fixed at any other points than the ends. The test consisted of moving one of the bending jigs, with its short sides fixed, horizontally to a position 12 mm away from the other bending jig and then returning it to its original position, with one cycle being defined as 60 cycles per minute, and 100,000 cycles being performed. When the bending jig approaches to a distance of 6 mm, the center of the sample drops and is bent, and when the bending jig returns to its original position, the sample is stretched horizontally. In this test, the flexibility of the sample can be evaluated by repeatedly bending and horizontally positioning the sample and observing whether scratches are produced on the surface of the sample. After the test, the surface condition of the samples was observed and evaluated according to the following criteria. The results are shown in Tables 1 and 2 below.

[0146] (Evaluation criteria for bending test) +: The sample surface is free of scratches. -: One scratch occurred on the surface of the sample. --: Two or more scratches occurred on the surface of the sample.

[0147] <Pencil hardness> The pencil hardness of the cured film was evaluated in accordance with JIS K5600-5-4 (scratch hardness (pencil method)). Using a Tribogear tester (HHS-2000, manufactured by Shinto Chemical Co., Ltd.), the test was repeated under the conditions of a load of 750 g, a feed scale of 10 mm, and a speed of 1 mm / sec, changing the pencil hardness from 6B to 6H by one rank at a time until scratches were formed on the cured film, and the pencil hardness of the cured film was evaluated by the hardness of the pencil used immediately before scratches were formed on the cured film. The results are shown in Tables 1 and 2 below.

[0148] [Table 1]

[0149] [Table 2]

[0150] It was confirmed that the cured film formed using the composition of the present disclosure has excellent flexibility by comparing Examples 5 to 18 with Comparative Examples 1 to 10. In particular, the composition of the present disclosure containing Compound No. 13 of A-1 can form a cured film having a significantly better balance of flexibility, hardness, and adhesion than Examples 5, 9, and 14.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 (R １ and R ２ each independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms or a heteroatom-containing hydrocarbon group; R １ and R ２ may be linked together to form a heterocycle containing a nitrogen atom, R ３ , R ４ and R ５ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X and Y each independently represent a divalent linking group; a represents a number between 1 and 10.

2. R in the general formula (1) １ and R ２ is a saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, or R １ and R ２ The compound according to claim 1 , wherein:

3. A composition comprising the compound of claim 1 and a polymerization initiator.

4. The composition according to claim 3 , wherein the content of the compound represented by the general formula (1) is 1 part by mass or more and 80 parts by mass or less in 100 parts by mass of the composition.

5. A cured film of the composition according to claim 3 or 4.

6. A method for producing a cured film, comprising a curing step of irradiating the composition according to claim 3 or 4 with active energy rays.

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