Composition containing benzoylformic acid amide derivative

Abstract

To provide a composition containing a benzoylformic acid amide derivative. The composition exhibits at least one performance of a photoradical polymerization initiating property, a photoionic polymerization property, and a photosensitizing effect by irradiation with an active energy ray, and can be used for any application of an ink, an inkjet ink, a three dimensional shaping ink, a pressure sensitive adhesive, an adhesive, a sealant, a coating agent, a photosensitive resin, a nail cosmetic, a dental material, and an aqueous composition.SOLUTION: The composition contains a benzoylformic acid amide derivative (A) having a specific structure and a polymerizable compound (B).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a composition containing a benzoylformamide derivative and a polymerizable compound. [Background technology]

[0002] Photopolymerization and photocuring using ultraviolet (UV) and other active energy rays generally involve irradiating a composition containing a photopolymerization initiator with UV light to generate active species such as radicals and ions, which initiate a polymerization reaction and solidify (cure) the liquid composition in a short period of time. This technology is currently used in a wide range of fields, including paints, coatings, pressure-sensitive adhesives, adhesives, elastomer materials, inkjet inks, sealing materials, encapsulants, dental hygiene materials, and optical materials. In particular, because it can be cured in any location and shape, it is increasingly being used in nail cosmetics such as gel nails, and as a material for three-dimensional stereolithography in 3D printers.

[0003] Photopolymerization initiators that generate radicals when exposed to active energy rays can be classified into intramolecular cleavage type and hydrogen abstraction type. The former is a type that generates radicals by intramolecular cleavage, while the latter is a type that generates radicals by abstracting hydrogen from a hydrogen donor. Intramolecular cleavage types leave decomposition products derived from the initiator in the cured product, which can cause problems such as reduced durability of the cured product, odor generation, and coloring over time, as well as low safety. Hydrogen abstraction types often have low photopolymerization initiation efficiency, but they have been attracting attention in recent years because they do not produce decomposition products derived from the initiator.

[0004] Furthermore, due to their high safety, the use of long-wavelength UV-LED lamps and LED lamps has become widespread. Although active development has been conducted on photopolymerization initiators and photosensitizers that can be used with these light sources, there have been issues with their low photopolymerization initiation and photosensitization effects, and the resulting cured products tending to yellow. Summary of the Invention [Problem to be solved by the invention]

[0005] The first object of the present invention is to provide a benzoyl formic acid amide derivative. The benzoyl formic acid amide derivative has high photopolymerization initiation properties with respect to actinic radiation, particularly light of 360 to 420 nm emitted by an LED lamp. The resulting cured product contains no decomposition products of the benzoyl formic acid amide derivative. The second object of the present invention is to provide the benzoyl formic acid amide derivative as a highly safe photopolymerization initiator. The third object of the present invention is to provide a highly curable actinic radiation-curable composition containing the benzoyl formic acid amide derivative as a photopolymerization initiator. The fourth object of the present invention is to provide a highly safe ink composition, inkjet ink composition, ink composition for three-dimensional modeling, pressure-sensitive adhesive composition, adhesive composition, sealant composition, photosensitive composition, nail cosmetic composition, dental material composition, coating composition, aqueous composition, hydrogel composition, or intraocular implant material composition, which contains the benzoyl formic acid amide derivative and has high compatibility, excellent adhesion to substrates, and produces cured products with minimal yellowing and bleed-out over time.

[0006] The benzoyl formic acid amide derivative has photosensitivity to actinic radiation, particularly light of 360 to 420 nm emitted by an LED lamp, and can be used as a photosensitizer to produce cured products that do not yellow. The fifth objective is to provide a benzoyl formic acid amide derivative. The sixth objective is to provide an actinic radiation-curable composition containing the benzoyl formic acid amide derivative as a photosensitizer, which has high curability and compatibility. The seventh objective is to provide an ink composition, inkjet ink composition, ink composition for three-dimensional modeling, pressure-sensitive adhesive composition, adhesive composition, sealant composition, photosensitive composition, nail cosmetic composition, dental material composition, coating composition, aqueous composition, hydrogel composition, or intraocular implant material composition, which contains the benzoyl formic acid amide derivative and can produce cured products that have excellent adhesion to substrates and excellent durability with minimal yellowing over time. [Means for solving the problem]

[0007] As a result of extensive research, the present inventors have found a benzoylformamide derivative having a benzoylformamide group represented by general formula (1), and have arrived at the present invention. JPEG2026031575000001.jpg3364Q 1 ~Q 3 each independently represents a hydrogen atom, a substituent represented by any of the formulae (Chemical Formula 2) to (Chemical Formula 8), a halogen group, or a nitrile group, and is bonded to any of the 2- to 6-positions. JPEG2026031575000002.jpg11539R 1 ~R 10 each independently represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, or a cyclic alkenyl group having 3 to 18 carbon atoms; * indicates the binding position. [Effects of the Invention]

[0008] The benzoyl formic acid amide derivatives disclosed herein exhibit high initiation efficiency (also referred to as polymerization initiation or photoinitiation) with long-wavelength light in the 360-420 nm range, including light irradiated from LED lamps with wavelengths of, for example, 365 nm, 385 nm, 395 nm, and 405 nm. The simultaneously generated radicals are highly active, making them suitable for use as photopolymerization initiators. Active energy ray-curable compositions containing the benzoyl formic acid amide derivatives as photopolymerization initiators can easily produce fully cured products with low energy (low cumulative light dose) and high speed (short curing time), even in industrial production environments under air, without the need for additives such as hydrogen donors (co-initiators), general-purpose photosensitizers, or curing accelerators. Furthermore, the resulting cured products are free of decomposition products of the benzoyl formic acid amide derivatives used as photopolymerization initiators, exhibit low odor, yellowing over time, and bleed-out, and are highly durable and safe. The benzoylformamide derivative can be suitably used in a wide variety of applications, such as actinic ray-curable ink compositions, inkjet ink compositions, ink compositions for three-dimensional modeling, pressure-sensitive adhesive compositions, adhesive compositions, sealant compositions, photosensitive compositions, nail cosmetic compositions, dental material compositions, coating compositions, aqueous compositions, hydrogel compositions, and intraocular implant material compositions.

[0009] The benzoyl formic acid amide derivatives disclosed herein exhibit a photosensitizing effect on other commonly used photoradical polymerization initiators and photoionic polymerization initiators when absorbing long-wavelength light in the 360-420 nm range or light emitted from LED lamps at 365 nm, 385 nm, 395 nm, and 405 nm, making them suitable for use as photosensitizers that are resistant to yellowing upon photocuring. Active energy ray-curable compositions containing the benzoyl formic acid amide derivatives as photosensitizers can be used in combination with photopolymerization initiators that are poorly cured by long-wavelength light in the 360-420 nm range or light emitted from LED lamps at 365 nm, 385 nm, 395 nm, and 405 nm, making it easy to obtain fully cured products with low energy (low cumulative light dose) and high speed (short curing time), even in industrial production environments under air. Furthermore, the resulting cured products exhibit low odor, yellowing over time, and bleed-out, and are highly durable and safe. The benzoylformamide derivative can be suitably used in a wide variety of applications, such as actinic ray-curable ink compositions, inkjet ink compositions, ink compositions for three-dimensional modeling, pressure-sensitive adhesive compositions, adhesive compositions, sealant compositions, photosensitive compositions, nail cosmetic compositions, dental material compositions, coating compositions, aqueous compositions, hydrogel compositions, and intraocular implant material compositions. DETAILED DESCRIPTION OF THE INVENTION

[0010] Hereinafter, embodiments of the present disclosure will be described in detail, but the scope of the present invention is not limited to the embodiments described herein, and various modifications can be made without departing from the spirit of the present invention. Furthermore, when multiple upper and lower limit values ​​are specified for a specific parameter, any upper and lower limit values ​​can be combined to form a suitable numerical range.

[0011] One embodiment of the present disclosure is a benzoylformamide derivative (D) having one or more benzoylformamide groups represented by general formula (1) in the molecule.

[0012] Q in general formula (1) 1 ~Q 3are each independently a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, an alkoxy group having a cyclic alkenyl group having 3 to 18 carbon atoms, an amino group, an alkylamino group, a dialkylamino group, an alkoxycarbonyl group, an alkyl ester group, an aminocarbonyl group, an alkylaminocarbonyl group, a dialkylaminocarbonyl group, an alkylamide group, a halogen group, or a nitrile group. 1 ~Q 3 Q is bonded to any position from 2 to 6 of the benzene ring. 1 ~Q 3 When Q is a hydrogen atom, the benzoyl formic acid amide derivative (D) exhibits good photopolymerization initiation and photosensitization properties when exposed to a high-pressure mercury lamp and a UV-LED light source of 360 nm to 410 nm, and exhibits little coloring upon exposure to light. 1 ~Q 3 When Q is an electron-donating alkyl group, alkoxy group, amino group, alkylamino group, dialkylamino group, alkyl ester group, or alkylamide group, the absorption wavelength of the benzoylformamide derivative (D) shifts to the long wavelength side, and the sensitivity to light sources of 390 nm to 420 nm is high, so that the derivative is more suitably used as both a photopolymerization initiator and a photosensitizer. These electron-donating substituents may become discolored by light irradiation, but from the viewpoint of keeping the discoloration of D at a practically low level, Q 1 ~Q 3 is particularly preferably an alkoxy group or an alkyl ester group.

[0013] The benzoylformamide group of the benzoylformamide derivative (D) is a monosubstituted or disubstituted amide group of benzoylformic acid. Both the monosubstituted benzoylformamide group and the disubstituted benzoylformamide group have photopolymerization initiation and photosensitization properties, with the monosubstituted benzoylformamide group exhibiting higher photopolymerization initiation properties. The monosubstituted benzoylformamide group has a hydrogen atom bonded to its nitrogen atom, making it a hydrogen-abstraction-type photoinitiating functional group, but it also functions as a hydrogen-donating group, efficiently generating active radicals through intramolecular and / or intermolecular hydrogen abstraction. Therefore, D having the monosubstituted benzoylformamide group exhibits high photopolymerization initiation properties and polymerization initiation properties against highly safe ultraviolet light in the 360-420 nm wavelength range, even without the use of an amine hydrogen donor, which is prone to coloration.

[0014] The benzoylformamide derivative (D) of the present disclosure is preferably at least one compound represented by any one of general formulas (2) to (4).

[0015] JPEG2026031575000003.jpg3564In formula, Q 1 ~Q 3 is the same as defined in general formula (1), B 1 represents a monovalent organic group which may have a hydrogen atom, a hydroxyl group, an amino group, a thiol group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, an imide group, an ethylenically unsaturated group, or a benzoylformamide group; B 2 represents a monovalent organic group which may have a hydroxyl group, an amino group, a thiol group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, an imide group, an ethylenically unsaturated group, or a benzoylformamide group.

[0016] JPEG2026031575000004.jpg3677In formula, Q 1 ~Q 3 is the same as defined in general formula (1), B 3 represents an m-valent organic group which may have an ethylenically unsaturated group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group, or an imide group, R 11 represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a cyclic alkenyl group having 3 to 18 carbon atoms, or an aryl group having 6 to 8 carbon atoms; R 12 represents a linear saturated divalent hydrocarbon group having 1 to 18 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 18 carbon atoms, a branched saturated or unsaturated divalent hydrocarbon group having 3 to 18 carbon atoms, an alicyclic saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a divalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group, m represents an integer of 1 to 10.

[0017] JPEG2026031575000005.jpg4283In formula, Q 1 ~Q 3 is the same as defined in general formula (1), A 1 represents a divalent organic group which may have an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, or an imide group, B 4 , B 5 may each independently have an ethylenically unsaturated group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group or an imide group, and B 4 , B 5 represents a monovalent organic group containing one or more ethylenically unsaturated bonds, R 13represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a cyclic alkenyl group having 3 to 18 carbon atoms, or an aryl group having 6 to 8 carbon atoms; R 14 represents a linear saturated trivalent hydrocarbon group having 1 to 8 carbon atoms, a linear unsaturated trivalent hydrocarbon group having 2 to 8 carbon atoms, a branched saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, an alicyclic saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, a trivalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a trivalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group; R 15 represents a linear saturated divalent hydrocarbon group having 1 to 18 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 18 carbon atoms, a branched saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, an alicyclic saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a divalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group; n represents an integer of 1 to 100.

[0018] When the benzoylformamide derivative (D) is represented by the general formula (2), the benzoylformamide group has a hydrophobic benzene ring and a hydrophilic formic acid amide group, and is amphiphilic. 1 and B 2 By adjusting the polarity of B (which are independent of each other) according to the purpose, D has high compatibility with other components used in the curable composition, and the transparency of the resulting curable composition and the cured product obtained by curing it is high. 1 and / or B 2 It is preferable that B has an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group, or an imide group, since this makes it easier to adjust the polarity. 1 and B2 More preferably, B has an ether group, an ester group, a urethane group, or an amide group. 1 When is a hydrogen atom, D has a benzoylformic acid mono-substituted amide group, and photopolymerization initiation is higher, which is more preferable.

[0019] B 1 and B 2 may further have a benzoylformamide group represented by general formula (1). In this case, the benzoylformamide derivative (D) has multiple benzoylformamide groups, which is preferable because it has higher photopolymerization initiation ability and photosensitization ability. The benzoylformamide groups contained in D may be the same or different.

[0020] The benzoylformamide derivative (D) represented by the general formula (2) can be used as a photosensitizer for photoionic polymerization. 1 and B 2 It is preferable that D has a cyclic ether group, because D is incorporated into the cured product via a covalent bond by photoionic polymerization. The compound may have one or more cyclic ether groups.

[0021] B 1 and B 2 It is preferable that the benzoyl formic acid amide derivative (D) further has an ethylenically unsaturated group. In this case, the benzoyl formic acid amide derivative (D) is preferably used as a photopolymerization initiator or photosensitizer having an ethylenically unsaturated group, because D is incorporated into the cured product via a covalent bond by photoradical polymerization. It is preferable that the benzoyl formic acid amide derivative (D) has one or more ethylenically unsaturated groups, and more preferably has two or more ethylenically unsaturated groups. The ethylenically unsaturated group may be of one type or of multiple types.

[0022] B 1 and B 2When (D) has a urethane group, the benzoylformamide derivative (D) has good compatibility with other components used in the curable composition, and the resulting curable composition and its cured product have high transparency. The ratio of the number (total) of urethane groups to the number (total) of benzoylformamide groups in D is preferably 0.1 or more, more preferably 0.5 or more. Furthermore, as the number of urethane groups increases, the viscosity of D increases, and therefore the ratio is preferably 10.0 or less.

[0023] It is more preferable that the benzoylformamide derivative (D) has a urethane group represented by general formula (3) or (4). The urethane group has a hydrogen atom bonded to its nitrogen atom and can function as a hydrogen donor group, and D has good photopolymerization initiation properties against highly safe ultraviolet light of 360 to 420 nm.

[0024] When the benzoylformamide derivative (D) has one or more urethane groups, the number of atoms directly linked between the nitrogen atom of the benzoylformamide group and the nitrogen atom of the urethane group nearest thereto is preferably 3 to 20. When the number of directly linked atoms is 3 or more, the interaction between the benzoylformamide group and the urethane group improves both the hydrogen abstraction ability of the benzoylformamide group and the hydrogen donating ability of the urethane group. Furthermore, when the number of directly linked atoms is 20 or less, the benzoylformamide group and the urethane group in the molecule are easily close to each other, facilitating a hydrogen abstraction reaction. From these viewpoints, the number of directly linked atoms is more preferably 4 to 10, and even more preferably 4 to 6.

[0025] The benzoylformamide derivative (D) represented by the general formula (3) has one or more benzoylformamide groups and one or more urethane groups in the molecule. The urethane groups have good compatibility with other components used in the curable composition, and the obtained curable composition and its cured product have high transparency. In addition, from the viewpoint of further improving the compatibility of the curable composition, B 3It is preferable that D further has one or more urethane groups. The ratio of the number (total) of urethane groups to the number (total) of benzoylformamide groups in D is preferably 0.5 or more, more preferably 2.0 or more. As the number of urethane groups increases, the viscosity of D increases, and the ratio is preferably 10.0 or less, more preferably 6.0 or less, and particularly preferably 4.0 or less.

[0026] R in general formula (3) 11 R is a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a cyclic alkenyl group having 3 to 18 carbon atoms, or an aryl group having 6 to 8 carbon atoms. 11 is a hydrogen atom, the benzoylformic acid amide derivative (D) has a benzoylformic acid mono-substituted amide group and is therefore more preferred because it has excellent photopolymerization initiation properties.

[0027] R in general formula (3) 12 R is a linear saturated divalent hydrocarbon group having 1 to 18 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 18 carbon atoms, a branched saturated or unsaturated divalent hydrocarbon group having 3 to 18 carbon atoms, an alicyclic saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a divalent organic group in which one or more of the carbon atoms or hydrogen atoms of any of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group. 12 is preferably a linear saturated divalent hydrocarbon group having 1 to 8 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 8 carbon atoms, or a branched saturated or unsaturated divalent hydrocarbon group having 3 to 18 carbon atoms, and more preferably a linear saturated divalent hydrocarbon group having 2 to 4 carbon atoms, or a branched saturated divalent hydrocarbon group having 3 to 8 carbon atoms.

[0028] The benzoyl formate amide group is amphiphilic, and B 3By adjusting the polarity of B according to the purpose, D has high compatibility with other components used in the curable composition, and the transparency of the resulting curable composition and the cured product obtained by curing the same is high. 3 When the copolymer has an ethylenically unsaturated group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group, or an imide group, the polarity can be easily adjusted, which is preferable.

[0029] The benzoylformamide derivative (D) represented by the general formula (3) can also be used as a photosensitizer for photoionic polymerization. 3 It is preferable that D has a cyclic ether group, because D is incorporated into the cured product via a covalent bond by photoionic polymerization. The compound may have one or more cyclic ether groups.

[0030] B 3 It is preferable that the benzoyl formic acid amide derivative (D) further has an ethylenically unsaturated group. In this case, the benzoyl formic acid amide derivative (D) is preferably used as a photopolymerization initiator or photosensitizer having an ethylenically unsaturated group, because D is incorporated into the cured product via a covalent bond by photoradical polymerization. It is preferable that the benzoyl formic acid amide derivative (D) has one or more ethylenically unsaturated groups, and more preferably has two or more ethylenically unsaturated groups. The ethylenically unsaturated group may be of one type or of multiple types.

[0031] In general formula (3), m is an integer of 1 to 10. When m is 1 or more, the benzoylformamide derivative (D) has one or more benzoylformamide groups in its molecule, and can function as both a photopolymerization initiator and a photosensitizer. When m exceeds 10, the molecular weight and viscosity of D become high, which may reduce the handleability of the curable composition containing D, which is undesirable. From these viewpoints, m is more preferably an integer of 2 to 4.

[0032] The benzoylformamide derivative (D) represented by the general formula (3) can be produced by synthesizing benzoylformamide monool by an amidation reaction of benzoylformic acid with an aminoalkyl alcohol, followed by a urethane reaction with an isocyanate compound. Examples of the aminoalkyl alcohol include 4-aminobenzyl alcohol, 2-(2-aminoethoxy)ethanol, 2-aminoethanol, 2-aminopropanol, 2-amino-2-methyl-1-propanol, 2-amino-2-ethyl-1-propanol, 3-aminopropanol, 2-amino-1-butanol, 3-amino-1-butanol, 4-aminobutanol, 5-aminopentanol, 2-amino-1-hexanol, 6-aminohexanol, 7-aminoheptanol, 2-amino-1-octanol, 8-aminooctanol, 2-amino-1-decanol, 10-aminodecanol, 12-aminododecanol, 18-aminooctadecanol is preferred, 2-aminoethanol, 2-aminopropanol, 2-amino-2-methyl-1-propanol, 2-amino-2-ethyl-1-propanol, 3-aminopropanol, 2-amino-1-butanol, 3-amino-1-butanol, 4-aminobutanol, 2-amino-1-hexanol, 7-aminoheptanol, 2-amino-1-octanol, 2-amino-1-decanol, 2-amino-1-dodecanol, and 2-amino-1-octadecanol are more preferred, and 2-aminoethanol, 2-aminopropanol, and 2-amino-2-methyl-1-propanol are even more preferred.

[0033] The benzoylformamide derivative (D) represented by the general formula (4) has one or more benzoylformamide groups, two or more urethane groups, and one or more ethylenically unsaturated groups in the molecule. The urethane groups have good compatibility with other components constituting the curable composition, and the curable composition containing D and the cured product obtained by curing the same have high transparency. From this perspective, A 1 , B 4 and B 5Preferably, one or more of the above further have one or more urethane groups. The ratio of the total number of urethane groups in D to the total number of benzoylformamide groups is preferably 2.0 or more, more preferably 2.5 or more. Furthermore, since the viscosity of D increases as the number of urethane groups increases, the ratio is preferably 15.0 or less, more preferably 8.0 or less, and particularly preferably 5.0 or less.

[0034] R in general formula (4) 13 R is a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a cyclic alkenyl group having 3 to 18 carbon atoms, or an aryl group having 6 to 8 carbon atoms. 13 is a hydrogen atom, the benzoylformic acid amide derivative (D) has a benzoylformic acid mono-substituted amide group and is therefore preferred because it has excellent photopolymerization initiation properties.

[0035] R in general formula (4) 14 is a linear saturated trivalent hydrocarbon group having 1 to 8 carbon atoms, a linear unsaturated trivalent hydrocarbon group having 2 to 8 carbon atoms, a branched saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, an alicyclic saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, a trivalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a trivalent organic group in which any one or more of the carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group. From the viewpoint that the number of atoms directly linked between the nitrogen atom of the benzoylformamide group and the nitrogen atom of the urethane group immediately adjacent to it is preferably 3 to 10, R 14 is preferably a linear saturated trivalent hydrocarbon group having 1 to 8 carbon atoms, a linear unsaturated trivalent hydrocarbon group having 2 to 8 carbon atoms, a branched saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, or an alicyclic saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, and more preferably a linear saturated trivalent hydrocarbon group having 2 to 4 carbon atoms, or a branched saturated trivalent hydrocarbon group having 3 or 4 carbon atoms.

[0036] R in general formula (4)15 represents a linear saturated divalent hydrocarbon group having 1 to 18 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 18 carbon atoms, a branched saturated or unsaturated divalent hydrocarbon group having 3 to 18 carbon atoms, an alicyclic saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a divalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group. 1 From the viewpoint of ease of introduction of urethane groups bonded to R 15 is preferably an alkylene group having 1 to 18 carbon atoms.

[0037] The benzoylformamide group is amphiphilic, and A 1 By adjusting the polarity of A according to the purpose, D has high compatibility with other components used in the curable composition, and the transparency of the resulting curable composition and the cured product obtained by curing the same is high. 1 It is preferable that A has an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, or an imide group, since this facilitates adjustment of the polarity. 1 When A is an ether group, a thioether group, an ester group, a carbonate group, or a urethane group, the number of these groups can be easily adjusted, and A 1 This is preferable because the polarity of the ions can be more easily adjusted.

[0038] B 4 , B 5 may each independently have an ethylenically unsaturated group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group or an imide group, and B 4 , B 5 Either one or both of the above is a monovalent organic group containing one or more ethylenically unsaturated bonds.

[0039] The benzoylformamide derivative (D) represented by the general formula (4) can also be used as a photosensitizer for photoionic polymerization. 4and / or B 5 It is preferable that D has a cyclic ether group, because D is incorporated into the cured product via a covalent bond by photoionic polymerization. The compound may have one or more cyclic ether groups.

[0040] B 4 , B 5 Since either one or both of B and B have one or more ethylenically unsaturated bonds, the benzoyl formic acid amide derivative (D) is incorporated into the cured product via a covalent bond by photoradical polymerization. 4 and B 5 It is preferred that both of them have an ethylenically unsaturated group. The ethylenically unsaturated group may be of one type alone or of multiple types.

[0041] B 4 and B 5 The polarity of B can be adjusted according to the purpose. 4 and B 5 It is preferable that B has an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, or an imide group, since this facilitates adjustment of the polarity. 4 and B 5 When B is an ether group, a thioether group, an ester group, a carbonate group, or a urethane group, the number of these groups can be easily adjusted. 4 and B 5 This is preferable because the polarity of the ions can be more easily adjusted.

[0042] In general formula (4), n is an integer of 1 to 100. When n is 1 or more, the benzoylformamide derivative (D) has one or more benzoylformamide groups and can function as both a photopolymerization initiator and a photosensitizer. When n is 2 or more, both photopolymerization initiation and photosensitization are high, which is preferable. When n exceeds 100, the molecular weight and viscosity of D are high, which may reduce the handleability of the curable composition containing D, which is undesirable. From these viewpoints, n is more preferably an integer of 2 to 50, and particularly preferably an integer of 2 to 20.

[0043] The compound represented by general formula (4) can be produced by synthesizing benzoylformic acid amide diol through an amidation reaction between benzoylformic acid and an aminoalkyl alcohol, followed by a urethane reaction with an isocyanate compound. Examples of aminoalkyl diols include 2-aminoethylene glycol, 2-amino-1,3-propanediol, 3-amino-1,2-propanediol, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol, 2-amino-2-butyl-1,3-propanediol, 2-amino-2-hexyl-1,3-propanediol, and 2-amino-2-octyl-1,3-propanediol. Preferred are 2-amino-2-dodecyl-1,3-propanediol, 2-amino-2-octadecyl-1,3-propanediol, 2-amino-1,4-butanediol, and 2-amino-1,6-hexanediol, and more preferred are 2-amino-1,3-propanediol, 3-amino-1,2-propanediol, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-ethyl-1,3-propanediol.

[0044] The benzoyl formic acid amide derivative (D) is a hydrogen abstraction photopolymerization initiator and does not generate decomposition products upon photopolymerization. Even when used as a photosensitizer, the benzoyl formic acid amide derivative (D) does not generate decomposition products upon photopolymerization. The molecular weight of D is preferably 300 or more, more preferably 500 or more, and particularly preferably 1,000 or more. When the molecular weight of D is 300 or more, the volatility of D is low, the odor of the resulting cured product is low, and bleeding of D from the cured product is unlikely to occur. A higher molecular weight of D is preferable because it is safer; however, if it exceeds 200,000, the viscosity of D and the viscosity of the curable composition containing it may increase significantly, resulting in poor handleability. From these viewpoints, the molecular weight of D is preferably 200,000 or less, more preferably 150,000 or less, and particularly preferably 100,000 or less. In the present invention, compounds with a molecular weight of less than 300 are referred to as low-molecular-weight components. Many low molecular weight components are highly volatile and have low safety. Therefore, if low molecular weight components are present in a cured product, they will bleed out from the cured product over time, causing problems such as a deterioration in the appearance of the cured product and the generation of an odor.

[0045] The benzoyl formic acid amide derivative (D) can be synthesized by the following method. Benzoyl formic acid or a benzoyl formate ester (hereinafter collectively referred to as raw material (a1)) and an amine compound (hereinafter also referred to as an amino group-containing compound, raw material (a2)) are subjected to an amidation reaction to obtain the benzoyl formic acid amide derivative (D) represented by general formula (2). Furthermore, raw material (a2) can have multiple amino groups, or in addition to amino groups, hydroxyl groups, carboxyl groups, urethane groups, urea groups, or amide groups. It is preferable that a2 has a reactive group such as a hydroxyl group, amino group, or carboxyl group. After the amidation reaction of a1 and a2, these reactive groups can be used to further react with various compounds. It is more preferable that the reactive group of a2 is a hydroxyl group. When a2 has a hydroxyl group, after the reaction of a1 and a2 to produce benzoyl formic acid amide, the hydroxyl group can be used to easily carry out etherification reactions, esterification reactions, and urethanization reactions. In the urethane reaction, a compound having an ethylenically unsaturated group, a hydroxyl group, an amino group, a carboxyl group, an isocyanate group, or the like is used as a raw material to synthesize a benzoylformamide derivative (D) represented by general formula (3) or general formula (4).

[0046] Examples of benzoylformic acid or benzoylformic acid ester (a1) include benzoylformic acid, alkyl benzoylformate (a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms) ester, and alkenyl benzoylformate (a linear alkenyl group having 2 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, or a cyclic alkenyl group having 3 to 18 carbon atoms) ester. In addition, the benzoylformic acid, alkyl benzoylformate, or alkenyl benzoylformate of a1 has a substituent bonded to any of the 2- to 6-positions of the benzene ring, as shown in Chemical Formula 2 to Chemical Formula 8. Specifically, methyl benzoylformate, ethyl benzoylformate, methyl 2-methylbenzoylformate, methyl 3-methylbenzoylformate, methyl 4-methylbenzoylformate, ethyl 4-methylbenzoylformate, methyl 4-ethylbenzoylformate, methyl 4-butylbenzoylformate, methyl 4-octylbenzoylformate, methyl 4-dodecylbenzoylformate, methyl 4-octadecylbenzoylformate, methyl 4-ethynylbenzoylformate, methyl 4-ethylbenzoylformate, methyl 2-methoxycarbonylbenzoylformate, methyl 3-methoxycarbonylbenzoylformate, methyl 4-methoxycarbonylbenzoylformate, methyl 3-ethoxycarbonylbenzoylformate, methyl 4-ethoxycarbonylbenzoylformate, methyl 4-butoxycarbonylbenzoylformate, Examples of the alkylbenzoylformate include methyl 4-methoxycarbonylbenzoylformate, methyl 3,5-dimethoxybenzoylformate, methyl 2,4-dimethoxybenzoylformate, methyl 2,4-diethoxybenzoylformate, methyl 2,4-dibutoxybenzoylformate, methyl 3,4,5-trimethoxybenzoylformate, methyl 4-methoxycarbonylbenzoylformate, methyl 4-acetoxybenzoylformate, methyl 4-dimethylaminobenzoylformate, methyl 2-acetamidobenzoylformate, methyl 3-chlorobenzoylformate, methyl 4-chlorobenzoylformate, methyl 3-bromobenzoylformate, methyl 4-bromobenzoylformate, ethyl 3-bromobenzoylformate, ethyl 4-bromobenzoylformate, methyl 4-nitrilebenzoylformate, and ethyl 4-nitrilebenzoylformate. These alkylbenzoylformates may be used singly or in combination.

[0047] The amino group-containing compound (a2) may be an amine compound such as an alkylamine, an alkenylamine, a dialkylamine, a dialkenylamine, an alkylalkenylamine, or an arylamine, an aminoalkyl monool, an aminoalkyl diol, an aminoalkyl triol, an aminoalkyl tetraol, an aminoalkyl pentanol, an N-alkyl-aminoalkyl monool, an N-alkyl-aminoalkyl diol, an N-alkyl-aminoalkyl triol, an N-alkyl-aminoalkyl tetraol, an N-alkyl-aminoalkyl pentanol, an N,N-bis(hydroxyalkyl)amine, an N,N-bis(dihydroxyalkyl)amine, or a hydroxyalkyl amine. Examples of suitable amino group-containing compounds include amine compounds having a hydroxyl group such as alkylarylamines, amine compounds having a thiol group such as aminoalkylthiols and aminoalkenylthiols, amine compounds having an ether group such as (aminoalkoxy)alkanols, dialkylene glycol monoamines, trialkylene glycol monoamines, and polyalkylene glycol monoamines, amine compounds having multiple amino groups such as alkylenediamines, polyalkyleneimines, dialkylene glycol diamines, trialkylene glycol diamines, polyalkylene glycol diamines, and diaminoalkanols, and amine compounds having a carboxyl group such as amino acids and aminobenzoic acid. The alkyl groups are linear alkyl groups having 1 to 18 carbon atoms, branched alkyl groups having 3 to 18 carbon atoms, and cyclic alkyl groups having 3 to 18 carbon atoms, and the alkenyl groups are linear alkylene groups having 2 to 18 carbon atoms, branched alkylene groups having 3 to 18 carbon atoms, and cyclic alkylene groups having 3 to 18 carbon atoms. These amino group-containing compounds may be used alone or in combination of two or more types.

[0048] When the amino group-containing compound (a2) has a hydroxyl group, a carboxyl group, a thiol group, or multiple amino groups, a benzoylformamide derivative (D) having a hydroxyl group, a carboxyl group, a thiol group, or an amino group can be obtained. D can be further subjected to urethanization, thiourethanization, etherification, esterification, urea formation, amidation, or imidization using these reactive groups. Urethanization is the reaction of a hydroxyl group with an isocyanate group; thiourethanization is the reaction of a thiol group with an isocyanate group; etherification is the reaction of a hydroxyl group with an organic halogen; esterification is the reaction of a hydroxyl group with a carboxyl group or a carboxyl group with an epoxy group; urea formation is the reaction of an amino group with an isocyanate group; amidation is the reaction of an amino group with a carboxyl group or a carboxyl group with an isocyanate group; and imidization is the reaction of an amino group with a carboxylic anhydride group. By appropriately selecting and combining raw materials having the various functional groups described above, D represented by general formula (3) and general formula (4) can be synthesized.

[0049] The amidation reaction of benzoylformic acid or benzoylformate ester (a1) with amino group-containing compound (a2) is preferably carried out under light-shielded conditions. Specifically, the reaction may be carried out under light-shielded conditions, in an ultraviolet-blocking environment such as a yellow room, under fluorescent lights that do not irradiate ultraviolet light, or under a red darkroom safelight. The reaction can proceed under mild conditions at atmospheric pressure and 100°C or less. A solvent (c) may be used for the reaction. Examples of the solvent (c) include general-purpose solvents such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, tetrahydrofuran, 1,4-dioxane, chloroform, 1,2-dichloroethane, ethyl acetate, butyl acetate, N,N-dimethylformamide, 3-methoxy-N,N-dimethylpropionamide, 3-butoxy-N,N-dimethylpropionamide, N,N-dimethylpropionamide, dimethylacetamide, dimethyl sulfoxide, 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, etc. Alternatively, a polymerizable compound (radical, cationic, or anionic polymerization by light or heat) that is liquid at the reaction temperature and does not react with the raw materials and products can also be used as the solvent (c). Examples of the polymerizable compound solvent include N-(meth)acroylmorpholine, (meth)acrylic acid esters having a linear alkyl group or alkoxy group having 1 to 18 carbon atoms, a branched or cyclic alkyl group or alkoxy group having 3 to 18 carbon atoms, N-substituted (meth)acrylamide, and N,N-disubstituted (meth)acrylamide.

[0050] When synthesizing a benzoyl formate derivative (D) by the amidation reaction of a benzoyl formate ester (a1) and an amino group-containing compound (a2), alcohol is produced as a by-product, and D containing the alcohol is obtained as a crude product. When a solvent (c) is used, D containing the alcohol and c is obtained as a crude product. These crude products can be used directly in a curable composition, or they can be used in a curable composition after removing the alcohol and c. If the resulting D contains a hydroxyl group, a carboxyl group, a thiol group, or an amino group, these groups can be used to synthesize a new D. In this case, the reaction can be carried out while containing the alcohol and c, or the reaction can be carried out after removing the alcohol and c. Methods for removing the alcohol and c include distillation under atmospheric or reduced pressure, bubbling with dry air or an inert gas such as nitrogen, and freeze-drying.

[0051] A hydroxyl group-containing benzoyl formic acid amide derivative (D) can introduce a urethane group into the D molecule by reacting with an isocyanate compound. An ethylenically unsaturated group can be introduced into D by reacting with an isocyanate compound having an ethylenically unsaturated group. A urethane group and an ethylenically unsaturated group can be introduced into D by reacting with a polyisocyanate compound or a compound having an ethylenically unsaturated group and a hydroxyl group. D can also react with a polyol via a polyisocyanate. By using a polyol having an ether group, a thioether group, an ester group, a carbonate group, a siloxane group, an amide group, or an imide group, these functional groups can be easily introduced into D. Furthermore, a cyclic ether group can be introduced into D by reacting D with a polyisocyanate or a compound having a cyclic ether group and a hydroxyl group. When D having an ethylenically unsaturated group and / or a cyclic ether group is used as a photopolymerization initiator or photosensitizer in a curable composition, D is incorporated into the cured product by photoradical polymerization and / or photoionic polymerization via a chemical bond. In this case, even if the molecular weight of D is less than 300, bleed-out from the cured product does not occur, and D can be suitably used in various applications as both a photopolymerization initiator and a photosensitizer.

[0052] The ethylenically unsaturated group of the benzoyl formic acid amide derivative (D) is one or more groups selected from a (meth)acrylate group, a (meth)acrylamide group, a vinyl group, a vinyl ether group, an alkyl vinyl ether group, an allyl group, a (meth)allyl ether group, a styryl group, and a maleimide group. Furthermore, from the viewpoint of high polymerizability, a (meth)acrylate group or a (meth)acrylamide group is preferred. From the viewpoint of high active energy ray curability, an acrylate group or an acrylamide group is more preferred. From the viewpoint of forming intramolecular and intermolecular hydrogen bonds in addition to covalent bonds, an acrylamide group is particularly preferred. Furthermore, when D is used as a photopolymerization initiator, an N-monosubstituted acrylamide group is most preferred from the viewpoint of functioning as a hydrogen donor. When D is used as a photosensitizer, an acrylate group or an N,N-disubstituted acrylamide group is most preferred from the viewpoint of low viscosity of D and a curable composition containing D.

[0053] Compounds used in the reaction with the hydroxyl group-containing benzoylformamide derivative (D) include isocyanate compounds (b1), hydroxyl group-containing compounds (b2), ethylenically unsaturated group-reactive compounds (b3), and cyclic ether group-reactive compounds (b4). The reactive groups of b3 and b4 include hydroxyl groups, acid halides, halogens, isocyanate groups, acid anhydride groups, and epoxy groups. b1 includes general-purpose polyisocyanates, polyisocyanates with a polyol skeleton, and polyisocyanates with an isocyanurate ring.

[0054] The isocyanate compound (b1) is a compound having two or more isocyanate groups in the molecule. Specific examples include aliphatic polyisocyanates such as trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 1,2-propylene diisocyanate, 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and 2,2,4-trimethylhexamethylene diisocyanate; 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate; and 4,4'-diphenylmethane diisocyanate. Examples of the b1 include aromatic polyisocyanates such as cyclopentylene diisocyanate, cyclohexylene diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-hydrogenated xylylene diisocyanate, 1,4-hydrogenated xylylene diisocyanate, 2,5-norbornane diisocyanate, and 2,6-norbornane diisocyanate, as well as multimers such as adducts, isocyanurates, and biuret forms of these polyisocyanates. These b1s may be used alone or in combination of two or more.

[0055] The compound (b2) having a hydroxyl group is an alcohol or a polyol. Examples of the alcohol include monoalcohols using a linear alkyl group having 1 to 18 carbon atoms, such as methanol, ethanol, isopropanol, octanol, and isostearyl alcohol, and branched or cyclic alkyl groups having 3 to 18 carbon atoms; linear alkylene glycols having 2 to 18 carbon atoms, branched alkylene glycols having 3 to 18 carbon atoms, and cyclic alkylene glycols having 3 to 18 carbon atoms, such as ethylene glycol and 1,2-propylene glycol; and polyhydric alcohols such as glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol.

[0056] Examples of the polyols b2 include polyether polyols, polyester polyols, polycarbonate polyols, carbinol-modified silicones, and polyolefin polyols. Examples of the polyether polyols include linear polyalkylene glycols having 2 to 18 carbon atoms, branched polyalkylene glycols having 3 to 18 carbon atoms, and cyclic polyalkylene glycols having 3 to 18 carbon atoms, and examples of the polyolefin polyols include hydrogenated polyalkadiene polyols and polyalkadiene polyols. These b2s may be used singly or in combination of two or more types.

[0057] When the reactive group of the compound (b3) having an ethylenically unsaturated group and a reactive group is an acid anhydride group or an acid chloride group, examples of b3 include (meth)acrylic acid chloride, (meth)acrylic acid anhydride, maleic anhydride, and itaconic acid anhydride. When the reactive group is an epoxy group, examples of b3 include (meth)acrylic acid glycidyl ether and 4-hydroxybutyl (meth)acrylate glycidyl ether. When the reactive group is an isocyanate group, examples of b3 include 2-(meth)acryloyloxyethyl isocyanate. When the reactive group is a hydroxyl group, b3 is selected from the group consisting of hydroxyalkyl (meth)acrylate, N-hydroxyalkyl (meth)acrylamide, N-alkyl-N-hydroxyalkyl (meth)acrylamide, hydroxyalkyl (meth)vinyl ether, hydroxyalkyl (meth)allyl ether, hydroxyalkylmaleimide, hydroxyalkylstyrene, polyalkylene glycol mono(meth)acrylate, N-polyalkylene glycol mono(meth)acrylamide, N-alkyl-N-polyalkylene glycol mono(meth)acrylamide, N,N-bis(polyalkylene glycol) (meth)acrylamide, polyalkylene glycol mono(meth)vinyl ether, polyalkylene Examples of the copolymer include glycol mono(meth)allyl ether, polyalkylene glycol monomaleimide, hydroxyphenyl(meth)acrylate, hydroxyphenyl(meth)acrylamide, alkenyl alcohol, glycerin mono(meth)acrylate, glycerin mono(meth)acrylamide, glycerin di(meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, glycerin mono(meth)acrylamide, trimethylolpropane di(meth)acrylamide, pentaerythritol tri(meth)acrylamide, and dipentaerythritol penta(meth)acrylamide.The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, the alkylene is an alkylene group having 1 to 9 carbon atoms, and the alkenyl is a linear alkenyl group having 2 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, or a cyclic alkenyl group having 3 to 18 carbon atoms. These b3s may be used singly or in combination of two or more types.

[0058] When the reactive group of the compound (b4) having a cyclic ether group and a reactive group is a halogen, b4 can be epichlorohydrin. When the reactive group is a hydroxyl group, b4 is not particularly limited as long as it is a compound having one or more cyclic ether groups and one or more hydroxyl groups. Examples of b4 include hydroxyalkyl glycidyl ethers and hydroxyalkyl epoxides having a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, and 7-oxabicyclo[4.1.0]heptane-3-methanol as a compound containing an alicyclic epoxy group and a hydroxyl group. These b4s can be used alone or in combination.

[0059] The method for introducing urethane groups (urethanization) is not particularly limited as long as it is a known method. The reaction temperature is preferably within the range of room temperature to 90°C. If necessary, a solvent (c), a urethanization catalyst, or other additives may be used. Alternatively, a polymerizable compound can be used as the solvent instead of c. Examples of the polymerizable compound solvent include N-(meth)acroylmorpholine, alkyl(meth)acrylate esters, alkenyl(meth)acrylate esters, aryl(meth)acrylate esters, alkylene di(meth)acrylate esters, dialkylene glycol di(meth)acrylate esters, trialkylene glycol di(meth)acrylate esters, polyalkylene glycol di(meth)acrylate esters, N-substituted (meth)acrylamides, and N,N-disubstituted (meth)acrylamides. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms; the alkenyl is a linear alkenyl group having 2 to 18 carbon atoms or a cyclic alkenyl group having 3 to 18 carbon atoms; and the aryl is an aryl group having 6 to 8 carbon atoms. The urethanization reaction is preferably carried out in a light-blocking environment. Specifically, the reaction may be carried out in a light-blocking environment, in an ultraviolet-blocking environment such as a yellow room, under fluorescent lights that do not irradiate ultraviolet rays, or under a red darkroom safelight.

[0060] After the urethanization reaction, a crude product D containing the solvent (c) or the polymerizable compound used in place of c is obtained, and the crude product can be used as is in the curable composition, or can be used in the curable composition after removing c or the polymerizable compound. Methods for removing c include distillation under normal or reduced pressure, bubbling with dry air or an inert gas such as nitrogen, and freeze-drying.

[0061] Examples of reaction catalysts used in the urethanization reaction include quaternary ammonium salts, tertiary phosphine derivatives, tertiary amine derivatives, and organometallic compounds. Examples of quaternary ammonium salts include tetrabutylammonium bromide, triethylbenzylammonium chloride, tetrabutylphosphonium bromide, and tetraphenylphosphonium bromide. Examples of tertiary phosphines include triarylphosphines such as triphenylphosphine, tribenzylphosphine, and tritolylphosphine; tricycloalkylphosphines such as tricyclohexylphosphine; and trialkylphosphines such as triethylphosphine, tripropylphosphine, tributylphosphine, and trioctylphosphine. Examples of tertiary amines include trialkylamines such as triethylamine and tributylamine; dialkylarylamines such as dimethylbenzylamine and diethylbenzylamine; and triethanolamine. Examples of organometallic compounds include metal salts of metals such as zinc, tin, lead, zirconium, bismuth, cobalt, manganese, and iron with organic acids such as octenoic acid and naphthenic acid; dibutyltin dilaurate, dioctyltin dilaurate, tin 2-ethylhexanoate, dibutyltin diacetylacetonate, zirconium tetraacetylacetonate, titanium acetylacetonate, metal chelate compounds of aluminum acetylacetonate, cobalt acetylacetonate, iron acetylacetonate, copper acetylacetonate, and zinc acetylacetonate; potassium or sodium salts of alkylphosphonic acid; and sodium or potassium salts of fatty acids having 8 to 20 carbon atoms. These compounds may be used alone or in combination. Among these, quaternary ammonium salts, tertiary phosphine derivatives, and tin-, bismuth-, zirconium-, and iron-based organometallic compounds, which have high catalytic effects, are more preferred.

[0062] The amount of the urethanization reaction catalyst used is preferably 0.001 to 10% by mass relative to the total mass of the raw materials. If it is 0.001% by mass or more, the reaction can proceed quickly. If it is 10% by mass or less, coloration caused by the catalyst is low. Furthermore, it is more preferably 0.01 to 1.00% by mass.

[0063] The benzoyl formic acid amide derivative (D) of the present disclosure generates radicals, which are active growing species, upon irradiation with active energy rays. Examples of active energy rays include light energy rays such as visible light, electron beams, ultraviolet rays, infrared rays, X-rays, α-rays, β-rays, and γ-rays. Among these, ultraviolet rays are preferred in terms of the balance between the active energy ray generator, photopolymerization initiation rate, and safety. Examples of ultraviolet light sources include xenon lamps, low-pressure mercury lamps, high-pressure mercury lamps, metal halide lamps, UV-LED lamps, and microwave excimer lamps. UV-LED lamps capable of emitting high-output, safe ultraviolet rays in the 360-420 nm wavelength range are preferred. LED lamps capable of emitting rays of 365 nm, 385 nm, 395 nm, and 405 nm are also preferred.

[0064] The irradiation energy required for generating radicals from the benzoylformamide derivative (D) of the present disclosure can be expressed as an integrated light dose. The integrated light dose is 5 to 50,000 mJ / cm. 2 It is preferable that the range is 10 to 20,000 mJ / cm 2 If the irradiation energy is within this range, a sufficient number of growing active species can be generated from the photopolymerization initiator.

[0065] The benzoylformamide derivative (D) of the present disclosure can be incorporated into an active energy ray-curable composition as a photopolymerization initiator and used for various applications. The content of D in the curable composition varies depending on the structure of D and the composition of the curable composition, but is preferably 0.1% by mass or more. When D is incorporated at 0.1% by mass or more, photopolymerization can be initiated immediately upon irradiation with active energy rays, and the curable composition can be sufficiently cured. When D does not contain an ethylenically unsaturated group, the content of D in the curable composition is preferably 50% by mass or less, depending on the structure and molecular weight of D. Furthermore, from the viewpoint of easily adjusting the balance between the curability (curing rate) of the curable composition and the physical properties of the resulting cured product, the content of D is more preferably 0.5 to 20% by mass, and particularly preferably 1 to 10% by mass, relative to the total curable composition. When D contains an ethylenically unsaturated group, D alone can form a cured product, so D can be incorporated at 100% by mass. Furthermore, from the viewpoint of sufficiently curing the curable composition and obtaining good physical properties of the cured product, D can be used in combination with other polymerizable compounds (h), such as a compound having one ethylenically unsaturated group in the molecule (hereinafter referred to as a monofunctional unsaturated compound (h1)) and / or a compound having two or more ethylenically unsaturated groups in the molecule (hereinafter referred to as a polyfunctional unsaturated compound (h2)). In this case, the content of D in the entire curable composition is more preferably 0.5 to 90 mass%, particularly preferably 1 to 70 mass%.

[0066] The benzoylformamide derivative (D) of the present disclosure can be contained in an active energy ray-curable composition as a photosensitizer. The content of D in the curable composition varies depending on the structure of D and the composition of the curable composition, but is preferably 0.1% by mass or more. When D is contained in an amount of 0.1% by mass or more, D is excited by irradiation with active energy rays, activating the photopolymerization initiator in the curable composition, allowing photopolymerization to immediately begin and sufficient curing of the curable composition. D exhibits photosensitivity to both photoradical polymerization initiators and photoionic polymerization initiators (photocationic or photoanionic polymerization), and therefore can be used in combination with these photopolymerization initiators. When D does not contain an ethylenically unsaturated group or a cyclic ether group, the content of D in the curable composition is preferably 30% by mass or less, depending on the structure and molecular weight of D. Furthermore, from the viewpoint of easily adjusting the balance between the curability of the curable composition and the physical properties of the resulting cured product, the content of D is more preferably 0.5 to 20% by mass, and particularly preferably 1 to 10% by mass, relative to the total curable composition. When D contains an ethylenically unsaturated group and / or a cyclic ether group, D alone can form a cured product, and therefore D can be contained in an amount of 100% by mass. Furthermore, from the viewpoint of sufficiently curing the curable composition and ensuring good physical properties of the resulting cured product, D can be used in combination with a compound having a cyclic ether group in the molecule (hereinafter referred to as a cyclic ether-containing compound (h3)) as another polymerizable compound (h). In this case, the content of D is more preferably 0.5 to 90% by mass, and particularly preferably 1 to 70% by mass, of the entire curable composition.

[0067] The benzoylformamide derivative (D) of the present disclosure can be used either alone as a photopolymerization initiator or as a photosensitizer, or Ds with different structures can be appropriately combined as a photopolymerization initiator or a photosensitizer. When D is used as a photopolymerization initiator and a photosensitizer, the total content of D in the curable composition is 0.5 to 80 mass%, preferably 1 to 75 mass%, more preferably 2 to 50 mass%, and particularly preferably 3 to 30 mass%.

[0068] The polymerizable compound (h) includes a monofunctional unsaturated compound (h1) other than D, a polyfunctional unsaturated compound (h2), and a cyclic ether-containing compound (h3). The content of h is 0 to 99.9 mass% based on the total mass of the curable composition. From the viewpoint of suitably adjusting the physical properties of the cured product, the content of h is preferably 10 to 99.5 mass%, more preferably 30 to 99 mass%.

[0069] Examples of the monofunctional unsaturated compound (h1) include compounds containing a (meth)acrylate group, a (meth)acrylamide group, a vinyl group, an allyl group, a styryl group, and an acetylene group. These groups may be used alone or in combination of two or more. The content of h1 is preferably 0 to 90 mass %, more preferably 5 to 70 mass %, and particularly preferably 10 to 50 mass %, based on the total mass of the curable composition. h1 usually has a low viscosity, and its inclusion can be expected to reduce the viscosity of the curable composition and improve handleability.

[0070] The monofunctional unsaturated compound (h1) containing a (meth)acrylate group includes alkyl (meth)acrylates, hydroxyalkyl (meth)acrylates, (meth)acrylic acid alkyl carboxylic acids, (meth)acrylic acid alkyl sulfonic acids, (meth)acrylic acid alkyl phosphates, alkyloxy (hereinafter also referred to as alkoxy) alkylene glycol (meth)acrylates, alkoxy dialkylene glycol (meth)acrylates, alkoxy trialkylene glycol (meth)acrylates, alkoxy polyalkylene glycol (meth)acrylates, phenoxy alkylene glycol (meth)acrylates, phenoxy dialkylene glycol (meth)acrylates, phenoxy trialkylene glycol (meth)acrylates, phenoxy polyalkylene Examples of the acrylate include (meth)acrylates having a cyclic structure introduced therein, such as glycol (meth)acrylate, N-alkylamino (meth)acrylates, N-alkylaminoalkyl (meth)acrylates, N,N-dialkylaminoalkyl (meth)acrylates, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, bornyl (meth)acrylate, isobornyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-methyl-2-adamantyl (meth)acrylate, and N-(meth)acryloyloxyethyl norbornenecarboxamide. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, and the alkylene is an alkylene group having 1 to 4 carbon atoms.

[0071] Examples of the monofunctional unsaturated compound (h1) containing a (meth)acrylamide group include (meth)acrylamide, mono- or di-substituted (meth)acrylamide, N-(meth)acroylmorpholine, and diacetone (meth)acrylamide. Furthermore, examples of the mono- or di-substituted (meth)acrylamide include N-alkyl(meth)acrylamide, N,N-dialkyl(meth)acrylamide, N-hydroxyalkyl(meth)acrylamide, N,N-di(hydroxyalkyl)(meth)acrylamide, N-hydroxyalkyl-N-(4-hydroxyphenyl)(meth)acrylamide, N-alkyl-N-hydroxyalkyl(meth)acrylamide, N-alkyl-N-(4-hydroxyphenyl)(meth)acrylamide, 4-hydroxyphenyl(meth)acrylamide, N,N-di(4-hydroxyphenyl)(meth)acrylamide, N-alkoxyalkyl(meth)acrylamide, N,N-di(alkoxyalkyl)(meth)acrylamide, N-alkyl-N-alkoxyalkyl(meth)acrylamide, N-sulfoalkylacrylamide, N-alkylamino(meth)acrylamide, N-alkylaminoalkyl(meth)acrylamide, and N,N-dialkylaminoalkyl(meth)acrylamide. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms.

[0072] Examples of the vinyl group-containing monofunctional unsaturated compound (h1) include vinyl carboxylates having a carboxyl group of 1 to 18 carbon atoms, alkyl vinyl ethers, vinyl chloride, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinyloxazoline, maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, maleic monoalkyl esters, maleic dialkyl esters, maleic monoalkylamides, maleic dialkylamides, maleic alkylimides, fumaric monoalkyl esters, fumaric dialkyl esters, fumaric monoalkylamides, fumaric dialkylamides, itaconic monoalkyl esters, itaconic dialkyl esters, itaconic monoalkylamides, itaconic dialkylamides, itaconic alkylimides, vinyl carboxylic acids, vinyl sulfonic acids, and vinyl phosphoric acids. The alkyl groups are linear alkyl groups having 1 to 18 carbon atoms, branched alkyl groups having 3 to 18 carbon atoms, and cyclic alkyl groups having 3 to 18 carbon atoms.

[0073] Examples of the monofunctional unsaturated compound (h1) containing an allyl group include carboxylic acid allyl esters having a carboxyl group having 1 to 18 carbon atoms, alkyl allyl ethers, phenyl allyl ethers, alkylphenyl allyl ethers, allylamines, and mono- or dialkyl allylamines. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms.

[0074] Examples of the monofunctional unsaturated compound (h1) containing a styryl group include styrene, α-alkylstyrene, α-methylstyrene dimer, o-alkylstyrene, m-alkylstyrene, p-alkylstyrene, p-styrenesulfonic acid, etc. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms.

[0075] Examples of the polyfunctional unsaturated compound (h2) include compounds containing two or more unsaturated groups such as (meth)acrylate groups, (meth)acrylamide groups, vinyl groups, allyl groups, styryl groups, and acetylene groups. The compound may contain one type of unsaturated group alone, or two or more types in combination. To obtain good curability, it is more preferable that the unsaturated group contains one or more (meth)acrylate groups or (meth)acrylamide groups. The content of h2 is preferably 0 to 99% by mass, more preferably 1 to 70% by mass, and particularly preferably 5 to 50% by mass, based on the total mass of the curable composition. By including h2, the cured product obtained can be expected to have high strength and hardness, and excellent durability.

[0076] The polyfunctional unsaturated compound (h2) is, for example, allyl (meth)acrylate, allyloxyalkoxy (meth)acrylate, allyl (meth)acrylamide, allyloxyalkoxy (meth)acrylamide, vinyloxyalkoxy (meth)acrylate, diallylamine, alkyl diallylamine, dialkyl diallyl ammonium quaternary salt, alkylene glycol di(meth)acrylates, polyalkylene glycol di(meth)acrylates, bisphenol A diglycidyl ether (meth)acrylic acid adducts, alkoxylated bisphenol A di(meth)acrylates, polyester di(meth)acrylates, polycarbonate di(meth)acrylates, polyurethane di(meth)acrylates, polyurethane di(meth)acrylamides, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, ) acrylate, dipentaerythritol tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tri(meth)acryloyloxyethoxytrimethylolpropane, glycerin polyglycidyl ether poly(meth)acrylate, ethylene oxide-modified isocyanuric acid tri(meth)acrylate, ethylene oxide-modified dipentaerythritol penta(meth)acrylate, ethylene oxide-modified dipentaerythritol hexa(meth)acrylate, ethylene oxide-modified pentaerythritol tri(meth)acrylate, ethylene oxide-modified pentaerythritol tetra(meth)acrylate, succinic acid-modified pentaerythritol tri(meth)acrylate, and the like. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, and the alkylene is an alkylene group having 1 to 4 carbon atoms.

[0077] The number average molecular weight of the polyfunctional unsaturated compound (h2) is preferably 100 to 50,000. When the molecular weight is 100 or more, the resulting cured product has low cure shrinkage, which is preferred. When the molecular weight is 50,000 or less, the viscosity of the curable composition is low, which is preferred because it has excellent handleability. From these perspectives, the molecular weight of h2 is more preferably 200 to 20,000, and particularly preferably 300 to 15,000.

[0078] The cyclic ether-containing compound (h3) is a compound having one or more cyclic ether groups in the molecule, and the cyclic ether groups of h3 include epoxy groups, glycidyl groups, and oxetane groups. When multiple cyclic ether groups are contained, only one type may be contained, or two or more types may be contained in combination. Examples of compounds containing one cyclic ether group in h3 include alkyl glycidyl ether, alkyl epoxide, aryl glycidyl ether, epoxy cycloalkane, alkyl oxetane, glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, and vinyl glycidyl ether. Examples of compounds containing multiple cyclic ether groups in h3 include alkylene glycol diglycidyl ether, aryl diglycidyl ether, trimethylolpropane triglycidyl ether, (3,4-epoxycyclohexylmethyl) 3,4-epoxycyclohexane carboxylate, and alkylene bisoxetane. The alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, the alkylene is a linear alkylene group having 1 to 18 carbon atoms, a branched alkylene group having 3 to 18 carbon atoms, or a cyclic alkylene group having 3 to 18 carbon atoms, and the aryl is an aryl group having 6 to 18 carbon atoms. These h3s may be used singly or in combination of multiple types.

[0079] The content of the cyclic ether-containing compound (h3) is preferably 0 to 99 mass % of the total curable composition, more preferably 5 to 90 mass %, and particularly preferably 10 to 50 mass %. h3 usually has a low viscosity, and by including it, the viscosity of the curable composition can be reduced and the handleability can be improved.

[0080] The benzoyl formic acid amide derivative (D) of the present disclosure has high photopolymerization initiation ability in photoradical polymerization and can be suitably used as a photopolymerization initiator in various applications. When even higher photopolymerization initiation ability is required, D can be used in combination with other photopolymerization initiators. The photopolymerization initiators that can be used in combination are not particularly limited, and examples thereof include benzoins such as benzoin and benzoin alkyl ethers, acetophenones such as 2-hydroxy-2-methyl-1-phenylpropan-1-one, acylphosphine oxides such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoyl formate esters such as methyl benzoylformate, aminoacetophenones such as 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one, and oxime esters such as 1-(9,9-dimethyl-9H-fluoren-2-yl)-1,2-propanedione 2-(O-acetoxime). The photopolymerization initiator in combination can be used in combination with D in any ratio as needed, and one type may be used alone or multiple types may be used in combination.

[0081] Benzoyl formic acid amide derivatives (D) can be used in hybrid polymerization systems of photoradical polymerization and thermal radical polymerization. Thermal polymerization initiators that can be used in combination with D are not particularly limited, and include, for example, ketone peroxides such as methyl ethyl ketone peroxide, peroxyketals such as 1,1-di(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(t-hexylperoxy)cyclohexane, and 1,1-di(t-butylperoxy)cyclohexane, hydroperoxides such as 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, and p-menthane hydroperoxide, dialkyl peroxides such as dicumyl peroxide and di-t-butyl peroxide, diacyl peroxides such as dilauroyl peroxide and dibenzoyl peroxide, and peroxydicarbonates such as di(4-t-butylcyclohexyl)peroxydicarbonate and di(2-ethylhexyl)peroxydicarbonate. peroxyesters such as t-butylperoxy-2-ethylhexanoate, t-hexylperoxyisopropyl monocarbonate, t-butylperoxybenzoate, and 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate; azo initiators such as bis(1-phenyl-1-methylethyl)peroxide, 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(isobutyrate)dimethyl, and 1,1'-azobis(cyclohexane-1-carbonitrile); and polymeric azo polymerization initiators such as a polydimethylsiloxane unit-containing polymeric azo polymerization initiator (VPS-1001N, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and a polyethylene glycol unit-containing polymeric azo polymerization initiator (VPE-0201, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). These thermal polymerization initiators can be used in combination with D in any ratio as needed, and one type may be used alone, or multiple types may be used.

[0082] The benzoylformamide derivative (D) has a sufficient photosensitizing effect on photoradical polymerization and can be suitably used as a photosensitizer for photoradical polymerization in various applications. If a further photosensitizing effect is desired, it can be used in combination with other photosensitizers. The photosensitizers that can be used in combination with D are not particularly limited, and examples thereof include benzophenones, unsaturated ketones such as anthracene derivatives, 1,2-diketone derivatives such as benzil and camphorquinone, benzoin derivatives, anthraquinone derivatives, thioxanthone derivatives, coumarin derivatives, thiols, and disulfides. These photosensitizers can be used in combination with D in any ratio as needed, and one type may be used alone, or multiple types may be used.

[0083] Benzoyl formic acid amide derivatives (D) can be used as photosensitizers for photoionic polymerization in a variety of applications. When D is used in photoionic polymerization, the photoionic polymerization initiator is not particularly limited, and examples include photoanionic polymerization initiators such as 2-(9-oxoxanthen-2-yl)propionic acid 1,5,7-triazabicyclo[4.4.0]dec-5-ene and 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidium n-butyltriphenylborate, as well as antimony-based and triarylsulfonium salt-based photocationic polymerization initiators. In photoanionic or photocationic polymerization systems, the polymerization initiators of each polymerization system may be used alone or in combination.

[0084] The benzoylformamide derivative (D) has a sufficient photosensitizing effect for photoionic polymerization and can be used alone as a photosensitizer for photoionic polymerization. If a further photosensitizing effect is desired, it can be used in combination with other photosensitizers for photoionic polymerization. There are no particular limitations on the photoionic polymerization initiators that can be used in combination with D, and any photosensitizer that can be used for photoradical polymerization can be suitably used as a photosensitizer for photoionic polymerization. Furthermore, other photosensitizers can be used in combination with D in any ratio as needed, and one type can be used alone, or multiple types can be used.

[0085] The curable composition may further contain an organic solvent and water depending on the intended use and purpose of the curable composition and the resulting cured product. In this case, the organic solvent and water may be removed in advance before the polymerization reaction (curing), or the polymerization reaction may be carried out while the composition contains the organic solvent and water, and the organic solvent and water may be removed after curing. The contents of the organic solvent and water are not particularly limited, but from the viewpoint of energy saving and high efficiency, they are preferably 80 mass % or less, and more preferably 50 mass % or less, of the entire curable composition.

[0086] Examples of organic solvents used in the curable composition include alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate, propyl acetate, butyl acetate, methyl lactate, and ethyl lactate; alkylene glycols such as ethylene glycol and propylene glycol; polyalkylene glycols such as polyethylene glycol and polypropylene glycol; glycol ethers such as ethoxydiethylene glycol and methoxypropylene glycol; glycol esters such as propylene glycol acetate; tetrahydrofuran, methyltetrahydrofuran, cyclopentyl methyl ether, and methyltetrahydrofuran. Examples of suitable organic solvents include ethers such as dropyrane and methyl tert-butyl ether toluene, aromatic hydrocarbons such as xylene, aliphatic hydrocarbons such as hexane and cyclohexane, amides such as N,N-dimethylformamide, dimethylacetamide, and N,N-dimethylpropionamide, amide ethers such as β-methoxy-N,N-dimethylpropionamide and 3-butoxy-N,N-dimethylpropionamide, pyrrolidones such as 2-pyrrolidone and N-methylpyrrolidone, piperidines such as N-methylpiperidine, halogenated hydrocarbons such as methylene chloride, chloroform, and dichloroethane, sulfoxides such as dimethyl sulfoxide, and imidazolidinones such as 1,3-dimethyl-2-imidazolidinone. These organic solvents may be used alone or in combination of two or more types.

[0087] The benzoyl formic acid amide derivative (D) of the present disclosure can be used in a variety of applications, including UV flexographic inks, UV offset inks, UV screen inks, UV inkjet inks, active energy ray-curable nail cosmetic compositions (gel nails), UV-curable pressure-sensitive adhesives, UV-curable adhesives, active energy ray-curable sealants used in sealing materials or sealants, active energy ray-curable coating agents used in paints or coating agents for automobiles, electrical appliances, furniture, etc., active energy ray-curable resin compositions for decorative sheets used in decorative sheets used for surface coatings of automobiles, electrical appliances, etc., coating agents having self-repairing properties, three-dimensional objects, nail decoration materials, automobile exterior protection, functional members such as decorative films, resin compositions for active energy ray-curable self-repairing materials used in devices, etc., transparent adhesives, etc. The active energy ray-curable elastomer compositions are suitable for use in elastomers used in adhesive sheets, cushioning materials, packing, vibration-proofing materials, sound-absorbing materials, printing plates, sealants, abrasives, etc.; active energy ray-curable ink compositions for three-dimensional modeling used as model or support materials for 3D printers; active energy ray-curable vehicle coating compositions such as automotive paints; active energy ray-curable compositions used in various coating fields such as ship bottom paints, anti-fog materials, and antifouling paints; active energy ray-curable compositions used in medical device surface coatings; active energy ray-curable dental material compositions; active energy ray-curable photosensitive compositions; active energy ray-curable hydrogel compositions; active energy ray-curable intraocular implant material compositions; etc. The resulting hydrogel compositions are also suitable for use in a wide variety of fields, including hygiene fields such as superabsorbent resins, disposable diapers, and soft contact lenses; medical fields such as artificial organs; civil engineering and construction fields such as soil conditioners; agricultural fields such as water-retaining materials; and shock-absorbing materials. [Example]

[0088] The present invention will be described in detail below with reference to examples, but these examples are merely illustrative for the purpose of suitably explaining the present invention and are not intended to limit the present invention in any way. In the following, "parts" and "%" are all by mass unless otherwise specified.

[0089] The analytical methods used in the examples and comparative examples of the present disclosure, the instruments used, and the analytical conditions will be described below. (1) Fourier transform infrared spectroscopy (FT-IR analysis) FT-IR analysis was carried out using the following equipment. Nicolet iS50 (Thermo Fisher Scientific) (2) Liquid chromatography-mass spectrometry (LC-MS analysis) The conditions for LC-MS analysis are as follows. Column: XBride C18, 4.6 mm-150 mm, 3.5 μm (Nihon Waters Co., Ltd.) Eluent conditions: water / methanol / 1% formic acid aqueous solution = 60 / 30 / 10 Measurement wavelength: 258nm Column oven: 40℃ (3) Nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis) 1 H-NMR analysis was carried out using a 400 MHz apparatus manufactured by JEOL Ltd., and the resonance frequency of the methyl group of tetramethylsilane was set to 0.0 ppm. (4) Gel permeation chromatography analysis (GPC analysis) The conditions for the GPC analysis are as follows: Equipment: Prominence-I LC-2030C (Shimadzu Corporation) Guard column: Shodex KF-G (Showa Denko K.K.) Column: Shodex KF-803 (Showa Denko K.K.) Column temperature: 40℃ Mobile phase: tetrahydrofuran (THF) Flow rate: 0.5 mL / min Standard sample: polystyrene (5) High-performance liquid chromatography analysis (HPLC analysis) The conditions for HPLC analysis are as follows. Equipment: Prominence-I LC-2030C (Shimadzu Corporation) Column: Mightysil RP-18GP, 4.6 mm-250 mm, 5 μm (Kanto Chemical Co., Ltd.) Eluent conditions: methanol / 10 mM phosphoric acid aqueous solution = 50 / 50 Measurement wavelength: 258nm Column oven: 40℃

[0090] The various raw materials and solvents used in the examples and comparative examples are shown below. (1) Benzoylformic acid compound (a1) a1-1: methyl benzoylformate a1-2: 3,4,5-trimethoxybenzoylformic acid methyl ester a1-3: 4-Methoxycarbonylbenzoylformic acid methyl ester a1-4: 4-acetoxybenzoylformic acid methyl ester a1-5: 4-dimethylaminobenzoylformic acid methyl ester a1-6: 4-methylbenzoylformic acid ethyl ester a1-7: 2-Acetaminobenzoylformic acid methyl ester a1-8: 4-Methoxybenzoylformic acid methyl ester a1-9: 3,5-dimethoxybenzoylformic acid methyl ester a1-10: 3-Methoxybenzoylformic acid methyl ester a1-11: 3-butoxybenzoylformic acid ethyl ester a1-12: 4-bromobenzoylformic acid methyl ester (2) Amino group-containing compound (a2) a2-1: (2S,3S,4R)-2-amino-1,3,4-octadecanetriol a2-2: Diethanolamine a2-3: 3-Piperidinemethanol a2-4: Dimethylamine (11% methanol solution, 2.0 mol / L) a2-5: 8-amino-1-octanol a2-6: Aminoethanol a2-7: 2-amino-2-methyl-1-propanol a2-8: 1,3-diamino-2-propanol a2-9: DL-2-amino-1-butanol a2-10: 4-aminobenzyl alcohol a2-11: 2-(2-aminoethoxy)ethanol a2-12: Trimethylolaminomethane a2-13: D-glucamine a2-14: 3-amino-1,2-propanediol a2-15: 2-amino-1,3-propanediol a2-16: 2-amino-2-ethyl-1,3-propanediol (3) Isocyanate compound (b1) b1-1: Isophorone diisocyanate b1-2: Trimethylhexamethylene diisocyanate b1-3: 1,3,5-tris[(5-isocyanato-1,3,3-trimethylcyclohexyl)methyl]-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (isocyanurate of isophorone diisocyanate) b1-4: 1,3,5-tris(6-isocyanatehex-1-yl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (isocyanurate of hexamethylene diisocyanate) b1-5: Hexamethylene diisocyanate b1-6: Methylene bisphenyl isocyanate b1-7: Pentamethylene diisocyanate (Stabio PDI, manufactured by Mitsui Chemicals, Inc.) b1-8: Dicyclohexylmethane-4,4-diisocyanate (4) Compounds having a hydroxyl group (b2) b2-1: Polyethylene glycol (number average molecular weight 300) b2-2: Hydrogenated poly-1,2-butadiene with hydroxyl groups at both ends (number average molecular weight 1,000) (GI-1000, manufactured by Nippon Soda Co., Ltd.) b2-3: ETERNACOLL UH-50 (number average molecular weight 500) (manufactured by Ube Industries, Ltd.) b2-4: Silicone modified with hydroxyl groups at both ends (number average molecular weight 1,700) (Shin-Etsu Silicone KF-6001, manufactured by Shin-Etsu Chemical Co., Ltd.) b2-5: 1,4-butanediol b2-6: Isopropanol b2-7: Isostearyl alcohol b2-8: Adeka Polyether BPX-2000 (manufactured by ADEKA Corporation) b2-9: Kuraray Polyol P-1010 (number average molecular weight 1,000) (Kuraray Co., Ltd.) b2-10: Uniol TG330 (polyoxypropylene glyceryl ether, molecular weight 330, manufactured by NOF Corporation) B2-11: Polypropylene glycol (number average molecular weight 1,000) b2-12: Kuraray Polyol P-6010 (number average molecular weight 6,000) (Kuraray Co., Ltd.) b2-13: Polytetramethylene glycol (number average molecular weight 650) (BioPTMG650, manufactured by Mitsubishi Chemical Corporation) (5) Compound (b3) having an ethylenically unsaturated group and a reactive group b3-1: 2-Acryloyloxyethyl isocyanate b3-2: N-(2-hydroxyethyl)acrylamide (registered trademark "Kohshylmer" and "HEAA" manufactured by KJ Chemicals Co., Ltd.) b3-3: acrylic acid chloride b3-4: Allyl chloride b3-5: acrylonitrile b3-6: Unsaturated polyester diol (polyester consisting of 1,5-methylpentanediol / maleic acid / adipic acid = 4 / 1 / 2 (molar ratio)) b3-7: 2-hydroxyethylmaleimide B3-8: Hydroxyethyl acrylate b3-9: N-(hydroxymethyl)acrylamide B3-10: 4-hydroxybutyl acrylate B3-11: Pentaerythritol triacrylate B3-12: Hydroxyethyl methacrylate b3-13: N-(2-hydroxyethyl) methacrylamide B3-14: 4-hydroxybutyl vinyl ether b3-15: oleyl alcohol B3-16: Polypropylene glycol (6) monoacrylate B3-17: Dipentaerythritol pentaacrylate (6) Compound (b4) having a cyclic ether group and a reactive group b4-1: epichlorohydrin b4-2: 7-oxabicyclo[4.1.0]heptane-3-methanol b4-3: 2-hydroxyethyl glycidyl ester (7) Solvent (c) c-1: Toluene c-2: 1,2-dichloroethane c-3: Ethyl acetate c-4: 4-Methyltetrahydrofuran c-5: 3-Methoxy-N,N-dimethylpropionamide (registered trademark "Kohshylvent" or "KJCMPA" manufactured by KJ Chemicals Co., Ltd.)

[0091] The monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), cyclic ether-containing compound (h3), photopolymerization initiator (E), photosensitizer (I), thermal polymerization initiator (J), and other additives (k) used in the active energy ray-curable compositions of the Examples and Comparative Examples are shown below. (8) Polymerizable compound (h) (8-1) Monofunctional unsaturated compound (h1) h1-1: N-Acroylmorpholine (registered trademark "Kohshylmer" and "ACMO", manufactured by KJ Chemicals Co., Ltd.) h1-2: Isobornyl acrylate h1-3: N,N-diethylacrylamide (registered trademark "Kohshylmer" and "DEAA", manufactured by KJ Chemicals Co., Ltd.) h1-4: 4-hydroxybutyl acrylate h1-5: 3-Acryloylaminopropionic acid methyl ester h1-6: N-acryloyloxyethyl norbornenecarboxamide (registered trademark "Kohshylmer", manufactured by KJ Chemicals Co., Ltd.) h1-7: N-octylacrylamide (registered trademark "Kohshylmer", manufactured by KJ Chemicals Co., Ltd.) h1-8: N-(2-hydroxyethyl)acrylamide (registered trademark "Kohshylmer" and "HEAA" manufactured by KJ Chemicals Co., Ltd.) h1-9: t-Butylcyclohexyl acrylate (registered trademark "Kohshylmer", manufactured by KJ Chemicals Co., Ltd.) h1-10: tetrahydrofurfuryl acrylate h1-11: N-vinylpyrrolidone h1-12: N-oleyl acrylamide (registered trademark "Kohshylmer", manufactured by KJ Chemicals Co., Ltd.) h1-13: Diacetone acrylamide (registered trademark "Kohshylmer", manufactured by KJ Chemicals Co., Ltd.) h1-14: N,N-dimethylacrylamide (registered trademark "Kohshylmer" or "DMAA", manufactured by KJ Chemicals Co., Ltd.) H1-15: Hydroxyethyl methacrylate h1-16: Phenoxyethyl acrylate h1-17: Lauryl acrylate h1-18: Isobornyl methacrylate h1-19: 2-Methacryloyloxyethyl acid phosphate (8-2) Polyfunctional unsaturated compound (h2) h2-1: hexanediol diacrylate h2-2: Dipentaerythritol hexaacrylate h2-3: Quick Cure 8100 (registered trademark "Quick Cure", manufactured by KJ Chemicals Co., Ltd.) h2-4: Quick Cure 7100 (registered trademark "Quick Cure", manufactured by KJ Chemicals Co., Ltd.) h2-5: Polyethylene glycol (14) diacrylate h2-6: Urethane diacrylate (UV3000, manufactured by Mitsubishi Chemical Corporation) h2-7: Trimethylolpropane triacrylate h2-8: Pentaerythritol triacrylate h2-9: Quick Cure 7300 (registered trademark "Quick Cure", manufactured by KJ Chemicals Co., Ltd.) h2-10: Dimethylol-tricyclodecane diacrylate h2-11: Urethane diacrylate (UV6630, manufactured by Mitsubishi Chemical Corporation) h2-12: Polyethylene glycol (20)-incorporated bisphenol A diacrylate h2-13: 2-(2-vinyloxyethoxy)ethyl acrylate H2-14: Diethylene glycol divinyl ether h2-15: Bisphenol A epoxy acrylate oligomer (Miramer PE-210, manufactured by MIWON) h2-16: Polyethylene glycol (10)-incorporated bisphenol A diacrylate H2-17: 2,4-dimethyl-1,6-hexanediylbis[carbamate 2-(methacryloyloxy)ethyl] h2-18: Ethylenebisacrylamide h2-19: Triethylene glycol dimethacrylate (9) Cyclic ether-containing compound (h3) h3-1: 2-ethylhexyl glycidyl ether h3-2: Bisphenol A diglycidyl ether h3-3: 1,6-hexanediol diglycidyl ether h3-4: Trimethylolpropane triglycidyl ether h3-5: butyl glycidyl ether h3-6: 4-hydroxybutyl acrylate glycidyl ether (10) Photopolymerization initiator (E) E-1: Oligomer of 2-hydroxy-1-(4-isopropenylphenyl)-2-methylpropan-1-one (ESACURE KIP 150, manufactured by IGM Resin BV) E-2: Methyl benzoylformate (Omnirad MBF, manufactured by IGM Resin BV) E-3: 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Omnirad TPO, manufactured by IGM Resin BV) E-4: Kohshylex-I 3003 (registered trademark "Kohshylex", manufactured by KJ Chemicals Co., Ltd.) E-5: 1-hydroxycyclohexyl phenyl ketone (Omnirad 184, manufactured by IGM Resin BV) E-6: 2-hydroxy-2-methylpropiophenone (Omnirad 1173, manufactured by IGM Resin BV) E-7: 1-[4-(2-hydroxyethyl)-phenyl]-2-hydroxy-methylpropanone (Omnirad 2959, manufactured by IGM Resin BV) E-8: Benzophenone E-9: α-[(4-benzoylphenoxy)acetyl]-ω-{[(4-benzoylphenoxy)acetyl]oxy}poly(oxybutane-1,4-diyl) (Omnipol BP, manufactured by IGM Resin BV) E-10: 2-(9-oxoxanthen-2-yl)propionic acid 1,5,7-triazabicyclo[4.4.0]dec-5-ene E-11: 1,2-Dicyclohexyl-4,4,5,5-tetramethylbiguanidium n-butyltriphenylborate (11) Photosensitizers (I) I-1: Poly(ethylene glycol) bis(p-dimethylaminobenzoate) (Omnipol ASA, manufactured by IGM Resin BV) I-2: Bis N,N-[2-(4-dimethylaminobenzoyl)oxyethylene-1-yl]methylamine (Esacure A 198, manufactured by IGM Resin BV) I-3: Isopropylthioxanthone I-4: 2-Ethylanthraquinone I-5: Polytetramethylene glycol (3) carboxymethoxioxanthone diester (Omnipol TX, manufactured by IGM Resin BV) (12) Thermal polymerization initiator (J) J-1: Azobisisobutyronitrile (13) Other additives (k) k-1: Pentaerythritol tetrakis(3-mercaptobutyrate) k-2: Methyl-5-norbornene-2,3-dicarboxylic anhydride k-3: BYK JET9151 (pigment dispersant, maleimide-styrene copolymer with ammonium salt structure, manufactured by BYK Chemie) k-4: Carbon black dispersion (Mitsubishi Chemical Corporation) k-5: Pigment Yellow 155 k-6:VALIFAST BLUE1613 (manufactured by ORIENT CHEMICAL INDUSTRIES Co., LTD.) k-7: BYK-331 (leveling agent, polyether-modified polydimethylsiloxane, manufactured by BYK Chemie) k-8: Petrotack 100V (manufactured by Tosoh Corporation) k-9: Trimethylsilyl group surface-modified silica (AEROSIL RX200, manufactured by Nippon Aerosil Co., Ltd.) k-10: Hydrogenated rosin (non-polymerizable polymer, Tackyfire KE-359, manufactured by Arakawa Chemical Industries) k-11: Reoloseal QS-30 (Tokuyama Corporation) K-12: Inorganic filler (titanium oxide) K-13: Methacrylic acid / methyl methacrylate / styrene copolymer binder K-14: Polyvinyl alcohol JC-25 (manufactured by Nippon Vaccination & Poval Co., Ltd.) k-15: Eleminol JS-20 (manufactured by Sanyo Chemical Industries, Ltd.)

[0092] Example 1 Synthesis of benzoylformamide derivative (D-1) A 1,000 mL flask equipped with a reflux condenser, stirrer, thermometer, and dropping funnel was charged with 197.0 g (1.20 mol) of methyl benzoylformate (a1-1), 317.5 g (1.00 mol) of (2S,3S,4R)-2-amino-1,3,4-octadecanetriol (a2-1), 500 g of toluene (c-1) as a solvent, and 1.0 g (0.01 mol) of triethylamine (TEA) as a catalyst, and the mixture was heated to 70 °C with stirring. After reacting at 70 °C for 8 hours, the unreacted raw materials, solvent, by-product methanol, and catalyst were distilled off under reduced pressure to obtain a pale yellow solid, benzoylformamide derivative (D-1) (yield 85%). D-1 was identified as follows: 1 H-NMR analysis was performed, and the chemical shift values ​​of representative protons are shown in Table 1-1. Liquid chromatography mass spectrometry (LC-MS analysis) revealed that the molecular weight of the product was 450 (the molecular ion peak in the mass spectrum was 451). 1 The results of H-NMR and LC-MS analysis confirmed that the product was the benzoylformamide derivative (D-1) shown in Table 1-1.

[0093] Examples 2, 3, 5 to 20 Synthesis of benzoylformamide derivatives (D-2), (D-3), (D-5) to (D-20) The reaction was carried out under the same conditions as in Example 1 using the raw materials and their ratios shown in Tables 1-1 and 1-2 to obtain benzoylformamide derivatives (D-2), (D-3), (D-5) to (D-20). The resulting benzoylformamide (D) was identified in the same manner. 1 H-NMR analysis and LC-MS analysis were performed, and the chemical shift values ​​of representative protons, as well as the molecular weight and yield of the product are shown in Tables 1-1 and 1-2. 1 From the results of H-NMR and LC-MS analysis, the products were confirmed to be the benzoylformamide derivatives (D-2), (D-3), and (D-5) to (D-20) shown in Tables 1-1 and 1-2.

[0094] Example 4 Synthesis of benzoylformamide derivative (D-4) The catalyst TEA in Example 1 was changed to sodium methoxide, and methyl 4-acetoxybenzoylformate (a1-4) was reacted with dimethylamine and purified under the same conditions as in Example 1, to obtain a pale yellow solid, benzoylformamide derivative (D-4) (yield 75%). 1 D-4 was identified by H-NMR and LC-MS analysis, and the analytical data and the chemical formula of D-4 are shown in Table 1-1.

[0095] Example 21 Synthesis of benzoylformamide derivative (D-21) 243.1 g (1.00 mol) of methyl 4-bromobenzoylformate (a1-12), 143.0 g (1.20 mol) of 2-amino-2-ethyl-1,3-propanediol (a2-16), and 362 g of Adeka Polyether BPX-2000 (b2-8) instead of solvent (c) were added, and the reaction was carried out under the same conditions as in Example 1. Thereafter, nitrogen gas was introduced at 100 cm at 25°C. 3 The mixture was passed through (bubbling) at a flow rate of 1 / min for 10 minutes to remove unreacted raw materials and by-product methanol, and a solution of benzoyl formic acid amide derivative (D-21) b2-8 was obtained (yield 84%). 1 H-NMR analysis was performed, and the chemical shift values ​​of representative protons are shown in Table 1-2. LC-MS analysis confirmed the molecular weight of D-21, and the obtained solution was confirmed to be a mixture of D-21 and b2-8 in a mass ratio of 1 / 1.

[0096] Example 22 Synthesis of benzoylformamide derivative (D-22) A 300 mL flask equipped with a reflux condenser, stirrer, thermometer, and dropping funnel was charged with 45.7 g of the benzoylformamide derivative (D-2) synthesized in Example 2, 54.3 g of 2-acryloyloxyethyl isocyanate (b3-1), and 50 g of ethyl acetate (c-3). 0.02 g of bismuth tris(2-ethylhexanate) was added as a catalyst to the mixture, and the reaction was carried out at 70°C for 4 hours with stirring. FT-IR analysis confirmed the disappearance of the isocyanate groups, and the solvent was removed under reduced pressure to obtain a pale yellow viscous solid product (98% yield). FT-IR analysis of the product confirmed the presence of urethane groups and the benzoylformamide group (disubstituted) derived from D-2. 1 H-NMR analysis confirmed the presence of acrylate groups (5.85 ppm, 6.20 ppm, 6.45 ppm). LC-MS analysis further confirmed that the molecular weight of the product was 520, confirming that the product was the benzoylformamide derivative (D-22) shown in Table 2-1. Table 2-1 shows the chemical formula, molecular weight, and number of benzoylformamide groups per molecule of D-22, the number of atoms directly linked between the nitrogen atom of the benzoylformamide group and the nitrogen atom of the nearest urethane group, and the ratio of the number of urethane groups to the number of benzoylformamide groups per molecule.

[0097] Example 23 Synthesis of benzoylformamide derivative (D-23) The reaction of 50.0 g of benzoylformamide derivative (D-3), 32.9 g of isophorone diisocyanate (b1-1), and 17.1 g of N-(2-hydroxyethyl)acrylamide (b3-2) was carried out in the presence of 0.01 g of catalyst dibutyltin dilaurate in the same manner as in Example 22, except that no reaction solvent was used, to obtain a pale yellow viscous solid product (yield 96%). FT-IR analysis of the product confirmed the presence of urethane groups and benzoylformamide groups (disubstituted) derived from D-3. 1 H-NMR analysis confirmed the presence of acrylamide groups (5.60 ppm, 6.10 ppm, 6.50 ppm). LC-MS analysis further confirmed that the product had a molecular weight of 675, confirming that the product was the benzoylformamide derivative (D-23) shown in Table 2-1. The chemical formula and other data for D-23 are summarized in Table 2-1.

[0098] Example 24 Synthesis of benzoylformamide derivative (D-24) In a 300 mL flask equipped with a reflux condenser, a stirrer, a thermometer, and a dropping funnel, 74.7 g of the benzoylformamide derivative (D-5) synthesized in Example 5 and 100 g of 1,2-dichloroethane (c-2) were added and mixed. The mixture was cooled to -10°C, and while maintaining the temperature at -10 to 0°C, 25.3 g of acrylic acid chloride (b3-3) was added dropwise to cause a reaction. Extraction was then performed with an alkaline aqueous solution, and the solvent in the organic layer was removed under reduced pressure to obtain a pale yellow viscous liquid product (yield 84%). FT-IR analysis of the product confirmed the presence of the benzoylformamide group (mono-substituted) derived from D-5. 1 H-NMR analysis confirmed the presence of acrylate groups, and LC-MS analysis confirmed that the molecular weight of the product was 331. The chemical formula and other data of product D-24 are summarized in Table 2-1.

[0099] Example 25 Synthesis of benzoylformamide derivative (D-25) A 500 mL flask equipped with a reflux condenser, stirrer, thermometer, and dropping funnel was charged with 6.0 g of sodium hydride and 50 g of 4-methyltetrahydrofuran (c-4). 63.6 g of the benzoylformamide derivative (D-18) was dissolved in 50 g of c-4 and added to the dropping funnel. The resulting solution was added dropwise over 30 minutes while monitoring the amount of hydrogen gas generated. After the addition was complete, 36.4 g of allyl chloride (b3-4) was added and the reaction mixture was allowed to react at 25 °C for 24 hours. 100 mL of ion-exchanged water was then added to deactivate the remaining sodium hydride, and c-4 was isolated. The extract was then extracted three times with saturated saline. The extract was concentrated using an evaporator, purified by silica gel column chromatography, and the solvent was removed under reduced pressure to obtain a pale yellow viscous liquid (43% yield). FT-IR analysis of the product confirmed the presence of the mono-substituted benzoylformamide group derived from D-18. 1H-NMR analysis confirmed the presence of allyl ether groups (5.00 ppm, 5.05 ppm, 5.85 ppm, 3.85 ppm). LC-MS analysis confirmed that the molecular weight of the product was 347. The chemical formula and other data for D-25 are summarized in Table 2-1.

[0100] Example 26 Synthesis of benzoylformamide derivative (D-26) A 500 mL flask equipped with a reflux condenser, stirrer, thermometer, and dropping funnel was charged with 40.4 g of trifluoromethanesulfonic acid. While cooling, 4.8 g of ion-exchanged water was added and mixed to obtain trifluoromethanesulfonic acid hydrate. A solution of 86.6 g of benzoylformamide derivative (D-9), 13.4 g of acrylonitrile (b3-5), and 100 g of 4-methyltetrahydrofuran (c-4) was added dropwise to the flask at 40 °C over 2 hours. After the reaction was completed, the mixture was extracted twice with ion-exchanged water, and the organic layer was concentrated and purified by silica gel column chromatography. The solvent was then removed under reduced pressure to obtain a pale yellow viscous liquid (38% yield). FT-IR analysis of the product confirmed the presence of the benzoylformamide group (mono-substituted) derived from D-9. 1 H-NMR analysis confirmed the presence of an acrylamide group and two benzoylformamide groups. LC-MS analysis further confirmed that the molecular weight of the product was 407. The chemical formula and other data for D-26 are summarized in Table 2-1.

[0101] Examples 27, 28, 30, 32, 36 to 39 Synthesis of benzoylformamide derivatives (D-27), (D-28), (D-30), (D-32), (D-36) to (D-39) The benzoylformamide derivative (D) was synthesized in the same manner as in Example 22 using the raw materials shown in Tables 2-1 to 2-3. 1 The product was identified by H-NMR analysis and LC-MS analysis, and the chemical formula and other data of the product are summarized in Tables 2-1 to 2-3. 1H-NMR analysis confirmed the presence of maleimide groups (7.05 ppm), acrylate groups (5.85 ppm, 6.20 ppm, 6.45 ppm), and acrylamide groups (5.60 ppm, 6.10 ppm, 6.50 ppm).

[0102] Example 29 Synthesis of benzoylformamide derivative (D-29) Using the same reaction apparatus as in Example 23, 18.8 g of benzoyl formic acid amide derivative (D-7), 23.5 g of trimethylhexamethylene diisocyanate (b1-2), 57.7 g of unsaturated polyester diol (b3-6), and 0.05 g of zirconium tetrakisacetylacetonate as a catalyst were mixed and reacted for 5 hours with stirring at 60°C. FT-IR analysis of the reaction solution confirmed the disappearance of the isocyanate groups, and a pale yellow viscous liquid product was obtained (yield 96%). FT-IR analysis of the product confirmed the presence of urethane groups and benzoyl formic acid amide groups. 1 H-NMR analysis confirmed the presence of maleic ester groups (6.30 ppm). GPC analysis calculated the number average molecular weight (Mn) to be 2,700. The chemical formula and other data of the benzoyl formic acid amide derivative (D-29) confirmed from these results are shown in Table 2-1.

[0103] Examples 31, 34, 35, 40 to 46, 48 to 54 Synthesis of benzoylformamide derivatives (D-31), (D-34), (D-35), (D-40) to (D-46), (D-48) to (D-54) Using the raw materials shown in Tables 2-2 to 2-6, benzoylformamide derivatives (D) were synthesized in the same manner as in Example 23. FT-IR analysis confirmed the presence of urethane groups and benzoylformamide groups. 1H-NMR analysis confirmed the presence of acrylate groups (5.85 ppm, 6.20 ppm, 6.45 ppm), methacrylate groups (5.65 ppm, 6.20 ppm), acrylamide groups (5.60 ppm, 6.10 ppm, 6.50 ppm), methacrylamide groups (5.60 ppm, 6.20 ppm), vinyl ether groups (4.75 ppm, 4.80 ppm, 6.75 ppm), and various unsaturated groups. Furthermore, GPC analysis was used to calculate the number-average molecular weight (Mn) of the product. The chemical formulas and other data for the benzoylformamide derivatives (D-31), (D-34), (D-35), (D-40) to (D-46), and (D-48) to (D-54) are summarized in Tables 2-2 to 2-6. Additionally, D-41 was synthesized from biomass diisocyanate (b1-7), so the biobased content was 27.0%. D-53 was synthesized from biomass polyol (b2-13), so the biobased content was 24.9%. The biobased content was calculated using the method described in ISO 16620-1.

[0104] Example 33 Synthesis of benzoylformamide derivative (D-33) Using the raw materials shown in Table 2-2, 39.6 g of benzoylformamide derivative (D-10), 39.8 g of isophorone diisocyanate (b1-1), 20.6 g of N-(hydroxymethyl)acrylamide (b3-9), 100.0 g of polymerizable compound N-acroylmorpholine (h1-1) (instead of solvent (c)), and 0.02 g of bismuth tris(2-ethylhexanoate) as a catalyst were mixed and reacted for 6 hours with stirring at 60 ° C. The disappearance of the isocyanate group was confirmed by FT-IR analysis of the reaction solution, and a pale yellow liquid product was obtained (yield 99%). The presence of urethane groups and benzoylformamide groups was confirmed by FT-IR analysis of the product, 1 H-NMR analysis confirmed the presence of acrylamide groups (5.60 ppm, 6.10 ppm, 6.50 ppm) derived from b3-9. LC-MS analysis also confirmed that the molecular weight of D-33, which had no methoxy groups after standing for 24 hours, was 588, confirming that a solution of D-33 in h1-1 (50% by mass) had been obtained. These analytical results are shown in Table 2-2.

[0105] Example 47 Synthesis of benzoylformamide derivative (D-47) Using a reaction apparatus similar to that used in Example 23, 19.8 g of a b2-8 solution of benzoyl formic acid amide derivative (D-21) (D-21 / b2-8 = 1 / 1, mass ratio), 15.7 g of trimethylhexamethylene diisocyanate (b1-2), 58.8 g of b2-8, 1.7 g of N-(hydroxyethyl)acrylamide (b3-2), 4.0 g of oleyl alcohol (b3-15), and 0.01 g of catalyst dibutyltin dilaurate were mixed and reacted for 6 hours with stirring at 60 °C. FT-IR analysis of the reaction solution confirmed the disappearance of the isocyanate groups, and a pale yellow liquid product was obtained (yield 95%). FT-IR analysis of the product confirmed the presence of urethane groups and benzoyl formic acid amide groups. 1 H-NMR analysis confirmed the presence of acrylamide groups (5.60 ppm, 6.10 ppm, 6.50 ppm) derived from b3-2 and unsaturated groups (5.35 ppm) derived from oleyl groups derived from b3-15. Furthermore, GPC analysis calculated the number average molecular weight (Mn) of D-47 to be 7,200. The chemical formula and other data of D-47 confirmed from these results are shown in Table 2-4.

[0106] Example 55 Synthesis of benzoylformamide derivative (D-55) A 300 mL flask equipped with a reflux condenser, stirrer, thermometer, and dropping funnel was charged with 67.6 g of benzoylformamide derivative (D-6) and 50.0 g of 4-methyltetrahydrofuran (c-4), mixed, and then 21.6 g of epichlorohydrin (b4-1) was added. While maintaining the temperature at 20°C, 0.5 g of boron trifluoride diethyl ether was added, and then 10.8 g of b4-1 was added dropwise over 1 hour. After the addition was completed, the reaction was continued for another 2 hours. The reaction solution was filtered, the filtrate was washed with ion-exchanged water, and the solvent was removed from the organic layer under reduced pressure to obtain a pale yellow liquid product (yield 65%). FT-IR analysis of the product confirmed the presence of benzoylformamide groups. 1H-NMR analysis confirmed the presence of glycidyl groups (3.00 ppm, 3.85 ppm). Furthermore, LC-MS analysis confirmed that the molecular weight of the product was 249. From these results, the product was identified as the benzoylformamide derivative (D-55) shown in Table 2-6.

[0107] Examples 56 to 58 Synthesis of benzoylformamide derivatives (D-56) to (D-58) Using the raw materials shown in Table 2-6, benzoylformamide derivative (D) was synthesized in the same manner as in Example 23. The presence of a urethane group and a benzoylformamide group was confirmed by FT-IR analysis. 1 The presence of cyclic ethers and unsaturated groups was confirmed by H-NMR analysis. 1 H-NMR analysis confirmed the presence of alicyclic epoxy groups (2.95 ppm, 3.05 ppm), glycidyl groups (3.00 ppm, 3.85 ppm), and acrylate groups (5.85 ppm, 6.20 ppm, 6.45 ppm). Furthermore, the molecular weight of the product in Example 56 was measured by LC-MS analysis, and the number average molecular weight (Mn) of the product in Examples 57 and 58 was calculated by GPC analysis, and is shown in Table 2-6. The chemical formulas and other data of the benzoylformamide derivatives (D-56) to (D-58) are summarized in Table 2-6.

[0108] [Table 1-1]

[0109] [Table 1-2]

[0110] [Table 2-1]

[0111] [Table 2-2]

[0112] [Table 2-3]

[0113] [Table 2-4]

[0114] [Table 2-5]

[0115] [Table 2-6]

[0116] Examples 59 to 100 and Comparative Examples 1 to 3 (Preparation and Evaluation of Active Energy Ray-Curable Compositions) Using the synthesized benzoylformamide derivatives (D-1) to (D-54) as examples and commercially available photopolymerization initiators (E-1) to (E-3) as comparative examples, the monofunctional unsaturated compound (h1), the polyfunctional unsaturated compound (h2), the photosensitizer (I), and other components (k) were weighed in the proportions shown in Tables 3-1 and 3-2 and mixed at 25°C for 30 minutes to obtain active energy ray-curable compositions (hereinafter referred to as "curable compositions"). The compatibility of the obtained curable compositions and their curability with light of different wavelengths were evaluated. Furthermore, photocured products of the curable compositions were prepared, and the content of low-molecular-weight components derived from the photopolymerization initiator in the cured products, as well as the photoyellowing resistance and durability of the cured products, were evaluated using the methods described below. The results are shown in Tables 3-1 and 3-2.

[0117] <compatibility> The state of the curable composition was visually observed, and the compatibility was evaluated into four stages. ++: High transparency, no turbidity or phase separation was observed. +: High transparency, but slight turbidity was observed. ±: No phase separation was observed, but turbidity was observed. -: Turbidity and phase separation were observed.

[0118] <Curability> The curable composition was applied to a polyethylene terephthalate film (Cosmoshine A-4100, corona-treated surface, thickness 100 μm, manufactured by Toyobo Co., Ltd.) (hereinafter referred to as PET film) using a bar coater to a film thickness of 20 μm. The coating film was cured by irradiating it with light of different wavelengths, and the cumulative amount of light required until the tackiness disappeared when touched was determined, and the curability was evaluated into four levels. Three types of ultraviolet irradiation lamps, 1) to 3) below, were used. The lower the cumulative amount of light required until the tackiness disappeared, the higher the curability. 1) High-pressure mercury lamp: wavelength 200-450nm, illuminance 100mW / cm 2 2) UV-LED lamp: wavelength 385nm, illuminance 100mW / cm 2 3) UV-LED lamp: wavelength 405 nm, illuminance 100 mW / cm 2 ++: Accumulated light intensity 500mJ / cm 2 The tack was gone in less than. +: Accumulated light intensity 500mJ / cm 2 More than 1,000mJ / cm 2 The tack was gone in less than. ±: Accumulated light intensity 1,000mJ / cm 2 More than 5,000mJ / cm 2 The tack was gone in less than. -: Accumulated light intensity 5,000mJ / cm 2 But Tuck stayed.

[0119] <Low molecular weight component content> The curable composition was applied to a polyester-based heavy release film (E7001, thickness 75 μm, manufactured by Toyobo Co., Ltd.) (hereinafter referred to as the heavy release film), and the film was laminated with a polyester-based light release film (E7002, thickness 50 μm, manufactured by Toyobo Co., Ltd.) (hereinafter referred to as the light release film) using a tabletop roll laminator (RSL-382S manufactured by Royal Sovereign) so as to avoid trapping air bubbles, to a film thickness of 20 μm, and then irradiated with ultraviolet light (high-pressure mercury lamp, illuminance 100 mW / cm2 , cumulative light intensity 5,000mJ / cm 2 ) Then, peel off the light release film and cut into 5cm pieces. 2 Three test pieces were cut out, dried at 90°C for 2 minutes, and weighed to obtain the mass of the cured film before extraction. 25 g of acetone and the weighed cured film were placed in a UV-opaque brown glass bottle, sealed, and rotated at 30°C for 48 hours to extract the soluble components in the cured film. The extracted solution was filtered through a 0.45 μm filter and subjected to HPLC analysis. The low molecular weight components were quantified based on the calibration curve, and the content of low molecular weight components was calculated using the following formula and evaluated as follows. Low molecular weight component content (%) = (mass of extracted low molecular weight components / mass of cured film before extraction) x 100% ++: The content of low molecular weight components was 1.0% or less. +: The content of low molecular weight components was more than 1.0% and 2.0% or less. ±: The content of low molecular weight components was more than 2.0% and 4.0% or less. -: The content of low molecular weight components was more than 4.0%.

[0120] <Light yellowing resistance> A heavy-release film was placed on a horizontally placed glass plate, and a silicone spacer (silicone will be used hereafter unless a specific material is specified) with an internal volume of 10 mm × 10 mm × 0.5 mm was placed on top of it. The curable composition was then filled into the spacer. A light-release film was placed over the liquid surface of the spacer to avoid trapping air bubbles, and ultraviolet light was irradiated from a UV-LED lamp (wavelength 405 nm, illuminance 100 mW / cm). 2 , cumulative light intensity 20,000mJ / cm 2 Thereafter, the light release film was peeled off, and the cured product was removed from the spacer, and the product was visually observed and evaluated for light yellowing resistance according to the following criteria. ++: No yellowing was observed. +: Very slight yellowing was observed. ±: Yellowing was observed. -: Obvious yellowing was observed.

[0121] <Durability> Accumulated light intensity: 5,000mJ / cm 2 Cured products of the curable compositions were prepared in the same manner as in the evaluation of light yellowing resistance, except for the following changes: After that, they were left to stand in a thermo-humidistat chamber at a temperature of 40°C and a relative humidity of 50% for 168 hours, the surface of the cured products was visually observed for the presence or absence of bleeding out, and durability was evaluated according to the following criteria. ++: No bleeding out was observed. +: Very little bleeding was observed. ±: Slight bleed-out was observed. -: Severe bleeding was observed.

[0122] [Table 3-1]

[0123] [Table 3-2]

[0124] As is clear from the evaluation results in Tables 3-1 and 3-2, the curable compositions of each Example using the benzoylformamide derivative (D) of the present disclosure exhibited good compatibility and high curability not only with high-pressure mercury lamps but also with 385 nm and 405 nm light from UV-LED lamps. The cured products obtained in the Examples had a low content of low-molecular-weight components, were highly safe, and exhibited excellent resistance to photoyellowing and durability. Furthermore, D-20 (Example 66), which contained a mono-substituted benzoylformamide group, exhibited higher curability than D-3 (Example 60), which contained a di-substituted benzoylformamide group. D-40 (Example 86), which contained a urethane group, exhibited higher compatibility and curability than D-24 (Example 70), which did not contain a urethane group. For Ds with 10 (D-30 in Example 76), 7 (D-36 in Example 82), and 4 (D-40 in Example 86) atoms directly bonded between the nitrogen atom of the benzoyl formate amide group and the nitrogen atom of the nearest urethane group, the 7 and 4 atoms exhibited higher curability than the 10 atom number, with the 4 atom number exhibiting the highest curability. D-42 (Example 88) and D-43 (Example 89), which have a methoxy group on the benzene ring of the benzoyl formate amide group, exhibited higher curability than D-44 (Example 90), which does not have a methoxy group. Furthermore, D-22 (Example 68), D-23 (Example 69), D-27 (Example 73), D-28 (Example 74), D-33 (Example 79), and D-40 (Example 86), which have urethane groups with molecular weights of less than 1,000, exhibited good compatibility. Furthermore, D-29 (Example 75), D-32 (Example 78), D-34 (Example 80), D-35 (Example 81), D-45 to D-49 (Examples 91 to 95), D-48, D-52 (Example 98), and D-53 (Example 99), which have urethane groups and polyol-derived alkylene structural units, polyether structural units, polyester structural units, polycarbonate structural units, polyolefin structural units, and polysiloxane structural units with molecular weights of 1,000 or more, showed good compatibility despite their high molecular weights. The cured products obtained in these examples had low contents of low molecular weight components, and the cured products had high light yellowing resistance and durability.On the other hand, Comparative Example 1, which used Esacure KIP 150 (E-1) as the photopolymerization initiator, exhibited poor curing properties with 405 nm light, with residual (unpolymerized) polymerizable compound (h) and decomposition products resulting from intramolecular cleavage of E-1 remaining in the cured product, resulting in a high content of low-molecular-weight components. Comparative Example 2, which used methyl benzoylformate (E-2), and Comparative Example 3, which used 2,4,6-trimethylbenzoyldiphenylphosphine oxide (E-3), were able to cure with 405 nm light, but because E-2, with a molecular weight of 164, itself is a low-molecular-weight component, and E-3 is an intramolecular-cleavage photopolymerization initiator, the cured products of Comparative Examples 2 and 3 both had high contents of low-molecular-weight components. Furthermore, the cured products of Comparative Examples 1 to 3 exhibited poor photoyellowing resistance and durability.

[0125] Examples 101 to 137 and Comparative Examples 4 to 10 (Preparation and Evaluation of Photoradical Polymerizable Active Energy Ray-Curable Compositions) The benzoylformamide derivatives (D-2) to (D-57) obtained in each example and the commercially available photosensitizers (I-3) and (I-4) for comparison were used. The monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and radical photopolymerization initiator (E) were weighed out in the compositions shown in Tables 4-1 and 4-2 and mixed at 25°C for 30 minutes to prepare photoradical polymerization active energy ray-curable compositions (hereinafter also referred to as radical curable compositions). The compatibility of the resulting radical curable compositions, their curability at different wavelengths of light, and the photoyellowing resistance and durability of the resulting cured products were evaluated using methods similar to those used to evaluate the curable compositions described above. The results are shown in Tables 4-1 and 4-2. The higher the curability of the curable composition, the higher the photosensitivity (sensitivity) of D.

[0126] [Table 4-1]

[0127] [Table 4-2]

[0128] Examples 138 to 143 and Comparative Examples 11 to 15 (Preparation and Evaluation of Photoionically Polymerizable Active Energy Ray-Curable Compositions) Using the benzoylformamide derivative (D) obtained in each example and commercially available photosensitizers (I-3) to (I-5), the cyclic ether compound (h3), photoionic polymerization initiator (E-10) or (E-11), and other additives (k) were weighed out in the compositions shown in Table 5, and mixed at 25°C for 30 minutes to prepare photoionic polymerization active energy ray-curable compositions (hereinafter also referred to as ionic curable compositions). The compatibility of the resulting ionic curable compositions and their curability with light of different wavelengths, as well as the photoyellowing resistance and durability of the resulting cured products, were evaluated using the methods described below, and the results are shown in Table 5. The higher the curability of the curable composition, the higher the photosensitivity of D.

[0129] <compatibility> The compatibility of the photoionically polymerizable curable composition was evaluated using the same method and criteria as in the evaluation of the compatibility of the photoradical polymerizable curable composition.

[0130] <Curability> As in the evaluation of the curability of the photoradical polymerization curable composition described above, a coating film with a thickness of 20 μm was prepared on a PET film and irradiated with active energy rays under the following conditions using various light sources 4) to 6) below. The coating was then left to stand in a thermostatic oven at 70°C for 1 hour to obtain a film-like cured product. The cumulative amount of light required for the surface of the resulting cured product to lose its tackiness when touched was determined, and the curability was evaluated according to the following criteria. The lower the cumulative amount of light required for the tackiness to disappear, the higher the curability. 4) High-pressure mercury lamp: wavelength 200-450nm, illuminance 500mW / cm 2 5) UV-LED lamp: wavelength 385 nm, illuminance 500 mW / cm 2 6) UV-LED lamp: wavelength 405 nm, irradiance 500 mW / cm 2 ++: Accumulated light intensity 5,000mJ / cm 2 The tack was gone in less than. +: Accumulated light intensity 10,000mJ / cm 2 The tack disappeared after irradiation. ±: Accumulated light intensity 50,000mJ / cm 2 The tack disappeared after irradiation. -: Accumulated light intensity 50,000mJ / cm 2 The tack remained even after irradiation.

[0131] <Light yellowing resistance> A photoionic cured product was prepared in the same manner as in the evaluation of the curability of the photoionic polymerization curable composition, except that the curing conditions were changed as follows: The photoyellowing resistance of the obtained cured product was evaluated in the same manner as in the evaluation of the photoyellowing resistance of the photoradical polymerization cured product. Curing conditions: UV-LED lamp: wavelength 405 nm, illuminance 1,000 mW / cm 2 , cumulative light intensity 100,000mJ / cm 2 After irradiation, the mixture was left standing at 70°C for 1 hour.

[0132] <Durability> Curing conditions: cumulative light intensity 50,000mJ / cm 2 A cured product was prepared in the same manner as for the photoionically polymerizable curable composition described above, except that irradiation was performed. The durability of the obtained cured product was evaluated in the same manner as for the photoionically polymerizable curable composition described above.

[0133] [Table 5]

[0134] Examples 144 to 151 and Comparative Examples 16 to 18 (Preparation of Photohybrid Polymerization-Based Active Energy Ray-Curable Compositions and Evaluation of Photosensitizers) The benzoyl formic acid amide derivative (D) synthesized in the examples and the commercially available photosensitizers (I-3) and (I-5) and the commercially available photopolymerization initiator (E-5) were used. The unsaturated compounds (h1), (h2), cyclic ether compounds (h3), and photoionic polymerization initiators (E-10) or (E-11), as well as other additives (k), were weighed in the proportions shown in Table 6. A photohybrid polymerization-based active energy ray-curable composition and cured product were obtained using the same method as in the evaluation of the photoionic polymerization-based photosensitizers described above. The compatibility and curability of the curable composition, as well as the photoyellowing resistance and durability of the cured product, were evaluated using the same method as in the evaluation of the photoionic polymerization-based photosensitizers described above. The results are shown in Table 6. The higher the curability of the curable composition, the higher the photosensitivity of D.

[0135] [Table 6]

[0136] As is clear from the results in Tables 4-1, 4-2, 5, and 6, the curable compositions of each Example using the benzoyl formic acid amide derivative (D) as a photosensitizer exhibited good compatibility. D exhibited photosensitivity to both the wide-range continuous light beam from a high-pressure mercury lamp and the 385 nm and 405 nm wavelength beams from a UV-LED lamp, and curable compositions containing D exhibited high curability. D was confirmed to have high photosensitivity even when used in combination with one or more photopolymerization initiators, including general-purpose photoradical polymerization initiators, general-purpose photoionic photopolymerization initiators, and photoradical polymerization initiator D. The photoradical, photoionic, and photohybrid curable compositions all exhibited high curability and were able to produce cured products with excellent photoyellowing resistance and durability. Furthermore, D-3 (Example 102), D-17 (Example 110), D-18 (Example 111), and D-41 to D-43 (Examples 127 to 129) containing methoxy groups exhibited extremely high photosensitization effects to light at 385 nm and 405 nm, clearly indicating that the inclusion of electron-donating methoxy groups shifted the absorption wavelength of D to longer wavelengths. D-55 to D-58 (Examples 140 to 143) containing cyclic epoxy groups exhibited photosensitization to photoionic polymerization initiators and were simultaneously incorporated into cured products via photoionic polymerization, resulting in high curability of the curable compositions and the production of highly durable cured products. Examples 144, 145, and 147 to 151 were photohybrid polymerization systems combining photoradical polymerization and photoionic polymerization, using a photoionic polymerization initiator and D in combination. In these examples, the curable compositions also exhibited high curability, and the resulting cured products exhibited good photoyellowing resistance and durability. That is, it was confirmed that D is effective both as a photoradical polymerization initiator and as a photosensitizer for photoionic polymerization. On the other hand, in Comparative Examples 4 to 8, 11, and 16, which did not use a photosensitizer, the sensitivity to light with wavelengths of 385 nm and 405 nm was low, and the curable compositions had poor curability. In Comparative Examples 9 and 10, which used isopropylthioxanthone (I-3) and 2-ethylanthraquinone (I-4) as photosensitizers, the curable compositions had good curability, but the photoyellowing resistance and durability of the resulting cured products were poor. In the ionic and hybrid comparative examples, similar results to those of the radical systems were confirmed.In Comparative Examples 15 and 18, which used polymeric thioxanthone (I-5), the photosensitivity was lower than when the low molecular weight I-3 was used, the curable compositions were less curable, yellowing of the obtained cured products was observed, and the durability of the cured products was low.

[0137] Examples 152 to 161 and Comparative Examples 19 to 21 (Active Energy Ray-Curable Ink Compositions and Evaluations Thereof) Benzoylformamide derivative (D), curable composition (F) containing D, commercially available photopolymerization initiator (E), curable composition (G) containing E, monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and other components (k) were weighed out according to the proportions (solids content) listed in Table 7 and mixed at 25°C for 30 minutes to obtain an active energy ray-curable ink composition (hereinafter also referred to as ink composition). The viscosity and curability of the ink composition were evaluated using the following methods. Inkjet printing was also performed using the ink composition, and the printability was evaluated using the following methods: ink ejection stability, blocking resistance, clarity, and bleed-out resistance. Furthermore, cured products for evaluating the low-molecular-weight component content were prepared using the ink composition, and the low-molecular-weight component content of the cured product of the ink composition was evaluated using the same method as for evaluating the low-molecular-weight component content of the cured product of the curable composition. The evaluation results are shown in Table 7.

[0138] <Viscosity> The viscosity of the ink composition was measured in accordance with ISO 2884-1 using a cone-plate viscometer (RE550 viscometer manufactured by Toki Sangyo Co., Ltd.) The viscosity of the ink composition for inkjet printing was evaluated according to the following four levels. ++: Viscosity was 5 mPa·s or more and less than 50 mPa·s. +: Viscosity was 50 mPa·s or more and less than 100 mPa·s. ±: Viscosity was 100 mPa·s or more and less than 200 mPa·s. -: Viscosity was 200 mPa·s or more.

[0139] <Method for producing printed matter by ultraviolet irradiation> The ink composition was applied to a PET film using a bar coater to form a coating film with a thickness of 20 μm, and then irradiated with ultraviolet light (UV-LED lamp: wavelength 395 nm, illuminance 1,000 mW / cm 2 ) and cured to produce a printed matter.

[0140] <Curability> When producing a printed matter, the integrated amount of light until the ink composition was completely cured (to a non-sticky state) was measured, and the curability of the ink composition was evaluated according to the following criteria. ++: Accumulated light intensity is 1,000mJ / cm 2 It was completely cured in less than 10 minutes. +: Accumulated light intensity 1,000mJ / cm 2 or more and 2,000mJ / cm 2 Completely cured in less than ±: Accumulated light intensity 2,000mJ / cm 2 or more and 5,000mJ / cm 2 It was completely cured in less than 10 minutes. -: The cumulative light dose required for complete curing is 5,000mJ / cm 2 More than this was necessary.

[0141] <Printability> The obtained ink composition was filled into an inkjet printer (LuxelJetUV350GTW, manufactured by Fujifilm Corporation), and a solid image was printed on coated paper to evaluate the ink ejection stability as printability.

[0142] <Discharge stability> The printing state of the printed matter was visually observed, and the ejection stability was evaluated according to the following criteria. ++: No nozzle missing and printing was good. +: There was a slight nozzle dropout. -: Nozzles were missing over a wide area.

[0143] <Blocking resistance> The printed material was left to stand for 5 minutes in an environment with a room temperature of 23°C and a relative humidity of 50%, and then a sheet of high-quality paper was placed on the printed surface and the material was subjected to a load of 1 kg / cm. 2The load was applied for 1 minute, and the degree of ink transfer to the paper was visually observed, and the blocking resistance was evaluated according to the following criteria. ++: The ink was dry and there was no transfer to the paper. +: The ink was dry and there was a small amount of transfer to the paper. ±: The ink was almost dry and was transferred to the paper. -: The ink hardly dried and there was a lot of transfer to the paper. <Clarity> The image clarity of the prints obtained from the ink compositions containing the pigments was visually observed and evaluated according to the following criteria. ++: No ink bleeding was observed and the image was clear. +: There was almost no ink bleeding and the image was good. -: Ink bleeding was observed.

[0144] <Bleed-out resistance> The printed material was left to stand in a thermo-hygrostat set at a temperature of 40°C and a relative humidity of 50% for 168 hours, and the surface of the printed material was visually observed and evaluated for bleed-out resistance according to the following criteria. ++: No bleeding out was observed. +: Slight bleeding out was observed. -: Severe bleeding was observed.

[0145] As is clear from the results in Table 7, the ink compositions of the Examples had high curability, and the resulting cured films (printed materials) were free of low-molecular-weight components. The cured films dried quickly and with little bleed-out, allowing for the production of highly durable printed materials. On the other hand, the ink composition of Comparative Example 19 had poor curability. Although curing was possible in Comparative Examples 20 and 21, the printed materials contained a large amount of low-molecular-weight components, resulting in poor blocking resistance, bleed-out resistance, and print clarity. Furthermore, Comparative Example 20, which used Esacure KIP 150 (E-1), had poor ink jetting stability and poor printability. Furthermore, the Examples containing pigments were able to produce clear printed materials. This is believed to be due to the pigments being uniformly dispersed or dissolved in the ink compositions of the Examples. Furthermore, the ink compositions of the Examples had low viscosity and high jetting stability, making them suitable for inkjet printing.

[0146] [Table 7]

[0147] Examples 162 to 170 and Comparative Examples 22 and 23 (Preparation and Evaluation of Active Energy Ray-Curable Pressure-Sensitive Adhesive Compositions) Benzoylformamide derivative (D), curable composition (F) containing D, commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and other components (k) were weighed out in the proportions (solids content) shown in Table 8 and mixed at 25°C for 30 minutes to prepare an active energy ray-curable pressure-sensitive adhesive composition (hereinafter also referred to as the pressure-sensitive adhesive composition). Pressure-sensitive adhesive sheets having adhesive layers were prepared using the pressure-sensitive adhesive composition by the following method, and the curability and adhesive strength of the pressure-sensitive adhesive composition to various substrates were evaluated. The resulting pressure-sensitive adhesive layers (cured products of the pressure-sensitive adhesive composition) were evaluated for low-molecular-weight component content, transparency, bleed-out resistance, reworkability, and photoyellowing resistance (using the same methods as those used to evaluate the curable compositions). The evaluation results are shown in Table 8.

[0148] <Curability> A heavy release film was adhered to a horizontally placed glass plate, a spacer 1 mm thick and 60 mm × 100 mm in size was placed, and the pressure-sensitive adhesive compositions prepared in Examples and Comparative Examples were filled inside the spacer. A light release film was placed on top of the filled composition, and the composition was irradiated with light at a wavelength of 405 nm and an illuminance of 100 mW / cm. 2 The UV-LED lamp provides an integrated light output of 1,000mJ / cm 2 The pressure-sensitive adhesive composition was cured by irradiating the adhesive so that the light release film was irradiated to a thickness of 100 μm. The light release film was then peeled off to obtain a pressure-sensitive adhesive sheet consisting of a cured product of the pressure-sensitive adhesive composition (adhesive layer) and the heavy release film. The curability of the pressure-sensitive adhesive composition was evaluated by touching the adhesive layer according to the following criteria. ++: A cured product was obtained that could maintain its shape, and no liquid deposits were observed. +: A hardened product that could maintain its shape was obtained, with only a small amount of liquid adhesion. ±: A cured product that could maintain its shape was obtained, and liquid adhesion was observed. -: Curing was insufficient, and a cured product that could not maintain its shape was obtained.

[0149] <Low molecular weight component content> The content of low molecular weight components in the resulting adhesive layer was evaluated in the same manner as in the evaluation of the content of low molecular weight components in the cured product of the curable composition.

[0150] <Transparency> The adhesive layer was transferred from the obtained adhesive sheet to a glass substrate in an environment of 23°C temperature and 50% relative humidity, and the total light transmittance of the glass substrate and adhesive layer was measured using a haze meter (NDH-8000, manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with ISO 14782. The transmittance of the glass plate was then measured in the same manner and subtracted from the total light transmittance of the glass substrate and adhesive layer to calculate the transmittance of the adhesive layer itself, and the transparency of the adhesive layer was evaluated according to the following criteria. ++: The transmittance was 90% or more. +: Transmittance was 85% or more and less than 90%. ±: The transmittance was 50% or more and less than 85%. -: Transmittance was less than 50%.

[0151] <Bleed-out resistance> The obtained pressure-sensitive adhesive sheet was left to stand for 168 hours in a thermo-hygrostat at a temperature of 40°C and a relative humidity of 50%, and then left to stand for 30 minutes in an environment at a temperature of 23°C and a relative humidity of 50%, and the bleed-out resistance of the pressure-sensitive adhesive layer was evaluated by touching the pressure-sensitive adhesive layer on the surface of the pressure-sensitive adhesive sheet according to the following criteria. ++: No liquid deposits were observed and no bleeding out was observed. +: There was very little liquid adhesion, and very little bleeding out was observed. ±: A small amount of liquid adhesion was observed, and a small amount of bleeding out was observed. -: Liquid adhesion was observed and bleeding out was observed.

[0152] <Adhesive strength> The adhesive layer was transferred from the resulting pressure-sensitive adhesive sheet to a film or plate substrate as described below under an environment of 23°C and 50% relative humidity, and then pressure-attached by rolling a 2 kg pressure roller back and forth twice. The adhesive was then left for 30 minutes under the same conditions. The 180° peel strength (N / 25 mm) (peel speed 300 mm / min) was then measured in accordance with ISO 29862 using a tensile tester (ORIENTE, Tensilon RTA-100, hereinafter also referred to as a universal testing machine), and the adhesive strength was evaluated according to the following criteria. PET2: Polyethylene terephthalate film (Cosmoshine A4160, corona treated, manufactured by Toyobo Co., Ltd.) PC: Polycarbonate (plate) (PC1600, manufactured by Takiron C.I. Co., Ltd.) GL: Glass (plate) (Eagle XG, Corning) ++: Peel strength was 20 (N / 25 mm) or more. +: Peel strength was 10 (N / 25 mm) or more and less than 20 (N / 25 mm). ±: Peel strength was 5 (N / 25 mm) or more and less than 10 (N / 25 mm). -: Peel strength was less than 5 (N / 25mm).

[0153] <Reworkability> As in the adhesive strength evaluation, the adhesive layer was transferred to a film or plate of a different substrate, pressed and attached, and left to stand for 24 hours in a thermostatic chamber at 80°C. After that, it was left for 30 minutes in an environment of 23°C temperature and 50% relative humidity, and the adhesive layer was peeled off, and the remaining state of the adhesive layer (glue) on the substrate surface was visually observed, and the reworkability of the adhesive layer was evaluated according to the following criteria. ++: No adhesive residue was left. +: There was a very small amount of glue remaining. ±: A small amount of adhesive was left behind. -: There was glue residue.

[0154] <Durability> The adhesive layer of the adhesive sheet was transferred to a glass substrate and left to stand in a thermo-hygrostat at a temperature of 85°C and a relative humidity of 85% for 100 hours, then left to stand in an environment at a temperature of 23°C and a relative humidity of 50% for 30 minutes, after which the condition of the adhesive layer was visually observed and durability was evaluated according to the following criteria. ++: The adhesive layer was transparent and had no lifting or bubbles. +: The adhesive layer was slightly cloudy, but there was no lifting or bubbles. -: The adhesive layer was cloudy or floating, and there were air bubbles.

[0155] [Table 8]

[0156] As is clear from the results in Table 8, the pressure-sensitive adhesive compositions of the Examples had high curability, and the adhesive layers obtained by curing them were highly transparent and had high adhesion (adhesive strength) to various substrates. Furthermore, the cured products (adhesive layers) obtained in the Examples had a low content of low-molecular-weight components, high bleed-out resistance, durability, and light-yellowing resistance, and also had good reworkability when the cured products were peeled from the substrate. On the other hand, the pressure-sensitive adhesive compositions of the Comparative Examples had low curability, a high content of low-molecular-weight components in the obtained cured products, low adhesive strength of the adhesive layers, and poor bleed-out resistance, durability, light-yellowing resistance, and reworkability.

[0157] Examples 171 to 177 and Comparative Examples 24 and 25 (Preparation and Evaluation of Active Energy Ray-Curable Adhesive Compositions) Benzoylformamide derivative (D), curable composition (F) containing D, commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and other components (k) were weighed according to the proportions (solids content) shown in Table 9 and mixed at 25°C for 30 minutes to prepare an active energy ray-curable adhesive composition (hereinafter also referred to as adhesive composition). The curability of the adhesive composition and the content of low molecular weight components in the resulting cured product were evaluated. In addition, various substrates were bonded using the adhesive composition to prepare laminates, and the adhesive strength and durability of the laminates were evaluated. The evaluation results are shown in Table 9.

[0158] <Curability> A PET film was placed on a horizontally placed glass plate, and the adhesive compositions of the Examples and Comparative Examples were applied to a thickness of 20 μm using a bar coater. A light-release film was then placed on top of the PET film, and the wavelength was 405 nm and the illuminance was 50 mW / cm. 2 The adhesive composition was cured by irradiating it with ultraviolet light from a UV-LED lamp. The light release film was then removed, and the presence or absence of tackiness on the surface of the cured film was confirmed. The curability of the adhesive composition was evaluated according to the following criteria based on the integrated amount of light required until the tackiness disappeared. ++: Accumulated light intensity 500mJ / cm 2 The tack was gone in less than. +: Accumulated light intensity 500mJ / cm 2 More than 1,000mJ / cm 2 The tack was gone in less than. ±: Accumulated light intensity 1,000mJ / cm 2 More than 5,000mJ / cm 2 The tack was gone in less than. -: Accumulated light intensity 5,000mJ / cm 2 But Tuck stayed.

[0159] <Laminate production> The adhesive composition was coated onto the various film- or plate-shaped substrates (substrates) shown below, and then laminated with a PET film using a tabletop roll laminator (RSL-382S) taking care not to trap air bubbles, so that the adhesive layer was 20 μm thick. The resulting laminate was then irradiated with ultraviolet light (wavelength 405 nm, illuminance 50 mW / cm).2 UV-LED lamp, cumulative light output: 2,000mJ / cm 2 ) to prepare a laminate. Base material (substrate) PET3: Polyethylene terephthalate film (Cosmoshine E5100, corona treated, manufactured by Toyobo Co., Ltd.) PMMA: Polymethyl methacrylate (plate) (COMOGLASS P, manufactured by Kuraray Co., Ltd.) PC: Polycarbonate (plate) (PC1600, manufactured by Takiron C.I. Co., Ltd.)

[0160] <Adhesive strength> The 180° peel strength (N / 25 mm) (peel speed 300 mm / min) of the laminate was measured using a universal testing machine in accordance with ISO 29862, and the adhesive strength was evaluated according to the following criteria. ++: Peel strength was 20 (N / 25 mm) or more. +: Peel strength was 10 (N / 25 mm) or more and less than 20 (N / 25 mm). ±: Peel strength was 5 (N / 25 mm) or more and less than 10 (N / 25 mm). -: Peel strength was less than 5 (N / 25mm).

[0161] <Durability> In the same manner as in the evaluation of the curing properties of the adhesive composition, a cured product (adhesive layer) was prepared on a glass substrate (integrated light dose 2,000 mJ / cm 2 ) and left to stand in a thermo-hygrostat at a temperature of 85°C and a relative humidity of 85% for 100 hours, and then left to stand in an environment at a temperature of 23°C and a relative humidity of 50% for 30 minutes, after which the state of the laminate was visually observed and durability was evaluated according to the following criteria. ++: The laminate was transparent and had no peeling or bubbles. +: The laminate was slightly cloudy, but there was no peeling or bubbles. ±: The laminate was slightly cloudy or peeled off, and bubbles were present. -: The laminate was extremely cloudy or peeled off, and there were bubbles.

[0162] <Low molecular weight component content> In the same manner as in the evaluation of the curing properties of the adhesive composition, a cured product (adhesive layer) was prepared on a PET film (wavelength 405 nm, illuminance 50 mW / cm 2 UV-LED, cumulative light output: 2,000mJ / cm 2 ) and the resulting PET film with the adhesive layer was cut into 5 cm 2 The content of low molecular weight components in the adhesive layer was evaluated in the same manner as in the evaluation of the content of low molecular weight components in the cured product of the curable composition.

[0163] [Table 9]

[0164] As is clear from the results in Table 9, the adhesive compositions of the Examples had high curability, and the laminates (bonded bodies) obtained by curing them had high adhesive strength to both homogeneous and heterogeneous substrates. Furthermore, the content of low-molecular-weight components in the cured product (adhesive layer) was low, and the durability of the laminate was good. These adhesive compositions exhibited properties suitable for use as an adhesive. On the other hand, the adhesive compositions of the Comparative Examples had low curability, and a large amount of low-molecular-weight components remained in the adhesive layer, resulting in low adhesive strength and durability of the bonded body.

[0165] Examples 178 to 184 and Comparative Examples 26 and 27 (Preparation and Evaluation of Active Energy Ray-Curable Sealant Compositions) Benzoylformamide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and other components (k) were weighed out according to the proportions (solids content) listed in Table 10 and mixed at 25°C for 30 minutes to prepare an active energy ray-curable sealant composition (hereinafter also referred to as sealant composition). A cured product of the sealant composition was prepared, and the sealant composition's curability, transparency, moist heat yellowing resistance, water resistance, outgassing resistance, heat cycle resistance, and corrosion resistance were evaluated. The sealant composition's cured product was also evaluated for the content of low molecular weight components, as with the cured product of the curable composition. These evaluation results are shown in Table 10.

[0166] <Preparation of cured sealant composition> A spacer (30 mm x 15 mm x 3 mm) was set on a glass plate, and copper foil (5 mm long x 50 mm wide x 80 μm thick) was placed inside the spacer, and the prepared sealant composition was poured into it. After sufficient degassing, the spacer was irradiated with ultraviolet light (wavelength 405 nm, illuminance 500 mW / cm). 2 UV-LED lamp, cumulative light output: 1,000mJ / cm 2 ) to obtain a cured product of the sealant composition.

[0167] <Curability> The cured product was evaluated according to the following criteria to evaluate curability. ++: A cured product was obtained that was able to maintain its shape and was not tacky when touched. +: A cured product was obtained that was able to maintain its shape, and the cured product was tacky when touched. ±: A cured product was obtained that was able to maintain its shape, but liquid residue was found on contact with the cured product. -: Curing was insufficient, and a cured product that could not maintain its shape was obtained.

[0168] <Transparency> The cured product was left standing for 24 hours in an environment of 23°C temperature and 50% relative humidity, after which the transmittance of the cured product was measured using the same haze meter as above, and the transparency was evaluated according to the following criteria. ++: The transmittance was 90% or more. +: Transmittance was 85% or more and less than 90%. ±: The transmittance was 50% or more and less than 85%. -: Transmittance was less than 50%.

[0169] <Heat and humidity yellowing resistance> The cured product was left standing for 24 hours in an environment with a temperature of 23°C and a relative humidity of 50%, after which the transmission spectrum of the cured product was measured using a dedicated transmission color measuring device (TZ-6000, manufactured by Nippon Denshoku Industries Co., Ltd.) and recorded as the initial b value. The cured product was then left standing for 500 hours in a thermo-hygrostat set at a temperature of 85°C and a relative humidity of 85%, performing an accelerated test of humidity and heat yellowing resistance. After the test, the cured product was left standing for 24 hours in an environment with a temperature of 23°C and a relative humidity of 50%, and the transmission color was measured and recorded as the post-humid heat b value. The difference between the post-humid heat b value and the initial b value was recorded as the change Δb (Δb = post-humid heat b value - initial b value). The humidity and heat yellowing resistance of the cured product was evaluated according to the following criteria. ++: Both the initial b value and the b value after moist heat treatment were 0.2 or less, and Δb was 0.1 or less. +: Either the initial b value or the b value after moist heat treatment exceeded 0.2, but both were 0.5 or less, and Δb was 0.2 or less. ±: Either the initial b value or the b value after moist heat treatment exceeded 0.5, but both were 1.0 or less, and Δb was 0.3 or less. -: Either the initial b value or the b value after moist heat treatment exceeded 1.0, or Δb exceeded 0.3.

[0170] <Water resistance> A 1g specimen was cut from the cured product and placed in a thermo-hygrostat at 85°C and 95% relative humidity for 48 hours, after which the specimen was weighed again. The water absorption was calculated using the following formula, and the water resistance was evaluated according to the following criteria. The lower the water absorption, the higher the water resistance of the cured product. Water absorption rate (%) = (weight after water absorption - weight before water absorption) / weight before water absorption × 100% ++: The water absorption rate was less than 1.0%. +: The water absorption rate was 1.0% or more and less than 2.0%. ±: The water absorption rate was 2.0% or more and less than 3.0%. -: Water absorption rate was 3.0% or more.

[0171] <Outgassing resistance> A 1g specimen was cut from the cured product and placed in a thermostatic chamber set at 100°C as a test piece. A dry nitrogen stream was passed through the specimen for 24 hours, after which the specimen was weighed again. The outgassing rate was calculated using the following formula, and the outgassing resistance was evaluated according to the following criteria. The lower the outgassing rate, the higher the outgassing resistance. Outgassing rate (%) = (weight after test - weight before test) / weight before test x 100% ++: The outgassing rate was less than 0.1%. +: The outgassing rate was 0.1% or more and less than 0.2%. ±: The outgassing rate was 0.2% or more and less than 0.3%. -: The outgassing rate was 0.3% or more.

[0172] <Heat cycle resistance> One heat cycle consisted of leaving the cured product at -40°C for 30 minutes and then leaving it at 100°C for 30 minutes, and the cured product was subjected to 100 cycles. After that, the cured product was visually observed and its heat cycle resistance was evaluated according to the following criteria. ++: No change was observed. +: A small amount of bubbles were observed, but neither cloudiness nor cracks were observed. ±: Some bubbles or cracks were observed, and there was slight cloudiness. -: Bubbles or cracks were observed all over the surface, and the product was translucent.

[0173] <Corrosion resistance> After the above-mentioned wet heat yellowing resistance test, the surface of the copper foil was visually observed, and the corrosion resistance of the cured product was evaluated according to the following criteria: The lower the corrosion of the copper foil, the lower the metal corrosiveness of the cured product and the higher the corrosion resistance of the cured product. ++: No corrosion occurred on the copper foil in the cured product. +: Slight corrosion was observed on the copper foil in the cured product. ±: Slight corrosion was observed on the copper foil in the cured product. -: There was significant corrosion of the copper foil in the cured product.

[0174] [Table 10]

[0175] As is clear from the results in Table 10, the sealant compositions of the Examples had high curability, the content of low-molecular-weight components in the resulting cured products (sealants) was low, and the cured products had high transparency, high resistance to moist heat yellowing, and water resistance, little outgassing, and good heat cycle resistance and corrosion resistance. On the other hand, the sealant compositions of the Comparative Examples had low curability, and a large amount of low-molecular-weight components remained in the sealant, and the sealant was unsatisfactory in two or more of the physical properties of transparency, resistance to moist heat yellowing, water resistance, outgassing resistance, heat cycle resistance, and corrosion resistance.

[0176] Examples 185 to 192 and Comparative Examples 28 and 29 (Preparation and Evaluation of Active Energy Ray-Curable Coating Compositions) According to the proportions (solid content equivalent) shown in Table 11, the benzoyl formic acid amide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and other components (k) were weighed and mixed at 25 ° C. for 30 minutes to prepare an active energy ray-curable coating composition (hereinafter also referred to as coating composition). Using the coating composition, a coating layer was produced by the following method, and the curability of the coating composition, adhesion of the obtained coating layer, photo-yellowing resistance, flex resistance, chemical resistance, scratch resistance, durability, and low molecular weight component content were evaluated. The results are shown in Table 11.

[0177] <Curability> The curability of the coating composition was evaluated using the same method and criteria as for the adhesive composition.

[0178] <Coating layer creation> A PET film was placed on a horizontally placed glass plate, and the coating compositions of the Examples and Comparative Examples were applied to a thickness of 5 μm using a bar coater. The coating compositions were then coated in a nitrogen atmosphere using a UV-LED lamp with a wavelength of 385 nm at an illuminance of 500 mW / cm. 2 , cumulative light intensity 2,000mJ / cm 2 A coating layer was formed on the PET film by irradiating the film with ultraviolet light.

[0179] <Adhesion evaluation> Test pieces were prepared by cutting 100 1 mm x 1 mm squares into the surface of the coating layer using a cutter knife in accordance with the cross-cut method described in ISO 2409. Commercially available cellophane tape was applied to the test piece and then peeled off, and the number of squares remaining on the test piece was counted and the adhesion was evaluated according to the following criteria. ++: 100 squares remain. +: 90 to 99 squares remain. -: There were 89 or fewer remaining squares.

[0180] <Light yellowing resistance> The photo-yellowing resistance of the cured product of the curable composition was evaluated using a UV-LED (wavelength 405 nm, illuminance 100 mW / cm 2 , cumulative light intensity 20,000mJ / cm 2 ) was used to irradiate the coating layer with ultraviolet light, and the resistance to yellowing of the coating layer from light was evaluated.

[0181] <Bending resistance> The specimen was bent while in contact with a mandrel (10 mmφ) so that the coating layer was on the outside, according to the cylindrical mandrel method described in ISO 1519. Thereafter, the coating layer was visually observed, and the bending resistance was evaluated according to the following criteria. ++: No whitening or cracking at the bent portion. +: Part of the folded part was whitened. ±: Part of the bent part was cracked. -: The bent part cracked.

[0182] <Chemical resistance> Using the prepared coating layer, oleic acid was applied to the surface of the coating layer to a diameter of approximately 1 cm, and after keeping it at 23°C for 1 hour, it was washed off with a neutral detergent.The surface condition was visually observed and the chemical resistance was evaluated according to the following criteria. ++: No trace of oleic acid was found. +: A slight trace of very thin whitening was observed in the area where oleic acid was applied. ±: The area where oleic acid was applied turned white and swelling was observed on the surface. -: The area where oleic acid was applied became sticky and surface peeling was observed.

[0183] <Scratch resistance> The surface of the coating layer was scraped back and forth 10 times with steel wool (#0000, weight 100 g) in an environment of room temperature 23°C and humidity 50%, and the surface of the coating layer was visually observed and evaluated for scratch resistance according to the following criteria. ++: No scratches were observed on the coating layer. +: Slight fine scratches were observed in part of the coating layer. ±: Streaky scratches were observed throughout the entire coating layer. -: Peeling of the coating layer was observed.

[0184] <Durability> The durability of the coating layer was evaluated in the same manner as in the durability evaluation of the cured product of the adhesive composition.

[0185] <Low molecular weight component content> The light source has a wavelength of 385 nm and an illuminance of 1,000 mW / cm 2 UV-LED lamp with an integrated light output of 10,000mJ / cm 2 The content of low molecular weight components in the coating layer was evaluated in the same manner as in the evaluation of the content of low molecular weight components in the cured product of the curable composition, except that:

[0186] [Table 11]

[0187] As is clear from the results in Table 11, the coating compositions of the examples exhibited high curability with long-wavelength light, and the resulting cured products (coating layers) exhibited good adhesion, photo-yellowing resistance, flex resistance, chemical resistance, and durability. Such coating compositions had properties suitable for use as coatings for vehicles, indoor and outdoor use, and decorative coatings. On the other hand, the coating compositions of the comparative examples exhibited poor curability with long-wavelength light, and a large amount of low-molecular-weight components remained in the resulting coating layer, resulting in poor physical properties of the coating layer.

[0188] Examples 193 to 202 and Comparative Examples 30 and 31 (Preparation and Evaluation of Actinic Ray-Curable Ink Compositions for Three-Dimensional Modeling) According to the proportions (solids content) listed in Table 12, the benzoylformamide derivative (D), the curable composition (F) containing D, the commercially available photopolymerization initiator (E), the monofunctional unsaturated compound (h1), and the polyfunctional unsaturated compound (h2) were weighed and mixed at 25°C for 30 minutes to prepare an active energy ray-curable ink composition for three-dimensional modeling (hereinafter also referred to as the ink composition for three-dimensional modeling). The viscosity and curability of the ink composition for three-dimensional modeling were evaluated. Three-dimensional models were fabricated using the modeling method described below, and the cure shrinkage resistance and the content of low-molecular-weight components in the modeled models were evaluated. The strength, heat resistance, modeling accuracy, light yellowing resistance, and bleed-out resistance of the resulting models were evaluated. These evaluation results are shown in Table 12.

[0189] <Viscosity> The viscosity of the ink composition for three-dimensional modeling was measured using a cone-plate viscometer (RE550 type viscometer) in accordance with ISO 2884-1, and evaluated according to the following criteria. ++: Viscosity was 5 mPa·s or more and less than 500 mPa·s. +: Viscosity was 500 mPa·s or more and less than 2,000 mPa·s. -: Viscosity was 2,000 mPa·s or more.

[0190] <Curability> The light source has a wavelength of 405 nm and an illuminance of 5 mW / cm 2 The curability of the ink composition for three-dimensional modeling was evaluated in the same manner as for the curable composition, except that the UV-LED lamp was changed to

[0191] <Creating a modeled object> A heavy-duty release film was adhered to a horizontally placed glass plate, and a spacer with an internal size of 6 mm x 60 mm x 60 mm was placed on top of it. The ink compositions for three-dimensional modeling of each Example and Comparative Example were filled into the spacer so as to form a layer with a thickness of 0.3 mm. After leaving the spacer in a thermostatic chamber at 60°C for 1 minute, ultraviolet light (wavelength 405 nm, illuminance 5 mW / cm) was applied from a UV-LED lamp. 2 , cumulative light intensity 100mJ / cm 2 ) and cured. The ink composition for three-dimensional modeling was similarly filled (0.3 mm thick) on top of the cured film (first layer) inside the spacer and cured. The same procedure was repeated to obtain a total of 20 layers of cured material (6 mm × 60 mm × 60 mm). Ultraviolet light (wavelength 405 nm, illuminance 100 mW / cm) was applied using a UV-LED lamp. 2 , cumulative light intensity 2,000mJ / cm 2 ) was irradiated onto the cured product to obtain a post-cure processed shaped object.

[0192] <Low molecular weight component content> A test piece 0.5 mm thick was cut out from the shaped object and weighed out 0.5 g. The content of low molecular weight components in the shaped object was evaluated in the same manner as in the evaluation of the content of low molecular weight components in the cured product of the curable composition.

[0193] <Cure shrinkage resistance> The density of the ink composition for three-dimensional modeling was measured using a Gay-Lussac pycnometer in accordance with ISO 758. The density of the modeled object was measured using an electronic pycnometer (MDS-300 manufactured by Alpha Mirage Co., Ltd.) in accordance with ISO 1183-1. The cure shrinkage rate was calculated from the density of the ink composition for three-dimensional modeling and the density of the modeled object using the following formula, and the cure shrinkage resistance of the ink composition for three-dimensional modeling was evaluated according to the following criteria. The lower the cure shrinkage rate, the higher the cure shrinkage resistance. Curing shrinkage rate (%)=(Ds-Dl) / D1×100% (In the formula, Ds is the density of the modeled object, and Dl is the density of the ink composition for three-dimensional modeling.) ++: The cure shrinkage was less than 6%. +: The cure shrinkage rate was 6% or more and less than 7%. ±: The cure shrinkage rate was 7% or more and less than 8%. -: The cure shrinkage rate was 8% or more.

[0194] <Strength> The Shore D hardness of the molded object was measured in accordance with ISO 48, and the strength of the three-dimensional molded object was evaluated according to the following criteria. ++: Shore D hardness was 60 or more. +: Shore D hardness was 40 or more and less than 60. -: Shore D hardness was less than 40.

[0195] <Heat resistance> The glass transition temperature (Tg) of the molded object was measured using a differential scanning calorimeter (DSC-60plus, manufactured by Shimadzu Corporation), and the heat resistance of the molded object was evaluated according to the following criteria. ++: Tg was 60°C or higher. +: Tg was 40°C or higher and lower than 60°C. -: Tg was less than 40°C.

[0196] <Modeling precision> The side surfaces of the molded object were visually observed and the height of the molded object was measured. These results were combined to evaluate the molding accuracy according to the following criteria. ++: The height was less than 6 mm ± 0.1 mm and there were no irregularities on the side. +: The height was 6mm ±0.1mm or more but less than ±0.2mm, or there was slight unevenness on the side. ±: The height was 6mm±0.2mm or more but less than ±0.3mm, or the side was slightly uneven. -: The height was 6mm±0.3mm or more, or there were obvious unevenness on the side.

[0197] <Light yellowing resistance> Further irradiate the object with ultraviolet light (UV-LED lamp, wavelength 405 nm, 100 mW / cm 2 , cumulative light intensity 20,000mJ / cm 2 ) and the resistance to yellowing of the shaped object to light was evaluated in the same manner as for the resistance to yellowing of the cured product of the curable composition.

[0198] <Bleed-out resistance> After leaving the molded object in a constant temperature and humidity chamber at a temperature of 40°C and a relative humidity of 50% for 168 hours, the side of the molded object was visually observed and the bleed-out resistance of the molded object was evaluated in the same manner as the bleed-out resistance of the ink composition cured film.

[0199] [Table 12]

[0200] As is clear from Table 12, the ink compositions for three-dimensional modeling of the Examples had high curing properties with respect to long-wavelength light, low shrinkage during curing, and high modeling precision for the resulting models. Furthermore, the models obtained in the Examples had high strength and heat resistance, and good bleed-out resistance and light-yellowing resistance. On the other hand, the ink compositions for three-dimensional modeling of the Comparative Examples had poor curing properties and low modeling precision for the resulting models. The models of the Comparative Examples contained many low-molecular-weight components, and the strength, heat resistance, and light-yellowing resistance of the models were unsatisfactory, with particularly poor bleed-out resistance.

[0201] Examples 203 to 208 and Comparative Examples 32 and 33 (Preparation and Evaluation of Active Energy Ray-Curable Nail Cosmetic Compositions) Benzoylformamide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), photosensitizer (I), and other component (k) were weighed out according to the proportions (based on solids) shown in Table 13 and mixed for 30 minutes at 25°C to prepare an active energy ray-curable nail cosmetic composition (hereinafter also referred to as the nail cosmetic composition). The curability of the nail cosmetic composition, adhesion to nylon substrates, surface hardness, surface gloss, and photoyellowing resistance of the resulting cured film, and the content of low-molecular-weight components in the cured film were evaluated, and the results are shown in Table 13.

[0202] <Curability> The nail cosmetic composition was applied to a nylon 6 test piece (SHT-N6(NC) manufactured by Toray Plastics Precision Co., Ltd.) using a separator to a film thickness of 100 μm. A cured film was produced by irradiating with ultraviolet light using a UV-LED lamp for gel nails (manufactured by Beauty Nailer, wavelength 405 nm, output 48 W). The time required for the tackiness to disappear when touching the surface of the cured film was measured, and curability was evaluated according to the following criteria. The shorter the time required for the tackiness to disappear, the higher the curability. ++: The tack was gone in under a minute. +: The tack disappeared in more than 1 minute but less than 3 minutes. ±: The tack disappeared in more than 3 minutes but less than 10 minutes. -: The tack did not disappear even after 10 minutes or more.

[0203] <Adhesion> The nail cosmetic composition was applied to a nylon substrate in the same manner as in the curing evaluation, and a cured film was produced by irradiating it for 3 minutes using a UV-LED lamp for gel nails. The adhesion of the resulting cured film was evaluated in accordance with ISO 2409 in the same manner as in the evaluation of coating layer adhesion of coating compositions.

[0204] <Surface hardness> A cured film was prepared in the same manner as in the adhesion evaluation, and a 750 g load of an HB hardness pencil was pressed against the surface of the film at a 45° angle and pulled, and changes in the film surface were confirmed visually, and the surface hardness was evaluated according to the following criteria: The fewer scratches and peeling that occurred on the film surface, the higher the surface hardness. +: No scratches or peeling occurred. ±: No peeling occurred, but scratches occurred. -: Peeling occurred.

[0205] <Surface gloss> Cured films were prepared in the same manner as in the adhesion evaluation and left to stand for 24 hours in a thermo-hygrostat chamber at a temperature of 40°C and a relative humidity of 50%. Thereafter, the gloss of the film surface was visually observed, and the surface gloss of the cured film was evaluated according to the following criteria. +: It was shiny. ±: Light reflection was observed, but there were cloudy areas. -: No light reflection was observed and there was no gloss.

[0206] <Low molecular weight component content> A cured film was prepared in the same manner as in the adhesion evaluation, and a nylon 6 test piece having the obtained cured film was used to evaluate the low molecular weight component content in the cured film in the same manner as in the evaluation of the low molecular weight component content in the cured product (adhesive layer) of the adhesive composition.

[0207] <Light yellowing resistance> A cured film was prepared in the same manner as in the adhesion evaluation, and set in a xenon fade meter with an intensity of 70 mW / cm 2 After that, the color change of the cured film was visually observed, and the light yellowing resistance was evaluated according to the following criteria. ++: No yellowing was observed. +: Very slight yellowing was observed. ±: Yellowing was observed. -: Obvious yellowing was observed.

[0208] [Table 13]

[0209] As is clear from the results in Table 13, the nail cosmetic compositions of the examples exhibited high curability using a UV lamp for gel nails, and the resulting cured films exhibited high adhesion to nylon substrates (materials containing numerous amide bonds, similar to nails, which are primarily composed of proteins). These nail cosmetic compositions were found to be suitable for use as a gel nail base gel to be applied directly to nails. Furthermore, the cured film contained a low content of low-molecular-weight components, ensuring safety. The cured film exhibited good surface gloss, surface hardness, and light-induced yellowing resistance, making it suitable for use as a top coat for gel nails. In contrast, the nail cosmetic compositions of the comparative examples exhibited poor curability, contained many low-molecular-weight components in the resulting cured film, and exhibited poor adhesion, surface hardness, surface gloss, and light-induced yellowing resistance.

[0210] Examples 209 to 214 and Comparative Examples 34 to 36 (Preparation and Evaluation of Active Energy Ray-Curable Dental Material Compositions) Benzoylformamide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), and other components (k) were weighed according to the proportions (solid content basis) shown in Table 14 and mixed at 25°C for 30 minutes to prepare an active energy ray-curable dental material composition (hereinafter also referred to as the dental material composition). The solubility (dispersibility), storage stability, and curability of the dental material composition were evaluated. The dental material composition was cured to obtain a cured product. The low molecular weight component content, hardness, surface smoothness, and bending strength of the cured product were evaluated, and the results are shown in Table 14.

[0211] <Solubility (dispersibility)> The state of the dental material composition was visually observed, and the solubility (dispersibility) was evaluated according to the following criteria. +: The obtained composition was in a homogeneous state. ±: The obtained composition was found to be slightly non-uniform. -: The obtained composition was inhomogeneous.

[0212] <Storage stability> The dental material composition was placed in a light-shielding screw tube, the lid was closed, and the composition was stored under two conditions: at 40° C. for 1 month and at 80° C. for 2 weeks. The state of dissolution or dispersion of the composition after storage was confirmed, and the storage stability was evaluated according to the following criteria. +: No change in condition was observed after storage at 40°C for one month and at 80°C for two weeks. Changes in condition were confirmed after storage at either 40°C for one month or 80°C for two weeks. -: Changes in condition were observed after storage under both conditions: 1 month at 40°C and 2 weeks at 80°C.

[0213] <Curability> The dental material composition was filled into a polytetrafluoroethylene mold (20 mm × 20 mm × 10 mm) with a hole of 6 mm diameter in the center, and the mold was pressed with a polypropylene film. 2The polypropylene film was peeled off and the cured product was touched with a hand to evaluate the curability according to the following criteria. ++: No stickiness at all. +: There was some stickiness, but no finger marks were left on the surface. ±: Sticky and finger marks left on the surface. -: It was so sticky that my fingers stuck to the surface.

[0214] <Low molecular weight component content> The cured product obtained in the curability evaluation was used to evaluate the content of low molecular weight components in the dental material composition cured product in the same manner as in the evaluation of the content of low molecular weight components in the hardenable composition.

[0215] <Hardness> The surface of the cured product obtained in the curability evaluation was buffed, and the Knoop hardness was measured using a microhardness tester (DMH-2, manufactured by Matsuzawa Seiki Co., Ltd.) at a temperature of 23°C, with a load of 100 gf applied for 20 seconds, and the hardness was evaluated according to the following criteria. ++: Knoop hardness was 200 KHN or more. +: Knoop hardness was 70 KHN or more and less than 200 KHN. -: Knoop hardness was less than 70KHN.

[0216] <Surface smoothness> The surface of the cured product obtained in the curability evaluation was visually observed, and the surface smoothness was evaluated according to the following criteria. ++: The surface was smooth and shiny. +: The surface was almost smooth, with slight cloudiness or irregularities observed. ±: The surface was cloudy overall, and some irregularities or granularity were observed. -: The entire surface was cloudy and covered with granular material.

[0217] <Bending strength> A heavy-duty release film was placed on a horizontally placed glass plate, and a polytetrafluoroethylene spacer (2 mm × 2 mm × 25 mm) was placed on top of it. The dental material composition was then filled in. A light-duty release film was placed over the liquid surface of the spacer to prevent air bubbles from being trapped, and ultraviolet light was irradiated from a UV-LED lamp (wavelength 405 nm, illuminance 50 mW / cm). 2 , cumulative light intensity 1,500mJ / cm 2 The release films on both sides were then peeled off, and the cured product was removed from the spacer to prepare a test specimen. The test specimen was immersed in water at 37°C for 24 hours, and then subjected to a bending test using a universal testing machine. The test conditions were in accordance with ISO 4049, with a support distance of 20 mm and a crosshead speed of 1 mm / min. The bending strength was evaluated according to the following criteria. ++: The bending strength was 100 MPa or more. +: The bending strength was 90 MPa or more and less than 100 MPa. ±: The bending strength was 80 MPa or more and less than 90 MPa. -: The bending strength was less than 80 MPa.

[0218] [Table 14]

[0219] As is clear from the results in Table 14, the dental material compositions of the Examples had high solubility or dispersibility, and were excellent in curability and storage stability. The content of low-molecular-weight components in the resulting cured products was low, making them safe for use as dental materials. The hardness and flexural strength of the cured products were also high, and the surface smoothness was good. On the other hand, the dental material compositions of the Comparative Examples had low curability and insufficient solubility and storage stability. The content of low-molecular-weight components in the cured products was also high, raising safety concerns. The surface smoothness, hardness, and flexural strength of the cured products were low. The dental material composition of the present disclosure can be suitably used as a dental restorative material (composite resin for crowns, composite resin for filling dental cavities, composite resin for core construction, composite resin for filling and restoring), denture base resin, luting resin, luting material (resin cement, resin-added glass ionomer cement), dental adhesive (orthodontic adhesive, cavity application adhesive), denture base lining material, impression material, dental temporary sealing material, dental fissure sealant, resin block for CAD / CAM, temporary crown, or artificial tooth material.

[0220] Examples 215 to 220 and Comparative Examples 37 and 38 (Preparation and Evaluation of Active Energy Ray-Curable Photosensitive Compositions) Benzoylformamide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), thermal polymerization initiator (J), solvent (c), and other components (k) were weighed according to the proportions (solids content) listed in Table 15 and mixed at 25°C for 30 minutes to prepare an active energy ray-curable photosensitive composition (hereinafter also referred to as photosensitive composition). Photosensitive resins were produced using the photosensitive composition according to the method described below, and the sensitivity (curability) and storage stability of the resulting photosensitive resins were evaluated. Furthermore, patterned cured products were produced from the photosensitive composition, and the pattern-forming properties of the resulting cured products and the content of low-molecular-weight components in the cured products were evaluated. These results are shown in Table 15.

[0221] <Production of photosensitive resin> The photosensitive compositions of the examples and comparative examples were applied to a film thickness of 15 μm using a spin coater, and dried in an oven for 3 minutes. Thereafter, the film was irradiated with ultraviolet light (wavelength 405 nm, illuminance 0.5 mW / cm) for 3 minutes. 2, cumulative light intensity 90mJ / cm 2 ) to obtain a photosensitive resin (cured product). The photosensitive composition not containing the thermal polymerization initiator (J) was dried at 80°C. The photosensitive composition containing the thermal polymerization initiator (J) was dried at 40°C, irradiated with ultraviolet light, and then heat-treated in an oven at 130°C for 30 minutes.

[0222] <Sensitivity> The photosensitive resin was touched with a hand and the sensitivity was evaluated according to the following criteria. ++: No stickiness at all. +: There was some stickiness, but no finger marks were left on the surface. ±: Sticky and finger marks left on the surface. -: It was so sticky that my fingers stuck to the surface.

[0223] <Storage stability> The photosensitive resin was left to stand in a thermo-hygrostat at a temperature of 40°C and a relative humidity of 50% for 168 hours, and the surface of the photosensitive resin was visually observed to evaluate the storage stability according to the following criteria. The less bleed-out there was, the higher the storage stability. ++: No bleeding out was observed. +: Slight bleeding out was observed. -: Severe bleeding was observed.

[0224] <Low molecular weight component content> Photosensitive resin, size 5cm 2 Three test pieces were cut out and dried for 30 minutes at 130° C. Thereafter, the content of low molecular weight components in the photosensitive resin (cured product of the photosensitive composition) was evaluated in the same manner as in the evaluation of the content of low molecular weight components in the cured product of the curable composition.

[0225] <Production of Patterned Cured Product> Using a negative photomask (pattern mask), cured products of the photosensitive compositions of the Examples and Comparative Examples were produced in the same manner as in the production of the photosensitive resin. The negative photomask was then removed from the cured products, and the unexposed areas were removed with cyclopentanone to obtain patterned cured products.

[0226] <Pattern Formation> The pattern formability of the patterned cured product was evaluated according to the following criteria. ++: There was no distortion of the pattern or chipping of the edges. +: There was no distortion in the pattern, and there was only slight chipping at the edges. ±: There was slight distortion of the pattern and chipping at the edges. -: The pattern was distorted and the edges were chipped.

[0227] [Table 15]

[0228] As is clear from the results in Table 15, the photosensitive compositions of the Examples had high curability (sensitivity), and the cured products (photosensitive resins) obtained by curing them had high storage stability and a low content of low-molecular-weight components. Furthermore, the patterned cured products of the Examples obtained using a pattern mask had excellent pattern-forming properties. On the other hand, the photosensitive compositions of the Comparative Examples had low sensitivity, and the cured products obtained therefrom had a high content of low-molecular-weight components and poor storage stability. Furthermore, the patterned cured products of the Comparative Examples obtained using a pattern mask had poor pattern-forming properties.

[0229] Examples 221 to 227 and Comparative Examples 39 and 40 (Preparation and Evaluation of Active Energy Ray-Curable Hydrogel Compositions) Benzoylformamide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), ion-exchanged water, and other components (k) were weighed out according to the proportions (solid content basis) shown in Table 16 and mixed for 30 minutes at 25°C to prepare an active energy ray-curable hydrogel composition (hereinafter also referred to as the hydrogel composition). The compatibility and curability of the hydrogel composition were evaluated, and the appearance and low molecular weight component content of the resulting cured product (hydrogel) were also evaluated. The results are shown in Table 16.

[0230] <compatibility> The prepared hydrogel compositions were evaluated using the same method and criteria as in the evaluation of the compatibility of the active energy ray-curable composition.

[0231] <Curability> The hydrogel composition was applied to a PET film using a bar coater to a film thickness of 20 μm. The coating was cured by irradiating it with ultraviolet light under the conditions 7) to 9) below, and the cured product was touched to evaluate its curability according to the following criteria. 7) High-pressure mercury lamp: wavelength 200-450nm, illuminance 100mW / cm 2 , 1,000mJ / cm 2 8) UV-LED lamp: wavelength 385nm, illuminance 100mW / cm 2 , 1,000mJ / cm 2 9) UV-LED lamp: wavelength 405 nm, illuminance 100 mW / cm 2 , 1,000mJ / cm 2 ++: Gel was formed throughout and the mixture was in a slightly hard state. +: A gel was formed overall and the product was in a slightly soft state. ±: Partial gel formed. -: No gel was formed.

[0232] <Appearance of cured product> The appearance of the cured product obtained in the evaluation of curability under UV irradiation condition 9) was visually observed and evaluated according to the following criteria. +: No turbidity or phase separation. ±: No phase separation, but turbidity was observed. -: Turbidity and phase separation were observed.

[0233] <Low molecular weight component content> Using the cured product obtained in the curability evaluation under UV irradiation conditions in 9), the low molecular weight component content (excluding water) of the cured product (hydrogel) was evaluated in the same manner as in the evaluation of the low molecular weight component content of the cured product of the curable composition.

[0234] [Table 16]

[0235] As is clear from the results in Table 16, the hydrogel compositions of the Examples contained water-soluble or hydrophilic acroylmorpholine (h1-1), N-(2-hydroxyethyl)acrylamide (h1-7), or N-vinylpyrrolidone (h1-11), and water. They exhibited good compatibility and were in an aqueous solution state. The hydrogel compositions of the Examples had high curability, and the cured products obtained by curing them formed gels entirely (hydrogels). Furthermore, the cured products (hydrogels) had a low content of low-molecular-weight components and were highly safe. Such hydrogels are suitable for use as sanitary and medical materials. On the other hand, the hydrogel compositions of the Comparative Examples had low compatibility and curability, and were unable to form uniform hydrogels even when irradiated with ultraviolet light, making it impossible to evaluate the content of low-molecular-weight components. Furthermore, the Comparative Examples, which partially formed hydrogels, had a high content of low-molecular-weight components in the hydrogels.

[0236] Examples 228 to 234 and Comparative Examples 41 and 42 (Preparation and Evaluation of Active Energy Ray-Curable Aqueous Compositions) Benzoylformamide derivative (D), commercially available photopolymerization initiator (E), monofunctional unsaturated compound (h1), polyfunctional unsaturated compound (h2), ion-exchanged water, and other components (k) were weighed out according to the proportions (solids content) shown in Table 17 and mixed for 30 minutes at 25°C to prepare an active energy ray-curable aqueous composition (hereinafter also referred to as aqueous composition). The dispersibility and curability of the aqueous composition were evaluated, and the appearance and low molecular weight component content of the obtained cured product were also evaluated. The results are shown in Table 17.

[0237] <Dispersibility> The aqueous composition was allowed to stand in a thermostatic bath at 40°C for 24 hours, and then the state of the aqueous composition was visually observed, and the dispersibility was evaluated according to the following criteria. +: The aqueous composition was a stable, uniform emulsion. ±: The aqueous composition was partially aggregated and was an inhomogeneous emulsion. -: The aqueous composition was phase separated.

[0238] <Curability> A coating film of the aqueous composition was prepared in the same manner as in the evaluation of the curability of the curable composition, dried at 80° C. for 5 minutes, and then irradiated with ultraviolet light to evaluate the curability.

[0239] <Appearance of cured product> The cured product obtained in the curability evaluation under UV irradiation condition 3) was visually observed, and the appearance of the cured product was evaluated according to the following criteria. +: The cured product was neither cloudy nor phase separated. ±: The cured product was cloudy. -: Phase separation occurred in the cured product.

[0240] <Low molecular weight component content> Using the cured product obtained in the curability evaluation under UV irradiation condition 3), the content of low molecular weight components in the cured aqueous composition was evaluated in the same manner as in the evaluation of the content of low molecular weight components in the curable composition.

[0241] [Table 17]

[0242] As is clear from the results in Table 17, the aqueous compositions of the Examples had good dispersibility, were able to maintain a good emulsion state, and exhibited high curability even when exposed to long-wavelength light. The cured products obtained had a low content of low-molecular-weight components. On the other hand, the aqueous compositions of the Comparative Examples had poor dispersibility and curability, and the cured products obtained contained a large amount of low-molecular-weight components.

[0243] This disclosure includes the following content: (1) A benzoylformamide derivative having a benzoylformamide group represented by general formula (1). JPEG2026031575000031.jpg3364In formula, Q 1 ~Q 3 each independently represents a hydrogen atom, a substituent represented by any of the formulae (Chemical Formula 2) to (Chemical Formula 8), a halogen group, or a nitrile group, and is bonded to any of the 2- to 6-positions. JPEG2026031575000032.jpg11539R 1~R 10 each independently represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, or a cyclic alkenyl group having 3 to 18 carbon atoms; * indicates the binding position. (2) The benzoylformamide derivative according to (1) above, which is at least one compound represented by any one of general formulas (2) to (4). JPEG2026031575000033.jpg3564In formula, Q 1 ~Q 3 is the same as defined in general formula (1), B 1 represents a monovalent organic group which may have a hydrogen atom, a hydroxyl group, an amino group, a thiol group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, an imide group, an ethylenically unsaturated group, or a benzoylformamide group; B 2 represents a monovalent organic group which may have a hydroxyl group, an amino group, a thiol group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, an amide group, an imide group, a siloxane group, an ethylenically unsaturated group, or a benzoylformamide group. JPEG2026031575000034.jpg3677In formula, Q 1 ~Q 3 is the same as defined in general formula (1), B 3 represents an m-valent organic group which may have an ethylenically unsaturated group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group, or an imide group, R 11represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a cyclic alkenyl group having 3 to 18 carbon atoms, or an aryl group having 6 to 8 carbon atoms; R 12 represents a linear saturated divalent hydrocarbon group having 1 to 18 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 18 carbon atoms, a branched saturated or unsaturated divalent hydrocarbon group having 3 to 18 carbon atoms, an alicyclic saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a divalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group, m represents an integer of 1 to 10. JPEG2026031575000035.jpg4283In formula, Q 1 ~Q 3 is the same as defined in general formula (1), A 1 represents a divalent organic group which may have an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, a urea group, a siloxane group, an amide group, or an imide group, B 4 , B 5 may each independently have an ethylenically unsaturated group, an ether group, a thioether group, an ester group, a carbonate group, a urethane group, a thiourethane group, an isocyanurate group, an allophanate group, a urea group, a siloxane group, an amide group or an imide group, and B 4 , B 5 represents a monovalent organic group containing one or more ethylenically unsaturated bonds, R 13 represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a cyclic alkenyl group having 3 to 18 carbon atoms, or an aryl group having 6 to 8 carbon atoms; R 14represents a linear saturated trivalent hydrocarbon group having 1 to 8 carbon atoms, a linear unsaturated trivalent hydrocarbon group having 2 to 8 carbon atoms, a branched saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, an alicyclic saturated or unsaturated trivalent hydrocarbon group having 3 to 8 carbon atoms, a trivalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a trivalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group; R 15 represents a linear saturated divalent hydrocarbon group having 1 to 18 carbon atoms, a linear unsaturated divalent hydrocarbon group having 2 to 18 carbon atoms, a branched saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, an alicyclic saturated or unsaturated divalent hydrocarbon group having 3 to 8 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, or a divalent organic group in which any one or more carbon atoms or hydrogen atoms of these hydrocarbon groups have been substituted with an oxygen atom, a nitrogen atom, a sulfur atom, a hydroxyl group, a thiol group, or an amine group; n represents an integer of 1 to 100. (3) Q of the benzoylformamide group represented by general formula (1) 1 ~Q 3 are each independently a hydrogen atom, a substituent represented by formula (3), or a substituent represented by formula (6). (4) The benzoylformamide derivative according to any one of (1) to (3), which has one or more ethylenically unsaturated bonds in the molecule, and the ethylenically unsaturated bonds are one or more groups selected from a (meth)acrylate group, a (meth)acrylamide group, a vinyl group, a vinyl ether group, an alkyl vinyl ether group, an allyl group, a (meth)allyl ether group, a styryl group, and a maleimide group. (5) The benzoylformamide derivative according to any one of (2) to (4) above, wherein the ethylenically unsaturated bond is an acrylate group or an acrylamide group. (6) The benzoylformamide derivative according to any one of (2) to (5), which has one or more urethane groups in the molecule and has 3 to 20 atoms directly linked between the nitrogen atom of the benzoylformamide group and the nitrogen atom of the nearest urethane group. (7) The benzoylformamide derivative according to any one of (2) to (6), which has one or more urethane groups in the molecule and has 4 to 10 atoms directly linked between the nitrogen atom of the benzoylformamide group and the nitrogen atom of the nearest urethane group. (8) The benzoylformamide derivative according to any one of (2) to (7) above, wherein m in the benzoylformamide derivative represented by the general formula (3) is an integer of 1 to 4. (9) The benzoylformamide derivative according to any one of (2) to (8) above, wherein n in the benzoylformamide derivative represented by the general formula (4) is an integer of 2 to 50. (10) The benzoylformamide derivative according to any one of (2) to (9) above, wherein the ratio of the number (total) of urethane groups to the number (total) of benzoylformamide groups in the benzoylformamide derivative represented by the general formula (3) is 0.5 to 10.0. (11) The benzoylformamide derivative according to any one of (2) to (10), wherein the ratio of the number (total) of urethane groups to the number (total) of benzoylformamide groups in the benzoylformamide derivative represented by the general formula (4) is 2.0 to 15.0. (12) The benzoylformamide derivative according to any one of (1) to (11) above, which is a photopolymerization initiator. (13) The photopolymerization initiator according to (12) above, wherein the benzoylformamide group represented by the general formula (1) is a monosubstituted benzoylformamide. (14) The benzoylformamide derivative according to any one of (1) to (11) above, which is a photosensitizer for photoradical polymerization and / or a photosensitizer for photoionic polymerization. (15) An active energy ray-curable composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (16) An actinic ray-curable ink composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (17) An active energy ray-curable pressure-sensitive adhesive composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (18) An active energy ray-curable adhesive composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (19) An active energy ray-curable sealant composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (20) An active energy ray-curable photosensitive composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (21) An active energy ray-curable nail cosmetic composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (22) An active energy ray-curable dental material composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (23) An active energy ray-curable coating composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (24) An active energy ray-curable aqueous composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (25) An actinic ray-curable inkjet ink composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (26) An active energy ray-curable elastomer composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (27) An active energy ray-curable resin composition for decorative sheets, containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (28) An active energy ray-curable architectural coating composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (29) An active energy ray-curable medical device surface coating composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (30) An actinic ray-curable ink composition for three-dimensional modeling, containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (31) An actinic ray-curable flexographic ink composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (32) An actinic ray-curable offset ink composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (33) An actinic ray-curable screen ink composition containing the benzoylformamide derivative according to any one of (1) to (12) and (14). (34) A resin composition for an active energy ray-curable self-repairing material, containing the benzoylformamide derivative according to any one of (1) to (12) and (14).

[0244] As explained above, the benzoyl formic acid amide derivative (D) of the present disclosure exhibits high curability with ultraviolet light of various wavelengths, including long-wavelength ultraviolet light with wavelengths of 360 to 420 nm. In particular, it exhibits high photopolymerization initiation, photosensitization, and curability even when using UV-LED lamps with wavelengths of 385 nm, 395 nm, and 405 nm. Furthermore, the inclusion of a urethane group and an ethylenically unsaturated group in the molecule further improves these individual performances and effects of D. In particular, the inclusion of D having an ethylenically unsaturated group results in extremely low levels of low-molecular-weight components in the cured product, which is safe and has excellent adhesion to various materials, as well as various good physical properties such as surface hardness, photoyellowing resistance, durability, and transparency. The benzoyl formic acid amide derivative (D) of the present disclosure can be used in an active energy ray-curable ink composition, an active energy ray-curable inkjet ink composition, an active energy ray-curable flexographic ink composition, an active energy ray-curable offset ink composition, an active energy ray-curable screen ink composition, an active energy ray-curable nail cosmetic composition, an active energy ray-curable pressure-sensitive adhesive composition, an active energy ray-curable adhesive composition, an active energy ray-curable sealant composition, an active energy ray-curable coating composition, an active energy ray-curable resin composition for decorative sheets, an active energy ray-curable elastomer ... The active energy ray-curable compositions can be suitably used as active energy ray-curable ink compositions for three-dimensional modeling, active energy ray-curable vehicle coating compositions, active energy ray-curable nail cosmetic compositions, active energy ray-curable resin compositions for self-repairing materials, active energy ray-curable architectural coating compositions, active energy ray-curable compositions for various coating applications such as ship bottom paints, anti-fog materials, and antifouling paints, active energy ray-curable compositions for medical device surface coatings, active energy ray-curable dental material compositions, active energy ray-curable photosensitive compositions, active energy ray-curable hydrogel compositions, and active energy ray-curable aqueous dispersion compositions. Furthermore, the resulting hydrogel compositions and aqueous compositions can be suitably used as materials in a wide variety of fields, including the hygiene field (e.g., superabsorbent resins, disposable diapers, and soft contact lenses), the medical field (e.g., medical device surface coatings and artificial organs), the civil engineering and construction field (e.g., soil conditioners), the agricultural field (e.g., water-retaining materials), and impact-absorbing materials.

Claims

1. A composition containing a benzoylformamide derivative (A) and a polymerizable compound (B), A composition, wherein A has one or more benzoylformamide groups represented by general formula (1) in the molecule, and B is a compound having an ethylenically unsaturated group and / or a cyclic ether group. Q 1 ~Q 3 are each independently a hydrogen atom, a substituent represented by any of the formulae (Chemical Formula 2) to (Chemical Formula 8), a halogen group, or a nitrile group, and are bonded to any of the 2- to 6-positions. R 1 ~R 10 each independently represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a linear alkenyl group having 2 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, a branched alkenyl group having 3 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, or a cyclic alkenyl group having 3 to 18 carbon atoms; * indicates the bond position.

2. 2. The composition according to claim 1, wherein the benzoylformamide derivative (A) has at least one group selected from the group consisting of a hydroxyl group, an ethylenically unsaturated group, and a urethane group.

3. 3. The composition according to claim 1, wherein the benzoylformamide derivative (A) and / or the polymerizable compound (B) has an ethylenically unsaturated group.

4. the benzoylformamide derivative (A) and / or the polymerizable compound (B) have one or more ethylenically unsaturated groups in the molecule, 3. The composition according to claim 1, wherein the ethylenically unsaturated group is one or more groups selected from a (meth)acrylate group, a (meth)acrylamide group, a vinyl group, a vinyl ether group, an alkyl vinyl ether group, an allyl group, a (meth)allyl ether group, a styryl group, and a maleimide group.

5. the polymerizable compound (B) contains a monofunctional unsaturated compound having one ethylenically unsaturated group in the molecule, The monofunctional unsaturated compound is selected from the group consisting of alkyl (meth)acrylate, hydroxyalkyl (meth)acrylate, alkyloxyalkylene glycol (meth)acrylate, alkoxydialkylene glycol (meth)acrylate, alkoxytrialkylene glycol (meth)acrylate, alkoxypolyalkylene glycol (meth)acrylate, phenoxyalkylene glycol (meth)acrylate, phenoxydialkylene glycol (meth)acrylate, phenoxytrialkylene glycol (meth)acrylate, phenoxypolyalkylene glycol (meth)acrylate, N-alkylamino (meth)acrylate, N-alkylaminoalkyl (meth)acrylate, N,N-dialkylaminoalkyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyl ... Clopentenyloxyethyl (meth)acrylate, bornyl (meth)acrylate, isobornyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-methyl-2-adamantyl (meth)acrylate, N-(meth)acryloyloxyethyl norbornenecarboxamide, N-(meth)acroylmorpholine, diacetone (meth)acrylamide, N-alkyl (meth)acrylamide, N,N-dialkyl (meth)acrylamide, N-hydroxyalkyl (meth)acrylamide, N,N-di(hydroxyalkyl) (meth)acrylamide, N-hydroxyalkyl-N-(4-hydroxyphenyl) (meth)acrylamide, N-alkyl-N-hydroxyalkyl (meth)acrylamide, N-alkyl-N-(4-hydroxyphenyl) (meth)acrylamide, 4-hydroxyphenyl (meth)acrylamide, N,N-di(4-hydroxyphenyl) (meth)acrylamide, N-alkoxyalkyl (meth)acrylamide, N,One or more compounds selected from N-di(alkoxyalkyl)(meth)acrylamides, N-alkyl-N-alkoxyalkyl(meth)acrylamides, N-sulfoalkylacrylamides, N-alkylamino(meth)acrylamides, N-alkylaminoalkyl(meth)acrylamides, and N,N-dialkylaminoalkyl(meth)acrylamides, The composition according to claim 1 or claim 2, wherein the alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, and the alkylene is an alkylene group having 1 to 4 carbon atoms.

6. the polymerizable compound (B) contains a polyfunctional unsaturated compound having two or more ethylenically unsaturated groups in the molecule, The polyfunctional unsaturated compound is selected from the group consisting of allyl(meth)acrylate, allyloxyalkoxy(meth)acrylate, allyl(meth)acrylamide, allyloxyalkoxy(meth)acrylamide, vinyloxyalkoxy(meth)acrylate, alkylene glycol di(meth)acrylate, polyalkylene glycol di(meth)acrylate, bisphenol A diglycidyl ether (meth)acrylic acid adduct, alkoxylated bisphenol A di(meth)acrylate, polyester di(meth)acrylate, polycarbonate di(meth)acrylate, polyurethane di(meth)acrylate, polyurethane di(meth)acrylamide, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, and dipentaerythritol tri(meth)acrylate. the compound is one or more compounds selected from the group consisting of ethylene oxide-modified tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tri(meth)acryloyloxyethoxytrimethylolpropane, glycerin polyglycidyl ether poly(meth)acrylate, ethylene oxide-modified isocyanuric acid tri(meth)acrylate, ethylene oxide-modified dipentaerythritol penta(meth)acrylate, ethylene oxide-modified dipentaerythritol hexa(meth)acrylate, ethylene oxide-modified pentaerythritol tri(meth)acrylate, ethylene oxide-modified pentaerythritol tetra(meth)acrylate, and succinic acid-modified pentaerythritol tri(meth)acrylate, The composition according to claim 1 or claim 2, wherein the alkyl is a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms, and the alkylene is an alkylene group having 1 to 4 carbon atoms.

7. 3. The composition according to claim 1, further comprising one or more additives selected from the group consisting of a coinitiator, a photosensitizer, a curing accelerator, a thermal polymerization initiator, a photoradical polymerization initiator, a photoionic polymerization initiator, an organic solvent, water, a pigment dispersant, an inorganic filler, and a leveling agent.

8. 3. The composition according to claim 1, which is polymerizable by heat and / or light.

9. 3. The composition according to claim 1 or 2, which is used for one of the following purposes: ink, inkjet ink, ink for three-dimensional modeling, pressure-sensitive adhesive, adhesive, sealant, coating agent, photosensitive resin, nail cosmetic, dental material, and aqueous composition.

10. 3. An actinic ray-curable inkjet ink composition comprising the composition according to claim 1.

11. 3. An actinic ray-curable ink composition for three-dimensional modeling, comprising the composition according to claim 1.

12. 3. An active energy ray-curable pressure-sensitive adhesive composition comprising the composition according to claim 1.

13. 3. An active energy ray-curable adhesive composition comprising the composition according to claim 1.

14. 3. An active energy ray-curable sealant composition comprising the composition according to claim 1.

15. 3. An active energy ray-curable photosensitive composition comprising the composition according to claim 1.

16. 3. An active energy ray-curable nail cosmetic composition comprising the composition according to claim 1.

17. 3. An active energy ray-curable dental material composition comprising the composition according to claim 1.

18. 3. An active energy ray-curable coating composition comprising the composition according to claim 1.

19. 3. An active energy ray-curable aqueous composition comprising the composition according to claim 1.