Coating agent composition containing n-substituted (METH) acrylamide

Abstract

An object of the present invention is to provide a polymerizable composition which has excellent wettability to various substrates having a wide range of polarity from low polarity to high polarity, such as an organic substrate, an inorganic substrate, and a substrate formed of an organic-inorganic composite material, has high transparency and curability, and can provide a cured product having excellent water resistance by being cured, a polymer of the polymerizable composition, and a coating agent composition using the same.SOLUTION: The coating agent composition comprises a polymerizable composition containing an N-substituted (meth) acrylamide (A) represented by general formula [1] and / or a polymer thereof. (In the formula, R1 represents hydrogen or methyl, one of R2 and R3 represents a chain hydrocarbyl group having 6 or more carbon atoms or a cyclic hydrocarbyl group having 6 or more carbon atoms, and the other represents hydrogen, a chain hydrocarbyl group having 1 or more carbon atoms, or a cyclic hydrocarbyl group having 3 or more carbon atoms.). )

Description

[Technical Field]

[0001] The present invention relates to a coating composition containing an N-substituted (meth)acrylamide. [Background technology]

[0002] In recent years, N-substituted (meth)acrylamides have been widely used as raw material monomers for adhesives, adhesives for optical components, active energy curable adhesives for polarizing plates, inkjet inks, resin compositions for stereolithography, encapsulants for semiconductors and electronic materials, and coating agents for glass and resin molded products (Patent Documents 1 to 4). In particular, because the amide group has high cohesive strength, excellent adhesion to various substrates, and is not corrosive to metals or metal oxides, they have often been reported to be used as a substitute for (meth)acrylic acid (Patent Documents 5 to 7). However, many of the commonly used N-substituted (meth)acrylamides contain hydrophilic monomers that are soluble in water, and it has been pointed out that their water resistance is insufficient depending on the monomer content and the intended use of the resulting molded product.

[0003] Furthermore, although N-substituted (meth)acrylamides are often used as components of active energy ray-curable resins, no method has yet been proposed for improving the water resistance when they are incorporated into long-life products such as electronic materials and optical materials. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2008-287207 [Patent Document 2] Japanese Patent Application Laid-Open No. 2011-122013 [Patent Document 3] Japanese Patent Application Laid-Open No. 2001-310918 [Patent Document 4] Japanese Patent Application Laid-Open No. 2010-155889 [Patent Document 5] Japanese Patent Application Laid-Open No. 2011-137181 [Patent Document 6] Japanese Patent Application Laid-Open No. 2010-235646 [Patent Document 7] Japanese Patent Application Laid-Open No. 2013-256552 Summary of the Invention [Problem to be solved by the invention]

[0005] A first object of the present invention is to provide a polymerizable composition, a polymer of the polymerizable composition, etc., which has excellent wettability with various substrates, such as organic substrates, inorganic substrates, and substrates made of organic-inorganic composite materials, which have a wide range of polarities from low to high, and which has high transparency and curability, and which can provide a cured product having excellent water resistance when cured.A second object of the present invention is to provide a pressure-sensitive adhesive composition containing the polymerizable composition and / or a polymer thereof, which has adhesion and cohesive strength to various substrates and has high transparency, water resistance, stain resistance, yellowing resistance, and durability, and a laminate of an adhesive layer made of the pressure-sensitive adhesive composition and various substrates. a coating composition that has high wettability and adhesion to various substrates and exhibits high surface hardness and water resistance upon curing; a hair cosmetic that is moisture-resistant, smooth, and resistant to stickiness, has a good texture, and is stable over time; and an oil-in-water emulsion cosmetic composition that does not cause skin irritation and has excellent emulsion stability, usability, and stability over time; an ink that has high adhesion to various substrates, excellent printing properties such as pigment dispersibility, surface drying, ejection stability, and clarity, and has high curability, yellowing resistance, and water resistance; and an ink composition for three-dimensional modeling that can accurately model three-dimensional objects with high strength, heat resistance, and water resistance and has excellent resistance to curing shrinkage. [Means for solving the problem]

[0006] In light of the above, and as a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by a polymerizable composition containing an amphiphilic N-substituted (meth)acrylamide having a specific structure, which has at least one chain or cyclic hydrocarbon group having 6 or more carbon atoms as a hydrophobic group and a (meth)acrylamide group as a hydrophilic group, and have thus completed the present invention.

[0007] That is, the present invention provides: (1) A polymerizable composition containing an N-substituted (meth)acrylamide (A) represented by the general formula [1]: [ka] (In the formula, R 1 represents a hydrogen atom or a methyl group, and R 2 and R 3 one of the groups represents a chain hydrocarbon group having 6 or more carbon atoms or a cyclic hydrocarbon group having 6 or more carbon atoms, the other represents a hydrogen atom, a chain hydrocarbon group having 1 or more carbon atoms or a cyclic hydrocarbon group having 3 or more carbon atoms, and R 2 and R 3 includes those which, together with the nitrogen atom carrying them, form a saturated ring of six or more members. (2) The polymerizable composition according to (1), wherein the N-substituted (meth)acrylamide (A) is an N-monosubstituted (meth)acrylamide or an N,N-disubstituted (meth)acrylamide, and has, as a substituent, one or more structures selected from a chain saturated structure and an unsaturated structure and a cyclic saturated structure and an unsaturated structure having 6 to 36 carbon atoms; (3) The polymerizable composition according to (1) or (2), wherein the saturated water absorption of the cured product is 10% or less. (4) The surface tension of N-substituted (meth)acrylamide (A) is 24.0 to 46.0 mN m -1 The polymerizable composition according to any one of (1) to (3), (5) The polymerizable composition according to any one of (1) to (4), wherein the content of the N-substituted (meth)acrylamide (A) relative to the total weight of the polymerizable composition is 1% by weight or more. (6) A polymer obtained by polymerizing the polymerizable composition according to any one of (1) to (5) above with active energy rays and / or heat. (7) The polymerizable composition according to any one of (1) to (5), further comprising one or more selected from a polymerization initiator, a compound having an unsaturated bond (excluding N-substituted (meth)acrylamide (A) and a polymer using the same), a non-polymerizable oligomer and a non-polymerizable polymer (excluding a polymer using N-substituted (meth)acrylamide (A)), and the polymer according to (6). (8) A pressure-sensitive adhesive composition comprising the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above, or the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above and a crosslinking agent; (9) A laminate comprising an adhesive layer made of the adhesive composition according to (8) above and an organic and / or inorganic substrate, wherein the organic and / or inorganic substrate has a surface tension of 22.6 to 59.0 mN m-1. (10) An adhesive composition containing the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above and a crosslinking agent. (11) A polymerizable composition according to any one of (1) to (5) and (7) above, or a polymer according to (6) above, containing a crosslinking agent, wherein the absolute value of the difference in surface tension between two different adherends is 37.0 mN m -1 an adhesive composition comprising: (12) A cosmetic composition containing the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above. (13) A coating composition comprising the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above, or the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above and a crosslinking agent; (14) An ink composition comprising the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above, or the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above and a crosslinking agent. (15) An ink composition for use in three-dimensional modeling, comprising the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above, or the polymerizable composition according to any one of (1) to (5) and (7) above or the polymer according to (6) above and a crosslinking agent. This provides: [Effects of the Invention]

[0008] According to the present invention, a polymerizable composition containing an N-substituted (meth)acrylamide (A) of a specific structure has high transparency and good curability due to the well-balanced amphiphilicity of the N-substituted (meth)acrylamide (A), and it is possible to obtain a polymerizable composition and a polymer of the polymerizable composition that have excellent wettability to various substrates having a wide range of polarities, from low to high, including organic substrates, inorganic substrates, and organic-inorganic hybrid substrates. By containing the obtained polymerizable composition and / or a polymer thereof, it is possible to provide a pressure-sensitive adhesive composition that exhibits adhesion and cohesive strength to various substrates and has high transparency, stain resistance, yellowing resistance, and durability, as well as a laminate of an adhesive layer made of the pressure-sensitive adhesive composition and various substrates. Furthermore, by containing the polymerizable composition and / or a polymer thereof, the present invention can provide: an adhesive composition for homogeneous or heterogeneous materials that has high adhesion to various substrates, impact resistance, and water resistance; a hair cosmetic composition that is moisture-resistant, smooth, resistant to stickiness, has a good texture, and is stable over time; an oil-in-water emulsion cosmetic composition that does not cause skin irritation and has excellent emulsion stability, usability, and stability over time; a coating agent that has high wettability and adhesion to various substrates and exhibits high surface hardness and water resistance when cured; an ink that has high adhesion to various substrates, excellent printing properties such as pigment dispersibility, surface drying properties, ejection stability, and clarity, and has high curability and yellowing resistance; and an ink composition for three-dimensional modeling that can accurately model three-dimensional objects that have high strength, heat resistance, and water resistance, and has excellent resistance to curing shrinkage. DETAILED DESCRIPTION OF THE INVENTION

[0009] The first embodiment of the present invention is a polymerizable composition. The second embodiment is a polymer obtained by polymerizing the polymerizable composition of the first embodiment with active energy rays and / or heat. The third embodiment is a polymerizable composition in which the polymerizable composition of the first embodiment further contains one or more selected from a polymerization initiator, a compound having an unsaturated bond (excluding N-substituted (meth)acrylamide (A) and polymers using the same), a non-polymerizable oligomer and a non-polymerizable polymer (excluding polymers using N-substituted (meth)acrylamide (A)), and the polymer of the second embodiment. The fourth embodiment is a polymerizable composition in which the polymer of the second embodiment further contains one or more selected from a polymerization initiator, a compound having an unsaturated bond (excluding N-substituted (meth)acrylamide (A) and polymers using the same), a non-polymerizable oligomer and a non-polymerizable polymer (excluding polymers using N-substituted (meth)acrylamide (A)), and a crosslinker having two or more reactive functional groups in the molecule (excluding compounds having two or more unsaturated bonds in the molecule). The first to fourth embodiments of the present invention will be collectively described below.

[0010] The polymerizable composition according to the first embodiment of the present invention contains an N-substituted (meth)acrylamide (A) represented by the following general formula [1].

[0011] [ka]

[0012] In general formula [1], R 1 represents a hydrogen atom or a methyl group, and R 2 and R 3 one of the groups represents a chain hydrocarbon group having 6 or more carbon atoms or a cyclic hydrocarbon group having 6 or more carbon atoms, the other represents a hydrogen atom, a chain hydrocarbon group having 1 or more carbon atoms or a cyclic hydrocarbon group having 3 or more carbon atoms, and R 2 and R 3R includes those which, together with the nitrogen atom carrying them, form a saturated ring of six or more members. The saturated ring of six or more members may or may not contain a heteroatom. 2 and R 3 may or may not contain a heteroatom-containing substituent, and if it does contain one, the number of heteroatoms is three or less. The heteroatom refers to an oxygen atom, a sulfur atom, a nitrogen atom, or a boron atom. Note that N-substituted (meth)acrylamides not included in the general formula [1] are also referred to as N-substituted (meth)acrylamides (B).

[0013] A polymer according to a second embodiment of the present invention is a polymer obtained by polymerizing the polymerizable composition according to the first embodiment with active energy rays and / or heat. The polymer is a soluble polymer having no crosslinked structure, and may be a homopolymer of any one monomer selected from the N-substituted (meth)acrylamide (A), a copolymer of A obtained by copolymerizing two or more monomers selected from A in any proportion, or a copolymer obtained by copolymerizing one or more monomers selected from A in any proportion with copolymerizable monomers other than A. In addition, the copolymer obtained from the N-substituted (meth)acrylamide (A) and a monomer other than A preferably has a content of A in the copolymer of 1 wt % or more based on the total weight of the copolymer.

[0014] The N-substituted (meth)acrylamide (A) used in the first to fourth embodiments of the present invention (hereinafter collectively referred to as the present embodiment) is amphiphilic, and has a chain hydrocarbon group having 6 or more carbon atoms, a cyclic hydrocarbon group having 6 or more carbon atoms, and R 2 and R 3The polymerizable composition according to the present embodiment has at least one substituent selected from the group consisting of a six- or higher-membered saturated ring containing a nitrogen atom bearing a substituent, and a hydrophilic (meth)acrylamide group capable of imparting wettability to highly polar substrates. By containing the N-substituted (meth)acrylamide (A), the polymerizable composition according to the present embodiment exhibits good compatibility with the components constituting the composition, high transparency, and good wettability to various substrates, including organic substrates, inorganic substrates, and organic-inorganic hybrid substrates with a wide range of polarities, from low to high. Furthermore, since the N-substituted (meth)acrylamide (A) exhibits sufficient curability and polymerizability with active energy rays and / or heat, polymerizable compositions containing the N-substituted (meth)acrylamide (A) have high curability and polymerizability. Due to the synergistic effect of the good wettability to various substrates with a wide range of polarities and the strong cohesive force between the amide groups, pressure-sensitive adhesive compositions and adhesive compositions molded from the polymerizable composition containing the N-substituted (meth)acrylamide (A) and / or polymers obtained by polymerizing the polymerizable composition (hereinafter also referred to as polymers of the polymerizable composition or polymers) exhibit excellent adhesion to various substrates. Therefore, a pressure-sensitive adhesive composition having high adhesive strength and contamination resistance (reworkability), and an adhesive composition having high adhesive strength, impact resistance, and water resistance can be obtained as a molded article of the polymerizable composition and / or its polymer. By utilizing the properties of the N-substituted (meth)acrylamide (A) described above, the polymerizable composition and / or its polymer according to this embodiment can be applied to various uses, such as not only pressure-sensitive adhesive compositions and adhesive compositions, but also coating compositions, cosmetic compositions, ink compositions, inkjet ink compositions, and ink compositions used in three-dimensional modeling.

[0015] In the general formula [1], R 2 , R 3In the general formula [1], the number of carbon atoms in the chain hydrocarbon group or cyclic hydrocarbon group is preferably 8 or more, more preferably 12 or more, and even more preferably 16 or more, from the viewpoint of improving the wettability of the polymerizable composition according to this embodiment to a low-polarity substrate. On the other hand, the number of carbon atoms in the chain hydrocarbon group or cyclic hydrocarbon group is not particularly limited, but in order to sufficiently maintain the wettability of the polymerizable composition to a high-polarity substrate, that is, from the viewpoint of the balance of wettability to a low-polarity substrate and a high-polarity substrate, it is usually 36 or less, preferably 24 or less, and more preferably 22 or less. 2 and R 3 The number of members of the saturated ring containing a nitrogen atom carrying the group is preferably 6 or more and 12 or less, from the viewpoint of balancing the wettability of the polymerizable composition to low-polarity substrates and high-polarity substrates.

[0016] The N-substituted (meth)acrylamide (A) used in this embodiment is an N-monosubstituted (meth)acrylamide or an N,N-disubstituted (meth)acrylamide. As described above, the N-substituted (meth)acrylamide (A) preferably has one or more structures selected from linear saturated and unsaturated structures and cyclic saturated and unsaturated structures having 6 to 36 carbon atoms as a substituent. Furthermore, it is more preferable that the N-substituted (meth)acrylamide (A) has at least one substituent with an unsaturated structure. Generally, among aliphatic compounds with the same number of carbon atoms, those containing unsaturated bonds in their structures tend to have lower melting points than those without. As will be described later, if the N-substituted (meth)acrylamide (A) is liquid at room temperature, its content in the polymerizable composition of this embodiment can be adjusted to some extent. Therefore, it is more preferable that the N-substituted (meth)acrylamide (A) contains one or more substituents with an unsaturated structure, which has the effect of lowering its melting point.

[0017] The polymerizable composition according to this embodiment preferably has a saturated water absorption of 10% or less at room temperature. In this specification, room temperature refers to 5°C to 35°C under atmospheric pressure. The saturated water absorption of the cured product is the water absorption in a saturated water absorption state, and can be calculated by the method described below. The saturated water absorption state is sufficient, and the method and conditions for achieving this state are not limited. If the saturated water absorption of the cured product is 10% or less, the cured product will have sufficient water resistance. The lower the saturated water absorption, the higher the water resistance of the cured product. Therefore, the saturated water absorption of the cured product is more preferably 7% or less, and particularly preferably 5% or less.

[0018] The surface tension of N-substituted (meth)acrylamide (A) is 24.0 to 46.0 mN m -1 In this specification, the surface tension of the N-substituted (meth)acrylamide (A) is a calculated value at 23°C obtained by the Meissner method (Chemical Engineering Handbook, 7th revised edition, p. 66), with an average error of 3%.

[0019] When the surface tension of the N-substituted (meth)acrylamide (A) is within the above range, when a polymerizable composition containing the N-substituted (meth)acrylamide (A) is applied to a substrate of a different polarity, the molecules can be arranged to match the polarity of the substrate. As a result, the polymerizable composition exhibits good wettability to various substrates exhibiting a wide range of polarities as described above, and the adhesion of pressure-sensitive adhesive compositions and adhesive compositions, which are molded articles of the polymerizable composition and / or its polymer, is also improved. From these viewpoints, the surface tension of the N-substituted (meth)acrylamide (A) is 28.0 to 36.0 mN·m -1 More preferably, it is 30.0 to 33.0 mN m -1 It is particularly preferred that:

[0020] The N-substituted (meth)acrylamide (A) is preferably in a liquid state at room temperature. When the N-substituted (meth)acrylamide (A) is in a liquid state at room temperature, the content thereof in the polymerizable composition according to the present embodiment can be adjusted to some extent as desired without the need for heating or other operations, and the transparency of the resulting polymerizable composition can be easily maintained. The N-substituted (meth)acrylamide (A) is more preferably in a liquid state at 30°C or lower, and even more preferably in a liquid state at 25°C or lower. In this specification, the term "liquid" includes both a liquid state having fluidity and a wax state having no fluidity.

[0021] In the polymerizable composition according to this embodiment, the content of the N-substituted (meth)acrylamide (A) is 1 wt% or more, and may be 100 wt%, based on the total weight of the polymerizable composition. The content of A can be appropriately adjusted depending on the specific application of the polymerizable composition. When the polymerizable composition contains 1 wt% of the N-substituted (meth)acrylamide (A), the polymerizable composition can exhibit improved curability and polymerizability against actinic energy rays and / or heat, transparency, and wettability to various substrates exhibiting a wide range of polarity. Furthermore, to exhibit a better balance between the curability, polymerizability, transparency, and wettability, the content of the N-substituted (meth)acrylamide (A) is more preferably 5 to 90 wt%, even more preferably 10 to 80 wt%, and particularly preferably 20 to 70 wt%.

[0022] When the N-substituted (meth)acrylamide (A) has an aliphatic hydrocarbon group having 6 or more carbon atoms and no unsaturated bond as a substituent, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Examples of N-substituted (meth)acrylamides include the following: n-hexyl(meth)acrylamide, sec-hexyl(meth)acrylamide, tert-hexyl(meth)acrylamide, n-heptyl(meth)acrylamide, sec-heptyl(meth)acrylamide, tert-heptyl(meth)acrylamide, n-octyl(meth)acrylamide, sec-octyl(meth)acrylamide, tert-octyl(meth)acrylamide, 2-ethylhex ... N,N-di-(2-ethylhexyl)acrylamide, n-nonyl(meth)acrylamide, n-decyl(meth)acrylamide, n-undecyl(meth)acrylamide, n-dodecyl(meth)acrylamide, n-tridecyl(meth)acrylamide, n-trimethyldecyl(meth)acrylamide, n-tetradecyl(meth)acrylamide, n-hexadecyl(meth)acrylamide, stearyl(meth)acrylamide, n-eicosyl(meth)acrylamide, n-docosyl N-cyclohexyl(meth)acrylamide, N-tetracosyl(meth)acrylamide, N-cyclohexyl(meth)acrylamide, N,N-dicyclohexyl(meth)acrylamide, N-cyclohexyl-N-methyl(meth)acrylamide, N-cyclohexyl-N-ethyl(meth)acrylamide, N-cyclohexyl-N-propyl(meth)acrylamide, N-cyclohexyl-N-butyl(meth)acrylamide, N-cyclohexyl-N-pentyl(meth)acrylamide, N-cyclohexyl N-hexyl(meth)acrylamide, N-phenyl(meth)acrylamide, N-(meth)acryloylpiperidine, N-(meth)acryloyl-2-methylpiperidine, N-(meth)acryloyl-3-methylpiperidine, N-(meth)acryloyl-4-methylpiperidine, N-(meth)acryloyl-2,6-dimethylpiperidine, N-(meth)acryloyl-3,5-dimethylpiperidine, N-(meth)acryloyl-3,3-dimethylpiperidine, N-(meth)acryloyl-4,4-Dimethylpiperidine, N-(meth)acryloyl-2,2,6,6-tetramethylpiperidine, N-(meth)acryloyl-2-methyl-5-ethylpiperidine, N-(meth)acryloyl-4-methyl-4-ethylpiperidine, N-(meth)acryloyl-2-ethylpiperidine, N-(meth)acryloyl-3-ethylpiperidine, N-(meth)acryloyl-4-ethylpiperidine, N-(meth)acryloyl-2-propylpiperidine acryloyl hexamethyleneimine, N-(meth)acryloyl-2-methylhexamethyleneimine, N-(meth)acryloyl-3-methylhexamethyleneimine, N-(meth)acryloyl ... -4-methylhexamethyleneimine, N-(meth)acryloyl-2-ethylhexamethyleneimine, N-(meth)acryloyl-3-ethylhexamethyleneimine, N-(meth)acryloyl-4-ethylhexamethyleneimine, N-(meth)acryloyl-3-propylhexamethyleneimine, N-(meth)acryloyl-4-propylhexamethyleneimine, N-(meth)acryloyl-3-isopropylhexamethyleneimine, N-( N-(meth)acryloyl-4-isopropylhexamethyleneimine, N-(meth)acryloyl-3,5-dimethylhexamethyleneimine, N-(meth)acryloyl-4,4-dimethylhexamethyleneimine, N-(meth)acryloylheptamethyleneimine, N-(meth)acryloyloctamethyleneimine, N-(meth)acryloyldecamethyleneimine, dopamine(meth)acrylamide, 3-(meth)acrylamidophenylboronic acid. Among these, from the viewpoint of easy availability of industrial products, n-hexyl(meth)acrylamide, n-octyl(meth)acrylamide, tert-octyl(meth)acrylamide, 2-ethylhexyl(meth)acrylamide, N,N-Di-(2-ethylhexyl)acrylamide, n-Nonyl(meth)acrylamide, n-Decyl(meth)acrylamide, n-Dodecyl(meth)acrylamide, n-Tridecyl(meth)acrylamide, n-Trimethyldecyl(meth)acrylamide, n-Tetradecyl(meth)acrylamide, n-Hexadecyl(meth)acrylamide, Stearyl(meth)acrylamide, N-Cyclohexyl(meth)acrylamide, N,N-Dicyclohexyl(meth)acrylamide Preferred are N-cyclohexyl-N-methyl(meth)acrylamide, N-(meth)acryloylpiperidine, N-(meth)acryloyl-2-methylpiperidine, N-(meth)acryloyl-4-methylpiperidine, N-(meth)acryloyl-2,6-dimethylpiperidine, N-(meth)acryloyl-3,5-dimethylpiperidine, N-phenyl(meth)acrylamide, dopamine(meth)acrylamide, and 3-(meth)acrylamidophenylboronic acid.

[0023] When the N-substituted (meth)acrylamide (A) has an aliphatic hydrocarbon group having 6 or more carbon atoms and containing an unsaturated bond as a substituent, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Examples of N-substituted (meth)acrylamides include the following: hexenyl(meth)acrylamide, heptenyl(meth)acrylamide, octenyl(meth)acrylamide, nonenyl(meth)acrylamide, decenyl(meth)acrylamide, undecenyl(meth)acrylamide, dodecenyl(meth)acrylamide, tetradecenyl(meth)acrylamide, hexadecenyl(meth)acrylamide, oleyl(meth)acrylamide, icosenyl(meth)acrylamide, docosenyl(meth)acrylamide, tetracosenyl(meth)acrylamide, octadecadienyl(meth)acrylamide, icosadienyl(meth)acrylamide, docosadienyl(meth)acrylamide, tetracosane(meth)acrylamide, octadecadienyl(meth)acrylamide, icosane(meth)acrylamide, docosane ... octadecadienyl(meth)acrylamide, octadecadienyl(meth)acrylamide, octadecadienyl(meth)acrylamide, octadecadienyl(meth)acrylamide, octadecadienyl(meth)acrylamide, octadecadienyl(meth)acrylamide, oc Dienyl(meth)acrylamide, octadecatrienyl(meth)acrylamide, icosatrienyl(meth)acrylamide, docosatrienyl(meth)acrylamide, tetracosatrienyl(meth)acrylamide, octadecatetraenyl(meth)acrylamide, icosatetraenyl(meth)acrylamide, docosatetraenyl(meth)acrylamide, tetracosatetraenyl(meth)acrylamide, octadecapentaenyl(meth)acrylamide, icosapentaenyl(meth)acrylamide, docosapentaenyl(meth)acrylamide, tetracosapentaenyl(meth)acrylamide, docosahexaenyl(meth)acrylamide, tetracosahexaenyl(meth)acrylamide. Among these, octenyl(meth)acrylamide, nonenyl(meth)acrylamide, undecenyl(meth)acrylamide, and oleyl(meth)acrylamide are preferred from the viewpoint of easy availability of industrial products, etc.

[0024] In addition to the N-substituted (meth)acrylamide (A), the polymerizable composition according to this embodiment may further contain one or more compounds selected from the group consisting of a polymerization initiator, a compound having an unsaturated bond (excluding the N-substituted (meth)acrylamide (A) and polymers thereof), a non-polymerizable oligomer and a non-polymerizable polymer (excluding polymers using the N-substituted (meth)acrylamide (A)), and polymers of the polymerizable composition. When the polymerizable composition further contains a polymerization initiator, the curability and polymerizability with respect to actinic radiation and / or heat are further improved. When the polymerizable composition further contains a compound having an unsaturated bond, the composition can be more suitably used as a pressure-sensitive adhesive composition, an adhesive composition, a coating composition, and various ink compositions. Furthermore, when the polymerizable composition further contains a non-polymerizable oligomer and / or a non-polymerizable polymer, the viscosity of the polymerizable composition and the flexibility of the cured product thereof can be easily adjusted. In particular, when the polymerizable composition further contains the polymer, the adhesive strength of the pressure-sensitive adhesive composition, which is a molded product of the polymerizable composition or the polymer, to various substrates and the adhesive strength of the adhesive composition to various substrates are improved. Hereinafter, the polymerizable composition refers to both a polymerizable composition that does not contain the polymer and a polymerizable composition that contains the polymer.

[0025] Examples of the compound having an unsaturated bond include a monofunctional monomer or oligomer having one unsaturated bond, a polyfunctional monomer or oligomer having two or more unsaturated bonds, and a polymerizable polymer having an unsaturated bond. The compound having an unsaturated bond is not limited to a specific application of the polymerizable composition. The monofunctional monomer is used to adjust the viscosity of the polymerizable composition to a low viscosity, the polymerizable polymer is used to adjust the viscosity of the polymerizable composition to a high viscosity, and the polyfunctional monomer, polyfunctional oligomer, and polymerizable polymer are used to adjust the curability of the polymerizable composition or the crosslinking rate of the resulting cured product. The components other than the N-substituted (meth)acrylamide (A) in the polymerizable composition of this embodiment may be added alone or in combination of two or more. The content of each component may be adjusted appropriately depending on the specific application, but it is preferable that the monofunctional monomer be 1 to 99 wt%, the polyfunctional monomer be 0.05 to 50 wt%, the polyfunctional oligomer be 0.05 to 50 wt%, the polymerizable or non-polymerizable polymer be 0.01 to 10 wt%, and the polymer of the polymerizable composition be 0.01 to 10 wt%, based on the total weight of the polymerizable composition. In this specification, homopolymers or copolymers of various monomers with a weight-average molecular weight (Mw) of 1,000 or more but less than 10,000 are classified as oligomers, and those with an Mw of 10,000 or more are classified as polymers.

[0026] The polyfunctional monomer is a monomer having two or more unsaturated bonds selected from (meth)acrylate groups, (meth)acrylamide groups, vinyl groups, allyl groups, and maleimide groups in the molecule, and examples thereof include polyfunctional (meth)acrylates and polyfunctional (meth)acrylamides. Generally, polyfunctional monomers having 10 or less unsaturated bonds in the molecule are preferably used.

[0027] Examples of polyfunctional (meth)acrylates include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, ditetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, and polypropylene glycol di(meth)acrylate. acrylate, polytetramethylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,6-hexanediol ethylene oxide modified di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-Nonanediol di(meth)acrylate, hydroxypivalic acid neopentyl glycol di(meth)acrylate, dicyclopentanyl di(meth)acrylate, caprolactone-modified dicyclopentenyl di(meth)acrylate, ethylene oxide-modified phosphate di(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipenta Erythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol tetra(meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate, phthalic acid diglycidyl ester di(meth)acrylate, glycerin polyglycidyl ether poly(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, tricyclodecane dimethicone Methanol di(meth)acrylate, ethylene oxide modified bisphenol A di(meth)acrylate, propylene oxide modified bisphenol A di(meth)acrylate, cyclohexanedimethanol di(meth)acrylate, acrylate ester (dioxane glycol diacrylate), alkoxylated hexanediol di(meth)acrylate, alkoxylated cyclohexanedimethanol di(meth)acrylate, epoxy (meth)acrylate, urethane (meth)acrylate, isocyanuric acid ethylene oxide modified di acrylate, isocyanuric acid ethylene oxide modified tri(meth)acrylate, tri(meth)acryloyloxyethoxytrimethylolpropane, 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, etc.

[0028] Examples of polyfunctional (meth)acrylamides include methylene bis(meth)acrylamide, ethylene bis(meth)acrylamide, diallyl (meth)acrylamide, N-[tris(3-(meth)acrylamidopropoxymethyl)methyl](meth)acrylamide, N,N-bis(2-(meth)acrylamidoethyl)(meth)acrylamide, 4,7,10-trioxa-1,13-tridecane bis(meth)acrylamide, and N,N'-1,2-ethanedyl bis[N-(2-(meth)acrylamidoethyl)](meth)acrylamide. These polyfunctional monomers may be used alone or in combination of two or more.

[0029] Examples of the monofunctional monomer include radical polymerizable compounds having a reactive double bond in the molecule, such as monofunctional (meth)acrylate, monofunctional (meth)acrylamide, styrene, alkoxy group-containing monomer, vinyl group-containing monomer, allyl group-containing monomer, and maleimide group-containing monomer.

[0030] Examples of the monofunctional (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, hydroxyethyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and isopropyl (meth)acrylate. Stearyl (meth)acrylate, tridecyl (meth)acrylate, methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, propoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, methoxydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, phenoxyethyl (meth) Acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, cyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, bornyl (meth)acrylate, isobornyl (meth)acrylate, tetrahydrofurfuryl acrylate, 2-methyl-2-adamantyl (meth)acrylate, allyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, hydroxyhexyl (meth)acrylate, and the like.

[0031] Examples of monofunctional (meth)acrylamides include N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-butyl(meth)acrylamide, N-methoxymethyl(meth)acrylamide, N-ethoxymethyl(meth)acrylamide, N-methoxyethyl(meth)acrylamide, N-ethoxyethyl(meth)acrylamide, Nn-butoxymethyl(meth)acrylamide, N-isobutoxymethyl(meth)acrylamide, N-(2-hydroxyethyl)acrylamide, N-[3-(dimethylamino)]propylacrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, diacetone(meth)acrylamide, etc. These monofunctional (meth)acrylamides are included in the above-mentioned N-substituted (meth)acrylamide (B).

[0032] Examples of vinyl group-containing monomers include N-vinylpyrrolidone, N-vinylcaprolactam, acrylonitrile, vinyl acetate, styrene, vinyloxazoline, etc. These monofunctional monomers may be used alone or in combination of two or more.

[0033] Examples of monofunctional oligomers, polyfunctional oligomers, and polymerizable polymers include linear and / or branched oligomers and polymers having an acrylic, ester, ether, urethane, amide, or other skeleton, and are classified into urethane, epoxy, and acrylic types based on the main chain structure. When these are classified by weight-average molecular weight (Mw), oligomers made of the above-mentioned polyfunctional (meth)acrylates and / or polyfunctional (meth)acrylamides can be exemplified as those having an Mw of 1,000 or more but less than 10,000, and the following polymerizable polymers can be exemplified as those having an Mw of 10,000 or more: bifunctional polyurethane (meth)acrylates, polyfunctional polyurethane (meth)acrylates, bifunctional polyester (meth)acrylates, polyfunctional urethane (meth)acrylates, bifunctional polyester (meth)acrylates, polyfunctional polyester (meth)acrylates, bifunctional polyether (meth)acrylates, polyfunctional polyether (meth)acrylates, bifunctional polyamide (meth)acrylates, and polyfunctional poly (meth)acrylates. Amide (meth)acrylate, bifunctional poly(meth)acrylic acid ester (meth)acrylate, multifunctional poly(meth)acrylic acid ester (meth)acrylate, bifunctional poly(meth)acrylic acid ester (meth)acrylamide, multifunctional poly(meth)acrylic acid ester (meth)acrylamide, bifunctional poly(meth)acrylamide (meth)acrylate, multifunctional poly(meth)acrylamide (meth)acrylate, bifunctional polystyrene (meth)acrylate, multifunctional polystyrene (meth)acrylate, bifunctional polyacrylonitrile (meth)acrylate, multifunctional polyacrylonitrile (meth)acrylate, bifunctional epoxy acrylate (bisphenol A type), multifunctional epoxy acrylate (bisphenol A type), etc. These oligomers or polymers may be used alone or in combination of two or more.

[0034] Furthermore, from the viewpoint of easy availability as a commercially available product, the monofunctional or polyfunctional oligomer may be, for example, a urethane acrylate manufactured by Mitsubishi Chemical Corporation under the trade names UV-3200B, UV-3000B, UV-6640B, UV-3700B, UV-3310B, or UV-7000B; a product manufactured by Shin-Nakamura Chemical Co., Ltd. under the trade names U-4HA and U-200PA; a product manufactured by Daicel-Cytec under the trade names EBECRYL245 and EBEC Examples of suitable curable urethane oligomers include RYL1259, EBECRYL8210, EBECRYL284, EBECRYL8402, products manufactured by SARTOMER under the trade names CN944, CN969, CN9002, and CN9029, products manufactured by Negami Chemical Industrial Co., Ltd. under the trade names UN1255 and UN-5507, and products manufactured by Kyoeisha under the trade names AH-600 and UA-306I. Examples of suitable curable urethane oligomers include Quick Cure (registered trademark) 6100, Quick Cure (registered trademark) 7100, and Quick Cure (registered trademark) 8100 manufactured by KJ Chemicals.

[0035] The compound having an unsaturated bond may be a monomer or oligomer having an unsaturated bond, and is preferably the various monofunctional monomers and polyfunctional monomers and oligomers described above. From the viewpoint of obtaining a thermoplastic polymer used to adjust physical properties such as viscosity, the compound having an unsaturated bond contained in the polymerizable composition of this embodiment is preferably a monofunctional monomer having one unsaturated bond, and from the viewpoint of increasing the cohesive strength of the resulting polymer, a monomer capable of introducing a crosslinking point is particularly preferred. The content of these compounds having an unsaturated bond may be adjusted as desired depending on the specific application, but is preferably 1 to 99 wt % in total relative to the total weight of the polymerizable composition of this embodiment.

[0036] The monomer capable of introducing the crosslinking point is a monomer having one or more reactive functional groups in the molecule, and examples thereof include functional group-containing (meth)acrylic monomers such as hydroxyl group-containing (meth)acrylic monomers, carboxyl group-containing (meth)acrylic monomers, amino group-containing (meth)acrylic monomers, acetoacetyl group-containing (meth)acrylic monomers, isocyanate group-containing (meth)acrylic monomers, glycidyl group-containing (meth)acrylic monomers, and oxazoline group-containing vinyl monomers.

[0037] Examples of the hydroxyl group-containing (meth)acrylic monomer include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, and 8-hydroxyoctyl (meth)acrylate; hydroxyalkyl (meth)acrylamides such as N-hydroxyethyl (meth)acrylamide and N-hydroxypropyl (meth)acrylamide; and 2-acryloyloxyethyl 2-hydroxyethyl Examples of the monomers include primary hydroxyl group-containing (meth)acrylic monomers such as phthalic acid and N-methylol (meth)acrylamide, secondary hydroxyl group-containing (meth)acrylic monomers such as 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate and 2-hydroxy-3-phenoxypropyl (meth)acrylate, and tertiary hydroxyl group-containing (meth)acrylic monomers such as 2,2-dimethyl-2-hydroxyethyl (meth)acrylate. Among these, hydroxyalkyl (meth)acrylates are preferably used.

[0038] Examples of the carboxyl group-containing (meth)acrylic monomer include monocarboxylic acids such as (meth)acrylic acid and crotonic acid, and dicarboxylic acids such as maleic acid, maleic anhydride, fumaric acid, citraconic acid, and itaconic acid. Among these, (meth)acrylic acid is preferably used.

[0039] Examples of the amino group-containing (meth)acrylic monomer include aminoalkyl (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, N,N-di-t-butylaminoethyl (meth)acrylate, and N,N-diethylaminoethyl (meth)acrylate; and aminoalkyl (meth)acrylamides such as N,N-dimethylaminoethyl (meth)acrylamide, N,N-diethylaminoethyl (meth)acrylamide, and N,N-dimethylaminopropyl (meth)acrylamide.

[0040] Examples of the acetoacetyl group-containing (meth)acrylic monomer include 2-(acetoacetoxy)ethyl (meth)acrylate.

[0041] Examples of the glycidyl group-containing (meth)acrylic monomer include glycidyl (meth)acrylate, (meth)acrylamide glycidyl, N-hydroxyethyl (meth)acrylamide glycidyl ether, N-methyl-N-hydroxyethyl (meth)acrylamide glycidyl ether, N-ethyl-N-hydroxyethyl (meth)acrylamide glycidyl ether, N-propyl-N-hydroxyethyl (meth)acrylamide glycidyl ether, N-butyl-N-hydroxyethyl (meth)acrylamide glycidyl ether, N-hydroxypropyl (meth)acrylamide glycidyl ether, N-hydroxybutyl (meth)acrylamide glycidyl ether, N-hydroxypentyl (meth)acrylamide glycidyl ether, N-hydroxyhexyl (meth)acrylamide glycidyl ether, N-hydroxyheptyl (meth)acrylamide glycidyl ether, and N-hydroxyoctyl (meth)acrylamide glycidyl ether.

[0042] Examples of the oxazoline group-containing vinyl monomer include 2-vinyl-2-oxazoline, 4-methyl-2-vinyl-2-oxazoline, 5-methyl-2-vinyl-2-oxazoline, 4-ethyl-2-vinyl-2-oxazoline, 5-ethyl-2-vinyl-2-oxazoline, 4,4-dimethyl-2-vinyl-2-oxazoline, 4,4-diethyl-2-vinyl-2-oxazoline, 4,5-dimethyl-2-vinyl-2-oxazoline, 4,5-diethyl-2-vinyl-2-oxazoline, 2-isopropenyl Examples of suitable crosslinking monomers include 2-vinyl-2-oxazoline, 4-methyl-2-isopropenyl-2-oxazoline, 5-methyl-2-isopropenyl-2-oxazoline, 4-ethyl-2-isopropenyl-2-oxazoline, 5-ethyl-2-isopropenyl-2-oxazoline, 4,4-dimethyl-2-isopropenyl-2-oxazoline, 4,4-diethyl-2-isopropenyl-2-oxazoline, 4,5-dimethyl-2-isopropenyl-2-oxazoline, and 4,5-diethyl-2-isopropenyl-2-oxazoline. Highly reactive 2-vinyl-2-oxazoline, 5-methyl-2-vinyl-2-oxazoline, and 4,4-dimethyl-2-vinyl-2-oxazoline are preferred, with 2-vinyl-2-oxazoline being most preferred. The monomers capable of introducing these crosslinking points are not limited to a single type, and multiple types may be used in combination.

[0043] In this embodiment, the crosslinking agent is a compound capable of introducing a crosslinked structure into a cured product of the polymerizable composition, and examples thereof include the above-mentioned monomers capable of introducing crosslinking points, oligomers and polymers obtained by polymerizing the monomers capable of introducing multiple crosslinking points, compounds having two or more reactive functional groups in the molecule, the above-mentioned polyfunctional monomers having two or more unsaturated bonds in the molecule, polyfunctional oligomers and polymerizable polymers. Note that in this embodiment, when the monomer capable of introducing a crosslinking point is a monofunctional monomer having one or more reactive functionalities in the molecule, it is treated as a monofunctional monomer. In this embodiment, crosslinking methods using a crosslinking agent include: (1) a method in which a polymerizable composition or a polymer thereof further contains a compound having a functional group (e.g., an isocyanate group or a carboxyl group) that reacts with a reactive functional group (e.g., a hydroxyl group or an amino group) contained in the polymerizable composition or the polymer thereof, thereby crosslinking the polymer; (2) a method in which a polymerizable composition or a polymer thereof contains a polyfunctional monomer, a polyfunctional oligomer, or a polymerizable polymer, thereby crosslinking the polymer; and (3) a method in which a crosslinking agent such as a polyfunctional monomer, a polyfunctional oligomer, a polymerizable polymer, or a monomer that can introduce crosslinking points is contained in the polymerizable composition or the polymer thereof, thereby crosslinking the polymer; and (4) a method in which a crosslinking agent such as a polyfunctional monomer, a polyfunctional oligomer, a polymerizable polymer, or a monomer that can introduce crosslinking points is contained in the polymerizable composition or the polymer thereof, thereby crosslinking the polymer; and (5) a method in which a crosslinking agent is contained in the polymerizable composition or the polymer thereof, such as a polyfunctional monomer, a polyfunctional oligomer, a polymerizable polymer, or a monomer that can introduce crosslinking points, thereby crosslinking the polymer; and (6) a method in which the crosslinking method (3) is a combination of the crosslinking methods (1) and (2).

[0044] In the above-mentioned crosslinking method (1), examples of the crosslinking agent (i.e., a compound having a functional group that reacts with a reactive functional group contained in the polymerizable composition or its polymer) include an isocyanate compound, an epoxy compound, an aziridine compound, a compound having a carboxyl group, an oxazoline group, and the like.

[0045] Examples of the isocyanate compound include aromatic isocyanates such as tolylene diisocyanate and xylene diisocyanate, alicyclic isocyanates such as isophorone diisocyanate, and aliphatic isocyanates such as hexamethylene diisocyanate. More specifically, examples of the isocyanate compound include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate; alicyclic isocyanates such as cyclopentylene diisocyanate, cyclohexylene diisocyanate and isophorone diisocyanate; aromatic diisocyanates such as 2,4-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate and xylylene diisocyanate; and isocyanate adducts such as trimethylolpropane / tolylene diisocyanate trimer adduct (manufactured by Tosoh Corporation, trade name: Coronate L), trimethylolpropane / hexamethylene diisocyanate trimer adduct (manufactured by Tosoh Corporation, trade name: Coronate HL), and isocyanurate of hexamethylene diisocyanate (manufactured by Tosoh Corporation, trade name: Coronate HX). These isocyanate compounds may be used alone or in combination of two or more.

[0046] Examples of epoxy compounds include polyethylene glycol diglycidyl ether, polyglycerol polyglycidyl ether, glycerin diglycidyl ether, diglycidyl ether, trimethylolpropane triglycidyl ether, diglycidylaniline, N,N,N',N'-tetraglycidyl-m-xylylenediamine (manufactured by Mitsubishi Gas Chemical Company, Inc., trade name: TETRAD-X), and 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane (manufactured by Mitsubishi Gas Chemical Company, Inc., trade name: TETRAD-C). These compounds may be used alone or in combination of two or more.

[0047] Examples of the aziridine compound include commercially available products under the trade names HDU, TAZM, and TAZO (all manufactured by Sogo Pharmaceutical Co., Ltd.) These compounds may be used alone or in combination of two or more.

[0048] Examples of the compound having a carboxyl group include aromatic dicarboxylic acids such as phthalic acid, isophthalic acid, 1,4-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, diphenyldicarboxylic acid, diphenoxyethanedicarboxylic acid, diphenyletherdicarboxylic acid, and diphenylsulfonedicarboxylic acid; alicyclic dicarboxylic acids such as 1,3-cyclopentanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, and 1,4-cyclohexanedicarboxylic acid; aliphatic dicarboxylic acids such as malonic acid, dimethylmalonic acid, succinic acid, 3,3-diethylsuccinic acid, glutaric acid, 2,2-dimethylglutaric acid, adipic acid, 2-methyladipic acid, trimethyladipic acid, pimelic acid, azelaic acid, sebacic acid, and suberic acid; and compounds having a dicarboxyl group derived from hydroxycarboxyl groups such as glycolic acid, 3-hydroxybutyric acid, 4-hydroxyvaleric acid, hydroxypropionic acid, hydroxycaproic acid, and hydroxybenzoic acid, as well as ester-forming derivatives thereof or anhydrides thereof. These compounds may be used alone or in combination of two or more.

[0049] Examples of compounds having an oxazoline group include alkylene bisoxazolines such as tetramethylene bisoxazoline and hexamethylene bisoxazoline, aromatic bisoxazolines such as 1,3-phenylene bis(2-oxazoline) and 1,4-bis(4,5-dihydro-2-oxazolyl)benzene, and compounds having an oxazoline group, such as homopolymers of the various oxazoline group-containing vinyl monomers mentioned above or copolymers with compounds having unsaturated bonds. These compounds may be used alone or in combination of two or more.

[0050] The content of the crosslinking agent (i.e., a compound having two or more functional groups in its molecule that react with reactive functional groups contained in the polymerizable composition or its polymer) in crosslinking method (1) can be appropriately selected based on the balance between the amount and molecular weight of the reactive functional groups contained in the polymerizable composition or its polymer, as well as the specific application. Typically, the content is preferably 0.1 to 15 wt %, more preferably 0.5 to 10 wt %, and particularly preferably 1 to 5 wt %, based on the total weight of the polymerizable composition. If the content is less than 0.1 wt %, crosslinking by the crosslinking agent is insufficient. If the molded product after the crosslinking reaction is a cured product of a pressure-sensitive adhesive composition and an adhesive composition, it may not exhibit sufficient durability and may tend to cause adhesive residue (contamination) in the pressure-sensitive adhesive composition. Furthermore, if the molded product after the crosslinking reaction is a cured product of a coating agent, it may not exhibit sufficient surface hardness. If the molded product after the crosslinking reaction is a cured product of a three-dimensional modeling ink, i.e., a three-dimensional modeling object, it may not be possible to obtain a model with sufficient hardness and tensile strength. On the other hand, if the content exceeds 15 wt%, when the molded article after the crosslinking reaction is a cured product of the pressure-sensitive adhesive composition and the adhesive composition, the flexibility decreases, and the adhesion to the substrate also decreases, making it impossible to obtain sufficient adhesive strength and bond strength. Furthermore, when the molded article after the crosslinking reaction is a cured product of the ink for three-dimensional modeling, i.e., a three-dimensional model, it may not be possible to obtain a model with sufficient breaking elongation. Note that the crosslinking reaction in crosslinking method (1) may be carried out at room temperature, but is preferably carried out at a temperature of about 40°C to 120°C to promote the reaction.

[0051] In the crosslinking method (2), the crosslinking agent (i.e., polyfunctional monomer, polyfunctional oligomer, or polymerizable polymer) can be any of those described above. Furthermore, in the crosslinking method (2), various types of active energy rays, which will be described later, can be used for irradiation. When ultraviolet rays (UV, UV-LED, etc.) or visible light are used as the active energy rays, it is preferable to use a photopolymerization initiator in combination. When electron beams (EB) or energy rays with wavelengths shorter than electron beams are used as the active energy rays, high energy can be imparted, so a photopolymerization initiator does not need to be contained. Furthermore, when the unsaturated bond in the molecule of the polyfunctional monomer, polyfunctional oligomer, or polymerizable polymer is a self-initiating functional group such as a maleimide group, an allyl ether group, or a vinyl ether group, a photopolymerization initiator does not need to be contained.

[0052] The content of the crosslinking agent (i.e., polyfunctional monomer, polyfunctional oligomer, or polymerizable polymer) in crosslinking method (2) is preferably 0.05 to 50 wt % relative to the total weight of the polymerizable composition. From the viewpoint of achieving a good balance between the adhesion of the cured product to various substrates after crosslinking and the hardness and strength of the resulting cured product, 0.1 to 30 wt % is more preferable, and 0.5 to 20 wt % is particularly preferable. If the content is less than 0.05 wt %, crosslinking by the crosslinking agent is insufficient. If the molded product after the crosslinking reaction is a pressure-sensitive adhesive composition, sufficient durability may not be obtained, and the pressure-sensitive adhesive composition may tend to be left with adhesive residue (contamination). Furthermore, if the molded product after the crosslinking reaction is a cured product of a coating agent, sufficient surface hardness may not be obtained. If the molded product after the crosslinking reaction is a cured product of an ink for a three-dimensional modeling material, i.e., a three-dimensional object, the molded object may not have sufficient hardness and tensile strength. On the other hand, if the content exceeds 50% by weight, when the molded article after the crosslinking reaction is a cured product of a pressure-sensitive adhesive composition and an adhesive composition, shrinkage due to curing specific to active energy ray curing is likely to occur, which tends to cause peeling or cracking. In that case, of course, sufficient adhesive strength and bonding strength cannot be obtained. Furthermore, when the molded article after the crosslinking reaction is a cured product of a coating agent, peeling or cracking of the cured film of the molded article is likely to occur due to curing shrinkage. When the molded article after the crosslinking reaction is a three-dimensional object, sufficient breaking elongation may not be obtained.

[0053] The content of the crosslinking agent (i.e., polyfunctional monomer, polyfunctional oligomer, or polymerizable polymer, and compound having two or more reactive functional groups in the molecule) in the crosslinking method (3) varies depending on the type of crosslinking agent used. The content of the polyfunctional monomer, polyfunctional oligomer, or polymerizable polymer is preferably 0.05 to 30 wt % based on the total weight of the polymerizable composition, and the content of the compound having two or more reactive functional groups in the molecule is preferably 0.1 to 10 wt % based on the total weight of the polymerizable composition. Furthermore, since the polyfunctional monomer, polyfunctional oligomer, or polymerizable polymer and the compound having two or more reactive functional groups in the molecule are used as a mixture, the total content of these crosslinking agents is preferably 0.15 to 40 wt %, more preferably 0.2 to 35 wt %, and particularly preferably 0.5 to 30 wt %, based on the total weight of the polymerizable composition. If the total content is less than 0.15 wt%, crosslinking by the crosslinking agent will be insufficient. Therefore, if the molded product after the crosslinking reaction is a cured product of the pressure-sensitive adhesive composition and the adhesive composition, it may not have sufficient durability and may tend to cause adhesive residue (contamination) in the pressure-sensitive adhesive composition. Furthermore, if the molded product after the crosslinking reaction is a cured product of a coating agent, it will not have sufficient surface hardness. If the molded product after the crosslinking reaction is a cured product of an ink for three-dimensional modeling, i.e., a three-dimensional model, it may not be possible to obtain a model with sufficient hardness and tensile strength. If the total content exceeds 40 wt%, if the molded product after the crosslinking reaction is a cured product of the pressure-sensitive adhesive composition and the adhesive composition, it will have reduced flexibility and adhesion to the substrate, resulting in insufficient adhesive strength and adhesion. Furthermore, if the molded product after the crosslinking reaction is a cured product of an ink for three-dimensional modeling, i.e., a three-dimensional model, it may not be possible to obtain a model with sufficient breaking elongation.

[0054] As described above, the polymerizable composition according to this embodiment may further contain a non-polymerizable oligomer having a weight-average molecular weight (Mw) of 1,000 or more but less than 10,000 and / or a non-polymerizable polymer having a Mw of 10,000 or more. Examples of the non-polymerizable oligomer and non-polymerizable polymer include thermoplastic resins, rosin-based resins, and mixtures thereof. Examples of the thermoplastic resin include (meth)acrylic resins, cyclic polyolefin resins, cellulose resins, polyester resins, polyurethane resins, polysulfonic acid resins, ABS resins, which are copolymers of acrylonitrile, butadiene, and styrene, polycarbonate resins, polyamide resins, and polyimide resins. Examples of rosin-based resins include natural rosins such as gum rosin, and modified rosin resins such as hydrogenated rosins obtained by modifying natural rosin, disproportionated rosin, rosin-modified phenolic resins, maleic acid-modified rosin resins, maleated rosin, and esterified gum. These non-polymerizable oligomers and non-polymerizable polymers may be used alone or in combination of two or more.

[0055] As described above, the polymerizable composition according to this embodiment may further contain a polymerization initiator and / or a compound having an unsaturated bond. In this case, the polymerizable composition has improved curability and polymerizability due to active energy rays and / or heat, and can be suitably used as an active energy ray- and / or heat-curable pressure-sensitive adhesive composition, adhesive composition, coating composition, ink composition, and the like. For example, as a pressure-sensitive adhesive composition, an adhesive layer can be formed by applying the polymerizable composition to a separator or various substrates described below and then curing it with active energy rays. In this specification, polymerization of a polymerizable composition with active energy rays and heat is also referred to as hybrid polymerization. In hybrid polymerization, polymerization may be carried out in the order of active energy rays and heat, or may be carried out in the order of heat and active energy rays.

[0056] Active energy rays are defined as energy rays capable of generating active species by decomposing a compound (photopolymerization initiator) that generates active species. Examples of such active energy rays include visible light, ultraviolet light, infrared light, α-rays, β-rays, γ-rays, X-rays, and electron beams (EB). When electron beams are used as active energy rays, a photopolymerization initiator does not need to be used. On the other hand, when ultraviolet light or visible light is used, a photopolymerization initiator is preferably used. Irradiation with active energy rays is preferably carried out in an inert gas atmosphere such as nitrogen gas or carbon dioxide gas, or in an atmosphere with a reduced oxygen concentration. However, the polymerizable composition according to this embodiment has good curability due to the presence of the N-substituted (meth)acrylamide (A), and can be sufficiently cured even in an ordinary air atmosphere. The irradiation temperature of the active energy rays is preferably 10°C to 200°C, and the irradiation time is preferably 1 second to 60 minutes.

[0057] The photopolymerization initiator may be a substance that generates radicals when irradiated with ultraviolet light of an appropriate wavelength that can trigger the polymerization reaction depending on the type of active energy ray reactive component (i.e., a photoradical polymerization initiator). The photopolymerization initiator may be appropriately selected from conventional ones such as acetophenone-based, benzoin-based, benzophenone-based, and thioxanthone-based initiators, and commercially available products include those manufactured by IGM Resins BV under the trade names Omnirad 1116, Omnirad 1173, Omnirad 184, Omnirad 369, Omnirad 500, Omnirad 651, Omnirad 754, Omnirad 819, Omnirad 907, Omnirad 1300, Omnirad 1800, Omnirad 1870, Omnirad 2959, Omnirad 4265, and Omnirad TPO, and those manufactured by UCB under the trade name Ubecryl P36. These photopolymerization initiators may be used alone or in combination of two or more.

[0058] The photoradical polymerization initiator is not particularly limited, and examples thereof include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and anisole methyl ether; acetophenones such as 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl)ketone, α-hydroxy-α,α'-dimethylacetophenone, methoxyacetophenone, 2,2'-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-cyclohexylacetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenyl ketone, 4-phenoxydichloroacetophenone, and 4-t-butyl-dichloroacetophenone; propiophenones such as 2-hydroxy-2-methylpropiophenone and 2-hydroxy-4'-isopropyl-2-methylpropiophenone; benzophenone; methylbenzyl acetophenone; Benzophenones such as benzophenone, p-chlorobenzophenone, and p-dimethylaminobenzophenone; thioxanthone, 2-chlorothioxanthone, 2-ethylthioxanthone, 2-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoylphenylphosphine oxide, and 2,4,6-trimethylbenzoylphenylphosphine oxide; Examples of the photoradical polymerization initiator include acylphosphine oxides such as bis(2,4,6-trimethylbenzoyl)-2,4-di-n-butoxyphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphenylphosphine oxide, benzil, dibenzosuberone, and α-acyloxime ester. One type of photoradical polymerization initiator may be used alone, or two or more types may be used in combination.

[0059] The content of these photopolymerization initiators is usually 0.1 to 10 wt %, preferably 0.1 to 5 wt %, and more preferably 0.5 to 3 wt %, based on the total weight of the polymerizable composition according to this embodiment. If the content of the photopolymerization initiator is less than 0.1 wt %, sufficient curing properties cannot be obtained, and if it exceeds 10 wt %, the properties such as strength of the cured product may decrease.

[0060] Thermal polymerization of the polymerizable composition according to this embodiment can be carried out by a known method in the presence of a thermal polymerization initiator, such as emulsion polymerization, solution polymerization, suspension polymerization, or bulk polymerization. When using solution polymerization, the solvent that can be used is not particularly limited as long as it dissolves the polymerized product. Examples of suitable solvents include aromatic hydrocarbons such as benzene, toluene, ethylbenzene, and xylene; aliphatic hydrocarbons such as hexane, heptane, octane, decane, and cyclohexane; esters such as ethyl acetate, butyl acetate, and 2-hydroxyethyl acetate; aliphatic alcohols such as ethyl alcohol, n-propyl alcohol, and isopropyl alcohol; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; acetonitrile; and N,N-dimethylformamide. These solvents may be used alone or in combination. Low-boiling solvents such as ethyl acetate, methyl ethyl ketone, and acetone are particularly preferred for their ease of removal during the formation of molded articles. The temperature and time of thermal polymerization vary depending on the thermal polymerization method employed and the thermal polymerization initiator used, but are usually calculated based on the half-life of the initiator. The temperature is usually preferably 60°C to 120°C, and the time is usually preferably 2 hours to 20 hours, more preferably 5 hours to 10 hours.

[0061] Examples of the thermal polymerization initiator include thermal radical polymerization initiators, such as azo compound catalysts (e.g., azobisisobutyronitrile, azobisvaleronitrile, and azobis(isobutyrate)dimethyl), peroxide catalysts (e.g., benzoyl peroxide and hydrogen peroxide), and persulfate catalysts (e.g., ammonium persulfate and sodium persulfate). The content of the thermal polymerization initiator is approximately 0.01 to 10 wt % based on the total weight of the polymerizable composition. Furthermore, conventional radical polymerization techniques, such as molecular weight adjustment using a chain transfer agent, can be applied.

[0062] As described above, a polymer obtained by polymerizing the polymerizable composition according to this embodiment using one of the various methods described above may be further contained as a component of the polymerizable composition. The molecular weight of the polymer of the polymerizable composition according to this embodiment is typically 1,000 to 2,000,000 in weight-average molecular weight (Mw), preferably 5,000 to 1,000,000, and particularly preferably 10,000 to 500,000. When the Mw is within the range of 1,000 to 2,000,000, the solution viscosity when the polymer is dissolved in a solvent or a general-purpose low-viscosity monomer is neither too high nor too low, making it easy to handle and enabling high-precision processing of pressure-sensitive adhesive sheets, coating films, three-dimensional objects, and the like. When the polymer is diluted with ethyl acetate to a solids content of 30%, the solution viscosity at 25°C is typically 10 to 100,000 mPa·s, preferably 500 to 10,000 mPa·s, and more preferably 1,000 to 5,000 mPa·s. The viscosity can be measured according to the cone-plate viscometer method of JIS K5600-2-3.

[0063] A fifth embodiment of the present invention is a pressure-sensitive adhesive composition (hereinafter also referred to as a pressure-sensitive adhesive). The pressure-sensitive adhesive composition according to the fifth embodiment contains the polymerizable composition according to any one of the first to fourth embodiments or a polymer thereof, or the polymerizable composition or a polymer thereof and a crosslinking agent. The polymerizable compositions according to any one of the first to fourth embodiments or a polymer thereof contain an N-substituted (meth)acrylamide (A), and therefore have sufficient cohesive strength and adhesive strength, adhesion to various substrates, and stain resistance, as well as durability and yellowing resistance as a pressure-sensitive adhesive composition. Therefore, the polymerizable composition or a polymer thereof can be used as a pressure-sensitive adhesive composition as is. On the other hand, a pressure-sensitive adhesive composition having even better stain resistance and durability can be obtained by crosslinking a pressure-sensitive adhesive composition containing the polymerizable composition or a polymer thereof by the crosslinking methods (1) to (3) using a crosslinking agent described above.

[0064] The pressure-sensitive adhesive composition according to the fifth embodiment can be used as an adhesive layer directly after being applied to or formed on a separator or a substrate. Alternatively, it can be cured by active energy rays and / or heat to form an adhesive layer, i.e., it can be used as an active energy ray- and / or heat-curable pressure-sensitive adhesive composition. When the pressure-sensitive adhesive composition contains an organic solvent, the composition is dried at a temperature of 60 to 120°C for 1 to 30 minutes after being applied to or formed on a separator or a substrate. The pressure-sensitive adhesive composition can be applied to a separator or a substrate by a conventionally known method, such as spin coating, spray coating, knife coating, dipping, gravure roll coating, reverse roll coating, screen printing, or bar coating.

[0065] A laminate can be obtained by laminating an adhesive layer made of the adhesive composition according to the fifth embodiment onto various substrates. Examples of methods for laminating the adhesive layer onto various substrates include a transfer method and a roll-to-roll method. The thickness of the adhesive layer in the laminate is not particularly limited because it differs depending on the intended use, but is typically 4 μm to 150 μm, and is preferably about 20 μm to 120 μm when used as an automotive component, and about 30 μm to 100 μm when used as an electronic material or optical component.

[0066] Substrates can be used in a wide range of applications, from low to high polarity, including organic substrates, inorganic substrates, and substrates made of organic-inorganic composite materials. Examples of such materials include polyolefins such as polyethylene and polypropylene, polyethylene terephthalate, polycarbonate, ABS resin (an acrylonitrile-butadiene-styrene copolymer), acrylic resins such as polyimide, polyamide, and polymethyl methacrylate, metals such as steel, stainless steel, copper, and aluminum, and glass, as well as hybrid materials in which silica particles, an inorganic material, are dispersed in polyimide, an organic material. The applications of these various substrates are not particularly limited, and examples thereof include electronic materials, optical components, and automotive components.

[0067] The adhesive layer constituting the laminate according to the fifth embodiment is formed from a polymerizable composition containing an N-substituted (meth)acrylamide (A) or a polymer thereof. The N-substituted (meth)acrylamide (A) has a hydrophobic substituent in its molecule that exhibits wettability toward low-polarity substrates and a hydrophilic (meth)acrylamide group that exhibits wettability toward high-polarity substrates, thereby imparting good adhesion to substrates ranging from low to high polarity. Furthermore, the strong cohesive force resulting from hydrogen bonding between amide groups in the A molecules provides high adhesive strength and contamination resistance. Furthermore, since the polymerizable composition or polymer exhibits high transparency and yellowing resistance, the adhesive layer obtained therefrom also exhibits high transparency and yellowing resistance, making it suitable for use in the optical field, such as adhesives for optical components and adhesive sheets. Laminates comprising an adhesive layer with these properties and various substrates can be used as adhesive films or sheets for electronic materials, optical components, and automotive components.

[0068] In the pressure-sensitive adhesive composition according to the fifth embodiment, the N-substituted (meth)acrylamide (A) contained in the pressure-sensitive adhesive composition can be brought in from a polymerizable composition containing A, and A can also be brought in as a structural unit from a polymer of the polymerizable composition and a polymer of N-substituted (meth)acrylamide (A). The total content of the N-substituted (meth)acrylamide (A) and the structural units of A in the pressure-sensitive adhesive is preferably 0.1 to 90 wt %, more preferably 1 to 70 wt %, and particularly preferably 5 to 60 wt %, based on the total weight of the pressure-sensitive adhesive composition (excluding the solvent; the same applies hereinafter). In addition, from the viewpoint of further improving the wettability and adhesion to various substrates, the surface tension of the N-substituted (meth)acrylamide (A) is preferably 24.0 to 46.0 mN·m -1 It is preferable that:

[0069] In the pressure-sensitive adhesive composition according to the fifth embodiment, from the viewpoint of improving the water resistance of the pressure-sensitive adhesive layer formed therefrom, the polymerization initiator, compound having an unsaturated bond, and non-polymerizable component (including non-polymerizable oligomer, non-polymerizable polymer, and polymer according to the second embodiment of the present invention) further contained therein are preferably hydrophobic. Furthermore, in order to adjust the balance between hydrophilicity and hydrophobicity of the pressure-sensitive adhesive composition, the content of the monofunctional monomer (excluding the N-substituted (meth)acrylamide (A)) is preferably 10 to 90 wt%, more preferably 20 to 80 wt%, and particularly preferably 30 to 70 wt%, based on the total weight of the pressure-sensitive adhesive composition. The total content of the crosslinking agent including the polyfunctional monomer is preferably 1 to 30 wt%, more preferably 2 to 20 wt%, and particularly preferably 5 to 15 wt%, based on the total weight of the pressure-sensitive adhesive composition. The total content of the non-polymerizable components is preferably 0.1 to 20 wt%, more preferably 0.5 to 15 wt%, and particularly preferably 1 to 10 wt%, based on the total weight of the pressure-sensitive adhesive composition. Such a pressure-sensitive adhesive composition has high adhesion to various substrates, and a pressure-sensitive adhesive layer formed therefrom has high adhesive strength. It is possible to obtain a pressure-sensitive adhesive composition having excellent transparency, water resistance, contamination resistance, yellowing resistance and durability, as well as laminates of a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition with various substrates.

[0070] A sixth embodiment of the present invention is an adhesive composition (hereinafter also referred to as adhesive). The adhesive composition according to the sixth embodiment contains the polymerizable composition according to any one of the first to fourth embodiments or a polymer thereof, and a crosslinking agent. By containing the N-substituted (meth)acrylamide (A) and the crosslinking agent, the adhesive composition exhibits high adhesive strength and impact resistance to various substrates having a wide range of polarities, from low polarity to high polarity, such as organic substrates, inorganic substrates, and substrates made of organic-inorganic composite materials, and can therefore be used as an adhesive composition for homogeneous or heterogeneous materials.

[0071] The term "homogeneous materials" refers to materials of the same type among the various materials mentioned above, such as resins, metals, glass, and hybrid materials. Homogeneous materials are materials with a surface tension of 22.6 mN m at 23°C. -1 ~59.0mN m -1 It is preferable that the surface tension of the same material is within the above range, and high adhesive strength can be obtained. The surface tension of each of the above materials at 23°C can be measured according to JIS K 6768, and the minimum value of the surface tension that can be measured by this method is 22.6 mN m. -1 In this specification, for the convenience of calculating the absolute value of the difference in surface tension between different materials, which will be described later, the value of the surface tension measured by this method is 22.6 mN m -1 The surface tension of the material is below 22.6 mN m -1 It is expressed as:

[0072] The term "dissimilar materials" refers to different types of materials from the various materials mentioned above, such as resins, metals, glasses, and hybrid materials. The dissimilar materials are those in which the absolute value of the difference in surface tension at 23°C between the two dissimilar materials bonded via the adhesive composition is 37.0 mN m. -1 Even if different materials are made of different materials, their surface tensions may be the same, so the absolute value of the difference in surface tension is preferably 0.0 mN m -1 As long as the absolute value of the difference in surface tension between the different materials is within the above range, good adhesion can be obtained.

[0073] In the adhesive composition according to the sixth embodiment, the N-substituted (meth)acrylamide (A) contained in the adhesive composition can be brought in from a polymerizable composition containing A, and A can also be brought in as a structural unit from a polymer of the polymerizable composition and a polymer of N-substituted (meth)acrylamide (A). The total content of the N-substituted (meth)acrylamide (A) and structural units of A in the adhesive is preferably 1 to 95 wt %, more preferably 10 to 85 wt %, and particularly preferably 2 to 80 wt %, based on the total weight of the adhesive (excluding the solvent). Furthermore, from the viewpoint of further improving the adhesive strength between homogeneous materials and between dissimilar materials, the surface tension of the N-substituted (meth)acrylamide (A) is preferably 24.0 to 46.0 mN·m -1 It is preferable that:

[0074] In the adhesive composition according to the sixth embodiment, from the viewpoint of improving the water resistance of the cured product obtained by curing the adhesive composition, it is preferable that the polymerization initiator, compound having an unsaturated bond, and non-polymerizable component (including non-polymerizable oligomer, non-polymerizable polymer, and polymer according to the second embodiment of the present invention) further contained are hydrophobic. Furthermore, in order to adjust the balance between hydrophilicity and hydrophobicity of the adhesive composition and to improve cohesive strength, the content of the monofunctional monomer (excluding N-substituted (meth)acrylamide (A)) is preferably 1 to 85 wt%, more preferably 2 to 80 wt%, and particularly preferably 5 to 75 wt%, based on the total weight of the adhesive composition. Furthermore, the content of the (meth)acrylate monomer as the monofunctional monomer is most preferably less than 50 wt%, in order to sufficiently maintain the cohesive strength derived from the (meth)acrylamide monomer.

[0075] In the adhesive composition according to the sixth embodiment, the total content of the crosslinking agent containing the polyfunctional monomer is preferably 1 to 50 wt %, more preferably 5 to 30 wt %, and particularly preferably 10 to 25 wt %, based on the total weight of the adhesive composition. If the content is less than 1 wt %, crosslinking by the crosslinking agent may be insufficient, resulting in insufficient cohesive strength of the adhesive and insufficient impact resistance and heat resistance. On the other hand, if the content exceeds 50 wt %, the crosslink density of the adhesive after crosslinking may be too high, resulting in reduced adhesion to the substrate due to shrinkage, and as a result, reduced adhesive strength. The crosslinking reaction using the crosslinking agent can be carried out by the crosslinking methods (1) to (3) described above. Furthermore, the total content of the non-polymerizable components is preferably 0.01 to 15 wt %, more preferably 0.1 to 10 wt %, and particularly preferably 0.5 to 8 wt %, based on the total weight of the adhesive composition. Such adhesive compositions have high adhesive strength, impact resistance, and water resistance to various substrates and are suitable for use in bonding homogeneous or heterogeneous materials. Furthermore, the N-substituted (meth)acrylamide (A) used in the present invention has high resistance to yellowing, and the adhesive composition according to the sixth embodiment can also be used as an adhesive for optical film laminates such as retardation films and polarizing plates.

[0076] The seventh embodiment of the present invention is a cosmetic composition (hereinafter also referred to as a cosmetic). The cosmetic composition according to the seventh embodiment contains the polymerizable composition according to the first to fourth embodiments or a polymer thereof. The cosmetic composition can be used as a cosmetic composition having moisture resistance due to the inclusion of the N-substituted (meth)acrylamide (A). Furthermore, it can also be used as a cosmetic composition having emulsion stability due to the well-balanced amphiphilicity of the N-substituted (meth)acrylamide (A). From the viewpoint of improving moisture resistance and emulsion stability, the surface tension of the N-substituted (meth)acrylamide (A) is 24.0 to 46.0 mN m -1 It is preferable that:

[0077] The cosmetic composition according to the seventh embodiment may further contain other components depending on the intended use and formulation, and the other components are not particularly limited. For example, when the cosmetic composition is used as a skin cosmetic, examples of the other components include various polymerization initiators, polyalkylene oxide macromonomers such as polyethylene oxide macromonomers, hydrocarbon oils for producing oil-in-water emulsion cosmetics, higher fatty acids, higher alcohols, synthetic ester oils, silicone oils, liquid oils and fats, solid oils and fats, waxes, and fragrances, as well as aqueous phase components such as water, water-soluble alcohols, and thickeners. When the cosmetic composition is used as a hair spray-type hair cosmetic, examples of the other components include polymerization initiators, polymeric surfactants, and basic compounds. In particular, the use of tert-octylacrylamide, tert-butylacrylamide, and the like improves the solubility of the cosmetic composition in LPG (liquefied petroleum gas). Therefore, these can be suitably used (tert-octylacrylamide) or in combination (tert-butylacrylamide) in aerosol products such as hair sprays that use LPG as hair cosmetics.

[0078] In the cosmetic composition according to the seventh embodiment, the N-substituted (meth)acrylamide (A) contained in the cosmetic composition can be brought in from a polymerizable composition containing A, or A can be brought in as a structural unit from a polymer of the polymerizable composition or a polymer of N-substituted (meth)acrylamide (A). The total content of the structural units of N-substituted (meth)acrylamide (A) and A in the cosmetic composition is preferably 1 to 80 wt%, more preferably 5 to 70 wt%, and particularly preferably 10 to 60 wt%, based on the total weight of the cosmetic composition. Such a cosmetic composition does not cause skin irritation, has moisture resistance or emulsion stability, and is stable over time, and is excellent in usability, such as smoothness, resistance to stickiness, texture, richness, and quick absorption.

[0079] An eighth embodiment of the present invention is a coating composition (hereinafter also referred to as a coating agent). The coating composition according to the eighth embodiment contains the polymerizable composition according to any one of the first to fourth embodiments or a polymer thereof. The coating composition contains an N-substituted (meth)acrylamide (A), thereby exhibiting high wettability to various substrates having a wide range of polarities, from low to high, such as organic substrates, inorganic substrates, and substrates made of organic-inorganic composite materials. A conventionally known method can be used to apply the coating composition to a substrate. After being applied to the substrate, the coating composition is cured by the aforementioned active energy rays and / or heat. The thickness of the coating composition applied to the substrate is not particularly limited, but is preferably a thickness that allows sufficient curing by active energy rays and / or heat, typically 1 to 100 μm. The resulting cured product (coating layer) has adhesion to the aforementioned various substrates and exhibits high pencil hardness and water resistance.

[0080] In the coating composition according to the eighth embodiment, the N-substituted (meth)acrylamide (A) contained in the coating composition can be brought in from a polymerizable composition containing A, and A can also be brought in as a structural unit from a polymer of the polymerizable composition and a polymer of N-substituted (meth)acrylamide (A). The total content of the N-substituted (meth)acrylamide (A) and structural units of A in the coating agent is preferably 1 to 80 wt %, more preferably 5 to 70 wt %, and particularly preferably 10 to 60 wt %, based on the total weight of the coating agent (excluding the solvent). Furthermore, from the viewpoint of further improving adhesion to various substrates, the surface tension of the N-substituted (meth)acrylamide (A) is 24.0 to 46.0 mN·m -1 It is preferable that:

[0081] The coating composition according to the eighth embodiment preferably further contains the aforementioned crosslinking agent, which improves the pencil hardness and water resistance of the coating layer. From this perspective, the content of the crosslinking agent in the total weight of the coating composition is preferably 5 to 70 wt %, more preferably 10 to 60 wt %, and particularly preferably 20 to 50 wt %. The coating composition may contain the aforementioned photopolymerization initiator, monofunctional monomers and oligomers, and non-polymerizable oligomers and polymers as other components. The content of these other components may be within a range that does not impair the aforementioned characteristics of the coating composition, and is typically 0.1 to 20 parts by weight per 100 parts by weight of the polymerizable composition. Such a coating composition has high wettability and adhesion to various substrates, and can be used to obtain coating films and other films that exhibit high surface hardness and water resistance upon curing.

[0082] A ninth embodiment of the present invention is an ink composition (hereinafter also referred to as ink). The ink composition according to the ninth embodiment contains the polymerizable composition according to any one of the first to fourth embodiments or a polymer thereof. The ink composition has high curability due to the inclusion of an N-substituted (meth)acrylamide (A). A conventionally known method can be used to apply the ink composition to a substrate. The ink viscosity at 25°C is preferably less than 500 mPa·s, and more preferably less than 100 mPa·s from the viewpoint of being able to apply the ink to a substrate by an inkjet method. After being applied to a substrate, the ink composition is cured by the above-mentioned actinic energy rays and / or heat to form an ink layer. From the viewpoint of further improving adhesion to various substrates, the surface tension of the N-substituted (meth)acrylamide (A) obtained is 24.0 to 46.0 mN·m. -1 It is preferable that:

[0083] In the ink composition according to the ninth embodiment, the N-substituted (meth)acrylamide (A) contained in the ink composition can be brought in from a polymerizable composition containing A, and A can also be brought in as a structural unit from a polymer of the polymerizable composition and a polymer of N-substituted (meth)acrylamide (A). The total content of the structural units of N-substituted (meth)acrylamide (A) in the ink is preferably 5 to 90 wt %, more preferably 10 to 85 wt %, and particularly preferably 15 to 80 wt %, based on the total weight of the ink (excluding the solvent).

[0084] The ink composition according to the ninth embodiment may further contain the crosslinking agent described above. In this case, the curability, surface drying, and water resistance of the ink layer are improved. From these viewpoints, the content of the crosslinking agent relative to the total weight of the ink composition is preferably 1 to 50 wt %, more preferably 5 to 45 wt %, and particularly preferably 10 to 40 wt %. The ink composition may further contain the above-mentioned photopolymerization initiator, monofunctional monomer and oligomer, and non-polymerizable oligomer and polymer as other components. The content of these other components may be within a range that does not impair the above-mentioned characteristics of the ink composition, and is typically 0.1 to 30 parts by weight per 100 parts by weight of the polymerizable composition. Such an ink composition has high adhesion to various substrates and excellent printing properties such as pigment dispersibility, surface drying, ejection stability, and clarity. By using this ink composition, it is possible to obtain an ink with high curability, yellowing resistance, and water resistance.

[0085] A tenth embodiment of the present invention is an ink composition for three-dimensional modeling. The ink composition for three-dimensional modeling according to the tenth embodiment contains the polymerizable composition or polymer thereof according to any one of the first to fourth embodiments, or the polymerizable composition or polymer thereof and a crosslinking agent. Because the polymerizable composition or polymer thereof according to any one of the first to fourth embodiments contains an N-substituted (meth)acrylamide (A), the ink composition for three-dimensional modeling has high curability and resistance to cure shrinkage, and the cured product has high strength and water resistance and excellent modeling precision. The ink composition for three-dimensional modeling is cured by irradiation with active energy rays and / or heat simultaneously with or immediately after formation into a predetermined shape pattern to form a thin film, and a three-dimensional model is formed by stacking these thin films. The modeling method is not particularly limited, but examples include a stereolithography method in which the ink composition is ejected by an inkjet method and cured by irradiation with active energy rays. In this case, from the viewpoint of stable ejection, the viscosity of the ink composition for three-dimensional modeling at 25°C is preferably 1 to 200 mPa·s, and the ejection temperature is preferably in the range of 20 to 100°C. The surface tension of the N-substituted (meth)acrylamide (A) is set to 24.0 to 46.0 mN m from the viewpoint of enabling the obtained three-dimensional object to exhibit a good appearance such as gloss and density. -1 It is preferable that:

[0086] In the ink composition for three-dimensional modeling according to the tenth embodiment, the N-substituted (meth)acrylamide (A) contained in the ink composition for three-dimensional modeling can be brought in from a polymerizable composition containing A, and A can also be brought in as a structural unit from a polymer of the polymerizable composition and a polymer of N-substituted (meth)acrylamide (A). The total content of the structural units of N-substituted (meth)acrylamide (A) in the ink composition for three-dimensional modeling is preferably 1 to 80% by weight, more preferably 2 to 70% by weight, and particularly preferably 5 to 60% by weight, based on the total weight of the ink for three-dimensional modeling.

[0087] The ink composition for three-dimensional modeling according to the tenth embodiment preferably further contains the aforementioned crosslinking agent. In this case, three-dimensional objects having excellent strength, water resistance, and heat resistance can be formed. From this perspective, the content of the crosslinking agent in the ink composition for three-dimensional modeling is preferably 1 to 50 wt %, more preferably 5 to 40 wt %, and particularly preferably 10 to 30 wt % based on the total weight of the ink composition for three-dimensional modeling. Furthermore, the ink composition for three-dimensional modeling may further contain the aforementioned photopolymerization initiator, monofunctional monomers and oligomers, and non-polymerizable oligomers and polymers as other components. The content of the other components may be within a range that does not impair the aforementioned characteristics of the ink composition for three-dimensional modeling, and is typically 0.1 to 20 parts by weight per 100 parts by weight of the polymerizable composition. Using such an ink composition for three-dimensional modeling, three-dimensional objects having high strength, heat resistance, and water resistance can be formed with high precision.

[0088] The polymerizable compositions according to the first to fourth embodiments may contain various additives other than those described above, as needed. Examples of such additives include thermal polymerization inhibitors, antioxidants, UV sensitizers, preservatives, phosphate esters and other flame retardants, surfactants, antistatic agents, colorants such as pigments and dyes, fragrances, antifoaming agents, fillers, silane coupling agents, surface tension modifiers, plasticizers, surface lubricants, leveling agents, softeners, organic fillers, inorganic fillers, and silica particles. These additives may be used alone or in combination of two or more. The content of these additives is not particularly limited as long as it does not adversely affect the properties of the polymerizable composition or various molded articles made from the polymerized composition, but it is preferably 5 wt % or less based on the total weight of the polymerizable composition.

[0089] The compositions according to the fifth to tenth embodiments may contain various additives other than those described above, as needed. Examples of such additives include thermal polymerization inhibitors, antioxidants, UV sensitizers, preservatives, phosphate esters and other flame retardants, surfactants, antistatic agents, colorants such as pigments and dyes, fragrances, defoamers, fillers, silane coupling agents, surface tension modifiers, plasticizers, surface lubricants, leveling agents, softeners, organic fillers, inorganic fillers, and silica particles. These additives may be used alone or in combination of two or more. The content of these additives is not particularly limited as long as it does not adversely affect the properties of various molded articles obtained from the compositions, but is preferably 30 wt% or less based on the total weight of the composition. Furthermore, water, organic solvents, and mixtures thereof may be used as solvents or diluents, as needed. The content of such solvents is not particularly limited as long as it does not adversely affect the properties of various molded articles obtained from the compositions, but is preferably 95 wt% or less based on the total weight of the composition. [Example]

[0090] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. The abbreviations for each component described in the examples and comparative examples are as follows. In the following, "parts" and "%" are all by weight unless otherwise specified. (1) N-substituted (meth)acrylamide (A) CHAA: N-cyclohexyl acrylamide (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 32.3 mN m -1 ) CHMAA: N-cyclohexyl-N-methylacrylamide (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 32.5 mN m -1 ) ACP: N-acryloylpiperidine (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 35.7 mN m -1 ) ACMP: N-acryloyl-4-methylpiperidine (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 31.6 mN m -1 ) ACDMP: N-acryloyl-3,5-dimethylpiperidine (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 28.6 mN m -1 ) NOAA: n-octylacrylamide (registered trademark "Kohshylmer") (waxy state at room temperature, surface tension: 30.0 mN m -1 ) TOAA: tert-octylacrylamide (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 29.1 mN m -1 ) EHAA: N-(2-ethylhexyl)acrylamide (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 29.7 mN m -1 ) DEHAA: N,N-di-2-ethylhexyl acrylamide (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 31.0 mN m -1 ) LMAA: N-lauryl methacrylamide (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 31.2 mN m -1 ) OLAA: N-oleyl acrylamide (registered trademark "Kohshylmer") (liquid at room temperature, surface tension: 32.3 mN m -1 ) STAA: N-stearyl acrylamide (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 31.9 mN m -1 ) AAPB: 3-acrylamidophenylboronic acid (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 24.0 mN m -1 ) DPAA: Dopamine acrylamide (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 36.5 mN m -1 ) PHAM: Phenylacrylamide (registered trademark "Kohshylmer") (solid at room temperature, surface tension: 45.3 mN m -1 ) (2) Monofunctional Monomer TBAA: tert-butylacrylamide BA: butyl acrylate 2EHA: 2-ethylhexyl acrylate STA: Stearyl acrylate OLA: Oleyl acrylate EA: Ethyl acrylate HEA: Hydroxyethyl acrylate 4HBA: 4-hydroxybutyl acrylate PEA: Phenoxyethyl acrylate IBOA: Isobornyl acrylate THFA: Tetrahydrofurfuryl acrylate AAc: acrylic acid VOZO: 2-vinyl-2-oxazoline (registered trademark "Kohshylmer") MHAGE: N-methyl-N-hydroxyethyl acrylamide glycidyl ether (registered trademark "Kohshylmer") GA: Glycidyl acrylate (registered trademark "Kohshylmer") "HEAA": Hydroxyethylacrylamide (registered trademark "Kohshylmer", "HEAA") "DMAA": Dimethylacrylamide (registered trademark "Kohshylmer", "DMAA") "DEAA": Diethylacrylamide (registered trademark "Kohshylmer", "DEAA") "NIPAM": Isopropylacrylamide (registered trademark "Kohshylmer", "NIPAM") DAAM: Diacetone acrylamide (registered trademark "Kohshylmer") (3) Polyfunctional monomers, etc. (polyfunctional monomers, oligomers) PETA: Pentaerythritol triacrylate DPHA: Dipentaerythritol hexaacrylate HDDA: 1,6-hexanediol diacrylate TPGDA: Tripropylene glycol diacrylate UV-3000B: Bifunctional urethane acrylate (Shiko, manufactured by Mitsubishi Chemical Corporation) UV-6640B: Difunctional urethane acrylate (Shiko, manufactured by Mitsubishi Chemical Corporation) Quick Cure 7100: UV-curable urethane oligomer (registered trademark "Quick Cure", manufactured by KJ Chemicals) Quick Cure 8100: UV-curable urethane oligomer (registered trademark "Quick Cure", manufactured by KJ Chemicals) (4) Other O-184: Omnirad 184 (photopolymerization initiator, manufactured by IGM Resins BV) O-1173: Omnirad 1173 (photopolymerization initiator, manufactured by IGM Resins BV) TPO: Omnirad TPO (photopolymerization initiator, manufactured by IGM Resins BV) HDI: Hexamethylene diisocyanate (crosslinking agent) HHPA: Hexahydrophthalic anhydride (crosslinking agent) AIBN: Azobisisobutyronitrile (radical polymerization initiator) V-601: Azobis(isobutyrate) dimethyl (radical polymerization initiator) KE-359: Hydrogenated rosin (Tackyfire, non-polymerizable polymer, manufactured by Arakawa Chemical Industries) VS-1063: Styrene acrylic resin (non-polymerizable oligomer, manufactured by Seiko PMC Corporation) VS-1057: Acrylic resin (non-polymerizable polymer, manufactured by Seiko PMC) 50HB-55: Polyoxyethylene (2) polyoxypropylene (2) butyl ether (m = 2, n = 2, molecular weight 240) (manufactured by Sanyo Chemical Industries, Ltd.) 50HB-100: Polyoxyethylene (5) polyoxypropylene (5) butyl ether (m = 5, n = 5, molecular weight 540) (manufactured by Sanyo Chemical Industries, Ltd.) 50HB-260: Polyoxyethylene (10) polyoxypropylene (7) butyl ether (m = 10, n = 7, molecular weight 880) (manufactured by Sanyo Chemical Industries, Ltd.) AMP: 2-amino-2-methyl-1-propanol PME4000: Blenmar PME-4000 (NOF Corporation) (5) Base material PE: Polyethylene plate and film (surface tension: 22.6 mN m -1 ) PP: Polypropylene plate and film (surface tension: 22.6 mN m -1 ) PC: Polycarbonate plate and film (surface tension: 34.0 mN m -1 ) ABS: Acrylonitrile-butadiene-styrene copolymer synthetic resin plate (surface tension: 34.0 mN m -1 ) PI: Polyimide plate and film (surface tension: 40.0 mN m -1 ) PMMA: Polymethyl methacrylate plate and film (surface tension: 36.0 mN m -1 ) PET: Highly adhesive polyethylene terephthalate plate and film (surface tension: 59.0 mN m -1 ) SPCC: Cold-rolled steel sheet (surface tension: 45.0 mN m -1 ) SST: Stainless steel plate (surface tension: 40.0 mN m -1 ) Cu: Copper plate (Surface tension: 38.0mN m -1 ) Al: Aluminum plate (surface tension: 36.0 mN m -1 ) GL: transparent glass plate (surface tension: 40.0 mN m -1 ) PI-silica: Silica particle dispersed polyimide plate and film (surface tension: 40.0 mN m -1 )

[0091] Example 1 (Production and Evaluation of Polymer of N-Substituted (Meth)acrylamide (A)) A 500 mL flask equipped with a thermometer, stirrer, reflux condenser, and nitrogen inlet tube was charged with 30 g of N-substituted (meth)acrylamide (A) (CHAA), 44 g of 2EHA, 20 g of NIPAM, 5 g of HEA, and 1 g of AIBN, and 100 g of ethyl acetate as solvent. After uniform mixing at room temperature, the atmosphere was purged with nitrogen for 30 minutes. The reaction mixture was then heated to 70°C and polymerized for 8 hours. After completion of the reaction, ethyl acetate was added to the reaction mixture to prepare a polymer solution with a 30% solids content. The viscosity of the polymer solution at 25°C was measured using a cone-plate viscometer (Toki Sangyo Co., Ltd., RE550 model) according to JIS K5600-2-3 and found to be 4250 mPa·s. A 30 g aliquot was removed from the polymer solution, and the volatile components in the solution were completely removed to obtain the polymer. The resulting polymer was then dissolved in tetrahydrofuran (THF) to prepare a 0.5 wt% THF solution of the polymer, which was then allowed to stand overnight. The THF solution was then filtered through a 0.45 μm membrane filter, and the filtrate was subjected to gel permeation chromatography (GPC) using a Shimadzu Prominence GPC system, a Shodex KF-806L column, and THF as the eluent. The weight-average molecular weight (Mw) of the polymer was calculated to be 960,000 in terms of polystyrene.

[0092] (Water resistance evaluation of polymers) Similarly, 30 g of the polymer solution was removed, the volatile components were completely removed, and the polymer was dried under vacuum at 60 °C for 24 hours to obtain a dried polymer. 5 g of the dried polymer was then accurately weighed into a weighed plastic petri dish, which was used as the dry weight of the polymer. The petri dish containing the polymer was placed in a thermo-hygrostat and incubated at 30 °C and 90% humidity for 24 and 48 hours. The weight of the polymer immediately after removal from the thermo-hygrostat was measured to confirm that the polymer had reached saturated water absorption, and this was used as the saturated weight of the polymer. The saturated water absorption was calculated using the following formula, and the water resistance of the polymer was evaluated using the following four-point scale. The results are shown in Table 1. Saturated water absorption rate (%) = (weight of saturated state - weight of dry state) / weight of dry state × 100% ◎: Saturated water absorption is 5% or more. ○: The saturated water absorption rate is more than 5% but is 7% or less. △: The saturated water absorption rate is more than 7% but is 10% or less. ×: Saturated water absorption exceeds 10%.

[0093] Examples 2 to 12 and Comparative Examples 1 to 3 (Production of Polymers of N-Substituted (Meth)acrylamide (A) and Other Polymers) The types and contents of N-substituted (meth)acrylamide, monofunctional monomer, and polymerization initiator were changed as shown in Table 1, and polymerization reactions were carried out in Examples 2 to 12 and Comparative Examples 1 to 3 in the same manner as in Example 1 to obtain polymer solutions with a solid content of 30%. The viscosity of the obtained polymer solutions and the molecular weight of the polymer were measured in the same manner as in Example 1, and the results are shown in Table 1.

[0094] [Table 1]

[0095] Examples 13 to 28 and Comparative Examples 4 to 7 (Preparation and Evaluation of Polymerizable Compositions) The N-substituted (meth)acrylamide (A) and other components used in this embodiment were weighed in the proportions shown in Table 2 and mixed uniformly at room temperature to prepare polymerizable compositions for Examples and Comparative Examples. The transparency and wettability of the resulting polymerizable compositions to various substrates were evaluated using the methods described below, and the results are shown in Table 2. The polymerizable compositions of Examples 15, 16, 18, and 21 were polymerizable resin compositions for thermal polymerization, corresponding to Examples 4, 2, 8, and 3 shown in Table 1, respectively, and the properties of the resulting polymers are also shown in Table 1. The polymerizable resin compositions other than those for thermal polymerization were polymerizable resin compositions for active energy ray curing, and the curability and water resistance of the resulting cured products were evaluated using the methods described below, and the results are shown in Table 2. In Example 14, the composition was cured by irradiation with an electron beam (EB) instead of ultraviolet light. A Curetron EBC-200-AA3 EB irradiation device manufactured by Nissin High Voltage Corporation was used (accelerating voltage: 200 kV, exposure dose: 20 kGy).

[0096] [Table 2]

[0097] (Transparency Assessment) The various polymerizable compositions obtained were allowed to stand overnight at 23° C., and the state of the compositions was visually observed, and the transparency was evaluated according to the following four-level scale. ◎: High transparency, no cloudiness or separation observed. Good: High transparency, but slight cloudiness observed. △: No layer separation, but cloudy. ×: Cloudy and further layer separation occurred.

[0098] (Wettability evaluation) The obtained various polymerizable compositions were applied to various substrates using a bar coater (RDS 3), and the degree of repelling of the coating film was visually observed, and the wettability was evaluated according to the following four levels. ⊚: No repelling and a uniform coating film. ◯: There is very little repelling, but the coating film is almost uniform. △: There is some cissing, but the coating film is generally uniform overall. ×: There is a lot of repelling and the coating film is non-uniform.

[0099] (Curing evaluation) Curability was measured by placing a 100 μm thick PET film (Cosmoshine A4100, polyester film, manufactured by Toyobo Co., Ltd.) on a horizontally placed glass plate with the easy-adhesion side facing up, and then using a bar coater No. 30, applying the active energy ray-curable polymerizable resin composition prepared in each Example and Comparative Example. Then, a 50 μm thick easy-release PET film (E7002, polyester film, manufactured by Toyobo Co., Ltd.) was placed on top of the applied film, and the applied film was irradiated with ultraviolet light at a predetermined integrated light intensity (apparatus: MUVBA-0.3×0.3×0.5, tabletop batch-type UV-LED curing apparatus manufactured by ITEC System Co., Ltd., wavelength 405 nm, illuminance (UV-V) 50 mW / cm). 2) to cure the resin composition. The release PET film was then removed to obtain test pieces of the cured product for evaluating curability for the Examples and Comparative Examples. The tackiness of the surface of the resulting cured product was evaluated, and the following evaluation was performed based on the integrated light amount at which the tackiness disappeared. ◎: Accumulated light intensity 200mJ / cm 2 Tack disappears below ○: Accumulated light intensity 200mJ / cm 2 More than 500mJ / cm 2 Tack disappears below △: Accumulated light intensity 500mJ / cm 2 More than 1000mJ / cm 2 Tack disappears below ×: The adhesiveness disappears when the integrated light intensity is 1000 mJ / cm or more (including cases where the adhesiveness does not disappear)

[0100] (Water resistance evaluation of cured product) A silicone spacer (30 mm long x 15 mm wide x 1 mm thick) was placed on a glass plate (50 mm long x 50 mm wide x 5 mm thick), and the active energy ray-curable polymerizable resin composition prepared in each example and comparative example was poured into the spacer, followed by ultraviolet irradiation (700 mW / cm 2 , 2000mJ / cm 2 ) to produce a cured sheet. The resulting sheet was cut into 3 cm squares, dried under vacuum at 60°C for 24 hours, and accurately weighed as a dry sheet, which was used as the dry weight of the cured product. The dried sheet was immersed in deionized water at 30°C, and after 24 and 48 hours, it was weighed immediately after being removed from the deionized water to confirm that the sheet had reached saturated water absorption, and this was used as the weight of the cured product in saturated water absorption state. The saturated water absorption rate was calculated using the following formula, and the water resistance of the cured product was evaluated using the following four-level scale. Saturated water absorption rate (%) = (weight of saturated state - weight of dry state) / weight of dry state × 100% ◎: Saturated water absorption is 5% or more. ○: The saturated water absorption rate is more than 5% but is 7% or less. △: The saturated water absorption rate is more than 7% but is 10% or less. ×: Saturated water absorption exceeds 10%.

[0101] Examples 29 to 70 and Comparative Examples 8 to 20 (Preparation and Evaluation of Pressure-Sensitive Adhesive Compositions) (Examples 29 to 40 and Comparative Examples 8 to 10) The polymer solutions obtained in Examples 1 to 12 and Comparative Examples 1 to 3 were applied to a heavy-release separator (silicone-coated PET film) to a dry thickness of 25 μm, and then dried at 90°C for 2 minutes to form a pressure-sensitive adhesive layer. The sheet was then left in an environment at a temperature of 23°C and a relative humidity of 50% for one day to obtain a test pressure-sensitive adhesive sheet (Type a-1). Furthermore, the Type a test pressure-sensitive adhesive sheets (those containing unsaturated bonds derived from oleyl groups in the corresponding polymers) prepared in Examples 30, 35, 38, and Comparative Example 10 were irradiated with ultraviolet light (apparatus: Inverter-type conveyor device ECS-4011GX manufactured by Eye Graphics, metal halide lamp: M04-L41 manufactured by Eye Graphics, ultraviolet irradiance: 700 mW / cm). 2 , Accumulated light intensity: 1000mJ / cm 2 ) to obtain a test pressure-sensitive adhesive sheet (type a-2).

[0102] (Examples 41 to 48 and Comparative Example 11) The polymer solutions obtained in Examples 1, 4, 6, 8, and 12 and Comparative Example 1, and HDI as a crosslinker, were weighed out to the solid content shown in Table 4 and uniformly mixed. As described above, the solution was applied to a PET film so that the dried thickness would be 25 μm, and then dried at 90°C for 2 minutes to form a pressure-sensitive adhesive layer. The solution was then aged in a 40°C thermostatic chamber for 3 days and then placed in an environment at 23°C and 50% relative humidity for 1 day to obtain a test pressure-sensitive adhesive sheet (Type b-1). The polymer solutions obtained in Examples 7, 9, and 10 and polyacrylic acid (PAAc, Fujifilm Wako Pure Chemical Industries, Ltd., average molecular weight 5,000) as a crosslinker were weighed out to the solid content shown in Table 4 and uniformly mixed. As described above, the solution was applied to a PET film so that the dried thickness would be 25 μm, and then dried at 90°C for 2 minutes to form a pressure-sensitive adhesive layer. Thereafter, the sheet was aged in a thermostatic chamber at 40°C for 3 days, and then placed in an environment at a temperature of 23°C and a relative humidity of 50% for 1 day to obtain a test pressure-sensitive adhesive sheet (type b-2).

[0103] (Examples 49 to 53 and Comparative Examples 12 and 13) The polymer solutions obtained in Examples 2, 4, 5, 7, 8, and 11 and Comparative Examples 2 and 3 were weighed out, and the monofunctional monomer, the multifunctional monomer and / or multifunctional oligomer as a crosslinking agent, the photopolymerization initiator, and other components were weighed out in the amounts shown in Table 5 and uniformly mixed. As in the above, the solution was applied to a PET film that would have a thickness of 25 μm after drying, and dried at 90°C for 2 minutes to form a pressure-sensitive adhesive layer. Thereafter, the solution was irradiated with ultraviolet light (apparatus: Inverter-type conveyor apparatus ECS-4011GX manufactured by Eye Graphics, metal halide lamp: M04-L41 manufactured by Eye Graphics, ultraviolet irradiance: 700 mW / cm 2 , Accumulated light intensity: 1000mJ / cm 2 ), cured, and left in an environment of 23°C and 50% relative humidity for one day to obtain a test pressure-sensitive adhesive sheet (type c).

[0104] (Examples 54 to 65 and Comparative Examples 14 to 17) The polymerizable compositions obtained in Examples 13, 14, 17, 19, 20, and 22 to 28 and Comparative Examples 4 to 7 were applied to a heavy release separator (silicone-coated PET film), and the light release separator (silicone-coated PET film) was laminated using a tabletop roll laminator (RSL-382S manufactured by Royal Sovereign) so as not to trap air bubbles, so that the adhesive layer had a thickness of 25 μm. The laminate was then irradiated with ultraviolet light (apparatus: inverter-type conveyor device ECS-4011GX manufactured by Eye Graphics, metal halide lamp: M04-L41 manufactured by Eye Graphics, ultraviolet irradiance: 700 mW / cm 2 , Accumulated light intensity: 1000mJ / cm 2 ) to produce an optical transparent adhesive sheet (type d).

[0105] (Examples 66 to 72 and Comparative Examples 18 to 20) The polymer solutions or polymerizable compositions obtained in Examples 1, 6, 8, 12 to 14, 19, and 24 and Comparative Examples 1, 4, and 5, HDI or a polyfunctional monomer and / or polyfunctional oligomer as a crosslinking agent, a photopolymerization initiator, and other components were weighed out in the amounts shown in Table 7 and mixed uniformly. Pressure-sensitive adhesive sheets were prepared in the same manner as in Type c (when a polymer was used) or Type d (when a polymerizable composition was used) and cured by ultraviolet light. The sheets were then aged in a 40°C thermostatic chamber for three days and then placed in an environment at 23°C and 50% relative humidity for one day to obtain test pressure-sensitive adhesive sheets (Type e).

[0106] The properties of the various pressure-sensitive adhesive sheets produced were evaluated by the following methods, and the results are shown in Tables 3 to 7. (Transparency evaluation of adhesive sheets) The total light transmittance of the glass substrate was measured using a haze meter (NDH-2000, manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with JIS K 7105. The above adhesive layer was transferred to a glass substrate under conditions of a temperature of 23°C and a relative humidity of 50%, and the total light transmittance of the glass substrate and adhesive layer was measured. The transmittance of the glass plate was then subtracted to calculate the transmittance of the adhesive layer itself, and the transparency was evaluated into four levels as shown below. ◎: Transmittance is 90% or more ○: Transmittance is 85% or more and less than 90% △: Transmittance is 50% or more and less than 85% ×: Transmittance is less than 50%

[0107] (Adhesion evaluation) The active energy ray-curable adhesive composition prepared above was coated onto various plate-shaped substrates (substrates), and the substrates were laminated using a tabletop roll laminator (RSL-382S manufactured by Royal Sovereign) with a light-release separator (silicone-coated PET film) to avoid trapping air bubbles, so that the adhesive layer had a thickness of 5 μm. The substrates were then irradiated with ultraviolet light (apparatus: inverter-type conveyor device ECS-4011GX manufactured by Eye Graphics, metal halide lamp: M04-L41 manufactured by Eye Graphics, ultraviolet irradiance: 700 mW / cm). 2 , Accumulated light intensity: 2000mJ / cm 2) was then removed, yielding a pressure-sensitive adhesive sheet consisting of the adhesive layer and substrate. Using the resulting pressure-sensitive adhesive sheet, 100 1 mm squares were created in accordance with JIS K 5600, and cellophane tape was attached to each square. The tape was then peeled off in one go, and the number of squares with the adhesive layer remaining on the substrate side was counted, and the adhesion was evaluated according to the following criteria. ◎: No peeling after 100 pieces 〇: 95 to 99 pieces, no peeling △: 70 to 94 pieces, no peeling ×: 0 to 69 pieces, no peeling

[0108] (Adhesion strength evaluation) The adhesive layer was transferred to various film or plate substrates at a temperature of 23°C and a relative humidity of 50%, 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 atmosphere. The 180° peel strength (N / 25 mm) was then measured at a peel rate of 300 mm / min using a tensile tester (Tensilon RTA-100, manufactured by ORIENTEC) in accordance with JIS Z0237. ◎:30(N / 25mm) or more ○: 15 (N / 25mm) or more, less than 30 (N / 25mm) △: 8 (N / 25mm) or more, less than 15 (N / 25mm) ×: Less than 8 (N / 25mm)

[0109] (Contamination resistance (reworkability) evaluation) An adhesive sheet was prepared in the same manner as in the measurement of adhesive strength described above, and after leaving it at 80°C for 24 hours, the surface of the base film was visually inspected for contamination (remaining adhesive layer (glue)) after peeling off the adhesive sheet. ◎: No contamination (no adhesive residue). ○: There is very little contamination. △: Slight contamination. ×: Contamination occurs (glue remains).

[0110] (Yellowing resistance evaluation) An adhesive sheet was prepared in the same manner as in the measurement of adhesive strength described above, and set in a xenon fade meter (SC-700-WA: manufactured by Suga Test Instruments Co., Ltd.). 2 After 120 hours of irradiation with ultraviolet light of an intensity of 10 ... ⊚: No yellowing was observed visually. ○: Yellowing is very slight and visible. △: Yellowing can be visually confirmed. ×: Obvious yellowing is visible.

[0111] (Durability evaluation) An adhesive sheet was prepared in the same manner as in the measurement of adhesive strength described above, and after holding it for 100 hours under conditions of a temperature of 85°C and a relative humidity of 85%, the adhesive layer was visually observed and evaluated for any lifting, peeling, bubbles, or cloudiness. ◎: Transparent, no floating, peeling or bubbles. ○: There is a slight cloudiness, but no lifting, peeling, or bubbles. △: Slight cloudiness, lifting, peeling, or bubbles. ×: Severe cloudiness, lifting, peeling, or bubbles.

[0112] [Table 3]

[0113] [Table 4]

[0114] [Table 5]

[0115] [Table 6]

[0116] [Table 7]

[0117] Examples 73 to 82 and Comparative Examples 21 to 24 (Preparation and Evaluation of Adhesive Compositions) The polymers obtained in Examples 1-4, 6, 8, 9, and 11 and Comparative Examples 1 and 2 and / or the polymerizable compositions obtained in Examples 13, 14, 19, 20, 25-27 and Comparative Examples 4 and 5, crosslinkers, and other components were weighed out to the solid content shown in Table 8 and mixed uniformly at room temperature to obtain a uniform mixture. Two identical or different plate-shaped substrates measuring 100 mm long, 25 mm wide, and 1 mm thick were used, and the mixture was uniformly coated onto any one of them. When the mixture contained a solvent, a larger amount of the mixture was applied so that the dried thickness would be similar to that without the solvent, and the mixture was dried at 90°C for 2 minutes. Then, according to JIS K 6850, the other plate-shaped substrate was placed on the coated mixture and bonded together so that the overlapping area was 12.5 mm long and 25 mm wide. The thickness of the adhesive layer was adjusted to 100 μm using a spacer, and bonded test specimens were prepared. Thereafter, UV or EB irradiation was performed from the top surface of the bonded transparent or translucent substrate in the same manner as in the preparation of the adhesive layer. In Table 8, for examples where the curing method is listed as UV or EB, the test specimens irradiated with UV rays or EB rays, respectively, were used as adhesive test specimens. For examples where the curing method is listed as UV heat or EB heat, the test specimens irradiated with UV rays or EB rays, respectively, were further heated at 40°C for 72 hours, and the resulting test specimens were used as adhesive test specimens. For examples where the curing method is listed as heat, the prepared test specimens were not irradiated with UV rays or EB rays, but were heated at 40°C for 72 hours, and the resulting test specimens were used as adhesive test specimens. Furthermore, the adhesive test specimens obtained were evaluated for adhesive strength and impact resistance using the following methods, and the results are shown in Table 8.

[0118] (Adhesion strength evaluation) Using the obtained adhesive test piece, the tensile shear strength was measured in accordance with JIS K 6850 using a Tensilon RTA-100 tester (manufactured by ORIENTEC) at a pulling rate of 10 mm / min. ◎: Tensile shear strength is 20 MPa or more. ◯: The tensile shear strength is 15 MPa or more and less than 20 MPa. △: The tensile shear strength is 10 MPa or more and less than 15 MPa. ×: The tensile shear strength is less than 10 MPa.

[0119] (Impact resistance evaluation) The adhesive test pieces obtained were used to measure impact peel adhesive strength in accordance with JIS K6855 using an impact tester No. 511 (manufactured by Mize Testing Instruments Co., Ltd.). ◎: Impact peel adhesive strength is 20KJ / m 2 That's all. ○: Impact peel adhesive strength is 15KJ / m 2 More than 20KJ / m 2 is less than. △: Impact peel adhesive strength is 10KJ / m 2 More than 15KJ / m 2 is less than. ×: Impact peel adhesive strength is 10KJ / m 2 is less than.

[0120] [Table 8]

[0121] Examples 83 to 97 and Comparative Examples 25 to 28 (Production and Evaluation of Cosmetic Compositions) Examples 83 to 89 and Comparative Examples 25 and 26 (Production and Evaluation of Hair Cosmetic Compositions) A 1-liter four-neck flask equipped with a reflux condenser, thermometer, nitrogen purge tube, and stirrer was charged with 100 g of ethanol. The polymers obtained in Table 1, the polymerizable compositions obtained in Table 2, and other ingredients were added in the proportions (solids basis) shown in Table 9. The polymerization reaction was then carried out under reflux (approximately 80°C) for 8 hours under a nitrogen stream. After the polymerization reaction was completed, 2-amino-2-methyl-1-propanol (AMP) (solids basis) diluted with an equal amount of ethanol as a basic compound was added in the proportions shown in Table 9 at 50°C to neutralize the mixture. The mixture was then further diluted with ethanol to a solids content of 40%, yielding a base for hair cosmetics. The resulting base for hair cosmetics, ethanol, and liquefied petroleum gas were mixed in a weight ratio of 7.5:42.5:50 and sealed in a spray can to obtain a hair cosmetic in hair spray form. The obtained hair cosmetics were evaluated for moisture resistance, smoothness, anti-stickiness, texture, and stability over time by the methods described below, and the results are shown in Table 9. The polymerizable composition of Example 23 in Example 83 and the polymerizable composition of Example 28 in Example 84 were used without the polymerization initiator.

[0122] (Set retention (humidity resistance) evaluation using curl retention method) 0.4 g of the test formulation was sprayed onto a hair bundle measuring 22 cm in length and weighing 2 g, and then spread over the entire hair with a comb. The hair bundle was then wound around curlers measuring 2.2 cm in diameter and dried at 20°C for 20 hours. The hair bundle was unwound into a spiral, attached to a vertically-standing glass plate with a scale, and left in a thermo-hygrostat kept at 30°C and 95% RH. After 10 hours, the position of the hair tip was recorded, and curl retention was calculated using the following formula and evaluated according to the following criteria. Curl retention (%) = {(L-Lt) / (L-L0)} x 100 L: Length of the test hair when stretched Lt: The tip position of the test hair after 10 hours in a constant temperature and humidity chamber L0: Tip position of the test hair before placing it in the temperature and humidity chamber ◎: 80% or more ○: 65% or more but less than 80% △: 50% or more but less than 65% ×: Less than 50%

[0123] (Smoothness evaluation) The test formulation was sprayed onto a dry hair bundle measuring 22 cm in length and weighing 2 g, and an in-house monitor manually unraveled the hair bundle from immediately after spraying until it dried (before drying) and after drying (after drying), determining the ease of passing through the hair bundle and rating it according to the following criteria. ⊚: No tack or creaking before or after drying, and smooth. ◯: Smoothness is good before drying, but there is slight tack or creaking after drying. △: There is slight tack or creak before drying, and there is strong tack or creak after drying. ×: There is a lot of tack and creaking before and after drying, making it unsuitable for practical use.

[0124] (Sticky resistance evaluation) A dry hair bundle was prepared, sprayed with the test formulation, and the sticky feeling when the hair bundle after drying was held in the palm of the hand was evaluated. ◎: When touched with the fingers, it is not sticky and feels smooth. ○: Slightly sticky when touched with fingers. △: Sticky when touched with fingers. ×: When touched with fingers, it becomes sticky and difficult to remove from fingers.

[0125] (Feel evaluation) As in the case of evaluating humidity resistance, the feel of the prepared hair when touched with the hands was evaluated by a sensory test using in-house monitors as follows, and the same test was conducted one day later to evaluate the change over time. The evaluation criteria are shown below. ⊚: Smooth and dry to the touch. ○: There was a slight stiffness, but it was satisfactory. △: Stiff or sticky. ×: Quite stiff or very sticky.

[0126] (Evaluation of stability over time) The test formulation was allowed to stand at room temperature for one month, and then the degree of separation of the formulation components was visually observed and evaluated as follows: ⊚: No separation occurred at all. ○: Slight separation occurred, and no separation occurred after shaking for 1 minute and leaving to stand for 7 days. △: Slight separation occurred, and it was possible to redisperse it by shaking for 1 minute, but separation occurred again after 1 hour. ×: Separation occurred and the particles could not be dispersed again even after shaking.

[0127] [Table 9]

[0128] Examples 90 to 97 and Comparative Examples 27 and 28 (Production and Evaluation of Skin Cosmetic Compositions) A 1-liter three-neck flask equipped with a reflux condenser and nitrogen inlet tube was charged with 100 g of a water-ethanol mixed solvent (weight ratio 75:25), and the polymerized product obtained in Table 1, the polymerizable composition obtained in Table 2, and other ingredients were added in the proportions (solids content equivalent) listed in Table 10. After thorough dissolution or dispersion, the atmosphere was replaced with nitrogen for 20 minutes to remove dissolved oxygen. The mixture was then stirred in an oil bath at 65-70°C for 8 hours to carry out the polymerization reaction. After polymerization was completed, the polymerized solution was returned to room temperature, and the resulting dispersion was used as a cosmetic raw material. 1 g of carboxyvinyl polymer (a water-phase component) and 0.6 g of potassium hydroxide were added to ion-exchanged water and mixed, and 100 g of the cosmetic raw material, which had been separately dispersed in ion-exchanged water, was added and mixed. The total amount of ion-exchanged water used was 500 g. After uniformly dispersing the cosmetic raw materials and aqueous phase components, 100 parts of liquid paraffin, 100 g of glycerin tri-2-ethylhexanoate, and dimethylpolysiloxane (6cs) were added as oil phase components, and the mixture was sheared and mixed using a homomixer until uniform, yielding an oil-in-water emulsion cosmetic. The emulsion stability, skin irritation, usability, and stability over time of the obtained oil-in-water emulsion cosmetic were evaluated using the methods described below, and the results are shown in Table 10. The polymerizable composition of Example 13 in Example 90, the polymerizable composition of Example 17 in Example 91, the polymerizable composition of Example 19 in Example 95, and the polymerizable composition of Example 28 in Example 97 were used without the polymerization initiator.

[0129] (Emulsion stability (emulsion particles) evaluation) The emulsion particles of the sample were observed under an optical microscope. ◎: The emulsified particles were uniform, and no coalescence or aggregation was observed. ○: The emulsified particles were almost uniform, but no coalescence or aggregation was observed. △: The emulsified particles were almost uniform, but slight coalescence and aggregation were observed. ×: The emulsified particles were not uniform, and significant coalescence and aggregation were observed.

[0130] (skin irritation test) Ten sensitive skin panelists applied an occlusive patch to the inner upper arm for 24 hours, and the skin condition was evaluated according to the following criteria. 0: No abnormalities were observed. 1: Slight redness is observed. 2...Redness is observed. 3...Redness and papules are observed. The evaluation criteria for the "skin irritation test" are as follows: ◎: The average value of 10 panelists is between 0 and 0.15 ○: The average value of 10 panelists is 0.15 or more and less than 0.2 △: The average value of 10 panelists is between 0.2 and 0.3 ×: The average value of 10 panelists is 0.3 or more

[0131] (Usability evaluation) A panel of 10 experts evaluated the feel of the samples when they were applied to the skin ("non-stickiness," "richness," and "quick absorption") using the following criteria. ◎: Seven or more people answered "good" or "can feel it." ○: 5 to 7 people answered "good" or "can feel it." △: 3 to 5 people answered "good" or "can feel it." ×: Two or fewer people answered "good" or "realizable."

[0132] (Evaluation of stability over time) The condition of the oil-in-water emulsion cosmetic was observed with the naked eye one month after production. ◎: The sample maintains the emulsified state at the time of production. ○: Some settling / floating was observed, but the sample remained mostly emulsified. △: Emulsified particles settle / float, and coalescence of particles is also observed. ×: Emulsified particles in the sample settle / float and coalesce, and the oil phase is completely separated.

[0133] [Table 10]

[0134] Examples 98 to 105 and Comparative Examples 29 and 30 (Preparation and Evaluation of Coating Compositions) The polymers obtained in Table 1, the polymerizable compositions obtained in Table 2, and other components were weighed out according to the proportions (solid content equivalent) shown in Table 11, and mixed uniformly at room temperature to prepare coating compositions. Coating test pieces (coating films) were prepared by the following method, and the wettability to various substrates (substrates), pencil hardness of the coating films, and adhesion were evaluated. The results are shown in Table 11.

[0135] (Preparation of coating test pieces (paint film)) The coating composition was dropped in a strip onto the leading edge of various substrates (bases), applied using a bar coater (RDS 3), and dried at 90°C for 2 minutes. The coating was then cured using the curing method (UV, EB, heat, UV heat, EB heat) shown in Table 11 to form a coating layer on the substrate. The test pieces were then left in an environment at a temperature of 23°C and a relative humidity of 50% for one day to obtain coated test pieces for evaluation. The UV curing method involved irradiating the coated surface with ultraviolet light facing upward (device: Eye Graphics inverter conveyor device ECS-4011GX, metal halide lamp: Eye Graphics M04-L41, ultraviolet irradiance: 700 mW / cm). 2 , Accumulated light intensity: 1000mJ / cm 2) and hardening, while EB hardening is a method of hardening by irradiation with electron beams instead of ultraviolet light. The EB irradiator used was a Curetron EBC-200-AA3 manufactured by Nissin High Voltage Corporation (accelerating voltage: 200 kV, exposure dose: 20 kGy). UV thermal hardening is a method of UV hardening followed by aging at 40°C for 72 hours to complete the crosslinking reaction by the crosslinking agent. EB thermal hardening is a method of EB hardening followed by aging at 40°C for 72 hours to complete the crosslinking reaction by the crosslinking agent.

[0136] (Evaluation of wettability of coating composition) The coating composition was applied to various substrates using a bar coater (RDS 3), and the degree of repellency of the coating liquid was visually observed. ⊚: No repelling and a uniform coating film. ◯: There is very little repelling, but the coating film is almost uniform. △: There is some cissing, but the coating film is generally uniform overall. ×: There is a lot of repelling and the coating film is non-uniform.

[0137] (Pencil hardness evaluation) The evaluation was based on JIS K 5400 8.4 manual scratching method (1990 edition).

[0138] (Adhesion evaluation) In accordance with JIS K 5600, 100 squares of 1 mm square were created, cellophane tape was attached, and the tape was peeled off in one go. The number of squares that had adhesive layer remaining on the substrate side was counted, and the adhesion was evaluated according to the following criteria. ◎: No peeling after 100 pieces 〇: 95 to 99 pieces, no peeling △: 70 to 94 pieces, no peeling ×: 0 to 69 pieces, no peeling

[0139] [Table 11]

[0140] Examples 106 to 113 and Comparative Examples 31 to 33 The polymer obtained in Table 1, the polymerizable composition obtained in Table 2, and other ingredients were weighed out according to the proportions (solids content equivalent) shown in Table 12, and mixed uniformly at room temperature to prepare an ink composition. The viscosity of the prepared ink composition was measured, and the raw material dispersibility was evaluated. Inkjet printing was also performed using the prepared ink composition, and the physical properties of the resulting prints were evaluated. Note that the clear ink composition did not contain a pigment or a pigment dispersant, and the black ink composition contained the pigment Pignent Black 7, and evaluations were performed with and without the pigment dispersant AJISPER PB821. The evaluation results are summarized in Table 12.

[0141] (Viscosity measurement and evaluation) The viscosity of the ink composition was measured in accordance with JIS K5600-2-3 using a cone-plate viscometer (RE550 viscometer manufactured by Toki Sangyo Co., Ltd.) As an ink composition for inkjet printing, the viscosity was evaluated into the following four levels. ◎: Less than 5 to 100 mPa·s ○: Less than 100 to 500 mPa·s △: 500 to less than 2000 mPa·s ×:2000mPa·s or more

[0142] (Pigment dispersibility evaluation) The prepared ink compositions were visually observed for pigment aggregation and precipitation immediately after preparation and after standing for 2 months, and the pigment dispersibility was evaluated into the following four levels. ⊚: No aggregation or precipitation of the pigment was observed immediately after preparation or after leaving it to stand for 2 months. ◯: No precipitation of pigment was observed immediately after preparation, but slight precipitation of pigment was observed after leaving it to stand for 2 months. △: Slight aggregation and precipitation of pigments was observed immediately after preparation, but after leaving the mixture to stand for 2 months, aggregation and precipitation of pigments was clearly observed. ×: Pigment aggregation and precipitation were clearly observed even immediately after preparation.

[0143] Method for producing printed matter by ultraviolet irradiation The obtained ink composition was applied to a 100 μm thick PET film using a bar coater (RDS12) (film thickness after drying: 10 μm), and cured by ultraviolet irradiation (inverter type conveyor device ECS-4011GX, metahalide lamp M04-L41, manufactured by iGraphics Co., Ltd.) to produce a printed material.

[0144] (Curing evaluation) When a printed matter was produced by the above method, the cumulative amount of light until the ink composition was completely cured (to a non-sticky state) was measured, and the curability was evaluated. ◎: 1000mJ / cm 2 Completely hardened ○: 1000~2000mJ / cm 2 Completely hardened △: 2000~5000mJ / cm 2 Completely hardened ×: 5000mJ / cm until complete curing 2 More than necessary

[0145] (Surface drying evaluation) The printed matter produced using the above method was left to stand for 5 minutes in an environment at room temperature of 23°C and relative humidity of 50%, and then high-quality paper was placed on top of the printed surface. A load of 1 kg / cm2 was applied for 1 minute to evaluate the degree of ink transfer to the paper. ◎: The ink was dry and not transferred to the paper at all. ○: The ink dried and there was a small amount of transfer to the paper. △: The ink is almost dry and has been transferred to the paper. ×: The ink hardly dried and there was a lot of transfer onto the paper.

[0146] (Adhesion evaluation) The obtained ink composition was applied to various substrates and irradiated with ultraviolet light (apparatus: Inverter type conveyor device ECS-4011GX manufactured by Eye Graphics, metal halide lamp: M04-L41 manufactured by Eye Graphics, ultraviolet irradiance: 700 mW / cm 2 , Accumulated light intensity: 1000mJ / cm 2The resulting cured film was subjected to a checkerboard test to create 100 1 mm squares, and cellophane tape was attached to the squares. The tape was then peeled off in one go, and the number of squares with the cured film remaining on the substrate was counted and evaluated. ◎: 100 remaining squares 〇: Remaining squares are 90 or more but less than 100 △: Remaining squares are between 50 and 90 ×: Less than 50 squares remaining

[0147] (Inkjet printing and printability evaluation) The ink composition prepared above was filled into a commercially available inkjet printer (LuxelJet U V350GTW manufactured by Fujifilm Corporation), and a solid image was printed on coated paper. The printability of the ink was evaluated by the following method.

[0148] (Evaluation of ejection stability) The printing condition of the resulting prints was evaluated visually. ◎: No missing nozzles and good printing 〇: Slight nozzle missing △: Nozzles missing over a wide area ×: Non-ejection occurs

[0149] (Clarity evaluation) The image clarity of the prints obtained from the ink compositions containing the pigment was visually observed. ◎: No ink bleeding was observed and the image was clear. ○: There was almost no ink bleeding and the image was good △: Some ink bleeding was observed ×: Significant ink bleeding was observed

[0150] (Yellowing resistance evaluation) The resulting clear ink composition was applied to a substrate (#125-E20) using a bar coater (RDS12) to a film thickness of 10 μm, and cured using a metal halide lamp in the same manner as above. The hue of the resulting coating was measured using a Spcetrolino (manufactured by GretagMacbeth) and the coating was left in a thermostatic chamber maintained at 60°C for one week. The hue of the coating was then measured again, and yellowing resistance was evaluated based on the change in hue value before and after heating (ΔE = hue after heating - hue before heating). ◎:0<=ΔE<=0.2 ○: 0.2<ΔE<=0.5 △:0.5<ΔE<=1.0 ×:1.0<ΔE

[0151] [Table 12]

[0152] Examples 114 to 122 and Comparative Examples 34 and 35 The polymer obtained in Table 1, the polymerizable composition obtained in Table 2, and other ingredients were weighed out according to the proportions (solids content equivalent) shown in Table 13, and mixed uniformly at room temperature to prepare an ink composition for three-dimensional modeling. The cure shrinkage of the ink composition for three-dimensional modeling, as well as the strength, heat resistance, water resistance, and modeling accuracy of the cured product of the ink composition for three-dimensional modeling, were measured using the methods described below. The evaluation results are shown in Table 13.

[0153] (Cure shrinkage resistance evaluation) The cure shrinkage rate was determined in accordance with JIS K5600 2-4 from the change in density of the ink composition for three-dimensional modeling before and after curing, as shown in the following calculation formula (1). The density of the ink composition for three-dimensional modeling before and after curing was measured in accordance with JIS K7112 using an electronic hydrometer (MDS-300 manufactured by Alpha Mirage Co., Ltd.). The cured product was prepared in the same manner as the test piece for the tensile test. The following evaluations were made from the obtained cure shrinkage rate. (Cure shrinkage rate) = (Ds - Dl) / Dl x 100 Calculation formula (1) (In the formula, Ds is the density of the ink composition for three-dimensional modeling after curing, and Dl is the density of the ink composition for three-dimensional modeling before curing.) ◎: Curing shrinkage rate less than 6% ○: Curing shrinkage rate 6% or more and less than 7% △: Curing shrinkage rate 7% or more and less than 8% ×: Curing shrinkage rate 8% or more

[0154] (Strength evaluation) A 75 μm thick heavy release PET film (Toyobo Co., Ltd., polyester film E7001) was placed in close contact with a horizontally placed glass plate, and a 1 mm thick spacer punched into a No. 2 dumbbell shape conforming to JIS K6251 was placed inside the spacer. The ink composition for three-dimensional modeling obtained in each example and comparative example was then filled inside the spacer. A 50 μm thick light release PET film (Toyobo Co., Ltd., polyester film E7002) was then placed on top of the spacer, and ultraviolet light was irradiated from both sides (device: Eye Graphics, inverter type conveyor device ECS-4011GX; metal halide lamp: Eye Graphics, M04-L41; ultraviolet irradiance: 200 mW / cm). 2 , cumulative light intensity 1000mJ / cm 2 ) to cure the ink composition for three-dimensional modeling. The release PET films on both sides were then removed to obtain test pieces of the cured product for the examples and the comparative examples. According to JIS K7161, the tensile strength was measured using a bench-top precision universal testing machine (Shimadzu Corporation, Autograph AGS-X) at a temperature of 25°C, with a tensile speed of 10 mm / min and a chuck distance of 50 mm, and the strength was evaluated according to the following criteria. ◎: Tensile strength 40 MPa or more ○: Tensile strength 30 MPa or more and less than 40 MPa △: Tensile strength 20MPa or more and less than 30MPa ×: Tensile strength less than 20 MPa

[0155] (Heat resistance evaluation) Cured products were prepared in the same manner as the test pieces for the tensile tests, and the glass transition temperatures (Tg) of the cured products were measured using a differential scanning calorimeter (DSC-60plus, manufactured by Shimadzu Corporation). The heat resistance was evaluated as follows based on the measured glass transition temperatures (Tg) of the cured products. ◎: Cured product Tg 80℃ or more ○: Tg of cured product is 40℃ or higher and less than 80℃ ×: Tg of cured product less than 40°C

[0156] (Water resistance evaluation) A 75 μm thick heavy-release PET film (Toyobo Co., Ltd., Polyester Film E7001) was placed on a horizontally placed glass plate, and a 10 mm thick spacer with an internal dimension of 10 cm x 1 cm was placed. The ink composition for three-dimensional modeling obtained in each Example and Comparative Example was filled to a thickness of 1 mm inside the spacer, and the surface was smoothed by incubating at 60°C for 30 seconds. After that, ultraviolet light was irradiated (apparatus: Eye Graphics, inverter type conveyor device ECS-4011GX; metal halide lamp: Eye Graphics, M04-L41; ultraviolet irradiance: 200 mW / cm 2 ) and curing the ink composition for three-dimensional modeling to obtain a cured product measuring 10 cm in length, 1 cm in width, and 1 mm in thickness. The weight of the obtained cured product was measured immediately after production, and then it was immersed in a beaker containing 100 ml of water. After one day, the weight after immersion was measured. The weight before immersion and the weight after immersion were substituted into the following equation to measure the water absorption rate, and water resistance was evaluated according to the following criteria. ◎: Water absorption rate is less than 2% ○: Water absorption rate is 2% or more and less than 2.5% △: Water absorption rate is 2.5% or more and less than 3% ×: Water absorption rate is 3% or more

[0157] (Modeling accuracy evaluation) A 75 μm thick heavy-release PET film (Toyobo Co., Ltd., Polyester Film E7001) was attached to a horizontally placed glass plate, and a 10 mm thick spacer with an internal dimension of 10 × 10 mm was placed. The spacer was filled with the ink composition for three-dimensional modeling obtained in each Example and Comparative Example to a thickness of 1 mm. The surface was then smoothed by incubating at 60°C for 30 seconds, and then irradiated with ultraviolet light (apparatus: Eye Graphics, inverter type conveyor device ECS-4011GX; metal halide lamp: Eye Graphics, M04-L41; ultraviolet irradiance: 200 mW / cm). 2 ) and the ink composition for three-dimensional modeling was cured. Thereafter, the ink composition for three-dimensional modeling was filled to a thickness of 1 mm, and the curing process was repeated 10 times to obtain a cured product measuring 10 x 10 x 10 mm. The height of the obtained cured product was measured. In addition, the side surface of the obtained cured product was visually observed. These results were combined and the modeling accuracy was evaluated according to the following criteria. ◎: Height is less than 10mm ± 0.1mm and there are no irregularities on the side. ○: Height is 10mm ±0.1mm or more but less than ±0.2mm, or there is very slight unevenness on the side. △: Height 10mm ±0.2mm or more but less than ±0.3mm, or slight unevenness on the side. ×: Height is 10 mm ± 0.3 mm or more, or there are obvious irregularities on the side.

[0158] [Table 13]

[0159] As shown in the evaluation results of the above-mentioned examples and comparative examples, polymerizable compositions containing N-substituted (meth)acrylamide (A) having a specific structure according to the present invention have high transparency and good curability due to the well-balanced amphiphilicity of A, and also have excellent wettability with a wide range of substrates, from low to high polarity, including organic substrates, inorganic substrates, and organic-inorganic hybrid substrates. Furthermore, their polymers or cured products have excellent water resistance due to the influence of the hydrophobic substituents possessed by A. Pressure-sensitive adhesive compositions containing the polymerizable composition and / or polymers thereof, etc., and laminates of pressure-sensitive adhesive layers comprising the pressure-sensitive adhesive composition and various substrates, exhibit adhesion and strength to various substrates and have high transparency, contamination resistance, yellowing resistance, and durability. Adhesive compositions containing the polymerizable composition and / or polymers thereof, etc., have high adhesion, impact resistance, and water resistance to various substrates, and can be used as adhesive compositions for homogeneous or heterogeneous materials. Cosmetic compositions containing the polymerizable composition and / or its polymers can be used as hair cosmetics that are moisture-resistant, smooth, and resistant to stickiness, have a good texture, and are stable over time, or as oil-in-water emulsion cosmetic compositions that exhibit no skin irritation and have excellent emulsion stability, a pleasant feel when used, and are stable over time. Coating compositions containing the polymerizable composition and / or its polymers have high wettability and adhesion to various substrates and exhibit high surface hardness and water resistance upon curing. It is clear that ink compositions have high adhesion to various substrates and are excellent in printing properties such as pigment dispersibility, surface drying, ejection stability, and clarity, as well as high curing properties and yellowing resistance. Furthermore, ink compositions for three-dimensional modeling containing the polymerizable composition and / or its polymers can be used to accurately model three-dimensional objects that have high strength, heat resistance, and water resistance. On the other hand, it is clear that various molded articles obtained using a polymerizable composition and / or a polymer thereof that does not contain an N-substituted (meth)acrylamide (A), such as a pressure-sensitive adhesive composition, an adhesive composition, a cosmetic composition, a coating composition, an ink composition, and an ink composition for three-dimensional modeling, are inferior in effect to the various molded articles obtained from the above-mentioned polymerizable composition containing A and / or a polymer thereof. [Industrial Applicability]

[0160] As described above, the polymerizable composition of the present invention, containing a specific N-substituted (meth)acrylamide (A), has high transparency and good curability, while exhibiting excellent wettability to various substrates with a wide range of polarities, from low to high. Furthermore, the resulting polymer exhibits excellent water resistance. Therefore, the polymerizable composition and / or its polymer can be used as a pressure-sensitive adhesive composition that can be polymerized and cured by active energy rays and / or heat, and can be used in pressure-sensitive adhesives and pressure-sensitive adhesive-related products in a wide range of fields, including industrial, medical, and household applications. The pressure-sensitive adhesive composition exhibits excellent adhesion to various substrates with a wide range of polarities. For example, a polyolefin pressure-sensitive adhesive sheet or a polyimide pressure-sensitive adhesive sheet can be obtained by forming a pressure-sensitive adhesive layer on a film or sheet-like substrate made of resins such as polyolefins (e.g., polyethylene and polypropylene), polycarbonate, acrylonitrile-butadiene-styrene copolymer, polyimide, and polymethyl methacrylate. Furthermore, when the pressure-sensitive adhesive layer is formed on a glass or metal substrate, a glass pressure-sensitive adhesive sheet or a metal pressure-sensitive adhesive sheet can be obtained. Furthermore, it is possible to easily obtain pressure-sensitive adhesive sheets for electronic materials, which include a substrate and an adhesive layer for use in electronic devices; pressure-sensitive adhesive sheets for optical components, which include a substrate and an adhesive layer for use in optical components; and pressure-sensitive adhesive sheets for automobiles, which include a substrate and an adhesive layer for use in automobiles. The adhesive composition comprising the pressure-sensitive adhesive composition of the present invention and a crosslinker is highly effective for bonding both homogeneous materials and various dissimilar materials, from plastics to metals, and can be widely used in electronic materials, optical components, semiconductors, solar cells, etc. The adhesive composition can also be used for cosmetics that have excellent moisture resistance and emulsion stability and a pleasant feel when used; coating agents that have excellent adhesion to various substrates and can provide coating layers with high surface hardness and water resistance; inks that have high adhesion to various substrates, excellent printing properties such as pigment dispersibility, surface drying properties, ejection stability, and clarity, and have high curability and yellowing resistance; and three-dimensional modeling inks that have excellent cure shrinkage resistance and can accurately model three-dimensional objects with high strength, heat resistance, and water resistance.

Claims

1. A coating composition containing a polymerizable composition containing any one of N-substituted (meth)acrylamide (A) represented by general formula [1], 2-ethylhexyl(meth)acrylamide, and N,N-di-(2-ethylhexyl)acrylamide, or a polymer obtained by polymerizing the polymerizable composition with active energy rays and / or heat. 【Chemistry 1】 (In the formula, R １ represents a hydrogen atom or a methyl group, and R ２ represents a substituent having one or more structures selected from a linear saturated chain structure having 6 or more carbon atoms, a linear unsaturated structure, and a cyclic saturated structure; R ３ represents a hydrogen atom, a chain hydrocarbon group having one or more carbon atoms, or a cyclic hydrocarbon group having three or more carbon atoms.

2. N-substituted (meth)acrylamide (A) includes n-hexyl(meth)acrylamide, n-heptyl(meth)acrylamide, n-octyl(meth)acrylamide, n-decyl(meth)acrylamide, n-undecyl(meth)acrylamide, n-dodecyl(meth)acrylamide, n-tridecyl(meth)acrylamide, n-trimethyldecyl(meth)acrylamide, n-tetradecyl(meth)acrylamide, n-hexadecyl(meth)acrylamide, n-stearyl(meth)acrylamide, n-methyldecyl ... N-cyclohexyl(meth)acrylamide, N-eicosyl(meth)acrylamide, N-docosyl(meth)acrylamide, N-tetracosyl(meth)acrylamide, N-cyclohexyl(meth)acrylamide, N,N-dicyclohexyl(meth)acrylamide, N-cyclohexyl-N-methyl(meth)acrylamide, N-cyclohexyl-N-ethyl(meth)acrylamide, N-cyclohexyl-N-propyl(meth)acrylamide, N-cyclohexyl-N-butyl(meth)acrylamide Acrylamide, N-cyclohexyl-N-pentyl(meth)acrylamide, N-cyclohexyl-N-hexyl(meth)acrylamide, N-(meth)acryloylhexamethyleneimine, N-(meth)acryloyl-2-methylhexamethyleneimine, N-(meth)acryloyl-3-methylhexamethyleneimine, N-(meth)acryloyl-4-methylhexamethyleneimine, N-(meth)acryloyl-2-ethylhexamethyleneimine, N-(meth)acryloyl- 3-ethylhexamethyleneimine, N-(meth)acryloyl-4-ethylhexamethyleneimine, N-(meth)acryloyl-3-propylhexamethyleneimine, N-(meth)acryloyl-4-propylhexamethyleneimine, N-(meth)acryloyl-3-isopropylhexamethyleneimine, N-(meth)acryloyl-4-isopropylhexamethyleneimine, N-(meth)acryloyl-3,5-dimethylhexamethyleneimine, N-(meth)acryloyl-4,4-dimethylhexamethyleneimine, N-(meth)acryloylheptamethyleneimine, N-(meth)acryloyloctamethyleneimine, N-(meth)acryloyldecamethyleneimine, hexenyl(meth)acrylamide, heptenyl(meth)acrylamide, octenyl(meth)acrylamide, nonenyl(meth)acrylamide, decenyl(meth)acrylamide, undecenyl(meth)acrylamide, dodecenyl(meth)acrylamide, tetradecenyl(meth)acrylamide, hexadecenyl(meth)acrylamide, oleyl(meth)acrylamide, icosenyl(meth)acrylamide, docosenyl(meth)acrylamide, tetracosenyl(meth)acrylamide, octadecadienyl(meth)acrylamide, icosadienyl(meth)acrylamide, docosadienyl(meth)acrylamide, The coating agent composition according to claim 1, comprising one or more compounds selected from the group consisting of tetracosadienyl (meth)acrylamide, octadecatrienyl (meth)acrylamide, icosatrienyl (meth)acrylamide, docosatrienyl (meth)acrylamide, tetracosatrienyl (meth)acrylamide, octadecatetraenyl (meth)acrylamide, icosatetraenyl (meth)acrylamide, docosatetraenyl (meth)acrylamide, tetracosatetraenyl (meth)acrylamide, octadecapentaenyl (meth)acrylamide, icosapentaenyl (meth)acrylamide, docosapentaenyl (meth)acrylamide, tetracosapentaenyl (meth)acrylamide, docosahexaenyl (meth)acrylamide, and tetracosahexaenyl (meth)acrylamide.

3. 3. The coating composition according to claim 1, wherein the saturated water absorption of the polymer or cured product of the polymerizable composition is 10% or less.

4. 4. The coating composition according to claim 1, wherein the content of the N-substituted (meth)acrylamide (A), 2-ethylhexyl(meth)acrylamide, or N,N-di-(2-ethylhexyl)acrylamide is 1% by weight or more based on the total weight of the polymerizable composition.

5. 5. The coating composition according to claim 1, further comprising one or more monofunctional monomers or monofunctional oligomers selected from the group consisting of monofunctional (meth)acrylates, monofunctional (meth)acrylamides (excluding N-substituted (meth)acrylamides (A)), styrene, vinyl group-containing monomers, allyl group-containing monomers, and maleimide group-containing monomers.

6. The monofunctional monomer is methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, hydroxyethyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, tridecyl (meth)acrylate, methoxyethyl ( (meth)acrylate, ethoxyethyl (meth)acrylate, propoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, methoxydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexa Ethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, cyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, bornyl (meth)acrylate, isobornyl (meth)acrylate, tetrahydrofurfuryl acrylate, 2-methyl-2-adamantyl (meth)acrylate, butyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, hydroxyhexyl (meth)acrylate, N-methyl (meth)acrylamide, N-ethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-butyl (meth)acrylamide, N-methoxymethyl (meth)acrylamide, N-ethoxymethyl (meth)acrylamide, N-methoxyethyl (meth)acrylamide,N-ethoxyethyl (meth)acrylamide, N-n-butoxymethyl (meth)acrylamide, N-isobutoxymethyl (meth)acrylamide, N-(2-hydroxyethyl)acrylamide, N-[3-(dimethylamino)]propylacrylamide, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, diacetone (meth)acrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, acrylonitrile , vinyl acetate, styrene, vinyloxazoline, N-(meth)acryloylpiperidine, N-(meth)acryloyl-2-methylpiperidine, N-(meth)acryloyl-3-methylpiperidine, N-(meth)acryloyl-4-methylpiperidine, N-(meth)acryloyl-2,6-dimethylpiperidine, N-(meth)acryloyl-3,5-dimethylpiperidine, N-(meth)acryloyl-3,3-dimethylpiperidine, N-(meth)acryloyl-4 ,4-dimethylpiperidine, N-(meth)acryloyl-2,2,6,6-tetramethylpiperidine, N-(meth)acryloyl-2-methyl-5-ethylpiperidine, N-(meth)acryloyl-4-methyl-4-ethylpiperidine, N-(meth)acryloyl-2-ethylpiperidine, N-(meth)acryloyl-3-ethylpiperidine, N-(meth)acryloyl-4-ethylpiperidine, N-(meth)acryloyl-2-propylpiperidine, N-(meth)acryloyl p) The coating agent composition according to claim 5, which contains one or more compounds selected from the group consisting of acryloyl-3-propylpiperidine, N-(meth)acryloyl-4-propylpiperidine, N-(meth)acryloyl-3-isopropylpiperidine, N-(meth)acryloyl-4-isopropylpiperidine, tert-octyl(meth)acrylamide, dopamine(meth)acrylamide, and 3-(meth)acrylamidophenylboronic acid.

7. The coating composition according to any one of claims 1 to 6, further comprising a crosslinking agent.

8. The coating agent composition according to any one of claims 1 to 7, further comprising one or more compounds selected from the group consisting of an isocyanate compound, an epoxy compound, an aziridine compound, a compound having a carboxyl group, and a compound having an oxazoline group.

9. The coating composition according to any one of claims 1 to 8, further comprising one or more compounds selected from the group consisting of polyfunctional monomers, polyfunctional oligomers, and polymerizable polymers.

10. The coating composition according to any one of claims 1 to 9, further comprising one or more compounds selected from the group consisting of a polymerization initiator, a non-polymerizable oligomer, and a non-polymerizable polymer.

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