Polymerizable compounds, methods for producing polymerizable compounds, compositions for forming adhesive and tacky layers, and adhesive and tacky polymers.

Abstract

The present invention provides polymerizable compounds that, even without a catechol skeleton or pyrogallol skeleton, can impart or further enhance adhesiveness and tackiness, and can be used to prepare adhesive and tackiness-forming compositions and adhesive and tackiness polymers that can form adhesive layers with excellent adhesive and tackiness on various substrates. [Solution] The polymerizable compound is represented by the following general formula (1) and is useful as a material for preparing, for example, a composition for forming adhesive or tacky layers or an adhesive or tacky polymer. TIFF2026122770000020.tif41170 (In general formula (1), R represents a hydrogen atom or a methyl group)

Description

Technical Field

[0001] The present invention relates to a polymerizable compound, a method for producing the polymerizable compound, a composition for forming an adhesive or adhesive layer, and an adhesive or adhesive polymer.

Background Art

[0002] In recent years, compounds having a catechol skeleton or a pyrogallol skeleton in which a plurality of hydrogen atoms adjacent to a benzene ring are substituted with hydroxyl groups have been proposed as useful materials for adhesive applications and the like. Since the orientation of adjacent hydroxyl groups in the catechol skeleton or pyrogallol skeleton is fixed, it is advantageous in that it is easy to interact with the adherend surface, such as through hydrogen bonding.

[0003] For example, a curable resin composition containing a monomer such as dopamine acrylamide containing a catechol skeleton has been proposed (Patent Document 1). Also, acrylic monomers having a pyrogallol skeleton that can be used in adhesive compositions and adhesive tapes have been proposed (Patent Documents 2 and 3).

[0004] Furthermore, a mechanism has been proposed in which the hydroxyl groups in a highly reactive catechol skeleton are protected and deprotected during use to exhibit adhesiveness (Non-Patent Document 1). Also, it has been proposed to suppress oxidation and modification of the catechol skeleton by placing it in a pH buffer and a hydrophobic environment (Non-Patent Document 2).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Non-Patent Documents

[0007] However, the monomers proposed in Patent Documents 1 to 3 have unstable skeletons, such as the catechol skeleton and pyrogallol skeleton, which are easily modified and discolored by oxidation. Therefore, further improvements were needed for application in industrial uses that require high heat resistance and long-term stability.

[0008] Furthermore, the protective polymer proposed in Non-Patent Document 1 is relatively expensive because it needs to be manufactured using dopamine and O-nitrobenzyl groups. In addition, adhesive layers formed using deprotected polymers have the problem of being prone to degradation and discoloration because the exposed catechol skeleton remains.

[0009] Furthermore, the method proposed in Non-Patent Document 2 requires the use of expensive dopamine derivatives, making it difficult to apply to industrial uses. In addition, because the catechol skeleton remains intact, there was room for improvement in terms of heat resistance and long-term stability.

[0010] The present invention has been made in view of the problems of the prior art, and its objective is to provide a polymerizable compound that can prepare adhesive and tacky layer-forming compositions and adhesive and tacky polymers that can impart or further enhance adhesiveness and tackiness, even without having a catechol skeleton and a pyrogallol skeleton, and that can form adhesive layers with excellent adhesiveness and tackiness on various substrates, as well as a method for producing the same.

[0011] Furthermore, an object of the present invention is to provide an adhesive / tacky layer-forming composition and an adhesive / tacky polymer that can impart or further enhance adhesiveness and tackiness, even without having a catechol skeleton and a pyrogallol skeleton, and can form an adhesive layer with excellent adhesiveness and tackiness on various substrates. [Means for solving the problem]

[0012] As a result of diligent research by the inventors to solve the above problems, it was discovered that by introducing a polymerizable substituent to the amino group of cytidine having a cis-1,2-diol structure, it is possible to provide an adhesive / tacky layer-forming composition and an adhesive / tacky polymer that can form adhesive layers with excellent adhesion and tackiness on various substrates, even without having a catechol skeleton or pyrogallol skeleton.

[0013] In other words, the present invention provides the polymerizable compounds shown below. [1] A polymerizable compound represented by the following general formula (1).

[0014] TIFF2026122770000001.tif41170 (In the above general formula (1), R represents a hydrogen atom or a methyl group)

[0015] [2] The polymerizable compound according to claim 1, wherein the purity measured by HPLC is 80% or higher. [3] A polymerizable compound according to [1] or [2] above, used as a composition for forming adhesive or tacky layers or as a material for preparing an adhesive or tacky polymer.

[0016] Furthermore, the present invention provides a method for producing polymerizable compounds as shown below. [4] A method for producing a polymerizable compound according to any one of [1] to [3] above, comprising the step of reacting cytidine with 2-isocyanatoethyl (meth)acrylate.

[0017] Furthermore, the present invention provides the following adhesive and bonding layer-forming compositions. [5] An adhesive and tacky layer-forming composition containing a polymerizable compound represented by the following general formula (1).

[0018] TIFF2026122770000002.tif41170 (In the general formula (1), R represents a hydrogen atom or a methyl group)

[0019] [6] The adhesive and tacky layer-forming composition according to [5], further containing a polymerization initiator. [7] The adhesive and tacky layer-forming composition according to [5] or [6], wherein the content of the polymerizable compound is 0.1 to 10% by mass based on the solid content.

[0020] Further, according to the present invention, an adhesive and tacky polymer shown below is provided. [8] An adhesive and tacky polymer having a structural unit (i) derived from a first polymerizable compound represented by the following general formula (1).

[0021] TIFF2026122770000003.tif41170 (In the general formula (1), R represents a hydrogen atom or a methyl group)

[0022] [9] The adhesive and tacky polymer according to [8], wherein the content of the structural unit (i) is from 0.1 to 10% by mass.

Advantages of the Invention

[0023] According to the present invention, it is possible to provide a polymerizable compound capable of preparing an adhesive and tacky layer-forming composition or an adhesive and tacky polymer that can form an adhesive layer excellent in adhesiveness and tackiness on various substrates by imparting adhesiveness and tackiness or further enhancing adhesiveness and tackiness without having a catechol skeleton and a pyrogallol skeleton, and a method for producing the same.

[0024] Furthermore, according to the present invention, it is possible to provide an adhesive / tacky layer-forming composition and an adhesive / tacky polymer that can impart or further enhance adhesiveness and tackiness, and form an adhesive layer with excellent adhesiveness and tackiness on various substrates, even without having a catechol skeleton and a pyrogallol skeleton. [Modes for carrying out the invention]

[0025] <Polymerizable compound> The embodiments of the present invention will be described below, but the present invention is not limited to the embodiments described below. One embodiment of the polymerizable compound of the present invention is a compound useful as a material for preparing an adhesive / tacky layer forming composition or an adhesive / tacky polymer, represented by the following general formula (1). The details of the polymerizable compound of this embodiment will be described below.

[0026] TIFF2026122770000004.tif41170 (In the above general formula (1), R represents a hydrogen atom or a methyl group)

[0027] In general formula (1), R is a hydrogen atom or a methyl group. By appropriately selecting R according to the purpose and application, polymerizable compounds can be produced that can form adhesive and tacky layer-forming compositions and adhesive and tacky polymers on various substrates, resulting in adhesive and tacky layers with superior adhesion and tackiness.

[0028] The polymerizable compound of this embodiment preferably has a purity of 80% or higher as measured by HPLC (high-performance liquid chromatography), more preferably 90% or higher, even more preferably 95% or higher, particularly preferably 98% or higher, and most preferably 99% or higher. By using such a high-purity polymerizable compound, it is possible to prepare adhesive and tack-forming compositions that can form adhesive layers with superior adhesion and tackiness.

[0029] The purity of the polymerizable compound in this embodiment is measured by HPLC. The purity of the polymerizable compound is expressed as the ratio (percentage) of the area of ​​the absorption peak corresponding to the polymerizable compound represented by general formula (1) to the total peak area of ​​the chromatogram, which records the change in absorption intensity of light with a wavelength of 294 nm (ultraviolet (UV)), measured by HPLC. The total peak area of ​​the chromatogram means the sum of the areas of the absorption peaks derived from each component separated by HPLC. However, absorption peaks derived from the dilution solvent and bubbles of the polymerizable compound; absorption peaks derived from impurities contained in the dilution solvent and eluent; absorption peaks associated with background changes due to the gradient of the eluent composition; absorption peaks with an area ratio of 0.1% or less; and background peaks obtained when only the dilution solvent is measured are not included in the total peak area of ​​the chromatogram. The HPLC conditions can be as follows. Analytical equipment: LCMS system consisting of LC-30AD, SPD-M20A, and LCMS-8050 (manufactured by Shimadzu Corporation) Eluent: Acetonitrile-3% acetic acid aqueous solution (1:19 → 17:3 (v / v), gradient over 40 minutes) Flow rate: 0.2mL / min Column: L-column2 ODS 2μm (3.0×100mm) (manufactured by Chemicals Evaluation and Research Institute) Column temperature: 40℃ Sample: 2.0 μL of approximately 100 ppm THF solution Detection wavelength: 294nm

[0030] <Method for producing polymerizable compounds> Next, a method for producing polymerizable compounds according to the present invention will be described. One embodiment of the method for producing polymerizable compounds according to the present invention is the method for producing polymerizable compounds described above, comprising the step of reacting cytidine with 2-isocyanatoethyl (meth)acrylate (hereinafter also referred to as "step (1)").

[0031] In step (1), from the viewpoint of the solubility and reactivity of cytidine, the reaction temperature is preferably 20 to 150°C, more preferably 40 to 130°C, and particularly preferably 60 to 110°C. After the completion of step (1), the target polymerizable compound can be obtained by separation and purification according to conventional methods.

[0032] In step (1), cytidine and 2-isocyanatoethyl (meth)acrylate can be reacted in the presence of a reaction solvent. A general organic solvent can be used as the reaction solvent. Examples of organic solvents include ether-based solvents such as tetrahydrofuran, 1,2-dimethoxyethane, and 1,4-dioxane; amide-based solvents such as dimethylformamide and N-methylpyrrolidone; and the like.

[0033] In step (1), cytidine may be reacted with 2-isocyanatoethyl (meth)acrylate using a catalyst. Suitable catalysts include Lewis acid catalysts such as dibutylsusulauric acid, tetra-n-butyl titanate, tetrakisacetylacetonatozirconium, zinc 2-ethylhexanoate, and bismuth 2-ethylhexanoate; Brønsted acid catalysts such as hydrogen halides, phosphoric acid, sulfuric acid, nitric acid, sulfonic acid, and carboxylic acid; compounds capable of generating Brønsted acids such as acetyl chloride, acetyl bromide, acetyl iodide, dimethylcarbamoyl chloride, acrylate chloride, and methacrylate chloride; and Brønsted bases such as triethylamine, diisopropylethylamine, pyridine, and potassium t-butoxide.

[0034] The isocyanate group (-NCO) of 2-isocyanatoethyl (meth)acrylate preferentially reacts with the amino group (-NH2) of cytidine, but also reacts with some hydroxyl groups (-OH) to produce by-reactants. These by-reactants are then present as impurities in the resulting polymerizable compound. Examples of by-reactants (impurities) include compounds represented by the following general formula (2).

[0035] TIFF2026122770000005.tif38170 (In the above general formula (2), R1 to R4 each independently represent a hydrogen atom or a group represented by the following general formula (3), and if R1 is a group represented by the following general formula (3), then not all of R2 to R4 will be hydrogen atoms.)

[0036] TIFF2026122770000006.tif37170 (In the above general formula (3), R represents a hydrogen atom or a methyl group, and "*" indicates a bond position.)

[0037] Furthermore, 2-isocyanatoethyl (meth)acrylate may react with trace amounts of water to produce a by-reaction product represented by the following general formula (4). The resulting by-reaction product will be present as an impurity in the resulting polymerizable compound. In other words, the polymerizable compound of this embodiment may contain the compound represented by general formula (2) or the compound represented by the following general formula (4) as an impurity.

[0038] TIFF2026122770000007.tif23170 (In the above general formula (4), R represents a hydrogen atom or a methyl group)

[0039] <Composition for forming adhesive / adhesive layer> By using the polymerizable compounds described above, adhesive and adhesive layer-forming compositions can be prepared that can form adhesive or adhesive layers on various substrates. That is, one embodiment of the adhesive and adhesive layer-forming composition of the present invention is a composition containing a polymerizable compound represented by the following general formula (1). The details of the adhesive and adhesive layer-forming composition of this embodiment will be described below.

[0040] TIFF2026122770000008.tif41170 (In the above general formula (1), R represents a hydrogen atom or a methyl group)

[0041] In the composition for forming adhesive and tack layers, the content of polymerizable compounds is preferably 0.1 to 20% by mass, more preferably 0.1 to 10% by mass, even more preferably 0.2 to 10% by mass, and particularly preferably 0.5 to 5% by mass, based on the solid content of the composition. By using such a composition, an adhesive layer with excellent adhesion and tackiness can be formed.

[0042] The composition for forming adhesive and tack layers may further contain other polymerizable compounds besides the polymerizable compound represented by general formula (1). As the other polymerizable compounds, conventionally known compounds with radical polymerizability that constitute typical adhesive and tack polymers can be used.

[0043] Compounds with radical polymerization properties (so-called monomers) include acrylic acid, methacrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, 2-methylpropane (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tetradecyl (meth)acrylate, octadecyl Examples of aliphatic, alicyclic, and aromatic alkyl (meth)acrylates include methyl(meth)acrylate, behenyl(meth)acrylate, isostearyl(meth)acrylate, cyclohexyl(meth)acrylate, t-butylcyclohexylmethyl(meth)acrylate, isobolonyl(meth)acrylate, trimethylcyclohexyl(meth)acrylate, cyclodecyl(meth)acrylate, cyclodecylmethyl(meth)acrylate, benzyl(meth)acrylate, t-butylbenzotriazolephenylethyl(meth)acrylate, phenyl(meth)acrylate, naphthyl(meth)acrylate, and allyl(meth)acrylate.

[0044] Furthermore, compounds (monomers) that exhibit radical polymerization include hydroxyl group-containing (meth)acrylic acid monomers such as hydroxyethyl (meth)acrylamide, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polyethylene glycol-propylene glycol mono(meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 2-hydroxybutyl (meth)acrylate; (meth)acrylic acid monomers having glycol groups; (polyalkylene) glycol monoalkyl, alkylene, alkyne ether, and ester mono(meth)acrylates; (meth)acrylic acid monomers having acid groups (carboxyl group, sulfonic acid, phosphoric acid) including acrylic acid and acrylic acid dimers; (meth)acrylic acid monomers containing oxygen atoms; (meth)acrylic acid monomers having amino groups; and (meth)acrylic acid monomers containing nitrogen atoms. Nomers; gallic acid (2-(meth)acryloyloxyethyl), gallic acid (3-(meth)acryloyloxypropyl), gallic acid (4-(meth)acryloyloxybutyl), gallic acid (5-(meth)acryloyloxypentyl), gallic acid (6-(meth)acryloyloxyhexyl), gallic acid (2-(2-(meth)acryloyloxyethylaminocarbonyloxy)ethyl), gallic acid (3-(2-(meth)acryloyloxyethylaminocarbonyloxy)propyl), gallic acid (4-(2-(meth)acryloyl Mono(meth)acrylates having three or more hydroxyl groups, such as (royloxyethylaminocarbonyloxy)butyl), gallic acid (5-(2-(meth)acryloyloxyethylaminocarbonyloxy)pentyl), and gallic acid (6-(2-(meth)acryloyloxyethylaminocarbonyloxy)hexyl); (meth)acrylates containing halogen atoms; (meth)acrylic acid monomers containing silicon atoms; (meth)acrylic acid monomers having ultraviolet absorbing groups; α-hydroxyl group methyl-substituted acrylates;Examples include (meth)acrylates having two or more polymerizable substituents, such as N,N'-bis(2-(meth)acryloyloxyethyl)urea, 1-(2-(meth)acryloyloxyethylaminocarbonyloxy)-2-(meth)acryloyloxyethane, 1-(2-(meth)acryloyloxyethylaminocarbonyloxy)-3-(meth)acryloyloxypropane, 1-(2-(meth)acryloyloxyethylaminocarbonyloxy)-4-(meth)acryloyloxybutane, 1-(2-(meth)acryloyloxyethylaminocarbonyloxy)-5-(meth)acryloyloxypentane, and 1-(2-(meth)acryloyloxyethylaminocarbonyloxy)-6-(meth)acryloyloxyhexane.

[0045] Furthermore, examples of compounds (monomers) having radical polymerizability include (meth)acrylic acid monomers having two or more addition polymerizable groups, such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and (meth)acrylic acid esters of polyalkylene glycol adducts of trimethylolpropane; urethane acrylates, oligomers (urethane oligomers having (meth)acrylic groups); and the like.

[0046] By appropriately incorporating these compounds having radical polymerizability, an adhesive and tack layer-forming composition with physical properties suitable for the intended use can be obtained. The content of the compounds having radical polymerizability can be appropriately set according to the purpose and is not particularly limited. The content of the compounds having radical polymerizability is preferably 5 to 90% by mass, more preferably 10 to 80% by mass, even more preferably 15 to 70% by mass, and particularly preferably 20 to 60% by mass, based on the solid content in the adhesive and tack layer-forming composition.

[0047] The adhesive and tack-forming composition may further contain common polymerizable compounds such as vinyl compounds like styrene and vinyl acetate.

[0048] The adhesive and tack-forming composition may further contain a polymerization initiator. Photopolymerization initiators and thermal polymerization initiators can be used. Examples of photopolymerization initiators include acylphosphine oxides such as diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide; acetophenones such as 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,2-dimethoxy-2-phenylacetophenone, and diethoxyacetophenone; ketals such as benzyldimethylketal; benzoins such as benzoin and benzoin methyl ether; benzophenones such as benzophenone, benzoylbenzoic acid, and hydroxybenzophenone; other halogenated ketones, and acylphosphanates.

[0049] As thermal polymerization initiators, azo compounds and organic peroxides can be used. Examples of azo compounds include azobisisobutyronitrile, 1,1'-azobis(cyclohexanecarbonile), and 2,2'-azobis(2-methylpropanoic acid)dimethyl. Examples of organic peroxides include hydroperoxide compounds, dialkylperoxide compounds, peroxyester compounds, diacylperoxide compounds, ketoneperoxide compounds, peroxyketal compounds, and peroxydicarbonate compounds.

[0050] By further incorporating a solvent, the composition for forming adhesive and tack layers can be made into a paint with appropriate coating properties (applicability). Water and various organic solvents can be used as the solvent.

[0051] The adhesive and bonding layer-forming composition may contain other additives. Examples of other additives include silane coupling agents, thixotropic agents, blocking inhibitors, leveling agents, defoamers, antioxidants, thermoplastic resins, antistatic agents, waxes, heat stabilizers, crystallization accelerators, crystallization inhibitors, flame retardants, ultraviolet absorbers, antibacterial agents, antiviral agents, and deodorants.

[0052] Adhesive and tack-forming compositions can be manufactured by appropriately mixing polymerizable compounds, other polymerizable compounds, polymerization initiators, solvents, and other additives.

[0053] Adhesive and adhesive layers can be formed by applying an adhesive / adhesive layer-forming composition onto a substrate and curing the resulting coating layer. Methods for applying the adhesive / adhesive layer-forming composition onto a substrate include roll coating, gravure coating, comma coating, knife coating, and die coating.

[0054] When a photopolymerization initiator is used, a method can be employed in which the coating layer (composition for forming adhesive / tacky layers) is cured by irradiating the coating layer with active energy rays at a predetermined light intensity using an irradiation device that emits active energy rays such as visible light, ultraviolet light, and electron beams. Examples of irradiation devices include xenon lamps, xenon-mercury lamps, metal halide lamps, high-pressure mercury lamps, low-pressure mercury lamps, and fusion lamps. On the other hand, when a thermal polymerization initiator is used, a method can be employed in which the coating layer is heated to 50 to 250°C, for example, using a high-temperature furnace.

[0055] <Adhesive / adhesive polymer> One embodiment of the adhesive polymer of the present invention is a polymer having a constituent unit (i) derived from a polymerizable compound represented by the following general formula (1). Because the adhesive polymer of this embodiment contains a constituent unit (i) derived from a compound represented by the following general formula (1), it is possible to form adhesive layers and tacky layers with excellent adhesion and tackiness on various substrates. Furthermore, by using the adhesive polymer of this embodiment, it is possible to form adhesive layers and tacky layers with excellent adhesion on various substrates.

[0056] TIFF2026122770000009.tif41170 (In the above general formula (1), R represents a hydrogen atom or a methyl group)

[0057] The content of constituent unit (i) in the adhesive polymer may be set appropriately depending on the purpose. Specifically, the content of constituent unit (i) is preferably 0.1 to 10% by mass, more preferably 0.2 to 5% by mass, even more preferably 0.3 to 3% by mass, particularly preferably 0.5 to 2% by mass, and most preferably 0.8 to 1.5% by mass, based on the total adhesive polymer.

[0058] The adhesive polymer may further contain structural units other than structural unit (i). These other structural units can be formed using conventionally known polymerizable monomers or resins that constitute ordinary polymers having adhesive properties.

[0059] <Various products> By using the adhesive / tack layer forming composition or adhesive / tack polymer of this embodiment, products such as adhesive sheets can be formed. The adhesive sheet comprises a sheet-like support and an adhesive layer formed from the adhesive / tack layer forming composition or adhesive / tack polymer provided on one or both sides of the support. Examples of the support include resin films, laminate films containing resin films, paper, woven fabrics, and nonwoven fabrics. Examples of resin film materials include polyesters such as polyethylene terephthalate (PET) and polybutylene terephthalate (PBT), polyethylene, polypropylene, and polycarbonate. A release film may be laminated on the surface of the adhesive layer to protect it.

[0060] Furthermore, by using adhesive / tack layer forming compositions or adhesive / tack polymers, various laminates useful as optical films and the like can be formed. The laminate is formed by laminating a first substrate and a second substrate via an adhesive layer or tack layer formed by the aforementioned adhesive / tack layer forming compositions or adhesive / tack polymers. The first substrate and the second substrate may be made of the same material or different materials.

[0061] The materials used for the substrates (first substrate and second substrate) include inorganic materials such as glass, hydroxyapatite, titanium oxide, zinc oxide, iron oxide, and indium tin oxide (ITO); metallic materials such as aluminum (Al), copper (Cu), iron (Fe), gold (Au), platinum (Pt), silver (Ag), zinc (Zn), tin (Sn), titanium (Ti), and their alloys; and polypropylene (PP), polyethylene (PE), polytetrafluoroethylene (PTFE), polyimide (PI), and polycarbonate (PC). Examples of organic materials include polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polymethyl methacrylate (PMMA), polyphenylene sulfide (PPS), polyphenylene ether (modified PPE), triacetylcellulose (TAC), cycloolefin polymer (COP), acrylonitrile-butadiene-styrene copolymer (ABS), fiber-reinforced plastic (FRP), and molybdenum-aluminum-molybdenum laminated structure (MAM). [Examples]

[0062] The present invention will be described in detail below based on examples, but the present invention is not limited to these examples. In the examples and comparative examples, "parts" and "%" are based on mass unless otherwise specified.

[0063] Cytidine and p-toluenesulfonic acid hydrate were purchased from Tokyo Chemical Industry Co., Ltd. 2-isocyanatoethyl acrylate and 2-isocyanatoethyl methacrylate were purchased from Resonaq Corporation.

[0064] <Production of polymerizable compounds> (Example 1) Six parts cytidine and 0.2 parts p-toluenesulfonic acid hydrate were added to 50 parts 1,2-dimethoxyethane and stirred, and 4.3 parts 2-isocyanatoethyl methacrylate were added. After reacting at 80°C for 6 hours, the mixture was filtered to separate the white solid. 50 parts of deionized water were added to the separated white solid and stirred, and the precipitate obtained by filtering was dried at 105°C to obtain 8.3 parts polymerizable compound 1. The content of the compound represented by the following formula (A) in polymerizable compound 1 (purity of polymerizable compound 1), measured by LC-MS (high-performance liquid chromatography-mass spectrometry), was 98%. 1 The results of the 1H-NMR measurement (chemical shift) are shown below. The conditions for measuring purity by LC-MS are also shown below. 1 H-NMR(DMSO-d6,400MHz):δ=9.99(s,1H),9.16(s,1H),8.27(d,J=7.3Hz,1H), 6.25(s,1H),6.12(s,1H),5.77(d,J=2.9Hz,1H),5.69(s,1H),5.47(s,1H),5. 15(s,1H),5.06(s,1H),4.17(t,J=5.3Hz,2H),3.96(s,2H),3.89(s,1H),3.72 (d,J=12.2Hz,1H),3.59(d,J=12.2Hz,1H),3.52(dt,J=5.3Hz,2H),1.90(s,3H)

[0065] [Conditions for measuring purity using LC-MS] Analytical equipment: LCMS system consisting of LC-30AD, SPD-M20A, and LCMS-8050 (manufactured by Shimadzu Corporation) Eluent: Acetonitrile-3% acetic acid aqueous solution (1:19 → 17:3 (v / v), gradient over 40 minutes) Flow rate: 0.2mL / min Column: L-column2 ODS 2μm (3.0×100mm) (manufactured by Chemicals Evaluation and Research Institute) Column temperature: 40℃ Sample: 1.0 μL of approximately 100 ppm DMF solution Detection wavelength: 294nm

[0066] TIFF2026122770000010.tif43170

[0067] (Example 2) Six parts cytidine and 0.2 parts p-toluenesulfonic acid hydrate were added to 50 parts 1,2-dimethoxyethane and stirred, and 3.9 parts 2-isocyanatoethyl acrylate were added. After reacting at 80°C for 6 hours, the mixture was filtered to separate the white solid. 50 parts of deionized water were added to the separated white solid and stirred, and the precipitate obtained by filtering was dried at 105°C to obtain 8.3 parts polymerizable compound 2. The content of the compound represented by the following formula (B) in polymerizable compound 2 (purity of polymerizable compound 2), measured by LC-MS, was 98%. 1 The results of the 1H-NMR measurement (chemical shift) are shown below. 1 H-NMR(DMSO-d6,400MHz):δ=9.97(s,1H),9.17(s,1H),8.27(d,J=7.3Hz,1H),6.39(dd,J=1 7.1,1.5Hz,1H),6.21(dd,J=17.6,10.2Hz,2H),5.97(dd,J=10.2,1.5Hz,1H),5.77(d,J=2.9 Hz,1H),5.46(s,1H),5.00-5.20(m,2H),4.19(t,J=5.4Hz,2H),3.97-3.93(m,2H),3.89-3. 86(m,1H),3.72(dd,J=12.2,2.4Hz,1H),3.58(dd,J=12.2,2.4Hz,1H),3.50(q,J=5.4Hz,2H)

[0068] TIFF2026122770000011.tif42170

[0069] (Comparative Example 1) Polymerizable compound 3 was synthesized according to the method described in Patent Document 2. The content of the compound represented by the following formula (C) in polymerizable compound 3 (purity of polymerizable compound 3) was 98%.

[0070] TIFF2026122770000012.tif34170

[0071] (Comparative Example 2) A commercially available compound represented by the following formula (D) was designated as polymerizable compound 4.

[0072] TIFF2026122770000013.tif21170

[0073] <Manufacturing of adhesive and adhesive layer-forming compositions> (Example 3) A composition for forming adhesive and tacky layers (paint) was obtained by mixing 50 parts of UV-curable urethane acrylate (UV-3700B) (product name "Shiko UV-3700B", manufactured by Mitsubishi Chemical Corporation, a urethane oligomer having (meth)acrylic groups), 5 parts of polymerization initiator (diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide (TPO)), 49 parts of acrylic monomer (dimethylacrylamide (DMAA)), and 11 parts of polymerizable compound.

[0074] (Examples 4-6, Comparative Examples 3 and 4, Reference Example 1) A composition (paint) for forming an adhesive / tacky layer was obtained in the same manner as in Example 3 described above, except that the formulation (unit: parts) was as shown in Table 1.

[0075] TIFF2026122770000014.tif62170

[0076] <Evaluation of compositions for adhesive and adhesive layer formation> (OCR evaluation (evaluation of adhesive strength)) The manufactured paint was applied to a glass plate to form a coating layer. A polyethylene terephthalate (PET) film was placed on the coating layer, which had formed an easy-adhesion surface, and laminated. The coating layer was then cured by UV irradiation. After being left for 6 days, the pieces were cut to obtain strip-shaped test pieces, and the peel strength was measured. The peel strength of the test piece obtained using the paint in Reference Example 1 was set to "100 (%)", and the adhesive strength of each test piece was evaluated relatively. The evaluation criteria are shown below. The evaluation results are shown in Table 2. ◎: 150% or more ○: 100% or more, less than 150% △: 50% or more but less than 100% ×: Less than 50%

[0077] TIFF2026122770000015.tif69170

[0078] (Evaluation of heat resistance) The manufactured paint was applied to a glass plate to form a coating layer. The glass plate was then placed on a polyethylene terephthalate (PET) film and laminated. The coating layer was then cured by UV irradiation. After 6 days, the pieces were cut to obtain strip-shaped test specimens, which were then heated at 105°C for 16 hours to evaluate their heat resistance. The color of the test specimen obtained using the paint from Reference Example 1 was set as the "standard," and the color of each test specimen was visually evaluated relative to the standard. The evaluation criteria are shown below. The evaluation results are shown in Table 3. ◎: No change in color whatsoever ○: Almost no change in color △: Slight variation in color. ×: Significant change in color.

[0079] TIFF2026122770000016.tif68170 [Industrial applicability]

[0080] The polymerizable compound of the present invention is useful as a material for preparing adhesive and tack-forming compositions that can form adhesive layers with excellent adhesion and tackiness between dissimilar materials on various substrates with good adhesion.

Claims

1. A polymerizable compound represented by the following general formula (1). (In the general formula (1) above, R represents a hydrogen atom or a methyl group.)

2. The polymerizable compound according to claim 1, wherein the purity measured by HPLC is 80% or higher.

3. The polymerizable compound according to claim 1, used as a composition for forming adhesive or tacky layers or as a material for preparing adhesive or tacky polymers.

4. A method for producing a polymerizable compound according to any one of claims 1 to 3, A method for producing a polymerizable compound, comprising the step of reacting cytidine with 2-isocyanatoethyl (meth)acrylate.

5. A composition for forming adhesive and tack layers containing a polymerizable compound represented by the following general formula (1). (In the general formula (1) above, R represents a hydrogen atom or a methyl group.)

6. The adhesive / tack-forming composition according to claim 5, further comprising a polymerization initiator.

7. The adhesive and bonding layer forming composition according to claim 5 or 6, wherein the content of the polymerizable compound is 0.1 to 10% by mass, based on the solid content.

8. An adhesive polymer having a constituent unit (i) derived from a first polymerizable compound represented by the following general formula (1). (In the general formula (1) above, R represents a hydrogen atom or a methyl group.)

9. The adhesive polymer according to claim 8, wherein the content of the constituent unit (i) is 0.1 to 10% by mass.

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