Raw material composition, method for producing raw material composition, composition for forming adhesive / tacky layer, and adhesive / tacky polymer composition

Abstract

To provide a composition for a raw material capable of preparing a composition for forming an adhesive / pressure-sensitive adhesive layer capable of imparting adhesiveness and pressure-sensitive adhesiveness or further enhancing adhesiveness and pressure-sensitive adhesiveness and forming an adhesive layer or the like excellent in adhesiveness and pressure-sensitive adhesiveness on various substrates.SOLUTION: The raw material composition is used for producing a composition for forming an adhesive and pressure-sensitive adhesive layer. The tannic acid derivative is a reaction product obtained by reacting tannic acid with a compound represented by general formula (3) and contains a compound represented by general formula (1) and the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a raw material composition used for producing a composition for forming an adhesive or pressure-sensitive adhesive layer, a method for producing the same, a composition for forming an adhesive or pressure-sensitive adhesive layer, and an adhesive or pressure-sensitive adhesive polymer composition. [Background technology]

[0002] In recent years, polymers exhibiting various functions have been proposed, which use compounds with a catechol skeleton, such as dopa and dopamine, which are found in marine organisms such as mussels, or their derivatives as monomers. For example, a curable resin composition containing a monomer such as dopamine acrylamide has been proposed (Patent Document 1).

[0003] In addition to catechol skeletons, it has been proposed to use acrylic monomers obtained by converting derivatives of compounds having a pyrogallol skeleton in adhesive compositions and adhesive tapes (Patent Documents 2 and 3). Also, a (meth)acryloyl-based adhesive using a tannic acid derivative having a pyrogallol skeleton in the molecule has been proposed (Patent Document 4). Furthermore, a vinyl alcohol-based adhesive containing unmodified tannic acid has been proposed (Patent Document 5). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2019 / 221135 [Patent Document 2] Patent No. 7150205 [Patent Document 3] Japanese Patent Application Publication No. 2023-127562 [Patent Document 4] Patent No. 3479331 [Patent Document 5] Patent No. 7032517 Summary of the Invention [Problem to be solved by the invention]

[0005] However, compounds such as dopa and dopamine, which are raw materials for the monomer having a catechol skeleton proposed in Patent Document 1, are relatively expensive and difficult to obtain. Furthermore, even when these compounds are used, the properties (adhesion and tackiness) of the adhesive or pressure-sensitive adhesive layer formed are not necessarily sufficient, and there is room for further improvement.

[0006] Furthermore, complicated purification procedures such as neutralization, filtration, separation, and solvent distillation were required to produce the monomers having a pyrogallol skeleton proposed in Patent Documents 2 and 3, and the monomers for preparing the (meth)acryloyl-based adhesives proposed in Patent Document 4. For this reason, there was room for further improvement in mass production of compositions for forming adhesive / tacky layers.

[0007] Furthermore, the adhesive proposed in Patent Document 5 contains water-soluble tannic acid, so it is necessary to use water and a highly polar monomer in combination, which leaves room for further improvement in terms of application to solvent-free types and non-polar monomers.

[0008] The present invention has been made in view of the problems associated with the prior art, and an object of the present invention is to provide a raw material composition that can be used to prepare an adhesive / sticky layer-forming composition that can impart adhesiveness or tackiness or further enhance adhesiveness or tackiness, and form adhesive layers, etc., having excellent adhesiveness and tackiness on various substrates, and a method for producing the same.

[0009] Another object of the present invention is to provide a composition for forming an adhesive / sticky layer, and an adhesive / sticky polymer composition, which can impart adhesiveness or pressure-sensitive adhesiveness or further enhance adhesiveness or pressure-sensitive adhesiveness, and can form adhesive layers and the like having excellent adhesiveness and pressure-sensitive adhesiveness on various substrates. [Means for solving the problem]

[0010] That is, according to the present invention, the raw material composition shown below is provided. [1] A raw material composition used to produce a composition for forming an adhesive / sticky layer, which is a reaction product obtained by reacting tannic acid with a compound represented by the following general formula (3), and which contains a compound represented by the following general formula (1) and a compound represented by the following formula (2).

[0011] TIFF2026009593000001.tif22170 (in the general formula (3), R represents an alkylene group having 2 to 4 carbon atoms)

[0012] TIFF2026009593000002.tif33170 (in the general formula (1), R represents an alkylene group having 2 to 4 carbon atoms)

[0013] TIFF2026009593000003.tif90170

[0014] [2] The raw material composition according to [1], wherein in the general formulae (1) and (3), R is an ethylene group.

[0015] The present invention also provides the following method for producing a raw material composition. [3] A method for producing a raw material composition used to produce a composition for forming an adhesive / sticky layer, the method comprising the step of reacting tannic acid with a compound represented by the following general formula (3):

[0016] TIFF2026009593000004.tif22170 (in the general formula (3), R represents an alkylene group having 2 to 4 carbon atoms)

[0017] [4] The method for producing a raw material composition according to [3], wherein R in the general formula (3) is an ethylene group. [5] A method for producing a raw material composition according to [3] or [4], comprising reacting the tannic acid with the compound represented by general formula (3) in the presence of a Bronsted acid catalyst. [6] The method for producing a raw material composition according to [5] above, wherein the Bronsted acid is p-toluenesulfonic acid.

[0018] Furthermore, according to the present invention, there is provided the following composition for forming an adhesive / tacky layer. [7] A composition for forming an adhesive / sticky layer, comprising the raw material composition according to [1] or [2] above, wherein the content of the compound represented by the general formula (1) is 0.01 to 0.23 mass %, and the content of the compound represented by the formula (2) is 0.009 to 0.018 mass %. [8] The composition for forming an adhesive / sticky layer according to [7] above, further comprising a urethane oligomer having a (meth)acrylic group.

[0019] Furthermore, according to the present invention, there is provided the following polymer composition for forming an adhesive / sticky layer. [9] An adhesive polymer composition comprising a polymer containing a structural unit (i) derived from a compound represented by the following general formula (1) and a compound represented by the following formula (2):

[0020] TIFF2026009593000005.tif33170 (in the general formula (1), R represents an alkylene group having 2 to 4 carbon atoms)

[0021] TIFF2026009593000006.tif90170

[0022]

[10] The adhesive and pressure-sensitive adhesive polymer composition according to [9], wherein in the general formula (1), R is an ethylene group.

[11] The adhesive polymer composition according to [9] or

[10] , wherein the content of the structural unit (i) is 0.01 to 0.23 mass % and the content of the compound represented by formula (2) is 0.009 to 0.018 mass %. [Effects of the Invention]

[0023] According to the present invention, it is possible to provide a raw material composition that can be used to prepare an adhesive / sticky layer-forming composition that can impart adhesiveness or tackiness or further enhance adhesiveness or tackiness and form adhesive layers, etc., that have excellent adhesiveness and tackiness on various substrates, and a method for producing the same.

[0024] Furthermore, according to the present invention, it is possible to provide a composition for forming an adhesive / sticky layer and an adhesive / sticky polymer composition that can impart adhesiveness or pressure-sensitive adhesiveness or further enhance adhesiveness or pressure-sensitive adhesiveness, and can form adhesive layers and the like having excellent adhesiveness and pressure-sensitive adhesiveness on various substrates. DETAILED DESCRIPTION OF THE INVENTION

[0025] <Raw material composition> Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to the following embodiments. One embodiment of the raw material composition of the present invention is a composition used for producing a composition for forming an adhesive / tacky layer, and is a reaction product obtained by reacting tannic acid with a compound represented by the following general formula (3). The raw material composition of this embodiment contains a compound represented by the following general formula (1) and a compound represented by the following formula (2). Hereinafter, the raw material composition of this embodiment will be described in detail.

[0026] TIFF2026009593000007.tif22170 (in the general formula (3), R represents an alkylene group having 2 to 4 carbon atoms)

[0027] TIFF2026009593000008.tif33170 (in the general formula (1), R represents an alkylene group having 2 to 4 carbon atoms)

[0028] TIFF2026009593000009.tif90170

[0029] In general formulas (1) and (3), R is an alkylene group having 2 to 4 carbon atoms, and is most preferably an alkylene group having 2 carbon atoms. That is, R in general formulas (1) and (3) is most preferably an ethylene group. By making R in general formulas (1) and (3) an ethylene group, it is possible to obtain a raw material composition that can be used to produce a composition for forming an adhesive / sticky layer that can form an adhesive layer or the like having excellent adhesiveness and tackiness on various substrates.

[0030] The compound represented by formula (2) is 1,2,3,4,6-penta-O-galloyl-β-D-glucose. The content of the compound represented by general formula (1) in the raw material composition is usually 0.1 to 54 mass%, preferably 0.3 to 36 mass%, and more preferably 1 to 24 mass%, based on the solid content of the raw material composition. The content of the compound represented by formula (2) in the raw material composition is usually 0.09 to 19 mass%, preferably 0.3 to 6 mass%, and more preferably 0.9 to 1.9 mass%, based on the solid content of the raw material composition. By using such a composition, a raw material composition can be easily produced that achieves both a production amount relative to the reaction vessel and an easy-to-handle viscosity.

[0031] In the raw material composition, the content of the compound represented by general formula (1) and the compound represented by formula (2) is preferably (1):(2)=10:90 to 99:1 in mass ratio, more preferably (1):(2)=20:80 to 98:2, particularly preferably (1):(2)=30:80 to 97:3, and most preferably (1):(2)=40:60 to 96:4. By setting the mass ratio of the compound represented by general formula (1) and the compound represented by formula (2) within the above range, a raw material composition can be obtained that can produce an adhesive / pressure-sensitive adhesive layer-forming composition that can form an adhesive layer with excellent adhesion and tackiness between different materials.

[0032] <Method of manufacturing raw material composition> The raw material composition can be produced according to the method shown below. That is, one embodiment of the method for producing a raw material composition of the present invention is a method for producing the raw material composition described above, which includes a step (step (1)) of reacting tannic acid with a compound represented by the following general formula (3):

[0033] TIFF2026009593000010.tif22170 (in the general formula (3), R represents an alkylene group having 2 to 4 carbon atoms)

[0034] In general formula (3), R is an alkylene group having 2 to 4 carbon atoms, preferably an alkylene group having 2 carbon atoms (i.e., an ethylene group). In step (1), tannic acid is reacted with the compound represented by general formula (3). This produces a polymerizable compound represented by general formula (1) and a compound represented by formula (2) (1,2,3,4,6-penta-O-galloyl-β-D-glucose), thereby obtaining the desired raw material composition.

[0035] As described above, the raw material composition is a reaction product obtained by reacting tannic acid with a compound represented by general formula (3). Tannic acid is a compound derived from natural products and is often a mixture that inevitably contains compounds other than tannic acid. Furthermore, the reaction between tannic acid and a compound represented by general formula (3) is thought to produce multiple compounds (reaction products) other than the compound represented by general formula (1) and the compound represented by formula (2), while also producing a complex mixture in which the tannic acid used as a raw material remains. For this reason, it is difficult or substantially impossible to identify the composition of the raw material composition of this embodiment by analytical or other techniques.

[0036] Tannic acid and a compound represented by the following general formula (3) may be reacted at room temperature (25°C) or under heated conditions. When reacting under heated conditions, the reaction temperature is preferably 40 to 100°C, and more preferably 45 to 95°C. By appropriately setting the reaction temperature, it is possible to control the amounts of the compound represented by general formula (1) and the compound represented by formula (2) in the obtained raw material composition.

[0037] A catalyst may be used during the reaction. Examples of the catalyst that can be used include Lewis acids such as dibutyltin laurate, tetra-n-butyl titanate, tetrakis(acetylacetonato)zirconium, zinc 2-ethylhexanoate, and bismuth 2-ethylhexanoate; Bronsted acids such as hydrogen halides, phosphoric acid, sulfuric acid, nitric acid, sulfonic acid, and carboxylic acid; and compounds capable of generating Bronsted acids such as acetyl chloride, acetyl bromide, acetyl iodide, dimethylcarbamoyl chloride, acrylic acid chloride, and methacrylic acid chloride. Among these, it is preferable to use a Bronsted acid as the catalyst, and it is even more preferable to use p-toluenesulfonic acid as the catalyst.

[0038] <Composition for forming adhesive / adhesive layer> By using the raw material composition described above, it is possible to prepare a composition for forming an adhesive or pressure-sensitive adhesive layer that can form an adhesive layer or pressure-sensitive adhesive layer on various substrates. That is, one embodiment of the composition for forming an adhesive or pressure-sensitive adhesive layer of the present invention is a composition containing the raw material composition described above. Hereinafter, the composition for forming an adhesive or pressure-sensitive adhesive layer of this embodiment will be described in detail.

[0039] The content of the compound represented by general formula (1) in the composition for forming an adhesive or pressure-sensitive adhesive layer is preferably 0.001 to 2.4 mass%, more preferably 0.003 to 0.8 mass%, and particularly preferably 0.01 to 0.23 mass%, based on the solid content of the composition for forming an adhesive or pressure-sensitive adhesive layer. Furthermore, the content of the compound represented by formula (2) in the composition for forming an adhesive or pressure-sensitive adhesive layer is preferably 0.0009 to 0.19 mass%, more preferably 0.003 to 0.06 mass%, and particularly preferably 0.009 to 0.018 mass%, based on the solid content of the composition for forming an adhesive or pressure-sensitive adhesive layer. By using such a composition, an adhesive layer or the like having excellent adhesiveness and tackiness can be formed.

[0040] In the composition for forming an adhesive / sticky layer, the content of the compound represented by general formula (1) and the compound represented by formula (2) is preferably a mass ratio of (1):(2) = 10:90 to 99:1, more preferably 20:80 to 98:2, particularly preferably 30:80 to 97:3, and most preferably 40:60 to 96:4. By setting the mass ratio of the compound represented by general formula (1) and the compound represented by formula (2) within the above range, an adhesive or sticking layer with even better adhesion, stickiness, and processability can be formed.

[0041] The composition for forming an adhesive layer may further contain other polymerizable compounds other than the compound represented by general formula (1). As the other polymerizable compounds, conventionally known radically polymerizable compounds constituting ordinary adhesive polymers can be used.

[0042] Examples of radically polymerizable compounds (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, and octadecyl (meth)acrylate. Examples of the alkyl (meth)acrylate include aliphatic, alicyclic, and aromatic alkyl (meth)acrylates such as decyl (meth)acrylate, behenyl (meth)acrylate, isostearyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexylmethyl (meth)acrylate, isobornyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, cyclodecyl (meth)acrylate, cyclodecylmethyl (meth)acrylate, benzyl (meth)acrylate, t-butylbenzotriazole phenylethyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and allyl (meth)acrylate.

[0043] In addition, examples of radically polymerizable compounds (monomers) include (meth)acrylic acid monomers containing a hydroxyl group 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 containing a glycol group; (polyalkylene) glycol monoalkyl, alkylene, alkyne ether, and ester mono(meth)acrylates; (meth)acrylic acid monomers containing an acid group (carboxyl group, sulfonic acid, phosphoric acid) including acrylic acid and acrylic acid dimer; (meth)acrylic acid monomers containing an oxygen atom; (meth)acrylic acid monomers containing an amino group; and (meth)acrylic acid monomers containing a nitrogen atom. Monomers; 2-(meth)acryloyloxyethyl gallate, 3-(meth)acryloyloxypropyl gallate, 4-(meth)acryloyloxybutyl gallate, 5-(meth)acryloyloxypentyl gallate, 6-(meth)acryloyloxyhexyl gallate, 2-(2-(meth)acryloyloxyethylaminocarbonyloxy)ethyl gallate, 3-(2-(meth)acryloyloxyethylaminocarbonyloxy)propyl gallate, 4-(2-(meth)acryloyloxyethylaminocarbonyloxy)propyl gallate mono(meth)acrylates having three or more hydroxyl groups, such as (5-(2-(meth)acryloyloxyethylaminocarbonyloxy)butyl) gallate, (5-(2-(meth)acryloyloxyethylaminocarbonyloxy)pentyl) gallate, and (6-(2-(meth)acryloyloxyethylaminocarbonyloxy)hexyl) gallate; (meth)acrylates containing halogen atoms; (meth)acrylic acid monomers containing silicon atoms; (meth)acrylic acid monomers having an ultraviolet absorbing group; acrylates substituted with methyl hydroxyl groups at the α-position;Examples of such (meth)acrylates include 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.

[0044] Furthermore, as the radically polymerizable compound (monomer), (meth)acrylic acid-based 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, as well as urethane acrylates and oligomers (urethane oligomers having (meth)acrylic groups) can also be used.

[0045] By appropriately blending these radically polymerizable compounds, it is possible to obtain a composition for forming an adhesive / sticky layer with properties suitable for the intended use. The content of the radically polymerizable compound may be appropriately set depending on the purpose and is not particularly limited. The content of the radically polymerizable compound is preferably 5 to 90 mass %, more preferably 10 to 80 mass %, particularly preferably 15 to 70 mass %, and most preferably 20 to 60 mass %, based on the solid content of the composition for forming an adhesive / sticky layer.

[0046] The composition for forming an adhesive / tacky layer may further contain a general compound having polymerizability, such as a vinyl compound such as styrene or vinyl acetate.

[0047] The adhesive / tacky layer-forming composition may further contain a polymerization initiator. Examples of the polymerization initiator include photopolymerization initiators and thermal polymerization initiators. Examples of the photopolymerization initiator 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 benzil dimethyl ketal; benzoins such as benzoin and benzoin methyl ether; benzophenones such as benzophenone, benzoylbenzoic acid, and hydroxybenzophenone; other halogenated ketones, and acylphosphanates.

[0048] Examples of the thermal polymerization initiator that can be used include azo compounds and organic peroxides. Examples of the azo compounds include azobisisobutyronitrile, 1,1'-azobis(cyclohexanecarbonitrile), and 2,2'-azobis(2-methylpropanoate)dimethyl. Examples of the organic peroxides include hydroperoxide compounds, dialkyl peroxide compounds, peroxyester compounds, diacyl peroxide compounds, ketone peroxide compounds, peroxyketal compounds, and peroxydicarbonate compounds.

[0049] The adhesive / tacky layer-forming composition can be made into a coating material with suitable coating properties by further containing a solvent. The solvent can be water or various organic solvents.

[0050] The adhesive layer-forming composition may contain other additives, such as silane coupling agents, thixotropic agents, antiblocking agents, leveling agents, antifoaming agents, antioxidants, thermoplastic resins, antistatic agents, waxes, heat stabilizers, crystallization accelerators, crystallization inhibitors, flame retardants, UV absorbers, antibacterial agents, antiviral agents, and deodorizers.

[0051] The adhesive / adhesive layer-forming composition can be produced by mixing the raw material composition described above with other polymerizable compounds, solvents, polymerization initiators, and other additives. The content of the raw material composition in the resulting adhesive / adhesive layer-forming composition can be appropriately set depending on the purpose. For example, the content of the raw material composition in the adhesive / adhesive layer-forming composition is preferably 0.1 to 80 mass%, more preferably 0.2 to 60 mass%, even more preferably 0.3 to 40 mass%, particularly preferably 0.4 to 20 mass%, and most preferably 0.5 to 10 mass%, based on the solids content of the adhesive / adhesive layer-forming composition.

[0052] An adhesive or pressure-sensitive adhesive layer can be formed by applying a composition for forming an adhesive or pressure-sensitive adhesive layer onto a substrate and curing the resulting coating layer. Methods for applying the composition for forming an adhesive or pressure-sensitive adhesive layer onto a substrate include roll coating, gravure coating, comma coating, knife coating, and die coating.

[0053] When a photopolymerization initiator is used, the coating layer (adhesive / sticky layer-forming composition) can be cured by irradiating the coating layer with a predetermined amount of active energy rays using an irradiation device for active energy rays such as visible light, ultraviolet light, or electron beams. Examples of irradiation devices include a xenon lamp, a xenon-mercury lamp, a metal halide lamp, a high-pressure mercury lamp, a low-pressure mercury lamp, and a fusion lamp. When a thermal polymerization initiator is used, the coating layer can be cured by heating, preferably to 50 to 250°C, using a high-temperature furnace, for example.

[0054] <Adhesive / adhesive polymer composition> One embodiment of the adhesive and pressure-sensitive adhesive polymer composition of the present invention is a composition containing a polymer containing a structural unit (i) derived from a compound represented by the following general formula (1) and a compound represented by the following formula (2). The adhesive and pressure-sensitive adhesive polymer composition of this embodiment contains a polymer containing a structural unit (i) derived from a compound represented by the following general formula (1) and a compound represented by the following formula (2), and therefore can form an adhesive or pressure-sensitive adhesive layer with excellent adhesiveness and tackiness on a variety of substrates. Furthermore, by using the adhesive and pressure-sensitive adhesive polymer composition of this embodiment, an adhesive or pressure-sensitive adhesive layer with excellent adhesion can be formed on a variety of substrates.

[0055] TIFF2026009593000011.tif33170 (in the general formula (1), R represents an alkylene group having 2 to 4 carbon atoms)

[0056] TIFF2026009593000012.tif90170

[0057] In general formula (1), R is an alkylene group having 2 to 4 carbon atoms, and preferably an alkylene group having 2 carbon atoms (that is, an ethylene group).

[0058] The content of the structural unit (i) and the content of the compound represented by formula (2) in the adhesive polymer composition may be appropriately set depending on the purpose. Specifically, the content of the structural unit (i) is preferably 0.001 to 2.4 mass%, more preferably 0.003 to 0.8 mass%, and particularly preferably 0.01 to 0.23 mass%, based on the total amount of the adhesive polymer composition. Furthermore, the content of the compound represented by formula (2) is preferably 0.0009 to 0.19 mass%, more preferably 0.003 to 0.06 mass%, and particularly preferably 0.009 to 0.018 mass%, based on the total amount of the adhesive polymer composition.

[0059] In the adhesive polymer composition, the content of the structural unit (i) and the content of the compound represented by formula (2) is preferably in a mass ratio of (i):(2)=20:80 to 80:20, and more preferably 25:75 to 75:25. By keeping the mass ratio of the structural unit (i) to the compound represented by formula (2) within the above range, an adhesive layer or the like having even better adhesiveness and adhesiveness to both heterogeneous and homogeneous materials can be formed.

[0060] The polymer in the adhesive polymer composition may further contain structural units (other structural units) other than the structural unit (i). The other structural units can be formed using conventionally known polymerizable monomers or resins that constitute ordinary polymers having adhesive or pressure-sensitive adhesive properties.

[0061] <Various products> By using the adhesive / sticky layer-forming composition or adhesive / sticky polymer composition of this embodiment, products such as adhesive sheets can be formed. The adhesive sheet comprises a sheet-like support and a pressure-sensitive adhesive layer formed on one or both sides of the support, the pressure-sensitive adhesive layer being formed from the adhesive / sticky layer-forming composition or the adhesive / sticky polymer composition. Examples of the support include resin films, laminate films containing resin films, paper, woven fabrics, and nonwoven fabrics. Examples of materials for the resin film 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 pressure-sensitive adhesive layer to protect the pressure-sensitive adhesive layer.

[0062] Furthermore, by using the adhesive / sticky layer-forming composition or adhesive / sticky polymer composition, various laminates useful as optical films, etc. can be formed. The laminate is formed by laminating a first substrate and a second substrate via an adhesive layer or a sticking layer formed from the above-mentioned adhesive / sticky layer-forming composition or adhesive / sticky polymer composition. The first substrate and the second substrate may be made of the same material or different materials.

[0063] Materials 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); metal materials such as aluminum (Al), copper (Cu), iron (Fe), gold (Au), platinum (Pt), silver (Ag), zinc (Zn), tin (Sn), titanium (Ti), and alloys thereof; polypropylene (PP), polyethylene (PE), polytetrafluoroethylene (PTFE), polyimide (PI), and polycarbonate (PC). Examples of such materials include organic materials such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polymethyl methacrylate (PMMA), polyphenylene sulfide (PPS), polyphenylene ether (modified PPE), triacetyl cellulose (TAC), cycloolefin polymer (COP), acrylonitrile-butadiene-styrene copolymer (ABS), fiber reinforced plastic (FRP), and molybdenum-aluminum-molybdenum laminate structure (MAM). [Example]

[0064] The present invention will be specifically described below based on examples, but the present invention is not limited to these examples. In the examples and comparative examples, "parts" and "%" are by mass unless otherwise specified.

[0065] Tannic acid used was purchased from Junsei Chemical Co., Ltd. p-Toluenesulfonic acid hydrate, 2-hydroxyethyl methacrylate, and 4-hydroxybutyl acrylate were purchased from Tokyo Chemical Industry Co., Ltd.

[0066] <Production of raw material composition> Example 1 14 parts of tannic acid and 0.7 parts of p-toluenesulfonic acid hydrate were added to 42 parts of 2-hydroxyethyl methacrylate. The mixture was stirred at 50°C for 6 hours to allow the reaction to proceed, yielding 60 parts of raw material composition 1 containing a compound represented by the following formula (A) and a compound represented by formula (2). Measurement by LC-MS (high performance liquid chromatography mass spectrometry) revealed that the content of the compound represented by formula (A) in raw material composition 1 was 1.0%, and the content of the compound represented by formula (2) was 1.5%.

[0067] TIFF2026009593000013.tif34170

[0068] The contents of the compound represented by general formula (1) and the compound represented by formula (2) were calculated by comparing the peak area of ​​an MRM chromatogram, which records the intensity of ions derived from the compounds, obtained by LC-MS (high performance liquid chromatography mass spectrometry) measurement with the peak area obtained when measuring standard substances of various concentrations. The standard substance of the compound represented by general formula (1) was a compound synthesized by the method described in Patent Document 2. The standard substance of the compound represented by formula (2) was a reagent purchased from Cayman Chemical Company. The LC-MS measurement conditions are shown below.

[0069] [LC-MS measurement conditions] Analytical equipment: LC-30AD, SPD-M20A, and LCMS-8050 LCMS system (Shimadzu Corporation) Eluent: acetonitrile-0.1% acetic acid aqueous solution (1:19 → 17:3 (v / v), gradient over 40 minutes) Flow rate: 0.2mL / min Column: L-column 2 ODS. 2 μm (3.0 × 100 mm) (Chemicals Evaluation and Research Institute, Inc.) Column temperature: 40℃ Sample: 10 μL of 100 ppm THF solution

[0070] (Examples 2 to 4, Comparative Example 1) Raw material compositions 1 to 5 were obtained in the same manner as in Example 1, except that the types and amounts of components shown in Table 1 were used and the reaction temperatures and times were set as shown in Table 1. Table 1 shows the contents of the compound represented by formula (A) and the compound represented by formula (2) in the obtained raw material compositions.

[0071] (Comparative Example 2) The compound represented by formula (A) synthesized according to the description of Patent Document 2 was designated as raw material composition 6. The content (purity) of the compound represented by formula (A) in raw material composition 6 was 92.0%.

[0072] (Comparative Example 3) A commercially available compound represented by the following formula (B) was used as raw material composition 7.

[0073] TIFF2026009593000014.tif21170

[0074] TIFF2026009593000015.tif88170

[0075] <Production of composition for forming adhesive / sticky layer> Example 5 A composition for forming an adhesive / sticky layer (paint) was obtained by mixing 50 parts of UV-curable urethane acrylate (UV-3700B) (product name "Shikou UV-3700B", manufactured by Mitsubishi Chemical Corporation, a urethane oligomer having a (meth)acrylic group), 5 parts of a polymerization initiator (diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO)), 49 parts of an acrylic monomer (tetrahydrofurfuryl acrylate (THFA)), and 1 part of raw material composition 1.

[0076] (Examples 6 to 8, Comparative Examples 4 to 6, Reference Example 1) A composition for forming an adhesive / tacky layer (paint) was obtained in the same manner as in Example 5 above, except that the formulation (unit: parts) shown in Table 2 was used.

[0077] TIFF2026009593000016.tif97170

[0078] <Evaluation of compositions for forming adhesive / sticky layers> (OCR evaluation (evaluation of adhesive strength)) The produced paint was applied to a glass plate to form a coating layer. The adhesive surface of a polyethylene terephthalate (PET) film was placed on the formed coating layer and laminated, and then the coating layer was cured by UV irradiation. After leaving it for 3 days, it was cut into strip-shaped test pieces and the peel strength was measured. The peel strength of the test piece obtained using the paint of 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 also shown in Table 3. ◎: 200% or more ○: 100% or more but less than 200% △: 50% or more but less than 100% ×: Less than 50%

[0079] TIFF2026009593000017.tif74170 [Industrial Applicability]

[0080] The composition for forming an adhesive / tacky layer of the present invention is useful as a material for forming an adhesive layer or the like having excellent adhesiveness and tackiness to different materials on various substrates.

Claims

1. A raw material composition used to produce a composition for forming an adhesive / tacky layer, It is a reaction product obtained by reacting tannic acid with a compound represented by the following general formula (3): A raw material composition containing a compound represented by the following general formula (1) and a compound represented by the following formula (2): (In the general formula (3), R represents an alkylene group having 2 to 4 carbon atoms.) (In the general formula (1), R represents an alkylene group having 2 to 4 carbon atoms.)

2. 2. The raw material composition according to claim 1, wherein in the general formulas (1) and (3), R is an ethylene group.

3. A method for producing a raw material composition used to produce a composition for forming an adhesive / tacky layer, comprising: A method for producing a raw material composition, comprising a step of reacting tannic acid with a compound represented by the following general formula (3): (In the general formula (3), R represents an alkylene group having 2 to 4 carbon atoms.)

4. 4. The method for producing a raw material composition according to claim 3, wherein in the general formula (3), R is an ethylene group.

5. 5. The method for producing a raw material composition according to claim 3 or 4, wherein the tannic acid and the compound represented by general formula (3) are reacted in the presence of a Bronsted acid as a catalyst.

6. 6. The method for producing a raw material composition according to claim 5, wherein the Bronsted acid is p-toluenesulfonic acid.

7. A raw material composition according to claim 1 or 2, The content of the compound represented by the general formula (1) is 0.01 to 0.23 mass %, A composition for forming an adhesive / sticky layer, wherein the content of the compound represented by formula (2) is 0.009 to 0.018% by mass.

8. The composition for forming an adhesive / sticky layer according to claim 7 , further comprising a urethane oligomer having a (meth)acrylic group.

9. a polymer containing a structural unit (i) derived from a compound represented by the following general formula (1); An adhesive polymer composition comprising a compound represented by the following formula (2): (In the general formula (1), R represents an alkylene group having 2 to 4 carbon atoms.)

10. 10. The adhesive and pressure-sensitive adhesive polymer composition according to claim 9, wherein in the general formula (1), R is an ethylene group.

11. the content of the structural unit (i) is 0.01 to 0.23% by mass, The adhesive and pressure-sensitive adhesive polymer composition according to claim 9 or 10, wherein the content of the compound represented by formula (2) is 0.009 to 0.018% by mass.

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