JP5994424B2 - UV-curable adhesive resin composition and adhesive - Google Patents

Description

  The present invention relates to a resin composition for an ultraviolet curable pressure-sensitive adhesive and a pressure-sensitive adhesive laminate that are excellent in adhesive strength and step following ability.

  Since the ultraviolet curable pressure-sensitive adhesive usually does not contain a solvent such as a solvent or water, it does not require a step of removing a solvent such as a solvent or water when forming the pressure-sensitive adhesive layer. Is widely used in the manufacture of optical related products.

  Among the optical related products, cellular phones, liquid crystal televisions, personal computers, etc. are a collection of various members such as polarizing plates, brightness enhancement films, retardation films, color filters, etc. The agent is being used.

  Examples of the ultraviolet curable pressure-sensitive adhesive used for the mobile phone, the liquid crystal television, and the personal computer include (meth) acrylic polymers (component A), carboxylic acids having a polymerizable unsaturated group, and oligomers thereof. Constituents comprising at least one (B component), a photopolymerization initiator (C component), a silane coupling agent (D component), and a compound having a polymerizable unsaturated group other than the A component and the B component (E component) The component A contains a repeating unit derived from a (meth) acrylic monomer in the main chain, and has a (meth) acryloyl functional group containing a (meth) acryloyl skeleton in the side chain, It contains 0.5 to 20 mmol of the (meth) acryloyl functional group per 100 g of coal, glass transition temperature (Tg) is −55 to 0 ° C., and weight average molecular weight (Mw) is in the range of 200,000 to 1,000,000. It is a crosslinkable (meth) acrylic polymer, the C component is an acyl phosphine oxide photopolymerization initiator, the D component is a silane coupling agent having an epoxy functional group, and the A component And when the total amount of the B component is 100 parts by mass, the A component is 80 to 99.5 parts by mass, the B component is 0.5 to 20 parts by mass, and the C component is 0.05 to 3 parts by mass. A pressure-sensitive adhesive using an ultraviolet curable pressure-sensitive adhesive composition containing 0.1 to 5 parts by mass of the D component and 0 to 20 parts by mass of the E component is known (see, for example, Patent Document 1). ).

  However, the current mainstream optical members (adherents) have various steps such as various printed patterns and wirings, and when the adhesive is used, the adhesive is completely filled in the steps. However, since bubbles and voids are generated around the step (poor step following ability is poor), there is a problem that adversely affects the optical performance.

JP 2010-265440 A

  The problem to be solved by the present invention is for an ultraviolet curable pressure-sensitive adhesive that has excellent adhesive strength at a level that does not cause peeling over time with respect to a substrate made of various materials, and has excellent step following ability. It is to provide a resin composition.

  The inventors of the present invention have made extensive research to solve the above-mentioned problems, and paid attention to the combination of a urethane (meth) acrylate resin and a (meth) acrylic monomer and advanced the research.

  As a result, it has been found that when a urethane (meth) acrylate having a specific acryloyl group equivalent is used, an adhesive having excellent adhesive force and step following ability can be obtained.

  That is, the present invention provides a urethane (meth) acrylate resin (A) obtained by reacting a polyol (a), a polyisocyanate (b) and a (meth) acrylic compound (c) having a hydroxyl group, and a (meth) acrylic monomer. The resin composition for ultraviolet curable adhesives containing a body (B) and a photoinitiator (C), Comprising: The equivalent of the (meth) acryloyl group of the said urethane (meth) acrylate resin (A) is 8 The resin composition for an ultraviolet curable pressure-sensitive adhesive and the pressure-sensitive adhesive are characterized by being in the range of 1,000 to 17,000.

  The pressure-sensitive adhesive obtained by using the resin composition for ultraviolet curable pressure-sensitive adhesive of the present invention has excellent adhesive force, holding force and step following ability.

  The pressure-sensitive adhesive obtained by using the resin composition for an ultraviolet curable pressure-sensitive adhesive of the present invention can be suitably used as a pressure-sensitive adhesive used for an optical member. In particular, it can be suitably used for the production of touch panels, liquid crystal displays, plasma displays, organic EL, personal computers, mobile phones and the like.

  Moreover, in this invention, when a specific thing is used as said (meth) acryl monomer (B), the adhesive which is excellent in the whitening resistance after wet heat is obtained.

  Moreover, the adhesive which is excellent in moisture heat resistance (adhesion power retention after heat-and-moisture resistance) is obtained by further containing a silane coupling agent in the resin composition for ultraviolet curable adhesives of this invention.

  First, the urethane (meth) acrylate resin (A) used in the present invention will be described.

  Examples of the polyol (a) include polyester polyol, polyether polyol, polycarbonate polyol, polyacryl polyol, polybutadiene polyol, and the like. These may be used alone or in combination of two or more. Among these, polyether polyols and polycarbonate polyols are preferably used from the viewpoint of further improving the adhesive strength, holding power, step following ability, whitening resistance, and the like.

  Examples of the polyether polyol include products obtained by addition polymerization of one or more alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, etc., to a compound having two or more active hydrogens, Examples include polytetramethylene glycol obtained by ring-opening polymerization of tetrahydrofuran, modified polytetramethylene glycol obtained by copolymerization of tetrahydrofuran and alkyl-substituted tetrahydrofuran, and modified polytetramethylene glycol obtained by copolymerization of neopentyl glycol and tetrahydrofuran. .

  Examples of the compound having two or more active hydrogens include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, dipropylene glycol, tripropylene glycol, 1 , 2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,5-hexanediol, 1,6-hexanediol, 2, 5-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 2-methyl -1,3-propanediol, neopentyl glycol 2-butyl-2-ethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-ethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2- Relatively low molecular weight dihydroxy compounds such as ethyl-1,3-hexanediol, 2-methyl-1,8-octanediol, hydroquinone, resorcin, bisphenol A, bisphenol F, 4,4′-bisphenol, -Cyclobutanediol, 1,3-cyclopentanediol, 1,4-cyclohexanediol, cycloheptanediol, cyclooctanediol, 1,4-cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo [5,2,1,0, 2,6] decane-dimethanol, bicyclo [4,3,0 Nonanediol, dicyclohexanediol, tricyclo [5,3,1,1] dodecanediol, bicyclo [4,3,0] nonanedimethanol, tricyclo [5,3,1,1] dodecane-diethanol, hydroxypropyltri Cyclo [5,3,1,1] dodecanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1′-bicyclohexylidenediol, cyclohexanetriol, hydrogenated bisphenol A, 1,3-adamantane Examples include alicyclic polyols such as diols, polyether polyols such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol, and polyester polyols such as polyhexamethylene adipate, polyhexamethylene succinate, and polycaprolactone. I can get lost.

  Among these, it is more preferable to use an aliphatic polyether polyol from the viewpoint of imparting good adhesive properties, and it is particularly preferable to use polytetramethylene glycol obtained by ring-opening polymerization of tetrahydrofuran.

  The number average molecular weight of the polyether polyol is preferably in the range of 500 to 3,000, more preferably in the range of 500 to 2,000, and still more preferably in the range of 500 to 1,500. In addition, the number average molecular weight of the said polyether polyol is the value calculated | required by polystyrene conversion using gel permeation chromatography (GPC).

  Examples of the polycarbonate polyol include those obtained by reacting a carbonate and / or phosgene with the compound having two or more active hydrogens.

  Examples of the carbonate ester include methyl carbonate, dimethyl carbonate, ethyl carbonate, diethyl carbonate, cyclocarbonate, diphenyl carbonate, and the like.

  The hydroxyl value of the polycarbonate polyol is preferably 30 to 230 mgKOH / g, more preferably 50 to 230 mgKOH / g, from the viewpoint of adhesive strength and the like. In addition, the hydroxyl value of the said polycarbonate polyol shows the value which measured based on JISK0070.

  Examples of the polyisocyanate (b) include aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4. Examples include aliphatic or alicyclic diisocyanates such as' -dicyclohexylmethane diisocyanate, diisocyanate methylcyclohexane, and tetramethylxylylene diisocyanate. These may be used alone or in combination of two or more. Among these, the use of a diisocyanate having an alicyclic structure is preferable from the viewpoint of achieving both excellent adhesive strength and holding power and improving heat-resistant yellowing, and the like, 4,4′-dicyclohexylmethane diisocyanate, More preferably, isophorone diisocyanate, cyclohexane diisocyanate, or diisocyanate methylcyclohexane is used.

  The (meth) acrylic compound (c) having a hydroxyl group is used to introduce a (meth) acryloyl group into the urethane (meth) acrylate resin (A) and can react with an isocyanate group. It is what has.

  Examples of the (meth) acrylic compound having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl acrylate, 3-hydroxybutyl (meth) acrylate, and 4-hydroxy. (Meth) acrylic acid alkyl ester having a hydroxyl group such as butyl (meth) acrylate, 6-hydroxyhexyl acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, etc. And polyfunctional (meth) acrylate having a hydroxyl group, polyethylene glycol monoacrylate, polypropylene glycol monoacrylate and the like. Among these, from the viewpoint of curability by ultraviolet rays, it is more preferable to use an acrylic compound having a hydroxyl group. From the viewpoint of easy availability of raw materials, curability, and good adhesive properties, 2-hydroxyethyl can be used. Particularly preferred are acrylates and 4-hydroxybutyl acrylate.

  As a method for producing the urethane (meth) acrylate resin (A), for example, after the polyol (a) and the (meth) acrylic compound (c) are charged into a reaction system in the absence of a solvent, A method of producing by supplying isocyanate (b), mixing and reacting, or urethane having an isocyanate group at the molecular terminal by reacting the polyol (a) and the polyisocyanate (b) in the absence of a solvent. Examples thereof include a method in which a prepolymer is obtained, and then the (meth) acrylic compound (c) is supplied, mixed and reacted. In any case, the reaction is preferably carried out under a condition of 20 to 120 ° C. for about 30 minutes to 24 hours.

  The urethane (meth) acrylate resin (A) may be produced in the presence of an organic solvent or an aqueous medium. Furthermore, it may be produced in the presence of a (meth) acrylic monomer (B) described later, instead of an organic solvent or an aqueous medium. In particular, when manufacturing a laminate, it is not necessary to remove the organic solvent or aqueous medium and the manufacturing process can be simplified. From the viewpoint of suppressing viscosity in the absence of solvent or in the reaction system, (meth) acrylic It is preferable to carry out in the presence of the monomer (B).

  The reaction of the polyol (a), the polyisocyanate (b), and the (meth) acrylic compound (c) is the sum of the hydroxyl groups of the polyol (a) and the hydroxyl groups of the (meth) acrylic compound (c). The urethane (meth) acrylate resin (A) obtained by carrying out in an amount ratio [the total amount of isocyanate groups / hydroxyl groups] = 0.75 to 1.00 between the amount and the isocyanate group of the polyisocyanate (b) ) Is preferable in controlling the molecular weight, and more preferably in the range of 0.79 to 0.95. The reaction may be carried out when the equivalent ratio exceeds 1, but in that case, an alcohol such as methanol is used for the purpose of deactivating the terminal isocyanate group of the urethane (meth) acrylate resin (A). Is preferred. In that case, the total amount of the hydroxyl group of the polyol (a), the hydroxyl group of the (meth) acrylic compound (c) and the hydroxyl group of the alcohol, and the equivalent ratio of the polyisocyanate group [isocyanate group / hydroxyl group It is preferable to adjust so that [total amount] is within the above range.

  Moreover, as alcohol which can be used in order to inactivate the terminal isocyanate group of the said urethane (meth) acrylate resin (A), monofunctional alcohols, such as methanol, ethanol, a propanol, a butanol, 1, 2, for example, -Bifunctional alcohols composed of primary and secondary hydroxyl groups such as propylene glycol and 1,3-butylene glycol may be used.

  Moreover, when manufacturing urethane (meth) acrylate resin (A), you may use a polymerization inhibitor, a urethanization catalyst, etc. as needed.

  Examples of the polymerization inhibitor include 3,5-bismutual butyl-4-hydroxytoluene, hydroquinone, methyl hydroquinone, hydroquinone monomethyl ether (methoquinone), para-tertiary butyl catechol methoxyphenol, 2,6-ditertiary butyl cresol. Phenothiazine, tetramethylthiuram disulfide, diphenylamine, dinitrobenzene and the like can be used.

  Examples of the urethanization catalyst include nitrogen-containing compounds such as triethylamine, triethylenediamine and N-methylmorpholine, metal salts such as potassium acetate, zinc stearate and tin octylate, and organometallic compounds such as dibutyltin laurate. Can be used.

  The urethane (meth) acrylate resin (A) has a (meth) acryloyl group that allows radical polymerization to proceed by light irradiation, heating, or the like. In order to solve the problems of the present invention, the equivalent of the (meth) acryloyl group is in the range of 8,000 to 17,000. When the equivalent is less than 8,000, the crosslinking density increases and the step following ability becomes poor. When the equivalent is more than 17,000, the crosslinking density is decreased, so that the desired adhesive force and holding power are obtained. May not be obtained or an adhesive may not be obtained. The equivalent of the (meth) acryloyl group is more preferably in the range of 9,100 to 16,000, more preferably in the range of 9,500 to 15,500, from the viewpoint that the step following ability can be further improved. A range of 000 to 15,000 is particularly preferred. In addition, the equivalent of the (meth) acryloyl group is the total mass of the polyol (a), polyisocyanate (b), and (meth) acrylic compound (c) in the urethane (meth) acrylate resin (A). The value divided by the equivalent of the (meth) acryl group present is shown. In the present invention, “(meth) acrylic compound” refers to one or both of a methacrylic compound and an acrylic compound, and “(meth) acrylate” refers to one or both of methacrylate and acrylate. ") Acryloyl group" means one or both of methacryloyl group and acryloyl group, and "(meth) acrylic acid" means one or both of methacrylic acid and acrylic acid, and "(meth) acrylic monomer" Means one or both of a methacrylic monomer and an acrylic monomer.

  The weight average molecular weight of the urethane (meth) acrylate resin (A) is 5,000 to 50,000 from the viewpoint of achieving both excellent adhesive force and holding power and imparting good coating workability. Is preferable, the range of 7,000 to 45,000 is more preferable, the range of 10,000 to 40,000 is still more preferable, and the range of 12,000 to 3,5000 is particularly preferable. In addition, the weight average molecular weight of the said urethane (meth) acrylate resin (A) is the value calculated | required by polystyrene conversion using the gel permeation chromatography (GPC).

  Next, the (meth) acrylic monomer (B) used in the present invention will be described.

  Examples of the (meth) acrylic monomer (B) include methyl acrylate (glass transition temperature (Tg): 10 ° C.), ethyl acrylate (−24 ° C.), propyl acrylate (−37 ° C.), acrylic Isopropyl (-6 ° C), butyl acrylate (-49 ° C), sec-butyl acrylate (-22 ° C), isobutyl acrylate (-24 ° C), 2-ethylbutyl acrylate (-50 ° C), acrylic acid n-pentyl (-57 ° C), hexyl acrylate (-57 ° C), 2-ethylhexyl acrylate (-50 ° C), heptyl acrylate (-60 ° C), octyl acrylate (-65 ° C), acrylic acid 2 -Octyl (-45 ° C), nonyl acrylate (-58 ° C), dodecyl acrylate (-3 ° C), 3-methoxybutyl acrylate (-56 ° C), 2-acrylic acid 2- Toxiethyl (-50 ° C), 3-methoxypropyl acrylate (-75 ° C), 2-methoxybutyl acrylate (-32 ° C), 3-methylbutyl acrylate (-45 ° C), benzyl acrylate (6 ° C), Pentyl methacrylate (−5 ° C.), hexyl methacrylate (−5 ° C.), 2-ethylhexyl methacrylate (−10 ° C.) (the Tg value is reprinted from Polmer Handbook (4th ed.)), 2-hydroxy acrylate Ethyl (HEA; -15 ° C), 2-hydroxypropyl acrylate (HPA; -7 ° C), 4-hydroxybutyl acrylate (4HBA; -32 ° C), isooctyl acrylate (IOAA; -58 ° C), acrylic acid Lauryl (LA; 15 ° C), stearyl acrylate (STA; -58 ° C), tetrahydrophrate acrylate Rufuryl (Biscoat # 150; -12 ° C), benzyl acrylate (Biscoat # 160; 6 ° C), ethyl carbitol acrylate (Biscoat # 190; -67 ° C), phenoxyethyl acrylate (Biscoat # 192; -22 ° C) (Osaka Organic Chemical Co., Ltd., Tg value reprinted from the company's HP), methoxypolyethylene glycol acrylate (EO 9 mol, AM-90G; -71 ° C.), phenoxypolyethylene glycol acrylate (AMP-20GY; -8) ° C) (Shin Nakamura Chemical Co., Ltd., Tg value reprinted from the company's HP), Isoamyl acrylate (IAA; -45 ° C), Ethoxyacrylate-diethylene glycol (EC-A; -70 ° C) (above , Kyoeisha Chemical Co., Ltd., Tg value reprinted from the company's HP), Neope Acrylate Chill (22 ° C), cyclohexyl acrylate (19 ° C), hexadecyl acrylate (35 ° C), isobornyl acrylate (94 ° C), phenyl acrylate (57 ° C), acrylamide (165 ° C), benzyl methacrylate (54 ° C ), Methyl methacrylate (105 ° C), ethyl methacrylate (65 ° C), propyl methacrylate (35 ° C), isopropyl methacrylate (81 ° C), butyl methacrylate (20 ° C), isobutyl methacrylate (53 ° C), Sec-butyl methacrylate (60 ° C), t-butyl methacrylate (118 ° C), cyclohexyl methacrylate (83 ° C) 2-hydroxyethyl methacrylate (85 ° C), isobornyl methacrylate (110 ° C) (above, Polymer Handbook) (Reproduced Tg value from 4th ed.) T-butyl acrylate (TBA; 41 ° C) (Osaka Organic Chemical Co., Ltd., Tg value reprinted from HP), 2-hydroxy-3-phenoxypropyl acrylate (M-600A; 17 ° C) (Reproduced from Kyoeisha Chemical Co., Ltd., Tg value reprinted from HP), dimethylacrylamide (DMAA; 119 ° C), acryloylmorpholine (ACMO; 145 ° C), dimethylaminopropylacrylamide (DMAPAA; 134 ° C), isopropylacrylamide (NIPAM; 134 ° C.), diethyl acrylamide (DEAA; 81 ° C.), hydroxyethyl acrylamide (HEAA; 98 ° C.) (manufactured by Kojin Co., Ltd., reprinted Tg value from HP). These monomers may be used alone or in combination of two or more. The Tg value represents the Tg of the homopolymer of the (meth) acrylic monomer, and Polymer Handbook (4th ed.) And (meth) acrylic monomer manufacturer homepage values were used. .

  As the (meth) acrylic monomer (B), not only adhesive strength, holding power, and step following ability, but the present invention is an optical related product such as a touch panel, a liquid crystal display, a plasma display, an organic EL, a personal computer, and a mobile phone. (Meth) acrylic monomer (meth) acrylic capable of forming a homopolymer having a glass transition temperature of 15 ° C. or lower from the viewpoint of further improving the whitening resistance after heat and moisture resistance. Use of a mixture of at least one monomer (B-1) and at least one (meth) acrylic monomer (B-2) capable of forming a homopolymer having a glass transition temperature higher than 15 ° C. Is preferred.

  Moreover, as mass ratio [(B-1) / (B-2)] of the said (meth) acrylic monomer (B-1) and the said (meth) acrylic monomer (B-2), it is 90. The range of / 10 to 10/90 is preferable from the viewpoint of further improving the physical properties of pressure-sensitive adhesive, the step following ability and the whitening resistance due to the cohesive force. Moreover, it is more preferable that it is the range of 85 / 15-20 / 80, the range of 82 / 18-40 / 60 is still more preferable, the range of 80 / 20-60 / 40 is still more preferable, 75 / 25-60 / A range of 40 is particularly preferred.

  Among the above-mentioned (meth) acrylic monomers (B-1), among those described above, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, 2-methoxyethyl acrylate, 2-hydroxy acrylate It is preferable to use ethyl and 4-hydroxybutyl acrylate, and particularly preferable to use butyl acrylate and 2-ethylhexyl acrylate because excellent tackiness can be imparted.

  Moreover, as said (meth) acryl monomer (B-2), it is preferable to use what has a nitrogen atom among above mentioned from viewpoints of the adhesive physical property by cohesive force, whitening resistance, etc., and dimethylacrylamide Acryloylmorpholine, dimethylaminopropylacrylamide, isopropylacrylamide, diethylacrylamide, and hydroxyethylacrylamide are more preferable, and dimethylacrylamide is particularly preferable.

  As the amount of the (meth) acrylic monomer (B) used, it is possible to achieve both excellent adhesive strength and holding power, and from the viewpoints of coating property due to viscosity and the like, step followability, etc., the urethane (meth) acrylate It is preferable to use in the range of 30-200 mass parts with respect to 100 mass parts of resin (A), The range of 50-150 mass parts is more preferable, The range of 70-130 mass parts is especially preferable.

  Next, the photopolymerization initiator (C) used in the present invention will be described.

  The photopolymerization initiator (C) generates radicals by light irradiation, heating, or the like, and initiates radical polymerization of the urethane (meth) acrylate resin (A) or the (meth) acrylic monomer (B).

  Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy- 2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 2-methyl- [4- (methylthio) phenyl]- Acetophenones such as 2-morpholino-1-propanone and 2,2-dimethoxy-2-phenylacetophenone; benzoins such as benzoin, benzoin methyl ether, benzoin isoethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzopheno Benzophenones such as benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3′-dimethyl-4-methoxybenzophenone; thioxanthone, 2-chloro Thioxanthones such as thioxanthone, 2,4-dichlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone; 4,4′-dimethylaminothioxanthone (Also known as Minerals ketone), 4,4′-diethylaminobenzophenone, α-acyloxime ester, benzyl, methylbenzoylformate (“Biacure 55”), Anthraquinones such as 2-ethylanthraquinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide (“Lucirin TPO”), bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (“IRGACURE819”), etc. Acylphosphine oxides; 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone [“BTTB” manufactured by NOF Corporation], acrylated benzophenone, and the like.

  As the photopolymerization initiator, 2-hydroxy-2-methyl- can be used from the viewpoints of achieving both excellent adhesive strength and holding power, preventing discoloration of the adhesive layer over time, and improving curability. It is preferable to use 1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide.

  The photopolymerization initiator (C) is preferably used in an amount of 0.1 to 20 parts by mass with respect to 100 parts by mass of the urethane (meth) acrylate resin (A). The range of parts by mass is more preferable, and the range of 1 to 5 parts by mass is particularly preferable.

  In addition, when the pressure-sensitive adhesive obtained using the resin composition for UV-curable pressure-sensitive adhesive of the present invention is used for the production of optical related products, the UV-curable pressure-sensitive adhesive composition of the present invention is further added to a silane cup. It is preferable from the viewpoint that moisture and heat resistance can be imparted by containing the ring agent (D).

  Examples of the silane coupling agent (D) include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyl. Silane coupling agents having an epoxy group such as methyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4 -Epoxycyclohexyl) ethylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) propyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) Propylmethyldimethoxy Silane coupling agents having an alicyclic epoxy group such as lan, 2- (3,4-epoxycyclohexyl) propyltriethoxysilane, 2- (3,4-epoxycyclohexyl) propylmethyldiethoxysilane, vinyltrichlorosilane, vinyl Trimethoxysilane, vinyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltri Ethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, silicone alkoxy oligomer, etc. These may be used in combination of two or more kinds thereof may be used alone.

  Among these, it is preferable to use a silane coupling agent having an epoxy group or a silane coupling agent having an alicyclic epoxy group from the viewpoint of further improving the heat and moisture resistance, and 2- (3,4-epoxycyclohexyl) ethyltri Use of one or more selected from the group consisting of ethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane and 3-glycidoxypropyltriethoxysilane More preferred.

  The amount of the silane coupling agent (D) used is in the range of 0.01 to 10 parts by mass with respect to 100 parts by mass of the urethane (meth) acrylate resin (A). It is preferable from a viewpoint which can provide yellowing, The range of 0.05-5 mass parts is more preferable, The range of 0.05-1 mass part is especially preferable.

  Next, the ultraviolet curable adhesive resin composition of the present invention will be described.

  The resin composition for an ultraviolet curable pressure-sensitive adhesive according to the present invention is, for example, a urethane (meth) acrylate resin (A) produced alone, and then a (meth) acrylic monomer (B), a photopolymerization initiator (C). And, if necessary, the method of mixing the silane coupling agent (D), or the urethane (meth) acrylate resin (A) in the presence of part or all of the (meth) acrylic monomer (B). It can manufacture by the method of manufacturing and mixing a polymerization initiator (C) and a silane coupling agent (D) if necessary.

  The ultraviolet curable pressure-sensitive adhesive resin composition obtained by the above method is not particularly limited, but from the viewpoint of good coating properties and good handling of the pressure-sensitive adhesive solution during coating, 500 to 20,000 mPa · s. The range of 1,000 to 15,000 mPa · s is more preferable, and the range of 5,000 to 10,000 mPa · s is more preferable in order to further improve the step following ability. In addition, the said viscosity shows the value measured with the B-type viscometer at 25 degreeC.

  Moreover, the resin composition for ultraviolet curable adhesives of this invention may contain another additive other than what was mentioned above.

  Examples of the other additives include rust preventives, thixotropic agents, sensitizers, polymerization inhibitors, curing agents, curing accelerators, leveling agents, tackifiers, waxes, heat stabilizers, antistatic agents, Flame retardants, foam stabilizers, antifoaming agents, antiseptics, antiblocking agents, light-resistant stabilizers, antioxidants and the like can be used.

  Moreover, the resin composition for ultraviolet curable adhesives of this invention is the said urethane (meth) acrylate resin (A), the said (meth) acryl monomer (B), the said photoinitiator (C), and a necessity Depending on the above, the other additives and the like may be dissolved or dispersed in a solvent such as an organic solvent or an aqueous medium, but the urethane (meta) is added to the (meth) acrylic monomer (B). ) When the acrylate resin (A), the photopolymerization initiator (C), etc. are dissolved or dispersed, the base material is bonded to produce a laminate to remove the solvent contained in the adhesive. This is preferable because a process is unnecessary and the production efficiency of the laminate can be improved.

  The ultraviolet curable pressure-sensitive adhesive resin composition of the present invention can be cured by irradiation with energy rays such as ultraviolet rays.

  As a method for curing the ultraviolet curable adhesive resin composition of the present invention, for example, a known ultraviolet light irradiation device such as a xenon lamp, a xenon-mercury lamp, a metal halide lamp, a high pressure mercury lamp, a low pressure mercury lamp, or the like is used. It can be cured by irradiating with predetermined ultraviolet rays.

The ultraviolet irradiation is preferably in the range of 0.05 to 5 J / cm ² , more preferably 0.1 to 3 J / cm ² , and particularly preferably 0.3 to 1.5 J / cm ² . In addition, the ultraviolet irradiation amount was based on a value measured in a wavelength range of 300 to 390 nm using a UV checker UVR-N1 (manufactured by GS Yuasa Co., Ltd.).

  Moreover, when the resin composition for ultraviolet curable adhesives of this invention contains the said other additive, as needed, by heating at about 40-80 degreeC after the said ultraviolet irradiation, Curing may be further accelerated.

  As a base material which can apply the resin composition for UV curable pressure sensitive adhesive of the present invention to form a pressure sensitive adhesive layer, a plastic base material, a flexible printed base material, a glass base material, and ITO are deposited on these base materials. And the like.

As said plastic base material, the base material and PC which consist of generally used acrylic resin etc.
(Polycarbonate), PBT (polybutylene terephthalate), PPS (polyphenylene sulfide), modified PPE (polyphenylene ether), PET (polyethylene terephthalate), COP (cycloolefin polymer), TAC (triacetyl cellulose), antireflection film or sheet, Examples thereof include an antifouling film or sheet, and a film or sheet of a transparent conductive film constituting the touch panel.

  EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the scope of the present invention is not limited only to these examples.

  Further, in the present invention, unless otherwise specified, “part” is “part by mass” and “%” is “mass%”.

[Synthesis Example 1]
<Synthesis of urethane acrylate resin (A-1)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 460 parts by mass of polytetramethylene glycol (number average molecular weight; 1,000), 6.5 parts by mass of 2-hydroxyethyl acrylate, 2, 2 parts by mass of 6-di-tert-butyl-cresol and 0.3 parts by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 105 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-1). The obtained urethane acrylate resin (A-1) has an acryloyl group equivalent of 10,208 (rounded off to the nearest decimal point. The molecular weight of 2-hydroxyethyl acrylate was 116.1. The same applies hereinafter) and the weight average molecular weight. 26,000.

[Synthesis Example 2]
<Synthesis of urethane acrylate resin (A-2)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 653 parts by mass of polycarbonate polyol (Kuraray polyol C-3090, manufactured by Kuraray Co., Ltd.), 7.8 parts by mass of 2-hydroxyethyl acrylate, 2,6-di-tertiary butyl-cresol 2 parts by mass and p-methoxyphenol 0.3 part by mass were added. After raising the temperature in the reaction vessel to 40 ° C., 47 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-2). The obtained urethane acrylate resin (A-2) had an acryloyl group equivalent of 10,535 and a weight average molecular weight of 32,000.

[Synthesis Example 3]
<Synthesis of urethane acrylate resin (A-3)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 490 parts by mass of polytetramethylene glycol (number average molecular weight; 1,000), 5.7 parts by mass of 2-hydroxyethyl acrylate, 2, 2 parts by mass of 6-di-tert-butyl-cresol and 0.3 parts by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 105 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-3). The obtained urethane acrylate resin (A-3) had an acryloyl group equivalent of 12,235 and a weight average molecular weight of 28,000.

[Synthesis Example 4]
<Synthesis of urethane acrylate resin (A-4)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 498 parts by mass of polytetramethylene glycol (number average molecular weight; 1,000), 4.9 parts by mass of 2-hydroxyethyl acrylate, 2, 2 parts by mass of 6-di-tert-butyl-cresol and 0.3 parts by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 105 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-4). The obtained urethane acrylate resin (A-4) had an acryloyl group equivalent of 14,404 and a weight average molecular weight of 28,000.

[Synthesis Example 5]
<Synthesis of urethane acrylate resin (A-5)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 508 parts by mass of polytetramethylene glycol (number average molecular weight; 1,000), 4.9 parts by mass of 2-hydroxyethyl acrylate, 2, 2 parts by mass of 6-di-tert-butyl-cresol and 0.3 parts by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 106 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-5). The obtained urethane acrylate resin (A-5) had an acryloyl group equivalent of 14,664 and a weight average molecular weight of 30,000.

[Comparative Synthesis Example 1]
<Synthesis of urethane acrylate resin (A-6)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 470 parts by mass of polytetramethylene glycol (number average molecular weight; 1,000), 9.5 parts by mass of 2-hydroxyethyl acrylate, 2, 2 parts by mass of 6-di-tert-butyl-cresol and 0.3 parts by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 102 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-6). The obtained urethane acrylate resin (A-6) had an acryloyl group equivalent of 7,107 and a weight average molecular weight of 19,000.

[Comparative Synthesis Example 2]
<Synthesis of urethane acrylate resin (A-7)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 493 parts by mass of polytetramethylene glycol (number average molecular weight; 1,000), 3.8 parts by mass of 2-hydroxyethyl acrylate, 2, 2 parts by mass of 6-di-tert-butyl-cresol and 0.3 parts by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 105 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-7). The obtained urethane acrylate resin (A-7) had an acryloyl group equivalent of 18,387 and a weight average molecular weight of 29,000.

[Comparative Synthesis Example 3]
<Synthesis of urethane acrylate resin (A-8)>
Polycarbonate polyol (obtained by reacting a polyol containing 1,5-pentanediol and 1,6-hexanediol with a dialkyl carbonate in a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer. 456 parts by mass of polycarbonate polyol, number average molecular weight; 1,000), 9.5 parts by mass of 2-hydroxyethyl acrylate, 2 parts by mass of 2,6-ditertiarybutyl-cresol, p-methoxyphenol 0.3 Part by weight was added. After raising the temperature in the reaction vessel to 40 ° C., 102 parts by mass of isophorone diisocyanate was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane acrylate resin (A-8). The obtained urethane acrylate resin (A-8) had an acryloyl group equivalent of 6,935 and a weight average molecular weight of 20,000.

[Example 1]
In a container equipped with a stirrer, a reflux condenser, and a thermometer, 100 parts by mass of the urethane acrylate resin (A-1) synthesized by the above-described method, 65 parts by mass of butyl acrylate, and 45 parts by mass of dimethylacrylamide were heated at 80 ° C. And stirred until uniform. Thereafter, the mixture was cooled to room temperature, and 3 parts by mass of 2,4,6-trimethylbenzoyldiphenylphosphine oxide was added with stirring, followed by stirring until uniform. Thereafter, the mixture was filtered through a 200 mesh wire mesh to obtain an ultraviolet curable adhesive resin composition.

[Examples 2 to 6, Comparative Example 1]
Except for changing the type of urethane acrylate resin to be used, the type and amount of (meth) acrylic monomer, the type and amount of photopolymerization initiator, and the type and amount of other additives as shown in Tables 1-2, In the same manner as in Example 1, an ultraviolet curable adhesive resin composition was obtained.

[Method for measuring weight average molecular weight]
The weight average molecular weights of the polyol and urethane acrylate resin used in Examples and / or Comparative Examples were measured by gel permeation chromatography (GPC) method under the following conditions.

Measuring device: High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation)
Column: The following columns manufactured by Tosoh Corporation were connected in series.
"TSKgel G5000" (7.8 mm ID x 30 cm) x 1 "TSKgel G4000" (7.8 mm ID x 30 cm) x 1 "TSKgel G3000" (7.8 mm ID x 30 cm) x 1 “TSKgel G2000” (7.8 mm ID × 30 cm) × 1 detector: RI (differential refractometer)
Column temperature: 40 ° C
Eluent: Tetrahydrofuran (THF)
Flow rate: 1.0 mL / min Injection amount: 100 μL (tetrahydrofuran solution with a sample concentration of 0.4 mass%)
Standard sample: A calibration curve was prepared using the following standard polystyrene.

(Standard polystyrene)
"TSKgel standard polystyrene A-500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-1000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-2500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-5000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-1" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-2" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-4" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-10" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-20" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-40" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-80" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-128" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-288" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-550" manufactured by Tosoh Corporation

[Method for producing adhesive film]
For UV curable adhesives obtained in Examples and Comparative Examples so that the film thickness after UV irradiation is 175 μm on the surface of a 50 μm-thick polyethylene terephthalate film (release PET 50) whose surface has been subjected to mold release treatment The resin composition was applied, and release PET50 was bonded. Thereafter, UV irradiation was performed with a UV irradiation apparatus so that the integrated light quantity of the wavelength in the UV-A region after passing through the release PET 50 was 1 J / cm ² , thereby producing an adhesive film.

[Measurement method of adhesive strength]
One side of the pressure-sensitive adhesive film prepared by the above-described method was bonded to a 75 μm-thick polyethylene terephthalate film (PET75), and a pressure-sensitive adhesive film having a PET75 substrate bonded to one side was prepared. What cut this into 25 mm width was made into the test piece. The test piece was attached to a glass plate and a polycarbonate (PC) plate, which are adherends, by 2 kg rolls × 2 reciprocations. One hour after pasting, the 180 ° peel strength was measured in an atmosphere of 23 ° C. and 50% RH to obtain adhesive strength.

[Method of measuring holding force]
A test piece prepared in the same manner as the test piece used in the method for measuring the adhesive strength was laminated on a mirror-finished stainless steel plate so that the adhesion area was 25 mm × 25 mm, and the atmosphere was 23 ° C. and 50% RH. They were pasted together by reciprocating 2 kg rolls twice.
Next, under an atmosphere of 70 ° C., a load of 500 g is applied to the test piece attached to the stainless steel plate in a 0 ° direction (shear direction) with respect to the stainless steel plate until the test piece slips off the stainless steel plate. Was measured and the holding time was defined as holding power.

[Measurement method of step following ability]
One side of the pressure-sensitive adhesive film prepared by the above-described method was bonded to a polyethylene terephthalate film (PET100) having a thickness of 100 μm, and a pressure-sensitive adhesive film having a PET100 substrate bonded to one side was prepared. A test piece was cut into 50 mm length and 40 mm width. Next, a frame having a thickness of 50 μm, a length of 40 mm, a width of 30 mm, and a width of 5 mm was printed on 100 μm of PET to create a 50 μm step. From the printed frame, the above-mentioned test piece was attached in a 2 kg roll × 2 reciprocation. This was autoclaved for 20 minutes at a pressure of 0.5 MPa in a 50 ° C. atmosphere. Then, it was left in an 80 ° C. atmosphere for 24 hours, and the inner part of the 50 μm thick frame was visually observed to evaluate the followability to a 50 μm thick step.
◎: No bubbles mixed ○: Some bubbles are observed ×: Many bubbles are mixed

[Measurement method of whitening resistance]
One side of the pressure-sensitive adhesive film prepared by the above-described method was bonded to a polyethylene terephthalate film (PET100) having a thickness of 100 μm, and a pressure-sensitive adhesive film having a PET100 substrate bonded to one side was prepared. This was cut into a length of 50 mm and a width of 40 mm, and a test piece was affixed to a slide glass by a 2 kg roll × 2 reciprocation. The haze was measured for the test piece with a turbidimeter “NDH5000” (manufactured by Nippon Denshoku Industries Co., Ltd.) according to JIS K 7361-1, and this value was used as an initial value. Next, this test piece was left at 85 ° C. × 85% RH in an atmosphere for 100 hours and then taken out. After taking out, 10 minutes, 1 hour and 3 hours, the haze was measured with a turbidimeter “NDH5000” (Nippon Denshoku Industries Co., Ltd.). )) And measured according to JIS K 7361-1.

[Measurement method of wet heat resistance]
One side of the pressure-sensitive adhesive film prepared by the above-described method was bonded to a 75 μm-thick polyethylene terephthalate film (PET75), and a pressure-sensitive adhesive film having a PET75 substrate bonded to one side was prepared. What cut this into 25 mm width was made into the test piece. Moreover, the adherend was a glass plate (JIS R 3202) and was attached to the adherend by 2 kg roll × 2 reciprocation. This was left in an atmosphere of 60 ° C. × 90% RH and 85 ° C. × 85% RH for 250 hours. Then, it was left for 24 hours in an atmosphere of 23 ° C. × 50% RH, and the 180-degree peel strength was measured in the same atmosphere to determine the adhesive strength after wet heat.

The translated words in Tables 1 and 2 will be described.
BA; butyl acrylate 2EHA; 2-ethylhexyl acrylate ACMO; acryloylmorpholine DMAA; dimethylacrylamide CHA; cyclohexyl C-1; 2,4,6-trimethylbenzoyldiphenylphosphine oxide C-2; 2-hydroxy 2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone KBM-403; 3-glycidoxypropylmethyldiethoxysilane

  It was found that the pressure-sensitive adhesive obtained using the ultraviolet curable pressure-sensitive adhesive resin composition of the present invention was excellent in adhesive strength and step following ability.

  Moreover, although Examples 2-8 are the aspects which used the silane coupling agent further, it turned out that it is excellent also in heat-and-moisture resistance.

  On the other hand, although the comparative example 1 is an aspect using the urethane acrylate whose acryloyl group equivalent is 7,107, it turned out that level | step difference followability is unsatisfactory.

  Moreover, although the comparative example 2 is an aspect using the urethane acrylate whose equivalent of an acryloyl group is 18,387, it turned out that the cohesive force of an adhesive is insufficient and its holding power is unsatisfactory.

  Moreover, although the comparative example 3 is an aspect using what does not have a nitrogen atom as a urethane acrylate and the (meth) acryl monomer whose equivalent of an acryloyl group is 6,935, step difference followability is bad. It was also found that the whitening resistance was remarkably poor.

Claims (6)

Urethane (meth) acrylate resin (A), (meth) acrylic monomer (B) obtained by reacting polyol (a), polyisocyanate (b) and (meth) acrylic compound (c) having a hydroxyl group, and A resin composition for an ultraviolet curable pressure-sensitive adhesive containing a photopolymerization initiator (C), wherein the equivalent of the (meth) acryloyl group of the urethane (meth) acrylate resin (A) is 8,000 to 17,000. range der of is, and the (meth) acrylic monomer (B), the glass transition temperature is capable of forming a homopolymer of 15 ℃ or less (meth) one or more acrylic monomers (B-1) , the glass transition temperature has a form available nitrogen higher than 15 ℃ homopolymer (meth) UV curable a mixture der wherein Rukoto with one or more acrylic monomers (B-2) adhesive Resin Narubutsu. The mass ratio [(B-1) / (B-2)] of the (meth) acrylic monomer (B-1) and the (meth) acrylic monomer (B-2) is 90/10 to 10/10. in the range of 10/90 claim 1 UV curable adhesive resin composition. The (meth) acrylic monomer (B-1) is methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, 2-methoxyethyl acrylate, 2-hydroxyethyl acrylate, and acrylic acid 4 The resin composition for an ultraviolet curable pressure-sensitive adhesive according to claim 1 , wherein the resin composition is one or more selected from the group consisting of -hydroxybutyl. The resin composition for an ultraviolet curable adhesive according to claim 1, further comprising a silane coupling agent (D). The resin composition for an ultraviolet curable adhesive according to claim 4, wherein the silane coupling agent (D) is a silane coupling agent having an epoxy group and / or a silane coupling agent having an alicyclic epoxy group. A pressure-sensitive adhesive obtained by using the resin composition for an ultraviolet curable pressure-sensitive adhesive according to any one of claims 1 to 5 .