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WO2016013510A1 - Composition adhésive sensible à la pression durcissable par rayonnement d'énergie active, adhésif sensible à la pression et feuille adhésive sensible à la pression l'utilisant - Google Patents

Composition adhésive sensible à la pression durcissable par rayonnement d'énergie active, adhésif sensible à la pression et feuille adhésive sensible à la pression l'utilisant Download PDF

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Publication number
WO2016013510A1
WO2016013510A1 PCT/JP2015/070536 JP2015070536W WO2016013510A1 WO 2016013510 A1 WO2016013510 A1 WO 2016013510A1 JP 2015070536 W JP2015070536 W JP 2015070536W WO 2016013510 A1 WO2016013510 A1 WO 2016013510A1
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Prior art keywords
meth
acrylate
sensitive adhesive
compound
active energy
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PCT/JP2015/070536
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English (en)
Japanese (ja)
Inventor
亮輔 谷口
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Mitsubishi Chemical Corp
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Nippon Synthetic Chemical Industry Co Ltd
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Priority to KR1020177003309A priority Critical patent/KR102245657B1/ko
Priority to JP2015535913A priority patent/JP6610256B2/ja
Priority to CN201580039727.3A priority patent/CN106536653B/zh
Publication of WO2016013510A1 publication Critical patent/WO2016013510A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils

Definitions

  • the present invention relates to an active energy ray-curable pressure-sensitive adhesive composition containing a urethane (meth) acrylate compound, a pressure-sensitive adhesive using the same, and a pressure-sensitive adhesive sheet.
  • adhesives such as strong adhesives for the purpose of firmly bonding adherends for a long period of time, and peel-off type adhesives that are supposed to be peeled off from adherends after being attached.
  • strong adhesives for the purpose of firmly bonding adherends for a long period of time
  • peel-off type adhesives that are supposed to be peeled off from adherends after being attached.
  • types, and the most suitable adhesive is designed and used for each field.
  • an ultraviolet curable adhesive resin composition containing a urethane (meth) acrylate resin is excellent in the balance between the adhesive force and the holding force to a substrate. It is disclosed.
  • the resin composition for pressure-sensitive adhesives of Patent Document 1 is difficult to say that the adhesive strength is sufficient. Although this resin composition for pressure-sensitive adhesives has achieved good heat-resistant yellowing, this effect is achieved by adding additives such as stabilizers and antioxidants. The performance of the heat-and-moisture resistance was not improved by the agent resin composition itself.
  • the present invention has an object of providing a pressure-sensitive adhesive composition for obtaining a pressure-sensitive adhesive having a good balance between adhesive strength and heat-and-moisture resistance in such a background.
  • the present inventor has conducted extensive research in view of such circumstances, and as a result, in the active energy ray-curable pressure-sensitive adhesive composition containing a urethane (meth) acrylate compound having a relatively high molecular weight and an ethylenically unsaturated monomer,
  • an active energy ray-curable pressure-sensitive adhesive composition containing a heterocyclic ring-containing monomer (b1) and a hydroxyl group-containing monomer (b2) in a predetermined content ratio as an ethylenically unsaturated monomer the adhesive force and heat and moisture resistance are balanced.
  • the present inventors have found that an excellent pressure-sensitive adhesive can be obtained and completed the present invention.
  • the gist of the present invention is that a polyvalent isocyanate compound (a1), a hydroxyl group-containing (meth) acrylate compound (a2), and a polyol compound (a3) are reacted, and the weight average molecular weight is 20,000 to 120.
  • An active energy ray-curable pressure-sensitive adhesive containing a urethane (meth) acrylate compound (A) and an ethylenically unsaturated monomer (B) (excluding the urethane (meth) acrylate compound (A)).
  • a composition comprising a heterocyclic ring-containing monomer (b1) and a hydroxyl group-containing monomer (b2) as the ethylenically unsaturated monomer (B), and containing the heterocyclic ring-containing monomer (b1) and the hydroxyl group-containing monomer (b2)
  • this invention has an adhesive layer formed by hardening
  • An adhesive sheet is also provided.
  • the pressure-sensitive adhesive and heat-and-moisture resistance are well-balanced, that is, exhibits high adhesive strength and does not deteriorate transparency even when exposed to wet heat conditions.
  • a pressure-sensitive adhesive can be obtained, and this pressure-sensitive adhesive is useful, for example, as a pressure-sensitive adhesive used for an optical device such as an optical device such as a touch panel or an optical recording medium. The reason why such an effect is obtained is not clear, but it is thought that the use of the urethane (meth) acrylate compound (A) having a relatively high molecular weight improves the adhesive strength by increasing the flexibility of the pressure-sensitive adhesive layer. It is done.
  • the balance between cohesion and hydrophilicity can be controlled, and adhesive strength It is considered that an adhesive having a good balance between moisture and heat resistance can be obtained.
  • (meth) acrylic acid is acrylic acid or methacrylic acid
  • (meth) acryl is acrylic or methacrylic
  • (meth) acryloyl is acryloyl or methacryloyl
  • (meth) acrylate is acrylate or Each means methacrylate.
  • the acrylic resin is a resin obtained by polymerizing a polymerization component containing at least one (meth) acrylate monomer.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention contains a urethane (meth) acrylate compound (A) and an ethylenically unsaturated monomer (B).
  • the urethane (meth) acrylate compound (A) used in the present invention is obtained by reacting a polyvalent isocyanate compound (a1), a hydroxyl group-containing (meth) acrylate compound (a2), and a polyol compound (a3). It is.
  • polyvalent isocyanate compound (a1) examples include aromatics such as tolylene diisocyanate, diphenylmethane diisocyanate, polyphenylmethane polyisocyanate, modified diphenylmethane diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, phenylene diisocyanate, and naphthalene diisocyanate.
  • Polyisocyanates such as pentamethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate; alicyclic diisocyanates (eg, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated) Xylylene diisocyanate Alicyclic polyisocyanates norbornene diisocyanate), etc., or a trimer compound or multimeric compounds of these polyisocyanates; allophanate type polyisocyanate, buret type polyisocyanate, and the like. These can be used alone or in combination of two or more.
  • aliphatic diisocyanates such as pentamethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate; hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, isophorone diisocyanate, norbornene
  • An alicyclic diisocyanate such as diisocyanate is preferably used, and particularly preferably, an alicyclic diisocyanate (particularly isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate) is used in terms of small curing shrinkage. More preferably, in terms of excellent reactivity and versatility, hydrogenated xylylene diisocyanate and isophorone diisocyanate are used. It is needed.
  • Examples of the hydroxyl group-containing (meth) acrylate compound (a2) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) ) Acrylates, hydroxyalkyl (meth) acrylates such as 6-hydroxyhexyl (meth) acrylate; 2-hydroxyethylacryloyl phosphate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, caprolactone-modified 2-hydroxyethyl ( (Meth) acrylate, dipropylene glycol (meth) acrylate, fatty acid modified-glycidyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono ( Acrylate), 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, glycerin di (
  • a hydroxyl group-containing (meth) acrylate compound having one ethylenically unsaturated group is preferable in terms of excellent flexibility of the pressure-sensitive adhesive layer, more preferably 2-hydroxyethyl (meth) acrylate, 2-hydroxy Hydroxyalkyl (meth) acrylates such as hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and in particular 2-hydroxyethyl Use of (meth) acrylate or 4-hydroxybutyl (meth) acrylate is preferable in terms of excellent reactivity and versatility.
  • polyol compound (a3) examples include polyether polyols, polyester polyols, polycarbonate polyols, polyolefin polyols, (meth) acrylic polyols, polysiloxane polyols, and the like.
  • polyether polyols examples include polyether polyols containing alkylene structures such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polybutylene glycol, and polyhexamethylene glycol, and random or block copolymers of these polyalkylene glycols. Is mentioned.
  • polyester-based polyol examples include three types of components: a polycondensation product of a polyhydric alcohol and a polycarboxylic acid, a ring-opening polymer of a cyclic ester (lactone), a polyhydric alcohol, a polycarboxylic acid, and a cyclic ester. And reactants.
  • polyhydric alcohol examples include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, 1,4-tetramethylene diol, 1,3-tetramethylene diol, 2-methyl-1,3-trimethyl.
  • Methylene diol 1,5-pentamethylene diol, neopentyl glycol, 1,6-hexamethylene diol, 3-methyl-1,5-pentamethylene diol, 2,4-diethyl-1,5-pentamethylene diol, glycerin , Trimethylolpropane, trimethylolethane, cyclohexanediols (such as 1,4-cyclohexanediol), bisphenols (such as bisphenol A), sugar alcohols (such as xylitol and sorbitol)
  • polyvalent carboxylic acid examples include aliphatic dicarboxylic acids such as malonic acid, maleic acid, fumaric acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, and dodecanedioic acid; -Alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, orthophthalic acid, 2,6-naphthalenedicarboxylic acid, paraphenylenedicarboxylic acid, trimellitic acid, and the like.
  • aliphatic dicarboxylic acids such as malonic acid, maleic acid, fumaric acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, and dodecanedioic acid
  • -Alicyclic dicarboxylic acids such as
  • cyclic ester examples include propiolactone, ⁇ -methyl- ⁇ -valerolactone, and ⁇ -caprolactone.
  • polycarbonate polyol examples include a reaction product of a polyhydric alcohol and phosgene, a ring-opening polymer of a cyclic carbonate (alkylene carbonate, etc.), and the like.
  • polyhydric alcohol examples include polyhydric alcohols exemplified in the description of the polyester-based polyol, and examples of the alkylene carbonate include ethylene carbonate, trimethylene carbonate, tetramethylene carbonate, hexamethylene carbonate, and the like. It is done.
  • the polycarbonate polyol may be a compound having a carbonate bond in the molecule and having a terminal hydroxyl group, and may have an ester bond together with the carbonate bond.
  • polyolefin-based polyol examples include those having a saturated hydrocarbon skeleton having a homopolymer or copolymer such as ethylene, propylene and butene, and having a hydroxyl group at the molecular end.
  • polyisoprene polyol, polybutadiene polyol, nitrile butadiene polyol, styrene butadiene polyol, and the like can be given.
  • the polyolefin-based polyol may be a hydrogenated polyolefin-based polyol in which all or part of the ethylenically unsaturated groups contained in the structure is hydrogenated.
  • Examples of the (meth) acrylic polyol include those having at least two hydroxyl groups in the polymer or copolymer molecule of (meth) acrylic acid ester.
  • (meth) acrylic acid ester , For example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, (meth) acrylic acid And (meth) acrylic acid alkyl esters such as 2-ethylhexyl, decyl (meth) acrylate, dodecyl (meth) acrylate, and octadecyl (meth) acrylate.
  • polysiloxane polyol examples include dimethyl polysiloxane polyol and methylphenyl polysiloxane polyol.
  • polyester-based polyols and polyether-based polyols are preferable, and polyester-based polyols are particularly preferable from the viewpoint of versatility.
  • the number of hydroxyl groups contained in the polyol compound (a3) is preferably 2 to 5, particularly preferably 2 to 3, and more preferably 2. If the number of hydroxyl groups is too large, gelation tends to occur during the reaction.
  • the polyol compound (a3) preferably has a weight average molecular weight of 1,000 to 20,000, particularly preferably 2,000 to 18,000, more preferably 3,000 to 16,000. is there. If the weight average molecular weight is too small, the adhesive strength of the pressure-sensitive adhesive layer tends to be reduced, and if it is too large, the reactivity with the polyvalent isocyanate compound (a1) tends to be reduced.
  • the above-mentioned weight average molecular weight is a weight average molecular weight in terms of standard polystyrene molecular weight, and the column: Shodex GPC KF-806L (excluded) was subjected to high performance liquid chromatography (“Shodex GPC system-11” manufactured by Showa Denko KK). Limit molecular weight: 2 ⁇ 10 7 , separation range: 100 to 2 ⁇ 10 7 , theoretical plate number: 10,000 plate / piece, filler material: styrene-divinylbenzene copolymer, filler particle size: 10 ⁇ m) Measured by using series.
  • the hydroxyl value of the polyol compound (a3) is preferably 10 to 300 mgKOH / g, particularly preferably 15 to 150 mgKOH / g, and more preferably 20 to 120 mgKOH / g. If the hydroxyl value is too high, the urethane (meth) acrylate compound (A) tends to have a low molecular weight and the adhesive strength tends to decrease, and if it is too low, the viscosity tends to increase and the workability tends to decrease.
  • the urethane (meth) acrylate compound (A) can be produced as follows. For example, (1) A method in which the above polyisocyanate compound (a1), a hydroxyl group-containing (meth) acrylate compound (a2), and a polyol compound (a3) are charged in a reactor or separately and reacted (2) ) A method of reacting a hydroxyl group-containing (meth) acrylate compound (a2) with a reaction product obtained by reacting the polyvalent isocyanate compound (a1) and the polyol compound (a3) in advance.
  • the method (2) is preferable from the viewpoint of reaction stability and reduction of by-products.
  • the reaction between the polyvalent isocyanate compound (a1) and the polyol compound (a3) known reaction means can be used.
  • the molar ratio of the isocyanate group in the polyvalent isocyanate compound (a1) to the hydroxyl group in the polyol compound (a3) is usually about 2n: (2n-2) (n is an integer of 2 or more).
  • n is an integer of 2 or more.
  • the addition reaction of the reaction product obtained by reacting the polyvalent isocyanate compound (a1) and the polyol compound (a3) in advance with the hydroxyl group-containing (meth) acrylate compound (a2) is also a known reaction. Means can be used.
  • the reaction molar ratio between the reaction product and the hydroxyl group-containing (meth) acrylate compound (a2) is, for example, that the polyisocyanate compound (a1) has two isocyanate groups and the hydroxyl group-containing (meth) acrylate compound (a2).
  • ) Has one hydroxyl group
  • the reaction product: hydroxyl group-containing (meth) acrylate compound (a2) is about 1: 2
  • the polyisocyanate compound (a1) has three isocyanate groups.
  • the reaction product: hydroxyl group-containing (meth) acrylate compound (a2) is about 1: 3.
  • reaction In the addition reaction between the reaction product and the hydroxyl group-containing (meth) acrylate compound (a2), the reaction is terminated when the residual isocyanate group content in the reaction system is 0.2% by weight or less. A (meth) acrylate compound (A) is obtained.
  • a catalyst is used for the purpose of promoting the reaction. It is also preferable to use.
  • catalysts include dibutyltin dilaurate, dibutyltin diacetate, trimethyltin hydroxide, tetra-n-butyltin, bisacetylacetonate zinc, zirconium tris (acetylacetonate) ethylacetoacetate, zirconium tetraacetylacetonate.
  • Organometallic compounds such as tin octenoate, zinc hexanoate, zinc octenoate, zinc stearate, zirconium 2-ethylhexanoate, cobalt naphthenate, stannous chloride, stannic chloride, potassium acetate and the like; Triethylamine, triethylenediamine, benzyldiethylamine, 1,4-diazabicyclo [2,2,2] octane, 1,8-diazabicyclo [5,4,0] undecene, N, N, N ′, N′-tetramethyl-1 , 3-Butanediamine, N-me Amine-based catalysts such as morpholine and N-ethylmorpholine; bismuth nitrate, bismuth bromide, bismuth iodide, bismuth sulfide, etc., organic bismuth compounds such as dibutyl bismuth dilaurate and dio
  • an isocyanate group is optionally selected.
  • an organic solvent having no functional group that reacts with for example, esters such as ethyl acetate and butyl acetate, ketones such as methyl ethyl ketone and methyl isobutyl ketone, and aromatic solvents such as toluene and xylene Also good.
  • the reaction temperature is usually 30 to 90 ° C., preferably 40 to 80 ° C.
  • the reaction time is usually 2 to 10 hours, preferably 3 to 8 hours.
  • the urethane (meth) acrylate compound (A) In the production of the urethane (meth) acrylate compound (A) by reacting the polyvalent isocyanate compound (a1), the hydroxyl group-containing (meth) acrylate compound (a2), and the polyol compound (a3), it will be described later.
  • the ethylenically unsaturated monomer (B) may be present in the reaction system to prepare a mixture of the urethane (meth) acrylate compound (A) and the ethylenically unsaturated monomer (B).
  • a reaction product obtained by reacting a polyvalent isocyanate compound (a1) and a polyol compound (a3) in advance is reacted with a hydroxyl group-containing (meth) acrylate compound (a2) to obtain urethane (meth) acrylate.
  • the ethylenically unsaturated monomer (B) may be present in the reaction system.
  • the weight average molecular weight of the urethane (meth) acrylate compound (A) is 20,000 to 120,000, preferably 21,000 to 100,000, particularly preferably 22,000 to 90,000, More preferably, it is 25,000-80,000. If the weight average molecular weight is too low, the adhesive strength of the pressure-sensitive adhesive layer tends to decrease, and if it is too high, the viscosity of the urethane (meth) acrylate compound (A) tends to be too high and handling tends to be difficult.
  • the above-mentioned weight average molecular weight is a weight average molecular weight in terms of standard polystyrene molecular weight, and the column: Shodex GPC KF-806L (excluded) was subjected to high performance liquid chromatography (“Shodex GPC system-11” manufactured by Showa Denko KK). Limit molecular weight: 2 ⁇ 10 7 , separation range: 100 to 2 ⁇ 10 7 , theoretical plate number: 10,000 plate / piece, filler material: styrene-divinylbenzene copolymer, filler particle size: 10 ⁇ m) Measured by using series.
  • the viscosity of the urethane (meth) acrylate compound (A) is preferably 1,000 to 1,000,000 mPa ⁇ s, particularly preferably 2,000 to 800,000 mPa as the viscosity at 60 ° C. S, more preferably 3,000 to 600,000 mPa ⁇ s. If the viscosity is too high, handling tends to be difficult, and if it is too low, control of the film thickness tends to be difficult during coating. In addition, the measuring method of a viscosity is based on an E-type viscometer.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention comprises an ethylenically unsaturated monomer (B) (excluding the urethane (meth) acrylate compound (A)) (hereinafter referred to as “ethylenically unsaturated monomer (B). ) "), The heterocyclic-containing monomer (b1) and the hydroxyl group-containing monomer (b2).
  • heterocyclic ring-containing monomer (b1) examples include (meth) acryloylmorpholine, tetramethylpiperidinyl (meth) acrylate, pentamethylpiperidinyl (meth) acrylate, maleimide (meth) acrylate, and isocyanuric acid ethylene oxide modified diester.
  • Heterocycle-containing monomers having nitrogen atoms such as (meth) acrylate, isocyanuric acid ethylene oxide modified tri (meth) acrylate, N-vinylpyrrolidone, 2-vinylpyridine; glycidyl (meth) acrylate, 3-ethyl-3-oxetanylmethyl (Meth) acrylate, furfuryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl) methyl (meth) acrylate, cyclohexane Heterocyclic-containing monomers having an oxygen atom, such as pyro-2- (1,3-dioxolan-4-yl) methyl (meth) acrylate, ⁇ -butyrolactone (meth) acrylate, trimethylolpropane (formal) (meth) acrylate; Examples thereof include heterocycle
  • the heterocyclic-containing monomer (b1) having one ethylenically unsaturated group is preferable in terms of excellent flexibility of the pressure-sensitive adhesive layer, and more preferably has one ethylenically unsaturated group and has a nitrogen atom.
  • a heterocyclic ring-containing monomer is preferable in that the cohesive force of the pressure-sensitive adhesive layer is excellent, and (meth) acryloylmorpholine is particularly preferable.
  • these can be used individually by 1 type or in combination of 2 or more types.
  • the heterocyclic-containing monomer (b1) may be contained in the synthesized urethane (meth) acrylate compound (A) or urethane (meth). You may use as a diluent in the synthesis reaction of an acrylate type compound (A). In order to suppress an increase in viscosity, the heterocyclic ring-containing monomer (b1) is preferably used as a diluent during the synthesis reaction of the urethane (meth) acrylate compound (A).
  • hydroxyl group-containing monomer (b2) examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 6-hydroxy.
  • Hydroxyalkyl (meth) acrylates such as hexyl (meth) acrylate, 2-hydroxyethylacryloyl phosphate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, dipropylene Glycol (meth) acrylate, fatty acid modified-glycidyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, 2 Hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, glycerol mono (meth) acrylate, glycerol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate Diglycidyl phthalate di (meth)
  • a hydroxyl group (meth) acrylate compound having one ethylenically unsaturated group is preferable in terms of excellent flexibility of the pressure-sensitive adhesive layer.
  • 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl ( Hydroxyalkyl (meth) acrylates such as (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate and the like are preferable in view of excellent versatility, particularly 4 -Hydroxybutyl (meth) acrylate is preferably used because the adhesive layer has high adhesive strength and low skin irritation. Moreover, these can be used individually by 1 type or in combination of 2 or more types.
  • the hydroxyl group-containing monomer (b2) may be contained in the synthesized urethane (meth) acrylate compound (A) or urethane (meth) acrylate.
  • the hydroxyl group-containing (meth) acrylate (a3) may also be used as a diluent during the synthesis reaction of the compound (A).
  • the ratio of the heterocyclic ring-containing monomer (b1) to the hydroxyl group-containing monomer (b2) is too large, the coating film becomes hard and the adhesive strength of the pressure-sensitive adhesive layer tends to decrease, and the heterocyclic ring-containing monomer with respect to the hydroxyl group-containing monomer (b2)
  • the ratio of (b1) is too small, the adhesive force of the pressure-sensitive adhesive layer is lowered due to insufficient cohesive force, and the viscosity at the time of production tends to be too high, making the production difficult.
  • ethylenically unsaturated monomer (B) in addition to the heterocyclic ring-containing monomer (b1) and the hydroxyl group-containing monomer (b2), other monomers (b3) such as monofunctional monomers, bifunctional monomers, and trifunctional or higher monomers are included. It may be.
  • Such monofunctional monomers include styrene monomers such as styrene, vinyl toluene, chlorostyrene, ⁇ -methylstyrene, methyl (meth) acrylate, ethyl (meth) acrylate, acrylonitrile, 2-methoxyethyl (meth) acrylate, Phenoxyethyl (meth) acrylate, lauryl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) Acrylate, dicyclopentanyl (meth) acrylate, n-butyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl
  • bifunctional monomers examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, and di Propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified bisphenol A type di (meth) acrylate, propylene oxide modified bisphenol A Type di (meth) acrylate, cyclohexanedimethanol di (meth) acrylate, ethoxylated cyclohexanedimethanol di ( Data) acrylate, dimethylol dicyclopentane di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, 1,6
  • tri- or higher functional monomer examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tri (meth) acryloyloxyethoxytrimethylolpropane, and glycerin poly.
  • a Michael adduct of acrylic acid or 2-acryloyloxyethyl dicarboxylic acid monoester can be used in combination.
  • examples of such a Michael adduct of acrylic acid include acrylic acid dimer, methacrylic acid dimer, acrylic trimer, and methacrylic acid.
  • a trimer, an acrylic acid tetramer, a methacrylic acid tetramer, etc. are mentioned.
  • the above-mentioned 2-acryloyloxyethyl dicarboxylic acid monoester is a carboxylic acid having a specific substituent, such as 2-acryloyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, 2-acryloyloxy Examples include ethyl phthalic acid monoester, 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl hexahydrophthalic acid monoester, 2-methacryloyloxyethyl hexahydrophthalic acid monoester, and the like. Furthermore, other oligoester acrylates can also be mentioned.
  • the other in the ethylenically unsaturated monomer (B) is not particularly limited, but is usually 30% by weight or less, preferably 25% by weight or less, particularly preferably 20% by weight or less.
  • the amount of the ethylenically unsaturated monomer (B) is too large relative to the urethane (meth) acrylate compound (A)
  • the viscosity of the pressure-sensitive adhesive composition tends to be too low, and thick coating tends to be difficult.
  • the viscosity of the pressure-sensitive adhesive composition tends to be too high, making it difficult to handle.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention is obtained.
  • the active energy ray-curable pressure-sensitive adhesive composition further contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited as long as it generates radicals by the action of light.
  • auxiliary agents for these photopolymerization initiators include triethanolamine, triisopropanolamine, 4,4′-dimethylaminobenzophenone (Michler ketone), 4,4′-diethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid, Ethyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate (n-butoxy), isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,4-diethylthioxanthone, 2, 4-diisopropylthioxanthone or the like can be used in combination. These auxiliaries can be used alone or in combination of two or more.
  • the content of the photopolymerization initiator is preferably 1 to 10 parts by weight with respect to 100 parts by weight as a total of the urethane (meth) acrylate compound (A) and the ethylenically unsaturated monomer (B). Particularly preferred is 2 to 5 parts by weight. If the content is too small, the curing rate tends to decrease. If the content is too large, the curability does not improve and the economy tends to decrease.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention includes an antioxidant, a flame retardant, It is also possible to contain an antistatic agent, a filler, a leveling agent, a stabilizer, a reinforcing agent, a matting agent and the like.
  • an antioxidant e.g., a sulfur dioxide, a carbonate, a carbonate, a carbonate, and the like.
  • an antistatic agent e.g., a filler, a leveling agent, a stabilizer, a reinforcing agent, a matting agent and the like.
  • the crosslinking agent a compound having an action of causing crosslinking by heat, specifically, an epoxy compound, an aziricin compound, a melamine compound, an isocyanate compound, a chelate compound, and the like can be used.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention can contain a polythiol compound from the viewpoint of suppressing unreacted components and improving adhesive strength.
  • the polythiol compound is not particularly limited, but a compound having 2 to 6 mercapto groups in the molecule is preferable.
  • aliphatic polythiols such as alkanedithiol having about 2 to 20 carbon atoms, and aromatics such as xylylenedithiol.
  • Polythiols polythiols obtained by replacing halogen atoms of halohydrin adducts of alcohols with mercapto groups, polythiols consisting of hydrogen sulfide reaction products of polyepoxide compounds, polyhydric alcohols having 2 to 6 hydroxyl groups in the molecule And polythiols composed of esterified products with thioglycolic acid, ⁇ -mercaptopropionic acid, or ⁇ -mercaptobutanoic acid, etc., and these can be used alone or in combination of two or more. .
  • the content of the polythiol compound is preferably 0.01 to 10 parts by weight or less with respect to 100 parts by weight in total of the urethane (meth) acrylate compound (A) and the ethylenically unsaturated monomer (B). It is particularly preferably 1 to 5 parts by weight or less.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention includes alcohols such as methanol, ethanol, propanol, n-butanol, and i-butanol, as necessary, to adjust the viscosity at the time of coating; Ketones such as acetone, methyl isobutyl ketone, methyl ethyl ketone, cyclohexanone; cellosolves such as ethyl cellosolve; aromatics such as toluene and xylene; glycol ethers such as propylene glycol monomethyl ether; methyl acetate, ethyl acetate, butyl acetate, etc.
  • alcohols such as methanol, ethanol, propanol, n-butanol, and i-butanol, as necessary, to adjust the viscosity at the time of coating
  • Ketones such as acetone, methyl isobutyl ketone, methyl
  • Acetic esters dilute solvents such as diacetone alcohol may be used, but the solvent remains in the coating film and the cured components may volatilize when dried. Is preferred.
  • the phrase “substantially free of solvent” is usually 1% by weight or less, preferably 0.5% by weight or less, more preferably 0.1% by weight or less based on the entire active energy ray-curable pressure-sensitive adhesive composition. It points to something.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention is usually applied to a base sheet or the like and is a pressure-sensitive adhesive sheet (the pressure-sensitive adhesive sheet is meant to include a pressure-sensitive adhesive film and a pressure-sensitive adhesive tape unless otherwise specified. ) And the like, and after application to a substrate sheet, it is crosslinked by irradiation with active energy rays to form a pressure-sensitive adhesive, thereby exhibiting pressure-sensitive adhesiveness.
  • the base sheet examples include polyester resins such as polyethylene terephthalate and polybutylene terephthalate, polyolefin resins such as polyethylene, polypropylene, and ethylene-propylene copolymer, polycarbonate resins, polyurethane resins, acrylic resins, and polystyrene resins.
  • resin sheets such as resin, ethylene-vinyl acetate copolymer, polyvinyl chloride, polybutene, polybutadiene, polymethylpentene, and acrylonitrile butadiene styrene copolymer (ABS), and glass plates.
  • Various substrate sheets may be subjected to surface treatment such as anchor layer, corona treatment, plasma treatment, and the like.
  • the method for applying the active energy ray-curable pressure-sensitive adhesive composition is not particularly limited. For example, wet coating such as spray, shower, dipping, roll, spin, screen printing, inkjet printing, dispenser, etc. Law.
  • the drying conditions may be set to a drying temperature and a drying time sufficient to volatilize the solvent.
  • the drying temperature is usually 40 to 100. It is preferably 50 ° C. to 90 ° C.
  • the drying time may be a time that allows the solvent in the coating film to be completely volatilized at the time of drying, but is preferably 1 to 60 minutes in view of production suitability.
  • the active energy ray-curable pressure-sensitive adhesive composition of the present invention is applied to a substrate sheet and dried, it is cured (cross-linked) by irradiation with active energy rays to become a pressure-sensitive adhesive, and further a pressure-sensitive adhesive sheet.
  • a separator can be laminated on the surface of the pressure-sensitive adhesive for the purpose of protecting the pressure-sensitive adhesive from contamination until the pressure-sensitive adhesive sheet of the present invention is bonded to an adherend (member).
  • a separator what carried out mold release processing of base materials, such as the resin sheet illustrated above and paper, cloth, and a nonwoven fabric, can be used.
  • the pressure-sensitive adhesive composition on the base sheet usually, as a solution of the active energy ray-curable pressure-sensitive adhesive composition, after adjusting to a viscosity suitable for coating with a solvent, if necessary, Application and drying are performed.
  • a coating method a direct application method in which a solution-like active energy ray-curable pressure-sensitive adhesive composition is directly applied to a substrate sheet, or a solution-like active energy ray-curable pressure-sensitive adhesive composition was applied to a separator. Later, a transfer coating method for bonding to a base sheet is exemplified.
  • an active energy ray-curable pressure-sensitive adhesive composition is applied to a base sheet, dried by heating, and then irradiated with active energy rays, and then a separator is attached, or the active energy is applied to the base sheet.
  • the method include a method in which a linear curable pressure-sensitive adhesive composition is applied and heat-dried, and then a separator is attached, and then an active energy ray is irradiated.
  • the coating is performed by methods such as roll coating, die coating, gravure coating, comma coating, screen printing, and printing coating with a dispenser.
  • the active energy ray-curable pressure-sensitive adhesive composition is applied to the separator, heated and dried, then irradiated with active energy rays, and then the substrate sheet is bonded, or the active energy is applied to the separator.
  • the method include a method in which a linear curable pressure-sensitive adhesive composition is applied and dried by heating, and then a base material sheet is bonded to the active energy ray.
  • the method similar to direct coating can be used.
  • rays such as far ultraviolet rays, ultraviolet rays, near ultraviolet rays, infrared rays, electromagnetic waves such as X rays and ⁇ rays, electron beams, proton rays, neutron rays, etc.
  • Curing by ultraviolet irradiation is advantageous from the standpoint of availability of the device and price.
  • electron beam irradiation it can harden
  • a high pressure mercury lamp that emits light in a wavelength range of 150 to 450 nm
  • an ultrahigh pressure mercury lamp a carbon arc lamp, a metal halide lamp, a xenon lamp, a chemical lamp, an electrodeless discharge lamp, an LED, etc.
  • the irradiation may be about 30 to 3000 mJ / cm 2 .
  • heating can be performed as necessary to complete the curing.
  • the thickness of the pressure-sensitive adhesive layer formed on the base sheet after irradiation with active energy rays is appropriately set depending on the application, but is usually 5 to 300 ⁇ m, preferably 10 to 250 ⁇ m. . If the thickness of the pressure-sensitive adhesive layer is too thin, the adhesive physical properties tend to be difficult to stabilize, and if it is too thick, adhesive residue tends to occur.
  • 2-hydroxyethyl acrylate (a2) 1. 8 g (0.015 mol) was charged and reacted at 60 ° C. for 6 hours. The reaction was terminated when the residual isocyanate group reached 0.3%, and a mixture of urethane (meth) acrylate compound (A-2) (Mw; 35,000) and acryloylmorpholine (b1-1) (urethane ( (Meth) acrylate compound concentration: 80%).
  • Example 4 69 parts of a mixture of the urethane (meth) acrylate resin (A-2) and acryloylmorpholine (b1-1) prepared above (55.2 parts of urethane (meth) acrylate compound (A-2), acryloylmorpholine (b1) -1) 13.8 parts), 31 parts of an ethylenically unsaturated monomer (b2-1), 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan; "Irgacure 184") as a photopolymerization initiator
  • Example 5 69 parts of a mixture of the urethane (meth) acrylate resin (A-3) and acryloylmorpholine (b1-1) produced above (55.2 parts of urethane (meth) acrylate compound (A-3), acryloylmorpholine (b1) -1) 13.8 parts), 31 parts of an ethylenically unsaturated monomer (b2-1), 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan; "Irgacure 184") as a photopolymerization initiator
  • Example 6 69 parts of a mixture of urethane (meth) acrylate resin (A-4) and acryloylmorpholine (b1-1) prepared above (55.2 parts of urethane (meth) acrylate compound (A-4), acryloylmorpholine (b1) -1) 13.8 parts), 31 parts of an ethylenically unsaturated monomer (b2-1), 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan; "Irgacure 184”) as a photopolymerization initiator
  • Example 7 An active energy ray-curable pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that the urethane (meth) acrylate resin (A-1) was changed to the urethane (meth) acrylate resin (A-5). .
  • Example 5 An active energy ray-curable pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that the urethane (meth) acrylate resin (A-1) was changed to the urethane (meth) acrylate resin (A-6). .
  • Example 6 An active energy ray-curable pressure-sensitive adhesive composition was obtained in the same manner as in Example 1, except that the urethane (meth) acrylate resin (A-1) was changed to the urethane (meth) acrylate resin (A-7). .
  • Example 7 An active energy ray-curable pressure-sensitive adhesive composition was obtained in the same manner as in Example 1, except that the ethylenically unsaturated monomer (b2-1) was changed to the ethylenically unsaturated monomer (b3-1).
  • ⁇ Test method> The obtained adhesive sheet for moisture and heat resistance test was cut into 25 mm ⁇ 40 mm, and then pressure-bonded to a glass plate as an adherend to prepare a test piece.
  • the obtained test piece was placed in an environment of 80 ° C. and 90% RH for 100 hours, and b * immediately after the end of the test was measured with a color difference meter to evaluate the moisture and heat resistance (transparency of the pressure-sensitive adhesive layer).
  • the evaluation criteria are as follows. (Evaluation criteria) ⁇ ⁇ ⁇ ⁇ 3 or less ⁇ ⁇ ⁇ ⁇ 3 or more
  • the pressure-sensitive adhesive sheets of Examples 1 to 7 according to the present invention are excellent in balance between adhesive strength and wet heat resistance, and the pressure-sensitive adhesive layers obtained from Examples 1 to 7 are excellent in flexibility.
  • Comparative Examples 1 to 4 in which the content ratio of the heterocyclic ring-containing monomer (b1) and the hydroxyl group-containing monomer (b2) is outside the specified range of the present invention have good wet heat resistance but insufficient adhesive strength. It turns out that it is. Moreover, it turns out that the adhesive layer obtained in Comparative Example 4 is inferior in flexibility.
  • Comparative Example 5 and Comparative Example 6 using a urethane (meth) acrylate-based compound whose weight average molecular weight is lower than the lower limit defined in the present invention have good wet heat resistance, but Comparative Example 5 has insufficient adhesive strength.
  • Comparative Example 6 it can be seen that the adhesive strength was too low to be measured.
  • the adhesive layer obtained from Comparative Example 6 is inferior in flexibility.
  • it replaces with a hydroxyl-containing monomer (b2), and the comparative example 7 using another ethylenically unsaturated monomer (b3) is inadequate in both adhesive force and wet heat resistance.
  • the pressure-sensitive adhesive obtained by curing the active energy ray-curable pressure-sensitive adhesive composition of the present invention has a good balance between adhesive strength and heat-and-moisture resistance, so an electronic component fixing sheet (tape) or an electronic component label sheet (tape) ) And an adhesive for bonding in an optical display or touch sensor.
  • an adhesive for bonding in an optical display or touch sensor for example, bonding of an optical display panel and a touch panel, bonding of an optical display panel and a protection panel, bonding of a touch panel and a protection panel, bonding of an optical display panel and an optical display panel, optical display panel and parallax barrier Can be used as a pressure-sensitive adhesive.
  • the adhesive layer obtained from the adhesive of this invention is excellent also in a softness

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention concerne une composition adhésive sensible à la pression durcissable par rayonnement d'énergie active comprenant : un composé (méth)acrylate d'uréthane (A) qui est obtenu par la réaction d'un composé isocyanate polyvalent (a1), d'un composé (méth)acrylate contenant des groupes hydroxyle (a2) et d'un composé polyol (a3), et a un poids moléculaire moyen en poids de 20 000 à 120 000 ; et des monomères à insaturation éthylénique (B) [à condition que le composé (méth)acrylate d'uréthane (A) soit exclu], caractérisée en ce que les monomères à insaturation éthylénique (B) comprennent un monomère contenant un hétérocycle (b1) et un monomère contenant un groupe hydroxyle (b2) et le rapport (en poids) de la teneur en monomère contenant un hétérocycle (b1) à la teneur en monomère contenant un groupe hydroxyle (b2) [(b1):(b2)] est de 25:75 à 80:20.
PCT/JP2015/070536 2014-07-22 2015-07-17 Composition adhésive sensible à la pression durcissable par rayonnement d'énergie active, adhésif sensible à la pression et feuille adhésive sensible à la pression l'utilisant Ceased WO2016013510A1 (fr)

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JP2015535913A JP6610256B2 (ja) 2014-07-22 2015-07-17 活性エネルギー線硬化性粘着剤組成物、これを用いてなる粘着剤、及び粘着シート
CN201580039727.3A CN106536653B (zh) 2014-07-22 2015-07-17 活性能量射线固化性粘合剂组合物、使用其而得到的粘合剂和粘合片

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CN115943077A (zh) * 2019-12-31 2023-04-07 阿科玛法国公司 包含具有1,3-二氧杂环戊烷环的单(甲基)丙烯酸酯的交联性组合物
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WO2019069621A1 (fr) * 2017-10-05 2019-04-11 株式会社有沢製作所 Composition de résine photodurcissable et feuille adhésive
CN111149192A (zh) * 2017-12-07 2020-05-12 琳得科株式会社 工件加工用片及已加工工件的制造方法
CN111149192B (zh) * 2017-12-07 2023-09-15 琳得科株式会社 工件加工用片及已加工工件的制造方法
EP3715432A1 (fr) * 2019-03-27 2020-09-30 3M Innovative Properties Company Composition adhésive sensible à la pression présentant des caractéristiques de transparence
CN115943077A (zh) * 2019-12-31 2023-04-07 阿科玛法国公司 包含具有1,3-二氧杂环戊烷环的单(甲基)丙烯酸酯的交联性组合物
JP2025086429A (ja) * 2023-11-28 2025-06-09 ａｒｔｉｅｎｃｅ株式会社 活性エネルギー線硬化性組成物、およびそれを用いた積層体
JP7694637B2 (ja) 2023-11-28 2025-06-18 ａｒｔｉｅｎｃｅ株式会社 活性エネルギー線硬化性組成物、およびそれを用いた積層体

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