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WO2025205577A1 - Composition de résine photopodurcissable - Google Patents

Composition de résine photopodurcissable

Info

Publication number
WO2025205577A1
WO2025205577A1 PCT/JP2025/011399 JP2025011399W WO2025205577A1 WO 2025205577 A1 WO2025205577 A1 WO 2025205577A1 JP 2025011399 W JP2025011399 W JP 2025011399W WO 2025205577 A1 WO2025205577 A1 WO 2025205577A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
resin composition
photocurable resin
acrylate
acrylic monomer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/011399
Other languages
English (en)
Japanese (ja)
Inventor
和裕 川端
祐希 河田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Fuller Co Ltd
Original Assignee
Sekisui Fuller Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sekisui Fuller Co Ltd filed Critical Sekisui Fuller Co Ltd
Publication of WO2025205577A1 publication Critical patent/WO2025205577A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Definitions

  • the present invention relates to a photocurable resin composition.
  • Photocurable resin compositions have traditionally been used as adhesives for glass and synthetic resins. Photocurable resin compositions are cured by exposure to light, thereby exhibiting adhesive properties. Photocurable resin compositions generate shrinkage stress during photocuring.
  • Patent Document 1 discloses a photocurable adhesive composition containing (a) an oligomer having a photocurable functional group, (b) a long-chain hydrocarbon-based (meth)acrylate monomer, and (c) a cyclic (meth)acrylate monomer.
  • the present invention provides a photocurable resin composition that exhibits low shrinkage stress during curing and imparts minimal stress to the adherend upon curing. It also provides a photocurable resin composition that has excellent adhesion, is resistant to fogging due to humidity, and can produce a cured product with reduced yellowing due to high-temperature environments.
  • the photocurable resin composition of the present invention has low shrinkage stress during curing, and therefore exerts little stress on the adherend during curing.
  • the photocurable resin composition of the present invention can produce a cured product with excellent adhesive properties.
  • the photocurable resin composition of the present invention reduces moisture absorption, making it less susceptible to clouding due to moisture, and can produce cured products with reduced yellowing due to high-temperature environments.
  • the upper or lower limit of a numerical range in one stage can be arbitrarily combined with the upper or lower limit of a numerical range in another stage.
  • the upper or lower limit of that numerical range may be replaced with a value shown in an example or a value that can be unambiguously derived from an example.
  • numbers connected with " ⁇ " mean a numerical range that includes the numbers before and after " ⁇ " as the upper and lower limits.
  • the photocurable resin composition of the present invention contains a water-insoluble (meth)acrylic monomer (A) having a glass transition temperature Tg of 50°C or higher, and a polyfunctional (meth)acrylic oligomer (B) having a polydiene skeleton with a hydrogenation rate of 90% or higher.
  • (meth)acrylic refers to having an acryloyl group [formula (1)] or a methacryloyl group [formula (2)] in the molecule.
  • *1 represents a bond and represents a single bond.
  • the photocurable resin composition contains a (meth)acrylic monomer (A) (hereinafter sometimes simply referred to as "(meth)acrylic monomer (A)”) that has a glass transition temperature Tg of 50°C or higher and is water-insoluble.
  • the photocurable resin composition contains a (meth)acrylic monomer (A).
  • A a (meth)acrylic monomer
  • B polyfunctional (meth)acrylic oligomer
  • the photocurable resin composition produces a cured product with excellent adhesive properties. Furthermore, the cured product of the photocurable resin composition exhibits reduced cloudiness due to moisture and reduced yellowing due to high-temperature environments.
  • the glass transition temperature Tg of the (meth)acrylic monomer (A) is 50°C or higher, preferably 90°C or higher, more preferably 120°C or higher, more preferably 150°C or higher, more preferably 160°C or higher, and more preferably 170°C or higher.
  • the glass transition temperature Tg of the (meth)acrylic monomer (A) is preferably 250°C or lower, more preferably 230°C or lower, more preferably 210°C or lower, more preferably 200°C or lower, and more preferably 190°C or lower.
  • the cured product of the photocurable resin composition exhibits reduced cloudiness due to humidity and reduced yellowing due to high-temperature environments.
  • the glass transition temperature Tg of the (meth)acrylic monomer (A) is 250°C or lower, the stress applied to the adherend during curing of the photocurable resin composition is reduced, which is preferable.
  • the glass transition temperature Tg of (meth)acrylic monomer (A) refers to the temperature measured in accordance with JIS K7121:1987.
  • the (meth)acrylic monomer (A) is water-insoluble. Because the (meth)acrylic (A) is water-insoluble, the photocurable resin composition produces a cured product with excellent adhesive properties, and further, the cured product of the photocurable resin composition exhibits reduced cloudiness due to moisture.
  • the (meth)acrylic monomer (A) may be any monomer that has a glass transition temperature Tg of 50°C or higher and is water-insoluble, and examples thereof include (meth)acrylate monomers having a monocyclo ring, (meth)acrylate monomers having a bicyclo ring, and (meth)acrylate monomers having a tricyclo ring.
  • the (meth)acrylic monomers (A) may be used alone or in combination of two or more.
  • (meth)acrylate refers to acrylate or methacrylate.
  • the cyclic skeleton such as a monocyclo ring, bicyclo ring, or tricyclo ring is preferably a saturated alicyclic skeleton.
  • the photocurable resin composition produces a cured product with superior adhesive properties, and further, the cured product of the photocurable resin composition exhibits reduced cloudiness due to moisture and reduced yellowing due to high-temperature atmospheres.
  • An alicyclic structure is a structure in which carbon atoms are bonded in a ring and does not have aromaticity.
  • Examples of (meth)acrylates having a monocyclo ring include cyclohexyl (meth)acrylate, morpholine (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and 4-tert-butylcyclohexyl (meth)acrylate, with 4-tert-butylcyclohexyl (meth)acrylate being preferred.
  • Examples of (meth)acrylate monomers having a bicyclo ring include dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and isobornyl (meth)acrylate.
  • isobornyl (meth)acrylate and dicyclopentanyl (meth)acrylate are more preferred, with isobornyl methacrylate and dicyclopentanyl methacrylate being even more preferred. This is because the photocurable resin composition produces a cured product with superior adhesive properties, and furthermore, the cured product of the photocurable resin composition exhibits reduced cloudiness due to moisture and reduced yellowing due to high-temperature environments.
  • Examples of (meth)acrylate monomers having a tricyclo ring include (meth)acrylate compounds having an adamantane skeleton.
  • the (meth)acrylic monomer (A) may be polyfunctional.
  • the photocurable resin composition has a small shrinkage stress during curing, and the stress applied to the adherend is small.
  • Examples of the polyfunctional (meth)acrylic monomer (A) include tricyclodecane dimethanol di(meth)acrylate and ethoxylated bisphenol A di(meth)acrylate.
  • the polyfunctional (meth)acrylic monomer (A) preferably has two or more (meth)acryloyl groups in the molecule.
  • the (meth)acryloyl group refers to an acryloyl group (CH 2 ⁇ CHCO—) or a methacryloyl group (CH 2 ⁇ C(CH 3 )CO—).
  • the photocurable resin composition contains a polyfunctional (meth)acrylic oligomer (B) having a polydiene skeleton with a hydrogenation rate of 90% or more (hereinafter, may be simply referred to as "polyfunctional (meth)acrylic oligomer (B)").
  • the photocurable resin composition contains the polyfunctional (meth)acrylic oligomer (B), the photocurable resin composition has low shrinkage stress during curing and imparts little stress to the adherend. Furthermore, the photocurable resin composition produces a cured product with excellent adhesive properties, and the cured product of the photocurable resin composition exhibits reduced cloudiness due to moisture and reduced yellowing due to high-temperature environments.
  • the hydrogenation rate of the polyfunctional (meth)acrylic oligomer (B) is 90% or more, preferably 91% or more, more preferably 92% or more, more preferably 93% or more, and even more preferably 94% or more.
  • the hydrogenation rate of the polyfunctional (meth)acrylic oligomer (B) is the proportion of hydrogen added to unsaturated bonds contained in the molecule, and when all unsaturated bonds are hydrogenated, the hydrogenation rate is 100%.
  • the polyfunctional (meth)acrylic oligomer (B) is polyfunctional, which reduces the shrinkage stress of the photocurable resin composition during curing and reduces the stress applied to the adherend. It is preferable that the polyfunctional (meth)acrylic oligomer (B) has two or more (meth)acryloyl groups in its molecule.
  • the polyfunctional (meth)acrylic oligomer (B) having a hydrogenated polydiene skeleton does not have a conjugated diene structure (a conjugated diene structure in which a double bond is separated by one single bond).
  • urethane (meth)acrylates examples include hydrogenated 1,2-polybutadiene terminal urethane (meth)acrylate (for example, "TEAI-1000” manufactured by Nippon Soda Co., Ltd.).
  • urethane (meth)acrylate refers to a urethane (meth)acrylate having a urethane bond within the molecule, obtained by reacting (for example, by polycondensation) a polyol compound, an organic polyisocyanate compound, and a hydroxy (meth)acrylate.
  • polyol compounds include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, 1,4-butanediol, polybutylene glycol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 2,2-butylethyl-1,3-propanediol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, polycaprolactone, trimethylolethane, trimethylolpropane, polytrimethylolpropane, pentaerythritol, polypentaeryth
  • hydrogenated conjugated diene polyols are preferred because they have a hydrogenated conjugated diene skeleton.
  • hydrogenated conjugated diene polyols hydrogenated polybutadiene polyols and hydrogenated polyisoprene polyols are more preferred, with hydrogenated polybutadiene polyols (hydrogenated polybutadiene polyols) being more preferred.
  • hydrogenated polybutadiene polyols hydrogenated 1,2-polybutadiene polyols are preferred.
  • Organic polyisocyanate compounds are not particularly limited, and examples include aromatic, aliphatic, cyclic aliphatic, and alicyclic polyisocyanates.
  • organic polyisocyanate compounds include tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), hydrogenated diphenylmethane diisocyanate (H-MDI), polyphenylmethane polyisocyanate (crude MDI), modified diphenylmethane diisocyanate (modified MDI), hydrogenated xylylene diisocyanate (H-XDI), xylylene diisocyanate (XDI), and hexamethylene diisocyanate (HM Suitable polyisocyanates include tolylene diisocyanate (TDI), trimethylhexamethylene diisocyanate (TMXDI), tetramethylxylylene diisocyanate (m-TMXDI), isophorone diisocyanate (IPD
  • tolylene diisocyanate (TDI), hydrogenated xylylene diisocyanate (H-XDI), and isophorone diisocyanate (IPDI) are preferred, with tolylene diisocyanate (TDI) and isophorone diisocyanate (IPDI) being more preferred, and isophorone diisocyanate (IPDI) being even more preferred.
  • the average molecular weight of the polyfunctional (meth)acrylic oligomer (B) is preferably 6,000 or more, more preferably 10,000 or more, more preferably 15,000 or more, and more preferably 20,000 or more.
  • the average molecular weight of the polyfunctional (meth)acrylic oligomer (B) is preferably 50,000 or less, more preferably 40,000 or less, and more preferably 30,000 or less.
  • the average molecular weight of the polyfunctional (meth)acrylic oligomer (B) is a value measured as follows.
  • the average molecular weight of the polyfunctional (meth)acrylic oligomer (B) is measured by gel permeation chromatography (GPC) under the following conditions using tetrahydrofuran as the solvent, with a calibration curve prepared using commercially available standard polystyrene. For example, it can be measured using the following measuring device and under the following measuring conditions.
  • Measurement equipment ACQUITY APC system manufactured by Waters Measurement conditions: Column: HSPgelTM HR MB-M manufactured by Waters Mobile phase: tetrahydrofuran 0.5 mL/min Detector: RI detector Standard material: polystyrene SEC temperature: 40°C
  • the content of the polyfunctional (meth)acrylic oligomer (B) in the photocurable resin composition is preferably 40 parts by mass or more, more preferably 45 parts by mass or more, and more preferably 50 parts by mass or more, per 100 parts by mass of the (meth)acrylic monomer (A).
  • the content of the polyfunctional (meth)acrylic oligomer (B) in the photocurable resin composition is preferably 150 parts by mass or less, more preferably 130 parts by mass or less, more preferably 110 parts by mass or less, and more preferably 90 parts by mass or less, per 100 parts by mass of the (meth)acrylic monomer (A).
  • the content of the polyfunctional (meth)acrylic oligomer (B) is 40 parts by mass or more, the shrinkage stress during curing of the photocurable resin composition is reduced, the stress applied to the adherend is reduced, and the cloudiness due to moisture of the cured product of the photocurable resin composition and yellowing in a high-temperature atmosphere are reduced.
  • the content of the polyfunctional (meth)acrylic oligomer (B) is 150 parts by mass or less, the adhesiveness of the cured product of the photocurable resin composition is improved.
  • the photocurable resin composition preferably contains a (meth)acrylic monomer (C) (hereinafter, sometimes simply referred to as "(meth)acrylic monomer (C)”) having a glass transition temperature Tg of 0° C. or lower.
  • the glass transition temperature Tg of the (meth)acrylic monomer (C) is measured in the same manner as that of the (meth)acrylic monomer (A).
  • the glass transition temperature Tg of the (meth)acrylic monomer (C) is preferably 0°C or lower, more preferably -10°C or lower, more preferably -20°C or lower, more preferably -30°C or lower, more preferably -40°C or lower, more preferably -50°C or lower, and more preferably -60°C or lower.
  • the glass transition temperature Tg of the (meth)acrylic monomer (C) is preferably -80°C or higher, more preferably -70°C or higher.
  • (Meth)acrylic monomers (C) having a glass transition temperature Tg of 0°C or lower are not particularly limited, and examples include normal octyl (meth)acrylate, isooctyl (meth)acrylate, dodecyl (meth)acrylate, isodecyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isostearyl (meth)acrylate, butyl (meth)acrylate, ethoxy-diethylene glycol (meth)acrylate, phenoxyethyl (meth)acrylate, and phenoxy-polyethylene glycol (meth)acrylate.
  • the content of (meth)acrylic monomer (C) in the photocurable resin composition is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, more preferably 8 parts by mass or more, more preferably 10 parts by mass or more, and more preferably 12 parts by mass or more, per 100 parts by mass of (meth)acrylic monomer (A).
  • the content of (meth)acrylic monomer (C) in the photocurable resin composition is preferably 35 parts by mass or less, more preferably 30 parts by mass or less, and more preferably 25 parts by mass or less, per 100 parts by mass of (meth)acrylic monomer (A).
  • the photocurable resin composition may contain a photopolymerization initiator.
  • the photocurable resin composition may contain a photopolymerization initiator, the photocurable resin composition can be easily photopolymerized and cured.
  • the photopolymerization initiator is not particularly limited, and examples thereof include ⁇ -hydroxyketone-based photopolymerization initiators, acylphosphine oxide-based photopolymerization initiators, thioxanthone-based photopolymerization initiators, and triazine-based photopolymerization initiators. These initiators have excellent compatibility with the (meth)acrylic monomer (A) and polyfunctional (meth)acrylic oligomer (B), excellent curing properties of the photocurable resin composition, and can reduce shrinkage stress during curing of the photocurable resin composition, thereby reducing stress on the adherend.
  • ⁇ -hydroxyketone-based photopolymerization initiators and acylphosphine oxide-based photopolymerization initiators are preferred, with ⁇ -hydroxyketone-based photopolymerization initiators being more preferred.
  • Photopolymerization initiators may be used alone or in combination of two or more types.
  • ⁇ -Hydroxyketone photopolymerization initiators are not particularly limited, and examples include 1-hydroxycyclohexyl phenyl ketone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- ⁇ 4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl ⁇ -2-methyl-propan-1-one, and 2-hydroxy-2-methyl-1-phenyl-propan-1-one.
  • acylphosphine oxide photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide.
  • thioxanthone-based photopolymerization initiator is 2,4-diethylthioxanthone.
  • triazine-based photopolymerization initiators examples include 2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(5-methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[(4-methoxyphenyl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, and 2-[(3,4-dimethoxyphenyl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine.
  • the content of the photopolymerization initiator in the photocurable resin composition is preferably 0.5 parts by mass or more, and more preferably 0.7 parts by mass or more, per 100 parts by mass of the (meth)acrylic monomer (A).
  • the content of the photopolymerization initiator in the photocurable resin composition is preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 2 parts by mass or less, per 100 parts by mass of the (meth)acrylic monomer (A).
  • the content of the photopolymerization initiator is within the above range, the shrinkage stress during curing of the photocurable resin composition can be further reduced, thereby reducing the stress applied to the adherend.
  • the photocurable resin composition may contain a silane coupling agent, a thixotropic agent, an adhesion-imparting resin, a plasticizer, non-thermally expandable fine particles, a dye, a pigment, a flame retardant, a surfactant, and the like, within the range that does not impair the physical properties of the composition.
  • the photocurable resin composition preferably contains a silane coupling agent.
  • the silane coupling agent is not particularly limited, and examples include vinyltrimethoxysilane, vinyltriethoxysilane, (3-acryloxypropyl)trimethoxysilane, (3-methacryloxypropyl)trimethoxysilane, (3-methacryloxypropyl)triethoxysilane, (3-methacryloxyoctyl)trimethoxysilane, and (3-mercaptopropyl)trimethoxysilane.
  • Alkoxysilanes are preferred, trialkoxysilanes are more preferred, trimethoxysilane and triethoxysilane are more preferred, and vinyltriethoxysilane, (3-acryloxypropyl)trimethoxysilane, and (3-methacryloxypropyl)trimethoxysilane are preferred.
  • the content of the silane coupling agent in the photocurable resin composition is preferably 1 part by mass or more, more preferably 1.5 parts by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the (meth)acrylic monomer (A).
  • the content of the silane coupling agent in the photocurable resin composition is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and even more preferably 6 parts by mass or less, per 100 parts by mass of the (meth)acrylic monomer (A).
  • the method for producing the photocurable resin composition is not particularly limited, and the photocurable resin composition can be produced, for example, by uniformly mixing the (meth)acrylic monomer (A), the polyfunctional (meth)acrylic oligomer (B), and compounds contained as necessary in a general manner, preferably under reduced pressure.
  • the photocurable resin composition contains both the (meth)acrylic monomer (A) and the polyfunctional (meth)acrylic oligomer (B), it is possible to achieve the above-mentioned conflicting goals, namely, reducing the stress applied to the adherend when the photocurable resin composition is cured, while improving the adhesion of the cured product of the photocurable resin composition and reducing cloudiness due to moisture. Furthermore, it is also characterized by being able to reduce the yellowing of the cured product of the photocurable resin composition caused by a high-temperature atmosphere.
  • the tensile modulus of elasticity of the cured product of the photocurable resin composition is preferably 50 MPa or more, more preferably 100 MPa or more, more preferably 150 MPa or more, and more preferably 200 MPa or more.
  • the tensile modulus of elasticity of the cured product of the photocurable resin composition is preferably 900 MPa or less, more preferably 800 MPa or less, more preferably 700 MPa or less, and more preferably 600 MPa or less.
  • the adhesiveness of the cured product of the photocurable resin composition can be improved, clouding due to moisture in the cured product of the photocurable resin composition can be further reduced, and yellowing due to high-temperature atmospheres can be further reduced.
  • the tensile modulus of elasticity of the cured product of the photocurable resin composition is 900 MPa or less, shrinkage stress during curing of the photocurable resin composition can be further reduced.
  • the tensile modulus of elasticity of the cured photocurable resin composition is the value measured in accordance with JIS K7161-1 under conditions of a dumbbell thickness of 1.0 mm and a tensile speed of 10 mm/min.
  • the maximum stress of the cured product of the photocurable resin composition is preferably 5 MPa or more, more preferably 6 MPa or more, and even more preferably 7 MPa or more.
  • the maximum stress of the cured product of the photocurable resin composition is preferably 20 MPa or less, more preferably 16 MPa or less, and even more preferably 15 MPa or less.
  • a maximum stress of 5 MPa or more in the cured product of the photocurable resin composition can improve the adhesion of the cured product of the photocurable resin composition, further reduce clouding due to moisture in the cured product of the photocurable resin composition, and further reduce yellowing due to high-temperature environments.
  • a maximum stress of 20 MPa or less in the cured product of the photocurable resin composition can further reduce shrinkage stress during curing of the photocurable resin composition, thereby reducing stress on the adherend.
  • the maximum stress of the cured product of the photocurable resin composition is the value measured in accordance with JIS K7161-1 under conditions of a dumbbell thickness of 1.0 mm and a tensile speed of 10 mm/min.
  • the curing shrinkage stress is preferably 0.06 MPa or less, more preferably 0.05 MPa or less. If the curing shrinkage stress is 0.06 MPa or less, the shrinkage stress during curing of the photocurable resin composition is small, reducing the stress applied to the adherend and reducing the occurrence of optical distortion in the adherend.
  • the curing shrinkage stress of the photocurable resin composition is a value measured at room temperature of 23°C in accordance with JIS K6941. For example, it can be measured by curing under the following conditions using an apparatus commercially available from Acroedge Co., Ltd. under the trade name "Custron". Light source: Panasonic LED-Aicure (wavelength: 365 nm) Irradiation intensity: 65mW/cm 2 Irradiation time: 300 seconds
  • a laminate is produced by placing the adherends in a state where the photocurable resin composition is interposed between the opposing surfaces of the adherends (lamination process).
  • a laminate may also be produced by laminating three or more adherends together with the photocurable resin composition interposed between the opposing surfaces of the adherends.
  • the photocurable resin composition is a one-component type, the complicated process of mixing two components is not required to create a laminate, making it easy to manufacture the laminate.
  • the entire resulting laminate is irradiated with radiation in the stacking direction of the laminate, curing the photocurable resin composition sandwiched between the opposing surfaces of the adherends that make up the laminate and producing a cured product (polymer) (curing process).
  • This cured product can bond the adherends together.
  • the cured product produced by curing the photocurable resin composition has excellent adhesive properties, making it possible to firmly bond two adherends together via the cured product.
  • the peak wavelength of the radiation is preferably 500 nm or less, as this provides excellent curing properties for the photocurable resin composition.
  • the radiation is preferably light with a peak wavelength of 320 nm or more. By using radiation with a peak wavelength of 320 nm or more, the photocurable resin composition can be cured deeply to produce a cured product.
  • the cured product of the photocurable resin composition that bonds and integrates the adherends has low water absorption, reducing the occurrence of clouding due to humidity and reducing yellowing caused by high-temperature environments.
  • a dumbbell-shaped test piece (Type 3 specified in JIS K6251) measuring 50 mm in length, 25 mm in width, and 1.0 mm in thickness was prepared.
  • the test piece was irradiated with ultraviolet light having a peak wavelength of 365 nm at an irradiation intensity of 65 mW/cm for 2 minutes to cure the photocurable resin composition and thus the test piece.
  • the tensile modulus of the cured test specimens was measured in accordance with JIS K7161-1 under conditions of a dumbbell thickness of 1.0 mm and a tensile speed of 10 mm/min.
  • a dumbbell-shaped test piece (Type 3 specified in JIS K6251) measuring 50 mm in length, 25 mm in width, and 1.0 mm in thickness was prepared.
  • the test piece was irradiated with ultraviolet light having a peak wavelength of 365 nm at an irradiation intensity of 65 mW/cm for 2 minutes to cure the photocurable resin composition and thus the test piece.
  • a cylindrical water bath with a square base measuring 22.5 cm on each side and a height of 17 cm was prepared, and water was poured into the water bath to a depth of 4 cm.
  • a 200-mesh stainless steel wire mesh was placed horizontally in the water bath, 11 cm vertically above the water surface, and a steam-permeable cloth was placed on top of the wire mesh. The cured test specimen was placed on top of the cloth.
  • the photocurable resin composition thus obtained was used to prepare a plate-shaped test piece measuring 50 mm in length, 25 mm in width, and 1.0 mm in thickness.
  • the test piece was irradiated with ultraviolet light having a peak wavelength of 365 nm at an irradiation intensity of 65 mW/ cm for 2 minutes to cure the photocurable resin composition and the test piece.
  • the test piece was placed in an oven at 135°C and heated for 100 hours.
  • the test piece was removed from the oven and left in an atmosphere at 25°C for 24 hours.
  • the post-heating transmittance T1 of the test piece after heating was measured using an ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation, trade name "UV-3600 Plus").

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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)

Abstract

La présente invention concerne une composition de résine photodurcissable qui présente moins de contrainte de retrait pendant le durcissement, qui applique moins de contrainte sur une surface adhésive pendant le durcissement, et qui peut produire un produit durci qui présente une adhésivité supérieure, et dans laquelle la formation de buée due à l'humidité est réduite et le jaunissement se produisant dans une atmosphère à haute température est réduit. Une composition de résine photodurcissable selon la présente invention est caractérisée en ce qu'elle comprend un monomère (méth)acrylique (A) qui est insoluble dans l'eau et qui présente une température de transition vitreuse Tg supérieure ou égale à 50 °C ; et un oligomère (méth)acrylique polyfonctionnel (B) qui comporte un squelette à base de polydiène présentant un taux d'hydrogénation supérieur ou égal à 90 %.
PCT/JP2025/011399 2024-03-29 2025-03-24 Composition de résine photopodurcissable Pending WO2025205577A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2024-057837 2024-03-29
JP2024057837 2024-03-29

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WO2025205577A1 true WO2025205577A1 (fr) 2025-10-02

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013031678A1 (fr) * 2011-08-26 2013-03-07 電気化学工業株式会社 Composition de résine durcissable
WO2013187508A1 (fr) * 2012-06-15 2013-12-19 昭和電工株式会社 Composition polymérisable, polymère, feuille adhésive optique, dispositif d'affichage d'image, et procédé de fabrication de dispositif d'affichage d'image
JP2020045416A (ja) * 2018-09-19 2020-03-26 アイカ工業株式会社 光硬化性粘着樹脂組成物
JP2023030451A (ja) * 2021-08-23 2023-03-08 積水フーラー株式会社 粘着部材及びその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013031678A1 (fr) * 2011-08-26 2013-03-07 電気化学工業株式会社 Composition de résine durcissable
WO2013187508A1 (fr) * 2012-06-15 2013-12-19 昭和電工株式会社 Composition polymérisable, polymère, feuille adhésive optique, dispositif d'affichage d'image, et procédé de fabrication de dispositif d'affichage d'image
JP2020045416A (ja) * 2018-09-19 2020-03-26 アイカ工業株式会社 光硬化性粘着樹脂組成物
JP2023030451A (ja) * 2021-08-23 2023-03-08 積水フーラー株式会社 粘着部材及びその製造方法

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