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
  • C08F290/06—Polymers provided for in subclass C08G
• • 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
  • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• • 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
  • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
• • 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
  • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
  • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
  • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
• • 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

Definitions

• the present invention relates to a curable resin composition.
• Patent Document 1 proposes a photocurable inkjet ink containing a monofunctional polymerizable monomer having hydroxyl, a bifunctional (meth) acrylate, and a photopolymerization initiator.
• an adhesive for attaching display elements and members such as a front lens and a panel, a cover lens including a color filter, a TFT (thin film diode), etc. 2 includes a urethane (meth) acrylate oligomer having two or more (meth) acryloyl groups in one molecule, a (meth) acrylate having a hydroxyl group, a non-radically polymerizable flexible component, and a radical photopolymerization initiator. And an ultraviolet curable adhesive composition characterized by containing the above.
• the present invention provides a light and thermosetting resin composition that solves the above problems and is excellent in adhesion between substrates even when an inorganic substrate and an organic substrate are bonded together. With the goal.
• the inventor contains a (meth) acrylic oligomer (component A) having a molecular weight of 5,000 or more, a (meth) acrylic monomer (component B), and a light and / or thermal radical polymerization initiator (component C).
• component A a (meth) acrylic oligomer having a molecular weight of 5,000 or more
• component B a (meth) acrylic monomer
• component C a light and / or thermal radical polymerization initiator
• the present invention has the following configuration.
• component B contains a (meth) acrylic monomer of 10 mPa ⁇ s or less.
• a light and thermosetting resin composition that is excellent in adhesion between substrates even when an inorganic substrate and an organic substrate are bonded together.
• (Meth) acrylate has at least one of acrylate and methacrylate.
• the “(meth) acryloyl group” has at least one of an acryloyl group and a methacryloyl group.
• “(Meth) acryl” has at least one of acrylic and methacrylic meanings.
• the curable resin composition (hereinafter also simply referred to as “composition”) includes a (meth) acrylic oligomer (component A), a (meth) acrylic monomer (component B) having a molecular weight of 5,000 or more, and radical photopolymerization. It contains at least one radical polymerization initiator (component C) selected from the group consisting of an initiator and a thermal radical polymerization initiator, and has a viscosity of 150 mPa ⁇ s or less.
• the (meth) acryl oligomer (component A) having a molecular weight of 5,000 or more has one or more (meth) acryloyl groups in the molecule.
• the molecular weight of the (meth) acrylate oligomer is preferably from 5,000 to 100,000, more preferably from 10,000 to 70,000, and particularly preferably from 20,000 to 50,000.
• the molecular weight is a weight average molecular weight measured by gel permeation chromatography (GPC) and converted using a standard polystyrene calibration curve.
• the (meth) acrylate oligomer is not particularly limited, and is selected from the group consisting of a (meth) acrylate oligomer having a polyurethane skeleton, a (meth) acrylate oligomer having a polyisoprene skeleton, and a (meth) acrylate oligomer having a polybutadiene skeleton. 1 type or more to be mentioned. These (meth) acrylate oligomers can be used alone or in combination of two or more.
• the (meth) acrylate oligomer having a polyurethane skeleton is an aliphatic type (however, excluding the rubber type and hydrogenated rubber type described later), one or more selected from the group consisting of polybutadiene and polyisoprene, and the like.
• One or more selected from the group consisting of hydrogenated polybutadiene and hydrogenated polyisoprene, and the like include hydrogenated rubber-based, polyether-based, polycarbonate-based, polyester-based, or a combination thereof. .
• Urethane (meth) acrylate can be produced, for example, by reacting an organic diisocyanate with a hydroxyl group-containing (meth) acrylate compound by a method as described in JP-A-2008-260898.
• Organic diisocyanate is not particularly limited as long as it is a compound having two or more isocyanato groups, and is an aromatic, aliphatic, or alicyclic polyisocyanate such as tolylene diisocyanate, diphenylmethane diisocyanate, hydrogenated.
• the hydroxyl group-containing (meth) acrylate compound is not particularly limited as long as it is a (meth) acrylate compound having one or more hydroxyl groups in the molecule.
• Specific examples of such a hydroxyl group-containing (meth) acrylate compound include, in addition to those described later in Component B, for example, a phosphorus atom such as 2-hydroxyethyl (meth) acryloyl phosphate, and one or more in the molecule.
• a (meth) acrylate compound having two or more hydroxyl groups and (meth) having two or more hydroxyl groups in a molecule such as glycerin di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, etc.
• An acrylate compound is mentioned.
• the (meth) acrylate oligomer having a polyisoprene skeleton and the (meth) acrylate oligomer having a polybutadiene skeleton may be a hydrogenated product.
• Commercially available products can be used as the (meth) acrylate oligomer having a polybutadiene backbone and the (meth) acrylate oligomer having a polyisoprene backbone.
• UC-1 manufactured by Kuraray Co., Ltd .: molecular weight 25,000
• UC-203 manufactured by Kuraray Co., Ltd .: molecular weight 35,000
• the (meth) acrylate oligomer having a polyisoprene skeleton and the (meth) acrylate oligomer having a polybutadiene skeleton do not have a urethane bond.
• the (meth) acrylate oligomer is preferably a (meth) acrylate oligomer having a polyurethane skeleton, a polyether urethane (meth) acrylate oligomer, a polyester urethane (meth) acrylate oligomer, an aliphatic urethane (meth) acrylate oligomer, or rubber.
• One or more selected from the group consisting of a urethane urethane (meth) acrylate oligomer and a hydrogenated rubber urethane (meth) acrylate oligomer is more preferred.
• the (meth) acrylate oligomer may be used alone or in combination of two or more.
• the (meth) acrylic monomer (component B) is not particularly limited as long as it is a monomer resin having one or more (meth) acryloyl groups in the molecule, but one type selected from the group consisting of monofunctional (meth) acrylate monomers. The above is preferable.
• the viscosity of Component B is not particularly limited, but is preferably 10 mPa ⁇ s or less, and more preferably 8 mPa ⁇ s or less. If it is the viscosity of such a component B, there exists a tendency for the viscosity of a composition to be reduced efficiently.
• the monofunctional (meth) acrylate monomer is not particularly limited as long as it is a (meth) acrylate compound having one (meth) acryloyl group in the molecule, and alicyclic (meth) acrylate and hydroxyl group-containing (meth) acrylate. , One or more selected from the group consisting of alkyl (meth) acrylates and aromatic (meth) acrylates.
• the alkyl (meth) acrylate is not particularly limited, and n-butyl (meth) acrylate, i-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, Examples include isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and isostearyl (meth) acrylate.
• the alkyl (meth) acrylate is preferably a C 6 -C 30 alkyl (meth) acrylic monomer.
• Alkyl (meth) acrylate flexibility imparted to the cured product is lowered the viscosity of the composition more effectively, in terms of reducing the odor of the composition, the alkyl (meth) acrylates of C 6 ⁇ C 30 preferable.
• the C 6 -C 30 alkyl is linear or branched, and is preferably branched from the viewpoint of better adhesion.
• C 6 -C 30 alkyl preferably has 6 to 20 carbon atoms, more preferably 8 to 16 carbon atoms.
• Hydroxyl group-containing (meth) acrylates include hydroxy-substituted alkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
• Examples of the alicyclic (meth) acrylate include dicyclopentenyloxyethyl (meth) acrylate, norbornene (meth) acrylate, dicyclopentanyl (meth) acrylate, and isobornyl (meth) acrylate.
• Component B contains alicyclic (meth) acrylate, hydroxyl group-containing (meth) acrylate, and C 6 -C 30 alkyl (meth) acrylate from the viewpoint of better adhesion to both inorganic and organic substrates. More preferably.
• the composition contains at least one radical polymerization initiator selected from the group consisting of a photo radical polymerization initiator and a thermal radical polymerization initiator in order to accelerate curing.
• the radical polymerization initiator may be used alone or in combination of two or more.
• the composition contains a radical photopolymerization initiator, the composition is a photocurable resin composition that cures with energy rays.
• the composition contains a thermal radical polymerization initiator, the composition is a thermosetting resin composition that cures with heat.
• the composition is a light and / or thermosetting resin composition that is cured by energy rays and / or heat by including a photo radical polymerization initiator and a heat radical polymerization initiator.
• the radical photopolymerization initiator is not particularly limited as long as it is a compound that generates radicals upon irradiation with light.
• Photoradical polymerization initiators include benzophenone, diacetyl, benzyl, benzoin, ⁇ -bromoacetophenone, chloroacetone, acetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetone, p-dimethylaminoacetophenone, p-dimethylaminopropiophenone, 2-chlorobenzophenone, p, p'-bisdiethylaminobenzophenone, Michler's ketone, benzoin methyl ether, benzoin isobutyl ether, benzoin-n-butyl ether, benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2 -Hydroxy-2-
• the radical photopolymerization initiator is preferably a carbonyl group-based photopolymerization initiator, particularly preferably 1-hydroxy-cyclohexyl-phenyl-ketone, from the viewpoint of increasing the speed of curing and reducing coloring after photocuring.
• the radical photopolymerization initiator may be used alone or in combination of two or more.
• the thermal radical polymerization initiator is not particularly limited as long as it is a compound that generates radicals upon heating, and examples thereof include organic peroxides and azo compounds, and organic peroxides are preferred.
• the organic peroxide may be an organic compound containing a peroxy group (—O—O—).
• a peroxy group —O—O—
• organic peroxides include diacyl peroxides such as dilauroyl peroxide, dibenzoyl peroxide, bis-3,5,5-trimethylhexanoyl peroxide; 1,1,3,3-tetramethylbutyl hydro Peroxides, cumene hydroperoxide (eg Kayakumen H from Kayaku Aguso), hydroperoxides such as t-butyl hydroperoxide; t-hexylperoxy 2-ethylhexanoate, dicumyl peroxide, 2,5-dimethyl -2,5-di (t-butylperoxy) hexane, 1,3-bis (t-butylperoxyisopropyl) benzene, t-butylcumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2, Like 5-di (t-butylperoxy) hexyne-3 Dialkyl peroxides; 2,2-bis
• azo compound examples include azobisisobutyronitrile, 2,2′-azobis (2-methylisobutyronitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), dimethyl-2,2 ′. -Azobis (isobutyrate), 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile) and the like.
• a commercial item can be used for a thermal radical polymerization initiator.
• the thermal radical polymerization initiator is preferably an organic peroxide from the viewpoint of stability and harmfulness, and peroxyesters are particularly preferable.
• the organic peroxide preferably has a one-hour half-life temperature of 50 to 110 ° C., which is an index of deactivation of the organic peroxide, from the viewpoint of the balance between the stability of the composition and the curing temperature. .
• the thermal radical polymerization initiator may be used alone or in combination of two or more.
• the composition can contain further components as long as the effects of the present invention are not impaired. Additional components include plasticizers, coupling agents, polymerization inhibitors, adhesion promoters, antioxidants, antifoaming agents, pigments, fillers, chain transfer agents, light stabilizers, surface tension modifiers, leveling agents, and ultraviolet rays. 1 or more types selected from the group which consists of an absorber and a foam suppressor are mentioned. These may be components known to those skilled in the art in the field of ink jet coating compositions.
• the viscosity of the composition is 150 mPa ⁇ s or less. Since it is such a low-viscosity composition, it can be applied on a substrate with a thin film thickness.
• the viscosity of the composition is preferably 100 mPa ⁇ s or less, and particularly preferably 80 mPa ⁇ s or less.
• the lower limit of the viscosity of the composition is not particularly limited as long as it is a value at which inkjet coating is possible, and may be equal to or lower than the viscosity measurable with a viscometer.
• the viscosity of the composition may be, for example, 1 mPa ⁇ s or more.
• the viscosity is a value measured with a cone plate viscometer at 25 ° C. under atmospheric pressure.
• the content of Component A is preferably 30 parts by weight or less, more preferably 20 parts by weight or less, and particularly preferably 10 parts by weight or less with respect to 100 parts by weight of Component A and Component B in total.
• the content of Component A is in the above range, the viscosity of the composition can be efficiently lowered and the adhesive strength tends to be more excellent.
• the content of the radical photopolymerization initiator is preferably 0.1 to 20 parts by weight, and preferably 0.5 to 15 parts by weight, with respect to 100 parts by weight as a total of Component A and Component B. Is more preferably 0.5 to 10 parts by mass.
• the content of the radical photopolymerization initiator is within the above range, the composition can be cured efficiently by irradiation with energy rays.
• the content of the thermal radical polymerization initiator is preferably 0.01 to 15 parts by weight, and preferably 0.1 to 10 parts by weight, with respect to 100 parts by weight as a total of Component A and Component B. More preferably, the amount is 0.5 to 5 parts by mass.
• content of a thermal radical polymerization initiator is the said range, hardening of a composition can be advanced efficiently by heating.
• the total content of the other components is preferably 0.01 to 15 parts by mass, and preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the total of component A and component B. More preferred is 1 to 5 parts by mass.
• the curable component is preferably composed of only component A and component B.
• the composition does not contain any additional curable components other than component A and component B such as epoxy resin.
• the curable component refers to a component that is polymerized and cross-linked by light irradiation and heating.
• the production method of the composition can be obtained by a production method comprising a step of mixing component A, component B, component C and optionally further components.
• the mixing method is not particularly limited, and various metals, plastic containers, stirring blades, a stirrer, and the like can be used.
• composition contains a radical photopolymerization initiator
• the composition can be cured with energy rays.
• the composition contains a thermal radical polymerization initiator
• the composition can be cured by heating.
• the composition contains a photoradical polymerization initiator and a thermal radical polymerization initiator
• the composition can be cured by energy rays and / or heating.
• the energy rays are not particularly limited, and active energy rays such as visible light, ultraviolet rays, X-rays, and electron beams can be used.
• the energy ray is preferably ultraviolet light.
• a light source that emits ultraviolet light (UV) can be used.
• UV ultraviolet light
• Examples of the ultraviolet light source include a metal halide lamp, a high-pressure mercury lamp, a xenon lamp, a mercury xenon lamp, a halogen lamp, a pulse xenon lamp, and an LED.
• the energy rays are preferably irradiated so that the integrated light amount of the energy rays is 500 to 10,000 mJ / cm 2 .
• Integrated light quantity is, and even more preferably preferably 1,000 ⁇ 6,000mJ / cm 2 at 1,000 ⁇ 8,000mJ / cm 2.
• the heating temperature and the heating time are not particularly limited as long as the composition is thermally cured and the temperature and time at which the substrates are bonded to each other.
• the heating temperature is preferably 70 to 120 ° C, more preferably 80 to 110 ° C.
• the heating time is preferably 10 minutes to 2 hours, more preferably 20 minutes to 100 minutes.
• the composition can be used as a composition for forming a cured product on a substrate and an adhesive for bonding the substrates together, and can be preferably used as an adhesive.
• the spin coater, die coater, dispenser, ink jet application (ink jet printing), screen printing and gravure printing can be used as a composition for one or more methods selected from the group consisting of: preferably an ink jet coating composition. Therefore, the composition is more preferably used as an adhesive for bonding substrates by inkjet coating.
• the manufacturing method of the laminated body obtained by bonding together base materials using a composition is demonstrated below.
• the manufacturing method of a laminated body contains the following process (A), (B) and (C).
• a step of applying a curable resin composition to the substrate 1 to form a curable resin composition layer (B) The process of bonding the base material 2 on a cured resin layer, and obtaining a bonded body, and (C) The process of heating a bonded body and / or irradiating an energy ray, and obtaining a laminated body.
• the base material 1 and the base material 2 are adhere
• the substrate 1 and the substrate 2 include an inorganic substrate, an organic substrate, and a substrate made of a mixture of inorganic and organic.
• the inorganic base material include one or more selected from the group consisting of glass, metal, and ceramic.
• the organic substrate include plastic.
• the substrate 1 and the substrate 2 may be the same substrate or different substrates.
• the laminated body may contain the further base material, and the adhesion method of the base material is not specifically limited.
• the base material 1 and the base material 2 may be a light transmissive member or a member that does not transmit light.
• the light-transmitting member only needs to have light transmittance according to the purpose of the laminated body. For example, when the laminated body is an image display device, visible light transmission is such that an image formed on the display body is visible. What is necessary is just to have sex.
• the light transmissive member include glass, (meth) acrylic resin, polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyester, cycloolefin polymer, and other plate-like materials and sheet-like materials.
• a light shielding layer may be formed on the light transmissive member. Examples of such a light transmissive member include an icon sheet and a decorative board.
• the member that does not transmit light is not particularly limited as long as it is an organic material that does not transmit light, an inorganic material that does not transmit light, or a combination thereof.
• the member that does not transmit light include a plate-like material or sheet-like material made of ceramics such as alumina, a metal sheet such as stainless steel subjected to an insulation treatment such as surface oxidation, a plate-like material made of thermosetting resin, thermoplastic resin, A sheet-like material is mentioned.
• Specific examples of such a member that does not transmit light include a liquid crystal display panel, an organic EL display panel, a protection panel, a touch panel, an organic EL element, and a member on which a color filter has already been formed.
• laminates that are various image display devices can be manufactured.
• Specific embodiments are as follows. (1) A liquid crystal display device can be manufactured by using one of the substrate 1 or the substrate 2 as a liquid crystal display panel and the other as a light-transmitting member. (2) A so-called top emission type organic EL display device can be manufactured by using one of the substrate 1 and the substrate 2 as an organic EL display panel and the other as a light-transmitting member.
• a so-called bottom emission type organic EL display device can be manufactured by using one of the substrate 1 and the substrate 2 as an organic EL display panel and the other as a member that does not transmit light.
• An image display device with a protection panel or a substrate with a protection panel can be manufactured by using one of the base material 1 or the base material 2 as a protection panel and the other as an image display device or various substrates. it can. Furthermore, one of the substrate 1 and the substrate 2 can be a protective panel and the other can be a light transmissive member.
• a touch panel can be manufactured by using one of the substrate 1 or the substrate 2 as a light-transmitting substrate on which a transparent electrode is formed and the other as a light-transmitting member. Furthermore, one of the substrate 1 or the substrate 2 can be a touch panel, and the other can be a light transmissive member.
• one of the base material 1 and the base material 2 is a liquid crystal display panel, an organic EL display panel, a protective panel, or a touch panel, and the other is a light transmissive member or a member that does not transmit light. Can be.
• the method for producing a laminate is preferably a combination of a base material 1 and a base material 2 in which one is an inorganic material and the other is an organic material, such as glass, polyimide or a combination thereof.
• a combination of a base material on which a color filter is laminated and a base material in which an element such as EL and a protective film are laminated in this order on a base material made of glass, polyimide, or a combination thereof is more preferable.
• the light and thermosetting resin composition is preferably applied on a base material on which a color filter is laminated.
• Step (A) is a step of forming a curable resin composition layer by applying light and a thermosetting resin composition to the substrate 1.
• the method of applying the composition to the substrate 1 is not particularly limited, and examples thereof include one or more methods selected from the group consisting of spin coater, die coater, dispenser, inkjet printing, screen printing, and gravure printing. Inkjet printing is preferred.
• the thickness of the curable resin composition layer formed by applying the composition is not particularly limited, and can be, for example, 10 to 500 ⁇ m, and preferably 30 to 350 ⁇ m.
• a process (B) is a process of bonding the base material 2 on a curable resin composition layer, and obtaining a bonded body.
• the substrate 2 can be placed on the substrate 1 on which the curable resin composition layer is formed so as to be in contact with the curable resin composition layer, and the substrate 1 and the substrate 2 can be bonded together.
• the step (B) may include a step of pressurizing a bonded body including the base material 1 and the base material 2 and a resin layer therebetween. Thereby, the adhesive force of the bonded body can be improved.
• the pressure treatment can be performed using a rubber roller, a flat plate press device or the like.
• a process (C) is a process of heating a bonded body and / or irradiating an energy ray, and obtaining a laminated body.
• the curable resin composition layer between the substrate 1 and the substrate 2 is cured, and the substrates are bonded to each other.
• the base material 1 is a base material which permeate
• an energy ray may be irradiated to the curable resin composition layer from the base material 1 side, and a cured resin layer may be formed.
• the cured resin layer may be formed by irradiating energy rays from the composition layer side.
• the base material 1 is a base material that does not transmit energy rays
• the curable resin composition layer is irradiated with energy rays from the curable resin composition layer side to form a cured resin layer.
• the base material 1 may not transmit light (not transmit visible light), but may transmit energy rays (for example, ultraviolet rays), and may transmit light (transmit visible light). (For example, ultraviolet rays) may not be transmitted.
• the manufacturing method of a laminated body can be used for adhesion
• the use of the laminate includes an image display device such as a liquid crystal.
• the laminate can be used for bonding the base material 1 and the base material 2 in which the base material 1 and the base material 2 are both formed with members that do not transmit light or elements and filters that do not transmit light.
• the use of the laminate includes an image display device such as an organic EL.
• each component other than the thermal radical polymerization initiator is weighed in a container (material SUS), and three-one motor at 60 to 80 ° C. under atmospheric pressure. (Shinto Kagaku Co., Ltd.) was used and stirred at 200 rpm for 30 minutes to 1 hour. Then, after confirming that the temperature of the composition had returned to 25 ° C., the thermal radical polymerization initiator was weighed and uniformly mixed using a three-one motor at 25 ° C. under atmospheric pressure.
• the light or thermosetting resin compositions of -12 and Comparative Examples 1-4 were prepared.
• PI film (Kapton manufactured by Toray Industries, Inc., thickness 50 ⁇ m), which was dropped on a slide glass (S1127 manufactured by Matsunami Glass Co., Ltd.) by dropping 0.2 g of the curable resin composition described in Table 1 to Table 3 And a rubber roller (SN-printing rubber roller No. 1), while applying a force of about 1 kg, the film was reciprocated five times on the film to extend the liquid onto the substrate.
• the curable resin compositions of Examples 1 to 3, 7, 9, and 11 and Comparative Examples 1 and 2 to which a photoradical polymerization initiator was added were metal halide lamps (ECS-301 manufactured by Eye Graphics). Was cured by irradiation with light of 3000 mJ / cm 2 .
• the curable resin compositions of Examples 4 to 6, 8, 10, and 12, and Comparative Examples 3 and 4 to which a thermal radical polymerization initiator was added were 100 ° C. for 30 minutes in an oven (LC113 manufactured by ESPEC). Cured by heating. Using these test pieces, a 180 ° peel test was conducted with a tensile tester (TG-2kN manufactured by Minebea) at a tensile speed of 60 mm / min. The average value was calculated after peeling off about 40 mm.
• the peel strength was high and the adhesive strength between the inorganic substrate and the organic substrate was excellent.
• the higher the molecular weight of the oligomer the higher the peel strength.
• the peel strength was increased by thermosetting.
• the peel strength increased as the content of Component A decreased.
• the composition containing component (B) having a short alkyl chain and a branched (meth) acrylic monomer has a long alkyl chain and Compared to a composition containing a “linear” (meth) acrylic monomer, the peel strength was higher.
• Comparative Examples 1 to 4 since an oligomer having a molecular weight of 3,000 was used, the peel strength was low, and the adhesive strength between the inorganic substrate and the organic substrate was inferior.
• the composition is excellent in the adhesive strength between an inorganic material and an organic material, it can be preferably used as an adhesive for bonding substrates for inkjet coating, and has high industrial utility.

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