CN107406722B - Photocurable adhesive composition - Google Patents

Photocurable adhesive composition Download PDF

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Publication number
CN107406722B
CN107406722B CN201680019262.XA CN201680019262A CN107406722B CN 107406722 B CN107406722 B CN 107406722B CN 201680019262 A CN201680019262 A CN 201680019262A CN 107406722 B CN107406722 B CN 107406722B
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meth
acrylate
adhesive composition
photocurable adhesive
laminate
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CN107406722A (en
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金子圣
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Kyoritsu Chemical and Co Ltd
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Kyoritsu Chemical and Co Ltd
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B38/00—Ancillary operations in connection with laminating processes
    • B32B38/0008—Electrical discharge treatment, e.g. corona, plasma treatment; wave energy or particle radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives

Abstract

The present invention relates to a photocurable adhesive composition which can provide a laminate having an adhesive strength equivalent to that in the absence of oxygen even when irradiated with light in the presence of oxygen, the photocurable adhesive composition comprising (a) a (meth) acrylate oligomer, (B) a monofunctional (meth) acrylate monomer, (C) a di-to tetrafunctional (meth) acrylate monomer, (D) a photoreaction initiator, (E) a tackifier having a softening point of 70 to 150 ℃, and (F) a liquid plasticizer.

Description

Photocurable adhesive composition
Technical Field
The present invention relates to a photocurable adhesive composition, a laminate using the photocurable adhesive composition, an optical display using the photocurable adhesive composition, and a method for producing the laminate.
Background
In recent years, in an image display device used in a smartphone or the like, from the viewpoint of preventing a reduction in visibility due to surface reflection, the following operations are performed: directly bonding a display body such as a liquid crystal display panel or an organic EL panel to a touch panel; alternatively, the display body and a front panel such as a protective panel or the touch panel and the front panel are bonded for reinforcement. The following methods are known as methods for manufacturing an image display device: after applying a photocurable resin composition to one substrate to be bonded, a temporary cured resin layer of the photocurable resin composition is formed by irradiation with ultraviolet rays, and then the other substrate is bonded (patent document 1).
However, in the type of radical polymerization of an acrylic resin generally used in a photocurable resin composition, the surface curability is poor due to inhibition of curing by oxygen in the air, and thus there is a problem that insufficiently cured components remain on the surface and the adhesive strength is reduced. In contrast, patent document 2 discloses the following method: the photocurable resin composition containing polyisoprene methacrylate oligomer, dicyclopentenyloxyethyl methacrylate and lauryl methacrylate is irradiated with ultraviolet rays under reduced pressure or in an inert gas atmosphere such as nitrogen.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2013-151151
Patent document 2: japanese patent laid-open publication No. 2013-254189
Disclosure of Invention
Problems to be solved by the invention
However, in the method described in patent document 2, in order to eliminate the influence of the inhibition of curing by oxygen, it is necessary to introduce a device for providing a reduced pressure or an inert gas atmosphere.
Accordingly, an object of the present invention is to solve the above problems and to provide a photocurable adhesive composition that can provide a laminate having an adhesive strength equivalent to that in the absence of oxygen even when irradiated with light in the presence of oxygen.
Means for solving the problems
The present invention has the following configuration.
[1] A photocurable adhesive composition comprising (A) a (meth) acrylate oligomer, (B) a monofunctional (meth) acrylate monomer, (C) a di-to tetrafunctional (meth) acrylate monomer, (D) a photoreaction initiator, (E) a tackifier having a softening point of 70 to 150 ℃, and (F) a liquid plasticizer.
[2] The photocurable adhesive composition according to [1], wherein the component (A) is at least 1 selected from the group consisting of (hydrogenated) polyisoprene, (hydrogenated) polybutadiene and (meth) acrylate oligomer having a polyurethane structure in the skeleton.
[3] The photocurable adhesive composition according to [1] or [2], wherein the component (C) is at least 1 selected from the group consisting of pentaerythritol tetra (meth) acrylate, tetra (meth) acrylate of an alkylene oxide adduct of pentaerythritol, trimethylolpropane tri (meth) acrylate, tri (meth) acrylate of an alkylene oxide adduct of trimethylolpropane, and nonanediol di (meth) acrylate.
[4] A laminate bonded with the photocurable adhesive composition according to any one of [1] to [3 ].
[5] The laminate according to [4], which is an optical display.
[6] A method for producing a laminate, comprising the following steps (I) to (III):
(I) a step of forming a photocurable adhesive composition layer on the substrate 1 by applying the photocurable adhesive composition according to any one of [1] to [3 ];
(II) irradiating the photocurable adhesive composition layer obtained in step (I) with an energy ray to form a cured product of the photocurable adhesive composition; and
(III) bonding the substrate 2 to the cured product obtained in the step (II).
[7] The production method according to [6], wherein the reaction rate of the photocurable adhesive composition in the cured product formed in the step (II) is 90% or more.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, there is provided a photocurable adhesive composition capable of providing a laminate having an adhesive strength equivalent to that in the absence of oxygen even when irradiated with light in the presence of oxygen.
Detailed Description
(Photocurable adhesive composition)
The photocurable adhesive composition comprises (A) a (meth) acrylate oligomer, (B) a monofunctional (meth) acrylate monomer, (C) a di-to tetrafunctional (meth) acrylate monomer, (D) a photoreaction initiator, (E) a tackifier having a softening point of 70 to 150 ℃, and (F) a liquid plasticizer. In the present specification, "(meth) acrylate" includes both "acrylate" and "methacrylate". In addition, "(meth) acryl" includes both "acryl" and "methacryl".
< A (meth) acrylate oligomer >
(A) The (meth) acrylate oligomer has 1 or more (meth) acryloyl groups in the molecule. (A) The (meth) acrylate oligomer is a base polymer in the photocurable adhesive composition. (A) The molecular weight of the (meth) acrylate oligomer is 1,000 to 100,000, preferably 10,000 to 70,000, and more preferably 20,000 to 50,000. When the molecular weight of the oligomer is 10,000 or more, the elastic modulus tends to be lowered and the flexibility tends to be improved; when the molecular weight of the oligomer is 70,000 or less, the viscosity tends not to be excessively increased, and the workability tends to be improved. In the present specification, the molecular weight is a weight average molecular weight measured by Gel Permeation Chromatography (GPC) and converted by a calibration curve of standard polystyrene.
The functional number ((number of (meth) acryloyl groups) of the (meth) acrylate oligomer (a) is not particularly limited, and is preferably two or more, and particularly preferably two to four functional. When the functional number of the (meth) acrylate oligomer (a) is two or more, sufficient curability and film-forming properties can be obtained. When the functional number of the (meth) acrylate oligomer (a) is four or less, the increase in elastic modulus associated with the increase in functional number can be suppressed.
The (meth) acrylate oligomer (a) is not particularly limited, and examples thereof include (meth) acrylate oligomers having (hydrogenated) polyisoprene, (hydrogenated) polybutadiene, or polyurethane in the skeleton. These (meth) acrylate oligomers may be used alone or in combination of two or more. Here, the (hydrogenated) polyisoprene comprises polyisoprene and/or hydrogenated polyisoprene, and the (hydrogenated) polybutadiene comprises polybutadiene and/or hydrogenated polybutadiene.
Examples of the (meth) acrylate oligomer having (hydrogenated) polybutadiene in the skeleton include (hydrogenated) polybutadiene (meth) acrylate and (hydrogenated) polybutadiene urethane (meth) acrylate. Examples of commercially available (meth) acrylate oligomers having (hydrogenated) polybutadiene in the skeleton thereof include TE2000 (manufactured by Nippon Petroleum Co., Ltd.: molecular weight: 2,000).
Examples of the (meth) acrylate oligomer having a (hydrogenated) polyisoprene in the skeleton include (hydrogenated) polyisoprene (meth) acrylate and (hydrogenated) polyisoprene urethane (meth) acrylate. As a commercially available product of the (meth) acrylate oligomer (A) having a (hydrogenated) polyisoprene in the skeleton, UC (manufactured by KURARAY Co., Ltd.: molecular weight: 25,000) and the like can be mentioned.
Examples of the (meth) acrylate oligomer having a urethane in the skeleton include polyether type, polycarbonate type, polyester type, or a combination thereof. Commercially available (meth) acrylate oligomers having a urethane (a) in the skeleton include UA (manufactured by Light Chemical), UV3630ID80 (manufactured by japan synthetic Chemical industries), UV3700B (manufactured by japan synthetic Chemical industries), and the like.
(A) The (meth) acrylate oligomer is preferably a (meth) acrylate oligomer having a polyurethane in the skeleton. (A) The number of the (meth) acrylate oligomer may be 1, or 2 or more thereof may be used in combination.
< (B) monofunctional (meth) acrylate monomer >
(B) The monofunctional (meth) acrylate monomer is a component capable of reducing the viscosity of the photocurable adhesive composition without impairing the reactivity of the (meth) acrylate oligomer (a) and the difunctional to tetrafunctional (meth) acrylate monomer (C).
(B) The monofunctional (meth) acrylate monomer is not particularly limited as long as it is a (meth) acrylate compound having 1 (meth) acryloyl group in the molecule, and examples thereof include alkyl (meth) acrylates, alkoxy-substituted alkyl (meth) acrylates, hydroxy-substituted alkyl (meth) acrylates, (meth) acrylates containing a hydroxyl group other than hydroxy-substituted alkyl (meth) acrylates, aromatic (meth) acrylates, and alicyclic (meth) acrylates.
Examples of the alkyl (meth) acrylate include 2-ethylhexyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and isostearyl (meth) acrylate. Examples of the alkoxy-substituted alkyl (meth) acrylate include methoxyethyl (meth) acrylate and the like. Examples of the hydroxy-substituted alkyl (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Examples of the hydroxyl group-containing (meth) acrylate other than the hydroxyl-substituted alkyl (meth) acrylate include 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, and the like. Examples of the aromatic (meth) acrylate include benzyl (meth) acrylate and phenyl (meth) acrylate. Examples of the alicyclic (meth) acrylate include dicyclopentadienyloxyethyl (meth) acrylate, norbornene (meth) acrylate, dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate, and the like.
(B) The monofunctional (meth) acrylate monomer is preferably 1 or more selected from the group consisting of alkyl (meth) acrylates and hydroxy-substituted alkyl (meth) acrylates.
(B) The monofunctional (meth) acrylate monomer has a molecular weight of less than 1,000. (B) The monofunctional (meth) acrylate monomer may be 1 type, or 2 or more types may be used in combination. When 2 or more (B) monofunctional (meth) acrylate monomers are used in combination, a combination of an alkyl (meth) acrylate and a hydroxy-substituted alkyl (meth) acrylate is preferable.
The content of the monofunctional (meth) acrylate monomer (B) in the photocurable adhesive composition is preferably 1 to 250 parts by mass, more preferably 20 to 200 parts by mass, still more preferably 30 to 150 parts by mass, and particularly preferably 40 to 90 parts by mass, based on 100 parts by mass of the (meth) acrylate oligomer (a).
< di-to tetrafunctional (meth) acrylate monomer >
(C) The di-to tetrafunctional (meth) acrylate monomer is a (meth) acrylate compound having 2 to 4 (meth) acryloyl groups in the molecule. (C) The di-to tetrafunctional (meth) acrylate monomer has an effect of improving the reactivity of the (meth) acrylate by increasing the functional group density, and this component can be in a sufficiently crosslinked state even in a state of being inhibited by the presence of oxygen. (C) The functional number of the component may be appropriately selected depending on the purpose.
Examples of the difunctional (meth) acrylate monomer include aliphatic di (meth) acrylates such as ethylene glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and the like; and alicyclic di (meth) acrylates such as dicyclopentanyl di (meth) acrylate and caprolactone-modified dicyclopentenyl di (meth) acrylate. The number of the bifunctional (meth) acrylate monomers may be 1, or 2 or more may be used in combination.
Examples of the trifunctional (meth) acrylate monomer include aliphatic tri (meth) acrylates such as trimethylolpropane tri (meth) acrylate and pentaerythritol tri (meth) acrylate; tri (meth) acrylate of alkylene oxide adduct of polyhydric alcohol such as tri (meth) acrylate of alkylene oxide adduct of trimethylolpropane and tri (meth) acrylate of alkylene oxide adduct of pentaerythritol.
Examples of the alkylene oxide in the alkylene oxide adduct include alkylene oxides having 2 to 4 carbon atoms such as ethylene oxide, propylene oxide, and butylene oxide, and ethylene oxide is preferable. The number of moles of alkylene oxide added is preferably 0.1 to 10 moles, more preferably 0.5 to 2 moles, based on 1 mole of hydroxyl group of the polyol.
The trifunctional (meth) acrylate monomer may be used in an amount of 1 kind, or 2 or more kinds may be used in combination.
Examples of the tetrafunctional (meth) acrylate monomer include aliphatic tetra (meth) acrylates such as pentaerythritol tetraacrylate and bis (trimethylolpropane) tetraacrylate; and tetra (meth) acrylates of alkylene oxide adducts of polyhydric alcohols such as tetra (meth) acrylate of alkylene oxide adducts of pentaerythritol and tetra (meth) acrylate of alkylene oxide adducts of bis (trimethylolpropane). Here, the alkylene oxide adduct includes the preferable one as described above in the trifunctional (meth) acrylate monomer. The tetrafunctional (meth) acrylate monomer may be 1 type, or 2 or more types may be used in combination.
(C) The difunctional to tetrafunctional (meth) acrylate monomers have a molecular weight of less than 1,000. (C) The di-to tetrafunctional (meth) acrylate monomer is preferably 1 or more selected from the group consisting of aliphatic di (meth) acrylates, aliphatic tri (meth) acrylates, tri (meth) acrylates of alkylene oxide adducts of polyols, tetra (meth) acrylates of alkylene oxide adducts of aliphatic tetra (meth) acrylates and polyols, and more preferably 1 or more selected from the group consisting of pentaerythritol tetra (meth) acrylate, tetra (meth) acrylates of alkylene oxide adducts of pentaerythritol, trimethylolpropane tri (meth) acrylate, tri (meth) acrylates of alkylene oxide adducts of trimethylolpropane, and nonanediol di (meth) acrylate. The (C) bifunctional to tetrafunctional (meth) acrylate monomer may be at least 1 selected from the group consisting of aliphatic di (meth) acrylates, tri (meth) acrylates and aliphatic tetra (meth) acrylates of alkylene oxide adducts of polyols, and may be a bifunctional to tetrafunctional aliphatic (meth) acrylate. (C) The number of the di-to tetrafunctional (meth) acrylate monomers may be 1, or 2 or more may be used in combination.
The content of the (C) bifunctional to tetrafunctional (meth) acrylate monomer in the photocurable adhesive composition is preferably 0.1 to 25 parts by mass, more preferably 1 to 20 parts by mass, and particularly preferably 3 to 10 parts by mass, based on 100 parts by mass of the (meth) acrylate oligomer (a). When the content of the (C) di-to tetrafunctional (meth) acrylate monomer is 0.1 part by mass or more per 100 parts by mass of the (a) (meth) acrylate oligomer, the adhesive strength is further improved, and when the content is 25 parts by mass or less, the increase in elastic modulus can be suppressed.
[ photo-reaction initiator (D) ]
The photoreaction initiator (D) is not particularly limited, and examples thereof include 1- [4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 1-hydroxy-cyclohexyl-phenyl-one, benzophenone, 2-dimethoxy-1, 2-diphenylethan-1-one, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, 2,4, 6-trimethylbenzoylphenylethoxyphosphine oxide, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and mixtures thereof, 2-methyl-1- [ 4-methylthio ] phenyl ] -2-morpholinopropan-1-one, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin isopropyl ether, bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide, 2-hydroxy-2-methyl- [4- (1-methylvinyl) phenyl ] propanol oligomer, 2-hydroxy-2-methyl-1-phenyl-1-propanone, isopropylthioxanthone, methyl o-benzoylbenzoate, [4- (methylthio) phenyl ] phenylmethane, methyl-N-propylthioxanthone, methyl-N-propylbenzoate, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, benzophenone, ethylanthraquinone, benzophenone ammonium salt, thioxanthone ammonium salt, bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethyl-pentylphosphine oxide, 2,4, 6-trimethylbenzophenone, 4-methylbenzophenone, 4,4 ' -bis (diethylamino) benzophenone, 1, 4-dibenzoylbenzene, 10-butyl-2-chloroacridone, 2 ' -bis (o-chlorophenyl) -4,5,4 ', 5 ' -tetrakis (3,4, 5-trimethoxyphenyl) -1,2 ' -biimidazole, 2,2 '-bis (o-chlorophenyl) -4,5, 4', 5 '-tetraphenyl-1, 2' -biimidazole, 2-benzoylnaphthalene, 4-benzoylbiphenyl, 4-benzoyldiphenyl ether, acryloylbenzophenone, bis (. eta.5-2, 4-cyclopenta-1-yl) -bis (2, 6-difluoro-3- (1H-pyrrol-1-yl) -phenyl) titanium, o-methylbenzoylbenzoate, ethyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, activated tertiary amine, carbazole-benzophenone-based photopolymerization initiator, acridine-based photopolymerization initiator, triazine-based photopolymerization initiator, benzoyl-based photopolymerization initiator, and the like.
(D) The photoreaction initiator is preferably 1 or more selected from the group consisting of 1-hydroxy-cyclohexyl-phenyl-ketone and 2,4, 6-trimethylbenzoylphenylethoxyphosphine oxide.
(D) The number of the photoreaction initiator may be 1, or 2 or more types may be used in combination.
The amount of the (D) photoreaction initiator in the photocurable adhesive composition is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and still more preferably 1 to 10 parts by mass, based on 100 parts by mass of the (meth) acrylate oligomer (a).
< tackifier having softening point of 70 ℃ to 150 >
The photocurable adhesive composition contains (E) a tackifier (hereinafter also referred to as "(E) tackifier") having a softening point of 70 to 150 ℃. By including the tackifier (E) in the photocurable adhesive composition, the adhesive strength can be improved and the cured product can be softened, and the following property to an adherend can be improved.
The softening point of the tackifier (E) is preferably 75 to 130 ℃ and more preferably 80 to 120 ℃ from the viewpoint of adhesive strength and flexibility. The softening point is a value measured by the ring and ball method.
(E) The tackifier is not particularly limited as long as it satisfies the above softening point, and examples thereof include rosin ester resins such as disproportionated rosin ester, polymerized rosin ester, and (hydrogenated) rosin ester; acrylic resins such as acrylic polymers and acrylic copolymers; a silicone resin; terpene resins such as terpene resin, terpene phenol resin, modified terpene resin, and hydrogenated terpene resin; a thermoplastic elastomer; petroleum resin; alicyclic saturated hydrocarbon resins; rosin resins such as rosin phenol; xylene resins, and the like.
(E) The tackifier is preferably a rosin ester-based resin, and more preferably a hydrogenated rosin ester. The rosin ester resin can suppress the influence of an acid component on an adherend (for example, a wiring portion of a touch panel) because the carboxylic acid moiety of rosin is esterified. Further, the hydrogenated rosin ester can prevent coloring at the initial stage and when exposed to heat because the rosin is hydrogenated.
(E) The number of the tackifiers may be 1, or 2 or more may be used in combination.
The amount of the tackifier (E) in the photocurable adhesive composition may be 5 to 70% by mass, based on 100% by mass of the photocurable adhesive composition. Within this range, the amount of the reactive component is appropriate, and the coating property is excellent, and the effect of expressing the adhesive strength is also advantageous. The tackifier is preferably 10 to 60 mass%, more preferably 15 to 50 mass% of 100 mass% of the photocurable adhesive composition.
< (F) liquid plasticizer >
The photocurable adhesive composition contains (F) a liquid plasticizer. The liquid state means that the liquid state exhibits fluidity at 25 ℃ under atmospheric pressure, and examples thereof include a viscosity of 1000 pas or less (for example, a viscosity of 0.01 pas to 1,000 pas) by a cone-plate viscometer. By including (F) a liquid plasticizer in the photocurable adhesive composition, a cured product having a small elastic modulus and flexibility can be obtained.
Examples of the liquid plasticizer (F) include phthalic acid esters such as dibutyl phthalate, diisononyl phthalate, diheptyl phthalate, di (2-ethylhexyl) phthalate, diisodecyl phthalate, and butyl benzyl phthalate; alkyl esters of polycarboxylic acids (e.g., C3-C12 alkyl esters of polycarboxylic acids), such as dioctyl adipate, diisononyl adipate, dioctyl sebacate, diisononyl sebacate, and diisononyl 1, 2-cyclohexanedicarboxylate; phosphoric acid esters such as tricresyl phosphate and tributyl phosphate; trimellitic acid ester; alkyl esters of polyoxyalkylene glycols such as triethylene glycol bis (2-ethylhexanoate) (e.g., C3-C12 alkyl esters of diethylene glycol, triethylene glycol, or tetraethylene glycol); a rubber-based polymer or a rubber-based copolymer (for example, polyisoprene, polybutadiene, polybutene, hydrogenated products thereof, derivatives having hydroxyl groups introduced at both ends of hydrogenated products thereof, and the like); a thermoplastic elastomer; petroleum resin; alicyclic saturated hydrocarbon resins; terpene resins such as terpene resin, terpene phenol resin, modified terpene resin, and hydrogenated terpene resin; rosin resins such as rosin phenol; rosin ester resins such as disproportionated rosin ester resin, polymerized rosin ester resin, and (hydrogenated) rosin ester resin; xylene resins, and the like; acrylic resins such as acrylic polymers and acrylic copolymers. They are liquid.
As the (F) liquid plasticizer, a rosin ester-based resin (in particular, a liquid one) is preferable, and a hydrogenated rosin ester (in particular, a liquid one) is preferable.
(F) The number of the liquid plasticizers may be 1, or 2 or more of them may be used in combination.
The amount of the liquid plasticizer (F) in the photocurable adhesive composition may be 300 parts by mass or less based on 100 parts by mass of the tackifier (E) from the viewpoint of strength expression by the tackifier (E), and is preferably 10 to 250 parts by mass, more preferably 30 to 200 parts by mass, and particularly preferably 50 to 150 parts by mass from the viewpoint of adhesive strength and flexibility.
< further ingredients >
The photocurable adhesive composition may contain an adhesive imparting agent, an antioxidant, a defoaming agent, a pigment, a filler, a chain transfer agent, a light stabilizer, a surface tension adjusting agent, a leveling agent, an ultraviolet absorber, a foam inhibitor, and the like, as long as the effects of the present invention are not impaired. Further, 1 kind of the component may be used, or 2 or more kinds may be used in combination. The total content of the further components in the photocurable adhesive composition is preferably 0.01 to 15 parts by mass, more preferably 0.1 to 10 parts by mass, and still more preferably 1 to 5 parts by mass, based on 100 parts by mass of the (meth) acrylate oligomer (a).
< method for producing Photocurable adhesive composition >
The photocurable adhesive composition can be prepared by mixing the respective components. The method of mixing is not particularly limited, and various metals, plastic containers, stirring blades, and stirrers can be used.
< uses of Photocurable adhesive composition >
The photocurable adhesive composition can be used for bonding any substrate 1 to any substrate 2. The photocurable adhesive composition can be used for bonding any of the substrates 1 and 2 including the substrate irradiated with an energy ray in the presence of oxygen. The substrate 1 and the substrate 2 may be the same substrate or different substrates. At least one of the substrate 1 and the substrate 2 may be a light-transmissive member. Thus, the photocurable adhesive composition is irradiated with an energy ray (e.g., ultraviolet ray) from the side of the light-transmissive member, and a cured resin layer can be formed. Examples of the light-transmitting member include glass, (meth) acrylic resins, polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyesters, cycloolefin polymers, and the like.
The photocurable adhesive composition is preferably used for bonding a display to a touch panel, a display to a front panel, or a touch panel to a front panel. The optical display is obtained by bonding the display and the touch panel, the display and the front panel, or the touch panel and the front panel to each other using a photocurable adhesive composition.
Examples of the front panel include glass, engineering plastics, transparent plastic plates such as acrylic plates (which may be subjected to single-sided or double-sided hard coat treatment or AR coating treatment), polycarbonate plates, PET plates, and PEN plates. The front panel may also be used as a protective panel.
Examples of the touch panel include a resistive touch panel, a capacitive touch panel, an electromagnetic induction touch panel, and an optical touch panel.
Examples of the display include an LCD, an EL display panel, an EL illuminator, electronic paper, and a plasma display panel.
The front panel, the touch panel, and the display body may have a step difference, and may also have a light shielding portion. Here, the light shielding portion refers to a portion where energy rays (e.g., ultraviolet rays) necessary for curing are not irradiated to the photocurable adhesive composition applied to the adhesive surface.
(layered body)
A laminate obtained by bonding with a photocurable adhesive composition is also an object of the present invention. Specifically, the laminate is obtained by bonding an arbitrary substrate 1 and an arbitrary substrate 2 with a photocurable adhesive composition. The method for producing the laminate is not particularly limited, and a method for producing the laminate described later is preferred. The laminated body obtained by bonding with the photocurable adhesive composition is preferably an optical display.
(method for producing laminate)
A method for producing a laminate in which a substrate 1 and a substrate 2 are laminated via a cured product of a photocurable adhesive composition, comprising the following steps (I) to (III):
(I) a step of applying a photocurable adhesive composition to form a photocurable adhesive composition layer on the base material 1;
(II) irradiating the photocurable adhesive composition layer obtained in step (I) with an energy ray to form a cured product of the photocurable adhesive composition; and
(III) bonding the substrate 2 to the cured product obtained in the step (II).
In the method for producing a laminate, the photocurable adhesive composition, the substrate 1 and the substrate 2 are as described above, including the preferred embodiments. Thus, the method for producing the laminate is preferably a method for producing an optical display. The laminate obtained by the method for producing a laminate is preferably an optical display.
< Process (I) >
The step (I) is a step of forming a photocurable adhesive composition layer on the base material 1 by applying a photocurable adhesive composition.
The method of applying the photocurable adhesive composition to the substrate 1 is not particularly limited, and a method using a die coater, a dispenser (dispenser), screen printing, or the like can be used. The thickness of the photocurable adhesive composition layer is not particularly limited, and may be, for example, 10 to 500 μm, preferably 30 to 350 μm.
< step (II) >
The step (II) is a step of irradiating the photocurable adhesive composition layer obtained in the step (I) with an energy ray to form a cured product of the photocurable adhesive composition.
The energy ray is not particularly limited, and active energy rays such as visible rays, ultraviolet rays, X-rays, and electron rays can be used. The energy ray is preferably ultraviolet ray. As the light source of ultraviolet rays, a light source emitting ultraviolet rays (UV) can be used. Examples of the light source of ultraviolet rays 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 peak wavelength of the LED is not particularly limited, and examples thereof include 365nm, 405nm, 375nm, 385nm and 395 nm. Light emitted from a light source other than the LED may be adjusted to light of a specific wavelength by passing through a filter. Specifically, the adjustment can be performed by a filter that cuts light having a wavelength of 300nm or less and/or a filter that cuts light having a wavelength of 500nm or more.
The irradiation of the energy ray can be performed in accordance with the cumulative light amount of the energy ray of 30mJ/cm2～15,000mJ/cm2The irradiation is performed in the manner of (1). The cumulative light amount is preferably 50mJ/cm2～12,000mJ/cm2More preferably 100mJ/cm2～10,000mJ/cm2。
In the step (II), the energy ray is irradiated from the photocurable adhesive composition side to form a cured resin layer. Here, when the substrate 1 is a light-transmitting member, the energy ray may be irradiated to the photocurable adhesive composition from the light-transmitting member side to form a cured resin layer. The irradiation with the energy ray may be performed in the presence of oxygen, under reduced pressure, or in an inert gas atmosphere such as nitrogen.
The reactivity of the photocurable adhesive composition in the cured product formed in step (II) is not particularly limited, and is preferably 90% or more. If the reaction rate is 90% or more, sufficient strength can be exhibited even without further irradiation after bonding, and therefore, the process can be simplified. Further, the photocurable adhesive composition can be used without concern for penetration or damage to other members or bleeding of a cured product due to the uncured photocurable adhesive composition remaining, and can also be applied to a case where a light-impermeable light-shielding layer is provided in a laminate or bonding of substrates that are not light-permeable at all. The reactivity is defined by the reduction rate of (meth) acryloyl groups in the photocurable adhesive composition before and after irradiation with energy rays (e.g., ultraviolet rays), and can be measured by FT-IR. The total reaction of (meth) acryloyl groups in the photocurable adhesive composition was defined as 100%.
< step (III) >
The step (III) is a step of bonding the substrate 2 to the cured product obtained in the step (II) to obtain a laminate. The substrate 2 is placed on the substrate 1 on which the cured product has been formed so as to contact the cured product, and the substrate 1 and the substrate 2 can be bonded to each other. The substrate 2 is a substrate to which the photocurable adhesive composition is not applied in the step (I).
The method for producing a laminate may further include a step of subjecting a bonded body composed of the base material 1, the base material 2, and a cured product of the photocurable adhesive composition therebetween to a pressure treatment. The method for producing a laminate includes a pressure treatment, whereby the adhesive strength of the laminate is further improved. The pressing treatment may be performed by a rubber roller, a flat plate molding device, or the like.
Examples
The present invention will be described in more detail below with reference to examples and comparative examples. The present invention is not limited to these examples. The expression is part by mass or% by mass unless otherwise specified.
The components in the ratios shown in table 1 were uniformly mixed to prepare photocurable adhesive compositions of examples and comparative examples.
Using the obtained photocurable adhesive compositions of examples and comparative examples, the properties were measured as follows.
< elastic modulus >
The modulus of elasticity was determined as follows: a No.3 dumbbell test piece (thickness: 1mmt) was produced according to JIS Z1702 and measured at a rate of 10mm/min using a tensile compression tester (manufactured by Minebea, Technograph TG-2 kN). The dumbbell test pieces were produced as follows: a conveyer type metal halide lamp (200 mW/cm, manufactured by Eyegraphics Co., Ltd.) was used2) At 6,000mJ/cm2The photocurable adhesive composition is cured, and the resulting cured product is produced.
< OPEN (OPEN) strength and CLOSE (CLOSE) strength >
Open strength and closed strength test pieces were obtained as follows.
< open cured Strength measurement test piece >)
A spacer having a thickness of 150 μmt and made of 3 sheets of a transparent adhesive tape (50 μmt) was attached to a substrate 1(26 mm. times.75 mm. times.1.1 mmt, glass) so that the applied portion of the photocurable adhesive composition was 20mm wide, the photocurable adhesive composition was applied by a metal blade to form a photocurable adhesive composition layer, and then a conveyor-type metal halide lamp (200 mW/cm, manufactured by Eyegraphics Co., Ltd.)2) At a rate of 3,000mJ/cm2The photocurable adhesive composition is irradiated with light from the side of the photocurable adhesive composition layer to form a cured product of the photocurable adhesive composition. A substrate 3(26 mm. times.150 mm. times.0.1 mmt, PET) was placed on a cured product of the photocurable adhesive composition and bonded to obtain an open-cured strength measurement test piece.
< test piece for measuring Strength of Enclosed curing >)
A150 μmt thick spacer made of 3 sheets of a transparent adhesive tape (50 μmt) was attached to a base material 1(26 mm. times.75 mm. times.1.1 mmt, glass) so that the coated portion of the photocurable adhesive composition was 20mm wide, the photocurable adhesive composition was coated with a metal blade to form a photocurable adhesive composition layer, a base material 2(26 mm. times.75 mm. times.0.05 mmt, release PET) was placed on the photocurable adhesive composition layer and bonded, and then a conveyor-type metal halide lamp (200 mW/cm, manufactured by Eyegraphics corporation, was used2) At a rate of 3,000mJ/cm2The cured product of the photocurable adhesive composition was formed by irradiating light through the substrate 1. The substrate 2 was peeled, and a substrate 3(26mm × 150mm × 0.1mmt, PET) was placed on the surface from which the substrate 2 was peeled and bonded to obtain a seal-cured strength measurement test piece.
< measurement of open Strength and closed Strength >
The open strength and the closed strength were measured at a rate of 300mm/min using a tensile compression tester (manufactured by Minebea, Technograph TG-2 kN).
< Rate of Change of Strength >
The strength change rate of the open strength and the closed strength was determined. The steel plate was evaluated as "good" when the change rate of strength was 20% or less, and as "poor" when the change rate exceeded 20%.
< reaction Rate >
The reactivity of the photocurable adhesive composition in the cured product of the photocurable adhesive composition was measured by using FT-IR (Spectrum 100, manufactured by Perkin Elmer) as the reduction rate of acryloyl groups before and after irradiation with energy rays of the photocurable adhesive composition. A base line of 800 to 820cm in an FT-IR measurement chart of the photocurable adhesive composition layer before irradiation with energy rays-1Absorption peak height (X) of (2), and a base line of 800 to 820cm in an FT-IR measurement chart of a cured product of the photocurable adhesive composition after irradiation with an energy ray-1The absorption peak height (Y) of (a) is substituted into the following equation (1), thereby obtaining the reduction rate.
Reaction rate (%) { (X-Y)/X } × 100 · (1)
< measurement of reaction Rate of open curing >
A spacer having a thickness of 150 μmt and made of 3 sheets of a transparent adhesive tape (50 μmt) was attached to a substrate 1(26 mm. times.75 mm. times.1.1 mmt, glass) so that the applied portion of the photocurable adhesive composition was 20mm wide, the photocurable adhesive composition was applied by a metal blade to form a photocurable adhesive composition layer, and then a conveyor-type metal halide lamp (200 mW/cm, manufactured by Eyegraphics Co., Ltd.)2) At a rate of 3,000mJ/cm2The photocurable adhesive composition is irradiated with light from the side of the photocurable adhesive composition layer to form a cured product of the photocurable adhesive composition. A substrate 3(26 mm. times.150 mm. times.0.1 mmt, PET) was placed on a cured product of the photocurable adhesive composition and bonded to obtain an open-cured strength measurement test piece. The reaction rate of the photocurable adhesive composition was measured with respect to the cured product of the photocurable adhesive composition in the open-cured strength measurement test piece.
< measurement of reaction Rate of blocking curing >
The coating portion of the photocurable adhesive composition was 20mm wideA method comprising attaching a spacer having a thickness of 150 μmt made of 3 sheets of a transparent adhesive tape (50 μmt) to a substrate 1(26 mm. times.75 mm. times.1.1 mmt, glass), applying a photocurable adhesive composition with a metal blade to form a photocurable adhesive composition layer, placing a substrate 2(26 mm. times.75 mm. times.0.05 mmt, release PET) on the photocurable adhesive composition layer, bonding the layers, and using a conveyor-type metal halide lamp (200 mW/cm, manufactured by Eyegraphics Inc.)2) At a rate of 3,000mJ/cm2The cured product of the photocurable adhesive composition was formed by irradiating light through the substrate 1. The substrate 2 was peeled, and a substrate 3(26mm × 150mm × 0.1mmt, PET) was placed on the surface from which the substrate 2 was peeled and bonded to obtain a seal-cured strength measurement test piece. The reaction rate of the photocurable adhesive composition was measured with respect to the cured product of the photocurable adhesive composition in the seal-cured strength measurement test piece.
The results are summarized in Table 1.
[ Table 1]
Figure BDA0001421950340000151
UV3630ID 80: urethane acrylate (difunctional) (molecular weight 35,000, manufactured by Nippon synthetic chemical industries Co., Ltd.)
LA: acrylic acid lauryl ester
4-HBA: 4-Hydroxybutyl acrylate
A-TMMT: pentaerythritol tetraacrylate (tetra-functional) (NKESTER, manufactured by Xinzhongcun chemical industry Co., Ltd.)
A-TMPT-3 EO: trimethylolpropane triacrylate (ethylene oxide (EO) adduct) (trifunctional) (NK ESTER, molecular weight: 428, 3 moles of ethylene oxide units per 1 molecule, manufactured by Newzhongmu chemical industries, Ltd.)
1,9 ND-A: 1, 9-nonanediol diacrylate
I-184: 1-hydroxy-cyclohexyl-phenyl-ketones
I-TPO: 2,4, 6-trimethylbenzoyldiphenylphosphine oxide
KE 311: hydrogenated rosin ester (softening point 95 ℃ C.) (manufactured by Mitsukawa chemical Co., Ltd.)
ME-D: hydrogenated rosin ester (liquid state) (manufactured by Mitsukawa chemical Co., Ltd.)
The strength change ratios of examples 1 to 3 were 0 (i.e., there was no difference in strength between open curing and closed curing). That is, by including the di-to tetrafunctional (meth) acrylate monomer, the adhesive strength is equivalent to that in the absence of oxygen even when light irradiation is performed in the presence of oxygen. On the other hand, comparative example 1 does not contain a di-to tetrafunctional (meth) acrylate monomer, and therefore, the adhesive strength when light irradiation is performed in the presence of oxygen is reduced compared to the adhesive strength when light irradiation is performed in the absence of oxygen.
Industrial applicability
The photocurable adhesive composition is useful as a pressure-sensitive adhesive for a laminate, particularly an optical display and an optical display.

Claims (5)

1. A method for producing a laminate, comprising the following steps (I) to (III):
(I) a step of applying a photocurable adhesive composition to form a photocurable adhesive composition layer on the base material 1;
(II) irradiating the photocurable adhesive composition layer obtained in step (I) with an energy ray in the presence of oxygen to form a cured product of the photocurable adhesive composition; and
(III) a step of bonding the substrate 2 to the cured product obtained in the step (II),
wherein the reaction rate of the photocurable adhesive composition in the cured product formed in the step (II) is 90% or more,
the photo-curable adhesive composition includes (A) a (meth) acrylate oligomer having a molecular weight of 10,000 to 70,000, (B) a monofunctional (meth) acrylate monomer, (C) a di-to tetrafunctional (meth) acrylate monomer, (D) a photo-reaction initiator, (E) a tackifier having a softening point of 70 to 150 ℃, and (F) a liquid plasticizer.
2. The method for producing a laminate according to claim 1, wherein the component (A) is at least 1 selected from the group consisting of (hydrogenated) polyisoprene, (hydrogenated) polybutadiene and (meth) acrylate oligomers having a polyurethane structure in the skeleton.
3. The method for producing a laminate according to claim 1 or 2, wherein the component (C) is at least one member selected from the group consisting of pentaerythritol tetra (meth) acrylate, tetra (meth) acrylate of an alkylene oxide adduct of pentaerythritol, trimethylolpropane tri (meth) acrylate, tri (meth) acrylate of an alkylene oxide adduct of trimethylolpropane, and nonanediol di (meth) acrylate.
4. The method of producing a laminate as claimed in claim 1 or 2, wherein the laminate is an optical display.
5. The method of manufacturing a laminate according to claim 3, wherein the laminate is an optical display.
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