CN111108162A - Method for producing laminate containing curable bonding material - Google Patents
Method for producing laminate containing curable bonding material Download PDFInfo
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- CN111108162A CN111108162A CN201880059328.7A CN201880059328A CN111108162A CN 111108162 A CN111108162 A CN 111108162A CN 201880059328 A CN201880059328 A CN 201880059328A CN 111108162 A CN111108162 A CN 111108162A
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- bonding material
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- 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
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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
- 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
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Abstract
The present invention relates to a method for producing a laminate comprising an adherend (C1) and a bonding material (X), the method comprising, in order: a step [1] of activating a reaction site of the bonding material (X); a step [2] of attaching the bonding material (X) to an adherend (C1); and a step [3] of curing the bonding material (X). According to the present invention, a novel laminated body in which members are easily fixed and which can be constructed even at a low temperature in a short time can be manufactured, and therefore, the present invention can be used as a material for firmly bonding various members used exclusively for an image display device to each other.
Description
Technical Field
The present invention relates to a method for producing a laminate using a bonding material that can be used for lamination of members used in an image display device.
Background
In recent years, liquid crystal display devices have been widely used as display devices for televisions, smart phones, Personal Assistant Devices (PADs), tablet computers, car navigation systems, and the like.
As the liquid crystal display device, there is generally known a liquid crystal display device having a structure in which a liquid crystal display panel, a planar lighting device (backlight device) which illuminates the liquid crystal display panel while being superimposed on the back surface of the liquid crystal display panel, a circuit board (substrate) or a chassis on which other electronic components are mounted, a heat sink which diffuses heat generated by the components, and the like are laminated.
In order to laminate the members of the liquid crystal display device, a method of bonding two members to each other by interposing a bonding layer made of an adhesive such as an epoxy adhesive or a urethane adhesive between the members is often used for the purpose of firmly fixing the members to each other and preventing the members from falling off with time (for example, see patent document 1).
In the method of joining the members, for example, when the surfaces of the members to be laminated have a warp or a concave-convex, the method includes the following steps in order to remove the thickness unevenness of the coated surface after the adhesive is applied and the adhesive follows the warp or the concave-convex: the surface coated with the adhesive is smoothed by scraping the applied adhesive, and thereafter another member is laminated (for example, see patent document 2).
In the conventional production, an adhesive having a long curing time is required to ensure the working time required for the lamination step. As a result, a long curing process is required until the adhesive after the laminating process exhibits sufficient bonding strength.
As a method for accelerating the progress of curing of the adhesive after the lamination step, heat curing of the adhesive has been studied, but there is a possibility that a member of the liquid crystal display device is damaged by heat during curing. In addition, there are problems as follows: the bonding method using an adhesive has problems in that the members are deformed by strain between the members generated during cooling due to the difference in thermal expansion between the members, or the bonding material and the members are cracked and peeled off.
In addition, if an adhesive having excellent curability at room temperature is used in order to shorten the curing time, the time required for the lamination step cannot be secured, and since curing is performed before lamination, sufficient bonding strength may not be exhibited at the time of lamination.
In addition, as a method of completing curing at a low temperature in a short time, a bonding method by light irradiation has been studied, but the method cannot be used for members that do not transmit light, and application members are limited, and practical use is difficult.
In light of the above background, there is a strong demand for a novel joining method that can complete construction in a short time and at a low temperature and can suitably join even to a material that does not transmit light.
Documents of the prior art
Patent document
Patent document 1: japanese patent No. 5546136
Patent document 2: japanese patent laid-open publication No. 2003-136677
Disclosure of Invention
Problems to be solved by the invention
The present invention addresses the problem of providing a novel method for producing a laminate that can be applied in a short time and at a low temperature and can be appropriately joined to a material that does not transmit light.
Means for solving the problems
The present inventors have focused on a method for producing a laminate, and have made extensive studies to find: the above problems are solved by a production method comprising the following steps [1] to [3], and the present invention has been completed.
That is, the present invention is a method for producing a laminate comprising an adherend (C1) and a bonding material (X), the method comprising, in order: a step [1] of activating a reactive site of the bonding material (X); a step [2] of attaching the adhesive to an adherend (C1); and a step [3] of curing the bonding material (X).
ADVANTAGEOUS EFFECTS OF INVENTION
In the present invention, since the reactive site of the bonding material (X) is activated, the curing reaction of the bonding material (X) can be performed in a short time and at a low temperature.
In the present invention, since the reactive site of the bonding material (X) is activated and then can be bonded to the adherend (C1), the bonding material can be applied to various members such as members that do not transmit light.
Detailed Description
The production method of the present invention is a method for producing a laminate comprising an adherend (C1) and a bonding material (X), which comprises in this order: a step [1] of activating a reactive site of the bonding material (X); a step [2] of attaching the bonding material (X) to an adherend (C1); and a step [3] of curing the bonding material (X).
The production method of the present invention is capable of curing the bonding material (X) in a state in which the reactivity of the bonding material (X) is improved, because the bonding material (X) is activated and then attached to the adherend (C1). This enables curing at a lower temperature than in the state where activation is not performed. In addition, curing can be performed in a shorter time than in a state where activation is not performed.
In the production method of the present invention, the step of activating the reactive site of the bonding material (X) having a reactive site in the material is performed in the step [1 ]. The reactive site is a site that is activated by application of an external stimulus and is in a state of being able to react with another site.
The method for activating the reactive site of the bonding material (X) includes, but is not limited to, heat, light, moisture, and the like, and heat or light is preferably used, and light is more preferably used. The bonding material (X) activated by light has good storage stability, and can activate the reactive site at a low temperature. In addition, the external stimulus may be used alone or in combination of two or more.
Examples of the method for activating the reaction site by the light include photo radical polymerization, photo cation polymerization, and photo anion polymerization, and the use of photo cation polymerization or photo anion polymerization is preferable because it is not inhibited by oxygen at the time of curing and the reaction continues after the irradiation with light, and also, even in the case of a member which is not light-transmitting, the member can be laminated with an adherend after the irradiation with light to the bonding material. Further, cationic photopolymerization is more preferable because of excellent reactivity upon irradiation with light and easy attachability after curing. These polymerization methods may be used alone or in combination of two or more.
Further, a production method of the present invention is a method for producing a laminate including an adherend (C1) and an adherend (C2) with a bonding material (X) therebetween, the method including, in order: a step [01] of attaching the bonding material (X) to an adherend (C2); a step [1] of activating a reactive site of the bonding material (X); a step [2] of attaching the adhesive to an adherend (C1); and a step [3] of curing the bonding material (X), wherein at least one of the steps [01] and [1] and the steps [2] and [3] includes a step [02] of performing step following (curing step).
In the step of performing step following of the step [02], the step of attaching the bonding material (X) to the adherend (C1) and/or the adherend (C2) having a warp and/or an irregularity to fill the warp and/or the irregularity is performed.
Since the step [02] is initiated by performing the step [1] of activating the reactive site of the joining material (X), the step [02] is preferably performed after the step [01] and before the step [1] in order to sufficiently ensure a time (curing time) for the joining material to follow the deflection and/or the irregularity in height when the deflection and/or the irregularity exist in any of the adherends joined by the present production method.
The step [01] may include a step of heating the members to be laminated to the extent that the members are not damaged or the joining material flows without being excessively deformed. By including the heating step, when the bonding material (X) is bonded to the adherend (C2), the adhesive sheet can be more firmly adhered to obtain high bonding strength.
In the step [01], the heating is performed at a temperature of preferably 10 ℃ to 150 ℃, more preferably 20 ℃ to 120 ℃, still more preferably 30 ℃ to 100 ℃, and most preferably 40 ℃ to 90 ℃. By setting the range, it is possible to suppress damage to the member and to obtain high bonding strength by more firmly adhering while suppressing excessive deformation of the bonding material.
The step [02] may include a step of heating the members to be laminated to the extent that the members are not damaged or the joining material flows without being excessively deformed. By including the step of heating, the time required for the joining material (X) to follow the step can be shortened when the joining material (X) follows the adherend (C2) with the step, and the production method of the present invention can be completed in a short time.
In the step [02], the heating is preferably performed at a temperature of 20 ℃ to 150 ℃, more preferably 40 ℃ to 120 ℃, still more preferably 55 ℃ to 100 ℃, and most preferably 70 ℃ to 90 ℃. By setting the range, it is possible to perform the step following while suppressing damage to the members to be laminated and excessive deformation of the joining material during the step following.
The step [2] is preferably performed within 24 hours, more preferably within 12 hours, even more preferably within 3 hours, and most preferably within 1 hour after the step [1] is performed. By setting the range, the bonding material (X) can be more firmly adhered to the adherend (C1) when the bonding material (X) is attached to the adherend, and high bonding strength can be obtained.
In the step [2], the joining may be performed while heating within a range in which the members to be laminated are not damaged, the members are not deformed by strain generated between the members, or cracks are not generated between the joining material and the members. By including the step of heating, the bonding material (X) can be more firmly adhered to the adherend (C1) to obtain high bonding strength.
In the step [2], the heating is performed at a temperature of preferably 10 ℃ to 150 ℃, more preferably 20 ℃ to 120 ℃, still more preferably 30 ℃ to 100 ℃, and most preferably 40 ℃ to 80 ℃. By setting the range, it is possible to suppress damage of the member, and further, to obtain high bonding strength by suppressing excessive deformation of the bonding material and by more firmly adhering.
The step [3] includes a step of curing the bonding material (X). By curing the joining material (X), the joining material (X) and the adherend (C1) can be more firmly adhered to each other, and high joining strength can be obtained.
The step [3] may include a step of heating the laminate within a range in which the members to be laminated are not damaged, the members are not deformed by strain generated between the members, or cracks are not generated between the joining material and the members. By including the step of heating, the time required for curing the joining material (X) can be shortened after the joining material (X) and the adherend (C1) are laminated, and the production method of the present invention can be completed in a short time.
In the step [3], the heating is performed at a temperature of preferably 20 ℃ to 150 ℃, more preferably 40 ℃ to 120 ℃, still more preferably 55 ℃ to 100 ℃, and most preferably 70 ℃ to 90 ℃. By setting the range, it is possible to suppress damage to the members and prevent deformation of the members and cracks between the joining material and the members due to strain generated between the members.
The bonding material (X) is formed in the step [01]]The storage modulus at the time of sticking of (3) is preferably 5.0X 103Pa or more, more preferably 5.0X 104Pa～1.0×108Pa, more preferably 5.0X 105Pa～1.0×107Pa. By setting asIn the above range, the operation of the bonding material before curing is facilitated, and the bonding material is prevented from being deformed and flowing.
Further, as the bonding material (X), in the step [02]]Among them, the storage modulus of the bonding material (X) in the step following is preferably less than 5.0X 103Pa, more preferably 1.0X 103Pa or less, more preferably 1.0X 102Pa or less. By setting the above range, a bonding material having further improved conformability to the stepped portion can be obtained.
Said step [3]The storage modulus of the bonding material (X) at 25 ℃ is preferably 1.0X 105Pa or more, more preferably 1.0X 106Pa or more, more preferably 1X 108Pa or above. By setting the range, the bonding strength of the cured product of the bonding material (X) can be further improved.
The storage modulus of the bonding material (X) is a value measured at a frequency of 1.0 Hz.
As the bonding material (X) used in the production method of the present invention, a composition containing a polymerizable compound or the like described later, which is not particularly limited as long as polymerization is initiated by external stimulation, can be used.
As the bonding material (X), a material molded in a sheet shape in advance is preferably used in terms of excellent workability before curing and easy adjustment of thickness.
The sheet-like bonding material is preferably a bonding material having a thickness in the range of 50 to 2000. mu.m, more preferably 100 to 1000. mu.m, and most preferably 200 to 800. mu.m. By setting the range, the workability before curing is excellent, and the follow-up can be performed even for an article having a difference in height such as unevenness or deflection on the surface of the adherend.
The polymerizable compound preferably contains a thermally polymerizable compound or a photopolymerizable compound, but when a photopolymerizable compound is used, the storage stability of the bonding material (X) before the production step [1] is improved, and the reactive site can be activated at a low temperature, which is more preferable.
Examples of the photopolymerizable compound include a photoradically polymerizable compound, a photocationically polymerizable compound, and a photocationically polymerizable compound. These compounds may be used alone or in combination, and the use of a photocationic polymerizable compound or a photocationic polymerizable compound is preferable because the reaction continues after irradiation with light without being inhibited by oxygen at the time of curing, and the bonding material is laminated with an adherend after irradiation with light, whereby the bonding material can be laminated even on a member which does not transmit light. Further, the use of the cationically polymerizable compound is more preferable because it is excellent in reactivity after light irradiation and easy to obtain high adhesiveness after curing.
The cationic polymerizable compound is not particularly limited as long as it has one or more cationic polymerizable functional groups in one molecule. The photo cation polymerizable compound is preferably a compound having one or more cation polymerizable functional groups such as an epoxy group, an oxetanyl group, a hydroxyl group, a vinyl ether group, an episulfide group, a vinyl imine group, and an oxazoline group (oxazoline) in one molecule. Among them, a cationically polymerizable compound having an epoxy group is more preferable in terms of obtaining high curability and bonding strength after curing.
As the epoxy resin, a compound having one or more epoxy groups in one molecule can be used. Specifically, bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, biphenyl-type epoxy resin, tetramethylbiphenyl-type epoxy resin, polyhydroxynaphthalene-type epoxy resin, isocyanate-modified epoxy resin, 10- (2, 5-dihydroxyphenyl) -9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide-modified epoxy resin, phenol novolak-type epoxy resin, cresol novolak-type epoxy resin, hexanediol-type epoxy resin, triphenylmethane-type epoxy resin, tetraphenylethane-type epoxy resin, dicyclopentadiene-phenol addition reaction-type epoxy resin, phenol aralkyl-type epoxy resin, naphthol novolak-type epoxy resin, naphthol aralkyl-type epoxy resin, naphthol-phenol co-condensed novolak-type epoxy resin, naphthol aromatic alkyl-type epoxy resin, naphthol-phenol co-condensed novolak-type epoxy resin, phenol aldehyde, Naphthol-cresol co-condensed novolac type epoxy resin, aromatic hydrocarbon formaldehyde resin-modified phenol resin type epoxy resin, biphenyl-modified novolac type epoxy resin, trimethylolpropane type epoxy resin, alicyclic epoxy resin, acrylic resin having an epoxy group, polyurethane resin having an epoxy group, polyester resin having an epoxy group, epoxy resin having flexibility, and the like.
When an alicyclic epoxy resin or a polyfunctional aliphatic epoxy resin is used as the epoxy resin, the cationic polymerizability is excellent, and therefore a bonding material having excellent curability can be obtained.
Further, other resin components may be blended or added to the above-mentioned components to improve flexibility, or to improve adhesion or bending force, and as such a modified body, a carboxyl-terminated butadiene-acrylonitrile rubber (CTBN) modified epoxy resin; epoxy resins obtained by resin-dispersing various rubbers such as acrylic rubber, NBR, SBR, butyl rubber, and isoprene rubber; an epoxy resin modified with the liquid rubber; epoxy resins obtained by adding various resins such as acrylic acid, urethane, urea, polyester, and styrene; chelate-modified epoxy resin; polyol-modified epoxy resins, and the like.
Specific examples of the photocationically polymerizable compound having a cationically polymerizable functional group other than an epoxy group include: oxetane compounds such as 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene, 1, 4-bis [ (3-methyl-3-oxetanylmethoxy) methyl ] benzene, 3-methyl-3-glycidyloxybutane, 3-ethyl-3-glycidyloxybutane, 3-methyl-3-hydroxymethyloxetane, 3-ethyl-3-hydroxymethyloxetane and bis { 1-ethyl (3-oxetanyl) } methyl ether.
As the bonding material (X) used in the production method of the present invention, a bonding material containing other components in addition to the polymerizable compound as needed can be used.
As the bonding material (X) used in the production method of the present invention, a polymerization initiator that can react with the polymerizable compound is preferably used.
The polymerization initiator may be an initiator that is activated by an external stimulus, and for example, in the case of using a cationically polymerizable compound as the polymerizable compound, it is preferable to use an initiator having a functional group capable of reacting with the cationically polymerizable functional group.
The polymerization initiator includes a photopolymerization initiator and a thermal polymerization initiator, and may be used alone or in combination of two or more. Among them, in order to obtain a reaction at low temperature and a good curing reaction, it is preferable to use a photopolymerization initiator which reacts by light as an external stimulus. This makes it possible to obtain high bonding strength without damaging members to be laminated, without deforming the members due to strain generated between the members, or without generating cracks between the bonding material and the members.
As the light, suitable light such as ultraviolet light or visible light can be used, but light having a wavelength of 300nm or more and 420nm or less is preferably used.
The photopolymerization initiator may be one which is activated by light, and examples thereof include a radical photopolymerization initiator, a cationic photopolymerization initiator, and an anionic photopolymerization initiator, and for example, in the case of using a cationic photopolymerizable compound as the polymerizable compound, a cationic photopolymerization initiator is preferably used.
The photo cation polymerization initiator is not particularly limited as long as the ring-opening reaction of the cation polymerizable functional group can be initiated by light of the wavelength used, but it is preferable to use a compound which is initiated by light of a wavelength of 300 to 370nm and is inert in a wavelength region exceeding 370nm, and examples of such a compound include onium salts such as aromatic diazonium salts, aromatic iodonium salts, and aromatic sulfonium salts.
Specific examples of the onium salts include: optomer SP-150, Optomer SP-170, Optomer SP-171 (all manufactured by AdekA), UVE-1014 (general electronic), OMNICAT 250, OMNICAT270 (all manufactured by IGM Rein), IRGACURE 290 (manufactured by BASF), Sun SI-60L, Sun SI-80L, Sun SI-100L (all manufactured by Sanxin chemical industries), CPI-100P, CPI-101A, CPI-200K (all manufactured by San-Apro), and the like.
The photo cation polymerization initiator may be used alone, or two or more kinds thereof may be used in combination. Further, two-stage curing may be carried out by using a plurality of types of photo cation polymerization initiators having different effective active wavelengths.
The photo cation polymerization initiator may be used in combination with an anthracene-based sensitizer, a thioxanthone-based sensitizer, or the like, as required.
The compounding ratio of the photo cation polymerization initiator is preferably in the range of 0.001 to 30 parts by mass, more preferably in the range of 0.01 to 20 parts by mass, and still more preferably in the range of 0.1 to 10 parts by mass, relative to 100 parts by mass of the photo cation polymerization initiator. If the compounding ratio of the photo cation polymerization initiator is too small, curing required for the development of high bonding strength is insufficient, and if it is too large, curability is improved, but the time for which attachment is possible after irradiation with light may become too short.
The bonding material (X) is preferably an adhesive resin having a weight average molecular weight of 2000 to 2000000, in terms of excellent workability before curing and easy thickness adjustment. The weight average molecular weight is more preferably 5000 to 1000000, and still more preferably 5000 to 800000. If the weight average molecular weight is too small, the cohesive force of the joining material before curing becomes insufficient, and the joining material bleeds out over time, thereby deteriorating the workability. When the weight average molecular weight is too large, the compatibility with the polymerizable compound may be lowered.
Examples of the adhesive resin include polyester, polyurethane, and poly (meth) acrylate. These adhesive resins may be homopolymers or copolymers. These adhesive resins may be used alone or in combination of two or more.
The adhesive resin is preferably one having adhesiveness at room temperature because adhesiveness when the joining material is laminated on an adherend is improved. In order to impart adhesiveness to the adhesive resin, the glass transition temperature of the adhesive resin is preferably in the range of-40 ℃ to 20 ℃, more preferably in the range of-30 ℃ to 10 ℃. By setting the glass transition temperature within the above range, adhesiveness and a high elastic modulus can be imparted to the pressure-sensitive adhesive layer, and the bonding strength of the bonding material can be improved. The glass transition temperature of the adhesive resin can be calculated, for example, as a temperature at which a loss tangent (Tan δ) calculated by sandwiching a test piece between parallel disks serving as a measurement part of a dynamic viscoelasticity tester (trade name: ARES 2KSTD, manufactured by Rheometrics) and measuring a storage modulus (G') and a loss elastic modulus (G ") at a frequency of 1.0Hz reaches a maximum value.
Since the adhesive resin may be crosslinked, a functional group capable of reacting with a functional group contained in the crosslinking agent or the polymerizable compound may be introduced. Examples of the functional group include a hydroxyl group, a carboxyl group, an epoxy group, and an amino group, and it is preferably selected as appropriate within a range that does not inhibit polymerization of the polymerizable compound.
The adhesive resin is preferably used in a range of 5 to 900 parts by mass, preferably 10 to 700 parts by mass, and more preferably 20 to 400 parts by mass, based on 100 parts by mass of the curable resin. If the compounding ratio of the adhesive resin is too large, curing required for the development of high bonding strength becomes insufficient, and if it is too small, workability before curing is improved, but strength required for bonding may be reduced.
As described above, the bonding material (X) is preferably formed into an arbitrary shape such as a sheet shape in advance. In order to improve the work efficiency when the composition containing the polymerizable compound or the like is formed into a sheet or the like, it is preferable to use a composition containing a solvent in addition to the polymerizable compound or the polymerization initiator as the composition.
As the solvent, ester-based solvents such as methyl acetate, ethyl acetate, propyl acetate, and butyl acetate; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; aromatic hydrocarbon solvents such as toluene and xylene.
As the bonding material (X), a material containing another component may be used. Examples of the other component include fillers such as aluminum hydroxide, aluminum oxide, aluminum nitride, magnesium hydroxide, magnesium oxide, mica, talc, boron nitride, and glass flakes.
As the bonding material (X), for example, a material containing additives such as a filler, a softening agent, a stabilizer, an adhesion promoter, a leveling agent, an antifoaming agent, a plasticizer, a tackifier, fibers, an antioxidant, an ultraviolet absorber, an anti-hydrolysis agent, a thickener, a colorant such as a pigment, and a filler can be used within a range not impairing the effects of the present invention.
The bonding material (X) of the present invention can be produced by mixing the polymerizable compound with an optional component such as the polymerization initiator or the solvent.
When the components are mixed to produce the joining material (X), a dissolver, a Butterfly Mixer (Butterfly Mixer), a BDM twin-screw Mixer, a Planetary Mixer (Planetary Mixer), or the like may be used as necessary, and preferably, a dissolver and a Butterfly Mixer are used, and when the conductive filler is used, a Planetary Mixer is preferably used in terms of improving the dispersibility thereof.
The polymerization initiator is preferably used before curing the bonding material (X) or before forming the bonding material into a sheet.
The sheet-like bonding material can be produced, for example, by: after the composition containing the polymerizable compound and optional components such as the polymerization initiator and the solvent is produced, for example, the composition is applied to the surface of a release liner and dried.
The drying is preferably performed at a temperature of preferably about 40 to 120 ℃, more preferably about 50 to 90 ℃, in order to suppress the progress of the curing reaction of the sheet-like bonding material. In addition, foaming on the sheet surface due to rapid volatilization of the solvent or the like can be suppressed, and therefore, this is preferable.
The sheet-like bonding material may also be sandwiched by the release liner until use.
As the release liner, for example, paper such as kraft paper, cellophane paper, and high-quality paper; resin films such as polyethylene, polypropylene (oriented polypropylene (OPP), cast polypropylene (CPP)), polyethylene terephthalate, and the like; a laminated paper in which the paper and a resin film are laminated, a paper obtained by subjecting one or both sides of a paper obtained by filling the paper with clay, polyvinyl alcohol, or the like to a peeling treatment with a silicone resin or the like, or the like.
The laminate of the present invention is relatively flexible before curing, and therefore has excellent step following properties to an adherend, and becomes very hard after curing, and therefore can sufficiently join the adherend, and therefore can be used as a material for firmly joining various members used exclusively in an image display device to each other.
Examples of the image display device include components of a flat-panel image display device using an image display panel mounted with a Liquid Crystal Display (LCD), a Plasma Display (PDP), an Electroluminescence (EL), an organic EL, a micro LED, a Quantum Dot (QD), or the like, such as a Personal computer, a mobile phone, a smartphone, a tablet Personal computer, or a mobile terminal (Personal Digital Assistant (PDA)), a game machine, a Television (TV), a car navigation system, a touch panel, and a Digital graphic tablet. Examples of the constituent members include an image display panel, a circuit board, a back cover, a frame, and a chassis.
Examples
Hereinafter, examples and comparative examples will be specifically described.
< preparation of acrylic copolymer (1) >
In a reaction vessel equipped with a stirrer for producing an acrylic copolymer, a condenser-cooler, a thermometer, a dropping funnel and a nitrogen inlet, 25 parts by mass of n-butyl acrylate, 80 parts by mass of 2-methoxyethyl acrylate, 1 part by mass of 2-hydroxyethyl acrylate and 0.2 part by mass of 2,2' -azobisisobutyronitrile as a polymerization initiator were dissolved in 100 parts by mass of ethyl acetate, and after nitrogen substitution, polymerization was carried out at 80 ℃ for 8 hours to obtain an acrylic copolymer (1) having a solid content of 50 mass% and a weight average molecular weight of 75 ten thousand. The glass transition temperature was-25 ℃.
< preparation of polyurethane (1) >
50 parts by mass of an aliphatic polycarbonate polyol having a number average molecular weight of 2000 obtained by reacting 1, 5-pentanediol, 1, 6-hexanediol, and a dialkyl carbonate and 30 parts by mass of a polyester polyol having a number average molecular weight of 4500 obtained by reacting 1, 6-hexanediol and adipic acid were mixed in a reaction vessel, and the mixture was heated to 100 ℃ under reduced pressure, thereby dehydrating the mixture until the water content became 0.05 mass%.
Next, a mixture of the aliphatic polycarbonate polyol and the polyester polyol was cooled to 70 ℃ and then mixed with 14.5 parts by mass of dicyclohexylmethane-4, 4' -diisocyanate, and then the mixture was heated to 100 ℃ to react for 3 hours. Thereafter, the methyl ethyl ketone was adjusted so that the solid content became 50 mass%, thereby obtaining a polyurethane (1). The glass transition temperature was-28 ℃.
< preparation of bonding Material (A-1) >
50 parts by mass of EX-321L (tradename.
Next, the adhesive resin coating (a-1) was applied to the surface of a release liner (a liner obtained by peeling one surface of a polyethylene terephthalate film having a thickness of 75 μm with a silicone compound) using a bar-shaped metal applicator so that the dried thickness became 100 μm.
Further, the coating was dried by being thrown into a dryer at 85 ℃ for 5 minutes, and a release liner (a liner obtained by peeling one surface of a polyethylene terephthalate film having a thickness of 38 μm from a silicone compound) was attached to one surface of the dried coating. Thereafter, the resultant was aged at 40 ℃ for 72 hours to obtain a sheet-like bonding material (A-1) having a thickness of 100 μm.
Since the bonding material (a-1) has a photopolymerization initiator and an epoxy group as a reaction site, the curing reaction of the epoxy group can be activated by irradiation with light.
The bonding material (A-1) had a storage modulus at 23 ℃ of 1.7X 104Pa, storage modulus at 70 ℃ of 2.9X 103Pa。
The storage modulus at 23 ℃ and 70 ℃ of the bonding material (A-1) was calculated by sandwiching a test piece between parallel disks serving as a measurement part of the same testing machine using a dynamic viscoelasticity testing machine (product name: Alis (ARES)2KSTD, manufactured by Rheometrics), and measuring the storage modulus at a temperature rise rate of 3 ℃/min, a measurement frequency of 1.0Hz, and a measurement temperature range of 0 ℃ to 200 ℃. As the test piece used for the measurement, a test piece obtained by removing the release liner on one surface of the bonding material (a-1), stacking the test piece so that the thickness thereof becomes 1mm, and cutting the test piece into a circular shape having a size of 8mm in diameter was used.
< preparation of bonding Material (A-2) >
The adhesive resin coating material (a-2) and the adhesive material (a-2) were obtained by the same method as the preparation of the adhesive material (a-1) except that 50 parts by mass of CEL-2021P (alicyclic epoxy resin, manufactured by Daicel corporation) was used instead of EX-321L (trihydroxymethyl propane polyglycidyl ether type epoxy resin, manufactured by Nagaseschemitex).
Since the bonding material (a-2) has a photopolymerization initiator and also has an epoxy group as a reaction site, the curing reaction of the epoxy group can be activated by irradiation with light.
The bonding material (A-2) had a storage modulus at 23 ℃ of 9.3X 103Pa, storage modulus at 70 ℃ of 1.0X 103Pa。
< preparation of bonding Material (A-3) >
The adhesive resin paint (a-3) and the adhesive material (A-3) were obtained in the same manner as in the preparation of the adhesive material (A-1) except that 2.0 parts by mass of DICY-7 (dicyandiamide, manufactured by Mitsubishi chemical) was used in place of the CPI-100P.
Since the bonding material (a-3) has a thermal polymerization initiator and an epoxy group as a reaction site, the curing reaction of the epoxy group can be activated by heating.
The bonding material (A-3) had a storage modulus at 23 ℃ of 9.6X 103Pa, storage modulus at 70 ℃ of 1.0X 103Pa。
As the adherend used in the present example and comparative example, an aluminum plate having a smooth surface and a thickness of 0.05mm was cut into a width of 15mm × a length of 150mm, and this was used as the adherend (I). An epoxy glass plate having a smooth surface and a thickness of 1.0mm (KEL-GEF, manufactured by Xinshenhu electric machine Co., Ltd.) was cut into a width of 15mm × a length of 150mm, and the cut product was used as an adherend (II). The adherend (I) and the adherend (II) are opaque materials.
< preparation of bonding Material (A-4) >
The adhesive resin coating material (a-4) and the adhesive material (a-4) were obtained in the same manner as in the preparation of the adhesive material (a-1) except that 100 parts by mass of the polyurethane (1) was used instead of the acrylic copolymer (1), the amount of CEL-2021P (cellosolve (Daicel) and alicyclic epoxy resin) was changed from 50 parts by mass to 21 parts by mass, the amount of CPI-100P (manufactured by thomson (San-Apro) and sulfonium salt and solid content concentration was 50%) was changed from 2 parts by mass to 2.9 parts by mass, and the amount of Bernouk (BURNOCK) DN980 (manufactured by DIC and hexamethylene diisocyanate type isocyanate crosslinking agent) was changed from 0.20 parts by mass to 0 parts by mass.
Since the bonding material (a-4) has a photopolymerization initiator and also has an epoxy group as a reaction site, the curing reaction of the epoxy group can be activated by irradiation with light.
The bonding material (A-4) had a storage modulus at 25 ℃ of 4.9X 104Pa, storage modulus at 70 ℃ of 1.2X 101Pa。
(example 1)
A sample obtained by cutting the joining material (A-1) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed and attached to the adherend (I) at 23 ℃.
The sample was left standing at 70 ℃ for 30 minutes in a state of being loaded with 1kg from the adherend.
After the placement, the 1kg load was released from the patch, and the patch was left to stand at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the exposed surface layer of the joining material was irradiated with 250mJ/cm using an electrodeless lamp (fusion lamp H valve)2Ultraviolet rays of (1).
After the irradiation, the sheet was left at 23 ℃ for 2 minutes, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded using a hot press apparatus heated to 40 ℃ for 10 seconds in a state of being pressurized at 0.5 MPa.
The laminate after press-bonding was left to stand at 70 ℃ for 1 hour under heating, left to stand at 23 ℃ for 30 minutes under cooling, and the obtained sample was designated as an evaluation sample (X-1).
The time required for the preparation of the evaluation sample (X-1) was 2 hours, 32 minutes and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X-1) was 1 hour.
The shear adhesion of the evaluation sample (X-1) was determined by performing a tensile test in the 180 degree direction at a tensile rate of 10 mm/min using a tensile testing machine with the ends of the adherend (I) and the adherend (II) held between the evaluation sample (X-1). The shear adhesion of the evaluation sample (X-1) at this time was 920 Pa.
Further, the cured product (B-1) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X-1) had a storage modulus at 25 ℃ of 5.7X 105Pa。
The storage modulus at 25 ℃ of the cured product (B-1) of the sheet-like bonding material (A-1) was measured using a dynamic viscoelasticity measuring apparatus (RSA III, manufactured by TA Instruments) at a temperature rise rate of 3 ℃/min, a measurement frequency of 1.0Hz, and a measurement temperature range of 0 to 200 ℃, and the storage modulus (G') at 25 ℃ and 100 ℃ were calculated, respectively.
(example 2)
A sample obtained by cutting the joining material (A-1) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed and attached to the adherend (I) at 23 ℃.
The sticker was left to stand in an environment at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the exposed surface layer of the joining material was irradiated with 250mJ/cm using an electrodeless lamp (fusion lamp H valve)2Ultraviolet rays of (1).
After the irradiation, the sheet was left at 23 ℃ for 2 minutes, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded for 10 seconds in a state of being pressurized at 0.5MPa using a hot press apparatus heated to 40 ℃.
The laminate after press-bonding was left to stand at 70 ℃ for 1 hour under heating, left to stand at 23 ℃ for 30 minutes under cooling, and the obtained sample was designated as an evaluation sample (X-2).
The time required for the preparation of the evaluation sample (X-2) was 2 hours, 2 minutes and 10 seconds. In addition, the time required for curing the evaluation sample (X-2) was 1 hour.
The shear adhesion of the evaluation sample (X-2) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X-2) at this time was 880 Pa.
The cured product (B-2) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X-2) had a storage modulus at 25 ℃ of 4.9X 105Pa。
(example 3)
An evaluation sample (X-3) was produced in the same manner as in example 1, except that the bonding material (a-2) was used.
The time required for the preparation of the evaluation sample (X-3) was 2 hours, 32 minutes and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X-3) was 1 hour.
The shear adhesion of the evaluation sample (X-3) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X-3) at this time was 1100 Pa.
The cured product (B-3) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X-3) had a storage modulus at 25 ℃ of 6.3X 106Pa。
(example 4)
Except that the joining material (A-4) was used, and the ultraviolet ray irradiation amount using an electrodeless lamp (fusion lamp H valve) was from 250mJ/cm2Changed to 500mJ/cm2Except for this, an evaluation sample (X-4) was prepared in the same manner as in example 1.
The time required for the preparation of the evaluation sample (X-4) was 2 hours, 32 minutes and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X-4) was 1 hour.
The shear adhesion of the evaluation sample (X-4) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X-4) at this time was 3700 Pa.
The cured product (B-4) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X-4) had a storage modulus at 25 ℃ of 5.8X 108Pa。
(example 5)
A sample obtained by cutting the joining material (A-4) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed and attached to the adherend (I) at 23 ℃.
Thereafter, the sticker was left to stand in an environment at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the exposed surface layer of the joining material was irradiated with 500mJ/cm using an electrodeless lamp (fusion lamp H valve)2Ultraviolet rays of (1).
After the irradiation, the sheet was left at 23 ℃ for 2 minutes, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded for 10 seconds in a state of being pressurized at 0.5MPa using a hot press apparatus heated to 40 ℃.
Thereafter, the sample was allowed to stand at 70 ℃ for 5 minutes in a state of being loaded with 1kg from the adherend.
After the placement, the 1kg load was released from the patch, and the patch was heated and placed at 70 ℃ for 55 minutes, placed at 23 ℃ for 30 minutes, and cooled, and the obtained sample was set as an evaluation sample (X-5).
The time required for the preparation of the evaluation sample (X-5) was 2 hours, 2 minutes and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X-5) was 1 hour.
The shear adhesion of the evaluation sample (X-4) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X-4) at this time was 3500 Pa.
The cured product (B-4) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X-4) had a storage modulus at 25 ℃ of 4.3X 108Pa。
Comparative example 1
A sample obtained by cutting the joining material (A-1) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed, and the adherend (I) was attached.
The sample was left standing at 70 ℃ for 30 minutes in a state of being loaded with 1kg from the adherend.
After the placement, the 1kg load was released from the patch, and the patch was left to stand at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded using a hot press apparatus heated to 40 ℃ for 10 seconds in a state of being pressed at 0.5 MPa.
After the pressure bonding, the adherend (I) side to be attached was irradiated with 250mJ/cm using an electrodeless lamp (fusion lamp H valve)2Ultraviolet rays of (1).
The irradiated laminate was left to stand at 70 ℃ for 1 hour under heating, left to stand at 23 ℃ for 30 minutes under cooling, and the obtained sample was designated as an evaluation sample (X' -1).
The time required for the preparation of the evaluation sample (X' -1) was 2 hours, 30 minutes and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X' -1) was 1 hour.
The shear adhesion of the evaluation sample (X' -1) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X' -1) at this time was 40 Pa.
Further, the cured product (B '-1) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X' -1) had a storage modulus at 25 ℃ of 1.7X 104Pa。
Comparative example 2
A sample obtained by cutting the joining material (A-1) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed, and the adherend (I) was attached.
The sticker was left to stand in an environment at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded using a hot press apparatus heated to 40 ℃ for 10 seconds in a state of being pressed at 0.5 MPa.
After the pressure bonding, the adherend (II) side to be attached was irradiated with 250mJ/cm using an electrodeless lamp (fusion lamp H valve)2Ultraviolet rays of (1).
The irradiated laminate was left to stand at 70 ℃ for 1 hour under heating, left to stand at 23 ℃ for 30 minutes under cooling, and the obtained sample was designated as an evaluation sample (X' -2).
The time required for the preparation of the evaluation sample (X' -2) was 2 hours and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X' -2) was 1 hour.
The shear adhesion of the evaluation sample (X' -2) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X' -2) at this time was 38 Pa.
Further, the cured product (B '-2) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X' -2) had a storage modulus at 25 ℃ of 1.7X 104Pa。
Comparative example 3
A sample obtained by cutting the joining material (A-3) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed, and the adherend (I) was attached.
The sample was left standing at 70 ℃ for 30 minutes in a state of being loaded with 1kg from the adherend.
After the placement, the 1kg load was released from the patch, and the patch was left to stand at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded using a hot press apparatus heated to 40 ℃ for 10 seconds in a state of being pressed at 0.5 MPa.
The pressurized laminate was left to stand at 180 ℃ for 1 hour under heating, left to stand at 23 ℃ for 30 minutes under cooling, and the obtained sample was designated as an evaluation sample (X' -3).
The total time required for the preparation of the evaluation sample (X' -3) was 2 hours, 30 minutes and 10 seconds. In addition, the time required for the evaluation of curing of the sample (X' -3) was 1 hour. The evaluation sample (X' -3) was visually confirmed, and as a result, the adherend (II) was deteriorated and discolored to yellow.
The shear adhesion of the evaluation sample (X' -3) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X' -3) at this time was 203 Pa.
Further, the cured product (B '-3) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X' -3) had a storage modulus at 25 ℃ of 7.5X 106Pa。
Comparative example 4
A sample obtained by cutting the joining material (A-3) into a size of 10mm in width × 10mm in length was set as a test sample. One release liner of the test sample was removed, and the adherend (I) was attached.
The sample was left standing at 70 ℃ for 30 minutes in a state of being loaded with 1kg from the adherend.
After the placement, the 1kg load was released from the patch, and the patch was left to stand at 23 ℃ for 30 minutes. Thereafter, the release liner was removed from the other surface of the test sample, and the adherend (II) was attached to the surface of the irradiated bonding material layer, and press-bonded using a hot press apparatus heated to 40 ℃ for 10 seconds in a state of being pressed at 0.5 MPa.
The pressurized laminate was left to stand at 70 ℃ for 3 hours under heating, and was left to stand at 23 ℃ for 30 minutes under cooling, and the obtained sample was designated as an evaluation sample (X' -4).
The time required for the preparation of the evaluation sample (X' -4) was 4 hours, 30 minutes and 10 seconds. In addition, the time required for curing the evaluation sample (X' -4) was 3 hours.
The shear adhesion of the evaluation sample (X' -4) was determined in the same manner as in example 1. The shear adhesion of the evaluation sample (X' -4) at this time was 115 Pa.
Further, the cured product (B '-3) of the sheet-like bonding material (A-1) obtained by the same curing method as that for the evaluation sample (X' -3) had a storage modulus at 25 ℃ of 6.5X 104Pa。
[ Table 1]
[ Table 2]
From the results, it is understood that in examples 1 to 5, laminates can be produced in a short time and at a low temperature, and sufficient bonding can be obtained even for an opaque adherend. On the other hand, in comparative examples 1 to 2, although the laminate was produced in a short time and at a low temperature, the bonding material was not cured, and sufficient bonding could not be obtained. In comparative example 3, although the joining could be achieved in a short time, the adherend was observed to deteriorate because high temperature was required for curing. In comparative example 4, bonding could be achieved at a low temperature, but a large amount of time was required.
Claims (13)
1. A method for producing a laminate comprising an adherend (C1) and a bonding material (X), the method comprising, in this order:
a step [1] of activating a reaction site of the bonding material (X);
a step [2] of attaching the bonding material (X) to an adherend (C1); and
and (3) curing the bonding material (X).
2. A method for producing a laminate comprising an adherend (C1) and an adherend (C2) with a bonding material (X) therebetween, said method comprising the steps of:
a step [01] of attaching the bonding material (X) to an adherend (C2);
a step [1] of activating a reaction site of the bonding material (X);
a step [2] of attaching the bonding material (X) to an adherend (C1); and
a step [3] of curing the bonding material (X),
at least one of the steps [01] and [1] and [2] and [3] includes a curing step [02] which is a step of performing step following.
3. The manufacturing method according to claim 2, wherein the step [02] includes a step of heating.
4. The production method according to claim 2 or 3, wherein at least one of the step [2] and the step [01] includes a step of heating.
5. The production method according to any one of claims 1 to 4, wherein the step [3] includes a step of heating.
6. The production method according to any one of claims 2 to 5, wherein at least one of the steps [01], [02], [2] and [3] includes a step of heating at 150 ℃ or lower.
7. The production method according to any one of claims 1 to 6, wherein light is used as a method for activating the reaction site of the bonding material (X) in the step [1 ].
8. The production method according to any one of claims 2 to 7, wherein in the step [01]]In (2), the storage modulus of the bonding material (X) at the time of bonding is 5.0X 103Pa is above; in the step [02]]The storage modulus of the bonding material (X) at the time of the step-up/step-down tracking is less than 5.0X 103Pa。
9. The production method according to any one of claims 1 to 8, wherein the step [3]]The storage modulus of the subsequent bonding material (X) at 25 ℃ was 1.0X 105Pa or above.
10. The manufacturing method according to any one of claims 1 to 9, wherein the joining material (X) is in a sheet form.
11. The production method according to any one of claims 1 to 10, wherein the bonding material (X) comprises (1) at least one resin having cationic polymerizability, (2) a resin having a weight average molecular weight of 2000 to 2000000, and (3) a resin composition containing a photoacid generator and/or a thermal acid generator.
12. The production method according to claim 11, wherein the cationically polymerizable resin has an epoxy group as a reaction site.
13. The manufacturing method according to any one of claims 1 to 12, wherein the laminate is used for an image display device.
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| PCT/JP2018/033955 WO2019065268A1 (en) | 2017-09-27 | 2018-09-13 | Method for producing layered product including curable joining material |
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| JP2001134736A (en) * | 1999-11-09 | 2001-05-18 | Sekisui Chem Co Ltd | Ic card and producing method therefor |
| JP2002536490A (en) * | 1999-02-05 | 2002-10-29 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | Pressure sensitive adhesive tape |
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| CN106104658A (en) * | 2014-03-10 | 2016-11-09 | 三菱树脂株式会社 | The manufacture method of image display device composition duplexer |
| CN107207914A (en) * | 2015-01-21 | 2017-09-26 | 株式会社寺冈制作所 | The manufacture method of the optical component of adhesive sheet and its manufacture method and the use adhesive sheet |
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| JP2011184582A (en) * | 2010-03-09 | 2011-09-22 | Three M Innovative Properties Co | Adhesive sheet for optical use |
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| JP2002536490A (en) * | 1999-02-05 | 2002-10-29 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | Pressure sensitive adhesive tape |
| JP2001134736A (en) * | 1999-11-09 | 2001-05-18 | Sekisui Chem Co Ltd | Ic card and producing method therefor |
| CN1381756A (en) * | 2001-04-16 | 2002-11-27 | 夏普公司 | Adhesive sheet, layered sheet and liquid crystal display unit |
| CN104937059A (en) * | 2013-02-12 | 2015-09-23 | 三菱树脂株式会社 | Transparent double-sided adhesive sheet, laminate obtained using same for constituting image display device, process for producing said laminate, and image display device obtained using said laminate |
| CN106104658A (en) * | 2014-03-10 | 2016-11-09 | 三菱树脂株式会社 | The manufacture method of image display device composition duplexer |
| CN107207914A (en) * | 2015-01-21 | 2017-09-26 | 株式会社寺冈制作所 | The manufacture method of the optical component of adhesive sheet and its manufacture method and the use adhesive sheet |
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| JP6798622B2 (en) | 2020-12-09 |
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