JP7111041B2 - Laminate manufacturing method - Google Patents

Description

TECHNICAL FIELD The present invention relates to a method for producing a laminate, and more particularly to a method for producing a laminate having an adhesive layer made of a cured product of a photocurable silicone composition.

Electronic devices with image display capabilities such as displays and touch panels generally consist of a protective cover panel with excellent light transmittance made of highly transparent resin such as acrylic or polycarbonate or glass, as well as a polarizing plate and an image display element. It has an image display section provided on the substrate.
An optically transparent resin layer is often arranged between the cover panel and the image display section in order to improve visibility and mechanical strength.

As the optically transparent resin layer, an ultraviolet addition-curable transparent silicone adhesive composition has been proposed (Patent Document 1). In this adhesive composition, since the curing reaction by the platinum catalyst gradually progresses when irradiated with ultraviolet rays, the adhesive composition is applied on the polarizing plate of the image display portion, and after ultraviolet irradiation, the cover panel is attached. Machining processes can be employed. As a result, it is possible to use it in places (dark areas) that are not exposed to UV rays using the integrated molding method described above, and it is also possible to use cover panels with UV absorbers to provide weather resistance. is obtained.

On the other hand, when the polarizing plate and the liquid resin are in contact with each other, when the liquid resin is irradiated with ultraviolet rays having a peak wavelength of 365 nm, which is generally used for ultraviolet curing, a phenomenon occurs in which curing of the resin is delayed. This phenomenon is considered to be caused by the curing inhibitor generated from the polarizing plate by the irradiation of ultraviolet rays, which inhibits the activity of the platinum catalyst. When this phenomenon occurs, the curing of the resin on the polarizing plate becomes insufficient, and as a result, the adhesion and adhesive strength are lowered, and the reliability of the device is impaired.
In such cases, it becomes necessary to add a heating process using heating equipment or to extend the standing time until curing in order to ensure curability. There is a concern that warping of members and deterioration of resin due to expansion and contraction due to deformation are likely to occur. Moreover, since the curing behavior varies depending on the type of polarizing plate, there is also the problem that the manufacturing process must be reviewed each time the polarizing plate is changed.

JP 2015-110752 A

The present invention has been made in view of the above circumstances, and even when an adhesive layer made of a photocurable silicone composition is cured at room temperature, it is not inhibited by an adherend such as a polarizing plate. It aims at providing the manufacturing method of a laminated body.

As a result of intensive studies to solve the above problems, the present inventors have found that a silicone composition containing a predetermined organopolysiloxane is cured by irradiating it with light of a specific wavelength to form an adhesive layer at room temperature. The inventors have found that the adhesive layer can be rapidly cured on the polarizing plate even when the curing is performed with , and completed the present invention.

That is, the present invention
1. A method for producing a laminate comprising a first substrate and an adhesive layer laminated on the first substrate, wherein the adhesive layer contains the following components (A) to (C) A method for producing a laminate comprising irradiating a photocurable silicone composition with light having a peak wavelength of 380 to 420 nm to cure the composition,
(A) Linear organopolysiloxane represented by the following average formula ( ¹ ): 100 parts by mass (R1R22SiO1 _/2 ⁾ _a ( _{R23SiO1 /2 )} ² _{- a} (Ar2 _SiO2 / ² ) _b ( _{R22SiO2 /2} ) _c (1)
{wherein each R ¹ independently represents a substituted or unsubstituted alkenyl group, each R ² independently represents a substituted or unsubstituted alkyl group, and each Ar independently represents represents a substituted or unsubstituted aryl group, a represents a number of 0.3 to 2, b is 0 to 100, c is 1 to 1,000, and b / (b + c) = 0 to 0 Represents a number that satisfies .7. }
(B) Organohydrogenpolysiloxane having at least two Si—H bonds in one molecule, represented by the following average compositional formula (2): 1 to 200 parts by mass R ³ _d H _e SiO _{[(4- de)/2]} (2)
(wherein each R ³ independently represents a substituted or unsubstituted monovalent hydrocarbon group excluding an aliphatic unsaturated hydrocarbon group; d and e are 0.7≤d≤2.5; represents a number that satisfies 0.01≦e≦1.0 and 0.8≦d+e≦2.7.)
(C) a platinum compound 2 having at least one of a β-diketonato group, a β-ketoesterate group, and a 1,3-diesterate group as a ligand, wherein the component (C) is bisacetylacetonatoplatinum (II) ), the manufacturing method of the laminate of 1,
3. (i) a coating step of coating the photocurable silicone composition on the surface of the first substrate;
(ii) a light irradiation step of irradiating the photocurable silicone composition with light having a peak wavelength of 380 to 420 nm;
(iii) a curing step of curing the photocurable silicone composition to form an adhesive layer;
(iv) Lamination in which a second substrate is laminated on a photocurable silicone composition or adhesive layer and the first and second substrates are laminated via the adhesive composition or adhesive layer. 1 or 2 methods of manufacturing a laminate,
4. The method for producing a laminate of 3, wherein the curing step is performed at 5 to 35 ° C.
5. The method for producing a laminate of 3 or 4, wherein the second substrate is a polarizing plate or a polarizing film;
6. The method for producing a laminate according to any one of 1 to 5, wherein the first substrate is a polarizing plate or a polarizing film;
7. The method for producing a laminate according to any one of 1 to 6, wherein the peak wavelength of the light is 405 nm;
8. Provided is the method for producing a laminate according to any one of 1 to 7, wherein the laminate is an image display device.

According to the method for producing a laminate of the present invention, the photocurable silicone composition cures rapidly even at a room temperature of about 25° C. regardless of the type of polarizing plate with which it comes into contact. The manufacturing method of the present invention having such characteristics can be suitably used as a bonding method for image display devices such as touch panels and displays.

The present invention will be specifically described below.
A method for producing a laminate according to the present invention is a method for producing a laminate including a first base material and an adhesive layer laminated on the first base material, wherein the adhesive layer is the above ( It is formed by irradiating a photocurable silicone composition containing components A) to (C) with light having a peak wavelength of 380 to 420 nm for curing.

[Photocurable silicone adhesive composition]
Each component constituting the photocurable silicone adhesive composition used in the present invention will be described.
[1] Component (A) Component (A) in the photocurable silicone composition used in the present invention is a linear organopolysiloxane represented by the following average formula (1).
(R1R22SiO1 _/2 ⁾ _a (R23SiO1 _/2 ⁾ _{2 -a} ( _Ar2SiO2 / ² ) _{b ( R22SiO2 /2 ) c} ( ¹ )

In formula (1), each R ¹ independently represents a substituted or unsubstituted alkenyl group.
This alkenyl group is not particularly limited and may be linear, branched or cyclic, but preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Those of numbers 2 to 6 are even more preferable.
Specific examples of alkenyl groups include vinyl, allyl, butenyl, pentenyl, and hexenyl groups, with vinyl groups being preferred.
Also, some or all of the hydrogen atoms in the alkenyl group may be substituted with halogen atoms such as F, Cl, and Br, cyano groups, and the like.

Each R ² independently represents a substituted or unsubstituted alkyl group.
The alkyl group is not particularly limited and may be linear, branched or cyclic, preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, Numbers 1 to 5 are even more preferred.
Specific examples of alkyl groups include linear or branched alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, n-hexyl and n-heptyl groups; A cyclic alkyl group and the like can be mentioned.
Further, some or all of the hydrogen atoms in the above alkyl groups may be substituted with halogen atoms such as F, Cl, and Br, cyano groups, etc. Specific examples of such groups include chloromethyl, 3 -chloropropyl, and halogen-substituted alkyl groups such as 3,3,3-trifluoropropyl groups.
Among these, a methyl group is preferable from the viewpoint of heat resistance.

Each Ar independently represents a substituted or unsubstituted aryl group.
The aryl group is not particularly limited, but preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms.
Specific examples of aryl groups include phenyl, naphthyl, tolyl, xylyl, and mesityl groups.
In addition, some or all of the hydrogen atoms in the aryl group may be substituted with a halogen atom such as F, Cl, Br, or a cyano group. mentioned.
Among these, a phenyl group is preferred.

In the above formula (1), a represents a number from 0.3 to 2. If a is less than 0.3, the content of R ¹ is low, so that the uncrosslinked component may bleed out or the composition may become too soft.
b is a number from 0 to 100, preferably a number from 0 to 50; If b is greater than 100, the viscosity may become too high.
c is a number from 1 to 1,000, preferably from 1 to 500, more preferably from 100 to 300. When c is less than 1, the cured product may become too hard, and when it is greater than 1,000, the viscosity may become too high.
b/(b+c) is 0 to 0.7, preferably 0 to 0.3. If b/(b+c) is greater than 0.7, the viscosity may become too high.

The molecular weight of component (A) is preferably 500 to 100,000, preferably 700 to 50,000, in terms of standard polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) using THF solvent. More preferably, 1,000 to 30,000 is even more preferable.

Specific examples of component (A) include, but are not limited to, those represented by the following average formulas (3) to (5).
The organopolysiloxane of component (A) may be used alone or in combination of two or more.

〔式中、Ｍｅは、メチル基を表し、Ｐｈは、フェニル基を表し、Ｖｉは、ビニル基を表す（以下同様）。式（３）において、シロキサン単位の配列順は任意である。〕

[In the formula, Me represents a methyl group, Ph represents a phenyl group, and Vi represents a vinyl group (the same applies hereinafter). In formula (3), the order of arrangement of the siloxane units is arbitrary. ]

[2] Component (B) Component (B) in the photocurable silicone composition used in the present invention has at least two Si—H bonds in one molecule, represented by the following average compositional formula (2). It is an organohydrogenpolysiloxane.
^R3dHeSiO _{[ ( 4-de)/2]} (2)

In formula (2), each R ³ independently represents a substituted or unsubstituted monovalent hydrocarbon group other than an aliphatic unsaturated hydrocarbon group.
The monovalent hydrocarbon group for R ³ is not particularly limited as long as it does not have an aliphatic unsaturated hydrocarbon group, and may be linear, branched or cyclic, but it should have 1 to 20 carbon atoms. Preferably, those having 1 to 10 carbon atoms are more preferred, and those having 1 to 5 carbon atoms are even more preferred.
Specific examples thereof include linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl and n-hexyl groups; cyclic alkyl groups such as cyclohexyl groups; phenyl and tolyl groups. aryl groups such as benzyl; and aralkyl groups such as benzyl and phenylethyl groups.
Further, some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with halogen atoms such as F, Cl, and Br, cyano groups, etc. Specific examples of such groups include Halogen-substituted hydrocarbon groups such as 3,3,3-trifluoropropyl group; cyano-substituted hydrocarbon groups such as 2-cyanoethyl group;
Among these, a methyl group is preferred.

From the viewpoint of compatibility with component (A) and the physical properties of the cured product, 20 mol % or more of the total number of R ³ and Si—H groups in component (B) is preferably a methyl group. A methyl group is more preferable for mol % or more.

In formula (2), d is a number of 0.7 ≤ d ≤ 2.5, preferably a number of 0.7 ≤ d ≤ 2.1, and a number of 1.0 ≤ d ≤ 1.8 more preferred. If d is less than 0.7, there is a risk of foaming during curing, and the change in hardness over time tends to increase. If d exceeds 2.5, sufficient hardness cannot be obtained.
e is a number satisfying 0.01≦e≦1.0, preferably a number satisfying 0.02≦e≦1.0, and more preferably a number satisfying 0.1≦e≦1.0. If e is less than 0.01, sufficient hardness cannot be obtained, and if it exceeds 1.0, there is a risk of foaming during curing, and the change in hardness over time tends to increase.
d+e satisfies 0.8≦d+e≦2.7, preferably 1≦d+e≦2.4, more preferably 1.6≦d+e≦2.2. When d+e is less than 0.8, the cured product tends to be hard and brittle, and cracks tend to occur in the adhesive layer.

The kinematic viscosity of component (B) organohydrogenpolysiloxane at 25° C. is preferably 1,000 mm ² /s or less, more preferably 0.5 to 1,000 mPa·s, and more preferably 1 to 500 mm ² /s. More preferred. In the present invention, kinematic viscosity is a value measured using a Canon Fenske viscometer.

The amount of the organohydrogenpolysiloxane of component (B) is 1 to 200 parts by mass, preferably 5 to 80 parts by mass, per 100 parts by mass of component (A). If the amount is less than 1 part by mass, curability will be insufficient, and if it exceeds 200 parts by mass, sufficient hardness and strength will not be obtained.
The organohydrogenpolysiloxane of component (B) has a molar ratio of silicon-bonded hydrogen atoms (that is, SiH groups) in component (B) to alkenyl groups in component (A) of 0.5 to 2. It is preferably blended in an amount of mol/mol, and more preferably blended in an amount of 1 to 1.5 mol/mol.

Specific examples of component (B) include, but are not limited to, those represented by the following average formulas (6) to (8).
The organohydrogenpolysiloxane of component (B) may be used alone or in combination of two or more.
_Me2.0H0.1SiO [ _{1.9 /2]} (6)
_Me1.8H0.3SiO [ _{1.9 /2]} (7)
_Me1.7H0.4SiO [ _{1.9 /2]} (8)

[3] Component (C) The component (C) in the photocurable silicone composition used in the present invention coordinates at least one of a β-diketonate group, a β-ketoesterate group, and a 1,3-diesterate group. It is a platinum compound that has as a child. This platinum compound is inactive when shielded from light, but changes to an active platinum catalyst at room temperature by irradiation with light having a wavelength of 380 to 420 nm, and the alkenyl group in the component (A) described above and ( B) It has a function of promoting hydrosilylation reaction with silicon-bonded hydrogen atoms in the component.

Specific examples of component (C) include trimethyl(acetylacetonato)platinum complex, trimethyl(2,4-pentanedionate)platinum complex, trimethyl(3,5-heptanedionate)platinum complex, trimethyl(methylacetoacetate) ) platinum complex, bis(acetylacetonato)platinum complex, bis(2,4-pentanedionato)platinum complex, bis(2,4-hexanedionato)platinum complex, bis(2,4-heptanedionato)platinum complex, bis(3,5-heptanedionato)platinum complex, bis(1-phenyl-1,3-butanedionato)platinum complex, bis(1,3-diphenyl-1,3-propanedionato)platinum complex, etc., and these may be used singly or in combination of two or more.
Among these, bis(acetylacetonato)platinum complexes and their derivatives modified on the acetylacetonato group are preferred.

The content of component (C) is not limited as long as it promotes curing (hydrosilylation reaction) of the photocurable silicone composition. is preferably in the range of 0.01 to 500 ppm, more preferably in the range of 0.05 to 100 ppm, and even more preferably in the range of 0.01 to 50 ppm.

[4] Component (D) In the photocurable silicone composition used in the present invention, the component (D) may optionally be added to provide adhesiveness to a substrate such as a polarizing plate, glass, polycarbonate resin or acrylic resin. Adhesion aids for application may be added.
Among component (D), specific examples of adhesion promoters containing siloxane bonds include vinyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-1003), γ-(glycidyloxypropyl)trimethoxysilane ( Shin-Etsu Chemical Co., Ltd., KBM-403), γ-(methacryloxypropyl)trimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-503), hydrolysates thereof, and represented by the following structural formula and the like.

Further, specific examples of adhesion promoters that do not contain siloxane bonds include allyl glycidyl ether, vinylcyclohexene monoxide, diethyl 2-allylmalonate, diallyl bisphenol ether, allyl benzoate, diallyl phthalate, tetraallyl pyromellitic acid ester ( Fuji Film Wako Pure Chemical Industries, Ltd., TRIAM805), triallyl isocyanurate, and the like.
In addition, (D) component may be used individually by 1 type, or may be used in combination of 2 or more type.

When component (D) is used, the amount added is preferably 0.05 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, per 100 parts by mass of component (A). If the blending amount of the component (D) is within the above range, appropriate adhesiveness can be imparted.

[5] Component (E) The photocurable silicone adhesive composition used in the present invention may be thickened or gelled prior to heat curing, such as when the composition is prepared or when the composition is applied to a substrate. For the purpose of controlling the reactivity of the hydrosilylation reaction catalyst so as not to cause reaction, (E) a reaction control agent may be added as necessary.
Specific examples of reaction control agents include 3-methyl-1-butyn-3-ol, 3-methyl-1-pentyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 1-ethynyl cyclohexanol, ethynylmethyldecylcarbinol, 3-methyl-3-trimethylsiloxy-1-butyne, 3-methyl-3-trimethylsiloxy-1-pentyne, 3,5-dimethyl-3-trimethylsiloxy-1-hexyne, 1-ethynyl-1-trimethylsiloxycyclohexane, bis(2,2-dimethyl-3-butynoxy)dimethylsilane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, 1,1,3,3-tetramethyl-1,3-divinyldisiloxane and the like can be mentioned, and these may be used alone or in combination of two or more.
Among these, 1-ethynylcyclohexanol, ethynylmethyldecylcarbinol, 3-methyl-1-butyn-3-ol, and bis(2,2-dimethyl-3-butynoxy)dimethylsilane are preferred.

The amount of component (E) to be blended is preferably 0.01 to 2.0 parts by mass, more preferably 0.01 to 0.1 parts by mass, per 100 parts by mass of component (A). Within such a range, the effect of reaction control is sufficiently exhibited.

[6] Other Components The photocurable silicone adhesive composition used in the present invention may contain, in addition to the above components (A) to (E), the following other components as long as they do not impair the purpose of the present invention. may contain.
Other components include, for example, thixotropic agents such as fumed silica; reinforcing agents such as crystalline silica; antioxidants; light stabilizers; heat resistance improvers such as metal oxides and metal hydroxides; thermal conductivity imparting fillers such as alumina and crystalline silica; viscosity modifiers such as non-reactive silicone oils having no reactive functional groups; conductivity imparting agents such as metal powders such as silver and gold etc.

The photocurable silicone adhesive composition used in the present invention is prepared by mixing the above components (A) to (C), optional components (D) and (E), and other components by a known method. can be prepared by

[Method for manufacturing laminate]
A method for producing a laminate using the photocurable silicone adhesive composition described above will now be described.
The photocurable silicone adhesive composition is suitably used as a composition for forming an adhesive layer when two substrates constituting a laminate such as an optical device, display, or touch panel are laminated via an adhesive layer. can.
In this case, the method for manufacturing the laminate includes a coating step, a light irradiation step, a curing step, and a bonding step, and details of each step include, for example, the following.

(i) Coating Step In the coating step, the photocurable silicone adhesive composition described above is coated onto the substrate (first substrate).
Examples of the coating method include coating using slit coating, a DAM-Fill method, a fishbone method, and the like.
The coating amount is not particularly limited, but the amount is preferably such that the thickness of the silicone layer after curing is 100 to 5,000 μm.

Examples of the base material include polarizing materials and composite materials, metal members, plastic members, ceramic members, etc. In particular, casings for electrical applications, electronic applications, optical applications, etc., covering members, casting, bonding, sealing, etc. and is particularly useful for polarizing plates and polarizing films.
The photocurable silicone adhesive composition can also be used on substrates that have been activated by well-known pretreatment processes such as primer treatment, plasma treatment, and excimer light treatment.

(ii) Light irradiation step In the light irradiation step, the photocurable silicone adhesive composition is irradiated with light.
Examples of the light irradiation method include a method of using a lamp with a peak wavelength of 380 to 420 nm as a light source and irradiating an appropriate amount of light.
A 405 nm UV-LED lamp is preferred as the light source.
The light to be irradiated has a peak wavelength of 380 to 420 nm, preferably 395 to 410 nm, more preferably 405 nm.
The temperature during light irradiation is preferably 5 to 60°C, more preferably 5 to 35°C, from the viewpoints of curing speed and prevention of discoloration.
The irradiation intensity is preferably 300 to 2,000 mW/cm ² , and the irradiation dose is preferably 1,000 to 20,000 mJ/cm ² from the viewpoint of curability and workability.

(iii) Curing Step In the curing step, the composition irradiated with light is cured.
Although the curing method is not particularly limited, for example, a method of leaving the irradiated composition to stand in a predetermined environment to cure it, and forming an adhesive layer can be used.
The curing temperature is not particularly limited, but is preferably 5 to 60°C, more preferably 5 to 35°C, from the viewpoint of suppressing warpage and deterioration due to thermal expansion/contraction of the laminate.
The curing atmosphere is arbitrary, but an atmospheric atmosphere is preferred.
The curing time is not particularly limited, but is preferably about 1 minute to 24 hours.

(iv) Lamination step In the lamination step, the second substrate is laminated on the photocurable silicone adhesive composition or adhesive layer, and the two substrates are laminated together with the adhesive composition or adhesive layer. A laminated body is formed by bonding through the
The lamination method includes an adhesive layer-substrate laminate that has changed from a liquid state to a semi-solid state through the coating step, the light irradiation step and the curing step, a photocurable silicone adhesive composition after the coating step, or After the coating step and the light irradiation step, the photocurable silicone adhesive composition layer-substrate laminate is placed in a vacuum or atmospheric pressure bonding device, and the second substrate is coated with the photocurable silicone adhesive composition or For example, a method of laminating and bonding on an adhesive layer and, in the case of a composition, performing the remaining steps and curing to form a laminate.

The method for producing a laminate of the present invention is not affected by oxygen curing inhibition, and the curing time after light irradiation can be changed by the design and heating temperature of the adhesive composition. Therefore, flat displays and curved displays For example, it is possible to freely select and change the procedures of the coating process, the light irradiation process, the curing process, and the bonding process according to the structure of the device to be manufactured.

A specific example of the method for producing a laminate of the present invention is a method for producing a laminate having a cover panel and an image display panel.
First, the photocurable silicone composition of the present invention is applied onto the polarizing plate that constitutes the image display panel. Then, using a UV-LED lamp with a peak wavelength of 405 nm, the photocurable silicone composition was exposed to light with an irradiation intensity of 100 mW/cm ² at 25° C. for 100 seconds, with a dose of 10,000 nm. Irradiate to 000 mJ/cm ² . Subsequently, the silicone composition is cured by standing for 30 minutes in an environment of 25° C. to form an adhesive layer. After that, a cover panel is laminated on the adhesive layer by using a vacuum laminating device to obtain a laminate in which the cover panel and the image display panel are laminated via the adhesive layer.
In addition, after the light irradiation step, the image display panel and the cover panel are laminated via the silicone composition by first laminating the cover panel on the silicone composition using a vacuum laminating device, and then the temperature is maintained at 25°C. The silicone composition may be cured by standing for 30 minutes in an environment of . Alternatively, since the cover panel is transparent, vacuum bonding may be performed after the coating step, and then light irradiation may be performed through the cover panel to cure. Alternatively, a silicone composition that has been irradiated with light in advance may be applied to the image display panel, vacuum bonded to the cover panel, and cured.

EXAMPLES The present invention will be described in more detail below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
In the following examples, Mw represents the weight average molecular weight in terms of standard polystyrene by GPC measurement using THF solvent.

[Production Examples 1 and 2 and Comparative Production Examples 1 and 2]
A photocurable silicone composition was prepared by mixing the following components in the amounts (parts by mass) shown in Table 1.
(A) Component:
(A-1) Organopolysiloxane represented by the following average structural formula (3) (Mw: 28,000)

（式中、シロキサン単位の配列順は不定である。）

(In the formula, the arrangement order of the siloxane units is undefined.)

(A-2) Organopolysiloxane represented by the following average structural formula (4) (Mw: 22,400)

(A-3) Organopolysiloxane represented by the following average formula (5) (Mw: 16,500)
( _ViMe2Si ) _0.57 ( _Me3SiO ) _1.43 ( _Me2SiO ) ₂₂₀ (5)

(B) Component:
(B-1) Hydrodimethylsiloxy-blocked dimethylsiloxane Me _2.0 H _0.1 SiO _[1.9/2] represented by the following average composition formula (6) and having a kinematic viscosity of 17 mm ² /s at 23° C. (6)
(B-2) Hydrodimethylsiloxy-blocked dimethylsiloxane Me _1.8 H _0.3 SiO _[1.9/2] at both ends of the molecular chain, represented by the following average composition formula (7) and having a kinematic viscosity of 27 mm ² /s at 23°C. (7)
(B-3) Hydrodimethylsiloxy-blocked dimethylsiloxane Me _1.7 H _0.4 SiO _[1.9/2] represented by the following average composition formula (8) and having a kinematic viscosity of 105 mm ² /s at 23° C. (8)

(C) Component:
(C-1) 2-(2-butoxyethoxy)ethyl acetate solution of bisacetylacetonatoplatinum complex (platinum content 0.5% by mass)
(C-2) Comparative component Toluene solution of trimethyl(methylcyclopentadienyl)platinum complex (platinum content 0.5% by mass)

Component (D): Adhesion aid (D-1) 7-octenyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-1083)
(D-2) a compound represented by the following structural formula (10)

(D-3) a compound represented by the following structural formula (11)

(E) component: reaction control agent (E-1) compound represented by the following formula (9)

Other Ingredients:
Fumed silica (Aerosil NSX-200 (average primary particle size 8 nm), Nippon Aerosil Co., Ltd.)

[Examples 1 and 2 and Comparative Examples 1 to 4]
The photocurable silicone adhesive compositions prepared in each of the production examples and comparative production examples above were evaluated for gelling time by the following method. Table 2 shows the results.
[Gelling time]
The gelation time was measured using a viscoelasticity measuring device ARES-G2 (manufactured by TA Instruments Japan Co., Ltd.) equipped with a UV curing accessory.
1 ml of each photocurable silicone composition prepared is applied onto a stainless steel plate or onto each of the following polarizing plates fixed on this plate, and a UV-LED lamp with a peak wavelength of 365 nm (Panasonic Corporation ANOJ6186 manufactured by Panasonic Corporation) or a UV-LED lamp with a wavelength of 405 nm (ANOJ6189 manufactured by Panasonic Corporation) was used to irradiate each composition with light of 100 mW/cm ² at 25° C. so as to obtain 10,000 mJ/cm ² . .
After that, the temperature was kept at 25° C. and the viscoelasticity was measured. The time (minutes) required from the completion of UV irradiation until tan δ=1 was defined as the gelling time.

Polarizing plate 1: NPF-CWQ1463VCU manufactured by Nitto Denko Corporation
Polarizing plate 2: NAZ-EFCWQVAG15AR manufactured by Nitto Denko Corporation
Polarizing plate 3: NAZ-EFCWQVAG150 manufactured by Nitto Denko Corporation
Polarizing plate 4: NPF-CWQ1463VCUAG15ARS manufactured by Nitto Denko Corporation
Polarizing plate 5: NPF-SWQ1423CUARC380 manufactured by Nitto Denko Corporation
Polarizing plate 6: NPF-CWQ1463VCUAG150 manufactured by Nitto Denko Corporation

As shown in Table 2, according to the method for producing a laminate of the present invention, the photocurable silicone composition rapidly cures at 25° C. regardless of the type of polarizing plate that comes into contact with it, and the composition can be used for touch panels, displays, and the like. It can be said that it was shown that it can be suitably used for bonding image display devices.
On the other hand, in Comparative Examples 1 and 2 using an addition reaction catalyst other than the component (C) of the present invention, curing by light irradiation using an LED light source with a peak wavelength of 405 nm did not occur, and the light source in Examples 1 and 2 peaked. It can be seen that in Comparative Examples 3 and 4 in which the LED light source with a wavelength of 365 nm was used, curing inhibition caused by the polarizing plate may occur.

Claims (8)

A method for producing a laminate comprising a first base material and an adhesive layer laminated on the first base material,
A laminate characterized in that the adhesive layer is formed by irradiating and curing a photocurable silicone composition containing the following components (A) to (C) with light having a peak wavelength of 380 to 420 nm. Production method.
(A) Linear organopolysiloxane represented by the following average formula ( ¹ ): 100 parts by mass (R1R22SiO1 _/2 ⁾ _a ( _{R23SiO1 /2 )} ² _{- a} (Ar2 _SiO2 / ² ) _b ( _{R22SiO2 /2} ) _c (1)
{wherein each R ¹ independently represents a substituted or unsubstituted alkenyl group, each R ² independently represents a substituted or unsubstituted alkyl group, and each Ar independently represents represents a substituted or unsubstituted aryl group, a represents a number of 0.3 to 2, b is 0 to 100, c is 1 to 1,000, and b / (b + c) = 0 to 0 Represents a number that satisfies .7. }
(B) Organohydrogenpolysiloxane having at least two Si—H bonds in one molecule, represented by the following average compositional formula (2): 1 to 200 parts by mass R ³ _d H _e SiO _{[(4- de)/2]} (2)
(wherein each R ³ independently represents a substituted or unsubstituted monovalent hydrocarbon group excluding an aliphatic unsaturated hydrocarbon group; d and e are 0.7≤d≤2.5; represents a number that satisfies 0.01≦e≦1.0 and 0.8≦d+e≦2.7.)
(C) a platinum compound having at least one of a β-diketonato group, a β-ketoesterate group, and a 1,3-diesterate group as a ligand 2. The method for producing a laminate according to claim 1, wherein the component (C) is bisacetylacetonatoplatinum (II). (i) a coating step of coating the photocurable silicone composition on the surface of the first substrate;
(ii) a light irradiation step of irradiating the photocurable silicone composition with light having a peak wavelength of 380 to 420 nm;
(iii) a curing step of curing the photocurable silicone composition to form an adhesive layer;
(iv) A second substrate is laminated on the photocurable silicone composition or adhesive layer, and the first and second substrates are bonded together via the photocurable silicone composition or adhesive layer. 3. The method for manufacturing a laminate according to claim 1, further comprising a bonding step. The method for producing a laminate according to claim 3, wherein the curing step is performed at 5 to 35°C. 5. The method for producing a laminate according to claim 3, wherein said second base material is a polarizing plate or a polarizing film. The method for producing a laminate according to any one of claims 1 to 5, wherein the first base material is a polarizing plate or a polarizing film. 7. The method for producing a laminate according to any one of claims 1 to 6, wherein the light has a peak wavelength of 405 nm. The method for producing a laminate according to any one of claims 1 to 7, wherein the laminate is an image display device.