Organopolysiloxane composition, and semi-cured and cured products prepared therefrom

Abstract

[Problem] To provide a hydrosilylation-reactive composition that has a sufficient pot life at room temperature but can be cured at low temperatures by high-energy radiation, and the semi-cured product is stable during curing. Also provided are a semi-cured product and a cured product obtained using the same. [Solution] A composition containing (A) a compound containing at least one aliphatic unsaturated monovalent hydrocarbon group per molecule, (B) a compound containing at least two silicon-bonded hydrogen atoms per molecule, (C) a first hydrosilylation catalyst that is active in the composition without high-energy radiation, and (D) a second hydrosilylation catalyst that is inactive in the absence of high-energy radiation but is active in the composition upon high-energy radiation.

Description

[Technical Field]

[0001] The present invention relates to organopolysiloxane compositions that can be cured by a hydrosilylation reaction, as well as semi-cured and cured products prepared therefrom. [Background technology]

[0002] Silicone materials have excellent properties such as heat resistance, chemical resistance, and electrical insulation, and are therefore used in a variety of applications. Silicone materials can be formed on a variety of substrates, including plastics, metals, glass, ceramics, paper, and wood, and are used in a wide range of applications, including everyday items, medical supplies, and electronic products. Silicone materials are typically obtained by crosslinking organopolysiloxanes through a hydrosilylation reaction. For ease of use, a transition metal complex catalyst that is activated by heat is typically used in the hydrosilylation reaction. However, when forming a silicone material on a substrate such as a thermoplastic resin film, the substrate cannot be heated to a high temperature, so a catalyst that is activated by irradiation with high-energy rays such as ultraviolet light is used (Patent Document 1).

[0003] However, organopolysiloxane compositions using high-energy ray-activated catalysts do not cure immediately upon irradiation with high-energy rays, and heating is often required to cure them in a short time. Increasing the amount of catalyst to cure them in a short time results in the problem of discoloration of the cured product, and curing at low temperatures with a low amount of catalyst results in the problem of incomplete curing reaction, resulting in a cured product with low mechanical strength. On the other hand, in order to complete curing at low temperatures with a heat-activated catalyst, the amount of catalyst must be increased, which not only results in the problem of discoloration upon curing, but also in the problem of very rapid viscosity increase and a short usable life at room temperature. On the other hand, curing at low temperatures with a low amount of catalyst results in the problem of incomplete curing reaction, resulting in a cured product with low mechanical strength.

[0004] Furthermore, when attempting to stably obtain a thickened body or thermoplastic body in the process of curing by carrying out a hydrosilylation reaction in stages, if a heat-activated catalyst is used alone, a high-temperature reaction is required for curing, whereas if a high-energy ray-activated catalyst is used alone, the first-stage hydrosilylation reaction cannot be controlled, making it difficult to stably obtain a thickened body or thermoplastic body.

[0005] Furthermore, when using only a high-energy ray activated catalyst, curing occurs only in the areas irradiated with high-energy rays, and in practice there is a problem that areas that are shielded from the high-energy ray irradiation do not cure. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 5-239216 Summary of the Invention [Problem to be solved by the invention]

[0007] Therefore, an object of the present invention is to provide a composition that can be cured at low temperatures by irradiation with high-energy rays while having a sufficient pot life at room temperature, and the resulting thickened body or thermoplastic body during curing is stable and has good subsequent workability. [Means for solving the problem]

[0008] The composition of the present invention contains (A) a compound containing at least one aliphatic unsaturated monovalent hydrocarbon group per molecule, (B) a compound containing at least two silicon-bonded hydrogen atoms per molecule, (C) a first hydrosilylation catalyst that is active in the composition without high-energy radiation, and (D) a second hydrosilylation catalyst that is inactive in the absence of high-energy radiation but is active in the composition upon high-energy radiation.

[0009] The high-energy radiation is preferably any one selected from ultraviolet rays, X-rays, and electron beams. At least one of the components (A) and (B) is preferably an organopolysiloxane.

[0010] The component (A) is represented by the following average composition formula (1): R 1 a R 2 b SiO (4-a―b) / 2 (1) (In the formula, R 1 is an alkenyl group having 2 to 12 carbon atoms, and R 2 is a group selected from monovalent hydrocarbon groups having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, hydroxyl groups, and alkoxy groups, and a and b are numbers that satisfy the following conditions: 1≦a+b≦3 and 0.001≦a / (a+b)≦0.33; The component (B) is represented by the following average composition formula (2): H c R 3 d SiO (4-c-d) / 2 (2) (In the formula, R 3 is a group selected from monovalent hydrocarbon groups having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, hydroxyl groups, and alkoxy groups, and c and d are numbers that satisfy the following conditions: 1≦c+d≦3 and 0.01≦c / (c+d)≦0.33. Preferably, the organopolysiloxane is represented by the formula:

[0011] Furthermore, the component (B) has the following average unit formula (3): (HR 4 2SiO 1 / 2 ) e (R 4 3SiO 1 / 2 ) f (HR 4 SiO 2 / 2 ) g (R 4 2SiO 2 / 2 ) h (HSiO 3 / 2 ) i (R4 SiO 3 / 2 ) j (SiO 4 / 2 ) k (R 5 O 1 / 2 ) l (3) (In the formula, R 4 is a group selected from monovalent hydrocarbon groups having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, hydroxyl groups, and alkoxy groups, and R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and e, f, g, h, i, j, k, and l are numbers that satisfy the following conditions: e+f+g+h+i+j+k=1, 0≦l≦0.1, 0.01≦e+g+i≦0.2, 0.01≦e≦0.6, 0.01≦g≦0.6, 0≦i≦0.4, 0.01≦e+f≦0.8, 0.01≦g+h≦0.8, 0≦i+j≦0.6) Preferably, the organohydrogenpolysiloxane is represented by the following formula:

[0012] The molar ratio ((C) / (D)) of the component (C) to the component (D) is preferably 0.001 to 1000. The component (C) is preferably at least one transition metal complex catalyst selected from platinum, palladium, rhodium, nickel, iridium, ruthenium, and iron complexes, and the component (D) is preferably at least one selected from (substituted and unsubstituted cyclopentadienyl)trimethylplatinum(IV), β-diketonatetrimethylplatinum(IV), and bis(β-diketonate)platinum(II).

[0013] Another aspect of the present invention relates to a semi-cured product obtained by subjecting the composition to a first hydrosilylation reaction without irradiation with high-energy rays.

[0014] Yet another aspect of the present invention relates to a cured product obtained by irradiating the semi-cured product with high-energy rays. [Effects of the Invention]

[0015] The composition of the present invention has a sufficient pot life at room temperature, yet can be cured at a low temperature starting from high-energy ray irradiation, and can stably give a thickened body or thermoplastic body during curing. Furthermore, it can be cured over time even in areas that are shielded from high-energy ray irradiation. DETAILED DESCRIPTION OF THE INVENTION

[0016] (composition) The composition of the present invention contains the following components (A) to (D), which will be described in order below. Component (A) The composition of the present invention contains a compound (component (A)) containing at least one aliphatic unsaturated monovalent hydrocarbon group per molecule. Component (A) is a compound containing an aliphatic unsaturated monovalent hydrocarbon group to which a hydrosilyl group (—SiH) is added during a hydrosilylation reaction. Examples of component (A) include linear or branched organopolysiloxanes containing alkenyl groups, polyethers containing alkenyl groups, polyolefins containing alkenyl groups, and polyesters containing alkenyl groups. Of these, organopolysiloxanes having the following average compositional formula (1) are preferred. R 1 a R 2 b SiO (4-a―b) / 2 (1)

[0017] In general formula (1), R 1 R is an alkenyl group having 2 to 12 carbon atoms. Specific examples include vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl groups, and among these, vinyl, allyl, and hexenyl groups are preferred. 2is a group selected from monovalent hydrocarbon groups having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, hydroxyl groups, and alkoxy groups. Some of the hydrogen atoms of the monovalent hydrocarbon groups having 1 to 12 carbon atoms may be substituted with halogen atoms or hydroxyl groups. Examples of monovalent hydrocarbon groups having 1 to 12 carbon atoms include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; aryl groups such as phenyl, tolyl, xylyl, naphthyl, anthracenyl, phenanthryl, and pyrenyl; aralkyl groups such as benzyl, phenethyl, naphthylethyl, naphthylpropyl, anthracenylethyl, phenanthrylethyl, and pyrenylethyl; and groups in which a hydrogen atom of these aryl or aralkyl groups has been substituted with an alkyl group such as methyl or ethyl; an alkoxy group such as methoxy or ethoxy; or a halogen atom such as chlorine or bromine.

[0018] a and b are numbers that satisfy the following conditions: 1≦a+b≦3 and 0.001≦a / (a+b)≦0.33, and preferably the following conditions: 1.5≦a+b≦2.5 and 0.005≦a / (a+b)≦0.2. This is because when a+b is 1 or more, the flexibility of the cured product is increased, while when a+b is 3 or less, the mechanical strength of the cured product is increased. Furthermore, when a / (a+b) is 0.001 or more, the mechanical strength of the cured product is increased, while when it is 0.33 or less, the flexibility of the cured product is increased.

[0019] The molecular structure of such organopolysiloxanes may be linear, branched, or cyclic, and the organopolysiloxane may be a mixture of one or more compounds having such molecular structures.

[0020] Such component (A) includes compounds represented by the general formula: R 6 3SiO(R 6 2SiO) m1 SiR 6 3 Linear organopolysiloxanes and / or polymers having the average unit formula: (R 6 SiO 3 / 2 ) g1 (R 6 2SiO 2 / 2 ) h1 (R 6 3SiO 1 / 2 ) i1 (SiO 4 / 2 ) j1 (XO 1 / 2 ) k1 In the formula, each R 6 are independently unsubstituted or halogen-substituted monovalent hydrocarbon groups, and examples thereof include the same groups as those described above. However, at least two R 6 is an alkenyl group. The alkenyl group is preferably a vinyl group. In addition, since the attenuation of light due to refraction, reflection, scattering, etc. of the resulting cured product is small, it is preferable that all R 6 At least 30 mol % of the groups are aryl groups, and preferably at least 40 mol % are aryl groups. The aryl groups are preferably phenyl groups. In the formula, m1 is an integer ranging from 5 to 1,000. In the formula, g1 is a positive number, h1 is 0 or a positive number, i1 is 0 or a positive number, j1 is 0 or a positive number, k1 is 0 or a positive number, and h1 / g1 is a number ranging from 0 to 10, i1 / g1 is a number ranging from 0 to 5, j1 / (g1+h1+i1+j1) is a number ranging from 0 to 0.3, and k1 / (g1+h1+i1+j1) is a number ranging from 0 to 0.4.

[0021] (B) Component Component (B) is a compound containing at least two silicon-bonded hydrogen atoms per molecule, and contains a hydrosilyl group (—SiH) that is added to the aliphatic unsaturated group in component (A) during the hydrosilylation reaction. Component (B) is preferably an organopolysiloxane having the following average compositional formula (2):

[0022] H c R 3d SiO (4-c-d) / 2 (2)

[0023] In general formula (2), R 3 is a group selected from monovalent hydrocarbon groups having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, hydroxyl groups, and alkoxy groups. Some of the hydrogen atoms in the monovalent hydrocarbon group having 1 to 12 carbon atoms may be substituted with halogen atoms or hydroxyl groups. Examples of monovalent hydrocarbon groups having 1 to 12 carbon atoms include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; aryl groups such as phenyl, tolyl, xylyl, naphthyl, anthracenyl, phenanthryl, and pyrenyl; aralkyl groups such as benzyl, phenethyl, naphthylethyl, naphthylpropyl, anthracenylethyl, phenanthrylethyl, and pyrenylethyl; and groups in which hydrogen atoms in these aryl or aralkyl groups have been substituted with alkyl groups such as methyl and ethyl; alkoxy groups such as methoxy and ethoxy; or halogen atoms such as chlorine and bromine. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentanoxy, hexanoxy, and octanoxy.

[0024] c and d are numbers that satisfy the following conditions: 1≦c+d≦3 and 0.01≦c / (c+d)≦0.33, and preferably the following conditions: 1.5≦c+d≦2.5 and 0.05≦c / (c+d)≦0.2. This is because when c+d is 1 or greater, the flexibility of the cured product is high, while when it is 3 or less, the mechanical strength of the cured product is high. Furthermore, when c / (c+d) is 1.5 or greater, the mechanical strength of the cured product is high, while when it is 2.5 or less, the flexibility of the cured product is high.

[0025] There are no limitations on the viscosity of the organopolysiloxane having the average composition formula represented by general formula (2) above, but the viscosity at 25°C is preferably within the range of 0.5 to 10,000 mPa·s, and particularly preferably within the range of 1 to 1,000 mPa·s.

[0026] Examples of organopolysiloxanes having the average composition formula of general formula (2) include 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, tris(dimethylhydrogensiloxy)methylsilane, tris(dimethylhydrogensiloxy)phenylsilane, 1-(3-glycidoxypropyl)-1,3,5,7-tetramethylcyclotetrasiloxane, 1,5-di(3-glycidoxypropyl)-1,3,5,7-tetramethylcyclotetrasiloxane, 1-(3-glycidoxypropyl)-5-trimethoxysilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, and siloxanes having trimethylsilyl groups at both ends of the molecular chain. Methylhydrogenpolysiloxane capped with methylsiloxy groups, copolymer of dimethylsiloxane and methylhydrogensiloxane capped with trimethylsiloxy groups at both ends of the molecular chain, dimethylpolysiloxane capped with dimethylhydrogensiloxane, copolymer of dimethylsiloxane and methylhydrogensiloxane capped with dimethylhydrogensiloxane at both ends of the molecular chain, copolymer of methylhydrogensiloxane and diphenylsiloxane capped with trimethylsiloxy groups at both ends of the molecular chain, copolymer of methylhydrogensiloxane, diphenylsiloxane and dimethylsiloxane capped with trimethylsiloxy groups at both ends of the molecular chain, hydrolysis condensate of trimethoxysilane, (CH3)2HSiO 1 / 2 Units and SiO 4 / 2 A copolymer consisting of (CH3)2HSiO units 1 / 2 Units and SiO 4 / 2 Units and (C6H5)SiO 3 / 2 Examples include copolymers consisting of these units, and mixtures of two or more of these units.

[0027] Further examples of organopolysiloxanes having the average composition formula represented by general formula (2) above include the following organopolysiloxanes: In the formula, Me and Ph represent a methyl group and a phenyl group, respectively, m2 is an integer from 1 to 100, n2 is an integer from 1 to 50, and b2, c2, d2, and e2 are each positive numbers, with the proviso that the sum of b2, c2, d2, and e2 in one molecule is 1. HMe2SiO(Ph2SiO) m2 SiMe2H HMePhSiO(PhSiO) m2 SiMePhH HMePhSiO(PhSiO) m2 (MePhSiO) n2 SiMePhH HMePhSiO(PhSiO) m2 (Me2SiO) n2 SiMePhH (HMe2SiO 1 / 2 ) b2 (PhSiO 3 / 2 ) c2 (HMePhSiO 1 / 2 ) b2 (PhSiO 3 / 2 ) c2 (HMePhSiO 1 / 2 ) b2 (HMe2SiO 1 / 2 ) c2 (PhSiO 3 / 2 ) d2 (HMe2SiO 1 / 2 ) b2 (Ph2SiO 2 / 2 ) c2 (PhSiO 3 / 2 ) d2 (HMePhSiO 1 / 2 ) b2 (Ph2SiO 2 / 2 ) c2 (PhSiO 3 / 2 ) d2 (HMePhSiO 1 / 2 ) b2 (HMe2SiO 1 / 2 )c2 (Ph2SiO 2 / 2 ) d2 (PhSiO 3 / 2 ) e2

[0028] The component (B) is preferably an organohydrogenpolysiloxane represented by the average unit formula shown in the following general formula (3).

[0029] (HR 4 2SiO 1 / 2 ) e (R 4 3SiO 1 / 2 ) f (HR 4 SiO 2 / 2 ) g (R 4 2SiO 2 / 2 ) h (HSiO 3 / 2 ) i (R 4 SiO 3 / 2 ) j (SiO 4 / 2 ) k (R 5 O 1 / 2 ) l (3)

[0030] In general formula (3), R 4 is a group selected from monovalent hydrocarbon groups having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, hydroxyl groups, and alkoxy groups. The monovalent hydrocarbon groups having 1 to 12 carbon atoms, hydroxyl groups, and alkoxy groups are the same as those described above. R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, and a hexyl group. e, f, g, h, i, j, k, and l are numbers that satisfy the following conditions: e+f+g+h+i+j+k=1, 0≦l≦0.1, 0.01≦e+g+i≦0.2, 0≦e≦0.6, 0≦g≦0.6, 0≦i≦0.4, 0.01≦e+f≦0.8, 0.01≦g+h≦0.8, 0≦i+j≦0.6.

[0031] In addition, the above-mentioned "HR4 2SiO 1 / 2 "," "R 4 3SiO 1 / 2 ", "HR 4 SiO 2 / 2 "," "R 4 2SiO 2 / 2 ", "HSiO 3 / 2 "," "R 4 SiO 3 / 2 " and "SiO 4 / 2 Each constituent unit of " is M H Unit, M unit, D H Units, D Units, T H These are the partial structural units of organohydrogenpolysiloxanes, called "R units," "T units," and "Q units." 5 O 1 / 2 " is a D unit, D H Units, TUnits, T H It is a group that bonds to an oxygen atom in an organopolysiloxane, or a silicon-bonded hydroxyl group (Si—OH) in the organopolysiloxane, or a silicon-bonded alkoxy group that remains unreacted during the production of the organopolysiloxane. H The units are mainly present at the molecular chain terminals of organohydrogenpolysiloxane, and D H The units are present in the molecular chain of the organohydrogenpolysiloxane.

[0032] The content of component (B) is an amount such that the number of silicon-bonded hydrogen atoms in this component is in the range of 0.1 to 5 moles, and preferably in the range of 0.5 to 2 moles, per mole of total alkenyl groups in component (A).This is because if the content of component (B) is at or above the lower limit of the above range, the mechanical strength of the cured product will be high, and if it is at or below the upper limit of the above range, the flexibility of the cured product will be high.

[0033] (C) Component Component (C) is a first hydrosilylation catalyst that exhibits activity in the composition without exposure to high-energy radiation. Component (C) is a hydrosilylation reaction catalyst that semi-cures the composition. "Semi-cured" refers to a thickened material that is fluid at room temperature or a thermoplastic material that is non-fluid at room temperature but fluid at 100°C. A thickened material means that the viscosity at 25°C is between 1.5 and 100 times the initial viscosity of the composition. A thermoplastic material means that the viscosity at 100°C is 1,000,000 mPa·s or less.

[0034] Examples of the first hydrosilylation catalyst include platinum catalysts, rhodium catalysts, palladium catalysts, nickel catalysts, iridium catalysts, ruthenium catalysts, and iron catalysts, with platinum catalysts being preferred. Examples of platinum catalysts include platinum fine powder, platinum black, platinum-supported silica fine powder, platinum-supported activated carbon, chloroplatinic acid, alcohol solutions of chloroplatinic acid, platinum olefin complexes, platinum alkenylsiloxane complexes, and other platinum compounds, with platinum alkenylsiloxane complexes being particularly preferred. Examples of this alkenylsiloxane include 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, alkenylsiloxanes in which some of the methyl groups of these alkenylsiloxanes have been substituted with ethyl groups, phenyl groups, etc., and alkenylsiloxanes in which the vinyl groups of these alkenylsiloxanes have been substituted with allyl groups, hexenyl groups, etc. 1,3-divinyl-1,1,3,3-tetramethyldisiloxane is particularly preferred because the platinum-alkenylsiloxane complex has good stability. Furthermore, it is preferable to add to the platinum-alkenylsiloxane complex an alkenylsiloxane such as 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3-diallyl-1,1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,3-dimethyl-1,3-diphenyldisiloxane, 1,3-divinyl-1,1,3,3-tetraphenyldisiloxane, or 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, or an organosiloxane oligomer such as a dimethylsiloxane oligomer, because this can improve the stability of the platinum-alkenylsiloxane complex. The addition of an alkenylsiloxane is particularly preferable.

[0035] The catalyst for component (C) is a catalyst that is active without exposure to high-energy rays, but is preferably one that is active even at relatively low temperatures. Specifically, it is active in the composition at temperatures ranging from 0 to 200°C and promotes the hydrosilylation reaction. The amount of component (C) varies depending on the type of catalyst and the type of composition, but is usually an amount that results in the metal atoms in the catalyst being in the range of 0.01 to 50 ppm by mass, preferably 0.1 to 30 ppm, relative to the composition.

[0036] (D) Component Component (D) is a second hydrosilylation catalyst that is inactive in the absence of high-energy radiation but becomes active in the composition upon high-energy radiation. Component (D) is a so-called high-energy radiation-activated catalyst or photoactivated catalyst, and is well known in the art.

[0037] Here, high-energy rays refer to ultraviolet rays, gamma rays, X-rays, alpha rays, electron beams, etc., with ultraviolet rays, X-rays, and electron beams emitted from commercially available electron beam irradiation devices being preferred. Industrially, ultraviolet rays with wavelengths in the range of 280 to 380 nm are conveniently used. The dose of ultraviolet rays varies depending on the type of high-energy ray-activated catalyst, but in the case of ultraviolet rays, the cumulative dose at a wavelength of 365 nm is preferably in the range of 100 mJ / cm2 to 10 J / cm2.

[0038] Specific examples of component (D) include (methylcyclopentadienyl)trimethylplatinum(IV), (cyclopentadienyl)trimethylplatinum(IV), (1,2,3,4,5-pentamethylcyclopentadienyl)trimethylplatinum(IV), (cyclopentadienyl)dimethylethylplatinum(IV), (cyclopentadienyl)dimethylacetylplatinum(IV), (trimethylsilylcyclopentadienyl)trimethylplatinum(IV), (methoxycarbonylcyclopentadienyl)trimethylplatinum(IV), (dimethylphenylsilylcyclopentadienyl)trimethylcyclopentadienylplatinum(IV), trimethyl(acetylacetonato)platinum(IV), trimethyl(3,5-heptamethylcyclopentadienyl)trimethylplatinum(IV), and trimethyl(3,5-heptamethylcyclopentadienyl)trimethylplatinum(IV). Examples of suitable platinum bis(2,4-pentanedionato)platinum(II), bis(2,4-hexanedionato)platinum(II), bis(2,4-heptanedionato)platinum(II), bis(3,5-heptanedionato)platinum(II), bis(1-phenyl-1,3-butanedionato)platinum(II), bis(1,3-diphenyl-1,3-propanedionato)platinum(II), and bis(hexafluoroacetylacetonato)platinum(II). Of these, (methylcyclopentadienyl)trimethylplatinum(IV) and bis(2,4-pentanedionato)platinum(II) are preferred in terms of versatility and ease of availability.

[0039] The content of component (D) is the amount necessary to further cure the composition semi-cured with component (C), and is preferably an amount such that the metal atoms in this catalyst are in the range of 1 to 50 ppm by mass, and more preferably in the range of 5 to 30 ppm, relative to the composition.

[0040] The molar ratio of component (C) to component (D) ((C) / (D)) is usually 0.001 to 1000, and preferably 0.01 to 100. When the molar ratio is equal to or less than the upper limit, the curing reaction by high-energy radiation can be accelerated, and when the molar ratio is equal to or more than the lower limit, the curing reaction can be carried out in a short time at a low temperature.

[0041] The organopolysiloxane composition used in the present invention does not necessarily contain a hydrosilylation reaction inhibitor. Typically, a hydrosilylation reaction inhibitor is added to a composition to improve the pot life of the composition and obtain a stable composition. However, in the present invention, a stable composition can be obtained without the addition of a hydrosilylation reaction inhibitor, and it is preferable that the addition of a hydrosilylation reaction inhibitor does not slow the curing reaction. When a hydrosilylation reaction inhibitor is contained, it may contain compounds such as alkyne alcohols such as 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, and 2-phenyl-3-butyn-2-ol; eneyne compounds such as 3-methyl-3-penten-1-yne and 3,5-dimethyl-3-hexen-1-yne; 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, and benzotriazole.

[0042] (E) Component If necessary, other organopolysiloxanes, adhesion promoters, inorganic fillers such as silica, glass, alumina, and zinc oxide, fine powders of organic resins such as polymethacrylate resins, phosphors, heat stabilizers, dyes, pigments, flame retardants, solvents, etc. may be added to the organopolysiloxane composition used in the present invention. The amounts and methods of addition are known to those skilled in the art.

[0043] The present composition can be prepared by uniformly mixing components (A) to (D) and, if necessary, other optional components. When preparing the present composition, the components can be mixed at room temperature using various types of stirrers or kneaders, or, if necessary, can be mixed under heating. There are also no limitations on the order in which the components are added, and they can be mixed in any order.

[0044] The composition of the present invention may be prepared, for example, by adding and mixing component (D) while heating and kneading components (A) to (C) at a temperature range of 80°C to 120°C. Within this temperature range, the entire composition softens, allowing component (D) to be uniformly dispersed throughout, which is particularly beneficial in preventing poor curing during molding into sheets and partial cohesive failure during adhesion. On the other hand, temperatures below the lower limit may result in insufficient softening, making it difficult to uniformly disperse component (D) throughout, even with mechanical force. Conversely, temperatures above the upper limit may be undesirable because component (D) may react during mixing, resulting in significant thickening or hardening of the entire composition. The powder mixer used in this production method is not limited, and examples include single- or double-screw continuous mixers, twin-roll mixers, Ross mixers, Hobart mixers, dental mixers, planetary mixers, kneader mixers, lab mills, small pulverizers, and Henschel mixers. Lab mills, small pulverizers, and Henschel mixers are preferred.

[0045] The composition can be a one-liquid composition in which all components are blended in the same container, or, taking storage stability into consideration, a two-liquid composition in which components are mixed at the time of use.

[0046] (semi-cured product) Another aspect of the present invention relates to a semi-cured product obtained by subjecting the composition to a first hydrosilylation reaction without irradiating it with high-energy radiation.

[0047] The first hydrosilylation reaction may be accelerated, in some cases, by heating the composition at a temperature of less than 150° C., preferably less than 125° C., and more preferably less than 100° C. The heating time varies depending on the types and amounts of each component in the composition, but is usually 0.2 to 4 hours, and preferably 0.5 to 2 hours.

[0048] Through the above process, the composition becomes a semi-cured product. As described above, a semi-cured product means a thickened material that is fluid at room temperature, or a thermoplastic material that is non-fluid at room temperature but fluid at 100°C. The meanings of thickened material and thermoplastic material are as described above.

[0049] (cured product) The cured product is obtained by irradiating the semi-cured product with high-energy radiation to carry out a second hydrosilylation reaction. The types of high-energy radiation are as described above. The radiation dose varies depending on the type of high-energy radiation-activated catalyst. In the case of ultraviolet radiation, the cumulative radiation dose at 365 nm is 100 mJ / cm. 2 ~10J / cm 2 It is preferable that the range is within the range of

[0050] The cured product of the present invention can be used as a variety of materials. Here, "cured product" means that it does not flow even when heated to 200°C or higher. The hardness of this cured product is not particularly limited, but it usually ranges from a gel with a penetration of 70 or less to a resin with a Shore D hardness of 80.

[0051] The cured product formed by the method of the present invention exhibits excellent physical properties, particularly excellent mechanical strength. Furthermore, since the method of the present invention produces a cured product through a stable semi-cured state, it can be used for various applications such as adhesives, sealants, and pressure-sensitive adhesives. In particular, the cured product formed by the method of the present invention has high light transmittance, so it can be used for applications such as image display devices, lighting devices, and light-receiving elements.

[0052] The present cured product can be formed, for example, by coating the present composition on a film-, tape-, or sheet-like substrate, followed by high-energy radiation, leaving at room temperature, or heating at low temperature to induce a hydrosilylation reaction and promote curing. Alternatively, the present composition can be placed between two substrates and cured to firmly bond the two substrates, or by smoothly coating the present composition on at least one surface of the substrate, semi-curing it to make it non-fluid, and then laminating the two substrates together and further curing to firmly bond them. The film thickness of the cured product is not limited, but is preferably 1 to 100,000 μm, more preferably 50 to 30,000 μm.

[0053] The present composition can be cured at a relatively low temperature range, including room temperature (for example, in the range of 15 to 80°C). The curing reaction of the present composition can be adjusted to the desired rate by adjusting the concentration of the catalytic metal in component (C) and the type and content of the hydrosilylation reaction retarder described above.

[0054] This composition is useful as a variety of potting agents, sealants, and adhesives, preferably as an optical adhesive, and particularly as an optical adhesive for displays. The cured product exhibits little coloration and is resistant to clouding at high temperatures or high temperatures and humidity, making it suitable as a material for forming an intermediate layer between the image display area and the protective area of a display.

[0055] The present composition can be used not only in liquid crystal displays but also in the general display field, such as organic EL displays, electronic paper displays, plasma displays, etc. The use of the present composition in such fields will be described later.

[0056] Because this composition cures at relatively low temperatures, it can also be used to coat substrates with poor heat resistance. Such substrates are typically transparent substrates such as glass, synthetic resin films and sheets, and transparent electrode coatings. Examples of coating methods for this composition include dispensing, gravure coating, microgravure coating, slit coating, slot die coating, screen printing, stencil printing, and comma coating.

[0057] The cured product of the present invention can also be suitably used for producing a laminate. The laminate is preferably at least one type selected from a display device, an electronic component, or a solar cell module, and is particularly preferably a display device such as an optical display.

[0058] In the optical display according to an embodiment of the present invention, the visibility of the optical display can be improved by bonding or adhering between the display unit such as a liquid crystal or organic EL display and a display-forming member such as a touch panel or cover lens, or between the display-forming members themselves, using a cured product of the curable silicone composition of the present invention.

[0059] The image display surface of the display may be flat (planar) or curved. The optical display may be a cathode ray tube (CRT) display or a flat panel display (FPD). Examples of FPDs include non-emissive display devices such as LCDs and electrochromic displays (ECDs), electroluminescent displays (ELDs) such as organic EL displays and inorganic EL displays, plasma displays (PDPs), field emission displays (FEDs) such as surface-conduction electron-emitter displays (SEDs), and light-emitting display devices such as LED displays.

[0060] Hereinafter, a method for producing a laminate according to an embodiment of the present invention will be described. In the following production method, the optical member refers to a member generally used as a component of an optical display. More specifically, the optical member may be, for example, a lens (which may be made of resin or glass), an optical sheet-like member (including a color filter, a polarizing plate, a retardation plate, a viewing angle widening film, a brightness improving film, a reflective sheet, and a transparent conductive film), an optical protective material which may be transparent (such as a transparent protective material (transparent protective film) made of glass, resin, or a resin coating layer), a front display panel, a touch panel (made of glass or resin), or a transparent electrode layer such as an ITO or ATO film. Needless to say, the surface of the display panel or touch panel may further comprise an optical protective material. Furthermore, the optical member may be a backlight unit itself including a light-emitting layer and a display surface (display panel) as described below, or may be a component in which the entire optical member is made of an independent laminated member or a module within a display device such as a touch panel, and the optical member may further include an adhesive layer 15 made of the present cured product. That is, the concept of optical members includes image display panels, optical panels, front panels, backlight units, touch panel units, and the like, which will be described later.

[0061] A method for producing a laminate according to one embodiment of the present invention includes a placement and lamination step in which the above-described composition is placed on one or both surfaces of at least one of two optical components and the two optical components are laminated together via the curable silicone composition; and a curing step in which the composition is left standing or heated to promote a hydrosilylation reaction and thereby cure the composition.

[0062] In the above-mentioned disposing step, the present composition is disposed on a member using, for example, the above-mentioned coating method. In the above-mentioned disposing step, the present composition may be disposed on one surface of one optical member. In addition, the cured product disposed on both surfaces of the optical member that is not used for bonding to another optical member may be used as an adhesive surface for a release layer or for bonding to another member.

[0063] In another embodiment, the composition may be placed on one surface of each of two optical members in the above-mentioned placing step.

[0064] In the above embodiment, the "one surface" refers to the surface facing the other optical member.

[0065] Furthermore, in another embodiment, in the above-mentioned disposing step, the present composition may also be disposed on another surface located opposite to the one surface.

[0066] In the curing step, the composition is cured at a low temperature range (15 to 80°C), which includes room temperature (25°C). In the embodiments of the present invention, "low temperature" refers to, for example, a temperature range of 15 to 80°C. When the reaction of the composition (including the semi-cured product) is allowed to proceed at a temperature range of 15 to 80°C, the composition may be left standing preferably at around room temperature (a temperature range that can be reached without heating or cooling, particularly including a temperature range of 20 to 25°C), or may be cooled to a temperature 15°C or higher below room temperature, or may be heated to a temperature above room temperature and 80°C or lower.

[0067] In a further embodiment of the present invention, a method for producing a laminate includes a disposing step of disposing the above-mentioned composition on one or both surfaces of at least one of two optical components and laminating the two optical components together via the curable silicone composition; and a curing step of irradiating the composition with high-energy rays through the transparent substrate, followed by leaving or heating the composition to promote a hydrosilylation reaction of the composition and thereby curing the composition.

[0068] In the curing step, the composition is irradiated with high-energy radiation, thereby curing the composition to obtain a cured product. The high-energy radiation is as described above, and is preferably ultraviolet radiation.

[0069] A method for producing a laminate in yet another embodiment of the present invention includes the following steps. Step i): A step of disposing the composition on one or both surfaces of at least one of the two optical members. Step ii): A step of irradiating the composition placed in step i) with high-energy radiation to bring the composition into a non-fluid semi-cured state. Step iii): After step ii), the two optical members are bonded together via a semi-cured composition. Step iv): A step of carrying out a hydrosilylation reaction of the composition in a semi-cured state at a temperature range of 15 to 80°C for the two optical members bonded together in step iii), thereby fully curing the composition.

[0070] In the semi-curing step, the composition is irradiated with high-energy radiation, thereby causing the hydrosilylation reaction to proceed and producing a semi-cured product.

[0071] In the main curing step, the semi-cured product is fully cured by allowing the curing reaction to proceed at a temperature range of 15 to 80° C. This results in a fully cured product, which is obtained by further curing the semi-cured product.

[0072] In a further embodiment of the present invention, a method for producing a laminate includes the following steps. Step i): A step of disposing the composition on one or both surfaces of at least one of two optical members, wherein at least one of the members is a transparent optical member. Step ii): A step of causing the hydrosilylation reaction of the composition placed in step i) to proceed at a temperature range of 15 to 80°C, thereby bringing the composition into a non-flowable semi-cured state. Step iii): After step ii), a step of bonding the two optical members together via the semi-cured composition. Step iv): A step of irradiating the curable silicone composition with high-energy rays through the transparent optical member attached to the two optical members in step iii), and then proceeding with a hydrosilylation reaction of the semi-cured composition at a temperature in the range of 15 to 80°C to fully cure the composition.

[0073] In the semi-curing step, the composition is reacted at a temperature ranging from 15 to 80° C. This results in a semi-cured product in which the hydrosilylation reaction has progressed.

[0074] In the curing step, the semi-cured product is irradiated with high-energy rays, thereby further curing the semi-cured product to obtain a fully cured product.

[0075] The composition has excellent curing properties and forms a cured product that maintains transparency and is resistant to clouding or coloration even when exposed to high temperatures and humidity, making it useful as an adhesive or pressure-sensitive adhesive for use in display devices such as optical displays (including touch panels) and optical semiconductor devices (including Micro LEDs). Furthermore, the composition is not limited to optical displays, and can be used without restriction for laminating or filling transparent members, and can be used, for example, in adhesive layers for solar cells, double-glazed glass (smart glass), optical waveguides, projector lenses (multi-layer lenses, lamination of polarized / optical films), etc.

[0076] In addition, this composition has the general advantage of silicone OCR, namely, that it has low cure shrinkage of the cured product, thereby suppressing display defects such as defects and uneven reflection in displays and optical components.In addition, due to the above-mentioned flexible properties, it has high conformability to adhesive components and develops strong adhesive strength after a certain period of time, effectively suppressing peeling between components, and can be suitably used as an optical adhesive layer for in-vehicle displays with flat or curved display surfaces, head-up displays using the above-mentioned projector lenses, etc. [Example]

[0077] A cured product was obtained from a composition containing the following components: In each average composition formula, Me and Vi represent a methyl group and a vinyl group, respectively.

[0078] [Example 1] Average unit formula: (Me2ViSiO 1 / 2 ) 0.044 (MeSiO 1 / 2 ) 0.411 (SiO 4 / 2 ) 0.545 3.5 parts by weight of vinyl-terminated branched polysiloxane (A-1) represented by the average formula: ViMeSiO(SiMeO)322 89.7 parts by weight of vinyl-terminated linear polysiloxane (A-2) represented by SiMe2Vi, average formula: HMe2SiO(SiMe2O) 10 A composition was prepared containing 6.8 parts by weight of a linear polysiloxane (B-1) represented by SiMe2H, 5 ppm of platinum atoms in a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (C-1), and 20 ppm of platinum atoms in (methylcyclopentadienyl)trimethylplatinum(IV) (D-1). The viscosity of the composition was 1,800 mPa·s. After the composition was prepared, it was left to stand for 10 minutes. The viscosity had increased to 3,200 mPa·s. The composition was then passed through an ozone cut filter and exposed to ultraviolet light from a 2W high-pressure mercury lamp at 365 nm with a dose of 5,000 mJ / cm. 2 When the viscosity was measured immediately after irradiation, it increased to over 30,000 mPa·s, but fluidity was maintained. However, it was confirmed that the material had gelled and become non-fluid 5 minutes after UV irradiation. The hardness of the cured material was measured every 10 minutes using a penetration index, and it stabilized at a constant penetration index of 32 one hour after UV irradiation, confirming that the curing reaction had completed.

[0079] [Example 2] 3.5 parts by weight of A-1, 6.5 parts by weight of A-2, and an average composition formula: ViMe2SiO(SiMe2O) 535 A composition was prepared containing 82.4 parts by weight of vinyl-terminated linear polysiloxane (A-3) represented by SiMe2Vi, 4.6 parts by weight of B-1, 10 ppm of C-1 in terms of platinum atoms, and 20 ppm of D-1 in terms of platinum. The viscosity of the composition was 8,200 mPa·s. After the composition was prepared, it was left to stand for 10 minutes, and the viscosity had increased to 14,000 mPa·s. The composition was then passed through an ozone cut filter and exposed to ultraviolet light from a 2W high-pressure mercury lamp at 365 nm with a dose of 2,500 mJ / cm. 2When the viscosity was measured immediately after irradiation, it increased to over 50,000 mPa·s, but fluidity was maintained. However, it was confirmed that the material had gelled and become non-fluid 10 minutes after UV irradiation. The hardness of the cured material was measured every 10 minutes using a penetration index, and it stabilized at a constant penetration index of 35 one hour after UV irradiation, confirming that the curing reaction had completed.

[0080] [Example 3] Average unit formula: (Me2ViSiO 1 / 2 ) 0.1 (MeSiO 1 / 2 ) 0.4 (SiO 4 / 2 ) 0.5 55.7 parts by weight of vinyl-terminated branched polysiloxane (A-4) represented by the average unit formula: (MeSiO 1 / 2 ) 0.44 (SiO 4 / 2 ) 0.56 13.3 parts by weight of branched polysiloxane (E-1) represented by the average formula: ViMe2SiO(SiMe2O) 160 1.7 parts by weight of vinyl-terminated linear polysiloxane (A-3) represented by SiMe2Vi, average formula: HMe2SiO(SiMe2O) 400 24.6 parts by weight of linear polysiloxane (B-2) represented by SiMe2H, average formula: Me3SiO(SiMe2O) 30 (SiMeHO) 30 A composition containing 4.7 parts by weight of SiMe3 linear polysiloxane (B-3), 0.2 ppm of C-1 as platinum atoms, and 5 ppm of D-1 as platinum atoms was prepared. The viscosity of the composition was 3,500 mPa·s. The composition was heated at 90°C for 30 minutes to obtain a thermoplastic that was not fluid at 25°C but was fluid at 100°C. The obtained thermoplastic did not lose its fluidity at 100°C even after being stored at 25°C for two months. This thermoplastic was prepared by using an ozone-cutting filter and a 2W high-pressure mercury lamp at 365 nm with an ultraviolet irradiation dose of 2,500 mJ / cm. 2 The coating was then heated at 120°C for 30 minutes to obtain a cured product with a Shore A hardness of 80.

[0081] [Example 4] A composition containing 32.2 parts by weight of A-4, 28.5 parts by weight of E-1, 20.7 parts by weight of A-3, 15.7 parts by weight of B-2, 2.9 parts by weight of B-3, 0.1 ppm of C-1 as platinum atoms, and 5 ppm of D-1 as platinum atoms was prepared. The viscosity of the composition was 2,800 mPa·s. The composition was heated at 90°C for 30 minutes to obtain a thermoplastic that was not fluid at 25°C but was fluid at 100°C. The obtained thermoplastic did not lose its fluidity at 100°C even after being stored at 25°C for two months. The thermoplastic was prepared using an ozone-cutting filter and a 2W high-pressure mercury lamp at 365 nm with an ultraviolet irradiation dose of 2500 mJ / cm. 2 The coating was then heated at 120°C for 30 minutes to obtain a cured product with a Shore A hardness of 35.

[0082] [Example 5] Average composition formula: ViMe2SiO(SiMePhO) 36 93.6% by weight of vinyl-terminated linear polysiloxane (A-5) represented by SiMe2Vi, average composition formula: (ViMe2SiO 1 / 2 )0.22(MeXSiO 2 / 2 )0.12(PhSiO 3 / 2 )0.66 (wherein X represents a glycidoxypropyl group), 1.0 wt % of vinyl group-containing polysiloxane (A-6) represented by the molecular formula: PhSi(OSiMeH), 3.9 wt % of linear polysiloxane (B-3) represented by the average composition formula: (HMeSiO 1 / 2 ) 0.6 (PhSiO 3 / 2 ) 0.4 A composition was prepared containing 1.3 wt% of the branched polysiloxane (B-4) represented by the formula: 0.2 wt% of glycidoxypropyltrimethoxysilane, 5 ppm of the C-1 as platinum atoms, and 20 ppm of the D-1 as platinum atoms. The viscosity of the composition was 6,000 mPa·s. The composition was allowed to stand at 25°C for 10 minutes, yielding a thickened material with a viscosity of approximately 12,000 mPa·s. This thickened material was passed through an ozone-cutting filter and exposed to ultraviolet light from a 2W high-pressure mercury lamp at 365 nm with an intensity of 2,500 mJ / cm. 2After irradiating with ultraviolet light at 25°C for 15 minutes, the composition turned into a non-flowable gel, and after 40 minutes at 25°C, a cured product with a needle penetration of 35 was obtained.

[0083] [Comparative Example 1] A composition containing 3.5 parts by weight of A-1, 89.7 parts by weight of A-2, 6.8 parts by weight of B-1, and 60 ppm of platinum atoms in C-1 was prepared. The viscosity of the composition was 1,800 mPa·s. The composition immediately generated heat after preparation, gelled within 1 minute, and became non-fluid. The curing was so rapid that specimens for penetrometer measurement could not be prepared, and the cured product was colored brown.

[0084] Comparative Example 2 A composition containing 3.5 parts by weight of A-1, 89.7 parts by weight of A-2, 6.8 parts by weight of B-1, and 20 ppm of D-1 in terms of platinum atoms was prepared. The viscosity of the composition was 1,800 mPa·s. After the composition was prepared, it was left to stand for 10 minutes, and then the composition with a constant viscosity of 1,800 mPas was passed through an ozone cut filter and exposed to ultraviolet light of 5,000 mJ / cm at 365 nm from a 2 W high-pressure mercury lamp. 2 When the viscosity was measured immediately after irradiation, it had increased to 3,200 mPa·s. As the composition had not gelled even after 1 hour of UV irradiation, it was heated to 100°C, and it was confirmed that it had finally become non-fluid after 30 minutes.

[0085] Comparative Example 3 A composition containing 55.7 parts by weight of A-4, 13.3 parts by weight of E-1, 1.7 parts by weight of A-3, 24.6 parts by weight of B-2, 4.7 parts by weight of B-, and 2 ppm of C-1 (as platinum atoms) was prepared. The viscosity of the composition was 3,500 mPa·s. The composition was heated at 90°C for 30 minutes, yielding a cured product with a Shore A hardness of 80. To obtain a softer cured product, the composition was heated at 50°C for 30 minutes, yielding a cured product with a Shore A hardness of 40. However, the resulting cured product did not exhibit high-temperature fluidity, and the cured product gradually increased in hardness over time, reaching a Shore A hardness of 75 after two weeks at 25°C.

[0086] Comparative Example 4 A composition containing 32.2 parts by weight of A-4, 28.5 parts by weight of E-1, 20.7 parts by weight of A-3, 15.7 parts by weight of B-2, 2.9 parts by weight of B-3, 0.1 ppm of C-1 as platinum atoms, and 5 ppm of D-1 as platinum atoms was prepared. The viscosity of the composition was 2,800 mPa·s. The composition was heated at 90°C for 30 minutes, but no change was observed in the composition.

[0087] Comparative Example 5 A composition containing 94.0 parts by weight of A-2, 4.1 parts by weight of B-2, 1.4 parts by weight of B-3, and 5 ppm of platinum atoms in C-1 was prepared. The viscosity of the composition was 2,100 mPa·s. The composition gelled after 30 minutes at 25°C.

[0088] Comparative Example 6 A composition containing 93.6 wt% of A-5, 1.0 wt% of A-6, 3.9 wt% of B-3, 1.3 wt% of B-4, 0.2 wt% of glycidoxypropyltrimethoxysilane, and 5 ppm of platinum atoms of C-1 was prepared. The viscosity of the composition was 6,000 mPa·s. The composition was left to stand at 25°C for 10 minutes, yielding a thickened material with a viscosity of approximately 12,000 mPa·s. This thickened material was passed through an ozone cut filter and exposed to ultraviolet light from a 2W high-pressure mercury lamp at 365 nm with an irradiation dose of 2,500 mJ / cm. 2 After 60 minutes at 25°C after exposure to ultraviolet light, the composition finally turned into a non-flowable gel, but even after 2 hours at 25°C, the needle penetration continued to decrease, indicating that the curing reaction was not complete. [Industrial Applicability]

[0089] The composition of the present invention has a sufficient pot life at room temperature and can be cured at low temperatures by irradiation with high-energy rays, and is therefore suitable as an adhesive or pressure-sensitive adhesive between layers of image display devices.

Claims

1. A method for producing a laminate, comprising the following steps: Process i): (A) a compound containing at least one aliphatic unsaturated monovalent hydrocarbon group in one molecule; (B) A compound containing at least two hydrogen atoms bonded to silicon atoms in one molecule. (C) a first hydrosilylation catalyst that exhibits activity in the composition without exposure to high-energy radiation; and (D) a second hydrosilylation catalyst that is inactive in the absence of high-energy radiation but becomes active in the composition upon exposure to high-energy radiation; and The component (A) is represented by the general formula: R 6 3 SiO(R 6 2 SiO) m1 SiR 6 3 (wherein each R 6 is independently an unsubstituted or halogen-substituted monovalent hydrocarbon group, at least two R 6 s in one molecule are alkenyl groups, and at least 30 mol % of all R 6 s are aryl groups; and m1 is an integer in the range of 5 to 1,000), The component (B) is represented by the following average unit formula (3): (HR 4 2 SiO 1 / 2 ) e (R 4 3 SiO 1 / 2 ) f (HR 4 SiO 2 / 2 ) g (R 4 2 SiO 2 / 2 ) h (HSiO 3 / 2 ) i (R 4 SiO 3 / 2 ) j (SiO 4 / 2 ) k (R 5 O 1 / 2 ) l (3) (In the formula, R 4 is a group selected from a monovalent hydrocarbon group having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, a hydroxyl group, and an alkoxy group; R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and e, f, g, h, i, j, k, and l are numbers that satisfy the following conditions: e+f+g+h+i+j+k=1, 0≦l≦0.1, 0.01≦e+g+i≦0.2, 0.01≦e≦0.6, 0.01≦g≦0.6, 0≦i≦0.4, 0.01≦e+f≦0.8, 0.01≦g+h≦0.8, 0≦i+j≦0.6.) and a step of disposing a composition of this type in an amount such that the silicon-bonded hydrogen atoms in component (A) are in the range of 0.5 to 2 moles per mole of total alkenyl groups in component (A) on one or both surfaces of at least one of the two optical components. Step ii): A step of irradiating the composition placed in step i) with high-energy radiation to bring the composition into a non-fluid semi-cured state. Step iii): After step ii), the two optical members are bonded together via the semi-cured curable silicone composition. Step iv): A step of carrying out a hydrosilylation reaction of the composition in a semi-cured state at a temperature in the range of 15 to 80°C to fully cure the composition, while the two optical members bonded together in step iii) are being bonded together.

2. A method for producing a laminate, comprising the following steps: Process i): (A) a compound containing at least one aliphatic unsaturated monovalent hydrocarbon group in one molecule; (B) A compound containing at least two hydrogen atoms bonded to silicon atoms in one molecule. (C) a first hydrosilylation catalyst that exhibits activity in the composition without exposure to high-energy radiation; and (D) a second hydrosilylation catalyst that is inactive in the absence of high-energy radiation but becomes active in the composition upon exposure to high-energy radiation; and The component (A) is represented by the general formula: R 6 3 SiO(R 6 2 SiO) m1 SiR 6 3 (wherein each R 6 is independently an unsubstituted or halogen-substituted monovalent hydrocarbon group, at least two R 6 s in one molecule are alkenyl groups, and at least 30 mol % of all R 6 s are aryl groups; and m1 is an integer in the range of 5 to 1,000), The component (B) is represented by the following average unit formula (3): (HR 4 2 SiO 1 / 2 ) e (R 4 3 SiO 1 / 2 ) f (HR 4 SiO 2 / 2 ) g (R 4 2 SiO 2 / 2 ) h (HSiO 3 / 2 ) i (R 4 SiO 3 / 2 ) j (SiO 4 / 2 ) k (R 5 O 1 / 2 ) l (3) (In the formula, R 4 is a group selected from a monovalent hydrocarbon group having 1 to 12 carbon atoms and no aliphatic unsaturated bonds, a hydroxyl group, and an alkoxy group; R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and e, f, g, h, i, j, k, and l are numbers that satisfy the following conditions: e+f+g+h+i+j+k=1, 0≦l≦0.1, 0.01≦e+g+i≦0.2, 0.01≦e≦0.6, 0.01≦g≦0.6, 0≦i≦0.4, 0.01≦e+f≦0.8, 0.01≦g+h≦0.8, 0≦i+j≦0.6.) and a step of disposing a composition of this type on one or both surfaces of at least one of two optical components, the composition being an organohydrogenpolysiloxane represented by the formula: Step ii): A step of causing the hydrosilylation reaction of the composition placed in step i) to proceed at a temperature in the range of 15 to 80°C, thereby bringing the composition into a non-flowable semi-cured state. Step iii): After step ii), the two optical members are bonded together via the semi-cured curable silicone composition. Step iv): A step of irradiating the curable silicone composition with high-energy rays through the transparent optical member attached to the two optical members in step iii), and then proceeding with a hydrosilylation reaction of the semi-cured composition at a temperature in the range of 15 to 80°C, thereby fully curing the composition.

3. The method for producing a laminate according to claim 1 or 2, wherein the laminate is an optical display.