Two-component curable organopolysiloxane composition

Abstract

To provide a two-component curable organopolysiloxane composition that excels in both quick curability and depth curability, and enables curing at room temperature as well as curing by ultraviolet rays.SOLUTION: A two-component curable organopolysiloxane composition includes: a first agent including (A) a linear diorganopolysiloxane with its molecular chain ends capped with hydroxyl groups bonded to silicon atoms, (B) a vinyltri(alkenoxy)silane and / or a partial hydrolysate thereof, and (C) a photopolymerization initiator; and a second agent including (D) a mercapto group-containing organosiloxane, which contains at least two mercapto groups in one molecule, (E) a primary amine compound, and (F) a curing catalyst for moisture curing.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a two-component curable organopolysiloxane composition that has good fast-curing and deep-section curing properties and exhibits both room-temperature curing and ultraviolet curing properties, and to an elastomer molded product (cured silicone rubber) obtained by curing the two-component curable organopolysiloxane composition. [Background technology]

[0002] Various types of UV-curable silicone compositions are known. Among UV-curable silicone compositions, those that use radical polymerization are characterized by their high reactivity, resulting in a fast reaction rate and short curing time. On the other hand, the radicals have a very short lifespan and are easily deactivated by oxygen, etc., which can significantly reduce the curing property of the composition surface that comes into contact with air. In particular, when using a UV lamp with an LED as a light source, the reduction in the surface curing property of UV-curable silicone compositions is significant. Furthermore, UV-curable silicone compositions do not cure in areas that are not exposed to UV light or are blocked.

[0003] In order to solve the problems of known curable silicone compositions as described above, curable organopolysiloxane compositions have been developed that have both room temperature curing and ultraviolet curing properties.

[0004] Japanese Patent Laid-Open Publication No. 60-231761 (Patent Document 1) proposes the use of a hydroxy-terminated organopolysiloxane, a silane having a vinyl group and a hydrolyzable group, and a mercapto group-containing organosiloxane. Japanese Patent No. 2639286 (Patent Document 2) proposes the use of a hydroxy-terminated organopolysiloxane and a (meth)acrylic-functional alkoxysilane. However, while these compositions can cure areas not exposed to UV light by condensation curing, a certain amount of time is required for deep curing, and they are not fast-curing. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 60-231761 [Patent Document 2] Patent No. 2639286 Summary of the Invention [Problem to be solved by the invention]

[0006] Therefore, an object of the present invention is to provide a two-component curable organopolysiloxane composition that has good fast curing properties, deep curing properties, and properties that can be cured at both room temperature and by ultraviolet light. [Means for solving the problem]

[0007] As a result of extensive research, the present inventors have discovered that by using a hydroxy-terminated organopolysiloxane, a silane having a vinyl group and a hydrolyzable group, and a mercapto group-containing organosiloxane, and by further allowing a primary amine compound to be present in the system, water is generated during the condensation reaction, resulting in a curable organopolysiloxane composition that is fast-curing, has good deep curing properties, and is both room-temperature curable and ultraviolet-curable, and has thus completed the present invention.

[0008] That is, the present invention provides the following two-component curable organopolysiloxane composition, a sealant, coating agent, or adhesive containing the composition, and a molded product (cured silicone rubber product) made from the cured product of the composition.

[0009] [1] (A) a linear diorganopolysiloxane having both molecular chain terminals blocked with hydroxyl groups bonded to silicon atoms: 100 parts by mass, (B) the following general formula (1) [ka] (In the formula, R 1 is a substituted or unsubstituted monovalent hydrocarbon group, and R 2 and R3 are each a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, and R 1 and R 2 may be bonded to form an alicyclic ring having a C=C double bond in the above formula together with the carbon atom to which they are attached. 0.5 to 30 parts by mass of a vinyltri(alkenoxy)silane and / or a partial hydrolyzate thereof represented by the formula: (C) Photopolymerization initiator: 0.01 to 20 parts by mass A first agent containing (D) a mercapto group-containing organosiloxane having at least two mercapto groups per molecule: an amount such that the amount of mercapto groups in component (D) is 0.01 to 100 moles per mole of vinyl groups in component (B); (E) a primary amine compound: 0.1 to 20 parts by mass, and (F) Moisture-curing catalyst: 0.01 to 10 parts by mass and a second part containing the above-mentioned compound. [2] The component (D) is represented by the following general formula (2): [ka] (In formula (2), R 4 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and multiple R 4 may be the same or different, and m is an integer of 1 to 20. [1] The two-component curable organopolysiloxane composition according to [1], wherein the organopolysiloxane is a linear or branched organopolysiloxane having at least two groups represented by the following formula (I) in each molecule, and whose main chain is composed of repeating diorganosiloxane units. [3] The two-component curable organopolysiloxane composition according to [1], further comprising (G) a silane coupling agent other than a primary aminosilane in a proportion of 0.1 to 10 parts by mass per 100 parts by mass of component (A) in the first and / or second parts. [4] The two-component curable organopolysiloxane composition according to [1], further comprising (H) a filler that does not inhibit the ultraviolet curing reaction in a proportion of 1 to 500 parts by mass per 100 parts by mass of component (A) in the first and / or second parts. [5] The two-component curable organopolysiloxane composition according to [1], which cures to a depth of 3 mm or more immediately after exposure to ultraviolet light and has a depth of cure of 27 mm in 7 hours. [6] A sealing agent, coating agent, or adhesive comprising the two-component curable organopolysiloxane composition according to any one of [1] to [5]. [7] A molded article comprising a cured product of the two-component curable organopolysiloxane composition according to any one of [1] to [5]. [Effects of the Invention]

[0010] The two-component curable organopolysiloxane composition of the present invention has excellent fast curing and deep curing properties, and is useful as a sealant, adhesive, coating agent, or potting agent. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be described in detail below.

[0012] [Component (A)] Component (A) of the two-component curable organopolysiloxane composition of the present invention is a linear diorganopolysiloxane whose molecular chain is terminally blocked with silicon-bonded hydroxyl groups (silanol groups), and serves as the base polymer in the composition of the present invention. This organopolysiloxane is preferably liquid at room temperature (23°C ± 15°C), and is particularly preferably one represented by the following general formula (3): [ka] (In formula (3), R 5are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 10 carbon atoms, and multiple R 5 may be the same or different, and n is an integer of 10 or more.

[0013] In formula (3), R 5 is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, such as alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, and decyl; cycloalkyl groups such as cyclohexyl; alkenyl groups such as vinyl, allyl, propenyl, and isopropenyl; aryl groups such as phenyl and tolyl; and groups in which the hydrogen atoms of these groups are partially substituted with halogen atoms, such as 3,3,3-trifluoropropyl. Among these, methyl and phenyl groups are particularly preferred. When multiple R in formula (3) 5 may be the same group or different groups.

[0014] Furthermore, n in formula (3) is an integer of 10 or greater, and is an integer that provides a viscosity of the diorganopolysiloxane at 25° C. that is preferably in the range of 25 to 500,000 mPa·s, and more preferably in the range of 500 to 100,000 mPa·s. In the present invention, viscosity is a value measured at 25° C. using, for example, a rotational viscometer (e.g., BL type, BH type, BS type, cone-plate type, rheometer, etc.) (the same applies hereinafter). In the above formula (3), the bifunctional diorganosiloxane unit ((R 5 )2SiO 2 / 2 The value of n, which indicates the number of repetitions (or degree of polymerization) of the formula (III), is an integer of 10 or more, preferably an integer of 10 to 2,000, more preferably an integer of 50 to 1,200, and even more preferably an integer of about 100 to 1,000. In the present invention, the degree of polymerization is a value determined as the polystyrene-equivalent number-average degree of polymerization (or number-average molecular weight) in gel permeation chromatography (GPC) analysis using toluene or the like as a developing solvent. The component (A) may be one type or a mixture of two or more types.

[0015] [(B) Component] The curing agent (crosslinking agent) of component (B) is a vinyltri(alkenoxy)silane having one silicon-bonded vinyl group and three silicon-bonded alkenoxy groups per molecule, and / or a partial hydrolysis condensate thereof, as represented by the following general formula (1): (i.e., an organosiloxane oligomer having an average of three or more residual hydrolyzable groups per molecule, obtained by partial hydrolysis and condensation of a vinyltri(alkenoxy)silane compound): [ka] (In the formula, R 1 is a substituted or unsubstituted monovalent hydrocarbon group, and R 2 and R 3 are each a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, and R 1 and R 2 may be bonded to form an alicyclic ring having a C=C double bond in the above formula together with the carbon atom to which they are attached.

[0016] In the above formula, R 1 is a substituted or unsubstituted monovalent hydrocarbon group, preferably having 1 to 10 carbon atoms. Examples of monovalent hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, butyl, and cyclohexyl, alkenyl groups such as vinyl and allyl, aryl groups such as phenyl, aralkyl groups such as benzyl, and halogen-substituted alkyl groups such as 3,3,3-trifluoropropyl. Particularly preferred are methyl, ethyl, vinyl, and phenyl groups. When multiple R in formula (1) 1 may be the same group or different groups.

[0017] R 2 and R 3are each a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, and the monovalent hydrocarbon group preferably has 1 to 10 carbon atoms, and examples of such monovalent hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, and isobutyl. 2 The R groups may be the same or different groups. 3 may be the same group or different groups. Also, R 1 and R 2 may be bonded to form an alicyclic ring having a C=C double bond in the above formula together with the carbon atom to which they are bonded. The multiple alicyclic rings in formula (1) may be the same group or different groups.

[0018] The amount of component (B) blended is 0.5 to 30 parts by mass, preferably 1 to 8 parts by mass, per 100 parts by mass of component (A). If the amount is less than 0.5 parts by mass, sufficient crosslinking (curing) is not achieved, and it may be difficult to obtain a composition that gives a cured product (silicone rubber) with the desired rubber elasticity. If the amount exceeds 30 parts by mass, the deep curing of the composition may be impaired, resulting in reduced workability.

[0019] [(C) component] The photopolymerization initiator (C) can be any of those conventionally used in UV-curable organopolysiloxane compositions. Specific examples include acetophenone, propiophenone, benzophenone, fluorene, benzaldehyde, anthraquinone, triphenylamine, carbazole, 3-methylacetophenone, 4-methylacetophenone, 3-pentylacetophenone, 4-methoxyacetophenone, 3-bromoacetophenone, 4-allylacetophenone, p-diacetylbenzene, 3-methoxybenzophenone, 4-methylbenzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 2,2-diethoxyacetophenone, 4-chloro-4'-benzylbenzophenone, 3-chloroxanthone, 3,9-dichloroxanthone, 3-chloro-8-nonylxanthone, and benzylacetophenone. Examples of such compounds include benzoin, benzoin methyl ether, benzoin butyl ether, bis(4-dimethylaminophenyl) ketone, benzyl methoxy ketal, 2-chlorothioxanthone, diethylacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1[4-(methylthio)phenyl]-2-morpholino-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone, 1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propan-1-one, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and cyclohexyl phenyl ketone.

[0020] The amount of component (C) blended is 0.01 to 20 parts by mass, and preferably 0.1 to 10 parts by mass, per 100 parts by mass of component (A). If the amount of component (C) blended is less than 0.01 part by mass, the effect is small, but if it exceeds 20 parts by mass, the decomposition residue of component (C) will have a significant effect on the obtained cured product, which may result in poor physical properties. The component (C) may be used alone or in combination of two or more.

[0021] In the first agent, the contents of the components (A), (B) and (C) are preferably from 20 to 100% by mass, more preferably from 30 to 100% by mass.

[0022] [(D) component] The curing agent (crosslinking agent) of component (D) is a mercapto-containing organosiloxane having at least two mercapto groups per molecule, preferably 2 to 20, and more preferably 4 to 10, mercapto groups per molecule.

[0023] The component (D) is represented by the following general formula (2): [ka] (In formula (2), R 4 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and multiple R 4 may be the same or different, and m is an integer of 1 to 20. Particularly preferred is a linear or branched organopolysiloxane having at least two groups represented by the following formula in one molecule, and having a main chain consisting of repeating diorganosiloxane units.

[0024] Component (D) is a component that acts as a crosslinking agent for the composition, and has at least two groups represented by the above general formula (2) in one molecule, preferably 2 to 20 groups, and more preferably 4 to 10 groups.

[0025] In the general formula (2), R 4Examples of the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl groups; cyclopentyl and cyclohexyl groups; Examples of suitable groups include alkyl groups; alkenyl groups such as vinyl, allyl, butenyl, pentenyl, and hexenyl; aryl groups such as phenyl, tolyl, xylyl, and α- and β-naphthyl; aralkyl groups such as benzyl, 2-phenylethyl, and 3-phenylpropyl; and groups in which some or all of the hydrogen atoms in these groups have been substituted with halogen atoms such as F, Cl, and Br, or cyano groups, such as 3-chloropropyl, 3,3,3-trifluoropropyl, and 2-cyanoethyl. Among these, methyl, ethyl, and phenyl groups are preferred, with methyl being particularly preferred from the standpoints of availability, productivity, and cost. m is an integer of 1 to 20, preferably an integer of 1 to 6. Multiple R in Eq. (2) 4 may be the same group or different groups.

[0026] Component (D) may be, for example, a linear, branched, partially branched, or dendrimeric organopolysiloxane, preferably a linear or partially branched organopolysiloxane, and more preferably a linear organopolysiloxane having a main chain consisting of a repeating structure of divalent siloxane units (i.e., (triorganosiloxy)(mercaptoalkyl)siloxane units) represented by the partial structural formula of general formula (2) above, and both molecular chain terminals blocked with hydroxyl groups (silanol groups) bonded to silicon atoms (side-chain mercaptoalkyl-modified linear organopolysiloxanes), but is not limited thereto. Component (D) may also be a single polymer having these molecular structures, a copolymer consisting of these molecular structures, or a mixture of these polymers.

[0027] The amount of component (D) to be added is such that the number of mercapto groups in component (D) is 0.01 to 100 moles, and preferably 0.5 to 20 moles, per mole of vinyl groups in component (B).If the number of mercapto groups in component (D) per mole of vinyl groups in component (B) is less than 0.1 moles, sufficient curability may not be obtained, while if it is more than 100 moles, a cured product with the desired physical properties may not be obtained. The component (D) may be used alone or in combination of two or more.

[0028] [(E) component] Examples of the primary amine compound of component (E) include alkylamines, cycloalkylamines, diamines, alkenylamines, arylamines, amino-modified silanes, amino-modified siloxanes, and partial hydrolysates thereof.

[0029] Examples of alkylamines include methylamine, ethylamine, propylamine, butylamine, and hexylamine. Examples of cycloalkylamines include cyclopentylamine and cyclohexylamine. Examples of diamines include ethylenediamine and hexamethylenediamine. Examples of alkenylamines include vinylamine and allylamine. The arylamines include, for example, aniline. Examples of amino-modified silanes include 3-aminopropylmethyldimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyldimethylmethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-2-aminoethyl-3-aminopropyltrimethoxysilane, and N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane. Examples of amino-modified siloxanes include γ-aminopropylpentamethyldisiloxane, γ-aminopropylheptamethyltetracyclosiloxane, 1,2-di(γ-aminopropyl)tetramethyldisiloxane, 1-γ-aminopropyl-2,3-isopropylhexamethyltetracyclosiloxane, α,ω-trimethylsiloxypoly(γ-aminopropylmethyl)siloxane, and α,ω-trimethylsiloxypoly[N-β-(aminoethyl)-γ-aminopropylmethyl]siloxane.

[0030] Among these primary amine compounds, more preferred are amino-modified silanes or amino-modified siloxanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, α,ω-trimethylsiloxypoly(γ-aminopropylmethyl)siloxane, and N-2-aminoethyl-3-aminopropyltrimethoxysilane.

[0031] The amount of component (E) blended is 0.1 to 20 parts by mass, preferably 2 to 10 parts by mass, per 100 parts by mass of diorganopolysiloxane (A). If the amount of primary amine compound (E) is too small, the composition will not be able to achieve sufficient deep curing. If the amount is too large, component (E) will leach out of the cured product, causing environmental pollution and other problems, and the resulting cured product may have reduced tensile strength. The component (E) may be used alone or in combination of two or more.

[0032] [Component (F)] The moisture-curing catalyst (F) acts as a condensation reaction catalyst and may be the same or different, and may be used alone or as a mixture of two or more.

[0033] Specific examples of component (F) include tin catalysts such as tin dioctoate, dimethyltin diversatate, dibutyldimethoxytin, dibutyltin diacetate, dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin dibenzyl maleate, dioctyltin dilaurate, and tin chelate; strongly basic compounds such as guanidine and DBU (1,8-diazabicyclo[5.4.0]-7-undecene) and alkoxysilanes containing residues of these strongly basic compounds; and titanate esters or titanium chelate compounds such as tetraisopropoxytitanium, tetra-n-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, dipropoxybis(acetylacetonate)titanium, and titanium isopropoxyoctylene glycol. Specific examples of alkoxysilanes containing residues of strongly basic compounds include tetramethylguanidylpropyltrimethoxysilane.

[0034] The amount of component (F) blended is 0.01 to 10 parts by mass, and preferably 0.02 to 5 parts by mass, per 100 parts by mass of the diorganopolysiloxane of component (A). If it is less than 0.01 part by mass, sufficient curing properties will not be obtained, and if it exceeds 10 parts by mass, the durability of the composition may decrease.

[0035] In the second agent, the contents of the components (D), (E) and (F) are preferably from 20 to 100% by mass, more preferably from 30 to 100% by mass.

[0036] [(G) component] When adhesiveness is required, the composition of the present invention can be blended with a silane coupling agent other than (G) primary aminosilane (i.e., other than the above-mentioned (E) component) as an adhesion-imparting component. Known silane coupling agents are preferably used. Particularly preferred are those having an alkoxysilyl group or two or less alkenoxysilyl groups per molecule as the hydrolyzable group. Examples include vinyltris(β-methoxyethoxy)silane, methacryloxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, glycidoxypropyltrimethoxysilane, glycidoxypropylmethyldiethoxysilane, mercaptopropyltrimethoxysilane, glycidoxypropyltriisopropenoxysilane, and glycidoxypropylmethyldiisopropenoxysilane. Among these, methacryloxypropyltrimethoxysilane is particularly preferred.

[0037] When the silane coupling agent (G) is added, the amount added is preferably 0.1 to 10 parts by mass, and particularly preferably 0.2 to 5 parts by mass, per 100 parts by mass of the diorganopolysiloxane (A). If the amount is less than 0.1 part by mass, sufficient adhesion may not be obtained, and if the amount is more than 10 parts by mass, the cost may be disadvantageous. The component (G) may be used alone or in combination of two or more.

[0038] [(H) component] The composition of the present invention may further contain (H) a filler that does not inhibit the UV curing reaction, which acts as a reinforcing agent or extender in the composition of the present invention. Examples of the filler of component (H) include reinforcing fillers such as fumed silica, wet silica, precipitated silica, and calcium carbonate. Preferred are fumed silica, precipitated silica, and calcium carbonate. These fillers may be untreated or may be surface-treated with a known treatment agent.

[0039] When the filler (H) is added to the composition of the present invention, the amount added is preferably 1 to 500 parts by mass, and particularly preferably 2 to 250 parts by mass, per 100 parts by mass of the diorganopolysiloxane (A). If the amount is less than 1 part by mass, the effect of the addition may be insufficient, while if it exceeds 500 parts by mass, the dischargeability and workability of the composition of the present invention may be reduced. The component (H) may be used alone or in combination of two or more.

[0040] Other components may be added to the composition of the present invention as needed, provided that the effects of the present invention are not impaired. Examples of other components include polyether as a thixotropy improver, non-reactive dimethyl silicone oil as a plasticizer, isoparaffin, and a network polysiloxane consisting of trimethylsiloxy units and SiO2 units as a crosslink density improver.

[0041] Manufacturing method The two-component curable organopolysiloxane composition of the present invention is prepared by separately preparing a first part containing components (A), (B), and (C), and optionally components (G), (H), and other components, and a second part containing components (D), (E), and (F), and optionally components (G), (H), and other components, and mixing the first and second parts together using a static or dynamic mixer or the like before use.

[0042] Curing method The two-component curable organopolysiloxane composition of the present invention is cured by irradiating the composition with ultraviolet light. The ultraviolet light having a wavelength of 250 to 450 nm, and particularly 250 to 380 nm, is effective, and the irradiation dose of the ultraviolet light is 1,000 to 10,000 mJ / cm. 2 , especially 2,000 to 5,000 mJ / cm 2 The curing temperature may be room temperature, usually 25°C ± 10°C.

[0043] Furthermore, in the two-component curable organopolysiloxane composition of the present invention, component (B) reacts as a crosslinking agent in the hydrolysis reaction to generate a carbonyl compound, and the generated carbonyl compound reacts with component (E) to generate water. This water promotes the hydrolysis of component (B) and accelerates the crosslinking reaction, resulting in not only improved curability but also rapid crosslinking in shadowed and deep areas of the composition that are not exposed to ultraviolet light.

[0044] The curable organopolysiloxane composition of the present invention can be suitably used as a sealant, adhesive, coating agent, or potting agent. In particular, the room-temperature-curable organopolysiloxane composition of the present invention can be suitably used in applications that involve shadowed or deep areas that are not exposed to ultraviolet light. [Example]

[0045] The present invention will be described in detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. In the following specific examples, "parts" means "parts by mass," and the viscosity is the value measured with a rotational viscometer at 25°C.

[0046] [Example 1] Composition 1-1 was prepared by mixing 100 parts of a dimethylpolysiloxane (corresponding to R5 = CH3, n = 230 in formula (3)) with a viscosity of 700 mPa·s and both ends blocked with hydroxyl groups, 3.7 parts of vinyltri(isopropenoxy)silane, 6.5 parts of fumed silica, and 1.0 part of diethoxyacetophenone until uniform, as the first agent. As a second agent, 3.3 parts of 3-aminopropyltriethoxysilane, 1.1 parts N,N,N',N'-guanidylpropyltrimethoxysilane, 11 parts of γ-mercaptopropyl group-containing organopolysiloxane (manufactured by Shin-Etsu Chemical Co., Ltd.) represented by the following formula (4): [ka] The above ingredients were mixed until uniform to prepare Composition 1-2. The entire amount of composition 1-1 and the entire amount of composition 1-2 were mixed together to obtain the composition of Example 1.

[0047] [Example 2] Composition 2-2 was prepared in the same manner as in Example 1, except that 3.3 parts of N-2-aminoethyl-3-aminopropyltrimethoxysilane was used instead of 3.3 parts of 3-aminopropyltriethoxysilane described in Composition 1-2 of Example 1. The entire amount of composition 1-1 and the entire amount of composition 2-2 were mixed together to obtain the composition of Example 2.

[0048] [Comparative Example 1] Composition 3-2 was prepared in the same manner as in Example 1, except that 3.3 parts of 3-aminopropyltriethoxysilane described in composition 1-2 of Example 1 was not used. The entire amount of composition 1-1 and the entire amount of composition 3-2 were mixed together to obtain a composition of Comparative Example 1.

[0049] Comparative Example 2 Composition 4-2 was prepared in the same manner as in Example 1, except that 11 parts of the 3-mercaptopropyl group-containing organopolysiloxane represented by the above formula (4) (manufactured by Shin-Etsu Chemical Co., Ltd.) described in composition 1-2 of Example 1 was not used. The entire amount of composition 1-1 and the entire amount of composition 4-2 were mixed together to obtain a composition of Comparative Example 2.

[0050] Comparative Example 3 Composition 5-1 was prepared in the same manner as in Example 1, except that 2.2 parts of methyltrimethoxysilane was used instead of 3.7 parts of vinyltriisopropenoxysilane in composition 1-1 of Example 1. The entire amount of composition 5-1 and the entire amount of composition 1-2 were mixed together to obtain a composition of Comparative Example 3.

[0051] [Examples 1 to 2, Comparative Examples 1 to 3] The prepared composition was placed in a plastic cup having a depth of 27 mm, and the wall of the cup was covered with aluminum foil so that ultraviolet light was irradiated only from above. The light source used was a UV-LED lamp ultraviolet irradiation device (manufactured by World Engineering Co., Ltd.), and the irradiation dose of ultraviolet light with a wavelength of 365 nm was 4,000 mJ / cm 2 Each composition was irradiated with ultraviolet light and cured so that the cured composition was The thickness of the cured film was checked immediately after UV irradiation and after aging for 7 hours at 23°C and 50% RH. The thickness of the cured film was also checked after aging for 7 hours at 23°C and 50% RH without UV irradiation. The surface curability was also checked 3 minutes after UV irradiation. Surface curability was evaluated as follows: no tackiness on the surface, △, undurable or with bleeding of uncured oil. The results are shown in Tables 1 and 2.

[0052] [Table 1]

[0053] [Table 2]

[0054] Comparison of Examples 1 and 2 with Comparative Examples 1 to 3 demonstrates that the two-component curable organopolysiloxane composition of the present invention is excellent in fast curing and deep curing properties. Furthermore, the two-component curable organopolysiloxane composition of the present invention is formulated from versatile material components and can be produced industrially with advantage.

Claims

1. (A) 100 parts by mass of a linear diorganopolysiloxane whose molecular chain is terminated at both ends with hydroxyl groups bonded to silicon atoms, (B) the following general formula (1): 【Chemistry 1】 (In the formula, R 1 is a substituted or unsubstituted monovalent hydrocarbon group, and R 2 and R 3 are each a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, and R 1 and R 2 may be bonded to form an alicyclic ring having a C═C double bond in the above formula together with the carbon atom to which they are attached. Vinyltri(alkenoxy)silane and / or a partial hydrolyzate thereof: 0.5 to 30 parts by mass, and (C) Photopolymerization initiator: 0.01 to 20 parts by mass A first agent containing (D) the following general formula (2): 【Chemistry 2】 (In formula (2), R 4 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and a plurality of R 4 may be the same or different, and m is an integer of 1 to 20. a mercapto group-containing organosiloxane which is a linear organopolysiloxane having 4 to 10 groups represented by the formula (I) per molecule, whose main chain consists of repeating diorganosiloxane units, and whose molecular chain is terminated at both ends with hydroxyl groups bonded to silicon atoms, in an amount such that the amount of mercapto groups in component (D) is 0.01 to 100 moles per mole of vinyl groups in component (B); (E) a primary amino-modified silane: 2 to 20 parts by mass, and (F) Moisture-curing catalyst: 0.01 to 10 parts by mass and a second part containing the above-mentioned compound.

2. The two-component curable organopolysiloxane composition according to claim 1, further comprising a silane coupling agent, excluding components (G) and (E), in the first and / or second parts in an amount of 0.1 to 10 parts by mass per 100 parts by mass of component (A).

3. The two-component curable organopolysiloxane composition according to claim 1, further comprising (H) a filler that does not inhibit the UV curing reaction in an amount of 1 to 500 parts by mass per 100 parts by mass of component (A) in the first and / or second parts.

4. 2. The two-component curable organopolysiloxane composition according to claim 1, which cures to a depth of at least 3 mm immediately after exposure to ultraviolet light and has a depth of cure of 27 mm in 7 hours.

5. A sealing agent, coating agent, or adhesive comprising the two-component curable organopolysiloxane composition according to any one of claims 1 to 4.

6. A molded article comprising a cured product of the two-component curable organopolysiloxane composition according to any one of claims 1 to 4.

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