Room-temperature-curable resin composition and article

Abstract

The room-temperature-curable resin composition contains an organosilicon compound represented by formula (1) and yields a highly strengthened cured product. (In the formula, R1 independently represent a substituted or unsubstituted monovalent C1-12 hydrocarbon group, excluding aliphatic unsaturated bonds; R2 represents a hydrogen atom or an aliphatic unsaturated monovalent C2-12 hydrocarbon group; R3 independently represent a substituted or unsubstituted monovalent C1-12 hydrocarbon group, excluding aliphatic unsaturated bonds; A represents a divalent C2-8 hydrocarbon group; k represents an integer of 0-2; m represents an integer of 3-6; k+m represents an integer of 3-8; and n represents an integer of 0-100.)

Description

Room temperature curable resin composition and article

[0001] The present invention relates to a room-temperature-curable resin composition that provides a cured product with enhanced strength, in particular a room-temperature-curable resin composition (i.e., a room-temperature-curable organopolysiloxane composition) that contains a curable organopolysiloxane as the main component (base polymer) and an organosilicon compound (a silanol group-containing polyfunctional cyclic organopolysiloxane compound) having a specific molecular structure as a strength-enhancing agent, and that provides an organopolysiloxane elastomer elastic body (a silicone rubber cured product) with improved tensile strength and adhesive strength; and to coating agents, adhesives, and sealants that contain the composition, as well as articles that are coated, bonded, or sealed with a cured product of the composition.

[0002] Conventionally, condensation-curable room-temperature-curable organopolysiloxane compositions and the like have been known as room-temperature-curable resin compositions that undergo a condensation reaction with moisture (humidity) in the air at room temperature (23°C ± 15°C) to crosslink and cure to give an elastomer elastic body (cured rubber product). These room-temperature-curable organopolysiloxane compositions are widely used in construction, transportation, electrical and electronic components, and the like, due to their safety, durability as a rubber, and excellent adhesive properties. In particular, the tensile strength and adhesive strength of the cured product are often considered important, as they have a significant impact on the reliability of the components in which they are used.

[0003] Among room-temperature-curable organopolysiloxane compositions, so-called one-component (single-liquid) room-temperature-curable organopolysiloxane compositions do not require the complicated weighing and mixing of a base polymer, crosslinking agent, catalyst, etc. immediately before use, and are therefore free from the risk of formulation errors. In addition, they generally exhibit excellent adhesion to a wide range of substrates even when a primer is not used, and are therefore widely used as elastic adhesives and coating materials in the electrical and electronics industries and as building sealants.

[0004] Such one-component room-temperature-curable organopolysiloxane compositions are often classified according to the type of compound released from the composition upon contact with moisture in the air, with representative examples including deacetic acid-, deoxime-, deamido-, dehydroxylamine-, deacetone-, and dealcohol-type organopolysiloxane compositions. Among these, for example, deoxime-type organopolysiloxane compositions that cure by releasing oxime are characterized by excellent storage stability and the ability to produce excellent cured coatings in a short period of time, while dealcohol-type organopolysiloxane compositions that cure by releasing alcohol have properties such as low odor, no corrosion of metals such as copper and iron, excellent self-adhesion (adhesion to various substrates after curing when no primer is used), and excellent adhesion durability, and are used in fields that make the most of their respective characteristics.

[0005] However, it is known that one-component room-temperature-curable organopolysiloxane compositions generally produce cured products with low tensile strength and adhesive strength.

[0006] In one-component room-temperature-curable organopolysiloxane compositions, the addition of fillers such as silica or colloidal calcium carbonate has long been known as a method for increasing the tensile strength and adhesive strength of the cured product (Non-Patent Document 1). However, if the amount of filler added is too large, the viscosity of the composition increases significantly, resulting in limitations such as reduced workability during use, and a new method has been sought.

[0007] "Silicone Handbook" by Kunio Ito, Nikkan Kogyo Shimbun, 1990

[0008] The present invention has been made in view of the above circumstances, and has as its object the provision of a room-temperature-curable resin composition (i.e., a room-temperature-curable organopolysiloxane composition), in particular a condensation-curable room-temperature-curable organopolysiloxane composition (a so-called condensation-curable RTV silicone rubber composition), which gives a cured product with increased strength, particularly an organopolysiloxane elastomer elastic body (a silicone rubber cured product) with improved tensile strength and adhesive strength, as well as coating agents, adhesives, and sealants containing said composition, as well as articles coated, bonded, or sealed with a cured product of said composition.

[0009] As a result of intensive research conducted by the present inventors in order to achieve the above object, they have found that by blending an organosilicon compound represented by the following formula (1) as a strength-enhancing agent into a room-temperature-curable resin composition, the tensile strength and adhesive strength of the cured product of the composition can be improved, and have completed the present invention.

[0010] That is, the present invention provides the following room-temperature-curable resin compositions, coating agents, adhesives, sealants, and articles coated, bonded, or sealed with a cured product of the compositions: [1] A room-temperature-curable resin composition containing an organosilicon compound represented by the following formula (1): (In the formula, R 1 are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 12 carbon atoms excluding aliphatic unsaturated bonds, and R 2 is a hydrogen atom or an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, and R 3are independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms excluding aliphatic unsaturated bonds, A is a divalent hydrocarbon group having 2 to 8 carbon atoms, k is an integer of 0 to 2, m is an integer of 3 to 6, k + m is an integer of 3 to 8, and n is an integer of 0 to 100.) [2] The room-temperature-curable resin composition according to [1], which contains a curable organopolysiloxane. [3] The room-temperature-curable resin composition according to [2], which contains the following components (A) to (D): (A) 0.01 to 50 parts by mass of an organosilicon compound represented by the above formula (1), (B) 100 parts by mass of a curable organopolysiloxane, (C) 0.1 to 30 parts by mass of a hydrolyzable organosilane compound and / or a partial hydrolyzed condensate thereof other than components (A) and (B), and (D) 0.01 to 15 parts by mass of a curing catalyst. [4] The room-temperature-curable resin composition according to [3], further comprising at least one selected from the following components (E) to (G) per 100 parts by mass of the component (B): (E) filler: 1 to 1,000 parts by mass, (F) adhesion promoter: 1 to 30 parts by mass, and (G) plasticizer: 1 to 1,000 parts by mass. [5] A coating agent comprising the room-temperature-curable resin composition according to any one of [1] to [4]. [6] An adhesive comprising the room-temperature-curable resin composition according to any one of [1] to [4]. [7] A sealant comprising the room-temperature-curable resin composition according to any one of [1] to [4]. [8] An article having a coating layer comprising a cured product of the room-temperature-curable resin composition according to any one of [1] to [4]. [9] An article bonded and / or sealed with a cured product of the room-temperature-curable resin composition according to any one of [1] to [4].

[0011] In the present invention, the organosilicon compounds defined above are included in the present invention as long as the average structure of the organosilicon compound aggregate is within the above range, even if there are differences in structure between the individual organosilicon compounds.

[0012] According to the present invention, by including an organosilicon compound having a specific molecular structure (a silanol group-containing polyfunctional cyclic organopolysiloxane compound) as a strength-enhancing agent, it is possible to obtain a room-temperature-curable resin composition that gives a cured product with improved tensile strength and adhesive strength.

[0013] The present invention will be described in detail below.

[0014] The room-temperature-curable resin composition of the present invention contains, as a strength-enhancing agent, an organosilicon compound (silanol group-containing polyfunctional cyclic organopolysiloxane compound) of component (A): The room-temperature-curable resin composition of the present invention is particularly a room-temperature-curable organopolysiloxane composition (a so-called condensation-curable RTV silicone rubber composition) containing the organosilicon compound of component (A) and the curable organopolysiloxane of component (B) as the main component (base polymer), and more specifically, a condensation-curable room-temperature-curable organopolysiloxane composition containing the following components (A), (B), (C), and (D), and, optionally, at least one selected from components (E), (F), and (G):

[0015] Component (A) is an organosilicon compound represented by the following formula (1), and is used as a strength increasing agent for room temperature curable resin compositions. (In the formula, R 1 are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 12 carbon atoms excluding aliphatic unsaturated bonds, and R 2 is a hydrogen atom or an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, and R 3 are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 12 carbon atoms excluding aliphatic unsaturated bonds, A is a divalent hydrocarbon group having 2 to 8 carbon atoms, k is an integer of 0 to 2, m is an integer of 3 to 6, k+m is an integer of 3 to 8, and n is an integer of 0 to 100.

[0016] Component (A) is an organosilicon compound (cyclic organopolysiloxane compound) represented by the above formula, and is a silanol group-containing polyfunctional cyclic organopolysiloxane compound having, via a divalent hydrocarbon group (A), diorganohydroxysilyl groups or 3 to 6 (i.e., m) monovalent organosiloxanyl groups having terminal silanol groups (hydroxy groups bonded to silicon atoms) as monovalent substituents (side chains) bonded to silicon atoms constituting the cyclic organopolysiloxane consisting of 3 to 8 (i.e., (k+m)) siloxane units.

[0017] Here, in the formula (1), R 1 Examples of unsubstituted or substituted monovalent hydrocarbon groups having 1 to 12 carbon atoms and excluding aliphatic unsaturated bonds, represented by the formula (I), include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, and dodecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; 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 of these groups have been substituted with halogen atoms such as F, Cl, and Br, or with cyano groups, such as 3-chloropropyl, 3,3,3-trifluoropropyl, and 2-cyanoethyl. Among these, R 1 As the alkyl group, a lower alkyl group such as a methyl group, an ethyl group, an isopropyl group, or a butyl group, or an aryl group such as a phenyl group is preferred, with a methyl group or a phenyl group being particularly preferred.

[0018] In the formula (1), R 2 Among the hydrogen atoms or aliphatic unsaturated monovalent hydrocarbon groups having 2 to 12 carbon atoms represented by the formula (I), examples of the aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms include alkenyl groups such as vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, pentenyl group, hexenyl group, and cyclohexenyl group; and alkynyl groups such as ethynyl group (acetylenyl group), ethynylmethyl group, and the like. 2 As the alkyl group, a hydrogen atom or an alkenyl group such as a vinyl group or an allyl group is preferred, with a hydrogen atom and a vinyl group being particularly preferred.

[0019] In the formula (1), R 3 The unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms excluding an aliphatic unsaturated bond, represented by the above R 1Examples of the alkyl group include the same groups as those exemplified as R, such as alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, and dodecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; 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 of these groups have been substituted with halogen atoms such as F, Cl, and Br, or with cyano groups, such as 3-chloropropyl, 3,3,3-trifluoropropyl, and 2-cyanoethyl. 3 As the alkyl group, a lower alkyl group such as a methyl group, an ethyl group, an isopropyl group, or a butyl group, or an aryl group such as a phenyl group is preferred, with a methyl group or a phenyl group being particularly preferred.

[0020] In the formula (1), A is a divalent hydrocarbon group such as an alkylene group or an alkenylene group having 2 to 8 carbon atoms, preferably 2 to 4 carbon atoms, and the divalent hydrocarbon group is —(CH) p Preferred are alkylene groups such as - (p represents an integer of 2 to 8, preferably an integer of 2 to 4). Of these, -CH2CH2- and -CH2CH2CH2- are more preferred.

[0021] In the formula (1), k is an integer of 0 to 2, and preferably 0 or 1.

[0022] In the formula (1), m is an integer of 3 to 6, preferably 4 or 5. In the formula (1), k+m is an integer of 3 to 8, preferably 4 to 6.

[0023] In the formula (1), n ​​is an integer of 0 to 100, preferably an integer of 0 to 20, more preferably an integer of 0 to 10, and even more preferably an integer of 0 to 4.

[0024] <Method for Producing Organosilicon Compound> The organosilicon compound of the present invention represented by the formula (1) can be produced by a method including the following steps [I] or [II]: [I] A compound represented by the following formula (2) (In the formula, R 3 , n is the same as above) and an organohydrogensilane or organohydrogenpolysiloxane represented by the following formula (3): (In the formula, R 1 , k, m, k+m are the same as above, and R 2’ [II] A step of subjecting a cyclic organopolysiloxane represented by the following formula (4): (In the formula, R 3 , n is the same as above, and R 2’ is an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, and an organosilane or organopolysiloxane represented by the following formula (5): (In the formula, R 1 , k, m, and k+m are the same as above), in the presence of a platinum compound-containing catalyst, subjecting a cyclic organohydrogenpolysiloxane represented by the following formula (I) to a hydrosilylation addition reaction.

[0025] Specifically, an organohydrogensilane (where n=0 in formula (2)) having a silanol group (a hydroxyl group bonded to a silicon atom) and a silicon-bonded hydrogen atom (a hydrosilyl group represented by SiH) in the molecule, as represented by the above formula (2), or an organohydrogenpolysiloxane (where n=1 to 100 in formula (2)) having a silanol group at one end of the molecular chain and a silicon-bonded hydrogen atom at the other end of the molecular chain, is used, and an aliphatic unsaturated monovalent hydrocarbon group (R 2’ ) in the presence of a platinum compound-containing catalyst, or by subjecting a cyclic organopolysiloxane having a silanol group and an aliphatic unsaturated monovalent hydrocarbon group (R 2’) (when n=0 in formula (4)) or an organosilane having an aliphatic unsaturated monovalent hydrocarbon group (R 2’ ), and a silanol group at the other end of the molecular chain (where n = 1 to 100 in formula (4)), and a cyclic organohydrogenpolysiloxane having silicon-bonded hydrogen atoms represented by formula (5) are subjected to a hydrosilylation addition reaction in the presence of a platinum compound-containing catalyst to form an aliphatic unsaturated monovalent hydrocarbon group (R 2’ ) to form a carbon-silicon bond (i.e., the silicon-bonded hydrogen atom (SiH group) in the above formula (2) and the aliphatic unsaturated monovalent hydrocarbon group (R 2’ ), or an addition reaction between a silicon-bonded hydrogen atom (SiH group) in the above formula (5) and an aliphatic unsaturated monovalent hydrocarbon group (R 2’ ) to form a divalent hydrocarbon group such as an alkylene group and / or an alkenylene group represented by A in formula (1), thereby producing an organosilicon compound represented by formula (1).

[0026] Here, in the above formulas (3) and (4), R 2’ The aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms represented by the formula (1) is 2 Among these, the same groups as those exemplified as the aliphatic unsaturated monovalent hydrocarbon groups having 2 to 12 carbon atoms can be mentioned. 2’ As the alkyl group, a vinyl group, an alkenyl group such as an allyl group, etc. is preferred, and a vinyl group is particularly preferred.

[0027] Specific examples of the organohydrogensilane or organohydrogenpolysiloxane represented by the above formula (2) include those shown below. (wherein n is the same as above.)

[0028] Specific examples of the cyclic organopolysiloxane represented by the above formula (3) include those shown below.

[0029] Specific examples of the organosilane or organopolysiloxane represented by the above formula (4) include those shown below. (wherein n is the same as above.)

[0030] Specific examples of the cyclic organohydrogenpolysiloxane represented by the above formula (5) include those shown below.

[0031] Regarding the reaction ratio of the organohydrogensilane or organohydrogenpolysiloxane represented by formula (2) with the cyclic organopolysiloxane represented by formula (3), in consideration of suppressing by-products during the hydrosilylation addition reaction and improving the storage stability and properties of the resulting organosilicon compound, the ratio of aliphatic unsaturated monovalent hydrocarbon groups such as alkenyl groups and alkynyl groups in the cyclic organopolysiloxane represented by formula (3) is preferably 0.5 to 1.5 mol, and more preferably 0.7 to 1.4 mol, per 1 mol of hydrosilyl groups (SiH groups) in the organohydrogensilane or organohydrogenpolysiloxane represented by formula (2).

[0032] Furthermore, in consideration of suppressing by-products during the hydrosilylation addition reaction and improving the storage stability and properties of the resulting organosilicon compound, the reaction ratio between the organosilane or organopolysiloxane represented by formula (4) and the cyclic organohydrogenpolysiloxane represented by formula (5) is preferably such that 0.5 to 1.5 mol, and more preferably 0.7 to 1.4 mol, of aliphatic unsaturated monovalent hydrocarbon groups such as alkenyl groups and alkynyl groups in the organosilane or organopolysiloxane represented by formula (4) per 1 mol of hydrosilyl groups (SiH groups) in the cyclic organohydrogenpolysiloxane represented by formula (5).

[0033] The platinum compound-containing catalyst used in the hydrosilylation addition reaction is not particularly limited, and specific examples include chloroplatinic acid, an alcohol solution of chloroplatinic acid, a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, tetrakistriphenylphosphine platinum, dichlorobistriphenylphosphine platinum, dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum, dichlorocyclooctadiene platinum, supported catalysts such as platinum-carbon, platinum-alumina, and platinum-silica. Of these, a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex is preferred from the viewpoint of regioselectivity of the hydrosilylation addition reaction.

[0034] The amount of platinum compound-containing catalyst used is not particularly limited, but from the viewpoint of reactivity and productivity, it is preferable that the amount of platinum atoms contained is 1×10 per 1 mol of organosilane compound or organopolysiloxane compound having an aliphatic unsaturated monovalent hydrocarbon group such as an alkenyl group or alkynyl group represented by the above formula (3) or (4). -7 ~1 x 10 -2 The amount is preferably 1×10 -7 ~1 x 10 -3 It is more preferable that the amount is 100 mol.

[0035] A co-catalyst may be used to improve the reactivity of the hydrosilylation addition reaction. While any co-catalyst generally used in hydrosilylation addition reactions can be used, in the present invention, ammonium salts of inorganic acids, acid amide compounds, and carboxylic acids are preferred.

[0036] Specific examples of ammonium salts of inorganic acids include ammonium chloride, ammonium sulfate, ammonium amidosulfate, ammonium nitrate, monoammonium dihydrogen phosphate, diammonium hydrogen phosphate, triammonium phosphate, ammonium diphosphite, ammonium carbonate, ammonium hydrogen carbonate, ammonium sulfide, ammonium borate, ammonium fluoroborate, etc. Among these, ammonium carbonate and ammonium hydrogen carbonate are preferred.

[0037] Specific examples of the acid amide compound include formamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, propionamide, acrylamide, malonamide, succinamide, maleamide, fumaramide, benzamide, phthalamide, palmitic acid amide, and stearic acid amide. Among these, formamide and stearic acid amide are preferred, and formamide is more preferred.

[0038] Specific examples of carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, methoxyacetic acid, pentanoic acid, caproic acid, heptanoic acid, octanoic acid, lactic acid, glycolic acid, trifluoroacetic acid, maleic acid, fumaric acid, succinic acid, tartaric acid, and oxalic acid. Among these, formic acid, acetic acid, lactic acid, maleic acid, fumaric acid, succinic acid, and trifluoroacetic acid are preferred, and acetic acid and trifluoroacetic acid are more preferred.

[0039] The amount of the co-catalyst used is not particularly limited, but from the viewpoints of the reactivity and regioselectivity of the hydrosilylation addition reaction, cost, etc., it is preferred that the amount of the co-catalyst used be 1×10 per 1 mol of the organosilane compound or organopolysiloxane compound having an aliphatic unsaturated monovalent hydrocarbon group such as an alkenyl group or alkynyl group represented by the above formula (3) or (4). -5 ~1 x 10 -1 mol is preferred, and 1×10 -4 ~5 x 10 -1 mol is more preferred.

[0040] The hydrosilylation addition reaction proceeds in the absence of a solvent, but can also be carried out in the presence of a solvent. Specific examples of solvents that can be used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene; ether solvents such as diethyl ether, tetrahydrofuran, and dioxane; ester solvents such as ethyl acetate and butyl acetate; aprotic polar solvents such as N,N-dimethylformamide; and chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents can be used alone or in combination.

[0041] The amount of solvent used is not particularly limited, but from the viewpoint of productivity, such as production efficiency, it is preferably 0 to 1,000 parts by mass, and more preferably 0 to 300 parts by mass, per 100 parts by mass of the total of the organosilane compound or organopolysiloxane compound having an aliphatic unsaturated monovalent hydrocarbon group, such as an alkenyl group or alkynyl group, represented by formula (3) or (4) above, and the organosilane compound or organopolysiloxane compound having a silicon-bonded hydrogen atom, represented by formula (2) or (5) above.

[0042] The reaction temperature in the hydrosilylation addition reaction is not particularly limited, and the reaction can be carried out from room temperature (23°C ± 15°C) under heating, with room temperature (23°C ± 15°C) to 200°C being preferred. To obtain a moderate reaction rate, the reaction is more preferably carried out under heating, and when the reaction is carried out under heating, the reaction temperature is more preferably 40 to 110°C, and even more preferably 40 to 90°C. The reaction time is also not particularly limited, and is preferably 1 to 60 hours, more preferably 1 to 30 hours, and even more preferably 1 to 20 hours.

[0043] Examples of the compound represented by formula (1) obtained in this manner include, but are not limited to, those represented by the following formulas: (In the formula, k is an integer of 0 to 2, m is an integer of 3 to 6, k+m is an integer of 3 to 8, and n is an integer of 0 to 100.)

[0044] Specific examples of the compound represented by formula (1) obtained in this manner include, but are not limited to, the following compounds:

[0045] The amount of component (A) blended is usually preferably 0.01 to 50 parts by mass, and more preferably 0.1 to 10 parts by mass, per 100 parts by mass of the main agent (base polymer), particularly component (B) described below. If the blending amount is less than 0.01 part by mass, the resulting cured product may not be strong enough (the effect of improving tensile strength and shear adhesive strength to the substrate), whereas if the blending amount exceeds 50 parts by mass, the resulting cured product may be too hard, which may be economically disadvantageous.

[0046] Component (B) is a curable organopolysiloxane, which serves as the main component (base polymer) of the room-temperature-curable resin composition of the present invention and has at least one silicon-bonded hydroxyl group (silanol group) or hydrolyzable silyl group in the molecule. Specific examples of such organopolysiloxanes include diorganopolysiloxanes represented by the following general formulas (6) to (9) in which both molecular chain terminals or one molecular chain terminal are blocked with silicon-bonded hydroxyl groups (silanol groups) or hydrolyzable silyl groups. Among these, diorganopolysiloxanes in which both molecular chain terminals or one molecular chain terminal are blocked with silicon-bonded hydroxyl groups are particularly preferred. (In the formula, R 4 are independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms, X is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, Y is independently a hydrolyzable group, a is 0 or 1, and p is a number that gives the diorganopolysiloxane a viscosity at 23°C of 100 to 1,000,000 mPa·s.

[0047] In the above formulas (6) to (9), R 4 The unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms represented by the formula (I) is preferably one excluding aliphatic unsaturated bonds, and examples thereof include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, and dodecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; 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 of these groups have been substituted with halogen atoms such as F, Cl, and Br, or with cyano groups, such as 3-chloropropyl, 3,3,3-trifluoropropyl, and 2-cyanoethyl. Among these, examples of R 4As the alkyl group, a lower alkyl group such as a methyl group, an ethyl group, an isopropyl group, or a butyl group, or an aryl group such as a phenyl group is preferred, with a methyl group being particularly preferred.

[0048] In the above formulas (6) to (9), X is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, and is —(CHCH) q - or -(CH=CH) q Preferably, it is one represented by - (q represents 1 to 4). Among these, an oxygen atom, -CH2CH2-, and -CH=CH- are particularly preferred.

[0049] In the above formula (8) or (9), Y represents a hydrolyzable group, and examples thereof include alkoxy groups such as methoxy, ethoxy, and propoxy; alkoxyalkoxy groups such as methoxyethoxy, ethoxyethoxy, and methoxypropoxy; acyloxy groups such as acetoxy, octanoyloxy, and benzoyloxy; alkenyloxy groups such as vinyloxy, isopropenoyl, and 1-ethyl-2-methylvinyloxy; ketoxime groups such as dimethylketoxime, methylethylketoxime, and diethylketoxime; amino groups such as dimethylamino, diethylamino, butylamino, and cyclohexylamino; aminoxy groups such as dimethylaminooxy and diethylaminooxy; and amide groups such as N-methylacetamide, N-ethylacetamide, and N-methylbenzamide. Among these, alkoxy groups are particularly preferred.

[0050] The organopolysiloxane of component (B) preferably has a viscosity at 23°C of 100 to 1,000,000 mPa·s, more preferably 300 to 500,000 mPa·s, particularly preferably 500 to 100,000 mPa·s, and especially preferably 1,000 to 80,000 mPa·s. If the organopolysiloxane has a viscosity of 100 mPa·s or more, it is possible to obtain a coating film with excellent physical and mechanical strength. If the viscosity is 1,000,000 mPa·s or less, the viscosity of the room-temperature-curable resin composition does not become too high, which reduces workability during use. In the present invention, the viscosity is a value measured using a rotational viscometer (e.g., BL type, BH type, BS type, cone-plate type, etc.).

[0051] In the above formulas (6) to (9), the difunctional diorganosiloxane unit ((SiR 4 2O 2 / 2 ))) (or the degree of polymerization) is usually an integer of 50 or more, preferably an integer of 100 to 2,000, more preferably an integer of 150 to 1,000, and particularly preferably an integer of 200 to 800.

[0052] In the present invention, the degree of polymerization (or molecular weight) can be determined, for example, as a polystyrene-equivalent number-average degree of polymerization (or number-average molecular weight) determined by gel permeation chromatography (GPC) analysis using toluene, tetrahydrofuran (THF), or the like as a developing solvent.

[0053] The organopolysiloxane of component (B) may be used alone or in combination of two or more types differing in structure or molecular weight.

[0054] Component (C) is a hydrolyzable organosilane compound and / or its partial hydrolysis condensate other than the above-mentioned components (A) and (B), and acts as a curing agent (crosslinking agent) in the room-temperature-curable resin composition of the present invention. Examples of hydrolyzable groups in the hydrolyzable organosilane compound of component (C) include ketoxime groups, alkoxy groups, acyloxy groups, alkenyloxy groups, acetamide groups, amino groups, and aminoxy groups, with ketoxime groups, alkoxy groups, and alkenyloxy groups being preferred. In the present invention, the term "partial hydrolysis condensate" refers to an organosiloxane oligomer having at least two, preferably three or more, residual hydrolyzable groups in the molecule, which is produced by partial hydrolysis and condensation of hydrolyzable silane compounds. Furthermore, component (C) is different from component (A) described above and also different from component (F) described below.

[0055] Such a hydrolyzable organosilane compound is preferably a compound represented by the following general formula (10): 5 b SiY' 4-b (10) (wherein, R 5 are each independently an unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms, Y' is independently a hydrolyzable group, and b is an integer of 0 to 3, preferably an integer of 1 to 3, and more preferably 1 or 2.

[0056] In the above formula (10), R 5 Examples of unsubstituted monovalent hydrocarbon groups having 1 to 12 carbon atoms include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl, allyl, butenyl, pentenyl, and hexenyl; aryl groups such as phenyl, tolyl, xylyl, and α- and β-naphthyl; and aralkyl groups such as benzyl, 2-phenylethyl, and 3-phenylpropyl. Among these, alkyl groups such as methyl and ethyl, and alkenyl groups such as vinyl are preferred, with methyl and vinyl being particularly preferred.

[0057] In addition, in the above formula (10), examples of the hydrolyzable group for Y' include alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and tert-butoxy, alkenyloxy groups such as vinyloxy, allyloxy, propenoxy, isopropenoxy, and (cyclopent-1-en-1-yl)oxy, ketoxime groups such as dimethylketoxime, diethylketoxime, methylethylketoxime, and methylisobutylketoxime, acyloxy groups such as acetoxy, acetamide groups such as N-methylacetamide and N-ethylacetamide, hydroxyl groups such as diethylhydroxyl, and amino groups such as butylamino. Among these, ketoxime, alkoxy, acetoxy, and alkenyloxy groups are preferred, and ketoxime, alkoxy, and alkenyloxy groups are more preferred.

[0058] Specific examples of component (C) include ketoxime group-containing silanes such as methyltris(methylethylketoxime)silane, vinyltris(methylethylketoxime)silane, methyltris(methylisobutylketoxime)silane, and vinyltris(methylisobutylketoxime)silane; alkoxysilanes such as methyltrimethoxysilane, dimethyldimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, and methyltriethoxysilane; silyl enol ethers such as methyltriisopropenoxysilane, vinyltriisopropenoxysilane, phenyltriisopropenoxysilane, methyltris[(cyclopent-1-en-1-yl)oxy]silane, vinyltris[(cyclopent-1-en-1-yl)oxy]silane, and phenyltris[(cyclopent-1-en-1-yl)oxy]silane; and partial hydrolysis condensates of these silanes. These can be used alone or in combination of two or more.

[0059] The amount of component (C) blended is usually preferably 0.1 to 30 parts by mass, more preferably 0.2 to 20 parts by mass, and even more preferably 0.5 to 15 parts by mass, per 100 parts by mass of component (B). If the blending amount is less than 0.1 part by mass, the composition may have poor curability, while if it exceeds 30 parts by mass, the resulting cured product may be too hard, which may be economically disadvantageous.

[0060] Component (D) is a curing catalyst (condensation reaction catalyst) used to cure this composition. Examples of curing catalysts include alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctoate, and dioctyltin dilaurate; titanate esters or titanium chelate compounds such as tetraisopropoxytitanium, tetra-n-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, dipropoxybis(acetylacetonato)titanium, and titanium isopropoxyoctylene glycol; organometallic compounds such as zinc naphthenate, zinc stearate, zinc-2-ethyloctoate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, alkoxyaluminum compounds, and aluminum chelate compounds; amine compounds and salts thereof such as hexylamine and dodecylamine phosphate; and benzophenone. Examples of the silanes include quaternary ammonium salts such as methyltriethylammonium acetate, lower fatty acid salts of alkali metals such as potassium acetate, sodium acetate, and lithium oxalate, dialkylhydroxylamines such as dimethylhydroxylamine and diethylhydroxylamine, silanes or siloxanes containing a guanidyl group such as tetramethylguanidylpropyltrimethoxysilane, tetramethylguanidylpropylmethyldimethoxysilane, and tetramethylguanidylpropyltris(trimethylsiloxy)silane, and silanes or siloxanes containing a phosphazene base such as N,N,N',N',N'',N''-hexamethyl-N'''-[3-(trimethoxysilyl)propyl]-phosphorimidic triamide, but these are not limited to one type and may be used as a mixture of two or more types.

[0061] The amount of the curing catalyst (D) blended is preferably 0.01 to 15 parts by mass, and particularly preferably 0.01 to 5 parts by mass, per 100 parts by mass of the component (B). If the amount of component (D) is too small, a sufficient curing rate may not be obtained, whereas if the amount is too large, the curing rate may be too fast and sufficient workability may not be ensured.

[0062] Component (E) is a filler that is blended as needed and is used to impart sufficient mechanical strength to a cured product formed from this composition. Known fillers can be used for this filler, and examples thereof include one or more of surface-treated or untreated (i.e., hydrophobic or hydrophilic) dry silica such as fused silica, calcined silica, fumed silica, and silica aerogel; wet silica such as precipitated silica and sol-gel silica; silica-based fine powders such as diatomaceous earth; metal oxides such as iron oxide, zinc oxide, and titanium oxide; or those whose surfaces have been hydrophobized with a silane compound or the like; calcium carbonates such as colloidal calcium carbonate and heavy calcium carbonate; metal carbonates such as magnesium carbonate and zinc carbonate; inorganic fillers such as asbestos, glass wool, carbon black, and finely divided mica; and synthetic resin powders such as polystyrene, polyvinyl chloride, and polypropylene.

[0063] When component (E) is blended, the blending amount is preferably 1 to 1,000 parts by mass, more preferably 1 to 400 parts by mass, and particularly preferably 5 to 200 parts by mass per 100 parts by mass of component (B). If the amount is less than 1 part by mass, the cured product obtained from this composition tends to lack sufficient mechanical strength, while if more than 1,000 parts by mass is used, not only does the viscosity of the composition increase, making workability difficult, but the rubber strength after curing also tends to decrease, making it difficult to obtain rubber elasticity.

[0064] Component (F) is an adhesion promoter that is blended as needed. Examples of this adhesion promoter include silane coupling agents (e.g., hydrolyzable organosilane compounds containing a monovalent hydrocarbon group (so-called carbon functional group) having a functional group such as a (meth)acryloxy functional group, an epoxy functional group, an amino functional group (excluding guanidyl groups), a mercapto functional group, an isocyanate functional group, or a halogen atom, as well as partial hydrolysis condensates thereof). In particular, it is preferred to blend one or more types selected from aminosilanes such as 3-aminopropyltriethoxysilane and 3-2-(aminoethylamino)propyltrimethoxysilane [also known as N-2-(aminoethyl)-3-aminopropyltrimethoxysilane], epoxysilanes such as γ-glycidoxypropyltrimethoxysilane and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and isocyanate silanes such as γ-isocyanatopropyltriethoxysilane.

[0065] When component (F) is added, the amount of the adhesion promoter added is preferably 0.1 to 30 parts by mass, and particularly preferably 0.2 to 10 parts by mass, per 100 parts by mass of component (B). If the amount of adhesion promoter is too small, the resulting cured product may have poor adhesion, whereas if the amount is too large, the composition may not cure properly.

[0066] Component (G) is a plasticizer that is added as needed, and it can adjust the viscosity of the composition to be easy to handle during application without impairing the mechanical properties or flame retardancy of the cured product formed from this composition.

[0067] Examples of the plasticizer used in the room temperature curable resin composition of the present invention include dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), diheptyl phthalate (DHP), dioctyl phthalate (DOP), diisononyl phthalate (DINP), diisodecyl phthalate (DIDP), ditridecyl phthalate (DTDP), butyl benzyl phthalate (BBP), dicyclohexyl phthalate (DCHP), tetrahydrofuran (THF ... Trihydrophthalic acid ester, dioctyl adipate (DOA), diisononyl adipate (DINA), diisodecyl adipate (DIDA), di-n-alkyl adipate, dibutyl diglycol adipate (BXA), bis(2-ethylhexyl) azelaate (DOZ), dibutyl sebacate (DBS), dioctyl sebacate (DOS), dibutyl maleate (DBM), di-2-ethylhexyl maleate (DOM), phthalic acid ester Examples of suitable solvents include dibutyl malate (DBF), tricresyl phosphate (TCP), triethyl phosphate (TEP), tributyl phosphate (TBP), tris(2-ethylhexyl)phosphate (TOP), tri(chloroethyl)phosphate (TCEP), trisdichloropropyl phosphate (CPP), tributoxyethyl phosphate (TBXP), tris(β-chloropropyl)phosphate (TMCPP), triphenyl phosphate (TPP), octyldiphenyl phosphate (ODP), acetyltriethyl citrate, and acetyltributyl citrate; trimellitic acid-based plasticizers, polyester-based plasticizers, chlorinated paraffin, and stearic acid-based plasticizers; silicone oils (non-functional organopolysiloxanes) such as dimethylpolysiloxane; and petroleum-based high-boiling solvents such as polyoxypropylene glycol, paraffin, naphthene, and isoparaffin. These may be used alone or in combination of two or more. Among these, silicone oil is particularly preferred.

[0068] As the silicone oil (non-functional organopolysiloxane), an organopolysiloxane represented by the following general formula (11) can be preferably used. (In the formula, R 6are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 20 carbon atoms that do not contain aliphatic unsaturated bonds, and r is a number that gives the organopolysiloxane a viscosity of 1.5 to 1,000,000 mPa·s at 23°C.

[0069] In the above formula (11), R 6 are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 20 carbon atoms and not containing an aliphatic unsaturated bond. Specific examples include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl; aryl groups such as phenyl, tolyl, xylyl, and naphthyl; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl; and groups in which some or all of the hydrogen atoms of these groups have been substituted with halogen atoms such as F, Cl, or Br, such as chloromethyl, chloropropyl, bromoethyl, and trifluoropropyl.

[0070] The organopolysiloxane represented by formula (11) preferably has a viscosity of 1.5 to 1,000,000 mPa·s, and more preferably 10 to 100,000 mPa·s, at 23° C. If the organopolysiloxane has a viscosity of less than 1.5 mPa·s, the mechanical properties and flame retardancy of the resulting cured product may be impaired, while if it exceeds 1,000,000 mPa·s, the viscosity may become difficult to handle during application, resulting in poor workability.

[0071] In the organopolysiloxane represented by the above formula (11), the value of r, which indicates the number of repeating diorganosiloxane units (degree of polymerization), is usually a number from 3 to 3,000, preferably from 5 to 2,000, and more preferably from 10 to 1,000.

[0072] When component (G) is added, the amount added is preferably 1 to 1,000 parts by mass, more preferably 2 to 500 parts by mass, and even more preferably 5 to 200 parts by mass, per 100 parts by mass of component (B). When the amount of component (G) is within the above range, the viscosity can be adjusted to be easy to handle in application without impairing the mechanical properties and flame retardancy of the room-temperature-curable resin composition of the present invention, which is preferable.

[0073] [Other Components] The room-temperature-curable resin composition of the present invention may further contain, as additives other than components (A) to (G), known additives such as pigments, dyes, antioxidants, antistatic agents, antioxidants such as iron oxide, antimony oxide, flame retardants such as chlorinated paraffins, etc. Furthermore, polyethers as thixotropy improvers, mildew inhibitors, and antibacterial agents may also be added, provided that the object of the present invention is not impaired.

[0074] The room-temperature-curable resin composition of the present invention may contain an organic solvent, if necessary. Examples of the organic solvent include aliphatic hydrocarbon compounds such as n-hexane, n-heptane, isooctane, and isododecane; aromatic hydrocarbon compounds such as toluene and xylene; linear siloxanes such as hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and 2-(trimethylsiloxy)-1,1,1,2,3,3,3-heptamethyltrisiloxane; and cyclic siloxanes such as octamethylcyclopentasiloxane and decamethylcyclopentasiloxane. The amount of the organic solvent may be adjusted as appropriate within a range that does not impair the effects of the present invention.

[0075] The room-temperature-curable resin composition of the present invention can be prepared, for example, by uniformly mixing the above-mentioned components (A) to (D), and, if necessary, components (E) to (G), and other components, in a conventional manner. The obtained room-temperature-curable resin composition cures, for example, by leaving it at room temperature (23°C ± 10°C). The molding method, curing conditions, and the like can be determined by known methods and conditions depending on the type of composition. For example, the composition can be cured by leaving it in the atmosphere under conditions of 23°C / 50% RH for several hours to several days (e.g., 6 hours to 7 days).

[0076] The room-temperature-curable resin composition of the present invention can be cured in a short time and has sufficient adhesive strength after curing.

[0077] The cured product of the room-temperature-curable resin composition of the present invention exhibits good flexibility and rubber elasticity, and is therefore useful as a coating agent, adhesive, or sealant (for example, a construction sealant, etc.). The method of using the room-temperature-curable resin composition of the present invention as a coating agent, adhesive, or sealant may be any conventionally known method, and is not particularly limited.

[0078] Examples of articles having a coating layer made of a cured product of the room-temperature-curable resin composition of the present invention include articles made of glass, various resins, various metals, etc., but the material and shape of the substrate are not particularly limited.

[0079] The strength of the cured product of the room temperature curable resin composition of the present invention refers to hardness, tensile strength and tensile shear adhesive strength, and can be measured according to the provisions of JIS K-6249.

[0080] The present invention will be described in more detail below with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited to the following examples. In the following examples, the molecular weight refers to the number average molecular weight in terms of polystyrene measured by GPC using toluene as the developing solvent. The properties in the examples are values ​​at 23°C. "Parts" means "parts by mass." The viscosity is a value measured using a rotational viscometer at 23°C.

[0081] Synthesis of Organosilicon Compounds [Synthesis Example 1] Synthesis of Organosilicon Compound 1 Into a 500 mL separable flask equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 34.4 g (0.1 mol, alkenyl group amount: 0.4 mol) of 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane and 0.15 g of a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum atomic weight: 6.8 × 10 -6mol) and 50 g of toluene were placed in a flask and heated to 80°C. 119.5 g (0.4 mol, SiH group amount: 0.4 mol) of an organopolysiloxane having a silicon-bonded hydrogen atom (SiH group) at one molecular chain end and a silanol group (a hydroxyl group bonded to a silicon atom) at the other end, represented by the following formula (12), was added dropwise thereto, and the mixture was heated and stirred at 80°C for 3 hours. The reaction was terminated when gas chromatography measurement confirmed that the peak derived from the organopolysiloxane having a silicon-bonded hydrogen atom at one molecular chain end of the raw material had completely disappeared. After completion of the reaction, the mixture was subjected to vacuum distillation (120°C, 5 mmHg) for 2 hours and filtered, yielding 151.4 g of organosilicon compound 1 (number average molecular weight: 1,571) represented by the following formula (13):

[0082] Synthesis Example 2 Synthesis of Organosilicon Compound 2 Into a 500 mL separable flask equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 40.8 g (0.4 mol, alkenyl group amount: 0.4 mol) of vinyl(dimethyl)hydroxysilane represented by the following formula (14), 0.15 g of a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum atomic weight: 6.8×10 -6 A flask containing 24.1 g of 1,3,5,7-tetramethyl-1,3,5,7-tetrahydrogencyclotetrasiloxane (0.1 mol, SiH group amount: 0.4 mol) and 50 g of toluene was heated to 80°C. 24.1 g of 1,3,5,7-tetramethyl-1,3,5,7-tetrahydrogencyclotetrasiloxane (0.1 mol, SiH group amount: 0.4 mol) was added dropwise thereto, and the mixture was heated and stirred at 80°C for 3 hours. The reaction was terminated when gas chromatography measurement confirmed that the peaks derived from the raw material organopolysiloxane having alkenyl groups had completely disappeared. After the reaction was completed, evaporation under reduced pressure (120°C, 5 mmHg) was carried out for 2 hours, and filtration was carried out to obtain 64.3 g of organosilicon compound 2 (number average molecular weight: 651) represented by the following formula (15).

[0083] Example 1 A linear dimethylpolysiloxane (R 4= methyl group, X = oxygen atom, p = approximately 620), 15 parts of a linear dimethylpolysiloxane (non-functional dimethylpolysiloxane) having a viscosity of 100 mPa s and terminated at both molecular chain ends with trimethylsilyl groups as a plasticizer, 3 parts of organosilicon compound 1, and 10 parts of fumed silica were added and mixed under reduced pressure for 30 minutes. Next, 5 parts of methyltris(methylethylketoxime)silane, 3 parts of vinyltris(methylethylketoxime)silane, 0.05 parts of dioctyltin dilaurate, and 1 part of 3-aminopropyltriethoxysilane (KBE-903, manufactured by Shin-Etsu Chemical Co., Ltd.) as an adhesion promoter were added, and the mixture was again mixed under reduced pressure until uniform, thereby preparing Composition 1.

[0084] Example 2 Composition 2 was prepared in the same manner as in Example 1, except that 2 parts of organosilicon compound 2 was added instead of organosilicon compound 1.

[0085] Comparative Example 1 Composition 3 was prepared in the same manner as in Example 1, except that organosilicon compound 1 was not added.

[0086] Example 3 A linear dimethylpolysiloxane (R 4 = methyl group, X = oxygen atom, p = approximately 620), 15 parts of a linear dimethylpolysiloxane (non-functional dimethylpolysiloxane) having a viscosity of 100 mPa s and terminated at both molecular chain ends with trimethylsilyl groups as a plasticizer, 3 parts of organosilicon compound 1, 50 parts of colloidal calcium carbonate, and 50 parts of heavy calcium carbonate were added and mixed under reduced pressure for 30 minutes. Next, 10 parts of vinyltriisopropenoxysilane, 0.5 parts of tetramethylguanidylpropyltrimethoxysilane, and 0.5 parts of N-2-(aminoethyl)-3-aminopropyltrimethoxysilane (KBM-603, manufactured by Shin-Etsu Chemical Co., Ltd.) as an adhesion promoter were added, and the mixture was mixed again under reduced pressure until uniform, thereby preparing Composition 4.

[0087] Example 4 Composition 5 was prepared in the same manner as in Example 3, except that 2 parts of organosilicon compound 2 was added instead of organosilicon compound 1.

[0088] Comparative Example 2 Composition 6 was prepared in the same manner as in Example 3, except that organosilicon compound 1 was not added.

[0089] (Tests) [Sheet Properties] Immediately after preparation, each of the room-temperature-curable resin compositions prepared in Examples 1 to 4 and Comparative Examples 1 and 2 was molded into a 2 mm thick sheet, exposed to an atmosphere of 23°C and 50% RH, and then the sheet was left to stand in the same atmosphere for 7 days. The physical properties (hardness, tensile strength) of the resulting cured product were measured in accordance with JIS K-6249. The hardness was measured using a Durometer A hardness tester according to JIS K-6249. The results are shown in Tables 1 and 2.

[0090] [Shear Adhesion Test] Each of the room-temperature curable resin compositions (Compositions 1 to 6) prepared in Examples 1 to 4 and Comparative Examples 1 and 2 immediately after preparation was sandwiched between two aluminum plates (adherends) each having a width of 25 mm and a length of 100 mm, and aged at 23°C and 50% RH for 7 days to obtain an adhesive area of ​​2.5 mm. 2 Shear bond strength was measured in accordance with JIS K-6249. The results are shown in Tables 1 and 2.

[0091]

[0092]

[0093] From the results in Tables 1 and 2, it is clear that the cured products (silicone rubber cured products) of the room-temperature-curable resin compositions of the present invention produced in Examples 1 to 4 are elastomer cured products (rubber elastomers) with excellent mechanical properties (rubber hardness, tensile strength, and shear bond strength), and in particular have higher tensile strength and shear bond strength than the cured products of the room-temperature-curable resin compositions produced in the corresponding Comparative Examples 1 and 2.

Claims

1. A room temperature curable resin composition comprising an organosilicon compound represented by the following formula (1): (In the formula, R 1 are independently unsubstituted or substituted monovalent hydrocarbon groups having 1 to 12 carbon atoms excluding aliphatic unsaturated bonds, R 2 is a hydrogen atom or an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, R 3 are independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms excluding aliphatic unsaturated bonds, A is a divalent hydrocarbon group having 2 to 8 carbon atoms, k is an integer from 0 to 2, m is an integer from 3 to 6, k+m is an integer from 3 to 8, and n is an integer from 0 to 100.

2. The room temperature curable resin composition according to claim 1, which contains a curable organopolysiloxane.

3. The room temperature curable resin composition according to claim 2, comprising the following components (A) to (D): (A) 0.01 to 50 parts by mass of an organosilicon compound represented by the above formula (1), (B) 100 parts by mass of a curable organopolysiloxane, (C) 0.1 to 30 parts by mass of a hydrolyzable organosilane compound and / or a partial hydrolysis condensate thereof other than components (A) and (B), and (D) 0.01 to 15 parts by mass of a curing catalyst.

4. The room-temperature curable resin composition according to claim 3, further comprising at least one selected from the following components (E) to (G) per 100 parts by mass of the component (B): (E) filler: 1 to 1,000 parts by mass, (F) adhesion promoter: 1 to 30 parts by mass, and (G) plasticizer: 1 to 1,000 parts by mass.

5. A coating agent comprising the room temperature curable resin composition according to any one of claims 1 to 4.

6. An adhesive comprising the room temperature curable resin composition according to any one of claims 1 to 4.

7. A sealant comprising the room temperature curable resin composition according to any one of claims 1 to 4.

8. An article having a coating layer made of a cured product of the room temperature curable resin composition according to any one of claims 1 to 4.

9. An article bonded and / or sealed with a cured product of the room temperature curable resin composition according to any one of claims 1 to 4.

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