Chain extender, room temperature curable resin composition using the same, coating agent, adhesive and sealant, and article

Abstract

Provided is a room temperature curable resin composition containing a hydrolyzable organosilane compound as a chain length extender, which is quickly rubberized and develops moderate elongation due to the effect of extending chain length. The room temperature curable resin composition contains (A) 100 parts by mass of a silicone polymer having a molecular chain of which both ends are sealed with a silanol group or a hydrolyzable silyl group, (B) 0.001-30 parts by mass of an organoxymethylene group-containing organosilane compound represented by formula (1) (in the formula, R1, R2, and R3 are each independently an unsubstituted or substituted C1-10 alkyl group, or an unsubstituted or substituted C6-10 aryl group), (C) 0.001-30 parts by mass of a crosslinking agent other than component (B), and (D) 0.001-20 parts by mass of a curing catalyst.

Description

[Technical Field]

[0001] The present invention relates to a room-temperature-curable resin composition (room-temperature-curable organopolysiloxane composition) containing, as a base, a silicone polymer (organopolysiloxane) having, at both molecular chain terminals, silicon-bonded hydroxyl groups (i.e., silanol groups) or hydrolyzable silyl groups as silicon-containing groups capable of crosslinking by forming siloxane bonds (hereinafter also referred to as "reactive silicon-containing groups"). The present invention also relates to coating agents, adhesives, and sealants made from the room-temperature-curable resin composition, as well as to articles coated, bonded, or sealed with a cured product of the room-temperature-curable resin composition. [Background technology]

[0002] Reactive silicon-containing groups, particularly hydrolyzable silyl groups, have the property of undergoing hydrolytic condensation in the presence of water, and therefore polymers having such reactive silicon-containing groups can be used in room-temperature-curable compositions that undergo crosslinking and curing at room temperature (23°C ± 15°C) in the presence of atmospheric water or moisture.

[0003] Among these polymers, those whose main chains have a silicon-containing structure (particularly, preferably a linear organopolysiloxane structure) are generally known as silicone polymers. Room-temperature vulcanizable (RTV) organopolysiloxane compositions using these as the base silicone polymer are liquid at room temperature (23°C ± 15°C) and characteristically turn into silicone rubber elastomers upon curing (crosslinking reaction). Taking advantage of this characteristic, they are widely used in coatings, adhesives, construction sealants, and the like. These room-temperature vulcanizable (RTV) resin compositions use hydrolyzable organosilane compounds and their partial hydrolyzed condensates as crosslinking agents and stabilizers. In particular, bifunctional hydrolyzable organosilane compounds, which have two hydrolyzable groups per molecule, are called chain extenders among crosslinkers, and by extending the chain length of the base silicone polymer, they impart appropriate elongation to sealants and cured RTV rubber products.

[0004] Various types of room temperature vulcanizable (RTV) organopolysiloxane compositions are known. In particular, dealcohol-curing types, which cure by releasing alcohol through a hydrolysis and condensation reaction during crosslinking, are preferred for use in sealing, bonding, and coating electrical and electronic devices, etc., due to their lack of unpleasant odor and non-corrosive properties against metals (Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2003-147203 [Patent Document 2] Patent No. 5997778 Summary of the Invention [Problem to be solved by the invention]

[0006] However, compared to other conventionally known curing types such as the acetone-free, oxime-free, and aminoxy-free types, the alcohol-free type has a lower reactivity with water (moisture) in the atmosphere and a slower curing rate. Therefore, until now, there have been no hydrolyzable organosilane compounds that can serve as chain extenders for silicone polymers (main components) in industrially practical alcohol-free room-temperature vulcanizable (RTV) compositions, and no compositions containing such compounds have been available.

[0007] Therefore, an object of the present invention is to provide a room-temperature-curable resin composition containing, as a chain extender, a hydrolyzable organosilane compound that quickly becomes rubber and exhibits appropriate elongation due to its chain-extending effect; a coating agent, adhesive, and sealant made from the room-temperature-curable resin composition; and an article that is coated, adhered, or sealed with a cured product of the room-temperature-curable resin composition. [Means for solving the problem]

[0008] As a result of intensive research conducted by the present inventors to achieve the above-mentioned object, they discovered that a room-temperature-curable resin composition containing a specific organoxymethylene group-containing organosilane compound represented by the following formula (1) is useful for solving the above-mentioned problems, and thus completed the present invention.

[0009] That is, the present invention provides the following room-temperature-curable resin compositions (specifically, coating agents, adhesives, and sealants), as well as articles having a cured product of the composition.

[0010] [1] (A) a silicone polymer having both molecular chain terminals blocked with silanol groups or hydrolyzable silyl groups: 100 parts by mass, (B) an organoxymethylene group-containing organosilane compound represented by the following formula (1): 0.001 to 30 parts by mass, [ka] (In the formula, R 1 , R 2 and R 3 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms. (C) a crosslinking agent other than component (B): 0.001 to 30 parts by mass, and (D) Curing catalyst: 0.001~20 parts by mass A room-temperature curable resin composition comprising: [2] Furthermore, for 100 parts by mass of component (A), (E) Filler: 1 to 1,000 parts by mass The room-temperature-curable resin composition according to [1], which contains [3] A coating agent comprising the room-temperature-curable resin composition according to [1] or [2]. [4] An adhesive comprising the room-temperature-curable resin composition according to [1] or [2]. [5] A sealant comprising the room-temperature-curable resin composition according to [1] or [2]. [6] An article having a coating layer made of a cured product of the room-temperature-curable resin composition according to [1] or [2]. [7] An article bonded and / or sealed with a cured product of the room-temperature-curable resin composition according to [1] or [2]. [Effects of the Invention]

[0011] The room-temperature-curable resin composition of the present invention contains a specific organoxymethylene group-containing organosilane compound, which allows it to cure extremely quickly and, due to the chain extension effect, provides the cured rubber with an appropriate elongation. DETAILED DESCRIPTION OF THE INVENTION

[0012] The present invention will be described in more detail below.

[0013] Component (A) The component (A) used in the present invention is a silicone polymer (main component) whose molecular chain is terminated at both ends with silanol groups (hydroxyl groups bonded to silicon atoms) or hydrolyzable silyl groups such as alkoxysilyl groups, e.g., trialkoxysilyl groups and dialkoxyorganosilyl groups. Such silicone polymers are preferably silicone polymers (organopolysiloxanes).

[0014] Specifically, the silicone polymer used is a linear diorganopolysiloxane represented by the following formula (2) or (3), in which both molecular chain terminals are blocked with silanol groups or hydrolyzable silyl groups. [ka] (R in the formula 4is an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, X is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, Y is a hydrolyzable group, and b is 0 or 1. m is a number that gives the diorganopolysiloxane a viscosity of 100 to 1,000,000 mPa s at 23°C, and is an average number of 30 to 2,000, preferably 50 to 1,200, and more preferably about 100 to 800. The viscosity is a value measured using a rotational viscometer (e.g., BL type, BH type, BS type, cone-plate type, etc.) (the same applies hereinafter.) The number of repeating diorganosiloxane units (m) or degree of polymerization in the diorganopolysiloxane represented by formula (2) or (3) above is 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.

[0015] In the above formulas (2) and (3), R 4 Examples of the unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or the unsubstituted or substituted aryl group having 6 to 10 carbon atoms include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; aryl groups such as phenyl, tolyl, xylyl, and α- and β-naphthyl; 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, alkyl groups such as methyl and ethyl are preferred, with methyl being particularly preferred.

[0016] In the above formulas (2) and (3), X is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, and is represented by -(CH2CH2) q - or -(CH=CH) qPreferably, it is - (q represents 1 to 4). Among these, an oxygen atom, -CH2CH2-, or -CH=CH- is particularly preferred.

[0017] In the above formula (3), Y is a hydrolyzable group, for example, 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, allyloxy, propenyloxy, isopropenyloxy, 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 preferred, and methoxy, ethoxy, and propoxy groups are particularly preferred.

[0018] Examples of the structure of the linear diorganopolysiloxane represented by formula (2) or (3) above include diorganopolysiloxanes capped at both molecular chain terminals with silanol groups, diorganopolysiloxanes capped at both molecular chain terminals with diorganohydroxysilylethyl groups, diorganopolysiloxanes capped at both molecular chain terminals with diorganohydroxysilylpropyl groups, diorganopolysiloxanes capped at both molecular chain terminals with trialkoxysiloxy groups, diorganopolysiloxanes capped at both molecular chain terminals with dialkoxyorganosiloxy groups, diorganopolysiloxanes capped at both molecular chain terminals with trialkoxysilylethyl groups, diorganopolysiloxanes capped at both molecular chain terminals with trialkoxysilylpropyl groups, diorganopolysiloxanes capped at both molecular chain terminals with dialkoxyorganosilylethyl groups, and diorganopolysiloxanes capped at both molecular chain terminals with dialkoxyorganosilylpropyl groups.

[0019] The silicone polymer of component (A) in which both molecular chain terminals are blocked with silanol groups or hydrolyzable silyl groups may be used either alone or in combination of two or more types with different structures or degrees of polymerization.

[0020] (B) Component The composition of the present invention comprises a bifunctional hydrolyzable organosilane compound represented by the following formula (1), which contains an organoxymethylene group such as a methoxymethyl group or an ethoxymethyl group (i.e., an organoxy-substituted methyl group or an α-organoxy group) on a silicon atom, and which also has two organoxy groups (e.g., a methoxy group, an ethoxy group, etc.) directly bonded to the same silicon atom. The organoxymethylene group-containing organosilane compound of component (B) acts as a chain extender in the composition of the present invention, by forming Si-O-Si bonds (siloxane bonds) through a condensation reaction between the two organoxy groups directly bonded to silicon atoms in component (B) and the silanol groups or hydrolyzable silyl groups present at both ends of the silicone polymer of component (A). [ka] (In the formula, R 1 , R 2 and R 3 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms.

[0021] In the formula, R 1 , R 2 and R 3 each independently represents an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms. 1 , R 2 and R 3In the formula, the alkyl group having 1 to 10 carbon atoms may be linear, cyclic, or branched. Specific examples thereof include linear or branched alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl; and cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and isobornyl. Specific examples of aryl groups having 6 to 10 carbon atoms include phenyl, tolyl, xylyl, α-naphthyl, and β-naphthyl. Some or all of the hydrogen atoms in these groups may be substituted with alkyl groups, aryl groups, halogen atoms such as F, Cl, and Br, or cyano groups. Among these, R 1 , R 2 and R 3 As the alkyl group, alkyl groups such as methyl and ethyl groups, and phenyl groups are preferred, with methyl groups being more preferred in terms of reactivity, availability, productivity, and cost.

[0022] Specific examples of component (B) include dialkoxy(alkyl)(alkoxymethyl)silanes such as dimethoxy(methyl)(methoxymethyl)silane, diethoxy(methyl)(methoxymethyl)silane, dimethoxy(methyl)(ethoxymethyl)silane, diethoxy(methyl)(ethoxymethyl)silane, dimethoxy(ethyl)(methoxymethyl)silane, diethoxy(ethyl)(methoxymethyl)silane, dimethoxy(ethyl)(ethoxymethyl)silane, and diethoxy(ethyl)(ethoxymethyl)silane. The organoxymethylene group-containing organosilane compound of component (B) may be used alone or in combination of two or more different compounds. The amount of component (B) added is 0.001 to 30 parts by mass, and preferably 0.01 to 20 parts by mass, per 100 parts by mass of component (A).

[0023] (C) Component Component (C) used in the composition of the present invention is a crosslinking agent other than the organoxymethylene group-containing organosilane compound of component (B), and can be a hydrolyzable (organo)silane compound and / or its partial hydrolysis condensate. Component (C) acts as a curing agent (crosslinking agent) that crosslinks and cures the composition of the present invention.

[0024] Specific examples of component (C) include trialkoxysilanes such as methyltrimethoxysilane, ethyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, vinyltriethoxysilane, and phenyltriethoxysilane; trialkenyloxysilanes such as triisopropenoxysilanes such as methyltriisopropenoxysilane, ethyltriisopropenoxysilane, vinyltriisopropenoxysilane, and phenyltriisopropenoxysilane; methyltriacetoxysilanes; Examples of suitable hydrolyzable (organo)silanes include triacyloxysilanes such as triacetoxysilanes (e.g., ethyltriacetoxysilane, vinyltriacetoxysilane), tetraethoxysilane, tetramethoxysilane, ethyl silicate, and methyl silicate, which have three or four, and preferably three, hydrolyzable groups per molecule, and partial hydrolysis condensates of these silanes (organosiloxane oligomers obtained by partial hydrolysis and condensation of the silane compounds and having at least two, and preferably three or more, residual hydrolyzable groups per molecule). These may be used singly or in combination of two or more. Component (C) does not contain a monovalent hydrocarbon group containing a functional group with a heteroatom in the molecule, and in this respect is clearly distinguished from carbon functional silane (silane coupling agent), which is the adhesion promoter for component (F) described below.

[0025] The amount of component (C) blended is 0.001 to 30 parts by mass, and preferably 0.01 to 10 parts by mass, per 100 parts by mass of component (A). If the amount of component (C) blended is too small, sufficient curing properties will not be obtained, while if the amount is too large, the curing will be too rapid, resulting in insufficient working time and possibly being economically disadvantageous.

[0026] (D) Component The component (D) used in the composition of the present invention is a curing catalyst (a non-metallic organic catalyst and / or a metallic catalyst) that acts to accelerate the curing of the room-temperature-curable resin composition of the present invention.

[0027] The non-metallic organic catalyst used as the curing catalyst may be any known curing accelerator for condensation-curable organopolysiloxane compositions, and is not particularly limited. Examples of the non-metallic organic catalyst include phosphazene-containing compounds such as N,N,N',N',N'',N''-hexamethyl-N'''-(trimethylsilylmethyl)phosphorimidic triamide; amine compounds or salts thereof such as n-octylamine, hexylamine, dodecylamine phosphate, and tetramethylguanidine; quaternary ammonium salts such as benzyltriethylammonium acetate; dialkylhydroxylamines such as dimethylhydroxylamine and diethylhydroxylamine; and hydrolyzable silanes and siloxanes containing a guanidyl group such as tetramethylguanidylpropyltrimethoxysilane, tetramethylguanidylpropylmethyldimethoxysilane, and tetramethylguanidylpropyltris(trimethylsiloxy)silane. Furthermore, the non-metallic organic catalyst may be used alone or in combination of two or more.

[0028] The metal catalyst of the curing catalyst may be any known curing accelerator for condensation curing organopolysiloxanes, and is not particularly limited. For example, alkyl tin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctoate, dioctyltin dineodecanoate, and di-n-butyl-dimethoxytin, titanate esters or titanium chelate compounds such as tetraisopropoxytitanium, tetra-n-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, dipropoxybis(acetylacetonato)titanium, and titanium isopropoxyoctylene glycol, zinc naphthenate, zinc stearate, zinc-2-ethyloctoate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2 Examples of metal catalysts include, but are not limited to, aluminum alcoholate compounds such as aluminum ethyl hexanoate, cobalt naphthenate, aluminum isopropylate, and aluminum secondary butylate; aluminum chelate compounds such as aluminum alkyl acetate diisopropylate and aluminum bisethylacetoacetate monoacetylacetonate; organometallic compounds such as bismuth(III) neodecanoate, bismuth(III) 2-ethylhexanoate, bismuth(III) citrate, and bismuth octoate; and alkali metal salts of lower fatty acids such as potassium acetate, sodium acetate, and lithium oxalate. Metal catalysts may be used singly or in combination.

[0029] The amount of the curing catalyst for component (D) is 0.001 to 20 parts by mass, and preferably 0.01 to 10 parts by mass, per 100 parts by mass of component (A). If the amount of component (D) is too small, the composition will not cure sufficiently, while if the amount is too large, the composition will cure too quickly, resulting in insufficient working time and possibly being economically disadvantageous.

[0030] (E) Component Component (E) is a filler (inorganic filler and / or organic resin filler) that can be optionally incorporated into the composition of the present invention to impart sufficient mechanical strength to the cured product formed from this composition. Known fillers can be used, including, for example, finely divided silica, fumed silica, precipitated silica, silica whose surface has been hydrophobized with an organosilicon compound, glass beads, glass balloons, transparent resin beads, silica aerogel, diatomaceous earth, metal oxides such as iron oxide, zinc oxide, titanium oxide, and fumed metal oxides, wet silica or silica whose surface has been silane-treated, quartz powder, reinforcing agents such as carbon black, talc, zeolite, and bentonite, asbestos, glass fiber, carbon fiber, metal carbonates such as calcium carbonate, heavy calcium carbonate, magnesium carbonate, and zinc carbonate, glass wool, finely divided mica, fused silica powder, and synthetic resin powders such as polystyrene, polyvinyl chloride, and polypropylene. Of these fillers, inorganic fillers such as silica, calcium carbonate, and zeolite are preferred, and fumed silica and calcium carbonate whose surfaces have been treated to be hydrophobic are particularly preferred.

[0031] The amount of filler (E) blended is preferably 0 to 1,000 parts by mass, particularly 1 to 1,000 parts by mass, and especially 1 to 400 parts by mass per 100 parts by mass of component (A). The cured product obtained from this composition tends to exhibit sufficient mechanical strength when blended rather than when not blended, but 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 tends to decrease, making it difficult to obtain rubber elasticity.

[0032] (F) Component Component (F) is an adhesion promoter (carbon functional silane (silane coupling agent)), which is an optional component that can be incorporated into the composition of the present invention as needed, and is used to impart sufficient adhesion to a cured product formed from this composition. Specifically, it is preferable to blend hydrolyzable organosilane compounds (so-called carbon functional silanes, or silane coupling agents) having in the molecule a monovalent hydrocarbon group containing a functional group (excluding guanidyl groups) having a heteroatom such as a nitrogen atom, oxygen atom, or sulfur atom, such as aminosilanes such as γ-aminopropyltriethoxysilane and 3-2-(aminoethylamino)propyltrimethoxysilane; epoxysilanes such as γ-glycidoxypropyltrimethoxysilane and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane; (meth)acrylic silanes such as γ-(meth)acryloxypropyltrimethoxysilane and γ-(meth)acryloxypropyltriethoxysilane; mercaptosilanes such as γ-mercaptopropyltrimethoxysilane; and isocyanate silanes such as γ-isocyanatopropyltrimethoxysilane. Component (F) contains a monovalent hydrocarbon group containing a functional group having a heteroatom in the molecule, and in this respect is clearly distinguishable from the hydrolyzable (organo)silane compound and / or its partial hydrolysis condensate, which are the aforementioned component (C).

[0033] The amount of the adhesion promoter (F) to be blended is preferably 0 to 30 parts by mass, particularly 0.1 to 30 parts by mass, and especially 0.1 to 20 parts by mass, per 100 parts by mass of the component (A). If the amount exceeds 30 parts by mass, the curability may be insufficient, or this may be economically disadvantageous.

[0034] (G) Component Component (G) is a plasticizer, an optional component that can be blended into the composition of the present invention as needed, and can adjust the viscosity to be easy to handle in application without impairing the mechanical properties or flame retardancy of the cured product formed from this composition.

[0035] Examples of the plasticizer that can be used in the 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), and ethylene tetrahydrophthalate. esters, dioctyl adipate (DOA), diisononyl adipate (DINA), diisodecyl adipate (DIDA), di-n-alkyl adipates, dibutyl diglycol adipate (BXA), bis(2-ethylhexyl) azelaate (DOZ), dibutyl sebacate (DBS), dioctyl sebacate (DOS), dibutyl maleate (DBM), di-2-ethylhexyl maleate (DOM), dibutyl fumarate (DBF), Examples of suitable plasticizers include tricresyl phosphate (TCP), triethyl phosphate (TEP), tributyl phosphate (TB20P), 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. Other suitable plasticizers include trimellitic acid-based plasticizers, polyester-based plasticizers, chlorinated paraffin, and stearic acid-based plasticizers. Other suitable plasticizers include silicone oils (non-functional organopolysiloxanes) such as dimethylpolysiloxane, and petroleum-based high-boiling solvents such as polyoxypropylene glycols, paraffins, naphthenes, and isoparaffins. These may be used alone or in combination of two or more. Among these, silicone oil is particularly preferred.

[0036] It is preferable to use an organopolysiloxane represented by the following formula (4) (diorganopolysiloxane blocked at both molecular chain terminals with triorganosiloxy groups) as the above silicone oil (non-functional organopolysiloxane). [ka] (In the formula, R 5 are each independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms and containing no aliphatic unsaturated bonds, and n is a number that gives the organopolysiloxane a viscosity of 1.5 to 1,000,000 mPa s at 23°C.

[0037] In the above formula (4), R 5 are each independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms and containing no aliphatic unsaturated bonds. Specific examples include alkyl groups such as methyl, ethyl, n-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 a chloromethyl, chloropropyl, bromoethyl, or trifluoropropyl group.

[0038] In the organopolysiloxane represented by the above formula (4), the value of n, which indicates the number of repetitions of the diorganosiloxane unit (degree of polymerization), may be an integer of about 3 to 3,000, preferably 5 to 2,000, and more preferably 10 to 1,000.

[0039] The blend amount of component (G) is preferably 0 to 1,000 parts by mass, more preferably 1 to 1,000 parts by mass, and even more preferably 1 to 200 parts by mass, per 100 parts by mass of component (A). When the amount of component (G) is within the above range, the viscosity of the composition of the present invention can be adjusted to a level that is easy to handle during application, without impairing the mechanical properties or flame retardancy of the composition, which is preferred.

[0040] [Other ingredients] The composition of the present invention may further contain known additives, such as pigments, dyes, antioxidants, antioxidants, antistatic agents, flame retardants such as antimony oxide and chlorinated paraffin, as well as polyethers as thixotropy improvers, mildew inhibitors, and antibacterial agents, if necessary.

[0041] Furthermore, the composition of the present invention may contain an organic solvent as needed. Examples of organic solvents 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 organic solvent may be adjusted as needed within a range that does not impair the effects of the present invention.

[0042] The composition of the present invention can be used as a one-component composition, or a multi-component composition of two or more components.

[0043] The composition of the present invention can be obtained by uniformly mixing the above-mentioned components and the above-mentioned various additives in predetermined amounts in a dry atmosphere. The composition of the present invention cures by leaving it at room temperature, and the molding method, curing conditions, etc. can be known methods and conditions depending on the type of composition.

[0044] The compositions of the present invention, particularly one-component compositions, are readily cured at room temperature (23°C ± 15°C) in the absence of water (moisture), i.e., by storing them in a sealed container that is protected from moisture, and by exposing them to water in the air when used. Two-component or higher multi-component compositions are readily cured at room temperature (23°C ± 15°C) in the absence of water, i.e., by storing them in a sealed container that is protected from moisture, and by mixing the individually stored compositions together in the presence of water in the air when used.

[0045] Furthermore, the cured product of the composition of the present invention (cured silicone rubber product) exhibits good flexibility and has rubber elasticity, and is therefore useful as a coating agent, adhesive, or sealant (for example, a construction sealant, etc.) The method of using the composition of the present invention as a coating agent, adhesive, or sealant may be any conventionally known method, and is not particularly limited.

[0046] Examples of articles having a coating layer made of a cured product of the 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.

[0047] Examples of articles that can be bonded and / or sealed with a cured product of the composition of the present invention include articles made of glass, various metals, etc., but the material and shape of the substrate are not particularly limited. [Example]

[0048] 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 using a rotational viscometer at 23°C.

[0049] [Example 1-1] Composition 1 was obtained by adding 1.0 part by mass of n-octylamine, 0.6 part by mass of dioctyltin dineodecanoate, 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane, and 0.3 parts by mass of vinyltrimethoxysilane to 100 parts by mass of dimethylpolysiloxane having a viscosity of 5,000 mPa·s and having both molecular chain terminals blocked with hydroxyl groups (silanol groups). The mixture was then mixed uniformly while protected from moisture.

[0050] [Example 1-2] Composition 2 was obtained in the same manner as in Example 1-1, except that 1.0 part by mass of tetramethylguanidine was used instead of 1.0 part by mass of n-octylamine.

[0051] [Comparative Example 1-1] Composition 3 was obtained in the same manner as in Example 1-1, except that 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane was not added.

[0052] [Comparative Example 1-2] Composition 4 was obtained in the same manner as in Example 1-2, except that 1.2 parts by mass of dimethyldimethoxysilane was blended in place of 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane.

[0053] [Example 2-1] 100 parts by mass of dimethylpolysiloxane with a viscosity of 5,000 mPa s and both molecular chain terminals blocked with hydroxyl groups (silanol groups) was dispersed and mixed with 80 parts by mass of surface-treated calcium carbonate (trade name: Viscoexcel 30K, manufactured by Shiraishi Kogyo Co., Ltd.) and 60 parts by mass of heavy calcium carbonate (trade name: Super S, manufactured by Maruo Calcium Co., Ltd.) until the mixture was uniform. Then, 5.0 parts by mass of tetramethylguanidylpropyltrimethoxysilane, 3.0 parts by mass of dioctyltin dineodecanoate, 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane, and 0.3 parts by mass of vinyltrimethoxysilane were added and thoroughly mixed under reduced pressure to obtain Composition 5.

[0054] [Example 3-1] Composition 6 was obtained in the same manner as in Example 1-1, except that 1.0 part by mass of 3-(2-aminoethylamino)propyltrimethoxysilane was further added as an adhesion promoter.

[0055] [Example 3-2] Composition 7 was obtained in the same manner as in Example 3-1, except that 1.0 part by mass of 3-aminopropyltrimethoxysilane was used instead of 1.0 part by mass of 3-(2-aminoethylamino)propyltrimethoxysilane.

[0056] [Example 4-1] Composition 8 was obtained in the same manner as in Example 1-1, except that 10 parts by mass of a dimethylpolysiloxane capped at both molecular chain terminals with trimethylsiloxy groups and having a viscosity of 100 mPa·s was further blended as a plasticizer.

[0057] [Example 4-2] Composition 9 was obtained in the same manner as in Example 1-1, except that 20 parts by mass of a dimethylpolysiloxane capped at both molecular chain terminals with trimethylsiloxy groups and having a viscosity of 100 mPa·s was further blended as a plasticizer.

[0058] [Comparative Example 2-1] Composition 10 was obtained in the same manner as in Example 2-1, except that 2.2 parts by mass of 1,3-dimethyl-1,3-di(methoxymethyl)-1,3-divinyl-disiloxane was used instead of 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane.

[0059] [Comparative Example 2-2] Composition 11 was obtained in the same manner as in Example 2-1, except that 1.2 parts by mass of dimethyldimethoxysilane was used instead of 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane.

[0060] [Comparative Example 3-1] Composition 12 was obtained in the same manner as in Example 3-1, except that 1.2 parts by mass of dimethyldimethoxysilane was blended in place of 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane.

[0061] [Comparative Example 3-2] Composition 13 was obtained in the same manner as in Example 3-2, except that 1.2 parts by mass of dimethyldimethoxysilane was blended in place of 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane.

[0062] [Comparative Example 4-1] Composition 14 was obtained in the same manner as in Example 4-1, except that 1.2 parts by mass of dimethyldimethoxysilane was blended in place of 1.5 parts by mass of dimethoxy(methyl)(methoxymethyl)silane.

[0063] 〔test〕 Immediately after preparation, each composition prepared in Examples 1-1 to 4-2 and Comparative Examples 1-1 to 4-1 was extruded into a 2 mm thick sheet and exposed to air at 23°C and 50% RH. The sheet was then left to stand in the same atmosphere for 7 days, and the physical properties (initial physical properties) of the resulting cured product were measured in accordance with JIS K-6249. Hardness was measured using a JIS K-6249 Durometer A hardness tester or an Asker C hardness tester.

[0064] [Table 1]

[0065] [Table 2]

[0066] The results in Table 1 reveal that Examples 1-1 and 1-2 have better reactivity and exhibit higher curability than the corresponding Comparative Examples 1-1 and 1-2.

[0067] The results in Table 2 reveal that Examples 2-1 to 4-2 exhibit higher curability and higher elongation due to the chain extension effect, compared to the corresponding Comparative Examples 2-1 to 4-1.

Claims

1. (B) The following formula (1): 【Chemistry 1】 (In the formula, R 1 , R 2 and R 3 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms. A chain extender comprising an organoxymethylene group-containing organosilane compound represented by the formula: (A) 100 parts by mass of a silicone polymer composed of a linear diorganopolysiloxane whose molecular chain ends are capped with silanol groups or hydrolyzable silyl groups, represented by the following formula (2) or (3): 【Chemistry 2】 (Wherein, R in formulas (2) and (3) 4 is an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, X in formula (2) is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, X in formula (3) is an oxygen atom, Y in formula (3) is a hydrolyzable group, and b in formula (3) is 0 or 1. m in formulas (2) and (3) is a number that gives the diorganopolysiloxane a viscosity at 23°C of 100 to 1,000,000 mPa·s, and is a number that averages 30 to 2,000. (B) the chain extender, which is an organoxymethylene group-containing organosilane compound represented by formula (1): 0.001 to 30 parts by mass, (C) a crosslinking agent other than component (B): 0.001 to 30 parts by mass, and (D) Curing catalyst: 0.001 to 20 parts by mass (However, this does not include the case where the curing catalyst (D) contains one or more compounds selected from the group consisting of non-silicon organic compounds, hydrolyzable organosilane compounds, and partial hydrolysis condensates thereof, each having at least one guanidine skeleton per molecule.)

2. The room-temperature-curable resin composition further contains, per 100 parts by mass of the component (A), (E) Filler: 1 to 1,000 parts by mass The chain extender according to claim 1, which comprises:

3. A room-temperature-curable resin composition using the chain extender according to claim 1, (A) 100 parts by mass of a silicone polymer composed of a linear diorganopolysiloxane whose molecular chain ends are capped with silanol groups or hydrolyzable silyl groups, represented by the following formula (2) or (3): 【Transformation 3】 (Wherein, R in formulas (2) and (3) 4 is an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms, X in formula (2) is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, X in formula (3) is an oxygen atom, Y in formula (3) is a hydrolyzable group, and b in formula (3) is 0 or 1. m in formulas (2) and (3) is a number that gives the diorganopolysiloxane a viscosity at 23°C of 100 to 1,000,000 mPa·s, and is a number that averages 30 to 2,000. (B) the organoxymethylene group-containing organosilane compound represented by formula (1), which is the chain extender according to claim 1: 0.001 to 30 parts by mass, (C) a crosslinking agent other than component (B): 0.001 to 30 parts by mass, and (D) Curing catalyst: 0.001 to 20 parts by mass (However, this does not include the case where the curing catalyst (D) contains one or more compounds selected from the group consisting of non-silicon organic compounds having at least one guanidine skeleton in one molecule, hydrolyzable organosilane compounds, and partial hydrolysis condensates thereof.)

4. A coating agent comprising the room temperature curable resin composition according to claim 3.

5. An adhesive comprising the room temperature curable resin composition according to claim 3.

6. A sealant comprising the room temperature curable resin composition according to claim 3.

7. An article having a coating layer made of a cured product of the room-temperature-curable resin composition according to claim 3.

8. An article bonded and / or sealed with a cured product of the room-temperature-curable resin composition according to claim 3.

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