Organopolysiloxane having reactive silicon-containing group, production method therefor, curable composition, and cured product

Abstract

This reactive silicon group-containing organopolysiloxane has, in each molecule, at least one group represented by structural formula (1) bonded to a silicon atom. The reactive silicon group-containing organopolysiloxane has good curability even if an amine-based compound is used as a curing catalyst, and gives a cured product having excellent yellowing resistance and heat resistance. (In the formula, R1 and R2 each independently represent a hydrogen atom, a C1-10 aliphatic saturated hydrocarbon group or a C6-10 aryl group, each R3 independently represents a C1-10 aliphatic saturated hydrocarbon group or a C6-10 aryl group, and n is an integer of 2-12. The wavy line represents a bond.)

Description

Organopolysiloxane having reactive silicon-containing groups, its production method, curable composition, and cured product

[0001] The present invention relates to an organopolysiloxane having a reactive silicon-containing group, a method for producing the same, a curable composition, and a cured product thereof. More specifically, the present invention relates to an organopolysiloxane having, as the reactive silicon-containing group, an organosilicon group that can react to form a siloxane bond, a method for producing the same, a curable composition, and a cured product thereof.

[0002] Reactive silicon groups, especially alkoxysilyl groups, have the property of hydrolysis and condensation in the presence of water, so compounds having this reactive silicon group can be used as curable compositions that crosslink and cure in the presence of water or humidity.Among these compounds, those whose main chain is a silicon-containing organic group such as silicone are generally known as terminally reactive silicones, etc.In addition, the curable compositions using these have the characteristic of being liquid at room temperature and becoming rubber elastic bodies when cured, and are widely used in coating agents, adhesives, construction sealants, etc. by utilizing this characteristic.

[0003] Various types of room temperature curable compositions containing reactive silicone terminals are known depending on the type of reactive silicon group, but conventionally, those in which the reactive silicon group is an alkoxysilyl group, i.e., dealcoholization types that cure by releasing alcohol, have been preferred for the above-mentioned applications because they do not emit unpleasant odors and do not corrode metals. A typical example of this dealcoholization type is a room temperature curable composition that uses an alkoxysilyl-terminated silicone oil as the main component (base polymer), as disclosed in Patent Document 1.

[0004] However, the dealcohol-type room-temperature curable composition of Patent Document 1 has lower reactivity with moisture in the air and insufficient curing ability compared to other conventionally known curing types such as oxime-depleted, acetic acid-depleted, and acetone-depleted types, and therefore generally requires the addition of a catalyst such as an organotin compound to ensure sufficient curing ability at room temperature, but the organotin compounds typically used as catalysts are toxic to humans and the environment. Furthermore, when an organometallic catalyst such as an organotin compound is used in a dealcohol-type room-temperature curable composition, the main chain of the silicone oil is cleaved (cracked) by the generated alcohol, resulting in poor storage stability such as a decrease in curing ability and thickening over time.

[0005] Therefore, Patent Document 2 discloses a room-temperature curable composition comprising an alkoxysilyl-terminated silicone oil containing a silethylene group as a linking group between the alkoxysilyl group and the silicone oil main chain in order to improve storage stability. However, although the compound of Patent Document 2 has good storage stability, it still has insufficient curability. Furthermore, when an amine-based compound is used as a curing catalyst for this compound to eliminate the use of organotin-based compounds, which are toxic, there is also the problem of low reactivity and long curing times.

[0006] Furthermore, Patent Document 3 discloses an alkoxysilyl end-blocked polymer obtained by reacting a polymer having a hydroxyl group at the end with an isocyanate silane or the like to improve reactivity. However, although the compound of Patent Document 3 has excellent reactivity, it contains a urethane or urea bond in the molecule, which causes significant discoloration over time and insufficient yellowing resistance and heat resistance. Furthermore, the use of a highly toxic low-boiling point isocyanate silane in the production of the end-blocked polymer, and the possibility of similar low-boiling point isocyanate silane being generated by thermal decomposition of the urethane or urea bond at high temperatures, are considered problematic.

[0007] Furthermore, Patent Document 4 discloses that by using a specific organopolysiloxane group-containing organosilicon compound having a sulfide-methylene bond as the linking group between the alkoxysilyl group and the organopolysiloxane main chain, a cured product can be obtained that exhibits excellent rapid curing properties and excellent yellowing resistance even when an amine compound is used as the curing catalyst instead of an organotin compound, and that does not use isocyanate silane, which can result in low toxicity. However, although the compound in Patent Document 4 exhibits excellent reactivity when an amine catalyst is used, there is a problem in that the cured product softens due to cleavage of the sulfide-methylene-silicon bond at high temperatures.

[0008] Japanese Patent Laid-Open No. 55-43119 Japanese Patent Publication No. 7-39547 Special Publication No. 2004-518801 Japanese Patent Laid-Open No. 2017-203025

[0009] The present invention has been made in view of the above circumstances, and has as its object to provide a reactive silicon group-containing organopolysiloxane that exhibits good curability even when an amine compound is used as a curing catalyst, and that gives a cured product that is excellent in yellowing resistance and heat resistance, as well as a method for producing the same.

[0010] As a result of extensive research aimed at solving the above problems, the present inventors have discovered that organopolysiloxanes having, as reactive silicon groups, an organoxymethyl group and a silyl group to which two organoxy groups are bonded exhibit good curability even when an amine compound is used as a curing catalyst, and give cured products that are excellent in yellowing resistance and heat resistance, thereby completing the present invention.

[0011] That is, the present invention provides: 1. A reactive silicon group-containing organopolysiloxane having one or more groups bonded to silicon atoms and represented by the following structural formula (1) in each molecule; (In the formula, R 1 and R 2 each independently represents a hydrogen atom, an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms; R 3each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and n is an integer from 2 to 12. A wavy line represents a bond. 2. A reactive silicon group-containing organopolysiloxane of formula 1 represented by the following formula (2): (In the formula, R 1 , R 2 , R 3 and n have the same meaning as above, R 4 each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and p is an integer of 1 to 2,000. 3. A disiloxane compound represented by the following formula (3): (In the formula, R 1 and R 2 are each independently a hydrogen atom, an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and R 3 are each independently an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.) 4. A method for producing a reactive silicon group-containing organopolysiloxane according to 1, which comprises subjecting an organopolysiloxane containing an alkenyl group bonded to a silicon atom to a hydrosilylation reaction with a disiloxane compound represented by the following formula (3): (In the formula, R 1 , R 2 and R 3 has the same meaning as above.) 5. A method for producing a reactive silicon group-containing organopolysiloxane according to 4, wherein the organopolysiloxane containing alkenyl groups bonded to silicon atoms is represented by the following formula (4): (In the formula, R 4 each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms; R 5represents an alkenyl group having 2 to 12 carbon atoms, and p is an integer from 1 to 2000.) 6. A curable composition containing (A) the reactive silicon group-containing organopolysiloxane of 1 and (B) a curing catalyst, 7. The curable composition of 6 in which the (B) curing catalyst is an amine-based compound, 8. A cured product obtained by curing the curable composition of 6 or 7, 9. A coating composition containing (A) the reactive silicon group-containing organopolysiloxane of 1 and (B) a curing catalyst, 10. The coating composition of 9 in which the (B) curing catalyst is an amine-based compound, 11. An article having a coating layer obtained by curing the coating composition of 9 or 10, 12. An adhesive composition containing (A) the reactive silicon group-containing organopolysiloxane of 1 and (B) a curing catalyst, 13. The adhesive composition of 12 in which the (B) curing catalyst is an amine-based compound, 14. 14. An article having an adhesive layer formed by curing the adhesive composition of 12 or 13.

[0012] The reactive silicon group-containing organopolysiloxane of the present invention has an organoxymethyl group and a silyl group to which two organoxy groups are bonded as specific reactive silicon groups at the molecular terminal, and therefore exhibits good curability even when an amine compound is used as a curing catalyst instead of an organotin compound, and gives a cured product with excellent yellowing resistance and heat resistance. The reactive silicon group-containing organopolysiloxane of the present invention, which has such properties, can be suitably used as a main component (base polymer) in coating agents, adhesives, sealants, etc.

[0013] The present invention will now be described in detail. The reactive silicon group-containing organopolysiloxane of the present invention is an organopolysiloxane containing, per molecule, at least one group bonded to a silicon atom and represented by the following structural formula (1):

[0014]

[0015] In formula (1), R 1 and R 2 each independently represents a hydrogen atom, an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms; R 3R each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms. 1 , R 2 and R 3 The aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms may be linear, cyclic, or branched, and 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 groups; and cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. 1 , R 2 and R 3 Specific examples of the aryl group having 6 to 10 carbon atoms include phenyl, tolyl, xylyl, α-naphthyl, β-naphthyl, etc. Some or all of the hydrogen atoms in these groups may be substituted with halogen atoms such as F, Cl, Br, etc., or cyano groups, etc. Specific examples thereof include 3-chloropropyl, 3,3,3-trifluoropropyl, 2-cyanoethyl, etc.

[0016] Among these, R 1 , R 2 and R 3 As the alkyl group, a methyl group, an ethyl group, or a phenyl group is preferred, and from the viewpoints of curability, productivity, and cost, a methyl group is more preferred.

[0017] In formula (1), n ​​is an integer of 2 to 12, preferably 2 to 8, more preferably 2 or 3, and even more preferably 2, from the viewpoint of reactivity.

[0018] The siloxane structural units (M units, D units, T units, and Q units) of the reactive silicon group-containing organopolysiloxane of the present invention are not particularly limited, and may have a linear, branched, cyclic, or crosslinked structure in the siloxane skeleton, but a linear structure is preferred from the viewpoint of the mechanical properties of the resulting cured product and the storage stability of the composition.

[0019] In the reactive silicon group-containing organopolysiloxane of the present invention, the number of reactive silicon-containing groups represented by the above structural formula (1) contained in one molecule is one or more, but from the viewpoints of the curability and storage stability of the composition and the mechanical properties of the cured product, the number is preferably two to four, and more preferably two (for example, one at each end of the molecular chain of a linear organopolysiloxane).

[0020] Therefore, the reactive silicon group-containing organopolysiloxane of the present invention is preferably one represented by the following formula (2), and the use of such a compound further improves the mechanical properties of the resulting cured product and the storage stability of the composition.

[0021] (In the formula, R 1 , R 2 , R 3 and n have the same meaning as above.)

[0022] In formula (2), R 4 R each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms. 4 The aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms and the aryl group having 6 to 10 carbon atoms are the same as those of the above R 1 , R 2 and R 3 Among these, a methyl group, an ethyl group, and a phenyl group are preferred, and from the viewpoint of yellowing resistance of the cured product, a methyl group is more preferred.

[0023] In formula (2), p is a number from 1 to 2,000, but from the viewpoint of the mechanical properties of the resulting cured product and the workability of the composition, it is preferably 10 to 1,500, and more preferably 100 to 1,000.

[0024] The number average molecular weight of the reactive silicon group-containing organopolysiloxane of the present invention is not particularly limited, but in consideration of improving workability and imparting sufficient curability while maintaining the viscosity and other properties of the curable composition containing the compound within an appropriate range, the number average molecular weight is preferably 200 to 100,000, more preferably 500 to 50,000, and even more preferably 1,000 to 20,000. Note that the number average molecular weight in the present invention is a polystyrene-equivalent value determined by gel permeation chromatography (GPC) analysis (the same applies hereinafter).

[0025] Furthermore, the viscosity of the reactive silicon group-containing organopolysiloxane of the present invention is not particularly limited, but in order to improve workability and provide sufficient curability by maintaining the viscosity of the curable composition containing the compound within an appropriate range, the viscosity is preferably 2 to 100,000 mPa s, more preferably 5 to 50,000 mPa s, and particularly preferably 10 to 20,000 mPa s. Here, the viscosity is measured at 25°C using a Brookfield type rotational viscometer.

[0026] The reactive silicon group-containing organopolysiloxane of the present invention can be obtained by subjecting an organopolysiloxane containing silicon-bonded alkenyl groups (hereinafter also referred to as "alkenyl group-containing organopolysiloxane") to a hydrosilylation reaction with a disiloxane compound represented by the following formula (3) in the presence of a platinum group metal catalyst in air or an inert gas such as nitrogen:

[0027] (In the formula, R 1 , R 2 and R 3 has the same meaning as above.)

[0028] Specific examples of the disiloxane compound represented by formula (3) include, but are not limited to, those represented by the following structural formulas: Among these, the disiloxane compound represented by formula (5) is preferred.

[0029]

[0030] The disiloxane compound represented by formula (3) above can be obtained, for example, by subjecting an organoxysilane represented by formula (6) below and a disiloxane compound represented by formula (7) below to an equilibration reaction in the presence of an acid and water.

[0031] (In the formula, R 1 , R 2 and R 3 has the same meaning as above.)

[0032] The siloxane constituent units of the alkenyl group-containing organopolysiloxane are not particularly limited, and the siloxane skeleton may have a linear structure, a branched structure, a cyclic structure, or a crosslinked structure. Specific examples of alkenyl group-containing organopolysiloxanes include 1,1-divinyltetramethyldisiloxane, 1,1,1-trivinyltrimethyldisiloxane, 1,3-divinyltetramethyldisiloxane, 1,3-divinyltetraphenyldisiloxane, 1,3-diallyltetramethyldisiloxane, 1,1,3,3-tetravinyldimethyldisiloxane, hexavinyldisiloxane, 1,3,5,7-tetravinyltetramethylcyclotetrasiloxane, dimethylpolysiloxane containing vinyl groups at both ends, diphenylpolysiloxane containing vinyl groups at both ends, dimethylpolysiloxane / diphenylpolysiloxane copolymer containing vinyl groups at both ends, methylsilicone resin containing vinyl groups at both ends, phenylsilicone resin containing vinyl groups at both ends, and methyl / phenylsilicone resin containing vinyl groups at both ends. From the viewpoint of the mechanical properties of the resulting cured product and the storage stability of the composition, alkenyl group-containing organopolysiloxanes having a linear structure are preferred.

[0033] The alkenyl group is preferably a straight-chain or branched-chain alkenyl group having 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 3-methyl-2-butenyl, and 2-methyl-2-butenyl. nyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 1-methyl-4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, 1-methyl-6-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 5-octenyl, 6-octenyl, 7-octenyl, etc. Among these, a vinyl group or an allyl group is preferred, and a vinyl group is more preferred.

[0034] The number of alkenyl groups contained in one molecule of the alkenyl group-containing organopolysiloxane is one or more, but from the viewpoints of the curability and storage stability of the composition and the mechanical properties of the cured product, the number is preferably two to four, and more preferably two (for example, one at each end of the molecular chain of a linear organopolysiloxane).

[0035] Therefore, the alkenyl group-containing organopolysiloxane is preferably one represented by the following formula (4), and by using such an alkenyl group-containing organopolysiloxane, the mechanical properties of the obtained cured product and the storage stability of the composition are further improved.

[0036] (In the formula, R 4 and p have the same meaning as above.

[0037] In formula (4), R 5 represents an alkenyl group having 2 to 12 carbon atoms. 5The alkenyl group having 2 to 12 carbon atoms is preferably the linear or branched alkenyl group having 2 to 8 carbon atoms exemplified above, more preferably a vinyl group or allyl group, and even more preferably a vinyl group.

[0038] The reaction ratio of the alkenyl group-containing organopolysiloxane with the disiloxane compound represented by formula (3) is preferably such that 0.8 to 2.5 hydrosilyl groups of the disiloxane compound represented by formula (3) per alkenyl group in the alkenyl group-containing organopolysiloxane, and more preferably 0.9 to 2.0 hydrosilyl groups, in order to suppress by-products during the hydrosilylation reaction and to take into consideration the storage stability of the composition and the mechanical properties of the cured product.

[0039] The platinum group metal catalyst used in the hydrosilylation 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, and supported catalysts such as platinum-carbon, platinum-alumina, and platinum-silica. Among these, zero-valent platinum complexes are preferred in terms of selectivity during hydrosilylation, and a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex is more preferred.

[0040] The amount of platinum group metal catalyst used is not particularly limited, but from the standpoints of reactivity, productivity, and the like, it is preferably 0.1 to 1,000 ppm, and more preferably 0.3 to 100 ppm, calculated as the mass of platinum group metal, relative to the total mass of the alkenyl group-containing organopolysiloxane and the disiloxane compound represented by formula (3) above.

[0041] The hydrosilylation reaction can be carried out without a solvent, but a solvent can also be used as needed to the extent that it does not inhibit the reaction. Specific examples of usable solvents 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 of two or more.

[0042] The reaction temperature for the hydrosilylation reaction is not particularly limited, but is preferably 0 to 200°C, more preferably 40 to 110°C, and even more preferably 60 to 100°C. When a solvent is used, the reaction is preferably carried out at a temperature ranging from 0°C to the boiling point of the solvent. The reaction time is not particularly limited, but is usually about 1 to 60 hours, preferably 1 to 24 hours.

[0043] The curable composition of the present invention (hereinafter referred to as the "composition") contains at least the reactive silicon group-containing organopolysiloxane (A) and the curing catalyst (B). Because the composition of the present invention contains the reactive silicon group-containing organopolysiloxane of the present invention, it has excellent curability and provides a cured product that is resistant to yellowing and heat resistance.

[0044] The curing catalyst (B) is a component that promotes the hydrolysis and condensation reaction of the hydrolyzable groups contained in the reactive silicon group-containing organopolysiloxane (A) with moisture in the air, thereby promoting the curing of the composition, and is added to achieve efficient curing. The curing catalyst is not particularly limited as long as it is a curing catalyst that is commonly used for curing moisture-condensation curing compositions. Specific examples thereof include alkyltin compounds such as dibutyltin oxide and dioctyltin oxide; alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctoate, dioctyltin dioctoate, and dioctyltin diversatate; titanate esters and titanium chelate compounds such as tetraisopropoxytitanium, tetra-n-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, dipropoxybis(acetylacetonato)titanium, titanium diisopropoxybis(ethylacetoacetate), and titanium isopropoxyoctylene glycol, as well as partial hydrolysates thereof; zinc naphthenate, zinc stearate, zinc-2-ethyloctoate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, aluminum trihydroxide, aluminum alcoholate, aluminum acylate, aluminum organometallic compounds such as aluminum acylate salts, aluminosiloxy compounds, and aluminum chelate compounds; aminoalkyl group-substituted alkoxysilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, bis[3-(trimethoxysilyl)propyl]amine, bis[3-(triethoxysilyl)propyl]amine, N,N'-bis[3-(trimethoxysilyl)propyl]ethane-1,2-diamine, N,N'-bis[3-(triethoxysilyl)propyl]ethane-1,2-diamine, and N-phenyl-3-aminopropyltrimethoxysilane;amine compounds and salts thereof, such as hexylamine and dodecylamine phosphate; quaternary ammonium salts, such as benzyltriethylammonium acetate; lower fatty acid salts of alkali metals, such as potassium acetate, sodium acetate, and lithium oxalate; dialkylhydroxylamines, such as dimethylhydroxylamine and diethylhydroxylamine; 2-[3-(trimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine, 2-[3-(methyldimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine, 2-[3-(triethoxysilyl)propyl]-1,1, Examples include silanes and siloxanes containing a guanidino group, such as 3,3-tetramethylguanidine, 2-[3-(methyldiethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine, and 2-[3-(tris(trimethylsiloxy)silyl)propyl]-1,1,3,3-tetramethylguanidine; and silanes and siloxanes containing a phosphazene base, such as N,N,N',N',N'',N''-hexamethyl-N'''-[3-(trimethoxysilyl)propyl]-phosphorimidic triamide, which may be used alone or in combination of two or more types.

[0045] Among these, dioctyltin dilaurate, dioctyltin diversatate, tetraisopropoxytitanium, tetra n-butoxytitanium, titanium diisopropoxybis(ethylacetoacetate), 3-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, bis[3-(trimethoxysilyl)propyl]amine, N,N'-bis[3-(trimethoxysilyl)propyl]ethane-1,2-diamine, and 2-[3-(trimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine are preferred because of their excellent reactivity, and further, From the viewpoint of the curability of the composition, dioctyltin dilaurate, dioctyltin diversatate, 3-aminopropyltrimethoxysilane, and 2-[3-(trimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine are more preferred, and from the viewpoint of not containing an organotin compound and being less toxic, 3-aminopropyltrimethoxysilane and 2-[3-(trimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine are even more preferred, and from the viewpoint of the curability of the composition, 2-[3-(trimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine is particularly preferred.

[0046] The amount of curing catalyst added is not particularly limited, but in order to adjust the curing rate within an appropriate range and improve workability, it is preferably 0.01 to 15 parts by mass, and more preferably 0.1 to 5 parts by mass, per 100 parts by mass of (A) the reactive silicon group-containing organopolysiloxane.

[0047] Furthermore, for the purpose of adjusting the viscosity of the composition of the present invention to improve workability, or for the purpose of adjusting the curability of the composition or the hardness and flexibility of the resulting coating film, one or more compounds selected from silane compounds containing alkoxysilyl groups, silicone alkoxy oligomers containing alkoxysilyl groups and / or silanol groups in one molecule, and silicone resins other than the reactive silicon group-containing organopolysiloxane of component (A), may be added depending on the intended use.

[0048] The silane compound containing an alkoxysilyl group is not particularly limited, and specific examples thereof include tetraalkoxysilanes such as tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetraisopropoxysilane, tetrabutoxysilane, and tetraoctoxysilane; trialkoxysilanes such as methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, nonafluorohexyltrimethoxysilane, tridecafluorooctyltrimethoxysilane, and polyethylene glycol methyl-3-trimethoxysilylpropyl ether; Examples of the alkoxysilane include dialkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, diphenyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycidoxypropylmethyldiethoxysilane; and monoalkoxysilanes such as trimethylmethoxysilane, trimethylethoxysilane, vinyldimethylmethoxysilane, 3-methacryloxypropyldimethylmethoxysilane, 3-methacryloxypropyldimethylethoxysilane, 3-acryloxypropyldimethylmethoxysilane, 3-acryloxypropyldimethylethoxysilane, N-2-(aminoethyl)-3-aminopropyldimethylmethoxysilane, and N-2-(aminoethyl)-3-aminopropyldimethylethoxysilane.

[0049] The silicone alkoxy oligomer having an alkoxysilyl group and / or a silanol group per molecule is not particularly limited, and may be a commercially available product. Specific examples thereof include X-40-9250, X-40-9246, X-40-9225, KR-500, KR-515, KC-89S, KR-401N, X-40-9227, KR-510, KR-9218, KR-400, X-40-2327, and KR-401 manufactured by Shin-Etsu Chemical Co., Ltd. Furthermore, the silicone resin is not particularly limited, and may be a commercially available product. Specific examples thereof include KR-220L, KR-251, KR-112, KR-300, KR-311, KR-480, and KR-216 manufactured by Shin-Etsu Chemical Co., Ltd.

[0050] Furthermore, the composition of the present invention is preferably a solvent-free form that does not substantially contain organic solvents (which are often harmful to humans and flammable), but a solvent may be added depending on the intended use and workability. Here, "substantially" means that the solvent contained in the composition is 1% by mass or less, particularly 0.1% by mass or less. The solvent is not particularly limited as long as it dissolves component (A), but specific examples include hydrocarbon solvents such as pentane, hexane, heptane, octane, decane, and cyclohexane; aromatic solvents such as benzene, toluene, and xylene; amide solvents such as formamide, N,N-dimethylformamide, pyrrolidone, and N-methylpyrrolidone; ester solvents such as ethyl acetate, butyl acetate, γ-butyrolactone, and propylene glycol-1-monomethyl ether-2-acetate; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; and ether solvents such as diethyl ether, dibutyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane, which may be used alone or in combination of two or more. Among these, aromatic solvents such as toluene and xylene are preferred from the viewpoints of solubility and volatility.

[0051] Depending on the intended use, various additives such as adhesion improvers, inorganic and organic ultraviolet absorbers, storage stability improvers, plasticizers, fillers, pigments, and fragrances may be added to the composition of the present invention.

[0052] A coated solid substrate can be obtained by applying the composition of the present invention described above to the surface of a solid substrate and curing it to form a coating layer, and an adhesive laminate can be obtained by applying the adhesive composition of the present invention to the surface of a solid substrate, laminating another solid substrate thereon, and then curing the composition to form an adhesive layer. The method for applying the composition is not particularly limited, and specific examples thereof can be appropriately selected from known methods such as spray coating, spin coating, dip coating, roller coating, brush coating, bar coating, and flow coating.

[0053] The material and shape of the solid substrate are not particularly limited, and specific examples thereof include organic resin substrates such as epoxy resin, phenol resin, polyimide resin, polycarbonate resin such as polycarbonates and polycarbonate blends, acrylic resin such as poly(methyl methacrylate), polyester resin such as poly(ethylene terephthalate), poly(butylene terephthalate), unsaturated polyester resin, polyamide resin, acrylonitrile-styrene copolymer resin, styrene-acrylonitrile-butadiene copolymer resin, polyvinyl chloride resin, polystyrene resin, blends of polystyrene and polyphenylene ether, cellulose acetate butyrate, and polyethylene resin; metal substrates such as iron plate, copper plate, and steel plate; painted surfaces; glass; ceramic; concrete; slate; textile; wood, stone, roof tile, (hollow) inorganic fillers such as silica, titania, zirconia, and alumina; and glass fiber products such as glass fiber, glass cloth, glass tape, glass mat, and glass paper.

[0054] When the composition of the present invention comes into contact with moisture in the atmosphere, the hydrolysis and condensation reaction of the reactive silicon group-containing organopolysiloxane (A) proceeds. The moisture content of the atmosphere can be measured using any humidity between 10 and 100% RH. Generally, the higher the humidity, the faster the hydrolysis proceeds, so moisture can be added to the atmosphere if desired. The curing reaction temperature and time can be adjusted appropriately depending on factors such as the substrate used, moisture concentration, catalyst concentration, and type of hydrolyzable group. From the standpoint of workability, the curing reaction temperature is typically preferably about 10°C to 40°C. However, to accelerate the curing reaction, the composition may be heated to a temperature not exceeding the heat resistance temperature of the substrate used. The curing reaction time is typically about one minute to one week, from the standpoint of workability, etc.

[0055] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following, the viscosity is measured at 25°C using a B-type rotational viscometer, and the molecular weight and degree of polymerization are number-average molecular weight and number-average degree of polymerization in terms of polystyrene determined by GPC (gel permeation chromatography) measurement.

[0056] [1] Synthesis of disiloxane compound [Example 1-1] Synthesis of disiloxane compound a

[0057] A 300 mL separable flask equipped with a stirrer, reflux condenser, and thermometer was charged with 200 g of trimethoxy(methoxymethyl)silane and 40.4 g of 1,1,3,3-tetramethyldisiloxane, and 1.2 g of concentrated sulfuric acid (98% by mass) was added dropwise with stirring at 7°C. After completion of the dropwise addition, the mixture was stirred for 5 hours at 25°C. Thereafter, 6 g of Kyoward (registered trademark) 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added, and after stirring for 1 hour, the reaction liquid was removed by filtration and distilled (distillation temperature 90°C, vacuum degree 17 kPa) to obtain disiloxane compound a. 1 H-NMR (CDCl3): δ4.46-4.61ppm (s, 1H, -SiH), 3.41-3.34ppm (s, 9H, -Si(OC H3)2, -OCH3), 3.15-3.13ppm (s, 2H, -CH2-), 0.00-0.02ppm (s, 6H, -SiCH3)

[0058] [Example 1-2] Synthesis of disiloxane compound b

[0059] A 300 mL separable flask equipped with a stirrer, reflux condenser, and thermometer was charged with 268 g of triethoxy(ethoxymethyl)silane and 40.4 g of 1,1,3,3-tetramethyldisiloxane, and 1.2 g of concentrated sulfuric acid (98% by mass) was added dropwise with stirring at 7°C. After completion of the dropwise addition, the mixture was stirred for 5 hours at 25°C. Thereafter, 6 g of Kyoward (registered trademark) 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added, and after stirring for 1 hour, the reaction liquid was removed by filtration and distilled (distillation temperature 90°C, vacuum degree 17 kPa) to obtain disiloxane compound b. 1 H-NMR (CDCl3): δ4.46-4.61ppm (s, 1H, -SiH), 3.85-3.63ppm (m, 6H, -OCH2-), 1.41-1.34ppm (m, 9H, -CH3), 0.00-0.02ppm (s, 6H, -SiCH3)

[0060] [Example 1-3] Synthesis of disiloxane compound c

[0061] A 300 mL separable flask equipped with a stirrer, reflux condenser, and thermometer was charged with 200 g of trimethoxy(methoxymethyl)silane and 115 g of 1,1,3,3-tetraphenyldisiloxane, and 1.2 g of concentrated sulfuric acid (98% by mass) was added dropwise with stirring at 7°C. After completion of the dropwise addition, the mixture was stirred for 5 hours at 25°C. Thereafter, 6 g of Kyoward (registered trademark) 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added, and after stirring for 1 hour, the reaction liquid was removed by filtration and distilled (distillation temperature 90°C, vacuum degree 17 kPa) to obtain disiloxane compound c. 1 H-NMR (CDCl3): δ7.58-7.32ppm (m, 10H, -SiC6H5), 4.46-4.61ppm (s, 1H, -Si H), 3.41 to 3.34 ppm (s, 9H, -Si(OCH3)2, -OCH3), 3.15 to 3.13 ppm (s, 2H, -CH2-)

[0062] [2] Synthesis of Reactive Silicon Group-Containing Organopolysiloxanes [Example 2-1] Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A-1 100 g (0.015 mol in terms of vinyl groups) of a dimethylpolysiloxane capped at both ends with vinyldimethylsiloxy groups and having a number average molecular weight of 13,600 and a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (50 ppm as platinum) were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and the mixture was heated to 60° C. 7.36 g (0.030 mol in terms of hydrosilyl groups) of disiloxane compound a was added, and the mixture was stirred at 60° C. for 2 hours. 1 The reaction was deemed complete when H-NMR analysis confirmed that the peaks derived from the vinyl groups of the raw material had completely disappeared and that peaks derived from the target product had been detected. After completion of the reaction, the solvent was distilled off at 100°C and a vacuum of 1.3 kPa for 3 hours to obtain reactive silicon group-containing organopolysiloxane A-1. The resulting reactive silicon group-containing organopolysiloxane A-1 was a colorless, transparent liquid with a number average molecular weight of 15,000 and a viscosity of 610 mPa s.

[0063] Example 2-2 Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A-2 100 g (0.0051 mol in terms of vinyl groups) of a dimethylpolysiloxane capped at both ends with vinyldimethylsiloxy groups and having a number average molecular weight of 39,900 and a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (50 ppm as platinum) were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and heated to 60° C. 2.50 g (0.03 mol in terms of hydrosilyl groups) of disiloxane compound a was added, and the mixture was stirred at 60° C. for 2 hours. 1 The reaction was deemed complete when H-NMR analysis confirmed that the peaks derived from the vinyl groups of the raw material had completely disappeared and that peaks derived from the target product had been detected. After completion of the reaction, the solvent was distilled off at 100°C and a vacuum of 1.3 kPa for 3 hours to obtain reactive silicon group-containing organopolysiloxane A-2. The resulting reactive silicon group-containing organopolysiloxane A-2 was a colorless, transparent liquid with a number average molecular weight of 41,500 and a viscosity of 11,000 mPa s.

[0064] Example 2-3 Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A-3 100 g (0.015 mol in terms of vinyl groups) of a dimethylpolysiloxane capped at both ends with vinyldimethylsiloxy groups and having a number average molecular weight of 13,600 and a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (50 ppm as platinum) were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and heated to 60° C. 9.00 g (0.030 mol in terms of hydrosilyl groups) of disiloxane compound b was added, and the mixture was stirred at 60° C. for 2 hours. 1 The reaction was deemed complete when H-NMR analysis confirmed that the peaks derived from the vinyl groups of the raw material had completely disappeared and that peaks derived from the target product had been detected. After completion of the reaction, the solvent was distilled off at 100°C and a vacuum of 1.3 kPa for 3 hours to obtain reactive silicon group-containing organopolysiloxane A-3. The resulting reactive silicon group-containing organopolysiloxane A-3 was a colorless, transparent liquid with a number average molecular weight of 15,200 and a viscosity of 620 mPa s.

[0065] Example 2-4 Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A-4 100 g (0.015 mol in terms of vinyl groups) of a dimethylpolysiloxane capped at both ends with vinyldimethylsiloxy groups and having a number average molecular weight of 13,600 and a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (50 ppm as platinum) were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and heated to 60° C. 9.70 g (0.030 mol in terms of hydrosilyl groups) of disiloxane compound c was added, and the mixture was stirred at 60° C. for 2 hours. 1 The reaction was deemed complete when H-NMR analysis confirmed that the peaks derived from the vinyl groups of the raw material had completely disappeared and that peaks derived from the target product had been detected. After completion of the reaction, the solvent was distilled off at 100°C and a vacuum of 1.3 kPa for 3 hours to obtain reactive silicon group-containing organopolysiloxane A-4. The resulting reactive silicon group-containing organopolysiloxane A-4 was a colorless, transparent liquid with a number average molecular weight of 15,500 and a viscosity of 620 mPa s.

[0066] Comparative Example 2-1 Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A'-5 100 g (0.015 mol in terms of vinyl groups) of a dimethylpolysiloxane capped at both ends with vinyldimethylsiloxy groups and having a number average molecular weight of 13,600 and a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (50 ppm as platinum) were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and heated to 60° C. 3.18 g (0.030 mol in terms of hydrosilyl groups) of methyldimethoxysilane was added, and the mixture was stirred at 60° C. for 2 hours. 1 The reaction was deemed complete when H-NMR analysis confirmed that the peaks derived from the vinyl groups of the raw material had completely disappeared and that peaks derived from the target product had been detected. After completion of the reaction, the solvent was distilled off at 100°C and 1.3 kPa for 3 hours to yield reactive silicon group-containing organopolysiloxane A'-5. The resulting reactive silicon group-containing organopolysiloxane A'-5 was a colorless, transparent liquid with a number average molecular weight of 15,500 and a viscosity of 620 mPa s.

[0067] Comparative Example 2-2 Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A'-6 100 g (0.015 mol in terms of vinyl groups) of a dimethylpolysiloxane capped at both ends with vinyldimethylsiloxy groups and having a number average molecular weight of 13,600 and 2.54 g (0.015 mol in terms of mercapto groups) of mercaptomethyltrimethoxysilane were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and heated to 90° C. 0.1 g of 2,2'-azobis-2-methylbutyronitrile was added, and the mixture was stirred at 90° C. for 3 hours. 1 The reaction was terminated when H-NMR analysis confirmed that the peaks derived from the vinyl and mercapto groups of the raw materials had completely disappeared and that the peaks derived from the target product had been detected. The resulting reactive silicon group-containing organopolysiloxane A'-6 was a colorless, transparent liquid with a number average molecular weight of 15,900 and a viscosity of 550 mPa s.

[0068] Comparative Example 2-3 Synthesis of Reactive Silicon Group-Containing Organopolysiloxane A'-7 100 g (0.040 mol equivalent to hydroxyl groups) of polypropylene glycol having a number average molecular weight of 7,600 and hydroxyl groups at both ends and 7.1 g (0.040 mol equivalent to isocyanatomethyltrimethoxysilane) were placed in a 200 mL separable flask equipped with a stirrer, reflux condenser, and thermometer, and heated to 80°C. 0.1 g of dioctyltin dilaurate was added thereto, and the mixture was stirred at 80°C for 3 hours. IR measurement confirmed that the absorption peaks derived from the isocyanato groups of the raw material had completely disappeared, and that an absorption peak derived from the urethane bond had been detected, marking the end of the reaction. The resulting reactive silicon group-containing organopolysiloxane A'-7 was a pale yellow, transparent liquid with a number average molecular weight of 8,000 and a viscosity of 3,700 mPa·s.

[0069] [3] Preparation of Composition and Cured Coating [Example 3-1] A composition was prepared by uniformly mixing 100 parts by mass of the reactive silicon group-containing organopolysiloxane A-1 obtained in Example 2-1 above and 0.5 parts by mass of curing catalyst B-1 (2-[3-(trimethoxysilyl)propyl]-1,1,3,3-tetramethylguanidine) using a stirrer while keeping the mixture protected from moisture. The resulting composition was applied to a glass plate using a No. 14 bar coater in air at 25°C and 50% RH, and then dried and cured for one day in air at 25°C and 50% RH to produce a cured coating.

[0070] Examples 3-2 to 3-4 and Comparative Examples 3-1 to 3-3 Compositions and cured coatings were prepared in the same manner as in Example 3-1, except that the reactive silicon group-containing organopolysiloxane A-1 in Example 3-1 was replaced with the reactive silicon group-containing organopolysiloxanes A-2 to A-4 obtained in Examples 2-2 to 2-4 and the reactive silicon group-containing organopolysiloxanes A'-5 to A'-7 obtained in Comparative Examples 2-1 to 2-3, respectively.

[0071] Example 3-5 A composition and a cured coating were prepared in the same manner as in Example 3-1, except that the curing catalyst B-1 in Example 3-1 was changed to 5 parts by mass of curing catalyst B-2 (3-aminopropyltrimethoxysilane).

[0072] Example 3-6 A composition and a cured coating were prepared in the same manner as in Example 3-1, except that the curing catalyst B-1 in Example 3-1 was changed to 5 parts by mass of curing catalyst B-3 (dioctyltin diversatate).

[0073] Example 3-7 A composition and a cured coating were prepared in the same manner as in Example 3-1, except that the curing catalyst B-1 in Example 3-1 was changed to 2 parts by mass of curing catalyst B-4 (titanium diisopropoxybis(ethylacetoacetate)).

[0074] Comparative Example 3-4 A composition and a cured coating were prepared in the same manner as in Comparative Example 3-1, except that the curing catalyst B-1 in Comparative Example 3-1 was changed to 5 parts by mass of curing catalyst B-2 (3-aminopropyltrimethoxysilane).

[0075] Comparative Example 3-5 A composition and a cured coating were prepared in the same manner as in Comparative Example 3-1, except that the curing catalyst B-1 in Comparative Example 3-1 was changed to 5 parts by mass of curing catalyst B-3 (dioctyltin diversatate).

[0076] Comparative Example 3-6 A composition and a cured coating were prepared in the same manner as in Comparative Example 3-2, except that the curing catalyst B-1 in Comparative Example 3-2 was changed to 5 parts by mass of curing catalyst B-2 (3-aminopropyltrimethoxysilane).

[0077] Comparative Example 3-7 A composition and a cured coating were prepared in the same manner as in Comparative Example 3-2, except that the curing catalyst B-1 in Comparative Example 3-2 was changed to 5 parts by mass of curing catalyst B-3 (dioctyltin diversatate).

[0078] The cured coatings produced in Examples 3-1 to 3-7 and Comparative Examples 3-1 to 2-7 above were evaluated for the following physical properties. The results are shown in Tables 1 and 2. [Tack-free time] Test specimens obtained by applying the composition to glass plates using the above application method were left in an atmosphere of 25°C and 50% RH, and the time until the coating no longer adheres to the finger when pressed with a finger on the coated surface due to the progress of moisture curing was measured. A smaller value indicates better curability. [Yellowing resistance] Test specimens formed on glass plates using the above application method were irradiated with ultraviolet light (cumulative exposure dose 26,000 mJ / cm) for 2 weeks using a germicidal lamp in an atmosphere of 25°C and 50% RH. 3 ) was performed. The degree of yellowing of the cured coating at this time was evaluated using a color difference meter in accordance with JIS K 7373 as ΔYI (yellowing index = change in yellowness index YI). A smaller value indicates better yellowing resistance. A ΔYI of less than 0.5 was evaluated as excellent yellowing resistance and was rated as "○". A ΔYI of 0.5 or more was evaluated as "×". [Heat Resistance] Test specimens on glass plates on which cured coatings had been formed by the above coating method were left to stand in a dryer at 150°C for two weeks. After that, coatings that did not leave a finger mark when pressed with a finger on the surface were evaluated as "○". Coatings that left a finger mark when pressed with a finger on the surface were evaluated as "×".

[0079]

[0080]

[0081] As shown in Table 1, the cured coatings produced in Examples 3-1 to 3-7 using the reactive silicon group-containing organopolysiloxanes A-1 to A-4 obtained in Examples 2-1 to 2-4 were found to have excellent curability, yellowing resistance, and heat resistance. On the other hand, as shown in Table 2, Comparative Examples 3-1, 3-4, and 3-5, which used organopolysiloxane A'-5, which did not have a group represented by structural formula (1), exhibited poor curability, Comparative Examples 3-2, 3-6, and 3-7, which used organopolysiloxane A'-6 having a sulfide-methylene-silicon bond, exhibited low heat resistance, and Comparative Example 3-3, which used organopolysiloxane A'-7 having a urethane bond, exhibited poor yellowing resistance.

Claims

1. A reactive silicon group-containing organopolysiloxane having one or more groups represented by the following structural formula (1) bonded to silicon atoms in one molecule. (In the formula, R 1 and R 2 each independently represent a hydrogen atom, an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and R 3 each independently represent an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and n is an integer of 2 to 12. The wavy line represents a bond.) 2. The reactive silicon group-containing organopolysiloxane according to claim 1, represented by the following formula (2). (In the formula, R 1 , R 2 , R 3 and n represent the same meanings as described above, and R 4 each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and p is an integer of 1 to 2,000.) 3. A disiloxane compound represented by the following formula (3). (In the formula, R 1 and R 2 are each independently a hydrogen atom, an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and R 3 are each independently an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.) 4. The method for producing a reactive silicon group-containing organopolysiloxane according to claim 1, wherein an alkenyl group-containing organopolysiloxane bonded to a silicon atom is subjected to a hydrosilylation reaction with a disiloxane compound represented by the following formula (3). (In the formula, R 1 , R 2 and R 3 represent the same meaning as described above.) 5. The method for producing a reactive silicon group-containing organopolysiloxane according to claim 4, wherein the organopolysiloxane containing an alkenyl group bonded to the silicon atom is represented by the following formula (4). (In the formula, R 4 each independently represents an aliphatic saturated hydrocarbon group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and R 5 represents an alkenyl group having 2 to 12 carbon atoms, and p is an integer of 1 to 2000.) 6. A curable composition containing (A) a reactive silicon group-containing organopolysiloxane according to claim 1 and (B) a curing catalyst.

7. The curable composition according to claim 6, wherein the (B) curing catalyst is an amine compound.

8. A cured product obtained by curing the curable composition according to claim 6 or 7.

9. A coating agent composition containing (A) a reactive silicon group-containing organopolysiloxane according to claim 1 and (B) a curing catalyst.

10. The coating agent composition according to claim 9, wherein the (B) curing catalyst is an amine compound.

11. An article having a coating layer obtained by curing the coating agent composition according to claim 9 or 10.

12. An adhesive composition containing (A) a reactive silicon group-containing organopolysiloxane according to claim 1 and (B) a curing catalyst.

13. The adhesive composition according to claim 12, wherein the (B) curing catalyst is an amine compound.

14. An article having an adhesive layer obtained by curing the adhesive composition according to claim 12 or 13.

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